JP2009249568A - 室温硬化性フルオロポリエーテルゴム組成物及びその硬化物 - Google Patents
室温硬化性フルオロポリエーテルゴム組成物及びその硬化物 Download PDFInfo
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- JP2009249568A JP2009249568A JP2008101583A JP2008101583A JP2009249568A JP 2009249568 A JP2009249568 A JP 2009249568A JP 2008101583 A JP2008101583 A JP 2008101583A JP 2008101583 A JP2008101583 A JP 2008101583A JP 2009249568 A JP2009249568 A JP 2009249568A
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- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
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- 239000001993 wax Substances 0.000 description 1
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Classifications
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Abstract
【解決手段】
(A)1分子中に2個以上のアルケニル基を有するポリフルオロ化合物、
(B)1分子中に1個以上のパーフルオロオキシアルキル基、パーフルオロアルキル基、パーフルオロオキシアルキレン基、又はパーフルオロアルキレン基を有し、かつ1分子中にケイ素原子に結合した水素原子(Si−H基)を2個以上有する含フッ素オルガノハイドロジェンポリシロキサン、
(C)触媒量の白金族化合物、
(D)疎水性シリカ粉末、
(E)酸化防止剤
を必須成分としてなる室温硬化性フルオロポリエーテルゴム組成物。
【選択図】なし
Description
(A)1分子中に2個以上のアルケニル基を有するポリフルオロ化合物、
(B)1分子中に1個以上のパーフルオロオキシアルキル基、パーフルオロアルキル基、パーフルオロオキシアルキレン基、又はパーフルオロアルキレン基を有し、かつ1分子中にケイ素原子に結合した水素原子(Si−H基)を2個以上有する含フッ素オルガノハイドロジェンポリシロキサン、
(C)触媒量の白金族化合物、
(D)疎水性シリカ粉末、
(E)酸化防止剤
を必須成分としてなる室温硬化性フルオロポリエーテルゴム組成物が、室温下、短時間で硬化し、耐溶剤性、耐薬品性、耐熱性、低温特性、低透湿性、電気特性に優れ、かつ保存安定性にも優れる硬化物を与えることを見出し、本発明をなすに至った。
[1](A)下記一般式(1)で示されるポリフルオロ化合物
CH2=CH−(X)a−Rf−(X’)a−CH=CH2 (1)
[式中、Xは−CH2−,−CH2O−,−CH2OCH2−又は−Y−NR−CO−(Yは−CH2−又は下記構造式(Z)
−CtF2t−[OCF2CF(CF3)]p−O−CF2(CF2)rCF2−O−[CF(CF3)CF2O]q−CtF2t− (i)
(式中、p及びqは1〜150の整数であって、かつpとqの和は2〜200である。また、rは0〜6の整数、tは2又は3である。)
−CtF2t−[OCF2CF(CF3)]u−(OCF2)v−OCtF2t− (ii)
(式中、uは1〜200の整数、vは1〜50の整数である。また、tは上記と同じである。)]、
(B)1分子中に1個以上のパーフルオロオキシアルキル基、パーフルオロアルキル基、パーフルオロオキシアルキレン基、又はパーフルオロアルキレン基を有し、かつ1分子中にケイ素原子に結合した水素原子(Si−H基)を2個以上有する含フッ素オルガノハイドロジェンポリシロキサン、
(C)触媒量の白金族化合物、
(D)疎水性シリカ粉末、
(E)酸化防止剤
を必須成分としてなることを特徴とする室温硬化性フルオロポリエーテルゴム組成物。
[2][1]の組成物において、(A)成分、(C)成分、(D)成分及び(E)成分、並びに(A)成分、(B)成分及び(D)成分との2組成物とし、使用時に混合する使用形態をとることを特徴とする室温硬化性フルオロポリエーテルゴム組成物。
[3][1]又は[2]の組成物を加熱硬化することにより得られる硬化物。
〔(A)成分〕
(A)成分は、1分子中に2個以上のアルケニル基を有するポリフルオロ化合物であり、下記一般式(1)で表されるものが好ましい。
CH2=CH−(X)a−Rf−(X’)a−CH=CH2 (1)
[式中、Xは−CH2−,−CH2O−,−CH2OCH2−又は−Y−NR−CO−(Yは−CH2−又は下記構造式(Z)
−CtF2t−[OCF2CF(CF3)]p−O−CF2(CF2)rCF2−O−[CF(CF3)CF2O]q−CtF2t− (i)
(式中、p及びqは1〜150の整数であって、かつpとqの和は2〜200である。また、rは0〜6の整数、tは2又は3である。)
