JPH0562615B2 - - Google Patents
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- Publication number
- JPH0562615B2 JPH0562615B2 JP60174273A JP17427385A JPH0562615B2 JP H0562615 B2 JPH0562615 B2 JP H0562615B2 JP 60174273 A JP60174273 A JP 60174273A JP 17427385 A JP17427385 A JP 17427385A JP H0562615 B2 JPH0562615 B2 JP H0562615B2
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- present
- added
- general formula
- benzene
- 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 - Fee Related
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- 229920000642 polymer Polymers 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229920001002 functional polymer Polymers 0.000 description 3
- 239000011810 insulating material Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- MVLGANVFCMOJHR-UHFFFAOYSA-N 1,4-diethynylbenzene Chemical compound C#CC1=CC=C(C#C)C=C1 MVLGANVFCMOJHR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910008045 Si-Si Inorganic materials 0.000 description 1
- 229910006411 Si—Si Inorganic materials 0.000 description 1
- JETSKDPKURDVNI-UHFFFAOYSA-N [C].[Ca] Chemical compound [C].[Ca] JETSKDPKURDVNI-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SHNKFHWZADNPMU-UHFFFAOYSA-N chloro-(chloro-ethyl-methylsilyl)-ethyl-methylsilane Chemical compound CC[Si](C)(Cl)[Si](C)(Cl)CC SHNKFHWZADNPMU-UHFFFAOYSA-N 0.000 description 1
- HHRQHEVSQICRND-UHFFFAOYSA-N chloro-(chloro-methyl-phenylsilyl)-methyl-phenylsilane Chemical compound C=1C=CC=CC=1[Si](C)(Cl)[Si](Cl)(C)C1=CC=CC=C1 HHRQHEVSQICRND-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0754—Non-macromolecular compounds containing silicon-to-silicon bonds
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Silicon Polymers (AREA)
- Organic Insulating Materials (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Description
【発明の詳細な説明】
〔発明の利用分野〕
本発明は、機能性高分子として極めて有用な新
規な重合体に関する。更に詳しくは、下記一般式
(1)で表わされる繰り返し単位よりなり、重量平均
分子量が1000〜1000000である新規な重合体に関
する。
（但し、一般式(1)中Ｒはエチル基あるいはフエ
ニル基を表わす。）
〔発明の背景〕
高分子主鎖にSi−Si結合と２価の有機基を有す
る重合体は、感光性材料や絶縁材料として極めて
有用な材料である。
この種の重合体としてはジヤーナル・オブ・ポ
リマー・サイエンス、ポリマー・レター・エデイ
シヨン（J.Polymer Sci.、Polymer Lett.Ed.）
22、669〜671（1984）に下記式(2)で表わされる繰
り返し単位よりなる重合体などが示されている
が、汎用の有機溶媒に対する溶解性に劣るため
に、実用上その改善が強く望まれていた。
また、基板上に成膜して使用する場合、塗膜が
均一に形成できなかつたりして実用に供し得なか
つた。
〔発明の目的〕
本発明の目的は、上記した材料の欠点をなく
し、溶解性が良好で、塗膜が均一に形成でき、か
つ耐熱性にすぐれた塗膜が得られる新規な重合体
を提供するにある。
〔発明の概要〕
上記目的は、高分子主鎖にSi−Si結合と２価の
有機基【式】を含有する
高分子材料によつて達成される。すなわち、上記
目的を達成するために、本発明者はSi−Si結合を
有する重合体を種々合成した結果、下記一般式(1)
