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US3745149A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of polyimides from mixtures of monomeric diamines and esters of polycarboxylic acids

Assignee: National Aeronautics and Space Administration
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Filing: 1971-09-29
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Granted: 1973-07-10
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Expires: 1991-09-29
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Abstract

Abstract Polyimides having high thermal and oxidative stability are prepared by the reaction, with application of heat, of a mixture of monomers comprising (a) a dialkyl or tetraalkyl ester of an aromatic tetracarboxylic acid, (b) an aromatic diamine, and (c) a monoalkyl or dialkyl ester of a dicarboxylic acid wherein the ratio of a:b:c is n:(n+1):2, wherein n has a value of from 1 to 20. The mixture of monomers is prepared in a 30 to 70 percent by weight solution of an organic solvent, a substrate impregnated with the solution and heated at 50* to 205*C to remove said solvent and form a low molecular weight prepolymer, and thereafter heated at 275* to 350*C to cure to a high molecular weight polyimide. In a specific embodiment, graphite fiber is impregnated with a solution of 60 percent by weight of a mixture of 2,5-dicarbomethoxyterephthalic acid, methylenedianiline, and 5-norbornene-2,3-dicarboxylic acid monomethyl ester in dimethyl formamide, the impregnated fiber heated at 50* to 120*C to remove solvent, and thereafter heated at about 205*C to form imidized prepolymer and then at 315*C to form a high molecular weight thermally stable polyimide.

Inventors

  • 👤 T Serafini
  • 👤 P Delvigs
  • 👤 G Lightsey

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 09:32
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1003; C08G73/1007; C08G73/101

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 38 words
A composition of matter as claimed in claim 1 wherein said mixture is dissolved in an organic solvent which is inert to the reactant mixture and comprises from 30 percent to 70 percent by weight of the solution.
Claim 2
Dependent Claim 12 words
A composition of matter as claimed in claim 2 wherein R4 is
Claim 3
Dependent Claim 13 words
A composition of matter as claimed in claim 3 wherein R5 is methyl.
Claim 4
Dependent Claim 25 words
A composition of matter as claimed in claim 2 wherein a is solid 2,5-dicarbomethoxyterephthalic acid; b is 4,4''-methylenedianiline; and c is 5-norbornene-2,3-dicarboxylic acid monomethyl ester.
Claim 5
Dependent Claim 25 words
A composition of matter as claimed in claim 2 wherein a is 2, 5-dicarbomethoxyterephthalic acid; b is 4,4''-thiodianiline; and c is 5-norbornene-2,3-dicarboxylic acid monomethyl ester.
Claim 6
Dependent Claim 29 words
A composition of matter as claimed in claim 2 wherein a is 3, 3'' ,4,4''-benzophenonetetracarboxylic acid dimethyl ester; b is 4, 4''-methylenedianiline; and c is 5-Norbornene-2,3-dicarboxylic acid monomethyl ester.
Claim 7
Dependent Claim 19 words
A process for preparing polyimides which comprises reacting, by application of heat, a mixture of compounds of the formulas:
Claim 8
Dependent Claim 36 words
A process as claimed in claim 8 wherein the reaction products are heated to a temperature of from about 275*C to about 350*C to obtain polyimide polymers having an average molecular weight in excess of 10,000.
Claim 9
Dependent Claim 32 words
A process for preparing polyimides which comprises heating a solution of solvent and from about 30 percent to about 70 percent by weight of a mixture of compounds of the following formulas:
Claim 10
Dependent Claim 38 words
A process as claimed in claim 10 including an additional heating step wherein said prepolymers are heated at temperatures of from about 275*C to 350*C to obtain polyimide polymers having an average molecular weight in excess of 10,000.

References Cited (Backward Citations)

US3647529A Cited
US3575924A Cited
US3632428A Cited
US3576691A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1976-07-09 1977-01-08 1977-07-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1980-07-09 1981-01-08 1981-07-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1984-07-09 1985-01-08 1985-07-10 $7700.00 Window Closed / Lapsed

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