JPH0977781A - Silane having radically polymerizable group - Google Patents
Silane having radically polymerizable groupInfo
- Publication number
- JPH0977781A JPH0977781A JP7262170A JP26217095A JPH0977781A JP H0977781 A JPH0977781 A JP H0977781A JP 7262170 A JP7262170 A JP 7262170A JP 26217095 A JP26217095 A JP 26217095A JP H0977781 A JPH0977781 A JP H0977781A
- Authority
- JP
- Japan
- Prior art keywords
- group
- integer
- silane
- radically polymerizable
- polymerizable group
- Prior art date
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Abstract
(57)【要約】
【課題】 水溶性を有し、しかも、水溶液中での加水分
解速度が遅いが故に安定性に優れたラジカル重合性基を
有する新規なシラン化合物を提供すること。
【解決手段】一般式
［式中、Ａはカルボニルオキシ基又はフェニレン基、Ｒ
1は水素原子又はメチル基、Ｒ2はエーテル結合を含んで
もよい２価炭化水素基、Ｒ3は水素原子又は炭素原子数
１〜１０の１価炭化水素基、Ｒ4は炭素原子数１〜１０
の１価炭化水素基、ｌは０又は１の整数、ｍは０又は１
の整数、ｎは１〜２の整数、ｌ＋ｎは１〜３の整数であ
る。ｐは３〜５０の整数である。］で示されるラジカル
重合性基を有するシラン。(57) [PROBLEMS] To provide a novel silane compound having a radically polymerizable group which is water-soluble and has excellent stability because of its slow hydrolysis rate in an aqueous solution. SOLUTION: General formula [In the formula, A is a carbonyloxy group or a phenylene group, R is
1 is a hydrogen atom or a methyl group, R 2 is a divalent hydrocarbon group which may include an ether bond, R 3 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and R 4 is 1 to 1 carbon atoms. 10
A monovalent hydrocarbon group, l is an integer of 0 or 1, m is 0 or 1.
, N is an integer of 1 to 2, and l + n is an integer of 1 to 3. p is an integer of 3 to 50. ] The silane which has a radically polymerizable group shown by these.
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、水溶性を有し、水
溶液安定性に優れるラジカル重合性基を有する新規なシ
ラン化合物に関する。TECHNICAL FIELD The present invention relates to a novel silane compound having a radically polymerizable group which is water-soluble and has excellent stability in an aqueous solution.
【０００２】[0002]
【従来の技術】従来、重合性ビニル単量体と重合性ビニ
ル基含有シラン化合物とのラジカル重合反応により共重
合させて得られたポリマーを水に希釈しエマルジョン化
する試みがなされていたが、エマルジョンの安定性は有
限であり長期保存は不可能であった。2. Description of the Related Art Conventionally, attempts have been made to dilute a polymer obtained by copolymerizing a polymerizable vinyl monomer and a polymerizable vinyl group-containing silane compound by a radical polymerization reaction in water to form an emulsion. Emulsion stability was finite and long-term storage was not possible.
【０００３】また、他の水系化する手法として乳化重合
や懸濁重合が知られているが、これらの重合反応では、
アルコキシシリル基等の加水分解基が共重合中または保
存中に加水分解し架橋してしまう為、増粘あるいはゲル
化が起こり易い。従って、安定性に欠け長期保存をする
ことが同様に不可能であった。Emulsion polymerization and suspension polymerization are known as other water-based methods. In these polymerization reactions,
Since a hydrolyzable group such as an alkoxysilyl group is hydrolyzed and cross-linked during copolymerization or storage, thickening or gelation easily occurs. Therefore, it lacked stability and could not be stored for a long period of time.
