ES2543044T3 - Copolímeros de alcohol polivinílico/acrilato de alquilo solubles en agua fría y películas de los mismos - Google Patents
Copolímeros de alcohol polivinílico/acrilato de alquilo solubles en agua fría y películas de los mismos Download PDFInfo
- Publication number
- ES2543044T3 ES2543044T3 ES11808485.4T ES11808485T ES2543044T3 ES 2543044 T3 ES2543044 T3 ES 2543044T3 ES 11808485 T ES11808485 T ES 11808485T ES 2543044 T3 ES2543044 T3 ES 2543044T3
- Authority
- ES
- Spain
- Prior art keywords
- copolymer
- cold water
- mav
- alkyl acrylate
- voh
- 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.)
- Active
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 239000004372 Polyvinyl alcohol Substances 0.000 title description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 title description 5
- 229920000800 acrylic rubber Polymers 0.000 title description 2
- 229920001577 copolymer Polymers 0.000 claims abstract description 93
- 239000000203 mixture Substances 0.000 claims abstract description 29
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract description 18
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 17
- 238000004090 dissolution Methods 0.000 claims abstract description 17
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000010828 elution Methods 0.000 claims abstract description 6
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 38
- 239000007787 solid Substances 0.000 claims description 23
- 238000005538 encapsulation Methods 0.000 claims description 13
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- 229920005604 random copolymer Polymers 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 71
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 238000000034 method Methods 0.000 description 37
- 229920000642 polymer Polymers 0.000 description 36
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 30
- 239000000178 monomer Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 238000007127 saponification reaction Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920002689 polyvinyl acetate Polymers 0.000 description 7
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 239000003505 polymerization initiator Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 238000007922 dissolution test Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920006280 packaging film Polymers 0.000 description 4
- 239000012785 packaging film Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- -1 for example Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- UUPWEGAONCOIFJ-UHFFFAOYSA-N CCCCC(CC)COC(=O)OOC(O)=O Chemical compound CCCCC(CC)COC(=O)OOC(O)=O UUPWEGAONCOIFJ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IKBVWGOHCLVYTA-UHFFFAOYSA-N butan-2-yl butan-2-yloxy carbonate Chemical compound CCC(C)OOC(=O)OC(C)CC IKBVWGOHCLVYTA-UHFFFAOYSA-N 0.000 description 1
- ZGPBOPXFOJBLIV-UHFFFAOYSA-N butoxycarbonyloxy butyl carbonate Chemical compound CCCCOC(=O)OOC(=O)OCCCC ZGPBOPXFOJBLIV-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
- 238000000105 evaporative light scattering detection Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- QWVBGCWRHHXMRM-UHFFFAOYSA-N hexadecoxycarbonyloxy hexadecyl carbonate Chemical compound CCCCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCCCC QWVBGCWRHHXMRM-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 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
-
- 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
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
- Y10T428/2998—Coated including synthetic resin or polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201061459979P | 2010-12-22 | 2010-12-22 | |
| US201061459979P | 2010-12-22 | ||
| PCT/US2011/065473 WO2012087821A1 (en) | 2010-12-22 | 2011-12-16 | Cold water soluble polyvinyl alcohol/alkyl acrylate copolymers and films thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2543044T3 true ES2543044T3 (es) | 2015-08-14 |
Family
ID=45478541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11808485.4T Active ES2543044T3 (es) | 2010-12-22 | 2011-12-16 | Copolímeros de alcohol polivinílico/acrilato de alquilo solubles en agua fría y películas de los mismos |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10316124B2 (enExample) |
| EP (1) | EP2655447B1 (enExample) |
| JP (3) | JP5931088B2 (enExample) |
| CN (1) | CN103403043A (enExample) |
| ES (1) | ES2543044T3 (enExample) |
| WO (1) | WO2012087821A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105143425B (zh) * | 2013-03-15 | 2019-04-09 | 蒙诺苏尔有限公司 | 用于延迟释放的水溶性膜 |
| US10808210B2 (en) | 2013-03-15 | 2020-10-20 | Monosol, Llc | Water-soluble film for delayed release |
| CN111679417B (zh) | 2013-12-06 | 2022-08-19 | 3M创新有限公司 | 具有保护元件的半潜式显微镜物镜和物镜在多光子成像方法中的用途 |
| HUE048811T2 (hu) * | 2013-12-25 | 2020-08-28 | Kuraray Co | Módosított polivinilalkohol és az azt tartalmazó vízoldható film |
| US10898821B2 (en) * | 2015-06-02 | 2021-01-26 | Moose Creative Management Pty Limited | Adhesive toy beads |
| WO2017035741A1 (en) * | 2015-08-31 | 2017-03-09 | Wacker Chemie Ag | Additive pack |
| CN108779274B (zh) | 2016-04-13 | 2022-08-09 | 蒙诺苏尔有限公司 | 水溶性膜、采用所述膜的包以及其制造和使用方法 |
| CA3023508A1 (en) | 2016-06-13 | 2017-12-21 | The Procter & Gamble Company | Water-soluble unit dose articles made from a combination of different films and containing household care compositions |
| JP7204488B2 (ja) | 2016-06-13 | 2023-01-16 | モノソル リミテッド ライアビリティ カンパニー | 水溶性パケット |
| US10443024B2 (en) * | 2016-06-13 | 2019-10-15 | Monosol, Llc | Water-soluble unit dose articles made from a combination of different films |
| JP7059205B2 (ja) | 2016-06-13 | 2022-04-25 | モノソル リミテッド ライアビリティ カンパニー | 水溶性の密封強度を改善するための第１のフィルムおよび第２のフィルムの使用 |
| US10745655B2 (en) | 2016-06-13 | 2020-08-18 | The Procter & Gamble Company | Water-soluble unit dose articles made from a combination of different films and containing household care compositions |
| WO2017218443A1 (en) | 2016-06-13 | 2017-12-21 | The Procter & Gamble Company | Water-soluble unit dose articles made from a combination of different films and containing household care compositions |
| US10858457B2 (en) | 2017-08-17 | 2020-12-08 | Kuraray Co., Ltd. | Particulate polyvinyl alcohol copolymers, process for making and uses of the same |
| EP3699206B1 (en) | 2017-10-18 | 2025-08-06 | Mitsubishi Chemical Corporation | Chemical agent package and use of a water-soluble film |
| TWI704868B (zh) * | 2018-03-08 | 2020-09-21 | 日商可樂麗股份有限公司 | 農藥用展著劑及農藥散布液 |
| US12221552B2 (en) | 2019-02-06 | 2025-02-11 | Monosol, Llc | Water-soluble coatings for substrate surfaces |
| CN110713749B (zh) * | 2019-10-16 | 2022-07-29 | 东南大学 | 一种电响应聚合物材料及其制备方法与应用 |
| US12311282B2 (en) | 2022-01-01 | 2025-05-27 | Spin Master Ltd. | Kit with plurality of blocks for constructing craft |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1720806C2 (de) | 1968-03-19 | 1982-09-23 | Hoechst Ag, 6000 Frankfurt | Verfahren zur kontinuierlichen Polymerisation von Vinylestern |
| US3692754A (en) * | 1969-04-05 | 1972-09-19 | Masaaki Hirooka | Highly lactonized copolymers and alternating copolymers using unsaturated ethers |
| US3689469A (en) | 1969-07-15 | 1972-09-05 | Du Pont | Copolymers of vinyl alcohol and methyl methacrylate and uses therefor |
| JPS4936797A (enExample) | 1972-08-11 | 1974-04-05 | ||
| US4048413A (en) | 1975-12-08 | 1977-09-13 | Scm Corporation | High-conversion drift-free batch-type addition copolymerization |
| US4156047A (en) | 1976-08-18 | 1979-05-22 | E. I. Du Pont De Nemours And Company | Water-soluble films from polyvinyl alcohol compositions |
| DE3312668A1 (de) * | 1983-04-08 | 1984-10-11 | Basf Ag, 6700 Ludwigshafen | Wasserloesliche polymere mit geringer hygroskopie |
| US4618648A (en) | 1985-04-26 | 1986-10-21 | Air Products And Chemicals, Inc. | Copolymers of vinyl alcohol and poly(alkyleneoxy)acrylates |
| JPH0627205B2 (ja) * | 1986-12-27 | 1994-04-13 | 日本合成化学工業株式会社 | アルカリ性物質包装用のポリビニルアルコ−ルフイルム |
| US4772663A (en) | 1987-01-16 | 1988-09-20 | Air Products And Chemicals, Inc. | Copolymers of vinyl alcohol and acrylates |
| JPS63182313A (ja) | 1987-01-16 | 1988-07-27 | エアー．プロダクツ．アンド．ケミカルス．インコーポレーテッド | 酢酸ビニル−アクリレート系共重合体 |
| US4948857A (en) | 1987-01-16 | 1990-08-14 | Air Products And Chemicals, Inc. | Copolymers of vinyl acetate and acrylates |
| US4990335A (en) | 1987-03-25 | 1991-02-05 | E. I. Du Pont De Nemours And Company | Use of vinyl alcohol homopolymer and copolymers for tableting active materials |
| US4747976A (en) | 1987-05-14 | 1988-05-31 | The Clorox Company | PVA films with nonhydrolyzable anionic comonomers for packaging detergents |
| US4885105A (en) * | 1987-05-14 | 1989-12-05 | The Clorox Company | Films from PVA modified with nonhydrolyzable anionic comonomers |
| US5436293A (en) | 1994-02-28 | 1995-07-25 | E. I. Du Pont De Nemours And Company | Poly(vinyl alcohol) polymer blend textile sizes with improved ability to be desized |
| US5362515A (en) | 1994-02-28 | 1994-11-08 | E. I. Du Pont De Nemours And Company | Poly(vinyl alcohol)copolymer sizes having high capacity to be desized |
| JPH0936797A (ja) | 1995-07-17 | 1997-02-07 | Kokusai Electric Co Ltd | 光通信機能付無線呼出受信機 |
| WO1997019961A1 (en) * | 1995-11-29 | 1997-06-05 | E.I. Du Pont De Nemours And Company | Polyvinyl acetal copolymers and their preparation |
| US6387991B1 (en) | 1995-12-18 | 2002-05-14 | E. I. Du Pont De Nemours & Company | Poly(vinyl alcohol) copolymer ionomers, their preparation and use in textile sizes |
| US6946501B2 (en) | 2001-01-31 | 2005-09-20 | The Procter & Gamble Company | Rapidly dissolvable polymer films and articles made therefrom |
| US7799752B2 (en) * | 2002-08-14 | 2010-09-21 | Quest International Services B.V. | Compositions comprising encapsulated material |
| JP4056859B2 (ja) | 2002-11-11 | 2008-03-05 | 日本合成化学工業株式会社 | 水溶性フィルム |
| US6821590B2 (en) * | 2003-02-14 | 2004-11-23 | Monosol, Llc | Starch-loaded polyvinyl alcohol copolymer film |
| US7022656B2 (en) * | 2003-03-19 | 2006-04-04 | Monosol, Llc. | Water-soluble copolymer film packet |
| US6818709B1 (en) | 2003-07-11 | 2004-11-16 | Celanese International Corporation | Production of vinyl alcohol copolymers |
| US7786229B2 (en) | 2003-07-11 | 2010-08-31 | Sekisui Specialty Chemicals America, Llc | Vinyl alcohol copolymers for use in aqueous dispersions and melt extruded articles |
| JP2005089655A (ja) * | 2003-09-18 | 2005-04-07 | Japan Vam & Poval Co Ltd | ポリビニルアルコール系樹脂およびフィルム |
| JP2005139240A (ja) * | 2003-11-04 | 2005-06-02 | Japan Vam & Poval Co Ltd | 水溶性フィルムおよび個別包装材 |
| US7767282B2 (en) * | 2004-08-10 | 2010-08-03 | E.I. Du Pont De Nemours And Company | Copolymers of vinyl alcohol and itaconic acid and uses thereof |
| US8790632B2 (en) | 2004-10-07 | 2014-07-29 | Actamax Surgical Materials, Llc | Polymer-based tissue-adhesive form medical use |
| US7714086B2 (en) * | 2005-02-23 | 2010-05-11 | The Procter & Gamble Company | Polyvinyl alcohol co-polymer, and water-soluble films and pouches formed therefrom |
| US7622132B2 (en) | 2005-06-27 | 2009-11-24 | Elc Management, Llc | Encapsulated cosmetic composition |
| US7476325B2 (en) * | 2005-08-09 | 2009-01-13 | E.I. Du Pont De Nemours And Company | Treatment of recreational water |
| BRPI0604797A (pt) * | 2005-11-30 | 2007-10-09 | Goodyear Tire & Rubber | polìmeros de borracha funcionalizados |
| US7745517B2 (en) | 2006-05-02 | 2010-06-29 | Sekisui Specialty Chemicals America, Llc | Polyvinyl alcohol films with improved resistance to oxidizing chemicals |
| US7781506B2 (en) * | 2007-01-26 | 2010-08-24 | E.I. Du Pont De Nemours And Company | Poly(vinyl alcohol) composition comprising a polyol |
| JP4835719B2 (ja) | 2008-05-22 | 2011-12-14 | ソニー株式会社 | 固体撮像装置及び電子機器 |
-
2011
- 2011-12-16 CN CN2011800680936A patent/CN103403043A/zh active Pending
- 2011-12-16 ES ES11808485.4T patent/ES2543044T3/es active Active
- 2011-12-16 EP EP11808485.4A patent/EP2655447B1/en not_active Revoked
- 2011-12-16 WO PCT/US2011/065473 patent/WO2012087821A1/en not_active Ceased
- 2011-12-16 US US13/328,338 patent/US10316124B2/en active Active
- 2011-12-16 JP JP2013546257A patent/JP5931088B2/ja active Active
-
2015
- 2015-11-04 JP JP2015216584A patent/JP6117893B2/ja active Active
-
2017
- 2017-03-22 JP JP2017055585A patent/JP6454745B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP5931088B2 (ja) | 2016-06-08 |
| JP2017141461A (ja) | 2017-08-17 |
| CN103403043A (zh) | 2013-11-20 |
| EP2655447B1 (en) | 2015-06-10 |
| US20120164424A1 (en) | 2012-06-28 |
| US10316124B2 (en) | 2019-06-11 |
| JP6454745B2 (ja) | 2019-01-16 |
| JP6117893B2 (ja) | 2017-04-19 |
| JP2016065244A (ja) | 2016-04-28 |
| JP2014503656A (ja) | 2014-02-13 |
| EP2655447A1 (en) | 2013-10-30 |
| WO2012087821A1 (en) | 2012-06-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2543044T3 (es) | Copolímeros de alcohol polivinílico/acrilato de alquilo solubles en agua fría y películas de los mismos | |
| US7932328B2 (en) | Vinyl alcohol copolymers for use in aqueous dispersions and melt extruded articles | |
| JP5306349B2 (ja) | 連続的重合法 | |
| Ma et al. | Synthesis and biological response of casein-based silica nano-composite film for drug delivery system | |
| CN101885905A (zh) | 聚合物/无机纳米粒子复合纳米颗粒及其制备和用途 | |
| MX2011013031A (es) | Metodo para producir composiciones polimericas espumables, metodo para producir composiciones polimericas espumadas a partir de las mismas, composiciones polimericas espumadas y cintas adhesiva obtenida a partir de estas. | |
| IL239038A (en) | Micro-particles of active substances | |
| ES2763078T3 (es) | Composición polimérica polimodal | |
| Lou et al. | Fabrication and aggregation of thermoresponsive glucose-functionalized double hydrophilic copolymers | |
| Lehmann | Acrylic latices from redispersable powders for peroral and transdermal drug formulations | |
| CN106536600B (zh) | 用于泡罩包装的具有热封性的聚合物乳液及其制备方法 | |
| Nopwinyuwong et al. | Effects of nanoparticle concentration and plasticizer type on colorimetric behavior of polydiacetylene/silica nanocomposite as time-temperature indicator | |
| CN108485399A (zh) | 一种涂布用pvdc水性乳液 | |
| US5492940A (en) | Acrylic/lactam resin compositions and method of producing same | |
| Willis Jr et al. | Polymer–drug interacted systems in the physicochemical design of pharmaceutical dosage forms I: drug salts with PVM/MA and with a PVM/MA hemi-ester | |
| HK1190741A (en) | Cold water soluble polyvinyl alcohol/alkyl acrylate copolymers and films thereof | |
| CA2617080A1 (en) | Copolymers based on n-vinylpyrrolidone and branched aliphatic carboxylic acids, and their use as solubilizers | |
| Atayde Jr et al. | Temperature-and pH-dependent drug release of block copolymers of methacrylic acid and poly (ethylene glycol) methyl ether methacrylates | |
| CN114196055A (zh) | 一种高氧气阻隔涂布膜及其制备方法 | |
| KR20150087394A (ko) | 잔류 단량체 함량이 낮은 폴리비닐에스테르 조성물을 생산하는 방법 | |
| ES2656683T3 (es) | Copolímeros de ésteres vinílicos de ácidos grasos con propiedades de cera | |
| ES2215477B1 (es) | Procedimiento para preparar dispersiones polimericas acuosas de altas prestaciones. | |
| CN104258405A (zh) | 一种用于包衣的聚丙烯酸树脂 | |
| ISA | Synthesis and characterisation of pentacosa-10, 12-diynoic Acid–poly (styrene-butyl acrylate) latex for gamma radiation indicator | |
| CN106008788A (zh) | 一种低渗透性缓释包衣材料及其制备方法 |