JP2954602B2 - Method for producing hydrolyzable silicon group-containing polyoxyalkylene polymer - Google Patents
Method for producing hydrolyzable silicon group-containing polyoxyalkylene polymerInfo
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- JP2954602B2 JP2954602B2 JP21415289A JP21415289A JP2954602B2 JP 2954602 B2 JP2954602 B2 JP 2954602B2 JP 21415289 A JP21415289 A JP 21415289A JP 21415289 A JP21415289 A JP 21415289A JP 2954602 B2 JP2954602 B2 JP 2954602B2
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- JP
- Japan
- Prior art keywords
- group
- unsaturated group
- polyoxyalkylene polymer
- hydrolyzable silicon
- unsaturated
- Prior art date
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Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は加水分解性珪素基含有ポリオキシアルキレン
重合体の製造方法に関する。Description: TECHNICAL FIELD The present invention relates to a method for producing a hydrolyzable silicon-containing polyoxyalkylene polymer.
［従来の技術］ 不飽和基を有するポリオキシアルキレン重合体は、不
飽和基の反応を利用して加水分解性珪素基などの他の官
能基を導入することによって非常に柔軟な硬化性組成物
を得ることができ、シーリング材等の原料として有用で
ある。この場合、硬化物に柔軟性を持たせるためにはポ
リオキシアルキレン重合体として高分子量体のものを用
いる必要がある。[Prior Art] A polyoxyalkylene polymer having an unsaturated group is a very flexible curable composition by introducing another functional group such as a hydrolyzable silicon group using the reaction of an unsaturated group. And useful as a raw material such as a sealing material. In this case, it is necessary to use a high molecular weight polyoxyalkylene polymer in order to impart flexibility to the cured product.
しかし従来提案されているKOHのようなアルカリ触媒
を用いてアルキレンオキシドの重合を行ない、末端のア
ルコキシド基と、アリルクロリドなどの不飽和基含有活
性ハロゲン化合物とを反応させて末端不飽和基含有ポリ
オキシアルキレン重合体を得る方法では、ポリオキシア
ルキレン重合体の分子量が3,000を越えると、副生する
不飽和モノオールの量が増え、実質的な官能基数の低
下、分子量分布の拡大をもたらし、目的とする硬化性組
成物を得ることはできない。However, polymerization of alkylene oxide is carried out using an alkali catalyst such as KOH, which has been conventionally proposed, and a terminal alkoxide group is reacted with an active halogen compound having an unsaturated group such as allyl chloride to form a terminal unsaturated group-containing polymer. In the method for obtaining an oxyalkylene polymer, if the molecular weight of the polyoxyalkylene polymer exceeds 3,000, the amount of unsaturated monool produced as a by-product increases, resulting in a substantial decrease in the number of functional groups and an increase in the molecular weight distribution. Cannot be obtained.
これらの問題点の解消を目的として特開昭50−149797
による方法が提案されたが、ポリオキシアルキレン重合
体同士の分子鎖延長反応という複雑な反応工程を要す
る、分子量分布が広くなる、などの点で不充分なもので
あった。To solve these problems, Japanese Patent Laid-Open No. 50-149797 has been proposed.
Have been proposed, but these methods are insufficient in that a complicated reaction process such as a molecular chain extension reaction between polyoxyalkylene polymers is required and the molecular weight distribution is widened.
また特開昭61−215623によって有機アルミニウム化合
物とポルフィリンとを反応させて得られる錯体触媒を用
いてリビング重合によりアルキレンオキシドの重合を行
い、高分子量で分子量分布の狭い末端不飽和基含有ポリ
オキシアルキレン重合体を得る方法が提案されている。Further, an alkylene oxide is polymerized by living polymerization using a complex catalyst obtained by reacting an organoaluminum compound with porphyrin according to JP-A-61-215623 to obtain a polyoxyalkylene having a terminal unsaturated group having a high molecular weight and a narrow molecular weight distribution. Methods for obtaining polymers have been proposed.
しかし触媒として用いられる金属ポリフィリン錯体の
影響でポリオキシアルキレン重合体が着色するなどの問
題点があり、現実的ではない。However, there is a problem that the polyoxyalkylene polymer is colored due to the influence of the metal porphyrin complex used as a catalyst, which is not practical.
［問題点を解決するための手段］ 本発明者らは前述の問題点を解決すべく検討した結
果、複合金属シアン化物錯体触媒を用いて不飽和基を有
しないモノエポキシドを開環重合させた後、不飽和基含
有モノエポキシドを共重合することにより、分子鎖の末
端に不飽和基を導入でき、高分子量体で分子量分布が狭
く、しかも着色等が少ない実用性の高い不飽和基含有ポ
リオキシアルキレン重合体が得られ、不飽和基を加水分
解性珪素基に変換することにより、柔軟な硬化性組成物
を与える加水分解性末端基含有ポリオキシアルキレン重
合体が得られることを見出した。[Means for Solving the Problems] As a result of studying to solve the above problems, the present inventors conducted ring-opening polymerization of a monoepoxide having no unsaturated group using a double metal cyanide complex catalyst. Thereafter, by copolymerizing an unsaturated group-containing monoepoxide, an unsaturated group can be introduced into the terminal of the molecular chain, and a high molecular weight polymer having a narrow molecular weight distribution and a high degree of practical use having a high degree of uncolored unsaturated group-containing polyepoxide. It has been found that an oxyalkylene polymer is obtained, and a polyoxyalkylene polymer having a hydrolyzable terminal group that gives a flexible curable composition can be obtained by converting an unsaturated group into a hydrolyzable silicon group.
すなわち本発明は、複合金属シアン化物錯体触媒を用
いてイニシエーターの存在下、不飽和基を有しない炭素
数３以上のモノエポキシドの開環重合を行った後、不飽
和基含有モノエポキシドを共重合させて不飽和基含有ポ
リオキシアルキレン重合体とし、続いて不飽和基を加水
分解性珪素基に変換する、加水分解性珪素基含有ポリオ
キシアルキレン重合体の製造方法を提供するものであ
る。That is, in the present invention, after performing ring-opening polymerization of a monoepoxide having 3 or more carbon atoms having no unsaturated group in the presence of an initiator using a double metal cyanide complex catalyst, the unsaturated group-containing monoepoxide is copolymerized. An object of the present invention is to provide a method for producing a hydrolyzable silicon group-containing polyoxyalkylene polymer, which comprises polymerizing an unsaturated group-containing polyoxyalkylene polymer and subsequently converting the unsaturated group into a hydrolyzable silicon group.
本発明で用いられる不飽和基を有しない炭素数３以上
のモノエポキシドとしては、プロピレンオキシド、1,2
−ブチレンオキシド、エピクロルヒドリンなどの脂肪族
アルキレンオキシド、スチレンオキシドのような芳香族
アルキレンオキシドなどを挙げることができるが、脂肪
族アルキレンオキシドが好ましく、特にプロピレンオキ
シドが好ましい。不飽和基含有モノエポキシドとして
は、アリルグリシジルエーテル、グリシジルアクリレー
ト、グリシジルメタクリレートが好ましい。The monoepoxide having 3 or more carbon atoms having no unsaturated group used in the present invention includes propylene oxide, 1,2
Examples thereof include aliphatic alkylene oxides such as -butylene oxide and epichlorohydrin, and aromatic alkylene oxides such as styrene oxide. Aliphatic alkylene oxides are preferable, and propylene oxide is particularly preferable. As the unsaturated group-containing monoepoxide, allyl glycidyl ether, glycidyl acrylate, and glycidyl methacrylate are preferable.
本発明において使用される複合金属シアン化物錯体は
一般に次のような構造を有し、これを用いてポリエーテ
ル類を得ることも知られている。The double metal cyanide complex used in the present invention generally has the following structure, and it is also known that polyethers can be obtained using the same.
Ma・Ｍ′・（CN）ｂ・（H2O）ｄ・（Ｒ）ｅ・（MX）
ｆ ［US Pat 3278457,3278458,3278459,3427256,3427334,3
427335］ この触媒を用いると、不飽和モノオールの含量の少な
いきわめて高分子量のポリエーテル類を製造することが
可能である。 M a · M '· (CN ) b · (H 2 O) d · (R) e · (MX)
f [US Pat 3278457,3278458,3278459,3427256,3427334,3
427335] With this catalyst, it is possible to produce very high molecular weight polyethers with a low content of unsaturated monols.
本発明で用いられるイニシエーターとしては多価アル
コール、多価フェノール、多価カルボン酸などの多価活
性水素含有化合物、不飽和アルコール、不飽和フェノー
ル、不飽和カルボン酸などの不飽和基含有活性水素含有
化合物などが用いうる。Examples of the initiator used in the present invention include polyhydric alcohols, polyhydric phenols, polyhydric active hydrogen-containing compounds such as polyhydric carboxylic acids, unsaturated alcohols, unsaturated phenols, and unsaturated carboxylic acid-containing active hydrogens such as unsaturated carboxylic acids. Compounds and the like can be used.
本発明においては、これらイニシエーターに複合金属
シアン化物錯体触媒を用いて、不飽和基を有しない炭素
数３以上のモノエポキシドの開環重合を行った後、不飽
和基含有モノエポキシドを共重合させることにより、分
子鎖に不飽和基を導入できる。In the present invention, after performing ring-opening polymerization of a monoepoxide having no unsaturated group and having 3 or more carbon atoms using a double metal cyanide complex catalyst as the initiator, a monoepoxide having an unsaturated group is copolymerized. By doing so, an unsaturated group can be introduced into the molecular chain.
該ポリオキシアルキレン重合体は分子中に不飽和基と
共に水酸基を有するが、これは必要に応じてブロック
し、活性水素のない形にすることも可能である。そのよ
うな方法としては、酸無水物、酸クロリド等によるエス
テル化、クロルギ酸アルキル等によるカーボネート化、
モノイソシアネートによるウレタン化、トリアルキルシ
リルクロリドやヘキサメチルジシラザン等によるシリル
エーテル化、ハロゲン化アルキル・アリルによるアルキ
ル・アリル化、ジヒドロピラン等のビニルエーテル化合
物によるエーテル化等公知の方法が使用できる。The polyoxyalkylene polymer has a hydroxyl group together with an unsaturated group in the molecule, but this can be blocked if necessary to make it into a form free of active hydrogen. Examples of such a method include esterification with an acid anhydride, acid chloride or the like, carbonate formation with an alkyl chloroformate or the like,
Known methods such as urethanization with a monoisocyanate, silyl etherification with a trialkylsilyl chloride or hexamethyldisilazane, alkyl / allylation with an alkyl / allyl halide, and etherification with a vinyl ether compound such as dihydropyran can be used.
不飽和基含有ポリオキシアルキレン重合体の不飽和基
の加水分解性珪素基への変換はSi−Ｈ基を有する化合物
の不飽和基への付加反応によって得られる。本付加反応
は公知のヒドロシリル化触媒（例えば白金担持活性炭や
塩化白金酸）を用いて達成される。Conversion of the unsaturated group of the unsaturated group-containing polyoxyalkylene polymer to a hydrolyzable silicon group can be obtained by an addition reaction of a compound having a Si-H group to the unsaturated group. This addition reaction is achieved using a known hydrosilylation catalyst (for example, activated carbon carrying platinum or chloroplatinic acid).
本発明で使用されるヒドロシラン化合物としては一般
式X3-aRaSiH（Ｘはハロゲン原子、アルコキシ基、アル
ケノキシ基、アシルオキシ基、アミド基、アミノオキシ
基、ケトキシメート基から選択される基、Ｒは炭素数１
〜６のアルキル基、ａは０、１または２）で示される化
合物であり、例えばメチルジメトキシシラン、メチルジ
エトキシシランのようなアルキルジアルコキシシラン
類、トリメトキシシラン、トリエトキシシランのような
トリアルコキシシラン類、ジメチルエトキシシランのよ
うなジアルキルアルコキシシラン類、トリクロロシラ
ン、メチルジクロロシラン等のアルキルハロゲノシラン
類等が使用できる。アルキルハロゲノシラン類のハロゲ
ン原子は不飽和基に付加した後に公知の方法で例えばカ
ルボン酸、オキシム、アミド、ヒドロキシルアミン等の
活性水素化合物やケトン類のアルカリ金属エノラートと
反応させてもよい。The hydrosilane compound used in the present invention includes a compound represented by the general formula X3 - aR a SiH (X is a group selected from a halogen atom, an alkoxy group, an alkenoxy group, an acyloxy group, an amide group, an aminooxy group, a ketoximate group, Is 1 carbon
And a is a compound represented by 0, 1 or 2), for example, alkyldialkoxysilanes such as methyldimethoxysilane and methyldiethoxysilane, and tris such as trimethoxysilane and triethoxysilane. Alkoxysilanes, dialkylalkoxysilanes such as dimethylethoxysilane, and alkylhalogenosilanes such as trichlorosilane and methyldichlorosilane can be used. After the halogen atom of the alkylhalogenosilane is added to the unsaturated group, the halogen atom may be reacted with an active hydrogen compound such as a carboxylic acid, oxime, amide, or hydroxylamine, or an alkali metal enolate of a ketone by a known method.
