WO2023054999A1 - 폴리알킬렌 카보네이트 수지의 제조방법 - Google Patents
폴리알킬렌 카보네이트 수지의 제조방법 Download PDFInfo
- Publication number
- WO2023054999A1 WO2023054999A1 PCT/KR2022/014354 KR2022014354W WO2023054999A1 WO 2023054999 A1 WO2023054999 A1 WO 2023054999A1 KR 2022014354 W KR2022014354 W KR 2022014354W WO 2023054999 A1 WO2023054999 A1 WO 2023054999A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cyclohexanol
- formula
- cyclopentanol
- carbonate resin
- polyalkylene carbonate
- Prior art date
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 106
- 239000011347 resin Substances 0.000 title claims abstract description 106
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title claims abstract description 90
- 229920001281 polyalkylene Polymers 0.000 title claims abstract description 81
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 15
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 68
- 239000003054 catalyst Substances 0.000 claims abstract description 61
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 34
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 34
- 150000005676 cyclic carbonates Chemical class 0.000 claims abstract description 14
- -1 cyanide compound Chemical class 0.000 claims description 110
- 125000004432 carbon atom Chemical group C* 0.000 claims description 67
- 229910052751 metal Inorganic materials 0.000 claims description 50
- 239000002184 metal Substances 0.000 claims description 50
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000002947 alkylene group Chemical group 0.000 claims description 30
- 238000006116 polymerization reaction Methods 0.000 claims description 23
- 230000009477 glass transition Effects 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 16
- 239000008139 complexing agent Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical group [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 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 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical compound OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 claims description 9
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims description 9
- RKBAPHPQTADBIK-UHFFFAOYSA-N cobalt;hexacyanide Chemical group [Co].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] RKBAPHPQTADBIK-UHFFFAOYSA-N 0.000 claims description 8
- KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 claims description 8
- FHADSMKORVFYOS-UHFFFAOYSA-N cyclooctanol Chemical compound OC1CCCCCCC1 FHADSMKORVFYOS-UHFFFAOYSA-N 0.000 claims description 8
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 239000011592 zinc chloride Substances 0.000 claims description 7
- 235000005074 zinc chloride Nutrition 0.000 claims description 7
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 claims description 6
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 6
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- RCHLXMOXBJRGNX-UHFFFAOYSA-N 1-butylcyclohexan-1-ol Chemical compound CCCCC1(O)CCCCC1 RCHLXMOXBJRGNX-UHFFFAOYSA-N 0.000 claims description 3
- QVQRKAOFJQBMSF-UHFFFAOYSA-N 2-butylcyclopentan-1-ol Chemical compound CCCCC1CCCC1O QVQRKAOFJQBMSF-UHFFFAOYSA-N 0.000 claims description 3
- IXVGVVQGNQZQGD-UHFFFAOYSA-N 2-propan-2-ylcyclohexan-1-ol Chemical compound CC(C)C1CCCCC1O IXVGVVQGNQZQGD-UHFFFAOYSA-N 0.000 claims description 3
- WMLDVNFSAVPBBH-UHFFFAOYSA-N 3-propan-2-ylcyclohexan-1-ol Chemical compound CC(C)C1CCCC(O)C1 WMLDVNFSAVPBBH-UHFFFAOYSA-N 0.000 claims description 3
- IKOXJOTULSXNNR-UHFFFAOYSA-N 3-propylcyclopentan-1-ol Chemical compound CCCC1CCC(O)C1 IKOXJOTULSXNNR-UHFFFAOYSA-N 0.000 claims description 3
- DKKRDMLKVSKFMJ-UHFFFAOYSA-N 4-propan-2-ylcyclohexan-1-ol Chemical compound CC(C)C1CCC(O)CC1 DKKRDMLKVSKFMJ-UHFFFAOYSA-N 0.000 claims description 3
- CCOQPGVQAWPUPE-UHFFFAOYSA-N 4-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCC(O)CC1 CCOQPGVQAWPUPE-UHFFFAOYSA-N 0.000 claims description 3
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 claims description 3
- INDBQWVYFLTCFF-UHFFFAOYSA-L cobalt(2+);dithiocyanate Chemical compound [Co+2].[S-]C#N.[S-]C#N INDBQWVYFLTCFF-UHFFFAOYSA-L 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910000358 iron sulfate Inorganic materials 0.000 claims description 3
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 3
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 claims description 3
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 claims description 3
- 239000004246 zinc acetate Substances 0.000 claims description 3
- 229940102001 zinc bromide Drugs 0.000 claims description 3
- 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 claims description 3
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 claims description 3
- GQTUSXZITATQAM-UHFFFAOYSA-N 1-butylcyclopentan-1-ol Chemical compound CCCCC1(O)CCCC1 GQTUSXZITATQAM-UHFFFAOYSA-N 0.000 claims description 2
- CAKWRXVKWGUISE-UHFFFAOYSA-N 1-methylcyclopentan-1-ol Chemical compound CC1(O)CCCC1 CAKWRXVKWGUISE-UHFFFAOYSA-N 0.000 claims description 2
- PYLPYOPJKOJRNP-UHFFFAOYSA-N 1-propylcyclohexan-1-ol Chemical compound CCCC1(O)CCCCC1 PYLPYOPJKOJRNP-UHFFFAOYSA-N 0.000 claims description 2
- CKPQAKDCQGMTSO-UHFFFAOYSA-N 2,4-dimethylcyclohexan-1-ol Chemical compound CC1CCC(O)C(C)C1 CKPQAKDCQGMTSO-UHFFFAOYSA-N 0.000 claims description 2
- MNTAIMBGDYAZCM-UHFFFAOYSA-N 2-ethylcyclopentan-1-ol Chemical compound CCC1CCCC1O MNTAIMBGDYAZCM-UHFFFAOYSA-N 0.000 claims description 2
- BVIJQMCYYASIFP-UHFFFAOYSA-N 2-methylcyclopentan-1-ol Chemical compound CC1CCCC1O BVIJQMCYYASIFP-UHFFFAOYSA-N 0.000 claims description 2
- VZBNUCDUQJCIDP-UHFFFAOYSA-N 2-propylcyclohexan-1-ol Chemical compound CCCC1CCCCC1O VZBNUCDUQJCIDP-UHFFFAOYSA-N 0.000 claims description 2
- DLTWBMHADAJAAZ-UHFFFAOYSA-N 2-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCCCC1O DLTWBMHADAJAAZ-UHFFFAOYSA-N 0.000 claims description 2
- CRHZGBUSTWVQAQ-UHFFFAOYSA-N 3-ethylcyclopentan-1-ol Chemical compound CCC1CCC(O)C1 CRHZGBUSTWVQAQ-UHFFFAOYSA-N 0.000 claims description 2
- FVBXFGIVCJUGEG-UHFFFAOYSA-N 3-propylcyclohexan-1-ol Chemical compound CCCC1CCCC(O)C1 FVBXFGIVCJUGEG-UHFFFAOYSA-N 0.000 claims description 2
- GNOXBYBSCDZVMJ-UHFFFAOYSA-N 4-methylcycloheptan-1-ol Chemical compound CC1CCCC(O)CC1 GNOXBYBSCDZVMJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- NLNMBQJPOSCBCN-UHFFFAOYSA-N 1,2-dimethylcyclopentan-1-ol Chemical compound CC1CCCC1(C)O NLNMBQJPOSCBCN-UHFFFAOYSA-N 0.000 claims 1
- VTBOTOBFGSVRMA-UHFFFAOYSA-N 1-Methylcyclohexanol Chemical compound CC1(O)CCCCC1 VTBOTOBFGSVRMA-UHFFFAOYSA-N 0.000 claims 1
- BUCJHJXFXUZJHL-UHFFFAOYSA-N 1-ethylcyclohexan-1-ol Chemical compound CCC1(O)CCCCC1 BUCJHJXFXUZJHL-UHFFFAOYSA-N 0.000 claims 1
- QKFKROULLRFXMV-UHFFFAOYSA-N 3,3-dimethylcyclopentan-1-ol Chemical compound CC1(C)CCC(O)C1 QKFKROULLRFXMV-UHFFFAOYSA-N 0.000 claims 1
- ZBAXJUPCYVIBSP-UHFFFAOYSA-N 3,4-Dimethylcyclohexanol Chemical compound CC1CCC(O)CC1C ZBAXJUPCYVIBSP-UHFFFAOYSA-N 0.000 claims 1
- VEALHWXMCIRWGC-UHFFFAOYSA-N 3-methylcyclopentan-1-ol Chemical compound CC1CCC(O)C1 VEALHWXMCIRWGC-UHFFFAOYSA-N 0.000 claims 1
- YVPZFPKENDZQEJ-UHFFFAOYSA-N 4-propylcyclohexan-1-ol Chemical compound CCCC1CCC(O)CC1 YVPZFPKENDZQEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000853 adhesive Substances 0.000 claims 1
- UETZVSHORCDDTH-UHFFFAOYSA-N iron(2+);hexacyanide Chemical compound [Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] UETZVSHORCDDTH-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 12
- 239000006227 byproduct Substances 0.000 abstract description 8
- 230000000052 comparative effect Effects 0.000 description 33
- 238000002360 preparation method Methods 0.000 description 23
- 239000000126 substance Substances 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 11
- 229920000379 polypropylene carbonate Polymers 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 125000005587 carbonate group Chemical group 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000011259 mixed solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000008188 pellet Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 4
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 229920001515 polyalkylene glycol Polymers 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- PVHCTQIRJHNLMY-UHFFFAOYSA-N 1-propan-2-ylcyclopentan-1-ol Chemical compound CC(C)C1(O)CCCC1 PVHCTQIRJHNLMY-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- KBVVZTBIGBZKGB-UHFFFAOYSA-N 1-ethylcyclohexan-1-ol Chemical compound C(C)C1(CCCCC1)O.C(C)C1(CCCCC1)O KBVVZTBIGBZKGB-UHFFFAOYSA-N 0.000 description 2
- LPCWIFPJLFCXRS-UHFFFAOYSA-N 1-ethylcyclopentan-1-ol Chemical compound CCC1(O)CCCC1 LPCWIFPJLFCXRS-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- JFDMLXYWGLECEY-UHFFFAOYSA-N 2-benzyloxirane Chemical compound C=1C=CC=CC=1CC1CO1 JFDMLXYWGLECEY-UHFFFAOYSA-N 0.000 description 2
- NDVWOBYBJYUSMF-UHFFFAOYSA-N 2-methylcyclohexan-1-ol Chemical compound CC1CCCCC1O NDVWOBYBJYUSMF-UHFFFAOYSA-N 0.000 description 2
- MGXMHKAEHINZOI-UHFFFAOYSA-N 2-propylcyclopentan-1-ol Chemical compound CCCC1CCCC1O MGXMHKAEHINZOI-UHFFFAOYSA-N 0.000 description 2
- DKDFGZYLSAJGRM-UHFFFAOYSA-N 3-butylcyclopentan-1-ol Chemical compound CCCCC1CCC(O)C1 DKDFGZYLSAJGRM-UHFFFAOYSA-N 0.000 description 2
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 2
- BALMGFJTWKIVLD-UHFFFAOYSA-N 3-methylcycloheptan-1-ol Chemical compound CC1CCCCC(O)C1 BALMGFJTWKIVLD-UHFFFAOYSA-N 0.000 description 2
- NPURTPKIWWAXOG-UHFFFAOYSA-N 3-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCCC(O)C1 NPURTPKIWWAXOG-UHFFFAOYSA-N 0.000 description 2
- GUDPJHONHNSJBI-PMMFOGROSA-N C([ClH]([2H])([2H])([2H])([2H])[2H])(Cl)(Cl)[2H] Chemical compound C([ClH]([2H])([2H])([2H])([2H])[2H])(Cl)(Cl)[2H] GUDPJHONHNSJBI-PMMFOGROSA-N 0.000 description 2
- RQDMPKRIUGBJHN-UHFFFAOYSA-N CC1(CCCCC1)O.CC1(CCCCC1)O Chemical compound CC1(CCCCC1)O.CC1(CCCCC1)O RQDMPKRIUGBJHN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RWAADBZWQGAKMD-UHFFFAOYSA-K Cl[Zn](Cl)Cl Chemical compound Cl[Zn](Cl)Cl RWAADBZWQGAKMD-UHFFFAOYSA-K 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001450 anions Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- 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
- C08G64/323—General preparatory processes using carbon dioxide and alcohols
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- 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
- C08G64/18—Block or graft polymers
- C08G64/183—Block or graft polymers containing polyether sequences
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
- B01J27/26—Cyanides
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- 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
- C08G64/02—Aliphatic polycarbonates
-
- 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
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
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- 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
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- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
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- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2663—Metal cyanide catalysts, i.e. DMC's
Definitions
- the present invention relates to a method for preparing a polyalkylene carbonate resin in which the content of cyclic carbonate, which is a by-product, is reduced by increasing the activity of a catalyst and the ratio of repeating units containing carbon dioxide is improved.
