Fuel oil composition

The present invention relates to a fuel oil composition containing an additive composition and an additive concentrate of the additive composition for improving low temperature flow characteristics.

Fuel oils derived from petroleum or plant sources are components that tend to settle large crystals of wax or spherites at low temperatures, such as forming gel structures that impair the flow capacity of the fuel oils, such as n-. Including alkane. The lowest temperature at which fuel still flows is known as the pour point. When the temperature of the fuel drops and reaches the pour point, it becomes difficult to transfer the fuel by line and pump. In addition, wax crystals tend to clog fuel lines, screens and filters at temperatures above the pour point. These problems are well recognized in the art and various additives have been proposed to reduce the pour point of fuel oils, many of which are commercially used. Similarly, other additives that reduce the size of the wax crystals formed and change their shape have been proposed and are used commercially. Crystals of smaller size are desirable because they are less likely to clog the filter. The wax derived from diesel fuel, which is mainly alkane wax, crystallizes as a plate; several additives suppress this and make the wax needle-like, and the resulting needle-like material is filtered from the plate. Easy to pass through. Additives also have the effect of retaining the formed crystals in suspension in the fuel, reducing sedimentation and also helping to prevent blockage.

US 5,998,530, registered by Krull et al. In December 1999, improves the fluidity of mineral oils and mineral oil distillates when used in combination with ethylene / vinyl ester copolymers and paraffinic dispersants. Alkylphenol aldehyde resins useful in the above are disclosed. In certain examples, resins made from the monoalkylphenols nonylphenol and butylphenol are used. EP 311,452, published October 8, 1987, discloses an alkylphenol-formaldehyde condensate. EP 311,452 teaches to minimize dialchelate products and maximize monoalchelates in order to achieve a number average molecular weight of at least 3000, preferably at least 7000. Preferably, the alkylphenol-formaldehyde condensate comprises about 90-100 mol% (eg 95-100 mol%) of monoalkylated phenol. EP 311,452 teaches that the dialchelate molecule stops the growth of the chain and therefore the amount of dialchelate monomer that can be "acceptable" is preferably 0-10 mol%.

<p> An object of the present invention is to provide an improved additive composition for improving the low temperature flow characteristics of a fuel oil. More specifically, the present invention presents a low temperature of a fuel oil having a final boiling point of 330-390 ° C and a boiling temperature range of 90% -20% measured according to ASTM D-86, preferably 80-160 ° C. The purpose is to improve the flow characteristics.</p>

<p> According to the present invention, a condensation reaction product of an aliphatic aldehyde having 1 to 4 carbon atoms and an alkylphenol mixture containing a large amount of monoalkylphenol and a monofunctional dialkylphenol in an amount of more than 10 mol% and less than 35 mol% is included. A high molecular weight additive with a number average molecular weight (Mn) of 1,000 to less than 3,000, preferably Mn of 1,000 to 2,500 is contained in an amount of improving low temperature fluidity and a large amount of fuel oil is contained, and the number of carbon atoms of the alkyl group of the phenol is 1. Fuel oil compositions of ~ 20, preferably 4-12 have been found.</p>

The condensation reaction product preferably contains 12-33 mol%, more preferably 14-30 mol% dialkylphenol. The alkyl group of phenol preferably has 4 to 12, more preferably 4 to 11, and even more preferably 5 to 10 carbon atoms. The alkyl group of the monoalkylphenol is preferably branched. Preferably, at least one of the alkyl groups of the dialkylphenol is branched, and more preferably both of the alkyl groups of the dialkylphenol are branched. The dialkylphenol is preferably di-nonylphenol, di-t-butylphenol or C.₁₂It is a branched dialkylphenol. The term "monofunctional" as described herein in relation to dialkylphenol means that only one side is available in the phenyl ring for condensation reactions with aldehydes. The preferred dialkylphenol for use in the present invention is usually substituted with alkyl at the 2- and 4-positions of the phenyl ring. As a result of the use of such monofunctional dialkylphenols alone, the molecular weights of the high molecular weight condensation reaction products are at the 2-, 4- and 6-positions, for example, as explained in Formula II of EP 311,452. Compared to the products disclosed in EP 311,452, which are condensates made from trifunctional dialkylphenols with available reaction sites, they are relatively low, with Mn of approximately 1000 to less than 3000.

