JPH0737510B2 - Dispersion stabilizer for silicone resin particles - Google Patents
Dispersion stabilizer for silicone resin particlesInfo
- Publication number
- JPH0737510B2 JPH0737510B2 JP63171446A JP17144688A JPH0737510B2 JP H0737510 B2 JPH0737510 B2 JP H0737510B2 JP 63171446 A JP63171446 A JP 63171446A JP 17144688 A JP17144688 A JP 17144688A JP H0737510 B2 JPH0737510 B2 JP H0737510B2
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- resin particles
- silicone
- silicone resin
- dispersion stabilizer
- 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.)
- Expired - Lifetime
Links
- 239000002245 particle Substances 0.000 title claims description 12
- 229920002050 silicone resin Polymers 0.000 title claims description 10
- 239000006185 dispersion Substances 0.000 title claims description 5
- 239000003381 stabilizer Substances 0.000 title claims description 5
- 229920001296 polysiloxane Polymers 0.000 claims description 29
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 9
- -1 polysiloxane Polymers 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005650 substituted phenylene group Chemical group 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 description 22
- 229920000647 polyepoxide Polymers 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000007259 addition reaction Methods 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UALAKBZSBJIXBP-UHFFFAOYSA-N 1-phenylethane-1,1,2,2-tetrol Chemical compound OC(O)C(O)(O)C1=CC=CC=C1 UALAKBZSBJIXBP-UHFFFAOYSA-N 0.000 description 1
- WGFZZGXKRATULP-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)aniline Chemical compound NC1=CC=CC=C1OCC1OC1 WGFZZGXKRATULP-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Silicon Polymers (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明はシリコーン樹脂粒子の分散安定剤、更に詳しく
は、オルガノポリシロキサンとグリシジル基含有化合物
との付加反応生成物であるポリシロキサン変性体から成
る、エポキシ樹脂マトリックス中にシリコーン樹脂粒子
を安定分散させるのに有用なシリコーン樹脂粒子の分散
安定剤に関する。TECHNICAL FIELD The present invention relates to a dispersion stabilizer for silicone resin particles, more specifically, a polysiloxane modified product which is an addition reaction product of an organopolysiloxane and a glycidyl group-containing compound. The present invention relates to a dispersion stabilizer for silicone resin particles, which is useful for stably dispersing silicone resin particles in an epoxy resin matrix.
従来技術と発明の解決すべき課題 従来より、エポキシ樹脂は一般に耐クラツク性や靭性に
欠け、さらに硬化時の収縮によるストレスの緩和が困難
とされており、このためエポキシ樹脂マトリツクス中に
シリコーン樹脂粒子を配合してその改質を行う方法が採
られている。しかし、経時変化によつてマトリツクス中
でシリコーン樹脂粒子の粒径が増大したり、あるいは特
に高温条件下での硬化時に粒径が大きく変動するといつ
た問題があつた。Conventional Technology and Problems to be Solved by the Invention Conventionally, epoxy resins are generally lacking in crack resistance and toughness, and it has been difficult to alleviate stress due to shrinkage during curing. Therefore, epoxy resin matrix contains silicone resin particles. Is used to modify the composition. However, there has been a problem that the particle size of the silicone resin particles in the matrix increases due to aging, or the particle size fluctuates greatly during curing particularly under high temperature conditions.
本発明は、かかるシリコーン樹脂粒子の安定分散剤の提
供を目的とする。The present invention aims to provide a stable dispersant for such silicone resin particles.
発明の構成と効果 すなわち、本発明に係るシリコーン樹脂粒子の分散安定
剤は、式： 〔式中、X1はCH3、−Ｒ′−NH2、−Ｒ′−NH−Ｒ″−NH
2、−Ｒ′−COOHまたは−OR（Ｒ′は−OC2H4−、炭素
数１〜20のアルキレン基、フェニレン基または置換フェ
ニレン基、Ｒ″は炭素数１〜20のアルキレン基、および
ＲはCH3またはC2H5）、X2はCH3、−Ｒ′−NH2、−
Ｒ′−NH−Ｒ″−NH2、−Ｒ′−SHまたは−Ｒ′−COOH
（Ｒ′およびＲ″は前記と同意義）であって、X1とX2が
共にCH3である場合を除く、ａは１〜1000、およびｂは
１〜100である〕のオルガノポリシロキサンと、分子中
に少なくとも１個のグリシジル基を有する化合物（以
下、グリシジル基含有化合物という）をを付加反応して
得られるポリシロキサン変性体から成る。Structure and Effect of the Invention That is, the dispersion stabilizer for silicone resin particles according to the present invention has the formula: [In the formula, X 1 is CH 3 , -R'-NH 2 , -R'-NH-R "-NH.
2 , —R′—COOH or —OR (R ′ is —OC 2 H 4 —, an alkylene group having 1 to 20 carbon atoms, a phenylene group or a substituted phenylene group, R ″ is an alkylene group having 1 to 20 carbon atoms, and R is CH 3 or C 2 H 5), X 2 is CH 3, -R'-NH 2, -
R'-NH-R "-NH 2 , -R'-SH or -R'-COOH
(Wherein R ′ and R ″ have the same meanings as defined above) and a is 1 to 1000 and b is 1 to 100, except when X 1 and X 2 are both CH 3. And a polysiloxane modified product obtained by an addition reaction of a compound having at least one glycidyl group in the molecule (hereinafter referred to as a glycidyl group-containing compound).
本発明のポリシロキサン変性体は、上記オルガノポリシ
ロキサン〔Ｉ〕とグリシジル基含有化合物を付加反応さ
せることにより製造することができる。The modified polysiloxane of the present invention can be produced by subjecting the above organopolysiloxane [I] and a glycidyl group-containing compound to an addition reaction.
上記オルガノポリシロキサン〔Ｉ〕は、具体的には、両
末端アミノ変性シリコーンとしてチツソ（株）製の「FM
3311」、「FM3321」、「FM3325」（X1＝−C3H6−N
H2）、トーレ・シリコーン（株）製の「BX16−853」、
「BX16−853B」（X1＝−Ｒ′−NH2）、信越化学（株）
製の「Ｘ−22−161AS」、「Ｘ−22−161A」、「Ｘ−22
−161B」、「Ｘ−22−161C」（X1＝−C3H6−NH2）、PET
RACH SYSTEMS社製の「PS510」、「PS513」等、側鎖ア
ミノ変性シリコーン（X1＝CH3、X2＝−Ｒ′−NH2、−
Ｒ′−NH−Ｒ″−NH2）としてトーレ・シリコーン
（株）製の「SF8417」、「BY16−828」、「BX16−85
9」、信越化学（株）製の「KF−393」、「KF−859」、
「KF−860」、「KF−861」、「KF−867」、「Ｘ−22−3
80D」、「KF−864」、「KF−865」、「Ｘ−22−368
0」、「Ｘ−22−3801C」等、側鎖カルボキシ変性シリコ
ーンとしてトーレ・シリコーン（株）製の「SF−841
8」、信越化学（株）製の「Ｘ−22−3701E」、「Ｘ−22
−3710」、「Ｘ−22−3715」等、末端カルボキシ変性シ
リコーンとしてPETRACH、SYSTEMS社製の「PS563」等、
側鎖メルカプト変性シリコーンとしてトーレ・シリコー
ン（株）製の「BX16−838A」、「BY16−838」、信越化
学（株）製の「Ｘ−22−980」等が挙げられる。The above-mentioned organopolysiloxane [I] is specifically, as an amino-modified silicone at both ends, "FM" manufactured by Chitso Corporation.
