US3210277A - Stabilisation of chlorinated hydrocarbons - Google Patents

Stabilisation of chlorinated hydrocarbons Download PDF

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US3210277A
US3210277A US388720A US38872064A US3210277A US 3210277 A US3210277 A US 3210277A US 388720 A US388720 A US 388720A US 38872064 A US38872064 A US 38872064A US 3210277 A US3210277 A US 3210277A
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chlorinated
lubricating oil
sequestering agent
phenate
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Swift George Edward
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Imperial Chemical Industries Ltd
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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
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/42—Use of additives, e.g. for stabilisation
    • 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
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    • 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
    • C10M2207/028—Overbased salts thereof
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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
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/042—Epoxides
    • 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
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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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
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic 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
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated 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
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • 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
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/08—Halogenated waxes
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2219/089—Overbased salts
    • 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
    • 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
    • C10M2223/042—Metal salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling

Definitions

  • the present invention relates to the stabilisation of chlorinated hydrocarbons. More particularly it relates to the stabilisation of liquid chlorinated long chain paraffinic hydrocarbons for use as oil additives.
  • a stabiliser system comprising a barium, calcium or magnesium alkyl phenate and a sequestering agent.
  • a stabilised lubricating oil additive comprises at least one liquid chlorinated parafiinic hydrocarbon containing 826 carbon atoms per molecule and at least 25% by weight of chlorine, 0.1-5 of a barium, calcium or magnesium alkyl phenate as hereinafter defined and 0.15% of an oil-soluble sequestering agent for heavy metals, the percentages of the said phenate and the said sequestering agent being calculated on the weight of chlorinated paraflinic hydrocarbon.
  • the barium, calcium and magnesium phenates employed in the present invention have in their simplest form the structure:
  • R is hydrogen or an alkyl group containing 1-10 carbon atoms
  • R is an alkyl group containing 1-10 carbon atoms.
  • R will usually be the same as R since such compounds are the more easily prepared.
  • the phenate employed may, however, contain additionally a proportion of sulphur in the form of a single sulphur linkage or a dithio linkage between the two aromatic nuclei.
  • the formulae of such phenates may be represented by the following two structures I and II, such compounds being alternatively known as alkyl phenol sulphides and disulphides:
  • Suitable sequestering agents are for instance the pentaerythritol esters of long chain fatty acids, such as oleic, stearic and lauric acids, and the alkyl and aryl phosphites.
  • the alkyl phenate and the sequestering agent may each useful-1y be employed to the extent of 5% by Weight of the chlorinated paraflinic hydrocarbon, although for most applications 0.l1% by weight will be found to give adequate protection against metal staining. Greater amounts than 5% by weight may be employed but such amounts give no technical advantage and in general they are not economic.
  • chlorinated paraflinic hydrocarbons containing 826 carbon atoms per molecule and at least 25 by weight of chlorine may be employed in the stabilised lubricating oil additives of the invention.
  • chlorinated paraflinic hydrocarbons containing 826 carbon atoms per molecule and at least 25 by weight of chlorine may be employed in the stabilised lubricating oil additives of the invention.
  • chlorrne containing 40-70% by weight of chlorrne.
  • chlorinated hydrocarbons stabilised according to the present invention may additionally contain conventional heat stabilisers, for example epoxidised oils.
  • a mixture of C C paraflins chlorinated to a chlorine content of 65% by weight and containing 1% by weight of epoxidised oil as heat stabiliser is stabilised according to the present invention by addition thereto of 0.25% of barium octyl phenol sulphide and 0.25% of pentaerythritol dioleate, the percentages being calculated on the weight of chlorinated paraffins.
  • the stabilised chlorinated parafl'ln when added in amount of 40% by weight to a mineral cutting oil provides a heavy duty cutting lubricant which gives no noticeable staining of ferrous meta-1 parts.
  • a stabilized lubricating oil additive which consists essentially of at least one liquid chlorinated parafiinic hydrocarbon containing 8-26 carbon atoms per molecule and about 25 to 70% by Weight of chlorine, 0.l5% of a metal alkyl phenate wherein said metal is selected from the group consisting of barium, calcium and magnesium, and 0.15% of an oil-soluble sequestering agent for heavy metals, the percentages of said phenate and said sequestering agent being calculated on the weight of said chlorinated paraffinic hydrocarbon.
  • a stabilized lubricating oil additive which consists essentially of at least one liquid chlorinated paraflinic hydrocarbon containing 826 carbon atoms per molecule and 4070% by weight of chlorine, 0.11% of barium octyl phenol sulphide and (ll-1% of pentaerythritol di oleate, the percentages being calculated on the Weight of chlorinated parafiinic hydrocarbon.
  • a lubricating oil composition consisting essentially of a rnajor amount of a mineral cutting oil and a stabilizing amount of a stabilized lubricating oil additive which consists essentially of at least one liquid chlorinated paraffinic hydrocarbon containing 826 carbon atoms per molecule and 40-70% by weight of chlorine, 0.1-1% of barium octyl phenol sulphide and 0.14% of pentaerythritol dioleate, the percentages being calculated on the weight of chlorinated paraffinic hydrocarbon.

