JP2010202863A - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
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- JP2010202863A JP2010202863A JP2010022138A JP2010022138A JP2010202863A JP 2010202863 A JP2010202863 A JP 2010202863A JP 2010022138 A JP2010022138 A JP 2010022138A JP 2010022138 A JP2010022138 A JP 2010022138A JP 2010202863 A JP2010202863 A JP 2010202863A
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- 239000011347 resin Substances 0.000 claims abstract description 73
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
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- -1 amine compound Chemical class 0.000 claims description 103
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 238000010526 radical polymerization reaction Methods 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
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- QJOOZNCPHALTKK-UHFFFAOYSA-N trimethoxysilylmethanethiol Chemical compound CO[Si](CS)(OC)OC QJOOZNCPHALTKK-UHFFFAOYSA-N 0.000 description 8
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- 125000005370 alkoxysilyl group Chemical group 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- LWMFAFLIWMPZSX-UHFFFAOYSA-N bis[2-(4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene Chemical compound N=1CCNC=1C(C)(C)N=NC(C)(C)C1=NCCN1 LWMFAFLIWMPZSX-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 239000006096 absorbing agent Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 5
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- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 4
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- CKSAKVMRQYOFBC-UHFFFAOYSA-N 2-cyanopropan-2-yliminourea Chemical compound N#CC(C)(C)N=NC(N)=O CKSAKVMRQYOFBC-UHFFFAOYSA-N 0.000 description 4
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- CDVLARZRMIEPMF-UHFFFAOYSA-N [methoxy(dimethyl)silyl]methyl prop-2-enoate Chemical compound CO[Si](C)(C)COC(=O)C=C CDVLARZRMIEPMF-UHFFFAOYSA-N 0.000 description 4
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- 150000004820 halides Chemical class 0.000 description 3
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- 150000002432 hydroperoxides Chemical class 0.000 description 3
