US3723152A - Drying oil compositions cobalt drier compositions therefor and process of making same - Google Patents

Drying oil compositions cobalt drier compositions therefor and process of making same Download PDF

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US3723152A
US3723152A US00093388A US3723152DA US3723152A US 3723152 A US3723152 A US 3723152A US 00093388 A US00093388 A US 00093388A US 3723152D A US3723152D A US 3723152DA US 3723152 A US3723152 A US 3723152A
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cobalt
acid
metal
drier
compositions
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A Alkaitis
G Thomas
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Mooney Chemical Inc
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Mooney Chemical Inc
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/126Acids containing more than four carbon atoms
    • C07C53/128Acids containing more than four carbon atoms the carboxylic group being bound to a carbon atom bound to at least two other carbon atoms, e.g. neo-acids
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D191/00Coating compositions based on oils, fats or waxes; Coating compositions based on derivatives thereof
    • C09D191/005Drying oils
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09FNATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
    • C09F9/00Compounds to be used as driers, i.e. siccatives

Definitions

  • These salts have an amount of metal such that the sum of the stoichiometric amount of the metal and the excess corresponds to at least about 115% of the amount for neutralization of the acid by cobalt metal.
  • the process used to make such salt reacts an excess of the metal with the acid in the presence of water and oxygen-containing gas for a time longer than required to neutralize the acid with metal. Then Water is removed.
  • This invention relates to drying oil compositions containing cobalt and to drier compositions containing basic cobalt salt of neoalkanoic acid and relates also to the process of the manufacture of such basic cobalt salt.
  • a paint is defined in The Condensed Chemical Dictionary, Sixth edition, published in 1961 by Reinhold Publishing Corp., New York, NY. as a liquid mixture which may be applied to surfaces to form a dry, thin, protective or decorative film. Some paints are referred to as enamels. Some enamels based on tall oil alkyds are referred to as short oil alkyd enamels, medium oil alkyd enamels or long oil alkyds.
  • varnish as an unpigmented oil-base paint composed of a solvent and either of two types of binders.
  • One type of binder forms a film by oxidation or polymerization, such as drying oils alone or in combination with other materials such as natural or synthetic resins.
  • the other type of binder forms films by evaporation of the solvent, such as shellac and alkyd varnishes.
  • Some varnishes are formulated such that they are applied as hot spray.
  • the temperature of the varnish is illustratively 150 F.
  • drying oil composition refers to pigmented paints containing drying oil and to varnishes containing drying oil, such as mentioned above.
  • the primary function of a drier in paints and varnishes i.e., drying oil compositions, is to accelerate the oxidation of the unsaturated oil and so speed up the drying of the paint film.
  • Cobalt sulfate is listed as the cobalt compound used and there is described a precipitation process for making cobalt naphthenate from this cobalt compound and sodium naphthenate obtained by reacting naphthenic acid with caustic soda aqueous solution.
  • the reactions are presented on page 35 of the book, where it is indicated that the amount of cobalt sulfate is slightly less than the stoichiometric amount required to react with sodium naphthenate.
  • the cobalt naphthenate is a neutral salt.
  • the cobalt naphthenate product is thinned with white spirit, i.e., mineral spirits which is a narrow-boiling-range fraction of petroleum with a boiling range between about 200 F. and about 300 F.
  • white spirit i.e., mineral spirits which is a narrow-boiling-range fraction of petroleum with a boiling range between about 200 F. and about 300 F.
  • the conventional diluted drier composition contains 6% by weight of cobalt metal.
  • -M0re concentrated drier compositions have been prepared, but the viscosities of such compositions are too great for convenient use in the formulation of drying oil compositions.
  • driers as chemical additives used to accelerate the drying period of paints, varnishes, printing inks and the like by catalyzing the oxidation of drying oils or synthetic resin varnishes, such as alkyds, which dry by air curing.
  • Page 45 of the book by the Oil and Colour Chemists Association presents the percentage of metal introduced as metal salt of organic carboxylic acids, such as naphthenic acids, incorporated in various types of paints, varnishes and alkyds. These metals are cobalt, lead and manganese.
  • calcium metal as calcium salt is also present or is optionally present.
