JPS6338381B2 - - Google Patents
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- Publication number
- JPS6338381B2 JPS6338381B2 JP55084646A JP8464680A JPS6338381B2 JP S6338381 B2 JPS6338381 B2 JP S6338381B2 JP 55084646 A JP55084646 A JP 55084646A JP 8464680 A JP8464680 A JP 8464680A JP S6338381 B2 JPS6338381 B2 JP S6338381B2
- Authority
- JP
- Japan
- Prior art keywords
- silicone resin
- hour
- film
- molecular weight
- average molecular
- 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
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- 229920002050 silicone resin Polymers 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000011342 resin composition Substances 0.000 claims description 4
- 239000005062 Polybutadiene Substances 0.000 claims description 3
- 229920002857 polybutadiene Polymers 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000010408 film Substances 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 239000010703 silicon Substances 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 6
- 238000005336 cracking Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 3
- 238000013007 heat curing Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Description
【発明の詳細な説明】
本発明はシリコーン樹脂組成物に関するもので
ある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to silicone resin compositions.
３官能有機シランの加水分解縮合反応から得ら
れるラダー状シリコーン樹脂（オルガノポリシル
セスキオキサン）は耐熱性、接着性にすぐれたも
ので、耐熱性を必要とする保護膜などに格好の材
料となるものであるが、薄膜を基板上に形成させ
加熱硬化させるまでにひび割れしたり、硬化後は
ひび割れしたりする難点があり、耐熱性があまり
おとすことなくこれを改良することが望まれてい
た。 Ladder-shaped silicone resin (organopolysilsesquioxane) obtained from the hydrolytic condensation reaction of trifunctional organic silanes has excellent heat resistance and adhesive properties, making it an ideal material for protective films that require heat resistance. However, it has the disadvantage that the thin film cracks during the process of forming it on the substrate and heating and curing it, and it also cracks after curing, and it has been desired to improve this without significantly reducing the heat resistance. .
本発明者らはかかる欠点を解決すべく鋭意研究
の結果本発明に到達した。 The present inventors have arrived at the present invention as a result of intensive research to solve these drawbacks.
即ち本発明はラダー状シリコーン樹脂の耐熱性
をあまり損なわずにその製膜性を改善しかつ加熱
硬化後のひび割れを防止する目的で、ラダー状シ
リコーン樹脂と、これと相溶する特定のポリマー
またはこれらのオリゴマーとからなることを特徴
とするシリコーン樹脂組成物を提供するものであ
る。 That is, the present invention aims to improve the film formability of the ladder silicone resin without significantly impairing its heat resistance, and to prevent cracking after heat curing. The present invention provides a silicone resin composition comprising these oligomers.
本発明で用いられるラダー状シリコーン樹脂は
下式で示される。 The ladder-like silicone resin used in the present invention is represented by the following formula.
式中ＲおよびR′はメチル基、エチル基、ｎ−
プロピル基、イソブチル基、イソアミル基などの
アルキル基；またはビニル基などのアルケニル基
を示し、ＲとR′は同一でもまた異なつていても
よい。 In the formula, R and R' are methyl group, ethyl group, n-
It represents an alkyl group such as a propyl group, an isobutyl group, an isoamyl group, or an alkenyl group such as a vinyl group, and R and R' may be the same or different.
ラダー状シリコーン樹脂の重合度ｎは10〜1000
が好ましく、また数平均分子量は5000〜100000の
ものが好ましい。 The degree of polymerization n of ladder silicone resin is 10 to 1000
is preferable, and the number average molecular weight is preferably 5,000 to 100,000.
本発明で用いられるラダー状シリコーン樹脂
は、たとえばVysokomol、Soyed、A12巻663頁
（1970年）、Izu、Akad、NaukSSSR、Ser、
Khim、625頁（1969年）、特開昭50−111197、同
50−111198、同50−111199、同50−139900、ある
いは同53−88099に提案されているような方法で
製造される。 The ladder silicone resin used in the present invention is, for example, Vysokomol, Soyed, Vol. A12, p. 663 (1970), Izu, Akad, NaukSSSR, Ser.
