AU2009330626A1 - (Meth)acrylic esters of poly(trimethylene ether) glycol and uses thereof - Google Patents
(Meth)acrylic esters of poly(trimethylene ether) glycol and uses thereof Download PDFInfo
- Publication number
- AU2009330626A1 AU2009330626A1 AU2009330626A AU2009330626A AU2009330626A1 AU 2009330626 A1 AU2009330626 A1 AU 2009330626A1 AU 2009330626 A AU2009330626 A AU 2009330626A AU 2009330626 A AU2009330626 A AU 2009330626A AU 2009330626 A1 AU2009330626 A1 AU 2009330626A1
- Authority
- AU
- Australia
- Prior art keywords
- acrylate
- glycol
- poly
- trimethylene ether
- meth
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 121
- -1 poly(trimethylene ether) Polymers 0.000 title claims description 90
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 57
- 229920000163 poly(trimethylene ether) Polymers 0.000 title claims description 41
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 29
- 238000000034 method Methods 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 35
- 230000008569 process Effects 0.000 claims description 35
- 239000000463 material Substances 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000003999 initiator Substances 0.000 claims description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 6
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 3
- LMAUULKNZLEMGN-UHFFFAOYSA-N 1-ethyl-3,5-dimethylbenzene Chemical compound CCC1=CC(C)=CC(C)=C1 LMAUULKNZLEMGN-UHFFFAOYSA-N 0.000 claims description 3
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 3
- JGRXEBOFWPLEAV-UHFFFAOYSA-N 2-ethylbutyl prop-2-enoate Chemical compound CCC(CC)COC(=O)C=C JGRXEBOFWPLEAV-UHFFFAOYSA-N 0.000 claims description 3
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- VEPKQEUBKLEPRA-UHFFFAOYSA-N VX-745 Chemical compound FC1=CC(F)=CC=C1SC1=NN2C=NC(=O)C(C=3C(=CC=CC=3Cl)Cl)=C2C=C1 VEPKQEUBKLEPRA-UHFFFAOYSA-N 0.000 claims description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims description 3
- IQRVNLYKJBNWHE-UHFFFAOYSA-N heptan-2-yl prop-2-enoate Chemical compound CCCCCC(C)OC(=O)C=C IQRVNLYKJBNWHE-UHFFFAOYSA-N 0.000 claims description 3
- SCFQUKBBGYTJNC-UHFFFAOYSA-N heptyl prop-2-enoate Chemical compound CCCCCCCOC(=O)C=C SCFQUKBBGYTJNC-UHFFFAOYSA-N 0.000 claims description 3
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 3
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002978 peroxides Chemical group 0.000 claims description 3
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 150000002432 hydroperoxides Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 239000004745 nonwoven fabric Substances 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 1
- 229910010293 ceramic material Inorganic materials 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- WYMSBXTXOHUIGT-UHFFFAOYSA-N paraoxon Chemical compound CCOP(=O)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 WYMSBXTXOHUIGT-UHFFFAOYSA-N 0.000 claims 1
- 239000012966 redox initiator Substances 0.000 claims 1
- 239000002759 woven fabric Substances 0.000 claims 1
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 40
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 40
- 229940035437 1,3-propanediol Drugs 0.000 description 40
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 239000000047 product Substances 0.000 description 27
- 238000005886 esterification reaction Methods 0.000 description 23
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 230000032050 esterification Effects 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000003377 acid catalyst Substances 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000005690 diesters Chemical class 0.000 description 7
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 7
- 238000006068 polycondensation reaction Methods 0.000 description 7
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- 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
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 230000007613 environmental effect Effects 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- 238000006473 carboxylation reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000004386 diacrylate group Chemical group 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 230000000243 photosynthetic effect Effects 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229920006397 acrylic thermoplastic Polymers 0.000 description 3
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- 239000012467 final product Substances 0.000 description 3
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- 238000005259 measurement Methods 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 3
- 239000012925 reference material Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
-
- 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
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
-
- 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
- C08F22/00—Homopolymers and 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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/10—Esters
-
- 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
- C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/4935—Impregnated naturally solid product [e.g., leather, stone, etc.]
