US3931354A
Expired / Lapsed
US
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Reaction products of carboxyl terminated 1,2-polybutadiene with epoxides and aromatic bis(maleimides)
Assignee: Northrop Grumman Space and Mission Systems Corp
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Filing: 1974-08-26
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Granted: 1976-01-06
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Expires: 1994-08-26
Abstract
Abstract A functionally terminated polybutadiene polymer is reacted with an epoxide to produce an epoxide terminated polybutadiene. A crosslinking agent and a peroxide free radical initiator are mixed with the epoxy terminated polybutadiene, and upon reaction, a thermoset resin is produced having advanced chemical, electrical, and thermomechanical properties.
Inventors
- 👤 Clyde H. Sheppard
- 👤 Robert J. Jones
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 20:18
CPC Classifications
C; C08; C08L; C08L13/00; C08C; C08C19/00; C08C19/30; C08C19/34; C08C19/40; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014; C08G59/4042; C08G59/42; C08G59/4284; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/35; C08L63/00; C08K5/04; C08K5/14; C08L63/04; Y; Y10; Y10T; Y10T428/00; Y10T428/29; Y10T428/2913; Y10T428/2916; Y10T428/2918; Y10T428/2933; Y10T428/2964; Y10T428/2967
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
74 words
A hard thermoset resin which is a reaction product of the ratio of: 1. one mole of 1,2-polybutadiene having at least two carboxyl terminal groups; 2. two moles of an epoxide selected from the group consisting of alkylene epoxide, cycloalkylene epoxide, alkoxyarylene epoxide, arylene epoxide, alkyl cycloalkylene epoxide, cycloalkene epoxide, and alkylenecycloalkylene epoxide; 3. 0.1 to 0.8 moles of an aromatic amine maleimide per mole of 1,2-polybutadiene; and 4. a peroxide free radical initiator.
Claim 2
Dependent Claim
74 words
A hard thermoset resin which is a reaction product of the ratio of: 1. one mole of 1,2-polybutadiene having at least two carboxyl terminal groups; 2. two moles of an epoxide selected from the group consisting of alkylene epoxide, cycloalkylene epoxide, alkoxyarylene epoxide, arylene epoxide, alkyl cycloalkylene epoxide, cycloalkene epoxide, and alkylenecycloalkylene epoxide; 3. 0.1 to 0.8 moles of an aromatic amine maleimide per mole of 1,2-polybutadiene; and 4. a peroxide free radical initiator.
Claim 3
Dependent Claim
29 words
A hard thermoset resin according to claim 1 wherein: said maleimide is selected from the group consisting of methylene dianiline maleimide, thiodianiline, meta-phenylene diamine maleimide, maleimide, and oxydianiline maleimide.
Claim 4
Dependent Claim
78 words
A thermosetting polymer comprising a reaction product of the ratio of: 1. one mole of 1,2-polybutadiene having at least two carboxyl terminal groups; 2. two moles of an expoxide selected from the group consisting of alkylene epoxide, cycloalkylene epoxide, alkoxyarylene epoxide, arylene epoxide, alkyl cycloalkylene epoxide, cycloalkene epoxide, and alkylenecycloalkylene epoxide; 3. 0.1 to 0.8 moles of an aromatic amine maleimide per mole of 1,2-polybutadiene; and 4. a peroxide free radical initiator homogeneously dispersed throughout the reaction product.
Claim 5
Dependent Claim
78 words
A thermosetting polymer comprising a reaction product of the ratio of: 1. one mole of 1,2-polybutadiene having at least two carboxyl terminal groups; 2. two moles of an expoxide selected from the group consisting of alkylene epoxide, cycloalkylene epoxide, alkoxyarylene epoxide, arylene epoxide, alkyl cycloalkylene epoxide, cycloalkene epoxide, and alkylenecycloalkylene epoxide; 3. 0.1 to 0.8 moles of an aromatic amine maleimide per mole of 1,2-polybutadiene; and 4. a peroxide free radical initiator homogeneously dispersed throughout the reaction product.
