JP5348501B2 - ポリアミドアミン硬化剤、エポキシ樹脂組成物及びその硬化物 - Google Patents
ポリアミドアミン硬化剤、エポキシ樹脂組成物及びその硬化物 Download PDFInfo
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- JP5348501B2 JP5348501B2 JP2010026416A JP2010026416A JP5348501B2 JP 5348501 B2 JP5348501 B2 JP 5348501B2 JP 2010026416 A JP2010026416 A JP 2010026416A JP 2010026416 A JP2010026416 A JP 2010026416A JP 5348501 B2 JP5348501 B2 JP 5348501B2
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- epoxy resin
- curing agent
- acid
- monocarboxylic acid
- resin composition
- Prior art date
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
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- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
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Description
NH2(C2H4NH)nH・・・(1)
〔前記nは1以上である。〕
温度計、攪拌装置および脱水縮合用冷却管を備えた2L容器にテトラエチレンペンタミン(TEPA)100g、トール油脂肪酸(TOFA)110g(0.38モル)、安息香酸12g(0.1モル)を加えて攪拌下150℃に昇温した。150℃で1時間保持し、その後260℃まで3時間かけて昇温し、260℃で5時間保持した。その後生成した水を留去させ、活性水素当量が77、粘度(B型回転粘度計、以下同様。)が300mPa・sである目的のポリアミドアミン樹脂(A1)を得た。尚、トール油脂肪酸の分子量は290とした(以下同様。)。
温度計、攪拌装置および脱水縮合用冷却管を備えた2L容器にテトラエチレンペンタミン(TEPA)100g、トール油脂肪酸(TOFA)64g(0.22モル)、安息香酸12g(0.1モル)を加えて攪拌下150℃に昇温した。150℃で1時間保持し、その後260℃まで3時間かけて昇温し、260℃で5時間保持した。その後生成した水を留去させ、活性水素当量が56、粘度が200mPa・sである目的のポリアミドアミン樹脂(A2)を得た。
温度計、攪拌装置および脱水縮合用冷却管を備えた2L容器にテトラエチレンペンタミン(TEPA)100g、トール油脂肪酸(TOFA)168g(0.58モル)、安息香酸12g(0.1モル)を加えて攪拌下150℃に昇温した。150℃で1時間保持し、その後260℃まで3時間かけて昇温し、260℃で5時間保持した。その後生成した水を留去させ、活性水素当量が148、粘度が1000mPa・sである目的のポリアミドアミン樹脂(A3)を得た。
温度計、攪拌装置および脱水縮合用冷却管を備えた2L容器にヘキサエチレンヘプタミン100g、トール油脂肪酸(TOFA)73g(0.25モル)、安息香酸8g(0.066モル)を加えて攪拌下150℃に昇温した。150℃で1時間保持し、その後260℃まで3時間かけて昇温し、260℃で5時間保持した。その後生成した水を留去させ、活性水素当量が70、粘度が500mPa・sである目的のポリアミドアミン樹脂(A4)を得た。
温度計、攪拌装置および脱水縮合用冷却管を備えた2L容器にアミノエチルピペラジン(AEP)47部、テトラエチレンペンタミン(TEPA)352部にトール油脂肪酸(TOFA)461部、安息香酸76部、テレフタル酸64部を加えて攪拌下150℃に昇温した。150℃で1時間保持し、260℃まで3時間かけて昇温し、その後5時間保持した。その後生成する水を留去させ、活性水素当量が115、粘度が970mPa・sである比較対照用ポリアミドアミン樹脂(a1)を得た。
温度計、攪拌装置および脱水縮合用冷却管を備えた2L容器にテトラエチレンペンタミン(TEPA)100g、トール油脂肪酸(TOFA)44g(0.15モル)、安息香酸12g(0.1モル)を加えて攪拌下150℃に昇温した。150℃で1時間保持し、その後260℃まで3時間かけて昇温し、260℃で5時間保持した。その後生成した水を留去させ、活性水素当量が47、粘度が170mPa・sである目的の比較対照用ポリアミドアミン樹脂(a2)を得た。
