JP6722581B2 - 接着促進剤、それを含有してなる硬化性オルガノポリシロキサン組成物 - Google Patents
接着促進剤、それを含有してなる硬化性オルガノポリシロキサン組成物 Download PDFInfo
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- JP6722581B2 JP6722581B2 JP2016512585A JP2016512585A JP6722581B2 JP 6722581 B2 JP6722581 B2 JP 6722581B2 JP 2016512585 A JP2016512585 A JP 2016512585A JP 2016512585 A JP2016512585 A JP 2016512585A JP 6722581 B2 JP6722581 B2 JP 6722581B2
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- curable organopolysiloxane
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- 0 CCC(N*1OC(C)C*(C)CCC1)N=C Chemical compound CCC(N*1OC(C)C*(C)CCC1)N=C 0.000 description 2
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- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
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- 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
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
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- 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
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/549—Silicon-containing compounds containing silicon in a ring
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
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- 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
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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- 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
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- 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
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
- C09K3/1018—Macromolecular compounds having one or more carbon-to-silicon linkages
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
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- 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
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
Description
ルガノポリシロキサン組成物は、上記の成分(A)〜(C)を含有する接着促進剤を含有しているので、アルミダイキャストや有機樹脂材料に対して、優れた接着性を示す。このことを利用して、本発明の硬化性オルガノポリシロキサン組成物は、過酷な環境下で使用した場合であっても、接着耐久性と接着強度に優れ、電気・電子部品の信頼性・耐久性を長期間に渡って維持することを可能とする、電気・電子部品の保護剤または接着剤組成物として利用することができる。
のアルケニル基;フェニル基、トリル基、キシリル基、およびナフチル基等のアリール基;ベンジル基、フェネチル基、およびフェニルプロピル基等のアラルキル基;並びに、3−クロロプロピル基および3,3,3−トリフロロプロピル基等のハロゲン化アルキル基が挙げられ、好ましくは、アルキル基、シクロアルキル基、アルケニル基、またはアリール基であり、より好ましくは、メチル基、ビニル基、またはフェニル基である。特に、成分(E)は任意で、平均0.5個以上のアルケニル基を有するものであってよく、当該オルガノポリシロキサン組成物がヒドロシリル化反応により硬化する場合には、アルケニル基を有することが好ましい。この場合、アルケニル基としては、ビニル基、アリル基、ブテニル基、ペンテニル基、ヘキセニル基が例示され、好ましくは、ビニル基である。
<接着促進剤の各成分>
(A1)カルバシラトラン:下式で示されるシラトラン誘導体
(B1)HMSH:1,6−ビス(トリメトキシシリル)ヘキサン
(C1)Epシラン:3−グリシドキシプロピルトリメトキシシラン
<反応性官能基を有するオルガノポリシロキサン>
(G1−1)Vi両末端シロキサン(1):
分子鎖両末端ジメチルビニルシロキシ基封鎖ジメチルポリシロキサン (粘度 40,000mPa・s,Vi含有量 0.08質量%)
(G1−2)Vi両末端シロキサン(2):
分子鎖両末端ジメチルビニルシロキシ基封鎖ジメチルポリシロキサン (粘度 2,000mPa・s,Vi含有量 0.23質量%)
(G1−3)Viシロキサンレジン:
(CH2=CH(CH3)2SiO0.5)4((CH3)3SiO0.5)40(SiO2.0)56 で示される、Vi含有量0.68質量%、重量平均分子量20,000のシロキサンレジン
(G2−1)SiHシロキサン:
分子鎖両末端トリメチルシロキシ基封鎖メチルハイドロジェンシロキサン・ジメチルシロキサン共重合体 (粘度 5mPa・s, Si−H 含有量 0.72質量%)
