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Definitions

• Combustion engines such as gasoline engines and diesel engines, are more or less subject to wear of cylinders, pistons and piston rings.
• automobile engines in particular, it is a known phenomenon that considerably increased wear occurs when the cylinder temperature remains relatively low, as is the case when driving short distances. According to the general view this is due to moisture condensing on the cool cylinder walls in the presence of acids, such as sulfuric acid from sulfurous fuel, hydrochloric acids from lead scavengers, and organic acids from incompletely burnt gasoline.
• acids such as sulfuric acid from sulfurous fuel, hydrochloric acids from lead scavengers, and organic acids from incompletely burnt gasoline.
• the corrosion caused by these acids also termed cold corrosion, is responsible for much of the piston and cylinder wear in automobiles.
• the oleophilic group may be a hydrocarbon chain (R) of 83() carbon atoms attached directly to the backbone chain, e.g., C1248 straight or branched chain alkyl radical or indirectly through a polar group such as -GR groups, wherein R is as defined.
• Polymeric compounds of this type should have at least 150 carbon atoms in the backbone chain and a plurality of units (1) and (ii) as described such that the molecular weight of the polymer ranges from about 5,000 to about 1,000,000, preferably from about 50,000 to 500,000.
• the intermediate portion of the copolymers of this invention may be obtained by copolymerization of a monomer containing a carbonyl group with a monomer containing an oleophilic group having at least 8 carbon atoms, or a copolymer obtained indirectly from these monomers, for example by reducing ester groups to aldehyde groups of a polymer or copolymer containing ester groups, or for example by oxidation of secondary alcohol groups present in a polymer or copolymer to ketone groups. Also copolymers containing acetal groups and the oleophilic hydrocarbyl groups may be converted into carbonyl groups by treat ment with mineral acid.
• Examples of monomers of which the copolymers containing aldehyde groups may be composed are unsaturated aliphatic aldehydes. Preference is given to copolmers compound of acrolein or methacrolein and one or more monomers, or copolymers composed of a beta-formalitcrylic acid ester, maleic di-aldehyde or fumaric (ii-aldehyde, and one or more monomers containing the oleophilic groups.
• alpha-olefins having at least 10 carbon atoms
• esters of unsaturated organic monoand dicarboxylic acids and saturated alcohols or esters of saturated organic carboxylic acids and unsaturated alcohols, which esters contain a saturated branched or straight carbon chain having at least 8 carbon atoms, or unsaturated aliphatic ethers having a saturated branched or unbranched carbon chain containing at least 8 carbon atoms.
• mixtures or these monomers may be used, for example a mixture of stearyl methacrylate and lauryl methacrylate.
• esters of unsaturated monoand dicarboxylic acids and saturated alcohols esters of methacrylic acid are preferred, in particular methacrylic acid esters of which the ester group contains 1248 carbon atoms.
• esters of maleic acid and furnaric acid of which at least one of the ester groups contains at least 8 carbon atoms are also suitable for use.
• the copolymerization of one or more (I) monomers with one'or more (ll) monomers may be carried out in any known manner. Copolymerization may, for example, be carried out by dissolving the monomers in a solvent, such as benzene, or in a mixture of solvents, such as a mixture of benzene and ethanol. A telomerization agent, such as nitrobenzene, may also be added to the solution of the monomers. The copolymerization may be initiated, for example by a thermal treatment or by the addition, possibly at elevated temperature, of an initiator such as dibenzoyl peroxide, azo-bis-isobutyronitrile or other radical-yielding sources.
• an initiator such as dibenzoyl peroxide, azo-bis-isobutyronitrile or other radical-yielding sources.
• the optimum copolymerization temperature depends on the rate at which the initiator decomposes. If the reactivity of the monomers is so divergent that the monomer ratio in the copolymer differs considerably from the ratio in which the monomers are brought together before copolymerization, one of the monomers may be added in portions, thereby ensuring the formation of the copolymer having a homogeneous composition.
• EXAMPLE I 253.5 parts by weight of stearyl methacrylate, 507 parts by weight of benzene and 2 parts by weight of benzoyl peroxide were introduced in a 2-liter three-necked flask provided with a drop funnel, reflux cooler and gas inlet tube. Nitrogen was then passed into the flask for one hour with stirring, after which 84 parts by weight of acrolein were added. The mixture was brought to a temperature of 80 C. by means of a heating bath. After the mixture had been stirred at this temperature for one hour one part by weight of benzoyl peroxide was added, followed by 0.375 part by weight of benzoyl peroxide, after which the mixture was stirred for 18 hours at 80 C.
• the total reaction time during which the mixture was continuously stirred and nitrogen was passed into the fiask was 24 hours. After cooling the reaction mixture was poured out into 1600 partsby weight of methanol and the acrolein/stearyl methacrylate copolymer which separated was taken up in 500 parts by weight of benzene. This solution was poured out into 1600 parts by weight of methanol and the copolymer was separated washed with methanol. The copolymer was then taken up in benzene and the copolymer isolated by freeze drying from the resultant solution. The yield was 205.8 parts by weight of copolymer, i.e. 61% by weight based on the total quantity of starting monomers. The ratio of the component acrolein and stearyl methacrylate monomers in the copolymer was 1.27:1. The molecular weight, determined by the light scattering technique, was 98,000.
• the copolymer was converted by reaction with hydroxyl amine into a copolymer having oximino groups.
• the copolymer which separated was washed with methanol, dissolved in 500 parts by weight of benzene and poured out into 1600 parts by weight of methanol.
• the copolymer which separated was washed with methanol, then dissolved in 500 parts by weight of benzene, after which the resultant solution was filtered.
• the product was isolated from the filtrate by freeze drying. A quantity of 188.9 parts by weight of the copolymer containing oximino groups was obtained. Analysis showed that the ratio of the component acrolein, acrolein oxime and stearyl methacrylate monomers in this copolymer was 0.4:0.88:1.
• the resultant copolymer contained acetal groups which were split off by hydrolysis under the influence of hydrochloric acid in the following manner.
• the copolymer was dissolved in 600 parts by weight of benzene and the solution mixed with 25 parts by volume of hydrochloric acid or" 38% concentration, and 20 parts by weight of methanol. The mixture was boiled under reflux for 15 minutes and, after being cooled, subsequently poured out into 1600 parts by weight of methanol. The copolymer which separated was washed with methanol, dissolved in 500 parts by weight of benzene and the solution poured out into 1600 parts by weight of methanol. After the resultant copolymer had been washed with methanol it was re-dissolved in benzene and the copolymer was obtained from this solution by freeze drying. The yield was 256 parts by weight, i.e. 60.7 based on the total weight quantity of the monomers.
• the copolymer was converted by reaction with hydroxyl amine into a copolymer containing oximino groups.
• the ratio of acrolein/dimethyl acetalzacrolein oximezstearyl methacrylate in this copolymer was EXAMPLE III
• Acrolein and stearyl methacrylate were copolymerized under conditions identical to those of Example I, but in this case the benzoyl peroxide was added in two portions, i.e. 0.7 part direct and 0.3 part after 16.5 hours.
• the copolymer was isolated in the manner described in Example I. The yield was 56.3%.
• the monomer ratio of acroleinzstearyl methacrylate in the copolymer was 0.96:1, the molecular weight, determined by the light scattering technique, was 140,000.
• the copolymer was reacted with hydroxyl amine in the manner described in Example II, but the pH of the hydroxyl amine solution was 7.5.
• the ratio of acroleinzacrolein oximezstearyl methacrylate in the resultant product .38:0.57:l, and the nitrogen content was 2.0% by weight.
• EXAMPLE 1V Acrolein and stearyl methacryl-ate were copolymerized in benzene as solvent under the conditions of temperature, atmosphere and time as stated in Example I although not all the acrolein was aded direct to the solution of stearyl methacrylate in benzene but was distilled from a distillation flask and passed into the reaction vessel in a period of 5 hours. Half of the quantity of benzoyl peroxide 1% by weight based on the total quantity of the monomers to be copolymerized) was immediately added, after which the other half was gradually added to the reaction mixture over a period of 5 hours.