−CtF2t−[OCF2CF(CF3)]u−(OCF2)v−OCtF2t− (ii)
(式中、uは1〜200の整数、vは1〜50の整数である。tは上記と同じである。)
(B)成分は、1分子中にケイ素原子に直結した水素原子(Si−H基)を2個以上、好ましくは3個以上有する含フッ素オルガノハイドロジェンポリシロキサンであり、上記(A)成分の架橋剤ないし鎖長延長剤として機能するものである。
CgF2g+1−
(式中、gは1〜20、好ましくは2〜10の整数である。)
−CgF2g−
(式中、gは1〜20、好ましくは2〜10の整数である。)
F−[CF(CF3)CF2O]f−ChF2h−
(式中、fは2〜200、好ましくは2〜100の整数、hは1〜3の整数である。)
−CF(CF3)−[OCF2CF(CF3)]i−O−CF2CF2−O−[CF(CF3)CF2O]j−CF(CF3)−
(式中、i及びjは1以上の整数、i+jは2〜200、好ましくは2〜100である。)
−(CF2CF2O)r−(CF2O)s−CF2−
(式中、r及びsは1以上の整数であり、r+sは2〜200、好ましくは2〜100である。)
−CH2CH2−,
−CH2CH2CH2−,
−CH2CH2CH2OCH2−,
−CH2CH2CH2−NH−CO−,
−CH2CH2CH2−N(Ph)−CO−(但し、Phはフェニル基である。),
−CH2CH2CH2−N(CH3)−CO−,
−CH2CH2CH2−O−CO−,及び
−Ph’−N(CH3)−CO−(但し、Ph’はフェニレン基である。)
等の炭素数2〜12のものが挙げられる。
(C)成分は、ヒドロシリル化反応触媒であり、(A)成分中のアルケニル基と(B)成分中のヒドロシリル基との付加反応を促進する触媒である。このヒドロシリル化反応触媒は、一般に貴金属の化合物であり、高価格であることから、比較的入手し易い白金又は白金化合物がよく用いられる。
(D)成分は、疎水性シリカ粉末であり、上記組成物から得られる硬化物に適切な物理的強度を付与するものである。
(E)成分は、酸化防止剤であり、(A)成分のアルケニル基を含む有機基の酸化を抑制し、(C)成分である白金族化合物の触媒活性が低下するのを防止するためのものである。本発明のように室温下、短時間で硬化することを特徴とする組成物の場合は、(C)成分である白金族化合物の添加量を多くしているため、(A)成分のアルケニル基を含む有機基が酸化劣化を受け易い。特にアルケニル基が酸化された場合は、硬化反応に供する官能基量が減少してしまうばかりでなく、酸化によって生成したハイドロパーオキサイド等が、白金族化合物の触媒活性を低下させてしまう。長期間の保存中に、このようなことが原因で硬化不良や硬化遅延が起こってしまうのを防止するために、(E)成分である酸化防止剤の添加が必須となる。
で示される1価フェノール類及び2価フェノール類、例えば、フェノール、o−クレゾール、m−クレゾール、p−クレゾール、カテコール、レゾルシノール、ヒドロキノン、2,6−ジ−t−ブチル−4−メチルフェノール、2,6−ジ−t−ブチル−4−エチルフェノール、2,4−ジメチル−6−(1−メチルシクロヘキシル)フェノール、2,5−ジ−t−ブチル−ヒドロキノン、2,5−ジ−t−ペンチル−ヒドロキノン等や、下記式で示される多核フェノール類等が挙げられる。
本発明に係る室温硬化性フルオロポリエーテルゴム組成物においては、その実用性を高めるために上記(A)〜(E)成分以外にも、可塑剤、粘度調節剤、可撓性付与剤、ヒドロシリル化反応触媒の制御剤、無機質充填剤(但し、上記(D)成分は除く。)等の各種配合剤を必要に応じて添加することができる。これら添加剤の配合量は、本発明の目的を損なわない範囲、及び組成物の特性及び硬化物の物性を損なわない限りにおいて任意である。
Rf2−(X’)a−CH=CH2 (2)
[式中、X’及びaは上記と同じであり、Rf2は、下記一般式(iii):
F−[CF(CF3)CF2O]w−CtF2t− (iii)
(式中、tは上記と同じである。wは1〜150の整数であり、かつ、上記(A)成分の
Rf基に関するp+q及びrの和、並びにu及びvの和のいずれの和よりも小さい。)で表される基である。]
A−O−(CF2CF2CF2O)c−A (3)
(式中、Aは式:CsF2s+1−(sは1〜3)で表される基であり、cは1〜200の整数であり、かつ、前記(A)成分のRf基に関するp+q及びrの和、並びにu及びvの和のいずれの和よりも小さい。)
A−O−(CF2O)d(CF2CF2O)e−A (4)
(式中、Aは上記と同じであり、d及びeはそれぞれ1〜200の整数であり、かつ、dとeの和は、前記(A)成分のRf基に関するp+q及びrの和、並びにu及びvの和のいずれの和よりも小さい。)
CF3O−(CF2CF2CF2O)n−CF2CF3
CF3−[(OCF2CF2)n(OCF2)m]−O−CF3
(式中、m、nは整数であり、m+n=1〜200,m=1〜200,n=1〜200である。)
本発明の組成物の製造方法は特に限定されず、例えば、上記(A)〜(E)成分、及びその他の任意成分をロスミキサー、プラネタリーミキサー、ホバートミキサー、二本ロール等の混合装置により均一に混合する方法が挙げられる。
[実施例1〜3、比較例1]
