ES2684999T3 - Método de fabricación de un polímero ramificado, un polímero ramificado y usos de un polímero de este tipo - Google Patents
Método de fabricación de un polímero ramificado, un polímero ramificado y usos de un polímero de este tipo Download PDFInfo
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- ES2684999T3 ES2684999T3 ES15718376.5T ES15718376T ES2684999T3 ES 2684999 T3 ES2684999 T3 ES 2684999T3 ES 15718376 T ES15718376 T ES 15718376T ES 2684999 T3 ES2684999 T3 ES 2684999T3
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- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- GCZZMHHPTUKDQE-UHFFFAOYSA-N pent-2-en-3-yl acetate Chemical compound CCC(=CC)OC(C)=O GCZZMHHPTUKDQE-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- IKUJAIDSWVXUGG-UHFFFAOYSA-N prop-1-enyl acetate Chemical compound CC=COC(C)=O IKUJAIDSWVXUGG-UHFFFAOYSA-N 0.000 description 1
- AOJIRGQJECGWRU-UHFFFAOYSA-N prop-1-enyl propanoate Chemical compound CCC(=O)OC=CC AOJIRGQJECGWRU-UHFFFAOYSA-N 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 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
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-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
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- WUCQRXWCJPCWTQ-UHFFFAOYSA-N trans-3-pentenal Natural products CC=CCC=O WUCQRXWCJPCWTQ-UHFFFAOYSA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- PIAOXUVIBAKVSP-UHFFFAOYSA-N γ-hydroxybutyraldehyde Chemical compound OCCCC=O PIAOXUVIBAKVSP-UHFFFAOYSA-N 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
- C08F16/00—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/02—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an alcohol radical
- C08F16/04—Acyclic compounds
- C08F16/06—Polyvinyl alcohol ; Vinyl alcohol
-
- 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
- C08F218/00—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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
- C08F218/08—Vinyl acetate
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F14/00—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 halogen
- C08F14/02—Monomers containing chlorine
- C08F14/04—Monomers containing two carbon atoms
- C08F14/06—Vinyl chloride
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/20—Aqueous medium with the aid of macromolecular dispersing agents
-
- 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
- C08F222/26—Esters of unsaturated alcohols
- C08F222/28—Diallyl maleate
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
-
- 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
- C08K5/07—Aldehydes; Ketones
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1405624.6A GB201405624D0 (en) | 2014-03-28 | 2014-03-28 | Method of making a branched polymer, a branched polymer and uses of such a polymer |
| GB201405624 | 2014-03-28 | ||
| PCT/GB2015/050937 WO2015145173A1 (en) | 2014-03-28 | 2015-03-27 | Method of making a branched polymer, a branched polymer and uses of such a polymer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2684999T3 true ES2684999T3 (es) | 2018-10-05 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15718376.5T Active ES2684999T3 (es) | 2014-03-28 | 2015-03-27 | Método de fabricación de un polímero ramificado, un polímero ramificado y usos de un polímero de este tipo |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10711073B2 (enExample) |
| EP (2) | EP3119815B1 (enExample) |
| JP (2) | JP7113617B2 (enExample) |
| KR (1) | KR102356385B1 (enExample) |
| CN (2) | CN109354641B (enExample) |
| BR (1) | BR112016022117A2 (enExample) |
| ES (1) | ES2684999T3 (enExample) |
| GB (1) | GB201405624D0 (enExample) |
| MX (1) | MX2016012327A (enExample) |
| RU (1) | RU2688179C2 (enExample) |
| TW (1) | TWI748930B (enExample) |
| WO (1) | WO2015145173A1 (enExample) |
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| WO2014049137A1 (en) | 2012-09-28 | 2014-04-03 | Saint-Gobain Performance Plastics Pampus Gmbh | Maintenance-free slide bearing with a combined adhesive sliding layer |
| ES2746157T3 (es) | 2015-03-05 | 2020-03-04 | Sekisui Specialty Chemicals Am | Dispersante de PVOH para polimerización de VCM |
| GB2580910A (en) | 2019-01-28 | 2020-08-05 | Synthomer Uk Ltd | Self-supported elastomeric film having self-healing properties made from a polymer latex |
| GB2580909A (en) | 2019-01-28 | 2020-08-05 | Synthomer Uk Ltd | Polymer latex and elastomeric film made therefrom having self-healing properties |
| GB201918030D0 (en) | 2019-12-09 | 2020-01-22 | Synthomer Uk Ltd | Improvements in, or relating to, binders and/or coatings |
| WO2023238674A1 (ja) * | 2022-06-08 | 2023-12-14 | デンカ株式会社 | ポリビニルアルコール系重合体 |
Family Cites Families (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2888442A (en) | 1954-04-09 | 1959-05-26 | Phillips Petroleum Co | New polymers from conjugated dienes and polyvinyl compounds prepared in the presence of mercaptans |
| GB967051A (en) | 1963-01-14 | 1964-08-19 | Du Pont | Microgels and coating compositions containing same |
| GB1068135A (en) * | 1964-03-04 | 1967-05-10 | Baker Chem Co J T | Suspension polymerization |
| DE1645624A1 (de) * | 1966-02-04 | 1970-12-17 | Vnii Sint Kaucuka Im Akademika | Verfahren zur Herstellung reaktionsfaehiger Synthesekautschuke |
| IL46681A (en) * | 1975-02-21 | 1977-06-30 | Imi Inst For Research And Dev | Interpolymers of vinyl chloride and their preparation |
| JPS51115587A (en) * | 1975-03-24 | 1976-10-12 | Kuraray Co Ltd | Method of producing polyvinylchloride resins |
| JPS5445686A (en) | 1977-08-11 | 1979-04-11 | Nippon Synthetic Chem Ind Co Ltd:The | Dispersion stabilizer for suspension polymerization of vinly compound |
| JPS5559241A (en) | 1978-10-09 | 1980-05-02 | Fuiritsupu Deii Supurangu | Constructed body |
| JPS5594978A (en) * | 1979-01-16 | 1980-07-18 | Unitika Chem Kk | Water-soluble or-dispersible hot melt adhesive |
| US4368275A (en) * | 1980-06-25 | 1983-01-11 | Asahi Kasei Kogyo Kabushiki Kaisha | Isocyanurate-vinyl alcohol-vinyl ester chromatographic packing |
| JPS57108662A (en) * | 1980-12-26 | 1982-07-06 | Asahi Chem Ind Co Ltd | Filler for high speed liquid chromatography |
| JPS5730945A (en) * | 1980-06-25 | 1982-02-19 | Asahi Chem Ind Co Ltd | Hydrophilic filler for gel permeation chromatography |
| JPS5782847A (en) | 1980-11-11 | 1982-05-24 | Canon Inc | Developing powder |
| CA1221196A (en) | 1982-08-17 | 1987-04-28 | Maynard A. Sherwin | Humidity resistant coatings employing branched polymers of t-butyl acrylate |
| JPS59166505A (ja) | 1983-03-10 | 1984-09-19 | Kuraray Co Ltd | 懸濁重合用分散安定剤 |
| US4489192A (en) * | 1983-10-05 | 1984-12-18 | National Starch And Chemical Corporation | Cationic vinyl ester based polymer latices, their preparation and use as formaldehyde-free binders |
| JPS60190223A (ja) * | 1984-03-09 | 1985-09-27 | Kuraray Co Ltd | 乳化重合用分散安定剤 |
| JPH0621125B2 (ja) * | 1984-11-02 | 1994-03-23 | 日本合成化学工業株式会社 | 分散安定剤 |
| JPS61108602A (ja) * | 1984-11-02 | 1986-05-27 | Nippon Synthetic Chem Ind Co Ltd:The | ビニル化合物の懸濁重合用分散安定剤 |
| DE3534858A1 (de) | 1985-09-30 | 1987-04-02 | Basf Lacke & Farben | Loesliches carboxylgruppenhaltiges acrylatcopolymerisat, verfahren zu seiner herstellung und ueberzugsmittel auf der basis des acrylatcopolymerisats |
| JP2565511B2 (ja) | 1987-09-17 | 1996-12-18 | 株式会社クラレ | 塩化ビニルの懸濁重合用分散安定剤 |
| JP2629016B2 (ja) | 1988-03-21 | 1997-07-09 | 株式会社クラレ | ビニル系化合物の懸濁重合用分散安定剤 |
| US5164282A (en) | 1989-04-17 | 1992-11-17 | Xerox Corporation | Processes for the preparation of toners |
| IT1241660B (it) | 1990-03-07 | 1994-01-26 | 3V Ltd | Copolimero vinil acetato/vinil alcool,processo di produzione dello stesso e suo impiego |
| WO1991015518A1 (en) | 1990-04-05 | 1991-10-17 | Kuraray Co., Ltd. | Suspension polymerization of vinylic compound |
| JPH0588251A (ja) | 1991-09-26 | 1993-04-09 | Ricoh Co Ltd | カメラのリモートコントロール装置 |
| TW222282B (enExample) | 1992-03-10 | 1994-04-11 | Kuraray Co | |
| US5484866A (en) | 1993-11-09 | 1996-01-16 | Mobil Oil Corporation | Concentrates of a highly branched polymer and functional fluids prepared therefrom |
| EP0686881A1 (en) | 1994-06-08 | 1995-12-13 | Eastman Kodak Company | Particulate polymer, electrophotographic toner, and preparation method |
| GB2294467B (en) | 1994-10-28 | 1997-03-19 | Sumitomo Chemical Co | Methyl methacrylate polymer |
| US5529719A (en) | 1995-03-27 | 1996-06-25 | Xerox Corporation | Process for preparation of conductive polymeric composite particles |
| JP3474307B2 (ja) | 1995-04-17 | 2003-12-08 | 株式会社クラレ | ビニル系化合物の懸濁重合用分散安定剤 |
| DE19519339A1 (de) | 1995-05-26 | 1996-11-28 | Basf Ag | Wasserlösliche Copolymerisate, die Vernetzer einpolymerisiert enthalten, Verfahren zu ihrer Herstellung und ihre Verwendung |
| JP3385177B2 (ja) | 1997-04-10 | 2003-03-10 | 株式会社日本触媒 | 星形ブロック重合体とその製造方法 |
| EP0872494A3 (en) | 1997-04-17 | 1999-05-12 | Henkel Corporation | Method of preparing inorganic pigment dispersions |
| US6402995B1 (en) * | 1997-07-31 | 2002-06-11 | Seed Co., Ltd. | Process for preparing polyvinyl alcohol contact lenses |
| PT1062248E (pt) | 1998-03-12 | 2004-10-29 | Lucite Int Uk Ltd | Composicao de polimero |
| DE69935259T2 (de) | 1998-06-19 | 2007-10-25 | Kaneka Corp. | Verfahren zur herstellung von verzweigtem polymer |
| SG91279A1 (en) * | 1999-06-09 | 2002-09-17 | Kuraray Co | Polyvinyl alcohol polymer production method and polyvinyl alcohol polymer |
| EP1657261A1 (en) * | 2000-05-29 | 2006-05-17 | Showa Denko K.K. | Porous polymer particle, anion exchanger, producing method thereof, column for ion chromatography, and method for measuring anions |
| US6881761B2 (en) | 2000-05-29 | 2005-04-19 | Showa Denko K.K. | Porous polymer particle, anion exchanger, producing method thereof, column for ion chromatography, and method for measuring anions |
| DE10035119A1 (de) | 2000-07-19 | 2002-01-31 | Basf Ag | Teilverzweigte Polymere |
| JP3995584B2 (ja) * | 2002-12-11 | 2007-10-24 | 株式会社クラレ | ビニル系化合物の懸濁重合用分散安定剤の製造法 |
| EP1433794B1 (en) | 2002-12-11 | 2008-02-20 | Kuraray Co., Ltd. | Dispersion stabilizer for suspension polymerization of vinyl compound and method of producing the same |
| JP2004189889A (ja) | 2002-12-11 | 2004-07-08 | Kuraray Co Ltd | ビニル系化合物の懸濁重合用分散安定剤 |
| RU2265617C2 (ru) * | 2002-12-30 | 2005-12-10 | ФГУП ГНЦ РФ Научно-исследовательский физико-химический институт им. Л.Я. Карпова | Малоразветвленный высокомолекулярный поливинилацетат, способ его получения и поливиниловый спирт на его основе |
| CN1274726C (zh) * | 2003-07-09 | 2006-09-13 | 中国石油化工集团公司 | 一种聚乙烯醇合成方法 |
| US20090076211A1 (en) | 2003-08-18 | 2009-03-19 | Yong Yang | Copolymer surfactants |
| US7402627B2 (en) | 2003-08-18 | 2008-07-22 | Columbia Insurance Company | Precursor colorant composition for latex paint |
| JP4391323B2 (ja) | 2004-06-10 | 2009-12-24 | 日本合成化学工業株式会社 | 懸濁重合用分散剤 |
| DE102004030019A1 (de) | 2004-06-22 | 2006-01-19 | Xetos Ag | Photopolymerisierbare Zusammensetzung |
| EP1832607B1 (en) * | 2004-12-28 | 2015-07-01 | Kaneka Corporation | Crosslinked polymer particle and process for producing the same |
| JP5288683B2 (ja) | 2005-02-02 | 2013-09-11 | 日本合成化学工業株式会社 | ビニル系化合物の懸濁重合用分散安定剤 |
| EP2295471B1 (en) * | 2005-09-16 | 2019-10-23 | Rohm and Haas Company | Method for making swellable particles |
| US20070184732A1 (en) | 2006-02-07 | 2007-08-09 | Lunsford David J | High strength polyvinyl acetate binders |
| ES2423833T3 (es) | 2006-04-12 | 2013-09-24 | Kuraray Co., Ltd. | Estabilizador de dispersión |
| JP2009540032A (ja) | 2006-06-07 | 2009-11-19 | ビーエーエスエフ ソシエタス・ヨーロピア | 酢酸ビニル−スルホナート共重合体の、水への溶解度が低い化合物のための可溶化剤としての使用 |
| CN101506255B (zh) | 2006-08-01 | 2014-02-12 | 日本合成化学工业株式会社 | 乙烯基化合物的悬浮聚合用分散稳定剂 |
| WO2008071662A1 (en) | 2006-12-12 | 2008-06-19 | Unilever Plc | Polymers |
| US20100145001A1 (en) | 2006-12-12 | 2010-06-10 | Unilever Plc | branched organic-inorganic polymers |
| ATE542841T1 (de) | 2006-12-12 | 2012-02-15 | Unilever Nv | Polymere |
| US20100324198A1 (en) | 2007-02-07 | 2010-12-23 | Kuraray Co., Ltd. | Dispersion stabilizer for suspension polymerization of vinyl compound and method of producing vinyl compound polymer |
| DE102007033970A1 (de) | 2007-07-19 | 2009-01-22 | Kuraray Europe Gmbh | Verwendung von getemperten Polyvinylalkoholen als Stabilisatorzusatz von PVC |
| EP2128180A1 (en) | 2008-05-29 | 2009-12-02 | Unilever N.V. | Amphiphilic branched polymers and their use as emulsifiers |
| JP5088251B2 (ja) * | 2008-06-30 | 2012-12-05 | 日本電気株式会社 | 通信システム |
| GB0902052D0 (en) | 2009-02-09 | 2009-03-11 | Unilever Plc | Polymers,composition and use |
| GB0907273D0 (en) | 2009-04-28 | 2009-06-10 | Unilever Plc | Improvements relating to branched polymers |
| FR2945539B1 (fr) | 2009-05-15 | 2012-05-18 | Arkema France | Procede de preparation en suspension d'un pvc greffe sur elastomere. |
| GB0910750D0 (en) | 2009-06-22 | 2009-08-05 | Unilever Plc | Branched polymer dispersants |
| BR112012000909B1 (pt) * | 2009-07-14 | 2018-10-16 | Exxonmobil Chemical Patents Inc | processo para a fabricação de homo e copolímeros de etileno e uso de um c3 a c4 hidrocarboneto ou uma mistura dos mesmos |
| CN102108107A (zh) * | 2011-01-21 | 2011-06-29 | 湖南省湘维有限公司 | 一种低聚合度聚乙烯醇的制备方法 |
| WO2012113896A1 (en) | 2011-02-25 | 2012-08-30 | Basf Se | Process for the preparation of an aqueous polymer latex |
| GB201111609D0 (en) * | 2011-07-06 | 2011-08-24 | Unilever Plc | Copolymers and membranes |
| GB201310652D0 (en) * | 2013-06-14 | 2013-07-31 | Univ Liverpool | Polydendrons |
-
2014
- 2014-03-28 GB GBGB1405624.6A patent/GB201405624D0/en not_active Ceased
-
2015
- 2015-03-27 BR BR112016022117A patent/BR112016022117A2/pt not_active Application Discontinuation
- 2015-03-27 CN CN201811312806.9A patent/CN109354641B/zh active Active
- 2015-03-27 WO PCT/GB2015/050937 patent/WO2015145173A1/en not_active Ceased
- 2015-03-27 EP EP15718376.5A patent/EP3119815B1/en active Active
- 2015-03-27 CN CN201580012806.5A patent/CN106170501B/zh active Active
- 2015-03-27 EP EP18178117.0A patent/EP3434698A1/en not_active Withdrawn
- 2015-03-27 RU RU2016142485A patent/RU2688179C2/ru not_active IP Right Cessation
- 2015-03-27 ES ES15718376.5T patent/ES2684999T3/es active Active
- 2015-03-27 TW TW104109936A patent/TWI748930B/zh active
- 2015-03-27 KR KR1020167029267A patent/KR102356385B1/ko active Active
- 2015-03-27 MX MX2016012327A patent/MX2016012327A/es unknown
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- 2015-03-27 US US15/129,731 patent/US10711073B2/en active Active
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2019
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Also Published As
| Publication number | Publication date |
|---|---|
| CN106170501B (zh) | 2018-11-30 |
| TW201540737A (zh) | 2015-11-01 |
| JP6814851B2 (ja) | 2021-01-20 |
| EP3119815B1 (en) | 2018-06-20 |
| US20170137542A1 (en) | 2017-05-18 |
| MX2016012327A (es) | 2017-04-06 |
| GB201405624D0 (en) | 2014-05-14 |
| RU2016142485A (ru) | 2018-04-28 |
| KR20160140758A (ko) | 2016-12-07 |
| JP2017509782A (ja) | 2017-04-06 |
| CN109354641B (zh) | 2021-05-18 |
| US10711073B2 (en) | 2020-07-14 |
| JP7113617B2 (ja) | 2022-08-05 |
| RU2016142485A3 (enExample) | 2018-09-03 |
| BR112016022117A2 (pt) | 2017-08-15 |
| RU2688179C2 (ru) | 2019-05-21 |
| EP3434698A1 (en) | 2019-01-30 |
| TWI748930B (zh) | 2021-12-11 |
| JP2019196499A (ja) | 2019-11-14 |
| EP3119815A1 (en) | 2017-01-25 |
| CN106170501A (zh) | 2016-11-30 |
| WO2015145173A1 (en) | 2015-10-01 |
| CN109354641A (zh) | 2019-02-19 |
| KR102356385B1 (ko) | 2022-01-26 |
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