  • Lead naphthenate as a commercial product, has been made to contain 24% by weight of lead metal, Whereas cobalt and manganese naphthenates, as commercial drier compositions, contain 6% by weight of metal.
  • the use of lead drier is such as to provide a substantially larger Weight percentage of metal than the weight percentage of cobalt.
  • the use of the drier composition of cobalt naphthenate with 6% by weight of cobalt and the lead naphthenate drier composition containing 24% by weight of lead metal has permitted easy formulation of drying oil compositions as paints, varnishes and alkyds because of this 4:1 ratio of metal content, i.e., lead to cobalt, permitting the use of their drier compositions in relative amounts that represent for both whole numbers in many cases.
  • cobalt drier composition One recently available cobalt drier composition has been examined and found to contain 12.01% by Weight of cobalt.
  • This cobalt drier composition contains a cobalt salt of neodecanoic acid and thus is designated 12% Cobalt Neodecanoate.
  • This drier composition has an acid number of +5. It had a high measured Gardner viscosity of at 25 C., which is convertible to a viscosity of 3.70 poises using the table on page 56 of the book entitled Paint and Varnish Manual Formulation and Testing by Philip L. Gordon and Ruth Gordon, published in 1955 by Interscience Publishers, Inc., New York, NY.
  • U.S. Pat. No. 2,409,678 of C. H. Hamblet describes and claims a process for the preparation of heavy metal salts of organic acids, such a naphthenic acid and long chain fatty acids.
  • the process uses heavy metals. Lead, copper and zinc are among the heavy metals expressly mentioned.
  • an organic acid is converted to the corresponding metal salt by direct contact with the metal in the presence of oxygen.
  • the process of the patent is concerned with the prevention of degradation of the organic acid during the reaction in the presence of antioxidant. That patent refers to two other patent applications which have become U.S. Pats. Nos. 2,395,307 and 2,416,074, filed by A. G. Weber and C. H. Hamblet.
  • U.S. Pat. No. 2,528,803, granted to G. G. Unkefer discloses a process utilizing the reaction of a heavy metal with an organic carboxylic acid, such as naphthenic acid and 2-ethylhexoic acid, in which the reaction is accelerated by the presence of two types of materials, one of which is a low molecular weight organic carboxylic acid, such as acetic acid.
  • the other material is an alcohol.
  • the process does not require the presence of water but it may be present. It is stated that the advantage of not adding water is that drying of the product is not necessary.
  • the acetic acid would increase the rate of reaction because it is a stronger acid than the higher molecular weight acids, such as naphthenic acid and 2-ethylhexoic acid.
  • Example 18 describes the preparation of lead naphthenate
  • Example 19 describes the preparation of basic lead naphthenate. Both are indicated as being useful as drier compositions.
  • the preparation of basic lead naphthenate is not surprising in View of the fact that lead is an amphoteric chemical element.
  • salts of the organic carboxylic acid and of other metals are prepared as neutral salts. Some are somewhat acidic due to the use of the organic acid in an amount slightly greater than stoichiometric.
  • Neodecanoic acid is described as a branch-chain aliphatic monobasic acid derived from petroleum.
  • This organic carboxylic acid has two methyl groups attached to the carbon atom immediately adjacent to the carboxyl group so that molecular structure of neodecanoic acid is represented by the formula:
  • R represents various branched alkyl groups containing 6 carbon atoms.
  • the carbon adjacent to the carboxyl group is a diamond carbon atom because it has four carbon atoms attached to it.
  • the generic term for such molecular structure is neonalkanoic acid.
  • the compounds defined by the term neodecanoic acid are neoalkanoic acids containing branching beyond the diamond carbon atom.
  • Neodecanoic acid as a commercial product contains a small amount of branch-chain aliphatic monobasic acids containing 9 atoms and 11 carbon atoms with this neoalkanoic acid structure.
  • Neodecanoic acid has been recommended in that bulletin for possible use in the form of cobalt, manganese and lead soaps, as driers.
  • This neodecanoic acid has been used to prepare the cobalt neodecanoate drier composition containing a theoretical 6% by weight of cobalt.
