JP2012512279A - 脂肪族−芳香族コポリエーテルエステルの重合 - Google Patents
脂肪族−芳香族コポリエーテルエステルの重合 Download PDFInfo
- Publication number
- JP2012512279A JP2012512279A JP2011540951A JP2011540951A JP2012512279A JP 2012512279 A JP2012512279 A JP 2012512279A JP 2011540951 A JP2011540951 A JP 2011540951A JP 2011540951 A JP2011540951 A JP 2011540951A JP 2012512279 A JP2012512279 A JP 2012512279A
- Authority
- JP
- Japan
- Prior art keywords
- aliphatic
- aromatic
- acid
- sodium
- component
- 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.)
- Abandoned
Links
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 132
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 69
- 238000000034 method Methods 0.000 claims abstract description 55
- 239000000203 mixture Substances 0.000 claims abstract description 54
- 229920000642 polymer Polymers 0.000 claims abstract description 51
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 61
- -1 titanium alkoxide Chemical class 0.000 claims description 56
- 239000011734 sodium Substances 0.000 claims description 52
- 229910052708 sodium Inorganic materials 0.000 claims description 46
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 43
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- 239000000872 buffer Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 32
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 32
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 23
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- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 20
- 125000001931 aliphatic group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 14
- 238000005809 transesterification reaction Methods 0.000 claims description 14
- 235000017281 sodium acetate Nutrition 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 12
- 239000010936 titanium Substances 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 9
- 229920002472 Starch Polymers 0.000 claims description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 8
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 8
- 235000019698 starch Nutrition 0.000 claims description 8
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 claims description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 7
- 229940087562 sodium acetate trihydrate Drugs 0.000 claims description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- 239000001632 sodium acetate Substances 0.000 claims description 6
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 239000004280 Sodium formate Substances 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
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- 239000004299 sodium benzoate Substances 0.000 claims description 4
- 235000010234 sodium benzoate Nutrition 0.000 claims description 4
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 4
- 235000019254 sodium formate Nutrition 0.000 claims description 4
- CARJPEPCULYFFP-UHFFFAOYSA-N 5-Sulfo-1,3-benzenedicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 CARJPEPCULYFFP-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- DJYPJBAHKUBLSS-UHFFFAOYSA-M sodium;hydron;terephthalate Chemical compound [Na+].OC(=O)C1=CC=C(C([O-])=O)C=C1 DJYPJBAHKUBLSS-UHFFFAOYSA-M 0.000 claims description 2
- 229920005615 natural polymer Polymers 0.000 claims 1
- 238000006068 polycondensation reaction Methods 0.000 abstract description 14
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract description 12
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- 230000018044 dehydration Effects 0.000 abstract description 4
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- 229910052757 nitrogen Inorganic materials 0.000 description 26
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 17
- 238000004821 distillation Methods 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
- 238000006471 dimerization reaction Methods 0.000 description 12
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000012545 processing Methods 0.000 description 11
- 239000001913 cellulose Substances 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- 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 10
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- 238000000113 differential scanning calorimetry Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
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- 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 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003138 primary alcohols Chemical group 0.000 description 1
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- POZWVHISDXHZLV-KVVVOXFISA-M sodium;(z)-docos-13-enoate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCCCCC([O-])=O POZWVHISDXHZLV-KVVVOXFISA-M 0.000 description 1
- YKIBJOMJPMLJTB-UHFFFAOYSA-M sodium;octacosanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCCCCCCCCCCC([O-])=O YKIBJOMJPMLJTB-UHFFFAOYSA-M 0.000 description 1
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- 238000001546 stable isotope ratio mass spectrometry Methods 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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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 1
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- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
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- 239000002699 waste material Substances 0.000 description 1
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- 229920001285 xanthan gum Polymers 0.000 description 1
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- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
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- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B1/00—Layered products having a non-planar shape
-
- 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
-
- 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
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6886—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
