JPS59113051A - Room temperature curable composition - Google Patents
Room temperature curable compositionInfo
- Publication number
- JPS59113051A JPS59113051A JP22459282A JP22459282A JPS59113051A JP S59113051 A JPS59113051 A JP S59113051A JP 22459282 A JP22459282 A JP 22459282A JP 22459282 A JP22459282 A JP 22459282A JP S59113051 A JPS59113051 A JP S59113051A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- parts
- silicic acid
- group
- curing catalyst
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C26/00—Coating not provided for in groups C23C2/00 - C23C24/00
Abstract
Description
【発明の詳細な説明】
本発明は、室温硬化性組成物に係り、特に硬化触媒の安
定性が改善されたシリコーン変成ポリエーテル組成物を
提供することに関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to room temperature curable compositions, and more particularly to providing silicone-modified polyether compositions with improved curing catalyst stability.
加水分解性シリコーン官能基を有し、主鎖が本質的にポ
リエーテルである重合体をベースにした室温硬化性組成
物としては１例として、主剤と硬化剤からなる２液型が
知られている。２液型の場合に使用される硬化触媒の中
で、最も一般的な２価の錫化合物は、水分、熱、光なと
に対して不安定であるという欠点をもっている。そのた
め該組成物を、例えばシーラントに応用した場合、表面
の薄層部分の硬化不良を起こすことがあった。As an example of a room temperature curable composition based on a polymer having a hydrolyzable silicone functional group and whose main chain is essentially polyether, a two-component type consisting of a base agent and a curing agent is known. There is. Among the curing catalysts used in the two-component type, the most common divalent tin compound has the disadvantage of being unstable to moisture, heat, and light. Therefore, when the composition is applied, for example, to a sealant, curing failure may occur in the thin layer on the surface.
本発明者らは、この点を改良すへく鋭意検討を重ねた結
果、硬化触媒を含む硬化剤にケイ酸化合物を添加するこ
とにより目的か達せられることを見出し、本発明に到達
した。The present inventors have made extensive studies to improve this point, and as a result, have discovered that the objective can be achieved by adding a silicic acid compound to a curing agent containing a curing catalyst, and have arrived at the present invention.
すなわち本発明は、
（ａ） 架橋可能な加水分解性シリコーン官能基を有
し、主鎖が本質的にポリエーテルである重合体１００重
量部
（ｂ） ケイ酸含有化合物００１〜３０重量部（ｃ）
硬化触媒０．００１〜１０重量部を配合してなる室
温硬化性組成物である。That is, the present invention comprises: (a) 100 parts by weight of a polymer having crosslinkable hydrolyzable silicone functional groups and whose main chain is essentially a polyether; (b) 001 to 30 parts by weight of a silicic acid-containing compound (c) )
This is a room temperature curable composition containing 0.001 to 10 parts by weight of a curing catalyst.
本発明で使用する架橋可能な加水分解性シリコーン官能
基を有し、主鎖が本質的にポリエーテルである重合体と
は、主鎖が本質的に、式％式％（１）
（式中、Ｒ１は炭素数が１〜４である２価のアルキレン
基）
で示される化学的に結合された繰り返［７単位を含み、
かつ加水分解性基と結合したシリコーン原子を有するこ
とにより、湿分の存在下で架橋可能な重合体である。代
表的には末端官能基が、式〔式中、Ｚ Ｌｔ −Ｒ−＋
−ｇｏｇ−＋ −ＲＯＣ−。Polymers having crosslinkable hydrolyzable silicone functional groups and whose main chain is essentially a polyether for use in the present invention are defined as polymers whose main chain is essentially of the formula % (1) (in the formula , R1 is a divalent alkylene group having 1 to 4 carbon atoms) [containing 7 units,
Moreover, it is a polymer that can be crosslinked in the presence of moisture by having a silicone atom bonded to a hydrolyzable group. Typically, the terminal functional group has the formula [wherein Z Lt -R-+
-gog-+ -ROC-.
