US4499252A
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Process for producing polyimide precursor
Assignee: Nitto Denko Corp
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Filing: 1984-03-28
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Granted: 1985-02-12
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Expires: 2004-03-28
Abstract
Abstract A process for producing a polyimide precursor having excellent adhesion property and improved moisture resistance by polymerization of an organic tetracarboxylic acid component and a diamine is disclosed. A portion of the organic tetracarboxylic acid is reacted with an aminosilane compound in which H in an amino group is substituted with a monovalent organic group containing a hydrophobic aromatic ring, to produce a silane-modified polycarboxylic acid component and the resulting silane-modified polycarboxylic acid component is polymerized with a diamine together with the residual organic tetracarboxylic acid component.
Inventors
- 👤 Kazumasa Igarashi
- 👤 Katsuhiko Yamaguchi
- 👤 Munekazu Tanaka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 23:44
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1057; C08G73/106
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
249 words
A process for producing a polyimide precursor by polymerizing an organic tetracarboxylic acid component and a diamine, which comprises reacting a portion of an organic tetracarboxylic acid component with an aminosilane compound represented by the formula (1) ##STR15## wherein R 1 is a monovalent organic group containing an aromatic ring, R 2 is a divalent organic group containing a carbon atom which directly bonds to a silicone atom, m is an integer of 1 or 2, X is a hydrolyzable group selected from the group consisting of alkoxy, acetoxy, phenoxy and halogen, and Y is a group selected from the group consisting of alkyl, alkoxy, acetoxy, phenoxy, silyl, siloxy, disilanyl, organosilyl, organosiloxy, organohalosilyl and organohalosiloxy, through a secondary amino group (>NH) and at least one hydrolyzable group (X) in the above formula (1) to prepare a silane-modified polycarboxylic acid component represented by the formula (2) ##STR16## wherein T c1 is a monovalent residue of the organic tetracarboxylic acid component, T c2 is a divalent residue of the organic tetracarboxylic acid component, Z is an acid radical which may contain X bonded to carbonyl carbon, R 1 , R 2 , m, X and Y are the same as defined above, and n is an integer of 2 or 3 when Y is alkoxy, acetoxy or phenoxy and is 2 when Y is a group other than alkoxy, acetoxy and phenoxy, and then polymerizing the resulting silane-modified polycarboxylic acid component with the residual organic tetracarboxylic acid component and a diamine.
Claim 2
Dependent Claim
249 words
A process for producing a polyimide precursor by polymerizing an organic tetracarboxylic acid component and a diamine, which comprises reacting a portion of an organic tetracarboxylic acid component with an aminosilane compound represented by the formula (1) ##STR15## wherein R 1 is a monovalent organic group containing an aromatic ring, R 2 is a divalent organic group containing a carbon atom which directly bonds to a silicone atom, m is an integer of 1 or 2, X is a hydrolyzable group selected from the group consisting of alkoxy, acetoxy, phenoxy and halogen, and Y is a group selected from the group consisting of alkyl, alkoxy, acetoxy, phenoxy, silyl, siloxy, disilanyl, organosilyl, organosiloxy, organohalosilyl and organohalosiloxy, through a secondary amino group (>NH) and at least one hydrolyzable group (X) in the above formula (1) to prepare a silane-modified polycarboxylic acid component represented by the formula (2) ##STR16## wherein T c1 is a monovalent residue of the organic tetracarboxylic acid component, T c2 is a divalent residue of the organic tetracarboxylic acid component, Z is an acid radical which may contain X bonded to carbonyl carbon, R 1 , R 2 , m, X and Y are the same as defined above, and n is an integer of 2 or 3 when Y is alkoxy, acetoxy or phenoxy and is 2 when Y is a group other than alkoxy, acetoxy and phenoxy, and then polymerizing the resulting silane-modified polycarboxylic acid component with the residual organic tetracarboxylic acid component and a diamine.
Claim 3
Dependent Claim
17 words
A process as claimed in claim 1, wherein the organic tetracarboxylic acid is an aromatic tetracarboxylic dianhydride.
Claim 4
Dependent Claim
64 words
A process as claimed in claim 2, wherein the organic tetracarboxylic dianhydride is selected from the group consisting of pyromellitic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic acid dianhydride, 3,3',4,4'-biphenyltetracarboxylic acid dianhydride, 2,3,3',4'-biphenyltetracarboxylic acid dianhydride, 2,3,6,7-naphthalene-tetracarboxylic acid dianhydride, 1,2,5,6-naphthalenetetracarboxylic acid dianhydride, 1,4,5,8-naphthalenetetracarboxylic acid dianhydride, 2,2-bis(3,4-dicarboxyphenyl)-propane dianhydride, bis(3,4-dicarboxyphenyl)sulfone dianhydride, 3,4,9,10-perylenetetracarboxylic acid dianhydride, bis(3,4-dicarboxyphenyl)ether dianhydride, 2,2-bis(2,3-dicarboxyphenyl)propane dianhydride, 1,1-bis(2,3-dicarboxyphenyl)ethane dianhydride, 1,1-bis(3,4-dicarboxyphenyl)-ethane dianhydride, benzene-1,2,3,4-tetracarboxylic acid dianhydride, 2,3,6,7-anthracenetetracarboxylic acid dianhydride and 1,2,7,8-phenanthrenetetracarboxylic acid dianhydride.
Claim 5
Dependent Claim
19 words
A process as claimed in claim 1, wherein the aminosilane compound is selected from the group consisting of ##STR17##
Claim 6
Dependent Claim
34 words
A process as claimed in claim 1, wherein the amount of the organic tetracarboxylic acid used for reacting with the aminosilane compound is about 2 to 3 mols per mol of the aminosilane compound.
Claim 7
Dependent Claim
24 words
A process as claimed in claim 1, wherein the reaction is conducted at 30° C. or less in the presence of a polar solvent.
Claim 8
Dependent Claim
27 words
A process as claimed in claim 1, wherein the diamine is selected from the group consisting of an aromatic diamine, an aliphatic diamine and an alicyclic diamine.
Claim 9
Dependent Claim
53 words
A process as claimed in claim 7, wherein the aromatic diamine is selected from the group consisting of m-phenylene diamine, p-phenylene diamine, 4,4'-diaminodiphenyl methane, 4,4'-diaminodiphenyl ether, 2,2'-bis(4-aminophenyl) propane, 3,3'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl sulfide, benzidine, benzidine-3,3'-dicarboxylic acid, benzidine-3,3'-disulfonic acid, benzidine-3-monocarboxylic acid, benzidine-3-monosulfonic acid, 3,3'-dimethoxybenzidine, p-bis(4-aminophenyl) benzene, m-bis(4-aminophenoxy) benzene, m-xylene diamine and p-xylene diamine.
Claim 10
Dependent Claim
32 words
A process as claimed in claim 1, wherein the amount of the diamine is equivalent to the total amount of the silane-modified polycarboxylic acid component and the unmodified organic tetracarboxylic acid component.
Claim 11
Dependent Claim
53 words
A process as claimed in claim 1, wherein the silane-modified polycarboxylic acid component is used in an amount such that the amount of the aminosilane compound is 0.05 to 10 mol% per the total mols of all the starting materials of the aminosilane compound, organic tetracarboxylic acid, unmodified organic tetracarboxylic acid and diamine.
Claim 12
Dependent Claim
24 words
A process as claimed in claim 1, wherein the polymerization is conducted at 60° C. or less in the presence of an organic solvent.
Claim 13
Dependent Claim
24 words
A process as claimed in claim 11, wherein the organic solvent is selected from the group consisting of N-methyl-2-pyrrolidone, N,N'-dimethylacetamide, N,N'-dimethylformamide, N,N'-dimethylsulfoxide and hexamethylphosphoramide.
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) | 1988-02-12 | 1988-08-13 | 1989-02-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-02-12 | 1992-08-13 | 1993-02-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-02-12 | 1996-08-13 | 1997-02-12 | $7700.00 | Window Closed / Lapsed |