JP2013510928A - ポリマー組成物並びにその製造方法及び物品 - Google Patents
ポリマー組成物並びにその製造方法及び物品 Download PDFInfo
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- JP2013510928A JP2013510928A JP2012538920A JP2012538920A JP2013510928A JP 2013510928 A JP2013510928 A JP 2013510928A JP 2012538920 A JP2012538920 A JP 2012538920A JP 2012538920 A JP2012538920 A JP 2012538920A JP 2013510928 A JP2013510928 A JP 2013510928A
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Abstract
Description
「架橋」は、物質の弾性率を高めるために、予め生成した2本のポリマー鎖を、化学結合又は化学基を使用して連結させることを指す;
「硬化部位」は、架橋に使用することができる官能基を指す;
「共重合された」は、一緒に重合されてポリマー主鎖を形成するモノマーを指す。
X−R−(Z)n (I)
式中、Xは上記のような第一官能基であり、Rは多官能性有機基であり、かつZすなわち上記のような第二官能基は−N3又は−C≡C−R’から選択され、ここでR’は水素又は単官能性有機基であり、かつnは1〜約10である。
OCNC6H7(CH3)3CH2NHCOOCH2C≡CH、CH3C2H3NC(O)NHC6H7(CH3)3CH2HNCOOCH2C≡CH、OCNC6H7(CH3)3CH2NHCOOCH2CH2N3、
CH3C2H3NC(O)NHC6H7(CH3)3CH2HNCOOCH2CH2N3、及びこれらの組み合わせが挙げられる。
−X’−R−(Z)n (II)
式中、X’は式(I)の反応した第一官能基であり、式(II)中のR、Z、及びnは、式(I)中のR、Z及びnと同様の意味を有する。
−C(O)O CH2CHCH3NC(O)NHC6H7(CH3)3CH2HNCOOCH2C≡CH、
−C(O)O CH2CHCH3NC(O)NHC6H7(CH3)3CH2HNCOOCH2CH2N3、
−OC(O)NHC6H7(CH3)3CH2NHC(O)OCH2C≡CH、
−OC(O)NHC6H7(CH3)3CH2NHC(O)OCH2CH2N3、及びこれらの組み合わせが挙げられる。
流量計使用方法−応力ひずみ制御レオメーターAR2000(TA Instruments(New Castle,DE))を使用して、サンプルを2枚の20mm平行プレート間に配置した。ボトムプレートを160℃に加熱し、実験の持続時間にわたって温度を25℃〜125℃に掃引した。上のプレートは周波数1ヘルツで振動させ、2mmの1%のひずみを与えて、試験サンプルの弾性率を得た。次いで振動及び弾性率測定を、5℃〜145℃の温度範囲にわたって温度を20℃ずつ上昇させ繰り返した。振動及び弾性率の測定の前に、サンプル温度を1分にわたって平衡化させた。次いでデータをパスカル(Pa)対温度(℃)の弾性率(G’)として保存し、log G’対温度としてプロットした。
アジド−イソシアネート−イソホロンジイソシアネート(Bayer(Pittsburgh,PA))22.2g及び2−アジドエタノール(米国仮出願特許第12/271,222号(Crandallら)に記載のように調製)8.7gのトルエン(100g)溶液に、ジブチル錫ジラウレート0.05gを添加した。発熱反応が観察され、混合物の温度は45℃に上昇した。混合物を更に30分にわたって65℃に加熱し、次いで室温に放冷した。構造をFT−IR分光法で確認した。ピークは次のように記録された:2267/cm、イソシアネート;2104/cm、アジド基;及び1708/cm、ウレタンカルボニル。
比較例A
IOA/AA 8.0グラムを用いてサンプルを製造した。ライナー(乾燥させたサンプルを剥がすのに十分低い剥離力を有する、ポリコーティングした紙ライナー)上にサンプルをコーティングし、室温で24時間にわたって風乾させた。
