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 PDF

Info

Publication number: ES2543044T3
Authority: ES; Spain
Prior art keywords: copolymer; cold water; mav; alkyl acrylate; voh
Prior art date: 2010-12-22
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

Application number

ES11808485.4T

Other languages

English (en)

Spanish (es)

Inventor

Richard Vicari

Bret Hann

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sekisui Specialty Chemicals America LLC

Original Assignee

Sekisui Specialty Chemicals America LLC

Priority date (The priority date 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 date listed.)

2010-12-22

Filing date

2011-12-16

Publication date

2015-08-14

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=45478541&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ES2543044(T3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2011-12-16 Application filed by Sekisui Specialty Chemicals America LLC filed Critical Sekisui Specialty Chemicals America LLC

2015-08-14 Application granted granted Critical

2015-08-14 Publication of ES2543044T3 publication Critical patent/ES2543044T3/es

Status Active legal-status Critical Current

2031-12-16 Anticipated expiration legal-status Critical

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)

ES11808485.4T 2010-12-22 2011-12-16 Copolímeros de alcohol polivinílico/acrilato de alquilo solubles en agua fría y películas de los mismos Active ES2543044T3 (es)

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 (2)
EP (1)	EP2655447B1 (2)
JP (3)	JP5931088B2 (2)
CN (1)	CN103403043A (2)
ES (1)	ES2543044T3 (2)
WO (1)	WO2012087821A1 (2)

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ES2775194T3 (es)	2013-12-25	2020-07-24	Kuraray Co	Alcohol polivinílico modificado y película soluble en agua que contiene el mismo
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2011
- 2011-12-16 JP JP2013546257A patent/JP5931088B2/ja active Active
- 2011-12-16 US US13/328,338 patent/US10316124B2/en 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 ES ES11808485.4T patent/ES2543044T3/es active Active
- 2011-12-16 CN CN2011800680936A patent/CN103403043A/zh active Pending
2015
- 2015-11-04 JP JP2015216584A patent/JP6117893B2/ja active Active
2017
- 2017-03-22 JP JP2017055585A patent/JP6454745B2/ja active Active

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Publication number	Publication date
JP6117893B2 (ja)	2017-04-19
EP2655447A1 (en)	2013-10-30
JP2014503656A (ja)	2014-02-13
JP5931088B2 (ja)	2016-06-08
JP2016065244A (ja)	2016-04-28
WO2012087821A1 (en)	2012-06-28
US10316124B2 (en)	2019-06-11
US20120164424A1 (en)	2012-06-28
CN103403043A (zh)	2013-11-20
JP2017141461A (ja)	2017-08-17
EP2655447B1 (en)	2015-06-10
JP6454745B2 (ja)	2019-01-16

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