# US 2021/0277320 A1 · Compositions, Uses and Methods for Improving The Low Temperature Properties of a Middle Distillate Fuel > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2021/0277320 A1 - Document ID: US20210277320A1 - Status: Published application - Kind: A1 - Application number: 17/255,906 - Filed: 2019-07-01 - Published: 2021-09-09 - Earliest claimed: 2018-07-02 - Assignees: Innospec Limited - Applicants: Innospec Limited - Inventors: Torsten Meyer - Web page: https://patentgrep.com/patent/US20210277320A1 ## CPC - C10L 10/14: for improving low temperature properties - C10L 1/143: {mixtures of organic macromolecular compounds with organic non-macromolecular compounds} - C10L 1/146: {Macromolecular compounds according to different macromolecular groups, mixtures thereof} - C10L 1/1966: {poly-carboxylic} - C10L 1/1973: {mono-carboxylic} - C10L 1/2383: Polyamines or polyimines, or derivatives thereof {(poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C) (C10L1/221 takes precedence)} - C10L 10/04: for minimising corrosion or incrustation - C10L 1/1616: {fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine} - C10L 1/2222: {(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates (C10L1/221 takes precedence)} - C10L 1/224: Amides; Imides {carboxylic acid amides, imides (C10L1/221, C10L1/2227 take precedence)} - C10L 1/226: containing at least one nitrogen-to-nitrogen bond, e.g. azo compounds, azides, hydrazines {(C10L1/221 takes precedence)} - C10L 1/232: containing nitrogen in a heterocyclic ring {(C10L1/221 takes precedence)} - C10L 1/238: obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds {(C10L1/221 takes precedence)} - C10L 2200/0446: Diesel - C10L 2200/0476: Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel - C10L 2230/14: for improving storage or transport of the fuel - C10L 2270/026: for diesel engines, e.g. automobiles, stationary, marine - 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 ## Abstract A method of improving the low temperature properties of a middle distillate fuel composition comprising: (a) a nitrogen-containing dispersant; and (b) one or more low temperature property enhancers which are not fumarate vinyl ester copolymers and which are selected from (x) wax antisettling additives; (y) middle distillate flow improvers and mixtures thereof; the method comprising adding to the fuel an additive (c) which is a copolymer comprising units of formula (A): and units of formula (B): wherein R is an alkyl group and each of R1 and R2 is an alkyl group. ## Claims ### Claim 1 A method of improving the low temperature properties of a middle distillate fuel composition comprising: (a) a nitrogen-containing dispersant; and (b) one or more low temperature property enhancers which are not fumarate vinyl ester copolymers and which are selected from (x) wax antisettling additives; (y) middle distillate flow improvers and mixtures thereof; the method comprising adding to the fuel an additive (c) which is a copolymer comprising units of formula (A): and units of formula (B): wherein R is an alkyl group and each of R1 and R2 is an alkyl group. ### Claim 2 (canceled) ### Claim 3 An additive composition for improving the low temperature properties of a middle distillate fuel composition the additive composition comprising: (a) a nitrogen-containing dispersant; (b) one or more low temperature property enhancers which are not fumarate vinyl ester copolymers and which are selected from (x) wax antisettling additives (y) middle distillate flow improvers and mixtures thereof; and (c) a copolymer comprising units of formula (A): and units of formula (B): wherein R is an alkyl group and each of R1 and R2 is an alkyl group. ### Claim 4 A middle distillate fuel composition comprising: (a) a nitrogen-containing dispersant; (b) one or more low temperature property enhancers which are not fumarate vinyl ester copolymers and which are selected from (x) wax antisettling additives; (y) middle distillate flow improvers and mixtures thereof; and (c) a copolymer comprising units of formula (A): and units of formula (B): wherein R is an alkyl group and each of R1 and R2 is an alkyl group. ### Claim 5 (depends on 1) The method according to claim 1 wherein additive (c) is prepared by copolymerising vinyl ester monomers and dialkyl fumarate monomers. ### Claim 6 (depends on 1) The method according to claim 1 wherein R is methyl. ### Claim 7 (depends on 1) The method according to claim 1 wherein each of R1 and R2 is an alkyl group having less than 18 carbon atoms. ### Claim 8 (depends on 1) The method according to claim 1 wherein component (a) is selected from: (i) a quaternary ammonium salt additive; (ii) the product of a Mannich reaction between an aldehyde, an amine and an optionally substituted phenol; (iii) the reaction product of a carboxylic acid-derived acylating agent and an amine; (iv) the reaction product of a carboxylic acid-derived acylating agent and hydrazine; (v) a salt formed by the reaction of a carboxylic acid with di-n-butylamine or tri-n-butylamine; (vi) the reaction product of a hydrocarbyl-substituted dicarboxylic acid or anhydride and an amine compound or salt which product comprises at least one amino triazole group; and (vii) a polyalkylene substituted amine. ### Claim 9 (depends on 1) The method according to claim 1 wherein component (a) is selected from: (i) a quaternary ammonium salt additive; (ii) the product of a Mannich reaction between an aldehyde, an amine and an optionally substituted phenol; and (iii) the reaction product of a carboxylic acid-derived acylating agent and an amine. ### Claim 10 (depends on 1) The method according to claim 1 wherein component (a) is selected from one or more of: a quaternary ammonium salt additive formed by reacting methyl salicylate or dimethyl oxalate with the reaction product of a polyisobutylene-substituted succinic anhydride having a PIB number average molecular weight of 700 to 1300 and dimethylaminopropylamine; the Mannich reaction product of dodecylphenol, formaldehyde and either ethylene diamine or tetraethylpentamine; and the reaction product of a polyisobutenyl substituted succinic acid/anhydride having a PIB molecular weight (Mn) of 500 to 1300 and a polyethylene polyamine having 1 to 9 amino groups and 1 to 8 ethylene groups. ### Claim 11 (depends on 1) The method according to claim 1 wherein component (b) comprises at least one wax antisettling additive (x) and at least one middle distillate flow improver (y). ### Claim 12 (depends on 1) The method according to claim 1 wherein component (b) comprises a wax antisettling additive (x) which is the reaction product of (I) a compound containing the segment —NR3R4 where R3 represents a group containing from 4 to 44 carbon atoms and R4 represents a hydrogen atom or a group R3, and (II) a carboxylic acid having from 1 to 4 carboxylic acid groups or a reactive equivalent thereof. ### Claim 13 (depends on 1) The method according to claim 1 wherein component (b) comprises a wax antisettling additive (x) which is the reaction product of di(hydrogenated) tallow amine (I) and phthalic acid or its acid anhydride (II). ### Claim 14 (depends on 1) The method according to claim 1 wherein component (b) comprises a middle distillate flow improver (y) which is a copolymer of ethylene and an olefinically unsaturated compound. ### Claim 15 (depends on 1) The method according to claim 1 wherein component (b) comprises a middle distillate flow improver (y) which, in addition to ethylene, contains 1 to 23 mol %, of olefinically unsaturated compounds as co-monomers. ### Claim 16 (canceled) ### Claim 17 (depends on 3) The composition according to claim 3 wherein additive (c) is prepared by copolymerising vinyl ester monomers and dialkyl fumarate monomers. ### Claim 18 (depends on 3) The composition according to claim 3 wherein R is methyl. ### Claim 19 (depends on 3) The composition according to claim 3 wherein each of R1 and R2 is an alkyl group having less than 18 carbon atoms. ### Claim 20 (depends on 4) The composition according to claim 4 wherein additive (c) is prepared by copolymerising vinyl ester monomers and dialkyl fumarate monomers. ### Claim 21 (depends on 4) The composition according to claim 4 wherein R is methyl. ### Claim 22 (depends on 4) The composition according to claim 4 wherein each of R1 and R2 is an alkyl group having less than 18 carbon atoms.