US5025089A
Expired / Lapsed
US
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Copolyimides derived from 2,2-bis (amino phenyl) hexafluoropropane
Assignee: CNA Holdings LLC
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Filing: 1989-11-13
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Granted: 1991-06-18
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Expires: 2009-11-13
Abstract
Abstract Copolyimides derived from the reaction product of 3,3'-6 F diamine or 4,4'-6 F diamine, at least one other diamine, and pyromellitic dianhydride can be rendered solvent soluble while at the same time exhibiting an improvement in both mechanical and electrical properties by the inclusion of at least one other dianhydride having a diaryl nucleus in the reaction media. Suitable such dianhydrides include bis (3,4 dicarboxy phenyl) ether dianhydride, 3,3'4,4' benzophenone tetracarboxylic dianhydride, 3,3',4,4' diphenyl tetracarboxylic acid dianhydride and 2,2 bis(3,4 dicarboxyphenyl) hexafluoropropane dianhydride (6F-DA). Such polyimides are soluble in common organic solvents such as methyl ethyl ketone or N-methyl pyrrolidone, and exhibit excellent film forming properties with improved mechanical and electrical properties as compared to the corresponding homopolyimides. They possess excellent heat stability (Tg's in excess of about 350° C.) and have superior electrical properties, for example, dielectric constant of less than about 2.5 at 10 megahertz.
Inventors
- 👤 Rohitkumar H. Vora
- 👤 Paul N. Chen, Sr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 15:43
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1042
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
158 words
A polyimide polymer soluble in N-methylpyrrolidone comprising the imidized condensation product of a mixture of diamines comprising: (a) a diamine selected from the group consisting of 2, 2-bis(3-aminophenyl) hexafluouropropane and 2,2-bis(4-aminophenyl) hexafluoropropane; (b) a second diamine having the formula H 2 N--R--NH 2 wherein R is a divalent aromatic radical comprising a phenylene, napthalene or bis-phenlene group; and a mixture of dianhydrides comprising: (c) pyromellitic dianhydride; and (d) at least one additional dianhydride selected from the groups consisting of bis (3,4-dicarboxyphenyl) ether dianhydride, 3,3', 4,4' benzophenone tetracarboxylic dianhydride, 3,3', 4,4' diphenyl tetracarboxylic acid dianhydride and 2,2 bis (3,4 dicarboxy phenyl) hexafluoropropane dianhydride, the relative proportions of said dianhydrides present in the mixture being from about 35 to about 75 mole percent of (c) and from about 25 to about 65 mole percent of (d), and the relative molar proportion of said diamine (a) and said diamine (b) being in the range of from about 3:1 to 1:3 respectively.
Claim 2
Dependent Claim
158 words
A polyimide polymer soluble in N-methylpyrrolidone comprising the imidized condensation product of a mixture of diamines comprising: (a) a diamine selected from the group consisting of 2, 2-bis(3-aminophenyl) hexafluouropropane and 2,2-bis(4-aminophenyl) hexafluoropropane; (b) a second diamine having the formula H 2 N--R--NH 2 wherein R is a divalent aromatic radical comprising a phenylene, napthalene or bis-phenlene group; and a mixture of dianhydrides comprising: (c) pyromellitic dianhydride; and (d) at least one additional dianhydride selected from the groups consisting of bis (3,4-dicarboxyphenyl) ether dianhydride, 3,3', 4,4' benzophenone tetracarboxylic dianhydride, 3,3', 4,4' diphenyl tetracarboxylic acid dianhydride and 2,2 bis (3,4 dicarboxy phenyl) hexafluoropropane dianhydride, the relative proportions of said dianhydrides present in the mixture being from about 35 to about 75 mole percent of (c) and from about 25 to about 65 mole percent of (d), and the relative molar proportion of said diamine (a) and said diamine (b) being in the range of from about 3:1 to 1:3 respectively.
Claim 3
Dependent Claim
16 words
The polyimide of claim 1 having a glass transition temperature of at least about 350° C.
Claim 4
Dependent Claim
22 words
The polyimide of claim 1 having a weight loss at 343° C. after 235 hours of not greater than about 3.0 percent.
Claim 5
Dependent Claim
22 words
The polyimide of claim 1 wherein said mixture of dianhydrides are present at a ratio of about 50 mole percent of each.
Claim 6
Dependent Claim
80 words
The polyimide of claim 1 wherein said second diamine (b) has the formula: ##STR2## wherein R' is selected from the group consisting of a C 1 to C 4 alkylene group, such as methylene, ethylene, propylene, and isopropylene; a covalent carbon to carbon bond; 1-phenyl-2,2,2-trifluoroethylidene; dichloro and difluoroalkylenes up to 3 carbons; oxy; thio; sulfinyl; sulfonyl; sulfonamido; carbonyl; oxydi carbonyl; oxydimethylene; sulfonyldioxy; carbonyldioxy; disilanylene; polysilanylene having up to 8 Si atoms; disiloxanylene; and a polysiloxanylene up to 8 Si atoms.
Claim 7
Dependent Claim
25 words
The polyimide of claim 5 wherein R' is selected from the group consisting of oxy, carbonyl, methylene, a covalent carbon to carbon bond, and sulfonyl.
Claim 8
Dependent Claim
9 words
The polyimide of claim 6 wherein R' is oxy.
Claim 9
Dependent Claim
22 words
The polyimide of claim 1 wherein said mixture of diamines are present at a ratio of about 50 mole percent of each.
Claim 10
Dependent Claim
14 words
The polyimide of claim 1 wherein said diamine (a) is 2,2 bis (4-aminophenyl) hexafluoropropane.
Claim 11
Dependent Claim
16 words
The polyimide of claim 9 wherein said additional dianhydride is 2,2 bis (3,4 dicarboxyphenyl) hexafluoropropane dianhydride.
Claim 12
Dependent Claim
22 words
The polyimide of claim 10 wherein said mixture of dianhydrides are present at a ratio of about 50 mole percent of each.
Claim 13
Dependent Claim
16 words
The polyimide of claim 1 having a glass transition temperature of at least about 350° C.
Claim 14
Dependent Claim
17 words
The polyimide of claim 1 having a dielectric constant of less than about 2.5 at 10 megahertz.
Claim 15
Dependent Claim
11 words
A solution of the polyimide of claim 1 in organic solvent.
Claim 16
Dependent Claim
19 words
A film prepared by coating the solution of claim 14 on a suitable substrate, and evaporating off the solvent.
Claim 17
Dependent Claim
9 words
A fiber prepared from the copolyimide of claim 1.
Claim 18
Dependent Claim
12 words
A composite comprising the polyimide of claim 1 mixed with reinforcing fibers.
References Cited (Backward Citations)
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| 3.5 Years (Year 4) | 1994-06-17 | 1994-12-17 | 1995-06-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-06-17 | 1998-12-17 | 1999-06-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-06-17 | 2002-12-17 | 2003-06-18 | $7700.00 | Window Closed / Lapsed |