本方法で合成した加水分解性珪素基含有ポリオキシア
ルキレン重合体は、大気中の湿分により常温で硬化し、
柔軟でしかも伸びの大きな硬化物を与えることがわかっ
た。The hydrolyzable silicon group-containing polyoxyalkylene polymer synthesized by the present method is cured at room temperature by atmospheric moisture,
It was found to give a cured product that is flexible and has a large elongation.
［作用］ 本発明においては、加水分解性珪素基含有ポリオキシ
アルキレン重合体を製造するに当り、複合金属シアン化
物錯体触媒を用いて不飽和基を含有しないモノエポキシ
ドの開環重合を行った後、不飽和基含有モノエポキシド
の開環重合を行ない、次いで、不飽和基を加水分解性珪
素基に変換する。これによりはじめて、高分子量で副生
成物が少なく、分子量分布の狭い不飽和基含有ポリオキ
シアルキレン重合体を実用的に製造することが可能とな
る。[Action] In the present invention, in producing the hydrolyzable silicon group-containing polyoxyalkylene polymer, after performing ring-opening polymerization of an unsaturated group-free monoepoxide using a double metal cyanide complex catalyst, The ring-opening polymerization of the unsaturated group-containing monoepoxide is carried out, and then the unsaturated group is converted into a hydrolyzable silicon group. This makes it possible for the first time to practically produce an unsaturated group-containing polyoxyalkylene polymer having a high molecular weight, few by-products and a narrow molecular weight distribution.
［実施例］ （実施例１） 耐圧反応容器中でアリルアルコールと亜鉛ヘキサシア
ノコバルテートとの混合物にプロピレンオキシドを少し
ずつ導入しながら110℃で反応させ、アリルアルコール
１モルあたりプロピレンオキシド300モルを付加させ
た。続いて混合物にアリルアルコール１モルあたり、ア
リルグリシジルエーテル2.0モルを添加して反応させ
た。反応後混合物にナトリウムメトキシドのメタノール
溶液を加えて80℃に加熱攪拌し、塩酸水溶液で中和して
から脱水、脱メタノールを行ない、濾過した。[Example] (Example 1) A mixture of allyl alcohol and zinc hexacyanocobaltate was allowed to react at 110 ° C in a pressure-resistant reaction vessel while introducing propylene oxide little by little, and 300 mol of propylene oxide was added per 1 mol of allyl alcohol. I let it. Subsequently, 2.0 mol of allyl glycidyl ether was added to 1 mol of allyl alcohol and reacted. After the reaction, a methanol solution of sodium methoxide was added to the mixture, and the mixture was heated and stirred at 80 ° C., neutralized with an aqueous hydrochloric acid solution, dehydrated, demethanol removed, and filtered.
得られた不飽和基含有ポリオキシアルキレン重合体は
GPCによる分析で数平均分子量17500、分子量分布（Mw/M
n）は1.15であった。またヨウ素価で測定した不飽和度
は0.11ミリ当量/gであった。The resulting unsaturated group-containing polyoxyalkylene polymer is
GPC analysis showed a number average molecular weight of 17,500 and a molecular weight distribution (M w / M
n ) was 1.15. The degree of unsaturation measured by the iodine value was 0.11 meq / g.
該不飽和基含有ポリオキシアルキレン重合体に、塩化
白金酸の溶液（イソプロピルアルコール／テトラヒドロ
フラン）を添加し、不飽和基と等当量のメチルジメトキ
シシランを加え、80℃で反応させた。得られた加水分解
性珪素基含有ポリオキシアルキレン重合体にジブチル錫
ジラウレート１％を添加し、室温に放置し、硬化物を得
た。硬化物の物性は50％モジュラスが0.90kg/cm2、伸び
が650％であった。A solution of chloroplatinic acid (isopropyl alcohol / tetrahydrofuran) was added to the unsaturated group-containing polyoxyalkylene polymer, and an equivalent of methyldimethoxysilane was added to the unsaturated group, followed by reaction at 80 ° C. 1% of dibutyltin dilaurate was added to the obtained hydrolyzable silicon group-containing polyoxyalkylene polymer, and the mixture was allowed to stand at room temperature to obtain a cured product. Physical properties of the cured product were a 50% modulus of 0.90 kg / cm 2 , and an elongation of 650%.
（実施例２） 実施例１と同様の方法で、トリプロピレングリコール
をイニシエーターとして、プロピレンオキシドの重合を
行なった後、アリルグリシジルエーテルをトリプロピレ
ングリコール１モルに対し、３モル添加して反応させ
た。反応終了後、ナトリウムメトキシドのメタノール溶
液を加え加熱攪拌後、塩酸水溶液で中和し、脱水、脱メ
タノールを行った後、濾過した。(Example 2) In the same manner as in Example 1, polymerization of propylene oxide was performed using tripropylene glycol as an initiator, and then 3 mol of allyl glycidyl ether was added to 1 mol of tripropylene glycol to cause a reaction. Was. After completion of the reaction, a methanol solution of sodium methoxide was added, and the mixture was heated and stirred, neutralized with an aqueous hydrochloric acid solution, dehydrated, demethanol removed, and then filtered.
得られた不飽和基含有ポリオキシアルキレン重合体の
数平均分子量15000、分子量分布（Mw/Mn）は1.10であっ
た。またヨウ素価で測定した不飽和度は0.21ミリ当量/g
であった。The obtained unsaturated group-containing polyoxyalkylene polymer had a number average molecular weight of 15,000 and a molecular weight distribution (M w / M n ) of 1.10. The degree of unsaturation measured by iodine value is 0.21 meq / g
Met.
該不飽和基含有ポリオキシアルキレン重合体に、塩化
白金酸の溶液（イソプロピルアルコール／テトラヒドロ
フラン）を添加し、不飽和基と等当量のメチルジメトキ
シシランを加え、80℃で反応させた。得られた加水分解
性珪素基含有ポリオキシアルキレン重合体にジブチル錫
ジラウレート１％を添加し、室温に放置し、硬化物を得
た。硬化物の物性は50％モジュラスが1.20kg/cm2、伸び
が580％であった。A solution of chloroplatinic acid (isopropyl alcohol / tetrahydrofuran) was added to the unsaturated group-containing polyoxyalkylene polymer, and an equivalent of methyldimethoxysilane was added to the unsaturated group, followed by reaction at 80 ° C. 1% of dibutyltin dilaurate was added to the obtained hydrolyzable silicon group-containing polyoxyalkylene polymer, and the mixture was allowed to stand at room temperature to obtain a cured product. Physical properties of the cured product were a 50% modulus of 1.20 kg / cm 2 , and an elongation of 580%.
［発明の効果］ 以上示したように、複合金属シアン化物錯体触媒を用
いて不飽和基を有しない炭素数３以上のモノエポキシド
を開環重合した後、不飽和基含有モノエポキシドを共重
合して、分子内に不飽和基を有する高分子量で分子量分
布の狭いポリオキシアルキレン重合体とし、不飽和基を
加水分解性珪素基に変換することにより、柔軟でしかも
伸びのある硬化物を与える加水分解性珪素基含有ポリオ
キシアルキレン重合体が得られることが明らかとなっ
た。該重合体は、シーリング材等に有用である。[Effects of the Invention] As described above, after ring-opening polymerization of an unsaturated group-free monoepoxide having 3 or more carbon atoms using a double metal cyanide complex catalyst, an unsaturated group-containing monoepoxide is copolymerized. A polyoxyalkylene polymer having a high molecular weight and a narrow molecular weight distribution having an unsaturated group in the molecule, and converting the unsaturated group into a hydrolyzable silicon group to obtain a flexible and stretchable cured product. It became clear that a decomposable silicon group-containing polyoxyalkylene polymer was obtained. The polymer is useful as a sealing material and the like.
