Coupled quaternary ammonium salts

Patent metadata

Field	Value
Publication number	US-2017101594-A1
Application number	US-201515315153-A
Country	US
Kind code	A1
Filing date	May 29, 2015
Priority date	May 30, 2014
Publication date	Apr 13, 2017
Grant date	—

Abstract

The present technology is related to coupled quaternary ammonium salts, and the use of such coupled quaternary ammonium salts in fuel and oil compositions, or demulsification and/or engine performance of the compositions.

First claim

1 . A composition comprising a coupled amine containing quaternary ammonium salt (“coupled amine quat”), wherein the coupled amine quat comprises the reaction product of:
a) a quaternizable compound that is the reaction product of:
(i) a hydrocarbyl-substituted acylating agent, wherein the hydrocarbyl-substituent of the hydrocarbyl-substituted acylating agent has a number average molecular weight ranging from 100 to 5000, and
(ii) a nitrogen containing compound having an oxygen or nitrogen atom capable of reacting with said hydrocarbyl-substituted acylating agent and further having at least one quaternizable amino group; and

b) a quaternizing agent capable of coupling more than one quaternizable compound of (a).

2 . (canceled)

3 . (canceled)

4 . The composition of any previous claim 1 , wherein the ratio of the quaternizable compound of a) to the quaternizing agent of b) is from about 2:1 to about 1:1.

5 . The composition of claim 1 , wherein the quaternizing agent comprises at least one polyepoxides, polyhalides, epoxy halides, aromatic polyesters, or mixtures thereof

6 . The composition of claim 1 , wherein the quaternizing agent comprises di-epoxides or akyl di-halides.

7 . The composition of claim 1 , wherein the quaternizing agent comprises 1,4 butanediol diglycidylether, or bisphenol-A-diglycidylether.

8 . The composition of claim 1 , wherein the at least one quaternizable amino group is a primary, secondary or tertiary amino group.

9 . The composition of claim 1 wherein the nitrogen containing compound containing the at least one quaternizable amine group is a polyamine or polyol.

10 . The composition of claim 1 wherein the nitrogen containing compound containing the at least one quaternizable amine group is 3,3′-diamino-N-methyldipropylamine.

11 . The composition of claim 1 , wherein the hydrocarbyl-substituted acylating agent comprises at least one polyisobutenyl succinic anhydride or polyisobutenyl succinic acid.

12 . The composition of claim 1 , wherein the reaction in a) is carried out at a temperature of greater than 80° C.

13 . The composition of claim 1 , wherein the reaction in a) is carried out at a temperature of less than 80° C.

14 . The composition of claim 1 , wherein the quaternizing agent is employed in the presence of a protic solvent.

15 . The composition of claim 14 , wherein the protic solvent comprises 2-ethylhexanol, water, and mixtures thereof

16 . The composition of claim 1 , wherein the quaternizing agent is employed in the presence of an acid.

17 . The composition of claim 16 , wherein the acid is present in the structure of the acylating agent.

18 . The composition of claim 1 , further comprising at least one other additive.

19 . The composition of claim 18 , wherein the at least one other additive comprises a detergent, a dispersant, a demulsifier, a lubricity agent, a cold flow improver, an antioxidant, or a mixture thereof.

20 . The composition of claim 18 , wherein the at least one other additive comprises at least one hydrocarbyl-substituted succinic acid.

21 . The composition of claim 18 , wherein the at least one other additive comprises at least one hydrocarbyl-substituted quaternary ammonium salt.

22 . The composition of claim 18 , wherein the at least one other additive comprises at least one detergent/dispersant that is an amphiphilic substance which possess at least one hydrophobic hydrocarbon radical with a number average molecular weight of 100 to 10000 and at least one polar moiety selected from (i) Mono- or polyamino groups having up to 6 nitrogen atoms, at least one nitrogen atom having basic properties; (ii) Hydroxyl groups in combination with mono or polyamino groups, at least one nitrogen atoms having basic properties; (v) Polyoxy-C 2 to C 4 alkylene moieties terminated by hydroxyl groups, mono- or polyamino groups, at least one nitrogen atom having basic properties, or by carbamate groups; (vii) Moieties derived from succinic anhydride and having hydroxyl and/or amino and/or amido and/or imido groups; and/or (viii) Moieties obtained by Mannich reaction of substituted phenols with aldehydes and mono-or polyamines.

23 . The composition of claim 20 , wherein the hydrocarbyl-substituent is a polyisobutylene having a molecular weight ranging from 100 to 5000.

24 . The composition of claim 18 , wherein the at least one other additive comprises at least one Mannich compound.

25 . The composition of claim 1 , further comprising a fuel that is liquid at room temperature.

26 . The composition of claim 25 , wherein the fuel is gasoline or diesel.

27 . The fuel composition of claim 25 further comprising at least one of a low number average molecular weight soap, a low number average molecular weight polyisobutylene succinimide (PIBSI), or a mixture thereof.

28 . The fuel composition of claim 27 , comprising a low number average molecular weight soap with a number average molecular weight (M n ) of less than 340.

29 . The fuel composition of claim 27 , further comprising from 0.01 to 25 ppm of a metal and from 1 to 12 ppm of a corrosion inhibitor.

30 . The fuel composition of claim 29 , wherein the corrosion inhibitor is an alkenyl succinic acid comprising at least one of dodecenyl succinic acid (DDSA), hexadecenyl succinic acid (HDSA), or mixtures thereof.

31 . The fuel composition of claim 27 , wherein the fuel comprises PIBSI with a low number average molecular weight M n of less than 400.

32 . A method of improving water shedding performance of a fuel composition comprising adding a composition comprising a coupled quat according to claim 24 to said fuel.

33 . The composition of any of claim 1 , further comprising an oil of lubricating viscosity.

34 . A method of operating an internal combustion engine comprising:
c) supplying to said engine:
(i) a fuel, wherein said fuel
1. is liquid at room temperature; and
2. has a composition comprising a coupled quat according to claim 1 therein; and

d) operating said engine.

35 . A method of operating an internal combustion engine comprising:
e) supplying to a crankcase of said engine:
(i) an oil of lubricating viscosity having a composition comprising a coupled quat according to any claim 1 therein, and
f) operating said engine.

36 . The method of claim 35 wherein the oil of lubricating viscosity has total sulfated ash content of less than 1 wt % and/or a phosphorus content of less than 0.11 wt %.

37 . A method of reducing and/or preventing injector deposits comprising:
g) supplying to a fuel injector of said engine:
(i) a fuel, wherein said fuel
1. is liquid at room temperature; and
2. has a composition comprising a coupled quat according to claim 1 therein; and

h) operating said engine.

38 . The method of claim 37 , wherein the deposits comprise a low number average molecular weight soap, a low number average molecular weight polyisobutylene succinimide (PIBSI), or mixtures thereof

39 . The method of claim 38 wherein the fuel comprises a low number average molecular weight soap with a number average molecular weight (M n ) of less than 340.

Assignees

• Lubrizol Corp

Inventors

• Stevenson Paul R
• Bush James H
• Moreton David J

Classifications

• C10N2030/24

  Emulsion properties · CPC title

• C10N2040/26

  Two-strokes {or two-cycle engines} · CPC title

• C10L2270/026

  for diesel engines, e.g. automobiles, stationary, marine · CPC title

• C10N2040/25

  Internal-combustion engines · CPC title

• C10N2030/04

  Detergent property or dispersant property · CPC title