JP6949099B2 - ポリマー材料及び制御ラジカル開始剤を使用した製造方法 - Google Patents
ポリマー材料及び制御ラジカル開始剤を使用した製造方法 Download PDFInfo
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- JP6949099B2 JP6949099B2 JP2019500836A JP2019500836A JP6949099B2 JP 6949099 B2 JP6949099 B2 JP 6949099B2 JP 2019500836 A JP2019500836 A JP 2019500836A JP 2019500836 A JP2019500836 A JP 2019500836A JP 6949099 B2 JP6949099 B2 JP 6949099B2
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- 0 C*NCNC(*)=N Chemical compound C*NCNC(*)=N 0.000 description 10
- YHPFHJSQIJLSHL-UHFFFAOYSA-N CC(C)OC(SC(C(OCC(C(C(F)(F)F)(F)F)(F)F)=O)SC(OC(C)C)=S)=S Chemical compound CC(C)OC(SC(C(OCC(C(C(F)(F)F)(F)F)(F)F)=O)SC(OC(C)C)=S)=S YHPFHJSQIJLSHL-UHFFFAOYSA-N 0.000 description 1
- MNSGBGVWUNQIKL-UHFFFAOYSA-N CCCNC(NCC)=N Chemical compound CCCNC(NCC)=N MNSGBGVWUNQIKL-UHFFFAOYSA-N 0.000 description 1
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- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/026—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising acrylic acid, methacrylic acid or derivatives thereof
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- 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
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/023—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type using a coupling agent
-
- 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
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
-
- 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
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- 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
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
-
- 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
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
-
- 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
- C08F2438/00—Living radical polymerisation
- C08F2438/03—Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662360788P | 2016-07-11 | 2016-07-11 | |
| US62/360,788 | 2016-07-11 | ||
| US201762479547P | 2017-03-31 | 2017-03-31 | |
| US62/479,547 | 2017-03-31 | ||
| PCT/US2017/039368 WO2018013330A1 (en) | 2016-07-11 | 2017-06-27 | Polymeric material and methods of making using controlled radical initiators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019520465A JP2019520465A (ja) | 2019-07-18 |
| JP2019520465A5 JP2019520465A5 (enExample) | 2020-02-20 |
| JP6949099B2 true JP6949099B2 (ja) | 2021-10-13 |
Family
ID=59366491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019500836A Active JP6949099B2 (ja) | 2016-07-11 | 2017-06-27 | ポリマー材料及び制御ラジカル開始剤を使用した製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US10400055B2 (enExample) |
| EP (1) | EP3481872B1 (enExample) |
| JP (1) | JP6949099B2 (enExample) |
| CN (1) | CN109476774B (enExample) |
| WO (1) | WO2018013330A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3559062B1 (en) | 2016-12-22 | 2020-12-02 | 3M Innovative Properties Company | Crosslinkable and crosslinked polymeric materials |
| EP3601390B1 (en) | 2017-03-31 | 2023-05-03 | 3M Innovative Properties Company | Polymeric materials formed using controlled radical initiators |
| CN111556877B (zh) * | 2017-12-19 | 2022-08-23 | 3M创新有限公司 | 使用具有两个含硫代羰基硫基的基团的引发剂形成的聚合物材料 |
| WO2019123182A1 (en) | 2017-12-21 | 2019-06-27 | 3M Innovative Properties Company | Polymeric compositions prepared with a controlled radical initiator |
| WO2019162805A1 (en) | 2018-02-21 | 2019-08-29 | 3M Innovative Properties Company | Ketone-containing controlled radical initiators for polymerization reactions |
| EP3755728A1 (en) * | 2018-02-21 | 2020-12-30 | 3M Innovative Properties Company | Polymeric materials formed using initiators with a ketone group and two thiocarbonylthio-containing groups |
| WO2020128732A2 (en) | 2018-12-19 | 2020-06-25 | 3M Innovative Properties Company | Zwitterionic copolymers, coating compositions, articles, and coating methods |
| WO2020149388A1 (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 |
| 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 |
| CN110357992A (zh) * | 2019-07-09 | 2019-10-22 | 复旦大学 | 一种超高分子量含氟聚合物的制备方法 |
