Ultra-low molecular weight imide containing quaternary ammonium salts having short hydrocarbon tails

Patent metadata

Field	Value
Publication number	US-11254646-B2
Application number	US-201615780785-A
Country	US
Kind code	B2
Filing date	Dec 2, 2016
Priority date	Dec 2, 2015
Publication date	Feb 22, 2022
Grant date	Feb 22, 2022

Abstract

The present technology is related to imide containing quaternary ammonium salts having a hydrocarbyl substituent of number average molecular weight less 300, and additive packages having such quaternary ammonium salts and improved stability.

First claim

What we claim:

1. A composition comprising an imide containing quaternary ammonium salt (“imide quat”), wherein the imide 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 has a number average molecular weight less than 300 and comprises at least one dodecenyl succinic anhydride, dodecenyl succinic acid, hexadecenyl succinic anhydride, hexadecenyl succinic acid, octadecenyl succinic anhydride, octadecenyl succinic acid, or mixtures thereof, and
(ii) a nitrogen containing compound having a nitrogen atom capable of reacting with said hydrocarbyl-substituted acylating agent to form an imide, and further having at least one quaternizable amino group; and

b) a quaternizing agent suitable for converting the quaternizable amino group of the nitrogen containing compound to a quaternary nitrogen.

2. The composition of claim 1 , wherein the quaternizable amino group is a primary, secondary or tertiary amino group.

3. The composition of claim 1 , wherein the quaternizing agent comprises at least one dialkyl sulfate, alkyl halide, hydrocarbyl substituted carbonate, hydrocarbyl epoxide, carboxylate, alkyl ester or mixtures thereof.

4. The composition of claim 1 , further comprising a hydrolyzed alkenyl succinic acid or anhydride with a molecular weight M n ranging from about 225 to about 1000.

5. The composition of claim 4 , wherein the hydrolyzed alkenyl succinic acid or anhydride has a M n of 1000.

6. The composition of claim 5 , wherein the hydrolyzed alkenyl succinic acid or anhydride has a M n of 550.

7. A composition comprising an imide containing quaternary ammonium salt (“imide quat”) and a hydrolyzed alkenyl succinic acid or anhydride with a molecular weight M n ranging from about 225 to about 1000, wherein the imide 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 has a number average molecular weight of less than 300 and comprises at least one dodecenyl succinic anhydride, dodecenyl succinic acid, hexadecenyl succinic anhydride, hexadecenyl succinic acid, octadecenyl succinic anhydride, octadecenyl succinic acid, or mixtures thereof, and
(ii) a nitrogen containing compound having a nitrogen atom capable of reacting with said hydrocarbyl-substituted acylating agent to form an imide, and further having at least one quaternizable amino group; and

b) a quaternizing agent suitable for converting the quaternizable amino group of the nitrogen containing compound to a quaternary nitrogen.

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

9. The composition of claim 8 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.

10. The composition of claim 9 , wherein said low number average molecular weight soap has a number average molecular weight (M n ) of less than 340.

11. The composition of claim 8 , further comprising from 0.01 to 25 ppm of a metal and from 1 to 12 ppm of a corrosion inhibitor.

12. The composition of claim 11 , 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.

13. The composition of claim 9 , wherein the low number average molecular weight PIBSI has an M n of less than 400.

14. A method of reducing and/or preventing injector deposits comprising:
c) 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 an imide quat according to claim 1 therein; and

d) operating said engine.

15. The method of claim 14 , wherein the fuel comprises a low number average molecular weight soap, a low number average molecular weight polyisobutylene succinimide (PIBSI), or mixtures thereof.

16. The method of claim 15 wherein said low number average molecular weight soap has a number average molecular weight (M n ) of less than 340.

17. The method of claim 14 wherein the fuel comprises from 0.01 to 25 ppm of a metal and from 1 to 12 ppm of a corrosion inhibitor.

18. The method of claim 17 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.

19. The method of claim 15 , wherein said low number average molecular weight PIBSI has an M n of less than 400.

Assignees

• Lubrizol Corp

Inventors

• Arters David C
• Moreton David J
• Bush James H
• Stevenson Paul R
• Adams Paul E

Classifications

• C07D307/60 Primary

  Two oxygen atoms, e.g. succinic anhydride · CPC title

• C10L1/2387

  Polyoxyalkyleneamines {(poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C) (C10L1/221 takes precedence)} · CPC title

• C10L1/2437

  Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters · CPC title

• C10L10/04

  for minimising corrosion or incrustation · CPC title

• C10N2020/04

  Molecular weight; Molecular weight distribution · CPC title