JPH0711155A - Moisture-curable composition - Google Patents
Moisture-curable compositionInfo
- Publication number
- JPH0711155A JPH0711155A JP15941393A JP15941393A JPH0711155A JP H0711155 A JPH0711155 A JP H0711155A JP 15941393 A JP15941393 A JP 15941393A JP 15941393 A JP15941393 A JP 15941393A JP H0711155 A JPH0711155 A JP H0711155A
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- Japan
- Prior art keywords
- moisture
- group
- weight
- curable composition
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Silicon Polymers (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、接着性、耐水接着性に
優れた湿気硬化性組成物に関する。FIELD OF THE INVENTION The present invention relates to a moisture-curable composition having excellent adhesiveness and water-resistant adhesiveness.
【０００２】[0002]
【従来の技術】１液型の湿気硬化性ゴムとしては、シリ
コーンゴム、ウレタンゴム、ポリサルファイドゴム等が
知られている。１液型の湿気硬化性ゴムは、一般に硬化
が速く２液型のものに比べ、液の混合調製等の必要がな
い等作業性の点で優れている。2. Description of the Related Art Silicone rubber, urethane rubber, polysulfide rubber and the like are known as one-pack type moisture curable rubber. The one-pack type moisture-curable rubber is generally quicker to cure and is superior to the two-pack type in terms of workability such as the need for mixing and preparing liquids.
【０００３】[0003]
【発明が解決しようとする課題】しかし、シリコン系ゴ
ムのものは、周囲への汚染の可能性、表面への塗装性の
点で問題があり、ウレタン系ゴムのものは、貯蔵安定
性、耐候性、耐発泡性、変色等の点で問題がある。さら
に、ポリサルフィド系ゴムについても、硬化性、周囲へ
の汚染の可能性の点で問題がある。変成シリコーンポリ
マーとして室温硬化型の組成物が知られている。これ
は、ポリエーテルを主鎖とする架橋可能な加水分解性シ
リコン官能基を有する重合体であり、硬化触媒を用いて
密封下では長期間安定であるが、湿気にさらすと急速に
硬化してゴム状物質に変わる１液型組成物である（特公
昭６２−３５４２１号公報、特開昭６１−１４１７６１
号公報、特開平１−５８２１９号公報）。この重合体
は、ポリウレタン系に比べ貯蔵安定性、耐候性、耐発泡
性、変色性が良好であり、ポリサルファイド系に比べ、
硬化性に優れ、周囲への汚染性が少なく、毒性がない。
また、通常のシリコーン系に比べ周囲への汚染性が少な
く、表面への塗装性が良好である。この加水分解性ケイ
素を有する重合体の硬化触媒として、チタン酸エステル
化合物、錫カルボン酸塩化合物、アミン類等が知られて
いるが、これらの触媒では、接着性、特に、耐水接着性
が著しく劣り、プライマー等を使用する必要がある。特
開昭５７−１８２３５０号公報でアルコキシシランの使
用が提案されているが、十分な効果がえられない。However, the silicone rubber has a problem in the possibility of contamination to the surroundings and the coating property on the surface, and the urethane rubber has the problems of storage stability and weather resistance. There are problems with respect to properties, foaming resistance, discoloration, etc. Further, the polysulfide-based rubber also has problems in terms of curability and the possibility of contamination of the surroundings. Room-temperature curable compositions are known as modified silicone polymers. It is a polymer with cross-linkable hydrolyzable silicone functional groups with a polyether backbone, which is stable for a long period of time under seal with a curing catalyst, but cures rapidly when exposed to moisture. It is a one-pack type composition which is changed to a rubber-like substance (Japanese Patent Publication No. 62-35421, JP-A No. 61-141761).
Japanese Patent Laid-Open No. 1-58219). This polymer has better storage stability, weather resistance, foaming resistance and discoloration resistance than the polyurethane type, and compared with the polysulfide type,
It has excellent curability, little pollution to the surroundings, and no toxicity.
