JP2014524958A - ポリ(ブチレン−コ−アジパートテレフタレート)の色安定化法 - Google Patents
ポリ(ブチレン−コ−アジパートテレフタレート)の色安定化法 Download PDFInfo
- Publication number
- JP2014524958A JP2014524958A JP2014520355A JP2014520355A JP2014524958A JP 2014524958 A JP2014524958 A JP 2014524958A JP 2014520355 A JP2014520355 A JP 2014520355A JP 2014520355 A JP2014520355 A JP 2014520355A JP 2014524958 A JP2014524958 A JP 2014524958A
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- JP
- Japan
- Prior art keywords
- poly
- group
- copolyester
- combinations
- terephthalate
- 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.)
- Pending
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- 238000000034 method Methods 0.000 title claims abstract description 34
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 title description 3
- 230000006641 stabilisation Effects 0.000 title 1
- 238000011105 stabilization Methods 0.000 title 1
- 229920001634 Copolyester Polymers 0.000 claims abstract description 122
- 125000003118 aryl group Chemical group 0.000 claims abstract description 91
- 239000000203 mixture Substances 0.000 claims abstract description 90
- 229920000728 polyester Polymers 0.000 claims abstract description 85
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 87
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 80
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 77
- 150000001875 compounds Chemical class 0.000 claims description 75
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical group OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 67
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid group Chemical group C(CCCCC(=O)O)(=O)O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 45
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 38
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical group OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 35
- 229920002215 polytrimethylene terephthalate Polymers 0.000 claims description 32
- 125000003158 alcohol group Chemical group 0.000 claims description 31
- 125000001931 aliphatic group Chemical group 0.000 claims description 29
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 28
- 239000000654 additive Substances 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 26
- -1 alkaline earth metal salt Chemical class 0.000 claims description 25
- 229920001577 copolymer Polymers 0.000 claims description 25
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 24
- 150000002009 diols Chemical class 0.000 claims description 23
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical group OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 23
- 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 claims description 22
- 239000001361 adipic acid Substances 0.000 claims description 22
- 235000011037 adipic acid Nutrition 0.000 claims description 22
- 239000003208 petroleum Substances 0.000 claims description 21
- 239000004593 Epoxy Substances 0.000 claims description 20
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 20
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical group C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 19
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 18
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 17
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 17
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical group OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 16
- 239000010936 titanium Substances 0.000 claims description 16
- 229910052719 titanium Inorganic materials 0.000 claims description 16
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 15
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical group OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 claims description 15
- 230000000996 additive effect Effects 0.000 claims description 14
- 235000010355 mannitol Nutrition 0.000 claims description 14
- 229960001047 methyl salicylate Drugs 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 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 claims description 11
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 11
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims description 10
- 229920005862 polyol Polymers 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 10
- 229960002920 sorbitol Drugs 0.000 claims description 10
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical group O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 9
- 229920003232 aliphatic polyester Polymers 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 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 claims description 8