3311 "," FM3321 "," FM3325 "(X 1 = -C 3 H 6 -N
H 2 ), "BX16-853" manufactured by Torre Silicone Co., Ltd.,
"BX16-853B" (X 1 = -R'-NH 2 ), Shin-Etsu Chemical Co.,
"X-22-161AS", "X-22-161A", "X-22"
-161B "," X-22-161C "(X 1 = -C 3 H 6 -NH 2), PET
RACH SYSTEMS manufactured by "PS510", "PS513", etc., the side chain amino-modified silicone (X 1 = CH 3, X 2 = -R'-NH 2, -
R'-NH-R "-NH 2 ) as Toray Silicone Co., Ltd." SF8417 "," BY16-828 "," BX16-85
9 ", Shin-Etsu Chemical Co., Ltd." KF-393 "," KF-859 ",
"KF-860", "KF-861", "KF-867", "X-22-3"
80D "," KF-864 "," KF-865 "," X-22-368 "
0 "," X-22-3801C "and the like, as side chain carboxy-modified silicone," SF-841 "manufactured by Toray Silicone Co., Ltd.
8 "," X-22-3701E "manufactured by Shin-Etsu Chemical Co., Ltd.," X-22 "
-3710 "," X-22-3715 ", etc., PETRACH as terminal carboxy-modified silicone," PS563 "manufactured by SYSTEMS, etc.,
Examples of the side chain mercapto-modified silicone include "BX16-838A" and "BY16-838" manufactured by Toray Silicone Co., Ltd. and "X-22-980" manufactured by Shin-Etsu Chemical Co., Ltd.
上記グリシジル基含有化合物としては、通常のエポキシ
樹脂、たとえばグリシジルアミン型エポキシ樹脂（N,N,
N′,N′−テトラグリシジルアミノジフエニルメタン、
N,N−ジクリシジルメタン（またはパラ）アミノフエノ
ールグリシジルエーテルおよびそれらの縮合物）、ノボ
ラツク型エポキシ樹脂（フエノールノボラツク型、クレ
ゾールノボラツク型）、ビスフエノールＡ型エポキシ樹
脂、ウレタン変性ビスフエノールＡ型エポキシ樹脂、臭
素化ビスフエノールＡ型エポキシ樹脂、脂環式エポキシ
樹脂、ビスフエノールＦ型エポキシ樹脂、レゾルシン型
エポキシ樹脂、テトラヒドロキシフエニルエタン型エポ
キシ樹脂、ポリアルコール型エポキシ樹脂、ポリグリコ
ール型エポキシ樹脂、グリセリントリエーテル型エポキ
シ樹脂、ポリオレフイン型エポキシ樹脂、エポキシ化大
豆油、エステル型エポキシ樹脂等、その他グリシジル基
を有するブタジエンゴム、イソプレンゴムまたはアクリ
ル樹脂などが挙げられる。As the glycidyl group-containing compound, a usual epoxy resin, for example, a glycidyl amine type epoxy resin (N, N,
N ', N'-tetraglycidylaminodiphenylmethane,
N, N-diglycidyl methane (or para) aminophenol glycidyl ether and their condensates), novolak type epoxy resin (phenol novolak type, cresol novolak type), bisphenol A type epoxy resin, urethane modified bisphenol A Type epoxy resin, brominated bisphenol A type epoxy resin, alicyclic epoxy resin, bisphenol F type epoxy resin, resorcin type epoxy resin, tetrahydroxyphenylethane type epoxy resin, polyalcohol type epoxy resin, polyglycol type epoxy resin Resin, glycerin triether type epoxy resin, polyolefin type epoxy resin, epoxidized soybean oil, ester type epoxy resin and the like, and other butadiene rubber having a glycidyl group, isoprene rubber, acrylic resin and the like. That.
この付加反応は、オルガノポリシロキサン〔Ｉ〕の反応
性官能基に対して、グリシジル基含有化合物のグリシジ
ル基が過剰量となるような割合で、通常、常温乃至加熱
下（40〜150℃）で行えばよく、また必要に応じて適当
な有機溶媒（テトラヒドロフラン、トルオール、キシロ
ール、ｎ−ヘキサン、シクロヘキサン、クロロホルム、
ベンゼン、アセトン、エタノール、メタノールなど）の
単独あるいは混合物中で行つてもよい。This addition reaction is carried out at a ratio such that the glycidyl group of the glycidyl group-containing compound is in excess with respect to the reactive functional group of the organopolysiloxane [I], usually at room temperature or under heating (40 to 150 ° C.). It may be carried out, and if necessary, a suitable organic solvent (tetrahydrofuran, toluene, xylol, n-hexane, cyclohexane, chloroform,
Benzene, acetone, ethanol, methanol, etc.) alone or in a mixture.
