JPH05320517A - Moisture-curable and radically polymerizable and curable silicone composition - Google Patents
Moisture-curable and radically polymerizable and curable silicone compositionInfo
- Publication number
- JPH05320517A JPH05320517A JP4165225A JP16522592A JPH05320517A JP H05320517 A JPH05320517 A JP H05320517A JP 4165225 A JP4165225 A JP 4165225A JP 16522592 A JP16522592 A JP 16522592A JP H05320517 A JPH05320517 A JP H05320517A
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- moisture
- radical polymerization
- curable
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はラジカル重合硬化及び湿
気硬化の両硬化機能によって硬化しうるオルガノポリシ
ロキサン組成物に関する。FIELD OF THE INVENTION This invention relates to organopolysiloxane compositions that are curable by both radical polymerization and moisture curing functions.
【０００２】[0002]
【従来技術とその課題】シリコーンは、柔軟な硬化物と
その弾性に富んだ性能を活かし耐衝撃性、耐振動性、耐
熱応力性など産業的利用価値の高い物質である。しか
し、従来の一液のシリコーンは湿気により縮合反応して
硬化するため、完全硬化するのにかなりの時間を要す
る。そのため、近年では光照射にて硬化するシリコーン
が開発されている。例えば、末端シラノールオルガノポ
リシロキサンをアミノアルコキシシランで処理し末端を
アミノ基に変えてグリシジル（メタ）アクリレートを付
加させ光硬化を可能にしたものがある（特開昭５５−１
１２２６２）。しかし、このグリシジル基とアミノ基の
反応性は悪く、反応に際し高温にて長時間加熱反応した
り、触媒を使用したりしなければならない。また、グリ
シジル（メタ）アクリレートの付加反応に関しては、エ
ポキシ基とアクリル基の反応性が似ているために、アク
リル基が反応し光硬化が付与されないこともある。2. Description of the Related Art Silicone is a substance having a high industrial value such as impact resistance, vibration resistance, and thermal stress resistance by utilizing a flexible cured product and its elasticity-rich performance. However, since the conventional one-component silicone cures by condensation reaction due to moisture, it takes a considerable time to completely cure. Therefore, in recent years, silicones that are cured by light irradiation have been developed. For example, there is one in which a terminal silanol organopolysiloxane is treated with an aminoalkoxysilane to change the terminal to an amino group and a glycidyl (meth) acrylate is added to enable photocuring (Japanese Patent Laid-Open No. 55-1).
12262). However, the reactivity between the glycidyl group and the amino group is poor, and during the reaction, it is necessary to carry out a heating reaction at a high temperature for a long time or to use a catalyst. Further, regarding the addition reaction of glycidyl (meth) acrylate, since the reactivity of the epoxy group is similar to that of the acrylic group, the acrylic group may react and the photocuring may not be imparted.
【０００３】本発明の目的はかかる従来技術の欠点を解
決することにあり、特に優れたラジカル重合硬化性と湿
気硬化性を持ち製造が容易なシリコーン組成物を提供す
ることにある。An object of the present invention is to solve the above drawbacks of the prior art, and to provide a silicone composition which has particularly excellent radical polymerization curability and moisture curability and is easy to manufacture.
【０００４】[0004]
【課題を解決する手段】本発明は分子両末端にアミノ基
を有するポリオルガノシロキサンと（メタ）アクリル酸
誘導体との縮合反応生成物とラジカル重合開始剤及び湿
気硬化触媒からなることを特徴とする湿気硬化及びラジ
カル重合硬化しうるシリコーン組成物に関する。The present invention is characterized by comprising a condensation reaction product of a polyorganosiloxane having amino groups at both ends of a molecule and a (meth) acrylic acid derivative, a radical polymerization initiator and a moisture curing catalyst. It relates to a moisture-curable and radical-polymerizable silicone composition.
【０００５】本発明者は、末端シラノールポリオルガノ
シロキサンにアミノ基を付加して、（メタ）アクリル酸
無水物や（メタ）アクリル酸や（メタ）アクリル酸クロ
ライドなどを反応させることによりラジカル重合硬化性
付与が阻害されることを防ぎ、さらに縮合反応を短時間
で行なうことができることを知見し、本発明に到達し
た。The present inventor has conducted radical polymerization curing by adding an amino group to a terminal silanol polyorganosiloxane and reacting it with (meth) acrylic anhydride, (meth) acrylic acid, (meth) acrylic acid chloride or the like. The present invention has been accomplished by finding that it is possible to prevent the impartation of a property from being inhibited and to carry out the condensation reaction in a short time.
【０００６】次に本発明のシリコーン組成物を構成する
成分について説明する。Next, the components constituting the silicone composition of the present invention will be described.
【０００７】本発明は湿気硬化及びラジカル重合硬化の
両硬化機構によって硬化しうる組成物であって前記組成
物が （イ）一般式The present invention is a composition which can be cured by both curing mechanism of moisture curing and radical polymerization curing, wherein the composition is
【化２】 （式中Ｒ１及びＲ３は二価の炭化水素基、Ｒ２及びＲ４
は一価の炭化水素基、Ｘは水酸基または加水分解可能な
基を表し、ｋは０〜４の整数、ｍは５０〜１００００の
整数、ａは０、１である）で示されるオルガノポリシロ
キサンと（ロ）１分子中にラジカル重合官能基であるビ
ニル基を少なくとも１個もち、且つアミノ基と反応可能
な基をもつ化合物との縮合反応物、および（ハ）ラジカ
ル重合開始剤及び湿気硬化触媒からなることを特徴とす
るラジカル重合硬化性及び湿気硬化性オルガノポリシロ
キサン組成物にある。[Chemical 2] (In the formula, R 1 and R 3 are divalent hydrocarbon groups, R 2 and R 4
Represents a monovalent hydrocarbon group, X represents a hydroxyl group or a hydrolyzable group, k is an integer of 0 to 4, m is an integer of 50 to 10000, and a is 0 or 1). And (b) a condensation reaction product of a compound having at least one vinyl group which is a radical polymerization functional group in one molecule and having a group capable of reacting with an amino group, and (c) a radical polymerization initiator and moisture curing. A radical polymerization curable and moisture curable organopolysiloxane composition comprising a catalyst.
【０００８】イ）分子両末端にアミノ基を有するポリオ
ルガノシロキサンの典型例は一般式A) A typical example of the polyorganosiloxane having amino groups at both ends of the molecule is represented by the general formula
【化３】 （式中Ｒ１及びＲ３は二価の炭化水素基、Ｒ２及びＲ４
は一価の炭化水素基、Ｘは水酸基または加水分解可能な
基を表し、ｋは０〜４の整数、ｍは５０〜１００００の
整数、ａは０、１である）で示されるオルガノポリシロ
キサンであり、式中のＲ１及びＲ３で示される二価の炭
化水素基としてはメチレン基、エチレン基、プロピレン
基、などのアルキレン基、フェニレン基などのアリーレ
ン基などが例示され、また、Ｒ２及びＲ４で示される一
価の炭化水素基としてはメチル基、エチル基、プロピル
基、ブチル基などのアルキル基、ビニル基、アリル基な
どのアルケニル基、フェニル基などのアリール基、ある
いはこれらの基の水素原子が部分的にハロゲン原子など
で置換された基などが例示される。また、Ｘで示される
加水分解可能な基としてはメトキシ基、エトキシ基、プ
ロポキシ基などのアルコキシ基やオキシム基、アミノ
基、プロペノキシ基、アセトキシ基などが例示される。[Chemical 3] (In the formula, R 1 and R 3 are divalent hydrocarbon groups, R 2 and R 4
Represents a monovalent hydrocarbon group, X represents a hydroxyl group or a hydrolyzable group, k is an integer of 0 to 4, m is an integer of 50 to 10000, and a is 0 or 1). Examples of the divalent hydrocarbon group represented by R 1 and R 3 in the formula include an alkylene group such as a methylene group, an ethylene group and a propylene group, an arylene group such as a phenylene group, and the like. Examples of the monovalent hydrocarbon group represented by 2 and R 4 include an alkyl group such as a methyl group, an ethyl group, a propyl group and a butyl group, an alkenyl group such as a vinyl group and an allyl group, an aryl group such as a phenyl group, or the like. Examples thereof include a group in which a hydrogen atom of the group is partially substituted with a halogen atom or the like. Examples of the hydrolyzable group represented by X include an alkoxy group such as a methoxy group, an ethoxy group and a propoxy group, an oxime group, an amino group, a propenoxy group and an acetoxy group.