In addition, it has less contamination to the surroundings and good coatability on the surface as compared with ordinary silicone type. Titanic acid ester compounds, tin carboxylate compounds, amines, etc. are known as curing catalysts for the polymer having hydrolyzable silicon, but these catalysts have remarkable adhesiveness, especially water-resistant adhesiveness. Inferior, it is necessary to use a primer or the like. JP-A-57-182350 proposes the use of alkoxysilanes, but the sufficient effect cannot be obtained.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、耐水性お
よび接着性を有する湿気硬化性組成物について検討し、
本発明に至った。すなわち、本発明は、（ａ）分子内に
少なくとも１つの加水分解性ケイ素含有基を含む有機重
合体１００重量部、（ｂ）アミノ基置換アルコキシシラ
ン化合物または／およびその誘導体０．２〜２０重量
部、（ｃ）硬化触媒として下記式（Ｉ）The present inventors have investigated a moisture-curable composition having water resistance and adhesiveness,
The present invention has been completed. That is, the present invention includes (a) 100 parts by weight of an organic polymer containing at least one hydrolyzable silicon-containing group in the molecule, (b) 0.2 to 20 parts by weight of an amino group-substituted alkoxysilane compound or a derivative thereof. Part, (c) as a curing catalyst, the following formula (I)
【０００５】[0005]
【化２】 [Chemical 2]
【０００６】（式中、Ｒ1 、Ｒ2 、Ｒ3 およびＲ4 は、
炭素原子数１〜１０の炭化水素で、それぞれＲ1 〜Ｒ4
が同一であっても、異なっていてもよい。）で示される
化合物０．１〜１０重量部を配合してなる湿気硬化性組
成物を提供する。(Wherein R 1 , R 2 , R 3 and R 4 are
Hydrocarbons having 1 to 10 carbon atoms, R 1 to R 4 respectively
May be the same or different. The present invention provides a moisture-curable composition containing 0.1 to 10 parts by weight of the compound represented by the formula (1).
【０００７】以下に、本発明を詳細に説明する。本発明
に用いる有機重合体は、分子内に少なくとも１つの加水
分解性ケイ素含有基を含み、主鎖としては、アルキレン
オキシド重合体、ポリエーテル、エーテル・エステルブ
ロック共重合体が挙げられる。また、ビニル系またはジ
エン系の化合物、アクリル酸エステル、メタクリル酸エ
ステルが挙げられる。ポリエーテルとしては、The present invention will be described in detail below. The organic polymer used in the present invention contains at least one hydrolyzable silicon-containing group in the molecule, and examples of the main chain include alkylene oxide polymers, polyethers, and ether / ester block copolymers. Further, vinyl-based or diene-based compounds, acrylic acid esters, and methacrylic acid esters may be mentioned. As a polyether,
【０００８】[0008]
【化３】 [Chemical 3]
【０００９】が例示され、また、ビニル系化合物として
は、具体的には、ポリブタジエン、スチレン−ブタジエ
ン共重合体、アクリロニトリル−ブタジエン共重合体、
エチレン−ブタジエン共重合体、エチレン−プロピレン
共重合体、エチレン−酢酸ビニル共重合体、エチレン−
アクリル酸エステル共重合体、ポリイソプレン、スチレ
ン−イソプレン共重合体、イソブチレン−イソプレン共
重合体、ポリクロロプレン、スチレン−クロロプレン共
重合体、アクリロニトリル−クロロプレン共重合体、ポ
リイソブチレン、ポリアクリル酸エステル、ポリメタク
リル酸エステルなどが挙げられる。Examples of the vinyl compound include polybutadiene, styrene-butadiene copolymer, acrylonitrile-butadiene copolymer, and
Ethylene-butadiene copolymer, ethylene-propylene copolymer, ethylene-vinyl acetate copolymer, ethylene-
Acrylic ester copolymer, polyisoprene, styrene-isoprene copolymer, isobutylene-isoprene copolymer, polychloroprene, styrene-chloroprene copolymer, acrylonitrile-chloroprene copolymer, polyisobutylene, polyacrylic ester, poly Examples thereof include methacrylic acid ester.
