JP2007501312A - コマンド−キュア接着剤 - Google Patents
コマンド−キュア接着剤 Download PDFInfo
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- JP2007501312A JP2007501312A JP2006522625A JP2006522625A JP2007501312A JP 2007501312 A JP2007501312 A JP 2007501312A JP 2006522625 A JP2006522625 A JP 2006522625A JP 2006522625 A JP2006522625 A JP 2006522625A JP 2007501312 A JP2007501312 A JP 2007501312A
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- JP
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- Prior art keywords
- group
- mixture
- oxirane
- oxetane
- irradiation
- Prior art date
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
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- 125000004429 atom Chemical group 0.000 claims description 3
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- LUKZQXIIABXJOH-UHFFFAOYSA-N 2-(2,2-dimethylpropoxymethyl)oxirane Chemical compound CC(C)(C)COCC1CO1 LUKZQXIIABXJOH-UHFFFAOYSA-N 0.000 description 1
- QNYBOILAKBSWFG-UHFFFAOYSA-N 2-(phenylmethoxymethyl)oxirane Chemical compound C1OC1COCC1=CC=CC=C1 QNYBOILAKBSWFG-UHFFFAOYSA-N 0.000 description 1
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- JUXZNIDKDPLYBY-UHFFFAOYSA-N 3-ethyl-3-(phenoxymethyl)oxetane Chemical compound C=1C=CC=CC=1OCC1(CC)COC1 JUXZNIDKDPLYBY-UHFFFAOYSA-N 0.000 description 1
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 1
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- MUBKMWFYVHYZAI-UHFFFAOYSA-N [Al].[Cu].[Zn] Chemical compound [Al].[Cu].[Zn] MUBKMWFYVHYZAI-UHFFFAOYSA-N 0.000 description 1
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- 125000003342 alkenyl group Chemical group 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/18—Oxetanes
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- 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
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
- C09J171/02—Polyalkylene oxides
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
-
- 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
- Y10T156/00—Adhesive bonding and miscellaneous chemical manufacture
- Y10T156/10—Methods of surface bonding and/or assembly therefor
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
- Polyethers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49235203P | 2003-08-04 | 2003-08-04 | |
| US10/700,318 US7235593B2 (en) | 2003-08-04 | 2003-10-31 | Command-cure adhesives |
| PCT/US2004/024583 WO2005016989A1 (en) | 2003-08-04 | 2004-07-29 | Command-cure adhesives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007501312A true JP2007501312A (ja) | 2007-01-25 |
| JP2007501312A5 JP2007501312A5 (https=) | 2007-09-13 |
Family
ID=34197942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006522625A Pending JP2007501312A (ja) | 2003-08-04 | 2004-07-29 | コマンド−キュア接着剤 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7235593B2 (https=) |
| EP (1) | EP1651700B1 (https=) |
| JP (1) | JP2007501312A (https=) |
| CA (1) | CA2534635C (https=) |
| WO (1) | WO2005016989A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016000801A (ja) * | 2014-05-21 | 2016-01-07 | 三菱化学株式会社 | エポキシ樹脂用希釈剤、及びエポキシ樹脂組成物 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010077606A1 (en) * | 2008-12-08 | 2010-07-08 | Rensselaer Polytechnic Institute | Redox-initiated cationic polymerization using vapor-state reducing agents |
| KR101073698B1 (ko) * | 2009-09-07 | 2011-10-14 | 도레이첨단소재 주식회사 | 점착테이프와 리드프레임의 라미네이션 방법 |
| US8828542B2 (en) * | 2010-02-26 | 2014-09-09 | Korea University Research And Business Foundation | Nanoparticles |
| JP5629009B2 (ja) | 2010-09-15 | 2014-11-19 | ヘンケル アイルランド リミテッド | 二成分系シアノアクリレート／カチオン硬化性接着剤システム |
| CN105073849A (zh) | 2012-12-11 | 2015-11-18 | 粘合剂研究股份有限公司 | 反应性膜粘合剂 |
| US8981027B2 (en) | 2013-03-15 | 2015-03-17 | Henkel IP & Holding GmbH | Two-part, cyanoacrylate/cationically curable adhesive systems |
| TWI519560B (zh) | 2014-11-24 | 2016-02-01 | 財團法人工業技術研究院 | 含氧雜環丁烷基與環氧基之樹脂與樹脂組成物 |
| PL3253341T3 (pl) | 2015-02-02 | 2019-06-28 | Coloplast A/S | Urządzenie stomijne |
