JPH0141651B2 - - Google Patents
Info
- Publication number
- JPH0141651B2 JPH0141651B2 JP483581A JP483581A JPH0141651B2 JP H0141651 B2 JPH0141651 B2 JP H0141651B2 JP 483581 A JP483581 A JP 483581A JP 483581 A JP483581 A JP 483581A JP H0141651 B2 JPH0141651 B2 JP H0141651B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- polyester
- mol
- sulfonic acid
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 29
- 229920000728 polyester Polymers 0.000 claims description 27
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 18
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- -1 polyethylene terephthalate Polymers 0.000 description 20
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- 238000005886 esterification reaction Methods 0.000 description 10
- 238000006068 polycondensation reaction Methods 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000007086 side reaction Methods 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000037048 polymerization activity Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- ORQOVDIGLUWNIH-UHFFFAOYSA-N 4-ethoxycarbonylbenzenesulfonic acid Chemical compound CCOC(=O)C1=CC=C(S(O)(=O)=O)C=C1 ORQOVDIGLUWNIH-UHFFFAOYSA-N 0.000 description 1
- ADFVYWCDAKWKPH-UHFFFAOYSA-N 4-ethoxycarbonylbenzoic acid Chemical compound CCOC(=O)C1=CC=C(C(O)=O)C=C1 ADFVYWCDAKWKPH-UHFFFAOYSA-N 0.000 description 1
- XZTNYUNDTCLYKX-UHFFFAOYSA-N 4-methoxycarbonyl-3-nitrobenzenesulfonic acid Chemical compound COC(=O)C1=CC=C(S(O)(=O)=O)C=C1[N+]([O-])=O XZTNYUNDTCLYKX-UHFFFAOYSA-N 0.000 description 1
- VLXWTIUMKPVDON-UHFFFAOYSA-N 4-methoxycarbonylbenzenesulfonic acid Chemical compound COC(=O)C1=CC=C(S(O)(=O)=O)C=C1 VLXWTIUMKPVDON-UHFFFAOYSA-N 0.000 description 1
- WNKQDGLSQUASME-UHFFFAOYSA-N 4-sulfophthalic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1C(O)=O WNKQDGLSQUASME-UHFFFAOYSA-N 0.000 description 1
- HOPNOJQHZDOAPO-UHFFFAOYSA-N C(C)OS(=O)(=O)C1=CC=C(C=C1)I Chemical compound C(C)OS(=O)(=O)C1=CC=C(C=C1)I HOPNOJQHZDOAPO-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KNVLCWQKYHCADB-UHFFFAOYSA-N chlorosulfonyloxymethane Chemical compound COS(Cl)(=O)=O KNVLCWQKYHCADB-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- XCEDLSQLKUOFPM-UHFFFAOYSA-N diethyl ethane-1,2-disulfonate Chemical compound CCOS(=O)(=O)CCS(=O)(=O)OCC XCEDLSQLKUOFPM-UHFFFAOYSA-N 0.000 description 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- XDRMBCMMABGNMM-UHFFFAOYSA-N ethyl benzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=CC=C1 XDRMBCMMABGNMM-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- ANNNGOUEZBONHD-UHFFFAOYSA-N ethyl phenylmethanesulfonate Chemical compound CCOS(=O)(=O)CC1=CC=CC=C1 ANNNGOUEZBONHD-UHFFFAOYSA-N 0.000 description 1
- DOUJUESPGUUHMX-UHFFFAOYSA-N ethyl quinoline-8-sulfonate Chemical compound C1=CN=C2C(S(=O)(=O)OCC)=CC=CC2=C1 DOUJUESPGUUHMX-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- RXHIZFMFPLHZDT-UHFFFAOYSA-N hexadecyl 4-methylbenzenesulfonate Chemical compound CCCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=C(C)C=C1 RXHIZFMFPLHZDT-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- NHFXFWUOYKCKBC-UHFFFAOYSA-N methoxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound COS(=O)(=S)C1=CC=C(C)C=C1 NHFXFWUOYKCKBC-UHFFFAOYSA-N 0.000 description 1
- RNQAAVNGCJFEJE-UHFFFAOYSA-N methyl 4-(dimethylamino)benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(N(C)C)C=C1 RNQAAVNGCJFEJE-UHFFFAOYSA-N 0.000 description 1
- VQFKYAZZFFNYQV-UHFFFAOYSA-N methyl 4-chlorobenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(Cl)C=C1 VQFKYAZZFFNYQV-UHFFFAOYSA-N 0.000 description 1
- IQEHSUZNQISVKO-UHFFFAOYSA-N methyl 4-methoxybenzenesulfonate Chemical compound COC1=CC=C(S(=O)(=O)OC)C=C1 IQEHSUZNQISVKO-UHFFFAOYSA-N 0.000 description 1
- WEIPRCBTQPXBTJ-UHFFFAOYSA-N methyl 4-sulfanylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(S)C=C1 WEIPRCBTQPXBTJ-UHFFFAOYSA-N 0.000 description 1
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP483581A JPS57119924A (en) | 1981-01-16 | 1981-01-16 | Manufacture of polyester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP483581A JPS57119924A (en) | 1981-01-16 | 1981-01-16 | Manufacture of polyester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57119924A JPS57119924A (en) | 1982-07-26 |
| JPH0141651B2 true JPH0141651B2 (enrdf_load_stackoverflow) | 1989-09-06 |
Family
ID=11594743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP483581A Granted JPS57119924A (en) | 1981-01-16 | 1981-01-16 | Manufacture of polyester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57119924A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117069626A (zh) * | 2023-10-18 | 2023-11-17 | 上海帼帆化工新材料有限公司 | 反应型抗菌组分、其合成方法以及在制备抗菌聚酯中的应用 |
-
1981
- 1981-01-16 JP JP483581A patent/JPS57119924A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57119924A (en) | 1982-07-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4501878A (en) | Process for the preparation of high molecular weight polyesters | |
| KR100459654B1 (ko) | 1,4-사이클로헥산디메탄올이 공중합된 폴리에스테르수지의 제조방법 | |
| TWI618730B (zh) | 聚酯樹脂的製備方法 | |
| EP1384740A1 (en) | Process for preparing copolyesters of terephthalic acid, ethylene glycol, and 1,4-cyclohexanedimethanol exhibiting a neutral hue, high clarity and increased brightness | |
| US4131601A (en) | Process for the preparation of polyesters | |
| EP2371875A2 (en) | Method for preparing a polyester resin in which isosorbide is copolymerized | |
| US5898060A (en) | Copolyester for molding a bottle | |
| JPS60147430A (ja) | 高白度，高重合度アジピン酸共重合ポリエステルの製造法 | |
| JPH0141651B2 (enrdf_load_stackoverflow) | ||
| JP3108047B2 (ja) | ポリエステル樹脂の製造方法 | |
| EP0119731B1 (en) | Copolyester of polyethylene terephthalate, process for making it and its use in producing molded articles | |
| JPS6364449B2 (enrdf_load_stackoverflow) | ||
| JPS6333489B2 (enrdf_load_stackoverflow) | ||
| US4547563A (en) | Copolyester of polyethylene terephthalate and bis (4-beta hydroxy ethoxy phenyl) sulfone | |
| JPS591416B2 (ja) | ポリエステルの製造方法 | |
| JP2002030137A (ja) | 改質ポリエステルの製造方法 | |
| JPS5838722A (ja) | ポリエステルの製造方法 | |
| JPS6136777B2 (enrdf_load_stackoverflow) | ||
| JPS6159335B2 (enrdf_load_stackoverflow) | ||
| KR950006132B1 (ko) | 폴리에스테르의 제조방법 | |
| JPS60250028A (ja) | ポリエステルの製造法 | |
| JPH0150250B2 (enrdf_load_stackoverflow) | ||
| JPH026769B2 (enrdf_load_stackoverflow) | ||
| JPS6254130B2 (enrdf_load_stackoverflow) | ||
| KR0122004B1 (ko) | 폴리에스테르의 제조방법 |