JP7180822B2 - 硬化性組成物、硬化物及び接着剤 - Google Patents
硬化性組成物、硬化物及び接着剤 Download PDFInfo
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- JP7180822B2 JP7180822B2 JP2022549674A JP2022549674A JP7180822B2 JP 7180822 B2 JP7180822 B2 JP 7180822B2 JP 2022549674 A JP2022549674 A JP 2022549674A JP 2022549674 A JP2022549674 A JP 2022549674A JP 7180822 B2 JP7180822 B2 JP 7180822B2
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Classifications
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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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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Description
カラム ; 東ソー株式会社製ガードカラムHXL-H
+東ソー株式会社製 TSKgel G5000HXL
+東ソー株式会社製 TSKgel G4000HXL
+東ソー株式会社製 TSKgel G3000HXL
+東ソー株式会社製 TSKgel G2000HXL
検出器 ; RI(示差屈折計)
データ処理:東ソー株式会社製 SC-8010
測定条件: カラム温度 40℃
溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 ;ポリスチレン
試料 ;樹脂固形分換算で0.4質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
窒素雰囲気下でポリオキシエチレン-ポリオキシプロピレンコポリマーであるポリエーテルポリオール(三井ケミカル&SKCポリウレタン社製「アクトコールEP-530」、Mn:3000、官能基数:3)638質量部、イソホロンジイソシアネート(住化コベストロウレタン社製「デスモジュールI」)142質量部を混合し、触媒としてジオクチルスズジアセテート(日東化成株式会社製「ネオスタン U-820」)0.1質量部を投入し、80℃で5時間反応させ、次いで、ブロック化剤としてカルダノール(Cardolite社製「NX2021」)220質量部を投入し90℃で5時間反応させて、ブロックイソシアネートプレポリマー(1)を得た。
下記表1に示す割合で各成分を配合し、合成例1と同様の方法にて、ブロックイソシアネートプレポリマー(2)~(13)を得た。
EP-530:ポリオキシエチレン-ポリオキシプロピレンコポリマー(三井ケミカル&SKCポリウレタン社製「EP-530」、Mw:3000、官能基数:3)
ED-37A:ポリオキシエチレン-ポリオキシプロピレンコポリマー(三井ケミカル&SKCポリウレタン社製「ED-37A」、Mw:3000、官能基数:2)
T-3000:ポリプロピレングリコール(三井ケミカル&SKCポリウレタン社製「T-3000」、Mw:3000、官能基数:3)
EP-3033:ポリプロピレングリコール(三井ケミカル&SKCポリウレタン社製「EP-3033」、Mw:6600、官能基数:4)
PTMG-3000:ポリテトラメチレングリコール(三菱ケミカル株式会社製「PTMG-3000」、Mw:3000、官能基数:2)
T5652:ポリカーボネートポリオール(旭化成株式会社製「DURANOL T5652」、Mw:2000、官能基数:2)
D-3000:ポリプロピレングリコール(三井ケミカル&SKCポリウレタン社製「D-3000」、Mw:3000、官能基数:2)
IPDI:イソホロンジイソシアネート(住化コベストロウレタン社製「デスモジュールI」)
TDI:トリレンジイソシアネート(三井ケミカル&SKCポリウレタン社製「T-80」)
HDI:ヘキサメチレンジイソシアネート(住化コベストロウレタン社製「デスモジュールH」)
H12MDI:ジシクロヘキシルメタン4,4’-ジイソシアネート(住化コベストロウレタン社製「デスモジュールW」)
PDDP:パラドデシルフェノール(SI Group社製「Para-Dodecylphenol」、炭素原子数12個の炭化水素基を有するフェノール化合物)
NX-2021:カルダノール(Cardolite社製「NX-2021」、炭素原子数15個の炭化水素基を有するフェノール化合物)
NX-2026:カルダノール(Cardolite社製「NX-2026」、炭素原子数15個の炭化水素基を有するフェノール化合物)
PTBP:パラターシャリーブチルフェノール(DIC株式会社製「DIC-PTBP」)
PNP:パラノニルフェノール(SI Group社製「Tech.grade」)
合成例1で得たブロックイソシアネートプレポリマー(1)20質量部、ゴム変性エポキシ樹脂(DIC株式会社製「EPICLON TSR-601」)5質量部、ビスフェノールA型エポキシ樹脂(DIC株式会社製「EPICLON 850-S」)75質量部、硬化剤としてジシアンジアミド5質量部、硬化促進剤として3,4-ジクロロフェニル-N,N-ジメチル尿素1質量部、フィラーとして炭酸カルシウム20質量部を混合し、硬化性組成物(1)を得た。
実施例1で用いたブロックイソシアネートプレポリマー(1)の代わりに、合成例2~8で得たブロックイソシアネートプレポリマー(2)~(8)を表3に示した配合量で用いた以外は、実施例1と同様にして、硬化性組成物(2)~(8)を得た。
実施例1で用いたブロックイソシアネートプレポリマー(1)の代わりに、合成例9~13で得たブロックイソシアネートプレポリマー(9)~(13)を表4に示した配合量で用いた以外は、実施例1と同様にして、硬化性組成物(R1)~(R8)を得た。
接着性の評価は、引張剪断試験及びT字剥離試験に基づいて行った。
JIS K6859(1994)(接着剤のクリープ破壊試験)及びJIS K6854-3(1999)(接着剤の剥離接着強さ試験)に従い、実施例及び比較例で得られた硬化性組成物を170℃で30分かけて硬化させ引張剪断試験及びT字剥離試験用の試験片を得た。
JIS K6859(1994)(接着剤のクリープ破壊試験)方法で25℃の条件で島津製作所株式会社製「AUTOGRAPH AG-XPlus 100kN」を用いて、前記試験片の引張剪断強度を測定した。
JIS K6854-3(1999)(接着剤の剥離接着強さ試験)方法で25℃の条件で島津製作所株式会社製「AUTOGRAPH AG-IS 1kN」を用いて前記試験片の剥離強度を測定した。
上記<引張剪断試験><T字剥離試験>で用いた試験片を50℃、90%の条件で2週間耐湿熱試験を行った後、同様の試験機で引張剪断強度を上記<引張剪断試験>に記載の方法にて測定した。
上記<引張剪断試験>に用いた試験片、及び耐湿熱試験後<引張剪断試験>の試験片について、目視にて凝集破壊面積比率(CF面積比率)を確認し、試験片の破壊状態を確認した。前記凝集破壊面積比率が高いほど、破壊状態が良い。また、耐湿熱試験後であっても凝集破壊面積比率が高い物は耐湿熱性に優れる。
TSR-601:ゴム変性エポキシ樹脂(DIC株式会社製「EPICLON TSR-601」)
850-S:ビスフェノールA型エポキシ樹脂(DIC株式会社製「EPICLON 850-S」)
830-S:ビスフェノールF型液状エポキシ樹脂(DIC株式会社製「EPICLON 830-S」、エポキシ等量:170g/eq)
DICY:ジシアンジアミド
DCMU:3,4-ジクロロフェニル-N,N-ジメチル尿素
Claims (10)
- ポリオール化合物(a1)、ポリイソシアネート化合物(a2)、ブロック化剤(a3)を必須原料とするブロックイソシアネートプレポリマー(A)と、
エポキシ樹脂(B)と、
硬化剤(C)とを含有する硬化性組成物であって、
前記ブロック化剤(a3)が、カルダノールであることを特徴とする硬化性組成物。 - 前記ポリオール化合物(a1)が、ポリエーテルポリオールである請求項1記載の硬化性組成物。
- 前記ポリオール化合物(a1)が、ポリオキシエチレンユニットと、ポリオキシプロピレンユニットとを含むものである請求項1又は2記載の硬化性組成物。
- 前記ポリオール化合物(a1)が、ポリオキシエチレン-ポリオキシプロピレン共重合体である請求項1~3の何れか1項記載の硬化性組成物。
- 前記ポリイソシアネート化合物(a2)が、ジイソシアネートである請求項1~4の何れか1項記載の硬化性組成物。
- 前記硬化剤(C)がジシアンジアミドを含むものである請求項1~5の何れか1項記載の硬化性組成物。
- 前記エポキシ樹脂(B)のエポキシ当量が150~250g/eqの範囲である請求項1~6の何れか1項記載の硬化性組成物。
- 前記ブロックイソシアネートプレポリマー(A)と前記エポキシ樹脂(B)との質量割合[(A)/(B)]が、10/90~30/70の範囲である請求項1~7の何れか1項記載の硬化性組成物。
- 請求項1~8の何れか1項記載の硬化性組成物の硬化物。
- 請求項1~8の何れか1項記載の硬化性組成物からなる接着剤。
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