KR20140042167A - 폴리카보네이트의 제조방법 - Google Patents
폴리카보네이트의 제조방법 Download PDFInfo
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- KR20140042167A KR20140042167A KR1020120108543A KR20120108543A KR20140042167A KR 20140042167 A KR20140042167 A KR 20140042167A KR 1020120108543 A KR1020120108543 A KR 1020120108543A KR 20120108543 A KR20120108543 A KR 20120108543A KR 20140042167 A KR20140042167 A KR 20140042167A
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- Prior art keywords
- carbon atoms
- group
- catalyst
- polycarbonate
- alkyl group
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- 239000004417 polycarbonate Substances 0.000 title claims abstract description 64
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims description 33
- 239000003054 catalyst Substances 0.000 claims abstract description 85
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- 229910052751 metal Inorganic materials 0.000 claims description 78
- 239000002184 metal Substances 0.000 claims description 78
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 40
- 150000002825 nitriles Chemical class 0.000 claims description 37
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000011259 mixed solution Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 239000004593 Epoxy Substances 0.000 claims description 20
- 239000001569 carbon dioxide Substances 0.000 claims description 20
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 20
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 19
- 239000008139 complexing agent Substances 0.000 claims description 19
- 229920000570 polyether Polymers 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000012153 distilled water Substances 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 239000002002 slurry Substances 0.000 claims description 12
- -1 oxybutylene Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229920001400 block copolymer Polymers 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 238000010926 purge Methods 0.000 claims description 3
- 229920005682 EO-PO block copolymer Polymers 0.000 claims description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001925 cycloalkenes Chemical class 0.000 claims description 2
- 229920002557 polyglycidol polymer Polymers 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 abstract 2
- 230000035515 penetration Effects 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 31
- 230000000052 comparative effect Effects 0.000 description 23
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 19
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 10
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 239000004621 biodegradable polymer Substances 0.000 description 3
- 229920002988 biodegradable polymer Polymers 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000003912 environmental pollution Methods 0.000 description 3
- 238000000703 high-speed centrifugation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- GFAZHVHNLUBROE-UHFFFAOYSA-N 1-hydroxybutan-2-one Chemical compound CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 2
- VLJLXEKIAALSJE-UHFFFAOYSA-N 13-oxabicyclo[10.1.0]tridecane Chemical compound C1CCCCCCCCCC2OC21 VLJLXEKIAALSJE-UHFFFAOYSA-N 0.000 description 2
- BNDRWEVUODOUDW-UHFFFAOYSA-N 3-Hydroxy-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)O BNDRWEVUODOUDW-UHFFFAOYSA-N 0.000 description 2
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 2
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- UCFIGPFUCRUDII-UHFFFAOYSA-N [Co](C#N)C#N.[K] Chemical compound [Co](C#N)C#N.[K] UCFIGPFUCRUDII-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229920006351 engineering plastic Polymers 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- CCEFMUBVSUDRLG-KXUCPTDWSA-N (4R)-limonene 1,2-epoxide Natural products C1[C@H](C(=C)C)CC[C@@]2(C)O[C@H]21 CCEFMUBVSUDRLG-KXUCPTDWSA-N 0.000 description 1
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 1
- PYSAJDICZJMKGG-UHFFFAOYSA-N 1-hydroxy-2,2,4-trimethylpentan-3-one Chemical compound CC(C)C(=O)C(C)(C)CO PYSAJDICZJMKGG-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- AIPINVBKJYKCOI-UHFFFAOYSA-N 2,2,6-trichloro-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCC(Cl)(Cl)C2OC21Cl AIPINVBKJYKCOI-UHFFFAOYSA-N 0.000 description 1
- GSKOWRJEBKQTKZ-UHFFFAOYSA-N 2,6-dihydroxy-2,6-dimethylheptan-4-one Chemical compound CC(C)(O)CC(=O)CC(C)(C)O GSKOWRJEBKQTKZ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BVYUAISSKQVRJV-UHFFFAOYSA-N 3-hydroxy-3,5-dimethylhexan-2-one Chemical compound CC(C)CC(C)(O)C(C)=O BVYUAISSKQVRJV-UHFFFAOYSA-N 0.000 description 1
- ZTYFXEDMOYUTCM-UHFFFAOYSA-N 3-hydroxy-3-methylhexan-2-one Chemical compound CCCC(C)(O)C(C)=O ZTYFXEDMOYUTCM-UHFFFAOYSA-N 0.000 description 1
- FDVJISGFGLBDFP-UHFFFAOYSA-N 4,5-dibromo-9-oxabicyclo[6.1.0]nonane Chemical compound C1CC(Br)C(Br)CCC2OC21 FDVJISGFGLBDFP-UHFFFAOYSA-N 0.000 description 1
- YMRDPCUYKKPMFC-UHFFFAOYSA-N 4-hydroxy-2,2,5,5-tetramethylhexan-3-one Chemical compound CC(C)(C)C(O)C(=O)C(C)(C)C YMRDPCUYKKPMFC-UHFFFAOYSA-N 0.000 description 1
- FRWTZJVIDOITHW-UHFFFAOYSA-N 4-hydroxyheptan-3-one Chemical compound CCCC(O)C(=O)CC FRWTZJVIDOITHW-UHFFFAOYSA-N 0.000 description 1
- SKCYVGUCBRYGTE-UHFFFAOYSA-N 4-hydroxyhexan-3-one Chemical compound CCC(O)C(=O)CC SKCYVGUCBRYGTE-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- BVEYJWQCMOVMAR-UHFFFAOYSA-N 5-Hydroxy-4-octanone Chemical compound CCCC(O)C(=O)CCC BVEYJWQCMOVMAR-UHFFFAOYSA-N 0.000 description 1
- ORLDHCIQVZTBQQ-UHFFFAOYSA-N 6-hydroxydecan-5-one Chemical compound CCCCC(O)C(=O)CCCC ORLDHCIQVZTBQQ-UHFFFAOYSA-N 0.000 description 1
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
- MELPJGOMEMRMPL-UHFFFAOYSA-N 9-oxabicyclo[6.1.0]nonane Chemical compound C1CCCCCC2OC21 MELPJGOMEMRMPL-UHFFFAOYSA-N 0.000 description 1
- JJZBBEBDBASNJD-UHFFFAOYSA-N C1C2OC2CC2C(Br)(Br)C21 Chemical compound C1C2OC2CC2C(Br)(Br)C21 JJZBBEBDBASNJD-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- CCEFMUBVSUDRLG-XNWIYYODSA-N Limonene-1,2-epoxide Chemical compound C1[C@H](C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-XNWIYYODSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 229910007541 Zn O Inorganic materials 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019506 cigar Nutrition 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- INDBQWVYFLTCFF-UHFFFAOYSA-L cobalt(2+);dithiocyanate Chemical compound [Co+2].[S-]C#N.[S-]C#N INDBQWVYFLTCFF-UHFFFAOYSA-L 0.000 description 1
- RKBAPHPQTADBIK-UHFFFAOYSA-N cobalt;hexacyanide Chemical compound [Co].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] RKBAPHPQTADBIK-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- JDPQWHLMBJZURR-UHFFFAOYSA-N decan-5-one Chemical compound CCCCCC(=O)CCCC JDPQWHLMBJZURR-UHFFFAOYSA-N 0.000 description 1
- MOWSUOKIHAQPCR-UHFFFAOYSA-N diethoxy-ethyl-[1-(7-oxabicyclo[4.1.0]heptan-4-yl)ethoxy]silane Chemical compound C1C(C(C)O[Si](CC)(OCC)OCC)CCC2OC21 MOWSUOKIHAQPCR-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- CCEFMUBVSUDRLG-UHFFFAOYSA-N limonene-1,2-epoxide Chemical compound C1C(C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-UHFFFAOYSA-N 0.000 description 1
- 229930007453 limonene-1,2-epoxide Natural products 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- MWCFXRVLEYZWBD-UHFFFAOYSA-N tetralithium;iron(2+);hexacyanide Chemical compound [Li+].[Li+].[Li+].[Li+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] MWCFXRVLEYZWBD-UHFFFAOYSA-N 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/32—General preparatory processes using carbon dioxide
- C08G64/34—General preparatory processes using carbon dioxide and cyclic ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
도 2는 일실시예에서 제조된 폴리카보네이트의 푸리에 변환 적외선 분광결과 그래프이다.
도 3은 일실시예에서 제조된 폴리카보네이트의 열중량 분석결과 그래프이다.
촉매 | Zn | Co | Zn/Co |
DMC-E01 | 6.02 | 1.79 | 2.84 |
DMC-5 | 28.96 | 12.08 | 2.40 |
수율(g) | TON | TOF | Tm | GPC | 카보네이트 함량 (%) | |||
ether | carbonate | Mn | PDI | |||||
실시예1 | 18.645 | 20633.11 | 20633.11 | 98.8 | 156.5 | 121,100 | 1.42 | 75.76 |
실세예2 | 19.215 | 21263.89 | 21263.89 | 95.7 | 154.2 | 110,000 | 1.44 | 73.53 |
실시예3 | 20.154 | 22303.02 | 22303.02 | 90.1 | 148.5 | 88,100 | 1.38 | 80.00 |
실시예4 | 20.325 | 22492.25 | 22492.25 | 87.1 | 150.2 | 63,500 | 1.41 | 83.33 |
실시예5 | 20.015 | 22149.20 | 22149.20 | 86.1 | 146.6 | 45,100 | 1.40 | 83.33 |
실시예6 | 21.654 | 23962.96 | 23962.96 | 80.0 | 140.1 | 31,800 | 1.40 | 82.15 |
비교예1 | 13.658 | 3141.86 | 3141.86 | 70.5 | 139.5 | 50,100 | 1.65 | 58.14 |
비교예2 | 14.252 | 3278.51 | 3278.51 | 72.2 | 140.2 | 36,800 | 1.65 | 60.60 |
비교예3 | 14.978 | 3445.52 | 3445.52 | 71.5 | 138.8 | 27,100 | 1.61 | 60.24 |
비교예4 | 14.897 | 3426.88 | 3426.88 | 67.7 | 137.6 | 20,500 | 1.68 | 70.42 |
비교예5 | 15.265 | 3511.54 | 3511.54 | 65.1 | 126.8 | 15,800 | 1.55 | 67.57 |
비교예6 | 17.051 | 3922.38 | 3922.38 | 62.8 | 126.6 | 10,000 | 1.62 | 70.42 |
비교예7 | 5.121 | 1170.95 | 5.121 | 59.9 | 118.8 | 6,800 | 1.57 | 52.63 |
비교예8 | 5.678 | 1306.16 | 5.678 | 62.8 | 101.5 | 3,500 | 1.46 | 55.56 |
비교예9 | 15.875 | 3651.86 | 15.875 | 79.9 | 131.1 | 10,500 | 1.80 | 71.42 |
시간(min) | GPC | 카보네이트 함량(%) |
|
Mn | PDI | ||
1 | 36,600 | 1.42 | 85.47 |
2 | 42,300 | 1.36 | 81.30 |
4 | 43,600 | 1.34 | 83.33 |
7 | 44,900 | 1.30 | 82.64 |
10 | 42,600 | 1.36 | 82.64 |
15 | 40,000 | 1.42 | 84.03 |
20 | 41,700 | 1.37 | 82.64 |
30 | 44,100 | 1.35 | 83.33 |
45 | 41,500 | 1.39 | 81.30 |
60 | 45,100 | 1.40 | 83.33 |
Claims (17)
- 하기 화학식 1의 구조를 포함하는 유기 착화물제, 금속염, 금속시안염 및 폴리에테르 화합물을 포함하는 이중금속시안염 촉매 하에서,
이산화탄소 및 에폭시 화합물을 공중합하여 제조하는 폴리카보네이트의 제조방법:
[화학식 1]
상기 화학식 1에서,
R1은 수소, 탄소수 1 내지 20의 아릴기, 탄소수 1 내지 20의 알킬기 또는 R4-NH-를 나타내고,
R2 및 R3은 각각 독립적으로 수소, 히드록시기, 시아나이드기, 탄소수 1 내지 20의 알킬기 또는 R5-NH-를 나타내고,
R4 및 R5는 각각 독립적으로 수소 또는 탄소수 1 내지 20의 알킬기를 나타내며, n은 0 내지 3이다. - 제 1 항에 있어서,