【００１０】加水分解性ケイ素含有基は、たとえば、ケ
イ素原子と結合した加水分解性基を有するケイ素含有基
やシラノール基のように湿気や架橋剤の存在下、必要に
応じて触媒などを使用することにより縮合反応を起こす
基のことであり、分子内の末端に存在していても、側鎖
に存在していてもよく、具体的には、ハロゲン化シリル
基、アルコキシシリル基、アルケニルオキシシリル基、
アシロキシシリル基、アミノシリル基、アミノオキシシ
リル基、オキシムシリル基、アミドシリル基が挙げら
れ、これらは具体的に構造式で示すと、As the hydrolyzable silicon-containing group, for example, a catalyst is used, if necessary, in the presence of moisture or a crosslinking agent, such as a silicon-containing group having a hydrolyzable group bonded to a silicon atom or a silanol group. It is a group which causes a condensation reaction, and may be present at the terminal or in the side chain in the molecule. Specifically, it is specifically a halogenated silyl group, an alkoxysilyl group, an alkenyloxysilyl group. Base,
Examples thereof include an acyloxysilyl group, an aminosilyl group, an aminooxysilyl group, an oximesilyl group and an amidosilyl group, and when these are specifically shown by a structural formula,
【００１１】[0011]
【化４】 [Chemical 4]
【００１２】等が挙げられる。特に、取扱が容易である
点でアルコキシシリル基が好ましい。さらに、本発明で
用いる有機重合体の数平均分子量は、特に制約はない
が、高分子のものは高粘度であり、硬化性組成物とした
場合、使用上困難となるため、３００００以下が望まし
い。このような有機重合体は、公知の方法によって製造
することができるが、鐘淵化学工業（株）製のカネカＭ
Ｓポリマー等の市販品を使用してもよい。And the like. In particular, an alkoxysilyl group is preferable because it is easy to handle. Further, the number average molecular weight of the organic polymer used in the present invention is not particularly limited, but a polymer having a high viscosity has a high viscosity and is difficult to use in the case of a curable composition. . Such an organic polymer can be produced by a known method, but Kaneka M manufactured by Kanegafuchi Chemical Industry Co., Ltd.
You may use a commercial item, such as S polymer.
【００１３】本発明に用いるアミノ基置換アルコキシシ
ラン化合物またはその誘導体は、例えば、Ｈ2 ＮＣＨ2
ＣＨ2 ＣＨ2 Ｓｉ（ＯＣＨ 3）3 ，Ｈ2 ＮＣＨ2 ＣＨ2
ＣＨ 2 Ｓｉ（ＯＣ2 Ｈ5 ）3 ，Ｈ2 ＮＣＨ2 ＣＨ2 ＮＨ
ＣＨ2 ＣＨ2 ＣＨ2 Ｓｉ（ＯＣＨ3 ）3 ，Ｈ2 ＮＣＨ2
ＣＨ2 ＮＨＣＨ2 ＣＨ2 ＣＨ2 Ｓｉ（ＯＣ2 Ｈ5 ）3，Amino group-substituted alkoxy group used in the present invention
The orchid compound or its derivative is, for example, H2NCH2
CH2CH2Si (OCH3)3, H2NCH2CH2
CH 2Si (OC2HFive)3, H2NCH2CH2NH
CH2CH2CH2Si (OCH3)3, H2NCH2
CH2NHCH2CH2CH2Si (OC2HFive)3，
【００１４】[0014]
【化５】 等のアミノ基置換アルコキシシラン、および、上記アミ
ノ基置換アルコキシシランと[Chemical 5] An amino group-substituted alkoxysilane such as
【００１５】[0015]
【化６】 [Chemical 6]
【００１６】の様なメタクリルオキシシラン化合物との
反応物が挙げられるが、これに限定されるものではな
い。また、単独のアミノ基置換アルコキシシラン化合
物、またはその誘導体であっても、アルコキシシラン化
合物およびその誘導体の内の２種以上の混合物の形態で
もよい。このようなアミノ基置換アルコキシシラン化合
物は、公知の方法によって製造することができるが、日
本ユニカー（株）製等の市販品を使用することもでき
る。上記のアミノ基置換アルコキシシラン化合物の含有
量は、０．２〜２０重量部、特に０．４〜１０重量部で
あるのが好ましい。０．２未満では、接着性が期待でき
ず、２０重量部超では、ゲル化など貯蔵中の安定性に問
題がある。Examples thereof include a reaction product with a methacryloxysilane compound, but are not limited thereto. Further, it may be a single amino group-substituted alkoxysilane compound or a derivative thereof, or a mixture of two or more kinds of the alkoxysilane compound and a derivative thereof. Such an amino group-substituted alkoxysilane compound can be produced by a known method, but a commercially available product such as manufactured by Nippon Unicar Co., Ltd. can also be used. The content of the above amino group-substituted alkoxysilane compound is preferably 0.2 to 20 parts by weight, particularly 0.4 to 10 parts by weight. If it is less than 0.2, adhesiveness cannot be expected, and if it exceeds 20 parts by weight, there is a problem in stability during storage such as gelation.
