Patent US3853815A successfully refreshed from Google Patents.
US3853815A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Thermosetting cyclized polydiene resins
Assignee: Northrop Grumman Space and Mission Systems Corp
•
Filing: 1973-05-02
•
Granted: 1974-12-10
•
Expires: 1993-05-02
Abstract
Abstract A hydroxy, amino, or mercapto terminated polydiene polymer is reacted with an organic acid anhydride to produce a carboxylic acid terminated polydiene. An organic chain extender and a peroxide free radical initiator is mixed with the polydiene, and upon reaction, an elastomeric material having the peroxide homogeneously dispersed therethrough substantially unreacted is formed. When the temperature is raised, the peroxide in the elastomer effects a cure to produce a hard thermoset resin.
Inventors
- 👤 H Lubowitz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 21:41
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/68; C08G63/682; C08G63/6824; C08G63/6828; C08C; C08C19/00; C08C19/30; C08C19/34; C08C19/36; C08G63/02; C08G63/12; C08G63/52; C08G63/54; C08G63/553; C08G63/56; C08G63/58
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
101 words
A HARD THERMOSET RESIN WHICH IS A REACTION PRODUCT OF THE RATIO OF (1) ONE EQUIVALENT OF A POLYDIENE HAVING (I) POLYFUNCTIONAL GROUPS SELECTED FROM THE GROUP CONSISTING OF HYDROXYL, AMINO, AND MERCAPTO, AND (II) A PREDOMINANT AMOUNT OF PENDANT VINYL GROUPS ON ALTERNATE CARBON ATOMS OF THE POLYDIENE BACKBONE; (2) ONE GRAM MOLE OF A CARBOXYLIC ACID ADDUCT FORMING ALIPHATIC OR AROMATIC ACID ANHYDRIDE CAPABLE OF REACTING WITH THE POLYFUNCTIONAL GROUPS OF THE POLYDIENE; (3) ONE EQUIVALENT OF A POLYFUNCTIONAL ALIPHATIC OR AROMATIC CHAIN EXTENDER CAPABLE OF REACTING WITH THE CARBOXYLIC ACID ADDUCT; AND (4) A PEROXIDE FREE RADICAL INITIATOR.
Claim 2
Dependent Claim
101 words
A HARD THERMOSET RESIN WHICH IS A REACTION PRODUCT OF THE RATIO OF (1) ONE EQUIVALENT OF A POLYDIENE HAVING (I) POLYFUNCTIONAL GROUPS SELECTED FROM THE GROUP CONSISTING OF HYDROXYL, AMINO, AND MERCAPTO, AND (II) A PREDOMINANT AMOUNT OF PENDANT VINYL GROUPS ON ALTERNATE CARBON ATOMS OF THE POLYDIENE BACKBONE; (2) ONE GRAM MOLE OF A CARBOXYLIC ACID ADDUCT FORMING ALIPHATIC OR AROMATIC ACID ANHYDRIDE CAPABLE OF REACTING WITH THE POLYFUNCTIONAL GROUPS OF THE POLYDIENE; (3) ONE EQUIVALENT OF A POLYFUNCTIONAL ALIPHATIC OR AROMATIC CHAIN EXTENDER CAPABLE OF REACTING WITH THE CARBOXYLIC ACID ADDUCT; AND (4) A PEROXIDE FREE RADICAL INITIATOR.
Claim 3
Dependent Claim
21 words
A hard thermoset resin according to claim 1 wherein the polydiene is selected from the group consisting of 1,2-polybutadiene and 3,4-polyisoprene.
Claim 4
Dependent Claim
52 words
A hard thermoset resin according to claim 1 wherein the acid anhydride is selected from the group consisting of trimellitic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic 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 and phthalic anhydride.
Claim 5
Dependent Claim
58 words
A hard thermoset resin according to claim 1 wherein said chain extender is selected from the group consisting of alkylene diepoxide, cycloalkylene diepoxide, alkoxyarylene diepoxide, arylene diepoxide, alkylcycloalkylene diepoxide, cycloalkene diepoxide, alkenecycloalkylene diepoxide, alkylene diimine, arylene diimine, alkarylene diimine, arylene diamine, arylalkylenimide, alkylenimine alkarylene diamine, oxyarylene diamine, cycloalkylene diol, cycloalkylalkylene diol, aralkylene diol, alkylene diol, and arylene diol.
Claim 6
Dependent Claim
34 words
A hard thermoset resin according to claim 1 wherein the acid anhydride is selected from the group consisting of 3,3'',4,4''-benzophenone tetracarboxylic dianhydride, polyazelaic polyanhydride, pyromellitic dianhydride, 1,2,3,4-cyclopentane tetracarboxylic dianhydride, and endo-cis bicyclo (2.2.1.)-5-heptane-2,3-dicarboxylic dianhydride.
Claim 7
Dependent Claim
106 words
A thermosetting elastomeric polymer comprising a reaction product of the ratio of (1) one equivalent of a polydiene having (i) polyfunctional groups selected from the group consisting of hydroxyl, amino, and mercapto and (ii) a predominant amount of pendant vinyl groups on alternate carbon atoms of the polydiene backbone; (2) one gram mole of a carboxylic acid adduct forming aliphatic or aromatic acid anhydride capable of reacting with the polyfunctional groups of the polydiene; (3) one equivalent of a polyfunctional aliphatic or aromatic chain extender capable of reacting with the carboxylic acid adduct; and (4) a peroxide free radical initiator homogeneously dispersed throughout the reaction product.
