JP6947712B2 - 珪素含有化合物、ウレタン樹脂、伸縮性膜、及びその形成方法 - Google Patents
珪素含有化合物、ウレタン樹脂、伸縮性膜、及びその形成方法 Download PDFInfo
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- JP6947712B2 JP6947712B2 JP2018188896A JP2018188896A JP6947712B2 JP 6947712 B2 JP6947712 B2 JP 6947712B2 JP 2018188896 A JP2018188896 A JP 2018188896A JP 2018188896 A JP2018188896 A JP 2018188896A JP 6947712 B2 JP6947712 B2 JP 6947712B2
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Description
下記一般式(1)で示される珪素含有化合物と、イソシアネート基を有する化合物とを混合し、該混合物を製膜し、加熱によって硬化させる伸縮性膜の形成方法を提供する。
下記一般式(4)で示される、末端に(メタ)アクリレート基を有する化合物を製膜し、加熱及び/又は光照射によって硬化させる伸縮性膜の形成方法を提供する。
下記一般式(1)で示される珪素含有化合物と、イソシアネート基を有する化合物とを混合し、該混合物を製膜し、加熱によって硬化させる伸縮性膜の形成方法である。
本発明の珪素含有化合物は、下記一般式(1)で示されるものである。
本発明のウレタン樹脂の作製方法としては、特に限定されないが、上述した本発明の珪素含有化合物を原料とし、この珪素含有化合物とイソシアネート基を有する化合物(イソシアネート化合物)と反応させて作製することが好ましい。
また、本発明では、前述の本発明のウレタン樹脂を含有する伸縮性膜を提供する。
本発明では、伸縮性膜を形成する方法であって、
下記一般式(1)で示される珪素含有化合物と、イソシアネート基を有する化合物とを混合し、該混合物を製膜し、加熱によって硬化させる伸縮性膜の形成方法を提供する。
下記一般式(4)で示される、末端に(メタ)アクリレート基を有する化合物を製膜し、加熱及び/又は光照射によって硬化させる伸縮性膜の形成方法を提供する。
下記式(5)に記載の反応式に示す反応を行った。
1L2口フラスコにmeso―エリスリトール50g、DMF500g、トリエチルアミン104gとN,N―ジメチルアミノピリジン0.5gを仕込み、窒素雰囲気下、室温で撹拌した。続いて、氷冷下でトリチルクロライドを加えた後、室温で3時間撹拌した。反応液を2Lビーカーに移し、水1Lを加えて撹拌した後、析出物をブフナーロートでろ取した。得られた粉末を2Lビーカーに戻し、酢酸エチル500mLとヘキサン500mLで3回洗浄した後、真空乾燥することで以下の性質のジオール(5−I)を207g得た。
黄白色紛体
1H−NMR(500MHz,DMSO−d6):δ=7.45−7.10(30H,m),4.75(2H,s),3.66−3.61(2H,m),3.00−2.93(4H,m)
2L2口フラスコにジオール(5−I)100gとDMF700gを仕込み、窒素雰囲気下、40℃で撹拌、溶解させた後、氷浴を用いて溶液を冷却した。続いて、水素化ナトリウム24gを加え、2時間撹拌した後、アリルブロマイド44gを滴下した。室温で2.5時間撹拌した後、反応液を氷浴で冷却し、水700gを加えた。続いて、生じた析出物をブフナーロートでろ取し、水1000gで2回、THF150gとヘキサン400gで1回洗浄した後、真空乾燥することで以下の性質のジアリル化合物(5−II)を100g得た。
黄白色紛体
1H−NMR(500MHz,THF−d8):δ=7.50−7.40(12H,m),7.26−7.14(18H,m),5.82−5.73(2H,m),5.13(2H,d),5.01(2H,d),4.10−4.04(2H,m),3.94−3.88(2H,m),3.66−3.60(2H,m),3.36(2H,d),3.19(2H,d)
2L1口フラスコにジアリル化合物(5−II)99.7gとギ酸300gを仕込み、窒素雰囲気下、60℃で1日撹拌した。イソプロピルエーテル300gを添加して、更に1日、60℃で撹拌した後、室温に戻し、メタノール300gと水300gを加え、生じた不溶分を除去した。ろ液を濃縮して得られた残渣をシリカゲルカラムクロマトグラフィで精製することで以下の性質のジアリルジオール(5−III)を28.4g得た。
黄白色紛体
1H−NMR(500MHz,CDCL3):δ=5.91−5.82(2H,m),5.27(2H,d),5.19(2H,d),4.58(2H,d)、4.24(2H,d),4.18−4.12(2H,m),4.06−4.00(2H,m),3.68−3.64(2H,m)
300mL3口フラスコにジアリルジオール(5−III)28.0g、トルエン43.8gとPL50N0.1gを仕込み、窒素雰囲気下、55℃まで加温した。続いて100mL滴下漏斗を用いてへプタメチルトリシロキサン61.7gを1時間半かけて滴下した。滴下終了後7時間撹拌を行った後、室温まで戻し、活性炭1gを加えた。2時間撹拌後、セライト濾過し、得られた溶液を減圧濃縮することで以下の性質のシリコーンペンダントジオール化合物1(5−IV)を67.1g得た。
黄色オイル
1H−NMR(500MHz,CDCl3):δ=4.59(2H,d),4.23(2H,d),3.61−3.54(4H,m),3.39−3.34(2H,m),1.57−1.51(4H,m),0.45−0.39(4H,m),0.08(36H,s),0.01(6H,s)
使用したジオール以外は、式(5)に記載の反応式に示すヒドロシリル化反応と同様に、シリコーンペンダントジオール化合物2〜4、比較シリコーンペンダントジオール化合物1を合成した。
光ラジカル発生剤1:4,4’−ジメトキシベンジル
光ラジカル発生剤2:2,2−ジメトキシ−2−フェニルアセトフェノン
光ラジカル発生剤3:(±)−カンファーキノン
熱ラジカル発生剤1:2,2’−アゾビス(2−メチルプロピオン酸)ジメチル
有機溶剤:プロピレングリコールモノメチルエーテルアセテート(PGMEA)
アルキル基やアリール基を有するモノマー:イソボロニルアクリレート
表1に記載の組成で、シリコーンペンダントジオール化合物、イソシアネート化合物、ヒドロキシ化合物、添加剤を混合、脱泡し、伸縮性膜形成用組成物(伸縮性膜材料1−1〜1−6、比較伸縮性膜材料1−1)を調製した。脱気後、ポリエチレン基板上に、伸縮性膜材料1−1〜1−6、比較伸縮性膜材料1−1をバーコート法で塗布し、130℃で20分間ベークして基板上に伸縮性膜(Film1−1〜1−6、比較Film1−1)を作製した。また、伸縮性膜形成用組成物におけるヒドロキシ基とイソシアネート基のモル数の比を表1に併せて示す。
硬化後の伸縮性膜における膜厚、及び表面の水の接触角を測定した。また、伸縮性膜表面の水の接触角を測定した後に、伸縮性膜を基板から剥がし、JIS K 6251に準じた方法で伸縮率と強度を測定した。結果を表3に示す。
5…粘着部、 6,6’…伸縮性膜、 7…基板、 8…布。
Claims (9)
- 請求項3又は請求項4に記載のウレタン樹脂を含有することを特徴とする伸縮性膜。
- 前記伸縮性膜が、JIS K 6251に規定される引っ張り試験で伸縮率が40〜500%のものであることを特徴とする請求項5に記載の伸縮性膜。
- 前記伸縮性膜が、伸縮性を有する導電性配線に接触する膜として用いられるものであることを特徴とする請求項5又は請求項6に記載の伸縮性膜。
- 伸縮性膜を形成する方法であって、
下記一般式(4)で示される、末端に(メタ)アクリレート基を有する化合物を製膜し、加熱及び/又は光照射によって硬化させることを特徴とする伸縮性膜の形成方法。
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