Composition, method and use

Abstract

A quaternary ammonium compound of formula (I): (I) wherein R.sup.0, R.sup.1, R.sup.2 and R.sup.3 is each independently an optionally substituted hydrocarbyl group, X is a linking group, R.sup.4 is an optionally substituted alkylene group, R5 is hydrogen or an optionally substituted alkyl, alkenyl or aryl group, and n is 0 or a positive integer, provided that n is not 0 when R5 is hydrogen. ##STR00001##

Claims

1. A quaternary ammonium compound of formula (I): ##STR00020## wherein R.sup.0, R.sup.1, R.sup.2 and R.sup.3 is each independently an optionally substituted hydrocarbyl group, X is a linking group, R.sup.4 is an optionally substituted alkylene group, R.sup.5 is hydrogen or an optionally substituted alkyl, alkenyl or aryl group, and n is 0 or a positive integer, provided that n is not 0 when R.sup.5 is hydrogen.

2. A method of preparing a quaternary ammonium salt, the method comprising reacting (a) a tertiary amine of formula R.sup.1R.sup.2R.sup.3N with (b) an acid-derived alkylating agent in the presence of (c) a compound of formula HOOCXCOO—(R.sup.4O).sub.n—R.sup.5, wherein R.sup.4 is an optionally substituted alkylene group, R.sup.5 is hydrogen or an optionally substituted alkyl, alkenyl or aryl group, and n is 0 or a positive integer, provided that n is not 0 when R.sup.5 is hydrogen.

3. The method according to claim 2 wherein component (b) is an epoxide.

4. A composition comprising a quaternary ammonium compound of formula (I): ##STR00021## wherein R.sup.0, R.sup.1, R.sup.2 and R.sup.3 is each independently an optionally substituted hydrocarbyl group, X is a linking group, R.sup.4 is an optionally substituted alkylene group, R.sup.5 is hydrogen or an optionally substituted alkyl, alkenyl or aryl group, and n is 0 or a positive integer, provided that n is not 0 when R.sup.5 is hydrogen.

5. The composition according to claim 4 wherein the composition is an additive composition for a fuel or lubricating oil.

6. The composition according to claim 4 wherein the composition is a fuel composition.

7. A method of improving the performance of an engine, the method comprising combusting in the engine a fuel composition comprising as an additive a quaternary ammonium compound of formula (I): ##STR00022## wherein R.sup.0, R.sup.1, R.sup.2 and R.sup.3 is each independently an optionally substituted hydrocarbyl group, X is a linking group, R.sup.4 is an optionally substituted alkylene group, R.sup.5 is hydrogen or an optionally substituted alkyl, alkenyl or aryl group, and n is 0 or a positive integer, provided that n is not 0 when R.sup.5 is hydrogen.

8. The salt according to claim 1 wherein HOOCXCOO—(R.sup.4O).sub.n—R.sup.5 is derived from a hydrocarbyl substituted succinic acid or a hydrocarbyl substituted succinic anhydride.

9. The salt according to claim 1 wherein each R.sup.4 is ethylene or propylene.

10. The salt according to claim 1 wherein R.sup.5 is hydrogen and n is at least 1.

11. The salt according to claim 1 wherein R.sup.5 is an optionally substituted alkyl group having 4 to 40 carbon atoms and n is from 0 to 40.

12. The salt according to claim 1 wherein each of R.sup.1 and R.sup.2 is independently an optionally substituted alkyl group having from 1 to 12 carbon atoms.

13. The salt according to claim 1 wherein R.sup.3 is an alkyl or hydroxyalkyl group having 1 to 10 carbon atoms.

14. The salt according to claim 1 wherein R.sup.3 is selected from the group consisting of: (1) a polyisobutenyl group having a molecular weight of from 100 to 5000; (2) an optionally substituted alkylene phenol moiety of formula (A) or (B) ##STR00023## wherein n is 0 to 4, R is an optionally substituted hydrocarbyl group, R′ is an optionally substituted alkyl, alkenyl or aryl group; and L is a linking group; and (3) a succinimide moiety of formula: ##STR00024## wherein R is an optionally substituted hydrocarbyl group and L is a linking group.

15. The salt according to claim 1 wherein R.sup.0 as is a group of formula: ##STR00025## wherein each of R.sup.9, R.sup.10, R.sup.11, R.sup.12 is independently hydrogen or an optionally substituted alkyl, alkenyl or aryl group.

16. The salt according to claim 1 wherein X is an optionally substituted alkylene or arylene group.

17. The salt according to claim 1 wherein the quaternary ammonium compound is the reaction product of: (a) a tertiary amine of formula R.sup.1R.sup.2R.sup.3N wherein each of, R.sup.1, R.sup.2 and R.sup.3 is independently an optionally substituted alkyl group having 1 to 12 carbon atoms; (b) an epoxide selected from the group consisting of: styrene oxide, ethylene oxide, propylene oxide, butylene oxide, epoxyhexane, octene oxide, stilbene oxide, 2-ethylhexyl glycidyl ether, 1,2-epoxydodecane and other alkyl and alkenyl epoxides having 2 to 50 carbon atoms; and (c) a compound of formula HOOCXCOO—(R.sup.4O).sub.n—R.sup.5 wherein X is CH.sub.2CHR or CHRCH.sub.2 wherein R is an optionally substituted hydrocarbyl group; and n is more than 1, R.sup.4 is an ethylene or propylene group and R.sup.5 is hydrogen; or n is 0 or and R.sup.5 is a C1 to C20 alkyl group.

18. The salt according to claim 1 wherein the quaternary ammonium compound is the reaction product of: (a) a tertiary amine of formula R.sup.1R.sup.2R.sup.3N wherein each of, R.sup.1, R.sup.2 and R.sup.3 is independently an alkyl or hydroxyalkyl group having 1 to 6 carbon atoms; (b) an epoxide selected from the group consisting of: propylene oxide, butylene oxide and 2-ethylhexyl glycidyl ether; and (c) a compound of formula HOOCXCOO—(R.sup.4O).sub.n—R.sup.5 which is the reaction product of a succinic acid or anhydride having a C.sub.20 to C.sub.24 alkyl or alkenyl substituent and an alcohol selected from the group consisting of: polypropylene glycol having a number average molecular weight of 300 to 800, 2-ethylhexanol and butanol.

19. The composition according to claim 4 wherein the composition is a lubricating composition.

20. The composition according to claim 4 wherein the composition is a gasoline fuel composition.

21. The composition according to claim 20 wherein the gasoline fuel composition comprises one or more further additives selected from the group consisting of: a) carrier oils; b) acylated nitrogen compounds which are the reaction product of a carboxylic acid-derived acylating agent and an amine; c) hydrocarbyl-substituted amines wherein the hydrocarbyl substituent is substantially aliphatic and contains at least 8 carbon atoms; d) mannich base additives comprising nitrogen-containing condensates of a phenol, aldehyde and primary or secondary amine; e) aromatic esters of a polyalkylphenoxyalkanol; and f) additional quaternary ammonium salts.

22. The composition according to claim 20 wherein the gasoline fuel composition comprises a mixture of two or more quarternary ammonium salt additives.

23. The method as defined in claim 7 wherein the additive is used as a detergent to combat deposits in a gasoline fuel composition in a spark ignition engine.

24. The method according to claim 7 wherein the engine is a direct injection spark ignition engine.

25. The method according to claim 7 which achieves “keep clean” performance.

26. The method according to claim 7 which achieves “clean up” performance.

27. The method according to claim 7 wherein the deposits are injector deposits.

28. The method according to claim 27 wherein the deposits are internal injector deposits.

29. The method according to claim 7 which combats intake valve deposits.

30. The method according to claim 7 which achieves an improvement in performance of one or more of: improved fuel economy; reduced maintenance; less frequent overhaul or replacement of injectors; improved driveability; improved power; or improved acceleration.

Description

EXAMPLE 1

(1) Additive A1, a quaternary ammonium salt additive of the invention was prepared as follows:

(2) (a) A mixture of alkenes having 20 to 24 carbon atoms was heated with 1.2 molar equivalents of maleic anhydride. On completion of the reaction excess maleic anhydride was removed by distillation. The anhydride value of the substituted succinic anhydride product was measured as 2.591 mmolg.sup.−1.

(3) This product was then heated with one molar equivalent of polypropylene glycol having a number average molecular weight of 425, and the reaction was monitored by FTIR to provide the half ester/half acid product.

(4) (b) 1 molar equivalent of diethyl ethanolamine was reacted with 1.5 molar equivalents of butylene oxide and 6 molar equivalents of water at 60° C. in toluene for 10 hours in the presence of the half ester/half acid provided in the step (a) to form a quaternary ammonium compound. Volatiles were removed in vacuo.

(5) Compounds A2 to A21 detailed in table 1 were prepared by an analogous method.

(6) TABLE-US-00001 TABLE 1 Compound R H-(OR.sup.4)n-OR.sup.5 Amine Epoxide A1 C20-24 polypropylene Diethyl ethanolamine Butylene oxide glycol Mn425 A2 C20-24 polypropylene Dimethyl ethanolamine Butylene oxide glycol Mn425 A3 C20-24 polypropylene Triethylamine Butylene oxide glycol Mn425 A4 C20-24 polypropylene Tributylamine Butylene oxide glycol Mn425 A5 C20-24 tripropylene glycol Dimethyl ethanolamine Butylene oxide A6 C20-24 tripropylene glycol Diethyl ethanolamine Butylene oxide A7 C20-24 tripropylene glycol Triethylamine Butylene oxide A8 C20-24 tripropylene glycol Tributylamine Butylene oxide A9 C20-24 triethyleneglycol Dimethyl ethanolamine Butylene oxide A10 C20-24 triethyleneglycol Diethyl ethanolamine Butylene oxide A11 C20-24 triethyleneglycol Triethylamine Butylene oxide A12 C20-24 triethyleneglycol Tributylamine Butylene oxide A13 C20-24 polypropylene Dimethyl ethanolamine Butylene oxide glycol Mn725 A14 C20-24 polypropylene Diethyl ethanolamine Butylene oxide glycol Mn725 A15 C20-24 polypropylene Triethylamine Butylene oxide glycol Mn725 A16 C20-24 polypropylene Tributylamine Butylene oxide glycol Mn725 A17 C20-24 Tetraethyleneglycol Dimethyl ethanolamine Butylene oxide A18 C20-24 Tetraethyleneglycol Diethyl ethanolamine Butylene oxide A19 C20-24 tetraethyleneglycol Triethylamine Butylene oxide A20 C20-24 tetraethyleneglycol Tributylamine Butylene oxide A21 C20-24 polyethyleneglycol Dimethyl ethanolamine Butylene oxide Mn400 A22 C20-24 2-Ethylhexanol N,N-diethyl ethanolamine Butylene oxide A23 C20-24 Butanol N,N-diethyl ethanolamine Butylene oxide A24 C20-24 Poly(ethylene glycol) 2-[2-(Dimethylamino)ethoxy] 1,2- Mn400 ethanol epoxydodecane A25 C20-24 Poly(ethylene glycol) N,N-dimethyl Benzylamine 2-Ethylhexyl Mn400 Glycidyl Ether A26 C20-24 Poly(ethylene glycol) N,N-dimethyl ethanolamine 1,2- Mn400 epoxydodecane A27 C20-24 Poly(ethylene glycol) N,N-dimethyl ethanolamine Styrene Oxide Mn400 A28 C20-24 Poly(ethylene glycol) N,N-Dimethyl 2-Ethylhexyl Mn400 octadecylamine Glycidyl Ether A29 C20-24 Poly(ethylene glycol) N,N-Dimethyl Butylene oxide Mn400 octadecylamine A30 C20-24 Poly(ethylene glycol) N,N-Dimethyl 1,2- Mn400 octadecylamine epoxydodecane A31 C20-24 Poly(ethylene glycol) N,N-Dimethyl Styrene Oxide Mn400 octadecylamine A32 C20-24 Poly(propylene glycol) N,N-dimethyl 2-Ethylhexyl Mn425 Benzylamine Glycidyl Ether A33 C20-24 Poly(propylene glycol) N,N-dimethyl Butylene oxide Mn425 Benzylamine A34 C20-24 Poly(propylene glycol) N,N-dimethyl Styrene Oxide Mn425 Benzylamine A35 C20-24 Poly(propylene glycol) N,N-dimethyl 1,2- Mn425 Benzylamine epoxydodecane A36 C20-24 Poly(propylene glycol) N,N-Dimethyl 2-Ethylhexyl Mn425 octadecylamine Glycidyl Ether A37 C20-24 Poly(propylene glycol) N,N-Dimethyl Butylene oxide Mn425 octadecylamine A38 C20-24 Poly(propylene glycol) N,N-Dimethyl Styrene Oxide Mn425 octadecylamine A39 C20-24 Tetradecanol N,N-diethyl ethanolamine Butylene oxide A40 C20-24 Tri(propylene glycol) 2-[2-(Dimethylamino)ethoxy] 2-Ethylhexyl ethanol Glycidyl Ether A41 C20-24 Tri(propylene glycol) 2-[2-(Dimethylamino)ethoxy] 1,2- ethanol epoxydodecane A42 C20-24 Tri(propylene glycol) 2-[2-(Dimethylamino)ethoxy] Styrene Oxide ethanol A43 C20-24 Tri(propylene glycol) N,N-dimethyl Benzylamine 2-Ethylhexyl Glycidyl Ether A44 C20-24 Tri(propylene glycol) N,N-dimethyl Benzylamine Butylene oxide A45 C20-24 Tri(propylene glycol) N,N-dimethyl Benzylamine 1,2- epoxydodecane A46 C20-24 Tri(propylene glycol) N,N-dimethyl Benzylamine Styrene Oxide A47 C20-24 Tri(propylene glycol) N,N-dimethyl ethanolamine 1,2- epoxydodecane A48 C20-24 Tri(propylene glycol) N,N-Dimethyl 2-Ethylhexyl octadecylamine Glycidyl Ether A49 C20-24 Tri(propylene glycol) N,N-Dimethyl Butylene oxide octadecylamine A50 C20-24 Tri(propylene glycol) N,N-Dimethyl 1,2- octadecylamine epoxydodecane A51 C20-24 Tri(propylene glycol) N,N-Dimethyl Styrene Oxide octadecylamine A52 1000PI Tri(propylene glycol) N,N-dimethyl ethanolamine 1,2- B epoxydodecane