- a polyalkylene carbonate resin obtained by polymerization of carbon dioxide and epoxide has been in the limelight as a kind of biodegradable resin.
- the process of producing a polyalkylene carbonate resin using carbon dioxide can reduce the global warming problem in that it fixes carbon dioxide in the atmosphere, and has been actively studied from the viewpoint of using it as a carbon resource.
- a zinc dicarboxylate-based catalyst such as a zinc glutarate catalyst coupled with dicarboxylic acid, Co, Zn ,
- a double metal cyanide catalyst composed of a complex such as Al is used.
- the zinc glutarate catalyst has the advantage of being easy to synthesize and handle, but has a problem in that the amount of catalyst used increases because the activity of the catalyst is very low, and it is difficult to remove the catalyst after polymerization.
- the activity is high, but there is a problem in that the ratio of repeating units containing carbon dioxide in the polymerized polyalkylene carbonate resin is low.
- the present invention is to solve the above problems, and carbon dioxide is polymerized with an alkylene oxide compound and carbon dioxide in the presence of a double metal cyanide catalyst containing a compound represented by Formula 9 as a complexing agent. It is intended to provide a method for producing a polyalkylene carbonate resin having a high proportion of repeating units and a reduced content of cyclic carbonate as a by-product.
- the present invention provides a method for producing a polyalkylene carbonate resin.
- the present invention includes the step of polymerizing an alkylene oxide compound and carbon dioxide in the presence of a catalyst, wherein the catalyst includes a double metal cyanide compound and a complexing agent, and the complexing agent is a compound represented by the following formula (9) , and has a glass transition temperature (Tg) of -10 ° C to 50 ° C, and provides a method for producing a polyalkylene carbonate resin comprising a repeating unit represented by the following formula (1) and a repeating unit represented by the following formula (2):
- R 1 to R 8 are each independently hydrogen, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or a C 3 to 20 carbon atom group.
- x and y are mole fractions, where x is from 0.70 to 1.00, y is from 0.00 to 0.30, and x+y is 1;
- R 9a and R 9b are each independently a single bond or an alkylene group having 1 to 5 carbon atoms, but at least one of R 9a and R 9b is an alkylene group having 1 to 5 carbon atoms;
- R 9c and R 9d are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
- n is an integer from 0 to 2;
- the present invention provides a method for producing a polyalkylene carbonate resin according to (1) above, wherein the polymerization is carried out in a temperature range of 30 ° C to 120 ° C.
- the present invention provides a method for preparing a polyalkylene carbonate resin according to (1) or (2) above, wherein the polymerization is carried out at a pressure range of 5 bar to 50 bar.
- the compound represented by Formula 9 is cyclobutanol, cyclopentanol, cyclohexanol, cycloheptane Cycloheptanol), Cyclooctanol, 1-ethyl cyclopentanol, 1-methyl cyclopentanol, 2-methyl cyclopentanol, 3 -methyl cyclopentanol (3-methyl cyclopentanol), 1-ethyl cyclopentanol (1-ethyl cyclopentanol), 2-ethyl cyclopentanol (2-ethyl cyclopentanol), 3-ethyl cyclopentanol (3-ethyl cyclopentanol) , 1-propyl cyclopentanol, 2-propyl cyclopentanol, 3-propyl cyclopentanol, 1-butyl cyclopentanol cyclopentanol cyclohexanol,
- the compound represented by Formula 9 is cyclobutanol, cyclopentanol, cyclohexanol, cycloheptane It provides a method for producing a polyalkylene carbonate resin that is at least one selected from the group consisting of Cycloheptanol, and Cyclooctanol.
- the present invention provides a method for producing a polyalkylene carbonate resin according to any one of (1) to (5) above, wherein the double metal cyanide compound is derived from a metal cyanide complex salt and a metal salt.
- the metal cyanide complex salt is potassium hexacyanocobaltate (Potassium hexacyanocobaltate (III)), potassium hexacyanoferrate (Potassium hexacyanoferrate (II)), potassium hexacyanate Anoferrate (Potassium hexacyanoferrate (III)), calcium hexacyanocobaltate (Calcium hexacyanoferrate (III) or lithium hexacyanoiridate (Lithium hexacyanoiridate (III))
- a method for producing a polyalkylene carbonate resin do is potassium hexacyanocobaltate (Potassium hexacyanocobaltate (III)), potassium hexacyanoferrate (Potassium hexacyanoferrate (II)), potassium hexacyanate Anoferrate (Potassium hexacyanoferrate (III)), calcium hex
- the metal salt is zinc (II) chloride, zinc (III) chloride, zinc bromide, zinc iodide, zinc acetate, zinc acetylacetonate, zinc benzoate, zinc nitrate, iron sulfate (II), iron bromide (II), cobalt chloride (II), cobalt thiocyanate (II), nickel formate (II) and nickel (II) nitrate polyalkylene carbonate resin of at least one member selected from the group consisting of Provides a manufacturing method of.
- the present invention according to any one of (1) to (8) above, wherein the catalyst further comprises an adhering agent, and the adhering agent is a compound having a hydroxyl group, an amine group, an ester group, or an ether group at the terminal. It provides a method for producing a polyalkylene carbonate resin.
- the present invention provides a method for producing a polyalkylene carbonate resin according to any one of (1) to (9), wherein x is 0.90 to 1.00 and y is 0.00 to 0.10.
- R 1 to R 8 are each independently a linear alkyl group having 1 to 20 carbon atoms, or a linear alkyl group having 3 to 20 carbon atoms.
- a branched alkyl group, an aryl group having 6 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or a cycloalkyl group having 3 to 20 carbon atoms, and a polyalkylene carbonate resin having a glass transition temperature (Tg) of 30 ° C to 50 ° C Provides a manufacturing method of.
- the present invention provides a method for producing a polyalkylene carbonate resin according to any one of (1) to (12), wherein the repeating unit represented by Formula 1 is represented by Formula 3 below:
- R 1 to R 4 are each independently hydrogen or a linear alkyl group having 1 to 10 carbon atoms, and x and * are as defined in Formula 1 above.
- the present invention provides a method for producing a polyalkylene carbonate resin according to any one of (1) to (13) above, wherein the repeating unit represented by Formula 1 is represented by Formula 4 or Formula 5 below do.
- the present invention provides a method for preparing a polyalkylene carbonate resin according to any one of (1) to (14) above, wherein the repeating unit represented by Chemical Formula 2 is represented by Chemical Formula 6 below.