  • the preparation of this drier has been described by Enjay bulletin ECL 6605 1448 as follows:
  • Neodecanoic acid (206.4 gm.; 1.2 mole) is reacted with 1140 ml. of 1 N sodium hydroxide in a 4-liter beaker at 60 C. The solution is then diluted to 1600 ml. with distilled water. Baker Reagent cobalt chloride hexahydrate (142.8 gm.; 0.6 mole) in 1 liter of warm (50 C.) distilled water is added slowly with stirring to the sodium salt solution. A deep blue drier forms immediately and, after addition of all the cobalt chloride solution, 260 gm.
  • ISOPAR K an odorless mineral spirits made synthetically and constituting a mixture of isoparafiin hydrocarbons that are highly branched with a boiling range between about 345 and 410 F.
  • ISOPAR K an odorless mineral spirits made synthetically and constituting a mixture of isoparafiin hydrocarbons that are highly branched with a boiling range between about 345 and 410 F.
  • U.S. Pat. No. 2,116,321 discloses an ink drier embodying a basic cobalt salt of naphthenic acid of high, e.g., 18% by weight, cobalt metal content. These salts are solids rather than liquids and are mentioned as being substantially insoluble in oil. The procedure, by which this basic cobalt salt of naphthenic acid is made, is described in that patent. An aqueous solution of cobalt sulfate is added to an aqueous solution of sodium naphthenate, obtained from caustic and naphthenic acid and containing an excess of caustic. A blue precipitate is formed.
  • U.S. Pat. No. 2,955,949 discloses a process of making trialkyl acetic acids, i.e., neoalkanoic acids such as neodecanoic acid and paint driers of their lead, cobalt and manganese salts. It discloses a column 5, lines 50-54, that such acids readily form basic salts with cobalt, manganese and lead.
  • the only description of a process of making a cobalt salt of trialkyl acetic acids is the precipitation method. Apparently this is the process used to make basic cobalt salt, i.e., make a salt that doesnt require excess acid.
  • Enjay Co., Inc. an affiliate of the assignee of that patent, has described in the more recent report mentioned above the preparation of oilsoluble cobalt neodecanoate in which the stoichiometric double decomposition action is followed by the addition of a small amount of neodecanoic acid to provide a composition of the salt in the mineral spirits that is stabilized by the acid against sludging.
  • Some of the objects of the present invention are to provide a cobalt drier composition:
  • a cobalt salt is oil-soluble and contains cobalt and neodecanoate groups in proportions such as to reduce the cost of manufacture as compared with neutral or acidic salt of those groups;
  • the cobalt salt is oil-soluble and the drier composition contains about 12% by weight cobalt metal content to reduce shipping costs but also has a satisfactorily low viscosity to provide ready dissolution in the making of paint formulations and the like due to the low viscosity of the drier composition.
  • Another object of this invention is to provide drying oil compositions containing cobalt drier in an oil-soluble form as a salt in which the organic acid content is less on a stoichiometric basis than in oil-soluble salts used heretofore.
  • the present invention as a process reacts cobalt metal with neodecanoic acid, as the relatively pure material or as the commercial product that contains minor amounts of the C and C trialkyl acetic acids, in the presence of air or other oxygen-containing gas and in the presence of water, at an elevated temperature, such as between about 140 F. and about 280 F., preferably between about 170 F. and about 190 F. while mixing the acid and granular cobalt metal.
  • the mixture contains mineral spirits or similar material that dilutes the acid.
  • the mixture preferably uses a small amount of acetic acid, which can be added with the water as a dilute acetic acid aqueous solution, to accelerate the rate of reaction between the metal and the neodecanoic acid. This mixing of the ingredients can :be carried out under conditions where there is some loss of volatile material, but this loss can be overcome by periodic addition, if desired, of mineral spirits or other suitable solvent.
  • the process of the invention as described in the preceding paragraph is a conventional process.
  • the former uses relative amounts of the neodecanoic acid and the metal and a sufiicient time and temperature of reaction that at least 105% preferably at least 115% of the neodecanoic acid is neutralized by reaction with the cobalt metal.
