US2221975A - Zirconium salts of water-insoluble fatty acids and methods of making same - Google Patents

Zirconium salts of water-insoluble fatty acids and methods of making same Download PDF

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US2221975A
US2221975A US98068A US9806836A US2221975A US 2221975 A US2221975 A US 2221975A US 98068 A US98068 A US 98068A US 9806836 A US9806836 A US 9806836A US 2221975 A US2221975 A US 2221975A
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Charles J Kinzie
Wainer Eugene
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Tam Ceramics LLC
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Titanium Alloy Manufacturing Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part

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  • Fatty acids as employed in our present invention are stearicjpalmitic, oleic,'the'acids of tung oil as well as of linseed oil.
  • fattyacids as are derived from animal and vegetable fats and oils are utilized.
  • the zirconium salts as finally prepared according to our invention are designed for use in producing opalescent or fiat finish in fibers, films, varnishes, lacquers, paints, resins, inks, and the like without developing the cheesy or spongy appearance obtained by use of other metallic soaps, but still producing the same or a better measure of flattening. Incorporation of such derivatives further increases the water-proofness o of the final product.
  • Derivatives such as the oleate, or the mixture hereinafter described as linoleate, which are essentially very viscous greases, have, in addition to the flattening properties noted above desired usefulness as an addition to heavy lubricating greases in which considerable friction work is to be done.
  • the zirconium soaps are water-proof materials whose physical characteristics are depend out on the type of fatty acid used as the starting material, and are derivatives of bivalent zir; conyl radical (ZrO++) groupings as set forth in the hereinafter enumerated examples.
  • Example 1 To a concentrated water solution ofzirconium oxychloride, or zirconium sulphate, or zirconium nitrate containing the equivalent of 108 grams of zirconium oxide are added v1 liter of water and 520 grams of stearicacid; the solution is then heated until the acid-melts complete-- ly. 140 cc. of a 50% caustic soda solution are added slowly with stirring together'with sumcient cold' water to allow the stiffening mass to be easily stirred. Such alkaline mix is stirred violently for several minutes at 50-75 C. and is then cooled to room temperature with continued stirring. The longer and more violent the stirring this slightly alkaline mix receives at this stage of our procedure, the product.
  • the stirred mix is then neutralized with acid, drop by drop, until the supernatant liquor is, and permanently Violent stirring at this stage also aids in a finer end product. If the acid. neutralization is carried out above the softening" point of final compound at 65-'70 0., complete agglomeration of the metallic soap to a very viscous grease takes place, thereby making subsequent handling very diificult in case Accelepowder is desired.
  • Example 4 To a concentrated water solution of zirconium oxychloride, or zirconium sulphate,
  • zirconium nitrate containing the equivalent of 108 grams of zirconium oxide is added 1 liter of tested to by the facts that the material (1) is 'miscible with oils, (2) does not give up water on water together with 470 grams of palmitic acid; the solution is heated until the acid melts completely. 140 cc. of a 50% caustic soda. solution are added slowly with stirring together withsufficient cold water to allow the stiffening mass j to be easily stirred. The alkaline mix is, Stirred violently at 50-75" C. for several minutes. and is then cooled to 15 C. with continued stirring. The stirred mix is neutralized with acid, drop by drop, until the supernatant liquor is, and permanently remains, just acid to litmus'paper.
  • Example 5 Saponify 470 grams of palmitlc acid with 140 cc. of a 50% caustic soda solution; then dissolve the resultant mix in warm water and add with stirring at .50-75 C. a concentrated solution of zirconium oxychloride,"or zirconium sulphate, or zirconium nitrate, which contains the equivalent of 108 grams of zirconium oxide. Then cool to 15 C. with stirring, and proceed as set forth in Example 4.
  • Example 6 To a concentrated water solution of zirconium oxychloride, or zirconium sulphate, or zirconium nitrate containing the equivalent of 108 grams of zirconium oxide,- 1 liter of water is added together with 2 liters of a warm solution of 513 grams of sodium palmitate. This mix is then heated to 50-75 C. with stirring, and then we add 50 cc. of a 50% caustic soda solution, and proceed as set forth in Example 4, after cooling to 15 C.