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical group CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003700 epoxy group Chemical group 0.000 claims description 8
- 229920000515 polycarbonate Polymers 0.000 claims description 8
- 239000004417 polycarbonate Substances 0.000 claims description 8
- 229920000647 polyepoxide Polymers 0.000 claims description 8
- BNNBECJSDDMHFF-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclobutane-1,1-diol Chemical compound CC1(C)CC(O)(O)C1(C)C BNNBECJSDDMHFF-UHFFFAOYSA-N 0.000 claims description 7
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical group CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 7
- 229910017052 cobalt Inorganic materials 0.000 claims description 7
- 239000010941 cobalt Substances 0.000 claims description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
- 229930195725 Mannitol Natural products 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 229920002472 Starch Polymers 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001447 alkali salts Chemical class 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052787 antimony Inorganic materials 0.000 claims description 6
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 235000006708 antioxidants Nutrition 0.000 claims description 6
- 238000003490 calendering Methods 0.000 claims description 6
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 6
- 229910052732 germanium Inorganic materials 0.000 claims description 6
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 6
- 229940051250 hexylene glycol Drugs 0.000 claims description 6
- 229960002479 isosorbide Drugs 0.000 claims description 6
- 239000000594 mannitol Substances 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 6
- 239000004626 polylactic acid Substances 0.000 claims description 6
- 239000000600 sorbitol Substances 0.000 claims description 6
- 235000010356 sorbitol Nutrition 0.000 claims description 6
- 235000019698 starch Nutrition 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000005286 illumination Methods 0.000 claims description 5
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical group C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 claims description 5
- 239000004014 plasticizer Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- ZMKVBUOZONDYBW-UHFFFAOYSA-N 1,6-dioxecane-2,5-dione Chemical compound O=C1CCC(=O)OCCCCO1 ZMKVBUOZONDYBW-UHFFFAOYSA-N 0.000 claims description 4
- 239000012963 UV stabilizer Substances 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 230000003712 anti-aging effect Effects 0.000 claims description 4
- 239000001273 butane Substances 0.000 claims description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 4
- 238000001125 extrusion Methods 0.000 claims description 4
- 239000002667 nucleating agent Substances 0.000 claims description 4
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 claims description 4
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims description 4
- 239000008107 starch Substances 0.000 claims description 4
- 238000005292 vacuum distillation Methods 0.000 claims description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 3
- AXKZIDYFAMKWSA-UHFFFAOYSA-N 1,6-dioxacyclododecane-7,12-dione Chemical compound O=C1CCCCC(=O)OCCCCO1 AXKZIDYFAMKWSA-UHFFFAOYSA-N 0.000 claims description 3
- 239000004970 Chain extender Substances 0.000 claims description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 3
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- 235000011090 malic acid Nutrition 0.000 claims description 3
- 229940099690 malic acid Drugs 0.000 claims description 3
- 229960001855 mannitol Drugs 0.000 claims description 3
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 3
- 229940059574 pentaerithrityl Drugs 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- 229920001610 polycaprolactone Polymers 0.000 claims description 3
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- 239000000811 xylitol Substances 0.000 claims description 3
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 3
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- 238000000071 blow moulding Methods 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical group OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- YNJCGEDVIOLRLB-UHFFFAOYSA-N 1,1,2,2-tetramethylcyclobutane Chemical compound CC1(C)CCC1(C)C YNJCGEDVIOLRLB-UHFFFAOYSA-N 0.000 claims 1
- CKXDKAOBYWWYEK-UHFFFAOYSA-N 1,6-dioxecane-2,5-dione;hexanedioic acid Chemical compound OC(=O)CCCCC(O)=O.O=C1CCC(=O)OCCCCO1 CKXDKAOBYWWYEK-UHFFFAOYSA-N 0.000 claims 1
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 10
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- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 7
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 7
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- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
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- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
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- 230000014509 gene expression Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
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- 230000007062 hydrolysis Effects 0.000 description 1
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- 238000002347 injection Methods 0.000 description 1
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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 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
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- 239000006082 mold release agent Substances 0.000 description 1
- 239000010813 municipal solid waste Substances 0.000 description 1
- 125000005486 naphthalic acid group Chemical group 0.000 description 1
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- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
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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
- C08G63/02—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
- C08G63/02—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
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
- C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
- C08J11/24—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/05—Alcohols; Metal alcoholates
- C08K5/053—Polyhydroxylic alcohols
-
- 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Biological Depolymerization Polymers (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/183,807 US8877862B2 (en) | 2011-07-15 | 2011-07-15 | Method for color stabilization of poly(butylene-co-adipate terephthalate |
| US13/183,807 | 2011-07-15 | ||
| PCT/US2012/046625 WO2013012705A1 (en) | 2011-07-15 | 2012-07-13 | Method for color stabilization of poly(butylene-co-adipate terephthalate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014524958A true JP2014524958A (ja) | 2014-09-25 |
| JP2014524958A5 JP2014524958A5 (enExample) | 2015-04-09 |
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| JP2014520355A Pending JP2014524958A (ja) | 2011-07-15 | 2012-07-13 | ポリ(ブチレン−コ−アジパートテレフタレート)の色安定化法 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US8877862B2 (enExample) |
| EP (1) | EP2731980B1 (enExample) |
| JP (1) | JP2014524958A (enExample) |
| CN (1) | CN103703049B (enExample) |
| AU (1) | AU2012284304B2 (enExample) |
| WO (1) | WO2013012705A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020535286A (ja) * | 2017-09-28 | 2020-12-03 | フラウンホーファー−ゲゼルシャフト ツゥア フェアデルング デア アンゲヴァンドテン フォァシュング エー.ファウ. | ハロゲンフリー熱可塑性リサイクル材を安定化するための方法、安定化プラスチック組成物、ならびにそれから生成される成形コンパウンドおよび成形部品 |
| JP2023535882A (ja) * | 2020-07-06 | 2023-08-22 | アクアパック ポリマーズ リミテッド | ポリビニルアルコールの製造方法及びその製造装置 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9334360B2 (en) | 2011-07-15 | 2016-05-10 | Sabic Global Technologies B.V. | Color-stabilized biodegradable aliphatic-aromatic copolyesters, methods of manufacture, and articles thereof |
| US8946345B2 (en) | 2011-08-30 | 2015-02-03 | Saudi Basic Industries Corporation | Method for the preparation of (polybutylene-co-adipate terephthalate) through the in situ phosphorus containing titanium based catalyst |
| US9034983B2 (en) | 2012-03-01 | 2015-05-19 | Saudi Basic Industries Corporation | Poly(butylene-co-adipate terephthalate), method of manufacture and uses thereof |
| US9670313B2 (en) | 2012-07-30 | 2017-06-06 | Sabic Global Technologies B.V. | Hydrostability of polyester composition |
| WO2014022197A1 (en) | 2012-07-30 | 2014-02-06 | Sabic Innovative Plastics Ip B.V. | Method for preparation of modified poly(alkylene terephthalate) employing titanium-containing catalyst complex |
| US9487622B2 (en) | 2013-07-25 | 2016-11-08 | Sabic Global Technologies B.V. | Process for the preparation of modified poly(alkylene terephthalate) employing an in-situ titanium-containing catalyst |
| KR101571750B1 (ko) * | 2014-01-28 | 2015-11-25 | 한국기술교육대학교 산학협력단 | 아이소소르바이드가 함유된 폴리에스터를 포함하는 고분자 복합체 및 그 제조방법 |
| WO2016053158A1 (en) * | 2014-10-02 | 2016-04-07 | Perstorp Ab | A thermoplastic composition with improved flow rate |
| US9738752B2 (en) * | 2015-04-24 | 2017-08-22 | Xerox Corporation | Copolymers for 3D printing |
| CN107974051A (zh) * | 2016-10-21 | 2018-05-01 | 中国石油化工股份有限公司 | 一种聚酯组合物及其制备方法 |
| CN107974050A (zh) * | 2016-10-21 | 2018-05-01 | 中国石油化工股份有限公司 | 一种聚酯组合物及其制备方法 |
| ES2876266T5 (en) | 2017-05-31 | 2025-03-05 | Basf Se | Aliphatic-aromatic polyesters having an increased white level index |
| KR102664171B1 (ko) | 2017-07-07 | 2024-05-17 | 스테판 컴파니 | 폴리우레탄 적용을 위한 저점도 폴리올 |
| CN108456297A (zh) * | 2018-01-23 | 2018-08-28 | 浙江省现代纺织工业研究院 | 一种差别化eg的制备方法 |
| CN109503819B (zh) * | 2019-01-04 | 2021-09-21 | 中国科学院成都有机化学有限公司 | 一种合成pbt聚酯的方法 |
| WO2021072020A1 (en) * | 2019-10-08 | 2021-04-15 | Eastman Chemical Company | Catalyst systems for crystallizable reactor grade resins with recycled content |
| EP4048727A1 (en) * | 2019-10-25 | 2022-08-31 | Eastman Chemical Company | Crystallizable shrinkable films and thermoformable films and sheets made from reactor grade resins with recycled content |
| US20230091692A1 (en) * | 2021-09-20 | 2023-03-23 | Carl David Bodam | Pressurized tube sealing for containers |
| WO2025128797A1 (en) | 2023-12-13 | 2025-06-19 | Blue Evolution, Inc | Ecofriendly, biodegradable biological polysaccharide composition for packaging materials |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007314743A (ja) * | 2006-04-27 | 2007-12-06 | Seiko Pmc Corp | ポリエステル系樹脂の製造方法、及びその製造方法により得られたポリエステル系樹脂、並びに該樹脂を用いたトナー用樹脂 |
| JP2011093986A (ja) * | 2009-10-28 | 2011-05-12 | Nippon Ester Co Ltd | ポリエステルの製造方法及びポリエステル |
| JP2014520933A (ja) * | 2011-07-15 | 2014-08-25 | サウディ ベーシック インダストリーズ コーポレイション | 色が安定な生分解性脂肪族/芳香族共重合ポリエステル、製造方法、及びその物品 |
Family Cites Families (139)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2012267A (en) | 1929-08-01 | 1935-08-27 | Du Pont | Alkylene ester of polybasic acids |
| US2830966A (en) | 1955-02-11 | 1958-04-15 | American Cyanamid Co | Unsaturated polyester resin composition containing indan carboxylic acids and process of preparing the same |
| US2780609A (en) | 1955-02-23 | 1957-02-05 | American Cyanamid Co | Plasticized vinyl chloride polymer |
| US2873262A (en) | 1955-10-10 | 1959-02-10 | American Cyanamid Co | Novel alkyd resins prepared from indandicarboxylic acids and the process of preparing the same |
| US3102135A (en) | 1961-10-10 | 1963-08-27 | American Cyanamid Co | Production of benzoic acids and 1-(carboxyphenyl)-indane carboxylic acids |
| US3547888A (en) | 1967-06-05 | 1970-12-15 | Mobil Oil Corp | Amorphous terpolyesters having high impact strength |
| US3522215A (en) | 1967-06-05 | 1970-07-28 | Mobil Oil Corp | Impact resistant amorphous copolyesters |
| US3535286A (en) | 1968-04-10 | 1970-10-20 | Goodyear Tire & Rubber | Terephthalic acid-phenyl indane dicarboxylic acid copolyester resin |
| US3634089A (en) | 1969-04-04 | 1972-01-11 | Eastman Kodak Co | Film-forming polyester compositions |
| US3669921A (en) | 1971-02-08 | 1972-06-13 | Eastman Kodak Co | Copolyester melt adhesive |
| US3769264A (en) | 1971-11-01 | 1973-10-30 | Eastman Kodak Co | Film forming condensation polymers |
| US3833685A (en) | 1972-03-10 | 1974-09-03 | Gen Electric | Flame retardant thermoplastic compositions |
| US3989664A (en) | 1972-11-24 | 1976-11-02 | Teijin Limited | Stabilized polyester composition and method for stabilizing polyester |
| JPS5323876B2 (enExample) | 1973-03-22 | 1978-07-17 | ||
| US3953539A (en) | 1973-03-28 | 1976-04-27 | Teijin Ltd. | Aromatic polyester resin composition having inhibited coloration and method for inhibiting coloration |
| US3856752A (en) | 1973-10-01 | 1974-12-24 | Ciba Geigy Corp | Soluble polyimides derived from phenylindane diamines and dianhydrides |
| DE2431072C3 (de) | 1974-06-28 | 1980-04-30 | Bayer Ag, 5090 Leverkusen | Thermoplastische Copolyester und Verfahren zu ihrer Herstellung |
| US4128526A (en) | 1976-12-23 | 1978-12-05 | General Electric Company | Copolyesters of poly(alkylene glycol aromatic acid esters) and diesters comprising aromatic diols |
| DE2727486C2 (de) | 1977-06-18 | 1982-09-16 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von thermoplastischen Formmassen |
| US4202785A (en) | 1978-05-15 | 1980-05-13 | Eastman Kodak Company | Polyesterionomers having utility in liquid electrographic developer compositions |
| DE2945729C2 (de) | 1979-11-13 | 1982-06-09 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von hochmolekularen, linearen Polyestern |
| US4401804A (en) | 1982-05-24 | 1983-08-30 | Eastman Kodak Company | Deactivation of polyester catalyst residues |
| US4418188A (en) | 1982-09-07 | 1983-11-29 | The Goodyear Tire & Rubber Company | Polyethylene isophthalate having reduced cyclic dimer content and process therefore |
| JPS5978234A (ja) | 1982-10-28 | 1984-05-07 | Toyo Seikan Kaisha Ltd | ホツトメルト接着剤 |
| DE3300315A1 (de) | 1983-01-07 | 1984-07-12 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur herstellung von hellfarbigen polyestern unter verwendung von titankatalysatoren |
| US4452933A (en) | 1983-06-09 | 1984-06-05 | General Electric Company | Stabilized polyester-polycarbonate blends and stabilization process therefor |
| JPS60240724A (ja) | 1984-05-14 | 1985-11-29 | Kuraray Co Ltd | 共重合ポリエステルフイルム並びに該フイルムからなるホツトメルト接着剤 |
| US4617373A (en) | 1985-02-15 | 1986-10-14 | Eastman Kodak Company | Condensation polymers and products therefrom |
| EP0272417A3 (en) | 1986-12-22 | 1989-09-27 | General Electric Company | Blends of polycarbonate resins and polyester resins exhibiting improved color properties |
| US5271985A (en) | 1987-08-28 | 1993-12-21 | Toray Industries, Inc. | Polyester film having specific surface properties |
| DE3850382T2 (de) | 1987-08-28 | 1995-01-19 | Toray Industries | Polyester-film. |
| GB9012524D0 (en) | 1990-06-05 | 1990-07-25 | Shell Int Research | High surface area zirconia,a process for producing high surface area zirconia and a process for the production of hydrocarbons from synthesis gas |
| US5292783A (en) | 1990-11-30 | 1994-03-08 | Eastman Kodak Company | Aliphatic-aromatic copolyesters and cellulose ester/polymer blends |
| US6495656B1 (en) | 1990-11-30 | 2002-12-17 | Eastman Chemical Company | Copolyesters and fibrous materials formed therefrom |
| DE69132548T2 (de) | 1990-11-30 | 2001-06-28 | Eastman Chemical Co., Kingsport | Aliphatisch-aromatische Copolyester |
| IT1245408B (it) | 1991-02-20 | 1994-09-20 | Butterfly Srl | Composizioni polimeriche biodegradabili a base di amido e di polimero termoplastico |
| JPH05140277A (ja) | 1991-11-18 | 1993-06-08 | Teijin Ltd | 水性ポリエステル、これを塗設した易接着性ポリエステルフイルム及びその製造方法 |
| EP0573680A1 (en) | 1992-06-05 | 1993-12-15 | General Electric Company | Impact modified polyester and/or polycarbonate |
| DE4220473A1 (de) | 1992-06-23 | 1994-01-05 | Zimmer Ag | Verfahren zur Herstellung von Polybutylenterephthalat aus PET-Abfall |
| US5844023A (en) | 1992-11-06 | 1998-12-01 | Bio-Tec Biologische Naturverpackungen Gmbh | Biologically degradable polymer mixture |
| US5453479A (en) | 1993-07-12 | 1995-09-26 | General Electric Company | Polyesterification catalyst |
| US5498749A (en) | 1993-10-22 | 1996-03-12 | Eastman Chemical Company | Process for separating cyclohexane dimethanol from dimethyl terephthalate |
| US5413681A (en) | 1993-11-15 | 1995-05-09 | Eastman Chemical Company | Process for the recovery of terephthalic acid and ethylene glycol from poly(ethylene terephthalate) |
| US5391263A (en) | 1994-01-26 | 1995-02-21 | E. I. Du Pont De Nemours And Company | Process for the separation of glycols from dimethyl terephthalate |
| US5378796A (en) | 1994-02-09 | 1995-01-03 | Eastman Chemical Company | Process for preparing copolyesters |
| US5466777A (en) | 1994-03-28 | 1995-11-14 | General Electric Company | Xanthene polymers, and copolymers, and method for making |
| US5451611A (en) | 1994-03-29 | 1995-09-19 | Council Of Scientific & Industrial Research | Process for the conversion of poly(ethylene terephthalate) waste to poly(alkylene terephthalate) |
| DE4440850A1 (de) | 1994-11-15 | 1996-05-23 | Basf Ag | Biologisch abbaubare Polymere, Verfahren zu deren Herstellung sowie deren Verwendung zur Herstellung bioabbaubarer Formkörper |
| DE4440858A1 (de) | 1994-11-15 | 1996-05-23 | Basf Ag | Biologisch abbaubare Polymere, Verfahren zu deren Herstellung sowie deren Verwendung zur Herstellung bioabbaubarer Formkörper |
| US6096809A (en) | 1995-04-07 | 2000-08-01 | Bio-Tec Biologische Naturverpackungen Gmbh & Co. Kg | Biologically degradable polymer mixture |
| US5554657A (en) | 1995-05-08 | 1996-09-10 | Shell Oil Company | Process for recycling mixed polymer containing polyethylene terephthalate |
| US6384129B1 (en) | 1995-08-30 | 2002-05-07 | General Electric Company | Semi-batch emulsion process for making diene rubber latex, rubber latex made thereby, and graft copolymer made therefrom |
| US5559159A (en) | 1995-12-07 | 1996-09-24 | Eastman Chemical Company | Process including depolymerization in polyester reactor for recycling polyester materials |
| US5744503A (en) | 1996-02-01 | 1998-04-28 | Hoechst Celanese Corporation | Recycling polyester and recovering glycols |
| US5661193A (en) | 1996-05-10 | 1997-08-26 | Eastman Chemical Company | Biodegradable foamable co-polyester compositions |
