US4206106A
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Vinyl end-capped polyimide oligomers
Assignee: Chevron USA Inc
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Filing: 1979-04-05
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Granted: 1980-06-03
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Expires: 1999-04-05
Abstract
Abstract The products of the invention are vinyl end-capped oligomers which are prepared from 2,4-bis (p-aminobenzyl) aniline and a vinyl substituted aromatic monoamine, the principal component of which is the compound whose structure is shown in FIG. 3. The products are prepared from either of two (2) precursors. The first precursor is a compound whose structure is shown in FIG. 2 and which is prepared from 2,4-bis (p-aminobenzyl) aniline, a dianhydride of an aromatic tetracarboxylic acid such as 3,3'4,4'-benzophenonetetracarboxylic acid (BTDA) and a vinyl substituted aromatic monoamine, such as 3-aminophenyl-ethylene (APE). The second precursor is a complex amine salt having the structure shown in FIG. 6 and which is prepared from 2,4-bis-(p-aminobenzyl) aniline, a dialkyl ester of BTDA and APE.
Inventors
- 👤 William J. Heilman
- 👤 Daniel J. Hurley
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 12:44
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1003; C08G73/1007; C08G73/101
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
126 words
A product selected from the group consisting of: A. An end-capped polyimide oligomer whose principal component has the structure: ##STR10## where R has the structure: ##STR11## where X is ##STR12## or a bond; where R' is an aryl group; and where R" is an aryl group bearing a substituent having the structure: --CH═CH.sub.2 ; B. A first precursor of an end-capped polyimide oligomer of (A) whose principal component has the structure: ##STR13## where R, R', and R" are defined as above; C. A second precursor of an end-capped polyimide oligomer of (A) whose principal component has the structure: ##STR14## where R, R', and R" are as defined above, and where R"' is the alcohol moiety from which the diester of the aromatic tetracarboxylic acid was prepared.
Claim 2
Dependent Claim
126 words
A product selected from the group consisting of: A. An end-capped polyimide oligomer whose principal component has the structure: ##STR10## where R has the structure: ##STR11## where X is ##STR12## or a bond; where R' is an aryl group; and where R" is an aryl group bearing a substituent having the structure: --CH═CH.sub.2 ; B. A first precursor of an end-capped polyimide oligomer of (A) whose principal component has the structure: ##STR13## where R, R', and R" are defined as above; C. A second precursor of an end-capped polyimide oligomer of (A) whose principal component has the structure: ##STR14## where R, R', and R" are as defined above, and where R"' is the alcohol moiety from which the diester of the aromatic tetracarboxylic acid was prepared.
Claim 3
Dependent Claim
44 words
An end-capped polyimide oligomer whose principal component has the structure: ##STR15## where R has the structure: ##STR16## where X is ##STR17## or a bond; where R' is an aryl group; and where R" is an aryl group bearing a substituent having the structure: --CH═CH.sub.2.
Claim 4
Dependent Claim
44 words
An end-capped polyimide oligomer whose principal component has the structure: ##STR15## where R has the structure: ##STR16## where X is ##STR17## or a bond; where R' is an aryl group; and where R" is an aryl group bearing a substituent having the structure: --CH═CH.sub.2.
Claim 5
Dependent Claim
54 words
A precursor of an acetylene end-capped polyimide oligomer of claim 1, the principal component of said precursor having the structure: ##STR18## where R has the structure: ##STR19## where X is ##STR20## or a bond; where R' is an aryl group; and where R" is an aryl group bearing a substituent having the structure: --CH═CH.sub.2.
Claim 6
Dependent Claim
70 words
A precursor of an end-capped polyimide oligomer of claim 1, the principal component of said precursor having the structure: ##STR21## where R has the structure: ##STR22## where X is ##STR23## or a bond; where R' is an aryl group; where R" is an aryl group bearing a substituent having the structure: --CH═CH.sub.2 and where R"' is the alcohol moiety from which the diester of the aromatic tetracarboxylic acid was prepared.
