CN102108133B - (甲基)丙烯酰基-氮丙啶交联剂和粘合剂聚合物 - Google Patents
(甲基)丙烯酰基-氮丙啶交联剂和粘合剂聚合物 Download PDFInfo
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- CN102108133B CN102108133B CN200910261937.3A CN200910261937A CN102108133B CN 102108133 B CN102108133 B CN 102108133B CN 200910261937 A CN200910261937 A CN 200910261937A CN 102108133 B CN102108133 B CN 102108133B
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- methyl
- monomer
- acrylate
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- 239000003431 cross linking reagent Substances 0.000 title abstract 3
- 239000002998 adhesive polymer Substances 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract description 86
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 238000004132 cross linking Methods 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims description 137
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 46
- 239000002253 acid Substances 0.000 claims description 35
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- 239000000126 substance Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
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- RCLLINSDAJVOHP-UHFFFAOYSA-N n-ethyl-n',n'-dimethylprop-2-enehydrazide Chemical compound CCN(N(C)C)C(=O)C=C RCLLINSDAJVOHP-UHFFFAOYSA-N 0.000 claims description 3
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 claims description 3
- SCMVPOVMOHQFKU-UHFFFAOYSA-N 1-(aziridin-1-yl)prop-2-en-1-one Chemical compound C=CC(=O)N1CC1 SCMVPOVMOHQFKU-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
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- 238000004458 analytical method Methods 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
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- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
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- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
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- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical group C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 3
- 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
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- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 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
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005418 vegetable material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
-
- 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
-
- 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
-
- 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
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- 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
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesive Tapes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910261937.3A CN102108133B (zh) | 2009-12-23 | 2009-12-23 | (甲基)丙烯酰基-氮丙啶交联剂和粘合剂聚合物 |
| US12/849,878 US8263711B2 (en) | 2009-12-23 | 2010-08-04 | (Meth)acryloyl-aziridine crosslinking agents and adhesive polymers |
| PCT/US2010/060219 WO2011087664A1 (en) | 2009-12-23 | 2010-12-14 | (meth)acryloyl-aziridine crosslinking agents and adhesive polymers |
| EP10795179.0A EP2516391B1 (en) | 2009-12-23 | 2010-12-14 | (Meth)acryloyl-aziridine crosslinking agents and adhesive polymers |
| JP2012546026A JP2013515819A (ja) | 2009-12-23 | 2010-12-14 | （メタ）アクリロイル−アジリジン架橋剤及び接着剤ポリマー |
| KR1020127018975A KR20120112607A (ko) | 2009-12-23 | 2010-12-14 | (메트)아크릴로일-아지리딘 가교결합제 및 접착성 중합체 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910261937.3A CN102108133B (zh) | 2009-12-23 | 2009-12-23 | (甲基)丙烯酰基-氮丙啶交联剂和粘合剂聚合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102108133A CN102108133A (zh) | 2011-06-29 |
