JP7167424B2 - 一液型エポキシ樹脂組成物、硬化物、及びその用途 - Google Patents
一液型エポキシ樹脂組成物、硬化物、及びその用途 Download PDFInfo
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- JP7167424B2 JP7167424B2 JP2017199412A JP2017199412A JP7167424B2 JP 7167424 B2 JP7167424 B2 JP 7167424B2 JP 2017199412 A JP2017199412 A JP 2017199412A JP 2017199412 A JP2017199412 A JP 2017199412A JP 7167424 B2 JP7167424 B2 JP 7167424B2
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- epoxy resin
- resin composition
- acrylic copolymer
- composition according
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 58
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- 239000000178 monomer Substances 0.000 claims description 39
- 238000001723 curing Methods 0.000 claims description 32
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 8
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
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Description
本発明の一液型エポキシ樹脂組成物は、エポキシ樹脂(A)とケチミン系硬化剤(B)とを含有し、更に、各種性能を付与するためにグルシジルエーテル基を有するアクリル系共重合体(C)を必須の成分とすることを特徴とする。
の何れかで表される構造部位である。]
カラム:東ソー株式会社製の下記のカラムを直列に接続して使用した。
「TSKgel G5000」(7.8mmI.D.×30cm)×1本
「TSKgel G4000」(7.8mmI.D.×30cm)×1本
「TSKgel G3000」(7.8mmI.D.×30cm)×1本
「TSKgel G2000」(7.8mmI.D.×30cm)×1本
検出器:RI(示差屈折計)
カラム温度:40℃
溶離液:テトラヒドロフラン(THF)
流速:1.0mL/分
注入量:100μL(試料濃度4mg/mLのテトラヒドロフラン溶液)
標準試料:東ソー株式会社製 単分散ポリスチレンを用いて検量線を作成した。
塩酸-ピリジン法により測定した。樹脂に、塩酸-ピリジン溶液25mlを加え、130℃で1時間、加熱溶解した後、フェノールフタレインを指示薬として0.1N-水酸化カリウムアルコール溶液で滴定した。消費した0.1N-水酸化カリウムアルコール溶液の量によってエポキシ当量を算出した。
DSC法(示差走査熱量測定法)により求めた。
測定装置:示差走査熱量計(TA INSTRUMENTS株式会社製「DSC Q-100」)
雰囲気条件:窒素雰囲気下
温度範囲:-50~150℃
昇温速度:5℃/分
攪拌機、温度計、冷却管及び窒素導入管を備えた反応容器に、キシレン470質量部を仕込み、窒素雰囲気下に135℃にまで昇温した。そこへ、スチレン(以下、「St」と略記する。)25質量部、メチルメタクリレート(以下、「MMA」と略記する。)42質量部、2-エチルヘキシルメタクリレート(以下、「2EHMA」と略記する。)3質量部、グリシジルメタクリレート(以下、「GMA」と略記する。)30質量部およびtert-ブチルパーオキシ-2-エチルヘキサノエート(以下、「P-O」と略記する。)5質量部とからなる混合物を6時間かけて滴下した。滴下終了後も同温度にて10時間保持し、重合反応を行った後、170℃で20mmHgの減圧下に溶剤をのぞき、エポキシ当量500、重量平均分子量7,000、ガラス転移温度67℃なる固形アクリル樹脂を得た。以下、これをアクリル系共重合体(C-1)と略記する。