  • Example 7 To a concentrated water solution of zirconium oxychloride, or zirconium sulphate, or zirconium nitrate, containing the equivalent of 61.5 grams of zirconium oxide, are added 500 cc. of water and 282.3 grams of oleic acid. This mix is heated to 50 C. and then 70 cc. of a 50% caustic soda solution are added slowly with stirring. This alkaline mix is cooled to 5 C. while stirring. This mix is then neutralized with acid, drop by drop, until the supernatant liquor is, and permanently remains, just acid'to litmus, while being stirred vigorously. We filter and wash the slightly tacky solid on the centrifuge until all soluble salts are removed, but notallowing the temperature to rise above 5 C. On warming to room temperature, the white. tac y grams of zirconium oxide.
  • Example 8. -Saponify- 282.3 grams of oleic' acid with 70 ,cc. of a 50% caustic soda solution; the resultant mix is then-dissolved in a liter of warm water, while adding with stirring a concentrated solution of zirconium oxychloride, o'r zirconium sulphate, or zirconium nitrate, equivalent to 61.5 We then cool with or zirconium nitrate equivalent to 61.5 grams of oxide, are added 304 grams of sodium oleate previously dissolved in 2 liters of warm water. This mix is then heated to 50 C. to which are added- 16 cc. of a ,50% caustic soda solution and then cooled to-5 C., we then proceed as set forth in Example 7.
  • Example 10.-221.2 grams of tung oil are completely saponifled with 70 cc. of a 50% caustic soda solution; the resultant mix is thendissolved in two liters of warm water.
  • Sufllcient cold water is added to allow the stiffening mixture to be easily stirred.
  • the mixture is then cooled with stirring to room temperature and is neutralized with acid; it is then filtered and washed with water at 15 C. on the centrifuge until all soluble salts and glycerine are removed.
  • the centrifuge discharge is a pale tan, soft, fluffy powder which air dries easily to a faintly tacky solid at room temperatures.
  • the yield equals 340 grams.
  • Tung oil is a mixture of olein and oleomargarin.
  • Zirconyl tungate is a mixture of zirconyl oleate ZrO(CaH1'1CHtCH(CH2) 7000) aXHcO and Zirconyl eleomargarate ZrO(C1aH31O2) having an average empirical formula Example 11 .205.9 grams of raw linseed oil are completely sa-ponified with 70 cc.
  • Linseed oil is a mixture or isolinolein, linolin, linolein,olein,stearin,palmitin.
  • the zirconium soaps prepared therefrom are mixtures of the following formulae: I
  • Zr0(CHa(CHz)1eCO0)z zirconyl stearate
  • linseed oil also contains acids of following empirical composition after saponiflcation C1aH25.COOH C1cH27.COOH
  • zirconium soaps of formula ZrO (C1sH25COO) 2 and ZrO(C1sH27COO) 2 Q
  • the average empirical formula for the total mixture used is ZIO(C1'1H31O2)2.XH2O).
  • the zirconium stearate, zirconium palmitate, zirconium oleate, zirconium tungate or zirconium linoleate above described or any suitable mixture of these metallic soaps are mixed by milling, crutching, or similar suitable procedure in accordance. with the end in view, in a dosage of 1.5 to 10 oz. per gallon of the paint, varnish, lacquer, ink, raw fiber solution, etc.
  • a flat, deglossed, more waterproof finish is obtained, free from the cheesy or spongy appearance given by other commercially used metallic soaps.
  • the method of preparing a zirconium salt of water-insoluble fatty acids which comprises mixing an aqueous solution of a water-soluble inorganic salt of zirconium and the fatty acid in the ratio of 1 mol of ZIO: to 2 mols of said acid at temperatures sufiicient to melt the fatty acid, then adding an alkali solution with stirring, cooling the resulting alkaline mix and neutralizing same to acid with precipitation of solid material, and finally washing and dewateringthe resulting solid material.
  • the method of preparing anhydrous zirconyl palmitate which comprises mixing an aquezirconium in the ratio of 1 mol ous solution of a water-soluble inorganicsalt of zirconium and palmitic'acid in the ratimof 1 mol of ZrO: to '2 mols of said acid at temperatures suflicient to melt said acid, then ad gan'alkali solution with stirring, cooling the resulting alkaline mix and; neutralizing same to acid with pre ipita .tion of solid material, and finally washlng'an'd dewat ering said solid material to form' the anhydrous zirconyl palmitate.
