USRE28569E
Expired / Lapsed
US
⏱️ 0.0 years remaining
In situ process for transisomerization and conjugation of resins containing fatty acid esters
Assignee: —
•
Filing: 1973-06-25
•
Granted: 1975-10-14
•
Expires: 1993-06-25
Abstract
Abstract A method is provided for producing resins or esters from starting esterifiable components and polyunsaturated, nonconjugated fatty acids whereby the mass is heated in intimate admixture with sulfur dioxide gas to effect conjugation in situ and also rearrangement to provide increased isolated trans double bonds. The esterifiable components are suitably epoxy resins or alkyd-forming mixtures.
Inventors
No inventors recorded.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 02:28
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/14; C08G59/1433; C08G59/1438; C08G59/1455; C08G59/1461; C08G59/1472; C08G63/00; C08G63/02; C08G63/12; C08G63/46; C08G63/48; C09; C09D; C09D167/00; C09D167/08; C09F; C09F7/00; C09F7/08
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
203 words
A PROCESS FOR MAKING A COATING RESIN WHICH COMPRISES: A. ADMIXING A POLYUNSATURATED, UNCONJUGATED FATTY ACIDPROVIDING SUBSTANCE CHOSEN FROM THE GROUP CONSISTING OF LINOLEIC ACID, SAFFLOWER OIL, SUNFLOWER OIL, WALNUT OIL SOY OIL LINOLEIC ACID-ENRICHED TALL OIL FATTY ACIDS AND SEGREGATED COTTONSEED OIL FATTY ACIDS AND B. AN ESTERIFICATION COMPONENT WHICH IS AN EPOXY RESIN LIQUID AT THE TEMPERATURE OF REACTION OR AN ALKYD RESIN FORMING MIXTURE OF A POLYHYDRIC ALCOHOL AND A POLYBASIC CARBOXYLIC ACID-PROVIDING MATERIAL, C. HEATING SAID ADMIXTURE TO A TEMPERATURE OF FROM 425*F. TO 550*F. TO CAUSE SAID SUBSTANCE AND SAID RESIN OR ALKYDFORMING MIXTURE TO REACT, D. BUBBLING SULFUR DIOXIDE GAS THROUGH SAID ADMIXTURE (ALL) DURING AT LEAST A FINAL PORTION OF STEP (S) AND ALL DURING STEP E, (AND) E. REACTING SAID SUBSTANCE AND SAID RESIN OR ALKYD-FORMING MIXTURE TO FORM A CONJUGATED RESIN HAVING AN INCREASED PROPORTION OF TRANS TRANS CONJUGATION AS COMPARED WITH CONJUGATED PRODUCT NOT REACTED IN THE PRESENCE OF SULFUR DIOXIDE, AND ALSO HAVING MANY ISOLATED TRANS BONDS, AND F. THEN, WHEN A DESIRED ACID VALUE AND CONJUGATION HAVE BEEN ATTAINED, DISCONTINUING FLOW OF SULFUR DIOXIDE, PURGING SULFUR DIOXIDE FORM SAID CONJUGATED RESIN BY BLOWING WITH INERT GAS, AND RECOVERING SAID CONJUGATED RESIN.
Claim 2
Dependent Claim
203 words
A PROCESS FOR MAKING A COATING RESIN WHICH COMPRISES: A. ADMIXING A POLYUNSATURATED, UNCONJUGATED FATTY ACIDPROVIDING SUBSTANCE CHOSEN FROM THE GROUP CONSISTING OF LINOLEIC ACID, SAFFLOWER OIL, SUNFLOWER OIL, WALNUT OIL SOY OIL LINOLEIC ACID-ENRICHED TALL OIL FATTY ACIDS AND SEGREGATED COTTONSEED OIL FATTY ACIDS AND B. AN ESTERIFICATION COMPONENT WHICH IS AN EPOXY RESIN LIQUID AT THE TEMPERATURE OF REACTION OR AN ALKYD RESIN FORMING MIXTURE OF A POLYHYDRIC ALCOHOL AND A POLYBASIC CARBOXYLIC ACID-PROVIDING MATERIAL, C. HEATING SAID ADMIXTURE TO A TEMPERATURE OF FROM 425*F. TO 550*F. TO CAUSE SAID SUBSTANCE AND SAID RESIN OR ALKYDFORMING MIXTURE TO REACT, D. BUBBLING SULFUR DIOXIDE GAS THROUGH SAID ADMIXTURE (ALL) DURING AT LEAST A FINAL PORTION OF STEP (S) AND ALL DURING STEP E, (AND) E. REACTING SAID SUBSTANCE AND SAID RESIN OR ALKYD-FORMING MIXTURE TO FORM A CONJUGATED RESIN HAVING AN INCREASED PROPORTION OF TRANS TRANS CONJUGATION AS COMPARED WITH CONJUGATED PRODUCT NOT REACTED IN THE PRESENCE OF SULFUR DIOXIDE, AND ALSO HAVING MANY ISOLATED TRANS BONDS, AND F. THEN, WHEN A DESIRED ACID VALUE AND CONJUGATION HAVE BEEN ATTAINED, DISCONTINUING FLOW OF SULFUR DIOXIDE, PURGING SULFUR DIOXIDE FORM SAID CONJUGATED RESIN BY BLOWING WITH INERT GAS, AND RECOVERING SAID CONJUGATED RESIN.
