JPS6222830A - 珪素含有ポリイミド樹脂の製造法 - Google Patents
珪素含有ポリイミド樹脂の製造法Info
- Publication number
- JPS6222830A JPS6222830A JP16265985A JP16265985A JPS6222830A JP S6222830 A JPS6222830 A JP S6222830A JP 16265985 A JP16265985 A JP 16265985A JP 16265985 A JP16265985 A JP 16265985A JP S6222830 A JPS6222830 A JP S6222830A
- Authority
- JP
- Japan
- Prior art keywords
- polyimide resin
- tetrahydrophthalic anhydride
- diamine
- silicon
- mol
- 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
- 229920001721 polyimide Polymers 0.000 title claims abstract description 39
- 239000009719 polyimide resin Substances 0.000 title claims abstract description 38
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 15
- 239000010703 silicon Substances 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 229920005575 poly(amic acid) Polymers 0.000 claims abstract description 23
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 20
- 150000004985 diamines Chemical class 0.000 claims abstract description 17
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 claims abstract description 9
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 21
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 19
- 230000018044 dehydration Effects 0.000 abstract description 6
- 238000006297 dehydration reaction Methods 0.000 abstract description 6
- 239000011347 resin Substances 0.000 abstract description 5
- 229920005989 resin Polymers 0.000 abstract description 5
- -1 tetracarboxylic acid dianhydride Chemical class 0.000 abstract description 5
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 abstract description 4
- 230000000379 polymerizing effect Effects 0.000 abstract description 3
- 150000000000 tetracarboxylic acids Chemical class 0.000 abstract description 3
- 238000005299 abrasion Methods 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 description 14
- 238000000576 coating method Methods 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 8
- 239000000919 ceramic Substances 0.000 description 5
- 239000007822 coupling agent Substances 0.000 description 5
- 235000012431 wafers Nutrition 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FHBXQJDYHHJCIF-UHFFFAOYSA-N (2,3-diaminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FHBXQJDYHHJCIF-UHFFFAOYSA-N 0.000 description 1
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UHMARZNHEMRXQH-UHFFFAOYSA-N 3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1=CCCC2C(=O)OC(=O)C21 UHMARZNHEMRXQH-UHFFFAOYSA-N 0.000 description 1
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 description 1
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 1
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 1
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 description 1
- FIQYGSFMYQTTET-UHFFFAOYSA-N 5-tributoxysilyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C([Si](OCCCC)(OCCCC)OCCCC)=CCC2C(=O)OC(=O)C12 FIQYGSFMYQTTET-UHFFFAOYSA-N 0.000 description 1
- LPFHTHNBDUYRLN-UHFFFAOYSA-N 5-triethoxysilyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C([Si](OCC)(OCC)OCC)=CCC2C(=O)OC(=O)C12 LPFHTHNBDUYRLN-UHFFFAOYSA-N 0.000 description 1
- JXZIXXKVRPNYNK-UHFFFAOYSA-N 5-trimethoxysilyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C([Si](OC)(OC)OC)=CCC2C(=O)OC(=O)C12 JXZIXXKVRPNYNK-UHFFFAOYSA-N 0.000 description 1
- NOGROPXZRIAJND-UHFFFAOYSA-N 5-tripropoxysilyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C([Si](OCCC)(OCCC)OCCC)=CCC2C(=O)OC(=O)C12 NOGROPXZRIAJND-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 239000011825 aerospace material Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000005260 alpha ray Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- RZIPTXDCNDIINL-UHFFFAOYSA-N cyclohexane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCC1(C(O)=O)C(O)=O RZIPTXDCNDIINL-UHFFFAOYSA-N 0.000 description 1
- STZIXLPVKZUAMV-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1(C(O)=O)C(O)=O STZIXLPVKZUAMV-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000012777 electrically insulating material Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 229920006015 heat resistant resin Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16265985A JPS6222830A (ja) | 1985-07-23 | 1985-07-23 | 珪素含有ポリイミド樹脂の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16265985A JPS6222830A (ja) | 1985-07-23 | 1985-07-23 | 珪素含有ポリイミド樹脂の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6222830A true JPS6222830A (ja) | 1987-01-31 |
| JPH0211616B2 JPH0211616B2 (enrdf_load_stackoverflow) | 1990-03-15 |
Family
ID=15758834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16265985A Granted JPS6222830A (ja) | 1985-07-23 | 1985-07-23 | 珪素含有ポリイミド樹脂の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6222830A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0491130A (ja) * | 1990-08-06 | 1992-03-24 | Shin Etsu Chem Co Ltd | 硬化性樹脂溶液組成物及びその製造方法並びに電子部品用保護膜 |
| JPH0489827A (ja) * | 1990-08-03 | 1992-03-24 | Shin Etsu Chem Co Ltd | ポリアミド酸共重合体及びその製造方法 |
| JPH04351667A (ja) * | 1991-05-29 | 1992-12-07 | Shin Etsu Chem Co Ltd | 硬化性樹脂組成物及び電子部品用保護膜 |
| US5262505A (en) * | 1991-07-30 | 1993-11-16 | Dow Corning Toray Silicone Co. Ltd. | Silicone modified polyimide resin and method for preparing same |
| WO2006118353A1 (ja) * | 2005-05-02 | 2006-11-09 | Soken Chemical & Engineering Co., Ltd. | 耐熱性と接着性とに優れた樹脂組成物及びその製造方法 |
| US12068108B2 (en) | 2018-12-10 | 2024-08-20 | Panasonic Intellectual Property Management Co., Ltd. | Electrochemical device electrode and electrochemical device |
-
1985
- 1985-07-23 JP JP16265985A patent/JPS6222830A/ja active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0489827A (ja) * | 1990-08-03 | 1992-03-24 | Shin Etsu Chem Co Ltd | ポリアミド酸共重合体及びその製造方法 |
| JPH0491130A (ja) * | 1990-08-06 | 1992-03-24 | Shin Etsu Chem Co Ltd | 硬化性樹脂溶液組成物及びその製造方法並びに電子部品用保護膜 |
| JPH04351667A (ja) * | 1991-05-29 | 1992-12-07 | Shin Etsu Chem Co Ltd | 硬化性樹脂組成物及び電子部品用保護膜 |
| US5262505A (en) * | 1991-07-30 | 1993-11-16 | Dow Corning Toray Silicone Co. Ltd. | Silicone modified polyimide resin and method for preparing same |
| WO2006118353A1 (ja) * | 2005-05-02 | 2006-11-09 | Soken Chemical & Engineering Co., Ltd. | 耐熱性と接着性とに優れた樹脂組成物及びその製造方法 |
| JP5119493B2 (ja) * | 2005-05-02 | 2013-01-16 | 綜研化学株式会社 | 耐熱性と接着性とに優れた樹脂組成物及びその製造方法 |
| US12068108B2 (en) | 2018-12-10 | 2024-08-20 | Panasonic Intellectual Property Management Co., Ltd. | Electrochemical device electrode and electrochemical device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0211616B2 (enrdf_load_stackoverflow) | 1990-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2660884B2 (ja) | シリコーン変性ポリイミド樹脂およびその製造方法 | |
| JPH01217037A (ja) | 低吸湿性かつ高接着性のシリコン含有ポリイミド及びその前駆体の製造方法 | |
| JPH04325523A (ja) | シロキシサン変性ポリイミド樹脂の製造方法 | |
| JPH0267320A (ja) | ２，２―ビス（アミノフェニル）ヘキサフルオロプロパンから誘導したコポリイミド | |
| EP0297756B1 (en) | Processes for producing a silicon-containing polyimide and a precursor therefor | |
| JPS60166325A (ja) | 耐熱性樹脂の製造方法 | |
| JPS60161429A (ja) | 耐熱性樹脂の製造方法 | |
| JPH0292535A (ja) | 金属とポリイミドの複合成形体 | |
| JPS6222830A (ja) | 珪素含有ポリイミド樹脂の製造法 | |
| US5071908A (en) | Silicon polyimide precursor composition | |
| JPS6323928A (ja) | 変性ポリイミドの製造方法 | |
| JPH01129025A (ja) | ポリアミノビスイミド系樹脂組成物 | |
| CN104211881B (zh) | 有机‑无机混成材料薄膜及其制造方法 | |
| EP0419519B1 (en) | Hexafluoroisopropylidene-containing polyimide oligomers and polymers | |
| JPH0214242A (ja) | ポリアミツク酸組成物およびその製造方法 | |
| KR102704985B1 (ko) | 폴리이미드 수지, 이의 제조 방법, 및 이를 포함하는 폴리이미드 필름 및 디스플레이 장치 | |
| JPH0129510B2 (enrdf_load_stackoverflow) | ||
| US5109058A (en) | Curable resin solution compositions, their preparation, and electronic part protective coatings | |
| US3730941A (en) | Polymides from tetrahydrofuran-2,3:4,5-tetracarboxylic acid dianhydrides | |
| JPS5953287B2 (ja) | ポリイミド前駆体の製造法 | |
| JPH03179026A (ja) | 熱硬化性樹脂組成物、樹脂シート、プリプレグ及び積層板 | |
| JPH01143867A (ja) | 新規なイミド化合物並びにその製造方法 | |
| JPS63225629A (ja) | ポリイミド系樹脂 | |
| JPH01163214A (ja) | ポリイミドイソインドロキナゾリンジオン及びその前駆体の製造法 | |
| JPS62270622A (ja) | 相互侵入性高分子網目状ポリイミドおよびその製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |