Patent GB-1199422-A (GB)
Title: Nitrogen-Containing Detergent Materials and Compositions containing the same
IPC: C10M135/08
Filed: 1967-11-24
Abstract: 1,199,422. Olefin polymer derivative. MONSANTO CO. 24 Nov., 1967 [25 Nov., 1966], No. 53703/67. Heading C3P. [Also in Divisions C4-C5] Compounds of formula where R and R<SP>1</SP> are each hydrogen, hydrocarbyl or substituted hydrocarbyl, at least one of which has at least 40 carbon atoms and having together at least 50 carbon atoms; R<SP>2</SP> and R<SP>3</SP> are hydrogen, hydrocarbyl or substituted hydrocarbyl having 1 to 30 carbon atoms; provided that when any of R, R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> are substituted the weight of the substituents deos not exceed 15% of the total weight of the groups; R<SP>4</SP> is hydrogen, optionally substituted C 1-10  hydrocarbyl or an optionally substituted heterocyclic group having 4 to 10 carbon atoms and 1 to 4 oxygen, nitrogen and/or sulphur atoms; may be prepared by reacting an olefin polymer of formula R-CR<SP>2</SP>=CR<SP>3</SP>-R<SP>1</SP> with a sulphur trioxide yielding material and a nitrile of formula R<SP>4</SP>CN. The products may be hydrolysed and optionally halogenated to give compounds of formula where R 5  is hydrogen or CO-R<SP>4</SP> and X is halogen or OM where M is hydrogen or a metal or ammonium cation; and the compounds and hydrolysis products may be further reacted with amines and optionally with an oxide, halide, acid or acid ester of boron or with a zinc or nickel salt to give further products, all of which compounds and products may be used as detergent additives in lubricating oils. Preferred polymers are of propylene and butene, but many others including copolymers of olefins with butadiene, isoprene, piperylene, chloroprene, 1,3-hexadiene, styrene and substituted styrenes are specified. The sulphur trioxide yielding substance may be sulphur trioxide, sulphuric acid, chlorosulphonic acid or a complex of sulphur trioxide with pyridine, dioxane, thioxane or an alkyl phosphate. Many other reactants are listed and examples describe the reaction of acetonitrile and sulphur trioxide with (1, 3 and 4) polybutene, (2) polypropene and (5) polyisobutene; the hydrolysis of (5) with sodium hydroxide to give sodium 2- ethylidene amino-1-polyisobutenyl sulphonate, and of 4-polybutenyl-4,6-dimethyl-2-dioxo-1,2, 5-oxathiazine with ammonium hydroxide to give ammonium 2-ethylidene amino-1-polybutenyl sulphonate and with sodium hydroxide and subsequently hydrochloric acid to give 2- acetamido-1-polybutenyl sulphonic acid; the reaction of (5) with zinc acetate, nickel acetate, calcium oxide or excess calcium oxide and carbon dioxide; and the reaction of 4-polybutenyl - 4,6 - dimethyl - 2 - dioxo - 1,2,5 - oxathiazine with (14) N,N-dimethylaminopropylamine, (15) 1- (2-aminoethyl)-2-propylimidazoline, (16 and 28-31) diethylene triamine, (17) ethylenediamine, (18) tetraethylene pentamine, (19) pentaethylene hexamine, (20) thiourea, (21) urea, (22) diethanolamine, (23) 1-(5-amino- 3-azapentyl) succinimide, (24) 1-(5-amino-3- azapentyl) maleimide, (25) 1-(5-amino-3-azapentyl)-3-polybutenyl succinimide, and (26) 1- (2 - aminoethyl) - 2 - methyl imidazoline, and the further reaction of products (29) with boric acid, (30) with zinc sulphate and (31) with zinc acetate.