Khim, 625 pages (1969), Japanese Patent Publication No. 50-111197, same.
50-111198, 50-111199, 50-139900, or 53-88099.
ラダー状シリコーン樹脂に混合しうるポリマー
あるいはオリゴマーとしては、OH基をもつシリ
コーン樹脂、OH基をもつシリコーンオリゴマ
ー、ならびにポリエチレングリコール、ポリテト
ラメチレンエーテルグリコール、α、ω−ジヒド
ロキシ−ポリブタジエンおよびこれらのオリゴマ
ーから選ばれる少なくとも１種である。 Polymers or oligomers that can be mixed with the ladder silicone resin include silicone resins with OH groups, silicone oligomers with OH groups, polyethylene glycol, polytetramethylene ether glycol, α,ω-dihydroxy-polybutadiene, and oligomers thereof. At least one selected type.
ラダー状シリコーン樹脂に混合しうるポリマー
あるいはオリゴマーの好ましい数平均分子量は混
合されるポリマーあるいはオリゴマーによつて異
なるが、ほぼ500〜30000、特に1000〜20000程度
が用いられる。 The preferred number average molecular weight of the polymer or oligomer that can be mixed with the ladder-like silicone resin varies depending on the polymer or oligomer to be mixed, but it is approximately 500 to 30,000, particularly about 1,000 to 20,000.
本発明のシリコーン樹脂組成物は塗膜を形成し
た際にラダー状シリコーン樹脂と上記ポリマーあ
るいはオリゴマーとが均一に混合していさえすれ
ば、その混合方法は特に限定されないが、たとえ
ば溶液ブレンドなどで混合することができる。ラ
ダー状シリコーン樹脂に混合するポリマーあるい
はオリゴマーの量が増すにつれて得られた組成物
の耐熱性が低下するので混合する上記ポリマーあ
るいはオリゴマーの量はラダー状シリコーン樹脂
の10重量％以下が好ましい。 The method of mixing the silicone resin composition of the present invention is not particularly limited as long as the ladder silicone resin and the polymer or oligomer are mixed uniformly when forming a coating film, but for example, mixing by solution blending etc. can do. As the amount of polymer or oligomer mixed into the ladder silicone resin increases, the heat resistance of the resulting composition decreases, so the amount of the polymer or oligomer mixed is preferably 10% by weight or less of the ladder silicone resin.
上述の方法で得られた組成物は適当な溶媒に溶
かして基板状に塗布し薄膜を形成させることがで
きる。塗布方法には例えばスプレー塗布、スピン
ナー塗布など通常用いられている方法が適用でき
る。かかる方法で得られた薄膜は加熱硬化前に溶
剤が揮散した状態でも加熱硬化後でもあるいは硬
化後400〜500℃の熱処理をしてもひび割れはおこ
らず耐熱性保護膜、耐熱性絶縁膜として特に電子
材料分野で応用範囲の広いものである。 The composition obtained by the above method can be dissolved in a suitable solvent and applied to a substrate to form a thin film. As the coating method, commonly used methods such as spray coating and spinner coating can be applied. The thin film obtained by this method does not crack even when the solvent is volatilized before heat curing, after heat curing, or after heat treatment at 400 to 500°C, making it particularly useful as a heat-resistant protective film or a heat-resistant insulating film. It has a wide range of applications in the field of electronic materials.
以下に実施例を記す。 Examples are described below.
実施例 １
数平均分子量約30000のメチルポリシルセスキ
オキサン２ｇおよび数平均分子量15000のα，ω
−ジヒドロキシジメチルポリシロキサン0.1ｇを
トルエン15mlに溶解する。これを1500rpmでシリ
コンウエハー上にスピンナー塗布する。その後80
℃で１時間予備加熱したのち、250℃で２時間加
熱硬化させて厚さ2μｍの膜を得た。この薄膜は
450℃で１時間熱処理した後、室温に放置しても
ひび割れはおこらなかつた。Example 1 2 g of methylpolysilsesquioxane with a number average molecular weight of about 30,000 and α, ω with a number average molecular weight of 15,000
-Dissolve 0.1 g of dihydroxydimethylpolysiloxane in 15 ml of toluene. This is applied onto a silicon wafer using a spinner at 1500 rpm. then 80
After preheating at ℃ for 1 hour, the mixture was heated and cured at 250 ℃ for 2 hours to obtain a film with a thickness of 2 μm. This thin film
After heat treatment at 450°C for 1 hour, no cracking occurred even when left at room temperature.
実施例 ２
数平均分子量約20000のメチルポリシルセスキ
オキサン２ｇに日本ポリウレタン社製のポリテト
ラメチレンエーテルグリコール（PTG−400、数
平均分子量1500）0.1ｇをトルエン15mlに溶解す
る。これを1500rpmでシリコンウエハー上にスピ
ンナー塗布し80℃で１時間予備加熱したのち、
250℃で２時間加熱硬化させ厚さ1.5μｍの膜を得
た。このものはさらに450℃で１時間熱処理した
のち、室温に放置してもひび割れは認められなか
つた。Example 2 In 2 g of methylpolysilsesquioxane having a number average molecular weight of about 20,000, 0.1 g of polytetramethylene ether glycol (PTG-400, number average molecular weight 1,500) manufactured by Nippon Polyurethane Co., Ltd. is dissolved in 15 ml of toluene. This was applied onto a silicon wafer using a spinner at 1500 rpm and preheated at 80°C for 1 hour.
The film was cured by heating at 250°C for 2 hours to obtain a film with a thickness of 1.5 μm. After this product was further heat treated at 450°C for 1 hour, no cracks were observed even when it was left at room temperature.
実施例 ３
数平均分子量約20000のメチルポリシルセスキ
オキサン２ｇに和光純薬製のポリエチレングリコ
ール−2000（数平均分子量2000）0.09ｇをトルエ
ン15mlに溶解する。これを1500rpmでシリコンウ
エハー上にスピンナー塗布し80℃で１時間予備加
熱し、250℃で２時間加熱硬化して厚さ2μｍの膜
を得た。この膜はさらに450℃で１時間熱処理し
た後、室温に放置してもひび割れは認められなか
つた。Example 3 In 2 g of methylpolysilsesquioxane having a number average molecular weight of about 20,000, 0.09 g of polyethylene glycol-2000 (number average molecular weight 2000) manufactured by Wako Pure Chemical Industries, Ltd. is dissolved in 15 ml of toluene. This was spin-coated onto a silicon wafer at 1500 rpm, preheated at 80°C for 1 hour, and heated and cured at 250°C for 2 hours to obtain a 2 μm thick film. After this film was further heat treated at 450°C for 1 hour, no cracks were observed even when it was left at room temperature.
実施例 ４
ビニルトリエトキシシランとフエニルトリエト
キシシランの共加水分解縮合で得られる数平均分
子量10000のポリシルセスキオキサン３ｇおよび
数平均分子量15000のα，ω−ジヒドロキシジメ
チルポリシロキサン0.1ｇをトルエン15mlに溶解
する。これを2000rpmでシリコンウエハー上にス
ピンナー塗布し、80℃で１時間予備加熱したのち
250℃で２時間加熱硬化させ、厚さ2μｍの膜を得
た。このものはさらに１時間熱処理したのち室温
に放置してもひび割れは認められなかつた。Example 4 3 g of polysilsesquioxane with a number average molecular weight of 10,000 obtained by cohydrolytic condensation of vinyltriethoxysilane and phenyltriethoxysilane and 0.1 g of α,ω-dihydroxydimethylpolysiloxane with a number average molecular weight of 15,000 were added to toluene. Dissolve in 15ml. This was applied with a spinner at 2000 rpm onto a silicon wafer, and after preheating at 80℃ for 1 hour,
It was heated and cured at 250°C for 2 hours to obtain a film with a thickness of 2 μm. No cracks were observed in this product even after it was further heat treated for 1 hour and then left at room temperature.
比較例 １
数平均分子量30000のメチルポリシルセスキオ
キサン２ｇを15mlのトルエンに溶解する。これを
1500rpmでガラス基板上にスピンナー塗布し、80
℃で１時間予備加熱したのち、250℃で２時間加
熱硬化させ厚さ2μｍの膜を得た。このものをさ
らに450℃で１時間熱処理したのち室温で放冷し
たところ細かいひび割れが認められた。Comparative Example 1 2 g of methylpolysilsesquioxane having a number average molecular weight of 30,000 is dissolved in 15 ml of toluene. this
Spinner coated on glass substrate at 1500 rpm, 80
After preheating for 1 hour at 250°C, the mixture was cured by heating at 250°C for 2 hours to obtain a film with a thickness of 2 μm. When this material was further heat treated at 450°C for 1 hour and then allowed to cool at room temperature, fine cracks were observed.
実施例 ５
数平均分子量約5000のメチルポリシルセスキオ
キサン２ｇおよび数平均分子量1500のα，ω−ジ
ヒドロキシジメチルポリシロキサン0.2ｇをトル
エン10mlに溶解し、これを1500rpmでシリコンウ
エハー上にスピンナーで塗布した。その後、200
℃で１時間加熱硬化させ、厚さ2μｍの膜を得た。
この薄膜は、450℃で１時間熱処理したのち、室
温で放置してもひび割れは起こらなかつた。Example 5 2 g of methylpolysilsesquioxane with a number average molecular weight of about 5000 and 0.2 g of α,ω-dihydroxydimethylpolysiloxane with a number average molecular weight of 1500 were dissolved in 10 ml of toluene, and this was coated on a silicon wafer with a spinner at 1500 rpm. did. then 200
It was heated and cured at ℃ for 1 hour to obtain a film with a thickness of 2 μm.
This thin film did not crack even after being heat treated at 450°C for 1 hour and then left at room temperature.
実施例 ６
数平均分子量約5000のメチルポリシルセスキオ
キサン２ｇおよびOH基をもつシリコーン樹脂
（TSR160、東芝シリコーン(株)製）0.2ｇをトルエ
ン10mlに溶解し、これを1500rpmでシリコンウエ
ハー上にスピンナーで塗布した。その後、80℃で
30分、予備加熱したのち、200℃で１時間加熱硬
化させ、厚さ2.5μｍの膜を得た。この薄膜は、
450℃で１時間熱処理したのち、室温で放置して
もひび割れは起こらなかつた。Example 6 2 g of methylpolysilsesquioxane with a number average molecular weight of about 5000 and 0.2 g of a silicone resin with an OH group (TSR160, manufactured by Toshiba Silicone Co., Ltd.) were dissolved in 10 ml of toluene, and this was spread on a silicon wafer at 1500 rpm. Applied with a spinner. Then at 80℃
After preheating for 30 minutes, the mixture was cured by heating at 200° C. for 1 hour to obtain a film with a thickness of 2.5 μm. This thin film is
After heat treatment at 450°C for 1 hour, no cracking occurred even when left at room temperature.
実施例 ７
数平均分子量約5000のビニルポリシルセスキオ
キサン２ｇおよび数平均分子量1500のα，ω−ジ
ヒドロキシジメチルポリシロキサン0.2ｇをトル
エン10mlに溶解する。Example 7 2 g of vinyl polysilsesquioxane having a number average molecular weight of about 5000 and 0.2 g of α,ω-dihydroxydimethylpolysiloxane having a number average molecular weight of 1500 are dissolved in 10 ml of toluene.
これを1500rpmでシリコンウエハー上にスピン
ナー塗布する。その後、200℃で１時間加熱硬化
させて厚さ2.5μｍの膜を得た。 This is applied onto a silicon wafer using a spinner at 1500 rpm. Thereafter, the film was cured by heating at 200° C. for 1 hour to obtain a film with a thickness of 2.5 μm.
