JP2013028819A - 硬化性組成物および触媒組成物 - Google Patents
硬化性組成物および触媒組成物 Download PDFInfo
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- JP2013028819A JP2013028819A JP2012237025A JP2012237025A JP2013028819A JP 2013028819 A JP2013028819 A JP 2013028819A JP 2012237025 A JP2012237025 A JP 2012237025A JP 2012237025 A JP2012237025 A JP 2012237025A JP 2013028819 A JP2013028819 A JP 2013028819A
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- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
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Abstract
【解決手段】シロキサン結合を形成することにより架橋し得るケイ素含有基を有する重合体(A)と、フッ化塩化合物(B1)と、アミン化合物(F)とを含む硬化性組成物。フッ化塩化合物(B1)は、フッ化置換アンモニウム塩あるいはフッ化非置換アンモニウム塩であって、該フッ化置換アンモニウム塩で置換基が炭化水素基の場合あるいは該フッ化非置換アンモニウム塩の場合には、前記フッ化塩化合物(B)は一般式(1):
R4−mNHmF・(HF)n
(式中Rは置換あるいは非置換の炭化水素基、0≦m≦4、nは0または正の数を表し、mおよびnが同時に0となることはない)で表されるフッ化塩化合物。
【選択図】 なし
Description
一方、(特許文献5)中には、フッ素アニオンを有する化合物として4級アンモニウムフルオライド塩、アルカリ金属のフッ化塩等が例示されている。
(1)シロキサン結合を形成することにより架橋し得るケイ素含有基を有する重合体(A)と、フッ化塩化合物(B)と、アミン化合物(F)とを含む硬化性組成物であって、
前記フッ化塩化合物(B)が、以下のフッ化塩化合物(B1)である硬化性組成物。
フッ化塩化合物(B1):フッ化置換アンモニウム塩あるいはフッ化非置換アンモニウム塩であって、該フッ化置換アンモニウム塩で置換基が炭化水素基の場合あるいは該フッ化非置換アンモニウム塩の場合には、前記フッ化塩化合物(B)は一般式(1):
R4−mNHmF・(HF)n
(式中Rは置換あるいは非置換の炭化水素基、0≦m≦4、nは0または正の数を表し、mおよびnが同時に0となることはない)で表されるフッ化塩化合物。
(2)前記フッ化塩化合物(B1)がアンモニウムハイドロフルオライド化合物(B2)である(1)に記載の硬化性組成物。
(3)前記フッ化塩化合物(B1)が1級、2級、あるいは3級のフッ化置換アンモニウム塩化合物(B3)である(1)または(2)に記載の硬化性組成物。
(4)前記フッ化塩化合物(B)の最大粒子径が150μm以下である(1)〜(3)のいずれかに記載の硬化性組成物。
(5)前記フッ化塩化合物(B)が一般式(2):
(6)前記アミン化合物(F)がアミジン化合物である(1)〜(5)のいずれかに記載の硬化性組成物。
(7)前記アミン化合物(F)がアミノ基を有する3級アミン化合物である(1)〜(5)のいずれかに記載の硬化性組成物。
(8)前記フッ化塩化合物(B)の合計モル数に対する、前記アミン化合物(F)の合計モル数の比が0.1〜10である(1)〜(7)のいずれかに記載の硬化性組成物。
(9)酸化合物(G)をさらに含む(1)〜(8)のいずれかに記載の硬化性組成物。
(10)前記酸化合物(G)がカルボン酸である(9)に記載の硬化性組成物。
(11)前記アミン化合物(F)の合計モル数に対する前記酸化合物(G)の合計モル数の比が0.5〜2である(10)に記載の硬化性組成物。
(12)前記酸化合物(G)が、カルボン酸無水物である(9)に記載の硬化性組成物。
(13)前記アミン化合物(F)のモル数に対する前記酸化合物(G)中のカルボン酸無水物基のモル数が0.1〜1である(12)に記載の硬化性組成物。
(14)充填剤(C)をさらに含む(1)〜(13)のいずれかに記載の硬化性組成物であって、前記充填剤(C)が、脂肪酸以外で表面処理された沈降炭酸カルシウム、脂肪酸で表面処理された沈降炭酸カルシウム(前記フッ化塩化合物(B)中に含有されるフッ素原子と、前記脂肪酸で表面処理された沈降炭酸カルシウムとの重量比が0.0015以上を満たす。)、重質炭酸カルシウムおよびシリカからなる群より選択される少なくとも1種以上である硬化性組成物。
(15)プロトン酸(D)をさらに含む(1)〜(14)のいずれかに記載の硬化性組成物。
(16)前記プロトン酸(D)は、脂肪酸である(15)に記載の硬化性組成物。
(17)前記プロトン酸(D)は、スルホン酸である(15)に記載の硬化性組成物。
(18)前記プロトン酸(D)が供与し得るH+イオンのモル数と、前記フッ化塩化合物(B)中のフッ素原子のモル数との比が0.1以上である(15)〜(17)のいずれかに記載の硬化性組成物。
(19)スルホン酸以外のスルホニル基を有する化合物(E)を更に含む(1)〜(18)のいずれに記載の硬化性組成物。
(20)前記スルホニル基を有する化合物(E)のモル数と、フッ化塩化合物(B)のフッ素原子のモル数との比が0.5以上である(19)に記載の硬化性組成物。
(21)前記重合体(A)100重量部に対して、0.001〜30重量部の前記フッ化塩化合物(B)を含有する(1)〜(20)のいずれかに記載の硬化性組成物。
(22)前記重合体(A)100重量部に対して、5〜500重量部の前記充填剤(C)を含有する(14)〜(21)のいずれかに記載の硬化性組成物。
(23)前記重合体(A)は、シロキサン結合を形成することにより架橋し得るケイ素含有基を1分子あたり平均して1個以上有する重合体である(1)〜(22)のいずれかに記載の硬化性組成物。
(24)前記重合体(A)が有するシロキサン結合を形成することにより架橋し得るケイ素含有基が、下記一般式(3):
−SiR1 3−aXa (3)
(式中、(3−a)個のR1は、それぞれ独立に、炭素原子数1から20の炭化水素基あるいはR2 3SiO−(3個のR2はそれぞれ独立に、炭素原子数1から20の炭化水素基である。)で示されるシロキシ基であり、a個のXはそれぞれ独立に、水酸基、アルコキシ基、アルケニルオキシ基、アシルオキシ基、フェノキシ基からなる群より選択される基である。また、aは1,2,3のいずれかである。)で表される(1)〜(23)のいずれかに記載の硬化性組成物。
(25)一般式(3)中に記載のaが2である(24)に記載の硬化性組成物。
(26)一般式(3)中に記載のXがアルコキシ基である(24)または(25)に記載の硬化性組成物。
(27)前記重合体(A)の数平均分子量が3,000〜100,000である(1)〜(26)のいずれかに記載の硬化性組成物。
(28)前記重合体(A)は、ポリオキシアルキレン系重合体、飽和炭化水素系重合体、および(メタ)アクリル酸エステル系重合体からなる群から選択される少なくとも1種の主鎖骨格を有する重合体である、(1)〜(27)のいずれかに記載の硬化性組成物。
(29)1〜28のいずれかに記載の硬化性組成物を用いてなるシーリング材。
(30)1〜28のいずれかに記載の硬化性組成物を用いてなる接着剤。
(31)フッ化塩化合物(B)と、アミン化合物(F)と、を含む、シロキサン結合を形成することにより架橋し得るケイ素含有基を有する重合体(A)の硬化のために用いられる触媒組成物。
(32)前記酸化合物(G)をさらに含む(31)に記載の触媒組成物。
(33)分散剤(H)をさらに含む(31)または(32)に記載の触媒組成物。
(34)シロキサン結合を形成することにより架橋し得るケイ素含有基を有する重合体(A)と、(31)〜(33)のいずれかに記載の触媒組成物と、を含む硬化性組成物。
<シロキサン結合を形成することにより架橋し得るケイ素含有基を有する重合体(A)>
本発明に用いる上記重合体の主鎖骨格は特に制限はなく、各種の主鎖骨格を持つもの、好ましくは有機重合体を使用することができる。
−SiR1 3−aXa (3)
(式中、(3−a)個のR1は、それぞれ独立に、炭素原子数1から20の炭化水素基あるいはR2 3SiO−(3個のR2はそれぞれ独立に、炭素原子数1から20の炭化水素基である。)で示されるシロキシ基であり、a個のXはそれぞれ独立に、水酸基、アルコキシ基、アルケニルオキシ基、アシルオキシ基、フェノキシ基からなる群より選択される基である。また、aは1,2,3のいずれかである。)で表される基を挙げることができる。
H−SiX3 (4)
(式中、Xは、上記一般式(3)と同じ。)で表されるヒドロシラン化合物は、該ヒドロシラン化合物の付加反応により得られる有機重合体からなる硬化性組成物の硬化性が優れることから好ましい。一般式(4)で表されるヒドロシラン化合物の中で、トリメトキシシラン、トリエトキシシラン、および、トリイソプロポキシシラン等のトリアルコキシシラン類がより好ましい。
H−Si(OR5)3 (5)
(式中、3個のR5は、それぞれ独立に炭素原子数2から20の有機基である)で表される炭素原子数が2以上のアルコキシ基を有するトリアルコキシシランを用いることが好ましい。入手性、取り扱い上の安全性の観点から、トリエトキシシランが最も好ましい。
−R6−O− (6)
(式中、R6は炭素原子数1から14の直鎖状もしくは分岐アルキレン基である。)で示される繰り返し単位を有する重合体である。好ましくは、一般式(6)におけるR6は、炭素原子数2から4の直鎖状もしくは分岐状アルキレン基である。一般式(6)で示される繰り返し単位の具体例としては、
−CH2−C(R7)(COOR8)− (7)
(式中、R7は水素原子またはメチル基、R8は炭素原子数1から8のアルキル基を示す)で表される炭素原子数1から8のアルキル基を有する(メタ)アクリル酸エステル単量体単位と、下記一般式(8):
−CH2−C(R7)(COOR9)− (8)
(式中、R7は前記に同じ、R9は炭素原子数10以上のアルキル基を示す)で表される炭素原子数10以上のアルキル基を有する(メタ)アクリル酸エステル単量体単位からなる共重合体に、反応性ケイ素基を有するポリオキシアルキレン系重合体をブレンドして製造する方法である。
−NR10−C(=O)− (9)
(R10は、水素原子または置換あるいは非置換の有機基を表す)で表される基である。
W−R11−SiR1 3−aXa (10)
(ただし、式中、R1、X、aは上記一般式(3)に同じ。R11は、2価の有機基であり、より好ましくは炭素原子数1から20の置換もしくは非置換の2価の炭化水素基である。Wは水酸基、カルボキシル基、メルカプト基、非置換または一置換のアミノ基から選ばれた活性水素含有基である。)で表されるケイ素化合物のW基を反応させる方法により製造されるものを挙げることができる。この製造方法に関連した、有機重合体の公知の製造法を例示すると、特公昭46−12154号(米国特許3632557号)、特開昭58−109529号(米国特許4374237号)、特開昭62−13430号(米国特許4645816号)、特開平8−53528号(EP0676403)、特開平10−204144号(EP0831108)、特表2003−508561(米国特許6197912号)、特開平6−211879号(米国特許5364955号)、特開平10−53637号(米国特許5756751号)、特開平11−100427号、特開2000−169544号、特開2000−169545号、特開2002−212415号、特許第3313360号、米国特許4067844号、米国特許3711445号、特開2001−323040号、などが挙げられる。
O=C=N−R11−SiR1 3−aXa (11)
(ただし、式中R1、R11、X、aは一般式(3)、(10)に同じ。)で示される反応性ケイ素基含有イソシアネート化合物とを反応させることにより製造されるものを挙げることができる。この製造方法に関連した、有機重合体の公知の製造法を例示すると、特開平11−279249号(米国特許5990257号)、特開2000−119365号(米国特許6046270号)、特開昭58−29818号(米国特許4345053号)、特開平3−47825号(米国特許5068304号)、特開平11−60724号、特開2002−155145号、特開2002−249538号、WO03/018658、WO03/059981などが挙げられる。
また、上記方法により、一般式(10)または一般式(11)の化合物を用いて製造される有機重合体の中で、R11が−CH2−である化合物からなる有機重合体は、特に優れた硬化性が得られる傾向にある。
<フッ化塩化合物(B)>
本発明の硬化性組成物は、上記反応性ケイ素基を有する有機重合体(A)の硬化触媒としてフッ化塩化合物(B)を含有する。ここで言うフッ化塩化合物とは、フッ素アニオンとして作用し得る化合物のことである。
R4−mNHmF・(HF)n
(式中Rは置換あるいは非置換の炭化水素基、0≦m≦4、nは0または正の数を表し、mおよびnが同時に0となることはない)で表されるフッ化塩化合物(B1)が好ましく用いられる。
(HF)nF− (13)
(式中、nは0または正の数を表わす。)で表される構造である。
<充填剤(C)>
本発明の硬化性組成物は、さらに脂肪酸以外で表面処理された沈降炭酸カルシウム、脂肪酸で表面処理された沈降炭酸カルシウム(前記フッ化塩化合物(B)中に含有されるフッ素原子と、前記脂肪酸で表面処理された沈降炭酸カルシウムとの重量比が0.0015以上を満たす。)、重質炭酸カルシウムおよびシリカからなる群から選択される少なくとも1種以上である充填剤(C)を含有することができる。
<その他の充填剤>
硬化性組成物として作業性(キレなど)が求められる場合や、得られる硬化物の表面が艶消し状であることが求められる場合、添加される充填剤は、有機バルーン、無機バルーンが添加できる。これらの充填剤は表面処理の有無を問わず、また、1種類のみを添加してもよいし、複数種を組み合わせて添加してもよい。バルーンの粒子径は、作業性(キレなど)を向上させる目的では、0.1mm以下が好ましく、硬化物の表面を艶消し状にする目的では、5〜300μmが好ましい。
<プロトン酸(D)>
本発明では、プロトン酸(D)を用いることで、硬化性組成物を取り扱う際の作業性を改善する効果が得られる。
<スルホニル基を有する化合物(E)>
次に、さらに硬化性を向上させるために硬化触媒と共に用いられるスルホニル基を有する化合物(E)について説明する。スルホニル基を有する化合物(E)は分子中に−S(=O)2−で示される官能基を有する化合物のことを言う。
<アミン化合物(F)>
フッ化塩化合物(B)が、フッ化非置換アンモニウム塩及び/又はフッ化水素非置換アンモニウム塩である場合、あるいはアンモニウムハイドロフルオライド化合物である場合にはさらにアミン化合物(F)を含むことが好ましい。
R12N=CR13−NR14 2 (14)