  • Themethod of preparing zirconyl'oleate which comprises mixing an aqueous solution of a water-soluble inorganic salt of zirconium and oleic acid in the ratio of 1 mol of ZrOa to 2 mols of said acid at temperatures sufficient to melt said'acid, then adding an alkali solution with stirring, cooling the resulting alkaline mix and neutralizing same to acid with precipitation of solid material, and finally washing and dewatering said solid material to form the anhydrous zirconyl oleate.
  • the step which consists in mixing an aqueous saponified solution of said acid with a water-soluble inorganic salt of zirconium in the ratio of 1 mol of ZrOz to 2 mols of said acid at temperatures between 50 C. and 75 C.
  • the step which consists in mixing an aqueous saponified solution ofstearic acid with a water-soluble inorganic salt of zirconium in the ratio of 1 mol of ZIO: to 2 mols of said acid at temperatures between 50 C. and 75 C.
  • the step which consists in mixing an aqueous saponi-' fled solution of palmitic acid with awater-soluble inorganic salt of zirconium in the ratio of 1 mol of ZrOz to 2 mols of said acid at temperatures" between 50 C. and 75 C.
  • the step which consists in mixing an aqueous saponified solution of'oleic acid with a water-soluble inorganic salt of zirconium in the ratio of 1 mol of ZrOz to 2 mols of said between 50 C. and 75 C.
  • a waterproof fatty acid soap of zirconium of the formula Z1O(RCOO)2 substantially free of RCOOH and water soluble compounds, wherein R represents a higher alkyl radical.

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Description

Patented Nov. 19, 1940 g r UNITED s AT s ZIRCONIUM sAL'rs 0F WATER-INSOLUBLE FATTY ACIDS SAME AND METHODS OF MAKING Charles J. Kinzic and Eugene Wainer, Niagara Falls, N. Y., assignors to The Titanium Alloy Manufacturing Company, New York, N. Y., a
corporation of Maine No Drawing.
Application August 26, 1936, Serial No. 98,068
Claims. (01. 260 -414) 5 soluble inorganic salt of zirconium and the (lasired fatty acid, or sodium salt of the fatty acid,-
cedures; for example, by treatment of thefat oroil with superheated steam followed by='distillation to recover free fatty acid, -or the saponification of the fat or oil with caustic soda, and the subsequent separation of the sodium derivative by the addition of salt in common with general soap making procedures.
Fatty acids as employed in our present invention are stearicjpalmitic, oleic,'the'acids of tung oil as well as of linseed oil. In other words, such fattyacids as are derived from animal and vegetable fats and oils are utilized.
The zirconium salts as finally prepared according to our invention are designed for use in producing opalescent or fiat finish in fibers, films, varnishes, lacquers, paints, resins, inks, and the like without developing the cheesy or spongy appearance obtained by use of other metallic soaps, but still producing the same or a better measure of flattening. Incorporation of such derivatives further increases the water-proofness o of the final product.
Derivatives such as the oleate, or the mixture hereinafter described as linoleate, which are essentially very viscous greases, have, in addition to the flattening properties noted above desired usefulness as an addition to heavy lubricating greases in which considerable friction work is to be done.
The zirconium soaps are water-proof materials whose physical characteristics are depend out on the type of fatty acid used as the starting material, and are derivatives of bivalent zir; conyl radical (ZrO++) groupings as set forth in the hereinafter enumerated examples.
Our invention, broadly stated, consists not only in the discovery of our new zirconium :salts of Water-insoluble fatty acids, but also in the discovery that by the novel methods as fully described in the following examples zirconium soaps may be prepared for use as flattening agents as well as constituents for lubricating greases, all as hereinbefore described. 1
Methods of Procedure remains, just acid to litmus paper.
Example 1.To a concentrated water solution ofzirconium oxychloride, or zirconium sulphate, or zirconium nitrate containing the equivalent of 108 grams of zirconium oxide are added v1 liter of water and 520 grams of stearicacid; the solution is then heated until the acid-melts complete-- ly. 140 cc. of a 50% caustic soda solution are added slowly with stirring together'with sumcient cold' water to allow the stiffening mass to be easily stirred. Such alkaline mix is stirred violently for several minutes at 50-75 C. and is then cooled to room temperature with continued stirring. The longer and more violent the stirring this slightly alkaline mix receives at this stage of our procedure, the product.
