Patent GB-1121641-A (GB)
Title: Additives for lubricating compositions
Inventor: ELLIOTT JOHN SCOTCHFORD
IPC: C10M135/10
Filed: 1965-01-08
Abstract: Oil soluble compounds suitable as lubricant additives and of formula R1-X-A-Bn where R1 is an alkyl or alkenyl group having at least 12 carbon atoms, X is an ester, amide or imide grouping, A is an organic radical containing at least one basic nitrogen atom, n is 1 to 6 and B is -(CRR)mSO3H and is attached through the carbon atom to a nitrogen atom of A, where each R is hydrogen, alkyl, substituted alkyl, phenyl, substituted phenyl or any two substituents R on adjoining carbon atoms are taken together to form a cyclic system and m is 3 or 4, or a salt thereof, may be prepared by reacting the corresponding alkyl or alkenyl ester, amide or imide with an amine and a sultone or with a prereaction product of the amine and sultone. R1 is preferably derived from a polyolefin, e.g. polyisobutylene of molecular weight 700-3000, hydrogenated if desired.  Preferred compounds may be prepared by reacting polyisobutenyl succinic anhydrides with polyamines, optionally modifying the intermediate with a carboxylic acid, aldehyde or ketone, and further reacting the intermediate or modified intermediate with a sultone.  Many suitable starting materials are described, and in examples propane sultone is reacted with intermediates prepared from polyisobutenyl succinic anhydride and (I and XXX) tetraethylene pentamine, (IV) reaction product of pentaethylene hexamine and dicyandiamide, (V and XXXII) commercial isomeric pentaethylene hexamines and hexamines containing piperazine rings, (VI and XXXI) pentaethylene hexamine, (VII, XXVIII and XXXVII) triethylene tetramine, (VIII) diethylene triamine, (IX) ethylene diamine, (X and XI) polyethylene imines, (XII) mixed polyethylene polyamines, (XIII and XXXIII) N - b  - aminoethyl piperazine, (XIV) dimethylaminopropylenediamine, (XV) N-2-aminoethyl morpholine, (XVI) p - phenylene diamine, (XVII) N-2-aminoethyl ethanolamine, (XVIII) hydroxytetraethylene tetramine, (XIX) reaction product of g -butyrolactone and tetraethylene pentamine, (XX) guanidine carbonate, and tetrathylene pentamine together with (XXI) acetic acid, (XXII) lauric acid, (XXIII) oleic acid, (XXIV) adipic acid, (XXV) salicylaldehyde, (XXVI) benzaldehyde and (XXVII) formic acid; polyisobutenyl succinic anhydride is reacted with (XXXIV) tetraethylene pentamine and 1,1,3 - trimethylp opane sultone, (XXXV) tetraethylene pentamino sulphonic acid and (XXXVI) a mixed polyaminosulphonic acids; and a polyisobutenyl monocarboxylic acid is reacted with a polyalkylene polyamine and propane sultone.  The product of (I) is further reacted with (II and III) barium hydroxide and (XXXIX) calcium oxide and carbon dioxide.ALSO:Lubricating compositions comprise a major proportion of a lubricating oil and a minor proportion of a detergent and dispersant additive of formula R1-X-A-Bn, where R1 is an alkyl or alkenyl group having at least 12 carbon atoms, X is an ester, amide or imide grouping, A is an organic radical containing at least one basic nitrogen atom, n is 1 to 6 and B is -(CRR)mSO3H and is attached through the carbon atom to a nitrogen atom of A, where each R is hydrogen, alkyl, substituted alkyl, phenyl, substituted phenyl or any two substituents R on adjacent carbon atoms are taken together to form a cyclic system and m is 3 or 4, or a salt thereof.  Preferred additives are formed by reacting polyisobutenyl succinic anhydrides with polyamines, optionally with an acid, aldehyde or ketone, and finally with a sultone; or by reacting the polyisobutenyl succinic anhydrides with polyamine/sultone reaction products. The compositions may also comprise conventional copper deactivators, pour-point depressants, antioxidants and viscosity index improvers.  Examples describe compositions comprising mineral lubricating oil and additives of the invention prepared by reacting propane sultone with intermediates from polyisobutenyl succinic anhydride and tetraethylene pentamine alone and with acetic, lauric, oleic, adipic or formic acid, salicylaldehyde or benzaldehyde, reaction product of pentaethylene hexamine and dicyandiamide, isomeric commercial pentaethylene hexamines and hexamines containing piperazine rings, pentaethylene hexamine, triethylene tetramine, diethylene triamine, ethylene diamine, polyethylene polyimines, mixed polyethylene polyamines, N-b -aminoethyl piperazine, dimethylaminoethyl propylenediamine, N - 2 - aminoethyl morpholine, p - phenylene-diamine, N - 2 - aminoethyl ethanolamine, hydroxytetraethylene tetramine, reaction product of g -butyrolactone and tetraethylene pentamine and guanidine carbonate; by reacting polyisobutenyl succinic anhydrides with tetraethylene pentamine and 1,1,3 - trimethylpropane sulphone, tetraethylene pentamino sulphonic acid and mixed polyaminosulphonic acids; and by reacting a polyisobutenyl monocarboxylic acid with a polyalkylene polyamine and propane sultone; the first above additive being optionally reacted with barium hydroxide or calcium oxide and carbon dioxide.  Other ingredients of the compositions are a methacrylate polymer V.I. improver, a barium salt of phosphosulphurized polyisobutylene neutralized in the presence of an alkylphenol and treated with carbon dioxide, zinc dialkyl dithiophosphates derived from isopropanol and methyl isobutyl carbinol or from isopropanol and 1-methylheptyl alcohol, and a hindered phenol antioxidant.ALSO:Amino alkane sulphonic acids are prepared by reacting amines with sultones. In examples (XXXV) tetraethylene pentamino propane sulphonic acid is prepared by reacting tetraethylene pentamine with propane sultone and (XXXVI) a polyamine trimethylpropane sulphonic acid is prepared by reacting a commercial mixture said to comprise isomeric pentaethylene hexamines and related hexamines containing piperazine rings with 1,1,3-trimethylpropane sultone.