Description

United States Patent 3,210,277 STABILISATION OF CHLORINATED HYDROCARBONS George Edward 'Swift, Buncorn, England, assignor to Imperial Chemical Industries Limited, London, England, a corporation of Great Britain No Drawing. Filed Aug. '10, 1964, Ser. No. 388,720 Claims priority, application Great Britain, Aug. 26, 1963, 33,698 63 Claims. (Cl. 252-417) The present invention relates to the stabilisation of chlorinated hydrocarbons. More particularly it relates to the stabilisation of liquid chlorinated long chain paraffinic hydrocarbons for use as oil additives.
It is known to improve the properties of mineral oil lubricants when working under heavy loads by incorporating therein a proportion of relatively involatile liquid chlorinated paraflinic hyrocarbon, for instance a paraflinic hydrocarbon containing at least eight carbon atoms per molecule and chlorinated to a chlorine content of at least 25% by weight, particularly 4070% by weight. Although the extreme pressure lubricant properties of mineral oils are considerably improved by such additions, the improved lubricants are found to have the disadvantage of staining metal surfaces with which they come into contact in use, as for instance in metal cutting and drawing operations and in lubricated gear assemblies.
We have now found that the aforementioned disadvantage can be avoided by incorporating in chlorinated parafiins that are to be employed as oil additives a stabiliser system comprising a barium, calcium or magnesium alkyl phenate and a sequestering agent.
According to the present invention a stabilised lubricating oil additive comprises at least one liquid chlorinated parafiinic hydrocarbon containing 826 carbon atoms per molecule and at least 25% by weight of chlorine, 0.1-5 of a barium, calcium or magnesium alkyl phenate as hereinafter defined and 0.15% of an oil-soluble sequestering agent for heavy metals, the percentages of the said phenate and the said sequestering agent being calculated on the weight of chlorinated paraflinic hydrocarbon.
The barium, calcium and magnesium phenates employed in the present invention have in their simplest form the structure:
Where M is an atom of barium, calcium or magnesium, R is hydrogen or an alkyl group containing 1-10 carbon atoms, and R is an alkyl group containing 1-10 carbon atoms. When R as Well as R is an alkyl group R will usually be the same as R since such compounds are the more easily prepared. The phenate employed may, however, contain additionally a proportion of sulphur in the form of a single sulphur linkage or a dithio linkage between the two aromatic nuclei. The formulae of such phenates may be represented by the following two structures I and II, such compounds being alternatively known as alkyl phenol sulphides and disulphides:
3,210,277 Patented Get. 5, 1965 O l I R1 R1 Eta %112 where M, R and R are as defined in the preceding paragraph.
Suitable sequestering agents are for instance the pentaerythritol esters of long chain fatty acids, such as oleic, stearic and lauric acids, and the alkyl and aryl phosphites.
The alkyl phenate and the sequestering agent may each useful-1y be employed to the extent of 5% by Weight of the chlorinated paraflinic hydrocarbon, although for most applications 0.l1% by weight will be found to give adequate protection against metal staining. Greater amounts than 5% by weight may be employed but such amounts give no technical advantage and in general they are not economic.
As stated hereinbet'ore, chlorinated paraflinic hydrocarbons containing 826 carbon atoms per molecule and at least 25 by weight of chlorine may be employed in the stabilised lubricating oil additives of the invention. Of this range of compounds we prefer to employ for most applications those containing 40-70% by weight of chlorrne.
It is already known to add stabilisers to chlorinated hydrocarbons of the aforesaid range for the purpose of inhibiting decomposition by heat. It must be understood that chlorinated hydrocarbons stabilised according to the present invention may additionally contain conventional heat stabilisers, for example epoxidised oils.
We have found that if 0.15% by weight of a barium, calcium or magnesium alkyl phenate is added to the chlorinated hydrocarbon without an accompanying sequestering agent the staining of metal surfaces is prevented but that the heat stability of the chlorinated hydrocarbon (as determined by the standard test of measuring hydrogen chloride evolution on blowing nitrogen through the material heated for 4 hours at C.) is thereby reduced, even when conventional heat stabilisers such as epoxidised oils are present. We have found, however, that addition of an oil-soluble sequestering agent for heavy metals prevents this deleterious eifect, possibly by inactivating barium, calcium and magnesium chlorides which are thought to be formed in traces in the respective mixtures and to have a catalytic effect on decomposition of the chlorinated hydrocarbon.
The invention is illustrated by the following example but is not limited thereby. A mixture of C C paraflins chlorinated to a chlorine content of 65% by weight and containing 1% by weight of epoxidised oil as heat stabiliser is stabilised according to the present invention by addition thereto of 0.25% of barium octyl phenol sulphide and 0.25% of pentaerythritol dioleate, the percentages being calculated on the weight of chlorinated paraffins. The stabilised chlorinated parafl'ln, when added in amount of 40% by weight to a mineral cutting oil provides a heavy duty cutting lubricant which gives no noticeable staining of ferrous meta-1 parts.
What we claim is:
1. A stabilized lubricating oil additive which consists essentially of at least one liquid chlorinated parafiinic hydrocarbon containing 8-26 carbon atoms per molecule and about 25 to 70% by Weight of chlorine, 0.l5% of a metal alkyl phenate wherein said metal is selected from the group consisting of barium, calcium and magnesium, and 0.15% of an oil-soluble sequestering agent for heavy metals, the percentages of said phenate and said sequestering agent being calculated on the weight of said chlorinated paraffinic hydrocarbon.
Z. A stabilized lubricating oil additive as claimed in claim 1 wherein said oil soluble heavy metal sequestering agent is selected from the group consisting of pentaerythritol esters of long chain fatty acids, alkyl phosphites and aryl phosphites.
3. A stabilized lubricating oil additive which consists essentially of at least one liquid chlorinated paraflinic hydrocarbon containing 826 carbon atoms per molecule and 4070% by weight of chlorine, 0.11% of barium octyl phenol sulphide and (ll-1% of pentaerythritol di oleate, the percentages being calculated on the Weight of chlorinated parafiinic hydrocarbon.
4. A lubricating oil composition consisting essentially of a rnajor amount of a mineral cutting oil and a stabilizing amount of a stabilized lubricating oil additive which consists essentially of at least one liquid chlorinated paraffinic hydrocarbon containing 826 carbon atoms per molecule and 40-70% by weight of chlorine, 0.1-1% of barium octyl phenol sulphide and 0.14% of pentaerythritol dioleate, the percentages being calculated on the weight of chlorinated paraffinic hydrocarbon.
5. The lubricating oil as claimed in claim 4 wherein the stabilized lubricating oil additive comprises about 40% by Weight of said lubricating oil.
6. A stabilised lubricating oil additive according to claim 1 wherein the said sequestering agent is a pentaerythritol ester of a long chain fatty acid.
7. A stabilised lubricating oil additive according to claim 1 wherein the said sequestering agent is a phosphite selected from the group consisting of alkyl phosphites and aryl phosphites.
S. A stabilised lubricating oil additive as claimed in claim 10 wherein the chlorinated paraffinic hydrocarbon component contains 40-70% by Weight of chlorine.
9. A stabilised lubricating oil additive as claimed in claim 10 wherein the phenate is present to the extent of 0.14% by weight of the chlorinated paraflinic hydrocarbon.
ltl. A stabilised lubricating oil additive as claimed in claim 10 wherein the sequestering agent is present to the extent of 0.11% by weight of the chlorinated paraffinic hydrocarbons.
References Cited by the Examiner UNITED STATES PATENTS 2,362,289 11/44 Mikeska 25242.7
FOREIGN PATENTS 487,630 10/52 Canada. 749,3 54 5/56 Great Britain.
DANIEL E. WYMAN, Primary Examiner.

