JP6703025B2 - リン化合物を含むポリウレタンフォーム - Google Patents
リン化合物を含むポリウレタンフォーム Download PDFInfo
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- JP6703025B2 JP6703025B2 JP2018037423A JP2018037423A JP6703025B2 JP 6703025 B2 JP6703025 B2 JP 6703025B2 JP 2018037423 A JP2018037423 A JP 2018037423A JP 2018037423 A JP2018037423 A JP 2018037423A JP 6703025 B2 JP6703025 B2 JP 6703025B2
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- Prior art keywords
- polyurethane foam
- catalyst
- group
- moiety
- foam according
- Prior art date
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- 229920005830 Polyurethane Foam Polymers 0.000 title claims description 46
- 239000011496 polyurethane foam Substances 0.000 title claims description 46
- 150000003018 phosphorus compounds Chemical class 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims description 59
- -1 alkali metal cation Chemical class 0.000 claims description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 239000012948 isocyanate Substances 0.000 claims description 20
- 150000002513 isocyanates Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 17
- 229910019142 PO4 Inorganic materials 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 15
- 229920001228 polyisocyanate Polymers 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 229920000388 Polyphosphate Polymers 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 239000001205 polyphosphate Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 239000004970 Chain extender Substances 0.000 claims description 13
- 235000011176 polyphosphates Nutrition 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 239000004604 Blowing Agent Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 239000010452 phosphate Substances 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 6
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 6
- ZGHUDSLVQAGWEY-UHFFFAOYSA-N [2-[bis(2-chloroethoxy)phosphoryloxymethyl]-3-chloro-2-(chloromethyl)propyl] bis(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCC(CCl)(CCl)COP(=O)(OCCCl)OCCCl ZGHUDSLVQAGWEY-UHFFFAOYSA-N 0.000 claims description 5
- 239000003431 cross linking reagent Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 125000001302 tertiary amino group Chemical group 0.000 claims description 5
- 239000012752 auxiliary agent Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 239000004615 ingredient Substances 0.000 claims 3
- 125000002524 organometallic group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 description 27
- 229920005862 polyol Polymers 0.000 description 26
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 229920002635 polyurethane Polymers 0.000 description 23
