US3372119A - Lubricant compositions containing polychloroalkyl benzene extreme pressure additives - Google Patents

Lubricant compositions containing polychloroalkyl benzene extreme pressure additives Download PDF

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US3372119A
US3372119A US438368A US43836865A US3372119A US 3372119 A US3372119 A US 3372119A US 438368 A US438368 A US 438368A US 43836865 A US43836865 A US 43836865A US 3372119 A US3372119 A US 3372119A
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chlorinated
benzene
chlorine
weight
additives
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Demoures Bernard
Schneider Gerard
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups 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
    • 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
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    • 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
    • C10M2207/046—Hydroxy ethers
    • 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
    • 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
    • C10M2207/12—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
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic 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
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic 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
    • C10M2207/283—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
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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
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • 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
    • 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
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26—Amines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/30—Heterocyclic compounds
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • 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
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    • 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
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    • C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
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    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/08—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds
    • C10M2227/083—Sn compounds
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings
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    • 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

  • a lubricant additive for use at extreme pressures comprising a mixture of a chlorinated alkyl benzene having a chlorine content of from 50 to 75% by weight, at least 75 of which is bound to the alkyl carbon atoms, and a resinous polychlorobenzene polysulfide soluble in hydrocarbon oils and containing from 15 to 25% sulfur and from 44 to 55% chlorine.
  • the present invention relates to new additives for lubricants and in particular to products capable of imparting extreme pressure properties to lubricating oils, making them more suitable for use as cutting oils. It is also concerned with a process for the preparation of these new products.
  • chlorinated derivatives sulphur or phosphorus derivatives
  • chlorinated diphenyls or polyphenyls there may be mentioned the chlorinated diphenyls or polyphenyls and particularly the chlorinated paraflins.
  • chloralkyl benzenes as for example the 30.5% chlorinated dodecylbenzene, obtained in the form of a reddish brown opaque oil by chlorination of the hydrocarbon in the presence of ultraviolet rays at increasing temperatures which vary between 100 and 220 C.
  • the new additives according to the invention have an efiiciency which is distinctly better than that of the already known chlorinated derivatives, that is to say, the rates of wear of the metal element working under high pressures are comparatively much lower and, in addition, the seizing phenomena of the element or tool only occur at very strong pressures which are higher than those corresponding for example, to the chlorinated paraflins.
  • these additives can be used in very small quantities and, in any case, for identical rates of wear and seizing pressures, certainly smaller than those of the prior known chloralkyl benzenes.
  • additives according to the present invention are formed by aromatic hydrocarbons substituted by one or more chlorinated alkyl radicals, at least one of these radicals containing a minimum of 5 carbon atoms, the total chlorine content in the said hydrocarbons being greater than 50%
  • the long-chain alkyl radical may comprise 5 to 30 carbon atoms, it being possible for the aliphatic chain to be linear or branched.
  • the precentages of chlorine fixed onthe aliphatic radical may vary between wide limits and the additives according to the invention may contain in total 50 to of chlorine.
  • the chlorination process according to the invention consists in introducing a current of chlorine into the hydrocarbon or mixture of aromatic alkyl hydrocarbons kept in the dark at a temperature between 40 and 180 C.
  • the reaction which is prefer-ably effected in the absence of a solvent, does not generally require the use of a catalyst. Nevertheless, according to a modification of the process according to the invention, it is possible to employ small quantities, for example, 2 to 8% by weight of the batch, of a catalyst which promotes the chlorination of the aralkyl hydrocarbon on the side chain or chains.
  • This catalyst may be formed, for example, by a phosphorus polyhalide, such as phosphorus trichloride. Under these conditions, the reaction temperature can be lowered appreciably and it is then generally between 40 and C.
  • aralkyl hydrocarbons As initial aralkyl hydrocarbons, it is for example possible to use benzene hydrocarbons substituted by a longchain alkyl radical, such as: pentyl, hexyl, octyl, nonyl, decyl, dodecyl, tridecyl, tetradecyl, etc.
  • the alkyl radical may in addition be branched, it being possible for one or several hydrogens of the carbon atoms in the linear chain to be substituted by alkyl radicals, such as: methyl, ethyl, propyl, etc.
  • branched alkyl radicals 2-methyl pentyl, 2,3-dimethyl pentyl, 2-methyl-4-propyl pentyl, 2-ethyl hexyl, 4,6-dimethyl nonyl, etc.
  • Additives which are likewise advantageous are formed by chlorination products of alkylates or mixtures of heavy alkylates, obtained at the time of distillation of alkylation products of benzene with branched or unbranched olefins (as for example the tetramer of propylene).
  • alkyl or polyalkyl benzenes known under the registered trademarks: Progiline 152, Solgil 54, Solgil 109, Solgil 110, Alkylat 1163, etc.
  • Progiline 152 the alkyl or polyalkyl benzenes known under the registered trademarks: Progiline 152, Solgil 54, Solgil 109, Solgil 110, Alkylat 1163, etc.
  • the reaction generally takes place under atmospheric pressure but obviously it is possible to work under higher or lower pressures. It may be conducted continuously or intermittently and it is possible to determine the proportion of fixed chlorine by the usual methods, as for example the measurement of the variations in physical characteristics, such as density, refractive index, etc.
  • the chlorinated products obtained according to the invention are in the form of more or less viscous liquids or solids, which are generally colorless or with a slight yellowish orange coloration.
  • the total proportion of chlorine therein is preferably between 52 and 60% for the purposes according to the invention.
  • the mixed additive in accordance with the modification of the invention may contain variable proportions of each of its constituents, for example, to 90 parts by weight of polychloralkyl aryl compound to, respectively, 90 to 10 parts of resinous haloaryl polysulphide.
  • the content of this mixed additive in the lubricants may advantageously be from 2 to 10% by weight.
  • chlorinated additives according to the invention are relatively stable over a period of time at normal temperature, others are decomposed more or less quickly from 30 to 40 0, thereby liberating hydrochloric acid. It is possible considerably to limit this degradation by the chlorinated product having incorporated therein one or more heat stabilizers and/ or light stabilizers of known types.
  • the additives may have added thereto: metal salts of fatty acids, such as barium or cadmium laurates and stearates, organo-tin derivatives, epoxidized agents, hydroxybenzophenones, derivatives of alkylene oxide, sulphonamides, morpholines, etc.
  • epoxidized compounds such as epoxidized soya oil
  • a hydroxybenzophenone such as 2-hydroxy-4-methoxybenzophenone
  • corrosion inhibitors of known type, as for example amines or polyamines, mercaptans, alkali compounds, capable of neutralizing the decomposition products which could be formed with the use of the cutting oil.
  • the quantity of chlorinated additive to be incorporated into a lubricant for permitting it to be used as a cutting oil at extreme pressure is obviously a function of the nature of this lubricant and of the work for which it is intended to be used. This quantity may vary generally between fairly wide limits, for example between 0.2 and 20% of the weight of lubricant. In the case of cutting oils for high pressure, the desirable quantities are frequently between 2 and 10% by weight. It is generally advantageous to use a proportion of additive such that the chlorine content in the lubricating composition is of the order of 1.5 to 4%. It is then found that there is a very great increase in the binding limit and also a considerable reduction in the wear of the tool.
  • the lubricating oils containing the additives according to the invention may be used for numerous purposes, as for example hypoid drives, motors, cutting of metals, lubrication of drilling bits and rod sections when sinking petroleum wells, etc.
  • Examples 1 to 6 illustrate the preparation of a certain number of aralkyl hydrocarbons chlorinated to more than 50% in accordance with the invention.
  • Examples 7 to 14 illustrate the good results obtained when using these chlorinated products as extreme-pressure additives, and also their superiority as compared with previously known chlorinated additives.
  • Example 1 Employed as initial hydrocarbon is a cut of alkylation products of benzene, boiling between 160 and 210 C. and containing a mixture of alkyl benzenes of the mean empirical formula C H C H 410 g. of the aforementioned hydrocarbon are introduced into a two-litre spherical flask kept in the dark and equipped with a stirrer device, a condenser, a gas supply tube and a heating system. Then, after having heated the flask to about C., a stream of chlorine is caused to bubble therein at an average rate of 24 l./hr.
  • Example 4 The same initial materials as in Example 3 were used, but with the following proportions and under the following conditions:
  • Example 5 The operation was carried out as indicated in Example 1, using as starting material an alkyl benzene fraction boiling between 160 and 240 C., in which the number of carbon atoms of the alkyl chains varied between 5 and 11.
  • an alkyl benzene fraction boiling between 160 and 240 C. in which the number of carbon atoms of the alkyl chains varied between 5 and 11.
  • Example 7 For the purpose of studying its extreme-pressure characteristics in a lubricant, the product obtained in Example 1 was diluted, on the one hand, in a naphthene type oil known as SHELL carnea 21 (trademark) and, on the other hand, in a paraffin type oil known as 350 Neutral (trademark), which designates a lubricating grease obtained by distillation of petroleum, and of which the Saybolt viscosity at 37.8 C. is 350; the dilution rate was such that the chlorine content in each of the oils was 2.64% (i.e. about 4.7 g. of adjuvant in 100 g. of mixture).
  • a naphthene type oil known as SHELL carnea 21 (trademark)
  • 350 Neutral trademark
  • the dilution rate was such that the chlorine content in each of the oils was 2.64% (i.e. about 4.7 g. of adjuvant in 100 g. of mixture).
  • the 30% chlorinated hydrocarbon was used in a proportion clearly higher than that of the 55 chlorinated product, so as to have, after the same rates of dilution in the oil, equal contents of chlorine (2.50%).
  • Example 12 The present example is given to serve as comparison with the modification of the invention illustrated by Example 13. It concerns a resinous polychlorobenzene polysulphide containing 19% of sulfur and 49% of chlorine, which belongs to the group of additives -for lubricating greases described in French Patent No. 1,339,529.
  • This polysulphide was prepared in the following way: 20 g. of AlCl were added to 817 g. of a mixture comprising 30% of trichloro-1,2,3-benzene, 65% of trichloro- 1,2,4-benzene and 5% of tetrachloro-1,2,4,5- and -1,2,3,4- benzenes; 405 g. of S Cl previously diluted with 363 g. of the same trichlorobenzenes and tetrachlorobenzenes as indicated above, are progressively introduced over a period of 2 hours into the well stirred mixture, brought to 45% C.
  • the total mixture then was kept at 45 C., while stirring, for half an hour, after which it was heater to 80 C. for 2 hours.
  • the product of the reaction was then poured into water; the elimination of the AlCl was obtained by washing with dilute HCl, followed by a washing with a dilute solution of sodium carbonate, then Washing operations with water until neutral.
  • the organic phase after decantation of the aqueous phase, was subjected to a distillation at mm. Hg until its temperature had reached 195 to 200 C.
  • 260 g. of trichlorobenzenes were eliminated and there were recovered 950 g. of resinous polychlorobenzene polysulphides containing 49% by weight of Cl and 19% by weight of S.
  • Example 14 Tests similar to those of Example 13 were carried out with a /75 composite additive, that is to say, a mixture of 25 parts by weight of the same polychlorobenzene polysulphide with 75 parts of the same polychloroalkyl benzene as in the preceding example.
  • a /75 composite additive that is to say, a mixture of 25 parts by weight of the same polychlorobenzene polysulphide with 75 parts of the same polychloroalkyl benzene as in the preceding example.
  • the chlorinated alkyl benzenes used in the examples were stabilized beforehand, as indicated in the foregoing description.
  • the thermal stability at 140 C., in the presence of iron and copper, was very good after one Week.
  • the resistance to water was excellent and in addition no trace of corrosion was observed with metals such as steels, copper and cast iron.
  • the results of the examples which have been described show that the additives according to the invention have practically the same activity in the naphthene oils and the parafiin oils. These results are always better than those which are obtained when other chlorinated additives of known type are used.
  • a lubricant composition containing, as a principal lubricating constituent, a lubricating oil and from 0.2 to 20% by weight of the composition of an extreme pressure lubricant additive comprising a mixture of from 10 to 90 parts by weight of a chlorinated alkyl benzene having a chlorine content of fro-m 50 to by weight, at least 75% of the chlorine content of said additive being bound to alkyl carbon atoms and at least one of the chloroalkyl radicals of the said additive having from 5 to 30 carbon atoms, and from 90 to 10 parts by weight of a resinous polychlorobenzene polysulfide soluble in hydrocarbon oils and containing from 15 to 25% sulfur and 44 to 55% chlorine.
  • an extreme pressure lubricant additive comprising a mixture of from 10 to 90 parts by weight of a chlorinated alkyl benzene having a chlorine content of fro-m 50 to by weight, at least 75% of the chlorine content of said additive being bound to alkyl carbon atoms and
  • lubricant composition as defined in claim 1 in which the lubricating oil is a naphthenic base oil or a paraffinic base oil.

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2121824A (en) * 1938-06-28 Lubricants
US2208161A (en) * 1939-10-19 1940-07-16 Lubri Zol Dev Corp Lubricating composition
FR1335514A (fr) * 1961-12-30 1963-08-23 Progil Sulfures d'halogéno-aryles
US3175972A (en) * 1965-03-30 Lubricant composition and method
US3179592A (en) * 1963-03-20 1965-04-20 Diamond Alkali Co Lubricant containing bis (trichloromethyl) benzene

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2121824A (en) * 1938-06-28 Lubricants
US3175972A (en) * 1965-03-30 Lubricant composition and method
US2208161A (en) * 1939-10-19 1940-07-16 Lubri Zol Dev Corp Lubricating composition
FR1335514A (fr) * 1961-12-30 1963-08-23 Progil Sulfures d'halogéno-aryles
US3179592A (en) * 1963-03-20 1965-04-20 Diamond Alkali Co Lubricant containing bis (trichloromethyl) benzene

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FR1410218A (fr) 1965-09-10

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