The aldehyde used to produce the condensation product is preferably formaldehyde, and the condensation reaction is alkaline or, for example, using the methods well known in the art or disclosed in US 5,998,530. It is carried out with an acidic catalyst and in the presence of organic solvents such as toluene and xylene that form an azeotropic mixture with water and at a temperature of about 90-200 ° C. INDUSTRIAL APPLICABILITY The present invention provides the use of the additive composition for improving the low temperature flow characteristics of a fuel oil. The additive composition is particularly effective in intermediate distillate fuel oils having a final boiling point of 330-390 ° C and a boiling temperature range of 90% -20% measured according to ASTM D-86, preferably 80-150 ° C. It was found to be the target. The present invention further provides an additive concentrate containing a solvent miscible with the fuel oil and a small amount of the additive composition.

The fuel oil may include atmospheric or depressurized distillates, cracked gas oils, or straight runs and thermally and / or catalytically cracked distillates in any proportion. The most common petroleum distillate fuels are kerosene, jet fuel, diesel fuel, heating oil and heavy fuel oil. The heating oil may be a straight atmospheric distillate, or may contain decompression gas oil, decomposed gas oil, or both. The fuel may also contain large or small amounts of components derived by the Fischer-Tropsch method. Fischer-Tropsch fuels, also known as FT fuels, include those described as gas-liquid fuels, coal and / or biomass energy conversion fuels. Syngas (CO + H) to produce such fuels₂) Is generated first, and then converted to normal paraffin by the Fischer-Tropsch method. Normal paraffins and olefins are then modified by methods such as catalytic decomposition / modification or isomerization, hydrocracking and hydrogen isomerization to give various hydrocarbons such as isoparaffin, cycloparaffin and aromatic compounds. .. The resulting FT fuel can be used as is or in combination with other fuel components and fuel types, such as those described herein. The cold fluidity problems mentioned above are most commonly found in diesel fuels and heated oils. The present invention is also applicable to fuel oils containing fatty acid methyl esters derived from vegetable oils such as rapeseed methyl esters, which are used alone or in combination with petroleum distillates. The additive concentration in the oil may be, for example, the mass per mass (active ingredient) of the fuel in the range of 0.1 to 1000 ppm, preferably 1 to 500 ppm, and more preferably 1 to 100 ppm. Additives are bulk oils (bulk) by methods known in the art. Can be introduced during oil). If more than one additive component or co-additive component should be used, such components can be introduced into the oil together or separately in any combination.

Concentrates containing the additive dispersed in the carrier liquid (eg in solution) are advantageous as a means of introducing the additive. The concentrate of the present invention is advantageous as a means for introducing additives into bulk oils, such as distillate fuels, which can be introduced by methods known in the art. The concentrate may also contain other additives as required, and preferably 3 to 75% by weight, more preferably 3 to 60% by weight, most preferably 10 to 50% by weight. May be preferably contained in the oil solution. Examples of carrier liquids are hydrocarbon solvents such as petroleum fractions such as naphtha, kerosenes, diesel and organic solvents including heating oils; aromatic hydrocarbons such as aromatic fractions such as'SOLVESSO'under the trade name. For sale in; alcohols such as isodecanol and 2-ethylhexanol and / or esters; and paraffinic hydrocarbons such as hexane and pentane and isoparaffinic. Alkylphenols such as nonylphenol and 2,4-di-t-butylphenol have been found to be particularly useful as carrier solvents, either alone or in combination with any of the above. The carrier liquid must, of course, be selected taking into account its compatibility with the additive and the fuel. The additives of the present invention can be introduced into bulk oils by other methods, such as those known in the art. If co-additives are required, they can be introduced into the bulk oil at the same time as or at different times as the additives of the present invention. Preferably, the condensed polymer of the present invention is used in a fuel oil in combination with one or more conventional low temperature fluid additives defined in (A)-(E) below.

