Classifications

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  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
  • C10L10/16—Pour-point depressants
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/14—Organic compounds
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
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  • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
  • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
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  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
  • C10L1/1966—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof poly-carboxylic
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  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/234—Macromolecular compounds
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
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  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/234—Macromolecular compounds
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2366—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amine groups
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  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
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  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/16—Hydrocarbons
  • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
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  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/234—Macromolecular compounds
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/234—Macromolecular compounds
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2368—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing heterocyclic compounds containing nitrogen in the ring
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L2200/00—Components of fuel compositions
  • C10L2200/02—Inorganic or organic compounds containing atoms other than C, H or O, e.g. organic compounds containing heteroatoms or metal organic complexes
  • C10L2200/0259—Nitrogen containing compounds
• • C—CHEMISTRY; METALLURGY
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  • C10L2200/00—Components of fuel compositions
  • C10L2200/04—Organic compounds
  • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
  • C10L2200/0438—Middle or heavy distillates, heating oil, gasoil, marine fuels, residua
• • C—CHEMISTRY; METALLURGY
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  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L2200/00—Components of fuel compositions
  • C10L2200/04—Organic compounds
  • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
  • C10L2200/0438—Middle or heavy distillates, heating oil, gasoil, marine fuels, residua
  • C10L2200/0446—Diesel
• • C—CHEMISTRY; METALLURGY
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  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L2200/00—Components of fuel compositions
  • C10L2200/04—Organic compounds
  • C10L2200/0461—Fractions defined by their origin
  • C10L2200/0469—Renewables or materials of biological origin
• • C—CHEMISTRY; METALLURGY
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  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L2200/00—Components of fuel compositions
  • C10L2200/04—Organic compounds
  • C10L2200/0461—Fractions defined by their origin
  • C10L2200/0469—Renewables or materials of biological origin
  • C10L2200/0476—Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
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  • C10L2250/00—Structural features of fuel components or fuel compositions, either in solid, liquid or gaseous state
  • C10L2250/04—Additive or component is a polymer
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
  • Y02E50/00—Technologies for the production of fuel of non-fossil origin
  • Y02E50/10—Biofuels, e.g. bio-diesel

Definitions

• the present invention relates to the use of polyalkyl(meth)acrylates as an additive to fuels, especially middle distillate fuels and blends thereof.
• the present invention further relates to the use of a composition comprising polyalkyl(meth)acrylates as dispersing species susceptible to disperse waxes and sludgy material at low temperatures and a hydrocarbon solvent or an oil for improving the cold flow properties of fuel oil and fuel oil compositions.
• the present invention further relates to the use of these compositions as an additive to fuels, especially in the function of paraffin dispersant, to such fuels themselves and to fuel additive concentrates which comprise this composition dissolved in a hydrocarbon solvent or an oil.
• biodiesel is in many cases understood to mean a mixture of fatty acid esters, usually fatty acid methyl esters (FAMEs), with chain lengths of the fatty acid fraction of 14 to 24 carbon atoms with 0 to 3 double bonds. The higher the carbon number and the fewer double bonds are present, the higher is the melting point of the FAME.
• Typical raw materials are vegetable oils (i.e. glycerides) such as rapeseed oils, sunflower oils, soya oils, palm oils, coconut oils and, in isolated cases, even used vegetable oils. These are converted to the corresponding FAMEs by transesterification, usually with methanol under basic catalysis.
• the FAME content also affects the cold flow properties of the feedstock.
• the common methods to evaluate the cold flow quality are: pour point (PP) test as mentioned in ASTM D97, filterability limit via cold filter plugging point (CFPP) test measured to DIN EN 1 16 or ASTM D6371 , and cloud point (CP) test as described in ASTM D2500.
• pour point (PP) test as mentioned in ASTM D97
• CFPP filterability limit via cold filter plugging point
• CP cloud point
• suitable additives can modify the crystal growth of the n-paraffins in middle distillate fuels.
• Very effective additives prevent middle distillate fuels from becoming solid even at temperatures a few degrees Celsius below the temperature at which the first paraffin crystals crystallize out. Instead, fine, readily crystallizing, separate paraffin crystals are formed which pass through filters in motor vehicles and heating systems or at least form a filter cake which is permeable to the liquid portion of the middle distillates, so that disruption-free operation is ensured.
• the effectiveness of the cold flow improvers is expressed in accordance to European Standard EN 1 16 indirectly by measuring the cold filter plugging point (CFPP).
