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US4421905A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing polyimides end-capped with anhydride or isocyanate groups

Assignee: Plastics Engineering Co
•
Filing: 1982-09-20
•
Granted: 1983-12-20
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Expires: 2002-09-20
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Abstract

Abstract The process described herein comprises the preparation of polyimides by the reaction of aromatic dianhydrides and aromatic diisocyanates in the presence of a metal acetylacetonate, such as Al, Co, Fe, Ni, Zr, etc. By using appropriate proportions, the polyimides may be end-capped with either anhydride or isocyanate groups. The use of the acetylacetonate permits the use of lower temperatures for imide ring closure thereby avoiding undesirable coreaction between anhydride groups and certain solvents. "Polyimide dianhydride" is an anhydride-terminated polyimide; and "polyimide diisocyanate" is an isocyanate-terminated polyimide as represented by the respective formulas: ##STR1## wherein Ar', Ar and n are as defined hereinafter. By this process, the polyimide dianhydride product has an anhydride activity of at least 0.17 as defined herein regardless of the type of solvent used.

Inventors

  • 👤 Chung J. Lee

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 12:27
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1003; C08G73/1035; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/34; C08G18/343; C08G18/346; C08G73/1067

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 207 words
In the process of preparing a polyimide of the formula: ##STR13## by the reaction of an aromatic dianhydride of the formula: ##STR14## with an aromatic diisocyanate of the formula OCN--Ar--CNO; wherein Ar' is a tetravalent aromatic organic radical, the four carbonyl groups being attached directly to separate carbon atoms and each pair of carbonyl groups being attached to adjacent carbon atoms in the Ar' radical except that in the case of the Ar' being a naphthalene radical one or both pairs of the carbonyl groups may be attached to peri carbon atoms; Ar is a divalent aromatic radical; n is an integer of at least one; D is a radical selected from the group consisting of O< and >N--AR--NCO; and D' is a radical selected from the group consisting of OC< and ##STR15## the improvement comprising the reaction of said aromatic dianhydride and said aromatic diisocyanate while in intimate contact with each other and with a metal acetylacetonate in which said metal is selected from the class consisting of Al, Co, Fe, Ni and Zr, the temperature of said reaction being in the range of 70°-150° C. and the amount of said metal acetylacetonate being in the range of 0.005-1 gram per equivalent weight of aromatic dianhydride.
Claim 2
Dependent Claim 207 words
In the process of preparing a polyimide of the formula: ##STR13## by the reaction of an aromatic dianhydride of the formula: ##STR14## with an aromatic diisocyanate of the formula OCN--Ar--CNO; wherein Ar' is a tetravalent aromatic organic radical, the four carbonyl groups being attached directly to separate carbon atoms and each pair of carbonyl groups being attached to adjacent carbon atoms in the Ar' radical except that in the case of the Ar' being a naphthalene radical one or both pairs of the carbonyl groups may be attached to peri carbon atoms; Ar is a divalent aromatic radical; n is an integer of at least one; D is a radical selected from the group consisting of O< and >N--AR--NCO; and D' is a radical selected from the group consisting of OC< and ##STR15## the improvement comprising the reaction of said aromatic dianhydride and said aromatic diisocyanate while in intimate contact with each other and with a metal acetylacetonate in which said metal is selected from the class consisting of Al, Co, Fe, Ni and Zr, the temperature of said reaction being in the range of 70°-150° C. and the amount of said metal acetylacetonate being in the range of 0.005-1 gram per equivalent weight of aromatic dianhydride.
Claim 3
Dependent Claim 27 words
The process of claim 1 in which a polyimide dianhydride is produced by using n+1 moles of said aromatic dianhydride and n moles of said aromatic diisocyanate.
Claim 4
Dependent Claim 25 words
The process of claim 2 in which a polyimide dianhydride is produced having an anhydride activity greater than 0.17 as measured by its infrared spectrum.
Claim 5
Dependent Claim 25 words
The process of claim 3 in which the amount of said metal acetyl acetonate is in the range of 0.01-0.05 gram per said equivalent weight.
Claim 6
Dependent Claim 23 words
The process of claim 3 in which said reaction is conducted at a temperature in the range of 100° C. to 140° C.
Claim 7
Dependent Claim 13 words
The process of claim 5 in which said metal acetylacetonate is Al acetylacetonate.
Claim 8
Dependent Claim 13 words
The process of claim 5 in which said metal acetylacetonate is Co acetylacetonate.
Claim 9
Dependent Claim 13 words
The process of claim 5 in which said metal acetylacetonate is Ni acetylacetonate.
Claim 10
Dependent Claim 13 words
The process of claim 5 in which said metal acetylacetonate is Fe acetylacetonate.
Claim 11
Dependent Claim 13 words
The process of claim 5 in which said metal acetylacetonate is Zr acetylacetonate.
Claim 12
Dependent Claim 13 words
The process of claim 3 in which said aromatic dianhydride is 3,4,3',4'-benzophenonetetracarboxylic dianhydride.
Claim 13
Dependent Claim 14 words
The process of claim 11 in which said aromatic diisocyanate is a toluene diisocyanate.
Claim 14
Dependent Claim 14 words
The process of claim 1 in which said aromatic diisocyanate is a toluene diisocyanate.

References Cited (Backward Citations)

US3682860A Cited
US3997513A Cited
US4094864A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-12-19 1987-06-20 1987-12-20 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-12-19 1991-06-20 1991-12-20 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-12-19 1995-06-20 1995-12-20 $7700.00 Window Closed / Lapsed

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