で表わされる繰り返し単位よりなり、重量平均分
子量が1000〜1000000である重合体が上記目的を
満足する有用な重合体であることを見い出した。
（但し、一般式(1)中Ｒはエチル基あるいはフエ
ニル基を表わす。）
本発明の重合体は常態で固体であり、トルエ
ン、キシレン等の有機溶剤に容易に溶溶解するの
で、種々の用途に応用できる。例えば、本発明の
重合体は、そのトルエン溶液などを用いてフイル
ム、繊維、シート等に成形することができる。
また、本発明の重合体は、耐熱性、各種金属や
ガラスに対する接着性にすぐれており、絶縁材、
接着剤などとしての利用にも供し得る。
更に本発明の重合体は、機能性高分子材料とし
ても極めて有用である。すなわち、本発明の重合
体は、感光性材料や感放射線材料として有用に用
いられるものである。
本発明の重合体の重量平均分子量は、1000〜
1000000である。1000未満あるいは1000000より大
では、耐熱性、溶解性の点で実用上好ましくな
い。
また、本発明の重合体には、種々の処方に従
い、種々の配合剤、例えば酸化防止剤、熱安定化
剤、着色剤、難燃剤等を配合してもよい。また、
金属などをドーピングすることにより、導電材料
などとしても有用に用いられるものである。
〔発明の実施例〕
以下に本発明の重合体の合成例を、実施例をも
つて具体的に説明するが、本発明は実施例に限定
されるものではない。
実施例 １
ポリ〔ｐ−ビス（メチルフエニルシリルエチニ
ル）ベンゼン〕の合成
冷却器、攪拌機および滴下ロートをつけた500
ml容の三つ口フラスコに、4.0ｇ（0.16ｇ−atom）
のリボン状マグネシウム、乾燥テトラヒドロフラ
ン50mlおよび少量のヨウ素を入れ、これに臭化エ
チルを数滴加えた。
臭化エチルが反応してから、12ｇ（0.15mol）
の塩化イソプロピルを室温で30分かけて加えた。
１時間還流した後、8.1ｇ（0.064mol）の１，４
−ジエチニルベンゼンのテトラヒドロフラン溶液
50mlを室温で30分かけて滴下した。２時間加熱還
流した後、１，２−ジクロロ−１，２−ジメチル
ジフエニルジシラン20ｇ（0.064mol）の50mlテ
トラヒドロフラン溶液を室温で滴下し、その後、
反応混合物を７時間加熱還流した。放冷後水で加
水分解し、有機層を分液した。水層はエーテルで
抽出し、抽出液と有機層を合わせ、水洗した後、
炭素カルシウムで乾燥した。乾燥後、溶媒を留去
してフラスコ残留物をベンゼンに溶かし、濾過し
てからエタノールにより再沈澱を行なつた。二度
再沈澱を行ない、乾燥してから次式で示される淡
黄色粉末状ポリ〔ｐ−ビス（メチルフエニルシリ
ルエチニル）ベンゼン〕7.2ｇを得た。収率は、
31％であつた。
融点は290℃（dec）であり、ｎは27000であ
つた。また、NMRは、1HNMRδ（ppm）：0.65，
0.58（Me Si、6H）7.0〜7.8（phenyl ring
protons、ｍ、14H）であつた。
本重合体はトルエンに溶解し、例えばスピンコ
ーテイング法等により基板上に成膜することがで
きる。本重合体の薄膜に紫外線を照射すると、照
射部が現像液（例えばトルエン１容：イソプロパ
ノール３容の混合溶液）に選択的に可溶化するポ
ジ形レジストとなることが確認され。本重合体は
機能性材料として有用であることが示された。
実施例 ２
ポリ〔ｐ−ビス（エチルメチルシリルエチニ
ル）ベンゼン〕の合成
冷却器、滴下ロートをつけた300ml容の三つ口
フラスコに、80mlのテトラヒドロフランに溶かし
た4.8ｇ（0.038mol）の１，４−ジエチニルベン
ゼンを入れ、窒素気流下でマグネテイツクスター
ラーでかきまぜながら、48ml（0.082mol）のブ
チルリチウム〜ヘキサン溶液を−78℃で滴下し
た。反応混合物を室温になるまでかきまぜ、その
後8.2ｇ（0.082mol）の１，２−ジクロロ−１，
２−ジエチルジメチルジシランを加えた。1.5時
間還流した後、氷冷し、加水分解を行なつた。有
機層を分離し、水洗した後、K2CO3上で乾燥し
た。有機溶媒を留去し、残留物をベンゼンに溶か
し、エタノールから再沈澱を行なつた。二度再沈
澱を行ない、乾燥後、次式で示す淡黄色粉末のポ
リ〔ｐ−ビス（エチルメチルシリルエチニル）ベ
ンゼン〕5.5ｇを得た。収率は、54％であつた。
融点は71〜72℃であり、ｎは7300であつた。
またNMRは、1HNMRδ（ppm）：0.36（MeSi、Ｓ、
6H）、0.71〜1.35（C2H5Si、ｍ、10H）、7.36
（phenyl ring protons、ｓ、4H）であつた。
なお本重合体は実施例１の重合体と同様にポジ
形レジスト材料となることが確認され、機能性材
料として有用であることが示された。
〔発明の効果〕
以上述べましたように本発明の重合体は、溶解
性が良好であり、塗膜が均一に形成でき、かつ耐
熱性にすぐれた塗膜が得られる。
なお、本発明の重合体は、フイルム、シート、
繊維等に成形するとができる。また、本発明の重
合体は絶縁材、接着剤等にも適用できる。
更に本発明の重合体は、機能性高分子材料とし
ても極めて有用である。すなわち、本発明の重合
体は、感光材料や感放射線材料として用いられ
る。 DETAILED DESCRIPTION OF THE INVENTION [Field of Application of the Invention] The present invention relates to a novel polymer that is extremely useful as a functional polymer. For more details, see the general formula below.