  • This degree of neutralization of the acid is a reaction that actually prepares a basic cobalt neodecanoate in which the term basic as used in this specifications description of the invention and in the claims refers to the alkalinity or basicity of the salt.
  • This degree of neutralization for a drier composition of the invention containing the salt in a concentration to provide 12% by weight of cobalt metal can be expressed by a negative value for acid number, and such values of acid number can range between about 30 and about -70, preferably between about -30 and about -60.
  • acid number has the conventional meaning, namely, the milligrams of potassium hydroxide required to neutralize one gram of a sample of such material having the stated acid number.
  • the percent of neodecanoic acid neutralized is a term used to express alternatively the basicity. It expresses also the relative amounts of cobalt metal and of the neodecanoate group combined in the oil-soluble product having this substantial degree of basicity.
  • the starting mixture for the reaction may be added to a reaction vessel having a reflux condenser to reduce substantial loss of volatile materials during the reaction.
  • the mixing can be provided by mechanical means, but sufficient air or other oxygencontaining gas must be introduced into the mixture of reactants because oxygen participates in the overall reaction.
  • the air may be introduced in a manner to provide the intimate mixing of the ingredients.
  • the liquid material is being intimately mixed with the metal.
  • This mixture during the reaction is at an elevated temperature as mentioned above.
  • the reaction mixture is cooled to room temperature after the reaction has proceeded to the extent that the percentage of acid neutralized that is attained in carrying out the process of the present invention, the reaction mixture is non-homogeneous.
  • this reaction product after heating to a high enough temperature for removal of water, becomes a liquid that remains homogeneous even when cooled to room temperature.
  • the percent acid neutralized of the reaction product after water removal is at least 105 and preferably much higher.
  • Theminimum basicity expressed as 105% of neodecanoic acid neutralized, is stated above.
  • the maximum percentage of acid neutralized by cobalt is determined by the amount of basicity to be provided without losing the requisite oil solubility.
  • This basic cobalt neodecanoic salt has been made by the process with as high a basicity as 146% neodecanoic acid neutralized.
  • the basicity he a maximum of about 135% neodecanoic acid neutralized.
  • salts are such that by suitable dilution with the mineral spirits or other solvents, particularly hydrocarbon solvents, there can be provided a drier composition containing 12% by weight of cobalt.
  • This composition has a low viscosity and thus permits ready mixing of it into drying oil compositions.
  • the reaction product obtained by the process of this invention contains a stoichiometric excess of cobalt relative to the organic acid, i.e., contains more cobalt than would be present in a neutral cobaltous salt of this acid. This excess is expressed by the minimum value of 105% neodecanoic acid neutralized that is expressed above.
  • This value can be expressed as 5% basicity for the product which is termed basic cobalt neodecanoate. It is preferred that the percent of neodecanoic acid neutralized in the product of the process be at least 115, i.e., it is preferred that the product be at least 15% basic. In view of the fact that the higher the percent basicity, the greater the saving and cost of starting materials due to the lessened content of neodecanoic acid radical, it is most desirable to provide as the product of the invention the basic cobalt neodecanoate in which the neodecanoic acid is at least neutralized by cobalt. Of course, there is the upper limit, beyond which the basic cobalt neodecanoate has a composition such that it is not soluble in mineral spirits or other similar liquid ingredients for drying oil compositions and is not soluble in the drying oil com-positions.
  • the drier composition of the invention preferably contemplates compositions in which the degree of basicity is that referred to above.
  • the cobalt metal content is 12% by weight.
  • the degree of basicity is preferably at least 30%.
  • the drier compositions of the present invention can be used to provide the same cobalt metal content for drying oil compositions as the cobalt metal content heretofore included in such compositions by the use of neutral or acidic cobalt salts of other organic acids, such as naphthenic acid and 2-ethylhexoic acid.
  • the drier compositions can be mixed, in any conventional concentration of neutral or acidic cobalt salt, with manganese drier composition, lead drier composition, zirconyl drier composition, or combinations of these.
  • the zirconyl salt is a substitute for lead drier in numerous formulations of drying oil compositions.
  • drier compositions of salts of other metals can be incorporated in the drier composition of basic cobalt neodecanoate of this invention by co-manufacture of such metal salts as neodecanoates in the case of those metals that form the desired salt by reaction of the metal as such with neodecanoic acid.