- 239000004814 polyurethane Substances 0.000 description 23
- 235000021317 phosphate Nutrition 0.000 description 15
- 230000032683 aging Effects 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 11
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 239000004971 Cross linker Substances 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 239000004114 Ammonium polyphosphate Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 230000003679 aging effect Effects 0.000 description 3
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 3
- 229920001276 ammonium polyphosphate Polymers 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 150000002605 large molecules Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 150000004072 triols Chemical class 0.000 description 3
- KVMPUXDNESXNOH-UHFFFAOYSA-N tris(1-chloropropan-2-yl) phosphate Chemical compound ClCC(C)OP(=O)(OC(C)CCl)OC(C)CCl KVMPUXDNESXNOH-UHFFFAOYSA-N 0.000 description 3
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- NCUPDIHWMQEDPR-UHFFFAOYSA-N 2-[2-[2-(dimethylamino)ethoxy]ethyl-methylamino]ethanol Chemical compound CN(C)CCOCCN(C)CCO NCUPDIHWMQEDPR-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- 239000004721 Polyphenylene oxide Substances 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
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 229910052797 bismuth Inorganic materials 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
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000002666 chemical blowing agent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 125000005842 heteroatom Chemical group 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
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- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- ZFDWWDZLRKHULH-UHFFFAOYSA-N 1,2-dimethyl-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1C ZFDWWDZLRKHULH-UHFFFAOYSA-N 0.000 description 1
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- JGVZJRHAZOBPMW-UHFFFAOYSA-N 1,3-bis(dimethylamino)propan-2-ol Chemical compound CN(C)CC(O)CN(C)C JGVZJRHAZOBPMW-UHFFFAOYSA-N 0.000 description 1
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- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- XOMVITRPGORDSN-UHFFFAOYSA-N CN(C)CCOCCN(C(O)=O)CCOCCN(C)C Chemical compound CN(C)CCOCCN(C(O)=O)CCOCCN(C)C XOMVITRPGORDSN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
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- 239000005977 Ethylene Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0014—Use of organic additives
- C08J9/0038—Use of organic additives containing phosphorus