０ ０ ０
ＩＩ ＩＩ １ｌ−
Ｒ−０−、−ＲＮＨＣ！−及び−Ｃ−（式中、Ｒは同種
又は異種の炭素数１〜２０の２価の炭化水素基）、Ｒ２
は水素又は炭素数１〜２０の置換もしくは非置換の１価
の有機基、Ｒ３は炭素数１〜２０の置換もしくは非置換
の１価の有機基又はオルガノシロキシ基、Ｒ４は炭素数
１〜２０の飽和又は不飽和の１価の炭化水素基、ａはＯ
又は１の整数、ｂは０゜１又は２の整数、Ｃは０，１又
は２の整数、ｍは０〜１８のｌ、Ｘはハロケン基、アル
コキシ基。0 0 0 II II 1l-
R-0-, -RNHC! - and -C- (wherein R is the same or different divalent hydrocarbon group having 1 to 20 carbon atoms), R2
is hydrogen or a substituted or unsubstituted monovalent organic group having 1 to 20 carbon atoms, R3 is a substituted or unsubstituted monovalent organic group having 1 to 20 carbon atoms or an organosiloxy group, and R4 is a substituted or unsubstituted monovalent organic group having 1 to 20 carbon atoms. saturated or unsaturated monovalent hydrocarbon group, a is O
or an integer of 1, b is an integer of 0°1 or 2, C is an integer of 0, 1 or 2, m is 1 of 0 to 18, and X is a haloken group or an alkoxy group.
アルケニルオキシ基、アシロキシ基、アミン基。Alkenyloxy group, acyloxy group, amine group.
アミノオキシ基、オキシム基、ケトオキシム基。Aminooxy group, oxime group, ketoxime group.
アミド基等の加水分解性基又は原子〕で示される重合体
をさす。refers to a polymer represented by a hydrolyzable group or atom such as an amide group.
これらの重合体はｒことえば、末端に、式％式％（３）
（式中、Ｚ ＋ Ｒ２，ａは前記に同し）を有するポリ
エーテルに、式
（式中、Ｒ”、Ｒ４，ｂ、ｃ、ｍ、Ｘは前記に同じ）で
示される化合物を塩化白金酸のような公知のビトロシリ
ル化触楳を用いて室温ないし２００°Ｃで反応させるこ
とにより容易に得ることが出来る。These polymers are composed of a polyether having the formula % (3) (wherein Z + R2, a is the same as above) at the end, and the formula (wherein R'', R4, It can be easily obtained by reacting a compound represented by (b, c, m, X are the same as above) at room temperature to 200°C using a known vitrosilylation catalyst such as chloroplatinic acid.
−トＯ−（式（１））で示される化学的に結合された繰
返し単位には、例えば−０Ｈ２０−、−０Ｈ２０Ｉ（２
０−。-0H20-, -0H20I (2
0-.
？Ｈ３Ｃ２Ｈ５
−ＯＨ−ＣＨ２Ｏ−、ＣＩ−ＴＯＨ２０−、−ＣＨ２０
Ｈ２ＣＨ２０Ｈ２０−などが具体的に挙げられる。これ
らは単独及び混合の形で用いられるが、特にポリオキシ
プロピレンがよい。加水分解性シリコーン官能基は好ま
しくはポリエーテル重合体の末端に存在し、その加水分
解性基としてはアルコキシ基、アシロキン基、アミノ基
、アミノオキシ基、オキシム基、ケトオキシム基、アミ
ド基、アルケニルオキシ基、）＼ロケン基か例示される
。? H3C2H5 -OH-CH2O-, CI-TOH20-, -CH20
Specific examples include H2CH20H20-. These may be used alone or in a mixed form, but polyoxypropylene is particularly preferred. Hydrolyzable silicone functional groups are preferably present at the ends of the polyether polymer, and the hydrolyzable groups include alkoxy groups, acyloquine groups, amino groups, aminooxy groups, oxime groups, ketoxime groups, amide groups, and alkenyloxy groups. Group, )\Loken group is exemplified.
本発明で使用されるケイ酸含有化合物は、例えばカオリ
ン、焼成りレー、パイロフィライト、ベントナイト、セ
リサイト、ゼオライト、ネフエリン・シナイト、タルク
、アタパルジャイト、ワラストナイト、合成ケイ酸アル
ミ、合成ケイ酸カルシウム、ケイソウ土、ケイ石粉、含
水微粉ケイ酸、及び無水微粉ケイ酸がある。特にゼオラ
イトが有効である。The silicic acid-containing compounds used in the present invention include, for example, kaolin, calcined ray, pyrophyllite, bentonite, sericite, zeolite, nepheline sinite, talc, attapulgite, wollastonite, synthetic aluminum silicate, and synthetic silicate. There are calcium, diatomaceous earth, silica powder, hydrous fine silicic acid, and anhydrous fine silicic acid. Zeolite is particularly effective.
これらを含む硬化剤は次のようにして作製することが最
も代表的である。硬化触媒、ケイ酸含有化合物、可塑剤
および充填剤を硬化剤となし、これを主剤に対し概ね、
重量で１０：１になるように添加し、ロール又は高速攪
拌装置で混合する。Curing agents containing these are most typically produced as follows. A curing catalyst, a silicic acid-containing compound, a plasticizer, and a filler are used as curing agents, and these are generally added to the base material.
Add at a ratio of 10:1 by weight and mix on a roll or high speed stirrer.
この場合、充填剤は入れなくてもよく、また必要に応じ
て水添ヒマシ油等のタレ防止剤を添加してもよい。添加
方法は、触媒とケイ酸含有化合物を最初に混ぜた後、残
りの可塑剤、充填剤等を加えても、最初から硬化剤成分
を全て入れて作製してもよいが、前者の方が好ましい。In this case, the filler may not be added, and an anti-sagging agent such as hydrogenated castor oil may be added if necessary. The addition method can be either by first mixing the catalyst and silicic acid-containing compound and then adding the remaining plasticizer, filler, etc., or by adding all the curing agent components from the beginning, but the former method is better. preferable.
シリコーン官能基含有ポリエーテル１００重量部に対し
て、ケイ酸含有化合物は０．０１〜３０重量部の範囲で
使用されるか、好ましくは０１〜１０重量部の範囲で使
用するのがよい。０．０１重量部未満では効果が小さく
、また３０重量部を越えるとモジュラスが高くなるなと
の物性への悪影響か出ることがある。The silicic acid-containing compound is used in an amount of 0.01 to 30 parts by weight, preferably 0.1 to 10 parts by weight, based on 100 parts by weight of the silicone-functional polyether. If it is less than 0.01 parts by weight, the effect will be small, and if it exceeds 30 parts by weight, it may have an adverse effect on physical properties such as increasing the modulus.
本発明で使用する硬化触媒としては、オクチル酸錫、ジ
ブチル錫ジラウレート、ジブチル錫マレエート、ジブチ
ル錫フタレート等のカルボン酸金属塩；有機錫酸化物と
エステルとの反応物；テトラフチルチタネート、オルカ
ッシロキシチタン等の有機チタン酸エステル；アミン類
、アεン塩、４級アンモニウム塩、グアニジン化合物等
が挙げられる。この中で、本発明の効果は、錫系の化合
物、特にオクチル酸錫等の２価の錫系の化合物を硬化触
媒として採用したとき顕著である。これらは単独もしく
は混合して使用できる。これらの硬化触媒は、シリコー
ン官能基含有ポリエーテル１００重量部に対し、０．０
０１〜１０重量部使用するのが好ましい。The curing catalyst used in the present invention includes carboxylic acid metal salts such as tin octylate, dibutyltin dilaurate, dibutyltin maleate, and dibutyltin phthalate; reaction products of organotin oxides and esters; tetraphthyl titanate, and dibutyltin dilaurate; Examples include organic titanate esters such as siloxytitanium; amines, amine salts, quaternary ammonium salts, and guanidine compounds. Among these, the effects of the present invention are remarkable when a tin-based compound, particularly a divalent tin-based compound such as tin octylate, is employed as a curing catalyst. These can be used alone or in combination. These curing catalysts are used in an amount of 0.0 parts by weight per 100 parts by weight of silicone functional group-containing polyether.
It is preferable to use 01 to 10 parts by weight.
本発明を採用したとき、硬化触媒の水分、熱、光に対す
る不安定性は大きく改善され、表面における硬化不良と
いうような現象はなくなる。When the present invention is adopted, the instability of the curing catalyst against moisture, heat, and light is greatly improved, and phenomena such as poor curing on the surface are eliminated.
以下実施例を挙げて具体的に説明する。This will be specifically explained below by giving examples.