• Ethylene-vinyl carboxylate copolymers have been used for some time as cold flow improvers (CFI) or middle distillate flow improvers (MDFI).
• CFI cold flow improvers
• MDFI middle distillate flow improvers
• One disadvantage of these additives is that the precipitated paraffin crystals, owing to their higher density compared to the liquid portion, tend to settle out more and more at the bottom of the vessel in the course of storage. As a result, a homogenous low-paraffin phase forms in the upper part of the vessel and a biphasic paraffin-rich layer at the bottom.
• MDFI middle distillate cold flow improvers
• BDFI biodiesel flow improvers
• WASA wax anti-settling agents
• US Patent No. 4,400,2708 discloses the efficiency of single molecules based on dialkyl amine derivatives of phthalic acid (PA derivatives).
• PA derivatives dialkyl amine derivatives of phthalic acid
• EP Patent No. 1 935 968 describes suitable wax anti-settling agents to be oil-soluble polar nitrogen of which substituents may be in the form of cations.
• the WASA are condensates of carboxylic acids or their anhydrides with primary or secondary amines containing at least one straight chain C 8- 4o alkyl segment.
• the preferred compound is the amide-amine salt formed by reacting 1 molar portion of phthalic anhydride with 2 molar portions of di-(hydrogenated tallow) amine.
• WO International Publication No. 2007/147753 a blend of 2 to 3 components is used to stabilize wax crystals in fuels and mixes thereof with biofuels (from B0.1 to B75).
• the blend consists of 5% to 95% by weight of polar molecule (which is not one of following), 1 to 50% by weight of an amid molecule made from the condensation of a polyamine structure (having 2 to 1000 N-atoms) and with C 8- 3o fatty acids, and which may be mixed with 0 to 50% by weight of a condensate of ⁇ , ⁇ -dicarboxylic acid (having 4 to 300 C-atoms) and primary amine.
• EDTA ethylenediaminotetraacetic acid
• ditallow amine 50 mol% blended with a condensate of diethylene triamine and oleic acid (37.5 mol%) and a condensate of maleic acid anhydride with tridecylamine (12.5 mol%).
• EP Patent No. 1 451 271 describes the use of oil soluble nitrogen compounds obtained by reaction of aliphatic or aromatic amines with aliphatic or aromatic mono, di-, tri-, or tetracarboxylic acids or their anhydrides.
• WASA chemistries are cited as part of the WAFI formulation (wax antisettling and flow improver).
• One of the chemistry is based on alkenyl-spirolactone reacted with secondary fatty amines having 8 to 36 carbon atoms.
• Example is given by dodecenyl-spirobislactone condensed with primary and secondary tallow amines.
• the second chemistry is provided by a terpolymer of vinyl monomers statistically copolymerized with allyl polyglycol ether and maleic acid anhydride and condensated with primary amines and/or aliphatic alcohol.
• a terpolymer of Ci 4 /Ci 6 -a-olefin, maleic anhydride and allylpolyglycol reacted with 2 moles of ditallow amines is mentioned as useful wax stabilizer.
• WASA a PAMA- based polymeric material having amino functionalities (e.g. for monomers
• DMAEMA dimethylaminoethylmethacrylate
• DMAEMA dimethylpropylmethacrylamide
• polyalkyl(meth)acrylate comprising monomer units of:
• R is H or CH 3 ,
• R 1 represents a linear or branched, saturated or unsaturated alkyl group with 1 to 9 carbon atoms or a cycloalkyl group with 3 to 9 carbon atoms,
• R 2 and R 3 independently represent H or a group of the formula -COOR', wherein R' is H or a linear or branched, saturated or unsaturated alkyl group with 1 to 9 carbon atoms or a cycloalkyl group with 3 to 9 carbon atoms, (b) 20% to 98% by weight of one or more ethylenically unsaturated ester compounds of formula (II)
• R is H or CH 3 ,
• R 4 represents a linear or branched, saturated or unsaturated alkyl group with 10 to 22 carbon atoms
• R 5 and R 6 independently represent H or a group of the formula -COOR", wherein R" is H or a linear or branched, saturated or unsaturated alkyl group with 10 to 22 carbon atoms, (c) 0% to 10% by weight of one or more ethylenically unsaturated ester compounds of formula (III)
• R is H or CHs
• R 7 represents a linear or branched, saturated or unsaturated alkyl group with 23 to 40 carbon atoms
• R 8 and R 9 independently represent H or a group of the formula -COOR'" wherein R'" is H or a linear or branched, saturated or unsaturated alkyl group with 23 to 40 carbon atoms,
• alkyi (meth)acrylate refers to both the alkyi acrylate and the alkyi methacrylate species or a mixture thereof. Alkyi methacrylates are preferred.
