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  • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
  • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
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  • 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
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  • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
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  • C10L10/00—Use of additives to fuels or fires for particular purposes
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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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  • C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
  • C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
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  • C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
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  • C10L1/234—Macromolecular compounds
  • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
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  • C10L2200/00—Components of fuel compositions
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  • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
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  • C10L2200/0461—Fractions defined by their origin
  • C10L2200/0469—Renewables or materials of biological origin
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  • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
  • C10L2230/14—Function and purpose of a components of a fuel or the composition as a whole for improving storage or transport of the fuel

Definitions

• the present invention relates to polyalkyl (meth)acrylates (PAMAs) containing dispersant repeating units and their use as an additive component to fuels, especially to middle distillates and blends thereof.
• PAMAs polyalkyl (meth)acrylates
• the present invention further relates to a composition comprising polyalkyl (meth)acrylates containing dispersant repeating units as dispersing species and the use of said composition as an additive to fuels, especially to middle distillates and blends thereof, and for improving the cold flow properties of fuel oil and fuel oil compositions, especially to middle distillate fuels and blends thereof.
• middle distillate fuels typified by diesel oil , heating oil, jet fuel, fuel oils, kerosene etc. may be stored for extended periods of time under unfavourable conditions which are conducive to formation of solid deposits.
• insoluble sediments results e.g. in decreased filter flow rates or increased nozzle plugging tendency.
• additives are added to the diesel fuels and heating oils in the mineral oil refineries, at fuel terminals or fuel blenders.
• Typical used multifunctional additive packages comprise antioxidants, detergent additives and optionally cetane improvers as the main constituents as well as cold flow improvers, static dissipator additives, metal deactivators and anti-icing additives.
• a grafted polyalkyl (meth)acrylate copolymer containing N- dispersant monomers both in the polymer backbone as well as in the grafted side-chain can be used to stabilize additive packages for middle distillates as a compatibilizer.
• the polymer can disperse particles, aged components like sludge and gum and/or n-paraffin wax crystals.
• the inventive polymers preferably have a nitrogen content of at least 1 % by weight, especially preferred 1 % to 7% by weight.
• inventive polymers allows formulating stable homogeneous fuel additive packages with multiple functions.
• the main purpose of the additive packages is to stabilize the fuel versus ageing and oxidation.
• the inventive polymer improves the stabilizer performance as determined in the "Thermal Stability Test" and helps to disperse particles.
• Fuel additive packages optionally allow improving low temperature properties and/or lubricity, conductivity, cetane number, corrosiveness, combustion and smell. Chemically very different components are not necessarily compatible without the inventive polymers.
• a dispersing additive is necessary to produce stable formulations and ensure storage stability without phase separation.
• Such N-dispersant polymers can be prepared by copolymerizing N-containing monomers.
• US Patent No. 6,051 ,039 describes the use of various poly-isobutylene succinimides and conversion products of long chain succinic acids with different amines and their use to improve the storage stability of diesel fuel according to ASTM D2274.
• the diesel fuel composition is claimed. It is also claimed that rust inhibition and lubricity is improved by this kind of additive.
• US patent application publication No. 2009/0307964 A1 describes the use of compatibilizers for multifunctional additive packages.
• the exemplary packages contain: 1 ) cold flow improver; 2) polyisobutylene succinimide as detergent; 3) solvent naphtha; 4) optionally 2- ethylhexylnitrate as cetane number improver; 5) optionally ethylene glycol monomethylether; and 6) compatibilizer.
• the compatibilizer can be obtained from the reaction of maleic acid or phthalic acid with amines.
• a wide range of non-polymeric molecules are claimed, which typically contain nitrogen and carboxylic groups.
• US Patent No. 5,035,719 describes the use of polyalkyi (meth)acrylates containing moieties derived from N-heterocyclic amines to improve the stability of middle distillates according to ASTM D2274. Sulphur containing lauryl mercaptane was used as chain transfer agent. A liquid middle distillate fuel containing a small portion of this kind of polymer is claimed. The use as compatibilizer in additive packages is not discussed.
