CA1139493A - Method for the production of a high molecular weight polyester prepared from a prepolymer polyester having an optimal carboxyl content - Google Patents
Method for the production of a high molecular weight polyester prepared from a prepolymer polyester having an optimal carboxyl contentInfo
- Publication number
- CA1139493A CA1139493A CA000350040A CA350040A CA1139493A CA 1139493 A CA1139493 A CA 1139493A CA 000350040 A CA000350040 A CA 000350040A CA 350040 A CA350040 A CA 350040A CA 1139493 A CA1139493 A CA 1139493A
- Authority
- CA
- Canada
- Prior art keywords
- stage
- dicarboxylic
- glycol
- reaction
- polyester
- 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
- 229920000728 polyester Polymers 0.000 title claims abstract description 116
- 238000000034 method Methods 0.000 title claims abstract description 70
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title claims abstract description 62
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 53
- 239000007787 solid Substances 0.000 claims abstract description 49
- 230000008569 process Effects 0.000 claims abstract description 36
- 230000003068 static effect Effects 0.000 claims abstract description 24
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 157
- 238000006243 chemical reaction Methods 0.000 claims description 89
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 68
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 65
- 238000005886 esterification reaction Methods 0.000 claims description 48
- 150000002148 esters Chemical class 0.000 claims description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 230000032050 esterification Effects 0.000 claims description 42
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 36
- 239000002245 particle Substances 0.000 claims description 29
- 238000006068 polycondensation reaction Methods 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 23
- -1 alkyl dicarboxylic acids Chemical class 0.000 claims description 19
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 16
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 14
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 14
- 239000000047 product Substances 0.000 claims description 13
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 12
- 239000012159 carrier gas Substances 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 11
- 150000002334 glycols Chemical class 0.000 claims description 11
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 9
- RYRZSXJVEILFRR-UHFFFAOYSA-N 2,3-dimethylterephthalic acid Chemical compound CC1=C(C)C(C(O)=O)=CC=C1C(O)=O RYRZSXJVEILFRR-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims description 7
- 229910052786 argon Inorganic materials 0.000 claims description 7
- 239000001307 helium Substances 0.000 claims description 7
- 229910052734 helium Inorganic materials 0.000 claims description 7
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 7
- 239000012535 impurity Substances 0.000 claims description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052753 mercury Inorganic materials 0.000 claims description 6
- 230000008859 change Effects 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims 13
- 238000002360 preparation method Methods 0.000 claims 7
- 239000003570 air Substances 0.000 claims 3
- 238000005755 formation reaction Methods 0.000 claims 3
- 229940000425 combination drug Drugs 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 23
- 239000006227 byproduct Substances 0.000 abstract description 19
- 229920000642 polymer Polymers 0.000 abstract description 8
- 239000000155 melt Substances 0.000 abstract description 7
- 230000002939 deleterious effect Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract 1
- 230000007246 mechanism Effects 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 9
- 238000009792 diffusion process Methods 0.000 description 9
- 238000005809 transesterification reaction Methods 0.000 description 8
- 239000010936 titanium Substances 0.000 description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052787 antimony Inorganic materials 0.000 description 4
- 230000003750 conditioning effect Effects 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 3
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 3
- 230000036647 reaction Effects 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229960001826 dimethylphthalate Drugs 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052758 niobium Inorganic materials 0.000 description 2
- 239000010955 niobium Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229940083957 1,2-butanediol Drugs 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- IYZRGMOLITUAPC-UHFFFAOYSA-N 2,3-diethylnaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(CC)C(CC)=CC2=C1 IYZRGMOLITUAPC-UHFFFAOYSA-N 0.000 description 1
- VQENMVNDKOIXBZ-UHFFFAOYSA-N 2,5-dimethylnaphthalene-1-carboxylic acid Chemical compound CC1=CC=CC2=C(C(O)=O)C(C)=CC=C21 VQENMVNDKOIXBZ-UHFFFAOYSA-N 0.000 description 1
- IWEATXLWFWACOA-UHFFFAOYSA-N 2,6-dimethylnaphthalene-1-carboxylic acid Chemical compound OC(=O)C1=C(C)C=CC2=CC(C)=CC=C21 IWEATXLWFWACOA-UHFFFAOYSA-N 0.000 description 1
- SDAMTPCXBPNEQC-UHFFFAOYSA-N 3,4-dimethylphthalic acid Chemical compound CC1=CC=C(C(O)=O)C(C(O)=O)=C1C SDAMTPCXBPNEQC-UHFFFAOYSA-N 0.000 description 1
- HAYIPGIFANTODX-UHFFFAOYSA-N 4,6-dimethylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC(C)=C(C(O)=O)C=C1C(O)=O HAYIPGIFANTODX-UHFFFAOYSA-N 0.000 description 1
- NKLQILGKAICSCT-UHFFFAOYSA-N C(C)C1=CC(=C(C=C1C(=O)O)C(=O)O)CC Chemical compound C(C)C1=CC(=C(C=C1C(=O)O)C(=O)O)CC NKLQILGKAICSCT-UHFFFAOYSA-N 0.000 description 1
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
- 241000270878 Hyla Species 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- OBGTVKSPZYNOIS-UHFFFAOYSA-N dimethyl benzene-1,2-dicarboxylate 2,3-dimethylterephthalic acid Chemical class CC=1C(=C(C(=O)O)C=CC1C(=O)O)C.COC(C=1C(C(=O)OC)=CC=CC1)=O OBGTVKSPZYNOIS-UHFFFAOYSA-N 0.000 description 1
- OVPXRLUTUWRYEY-UHFFFAOYSA-N dimethyl naphthalene-1,8-dicarboxylate Chemical class C1=CC(C(=O)OC)=C2C(C(=O)OC)=CC=CC2=C1 OVPXRLUTUWRYEY-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 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
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 238000010671 solid-state reaction Methods 0.000 description 1
- 239000004753 textile Substances 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
-
- 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
- C08G63/02—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
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47,849 | 1979-06-12 | ||
| US90/001508A US4238593B1 (en) | 1979-06-12 | 1979-06-12 | Method for production of a high molecular weight polyester prepared from a prepolymer polyester having an optional carboxyl content |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1139493A true CA1139493A (en) | 1983-01-11 |
Family
ID=21951339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000350040A Expired CA1139493A (en) | 1979-06-12 | 1980-04-17 | Method for the production of a high molecular weight polyester prepared from a prepolymer polyester having an optimal carboxyl content |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4238593B1 (enExample) |
| JP (1) | JPS562321A (enExample) |
| KR (1) | KR840000282B1 (enExample) |
| AU (1) | AU532816B2 (enExample) |
| BE (1) | BE883799A (enExample) |
| BR (1) | BR8003311A (enExample) |
| CA (1) | CA1139493A (enExample) |
