KR20110110184A - 지방족-방향족 코폴리에테르에스테르의 중합 - Google Patents
지방족-방향족 코폴리에테르에스테르의 중합 Download PDFInfo
- Publication number
- KR20110110184A KR20110110184A KR1020117016358A KR20117016358A KR20110110184A KR 20110110184 A KR20110110184 A KR 20110110184A KR 1020117016358 A KR1020117016358 A KR 1020117016358A KR 20117016358 A KR20117016358 A KR 20117016358A KR 20110110184 A KR20110110184 A KR 20110110184A
- Authority
- KR
- South Korea
- Prior art keywords
- aliphatic
- aromatic
- sodium
- component
- acid
- 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.)
- Withdrawn
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- 238000006116 polymerization reaction Methods 0.000 title abstract description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 122
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 58
- 239000000203 mixture Substances 0.000 claims abstract description 56
- -1 glycol ethers Chemical class 0.000 claims abstract description 49
- 229920000642 polymer Polymers 0.000 claims abstract description 49
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 55
- 239000011734 sodium Substances 0.000 claims description 55
- 229910052708 sodium Inorganic materials 0.000 claims description 49
- 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 47
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 36
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 35
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 35
- 239000000872 buffer Substances 0.000 claims description 33
- 239000011541 reaction mixture Substances 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
- 150000001875 compounds Chemical class 0.000 claims description 31
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 23
- 239000000178 monomer Substances 0.000 claims description 23
- 238000003756 stirring Methods 0.000 claims description 23
- 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
- 150000002148 esters Chemical class 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000001931 aliphatic 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
- 235000017281 sodium acetate Nutrition 0.000 claims description 12
- 239000010936 titanium Substances 0.000 claims description 12
- 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
- 238000010438 heat treatment Methods 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
- 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
- 239000004280 Sodium formate Substances 0.000 claims description 5
- 239000001632 sodium acetate Substances 0.000 claims description 5
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 5
- 239000004299 sodium benzoate Substances 0.000 claims description 5
- 235000010234 sodium benzoate Nutrition 0.000 claims description 5
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 5
- 235000019254 sodium formate Nutrition 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
- 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
- 239000000835 fiber Substances 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 3
- LLHSEQCZSNZLRI-UHFFFAOYSA-M sodium;3,5-bis(methoxycarbonyl)benzenesulfonate Chemical group [Na+].COC(=O)C1=CC(C(=O)OC)=CC(S([O-])(=O)=O)=C1 LLHSEQCZSNZLRI-UHFFFAOYSA-M 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 2
- 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 13
- 150000002334 glycols Chemical class 0.000 abstract description 12
- 239000000539 dimer Substances 0.000 abstract description 7
- 230000018044 dehydration Effects 0.000 abstract description 4
- 238000006297 dehydration reaction Methods 0.000 abstract description 4
- 230000000930 thermomechanical effect Effects 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 52
- 229940035437 1,3-propanediol Drugs 0.000 description 34
- 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
- 238000004821 distillation Methods 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 14
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 238000006471 dimerization reaction Methods 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 229920001634 Copolyester Polymers 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229920002678 cellulose Polymers 0.000 description 9
- 238000000113 differential scanning calorimetry Methods 0.000 description 9
- 239000001913 cellulose Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- 230000009477 glass transition Effects 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 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
- 235000011089 carbon dioxide Nutrition 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 239000004810 polytetrafluoroethylene Substances 0.000 description 6
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000006085 branching agent Substances 0.000 description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 5
- 230000001276 controlling effect Effects 0.000 description 5
- 229920000554 ionomer Polymers 0.000 description 5
- 239000002667 nucleating agent Substances 0.000 description 5
- 239000004970 Chain extender Substances 0.000 description 4
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 238000006473 carboxylation reaction Methods 0.000 description 4
- 238000009264 composting Methods 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- 229920000591 gum Polymers 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
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- 238000002156 mixing Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
