JP4967656B2 - 光カチオン重合性組成物及びそれを用いたオプトエレクトロニクス部品 - Google Patents
光カチオン重合性組成物及びそれを用いたオプトエレクトロニクス部品 Download PDFInfo
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- JP4967656B2 JP4967656B2 JP2006514693A JP2006514693A JP4967656B2 JP 4967656 B2 JP4967656 B2 JP 4967656B2 JP 2006514693 A JP2006514693 A JP 2006514693A JP 2006514693 A JP2006514693 A JP 2006514693A JP 4967656 B2 JP4967656 B2 JP 4967656B2
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- WQYCAPDZCNPCMA-UHFFFAOYSA-N cyclohexyl-(4-propan-2-ylphenyl)methanone Chemical compound C1=CC(C(C)C)=CC=C1C(=O)C1CCCCC1 WQYCAPDZCNPCMA-UHFFFAOYSA-N 0.000 description 1
- 238000004512 die casting Methods 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
- C08G59/68—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 characterised by the catalysts used
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- 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
- C08K5/02—Halogenated hydrocarbons
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
-
- 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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/22—Expanded, porous or hollow particles
- C08K7/24—Expanded, porous or hollow particles inorganic
- C08K7/28—Glass
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
(A)水添ビスフェノール型エポキシ樹脂を5重量%以上含むカチオン重合性化合物100重量部と、
(B)下記一般式(1)に示す構造のヨードニウム塩の1種以上0.01〜10重量部と、
(C)下記一般式(2)、(3)、(4)に示すいずれかの構造を有するベンゾイル化合物の1種以上0.01〜10重量部と、
(D)繊維長1〜500μm、繊維径0.5〜100μmのガラスファイバー10〜90重量部の、上記(A)〜(D)を主成分とする光カチオン重合性組成物により、耐久性、接着性、特に精密固定性に優れ、また硬化後の寸法安定性に対しても極めて位置ずれの少ない接着剤が得られることを見い出し、更には硬化速度向上の設計が可能であることからこの発明を完成するに至った。
また、下記構造で示す以外の水添(水素化)ビスフェノール型エポキシ樹脂を用いることも当然可能である。また水添化されたものは耐候性、耐変色性が向上する為、好ましい。
本発明における光カチオン重合性化合物のうち、上記構造式で示すような水添ビスフェノール型エポキシ樹脂を除いた化合物としては、下記に各化合物を例示することができる。また、これらの各化合物は1種または2種以上を混合して使用することができる。
また、本発明に用いるベンゾイル化合物(C)として、下記一般式(2)、(3)、(4)で表される有機化合物を挙げることができる。
また、このガラスファイバーは、カチオン重合性化合物100重量部中に、10〜90重量部、更に好ましくは20〜70重量部の割合で添加することができる。10重量部未満では線膨張係数が増大し、精密性を欠く、また90重量部を超えると接着性が低下する傾向にある。
以下実施例及び比較例により更に具体的にこの発明を説明するが、この発明はこれらの実施例に限定されるものではない。
調合容器の周囲を遮光し、光カチオン重合性化合物、光カチオン重合性開始剤、ベンゾイル系化合物、ポリオール化合物を表1及び2に示すとおりの所定量を配合し、50℃に加温しながら混合攪拌する事により均一な調合液を得た。なお、表中の配合量はすべて重量部である。続いて前記調合液に、ファイバー系、及び球状系のガラス系充填剤を添加してさらに混合撹拌した後、減圧脱泡して目的の光カチオン重合性組成物を調合した(実施例1〜11、比較例1〜10)。
・接着性試験について
亜鉛ダイキャスト(JIS H 5301)の試験片に調合した接着剤を塗布し、ガラス試験片を貼り合わせて、ガラス側から紫外線を10秒照射(積算光量約3000mJ/cm2)し、試験片を接着硬化後、約2時間放置し、評価用試験片とした。この試験片をJIS K 6850(スリーボンド規格 3TS−301−13)に基づいてせん断接着強さを測定した。
・塗布性
調合した接着剤をシリンジに充填し、サイズ20Gのノズルにてディスペンスを行う。この際の流れ性を目視で確認し、塗布性を判断した。
また、流れ性良い:○ 流れ性悪い:× で示した。
・光硬化性(表面)
調合した接着剤をガラス板上に塗布し、紫外線を10秒照射(積算光量約3000mJ/cm2)後、直ちに表面のタックを指触で確認した。
また、タック無く潤滑性があり:◎ タック無し:○ タック有り:× で示した。
・光硬化性(深部mm)
調合した接着剤を遮光されたプラスチック筒(内径φ5mm、t10mm)中に充填し、紫外線を10秒照射(積算光量約3000mJ/cm2)後、直ちに深部硬化距離を測定した。
また、評価としては、硬化深度をmm単位で測定し、小数点以下四捨五入して示した。
・寸法安定性試験について
光硬化物の線膨張率を測定し、α1(Tg前)の値をJIS K 6850に準じて測定した。(スリーボンド規格 3TS−501−05)
上記各試験の結果を表1(実施例)及び表2(比較例)にまとめて示した。
<エポキシ樹脂>
水添Bis−A(n=0)とは、水素化エポキシ樹脂で前記構造式で示される繰り返し単位が0〜3(主成分はn=0)の化合物を用いた。
水添Bis−A(n=0.5)とは、水素化エポキシ樹脂で前記構造式で示される繰り返し単位が0〜8(主成分はn=0)の化合物を用いた。
「EP−830」:ビスフェノールF型エポキシ樹脂
・・・ ジャパンエポキシレジン(株)社製
<カチオン重合性光開始剤>
「t−BuDBI」:ターシャリーブチルジフェニルヨードニウムヘキサフルオロフォスフェート
・・・ ダウ・ケミカル社製
「UVI−6992」:トリアリルスルホニウムヘキサフルオロフォスフェート
・・・ ダウ・ケミカル社製
「PI−2074」:トリルクミルヨードニウムテトラキス(ペンタフルオロフェニル)ボレート
・・・ ローディアジャパン社製
「ダロキュア1173」:2−ヒドロキシ−2−メチル−1−フェニル−プロパン−1−オン
・・・ チバスペシャリティーケミカルズ社製
「イルガキュア184」:1−ヒドロキシ−シクロヘキシル−フェニル−ケトン
・・・ チバスペシャリティーケミカルズ社製
「PFE−301S」:ミルドファイバー
・・・ 日東紡社製
「CS3PE−332S」:チョップドストランド
・・・ 日東紡社製
「クリスタライト A2」:ガラスビーズ
・・・ 株式会社龍森製
Claims (6)
- (A)水添ビスフェノール型エポキシ樹脂を5重量%以上含むエポキシ樹脂からなるカチオン重合性化合物20〜80重量部と;
(B)下記一般式(1)に示す構造のヨードニウム塩の1種以上0.01〜10重量部と、
(C)下記一般式(2)、(3)、又は(4)に示すいずれかの構造を有するベンゾイル化合物の1種以上を0.01〜10重量部と、
(D)繊維長1〜500μm、繊維径0.5〜100μmのガラスファイバーを20〜80重量部の、上記(A)〜(D)を主成分とする光カチオン重合性組成物。 - 前記ガラスファイバー(D)が、繊維長5〜100μm、繊維径1〜20μmである、請求項1に記載の光カチオン重合性組成物。
- 前記ガラスファイバー(D)が、ビニル基、エポキシ基、アミノ基、(メタ)アクリル基、メルカプト基、メトキシ基、又はエトキシ基を有するシラン化合物で表面処理されていている、請求項1に記載の光カチオン重合性組成物。
- 前記(A)カチオン重合性化合物100重量部に対して、分子中に少なくとも2個の水酸基を有する化合物を、さらに0.5〜50重量部含有する、請求項1に記載の光カチオン重合性組成物。
- 前記請求項1〜5のいずれか1項に記載の光カチオン重合性組成物を用いて成形、又は接着することで製造されたオプトエレクトロニクス部品。
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JP2007284500A (ja) * | 2006-04-13 | 2007-11-01 | Sekisui Chem Co Ltd | 光学部品用接着剤 |
JP5168860B2 (ja) * | 2006-09-14 | 2013-03-27 | 株式会社スリーボンド | 光重合性組成物 |
JP5329299B2 (ja) * | 2009-05-13 | 2013-10-30 | 日東電工株式会社 | 光学レンズ |
KR101225483B1 (ko) * | 2010-06-15 | 2013-01-23 | 연세대학교 산학협력단 | 난접착 금속용 코팅 조성물 및 이의 제조방법 |
DE102011056295B4 (de) | 2011-12-12 | 2022-02-17 | OSRAM Opto Semiconductors Gesellschaft mit beschränkter Haftung | Epoxidharzsystem, Verwendung des Epoxidharzsystems, alterungsbeständiger Epoxidharzformstoff und Bauelement mit dem Epoxidharzformstoff |
KR101355855B1 (ko) * | 2011-12-19 | 2014-01-29 | 제일모직주식회사 | 이방성 도전 필름 |
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CN103031066B (zh) * | 2012-12-30 | 2014-09-03 | 南通万德科技有限公司 | 光固化转印材料 |
JP6331013B2 (ja) * | 2014-05-21 | 2018-05-30 | 株式会社スリーボンド | カチオン硬化性樹脂組成物 |
CN110894411B (zh) * | 2019-12-16 | 2021-09-21 | 苏州瑞力博新材科技有限公司 | 一种用于叠瓦太阳能组件的环氧导电胶及制备方法 |
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US5789039A (en) * | 1994-09-06 | 1998-08-04 | Herberts Powder Coatings, Inc. | Radiation curing of powder coatings on heat sensitive substrates: chemical compositions and processes for obtaining coated workpieces |
US5877229A (en) * | 1995-07-26 | 1999-03-02 | Lockheed Martin Energy Systems, Inc. | High energy electron beam curing of epoxy resin systems incorporating cationic photoinitiators |
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KR20070041689A (ko) | 2007-04-19 |
JPWO2005123803A1 (ja) | 2008-04-10 |
WO2005123803A1 (ja) | 2005-12-29 |
EP1760102A1 (en) | 2007-03-07 |
KR101186452B1 (ko) | 2012-09-27 |
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