JP5449508B2 - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
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- JP5449508B2 JP5449508B2 JP2012246502A JP2012246502A JP5449508B2 JP 5449508 B2 JP5449508 B2 JP 5449508B2 JP 2012246502 A JP2012246502 A JP 2012246502A JP 2012246502 A JP2012246502 A JP 2012246502A JP 5449508 B2 JP5449508 B2 JP 5449508B2
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- polymer
- compound
- reactive silicon
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- 239000001993 wax Substances 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 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
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Description
(I).シロキサン結合を形成することにより架橋し得る反応性ケイ素基を、1分子あたり、平均して1個以上有する重合体(A)、
ルイス酸および/またはその誘導体(B)、
アミン化合物(C)、
一般式(1):−SiR1 3−aXa (1)
(式中、(3−a)個のR1は、それぞれ独立に、炭素原子数1から20の炭化水素基である。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からなる群より選択される少なくとも1つである。また、aは1,2,3のいずれかである。)で示される反応性ケイ素基を有する化合物(D)、
充填剤(E)、
を構成成分とし、各成分を混合して得られる硬化性組成物、
(II).重合体(A)中に存在する反応性ケイ素基が、
一般式(2):−SiR3 3−bYb (2)
(式中、(3−b)個のR3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。b個のY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からなる群より選択される少なくとも1つである。また、bは1,2,3のいずれかである。)で示される反応性ケイ素基であることを特徴とする(I)に記載の硬化性組成物、
(III).一般式(2)中に記載のbが2であることを特徴とする(II)に記載の硬化性組成物、
(IV).反応性ケイ素基を有する重合体(A)が、数平均分子量が3,000〜100,000の重合体であることを特徴とする(I)〜(III)のいずれか1項に記載の硬化性組成物、
(V).反応性ケイ素基を有する重合体(A)の主鎖骨格が、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種であることを特徴とする(I)〜(IV)のいずれか1項に記載の硬化性組成物、
(VI).一般式(2)中に記載のYがアルコキシ基であることを特徴とする(II)〜(V)のいずれか1項に記載の硬化性組成物、
(VII).一般式(2)中に記載のYがメトキシ基であることを特徴とする(II)〜(V)のいずれか1項に記載の硬化性組成物、
(VIII).ルイス酸および/またはその誘導体(B)がBF3および/またはその錯体であることを特徴とする(I)〜(VII)のいずれか1項に記載の硬化性組成物、
(IX).アミン化合物(C)がアリール置換グアニジン化合物および/またはアリール置換ビグアニド化合物であることを特徴とする(I)〜(VIII)のいずれか1項に記載の硬化性組成物、
(X).一般式(1)中に記載のaが3であることを特徴とする(I)〜(IX)のいずれか1項に記載の硬化性組成物、
(XI).反応性ケイ素基を有する化合物(D)の分子量が3,000以下であることを特徴とする(I)〜(X)のいずれか1項に記載の硬化性組成物、
(XII).一般式(1)中に記載のXがアルコキシ基であることを特徴とする(I)〜(XI)のいずれか1項に記載の硬化性組成物、
(XIII).反応性ケイ素基を有する化合物(D)中に存在する(一般式(1)中に記載の)Xの量が平均して5mmol/g以上であることを特徴とする(I)〜(XII)のいずれか1項に記載の硬化性組成物、
(XIV).充填剤(E)が脂肪酸および/または脂肪酸塩で表面処理された沈降炭酸カルシウムであることを特徴とする(I)〜(XIII)のいずれか1項に記載の硬化性組成物、
(XV).少なくとも反応性ケイ素基を有する重合体(A)および/または反応性ケイ素基を有する化合物(D)と、ルイス酸および/またはその誘導体(B)とを含む成分をあらかじめ混合したのち、これと、少なくとも充填剤(E)を含むその他成分とを混合してなることを特徴とする(I)〜(XIV)のいずれか1項に記載の硬化性組成物、
(XVI).少なくとも反応性ケイ素基を有する重合体(A)および/または反応性ケイ素基を有する化合物(D)と、ルイス酸および/またはその誘導体(B)とを含む成分を充填剤(E)が存在しない条件であらかじめ混合したのち、これと、少なくとも充填剤(E)を含むその他成分とを混合してなることを特徴とする(XV)に記載の硬化性組成物、
(XVII).少なくとも反応性ケイ素基を有する重合体(A)および充填剤(E)を含む成分をあらかじめ混合したのち、これと、少なくともルイス酸および/またはその誘導体(B)を含むその他成分とを混合してなることを特徴とする(I)〜(XIV)のいずれか1項に記載の硬化性組成物、
(XVIII).硬化性組成物を40℃以上の温度で加熱する工程を含む工程で製造されたことを特徴とする(I)〜(XVII)のいずれか1項に記載の硬化性組成物、
(XIX).(I)〜(XVIII)のいずれか1項に記載の硬化性組成物を用いてなるシーリング材、
(XX).(I)〜(XVIII)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、
に関する。
重合体(A)は、反応性ケイ素基を1分子あたり平均して1個以上有する。ここで、反応性ケイ素基とは、ケイ素原子に結合した水酸基又は加水分解性基を有する有機基である。反応性ケイ素基を有する重合体(A)は、シラノール縮合触媒によって加速される反応によりシロキサン結合が形成され、架橋する特徴を有する。
反応性ケイ素基としては、たとえば
−SiR3 3−bYb (2)
(式中、(3−b)個のR3は、それぞれ独立に、炭素原子数1から20の炭化水素基であり、b個のY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からなる群より選択される少なくとも1つである。また、bは1,2,3のいずれかである。)で示されるケイ素基があげられる。
一般式(3):
−R4−O− (3)
(R4は炭素原子数1から14の直鎖状もしくは分岐状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。
(メタ)アクリル酸エステル系重合体には、(メタ)アクリル酸エステル化合物と、これと共重合可能なビニル化合物の共重合体を含む。
(メタ)アクリル酸エステル化合物と共重合可能なビニル化合物としては、特に限定されず、たとえば、スチレン、ビニルトルエン、α−メチルスチレン、クロルスチレン、スチレンスルホン酸及びその塩などのスチレン系化合物;ビニルトリメトキシシラン、ビニルトリエトキシシランなどのケイ素を有するビニル系化合物;無水マレイン酸、マレイン酸、マレイン酸のモノアルキルエステル類及びジアルキルエステル類;フマル酸、フマル酸のモノアルキルエステル類及びジアルキルエステル類;マレイミド、メチルマレイミド、エチルマレイミド、プロピルマレイミド、ブチルマレイミド、ヘキシルマレイミド、オクチルマレイミド、ドデシルマレイミド、ステアリルマレイミド、フェニルマレイミド、シクロヘキシルマレイミドなどのマレイミド系化合物;アクリロニトリル、メタクリロニトリルなどのニトリル基を有するビニル系化合物;アクリルアミド、メタクリルアミドなどのアミド基を有するビニル系化合物;酢酸ビニル、プロピオン酸ビニル、ピバリン酸ビニル、安息香酸ビニル、桂皮酸ビニルなどのビニルエステル類;エチレン、プロピレンなどのアルケン類;ブタジエン、イソプレンなどの共役ジエン類;塩化ビニル、塩化ビニリデン、塩化アリル、アリルアルコールなどがあげられ、これらは、複数を共重合成分として使用することも可能である。
(メタ)アクリル酸エステル系重合体の製造方法としては、特に限定されず、公知の方法があげられる。このなかでも、高い割合で分子鎖末端に架橋性官能基を導入しやすいこと、分子量分布が狭く、低粘度の重合体が得られることなどから、リビングラジカル重合法を用いることが好ましい。なお、重合開始剤としてアゾ系化合物、過酸化物などを用いる通常のフリーラジカル重合法で得られる重合体は、分子量分布の値が一般に2以上と大きく、粘度が高くなる傾向がある。
−CH2−C(R5)(COOR6)− (4)
(式中、R5は水素原子またはメチル基、R6は炭素原子数1から8のアルキル基を示す)で示される炭素原子数1から8のアルキル基を有する繰り返し単位と、
一般式(5):
−CH2−C(R5)(COOR7)− (5)
(式中、R5は一般式(4)記載の表記に同じ、R7は炭素原子数9以上のアルキル基を示す。)で示される炭素原子数9以上のアルキル基を有する繰り返し単位とからなる共重合体があげられる。
(メタ)アクリル酸エステル系共重合体は実質的に一般式(4)及び一般式(5)記載の繰り返し単位から構成される。ここで、「実質的に」とは共重合体中に占める、一般式(4)、(5)記載の繰り返し単位の合計量の割合が50重量%をこえることを意味し、共重合体に占める一般式(4)、(5)記載の繰り返し単位の合計量の割合は70重量%以上が好ましい。
(メタ)アクリル酸エステル系共重合体は、一般式(4)、(5)の繰り返し単位として使用される(メタ)アクリル酸エステル系化合物と、これと共重合可能なビニル化合物の共重合体を含む。
−NR8−C(=O)− (6)
(R8は水素原子または有機基を表す。)で示される有機基をいう。
U−R9−SiR3 3−bZb (7)
(式中、(3−b)個のR3は一般式(2)の表記と同じ。bは1,2,3のいずれかである。R9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2価の炭化水素基である。b個のZは水酸基または加水分解性基である。Uは水酸基、カルボキシル基、メルカプト基およびアミノ基(1級または2級)からなる群より選択される、少なくとも1つの活性水素を有する基である。)で示されるケイ素化合物中のUを反応させる方法があげられる。
O=C=N−R9−SiR3 3−bZb (8)
(ただし、式中R9、(3−b)個のR3、b個のZ、bは、一般式(7)の表記と同じ。)で示される反応性ケイ素基を有するイソシアネート化合物のイソシアネート基を反応させる方法があげられる。
−(SiR10 2−cYcO)l−SiR3 3−bYb (2−1)
(式中、R3およびR10は、それぞれ独立に、炭素原子数1から20の置換あるいは非置換の炭化水素基を示し、Yはそれぞれ独立にR2 3SiO−(R2はそれぞれ独立に、炭素原子数1から20の置換あるいは非置換の炭化水素基である)で示されるシロキシ基、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、あるいはフェノキシ基を示す。また、bは1,2,3のいずれかであり、cは0,1,2のいずれかであり、lは0または1〜19の整数である)で示される反応性ケイ素基を用いることもできる。
(イ)分子中に水酸基などの官能基を有する重合体に、この官能基に対して反応性を示す活性基および不飽和基を有する有機化合物を反応させ、不飽和基を有する重合体を得る。もしくは、不飽和基を有するエポキシ化合物との共重合により不飽和基を有する重合体を得る。ついで得られた反応生成物に反応性ケイ素基を有するヒドロシランを作用させてヒドロシリル化する方法。
(ロ)(イ)の方法と同様にして得られた不飽和基を有する有機重合体にメルカプト基および反応性ケイ素基を有する化合物を反応させる方法。
(ハ)分子中に水酸基、エポキシ基やイソシアネート基などの官能基を有する有機重合体に、この官能基に対して反応性を示す官能基および反応性ケイ素基を有する化合物を反応させる方法。
(イ)の方法において使用されるヒドロシラン化合物としては、特に限定されず、たとえば、トリクロロシラン、メチルジクロロシラン、ジメチルクロロシラン、フェニルジクロロシランなどのハロゲン化ヒドロシラン類;トリメトキシシラン、トリエトキシシラン、メチルジエトキシシラン、メチルジメトキシシラン、フェニルジメトキシシラン、1−[2−(トリメトキシシリル)エチル]−1,1,3,3−テトラメチルジシロキサンのようなアルコキシシラン類;メチルジアセトキシシラン、フェニルジアセトキシシランなどのアシロキシヒドロシラン類;ビス(ジメチルケトキシメート)メチルシラン、ビス(シクロヘキシルケトキシメート)メチルシランなどのケトキシメートヒドロシラン類などがあげられる。これらのなかでは、ハロゲン化ヒドロシラン類、アルコキシヒドロシラン類が好ましく、得られる重合体(A)を主成分とする硬化性組成物が、加水分解性が穏やかで取り扱いやすいことから、アルコキシヒドロシラン類がより好ましい。前記アルコキシヒドロシラン類の中でも、入手が容易なこと、得られる重合体(A)を主成分とする硬化性組成物および硬化物の諸特性(硬化性、貯蔵安定性、伸び特性、引張強度など)が優れることから、メチルジメトキシシランが好ましい。
H−SiY3 (9)
(式中、Yは一般式(2)の表記と同じ。)で示されるヒドロシラン化合物は、付加反応により得られる重合体(A)を主成分とする硬化性組成物が、優れた硬化性を有することより好ましい。一般式(9)記載のヒドロシラン化合物の中でも、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などのトリアルコキシシラン類がより好ましい。
H−Si(OR11)3 (10)
(式中、3個のR11は、それぞれ独立に炭素原子数2から20の有機基である)で示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。また、入手が容易なこと、取り扱いの際の安全性が高いことから、トリエトキシシランがより好ましい。
(ロ)の合成方法としては、特に限定されず、たとえば、メルカプト基および反応性ケイ素基を有する化合物を、ラジカル開始剤および/またはラジカル発生源存在下でのラジカル付加反応によって、有機重合体の不飽和結合部位に導入する方法などがあげられる。メルカプト基および反応性ケイ素基を有する化合物としては、特に限定されず、たとえば、γ−メルカプトプロピルトリメトキシシラン、γ−メルカプトプロピルメチルジメトキシシラン、γ−メルカプトプロピルトリエトキシシラン、γ−メルカプトプロピルメチルジエトキシシラン、メルカプトメチルトリメトキシシラン、メルカプトメチルトリエトキシシランなどがあげられる。
(ハ)の合成方法のなかで末端に水酸基を有する重合体とイソシアネート基および反応性ケイ素基を有する化合物を反応させる方法としては、特に限定されず、たとえば、特開平3−47825号公報に開示される方法などがあげられる。イソシアネート基および反応性ケイ素基を有する化合物としては、特に限定されず、たとえば、γ−イソシアネートプロピルトリメトキシシラン、γ−イソシアネートプロピルメチルジメトキシシラン、γ−イソシアネートプロピルトリエトキシシラン、γ−イソシアネートプロピルメチルジエトキシシラン、イソシアネートメチルトリメトキシシラン、イソシアネートメチルトリエトキシシラン、イソシアネートメチルジメトキシメチルシラン、イソシアネートメチルジエトキシメチルシランなどがあげられる。
H−(SiR12 2O)mSiR12 2−R13−SiX2 3 (11)
(式中、3個のX2はそれぞれ独立に水酸基、または加水分解性基である。(2m+2)個のR12は、それぞれ独立に、炭化水素基であり、入手性およびコストの点から、炭素原子数1から20の炭化水素基が好ましく、炭素原子数1から8の炭化水素基がより好ましく、炭素原子数1から4の炭化水素基が特に好ましい。R13は2価の有機基であり、入手性およびコストの点から、炭素原子数1から12の2価の炭化水素基が好ましく、炭素原子数2から8の2価の炭化水素基がより好ましく、炭素原子数2の2価の炭化水素基が特に好ましい。また、mは、0から19の整数であり、入手性およびコストの点から、1が好ましい。)で示されるシラン化合物は、不均化反応が進まない。このため、(イ)の合成法で、1つのケイ素原子に3個の加水分解性基が結合している基を導入する場合には、一般式(11)で示されるシラン化合物を用いることが好ましい。
−SiR1 3−aXa (1)
(式中、R1は、それぞれ独立に、置換あるいは非置換の炭素原子数1から20の炭化水素基を示し、Y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、あるいはフェノキシ基あるいはR2 3SiO−(R2はそれぞれ独立に、炭素原子数1から20の置換あるいは非置換の炭化水素基である)で示されるシロキシ基からなる群より選択される少なくとも1つである。また、aは1,2,3のいずれかである。)で示されるケイ素基を有する化合物であり、ルイス酸および/またはその誘導体(B)と反応して硬化触媒となりうるものである。
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(重量比)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い、数平均分子量約19,000(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。
表1に示す処方に従って、反応性ケイ素基を有する重合体(A)として合成例1で得られた重合体(A1)と、充填剤(E)として表1に示す充填剤、およびその他の成分として可塑剤、チクソ性付与剤とを混合し、3本ペイントロールで混練して主剤1とした。
23℃、50%RHの条件下、表3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。混練終了時点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。
(実施例3、4)
23℃、50%RHの条件下、表4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。混練終了時点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るまでの時間をゲル化時間として硬化時間を測定した。結果を表4に示す。
表5に示す処方に従って、反応性ケイ素基を有する重合体(A)として合成例1で得られた重合体(A1)、充填剤(E)として表5に示す充填剤、およびその他の成分として可塑剤、チクソ性付与剤とを混合し、3本ペイントロールで混練して主剤2とした。
表1に示す主剤1を用い、表7に示す処方に従って、酸化防止剤、紫外線吸収剤、光安定剤、反応性ケイ素基を有する化合物(D)を混合して主剤3とした。
ガラス容器中、室温にて反応性ケイ素基を有する化合物(D)としてビニルトリメトキシシラン100重量部と、ルイス酸および/またはその誘導体(B)としてBF3のジエチルエーテル錯体35重量部を量りとり攪拌混合して組成物(BD4)を得た。
反応性ケイ素基を有する重合体(A)として合成例1で得られた重合体(A1)100重量部、充填剤(E)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)50.5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、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。この後、120℃で2時間減圧脱水を行い、50℃以下に冷却後、反応性ケイ素基を有する化合物(D)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重量部および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重量部を加えて混練し、さらにルイス酸および/またはその誘導体(B)としてBF3のジエチルエーテル錯体4重量部を加えて混練し、最後にアミン化合物(C)として1−フェニルグアニジン3重量部を可塑剤(武田薬品工業(株)製、商品名:アクトコールP23)4.5重量部に溶解したものを加えて実質的に水分の存在しない状態で混練し、防湿性の容器に密閉し、一液型硬化性組成物を得た。
反応性ケイ素基を有する重合体(A)として合成例1で得られた重合体(A1)100重量部、充填剤(E)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、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。この後、120℃で2時間減圧脱水を行い、50℃以下に冷却後、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、ルイス酸および/またはその誘導体(B)と反応性ケイ素基を有する化合物(D)とを混合して得られた組成物として実施例14で用いた(BD4)7重量部、アミン化合物(C)として1−フェニルグアニジンの50重量%メタノール溶液10重量部を加えて実質的に水分の存在しない状態で混練し、防湿性の容器に密閉し、一液型硬化性組成物を得た。
反応性ケイ素基を有する重合体(A)として合成例1で得られた重合体(A1)100重量部、充填剤(E)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、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。この後、120℃で2時間減圧脱水を行い、50℃以下に冷却後、反応性ケイ素基を有する化合物(D)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重量部および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重量部を加えて混練し、得られたものを主剤4とした。
反応性ケイ素基を有する重合体(A)として合成例1で得られた重合体(A1)100重量部、およびルイス酸および/またはその誘導体(B)としてBF3のジエチルエーテル錯体1重量部を加えて混合した後23℃にて10分間放置した。得られた混合物に、充填剤(E)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重量部を各々計量、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。得られた混合物に、反応性ケイ素基を有する化合物(D)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)10重量部を計量、混合し、さらにアミン化合物(C)としてDBU2重量部を計量、混合し硬化性組成物を得た。
Claims (17)
- シロキサン結合を形成することにより架橋し得る反応性ケイ素基を、1分子あたり、平均して1個以上有する重合体(A)、
ルイス酸および/またはその誘導体(B)、
アミン化合物(C)、
一般式(1):−SiR1 3−aXa (1)
(式中、(3−a)個のR1は、それぞれ独立に、炭素原子数1から20の炭化水素基である。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からなる群より選択される少なくとも1つである。また、aは1,2,3のいずれかである。)で示される反応性ケイ素基を有する化合物(D)、
充填剤(E)、
を構成成分とし、
少なくとも反応性ケイ素基を有する重合体(A)および充填剤(E)を含む成分をあらかじめ混合したのち、これと、少なくともルイス酸および/またはその誘導体(B)を含むその他成分とを混合してなることを特徴とする硬化性組成物。 - 重合体(A)中に存在する反応性ケイ素基が、
一般式(2):−SiR3 3−bYb (2)
(式中、(3−b)個のR3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。b個のY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からなる群より選択される少なくとも1つである。また、bは1,2,3のいずれかである。)で示される反応性ケイ素基であることを特徴とする請求項1に記載の硬化性組成物。 - 一般式(2)中に記載のbが2であることを特徴とする請求項2に記載の硬化性組成物。
- 反応性ケイ素基を有する重合体(A)が、数平均分子量が3,000〜100,000の重合体であることを特徴とする請求項1〜3のいずれか1項に記載の硬化性組成物。
- 反応性ケイ素基を有する重合体(A)の主鎖骨格が、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種であることを特徴とする請求項1〜4のいずれか1項に記載の硬化性組成物。
- 一般式(2)中に記載のYがアルコキシ基であることを特徴とする請求項2〜5のいずれか1項に記載の硬化性組成物。
- 一般式(2)中に記載のYがメトキシ基であることを特徴とする請求項2〜5のいずれか1項に記載の硬化性組成物。
- ルイス酸および/またはその誘導体(B)がBF3および/またはその錯体であることを特徴とする請求項1〜7のいずれか1項に記載の硬化性組成物。
- アミン化合物(C)がアリール置換グアニジン化合物および/またはアリール置換ビグアニド化合物であることを特徴とする請求項1〜8のいずれか1項に記載の硬化性組成物。
- 一般式(1)中に記載のaが3であることを特徴とする請求項1〜9のいずれか1項に記載の硬化性組成物。
- 反応性ケイ素基を有する化合物(D)の分子量が3,000以下であることを特徴とする請求項1〜10のいずれか1項に記載の硬化性組成物。
- 一般式(1)中に記載のXがアルコキシ基であることを特徴とする請求項1〜11のいずれか1項に記載の硬化性組成物。
- 反応性ケイ素基を有する化合物(D)中に存在する(一般式(1)中に記載の)Xの量が平均して5mmol/g以上であることを特徴とする請求項1〜12のいずれか1項に記載の硬化性組成物。
- 充填剤(E)が脂肪酸および/または脂肪酸塩で表面処理された沈降炭酸カルシウムであることを特徴とする請求項1〜13のいずれか1項に記載の硬化性組成物。
- 硬化性組成物を40℃以上の温度で加熱する工程を含む工程で製造されたことを特徴する請求項1〜14のいずれか1項に記載の硬化性組成物。
- 請求項1〜15のいずれか1項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1〜15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。
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WO2008099858A1 (ja) | 2008-08-21 |
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US20130116378A1 (en) | 2013-05-09 |
US20100152373A1 (en) | 2010-06-17 |
JP5281901B2 (ja) | 2013-09-04 |
US8962716B2 (en) | 2015-02-24 |
US8815985B2 (en) | 2014-08-26 |
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