【０００９】このようなオルガノポリシロキサンは従来
から知られている方法、例えば式Such organopolysiloxanes can be prepared by methods known in the art, such as those of the formula
【化４】 （式中、Ｒは上記したＲ２と同じ意味であり、ｎは正の
整数を表す）で示される分子鎖両末端が水酸基で封鎖さ
れたジオルガノポリシロキサンと１分子中に加水分解基
を２個または３個もち、他の反応基としてアミノ基をも
つ反応性シラン化合物とを反応させることにより合成す
ることができる。[Chemical 4] (In the formula, R has the same meaning as R 2 described above and n represents a positive integer.) A diorganopolysiloxane having both ends of the molecular chain blocked with hydroxyl groups and a hydrolyzable group in one molecule. It can be synthesized by reacting with a reactive silane compound having two or three and having an amino group as another reactive group.
【００１０】上記の反応に用いられる反応性シラン化合
物としては、（β−アミノエチル）−β−アミノエチル
トリアルコキシシラン、（β−アミノエチル）−γ−ア
ミノプロピルトリアルコキシシラン、（γ−アミノプロ
ピル）−β−アミノエチルトリアルコキシシラン、（γ
−アミノプロピル）−γ−アミノプロピルトリアルコキ
シシラン、アミノプロピルトリアルコキシシラン、アミ
ノプロピルメチルジアルコキシシランや下記のアミノシ
ラン化合物などが例示される。The reactive silane compound used in the above reaction includes (β-aminoethyl) -β-aminoethyltrialkoxysilane, (β-aminoethyl) -γ-aminopropyltrialkoxysilane and (γ-amino). Propyl) -β-aminoethyltrialkoxysilane, (γ
Examples include -aminopropyl) -γ-aminopropyltrialkoxysilane, aminopropyltrialkoxysilane, aminopropylmethyldialkoxysilane, and the following aminosilane compounds.
【化５】 [Chemical 5]
【００１１】ロ）１分子中にラジカル重合官能基である
ビニル基を少なくとも１個もち、且つアミノ基と反応可
能な基をもつ化合物としては、具体例として（メタ）ア
クリル酸無水物や（メタ）アクリル酸や（メタ）アクリ
ル酸クロライドなどの（メタ）アクリル酸誘導体があ
る。(B) Specific examples of the compound having at least one vinyl group which is a radical polymerization functional group in one molecule and having a group capable of reacting with an amino group include (meth) acrylic anhydride and (meth) ) There are (meth) acrylic acid derivatives such as acrylic acid and (meth) acrylic acid chloride.
【００１２】縮合反応は通常アミノ基含有オルガノポリ
シロキサンのアミノ基に（メタ）アクリル酸誘導体が十
分反応する量関係で両者を混合することによって行われ
る。通常前者を１モルに対し後者を２モル以上添加し、
室温〜５０℃前後といった温度で縮合反応させる。ま
た、反応を進行させるために縮合物と反応する化合物を
加えることもできる。The condensation reaction is usually carried out by mixing both of the amino group-containing organopolysiloxanes in such a quantity that the (meth) acrylic acid derivative reacts sufficiently with the amino groups. Usually, the former is added in an amount of 2 mol or more with respect to 1 mol,
The condensation reaction is carried out at a temperature such as room temperature to around 50 ° C. In addition, a compound that reacts with the condensate can be added to promote the reaction.
