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US4251420A Expired / Lapsed US ⏱️ 0.0 years remaining

End-capped polyimide oligomers

Assignee: Chevron USA Inc
•
Filing: 1979-04-23
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Granted: 1981-02-17
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Expires: 1999-04-23
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Abstract

Abstract The products of the invention are end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic acid such as 3,3'4,4'-benzophenonetetracarboxylic acid, an aromatic triamine, and a 1-(aminoaryl)-3-hydroxy-3-methyl-1-butyne. The structure of the polyimide oligomers is shown in FIG. 3.

Inventors

  • 👤 Patricia A. Antonoplos
  • 👤 William J. Heilman

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 14:50
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1003; C08G73/1007; C08G73/101

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 129 words
A product selected from the group consisting of: A. An acetylene 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; ##STR13## B. A first precursor of an acetylene end-capped polyimide oligomer of (A) whose principal component has the structure; ##STR14## where R, R' and R" are as defined above; and C. A second precursor of an acetylene end-capped polyimide oligomer of (A) whose principal component has the structure; ##STR15## 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 129 words
A product selected from the group consisting of: A. An acetylene 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; ##STR13## B. A first precursor of an acetylene end-capped polyimide oligomer of (A) whose principal component has the structure; ##STR14## where R, R' and R" are as defined above; and C. A second precursor of an acetylene end-capped polyimide oligomer of (A) whose principal component has the structure; ##STR15## 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 45 words
An acetylene end-capped polyimide oligomer whose principal component has the structure; ##STR16## where R has the structure; ##STR17## where X is ##STR18## or a bond; where R' is an aryl group, and where R" is an aryl group bearing a substituent having the structure: ##STR19##
Claim 4
Dependent Claim 45 words
An acetylene end-capped polyimide oligomer whose principal component has the structure; ##STR16## where R has the structure; ##STR17## where X is ##STR18## or a bond; where R' is an aryl group, and where R" is an aryl group bearing a substituent having the structure: ##STR19##
Claim 5
Dependent Claim 47 words
A precursor of an acetylene end-capped polyimide oligomer, said precursor having the structure: ##STR20## where R has the structure; ##STR21## where X is ##STR22## or a bond; where R' is an aryl group; and where R" is an aryl group bearing a substituent having the structure: ##STR23##
Claim 6
Dependent Claim 47 words
A precursor of an acetylene end-capped polyimide oligomer, said precursor having the structure: ##STR20## where R has the structure; ##STR21## where X is ##STR22## or a bond; where R' is an aryl group; and where R" is an aryl group bearing a substituent having the structure: ##STR23##
Claim 7
Dependent Claim 64 words
A precursor of an acetylene end-capped polyimide oligomer, said precursor having the structure: ##STR24## where R has the structure; ##STR25## where X is ##STR26## or a bond; where R' is an aryl group; where R" is an aryl group bearing a substituent having the structure: ##STR27## and where R''' is the alcohol moiety from which the diester of the aromatic tetracarboxylic acid was prepared.
Claim 8
Dependent Claim 64 words
A precursor of an acetylene end-capped polyimide oligomer, said precursor having the structure: ##STR24## where R has the structure; ##STR25## where X is ##STR26## or a bond; where R' is an aryl group; where R" is an aryl group bearing a substituent having the structure: ##STR27## and where R''' is the alcohol moiety from which the diester of the aromatic tetracarboxylic acid was prepared.
Claim 9
Dependent Claim 16 words
A product of claim 1, 2, 3, or 4 in which R' has the structure: ##STR28##
Claim 10
Dependent Claim 15 words
A product of claim 1, 2, 3, 4 in which R has the structure: ##STR29##
Claim 11
Dependent Claim 23 words
A product of claim 1, 2, 3, or 4 in which R has the structure: ##STR30## and where R' has the structure: ##STR31##
Claim 12
Dependent Claim 27 words
A product of claim 1, 2, 3, or 4 in which R has the structure: ##STR32## R' has the structure: ##STR33## and R" has the structure: ##STR34##
Claim 13
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 14
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 15
Dependent Claim 31 words
A product of claim 1, 2, 3, 4, 9, or 10 in which up to 50 mol % of the terminal ##STR35## groups of R" is replaced with a hydrogen atom.
Claim 16
Dependent Claim 160 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 1-(aminoaryl)-3-hydroxy-3-methyl-1-butyne to the product of step (b); said aromatic tetracarboxylic acid dianhydride having the formula: ##STR36## where R has the structure: ##STR37## where X is ##STR38## or a bond; said aromatic triamine having the formula: ##STR39## where R' is an aryl group; and said 1-(aminoaryl)-3-hydroxyl-3-methyl-1-butyne having the formula: ##STR40## 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 17
Dependent Claim 177 words
A process for preparing a product of claim 4 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 1-(aminoaryl)-3-hydroxy-3-methyl-1-butyne to the solution of (A); the dialkyl ester of the aromatic tetracarboxylic acid employed in step (A) having the formula: ##STR41## where R has the structure: ##STR42## where X is ##STR43## or a bond, and where R''' is the moiety of an alkanol containing up to about 5 carbon atoms; said aromatic triamine having the formula: ##STR44## where R' is an aryl group; and said 1-(aminoaryl)-3-hydroxyl-3-methyl-1-butyne having the formula: ##STR45## 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 18
Dependent Claim 14 words
A process of claim 12 or 13 in which R' has the structure: ##STR46##
Claim 19
Dependent Claim 14 words
A process of claim 12 or 13 in which R has the structure: ##STR47##
Claim 20
Dependent Claim 21 words
A process of claim 12 or 13 in which R has the structure: ##STR48## and where R' has the structure: ##STR49##
Claim 21
Dependent Claim 25 words
A process of claim 12 or 13 in which R has the structure: ##STR50## R' has the structure: ##STR51## and R" has the structure: ##STR52##
Claim 22
Dependent Claim 38 words
A process for preparing a product of claim 2 which consists essentially of preparing a product of claim 3 by the method of claim 9 and effecting ring closure of the amic acid groups by a dehydration reaction.
Claim 23
Dependent Claim 38 words
A process for preparing a product of claim 2 which consists essentially of preparing a product of claim 4 by the process of claim 10 and heating said product to effect a ring closure to form imide groups.
Claim 24
Dependent Claim 29 words
A process of claim 12, 13, 18 or 19 in which up to 50 mol % of the terminal ##STR53## groups of R" is replaced with a hydrogen atom.

References Cited (Backward Citations)

US3845018A Cited
US3998786A Cited
US4058505A Cited
US3879349A Cited
US3864309A Cited
US4098767A Cited
US4100138A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-02-17 1984-08-18 1985-02-17 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-02-17 1988-08-18 1989-02-17 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-02-17 1992-08-18 1993-02-17 $7700.00 Window Closed / Lapsed

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