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
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- C08J9/125—Water, e.g. hydrated salts
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
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Description
リン酸エステルは、一般式、
(R1−O)3−P=O
を有し、式中、遊離部分R1は、相互に独立に、1個もしくは複数のフェニル基、1個もしくは複数のリン酸基、またはこれらのエステル、ならびに/または窒素、酸素、フッ素、塩素、および臭素からなる群から選択される1個もしくは複数の原子を含む有機部分であり、
ポリホスフェートは、一般式
−[P(O)(O−R‘+)−O]n−
を有し、式中、nは、整数2〜10000であり、R‘+は、アルカリ金属カチオンまたはアンモニウムカチオンであり、
ホスホン酸エステルは、一般式
(R3)(R2−O)2−P=O
を有し、式中、部分R2は、相互に独立に、窒素、酸素、フッ素、塩素、および臭素からなる群から選択される1個もしくは複数の原子を含む有機部分であり、部分R3は、水素、または1〜10個の炭素原子を有する芳香族、脂肪族、もしくは脂環式部分であり、さらなるヘテロ原子を含むことができ、
亜リン酸エステルは、一般式
(R4−O)3−P
を有し、式中、部分R4は、相互に独立に、窒素、酸素、フッ素、塩素、および臭素からなる群から選択される1個もしくは複数の原子を含む有機部分である、ポリウレタンフォームに関する。本発明はさらに、これらのポリウレタンフォームを製造する方法、および自動車内装におけるこれらの使用に関する。
リン酸エステルは、一般式
(R1−O)3−P=O
を有し、式中、3つの部分R1は、相互に独立に、1個もしくは複数のフェニル基、1個もしくは複数のリン酸基、またはこれらのエステル、ならびに/または窒素、酸素、フッ素、塩素、および臭素からなる群から選択される1個もしくは複数の原子を含む有機部分であり、
ポリホスフェートは、一般式
−[P(O)(O−R‘+)−O]n−
を有し、式中、nは、2〜10000の整数であり、R‘+は、アルカリ金属カチオンまたはアンモニウムカチオンであり、
ホスホン酸エステルは、一般式
(R3)(R2−O)2−P=O
を有し、式中、部分R2は、相互に独立に、窒素、酸素、フッ素、塩素、および臭素からなる群から選択される1個もしくは複数の原子を含む有機部分であり、部分R3は、水素、または1〜10個の炭素原子を有する芳香族、脂肪族、もしくは脂環式部分であり、
亜リン酸エステルは、一般式
(R4−O)3−P
を有し、式中、部分R4は、相互に独立に、窒素、酸素、フッ素、塩素、および臭素からなる群から選択される1個もしくは複数の原子を含む有機部分である、ポリウレタンフォームによって達成される。
(R1−O)3−P=O
を有するリン酸のエステルを含み、式中、遊離部分R1は、相互に独立に、1個もしくは複数のフェニル基、1個もしくは複数のフェニル基、1個もしくは複数のリン酸基、またはこれらのエステル、ならびに/または窒素、酸素、フッ素、塩素、および臭素からなる群から選択される1個もしくは複数の原子を含む有機部分である。部分R1はここでそれぞれ好ましくは、相互に独立に、1〜20個、特に好ましくは2〜10個、特に、2〜5個の炭素原子を含み、好ましくは分岐を有する。前記部分は好ましくは、脂肪族である。例えば、OH末端基の形態の、塩素原子または酸素原子を有する部分が好ましい。部分R1の例は、好ましくは2〜10個の繰り返し単位を有する、塩化エチレン、塩化プロピレン、塩化ブチレン、エチレンオキシド、プロピレンオキシド、ブチレンオキシド、およびポリエチルアルキレンオキシドである。
−[P(O)(O−R‘+)−O]n−
の化合物であり、式中、nは、2〜10000の整数であり、R‘+は、アルカリ金属カチオンまたはアンモニウムカチオンである。任意の所望の構造は、末端基、好ましくは一般式の構造としての役割を果たすことができ、
−O−P(O)(O−R‘+)2
式中、R‘+は上記で定義されている通りである。例として、ポリリン酸アンモニウムは、ポリホスフェートとして使用することができる。
(R3)(R2−O)2−P=O
を有する化合物であり、式中、部分R2は、相互に独立に、窒素、酸素、フッ素、塩素、および臭素からなる群から選択される1個もしくは複数の原子を含み、かつ好ましくは分岐を有する有機部分であり、部分R3は、水素、または1〜10個、好ましくは1〜5個、特に、1〜3個の炭素原子を有する芳香族、脂肪族、もしくは脂環式部分であり、これらは任意選択でまた、ヘテロ原子を含む。
(R4−O)3−P
の化合物を含み、式中、部分R4は、相互に独立に、窒素、酸素、フッ素、塩素、および臭素からなる群から選択される1個もしくは複数の原子を含む有機部分である。例えば、OH末端基の形態の、塩素原子または酸素原子を含む部分が好ましい。部分R4はここでそれぞれ好ましくは相互に独立に、1〜20個、特に好ましくは2〜10個、特に、2〜5個の炭素原子を含む。例えば、OH末端基の形態の、塩素原子または酸素原子を含む部分が好ましい。特に、ホスフィットは、OH末端基を含む。部分R4の例は、好ましくは2〜10個の繰り返し単位を有する、塩化エチレン、塩化プロピレン、塩化ブチレン、エチレンオキシド、プロピレンオキシド、ブチレンオキシド、およびポリエチルアルキレンオキシドである。例として、トリス(ジプロピレングリコール)ホスフィットは、亜リン酸エステルとして使用される。
ポリオールA:84%のプロピレンオキシド含量および14%のエチレンオキシド含量を有する、エチレンオキシドおよびプロピレンオキシドをベースとする、35mg KOH/gのOH数および官能性2.7を有するポリエーテロール