Claims (1)

1. A STABILIZED LUBRICATING OIL ADDITIVE WHICH CONSISTS ESSENTIALLY OF AT LEAST ONE LIQUID CHLORINATED PARAFFINIC HYDROCARBON CONTAINING 8-26 CARBON ATOMS PER MOLECULE AND ABOUT 25 TO 70% BY WEIGHT OF CHLORINE, 0.1-5% OF A METAL ALKYL PHENATE WHEREIN SAID METAL IS SELECTED FROM THE GROUP CONSISTING OF BARIUM, CALCIUM AND MAGNESIUM, AND 0.1-5% OF AN OIL-SOLUBLE SEQUESTERING AGENT FOR HEAVY METALS, THE PERCENTAGES OF SAID PHENATE AND SAID SEQUESTERING AGENT BEING CALCULATED ON THE WEIGHT OF SAID CHLORINATED PARAFFINIC HYDROCARBON.
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3367867A (en) * 1966-01-04 1968-02-06 Chevron Res Low-foaming overbased phenates
US4119548A (en) * 1977-10-28 1978-10-10 Mobil Oil Corporation Reaction product of nickel thiobis(alkylphenolate) and thiobis(alkylphenol) and organic compositions containing the same
US4198303A (en) * 1978-05-01 1980-04-15 Mobil Oil Corporation Antioxidant lubricant compositions
US4211663A (en) * 1978-05-01 1980-07-08 Mobil Oil Corporation Alkali metal containing transition metal complexes of thiobis (alkylphenols) as stabilizers for various organic media
US4226733A (en) * 1978-11-17 1980-10-07 Mobil Oil Corporation Lubricant compositions stabilized against ultra-violet degradation
US4295888A (en) * 1976-01-19 1981-10-20 Imperial Chemical Industries Limited Solvent compositions

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US2362289A (en) * 1938-12-16 1944-11-07 Standard Oil Dev Co Lubricating compositions
CA487630A (en) * 1952-10-28 Marion Church James Stabilized chlorinated paraffins
GB749354A (en) * 1954-06-11 1956-05-23 Shell Refining & Marketing Co Lubricating oil compositions

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NL171020B (en) * 1948-12-29 Union Carbide Corp METHOD FOR SEPARATING ACID GASES FROM A STEAM CONTAINING GAS MIXTURE.
FR1072289A (en) * 1953-03-09 1954-09-10 Standard Oil Dev Co Lubricating oil additive
GB778818A (en) * 1955-02-15 1957-07-10 Exxon Research Engineering Co Improved lubricating compositions
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CA487630A (en) * 1952-10-28 Marion Church James Stabilized chlorinated paraffins
US2362289A (en) * 1938-12-16 1944-11-07 Standard Oil Dev Co Lubricating compositions
GB749354A (en) * 1954-06-11 1956-05-23 Shell Refining & Marketing Co Lubricating oil compositions

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3367867A (en) * 1966-01-04 1968-02-06 Chevron Res Low-foaming overbased phenates
US4295888A (en) * 1976-01-19 1981-10-20 Imperial Chemical Industries Limited Solvent compositions
US4119548A (en) * 1977-10-28 1978-10-10 Mobil Oil Corporation Reaction product of nickel thiobis(alkylphenolate) and thiobis(alkylphenol) and organic compositions containing the same
US4198303A (en) * 1978-05-01 1980-04-15 Mobil Oil Corporation Antioxidant lubricant compositions
US4211663A (en) * 1978-05-01 1980-07-08 Mobil Oil Corporation Alkali metal containing transition metal complexes of thiobis (alkylphenols) as stabilizers for various organic media
US4226733A (en) * 1978-11-17 1980-10-07 Mobil Oil Corporation Lubricant compositions stabilized against ultra-violet degradation

Also Published As

Publication number Publication date
DE1270722C2 (en) 1975-12-18
NL6409320A (en) 1965-03-01
ES303397A1 (en) 1965-03-16
DE1270722B (en) 1968-06-20
GB1019924A (en) 1966-02-09

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