JP6576011B2 - ポリブチレンテレフタレートオリゴマーを製造する方法 - Google Patents
ポリブチレンテレフタレートオリゴマーを製造する方法 Download PDFInfo
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- JP6576011B2 JP6576011B2 JP2017508001A JP2017508001A JP6576011B2 JP 6576011 B2 JP6576011 B2 JP 6576011B2 JP 2017508001 A JP2017508001 A JP 2017508001A JP 2017508001 A JP2017508001 A JP 2017508001A JP 6576011 B2 JP6576011 B2 JP 6576011B2
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- 229920001707 polybutylene terephthalate Polymers 0.000 title claims description 246
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- -1 polybutylene terephthalate Polymers 0.000 title claims description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 142
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 131
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical group CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 89
- 238000000034 method Methods 0.000 claims description 67
- 230000008569 process Effects 0.000 claims description 46
- 239000003054 catalyst Substances 0.000 claims description 39
- 238000002844 melting Methods 0.000 claims description 39
- 230000008018 melting Effects 0.000 claims description 39
- 229920000642 polymer Polymers 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 14
- 238000011179 visual inspection Methods 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims 2
- 238000005453 pelletization Methods 0.000 claims 1
- 238000010298 pulverizing process Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 71
- 238000005809 transesterification reaction Methods 0.000 description 59
- 239000000523 sample Substances 0.000 description 45
- 239000000155 melt Substances 0.000 description 43
- 239000012299 nitrogen atmosphere Substances 0.000 description 28
- 238000012546 transfer Methods 0.000 description 27
- 229920005989 resin Polymers 0.000 description 23
- 239000011347 resin Substances 0.000 description 23
- 238000004458 analytical method Methods 0.000 description 22
- 150000002148 esters Chemical group 0.000 description 20
- 238000006467 substitution reaction Methods 0.000 description 20
- 238000005886 esterification reaction Methods 0.000 description 18
- 230000000694 effects Effects 0.000 description 15
- 230000032050 esterification Effects 0.000 description 14
- 238000006068 polycondensation reaction Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 230000007423 decrease Effects 0.000 description 12
- 238000010924 continuous production Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000005259 measurement Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000011049 filling Methods 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 6
- 230000000007 visual effect Effects 0.000 description 6
- 230000003247 decreasing effect Effects 0.000 description 5
- 238000010309 melting process Methods 0.000 description 5
- 238000005457 optimization Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000012812 general test Methods 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 230000001936 parietal effect Effects 0.000 description 2
- 238000011020 pilot scale process Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920006309 Invista Polymers 0.000 description 1
- 235000017284 Pometia pinnata Nutrition 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000007704 transition Effects 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
- C08G63/02—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
-
- 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
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462037859P | 2014-08-15 | 2014-08-15 | |
| US62/037,859 | 2014-08-15 | ||
| PCT/US2015/045010 WO2016025687A1 (en) | 2014-08-15 | 2015-08-13 | Process for making polybutylene terephthalate oligomers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017529424A JP2017529424A (ja) | 2017-10-05 |
| JP2017529424A5 JP2017529424A5 (enExample) | 2018-07-19 |
| JP6576011B2 true JP6576011B2 (ja) | 2019-09-18 |
Family
ID=53887250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017508001A Active JP6576011B2 (ja) | 2014-08-15 | 2015-08-13 | ポリブチレンテレフタレートオリゴマーを製造する方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US10233282B2 (enExample) |
| EP (1) | EP3194467A1 (enExample) |
| JP (1) | JP6576011B2 (enExample) |
| CN (1) | CN107001600B (enExample) |
| WO (1) | WO2016025687A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11180607B2 (en) * | 2019-12-10 | 2021-11-23 | Chang Chun Plastics Co., Ltd. | Polyesters with ultra-high flowability and superior stability and meltblown fibers thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4346213A (en) * | 1980-08-25 | 1982-08-24 | Celanese Corporation | Process for the preparation of polybutylene terephthalate |
| US6472500B2 (en) * | 2000-06-17 | 2002-10-29 | General Electric Company | Crystalline polyester resins and processes for their preparation |
| JP2004035742A (ja) * | 2002-07-04 | 2004-02-05 | General Electric Co <Ge> | 結晶性ポリエステル樹脂及びその製法 |
| CN1472234A (zh) * | 2002-07-31 | 2004-02-04 | 通用电气公司 | 结晶聚酯树脂及其制备方法 |
| JP2005105262A (ja) * | 2003-09-09 | 2005-04-21 | Mitsubishi Chemicals Corp | ポリブチレンテレフタレート及びその製造方法 |
| JP5079226B2 (ja) * | 2005-08-29 | 2012-11-21 | 三菱化学株式会社 | ポリブチレンテレフタレート |
-
2015
- 2015-08-13 US US15/322,570 patent/US10233282B2/en active Active
- 2015-08-13 EP EP15753296.1A patent/EP3194467A1/en not_active Withdrawn
- 2015-08-13 JP JP2017508001A patent/JP6576011B2/ja active Active
- 2015-08-13 WO PCT/US2015/045010 patent/WO2016025687A1/en not_active Ceased
- 2015-08-13 CN CN201580051279.9A patent/CN107001600B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2017529424A (ja) | 2017-10-05 |
| CN107001600B (zh) | 2019-11-19 |
| WO2016025687A1 (en) | 2016-02-18 |
| US10233282B2 (en) | 2019-03-19 |
| CN107001600A (zh) | 2017-08-01 |
| US20180201729A1 (en) | 2018-07-19 |
| EP3194467A1 (en) | 2017-07-26 |
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