JP5349959B2 - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
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- JP5349959B2 JP5349959B2 JP2008512141A JP2008512141A JP5349959B2 JP 5349959 B2 JP5349959 B2 JP 5349959B2 JP 2008512141 A JP2008512141 A JP 2008512141A JP 2008512141 A JP2008512141 A JP 2008512141A JP 5349959 B2 JP5349959 B2 JP 5349959B2
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- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- XSIGLRIVXRKQRA-UHFFFAOYSA-N triethoxysilylmethanethiol Chemical compound CCO[Si](CS)(OCC)OCC XSIGLRIVXRKQRA-UHFFFAOYSA-N 0.000 description 1
- QVMRVWAOMIXFFW-UHFFFAOYSA-N triethyl(fluoro)silane Chemical compound CC[Si](F)(CC)CC QVMRVWAOMIXFFW-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- KGWNTHHPMKEAIK-UHFFFAOYSA-N trifluoro(phenyl)silane Chemical compound F[Si](F)(F)C1=CC=CC=C1 KGWNTHHPMKEAIK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- IXSPLXSQNNZJJU-UHFFFAOYSA-N trimethyl(silyloxy)silane Chemical compound C[Si](C)(C)O[SiH3] IXSPLXSQNNZJJU-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 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
- 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).(A)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基を有する重合体、
(B)一般式(1):
R1 4−aSiFa (1)
(式中、4−a個の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、または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またはフッ素原子である。)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。)で示されるフルオロシラン類、
(C)アミン系化合物、を含むことを特徴とする硬化性組成物、
(II).(A)成分が、数平均分子量3,000〜100,000の重合体であり、且つ、一般式(2):
−(SiR4 2−cZcO)l−SiR3 3−bZb (2)
(式中、R3およびR4は、それぞれ独立に、炭素原子数1から20の炭化水素基、またはR5 3SiO−(R5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)で示されるトリオルガノ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、Zは、それぞれ独立に、水酸基または加水分解性基である。さらに、bは0、1、2、3のいずれかであり、cは0、1、2のいずれかであり、bとcとが同時に0になることはない。また、lは0または1〜19の整数である。)で示されるケイ素基を、1分子あたり、平均して1個以上有することを特徴とする(I)に記載の硬化性組成物、
(III).(A)成分の重合体の主鎖骨格が、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より選択される少なくとも1種であることを特徴とする (I) または (II) に記載の硬化性組成物、
(IV).Zがアルコキシ基であることを特徴とする(II)または(III)に記載の硬化性組成物、
(V).アルコキシ基がメトキシ基であることを特徴とする(IV)に記載の硬化性組成物、
(VI).(B)成分が分子量3,000以下のフルオロシラン類であることを特徴とする (I) 〜 (V) のいずれかに記載の硬化性組成物、
(VII). (I) 〜 (VI) 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、
(VIII). (I) 〜 (VI) のいずれかに記載の硬化性組成物を用いてなる接着剤、
に関する。
−(SiR4 2−cZcO)l−SiR3 3−bZb (2)
(式中、R3およびR4は、それぞれ独立に、炭素原子数1から20の炭化水素基、またはR5 3SiO−(R5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)で示されるトリオルガノ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、Zは、それぞれ独立に、水酸基または加水分解性基である。さらに、bは0、1、2、3のいずれかであり、cは0、1、2のいずれかであり、bとcとが同時に0になることはない。また、lは0または1〜19の整数である。)で示される基が挙げられる。
−SiR3 3−dZd (3)
(式中、R3、Zは一般式(2)の表記と同じ。dは1、2または3を示す。)で示される反応性ケイ素基が、入手が容易であることから好ましい。
(ロ)(イ)法と同様にして得られた不飽和基を有する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等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、などが挙げられる。
H−SiZ3 (4)
(式中、Zは一般式(2)中の表記と同じ。)で示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重合体を主成分とす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)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等のトリアルコキシシラン類がより好ましい。
H−Si(OR6)3 (5)
(式中、3個のR6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。これらのなかでも入手が容易なこと、取り扱いの際の安全性が高いことなどから、トリエトキシシランが最も好ましい。
−R7−O− (6)
(式中、R7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り、一般式(6)におけるR7は、炭素原子数1から14の、さらには2から4の、直鎖状もしくは分岐状アルキレン基が好ましい。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(R8)(COOR9)− (7)
(式中、R8は水素原子またはメチル基、R9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(R8)(COOR10)− (8)
(式中、R8は前記に同じ、R10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。
−NR11C(=O)− (9)
(R11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。
U−R12−SiR3 3−dZd (10)
(ただし、式中、R3、Z、dは前記と同じ。R12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の置換あるいは非置換の2価の炭化水素基である。U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を有する基である。)で表されるケイ素化合物のU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、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−R12−SiR3 3−dZd (11)
(ただし、式中R3、R12、Z、dは前記に同じ。)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、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。
R1 4−aSiFa (1)
(式中、(4−a)個のR1はそれぞれ独立に、置換あるいは非置換の炭素原子1から20の炭化水素基、または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またはフッ素原子である)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。)で示されるフルオロシラン類(B)とアミン系化合物(C)を必須成分とする。
本発明の硬化性組成物中には、必要に応じて、接着性付与剤として、シランカップリング剤を添加できる。
本発明の硬化性組成物中には、必要に応じて、溶剤または希釈剤を添加することができる。溶剤及び希釈剤としては、特に限定されず、たとえば、脂肪族炭化水素類、芳香族炭化水素類、脂環族炭化水素類、ハロゲン化炭化水素類、アルコール類、エステル類、ケトン類、エーテル類などが挙げられる。これらは1週類のみを添加してもよく、複数種を組み合わせて添加してもよい。
このなかでもベンゾトリアゾール系紫外線吸収剤が好ましい。
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、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。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重量部に対し、n−ヘキサン300重量部と、水300重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重量部を混合攪拌し、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−1)を得た。
合成例1のトリメトキシシランをジメトキシメチルシラン0.9重量部とした以外は合成例1と同様の操作を行い、ジメトキシシリル基末端ポリオキシプロピレン系重合体(A−2)を得た。1H−NMRによる測定により、末端のジメトキシメチルシリル基は1分子あたり平均して約1.3個であった。
ミニカップに計り取った重合体(A−1,A−2)に、表1の処方に従って、先ずフルオロシラン(B)を添加し、すばやくスパチュラで1分間よく混錬し、次いでアミン系化合物(C)を添加し、さらに1分間混錬した。混錬後、カップを23℃50%の恒温恒湿室に静置し、この時間を硬化開始時間とした。始めの30分は1分毎、1時間までは10分毎、以降は1時間ごとにスパチュラの先で組成物表面に触り、スパチュラに組成物が付着しなくなるまでの時間を皮張り時間として、硬化時間を測定した。結果を表1に示す。
ビニル末端ポリジメチルシロキサン(DMSV42:Gelest社製)100重量部に対し、白金ビニルシロキサン錯体の白金含量3wt%のイソプロピルアルコール溶液150ppmを触媒として、下記化学式、
HSi(CH3)2OSi(CH3)2C2H4Si(OCH3)3
で表されるヒドロシラン化合物0.66重量部と90℃で2時間反応させ、トリメトキシシリル基末端ポリジメチルシロキサン(A−3)を得た。1H−NMRによる測定により、末端のトリメトキシシリル基は1分子あたり平均して約1.2個であった。
重合体(A−3)を用いて、表2に示す処方に従い、前記と同様の方法で硬化時間を測定した。結果を表2に示す。
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い、末端が水酸基である数平均分子量約26,000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。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重量部に対し、n−ヘキサン300重量部と、水300重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重量部を混合攪拌し、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−2)を得た。
表3に示す処方に従って、重合体(A−4)と充填剤、チクソ性付与剤を混練し主剤とした。
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14,500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。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重量部に対し、n−ヘキサン300重量部と、水300重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重量部を混合攪拌し、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14,500の2官能ポリプロピレンオキシド(P−3)を得た。
