JP2011517707A - シリコーン組成物、シリコーン接着剤、塗装基板及び積層基板 - Google Patents
シリコーン組成物、シリコーン接着剤、塗装基板及び積層基板 Download PDFInfo
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- JP2011517707A JP2011517707A JP2010549719A JP2010549719A JP2011517707A JP 2011517707 A JP2011517707 A JP 2011517707A JP 2010549719 A JP2010549719 A JP 2010549719A JP 2010549719 A JP2010549719 A JP 2010549719A JP 2011517707 A JP2011517707 A JP 2011517707A
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- Prior art keywords
- substrate
- sio
- silicone
- organohydrogenpolysiloxane
- silicon
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 78
- 239000013464 silicone adhesive Substances 0.000 title claims abstract description 62
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 60
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims abstract description 71
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 17
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 16
- 238000000576 coating method Methods 0.000 claims description 63
- 239000011248 coating agent Substances 0.000 claims description 55
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- 230000001070 adhesive effect Effects 0.000 claims description 36
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- 125000003342 alkenyl group Chemical group 0.000 claims description 31
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- 239000011521 glass Substances 0.000 claims description 24
- 150000002894 organic compounds Chemical class 0.000 claims description 20
- 125000001183 hydrocarbyl group Chemical class 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 10
- 150000001282 organosilanes Chemical class 0.000 claims description 10
- 125000006657 (C1-C10) hydrocarbyl group Chemical group 0.000 claims description 8
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- 238000000034 method Methods 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
本出願は、米国特許法第119条(e)の下で、2008年3月4日に出願された米国仮特許出願第61/033447号の利益を主張する。米国仮特許出願第61/033447号は、参照により本明細書に援用される。
本発明は、シリコーン組成物に関し、より詳細には、1分子あたり平均少なくとも2つのケイ素結合水素原子を有する少なくとも1つのオルガノハイドロジェンポリシロキサンと、1分子あたり平均少なくとも2つの脂肪族炭素−炭素二重結合を有する架橋剤と、ヒドロシリル化触媒とを含むシリコーン組成物に関する。また、本発明は、少なくとも1つのオルガノハイドロジェンポリシロキサンの硬化生成物を含むシリコーン接着剤に関する。さらに、本発明は、シリコーン接着剤をそれぞれ含む塗装基板及び積層基板に関する。
シリコーン接着剤は、高熱安定性、良好な耐湿性、優れた柔軟性、高イオン純度、低α粒子放出、様々な基板に対する良好な接着性などの特性の独特な組合せの理由のため、様々な用途において有用である。例えば、シリコーン接着剤は、自動車産業、電子産業、建設業、家電産業(appliance industry)及び航空宇宙産業において広く使用されている。
本発明は、
(A)式(R1 2R2SiO1/2)m(R1R2SiO2/2)n(R1SiO3/2)p (I)を有する少なくとも1つのオルガノハイドロジェンポリシロキサン(式中、各R1は独立して、いずれも脂肪族不飽和を含まない、C1〜C10のヒドロカルビル又はC1〜C10のハロゲン置換ヒドロカルビルであり;各R2は独立して、R1又は−Hであり;mは0.001〜0.3であり;nは0.5〜0.999であり;pは0〜0.5であり;m+n+p=1であり;ただし、前記オルガノハイドロジェンポリシロキサンは、1分子あたり平均少なくとも2つのケイ素結合水素原子を有する)と、
(B)(i)1分子あたり平均少なくとも2つの脂肪族炭素−炭素二重結合を有する少なくとも1つの有機化合物、(ii)1分子あたり平均少なくとも2つのケイ素結合アルケニル基を有する少なくとも1つの有機シラン、(iii)1分子あたり平均少なくとも2つのケイ素結合アルケニル基を有する少なくとも1つのシリコーン樹脂、(iv)1分子あたり平均少なくとも2つのケイ素結合アルケニル基を有する少なくとも1つの有機シロキサン、並びに(v)(i)、(ii)、(iii)及び(iv)のうちの少なくとも2つを含む混合物から選択される架橋剤であって、前記オルガノハイドロジェンポリシロキサン(A)中のケイ素結合水素原子のモル数に対する前記架橋剤(B)中の脂肪族炭素−炭素二重結合のモル数の比が0.005〜0.7である架橋剤と、
(C)ヒドロシリル化触媒と
を含むシリコーン組成物に関する。
基板と、
前記基板の表面の少なくとも一部上のシリコーン接着剤塗膜であって、前記接着剤塗膜は、上記の式(I)を有する少なくとも1つのオルガノハイドロジェンポリシロキサンの硬化生成物を含むシリコーン接着剤塗膜と
を含む塗装基板に関する。
第1基板と、
前記第1基板を覆う少なくとも1つの追加基板と、
各基板の少なくとも1つの表面の少なくとも一部上のシリコーン接着剤塗膜であって、ただし、前記接着剤塗膜の少なくとも一部は、隣接する基板の反対面の間にあると共に当該反対面と直に接しており、前記接着剤塗膜は、上記の式(I)を有する少なくとも1つのオルガノハイドロジェンポリシロキサンの硬化生成物を含むシリコーン接着剤塗膜と
を含む積層基板に関する。
(A)式(R1 2R2SiO1/2)m(R1R2SiO2/2)n(R1SiO3/2)p (I)を有する少なくとも1つのオルガノハイドロジェンポリシロキサン(式中、各R1は独立して、いずれも脂肪族不飽和を含まない、C1〜C10のヒドロカルビル又はC1〜C10のハロゲン置換ヒドロカルビルであり;各R2は独立して、R1又は−Hであり;mは0.001〜0.3であり;nは0.5〜0.999であり;pは0〜0.5であり;m+n+p=1であり;ただし、前記オルガノハイドロジェンポリシロキサンは、1分子あたり平均少なくとも2つのケイ素結合水素原子を有する)と、
(B)(i)1分子あたり平均少なくとも2つの脂肪族炭素−炭素二重結合を有する少なくとも1つの有機化合物、(ii)1分子あたり平均少なくとも2つのケイ素結合アルケニル基を有する少なくとも1つの有機シラン、(iii)1分子あたり平均少なくとも2つのケイ素結合アルケニル基を有する少なくとも1つのシリコーン樹脂、(iv)1分子あたり平均少なくとも2つのケイ素結合アルケニル基を有する少なくとも1つの有機シロキサン、並びに(v)(i)、(ii)、(iii)及び(iv)のうちの少なくとも2つを含む混合物から選択される架橋剤であって、前記オルガノハイドロジェンポリシロキサン(A)中のケイ素結合水素原子のモル数に対する前記架橋剤(B)中の脂肪族炭素−炭素二重結合のモル数の比が0.005〜0.7である架橋剤と、
(C)ヒドロシリル化触媒と
を含む。
Me3SiO(MeHSiO2/2)bSiMe3、
Me3SiO(MeHSiO2/2)b(Me2SiO2/2)cSiMe3、及び
[Me3SiO(MeHSiO2/2)b]3(MeSiO3/2)
を有するポリシロキサンが挙げられるが、これらに限定されない。式中、Meはメチルであり、下付記号b及びcは、オルガノハイドロジェンポリシロキサンが500〜50,000の数平均分子量を有するような値を有する、囲まれた単位(enclosed unit)の平均数を意味する。
基板と、
前記基板の表面の少なくとも一部上のシリコーン接着剤塗膜であって、前記接着剤塗膜は、上記の式(I)を有する少なくとも1つのオルガノハイドロジェンポリシロキサンの硬化生成物を含むシリコーン接着剤塗膜と
を含む塗装基板に関する。
第1基板と、
前記第1基板を覆う少なくとも1つの追加基板と、
各基板の少なくとも1つの表面の少なくとも一部上のシリコーン接着剤塗膜であって、ただし、前記接着剤塗膜の少なくとも一部は、隣接する基板の反対面の間にあると共に当該反対面と直に接しており、前記接着剤塗膜は、上記の式(I)を有する少なくとも1つのオルガノハイドロジェンポリシロキサンの硬化生成物を含むシリコーン接着剤塗膜と
を含む。
シリコーンベースを、当該ベースの重量を基準として0.5重量%の白金触媒と混合した。得られた組成物を、メリネックス(登録商標)516PETフィルム(8インチ×11インチ(20.32cm×27.94cm))の離型剤処理された表面上に適用し、シリコーンフィルムを形成した。PETフィルムと同じ寸法を有するガラス織物を、シリコーンフィルム上に慎重に置き、当該組成物に当該織物を完全に濡らすのに十分な時間を与えた。次に、埋め込まれた織物に上記のシリコーン組成物を均一に適用した。同一のPETフィルムを、シリコーン組成物と接触する離型処理された面をもつ塗膜の上に配置した。次に、300μmの距離を離された2つのステンレス鋼バー(bar)の間に積層物を通過させた。積層物を、150℃で10分間、オーブン内で加熱した。オーブンを止め、オーブン内で積層物を室温まで冷却した。上部のPETフィルムを強化シリコーン樹脂フィルムから分離し(剥がし)、次に、シリコーン樹脂フィルムを下部のPETフィルムから分離した。透明な強化シリコーン樹脂フィルムは、約125μmの厚さを有していた。
実施例2−10のそれぞれにおいて、オルガノハイドロジェンポリシロキサン、架橋剤及び白金触媒を、表1で特定された量で混合することによって、シリコーン組成物を調製した。
比較例1−3のそれぞれにおいて、表1で特定された成分及び量を用いてシリコーン組成物を調製した。比較例1及び2では、オルガノハイドロジェンポリシロキサン、架橋剤、及び白金触媒を順々に混合した。比較例3では、オルガノハイドロジェンポリシロキサンE及び架橋剤Fを最初に混合し、次に、減圧下、100℃でキシレンを除去した。次に、この混合物を、架橋剤A及び白金触媒と混合した。
Claims (15)
- (A)式(R1 2R2SiO1/2)m(R1R2SiO2/2)n(R1SiO3/2)p (I)を有する少なくとも1つのオルガノハイドロジェンポリシロキサン(式中、各R1は独立して、いずれも脂肪族不飽和を含まない、C1〜C10のヒドロカルビル又はC1〜C10のハロゲン置換ヒドロカルビルであり;各R2は独立して、R1又は−Hであり;mは0.001〜0.3であり;nは0.5〜0.999であり;pは0〜0.5であり;m+n+p=1であり;ただし、前記オルガノハイドロジェンポリシロキサンは、1分子あたり平均少なくとも2つのケイ素結合水素原子を有する)と、
(B)(i)1分子あたり平均少なくとも2つの脂肪族炭素−炭素二重結合を有する少なくとも1つの有機化合物、(ii)1分子あたり平均少なくとも2つのケイ素結合アルケニル基を有する少なくとも1つの有機シラン、(iii)1分子あたり平均少なくとも2つのケイ素結合アルケニル基を有する少なくとも1つのシリコーン樹脂、(iv)1分子あたり平均少なくとも2つのケイ素結合アルケニル基を有する少なくとも1つの有機シロキサン、並びに(v)(i)、(ii)、(iii)及び(iv)のうちの少なくとも2つを含む混合物から選択される架橋剤であって、前記オルガノハイドロジェンポリシロキサン(A)中のケイ素結合水素原子のモル数に対する前記架橋剤(B)中の脂肪族炭素−炭素二重結合のモル数の比が0.005〜0.7である架橋剤と、
(C)ヒドロシリル化触媒と
を含むシリコーン組成物。 - 前記下付記号nは0.6〜0.9の値を有する請求項1に記載のシリコーン組成物。
- 前記下付記号pは0〜0.3の値を有する請求項1に記載のシリコーン組成物。
- 式(R1 2R2SiO1/2)m(R1R2SiO2/2)n(R1SiO3/2)p (I)を有する少なくとも1つのオルガノハイドロジェンポリシロキサン(式中、各R1は独立して、いずれも脂肪族不飽和を含まない、C1〜C10のヒドロカルビル又はC1〜C10のハロゲン置換ヒドロカルビルであり;各R2は独立して、R1又は−Hであり;mは0.001〜0.3であり;nは0.5〜0.999であり;pは0〜0.5であり;m+n+p=1であり;ただし、前記オルガノハイドロジェンポリシロキサンは、1分子あたり平均少なくとも2つのケイ素結合水素原子を有する)の硬化生成物を含むシリコーン接着剤。
- 前記下付記号nは0.6〜0.9の値を有する請求項4に記載のシリコーン接着剤。
- 前記下付記号pは0〜0.3の値を有する請求項4に記載のシリコーン接着剤。
- 基板と、
前記基板の表面の少なくとも一部上のシリコーン接着剤塗膜であって、前記接着剤塗膜は、式(R1 2R2SiO1/2)m(R1R2SiO2/2)n(R1SiO3/2)p (I)を有する少なくとも1つのオルガノハイドロジェンポリシロキサン(式中、各R1は独立して、いずれも脂肪族不飽和を含まない、C1〜C10のヒドロカルビル又はC1〜C10のハロゲン置換ヒドロカルビルであり;各R2は独立して、R1又は−Hであり;mは0.001〜0.3であり;nは0.5〜0.999であり;pは0〜0.5であり;m+n+p=1であり;ただし、前記オルガノハイドロジェンポリシロキサンは、1分子あたり平均少なくとも2つのケイ素結合水素原子を有する)の硬化生成物を含むシリコーン接着剤塗膜と
を含む塗装基板。 - 前記下付記号nは0.6〜0.9の値を有する請求項7に記載の塗装基板。
- 前記下付記号pは0〜0.3の値を有する請求項7に記載の塗装基板。
- 前記基板は、ガラス及び強化シリコーン樹脂フィルムから選択される請求項7に記載の塗装基板。
- 第1基板と、
前記第1基板を覆う少なくとも1つの追加基板と、
各基板の少なくとも1つの表面の少なくとも一部上のシリコーン接着剤塗膜であって、ただし、前記接着剤塗膜の少なくとも一部は、隣接する基板の反対面の間にあると共に当該反対面と直に接しており、前記接着剤塗膜は、式(R1 2R2SiO1/2)m(R1R2SiO2/2)n(R1SiO3/2)p (I)を有する少なくとも1つのオルガノハイドロジェンポリシロキサン(式中、各R1は独立して、いずれも脂肪族不飽和を含まない、C1〜C10のヒドロカルビル又はC1〜C10のハロゲン置換ヒドロカルビルであり;各R2は独立して、R1又は−Hであり;mは0.001〜0.3であり;nは0.5〜0.999であり;pは0〜0.5であり;m+n+p=1であり;ただし、前記オルガノハイドロジェンポリシロキサンは、1分子あたり平均少なくとも2つのケイ素結合水素原子を有する)の硬化生成物を含むシリコーン接着剤塗膜と
を含む積層基板。 - 前記下付記号nは0.6〜0.9の値を有する請求項11に記載の積層基板。
- 前記下付記号pは0〜0.3の値を有する請求項11に記載の積層基板。
- 前記基板の少なくとも1つはガラスである請求項11に記載の積層基板。
- 前記基板の少なくとも1つは強化シリコーン樹脂フィルムである請求項11に記載の積層基板。
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JP2011516626A (ja) * | 2008-03-04 | 2011-05-26 | ダウ・コーニング・コーポレイション | シリコーン組成物、シリコーン接着剤、被覆基板及び積層基板 |
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JPWO2018088316A1 (ja) * | 2016-11-11 | 2019-10-03 | ダウ・東レ株式会社 | 硬化性シリコーン組成物およびそれを用いた光半導体装置 |
Also Published As
Publication number | Publication date |
---|---|
EP2250221A1 (en) | 2010-11-17 |
KR101502312B1 (ko) | 2015-03-18 |
JP5331825B2 (ja) | 2013-10-30 |
WO2009111196A1 (en) | 2009-09-11 |
WO2009111199A1 (en) | 2009-09-11 |
KR20100137423A (ko) | 2010-12-30 |
CN101925656A (zh) | 2010-12-22 |
KR20100123855A (ko) | 2010-11-25 |
CN101959961A (zh) | 2011-01-26 |
US20110027584A1 (en) | 2011-02-03 |
EP2265674A1 (en) | 2010-12-29 |
CN101959961B (zh) | 2013-10-30 |
JP2011516626A (ja) | 2011-05-26 |
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