| DK3280368T3 (da) | 2015-04-10 | 2019-09-23 | Coloplast As | Stomianordning |
| EP3106893A3 (en) | 2015-05-28 | 2017-03-15 | The Royal Institution for the Advancement of Learning / McGill University | Methods of designing mri rf coils |
| US9926476B2 (en) * | 2016-04-22 | 2018-03-27 | Addison Clear Wave Coatings Inc. | Dual cure epoxy adhesives |
| US12344703B2 (en) | 2020-01-27 | 2025-07-01 | Hitachi Energy Ltd | Photo radiation curable epoxy for electrical components |
| CN114507479B (zh) * | 2020-11-16 | 2023-12-15 | 常州强力先端电子材料有限公司 | 光固化组合物、粘结剂及其制备方法、基材的粘结方法 |
| CN114507416A (zh) * | 2020-11-16 | 2022-05-17 | 常州强力先端电子材料有限公司 | 光固化组合物、涂料及其制备方法、碳纤维预浸料及其制备方法和纤维复合材料 |
| US12415942B2 (en) | 2021-10-22 | 2025-09-16 | Nano And Advanced Materials Institute Limited | Light or heat triggered frontally cured cure-on-demand adhesives kit |
| WO2024220663A2 (en) * | 2023-04-21 | 2024-10-24 | Nanotech Energy, Inc. | Conductive adhesives and epoxies |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4289595A (en) * | 1979-11-26 | 1981-09-15 | American Can Company | Ambient temperature curing photopolymerizable epoxide compositions utilizing epoxide ethers and methods |
| US5144051A (en) * | 1990-05-29 | 1992-09-01 | Minnesota Mining And Manufacturing Company | Branched alkoxyphenyl iodonium salt photoinitiators |
| JPH07503270A (ja) * | 1992-01-22 | 1995-04-06 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | エネルギー重合性接着剤，塗料，フィルム，およびその製造法 |
| JP2001181221A (ja) * | 1999-12-21 | 2001-07-03 | Ciba Specialty Chem Holding Inc | 潜伏性酸供与体としてのヨードニウム塩 |
| JP2001279215A (ja) * | 2000-03-24 | 2001-10-10 | Three M Innovative Properties Co | 異方導電性接着剤組成物およびそれから形成された異方導電性接着フィルム |
| JP2003020452A (ja) * | 2001-06-19 | 2003-01-24 | Three M Innovative Properties Co | 紫外線活性化型接着フィルムを用いた基材接着方法及び紫外線照射装置 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH452201A (de) * | 1965-04-01 | 1968-05-31 | Ciba Geigy | Verfahren zur Herstellung von neuen Oxetangruppen enthaltenden Polymerisaten |
| US3457193A (en) * | 1965-06-30 | 1969-07-22 | Union Carbide Corp | Epoxyoxacyclobutanes and polymers thereof |
| US4717605A (en) * | 1984-05-16 | 1988-01-05 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Radiation curable adhesives |
| US5463084A (en) * | 1992-02-18 | 1995-10-31 | Rensselaer Polytechnic Institute | Photocurable silicone oxetanes |
-
2003
- 2003-10-31 US US10/700,318 patent/US7235593B2/en not_active Expired - Lifetime
-
2004
- 2004-07-29 WO PCT/US2004/024583 patent/WO2005016989A1/en not_active Ceased
- 2004-07-29 EP EP04779597.6A patent/EP1651700B1/en not_active Expired - Lifetime
- 2004-07-29 CA CA2534635A patent/CA2534635C/en not_active Expired - Lifetime
- 2004-07-29 JP JP2006522625A patent/JP2007501312A/ja active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4289595A (en) * | 1979-11-26 | 1981-09-15 | American Can Company | Ambient temperature curing photopolymerizable epoxide compositions utilizing epoxide ethers and methods |
| US5144051A (en) * | 1990-05-29 | 1992-09-01 | Minnesota Mining And Manufacturing Company | Branched alkoxyphenyl iodonium salt photoinitiators |
| JPH07503270A (ja) * | 1992-01-22 | 1995-04-06 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | エネルギー重合性接着剤，塗料，フィルム，およびその製造法 |
| JP2001181221A (ja) * | 1999-12-21 | 2001-07-03 | Ciba Specialty Chem Holding Inc | 潜伏性酸供与体としてのヨードニウム塩 |
| JP2001279215A (ja) * | 2000-03-24 | 2001-10-10 | Three M Innovative Properties Co | 異方導電性接着剤組成物およびそれから形成された異方導電性接着フィルム |
| JP2003020452A (ja) * | 2001-06-19 | 2003-01-24 | Three M Innovative Properties Co | 紫外線活性化型接着フィルムを用いた基材接着方法及び紫外線照射装置 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016000801A (ja) * | 2014-05-21 | 2016-01-07 | 三菱化学株式会社 | エポキシ樹脂用希釈剤、及びエポキシ樹脂組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20050092428A1 (en) | 2005-05-05 |
| US7235593B2 (en) | 2007-06-26 |
| CA2534635C (en) | 2011-08-16 |
| EP1651700B1 (en) | 2014-04-16 |
| WO2005016989A1 (en) | 2005-02-24 |
| CA2534635A1 (en) | 2005-02-24 |
| EP1651700A1 (en) | 2006-05-03 |
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