TW200909473A - Solid state polymerization process for polyester - Google Patents
Solid state polymerization process for polyester Download PDFInfo
- Publication number
- TW200909473A TW200909473A TW097123866A TW97123866A TW200909473A TW 200909473 A TW200909473 A TW 200909473A TW 097123866 A TW097123866 A TW 097123866A TW 97123866 A TW97123866 A TW 97123866A TW 200909473 A TW200909473 A TW 200909473A
- Authority
- TW
- Taiwan
- Prior art keywords
- acid
- bis
- diol
- phosphonic
- polyester
- Prior art date
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- 229920000728 polyester Polymers 0.000 title claims abstract description 70
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 26
- 239000007787 solid Substances 0.000 title claims abstract description 20
- -1 phosphinic acid compound Chemical class 0.000 claims abstract description 68
- 238000000034 method Methods 0.000 claims abstract description 56
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 23
- 150000002009 diols Chemical class 0.000 claims abstract description 19
- 238000005886 esterification reaction Methods 0.000 claims abstract description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 10
- 150000005690 diesters Chemical class 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 25
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 14
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 239000000052 vinegar Substances 0.000 claims description 9
- 235000021419 vinegar Nutrition 0.000 claims description 9
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 claims description 5
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 4
- YQPCHPBGAALCRT-UHFFFAOYSA-N 2-[1-(carboxymethyl)cyclohexyl]acetic acid Chemical compound OC(=O)CC1(CC(O)=O)CCCCC1 YQPCHPBGAALCRT-UHFFFAOYSA-N 0.000 claims description 4
- IEQICHVXWFGDAN-UHFFFAOYSA-N 4-phosphonobenzoic acid Chemical compound OC(=O)C1=CC=C(P(O)(O)=O)C=C1 IEQICHVXWFGDAN-UHFFFAOYSA-N 0.000 claims description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- MQYFWRJEFAZXHE-UHFFFAOYSA-N (2-phenylphenyl)phosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1C1=CC=CC=C1 MQYFWRJEFAZXHE-UHFFFAOYSA-N 0.000 claims description 3
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical group OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 claims description 3
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- UOKRBSXOBUKDGE-UHFFFAOYSA-N butylphosphonic acid Chemical compound CCCCP(O)(O)=O UOKRBSXOBUKDGE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 claims description 3
- PVBGKAMVCZUNFQ-UHFFFAOYSA-N 1-propoxyphosphonoyloxypropane Chemical compound CCCOP(=O)OCCC PVBGKAMVCZUNFQ-UHFFFAOYSA-N 0.000 claims description 2
- WWNZUHFWZPYTBX-UHFFFAOYSA-N 2-phosphonobenzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(P(O)(O)=O)C(C(O)=O)=C1 WWNZUHFWZPYTBX-UHFFFAOYSA-N 0.000 claims description 2
