JP4483344B2 - シルセスキオキサン骨格を有する化合物およびその重合体 - Google Patents
シルセスキオキサン骨格を有する化合物およびその重合体 Download PDFInfo
- Publication number
- JP4483344B2 JP4483344B2 JP2004053219A JP2004053219A JP4483344B2 JP 4483344 B2 JP4483344 B2 JP 4483344B2 JP 2004053219 A JP2004053219 A JP 2004053219A JP 2004053219 A JP2004053219 A JP 2004053219A JP 4483344 B2 JP4483344 B2 JP 4483344B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- acid
- replaced
- oco
- coo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 161
- 229920000642 polymer Polymers 0.000 title claims description 62
- -1 1,4-phenylene, 1,3-dioxane-2,5-diyl Chemical group 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000002947 alkylene group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 229920005575 poly(amic acid) Polymers 0.000 claims description 19
- 239000010409 thin film Substances 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 16
- 239000002966 varnish Substances 0.000 claims description 15
- 150000008064 anhydrides Chemical group 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 10
- 229920000728 polyester Polymers 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000004642 Polyimide Substances 0.000 claims description 7
- 229920001721 polyimide Polymers 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 239000004033 plastic Substances 0.000 claims description 4
- 229920003023 plastic Polymers 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 42
- 239000002904 solvent Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000002253 acid Substances 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 150000004985 diamines Chemical class 0.000 description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 13
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 150000004820 halides Chemical class 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 229920000620 organic polymer Polymers 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 6
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 239000012156 elution solvent Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 4
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 150000004714 phosphonium salts Chemical class 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- DJOGGVVIZHGION-UHFFFAOYSA-N 1-nitro-4-prop-2-enoxybenzene Chemical compound [O-][N+](=O)C1=CC=C(OCC=C)C=C1 DJOGGVVIZHGION-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010292 electrical insulation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 3
- QKKWJYSVXDGOOJ-UHFFFAOYSA-N oxalic acid;oxotitanium Chemical class [Ti]=O.OC(=O)C(O)=O QKKWJYSVXDGOOJ-UHFFFAOYSA-N 0.000 description 3
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- JEAQJTYJUMGUCD-UHFFFAOYSA-N 3,4,5-triphenylphthalic acid Chemical compound C=1C=CC=CC=1C=1C(C=2C=CC=CC=2)=C(C(O)=O)C(C(=O)O)=CC=1C1=CC=CC=C1 JEAQJTYJUMGUCD-UHFFFAOYSA-N 0.000 description 2
- ZYEDGEXYGKWJPB-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)(C)C1=CC=C(N)C=C1 ZYEDGEXYGKWJPB-UHFFFAOYSA-N 0.000 description 2
- QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-UHFFFAOYSA-N 0.000 description 2
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 2
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 description 2
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical compound OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 2
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 125000006160 pyromellitic dianhydride group Chemical group 0.000 description 2
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- BCGPZCSDYLUCTL-UHFFFAOYSA-N trimethylsilyl pent-4-enoate Chemical compound C[Si](C)(C)OC(=O)CCC=C BCGPZCSDYLUCTL-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 239000013585 weight reducing agent Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- QLMQETZMAZOZRM-UHFFFAOYSA-N (4-hydroxy-2,3-diphenylphenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 QLMQETZMAZOZRM-UHFFFAOYSA-N 0.000 description 1
- AAFXQFIGKBLKMC-KQQUZDAGSA-N (e)-3-[4-[(e)-2-carboxyethenyl]phenyl]prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=C(\C=C\C(O)=O)C=C1 AAFXQFIGKBLKMC-KQQUZDAGSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- CEGRHPCDLKAHJD-UHFFFAOYSA-N 1,1,1-propanetricarboxylic acid Chemical compound CCC(C(O)=O)(C(O)=O)C(O)=O CEGRHPCDLKAHJD-UHFFFAOYSA-N 0.000 description 1
- FBZVZUSVGKOWHG-UHFFFAOYSA-N 1,1-dimethoxy-n,n-dimethylethanamine Chemical compound COC(C)(OC)N(C)C FBZVZUSVGKOWHG-UHFFFAOYSA-N 0.000 description 1
- DVGGYXXTNYZERM-UHFFFAOYSA-N 1,2,5-oxadiazole-3,4-dicarboxylic acid Chemical compound OC(=O)C1=NON=C1C(O)=O DVGGYXXTNYZERM-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- HFHARFNUBJTTGI-UHFFFAOYSA-N 1,3-thiazole-4,5-dicarboxylic acid Chemical compound OC(=O)C=1N=CSC=1C(O)=O HFHARFNUBJTTGI-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- UTYAEKVPLFDTTI-UHFFFAOYSA-N 1,4-dioxoanthracene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(C(C(=O)O)=C(C(O)=O)C3=O)=O)C3=CC2=C1 UTYAEKVPLFDTTI-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 1
- GBURUDXSBYGPBL-UHFFFAOYSA-N 2,2,3-trimethylhexanedioic acid Chemical compound OC(=O)C(C)(C)C(C)CCC(O)=O GBURUDXSBYGPBL-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- WKRCUUPMCASSBN-UHFFFAOYSA-N 2,2-diethylbutanedioic acid Chemical compound CCC(CC)(C(O)=O)CC(O)=O WKRCUUPMCASSBN-UHFFFAOYSA-N 0.000 description 1
- BTUDGPVTCYNYLK-UHFFFAOYSA-N 2,2-dimethylglutaric acid Chemical compound OC(=O)C(C)(C)CCC(O)=O BTUDGPVTCYNYLK-UHFFFAOYSA-N 0.000 description 1
- WCZNKVPCIFMXEQ-UHFFFAOYSA-N 2,3,5,6-tetramethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=C(C)C(C)=C1N WCZNKVPCIFMXEQ-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 description 1
- FKUJGZJNDUGCFU-UHFFFAOYSA-N 2,5-dimethylterephthalic acid Chemical compound CC1=CC(C(O)=O)=C(C)C=C1C(O)=O FKUJGZJNDUGCFU-UHFFFAOYSA-N 0.000 description 1
- XQIBGVDOSWYGGA-UHFFFAOYSA-N 2,5-dioxobicyclo[2.2.2]octane-1,4-dicarboxylic acid Chemical compound C1CC2(C(O)=O)CC(=O)C1(C(=O)O)CC2=O XQIBGVDOSWYGGA-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- JZUMVFMLJGSMRF-UHFFFAOYSA-N 2-Methyladipic acid Chemical compound OC(=O)C(C)CCCC(O)=O JZUMVFMLJGSMRF-UHFFFAOYSA-N 0.000 description 1
- MXPYJVUYLVNEBB-UHFFFAOYSA-N 2-[2-(2-carboxybenzoyl)oxycarbonylbenzoyl]oxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(O)=O MXPYJVUYLVNEBB-UHFFFAOYSA-N 0.000 description 1
- UTENGZNBNPABQE-UHFFFAOYSA-N 2-[3-(carboxymethyl)-1-adamantyl]acetic acid Chemical compound C1C(C2)CC3CC1(CC(=O)O)CC2(CC(O)=O)C3 UTENGZNBNPABQE-UHFFFAOYSA-N 0.000 description 1
- SLWIPPZWFZGHEU-UHFFFAOYSA-N 2-[4-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=C(CC(O)=O)C=C1 SLWIPPZWFZGHEU-UHFFFAOYSA-N 0.000 description 1
- YUZSJKBFHATJHV-UHFFFAOYSA-N 2-[4-[2-[4-(2-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C(=CC=CC=3)N)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 YUZSJKBFHATJHV-UHFFFAOYSA-N 0.000 description 1
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- FESCCKVVOSPLPW-UHFFFAOYSA-N 2-amino-5-[2-(4-amino-3-sulfamoylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzenesulfonamide Chemical compound C1=C(S(N)(=O)=O)C(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C(S(N)(=O)=O)=C1 FESCCKVVOSPLPW-UHFFFAOYSA-N 0.000 description 1
- ONNHGWICTXQULH-UHFFFAOYSA-N 2-amino-5-[4-[2-[4-(4-amino-3-carbamoylphenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]benzamide Chemical compound C1=C(N)C(C(=O)N)=CC(OC=2C=CC(=CC=2)C(C=2C=CC(OC=3C=C(C(N)=CC=3)C(N)=O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 ONNHGWICTXQULH-UHFFFAOYSA-N 0.000 description 1
- PCIQYJOYHNJHHC-UHFFFAOYSA-N 2-amino-5-[4-[2-[4-(4-amino-3-carboxyphenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C=C(C(N)=CC=3)C(O)=O)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 PCIQYJOYHNJHHC-UHFFFAOYSA-N 0.000 description 1
- FVTCFQMGXTWDQX-UHFFFAOYSA-N 2-amino-5-[4-[2-[4-(4-amino-3-sulfamoylphenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]benzenesulfonamide Chemical compound C1=C(S(N)(=O)=O)C(N)=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C=C(C(N)=CC=3)S(N)(=O)=O)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 FVTCFQMGXTWDQX-UHFFFAOYSA-N 0.000 description 1
- AQHFCRYZABKUEV-UHFFFAOYSA-N 2-chloro-5-methoxybenzoic acid Chemical compound COC1=CC=C(Cl)C(C(O)=O)=C1 AQHFCRYZABKUEV-UHFFFAOYSA-N 0.000 description 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- VSZJLXSVGVDPMJ-UHFFFAOYSA-N 2-phenylterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C=2C=CC=CC=2)=C1 VSZJLXSVGVDPMJ-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- QVNDSQQNODQYJM-UHFFFAOYSA-N 3,4-diphenylcyclobutane-1,2-dicarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C=2C=CC=CC=2)C1C1=CC=CC=C1 QVNDSQQNODQYJM-UHFFFAOYSA-N 0.000 description 1
- GTALYBOAEVNYOZ-UHFFFAOYSA-N 3-(2,3-dicarboxycyclohexyl)cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1C(C(=O)O)CCCC1C1C(C(O)=O)C(C(O)=O)CCC1 GTALYBOAEVNYOZ-UHFFFAOYSA-N 0.000 description 1
- OLQWMCSSZKNOLQ-UHFFFAOYSA-N 3-(2,5-dioxooxolan-3-yl)oxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-UHFFFAOYSA-N 0.000 description 1
- LXJLFVRAWOOQDR-UHFFFAOYSA-N 3-(3-aminophenoxy)aniline Chemical compound NC1=CC=CC(OC=2C=C(N)C=CC=2)=C1 LXJLFVRAWOOQDR-UHFFFAOYSA-N 0.000 description 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 1
- SYDXFBKNEAFAEN-UHFFFAOYSA-N 3-(4-propylphenyl)aniline Chemical compound C1=CC(CCC)=CC=C1C1=CC=CC(N)=C1 SYDXFBKNEAFAEN-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- RHRNYXVSZLSRRP-UHFFFAOYSA-N 3-(carboxymethyl)cyclopentane-1,2,4-tricarboxylic acid Chemical compound OC(=O)CC1C(C(O)=O)CC(C(O)=O)C1C(O)=O RHRNYXVSZLSRRP-UHFFFAOYSA-N 0.000 description 1
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 1
- CKOFBUUFHALZGK-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC(CC=2C=C(N)C=CC=2)=C1 CKOFBUUFHALZGK-UHFFFAOYSA-N 0.000 description 1
- NBMISTBWISXDGK-UHFFFAOYSA-N 3-[2-[4-[2-(3-aminophenyl)ethyl]phenyl]ethyl]aniline Chemical compound NC1=CC=CC(CCC=2C=CC(CCC=3C=C(N)C=CC=3)=CC=2)=C1 NBMISTBWISXDGK-UHFFFAOYSA-N 0.000 description 1
- IRESXNMNAGCVLK-UHFFFAOYSA-N 3-[3-(2,3-dicarboxy-4,5,6-triphenylphenyl)phenyl]-4,5,6-triphenylphthalic acid Chemical compound C=1C=CC=CC=1C=1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C(=O)O)=C(C(O)=O)C=1C(C=1)=CC=CC=1C(C(=C1C=2C=CC=CC=2)C=2C=CC=CC=2)=C(C(O)=O)C(C(O)=O)=C1C1=CC=CC=C1 IRESXNMNAGCVLK-UHFFFAOYSA-N 0.000 description 1
- TVOXGJNJYPSMNM-UHFFFAOYSA-N 3-[4-(2,3-dicarboxy-4,5,6-triphenylphenyl)phenyl]-4,5,6-triphenylphthalic acid Chemical compound C=1C=CC=CC=1C=1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C(=O)O)=C(C(O)=O)C=1C(C=C1)=CC=C1C(C(=C1C=2C=CC=CC=2)C=2C=CC=CC=2)=C(C(O)=O)C(C(O)=O)=C1C1=CC=CC=C1 TVOXGJNJYPSMNM-UHFFFAOYSA-N 0.000 description 1
- MFTFTIALAXXIMU-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)C(C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MFTFTIALAXXIMU-UHFFFAOYSA-N 0.000 description 1
- DYEYOOADMDSIGQ-UHFFFAOYSA-N 3-[[4-[(3-aminophenyl)methyl]phenyl]methyl]aniline Chemical compound NC1=CC=CC(CC=2C=CC(CC=3C=C(N)C=CC=3)=CC=2)=C1 DYEYOOADMDSIGQ-UHFFFAOYSA-N 0.000 description 1
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 description 1
- CNWZDXMFPRCFFL-UHFFFAOYSA-N 3-[dichloro(methyl)silyl]propyl acetate Chemical compound CC(=O)OCCC[Si](C)(Cl)Cl CNWZDXMFPRCFFL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WUMMIJWEUDHZCL-UHFFFAOYSA-N 3-prop-2-enyloxolane-2,5-dione Chemical compound C=CCC1CC(=O)OC1=O WUMMIJWEUDHZCL-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- WECDUOXQLAIPQW-UHFFFAOYSA-N 4,4'-Methylene bis(2-methylaniline) Chemical compound C1=C(N)C(C)=CC(CC=2C=C(C)C(N)=CC=2)=C1 WECDUOXQLAIPQW-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- OPQVOOASZKDKBH-UHFFFAOYSA-N 4,8-dioxoadamantane-1,3-dicarboxylic acid Chemical compound C1C(C2=O)CC3CC2(C(O)=O)CC1(C(=O)O)C3=O OPQVOOASZKDKBH-UHFFFAOYSA-N 0.000 description 1
- MUMLTWQOPLOPJF-UHFFFAOYSA-N 4-(2,2-diphenylpropyl)phthalic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C)CC1=CC=C(C(O)=O)C(C(O)=O)=C1 MUMLTWQOPLOPJF-UHFFFAOYSA-N 0.000 description 1
- LFEWXDOYPCWFHR-UHFFFAOYSA-N 4-(4-carboxybenzoyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C=C1 LFEWXDOYPCWFHR-UHFFFAOYSA-N 0.000 description 1
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- SQJQLYOMPSJVQS-UHFFFAOYSA-N 4-(4-carboxyphenyl)sulfonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 SQJQLYOMPSJVQS-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- UNHOIPHYTXGJQL-UHFFFAOYSA-N 4-(4-propylphenyl)aniline Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(N)C=C1 UNHOIPHYTXGJQL-UHFFFAOYSA-N 0.000 description 1
- NTGJOYPFNABNES-UHFFFAOYSA-N 4-[(4-amino-2-methylcyclohexyl)methyl]-3-methylcyclohexan-1-amine Chemical compound CC1CC(N)CCC1CC1C(C)CC(N)CC1 NTGJOYPFNABNES-UHFFFAOYSA-N 0.000 description 1
- YFKPQCYLWJULME-UHFFFAOYSA-N 4-[(4-amino-2-methylphenyl)methyl]-3-methylaniline Chemical compound CC1=CC(N)=CC=C1CC1=CC=C(N)C=C1C YFKPQCYLWJULME-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- ZRZCNDIPIZYLSC-UHFFFAOYSA-N 4-[(4-aminophenoxy)methoxy]aniline Chemical compound C1=CC(N)=CC=C1OCOC1=CC=C(N)C=C1 ZRZCNDIPIZYLSC-UHFFFAOYSA-N 0.000 description 1
- BLMSGSGJGUHKFW-UHFFFAOYSA-N 4-[(4-aminophenyl)-diphenylsilyl]aniline Chemical compound C1=CC(N)=CC=C1[Si](C=1C=CC(N)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BLMSGSGJGUHKFW-UHFFFAOYSA-N 0.000 description 1
- FWPQAYDKDSTZHK-UHFFFAOYSA-N 4-[(4-carboxyphenyl)-dimethylsilyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1[Si](C)(C)C1=CC=C(C(O)=O)C=C1 FWPQAYDKDSTZHK-UHFFFAOYSA-N 0.000 description 1
- GAMSSMZJKUMFEY-UHFFFAOYSA-N 4-[(4-carboxyphenyl)disulfanyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1SSC1=CC=C(C(O)=O)C=C1 GAMSSMZJKUMFEY-UHFFFAOYSA-N 0.000 description 1
- HNRMNPACPGIEKD-UHFFFAOYSA-N 4-[(4-ethylphenyl)methyl]aniline Chemical compound C1=CC(CC)=CC=C1CC1=CC=C(N)C=C1 HNRMNPACPGIEKD-UHFFFAOYSA-N 0.000 description 1
- SBBQDUFLZGOASY-OWOJBTEDSA-N 4-[(e)-2-(4-carboxyphenyl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=C(C(O)=O)C=C1 SBBQDUFLZGOASY-OWOJBTEDSA-N 0.000 description 1
- CYZXADZRNSLZKI-UHFFFAOYSA-N 4-[1-(4-aminophenoxy)ethoxy]aniline Chemical compound C=1C=C(N)C=CC=1OC(C)OC1=CC=C(N)C=C1 CYZXADZRNSLZKI-UHFFFAOYSA-N 0.000 description 1
- HSBOCPVKJMBWTF-UHFFFAOYSA-N 4-[1-(4-aminophenyl)ethyl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)C1=CC=C(N)C=C1 HSBOCPVKJMBWTF-UHFFFAOYSA-N 0.000 description 1
- ISESBQNCWCFFFR-UHFFFAOYSA-N 4-[2-(4-amino-2-methylphenyl)ethyl]-3-methylaniline Chemical compound CC1=CC(N)=CC=C1CCC1=CC=C(N)C=C1C ISESBQNCWCFFFR-UHFFFAOYSA-N 0.000 description 1
- ZWERWOZAVGDEAJ-UHFFFAOYSA-N 4-[2-(4-amino-3-methylphenyl)ethyl]-2-methylaniline Chemical compound C1=C(N)C(C)=CC(CCC=2C=C(C)C(N)=CC=2)=C1 ZWERWOZAVGDEAJ-UHFFFAOYSA-N 0.000 description 1
- IYMMZGRJAMFSKQ-UHFFFAOYSA-N 4-[2-(4-aminophenoxy)propan-2-yloxy]aniline Chemical compound C=1C=C(N)C=CC=1OC(C)(C)OC1=CC=C(N)C=C1 IYMMZGRJAMFSKQ-UHFFFAOYSA-N 0.000 description 1
- BEKFRNOZJSYWKZ-UHFFFAOYSA-N 4-[2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C=C1 BEKFRNOZJSYWKZ-UHFFFAOYSA-N 0.000 description 1
- HCUNREWMFYCWAQ-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)ethyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CCC1=CC=C(C(O)=O)C=C1 HCUNREWMFYCWAQ-UHFFFAOYSA-N 0.000 description 1
- ARBAMECCCQZCSR-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)ethynyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C#CC1=CC=C(C(O)=O)C=C1 ARBAMECCCQZCSR-UHFFFAOYSA-N 0.000 description 1
- FDHZNXYLISNHCG-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)phenyl]benzoic acid Chemical compound C1(=CC=C(C=C1)C(=O)O)C=1C(=CC=CC1)C1=CC=C(C=C1)C(=O)O FDHZNXYLISNHCG-UHFFFAOYSA-N 0.000 description 1
- DGUJJOYLOCXENZ-UHFFFAOYSA-N 4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenol Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 DGUJJOYLOCXENZ-UHFFFAOYSA-N 0.000 description 1
- RNCLEMNEEVYSDG-UHFFFAOYSA-N 4-[2-[4-[2-(4-amino-3-methylphenyl)ethyl]phenyl]ethyl]-2-methylaniline Chemical compound C1=C(N)C(C)=CC(CCC=2C=CC(CCC=3C=C(C)C(N)=CC=3)=CC=2)=C1 RNCLEMNEEVYSDG-UHFFFAOYSA-N 0.000 description 1
- RXYQXYDFZDWVIY-UHFFFAOYSA-N 4-[2-[4-[2-(4-aminophenyl)ethyl]phenyl]ethyl]aniline Chemical compound C1=CC(N)=CC=C1CCC(C=C1)=CC=C1CCC1=CC=C(N)C=C1 RXYQXYDFZDWVIY-UHFFFAOYSA-N 0.000 description 1
- ZLUOBULLSMHZDE-UHFFFAOYSA-N 4-[3-(4-amino-2-methylphenyl)propyl]-3-methylaniline Chemical compound CC1=CC(N)=CC=C1CCCC1=CC=C(N)C=C1C ZLUOBULLSMHZDE-UHFFFAOYSA-N 0.000 description 1
- OUSCPPHKIMEIII-UHFFFAOYSA-N 4-[3-(4-amino-3-methylphenyl)propyl]-2-methylaniline Chemical compound C1=C(N)C(C)=CC(CCCC=2C=C(C)C(N)=CC=2)=C1 OUSCPPHKIMEIII-UHFFFAOYSA-N 0.000 description 1
- BMIUMBLWVWZIHD-UHFFFAOYSA-N 4-[3-(4-aminophenyl)propyl]aniline Chemical compound C1=CC(N)=CC=C1CCCC1=CC=C(N)C=C1 BMIUMBLWVWZIHD-UHFFFAOYSA-N 0.000 description 1
- HHLMWQDRYZAENA-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 HHLMWQDRYZAENA-UHFFFAOYSA-N 0.000 description 1
- UXBSLADVESNJEO-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]butan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(CC)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 UXBSLADVESNJEO-UHFFFAOYSA-N 0.000 description 1
- OOUSPOUCRGQLPK-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]cyclohexyl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C2C(CCCC2)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 OOUSPOUCRGQLPK-UHFFFAOYSA-N 0.000 description 1
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 1
- AOOQHLMBCLETRG-UHFFFAOYSA-N 4-[4-[3-[4-(4-aminophenoxy)phenyl]cyclohexyl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C2CC(CCC2)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 AOOQHLMBCLETRG-UHFFFAOYSA-N 0.000 description 1
- BYNNPILRRDIVMP-UHFFFAOYSA-N 4-[4-[3-[4-(4-aminophenoxy)phenyl]phenyl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C=2C=C(C=CC=2)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 BYNNPILRRDIVMP-UHFFFAOYSA-N 0.000 description 1
- MRTAEHMRKDVKMS-UHFFFAOYSA-N 4-[4-[4-(3,4-dicarboxyphenoxy)phenyl]sulfanylphenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC(C=C1)=CC=C1SC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 MRTAEHMRKDVKMS-UHFFFAOYSA-N 0.000 description 1
- SXTPNMJRVQKNRN-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]sulfanylphenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1SC(C=C1)=CC=C1OC1=CC=C(N)C=C1 SXTPNMJRVQKNRN-UHFFFAOYSA-N 0.000 description 1
- UTDAGHZGKXPRQI-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(S(=O)(=O)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 UTDAGHZGKXPRQI-UHFFFAOYSA-N 0.000 description 1
- CHDKLLHFQQJGHN-UHFFFAOYSA-N 4-[4-[4-[4-(4-aminophenoxy)phenyl]cyclohexyl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C2CCC(CC2)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 CHDKLLHFQQJGHN-UHFFFAOYSA-N 0.000 description 1
- QMADXBFHURYUBT-UHFFFAOYSA-N 4-[4-[4-[4-(4-aminophenoxy)phenyl]phenyl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C=2C=CC(=CC=2)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 QMADXBFHURYUBT-UHFFFAOYSA-N 0.000 description 1
- RPSJPQWLOZDXCD-UHFFFAOYSA-N 4-[[4-[(4-amino-3-methylphenyl)methyl]phenyl]methyl]-2-methylaniline Chemical compound C1=C(N)C(C)=CC(CC=2C=CC(CC=3C=C(C)C(N)=CC=3)=CC=2)=C1 RPSJPQWLOZDXCD-UHFFFAOYSA-N 0.000 description 1
- PBPYNPXJEIOCEL-UHFFFAOYSA-N 4-[[4-[(4-aminophenyl)methyl]phenyl]methyl]aniline Chemical compound C1=CC(N)=CC=C1CC(C=C1)=CC=C1CC1=CC=C(N)C=C1 PBPYNPXJEIOCEL-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 1
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 description 1
- GGTGOMFBWCCGLU-UHFFFAOYSA-N 5-azabicyclo[2.2.2]octane-2,8-diamine Chemical compound N1CC2C(N)CC1C(N)C2 GGTGOMFBWCCGLU-UHFFFAOYSA-N 0.000 description 1
- FCGPQGUCEQKMJP-UHFFFAOYSA-N 5-methyl-5-phenylhexan-1-amine Chemical compound NCCCCC(C)(C)C1=CC=CC=C1 FCGPQGUCEQKMJP-UHFFFAOYSA-N 0.000 description 1
- PMZBHPUNQNKBOA-UHFFFAOYSA-N 5-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC(C(O)=O)=CC(C(O)=O)=C1 PMZBHPUNQNKBOA-UHFFFAOYSA-N 0.000 description 1
- AEIDUEAPQMAEDC-UHFFFAOYSA-N 5-oxabicyclo[2.2.2]octane-2,8-diamine Chemical compound O1CC2C(N)CC1C(N)C2 AEIDUEAPQMAEDC-UHFFFAOYSA-N 0.000 description 1
- BJLUCDZIWWSFIB-UHFFFAOYSA-N 5-tert-butylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(O)=O)=C1 BJLUCDZIWWSFIB-UHFFFAOYSA-N 0.000 description 1
- WIAKDOFZRYYUGU-UHFFFAOYSA-N 5-thiabicyclo[2.2.2]octane-2,8-diamine Chemical compound S1CC2C(N)CC1C(N)C2 WIAKDOFZRYYUGU-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- QZHKMYGKCQTOID-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane-2,3-diamine Chemical compound C1CC2C(N)C(N)C1N2 QZHKMYGKCQTOID-UHFFFAOYSA-N 0.000 description 1
- MCVHNWLEOYQHGA-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane-3,5-diamine Chemical compound C1C(N)C2C(N)CC1N2 MCVHNWLEOYQHGA-UHFFFAOYSA-N 0.000 description 1
- PZKJKNURTMDDAM-UHFFFAOYSA-N 7-thiabicyclo[2.2.1]heptane-2,3-diamine Chemical compound C1CC2C(N)C(N)C1S2 PZKJKNURTMDDAM-UHFFFAOYSA-N 0.000 description 1
- BNDPLEYTJPNZFO-UHFFFAOYSA-N 7-thiabicyclo[2.2.1]heptane-2,5-diamine Chemical compound S1C2C(N)CC1C(N)C2 BNDPLEYTJPNZFO-UHFFFAOYSA-N 0.000 description 1
- NHSRVPVZGKKGKC-UHFFFAOYSA-N 7-thiabicyclo[2.2.1]heptane-3,5-diamine Chemical compound C1C(N)C2C(N)CC1S2 NHSRVPVZGKKGKC-UHFFFAOYSA-N 0.000 description 1
- GKILRXCKCZWNEI-UHFFFAOYSA-N 9-azabicyclo[3.2.2]nonane-4,7-diamine Chemical compound N1CC2C(N)CC1C(N)CC2 GKILRXCKCZWNEI-UHFFFAOYSA-N 0.000 description 1
- NBRLWWZQPQDHTQ-UHFFFAOYSA-N 9-oxabicyclo[3.2.2]nonane-4,7-diamine Chemical compound O1CC2C(N)CC1C(N)CC2 NBRLWWZQPQDHTQ-UHFFFAOYSA-N 0.000 description 1
- PGDIJTMOHORACQ-UHFFFAOYSA-N 9-prop-2-enoyloxynonyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCOC(=O)C=C PGDIJTMOHORACQ-UHFFFAOYSA-N 0.000 description 1
- VIBHJVLLDJPBAM-UHFFFAOYSA-N 9-thiabicyclo[3.2.2]nonane-4,7-diamine Chemical compound S1CC2C(N)CC1C(N)CC2 VIBHJVLLDJPBAM-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- DEVXQDKRGJCZMV-UHFFFAOYSA-K Aluminum acetoacetate Chemical compound [Al+3].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O.CC(=O)CC([O-])=O DEVXQDKRGJCZMV-UHFFFAOYSA-K 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- YCPKNBJRCHVGKE-UHFFFAOYSA-N C(=O)(O)C1=CC=C(C=CC(=O)O)C=C1.C1(=CC=C(C=C1)CCC(=O)O)CCC(=O)O Chemical compound C(=O)(O)C1=CC=C(C=CC(=O)O)C=C1.C1(=CC=C(C=C1)CCC(=O)O)CCC(=O)O YCPKNBJRCHVGKE-UHFFFAOYSA-N 0.000 description 1
- LWBIQFKEKJTQAG-UHFFFAOYSA-N C(=O)(O)C=1C=C(OCC(C)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC1C(=O)O Chemical compound C(=O)(O)C=1C=C(OCC(C)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC1C(=O)O LWBIQFKEKJTQAG-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C(*1C)=O)N(C)C1=O Chemical compound CC(C(*1C)=O)N(C)C1=O 0.000 description 1
- HDICIMRANLAWOM-UHFFFAOYSA-N CO.CO.C1CCc2ccccc2C1 Chemical compound CO.CO.C1CCc2ccccc2C1 HDICIMRANLAWOM-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Natural products OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YUTVPRDFNHJKNV-UHFFFAOYSA-N OC(C(C=CC(CC(C1=CC=CC=C1)C1=CC=CC=C1)=C1)=C1C(O)=O)=O Chemical compound OC(C(C=CC(CC(C1=CC=CC=C1)C1=CC=CC=C1)=C1)=C1C(O)=O)=O YUTVPRDFNHJKNV-UHFFFAOYSA-N 0.000 description 1
- JMMSLMMJRMCXPW-UHFFFAOYSA-N OC.OC.C1CC2CCC1C2 Chemical compound OC.OC.C1CC2CCC1C2 JMMSLMMJRMCXPW-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Chemical class 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- DNVYVPFIUACHRK-UHFFFAOYSA-N S1N=C(C(=N1)C(=O)O)C(=O)O.C1(=CC=CC=C1)C=1SC(=C(N1)C(=O)O)C(=O)O Chemical compound S1N=C(C(=N1)C(=O)O)C(=O)O.C1(=CC=CC=C1)C=1SC(=C(N1)C(=O)O)C(=O)O DNVYVPFIUACHRK-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- XLHSVMYMLCFUFU-UHFFFAOYSA-N [1-(hydroxymethyl)cyclododecyl]methanol Chemical compound OCC1(CO)CCCCCCCCCCC1 XLHSVMYMLCFUFU-UHFFFAOYSA-N 0.000 description 1
- KEUCYUPOICDBOG-UHFFFAOYSA-N [2-(aminomethyl)-5-bicyclo[2.2.1]heptanyl]methanamine Chemical compound C1C2C(CN)CC1C(CN)C2 KEUCYUPOICDBOG-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 description 1
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- WYOFTXWVYIGTCT-UHFFFAOYSA-K [OH-].[Sb+3].OCC([O-])=O.OCC([O-])=O Chemical compound [OH-].[Sb+3].OCC([O-])=O.OCC([O-])=O WYOFTXWVYIGTCT-UHFFFAOYSA-K 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- PAVQGHWQOQZQEH-UHFFFAOYSA-N adamantane-1,3-dicarboxylic acid Chemical compound C1C(C2)CC3CC1(C(=O)O)CC2(C(O)=O)C3 PAVQGHWQOQZQEH-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005082 alkoxyalkenyl group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- MJWPFSQVORELDX-UHFFFAOYSA-K aluminium formate Chemical compound [Al+3].[O-]C=O.[O-]C=O.[O-]C=O MJWPFSQVORELDX-UHFFFAOYSA-K 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
- 229940009827 aluminum acetate Drugs 0.000 description 1
- 229940118662 aluminum carbonate Drugs 0.000 description 1
- DMGNPLVEZUUCBT-UHFFFAOYSA-K aluminum;propanoate Chemical compound [Al+3].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O DMGNPLVEZUUCBT-UHFFFAOYSA-K 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- HJGMZNDYNFRASP-UHFFFAOYSA-N anthracene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C=C3C(C(=O)O)=CC=C(C(O)=O)C3=CC2=C1 HJGMZNDYNFRASP-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 229940026189 antimony potassium tartrate Drugs 0.000 description 1
- SZXAQBAUDGBVLT-UHFFFAOYSA-H antimony(3+);2,3-dihydroxybutanedioate Chemical compound [Sb+3].[Sb+3].[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O SZXAQBAUDGBVLT-UHFFFAOYSA-H 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- DVWBKCSKPCZFDE-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-2,3-dicarboxylic acid Chemical compound C1CC2C(C(=O)O)=C(C(O)=O)C1C2 DVWBKCSKPCZFDE-UHFFFAOYSA-N 0.000 description 1
- NOWBCCCXVKRUCT-UHFFFAOYSA-N bicyclo[2.2.1]heptane-2,3,5-tricarboxylic acid Chemical compound C1C2C(C(=O)O)CC1C(C(O)=O)C2C(O)=O NOWBCCCXVKRUCT-UHFFFAOYSA-N 0.000 description 1
- ZPKDUFWKBQYUAT-UHFFFAOYSA-N bicyclo[2.2.1]heptane-2,3-diamine Chemical compound C1CC2C(N)C(N)C1C2 ZPKDUFWKBQYUAT-UHFFFAOYSA-N 0.000 description 1
- KVMMOSKKPJEDNG-UHFFFAOYSA-N bicyclo[2.2.1]heptane-2,5-diamine Chemical compound C1C2C(N)CC1C(N)C2 KVMMOSKKPJEDNG-UHFFFAOYSA-N 0.000 description 1
- VMQNOUCSRQVOKM-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,5-diamine Chemical compound C1C(N)C2C(N)CC1C2 VMQNOUCSRQVOKM-UHFFFAOYSA-N 0.000 description 1
- QRUKTBUQLMMSLJ-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,7-diamine Chemical compound C1CC2C(N)CC1C2N QRUKTBUQLMMSLJ-UHFFFAOYSA-N 0.000 description 1
- WMVVDNYVSPDUOK-UHFFFAOYSA-N bicyclo[2.2.2]oct-5-ene-2,8-diamine Chemical compound C1=CC2C(N)CC1C(N)C2 WMVVDNYVSPDUOK-UHFFFAOYSA-N 0.000 description 1
- KVOACUMJSXEJQT-UHFFFAOYSA-N bicyclo[2.2.2]octane-1,4-dicarboxylic acid Chemical compound C1CC2(C(O)=O)CCC1(C(=O)O)CC2 KVOACUMJSXEJQT-UHFFFAOYSA-N 0.000 description 1
- ATWXWUKNXUEHLH-UHFFFAOYSA-N bicyclo[2.2.2]octane-2,3-diamine Chemical compound C1CC2C(N)C(N)C1CC2 ATWXWUKNXUEHLH-UHFFFAOYSA-N 0.000 description 1
- DOYWWWWTUGGBQS-UHFFFAOYSA-N bicyclo[2.2.2]octane-2,3-dicarboxylic acid Chemical compound C1CC2CCC1C(C(=O)O)C2C(O)=O DOYWWWWTUGGBQS-UHFFFAOYSA-N 0.000 description 1
- YUKKUIVAFGUQHO-UHFFFAOYSA-N bicyclo[2.2.2]octane-2,5-diamine Chemical compound C1CC2C(N)CC1C(N)C2 YUKKUIVAFGUQHO-UHFFFAOYSA-N 0.000 description 1
- JZKBFQDNUYDKPR-UHFFFAOYSA-N bicyclo[2.2.2]octane-3,5-diamine Chemical compound C1CC2C(N)CC1CC2N JZKBFQDNUYDKPR-UHFFFAOYSA-N 0.000 description 1
- RQULFEZQABDREJ-UHFFFAOYSA-N bicyclo[3.2.2]non-8-ene-4,7-diamine Chemical compound C1=CC2C(N)CC1C(N)CC2 RQULFEZQABDREJ-UHFFFAOYSA-N 0.000 description 1
- VTACCVLVFQUQHJ-UHFFFAOYSA-N bicyclo[3.2.2]nonane-4,7-diamine Chemical compound C1CC2C(N)CC1C(N)CC2 VTACCVLVFQUQHJ-UHFFFAOYSA-N 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
- PUPQHRZQMWRAHT-UHFFFAOYSA-N biphenylene-1,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC2=C3C(C(=O)O)=CC=CC3=C21 PUPQHRZQMWRAHT-UHFFFAOYSA-N 0.000 description 1
- ZCLVNIZJEKLGFA-UHFFFAOYSA-H bis(4,5-dioxo-1,3,2-dioxalumolan-2-yl) oxalate Chemical compound [Al+3].[Al+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O ZCLVNIZJEKLGFA-UHFFFAOYSA-H 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 1
- FJTUUPVRIANHEX-UHFFFAOYSA-N butan-1-ol;phosphoric acid Chemical compound CCCCO.OP(O)(O)=O FJTUUPVRIANHEX-UHFFFAOYSA-N 0.000 description 1
- GGHTWSNOKADVAG-UHFFFAOYSA-N butan-1-olate germanium(4+) Chemical compound [Ge+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] GGHTWSNOKADVAG-UHFFFAOYSA-N 0.000 description 1
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- HMPHJJBZKIZRHG-UHFFFAOYSA-N chloromethanesulfonic acid Chemical compound OS(=O)(=O)CCl HMPHJJBZKIZRHG-UHFFFAOYSA-N 0.000 description 1
- MUYSADWCWFFZKR-UHFFFAOYSA-N cinchomeronic acid Chemical compound OC(=O)C1=CC=NC=C1C(O)=O MUYSADWCWFFZKR-UHFFFAOYSA-N 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000011231 conductive filler Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- YHAJXZJGWSOHHZ-UHFFFAOYSA-N cyclobut-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1C=CC1C(O)=O YHAJXZJGWSOHHZ-UHFFFAOYSA-N 0.000 description 1
- CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 description 1
- SUSAGCZZQKACKE-UHFFFAOYSA-N cyclobutane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC1C(O)=O SUSAGCZZQKACKE-UHFFFAOYSA-N 0.000 description 1
- UMOGLHXZZGEOAW-UHFFFAOYSA-N cyclobutene-1,2-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)CC1 UMOGLHXZZGEOAW-UHFFFAOYSA-N 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical compound C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- MNUSMUGFHGAOIW-UHFFFAOYSA-N cyclohexane-1,1,2-tricarboxylic acid Chemical compound OC(=O)C1CCCCC1(C(O)=O)C(O)=O MNUSMUGFHGAOIW-UHFFFAOYSA-N 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- SMEJCQZFRMVYGC-UHFFFAOYSA-N cyclohexane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C(C(O)=O)C1C(O)=O SMEJCQZFRMVYGC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- STZIXLPVKZUAMV-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1(C(O)=O)C(O)=O STZIXLPVKZUAMV-UHFFFAOYSA-N 0.000 description 1
- YZFOGXKZTWZVFN-UHFFFAOYSA-N cyclopentane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1 YZFOGXKZTWZVFN-UHFFFAOYSA-N 0.000 description 1
- ASJCSAKCMTWGAH-UHFFFAOYSA-N cyclopentane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCC1C(O)=O ASJCSAKCMTWGAH-UHFFFAOYSA-N 0.000 description 1
- LNGJOYPCXLOTKL-UHFFFAOYSA-N cyclopentane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C1 LNGJOYPCXLOTKL-UHFFFAOYSA-N 0.000 description 1
- FDKLLWKMYAMLIF-UHFFFAOYSA-N cyclopropane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC1 FDKLLWKMYAMLIF-UHFFFAOYSA-N 0.000 description 1
- RLWFMZKPPHHHCB-UHFFFAOYSA-N cyclopropane-1,2-dicarboxylate;hydron Chemical compound OC(=O)C1CC1C(O)=O RLWFMZKPPHHHCB-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- UCXUKTLCVSGCNR-UHFFFAOYSA-N diethylsilane Chemical compound CC[SiH2]CC UCXUKTLCVSGCNR-UHFFFAOYSA-N 0.000 description 1
- OREAFAJWWJHCOT-UHFFFAOYSA-N dimethylmalonic acid Chemical compound OC(=O)C(C)(C)C(O)=O OREAFAJWWJHCOT-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- MPFLRYZEEAQMLQ-UHFFFAOYSA-N dinicotinic acid Chemical compound OC(=O)C1=CN=CC(C(O)=O)=C1 MPFLRYZEEAQMLQ-UHFFFAOYSA-N 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- WBTCZEPSIIFINA-MSFWTACDSA-J dipotassium;antimony(3+);(2r,3r)-2,3-dioxidobutanedioate;trihydrate Chemical compound O.O.O.[K+].[K+].[Sb+3].[Sb+3].[O-]C(=O)[C@H]([O-])[C@@H]([O-])C([O-])=O.[O-]C(=O)[C@H]([O-])[C@@H]([O-])C([O-])=O WBTCZEPSIIFINA-MSFWTACDSA-J 0.000 description 1
- GKMXREIWPASRMP-UHFFFAOYSA-J dipotassium;oxalate;oxygen(2-);titanium(4+) Chemical compound [O-2].[K+].[K+].[Ti+4].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O GKMXREIWPASRMP-UHFFFAOYSA-J 0.000 description 1
- RRXIMIUKWZOSCG-UHFFFAOYSA-N dodecane-2,3,7,8-tetracarboxylic acid Chemical compound CCCC(C(O)=O)C(C(O)=O)CCCC(C(O)=O)C(CC)C(O)=O RRXIMIUKWZOSCG-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- HFKBPAKZRASAGX-UHFFFAOYSA-N ethane-1,1,1,2-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)(C(O)=O)C(O)=O HFKBPAKZRASAGX-UHFFFAOYSA-N 0.000 description 1
- KXGQYTVFZLIEIF-UHFFFAOYSA-N ethanol;naphthalene Chemical compound CCO.CCO.C1=CC=CC2=CC=CC=C21 KXGQYTVFZLIEIF-UHFFFAOYSA-N 0.000 description 1
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 description 1
- CTCOPPBXAFHGRB-UHFFFAOYSA-N ethanolate;germanium(4+) Chemical compound [Ge+4].CC[O-].CC[O-].CC[O-].CC[O-] CTCOPPBXAFHGRB-UHFFFAOYSA-N 0.000 description 1
- VCYZVXRKYPKDQB-UHFFFAOYSA-N ethyl 2-fluoroacetate Chemical compound CCOC(=O)CF VCYZVXRKYPKDQB-UHFFFAOYSA-N 0.000 description 1
- JLHMVTORNNQCRM-UHFFFAOYSA-N ethylphosphine Chemical compound CCP JLHMVTORNNQCRM-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- SYLAFCZSYRXBJF-UHFFFAOYSA-N furan-3,4-dicarboxylic acid Chemical compound OC(=O)C1=COC=C1C(O)=O SYLAFCZSYRXBJF-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 150000002291 germanium compounds Chemical class 0.000 description 1
- 229940119177 germanium dioxide Drugs 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- MJIVRKPEXXHNJT-UHFFFAOYSA-N lutidinic acid Chemical compound OC(=O)C1=CC=NC(C(O)=O)=C1 MJIVRKPEXXHNJT-UHFFFAOYSA-N 0.000 description 1
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- VAWFFNJAPKXVPH-UHFFFAOYSA-N naphthalene-1,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(C(=O)O)=CC=C21 VAWFFNJAPKXVPH-UHFFFAOYSA-N 0.000 description 1
- GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- UFOIOXZLTXNHQH-UHFFFAOYSA-N oxolane-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1OC(C(O)=O)C(C(O)=O)C1C(O)=O UFOIOXZLTXNHQH-UHFFFAOYSA-N 0.000 description 1
- LIYKJALVRPGQTR-UHFFFAOYSA-M oxostibanylium;chloride Chemical compound [Cl-].[Sb+]=O LIYKJALVRPGQTR-UHFFFAOYSA-M 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- DCKVFVYPWDKYDN-UHFFFAOYSA-L oxygen(2-);titanium(4+);sulfate Chemical compound [O-2].[Ti+4].[O-]S([O-])(=O)=O DCKVFVYPWDKYDN-UHFFFAOYSA-L 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000570 polyether Chemical class 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- KBHBDZQAQRNXRB-UHFFFAOYSA-N propan-2-olate;titanium(3+) Chemical compound [Ti+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] KBHBDZQAQRNXRB-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229940039790 sodium oxalate Drugs 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KQAGKTURZUKUCH-UHFFFAOYSA-L strontium oxalate Chemical compound [Sr+2].[O-]C(=O)C([O-])=O KQAGKTURZUKUCH-UHFFFAOYSA-L 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229940074412 sulfur iodide Drugs 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- OAXARSVKYJPDPA-UHFFFAOYSA-N tert-butyl 4-prop-2-ynylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(CC#C)CC1 OAXARSVKYJPDPA-UHFFFAOYSA-N 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 229910000348 titanium sulfate Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium(IV) ethoxide Substances [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- QWFRRFLKWRIKSZ-UHFFFAOYSA-N truxillic acid Chemical compound OC(=O)C1C(C=2C=CC=CC=2)C(C(O)=O)C1C1=CC=CC=C1 QWFRRFLKWRIKSZ-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/306—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/695—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences
- C08G77/455—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences containing polyamide, polyesteramide or polyimide sequences
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Silicon Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Laminated Bodies (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
[1] 式(1)で示される化合物:
ここに、R1はフェニルであり;Q1は炭素数1〜10のアルキル、シクロペンチル、シクロヘキシル、またはフェニルであり;そして、Q2は式(2)で示される基である:
ここに、記号<はケイ素との結合点を示す;l、m、nおよびpは独立して0、1、2または3であるが、これらの合計は1〜4である;A1、A2、A3およびA4は独立して1,4−シクロヘキシレン、1,4−フェニレン、1,3−ジオキサン−2,5−ジイル、ピリジン−2,5−ジイルまたはピリミジン−2,5−ジイルであり;これらの環における任意の水素はフッ素、塩素または炭素数1〜5のアルキルで置き換えられてもよい;この炭素数1〜5のアルキルにおいて、相隣接しない任意の−CH2−は−O−で置き換えられてもよく、そして任意の水素はフッ素で置き換えられてもよい;Z0、Z1、Z2およびZ3は独立して単結合、−CH=CH−、−C≡C−、−COO−、−OCO−、または炭素原子の数が1〜20であり、そして任意の−CH2−が−O−、−S−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよいアルキレンである;Z4は単結合、−CH=CH−、−C≡C−、−COO−、−OCO−、または炭素原子の数が1〜20であり、そして相隣接しない任意の−CH2−が−O−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよいアルキレンである;そして、Y1は−OH、−COOH、−COCl、−COOCH3、−COOC2H5、−NH2、または下記に示されるジカルボン酸無水物基である:
ここに、G1はQ2に結合するジカルボン酸無水物基から2−オキサ−プロパン−1,3−ジオイル基を除いた残基である。
ここに、R 1 はフェニルであり;Q 1 は炭素数1〜10のアルキル、シクロペンチル、シクロヘキシル、またはフェニルであり;そして、Q3は式(4)で表される基である:
ここに、記号<はケイ素との結合点を示す;l、m、nおよびpは独立して0、1、2または3であるが、これらの合計は1〜4である;A1、A2、A3およびA4は、独立して1,4−シクロヘキシレン、1,4−フェニレン、1,3−ジオキサン−2,5−ジイル、ピリジン−2,5−ジイルまたはピリミジン−2,5−ジイルである;これらの環における任意の水素はフッ素、塩素または炭素数1〜5のアルキルで置き換えられてもよい;この炭素数1〜5のアルキルにおいて、相隣接しない任意の−CH2−は−O−で置き換えられてもよく、そして任意の水素はフッ素で置き換えられてもよい;Z0、Z1、Z2およびZ3は、独立して単結合、−CH=CH−、−C≡C−、−COO−、−OCO−、または炭素原子の数が1〜20であり、そして任意の−CH2−が−O−、−S−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよいアルキレンである;W 1 は単結合、または炭素原子の数が1〜20であり、そして相隣接しない任意の−CH2−が−O−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよいアルキレンである;そして、T 1 は−COO−、−OCO−または下記に示される基のいずれかである:
ここに、G 1 はW 1 に結合するジカルボン酸無水物基から2−オキサ−プロパン−1,3−ジオイル基を除いた残基であり、G 2 はトリカルボン酸類の残基の一部またはテトラカルボン酸類の残基の一部である。なお、これらの基において、左側の遊離基がW 1 と結合する遊離基である。
式(2)で表される基において、記号<はケイ素との結合点を示す。式(2)中のA1、A2、A3およびA4は、独立して1,4−シクロヘキシレン、1,4−フェニレン、1,3−ジオキサン−2,5−ジイル、ピリジン−2,5−ジイルまたはピリミジン−2,5−ジイルである。これらの環において、任意の水素はフッ素、塩素、または炭素数1〜5のアルキルで置き換えられてもよい。そして、この炭素数1〜5のアルキルにおいて、相隣接しない任意の−CH2−は−O−で置き換えられてもよく、そして任意の水素はフッ素で置き換えられてもよい。
ここに、G1はQ2に結合するジカルボン酸無水物基から2−オキサ−プロパン−1,3−ジオイル基を除いた残基である。
この式における記号は、式(2)におけるこれらの記号と同様に定義される基であり、これらの好ましい例も式(2)における場合と同様である。W 1 は単結合または炭素数1〜20のアルキレンである。そして、このアルキレン中の相隣接しない任意の−CH2−は、−O−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよい。W1の好ましい例は、炭素原子の数が1〜20であり、そして相隣接しない任意の−CH2−が−O−、−COO−または−OCO−で置き換えられてもよいアルキレンである。
ここに、G 1 は前記のW 1 に結合するジカルボン酸無水物基から2−オキサ−プロパン−1,3−ジオイル基を除いた残基であり、G 2 はトリカルボン酸類の残基の一部またはテトラカルボン酸類の残基の一部である。なお、これらの基において、左側の遊離基がW 1 と結合する遊離基である。
式(5)において、l、m、nおよびpは独立して0、1、2または3であり、これらの合計は1〜4である。Z6は単結合、−CH=CH−、−C≡C−、−COO−、−OCO−または炭素数1〜18のアルキレンであり、このアルキレンにおいて、任意の−CH2−は−O−、−S−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよい。
ホウ酸誘導体(6)と公知の方法で合成されるハライド(7)とを、炭酸塩水溶液とテトラキス(トリフェニルホスフィン)パラジウムのような触媒の存在下で反応させて化合物(1A)を合成する。この化合物(1A)は、公知の方法で合成される化合物(8)にまずn−ブチルリチウムを反応させ、次いで塩化亜鉛を反応させて、それからジクロロビス(トリフェニルホスフィン)パラジウムのような触媒の存在下で、化合物(7)を反応させることによっても合成される。ホウ酸誘導体(6)は化合物(8)をグリニヤール試薬あるいはリチウム試薬に誘導し、これにトリアルキルホウ酸エステルを反応させることによって製造することができる。
化合物(8)にn−ブチルリチウムを、続いて二酸化炭素を反応させてカルボン酸(9)を得る。カルボン酸(9)と、公知の方法で合成されるフェノール(10)とをDCC(1,3−ジシクロヘキシルカルボジイミド)とDMAP(4−ジメチルアミノピリジン)の存在下で脱水させて、−COO−を有する化合物(1B)を合成する。この方法によって、−OCO−を有する化合物も合成することができる。
化合物(7)をn−ブチルリチウムで処理した後、N,N−ジメチルホルムアミドなどのホルムアミドと反応させてアルデヒド(11)を得る。公知の方法で合成されるホスホニウム塩(12)をカリウムt−ブトキシドのような塩基で処理してリンイリドを発生させ、これをアルデヒド(11)に反応させて化合物(1C)を合成する。反応条件によってはシス体が生成するので、必要に応じて公知の方法によりシス体をトランス体に異性化する。
ホスホニウム塩(12)の代わりにホスホニウム塩(13)を用い、(III)項の方法に従って−(CH2)2−CH=CH−を有する化合物を得る。これを接触水素化して化合物(1E)を合成する。
ジクロロパラジウムとハロゲン化銅との触媒存在下で、化合物(8)に2−メチル−3−ブチン−2−オールを反応させたのち、塩基性条件下で脱保護して化合物(14)を得る。そして、ジクロロパラジウムとハロゲン化銅との触媒存在下、化合物(14)を化合物(7)と反応させて、化合物(1F)を合成する。
化合物(11)を水素化ホウ素ナトリウムなどの還元剤で還元して化合物(15)を得る。これを臭化水素酸などでハロゲン化して化合物(16)を得る。炭酸カリウムなどの存在下で、化合物(16)を化合物(10)と反応させて化合物(1G)を合成する。
ここに、G1は前記のQ2に結合するジカルボン酸無水物基から2−オキサ−プロパン−1,3−ジオイル基を除いた残基である。
<重量平均分子量(Mw)および数平均分子量(Mn)>
島津製作所製の島津LC−9A型ゲル浸透クロマトグラフ(GPC)、および昭和電工製のカラムShodex GF−7M HQ(展開溶媒はDMFあるいはTHF、標準物質は分子量既知のポリスチレン)を用いた。
<鉛筆硬度>
ガラス板上に形成させた重合体薄膜について、JIS規格「JIS−K−5600−5−4 引っかき硬度(鉛筆法)」に準拠し、鉛筆硬度計YOSHIMITSU SEIKIC−221を用いて測定した。
<屈折率>
クロム蒸着したガラス板上に形成させた重合体薄膜について測定した。アッベ屈折計ATAGO DR−M2を使用し、中間液に硫黄ヨウ化メチレン溶液を用い、測定波長589.3nm、25℃において、反射式測定法で測定した。
<光線透過率>
ガラス板上に形成させた重合体薄膜について、マイクロ・カラー・アナライザーTC−1800M(東京電色技術センター製)を用いて測定した。
<表面自由エネルギー>
接触角計CA−A(協和界面化学株式会社製)を使用し、重合体薄膜上に滴下した純水(比抵抗18MΩ・cm)およびエチレングリコールの接触角を、25℃において測定し、算出した。
<熱分解開始温度、5%重量減少温度および10%重量減少温度>
ガラス板上に形成させた重合体薄膜を削り取って試料とした。SEIKO SSC5000 TG/DTA 300を使用し、空気雰囲気中で、10℃/分で30℃から800℃に昇温して重量変化を測定し、得られた変曲点から求めた。
なお、実施例で用いる記号の意味は次の通りである。
Ph:フェニル
Me:メチル
TMS:トリメチルシリル基
HMDS:ヘキサメチルジシラザン
THF:テトラヒドロフラン
NMP:N−メチル−2−ピロリドン
窒素雰囲気下、p−ニトロフェノール(25.0g、0.18mol)のN,N−ジメチルホルムアミド(250ml)溶液に炭酸カリウム(49.7g、0.36mol)を加えて懸濁し、3−ブロモプロペン(21.7g、0.18mol)を滴下した。滴下終了後、室温で5時間撹拌した後、水を加えてジエチルエーテルで抽出した。有機層を水洗した後、無水硫酸マグネシウムで乾燥した。減圧下で溶媒を溜去して得られた残査を、シリカゲルカラムクロマトグラフィー(溶出溶媒:トルエン)で精製した。減圧下でトルエンを溜去した後、エタノールから再結晶してアリル−p−ニトロフェニルエーテル(25.7g)を得た。
窒素雰囲気下、化合物(a)(50.0g、43.3mmol)にトルエン(500ml)を加えて懸濁し、白金−ジビニルシロキサン錯体(3wt%トルエン溶液、25μl)を加えて90℃に加熱した。これにアリル−p−ニトロフェニルエーテル(16.3g、91mmol)を5分かけて滴下し、還流状態で2時間加熱した。放冷後、トルエン(100ml)および水(300ml)を加えて抽出した。有機層を水洗した後、無水硫酸マグネシウムで乾燥した。減圧下でトルエンを溜去して、得られた残査をシリカゲルカラムクロマトグラフィー(溶出溶媒:トルエン)で精製した。減圧下でトルエンを溜去した後、エタノール/酢酸エチルから再結晶して化合物(b)18.7gを得た。
1H−NMR(溶媒:CDCl3):δ(ppm);0.34(s,6H)、0.85−0.88(t,4H)、1.92−1.95(m,4H)、3.85−3.88(t,4H)、6.60−6.63(d,4H)、7.15−7.52(m,40H)、7.94−7.97(d,4H).
29Si−NMR(溶媒:CDCl3):δ(ppm);−17.8(d,2Si)、−78.5(s,4Si)、−79.4(t,4Si).
化合物(b)(10.0g、6.61mmol)、Pd/C(1g)、およびTHF(100ml)の混合物を水素雰囲気下、室温で120時間攪拌した。Pd/Cをろ別後、減圧下でTHFを溜去した。得られた残渣をシリカゲルカラムクロマトグラフィー(溶出溶媒:酢酸エチル)で精製した。減圧下で酢酸エチルを溜去して化合物(1−3−7)6.3gを得た。
1H−NMR(溶媒:CDCl3):δ(ppm);0.31(s,6H)、0.83−0.87(t,4H)、1.82−1.87(m,4H)、3.71−3.74(t,4H)、6.51−6.57(d,8H)、7.14−7.95(m,40H).
29Si−NMR(溶媒:CDCl3):δ(ppm);−17.5(d,2Si)、−78.6(s,4Si)、−79.6(t,4Si).
1H−NMR(溶媒:CDCl3):δ(ppm);0.32(s,6H)、0.70−0.79(t,4H)、1.32−1.42(m,6H)、1.74−1.80(m,2H)、1.89−1.99(m,2H)、2.24−2.37(m,2H)、2.51−2.60(m,2H)、7.15−7.56(m,40H).
29Si−NMR(溶媒:CDCl3):δ(ppm);−18.1(d,2Si)、−78.5(s,4Si)、−79.4― −79.8(t,4Si).
窒素雰囲気下、化合物(c)(11.6g、10mmol)、トリエチルアミン(2.5g、25mmol)、およびTHF(200ml)の混合物に、3−アセトキシプロピルメチルジクロロシラン(5.4g、25mmol)を加えて室温で3時間攪拌した。トルエン(200ml)、および水(100ml)を加えて攪拌し、有機層を水洗した後、無水硫酸マグネシウムで乾燥した。トルエンを減圧溜去して得られた残査をメタノールで洗浄し、エタノール/酢酸エチル(100mL)から再結晶して化合物(d)6.51gを得た。
1H−NMR(溶媒:CDCl3):δ(ppm);0.31(s,6H)、0.72−0.75(t,4H)、1.70−1.74(m,4H)、1.88(s,6H)、3.91−3.94(t,4H)、7.18−7.52(m,40H).
29Si−NMR(溶媒:CDCl3):δ(ppm);−17.8(d,2Si)、−78.4(s,4Si)、−79.3(t,4Si).
窒素雰囲気下、化合物(d)(9.0g、6.85mmol)、およびメタノール(1,500ml)の混合物に濃硫酸(3ml)を加えて、還流状態で3時間加熱した。放冷後、メタノールを減圧溜去して、得られた残査にクロロホルム(200ml)および水(100ml)を加えて攪拌し、有機層を水洗した。無水硫酸マグネシウムで乾燥後、クロロホルムを減圧溜去した。得られた残査をメタノールで洗浄して化合物(1−1−1)5.00gを得た。
1H−NMR(溶媒:CDCl3):δ(ppm);0.31(s,6H)、0.71−0.75(t,4H)、1.60−1.66(m,4H)、3.45−3.48(t,4H)、7.18−7.54(m,40H).
29Si−NMR(溶媒:CDCl3):δ(ppm);−17.4(d,2Si)、−78.5(s,4Si)、−79.5(t,4Si).
窒素雰囲気下、HMDS(88.6g、0.55mol)およびTHF(21.5g)の混合物を80℃に加熱し、4−ペンテン酸(100g、1mol)のトルエン(50g)溶液を滴下した。滴下後、100℃で2時間撹拌し、減圧蒸留して4−ペンテン酸トリメチルシリル(130.2g)を得た。この化合物の沸点は83〜84℃/77.1hPaであった。
窒素雰囲気下、化合物(a)(100.0g、86.7mmol)にトルエン(1,000ml)を加えて懸濁させ、白金−ジビニルシロキサン錯体(3wt%トルエン溶液、50μl)を加えて90℃に加熱した。4−ペンテン酸トリメチルシリル(31.4g、182mmol)を滴下し、還流状態で5時間加熱した。放冷後、減圧下でトルエンを溜去し、粗製の化合物(e)(92.9g)を得た。
粗製の化合物(e)(92.9g、61.8mmol)にメタノール(1,000ml)を加えて懸濁させ、室温で3時間撹拌した。この懸濁物からろ取した固体をメタノール/トルエンに溶解し、活性炭(2.7g)を加えて室温で2時間撹拌した。活性炭をろ別後、減圧下で溶媒を溜去した。残渣をエタノール/酢酸エチルから再結晶して、化合物(1−1−2)75.0gを得た。
1H−NMR(溶媒:CDCl3):δ(ppm);0.28(s,6H)、0.72−0.75(t,4H)、1.40−1.43(m,4H)、1.53−1.56(m,4H)、2.08−2.11(t,4H)、7.18−7.53(m,40H).
29Si−NMR(溶媒:CDCl3):δ(ppm);−17.7(d,2Si)、−78.6(s,4Si)、−79.6(t,4Si).
1H−NMR(溶媒:CDCl3):δ(ppm);0.30(s,6H)、0.73−0.76(t,4H)、1.66−1.72(m,4H)、2.42−2.44(m,2H)、2.64−2.66(m,2H)、2.95−2.98(m,2H)、3.15−3.19(m,2H)、3.28−3.39(m,4H)、3.44−3.48(m,2H)、7.18−7.53(m,40H).
29Si−NMR(溶媒:CDCl3):δ(ppm);−17.4(s,2Si)、−78.6(s,4Si)、−79.5― ―79.6(t,4Si).
1H−NMR(溶媒:CDCl3):δ(ppm);0.27(s,6H)、0.60−0.73(m,5H)、0.84−0.92(m,1H)、0.97−1.07(m,2H)、1.62−1.68(m,1H)、1.76−1.84(m,2H)、1.94−1.98(m,2H)、2.90−3.00(m,4H)、7.13−7.54(m,40H).
29Si−NMR(溶媒:CDCl3):δ(ppm);−17.0― ―17.1(d,2Si)、−78.7(s,4Si)、−79.6(s,4Si).
(これらのうち、Q 2 −83−1、Q 2 −83−2、Q 2 −84−1、Q 2 −84−2、Q 2 −85−1、Q 2 −85−2、Q 2 −87−1、Q 2 −87−2、Q 2 −88−1、Q 2 −88−2、Q 2 −89−1およびQ 2 −89−2は参考例である。)
<ポリアミド酸の製造1>
窒素雰囲気下で、4,4’−ジアミノジフェニルエーテル(2.39g)のNMP(45g)溶液を冷却した。反応系の温度を5〜70℃の範囲内に保ちながら、この溶液にピロメリット酸二無水物(2.61g)を添加した。次いで20時間撹拌して、重合体濃度が10重量%であるポリアミド酸ワニス(50g)を得た。このワニスに含まれるポリアミド酸の名称をPA酸1とする。
<ポリアミド酸の製造2>
ピロメリット酸二無水物を化合物(1−1−4)(1.49g)に替え、4,4’−ジアミノジフェニルエーテルを化合物(1−3−7)(1.51g)に替え、そしてNMPの使用量を12gにした以外は比較例1と同様にして、重合体濃度が20重量%であるポリアミド酸ワニス(15g)を得た。このワニスに含まれるポリアミド酸の名称をPA酸2とする。
<ポリアミド酸の製造3>
化合物(1−1−4)をピロメリット酸二無水物(0.39g)に替え、化合物(1−3−7)の使用量を2.61gにした以外は実施例5と同様にして、重合体濃度が20重量%であるポリアミド酸ワニス(15g)を得た。このワニスに含まれるポリアミド酸の名称をPA酸3とする。
<ポリアミド酸の製造4>
化合物(1−1−4)の使用量を2.63gに替え、化合物(1−3−7)を4,4’−ジアミノジフェニルエーテル(0.38g)に替え、そしてNMPの使用量を7gに変えた以外は実施例5と同様にして、重合体濃度が30重量%であるポリアミド酸ワニス(10g)を得た。このワニスに含まれるポリアミド酸の名称をPA酸4とする。
PA酸1〜PA酸4のそれぞれのワニスをブチルセロソルブで適当な濃度に希釈し、ガラス基板上にスピンナーにて塗布した。80℃にて約5分間予備焼成し、それから220℃にて30分間、次いで300℃にて60分間加熱処理を行って、それぞれのポリイミド薄膜を形成させた。これらのポリイミド薄膜をPI−1、PI−2、PI−3およびPI−4とする。PI−1〜PI−4について物性を測定した結果を表29に示す。
<ポリエステルの製造>
窒素雰囲気下で、化合物(1−1−2)(3.12g、2.25mmol)および1,4−ブタンジオール(0.40g、4.44mmol)の混合物にチタントリイソプロポキシド2滴を加え、220℃で1時間加熱撹拌した。冷却後、内容物を取り出し、ポリエステル1.91gを得た。
実施例11で得られたポリエステルの一部をNMP(9g)に完全に溶解させ、この溶液をブチルセルソルブで適当な濃度に希釈して、ガラス基板上にスピンナーを用いて塗布した。80℃にて5分間予備乾燥した後、100℃で1時間、220℃で3時間加熱処理を行い、ポリエステル薄膜PE−1を得た。PE−1について物性を測定した結果を表29に示す。
Claims (18)
- 式(1)で示される化合物:
ここに、R1はフェニルであり;Q1は炭素数1〜10のアルキル、シクロペンチル、シクロヘキシル、またはフェニルであり;そして、Q2は式(2)で示される基である:
ここに、記号<はケイ素との結合点を示す;l、m、nおよびpは独立して0、1、2または3であるが、これらの合計は1〜4である;A1、A2、A3およびA4は独立して1,4−シクロヘキシレン、1,4−フェニレン、1,3−ジオキサン−2,5−ジイル、ピリジン−2,5−ジイルまたはピリミジン−2,5−ジイルであり;これらの環における任意の水素はフッ素、塩素または炭素数1〜5のアルキルで置き換えられてもよい;この炭素数1〜5のアルキルにおいて、相隣接しない任意の−CH2−は−O−で置き換えられてもよく、そして任意の水素はフッ素で置き換えられてもよい;Z0、Z1、Z2およびZ3は独立して単結合、−CH=CH−、−C≡C−、−COO−、−OCO−、または炭素原子の数が1〜20であり、そして任意の−CH2−が−O−、−S−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよいアルキレンである;Z4は単結合、−CH=CH−、−C≡C−、−COO−、−OCO−、または炭素原子の数が1〜20であり、そして相隣接しない任意の−CH2−が−O−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよいアルキレンである;そして、Y1は−OH、−COOH、−COCl、−COOCH3、−COOC2H5、−NH2、または下記に示されるジカルボン酸無水物基である:
ここに、G1はQ2に結合するジカルボン酸無水物基から2−オキサ−プロパン−1,3−ジオイル基を除いた残基である。
- Q1がメチルまたはフェニルである、請求項1に記載の化合物。
- Q1がメチルまたはフェニルであり;A1、A2、A3およびA4が独立して単結合または1,4−フェニレンであり;そして、Z0、Z1、Z2、Z3およびZ4が独立して単結合、−COO−、−OCO−、または炭素原子の数が1〜20であり、そして相隣接しない任意の−CH2−が−O−、−COO−もしくは−OCO−で置き換えられてもよいアルキレンである、請求項1に記載の化合物。
- 式(3)で示される構成単位を有する重合体:
ここに、R 1 はフェニルであり;Q 1 は炭素数1〜10のアルキル、シクロペンチル、シクロヘキシル、またはフェニルであり;そして、Q3は式(4)で表される基である:
ここに、記号<はケイ素との結合点を示す;l、m、nおよびpは独立して0、1、2または3であるが、これらの合計は1〜4である;A1、A2、A3およびA4は、独立して1,4−シクロヘキシレン、1,4−フェニレン、1,3−ジオキサン−2,5−ジイル、ピリジン−2,5−ジイルまたはピリミジン−2,5−ジイルである;これらの環における任意の水素はフッ素、塩素または炭素数1〜5のアルキルで置き換えられてもよい;この炭素数1〜5のアルキルにおいて、相隣接しない任意の−CH2−は−O−で置き換えられてもよく、そして任意の水素はフッ素で置き換えられてもよい;Z0、Z1、Z2およびZ3は、独立して単結合、−CH=CH−、−C≡C−、−COO−、−OCO−、または炭素原子の数が1〜20であり、そして任意の−CH2−が−O−、−S−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよいアルキレンである;W 1 は単結合、または炭素原子の数が1〜20であり、そして相隣接しない任意の−CH2−が−O−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよいアルキレンである;そして、T 1 は−COO−、−OCO−または下記に示される基のいずれかである:
ここに、G 1 はW 1 に結合するジカルボン酸無水物基から2−オキサ−プロパン−1,3−ジオイル基を除いた残基であり、G 2 はトリカルボン酸類の残基の一部またはテトラカルボン酸類の残基の一部である。なお、これらの基において、左側の遊離基がW 1 と結合する遊離基である。 - Q1がメチルまたはフェニルである、請求項4に記載の重合体。
- Q1がメチルまたはフェニルであり;A1、A2、A3およびA 4 が1,4−フェニレンであり;Z0、Z1、Z2およびZ3が、独立して単結合、−COO−、−OCO−、または炭素原子の数が1〜20であり、そして相隣接しない任意の−CH2−が−O−、−COO−または−OCO−で置き換えられてもよいアルキレンである、請求項4に記載の重合体。
- 請求項1に記載の化合物を含有する組成物。
- 請求項1に記載の化合物の少なくとも1つを用いて得られる重合体。
- 請求項1に記載の化合物のみを用いて得られる、請求項8に記載の重合体。
- 重合体がポリイミド、ポリアミド酸、またはポリエステルである、請求項8に記載の重合体。
- 請求項8に記載の重合体の少なくとも1つを含有する組成物。
- 請求項8に記載の重合体の少なくとも1つを含有するコーティング剤。
- 請求項8に記載の重合体の少なくとも1つを含有するワニス組成物。
- 請求項13に記載のワニス組成物を用いて形成される薄膜。
- 請求項13に記載のワニス組成物と他の重合体の組成物の少なくとも1つとを用いて形成される多層薄膜。
- 請求項8に記載の重合体の少なくとも1つが構成要素の一部であるかまたは全てである構造体。
- 請求項14に記載の薄膜を有するプラスチック基板。
- 請求項14に記載の薄膜を有する光学材料。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004053219A JP4483344B2 (ja) | 2003-03-13 | 2004-02-27 | シルセスキオキサン骨格を有する化合物およびその重合体 |
US10/798,872 US20050009982A1 (en) | 2003-03-13 | 2004-03-12 | Compound having silsesquioxane skeleton and its polymer |
US11/704,253 US7705105B2 (en) | 2003-03-13 | 2007-02-09 | Compound having silsequioxane skeleton and its polymer |
US12/659,478 US8236917B2 (en) | 2003-03-13 | 2010-03-10 | Compound having silsesquioxane skeleton and its polymer |