(A) Ethylene Polymers Each polymer can be a homopolymer or a copolymer of ethylene and other unsaturated monomers. Suitable comonomeres are hydrocarbon monomers such as propylene, n- and iso-butylene, 1-hexene, 1-octene, methyl-1-pentenevinylcyclohexane and various α-olefins known in the art such as 1 Includes decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene and mixtures thereof. Preferred comonomeres are unsaturated esters or ether monomers, with ester monomers being more preferred. Preferred ethylene unsaturated ester copolymers have units of the following formula in addition to the units derived from ethylene: -CR¹R²-CHR³-(In the formula, R¹Represents hydrogen or methyl; R²Is COOR⁴(In the formula, R⁴Is linear, alkyl groups with 1-12 carbon atoms, preferably 1-9 carbon atoms, or branched if the number of carbon atoms is 3 or higher) or OOCR⁵(In the formula, R⁵Is R⁴Or represents hydrogen); and R³Is hydrogen or COOR⁴Represents).

These may include copolymers of ethylene with ethylene-based unsaturated esters or derivatives thereof. An example is a copolymer of ethylene with an ester of a saturated alcohol and an unsaturated carboxylic acid, preferably the ester of which is an unsaturated alcohol and a saturated carboxylic acid. Ethylene vinyl ester copolymers are advantageous; ethylene vinyl acetate, ethylene vinyl propionate, ethylene vinyl hexanoate, ethylene-vinyl 2-ethylhexanoate, ethylene-vinyl octanoate, ethylene-vinyl versatate. Copolymers are preferred. Preferably, the copolymer comprises 5-40% by weight vinyl ester, more preferably 10-35% by weight vinyl ester. For example, US Mixtures of the two copolymers as described in 3,961,916 may be used. The Mn of the copolymer is advantageously 1,000-10,000. If desired, the copolymer may include units derived from additional comonomer, such as terpolymers, tetrapolymers or higher polymers, for example, the additional comonomer may be isobutylene or diisobutylene or an additional unsaturated ester. In the case of.

(B) Comb Polymers Comb polymers are described in Comb-Like Polymers. Structure and Properties, NA Plate and VP Shibaev, J. Poly. Sci. Macromolecular Revs., 8, p 117-253 (1974). .. In general, comb polymers are branched chain chains, eg, hydrocarbyl branched chains with 6-30 carbon atoms, eg 10-20 carbon atoms, optionally intervened with one or more oxygen atoms and / or carbonyl groups. What can be made of molecules that hang from the polymer backbone, the branched chains of which are directly or indirectly attached to the backbone. Examples of indirect bonds include bonds via intermediate inserted atoms or chains, which may include covalent and / or ionic bonds, such as those in salts. Comb polymers are generally distinguished by having a minimum molar proportion of units containing such long-chain branched chains.