| DE (1) | DE3022076A1 (enExample) |
| FR (1) | FR2465759A1 (enExample) |
| GB (1) | GB2051100B (enExample) |
| IT (1) | IT1128160B (enExample) |
| MX (1) | MX156234A (enExample) |
Families Citing this family (99)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0032163B1 (de) * | 1979-12-21 | 1986-01-08 | Hüls Aktiengesellschaft | Verfahren zum Regenerieren und Aufarbeiten von inaktivem linearen Poly(alkylenterephthalat) |
| US4387213A (en) * | 1979-12-21 | 1983-06-07 | Chemische Werke Huels Ag | Process for the condensation of linear polyalkylene terephthalates |
| JPS5830703A (ja) * | 1981-08-17 | 1983-02-23 | Sumitomo Electric Ind Ltd | シリコン樹脂クラツド光通信用フアイバ |
| US4357461A (en) * | 1981-12-11 | 1982-11-02 | Owens-Illinois, Inc. | Polyester stabilization and composition |
| JPS59140222A (ja) * | 1983-01-31 | 1984-08-11 | Teijin Ltd | カルボキシル基末端濃度の大なる芳香族ポリエステル及びその製造法 |
| JPS59219328A (ja) * | 1983-05-28 | 1984-12-10 | Toyobo Co Ltd | 高重合度ポリエステルの製造方法 |
| JPS62174225A (ja) * | 1986-01-28 | 1987-07-31 | Kanebo Ltd | 中空成形用ポリエステル及びその製造方法 |
| US5408035A (en) * | 1991-10-16 | 1995-04-18 | Shell Oil Company | Solid state polymerization |
| JP3024030B2 (ja) * | 1992-12-07 | 2000-03-21 | ポリプラスチックス株式会社 | 加水分解安定性の優れたポリブチレンテレフタレート重合体の製造方法 |
| US5539078A (en) | 1994-12-14 | 1996-07-23 | Shell Oil Company | Process for manufacturing polyester copolymers |
| TW354305B (en) * | 1994-12-22 | 1999-03-11 | Eastman Chem Co | Production of particular polyesters using a novel catalyst system |
| JP3407450B2 (ja) | 1995-01-11 | 2003-05-19 | 三菱化学株式会社 | ダイレクトブローボトル成形用高粘度ポリエステルの製造方法 |
| DE19503054B4 (de) * | 1995-02-01 | 2005-12-22 | Zimmer Ag | Verfahren zur thermischen Behandlung von Polyestergranulat in fester Phase |
| DE19503053B4 (de) * | 1995-02-01 | 2005-08-18 | Zimmer Ag | Verfahren zur direkten Herstellung von Polyester-Verpackungen |
| AU6026996A (en) * | 1995-06-06 | 1996-12-24 | University Of North Carolina At Chapel Hill, The | Process for the preparation of polyester in carbon dioxide |
| US5962557A (en) * | 1996-09-30 | 1999-10-05 | Eastman Chemical Corporation | Polyesters containing copolymerized substituted 1,4-bis(2,6-dialkylanilino)-9, 10-anthraquinones as colorants |
| KR19980061618A (ko) * | 1996-12-31 | 1998-10-07 | 김준웅 | 고중합도 폴리트리메틸렌테레프탈레이트의 제조방법 |
| US6288202B1 (en) | 1997-04-11 | 2001-09-11 | The University Of North Carolina At Chapel Hill | Synthesis of polycarbonates using Co2 |
| US6048957A (en) * | 1997-05-01 | 2000-04-11 | Eastman Chemical Company | Process for polyesters with improved properties |
| DE19814529A1 (de) | 1998-04-01 | 1999-10-07 | Basf Ag | Polyalkylenarylate mit hohem Carbonylendgruppengehalt |
| US6376642B1 (en) | 1998-07-07 | 2002-04-23 | Atofina Chemicals, Inc. | Polyester polycondensation with lithium titanyl oxalate catalyst |
| AU1370800A (en) | 1999-02-04 | 2000-08-25 | Buhler Ag | Process for upgrading plastic material |
| US6183848B1 (en) | 1999-06-03 | 2001-02-06 | Eastman Chemical Company | Low melt viscosity amorphous copolyesters with enhanced glass transition temperatures having improved gas barrier properties |
| US6287656B1 (en) | 1999-06-03 | 2001-09-11 | Eastman Chemical Corporation | Low melt viscosity amorphous copolyesters having improved resistance to lipids |
| US6120889A (en) * | 1999-06-03 | 2000-09-19 | Eastman Chemical Company | Low melt viscosity amorphous copolyesters with enhanced glass transition temperatures |
| US6384180B1 (en) | 1999-08-24 | 2002-05-07 | Eastman Chemical Company | Method for making polyesters employing acidic phosphorus-containing compounds |
| US6258925B1 (en) | 2000-01-07 | 2001-07-10 | Atofina Chemicals, Inc. | Polyester polycondensation with titanyl oxalate catalyst and a catalyst enhancer |
