阅读说明：本技术 组合物和与其有关的方法及用途 (Compositions and methods and uses relating thereto ) 是由 M.佩茨 K.莱曼凯斯 A.N.罗斯 于 2018-03-28 设计创作，主要内容包括：式(I)的季铵化合物：其中R<Sup>0</Sup>、R<Sup>1</Sup>、R<Sup>2</Sup>和R<Sup>3</Sup>各自独立地是任选地被取代的烃基,X是连接基团,R<Sup>4</Sup>是任选地被取代的亚烷基,R<Sup>5</Sup>是氢或任选地被取代的烷基、烯基或芳基基团,且n是0或正整数,前提条件是,当R<Sup>5</Sup>是氢时,n不是0。<Image he="105" wi="379" file="100004_DEST_PATH_IMAGE002.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(A quaternary ammonium compound of formula (I): wherein R is 0 、R 1 、R 2 And R 3 Each independently is an optionally substituted hydrocarbyl group, X is a linking group, R 4 Is optionally substituted alkylene, R 5 Is hydrogen or an optionally substituted alkyl, alkenyl or aryl group and n is 0 or a positive integer, with the proviso that when R is 5 When it is hydrogen, n is not 0.)

1. A quaternary ammonium compound of formula (I):

Wherein R is⁰、R¹、R²And R³Each independently is an optionally substituted hydrocarbyl group, X is a linking group, R⁴Is optionally substituted alkylene, R⁵Is hydrogen or an optionally substituted alkyl, alkenyl or aryl group and n is 0 or a positive integer, with the proviso that when R is⁵When it is hydrogen, n is not 0.

2. A process for preparing a quaternary ammonium salt which comprises reacting a compound of formula (c) HOOCXCOO- (R)⁴O)_n-R⁵In the presence of a compound of (a) R¹R²R³Reacting a tertiary amine of N with (b) an acid-derived alkylating agent, wherein R⁴Is optionally substituted alkylene, R⁵Is hydrogen or an optionally substituted alkyl, alkenyl or aryl group and n is 0 or a positive integer, with the proviso that when R is⁵When it is hydrogen, n is not 0.

3. The method of claim 2, wherein component (b) is an epoxide.

4. a composition comprising a quaternary ammonium compound of formula (I):

Wherein R is⁰、R¹、R²and R³Each independently is an optionally substituted hydrocarbyl group, X is a linking group, R⁴Is optionalA substituted alkylene group, R⁵Is hydrogen or an optionally substituted alkyl, alkenyl or aryl group and n is 0 or a positive integer, with the proviso that when R is⁵When it is hydrogen, n is not 0.

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

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

7. Use of a quaternary ammonium compound of formula (I) as an additive in a fuel or lubricant composition:

Wherein R is⁰、R¹、R²And R³Each independently being an optionally substituted alkyl, alkenyl or aryl group, X being a linking group, R⁴Is optionally substituted alkylene, R⁵Is hydrogen or an optionally substituted alkyl, alkenyl or aryl group and n is 0 or a positive integer, with the proviso that when R is⁵when it is hydrogen, n is not 0.

8. A method of improving engine performance, the method comprising combusting in an engine a fuel composition comprising as an additive a quaternary ammonium compound of formula (I):

Wherein R is⁰、R¹、R²And R³Each independently is an optionally substituted hydrocarbyl group, X is a linking group, R⁴Is optionally substituted alkylene, R⁵Is hydrogen or an optionally substituted alkyl, alkenyl or aryl group, and n is 0 or a positive integer,Provided that when R is⁵When it is hydrogen, n is not 0.

9. A salt, composition, method or use according to any preceding claim wherein hooxcoo- (R)⁴O)_n-R⁵Derived from hydrocarbyl-substituted succinic acid or hydrocarbyl-substituted succinic anhydride.

10. A salt, composition, method or use according to any preceding claim wherein each R is⁴Is ethylene or propylene, preferably-CH₂CH₂-or-CH (CH)₃)CH₂-, more preferably-CH (CH)₃)CH₂-。

11. A salt, composition, method or use according to any preceding claim wherein R⁵Is hydrogen and n is at least 1.

12. The salt, composition, method or use according to any one of claims 1-10, wherein R⁵Is an optionally substituted alkyl group having 4 to 40 carbon atoms and n is 0 to 40.

13. A salt, composition, method or use according to any preceding claim wherein R¹And R²Each of which is independently an optionally substituted alkyl group having 1-12 carbon atoms.

14. A salt, composition, method or use according to any preceding claim wherein R³Is an alkyl or hydroxyalkyl group having 1 to 10 carbon atoms.

15. The salt, composition, method or use according to any one of claims 1-13, wherein R³Selected from:

(1) Polyisobutenyl groups having a molecular weight of 100-;

(2) An optionally substituted alkylene phenol group of formula (A) or (B)

Wherein n is 0-4, preferably 1, R^xIs an optionally substituted hydrocarbon radical, R^yIs an optionally substituted alkyl, alkenyl or aryl group; and L is a linking group; and

(3) A succinimide group of the formula:

Wherein R is^zIs an optionally substituted hydrocarbon group and L is a linking group.

16. A salt, composition, method or use according to any preceding claim wherein R⁰is a group of the formula:

Wherein R is⁹、R¹⁰、R¹¹、R¹²Each of which is independently selected from hydrogen or an optionally substituted alkyl, alkenyl or aryl group.

17. A salt, composition, method or use according to any preceding claim wherein X is an optionally substituted alkylene or arylene group.

18. A salt, composition, method or use according to any of claims 1 to 14, 16 or 17, the quaternary ammonium compound being the reaction product of:

(a) Formula R¹R²R³Tertiary amines of N, in which R¹、R²And R³Each of which is independent of the otherAnd is immediately an optionally substituted alkyl group having 1 to 12 carbon atoms;

(b) Epoxides selected from the group consisting of styrene oxide, ethylene oxide, propylene oxide, butylene oxide, hexylene oxide, octylene oxide, stilbene oxide, 2-ethylhexyl glycidyl ether, 1, 2-epoxydodecane, and other alkyl and alkenyl epoxides having from 2 to 50 carbon atoms; and

(c) Formula HOOCXCOO- (R)⁴O)_n-R⁵Wherein X is CH₂CHR or CHRCH₂wherein R is an optionally substituted hydrocarbyl group; and is

n is greater than 1, R⁴Is an ethylene or propylene group and R⁵Is hydrogen; or

n is 0 or and R⁵Is a C1 to C20 alkyl group.

19. A salt, composition, method or use according to any of claims 1 to 14 or 16 to 18, wherein the quaternary ammonium compound is the reaction product of:

(a) Formula R¹R²R³Tertiary amines of N, in which R¹、R²And R³Each of which 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) Formula HOOCXCOO- (R)⁴O)_n-R⁵A compound of (1), which is a compound having C₂₀To C₂₄Reaction products of alkyl or alkenyl substituted succinic acids or anhydrides and an alcohol selected from the group consisting of polypropylene glycol having a number average molecular weight of 300-800, 2-ethylhexanol and butanol.

20. A composition, method or use according to claims 4-19, wherein the composition is a diesel fuel composition.

21. A composition, method or use according to claim 20, wherein the diesel fuel composition comprises one or more further detergents selected from:

(i) A quaternary ammonium salt additive;

(ii) The product of a mannich reaction between an aldehyde, an amine, and an optionally substituted phenol;

(iii) The reaction product of a carboxylic acid-derived acylating agent and an amine;

(iv) The reaction product of a carboxylic acid-derived acylating agent and hydrazine;

(v) Salts formed by the reaction of a carboxylic acid with di-n-butylamine or tri-n-butylamine;

(vi) a reaction product of a hydrocarbyl-substituted dicarboxylic acid or anhydride and an amine compound or salt, the product comprising at least one aminotriazole group; and

(vii) A substituted polyaromatic detergent additive.

22. a composition, method or use according to any of claims 4 to 21, wherein the diesel fuel composition comprises a mixture of two or more quaternary ammonium salt additives.

23. A method or use as defined in any one of claims 7 to 22, wherein the additive is used as a detergent to combat deposits within a diesel fuel composition in a diesel engine.

24. A method or use according to any one of claims 7-23, wherein it is implemented in a modern diesel engine with a high pressure fuel system.

25. A method or use according to any one of claims 7 to 24 which achieves "stay clean" performance.

26. A method or use according to any one of claims 7 to 25 which achieves "clean-up" performance.

27. The method or use according to any one of claims 19-26, wherein the deposit is an injector deposit.

28. A method or use according to claim 27 wherein the deposit is an internal diesel injector deposit.

29. the method or use according to any one of claims 7 to 28, which achieves an improvement in performance selected from one or more of:

-a reduction in power loss of the engine;

-reduction of external diesel injector deposits;

-reduction of internal diesel injector deposits;

-improvement of fuel economy;

-reduction of fuel filter deposits;

-reduction of emissions; and

-an increase in the maintenance interval.

30. A method or use according to claim 29 which provides performance improvements in modern diesel engines having high pressure fuel systems and in conventional diesel engines.

31. Use according to any one of claims 3 to 30, which provides one or more further benefits selected from lubricity benefits, corrosion inhibition and cold flow improvement.

32. The composition of any of claims 1 or 4 to 22, further comprising one or more other additives selected from lubricity improvers, corrosion inhibitors, and cold flow improvers.

33. Use of an ester additive as defined in any preceding claim to reduce the treat rate of one or more other additives selected from lubricity improvers, corrosion inhibitors and cold flow improvers while maintaining performance.

Example 1

Additive a1, a quaternary ammonium salt additive of the invention, was prepared as follows:

(a) A mixture of olefins having 20 to 24 carbon atoms is heated with 1.2 molar equivalents of maleic anhydride. After the reaction was complete, the excess maleic anhydride was removed by distillation. The anhydride number of the substituted succinic anhydride product was measured to be 2.591 mmoleg^-1。

This product was then heated with 1 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.

(b) Reacting 1 molar equivalent of diethylethanolamine with 1.5 molar equivalents of butylene oxide and 6 molar equivalents of water in the presence of the half-ester/half-acid provided in step (a) in toluene at 60 ℃ for 10 hours to form a quaternary ammonium compound. The volatiles were removed in vacuo.

Compounds a2 to a21 detailed in table 1 were prepared by similar methods.