  • zirconyl salt would not be co-manufactured because it is prepared by a different type of a reaction.
  • the lead or manganese salt of neodecanoic acid also can be separately prepared and then mixed with the basic cobalt salt of drier composition in a desired ratio of the two metals or can be separately supplied for incorporation in the drying oil composition.
  • the following examples illustrate the process of the invention and the drier composition containing basic cobalt neodecanoate, especially as a composition with a 12% cobalt metal content.
  • One example illustrates drying oil compositions containing this basic cobalt neodecanoate in a couple of formulations.
  • EXAMPLE I A 600-gram content of neodecanoic acid was diluted with mineral spirits. A small amount of water and a few drops of acetic acid were added. The mixture was stirred into a vessel containing an excess of granular cobalt. This mixture was blown with air and reacted at 90 F. to 172 F., the latter being the highest temperature reached during the course of the reaction. Samples of the mixture were taken periodically and the organic phase of a sample was titrated to determine its acid number. When a sample by its acid number indicated the completion of the reaction in a stoichiometric sense by having an acid number of zero, the introduction of air and the mixing were ceased. The batch was allowed to cool overnight.
  • the organic phase was sampled and found to be a product having 106% of the neodecanoic acid neutralization, i.e., 6% basic.
  • the rest of the organic phase was reheated to a temperature sufiicient to remove water and some of the mineral spirits.
  • the dehydrated product contained 12.05% cobalt metal and this product contained 118% neodecanoic acid neutralized, i.e., was 18% basic.
  • this dehydrated product was a thin fluid, i.e., a fluid having a low viscosity. Surprisingly this product is soluble in mineral spirits and conventional drying oil compositions.
  • This product has the economic advantages due to its lower content of relatively expensive organic acid and its lowered shipping and handling costs due to its higher cobalt content that reduces the volume of cobalt product shipped to provide a specific content of drier for a given quantity of drying oil composition to be manufactured.
  • EXAMPLE II The reaction of neodecanoic acid with excess of granular cobalt in the presence of mineral spirits as a diluent, with water and acetic acid as catalyst and with the mixture being blown with air at an elevated temperature, was performed with samples being taken at regular intervals and titrated for acid number. The reaction proceeded to the extent that it was indicated by the acid number that the acid was more than neutralized. However, the degree of basicity appeared to reach a maximum value of 10% even though the reaction was conducted for a prolonged period of time. The samples solidified when permitted to cool.
  • EXAMPLE III A further study of the reaction under conditions similar to the reaction performed in Example II provided a dehydrated fluid product containing 12% by weight of cobalt metal basic cobalt neodecanoate having a basicity of 35%. Such product was obtained after eight hours of reaction. Periodic samples taken earlier in the course of the reaction and titrated directly, i.e., determined for acid number without water removal, would have indicated that the basicity was remaining constant at a value of 10% over a period of the last four hours of the period during which the course of the reaction was followed.
  • EXAMPLE IV A reaction flask was charged with 750 grams of a technical grade of neodecanoic acid obtained from Enjay Company, Inc. This acid had an acid number of 318. This acid was diluted with 750 grams of mineral spirits. To this mixture, 200 grams of 2.5% acetic acid aqueous solution were added. This batch of ingredients was heated to F. Cobalt granules in the amount of 196 grams were added to this batch that had been heated to 180 F. while the batch was being stirred. Air was bubbled into the contents of the reaction flask. Hourly samples of the reaction mixture were taken. The cobalt content of a sample was determined by the method designated ASTM- D-2373. The acid number, positive or negative, was determined by the method described later. From these two values the percent of neodecanoic acid neutralized by the cobalt was calculated, as explained later.
  • the samples were non-homogeneous, as discussed earlier, and only a portion of the sample was utilized to determine the percent acid neutralized by cobalt. Another portion of each was heated to remove water. The dry sample was analyzed for cobalt content and acid number to determine its percent of acid neutralized. The following tabulation presents the results of the present neutralized for each sample, prior to water removal and designated a wet sample, as compared with a sample after water removal and designated a dry sample. The discrepancies and variations are believed to be due to the lack of homogeneity.