【００１７】さらに、アミノ基置換アルコキシシラン化
合物に対して、メタクリルオキシシラン化合物を反応さ
せた誘導体は、さらに好ましい接着性および貯蔵中の安
定性を得ることができる。メタクリルシラン化合物とア
ミノ基置換アルコキシシランを１６０℃程度までの温度
で能動的に反応させたもの、あるいは、メタクリルシラ
ン化合物の単純な添加であってもよい。Further, a derivative obtained by reacting an amino group-substituted alkoxysilane compound with a methacryloxysilane compound can obtain more preferable adhesiveness and stability during storage. A methacrylsilane compound and an amino group-substituted alkoxysilane may be actively reacted at a temperature up to about 160 ° C., or a simple addition of a methacrylsilane compound may be used.
【００１８】本発明に用いる硬化触媒として式（Ｉ）The curing catalyst used in the present invention has the formula (I)
【００１９】[0019]
【化７】 [Chemical 7]
【００２０】で示される化合物が用いられる。式中、Ｒ
1 、Ｒ2 、Ｒ3 およびＲ4 は、炭素原子数１〜１０の炭
化水素で、それぞれＲ1 〜Ｒ4 が同一であっても、異な
っていてもよい。このような硬化触媒は、公知の方法に
より製造し得るが、日東化成（株）製のＵ３０３等を利
用することも可能である。硬化触媒の含有量は、湿気硬
化性組成物１００重量部に対して、０．１〜２０重量
部、特に、０．５〜１０重量部であるのが好ましい。
０．１重量部未満では、硬化性に問題があり、２０重量
部超では、貯蔵中の安定性に問題がある。The compounds represented by are used. Where R
1 , R 2 , R 3 and R 4 are hydrocarbons having 1 to 10 carbon atoms, and R 1 to R 4 may be the same or different. Such a curing catalyst can be manufactured by a known method, but U303 or the like manufactured by Nitto Kasei Co., Ltd. can also be used. The content of the curing catalyst is preferably 0.1 to 20 parts by weight, particularly 0.5 to 10 parts by weight, based on 100 parts by weight of the moisture curable composition.
If it is less than 0.1 part by weight, there is a problem in curability, and if it exceeds 20 parts by weight, there is a problem in stability during storage.
【００２１】本発明の湿気硬化性組成物には、さらに、
充填剤、可塑剤、着色剤、硬化促進剤、硬化遅延剤、タ
レ防止剤、老化防止剤など湿気硬化性組成物に通常添加
される添加剤を加えてもよい。例えば、充填剤として
は、炭酸カルシウム、二酸化チタン、カオリン、タル
ク、シリカ、等が挙げられる。可塑剤としては、ジオク
チルフタレート（ＤＯＰ）、ブチルベンジルフタレート
等が挙げられる。タレ防止剤としては、水添ヒマシ油、
有機ベントナイト、コロイド状シリカ等が挙げられる。
得られた組成物は、実質的に水分の存在しない状態で調
製した後、密封下に貯蔵される。貯蔵期間中は、硬化は
進行せず、これを容器から取り出し大気に曝すことによ
り、すみやかに表面より硬化が進行するので建造物、自
動車、船舶、土木工事等の弾性シーリング材として有用
であり、更に注型ゴム、型取り用材料、塗料、接着剤と
しても使用できる。The moisture curable composition of the present invention further comprises
Additives usually added to the moisture-curable composition such as a filler, a plasticizer, a colorant, a curing accelerator, a curing retarder, an anti-sagging agent and an anti-aging agent may be added. For example, the filler includes calcium carbonate, titanium dioxide, kaolin, talc, silica and the like. Examples of the plasticizer include dioctyl phthalate (DOP) and butylbenzyl phthalate. As an anti-sagging agent, hydrogenated castor oil,
Examples include organic bentonite and colloidal silica.
