Substituted Mannich base fuel additives, compositions, and methods

Patent metadata

Field	Value
Publication number	US-10899986-B2
Application number	US-201716324203-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

Mannich base compositions include 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, with (2) an alkyl substituted hydroxyaromatic compound, and (3) and aldehyde. The Mannich base compositions are useful for fuel additives and other articles. 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. A substituted Mannich base composition comprising a reaction product of (1) an amine component comprising at least one multifunctional amine of structure (I):

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 , C 1 -C 21 alkyl, or C 2 -C 21 alkenyl; n is 2; and m is 1 or 2, and (2) an alkyl substituted hydroxyaromatic compound comprising an oligonieric or polymeric alkyl substituent being a polyisobutylene of 250-1500 molecular weight and (3) an aldehyde.

2. The composition of claim 1 , wherein the hydroxyaromatic is selected from the group consisting of phenol, o-cresol, and combinations thereof.

3. The composition of claim 1 , wherein in which the aldehyde component is an aliphatic or aromatic aldehyde of up to 18 carbons.

4. The composition of claim 3 , wherein the aldehyde is formaldehyde or paraformaldehyde.

5. 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.

6. The composition of claim 1 , wherein the amine component comprises a compound wherein R1 is H or CH 2 CH 2 CH 2 NH 2 .

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 50 pbw amine having 4 nitrogen atoms, 40 to 95 pbw amine having 5 nitrogen atoms, and 0 to 50 pbw amine having at least 6 nitrogen atoms.

8. 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 1 to 15 pbw amine having 4 nitrogen atoms, 50 to 90 pbw amine having 5 nitrogen atoms, and 5 to 35 pbw amine having at least 6 nitrogen atoms.

9. The composition of claim 1 , wherein the alkyl substituted hydroxyaromatic component, the aldehyde and amine component are reacted in a ratio of moles of alkyl substituted hydroxyaromatic component to aldehyde to multifunctional amine are from about 0.5-1:0.5-3.5:0.5-2.0.

10. The composition of claim 1 , further comprising at least one compound selected from the group consisting of alkyl substituted phenols, dimethylaminomethylphenol, bis(dimethylaminomethyl)phenol, and tris(dimethylaminomethyl)phenol.

11. The composition of claim 1 , wherein the composition comprises a reaction product of the amine component, the alkyl substituted hydroxyaromatic component, the aldehyde and at least one additional 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.

12. The composition of claim 11 , 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, a Mannich base derivative of an aliphatic amine, a Mannich base derivative of a cycloaliphatic amine, a Mannich base 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.

13. The composition of claim 12 , wherein the at least one multifunctional amine is selected from the group consisting of ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, higher polyethyleneamines, aminoethylpiperazine, 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, N-methyl piperazine, and combinations thereof.

14. A substituted Mannich base fuel additive comprising the composition of claim 1 .

15. A fuel composition comprising fuel and the substituted Mannich base fuel additive of claim 14 .

16. 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 15 .

Assignees

• Evonik Operations Gmbh

Inventors

• Smith Buford Brian
• Vedage Gamini Ananda

Classifications

• C07C209/48 Primary

  by reduction of nitriles · CPC title

• C10L1/238

  obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds {(C10L1/221 takes precedence)} · CPC title

• C10L1/143

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

• C10L1/1616

  fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine · CPC title

• C10L1/1985

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