IOA/AA 8.0gと、等部のアジド−アジリジン(0.6g)及びプロパルギル−アジリジン(0.6g)とを混合することでサンプルを製造した。ライナー(乾燥させたサンプルを剥がすのに十分低い剥離力を有する、ポリコーティングした紙ライナー)上にサンプルをコーティングし、室温で24時間にわたって風乾させた。
IOA/AA(25g)を等部のアジド−アジリジン(0.3g)及びプロパルギル−アジリジン(0.3g)と混合した。酢酸エチル(6.4g)を加え固形濃度を20%に下げ、これを20分にわたって混合した。標的乾燥重量1ミル(25.4マイクロメートル)で、2ミル(50.8マイクロメートル)のポリ(エチレンテレフタレート)上に、溶液をコーティングした。3種のサンプル(サンプル1、サンプル2及びサンプル3)を作製し、65℃にて30分にわたって乾燥させた。次いでサンプル2を105℃にて30分にわたって加熱し、これに対しサンプル3を130℃にて30分にわたって加熱した。3種のサンプルすべてを温度及び湿度の制御された室内(70°F(21.1℃)かつ相対湿度50%)に一晩置いて平衡化させた。サンプルを切り出し、剥離接着力及び静的せん断力について試験した。結果を表2に記す。
IOA/AA(25g)を等部のアジド−アジリジン(0.18g)及びプロパルギル−アジリジン(0.18g)と混合した。酢酸エチル(6.4g)を加え固形濃度を20%に下げ、これを20分にわたって混合した。標的乾燥重量1ミル(25.4マイクロメートル)を有する、2ミル(50.8マイクロメートル)のポリ(エチレンテレフタレート)上に、溶液をコーティングした。3種のサンプル(サンプル1、サンプル2及びサンプル3)を作製し、65℃にて30分にわたって乾燥させた。次いでサンプル2を105℃にて30分にわたって加熱し、これに対しサンプル3を130℃にて30分にわたって加熱した。3種のサンプルすべてを温度及び湿度の制御された室内(73.4°F(23℃)かつ相対湿度50%)に一晩置いて平衡化させた。サンプルを切り出し、剥離接着力及び静的せん断力について試験した。結果を表3に報告する。
比較例Bは、上記実施例3のように調製したが、アジド−アジリジン又はプロパルギル−アジリジンは全く加えなかった。
トルエンによりポリエステルポリオール(9g)を固形分75%に希釈した。固形分50%のプロパルギル−アジリジン溶液及び固形分50%のアジド−アジリジン溶液をトルエンを溶媒にして調製し、下表3に従ってポリエステルポリオール溶液と混合した。サンプルは15分にわたって混合し、次いで105℃にて2〜4時間にわたって溶媒を乾燥させた。次いでサンプルを130℃にて2〜4時間にわたって硬化させた。下表3は、得られたサンプルの物理特性の観察を示す。図2は、実施例6〜8についての、log G’対温度のグラフを示す。
ポリウレタン(10g)をメチルエチルケトンで固形分40%に希釈した。固形分50%のプロパルギル−アジリジン溶液及び固形分50%のアジド−アジリジン溶液をメチルエチルケトンを溶媒にして調製し、下表3に従ってポリウレタン溶液と混合した。サンプルは15分にわたって混合し、次いで105℃にて2〜4時間にわたって溶媒を乾燥させた。次いでサンプルを130℃にて2〜4時間にわたって硬化させた。下表3は、得られたサンプルの物理特性の観察を示す。
ポリウレタン(10g)をメチルエチルケトンで固形分40%に希釈した。サンプルは15分にわたって混合し、次いで105℃にて2〜4時間にわたって溶媒を乾燥させた。下表3は、得られたサンプルの観察された物理特性を示す。図3は、実施例9〜11及び比較例Cについての、log G’対温度のグラフを示す。
(実施例12〜14)
IOA/HEMA、並びにプロパルギル−イソシアネート及びアジド−イソシアネートの24%(重量/重量)溶液をトルエンを溶媒にして調製し、下表4に従って混合してさまざまな程度の架橋を生成した。サンプルを周囲温度にて5分にわたって混合し、105℃にて30分にわたって溶媒を乾燥させた。次いでサンプルを130℃にて2時間にわたって硬化させた。図4は、各サンプルについてのlog G’対温度を示す。
比較例D
IOA/HEMAをメチルエチルケトンで希釈した。サンプルを5分にわたって混合し、次いで105℃にて30分にわたって溶媒を乾燥させた。次いでサンプルを130℃にて2時間にわたって硬化させた。図4は、実施例12〜14及び比較例Dについての、log G’対温度のグラフを示す。
ポリマー1:アクリロニトリル−ブタジエンコポリマー(9.5g)を酢酸エチルで固形分75%に希釈した。プロパルギル−アジリジン(3.47g、トルエン中50重量%)をアクリロニトリル−ブタジエンコポリマー溶液に添加し、周囲温度にて15分にわたって混合し、アルキン官能化アクリロニトリル−ブタジエンコポリマーを生成した。105℃にて2時間にわたって混合物から溶媒を乾燥させた。
アジド−アジリジン又はプロパリル−アジリジンを全く加えなかったことを除き、比較例Eを上記実施例15〜19に記載のように調製した。
Claims (24)
- 混合物であって、
(a)非自己架橋性ポリマー;並びに
(b)修飾化合物であって、
(i)前記非自己架橋性ポリマーと反応することができる第一官能基と
(ii)硬化剤により架橋することができる第二官能基と、を含む修飾化合物、を含み、
前記第一官能基は前記第二官能基とは異なる、混合物。 - 前記第一官能基が、アジリジンアミド、アジリジン尿素、イソシアネート、アルコール、エポキシ、アミン、スルフヒドリル、及びこれらの組み合わせから選択される、請求項1に記載の混合物。
- 前記第二官能基が、アルキン又はアジドから選択される、請求項1又は2に記載の混合物。
- 前記修飾化合物が:
CH3C2H3NC(O)NHC6H7(CH3)3CH2HNCOOCH2C≡CH、
CH3C2H3NC(O)NHC6H7(CH3)3CH2HNCOOCH2CH2N3、
OCNC6H7(CH3)3CH2NHCOOCH2C≡CH、
OCNC6H7(CH3)3CH2NHCOOCH2CH2N3、又はこれらの組み合わせのうちの少なくとも1つから選択される、請求項1〜3のいずれか一項に記載の混合物。 - 前記非自己架橋性ポリマーが、ヒドロキシル、アミノ、カルボキシ、エポキシ、二重結合、ケトン、アルデヒド、又はこれらの非自己反応性の組み合わせのうちの少なくとも1つから選択される反応部位を含む、請求項1〜4のいずれか一項に記載の混合物。
- 前記非自己架橋性ポリマーが、(メタ)アクリレート、ポリウレタン、ポリエステル、ポリシロキサン、ポリオレフィン、ポリエーテル、ポリアミド、又はこれらの組み合わせのうちの少なくとも1つから選択される、請求項1〜5のいずれか一項に記載の混合物。
- 硬化剤を更に含み、該硬化剤は第三官能基を含み、該第三官能基は前記第二官能基と反応して前記硬化性ポリマー組成物を架橋することができる、請求項1〜6のいずれか一項に記載の混合物。
- 前記第二官能基及び前記第三官能基がアジド−アルキン架橋を形成する、請求項6に記載の混合物。
- 前記硬化剤が小分子である、請求項7又は8に記載の混合物。
- 前記硬化剤が第二ポリマーである、請求項7〜9のいずれか一項に記載の混合物。
- 前記第二ポリマーが、前記非自己架橋性ポリマーとは異なる、請求項10に記載の混合物。
- 官能基が活性な化合物を更に含み、該官能基が活性な化合物が、官能部、及び少なくとも1つのペンダントアルキン基又はペンダントアジド基を含む、請求項1〜11のいずれか一項に記載の混合物。
- 前記官能部が染料、光安定剤、又はイメージング分子から選択される、請求項12に記載の混合物。
- 請求項1に記載の反応生成物、及び硬化剤を含む、硬化性ポリマー組成物。
- −C(O)O CH2CHCH3NC(O)NHC6H7(CH3)3CH2HNCOOCH2C≡CH、
−C(O)O CH2CHCH3NC(O)NHC6H7(CH3)3CH2HNCOOCH2CH2N3、
−OC(O)NHC6H7(CH3)3CH2NHC(O)OCH2C≡CH、
−OC(O)NHC6H7(CH3)3CH2NHC(O)OCH2CH2N3、及びこれらの組み合わせ、のうちの少なくとも1つから選択される置換基を含む非自己架橋性ポリマーを含む、硬化性ポリマー組成物。 - 前記硬化性ポリマー組成物が接着剤及びコーティングのうちの少なくとも1つである、請求項14又は15に記載の硬化性ポリマー組成物。
- 請求項14に記載の硬化性ポリマー組成物を含む物品であって、該物品が充填ポリマー、強化複合材料、プライマー又は構造物品である、物品。
- X−R−(Z)n
のうちの少なくとも1つを含む組成物であって、式中、Xは、アジリジンアミド,アジリジン尿素、イソシアネート、アルコール、アミン、エポキシ、又はスルフヒドリルから選択され、Rは多官能性有機基であり、かつZは−N3又は−C≡C−R’から選択され、式中、R’は水素又は単官能性有機基であり、かつnは1〜約10である、組成物。 - 前記組成物が、
CH3C2H3NC(O)NHC6H7(CH3)3CH2HNCOOCH2C≡CH、
CH3C2H3NC(O)NHC6H7(CH3)3CH2HNCOOCH2CH2N3、
OCNC6H7(CH3)3CH2NHCOOCH2C≡CH、及びOCNC6H7(CH3)3CH2NHCOOCH2CH2N3のうちの少なくとも1つから選択される、請求項18に記載の組成物。 - (a)請求項1〜13のいずれか一項に記載の混合物を提供することと、
(b)前記非自己架橋性ポリマーと前記修飾化合物を反応させて官能化ポリマーを得ることと、
(c)前記硬化剤により前記官能化ポリマーを架橋させることと、を含む、方法。 - 前記反応させること及び架橋させることが熱により活性化される、請求項20に記載の方法。
- 前記反応温度が前記架橋温度未満である、請求項21に記載の方法。
- 前記反応温度が約0℃〜100℃である、請求項21又は22に記載の方法。
- 前記架橋温度が約50℃〜200℃である、請求項21又は22に記載の方法。
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2010
- 2010-11-10 JP JP2012538920A patent/JP5837502B2/ja not_active Expired - Fee Related
- 2010-11-10 WO PCT/US2010/056104 patent/WO2011059994A2/en active Application Filing
- 2010-11-10 EP EP10830608.5A patent/EP2499201B1/en not_active Not-in-force
- 2010-11-10 US US12/943,116 patent/US8703877B2/en not_active Expired - Fee Related
- 2010-11-10 CN CN201080048411.8A patent/CN102597120B/zh not_active Expired - Fee Related
- 2010-11-10 KR KR1020127015070A patent/KR20120115262A/ko not_active Application Discontinuation
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2014
- 2014-03-05 US US14/197,731 patent/US20140187722A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
---|---|
EP2499201B1 (en) | 2017-05-10 |
US20110112254A1 (en) | 2011-05-12 |
US8703877B2 (en) | 2014-04-22 |
WO2011059994A3 (en) | 2011-09-09 |
CN102597120A (zh) | 2012-07-18 |
WO2011059994A2 (en) | 2011-05-19 |
US20160369069A1 (en) | 2016-12-22 |
JP5837502B2 (ja) | 2015-12-24 |
US20140187722A1 (en) | 2014-07-03 |
EP2499201A2 (en) | 2012-09-19 |
CN102597120B (zh) | 2015-05-27 |
KR20120115262A (ko) | 2012-10-17 |
EP2499201A4 (en) | 2014-08-13 |
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