- C08G63/78—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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
- C08L3/02—Starch; Degradation products thereof, e.g. dextrin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
- C08L67/025—Polyesters derived from dicarboxylic acids and dihydroxy compounds containing polyether sequences
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/1397—Single layer [continuous layer]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12250008P | 2008-12-15 | 2008-12-15 | |
| US61/122,500 | 2008-12-15 | ||
| PCT/US2009/067875 WO2010075030A1 (en) | 2008-12-15 | 2009-12-14 | Polymerization of aliphatic-aromatic copolyetheresters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012512279A true JP2012512279A (ja) | 2012-05-31 |
| JP2012512279A5 JP2012512279A5 (enExample) | 2013-02-07 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011540951A Abandoned JP2012512279A (ja) | 2008-12-15 | 2009-12-14 | 脂肪族−芳香族コポリエーテルエステルの重合 |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US20110229674A1 (enExample) |
| EP (2) | EP2358783A1 (enExample) |
| JP (1) | JP2012512279A (enExample) |
| KR (1) | KR20110110184A (enExample) |
| CN (1) | CN102245671A (enExample) |
| AU (1) | AU2009330405A1 (enExample) |
| WO (2) | WO2010071771A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718954B (zh) * | 2011-03-31 | 2014-10-01 | 中国石油化工股份有限公司 | 一种阻隔性聚酯及其制备方法 |
| US10200371B2 (en) | 2015-11-09 | 2019-02-05 | Silvercar, Inc. | Vehicle access systems and methods |
| WO2024094790A1 (en) | 2022-11-04 | 2024-05-10 | Clariant International Ltd | Polyesters |
| EP4612211A1 (en) | 2022-11-04 | 2025-09-10 | The Procter & Gamble Company | Fabric and home care composition |
| EP4612210A1 (en) | 2022-11-04 | 2025-09-10 | The Procter & Gamble Company | Fabric and home care composition |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3734874A (en) * | 1970-02-27 | 1973-05-22 | Eastman Kodak Co | Polyesters and polyesteramides containing ether groups and sulfonate groups in the form of a metallic salt |
| US4052368A (en) * | 1976-06-21 | 1977-10-04 | Minnesota Mining And Manufacturing Company | Water-dispellable hot melt polyester adhesives |
| US4579936A (en) * | 1984-05-11 | 1986-04-01 | Eastman Kodak Company | Ethylene terephthalate copolymers |
| JPH0216032A (ja) * | 1988-07-05 | 1990-01-19 | Diafoil Co Ltd | ポリエステル系収縮フィルム |
| US5362777A (en) | 1988-11-03 | 1994-11-08 | Ivan Tomka | Thermoplastically processable starch and a method of making it |
| US6046248A (en) * | 1994-11-15 | 2000-04-04 | Basf Aktiengesellschaft | Biodegradable polymers, the preparation thereof and the use thereof for producing biodegradable moldings |
| DE4440837A1 (de) * | 1994-11-15 | 1996-05-23 | Basf Ag | Biologisch abbaubare Polymere, Verfahren zu deren Herstellung sowie deren Verwendung zur Herstellung bioabbaubarer Formkörper |
| US5936045A (en) | 1995-02-16 | 1999-08-10 | Basf Aktiengesellschaft | Biodegradable polymers, the preparation thereof, and the use thereof for producing biodegradable moldings |
| US5686276A (en) * | 1995-05-12 | 1997-11-11 | E. I. Du Pont De Nemours And Company | Bioconversion of a fermentable carbon source to 1,3-propanediol by a single microorganism |
| US5633362A (en) * | 1995-05-12 | 1997-05-27 | E. I. Du Pont De Nemours And Company | Production of 1,3-propanediol from glycerol by recombinant bacteria expressing recombinant diol dehydratase |
| US7919658B2 (en) * | 2003-05-06 | 2011-04-05 | E. I. Du Pont De Nemours And Company | Purification of biologically-produced 1,3-propanediol |
| US7084311B2 (en) * | 2003-05-06 | 2006-08-01 | E. I. Du Pont De Nemours And Company | Hydrogenation of chemically derived 1,3-propanediol |
| BRPI0410686A (pt) | 2003-05-06 | 2006-06-20 | Du Pont | processo e composição |
| US7144632B2 (en) | 2003-06-11 | 2006-12-05 | E. I. Du Pont De Nemours And Company | Aliphatic-aromatic polyetherester compositions, articles, films, coating and laminates and processes for producing same |
| US7220815B2 (en) * | 2003-07-31 | 2007-05-22 | E.I. Du Pont De Nemours And Company | Sulfonated aliphatic-aromatic copolyesters and shaped articles produced therefrom |
| US7452927B2 (en) * | 2004-01-30 | 2008-11-18 | E. I. Du Pont De Nemours And Company | Aliphatic-aromatic polyesters, and articles made therefrom |
| WO2006009232A1 (ja) * | 2004-07-20 | 2006-01-26 | Solotex Corporation | ポリトリメチレンテレフタレート |
| ITMI20050452A1 (it) * | 2005-03-18 | 2006-09-19 | Novamont Spa | Poliestere biodegradabile alifatico-aromatico |
| US7696299B2 (en) * | 2006-02-21 | 2010-04-13 | Futura Polyesters Limited | Fast crystallizing modified polyethylene naphthalate |
-
2009
- 2009-12-14 AU AU2009330405A patent/AU2009330405A1/en not_active Abandoned
- 2009-12-14 JP JP2011540951A patent/JP2012512279A/ja not_active Abandoned
- 2009-12-14 EP EP09774793A patent/EP2358783A1/en not_active Withdrawn
- 2009-12-14 WO PCT/US2009/067863 patent/WO2010071771A1/en not_active Ceased
- 2009-12-14 US US13/128,920 patent/US20110229674A1/en not_active Abandoned
- 2009-12-14 EP EP09768595A patent/EP2365992A1/en not_active Withdrawn
- 2009-12-14 US US13/127,067 patent/US20110206883A1/en not_active Abandoned
- 2009-12-14 CN CN2009801505034A patent/CN102245671A/zh active Pending
- 2009-12-14 KR KR1020117016358A patent/KR20110110184A/ko not_active Withdrawn
- 2009-12-14 WO PCT/US2009/067875 patent/WO2010075030A1/en not_active Ceased
-
2012
- 2012-12-28 US US13/729,787 patent/US20130129951A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010071771A1 (en) | 2010-06-24 |
| EP2365992A1 (en) | 2011-09-21 |
| AU2009330405A1 (en) | 2010-07-01 |
| US20110206883A1 (en) | 2011-08-25 |
| US20110229674A1 (en) | 2011-09-22 |
| WO2010075030A1 (en) | 2010-07-01 |
| CN102245671A (zh) | 2011-11-16 |
| KR20110110184A (ko) | 2011-10-06 |
| AU2009330405A2 (en) | 2011-05-19 |
| US20130129951A1 (en) | 2013-05-23 |
| EP2358783A1 (en) | 2011-08-24 |
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