JP6658747B2 - エポキシ樹脂組成物、プリプレグ、繊維強化プラスチック材料および繊維強化プラスチック材料の製造方法 - Google Patents
エポキシ樹脂組成物、プリプレグ、繊維強化プラスチック材料および繊維強化プラスチック材料の製造方法 Download PDFInfo
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- JP6658747B2 JP6658747B2 JP2017518306A JP2017518306A JP6658747B2 JP 6658747 B2 JP6658747 B2 JP 6658747B2 JP 2017518306 A JP2017518306 A JP 2017518306A JP 2017518306 A JP2017518306 A JP 2017518306A JP 6658747 B2 JP6658747 B2 JP 6658747B2
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- SOLNRIROLBHRDJ-UHFFFAOYSA-N propyl 3-nitrobenzoate Chemical compound CCCOC(=O)C1=CC=CC([N+]([O-])=O)=C1 SOLNRIROLBHRDJ-UHFFFAOYSA-N 0.000 description 1
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000009849 vacuum degassing Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- 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
- C08G59/40—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 curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
-
- 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
- C08G59/40—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 curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
-
- 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
- C08G59/40—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 curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4223—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof aromatic
-
- 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
- C08G59/40—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 curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
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- 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
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- C08G59/40—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 curing agents used
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Description
本願は、2014年12月2日出願の米国仮特許出願第62/086,428号および2015年10月29日出願の米国仮特許出願第62/248,012号の優先権ならびに利益を主張し、その開示内容は、あらゆる目的のためにその全体が参照により本明細書に組み込まれる。
(1)エポキシ樹脂組成物であって、
(a)トリグリシジルアミン類、テトラグリシジルアミン類、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、レゾルシノール型エポキシ樹脂、ナフタレン型エポキシ樹脂、ジシクロペンタジエン型エポキシ樹脂、ビフェニル骨格を有するエポキシ樹脂、イソシアネート変性エポキシ樹脂、脂環式エポキシ樹脂またはトリフェニルメタン型エポキシ樹脂の少なくとも1つより選択される少なくとも1種のエポキシ樹脂と、
(b)少なくとも1種のジシアンジアミドと、
(c)少なくとも1種の芳香族ウレアと、
(d)(d1)カルボン酸化合物およびテトラキスフェノール化合物からなる群より選択される少なくとも1種の化合物と(d2)イミダゾールおよびイミダゾリンからなる群より選択される少なくとも1種のエポキシ樹脂硬化促進剤とを含む、少なくとも1種の包接錯体とを含み、
(b)が全エポキシ樹脂100重量部当たり3〜7重量部の範囲であり、
(c)が全エポキシ樹脂100重量部当たり0.5〜7重量部の範囲であり、
(d)包接錯体が、エポキシ樹脂組成物の全重量を基準として1〜5重量%の範囲の量で存在するエポキシ樹脂組成物。
(2)実施形態(1)のエポキシ樹脂組成物からなるプリプレグ。
(3)実施形態(2)のプリプレグを硬化させてなる繊維強化プラスチック材料。
カルボン酸化合物
R(COOH)n1 (IV)
安息香酸、2−メチル安息香酸、3−メチル安息香酸、4−メチル安息香酸、2−エチル安息香酸、3−エチル安息香酸、4−エチル安息香酸、2−n−プロピル安息香酸、3−n−プロピル安息香酸、4−n−プロピル安息香酸、2−ブチル安息香酸、3−ブチル安息香酸、4−ブチル安息香酸、2−1−プロピル安息香酸、3−1−プロピル安息香酸、4−1−プロピル安息香酸、2−1−ブチル安息香酸、3−1−ブチル安息香酸、4−1−ブチル安息香酸、2−ヒドロキシ安息香酸、3−ヒドロキシ安息香酸、4−ヒドロキシ安息香酸、4−イソプロピル安息香酸、2−ニトロ安息香酸、3−ニトロ安息香酸、4−ニトロ安息香酸、2−ニトロ安息香酸メチル、3−ニトロ安息香酸メチル、4−ニトロ安息香酸メチル、2−ニトロ安息香酸エチル、3−ニトロ安息香酸エチル、4−ニトロ安息香酸エチル、2−ニトロ安息香酸プロピル、3−ニトロ安息香酸プロピル、4−ニトロ安息香酸プロピル、2−ニトロ安息香酸ブチル、3−ニトロ安息香酸ブチル、4−ニトロ安息香酸ブチル、2,3−ジメチル安息香酸、2,4−ジメチル安息香酸、2,5−ジメチル安息香酸、2,6−ジメチル安息香酸、3,4−ジメチル安息香酸、3,5−ジメチル安息香酸、2,3,4−トリメチル安息香酸、2,3,5−トリメチル安息香酸、2,4,5−トリメチル安息香酸、2,4,6−トリメチル安息香酸、3,4,5−トリメチル安息香酸、3,6−ジメチル安息香酸、4,5−ジメチル安息香酸、4,6−ジメチル安息香酸、2,3−ジエチル安息香酸、2,4−ジエチル安息香酸、2,5−ジエチル安息香酸、2,6−ジエチル安息香酸、3,4−ジエチル安息香酸、3,5−ジエチル安息香酸、3,6−ジエチル安息香酸、4,5−ジエチル安息香酸、4,6−ジエチル安息香酸、2,3−ジヒドロキシ安息香酸、2,4−ジヒドロキシ安息香酸、2,5−ジヒドロキシ安息香酸、2,6−ジヒドロキシ安息香酸、3,4−ジヒドロキシ安息香酸、3,5−ジヒドロキシ安息香酸、3,6−ジヒドロキシ安息香酸、4,5−ジヒドロキシ安息香酸、4,6−ジヒドロキシ安息香酸、2−ヒドロキシ−3−メチル安息香酸、2−ヒドロキシ−4−メチル安息香酸、2−ヒドロキシ−5−メチル安息香酸、4−ヒドロキシ−3−メトキシ安息香酸、3−ヒドロキシ−4−メトキシ安息香酸、3,4−ジメトキシ安息香酸、2,4−ジメトキシ安息香酸、2,4−ジヒドロキシ−6−メチル安息香酸、3,4,5−トリヒドロキシ安息香酸、4−ヒドロキシ−3,5−ジメトキシ安息香酸、2,4,5−トリメトキシ安息香酸、2−(カルボキシメチル)安息香酸、3−(カルボキシメチル)安息香酸、4−(カルボキシメチル)安息香酸、2−(カルボキシカルボニル)安息香酸、3−(カルボキシカルボニル)安息香酸、4−(カルボキシカルボニル)安息香酸等の安息香酸化合物およびこれらのエステル(例えば、炭素数1〜6のアルキルエステル);
フタル酸、3−メチルフタル酸、4−メチルフタル酸、5−メチルフタル酸、6−メチルフタル酸、3−エチルフタル酸、4−エチルフタル酸、5−エチルフタル酸、6−エチルフタル酸、3−n−プロピルフタル酸、4−n−プロピルフタル酸、5−n−プロピルフタル酸、6−n−プロピルフタル酸、3−ブチルフタル酸、4−ブチルフタル酸、5−ブチルフタル酸、6−ブチルフタル酸、3−1−プロピルフタル酸、4−i−プロピルフタル酸、5−i−プロピルフタル酸、6−i−プロピルフタル酸、3−i−ブチルフタル酸、4−i−ブチルフタル酸、5−i−ブチルフタル酸、6−i−ブチルフタル酸、3−ヒドロキシフタル酸、4−ヒドロキシフタル酸、5−ヒドロキシフタル酸、6−ヒドロキシフタル酸、3,4−ジヒドロキシフタル酸、3,5−ジヒドロキシフタル酸、3,6−ジヒドロキシフタル酸、4,5−ジヒドロキシフタル酸、4,6−ジヒドロキシフタル酸、2,3−ジメトキシフタル酸、4,5−ジメトキシフタル酸、3−ニトロフタル酸、4−ニトロフタル酸、5−ニトロフタル酸、6−ニトロフタル酸、3,4−ジメチルフタル酸、3,5−ジメチルフタル酸、3,6−ジメチルフタル酸、4,5−ジメチルフタル酸、4,6−ジメチルフタル酸等のフタル酸化合物およびこれらのエステル(例えば、炭素数1〜6のアルキルエステル);
イソフタル酸、2−メチルイソフタル酸、4−メチルイソフタル酸、5−メチルイソフタル酸、6−メチルイソフタル酸、2−エチルイソフタル酸、4−エチルイソフタル酸、5−エチルイソフタル酸、6−エチルイソフタル酸、2−n−プロピルイソフタル酸、4−n−プロピルイソフタル酸、5−n−プロピルイソフタル酸、6−n−プロピルイソフタル酸、2−イソプロピルイソフタル酸、4−イソプロピルイソフタル酸、5−イソプロピルイソフタル酸、6−イソプロピルイソフタル酸、2−ブチルイソフタル酸、4−ブチルイソフタル酸、5−ブチルイソフタル酸、6−ブチルイソフタル酸、2−イソブチルイソフタル酸、4−イソブチルイソフタル酸、5−イソブチルイソフタル酸、6−イソブチルイソフタル酸、4−t−ブチルイソフタル酸、5−t−ブチルイソフタル酸、6−t−ブチルイソフタル酸、2−ヒドロキシイソフタル酸、4−ヒドロキシイソフタル酸、5−ヒドロキシイソフタル酸、6−ヒドロキシイソフタル酸、2,4−ジヒドロキシイソフタル酸、2,5−ジヒドロキシイソフタル酸、2,6−ジヒドロキシイソフタル酸、4,5−ジヒドロキシイソフタル酸、4,6−ジヒドロキシイソフタル酸、5,6−ジヒドロキシイソフタル酸、2,4−ジメチルイソフタル酸、2,5−ジメチルイソフタル酸、2,6−ジメチルイソフタル酸、4,5−ジメチルイソフタル酸、4,6−ジメチルイソフタル酸、5,6−ジメチルイソフタル酸、2−ニトロイソフタル酸、4−ニトロイソフタル酸、5−ニトロイソフタル酸、6−ニトロイソフタル酸等のイソフタル酸化合物およびこれらのエステル(例えば、炭素数1〜6のアルキルエステル);