| GB9612161D0 (en) | 1996-06-11 | 1996-08-14 | Tioxide Specialties Ltd | Esterification process |
| DE19624641A1 (de) | 1996-06-20 | 1998-01-08 | Biotec Biolog Naturverpack | Biologisch abbaubarer Werkstoff, bestehend im wesentlichen aus oder auf Basis thermoplastischer Stärke |
| DE19638488A1 (de) | 1996-09-20 | 1998-03-26 | Basf Ag | Biologisch abbaubare Polyester |
| DE19643479B4 (de) | 1996-10-22 | 2006-04-20 | Zimmer Ag | Verfahren zur Herstellung von Polyethylenterephthalat aus Polyethylenterephthalat-Abfall |
| DK0947559T3 (da) | 1996-11-05 | 2005-02-14 | Novamont Spa | Biologisk nedbrydelige polymersammensætninger, som indeholder stivelse og en termoplastisk polymer |
| AUPP261498A0 (en) | 1998-03-27 | 1998-04-23 | Swig Pty Ltd | Improved conversion of contaminated polyethylene terephthalate to polybutylene terephthalate |
| US6066714A (en) | 1998-04-17 | 2000-05-23 | E. I. Du Pont De Nemours And Company | Titanium-containing catalyst composition and processes therefor and therewith |
| US6133404A (en) | 1998-12-26 | 2000-10-17 | National Institute Of Technology And Quality | Polyester and formation process thereof |
| US6472557B1 (en) | 1999-02-10 | 2002-10-29 | Eastman Chemical Company | Process for recycling polyesters |
| US7037959B1 (en) | 1999-04-12 | 2006-05-02 | The United States Of America As Represented By The Secretary Of The Agriculture | Biodegradable polymer compositions methods for making same and articles therefrom |
| US20020111409A1 (en) | 1999-05-28 | 2002-08-15 | Talibuddin Sapna H. | Polyester compositions having improved color stability |
| EP1200505B1 (en) | 1999-08-06 | 2004-07-07 | Eastman Chemical Company | Polyesters having a controlled melting point and fibers formed therefrom |
| DE60029289T2 (de) | 1999-10-05 | 2007-07-26 | Nippon Shokubai Co., Ltd. | Biologisch abbaubare Polyesterharzzusammensetzung und ihre Verwendung |
| US6383729B1 (en) | 1999-10-21 | 2002-05-07 | Konica Corporation | Photographic support and photothermographic material by use thereof |
| CN1203037C (zh) | 1999-10-22 | 2005-05-25 | 帝人株式会社 | 从聚酯废料中分离和回收对苯二甲酸二甲酯和乙二醇的方法 |
| US6166170A (en) | 1999-12-02 | 2000-12-26 | E. I. Du Pont De Nemours And Company | Esterification catalysts and processes therefor and therewith |
| KR100366484B1 (ko) | 1999-12-11 | 2003-01-14 | 주식회사 이래화학 | 코폴리에스테르 수지 조성물 및 그 제조방법 |
| US6231970B1 (en) | 2000-01-11 | 2001-05-15 | E. Khashoggi Industries, Llc | Thermoplastic starch compositions incorporating a particulate filler component |
| IT1320163B1 (it) | 2000-02-15 | 2003-11-18 | Novamont Spa | Foglia e prodotti formati a base di amido espanso. |
| US6303738B1 (en) | 2000-08-04 | 2001-10-16 | E. I. Du Pont De Nemours And Company | Esterification process |
| JP5288676B2 (ja) | 2000-08-22 | 2013-09-11 | 三井化学株式会社 | ポリエステル製造用触媒、ポリエステルの製造方法およびポリエステル |
| US6573340B1 (en) | 2000-08-23 | 2003-06-03 | Biotec Biologische Naturverpackungen Gmbh & Co. Kg | Biodegradable polymer films and sheets suitable for use as laminate coatings as well as wraps and other packaging materials |
| JP3443409B2 (ja) | 2000-09-06 | 2003-09-02 | 関西ペイント株式会社 | ポリエステル樹脂の製造方法 |
| WO2002042253A1 (en) | 2000-11-27 | 2002-05-30 | Teijin Limited | Dimethyl terephthalate composition and process for producing the same |
| ITTO20010059A1 (it) | 2001-01-25 | 2002-07-25 | Novamont Spa | Miscele ternarie di poliesteri alifatici biodegradabili e prodotti daqueste ottenuti. |
| ITTO20010057A1 (it) | 2001-01-25 | 2002-07-25 | Novamont Spa | Miscele ternarie di poliesteri biodegradabili e prodotti da queste ottenuti. |
| ITTO20010060A1 (it) | 2001-01-25 | 2002-07-25 | Novamont Spa | Miscele ternartie di poliesteri alifatici biodegradabili e prodotti da queste ottenuti. |
| US7241832B2 (en) | 2002-03-01 | 2007-07-10 | bio-tec Biologische Naturverpackungen GmbH & Co., KG | Biodegradable polymer blends for use in making films, sheets and other articles of manufacture |
| US6660211B2 (en) | 2001-04-23 | 2003-12-09 | Kimberly-Clark Worldwide, Inc. | Methods of making biodegradable films having enhanced ductility and breathability |
| US6703115B2 (en) | 2001-05-01 | 2004-03-09 | Eastman Chemical Company | Multilayer films |
| BR0211556A (pt) | 2001-08-01 | 2004-07-13 | Fuller H B Licensing Financ | Composição respirável biodegradável fundida por calor |
| US20040081839A1 (en) | 2001-09-05 | 2004-04-29 | Koji Kubo | Polyester film being easy to adhere to ink receiving layer |
| WO2003033581A1 (en) | 2001-10-16 | 2003-04-24 | Teijin Limited | Method for recycling pet bottle |
| WO2003051956A1 (en) | 2001-12-15 | 2003-06-26 | Samsung Electronics Co., Ltd. | Recycled method for a wasted polyester and reclaimed materials thereof |
