US2456824A - Oil-soluble drier metal salt compositions - Google Patents

Oil-soluble drier metal salt compositions Download PDF

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US2456824A
US2456824A US682586A US68258646A US2456824A US 2456824 A US2456824 A US 2456824A US 682586 A US682586 A US 682586A US 68258646 A US68258646 A US 68258646A US 2456824 A US2456824 A US 2456824A
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oil
drier
metal
viscosity
acid
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Fischer Alfred
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Nuodex Products Co Inc
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Nuodex Products Co Inc
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/126—Acids containing more than four carbon atoms
    • C07C53/128—Acids 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C07C57/12—Straight chain carboxylic acids containing eighteen carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • 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
    • C09F9/00—Compounds to be used as driers, i.e. siccatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C10M2207/126—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/16—Naphthenic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/18—Tall oil acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/061—Metal salts
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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    • C10N2010/00—Metal present as such or in compounds
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Definitions

  • This invention relates to oil-soluble metal salt compositions useful in several arts for various purposes, such, for example, as in connection with paint and varnish driers, bodying agents, cat-v alysts, lubricant additives, etc.
  • the oil-soluble salts of diverse organic acids are in use for many different purposes.
  • the drying metal salts that is, principally lead, cobalt, manganese, iron, zinc and nickel salts of certain organic acids; for example, naphthenic acids, tall oil acids, rosin acids, linseed acids, 2-ethylhexoic acid, etc.
  • naphthenic acids for example, tall oil acids, rosin acids, linseed acids, 2-ethylhexoic acid, etc.
  • the lead salts of certain acids such as naphthenic acids, are employed not only as driers, but also to impart certain desirable characteristics to lubricants.
  • Heavy metal and alkali earth metal salts are generally water-insoluble. Their commercial utility depends upon their ability to dissolve in and to be stable in the organic solvents and vehicles for which they are intended. For example, in the case of cobalt, manganese and lead driers they are usually employed in compositions containing drying oils such as linseed oil. In order that they may function properly it is necessary that they be soluble in such oils and many other types of vehicles used in paints, varnishes and printing inks. Similarly a copper salt, intended for use in fungicides, should be soluble in certain organic vehicles, such as creosote oils, with which it is often associated in fungicidal compositions. Zinc salts, such as zinc naththenate, are employed commercially as wetting agents in paints and varnishes. For such application it is desirable that these salts be 301- uble in the vehicles of such compositions.
  • the metal salts are sometimes employed in solid form; i. e., in the absence of a solvent, but more often they are employed in the form of concentrated liquid solvent solutions.
  • serious difficulties have been experienced in the commercial use of the above described metal salts because they lack the necessary element of solubility. Equally serious troubles are experienced in the preparation of such metal salts and their solutions.
  • metal salts are often only incompletely soluble in solvents which are intended for the preparation of their concentrated solutions, as Well as in the ultimate vehicles and compositions for which they are intended.
  • the solvent solutions generally contain, for the purpose of minimizing their tendency towards sludging and their lack of solubility, relatively high proportions of organic acids. They may carry as much as 25% of free acids for this purpose. This means that a relatively high amount of extraneous matter is introduced along with the active principal. It also means that, were it not for the presence of such free acid, the concentration of the metal salt in such solutions would be increased.
  • alkyl acid phosphates greatly reduce the viscosity of solutions of oil-soluble metal salts and greatly improve the stability and solubility of such solutions. Furthermore, they make it possible to effect considerable economies in the preparation of such compositions.
  • stabilizing agents are of very low vapor pressure and thus will remain permanently associated in the compositions in which they are incorporated.
  • the amount of stabilizing agent needed is relatively small, as low as 25% per total weight of the heavy metal salt solutions having effected markedchanges, but it may be found desirable in some cases to use considerably higher percentages of such stabilizing agents. Generally speaking, we have found that from 1% to 3% produces commercially satisfactory results.
  • alkyl acid phosphates of this invention are compounds with the general formula R-H2PO4 or R-R-HPO4, as well as combinations of both.
  • R" represents an alkyl radical.
  • EXAMPLE 1 In this example a manganese naphthenate has been prepared without the agent of this invention, but employing approximately of free naphthenic acid so as to make the product commercially acceptable. mineral spirits solution of manganese naphthenate carrying 6% manganese metal.
  • the mixture After agitation, the mixture is allowed to stratify into an upper mineral spirits layer containing manganese naphthenate and a lower aqueous layer. The latter is run off and the uper mineral spirits layer is dried in vacuo. The final dry product is adjusted with mineral sprits so that the manganese content is 6%.
  • the product of this example represents the best commercial grade that could be produced prior to this invention.
  • EXAMPLE 3 This example shows the addition of butyl acid phosphate to an already prepared manganese naphthenate drier solution carrying 6% manganese metal.
  • butyl acid phosphate is incorporated into a commercial 6% manganese naphthenate liquid drier.
  • the commercial product is considerably improved. Its viscosity is reduced from 300 cps. to 100 cps.
  • the alkali refined linseed oil solubility which was fair becomes excellent.
  • the original product is rendered stable to heating; that is, the viscosity (100 cps.) and the alkali refined linseed oil solubility (excellent), remain unaffected after heating at 320 F. for three hours.
  • EXAMPLE4 This example shows the addition of octyl acid phosphate to an already prepared manganese naphthenate drier solution carrying 6% manganese metal.
  • octyl acid phosphate 2.5% octyl acid phosphate is incorporated into a commercial 6% manganese naphthenate liquid drier.
  • the commercial product is considerably improved. Its viscosity is reduced from 300 cps. to 100 cps.
  • the alkali refined linseed oil solubility which was fair, becomes excellent.
  • the original product is rendered stable to heating; that is, the viscosity (100 cps.) and the alkali refined linseed oil solubility (excellent), remain unaffected after heating at 320 F. for 3 hours.
  • EXAMPLE 5 This example shows the use of propyl acid phosphate as a stabilizer in a manganese naphthenate solutionin mineral spirits carrying 6% manganese metal.
  • EXAMPLE-7 This example shows the use of but-yl acid phosphate in reducing the viscosity of a Xylol solution of calcium naphthenate carrying 5% calcium metal. 7 I
  • butyl acid phosphate is added to a commercial 5% calcium naphthenate solution.
  • the viscosity is reduced from 37 seconds to seconds at 80 F. on a Gardner-Parks mobilometer with a 200 gram load.
  • EXAMPLE 8 In this example a commercial grade of a Xylol solution of the calcium salt of Z-ethylhexoic acid was first prepared. The solution carried 5% oi calcium metal in the form of the salt. The solution thus made showed an initial viscosity of 34:0 cps. at 80 F. There was then added to this solution 3% by weight of the propyl acid phosphate. The viscosity of the calcium salt solution was reduced down to cps.
  • EXAMPLE 9 A commercial grade of a copper oleate paste in creosote oil was first prepared so as to carry 7% of copper metal. To this paste was then added 3% by weight of. amyl acid phosphate. The viscosity of the composition which, before the addition, was 4630 cps, dropped, after the addition, to 435 cps.
  • EXAMPLE 10 A commercial grade of cobalt linoleate of 9% cobalt metal content, was first prepared by fusion of cobalt acetate and linseed oil fatty acids by standard commercial procedure. The end product was then introduced into linseed oil (which required heating and agitating), so as to provide 2% cobalt metal content in the linseed oil. The dilution of the cobalt linoleate thus prepared showed serious instability after several days standing. There were some discrete particles of the cobalt drier which had separated away from the oil and overall gelation had begun.