(R12、R13、および2個のR14は、それぞれ独立に、水素原子または有機基である。)で示される化合物であり、さらに具体的にはたとえば、グアニジン、1,1,3,3−テトラメチルグアニジン、1−ブチルグアニジン、1−フェニルグアニジン、1−o−トリルグアニジン、1,3−ジフェニルグアニジンなどのグアニジン類化合物;ブチルビグアニド、1−o−トリルビグアニドや1−フェニルビグアニドなどのビグアニド類化合物;イミダゾール、2−エチル−4−メチルイミダゾールなどのイミダゾール類化合物;2−メチルイミダゾリン、2−ウンデシルイミダゾリン、2−フェニルイミダゾリン、4,4−ジメチル−2−イミダゾリンなどのイミダゾリン類化合物の他、1,8−ジアザビシクロ[5,4,0]−7−ウンデセン(DBU)、6−(ジブチルアミノ)−1,8−ジアザビシクロ[5,4,0]−7−ウンデセン(DBA−DBU)、1,5−ジアザビシクロ[4,3,0]−5−ノネン(DBN)、1,3,4,6,7,8−ヘキサヒロドロ−2H−ピリミドピリジン、1,4,5,6−テトラヒドロピジミジン、1,2−ジメチルテトラヒドロピリミジンなどが例示される。
本発明の硬化性組成物にはフッ化塩化合物(B)とともに酸化合物(G)を用いてもよい。
<分散剤(H)>
本発明の触媒組成物には、分散剤(H)を使用することができる。分散剤(H)は触媒組成物を重合体(A)に分散しやすくし、優れた硬化性を得るために用いられ、より優れた硬化性を得るためには、分散剤(H)を使用することが好ましい。
<その他の成分>
本発明の硬化性組成物中には、必要に応じて、接着性付与剤を添加することができる。接着付与剤としてはシランカップリング剤が例示される。
<硬化性組成物の調整法>
本発明の硬化性組成物の調製法としては、特に限定はなく、たとえば、前記した配合成分を調合し、ミキサーやロールやニーダーなどを用いて常温または加熱下で混練する方法、適した溶剤を少量使用して配合成分を溶解させたのち混合する方法など公知の方法が採用されうる。
<触媒組成物の調整法>
本発明の触媒組成物は、フッ化塩化合物(B)、アミン化合物(F)、好ましくは酸化合物(G)あるいは/および分散剤(H)を必須成分とするが、これら必須成分は必ずしも触媒組成物中に単体として存在する必要は無く、必須成分等の混合によって発生する反応物として存在してもよい。また、本発明では前記必須成分とは、必須成分由来の化合物を含むことを意味するものである。
<用途例>
本発明の硬化性組成物は、大気中に暴露されると水分の作用により、三次元的に網状組織を形成し、ゴム状弾性を有する固体へと硬化する。
分子量約3,000のポリオキシプロピレントリオールを開始剤とし、亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキシドの重合を行ない、末端が水酸基である数平均分子量約26,000(送液システムとして東ソー製HLC−8120GPCを用い、カラムは東ソー製TSK−GEL Hタイプを用い、溶媒はTHFを用いて測定したポリスチレン換算分子量)のポリプロピレンオキシドを得た。続いて、この水酸基末端ポリプロピレンオキシドの水酸基に対して1.2倍当量のNaOMeのメタノール溶液を添加してメタノールを留去し、さらに塩化アリルを添加して末端の水酸基をアリル基に変換した。未反応の塩化アリルを減圧脱揮により除去した。得られた未精製のアリル基末端ポリプロピレンオキシド100質量部に対し、n−ヘキサン300質量部と、水300質量部を混合攪拌した後、遠心分離により水を除去し、得られたヘキサン溶液にさらに水300質量部を混合攪拌し、再度遠心分離により水を除去した後、ヘキサンを減圧脱揮により除去した。以上により、末端がアリル基である数平均分子量約26,000の3官能ポリプロピレンオキシド(P−1)を得た。
分子量約2,000のポリオキシプロピレンジオールと分子量約3,000のポリオキシプロピレントリオールの1/1(質量比)混合物を開始剤とし、亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキシドの重合を行ない、数平均分子量約19,000のポリプロピレンオキシドを得た。続いて、この水酸基末端ポリプロピレンオキシドの水酸基に対して1.2倍当量のNaOMeのメタノール溶液を添加してメタノールを留去し、更に塩化アリルを添加して末端の水酸基をアリル基に変換した。以上により、末端がアリル基である数平均分子量約19,000のポリプロピレンオキシドを得た。得られた未精製のアリル基末端ポリプロピレンオキシド100質量部に対し、n−ヘキサン300質量部と、水300質量部を混合攪拌した後、遠心分離により水を除去し、得られたヘキサン溶液に更に水300質量部を混合攪拌し、再度遠心分離により水を除去した後、ヘキサンを減圧脱揮により除去し、精製されたアリル基末端ポリプロピレンオキシド(P−2)を得た。
分子量約2,000のポリオキシプロピレンジオールを開始剤とし、亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキシドの重合を行い、末端が水酸基である数平均分子量約25,500(送液システムとして東ソー製HLC−8120GPCを用い、カラムは東ソー製TSK−GEL Hタイプを用い、溶媒はTHFを用いて測定したポリスチレン換算分子量)のポリプロピレンオキシドを得た。続いて、この水酸基末端ポリプロピレンオキシドの水酸基に対して1.2倍当量のNaOMeのメタノール溶液を添加してメタノールを留去し、さらに塩化アリルを添加して末端の水酸基をアリル基に変換した。未反応の塩化アリルを減圧脱揮により除去した。得られた未精製のアリル基末端ポリプロピレンオキシド100質量部に対し、n−ヘキサン300質量部と、水300質量部を混合攪拌した後、遠心分離により水を除去し、得られたヘキサン溶液に、さらに水300質量部を混合攪拌し、再度遠心分離により水を除去した後、ヘキサンを減圧脱揮により除去した。以上により、末端がアリル基である数平均分子量約25,500の2官能ポリプロピレンオキシド(P−3)を得た。
表2に示す処方に従い、有機重合体(A−1)と充填剤をスパチュラで混合し、3本ロールを用いて均一に分散させ、主剤とした。各主剤に対し、硬化触媒としてテトラブチルフッ化アンモニウムのTHF溶液を添加し、スパチュラを用いて素早く混合した。混合物を軟膏缶の蓋に流し込み、表面を平面状に整えた。この時間を硬化開始時間とし、はじめの1時間は5分毎に、以後1時間毎に表面をスパチュラで触り、スパチュラに配合物が付着しなくなった時間を皮張り時間として測定を行なった。さらに、1日後に硬化物を軟膏缶から取り外し、手で引張り、強度を判定した。十分に強度を有し、硬化物の破断に力を要したものをA、容易に破断したものをBとした。結果を表2に示す。
表3に示す処方に従い、有機重合体(A−2)と充填剤をスパチュラで混合し、3本ロールを用いて均一に分散させ、主剤とした。各主剤に対し、硬化触媒としてテトラブチルフッ化アンモニウムのTHF溶液を添加し、スパチュラを用いて素早く混合した。混合物を軟膏缶の蓋に流し込み、表面を平面状に整えた。この時間を硬化開始時間とし、はじめの1時間は5分毎に、以後1時間毎に表面をスパチュラで触り、スパチュラに配合物が付着しなくなった時間を皮張り時間として測定を行なった。また、厚さ3mmのシート状型枠に各混合物を充填し、表面を整えて、23℃×3日+50℃×4日の養生後、ダンベル型枠で打ち抜き、ダンベル型硬化物を作成した。このダンベル片を用いて、引張速度200mm/分で引張試験を行ない、破断時強度(MPa)および破断時伸び(%)を測定した。結果を表3に示す。表中、破断時強度が0.5MPa以上をA、0.5MPa未満をBと表記した。また、破断時伸びが200%以上をA、200%未満をBと表記した。
表4に示す処方に従って、上記と同じ要領で硬化性を評価した。結果を表4に示す。
表5に示す処方に従って、有機重合体(A−2)、充填剤および各種添加剤を混合し、3本ロールを用いて均一に分散させ、主剤とした。上記と同じ要領で硬化性を評価した。
結果を表5に示す。
表6に示す処方に従って、有機重合体(A−2)、充填剤および各種添加剤を混合し、3本ロールを用いて均一に分散させ、主剤とした。フッ化塩化合物(B)としてフッ化カリウムを用い、上記と同じ要領で硬化性を評価した。結果を表6に示す。フッ化カリウムは6.3質量%メタノール溶液として使用し、表中にはフッ化カリウム溶液量を示した。
表7に示す処方に従い、有機重合体(A−3)と充填剤、チクソ性付与剤をスパチュラで混合し、3本ロールを用いて均一に分散させ、主剤とした。各主剤に対し、硬化触媒としてフッ化塩化合物を添加し、スパチュラを用いて1分間よく混合した。混合物をヘラで薄く伸ばしながら脱泡したものを、軟膏缶の蓋に充填し、表面を平面状に整えた。この時間を硬化開始時間とし、はじめの1時間は5分毎に、以後1時間毎に表面をスパチュラで触り、スパチュラに配合物が付着しなくなった時間を皮張り時間として測定を行った。結果を表7に示す。
表8に示す処方に従って、有機重合体(A−2)、充填剤、各種添加剤を混合し、3本ロールを用いて均一に分散させ、主剤とした。上記と同じ要領で硬化性を評価した。結果を表8に示す。
(実施例19〜22、比較例12〜14)
23℃、50%RHの条件下、表9に示す処方に従って金属缶中に各成分を量りとり、スパチュラを用いて1分間よく混錬した。混練終了時間を硬化開始時間とし、金属缶を23℃、50%RHの条件下に静置した。スパチュラで組成物の一部を練り粘性液状からゴム弾性体となり始めるまでの時間をゲル化時間として硬化性を評価した。結果を表9に示す。
反応性ケイ素基を有する重合体(A)として合成例2で得られた重合体(A−2)100重量部、充填剤として表面処理膠質炭酸カルシウム(白石工業(株)製、商品名:白艶華CCR)120重量部、および酸化チタン(石原産業(株)製、商品名:タイペークR−820)20重量部を使用し、さらに、可塑剤(武田薬品工業(株)製、商品名:アクトコールP23)55重量部、チクソ性付与剤(楠本化成(株)製、商品名:ディスパロン#6500)2重量部、酸化防止剤((株)ワイ・エス・ケー製、商品名:ユノックスKC)1重量部、紫外線吸収剤(チバ・スペシャルティ・ケミカルズ(株)製、商品名:チヌビン327)1重量部、光安定剤(三共(株)製、商品名:サノールLS770)1重量部を使用し、各々計量、混合して充分混練りした後、3本ペイントロールを用いて分散させた。接着付与剤としてγ−(2−アミノエチル)アミノプロピルトリメトキシシラン(東レ・ダウコーニング(株)製、商品名:A−1120)3重量部、反応性ケイ素基を有する化合物としてビニルトリメトキシシラン(東レ・ダウコーニング(株)製、商品名:A−171)2重量部を加えて混練して主剤とした。
表11に示す化合物を、表11に示す重量部ずつ混合して反応させ、1級、2級、あるいは3級のフッ化置換アンモニウム塩化合物(B3)を含む混合物(B3−1〜B3−6)を得た。
23℃、50%RHの条件下、表12に示す処方に従って金属缶中に各成分を量りとり、スパチュラを用いて1分間よく混錬した。混練終了時間を硬化開始時間とし、金属缶を23℃、50%RHの条件下に静置した。スパチュラで組成物の一部を練り粘性液状からゴム弾性体となり始めるまでの時間をゲル化時間として硬化性を評価した。結果を表12に示す。
23℃、50%RHの条件下、金属缶中に実施例23〜26に用いたものと同一の主剤305重量部および合成例4で得られた生成物(B3−1)2.7重量部を量りとり、スパチュラを用いて1分間よく混錬した。混練終了時間を硬化開始時間とし、金属缶を23℃、50%RHの条件下に静置した。スパチュラで組成物の一部を練り粘性液状からゴム弾性体となり始めるまでの時間をゲル化時間として硬化性を評価したところ、ゲル時間は1分であった。
フッ化アンモニウムあるいはフッ化水素アンモニウムを乳鉢で粉砕した後、目開き150μmのふるいを通した。次いでこれに、表13に示す処方に従って分散剤(H)、アミン化合物(F)を加えてスパチュラでよく混合し、得られたペースト状物をそのまま触媒組成物とした。以下、実施例34〜47の触媒組成物を、それぞれ触媒組成物34〜47と称する。
23℃、50%RHの条件下、表14(実施例48〜60)および表15(比較例15〜16)に示す処方に従って金属缶中に各成分を量りとり、スパチュラを用いて1分間よく混錬した。混練終了時間を硬化開始時間とし、金属缶を23℃、50%RHの条件下に静置した。スパチュラで、金属缶中の組成物の一部を練り、粘性液状からゴム弾性体となり始めるまでの時間をゲル化時間として硬化性を評価した。結果を表14および表15に示す。
反応性ケイ素基を有する重合体(A)として合成例2で得られた重合体(A−2)100質量部、充填剤(C)として表面処理膠質炭酸カルシウム(白石工業(株)製、商品名:白艶華CCR)120質量部、および酸化チタン(石原産業(株)製、商品名:タイペークR−820)20質量部を使用し、さらに、可塑剤(三井化学ポリウレタン(株)製、商品名:アクトコールP23)55質量部、チクソ性付与剤(楠本化成(株)製、商品名:ディスパロン#6500)2質量部、酸化防止剤((株)ワイ・エス・ケー製、商品名:ユノックスKC)1質量部、紫外線吸収剤(チバ・スペシャルティ・ケミカルズ(株)製、商品名:チヌビン327)1質量部、光安定剤(三共(株)製、商品名:サノールLS770)1質量部を使用し、各々計量、混合して充分混練りした後、3本ペイントロールを用いて分散させた。さらに、接着付与剤として、γ−(2−アミノエチル)アミノプロピルトリメトキシシラン(東レ・ダウコーニング(株)製、商品名:A−1120)3質量部および反応性ケイ素基を有する化合物として、ビニルトリメトキシシラン(東レ・ダウコーニング(株)製、商品名:A−171)2質量部を加えて混練することにより、主剤を調製した。
23℃、50%RHの条件下、金属缶中に、反応性ケイ素基を有する重合体(A)として合成例2で得られた重合体(A−2)100質量部、および実施例34〜47で用いた最大粒径150μm以下のフッ化水素アンモニウムを2倍重量のメタノールと混合して得られたペースト1.0質量部を量りとり、スパチュラを用いて1分間よく混錬した。その後直ちにアミン化合物(F)として1,8−ジアザビシクロ[5.4.0]−7−ウンデセン0.7質量部を量りとり、得られた混練物に加え、さらに1分間よく混錬した。混練終了時間を硬化開始時間とし、金属缶を23℃、50%RHの条件下に静置した。スパチュラで、金属缶中の組成物の一部を練り、粘性液状からゴム弾性体となり始めるまでの時間をゲル化時間として硬化性を評価したところ、ゲル化時間は15分であった。なお、本実施例の硬化性組成物において、フッ化水素アンモニウムのモル数に対する、アミン化合物(F)のモル数の比は、1.0である。
表17に示した重量比でフッ化塩化合物(B)として、テトラブチルアンモニウムフルオライド−THF溶液(1M溶液)(Aldrich(株)製)、プロトン酸(D)としてバーサチック酸(ジャパン エポキシ レジン(株)製)、スルホニル基を有する化合物(E)(富士アミドケミカル製)を加え、60℃、0.1気圧下で減圧脱揮を1時間行い、混合触媒を得た。
フッ化アンモニウムを乳鉢で粉砕した後、目開き150μmのふるいを通した。これに表18に示す処方に従って分散剤(H)、アミン化合物(F)、酸化合物(G)を加えてスパチュラでよく混合し、得られたペースト状物をそのまま触媒組成物とした。以下、実施例84〜96の触媒組成物を、それぞれ触媒組成物84〜96と称する。
