JPS6247860B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to hydroxymethylol aromatic compounds suitable as additives for oil-based lubricants having lubricating viscosity and for normally liquid fuels.
In particular, it relates to hydroxymethylol aromatic compounds having substituents containing at least about 50 aliphatic carbon atoms and methylol or substituted methylol groups. Hydrocarbon substituted phenols containing methylol or substituted methylol groups are known in the art. For example, U.S. Patent No. 3306938
No. 2912395, No. 3127251, and British Patent No. 634960. A bis(methylolhydroxy-alkylbenzyl) compound is obtained by reacting an alkylphenol having an alkyl substituent with a molecular weight of 400 to 5000 with formaldehyde, and this compound has cleaning and dispersing properties in oil. It is reported that there are. See, eg, US Pat. No. 3,737,465. This patent also discloses a number of resinous phenol formaldehyde condensation products with high molecular weight and complex structure. Over the past several decades, a number of additives have been developed to improve the performance characteristics of lubricants and normally liquid fuels. However, increasingly severe operating conditions, scarcity of raw materials, environmental concerns, and increasing costs necessitate the development of new additives for fuels and lubricants. Accordingly, an object of the present invention is to provide a novel hydroxymethylol aromatic compound suitable as a lubricant and fuel additive, and a method for producing the same. The hydroxymethylol aromatic compounds of this invention have the formula (wherein R ⁰ is an alkyl substituent having about 50 to about 300 carbon atoms in a homo- or interpolymer of monoolefins having 2 to 10 carbon atoms, and m is 1 or 0) It is indicated by. R ⁰ is an alkyl substituent having about 50 to about 300 carbon atoms, such as ethylene, propylene, 1
-Butene, 2-butene, isobutene, pentenes, hexenes, and other monoolefins having 2 to 10 carbon atoms (preferably 1-monoolefin), such as monoolefins or monoolefins having up to 10 carbon atoms, are used alone or as interpolymers. This R ⁰ is about 70 or about
Preferably it has 200 carbon atoms. A specific class of such preferred polymers are those obtained by the Lewis acid catalyzed polymerization of olefin mixtures containing primarily (ie, greater than 50%) isobutene. Another preferred class of polymers is primarily (i.e., greater than 50 mole percent) isobutene repeat units.

It contains [Formula]. The method for producing the olefin polymer or its halogenated or hydrogenated halogenated analogue as an intermediate for the substituent R ⁰ does not need to be described in detail here and will be clear to those skilled in the art. For example, the section ``Olefin Polymers - Higher Polyolefins'' in Kirk-Osmer's ``Encyclopedia of Chemical Technology,'' 2nd edition, Vol. 14, pp. 309-313, published by Interscience Publications (1963). reference. These substituents R ⁰ can be bonded to the benzene nucleus by the method described in detail below. The hydroxymethylol compounds of this invention have the formula (where R ⁰ is the same as in formula ()) by reacting a hydroxyaromatic compound of formula (2) with formaldehyde or its equivalent at a temperature up to about 160°C. To obtain the compound represented by the above formula (), intermediates such as olefin homopolymers or interpolymers or their halogenated analogs are usually mixed with aluminum trichloride, boron trifluoride, zinc chloride, etc. Mix with phenol at a temperature of about 10 to 200°C in the presence of a suitable catalyst. For example, U.S. Pat.
See No. 3368972. Substituent R ⁰ can also be introduced by other alkylation methods well known in the art. For example, the above-mentioned "Encyclopedia of Chemical Technology"
“Alkylation” in Volume 1, pages 894-895.