【０００４】[0004]
【発明が解決しようとする課題】本発明は、上記問題点
に鑑みなされた発明であり、水溶性を有し、水溶液中で
の加水分解速度が遅いが故に安定性に優れたラジカル重
合性基を有する新規なシラン化合物を提供することを目
的とするものである。DISCLOSURE OF THE INVENTION The present invention has been made in view of the above problems, and is a radically polymerizable group which is water-soluble and has excellent stability due to its slow hydrolysis rate in an aqueous solution. It is an object of the present invention to provide a novel silane compound having
【０００５】[0005]
【課題を解決するための手段】すなわち、本発明は、一
般式「化２」That is, the present invention has the general formula "Chemical formula 2".
【化２】 ［式中、Ａはカルボニルオキシ基又はフェニレン基、Ｒ
1は水素原子又はメチル基、Ｒ2はエーテル結合を含んで
もよい２価炭化水素基、Ｒ3は水素原子又は炭素原子数
１〜１０の１価炭化水素基、Ｒ4は炭素原子数１〜１０
の１価炭化水素基、ｌは０又は１の整数、ｍは０又は１
の整数、ｎは１〜２の整数、ｌ＋ｎは１〜３の整数であ
る。ｐは３〜５０の整数である。］で示されるラジカル
重合性基を有するシランを提供するものである。Embedded image [In the formula, A is a carbonyloxy group or a phenylene group, R is
1 is a hydrogen atom or a methyl group, R 2 is a divalent hydrocarbon group which may include an ether bond, R 3 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and R 4 is 1 to 1 carbon atoms. 10
A monovalent hydrocarbon group, l is an integer of 0 or 1, m is 0 or 1.
, N is an integer of 1 to 2, and l + n is an integer of 1 to 3. p is an integer of 3 to 50. ] The silane which has a radically polymerizable group shown by these is provided.
【０００６】また、本発明は、分子内にエチレンオキサ
イド基を６０ｗｔ％以上有する上記記載のラジカル重合
性基を有するシランを提供するものである。The present invention also provides a silane having a radically polymerizable group as described above, which has 60 wt% or more of ethylene oxide group in the molecule.
【０００７】上記一般式において、Ａはカルボニルオキ
シ基又はフェニレン基を表し、Ｒ1は水素原子又はメチ
ル基である。In the above general formula, A represents a carbonyloxy group or a phenylene group, and R 1 is a hydrogen atom or a methyl group.
【０００８】Ｒ2は２価炭化水素基（直鎖若くは分枝で
ありその水素原子の一部若くは全部がハロゲン置換され
てもよく、又はエーテル結合を含んでも良い）好ましく
は炭素数３〜１０であり、−（ＣＨ2）x−（ｘは１以上
の整数）、−（ＣＨ2ＣＨ2Ｏ）y（ＣＨ2）z−（ｙは１
以上の整数、ｚは０以上の整数）及びこれらの一部が分
岐しているものが例示され、具体的には、 CH2CH2CH2、CH2CH2CH2CH2CH2CH2、CH2CH2OCH2CH2CH2、C
H2CH2OCH2CH2OCH2CH2CH2、CH2CH2OCH2CH2OCH2CH2CH2CH2
CH2CH2、CH2CH2OC(CH3)HCH2OCH2CH2CH2CH2、C(CH3)HCH2
OCH2CH2OCH2CH2CH2、などが例示される。R 2 is a divalent hydrocarbon group (which may be linear or branched and some or all of its hydrogen atoms may be halogen-substituted, or may contain an ether bond), preferably having 3 carbon atoms. a ~10, - (CH 2) x - (x is an integer of 1 or more), - (CH 2 CH 2 O) y (CH 2) z - (y 1
The above integers, z is an integer greater than or equal to 0), and some of these are branched. Specifically, CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 OCH 2 CH 2 CH 2 , C
H 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 CH 2 , CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 CH 2 CH 2
CH 2 CH 2 , CH 2 CH 2 OC (CH 3 ) HCH 2 OCH 2 CH 2 CH 2 CH 2 , C (CH 3 ) HCH 2
OCH 2 CH 2 OCH 2 CH 2 CH 2 , and the like are exemplified.