表19に示す処方に従ってアミン化合物(F)、酸化合物(G)を混合し、得られた組成物を比較触媒組成物20、21とした。
23℃、50%RHの条件下、表20に示す処方に従って金属缶中に各成分を量りとり、スパチュラを用いて1分間よく混錬し硬化性組成物とした。混練終了時間を硬化開始時間とし、金属缶を23℃、50%RHの条件下に静置した。スパチュラで組成物の一部を練り粘性液状からゴム弾性体となり始めるまでの時間をゲル化時間として硬化性を評価した。結果を表20に示す。
表21に示す処方に従って実施例97〜111と同様に硬化性を評価した。結果を表21に示す。
反応性ケイ素基を有する重合体(A)として合成例2で得られた重合体(A−2)100重量部、充填剤(C)として表面処理膠質炭酸カルシウム(白石工業(株)製、商品名:白艶華CCR)120重量部、および酸化チタン(石原産業(株)製、商品名:タイペークR−820)20重量部を使用し、さらに、可塑剤(三井化学ポリウレタン(株)製、商品名:アクトコールP23)55重量部、チクソ性付与剤(楠本化成(株)製、商品名:ディスパロン#6500)2重量部、酸化防止剤((株)ワイ・エス・ケー製、商品名:ユノックスKC)1重量部、紫外線吸収剤(チバ・スペシャルティ・ケミカルズ(株)製、商品名:チヌビン327)1重量部、光安定剤(三共(株)製、商品名:サノールLS770)1重量部を使用し、各々計量、混合して充分混練りした後、3本ペイントロールを用いて分散させた。接着付与剤としてγ−(2−アミノエチル)アミノプロピルトリメトキシシラン(東レ・ダウコーニング(株)製、商品名:A−1120)3重量部、反応性ケイ素基を有する化合物としてビニルトリメトキシシラン(東レ・ダウコーニング(株)製、商品名:A−171)2重量部を加えて混練して主剤とした。
23℃、50%RHの条件下、金属缶中に、反応性ケイ素基を有する重合体(A)として合成例2で得られた重合体(A−2)100重量部、および実施例84〜96で用いた粒径150μm以下のフッ化水素アンモニウム1.0重量部、アミン化合物(F)として3−ジエチルアミノプロピルアミン3.7重量部、酸化合物(G)としてネオデカン酸4.6重量部を量りとり、スパチュラを用いて1分間よく混錬した。(フッ化アンモニウムのモル数に対する、3−ジエチルアミノプロピルアミンのモル数の比は1.0であり、アミン化合物(F)のモル数に対する酸化合物(G)のモル数の比は1.0である。)混練終了時間を硬化開始時間とし、金属缶を23℃、50%RHの条件下に静置した。スパチュラで組成物の一部を練り粘性液状からゴム弾性体となり始めるまでの時間をゲル化時間として硬化性を評価したところ、ゲル化時間は40分であった。
Claims (34)
- シロキサン結合を形成することにより架橋し得るケイ素含有基を有する重合体(A)と、フッ化塩化合物(B)と、アミン化合物(F)とを含む硬化性組成物であって、
前記フッ化塩化合物(B)が、以下のフッ化塩化合物(B1)である硬化性組成物。
フッ化塩化合物(B1):フッ化置換アンモニウム塩あるいはフッ化非置換アンモニウム塩であって、該フッ化置換アンモニウム塩で置換基が炭化水素基の場合あるいは該フッ化非置換アンモニウム塩の場合には、前記フッ化塩化合物(B)は一般式(1):
R4−mNHmF・(HF)n
(式中Rは置換あるいは非置換の炭化水素基、0≦m≦4、nは0または正の数を表し、mおよびnが同時に0となることはない)で表されるフッ化塩化合物。 - 前記フッ化塩化合物(B1)がアンモニウムハイドロフルオライド化合物(B2)である請求項1に記載の硬化性組成物。
- 前記フッ化塩化合物(B1)が1級、2級、あるいは3級のフッ化置換アンモニウム塩化合物(B3)である請求項1または2に記載の硬化性組成物。
- 前記フッ化塩化合物(B)の最大粒子径が150μm以下である請求項1〜3のいずれかに記載の硬化性組成物。
- 前記アミン化合物(F)がアミジン化合物である請求項1〜5のいずれか1項に記載の硬化性組成物。
- 前記アミン化合物(F)がアミノ基を有する3級アミン化合物である請求項1〜5のいずれか1項に記載の硬化性組成物。
- 前記フッ化塩化合物(B)の合計モル数に対する、前記アミン化合物(F)の合計モル数の比が0.1〜10である請求項1〜7のいずれか1項に記載の硬化性組成物。
- 酸化合物(G)をさらに含む請求項1〜8のいずれかに記載の硬化性組成物。
- 前記酸化合物(G)がカルボン酸である請求項9に記載の硬化性組成物。
- 前記アミン化合物(F)の合計モル数に対する前記酸化合物(G)の合計モル数の比が0.5〜2である請求項10に記載の硬化性組成物。
- 前記酸化合物(G)が、カルボン酸無水物である請求項9に記載の硬化性組成物。
- 前記アミン化合物(F)のモル数に対する前記酸化合物(G)中のカルボン酸無水物基のモル数が0.1〜1である請求項12に記載の硬化性組成物。
- 充填剤(C)をさらに含む請求項1〜13のいずれかに記載の硬化性組成物であって、前記充填剤(C)が、脂肪酸以外で表面処理された沈降炭酸カルシウム、脂肪酸で表面処理された沈降炭酸カルシウム(前記フッ化塩化合物(B)中に含有されるフッ素原子と、前記脂肪酸で表面処理された沈降炭酸カルシウムとの重量比が0.0015以上を満たす。)、重質炭酸カルシウムおよびシリカからなる群より選択される少なくとも1種以上である硬化性組成物。
- プロトン酸(D)をさらに含む請求項1〜14のいずれか1項に記載の硬化性組成物。
- 前記プロトン酸(D)は、脂肪酸である請求項15に記載の硬化性組成物。
- 前記プロトン酸(D)は、スルホン酸である請求項15に記載の硬化性組成物。
- 前記プロトン酸(D)が供与し得るH+イオンのモル数と、前記フッ化塩化合物(B)中のフッ素原子のモル数との比が0.1以上である請求項15〜17のいずれか1項に記載の硬化性組成物。
- スルホン酸以外のスルホニル基を有する化合物(E)を更に含む請求項1〜18のいずれに記載の硬化性組成物。
- 前記スルホニル基を有する化合物(E)のモル数と、フッ化塩化合物(B)のフッ素原子のモル数との比が0.5以上である請求項19に記載の硬化性組成物。
- 前記重合体(A)100重量部に対して、0.001〜30重量部の前記フッ化塩化合物(B)を含有する請求項1〜20のいずれかに記載の硬化性組成物。
- 前記重合体(A)100重量部に対して、5〜500重量部の前記充填剤(C)を含有する請求項14〜21のいずれかに記載の硬化性組成物。
- 前記重合体(A)は、シロキサン結合を形成することにより架橋し得るケイ素含有基を1分子あたり平均して1個以上有する重合体である請求項1〜22のいずれかに記載の硬化性組成物。
- 前記重合体(A)が有するシロキサン結合を形成することにより架橋し得るケイ素含有基が、下記一般式(3):
−SiR1 3−aXa (3)
(式中、(3−a)個のR1は、それぞれ独立に、炭素原子数1から20の炭化水素基あるいはR2 3SiO−(3個のR2はそれぞれ独立に、炭素原子数1から20の炭化水素基である。)で示されるシロキシ基であり、a個のXはそれぞれ独立に、水酸基、アルコキシ基、アルケニルオキシ基、アシルオキシ基、フェノキシ基からなる群より選択される基である。また、aは1,2,3のいずれかである。)で表される請求項1〜23のいずれかに記載の硬化性組成物。 - 一般式(3)中に記載のaが2である請求項24に記載の硬化性組成物。
- 一般式(3)中に記載のXがアルコキシ基である請求項24または25に記載の硬化性組成物。
- 前記重合体(A)の数平均分子量が3,000〜100,000である請求項1〜26のいずれかに記載の硬化性組成物。
- 前記重合体(A)は、ポリオキシアルキレン系重合体、飽和炭化水素系重合体、および(メタ)アクリル酸エステル系重合体からなる群から選択される少なくとも1種の主鎖骨格を有する重合体である、請求項1〜27のいずれかに記載の硬化性組成物。
- 請求項1〜28のいずれかに記載の硬化性組成物を用いてなるシーリング材。
- 請求項1〜28のいずれか1項に記載の硬化性組成物を用いてなる接着剤。
- フッ化塩化合物(B)と、アミン化合物(F)と、を含む、シロキサン結合を形成することにより架橋し得るケイ素含有基を有する重合体(A)の硬化のために用いられる触媒組成物。
- 前記酸化合物(G)をさらに含む請求項31に記載の触媒組成物。
- 分散剤(H)をさらに含む請求項31または32に記載の触媒組成物。
- シロキサン結合を形成することにより架橋し得るケイ素含有基を有する重合体(A)と、請求項31〜33のいずれかに記載の触媒組成物と、を含む硬化性組成物。
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JP7046830B2 (ja) | 2016-12-07 | 2022-04-04 | 株式会社カネカ | 液状樹脂組成物 |
JP2021507023A (ja) * | 2017-12-14 | 2021-02-22 | ボスティク エス.アー. | 接着性多成分組成物およびその使用 |
JP7418329B2 (ja) | 2017-12-14 | 2024-01-19 | ボスティク エス アー | 接着性多成分組成物およびその使用 |
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EP2088173A1 (en) | 2009-08-12 |
US9051501B2 (en) | 2015-06-09 |
WO2008062866A1 (fr) | 2008-05-29 |
EP2302000B1 (en) | 2016-11-16 |
EP2088173A4 (en) | 2010-06-23 |
EP2302000A1 (en) | 2011-03-30 |
ATE546492T1 (de) | 2012-03-15 |
JP5258575B2 (ja) | 2013-08-07 |
US20100041810A1 (en) | 2010-02-18 |
EP2088173B1 (en) | 2012-02-22 |
JP5767192B2 (ja) | 2015-08-19 |
JPWO2008062866A1 (ja) | 2010-03-04 |
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