比較例１
平均分子量８０００、末端基として、
（ＥＨ３
（（ＩＪ（３０）２Ｓｉ （ｌＪＩ２（Ｊ（２ＣＩ（
２０−基を全末端基のうち８０％有するポリプロピレン
オキシド１００重量部に対し、脂肪酸処理炭酸カルシウ
ム（白石ツノルシウム製、商品名０ＣＲ）１００重量部
、ルチル型酸化チタン２８重量部、エポキシへキサヒド
ロフタル酸ジオクチル３５重量部、ジオクチルフタレー
ト２０重量部、水添化ヒマシ油６重量部、カーホンフラ
ッフ０．５重量部、オリゴエステルアクリレ−１〜（東
亜合成化学製、商品名Ｍ−８０６０）５ Ｎ承部、２．
２−メチレン−ビス−（４−メチル−６−ｔｅｒ−ブチ
ルフェノール）１重量部、２（２−ヒドロキシ−３′、
５−シーｔｅ丁−フチルフェニル−５−クロロベンゾト
リアゾール１重量部を加え、３本ペイントロールにてよ
く混合した配合物を作製し、これを主剤とし７た。Comparative Example 1 Average molecular weight 8000, terminal group: (EH3 ((IJ(30)2Si (lJI2(J(2CI(
For 100 parts by weight of polypropylene oxide having 80% of all terminal groups, 100 parts by weight of fatty acid-treated calcium carbonate (manufactured by Shiraishi Tunorsium, trade name 0CR), 28 parts by weight of rutile titanium oxide, and epoxy hexahydrophthal. Dioctyl acid 35 parts by weight, dioctyl phthalate 20 parts by weight, hydrogenated castor oil 6 parts by weight, carphone fluff 0.5 parts by weight, oligoester acrylate-1~ (Toagosei Chemical Co., Ltd., trade name M-8060) 5 N-jobu, 2.
1 part by weight of 2-methylene-bis-(4-methyl-6-ter-butylphenol), 2(2-hydroxy-3',
1 part by weight of 5-sheet-phthylphenyl-5-chlorobenzotriazole was added and thoroughly mixed using three paint rolls to prepare a formulation, which was used as the main ingredient.
オクチル酸錫３重量部、ラウリルアミン０５重量部、ジ
オクチルフタシー１−６．５重量部、重質炭酸カルシウ
ム２０重量部、水添化ヒマシ油０．２重量部を加え、ホ
モジナイザー（日本精機製作所）で１００００回／分で
１５分間攪拌し、よく混合。Add 3 parts by weight of tin octylate, 05 parts by weight of laurylamine, 1-6.5 parts by weight of dioctyl phtathy, 20 parts by weight of heavy calcium carbonate, and 0.2 parts by weight of hydrogenated castor oil, and use a homogenizer (Nippon Seiki Seisakusho Co., Ltd.) ) for 15 minutes at 10,000 times/min to mix well.
分散した配合物を作製した。これを硬化剤とした。A dispersed formulation was made. This was used as a hardening agent.
このようにして得られた主剤と硬化剤を１０：１の重量
比で混合し、０．０７５ｍｍ厚のシートを作製し、３５
°Ｃ８０％湿度下におき、タックフリ一時間（ＪＩＳ−
Ａ ５ ７ ５ ８に従う）を測定した。The base resin and curing agent thus obtained were mixed at a weight ratio of 10:1 to prepare a sheet with a thickness of 0.075 mm.
Place at 80% humidity at °C for 1 hour without tack (JIS-
A 5 7 5 8) was measured.
比較例２
比較例１において、硬化触媒中、ラウリルアミ、／ ０
． ５ Ｍ ｔ 部の代わりにステアリルアミン１０重
量部添加すること以外は同様にして硬化シートを作製し
、タックフリ一時間を測定した。Comparative Example 2 In Comparative Example 1, in the curing catalyst, lauryl amine, / 0
．． A cured sheet was prepared in the same manner except that 10 parts by weight of stearylamine was added instead of 5 M t parts, and the tack-free time was measured.
実施例１〜４
比較例１に対し、表１に示すようなゼオライトを硬化剤
に添加する以外は同様にして硬化シートを作製し、タッ
クフリ一時間を測定した（実施例１、２，３．４）。ゼ
オライトの添加方法は、手順として■オクチル酸錫３重
量部、ラウリルアミン０．５重量部及びゼオライト２重
量部を添加し、スパチュラでよく攪拌する、■残りの添
加物を加えホモジナイザーで作製する。測定結果を表１
に記す。Examples 1 to 4 Cured sheets were prepared in the same manner as in Comparative Example 1 except that zeolite as shown in Table 1 was added to the curing agent, and the tack-free time was measured (Examples 1, 2, 3. 4). The method for adding zeolite is as follows: 1) Add 3 parts by weight of tin octylate, 0.5 parts by weight of laurylamine, and 2 parts by weight of zeolite, and stir well with a spatula; 2) Add the remaining additives and prepare with a homogenizer. Table 1 shows the measurement results.
It is written in
実施例５〜８
比較例２に対し、表１に示すようなゼオライトを硬化剤
に添加する以外は同様にして硬化ノー１〜を作製し、タ
ックフリ一時間を測定した（実施例５、６，７．８）。Examples 5 to 8 Cured No. 1 to Comparative Example 2 were prepared in the same manner except that zeolite as shown in Table 1 was added to the curing agent, and one hour of tack-free was measured (Examples 5, 6, 7.8).
ゼオライトの添加方法は実施例１〜４と同じである。The method of adding zeolite is the same as in Examples 1-4.
ｃノン６丁＃：す
実施例９〜１３
比較例１に対して、表２に示すようなケイ酸含有化合物
２重量部を硬化剤に添加する以外は同様にして硬化シー
トを作製し、タックフリ一時間を測定した（実施例９，
１０，１１，１２．１３）。c Non-6 #: Examples 9 to 13 Cured sheets were prepared in the same manner as in Comparative Example 1 except that 2 parts by weight of a silicic acid-containing compound as shown in Table 2 was added to the curing agent. One hour was measured (Example 9,
10, 11, 12.13).
ケイ酸含有化合物の添加方法は、次の手順による。The method for adding the silicic acid-containing compound is as follows.
い触媒を添加、■ケイ酸含有化合物を添加してスパチュ
ラでよく混合する、■残りの組成物を添加してホモジナ
イザーて１００００回／分で１５分間攪拌、混合する。(1) Add the silicic acid-containing compound and mix well with a spatula; (2) Add the remaining composition and mix with a homogenizer at 10,000 times/min for 15 minutes.
測定結果を表２に記す。The measurement results are shown in Table 2.
実施例１４〜１８
比較例２に対して、表２に示すようなケイ酸含有化合物
を硬化剤に添加する以外は同様にしてタックフリ一時間
を測定した（実施例１４．１５゜１６．１７．１８）。Examples 14 to 18 Tack-free one hour was measured in the same manner as in Comparative Example 2, except that the silicic acid-containing compounds shown in Table 2 were added to the curing agent (Example 14.15°16.17. 18).
作製手順は実施例９〜１３と同じである。結果を表２に
記す。The manufacturing procedure is the same as Examples 9-13. The results are shown in Table 2.
Claims (5)
基を有し、主鎖が本質的にポリエーテルである重合体１
００重量部 （ｂ） ケイ酸含有化合物００１〜３０重量部（ｃ）
硬化触媒０００１〜１０重量部を含有する室温硬化
性組成物。(1) (a) Polymer 1 having crosslinkable hydrolyzable silicone functional groups and whose main chain is essentially a polyether
00 parts by weight (b) Silicic acid-containing compound 001-30 parts by weight (c)
A room temperature curable composition containing 0001 to 10 parts by weight of a curing catalyst.
コキシシリル基である特許請求の範囲第１項記載の組成
物。(2) The composition according to claim 1, wherein the hydrolyzable silicone functional group in (a) is an alkoxysilyl group.
ンである特許請求の範囲第１項記載の組成物。(3) The composition according to claim 1, wherein the main chain of (a) is essentially polyoxypropylene.
る特許請求の範囲第１項、第２項または第３項記載の組
成物。(4) The composition according to claim 1, 2 or 3, wherein the silicic acid-containing compound (b) is a zeolite.