ポリオールB:担体ポリオールとしてポリオールAにおいて45%の固体含量を有するグラフトポリオール(スチレン−アクリロニトリル)
MEG:モノエチレングリコール
Isopur SA−21050:ISL−Chemieからのブラックペースト
Polycat15:Air Productsからの触媒
Jeffcat ZF−10:Huntsmanからの触媒
リン化合物
P1:トリス(1,3−ジクロロ−2−イソプロピル)ホスフェート
P2:エチレンオキシド架橋を有するオリゴマーのアルキルホスフェート
P3:ジ(ジエチレングリコール)メチルホスホネート
P4:ClariantからのExolit(登録商標)AP422−ポリリン酸アンモニウム
P5:イソプロピル化トリアリールホスフェート
P6:トリス(ジプロピレングリコール)ホスフィット
P7:トリス(2−ブトキシエチル)ホスフェート
P8:トリス(2−クロロイソプロピル)ホスフェート、TCPP
P9:トリブチルホスフェート(比較)
P10:トリブチルホスフィット(比較)
P11:トリスノニルフェニルホスフィット、TNPP(比較)
P12:Disflamoll(登録商標)TOF−トリス(2−エチルヘキシル)ホスフェート(比較)、Lanxessからの脂肪族ホスフェート
イソシアネート:27.8のNCO含量を有するカルボジイミド−修飾4,4’−MDI
4.8部のポリオールB
8.1部のMEG
5.0部のIsopur SA−21050
0.6部の水
0.8部のPolycat15
0.8部のJeffcat ZF−10
0.25〜2部のリン化合物(表を参照されたい)
Claims (18)
- (a)ポリイソシアネート、
(b)イソシアネートに対して反応性の基を有するポリマー化合物、
(c)イソシアネートに対して反応性の基(複数可)と一緒に、1個または複数の第三級脂肪族アミノ基を有する組み込み可能なアミン触媒を含む触媒であって、少なくとも1個の第三級アミノ基は、メチル部分およびエチル部分から相互に独立に選択される2つの部分を有し、かつまた別の有機部分を有する触媒、
(d)リン酸エステル、および/またはポリホスフェートであって、成分(a)〜(f)の全質量に対する成分(d)の割合は、3質量%未満であるリン酸エステル、および/またはポリホスフェート、
(e)水を含む発泡剤、ならびに任意選択で
(f)連鎖延長剤および/または架橋剤、ならびに
(g)助剤および/または添加剤
を混合して反応混合物を得、反応混合物の反応を完了させてポリウレタンフォームを得ることによって得ることができるポリウレタンフォームであって、
リン酸エステルは、分子内に少なくとも2個のリン酸基を含み、これらは多官能性部分を介した結合を有し、該多官能性部分は、直鎖状または分岐状でよく、及び窒素、酸素、フッ素、塩素、および臭素からなる群から選択される1個もしくは複数の原子を含み、
ポリホスフェートは、一般式
−[P(O)(O−R‘+)−O]n−
を有し、式中、nは、2〜10000の整数であり、R‘+は、アルカリ金属カチオンまたはアンモニウムカチオンである、ポリウレタンフォーム。 - 触媒(c)として組み込み可能なアミン触媒に加えて、単独で有機金属触媒が存在することを特徴とする請求項1に記載のポリウレタンフォーム。
- リン酸エステルが、イソシアネート基に対して反応性の基を含む、請求項1又は2に記載のポリウレタンフォーム。
- 水それ自体が、発泡剤(e)として使用される、請求項1〜3の何れか1項に記載のポリウレタンフォーム。
- 成分(d)が、分子中に少なくとも2個のリン酸基を有する化合物を含む、請求項1から4のいずれか一項に記載のポリウレタンフォーム。
- 100〜850g/Lの平均密度を有するポリウレタンフォームである、請求項1から5のいずれか一項に記載のポリウレタンフォーム。
- 成形されたポリウレタンフォームである、請求項6に記載のポリウレタンフォーム。
- 成形されたポリウレタンフォームの平均密度が、150〜500g/Lである、請求項7に記載のポリウレタンフォーム。
- 自動車の内装パーツである、請求項1から8のいずれか一項に記載のポリウレタンフォーム。
- 自動車の内装パーツが、ステアリングホイール、ダッシュボード、内装ドア外装材、ヘッドレスト、またはコントロールボタンである、請求項9に記載のポリウレタンフォーム。
- さらなる難燃剤を含まない、請求項1から10のいずれか一項に記載のポリウレタンフォーム。
- 成分(d)が、2,2−ビス(クロロメチル)トリメチレンビス(ビス(2−クロロエチル)ホスフェート)を含むことを特徴とする請求項1〜11の何れか1項に記載のポリウレタンフォーム。
- a)ポリイソシアネート、
b)イソシアネートに対して反応性の基を有するポリマー化合物、
c)イソシアネートに対して反応性の基(複数可)と一緒に、1個または複数の第三級脂肪族アミノ基を有する組み込み可能なアミン触媒を含む触媒であって、少なくとも1個の第三級アミノ基は、メチル部分およびエチル部分から相互に独立に選択される2つの部分を有し、かつまた別の有機部分を有する触媒、
d)リン酸エステル、および/またはポリホスフェートであって、成分(a)〜(f)の全質量に対する成分(d)の割合は、3質量%未満であるリン酸エステル、および/またはポリホスフェート、
e)水を含む発泡剤、ならびに任意選択で
f)連鎖延長剤および/または架橋剤、ならびに
g)助剤および/または添加剤
を混合して反応混合物を得、反応混合物の反応を完了させてポリウレタンフォームを得ることによってポリウレタンフォームを製造する方法であって、
リン酸エステルは、分子内に少なくとも2個のリン酸基を含み、これらは多官能性部分を介した結合を有し、該多官能性部分は、直鎖状または分岐状でよく、及び窒素、酸素、フッ素、塩素、および臭素からなる群から選択される1個もしくは複数の原子を含み、
ポリホスフェートは、一般式
−[P(O)(O−R‘+)−O]n−
を有し、式中、nは、2〜10000の整数であり、R‘+は、アルカリ金属カチオンまたはアンモニウムカチオンである、方法。 - 触媒(c)として組み込み可能なアミン触媒に加えて、単独で有機金属触媒が存在することを特徴とする請求項13に記載の方法。
- 自動車内装において、請求項1から12のいずれか一項に記載のポリウレタンフォームを使用する方法。
- (a)ポリイソシアネート、
(b)イソシアネートに対して反応性の基を有するポリマー化合物、
(c)イソシアネートに対して反応性の基(複数可)と一緒に、1個または複数の第三級脂肪族アミノ基を有する組み込み可能なアミン触媒を含む触媒であって、少なくとも1個の第三級アミノ基は、メチル部分およびエチル部分から相互に独立に選択される2つの部分を有し、かつまた別の有機部分を有する触媒、
(d)リン酸エステル、ポリホスフェート、および/またはホスホン酸エステルであって、成分(a)〜(f)の全質量に対する成分(d)の割合は、3質量%未満であるリン酸エステル、ポリホスフェート、および/またはホスホン酸エステル、
(e)水を含む発泡剤、ならびに任意選択で
(f)連鎖延長剤および/または架橋剤、ならびに
(g)助剤および/または添加剤
を混合して反応混合物を得、反応混合物の反応を完了させてポリウレタンフォームを得ることによって得ることができるポリウレタンフォームであって、
リン酸エステルは、分子内に少なくとも2個のリン酸基を含み、これらは多官能性部分を介した結合を有し、該多官能性部分は、直鎖状または分岐状でよく、及び窒素、酸素、フッ素、塩素、および臭素からなる群から選択される1個もしくは複数の原子を含み、
ポリホスフェートは、一般式
−[P(O)(O−R‘+)−O]n−
を有し、式中、nは、2〜10000の整数であり、R‘+は、アルカリ金属カチオンまたはアンモニウムカチオンであり、
ホスホン酸エステルは、一般式
(R3)(R2−O)2−P=O
を有し、式中、部分R2は、相互に独立に、窒素、酸素、フッ素、塩素、および臭素からなる群から選択される1個もしくは複数の原子を含む有機部分であり、部分R3は、水素、または1〜10個の炭素原子を有する芳香族、脂肪族、もしくは脂環式部分である、ポリウレタンフォーム。 - 触媒(c)として組み込み可能なアミン触媒に加えて、単独で有機金属触媒が存在することを特徴とする請求項16に記載のポリウレタンフォーム。
- 成分(d)がホスホン酸エステルを含むことを特徴とする請求項16又は17に記載のポリウレタンフォーム。
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EP12178308.8A EP2690118A1 (de) | 2012-07-27 | 2012-07-27 | Polyurethane enthaltend Phosphorverbindungen |
EP12178308.8 | 2012-07-27 |
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JP2015523493A Division JP2015524499A (ja) | 2012-07-27 | 2013-07-16 | リン化合物を含むポリウレタンフォーム |
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JP (2) | JP2015524499A (ja) |
KR (1) | KR102149805B1 (ja) |
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Families Citing this family (5)
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EP2690118A1 (de) * | 2012-07-27 | 2014-01-29 | Basf Se | Polyurethane enthaltend Phosphorverbindungen |
CZ2015375A3 (cs) | 2015-06-03 | 2016-12-14 | Borcad Cz S.R.O. | Polyurethanová pěna se sníženou hořlavostí, sníženým vývojem kouře a nízkou toxicitou kouře |
EP3495404A1 (de) | 2017-12-07 | 2019-06-12 | Basf Se | Polyurethanschaum |
EP3560970A1 (de) * | 2018-04-25 | 2019-10-30 | Covestro Deutschland AG | Offenzelliger polyurethanhartschaum und dessen verwendung |
CN109369956B (zh) * | 2018-09-21 | 2020-07-31 | 浙江万盛股份有限公司 | 一种聚氨酯泡沫复合阻燃剂及其制备方法 |
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EP2877511A1 (de) | 2015-06-03 |
CN104507991A (zh) | 2015-04-08 |
EP2877511B2 (de) | 2024-03-27 |
CN109503809B (zh) | 2021-08-06 |
EP2690118A1 (de) | 2014-01-29 |
WO2014016167A1 (de) | 2014-01-30 |
JP2015524499A (ja) | 2015-08-24 |
CN109503809A (zh) | 2019-03-22 |
KR20150040996A (ko) | 2015-04-15 |
JP2018111826A (ja) | 2018-07-19 |
EP2877511B1 (de) | 2016-09-14 |
KR102149805B1 (ko) | 2020-08-31 |
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