Amine alkenyl substituted succinimide reaction product fuel additives, compositions, and methods

Patent metadata

Field	Value
Publication number	US-10899985-B2
Application number	US-201716324147-A
Country	US
Kind code	B2
Filing date	Aug 25, 2017
Priority date	Aug 25, 2016
Publication date	Jan 26, 2021
Grant date	Jan 26, 2021

Abstract

Amine alkenyl substituted succinimide reaction product compositions including the reaction products of (1) an amine component including at least one multifunctional amine of structure (1):

wherein each R is independently H or CH 2 CH 2 CH 2 NH 2 ; R 1 is H, CH 2 CH 2 CH 2 NH 2 , C1-C21 alkyl, or C2-C21 alkenyl; n is 2; and m is 1 or 2 and (2) an alkenyl substituted anhydride. Additive compositions, fuel additives, fuel compositions and methods for reducing deposit formations in a fuel system are also disclosed.

First claim

The invention claimed is:

1. An amine alkenyl substituted succinimide reaction product composition comprising a reaction product of (1) an amine component comprising at least one multifunctional amine of structure (I):

where each R is independently H or CH 2 CH 2 CH 2 NH 2 ; R 1 is H, CH 2 CH 2 CH 2 NH 2 , C1-C21 alkyl, or C2-C21 alkenyl; n is 2; and m is 1 or 2 and (2) an alkenyl substituted anhydride comprising an oligomeric or polymeric alkenyl substituent being a polyisobutylene of 300-2000 molecular weight.

2. The composition of claim 1 , wherein the alkenyl substituted anhydride is maleic anhydride.

3. The composition of claim 1 , wherein in which the alkenyl substituted anhydride is an aliphatic or aromatic carboxylic acid or anhydride of up to 18 carbons.

4. The composition of claim 1 , wherein the amine component comprises a compound selected from the group consisting of N-3-aminopropyl diethylenetriamine; N-3-aminopropyl-[N′-3-[N-3-aminopropyl]aminopropyl]diethylenetriamine; N,N′-bis(3-aminopropyl)diethylenetriamine; N,N-bis(3-aminopropyl)diethylenetriamine; N,N,N′-tris(3-aminopropyl)diethylenetriamine; N,N′,N″-tris(3-aminopropyl)diethylenetriamine; N,N,N′,N′-tetrakis(3-aminopropyl)diethylenetriamine; N,N-bis(3-aminopropyl)-[N′-3-[N-3-aminopropyl]aminopropyl]-[N′-3-aminopropyl]diethylenetriamine; N-3-aminopropyl-[N′-3-[N-3-aminopropyl]aminopropyl]-[N′-3-aminopropyl]diethylenetriamine; and combinations thereof.

5. The composition of claim 1 , wherein R1 is H or CH 2 CH 2 CH 2 NH 2 .

6. The composition of claim 1 , wherein the amine component comprises a mixture of amines of structure according to formula (I) in a parts-by-weight (pbw) ratio of 0 to 50 pbw amine having 4 nitrogen atoms, 40 to 95 pbw amine having 5 nitrogen atoms, 0 to 50 pbw amine having at least 6 nitrogen atoms.

7. The composition of claim 1 , wherein the amine component comprises a mixture of amines of structure according to formula (I) in a parts-by-weight (pbw) ratio of 0 to 20 pbw amine having 4 nitrogen atoms, 50 to 95 pbw amine having 5 nitrogen atoms, 3 to 35 pbw amine having at least 6 nitrogen atoms.

8. The composition of claim 1 , wherein the amine component and the alkenyl anhydride component are reacted in a ratio of moles of alkenyl anhydride component to multifunctional amine are from about 0.5-3:0.5-1.0.

9. The composition of claim 1 , wherein the composition comprises a reaction product of the amine component, the alkenyl anhydride and (3) at least one additional multifunctional amine, the multifunctional amine having three or more active amine hydrogens or an amine having at least one primary and/or secondary amine as well as at least one tertiary amine.

10. The composition of claim 9 , wherein the at least one multifunctional amine is selected from the group consisting of an aliphatic amine, a cycloaliphatic amine, an aromatic amine, a poly(alkylene oxide) diamine or triamine, an alkenyl succinimide derivative of an aliphatic amine, an alkenyl succinimide derivative of a cycloaliphatic amine, an alkenyl succinimide derivative of an aromatic amine, an amine adduct derivative of an aliphatic amine with a glycidyl ether, an amine adduct derivative of a cycloaliphatic amine with a glycidyl ether, or an amine adduct derivative of an aromatic amine with a glycidyl ether, and the like, and combinations thereof.

11. The composition of claim 9 , wherein the at least one multifunctional amine is selected from the group consisting of ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, higher polyethyleneamines, am inoethylpiperazine, meta-xylylenediamine, the various isomers of diamine-cyclohexane, isophorone diamine, 3,3′-dimethyl-4,4′-diaminodicyclohexyl methane, 4,4′-diaminodicyclohexyl methane, 2,4′-diaminodicyclohexyl methane, the mixture of methylene bridged poly(cyclohexyl-aromatic)amines, 1,2-propylenediamine, 1,3-propylenediamine, 1,4-butanediamine, 1,5-pentanediamine, 1,3-pentanediamine, 1,6-hexanediamine, 3,3,5-trimethyl-1,6-hexane-diamine, 3,5,5-trimethyl-1,6-hexanediamine, 2-methyl-1,5-pentanediamine, bis-(3-amino-propyl)amine, N,N′-bis-(3-aminopropyl)-1,2-ethanediamine, N-(3-aminopropyl)-1,2-ethanediamine, 1,2-diaminocyclohexane, 1,3-diaminocyclohexane, 1,4-diamino-cyclohexane, the poly(alkylene oxide)diamines and triamines, aminopropylated ethylene glycols, aminopropylated propanediols, aminopropylated butanediols, aminopropylated hexanediols, aminopropylated polyethylene glycols, aminopropylated polypropylene glycols, aminopropylated polybutanediols, N,N-dimethyl-1,3-propanediamine, and N-methyl piperazine.

12. An alkenyl succinimide fuel additive dispersant/detergent comprising the composition of claim 1 .

13. A fuel composition comprising fuel and the alkenyl succinimide fuel additive of claim 12 .

14. A method to reduce deposit formation in a fuel system of an internal combustion engine comprising operating the internal combustion system with a fuel according to claim 13 .

Assignees

• Evonik Operations Gmbh

Inventors

• Smith Buford Brian
• Vedage Gamini Ananda

Classifications

• C10L1/143 Primary

  mixtures of organic macromolecular compounds with organic non-macromolecular compounds · CPC title

• C10L1/1985

  polyethers, e.g. di- polygylcols and derivatives; ethers - esters · CPC title

• C08C19/22

  Incorporating nitrogen atoms into the molecule · CPC title

• C10N2030/04

  Detergent property or dispersant property · CPC title

• C10M2217/06

  Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound · CPC title