請求の範囲第１項、第２項、第３項または第４項記載の
組成物。(5) The composition according to claim 1, 2, 3, or 4, wherein the curing catalyst (c) is a tin-based compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22459282A JPS59113051A (en) | 1982-12-20 | 1982-12-20 | Room temperature curable composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22459282A JPS59113051A (en) | 1982-12-20 | 1982-12-20 | Room temperature curable composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59113051A true JPS59113051A (en) | 1984-06-29 |
| JPH036941B2 JPH036941B2 (en) | 1991-01-31 |
Family
ID=16816139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22459282A Granted JPS59113051A (en) | 1982-12-20 | 1982-12-20 | Room temperature curable composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59113051A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6346282A (en) * | 1987-08-07 | 1988-02-27 | Semedain Kk | Adhesive |
| EP0810301A1 (en) * | 1996-05-31 | 1997-12-03 | Toyota Jidosha Kabushiki Kaisha | Ceramic heat insulating layer and process for forming same |
| JP2005281404A (en) * | 2004-03-29 | 2005-10-13 | Aica Kogyo Co Ltd | Moisture curable resin composition and its curing acceleration method |
| JP2008111131A (en) * | 2001-05-17 | 2008-05-15 | Kaneka Corp | Curable composition having improved thin-layer curability and method for improving thin-layer curability |
| JP2008120859A (en) * | 2006-11-08 | 2008-05-29 | Toyota Motor Corp | Curing method of sealing material and assembling method of electronic equipment |
| WO2011021589A1 (en) * | 2009-08-17 | 2011-02-24 | 旭硝子株式会社 | Curable composition |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51107399A (en) * | 1975-03-14 | 1976-09-22 | Furuuitsudomasutaa Inc | |
| JPS5212218A (en) * | 1975-07-19 | 1977-01-29 | Nippon Chemical Ind | Method of manufacturing hydrated alkali silicate glass |
| JPS5273998A (en) * | 1975-12-16 | 1977-06-21 | Kanegafuchi Chem Ind Co Ltd | Room temperature curing compositions |
| JPS5556154A (en) * | 1978-10-23 | 1980-04-24 | Kanegafuchi Chem Ind Co Ltd | Clear curable composition |
| JPS57155250A (en) * | 1981-03-20 | 1982-09-25 | Kanegafuchi Chem Ind Co Ltd | Curable composition |
-
1982
- 1982-12-20 JP JP22459282A patent/JPS59113051A/en active Granted
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51107399A (en) * | 1975-03-14 | 1976-09-22 | Furuuitsudomasutaa Inc | |
| JPS5212218A (en) * | 1975-07-19 | 1977-01-29 | Nippon Chemical Ind | Method of manufacturing hydrated alkali silicate glass |
| JPS5273998A (en) * | 1975-12-16 | 1977-06-21 | Kanegafuchi Chem Ind Co Ltd | Room temperature curing compositions |
| JPS5556154A (en) * | 1978-10-23 | 1980-04-24 | Kanegafuchi Chem Ind Co Ltd | Clear curable composition |
| JPS57155250A (en) * | 1981-03-20 | 1982-09-25 | Kanegafuchi Chem Ind Co Ltd | Curable composition |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6346282A (en) * | 1987-08-07 | 1988-02-27 | Semedain Kk | Adhesive |
| JPH0347674B2 (en) * | 1987-08-07 | 1991-07-22 | Cemedine Co Ltd | |
| EP0810301A1 (en) * | 1996-05-31 | 1997-12-03 | Toyota Jidosha Kabushiki Kaisha | Ceramic heat insulating layer and process for forming same |
| JP2008111131A (en) * | 2001-05-17 | 2008-05-15 | Kaneka Corp | Curable composition having improved thin-layer curability and method for improving thin-layer curability |
| JP2005281404A (en) * | 2004-03-29 | 2005-10-13 | Aica Kogyo Co Ltd | Moisture curable resin composition and its curing acceleration method |
| JP2008120859A (en) * | 2006-11-08 | 2008-05-29 | Toyota Motor Corp | Curing method of sealing material and assembling method of electronic equipment |
| WO2011021589A1 (en) * | 2009-08-17 | 2011-02-24 | 旭硝子株式会社 | Curable composition |
| JPWO2011021589A1 (en) * | 2009-08-17 | 2013-01-24 | 旭硝子株式会社 | Curable composition |
| JP5733210B2 (en) * | 2009-08-17 | 2015-06-10 | 旭硝子株式会社 | Curable composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH036941B2 (en) | 1991-01-31 |
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