温度計、攪拌装置および脱水縮合用冷却管を備えた2L容器にテトラエチレンペンタミン(TEPA)100g、トール油脂肪酸(TOFA)200g(0.69モル)、安息香酸12g(0.1モル)を加えて攪拌下150℃に昇温した。150℃で1時間保持し、その後260℃まで3時間かけて昇温し、260℃で5時間保持した。その後生成した水を留去させ、活性水素当量が140、粘度が1500mPa・sである比較対照用ポリアミドアミン樹脂(a3)を得た。
第1表に示す配合にてポリアミドアミン硬化剤(A)、エポキシ樹脂(B)を配合して本発明のエポキシ樹脂組成物(1)を調製した。得られたエポキシ樹脂組成物(1)の粘度を評価すると共に、下記条件にて組成物を硬化し、硬化物を得た。得られる硬化物の強度(引張強度、圧縮強度及び曲げ強度)を下記の基準に従って評価した。評価結果を第2表に示す。
第1表に示す配合にてポリアミドアミン硬化剤(A)と、エポキシ樹脂(B)を混合、脱泡後、速やかにB型回転粘度計を用いて測定した。
第1表に示す配合にてポリアミドアミン硬化剤(A)と、エポキシ樹脂(B)を混合、脱泡後、厚さ3mmになるようセットしたガラス板の隙間に試料を注入し、注型板を作成した。養生温度は25℃、養生期間は7日間とした。
前記硬化物を用いて、JIS−K6911(熱硬化性プラスチック一般試験方法)に準じて試験を行った。試験片の形状は切削状1号形とした。引張強度は最大点応力(Mpa)、伸び(%)及び弾性率(Mpa)を測定することにより評価した。
前記硬化物を用いて、JIS−K6911(熱硬化性プラスチック一般試験方法)に準じて試験を行った。試験片の形状は一辺20±0.5mmの立方体とした。最大点応力(Mpa)及び弾性率(Mpa)を測定することにより評価した。
前記硬化物を用いて、JIS−K7171(プラスチック−曲げ特性の求め方)に準じて試験を行った。試験片の形状は10mm×100mmの直方体とした。最大点応力(Mpa)及び弾性率(Mpa)を測定することにより評価した。
第1表に示す配合で行った以外は実施例1と同様にしてエポキシ樹脂組成物(2)〜(4)及び比較対照用エポキシ樹脂(1´)〜(3´)を得た。これらの組成物を用いて実施例1と同様の評価を行った。評価結果を第2表に示す。
EPILON850:DIC株式会社製のビスフェノールA型エポキシ樹脂。エポキシ当量190g/eq。
EPILON726:DIC株式会社製の1,6ヘキサンジオールジグリシジルエーテル。エポキシ当量155g/eq。
これらをEPILON850/EPILON726=80/20重量比にて混合品を調整し主剤とした。エポキシ当量182g/eq
第3表に示す配合にてポリアミドアミン硬化剤(A)、エポキシ樹脂(C)を配合して本発明のエポキシ樹脂組成物(5)〜8及び比較対照用エポキシ樹脂組成物(4´)〜6´を調製した。得られたエポキシ樹脂組成物の硬化物の外観を下記評価方法に評価した。評価結果を第4表に示す。
第2表に示す配合にてポリアミドアミン硬化剤(A)と、エポキシ樹脂(C)を混合、脱泡後、500μの厚みに塗布して硬化させ、7日後の外観を評価した。評価は、透明なものを○とし、濁りがあるものを△とした。養生温度は25℃、養生期間は7日間とした。
EPILON830:DIC株式会社製のビスフェノールF型エポキシ樹脂。エポキシ当量170g/eq。
Claims (8)
- ポリエチレンポリアミン(a1)と脂肪族モノカルボン酸(a2)と芳香族モノカルボン酸(a3)とを反応させて得られるポリアミドアミン硬化剤であり、脂肪族モノカルボン酸(a2)と芳香族モノカルボン酸(a3)とをモル比〔(a2)/(a3)〕で3/1〜5/1となる範囲で用いて得られることを特徴とするエポキシ樹脂用ポリアミドアミン硬化剤。
- 前記脂肪族モノカルボン酸(a2)がトール油脂肪酸であり、芳香族モノカルボン酸(a3)が安息香酸である請求項1記載のポリアミドアミン硬化剤。
- 前記ポリエチレンポリアミン(a1)がテトラエチレンペンタミンである請求項2記載のポリアミドアミン硬化剤。
- 前記ポリエチレンポリアミン(a1)がヘキサエチレンヘプタミンである請求項2記載のポリアミドアミン硬化剤。
- 請求項1〜4のいずれか1項記載のポリアミドアミン硬化剤(A)とエポキシ樹脂(B)とを含有することを特徴とするエポキシ樹脂組成物。
- 前記エポキシ樹脂(B)がビスフェノール型エポキシ樹脂(b1)、またはビスフェノール型エポキシ樹脂(b1)と反応性希釈剤(b2)との混合物である請求項5記載のエポキシ樹脂組成物。
- 接着剤用途である請求項6または7記載のエポキシ樹脂組成物。
- 請求項6〜7のいずれか1項記載のエポキシ樹脂組成物を硬化させてなることを特徴とする硬化物。
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