Claim 8
Dependent Claim
106 words
A thermosetting elastomeric polymer comprising a reaction product of the ratio of (1) one equivalent of a polydiene having (i) polyfunctional groups selected from the group consisting of hydroxyl, amino, and mercapto and (ii) a predominant amount of pendant vinyl groups on alternate carbon atoms of the polydiene backbone; (2) one gram mole of a carboxylic acid adduct forming aliphatic or aromatic acid anhydride capable of reacting with the polyfunctional groups of the polydiene; (3) one equivalent of a polyfunctional aliphatic or aromatic chain extender capable of reacting with the carboxylic acid adduct; and (4) a peroxide free radical initiator homogeneously dispersed throughout the reaction product.
Claim 9
Dependent Claim
22 words
A thermosetting elastomeric polymer according to claim 6 wherein the polydiene is selected from the group consisting of 1, 2-polybutadiene and 3,4-polyisoprene.
Claim 10
Dependent Claim
56 words
A thermosetting elastomeric polymer according to claim 6 wherein the acid anhydride 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, and phthalic anhydride.
Claim 11
Dependent Claim
58 words
A thermosetting elastomeric polymer according to claim 6 wherein said chain extender is selected from the group consisting of alkylene diepoxide; cycloalkylene diepoxide; alkoxyarylene diepoxide; arylene diepoxide; alkylcycloalkylene diepoxide; cycloalkene diepoxide; alkenecycloalkylene diepoxide; alkylene diimine; arylene diimine; alkarylene diimine; arylene diamine; arylalkylenimine; alkylenimine alkarylene diamine; oxyarylene diamine; cycloalkylene diol; cycloalkylalkylene diol; aralkylene diol; alkylene diol; and arylene diol.
Claim 12
Dependent Claim
34 words
A thermosetting elastomeric polymer according to claim 6 wherein the acid anhydride is selected from the group consisting of 3,3'',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.
Claim 13
Independent Claim
146 words
A method of producing a hard thermoset polydiene resin comprising: A. reacting by ratio (1) one equivalent of a polydiene having (i) polyfunctional groups selected from the group consisting of hydroxyl, amino, and mercapto and (ii) a predominant amount of pendant vinyl groups on alternate carbon atoms of the polydiene backbone with (2) one gram mole of an aliphatic or aromatic acid anhydride capable of reacting with the polyfunctional groups of the polydiene to form a carboxylic acid terminated adduct; B. mixing the polydiene carboxylic acid terminated adduct with (3) a peroxide free radical initiator and (4) one equivalent of an aliphatic or aromatic chain extender capable of reacting with the adduct; C. reacting the adduct and the chain extender to form an elastomeric polymeric material having the peroxide initiator homogeneously dispersed therethrough substantially unreacted; and D. subsequently curing the elastomer to a hard thermoset resin.
Claim 14
Independent Claim
146 words
A method of producing a hard thermoset polydiene resin comprising: A. reacting by ratio (1) one equivalent of a polydiene having (i) polyfunctional groups selected from the group consisting of hydroxyl, amino, and mercapto and (ii) a predominant amount of pendant vinyl groups on alternate carbon atoms of the polydiene backbone with (2) one gram mole of an aliphatic or aromatic acid anhydride capable of reacting with the polyfunctional groups of the polydiene to form a carboxylic acid terminated adduct; B. mixing the polydiene carboxylic acid terminated adduct with (3) a peroxide free radical initiator and (4) one equivalent of an aliphatic or aromatic chain extender capable of reacting with the adduct; C. reacting the adduct and the chain extender to form an elastomeric polymeric material having the peroxide initiator homogeneously dispersed therethrough substantially unreacted; and D. subsequently curing the elastomer to a hard thermoset resin.
Claim 15
Dependent Claim
20 words
A method according to claim 11 wherein the polydiene is selected from the group consisting of 1,2-polybutadiene and 3, 4-polyisoprene.
Claim 16
Dependent Claim
54 words
A method according to claim 11 wherein the acid anhydride 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, and phthalic anhydride.
Claim 17
Dependent Claim
56 words
A method according to claim 11 wherein said chain extender is selected from the group consisting of alkylene diepoxide, cycloalkylene diepoxide, alkoxyarylene diepoxide, arylene diepoxide, alkylcycloalkylene diepoxide, cycloalkene diepoxide, alkenecycloalkylene diepoxide, alkylene diimine, arylene diimine, alkarylene diimine, arylene diamine, arylalkylenimine, alkylenimine, alkarylene diamine, oxyarylene diamine, cycloalkylene diol, cycloalkylalkylene diol, aralkylene diol, alkylene diol, and arylene diol.
Claim 18
Dependent Claim
32 words
A method according to claim 11 wherein the acid anhydride is selected from the group consisting of 3,3'',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)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-12-09 | 1978-06-10 | 1978-12-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-12-09 | 1982-06-10 | 1982-12-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-12-09 | 1986-06-10 | 1986-12-10 | $7700.00 | Window Closed / Lapsed |