유기 착화물제는 케톤기 및 히드록시기를 동시에 포함하고 있는 것을 특징으로 하는 폴리카보네이트의 제조방법. - 제 3 항에 있어서,
유기 착화물제는 하나 이상의 알킬기를 더 포함하는 것을 특징으로 하는 폴리카보네이트의 제조방법. - 제 1 항에 있어서,
금속염 및 금속시안염은 물에 용해되어 반응하는 것을 특징으로 하는 폴리카보네이트의 제조방법. - 제 1 항에 있어서,
폴리에테르 화합물은 폴리에테르 폴리올인 것을 특징으로 하는 폴리카보네이트의 제조방법. - 제 5 항에 있어서,
폴리에테르 폴리올은 폴리(프로필렌글리콜) 블록공중합체, 폴리(에틸렌글리콜) 블록공중합체, 폴리테트라메틸렌에테르글리콜 블록공중합체, 에틸렌 옥사이드와 프로필렌 옥사이드의 블록공중합체 또는 산화부틸렌 고분자 및 초분기(hyper branched) 폴리글리시돌 중 1 종 이상을 포함하는 폴리카보네이트의 제조방법. - 하기 화학식 1의 구조를 포함하는 유기 착화물제, 금속염 및 증류수를 포함하는 혼합용액 1을 제조하는 단계;
금속시안염 및 증류수를 포함하는 혼합용액 2를 제조하는 단계;
상기 혼합용액 1과 혼합용액 2를 혼합하여 촉매 슬러리를 제조하는 단계; 및
상기 촉매 슬러리와 하기 화학식 1의 구조를 포함하는 유기 착화물제 및 폴리에테르 혼합물을 혼합하여 반응시키는 단계를 포함하는 이중금속시안염 촉매의 제조방법:
[화학식 1]
상기 화학식 1에서,
R1은 수소, 탄소수 1 내지 20의 아릴기, 탄소수 1 내지 20의 알킬기 또는 R4-NH-를 나타내고,
R2 및 R3은 각각 독립적으로 수소, 히드록시기, 시아나이드기, 탄소수 1 내지 20의 알킬기 또는 R5-NH-를 나타내고,
R4 및 R5는 각각 독립적으로 수소 또는 탄소수 1 내지 20의 알킬기를 나타내며, n은 0 내지 3이다. - 제 7 항에 있어서,
상기 촉매 슬러리와 폴리에테르 혼합물을 혼합하여 반응시키는 단계 이후에 세척 및 건조공정을 더 포함하는 이중금속시안염 촉매의 제조방법. - 제 7 항에 있어서,
이중금속시안염 촉매 100 중량부를 기준으로, 폴리에테르 화합물의 함량은 0.1 내지 30 중량부인 것을 특징으로 하는 이중금속시안염 촉매의 제조방법. - 제 7 항에 있어서,
이중금속시안염 촉매 100 중량부를 기준으로, 금속의 함량은 0.1 내지 10 중량부인 것을 특징으로 하는 이중금속시안염 촉매의 제조방법. - 반응기 내부에 설치된 트랩에 이중금속시안염 촉매를 도입하는 단계;
이산화탄소 가스를 이용하여 반응기 내부를 퍼지하는 단계; 및
에폭시 화합물을 상기 반응기에 주입하여 내부 압력, 온도 및 교반 속도를 조절하는 단계를 포함하는 폴리카보네이트의 제조방법. - 제 12 항에 있어서,
에폭시 화합물은 할로겐기 또는 알콕시기로 치환 또는 비치환된 탄소수 2 내지 20의 알킬렌 옥사이드; 할로겐기 또는 알콕시기로 치환 또는 비치환된 탄소수 4 내지 20의 시클로알켄 옥사이드; 및 할로겐기, 알콕시기 또는 탄소수 2 내지 20의 알킬기로 치환 또는 비치환된 탄소수 1 내지 20의 스티렌 옥사이드로 이루어진 군으로부터 선택된 하나 이상을 포함하는 것을 특징으로 하는 폴리카보네이트의 제조방법. - 제 12 항에 있어서,
에폭시 화합물에 대한 이중금속시안염 촉매의 몰비는 5,000:1 내지 50,000:1인 것을 특징으로 하는 폴리카보네이트의 제조방법. - 제 12 항에 있어서,
반응기의 내부 압력은 10 내지 1,200 psi,
온도는 20 내지 180℃ 및
교반 속도는 최대 600 rpm으로 조절하는 것을 특징으로 하는 폴리카보네이트의 제조방법. - 제 12 항에 있어서,
제조된 폴리카보네이트의 카보네이트 함량은 60 내지 95%인 것을 특징으로 하는 폴리카보네이트의 제조방법. - 제 12 항에 있어서,
제조된 폴리카보네이트의 녹는점은 130 내지 160℃인 것을 특징으로 하는 폴리카보네이트의 제조방법.
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