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United States Patent Office Patented July 7, 1970

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United States Patent Office Patented July 7, 1970 3,519,564 United States Patent Office Patented July 7, 1970 2 often used to improve extreme pressure properties of 3,519,564 lubricants, especially gear oils and the like, but these sul HETEROCYCLIC NITROGEN-SULFUR COMPOS fur compounds have a strong tendency to cause corro TIONS AND LUBRICANTS CONTAINING THEM sion of metal parts, especially bearings which may con Paul W. Vogel, Lyndhurst, Ohio, assignor to The Lubris zol Corporation, Wicklife, Ohio, a corporation of tain copper, silver or other sulfur-reactive metals. When Ohio contacted with ferrous metal surfaces, many of these No Drawing. Continuation-in-part of application Ser. No. additives contribute to the formation of rust thereon. 663,208, Aug. 25, 1967. This application May 17, 1968, Therefore, it is frequently necessary to add a corrosion Ser. No. 731,363 inhibiting or rust-inhibiting additive to the lubricant to Int, C, C10m 1/38 O counteract this tendency of other additives. U.S. C. 252-47.5 10 Claims A principal object of the present invention, therefore, is to prepare new compositions of matter suitable for use as lubricant additives. ABSTRACT OF THE DISCLOSURE A further object is to prepare lubricant additives which Hydrazine (or substituted hydrazines) and carbon di 5 protect metal surfaces from rust and corrosion, especially sulfide react with acylated polyamines (wherein the acylat when caused by sulfur-containing additives. ing agent is a carboxylic compound, preferably a succinic Other objects will in part be obvious and will in part compound, containing at least about 20 carbon atoms) appear hereinafter. to produce compositions useful as corrosion and rust in Component A in the compositions of this invention is hibitors for lubricants. The compositions contain hetero 20 hydrazine or a substituted hydrazine. The corresponding cyclic compounds of the formula hydrazine hydrate may also be used. For reasons of economy and particular suitability, unsubstituted hydra N-N zine (NH4) is preferred; but hydrazines substituted Y- C-SENER9.9 (either symmetrically or unsymmetrically) with one or N / 25 more hydrocarbon radicals are also suitable. As used S herein, the term "hydrocarbon radical” refers to alkyl, wherein Y is -SH or cycloalkyl, aryl, alkaryl and aralkyl radicals. It also in 6 e cludes Substantially hydrocarbon radicals; that is, radicals -SENR and NR containing non-hydrocarbon substituents which do not is the acylated polyamine residue. 30 detract Substantially from the hydrocarbon character of the radical. Examples of such substituents are ether, ester, nitro and halogen groups. Examples of substituted hydrazines are methylhydra This application is a continuation-in-part of copending zine, N,N-dimethylhydrazine, N,N'-dimethylhydrazine, application Ser. No. 663,208, filed Aug. 25, 1967, now 35 phenylhydrazine, N-phenyl-N'-ethylhydrazine, N-(p-tolyl)- abandoned. N'-(n-butyl) hydrazine, N-(p-nitrophenyl)-N-methylhy This invention relates to new compositions of matter drazine, N,N'-di-(p-chlorophenyl) hydrazine and N-phen useful as lubricant additives, particularly for corrosion yl-N'-cyclohexylhydrazine. and rust inhibition. More particularly, the invention re Component B is carbon disulfide. It may be used in lates to novel compositions of matter prepared by react 40 the free state or in the form of carbon disulfide-producing ing (A) a compound of the formula compounds such as metal trithiocarbonates, dithiocarba mates or Xanthates. R2 Component C is an acylated alkylene polyamine or 45 hydroxyalkyl-substituted alkylene polyamine of the type R3 disclosed in U.S. Pats. 3,219,666 and 3,272,746. The dis closures of these two patents are hereby incorporated by wherein R, R2 and R3 are hydrogen or hydrocarbon radi reference in the present application. cals, at least one of R, R2 and R3 being hydrogen; The polyamines used for the preparation of component (B) carbon disulfide; and (C) an acylated nitrogen C include, in general, alkylene amines containing about containing composition characterized by the presence 50 10 or less alkylene groups joined through nitrogen atoms. within its structure of (1) at least one acyl, acyloxy or They include principally the ethylene amines, propylene acylimidoyl radical containing at least about 20 carbon amines, butylene amines and homologs thereof, and also atoms, and (2) a nitrogen-containing radical in which a piperazines and aminoalkyl-substituted piperazines. Hy nitrogen atom is attached directly to said radical (1), said droxyalkyl-substituted alkylene polyamines are also con nitrogen-containing radical being derived from an alkyl 55 templated for use in preparing component C. Typical ene polyamine or a hydroxyalkyl-substituted alkylene examples of Suitable amines are ethylene diamine, tri polyamine. ethylene tetramine, pentaethylene hexamine, propylene diamine, tripropylene tetramine, di-(trimethylene) tri Modern lubricants, including engine oils, gear lubri amine, 1,4-bis-(2-aminoethyl)piperazine, 1-(2-aminopro cants, automatic transmission fluids and the like, owe 60 pyl)piperazine, N-(2-hydroxyethyl)ethylene diamine, their efficiency in large part to the presence therein of 1-(2-hydroxyethyl)piperazine, and 2-heptadecyl-1-(2-hy numerous additives which improve various properties of droxyethyl)-imidazoline. Mixtures of these amines may the lubricant. Many of these additives, however, cause also be used. new problems of their own when they are added to the The preferred amines are the polyethylene polyamines lubricant. For example, sulfur-containing compounds are 65 containing from two to about eight amino groups per 3,519,564 3 4. molecule. A commercially available mixture of polyethyl thereof. This latter reaction is preferred, especially where ene polyamines containing an average of about 3-7 amino the acid-producing compound is maleic acid or anhydride. groups per molecule is particularly suitable. The resulting product is a hydrocarbon-substituted suc The acylating agent used for preparing component C cinic acid or derivative thereof. The reaction leading to is a carboxylic acid-producing compound containing at its formation involves merely heating the two reactants at least about 20 and preferably at least about 50 carbon about 100-200 C. The substituted succinic acid or anhy atoms. By "carboxylic acid-producing compound' is dride thus obtained, may, if desired, be converted to the meant an acid, anhydride, acid halide, ester, amide, imide, corresponding acid halide by reaction with known halo amidine or the like; the acids and anhydrides are pre genating agents such as phosphorus trichloride, phos ferred. phorus pentachloride or thionyl chloride. The acylating agent is usually prepared by the reaction IO For the formation of component C, the hydrocarbon (more fully described hereinafter) of a relatively low substituted succinic anhydride or acid, or other acylating molecular weight carboxylic acid-producing compound agent, and the alkylene polyamine are heated to a tem with a hydrocarbon source containing at least about 20 perature above about 80° C., preferably about 100-250 carbon atoms. The hydrocarbon source should be sub 5 C. The process may in Some instances be carried out at stantially saturated, i.e., at least about 95% of the total a temperature below 80° C. to produce a product having number of carbon-to-carbon covalent linkages should be predominantly salt linkages. When the reaction is effected saturated. It should also be substantially free from pend above 80 C., the product has predominantly amide, ant groups containing more than about six aliphatic car imide or amidine linkages. The use of a solvent such as bon atoms. It may be a substantially hydrocarbon source, 20 mineral oil, benzene, toluene, naphtha or the like is often as defined hereinabove. desirable to facilitate control of the reaction temperature. The preferred hydrocarbon sources are those derived The relative proportions of the acylating agent and from substantially saturated petroleum fractions and ole the alkylene polyamine are such that at least about one fin polymers, particularly polymers of monoolefins having half the stoichiometrically equivalent amount of the poly from 2 to about 30 carbon atoms. Thus, the hydrocarbon 25 amide is used for each equivalent of acylating agent. source may be derived from a polymer of ethylene, pro In this regard it will be noted that the equivalent weight pene, 1-butene, isobutene, 1-octene, 3-cyclohexyl-1-butene, of the alkylene polyamine is based upon the number of 2-butene, 3-pentene or the like. Also useful are interpoly amine radicals therein, and the equivalent weight of the mers of olefins such as those illustrated above with other acylating agent is based on the number of acidic or po polymerizable olefinic substances such as styrene, chloro 30 tentially acidic radicals. (Thus, the equivalent weight of prene, isoprene, p-methylstyrene, piperylene and the like. a hydrocarbon-substituted succinic acid or anhydride is In general, these interpolymers should contain at least one-half its molecular weight.) Although a minimum of about 80%, preferably at least about 95%, on a weight one-half equivalent of polyamine per equivalent of acylat basis of units derived from the aliphatic monoolefins. ing agent should be used, there does not appear to be Another suitable hydrocarbon source comprises satu 35 an upper limit for the amount of polyamine. If an ex rated aliphatic hydrocarbons such as highly refined high cess is used, it merely remains in the product unreacted molecular weight white oils or synthetic alkanes. without any apparent adverse effects. Ordinarily, about In many instances, the hydrocarbon source should con 1-2 equivalents of polyamine are used per equivalent of tain an activating polar radical to facilitate its reaction acylating agent. with the low molecular weight acid-producing compound. 40 In an alternative method for producing component The preferred activating radicals are halogen atoms, espe C, the alkylene polyamine is first reacted with a low cially chlorine, but other suitable radicals include sulfide, molecular weight, unsaturated carboxylic acid-producing disulfide, nitro, mercaptain, ketone and aldehyde groups.
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