After cooling to room temperature, the stirred mix is then neutralized with acid, drop by drop, until the supernatant liquor is, and permanently Violent stirring at this stage also aids in a finer end product. If the acid. neutralization is carried out above the softening" point of final compound at 65-'70 0., complete agglomeration of the metallic soap to a very viscous grease takes place, thereby making subsequent handling very diificult in case afinepowder is desired.
After the acid neutralization, the supernatant liquor is decanted off, and the solid is washed and dewatered completely in a high speed centrifuge until soluble ions are practically all removed. The centrifuge discharge is a brilliant-white, par-- tially dry powdered material which air-dries rapidly when placed in flat trays in'a current of cool air. Precipitation of anhydrous zirconyl stearate is quantitative, producing 617 rams of product having the formula 0 ZrO (CH3 (CH2) isCOO) 2 therebyshowlng the presence of the bivalent zir-' conyl radical ZrO++.
- Example 2.Saponify 520 grams of stearic acid Example 3.-To aconcentrated water solution.
of zirconium oxychlorideor zirconium sulphate, or zirconium nitrate containing the equivalent of;108 grams of zirconium oxide, 1 liter of water is added together with 2 liters of a warm solumore finely divided the final PATENT? orrlce tion of 560 grams of sodium stearate. Heat to 50-75 C. with stirring, and add 50 cc. of a 50% caustic soda solution, and then proceed as set forth in Example 1, after cooling to room temperature.
Example 4.-To a concentrated water solution of zirconium oxychloride, or zirconium sulphate,
or zirconium nitrate containing the equivalent of 108 grams of zirconium oxide is added 1 liter of tested to by the facts that the material (1) is 'miscible with oils, (2) does not give up water on water together with 470 grams of palmitic acid; the solution is heated until the acid melts completely. 140 cc. of a 50% caustic soda. solution are added slowly with stirring together withsufficient cold water to allow the stiffening mass j to be easily stirred. The alkaline mix is, Stirred violently at 50-75" C. for several minutes. and is then cooled to 15 C. with continued stirring. The stirred mix is neutralized with acid, drop by drop, until the supernatant liquor is, and permanently remains, just acid to litmus'paper.
Violent stirring at this stage aids in a more com-' plete comminution of the final product. Ifjacid neutralization is carried out above the softening point of final compound, for example 35-40904;
complete agglomeration of the -metallicv soap to;:' a very viscous grease takes place, thereby'making subsequent handling i cult in case affinely divided product is desired. a
After the acidneutralizationi the supernatant liquor is decanted ofl, and the solid is'washed and dewatered completely on a; high speed centrifuge until soluble ions are practicallyremoved. "The centrifuge discharge is a pale tan. slightly tacky, partially dry material, which air dries rapidly in a current of cool air. "Precipitationofan hydrouszirconyl palmitate is quantitative. 567 grams of final product obtained having the formula Z1'O(CH3(CH2)14COO)2, thereby-showing the presence of the bivalent zirconyl radical Zr0++.
Example 5.Saponify 470 grams of palmitlc acid with 140 cc. of a 50% caustic soda solution; then dissolve the resultant mix in warm water and add with stirring at .50-75 C. a concentrated solution of zirconium oxychloride,"or zirconium sulphate, or zirconium nitrate, which contains the equivalent of 108 grams of zirconium oxide. Then cool to 15 C. with stirring, and proceed as set forth in Example 4.
Example 6.To a concentrated water solution of zirconium oxychloride, or zirconium sulphate, or zirconium nitrate containing the equivalent of 108 grams of zirconium oxide,- 1 liter of water is added together with 2 liters of a warm solution of 513 grams of sodium palmitate. This mix is then heated to 50-75 C. with stirring, and then we add 50 cc. of a 50% caustic soda solution, and proceed as set forth in Example 4, after cooling to 15 C.
Example 7.-To a concentrated water solution of zirconium oxychloride, or zirconium sulphate, or zirconium nitrate, containing the equivalent of 61.5 grams of zirconium oxide, are added 500 cc. of water and 282.3 grams of oleic acid. This mix is heated to 50 C. and then 70 cc. of a 50% caustic soda solution are added slowly with stirring. This alkaline mix is cooled to 5 C. while stirring. This mix is then neutralized with acid, drop by drop, until the supernatant liquor is, and permanently remains, just acid'to litmus, while being stirred vigorously. We filter and wash the slightly tacky solid on the centrifuge until all soluble salts are removed, but notallowing the temperature to rise above 5 C. On warming to room temperature, the white. tac y grams of zirconium oxide.
to :5" C. and proceed as in Example 7. *Ezamplei-To a concentrated water solution 0f zirconium oxychloride, or zirconium sulphate,
solid takes on the consistency of a very viscous grease weighing 330 grams having the formula ties of a very viscous grease. The weight of such a product obtained in this example is 830 grams.
The permanency of this water emulsion is atviole'nt crutching, (8) does notglose weight appreciably on standing in the openiair, (4) does not give up water on long standing.
Example 8.-Saponify- 282.3 grams of oleic' acid with 70 ,cc. of a 50% caustic soda solution; the resultant mix is then-dissolved in a liter of warm water, while adding with stirring a concentrated solution of zirconium oxychloride, o'r zirconium sulphate, or zirconium nitrate, equivalent to 61.5 We then cool with or zirconium nitrate equivalent to 61.5 grams of oxide, are added 304 grams of sodium oleate previously dissolved in 2 liters of warm water. This mix is then heated to 50 C. to which are added- 16 cc. of a ,50% caustic soda solution and then cooled to-5 C., we then proceed as set forth in Example 7.
Example 10.-221.2 grams of tung oil are completely saponifled with 70 cc. of a 50% caustic soda solution; the resultant mix is thendissolved in two liters of warm water. To the stirred solution at 50-75 C. is added a concentrated solution of zirconium oxychloride, or zirconium sulphate, or zirconium nitrate containing the equivalent of. 12.7 grams of zirconium oxide. Sufllcient cold water is added to allow the stiffening mixture to be easily stirred. The mixture is then cooled with stirring to room temperature and is neutralized with acid; it is then filtered and washed with water at 15 C. on the centrifuge until all soluble salts and glycerine are removed. The centrifuge discharge is a pale tan, soft, fluffy powder which air dries easily to a faintly tacky solid at room temperatures. The yield equals 340 grams. Tung oil is a mixture of olein and oleomargarin. Zirconyl tungate is a mixture of zirconyl oleate ZrO(CaH1'1CHtCH(CH2) 7000) aXHcO and Zirconyl eleomargarate ZrO(C1aH31O2) having an average empirical formula Example 11 .205.9 grams of raw linseed oil are completely sa-ponified with 70 cc. of a 50% caustic soda solution; the resultant mix is then dissolved in 2 litersof warm water. To the stirred solution at 50 C. is added a concentrated solution of zirconium oxychloride, or zirconium sulphate, or zirconium nitrate containing the equivalent of 42.7 grams of zirconium oxide. Sufficient .cold water is added to allow the stiflening mixture to be easily stirred. The mix is then cooled with stirring to 5 C. and neutralized with acid until the supernatant liquor is, and remains, just acid; it is then filtered and washed on. the centrifuge with water at 5 C. until all soluble salts and glycerine are removed. The centrifuge discharge is a tacky pale yellow solid which becomes a very g ams.
Linseed oil is a mixture or isolinolein, linolin, linolein,olein,stearin,palmitin.
The zirconium soaps prepared therefrom are mixtures of the following formulae: I
Zr0(CHa(CHz)1eCO0)z=zirconyl stearate Each of the above formulae shows the presence of the zirconyl radical ZrO++.
According to some authorities linseed oil also contains acids of following empirical composition after saponiflcation C1aH25.COOH C1cH27.COOH
which will form zirconium soaps of formula ZrO (C1sH25COO) 2 and ZrO(C1sH27COO) 2 Q The average empirical formula for the total mixture used is ZIO(C1'1H31O2)2.XH2O).
If the acid neutralization is carried out at room temperatures, a permanent and stiff emulsion of the consistency of heavy rubbery grease. is formed, having a paleryellow color, weighing 835 grams. That this emulsion is permanent is shown from what we'have set forth in Example '7.