窒素雰囲気下、室温で、3−メタクリロキシプロピルジメトキシメチルシラン(LS−3375:信越化学工業(株)製)2.3gに、BF3ジエチルエーテル錯体(和光純薬工業(株)製)1.4gをゆっくりと滴下した。室温で2時間撹拌した後、真空脱揮により過剰のBF3エーテル錯体および反応副生成物を除去した。減圧蒸留により、3−メタクリロキシプロピルジフルオロメチルシラン(B−1)を得た。(B−1)の1H−NMRスペクトル(CDCl3):0.36ppm(3H)、0.85ppm(2H)、1.82ppm(2H)、1.95ppm(3H)、4.14ppm(2H)、5.57ppm(1H)、6.11ppm(1H)
(合成例7)
窒素雰囲気下、室温で、3−メタクリロキシプロピルトリメトキシシラン(LS−3380:信越化学工業(株)製)2.5gに、BF3ジエチルエーテル錯体2.1gをゆっくりと滴下した。室温で3時間撹拌した後、真空脱揮により過剰のBF3エーテル錯体および反応副生成物を除去した。減圧蒸留により、3−メタクリロキシプロピルトリフルオロシラン(B−2)を得た。(B−2)の1H−NMRスペクトル(CDCl3):1.09ppm(2H)、1.94ppm(5H)、4.17ppm(2H)、5.60ppm(1H)、6.12ppm(1H)
(合成例8)
窒素雰囲気下、室温で、オクタデシルメトキシジメチルシラン(SIO6618.0:Gelest,Inc製)3.4gに、BF3ジエチルエーテル錯体1.4gをゆっくりと滴下した。室温で1時間撹拌した後、真空脱揮により過剰のBF3エーテル錯体および反応副生成物を除去した。濾過により、オクタデシルフルオロジメチルシラン(B−3)を得た。(B−3)の1H−NMRスペクトル(CDCl3):0.21ppm(6H)、0.65ppm(2H)、0.88ppm(3H)、1.26ppm(32H)
(合成例9)
窒素雰囲気下、室温で、ジフェニルジメトキシシラン(AY43−047:東レ・ダウコーニング・シリコーン(株)製)2.4gに、BF3ジエチルエーテル錯体1.4gをゆっくりと滴下した。室温で12時間撹拌した後、真空脱揮により過剰のBF3エーテル錯体および反応副生成物を除去し、ジフェニルジフルオロシラン(B−4)を得た。(B−4)の1H−NMRスペクトル(CDCl3):7.47ppm(4H)、7.58ppm(2H)、7.73ppm(4H)
(合成例10)
窒素雰囲気下、室温で、ベンジルエトキシジメチルシラン(LS3950:信越化学工業(株)製)2.3gに、BF3ジエチルエーテル錯体1.4gをゆっくりと滴下した。室温で1時間撹拌した後、減圧脱揮により過剰のBF3エーテル錯体および反応副生成物を除去した。減圧蒸留によりベンジルフルオロジメチルシラン(B−5)を得た。(B−5)の1H−NMRスペクトル(CDCl3):0.22ppm(6H)、2.26ppm(2H)、7.07ppm(2H)、7.13ppm(1H)、7.25ppm(2H)
(実施例8〜12、比較例10〜12)
ミニカップに計り取った重合体(A−5)に、表4の処方に従って、先ずフルオロシラン類(B)を添加し、すばやくスパチュラで1分間よく混錬し、次いでアミン系化合物(C)を添加し、さらに1分間混錬した。混錬後、カップを23℃50%の恒温恒湿室に静置し、前記と同様にして、硬化時間を測定した。結果を表4に示す。
Claims (7)
- (A)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基を有する重合体、
(B)一般式(1):
R1 4−aSiFa (1)
(式中、4−a個の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、または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またはフッ素原子である。)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。)で示されるフルオロシラン類、
(C)アミン系化合物、を含み、
(A)成分が、数平均分子量3,000〜100,000の重合体であり、且つ、一般式(2):
−(SiR 4 2−c Z c O) l −SiR 3 3−b Z b (2)
(式中、R 3 およびR 4 は、それぞれ独立に、炭素原子数1から20の炭化水素基、またはR 5 3 SiO−(R 5 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)で示されるトリオルガノ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、Zは、それぞれ独立に、水酸基または加水分解性基である。さらに、bは0、1、2、3のいずれかであり、cは0、1、2のいずれかであり、bとcとが同時に0になることはない。また、lは0または1〜19の整数である。)で示されるケイ素基を、1分子あたり、平均して1個以上有し、
(A)成分の重合体の主鎖骨格が、ポリオキシアルキレン系重合体、飽和炭化水素系重合体、(メタ)アクリル酸エステル系重合体、およびポリシロキサン系重合体からなる群より選択される少なくとも1種であることを特徴とする硬化性組成物。 - (A)成分の重合体の主鎖骨格が、ポリオキシアルキレン系重合体およびポリシロキサン系重合体からなる群より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に記載の硬化性組成物。
- Zがアルコキシ基であることを特徴とする請求項1または2に記載の硬化性組成物。
- アルコキシ基がメトキシ基であることを特徴とする請求項3に記載の硬化性組成物。
- (B)成分が分子量3,000以下のフルオロシラン類であることを特徴とする請求項1〜4のいずれかに記載の硬化性組成物。
- 請求項1〜5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1〜5のいずれかに記載の硬化性組成物を用いてなる接着剤。
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US20090069505A1 (en) | 2009-03-12 |
EP2011834A1 (en) | 2009-01-07 |
US7772332B2 (en) | 2010-08-10 |
EP2011834B1 (en) | 2012-07-25 |
CN101426859A (zh) | 2009-05-06 |
EP2011834A4 (en) | 2010-07-14 |
WO2007123167A1 (ja) | 2007-11-01 |
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JPWO2007123167A1 (ja) | 2009-09-03 |
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