JP6585045B2 - アルコキシシラン官能化ポリアクリレート組成物およびその調製方法。 - Google Patents
アルコキシシラン官能化ポリアクリレート組成物およびその調製方法。 Download PDFInfo
- Publication number
- JP6585045B2 JP6585045B2 JP2016534584A JP2016534584A JP6585045B2 JP 6585045 B2 JP6585045 B2 JP 6585045B2 JP 2016534584 A JP2016534584 A JP 2016534584A JP 2016534584 A JP2016534584 A JP 2016534584A JP 6585045 B2 JP6585045 B2 JP 6585045B2
- Authority
- JP
- Japan
- Prior art keywords
- aminoalkylalkoxysilane
- alkyl
- carbon atoms
- hydrocarbon compound
- functionalized hydrocarbon
- 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.)
- Expired - Fee Related
Links
Images
Classifications
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/26—Removing halogen atoms or halogen-containing groups from the molecule
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- 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
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- 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
- C08K5/5425—Silicon-containing compounds containing oxygen containing at least one C=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
- C08K5/544—Silicon-containing compounds containing nitrogen
-
- 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
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08K5/57—Organo-tin compounds
-
- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- 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
- C09J143/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Adhesives based on derivatives of such polymers
- C09J143/04—Homopolymers or copolymers of monomers containing silicon
-
- 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
-
- 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
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/30—Chemical modification of a polymer leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/40—Chemical modification of a polymer taking place solely at one end or both ends of the polymer backbone, i.e. not in the side or lateral chains
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
(a)
アルコキシシラン官能化炭化水素化合物を形成するのに十分な時間、混合することを含む。
(a)
任意に(c)有機溶媒から作製されるアルコキシシラン官能化炭化水素化合物を調製し、アルコキシシラン官能化炭化水素化合物を形成するのに十分な時間、混合する方法を提供する。
以下に示すアクリレート末端ブチルアクリレート−エチルアクリレート−メトキシエチルアクリレートターポリマー:
(式中、IおよびRは、上で定義された通りであり、xは、92であり、yは、25であり、Zは、6であり、ターポリマーは、Mn約30,000の分子量を有する。)または
以下に示すアクリレート末端ブチルアクリレート−エチルアクリレート−アクリロニトリルターポリマー:
このような状況では、ポリマー上の所定の位置、たとえば、末端に所定の官能基を導入することが可能であるCRP技術を用いることがとくに有用であり得る。CRPは、重合速度が遅く、ラジカル−ラジカルカップリングによる停止の傾向が低いため、停止反応は容易には起こらず、そのため、狭い分子量分布(Mn/Mn=約1.1から1.5)を有するポリマーが得られ、モノマー/開始剤供給比を調節することによって、分子量を自由に制御することができるため、優位性がある。
<例1>
攪拌棒、磁気撹拌機、及び窒素導入口を備えた250mLの1口丸底フラスコに、制御ラジカル重合により調製した、MW27,000のアクリレート末端ブチルアクリレート/エチルアクリレート/アクリロニトリル(70/20/10)ターポリマー(27グラム、1モル)を添加し、次の反応で、ジアクリレートに変換した。ターポリマーに窒素下でアミノプロピルトリエトキシシラン(1.9g、8.8mmol)および酢酸エチル(100mL)を添加し、そして反応を、図2中の反応スキームに示される方針に沿って進行する。溶液を周囲温度で一晩撹拌し、その後、溶媒を減圧下で除去し、生成物を真空乾燥させた。収量=28.99g(定量)。
2オンスポリプロピレンスピードミキサーカップにMW30,000のターポリマー(15g)およびアミノプロピルトリエトキシシラン(0.9g)を添加した。カップはしっかりと蓋をし、スピードミキサに入れた。二つの成分を、3000rpmで3分間混合した。次いで、混合物を周囲温度で一晩熟成させた。プロトンNMR分析は、アクリレート二重結合上のプロトンに対応するピークがないため、反応が、完全であることを示した。収率=15.9g(定量)。
以下のアミノアルキルアルコキシシラン官能化炭化水素化合物を、RおよびR’が記載されているとおりの本明細書に記載の方法の方針に沿って調製した。
上記の例2の生成物(表中、「湿分硬化性ポリアクリレート」と称する)、MESAMOLL(商標)可塑剤、およびCAB−O−SIL TS530(商標)シリカの各々を、混合カップに加え、DAC150スピードミキサ内で混合した。その後、2つの架橋剤および触媒を加え、配合物の2回目の混合を行った(両方とも2750rpmで3分間)。サンプル番号1〜3をこのようにして形成した。また、例2の生成物の代わりに、KANEKA ORllOS(商標)ポリアクリレートを同量で用いて、同様にして対照サンプル(表1及び表2中のサンプル番号4)を形成した。様々な成分の表示および相対量を、下記表1(APTESキャップポリマーのための配向物)に示す。表2はサンプル番号5〜7を示し、APTMSまたはBESAはポリマーをキャップするために使用され、APTMSまたはBESAキャップポリマーは、APTESキャップポリマーと同じ量で使用した。
