KR20110114599A - 폴리(트라이메틸렌 에테르) 글리콜의 아크릴산 및 메타크릴산 에스테르의 제조 방법 - Google Patents
폴리(트라이메틸렌 에테르) 글리콜의 아크릴산 및 메타크릴산 에스테르의 제조 방법 Download PDFInfo
- Publication number
- KR20110114599A KR20110114599A KR1020117017205A KR20117017205A KR20110114599A KR 20110114599 A KR20110114599 A KR 20110114599A KR 1020117017205 A KR1020117017205 A KR 1020117017205A KR 20117017205 A KR20117017205 A KR 20117017205A KR 20110114599 A KR20110114599 A KR 20110114599A
- Authority
- KR
- South Korea
- Prior art keywords
- glycol
- poly
- acrylic acid
- meth
- trimethylene ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 114
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 229920000163 poly(trimethylene ether) Polymers 0.000 title claims abstract description 42
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title description 19
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title description 12
- 125000005397 methacrylic acid ester group Chemical group 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 47
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 33
- 230000008569 process Effects 0.000 claims abstract description 15
- -1 polytrimethylene Polymers 0.000 claims description 53
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 43
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 43
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 40
- 238000005886 esterification reaction Methods 0.000 claims description 26
- 230000032050 esterification Effects 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 15
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- 239000000178 monomer Substances 0.000 claims description 14
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 claims description 3
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- 125000003118 aryl group Chemical group 0.000 claims description 2
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- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
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- 239000007858 starting material Substances 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 6
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- 238000003786 synthesis reaction Methods 0.000 description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000243 photosynthetic effect Effects 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
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- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 3
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- IQRVNLYKJBNWHE-UHFFFAOYSA-N heptan-2-yl prop-2-enoate Chemical compound CCCCCC(C)OC(=O)C=C IQRVNLYKJBNWHE-UHFFFAOYSA-N 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- SCFQUKBBGYTJNC-UHFFFAOYSA-N heptyl prop-2-enoate Chemical compound CCCCCCCOC(=O)C=C SCFQUKBBGYTJNC-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002307 isotope ratio mass spectrometry Methods 0.000 description 1
- 229940039696 lactobacillus Drugs 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002735 metacrylic acids Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 230000012223 nuclear import Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- 229950006800 prenderol Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006126 semicrystalline polymer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000005219 trimethyl ethers Chemical class 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers 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
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14023808P | 2008-12-23 | 2008-12-23 | |
| US61/140,238 | 2008-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20110114599A true KR20110114599A (ko) | 2011-10-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020117017205A Withdrawn KR20110114599A (ko) | 2008-12-23 | 2009-10-28 | 폴리(트라이메틸렌 에테르) 글리콜의 아크릴산 및 메타크릴산 에스테르의 제조 방법 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8207372B2 (https=) |
| EP (1) | EP2370499B1 (https=) |
| JP (1) | JP2012513524A (https=) |
| KR (1) | KR20110114599A (https=) |
| CN (1) | CN102264797A (https=) |
| AU (1) | AU2009330625A1 (https=) |
| BR (1) | BRPI0914378A2 (https=) |
| CA (1) | CA2739566A1 (https=) |
| MX (1) | MX2011006737A (https=) |
| TW (1) | TW201024325A (https=) |
| WO (1) | WO2010074805A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4638612A1 (en) | 2022-12-22 | 2025-10-29 | Allnex Belgium, S.A. | Actinic radiation curable coating composition comprising biobased monomer |
| EP4705364A1 (en) | 2023-05-05 | 2026-03-11 | Allnex Belgium, S.A. | A biobased radical curable composition for forming solid objects |
| CN121127508A (zh) | 2023-05-05 | 2025-12-12 | 湛新比利时股份有限公司 | 用于涂料的生物基可自由基固化的组合物 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2892820A (en) * | 1956-03-29 | 1959-06-30 | California Research Corp | Oil soluble polymers containing polyalkylene glycol side-chains |
| US4038264A (en) * | 1974-01-07 | 1977-07-26 | National Patent Development Corporation | Hema copolymers having high oxygen permeability |
| ES2077811T3 (es) * | 1990-11-09 | 1995-12-01 | Nippon Catalytic Chem Ind | Inhibidor de polimerizacion y metodo de inhibicion de polimerizacion para un compuesto de vinilo. |
| DE4222708A1 (de) * | 1992-07-10 | 1994-01-13 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| 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 |
| FR2797265B1 (fr) * | 1999-08-02 | 2004-06-18 | Essilor Int | Compositions polymerisables pour la fabrication de substrats polymeres transparents, substrats polymeres transparents obtenus et leurs applications dans l'optique |
| CN1238317C (zh) * | 1999-12-17 | 2006-01-25 | 纳幕尔杜邦公司 | 制备聚三亚甲基醚二醇的连续方法 |
| US6977291B2 (en) * | 1999-12-17 | 2005-12-20 | E.I. Du Pont De Nemours And Company | Production of polytrimethylene ether glycol and copolymers thereof |
| DE10125237A1 (de) * | 2001-05-22 | 2002-11-28 | Basf Ag | Wasserlösliche Polymerisate von Estern aus Acrylsäure und Alkylpolyalkylenglykolen |
| CN1435823A (zh) * | 2002-02-01 | 2003-08-13 | 日本胜利株式会社 | 光盘 |
| US20040030095A1 (en) * | 2002-08-09 | 2004-02-12 | Sunkara Hari B. | Poly(trimethylene-ethylene ether) glycols |
| US20040225107A1 (en) * | 2003-05-06 | 2004-11-11 | Sunkara Hari Babu | Polytrimethylene ether glycol with excellent quality from biochemically-derived 1,3-propanediol |
| US7323539B2 (en) * | 2003-05-06 | 2008-01-29 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether glycol and polytrimethylene ether ester with excellent quality |
| US7084311B2 (en) * | 2003-05-06 | 2006-08-01 | E. I. Du Pont De Nemours And Company | Hydrogenation of chemically derived 1,3-propanediol |
| DE10331450A1 (de) | 2003-07-10 | 2005-01-27 | Basf Ag | (Meth)acrylsäureester monoalkoxilierter Polyole und deren Herstellung |
| US6972143B2 (en) | 2003-10-27 | 2005-12-06 | Kyle Baldwin | Protective U.V. curable cover layer for optical media |
| US20080108845A1 (en) | 2006-11-07 | 2008-05-08 | Hari Babu Sunkara | Polytrimethylene ether glycol esters |
| US20100069532A1 (en) * | 2006-12-08 | 2010-03-18 | Basf Se | Process for preparing polymerizable carboxylic esters with alkoxy groups |
-
2009
- 2009-10-28 WO PCT/US2009/062287 patent/WO2010074805A1/en not_active Ceased
- 2009-10-28 US US12/607,157 patent/US8207372B2/en not_active Expired - Fee Related
- 2009-10-28 EP EP09741178A patent/EP2370499B1/en not_active Not-in-force
- 2009-10-28 BR BRPI0914378A patent/BRPI0914378A2/pt not_active IP Right Cessation
- 2009-10-28 KR KR1020117017205A patent/KR20110114599A/ko not_active Withdrawn
- 2009-10-28 CN CN2009801523371A patent/CN102264797A/zh active Pending
- 2009-10-28 JP JP2011543517A patent/JP2012513524A/ja active Pending
- 2009-10-28 TW TW098136509A patent/TW201024325A/zh unknown
- 2009-10-28 MX MX2011006737A patent/MX2011006737A/es unknown
- 2009-10-28 AU AU2009330625A patent/AU2009330625A1/en not_active Abandoned
- 2009-10-28 CA CA2739566A patent/CA2739566A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012513524A (ja) | 2012-06-14 |
| CA2739566A1 (en) | 2010-07-01 |
| MX2011006737A (es) | 2011-07-13 |
| US20100160672A1 (en) | 2010-06-24 |
| CN102264797A (zh) | 2011-11-30 |
| US8207372B2 (en) | 2012-06-26 |
| EP2370499A1 (en) | 2011-10-05 |
| AU2009330625A1 (en) | 2010-07-01 |
| TW201024325A (en) | 2010-07-01 |
| EP2370499B1 (en) | 2012-11-28 |
| BRPI0914378A2 (pt) | 2015-10-20 |
| WO2010074805A1 (en) | 2010-07-01 |
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| KR20110013451A (ko) | 폴리(트라이메틸렌 에테르) 글리콜 에스테르를 포함하는 가소제 | |
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Legal Events
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| PA0105 | International application |
Patent event date: 20110722 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| 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 |