JPH0341122A - Aryl-substituted polycarbosilane and its production - Google Patents
Aryl-substituted polycarbosilane and its productionInfo
- Publication number
- JPH0341122A JPH0341122A JP1176056A JP17605689A JPH0341122A JP H0341122 A JPH0341122 A JP H0341122A JP 1176056 A JP1176056 A JP 1176056A JP 17605689 A JP17605689 A JP 17605689A JP H0341122 A JPH0341122 A JP H0341122A
- Authority
- JP
- Japan
- Prior art keywords
- aryl
- aryl group
- substituted
- substituent
- formula
- 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
- 229920003257 polycarbosilane Polymers 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 8
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 4
- IVSPVXKJEGPQJP-UHFFFAOYSA-N 2-silylethylsilane Chemical compound [SiH3]CC[SiH3] IVSPVXKJEGPQJP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 239000010703 silicon Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 abstract description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 8
- 229920000642 polymer Polymers 0.000 abstract description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000919 ceramic Substances 0.000 abstract description 2
- 230000021615 conjugation Effects 0.000 abstract description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 abstract description 2
- 229910010271 silicon carbide Inorganic materials 0.000 abstract description 2
- 229910008045 Si-Si Inorganic materials 0.000 abstract 2
- 229910006411 Si—Si Inorganic materials 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- -1 trifluoromethylphenyl Chemical group 0.000 description 9
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- CCSKNYZYRFCIPK-UHFFFAOYSA-N chloro-[2-[2-(chloromethyl)phenyl]ethyl]-dimethylsilane Chemical compound C[Si](C)(Cl)CCC1=CC=CC=C1CCl CCSKNYZYRFCIPK-UHFFFAOYSA-N 0.000 description 1
- GTXZCZRTAKZLQI-UHFFFAOYSA-N chloromethyl-[2-[chloromethyl(phenyl)silyl]ethyl]-phenylsilane Chemical compound C=1C=CC=CC=1[SiH](CCl)CC[SiH](CCl)C1=CC=CC=C1 GTXZCZRTAKZLQI-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
- Ceramic Products (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、主鎖にジシレン部とエチレン部が交互に並び
、ケイ素上にアリール基を有するポリカルボシランであ
るポリ（ジシレンーエチレン）類及びその製造方法に関
するものである。これらボリ々ａシレンーエチレン）類
は、シリコンカーバイドセラミックスの原料として用い
うる上、５ｉ−３ｉ結合部分とアリール基とのσ−π共
役により、レジスト等の光反応性ポリマーとしての用途
が期待される。Detailed Description of the Invention [Industrial Application Field] The present invention relates to poly(disilene-ethylene), which is a polycarbosilane in which disylene moieties and ethylene moieties are arranged alternately in the main chain and has an aryl group on silicon. and its manufacturing method. These polysilene-ethylene) compounds can be used as raw materials for silicon carbide ceramics, and due to the σ-π conjugation between the 5i-3i bond and the aryl group, they are expected to be used as photoreactive polymers such as resists.
従来、ケイ素原子を含むポリマーとしては各種のものが
知られているが、ケイ素上にアリール基を有するポリ（
ジシレンーエチレン）類はこれまで知られていない。Conventionally, various types of polymers containing silicon atoms have been known, but poly(
Disilene-ethylene) have not been known so far.
本発明は、ケイ素上にアリール基を有するポリ（ジシレ
ンーエチレン）類、及びその製造方法を提供することを
その課題とする。An object of the present invention is to provide poly(disilene-ethylene) having an aryl group on silicon and a method for producing the same.
［課題を解決するための手段］
本発明者らは、前記課題を達成するべく鋭意研究を重ね
た結果、ケイ素上にアリール基を有する１−へロシリル
ー２−ハロシリルエタン類を、アルカリ金属と反応させ
ることにより、ケイ素上にアリール基を有するポリ（ジ
シレンーエチレン）類が得と５到ることを見いだし、本
発明に到達した。[Means for Solving the Problems] As a result of intensive research to achieve the above-mentioned problems, the present inventors have discovered that 1-herosilyl-2-halosilylethanes having an aryl group on silicon can be combined with an alkali metal. It was discovered that poly(disilene-ethylene) having an aryl group on silicon can be obtained by the reaction, and the present invention was achieved.
