JPH0374690B2 - - Google Patents

Info

Publication number: JPH0374690B2
Authority: JP; Japan
Prior art keywords: silicon; group; reaction; dianhydride; modified polyimide
Prior art date: 1986-03-31
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

Application number

JP7137886A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62227928A (ja

Priority date (The priority date 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 date listed.)

1986-03-31

Filing date

1986-03-31

Publication date

1991-11-27

1986-03-31 Application filed filed Critical

1986-03-31 Priority to JP7137886A priority Critical patent/JPS62227928A/ja

1987-10-06 Publication of JPS62227928A publication Critical patent/JPS62227928A/ja

1991-11-27 Publication of JPH0374690B2 publication Critical patent/JPH0374690B2/ja

Status Granted legal-status Critical Current

Links

-1 diamine compound Chemical class 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
229920001721 polyimide Polymers 0.000 description 29
239000004642 Polyimide Substances 0.000 description 26
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 description 19
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 10
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 10
229910052710 silicon Inorganic materials 0.000 description 10
239000010703 silicon Substances 0.000 description 10
125000006158 tetracarboxylic acid group Chemical group 0.000 description 10
239000002904 solvent Substances 0.000 description 9
CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 5
150000004984 aromatic diamines Chemical class 0.000 description 5
150000004985 diamines Chemical class 0.000 description 5
238000000034 method Methods 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 4
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 3
DSWXRFLBTHXQCC-UHFFFAOYSA-N 4-bromo-1,2-dihydroacenaphthylene Chemical compound C1=CC2=CC(Br)=CC(CC3)=C2C3=C1 DSWXRFLBTHXQCC-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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
125000004432 carbon atom Chemical group C* 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical class C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
239000002798 polar solvent Substances 0.000 description 3
239000009719 polyimide resin Substances 0.000 description 3
229920001296 polysiloxane Polymers 0.000 description 3
125000005650 substituted phenylene group Chemical group 0.000 description 3
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
RBERQFUZMKLXEG-UHFFFAOYSA-N 4-[(4,5-dicarboxynaphthalen-1-yl)-dimethylsilyl]naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC=C2C([Si](C)(C=3C4=CC=CC(=C4C(C(O)=O)=CC=3)C(O)=O)C)=CC=C(C(O)=O)C2=C1C(O)=O RBERQFUZMKLXEG-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000007818 Grignard reagent Substances 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
IOFKBFCXHMGIPJ-UHFFFAOYSA-N [Li]C=1C=C2CCC=3C=CC=C(C1)C32 Chemical compound [Li]C=1C=C2CCC=3C=CC=C(C1)C32 IOFKBFCXHMGIPJ-UHFFFAOYSA-N 0.000 description 2
125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
238000007112 amidation reaction Methods 0.000 description 2
125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 2
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
150000004795 grignard reagents Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
125000004957 naphthylene 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
238000006068 polycondensation reaction Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
230000004580 weight loss Effects 0.000 description 2
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 1
MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 description 1
JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
ZYEDGEXYGKWJPB-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)(C)C1=CC=C(N)C=C1 ZYEDGEXYGKWJPB-UHFFFAOYSA-N 0.000 description 1
VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-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
238000003747 Grignard reaction Methods 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
230000005260 alpha ray Effects 0.000 description 1
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
125000004427 diamine group Chemical group 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940018564 m-phenylenediamine Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
WSKHYOXDVZCOJP-UHFFFAOYSA-N naphthalene-1,6-diamine Chemical compound NC1=CC=CC2=CC(N)=CC=C21 WSKHYOXDVZCOJP-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229920005575 poly(amic acid) Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004065 semiconductor Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000005760 substituted naphthylene group Chemical group 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000002411 thermogravimetry Methods 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)

JP7137886A 1986-03-31 1986-03-31 シリコン変性ポリイミド Granted JPS62227928A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP7137886A JPS62227928A (ja)	1986-03-31	1986-03-31	シリコン変性ポリイミド

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP7137886A JPS62227928A (ja)	1986-03-31	1986-03-31	シリコン変性ポリイミド

Publications (2)

Publication Number	Publication Date
JPS62227928A JPS62227928A (ja)	1987-10-06
JPH0374690B2 true JPH0374690B2 (fr)	1991-11-27

Family

ID=13458778

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7137886A Granted JPS62227928A (ja)	1986-03-31	1986-03-31	シリコン変性ポリイミド

Country Status (1)

Country	Link
JP (1)	JPS62227928A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2621490B2 (ja) *	1989-07-14	1997-06-18	日立電線株式会社	石英ガラスキャピラリ

1986
- 1986-03-31 JP JP7137886A patent/JPS62227928A/ja active Granted

Also Published As

Publication number	Publication date
JPS62227928A (ja)	1987-10-06

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JP3968835B2 (ja)	2007-08-29	シロキサンポリイミドを含有する耐熱性接着剤
US4672099A (en)	1987-06-09	Soluble polyimide-siloxane precursor, process for producing same and cross-linked polyimide-siloxane
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JPH0374690B2 (fr)	1991-11-27
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JP2628322B2 (ja)	1997-07-09	シリコン含有可溶性ポリイミド前駆体及びその製造法
JPH0142969B2 (fr)	1989-09-18
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