【００１３】イ）及びロ）成分は通常予め縮合反応さ
れ、その生成物が後記するハ）成分と組合せられる。The components a) and b) are usually subjected to a condensation reaction in advance, and the product thereof is combined with the component c) described below.
【００１４】ハ）ラジカル重合開始剤としては、光開始
剤、熱重合開始剤、レドックス重合開始剤などがある。(C) Examples of radical polymerization initiators include photoinitiators, thermal polymerization initiators, redox polymerization initiators, and the like.
【００１５】ラジカル重合開始剤として光開始剤を例示
すると次のようなものがある。ジメトキシアセトフェノ
ン、ジエトキシフェニルケトン、１−ヒドロキシヘキシ
ルフェニルケトン、アセトフェノン、プロピオフェノ
ン、ベンゾフェノン、キサントール、フルオレイン、ベ
ンズアルデヒド、アンスラキノン、トリフェニルアミ
ン、カルバゾール、３−メチルアセトフェノン、４−メ
チルアセトフェノン、３−ペンチルアセトフェノン、４
−メトキシアセトフェノン、３−ブロモアセトフェノ
ン、ｐ−ジアセチルベンゼン、３−メトキシベンゾフェ
ノン、４−アリルアセトフェノン、４−メチルベンゾフ
ェノン、４−クロロ−４−ベンジルベンゾフェノン、３
−クロロキサントーン、３，９−ジクロロキサントー
ン、３−クロロ−８−ノニルキサントーン、ベンゾイ
ル、ベンゾインメチルエーテル、ベンゾインブチルエー
テル、ビス（４−ジメチルアミノフェニル）ケトン、ベ
ンジルメトキシケタール、２−クロロチオキサトーンな
どがあげられる。なお光重合触媒の添加量は系を僅かに
光感応化するだけでよいので、この組成物に存在するオ
リゴマーの総重量を基準にして０．０１〜１０重量％で
よいが、一般には０．１〜５重量％が好ましい。Examples of photoinitiators as radical polymerization initiators include the following. Dimethoxyacetophenone, diethoxyphenyl ketone, 1-hydroxyhexylphenyl ketone, acetophenone, propiophenone, benzophenone, xanthol, fluorein, benzaldehyde, anthraquinone, triphenylamine, carbazole, 3-methylacetophenone, 4-methylacetophenone, 3 -Pentyl acetophenone, 4
-Methoxyacetophenone, 3-bromoacetophenone, p-diacetylbenzene, 3-methoxybenzophenone, 4-allylacetophenone, 4-methylbenzophenone, 4-chloro-4-benzylbenzophenone, 3
-Chloroxanthone, 3,9-dichloroxanthone, 3-chloro-8-nonylxanthone, benzoyl, benzoin methyl ether, benzoin butyl ether, bis (4-dimethylaminophenyl) ketone, benzyl methoxy ketal, 2-chlorothione Oxatone etc. can be mentioned. The amount of the photopolymerization catalyst to be added may be 0.01 to 10% by weight based on the total weight of the oligomers present in the composition, since it is sufficient to slightly sensitize the system. 1-5% by weight is preferred.
【００１６】また、ラジカル重合開始剤として光開始剤
だけでなく、熱重合開始剤やレゾックス重合開始剤など
も併用して、熱重合性、レゾックス重合性などを付与す
ることもできる。As the radical polymerization initiator, not only a photoinitiator but also a thermal polymerization initiator, a resox polymerization initiator and the like may be used in combination to impart thermal polymerization property and resox polymerization property.
【００１７】湿気硬化触媒としては、鉛−２−エチルオ
クトエート、ジブチルすずジアセテート、ジブチルすず
ジラウレート、ブチルすずトリ−２−エチルヘキソエー
ト、鉄−２−エチルヘキソエート、コバルト−２−エチ
ルヘキソエート、マンガン−２−エチルヘキソエート、
亜鉛−２−エチルヘキソエート、カプリル酸第１すず、
ナフテン酸すず、オレイン酸すず、ブチル酸すず、ナフ
テン酸すず、ナフテン酸亜鉛、ナフテン酸コバルト、ス
テアリン酸亜鉛などの有機酸カルボン酸の金属鉛；テト
ラブチルチタネート、テトラ−２−エチルヘキシルチタ
ネート、トリエタノールアミンチタネート、テトラ（イ
ソプロペニルオキシ）チタネートなどの有機チタン酸エ
ステル；オルガノシロキシチタン、β−カルボニルチタ
ンなどの有機チタン化合物；アルコキシアルミニウム化
合物；ベンジルトリエチルアンモニウムアセテートなど
の第４級アンモニウム塩；酢酸カリウム、酢酸ナトリウ
ム、しゅう酸リチウムなどのアルカリ金属の低級脂肪
酸；ジメチルヒドロキシアミン、ジエチルヒドロキシア
ミンなどのジアルキルヒドロキシルアミン；などがあげ
られる。この湿気硬化触媒の使用量は、オリゴマー総重
量に対して０．０１〜１０重量部、特に０．１〜５重量
部が好ましい。Moisture curing catalysts include lead-2-ethyloctoate, dibutyltin diacetate, dibutyltin dilaurate, butyltin tri-2-ethylhexoate, iron-2-ethylhexoate, cobalt-2- Ethylhexoate, manganese-2-ethylhexoate,
Zinc-2-ethylhexoate, first tin caprylic acid,
Metallic lead of organic acid carboxylic acid such as tin naphthenate, tin oleate, tin butyrate, tin naphthenate, zinc naphthenate, cobalt naphthenate, zinc stearate; tetrabutyl titanate, tetra-2-ethylhexyl titanate, triethanol Organic titanate esters such as amine titanate and tetra (isopropenyloxy) titanate; organotitanium compounds such as organosiloxytitanium and β-carbonyltitanium; alkoxyaluminum compounds; quaternary ammonium salts such as benzyltriethylammonium acetate; potassium acetate; Examples thereof include lower fatty acids of alkali metals such as sodium acetate and lithium oxalate; dialkylhydroxylamine such as dimethylhydroxyamine and diethylhydroxyamine. The amount of the moisture curing catalyst used is preferably 0.01 to 10 parts by weight, particularly 0.1 to 5 parts by weight, based on the total weight of the oligomer.
【００１８】本発明の組成物は基本的には上記成分から
なるが、必要に応じて各種添加剤を併用しうる。特にヒ
ュームドシリカの併用は硬化物の物性向上の上で好まし
い。The composition of the present invention basically comprises the above-mentioned components, but various additives may be used in combination if necessary. In particular, the combined use of fumed silica is preferable from the viewpoint of improving the physical properties of the cured product.
【００１９】また、粘度調整のために、ジメチルシリコ
ーンオイルや反応性希釈剤などを添加しても良い。例え
ば、反応性希釈剤としては、不飽和二重結合基を有する
化合物や加水分解可能な基を有する化合物等がある。Further, dimethyl silicone oil, a reactive diluent or the like may be added to adjust the viscosity. For example, the reactive diluent includes a compound having an unsaturated double bond group, a compound having a hydrolyzable group, and the like.
【００２０】[0020]
【実施例】製造例１ 末端シラノールポリジメチルシロキサン（分子量３００
００）１０００ｇにアミノプロピルトリメトキシシラン
１２ｇを加えて、窒素置換中にて１００℃２時間攪拌反
応する。その後真空に引き過剰なアミノプロピルトリメ
トキシシランを取り除き、粘度１５０００ｃｐｓ末端ア
ミノポリジメチルシロキサンが得られた。EXAMPLES Production Example 1 Terminal silanol polydimethylsiloxane (molecular weight 300
(00) 12g of aminopropyltrimethoxysilane is added to 1000g, and the mixture is reacted with stirring at 100 ° C for 2 hours while purging with nitrogen. Then, vacuum was drawn to remove excess aminopropyltrimethoxysilane, and a viscosity of 15000 cps terminal aminopolydimethylsiloxane was obtained.
【００２１】製造例２ 末端シラノールポリジメチルシロキサン（分子量３００
００）１０００ｇにアミノエチルアミノプロピルトリメ
トキシシラン１５ｇを加えて、窒素置換中にて１００℃
２時間攪拌反応する。その後真空に引き過剰なアミノエ
チルアミノプロピルトリメトキシシランを取り除き、粘
度１８０００ｃｐｓ末端アミノポリジメチルシリコーン
が得られた。Production Example 2 Terminal silanol polydimethylsiloxane (molecular weight 300
00) 1000 g, and 15 g of aminoethylaminopropyltrimethoxysilane were added, and the temperature was 100 ° C. under nitrogen substitution.
React with stirring for 2 hours. Then, vacuum was drawn to remove excess aminoethylaminopropyltrimethoxysilane, and a viscosity of 18000 cps terminated aminopolydimethylsilicone was obtained.
【００２２】実施例１ 製造例１で得られた樹脂１００ｇにメタクリル酸無水物
１．０ｇを加え窒素置換中にて５０℃１時間攪拌反応す
る。さらに、ラジカル重合硬化触媒として１−ヒドロキ
シシクロヘキシルフェニルケトン１ｇと湿気硬化触媒と
してジブチルスズジラウレート０．５ｇを加え湿気およ
び紫外線硬化性シリコーン組成物を得た。Example 1 To 100 g of the resin obtained in Production Example 1 was added 1.0 g of methacrylic acid anhydride, and the mixture was reacted with stirring at 50 ° C. for 1 hour under nitrogen substitution. Further, 1 g of 1-hydroxycyclohexyl phenyl ketone as a radical polymerization curing catalyst and 0.5 g of dibutyltin dilaurate as a moisture curing catalyst were added to obtain a moisture- and UV-curable silicone composition.
【００２３】実施例２ 製造例１で得られた樹脂１００ｇにメタクリロイルクロ
ライド０．７ｇとトリエチルアミン０．７ｇを加え窒素
置換中にて室温１時間攪拌反応する。さらに、１００ｃ
ｐｓのジメチルシリコーンオイル４０ｇとラジカル重合
硬化触媒としてジメトキシアセトフェノン１ｇおよび湿
気硬化触媒ジブチルスズジラウレート０．５ｇを加え湿
気および紫外線硬化性シリコーン組成物が得られた。Example 2 To 100 g of the resin obtained in Production Example 1 was added 0.7 g of methacryloyl chloride and 0.7 g of triethylamine, and the mixture was stirred for 1 hour at room temperature under nitrogen substitution. Furthermore, 100c
40 g of ps dimethyl silicone oil, 1 g of dimethoxyacetophenone as a radical polymerization curing catalyst and 0.5 g of a moisture curing catalyst dibutyltin dilaurate were added to obtain a moisture and ultraviolet curable silicone composition.
【００２４】実施例３ 製造例２で得られた樹脂１００ｇにメタクリル酸無水物
１ｇを加え窒素置換中にて室温１時間攪拌反応する。さ
らに、ラジカル重合硬化触媒として１−ヒドロキシシク
ロヘキシルフェニルケトン１ｇと湿気硬化触媒としてオ
クチル酸錫０．５ｇを加え湿気および紫外線硬化性シリ
コーン組成物が得られた。Example 3 To 100 g of the resin obtained in Production Example 2 was added 1 g of methacrylic acid anhydride, and the mixture was reacted with stirring at room temperature for 1 hour under nitrogen substitution. Further, 1 g of 1-hydroxycyclohexyl phenyl ketone as a radical polymerization curing catalyst and 0.5 g of tin octylate as a moisture curing catalyst were added to obtain a moisture- and UV-curable silicone composition.
【００２５】実施例４ 製造例２で得られた樹脂１００ｇにアクリル酸０．５ｇ
とジシクロヘキシルカルボジイミド１．４ｇを加え窒素
置換中にて５０℃１時間攪拌反応する。さらに、１００
ｃｐｓのジメチルシリコーンオイル４０ｇとラジカル重
合硬化触媒としてジメトキシアセトフェノン１ｇおよび
湿気硬化触媒としてオクチル酸錫０．５ｇを加え湿気お
よび紫外線硬化性シリコーン組成物を得た。Example 4 0.5 g of acrylic acid was added to 100 g of the resin obtained in Production Example 2.
And 1.4 g of dicyclohexylcarbodiimide are added, and the mixture is stirred and reacted under nitrogen substitution at 50 ° C. for 1 hour. In addition, 100
40 g of dimethyl silicone oil of cps, 1 g of dimethoxyacetophenone as a radical polymerization curing catalyst and 0.5 g of tin octylate as a moisture curing catalyst were added to obtain a moisture and ultraviolet ray curable silicone composition.
【００２６】これら実施例で得られた樹脂組成物を深さ
５ｍｍ×１５０ｍｍ×１５０ｍｍの容量に満たし、４ｋ
Ｗ高圧水銀灯で１５０ｍＷ／ｃｍ２×２０秒照射したと
ころ硬化がおこった。得られた硬化物の硬度（ＪＩＳ硬
度Ａタイプ）と引っ張り強度、伸び率を測定した。ま
た、紫外線未照射の湿気硬化物は温度２５℃、湿度６０
％の雰囲気下に放置したところ２４時間後には表面が硬
化しタックが全くない状態となった。７日後の硬度（Ｊ
ＩＳ硬度Ａタイプ）、引っ張り強度、伸び率を測定し
た。結果を表１に示す。The resin compositions obtained in these examples were filled in a volume of 5 mm × 150 mm × 150 mm in depth and 4 k
Curing occurred when irradiated with a W high pressure mercury lamp for 150 mW / cm 2 × 20 seconds. The hardness (JIS hardness A type), tensile strength, and elongation of the obtained cured product were measured. In addition, moisture-cured products that have not been irradiated with ultraviolet rays have a temperature of 25 ° C and a humidity of 60.
%, The surface was hardened after 24 hours, and there was no tack at all. Hardness after 7 days (J
IS hardness A type), tensile strength, and elongation were measured. The results are shown in Table 1.
【００２７】[0027]
【表１】 [Table 1]
Claims (2)
機構によって硬化しうる組成物であって前記組成物が （イ）一般式 【化１】 （式中Ｒ１及びＲ３は二価の炭化水素基、Ｒ２及びＲ４
は一価の炭化水素基、Ｘは水酸基または加水分解可能な
基を表し、ｋは０〜４の整数、ｍは５０〜１００００の
整数、ａは０、１である）で示されるオルガノポリシロ
キサンと（ロ）１分子中にラジカル重合官能基であるビ
ニル基を少なくとも１個もち、且つアミノ基と反応可能
な基をもつ化合物との縮合反応物、および（ハ）ラジカ
ル重合開始剤及び湿気硬化触媒からなることを特徴とす
るラジカル重合硬化性及び湿気硬化性オルガノポリシロ
キサン組成物。1. A composition capable of being cured by both a moisture curing mechanism and a radical polymerization curing mechanism, wherein the composition has the following general formula: (In the formula, R 1 and R 3 are divalent hydrocarbon groups, R 2 and R 4
Represents a monovalent hydrocarbon group, X represents a hydroxyl group or a hydrolyzable group, k is an integer of 0 to 4, m is an integer of 50 to 10000, and a is 0 or 1). And (b) a condensation reaction product of a compound having at least one vinyl group which is a radical polymerization functional group in one molecule and having a group capable of reacting with an amino group, and (c) a radical polymerization initiator and moisture curing. A radical polymerization curable and moisture curable organopolysiloxane composition comprising a catalyst.