この薄膜は、450℃で１時間熱処理したのち、
室温に放置してもひび割れは起こらなかつた。 After heat-treating this thin film at 450℃ for 1 hour,
No cracking occurred even when left at room temperature.
実施例 ８
数平均分子量約5000のメチルポリシルセスキオ
キサン２ｇおよび数平均分子量2700のα，ω−ジ
ヒドロキシ−１，４−ポリブタジエン（アルコ
ケミカル社製、POLY BD）0.2ｇをトルエン10
mlに溶解する。Example 8 2 g of methylpolysilsesquioxane with a number average molecular weight of about 5000 and α,ω-dihydroxy-1,4-polybutadiene (alcohol) with a number average molecular weight of 2700
Chemical Co., Ltd., POLY BD) 0.2g to toluene 10
Dissolve in ml.
これを1500rpmでシリコンウエハー上にスピン
ナー塗布する。その後、200℃で１時間加熱硬化
させて厚さ2.0μｍの膜を得た。 This is applied onto a silicon wafer using a spinner at 1500 rpm. Thereafter, the film was cured by heating at 200° C. for 1 hour to obtain a film with a thickness of 2.0 μm.
この薄膜は、450℃で１時間熱処理したのち、
室温に放置してもひび割れは起こらなかつた。 After heat-treating this thin film at 450℃ for 1 hour,
No cracking occurred even when left at room temperature.
Claims (1)
ケニル基を示す）、これと相溶するOH基をもつ
シリコーン樹脂、OH基をもつシリコーンオリゴ
マー、ならびにポリエチレングリコール、ポリテ
トラメチレンエーテルグリコール、α，ω−ジヒ
ドロキシ−ポリブタジエンおよびこれらのオリゴ
マーから選ばれる少なくとも１種とからなること
を特徴とするシリコーン樹脂組成物。[Claims] 1. Ladder-shaped silicone resin represented by the following formula and (In the formula, R and R' represent an alkyl group or an alkenyl group), a silicone resin having an OH group that is compatible with this, a silicone oligomer having an OH group, and polyethylene glycol, polytetramethylene ether glycol, α, A silicone resin composition comprising at least one selected from ω-dihydroxy-polybutadiene and oligomers thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8464680A JPS5710643A (en) | 1980-06-24 | 1980-06-24 | Silicone resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8464680A JPS5710643A (en) | 1980-06-24 | 1980-06-24 | Silicone resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5710643A JPS5710643A (en) | 1982-01-20 |
| JPS6338381B2 true JPS6338381B2 (en) | 1988-07-29 |
Family
ID=13836455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8464680A Granted JPS5710643A (en) | 1980-06-24 | 1980-06-24 | Silicone resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5710643A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS613120A (en) * | 1984-06-15 | 1986-01-09 | Dainippon Ink & Chem Inc | Device for color liquid crystal display |
| JPS613124A (en) * | 1984-06-15 | 1986-01-09 | Dainippon Ink & Chem Inc | Color liquid crystal display device |
| JP2649157B2 (en) * | 1987-03-10 | 1997-09-03 | 三菱電機株式会社 | Semiconductor device |
| JP2011202001A (en) * | 2010-03-25 | 2011-10-13 | Honda Motor Co Ltd | Siloxane-based coating composition, and method for coating by using the same |
| JP2019119804A (en) * | 2018-01-05 | 2019-07-22 | スリーエム イノベイティブ プロパティズ カンパニー | Curable composition and optical member |
| WO2023218889A1 (en) * | 2022-05-13 | 2023-11-16 | Ａｇｃ株式会社 | Composition, compound, surface treatment agent, article and method for producing article |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49132141A (en) * | 1973-04-16 | 1974-12-18 |
-
1980
- 1980-06-24 JP JP8464680A patent/JPS5710643A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49132141A (en) * | 1973-04-16 | 1974-12-18 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5710643A (en) | 1982-01-20 |
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