テレフタル酸、2−メチルテレフタル酸、2−エチルテレフタル酸、2−n−プロピルテレフタル酸、2−イソプロピルテレフタル酸、2−ブチルテレフタル酸、2−イソブチルテレフタル酸、2−ヒドロキシテレフタル酸、2,6−ジヒドロキシテレフタル酸、2,6−ジメチルテレフタル酸、2−ニトロテレフタル酸等のテレフタル酸化合物;1,2,3−ベンゼントリカルボン酸、1,2,4−ベンゼントリカルボン酸(トリメリット酸)、1,2,5−ベンゼントリカルボン酸、1,3,4−ベンゼントリカルボン酸、1,3,5−ベンゼントリカルボン酸(トリメシン酸)、4−ヒドロキシ−1,2,3−ベンゼントリカルボン酸、5−ヒドロキシ−1,2,3−ベンゼントリカルボン酸、3−ヒドロキシ−1,2,4−ベンゼントリカルボン酸、5−ヒドロキシ−1,2,4−ベンゼントリカルボン酸、6−ヒドロキシ−1,2,4−ベンゼントリカルボン酸等のベンゼントリカルボン酸化合物;1,2,3,4−ベンゼンテトラカルボン酸、1,2,3,5−ベンゼンテトラカルボン酸、1,2,4,5−ベンゼンテトラカルボン酸(ピロメリット酸)等のテトラカルボン酸化合物;ベンゼンヘキサカルボン酸;およびこれらのエステル(例えば、炭素数1〜6のアルキルエステル);
1−ナフトエ酸、2−ナフトエ酸、2−メチル−1−ナフトエ酸、3−メチル−1−ナフトエ酸、4−メチル−1−ナフトエ酸、5−メチル−1−ナフトエ酸、6−メチル−1−ナフトエ酸、7−メチル−1−ナフトエ酸、8−メチル−1−ナフトエ酸、1−メチル−2−ナフトエ酸、3−メチル−2−ナフトエ酸、4−メチル−2−ナフトエ酸、5−メチル−2−ナフトエ酸、6−メチル−2−ナフトエ酸、7−メチル−2−ナフトエ酸、8−メチル−2−ナフトエ酸、1,2−ナフタレンジカルボン酸、1,3−ナフタレンジカルボン酸、1,4−ナフタレンジカルボン酸、1,5−ナフタレンジカルボン酸、1,6−ナフタレンジカルボン酸、1,7−ナフタレンジカルボン酸、1,8−ナフタレンジカルボン酸、2,3−ナフタレンジカルボン酸、2,4−ナフタレンジカルボン酸、2,5−ナフタレンジカルボン酸、2,6−ナフタレンジカルボン酸、2,7−ナフタレンジカルボン酸、2,8−ナフタレンジカルボン酸、2−ヒドロキシル−1−ナフトエ酸、3−ヒドロキシ−1−ナフトエ酸、4−ヒドロキシ−1−ナフトエ酸、5−ヒドロキシル−1−ナフトエ酸、6−ヒドロキシ−1−ナフトエ酸、7−ヒドロキシ−1−ナフトエ酸、8−ヒドロキシ−1−ナフトエ酸、1−ヒドロキシ−2−ナフトエ酸、3−ヒドロキシ−2−ナフトエ酸、4−ヒドロキシ−2−ナフトエ酸、5−ヒドロキシ−2−ナフトエ酸、6−ヒドロキシ−2−ナフトエ酸、7−ヒドロキシ−2−ナフトエ酸、8−ヒドロキシ−2−ナフトエ酸、1,2,4,5−ナフタレンテトラカルボン酸、2,3−ジヒドロキシ−1−ナフトエ酸、2,4−ジヒドロキシ−1−ナフトエ酸、2,5−ジヒドロキシ−1−ナフトエ酸、2,6−ジヒドロキシ−1−ナフトエ酸、2,7−ジヒドロキシ−1−ナフトエ酸、2,8−ジヒドロキシ−1−ナフトエ酸、3,4−ジヒドロキシ−1−ナフトエ酸、3,5−ジヒドロキシ−1−ナフトエ酸、3,6−ジヒドロキシ−1−ナフトエ酸、3,7−ジヒドロキシ−1−ナフトエ酸、3,8−ジヒドロキシ−1−ナフトエ酸、4,5−ジヒドロキシ−1−ナフトエ酸、4,6−ジヒドロキシ−1−ナフトエ酸、4,7−ジヒドロキシ−1−ナフトエ酸、4,8−ジヒドロキシ−1−ナフトエ酸、5,6−ジヒドロキシ−1−ナフトエ酸、5,7−ジヒドロキシ−1−ナフトエ酸、5,8−ジヒドロキシ−1−ナフトエ酸、6,7−ジヒドロキシ−1−ナフトエ酸、6,8−ジヒドロキシ−1−ナフトエ酸、7,8−ジヒドロキシ−1−ナフトエ酸、1,3−ジヒドロキシ−2−ナフトエ酸、1,4−ジヒドロキシ−2−ナフトエ酸、1,5−ジヒドロキシ−2−ナフトエ酸、1,6−ジヒドロキシ−2−ナフトエ酸、1,7−ジヒドロキシ−2−ナフトエ酸、1,8−ジヒドロキシ−2−ナフトエ酸、3,4−ジヒドロキシ−2−ナフトエ酸、3,5−ジヒドロキシ−2−ナフトエ酸、3,6−ジヒドロキシ−2−ナフトエ酸、3,8−ジヒドロキシ−2−ナフトエ酸、4,5−ジヒドロキシ−2−ナフトエ酸、4,6−ジヒドロキシ−2−ナフトエ酸、4,7−ジヒドロキシ−2−ナフトエ酸、4,8−ジヒドロキシ−2−ナフトエ酸、5,6−ジヒドロキシ−2−ナフトエ酸、5,7−ジヒドロキシ−2−ナフトエ酸、5,8−ジヒドロキシ−2−ナフトエ酸、6,7−ジヒドロキシ−2−ナフトエ酸、6,8−ジヒドロキシ−2−ナフトエ酸、7,8−ジヒドロキシ−2−ナフトエ酸等のナフトエ酸化合物およびこれらのエステル(例えば、炭素数1〜6のアルキルエステル);