- R 5 to R 8 are each independently hydrogen or a linear alkyl group having 1 to 10 carbon atoms, and y and * are as defined in Formula 2 above.
- the present invention provides a method for producing a polyalkylene carbonate resin according to any one of (1) to (15) above, wherein the repeating unit represented by Formula 2 is represented by Formula 7 or Formula 8 below do.
- the present invention is the polyalkylene carbonate according to any one of (1) to (16), wherein the content of the cyclic carbonate is 0.5 wt% to 15.0 wt% based on the total weight of the polyalkylene carbonate resin. provide resin.
- the method for producing a polyalkylene carbonate resin according to the present invention includes carbon dioxide by polymerizing an alkylene oxide compound and carbon dioxide in the presence of a double metal cyanide catalyst containing a compound represented by Formula 9 as a complexing agent. It is possible to prepare a polyalkylene carbonate resin having an increased ratio of repeating units, reduced content of cyclic carbonate as a by-product, and increased glass transition temperature.
- alkyl group used in the present invention may mean a monovalent aliphatic saturated hydrocarbon.
- aryl group used in the present invention may mean a cyclic aromatic hydrocarbon, and also a monocyclic aromatic hydrocarbon in which one ring is formed, or a polycyclic aromatic hydrocarbon in which two or more rings are bonded. It may mean including all.
- alkenyl group used in the present invention may mean a monovalent aliphatic unsaturated hydrocarbon containing one or two or more double bonds.
- cycloalkyl group used in the present invention may include all saturated cyclic hydrocarbons or cyclic unsaturated hydrocarbons containing one or two or more unsaturated bonds.
- the present invention provides a method for producing a polyalkylene carbonate resin having a glass transition temperature (Tg) of -10°C to 50°C and including a repeating unit represented by Formula 1 below and a repeating unit represented by Formula 2 below.
- Tg glass transition temperature
- R 1 to R 8 are each independently hydrogen, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or an alkenyl group having 3 to 20 carbon atoms.
- x and y are mole fractions, where x is 0.70 to 1.00, y is 0.00 to 0.30, and x+y is 1.
- the method for preparing a polyalkylene carbonate resin according to an embodiment of the present invention includes polymerizing an alkylene oxide compound and carbon dioxide in the presence of a catalyst, wherein the catalyst includes a double metal cyanide compound and a complexing agent, ,
- the complexing agent may be a compound represented by Formula 9 below.
- R 9a and R 9b are each independently a single bond or an alkylene group having 1 to 5 carbon atoms, but at least one of R 9a and R 9b is an alkylene group having 1 to 5 carbon atoms;
- R 9c and R 9d are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
- n is an integer from 0 to 2;
- the double metal cyanide catalyst uses ethanol, isopropanol, normal butanol, isobutanol, sec-butanol, tert-butanol, or the like, or a polyalkylene glycol-based material to improve the catalyst activity.
- tert-butanol as a complexing agent has been most widely used to prepare a double metal cyanide catalyst, but when polyalkylene carbonate resin is polymerized under a double metal cyanide catalyst prepared using tert-butanol, the polymerized There was a problem that the ratio of repeating units containing carbon dioxide in the polyalkylene carbonate resin was low.
- a double metal cyanide catalyst containing a C2 to C20 unsaturated alcohol capable of having a cycloalkyl group as a complexing ligand in order to increase the ratio of repeating units containing carbon dioxide in a polymer obtained by copolymerization of alkylene oxide and carbon dioxide
- it was used as the copolymerization catalyst, but improvement in the ratio of repeating units containing carbon dioxide in the produced polymer was insignificant.
- a double metal cyanide catalyst containing a cyclic polyol has been used as a complexing agent. There is a problem that other complexing agents such as tert-butanediol are not used, and in addition, the ratio of repeating units containing carbon dioxide in the polymer produced is still not high.
- the double metal cyanide catalyst of the present invention is prepared using a cycloalkane type alcohol having a bulky structure as a complexing agent, and thus, cubic, amorphous and monoclinic
- the crystal structure of the catalyst may be variously configured, and thus, there is an effect of appropriately adjusting the reaction rate of the epoxide compound and carbon dioxide.
- the catalyst according to an embodiment of the present invention includes a compound represented by Formula 9 as a complexing agent, and in Formula 9, R 9a and R 9b are each independently a single bond or an alkyl having 1 to 3 carbon atoms.
- R 9a and R 9b are each independently a single bond or an alkyl having 1 to 3 carbon atoms.
- R 9s and R 9b are each independently a single bond or an alkylene group having 1 to 3 carbon atoms, but at least one of R 9a and R 9b is an alkylene group having 1 to 3 carbon atoms, and R 9c is a hydrogen atom, and n may be 0.
- the complexing agent may be a cycloalkyl alcohol having 3 to 12 carbon atoms, and specifically, a cycloalkyl alcohol having 4 to 10 carbon atoms or 5 to 7 carbon atoms.
- the compound represented by Formula 9 is cyclobutanol, cyclopentanol, cyclohexanol, cycloheptanol, cyclooctanol, 1-ethyl cyclo Pentanol (1-ethyl cyclopentanol), 1-methyl cyclopentanol (1-methyl cyclopentanol), 2-methyl cyclopentanol (2-methyl cyclopentanol), 3-methyl cyclopentanol (3-methyl cyclopentanol), 1- 1-ethyl cyclopentanol, 2-ethyl cyclopentanol, 3-ethyl cyclopentanol, 1-propyl cylopentanol, 2-propyl cyclopentanol, 3-propyl cyclopentanol, 1-butyl cyclopentanol, 2-butyl cyclopentanol ), 3-butyl cyclopentanol, 1-e
- the compound represented by Formula 9 is a group consisting of cyclobutanol, cyclopentanol, cyclohexanol, cycloheptanol, and cyclooctanol. It may be any one or more selected from.
- the catalyst includes a double metal cyanide compound
- the double metal cyanide compound may be derived from a metal cyanide complex salt and a metal salt, and the metal cyanide complex salt may exhibit water solubility.
- the metal cyanide complex salt may be represented by Chemical Formula 10 below.
- M ⁇ is Fe(II), Fe(III), Co(II), Co(III), Cr(II), Cr(III), Mn(II), Mn(III), Ir( III), Ni(II), Rh(III), Ru(II), V(V), and V(IV), and preferably at least one selected from the group consisting of Co(II), Co(III), At least one may be selected from the group consisting of Fe(II), Fe(III), Cr(III), Ir(III) and Ni(II).
- Y is an alkali metal ion or an alkaline earth metal ion.
- a is an integer from 1 to 4
- b is an integer from 4 to 6
- the values of a and b are selected such that the metal cyanide complex salt is electrically neutral.
- the metal cyanide complex salt is potassium hexacyanocobaltate (Potassium hexacyanocobaltate (III)), potassium hexacyanoferrate (Potassium hexacyanoferrate (II)), potassium hexacyanoferrate (Potassium hexacyanoferrate (III) ), calcium hexacyanoferrate (III) or lithium hexacyanoiridate (III), preferably potassium hexacyanocobaltate (Potassium hexacyanocobaltate (III)) there is.
- the metal salt may exhibit water solubility.
- the metal salt may be represented by Formula 11 below.
- M is a transition metal, preferably Zn(II), Fe(II), Ni(II), Mn(II), Co(II), Sn(II), Pb(II), Fe (III), Mo(IV), Mo(VI), Al(III), V(V), V(IV), Sr(II), W(IV).
- At least one may be selected from the group consisting of W(VI), Cu(II) and Cr(III), more preferably Zn(II), Fe(II), Co(II) and Ni(II)
- X is an anion selected from halides, hydroxides, sulfates, carbonates, cyanates, oxalates, thiocyanates, isocyanates, isothiocyanates, carboxylates, and nitrates.
- the value of n is a number that satisfies the valence state of M.
- the metal salt is zinc chloride (II), zinc chloride (III), zinc bromide, zinc iodide, zinc acetate, zinc acetylacetonate, zinc benzoate, zinc nitrate, iron sulfate (II), iron bromide (II) , cobalt (II) chloride, cobalt (II) thiocyanate, nickel (II) formate, nickel (II) nitrate, and mixtures thereof, preferably zinc (II) chloride, zinc (III) chloride, bromide It may be zinc or zinc iodide.
- the catalyst according to the present invention may be represented by Formula 12 below.
- M 1 and M 2 are each independently a transition metal
- X is an anion
- L is cyclobutanol, cyclopentanol, cyclohexanol, cycloheptanol, or cyclooctanol.
- p, q, d, r, e and f are each independently an integer of 1 to 6.
- the catalyst according to the present invention may be represented by Formula 13 below.
- L is cyclobutanol, cyclopentanol, cyclohexanol, cycloheptanol, or cyclooctanol, and g, h and i are each independently an integer of 1 to 6.
- the catalyst of the present invention may further include an attachment agent, and the attachment agent may be a compound having a hydroxyl group, an amine group, an ester group, or an ether group at the terminal.
- the attachment agent may improve the activity of the catalyst, and for example, polyacrylamide, poly(acrylamide-co-acrylic acid), polyacrylic acid, poly(acrylic acid-co-maleic acid), polyacrylonitrile, polyalkyl Acrylates, polyalkyl methacrylates, polyvinyl methyl ether, polyvinyl ethyl ether, polyvinyl acetate, polyvinyl alcohol, poly-N-vinylpyrrolidone, poly(N-vinylpyrrolidone-co-acrylic acid), Polyvinyl methyl ketone, poly(4-vinylphenol), poly(acrylic acid-co-styrene), oxazoline polymer, polyalkylenimine, maleic acid, maleic anhydride copolymer, hydroxyethylcellulose, polyacetal, glycy It may be at least one selected from the group consisting of diyl ether, glycoside, carboxylic acid ester of polyhydric alcohol, gallic acid, ester
- the attaching agent may be a compound prepared by ring-opening polymerization of a cyclic ether compound, an epoxy polymer or an oxetane polymer, for example, polyether, polyester, polycarbonate, polyalkylene glycol, polyalkylene glycol It may be at least one selected from the group consisting of sorbitan esters and polyalkylene glycol glycidyl ethers.
- the polyalkylene carbonate resin of the present invention is prepared by polymerizing an alkylene oxide compound and carbon dioxide, and the polymerization method is not particularly limited, but may preferably be carried out by solution polymerization.
- the heat of reaction can be appropriately controlled, and the weight average molecular weight or viscosity of the polyalkylene carbonate resin to be obtained can be easily controlled.
- the catalyst and the alkylene oxide compound may be used in a weight ratio of 1:100 to 1:8000, 1:300 to 1:6000, or 1:1000 to 1:4000. It is possible to minimize by-products while exhibiting high catalytic activity within the above-described range, and there is an effect of minimizing a back-biting phenomenon of the polyalkylene carbonate resin prepared by heating.
- the polymerization of the alkylene oxide compound and carbon dioxide may be carried out at a temperature range of 30 °C to 120 °C, 40 °C to 110 °C, or 50 °C to 100 °C.
- the polymerization time of the alkylene oxide compound and carbon dioxide can be managed within 24 hours, thereby improving manufacturing productivity.
- the polymerization of the alkylene oxide compound and carbon dioxide may be carried out in a pressure range of 5 bar to 50 bar, 10 bar to 40 bar, or 15 bar to 30 bar.
- the ratio of repeating units containing carbon dioxide is high in the prepared polyalkylene carbonate resin, and the content of cyclic carbonate as a by-product is reduced.
- the alkylene oxide compound may be an alkylene oxide having 2 to 20 carbon atoms unsubstituted or substituted with a halogen or an alkyl group having 1 to 5 carbon atoms; cycloalkylene oxide having 4 to 20 carbon atoms unsubstituted or substituted with a halogen or an alkyl group having 1 to 5 carbon atoms; And any one or more compounds selected from the group consisting of styrene oxide having 8 to 20 carbon atoms substituted or unsubstituted with a halogen or an alkyl group having 1 to 5 carbon atoms may be used.
- the alkylene oxide compound and the solvent may be mixed, and the solvent includes methylene chloride, ethylene dichloride, trichloroethane, tetrachloroethane, chloroform, Acetonitrile, propionitrile, dimethylformamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, nitromethane, 1,4-dioxane, hexane, toluene, tetrahydrofuran, methyl ethyl ketone, methyl amine ketone , methyl isobutyl ketone, acetone, cyclohexanone, trichloroethylene, methyl acetate, vinyl acetate, ethyl acetate, propyl acetate, butilolactone, caprolactone, nitropropane, benzene, styrene, x
- the solvent and the alkylene oxide compound may be used in a weight ratio of 1:0.1 to 1:100, 1:1 to 1:100, or 1:1 to 1:10. Within this range, the solvent can properly act as a reaction medium, thereby improving the productivity of the polyalkylene carbonate resin and minimizing by-products generated in the manufacturing process.
- the polyalkylene carbonate resin prepared by the above production method according to an embodiment of the present invention has a glass transition temperature (Tg) of -10 °C to 50 °C, repeating units represented by the following formula (1) and formula (2) It may include a repeating unit represented by
- the polyalkylene carbonate resin prepared from the above production method according to an embodiment of the present invention has a glass transition temperature (Tg) of -10 ° C to 50 ° C, and a repeating unit represented by the following formula (1) and the following formula (2) contains repeating units.
- R 1 to R 8 are each independently selected from hydrogen, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an alkene having 2 to 20 carbon atoms.
- branched alkyl group may mean all that exhibits a branched form in the state in which the branched alkyl group is bound.
- the x may be 0.80 to 1.00, y may be 0.00 to 0.20, preferably, the x may be 0.90 to 1.00, and y may be 0.00 to 0.10.
- the fixed ratio of carbon dioxide is high, so it is effective in reducing greenhouse gases and is advantageous in terms of biodegradation characteristics.
- the polyalkylene carbonate resin according to the present invention is made into a film, the film exhibits low oxygen permeability, thereby having excellent barrier properties.
- the polyalkylene carbonate resin may include polyethylene carbonate resin, polypropylene carbonate resin, polypentene carbonate resin, polyhexene carbonate resin, polyoctene carbonate resin, polycyclohexene carbonate resin, or a copolymer thereof.
- R 1 to R 8 are each independently hydrogen, a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or a cycloalkyl group having 3 to 20 carbon atoms, and may be selected as an appropriate functional group in consideration of physical properties of a resin to be finally obtained.
- repeating unit represented by Chemical Formula 1 may be represented by Chemical Formula 3 below.
- R 1 to R 4 are each independently hydrogen or a linear alkyl group having 1 to 10 carbon atoms, and x and * are as defined in Formula 1 above.
- repeating unit represented by Chemical Formula 1 may be represented by Chemical Formula 4 or Chemical Formula 5 below.
- repeating unit represented by Chemical Formula 2 may be represented by Chemical Formula 6 below.
- R 5 to R 8 are each independently hydrogen or a linear alkyl group having 1 to 10 carbon atoms, and y and * are as defined in Formula 2 above.
- repeating unit represented by Chemical Formula 2 may be represented by Chemical Formula 7 or Chemical Formula 8 below.
- the polyalkylene carbonate resin of the present invention has a glass transition temperature (Tg) of -10 °C to 50 °C, 0 °C to 50 °C, or 10 °C to 50 °C. When the above range is satisfied, the processability of the polyalkylene carbonate resin may be excellent at room temperature.
- Tg glass transition temperature
- R 1 to R 8 are each independently hydrogen, the glass transition temperature (Tg) is 0 °C to 20 °C, or 0 °C to 15 may be °C.
- R 1 to R 8 are each independently a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, or a C 6 to 20 carbon atom group.
- the glass transition temperature (Tg) may be 30 °C to 50 °C or 35 °C to 50 °C.
- the content of the cyclic carbonate may be 0.5 wt% to 15.0 wt%, 0.5 wt% to 10.0 wt%, or 0.5 wt% to 5.0 wt% based on the total weight of the polyalkylene carbonate resin of the present invention.
- the problem of lowering the glass transition temperature due to the cyclic carbonate acting as a softener can be minimized, so that excellent mechanical properties are obtained.
- the cyclic carbonate content can be measured by dissolving 10 mg of a polyalkylene carbonate resin sample in a chloroform-d 6 solvent using a 1 H-NMR spectrometer (500 MHz Spectrometer, Jeol Co.). Specifically, from the results measured by 1 H-NMR spectrometer, it was confirmed that the peak appeared at around 4.5 ppm, which is the cyclic carbonate peak, and the cyclic carbonate content was calculated as shown in Equation 1 below using the carbonate peak area and ether peak area can be calculated.
- Equation 1 the contents of A, B, C, N and CO 2 may be defined as follows.
- A cyclic carbonate peak area
- B carbonate peak area
- C ether peak area
- N [alkylene oxide molar mass/(44 + alkylene oxide molar mass)]
- CO 2 content (molar fraction of carbonate units ⁇ 44)/[(mol fraction of carbonate units ⁇ 44) + (molar mass of alkylene oxide ⁇ 100)]
- a first mixed solution was prepared by mixing 11.45 g of zinc chloride, 30 ml of distilled water, and 39 g of cyclohexanol in a first 500 ml beaker.
- a second mixed solution was prepared by dissolving 4 g of potassium hexacyanocobaltate in 100 ml of distilled water in a second 250 ml beaker.
- the third mixed solution was added at once and reacted for 1 hour. Thereafter, the mixed product was separated using high-speed centrifugation, and the separated precipitate was washed twice using a mixture of 70 ml of distilled water and 70 ml of cyclohexanol. Thereafter, after additional washing with 140 ml of cyclohexanol, the washed precipitate was dried in a vacuum oven at 80° C. for 12 hours to finally obtain 6.2 g of a double metal cyanide catalyst.
- Example 1 except for using propylene oxide instead of ethylene oxide, it was carried out in the same manner as in Example 1, and finally 32.29 g of polypropylene carbonate resin was obtained.
- Example 1 the polymerization reaction was carried out in the same manner as in Example 1 except that the polymerization was carried out at 85 °C instead of 65 °C, and finally 25.6 g of polyethylene carbonate was obtained.
- Example 3 was carried out in the same manner as in Example 3 except for using propylene oxide instead of ethylene oxide, and finally 30.5 g of polypropylene carbonate resin was obtained.
- Example 1 the polymerization reaction was carried out in the same manner as in Example 1, except that the polymerization was carried out at 105 °C instead of 65 °C, and finally 22.8 g of polyethylene carbonate was obtained.
- Example 5 was carried out in the same manner as in Example 5, except for using propylene oxide instead of ethylene oxide, and finally 23.2 g of polypropylene carbonate resin was obtained.
- Example 3 was carried out in the same manner as in Example 3, except that the double metal cyanide catalyst prepared in Preparation Example 2 was used instead of the double metal cyanide catalyst prepared in Preparation Example 1, and finally 30.0 g of A polyethylene carbonate resin was obtained.
- Example 7 propylene oxide was used instead of ethylene oxide, and the polymerization was carried out in the same manner as in Example 7, except that the polymerization was carried out at 105 ° C instead of 85 ° C, and finally 30.7 g of polyethylene carbonate obtained.
- Example 1 was carried out in the same manner as in Example 1, except that the double metal cyanide catalyst prepared in Comparative Preparation Example 1 was used instead of the double metal cyanide catalyst prepared in Preparation Example 1, and finally 8.15 g A polyethylene carbonate resin of was obtained.
- Comparative Example 1 except for using propylene oxide instead of ethylene oxide, the same method as in Comparative Example 1 was performed, and finally 10.2 g of polypropylene carbonate resin was obtained.
- Comparative Example 1 the polymerization was carried out in the same manner as in Comparative Example 1, except that the polymerization was carried out at 85 °C instead of 65 °C, and finally 11.7 g of polyethylene carbonate was obtained.
- Comparative Example 3 except for using propylene oxide instead of ethylene oxide, the same method as in Comparative Example 3 was performed, and finally 23.6 g of polypropylene carbonate resin was obtained.
- Comparative Example 1 the polymerization was carried out in the same manner as in Comparative Example 1, except that the polymerization was carried out at 105 °C instead of 65 °C, and finally 13.4 g of polyethylene carbonate was obtained.
- Comparative Example 5 except for using propylene oxide instead of ethylene oxide, the same method as in Comparative Example 5 was performed, and finally 23.2 g of polypropylene carbonate resin was obtained.
- Example 3 was carried out in the same manner as in Example 3, except that the double metal cyanide catalyst prepared in Comparative Preparation Example 2 was used instead of the double metal cyanide catalyst prepared in Preparation Example 1, and finally 12.1 g A polyethylene carbonate resin of was obtained.
- Example 3 was carried out in the same manner as in Example 3, except that the double metal cyanide catalyst prepared in Comparative Preparation Example 3 was used instead of the double metal cyanide catalyst prepared in Preparation Example 1, but an effective amount of polyethylene carbonate No resin was obtained.
- the types of alkylene oxide compounds used in Examples 1 to 8 and Comparative Examples 1 to 8, the composition of the catalyst, and the polymerization temperature of the polyalkylene carbonate resin are shown in Table 1 below.
- the activities of the catalysts used in Examples 1 to 8 and Comparative Examples 1 to 8 were measured and are shown in Table 1 below.
- the carbonate unit mole fraction and glass transition temperature of the polyalkylene carbonate resins obtained in Examples 1 to 8 and Comparative Examples 1 to 8 were measured and shown in Tables 1 and 2 below.
- Catalyst activity (g-polymer/g-catalyst): The weight of the polymerized polyalkylene carbonate resin and the amount of catalyst used were measured. Catalytic activity was calculated according to Equation 2 below using the measured values.
- Mole fraction of carbonate units [(carbonate peak area)/(carbonate peak area + ether peak area)] ⁇ 100
- Films were prepared using each resin and processability was evaluated according to the degree of film formation.
- the film was prepared by placing 4 g of each polyalkylene carbonate resin on a hot press preheated to 180° C., compressing at 1 MPa for 5 minutes, and then compressing at 5 MPa for 1 minute.
- a uniform and flat film was produced, it was marked as ⁇ , and when a uniform and flat film was not produced due to sticking to the press, it was marked as X.
- Pellets were prepared using each resin, and processability was evaluated by an anti-blocking test.
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Abstract
Description
Claims (17)
- 촉매의 존재 하에 알킬렌 옥사이드 화합물 및 이산화탄소를 중합하는 단계를 포함하고,상기 촉매는 이중 금속 시아나이드 화합물 및 착화제를 포함하고,상기 착화제는 하기 화학식 9로 표시되는 화합물인 것이며,유리전이온도(Tg)가 -10℃ 내지 50℃이고, 하기 화학식 1로 표시되는 반복단위 및 하기 화학식 2로 표시되는 반복단위를 포함하는 폴리알킬렌 카보네이트 수지의 제조방법:[화학식 1][화학식 2]상기 화학식 1 및 화학식 2에서,R1 내지 R8은 각각 독립적으로 수소, 탄소수 1 내지 20의 선형 알킬기, 탄소수 3 내지 20의 분지형 알킬기, 탄소수 6 내지 20의 아릴기, 탄소수 2 내지 20의 알케닐기, 또는 탄소수 3 내지 20의 사이클로알킬기이고,*는 반복단위 간 연결 부위를 의미하며,x 및 y는 몰분율로서, x는 0.70 내지 1.00이고, y는 0.00 내지 0.30이며, x+y는 1이고,[화학식 9]R9a 및 R9b는 서로 독립적으로 단일결합 또는 탄소수 1 내지 5의 알킬렌기이되, R9a 및 R9b 중 적어도 하나는 탄소수 1 내지 5의 알킬렌기이고,R9c 및 R9d는 서로 독립적으로 수소원자 또는 탄소수 1 내지 6의 알킬기이며,n은 0 내지 2의 정수이다.
- 제1항에 있어서,상기 중합은 30℃ 내지 120℃의 온도범위에서 실시되는 것인 폴리알킬렌 카보네이트 수지의 제조방법.
- 제1항에 있어서,상기 중합은 5 bar 내지 50 bar의 압력범위에서 실시되는 것인 폴리알킬렌 카보네이트 수지의 제조방법.