  • EXAMPLE V Cobalt metal granules were reacted with neodecanoic acid diluted with mineral spirits in the presence of water and acetic acid with mixing of the reactants and with bubbling of air through the mixture described in earlier examples.
  • Duplicate samples were taken periodically during the course of the reaction. One of the duplicate samples was allowed to settle and the upper layer was analyzed for acid number and cobalt metal content to determine the percent of neodecanoic acid neutralized. The other sample of the duplicate set was heated to 300 F. for dehydration and then analyzed for acid number and co balt content. The following are the values of percent neutralization obtained for the samples.
  • Neodecanolc acid neutralized percent Settled Dehydrated Reaction sample sample hours
  • EXAMPLE VI The following data show the percent acid neutralized for the reaction performed in two difierent runs.
  • the product designated as 1st run had the neodecanoic acid only 113% neutralized by cobalt but the second one had the neodecanoic acid 116% neutralized cobalt. The latter value is within the preferred range of percent neutralized. Five other runs provided percent of neutralization of 123, 117, 116, 108 and 119% for the dehydrated product.
  • drier composition containing basic cobalt neodecanoic having 146% neodecanoic acid neutralized by cobalt and with a cobalt content by weight of about 12% in the drier composition has been obtained.
  • EXAMPLE VII This example illustrates the use of the drier composition of the invention in drying oil compositions of the present invention and provides a comparison with conventional cobalt salts heretofore available.
  • Enamel compositions percent by weight Medium 01 1 Long oil Enamel ingredients soya alkyd linseed alkyd Titanium dioxide.-. 30.12 xid 2. 57 48. 99 0. 35 17. 97
  • the Beckosol products shown above are the alkyd resins.
  • Nuosperse is a dispersing agent.
  • Varsol is a well-known type of hydrocarbon solvent.
  • the Enjay bulletin that describes the preparation of 6% cobalt neodecanoate is mentioned above, having a plus value for acid number. That description indicates that 585 lbs. of neodecanoic acid would be treated with lbs. of cobalt to produce this cobalt salt that is slightly acidic.
  • the present invention provides a reaction in which the ingredients are present in a different proportion such that the reaction product is that produced by reaction of 100 lbs. of cobalt with as small amount as 433 lbs. of neodecanoic acid. In view of the fact that 1 lb. of the basic cobalt neodecanoate drier composition of the present invention containing 12% cobalt can be used in place of 2 lbs.
  • potassium oxalate solution is a saturated solution ob tained by adding 700 grams of potassium oxalate to 2 liters of distilled water with heating of the mixture until the salt is dissolved followed by cooling.
  • the mixture of sample, carboxylic acid solution, methanol and potassium oxalate aqueous solution is heated with stirring to the boiling point and then removed from the heat. After adding 1 ml. of a 1% alcohol solution of phenolphthalein, the solution is titrated with standardized 1 N sodium hydroxide aqueous solution.
  • the acid number mg. of KOH per gram of sample, is calculated as follows:
  • the quantity of excess or basic cobalt is expressed as 50 milligrams (as KOH) per gram of sample. This is expressed as equivalents of cobalt per 100 grams of sample as follows:
  • the equivalents of acid which have been neutralized are therefore The percentage of acid neutralized by cobalt is The basicity is When the product is concentrated to 12% Co by removal of solvent, the acid number is increased to 60.
  • This basicity percentage is an expression of the percentage, by weight or by equivalents, of cobalt in the basic cobalt salt that is in excess of the cobalt content of a neutral cobalt salt of the organic acid, i.e., cobaltous salt of the organic acid in which one-half of the formula weight of cobalt is combined with the formula weight of the anion of the organic monocarboxylic acid.
  • a sample of the 12% basic cobalt neodecanoate drier composition of the present invention is compared below with a sample of a recently obtained 12%. acidic cobalt neodecanoate.
  • the basic cobalt neodecanoate drier of the invention had an acid number of 37, a non-volatile material content of 66% with an A-2 Gardner viscosity at 25 C. (0.220 poise) whereas the acidic cobalt salt had an acid number of +5, a non-volatile material content of 75% by weight and an 0 Gardner at 25 C. (3.70 poises).