D−1:Aerosil R976(Aerosil社製)
1.硬化性の評価
実施例1〜3及び比較例1における組成Aと組成Bの組成物をよく混練し、100×150×2mmの型枠に流し込んで、室温(23℃)で1時間放置し、その硬化状態を観測した。結果を表2に示した。
2.保存安定性の評価
実施例1〜3及び比較例1における組成Aと組成Bの組成物を40℃で2週間放置した後、1.と同様の方法で硬化性の評価を行い、初期の硬化性との比較を行った。結果を表2に示した。
3.ゴム物性の評価
1.硬化性の評価で作製した硬化物のゴム物性を測定した。結果を表2に示した。
Claims (3)
- (A)下記一般式(1)で示されるポリフルオロ化合物
CH2=CH−(X)a−Rf−(X’)a−CH=CH2 (1)
[式中、Xは−CH2−,−CH2O−,−CH2OCH2−又は−Y−NR−CO−(Yは−CH2−又は下記構造式(Z)
−CtF2t−[OCF2CF(CF3)]p−O−CF2(CF2)rCF2−O−[CF(CF3)CF2O]q−CtF2t− (i)
(式中、p及びqは1〜150の整数であって、かつpとqの和は2〜200である。また、rは0〜6の整数、tは2又は3である。)
−CtF2t−[OCF2CF(CF3)]u−(OCF2)v−OCtF2t− (ii)
(式中、uは1〜200の整数、vは1〜50の整数である。また、tは上記と同じである。)]、
(B)1分子中に1個以上のパーフルオロオキシアルキル基、パーフルオロアルキル基、パーフルオロオキシアルキレン基、又はパーフルオロアルキレン基を有し、かつ1分子中にケイ素原子に結合した水素原子(Si−H基)を2個以上有する含フッ素オルガノハイドロジェンポリシロキサン、
(C)触媒量の白金族化合物、
(D)疎水性シリカ粉末、
(E)酸化防止剤
を必須成分としてなることを特徴とする室温硬化性フルオロポリエーテルゴム組成物。 - 請求項1記載の組成物において、(A)成分、(C)成分、(D)成分及び(E)成分、並びに(A)成分、(B)成分及び(D)成分との2組成物とし、使用時に混合する使用形態をとることを特徴とする室温硬化性フルオロポリエーテルゴム組成物。
- 請求項1又は2記載の組成物を加熱硬化することにより得られる硬化物。
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Cited By (6)
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WO2011052757A1 (ja) | 2009-10-29 | 2011-05-05 | 日本ポリプロ株式会社 | プロピレン系重合体の製造方法 |
JP2011219692A (ja) * | 2010-04-14 | 2011-11-04 | Shin-Etsu Chemical Co Ltd | 接着剤組成物 |
JP2016145354A (ja) * | 2015-02-04 | 2016-08-12 | 信越化学工業株式会社 | 光硬化性フルオロポリエーテル系ゴム組成物及びその硬化物、並びにその硬化方法 |
LT6538B (lt) | 2016-11-18 | 2018-06-25 | Uab "Airplus1 Lituanica" | Eskalatoriaus turėklo juostos dezinfekavimo sistema ir būdas |
JP2019038904A (ja) * | 2017-08-23 | 2019-03-14 | 信越化学工業株式会社 | 硬化性パーフルオロポリエーテル粘着剤組成物、その硬化物を用いた粘着剤並びに粘着テープ |
WO2021251151A1 (ja) * | 2020-06-11 | 2021-12-16 | 信越化学工業株式会社 | パーフルオロポリエーテルブロックを有するオルガノハイドロジェンポリシロキサン、及びその製造方法 |
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JP2009091547A (ja) * | 2007-09-21 | 2009-04-30 | Shin Etsu Chem Co Ltd | 付加硬化型シリコーンゴム組成物及びその硬化物並びに架橋剤 |
JP5799930B2 (ja) * | 2012-10-19 | 2015-10-28 | 信越化学工業株式会社 | 硬化性フルオロポリエーテル系ゲル組成物及びその硬化物を用いたゲル製品 |
JP6160540B2 (ja) * | 2014-03-31 | 2017-07-12 | 信越化学工業株式会社 | 硬化性パーフルオロポリエーテル系ゲル組成物及びその硬化物を用いたゲル製品 |
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JP2002167502A (ja) * | 2000-11-30 | 2002-06-11 | Shin Etsu Chem Co Ltd | 硬化性フルオロポリエーテル系ゴム組成物 |
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JP2001192546A (ja) * | 2000-01-07 | 2001-07-17 | Shin Etsu Chem Co Ltd | 硬化性フルオロポリエーテル系ゴム組成物 |