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Abstract
Description
本発明の硬化性組成物は、(A)下記一般式(1)で示される化合物及び下記一般式(2)で示される化合物を反応させて得られるビニル系樹脂、及び(B)硬化触媒を含むことを特徴とする。
本発明の硬化性組成物において、前記(A)ビニル系樹脂100質量部に対して、前記(B)硬化触媒を0.000001〜10質量部配合することが好適である。
前記式(2)及び(4)において、R4は、水素原子、ハロゲン原子又は炭素数1〜3のアルキル基であり、R5は、水素原子、アルカリ金属原子、炭素数1〜24の炭化水素含有基である。
フリーラジカル重合法を用いる場合は、連鎖移動剤、開始剤を用いて0℃〜200℃で反応させることが好ましい。より好ましくは25℃〜150℃範囲内に設定することが特に好ましい。重合反応温度を上記範囲内に設定することにより、反応を暴走させることなく安定に進行させることができる。使用する重合性不飽和化合物の不飽和基の活性にもよるが、比較的重合性の高いアクリル酸エステル系の重合性不飽和化合物を用いた場合でも、反応温度を0℃未満とした場合、活性が低くなり、充分な重合率を達成するために必要な時間が長くなり、効率が悪い。さらに、スチレン型不飽和化合物のように重合活性が低い化合物を用いた場合でも、25℃以上の条件であれば、充分な重合率を達成することができる。フリーラジカル重合法を用いる場合において、反応時間は、重合率、分子量等を考慮して適宜設定することができるが、例えば上記のような条件では反応時間は、通常は1〜144時間、好ましくは2〜8時間の範囲内に設定することが好ましい。
付加−開裂移動反応重合法を用いる場合は、連鎖移動剤、開始剤を用いて0℃〜200℃で反応させることが好ましい。より好ましくは25℃〜150℃範囲内に設定することが特に好ましい。重合反応温度を上記範囲内に設定することにより、反応を暴走させることなく安定に進行させることができる。使用する重合性不飽和化合物の不飽和基の活性にもよるが、比較的重合性の高いアクリル酸エステル系の重合性不飽和化合物を用いた場合でも、反応温度を0℃未満とした場合、活性が低くなり、充分な重合率を達成するために必要な時間が長くなり、効率が悪い。さらに、スチレン型不飽和化合物のように重合活性が低い化合物を用いた場合でも、25℃以上の条件であれば、充分な重合率を達成することができる。付加−開裂移動反応重合法を用いる場合において、反応時間は、重合率、分子量等を考慮して適宜設定することができるが、例えば上記のような条件では反応時間は、通常は30分〜144時間、好ましくは1〜24時間の範囲内に設定することが好ましい。
金属触媒としてメタロセン化合物を用い、さらに分子中に少なくとも1つの反応性シリル基を有するチオール化合物を用いて0℃〜150℃で反応させることが好ましい。より好ましくは25℃〜120℃範囲内に設定することが特に好ましい。重合反応温度を上記範囲内に設定することにより、反応を暴走させることなく安定に進行させることができる。使用する重合性不飽和化合物の不飽和基の活性にもよるが、比較的重合性の高いアクリル酸エステル系の重合性不飽和化合物を用いた場合でも、反応温度を0℃未満とした場合、活性が低くなり、充分な重合率を達成するために必要な時間が長くなり、効率が悪い。さらに、スチレン型不飽和化合物のように重合活性が低い化合物を用いた場合でも、25℃以上の条件であれば、充分な重合率を達成することができる。該重合法を用いる場合において、反応時間は、重合率、分子量等を考慮して適宜設定することができるが、例えば上記のような条件では反応時間は、通常は1〜12時間、好ましくは2〜8時間の範囲内に設定することが好ましい。
遷移金属錯体を用いたラジカル重合法を用いる場合は、遷移金属錯体、有機ハロゲン化物及び/または配位子を用いて0℃〜200℃で反応させることが好ましい。より好ましくは25℃〜150℃範囲内に設定することが特に好ましい。重合反応温度を上記範囲内に設定することにより、反応を暴走させることなく安定に進行させることができる。使用する重合性不飽和化合物の不飽和基の活性にもよるが、比較的重合性の高いアクリル酸エステル系の重合性不飽和化合物を用いた場合でも、反応温度を0℃未満とした場合、活性が低くなり、充分な重合率を達成するために必要な時間が長くなり、効率が悪い。さらに、スチレン型不飽和化合物のように重合活性が低い化合物を用いた場合でも、25℃以上の条件であれば、充分な重合率を達成することができる。付加−開裂移動反応重合法を用いる場合において、反応時間は、重合率、分子量等を考慮して適宜設定することができるが、例えば上記のような条件では反応時間は、通常は30分〜144時間、好ましくは1〜24時間の範囲内に設定することが好ましい。
また、2価の塩化ルテニウムのトリストリフェニルホスフィン錯体(RuCl2(PPh3)3)も触媒として好適である。ルテニウム化合物を触媒として用いる場合は、活性化剤としてアルミニウムアルコキシド類が添加される。更に、2価の鉄のビストリフェニルホスフィン錯体(FeCl2(PPh3)2)、2価のニッケルのビストリフェニルホスフィン錯体(NiCl2(PPh3)2)、及び2価のニッケルのビストリブチルホスフィン錯体(NiBr2(PBu3)2)も触媒として好適である。
具体的に例示するならば、C6H5−CH2X、C6H5−C(H)(X)CH3、C6H5−C(X)(CH3)2、XCH2−C6H5−CH2X、XC(H)(CH3)−C6H5−C(H)(CH3)X(ただし、上の化学式中、C6H5はフェニル基、Xは塩素、臭素、またはヨウ素)、R6−C(H)(X)−CO2R7、R6−C(CH3)(X)−CO2R7、R6−C(H)(X)−C(O)R7、R6−C(CH3)(X)−C(O)R7、(式中、R6、R7は水素原子または炭素数1〜20のアルキル基、アリール基、またはアラルキル基、Xは塩素、臭素、またはヨウ素)、R6−C6H4−SO2X(上記の各式において、R6は水素原子または炭素数1〜20のアルキル基、アリール基、またはアラルキル基、Xは塩素、臭素、またはヨウ素)等が挙げられる。
前記(A)ビニル系樹脂は、前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位を含むものであり、前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位とが構造単位比として0.001:1〜5:1が好ましく、0.005:1〜0.5:1がより好ましい。
前記(A)ビニル系樹脂に含まれる一般式(3)で示される構造単位の個数は特に限定はないが、1分子中に平均して0.2個〜5個含まれることが好ましく、0.5個〜3.0個含まれることがより好ましい。一般式(4)で示される構造単位は、1分子中に平均して10個〜2000個含まれることが好ましく、15個〜1000個含まれることがより好ましい。
具体的には、第一級アミノ基を有する化合物として、第1級アミンが好適である。該第1級アミノとしては、例えば、メチルアミン、エチルアミン、プロピルアミン、イソプロピルアミン、ブチルアミン、イソブチルアミン、2−ブチルアミン、1,2−ジメチルプロピルアミン、ヘキシルアミン、へプチルアミン、2−エチルヘキシルアミン、ノニルアミン、デシルアミン、アミルアミン、オクチルアミン、3−ペンチルアミン、イソアミルアミン、2−オクチルアミン、3−メトキシプロピルアミン、3−プロポキシプロピルアミン、3−ブトキシプロピルアミン、3−イソブトキシプロピルアミン、ラウリルアミン、ペンタデシルアミン、ロジンアミン、テトラデシルアミン、ペンタデシルアミン、セチルアミン、ステアリルアミン、シクロヘキシルアミン、トリメチルシクロヘキシルアミン、ベンジルアミン、アニリン、3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリエトキシシラン、3−アミノプロピルメチルジメトキシシラン、3−アミノプロピルメチルジエトキシシラン、アミノメチルトリメトキシシラン、アミノメチルアミノメチルトリエトキシシラン、アミノメチルメチルジメトキシシラン、アミノメチルメチルジエトキシシラン、アミノメチルジメチルメトキシシラン、アミノメチルジメチルエトキシシラン等のモノアミン;エチレンジアミン、1,3−ジアミノプロパン、1,2−ジアミノプロパン、1,4−ジアミノブタン、ヘキサメチレンジアミン、1,7−ジアミノへプタン、トリメチルヘキサメチレンジアミン、1,8−ジアミノオクタン、1,9−ジアミノノナン、1,10−ジアミノデカン、1,11−ジアミノウンデカン、1,12−ジアミノドデカン、1,13−ジアミノトリデカン、1,14−ジアミノテトラデカン、1,15−ジアミノペンタデカン、1,16−ジアミノヘキサデカン、1,17−ジアミノヘプタデカン、1,18−ジアミノオクタデカン、1,19−ジアミノノナデカン、1,20−ジアミノエイコサン、1,21−ジアミノヘンティコサン、1,22−ジアミノドコサン、1,23−ジアミノトリコサン、1,24−ジアミノテトラコサン、イソホロンジアミン、ジアミノジシクロへキシルメタン、3,9−ビス(3−アミノプロピル)−2,4,8,10−テトラオキサスピロ(5,5)ウンデカン、キシレンジアミン、フェニレンジアミン、ジアミノジフェニルメタン、ジアミノジエチルフェニルメタン、ポリオキシエチレンジアミン、ポリオキシプロピレンジアミン等のジアミン;トリ(メチルアミノ)へキサン等のポリアミンが挙げられる。
1)数平均分子量の測定
ゲルパーミエーションクロマトグラフィー(GPC)により下記条件で測定した。本発明において、該測定条件でGPCにより測定し、標準ポリエチレングリコールで換算した最大頻度の分子量を数平均分子量と称する。
THF溶媒測定装置