  • EXAMPLE'12 A commercial grade of lead linoleate drier was modified through the addition of 3% of octyl acid phosphate. It was found that thismodificatiori showed greatly improved stability characteristics in various drying vehicles as compared with the unmodified material.
  • EXAMPLE 13 A batch of aluminum oleate .was modified through the addition of 1% of amyl acid -phosphate. When dilutions of the aluminum soaps in benzol were made so as to carry 10% of the aluminum soaps, it was found that theviscos'ity of the dilution of the modified soap showed a vis cosity of only 50 cps. By contrast, the dilutionof the unmodified soap was a viscous gel. 1
  • EXAMPLE 14 A manganese drier solution in mineral spirits;- carrying 8% manganese metal, was prepared from a combination of naphthenic acid and- 2 ethylhexoic acid. These acids were used in equal weight proportions in the preparation of To a portion of the drier thus'prepared, 2% of isopropyl acid phosphate was added.- The change in characteristics of the drier are shown in Table 1.
  • Table 1 Modified with 2% isopropyl acid Unmodified phosphate 7 Storage Stability Stableindcfinitcly. Gels within a few days. Viscosity in Ops. at 50. 550. Y Alkali Refined Linseed Oil Excellont..n. Poor.
  • EXAMPLE 15 A typical combination drier comprising lead' and cobalt was first prepared.
  • This drier representing a linseed oil-rosin solution of lead and cobalt linoleate, carried, respectively, 1% cobalt metal and 4% lead metal.
  • To a portion of this drier was then added 3% of isopropyl acid phos phate.
  • the drier thus modified was clear and stable on long storage, whereas the unmodified drier showed considerable sludging and instability on aging.
  • EXAMPLE 16 To a mineral spirits solution of a commercial grade of copper oleate carrying 7% copper metal, was added 1.5% each of amyl acid phosphate and isopropyl acid phosphate. The modified solution showed a viscosity of only 400 cps. By contrast the unmodified solution showed a viscosity of over 4000 cps.
  • I EXAMPLE 18 A commercial rade of an iron tallate catalyst was prepared in the usual manner. The end product carried 8% iron metal. To a portion of this end product, there was then added of butyl'acid phosphate. The unmodified, as well as the modified catalyst were then introduced into typical core oil compositions. It was found that the modified catalyst possessed much better solubility-and compatibility with the core oil than the unmodified catalyst.
  • EXAMPLE 19 The zinc salt of 2-ethylhexoic acid was first prepared by a fusion of zinc oxide and Z-ethylhexoic acid. The end product was then dissolved in a hydrogenated petroleum solvent sold under the name Solvesso #1 by the Standard Oil Company of New Jersey and consisting of a mixture of approximately 65% aliphatic hydrocarbons of boiling range 250-350 F. and 35% of methylated monocylic aromatic hydrocarbons. The solution carried 10% of zinc metal. When to this solution, 2% of isopropyl acid phosphate was added, the initially high viscosity of the solution was reduced from approximately 9800 cps. at 80 F. to 3600 cps. It was also determined that the modification greatly improved the solubility and compatibility of the zinc salt in many organic vehicles.
  • composition of matter consisting essentially of an oil-soluble drier metal salt and a les ser amount of an alkyl acid phosphate wherein the alkyl group embodies not more than 8 carbon atoms. 7
  • composition of matter consisting essentially of an oil-soluble drier metal salt and a lesser amount of an amyl acid phosphate.
  • composition of matter consisting .essentially of an oil-soluble drier metal salt of naphthenic acid and a lesser amount of an alkyl acid phosphate wherein the alkyl group embodies not more than 8 carbon atoms.
  • composition of matter consisting essentially of an oil-soluble drier metal salt of naphthenic acid and a lesser amount of an amyl acid phosphate.
  • composition of matter consisting essentially of a water-soluble drier metal salt and a lesser amount of a butyl acid phosphate.
  • composition of matter consisting essen tially of a Water-soluble drier metal salt and a lesser amount of an isopropyl acid phosphate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US682586A 1946-07-10 1946-07-10 Oil-soluble drier metal salt compositions Expired - Lifetime US2456824A (en)