- DQULYJXGTXMNTM-UHFFFAOYSA-N 2-phosphonobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1P(O)(O)=O DQULYJXGTXMNTM-UHFFFAOYSA-N 0.000 claims description 2
- YISPNHJOGNWBMB-UHFFFAOYSA-N 4-phosphonobenzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=C(P(O)(O)=O)C(C(O)=O)=C1C(O)=O YISPNHJOGNWBMB-UHFFFAOYSA-N 0.000 claims description 2
- ZCDDUQKDPBQFMN-UHFFFAOYSA-N 5-phosphonobenzene-1,2,4-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(P(O)(O)=O)C=C1C(O)=O ZCDDUQKDPBQFMN-UHFFFAOYSA-N 0.000 claims description 2
- INJNMXHKFWFNLW-UHFFFAOYSA-N 5-phosphonobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(P(O)(O)=O)=C1 INJNMXHKFWFNLW-UHFFFAOYSA-N 0.000 claims description 2
- FYTSKEXCNMRBEF-UHFFFAOYSA-N C(=O)(O)C1=C(C(=CC(=C1)C(=O)O)C(=O)O)OP(OC1=C(C=C(C=C1C(=O)O)C(=O)O)C(=O)O)=O Chemical compound C(=O)(O)C1=C(C(=CC(=C1)C(=O)O)C(=O)O)OP(OC1=C(C=C(C=C1C(=O)O)C(=O)O)C(=O)O)=O FYTSKEXCNMRBEF-UHFFFAOYSA-N 0.000 claims description 2
- YAGZSFZUIGGOQQ-UHFFFAOYSA-N C(=O)(O)C1=C(C=C(C=C1)C(=O)O)OP(OC1=C(C=CC(=C1)C(=O)O)C(=O)O)=O Chemical compound C(=O)(O)C1=C(C=C(C=C1)C(=O)O)OP(OC1=C(C=CC(=C1)C(=O)O)C(=O)O)=O YAGZSFZUIGGOQQ-UHFFFAOYSA-N 0.000 claims description 2
- RJFXQIMJTDGMSH-UHFFFAOYSA-N C(=O)(O)C1=C(C=CC=C1C(=O)O)OP(OC1=C(C(=CC=C1)C(=O)O)C(=O)O)=O Chemical compound C(=O)(O)C1=C(C=CC=C1C(=O)O)OP(OC1=C(C(=CC=C1)C(=O)O)C(=O)O)=O RJFXQIMJTDGMSH-UHFFFAOYSA-N 0.000 claims description 2
- XTEGAJREDDITNW-UHFFFAOYSA-N C(=O)(O)C1=CC=C(C=C1)OP(OC1=CC=C(C=C1)C(=O)O)=O Chemical compound C(=O)(O)C1=CC=C(C=C1)OP(OC1=CC=C(C=C1)C(=O)O)=O XTEGAJREDDITNW-UHFFFAOYSA-N 0.000 claims description 2
- UBWVLSSOPCGDBX-UHFFFAOYSA-N C(=O)(O)C=1C=C(C=CC1)OP(OC1=CC(=CC=C1)C(=O)O)=O Chemical compound C(=O)(O)C=1C=C(C=CC1)OP(OC1=CC(=CC=C1)C(=O)O)=O UBWVLSSOPCGDBX-UHFFFAOYSA-N 0.000 claims description 2
- URDWQAVIGSVKIQ-UHFFFAOYSA-N C(=O)(O)C=1C=C(C=CC1C(=O)O)OP(OC1=CC(=C(C=C1)C(=O)O)C(=O)O)=O Chemical compound C(=O)(O)C=1C=C(C=CC1C(=O)O)OP(OC1=CC(=C(C=C1)C(=O)O)C(=O)O)=O URDWQAVIGSVKIQ-UHFFFAOYSA-N 0.000 claims description 2
- HZCDANOFLILNSA-UHFFFAOYSA-N Dimethyl hydrogen phosphite Chemical compound COP(=O)OC HZCDANOFLILNSA-UHFFFAOYSA-N 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- BLKXLEPPVDUHBY-UHFFFAOYSA-N bis(propan-2-yl) phosphonate Chemical compound CC(C)OP(=O)OC(C)C BLKXLEPPVDUHBY-UHFFFAOYSA-N 0.000 claims description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- DZQISOJKASMITI-UHFFFAOYSA-N decyl-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound CCCCCCCCCCP(O)(O)=O DZQISOJKASMITI-UHFFFAOYSA-N 0.000 claims description 2
- MJUJXFBTEFXVKU-UHFFFAOYSA-N diethyl phosphonate Chemical compound CCOP(=O)OCC MJUJXFBTEFXVKU-UHFFFAOYSA-N 0.000 claims description 2
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims description 2