Claim 3
Dependent Claim
13 words
The process of claim 1 wherein said fatty acid-providing substance is linoleic acid.
Claim 4
Dependent Claim
22 words
The process of claim 1 wherein said acid-providing substance is linoleic acid-enriched tall oil fatty acid containing about 81 percent linoleic acid.
Claim 5
Dependent Claim
14 words
The process of claim 1 wherein said fatty acid-providing substance is nonbreak safflower oil.
Claim 6
Dependent Claim
42 words
The process of claim 1 wherein said esterification component is epoxy resin having a weight per epoxy group of from 875 to 1, 025 and a Gardner-Holdt viscosity of from R to U at 40 percent nonvolatile in diethylene glycol monobutyl ether.
Claim 7
Dependent Claim
33 words
The process of claim 1 wherein said esterification component is a mixture of glycerol and a carboxylic acid providing material selected from the group consisting of phthalic acid, isophthalic acid and phthalic anhydride.
Claim 8
Dependent Claim
22 words
The process of claim 1 wherein said fatty acid-providing substance is nonbreak safflower and said esterification component is glycerol and isophthalic acid.
Claim 9
Dependent Claim
29 words
The process of claim 1 wherein said sulfur dioxide gas is added at a rate of from 0.1 to 2.0 liters per minute per 1000 grams of reaction admixture.
Claim 10
Dependent Claim
11 words
The process of claim 1 wherein said polyhydric alcohol is glycerol.
Claim 11
Dependent Claim
24 words
The process of claim 1 wherein said polybasic acid-providing material is selected from the group consisting of phthalic acid, isophthalic acid and phthalic anhydride.
Claim 12
Dependent Claim
150 words
A process for making a coating resin which comprises: a. preparing an admixture of nonconjugated safflower oil and isophthalic acid, b. heating said admixture to provide a liquid reaction mass and to form a partial glyceride of fatty acids and isophthalic acid, c. then reducing the temperature of said reaction mass to 430* F. and heating at said latter temperature with glycerol to effect esterification and to form a resin of the desired properties, and d. bubbling sulfur dioxide gas through said reaction mass during both said heatings at a rate of about 2 liters per minute of sulfur dioxide per 2,500 grams of said reaction mixture until said resin of desired properties and desired conjugation is obtained, as indicated by a desired degree of viscosity and a desired level of acid value, then discontinuing flow of sulfur dioxide and purging said reaction mass by blowing with inert gas .
Claim 13
Dependent Claim
150 words
A process for making a coating resin which comprises: a. preparing an admixture of nonconjugated safflower oil and isophthalic acid, b. heating said admixture to provide a liquid reaction mass and to form a partial glyceride of fatty acids and isophthalic acid, c. then reducing the temperature of said reaction mass to 430* F. and heating at said latter temperature with glycerol to effect esterification and to form a resin of the desired properties, and d. bubbling sulfur dioxide gas through said reaction mass during both said heatings at a rate of about 2 liters per minute of sulfur dioxide per 2,500 grams of said reaction mixture until said resin of desired properties and desired conjugation is obtained, as indicated by a desired degree of viscosity and a desired level of acid value, then discontinuing flow of sulfur dioxide and purging said reaction mass by blowing with inert gas .