Usage As flattening agents, the zirconium stearate, zirconium palmitate, zirconium oleate, zirconium tungate or zirconium linoleate above described or any suitable mixture of these metallic soaps are mixed by milling, crutching, or similar suitable procedure in accordance. with the end in view, in a dosage of 1.5 to 10 oz. per gallon of the paint, varnish, lacquer, ink, raw fiber solution, etc. A flat, deglossed, more waterproof finish is obtained, free from the cheesy or spongy appearance given by other commercially used metallic soaps.
As a constituent of lubricating grease, from ten to seventy percent of the anhydrous soaps may be incorporated in the grease toincrease its lubricating life under heavy load. I
We claim as our invention: I
1. The method of preparing a zirconium salt of water-insoluble fatty acids, which comprises mixing an aqueous solution of a water-soluble inorganic salt of zirconium and the fatty acid in the ratio of 1 mol of ZIO: to 2 mols of said acid at temperatures sufiicient to melt the fatty acid, then adding an alkali solution with stirring, cooling the resulting alkaline mix and neutralizing same to acid with precipitation of solid material, and finally washing and dewateringthe resulting solid material.
2. The method of preparing anhydrous zirconyl stearate, which comprises mixing an aque-;
ous solution of a water-soluble inorganic salt of zirconium and stearic acid in the ratio of 1 mol of ZIOzlZO 2 mols of said acid at temperatures sufllcient to melt said acid, then adding an alkali solution with stirring, cooling the resulting. a1- kaline mix and neutralizing same to acid with precipitation of solid material, and finally washing and dewatering said solid material to form the anhydrous zirconyl stearate.
3. The method of preparing anhydrous zirconyl palmitate which comprises mixing an aquezirconium in the ratio of 1 mol ous solution of a water-soluble inorganicsalt of zirconium and palmitic'acid in the ratimof 1 mol of ZrO: to '2 mols of said acid at temperatures suflicient to melt said acid, then ad gan'alkali solution with stirring, cooling the resulting alkaline mix and; neutralizing same to acid with pre ipita .tion of solid material, and finally washlng'an'd dewat ering said solid material to form' the anhydrous zirconyl palmitate.
4. Themethod of preparing zirconyl'oleate which comprises mixing an aqueous solution of a water-soluble inorganic salt of zirconium and oleic acid in the ratio of 1 mol of ZrOa to 2 mols of said acid at temperatures sufficient to melt said'acid, then adding an alkali solution with stirring, cooling the resulting alkaline mix and neutralizing same to acid with precipitation of solid material, and finally washing and dewatering said solid material to form the anhydrous zirconyl oleate.
5. In the production of zirconium salt of a water-insoluble fatty acid, the step which consists in mixing an aqueous saponified solution of said acid with a water-soluble inorganic salt of zirconium in the ratio of 1 mol of ZrOz to 2 mols of said acid at temperatures between 50 C. and 75 C. Y
6. In the production of a zirconyl stearate, the step which consists in mixing an aqueous saponified solution ofstearic acid with a water-soluble inorganic salt of zirconium in the ratio of 1 mol of ZIO: to 2 mols of said acid at temperatures between 50 C. and 75 C.
7. In the production of a zirconyl palmitate, the step which consists in mixing an aqueous saponi-' fled solution of palmitic acid with awater-soluble inorganic salt of zirconium in the ratio of 1 mol of ZrOz to 2 mols of said acid at temperatures" between 50 C. and 75 C.
8. In the production of a zirconyl oleate, the step which consists in mixing an aqueous saponified solution of'oleic acid with a water-soluble inorganic salt of zirconium in the ratio of 1 mol of ZrOz to 2 mols of said between 50 C. and 75 C.
add at temperatures I .9. In the production of a zirconyl stearate from a mixture of an aqueous saponified solution of stearic acid and a water-soluble inorganic salt of of ZrOz to 2 mols of said acid, the step which consists in neutralizing to acid said mixture to precipitate therefrom the zirconyl stearate.
10. In. the production of a zirconyl palmitate from a mixture of an aqueous saponified solution of palmitic acid and a water-soluble inorganic salt of zirconium in the ratio of 1 mol of ZrOz to 2 mols of said acid. the step which consists in neutralizing toacid said mixture to precipitate therefrom the zirconylpalmitate.
11.. In the production of a zirconyl oleate from a mixture of an aqueous saponified solution of oleic acid and a water-soluble inorganic salt of zirconium in the ratio'of 11 mol of ZrOa to 2 mols of said acid, the step which consists in neutralizing to acid said mixture to precipitate therefrom the zirconyl oleate.
' 12. As a new composition of matter, a waterproof fatty acid soap of zirconium of the formula Z1O(RCOO)2 substantially free of RCOOH and water soluble compounds, wherein R represents a higher alkyl radical.
13. As-a new composition of. matter, a waterproof zirconyl stearate of the formula substantially free of stearic acid and water soluble 15. As a. new composition ofmatter, a watercompounds. proof zirconyl palmitate of the formula, 14. As a new composition of matter, a waterzrowmwm) 000) 2 proof zirconyl oleate of the formula bst ti u I f 1 1] id d t su an a y me 0 pa I111 10 ac an wa er 5 ZrO (0113mm) 1CH.CH(CH2) 1000) 2 soluble compounds substantially free of oleic acid and water soluble CHARLES J. KINZIE. compounds. EUGENE WAINER.
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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2417071A (en) * 1943-08-14 1947-03-11 Colgate Palmolive Peet Co Preparation of water-insoluble organic salts
US2457853A (en) * 1944-09-20 1949-01-04 Nat Lead Co Treatment of textiles and composition therefor
US2477116A (en) * 1944-07-18 1949-07-26 John C Cowan Protective coating compositions and methods for producing the same
US2482816A (en) * 1943-06-08 1949-09-27 Nat Lead Co Method of waterproofing textiles with zirconyl compounds
US2739905A (en) * 1952-08-29 1956-03-27 Carlisle Chemical Works Zirconyl 2-ethylhexoate
US2739902A (en) * 1952-08-29 1956-03-27 Carlisle Chemical Works Drier compositions
US2802847A (en) * 1951-08-02 1957-08-13 Nat Lead Co Basic zirconyl soaps and method for preparing the same
US2862014A (en) * 1953-05-28 1958-11-25 Ethyl Corp Organic material
US3036101A (en) * 1959-03-26 1962-05-22 Magnesium Elektron Ltd Production of zirconium soaps
DE977089C (en) * 1952-08-29 1965-02-04 Advance Produktion G M B H Deu Drying agents for paints, varnishes and printing inks
US4148812A (en) * 1975-03-26 1979-04-10 Armour Pharmaceutical Company Method of making basic zirconium-amino-acid gels
US4223010A (en) * 1979-01-08 1980-09-16 Armour Pharmaceutical Company Basic zirconium complexes and methods of making and using in antiperspirants
US4730067A (en) * 1986-02-18 1988-03-08 Akzo America Incorporated Process for the preparation of zirconium carboxylate

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2482816A (en) * 1943-06-08 1949-09-27 Nat Lead Co Method of waterproofing textiles with zirconyl compounds
US2417071A (en) * 1943-08-14 1947-03-11 Colgate Palmolive Peet Co Preparation of water-insoluble organic salts
US2477116A (en) * 1944-07-18 1949-07-26 John C Cowan Protective coating compositions and methods for producing the same
US2457853A (en) * 1944-09-20 1949-01-04 Nat Lead Co Treatment of textiles and composition therefor
US2802847A (en) * 1951-08-02 1957-08-13 Nat Lead Co Basic zirconyl soaps and method for preparing the same
US2739902A (en) * 1952-08-29 1956-03-27 Carlisle Chemical Works Drier compositions
US2739905A (en) * 1952-08-29 1956-03-27 Carlisle Chemical Works Zirconyl 2-ethylhexoate
DE977089C (en) * 1952-08-29 1965-02-04 Advance Produktion G M B H Deu Drying agents for paints, varnishes and printing inks
US2862014A (en) * 1953-05-28 1958-11-25 Ethyl Corp Organic material
US3036101A (en) * 1959-03-26 1962-05-22 Magnesium Elektron Ltd Production of zirconium soaps
US4148812A (en) * 1975-03-26 1979-04-10 Armour Pharmaceutical Company Method of making basic zirconium-amino-acid gels
US4223010A (en) * 1979-01-08 1980-09-16 Armour Pharmaceutical Company Basic zirconium complexes and methods of making and using in antiperspirants
US4730067A (en) * 1986-02-18 1988-03-08 Akzo America Incorporated Process for the preparation of zirconium carboxylate

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