| US11505637B1 (en) | 2019-09-24 | 2022-11-22 | 3M Innovative Properties Company | Block copolymers with a polydiorganosiloxane block and a phosphate or phosphonate containing block |
| US20230026581A1 (en) | 2019-12-19 | 2023-01-26 | 3M Innovative Properties Company | Block copolymers with a fluorinated block and a phosphorus-containing block |
| CN115836095A (zh) | 2020-07-16 | 2023-03-21 | 3M创新有限公司 | 用于毒力抑制的含膦酸酯的聚合物 |
| EP4130077A1 (en) * | 2021-08-06 | 2023-02-08 | Clariant International Ltd | Symmetric raft agent for controlled radical polymerization of multi-block copolymers for monomers with different activities |
| WO2023037185A1 (en) | 2021-09-13 | 2023-03-16 | 3M Innovative Properties Company | (meth)acrylic-epoxy uv initiated adhesive compositions and adhesive-containing articles |
| EP4602109A1 (en) | 2022-10-10 | 2025-08-20 | 3M Innovative Properties Company | Electrically debondable uv activated adhesives |
| WO2025083620A1 (en) | 2023-10-20 | 2025-04-24 | 3M Innovative Properties Company | Tape including a curable adhesive film and related adhesive system and method |
| WO2025181577A1 (en) | 2024-02-29 | 2025-09-04 | 3M Innovative Properties Company | Curable adhesive composition comprising epoxy, initiator and metal compound, articles and methods |
| WO2025215476A1 (en) | 2024-04-10 | 2025-10-16 | 3M Innovative Properties Company | Adhesives comprising epoxy and (meth)acrylic polymer comprising toughening agent |
| WO2025215510A1 (en) | 2024-04-10 | 2025-10-16 | 3M Innovative Properties Company | Adhesives comprising epoxy and (meth)acrylic polymer comprising polymerized (meth) acryl macromer |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US2067494A (en) | 1932-04-05 | 1937-01-12 | Wingfoot Corp | Dithiocarbamates |
| US2716633A (en) | 1954-07-22 | 1955-08-30 | Du Pont | Polymerizable compositions |
| CA677797A (en) | 1955-11-18 | 1964-01-14 | Minnesota Mining And Manufacturing Company | Sheet material having a pressure-sensitive adhesive coating of acrylate ester copolymer |
| US3239478A (en) | 1963-06-26 | 1966-03-08 | Shell Oil Co | Block copolymer adhesive compositions and articles prepared therefrom |
| GB1038727A (en) * | 1964-02-13 | 1966-08-10 | Monsanto Chemicals | Vulcanisation process and novel bis(dithiocarbamates) for use therein |
| GB1042902A (en) | 1964-02-28 | 1966-09-14 | Monsanto Chemicals | New thiomorpholinocarbodithioic acid derivatives and their use as vulcanisation accelerators |
| US4013638A (en) | 1965-01-18 | 1977-03-22 | Monsanto Company | Azabicyclononanecarbodithioic acid |
| US4181752A (en) | 1974-09-03 | 1980-01-01 | Minnesota Mining And Manufacturing Company | Acrylic-type pressure sensitive adhesives by means of ultraviolet radiation curing |
| US4089857A (en) * | 1976-12-30 | 1978-05-16 | International Business Machines Corporation | Tetrathiapentalene and tetraselenapentalene compounds |
| JPS5846236B2 (ja) | 1980-03-05 | 1983-10-14 | 日東電工株式会社 | 感圧性接着剤組成物 |
| US4554325A (en) | 1984-05-11 | 1985-11-19 | The Dow Chemical Company | Perfluorocarbon based polymeric coatings having low critical surface tensions |
| DE3426087C1 (de) | 1984-07-14 | 1986-03-06 | Th. Goldschmidt Ag, 4300 Essen | acrylsaeureestermodifizierte Organopolysiloxangemische,deren Herstellung und Verwendung als abhaesive Beschichtungsmassen |
| US4798852A (en) | 1985-10-29 | 1989-01-17 | Desoto, Inc. | Ultraviolet curable coatings for optical glass fiber |
| US4908229A (en) | 1986-03-11 | 1990-03-13 | Union Oil Of California | Method for producing an article containing a radiation cross-linked polymer and the article produced thereby |
| US5122567A (en) | 1986-05-02 | 1992-06-16 | Union Oil Company Of California | Pressure sensitive adhesives of acetoacetoxy-alkyl acrylate polymers |
| US5314962A (en) * | 1987-04-07 | 1994-05-24 | Mitsubishi Petrochemical Company Limited | ABA type block copolymers |
| JP2553134B2 (ja) * | 1987-04-07 | 1996-11-13 | 三菱化学株式会社 | Aba型ブロック共重合体 |
| US4812541A (en) | 1987-12-23 | 1989-03-14 | Avery International Corporation | High performance pressure-sensitive adhesive polymers |
| AU614140B2 (en) | 1988-06-28 | 1991-08-22 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesive |
| US5274063A (en) | 1990-12-26 | 1993-12-28 | Kyoeisha Chemical Co., Ltd. | Vinyl polymer having (meth)acryloyl groups on the side chains and method for preparing same |
| EP0633918A1 (en) * | 1992-03-31 | 1995-01-18 | Minnesota Mining And Manufacturing Company | Ultraviolet radiation curable acrylate pressure-sensitive adhesive compositions |
| CA2192447A1 (en) | 1994-07-08 | 1996-01-25 | Robert John Barsotti | Coating compositions with branched polymer |
| US5576388A (en) | 1994-10-11 | 1996-11-19 | Shell Oil Company | Telechelic polymers and heterotelechelic polydiene block polymers with dual cure systems |
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| US5804301A (en) | 1996-01-11 | 1998-09-08 | Avery Dennison Corporation | Radiation-curable coating compositions |
| JPH1030078A (ja) | 1996-04-24 | 1998-02-03 | Sekisui Chem Co Ltd | 接着性組成物及び塗工方法 |
| CA2259559C (en) | 1996-07-10 | 2004-11-09 | E.I. Du Pont De Nemours And Company | Polymerization with living characteristics |
| FR2764892B1 (fr) | 1997-06-23 | 2000-03-03 | Rhodia Chimie Sa | Procede de synthese de polymeres a blocs |
| US5907024A (en) | 1997-11-12 | 1999-05-25 | Basf Corporation | High solids thermosetting compositions with dual cure mechanism |
| EP1591507A3 (en) | 1998-12-29 | 2006-01-25 | Minnesota Mining And Manufacturing Company | Block copolymer hot-melt processable adhesives |
| EP2082995B1 (en) | 1999-10-27 | 2012-08-08 | 3M Innovative Properties Company | Method of reducing the surface tension, of forming a stable foam and to increase the wetting of a coating |
| FR2812296B1 (fr) * | 2000-07-25 | 2002-12-20 | Rhodia Chimie Sa | Procede de synthese de copolymeres hybrides et organiques par polymerisation radicalaire controlee |
| JP3971705B2 (ja) | 2001-04-04 | 2007-09-05 | 株式会社カネカ | 熱可塑性樹脂組成物およびエラストマー組成物 |
| US6747104B1 (en) | 2003-03-21 | 2004-06-08 | 3M Innovative Properties Company | Azlactone photoiniferters for radical polymerization |
| US6753391B1 (en) | 2003-05-05 | 2004-06-22 | 3M Innovative Properties Company | Ring-opened azlactone chain transfer agents for radical polymerization |
| US6762257B1 (en) | 2003-05-05 | 2004-07-13 | 3M Innovative Properties Company | Azlactone chain transfer agents for radical polymerization |
| US7255920B2 (en) | 2004-07-29 | 2007-08-14 | 3M Innovative Properties Company | (Meth)acrylate block copolymer pressure sensitive adhesives |
| CN102770465B (zh) * | 2010-03-22 | 2015-04-22 | 汉高美国知识产权有限责任公司 | 大分子光引发剂及其可固化组合物 |
| US8137807B2 (en) | 2010-03-26 | 2012-03-20 | 3M Innovative Properties Company | Pressure-sensitive adhesives derived from 2-alkyl alkanols |
| DE102011086502A1 (de) | 2011-11-16 | 2013-05-16 | Tesa Se | Verfahren zur Herstellung ungefärbter Polyacrylatklebemassen mit enger Molmassenverteilung |
| DE102011086503A1 (de) | 2011-11-16 | 2013-05-16 | Tesa Se | Verfahren zur Herstellung von kohäsiven Polyacrylatklebemassen mit enger Molmassenverteilung |
| DE102011089367A1 (de) | 2011-12-21 | 2013-06-27 | Tesa Se | Haftklebemassen mit hohen Molmassen und enger Molmassenverteilung und Verfahren zu deren Herstellung |
| EP3559062B1 (en) | 2016-12-22 | 2020-12-02 | 3M Innovative Properties Company | Crosslinkable and crosslinked polymeric materials |
-
2017
- 2017-06-27 EP EP17740824.2A patent/EP3481872B1/en active Active
- 2017-06-27 CN CN201780042617.1A patent/CN109476774B/zh active Active
- 2017-06-27 JP JP2019500836A patent/JP6949099B2/ja active Active
- 2017-06-27 US US16/314,760 patent/US10400055B2/en active Active
- 2017-06-27 WO PCT/US2017/039368 patent/WO2018013330A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20190153142A1 (en) | 2019-05-23 |
| WO2018013330A1 (en) | 2018-01-18 |
| JP2019520465A (ja) | 2019-07-18 |
| EP3481872A1 (en) | 2019-05-15 |
| US10400055B2 (en) | 2019-09-03 |
| CN109476774B (zh) | 2021-01-12 |
| CN109476774A (zh) | 2019-03-15 |
| EP3481872B1 (en) | 2020-04-08 |
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