このようにして得られるポリシロキサン変性体は、溶媒
除去後、固形乃至液状で、無色透明もしくは淡黄色乃至
白色を呈したもので、特にエポキシ樹脂マトリツクスへ
のシリコーン樹脂粒子の均一安定分散剤として有用であ
る。The modified polysiloxane thus obtained is solid or liquid and has colorless and transparent or pale yellow to white after removing the solvent, and is particularly useful as a uniform and stable dispersant for silicone resin particles in epoxy resin matrix. Is.
次に実施例を挙げて本発明をより具体的に説明する。Next, the present invention will be described more specifically with reference to examples.
実施例１ オルガノポリシロキサン〔Ｉ〕としてアミノ変性シリコ
ーン（トーレ・シリコーン（株）製、SF8417）100部
（重量部、以下同様）を、テトラヒドロフラン（THF）
に溶解（30重量％に）したビスフエノールＡ型エポキシ
樹脂（油化シエル社製、エピコート1002）溶液1670部を
50℃、36時間付加反応して、ポリシロキサン変性体を得
る。なお、反応終了をGPにより確認した。溶媒除去後白
色固形となり、融点は95℃を示した。Example 1 100 parts (parts by weight, the same applies hereinafter) of amino-modified silicone (SF8417 manufactured by Toray Silicone Co., Ltd.) as organopolysiloxane [I] was mixed with tetrahydrofuran (THF).
1670 parts of a solution of bisphenol A type epoxy resin (Epicoat 1002, manufactured by Yuka Shell Co., Ltd.) dissolved in 30% by weight of
Addition reaction is carried out at 50 ° C. for 36 hours to obtain a modified polysiloxane. The completion of the reaction was confirmed by GP. After removing the solvent, it became a white solid and had a melting point of 95 ° C.
実施例２ オルガノポリシロキサン〔Ｉ〕として両末端アミノ変性
シリコーン（チツソ社製、FM3321）100部と、ダイマー
酸変性エポキシ樹脂（油化シエル社製、エピコート87
1）の30重量％THF溶液170部を50℃、36時間付加反応し
てポリシロキサン変性体を得る。GPCにより反応終了を
確認した。淡黄色液体であり、Mn7000〜28000であつ
た。Example 2 100 parts of both-end amino-modified silicone (manufactured by Chitso Co., FM3321) as organopolysiloxane [I], and dimer acid-modified epoxy resin (manufactured by Yuka Shell Co., Epicoat 87)
170 parts of 30% by weight THF solution of 1) is subjected to addition reaction at 50 ° C for 36 hours to obtain a modified polysiloxane. The completion of the reaction was confirmed by GPC. It was a pale yellow liquid and had a Mn of 7,000 to 28,000.