・分析装置:Alliance(Waters社製)、2410型示差屈折検出器(Waters社製)、996型多波長検出器(Waters社製)、Milleniamデータ処理装置(Waters社製)
・カラム:Plgel GUARD+5μmMixed−C×3本(50×7.5mm,300×7.5mm:PolymerLab社製)
・流速:1mL/分
・換算したポリマー:ポリエチレングリコール
・測定温度:40℃
フラスコ内の硬化性組成物を室温にて3週間放置し、フラスコを傾けて目視にてその粘度を確認した。
JIS A 1439 4.19により指触乾燥時間(TFT)を測定し、硬化性を評価した。60秒以内に皮膜形成すると○(良好)、60〜600秒以内の場合は△(やや良好)、600秒を超えた場合×(不良)と評価した。
4−1)接着性
被着材の上に0.2gの硬化性組成物を均一に塗布し、25mm×25mmの面積で直ちに貼り合わせた。貼り合わせ後、23℃相対湿度50%の雰囲気下で7日間、目玉クリップ小により圧締した直後にJIS K 6850 剛性被着材の引張りせん断接着強さ試験方法に準じて測定した。被着材としては、ポリカーボネイト及びAlを使用した。
ラワン合板(厚さ5mm、幅25mm、長さ100mm)の上に0.2gの硬化性組成物を均一に塗布し、25mm×25mmの面積で直ちに張り合わせた。貼り合わせ後、23℃相対湿度50%の雰囲気下で所定時間、目玉クリップ小により圧締した直後にJIS K 6850 剛性被着材の引張りせん断接着試験方法に準じて測定した。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表1に示した如く、n−ブチルアクリレート50.0質量部、アクリロキシメチルトリメトキシシラン2.06質量部、さらにメルカプトメチルトリメトキシシラン3.37質量部加え、80℃に加熱した。THF5mLに溶かしたAIBN2.48質量部を3時間かけて滴下し、さらに6時間80℃反応させ、ビニル系樹脂A1を得た。得られたビニル系樹脂A1の数平均分子量は5000であり、且つMw/Mn=1.6であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.0256:1であった。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表1に示した如く、n−ブチルアクリレート100.0質量部、メタクリロキシメチルトリメトキシシラン2.20質量部、さらにメルカプトプロピルトリメトキシシラン3.93質量部加え、80℃に加熱した。THF5mLに溶かしたBPO2.42質量部を3時間かけて滴下し、さらに6時間80℃反応させ、ビニル系樹脂A2を得た。得られたビニル系樹脂A2の数平均分子量は10000であり、且つMw/Mn=1.8であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.0128:1であった。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表1に示した如く、n−ブチルアクリレート40質量部、メチルメタクリレート7.81質量部、アクリロキシメチルトリメトキシシラン2.06質量部、さらにメルカプトプロピルトリメトキシシラン3.93質量部加え、80℃に加熱した。THF5mLに溶かしたBPO2.42質量部を3時間かけて滴下し、さらに6時間80℃反応させ、ビニル系樹脂A3を得た。得られたビニル系樹脂A3の数平均分子量は5000であり、且つMw/Mn=1.6であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.0256:1であった。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表1に示した如く、n−ブチルアクリレート25質量部、ステアリルメタクリレート65.92質量部、アクリロキシメチルトリメトキシシラン2.06質量部、さらにメルカプトメチルトリメトキシシラン3.37質量部加え、80℃に加熱した。THF5mLに溶かしたAIBN2.48質量部を3時間かけて滴下し、さらに6時間80℃反応させ、ビニル系樹脂A4を得た。得られたビニル系樹脂A4の数平均分子量は5000であり、かつMw/Mn=1.6であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.0256:1であった。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表1に示した如く、n−ブチルアクリレート25質量部、2−エチルヘキシルメタクリレート38.62質量部、アクリロキシメチルトリメトキシシラン2.06質量部、さらにメルカプトプロピルトリメトキシシラン3.37質量部加え、80℃に加熱した。THF5mLに溶かしたAIBN2.48質量部を3時間かけて滴下し、さらに6時間80℃反応させ、ビニル系樹脂A5を得た。