シクロヘキサンカルボン酸、1,2−シクロヘキサンジカルボン酸、1,3−シクロヘキサンジカルボン酸、1,4−シクロヘキサンジカルボン酸、1,1−シクロヘキサンジカルボン酸等のシクロヘキサンカルボン酸化合物;1,2−デカヒドロナフタレンジカルボン酸、1,3−デカヒドロナフタレンジカルボン酸、1,4−デカヒドロナフタレンジカルボン酸、1,5−デカヒドロナフタレンジカルボン酸、1,6−デカヒドロナフタレンジカルボン酸、1,7−デカヒドロナフタレンジカルボン酸、1,8−デカヒドロナフタレンジカルボン酸等のナフタレンジカルボン酸化合物;およびこれらのエステル(例えば、炭素数1〜6のアルキルエステル)。
テトラキスフェノール
イミダゾール/イミダゾリン
エポキシ樹脂
平均EEW=(Wx+Wy+Wz)/(Wx/Ex+Wy/Ey+Wz/Ez)
η* finalは、65℃で2時間保持後の樹脂の最終粘度である
・テトラグリシジルジアミノジフェニルメタン:アラルダイト(登録商標)MY9655T(エポキシド当量(EEW):126g/eq、ハンツマン・アドバンスト・マテリアルズ社製)
・ビスフェノールA型エポキシ樹脂:「Epon(登録商標)」3002(エポキシド当量(EEW):555g/eq、モメンティブ・スペシャルティー・ケミカルズ社製)
・ビスフェノールA型エポキシ樹脂:「Epon(登録商標)」2005(エポキシド当量(EEW):1300g/eq、モメンティブ・スペシャルティー・ケミカルズ社製)
・ビスフェノールA型エポキシ樹脂:「Epon(登録商標)」828(エポキシド当量(EEW):187g/eq、モメンティブ・スペシャルティー・ケミカルズ社製)
・ジシアンジアミド:「Dyhard(登録商標)」100S(アルツケム・トロストベルク・ゲーエムベーハー社製)
・4,4’−ジアミノジフェニルスルホン(DDS)(和歌山精化工業(株)製)
・2,4’−トルエンビスジメチルウレア:「オミキュア(登録商標)」U−24M(CVCサーモセット・スペシャルティーズ社製)
・1,1,2,2−テトラキス(4−ヒドロキシフェニル)エタンと2−フェニル−4−メチル−5−ヒドロキシメチルイミダゾールの錯体:Nissocure(登録商標)TIC−188(ニッソーアメリカ社製)
・5−ヒドロキシイソフタル酸(HIPA)と2−エチル−4−メチルイミダゾールの錯体:HIPA−2E4MZ(ニッソーアメリカ社製)
・ポリビニルホルマール:「ビニレック(登録商標)」PVF−K(JNC(株)製)
・炭素繊維:「トレカ(登録商標)」T700G−24K−31E(繊維フィラメント数:24,000、引張強度:4.9GPa、引張弾性率:240GPa、引張伸度:2.0%、東レ(株)製)
硬化剤および硬化促進剤以外の全成分を、ミキサー内で所定量溶解させて混合物とした後、所定量の硬化促進剤とともに所定量の硬化剤を加えてエポキシ樹脂組成物を得た。
エポキシ樹脂組成物の硬化物を以下の方法で成形した。真空脱泡および高せん断混合の後、2mm厚の「テフロン(登録商標)」製スペーサーにより厚さ2mmになるように設定した金型に(1)で調製したエポキシ樹脂組成物を注入した。その後、以下の条件下でエポキシ樹脂組成物を硬化させて2mm厚の板状の樹脂組成物の硬化物を得た。
条件1:エポキシ樹脂組成物を50℃/分の速度で室温から163℃まで加熱した後、163℃で0.5分間保持した。
条件2:エポキシ樹脂組成物を50℃/分の速度で室温から163℃まで加熱した後、163℃で2分間保持した。