| CN1628151A (zh) | 2002-02-05 | 2005-06-15 | 三井化学株式会社 | 生物降解性树脂组合物及其成型体 |
| US20060257676A1 (en) | 2003-05-27 | 2006-11-16 | Mitsuyoshi Itada | Biodegradable resin film or sheet and process for producing the same |
| US6998462B2 (en) | 2003-06-11 | 2006-02-14 | E.I. Du Pont De Nemours And Company | Polyester process |
| GB0323386D0 (en) | 2003-10-07 | 2003-11-05 | Johnson Matthey Plc | Catalyst for manufacture of esters |
| BRPI0415107B1 (pt) | 2003-10-10 | 2015-07-28 | Asahi Kasei Chemicals Corp | Metodos de produção de tereftalato de polialquileno, de produção de um artigo moldado de tereftalato de polialquileno, artigo moldado de tereftalato de polialquileno, tereftalato de polietileno, e artigo moldado de tereftalato de polietileno |
| US7256228B2 (en) | 2003-11-21 | 2007-08-14 | General Electric Company | Stabilized polycarbonate polyester composition |
| US20050137304A1 (en) | 2003-12-18 | 2005-06-23 | Strand Marc A. | Process for calendering of polyesters |
| US7354653B2 (en) | 2003-12-18 | 2008-04-08 | Eastman Chemical Company | High clarity films with improved thermal properties |
| US7241838B2 (en) | 2003-12-19 | 2007-07-10 | Eastman Chemical Company | Blends of aliphatic-aromatic copolyesters with ethylene-vinyl acetate copolymers |
| US7368511B2 (en) | 2003-12-22 | 2008-05-06 | Eastman Chemical Company | Polymer blends with improved rheology and improved unnotched impact strength |
| US7368503B2 (en) | 2003-12-22 | 2008-05-06 | Eastman Chemical Company | Compatibilized blends of biodegradable polymers with improved rheology |
| US7160977B2 (en) | 2003-12-22 | 2007-01-09 | Eastman Chemical Company | Polymer blends with improved notched impact strength |
| US7807745B2 (en) | 2006-01-27 | 2010-10-05 | Sabic Innovative Plastics Ip B.V. | Molding compositions containing polycarbonate and modified polybutylene terephthalate (PBT) random copolymers derived from polyethylene terephthalate (PET) |
| US7157139B2 (en) | 2004-04-19 | 2007-01-02 | Grant W. Doney | Polymer manufacturing process |
| CA2565725A1 (en) | 2004-05-25 | 2005-12-08 | Novamont S.P.A. | Perforated biodegradable films and sanitary products obtained therefrom |
| ITMI20041150A1 (it) | 2004-06-09 | 2004-09-09 | Novamont Spa | Processo perla produzione di film biodegradabili aventi migliorate proprieta' meccaniche |
| US20060004151A1 (en) | 2004-06-30 | 2006-01-05 | General Electric Company | Copolymers containing indan moieties and blends thereof |
| US7129301B2 (en) | 2005-01-07 | 2006-10-31 | Far Eastern Textile Ltd. | Method for preparing a biodegradable copolyester |
| JPWO2006104013A1 (ja) | 2005-03-25 | 2008-09-04 | 三菱樹脂株式会社 | ポリ乳酸系カード基材およびカード |
| US7655746B2 (en) | 2005-09-16 | 2010-02-02 | Eastman Chemical Company | Phosphorus containing compounds for reducing acetaldehyde in polyesters polymers |
| EP1938854B1 (en) | 2005-09-28 | 2013-07-24 | Terumo Kabushiki Kaisha | Synthetic resin needles |
| US20070082982A1 (en) | 2005-10-11 | 2007-04-12 | The Procter & Gamble Company | Water stable compositions and articles comprising starch and methods of making the same |
| US20090169772A1 (en) | 2005-12-09 | 2009-07-02 | Konica Minolta Opto, Inc. | Retardation film, method for producing retardation film, polarizing plate and liquid crystal display |
| US7737246B2 (en) | 2005-12-15 | 2010-06-15 | Eastman Chemical Company | Polyester compositions which comprise cyclobutanediol, cyclohexanedimethanol, and ethylene glycol and manufacturing processes therefor |
| CA2626033C (en) | 2005-12-29 | 2013-09-03 | Bp Corporation North America Inc. | Ethanolysis of pet to form det and oxidation thereof |
| EP1994072A2 (en) | 2006-01-27 | 2008-11-26 | General Electric Company | Molding compositions containing polyalkylene terephthalates and modified polybutylene terephthalate (pbt) random copolymers derived from pet |
| ATE453681T1 (de) | 2006-01-27 | 2010-01-15 | Gen Electric | Artikel aus zusammensetzungen mit modifizierten polybutylen-terephthalat-statistik-copolymeren aus polyethylen-terephthalat |
| US7902263B2 (en) | 2006-01-27 | 2011-03-08 | Sabic Innovative Plastics Ip B.V. | Process for making polybutylene terephthalate (PBT) from polyethylene terephthalate (PET) |
| US8680167B2 (en) | 2006-01-27 | 2014-03-25 | Sabic Innovative Plastics Ip B.V. | Molding compositions containing fillers and modified polybutylene terephthalate (PBT) random copolymers derived from polyethylene terephthalate (PET) |
| US7799836B2 (en) | 2006-03-01 | 2010-09-21 | Sabic Innovative Plastics Ip B.V. | Process for making polybutylene terephthalate (PBT) from polyethylene terephthalate (PET) |
| DE102006015941A1 (de) * | 2006-04-05 | 2007-10-11 | Mitsubishi Polyester Film Gmbh | Mehrschichtige, weiße Polyesterfolie |
| TWI402293B (zh) | 2006-04-06 | 2013-07-21 | Teijin Fibers Ltd | Production method of polyethylene terephthalate |
| US20080081898A1 (en) | 2006-10-02 | 2008-04-03 | Ross Jeffrey S | Polyester fiber compositions |
| US20080242751A1 (en) | 2006-12-27 | 2008-10-02 | Kurian Joseph V | Processes for manufacturing polyesters from post-consumer polyester |
| JP5239448B2 (ja) | 2007-06-04 | 2013-07-17 | 東レ株式会社 | 帯電防止性白色ポリエステルフィルム |
| CN101392073B (zh) | 2007-09-18 | 2012-03-21 | 宏力生化科技股份有限公司 | 全生分解性淀粉树脂及其制法与薄膜制品及用以制备该淀粉树脂的树脂组合物 |
| US7799892B2 (en) | 2008-05-02 | 2010-09-21 | Sabic Innovative Plastics Ip B.V. | Method of making polybutylene terephthalate and compositions and articles comprising the same |
| CN102112561A (zh) | 2008-07-29 | 2011-06-29 | 巴斯夫欧洲公司 | 水性通用颜料糊 |
| US20100041831A1 (en) | 2008-08-15 | 2010-02-18 | Bayer Materialscience Llc | Impact modified polycarbonate-polylactic acid composition |
| JP5326741B2 (ja) * | 2008-09-29 | 2013-10-30 | 東レ株式会社 | ポリエステル重合触媒およびそれを用いるポリエステルの製造方法 |
| CN105218794A (zh) | 2008-09-29 | 2016-01-06 | 巴斯夫欧洲公司 | 脂族聚酯 |
| WO2010077809A1 (en) | 2008-12-15 | 2010-07-08 | E. I. Du Pont De Nemours And Company | Copolyesters with enhanced tear strength |
| US20100168317A1 (en) | 2008-12-30 | 2010-07-01 | Cahoon-Brister Kristen | Poly(butylene terephthalate) compositions, methods of manufacture, and articles thereof |
| US20100168371A1 (en) | 2008-12-31 | 2010-07-01 | Corrado Berti | Bio-Based Terephthalate Polyesters |
| US7910657B2 (en) | 2008-12-30 | 2011-03-22 | Sabic Innovative Plastics Ip B.V. | Process for the manufacture of polybutylene terephthalate copolymers from polyethylene terephthalate, and compositions and articles thereof |
| US8796356B2 (en) * | 2009-09-23 | 2014-08-05 | Sabic Innovative Plastics Ip B.V. | Biodegradable aliphatic-aromatic copolyesters, methods of manufacture, and articles thereof |
| EP2499189B1 (de) | 2009-11-09 | 2015-01-07 | Basf Se | Verfahren zur herstellung von schrumpffolien |
| KR20130106272A (ko) | 2010-04-30 | 2013-09-27 | 제이에스알 가부시끼가이샤 | 필름, 수지 조성물 및 중합체 |
| US8933162B2 (en) | 2011-07-15 | 2015-01-13 | Saudi Basic Industries Corporation | Color-stabilized biodegradable aliphatic-aromatic copolyesters, methods of manufacture, and articles thereof |
| US8946345B2 (en) | 2011-08-30 | 2015-02-03 | Saudi Basic Industries Corporation | Method for the preparation of (polybutylene-co-adipate terephthalate) through the in situ phosphorus containing titanium based catalyst |
-
2011
- 2011-07-15 US US13/183,807 patent/US8877862B2/en not_active Expired - Fee Related
-
2012
- 2012-07-13 AU AU2012284304A patent/AU2012284304B2/en not_active Expired - Fee Related
- 2012-07-13 WO PCT/US2012/046625 patent/WO2013012705A1/en not_active Ceased
- 2012-07-13 EP EP12738342.0A patent/EP2731980B1/en not_active Not-in-force
- 2012-07-13 CN CN201280034695.4A patent/CN103703049B/zh not_active Expired - Fee Related
- 2012-07-13 JP JP2014520355A patent/JP2014524958A/ja active Pending
-
2014
- 2014-10-31 US US14/529,651 patent/US20150057400A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007314743A (ja) * | 2006-04-27 | 2007-12-06 | Seiko Pmc Corp | ポリエステル系樹脂の製造方法、及びその製造方法により得られたポリエステル系樹脂、並びに該樹脂を用いたトナー用樹脂 |
| JP2011093986A (ja) * | 2009-10-28 | 2011-05-12 | Nippon Ester Co Ltd | ポリエステルの製造方法及びポリエステル |
| JP2014520933A (ja) * | 2011-07-15 | 2014-08-25 | サウディ ベーシック インダストリーズ コーポレイション | 色が安定な生分解性脂肪族/芳香族共重合ポリエステル、製造方法、及びその物品 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020535286A (ja) * | 2017-09-28 | 2020-12-03 | フラウンホーファー−ゲゼルシャフト ツゥア フェアデルング デア アンゲヴァンドテン フォァシュング エー.ファウ. | ハロゲンフリー熱可塑性リサイクル材を安定化するための方法、安定化プラスチック組成物、ならびにそれから生成される成形コンパウンドおよび成形部品 |
| US11591450B2 (en) | 2017-09-28 | 2023-02-28 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Method for stabilizing halogen-free thermoplastic recyclates, stabilized plastic compositions, and molding compounds and molded parts produced therefrom |
| JP2023535882A (ja) * | 2020-07-06 | 2023-08-22 | アクアパック ポリマーズ リミテッド | ポリビニルアルコールの製造方法及びその製造装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| US8877862B2 (en) | 2014-11-04 |
| US20130018142A1 (en) | 2013-01-17 |
| AU2012284304B2 (en) | 2015-05-07 |
| EP2731980B1 (en) | 2017-04-12 |
| CN103703049A (zh) | 2014-04-02 |
| EP2731980A1 (en) | 2014-05-21 |
| CN103703049B (zh) | 2016-04-06 |
| US20150057400A1 (en) | 2015-02-26 |
| WO2013012705A1 (en) | 2013-01-24 |
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