Claim 14
Dependent Claim
139 words
A process for making a coating resin exhibiting higher than normal trans-trans conjugation which comprises: a. preparing an admixture of linoleic acid-enriched tall oil containing about 81% linoleic acid and an epoxy resin having a molecular weight per epoxy group of from 875 to 1,025 and a Gardner-Holdt viscosity of from R to U at 40 percent nonvolatile in Butyl carbitol, to form a reaction mixture, b. heating said reaction mixture at 500* F. to cause reaction, and c. bubbling sulfur dioxide gas therethrough during a final portion of said heating, at a rate of two liters per minute per 2,400 grams of said reaction mixture until the reaction product exhibits the desired acid number and viscosity then discontinuing flow of sulfur dioxide and purging said reaction mixture by blowing with inert gas , and d. recovering said product.
Claim 15
Dependent Claim
139 words
A process for making a coating resin exhibiting higher than normal trans-trans conjugation which comprises: a. preparing an admixture of linoleic acid-enriched tall oil containing about 81% linoleic acid and an epoxy resin having a molecular weight per epoxy group of from 875 to 1,025 and a Gardner-Holdt viscosity of from R to U at 40 percent nonvolatile in Butyl carbitol, to form a reaction mixture, b. heating said reaction mixture at 500* F. to cause reaction, and c. bubbling sulfur dioxide gas therethrough during a final portion of said heating, at a rate of two liters per minute per 2,400 grams of said reaction mixture until the reaction product exhibits the desired acid number and viscosity then discontinuing flow of sulfur dioxide and purging said reaction mixture by blowing with inert gas , and d. recovering said product.
Claim 16
Dependent Claim
40 words
The coating resin resulting from the product of claim 12, characterized by lower acid number and lower viscosity than resin made by treating the linoleic acid-enriched tall oil fatty acids with sulfur dioxide before reacting it with the epoxy resin.
Claim 17
Dependent Claim
10 words
The coating resin resulting from the process of claim 1.
Claim 18
Dependent Claim
10 words
The coating resin resulting from the process of claim 11.
Claim 19
Dependent Claim
189 words
A process for making a coating resin which comprises: a. admixing a polyunsaturated, unconjugated fatty acid-providing substance chosen from the group consisting of linoleic acid, safflower oil, walnut oil, sunflower oil, soy oil, linoleic-acid-enriched tall oil fatty acids and segregated cottonseed oil fatty acids, and b. an esterification component which is an alkyd resin-forming mixture of glycerol and a polybasic carboxylic acid-providing material, c. heating said admixture to a temperature of from 425* F. to 550* F. to cause said substance and said alkyd-forming mixture to react, d. bubbling sulfur dioxide gas through said admixture during at least a final portion of step c and during all of step e, and e. reacting said substance and said alkyd-forming mixture to form a conjugated resin having an increased proportion of trans trans conjugation as compared with a conjugated product not reacted in the presence of sulfur dioxide, and also having many isolated trans bonds, f. then, when the desired conjugation, viscosity, and acid value have been attained, discontinuing flow of sulfur dioxide, purging sulfur dioxide from said conjugated resin by blowing with inert gas, and g. recovering said conjugated resin.
Claim 20
Dependent Claim
189 words
A process for making a coating resin which comprises: a. admixing a polyunsaturated, unconjugated fatty acid-providing substance chosen from the group consisting of linoleic acid, safflower oil, walnut oil, sunflower oil, soy oil, linoleic-acid-enriched tall oil fatty acids and segregated cottonseed oil fatty acids, and b. an esterification component which is an alkyd resin-forming mixture of glycerol and a polybasic carboxylic acid-providing material, c. heating said admixture to a temperature of from 425* F. to 550* F. to cause said substance and said alkyd-forming mixture to react, d. bubbling sulfur dioxide gas through said admixture during at least a final portion of step c and during all of step e, and e. reacting said substance and said alkyd-forming mixture to form a conjugated resin having an increased proportion of trans trans conjugation as compared with a conjugated product not reacted in the presence of sulfur dioxide, and also having many isolated trans bonds, f. then, when the desired conjugation, viscosity, and acid value have been attained, discontinuing flow of sulfur dioxide, purging sulfur dioxide from said conjugated resin by blowing with inert gas, and g. recovering said conjugated resin.
Claim 21
Dependent Claim
26 words
A process as in claim 16 wherein said polybasic carboxylic acid-providing material is chosen from the group consisting of phthalic acid, isophthalic acid and phthalic anhydride.
Claim 22
Dependent Claim
10 words
The coating resin resulting from the process of claim 16.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-10-13 | 1979-04-14 | 1979-10-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-10-13 | 1983-04-14 | 1983-10-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-10-13 | 1987-04-14 | 1987-10-14 | $7700.00 | Window Closed / Lapsed |