得られたビニル系樹脂A5の数平均分子量は5000であり、かつMw/Mn=1.6であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.0256:1であった。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表1に示した如く、n−ブチルアクリレート50.0質量部、アクリロキシメチルトリメトキシシラン2.06質量部加え、80℃に加熱した。THF20mLに溶かしたADVN10質量部を3時間かけて滴下し、さらに6時間80℃反応させ、ビニル系樹脂A6を得た。得られたビニル系樹脂A6の数平均分子量は5000であり、かつMw/Mn=3.0であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.0256:1であった。
撹拌装置、窒素ガス導入管、温度計および還流冷却管を備えたフラスコに、表2に示した如く、キシレン43質量部、メチルメタクリレート20質量部、2−エチルヘキシルメタクリレート80質量部、アクリロキシメチルトリメトキシシラン20質量部、及び金属触媒としてジルコノセンジクロライド0.1質量部を仕込みフラスコ内に窒素ガスを導入しながらフラスコの内容物を80℃に加熱した。ついで、充分に窒素ガス置換したメルカプトメチルトリメトキシシラン20質量部を撹拌下にフラスコ内に一気に添加した。メルカプトメチルトリメトキシシラン20質量部を添加後、撹拌中のフラスコ内の内容物の温度が80℃に維持できるように、加熱及び冷却を4時間行った。さらに、充分に窒素ガス置換したメルカプトメチルトリメトキシシラン20質量部を撹拌下に5分かけてフラスコ内に追加添加した。メルカプトメチルトリメトキシシラン20質量部全量を追加添加後、撹拌中のフラスコ内の内容物の温度が90℃に維持できるように、さらに冷却及び加温を行いながら、反応を4時間行った。合計で8時間5分間の反応後、反応物の温度を室温に戻し、反応物にベンゾキノン溶液(95%THF溶液)を20質量部添加して重合を停止し、ビニル系樹脂A7を得た。得られたビニル系樹脂A7の数平均分子量は5000であり、かつMw/Mn=1.6であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.1607:1であった。
撹拌装置、窒素ガス導入管、温度計および還流冷却管を備えたフラスコに、表2に示した如く、キシレン43質量部、メチルメタクリレート20質量部、ステアリルメタクリレート80質量部、メタクリロキシメチルトリメトキシシラン20質量部、及び金属触媒としてルテノセンジクロライド0.1質量部を仕込みフラスコ内に窒素ガスを導入しながらフラスコの内容物を80℃に加熱した。ついで、充分に窒素ガス置換した3−メルカプトプロピルトリメトキシシラン20質量部を撹拌下にフラスコ内に一気に添加した。3−メルカプトプロピルトリメトキシシラン20質量部を添加後、撹拌中のフラスコ内の内容物の温度が80℃に維持できるように、加熱及び冷却を4時間行った。さらに、充分に窒素ガス置換した3−メルカプトプロピルトリメトキシシラン20質量部を撹拌下に5分かけてフラスコ内に追加添加した。3−メルカプトプロピルトリメトキシシラン20質量部全量を追加添加後、撹拌中のフラスコ内の内容物の温度が90℃に維持できるように、さらに冷却及び加温を行いながら、反応を4時間行った。合計で8時間5分間の反応後、反応物の温度を室温に戻し、反応物にベンゾキノン溶液(95%THF溶液)を20質量部添加して重合を停止し、ビニル系樹脂A8を得た。得られたビニル系樹脂A8の数平均分子量は5000であり、かつMw/Mn=1.6であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.2082:1であった。
撹拌装置、窒素ガス導入管、温度計および還流冷却管を備えたフラスコに、表2に示した如く、n−ブチルアクリレート100質量部、アクリロキシメチルトリメトキシシラン5.95質量部、合成した1−フェニルエチルジチオベンゾエ−ト4質量部、AIBN1.27質量部を仕込みフラスコ内に窒素ガスを導入しながらフラスコの内容物を80℃に加熱した。撹拌中のフラスコ内の内容物の温度が80℃に維持できるように、加熱及び冷却を8時間行った。反応後、反応物の温度を室温に戻し、ビニル系樹脂A9を得た。得られたビニル系樹脂A9の数平均分子量は7000であり、かつMw/Mn=1.1であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.0369:1であった。
撹拌装置、窒素ガス導入管、温度計および還流冷却管を備えたフラスコに、表2に示した如く、トルエン43質量部、2−エチルヘキシルメタクリレート100質量部、メタクリロキシメチルトリメトキシシラン5.95質量部、メチル2−ブロモプロピオネート4質量部及び金属触媒としてジルコノセンジクロライド1質量部、トリイソプロポキシアルミニウムを1質量部仕込みフラスコ内に窒素ガスを導入しながらフラスコの内容物を80℃に加熱した。8時間の反応後、反応物の温度を室温に戻し、反応物にベンゾキノン溶液(95%THF溶液)を20質量部添加して重合を停止し、ビニル系樹脂A10を得た。得られたビニル系樹脂A10の数平均分子量は6400であり、かつMw/Mn=1.6であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.0535:1であった。