US13/423,548 US8420764B2 (en) | 2003-03-13 | 2012-03-19 | Compound having silsesquioxane skeleton and its polymer |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003067768 | 2003-03-13 | ||
JP2003114221 | 2003-04-18 | ||
JP2004053219A JP4483344B2 (ja) | 2003-03-13 | 2004-02-27 | シルセスキオキサン骨格を有する化合物およびその重合体 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2004331647A JP2004331647A (ja) | 2004-11-25 |
JP4483344B2 true JP4483344B2 (ja) | 2010-06-16 |
Family
ID=33514532
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004053219A Expired - Lifetime JP4483344B2 (ja) | 2003-03-13 | 2004-02-27 | シルセスキオキサン骨格を有する化合物およびその重合体 |
Country Status (2)
Country | Link |
---|---|
US (4) | US20050009982A1 (ja) |
JP (1) | JP4483344B2 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017150589A1 (ja) | 2016-03-02 | 2017-09-08 | Jnc株式会社 | 放熱部材用組成物、放熱部材、電子機器、放熱部材の製造方法 |
Families Citing this family (64)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4306317B2 (ja) * | 2003-04-24 | 2009-07-29 | チッソ株式会社 | 液晶配向膜形成用ワニス、液晶配向膜および液晶表示素子 |
JP4396139B2 (ja) * | 2003-05-27 | 2010-01-13 | チッソ株式会社 | シルセスキオキサン骨格を有するポリマーおよびその薄膜の形成方法 |
JP4963781B2 (ja) * | 2004-02-25 | 2012-06-27 | リンテック株式会社 | ポリシルセスキオキサングラフト共重合体の製造方法、粘着剤および粘着シート |
JP4742216B2 (ja) * | 2004-07-08 | 2011-08-10 | Jnc株式会社 | ケイ素化合物 |
JP2008512546A (ja) * | 2004-09-10 | 2008-04-24 | ダウ・コーニング・コーポレイション | 無水物官能性シルセスキオキサン樹脂 |
EP1686133B1 (en) * | 2004-12-28 | 2008-08-20 | Chisso Corporation | Organosilicon compound |
KR20060095506A (ko) * | 2005-02-28 | 2006-08-31 | 칫소가부시키가이샤 | 케이지형 규소 골격을 가진 유기 규소 화합물 및 고분자화합물 |
JP5082258B2 (ja) * | 2005-02-28 | 2012-11-28 | Jnc株式会社 | カゴ型ケイ素骨格を有する有機ケイ素化合物及び高分子化合物 |
TWI377234B (en) | 2005-02-28 | 2012-11-21 | Jnc Corp | Varnish for forming liquid crystal alignment layer and liquid crystal display element using the same |
JP4682644B2 (ja) * | 2005-02-28 | 2011-05-11 | チッソ株式会社 | シリコーン樹脂成型体用ワニス及びシリコーン樹脂成型体 |
JP4775033B2 (ja) * | 2005-02-28 | 2011-09-21 | Jnc株式会社 | 液晶配向膜形成用ワニス及びそれを用いた液晶表示素子 |
JP4450214B2 (ja) * | 2005-03-11 | 2010-04-14 | セイコーエプソン株式会社 | 有機薄膜トランジスタ、電子デバイスおよび電子機器 |
WO2006102518A1 (en) | 2005-03-24 | 2006-09-28 | Bridgestone Corporation | Compounding silica-reinforced rubber with low volatile organic compound (voc) emission |
US7659050B2 (en) * | 2005-06-07 | 2010-02-09 | International Business Machines Corporation | High resolution silicon-containing resist |
JP4929687B2 (ja) * | 2005-11-16 | 2012-05-09 | Jnc株式会社 | 感光性化合物、添加用化合物、これらを含有するポジ型感光性組成物、及びこのポジ型感光性組成物の膜を有する表示素子 |
US20080221263A1 (en) * | 2006-08-31 | 2008-09-11 | Subbareddy Kanagasabapathy | Coating compositions for producing transparent super-hydrophobic surfaces |
JP2007326988A (ja) * | 2006-06-09 | 2007-12-20 | Chisso Corp | エポキシ樹脂組成物 |
JP5408597B2 (ja) * | 2006-06-13 | 2014-02-05 | 学校法人 関西大学 | 熱硬化性重合体組成物およびその硬化物 |
JP2008106165A (ja) * | 2006-10-26 | 2008-05-08 | Chisso Corp | インクジェット用インクおよび当該インクにより得られる硬化膜 |
US8080604B2 (en) * | 2007-03-02 | 2011-12-20 | Lintec Corporation | Adhesive containing ladder-type polysilsesquioxane and adhesive sheet |
US7915368B2 (en) * | 2007-05-23 | 2011-03-29 | Bridgestone Corporation | Method for making alkoxy-modified silsesquioxanes |
US8501895B2 (en) * | 2007-05-23 | 2013-08-06 | Bridgestone Corporation | Method for making alkoxy-modified silsesquioxanes and amino alkoxy-modified silsesquioxanes |
JP5013127B2 (ja) * | 2007-12-19 | 2012-08-29 | Jnc株式会社 | 熱硬化性樹脂組成物およびその用途 |
US20090163652A1 (en) * | 2007-12-19 | 2009-06-25 | Chisso Corporation | Thermosetting resin composition and use thereof |
US8962746B2 (en) | 2007-12-27 | 2015-02-24 | Bridgestone Corporation | Methods of making blocked-mercapto alkoxy-modified silsesquioxane compounds |
US8794282B2 (en) * | 2007-12-31 | 2014-08-05 | Bridgestone Corporation | Amino alkoxy-modified silsesquioxane adhesives for improved metal adhesion and metal adhesion retention to cured rubber |
US8513371B2 (en) | 2007-12-31 | 2013-08-20 | Bridgestone Corporation | Amino alkoxy-modified silsesquioxanes and method of preparation |
US8633292B2 (en) * | 2009-03-26 | 2014-01-21 | Signet Armorlite | Polyurethane-based photochromic optical materials |
JP5707607B2 (ja) | 2009-04-24 | 2015-04-30 | Jnc株式会社 | 有機ケイ素化合物及びそれを含む熱硬化性樹脂組成物 |
JP5793824B2 (ja) | 2009-06-02 | 2015-10-14 | Jnc株式会社 | 有機ケイ素化合物、該有機ケイ素化合物を含む熱硬化性組成物、および光半導体用封止材料 |
JP5773585B2 (ja) * | 2009-06-29 | 2015-09-02 | 日東電工株式会社 | 発光性トリアリール |
US8182646B2 (en) | 2009-09-30 | 2012-05-22 | Federal-Mogul Corporation | Substrate and rubber composition and method of making the composition |
US8642691B2 (en) | 2009-12-28 | 2014-02-04 | Bridgestone Corporation | Amino alkoxy-modified silsesquioxane adhesives for improved metal adhesion and metal adhesion retention to cured rubber |
EP2573129B1 (en) | 2010-05-18 | 2016-08-17 | JNC Corporation | Novel organosilicon compound and thermosetting resin composition, cured resin, and semiconductor sealing material containing said organosilicon compound |
US8981140B1 (en) * | 2010-08-18 | 2015-03-17 | The United States Of America As Represented By The Secretary Of The Air Force | Peripherally aromatic silsesquioxanes featuring reactive functionality: synthesis and applications thereof |
JP5857039B2 (ja) * | 2011-03-30 | 2016-02-10 | 旭化成ケミカルズ株式会社 | オルガノポリシロキサン、その製造方法、及びオルガノポリシロキサンを含有する硬化性樹脂組成物 |
EP2692776B1 (en) * | 2011-03-30 | 2017-02-22 | Asahi Kasei Kabushiki Kaisha | Organopolysiloxane, method for producing same, and curable resin composition containing organopolysiloxane |
CN103636000B (zh) | 2011-05-12 | 2017-11-17 | 德普伊辛迪斯制品公司 | 具有使公差被最优化的互连的图像传感器 |
JP5387638B2 (ja) * | 2011-09-12 | 2014-01-15 | Jnc株式会社 | エポキシ樹脂組成物 |
US9249313B2 (en) | 2011-09-21 | 2016-02-02 | The United States Of America As Represented By The Secretary Of The Air Force | Synthesis of functional fluorinated polyhedral oligomeric silsesquioxane (F-POSS) |
US9012673B1 (en) | 2011-09-21 | 2015-04-21 | The United States Of America As Represented By The Secretary Of The Air Force | Synthesis and applications of peripherally asymmetric aryl POSS compounds |
BR112015001555A2 (pt) | 2012-07-26 | 2017-07-04 | Olive Medical Corp | vídeo contínuo em ambiente com deficiência de luz |
WO2014018951A1 (en) | 2012-07-26 | 2014-01-30 | Olive Medical Corporation | Ycbcr pulsed illumination scheme in a light deficient environment |
IN2015MN00019A (ja) | 2012-07-26 | 2015-10-16 | Olive Medical Corp | |
US9217064B2 (en) | 2013-01-24 | 2015-12-22 | The United States Of America, As Represented By The Secretary Of The Air Force | Thermosetting resins with enhanced cure characteristics containing organofunctional silane moieties |
DE102013003329A1 (de) * | 2013-02-25 | 2014-08-28 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Silane, Hybridpolymere und Photolack mit Positiv-Resist Verhalten sowie Verfahren zur Herstellung |
EP2967286B1 (en) | 2013-03-15 | 2021-06-23 | DePuy Synthes Products, Inc. | Minimize image sensor i/o and conductor counts in endoscope applications |
EP3459431A1 (en) | 2013-03-15 | 2019-03-27 | DePuy Synthes Products, Inc. | Controlling the integral light energy of a laser pulse |
EP2967294B1 (en) | 2013-03-15 | 2020-07-29 | DePuy Synthes Products, Inc. | Super resolution and color motion artifact correction in a pulsed color imaging system |
AU2014233190B2 (en) | 2013-03-15 | 2018-11-01 | DePuy Synthes Products, Inc. | Image sensor synchronization without input clock and data transmission clock |
US10251530B2 (en) | 2013-03-15 | 2019-04-09 | DePuy Synthes Products, Inc. | Scope sensing in a light controlled environment |
CN103204872A (zh) * | 2013-04-14 | 2013-07-17 | 吉林大学 | 一种二羟基笼形倍半硅氧烷单体及其制备方法 |
US9394408B2 (en) | 2013-08-29 | 2016-07-19 | The United States Of America As Represented By The Secretary Of The Air Force | Controlled polymerization of functional fluorinated polyhedral oligomeric silsesquioxane monomers |
PL228312B1 (pl) | 2014-03-10 | 2018-03-30 | Univ Im Adama Mickiewicza W Poznaniu | Nowe funkcjonalizowane nienasycone pochodne dwuwinylosilseskwioksanów typu double-decker oraz sposób ich otrzymywania |
CN106102559A (zh) | 2014-03-21 | 2016-11-09 | 德普伊新特斯产品公司 | 用于成像传感器的卡缘连接器 |
DE102014212698A1 (de) | 2014-07-01 | 2016-01-07 | Wacker Chemie Ag | Verfahren zur Herstellung von Siloxanen aus Alkalisalzen von Silanolen |
CN104447850A (zh) * | 2014-11-04 | 2015-03-25 | 烟台大学 | 一种双夹板型二乙烯基低聚倍半硅氧烷的制备方法 |
CN114016318A (zh) | 2014-12-31 | 2022-02-08 | 株式会社普利司通 | 用于将钢合金粘附到橡胶的氨基烷氧基改性倍半硅氧烷粘合剂 |
CN104804033A (zh) * | 2015-03-30 | 2015-07-29 | 兰州大学 | 二氟代基poss单体、由其衍生的聚合物及其制备方法 |
CN106279246B (zh) * | 2015-05-21 | 2018-12-18 | 北京化工大学 | 呋喃官能化双塔型多面体低聚倍半硅氧烷及其制备方法 |
CN106279247B (zh) * | 2015-05-21 | 2019-02-26 | 北京化工大学 | 一种呋喃官能化笼型多面体低聚倍半硅氧烷及其制备方法 |
CN110191889A (zh) * | 2017-01-10 | 2019-08-30 | 捷恩智株式会社 | 具有自由基聚合性官能团的倍半硅氧烷衍生物、其组合物以及低固化收缩性固化膜 |
TW202319443A (zh) | 2021-06-29 | 2023-05-16 | 日商東洋紡股份有限公司 | 聚醯胺酸、聚醯亞胺、及其用途 |
WO2023218889A1 (ja) * | 2022-05-13 | 2023-11-16 | Agc株式会社 | 組成物、化合物、表面処理剤、物品、及び物品の製造方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6770724B1 (en) * | 1998-03-03 | 2004-08-03 | The United States Of America As Represented By The Secretary Of The Air Force | Altering of poss rings |
US6927270B2 (en) * | 2001-06-27 | 2005-08-09 | Hybrid Plastics Llp | Process for the functionalization of polyhedral oligomeric silsesquioxanes |
US6767930B1 (en) * | 2001-09-07 | 2004-07-27 | Steven A. Svejda | Polyhedral oligomeric silsesquioxane polyimide composites |
WO2003024870A1 (fr) * | 2001-09-18 | 2003-03-27 | Chisso Corporation | Derives silsesquioxane et procede de fabrication |
JP4381636B2 (ja) * | 2001-11-05 | 2009-12-09 | 新日鐵化学株式会社 | シリコーン樹脂組成物及びシリコーン樹脂成形体 |
JP4259148B2 (ja) * | 2002-03-28 | 2009-04-30 | チッソ株式会社 | 液晶表示パネル用シール材料 |
JP4479160B2 (ja) * | 2003-03-11 | 2010-06-09 | チッソ株式会社 | シルセスキオキサン誘導体を用いて得られる重合体 |
TWI278473B (en) * | 2003-03-12 | 2007-04-11 | Chisso Corp | Polymer with the silsesquioxane skeleton in its main chain, method of forming the same, and coating film and membrane of preventing metal ion elution |
-
2004
- 2004-02-27 JP JP2004053219A patent/JP4483344B2/ja not_active Expired - Lifetime
- 2004-03-12 US US10/798,872 patent/US20050009982A1/en not_active Abandoned
-
2007
- 2007-02-09 US US11/704,253 patent/US7705105B2/en active Active
-
2010
- 2010-03-10 US US12/659,478 patent/US8236917B2/en not_active Expired - Fee Related
-
2012
- 2012-03-19 US US13/423,548 patent/US8420764B2/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017150589A1 (ja) | 2016-03-02 | 2017-09-08 | Jnc株式会社 | 放熱部材用組成物、放熱部材、電子機器、放熱部材の製造方法 |
US10752755B2 (en) | 2016-03-02 | 2020-08-25 | Jnc Corporation | Composition for heat-dissipating member, heat-dissipating member, electronic instrument, and method for producing heat-dissipating member |
Also Published As
Publication number | Publication date |
---|---|
US8420764B2 (en) | 2013-04-16 |
US20050009982A1 (en) | 2005-01-13 |
US8236917B2 (en) | 2012-08-07 |
JP2004331647A (ja) | 2004-11-25 |
US20120178894A1 (en) | 2012-07-12 |
US20100240855A1 (en) | 2010-09-23 |
US20070190344A1 (en) | 2007-08-16 |
US7705105B2 (en) | 2010-04-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4483344B2 (ja) | シルセスキオキサン骨格を有する化合物およびその重合体 | |
JP5978288B2 (ja) | ポリイミド前駆体、ポリイミド、ポリイミドフィルム、ワニス、及び基板 | |
KR101248532B1 (ko) | 액정 배향막 형성용 니스 및 그것을 사용한 액정 표시소자 | |
JP2018066017A (ja) | ポリイミド前駆体及びポリイミド | |
JP5320668B2 (ja) | テトラカルボン酸系化合物及びそのポリイミド、ならびにその製造方法 | |
JP5082258B2 (ja) | カゴ型ケイ素骨格を有する有機ケイ素化合物及び高分子化合物 | |
CN104629663B (zh) | 聚酯热熔胶 | |
KR20060095506A (ko) | 케이지형 규소 골격을 가진 유기 규소 화합물 및 고분자화합물 | |
JP2016074915A (ja) | ポリイミド前駆体、ポリイミド、ポリイミドフィルム、ワニス、及び基板 | |
JP4682644B2 (ja) | シリコーン樹脂成型体用ワニス及びシリコーン樹脂成型体 | |
JP2006233155A (ja) | 平坦化膜用塗布液および平坦化膜 | |
JP7291199B2 (ja) | ハードコート層形成用組成物、及びハードコートフィルム | |
JP6049148B2 (ja) | (ホスホニル)芳香族ジエステルおよび酸のホモポリマーおよびコポリマーの調製 | |
KR20190017749A (ko) | 상이한 2종류의 구조 단위를 갖는 방향족 폴리케톤 | |
JP2015506914A (ja) | (ホスホニル)芳香族ジエステルおよび酸の調製 | |
JP4775033B2 (ja) | 液晶配向膜形成用ワニス及びそれを用いた液晶表示素子 | |
JP2507735B2 (ja) | サ−モトロピツク液晶性コポリエステルの製造法 | |
JP2547820B2 (ja) | 芳香族コポリエステル | |
JPH0826134B2 (ja) | サ−モトロピツク液晶性コポリエステル | |
JPS63186760A (ja) | 芳香族コポリエステル組成物 | |
JPH02166117A (ja) | 芳香族コポリエステル | |
JPH1135665A (ja) | 新規なポリエステル及びその製造方法 | |
JP2022172875A (ja) | ジオール化合物ならびにその製造方法およびその重合体 | |
JPS63277233A (ja) | 芳香族コポリエステル | |
JP2013173869A (ja) | 難燃性ポリエステル組成物およびその製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20061025 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20091006 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20091007 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20091127 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20091222 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100209 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20100302 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100315 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4483344 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130402 Year of fee payment: 3 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313117 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130402 Year of fee payment: 3 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130402 Year of fee payment: 3 |
|
S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130402 Year of fee payment: 3 |
|
R360 | Written notification for declining of transfer of rights |
Free format text: JAPANESE INTERMEDIATE CODE: R360 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130402 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130402 Year of fee payment: 3 |
|
R370 | Written measure of declining of transfer procedure |
Free format text: JAPANESE INTERMEDIATE CODE: R370 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130402 Year of fee payment: 3 |
|
S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130402 Year of fee payment: 3 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130402 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140402 Year of fee payment: 4 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
EXPY | Cancellation because of completion of term |