US2692858A - Castor oil lubricating composition - Google Patents

Castor oil lubricating composition Download PDF

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Publication number
US2692858A
US2692858A US221538A US22153851A US2692858A US 2692858 A US2692858 A US 2692858A US 221538 A US221538 A US 221538A US 22153851 A US22153851 A US 22153851A US 2692858 A US2692858 A US 2692858A
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Prior art keywords
tin
castor oil
oil
proportion
nuclei
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US221538A
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Inventor
Evans Elliott Alfred
Elliott John Scotchford
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CC Wakefield and Co Ltd
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CC Wakefield and Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0092—Mixtures
    • 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
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027—Neutral salts thereof
    • 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
    • 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
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/16—Naphthenic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/402—Castor oils
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
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    • C10M2215/064—Di- and triaryl amines
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    • C10M2215/064—Di- and triaryl amines
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    • C10M2215/066—Arylene diamines
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    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
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    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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    • C10M2219/089—Overbased salts
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • This invention consists in improvements in the treatment of castor oiland related materials particularly to inhibit oxidation'and/ or drying, gumming or hardening of such materials.
  • the rate of oxidation of fatty oils depends on the types of fatty acids present and particularly on their degree of unsaturation.
  • the principal constituents of castor oil are the glycerides of ricinoleic acid, a hydroxy-substituted unsaturated fatty acid containing one ethylenic linkage.
  • the oxidation which takes place is almost certainly accompanied by a polymerisation process in which the unsaturated molecules take part.
  • the rate of oxidation and gum formation will, of course, depend on the temperature to which the oil is subjected and the presence of oxidation catalysts.
  • the invention relates not only to castor oil but to related materials such as the esters of ricinoleic acid, e. g., the simple esters of monohydric alcohols and the polyhydric alcohol esters, to lubricants consisting of mixtures of castor oil and mineral oil (comprising a major proportion of castor oil) and to the so-called casterbase greases containing a major proportion of castor oil.
  • the esters of ricinoleic acid e. g., the simple esters of monohydric alcohols and the polyhydric alcohol esters
  • lubricants consisting of mixtures of castor oil and mineral oil (comprising a major proportion of castor oil) and to the so-called casterbase greases containing a major proportion of castor oil.
  • This invention in its'broadest aspect therefore consists of a method of treating an oil of the kind described to inhibit oxidation and gumming which method consists in adding to the oil where R1, R3 and R4 are the same or difierent and are aromatic radicals, and R2 is a condensed aromatic nucleus having at least ten carbon atoms. Any or all of these radicals may be further substituted by alkyl, aryl, hydroxyl or amine groups, although the preferred substituents are hydrocarbon radicals only.
  • Phenyl-s-naphthylamine Phenyl-a-naphthylamine BB-Dinaphthylamine Xylyl-p-naphthylamine H C H3 G? Di(e-naphthyl) -.ps henylene diamine wlgnm Phenothiazine Thio-phenyl-B-naphthylamine (benzonaphthothiazine)
  • amines of the type described are. effective for the purpose, of the present invention, such closely related amines as aand p-naphthylamine.
  • the organic compounds of tin or antimony to be employed in conjunction with the amines already described are. derivatives, of. divalent (stannous) tin or of antimony and may be, the tin or antimony salts or soaps of organic carboxylic acids, organic sulphonic acids, organic dithiophosphoric acids, or the tin or antimony 7 derivatives of phenols, phenol thioethers, or mercaptans.
  • all of such compounds including the derivatives of phenols, phenol thioethers and mercaptans are considered to be salts of organic acidic com- 7 pounds capable of salt formation.
  • Tin laurate Tin oleate Tin naphthenate Tin petroleum sulphonate Tin derivative of p-tertiary amyl phenol thioether Tin derivative of o-stearyl phenol thioether 011E350 0OS-Oo o 0,111 o o Sn Tin salt of ethylene glycol mononaphthenate cresyl dithiophosphate R.COOCHzCHzO S Where R.COOH naphthenic acid.
  • tin compounds do not themselves possess any appreciable antioxidant or gum-inhibiting properties, they cooperate with the aromatic amines of the type described to give inhibition of oxidation over a period of time considerably longer than could be obtained by the use of the amines themselves in comparable proportions.
  • the petroleum sulphonates of tin and antimony are particularly efiective.
  • the aromatic amines used in this invention may be employed in amounts ranging from about 0.1 to about 5.0 per cent and preferably between 0.5 and 2.0 per cent depending on the particular material to be inhibited, and the conditions under which it is to be employed While the tin or antimony compounds may be employed in amounts varying between about 0.05 and 2.0 per cent and preferably between 0.1 and 1.0 per cent. In general the best results are obtained when the amount of tin or antimony compound present does not exceed the amount of amine by weight and preferably the amount of amine employed is at least double the amount of tin or antimony compound.
  • the additives falling within class (6) which may be employed where necessary in conjunction with the additives of classes (a) and (b) comprise the neutral organic phosphite esters of hydroxy-substituted aromatic thioethers and disulphides.
  • phosphite esters are di-(3-carbomethoxy-4-hydroxy phenyl) thioether cresyl phosphite, and the phosphite ester of t-butyl cresol thioether. These materials may be employed in amounts ranging from about 0.2 to about 5.0 per cent and preferably from 0.5 to 2.0 percent.
  • compositions of this invention may be present in the compositions of this invention.
  • viscosity index improvers foam inhibitors, detergents, or ferrous metal corrosion inhibitors.
  • an antioxidant additive effective at high temperatures, along with the additives of the present invention.
  • an antioxidant might be, for example, the metal salt of an organic dithiophosphorio acid or the metal derivative of an alkylated phenol thioether.
  • Lubricating oil compositions typical of those falling within the scope of the present invention are:
  • tin petroleum sulphonate is meant the-Ctin salt of the oil-soluble petroleum sulphonic acids commonly known as mahogany acids.
  • Table 2.-Iests in this table illustrate the range of tin and antimony compounds which may be employed in conjunction with a typical amine.
  • Table 3 Table 3.-Tests in this table illustrate the types of amines which may be employed in carrying out the present invention, in addition to those already Table 4 Approximate time (hours) to- ?g Material inhibited Inhibitors added Incidence Gum of tackiformancss tion 1 Firsts castor oil None 21 28 l PhenyhS-naphthylamine.
  • Copper catalysts were cleaned with carborundum powder and washed in petroleum ether. Lead specimens were flattened, scraped with a special scraper and finally polished by brushing in one direction with file carding before washing in benzene and weighing. After a 2 hour period a further washing in benzene, brushing with a camel hair brush and reweighing was effected. The total corrosion was calculated by adding together the weight losses of the lead specimens after each two-hour period.
  • test-pieces rectangular plates of pure lead 1%" by 1" were mounted vertically just below the surface of the lubricant with the longer axis horizontal. Copper strips, as catalysts, wide and bent into a semicircle 3%" in diameter were placed wholly below the surface of the lubricant and attached by means of vertical copper wires to corks fitted in the beaker covers. Each beaker was also fitted with a thermometer.
  • test No. 2 (lvileau figulres2 tests) In tests 1 and 3 there was a very heavy buildup of soft black gum on the neck of the inlet valve. In tests 2 and 4 theamount of deposit on the inlet valve was extremely light.
  • Oil B was a mineral lubricating oil of viscosity.
  • the method of. rating piston cleanliness was. that adopted by the Co-ordinating Research Council (C. R. C.) in which a perfectly clean piston is given a rating of 10 and a perfectly black piston a rating of zero.
  • a lubricating composition comprising a major proportion of castor oil in which is incorporated a proportion of from 0.05% to 2.0% of a metallic organic compound soluble in castor oil and selected from the group consisting of tin and antimony salts of aliphatic monocarboxylic acids having 12 to 18 carbon atoms, organic sulphonic acids, naphthenic acids, and phenol thioethers and a proportion of from 0.1% to 5.0% of an aromatic secondary amine containing at least three cyclic nuclei, at least two of which nuclei are aromatic nuclei attached directly to the nitrogen atom.
  • a lubricating composition as claimed in claim 1 in which is incorporated a proportion of from 0.2% to 5.0% of a neutral organic phosphite ester of a hydroxy-substituted aromatic thicether.
  • a lubricating composition as claimed in claim 1 in which is incorporated a proportion of from 0.2% to 5.0% of a neutral organic phosphite ester of a hydroxy-substituted aromatic disulfide.
  • a lubricating composition as claimed in claim 1 comprising also a minor proportion of-a further lubricant additive selected from the group consisting of the reaction product of an aldehyde. with a. basic water-soluble amine and the reaction product of a ketone with a basic watersoluble amine.
  • a lubricating composition comprising a major proportion of castor oil in which isv incorporated a proportion of from 0.05% to 2.0 of a castor oil soluble tin salt of an organic. sulphonic acid and a proportion of from 0.1% to 5.0% of an aromatic secondary amine containing at least three cyclic nuclei, at least two of which nuclei,
  • a lubricating composition comprising a major proportion of castor oil in which is incorporated a proportion of from 0.05% to 2.0% of a castor oil soluble antimony salt of anorganic sulphonic acid and a proportion of from 0.1% to 5.0 of an aromatic secondary amine containing at least three cyclic nuclei, at least two of which nuclei are aromatic nuclei attached directly to the nitrogen atom.
  • a lubricating composition comprising a major proportion of castor oil in which is incorporated a proportion of from 0.05% to 2.0% o1- tin petroleum sulphonate and a proportion of from 0.1% to 5.0% of an aromatic secondary amine containing at least three cyclic nuclei, at least two of which nuclei are aromatic nuclei at-' tached directly to the nitrogen atom.
  • a lubricating composition comprising a major proportion of castor oil in which is incor porated a proportion of from 0.05% to 2.0% of antimony petroleum sulphonate and a proportion of from 0.1% to 5.0% of an aromatic sec ondary amine containing at least three cyclic nuclei, at least two of which nuclei are aromatic nuclei attached directly to the nitrogen atom.

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  • Organic Chemistry (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
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US221538A 1950-05-12 1951-04-17 Castor oil lubricating composition Expired - Lifetime US2692858A (en)

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GB11960/50A GB713423A (en) 1950-05-12 1950-05-12 Improvements in or relating to lubricating compositions
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DE (1) DE909243C (de)
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2796400A (en) * 1953-01-28 1957-06-18 Wakefield & Co Ltd C C Lubricating compositions
US2856359A (en) * 1956-07-20 1958-10-14 Texas Co Superbasic alkaline earth metal sulfonates
US2856360A (en) * 1956-07-20 1958-10-14 Texas Co Superbasic alkaline earth metal sulfonates
US2856361A (en) * 1956-07-20 1958-10-14 Texas Co Superbasic alkaline earth metal sulfonates
US2976238A (en) * 1956-12-24 1961-03-21 Castrol Ltd Oil-based compositions

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE602030A (de) * 1960-04-01
CN115584503B (zh) * 2022-10-19 2024-05-17 安徽万磁电子有限公司 降低基材腐蚀的烧结钕铁硼镍铜镍镀层退镀工艺

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1163856A (en) * 1915-08-16 1915-12-14 Walter T Rice Composite lubricating-oil.
US1594983A (en) * 1926-04-20 1926-08-03 Vanderbilt Co R T Oil composition
US2410652A (en) * 1943-09-15 1946-11-05 Shell Dev Compounded lubricating oil
US2440530A (en) * 1944-11-04 1948-04-27 Shell Dev Stabilized organic compositions
GB616881A (en) * 1946-05-27 1949-01-28 Francis Hayward Ayden Improvements in or relating to lubricating compositions
US2472503A (en) * 1945-10-01 1949-06-07 Shell Dev Lubricating oil compositions
US2551124A (en) * 1947-02-27 1951-05-01 Wakefield & Co Ltd C C Lubricating compositions and additives therefor
US2579038A (en) * 1947-12-09 1951-12-18 Wakefield & Co Ltd C C Lubricant composition

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1163856A (en) * 1915-08-16 1915-12-14 Walter T Rice Composite lubricating-oil.
US1594983A (en) * 1926-04-20 1926-08-03 Vanderbilt Co R T Oil composition
US2410652A (en) * 1943-09-15 1946-11-05 Shell Dev Compounded lubricating oil
US2440530A (en) * 1944-11-04 1948-04-27 Shell Dev Stabilized organic compositions
US2472503A (en) * 1945-10-01 1949-06-07 Shell Dev Lubricating oil compositions
GB616881A (en) * 1946-05-27 1949-01-28 Francis Hayward Ayden Improvements in or relating to lubricating compositions
US2551124A (en) * 1947-02-27 1951-05-01 Wakefield & Co Ltd C C Lubricating compositions and additives therefor
US2579038A (en) * 1947-12-09 1951-12-18 Wakefield & Co Ltd C C Lubricant composition

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2796400A (en) * 1953-01-28 1957-06-18 Wakefield & Co Ltd C C Lubricating compositions
US2856359A (en) * 1956-07-20 1958-10-14 Texas Co Superbasic alkaline earth metal sulfonates
US2856360A (en) * 1956-07-20 1958-10-14 Texas Co Superbasic alkaline earth metal sulfonates
US2856361A (en) * 1956-07-20 1958-10-14 Texas Co Superbasic alkaline earth metal sulfonates
US2976238A (en) * 1956-12-24 1961-03-21 Castrol Ltd Oil-based compositions

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CH304394A (de) 1955-01-15
BE503233A (de)
DE909243C (de) 1954-04-15
NL76200C (de)
MY5700007A (en) 1957-12-31
FR1042974A (fr) 1953-11-05
GB713423A (en) 1954-08-11

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