JP4016239B2 (ja) * | 2000-07-05 | 2007-12-05 | 信越化学工業株式会社 | 硬化性フルオロポリエーテル系ゴム組成物 |
JP3748054B2 (ja) | 2001-06-28 | 2006-02-22 | 信越化学工業株式会社 | 室温硬化性オルガノポリシロキサン組成物 |
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EP1818367B1 (en) * | 2006-02-13 | 2009-07-15 | Shin-Etsu Chemical Co., Ltd. | Curable fluoropolyether compositions and integral molded resin/rubber articles |
JP5303864B2 (ja) * | 2007-05-21 | 2013-10-02 | 信越化学工業株式会社 | 硬化性フルオロポリエーテル組成物及びそれを用いたゴム硬化物と有機樹脂との一体成型品 |
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- 2008-04-09 JP JP2008101583A patent/JP5035555B2/ja not_active Expired - Fee Related
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2009
- 2009-04-03 US US12/418,046 patent/US20090258986A1/en not_active Abandoned
- 2009-04-09 EP EP09251071A patent/EP2108672A1/en not_active Withdrawn
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JP2002167502A (ja) * | 2000-11-30 | 2002-06-11 | Shin Etsu Chem Co Ltd | 硬化性フルオロポリエーテル系ゴム組成物 |
WO2004050758A1 (ja) * | 2002-12-05 | 2004-06-17 | Daikin Industries, Ltd. | 含フッ素ポリマー組成物及び硬化体 |
WO2005116134A1 (ja) * | 2004-05-28 | 2005-12-08 | Kaneka Corporation | 硬化性組成物およびその硬化物 |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2011052757A1 (ja) | 2009-10-29 | 2011-05-05 | 日本ポリプロ株式会社 | プロピレン系重合体の製造方法 |
JP2011219692A (ja) * | 2010-04-14 | 2011-11-04 | Shin-Etsu Chemical Co Ltd | 接着剤組成物 |
JP2016145354A (ja) * | 2015-02-04 | 2016-08-12 | 信越化学工業株式会社 | 光硬化性フルオロポリエーテル系ゴム組成物及びその硬化物、並びにその硬化方法 |
LT6538B (lt) | 2016-11-18 | 2018-06-25 | Uab "Airplus1 Lituanica" | Eskalatoriaus turėklo juostos dezinfekavimo sistema ir būdas |
JP2019038904A (ja) * | 2017-08-23 | 2019-03-14 | 信越化学工業株式会社 | 硬化性パーフルオロポリエーテル粘着剤組成物、その硬化物を用いた粘着剤並びに粘着テープ |
WO2021251151A1 (ja) * | 2020-06-11 | 2021-12-16 | 信越化学工業株式会社 | パーフルオロポリエーテルブロックを有するオルガノハイドロジェンポリシロキサン、及びその製造方法 |
JP2021195426A (ja) * | 2020-06-11 | 2021-12-27 | 信越化学工業株式会社 | パーフルオロポリエーテルブロックを有するオルガノハイドロジェンポリシロキサン、及びその製造方法 |
JP7306334B2 (ja) | 2020-06-11 | 2023-07-11 | 信越化学工業株式会社 | パーフルオロポリエーテルブロックを有するオルガノハイドロジェンポリシロキサン、及びその製造方法 |
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EP2108672A1 (en) | 2009-10-14 |
JP5035555B2 (ja) | 2012-09-26 |
US20090258986A1 (en) | 2009-10-15 |
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