- 제1항에 있어서,상기 화학식 9로 표시되는 화합물은 사이클로부탄올(Cyclobutanol), 사이클로펜탄올(Cyclopentanol), 사이클로헥산올(Cyclohexanol), 사이클로헵탄올 Cycloheptanol), 사이클로옥탄올(Cyclooctanol), 1-에틸 사이클로펜타놀(1-ethyl cyclopentanol), 1-메틸 사이클로펜타놀(1-methyl cyclopentanol) 2-메틸 사이클로펜타놀(2-methyl cyclopentanol), 3-메틸 사이클로펜타놀(3-methyl cyclopentanol), 1-에틸 사이클로펜타놀(1-ethyl cyclopentanol), 2-에틸 사이클로펜타놀(2-ethyl cyclopentanol), 3-에틸 사이클로펜타놀(3-ethyl cyclopentanol), 1-프로필 사이클로펜타놀(1-propyl cylopentanol), 2-프로필 사이클로펜타놀(2-propyl cyclopentanol), 3-프로필 사이클로펜타놀(3-propyl cyclopentanol), 1-부틸 사이클로펜타놀(1-butyl cyclopentanol), 2-부틸 사이클로펜타놀(2-butyl cyclopentanol), 3-부틸 사이클로펜타놀(3-butyl cyclopentanol), 1-이소프로필 사이클로펜타놀(1-isopropyl cyclopentanol), 2-이소프로필 사이클로펜타놀(2-isopropyl cyclopentanol), 3-이소프로필 사이클로펜타놀(3-isopropyl cyclopentanol), 1-프로판-2-일 사이클로펜타놀(1-(propan-2-yl) cyclopentanol), 2,2-디메틸 사이클로펜타놀(2,2-dimethyl cyclopentanol), 2,3-디메틸 사이클로펜타놀(2,3-dimethyl cyclopentanol), 3,3-디메틸 사이클로펜타놀(3,3-dimethyl cyclopentanol), 1,2-디메틸 사이클로펜타놀(1,2-dimethyl cyclopentanol), 1,3-디메틸 사이클로펜타놀(1,3-dimethyl cyclopentanol), 1-메틸 사이클로헥산올(1-methyl cyclohexanol), 1-에틸 사이클로헥산올(1-ethyl cyclohexanol), 1-프로필 사이클로헥산올(1-propyl cyclohexanol), 1-부틸 사이클로헥산올(1-butyl cylohexanol), 2-메틸-1-사이클로헥산올(2-methyl-1-cyclohexanol), 2-에틸-1-사이클로헥산올(2-ethyl-1-cyclohexanol), 3-에틸-1-사이클로헥산올(3-ethyl-1-cyclohexanol), 4-에틸-1-사이클로헥산올(4-ethyl-1-cyclohexanol), 2-프로필-1-사이클로헥산올(2-propy-1-cyclohexanol), 3-프로필-1-사이클로헥산올(3-propyl-1-cyclohexanol), 4-프로필-1-사이클로헥산올(4-propyl-1-cyclohexanol), 2-부틸-1-사이클로헥산올(2-butyl-1-cyclohexanol), 3-부틸-1-사이클로헥산올(3-butyl-1-cyclohexanol), 4-부틸-1-사이클로헥산올(4-butyl-1-cyclohexanol), 2-이소프로필-1-사이클로헥산올(2-isopropyl-1-cyclohexanol), 3-이소프로필-1-사이클로헥산올(3-isopropyl-1-cyclohexanol), 4-이소프로필-1-사이클로헥산올(4-isopropyl-1-cyclohexanol), 2-tert-부틸-1-사이클로헥산올(2-tert-butyl-1-cyclohexanol), 3-tert-부틸-1-사이클로헥산올(3-tert-butyl-1-cyclohexanol), 4-tert-부틸-1-사이클로헥산올(4-tert-butyl-1-cyclohexanol), 2,3-디메틸-1-사이클로헥산올(2,3-dimethyl-1-cyclohexanol), 2,4-디메틸-1-사이클로헥산올(2,4-dimethyl-1-cyclohexanol), 3,4-디메틸-1-사이클로헥산올(3,4-dimethyl-1-cyclohexanol), 1-메틸 사이클로헵탄올(1-methyl cycloheptanol), 2-메틸 사이클로헵탄올(2-methyl cycloheptanol), 3-메틸 사이클로헵탄올(3-mehtyl cycloheptanol) 및 4-메틸 사이클로헵탄올(4-methy cycloheptanol)로 구성되는 군으로부터 선택되는 어느 하나 이상인 것인 폴리알킬렌 카보네이트 수지의 제조방법.
- 제1항에 있어서,상기 화학식 9로 표시되는 화합물은 사이클로부탄올(Cyclobutanol), 사이클로펜탄올(Cyclopentanol), 사이클로헥산올(Cyclohexanol), 사이클로헵탄올 Cycloheptanol), 및 사이클로옥탄올(Cyclooctanol)로 구성되는 군으로부터 선택되는 어느 하나 이상인 것인 폴리알킬렌 카보네이트 수지의 제조방법.
- 제1항에 있어서,상기 이중 금속 시아나이드 화합물은 금속 시아나이드 착염과 금속염으로부터 유래된 것인 폴리알킬렌 카보네이트 수지의 제조방법.
- 제6항에 있어서,상기 금속 시아나이드 착염은 칼륨 헥사시아노코발테이트(Potassium hexacyanocobaltate(Ⅲ)), 칼륨 헥사시아노페레이트(Potassium hexacyanoferrate(Ⅱ)), 칼륨 헥사시아노페레이트(Potassium hexacyanoferrate(Ⅲ)), 칼슘 헥사시아노코발테이트(Calcium hexacyanoferrate(Ⅲ)) 또는 리튬 헥사시아노이리데이트(Lithium hexacyanoiridate(Ⅲ))인 것인 폴리알킬렌 카보네이트 수지의 제조방법.
- 제6항에 있어서,상기 금속염은 염화아연(Ⅱ), 염화아연(Ⅲ), 브롬화아연, 요오드화아연, 아세트산아연, 아연 아세틸아세토네이트, 벤조산아연, 질산아연, 황산철(Ⅱ), 브롬화철(Ⅱ), 염화코발트(Ⅱ), 티오시안산코발트(Ⅱ), 포름산니켈(Ⅱ) 및 질산니켈(Ⅱ)으로 이루어진 군에서 선택된 1종 이상인 것인 폴리알킬렌 카보네이트 수지의 제조방법.
- 제1항에 있어서,상기 촉매는 부착화제를 더 포함하고,상기 부착화제는 말단에 히드록시기, 아민기, 에스테르기, 또는 에테르기를 갖는 화합물인 것인 폴리알킬렌 카보네이트 수지의 제조방법.
- 제1항에 있어서,상기 x는 0.90 내지 0.95이고, y는 0.05 내지 0.10인 것인 폴리알킬렌 카보네이트 수지의 제조방법.
- 제1항에 있어서,상기 화학식 1 및 화학식 2에서, R1 내지 R8은 각각 독립적으로 수소이고,유리전이온도(Tg)가 0℃ 내지 20℃인 것인 폴리알킬렌 카보네이트 수지의 제조방법.
- 제1항에 있어서,상기 화학식 1 및 화학식 2에서, R1 내지 R8은 각각 독립적으로 탄소수 1 내지 20의 선형 알킬기, 탄소수 3 내지 20의 분지형 알킬기, 탄소수 6 내지 20의 아릴기, 탄소수 2 내지 20의 알케닐기, 또는 탄소수 3 내지 20의 사이클로알킬기이고,유리전이온도(Tg)가 30℃ 내지 50℃인 것인 폴리알킬렌 카보네이트 수지의 제조방법.
- 제1항에 있어서,상기 폴리알킬렌 카보네이트 수지 전체 중량에 대하여 고리형 카보네이트의 함량이 0.5 wt% 내지 15.0 wt%인 것인 폴리알킬렌 카보네이트 수지의 제조방법.
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