実施例３ オルガノポリシロキサン〔Ｉ〕としてカルボキシ変性シ
リコーン（信越シリコーン社製、Ｘ−22−3710）100部
と、エポキシ樹脂（油化シエル社製、エピコート828）3
0重量％THF溶液900部を120℃、６時間付加反応してポリ
シロキサン変性体を得る。無色透明体であつた。Example 3 100 parts of a carboxy-modified silicone (X-22-3710 manufactured by Shin-Etsu Silicone Co., Ltd.) as an organopolysiloxane [I] and an epoxy resin (Epicoat 828 manufactured by Yuka Shell Co., Ltd.) 3
900 parts of 0 wt% THF solution is added and reacted at 120 ° C. for 6 hours to obtain a modified polysiloxane. It was a colorless transparent body.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭62−254453（ＪＰ，Ａ) 特開 昭62−260817（ＪＰ，Ａ) 特開 昭63−17927（ＪＰ，Ａ) 特開 昭63−17928（ＪＰ，Ａ) 特開 昭63−77921（ＪＰ，Ａ) 特開 昭64−22916（ＪＰ，Ａ) 特開 昭64−20226（ＪＰ，Ａ) ─────────────────────────────────────────────────── --- Continuation of the front page (56) References JP-A-62-254453 (JP, A) JP-A-62-260817 (JP, A) JP-A-63-17927 (JP, A) JP-A-63- 17928 (JP, A) JP 63-77921 (JP, A) JP 64-22916 (JP, A) JP 64-20226 (JP, A)
Claims (1)
2、−Ｒ′−COOHまたは−OR（Ｒ′は−OC2H4−、炭素
数１〜20のアルキレン基、フェニレン基または置換フェ
ニレン基、Ｒ″は炭素数１〜20のアルキレン基、および
ＲはCH3またはC2H5）、X2はCH3、−Ｒ′−NH2、−
Ｒ′−NH−Ｒ″−NH2、−Ｒ′−SHまたは−Ｒ′−COOH
（Ｒ′およびＲ″は前記と同意義）であって、X1とX2が
共にCH3である場合を除く、ａは１〜1000、およびｂは
１〜100である］ のオルガノポリシロキサンと、分子中に少なくとも１個
のグリシジル基を有する化合物とを付加反応して得られ
るポリシロキサン変性体から成ることを特徴とするシリ
コーン樹脂粒子の分散安定剤。1. A formula: [Wherein, X 1 is CH 3 , -R'-NH 2 , -R'-NH-R "-NH
2 , —R′—COOH or —OR (R ′ is —OC 2 H 4 —, an alkylene group having 1 to 20 carbon atoms, a phenylene group or a substituted phenylene group, R ″ is an alkylene group having 1 to 20 carbon atoms, and R is CH 3 or C 2 H 5), X 2 is CH 3, -R'-NH 2, -
R'-NH-R "-NH 2 , -R'-SH or -R'-COOH
(Wherein R ′ and R ″ have the same meanings as defined above), except when X 1 and X 2 are both CH 3 , a is 1 to 1000, and b is 1 to 100]. A dispersion stabilizer for silicone resin particles, which comprises a modified polysiloxane obtained by addition-reacting a compound having at least one glycidyl group in the molecule.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63171446A JPH0737510B2 (en) | 1988-07-09 | 1988-07-09 | Dispersion stabilizer for silicone resin particles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63171446A JPH0737510B2 (en) | 1988-07-09 | 1988-07-09 | Dispersion stabilizer for silicone resin particles |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63097691A Division JPH0725866B2 (en) | 1988-04-19 | 1988-04-19 | Epoxy resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01268721A JPH01268721A (en) | 1989-10-26 |
| JPH0737510B2 true JPH0737510B2 (en) | 1995-04-26 |
Family
ID=15923260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63171446A Expired - Lifetime JPH0737510B2 (en) | 1988-07-09 | 1988-07-09 | Dispersion stabilizer for silicone resin particles |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0737510B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3147677B2 (en) * | 1994-09-30 | 2001-03-19 | 株式会社村田製作所 | Liquid epoxy resin composition |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62254453A (en) * | 1986-04-25 | 1987-11-06 | Nitto Electric Ind Co Ltd | Semiconductor device |
| JPS62260817A (en) * | 1986-05-08 | 1987-11-13 | Sumitomo Bakelite Co Ltd | Epoxy resin composition and sealed semiconductor device |
| JPS6317927A (en) * | 1986-07-09 | 1988-01-25 | Sumitomo Bakelite Co Ltd | Epoxy resin composition |
| JPS6317928A (en) * | 1986-07-10 | 1988-01-25 | Sumitomo Bakelite Co Ltd | Epoxy resin composition |
| JPS6377921A (en) * | 1986-09-22 | 1988-04-08 | Nippon Kayaku Co Ltd | Aminosilane-modified epoxy resin and formation of thin film |
| JPS6420226A (en) * | 1987-07-15 | 1989-01-24 | Sumitomo Chemical Co | Production of modified epoxy resin |
| JPS6422916A (en) * | 1987-07-16 | 1989-01-25 | Sumitomo Chemical Co | Production of modified epoxy polymer |
-
1988
- 1988-07-09 JP JP63171446A patent/JPH0737510B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01268721A (en) | 1989-10-26 |
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