<硬化触媒>
(D1)Pt錯体:白金の1,3−ジビニル−1,1,3,3−テトラメチルジシロキサン錯体(本組成物中のオルガノポリシロキサン成分の合計に対して、白金金属が質量単位で表1に示す各ppmとなる量)
(D2)Ti縮合触媒:ジ(イソプロポキシ)ビス(エチルアセトアセテート)チタン
<補強性充填剤>
(F1)石英微粉末: 平均粒子径(d50)が1.7μmの石英粉末
(F2)ヒュームドシリカ: ヘキサメチルジシラザンにより表面処理されたヒュームドシリカ(表面積130m2/g)
<下式で示されるアルコキシシリル含有基を有するオルガノポリシロキサン等>
(E1))両末端変性ポリシロキサン: 分子鎖の両末端に前記のアルコキシシリル含有基を有するジメチルポリシロキサン(粘度40,000mPa・s)
(E2)両末端変性ポリシロキサン: 分子鎖の両末端に前記のアルコキシシリル含有基を有するジメチルポリシロキサン(粘度10,000mPa・s)
(E3)片末端変性ポリ(Vi)シロキサン:分子鎖の片末端のみに前記のアルコキシシリル含有基を有し、他の末端がジメチルビニルシロキシ基で封鎖されたジメチルシロキサン・メチルビニルシロキサン共重合体(粘度40,000mPa・s、Vi含有量0.04質量%)
(E4)片末端変性ポリ(Vi)シロキサン:分子鎖の片末端のみに前記のアルコキシシリル含有基を有し、他の末端がジメチルビニルシロキシ基で封鎖されたジメチルシロキサン・メチルビニルシロキサン共重合体(粘度10,000mPa・s、Vi含有量0.06質量%)
<硬化抑制剤>
ETCH:1−エチニルシクロヘキサノール
Claims (6)
- 次の(A)、(B)、(C)を所定の相対量含有する接着促進剤を含むヒドロシリル化反応硬化性オルガノポリシロキサン組成物:
(A) アミノ基含有オルガノアルコキシシランとエポキシ基含有オルガノアルコキシシランとの反応混合物であり、一般式[化1]:
で表される同じかまたは異なる基であり、R3は同じかまたは異なる水素原子もしくはアルキル基である。}で示されるカルバシラトラン誘導体 100質量部、
(B)一般式[化3]:
(C) 一般式[化4]:
- さらに、(D)ヒドロシリル化反応触媒を含有する、請求項1に記載のヒドロシリル化反応硬化性オルガノポリシロキサン組成物。
- (F)成分が、ヒュームドシリカ微粉末、沈降性シリカ微粉末、焼成シリカ微粉末、ヒュームド酸化チタン微粉末、および石英微粉末からなる群より選択される少なくとも一種の補強性充填剤である、請求項3に記載のヒドロシリル化反応硬化性オルガノポリシロキサン組成物。
- 請求項1〜4のいずれか1項に記載のヒドロシリル化反応硬化性オルガノポリシロキサン組成物を含む電気・電子部品の保護剤または接着剤組成物。
- 電気・電子部品が請求項5に記載の保護剤または接着剤組成物により封止またはシールされてなる電気・電子機器。
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Application Number | Priority Date | Filing Date | Title |
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JP2014079877 | 2014-04-09 | ||
JP2014079877 | 2014-04-09 | ||
PCT/JP2015/001763 WO2015155949A1 (ja) | 2014-04-09 | 2015-03-26 | 接着促進剤、それを含有してなる硬化性オルガノポリシロキサン組成物 |
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JPWO2015155949A1 JPWO2015155949A1 (ja) | 2017-04-13 |
JP6722581B2 true JP6722581B2 (ja) | 2020-07-15 |
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Country | Link |
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US (1) | US10358542B2 (ja) |
EP (1) | EP3130632B1 (ja) |
JP (1) | JP6722581B2 (ja) |
KR (1) | KR102322935B1 (ja) |
CN (1) | CN106459492B (ja) |
TW (1) | TWI677550B (ja) |
WO (1) | WO2015155949A1 (ja) |
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US20220002594A1 (en) * | 2018-10-18 | 2022-01-06 | Dow Toray Co., Ltd. | Curable silicone composition and cured product thereof, layered product and production method therefor, and optical device or optical display |
EP3986967A4 (en) * | 2019-06-21 | 2023-01-25 | Dow Silicones Corporation | METHOD FOR PRODUCING A THIXOTROPIC CURING SILICONE COMPOSITION |
KR20220024580A (ko) * | 2019-06-21 | 2022-03-03 | 다우 실리콘즈 코포레이션 | 열 전도성 실리콘 조성물 |
CN110256974A (zh) * | 2019-07-19 | 2019-09-20 | 广州市高士实业有限公司 | 一种硅烷改性聚醚密封胶及其制备方法与应用 |
CN114144477B (zh) * | 2019-07-26 | 2023-02-28 | 美国陶氏有机硅公司 | 可固化有机聚硅氧烷组合物、固化产物和电气/电子设备 |
CN110994031B (zh) * | 2019-12-19 | 2021-11-30 | 湖南美尼科技有限公司 | 一种快充耐高温电解液及制备方法 |
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JPS528854B2 (ja) | 1972-01-13 | 1977-03-11 | ||