本発明において提供されるポリ（ジシレンーエチレン）
類は、その主鎖が一般式
％式％（）
（式中、ｎは３以上の整数を表わす）
で表わされ、各主鎖繰返し単位内のケイ素上の置換基の
少くとも１つは置換基を有していてもよいアリール基で
あり、他は置換基を有してもよいアルキル基であるもの
である。これらアリール基を例示すればフェニル基、ト
リル基、トリフルオロメチルフェニル基、フェニルフェ
ニル基、ナフチル基等をあげることができる。また、ア
ルキル基を例示すれば、メチル基、エチル基、プロピル
基等をあげることができる。置換基としては、トリフル
オロメチル基、アルコキシ基、等が挙げられる。上記ポ
リ（ジシレンーエチレン）類を例示すれば、以下の通り
である。Poly(disylene-ethylene) provided in the present invention
%() (where n represents an integer of 3 or more), and at least one of the substituents on silicon in each main chain repeating unit is One is an aryl group which may have a substituent, and the other is an alkyl group which may have a substituent. Examples of these aryl groups include phenyl, tolyl, trifluoromethylphenyl, phenylphenyl, and naphthyl groups. Examples of alkyl groups include methyl, ethyl, and propyl groups. Examples of the substituent include a trifluoromethyl group, an alkoxy group, and the like. Examples of the above poly(disilene-ethylene) are as follows.
ポリ（トリメチルフェニルジシレンーエチレン）、ポリ
（ジメチルジフェニルジシレンーエチレン）、ポリ（ト
リメチルナフチルジシレンーエチレン）、ポリ（メチル
トリフェニルジシレンーエチレン）、ポリ（テトラフェ
ニルジシレンーエチレン）等。Poly(trimethylphenyldisilene-ethylene), poly(dimethyldiphenyldisilene-ethylene), poly(trimethylnaphthyldisilene-ethylene), poly(methyltriphenyldisilene-ethylene), poly(tetraphenyldisilene-ethylene) etc.
本発明化合物の製造方法において、原料として用いられ
るｌ−シリル−２−シリルエタン類は、一般式
％式％
（式中、Ｒ″、Ｒ″、Ｒ″、Ｒ４は置換基を有していて
もよいアリール基またはアルキル基を表わすが、Ｒ′、
Ｒ’、Ｒ”、Ｒ゛の少くとも１つは置換基を有していて
もよいアリール基であり、Ｘは塩素、臭素又はヨウ素を
表わす）
で表わされるｌ−シリル−２−シリルエタン類である。In the method for producing the compound of the present invention, l-silyl-2-silylethanes used as raw materials have the general formula Represents a good aryl group or alkyl group, but R',
At least one of R', R'', and R'' is an aryl group that may have a substituent, and X represents chlorine, bromine, or iodine. be.
これらアリール基を例示すればフェニル基、トリル基、
トリフルオロメチルフェニル基、フェニルフェニル基、
ナフチル基等があげられ、アルキル基を例示すれば、メ
チル基、エチル基、プロビルン類を例示すれば、！−（
クロロジメチルシリル）−２−（クロロメチルフェニル
シリル）エタン、１，２−ビス（クロロメチルフェニル
シリル）エタン、ｌ−（クロロジメチルシリル）−２−
（クロロメチルナフチルシリル）エタン、１−（クロロ
ジエチルシリル）−２−（クロロエチルフェニルシリル
）エタン、１−（クロロメチルフェニルシリル）−２−
（クロロジフェニルシリル）エタン、１．２−ビス（ク
ロロジフェニルシリル）エタン、１．２−ビス（ブロモ
メチルフェニルシリル）エタン、１．２−ビス（ヨード
メチルフェニルシリル）エタン等があげられる。Examples of these aryl groups include phenyl group, tolyl group,
trifluoromethylphenyl group, phenylphenyl group,
Examples include naphthyl groups, and examples of alkyl groups include methyl groups, ethyl groups, and probylene groups! −(
chlorodimethylsilyl)-2-(chloromethylphenylsilyl)ethane, 1,2-bis(chloromethylphenylsilyl)ethane, l-(chlorodimethylsilyl)-2-
(chloromethylnaphthylsilyl)ethane, 1-(chlorodiethylsilyl)-2-(chloroethylphenylsilyl)ethane, 1-(chloromethylphenylsilyl)-2-
(chlorodiphenylsilyl)ethane, 1.2-bis(chlorodiphenylsilyl)ethane, 1.2-bis(bromomethylphenylsilyl)ethane, 1.2-bis(iodomethylphenylsilyl)ethane, and the like.
本発明の製造方法において用いられるアルカリ金属とし
ては、リチウム、ナトリウム、カリウムなどを用いるこ
とができ、これらは単独でも、また、混合物または合金
として用いることもできる。As the alkali metal used in the production method of the present invention, lithium, sodium, potassium, etc. can be used, and these can be used alone or as a mixture or alloy.
その形態は、分散状または液状のものが望ましいが、反
応条件により、塊りのままでも用いつる。It is preferable that it be in the form of a dispersion or a liquid, but depending on the reaction conditions, it can also be used as a lump.
アルカリ金属と１−シリル−２−シリルエタン類とのモ
ル比は、２：ｌで十分であるがＩＯ＋１〜２二１の範囲
で、ａに選ぶことができる。The molar ratio of the alkali metal to the 1-silyl-2-silylethanes is sufficient to be 2:1, but it can be selected to be a in the range of IO+1 to 221.
本発明の製造方法は、特に溶媒を用いなくても良いが、
溶媒を用いる場合には、ハロシラン類およびアルカリ金
属と反応しないかぎり、任意のものが用いられる。これ
を例示すれば、ヘキサン、ベンゼン、トルエン、キシレ
ン、エチルベンゼンなどがあげられる。Although the production method of the present invention does not particularly require the use of a solvent,
When using a solvent, any solvent can be used as long as it does not react with the halosilanes and alkali metals. Examples of this include hexane, benzene, toluene, xylene, and ethylbenzene.
本発明の方法は、室温以上の任意の温度で行なうことが
できる。塊状のアルカリ金属を用い、室温に近い温度で
反応を行う場合には、超音波照射等により、アルカリ金
属表面を活性化することが望ましい。反応混合物からの
生成ポリマーの分離は、反応液の加水分解後、溶媒抽出
により容易に行うことができる。The method of the invention can be carried out at any temperature above room temperature. When a bulk alkali metal is used and the reaction is carried out at a temperature close to room temperature, it is desirable to activate the surface of the alkali metal by ultrasonic irradiation or the like. The produced polymer can be easily separated from the reaction mixture by solvent extraction after hydrolysis of the reaction solution.
［発明の効果］
本発明により、５ｉ−３ｉ結合と、エチレン部を交互に
有し、ケイ素上にアリール基を有するポリ（ジシレンー
エチレン）類が提供され、その工業的意義は極めて太き
い。[Effects of the Invention] The present invention provides poly(disilene-ethylene) having 5i-3i bonds and ethylene moieties alternately and having an aryl group on silicon, and its industrial significance is extremely large. .
ｍｌ二本発明を実施例により許細に説明するが、本発明
はこれら実施例に限定されるものではない。EXAMPLES The present invention will be explained in detail with reference to Examples, but the present invention is not limited to these Examples.
実施例１
１−（クロロジメチルシリル）−２−（クロロメチルフ
ェニル）エタン５ｍｍｏ ｌのトルエン（５−）溶液を
、８０℃に加熱された４０％ナトリウムディスバージョ
ン（軽油）０．８５ ｇのトルエン（ｌｏｍｆｌ）スラ
リーに滴下し、さらに１２時間、８０℃で加熱した。冷
却後、エタノール２−１さらに水１０−で分解し、トル
エンで抽出し、トルエン相を水洗した。トルエン相を濃
縮乾固後、テトラヒドロフランに溶解し、メタノールを
加えて再沈させ、淡褐色ガム状物０．３７ｇを得た。前
記のようにして得られた物質は、式、ＣＨ，Ｃ，Ｈ。Example 1 A solution of 5 mmol of 1-(chlorodimethylsilyl)-2-(chloromethylphenyl)ethane in toluene (5-) was added to 0.85 g of 40% sodium dispersion (light oil) heated to 80°C in toluene. (lomfl) was added dropwise to the slurry and heated at 80° C. for an additional 12 hours. After cooling, the mixture was decomposed with ethanol 2-1 and water 10-1, extracted with toluene, and the toluene phase was washed with water. The toluene phase was concentrated to dryness, dissolved in tetrahydrofuran, and reprecipitated by adding methanol to obtain 0.37 g of a pale brown gum-like substance. The substance obtained as described above has the formula: CH,C,H.
の繰返し構造単位を有するもので、ＧＰＣ法によるポリ
スチレン換算の分子ｉＭｗは８９０００であり、そのＩ
Ｒ及びＮＭＲスペクトル分析は以下の通りである。The molecular iMw of polystyrene equivalent by GPC method is 89,000, and its I
R and NMR spectral analysis are as follows.
［ＩＲ（ＫＢｒ）分析（波長印−°）］テＳ６０（ｍ）
、２９１０（ＶＳ）、２８５０（Ｓ）、＋４８５（ＩＲ
）、＋４６０（Ｓ）、＋４２５（Ｓ）、１４００（ｍ）
、１３７５ （ｍ）、＋２９５（ｍ）、１２４０（ｖｓ
）、＋１３０（ｖｓ）、１１００（ｖｓ）、 １０５
０（ｖｓ）、８３０（ｓ）、７７０（ｓ）、７３０（ｓ
）、６９５（ｓ）、６１０（ｓ）、４６５（ｓ）。[IR (KBr) analysis (wavelength mark -°)] TeS60 (m)
, 2910 (VS), 2850 (S), +485 (IR
), +460 (S), +425 (S), 1400 (m)
, 1375 (m), +295 (m), 1240 (vs
), +130 (vs), 1100 (vs), 105
0 (vs), 830 (s), 770 (s), 730 (s
), 695(s), 610(s), 465(s).
［ＮＭＲ（ＴＨＦ−ｄ、 ） （ｐｐｍ）分析〕０．０
９−０．１０（Ｓｊ（ＣＨ，）、、 ６Ｈ，ｍ）、０．
２１−０．３５（ＰｈＳｉＣ１（、、３Ｈ，ｌ１１）、
０．５−１．０（ＣＩ−１，ＣＨ，，４Ｈ，ｍ）、７．
２−７，６（Ｃ，Ｉ（、，５１１、ｍ）。[NMR (THF-d, ) (ppm) analysis] 0.0
9-0.10(Sj(CH,), 6H,m), 0.
21-0.35(PhSiC1(,,3H,l11),
0.5-1.0 (CI-1, CH,, 4H, m), 7.
2-7,6(C,I(,,511,m).
Claims (2)
置換基を有していてもよいアリール基またはアルキル基
であるが、少くとも１つは置換基を有していてもよいア
リール基であるポリカルボシラン類。(1) The main chain is represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. Polycarbosilanes are an aryl group or an alkyl group that may have a substituent, and at least one of them is an aryl group that may have a substituent.
していてもよいアリール基またはアルキル基を表わし、
Ｒ＾１、Ｒ＾２、Ｒ＾３、Ｒ＾４の少くとも１つは置換
基を有していてもよいアリール基であり、Ｘは塩素、臭
素又はヨウ素を表わす） で表わされる１−シリル−２−シリルエタン類を、アル
カリ金属と反応させることを特徴とする、主鎖が一般式 ▲数式、化学式、表等があります▼ （式中、ｎは３以上の整数を表わす） で表わされ、各主鎖繰返し単位内のケイ素上の置換基は
置換基を有していてもよいアリール基またはアルキル基
であるが、少くとも１つは置換基を有していてもよいア
リール基であるポリカルボシラン類の製造方法。(2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R^1, R^2, R^3, R^4 are aryl groups or alkyl groups that may have substituents Representation,
At least one of R^1, R^2, R^3, and R^4 is an aryl group that may have a substituent, and X represents chlorine, bromine, or iodine. Silyl-2-silylethanes are reacted with an alkali metal, and the main chain is represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (where n represents an integer of 3 or more). The substituents on the silicon in each main chain repeating unit are an aryl group or an alkyl group which may have a substituent, but at least one is an aryl group which may have a substituent. A method for producing certain polycarbosilanes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1176056A JPH0341122A (en) | 1989-07-07 | 1989-07-07 | Aryl-substituted polycarbosilane and its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1176056A JPH0341122A (en) | 1989-07-07 | 1989-07-07 | Aryl-substituted polycarbosilane and its production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0341122A true JPH0341122A (en) | 1991-02-21 |
| JPH0547566B2 JPH0547566B2 (en) | 1993-07-19 |
Family
ID=16006949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1176056A Granted JPH0341122A (en) | 1989-07-07 | 1989-07-07 | Aryl-substituted polycarbosilane and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0341122A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002167438A (en) * | 2000-11-29 | 2002-06-11 | Jsr Corp | Silicon polymer, film forming composition and insulating film forming material |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58153931A (en) * | 1982-03-10 | 1983-09-13 | Hitachi Ltd | Radiosensitive and photosensitive organic polymeric material |
-
1989
- 1989-07-07 JP JP1176056A patent/JPH0341122A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58153931A (en) * | 1982-03-10 | 1983-09-13 | Hitachi Ltd | Radiosensitive and photosensitive organic polymeric material |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002167438A (en) * | 2000-11-29 | 2002-06-11 | Jsr Corp | Silicon polymer, film forming composition and insulating film forming material |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0547566B2 (en) | 1993-07-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |