Patent GB-797452-A (GB)
Title: Improved lubricating oil compositions
Inventor: HUGHES JOHN
IPC: C10M133/16
Filed: 1956-01-18
Abstract: Aromatic acid salts of partially acylated aliphatic di- or polyamines for addition to lubricating oils (see Group III) are prepared by direct neutralization of the amidoamines with the acids in a solvent, e.g. petroleum or by double decomposition of the hydrochlorides or sulphates of the amidoamines with alkali metal salts of the acids in a solvent.  Salt-forming aromatic acids mentioned are carboxylic acids, e.g. butyl and octyl benzoic acids, naphthoic acids, and octadecyl, di-isopropyl and mixed C8-18 alkylated salicylic acids; sulphonic acids, e.g. benzene and alkyl (e.g. nonyl and dodecyl) benzene sulphonic acids, di-isopropyl naphthalene sulphonic acid, butyl phenol sulphonic acids and sulphonic acids derived from aromatic fractions from petroleum and their alkylated products; and phenols, e.g. octyl and dodecyl phenols, butyl and amyl naphthols, and the condensation products of formaldehyde or acetaldehyde with alkylated phenols such as p-octyl phenol.  Typical di- and polyamines include 1,2-diaminoethane, 1,2- and 1,3-diaminopropane, 1,2-, 1,3- and 1,4-diaminobutane, 2,3-diaminohexane, 1,8-diamino-octane, diethylene triamine, triethylene tetramine, tetraethylene pentamine, dipropylene triamine, tripropylene tetramine, N-butyl ethylene diamine and di-(2-aminoethyl) sulphide.  These may be partially acylated with any carboxylic acid, e.g. benzoic, salicylic, octyl salicylic, naphthoic, resin, tall oil, caproic, lauric, stearic or palmitic acid or the naphthenic acids from petroleum.  The partial amides may be prepared by mixing equimolecular parts of the amine and the acid, or a halide, nitrile or ester thereof, and heating in an autoclave at 170-200 DEG  C. for 5 to 8 hours.  In examples preparative details are given for: (i) the salt obtained by double decomposition between sodium C14-18 alkyl salicylate and the hydrochloride of N-(2-aminoethyl) naphthenamide obtained by partially acylating ethylene diamine with naphthenic acids; (ii) the salt obtained by double decomposition between sodium "Kerex" sulphonate and the hydrochloride of (i) ("Kerex" is a Registered Trade Mark for an aromatic extract derived from kerosine); and (iii) the salt obtained by neutralization with C14-18 alkyl salicylic acids of ethylene diamine partially acylated with tall oil acid.  Other salts which may be prepared by similar means are the di-isopropyl salicylate, benzene sulphonate and dodecyl benzene sulphonate of ethylene diamine partially acylated with naphthenic acid and the "Kerex" sulphonates of 1,2- or 1,3-diaminopropane, 1,8-diamino-octane or diethylene triamine partially acylated with naphthenic acid. Specification 783,882 is referred to.ALSO:A lubricating oil composition comprises a major proportion of a lubricating oil and a minor proportion of an oil-soluble salt of an aromatic acid and a partially acylated di- or polyamine.  The lubricating oil may be natural or synthetic, e.g. paraffinic, naphthenic or asphaltic mineral oils or synthetic oils such as polymerized olefines, esters, e.g. di(2-ethylhexyl) sebacate, dioctyl phthalate and trioctyl phosphate and silicone polymers or any blend of such oils with one another or with fatty oils such as castor oil or lard oil. Salt-forming aromatic acids mentioned are carboxylic acids, e.g. butyl and octyl benzoic acids, naphthoic acids, octadecyl and di-isopropyl salicylic acids and mixtures of C8-C18 alkylated salicylic acids; sulphonic acids, e.g. benzene and alkyl (e.g. nonyl and dodecyl) benzene sulphonic acids, di-isopropyl naphthalene sulphonic acid, butyl phenol sulphonic acids and sulphonic acids from aromatic fractions from petroleums and their alkylated products; and phenols, e.g. octyl and dodecyl phenols, butyl and amyl naphthols and the condensation products of formaldehyde or acetaldehyde with alkylated phenols such as p-octyl phenol.  Typical di- and poly-amines include 1,2-diaminoethane, 1,2- and 1,3-diamino propane, 1,2-, 1,3- and 1,4-diamino butane, 2,3-diaminohexane, 1,8-diamino-octane, diethylene triamine, triethylene tetramine, tetraethylene pentamine, dipropylene triamine, tripropylene tetramine, N-butyl ethylene diamino and di-(2-aminoethyl) sulphide. These may be partially acylated with any carboxylic acid, e.g. benzoic, salicylic, octyl salicylic, naphthoic, rosin, tall oil, caproic, lauric, stearic, or palmitic acids especially naphthenic acids from petroleum refining.  The preparation of such compounds is described and exemplified (see Group IV (b)).  Optional ingredients mentioned include detergents, e.g. alkaline earth metal salts of C14-18 alkylated salicylic acids and of organic sulphonic acids such as petroleum sulphonic acids; V.I. improvers, e.g. "Acryloids," polymerized isobutylene and alkyl styrenes; pour point depressants, e.g. wax-naphthalene condensation products; corrosion inhibitors, e.g. nitrites, such as sodium, lithium, di-isopropyl ammonium, and dicyclohexyl ammonium nitrites; E.P. agents, e.g. S-and P-containing compounds such as P2S5-terpene reaction products, calcium or zinc dicyclohexyl or methylcyclohexyl thiophosphates; and anti-foam agents, e.g. organic silicone polymers such as dimethyl silicone.  In the examples there are mentioned the salts of N-(2-aminoethyl) naphthenamide with a mixture of C14-18 alkylated salicylic acids and with "Kerex" (Registered Trade Mark) sulphonic acid; the salt of ethylene diamine partially acylated with tall oil acid and a mixture of C14-18 alkylated salicylic acids; the di-isopropyl salicylic acid, benzene sulphonic acid, and dodecyl benzene sulphonic acid salts of ethylene diamine partially acylated with naphthenic acid; and the "Kerex" sulphonic acid salts of the mono-amides of 1,2-diamino propane, 1,3 - diaminopropane, 1,8 - diamino octane and diethylene triamine and naphthenic acid. These salts are tested in admixture with mineral lubricity oils. Specification 783,882, [Group IV (b)], is referred to.