KR102378006B1 - 폴리이소이다이드 푸라노에이트 열가소성 폴리에스테르 및 코폴리에스테르 및 고온 충전 포장에서의 이의 용도 - Google Patents
폴리이소이다이드 푸라노에이트 열가소성 폴리에스테르 및 코폴리에스테르 및 고온 충전 포장에서의 이의 용도 Download PDFInfo
- Publication number
- KR102378006B1 KR102378006B1 KR1020217009396A KR20217009396A KR102378006B1 KR 102378006 B1 KR102378006 B1 KR 102378006B1 KR 1020217009396 A KR1020217009396 A KR 1020217009396A KR 20217009396 A KR20217009396 A KR 20217009396A KR 102378006 B1 KR102378006 B1 KR 102378006B1
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- South Korea
- Prior art keywords
- semi
- isoidide
- butanediol
- crystalline
- temperature
- 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.)
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- 229920001634 Copolyester Polymers 0.000 title claims abstract description 20
- 238000004806 packaging method and process Methods 0.000 title claims abstract description 17
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 title claims description 9
- 229920000728 polyester Polymers 0.000 title description 18
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- 239000004416 thermosoftening plastic Substances 0.000 title description 6
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 43
- KLDXJTOLSGUMSJ-UNTFVMJOSA-N (3s,3ar,6s,6ar)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-UNTFVMJOSA-N 0.000 claims abstract description 30
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 22
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 18
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229920006126 semicrystalline polymer Polymers 0.000 claims abstract description 9
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- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- NVWMHICCPUEWLL-UHFFFAOYSA-N 3,4-dimethylfuran-2,5-dicarboxylic acid Chemical compound CC=1C(C)=C(C(O)=O)OC=1C(O)=O NVWMHICCPUEWLL-UHFFFAOYSA-N 0.000 claims 1
- 238000006384 oligomerization reaction Methods 0.000 claims 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 150000002009 diols Chemical class 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 229920000139 polyethylene terephthalate Polymers 0.000 description 10
- 239000005020 polyethylene terephthalate Substances 0.000 description 10
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 9
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 9
- 229920001519 homopolymer Polymers 0.000 description 9
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- 229920001577 copolymer Polymers 0.000 description 7
- 229920001707 polybutylene terephthalate Polymers 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
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- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
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- 238000005481 NMR spectroscopy Methods 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 3
- 229940078552 o-xylene Drugs 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis 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
- AXPZIVKEZRHGAS-UHFFFAOYSA-N 3-benzyl-5-[(2-nitrophenoxy)methyl]oxolan-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1OCC1OC(=O)C(CC=2C=CC=CC=2)C1 AXPZIVKEZRHGAS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
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- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 238000001374 small-angle light scattering Methods 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 description 1
- 238000011993 High Performance Size Exclusion Chromatography Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
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- 235000015203 fruit juice Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
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- 239000005022 packaging material Substances 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- CUNPJFGIODEJLQ-UHFFFAOYSA-M potassium;2,2,2-trifluoroacetate Chemical compound [K+].[O-]C(=O)C(F)(F)F CUNPJFGIODEJLQ-UHFFFAOYSA-M 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
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- 238000013374 right angle light scattering Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000011496 sports drink Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
-
- 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
- C08G63/88—Post-polymerisation treatment
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)
- Wrappers (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461986257P | 2014-04-30 | 2014-04-30 | |
| US61/986,257 | 2014-04-30 | ||
| PCT/EP2015/059555 WO2015166070A1 (en) | 2014-04-30 | 2015-04-30 | Polyisoidide furanoate thermoplastic polyesters and copolyesters and a use thereof in hot fill packaging |
| KR1020167032214A KR20170008232A (ko) | 2014-04-30 | 2015-04-30 | 폴리이소이다이드 푸라노에이트 열가소성 폴리에스테르 및 코폴리에스테르 및 고온 충전 포장에서의 이의 용도 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020167032214A Division KR20170008232A (ko) | 2014-04-30 | 2015-04-30 | 폴리이소이다이드 푸라노에이트 열가소성 폴리에스테르 및 코폴리에스테르 및 고온 충전 포장에서의 이의 용도 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20210038997A KR20210038997A (ko) | 2021-04-08 |
| KR102378006B1 true KR102378006B1 (ko) | 2022-03-24 |
Family
ID=53039907
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020217009396A Active KR102378006B1 (ko) | 2014-04-30 | 2015-04-30 | 폴리이소이다이드 푸라노에이트 열가소성 폴리에스테르 및 코폴리에스테르 및 고온 충전 포장에서의 이의 용도 |
| KR1020167032214A Ceased KR20170008232A (ko) | 2014-04-30 | 2015-04-30 | 폴리이소이다이드 푸라노에이트 열가소성 폴리에스테르 및 코폴리에스테르 및 고온 충전 포장에서의 이의 용도 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020167032214A Ceased KR20170008232A (ko) | 2014-04-30 | 2015-04-30 | 폴리이소이다이드 푸라노에이트 열가소성 폴리에스테르 및 코폴리에스테르 및 고온 충전 포장에서의 이의 용도 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10125216B2 (enExample) |
| EP (1) | EP3137531B1 (enExample) |
| JP (1) | JP6554485B2 (enExample) |
| KR (2) | KR102378006B1 (enExample) |
| CN (1) | CN106471038B (enExample) |
| AU (1) | AU2015254523B2 (enExample) |
| BR (1) | BR112016025235B1 (enExample) |
| CA (1) | CA2946080C (enExample) |
| ES (1) | ES2758535T3 (enExample) |
| MX (1) | MX380350B (enExample) |
| WO (1) | WO2015166070A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6175501B2 (ja) * | 2012-08-31 | 2017-08-02 | ソシエテ アノニム デ ゾ ミネラル デヴィアン エ オン ナブレジェ“エス．ア．ウ．エム．ウ” | ボトルの製造方法 |
| ES2935593T3 (es) | 2015-02-24 | 2023-03-08 | Archer Daniels Midland Co | Fabricación y purificación de isoidida |
| CA3039502A1 (en) * | 2016-10-05 | 2018-04-12 | Furanix Technologies B.V. | Process for the production of a solid-state polymerized poly(tetramethylene-2,5-furan dicarboxylate) polymer and polymer thus produced |
| CN110914335A (zh) * | 2017-05-18 | 2020-03-24 | 阿凡田知识中心有限公司 | 聚酯共聚物 |
| FR3072094B1 (fr) | 2017-10-11 | 2020-09-04 | Roquette Freres | Polyester thermoplastique hautement incorpore en motif 1,4 : 3,6-dianhydro-l-iditol |
| CN108264634B (zh) * | 2018-01-29 | 2021-08-06 | 中国科学院成都有机化学有限公司 | 一种2,5-呋喃二甲酸共聚酯及其制备方法 |
| CN108467479B (zh) * | 2018-05-08 | 2021-07-06 | 成都中科普瑞净化设备有限公司 | 一种增韧2,5-呋喃二甲酸共聚酯 |
| US11447322B2 (en) * | 2019-02-21 | 2022-09-20 | Pepsico, Inc. | Beverage container |
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| US7052764B2 (en) * | 2002-12-19 | 2006-05-30 | E. I. Du Pont De Nemours And Company | Shaped articles comprising poly[(trimethylene-co-dianhydrosugar ester) dicarboxylate] or poly(trimethylene-co-dianhydro-dicarboxylate with improved stability |
| BRPI0410573B1 (pt) * | 2003-05-21 | 2015-12-01 | Dak Americas Mississippi Inc | resinas de poliéster de cristalização lenta e o método para a produção das mesmas |
| US20100160548A1 (en) * | 2006-09-15 | 2010-06-24 | Bart Adrianus Johannes Noordover | Process for the production of a dianhydrohexitol based polyester |
| IT1387503B (it) * | 2008-05-08 | 2011-04-13 | Novamont Spa | Poliestere biodegradabile alifatico-aromatico |
| IT1403611B1 (it) * | 2010-12-22 | 2013-10-31 | Novamont Spa | Composizione di poliesteri |
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| IN2014MN01416A (enExample) * | 2012-01-04 | 2015-04-03 | Pepsico Inc | |
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| FR3020811B1 (fr) * | 2014-05-09 | 2016-06-10 | Roquette Freres | Polyesters aromatiques thermoplastiques comprenant des motifs tetrahydrofuranedimethanol et acide furanedicarboxylique |
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| CA2946080C (en) | 2020-11-10 |
| BR112016025235A2 (pt) | 2017-08-15 |
| EP3137531B1 (en) | 2019-10-23 |
| CA2946080A1 (en) | 2015-11-05 |
| KR20170008232A (ko) | 2017-01-23 |
| AU2015254523B2 (en) | 2018-11-29 |
| EP3137531A1 (en) | 2017-03-08 |
| MX2016014215A (es) | 2017-06-06 |
| US10125216B2 (en) | 2018-11-13 |
| BR112016025235B1 (pt) | 2021-07-27 |
| US20170037181A1 (en) | 2017-02-09 |
| AU2015254523A1 (en) | 2016-10-27 |
| CN106471038B (zh) | 2019-12-31 |
| MX380350B (es) | 2025-03-12 |
| ES2758535T3 (es) | 2020-05-05 |
| KR20210038997A (ko) | 2021-04-08 |
| JP2017514937A (ja) | 2017-06-08 |
| CN106471038A (zh) | 2017-03-01 |
| JP6554485B2 (ja) | 2019-07-31 |
| WO2015166070A1 (en) | 2015-11-05 |
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