Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants

Patent metadata

Field	Value
Publication number	US-9255236-B2
Application number	US-201414337307-A
Country	US
Kind code	B2
Filing date	Jul 22, 2014
Priority date	Jul 6, 2010
Publication date	Feb 9, 2016
Grant date	Feb 9, 2016

Abstract

The present invention relates to novel acid-free quaternized nitrogen compounds, to the preparation thereof and to the use thereof as a fuel and lubricant additive, more particularly as a detergent additive, as a wax antisettling additive (WASA) or as an additive for reducing internal diesel injector deposits (IDID); to additive packages which comprise these compounds; and to fuels and lubricants thus additized. The present invention further relates to the use of these acid-free quaternized nitrogen compounds as a fuel additive for reducing or preventing deposits in the injection systems of direct-injection diesel engines, especially in common-rail injection systems, for reducing the fuel consumption of direct-injection diesel engines, especially of diesel engines with common-rail injection systems, and for minimizing power loss in direct-injection diesel engines, especially in diesel engines with common-rail injection systems.

First claim

The invention claimed is:

1. A method for reducing or preventing deposits in an injection system of a diesel engine, the method comprising adding a deposit reducing or deposit preventing effective amount of a quaternized nitrogen compound to a diesel engine in need thereof, wherein said quaternized nitrogen compound is a quaternized nitrogen compound prepared by a process comprising:
a) reacting an anhydride compound derived from a polycarboxylic acid, or a dimeric form thereof having two acid anhydride groups, with a compound comprising (i) a group comprising oxygen or nitrogen wherein the group is reactive with an anhydride, and (ii) a quaternizable amino group, to form a product, and
b) quaternizing the product from a) to obtain the quaternized nitrogen compound,
wherein the anhydride compound comprises a hydrocarbyl substituent having a number-average molecular weight (Mn) in a range from about 200 to 20 000;
wherein the quaternized nitrogen compound has a formula selected from the group consisting of formulae Ia-1, Ia-2, Ia-3, Ib-1, Ib-2 and Ib-3:

in which R 1 is H or a straight-chain or branched hydrocarbyl radical which may optionally be mono- or polysubstituted by hydroxyl, carboxyl, hydrocarbyloxy and/or an acyl radical, or has one or more ether groups in a hydrocarbyl chain;
R 2 is H or alkyl;
R 3 is hydrocarbyl;
at least one of R 4 , R 5 and R 6 is a radical introduced by quaternization, and any of R 4 , R 5 and R 6 that are radicals not introduced by quaternization are straight-chain or branched, cyclic hydrocarbyl radicals which are optionally mono- or polysubstituted and optionally have one or more heteroatoms;
R 7 is H or a straight-chain or branched hydrocarbyl radical which may optionally be mono- or polysubstituted by hydroxyl, carboxyl, hydrocarbyloxy and/or an acyl radical, or has one or more ether groups in a hydrocarbyl chain, or R 7 together with one of R 4 , R 5 and R 6 forms a bridge group;
L 1 is a chemical bond or a straight-chain or branched alkylene group; and
L 2 is a straight-chain or branched alkylene group which optionally bears one or more heteroatoms or substituents.

2. The method of claim 1 , wherein said method is for preventing or reducing internal diesel injector deposits of a direct injection diesel engine.

3. The method of claim 1 , wherein said method is for preventing or reducing flow restriction in an indirect injection diesel engine as determined by the XUD 9 test method.

4. The process of claim 1 , wherein the anhydride compound is a di-, tri- or tetracarboxylic anhydride.

5. The process of claim 1 , wherein the anhydride compound is an anhydride of a C 4 -C 10 -dicarboxylic acid.

6. The process of claim 1 , wherein the anhydride compound comprises a hydrocarbyl substituent having a number-average molecular weight (Mn) in a range from about 200 to 10 000.

7. The process of claim 1 , wherein the compound reactive with an anhydride is
a) a hydroxyalkyl-substituted mono- or polyamine having at least one quaternizable primary, secondary or tertiary amino group;
b) a straight-chain or branched, cyclic, heterocyclic, aromatic or nonaromatic polyamine having at least one primary or secondary amino group and having at least one quaternizable primary, secondary or tertiary amino group; or
c) a piperazine.

8. The process of claim 7 , wherein the compound reactive with an anhydride is
a) a hydroxyalkyl-substituted primary, secondary or tertiary monoamine, or a hydroxyalkyl-substituted primary, secondary or tertiary diamine, or
b) a straight-chain or branched aliphatic diamine having two primary amino groups; a di- or polyamine having at least one primary and at least one secondary amino group; a di- or polyamine having at least one primary and at least one tertiary amino group; an aromatic carbocyclic diamine having two primary amino groups; an aromatic heterocyclic polyamine having two primary amino groups; or an aromatic or nonaromatic heterocycle having one primary and one tertiary amino group.

9. The process of claim 1 , wherein the quaternizing agent is an epoxide.

10. The process of claim 9 , wherein the quaternizing is performed without adding an H+ donor.

11. The process of claim 1 , wherein the reacting a) is performed at a temperature of less than about 80° C.

12. The process of claim 1 , wherein the reacting a) is performed over a period of 1 to 120 minutes.

13. The process of claim 1 , wherein the quaternizing b) is performed at a temperature in a range from 40 to 80° C.

14. The process of claim 1 , wherein the quaternizing b) is performed over a period of 1 to 10 hours.

15. The process of claim 1 , wherein the quaternizing b) is performed with a hydrocarbyl epoxide as a quaternizing agent in the absence of free acid.

16. The process of claim 1 , wherein the reacting a), the quaternizing b), or both, is carried out in the absence of an organic protic solvent.

Assignees

• Basf Se

Inventors

• Grabarse Wolfgang
• Boehnke Harald
• Tock Christian
• Roeger-Goepfert Cornelia
• Voelkel Ludwig

Classifications

• C10N2040/25

  Internal-combustion engines · CPC title

• C10N2020/04

  Molecular weight; Molecular weight distribution · CPC title

• C10N2030/04

  Detergent property or dispersant property · CPC title

• C10M2215/28

  Amides; Imides · CPC title

• C10M2203/1045

  used as base material · CPC title