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 (enExample) | 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 (enExample) |
| EP (1) | EP3233940B1 (enExample) |
| JP (1) | JP6689875B2 (enExample) |
| CN (1) | CN107207653B (enExample) |
| BR (1) | BR112017012639A2 (enExample) |
| WO (1) | WO2016100251A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6808746B2 (ja) | 2016-02-19 | 2021-01-06 | アベリー・デニソン・コーポレイションＡｖｅｒｙ Ｄｅｎｎｉｓｏｎ Ｃｏｒｐｏｒａｔｉｏｎ | 接着剤を製造する２段階の方法及び関連組成物 |
| FR3047991B1 (fr) * | 2016-02-24 | 2020-03-20 | Arkema France | Composition polymerisable de faible viscosite precurseur de materiaux renforces a l'impact |
| EP4790115A2 (en) * | 2016-10-25 | 2026-08-12 | Avery Dennison Corporation | Block polymers with photoinitiator groups in backbone and their use in adhesive compositions |
| JP7507088B2 (ja) | 2017-12-19 | 2024-06-27 | エイブリィ・デニソン・コーポレイション | ペンダント官能基の後重合官能化 |
| KR102203870B1 (ko) | 2018-04-12 | 2021-01-18 | 주식회사 엘지화학 | 임시고정용 점착시트 및 이를 사용한 반도체 장치의 제조 방법 |
| JP7392401B2 (ja) * | 2018-11-08 | 2023-12-06 | 三菱ケミカル株式会社 | 粘着剤樹脂組成物、粘着シート、活性エネルギー線硬化性粘着シート、光学部材、画像表示装置用積層体及び画像表示装置 |
| JPWO2020149385A1 (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 |
| WO2020149387A1 (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その製造方法並びに伸縮性部材 |
| WO2021075901A1 (ko) * | 2019-10-16 | 2021-04-22 | 주식회사 엘지화학 | 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 |
| CN115135677B (zh) * | 2020-03-24 | 2025-04-29 | 三菱化学株式会社 | 化合物和含所述化合物的聚合物组合物 |
| 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 (enExample) * | 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 |
| CA2730262C (en) * | 2008-06-18 | 2015-06-09 | 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 |
| DE102008043668A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von ABA-Triblockcopolymeren mit einem bimodalen B-Block |
| US20110213091A1 (en) | 2008-11-12 | 2011-09-01 | Evonik Roehm Gmbh | Method for producing telechelics having a bimodal molecular weight distribution |
| DE102008043658A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von AB-Diblockcopolymeren mit einem breit verteilten A-Block |
| DE102008043662A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Telechelen mit breiter Molekulargewichtsverteilung |
| DE102008043669A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von ABA-Triblockcopolymeren mit einem breit verteilten 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 |
| DE102008043674A1 (de) | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Telechelen mit einer bimodalen Molekulkargewichtsverteilung |
| JP5955832B2 (ja) * | 2010-03-22 | 2016-07-20 | ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング | マクロ光開始剤およびそれらの硬化性組成物 |
| WO2012012705A1 (en) * | 2010-07-23 | 2012-01-26 | 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 CN CN201580073779.2A patent/CN107207653B/zh 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 BR BR112017012639A patent/BR112017012639A2/pt not_active Application Discontinuation
- 2015-12-15 EP EP15870827.1A patent/EP3233940B1/en active Active
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