# US 2019/0169515 A1 · Substituted mannich base fuel additives, compositions, and methods

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2019/0169515 A1
- Document ID: US20190169515A1
- Status: Published application
- Kind: A1
- Application number: 16/324,203
- Filed: 2017-08-25
- Published: 2019-06-06
- Earliest claimed: 2016-08-25
- Assignees: Evonik Degussa GmbH
- Applicants: Evonik Degussa GmbH
- Inventors: Buford Brian Smith; Gamini Ananda Vedage
- Web page: https://patentgrep.com/patent/US20190169515A1

## CPC

- C10L 1/236: obtained by reactions involving only carbon-to-carbon unsaturated bonds {derivatives thereof (C10L1/221 takes precedence)}
- C07C 209/48: by reduction of nitriles
- C07C 253/30: by reactions not involving the formation of cyano groups
- C08C 19/22: Incorporating nitrogen atoms into the molecule
- C08F 132/06: having two or more carbon-to-carbon double bonds
- C10L 1/143: {mixtures of organic macromolecular compounds with organic non-macromolecular compounds}
- C10L 1/238: obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds {(C10L1/221 takes precedence)}
- C10L 10/04: for minimising corrosion or incrustation
- C10L 10/06: for facilitating soot removal
- C10L 1/1616: {fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine}
- C10L 1/1985: {polyethers, e.g. di- polygylcols and derivatives; ethers - esters}
- C10L 2200/0423: Gasoline
- C10L 2270/023: for gasoline engines
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08C: TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## 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 CH2CH2CH2NH2; R1 is H, CH2CH2CH2NH2, 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.

## Claims

### Claim 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 CH2CH2CH2NH2; R1 is H, CH2CH2CH2NH2, C1-C21 alkyl, or C2-C21 alkenyl; n is 2; and m is 1 or 2, and (2) an alkyl substituted hydroxyaromatic compound and (3) an aldehyde.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the alkyl substituted hydroxyaromatic component comprises an oligomeric or polymeric alkyl substituent.

### Claim 3 (depends on 2)

The composition of claim 2, wherein the alkyl substituent is a polyisobutylene of 250-1500 molecular weight.

### Claim 4 (depends on 2)

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

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 5)

The composition of claim 5, wherein the aldehyde is formaldehyde or paraformaldehyde.

### Claim 7 (depends on 1)

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.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the amine component comprises a compound wherein R1 is H or CH2CH2CH2NH2.

### Claim 9 (depends on 1)

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.

### Claim 10 (depends on 1)

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.

### Claim 11 (depends on 1)

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.

### Claim 12 (depends on 1)

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.

### Claim 13 (depends on 1)

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.

### Claim 14 (depends on 13)

The composition of claim 13, 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.

### Claim 15 (depends on 14)

The composition of claim 14, 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.

### Claim 16

A substituted Mannich base composition comprising a reaction product of (1) an amine component comprising at least one multifunctional amine of structure (II):
where R1 and R3 is H in structure (II) while R2 and R4 are CH2CH2CH2NH2 and (2) an alkyl substituted hydroxyaromatic compound and (3) an aldehyde.

### Claim 17 (depends on 1)

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

### Claim 18 (depends on 17)

A fuel composition comprising fuel and the substituted Mannich base fuel additive of claim 17.

### Claim 19 (depends on 18)

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 18.

### Claim 20 (depends on 16)

A substituted Mannich base fuel additive comprising the composition of claim 16.

### Claim 21 (depends on 20)

A fuel composition comprising fuel and the substituted Mannich base fuel additive of claim 20.

### Claim 22 (depends on 21)

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 21.