単量体及び重合開始剤の組成を、St20質量部、MMA37質量部、2EHMA13質量部、GMA30質量部、およびP-O 7質量部に変更した以外は合成例1と同様に操作することにより、重量平均分子量7,000、ガラス転移温度56℃なる固形アクリル樹脂を得た。以下、これをアクリル系共重合体(C-2)と略記する。
単量体及び重合開始剤の組成を、St3質量部、MMA74質量部、2EHMA3質量部、GMA20質量部およびP-O 7質量部に変更した以外は合成例1と同様に操作することにより、エポキシ当量800、重量平均分子量4,000、ガラス転移温度59℃なる固形アクリル樹脂を得た。以下、これをアクリル系共重合体(C-3)と略記する。
単量体及び重合開始剤の組成を、St15質量部、MMA25質量部、2EHMA20質量部、GMA40質量部およびP-O 3質量部に変更した以外は合成例1と同様に操作することにより、エポキシ当量400、重量平均分子量10,000、ガラス転移温度61℃なる固形アクリル樹脂を得た。以下、これをアクリル系共重合体(C-4)と略記する。
単量体及び重合開始剤の組成を、St20質量部、MMA37質量部、イソブチルアクリレート(以下、「IBA」と略記する。)13質量部、GMA30質量部およびP-O 5質量部に変更した以外は合成例1と同様に操作することにより、エポキシ当量500、重量平均分子量7,000、ガラス転移温度49℃なる固形アクリル樹脂を得た。以下、これをアクリル系共重合体(C-5)と略記する。
単量体及び重合開始剤の組成を、St20質量部、MMA43質量部、n-ブチルメタクリレート(以下、「BMA」と略記する。)17質量部、GMA20質量部およびP-O 5質量部に変更した以外は合成例1と同様に操作することにより、エポキシ当量800、重量平均分子量7,000、ガラス転移温度68℃なる固形アクリル樹脂を得た。以下、これをアクリル系共重合体(C-6)と略記する。
単量体及び重合開始剤の組成を、St32質量部、MMA43質量部、n-ブチルメタクリレート25質量部、およびP-O 5質量部に変更した以外は合成例1と同様に操作することにより、重量平均分子量7,000、ガラス転移温度78℃なるグリシジルエーテル基を有しない固形アクリル樹脂を得た。以下、これをアクリル系共重合体(C-7)と略記する。
合成例1で得られたアクリル系共重合体(C-1)15質量部とフェニルグリシジルエーテル(DIC株式会社製EPICLON 520)15質量部を混合均一とした後、ビスフェノールA型エポキシ樹脂(DIC株式会社製 EPICLON 850)と混合した。さらにケチミン系硬化剤(Air Products社製 Ancamine 2459)20質量部、およびオルソ蟻酸トリメチル(日宝化学株式会社製、OFM)5質量部を加え、自転公転攪拌機で均一に混合することで粘度 約500mPa・sの一液型エポキシ樹脂組成物(1)を得た。
表1に示す配合量比に従って、参考例1の要領で混合操作することにより、均一な一液型エポキシ樹脂組成物(2)~(6)を得た。
表1に示す配合量比に従って、参考例1の要領で混合操作することにより、均一な一液型エポキシ樹脂組成物(7)~(8)を得た。
東機産業株式会社 製 E型粘度計TVE-25Hで、25℃での粘度を測定した。
表1に従って調製した一液型エポキシ樹脂組成物をアルミ内蓋付ガラス瓶に空隙率10%以下で充填、密閉し、25℃環境下で1ヶ月放置したのち、25℃での外観、粘度上昇を確認した。初期外観からの変化の有無、初期粘度から2倍変化を目処に優劣を判断した。
組成物を厚み0.5mm、幅25mm、長さ200mmのアルミ上に、シリンジを使用して接着有効長さ150mmとなるように塗布した。接着剤上に平均粒径200μmのガラスビーズをまぶし、同形のアルミ板を貼合した。四方をクリップで固定し、25℃、65%RH環境で1週間放置し硬化したものを評価サンプルとした。
株式会社 島津製作所 製 オートグラフAG-Is 速度 100mm/min.
アルミ板を厚み0.5mm、幅25mm、長さ100mmとして、接着有効長さを端部から10mmとした以外は、T字剥離強度の評価サンプルと同様に作成、硬化した。
株式会社 島津製作所 製 オートグラフAG-X plus 引張り速度 2mm/min.