| CN102108133B true CN102108133B (zh) | 2014-12-10 |
Family
ID=44151985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200910261937.3A Expired - Fee Related CN102108133B (zh) | 2009-12-23 | 2009-12-23 | (甲基)丙烯酰基-氮丙啶交联剂和粘合剂聚合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8263711B2 (enExample) |
| EP (1) | EP2516391B1 (enExample) |
| JP (1) | JP2013515819A (enExample) |
| KR (1) | KR20120112607A (enExample) |
| CN (1) | CN102108133B (enExample) |
| WO (1) | WO2011087664A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8067504B2 (en) * | 2009-08-25 | 2011-11-29 | 3M Innovative Properties Company | Acrylic pressure-sensitive adhesives with acylaziridine crosslinking agents |
| US10029816B2 (en) | 2010-05-26 | 2018-07-24 | Avery Dennison Retail Information Services, Llc | Pressure sensitive labels for use in a cold transfer method and process for making |
| CN103282429B (zh) | 2010-12-29 | 2015-11-25 | 3M创新有限公司 | 具有三嗪-环氧交联体系的压敏粘合剂 |
| WO2014070230A1 (en) | 2012-10-31 | 2014-05-08 | Avery Dennison Corporation | Wash durable cold apply adhesive for apparel labeling and embellishment |
| BR112015014099A2 (pt) * | 2012-12-14 | 2017-07-11 | 3M Innovative Properties Co | método de fabricação de composições viscoelásticas embaladas pela polimerização de materiais etilenicamente insaturados com o uso de radiação ionizante |
| WO2014116461A1 (en) | 2013-01-24 | 2014-07-31 | 3M Innovative Properties Company | Photoinitiated oligomerization of methacrylate esters |
| KR20150143610A (ko) | 2013-04-15 | 2015-12-23 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | (메트)아크릴레이트 기 및 올레핀 기를 갖는 가교결합제를 포함하는 접착제 및 방법 |
| EP2886620B1 (en) | 2013-12-18 | 2019-11-27 | 3M Innovative Properties Company | Post-curable pressure-sensitive adhesive |
| JP6369023B2 (ja) * | 2014-01-08 | 2018-08-08 | 東洋インキＳｃホールディングス株式会社 | 反応性モノマーおよびそれを用いてなる樹脂組成物 |
| KR20160138097A (ko) | 2014-03-26 | 2016-12-02 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 자외선 경화된 (메트)아크릴레이트 감압 접착제 조성물 및 이의 제조 방법 |
| CN104449426B (zh) * | 2014-11-20 | 2016-07-06 | 北京天山新材料技术有限公司 | 一种可紫外光固化耐高温压敏胶 |
| CN104559827B (zh) * | 2014-12-29 | 2017-11-21 | 3M创新有限公司 | 可压缩的微米级聚合物颗粒及其用途、可固化组合物及其制备方法、压敏粘合剂、胶带 |
| US10920116B2 (en) * | 2015-04-13 | 2021-02-16 | 3M Innovative Properties Company | Method of preparing crosslinked pressure-sensitive adhesives using a light-emitting diode for crosslinking |
| EP3310867B1 (en) * | 2015-06-22 | 2021-04-21 | 3M Innovative Properties Company | Pressure sensitive adhesive comprising (meth)acrylic polymer and amino acid crosslinker |
| KR102126094B1 (ko) * | 2015-11-19 | 2020-06-23 | 주식회사 엘지화학 | 라디칼 경화형 접착제 조성물 및 이를 포함하는 편광판 |
| CN106928865B (zh) | 2015-12-31 | 2021-01-12 | 3M创新有限公司 | 可固化的粘合剂组合物、压敏粘合剂和制备压敏粘合剂的方法 |
| WO2020020714A1 (en) | 2018-07-23 | 2020-01-30 | Dsm Ip Assets B.V. | Multi-aziridine compound |
| CN116018362A (zh) * | 2020-09-30 | 2023-04-25 | 富士胶片和光纯药株式会社 | 二次电池用粘合剂组合物、电极用组合物、电极片及二次电池以及这些电极片及二次电池的制造方法 |
| KR102495336B1 (ko) * | 2021-11-26 | 2023-02-06 | 울산과학기술원 | 아지리딘기를 함유하는 고분자 브러시를 포함하는 가교제, 이의 제조방법 및 이의 용도 |
| WO2024160696A2 (en) * | 2023-01-31 | 2024-08-08 | Basf Se | Curable composition, 3d-printed object formed therefrom and process of forming the same |
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| US7393901B1 (en) * | 2007-02-16 | 2008-07-01 | 3M Innovative Properties Company | Acrylate adhesives containing silica nanoparticles crosslinked with polyfunctional aziridines |
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| US6734256B1 (en) * | 1998-12-29 | 2004-05-11 | 3M Innovative Properties Company | Block copolymer hot-melt processable adhesives, methods of their preparation, and articles therefrom |
| ITMI991539A1 (it) * | 1999-07-13 | 2001-01-13 | Alcantara Spa | Additivo utile per rendere ignifughi materiali tessili in particolaretessuti non tessuti microfribrosi sintetici procedimento per la sua pr |
| US6448337B1 (en) | 1999-10-07 | 2002-09-10 | 3M Innovative Properties Company | Pressure sensitive adhesives possessing high load bearing capability |
| EP1179577A1 (en) | 2000-08-07 | 2002-02-13 | 3M Innovative Properties Company | A laser-cuttable multi-layer sheet material |
| MXPA05002933A (es) | 2002-09-26 | 2005-09-30 | Ucb Sa | Adhesivos sensibles a la presion resistentes a blanquecimiento con agua, removibles. |
| US20050070688A1 (en) * | 2003-09-26 | 2005-03-31 | 3M Innovative Properties Company | Reactive hydrophilic oligomers |
| US7074839B2 (en) | 2004-03-01 | 2006-07-11 | 3M Innovative Properties Company | Crosslinkable hydrophilic materials from reactive oligomers having pendent photoinitiator groups |
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| US7385020B2 (en) | 2006-10-13 | 2008-06-10 | 3M Innovative Properties Company | 2-octyl (meth)acrylate adhesive composition |
| KR100867948B1 (ko) * | 2006-12-13 | 2008-11-11 | 제일모직주식회사 | 유기 절연막 형성용 감광성 수지 조성물 및 이를 포함하는소자 |
| US20080200587A1 (en) | 2007-02-16 | 2008-08-21 | 3M Innovative Properties Company | Pressure-sensitive adhesive containing acicular silica particles crosslinked with polyfunctional aziridines |
| US7652095B2 (en) * | 2007-06-20 | 2010-01-26 | 3M Innovative Properties Company | Pressure-sensitive adhesive containing aziridinyl silanes |
| EP2178930B1 (en) * | 2007-06-29 | 2012-10-24 | 3M Innovative Properties Company | A functional polymer with a pendant color changing indicator |
| US7652103B2 (en) * | 2008-02-14 | 2010-01-26 | 3M Innovative Properties Company | Acrylic pressure-sensitive adhesives with aziridine crosslinking agents |
| US7714076B2 (en) | 2008-03-27 | 2010-05-11 | 3M Innovative Properties Company | Acrylic pressure-sensitive adhesives with aziridine crosslinking agents |
| US7838110B2 (en) * | 2008-12-02 | 2010-11-23 | 3M Innovative Properties Company | Aziridine-functional photoactive crosslinking compounds |
-
2009
- 2009-12-23 CN CN200910261937.3A patent/CN102108133B/zh not_active Expired - Fee Related
-
2010
- 2010-08-04 US US12/849,878 patent/US8263711B2/en not_active Expired - Fee Related
- 2010-12-14 EP EP10795179.0A patent/EP2516391B1/en not_active Not-in-force
- 2010-12-14 WO PCT/US2010/060219 patent/WO2011087664A1/en not_active Ceased
- 2010-12-14 KR KR1020127018975A patent/KR20120112607A/ko not_active Withdrawn
- 2010-12-14 JP JP2012546026A patent/JP2013515819A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7393901B1 (en) * | 2007-02-16 | 2008-07-01 | 3M Innovative Properties Company | Acrylate adhesives containing silica nanoparticles crosslinked with polyfunctional aziridines |
Non-Patent Citations (1)
| Title |
|---|
| JP昭58-26869A 1983.02.17 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US20110152445A1 (en) | 2011-06-23 |
| EP2516391A1 (en) | 2012-10-31 |
| KR20120112607A (ko) | 2012-10-11 |
| US8263711B2 (en) | 2012-09-11 |
| JP2013515819A (ja) | 2013-05-09 |
| WO2011087664A1 (en) | 2011-07-21 |
| EP2516391B1 (en) | 2015-03-11 |
| CN102108133A (zh) | 2011-06-29 |
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