Claims (3)
シエーターの存在下、不飽和基を有しない炭素数３以上
のモノエポキシドの開環重合を行った後、不飽和基含有
モノエポキシドを共重合させて不飽和基含有ポリオキシ
アルキレン重合体とし、続いて不飽和基を加水分解性珪
素基に変換する、加水分解性珪素基含有ポリオキシアル
キレン重合体の製造方法。1. An unsaturated group-free monoepoxide having 3 or more carbon atoms is subjected to ring-opening polymerization in the presence of an initiator using a double metal cyanide complex catalyst. A method for producing a hydrolyzable silicon group-containing polyoxyalkylene polymer, which comprises polymerizing an unsaturated group-containing polyoxyalkylene polymer, and subsequently converting the unsaturated group into a hydrolyzable silicon group.
ルコキシ基、アルケノキシ基、アシルオキシ基、アミド
基、アミノオキシ基、ケトキシメート基から選択される
基、Ｒは炭素数１〜６のアルキル基、ａは０、１または
２）で示される有機珪素化合物を不飽和基に付加させる
ことにより、不飽和基を加水分解性珪素基に変換する請
求項１に記載の製造方法。2. A compound of the general formula X 3-a R a SiH wherein X is a group selected from a halogen atom, an alkoxy group, an alkenoxy group, an acyloxy group, an amide group, an aminooxy group and a ketoximate group, 2. The production method according to claim 1, wherein the alkyl group of 6, a is converted to a hydrolyzable silicon group by adding an organosilicon compound represented by 0, 1 or 2) to the unsaturated group.
または末端不飽和基含有活性水素含有化合物である請求
項１または２に記載の製造方法。3. The method according to claim 1, wherein the initiator is a polyvalent active hydrogen-containing compound or a terminal unsaturated group-containing active hydrogen-containing compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21415289A JP2954602B2 (en) | 1989-08-22 | 1989-08-22 | Method for producing hydrolyzable silicon group-containing polyoxyalkylene polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21415289A JP2954602B2 (en) | 1989-08-22 | 1989-08-22 | Method for producing hydrolyzable silicon group-containing polyoxyalkylene polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0379627A JPH0379627A (en) | 1991-04-04 |
| JP2954602B2 true JP2954602B2 (en) | 1999-09-27 |
Family
ID=16651086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21415289A Expired - Fee Related JP2954602B2 (en) | 1989-08-22 | 1989-08-22 | Method for producing hydrolyzable silicon group-containing polyoxyalkylene polymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2954602B2 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0747630B2 (en) * | 1989-11-06 | 1995-05-24 | ユニオン・カーバイド・ケミカルズ・アンド・プラスチツクス・カンパニー・インコーポレーテツド | Silicone polyether copolymer surfactant |
| DE10136446A1 (en) * | 2001-07-26 | 2003-02-06 | Bayer Ag | Production of polyalkylene oxide for use, e.g. as elastomers, involves polymerisation of a mixture of saturated epoxide, unsaturated epoxide and optionally other epoxides in presence of multi-metal cyanide catalyst |
| US7781559B2 (en) | 2003-08-01 | 2010-08-24 | Cemedine Co., Ltd. | Curable composition and method for producing the same |
| JP4575010B2 (en) * | 2004-03-25 | 2010-11-04 | 株式会社カネカ | Novel functional group-containing polyoxyalkylene polymer and production method |
| KR101354835B1 (en) | 2005-12-02 | 2014-01-22 | 모멘티브 파포만스 마테리아루즈 쟈판 고도가이샤 | Room temperature curable silicon group-containing polymer composition |
| US20070299242A1 (en) * | 2006-06-21 | 2007-12-27 | Bayer Materialscience Llc | Pendant acrylate and/or methacrylate-containing polyether monols and polyols |
| CN104350084B (en) | 2012-05-31 | 2016-10-12 | 株式会社钟化 | There is the polymer of the end structure having multiple reactive silicon and manufacture method thereof and utilization |
| US9969843B2 (en) | 2012-05-31 | 2018-05-15 | Kaneka Corporation | Polymer having terminal structure including plurality of reactive silicon groups, method for manufacturing same, and use for same |
| JP2014101529A (en) * | 2014-03-13 | 2014-06-05 | Nippon Zeon Co Ltd | Polyether polymer |
| JP6222155B2 (en) * | 2015-04-06 | 2017-11-01 | 日本ゼオン株式会社 | Polyether polymer |
| JP2016194081A (en) * | 2016-06-15 | 2016-11-17 | 日本ゼオン株式会社 | Polyether polymer |
-
1989
- 1989-08-22 JP JP21415289A patent/JP2954602B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0379627A (en) | 1991-04-04 |
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