エポキシ樹脂組成物の硬化度は、硬化サイクル中の樹脂のトルクの上昇、すなわちS’を測定することにより実験的に求めることができる。ここで、完全硬化または100%硬化度とは、硬化温度における、トルクの上昇が平衡に達し上昇が止まる点(S’final)に等しい。S’finalは、動的機械的レオロジー試験装置(アルファテクノロジーズ社製APA2000)を用いて、40℃/分の速度で室温から163℃に加熱し、163℃で少なくとも30分間保持することにより測定した。S’finalを、1分超2分未満の間においてS’が上昇を開始する点とした。この点を100%硬化の点と見なすことができる。次いで、硬化中の任意の時点における硬化度%を、その点のS’値(S’t)を用いて求めることができる。次いで、エポキシ樹脂組成物の硬化物の硬化度(%)を以下の式を用いて算出した。
(2)で得たエポキシ樹脂組成物の硬化物から、12.7mm×150mmの試験片を切り出した。その後、この試験片を加工して、ASTM D5045(1999)に準拠してインストロン万能試験機(インストロン社製)を用いて試験した。試験片への初期亀裂の導入は、液体窒素温度まで冷やした剃刀の刃を試験片にあてハンマーで剃刀の背を叩いて衝撃を加えることで行った。ここで、樹脂靭性とは変形モードI(開口型)の臨界応力を指す。5つの試験片の平均値(n=5)を樹脂靭性値とした。
(1)で調製したエポキシ樹脂組成物をナイフコーターで剥離紙に塗布して、52.0g/m2の樹脂フィルムを2枚作製した。次に、作製した上記2枚の樹脂フィルムを、密度1.8g/cm2の一方向に配列されたシート状の炭素繊維(T700G−24K−31E)の両面に積層し、ローラー温度100℃、ローラー圧力0.07MPaでエポキシ樹脂組成物を含浸させて、炭素繊維の単位面積重量が190g/m2でエポキシ樹脂組成物の重量分率が35.4%の一方向プリプレグを得た。
(6)で調製したFPR材料の表面品位は、次の方法で評価した。強化繊維の配列の乱れ、エポキシ樹脂組成物の硬化物の欠陥箇所、およびFRP材料表面の空隙を目視した。これらの欠陥がない表面を高品質の表面とする。一方、これらの欠陥が1つでもある表面を欠陥表面とする。
本発明の他の実施形態においては、エポキシ樹脂組成物を65℃で2時間保持した際の粘度上昇率は、プリプレグの作製の際の加工性の観点から初期粘度の3倍未満であってもよい。
樹脂の「粘度上昇率」は、粘度測定と同じ方法で粘弾性装置(ARES、ティー・エイ・インスツルメント社製)のパラメータを設定し、65℃の温度で2時間保持することにより測定する。粘度上昇率は、下記式を用いて算出する。
η* finalは、65℃で2時間保持後の樹脂の最終粘度である
各実施例および比較例における各成分量を表1および2に示す。表1および2に示すエポキシ樹脂組成物は、(1)に記載の方法に従って得た。
Claims (16)
- エポキシ樹脂組成物であって、
(a)トリグリシジルアミン類、テトラグリシジルアミン類、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、レゾルシノール型エポキシ樹脂、ナフタレン型エポキシ樹脂、ジシクロペンタジエン型エポキシ樹脂、ビフェニル骨格を有するエポキシ樹脂、イソシアネート変性エポキシ樹脂、脂環式エポキシ樹脂またはトリフェニルメタン型エポキシ樹脂の少なくとも1つより選択されるエポキシ樹脂と、
(b)少なくとも1種のジシアンジアミドと、
(c)少なくとも1種の芳香族ウレアと、
(d)(d1)カルボン酸化合物およびテトラキスフェノール化合物からなる群より選択される少なくとも1種の化合物と(d2)イミダゾールおよびイミダゾリンからなる群より選択される少なくとも1種のエポキシ樹脂硬化促進剤とを含む、少なくとも1種の包接錯体とを含み、
(b)が全エポキシ樹脂100重量部当たり3〜7重量部の範囲であり、
(c)が全エポキシ樹脂100重量部当たり0.5〜7重量部の範囲であり、