JPS5480358A (en) | 1977-12-08 | 1979-06-27 | Shin Etsu Chem Co Ltd | Curable organopolysiloxane composition |
US4711928A (en) | 1986-03-03 | 1987-12-08 | Dow Corning Corporation | Moisture cured one-part RTV silicone sealant |
US4871827A (en) | 1986-03-03 | 1989-10-03 | Dow Corning Corporation | Method of improving shelf life of silicone elastomeric sealant |
JPH07113083B2 (ja) | 1987-08-28 | 1995-12-06 | 東レ・ダウコーニング・シリコーン株式会社 | 室温硬化性オルガノポリシロキサン組成物 |
JPH04222871A (ja) | 1990-12-25 | 1992-08-12 | Toray Dow Corning Silicone Co Ltd | 硬化性オルガノポリシロキサン組成物 |
JP3831481B2 (ja) | 1996-11-18 | 2006-10-11 | 東レ・ダウコーニング株式会社 | カルバシラトラン誘導体、その製造方法、接着促進剤、および硬化性シリコーン組成物 |
JPH1160952A (ja) * | 1997-08-21 | 1999-03-05 | Toray Dow Corning Silicone Co Ltd | シリコーンゴム組成物 |
JP2001261963A (ja) * | 2000-03-17 | 2001-09-26 | Dow Corning Toray Silicone Co Ltd | シリコーンゴム組成物 |
JP2002170978A (ja) | 2000-11-30 | 2002-06-14 | Sanyo Electric Co Ltd | 太陽電池モジュール,端子箱及び太陽電池モジュールの接続方法 |
JP2003221506A (ja) | 2002-01-31 | 2003-08-08 | Dow Corning Toray Silicone Co Ltd | 室温硬化性オルガノポリシロキサン組成物 |
US8481668B2 (en) | 2005-09-16 | 2013-07-09 | Momentive Performance Materials Inc. | Silane-containing adhesion promoter composition and sealants, adhesives and coatings containing same |
TW200716710A (en) * | 2005-09-30 | 2007-05-01 | Dow Corning Toray Co Ltd | Multi-component room-temperature curable silicone rubber composition |
JP2007235013A (ja) | 2006-03-03 | 2007-09-13 | Denso Corp | 電子回路基板の防水構造 |
JP4646260B2 (ja) | 2008-12-02 | 2011-03-09 | 古河電気工業株式会社 | 端子付自動車ハーネス |
JP2012017427A (ja) * | 2010-07-09 | 2012-01-26 | Dow Corning Toray Co Ltd | 多成分型室温硬化性シリコーンゴム組成物 |
JP5887786B2 (ja) * | 2010-10-27 | 2016-03-16 | セメダイン株式会社 | 硬化性組成物 |
JP2012204016A (ja) | 2011-03-23 | 2012-10-22 | Sumitomo Wiring Syst Ltd | 電線の止水方法および電線の止水構造 |
FR3007817B1 (fr) | 2013-06-28 | 2015-07-17 | Staubli Sa Ets | Element femelle de raccord rapide et raccord rapide comprenant un tel element |
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- 2015-03-26 JP JP2016512585A patent/JP6722581B2/ja active Active
- 2015-03-26 WO PCT/JP2015/001763 patent/WO2015155949A1/ja active Application Filing
- 2015-03-26 KR KR1020167031210A patent/KR102322935B1/ko active IP Right Grant
- 2015-03-26 CN CN201580023744.8A patent/CN106459492B/zh active Active
- 2015-03-26 EP EP15776667.6A patent/EP3130632B1/en active Active
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Also Published As
Publication number | Publication date |
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KR20160143781A (ko) | 2016-12-14 |
WO2015155949A1 (ja) | 2015-10-15 |
EP3130632A1 (en) | 2017-02-15 |
TWI677550B (zh) | 2019-11-21 |
US10358542B2 (en) | 2019-07-23 |
TW201542741A (zh) | 2015-11-16 |
EP3130632A4 (en) | 2017-11-08 |
CN106459492B (zh) | 2020-05-08 |
JPWO2015155949A1 (ja) | 2017-04-13 |
US20170058103A1 (en) | 2017-03-02 |
EP3130632B1 (en) | 2022-03-30 |
KR102322935B1 (ko) | 2021-11-10 |
CN106459492A (zh) | 2017-02-22 |
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