This invention relates to a novel polymer consisting of repeating units represented by (1) and having a weight average molecular weight of 1,000 to 1,000,000. (However, R in general formula (1) represents an ethyl group or a phenyl group.) [Background of the Invention] Polymers having Si-Si bonds and divalent organic groups in the polymer main chain are used as photosensitive materials and It is an extremely useful material as an insulating material. This type of polymer is described in Journal of Polymer Science, Polymer Letters Edition (J.Polymer Sci., Polymer Lett.Ed.)
22, 669-671 (1984) have shown polymers consisting of repeating units represented by the following formula (2), but because of their poor solubility in general-purpose organic solvents, there is a strong need for improvement in practical use. It was rare. In addition, when used by forming a film on a substrate, the coating film could not be formed uniformly and could not be put to practical use. [Object of the Invention] The object of the present invention is to provide a novel polymer that eliminates the drawbacks of the above-mentioned materials, has good solubility, can form a uniform coating film, and provides a coating film with excellent heat resistance. There is something to do. [Summary of the Invention] The above object is achieved by a polymer material containing a Si--Si bond and a divalent organic group in the polymer main chain. That is, in order to achieve the above object, the present inventor synthesized various polymers having Si--Si bonds, and as a result, the following general formula (1) was obtained.
It has been found that a polymer consisting of repeating units represented by the following and having a weight average molecular weight of 1,000 to 1,000,000 is a useful polymer that satisfies the above object. (However, R in general formula (1) represents an ethyl group or a phenyl group.) The polymer of the present invention is solid in normal state and is easily dissolved in organic solvents such as toluene and xylene, so it can be used for various purposes. It can be applied to For example, the polymer of the present invention can be formed into a film, fiber, sheet, etc. using a toluene solution thereof. In addition, the polymer of the present invention has excellent heat resistance and adhesion to various metals and glass, and can be used as an insulating material.
It can also be used as an adhesive. Furthermore, the polymer of the present invention is extremely useful as a functional polymer material. That is, the polymer of the present invention can be usefully used as a photosensitive material or a radiation-sensitive material. The weight average molecular weight of the polymer of the present invention is from 1000 to
1000000. If it is less than 1,000 or more than 1,000,000, it is not practically preferred in terms of heat resistance and solubility. Furthermore, various compounding agents such as antioxidants, heat stabilizers, colorants, flame retardants, etc. may be added to the polymer of the present invention according to various formulations. Also,
By doping with metal or the like, it can be usefully used as a conductive material. [Examples of the Invention] Synthesis examples of the polymer of the present invention will be specifically explained below using Examples, but the present invention is not limited to the Examples. Example 1 Synthesis of poly[p-bis(methylphenylsilylethynyl)benzene] 500 with condenser, stirrer and dropping funnel
4.0g (0.16g-atom) in a ml three-necked flask
A ribbon of magnesium, 50 ml of dry tetrahydrofuran, and a small amount of iodine were added, and a few drops of ethyl bromide were added thereto. After the reaction of ethyl bromide, 12g (0.15mol)
of isopropyl chloride was added over 30 minutes at room temperature.
After refluxing for 1 hour, 8.1 g (0.064 mol) of 1,4
-Diethynylbenzene in tetrahydrofuran solution
50 ml was added dropwise over 30 minutes at room temperature. After heating under reflux for 2 hours, a solution of 20 g (0.064 mol) of 1,2-dichloro-1,2-dimethyldiphenyldisilane in 50 ml of tetrahydrofuran was added dropwise at room temperature, and then,
The reaction mixture was heated to reflux for 7 hours. After cooling, it was hydrolyzed with water and the organic layer was separated. The aqueous layer was extracted with ether, and the extract and organic layer were combined and washed with water.
Dried with carbon calcium. After drying, the solvent was distilled off, the flask residue was dissolved in benzene, filtered, and reprecipitated with ethanol. After performing reprecipitation twice and drying, 7.2 g of pale yellow powdered poly[p-bis(methylphenylsilylethynyl)benzene] represented by the following formula was obtained. The yield is
It was 31%. The melting point was 290°C (dec) and n was 27,000. In addition, NMR is 1 HNMRδ (ppm): 0.65,
0.58 (Me Si, 6H) 7.0~7.8 (phenyl ring
protons, m, 14H). This polymer can be dissolved in toluene and formed into a film on a substrate by, for example, a spin coating method. It has been confirmed that when a thin film of this polymer is irradiated with ultraviolet rays, the irradiated area becomes a positive resist that is selectively solubilized in a developer (for example, a mixed solution of 1 volume of toluene and 3 volumes of isopropanol). This polymer was shown to be useful as a functional material. Example 2 Synthesis of poly[p-bis(ethylmethylsilylethynyl)benzene] In a 300 ml three-necked flask equipped with a condenser and a dropping funnel, 4.8 g (0.038 mol) of 1, dissolved in 80 ml of tetrahydrofuran was added. 4-diethynylbenzene was added, and 48 ml (0.082 mol) of a butyllithium-hexane solution was added dropwise at -78°C while stirring with a magnetic stirrer under a nitrogen stream. The reaction mixture was stirred to room temperature and then 8.2 g (0.082 mol) of 1,2-dichloro-1,
2-Diethyldimethyldisilane was added. After refluxing for 1.5 hours, the mixture was cooled on ice and hydrolysis was performed. The organic layer was separated, washed with water, and then dried over K2CO3 . The organic solvent was distilled off, the residue was dissolved in benzene, and reprecipitation was performed from ethanol. After reprecipitation was carried out twice and dried, 5.5 g of poly[p-bis(ethylmethylsilylethynyl)benzene] as a pale yellow powder represented by the following formula was obtained. The yield was 54%. The melting point was 71-72°C and n was 7300.
In addition, NMR is 1 HNMRδ (ppm): 0.36 (MeSi, S,
6H) , 0.71-1.35 ( C2H5Si , m, 10H), 7.36
(phenyl ring protons, s, 4H). It was confirmed that this polymer was a positive resist material like the polymer of Example 1, and was shown to be useful as a functional material. [Effects of the Invention] As described above, the polymer of the present invention has good solubility, can form a uniform coating film, and can provide a coating film with excellent heat resistance. In addition, the polymer of the present invention can be used in films, sheets,
It can be formed into fibers, etc. Furthermore, the polymer of the present invention can be applied to insulating materials, adhesives, and the like. Furthermore, the polymer of the present invention is extremely useful as a functional polymer material. That is, the polymer of the present invention is used as a photosensitive material or a radiation-sensitive material.
Claims (1)
なり、重量平均分子量が1000〜1000000であるこ
とを特徴とする新規な重合体。 （但し、一般式(1)中Ｒはエチル基、あるいはフ
エニル基を表わす）[Scope of Claims] 1. A novel polymer comprising repeating units represented by the following general formula (1) and having a weight average molecular weight of 1,000 to 1,000,000. (However, R in general formula (1) represents an ethyl group or a phenyl group)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60174273A JPS6234923A (en) | 1985-08-09 | 1985-08-09 | Novel polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60174273A JPS6234923A (en) | 1985-08-09 | 1985-08-09 | Novel polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6234923A JPS6234923A (en) | 1987-02-14 |
| JPH0562615B2 true JPH0562615B2 (en) | 1993-09-08 |
Family
ID=15975771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60174273A Granted JPS6234923A (en) | 1985-08-09 | 1985-08-09 | Novel polymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6234923A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2646162B1 (en) * | 1989-04-21 | 1993-01-08 | Rhone Poulenc Chimie | PROCESS FOR THE PREPARATION OF POLYSILYLPOLYYNES AND POLYMERS OBTAINED AT THE END OF THIS PROCESS |
| JP2776184B2 (en) * | 1993-01-25 | 1998-07-16 | 信越化学工業株式会社 | Silicon polymer compound |
| US5512269A (en) * | 1993-06-09 | 1996-04-30 | Burroughs Wellcome, Co. | Method of treating retained pulmonary secretions |
| FR2798662B1 (en) * | 1999-09-16 | 2002-01-18 | Commissariat Energie Atomique | POLY (ETHYNYLENE PHENYLENE ETHYNYLENE SILYLENES) AND PROCESSES FOR THEIR PREPARATION |
| US6271280B1 (en) * | 2000-04-19 | 2001-08-07 | General Electric Company | Diacetylenic polyorganosiloxanes, intermediates therefor, and cured compositions prepared therefrom |
| JP4639915B2 (en) * | 2005-04-01 | 2011-02-23 | Ｊｓｒ株式会社 | Composition for resist underlayer film |
-
1985
- 1985-08-09 JP JP60174273A patent/JPS6234923A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6234923A (en) | 1987-02-14 |
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| LAPS | Cancellation because of no payment of annual fees |