| US6372879B1 (en) | 2000-01-07 | 2002-04-16 | Atofina Chemicals, Inc. | Polyester polycondensation with catalyst and a catalyst enhancer |
| US6472500B2 (en) * | 2000-06-17 | 2002-10-29 | General Electric Company | Crystalline polyester resins and processes for their preparation |
| US6342578B1 (en) | 2000-12-06 | 2002-01-29 | Arteva North America S.A.R.L. | Copolyester with high carboxyl end groups and a method for making |
| PT2311897E (pt) | 2000-12-07 | 2015-08-25 | Grupo Petrotemex Sa De Cv | Processo de preparação de poliéster de baixo custo utilizando um reator tubular |
| US6906164B2 (en) | 2000-12-07 | 2005-06-14 | Eastman Chemical Company | Polyester process using a pipe reactor |
| US6716898B2 (en) | 2001-05-18 | 2004-04-06 | Eastman Chemical Company | Amber polyester compositions for packaging food and beverages |
| KR100446474B1 (ko) * | 2001-05-30 | 2004-09-01 | 주식회사 삼양사 | 내구성이 우수한 폴리부틸렌테레프탈레이트 수지의 제조방법 |
| DE10132928A1 (de) * | 2001-07-03 | 2003-01-16 | Buehler Ag | Modifizierte nachkondensierte Polyester |
| US20030060596A1 (en) * | 2001-07-18 | 2003-03-27 | Turner Sam Richard | Amorphous copolyesters |
| US7834127B2 (en) * | 2001-07-18 | 2010-11-16 | Eastman Chemical Company | Amorphous copolyesters |
| US6713641B2 (en) * | 2001-10-19 | 2004-03-30 | Eastman Chemical Company | Reactive anthraquinone colorant compounds and polymeric materials reacted therewith |
| EP1475402B1 (en) * | 2002-02-14 | 2009-06-24 | Mitsui Chemicals, Inc. | Polyester resin and catalyst for polyester production, process for producing polyester resin with the catalyst |
| US6787589B2 (en) * | 2002-10-31 | 2004-09-07 | Eastman Chemical Company | Amber polyester compositions and container articles produced therefrom |
| US6914120B2 (en) * | 2002-11-13 | 2005-07-05 | Eastman Chemical Company | Method for making isosorbide containing polyesters |
| US6896966B2 (en) * | 2002-11-22 | 2005-05-24 | Eastman Chemical Company | Articles of manufacture incorporating polyester/polycarbonate blends |
| US7118799B2 (en) * | 2002-11-22 | 2006-10-10 | Eastman Chemical Company | Thermoplastic article having a decorative material embedded therein |
| US7297735B2 (en) * | 2003-03-05 | 2007-11-20 | Eastman Chemical Company | Polycarbonate compositions |
| US20040143041A1 (en) * | 2003-01-13 | 2004-07-22 | Pearson Jason Clay | Polyester compositions |
| US7482397B2 (en) * | 2003-01-13 | 2009-01-27 | Eastman Chemical Company | Polycarbonate compositions |
| US20040151854A1 (en) * | 2003-02-03 | 2004-08-05 | Pecorini Thomas Joseph | Extrusion blow molded articles |
| US7338992B2 (en) * | 2003-03-05 | 2008-03-04 | Eastman Chemical Company | Polyolefin compositions |
| EP1599532B1 (en) * | 2003-03-05 | 2017-05-17 | Eastman Chemical Company | Polymer compositions containing an ultraviolet light absorbing compound |
| US20040180994A1 (en) * | 2003-03-05 | 2004-09-16 | Pearson Jason Clay | Polyolefin compositions |
| US20040192813A1 (en) * | 2003-03-20 | 2004-09-30 | Pearson Jason Clay | Polymer compositions containing an ultraviolet light absorbing compound |
| DE60320035T2 (de) * | 2003-03-05 | 2009-05-14 | Eastman Chemical Co., Kingsport | Polymerblends |
| US20050277771A1 (en) * | 2003-03-20 | 2005-12-15 | Pearson Jason C | Process for the preparation of a hindered amine light stabilizer salt |
| US7074879B2 (en) | 2003-06-06 | 2006-07-11 | Eastman Chemical Company | Polyester process using a pipe reactor |
| US7135541B2 (en) * | 2003-06-06 | 2006-11-14 | Eastman Chemical Company | Polyester process using a pipe reactor |
| US20050054757A1 (en) * | 2003-09-10 | 2005-03-10 | Pearson Jason Clay | Method for reducing the acetaldehyde level in polyesters |
| US20050187374A1 (en) * | 2004-02-20 | 2005-08-25 | Bin Chen | Polyester synthesis with enhanced titanium catalyst composition |
| US7332548B2 (en) | 2004-03-04 | 2008-02-19 | Eastman Chemical Company | Process for production of a polyester product from alkylene oxide and carboxylic acid |
| DE102004010680A1 (de) | 2004-03-04 | 2005-10-06 | Zimmer Ag | Verfahren zur Herstellung von hochkondensierten Polyestern in der festen Phase |
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| WO2007052294A2 (en) * | 2005-08-22 | 2007-05-10 | Reliance Industries Ltd. | An improved process for the production of slow crystallizing polyester resin |
| US20080207868A1 (en) * | 2005-09-01 | 2008-08-28 | Mitsubish Chemical Corporation | Apparatus for Heat Treatment of Polyester Particle and Method of Multistage Solid-Phase Polycondensation of Polyester Particle |
| US7655746B2 (en) | 2005-09-16 | 2010-02-02 | Eastman Chemical Company | Phosphorus containing compounds for reducing acetaldehyde in polyesters polymers |
| DE102006012587B4 (de) * | 2006-03-16 | 2015-10-29 | Lurgi Zimmer Gmbh | Verfahren und Vorrichtung zur Kristallisation von Polyestermaterial |
| US7211634B1 (en) | 2006-04-28 | 2007-05-01 | Eastman Chemical Company | Process for the preparation of polyesters containing 1,4-cyclohexanedimethanol |
| TW200813119A (en) * | 2006-08-02 | 2008-03-16 | Mitsubishi Chem Corp | Polyester resin particle and method for producing the same |
| US20080085390A1 (en) | 2006-10-04 | 2008-04-10 | Ryan Thomas Neill | Encapsulation of electrically energized articles |
| US8287991B2 (en) | 2006-10-04 | 2012-10-16 | Eastman Chemical Company | Using branched polymers to control the dimensional stability of articles in the lamination process |
| US7943094B2 (en) | 2006-12-07 | 2011-05-17 | Grupo Petrotemex, S.A. De C.V. | Polyester production system employing horizontally elongated esterification vessel |
| US7649109B2 (en) | 2006-12-07 | 2010-01-19 | Eastman Chemical Company | Polyester production system employing recirculation of hot alcohol to esterification zone |
| US20080167440A1 (en) * | 2007-01-10 | 2008-07-10 | Pickel Deanna L | Use of copolymerizable sulfonate salts to promote char formation in polyesters and copolyesters |
| US7863477B2 (en) | 2007-03-08 | 2011-01-04 | Eastman Chemical Company | Polyester production system employing hot paste to esterification zone |
| US7847053B2 (en) | 2007-07-12 | 2010-12-07 | Eastman Chemical Company | Multi-level tubular reactor with oppositely extending segments |
| US7868129B2 (en) | 2007-07-12 | 2011-01-11 | Eastman Chemical Company | Sloped tubular reactor with spaced sequential trays |
| US7842777B2 (en) | 2007-07-12 | 2010-11-30 | Eastman Chemical Company | Sloped tubular reactor with divided flow |
| US7868130B2 (en) | 2007-07-12 | 2011-01-11 | Eastman Chemical Company | Multi-level tubular reactor with vertically spaced segments |
| US7829653B2 (en) | 2007-07-12 | 2010-11-09 | Eastman Chemical Company | Horizontal trayed reactor |
| US7858730B2 (en) | 2007-07-12 | 2010-12-28 | Eastman Chemical Company | Multi-level tubular reactor with dual headers |
| US7872090B2 (en) | 2007-07-12 | 2011-01-18 | Eastman Chemical Company | Reactor system with optimized heating and phase separation |
| US7872089B2 (en) | 2007-07-12 | 2011-01-18 | Eastman Chemical Company | Multi-level tubular reactor with internal tray |
| US9074092B2 (en) | 2010-12-20 | 2015-07-07 | Eastman Chemical Company | Miscible polyester blends utilizing recycled polyesters |
| JP5678667B2 (ja) * | 2011-01-05 | 2015-03-04 | 三菱化学株式会社 | 脂肪族ポリエステルの製造方法 |
| US9150006B2 (en) | 2011-06-23 | 2015-10-06 | Eastman Chemical Company | Lamination process optimization utilizing neopentyl glycol-modified polyesters |
| DE102011089056A1 (de) * | 2011-12-19 | 2013-06-20 | Evonik Industries Ag | Verfahren zur Herstellung von Polyestern |
| US9517584B2 (en) | 2013-12-18 | 2016-12-13 | Eastman Chemical Company | Articles comprising isosorbide and processes for their manufacture |
| US10590235B2 (en) * | 2015-09-14 | 2020-03-17 | Synvina C.V. | Process for the preparation of a polyester |
| US20200262971A1 (en) | 2015-12-22 | 2020-08-20 | Exxonmobil Chemical Patents Inc. | Terephthalate-co-4,4-bibenzoate polyesters |
| US20190276592A1 (en) | 2016-11-23 | 2019-09-12 | Exxonmobil Chemical Patents Inc. | Diacid modified copolyesters |
| WO2018097909A1 (en) | 2016-11-23 | 2018-05-31 | Exxonmobil Chemical Patents Inc. | Bibenzoate copolyesters |
| WO2019152529A1 (en) | 2018-01-31 | 2019-08-08 | Exxonmobil Chemical Patents Inc. | Fiber reinforced terephthalate-co-4,4'-bibenzoate copolyester |
| EP3768760A1 (en) | 2018-03-21 | 2021-01-27 | ExxonMobil Chemical Patents Inc. | Functionalized bifuran and synthesis thereof |
| US11001694B1 (en) | 2018-07-23 | 2021-05-11 | Kevin L. Rollick | Modification of polyester resins after melt polymerization |
| US10899881B1 (en) | 2018-07-23 | 2021-01-26 | Kevin L. Rollick | Polyester modification method |
| TW202344558A (zh) | 2022-02-16 | 2023-11-16 | 日商三菱瓦斯化學股份有限公司 | 硬化性樹脂之製造方法 |
| EP4480986A1 (en) | 2022-02-16 | 2024-12-25 | Mitsubishi Gas Chemical Company, Inc. | Curable resin, cured product of same, and resin composition |
| WO2023157777A1 (ja) | 2022-02-16 | 2023-08-24 | 三菱瓦斯化学株式会社 | 硬化性樹脂、その硬化物、樹脂組成物、及び硬化性樹脂の製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2365934C3 (de) * | 1973-08-10 | 1983-12-15 | Faserwerke Hüls GmbH, 4370 Marl | Herstellung von hochmolekularen Polyestern |
| DE2559290B2 (de) * | 1975-12-31 | 1979-08-02 | Davy International Ag, 6000 Frankfurt | Verfahren zur kontinuierlichen Herstellung von hochmolekularem PoIyäthylenterephthalat |
| US4165420A (en) * | 1977-11-10 | 1979-08-21 | The Goodyear Tire & Rubber Company | Solid state polymerization of polyester prepolymer |
| US4154920A (en) * | 1978-03-13 | 1979-05-15 | Owens-Illinois, Inc. | Methods for producing improved stable polyethylene terephthalate |
| US4161578A (en) * | 1978-05-12 | 1979-07-17 | Bepex Corporation | Process for solid phase polymerization of polyester |
-
1979
- 1979-06-12 US US90/001508A patent/US4238593B1/en not_active Expired - Lifetime
-
1980
- 1980-04-17 CA CA000350040A patent/CA1139493A/en not_active Expired
- 1980-05-09 AU AU58253/80A patent/AU532816B2/en not_active Expired
- 1980-05-20 GB GB8016605A patent/GB2051100B/en not_active Expired
- 1980-05-28 BR BR8003311A patent/BR8003311A/pt not_active IP Right Cessation
- 1980-05-28 MX MX182534A patent/MX156234A/es unknown
- 1980-06-07 KR KR1019800002246A patent/KR840000282B1/ko not_active Expired
- 1980-06-09 JP JP7760380A patent/JPS562321A/ja active Granted
- 1980-06-09 IT IT48921/80A patent/IT1128160B/it active
- 1980-06-12 BE BE0/201023A patent/BE883799A/fr not_active IP Right Cessation
- 1980-06-12 FR FR8013075A patent/FR2465759A1/fr active Granted
- 1980-06-12 DE DE19803022076 patent/DE3022076A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US4238593A (en) | 1980-12-09 |
| GB2051100A (en) | 1981-01-14 |
| JPH0212973B2 (enExample) | 1990-04-03 |
| KR840000282B1 (ko) | 1984-03-13 |
| AU532816B2 (en) | 1983-10-13 |
| GB2051100B (en) | 1983-10-26 |
| BR8003311A (pt) | 1980-12-30 |
| US4238593B1 (en) | 1994-03-22 |
| KR830002831A (ko) | 1983-05-30 |
| DE3022076A1 (de) | 1981-01-22 |
| BE883799A (fr) | 1980-10-01 |
| FR2465759B1 (enExample) | 1983-05-27 |
| JPS562321A (en) | 1981-01-12 |
| AU5825380A (en) | 1980-12-18 |
| FR2465759A1 (fr) | 1981-03-27 |
| IT1128160B (it) | 1986-05-28 |
| IT8048921A0 (it) | 1980-06-09 |
| MX156234A (es) | 1988-07-27 |
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