  • Neo- Decanoic Acid The Enjay bulletin of January 1960, on neodecanoic acid and designated MD-238 refers to this acid as Neo- Decanoic Acid. It indicates the following values for a typical inspection.
  • a process of preparing a drying oil soluble composition that contains about 12% cobalt as a product from the reaction of cobalt metal and neodeconoic acid and that remains homogeneous even when cooled to room temperature which consists essentially of:
  • cobalt metal being present in an amount that is at least of the stoichiometric amount that would be present in neutral cobaltous neodecanoate obtainable from all of said neodecanoic acid;
  • neodecanoic acid is a technical grade in which in addition to neodecanoic acid having the formula:
  • R represents various branched alkyl groups containing six carbon atoms, such acid contains minor percentages of similar trialkyl acetic acids containing 9 and 11 carbon atoms
  • the temperature of reaction is F.
  • the acetic acid and water were present by the use of a 2.5% by weight acetic acid aqueous solution, wherein, on weight basis, the initial mixture contains 750 parts each of the neodecanoic acid and mineral spirits, 196 parts of cobalt granules, 200 parts of said acetic acid solution, and wherein the total reaction is carried out for 12 hours followed by cooling with separation into layers and with separation of the upper phase containing the cobalt neodecanoate and treatment of that phase for the dehydration followed by the adjustment of mineral spirits content.
  • a composition prepared by the process of claim 1. A composition prepared by the process of claim 2. 8. A composition prepared by the process of claim 3. 9. A composition prepared by the process by claim 4. 10. A composition prepared by the process of claim 5.

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3941606A (en) * 1971-07-20 1976-03-02 Mooney Chemicals, Inc. Metal carboxylate-alkoxy alcoholate composition and process
US4311625A (en) * 1980-11-10 1982-01-19 Tenneco Chemicals, Inc. Water-borne surface-coating compositions containing complexed cobalt driers
EP0058792A1 (de) * 1981-02-17 1982-09-01 Nuodex Inc. Verfahren zur Herstellung von öllöslichen Metallsalzen
US4374777A (en) * 1981-04-09 1983-02-22 The United States Of America As Represented By The Secretary Of The Navy Synthesis of hydrocarbon soluble vanadium catalyst
FR2575745A1 (fr) * 1985-01-09 1986-07-11 Charbonnages Ste Chimique Savons de cobalt oleosolubles
EP0188115A1 (de) * 1984-12-18 1986-07-23 Mooney Chemicals, Inc. Herstellung von Zusammensetzungen der Übergangsmetallsalze von organischen Carbonsäuren
US5141562A (en) * 1991-06-21 1992-08-25 Mooney Chemicals, Inc. Drier promoter compositions
US5156674A (en) * 1991-06-21 1992-10-20 Mooney Chemicals, Inc. Drier promoter compositions

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3941606A (en) * 1971-07-20 1976-03-02 Mooney Chemicals, Inc. Metal carboxylate-alkoxy alcoholate composition and process
US4311625A (en) * 1980-11-10 1982-01-19 Tenneco Chemicals, Inc. Water-borne surface-coating compositions containing complexed cobalt driers
EP0058792A1 (de) * 1981-02-17 1982-09-01 Nuodex Inc. Verfahren zur Herstellung von öllöslichen Metallsalzen
US4374777A (en) * 1981-04-09 1983-02-22 The United States Of America As Represented By The Secretary Of The Navy Synthesis of hydrocarbon soluble vanadium catalyst
EP0188115A1 (de) * 1984-12-18 1986-07-23 Mooney Chemicals, Inc. Herstellung von Zusammensetzungen der Übergangsmetallsalze von organischen Carbonsäuren
FR2575745A1 (fr) * 1985-01-09 1986-07-11 Charbonnages Ste Chimique Savons de cobalt oleosolubles
US5141562A (en) * 1991-06-21 1992-08-25 Mooney Chemicals, Inc. Drier promoter compositions
US5156674A (en) * 1991-06-21 1992-10-20 Mooney Chemicals, Inc. Drier promoter compositions

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