Examples of preferred comb polymers include those containing the units of the following general formula:-(CDE-CHG) m- (CJK-CHL) n- (in the formula, D is R.¹¹, COOR¹⁰, OCOR¹⁰, R¹¹COOR¹⁰Or OR¹⁰; E stands for H or D; G stands for H or D; J stands for H, R¹¹, R¹¹COOR¹⁰, Or a substituted or unsubstituted aryl or heterocyclic group; K is H, COOR¹¹, OCOR¹¹, OR¹¹Or represents COOH; L is H, R¹¹, COOR¹¹, OCOR¹¹Or represents a substituted or unsubstituted aryl; R¹⁰Represents a hydrocarbyl group with 10 or more carbon atoms; and R¹¹Is R¹¹COOR¹⁰The hydrocarbylene (divalent) group in the group, and separately the hydrocarbyl (monovalent) group, and m and n represent the molar ratio, the total of which is 1, and m is a finite number of 1 or less. And n is 0 to less than 1, preferably m is in the range 1.0 to 0.4 and n is in the range 0 to 0.6). R¹⁰Advantageously represents a hydrocarbyl group having 10 to 30, preferably 10 to 24, more preferably 10 to 18 carbon atoms. Preferably R¹⁰Is a linear or slightly branched alkyl group, R¹¹Advantageously represents a hydrocarbyl group having 1 to 30 carbon atoms, preferably 6 or more, more preferably 10 or more, preferably 24 or less, more preferably 18 or less, in the case of monovalent. .. Preferably R¹¹Is a linear or slightly branched alkyl group in the case of monovalent. R¹¹Is preferably a methylene or ethylene group in the case of divalent. "Slightly branched" means having a single methyl branch.

Comb polymers may contain units derived from other monomers, if desired or if desired, examples of which are CO, vinyl acetate and ethylene. It is also within the scope of the present invention to include two or more different comb polymers. The comb polymer may be a copolymer of maleic anhydride and other ethylenically unsaturated monomers such as α-olefins or unsaturated esters such as vinyl acetate, as described in EP-A-214,786, for example. Good. A molar ratio of 2: 1 to 1: 2 is appropriate and equivalents of comonomer are preferred, but not essential. For example, examples of olefins that can be copolymerized with maleic anhydride include 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene and styrene. Other examples of comb polymers include polyalkyl (meth) acrylates. The copolymer can be esterified by suitable techniques, preferably maleic anhydride and fumaric acid at least 50% esterified, but this is not required. Examples of alcohols that can be used include n-decane-1-ol, n-dodecane-1-ol, n-tetradecane-1-ol, n-hexadecane-1-ol, and n-octadecan-1-ol. Can be mentioned. Alcohols may contain up to 1 methyl branch per chain, as described in EP-A-213,879, eg 2-methylpentadecane-1-ol, 2-methyltridecane-1-. It may be oar. The alcohol may be a mixture of linear and monomethyl branched alcohols. For example, it is preferable to use pure alcohol over commercially available alcohol mixtures; when using a mixture, the number of carbon atoms in the alkyl group should be the average number of carbon atoms in the alkyl group of the alcohol mixture; 1 When an alcohol containing a branched chain at the position or 2-position is used, the number of carbon atoms in the alkyl group is set to the number in the linear main chain component of the alkyl group of the alcohol.

Copolymers can also react with primary and / or secondary amines such as mono- or di-hydrogenated tallow amines. Comb polymers may be, in particular, those described in fumarate or itakonate polymers and copolymers, such as EP-A-153 176, 153 177, 156 577 and 225 688 and WO 91/16407. The comb polymer is preferably C_8-12Dialkyl fumarate-vinyl acetate copolymer. Other suitable comb polymers are α-olefin polymers and copolymers, styrene and maleic anhydride esterified copolymers and styrene and fumaric acid esterified copolymers as described in EP-A-282,342; 2 or 3 types. A mixture of the above comb polymers can be used according to the present invention, and as mentioned above, such use may be advantageous. Other examples of comb polymers are hydrocarbon polymers such as copolymers of at least one single chain 1-alkene and at least one long chain 1-alkene. Single chain 1-alkenes are preferably C_3-81-Alkene, more preferably C_4-61-Alkene. Long-chain 1-alkenes preferably have a carbon atom number higher than 8 and a maximum of 20. Long chain 1-alkenes are preferably C_10-141-Alkene, including 1-decene, 1-dodecene and 1-tetradecene (see, eg, WO 93/19106). The comb polymer is preferably a copolymer of at least one 1-dodecene and at least one 1-butene in a ratio of 1-dodecene 60-90 mol% to 1-butene 40-10 mol%, preferably 1 -Dodecene 75-85 mol% vs. 1-butene 25-15 mol%. Preferably, the comb polymer is a mixture of two or three or more comb polymers made from a mixture of two or three or more 1-alkenes. Preferably, the number average molecular weight of such copolymers as measured by gel permeation chromatography on polystyrene standards is, for example, up to 20,000 or 40,000, more preferably 4,000 to 10,000, even more preferably 4,000 to 6,000. Hydrocarbon copolymers can be prepared using methods known in the art, such as Ziegler-Nattatype, Lewis acid or metallocene catalysts.