Claim 6
Dependent Claim
32 words
A thermosetting polymer according to claim 3 wherein: said epoxide is selected from the group consisting of alkylene epoxide, cycloalkylene epoxide, alkoxyarylene alkylcycloalkylene arylene epoxide, alkycycloalkylene epoxide, cycloalkene epoxide, and alkenecycloalkylene epoxide.
Claim 7
Dependent Claim
28 words
A thermosetting polymer according to claim 3 wherein: said maleimide is selected from the group consisting of methylene dianiline maleimide, thiodianiline maleimide, meta-phenylene diamine maleimide, and oxydianiline maleimide.
Claim 8
Independent Claim
79 words
A method of producing a hard thermoset polybutadiene-epoxy resin comprising: A. reacting by ratio (1) one mole of 1,2-polybutadiene having at least two carboxyl terminal groups with (2) two moles of an epoxide to form an epoxy end-capped polybutadiene; B. mixing the epoxy end-capped polybutadiene terminated adduct with (3) a peroxide free radical initiator and (4) 0.1 to 0.8 moles of an aromatic amine maleimide per mole of 1,2-polybutadiene; and C. curing the mixture to a hard thermoset resin.
Claim 9
Independent Claim
79 words
A method of producing a hard thermoset polybutadiene-epoxy resin comprising: A. reacting by ratio (1) one mole of 1,2-polybutadiene having at least two carboxyl terminal groups with (2) two moles of an epoxide to form an epoxy end-capped polybutadiene; B. mixing the epoxy end-capped polybutadiene terminated adduct with (3) a peroxide free radical initiator and (4) 0.1 to 0.8 moles of an aromatic amine maleimide per mole of 1,2-polybutadiene; and C. curing the mixture to a hard thermoset resin.
Claim 10
Dependent Claim
31 words
A method according to claim 6 wherein: said epoxide is selected from the group consisting of alkylene epoxide, cycloalkylene epoxide, alkoxyarylene epoxide, arylene epoxide, alkylcycloalkylene epoxide, cycloalkene epoxide, and alkenecycloalkylene epoxide.
Claim 11
Dependent Claim
24 words
A method according to claim 6 wherein: said maleimide is selected from the group consisting of methylene dianiline maleimide, thiodianiline maleimide, and oxydianiline maleimide.
Claim 12
Dependent Claim
88 words
A method according to claim 6 wherein: the two dicarboxyl terminated groups are formed by the reaction of one equivalent of dihydroxy-1,2-polybutadiene with one equivalent of an acid anhydride and is selected from the group consisting of trimellitic anhydride; tetrahydrophthalic anhydride; hexahydrophthalic anhydride; tetrachlorophthalic anhydride, tetrabromophthalic anhydride; chlorendic anhydride; nadic anhydride; maleic anhydride; oxalic anhydride; succinic anhydride; malonic anhydride; suberic anhydride; azelaic anhydride; sebacic anhydride; adipic anhydride; glutaric anhydride; pimelic anhydride; phthalic anhydride; 3,4',4,4'-benzophenone tetracarboxylic dianhydride; polyazelaic polyanhydride, pyromellitic dianhydride; 1,2,3,4,-cyclopentane tetracarboxylic dianhydride; and endo-cis bicyclo (2.2.1)-5-heptene-2,3-dicarboxylic dianhydride.
References Cited (Backward Citations)
US3515772A
Cited
US3855176A
Cited
US3730948A
Cited
US3853815A
Cited
US3673274A
Cited
US3738967A
Cited
US3763087A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-05 | 1979-07-07 | 1980-01-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-05 | 1983-07-07 | 1984-01-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-05 | 1987-07-07 | 1988-01-06 | $7700.00 | Window Closed / Lapsed |