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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
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/30—Woven fabric [i.e., woven strand or strip material]
-
- 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
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/60—Nonwoven fabric [i.e., nonwoven strand or fiber material]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyethers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14024208P | 2008-12-23 | 2008-12-23 | |
| US61/140,242 | 2008-12-23 | ||
| PCT/US2009/062306 WO2010074806A1 (en) | 2008-12-23 | 2009-10-28 | (meth)acrylic esters of poly(trimethylene ether) glycol and uses thereof |
Publications (1)
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| AU2009330626A1 true AU2009330626A1 (en) | 2010-07-01 |
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| US (1) | US8198360B2 (https=) |
| EP (1) | EP2370483B1 (https=) |
| JP (1) | JP2012513525A (https=) |
| KR (1) | KR20110104975A (https=) |
| CN (1) | CN102264781A (https=) |
| AU (1) | AU2009330626A1 (https=) |
| BR (1) | BRPI0914407A2 (https=) |
| CA (1) | CA2739620A1 (https=) |
| MX (1) | MX2011006738A (https=) |
| TW (1) | TW201026724A (https=) |
| WO (1) | WO2010074806A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20130289129A1 (en) * | 2010-11-10 | 2013-10-31 | Us Coatings Ip Co Llc | Radiation curable coating composition containing low molecular weight polytrimethylene ether glycol |
| WO2012150467A2 (en) * | 2011-05-04 | 2012-11-08 | The University Of Nottingham | Novel polymers which resist bacterial attachment |
| US20130184408A1 (en) * | 2012-01-17 | 2013-07-18 | E I Du Pont De Nemours And Company | Use of low molecular weight polytrimethylene ether glycol as a polymerization solvent |
| CN103865055B (zh) * | 2014-03-19 | 2016-03-23 | 上海应用技术学院 | 一种大分子疏水性单体聚四氢呋喃二丙烯酸酯及其制备方法 |
| CN104530301B (zh) * | 2014-12-04 | 2016-01-27 | 佛山市高明同德化工有限公司 | 一种高韧性高温碳化不残留的热塑性丙烯酸树脂及其制备方法 |
| EP3601442A1 (en) | 2017-03-28 | 2020-02-05 | Arkema France | Compositions useful for forming soft touch coatings |
| KR102272234B1 (ko) * | 2020-09-25 | 2021-07-02 | 주식회사 대양포리졸 | 히트 실링, 안티블로킹성 등을 만족하는 종이용 수성 코팅 조성물 |
| 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 |
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| JP2730770B2 (ja) * | 1989-04-28 | 1998-03-25 | 株式会社日本触媒 | セメント混和剤 |
| US5098973A (en) * | 1989-05-24 | 1992-03-24 | Sumitomo Rubber Industries Ltd. | Hardening resin composition |
| JP2992325B2 (ja) * | 1990-10-26 | 1999-12-20 | 三菱レイヨン株式会社 | ポリブチレングリコールジ（メタ）アクリレート及びそれを含む注型重合用樹脂組成物 |
| JPH04233981A (ja) * | 1990-11-30 | 1992-08-21 | Toyo Ink Mfg Co Ltd | 水性印刷インキ |
| JPH05331499A (ja) * | 1992-05-29 | 1993-12-14 | Lion Corp | 皮革処理剤 |
| DE4222708A1 (de) | 1992-07-10 | 1994-01-13 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| JP2000144031A (ja) * | 1994-04-20 | 2000-05-26 | Citizen Watch Co Ltd | 記録液 |
| 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 |
| CN1297347A (zh) * | 1998-02-19 | 2001-05-30 | 奥拉修蒂科有限公司 | 抗菌托牙粘合剂组合物 |
| JP2000226419A (ja) * | 1998-11-30 | 2000-08-15 | Pola Chem Ind Inc | 表面改質用の共重合体 |
| WO2000079312A1 (en) * | 1999-06-17 | 2000-12-28 | Bausch & Lomb Surgical, Inc. | High refractive index compositions for ophthalmic implants |
| 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 |
| US6977291B2 (en) | 1999-12-17 | 2005-12-20 | E.I. Du Pont De Nemours And Company | Production of polytrimethylene ether glycol and copolymers thereof |
| 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 |
| US6465397B1 (en) | 2000-02-11 | 2002-10-15 | Clariant Finance (Bvi) Limited | Synthetic crosslinked copolymer solutions and direct injection to subterranean oil and gas formations |
| US20040030095A1 (en) | 2002-08-09 | 2004-02-12 | Sunkara Hari B. | Poly(trimethylene-ethylene ether) glycols |
| 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 |
| EP1866357B1 (en) | 2005-03-15 | 2012-02-22 | Showa Denko K.K. | (meth)acryloyl group-containing aromatic isocyanate compound and production process thereof |
| US20080108845A1 (en) * | 2006-11-07 | 2008-05-08 | Hari Babu Sunkara | Polytrimethylene ether glycol esters |
| US8063161B2 (en) | 2007-04-16 | 2011-11-22 | Designer Molecules, Inc. | Low temperature curing acrylate and maleimide based formulations and methods for use thereof |
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2009
- 2009-10-28 BR BRPI0914407A patent/BRPI0914407A2/pt not_active IP Right Cessation
- 2009-10-28 CA CA 2739620 patent/CA2739620A1/en not_active Abandoned
- 2009-10-28 EP EP09744296.6A patent/EP2370483B1/en not_active Not-in-force
- 2009-10-28 KR KR1020117017206A patent/KR20110104975A/ko not_active Withdrawn
- 2009-10-28 CN CN2009801521412A patent/CN102264781A/zh active Pending
- 2009-10-28 US US12/607,193 patent/US8198360B2/en not_active Expired - Fee Related
- 2009-10-28 MX MX2011006738A patent/MX2011006738A/es not_active Application Discontinuation
- 2009-10-28 WO PCT/US2009/062306 patent/WO2010074806A1/en not_active Ceased
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- 2009-10-28 AU AU2009330626A patent/AU2009330626A1/en not_active Abandoned
- 2009-10-28 TW TW98136513A patent/TW201026724A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012513525A (ja) | 2012-06-14 |
| EP2370483B1 (en) | 2014-07-16 |
| MX2011006738A (es) | 2011-07-13 |
| CA2739620A1 (en) | 2010-07-01 |
| BRPI0914407A2 (pt) | 2015-10-20 |
| US20100159767A1 (en) | 2010-06-24 |
| CN102264781A (zh) | 2011-11-30 |
| WO2010074806A1 (en) | 2010-07-01 |
| EP2370483A1 (en) | 2011-10-05 |
| US8198360B2 (en) | 2012-06-12 |
| KR20110104975A (ko) | 2011-09-23 |
| TW201026724A (en) | 2010-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |