JP5837502B2 - 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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- JP5837502B2 JP5837502B2 JP2012538920A JP2012538920A JP5837502B2 JP 5837502 B2 JP5837502 B2 JP 5837502B2 JP 2012538920 A JP2012538920 A JP 2012538920A JP 2012538920 A JP2012538920 A JP 2012538920A JP 5837502 B2 JP5837502 B2 JP 5837502B2
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- Prior art keywords
- polymer
- alkyne
- azide
- crosslinking
- self
- Prior art date
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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。
本願発明に関連する発明の実施形態について以下に列挙する。
[実施形態1]
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。
[実施形態2]
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、実施形態1に記載の混合物。
[実施形態3]
前記第二官能基が、アルキン又はアジドから選択される、実施形態1又は2に記載の混合物。
[実施形態4]
前記修飾化合物が:
CH 3 C 2 H 3 NC(O)NHC 6 H 7 (CH 3 ) 3 CH 2 HNCOOCH 2 C≡CH、
CH 3 C 2 H 3 NC(O)NHC 6 H 7 (CH 3 ) 3 CH 2 HNCOOCH 2 CH 2 N 3 、
OCNC 6 H 7 (CH 3 ) 3 CH 2 NHCOOCH 2 C≡CH、
OCNC 6 H 7 (CH 3 ) 3 CH 2 NHCOOCH 2 CH 2 N 3 、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、実施形態1〜3のいずれか一項に記載の混合物。
[実施形態5]
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、実施形態1〜4のいずれか一項に記載の混合物。
[実施形態6]
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、実施形態1〜5のいずれか一項に記載の混合物。
[実施形態7]
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、実施形態1〜6のいずれか一項に記載の混合物。
[実施形態8]
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、実施形態6に記載の混合物。
[実施形態9]
前記硬化剤が小分子である、実施形態7又は8に記載の混合物。
[実施形態10]
前記硬化剤が第二ポリマーである、実施形態7〜9のいずれか一項に記載の混合物。
[実施形態11]
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、実施形態10に記載の混合物。
[実施形態12]
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、実施形態1〜11のいずれか一項に記載の混合物。
[実施形態13]
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、実施形態12に記載の混合物。
[実施形態14]
実施形態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。
[実施形態15]
−C(O)O CH 2 CHCH 3 NC(O)NHC 6 H 7 (CH 3 ) 3 CH 2 HNCOOCH 2 C≡CH、
−C(O)O CH 2 CHCH 3 NC(O)NHC 6 H 7 (CH 3 ) 3 CH 2 HNCOOCH 2 CH 2 N 3 、
−OC(O)NHC 6 H 7 (CH 3 ) 3 CH 2 NHC(O)OCH 2 C≡CH、
−OC(O)NHC 6 H 7 (CH 3 ) 3 CH 2 NHC(O)OCH 2 CH 2 N 3 、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。
[実施形態16]
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、実施形態14又は15に記載の硬化性ポリマー組成物。
[実施形態17]
実施形態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。
[実施形態18]
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−N 3 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。
[実施形態19]
前記組成物が、
CH 3 C 2 H 3 NC(O)NHC 6 H 7 (CH 3 ) 3 CH 2 HNCOOCH 2 C≡CH、
CH 3 C 2 H 3 NC(O)NHC 6 H 7 (CH 3 ) 3 CH 2 HNCOOCH 2 CH 2 N 3 、
OCNC 6 H 7 (CH 3 ) 3 CH 2 NHCOOCH 2 C≡CH、及びOCNC 6 H 7 (CH 3 ) 3 CH 2 NHCOOCH 2 CH 2 N 3 のうちの少なくとも1つから選択される、実施形態18に記載の組成物。
[実施形態20]
(a)実施形態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。
[実施形態21]
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、実施形態20に記載の方法。
[実施形態22]
前記反応温度が前記架橋温度未満である、実施形態21に記載の方法。
[実施形態23]
前記反応温度が約0℃〜100℃である、実施形態21又は22に記載の方法。
[実施形態24]
前記架橋温度が約50℃〜200℃である、実施形態21又は22に記載の方法。
Claims (2)
- 混合物であって、
(a)ポリマー主鎖に沿って配置された、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有する非自己架橋性ポリマー;並びに
(b)(i)前記非自己架橋性ポリマーの前記反応部位と反応することができる第一官能基と
(ii)アルキン又はアジドの硬化剤により架橋することができるアルキン又はアジドから選択される第二官能基と、を含む修飾化合物であって、CH 3 C 2 H 3 NC(O)NHC 6 H 7 (CH 3 ) 3 CH 2 HNCOOCH 2 C≡CH、
CH 3 C 2 H 3 NC(O)NHC 6 H 7 (CH 3 ) 3 CH 2 HNCOOCH 2 CH 2 N 3 、
OCNC 6 H 7 (CH 3 ) 3 CH 2 NHCOOCH 2 C≡CH、
OCNC 6 H 7 (CH 3 ) 3 CH 2 NHCOOCH 2 CH 2 N 3 、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、修飾化合物、
を含む、混合物。 - (a)請求項1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。
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-
2010
- 2010-11-10 WO PCT/US2010/056104 patent/WO2011059994A2/en active Application Filing
- 2010-11-10 US US12/943,116 patent/US8703877B2/en not_active Expired - Fee Related
- 2010-11-10 JP JP2012538920A patent/JP5837502B2/ja not_active Expired - Fee Related
- 2010-11-10 EP EP10830608.5A patent/EP2499201B1/en not_active Not-in-force
- 2010-11-10 KR KR1020127015070A patent/KR20120115262A/ko not_active Application Discontinuation
- 2010-11-10 CN CN201080048411.8A patent/CN102597120B/zh not_active Expired - Fee Related
-
2014
- 2014-03-05 US US14/197,731 patent/US20140187722A1/en not_active Abandoned
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2016
- 2016-08-30 US US15/251,704 patent/US20160369069A1/en not_active Abandoned
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US20140187722A1 (en) | 2014-07-03 |
WO2011059994A3 (en) | 2011-09-09 |
US20110112254A1 (en) | 2011-05-12 |
EP2499201B1 (en) | 2017-05-10 |
JP2013510928A (ja) | 2013-03-28 |
US20160369069A1 (en) | 2016-12-22 |
CN102597120A (zh) | 2012-07-18 |
EP2499201A4 (en) | 2014-08-13 |
US8703877B2 (en) | 2014-04-22 |
WO2011059994A2 (en) | 2011-05-19 |
EP2499201A2 (en) | 2012-09-19 |
CN102597120B (zh) | 2015-05-27 |
KR20120115262A (ko) | 2012-10-17 |
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