Additives for fuel oils

Patent metadata

Field	Value
Publication number	US-10308593-B2
Application number	US-63479609-A
Country	US
Kind code	B2
Filing date	Dec 10, 2009
Priority date	Mar 18, 2009
Publication date	Jun 4, 2019
Grant date	Jun 4, 2019

Abstract

A fuel oil composition comprising a major amount of a fuel oil and a minor amount of a compound being the product of the 1,4-addition reaction of (i) ammonia, a primary or secondary hydrocarbyl-substituted amine or a mixture thereof to (ii) a species containing one or more α,β-unsaturated carbonyl groups, wherein the compound includes at least one hydrocarbyl group containing at least 10 carbon atoms. The fuel oil composition has improved low temperature properties.

First claim

What is claimed is:

1. A fuel oil composition comprising (a) a major amount of a fuel oil; and (b) 10-500 ppm by weight based on the weight of the fuel oil of a compound being the product of the 1,4-addition reaction of (i) ammonia, a primary or secondary hydrocarbyl-substituted amine or a mixture thereof to (ii) a species containing one or more α,β-unsaturated carbonyl groups, wherein the compound includes at least one hydrocarbyl group containing at least 10 carbon atoms; and
wherein species (ii) is of formula A-B,
wherein A comprises a moiety of general formula I which is bonded to B via the carbonyl group:

wherein R 3 represents hydrogen, C 1 to C 8 hydrocarbyl group, or C(O)OR 5 ,
wherein R 4 represents C 1 to C 8 hydrocarbyl group, or —C(O)OR 5 , where R 5 represents a hydrocarbyl group, containing from 1 to 40 carbon atoms,
wherein B independently represents —NR 6 R 7 or —OR 8 ,
wherein R 6 and R 7 each independently represent hydrogen or a hydrocarbyl group, containing up to 40 carbon atoms which group is optionally substituted or terminated with one or more substituents selected from —OR 9 , —NR 10 R 11 , or a combination thereof, and/or interrupted by one or more oxygen atoms and/or —N(R 12 )— groups, where R 9 , R 10 , R 11 and R 12 each independently represent hydrogen, a hydrocarbyl group containing up to 20 carbon atoms, or a moiety of general formula I; and,
wherein R 8 independently represents hydrogen or a hydrocarbyl group, containing up to 40 carbon atoms which group is optionally substituted or terminated with one or more substituents of —NR 14 R 15 , and/or interrupted by one or more —N(R 16 )— groups, where R 14 , R 15 and R 16 each independently represent hydrogen, a hydrocarbyl group containing up to 20 carbon atoms, or a moiety of general formula I as defined herein.

2. The fuel oil composition according to claim 1 wherein species (ii) comprises an α,β-unsaturated amide or, an α,β-unsaturated ester.

3. The fuel oil composition according to claim 2 wherein species (ii) comprises an acrylamide, a methacrylamide, an acrylic acid ester, a methacrylic acid ester, a crotonoic acid ester, a fumaric acid ester or a maleic acid ester.

4. The fuel oil composition according to claim 1 wherein species (ii) contains two or more α,β-unsaturated carbonyl groups.

5. The fuel oil composition according to claim 1 wherein (i) is of the formula NHR 1 R 2 , where R 1 independently represents a hydrocarbyl group containing from 8 to 40 carbon atoms, and R 2 independently represents hydrogen or a hydrocarbyl group containing up to 40 carbon atoms.

6. The fuel oil composition wherein the compound according to claim 1 is reacted with (iii) a hydrocarbyl compound containing one or more hydroxy, primary or secondary amino functional groups.

7. The fuel oil composition according to claim 1 further comprising one or more of an ethylene-unsaturated ester copolymer, a comb polymer, an alkyl-phenol formaldehyde condensate, a hydroxy-benzoate formaldehyde condensate and a hydrocarbon polymer.

8. An additive composition comprising a compound as defined in claim 1 and a compatible solvent therefor.

9. The fuel oil composition according to claim 1 further comprising a fuel oil detergent.

10. The fuel oil composition according to claim 1 wherein R 5 represents an alkyl group.

11. The fuel oil composition according to claim 1 wherein R 6 and R 7 each independently represent hydrogen or an alkyl group.

12. The fuel oil composition according to claim 1 wherein R 8 independently represents hydrogen or an alkyl group.

13. The fuel oil composition according to claim 5 wherein R 1 independently represents an alkyl group.

14. The fuel oil composition according to claim 5 wherein R 2 independently represents hydrogen or an alkyl group.

15. A fuel oil composition comprising (a) a major amount of a fuel oil; and (b) 10-500 ppm by weight based on the weight of the fuel oil of a compound being the product of the 1,4-addition reaction of (i) an amine represented by the formula NHR 1 R 2 , where R 1 and R 2 each independently represent hydrogen or a hydrocarbyl group which group is optionally terminated with one or more substituents selected from —OH or —NH 2 and/or interrupted by one or more oxygen atoms or —N(H)— groups to (ii) a species represented by general formula Ill

wherein R 3 represents hydrogen or a C 1 to C 8 hydrocarbyl group, wherein R 4 represents —C(O)OR 5 , where R 5 and R 8 independently represent a hydrocarbyl group containing from 1 to 40 carbon atoms.

Assignees

• Jackson Graham
• Infineum Int Ltd

Inventors

• Jackson Graham

Classifications

• C10L1/2383

  Polyamines or polyimines, or derivatives thereof {(poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C) (C10L1/221 takes precedence)} · CPC title

• C10L1/223

  having at least one amino group bound to an aromatic carbon atom {(C10L1/221, C10L1/2227 take precedence)} · CPC title

• C10L1/2225

  hydroxy containing (C10L1/221 takes precedence) · CPC title

• C07C237/08 Primary

  having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms · CPC title

• C10L1/1981

  Condensation polymers of aldehydes or ketones · CPC title