See section ``Of Phenols.'' To introduce a methylol group into a compound of formula (), the compound of formula () is reacted with formaldehyde or its equivalent. Here, the equivalent is a substance (eg, solution, polymer, hydrate, etc.) that reacts as formaldehyde under the conditions of the reaction, such as paraformaldehyde, formalin, and methylal. Methylol groups are introduced by reacting hydroxyaromatic compounds of formula () with formaldehyde or its equivalent in the presence or absence of acidic or alkaline reagents. When this reaction is carried out in the presence of the above-mentioned reagents, a portion of the reaction mixture usually becomes acidic or alkaline due to the decomposition of the aldehyde that occurs in situ. When the hydroxyaromatic intermediate is added in excess, the excess portion performs this function. However, in general, the reaction with formaldehyde or its equivalent is carried out in the presence of an alkaline reagent such as an alkali metal or alkaline earth metal oxide, hydroxide or lower alkoxide.
Perform at temperatures up to 160°C. Other alkaline reagents include sodium carbonate, sodium bicarbonate, sodium acetate, sodium propionate,
Examples include pyridine and hydrocarbon amines such as methylamine and aniline. Naturally, mixtures of two or more of these bases can also be used. Preferably, the reaction is carried out at a temperature of about 30 to about 125°C.
It is preferably carried out at a temperature of 70 to 100°C. In the reaction, there are no particular limitations on the relative proportions of the hydroxyaromatic intermediate and formaldehyde or its equivalent. Generally, 0.1 to 5 equivalents of formaldehyde and about 0.05 to 10.0 equivalents of alkaline reagent per equivalent of hydroxyaromatic intermediate.
It is sufficient to use an equivalent amount. Here, the term "equivalent" when used with respect to a hydroxyaromatic intermediate is equal to the weight divided by the number of unsubstituted aromatic carbons having hydrogen atoms divided by the molecular weight. "Equivalent" when used with respect to formaldehyde or equivalents thereof means the weight required to produce one mole of formaldehyde monomer. The equivalent amount of an alkaline reagent is the amount that makes a 1N solution when dissolved in 1 liter of a solvent (eg, water). Therefore, one equivalent of the alkaline reagent neutralizes 1N hydrochloric acid or sulfuric acid (ie, brings the pH to 7). Reactions involving compounds of formula () generally include:
Conveniently this is carried out in the presence of a volatile or non-volatile substantially inert organic diluent. The diluent may dissolve all or only some of the reactants, but in either case it accelerates the reaction rate by increasing contact between the reactants. However, it must not substantially affect the reaction under the conditions under which the reaction is being carried out. Suitable diluents include naphtha, textile benzine, benzene, toluene, hydrocarbons such as xylene, mineral oils (preferably), synthetic oils (described above), isopropanol, butanol, isobutanol, amyl alcohol, ethylhexanol, etc. Examples include alcohols, ethers such as mono- or diethyl ether of triethylene or diethylene glycol, and mixtures of two or more of these. The reaction between the compound of formula () and formaldehyde or its equivalent is 0.5 to 8, depending on factors such as reaction temperature, amount and nature of the alkaline reagent used.
Time arises. Control and influence of the above factors are within the skill of those skilled in the art. Once the reaction has reached the desired extent, the reaction is stopped by neutralizing the reaction mixture if an alkaline reagent was used. This neutralization can be carried out with a suitable acidic substance, typically mineral acids, organic acids or their anhydrides. Acidic gases such as carbon dioxide, hydrogen sulfide, and sulfur dioxide are also used. Generally, neutralization is carried out with carboxylic acids, especially lower alkanoic acids such as formic acid, acetic acid or propionic acid. Mixtures of these acids may also be used. Moreover, this neutralization is carried out at a temperature of about 30 to 150°C. A sufficient amount of neutralizing agent is used to substantially neutralize the reaction mixture. "Substantially neutralize" means to neutralize the reaction mixture between 4.5 and 8.0.
Means to be in the PH range. Typically, the reaction mixture will have a PH value of a minimum of about 6.0 or a maximum of about 7.5. The reaction product, i.e., the hydroxymethylol aromatic compound of the present invention, can be recovered from the reaction mixture by means of distillation, evaporation, etc. after filtration (e.g., to remove neutralization products of the alkaline reagent). . Such means are well known to those skilled in the art. It is often not necessary to isolate the hydroxymethylol aromatic compounds of this invention from the reaction solvent. This is especially true when it is mixed into fuels and lubricants, or when it is used as an intermediate in further reactions. In this case, reagents for further reactions (such as those described below) may be added directly to the product mixture, or the reaction mixture may be filtered to remove any solids present and the filtrate may be used for further reactions. It's okay. When the aforementioned reaction temperatures are high, ie above about 100° C., significant amounts of ether condensate are obtained. This condensation product has the general formula (where q is 2 to about 10). When a strong acid, such as a mineral acid, is used for the neutralization, it is important to control the amount added so that the PH value of the reaction mixture does not fall below the above-mentioned value. For example, at low pH values, overcondensation occurs and methylene-bridged phenols are produced. Such methylene bridged phenols do not fall within the scope of this invention. However, if carboxylic acids are used, such problems do not occur. This is because carboxylic acid has sufficiently low acidity and does not promote overcondensation. Also,
If it is a carboxylic acid, there is no need to strictly control the amount used. Examples of this invention will be described below. In the examples, all "parts" and "%" are by weight unless otherwise indicated, and molecular weights are determined by vapor phase osmosis (VPO) or gel permeation chromatography (GPC). In addition, the benzine used for textiles has a boiling point of approximately 63 to 79 degrees Celsius at 760 torr.
is an aliphatic petroleum naphtha. Example 1A 4885 parts of polyisobutenyl chloride having a viscosity of 1306 SUS at 99°C and containing 4.7% chlorine was added to a mixture of 1700 parts of phenol, 118 parts of sulfuric acid-treated clay and 141 parts of zinc chloride at 110-155°C. I added it over time. Then, add this mixture to 155-185
It was kept at 0.degree. C. for 3 hours and filtered through diatomaceous earth. The filtrate was vacuum stripped to 165°C/0.5 torr. The residue was filtered again through diatomaceous earth. The filtrate was substituted phenol with an OH content of 1.88%. Example 1B To a mixture consisting of 453 parts of the substituted phenol obtained in Example 1A and 450 parts of isopropanol, 42 parts of a 20% aqueous sodium hydroxide solution was added at 30° C. over 0.5 hour. 60 parts of textile grade benzine and 112 parts of a 37.7% formalin solution were then added over 0.8 hours at 20°C and the reaction mixture thus obtained was maintained at 4-25°C for 92 hours. Additionally, 50 parts of textile benzene, 50 parts of isopropanol, and 58 parts of a 50% aqueous acetic acid solution were added. The pH of the above mixture was 5.5 (according to ASTM D-974). Add this mixture to magnesium sulfate
Dry over 20 parts and then filter through diatomaceous earth. The filtrate was vacuum stripped to 25°C/10 torr. The residue was the desired methylol substitution product with an OH content of 3.29%. Example 2A Number average molecular weight (n) is 1000 (VPO) and 4.2%
Polyisobutenyl chloride 4220 containing chlorine
1,516 parts of phenol and 2,500 parts of toluene were added at 60°C with 76 parts of aluminum chloride. This mixture was held at 95° C. for 1.5 hours while blowing nitrogen gas from below the surface. 50 parts of 37.5% hydrochloric acid were added at room temperature and the mixture was left to stand for 1.5 hours. Then, it was washed 5 times with a total of 2500 parts of water and heated to 215℃/
Vacuum stripping was performed to 1 torr. Residue at 150℃
It was filtered through diatomaceous earth to improve transparency.
The filtrate has an OH content of 1.39%, a Cl content of 0.46%,
It was a substituted phenol of n898 (VPO). Example 2B To a mixture consisting of 1399 parts of the substituted phenol obtained in Example 2A, 200 parts of toluene, 50 parts of water and 2 parts of 37.5% hydrochloric acid was added 38 parts of paraformaldehyde at 50°C and held for 1 hour. This mixture was heated to 150℃/
Vacuum stripping was performed to 15 torr and the residue was filtered through diatomaceous earth. Filtrate has an OH content of 1.60
%, n1688 (GPC), weight average molecular weight (w)
2934 (GPC) was the desired product. In addition,
This product was a viscous oil with no clear boiling point or melting point, although it was a viscous oil with no clear boiling point or melting point. Ta. Example 3A 3.8 parts of boron trifluoride was added to 168 parts of phenol through a spargeer from below the surface of the phenol at 49 to 53°C.
It was implemented over time. To this is added a solution containing 678 parts of polyisobutene with n of 1600 and 133 parts of benzene.
Add 519 parts over 1.7 hours at 54-57°C;
It was held for 2.3 hours. To this mixture was added 6.5 parts of 26% ammonia water at 56-58°C over 1 hour, and at 69°C.
It was held for 0.67 hours. The mixture was filtered through diatomaceous earth and the filtrate was vacuum stripped to 228°C/15 torr. The residue was a substituted phenol with an OH content of 0.91% and n of 1439 (VPO). Example 3B A mixture of 3740 parts of the substituted phenol obtained in Example 3A, 1250 parts of textile benzene and 2000 parts of isopropanol was added with a 25% aqueous sodium hydroxide solution.
352 parts were added at 34°C. Further, 480 parts of 37.7% formalin solution was added at 34°C over 0.75 hours. The mixture thus obtained was kept at 30-34°C for 114 hours. Add to this 150 parts of commercially available glacial acetic acid and diluent oil.
3663 parts were added at 30°C. Then add this mixture to 50
Vacuum stripping was performed to ℃/30 torr. The residue was filtered through diatomaceous earth. The filtrate was a 49% oil solution of the desired product with an OH content of 1.33%. Example 4 A mixture of 5200 parts of substituted phenol, 1200 parts of toluene, and 1200 parts of isopropanol obtained in the same manner as in Example 3A except that n of the polyisobutene used was 940 (VPO) was added with 842 parts of a 25% aqueous sodium hydroxide solution. portion was added at 35°C. To this mixture, 600 parts of a 37.7% formalin solution was added at 35°C over 0.33 hours, and the mixture was maintained at 35-30°C for 15 hours. Thereafter, 400 parts of a 37.7% formalin solution was further added, and the mixture was maintained at 30°C for 20 hours. In addition, commercially available
416 parts of 37.5% hydrochloric acid was added. The pH of this mixture is 6
It was hot. Furthermore, 2000 parts of benzene and 1500 parts of toluene were added, and the mixture was azeotroped to 95° C. under partial vacuum. Add 2000 parts of diluent oil and bring the mixture to 95
Vacuum stripping was performed to ℃/30 torr. The residue was filtered through diatomaceous earth. Filtrate has OH content
It was a 30% oil solution of 1.69% of the desired product. Example 5 200 parts of benzene was added to 1110 parts of the azeotropic product obtained in Example 4, and the temperature was raised to 160°C and maintained for 3 hours. The mixture was filtered through diatomaceous earth at 150°C and the filtrate was vacuum stripped to 150°C/10 torr. The residue has an OH content of 1.73%,
n is 5252 (GPC) and w is 2171 (GPC)
The desired product was This product is a condensate of the product of Example 4. Example 6 A mixture of 2240 parts of substituted phenol obtained in the same manner as in Example 2A except that n of the polyisobutene used was 940 (VPO) and 1271 parts of diluent oil was added with 8 parts of a 50% aqueous sodium hydroxide solution and para. Add 145 parts of formaldehyde at 60°C, and add this at 80°C.
It was held for 22 hours. An additional 6 parts of glacial acetic acid were added and the mixture was kept at 150°C for 2 hours and then filtered through diatomaceous earth. The filtrate was a 35% oil solution of the desired product with 1.10% OH content. This product was condensed because it was held at a temperature exceeding 100°C, but before this temperature was held (before condensation),
It was a viscous oil with no clear boiling or melting point. Example 7 32 parts of a 50% aqueous sodium hydroxide solution and 290 parts of paraformaldehyde were added to a mixture of 4480 parts of the substituted phenol used in Example 6 and 3099 parts of diluent oil.
It was added at 40-50°C and held at 80-85°C for 14 hours. Then, 36 parts of glacial acetic acid were added at 60°C. The mixture was kept at 110-130°C for 12 hours and filtered through diatomaceous earth. The filtrate was a 40% oil solution of the desired product with an OH content of 1.05%. This product was condensed because it was held at a temperature exceeding 100°C, but before this temperature was held (before condensation),
It was a viscous oil with no clear boiling or melting point. Example 8 8 parts of a 50% aqueous sodium hydroxide solution and 145 parts of paraformaldehyde were added to a mixture of 2080 parts of the substituted phenol obtained in Example 4 and 1400 parts of diluent oil.
C. and held at 70-78.degree. C. for 7 hours. A further 9 parts of glacial acetic acid were added at 60°C and the mixture was held at 130°C for 6 hours. The residue is 99% with an OH content of 1.28%
It was a 40% oil solution of the desired product with a viscosity of 884 SUS at °C. This product was condensed because it was maintained at a temperature exceeding 100°C, but before this temperature was maintained (before condensation), it was a viscous oil with no clear boiling point or melting point. The hydroxymethylol aromatic compounds of this invention and their condensation products are useful as rust preventives and preservatives for fuels and lubricants. The aromatic compounds of the present invention are also useful as intermediates for producing compounds that act in fuels and lubricants as detergents and dispersants for sludge produced in natural engines. The hydroxymethylol aromatic compounds of this invention and their condensation products can be added to a variety of lubricants based on a variety of oils having a lubricating viscosity, such as natural oils, synthetics, or mixtures thereof.
These lubricant compositions include crankcase lubricants for spark ignition and compression ignition internal combustion engines, such as automobile and truck engines, two-stroke engines, marine and railroad diesel engines, and the like. They are also used in gas engines, stationary engines, turbines, etc. Additionally, they are useful in automatic transmission fluids, transmission shaft lubricants, gear lubricants, metalworking lubricants, pressure fluids, and other lubricating oil and grease compositions. Natural oils useful in making these compositions include animal and vegetable oils (e.g., castor oil and lard oil), as well as liquid petroleum or paraffinic, naphthenic, or mixed paraffinic-naphthenic solvent-treated or There are acid-treated mineral lubricating oils. Oils of lubricating viscosity derived from coal or shale are also useful base oils. Synthetic lubricants include
Polymerized and interpolymerized hydrocarbon oils such as olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, etc.) and halo-substituted hydrocarbon oils, poly(1-hexene), poly(1-hexene), -octene), poly(1-decene), etc. or mixtures thereof, alkylbenzenes (e.g. dodecylbenzenes,
Tetradecylbenzenes, dinonylbenzenes,
di-(2-ethylhexyl)-benzenes, etc.),
Examples include polyphenyls (eg, biphenyls, terphenyls, alkylated polyphenyls), alkylated diphenyl ethers, alkylated diphenyl sulfides, and derivatives, analogs, and homologs thereof. Polymers and copolymers of alkylene oxide, as well as derivatives thereof whose terminal hydroxyl groups have been modified by esterification, etherification, etc., also constitute another group of known synthetic lubricating oils. Examples of this include oils obtained by polymerizing ethylene oxide and propylene oxide, alkyl and aryl ethers of these polyoxyalkylene polymers (e.g. methylpolyisopropylene glycol ether with an average molecular weight of 1000, Diphenyl ether of polyethylene glycol, molecular weight
1000-1500 polypropylene glycol), or their mono- and polycarboxylic acid esters, such as acetic acid esters, mixed _C3 - _C8 fatty acid esters or _C13 oxoacid diesters of tetraethylene glycol. Other suitable groups of synthetic lubricating oils include dicarboxylic acids (e.g. phthalic acid, succinic acid, alkylsuccinic acid, alkenylsuccinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid) dimer, malonic acid, alkylmalonic acid, alkenylmalonic acid, etc.) and various alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol, etc.). Consists of esters. Specific examples of these esters are as follows.
Namely, dibutyl adipate, di(2-ethylhexyl) sebacate, dinormalhexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, and linoleic acid dimer. 2-ethylhexyl diester, a complex ester of 1 mole of sebacic acid, 2 moles of tetraethylene glycol, and 2 moles of 2-ethylcaproic acid, etc. Esters useful as synthetic oils also include:
There are those made from _C5 - _C12 monocarboxylic acids and polyols, and polyol ethers such as trimethylolpropane, pentaerythritol, dipentaerythritol, and tripentaerythritol. Silicone-based oils such as polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils also constitute another useful group of synthetic lubricants (e.g., tetraethyl silicate, tetraethyl silicate, Isopropyl, tetra(2-ethylhexyl) silicate, tetra(4-methyl-hexyl) silicate, tetra(para-tert-butylphenyl) silicate, hexyl-(4-methyl-2-pentoxy)-disiloxane, poly(methyl) ) siloxanes, poly(methylphenyl)siloxanes, etc.). Other synthetic lubricating oils include liquid esters of phosphorus-containing acids (eg, tricresyl phosphate, trioctyl phosphate, diethyl ester of decanephosphonic acid, etc.), polymerized tetrahydrofurans, and the like. Unrefined, refined and rerefined oils of the types described above may be used in the lubricant compositions of this invention. Unrefined oils are those obtained directly from natural or synthetic sources without additional refining treatment. For example, sierre oil obtained directly by retorting, petroleum oil obtained directly by distillation, or ester oil obtained directly by esterification and used without further treatment are unrefined oils. .
Refined oils are similar to unrefined oils except that they have been treated with one or more refining steps to improve one or more properties. The above purification methods are well known to those skilled in the art. For example, solvent extraction, secondary distillation, acid or base extraction, filtration, percolation, etc. Rerefined oils are obtained by applying the processes used to obtain refined oils to already used refined oils. Such rerefined oils are also known as reclaimed oils and are often further processed by methods to remove spent additives and oil breakdown products. Generally, to obtain a satisfactory lubricant composition, the hydroxymethylol aromatic compound of this invention is dissolved or stably dispersed in a proportion of 0.1 to 10 parts by weight per 100 parts of oil. The lubricant compositions may contain, in addition to the products of this invention, other additives commonly used in lubricants.
Such additives include, for example, ash-forming and ashless auxiliary detergent and dispersants, antioxidants, pour point depressants, antifoam agents, extreme pressure agents, and color stabilizers. The fuel compositions of this invention are typically liquid fuels (usually carbonized such as motor gasoline as specified in ASTM Specification D-439-73, diesel fuel or fuel oil as specified in ASTM Specification D-396). Contains a large amount of hydrogen petroleum fraction). Alcohols, ethers, organic nitro compounds, etc. (e.g. methanol, ethanol, diethyl ether,
Normally liquid fuel compositions consisting of non-hydrocarbons (methyl ethyl ether, nitromethane) are also suitable for this purpose, as are fuel oils derived from vegetable and mineral sources such as corn, purple corn, shale and coal. falls within the scope of the invention. Fuel oils consisting of mixtures of any of the above may also be used. Examples of such mixtures include gasoline and ethanol, diesel fuel and ether, gasoline and nitromethane, etc. Particularly preferred is gasoline (i.e.
It is a mixture of hydrocarbons with a 10% distillation point of 60°C according to ASTM and a 90% distillation point of about 205°C). Generally, the fuel compositions contain a sufficient amount of the hydroxymethylol aromatic compound of this invention to impart antioxidant and/or dispersing and detergent properties to the fuel. Usually, this amount will be from about 1 to about 10,000 parts by weight, preferably from 4 to 1,000 parts per million parts of fuel. Preferred gasoline-based fuel compositions generally exhibit excellent engine oil sludge dispersion and cleaning properties, as well as oxidation resistance. The fuel compositions of this invention may contain, in addition to the products of this invention, other additives known in the art. Additives include anti-knock agents such as tetraalkyl lead compounds, lead scavengers such as haloalkanes (e.g. ethylene dichloride, ethylene dibromide), anti-settling agents/modifiers such as triaryl phosphates, and dyes. , cetane improvers, antioxidants such as 2,6-di-tert-butyl-4-methylphenol, rust inhibitors such as alkylated succinic acids and their anhydrides, bacterial growth inhibitors, gum inhibitors, These include metal deactivators, demulsifiers, upper cylinder lubricants, anti-icing agents, etc. In preferred fuel compositions of this invention, aromatic compounds of this invention are used in conjunction with other ashless dispersants in gasoline. Such ashless dispersants preferably contain a mono- or polyol;
Esters with high molecular weight mono- or polycarboxylic acylating agents in which the acyl moiety has at least 30 carbon atoms. Such esters are well known in the art. For example, French Patent No. 1396645, British Patent No. 981850 and British Patent No. 1055337, as well as US Patent No.
Same No. 3579450, Same No. 3542680, Same No. 3381022
No. 3639242, No. 3697428, No. 3697428, No.
3708522; see also UK Patent No. 1306529. Generally, from about 0.1 to about
10.0 parts, preferably from about 1 to about 10 parts, of the aromatic compound of this invention are used. In another embodiment of this invention, the aromatic compounds of this invention are used in combination with Mannitz condensation products formed from substituted phenols, aldehydes, polyamines, and aminopyridines. Such condensation products are described in US Pat. No. 3,649,659, US Pat. No. 3,558,743, US Pat. The hydroxymethyl aromatic compounds of this invention may be added directly to the fuels and lubricants described above to form fuel and lubricant compositions, or they may be added directly to the fuels and lubricants described above, or they may be added to mineral oils, xylene, or other normally liquid fuels such as those described above. diluted with at least one substantially inert normally liquid organic solvent/diluent to form a concentrate;
This concentrate may then be added to fuels and lubricant oils to form the fuel and lubricant compositions described above. The concentrates generally contain from about 20 to about 90% by weight of the hydroxymethylol aromatic compound of this invention. This concentrate also contains the usual additives mentioned above,
In particular, ashless dispersants may also be included in the proportions mentioned. The remainder of this concentrate is solvent/diluent. In addition to acting as additives as described above, the aromatic compounds of this invention are used as intermediates for compounds that are also useful as additives in the fuels and lubricating oils mentioned above. For example, the methylol-substituted phenols of this invention can be condensed with amines or polyamines having at least one >NH group to provide useful engine sludge dispersants/detergents. Such condensation is conveniently carried out by heating the mixture of the methylol-substituted phenol and amine in the presence of benzene or toluene with azeotropic distillation of by-product water. For details of such condensation see French Patent No. 7507709.

Claims (1)

[Claims] 1 formula (wherein R ⁰ is an alkyl substituent having about 50 to about 300 carbon atoms in a homo- or interpolymer of monoolefins having 2 to 10 carbon atoms, and m is 1 or 0) A hydroxymethylol aromatic compound represented by 2 formulas (wherein R ⁰ is an alkyl substituent having about 50 to about 300 carbon atoms in a homo- or interpolymer of monoolefins having 2 to 10 carbon atoms) with formaldehyde or its equivalent at temperatures up to about 160°C. (Here, R ⁰ is as described above, and m is 1 or 0.) A method for producing a hydroxymethylol aromatic compound. 3. The manufacturing method according to claim 2, wherein the reaction is carried out in the presence of an alkaline reagent or an acidic reagent. 4. The manufacturing method according to claim 3, wherein the alkaline reagent is an oxide, hydroxide, or lower alkoxide of an alkali metal or alkaline earth metal. 5. The manufacturing method according to claim 2, 3 or 4, characterized in that the reaction is carried out at a temperature of about 30 to about 125°C. 6. The manufacturing method according to claim 2, 3 or 4, characterized in that the reaction is carried out at a temperature of about 70 to about 100°C.