JPS6086017A - Production of polyhydrogen silsesquioxane - Google Patents
Production of polyhydrogen silsesquioxaneInfo
- Publication number
- JPS6086017A JPS6086017A JP19248883A JP19248883A JPS6086017A JP S6086017 A JPS6086017 A JP S6086017A JP 19248883 A JP19248883 A JP 19248883A JP 19248883 A JP19248883 A JP 19248883A JP S6086017 A JPS6086017 A JP S6086017A
- Authority
- JP
- Japan
- Prior art keywords
- trichlorosilane
- water
- silsesquioxane
- inert gas
- solution
- 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.)
- Pending
Links
Landscapes
- Silicon Compounds (AREA)
- Silicon Polymers (AREA)
- Formation Of Insulating Films (AREA)
Abstract
Description
【発明の詳細な説明】
技術分野
本発明は、特に溶剤に可溶なポリジハイドロジェンシル
セスキオキサンの製法に関する。DETAILED DESCRIPTION OF THE INVENTION TECHNICAL FIELD The present invention relates in particular to a process for making polydihydrogensilsesquioxanes that are soluble in solvents.
ポリハイドロジエンシルセスキオキサンは、従来の製法
として、トリクロルシランを適当な溶剤に溶解した後、
これに多量の水を加えて加水分解し、引続いて縮重合さ
せる。Polyhydrodiene silsesquioxane is conventionally produced by dissolving trichlorosilane in a suitable solvent,
A large amount of water is added to this for hydrolysis, followed by polycondensation.
Ｈ８１Ｃ／４＋３ＨｚＯ→Ｈ８１（ＯＨ）３＋３ＨＣｔ
１
反応中に、加水分解によって塩酸酸性となり、発熱を伴
なう。このため、ＨｘＳｉＣＬ、の５ｔ−Ｈ結合が分解
して三次元架橋し、ゲル化するので溶剤に可溶なものを
得ることができなかった。H81C/4+3HzO→H81(OH)3+3HCt
1 During the reaction, hydrochloric acid becomes acidic due to hydrolysis, accompanied by heat generation. For this reason, the 5t-H bond of HxSiCL decomposes, three-dimensionally crosslinks, and gels, making it impossible to obtain a solvent-soluble product.
発明の目的
本発明の目的Ｆｉ溶剤に可溶なポリジハイドロジェンシ
ルセスキオキサンの製法を提供することである。OBJECTS OF THE INVENTION It is an object of the present invention to provide a method for producing polydihydrogensilsesquioxane soluble in Fi solvents.
発明の構成
本発明の上記目的は、予め水を飽和し良溶剤にトリクロ
ルシランを溶解して溶液とし、水蒸気を同伴する不活性
ガスをこの溶液にバブリングすることを特徴とする、ポ
リジハイドロジェンシルセスキオキサンの製法によって
達成される。Structure of the Invention The above object of the present invention is to prepare a polydihydrogensil, which is characterized in that trichlorosilane is dissolved in a good solvent saturated with water to form a solution, and an inert gas accompanied by water vapor is bubbled into this solution. This is achieved by the production method of sesquioxane.
ボリジハイドロジヱンシルセスキオキサンの溶剤は芳香
族炭化水素または脂肪族ケトンであり、ベンゼン、トル
エン、メチルイソブチルケトンまたはメチルエチルケト
ンが代表的であって、これらの溶剤によく溶解する。ま
たこの重合体をシリル化した、たとえばジメチルシリル
末端ポリジハイドロジェンシルセスキオキサンも、これ
らの溶剤によく溶解する。The solvent for boridihydrodiene silsesquioxane is an aromatic hydrocarbon or aliphatic ketone, typically benzene, toluene, methyl isobutyl ketone or methyl ethyl ketone, and it is well soluble in these solvents. Furthermore, silylated versions of this polymer, such as dimethylsilyl-terminated polydihydrogensilsesquioxane, are also well soluble in these solvents.
本発明の製法において、トリクロルシラ７倉溶解する予
め水を飽和した溶剤はメチルイソブチルケトンが適当で
あり、これに温度ｌｏ℃において水層２重量％を溶解し
て飽和させる。このとき、水層全分離させないことが重
要であって、もし水層を伴なうときは、トリクロルシラ
ンおよび水を溶解して含む有機層と水層との界面におい
て水素の気泡を発生し、得られた縮重合物はゲル化して
、溶剤に不溶となる。In the production method of the present invention, methyl isobutyl ketone is suitably used as the solvent previously saturated with water in which 7 volumes of trichlorosilica are dissolved, and 2% by weight of the water layer is dissolved therein at a temperature of 10° C. to saturate the solvent. At this time, it is important not to completely separate the aqueous layer; if the aqueous layer is present, hydrogen bubbles will be generated at the interface between the aqueous layer and the organic layer containing dissolved trichlorosilane and water. The resulting polycondensation product gels and becomes insoluble in solvents.
水蒸気を同伴する不活性ガスは、たとえば窒素を、温度
５０〜７０℃の水中に通して水蒸気全会ませる口
実施例
２重量係の水を含むメチルイソブチルケトン１２５１氷
冷しながら、トリクロルシラン１３．６ Ｆ （０，１
モル）を徐々に加えて反応液とじ７ｊｏ他方、蒸を水２
００ ｍｌを５０〜７０℃に加熱し、窒素を流速５０
ｍｌ ／ ｍｌ ｎで吹込んで水蒸気を同伴させた。The inert gas accompanied by water vapor is, for example, nitrogen passed through water at a temperature of 50 to 70°C to completely absorb the water vapor. F (0,1
Gradually add 2 moles of water to close the reaction solution.
00 ml to 50-70°C and nitrogen at a flow rate of 50°C.
Water vapor was entrained by blowing in at ml/ml n.
反応液を温度３５℃に加熱し、攪拌しながら水蒸気同伴
窒素をバブリングし続けた０２４時間経過した後にバブ
リングを止め、この温度で１時間５０ ｖｒｎ Ｈｆ
Ｋ減圧して、塩酸および溶剤を運出した。残留液を蒸留
水で水洗して、ポリジノ飄イドロジェンシルセスキオキ
サン約５重量１１含むメチルイソブチルケトン溶液８０
２を得た。これにジメチルクロルシラン９．５ｆ（０，
１モル）を加えて末端のシラノール基をシリル化した。The reaction solution was heated to a temperature of 35°C, and water vapor entrained nitrogen was continued to be bubbled while stirring. After 24 hours, bubbling was stopped, and at this temperature, 50 vrn Hf was heated for 1 hour.
A K vacuum was applied to remove the hydrochloric acid and solvent. The remaining liquid was washed with distilled water to obtain a methyl isobutyl ketone solution containing about 5 parts by weight of polydinohydrogensilsesquioxane, 80 parts by weight.
I got 2. To this was added 9.5f of dimethylchlorosilane (0,
1 mol) was added to silylate the terminal silanol group.
水５０Ｆを滴下して過剰のシリル化剤を分解させ、水洗
後１．５ｍ１Ｈｆに減圧して溌縮液とし１次いでアセト
ニトリル１５ｆ’Ｔｈ加えて沈澱生成し、ベンゼン２ｆ
”ｆｆ加えて溶解し、さらにアセトニトリル１５ｆを加
えて粉末化のポリジメチルシリル末端ポリジハイドロジ
Ｊ、ルシルセスキオキサン３．５９ｋ”４た０収率は２
６係であった０
このシリル末端ポリハイドロジエンシルセスキオキサン
はベンゼンに可溶であった。50 F of water was added dropwise to decompose the excess silylating agent, and after washing with water, the pressure was reduced to 1.5 mL of 1 Hf to make the liquid. 1. Then, 15 F' of acetonitrile was added to form a precipitate, and 2 F of benzene was added.
``Add ff and dissolve, then add 15f of acetonitrile to powder polydimethylsilyl-terminated polydihydrodiJ, lucylsesquioxane 3.59k'' 4.0 Yield is 2
This silyl-terminated polyhydrodiene silsesquioxane was soluble in benzene.
発明の効果
本発明の製法はトリクロルジノンを級漫に加水分解する
ことにニーて、ゲルイヒさせることなく、ポリジハイド
ロジェンシルセスキオキケンおよびその末端ｔシリル化
した重合体を得ることができるので、これを浴剤に浴フ
弄し１ζ、たとえば半導体装ｔｉｔ絶縁膜用の被験形成
溶液として使用することができる。Effects of the Invention The production method of the present invention allows for the gradual hydrolysis of trichlordinone and the production of polydihydrogensilsesquiokene and its terminal t-silylated polymer without gelation. This can be diluted with a bath agent and used as a test formation solution for, for example, a semiconductor titanium insulating film.
特許出願人 富士通株式会社 特許出願代理人 ヅｆ理士 宵 木 朗 弁理士 西 舘 和 之 弁理士 内 １） 幸 男 弁理士 山 口 昭 之patent applicant Fujitsu Limited patent application agent ㅅf Physician Akira Yoi Patent attorney Kazuyuki Nishidate Patent attorney 1) Yukio Patent attorney Akira Yamaguchi
Claims (1)
て溶液とし、水蒸気を同伴する不活性ガスをこの溶液に
バブリングすることによって、トリクロルシランを加水
分解し、かつ縮重合させることを特徴とする、ポリジノ
・イドロジゴンシルセスキオキサンの製法。1. Trichlorosilane is dissolved in a solvent saturated with water in advance to form a solution, and an inert gas accompanied by water vapor is bubbled into this solution to hydrolyze trichlorosilane and cause condensation polymerization. , a method for producing polydino-hydrodigon silsesquioxane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19248883A JPS6086017A (en) | 1983-10-17 | 1983-10-17 | Production of polyhydrogen silsesquioxane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19248883A JPS6086017A (en) | 1983-10-17 | 1983-10-17 | Production of polyhydrogen silsesquioxane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6086017A true JPS6086017A (en) | 1985-05-15 |
Family
ID=16292131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19248883A Pending JPS6086017A (en) | 1983-10-17 | 1983-10-17 | Production of polyhydrogen silsesquioxane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6086017A (en) |
Cited By (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4999397A (en) * | 1989-07-28 | 1991-03-12 | Dow Corning Corporation | Metastable silane hydrolyzates and process for their preparation |
| US5091162A (en) * | 1990-10-01 | 1992-02-25 | Dow Corning Corporation | Perhydrosiloxane copolymers and their use as coating materials |
| EP0615000A1 (en) | 1993-03-08 | 1994-09-14 | Dow Corning Corporation | Coatings using filled hydrogen silsequioxane |
| US5370904A (en) * | 1992-12-10 | 1994-12-06 | Dow Corning Toray Silicone Co., Ltd. | Method for the formation of silicon oxide films |
| US5370903A (en) * | 1992-12-11 | 1994-12-06 | Dow Corning Toray Silicon Co., Ltd. | Method for the formation of a silicon oxide film |
| US5416190A (en) * | 1992-11-24 | 1995-05-16 | Dow Corning Toray Silicone Co., Ltd. | Method for the molecular weight fractionation of polyhydrogen silsesquioxane |
| US5516867A (en) * | 1995-05-12 | 1996-05-14 | Dow Corning Corporation | Modified hydrogen silsesquioxane resin |
| EP0770652A2 (en) | 1995-10-26 | 1997-05-02 | Dow Corning Corporation | Tamper-proof electronic coatings |
| EP0775680A1 (en) | 1995-11-27 | 1997-05-28 | Dow Corning Corporation | Protective coating for electronic devices |
| EP0778612A2 (en) | 1995-12-04 | 1997-06-11 | Dow Corning Corporation | Method of curing hydrogen silsesquioxane resin by electron beam to convert it to a silica containing ceramic coating |
| US5693565A (en) * | 1996-07-15 | 1997-12-02 | Dow Corning Corporation | Semiconductor chips suitable for known good die testing |
| US5707681A (en) * | 1997-02-07 | 1998-01-13 | Dow Corning Corporation | Method of producing coatings on electronic substrates |
| US5711987A (en) * | 1996-10-04 | 1998-01-27 | Dow Corning Corporation | Electronic coatings |
| US5776235A (en) * | 1996-10-04 | 1998-07-07 | Dow Corning Corporation | Thick opaque ceramic coatings |
| US5780163A (en) * | 1996-06-05 | 1998-07-14 | Dow Corning Corporation | Multilayer coating for microelectronic devices |
| US5906859A (en) * | 1998-07-10 | 1999-05-25 | Dow Corning Corporation | Method for producing low dielectric coatings from hydrogen silsequioxane resin |
| EP1008609A3 (en) * | 1998-12-07 | 2001-03-14 | DOW CORNING ASIA, Ltd. | Process for the preparation of hydrogen silsesquioxane resin and modified hydrogen silsesquioxane resin |
| US6210749B1 (en) | 1997-06-06 | 2001-04-03 | Dow Corning, Corporation | Thermally stable dielectric coatings |
| EP1107330A2 (en) | 1999-12-06 | 2001-06-13 | Dow Corning Corporation | Modification of infrared reflectivity using silicon dioxide thin films derived from silsesquioxane resins |
| US6265086B1 (en) | 1998-06-10 | 2001-07-24 | Dow Corning Limited | Electroless metal deposition on silyl hydride functional resin |
| US6423651B1 (en) | 1993-12-27 | 2002-07-23 | Kawasaki Steel Corporation | Insulating film of semiconductor device and coating solution for forming insulating film and method of manufacturing insulating film |
| US6576300B1 (en) | 2000-03-20 | 2003-06-10 | Dow Corning Corporation | High modulus, low dielectric constant coatings |
| US6756085B2 (en) | 2001-09-14 | 2004-06-29 | Axcelis Technologies, Inc. | Ultraviolet curing processes for advanced low-k materials |
| US6759098B2 (en) * | 2000-03-20 | 2004-07-06 | Axcelis Technologies, Inc. | Plasma curing of MSQ-based porous low-k film materials |
| US6913796B2 (en) * | 2000-03-20 | 2005-07-05 | Axcelis Technologies, Inc. | Plasma curing process for porous low-k materials |
| US7011868B2 (en) | 2000-03-20 | 2006-03-14 | Axcelis Technologies, Inc. | Fluorine-free plasma curing process for porous low-k materials |
| US7737082B2 (en) | 2004-09-17 | 2010-06-15 | James Alan Rabe | Siloxane composition, agglomerate, and method of preparing |
| US8088547B2 (en) | 2004-11-02 | 2012-01-03 | Dow Corning Corporation | Resist composition |
| US8524439B2 (en) | 2006-06-28 | 2013-09-03 | Dow Corning Corporation | Silsesquioxane resin systems with base additives bearing electron-attracting functionalities |
| US10358561B2 (en) | 2014-04-09 | 2019-07-23 | Dow Silicones Corporation | Hydrophobic article |
| US10473822B2 (en) | 2014-04-09 | 2019-11-12 | Dow Silicones Corporation | Optical element |
-
1983
- 1983-10-17 JP JP19248883A patent/JPS6086017A/en active Pending
Cited By (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4999397A (en) * | 1989-07-28 | 1991-03-12 | Dow Corning Corporation | Metastable silane hydrolyzates and process for their preparation |
| US5091162A (en) * | 1990-10-01 | 1992-02-25 | Dow Corning Corporation | Perhydrosiloxane copolymers and their use as coating materials |
| US5416190A (en) * | 1992-11-24 | 1995-05-16 | Dow Corning Toray Silicone Co., Ltd. | Method for the molecular weight fractionation of polyhydrogen silsesquioxane |
| US5486564A (en) * | 1992-11-24 | 1996-01-23 | Dow Corning Toray Silicone Company, Ltd. | High purity polyhydrogen silsesquioxane resin for electronic coatings |
| US5370904A (en) * | 1992-12-10 | 1994-12-06 | Dow Corning Toray Silicone Co., Ltd. | Method for the formation of silicon oxide films |
| US5370903A (en) * | 1992-12-11 | 1994-12-06 | Dow Corning Toray Silicon Co., Ltd. | Method for the formation of a silicon oxide film |
| EP0615000A1 (en) | 1993-03-08 | 1994-09-14 | Dow Corning Corporation | Coatings using filled hydrogen silsequioxane |
| US6423651B1 (en) | 1993-12-27 | 2002-07-23 | Kawasaki Steel Corporation | Insulating film of semiconductor device and coating solution for forming insulating film and method of manufacturing insulating film |
| US6828258B2 (en) | 1993-12-27 | 2004-12-07 | Kawasaki Microelectronics, Inc. | Method of forming an insulating film having SI-C, SI-O and SI-H bonds to cover wiringlines of a semiconductor device |
| US5516867A (en) * | 1995-05-12 | 1996-05-14 | Dow Corning Corporation | Modified hydrogen silsesquioxane resin |
| EP0770652A2 (en) | 1995-10-26 | 1997-05-02 | Dow Corning Corporation | Tamper-proof electronic coatings |
| EP0775680A1 (en) | 1995-11-27 | 1997-05-28 | Dow Corning Corporation | Protective coating for electronic devices |
| EP0778612A2 (en) | 1995-12-04 | 1997-06-11 | Dow Corning Corporation | Method of curing hydrogen silsesquioxane resin by electron beam to convert it to a silica containing ceramic coating |
| US5780163A (en) * | 1996-06-05 | 1998-07-14 | Dow Corning Corporation | Multilayer coating for microelectronic devices |
| US5693565A (en) * | 1996-07-15 | 1997-12-02 | Dow Corning Corporation | Semiconductor chips suitable for known good die testing |
| US5711987A (en) * | 1996-10-04 | 1998-01-27 | Dow Corning Corporation | Electronic coatings |
| US5776235A (en) * | 1996-10-04 | 1998-07-07 | Dow Corning Corporation | Thick opaque ceramic coatings |
| US6144106A (en) * | 1996-10-04 | 2000-11-07 | Dow Corning Corporation | Electronic coatings |
| US5707681A (en) * | 1997-02-07 | 1998-01-13 | Dow Corning Corporation | Method of producing coatings on electronic substrates |
| US6210749B1 (en) | 1997-06-06 | 2001-04-03 | Dow Corning, Corporation | Thermally stable dielectric coatings |
| US6265086B1 (en) | 1998-06-10 | 2001-07-24 | Dow Corning Limited | Electroless metal deposition on silyl hydride functional resin |
| US5906859A (en) * | 1998-07-10 | 1999-05-25 | Dow Corning Corporation | Method for producing low dielectric coatings from hydrogen silsequioxane resin |
| EP1008609A3 (en) * | 1998-12-07 | 2001-03-14 | DOW CORNING ASIA, Ltd. | Process for the preparation of hydrogen silsesquioxane resin and modified hydrogen silsesquioxane resin |
| EP1107330A2 (en) | 1999-12-06 | 2001-06-13 | Dow Corning Corporation | Modification of infrared reflectivity using silicon dioxide thin films derived from silsesquioxane resins |
| US6576300B1 (en) | 2000-03-20 | 2003-06-10 | Dow Corning Corporation | High modulus, low dielectric constant coatings |
| US6759098B2 (en) * | 2000-03-20 | 2004-07-06 | Axcelis Technologies, Inc. | Plasma curing of MSQ-based porous low-k film materials |
| US6913796B2 (en) * | 2000-03-20 | 2005-07-05 | Axcelis Technologies, Inc. | Plasma curing process for porous low-k materials |
| US7011868B2 (en) | 2000-03-20 | 2006-03-14 | Axcelis Technologies, Inc. | Fluorine-free plasma curing process for porous low-k materials |
| US6756085B2 (en) | 2001-09-14 | 2004-06-29 | Axcelis Technologies, Inc. | Ultraviolet curing processes for advanced low-k materials |
| US7737082B2 (en) | 2004-09-17 | 2010-06-15 | James Alan Rabe | Siloxane composition, agglomerate, and method of preparing |
| US8088547B2 (en) | 2004-11-02 | 2012-01-03 | Dow Corning Corporation | Resist composition |
| US8524439B2 (en) | 2006-06-28 | 2013-09-03 | Dow Corning Corporation | Silsesquioxane resin systems with base additives bearing electron-attracting functionalities |
| US10358561B2 (en) | 2014-04-09 | 2019-07-23 | Dow Silicones Corporation | Hydrophobic article |
| US10473822B2 (en) | 2014-04-09 | 2019-11-12 | Dow Silicones Corporation | Optical element |
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