撹拌装置、窒素ガス導入管、温度計および還流冷却管を備えたフラスコに、表2に示した如く、プロピレンカーボネートを10質量部、n−ブチルアクリレート100質量部、アクリロキシメチルトリメトキシシラン6質量部、メチル2−ブロモプロピオネート5.21質量部及び遷移金属触媒としてCuBr4.46質量部、配位子としてN,N,N’,N’’,N’’―ペンタメチレンジエチレントリアミン2.76質量部仕込みフラスコ内に窒素ガスを導入しながらフラスコの内容物を80℃に加熱した。12時間の反応後、反応物の温度を室温に戻し、反応物にベンゾキノン溶液(95%THF溶液)を20質量部添加して重合を停止し、脱水メタノール(東京化成工業(株)製)にて反応物を沈殿精製し、ビニル系樹脂A11を得た。得られたビニル系樹脂A11の数平均分子量は6500であり、かつMw/Mn=1.1であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.0372:1であった。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表3に示した如く、2−エチルヘキシルメタクリレート72.0質量部、アクリロキシメチルトリメトキシシラン32.1質量部、さらにメルカプトプロピルトリメトキシシラン10.1質量部加え、80℃に加熱した。THF5mLに溶かしたAIBN5.0質量部を3時間かけて滴下し、さらに6時間80℃反応させ、ビニル系樹脂A12を得た。得られたビニル系樹脂A12の数平均分子量は2200であり、且つMw/Mn=1.8であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.4286:1であった。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表3に示した如く、酢酸エチル100質量部を加え80℃に加熱した。別の容器にメチルメタクリレート20.0質量部、ラウリルメタクリレート203.2質量部、メタクリロキシメチルトリメトキシシラン22.0質量部、さらにメルカプトプロピルメチルジキシシラン9.82質量部、AIBN5.0質量部を加え、滴下ロートにて3時間かけて滴下し、さらに6時間80℃反応させ、80℃にて減圧下により酢酸エチルや未反応成分を除去しビニル系樹脂A13を得た。得られたビニル系樹脂A13の数平均分子量は5100であり、且つMw/Mn=1.6であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.1:1であった。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表3に示した如く、酢酸エチル100質量部加え80℃に加熱した。別の容器にメチルメタクリレート10.0質量部、ラウリルメタクリレート203.2質量部、ステアリルメタクリレート16.9質量部、N,N―ジメチルアクリルアミド4.95質量部、アクリロキシメチルジメチルメトキシシラン26.14質量部、さらにラウリルメルカプタン10.12質量部、AIBN4.11質量部を加え、滴下ロートにて3時間かけて滴下し、さらに6時間80℃反応させ、80℃にて減圧下により酢酸エチルや未反応成分を除去しビニル系樹脂A14を得た。得られたビニル系樹脂A14の数平均分子量は5100であり、且つMw/Mn=1.6であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.133:1であった。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表3に示した如く、トルエン100質量部加え100℃に加熱した。別の容器にラウリルメタクリレート203.2質量部、ステアリルメタクリレート33.8質量部、N,N―ジメチルアクリルアミド4.95質量部、N,N−ジメチルアミノエチルアクリレート7.16質量部、アクリロキシメチルメチルジメトキシシラン28.54質量部、さらにメルカプトプロピルトリメトキシシラン9.82質量部、AIBN4.11質量部を加え、滴下ロートにて3時間かけて滴下し、さらに2時間100℃反応させ、100℃にて減圧下によりトルエンや未反応成分を除去しビニル系樹脂A15を得た。得られたビニル系樹脂A15の数平均分子量は5100であり、且つMw/Mn=1.6であった。前記一般式(3)で示される構造単位と前記一般式(4)で示される構造単位との構造単位比は0.133:1であった。