ル酸、その無水物またはその酸ハロゲン化物である請求
項１記載の組成物。2. The composition according to claim 1, wherein the compound B is acrylic acid or methacrylic acid, an anhydride thereof or an acid halide thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16522592A JP3328956B2 (en) | 1992-05-14 | 1992-05-14 | Silicone composition curable by moisture and radical polymerization |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16522592A JP3328956B2 (en) | 1992-05-14 | 1992-05-14 | Silicone composition curable by moisture and radical polymerization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05320517A true JPH05320517A (en) | 1993-12-03 |
| JP3328956B2 JP3328956B2 (en) | 2002-09-30 |
Family
ID=15808239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16522592A Expired - Fee Related JP3328956B2 (en) | 1992-05-14 | 1992-05-14 | Silicone composition curable by moisture and radical polymerization |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3328956B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07145323A (en) * | 1993-11-22 | 1995-06-06 | Three Bond Co Ltd | Photocurable and moisture-curable silicone composition |
| JPH09132714A (en) * | 1995-11-08 | 1997-05-20 | Three Bond Co Ltd | Curable organopolysiloxane composition and its production |
| US6262216B1 (en) | 1998-10-13 | 2001-07-17 | Affymetrix, Inc. | Functionalized silicon compounds and methods for their synthesis and use |
| CN105778512A (en) * | 2016-03-31 | 2016-07-20 | 苏州天山新材料技术有限公司 | Environment-friendly dealcoholized room-temperature vulcanized silicone rubber and preparation method thereof |
-
1992
- 1992-05-14 JP JP16522592A patent/JP3328956B2/en not_active Expired - Fee Related
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07145323A (en) * | 1993-11-22 | 1995-06-06 | Three Bond Co Ltd | Photocurable and moisture-curable silicone composition |
| JPH09132714A (en) * | 1995-11-08 | 1997-05-20 | Three Bond Co Ltd | Curable organopolysiloxane composition and its production |
| US6262216B1 (en) | 1998-10-13 | 2001-07-17 | Affymetrix, Inc. | Functionalized silicon compounds and methods for their synthesis and use |
| US6410675B2 (en) | 1998-10-13 | 2002-06-25 | Affymetrix, Inc. | Functionalized silicon compounds and methods for their synthesis and use |
| US6429275B2 (en) | 1998-10-13 | 2002-08-06 | Affymetrix, Inc. | Functionalized silicon compounds and methods for their synthesis and use |
| US6486287B2 (en) | 1998-10-13 | 2002-11-26 | Affymetrix, Inc. | Functionalized silicon compounds and methods for their synthesis and use |
| US6486286B1 (en) | 1998-10-13 | 2002-11-26 | Affymetrix, Inc. | Use of hexahydrolupulones as antibacterial agents |
| US6743882B2 (en) | 1998-10-13 | 2004-06-01 | Affymetrix, Inc. | Functionalized silicon compounds and methods for their synthesis and use |
| US7098286B2 (en) | 1998-10-13 | 2006-08-29 | Affymetrix, Inc. | Functionalized silicon compounds and methods for their synthesis and use |
| US7125947B2 (en) | 1998-10-13 | 2006-10-24 | Affymetrix, Inc. | Functionalized silicon compounds and methods for their synthesis and use |
| US7129307B2 (en) | 1998-10-13 | 2006-10-31 | Affymetrix, Inc. | Functionalized silicon compounds and methods for their synthesis and use |
| CN105778512A (en) * | 2016-03-31 | 2016-07-20 | 苏州天山新材料技术有限公司 | Environment-friendly dealcoholized room-temperature vulcanized silicone rubber and preparation method thereof |
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|---|---|
| JP3328956B2 (en) | 2002-09-30 |
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