TABLE 1

Compound (I)	R	H-(OR4)n-OR5	Amines as pesticides	Epoxide compound
					A1	C20-24	Polypropylene glycol Mn425	Diethyl ethanolamine	Epoxy butane
A2	C20-24	Polypropylene glycol Mn425	Dimethylethanolamine	Epoxy butane
					A3	C20-24	polypropylene glycol Mn425	Triethylamine	Epoxy butane
A4	C20-24	Polypropylene glycol Mn425	Tributylamine	Epoxy butane
					A5	C20-24	Tripropylene glycol	Dimethylethanolamine	Epoxy butane
A6	C20-24	Tripropylene glycol	Diethyl ethanolamine	Epoxy butane
					A7	C20-24	Tripropylene glycol	Triethylamine	Epoxy butane
A8	C20-24	Tripropylene glycol	Tributylamine	Epoxy butane
					A9	C20-24	Triethylene glycol	Dimethylethanolamine	Epoxy butane
A10	C20-24	Triethylene glycol	Diethyl ethanolamine	Epoxy butane
					A11	C20-24	Triethylene glycol	Triethylamine	Epoxy butane
A12	C20-24	triethylene glycol	Tributylamine	Epoxy butane
					A13	C20-24	Polypropylene glycol Mn725	Dimethylethanolamine	Epoxy butane
A14	C20-24	polypropylene glycol Mn725	Diethyl ethanolamine	epoxy butane
					A15	C20-24	Polypropylene glycol Mn725	Triethylamine	Epoxy butane
A16	C20-24	Polypropylene glycol Mn725	Tributylamine	Epoxy butane
					A17	C20-24	tetraethylene glycol	dimethylethanolamine	Epoxy butane
A18	C20-24	Tetraethylene glycol	Diethyl ethanolamine	Epoxy butane
					A19	C20-24	Tetraethylene glycol	Triethylamine	Epoxy butane
A20	C20-24	Tetraethylene glycol	Tributylamine	Epoxy butane
					A21	C20-24	Polyethylene glycol Mn400	Dimethylethanolamine	Epoxy butane
A22	C20-24	2-Ethyl hexanol	N, N-diethylethanolamine	Epoxy butane
					A23	C20-24	Butanol	n, N-diethylethanolamine	Epoxy butane
A24	C20-24	Poly (ethylene glycol) Mn400	2- [2- (dimethylamino) ethoxy]Ethanol	1, 2-epoxydodecane
					A25	C20-24	Poly (ethylene glycol) Mn400	n, N-dimethylbenzylamine	2-ethylhexyl glycidyl ether
A26	C20-24	Poly (ethylene glycol) Mn400	N, N-dimethylethanolamine	1, 2-epoxydodecane
					A27	C20-24	Poly (ethylene glycol) Mn400	N, N-dimethylethanolamine	Styrene oxide
A28	C20-24	Poly (ethylene glycol) Mn400	N, N-Dimethyloctadecylamine	2-ethylhexyl glycidyl ether
					A29	C20-24	Poly (ethylene glycol) Mn400	N, N-Dimethyloctadecylamine	Epoxy butane
A30	C20-24	Poly (ethylene glycol) Mn400	N, N-Dimethyloctadecylamine	1, 2-epoxydodecane
					A31	C20-24	Poly (ethylene glycol) Mn400	N, N-Dimethyloctadecylamine	Styrene oxide
A32	C20-24	Poly (propylene glycol) Mn425	N, N-dimethylbenzylamine	2-ethylhexyl glycidyl ether
					A33	C20-24	Poly (propylene glycol) Mn425	N, N-dimethylbenzylamine	epoxy butane
A34	C20-24	Poly (propylene glycol) Mn425	N, N-dimethylbenzylamine	Styrene oxide
					A35	C20-24	Poly (propylene glycol) Mn425	n, N-dimethylethanolamine	1, 2-epoxydodecane
A36	C20-24	Poly (propylene glycol) Mn425	N, N-Dimethyloctadecylamine	2-ethylhexyl glycidyl ether
					A37	C20-24	Poly (propylene glycol) Mn425	N, N-Dimethyloctadecylamine	Epoxy butane
A38	C20-24	Poly (propylene glycol) Mn425	n, N-Dimethyloctadecylamine	Styrene oxide
					A39	C20-24	Tetradecanol	N, N-diethylethanolamine	Epoxy butane
A40	C20-24	Tris (propylene glycol)	2- [2- (dimethylamino) ethoxy]ethanol	2-ethylhexyl glycidyl ether
					A41	C20-24	Tris (propylene glycol)	2- [2- (dimethylamino) ethoxy]ethanol	1, 2-epoxydodecane
A42	C20-24	Tris (propylene glycol)	2- [2- (dimethylamino) ethoxy]Ethanol	Styrene oxide
					A43	C20-24	Tris (propylene glycol)	N, N-dimethylbenzylamine	2-ethylhexyl glycidyl ether
A44	C20-24	Tris (propylene glycol)	n, N-dimethylbenzylamine	Epoxy butane
					A45	C20-24	Tris (propylene glycol)	N, N-dimethylbenzylamine	1, 2-epoxydodecane
A46	C20-24	Tris (propylene glycol)	N, N-dimethylbenzylamine	styrene oxide
					A47	C20-24	tris (propylene glycol)	N, N-dimethylethanolamine	1, 2-epoxydodecane
A48	C20-24	Tris (propylene glycol)	N, N-Dimethyloctadecylamine	2-ethylhexyl glycidyl ether
					A49	C20-24	Tris (propylene glycol)	n, N-Dimethyloctadecylamine	Epoxy butane
A50	C20-24	Tris (propylene glycol)	N, N-Dimethyloctadecylamine	1, 2-epoxydodecane
					A51	C20-24	Tris (propylene glycol)	N, N-Dimethyloctadecylamine	Styrene oxide
A52	1000PIB	Tris (propylene glycol)	N, N-dimethylethanolamine	1, 2-epoxydodecane