Claims (13)
- エポキシ樹脂(A)と、ケチミン系硬化剤(B)と、グリシジル基を有するアクリル系共重合体(C)とを含有する一液型エポキシ樹脂組成物であって、
前記エポキシ樹脂(A)が、一分子中にエポキシ基を2個以上有するエポキシ樹脂(a1)と、単官能性のエポキシ樹脂(a2)とを併用するものであり、
前記単官能性のエポキシ樹脂(a2)が、フェニルグリシジルエーテルを含むものであり、
前記アクリル系共重合体(C)が、グリシジル(メタ)アクリレート(c1)とその他のアクリル系単量体(c2)とスチレンとの共重合体であり、
前記その他のアクリル系単量体(c2)が、イソブチル(メタ)アクリレートを含むものであり、
前記スチレンの含有量が、前記アクリル系共重合体(C)の原料単量体中に1~23質量%の範囲であることを特徴とする一液型エポキシ樹脂組成物。 - 前記エポキシ樹脂(A)のエポキシ当量が150~1500g/eqの範囲である請求項1記載の一液型エポキシ樹脂組成物。
- 前記アクリル系共重合体(C)の重量平均分子量が3000~25000の範囲である請求項1又は2記載の一液型エポキシ樹脂組成物。
- 前記アクリル系共重合体(C)のエポキシ当量が200~1000g/eqの範囲である請求項1~3の何れか1項記載の一液型エポキシ樹脂組成物。
- 前記ケチミン系硬化剤(B)が、分子中の第1級アミノ基が全てカルボニル化合物でブロック化されたポリアミン化合物(b1)である請求項1~4の何れか1項記載の一液型エポキシ樹脂組成物。
- 更に脱水剤(D)を含有する請求項1~5の何れか1項記載の一液型エポキシ樹脂組成物。
- 前記脱水剤(D)がオルトエステルである請求項6記載の一液型エポキシ樹脂組成物。
- 前記エポキシ樹脂(A)と、前記ケチミン系硬化剤(B)と、前記アクリル系共重合体(C)と前記脱水剤(D)との混合粘度が、100~2,000mPa・sの範囲である請求項6又は7記載の一液型エポキシ樹脂組成物。
- 前記エポキシ樹脂(A)と前記アクリル系共重合体(C)との使用割合が、(A)/(C)で表される質量比で30/70~98/2の範囲である請求項1~8の何れか1項記載の一液型エポキシ樹脂組成物。
- 前記エポキシ樹脂(A)と前記アクリル系共重合体(C)との合計100質量部に対し、前記ケチミン系硬化剤(B)を5~80質量部で用いる請求項1~9の何れか1項記載の一液型エポキシ樹脂組成物。
- 請求項1~10の何れか一つに記載の一液型エポキシ樹脂組成物を湿気硬化させた硬化物。
- 請求項1~10の何れか一つに記載の一液型エポキシ樹脂組成物からなるプライマー。
- 請求項1~10の何れか一つに記載の一液型エポキシ樹脂組成物からなる補修用注入剤。
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JP2000034336A (ja) | 1998-07-17 | 2000-02-02 | Yokohama Rubber Co Ltd:The | 一液型常温湿気硬化性アクリル樹脂組成物およびその用途 |
JP2003342518A (ja) | 2002-05-30 | 2003-12-03 | Kansai Paint Co Ltd | 塗料組成物 |
JP2006096834A (ja) | 2004-09-29 | 2006-04-13 | Toagosei Co Ltd | エポキシ樹脂を含有する接着剤組成物 |
JP2019099585A (ja) | 2017-11-28 | 2019-06-24 | Dic株式会社 | 一液型エポキシ樹脂組成物、硬化物、及びその用途 |
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JP2000034336A (ja) | 1998-07-17 | 2000-02-02 | Yokohama Rubber Co Ltd:The | 一液型常温湿気硬化性アクリル樹脂組成物およびその用途 |
JP2003342518A (ja) | 2002-05-30 | 2003-12-03 | Kansai Paint Co Ltd | 塗料組成物 |
JP2006096834A (ja) | 2004-09-29 | 2006-04-13 | Toagosei Co Ltd | エポキシ樹脂を含有する接着剤組成物 |
JP2019099585A (ja) | 2017-11-28 | 2019-06-24 | Dic株式会社 | 一液型エポキシ樹脂組成物、硬化物、及びその用途 |
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