【０００９】Ｒ3は水素原子、炭素原子数１〜１０の１
価炭化水素基であり、直鎖状でも分岐していてもよい。
特に有用なものは、水素原子、メチル基、エチル基であ
る。R 3 is hydrogen atom, 1 having 1 to 10 carbon atoms
It is a valent hydrocarbon group, which may be linear or branched.
Particularly useful are a hydrogen atom, a methyl group and an ethyl group.
【００１０】Ｒ4は炭素原子数１〜１０の１価炭化水素
基であり、直鎖状でも分岐していてもよい。特に有用な
ものは、メチル基である。R 4 is a monovalent hydrocarbon group having 1 to 10 carbon atoms, which may be linear or branched. Particularly useful is the methyl group.
【００１１】ｌは０又は１の整数、ｍは０又は１の整
数、ｎは１〜２の整数である。１＋ｎは１〜３の整数で
あり、特に、１＋ｎが２以下であることが好ましい。ｐ
は３〜５０好ましくは３〜２０の整数である。ｐが３未
満であると水溶性が乏しくなり、ｐが５０をこえると原
料が固体となり取扱いが難しくなる。L is an integer of 0 or 1, m is an integer of 0 or 1, and n is an integer of 1 to 2. 1 + n is an integer of 1 to 3, and 1 + n is preferably 2 or less. p
Is an integer of 3 to 50, preferably 3 to 20. When p is less than 3, water solubility is poor, and when p exceeds 50, the raw material becomes solid and handling becomes difficult.
【００１２】上記一般式「化２」で表される水溶性を有
するラジカル重合性基を有するシラン化合物の具体例を
以下に示す。Specific examples of the water-soluble radically polymerizable group-containing silane compound represented by the above general formula "Chemical Formula 2" are shown below.
【００１３】[0013]
【化３】 Embedded image
【００１４】[0014]
【化４】 Embedded image
【００１５】[0015]
【化５】 Embedded image
【００１６】[0016]
【化６】 [Chemical 6]
【００１７】[0017]
【化７】 [Chemical 7]
【００１８】[0018]
【化８】 Embedded image
【００１９】[0019]
【化９】 Embedded image
【００２０】[0020]
【化１０】 Embedded image
【００２１】[0021]
【化１１】 Embedded image
【００２２】[0022]
【化１２】 [Chemical 12]
【００２３】[0023]
【化１３】 Embedded image
【００２４】[0024]
【化１４】 この中でも［化３］、［化４］、［化５］、［化１１］
が好ましい。Embedded image Among these, [Chemical formula 3], [Chemical formula 4], [Chemical formula 5], [Chemical formula 11]
Is preferred.
【００２５】また、以下の［化１５］〜［化１７］に示
すようなｐが３未満のものは、水溶性、水溶液安定性が
乏しくなる。If p is less than 3 as shown in the following [Chemical formula 15] to [Chemical formula 17], the water solubility and the stability of the aqueous solution become poor.
【化１５】 [Chemical 15]
【００２６】[0026]
【化１６】 Embedded image
【００２７】[0027]
【化１７】 Embedded image
【００２８】本発明のシラン化合物において、エチレン
オキサイド基を６０ｗｔ％以上含有するものは、高い水
溶性が得られるため、本発明の好ましい態様である。例
えば、上記に例示した「化３」〜「化１４」のシラン化
合物は、エチレンオキサイド基を６０ｗｔ％以上含有
し、高い水溶性が得られる。Among the silane compounds of the present invention, those containing an ethylene oxide group in an amount of 60 wt% or more are a preferred embodiment of the present invention because high water solubility is obtained. For example, the silane compounds of "Chemical Formula 3" to "Chemical Formula 14" illustrated above contain 60 wt% or more of ethylene oxide groups, and high water solubility is obtained.
【００２９】ラジカル重合性基を有する本発明のシラン
は、相応するラジカル重合性基含有クロロシランとグリ
コールとを塩基性条件下での脱塩酸反応、又は、相応す
るラジカル重合性基含有アルコキシシランとグリコール
とを酸性触媒若くは塩基触媒又は有機金属触媒存在下で
のアルコール交換反応により製造することができる。反
応の際、必要に応じてＢＨＴ等の重合禁止剤を添加して
もよい。The silane of the present invention having a radical-polymerizable group is a dehydrochlorination reaction of a corresponding radical-polymerizable group-containing chlorosilane and a glycol under basic conditions, or a corresponding radical-polymerizable group-containing alkoxysilane and a glycol. And can be produced by an alcohol exchange reaction in the presence of an acidic catalyst or a base catalyst or an organometallic catalyst. During the reaction, a polymerization inhibitor such as BHT may be added if necessary.
【００３０】[0030]
【実施例】以下に本発明の実施例を説明する。Embodiments of the present invention will be described below.
【００３１】［実施例１］「化３」のシラン化合物の製
造 冷却菅、温度計、滴下漏斗を付した５００ｍｌの４つ口
フラスコにメタクロキシプロピルトリクロロシラン１０
０ｇ（０．３８ｍｏｌ）を仕込み攪拌した。内温９０℃
まで昇温後、メチルトリグリコール１２５．４ｇ（０．
７７ｍｏｌ）を滴下したところフラスコ内が７０℃まで
低下した。さらに、９０℃にて１時間攪拌後、メチルト
リグリコール９４．１ｇ（０．５７ｍｏｌ）と尿素３
４．４ｇ（０．５７ｍｏｌ）を添加し９０℃にて３時間
熟成した。熟成後、反応混合液を分離して尿素塩酸塩を
除去し、得られた生成物をプロピオンオキシド０．５ｇ
で中和した。中和後、活性炭０．８ｇを用いて浮遊する
尿素塩酸塩を除去し、ろ過後ストリップしたところ１５
５．２ｇの無色透明な液体が得られた。この液体を1Ｈ
−ＮＭＲスペクトル及びＩＲスペクトルで分析したとこ
ろ上記化合物であることが確認された。分析結果を表１
及び表２に示す。また、この化合物の水溶性及び水溶液
安定性を試験し、その結果を表３に示した。[Example 1] Production of silane compound of "Chemical formula 3" Methacryloxypropyltrichlorosilane 10 was placed in a 500 ml four-necked flask equipped with a cooling tube, a thermometer and a dropping funnel.
0 g (0.38 mol) was charged and stirred. Inner temperature 90 ° C
After heating up to 125.4 g of methyltriglycol (0.
(77 mol) was added dropwise, and the temperature inside the flask dropped to 70 ° C. Furthermore, after stirring at 90 ° C. for 1 hour, 94.1 g (0.57 mol) of methyltriglycol and 3 parts of urea were added.
4.4 g (0.57 mol) was added and the mixture was aged at 90 ° C. for 3 hours. After aging, the reaction mixture was separated to remove urea hydrochloride, and the obtained product was added with 0.5 g of propion oxide.
Neutralized. After neutralization, the floating urea hydrochloride was removed by using 0.8 g of activated carbon, and the product was filtered and stripped.
5.2 g of a colorless transparent liquid was obtained. 1 H for this liquid
It was confirmed that the above compound was obtained by analysis by NMR spectrum and IR spectrum. The analysis results are shown in Table 1.
And Table 2. Further, the water solubility and aqueous solution stability of this compound were tested, and the results are shown in Table 3.
【００３２】[0032]
【化１８】 ＮＭＲEmbedded image NMR
【表１】 [Table 1]
【００３３】ＩＲ分析IR analysis
【表２】 [Table 2]
【００３４】［実施例２］「化４」のシラン化合物の製
造 冷却菅、温度計、滴下漏斗及びエステルアダプターを付
した２００ｍｌの４つ口フラスコにスチリルトリメトキ
シシラン４４．８ｇ（０．２０ｍｏｌ）、メチルトリグ
リコール１０３．３ｇ（０．６３ｍｏｌ）、ＢＨＴ０．
２ｇ及びテトラブチルチタネート０．０４ｇを仕込み攪
拌した。内温１１０℃まで徐々に昇温を行い、流出して
くるメタノールを溜去した。溜去し終わった後、１１０
℃にて２時間攪拌しストリップしたところ淡黄色透明の
液体が１２５．８ｇ得られた。実施例１と同様に1Ｈ−
ＮＭＲ及びＩＲにて構造確認を行った。また、その水溶
性及び水溶液安定性を試験しその結果を表３に示した。Example 2 Production of Silane Compound of “Chemical Formula 4” 44.8 g (0.20 mol) of styryltrimethoxysilane was placed in a 200 ml four-necked flask equipped with a cooling pipe, a thermometer, a dropping funnel and an ester adapter. , 103.3 g (0.63 mol) of methyltriglycol, BHT0.
2 g and tetrabutyl titanate 0.04 g were charged and stirred. The internal temperature was gradually raised to 110 ° C., and the methanol flowing out was distilled off. After distilling off, 110
When the mixture was stirred at 0 ° C. for 2 hours and stripped, 125.8 g of a pale yellow transparent liquid was obtained. 1 H-as in Example 1
The structure was confirmed by NMR and IR. Further, its water solubility and aqueous solution stability were tested, and the results are shown in Table 3.
【００３５】［実施例３〜１１］［比較例１〜３］ラジ
カル重合性基含有クロロシラン又はアルコキシシランと
グリコールの種類を変えた以外は実施例１又は２と同様
にして、「化９」を除く「化５」〜「化１７」の化合物
を合成し、水溶性及び水溶液安定性について調べた。そ
の結果を表３に示した。[Examples 3 to 11] [Comparative Examples 1 to 3] "Chemical Formula 9" was obtained in the same manner as in Example 1 or 2 except that the types of the radical polymerizable group-containing chlorosilane or alkoxysilane and glycol were changed. Compounds of “Chemical Formula 5” to “Chemical Formula 17”, which were excluded, were synthesized and examined for water solubility and aqueous solution stability. Table 3 shows the results.
【００３６】[0036]
【表３】 ［評価基準］ 水溶性 ：シラン２０部に水８０部を加えて混合
後、外観を観察した。 ○：透明 ；×：白濁又は分離 水溶液安定性：シラン２０部に水８０部を加えて混合し
た水溶液を、２５℃にて１週間放置後外観を観察した。 ○：透明 ；×：白濁又は分離[Table 3] [Evaluation Criteria] Water solubility: 80 parts of water was added to 20 parts of silane and mixed, and then the appearance was observed. ◯: Transparent; ×: White turbidity or separation Aqueous solution stability: An aqueous solution obtained by adding 80 parts of water to 20 parts of silane and mixing the mixture was allowed to stand at 25 ° C. for 1 week, and the appearance was observed. ○: transparent; ×: cloudy or separated
【００３７】［応用例１］実施例１で得られたシラン化
合物「化３」２０ｇを１００ｍｌのナスフラスコに入
れ、窒素雰囲気下スターラーを用いて攪拌した。オイル
バスの温度を１５０℃に保ち１時間攪拌したところ増粘
がみられた。このものをＧＰＣ分析（スタンダード：ポ
リスチレン）したところ数平均分子量８４００であっ
た。これに水８０ｇを注ぎ込んだところ均一な溶液とな
った。[Application Example 1] 20 g of the silane compound "Chemical Formula 3" obtained in Example 1 was placed in a 100 ml eggplant flask and stirred under a nitrogen atmosphere using a stirrer. When the temperature of the oil bath was kept at 150 ° C. and the mixture was stirred for 1 hour, thickening was observed. When this product was subjected to GPC analysis (standard: polystyrene), the number average molecular weight was 8400. When 80 g of water was poured into this, a uniform solution was obtained.
【００３８】［応用例２］冷却菅、温度計、滴下漏斗を
付した５００ｍｌの４つ口フラスコに実施例１で得られ
たシラン化合物「化３」３０ｇ、Ｎ，Ｎ−ジメチルアク
リルアミド３５ｇ、メタクリル酸メチル３５ｇ、アセト
ン１５０ｇ及びアゾビスイソブチルニトリル３ｇを仕込
み窒素雰囲気下６０℃で１０時間重合を行った後、アセ
トンを減圧溜去したところ、数平均分子量１２２００
（ＧＰＣ分析）の固体状の重合物が得られた。この重合
物は、実施例１と同様な水溶性及び水溶液安定性試験を
行ったところ、いずれも良好な結果を示した。また、１
０％水溶液へガラス板を浸漬し１週間室温下乾燥した被
膜は水に不要であり、シラン架橋により耐水性が付与さ
れていることが分かった。[Application Example 2] 30 g of the silane compound "Chemical Formula 3" obtained in Example 1, 35 g of N, N-dimethylacrylamide and methacryl were placed in a 500 ml four-necked flask equipped with a cooling tube, a thermometer and a dropping funnel. When 35 g of methyl acidate, 150 g of acetone and 3 g of azobisisobutylnitrile were charged and polymerization was carried out at 60 ° C. for 10 hours in a nitrogen atmosphere, acetone was distilled off under reduced pressure to give a number average molecular weight of 12,200.
A solid polymer (GPC analysis) was obtained. When this polymer was tested for water solubility and aqueous solution stability in the same manner as in Example 1, all showed good results. Also, 1
It was found that the coating film obtained by immersing a glass plate in a 0% aqueous solution and drying it at room temperature for 1 week was not necessary for water, and that the silane crosslinking imparted water resistance.
【００３９】[0039]
【発明の効果】本発明によれば、上記の実施例から、水
溶性および水溶液安定性に優れたシラン化合物を得るこ
とができる。また、応用例１からラジカル重合性に富
み、且つ重合体も水溶性に優れたシラン化合物を得るこ
とができる。さらに、応用例２から本発明のシラン化合
物は、湿分硬化型の水溶性被覆組成物の原料として有用
であることが分かる。According to the present invention, a silane compound excellent in water solubility and aqueous solution stability can be obtained from the above examples. Further, from Application Example 1, it is possible to obtain a silane compound which is rich in radical polymerizability and whose polymer is also excellent in water solubility. Furthermore, Application Example 2 shows that the silane compound of the present invention is useful as a raw material for a moisture-curable water-soluble coating composition.
【００４０】本発明のシラン化合物は、ラジカル重合性
基を有するので、単独の重合体または他の水溶性を有す
るビニル単量体と共重合体を形成することにより、水溶
性を有する優れた表面被覆剤となることが出来、しかも
加水分解基を有するので無機基剤と結合可能である。し
たがって、本発明のシラン化合物を用いれば、耐候性、
防汚性、離型性、潤滑性に優れた被覆組成物を提供で
き、具体的には、海中防汚塗料、耐候性塗料、建築用撥
水剤、金型離型剤、毛髪化粧料などの用途に応用可能で
ある。Since the silane compound of the present invention has a radical-polymerizable group, it is possible to form a homopolymer or a copolymer with another water-soluble vinyl monomer to obtain an excellent water-soluble surface. It can be used as a coating agent, and since it has a hydrolyzable group, it can bind to an inorganic base material. Therefore, by using the silane compound of the present invention, weather resistance,
It is possible to provide a coating composition having excellent antifouling property, releasability and lubricity, and specifically, underwater antifouling paint, weather resistant paint, water repellent for construction, mold release agent, hair cosmetics, etc. It can be applied to
───────────────────────────────────────────────────── フロントページの続き (72)発明者 山本 昭 群馬県碓氷郡松井田町大字人見１番地10 信越化学工業株式会社シリコーン電子材料 技術研究所内 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Akira Yamamoto 1-10 Hitomi, Matsuida-cho, Usui-gun, Gunma Prefecture Inside the Silicone Electronic Materials Technology Laboratory, Shin-Etsu Chemical Co., Ltd.
Claims (2)
1は水素原子又はメチル基、Ｒ2はエーテル結合を含んで
もよい２価炭化水素基、Ｒ3は水素原子又は炭素原子数
１〜１０の１価炭化水素基、Ｒ4は炭素原子数１〜１０
の１価炭化水素基、ｌは０又は１の整数、ｍは０又は１
の整数、ｎは１〜２の整数、ｌ＋ｎは１〜３の整数であ
る。ｐは３〜５０の整数である。］で示されるラジカル
重合性基を有するシラン。1. A general formula “Chemical Formula 1” [In the formula, A is a carbonyloxy group or a phenylene group, R is
1 is a hydrogen atom or a methyl group, R 2 is a divalent hydrocarbon group which may include an ether bond, R 3 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and R 4 is 1 to 1 carbon atoms. 10
A monovalent hydrocarbon group, l is an integer of 0 or 1, m is 0 or 1.
, N is an integer of 1 to 2, and l + n is an integer of 1 to 3. p is an integer of 3 to 50. ] The silane which has a radically polymerizable group shown by these.
ｔ％以上有する請求項１記載のラジカル重合性基を有す
るシラン。2. An ethylene oxide group having a molecular weight of 60 w
The silane having a radically polymerizable group according to claim 1, which has t% or more.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7262170A JPH0977781A (en) | 1995-09-14 | 1995-09-14 | Silane having radically polymerizable group |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7262170A JPH0977781A (en) | 1995-09-14 | 1995-09-14 | Silane having radically polymerizable group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0977781A true JPH0977781A (en) | 1997-03-25 |
Family
ID=17372043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7262170A Pending JPH0977781A (en) | 1995-09-14 | 1995-09-14 | Silane having radically polymerizable group |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0977781A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150353668A1 (en) * | 2013-01-11 | 2015-12-10 | Cheil Industries Inc. | Photocurable composition, barrier layer comprising same, and encapsulated device comprising same |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5342232A (en) * | 1976-09-29 | 1978-04-17 | Union Carbide Corp | Inorganic oxide granular compositions and resin compositions containing said granular compositions |
| JPS63130613A (en) * | 1986-11-21 | 1988-06-02 | Mitsubishi Petrochem Co Ltd | Solid polyelectrolyte composition |
| JPS63307888A (en) * | 1987-06-08 | 1988-12-15 | Mitsubishi Petrochem Co Ltd | Polymerizable compound |
| JPS6420257A (en) * | 1987-07-13 | 1989-01-24 | Mitsubishi Petrochemical Co | Organic electrolyte composition |
| JPH0195128A (en) * | 1987-10-07 | 1989-04-13 | Nippon Oil Co Ltd | New macromer containing polyether in its side chain |
-
1995
- 1995-09-14 JP JP7262170A patent/JPH0977781A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5342232A (en) * | 1976-09-29 | 1978-04-17 | Union Carbide Corp | Inorganic oxide granular compositions and resin compositions containing said granular compositions |
| JPS63130613A (en) * | 1986-11-21 | 1988-06-02 | Mitsubishi Petrochem Co Ltd | Solid polyelectrolyte composition |
| JPS63307888A (en) * | 1987-06-08 | 1988-12-15 | Mitsubishi Petrochem Co Ltd | Polymerizable compound |
| JPS6420257A (en) * | 1987-07-13 | 1989-01-24 | Mitsubishi Petrochemical Co | Organic electrolyte composition |
| JPH0195128A (en) * | 1987-10-07 | 1989-04-13 | Nippon Oil Co Ltd | New macromer containing polyether in its side chain |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150353668A1 (en) * | 2013-01-11 | 2015-12-10 | Cheil Industries Inc. | Photocurable composition, barrier layer comprising same, and encapsulated device comprising same |
| US9534069B2 (en) * | 2013-01-11 | 2017-01-03 | Cheil Industries, Inc. | Photocurable composition, barrier layer comprising same, and encapsulated device comprising same |
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