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US4748228A
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Process for producing organic silicon-terminated polyimide precursor and polyimide
Assignee: Hitachi Ltd
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Filing: 1986-05-14
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Granted: 1988-05-31
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Expires: 2006-05-14
Abstract
Abstract An organic silicon-terminated polyimide precursor having a very stable solution viscosity is produced by polycondensing 100 parts by weight of a mixture composed of 90 to 99.5% by mole of an organic diamine represented by the following general formula (I) and 10 to 0.5% by weight by mole of an organic silyl represented by the following general formula (II): H2NR1NH2 (I) <IMAGE> (II) wherein R1 and R2 are divalent organic groups; R3 and R4 are monovalent organic groups; m is 0, 1, 2, or 3, with an organic tetracarboxylic acid dianhydride represented by the following general formula (III) in a molar amount corresponding to the 100 parts by weight of the mixture of the organic diamine and the organic silyl represented by the said general formulae (I) and (II), respectively, in an organic polar solvent at 0 DEG to 40 DEG C., thereby obtaining a solution of organic silicon-terminated polyimide precursor, and heating the solution at 50 DEG to 80 DEG C.: <IMAGE> (III) wherein R5 is a tetravelent organic group. The polyimide having good adhesion and mechanical characteristics is obtained by further heating the precursor solution at 100 DEG to 450 DEG C.
Inventors
- 👤 Fusaji Shoji
- 👤 Haruhiko Matsuyama
- 👤 Akio Fujiwara
- 👤 Fumio Kataoka
- 👤 Teruji Aizawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 21:35
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1003; C08G73/1007; C08G73/101; C08G73/1017
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
168 words
A process for producing an organic silicon-terminated polyimide precursor, which comprises polycondensing 100 parts by weight of a mixture composed of 90 to 99.5% by mole of an organic diamine represented by the following general formula (I) and 10 to 0.5% by mole of an organic silyl represented by the following general formula (II): ##STR5## wherein R 1 and R 2 are divalent organic groups; R 3 and R 4 are monovalent organic groups; m is 0, 1, 2 or 3, with an organic tetracarboxylic acid dianhydride represented by the following general formula (III) in a molar amount corresponding to the 100 parts by weight of the mixture of the organic diamine and the organic silyl represented by the said general formulae (I) and (II), respectively, in an organic polar solvent at 0° to 40° C., thereby obtaining a solution of organic silicon-terminated polyimide precursor, and heating the solution of organic silicon-terminated polyimide precursor at 50° to 80° C.: ##STR6## wherein R 5 is a tetravalent organic group.
Claim 2
Dependent Claim
168 words
A process for producing an organic silicon-terminated polyimide precursor, which comprises polycondensing 100 parts by weight of a mixture composed of 90 to 99.5% by mole of an organic diamine represented by the following general formula (I) and 10 to 0.5% by mole of an organic silyl represented by the following general formula (II): ##STR5## wherein R 1 and R 2 are divalent organic groups; R 3 and R 4 are monovalent organic groups; m is 0, 1, 2 or 3, with an organic tetracarboxylic acid dianhydride represented by the following general formula (III) in a molar amount corresponding to the 100 parts by weight of the mixture of the organic diamine and the organic silyl represented by the said general formulae (I) and (II), respectively, in an organic polar solvent at 0° to 40° C., thereby obtaining a solution of organic silicon-terminated polyimide precursor, and heating the solution of organic silicon-terminated polyimide precursor at 50° to 80° C.: ##STR6## wherein R 5 is a tetravalent organic group.
Claim 3
Dependent Claim
59 words
A process according to claim 1, wherein the organic diamine represented by the said general formula (I) is at least one compound selected from 4,4'-diaminodiphenylether, 3,4'-diaminodiphenylether, 3,3'-diaminodiphenylether, p-phenylenediamine, m-phenylenediamine, 2,4-diaminotoluene, 2,4-diaminoxylene, 3,5,3',5'-tetramethylbenzidine, benzidine, 3,3'-dimethylbenzidine, 1,5-naphthalenediamine, 4,4'-diaminobenzophenone, 3,3'-diaminobenzophenone, or at least one compound selected from 4,4'-diaminodiphenylether-3-carboxylamide, 3,4'-diaminodiphenylether-3-carboxylamide, and 3,3'-diaminodiphenylether-3-carboxylamide, or at least one compound selected from 4,4'-diaminodiphenylmethane, 3,3'-diaminodiphenylmethane, and 4,4'-diaminodiphenylsulfone.
Claim 4
Dependent Claim
50 words
A process according to claim 1, wherein the organic silyl represented by the said general formula (II) is at least one compound selected from 3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane, 3-aminopropylmethoxydimethylsilane, 3-aminopropyltrimethylsilane, 3-aminopropyltriethoxysilane, 3-aminopropyldiethoxysilane, 3-aminopropylethoxydimethylsilane, 3-aminopropyl-tri-n-propoxysilane, 3-aminopropyl-di-n-propoxymethylsilane, 3-aminopropyl-n-propoxymethylsilane, 3-aminopropyl-tri-n-butoxysilane, 3-aminopropyl-di-n-butoxymethylsilane, 3-aminopropyl-n-butoxydimethylsilane, m-aminophenyltrimethoxysilane, m-aminophenyldimethoxymethylsilane, m-aminophenylmethoxymethylsilane, m-aminophenyltrimethylsilane, [3-(p-aminophenoxy)-propyl]-di-n-propoxymethylsilane, [3-(m-aminophenoxy)-propyl]-di-n-butoxymethylsilane, p-aminophenyl-tri-n-propoxysilane, p-aminophenyl-di-n-propoxymethylsilane, p-aminophenyl-n-propoxydimethylsilane, m-aminophenyl-tri-n-propoxysilane, m-aminophenyldi-n-propoxymethylsilane, and m-aminophenyl-n-propoxydimethylsilane.
Claim 5
Dependent Claim
45 words
A process according to claim 1, wherein the organic tetracarboxylic acid dianhydride represented by the said general formula (III) is at least one compound selected from pyromellitic acid dianhydride, 3,3',4,4'-biphenyltetracarboxylic acid dianhydride, 3,3',4,4'-benzophenonetetracarboxylic acid dianhydride, 2,3,3',4'-biphenyltetracarboxylic acid dianhydride, cyclopentanetetracarboxylic acid dianhydride, and 3,3',4,4'-biphenylethertetracarboxylic acid dianhydride.
Claim 6
Dependent Claim
23 words
A process according to claim 1, wherein the organic polar solvent is at least one compound selected from N-methyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide, and N,N-diethylformamide.
Claim 7
Dependent Claim
39 words
A process according to claim 1, wherein the solution of organic silicon-terminated polyimide precursor is composed of 5 to 30% by weight of the organic silicon-terminated polyimide precursor and 95 to 70% by weight of the organic polar solvent.
Claim 8
Dependent Claim
178 words
A process for producing a polyimide, which comprises polycondensing 100 parts by weight of a mixture composed of 90 to 99.5% by mole of an organic diamine represented by the following general formula (I) and 10 to 0.5% by mole of an organic silyl represented by the following general formula (II): ##STR7## wherein R 1 and R 2 are divalent organic groups; R 3 and R 4 are monovalent organic groups; m is 0, 1, 2 or 3, with an organic tetracarboxylic acid dianhydride represented by the following general formula (III) in a molar amount corresponding to the 100 parts by weight of the mixture of the organic diamine and the organic silyl represented by the said general formulae (I) and (II), respectively, in an organic polar solvent at 0° to 40° C., thereby obtaining a solution of organic silicon-terminated polyimide precursor, heating the solution of organic silicon-terminated polyimide precursor at 50° to 80° C., and further heating the solution at 100° to 450° C., thereby curing the precursor: ##STR8## wherein R 5 is a tetravalent organic group.
Claim 9
Dependent Claim
178 words
A process for producing a polyimide, which comprises polycondensing 100 parts by weight of a mixture composed of 90 to 99.5% by mole of an organic diamine represented by the following general formula (I) and 10 to 0.5% by mole of an organic silyl represented by the following general formula (II): ##STR7## wherein R 1 and R 2 are divalent organic groups; R 3 and R 4 are monovalent organic groups; m is 0, 1, 2 or 3, with an organic tetracarboxylic acid dianhydride represented by the following general formula (III) in a molar amount corresponding to the 100 parts by weight of the mixture of the organic diamine and the organic silyl represented by the said general formulae (I) and (II), respectively, in an organic polar solvent at 0° to 40° C., thereby obtaining a solution of organic silicon-terminated polyimide precursor, heating the solution of organic silicon-terminated polyimide precursor at 50° to 80° C., and further heating the solution at 100° to 450° C., thereby curing the precursor: ##STR8## wherein R 5 is a tetravalent organic group.
Claim 10
Dependent Claim
59 words
A process according to claim 7, wherein the organic diamine represented by the said general formula (I) is at least one compound selected from 4,4'-diaminodiphenylether, 3,4'-diaminodiphenylether, 3,3'-diaminodiphenylether, p-phenylenediamine, m-phenylenediamine, 2,4-diaminotoluene, 2,4-diaminoxylene, 3,5,3',5'-tetramethylbenzidine, benzidine, 3,3'-dimethylbenzidine, 1,5-naphthalenediamine, 4,4'-diaminobenzophenone, 3,3'-diaminobenzophenone, or at least one compound selected from 4,4'-diaminodiphenylether-3carboxylamide, 3,4'-diaminodiphenylether-3-carboxylamide, and 3,3'-diaminodiphenylether-3-carboxylamide, or at least one compound selected from 4,4'-diaminodiphenylmethane, 3,3'-diaminodiphenylmethane, and 4,4'-diaminodiphenylsulfone.
Claim 11
Dependent Claim
50 words
A process according to claim 7, wherein the organic silyl represented by the said general formula (II) is at least one compound selected from 3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane, 3-aminopropylmethoxydimethylsilane, 3-aminopropyltrimethylsilane, 3-aminopropyltriethoxysilane, 3-aminopropyldiethoxymethylsilane, 3-aminopropylethoxydimethylsilane, 3-aminopropyl-tri-n-propoxysilane, 3-aminopropyl-di-n-propoxydimethylsilane, 3-aminopropyl-n-propoxysilane, 3-aminopropyl-tri-n-butoxysilane, 3-aminopropyl-di-n-butoxymethylsilane, 3-aminopropyl-n-butoxydimethylsilane, m-aminophenyltrimethoxysilane, m-aminophenyldimethoxymethylsilane, m-aminophenylmethoxymethylsilane, m-aminophenyltrimethylsilane, [3-(p-aminophenoxy)-propyl]-di-n-propoxymethylsilane, [3-(m-aminophenoxy)-propyl]-di-n-butoxymethylsilane, p-aminophenyl-tri-n-propoxysilane, p-aminophenyl-di-n-propoxymethylsilane, p-aminophenyl-n-propoxydimethylsilane, m-aminophenyl-tri-n-propoxysilane, m-aminophenyl-di-n-propoxymethylsilane, and m-aminophenyl-n-propoxydimethylsilane.
Claim 12
Dependent Claim
45 words
A process according to claim 7, wherein the organic tetracarboxylic acid dianhydride represented by the said general formula (III) is at least one compound selected from pyromellitic acid dianhydride, 3,3',4,4'-biphenyltetracarboxylic acid dianhydride, 2,3,3',4'-biphenyltetracarboxylic acid dianhydride, 3,3',4,4'-benzophenonetetracarboxylic acid dianhydride, cyclopentanetetracarboxylic acid dianhydride, and 3,3',4,4'-biphenylethertetracarboxylic acid dianhydride.
Claim 13
Dependent Claim
23 words
A process according to claim 7, wherein the organic polar solvent is at least one compound selected from N-methyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide, and N,N-diethylformamide.
Claim 14
Dependent Claim
39 words
A process according to claim 7, wherein the solution of organic silicon-terminated polyamide precursor is composed of 5 to 30% by weight of the organic silicon-terminated polyimide precursor and 95 to 70% by weight of the organic polar solvent.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-05-31 | 1991-11-30 | 1992-05-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-05-31 | 1995-11-30 | 1996-05-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-05-31 | 1999-11-30 | 2000-05-31 | $7700.00 | Window Closed / Lapsed |