Claim 7
Dependent Claim
16 words
A product of claim 1, 2, 3 or 4 in which R' has the structure: ##STR24##
Claim 8
Dependent Claim
16 words
A product of claim 1, 2, 3 or 4 in which R has the structure: ##STR25##
Claim 9
Dependent Claim
23 words
A product of claim 1, 2, 3 or 4 in which R has the structure: ##STR26## and where R' has the structure: ##STR27##
Claim 10
Dependent Claim
27 words
A product of claim 1, 2, 3 or 4 in which R has the structure: ##STR28## R' has the structure: ##STR29## and R" has the structure: ##STR30##
Claim 11
Dependent Claim
29 words
A coating and laminating varnish consisting essentially of a product of claim 3 dissolved in a solvent selected from the group consisting of N-methyl-2-pyrrolidone, cyclohexanone, diethyl carbonate, and gamma-butyrolactone.
Claim 12
Dependent Claim
56 words
A coating and laminating varnish consisting essentially of a product of claim 4 dissolved in a solvent having an atmospheric boiling point of less than about 150° C. and selected from the group consisting of lower alkanols containing up to about 5 carbon atoms, lower ethers containing up to about 6 carbon atoms, and mixtures thereof.
Claim 13
Dependent Claim
32 words
A product of claim 1, 2, 3, 4, 9, or 10 in which up to 50 mol % of the terminal --CH═CH 2 groups of R" is replaced with a hydrogen atom.
Claim 14
Dependent Claim
167 words
A process for preparing a product of claim 3 which consists essentially of: A. Dissolving at least 17 weight % of an aromatic tetracarboxylic acid dianhydride in a solvent at a temperature of at least 60° C., B. Maintaining a solution of step (A) containing substantially 1 molar portion of said aromatic tetracarboxylic acid dianhydride at a temperature in a range of about 30°-100° C. and adding substantially 0.33 molar portion of an aromatic triamine thereto, and C. Adding substantially 1.0 molar portion of a vinyl substituted aromatic monoamine to the product of step (B); said aromatic tetracarboxylic acid dianhydride having the formula: ##STR31## where R has the structure: ##STR32## where X is ##STR33## or a bond; said aromatic triamine having the formula: ##STR34## where R' is an aryl group; and said vinyl substituted aromatic monoamine having the formula: H.sub.2 N--R"--CH.tbd.CH.sub.2 where R" is an aryl group; and the solvent employed in step (A) is selected from the group consisting of N-methyl-2-pyrrolidone, cyclohexanone, diethyl carbonate, and gamma-butyrolactone.
Claim 15
Dependent Claim
168 words
A process for preparing a product of claim 3 which consists essentially of: A. Adding, with stirring, a solution containing substantially 0.33 molar portion of an aromatic triamine to a solution containing substantially 1.0 molar portion of a dialkyl ester of an aromatic tetracarboxylic acid, and B. Adding substantially 1.0 molar portion of a vinyl substituted aromatic monoamine to the solution of (A); the dialkyl ester of the aromatic tetracarboxylic acid employed in step (A) having the formula: ##STR35## where R has the structure: ##STR36## where X is ##STR37## or a bond; said aromatic triamine having the formula: ##STR38## where R' is an aryl group; and said vinyl substituted aromatic monoamine having the formula: H.sub.2 N--R"--CH═CH.sub.2 where R" is an aryl group; the solvent employed in Step (A) having an atmospheric boiling point of less than about 150° C. and is selected from the group consisting of lower alkanols containing up to about 5 carbon atoms, lower ethers containing up to about 6 carbon atoms, and mixtures thereof.
Claim 16
Dependent Claim
14 words
A process of claim 12 or 13 in which R' has the structure: ##STR39##
Claim 17
Dependent Claim
14 words
A process of claim 12 or 13 in which R has the structure: ##STR40##
Claim 18
Dependent Claim
21 words
A process of claim 12 or 13 in which R has the structure: ##STR41## and where R' has the structure: ##STR42##
Claim 19
Dependent Claim
27 words
A process of claim 12 or 13 in which R has the structure: ##STR43## and where R' has the structure: ##STR44## and R" has the structure: ##STR45##
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) | 1983-06-03 | 1983-12-03 | 1984-06-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-06-03 | 1987-12-03 | 1988-06-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-06-03 | 1991-12-03 | 1992-06-03 | $7700.00 | Window Closed / Lapsed |