- YOOYVODKUBZAPO-UHFFFAOYSA-N naphthalen-1-ylphosphonic acid Chemical compound C1=CC=C2C(P(O)(=O)O)=CC=CC2=C1 YOOYVODKUBZAPO-UHFFFAOYSA-N 0.000 claims description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims description 2
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 claims description 2
- ATLPLEZDTSBZQG-UHFFFAOYSA-N propan-2-ylphosphonic acid Chemical compound CC(C)P(O)(O)=O ATLPLEZDTSBZQG-UHFFFAOYSA-N 0.000 claims description 2
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical group COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- KYLUAQBYONVMCP-UHFFFAOYSA-N (2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P KYLUAQBYONVMCP-UHFFFAOYSA-N 0.000 claims 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims 1
- MNQXFRIDDHPSJP-UHFFFAOYSA-N 2,2,4,4-tetramethylcyclobutan-1-ol Chemical compound CC1(C)CC(C)(C)C1O MNQXFRIDDHPSJP-UHFFFAOYSA-N 0.000 claims 1
- LLCKFEGXYKWRPT-UHFFFAOYSA-N 2-(2-carboxyphenyl)phosphanylbenzoic acid Chemical compound C(=O)(O)C1=C(C=CC=C1)PC1=C(C=CC=C1)C(=O)O LLCKFEGXYKWRPT-UHFFFAOYSA-N 0.000 claims 1
- ICPXIRMAMWRMAD-UHFFFAOYSA-N 2-[3-[2-[3-(2-hydroxyethoxy)phenyl]propan-2-yl]phenoxy]ethanol Chemical compound C=1C=CC(OCCO)=CC=1C(C)(C)C1=CC=CC(OCCO)=C1 ICPXIRMAMWRMAD-UHFFFAOYSA-N 0.000 claims 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 claims 1
- ACOQOLIJGGKILA-UHFFFAOYSA-N 2-methylpentane-1,1-diol Chemical compound CCCC(C)C(O)O ACOQOLIJGGKILA-UHFFFAOYSA-N 0.000 claims 1
- LSGSSTRMKJNXRE-UHFFFAOYSA-N 2-phosphonoterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(P(O)(O)=O)=C1 LSGSSTRMKJNXRE-UHFFFAOYSA-N 0.000 claims 1
- UEDISDQWZXBSKK-UHFFFAOYSA-N 3-[4-[1-[4-(3-hydroxypropoxy)phenyl]ethyl]phenoxy]propan-1-ol Chemical compound C=1C=C(OCCCO)C=CC=1C(C)C1=CC=C(OCCCO)C=C1 UEDISDQWZXBSKK-UHFFFAOYSA-N 0.000 claims 1
- VVIZYFOGYVITMA-UHFFFAOYSA-N 3-phosphanylbenzoic acid Chemical compound OC(=O)c1cccc(P)c1 VVIZYFOGYVITMA-UHFFFAOYSA-N 0.000 claims 1
- TXVJDPRWVLBNQI-UHFFFAOYSA-N 3-phosphonobenzene-1,2,4-tricarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(P(O)(O)=O)=C1C(O)=O TXVJDPRWVLBNQI-UHFFFAOYSA-N 0.000 claims 1
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 claims 1
- DTXOHBIZJVBVRX-UHFFFAOYSA-N C(=O)(O)C1=C(C(=CC=C1C(=O)O)C(=O)O)OP(OC1=C(C(=CC=C1C(=O)O)C(=O)O)C(=O)O)=O Chemical compound C(=O)(O)C1=C(C(=CC=C1C(=O)O)C(=O)O)OP(OC1=C(C(=CC=C1C(=O)O)C(=O)O)C(=O)O)=O DTXOHBIZJVBVRX-UHFFFAOYSA-N 0.000 claims 1
- RUTZSNXEJBHPEE-UHFFFAOYSA-N C(=O)(O)C1=C(C=C(C(=C1)C(=O)O)C(=O)O)OP(OC1=C(C=C(C(=C1)C(=O)O)C(=O)O)C(=O)O)=O Chemical compound C(=O)(O)C1=C(C=C(C(=C1)C(=O)O)C(=O)O)OP(OC1=C(C=C(C(=C1)C(=O)O)C(=O)O)C(=O)O)=O RUTZSNXEJBHPEE-UHFFFAOYSA-N 0.000 claims 1
- WVNLRMSTXQBZOB-UHFFFAOYSA-N C(=O)(O)C1=C(C=C(C=C1C(=O)O)C(=O)O)OP(OC1=C(C(=CC(=C1)C(=O)O)C(=O)O)C(=O)O)=O Chemical compound C(=O)(O)C1=C(C=C(C=C1C(=O)O)C(=O)O)OP(OC1=C(C(=CC(=C1)C(=O)O)C(=O)O)C(=O)O)=O WVNLRMSTXQBZOB-UHFFFAOYSA-N 0.000 claims 1
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- BSPFQSHOYKMNMN-UHFFFAOYSA-N C(=O)(O)C=1C=C(C=C(C1)C(=O)O)OP(OC1=CC(=CC(=C1)C(=O)O)C(=O)O)=O Chemical compound C(=O)(O)C=1C=C(C=C(C1)C(=O)O)OP(OC1=CC(=CC(=C1)C(=O)O)C(=O)O)=O BSPFQSHOYKMNMN-UHFFFAOYSA-N 0.000 claims 1
- RQLSQSAHOLKGEM-UHFFFAOYSA-N C1=CC(=C(C(=C1C(=O)O)C(=O)O)C(=O)O)PC2=C(C(=C(C=C2)C(=O)O)C(=O)O)C(=O)O Chemical compound C1=CC(=C(C(=C1C(=O)O)C(=O)O)C(=O)O)PC2=C(C(=C(C=C2)C(=O)O)C(=O)O)C(=O)O RQLSQSAHOLKGEM-UHFFFAOYSA-N 0.000 claims 1
- OSZNJFBDDYGWHW-UHFFFAOYSA-N C1=CC(=C(C=C1C(=O)O)C(=O)O)PC2=C(C=C(C=C2)C(=O)O)C(=O)O Chemical compound C1=CC(=C(C=C1C(=O)O)C(=O)O)PC2=C(C=C(C=C2)C(=O)O)C(=O)O OSZNJFBDDYGWHW-UHFFFAOYSA-N 0.000 claims 1
- 239000001263 FEMA 3042 Substances 0.000 claims 1
- GTMHMIHIJDBGRG-UHFFFAOYSA-N P(O)(O)=O.C(=O)(O)C=1C=CC=C(C1)C(=O)O Chemical compound P(O)(O)=O.C(=O)(O)C=1C=CC=C(C1)C(=O)O GTMHMIHIJDBGRG-UHFFFAOYSA-N 0.000 claims 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims 1
- DKOUXNIAYKMRFD-UHFFFAOYSA-N [O-2].C(C)C(C[Ti+3])CCCC.[O-2].[O-2].C(C)C(C[Ti+3])CCCC Chemical compound [O-2].C(C)C(C[Ti+3])CCCC.[O-2].[O-2].C(C)C(C[Ti+3])CCCC DKOUXNIAYKMRFD-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- PTLIZOFGXLGHSY-UHFFFAOYSA-N dibutylphosphane Chemical compound CCCCPCCCC PTLIZOFGXLGHSY-UHFFFAOYSA-N 0.000 claims 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 claims 1
- 229960001826 dimethylphthalate Drugs 0.000 claims 1
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- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 125000004424 polypyridyl Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/80—Solid-state polycondensation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/87—Non-metals or inter-compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
Landscapes
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93750907P | 2007-06-28 | 2007-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200909473A true TW200909473A (en) | 2009-03-01 |
Family
ID=39717636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097123866A TW200909473A (en) | 2007-06-28 | 2008-06-26 | Solid state polymerization process for polyester |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20090005531A1 (OSRAM) |
| EP (1) | EP2158252A1 (OSRAM) |
| JP (1) | JP2010531373A (OSRAM) |
| CN (1) | CN101687984A (OSRAM) |
| TW (1) | TW200909473A (OSRAM) |
| WO (1) | WO2009000708A1 (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2268699B1 (en) | 2008-04-03 | 2011-09-28 | Basf Se | Solid state polymerization process for polyester with phosphinic acid compounds |
| US8404878B2 (en) * | 2010-04-07 | 2013-03-26 | American Air Liquide, Inc. | Titanium-containing precursors for vapor deposition |
| WO2012071187A1 (en) | 2010-11-22 | 2012-05-31 | E. I. Du Pont De Nemours And Company | Improved solid state polymerizations of polyester elastomers |
| WO2013062408A1 (en) * | 2011-10-24 | 2013-05-02 | Furanix Technologies B.V. | A process for preparing a polymer product having a 2,5-furandicarboxylate moiety within the polymer backbone to be used in bottle, film or fibre applications |
| CN103193635B (zh) * | 2013-04-08 | 2015-06-03 | 南通大学 | 一种抗氧剂二[3-(3,5-二叔丁基-4-羟基苯基)]丙酸丁二醇酯的制备方法 |
| WO2015137805A1 (en) * | 2014-03-11 | 2015-09-17 | Furanix Technologies B.V. | Polyester and method for preparing such a polyester |
| EP3000835B1 (en) * | 2014-09-24 | 2020-11-25 | Clariant International Ltd | Catalyst composition for a polyester manufacturing process |
| CN104725616B (zh) * | 2015-04-13 | 2017-01-11 | 南京大学 | 有机胍催化熔融-固相缩聚合成聚(己二酸-共-对苯二甲酸丁二醇酯) |
| CN107513154B (zh) * | 2017-09-14 | 2020-08-21 | 江苏景宏新材料科技有限公司 | 一种钛系聚酯催化剂及其生产共聚酯的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5453479A (en) * | 1993-07-12 | 1995-09-26 | General Electric Company | Polyesterification catalyst |
| DE19518943C2 (de) * | 1995-05-23 | 1999-12-09 | Inventa Fischer Gmbh | Verfahren zur Herstellung von Polyestern unter Verwendung von titanhaltigen Katalysator-Inhibitor-Kombinationen |
| US5981690A (en) * | 1998-04-17 | 1999-11-09 | E. I. Du Pont De Nemours And Company | Poly(alkylene arylates) having improved optical properties |
| MXPA03007914A (es) * | 2001-03-28 | 2003-12-11 | Ciba Sc Holding Ag | Proceso para preparar un poliester estabilizado. |
| TWI302154B (OSRAM) * | 2001-07-05 | 2008-10-21 | Teijin Ltd | |
| EP1550683B1 (en) * | 2002-10-03 | 2017-04-26 | Toray Industries, Inc. | Polyester resin compositions, polyester film, and magnetic recording medium |
| KR20070039494A (ko) * | 2004-07-20 | 2007-04-12 | 솔로텍스 가부시끼가이샤 | 폴리트리메틸렌 테레프탈레이트 |
| WO2007017931A1 (ja) * | 2005-08-09 | 2007-02-15 | Toyo Boseki Kabushiki Kaisha | ポリエステル樹脂およびそれからなるポリエステル樹脂組成物並びにその用途 |
| JPWO2007032325A1 (ja) * | 2005-09-14 | 2009-03-19 | 東洋紡績株式会社 | ポリエステルおよびポリエステルの製造方法、ならびにポリエステル成形体 |
| US7932345B2 (en) * | 2005-09-16 | 2011-04-26 | Grupo Petrotemex, S.A. De C.V. | Aluminum containing polyester polymers having low acetaldehyde generation rates |
-
2008
- 2008-06-18 EP EP08802922A patent/EP2158252A1/en not_active Withdrawn
- 2008-06-18 JP JP2010513850A patent/JP2010531373A/ja not_active Withdrawn
- 2008-06-18 WO PCT/EP2008/057640 patent/WO2009000708A1/en not_active Ceased
- 2008-06-18 CN CN200880022488A patent/CN101687984A/zh active Pending
- 2008-06-26 TW TW097123866A patent/TW200909473A/zh unknown
- 2008-06-26 US US12/215,277 patent/US20090005531A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009000708A1 (en) | 2008-12-31 |
| US20090005531A1 (en) | 2009-01-01 |
| JP2010531373A (ja) | 2010-09-24 |
| CN101687984A (zh) | 2010-03-31 |
| EP2158252A1 (en) | 2010-03-03 |
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