Patent GB-863339-A (GB)
Title: Lubricating oil compositions
IPC: C10M169/00
Filed: 1958-12-01
Abstract: A lubricating oil additive (see Group III) is an oil-soluble aliphatic compound having as substituents at least one oxygen-containing group Y and 1-4 groups-S.(CH2)n.X, wherein Y is an alcohol (-OH), ether (-o-), carboxylic acid (-COOH) or ester (-COOC-) group, n is an integer from 1 to 4, X is -OR or -COOR and R is hydrogen or a C1-C4 alkyl group, at least one of the -S.(CH2)n X groups being separated from a Y group by a chain of at least 7 carbon atoms. The compound may be prepared by reacting a mercapto compound of formula HS(CH2)nX (e.g. a mercapto aliphatic carboxylic acid or ester thereof, or a mercapto-alkanol or ether thereof) with an ethylenically unsaturated aliphatic compound containing at least one oxygen-containing group Y and having an ethylenically unsaturated bond separated from an oxygencontaining group Y by a chain of at least 7 carbon atoms (e.g. an unsaturated fatty acid, an unsaturated fatty alcohol, or an unsaturated ester derived from an unsaturated fatty acid or unsaturated alcohol or both).  Examples of suitable compounds are (1) a mixture of 9-and 10-carboxymethyl-mercaptostearic acid prepared by reacting oleic acid and mercapto acetic acid, (2) a mixture of ethyl 9- and 10-carboxymethyl-mercapto-stearate prepared by reacting ethyl oleate and mercapto-acetic acid, (3) a mixture of 9- and 10-carboxymethylmercapto-12-hydroxystearic acid prepared by reacting ricinoleic acid and mercapto-acetic acid, (4) a mixture of glyceryl tris (9- and 10-carboxymethyl-mercaptostearate (prepared by reacting glyceryltrioleate and mercapto-acetic acid, (5) a mixture of 9- and 10-carboxymethylmercaptostearyl alcohol prepared by reacting oleyl alcohol and mercapto-acetic acid, (6) a mixture of 9- and 10-carboxymethylmercaptostearyl 91- and 101- carboxymethylmercaptostearate prepared by reacting oleyl oleate and mercapto-acetic acid, (7) a mixture of O-(9- and 10-[21-hydroxyethylmercapto]-stearoyl) -611-oxa-11-thia-caproic acid prepared by reacting vinyl oleate and mercapto-acetic acid and then reacting the product with mercapto-ethanol, (8) a mixture of 12- and 13-(21 hydroxyethylmercapto) - 3 - thialheneicosanoic acid prepared by reacting 1,9-octadecadiene and 2-mercapto-acetic acid and then reacting the product with 2-mercaptoethanol, (9) a mixture of 5-hydroxy-3-thia-amyl 91- and 101-carboxymethylmercaptostearate prepared by reacting equimolecular proportions of oleic acid, 2, 21-thiodiethanol and mercapto-acetic acid and (10) a mixture of 9- and 10-carboxymethylmercaptostearyl-(21-hydroxyethylmercaptoun decanoate prepared by reacting equimolecular proportions of oleyl 10- undecenoate, 2-mercapto-acetic acid and 2-mercaptoethanol. Specification 651,712 is referred to.ALSO:A lubricating composition, suitable for use at extreme pressures, comprises a major proportion of a lubricating oil and a minor proportion of an oil-soluble aliphatic compound having as substituents at least one oxygen-containing group Y and 1 - 4 groups -S.(CH2)nX, wherein Y is an alcohol (-OH), ether (-O-), carboxylic acid (-COOH) or ester (-COOC-) group, n is an integer from 1 to 4, X is -OR or -COOR and R is hydrogen or a C1-C4 alkyl group, at least one of the -S.(CH2)n.X groups being separated from a Y group by a chain of at least 7 carbon atoms.  The compound may be prepared by reacting a mercapto compound of formula HS(CH2)nX (e.g. a mercapto aliphatic carboxylic acid or ester thereof, or a mercaptoalkanol or ether thereof) with an ethylenically unsaturated aliphatic compound containing at least one oxygen-containing group Y and having an ethylenically unsaturated bond separated from an oxygen-containing group Y by a chain of at least 7 carbon atoms (e.g. an unsaturated fatty acid, an unsaturated fatty alcohol, or an unsaturated ester derived from an unsaturated fatty acid or unsaturated alcohol or both).  Examples of suitable compounds are (1) a mixture of 9- and 10-carboxymethyl - mercaptostearic acid prepared by reacting oleic acid and mercapto-acetic acid, (2) a mixture of ethyl 9- and 10-carboxymethylmercaptostearate prepared by reacting ethyl oleate and mercapto-acetic acid, (3) a mixture of 9- and 10-carboxymethylmercapto-12-hydroxystearic acid prepared by reacting ricinoleic acid and mercapto-acetic acid, (4) a mixture of glyceryl tris (9- and 10-carboxymethylmercaptostearate) prepared by reacting glyceryl trioleate and mercapto-acetic acid, (5) a mixture of 9- and 10-carboxymethylmercaptostearyl alcohol prepared by reacting oleyl alcohol and mercaptoacetic acid, (6) a mixture of 9- and 10-carboxymethylmercaptostearyl 91- and 101-carboxymethylmercaptostearate prepared by reacting oleyl oleate and mercapto-acetic acid, (7) a mixture of O-(9-and 10-[21-hydroxethylmercapto]-stearoyl) -611-oxa-311-thia-caproic acid prepared by reacting vinyl oleate and mercapto-acetic acid and then reacting the product with mercaptoethanol, (8) a mixture of 12- and 13-(21-hydroxyethylmercapto) - 3 - thiaheneicosanoic acid p  prepared by reacting 1,9-octadecadiene and 2-mercapto-acetic acid and then reacting the product with 2-mercapto-ethanol, (9) a mixture of 5-hydroxy-3-thia-amyl 91- and 101-carboxymethylmercaptostearate prepared by reacting equimolecular proportions of oleic acid, 2,21-thiodiethanol and mercapto-acetic acid and (10) a mixture of 9- and 10-carboxymethylmercaptostearyl - (21 - hydroxyethyl - mercapto)-undecanoate prepared by reacting equimolecular proportions of oleyl 10-undecenoate, 2-mercapto-acetic acid and 2-mercaptoethanol.  Where the compound forms an opaque solution in the lubricating oil, a clear solution may be obtained by the addition of a clarifier which may be a branched-chain alkanol, a fatty acid having at least 10 carbon atoms or a partial ester of such fatty acid with a polyhydric alcohol (e.g. glycerol, pentaerythritol, triethylene glycol, propylene glycol, sorbitol or mannitol).  The lubricating oil may be a mineral and/or a synthetic oil and may be blended with fatty oils.  Synthetic lubricating oils mentioned are polymerized olefins, alkylated aromatics, isomerized waxes, polyglycols or ethers thereof and esters of aliphatic dibasic acids (e.g. di-2-ethylhexyl sebacate or adipate).  The lubricating composition may also contain silicone anti-foaming agents, alkyl phenol antioxidants, and polyacrylate ester viscosity index improvers.  Sixteen examples of suitable lubricating compositions are given.  For comparison purposes, mineral oil compositions are described which contain C16 alkenyl succinic acid, malonic acid, 3-hexadecyladipic acid, thiodiglycollic acid, thioalpha, alpha1 - bis - (stearic acid), dodecyl - mercapto - succinic acid, heptyl - mercapto - succinic acid, alpha-mercapto-benzoic acid, glycerol mono-oleate, lauric acid, C13 oxo alcohol, 3-(21-ethylhexyl) adipic acid or a mixture of 9- and 10-carboxystearic acid.  Specification 651,712 is referred to.