Claims (10)
- ポリアクリレートセグメントは、2つの置換可能なハロゲンを有する重合開始剤を用いて重合したものである、請求項1に記載の方法。
- 有機溶媒が、酢酸エチルである、請求項1に記載の方法。
- 混合を室温で行う、請求項1に記載の方法。
- 室温での混合を2から24時間の間行う、請求項5に記載の方法。
- 室温での混合を2から24時間の間行い、90%よりも多いアミノアルキルアルコキシシラン官能化炭化水素化合物の収率を達成する、請求項5に記載の方法。
- 構造1
Lは、1種または2種以上の(メタ)アクリレートモノマーおよび/またはアクリロニトリルモノマーを用いて作製されるポリアクリレートセグメントであり、Rは、アルキルであり、nは、2である。)の末端アクリロイル基が
以下の構造を有するアミノアルキルアルコキシシランによってアミノアルキルアルコキシシラン末端官能化されたアミノアルキルアルコキシシラン末端官能化炭化水素化合物。
(式中、R 1 およびR 2 は、炭素原子を1から4個有するアルキル基から選択され、R 3 は、アルキレンおよびアリーレン残基から選択され、R 4 は、水素及び炭素原子を1から4個有するアルキル基から選択され、xおよびyは、x+y=3を満たす整数であり、R 4 は、
自体であってもよい。) - (a)請求項8に記載のアミノアルキルアルコキシシラン末端官能化炭化水素化合物、および
(b)湿気硬化触媒
を含む、湿気硬化性組成物。 - 充填剤成分、強化剤成分、可塑剤成分および架橋剤成分の1種または複数をさらに含む、請求項9に記載の組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201361864924P | 2013-08-12 | 2013-08-12 | |
US61/864,924 | 2013-08-12 | ||
PCT/US2014/045754 WO2015023372A1 (en) | 2013-08-12 | 2014-07-08 | Alkoxysilane-functionalized polyacrylate compositions and methods of preparation thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016532754A JP2016532754A (ja) | 2016-10-20 |
JP6585045B2 true JP6585045B2 (ja) | 2019-10-02 |
Family
ID=52468570
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016534584A Expired - Fee Related JP6585045B2 (ja) | 2013-08-12 | 2014-07-08 | アルコキシシラン官能化ポリアクリレート組成物およびその調製方法。 |
Country Status (4)
Country | Link |
---|---|
US (2) | US20160152752A1 (ja) |
EP (1) | EP3033361A4 (ja) |
JP (1) | JP6585045B2 (ja) |
WO (1) | WO2015023372A1 (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA3059467A1 (en) | 2017-04-26 | 2018-11-01 | Henkel IP & Holding GmbH | Silane modified polymers with improved properties |
CA3061730A1 (en) | 2017-05-03 | 2018-11-08 | Henkel IP & Holding GmbH | Silane modified polymers with improved characteristics for adhesive compositions |
JP7067229B2 (ja) * | 2018-04-17 | 2022-05-16 | 信越化学工業株式会社 | 反応性ケイ素含有基を有するポリマーおよびその製造方法 |
CA3122282A1 (en) | 2018-12-21 | 2020-06-25 | Dow Silicones Corporation | Silicone-organic copolymer, sealants comprising same, and related methods |
US11760841B2 (en) | 2018-12-21 | 2023-09-19 | Dow Silicones Corporation | Silicone-polycarbonate copolymer, sealants comprising same, and related methods |
CN113045697B (zh) * | 2021-02-04 | 2021-10-12 | 东莞市德聚胶接技术有限公司 | 一种改性丙烯酸酯低聚物及一种uv、湿气双重固化压敏胶 |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60197733A (ja) * | 1984-03-21 | 1985-10-07 | Kanegafuchi Chem Ind Co Ltd | アミノシラン変性樹脂の製造法 |
US5648173A (en) * | 1996-01-25 | 1997-07-15 | Dow Corning Corporation | Room temperature, moisture-curable abrasion-resistant coating composition having enhancable weatherability |
IT1290179B1 (it) * | 1996-12-31 | 1998-10-19 | N P T New Polyurethane Technol | Polimero di poliaddizione di michael silano terminato |
JP2000072815A (ja) * | 1998-02-27 | 2000-03-07 | Kanegafuchi Chem Ind Co Ltd | 重合体及び硬化性組成物 |
US6964999B1 (en) * | 1998-02-27 | 2005-11-15 | Kaneka Corporation | Polymer and curable composition |
JP4176900B2 (ja) * | 1998-02-27 | 2008-11-05 | 株式会社カネカ | 硬化性組成物 |
JP4405619B2 (ja) * | 1998-07-23 | 2010-01-27 | 株式会社カネカ | 硬化性組成物 |
JP4215898B2 (ja) * | 1998-08-27 | 2009-01-28 | 株式会社カネカ | 粘着剤組成物 |
JP2000136211A (ja) * | 1998-08-27 | 2000-05-16 | Kanegafuchi Chem Ind Co Ltd | 水性エマルジョン |
AU2001237275A1 (en) * | 2000-01-11 | 2001-07-24 | Ciba Specialty Chemicals Holding Inc. | Comb polymers from atrp macromonomers |
US6287737B1 (en) * | 2000-05-30 | 2001-09-11 | Xerox Corporation | Photoconductive imaging members |
JP2002021790A (ja) * | 2000-07-06 | 2002-01-23 | Denso Corp | 遠心式送風機 |
US6631935B1 (en) * | 2000-08-04 | 2003-10-14 | Tru-Si Technologies, Inc. | Detection and handling of semiconductor wafer and wafer-like objects |
US8389630B2 (en) * | 2005-12-28 | 2013-03-05 | Kaneka Corporation | Curable composition |
US20080103261A1 (en) * | 2006-10-25 | 2008-05-01 | Bridgestone Corporation | Process for producing modified conjugated diene based polymer, modified conjugated diene based polymer produced by the process, rubber composition, and tire |
JP5569720B2 (ja) * | 2009-10-01 | 2014-08-13 | 東亞合成株式会社 | 湿気硬化性組成物の製造方法 |
EP2495286B1 (en) * | 2009-10-30 | 2016-03-23 | Kaneka Corporation | Curable composition |
US8729179B1 (en) * | 2012-08-20 | 2014-05-20 | Henkel US IP LLC | Moisture curable polyacrylates |
-
2014
- 2014-07-08 WO PCT/US2014/045754 patent/WO2015023372A1/en active Application Filing
- 2014-07-08 JP JP2016534584A patent/JP6585045B2/ja not_active Expired - Fee Related
- 2014-07-08 EP EP14835793.2A patent/EP3033361A4/en not_active Withdrawn
-
2016
- 2016-02-08 US US15/017,692 patent/US20160152752A1/en not_active Abandoned
-
2018
- 2018-11-07 US US16/182,768 patent/US20190071528A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
US20190071528A1 (en) | 2019-03-07 |
US20160152752A1 (en) | 2016-06-02 |
EP3033361A1 (en) | 2016-06-22 |
WO2015023372A1 (en) | 2015-02-19 |
JP2016532754A (ja) | 2016-10-20 |
EP3033361A4 (en) | 2017-05-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6585045B2 (ja) | アルコキシシラン官能化ポリアクリレート組成物およびその調製方法。 | |
JP2022075628A (ja) | 硬化性組成物の製造方法 | |
CN107698766B (zh) | 支链聚有机硅氧烷及相关的可固化组合物、方法、用途和器件 | |
JP6426628B2 (ja) | 官能基密集型ポリオルガノシロキサン及びシリコーン反応性希釈剤を含む硬化性シリコーン組成物 | |
KR102206708B1 (ko) | 안정한 열 라디칼 경화성 실리콘 접착제 조성물 | |
JP6323838B2 (ja) | アルコキシ官能性オルガノポリシロキサン樹脂及びポリマー並びにそれを形成する関連する方法 | |
JP6930917B2 (ja) | 硬化性シロキサン組成物 | |
JP6284938B2 (ja) | 湿気硬化性ポリアクリレート | |
US20160009865A1 (en) | Clustered Functional Polyorganosiloxanes, Processes For Forming Same And Methods For Their Use | |
US10287368B2 (en) | Alkoxysilane-functionalized hydrocarbon compounds, intermediates thereof and methods of preparation thereof | |
JPH0649711B2 (ja) | ビスマレイミド化合物及びこれを用いたフリーラジカル硬化性配合組成物 | |
JP6477473B2 (ja) | 湿気硬化性組成物 | |
JPH04185687A (ja) | 接着剤組成物 | |
JPH03294320A (ja) | 貯蔵安定性の優れた硬化性組成物 | |
JP2016132763A (ja) | 硬化性樹脂組成物 | |
JP2003128907A (ja) | 一液湿気硬化型可撓性樹脂組成物 | |
JPH0493364A (ja) | 貯蔵安定性の優れた硬化性組成物 | |
WO2017191455A1 (en) | Adhesion promoters | |
JP2018100322A (ja) | 反応性ホットメルト接着剤組成物 | |
JP2017149868A (ja) | オルガノポリシロキサン及びその製造方法 | |
JP2015048426A (ja) | 硬化性樹脂組成物 | |
JP2010202547A (ja) | シラン化合物、並びに該シラン化合物から誘導される硬化性シリコーン系樹脂、硬化性シリコーン系樹脂組成物、及び、室温硬化性接着剤組成物 | |
JP2010018661A (ja) | 硬化性樹脂組成物及びその製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20170707 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20180423 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20180425 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180515 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20180815 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20181015 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20181112 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190416 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190709 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20190806 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20190904 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6585045 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
LAPS | Cancellation because of no payment of annual fees |