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- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 description 2
- XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 2
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- 238000002835 absorbance Methods 0.000 description 2
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- 150000008065 acid anhydrides Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
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- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
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- CAKVXHUYTFYBPK-UHFFFAOYSA-N bis(2-hydroxyethyl) benzene-1,2-dicarboxylate Chemical compound OCCOC(=O)C1=CC=CC=C1C(=O)OCCO CAKVXHUYTFYBPK-UHFFFAOYSA-N 0.000 description 2
- ULCGAWLDXLEIIR-UHFFFAOYSA-N bis(2-hydroxyethyl) benzene-1,3-dicarboxylate Chemical compound OCCOC(=O)C1=CC=CC(C(=O)OCCO)=C1 ULCGAWLDXLEIIR-UHFFFAOYSA-N 0.000 description 2
- QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 description 2
- VOFBNVWLHPRAHN-UHFFFAOYSA-N bis(3-hydroxypropyl) benzene-1,2-dicarboxylate Chemical compound OCCCOC(=O)C1=CC=CC=C1C(=O)OCCCO VOFBNVWLHPRAHN-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- B32B1/00—Layered products having a non-planar shape
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- 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
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- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
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- C08G63/6886—Dicarboxylic acids and dihydroxy compounds
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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
- C08G63/78—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
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- 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
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- C08L3/02—Starch; Degradation products thereof, e.g. dextrin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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- 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
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- 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
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- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
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- 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
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- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
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Landscapes
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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| 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 |
| US10218702B2 (en) | 2015-11-09 | 2019-02-26 | Silvercar, Inc. | Vehicle access systems and methods |
| EP4612212A1 (en) | 2022-11-04 | 2025-09-10 | Clariant International Ltd | Polyesters |
| CN120322480A (zh) | 2022-11-04 | 2025-07-15 | 宝洁公司 | 织物和家庭护理组合物 |
| EP4612208A1 (en) | 2022-11-04 | 2025-09-10 | Clariant International Ltd | Polyesters |
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| 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 |
| DK0809666T4 (da) | 1995-02-16 | 2002-12-02 | Basf Ag | Biologisk nedbrydelige polymerer, fremgangsmåder til deres fremstilling samt deres anvendelse til fremstilling af bionedbrydelige formlegemer |
| 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 |
| DE602004028359D1 (de) | 2003-05-06 | 2010-09-09 | Du Pont | Reinigung von biologisch produziertem 1,3-propandiol |
| JP4908218B2 (ja) | 2003-05-06 | 2012-04-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 生化学的に誘導された１，３−プロパンジオールの水素化 |
| US7084311B2 (en) | 2003-05-06 | 2006-08-01 | E. I. Du Pont De Nemours And Company | Hydrogenation of chemically derived 1,3-propanediol |
| 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 |
| ATE440911T1 (de) * | 2004-07-20 | 2009-09-15 | Solotex Corp | Polytrimethylenterephthalat |
| 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 KR KR1020117016358A patent/KR20110110184A/ko not_active Withdrawn
- 2009-12-14 US US13/128,920 patent/US20110229674A1/en not_active Abandoned
- 2009-12-14 WO PCT/US2009/067875 patent/WO2010075030A1/en not_active Ceased
- 2009-12-14 US US13/127,067 patent/US20110206883A1/en not_active Abandoned
- 2009-12-14 EP EP09768595A patent/EP2365992A1/en not_active Withdrawn
- 2009-12-14 CN CN2009801505034A patent/CN102245671A/zh active Pending
- 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 AU AU2009330405A patent/AU2009330405A1/en not_active Abandoned
- 2009-12-14 JP JP2011540951A patent/JP2012512279A/ja not_active Abandoned
-
2012
- 2012-12-28 US US13/729,787 patent/US20130129951A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP2358783A1 (en) | 2011-08-24 |
| EP2365992A1 (en) | 2011-09-21 |
| WO2010075030A1 (en) | 2010-07-01 |
| AU2009330405A1 (en) | 2010-07-01 |
| AU2009330405A2 (en) | 2011-05-19 |
| WO2010071771A1 (en) | 2010-06-24 |
| US20110206883A1 (en) | 2011-08-25 |
| JP2012512279A (ja) | 2012-05-31 |
| CN102245671A (zh) | 2011-11-16 |
| US20110229674A1 (en) | 2011-09-22 |
| US20130129951A1 (en) | 2013-05-23 |
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| PA0105 | International application |
Patent event date: 20110714 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |