US2885297A - Production of drying oils - Google Patents

Production of drying oils Download PDF

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Publication number
US2885297A
US2885297A US600729A US60072956A US2885297A US 2885297 A US2885297 A US 2885297A US 600729 A US600729 A US 600729A US 60072956 A US60072956 A US 60072956A US 2885297 A US2885297 A US 2885297A
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US
United States
Prior art keywords
solution
aluminum
acid
fatty acids
preparing
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US600729A
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English (en)
Inventor
Reisinger Kurt Hans
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RICHARD NILSSON AB
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RICHARD NILSSON AB
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/06—Aluminium compounds
    • C07F5/069—Aluminium compounds without C-aluminium linkages
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
    • C09F5/00—Obtaining drying-oils

Definitions

  • a further object of the invention is the production of oils of the character described which can be used, for example, for lacquers, paints, varnishes, and other protective coatings, and which are adapted to furnish strong, more or less elastic films, resistant against any type of corrosion.
  • the oils can, furthermore, be used for the impregnation of textile fabrics, paper, and other fibrous material.
  • the method according to the invention substantially consists in preparing a solution, hereinbelow called first solution, by dissolving, in an inert solvent, one or more saturated or unsaturated higher aliphatic acids, for example, saturated fatty acids, or saturated cyclic acids, or mixtures of the same; preparing a second solution by dissolving one or more aluminum.
  • alcoholates such as aluminum butylate, amylate, or hexylate in an inert solvent, and thereafter converting the aluminum alcoholates into enolic aluminum compounds, and subjecting the first solution to a condensation reaction with the second solution in the absence of water and substances which generate water during the condensation.
  • the quantity of the second solution is so chosen as to contain a substoichiometric amount of aluminum enolate with respect to the acid present in the first solution.
  • the higher aliphatic acids contain at least 8 carbon atoms.
  • fatty acids having between 10 and 20 carbon atoms. Examples of such acids are: Palrnitic acid, coconut acids, stearic acid, whale oil fatty acids and the like.
  • the acid solution may contain refined tall oil or carboxylic acids contained in such oil. As already mentioned, a mixture of several acids may be used for the first solution.
  • the solvents for the acids and for the aluminum compound may consist of aliphatic or aromatic hydrocarbons, such as gasoline, xylene, benzene, and so on.
  • metal soaps particularly aluminum soaps by reaction of the corresponding aluminum alcoholates with fatty acids
  • the products obtained by the method according to the present invention are not aluminum soaps, but film-forming drying oils.
  • the production of aluminum soaps is avoided, because of the undesirable propertiesof these soaps. If aluminum soaps were. obtained unintentionally, they would be a gelatinous mass, even when diluted to a high extent, so that they would be useless for production of film-forming drying oils.
  • the reaction between the aluminum compounds and the fatty acids is directed to the formation of drying, film-forming oils by maintaining a predetermined ratio between the aluminum alco- 2,885,297 Patented May 5, 1959 holate and the tautomeric compound present in the reaction mixture, this ratio being at least one molecule aluminum alcoholate to one molecule of the tautomeric compound.
  • the conversion of the aluminum alcoholate into enolic form is carried out by heating the solution of the alco holate with the stoichiometric amount of a tautomeric' compound in enolic form for a period of from 1 to 3 hours in a temperature range of 100-135 C., according to the boiling points of the tautomeric compound and the solvent.
  • the following compounds are used in their enolic form: Diketones, diketo-carboxylic acid esters, dicarboxylic acid esters of the malonic-ester type, keto-aldelhydes, and beta keto esters.
  • Enolization by means of the ketonic additive is most effectively done when the parent carbonyl group, i.e. the enol-forming group and not the carbonyl group of carboxyl or aldehyde compound, is situated in a beta position to the nearest functional group.
  • the beta-keto compounds are the most effective.
  • unsaturated compounds give superior results over saturated.
  • the amount of aluminum (in solution) to be used with the fatty acids depends primarily on the amounts of fatty acids used and their acid number, furthermore on the equilibrium of the enolic and the alcoholic form of the aluminum compound used, and the desired properties of the film-forming oils.
  • the drying oils contain between 0.5 to 2.5% by weight of aluminum, and in any case the quantity of the aluminum compound should be substantially smaller than the equivalent amount of the acid in solution.
  • the concentration of the aluminum in the solvent is without importance.
  • any desired aliphatic or aromatic hydrocarbon may be used without affecting the quality of the resulting oils.
  • the heating period is independent of the concentration of the acids used, and so is the temperature. The latter only depends on the solvents used, and ranges in general presence of the last mentioned compounds prevents the formation of soaps.
  • the existence of co-valencies explains the formation of molecule chains as a presupposition for the drying mechanism.
  • Example 1 As a first solution I prepare a solution of 200 g. stearic acid in 250 g. warm white spirit. Then I start preparing the second solution by heating 246 g. of Al-butylate with,188 g. of malonic acid diethylester for 2'-3 hours, until the practical test shows that the enolization has been completed.
  • Example 2.-As a first solution I prepare a solution of 400 g. hydrogenated whaleoil fatty acids in 300 g. white spirit. Then I start preparing the second solution by heating 246 g. of Al-butylate with 104 g. acetoacetic ester for 23 hours until the practical test shows that the enolization has been completed.
  • Viscosity of the final product 160-170 DIN-seconds.
  • Example 3.-As a first solution I prepare a solution of 300 g. coconut fatty acids in 200 g. xylene. Then I prepare the second solution by heating 246 g. of Albutylate with 114 g. acetonylacetone for 2-3 hours until the practical test shows that the enolization has been performed.
  • Viscosity of the final product 40-50 DIN-seconds.
  • Example 4.-As a first solution I prepare a solution of 200 g. of mixed fatty acids (acid number 205, iodine number 15, melting point 45 C.) in 300 g. white spirit. Then I make the second solution by heating 246 g. of Albutylate with 91 g. acetoacetic ester for 2-3 hours, until the practical test shows that the enolization has been performed.
  • Viscosity of the final product 285 DIN-seconds.
  • Example 5 As a first solution I prepare a solution of 400 g. commercial tall oil (acid number 180, containing 90% free fatty acids) in 200 g. Tetraline (tetrahydronaphthalene). Then I start preparing the second solution for 2-3 hours, until the practical test shows that the enolization has been performed.
  • Viscosity of the final product 230-250 DIN-seconds.
  • Example 6A a first solution I prepare a solution of 400 g. distilled tall oil (acid number 200) in 175 g. white spirit. Then I prepare the second solution by heating 246 g. of Al-butylate with 130 g. acetoacetic ester for 2-3 hours, until the practical test shows that the enolization has been carried out.
  • Viscosity of the final product 120 DIN-seconds.
  • Example 7 As a first solution I prepare a solution of 300 g. fatty acids from linseed oil rafiination in 584 g. white spirit. Then I make the second solution by heating 246 g. of Al-butylate with 104 g. acetoacetit; ester for 2-3 hours, until the practical test shows that the enolization has been carried out.
  • Viscosity of the final product -100 DIN-seconds.
  • Example 8.-As a first solution I prepare a solution of 250 g. phenyl acetic acid in 426 g. white spirit. Then I prepare the second solution by heating 246 g. of A1- butylate with g. acetoacetic ester for 2-3 hours until the practical test shows that the enolization has been carried out.
  • Viscosity. of the final product 130-135 DIN-seconds.
  • a method of producing film-forming drying oils comprising the steps of preparing a first solution by dissolving, in an inert hydrocarbon solvent, at least one organic carboxylic acid having from 8-20 carbon atoms and being selected from the group consisting of saturated fatty acids, unsaturated fatty acids, and carbocyclic fatty acids; preparing a second inert hydrocarbon solution of an enolic aluminum compound obtained by reacting an aluminum alcoholate whose alcoholic component is selected from the group consisting of a butylate, an amylate, and a hexylate with an enolic compound selected from the group consisting of diketones, diketocarboxylic acid esters, malonic esters, ketoaldehydes, beta keto esters and acetone, mixing the first solution with a quantity of the second solution containing a substoichiometric amount of aluminum with respect to the acid in the first solution said substoichiometric amount being approximately two molecules of carboxylic acid from said first solution to one atom of
  • a method of producing film-forming drying oils comprising the steps of preparing a first solution by dissolving stearic acid in white spirit, preparing a second inert hydrocarbon solvent solution of an enolic aluminum compound obtained by reacting aluminum butylate with malonic acid diethylester, mixing the first solution with a quantity of the second solution containing a substoichiometric amount of aluminum with respect to said acid in the first solution, and refluxing the mixture for half an hour to bring about a condensation between the acid and the aluminum enolate.
  • a method of producing film-forming drying oils comprising the steps of preparing a first solution by dissolving hydrogenated whale oil fatty acids in white spirit, preparing a second inert hydrocarbon solvent solution of an enolic aluminum compound obtained by reacting aluminum butylate with aceto acetic ester for 23 hours, mixing the first solution with a quantity of the second solution containing a substoichiometric amount of aluminum withrespect to said acid in the first solution, and
  • a method of producing film-forming drying oils comprising the steps of preparing a first solution by dissolving coconut fatty acids in xylene, preparing a second inert hydrocarbon solvent solution of an enolic aluminum compound obtained by reacting aluminum butylate with acetyl acetonate for 2-3 hours, mixing the first solution with a quantity of the second solution containing a substoichiometric amount of aluminum with respect to said acid in the first solution, and refluxing the mixture for half an hour to bring about a condensation between the acid and the aluminum enolate.
  • a method of producing filrn-forming drying oils comprising the steps of preparing a first solution by dissolving tall oil in tetraline, preparing a second inert hydrocarbon solvent solution of an enolic aluminum compound obtained by reacting aluminum butylate with malonic acid diethyl ester for 23 hours, mixing the first solution with a quantity of the second solution con-"taining a substoicbiometric amount of aluminum with respect to said acid in the first solution, and refluxing the mixture for half an hour to bring about a condensation between the acid and the aluminum enolate.
  • a method of producing film-forming drying oils comprising the steps of preparing a first solution by d.issolving phenyl acetic acid in white spirit, preparing a sec ond inert hydrocarbon solvent solution of an enolic aluminum compound obtained by reacting aluminum butylate with aceto acetic ester for 2-3 hours, mixing the first solution with a quantity of the second solution containing a substoichiometric amount of aluminum with respect to said acid in the first solution, and refluxing the mixture for half an hour to bring about a condensation between the acid and the aluminum enolate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
US600729A 1951-07-11 1956-07-30 Production of drying oils Expired - Lifetime US2885297A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
SE1062632X 1951-07-11
SE761536X 1951-07-11
SE2885297X 1951-07-11
SE315887X 1951-07-11

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US2885297A true US2885297A (en) 1959-05-05

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BE (1) BE512751A (fr)
NL (1) NL88606C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050148714A1 (en) * 2004-01-06 2005-07-07 Lance Neimann Novel seed oil based coatings and their applications

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2160532A (en) * 1936-09-02 1939-05-30 Du Pont Esters
US2242230A (en) * 1941-05-20 Process of producing conjugation in
US2424458A (en) * 1942-12-12 1947-07-22 Heijmer Gustaf Bristol Emulsions for painting and varnishing purposes
US2513825A (en) * 1946-04-10 1950-07-04 Du Pont Preparation of ketenes
US2634279A (en) * 1949-07-16 1953-04-07 Eastman Kodak Co Preparation of monoglycerides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2242230A (en) * 1941-05-20 Process of producing conjugation in
US2160532A (en) * 1936-09-02 1939-05-30 Du Pont Esters
US2424458A (en) * 1942-12-12 1947-07-22 Heijmer Gustaf Bristol Emulsions for painting and varnishing purposes
US2513825A (en) * 1946-04-10 1950-07-04 Du Pont Preparation of ketenes
US2634279A (en) * 1949-07-16 1953-04-07 Eastman Kodak Co Preparation of monoglycerides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050148714A1 (en) * 2004-01-06 2005-07-07 Lance Neimann Novel seed oil based coatings and their applications
US7119135B2 (en) 2004-01-06 2006-10-10 Green Products Llc Seed oil based coatings and their applications

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BE512751A (fr) 1954-02-19
NL88606C (fr)

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