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US3620989A Expired / Lapsed US ⏱️ 0.0 years remaining

Alkyds of unsaturated dibasic acids, polyols, and unsaturated fatty acid esters and method for making same: emulsion copolymerization of said alkyds with polymerizable monomers and the resulting polymers

Assignee: Pacific Vegetable Oil Corp
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Filing: 1969-09-15
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Granted: 1971-11-16
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Expires: 1989-09-15
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Abstract

Abstract A distinctive alkyd is made by reacting at a temperature below 350* F., an unsaturated dibasic acid or anhydride (e.g., maleic anhydride or fumaric acid) with an unsaturated fatty acid ester (e.g. safflower oil) that has been alcoholized with a polyol (e.g., ethylene glycol). This alkyd can then be emulsion copolymerized with various polymerizable monomers (e.g. vinyl acetate, styrene) to produce a high molecular weight polymer that is thermosetting and forms tough homogeneous films.

Inventors

  • 👤 Lowell O Cummings

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 15:14
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/02; C08G63/12; C08G63/52

Claims Analysis

Total Claims: 25
Claim 1
Independent Claim 32 words
The method of claim 1 in which in addition to the unsaturated dibasic acid material there is an amount of phthalic acid or phthalic anhydride smaller than that of said acid material.
Claim 2
Dependent Claim 39 words
The method of claim 1 in which the said partial ester is reacted with the said dibasic acid material until the resulting alkyd has a viscosity of at least about 12 stokes and an acid number below about 25.
Claim 3
Dependent Claim 22 words
The method of claim 1 in which the said partial ester is reacted with the said dibasic acid in substantially stoichiometric amounts.
Claim 4
Dependent Claim 27 words
The method of claim 1 in which the said vinylic monomer is from the group consisting of vinyl acetate, ethylhexyl acrylate, vinylidene chloride, styrene and butyl acrylate.
Claim 5
Dependent Claim 22 words
The method of claim 1 in which the said vinyl monomer is from the group consisting of vinyl, styryl and acryloyl monomers.
Claim 6
Dependent Claim 36 words
The method of claim 1 in which a peroxide is added to the said aqueous emulsion in quantity sufficient to initiate the said redox reaction and cause copolymerization of the said alkyd with said vinylic monomers.
Claim 7
Dependent Claim 21 words
The method of claim 7 in which said peroxide is of the group consisting of hydrogen peroxide, cumenehydroperoxide and diisopropylbenzene hydroperoxide.
Claim 8
Dependent Claim 32 words
The method of claim 7 in which sodium sulfoxylate formaldehyde is added to the said aqueous emulsion in small increments sufficient to maintain the copolymerization reaction at temperatures below about 130* F.
Claim 9
Dependent Claim 30 words
The method of claim 1 in which chelated iron ions are added to the Said aqueous reaction mixture in catalytic amounts below 0.01 percent sufficient to augment the copolymerization reaction.
Claim 10
Dependent Claim 20 words
The method of claim 1 in which the said aqueous emulsion has a pH below 4 during the redox reaction.
Claim 11
Independent Claim 135 words
The method of preparing an improved copolymer of a vinyl monomer and an alkyd, which comprises: a. partially alcoholizing an unsaturated fatty acid ester with a polyhydroxylalcohol, b. reacting the resulting partial ester with an unsaturated dibasic acidic material chosen from the group consisting of maleic acid, maleic anhydride, fumaric acid and itaconic acid at a reaction temperature not exceeding 350* F. sufficient to form an alkyd of said ester and said acidic material, so as to prevent substantial linking together of the double bond in the dibasic acid material and the double bonds of the partial ester, c. reacting the resulting alkyd at a temperature of from about 32* F. to about 131* F. with vinylic monomer by redox reaction while in an aqueous emulsion, and d. recovering the resulting copolymer from the emulsion.
Claim 12
Dependent Claim 37 words
The method of claim 12 in which said fatty acid ester is partially alcoholized by reflux boiling with the said alcohol in the presence of an alcoholysis catalyst until a temperature of about 450* F. is attained.
Claim 13
Dependent Claim 32 words
The method of claim 12 in which said fatty acid ester is partially alcoholized by heating with said alcohol to a temperature of about 450* F. in the presence of a catalyst.
Claim 14
Independent Claim 136 words
The method of preparing an improved copolymer of a vinyl monomer and an alkyd, which comprises: a. partially esterifying an unsaturated fatty acid with an excess of polyhydroxyalcohol, b. reacting the resulting partial ester with an unsaturated dibasic acidic material chosen from the group consisting of maleic acid, maleic anhydride, fumaric acid and itaconic acid at a reaction temperature not exceeding 350* F. sufficient to form an alkyd of said ester and said acidic material, so as to prevent substantial linking together of the double bond in the dibasic acid material and the double bonds of the partial ester, c. reacting the resulting alkyd at a temperature of from about 32* F. to about 131* F. with vinylic monomer by redox reaction while in an aqueous emulsion, and d. recovering the resulting copolymer from the emulsion.
Claim 15
Independent Claim 175 words
The method of preparing an improved copolymer of a vinyl monomer and an alkyd, which comprises: a. heating an unsaturated dibasic acid material chosen from the group consisting of maleic acid, maleic anhydride, fumaric acid and itaconic acid with the partial ester of (1) a polyol and (2) an unsaturated fatty acid or unsaturated fatty acid ester to a temperature not exceeding 350* F. sufficient to cause said dibasic material to react with said partial ester to form an alkyd and water, b. removing water formed during the reaction and continuing heating until reaction is complete, c. adding the resulting alkyd to an aqueous emulsion of a vinyl monomer while maintaining an emulsified condition, d. adding to the emulsion sufficient peroxide to initiate a redox reaction of copolymerization at a temperature of from about 32* F. to about 131* F. between the nonaqueous constituents of said emulsion, and e. adding to the emulsion in small increments sufficient sodium sulfoxylate formaldehyde to maintain the copolymerization at temperatures below about 130* F. until reaction is substantially complete.
Claim 16
Dependent Claim 40 words
The method of claim 16 in which the amount of the said alkyd added to the said aqueous emulsion is from 10 to 90 parts by weight of alkyd to 90 to 10 parts by weight of said vinyl monomer.
Claim 17
Independent Claim 117 words
The method of forming an alkyd from unsaturated fatty acids and dibasic acids, useful in the production of high-molecular weIght copolymers, which comprises: a. partially alcoholizing an unsaturated fatty acid ester with a polyhydroxylalcohol, b. mixing the resulting partial ester with an approximately stoichiometric amount of an unsaturated dibasic acid material chosen from the group consisting of maleic acid, maleic anhydride, fumaric acid and itaconic acid, and c. heating the resulting mixture to a temperature not substantially in excess of 350* F. sufficient to cause said partial ester to react with said acid material while not linking together, in substantial amount, the double bond of the dibasic acid material and the double bonds of the partial ester.
Claim 18
Dependent Claim 30 words
The method of claim 18 wherein, in addition to the dibasic acid material, an amount of phthalic acid or phthalic anhydride is used smaller than that of said acid material.
Claim 19
Independent Claim 115 words
The method of forming an alkyd from unsaturated fatty acids and dibasic acids, useful in the production of high-molecular weight copolymers, which comprises: a. partially esterifying an unsaturated fatty acid with an excess of polyhydroxyalcohol, b. mixing the resulting partial ester with an approximately stoichiometric amount of an unsaturated dibasic acid material chosen from the group consisting of maleic acid, maleic anhydride, fumaric acid and itaconic acid, and c. heating the resulting mixture to a temperature not substantially in excess of 350* F. sufficient to cause said partial ester to react with said acid material without substantially linking together the double bond of said dibasic acid material with the double bonds of the partial ester.
Claim 20
Dependent Claim 31 words
The method of claim 22 wherein, in addition to the unsaturated dibasic acid material, an amount of phthalic acid or phthalic anhydride is used smaller than that of said acid material.
Claim 21
Independent Claim 157 words
The method of preparing an alkyd useful in the production of high-molecular weight copolymers with vinylic monomers, which comprises: a. heating a mixture of about 2 to 5 parts of an unsaturated fatty oil and about 1 part of a polyalcohol in the absence of air at a temperature and for a time sufficient to raise the boiling point of the mixture to about 450* F., in the absence of substantial evaporation loss, b. adding about 1 to 3 parts of an unsaturated dibasic acidic material chosen from the group consisting of maleic acid, maleic anhydride, fumaric acid and itaconic acid and cooling the resulting mixture below about 350* F., and c. maintaining the temperature at about 350* F., while fractionating off water of esterification, until esterification is substantially complete, so that there is no substantial linking together of the double bond of the dibasic acid material and the double bonds of the product of step a.
Claim 22
Dependent Claim 25 words
The method of claim 22 in which the unsaturated fatty oil and polyalcohol are heated in the presence of effective amounts of an alcoholization catalyst.
Claim 23
Dependent Claim 40 words
The method of claim 22 in which the unsaturated fatty oil is selected from the group consisting of safflower, linseed, sunflower, soy, tung and tall oils, the fatty acids thereof, oleic, linoleic and linolenic acids, and the methyl esters thereof.
Claim 24
Dependent Claim 22 words
The method of claim 22 in which the polyalcohol is selected from the group consisting of glycerol, ethylene glycol, pentaerythritol and sorbitol.
Claim 25
Dependent Claim 108 words
In a process of preparing an alkyd useful in the production of high-molecular weight copolymers of vinylic monomers, the step comprising heating an approximately stoichiometric amount of an unsaturated dibasic acidic material chosen from the group consisting of maleic acid, maleic anhydride, fumaric acid and itaconic acid with the partial ester of a. a polyol and b. an unsaturated fatty acid or unsaturated fatty acid ester at a temperature not exceeding 350* F. sufficient to cause said dibasic material to react with said partial ester, while there is no substantial linking togEther of the double bond of the dibasic material with the double bonds of the partial ester.

References Cited (Backward Citations)

US2559466A Cited
US2850469A Cited
US3393165A Cited
US3350335A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1974-11-15 1975-05-17 1975-11-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1978-11-15 1979-05-17 1979-11-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1982-11-15 1983-05-17 1983-11-16 $7700.00 Window Closed / Lapsed

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