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NL65938D NL65938C (enrdf_load_stackoverflow) 1946-07-10
US23119D USRE23119E (en) 1946-07-10 Oil-soluble dkiek metal salt
US682586A US2456824A (en) 1946-07-10 1946-07-10 Oil-soluble drier metal salt compositions
GB15298/47A GB641168A (en) 1946-07-10 1947-06-10 Oil-soluble metal salt compositions and method of making same

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2565897A (en) * 1951-08-28 Drier compositions
US2599553A (en) * 1950-02-17 1952-06-10 California Research Corp Complex aluminum soap
US2628202A (en) * 1949-09-23 1953-02-10 Leffingwell Chemical Company Soap useful for making lubricating greases
US3238274A (en) * 1960-02-23 1966-03-01 Distillers Co Yeast Ltd Process for curing unsaturated polyesters using a vanadium compound and an acid phosphate ester as catalysts
US4257913A (en) * 1979-09-17 1981-03-24 Tenneco Chemicals, Inc. Stable manganese salt solutions and a process for their production
US4331575A (en) * 1978-04-28 1982-05-25 Tenneco Chemicals, Inc. Drier systems and surface-coating compositions containing same
US4778611A (en) * 1985-05-02 1988-10-18 Herbert Bishop Oil additive process

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2793962A (en) * 1952-09-10 1957-05-28 Mcgean Chem Co Inc Manufacture of metallic soaps useful as driers
GB986731A (en) * 1961-01-31 1965-03-24 Catalin Ltd Foundry moulding process

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2095508A (en) * 1931-03-02 1937-10-12 Ig Farbenindustrie Ag Process of manufacturing naphthenates
US2188951A (en) * 1939-02-08 1940-02-06 Richards Chemical Works Inc Insecticide
US2228668A (en) * 1941-01-14 Drying oil composition
US2308502A (en) * 1940-08-02 1943-01-19 Standard Oil Co Compounded oil
US2322307A (en) * 1939-06-20 1943-06-22 Standard Oil Co California Compounded oil
US2370080A (en) * 1943-02-03 1945-02-20 Atlantic Refining Co Stabilized lubricant composition
US2409774A (en) * 1942-10-08 1946-10-22 Advance Solvents & Chemical Co Drier metal salt and process of making it

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2228668A (en) * 1941-01-14 Drying oil composition
US2095508A (en) * 1931-03-02 1937-10-12 Ig Farbenindustrie Ag Process of manufacturing naphthenates
US2188951A (en) * 1939-02-08 1940-02-06 Richards Chemical Works Inc Insecticide
US2322307A (en) * 1939-06-20 1943-06-22 Standard Oil Co California Compounded oil
US2308502A (en) * 1940-08-02 1943-01-19 Standard Oil Co Compounded oil
US2409774A (en) * 1942-10-08 1946-10-22 Advance Solvents & Chemical Co Drier metal salt and process of making it
US2370080A (en) * 1943-02-03 1945-02-20 Atlantic Refining Co Stabilized lubricant composition

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2565897A (en) * 1951-08-28 Drier compositions
US2628202A (en) * 1949-09-23 1953-02-10 Leffingwell Chemical Company Soap useful for making lubricating greases
US2599553A (en) * 1950-02-17 1952-06-10 California Research Corp Complex aluminum soap
US3238274A (en) * 1960-02-23 1966-03-01 Distillers Co Yeast Ltd Process for curing unsaturated polyesters using a vanadium compound and an acid phosphate ester as catalysts
US4331575A (en) * 1978-04-28 1982-05-25 Tenneco Chemicals, Inc. Drier systems and surface-coating compositions containing same
US4257913A (en) * 1979-09-17 1981-03-24 Tenneco Chemicals, Inc. Stable manganese salt solutions and a process for their production
US4778611A (en) * 1985-05-02 1988-10-18 Herbert Bishop Oil additive process

Also Published As

Publication number Publication date
NL65938C (enrdf_load_stackoverflow)
GB641168A (en) 1950-08-09
USRE23119E (en) 1949-05-31

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