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表5に示した如く、n−ブチルアクリレート50.0質量部、アクリロキシプロピルトリメトキシシラン2.34質量部、さらにメルカプトプロピルトリメトキシシラン3.93質量部加え、80℃に加熱した。THF5mLに溶かしたAIBN2.48質量部を3時間かけて滴下し、さらに6時間80℃反応させ、ビニル系樹脂X1を得た。得られたビニル系樹脂X1の数平均分子量は5000であり、かつMw/Mn=1.6であった。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表5に示した如く、n−ブチルアクリレート50.0質量部、メタクリロキシプロピルトリメトキシシラン2.48質量部、さらにメルカプトプロピルトリメトキシシラン3.93質量部加え、80℃に加熱した。THF5mLに溶かしたAIBN2.48質量部を3時間かけて滴下し、さらに6時間80℃反応させ、ビニル系樹脂X2を得た。得られたビニル系樹脂X2の数平均分子量は5000であり、かつMw/Mn=1.6であった。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表5に示した如く、酢酸エチル40質量部入れ、80℃に加熱した。別の容器にメチルメタクリレート62.4質量部、ステアリルメタクリレート45.58質量部、メタクリロキシプロピルトリメトキシシラン1.99質量部、メルカプトプロピルトリメトキシシラン7.60質量部、AIBN2.60質量部を混合し、それを3時間かけて滴下し、さらに6時間80℃反応させ、ビニル系樹脂X3を得た。得られたビニル系樹脂X3の数平均分子量は5000であり、かつMw/Mn=1.6であった。
攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、表5に示した如く、ラウリルメタクリレート50.0質量部、メタクリロキシプロピルトリメトキシシラン2.48質量部、さらにメルカプトプロピルトリメトキシシラン3.93質量部加え、80℃に加熱した。THF5mLに溶かしたAIBN2.48質量部を3時間かけて滴下し、さらに6時間80℃反応させ、ビニル系樹脂X4を得た。得られたビニル系樹脂X4の数平均分子量は5000であり、かつMw/Mn=1.6であった。
n−ブチルアクリレート:東京化成工業(株)製
メチルメタクリレート:商品名「ライトエステルM」、共栄社(株)製
ステアリルメタクリレート:商品名「ライトエステルS」、共栄社(株)製
2−エチルヘキシルメタクリレート:商品名「ライトエステルEH」、共栄社(株)製
ラウリルメタクリレート:商品名「ライトエステルL」、共栄社(株)製
N,N−ジメチルアクリルアミド、(株)興人製
N,N−ジメチルアミノエチルアクリレート、(株)興人製
アクリロキシメチルトリメトキシシラン:Gelest社製
アクリロキシメチルジメチルメトキシシラン:Gelest社製
アクリロキシメチルメチルジメトキシシラン:Gelest社製
メタクリロキシメチルトリメトキシシラン:Gelest社製
メルカプトメチルトリメトキシシラン:商品名「LS535」、信越化学工業(株)製
メルカプトプロピルトリメトキシシラン:商品名「KBM803」、信越化学工業(株)製
メルカプトプロピルメチルジメトキシシラン:商品名「KBM802」、信越化学工業(株)製
THF:テトラヒドロフラン、和光純薬工業(株)製
AIBN:2,2’−アゾビスイソブチロニトリル(V−60、和光純薬工業(株)製)
BPO:ベンゾイルパーオキサイド(ナイパーBW、日脂(株)製)
ADVN:2,2’−アゾビス(2,4−ジメチルバレロニトリル)(V−65、和光純薬工業(株)製)
アクリロキシプロピルトリメトキシシラン:商品名「KBM5103」、信越化学工業(株)製
メタクリロキシプロピルトリメトキシシラン:商品名「KBM503」、信越化学工業(株)製
ラウリルメルカプタン:東京化成工業(株)製
酢酸エチル:和光純薬工業(株)製
ジルコノセンジクロライド、東京化成工業(株)製
ルテノセンジクロライド、東京化成工業(株)製
メチル2−ブロモプロピオネート、東京化成工業(株)製
プロピレンカーボネート、東京化成工業(株)製
CuBr、東京化成工業(株)製
N,N,N’,N’’,N’’−ペンタメチレンジエチレントリアミン、Aldrich社製
Claims (6)
- 前記(B)硬化触媒がアミン化合物であることを特徴とする請求項1記載の硬化性組成物。
- 前記反応が、フリーラジカル重合又はリビングラジカル重合であることを特徴とする請求項1〜3のいずれか1項記載の硬化性組成物。
- 前記(A)ビニル系樹脂100質量部に対して、前記(B)硬化触媒を0.000001〜10質量部配合することを特徴とする請求項1〜4のいずれか1項記載の硬化性組成物。
- 接着剤に用いられることを特徴とする請求項1〜5のいずれか1項記載の硬化性組成物。
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