The composition obtained is prepared in a substantially water-free state and then stored under a sealed condition. During the storage period, curing does not proceed, and it is useful as an elastic sealing material for buildings, automobiles, ships, civil engineering works, etc., because curing proceeds from the surface immediately by removing it from the container and exposing it to the atmosphere, Further, it can be used as a cast rubber, a molding material, a paint, and an adhesive.
【００２２】[0022]
【実施例】以下に、実施例を用いて、具体的に説明する
が、これによって本発明の範囲を限定するものではな
い。 （実施例１〜８）表１に示される組成成分の組成物を混
練し、ＪＩＳ Ａ５７５８に準拠し、引張接着性を試験
した。被着体は、アルミニウム板を使用した。 （比較例１〜４）表１に示される組成成分の組成物を混
練し、ＪＩＳ Ａ５７５８に準拠し、引張接着性を試験
した。被着体は、アルミニウム板を使用した。EXAMPLES The present invention will be specifically described below with reference to examples, but the scope of the present invention is not limited thereby. (Examples 1 to 8) Compositions having the composition components shown in Table 1 were kneaded and tested for tensile adhesion in accordance with JIS A5758. An aluminum plate was used as the adherend. (Comparative Examples 1 to 4) Compositions having the composition components shown in Table 1 were kneaded and tested for tensile adhesion in accordance with JIS A5758. An aluminum plate was used as the adherend.
【００２３】[0023]
【表１】 [Table 1]
【００２４】[0024]
【表２】 [Table 2]
【００２５】 注）表中、組成物成分の量は、重量部を示す。 ＭＳポリマー２０Ａ：鐘淵化学工業（株）製の加水分解
性ケイ素含有基を含む有機重合体Note) In the table, the amounts of the composition components are parts by weight. MS Polymer 20A: Organic polymer containing hydrolyzable silicon-containing group manufactured by Kanegafuchi Chemical Industry Co., Ltd.
【００２６】[0026]
【化８】 [Chemical 8]
【００２７】平均分子量 約８０００ 炭酸カルシウム：白石工業（株）製の炭酸カルシウム
（白艶華、ＣＣＲ） 二酸化チタン：石原産業（株）製の二酸化チタン（Ｒ−
８２０） ノクラックＮＳ−６：大内新興化学工業（株）製の老化
防止剤 ビニルアルコキシシラン化合物：日本ユニカー（株）製
のＡ−１７１ アミノ基置換アルコキシシラン化合物 Ａ−１１２０：日本ユニカー（株）製 Ａ−１１００：日本ユニカー（株）製 合成例１および２として合成したアミノ基置換アルコキ
シシラン化合物の組成を表２に示す。なお、反応条件
は、窒素雰囲気下、１４０℃で、１０時間反応させた。Average molecular weight of about 8000 Calcium carbonate: Calcium carbonate manufactured by Shiroishi Industry Co., Ltd. (white luster, CCR) Titanium dioxide: Titanium dioxide manufactured by Ishihara Sangyo Co., Ltd. (R-
820) Nocrac NS-6: Antiaging agent manufactured by Ouchi Shinko Chemical Co., Ltd. Vinylalkoxysilane compound: A-171 Amino group-substituted alkoxysilane compound manufactured by Nippon Unicar Co., Ltd. A-1120: Nippon Unicar Co., Ltd. Manufactured A-1100: manufactured by Nippon Unicar Co., Ltd. Table 2 shows the compositions of amino group-substituted alkoxysilane compounds synthesized as Synthesis Examples 1 and 2. The reaction conditions were 140 ° C. and 10 hours of reaction in a nitrogen atmosphere.
【００２８】 [0028]
【００２９】触媒 （Ｃ4 Ｈ9 ）2 Ｓｎ〔ＯＳｉ（ＯＣ
2 Ｈ5 ）3 〕2 ：日東化成（株）製のＵ３０３ 破断状況は、以下の略号で示した。 ＣＦ：材料破断 ＴＣＦ：材料薄層破断 ＡＦ：被着体−材料界面剥離Catalyst (C 4 H 9 ) 2 Sn [OSi (OC
2 H 5 ) 3 ] 2 : U303 manufactured by Nitto Kasei Co., Ltd. The breakage conditions are indicated by the following abbreviations. CF: Material rupture TCF: Material thin layer rupture AF: Adherend-material interface peeling
【００３０】表１の結果から、実施例１は、ほとんどア
ミノ基置換アルコキシシラン化合物の添加されていない
比較例４に比べ、引張接着性に優れていることがわか
る。また、特定の硬化触媒を用いている本発明の組成物
は、他の硬化触媒を用いる比較例に比べ通常の接着性に
優れるばかりではなく、耐水接着性にも優れている。From the results shown in Table 1, it can be seen that Example 1 is superior in tensile adhesiveness to Comparative Example 4 in which almost no amino group-substituted alkoxysilane compound is added. Further, the composition of the present invention using a specific curing catalyst is excellent not only in ordinary adhesiveness but also in water-resistant adhesiveness as compared with Comparative Examples using other curing catalysts.
【００３１】[0031]
【発明の効果】本発明の湿気硬化性組成物を用いると、
接着性、特に、耐水接着性および貯蔵時の安定性に優れ
ている。さらに、このような湿気硬化性組成物は、シー
リング剤、コーティング剤、弾性接着剤として有用に用
いられる。When the moisture-curable composition of the present invention is used,
Excellent adhesion, especially water-resistant adhesion and stability during storage. Furthermore, such a moisture curable composition is usefully used as a sealing agent, a coating agent, and an elastic adhesive.
Claims (1)
性ケイ素含有基を含む有機重合体１００重量部、 （ｂ）アミノ基置換アルコキシシラン化合物または／お
よびその誘導体０．２〜２０重量部、 （ｃ）硬化触媒として下記式（Ｉ） 【化１】 （式中、Ｒ1 、Ｒ2 、Ｒ3 およびＲ4 は、炭素原子数１
〜１０の炭化水素で、それぞれＲ1 〜Ｒ4 が同一であっ
ても、異なっていてもよい。）で示される化合物０．１
〜１０重量部を配合してなることを特徴とする湿気硬化
性組成物。1. (a) 100 parts by weight of an organic polymer containing at least one hydrolyzable silicon-containing group in the molecule, (b) 0.2 to 20 parts by weight of an amino group-substituted alkoxysilane compound or / and its derivative. (C) as a curing catalyst, the following formula (I): (In the formula, R 1 , R 2 , R 3 and R 4 have 1 carbon atom.
In hydrocarbons of 10 to 10, R 1 to R 4 may be the same or different. ) Compound 0.1
A moisture-curable composition comprising 10 to 10 parts by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15941393A JP2868690B2 (en) | 1993-06-29 | 1993-06-29 | Moisture curable composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15941393A JP2868690B2 (en) | 1993-06-29 | 1993-06-29 | Moisture curable composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0711155A true JPH0711155A (en) | 1995-01-13 |
| JP2868690B2 JP2868690B2 (en) | 1999-03-10 |
Family
ID=15693212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15941393A Expired - Lifetime JP2868690B2 (en) | 1993-06-29 | 1993-06-29 | Moisture curable composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2868690B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011089878A1 (en) | 2010-01-19 | 2011-07-28 | 株式会社カネカ | Curable composition |
-
1993
- 1993-06-29 JP JP15941393A patent/JP2868690B2/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011089878A1 (en) | 2010-01-19 | 2011-07-28 | 株式会社カネカ | Curable composition |
| US9023932B2 (en) | 2010-01-19 | 2015-05-05 | Kaneka Corporation | Curable composition |
| JP5744759B2 (en) * | 2010-01-19 | 2015-07-08 | 株式会社カネカ | Curable composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2868690B2 (en) | 1999-03-10 |
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