JP2018504509A5 - - Google Patents
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- Publication number
- JP2018504509A5 JP2018504509A5 JP2017550098A JP2017550098A JP2018504509A5 JP 2018504509 A5 JP2018504509 A5 JP 2018504509A5 JP 2017550098 A JP2017550098 A JP 2017550098A JP 2017550098 A JP2017550098 A JP 2017550098A JP 2018504509 A5 JP2018504509 A5 JP 2018504509A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- reaction mixture
- acrylic acid
- acid ester
- substituted
- 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.)
- Granted
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- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 36
- 238000000034 method Methods 0.000 claims 31
- 239000011541 reaction mixture Substances 0.000 claims 20
- 239000000203 mixture Substances 0.000 claims 15
- 239000000178 monomer Substances 0.000 claims 15
- 229920000642 polymer Polymers 0.000 claims 14
- 239000002904 solvent Substances 0.000 claims 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 12
- 229920002554 vinyl polymer Polymers 0.000 claims 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 238000010526 radical polymerization reaction Methods 0.000 claims 7
- 230000027756 respiratory electron transport chain Effects 0.000 claims 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 6
- 239000003999 initiator Substances 0.000 claims 6
- 239000012074 organic phase Substances 0.000 claims 6
- 229920001400 block copolymer Polymers 0.000 claims 5
- 239000003446 ligand Substances 0.000 claims 5
- 230000000379 polymerizing effect Effects 0.000 claims 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- IPXBCGPHSSHWPS-UHFFFAOYSA-N NN.[Cu] Chemical compound NN.[Cu] IPXBCGPHSSHWPS-UHFFFAOYSA-N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- RYWGNBFHIFRNEP-UHFFFAOYSA-N (4-benzoylphenyl) 2-methylprop-2-enoate Chemical group C1=CC(OC(=O)C(=C)C)=CC=C1C(=O)C1=CC=CC=C1 RYWGNBFHIFRNEP-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 claims 3
- 150000004056 anthraquinones Chemical class 0.000 claims 3
- 239000012965 benzophenone Substances 0.000 claims 3
- 150000008366 benzophenones Chemical class 0.000 claims 3
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 239000012267 brine Substances 0.000 claims 3
- 238000001035 drying Methods 0.000 claims 3
- 238000001704 evaporation Methods 0.000 claims 3
- 230000008020 evaporation Effects 0.000 claims 3
- 239000000706 filtrate Substances 0.000 claims 3
- 238000001914 filtration Methods 0.000 claims 3
- 239000011148 porous material Substances 0.000 claims 3
- 239000000843 powder Substances 0.000 claims 3
- 239000000047 product Substances 0.000 claims 3
- 239000011780 sodium chloride Substances 0.000 claims 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims 3
- 238000005406 washing Methods 0.000 claims 3
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone powder Natural products C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims 3
- 150000007964 xanthones Chemical class 0.000 claims 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 claims 2
- 238000004132 cross linking Methods 0.000 claims 2
- AWWJYEJSCIDADZ-UHFFFAOYSA-N dimethyl 2,6-dibromoheptanedioate Chemical compound COC(=O)C(Br)CCCC(Br)C(=O)OC AWWJYEJSCIDADZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 230000009477 glass transition Effects 0.000 claims 2
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 claims 2
- 125000001792 phenanthrenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 2
- 238000010926 purge Methods 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- 150000004053 quinones Chemical class 0.000 claims 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims 2
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical class NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 claims 2
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 238000013019 agitation Methods 0.000 claims 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- SCOAVUHOIJMIBW-UHFFFAOYSA-N phenanthrene-1,2-dione Chemical class C1=CC=C2C(C=CC(C3=O)=O)=C3C=CC2=C1 SCOAVUHOIJMIBW-UHFFFAOYSA-N 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/570,060 US9587062B2 (en) | 2014-12-15 | 2014-12-15 | Photocrosslinkable block copolymers for hot-melt adhesives |
| US14/570,060 | 2014-12-15 | ||
| PCT/US2015/065660 WO2016100251A1 (en) | 2014-12-15 | 2015-12-15 | Photocrosslinkable block copolymers for hot-melt adhesives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018504509A JP2018504509A (ja) | 2018-02-15 |
| JP2018504509A5 true JP2018504509A5 (https=) | 2019-01-31 |
| JP6689875B2 JP6689875B2 (ja) | 2020-04-28 |
Family
ID=56110517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017550098A Active JP6689875B2 (ja) | 2014-12-15 | 2015-12-15 | ホットメルト接着剤用の光架橋性ブロックコポリマー |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9587062B2 (https=) |
| EP (1) | EP3233940B1 (https=) |
| JP (1) | JP6689875B2 (https=) |
| CN (1) | CN107207653B (https=) |
| BR (1) | BR112017012639A2 (https=) |
| WO (1) | WO2016100251A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10414953B2 (en) | 2016-02-19 | 2019-09-17 | Avery Dennison Corporation | Two stage methods for processing adhesives and related compositions |
| FR3047991B1 (fr) * | 2016-02-24 | 2020-03-20 | Arkema France | Composition polymerisable de faible viscosite precurseur de materiaux renforces a l'impact |
| CN110099939B (zh) * | 2016-10-25 | 2022-09-06 | 艾利丹尼森公司 | 在主链中具有光引发剂基团的嵌段聚合物及其用于粘合剂组合物中的用途 |
| AU2018392478B2 (en) | 2017-12-19 | 2023-03-16 | Avery Dennison Corporation | Post-polymerization functionalization of pendant functional groups |
| KR102203870B1 (ko) | 2018-04-12 | 2021-01-18 | 주식회사 엘지화학 | 임시고정용 점착시트 및 이를 사용한 반도체 장치의 제조 방법 |
| KR20240037375A (ko) * | 2018-11-08 | 2024-03-21 | 미쯔비시 케미컬 주식회사 | 점착제 수지 조성물, 점착 시트, 활성 에너지선 경화성 점착 시트, 광학 부재, 화상 표시 장치용 적층체 및 화상 표시 장치 |
| JPWO2020149387A1 (ja) * | 2019-01-16 | 2021-02-18 | 積水フーラー株式会社 | 架橋性ブロック共重合体及びその製造方法並びに伸縮性部材 |
| WO2020149385A1 (ja) * | 2019-01-16 | 2020-07-23 | 積水フーラー株式会社 | 架橋性ブロック共重合体及びコーティング剤 |
| JP7289148B2 (ja) * | 2019-01-16 | 2023-06-09 | 積水フーラー株式会社 | 架橋性ブロック共重合体及びホットメルト粘着剤 |
| KR102398069B1 (ko) * | 2019-10-16 | 2022-05-16 | 코제노벨머티얼리스코리아 주식회사 | 경화성 조성물 |
| US11981843B2 (en) * | 2019-11-15 | 2024-05-14 | Lg Chem, Ltd. | Protection film having variable adhesion for foldable display and foldable display device comprising same |
| WO2021193280A1 (ja) * | 2020-03-24 | 2021-09-30 | 三菱ケミカル株式会社 | 化合物および前記化合物を含む重合体組成物 |
| CN112831007B (zh) * | 2021-02-01 | 2022-04-22 | 西北工业大学 | 一种具有多相结构的自修复聚丙烯酸酯弹性体及制备方法 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02248482A (ja) * | 1989-03-23 | 1990-10-04 | Fujikura Kasei Co Ltd | 光硬化性感圧接着剤組成物 |
| TW221061B (https=) * | 1991-12-31 | 1994-02-11 | Minnesota Mining & Mfg | |
| US6902740B2 (en) * | 2001-07-09 | 2005-06-07 | 3M Innovative Properties Company | Pyrrolidonoethyl (meth)acrylate containing pressure sensitive adhesive compositions |
| DE102005045458A1 (de) | 2005-09-22 | 2007-03-29 | Röhm Gmbh | Verfahren zur Herstellung von ABA-Triblockcopolymeren auf (Meth)acrylatbasis |
| DE102006015846A1 (de) | 2006-04-03 | 2007-10-04 | Röhm Gmbh | Kupferentfernung aus ATRP-Produkten mittels Zugabe von Schwefelverbindungen |
| DE102006035726A1 (de) | 2006-07-28 | 2008-01-31 | Evonik Röhm Gmbh | Verfahren zur Herstellung von ABA-Triblockcopolymeren auf (Meth)acrylatbasis |
| DE102006037352A1 (de) | 2006-08-09 | 2008-02-14 | Evonik Röhm Gmbh | Verfahren zur Herstellung von säureterminierten ATRP-Produkten |
| DE102006037351A1 (de) | 2006-08-09 | 2008-02-14 | Evonik Röhm Gmbh | Verfahren zur Herstellung von hydroxytelecheler ATRP-Produkten |
| DE102006037350A1 (de) | 2006-08-09 | 2008-02-14 | Evonik Röhm Gmbh | Verfahren zur Herstellung von halogenfreien ATRP-Produkten |
| DE102006048154A1 (de) | 2006-10-10 | 2008-04-17 | Evonik Röhm Gmbh | Verfahren zur Herstellung von silyltelechelen Polymeren |
| DE102007006105A1 (de) | 2007-02-02 | 2008-08-07 | Evonik Röhm Gmbh | Verfahren zur Herstellung telecheler Polymere |
| DE102007039535A1 (de) | 2007-08-21 | 2009-02-26 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Pentablockcopolymeren mit OH-funktionalisierten Blöcken auf (Meth)acrylatbasis |
| EP2193159A1 (de) | 2007-09-27 | 2010-06-09 | Evonik Goldschmidt GmbH | Polysiloxan blockcopolymere |
| DE102008002016A1 (de) | 2008-05-28 | 2009-12-03 | Evonik Röhm Gmbh | Verfahren zur Herstellung von silyl-funktionalisierten ABA-Triblockcopolymeren auf (Meth)acrylatbasis |
| EP2291412B1 (en) * | 2008-06-18 | 2013-07-24 | Henkel Corporation | Apparatus and methods for controlled radical polymerization |
| DE102008034106A1 (de) | 2008-07-21 | 2010-01-28 | Evonik Röhm Gmbh | Blockcopolymere auf (Meth)acrylatbasis mit A-P-Struktur |
| DE102008043674A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Telechelen mit einer bimodalen Molekulkargewichtsverteilung |
| DE102008043662A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Telechelen mit breiter Molekulargewichtsverteilung |
| DE102008043658A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von AB-Diblockcopolymeren mit einem breit verteilten A-Block |
| DE102008043668A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von ABA-Triblockcopolymeren mit einem bimodalen B-Block |
| DE102008043666A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von AB-Diblockcopolymeren mit einem bimodalen verteilten A-Block |
| US20110213091A1 (en) | 2008-11-12 | 2011-09-01 | Evonik Roehm Gmbh | Method for producing telechelics having a bimodal molecular weight distribution |
| DE102008043669A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von ABA-Triblockcopolymeren mit einem breit verteilten B-Block |
| WO2011119272A2 (en) * | 2010-03-22 | 2011-09-29 | Henkel Corporation | Macro-photoinitiators and curable compositions thereof |
| EP2596062B1 (en) * | 2010-07-23 | 2019-09-18 | Rohm and Haas Company | Set-lrp polymerization of acrylates in the presence of acids |
| US8436094B2 (en) * | 2010-08-25 | 2013-05-07 | Henkel Corporation | Curable compositions with moisture-curable functionality clusters near the chain ends |
| EP2500367A1 (en) * | 2011-03-18 | 2012-09-19 | Henkel AG & Co. KGaA | Block-copolymer containing crosslinkable photoinitator groups |
| CA2849071C (en) * | 2011-09-19 | 2016-05-03 | Henkel US IP LLC | Highly functionalized resin blends |
| CN102796226B (zh) * | 2012-08-25 | 2013-10-02 | 鲁东大学 | 一种棉花纤维素大分子引发剂制备高吸油性树脂的方法 |
| CN102850474B (zh) * | 2012-09-28 | 2014-07-16 | 江西科技师范大学 | 单电子转移活性自由基乳液聚合聚甲基丙烯酸甲酯的方法 |
| US9006362B2 (en) * | 2012-10-16 | 2015-04-14 | Henkel IP & Holding GmbH | Controlled radical polymerization of (meth)acrylate monomers |
| EP2935348A4 (en) | 2012-12-18 | 2016-06-29 | Henkel IP & Holding GmbH | METHOD FOR CONTROLLED RADICAL POLYMERIZATION OF BRANCHED POLYACRYLATES |
| US8883941B2 (en) * | 2013-03-18 | 2014-11-11 | Henkel Corporation | Methods and apparatus for controlled single electron transfer living radical polymerization |
| CN103275283B (zh) * | 2013-04-11 | 2015-08-05 | 河北工业大学 | 一种单电子转移-活性自由基聚合制备聚丙烯酸酯的方法 |
-
2014
- 2014-12-15 US US14/570,060 patent/US9587062B2/en active Active
-
2015
- 2015-12-15 EP EP15870827.1A patent/EP3233940B1/en active Active
- 2015-12-15 JP JP2017550098A patent/JP6689875B2/ja active Active
- 2015-12-15 WO PCT/US2015/065660 patent/WO2016100251A1/en not_active Ceased
- 2015-12-15 CN CN201580073779.2A patent/CN107207653B/zh active Active
- 2015-12-15 BR BR112017012639A patent/BR112017012639A2/pt not_active Application Discontinuation
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