(d)包接錯体が、エポキシ樹脂組成物の全重量を基準として1〜5重量%の範囲の量で存在するエポキシ樹脂組成物。 - 少なくとも1種のエポキシ樹脂硬化促進剤が、イミダゾール、2−エチル−4−メチルイミダゾール、1−メチルイミダゾール、2−メチルイミダゾール、4−メチルイミダゾール、1,2−ジメチルイミダゾール、1−ベンジル−2−メチルイミダゾール、2−ヘプタデシルイミダゾール、2−ウンデシルイミダゾール、2−フェニルイミダゾール、2−フェニル−4−メチル−5−ヒドロキシメチルイミダゾール、2−メチルイミダゾリン、2−フェニルイミダゾリンおよびこれらの組合せからなる群より選択されるイミダゾール化合物またはイミダゾリン化合物を含む、請求項1に記載のエポキシ樹脂組成物。
- 少なくとも1種の化合物が芳香族カルボン酸化合物を含む、請求項1〜3のいずれか一項に記載のエポキシ樹脂組成物。
- イソフタル酸化合物が、5−t−ブチルイソフタル酸、5−ニトロイソフタル酸または5−ヒドロキシイソフタル酸である、請求項6に記載のエポキシ樹脂組成物。
- (a)のエポキシ樹脂が、トリグリシジルアミン類、テトラグリシジルアミン類、ナフタレン型エポキシ樹脂、ビフェニル骨格を有するエポキシ樹脂、イソシアネート変性エポキシ樹脂、脂環式エポキシ樹脂またはトリフェニルメタン型エポキシ樹脂の少なくとも1つより選択される、請求項1〜7のいずれか一項に記載のエポキシ樹脂組成物。
- (a)のエポキシ樹脂がテトラグリシジルアミン類である請求項8に記載のエポキシ樹脂組成物。
- (a)のエポキシ樹脂が全エポキシ樹脂100重量部当たり10〜50重量部の範囲である請求項8に記載のエポキシ樹脂組成物。
- EEWが500〜10000g/eqであり全エポキシ樹脂100重量部当たり10〜40重量部の量で存在する第1のビスフェノール型エポキシ樹脂を含む、請求項1〜10のいずれか一項に記載のエポキシ樹脂組成物。
- EEWが500〜1500g/eqであり全エポキシ樹脂100重量部当たり10〜40重量部の量で存在する第1のビスフェノール型エポキシ樹脂を含む、請求項11に記載のエポキシ樹脂組成物。
- EEWが150〜200g/eqである第2のビスフェノール型エポキシ樹脂をさらに含む、請求項11に記載のエポキシ樹脂組成物。
- 熱可塑性樹脂をさらに含む、請求項1〜13のいずれか一項に記載のエポキシ樹脂組成物。
- 請求項1〜14のいずれか一項に記載のエポキシ樹脂組成物からなるプリプレグ。
- 請求項15に記載のプリプレグを硬化させてなる繊維強化プラスチック材料。
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CN108473660B (zh) * | 2016-01-19 | 2021-06-25 | 三菱化学株式会社 | 环氧树脂组合物、纤维增强复合材料用预浸料及纤维增强复合材料 |
WO2018005045A1 (en) * | 2016-06-27 | 2018-01-04 | Dow Global Technologies Llc | Storage stable epoxy prepregs from dicyandiamide solutions and methods for making the same |
KR102428285B1 (ko) * | 2016-09-13 | 2022-08-08 | 주식회사 테크위드 | 자전거 림을 위한 고온 수지 조성물 및 이를 이용한 자전거 림 |
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WO2019098028A1 (ja) * | 2017-11-16 | 2019-05-23 | 三菱ケミカル株式会社 | 熱硬化性樹脂組成物、プリプレグ、ならびに繊維強化複合材料およびその製造方法 |
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