(C) Polar Nitrogen Compounds Such compounds have the formula&gt; NR.¹³(In the formula, R¹³Is an oil-soluble polar nitrogen compound containing 1 or 2 or more, preferably 2 or 3 or more substituents (representing a hydrocarbyl group having 8 to 40 atoms), and the substituent or 1 or 2 or more of the substituents is , May be in the cation form derived from them. The oil-soluble polar nitrogen compound can generally act as a wax crystal growth inhibitor in fuel. It comprises, for example, one or more of the following compounds: by reacting at least 1 mol of hydrocarbyl-substituted amine with 1 mol of hydrocarbyl acid having 1 to 4 carboxylic acid groups or its anhydride. Amine salts and / or amides formed, formula&gt; NR¹³Substituents in the formula-NR¹³R¹⁴Has, where R¹³Is defined as above, R¹⁴Is hydrogen or R¹³Represents, however, R¹³And R¹⁴May be the same or different, and the substituents form part of the amine salt and / or amide group of the compound. Esters / amides having a total carbon number of 30 to 300, preferably 50 to 150 may be used. These nitrogen compounds are described in US 4,211,534. Suitable amines are mainly C_12-40Primary, secondary, tertiary or quaternary amines or mixtures thereof, short chain amines may be used, provided that the resulting nitrogen compound is oil-soluble and is usually a total carbon atom. The condition is that the number is about 30 to 300. The nitrogen compound is preferably at least one linear C._8-40, Preferably C_14-24Contains an alkyl group of.

Suitable amines include primary, secondary, tertiary or quaternary amines, preferably secondary amines. The tertiary and quaternary amines simply form amine salts. Examples of amines include tetradecylamines, cocoamines, and hydrogenated tallow amines. Examples of secondary amines include di-octadecylamine, di-cocoamine, di-hydrogenated tallow amine and methylbehenylamine. Also suitable are amine mixtures, such as those derived from natural materials. The preferred amine is a secondary hydrogenated tallow amine, the alkyl group of which is approximately C.₁₄4%, C₁₆31% and C₁₈Derived from hydrogenated tallow consisting of 59%. Examples of suitable carboxylic acids and their anhydrides for producing nitrogen compounds are ethylenediamine tetraacetic acid, cyclic skeleton-based carboxylic acids such as cyclohexane-1,2-dicarboxylic acid, cyclohexene-1,2- Included are 1,4-dicarboxylic acids, including dicarboxylic acids, cyclopentane-1,2-dicarboxylic acids and naphthalenedicarboxylic acids, and dialkylspirobislactone. Generally, these acids have about 5 to 13 carbon atoms in the cyclic component. Preferred acids useful in the present invention are benzenedicarboxylic acids such as phthalic acid, isophthalic acid, and terephthalic acid. Phthalic acid and its anhydrides are particularly preferred. A particularly preferred compound is an amide-amine salt formed by reacting 1 mole of phthalic anhydride with 2 moles of dihydrogenated tallow amine. Another preferred compound is the diamide formed by dehydrating this amide-amine salt.