• a grafted polyalkyl (meth)acrylate copolymer (A), containing as a polymer backbone monomer units comprising:
• R is H or CH 3 ,
• R 1 represents a linear or branched, saturated or unsaturated alkyl group with 1 to 5 carbon atoms or a cycloalkyl group with 3 to 5 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 5 carbon atoms or a cycloalkyl group with 3 to 5 carbon atoms,
• R is H or CHs
• R 4 represents a linear or branched, saturated or unsaturated alkyl group with 6 to 15 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 6 to 15 carbon atoms,
• R is H or CHs
• R 7 represents a linear or branched, saturated or unsaturated alkyl group with 16 to 30 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 16 to 30 carbon atoms, and
• N-dispersant monomer selected from the group consisting of vinyl pyridine, N-vinyl imidazole, N-vinyl pyrrolidone (NVP),
• N-dispersant monomer selected from the group consisting of vinyl pyridine, N-vinyl imidazole, N-vinyl pyrrolidone (NVP),
• alkyi (meth)acrylate refers to both the alkyi acrylate and the alkyi methacrylate species or a mixture thereof. Alkyi methacrylates are preferred.
• Non-limiting examples of component (A1 ) include acrylates, methacrylates, 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, ie f-butyl (meth)acrylate and pentyl (meth)acrylate; cycloalkyl (meth)acrylates, like cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate and 3-vinylcyclohexyl (meth)acrylate; (meth)acrylates that derive from unsaturated alcohols like 2-propynyl (meth)acrylate, allyl (meth)acrylate and vinyl (meth)acrylate; and the corresponding fumarates and maleates.
• Monomer (A1 ) is present in an amount of 0% to 40% by weight, preferably 1 % to 20% by weight, based on the total weight of components (A1 ), (A2), (A3) and (A4).
• component (A1 ) comprises monomer units of one or more ethylenically unsaturated ester compounds of formula (I)
• R is H or CH 3 , preferably CH 3 ,
• R 1 represents a linear or branched, saturated or unsaturated alkyi group with 1 to 5 carbon atoms or a cycloalkyl group with 3 to 5 carbon atoms and
• R 2 and R 3 independently represent H.
• component (A2) include (meth)acrylates, fumarates and maleates that derive from saturated alcohols, such as hexyl (meth)acrylate, 2-ethylhexyl
• (meth)acrylate 5-methyltridecyl (meth)acrylate, tetradecyl (meth)acrylate and pentadecyl (meth)acrylate; cycloalkyl (meth)acrylates such as bornyl (meth)acrylate, 2,4,5-tri-ie f-butyl-
• Monomer (A2) is present in an amount of 20% to 93.5% by weight, preferably 30% to 60% by weight, based on the total weight of components (A1 ), (A2), (A3) and (A4).
• monomer (A2) is a C 8- i5-alkyl (meth)acrylate, preferably commercial lauryl(meth)acrylate, or a Ci 0 -i5-alkyl (meth)acrylate fraction. More preferably the backbone monomer is a C 8- i5-alkyl methacrylate, preferably commercial lauryl methacrylate or a
• Cio-15-alkyl methacrylate fraction Cio-15-alkyl methacrylate fraction.
• component (A2) comprises monomer units of one or more ethylenically unsaturated ester compounds of formula (II) wherein
• R is H or CH 3 , preferably CH 3 ,
• R 4 represents a linear or branched, saturated or unsaturated alkyl group with 6 to 15 carbon atoms and
• R 5 and R 6 independently represent H.
• component (A3) include (meth)acrylates that derive from saturated alcohols, such as hexadecyl (meth)acrylate, 2-methylhexadecyl (meth)acrylate, heptadecyl (meth)acrylate, 5-isopropylheptadecyl (meth)acrylate, 4-ie f-butyloctadecyl (meth)acrylate, 5-ethyloctadecyl (meth)acrylate, 3-isopropyloctadecyl (meth)acrylate, octadecyl
• Monomer (A3) is present in an amount of 5% to 60% by weight, preferably 20% to 50% by weight, based on the total weight of components (A1 ), (A2), (A3) and (A4).
• component (A3) comprises monomer units of one or more ethylenically unsaturated ester compounds of formula (III)
• R is H or CH 3 , preferably CH 3 ,
• R 7 represents a linear or branched, saturated or unsaturated alkyl group with 16 to 30 carbon atoms
• R 8 and R 9 independently represent H.
• the N-dispersant monomer (A4) may specifically be at least one monomer selected from the group consisting of vinyl pyridine, N-vinyl imidazole, N-vinyl pyrrolidone (NVP),
• DMAEMA N,N-dimethylaminoethyl methacrylate
• DMAPMAm N,N-dimethylaminopropylmethacrylamide
• N-dispersant monomer (A4) is selected from the group consisting of N-vinyl pyrrolidone (NVP), ⁇ , ⁇ -dimethylaminoethyl methacrylate (DMAEMA) and N,N-dimethylaminopropylmethacrylamide (DMAPMAm); especially preferred is N-vinyl pyrrolidone.
• NRP N-vinyl pyrrolidone
• DMAEMA ⁇ , ⁇ -dimethylaminoethyl methacrylate
• DMAPMAm N,N-dimethylaminopropylmethacrylamide
• the amount of N-dispersant monomer (A4) is typically from 1 % to 40% by weight, preferably from 2% to 30% by weight, based on the total weight of components (A1 ), (A2), (A3) and (A4).
• the N-dispersant monomer (A5) which is grafted onto the polymer backbone, may specifically be at least one monomer selected from the group consisting of vinyl pyridine, N- vinyl imidazole, N-vinyl pyrrolidone (NVP), morpholinoethyl methacrylate, N-vinyl
• DMAEMA N,N-dimethylaminoethyl methacrylate
• DMAPMAm ie f-butyl aminoethyl methacrylate
• DMAPMAm ⁇ , ⁇ -dimethylaminopropylmethacrylamide
• N-dispersant monomer (A5) is selected from the group consisting of N-vinyl pyrrolidone (NVP), N,N-dimethylaminoethyl methacrylate (DMAEMA) and N,N-dimethylaminopropylmethacrylamide (DMAPMAm); especially preferred is N-vinyl pyrrolidone.
• NDP N-vinyl pyrrolidone
• DMAEMA N,N-dimethylaminoethyl methacrylate
• DMAPMAm N,N-dimethylaminopropylmethacrylamide
• the amount of N-dispersant monomer (A5) is typically from 0.5% to 10% by weight, preferably from 1 % to 7% by weight, based on the total weight of components (A1 ), (A2), (A3) and (A4).
• (meth)acrylate copolymer (A) wherein the overall nitrogen content is at least 1 % by weight, preferably 1 % to 7% by weight, based on the total content of components (A1 ) to (A5).
• the nitrogen is part of an aminic functionality.
• 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 optionally are substituted by branched or non- branched alkyl groups.
• the preferred alkenyl groups include the vinyl, allyl, 2-methyl-2-propene, 2-butenyl,
• the polyalkyl (meth)acrylates according to the present invention typically have a number average molecular weight M n of from 3000 to 150000, preferably 10000 to 100000, 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 1.5 to 5.0.
• 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 polystyrene as standard.
• the molecular weight and the polydispersity can be determined by known methods. For example, gel permeation chromatography (GPC) can be used. It is equally possible to use an osmometric process, for example vapor phase osmometry, to determine the molecular weights.
• GPC gel permeation chromatography
• osmometric process for example vapor phase osmometry
• the architecture of the polymer backbone of the polyalkyl(meth)acrylate polymers is not critical for many applications and properties. Accordingly, these polymers may be random copolymers, gradient copolymers, block copolymers, star polymers, hyperbranched polymers and/or graft copolymers. Block copolymers and gradient copolymers can be obtained, for example, by altering the monomer composition discontinuously during the chain growth. According to the present invention, random copolymers are prepared as polymer backbone.
• a second aspect of the present invention is directed to the use of the grafted
• polyalkyl(meth)acrylate copolymers as defined above as a compatibilizer for additive packages, especially for additive packages for middle-distillates.
• a third aspect of the present invention is directed to the use of the grafted
• polyalkyl(meth)acrylate copolymers as defined above as a component in additive packages to stabilize middle-distillates.
• a fourth aspect of the present invention is directed to the use of the grafted
• 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 addition is preferably done at temperatures well above the cloud point of the used fuels, preferably at least 10°C above the cloud point.
• a fifth aspect of the present invention is directed to the use of the grafted
• the polymer according to the present invention is suitable as an additive to fuels, especially middle distillate fuels, renewable fuels and mixtures thereof.
• Middle distillate fuels are often referred to as fuel oils. They find use in particular in gas oils, petroleum, kerosene, diesel oils or diesel fuels or light and extra light heating oils and have generally boiling ranges from minimum 150°C to maximum 400°C.
• the heating oils are, for example, low-sulfur or sulfur-rich crude oil raffinates or bituminous or brown coal distillates which typically have a boiling range of from 150 to 400°C.
• the heating oils may be standard heating oils according to DI N 51603-1 , which has a sulfur content of from 0.005 to 0.2% by weight, or they are low-sulfur heating oils having a sulfur content of from 0 to 0.005% by weight.
• Examples of heating oil include in particular heating oil for domestic oil-fired boilers or heating oil extra light (H EL).
• H EL heating oil extra light
• DI N V 51603-6 describes low-sulphur heating oils with max 0,005 w% Sulphur and biofuel fractions of up to 20w%, so called H EL A Bio.
• the diesel fuels are, for example, crude oil raffinates which typically have a boiling range from 100 to 400°C. They may also be so-called “Gas Oil”, “Diesel Fuel Oil”, “No.2 Diesel”, “ultra low sulfur diesel” or “city diesel”, characterized by a 95% point of, for example, not more than 360°C and a sulfur content of not more than 0.005% by weight, or by a 90% point of, for example, 282°C and a sulfur content of not more than 0.0015 % by weight. Diesel fuel specifications are, for example, ASTM D975 or DI N EN 590.
• suitable diesel fuels also include those obtainable by coal gasification or gas liquefaction ["gas-to-liquid"
• diesel fuels or by biomass liquefaction ["biomass-to-liquid” (“BTL”) fuels].
• renewable fuels such as biodiesel, vegetable oils, hydrotreated vegetable oils or bio-methyl ie f-butyl ether (MTBE).
• the diesel fuels are more preferably those having a low sulfur content, i.e. having a sulfur content of less than 0.05% by weight, preferably of less than 0.02% by weight, in particular of less than 0.005% by weight and especially of less than 0.0015 % by weight of sulfur.
• Biodiesel (also referred to as biofuel oil) preferably comprises essentially alkyl esters of fatty acids which derive from vegetable and/or animal oils and/or fats.
• Alkyl esters are understood to mean typically lower alkyl esters, especially Ci -4 - alkyl esters, which are obtainable by transesterifying the glycerides which occur in vegetable and/or animal oils and/or fats, especially triglycerides, by means of lower alcohols, for example ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, tert-butanol or especially methanol (“FAME": fatty acid methyl esters).
• FAME fatty acid methyl esters
• oils which are converted to corresponding alkyl esters and can thus serve as the basis for biodiesel are castor oil, olive oil, peanut oil, palm kernel oil, coconut oil, mustard oil, cottonseed oil and especially sunflower oil, palm oil, soybean oil, canola oil and rapeseed oil.
• animal fats and oils which are converted to corresponding alkyl esters and can thus serve as the basis for biodiesel are fish oil, bovine or beef tallow, porcine tallow and similar fats and oils obtained as wastes in the slaughter or utilization of farm animals or wild animals.
• the parent saturated or unsaturated fatty acids of the vegetable and/or animal oils and/or fats mentioned said fatty acids usually having from 12 to 22 carbon atoms and possibly bearing additional functional groups such as hydroxyl groups.
• Typical are lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, elaidic acid, erucic acid and ricinoleic acid, and especially mixtures of such fatty acids.
• Typical lower alkyl esters based on vegetable and/or animal oils and/or fats which find use as biodiesel or biodiesel components are, for example, sunflower methyl ester, palm oil methyl ester ("PME”), soybean oil methyl ester (“SME”) and especially rapeseed oil methyl ester (“RME”).
• PME palm oil methyl ester
• SME soybean oil methyl ester
• RME rapeseed oil methyl ester
• a sixth aspect of the present invention is directed to a composition, comprising:
• hydrocarbon solvent and an oil, wherein components (A) and (B) add up to 100% by weight.
• Common 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 or biofuels themselves may also be used as the solvent for such concentrates.
• composition may comprise from 10% to 90% by weight, preferably from 30% to 80% by weight, and more preferred from 45% to 75% by weight, based on the total amount of the concentrate, of the inventive polyalkyl(meth(acrylate) as described above.
• a seventh aspect of the present invention is directed to the use of the composition as defined above as a compatibilizer for additive packages, especially for additive packages for middle- distillates.
• An eighth aspect of the present invention is directed to the use of the composition as defined above as a component in additive packages to stabilize middle-distillates.
• a ninth aspect of the present invention is directed to the use of the composition as defined above for improving the cold flow properties of middle distillates.
• 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:
• a tenth aspect of the present invention is directed to the use of the composition as defined above for reducing n-Paraffin wax sedimentation in middle distillates, preferably in diesel fuels.
• the inventive concentrate is used as an additive to fuels which consists of
• the fuel component (a) shall be understood to mean middle distillate fuels boiling in the range of from 120°C to 400°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 400°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 360°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 according 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. Especially, 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 grafted polyalkyi (meth)acrylate copolymer according to the present invention and the composition comprising said grafted polyalkyi (meth)acrylate copolymer may be used in additive packages for middle distillates.
• Such additive packages comprise one or more additives selected from the group consisting of cold flow improvers, dispersants, conductivity improvers, demulsifiers, defoamers, lubricity additives, antioxidants, cetane number improvers, detergents, dyes, markers, corrosion inhibitors, metal deactivators, metal passivators, anti-icing additives, H 2 S-scavengers, biocides, odorants and/or other compatibilizers.
• additives selected from the group consisting of cold flow improvers, dispersants, conductivity improvers, demulsifiers, defoamers, lubricity additives, antioxidants, cetane number improvers, detergents, dyes, markers, corrosion inhibitors, metal deactivators, metal passivators, anti-icing additives, H 2 S-scavengers, biocides, odorants and/or other compatibilizers.
• a further aspect of the present invention is directed to a composition, comprising:
• a grafted polyalkyi (meth)acrylate copolymer according to the invention (i) a grafted polyalkyi (meth)acrylate copolymer according to the invention; (ii) an antioxidant, selected from the group consisting of phenolic antioxidants, for example butylated hydroxytoluene;
• a metal deactivator for example N,N-disalicylidene-1 ,2-propandiamine
• a sludge dispersant selected from the group consisting of polyisobutene with
• multiaminic head groups for example poly-iso-butylen succinimide
• diethyleneglycol monomethylether (v) diethyleneglycol monomethylether; and (vi) a solvent, selected from the group consisting of aromatic and aliphatic hydrocarbons.
• the usable initiators include the azo initiators widely known in the technical field, such as AIBN and 1 ,1 -azobiscyclohexanecarbonitrile, and also peroxy compounds such as methyl ethyl ketone peroxide, acetylacetone peroxide, dilauryl peroxide, fe/f-butyl-per-2- ethylhexanoate, ketone peroxide, ie f-butyl peroctoate, methyl isobutyl ketone peroxide, cyclohexanone peroxide, dibenzoyl peroxide, fe/f-butyl-peroxybenzoate, fe/f-butyl
• initiators are selected from the group consisting of 2,2-di(ie/f- amylperoxy)propane, ie/f-butyl peroxy acetate, dicumyl peroxide, fe/f-butyl peroxyisobutyrate, ie/f-amylperoxy 2-ethylhexanoate, dibenzoyl peroxide and 1 ,1 -di(ie/f- amylperoxy)cyclohexane.
• Suitable chain transfer agents are in particular sulfur-free compounds which are known per se.
• (a) GPC system consisting of a Waters Alliance 2695 system equipped with a Model 2414 Rl detector. Two Waters Styragel 5E columns are used with THF at a flow rate of 1 .0 mL/min and a temperature of 40°C. Calibration is performed with a broad poly(alkyl methacrylate).
• Polymer 1 grafted polyalkyl (meth)acrylate copolymer with N-dispersant monomers in backbone and grafted side-chain
• Polymer 2 statistical polyalkyl (meth)acrylate copolymer with N-dispersant monomers only in the main chain
• Polymer 3 ethylene vinyl acetate-co-polyalkyl methacrylate polymer (EVA-graft-PAMA) 20 gram of ethylene vinyl acetate (EVA) copolymer was dissolved in 150 g dilution oil (Shell Risella 907) equipped with a glass stirrer, a thermocouple and a condenser and the mixture was stirred overnight at 100°C. Later, the temperature was adjusted to 90°C. 18.8 g of C12- C15 methacrylate (dodecyl pentadecyl methacrylate, DPMA) was charged to the reaction vessel containing ethylene vinyl acetate copolymer.
• EVA-graft-PAMA ethylene vinyl acetate-co-polyalkyl methacrylate polymer
• Polymer 5 statistical polyalkyl methacrylate comprising 2-dimethylaminoethyl
• reaction temperature was reduced to 100°C after 1 .5 hours of the initial feed completion, and after 30 min, 0.2% tert- butylperoxy-2-ethylhexanoate was added and the reaction was held for another 4 hours.
• M w 8030 g/mol
• Shellsol A150 Solvent Naptha 150
• solvent Naptha 150 solvent Naptha 150
• the oil was heated to 140°C.
• a mixture of 287.5 g of a C12-C14 methacrylate, 287.5 g of C16-18 methacrylate, 34.5 g of LUPEROX® 220, and 0.17 g of n-dodecylmercaptan was prepared.
• the entire mixture was added to the round bottom flask via an addition funnel over the course of 300 minutes.
• the temperature of the reaction mixture was maintained at 140°C throughout the course of the addition. Following the complete addition of the mixture, the reaction held for an additional 30 minutes. Temperature was then lowered to 100°C and 1 .15 g of
• Polymer 9a ethylene copolymer wax
• the grafted copolymers according to the present invention are used as compatibilizers to ensure sufficient homogenization of multifunctional additive packages which comprise an antioxidant (butylated hydroxytoluene), a metal deactivator (N,N-disalicylidene-1 ,2- propandiamine), a sludge dispersant (poly-iso-butylen succinimide), and an anti-icing agent (diethyleneglycol monomethylether), and also an inert organic solvent (Shellsol A 150 ND) by stabilizing them such that no phase separation or opacity occur in the course of formulation or storage - even in the course of storage over prolonged periods, for example over several weeks - of the additive packages.
• an antioxidant butylated hydroxytoluene
• a sludge dispersant poly-iso-butylen succinimide
• an anti-icing agent diethyleneglycol monomethyl
• Additive packages composed of the components as outlined in Tables 1 a-c were prepared by mixing at 60°C. Rating of homogeneity
• Table 1 a Visual appearance @ blending temperature of 60°C
• MD Metal Deactivator: N,N-disalicylidene-1 ,2-propandiamine
• DiEGME diethyleneglycol monomethylether (purchased from Merck)
• Solvent Naphtha Shellsol A 150 ND (Shell) Table 1 b: Visual appearance @ room temperature (determined shortly after mixing)
• Polymer 1 which contains N-dispersant monomers in the backbone as well as in the grafted side-chain and shows an overall nitrogen content of 1 .2% the additive packages can be homogenized even over a longer storage time.
• Polymer 2 the precursor of Polymer 1 , which is a statistical polymer with N-dispersant monomers in the main chain and an overall nitrogen content of only 0.7% is not active enough. This precursor only contains 5.7% by weight of NVP in the polymer (less than 1 % by weight of nitrogen). Only after the grafting step, when the nitrogen content was increased to more than 1 % by weight, the desired effect was observed.
• Polymer 3 which is an EVA-graft-PAMA and Polymer 4 which contains about 1 % by weight of OH-groups also leads to phase separation of the additive package.
• Polymer 7 as a straight PAMA without dispersant functionality does not help to avoid phase separation.
• the advantage versus blend V is the homogeneity and phase stability of the package.
• the wax sedimentation was run according to the BP short sedimentation test procedure.
• An ultra low sulfur diesel with a sulfur content of ⁇ 15 ppm, containing 5% by weight of soybean oil methyl ester was used.
• Table 3a CP data: B5 Diesel Fuel, bath temperatu
• Table 3b PP data: B5 Diesel Fuel, bath temperatu
• Polymer 1 helps to reduce the cloud point (CP) after sedimentation. This can be explained by the wax dispersing activity which prevents n-paraffin wax crystals from settling down during cold storage.
• the CP after sedimentation is measured in the 20% bottom phase of the fuel sample after 16 hours sedimentation. There is nearly no change versus the original CP before sedimentation after addition of just 50 ppm of Polymer 1 .
• Polymer 1 reduces the pour point (PP) before and after sedimentation.
• the cold filter plugging point (CFPP) was not affected beyond its repeatability limits.
• Blends X-2 and X-3 are the most stable ones in contrast to the reference blend and blend X-1 .
• Blend X-1 contains an EVA-graft-PAMA compatibilizer. Phase separation occurs already after more than 10 days storage at room temperature in blend X-1.
• Blends X-2 and X-3 are stable over much longer storage periods.
• the common method to evaluate the oxidation stability of oils and fats is the Rancimat test (EN 141 12), measured at 1 10°C.
• Rancimat test EN 141 12
• a purified air stream is fed through the sample to induce the formation of volatile acids formed from the oxidation process.
• volatile acids are then carried over into a measurement vessel containing de-ionised water, in which the conductivity of the solution is measured.
• the end of induction period is measured as the conductivity increases.
• Typical induction periods for fresh rapeseed oil methyl ester (RME) are 5 to 7 h and 2 to 5 h for soybean oil methyl ester (SME).
• Aged FAME can have significantly lower Rancimat Induction Periods.
• antioxidants include BHA (butylated hydroxy anisole), BHT (butylated hydroxy toluene), TBHQ (tertiary butylated hydroxy quinone) etc., which are successfully used to improve the oxidation stability of vegetable oils and animal fats.

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