• component (a) include (meth)acrylates, fumarates and maleates which derive from saturated alcohols such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, tert-butyl
• (meth)acrylate pentyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate and nonyl (meth)acrylate; cycloalkyl
• (meth)acrylates like cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate and
• Monomer (a) is present in an amount of 0% to 40% by weight, preferably 0% to 20% by weight based on the total weight of components (a), (b), (c), (d) and (e).
• the amount of monomer (a) is at least 0.1 % by weight, preferably at least 0.5% by weight.
• the amount of monomer (a) is 0%.
• component (b) include (meth)acrylates, fumarates and maleates that derive from saturated alcohols, such as 2-tert-butylheptyl (meth)acrylate,
• unsaturated alcohols such as oleyl (meth)acrylate; cycloalkyi (meth)acrylates such as bornyl (meth)acrylate, 2,4,5-tri-tert-butyl-3-vinylcyclohexyl (meth)acrylate,
• Monomer (b) is present in an amount of 20% to 98% by weight, preferably 50% to 95% by weight, more preferably 70% to 90% by weight based on the total weight of components (a), (b), (c), (d) and (e).
• monomer (b) is a C 8- i5-alkyl (meth)acrylate, preferably
• the backbone monomer is a C 8- i5-alkyl methacrylate, preferably commercial lauryl methacrylate or a Ci 0 -i5-alkyl methacrylate fraction.
• component (c) include (meth)acrylates that derive from saturated alcohols, such as cetyleicosyl (meth)acrylate, stearyleicosyl (meth)acrylate and/or eicosyltetratriacontyl (meth)acrylate; as well as the corresponding fumarates and maleates.
• saturated alcohols such as cetyleicosyl (meth)acrylate, stearyleicosyl (meth)acrylate and/or eicosyltetratriacontyl (meth)acrylate.
• aromatic groups denote radicals of monocyclic or polycyclic aromatic compounds having preferably 6 to 20, more particularly 6 to 12, C atoms, such as, for example, phenyl, naphthyl or biphenylyl, preferably phenyl.
• Heteroaromatic groups identify aryl radicals in which at least one CH group is replaced by N and/or at least two adjacent CH groups are replaced by S, NH or O.
• radicals include, among others, groups derived from thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1 ,3,4-oxadiazole, 1 ,3,4-thiadiazole, 1 ,3,4-triazole, 1 ,2,4-oxa- diazole, 1 ,2,4-thiadiazole, 1 ,2,4-triazole, 1 ,2,3-triazole, 1 ,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole,
• benzothiadiazole benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1 ,3,5-triazine, 1 ,2,4-triazine, 1 ,2,4,5-triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1 ,8-naphthyridine, 1 ,5-naphthyridine, 1 ,6-naphthyridine, 1 ,1 '-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine or 4H-quinolizine.
• the preferred alkyl groups include the methyl, ethyl, propyl, isopropyl, 1 -butyl, 2-butyl, 2-methylpropyl, tert-butyl, pentyl, 2-methylbutyl, 1 ,1 -dimethylpropyl, hexyl, heptyl, octyl, 1 ,1 ,3,3-tetramethylbutyl, nonyl, 1 -decyl, 2-decyl, undecyl, dodecyl, pentadecyl and the eicosyl group.
• the preferred cycloalkyl groups include the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and the cyclooctyl group, which are unsubstituted or substituted by branched or non-branched alkyl groups.
• the preferred alkenyl groups include the vinyl, allyl, 2-methyl-2-propene, 2-butenyl,
• Monomer (c) is present in an amount of 0% to 10% by weight based on the total weight of components (a), (b), (c), (d) and (e).
• the amount of monomer (c) is at least 0.1 % by weight, preferably at least 0.5% by weight.
• Monomer (d) when present may be a vinyl aromatic monomer such as styrene and substituted styrenes although other vinyl monomers can also be used.
• the substituted styrenes include styrenes which are substituted with one or more substituents selected from the group consisting of halogen, amino, alkoxy with 1 to 12 carbon atoms in the alkyl residue, carboxy, hydroxy, sulfonyl, hydrocarbyl with 1 to 12 carbon atoms and other substituents.
• hydrocarbyl-substituted styrenes are alpha-methylstyrene, para-tert- butylstyrene, alpha-ethylstyrene, and para-lower alkoxy styrene having 1 to 12 carbon atoms. Mixtures of two or more vinyl monomers can be used. Styrene is preferred.
• the amount of vinyl monomer used is from 0% to 30% by weight, and when present, preferably from 5% to 25% by weight, more preferably 10% to 20% by weight, based on the total weight of components (a), (b), (c), (d) and (e).
• Monomer (e) is at least one monomer selected from the group consisting of N-vinylic monomers, (meth)acrylic esters, (meth)acrylic amides and (meth)acrylic imides each with dispersing moieties in the side chain and may be an N-dispersant monomer of the formula
• R 10 , R 11 and R 12 independently are H or a linear or branched, saturated or unsaturated alkyl group with 1 to 5 carbon atoms and R 13 is either a group selected from -C(0)-0-R 14 , -C(0)-NH-R 14 , -C(NR 15 )-0-R 14 ,
• R 15 represents a linear or branched, saturated or unsaturated alkyl group with 1 to 5 carbon atoms or an aryl group and
• R 14 represents a linear or branched alkyl group with 1 to 20 carbon atoms which is unsubstituted or substituted by a group -NR 16 R 17 , wherein R 16 and R 17 independently represent H or a linear or branched alkyl group with 1 to 8 carbon atoms, or wherein R 16 and R 17 are part of a 4- to 8-membered saturated or unsaturated ring containing optionally one or more hetero atoms chosen from the group consisting of nitrogen, oxygen or sulphur, wherein said ring may be further substituted with alkyl or aryl groups, and x represents a number 1 , 2, 3 or 4, or
• R 13 is a group -NR 18 R 19 , wherein R 18 and R 19 are part of a 4- to 8-membered saturated or unsaturated ring, containing at least one carbon atom as part of the ring which forms a double bond to a hetero atom chosen from the group consisting of nitrogen, oxygen or sulphur, wherein said ring may be further substituted with alkyl or aryl groups.
• R 14 represents H or a linear or branched alkyl group with 2 to 6 carbon atoms.
• N-dispersant monomers include those selected from the group consisting of vinyl substituted nitrogen heterocyclic monomers, for example vinyl pyridine and N-vinyl-substituted nitrogen heterocyclic monomers, for example, N-vinyl imidazole, N-vinyl pyrrolidinone (NVP), morpholinoethyl methacrylate and N-vinyl caprolactam,
• dialkylaminoalkyl acrylate and methacrylate monomers for example N,N-dialkylaminoalkyl (meth)acrylates, for example N,N-dimethylaminoethyl methacrylate (DMAEMA), tert-butyl aminoethyl methacrylate, dialkylaminoalkyl acrylamide and methacrylamide monomers, for example di-lower alkylaminoalkylacrylamide, especially where each alkyl or aminoalkyi group contains from 1 to 8 carbon atoms, especially from 1 to 3 carbon atoms, for example N,N-di lower alkyl, especially, N,N-dimethylaminopropylmethacrylamide (DMAPMAm),
• N-dispersant monomer may comprise a combination of
• R 10 , R 11 and R 12 are independently H or a linear or branched, saturated or unsaturated alkyl group with 1 to 5 carbon atoms and
• R is a group selected from -C(0)-0-R 14 , -C(0)-NH-R 14 , -C(NR 15 )-0-R '
• R 15 is an alkyl or aryl group and R 14 represents a linear or branched alkyl group with 1 to 20 carbon atoms which is unsubstituted or substituted by a group -NR 16 R 17 wherein R 16 and R 17 independently represent H or a linear or branched alkyl group with 1 to 8 carbon atoms, or wherein R 16 and R 17 are part of a 4 to 8 membered saturated or unsaturated ring containing optionally one or more hetero atoms chosen from the group consisting of nitrogen, oxygen or sulphur, wherein said ring may be further substituted with alkyl or aryl groups, and x represents a number 1 , 2, 3 or 4, and an N-dispersant monomer of the formula (IV)
• R 10 , R 11 and R 12 independently are H or an alkyl group with 1 to 5 carbon atoms and R 13 is a group -NR 18 R 19 , wherein R 18 and R 19 are part of a 4- to 8-membered saturated or unsaturated ring, containing at least one carbon atom as part of the ring which forms a double bond to a hetero atom chosen from the group consisting of nitrogen, oxygen or sulphur, wherein said ring may be further substituted with alkyl or aryl groups.
• the N-dispersant monomer may specifically be at least one monomer selected from the group consisting of N-vinyl pyrrolidinone, N,N-dimethylaminoethyl methacrylate and N,N- dimethylaminopropylmethacrylamide or a mixture thereof.
• the amount of N-dispersant monomer is typically from 2% to 80%, preferably from 5% to 50% by weight, and even more preferably from 10% to 30% by weight, based on the total weight of components (a), (b), (c), (d) and (e).
• the polyalkyl(meth)acrylate typically have a number average molecular weight M n of from 1000 to 1000000 g/mol, preferably 2000 to 100000 g/mol, more preferably 2500 to 100000 g/mol, even more preferably 2500 to 50000 g/mol and especially preferred 4000 to 20000 g/mol as measured by size exclusion chromatography, calibrated versus a polystyrene standard.
• the polydispersity M w /M n of the polyalkyl(meth)acrylate polymers preferably is in the range of from 1 to 8, especially from 1 .05 to 6.0, more preferably from 1 .1 to 5.0 and most preferably from 1 .3 to 2.5.
• the weight average molecular weight M w , the number average molecular weight M n and the polydispersity M w /M n can be determined by GPC using a methyl methacrylate polymer as standard.
• polyalkyl(meth)acrylate comprising monomer units of:
• R is H or CHs
• R 4 represents a linear or branched, saturated or unsaturated alkyl group with 10 to 22 carbon atoms
• R 5 and R 6 independently represent H or a group of the formula -COOR", wherein R" is H or a linear or branched, saturated or unsaturated alkyl group with 10 to 22 carbon atoms,
• R is H or CH 3 ,
• R 7 represents a linear or branched, saturated or unsaturated alkyl group with 23 to 40 carbon atoms
• R 8 and R 9 independently represent H or a group of the formula -COOR'" wherein R'" is H or a linear or branched, saturated or unsaturated alkyl group with 23 to 40 carbon atoms, (c) 0% to 30% by weight of vinyl aromatic monomers, and
• polyalkyl(meth)acrylate polymers are not critical for many applications and properties. Accordingly, these polymers may be random copolymers, gradient copolymers, block copolymers and/or graft copolymers. Block copolymers and gradient copolymers can be obtained, for example, by altering the monomer composition
• the polymers are preferably random copolymers.
• the combination according to the present invention is suitable as an additive to fuels, especially middle distillate fuels.
• Middle distillate fuels are often referred to as fuels oils. They find use in particular in gas oils, petroleum, diesel oils or diesel fuels or light and extra light heating oils and have generally boiling points from 150°C to 400°C.
• a further embodiment of the present invention comprises the use of a concentrate, comprising:
• R is H or CHs
• R 1 represents a linear or branched, saturated or unsaturated alkyl group with 1 to 9 carbon atoms or a cycloalkyl group with 3 to 9 carbon atoms,
• R 2 and R 3 independently represent H or a group of the formula -COOR', wherein R' is H or a linear or branched, saturated or unsaturated alkyl group with 1 to 9 carbon atoms or a cycloalkyl group with 3 to 9 carbon atoms,
• R is H or CHs
• R 4 represents a linear or branched, saturated or unsaturated alkyl group with 10 to 22 carbon atoms
• R 5 and R 6 independently represent H or a group of the formula -COOR", wherein R" is H or a linear or branched, saturated or unsaturated alkyl group with 10 to 22 carbon atoms,
• R is H or CHs
• R 7 represents a linear or branched, saturated or unsaturated alkyl group with 23 to 40 carbon atoms
• R 8 and R 9 independently represent H or a group of the formula -COOR'" wherein R'" is H or a linear or branched, saturated or unsaturated alkyl group with 23 to 40 carbon atoms,
• hydrocarbon solvents in this context are aliphatic or aromatic hydrocarbons such as xylenes or mixtures of high-boiling aromatics as for example Solvent Naphtha.
• Middle distillate fuels themselves may also be used as the solvent for such concentrates.
• the concentrate may comprise from 10% to 70% by weight, preferably from 30% to 65% by weight, and more preferred from 45% to 60% by weight, based on the total amount of the concentrate, of the inventive polyalkyl(meth(acrylate) as described above.
• the inventive concentrate is used as an additive to fuels which consists of
• the fuel component (i) shall be understood to mean middle distillate fuels boiling in the range of from 120°C to 450°C. Such middle distillate fuels are used in particular as diesel fuel, heating oil or kerosene. Preference is given to diesel fuel and heating oil.
• the fuel composition of the present invention may comprise diesel fuel of mineral origin, i.e. diesel, gas oil or diesel oil.
• Mineral diesel fuel is widely known per se and is commercially available. This is understood to mean a mixture of different hydrocarbons which is suitable as a fuel for a diesel engine. Diesel can be obtained as a middle distillate, in particular by distillation of crude oil.
• the main constituents of the diesel fuel preferably include alkanes, cycloalkanes and aromatic hydrocarbons having about 10 to 22 carbon atoms per molecule.
• Preferred diesel fuels of mineral origin boil in the range of 120°C to 450°C, more preferably 170°C and 390°C.
• They are preferably those middle distillates which have been subjected to refining under hydrogenating conditions, and which therefore contain only small proportions of polyaromatic and polar compounds.
• Synthetic fuels are preferably those middle distillates which have 95% distillation points below 370°C, in particular below 350°C and in special cases below 330°C.
• Synthetic fuels as obtainable, for example, by the Fischer-Tropsch process or gas to liquid processes (GTL), are also suitable as diesel fuels of mineral origin.
• the kinematic viscosity of diesel fuels of mineral origin to be used with preference is in the range of 0.5 to 8 mm 2 /s, more preferably 1 to 5 mm 2 /s, and especially preferably 2 to 4.5 mm 2 /s or 1 .5 to 3 mm 2 /s, measured at 40°C to ASTM D 445.
• the fuel compositions of the present invention may comprise at least 20% by weight, in particular at least 30% by weight, preferably at least 50% by weight, more preferably at least 70% by weight and most preferably at least 80% by weight of diesel fuels of mineral origin.
• the present fuel composition may comprise at least one biodiesel fuel component.
• Biodiesel fuel is a substance, especially an oil, which is obtained from vegetable or animal material or both, or a derivative thereof which can be used in principle as a replacement for mineral diesel fuel.
• biodiesel fuel which is frequently also referred to as
• biodiesel or “biofuel” comprises fatty acid alkyl esters formed from fatty acids having preferably 6 to 30, more preferably 12 to 24 carbon atoms, and monohydric alcohols having 1 to 4 carbon atoms. In many cases, some of the fatty acids may contain one, two or three double bonds.
• the monohydric alcohols include in particular methanol, ethanol, propanol and butanol, methanol being preferred.
• oils which derive from animal or vegetable material and which can be used in accordance with the invention are palm oil, rapeseed oil, coriander oil, soya oil, cottonseed oil, sunflower oil, castor oil, olive oil, groundnut oil, corn oil, almond oil, palm kernel oil, coconut oil, mustard seed oil, oils which are derived from animal tallow, especially beef tallow, bone oil, fish oils and used cooking oils.
• oils which derive from cereal, wheat, jute, sesame, rice husks, jatropha, algae, arachis oil and linseed oil may be obtained from these oils by processes known in the prior art.
• Palm oil also: palm fat
• the oil may contain up to 80% C18:0- glyceride.
• biodiesel fuels are lower alkyl esters of fatty acids.
• Useful examples here are commercial mixtures of the ethyl, propyl, butyl and especially methyl esters of fatty acids having 6 to 30, preferably 12 to 24, more preferably 14 to 22 carbon atoms, for example of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, arachic acid, behenic acid, lignoceric acid, cerotic acid, palmitoleic acid, stearic acid, oleic acid, elaidic acid, petroselic acid, ricinoleic acid, elaeostearic acid, linoleic acid, linolenic acid, eicosanoic acid, gadoleic acid, docosanoic acid or erucic acid.
• a biodiesel fuel which comprises preferably at least 10% by weight, more preferably at least 30% by weight and most preferably at least 40% by weight of saturated fatty acid esters which are derived from methanol and/or ethanol.
• these esters have at least 16 carbon atoms in the fatty acid part. These include in particular the esters of palmitic acid and stearic acid.
• the inventive fuel composition may comprise further additives in order to achieve specific solutions to problems.
• additives include other cold flow improvers different than those described above, dispersants, for example wax dispersants and dispersants for polar substances, conductivity improvers, demulsifiers, defoamers, lubricity additives, additional antioxidants, cetane number improvers, detergents, dyes, corrosion inhibitors, metal deactivators, metal passivators and/or odourants.
• a further object of the present invention is directed to a method for improving the cold flow properties of fuel oil compositions, comprising the steps of adding at least one
• a further object of the present invention is directed to a method for improving the cold flow properties of fuel oil compositions, comprising the steps of:
• the monomer mixtures described above can be polymerized by methods known in the art.
• the copolymers of this invention may be prepared by processes comprising reacting monomers (a) to (e) in the presence of a free radical initiator and optionally in the presence of a chain transfer agent. The monomers may be reacted concurrently.
• radical initiators can be used to perform a classic radical polymerization. These initiators are well known in the art. Examples for these radical initiators are azo initiators like 2,2'-azodiisobutyronitrile (AIBN), 2,2'-azobis(2-methylbutyronitrile) and
• peroxide compounds e.g. methyl ethyl ketone peroxide, acetyl acetone peroxide, dilauryl peroxide, tert-butyl per-2-ethyl hexanoate, ketone peroxide, methyl isobutyl ketone peroxide, cyclohexanone peroxide, dibenzoyl peroxide, tert-butyl perbenzoate, tert-butyl peroxy isopropyl carbonate, 2,5-bis(2-ethylhexanoyl-peroxy)- 2,5-dimethyl hexane, tert-butyl peroxy 2-ethyl hexanoate, tert-butyl peroxy-3,5,5-trimethyl hexanoate, dicumene peroxide, 1 ,1 -bis(tert-butyl peroxy
• Chain transfer agents Low molecular weight poly(meth)acrylates can be obtained by using chain transfer agents. This technology is ubiquitously known and practiced in the polymer industry and is described in Odian, Principles of Polymerization, 1991.
• chain transfer agents are aldehydes or sulphur containing compounds such as thiols, e.g. n- and tert-dodecanethiol, 2-mercaptoethanol, and mercapto carboxylic acid esters, e.g. methyl-3-mercaptopropionate.
• Preferred chain transfer agents contain up to 20, especially up to 15 and more preferably up to 12 carbon atoms.
• chain transfer agents may contain at least 1 , especially at least 2 oxygen atoms.
• ATRP Atom Transfer Radical Polymerization
• RAFT Reversible Addition Fragmentation Chain Transfer
• ATRP reaction method is described, for example, by J.-S. Wang, et al., J. Am. Chem. Soc, Vol. 1 17, pp. 5614-5615 (1995), and by Matyjaszewski, Macromolecules, Vol. 28, pp. 7901 -7910 (1995).
• the patent applications WO 96/30421 , WO 97/47661 , WO 97/18247, WO 98/40415 and WO 99/10387 disclose variations of the ATRP explained above to which reference is expressly made for purposes of the disclosure.
• the RAFT method is extensively presented in WO 98/01478, for example, to which reference is expressly made for purposes of the disclosure.
• the polymerization can be carried out at normal pressure, reduced pressure or elevated pressure.
• the polymerization temperature is also not critical. However, in general it lies in the range of -20°C to 200°C, preferably 0°C to 130°C and especially preferably 60°C to 120°C, without any limitation intended by this.
• the polymerization can be carried out with or without solvents.
• solvent is to be broadly understood here.
• the polymerization is carried out in a nonpolar solvent.
• solvents such as hydrocarbon solvents, such as aromatic solvents like toluene, benzene and xylene, saturated hydrocarbons such as cyclohexane, heptane, octane, nonane, decane, dodecane, which can also occur in branched form.
• solvents can be used individually and as a mixture.
• Especially preferred solvents are mineral oils and synthetic oils and mixtures of these. Of these, mineral oils are most preferred. Mineral oils are substantially known and commercially available.
• mineral oils are generally obtained from petroleum or crude oil by distillation and/or refining and optionally additional purification and processing methods, especially the higher-boiling fractions of crude oil or petroleum fall under the concept of mineral oil.
• the boiling point of the mineral oil is higher than 200°C, preferably higher than 300°C, at 50 mbar.
• Preparation by low temperature distillation of shale oil, coking of hard coal, distillation of lignite under exclusion of air as well as hydrogenation of hard coal or lignite is likewise possible.
• mineral oils are also produced from raw materials of plant origin (for example jojoba, rapeseed oil) or animal origin (for example neatsfoot oil). Accordingly, mineral oils exhibit different amounts of aromatic, cyclic, branched and linear hydrocarbons in each case, according to origin.
• Natural oils include animal oils and vegetable oils (e.g., castor oil, lard oil); liquid petroleum oils and hydro-refined, solvent-treated or acid-treated mineral oils of the paraffinic, naphthenic and mixed paraffinic-naphthenic types.
• solvents can be used, among other ways, in an amount of 1 % to 99% by weight, preferably 5% to 95% weight, especially preferably 5% to 60% by weight and most preferably 10% to 50% by weight, with respect to the total weight of the mixture, without any limitation intended to be implied by this.
• the process comprises reacting a mixture of the monomers, often by first heating a portion, often from about 20% to about 60%, of the mixture until reaction is evident, usually by noting an exotherm, then adding and reacting the balance of the mixture of monomers, either portion wise, or all at once.
• ethylenediaminotetraacetic acid EDTA
• PA phthalic anhydride
• Alpha-olefin ethylenediaminotetraacetic acid
• WASA ethylenediaminotetraacetic acid
• M n of the polymer is around 5000 g/mol
• M w of the polymer is around 9000 g/mol. If there is any exception in the molecular weight, then WASA are noted with M .
• Component A EDTA condensed with 4 moles of di-tallow amine in solvent Naphta;
• Component C Alpha-olefin-stat-MA condensed with di-tallow amine in solvent Naphta;
• Component D dodecyl/pentadecyl methacrylate
• Component E dodecyl/pentadecyl methacrylate-stat-2- dimethylaminoethylmethacrylate (70/30 wt%);
• Component F dodecyl/pentadecyl methacrylate-stat-2- dimethylaminoethylmethacrylate (85/15 wt%);
• Component G lauryl methacrylate/stearyl methacrylate-stat- dimethylaminoethylmethacrylate (70/30 wt%);
• Component H dodecyl/pentadecyl methacrylate-stat- dimethylaminopropylmethacrylamide (70/30 wt%);
• Table 1 compositions tested as WASA. Values given in wt%.
• W1 to W4 represent comparative examples and W5 to W8 represent examples of the
• Component A is a compound having Component A:
• Component B is a compound having Component B:
• the handling properties i.e. temperature limits for handling of the different WASA have been compared by determining cloud and pour points (according to ASTM D97 and D2500
• Table 2 Cold flow properties of the WASA 70% in Shellsol A 150 ND.
• 500 mL glassware containing the fuel blended with the additives to be tested 250 ppm of EVA-based MDFI and 150 ppm of WASA) is plunged in an ethanol bath. Before sedimentation, CP, CFPP and PP of the sample are measured.
• the ethanol bath is cooled down to a certain temperature depending on the CP and PP of the fuel + additives as the sample should not freeze (temperature well above PP and below CP). Cooling rate is of 0.24°C/min and the sample is let at temperature 16 hours long. After this period of time, 80% of the upper volume contained in the glassware, the upper phase, is carefully removed and with the remaining 20%, the bottom phase, CP was determined after homogenization.
• ACP describes the difference between CP "20% remaining" and CP "initial". The smaller the ACP is the more efficient the wax anti-settling agent is. In general it is expected that a good WASA provides ACP of 2°C or below. Table 3: ACP of B0 and B10 DK1 treated with WASA comparative examples (W1 and
• W3 and invention products W5-8.
• WASA with * have M n around 24000 g/mol.
• W5 to W8 show similar performances in B0 DK1 as the comparative examples. Moreover W8 even shows better efficiency than W1 -3. Even higher molecular weight WASAs, W5* and W8* (M n around 24000 g/mol), show very good anti-settling performance.
• the WASA of the invention display same
• WASA alpha-olefin-based
• WASA comparative examples W1 to W4
• invention products W5 to W8
• WASA component with * have M n around 24000 g/mol.
• Table 4 are displayed the ACP values obtained during the sedimentation tests in fuel DK2 and blend thereof with 10% RME.
• products of the invention show ACP values between 2.2°C and 2.8°C which is comparable to the performance obtained using comparative examples W2 and W3 with 2.3°C and 3.7°C respectively.
• W8 provides the best wax stabilization as ACP of 1.4°C was measured.
• W1 to W4 show very poor efficiency without exceptions. It is interesting to notice that the reference WASA W4 differs from the inventive examples as it does not possess N- dispersant functionality. On the contrary, inventive WASA W7, W8 and W8* display much better ACP values of 1.2 and 1.0°C for number molecular weight of 5000 g/mol and of 2.3°C for 24000 g/mol.
• Table 5 ACP of B0 and B10 DK3 treated with WASA comparative examples (W1 , W3 and W4) and invention products (W5 to W8).
• WASA component with * have M n around 24000 g/mol Fuel type EVA MDFI WASA type ACP

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