Another example is an amine salt of a long chain alkyl or alkylene substituted dicarboxylic acid derivative, eg, a monoamide of substituted succinic acid, examples of which are known in the art and are described, for example, in US 4,147,520. Suitable amines may be those described above. Other examples are those described in condensates, such as EP-A-327427. Another example of a polar nitrogen compound is a compound containing a ring system having at least two substituents of the following general formula in the ring system: -A-NR.¹⁵R¹⁶(In the formula, A is a linear or branched aliphatic hydrocarbylene group optionally intervening with one or more heteroatoms, R.¹⁵And R¹⁶Is a hydrocarbyl group having 9 to 40 carbon atoms, which may be the same or different, each independently and optionally intervening with one or more heteroatoms. Substituents may be the same or different, and the compound may optionally be in its salt form). Advantageously, A has 1 to 20 carbon atoms, preferably a methylene or polymethylene group. Such compounds are described in WO 93/04148 and WO 94/07842. Another example is the free amine itself, because they can also act as wax crystal growth inhibitors in the fuel. Suitable amines include primary, secondary, tertiary or quaternary amines, preferably secondary ones. Examples of amines include tetradecylamine, cocoamine and hydrogenated tallow amine. Examples of secondary amines include di-octadecylamine, di-cocoamine, dihydrogenated tallow amine and methylbehenylamine. Amine mixtures, such as those derived from natural materials, are also suitable. The preferred amine is a secondary hydrogenated tallow amine, the alkyl group of which is approximately C.₁₄4%, C₁₆31% and C₁₈Derived from hydrogenated tallow consisting of 59%

(D) Polyoxyalkylene compounds Examples include polyoxyalkylene esters, ethers, esters / ethers and mixtures thereof, in particular at least one, preferably at least two Cs._10-30A polyoxyalkylene glycol group containing a linear alkyl group and having a molecular weight of up to 5,000, preferably 200 to 5,000, and the alkyl group in the polyoxyalkylene glycol has 1 to 4 carbon atoms. These materials form the object of EP-A-0061895. Other such additives are listed in US 4,491,455. Preferred esters, ethers or esters / ethers have the following general formula: R³¹-O (D) -OR³²(In the formula, R³¹And R³²May be the same or different, (a) n-alkyl (b) n-alkyl-CO- (c) n-alkyl-CO (CH)₂)_x-Or (d) n-alkyl-CO (CH)₂)_xRepresenting -CO-, x is, for example, 1 to 30, the alkyl group is a linear group having 10 to 30 carbon atoms, and D is the polyalkylene group of glycol (the number of carbon atoms of the alkylene group). Represents 1-4), eg polyoxymethylene, polyoxyethylene or polyoxytrimethylene groups (substantially linear); some branched chains with lower alkyl side chains (eg in polyoxypropylene glycol). Although) may be present, the glycol is preferably substantially linear). D may also contain nitrogen.

Examples of suitable glycols are substantially linear polyethylene glycols (PEGs) and polypropylene glycols (PPGs) with a molecular weight of 100-5,000, preferably 200-2,000. Esters are preferred, and fatty acids with 10-30 carbon atoms are useful for reacting with glycols to form ester additives, C._18-24Fatty acids, especially behenic acid, are preferably used. Esters can also be produced by esterifying polyethoxylated fatty acids or polyethoxylated alcohols. These materials can also be prepared by alkylation of fatty acid esters of polyols (eg, ethoxylated sorbitan tristearate with the trade name TWEEN65, available from Uniqema). Where polyoxyalkylene diesters, diethers, ethers / esters and mixtures thereof are suitable as additives and small amounts of monoethers and monoesters (which are often formed during the manufacturing process) may be present. Diesters are preferred for use in distillates with a narrow boiling range. It is preferable that a large amount of dialkyl compound is present. In particular, stearic acid or behenic acid diesters of polyethylene glycol, polypropylene glycol or polyethylene / polypropylene glycol mixtures are preferred. Other examples of polyoxyalkylene compounds are those described in Japanese Patent Publication No. 2-51477 and Japanese Patent Publication No. 3-34790, and esterified alkoxyls described in EP-A-117108 and EP-A-326356. It is an esterified amine.

(E) 2-block hydrocarbon polymers These polymers can be obtained by terminal polymerization of linear diene, at least one crystalline block, and 1,2-constitutive polymerization of linear diene, branched chain diene. It may be an oil-soluble hydrogenated block diene polymer containing at least one non-crystalline block, which can be obtained by polymerization or a combination of such polymerizations. Advantageously, the block copolymer is derived from butadiene alone before hydrogenation, or butadiene and the general formula CH.₂= CR¹-CR²= CH₂(In the formula, R¹Is C_1-8Represents the alkyl group of R²Is hydrogen or C_1-8Contains units derived from at least one comonomer of (representing an alkyl group of). Advantageously, the total number of carbon atoms in the comonomer is 5 to 8, and the comonomer is advantageously isoprene. Advantageously, the copolymer contains at least 10% by weight of units derived from butadiene. In addition, the additive composition includes one or more conventional co-additives known in the art, such as detergents, antioxidants, corrosion inhibitors, defoamers, defoamers, and reduced metal activity. It may contain an agent, an antifoaming agent, a setan value improver, an auxiliary solvent, a packaging adapting agent, a lubricating additive and an antistatic agent. Hereinafter, the present invention will be specifically described with reference to simple examples.

The low temperature fluidity improving properties of the novel additive of the present invention are evaluated in four types of petroleum distillates, which are listed in Table 1 below.<u style="single">table 1</u><img file="JP2005298823A_D0001.tif" />

Tables 2-5 below list the results of using these fuels in the low temperature filter clogging point (CFPP) test, the details of which are described in European Standard Law EN116. The CFPP test is recognized as a standard bench test for measuring fuel performance at low temperatures and is itself incorporated into many national fuel standards. The results shown are the average of many reported trials. In the table below, "AFPC" is a conventional nonylphenol-formaldehyde condensation product made from monoalkylphenols with Mn ~ 1500; the other compounds described are monofunctional di-nonylphenols or 2,6. -The nonylphenol-formaldehyde condensate of the present invention produced by introducing di-t-butylphenol. WASA is the reaction product of di-hydride tallow amine and phthalic anhydride; EVA-1 is an ethylene-vinyl acetate copolymer with a vinyl acetate content of 36% by mass; EVA-2 is , Is an ethylene-vinyl acetate copolymer with a vinyl acetate content of 13% by mass; "EVE" is an ethylene-vinyl acetate copolymer with a vinyl acetate content of 28% by mass and a vinyl 2-ethylhexanoate content with a vinyl acetate content of 6% by mass. It is a mixture with 40% by weight ethylene-vinyl acetate-vinyl 2-ethylhexanoate copolymer; "FVA-1" is a mixture of nC.₁₂And nC₁₄It is a copolymer of alkyl fumarate and vinyl acetate; "FVA-2" is a mixed nC₁₄And nC₁₅It is a copolymer of alkyl fumarate and vinyl acetate; "FVA-3" is nC₁₂It is a copolymer of alkyl fumarate and vinyl acetate; "ppm ai" indicates the fraction by mass of the active ingredient without considering the diluent or carrier oil. In all data, the condensates of the invention, i.e. condensates made from dialkylphenols above 10 mol% up to 35 mol%, showed improvements over condensates made from monoalkylphenols.

<u style="single">Table 2</u>Fuel A<img file="JP2005298823A_D0002.tif" /><u style="single">Table 3</u>Fuel B (processed with MDFI)<img file="JP2005298823A_D0003.tif" />

<u style="single">Table 4</u>Fuel C<img file="JP2005298823A_D0004.tif" /><u style="single">Table 5</u>Fuel D<img file="JP2005298823A_D0005.tif" />