JP2016138162A - 架橋性組成物、硬化物の製造方法、および硬化物 - Google Patents
架橋性組成物、硬化物の製造方法、および硬化物 Download PDFInfo
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- JP2016138162A JP2016138162A JP2015012105A JP2015012105A JP2016138162A JP 2016138162 A JP2016138162 A JP 2016138162A JP 2015012105 A JP2015012105 A JP 2015012105A JP 2015012105 A JP2015012105 A JP 2015012105A JP 2016138162 A JP2016138162 A JP 2016138162A
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- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical class OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])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
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- MLVWCBYTEFCFSG-UHFFFAOYSA-L zinc;dithiocyanate Chemical compound [Zn+2].[S-]C#N.[S-]C#N MLVWCBYTEFCFSG-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
Description
nは2〜6の整数であり、
R1およびR2は、それぞれ独立に、水素原子、脂肪族炭化水素基、脂環式炭化水素基、芳香族炭化水素基、一般式(2)で表される基、または一般式(3)で表される基を表し、n個あるR1およびn個あるR2はそれぞれ、同一でも異なっていても良い。また、n個あるR1のうち少なくとも1つは一般式(2)で表される基、n個あるR2のうち少なくとも1つは一般式(3)で表される基である。)
R7は一般式(4)で表される基、‐CH2‐Y、または‐CO‐Yを表し、Yは脂環式エポキシ基を表す。)
る。
攪拌機、温度計、滴下装置、ディーンスターク管、還流冷却器、ガス導入管を備えた反応容器に、アジピン酸(ヘキサン二酸)146部、ジエタノールアミン105部、水酸化カリウム2部、トルエン200部を入れ、ディーンスターク管にはトルエンを満たし、窒素を吹き込みながら加熱還流させ、共沸によって生成する水を除去した。4時間後、トルエンをすべて除去し、1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃まで降温した後、得られた均一な淡黄色透明の溶液を取り出した。
窒素雰囲気下、攪拌機、温度計、ディーンスターク管、還流冷却器、減圧装置を備えた反応容器に、アジピン酸ジメチル(ヘキサン二酸ジメチル)174部、ジエタノールアミン105部、ナトリウムメトキシド3部を入れ、常圧状態で内温が90℃になるまで加熱攪拌した。内温が90℃に達したら、500hPaの減圧状態で2時間加熱攪拌し、生成するメタノールを留去しながら反応を進行させた。2時間後、200hPaの減圧状態でさらに1時間加熱攪拌し、残存するメタノールを全て留去した。1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃まで降温した後、得られた均一な淡黄色透明の溶液を取り出した。
窒素雰囲気下、攪拌機、温度計、ディーンスターク管、還流冷却器、減圧装置を備えた反応容器に、アジピン酸ジメチル(ヘキサン二酸ジメチル)174部、ジエタノールアミン105部、1,8−ジアザビシクロ[5.4.0]−7−ウンデセン8部を入れ、常圧状態で内温が90℃になるまで加熱攪拌した。内温が90℃に達したら、500hPaの減圧状態で2時間加熱攪拌し、生成するメタノールを留去しながら反応を進行させた。2時間後、200hPaの減圧状態でさらに1時間加熱攪拌し、残存するメタノールを全て留去した。1H−NMR測定、IR測定を行って目的物が生成していることを確認した。50℃まで降温した後、得られた均一な淡黄色透明の溶液を取り出した。
窒素雰囲気下、攪拌機、温度計、ディーンスターク管、還流冷却器、減圧装置を備えた反応容器に、化合物1中間体320部、エピクロロヒドリン462部、n−ブタノール800部、テトラエチルベンジルアンモニウムクロライド2部を仕込み、常圧状態で内温が65℃になるまで加熱攪拌した。内温が65℃に達したら、共沸する圧力まで減圧して、49%水酸化ナトリウム水溶液90部を5時間かけて滴下した。その後、同条件で0.5時間撹拌を続けた。ディーンスターク管にはn−ブタノールを満たし、縮合により生成する水をn−ブタノールと共沸させることで留出させ、n−ブタノールは反応器に戻るようにした。その後、未反応のエピクロロヒドリンを減圧蒸留によって留去させた。得られた溶液に10%水酸化ナトリウム水溶液50部を添加して80℃で2時間反応させた後に洗浄液のpHが中性となるまで水900部で水洗を3回繰り返した。次いで共沸によって系内を脱水し、溶媒を減圧下で留去し、化合物1を376部得た。1H−NMR測定を行って目的物が生成していることを確認した。
窒素雰囲気下、攪拌機、温度計、ディーンスターク管、還流冷却器、減圧装置を備えた反応容器に、化合物1中間体320部、3−シクロヘキセン−1−メタノール112部、濃硫酸1部、キシレン432部を仕込み、窒素ガスを吹き込みながら120℃に加熱した。ディーンスターク管にはキシレンを満たし、縮合により生成する水をキシレンと共沸させることで留出させ、キシレンは反応器に戻るようにした。8時間後残ったキシレンをすべて留去し、トルエン300部を加え、トルエン溶液を飽和炭酸水素ナトリウム水溶液で洗浄した。この溶液にm−クロロ過安息香酸(純度65%)を780部加え、8時間室温で撹拌した。この溶液を10%亜硫酸ナトリウム水溶液、飽和炭酸水素ナトリウム水溶液、水で洗浄したのち、硫酸ナトリウムで乾燥した。濾過後トルエンを留去し、化合物2を430部得た。1H−NMR測定を行って目的物が生成していることを確認した。
窒素雰囲気下、攪拌機、温度計、ディーンスターク管、還流冷却器、減圧装置を備えた反応容器に、化合物1中間体320部、3−シクロヘキセン−1−カルボン酸126部、キシレン446部を仕込み、窒素ガスを吹き込みながら200℃に加熱した。ディーンスターク管にはキシレンを満たし、縮合により生成する水をキシレンと共沸させることで留出させ、キシレンは反応器に戻るようにした。8時間後残ったキシレンをすべて留去し、トルエン350部を加え、トルエン溶液を飽和炭酸水素ナトリウム水溶液で洗浄した。この溶液にm−クロロ過安息香酸(純度65%)を807部加え、8時間室温で撹拌した。この溶液を10%亜硫酸ナトリウム水溶液、飽和炭酸水素ナトリウム水溶液、水で洗浄したのち、硫酸ナトリウムで乾燥した。濾過後トルエンを留去し、化合物3を444部得た。1H−NMR測定を行って目的物が生成していることを確認した。
攪拌機、温度計、滴下装置、還流冷却器、ガス導入管を備えた反応容器にメチルエチルケトンを500部入れ、窒素を吹き込みながら70℃で1時間加熱攪拌した。その後、ブチルアクリレート374.4部、アクリル酸25.6部、2,2’−アゾビス(2,4−ジメチルバレロニトリル)11.4部、メチルエチルケトン100部を混合した溶液を滴下装置から2時間かけて滴下した。さらに70℃で2時間反応させ、2,2’−アゾビス(2,4−ジメチルバレロニトリル)1.1部とメチルエチルケトン10部からなる溶液を加え、さらに1時間攪拌した。できた樹脂溶液は固形分NV=39.1%、数平均分子量Mn=16,000、重量平均分子量Mw=34,000、酸価AV=50.2mgKOH/gであった。
攪拌機、温度計、還流冷却器、ガス導入管を備えた反応容器に、クラレポリオールP−1010(クラレ(株)社製 水酸基価112mgKOH/g)を1002部、ジメチロールブタン酸237部、イソホロンジイソシアネート576部、メチルエチルケトン1815部を仕込み、窒素気流下で80℃まで昇温した。その後ジブチル錫ジラウレートを0.1部加えた。4時間反応させたのち、IRを測定し2270cm-1付近のイソシアネート由来のピークが消失したことを確認した。できた樹脂溶液は固形分NV=39.9%、数平均分子量Mn=23,000、重量平均分子量Mw=51,000、酸価AV=50.0mgKOH/gであった。
化合物1を10部、溶剤60部、樹脂合成例1で合成した樹脂溶液から溶剤を取り除いた樹脂40部を混合した。溶剤としてメチルエチルケトン(MEK)、酢酸エチル、トルエンを用いた。このときに均一な液体として得られたものは○、濁りのあるものは△、固体が沈殿した場合は×とした。
化合物1の代わりに、化合物2〜62を使用した以外は、実施例1と同様に試験を行った。
化合物1の代わりに、化合物A(Primid XL−552(エムスケミー社製のβ−ヒドロキシアルキルアミド))を用いた以外は、実施例1と同様に試験を行った。
化合物1の代わりに、化合物Bを用いた以外は、実施例1と同様に試験を行った。
化合物1の代わりに、化合物Cを用いた以外は、実施例1と同様に試験を行った。
化合物1の代わりに、化合物Bと化合物Cの重量比1:1の混合物を用いた以外は、実施例1と同様に試験を行った。
化合物1を用いた架橋性組成物の硬化性試験(1)、保存安定性試験(1)、および硬化膜強度試験(1)を行った。
に試験片を挟み込み、一定の周波数(1Hz)で、温度を10℃/分で昇温させ、−50〜250℃での測定を行い、その30〜120℃での貯蔵弾性率を決定した。試験片は、厚みが1.0mmのものを用いた。30〜120℃における貯蔵弾性率が105Pa未満の硬化膜を×、105Pa以上106Pa未満の硬化膜を△、106Pa以上の硬化膜を○とした。なお、粘弾性測定はすべて、TAインストゥルメンツ社製のARESIIIを用いて行った。
化合物1の代わりに、化合物2〜62を使用した以外は、実施例63と同様に試験を行った。
化合物1の代わりに、化合物A〜Cを用いた以外は、実施例63と同様に試験を行った。
化合物1の代わりに、化合物Bと化合物Cの重量比1:1の混合物を用いた以外は、実施例63と同様に試験を行った。
化合物1を用いた架橋性組成物の硬化性試験(2)、保存安定性試験(2)、および硬化膜強度試験(2)を行った。
に試験片を挟み込み、一定の周波数(1Hz)で、温度を10℃/分で昇温させ、−50〜250℃での測定を行い、その30〜120℃での貯蔵弾性率を決定した。試験片は、厚みが1.0mmのものを用いた。30〜120℃における貯蔵弾性率が105Pa未満の硬化膜を×、105Pa以上106Pa未満の硬化膜を△、106Pa以上の硬化膜を○とした。なお、粘弾性測定はすべて、TAインストゥルメンツ社製のARESIIIを用いて行った。
化合物1の代わりに、化合物2〜42を使用した以外は、実施例125と同様に試験を行った。
化合物1の代わりに、化合物A〜Cを用いた以外は、実施例125と同様に試験を行った。
化合物1の代わりに、化合物Bと化合物Cの重量比1:1の混合物を用いた以外は、実施例125と同様に試験を行った。
Claims (5)
- 下記一般式(1)で表される化合物と、有機溶剤と、カルボキシ基を有する樹脂とからなる架橋性組成物。
一般式(1)
nは2〜6の整数であり、
R1およびR2は、それぞれ独立に、水素原子、脂肪族炭化水素基、脂環式炭化水素基、芳香族炭化水素基、一般式(2)で表される基、または一般式(3)で表される基を表し、n個あるR1およびn個あるR2はそれぞれ、同一でも異なっていても良い。また、n個あるR1のうち少なくとも1つは一般式(2)で表される基、n個あるR2のうち少なくとも1つは一般式(3)で表される基である。)
一般式(2)
一般式(3)
R7は一般式(4)で表される基、‐CH2‐Y、または‐CO‐Yを表し、Yは脂環式エポキシ基を表す。)
一般式(4)
- Xが炭素数6〜20の直鎖の脂肪族炭化水素基であることを特徴とする請求項1記載の架橋性組成物。
- Xが炭素数6〜12の直鎖の脂肪族炭化水素基であることを特徴とする請求項1または2記載の架橋性組成物。
- 請求項1〜3いずれか記載の架橋性組成物を加熱してなる硬化物の製造方法。
- 請求項4記載の製造方法で得られる硬化物。
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