JP2006182688A - 紫外線吸収性基含有有機ケイ素化合物及びその製造方法並びにコーティング組成物及び被覆物品 - Google Patents
紫外線吸収性基含有有機ケイ素化合物及びその製造方法並びにコーティング組成物及び被覆物品 Download PDFInfo
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- JP2006182688A JP2006182688A JP2004377097A JP2004377097A JP2006182688A JP 2006182688 A JP2006182688 A JP 2006182688A JP 2004377097 A JP2004377097 A JP 2004377097A JP 2004377097 A JP2004377097 A JP 2004377097A JP 2006182688 A JP2006182688 A JP 2006182688A
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- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- QHUNJMXHQHHWQP-UHFFFAOYSA-N trimethylsilyl acetate Chemical compound CC(=O)O[Si](C)(C)C QHUNJMXHQHHWQP-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
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Abstract
【解決手段】 式(1)又は(2)の紫外線吸収性基含有有機ケイ素化合物。
【化1】
[R1はアルキル基又はアリール基、R2はアルキル基、R31は水素原子、ハロゲン原子、水酸基、アルキル基、アリール基又はアシロキシ基、R32〜R34は水素原子、ハロゲン原子、アルキル基、アリール基又はアルコキシ基、R35はエステル結合含有二価有機基、R36は二価炭化水素基、aは0〜2、Zは式(3)
【化2】
の基、Rは水素原子又は一価炭化水素基、R2はアルキル基、0<m≦1、0≦n≦2、0≦p<3、0≦q≦3、0<m+n+p+q<4]
【選択図】 なし
Description
で表される有機基であり、Rは同一もしくは異種の水素原子又は炭素数1〜18の非置換もしくは置換の一価炭化水素基であり、R2は同一又は異種の炭素数1〜8のアルキル基であり、m,n,p,qは、各々0<m≦1、0≦n≦2、0≦p<3、0≦q≦3、0<m+n+p+q<4を満たす数である。]
下記一般式(4)で表される(メタ)アクリル基含有ヒドロキシベンゾトリアゾールと、下記一般式(5)で表されるメルカプト基含有アルコキシシランとを、塩基の存在下で反応させることにより、前記式(1)のアルコキシシランを製造する方法。
前記式(1)のアルコキシシラン、又はこれと少なくとも1種のその他の加水分解性シラン及び/又は加水分解性シロキサンとを(共)加水分解縮合させることにより、前記式(2)のポリオルガノシロキサンを製造する方法。
前記式(1)のアルコキシシランと、少なくとも1種のその他のシラン及び/又はシロキサンとを酸あるいは塩基の存在下で平衡化反応させることにより、前記式(2)のポリオルガノシロキサンを製造する方法。
前記式(4)の(メタ)アクリル基含有ヒドロキシベンゾトリアゾールと、下記平均組成式(6)で表されるメルカプト基含有ポリオルガノシロキサンとを、塩基の存在下で反応させることにより、前記式(2)のポリオルガノシロキサンを製造する方法。
−R''−OC(=O)−R'''−
(R''は炭素数0〜17、特に1〜7の二価炭化水素基、特にアルキレン基である。R'''は炭素数2〜9の二価炭化水素基であり、特に−CH2−CH2−又は−CH(CH3)−CH2−が好ましい。)
で表される基が好ましい。
具体的には、−CH2−OC(=O)−(CH2)2−、−CH2−OC(=O)−CH(CH3)CH2−、−CH2−OC(=O)−C(CH3)2−、−(CH2)2−OC(=O)−(CH2)2−、−(CH2)2−OC(=O)−CH(CH3)CH2−、−(CH3)CH−OC(=O)−(CH2)2−、−(CH3)CH−OC(=O)−CH(CH3)CH2−、−(CH2)3−OC(=O)−(CH2)2−、−(CH2)3−OC(=O)−CH(CH3)CH2−、−(CH3)CH−OC(=O)−(CH2)2−、−(CH3)2C−OC(=O)−(CH2)2−、−(CH3)CH−OC(=O)−CH(CH3)CH2−、−(CH3)2C−OC(=O)−CH(CH3)CH2−、−(CH2)4−OC(=O)−(CH2)2−、−(CH2)4−OC(=O)−CH(CH3)CH2−、−(CH2)5−OC(=O)−(CH2)2−、−(CH2)5−OC(=O)−CH(CH3)CH2−、−(CH2)6−OC(=O)−CH(CH3)CH2−、−(CH2)8−OC(=O)−CH(CH3)CH2−、−(CH2)2−C6H10−(CH2)2−OC(=O)−CH(CH3)CH2−などを挙げることができる。入手のし易さ、経済性の観点から、−(CH2)2−OC(=O)−CH(CH3)CH2−、又は−(CH2)2−OC(=O)−CH2CH2−が好ましい。
下記一般式(4)で表される(メタ)アクリル基含有ヒドロキシベンゾトリアゾールと、下記一般式(5)で表されるメルカプト基含有アルコキシシランとを、塩基の存在下で反応させる方法。
−CH2−OC(=O)−CH=CH2、−CH2−OC(=O)−C(CH3)=CH2、−CH2CH2−OC(=O)−CH=CH2、−CH2CH2−OC(=O)−C(CH3)=CH2、−(CH2)3−OC(=O)−CH=CH2、−(CH2)3−OC(=O)−C(CH3)=CH2、−(CH2)4−OC(=O)−CH=CH2などを挙げることができる。
で表される有機基であり、Rは同一もしくは異種の水素原子又は炭素数1〜18の非置換もしくは置換の一価炭化水素基であり、R2は同一又は異種の炭素数1〜8のアルキル基であり、m,n,p,qは、各々0<m≦1、0≦n≦2、0≦p<3、0≦q≦3、0<m+n+p+q<4を満たす数である。]
本発明の前記式(1)のアルコキシシラン、又はこれと少なくとも1種のその他の加水分解性シラン及び/又は加水分解性シロキサンとを(共)加水分解縮合反応させる方法。
本発明の前記式(1)のアルコキシシランと、少なくとも1種のその他のシラン及び/又はシロキサンとを、酸あるいは塩基の存在下で平衡化反応させる方法。
前記式(4)の(メタ)アクリル基含有ヒドロキシベンゾトリアゾールと、下記平均組成式(6)で表されるメルカプト基含有ポリオルガノシロキサンとを、塩基の存在下で反応させる方法。
(R41)xSi(A)4-x
{式中R41は前記Rと同じであり、Aは同一又は異種のハロゲン原子、炭素数1〜3のアルコキシ基、炭素数1〜6のアシロキシ基、炭素数1〜6のアルケノキシ基、又はイソシアネート基である。xは0〜3の整数である。}
で表される加水分解性シラン、及びその部分加水分解縮合物が挙げられる。
(A)y(R42)3-ySi−B−Si(R43)3-z(A)z
{式中R42,R43は前記Rと同じであり、Aは前記と同じであり、Bは炭素数1以上の二価有機基であり、y、zは各々独立に0〜3の整数である。}
で表される加水分解性シラン、及びその部分加水分解縮合物も挙げることができる。
−(CH2)d−(但し、d=1〜20)、
−CH2CH2−(CF2)e−CH2CH2−(但し、e=2〜20)、
−CH2CH2−CF(CF3)−(CF2)e−CF(CF3)−CH2CH2−、
−CH2CH2−CF(C2F5)−(CF2)e−CF(C2F5)−CH2CH2−、
−CH2CH2−CF(CF3)CF2−O−(CF2)e−O−CF2CF(CF3)−CH2CH2−、
−CH2CH2−C6H4−CH2CH2−、
−CH2CH2−C6F4−CH2CH2−、
−CH2CH2−C6H10−CH2CH2−、
−CH2CH2−C6F10−CH2CH2−
(CH3O)3Si−CH2CH2−Si(OCH3)3、
(CH3O)2CH3Si−CH2CH2−SiCH3(OCH3)2、
(CH3O)3Si−CH2CH2CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−C6H4−CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−C6H10−CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−(CF2)4−CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−(CF2)6−CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−(CF2)10−CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−(CF2)16−CH2CH2−Si(OCH3)3、
(C2H5O)3Si−CH2CH2−(CF2)4−CH2CH2−Si(OC2H5)3、
(C2H5O)3Si−CH2CH2−(CF2)6−CH2CH2−Si(OC2H5)3、
(CH3O)2CH3Si−CH2CH2−(CF2)4−CH2CH2−SiCH3(OCH3)2、
(CH3O)2CH3Si−CH2CH2−(CF2)6−CH2CH2−SiCH3(OCH3)2、
(CH3O)(CH3)2Si−CH2CH2−(CF2)4−CH2CH2−Si(CH3)2(OCH3)、
(CH3O)(CH3)2Si−CH2CH2−(CF2)6−CH2CH2−Si(CH3)2(OCH3)、
(CH3O)3Si−CH2CH2−CF(CF3)(CF2)4CF(CF3)−CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−CF(CF3)(CF2)6CF(CF3)−CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−CF(CF3)(CF2)12CF(CF3)−CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−C6F10−CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−C6F4−CH2CH2−Si(OCH3)3
を挙げることができ、これらの中でも、好ましくは、
(CH3O)3Si−CH2CH2−Si(OCH3)3、
(CH3O)2CH3Si−CH2CH2−SiCH3(OCH3)2、
(CH3O)3Si−CH2CH2CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−C6H4−CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−C6H10−CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−(CF2)4−CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−(CF2)6−CH2CH2−Si(OCH3)3、
(CH3O)3Si−CH2CH2−(CF2)8−CH2CH2−Si(OCH3)3、
(C2H5O)3Si−CH2CH2−(CF2)4−CH2CH2−Si(OC2H5)3、
(C2H5O)3Si−CH2CH2−(CF2)6−CH2CH2−Si(OC2H5)3
などのシラン化合物を使用するのがよい。
で表される加水分解性シロキサン、及びその部分加水分解縮合物も挙げることができる。
(CH3O)3Si−CH2CH2−(CH3)2SiO−Si(CH3)2−CH2CH2−Si(OCH3)3、
(CH3O)3Si−O−(CH3)2SiO−Si(CH3)2−O−Si(OCH3)3、
(CH3CH2O)3Si−CH2CH2−〔(CH3)2SiO〕4−Si(CH3)2−CH2CH2−Si(OCH2CH3)3、
(CH3O)2(CH3)Si−O−〔(CH3)2SiO〕9−Si(CH3)2−O−Si(CH3)(OCH3)2、
(CH3O)3Si−CH2CH2−〔(CH3)2SiO〕20−Si(CH3)2−CH2CH2−Si(OCH3)3
また、反応時には、一般的な溶剤を使用してもよく、中でも前記に示した極性溶剤が好ましい。
また、R,R2,m,n,p,qは、上記と同様である。
これら金属酸化物微粒子の添加量は、コーティング組成物の全樹脂成分に対し、0.1〜300質量%、特に1〜100質量%であることが好ましい。
その添加量は、コーティング組成物の全樹脂成分に対し、0.1〜100質量%、特に1〜50質量%であることが好ましい。
[実施例1]
2Lのフラスコに、KBM−803(信越化学工業製;3−メルカプトプロピルトリメトキシシラン)196g(1.0モル)を仕込み、攪拌下、SM−28(川研ファインケミカル製;ナトリウムメトキシドの28%メタノール溶液)25gを滴下した。次いで、RUVA−93{大塚化学製;2−(2’−ヒドロキシ−5’−メタクリロキシエチルフェニル)−2H−ベンゾトリアゾール}323gをテトラヒドロフラン969gに予め溶解した溶液を、内温が40℃を超えないよう、冷却しながら滴下した。滴下終了後、60℃で4時間反応させた。次いで、メタンスルホン酸12.5gを投入、室温にて攪拌し、系を中和した。更に減圧濃縮後、シリカゲルを充填したカラムに通し、黄褐色透明溶液を得た。この溶液の溶剤を減圧にて除去したところ、黄褐色の粘ちょう液体を得た。この液体は、プロトン核磁気共鳴スペクトル(1H−NMR;図1)及び赤外吸収スペクトル(IR;図2)の結果から、下記式で示される化合物(純度89%)(化合物A)であった。
2Lのフラスコに、化合物A22g(0.04モル)、メチルトリメトキシシラン338g(2.24モル)、シリケート35(多摩化学工業製;テトラエトキシシランの部分加水分解縮合物、平均2量体)56g(0.16モル、0.33Siモル)、及びテトラヒドロフラン40gを仕込み、よく混合させた。次いで0.25Nの酢酸水溶液308gを滴下し、内温が40℃を超えないように冷却しながら加水分解を行った。滴下終了後、40℃以下で1時間、次いで60℃で3時間撹拌し、加水分解を完結させた。
2Lのフラスコに、一般式
(CH3O)3Si−CH2CH2−[(CH3)2SiO]d'(CH3)2Si−CH2CH2−Si(OCH3)3
{d’は平均で5である。}
30g(0.04モル)、化合物A33g(0.06モル)、及びテトラヒドロフラン38gを仕込み、よく混合させた。次いで0.05Nの硝酸水溶液50gを滴下し、内温が40℃を超えないように冷却しながら加水分解を行った。滴下終了後、40℃以下で2時間攪拌、次いで0.05Nの硝酸水溶液260gと、予め調製したメチルトリメトキシシラン330g(2.43モル)とテトラエトキシシラン104g(0.5モル)の混合物を順に投入し、40℃以下で1時間、次いで60℃で3時間撹拌し、加水分解を完結させた。
2Lのフラスコに、オクタメチルシクロテトラシロキサン716g(2.42モル)、ヘキサメチルジシロキサン36g(0.22モル)、及びメルカプトプロピルメチルジクロロシランの加水分解縮合物118g(0.88Siモル)を仕込み、よく混合させた。次いで110℃にて2時間攪拌し、脱水留去を行った。その後、室温まで冷却し、活性白土(和光純薬工業製)48gを投入し、80℃にて7時間攪拌し、重合を行った。室温まで冷却後、濾過により活性白土を取り除き、無色透明のメルカプト基含有ポリオルガノシロキサン(メルカプト当量980)を得た。
2Lのフラスコに、化合物A52g(0.10モル)、メチルトリエトキシシラン100g(0.56モル)、γ−グリシドキシプロピルトリメトキシシラン99g(0.42モル)、及び(CH3O)3SiCH2CH2−C4F8−CH2CH2Si(OCH3)3100g(0.20モル)を仕込み、よく混合した。次いで0.25N酢酸水溶液508gを滴下し、内温が40℃を超えないように冷却しながら加水分解を行った。滴下終了後、40℃以下で12時間攪拌し、メタノールシリカゾル(日産化学工業製;メタノール分散品、固形分30%)600gを投入し、室温で1時間攪拌した。その後、不揮発分濃度が20%になるようイソブタノールで希釈、濾紙濾過を行い、淡黄色殆ど透明のポリオルガノシロキサンEの溶液を得た。
実施例2において、化合物Aを使用しないこと以外は、同様にして紫外線吸収性を有さないポリオルガノシロキサンFの溶液を得た。
実施例5において、化合物Aを使用しないこと以外は、同様にして紫外線吸収性を有さないポリオルガノシロキサンGの溶液を得た。
[実施例6]
実施例2で得られたポリオルガノシロキサンBの溶液に、各種添加剤を表1に示した量で配合し、よく混合後、濾紙濾過を行い、コーティング組成物1を得た。これを石英ガラス板(厚さ1mm×長さ4cm×幅1cm)に流し塗り法により塗布し、130℃で1時間硬化させた。得られた塗膜に関して、透過スペクトルを測定したところ、図3に示したとおり、波長390nm以下の領域の紫外線を吸収していることが判明した。
実施例6において、ポリオルガノシロキサンBの溶液の代わりに、比較例1で得られたポリオルガノシロキサンFの溶液を用いて、同様にコーティング組成物2を得た。更に実施例6と同様、塗膜を得、その透過スペクトルを測定したところ、図4に示したとおり、紫外線をほとんど吸収しないことが判明した。
実施例2、3及び5、比較例2で得られたポリオルガノシロキサン溶液と、各種添加剤とを表1に示す量で配合し、コーティング組成物3〜8とした。これらコーティング組成物をポリカーボネート/アクリル樹脂共押し出し板(厚さ0.5mm×長さ30cm×幅20cm)のアクリル樹脂面に流し塗り法により塗布し、130℃で1時間硬化させた。
TBAH:テトラブチルアンモニウムヒドロキシドの0.25%水溶液
酢酸Na:酢酸ナトリウムの10%水溶液
AlAA:アルミニウムアセチルアセトナート
LV−I:フロラードFC−4430(住友スリーエム製)の10%イソプロパノール溶液
UVA−I:2−[4−[(2−ヒドロキシ−3−ドデシル/トリデシル−オキシプロピル)オキシ]−2−ヒドロキシフェニル]−4,6−ビス(2,4−ジメチルフェニル)−1,3,5−トリアジン(チヌビン400、チバ・スペシャリティ・ケミカルズ製)
UVA−II:2−(2’−ヒドロキシ−5’−メタクリロキシエチルフェニル)−2H−ベンゾトリアゾール(RUVA−93、大塚化学製)
UVA−III:2,4−ジヒドロキシベンゾフェノン(SEESORB 100、シプロ化成製)
HALS−I:N−アセチル−3−ドデシル−1−(2,2,6,6−テトラメチル−4−ピペリジニル)ピロリジン−2,5−ジオン(サンドバー3058Liq.、クラリアント・ジャパン製)
微粒子−I:酸化チタン含有複合金属酸化物ゾルの20%メタノール分散品(オプトレイク1120Z、触媒化成工業製)
<塗膜外観>
塗膜を目視で観察し、異常の有無を判定した。
ASTM1044に準じ、テーバー摩耗試験機にて摩耗輪CS−10Fを装着、荷重500g下での500回転後の曇価を測定し、試験後と試験前の曇価差を耐擦傷性とした。
JIS K5400に準じ、カミソリ刃を用いて、塗膜に2mm間隔で縦、横6本ずつ切れ目を入れて25個の碁盤目を作製し、セロテープ(ニチバン社製)をよく付着させた後、90°手前方向に急激に剥がした時、塗膜が剥離せずに残存したマス目数(X)を、X/25で表示した。
評価サンプルを、沸騰水に2時間浸漬した後の外観変化及び密着性を評価した。
評価サンプルを、130℃の熱風循環乾燥機中で1時間加熱した後のクラックの有無を目視で観察した。
アクリル系プライマーであるプライマーPC−7A(信越化学工業製)を、ポリカーボネート樹脂板(厚さ0.5mm×長さ30cm×幅20cm)に、流し塗り法により塗布、130℃で30分硬化した後、室温下、1時間冷却した。その後、前記組成物の被膜上に実施例6〜9及び比較例3,4,6で調製したコーティング組成物1〜6及び8を各々流し塗り法により塗布し、130℃で1時間硬化させた。得られた塗膜に関して、下記の耐候性評価を行った結果を表3に示す。本発明の紫外線吸収性基含有有機ケイ素化合物を含むコーティング組成物からなる塗膜は、基材であるポリカーボネート樹脂が劣化する紫外線波長領域を効果的に吸収しているため、耐候性試験後の黄変度は初期値と同等もしくはわずかな上昇のみであり、塗膜異常も認められなかった。一方、本発明の紫外線吸収性基含有有機ケイ素化合物を含まないコーティング組成物の塗膜では耐候性試験後の黄変度は上昇し、塗膜異常も発生した。
アクリル系プライマーであるプライマーPC−7A(信越化学工業製)に、実施例1の化合物Aを、PC−7Aの固形分量に対して固形分として8%配合した組成物、ポリカーボネート樹脂板(厚さ0.5mm×長さ30cm×幅20cm)に、流し塗り法により塗布、130℃で30分硬化した後、室温下、1時間冷却した。その後、前記組成物の被膜上に実施例6で調製したコーティング組成物1を流し塗り法により塗布し、130℃で1時間硬化させた。得られた塗膜に関して、下記の耐候性評価を行った結果を表3に示す。
岩崎電気(株)製アイスーパーUVテスターW−151を使用し、[ブラックパネル温度63℃、湿度50%RH、照度50mW/cm2、降雨10秒/1時間で5時間]→[ブラックパネル温度30℃、湿度95%RHで1時間]を1サイクルとして、このサイクルを繰り返す条件で100時間、250時間の試験を行った。耐候性試験前後に、JIS K7103に準拠し、黄変度を、また耐候塗膜クラック、耐候塗膜剥離の状態を目視又は顕微鏡(倍率250倍)にて観察した。
耐候性試験後の塗膜外観を下記の基準で評価した。
○:異常なし
△:僅かにクラックあり
×:塗膜全体にクラックあり
耐候性試験後の塗膜の状態を下記の基準で評価した。
○:異常なし
△:コーティング組成物の硬化塗膜層とプライマー硬化塗膜層との間で一部剥離
×:コーティング組成物の硬化塗膜層とプライマー硬化塗膜層との間で全剥離
Claims (11)
- 下記一般式(1)で表される紫外線吸収性基含有有機ケイ素化合物。
- R1がメチル基、R2がメチル基又はエチル基、R31が水素原子、R32,R33,R34が各々水素原子、R35が下記式(7)又は(8)で表される二価有機基、R36が−CH2CH2CH2−、aが0又は1であることを特徴とする請求項1記載の有機ケイ素化合物。
- 下記平均組成式(2)で表される紫外線吸収性基含有有機ケイ素化合物。
で表される有機基であり、Rは同一もしくは異種の水素原子又は炭素数1〜18の非置換もしくは置換の一価炭化水素基であり、R2は同一又は異種の炭素数1〜8のアルキル基であり、m,n,p,qは、各々0<m≦1、0≦n≦2、0≦p<3、0≦q≦3、0<m+n+p+q<4を満たす数である。] - Rがメチル基、エチル基、トリフロロプロピル基、フェニル基、ビニル基、γ−アクリロキシプロピル基、γ−メタクリロキシプロピル基、γ−グリシドキシプロピル基、3,4−エポキシシクロヘキシルエチル基、γ−メルカプトプロピル基又はγ−アミノプロピル基、R2がメチル基、エチル基又はプロピル基、R31が水素原子、R32,R33,R34が各々水素原子、R35が下記式(7)又は(8)で表される二価有機基、R36が−CH2CH2CH2−、m,n,p,qが、0.001≦m≦1、0.01≦n≦1.99、0≦p<2.99、0≦q≦2.99、0.001≦m+n+p+q<3を満たす数であることを特徴とする請求項3記載の有機ケイ素化合物。
- 下記一般式(4)で表される(メタ)アクリル基含有ヒドロキシベンゾトリアゾールと、下記一般式(5)で表されるメルカプト基含有アルコキシシランとを、塩基の存在下で反応させることを特徴とする請求項1記載の有機ケイ素化合物の製造方法。
- 請求項1記載の有機ケイ素化合物、又はこれと少なくとも1種のその他の加水分解性シラン及び/又は加水分解性シロキサンとを(共)加水分解縮合反応させることを特徴とする請求項3記載の有機ケイ素化合物の製造方法。
- 請求項1記載の有機ケイ素化合物と、少なくとも1種のその他のシラン及び/又はシロキサンとを酸あるいは塩基の存在下で平衡化反応させることを特徴とする請求項3記載の有機ケイ素化合物の製造方法。
- 下記一般式(4)で表される(メタ)アクリル基含有ヒドロキシベンゾトリアゾールと、下記平均組成式(6)で表されるメルカプト基含有ポリオルガノシロキサンとを、塩基の存在下で反応させることを特徴とする請求項3記載の有機ケイ素化合物の製造方法。
- 請求項1乃至4のいずれか1項記載の有機ケイ素化合物を含有するコーティング組成物。
- 基材に直接又は少なくとも1種の他の層を介して請求項9記載のコーティング組成物の硬化被膜を被覆してなる被覆物品。
- 基材が、ガラス、金属、セラミックス、有機樹脂、木材又は繊維である請求項10記載の被覆物品。
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