• the starting quantities were 114 parts by weight of acrolein, 338 parts by weight of stearyl methacrylate, 675 parts by weight of benzene and 4.5 parts by weight of benzoyl peroxide.
• the reaction product was isolated in the manner described in Example I.
• the yield was 290 parts by weight, i.e. 64.2%.
• the ratio of the acrolein and stearyl methacrylate monomers in the copolymer was 0.80:1 and in the copolymer 24% or" the number of aldehyde groups was present in the hydrate form.
• the molecular weight, determined by the'light scattering technique, was 162,000.
• EXAMPLE V By the method similar to the one described in Example TV but in which the acrolein was distilled from a distillation flask and passed into the reaction vessel in a period of 1.25 hours and the benzoyl peroxide was gradually added in a period of 3 hours, a copolymer was obtained in a yield of 66.5% of which the monomer composition of acrolein:acrolein hydrate:stearyl methacrylate was 1.11:0.2221. The molecular weight, determined by the light scattering technique, was 90,000.
• This copolymer was converted with hydroxyl amine obtained from the hydrochloric acid of hydroxyl amine and pyridine.
• EXAMPLE VI 98 parts by weight of acrolein diethylacetal and 5.0.7 parts by weight of stearyl methacrylate were dissolved in 120 parts by weight of benzene. A quantity of 0.5 part by weight of azo-bis-isobutyronitrile was added to this solution. The temperature of the solution was brought to 65 C. and the solution was kept at this temperature for 50 hours with stirring. After 21 and after 29 hours respective quantities of 0.25 parts by weight of azo-bisisobutyro nitriel were added. A nitrogen atmosphere was maintained during the reaction in the reaction vessel. The resultant copolymer was isolated as described in the previous examples. The yield was 51 parts by weight, i.e. 3.3%
• EXAMPLE VII 416 parts by weight of stearyl methacrylate and 106 parts by weight of methyl isopropenyl ketone were dissolved in 2088 parts by'weight of benzene. After the addition of 5.8 parts by weight of benzoyl peroxide the temperature was raised to C. and the mixture was kept at this temperature for 48 hours with stirring, refluxing of the evaporating solvent being ensured. After 6 hours 93 parts by weight of stearyl methacrylate were added as well as 5.8 parts by weight of benzoyl peroxide. After 32 hours 5.8 parts by weight of benzoyl peroxide were again added.
• the product was isolated by pouring out the mixture into methanol, taking up the copolymer which separated into benzene, by again pouring out the solution into methanol as described in the previous examples.
• the yield was 448 parts by weight of stearyl methacrylate/ methyl isopropenyl ketone copolymer.
• the ratio of the methyl isopropenyl ketone and stearyl methacrylate monomers in the copolymer was 0.137z1.
• the nitrogen of the resultant product was 0.56 part by weight.
• the ratio of the methyl isopropenyl ketone oxime and stearyl methacrylate monomers in the copolymer was 0.87:1.
• the yield was 225 parts by weight.
• phenolic antioxidants such as alkylphenol, e.g., 2,6-ditert.butyl-4-methyl phenol or p,p'-rnethylene bisphenols such as 4,4'-methylene (2,6- ditert.butyl phenol) or arylarnines such as phenyl-alphanaphthylamine and mixtures thereof.
• Anti-scufling agents include organic phosphites, phosphates, phosphonates and their thio-derivatives, such as C alltyl phosphites, or phosphonates, e.g., diand tributyl, octyl, lauryl, stea1yl, cyclohexyl, benzyl, cresyl, phenyl, phosphites or phosphates, as well as their thio-den'vatives, P S -terpene reaction products, e.g., P S -pine oil reaction product and alkali metal salts thereof such as potassium salt of a P S -terpene reaction product, phosphonates such as dibutyl methanephosphonate, dibutyl trichloromethanephosphonate, dibutyl monochlorornethanephosphonate, dibutyl chlorobenzenephosphonate, and the like.
• the oximino-containing polymeric additives of this invention improve various petroleum or synthetic products by the incorporation of a minor amount (0.001% to 10%, preferably 0.1% to 5% by Weight) of the additive.
• they may be used to improve gasoline, jet fuels, transformer oils, turbine oils, mineral lubricating oils, synthetic lubricating oils, e.g., polyolefins, esters of dibasic acid, silicone polymers, etc., industrial oils such as hydraulic fluids, metal working fluids and quenching fluids.
• the oximino-containing polymers are particularly useful in refined mineral lubricating oils, which may range from SAE 5W viscosity grade to SAE 140 grade and which may be derived from parafiinic, naphthenic or asphaltic base crudes.
• Representative oils are refined high viscosity index mineral oils having a viscosity of 100 F. of 100 to 250 SUS.
• a typical mineral lubricating oil (X) of this type is an extracted Venezuelan paraffinic lubricating oil having a viscosity of 114 cs. at 100 F. and a California mineral lubricating oil (Y) may have the following properties:
• Viscosity index (Dean and Davis) 93 Viscosity, SUS at 100 F. 103
• copolymers according to the invention may be added as such to lubricating oils.
• the product is only partly freed from the solvent, for example by steam distillation, after Which a small quantity of a lubricating oil is added and the remainder of the solvents is finally distilled off by means of steam, preferably under reduced pressure.
• the resultant concentrate can then be diluted with a lubricating oil.
• compositions are representative of this invention:
• Composition A Example I copolymer 2% wt. Mineral lubricating oil (X) Balance.
• Composition B Example II copolymer 2% wt. Mineral lubricating oil (X) Balance.
• Composition C Example III copolymer 2% wt. Mineral lubricating oil (X) Balance.
• Composition D Example 1V copolymer 2% wt. Mineral lubricating oil (X) Balance.
• Composition E Example V copolymer 2% wt. Mineral lubricating oil (X) Balance.
• Composition F Example I copolynier 2% wt. 4,4-methylene bis(2,6-ditert. butyl phenol) 0.75% wt. Mineral lubricating oil (X) Balance.
• Composition G Example I copolyiner wt. 4,4-methylene bis(2,6-ditert. butyl phenol) 0.5% wt. T ricresyl phosphate 0.8 wt. Mineral lubricating oil (X Balance.
• compositions of the present invention were engine tested in a (1) Caterpillar diesel engine, (2) Gardner diesel engine, (3) Petter gasoline engine and in (4) a C.F.R. gasoline engine and the results were as follows:
• Caterpillar Diesel Engine Water-cooled, single-cylinder, four-stroke engine The test lasted 48 hours.
• the fuel was a gas oil having a sulfur content of 0.9% by Weight.
• the cooling Water temperature was about 80 C.
• the engine power was 18 H.P., bore 146 mm., stroke 203.2 mm., swept volume 3.4 liters.
• Gardner Diesel Engine Water-coled, single-cylinder, four-stroke engine The test lasted 17 hours.
• the fuel was a gas oil having a sulfur content of 0.9% by weight.
• the cooling water temperature was about 80 C.
• the engine power was 11 H.P., bore 108 mm., stroke 152.4 mm., swept volume 1.4 liters.
• Water-cooled, single-cylinder, four-stroke engine bore 85 mm., stroke 82.5 mm., swept volume 468 cu. cm.
• the test lasted 28 hours.
• the fuel was a motor gasoline having 1.2 ml. TEL per U.S. gallon and a sulfur content of 0.05% by weight.
• the cylinder cooling water temperature was approximately C.
• the temperature of the cooling water of the cooled valve cover was approximately 20 C.
• Cooled single-cylinder, four-stroke engine bore mm., stroke 82.5 mm., swept volume 368 cu. cm.
• the fuel was a motor gasoline having 1.2 ml. TEL per US. gallon and a sulfur content of 0.05% by Weight.
• the cooling liquid temperature was approximately 160 C.
• Lubricating compositions of this invention are particularly applicable for high temperature, high speed use as in aviation engines, automotive engines, truck engines as well as industrial equipment.
• An improved mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from 0.1% to by weight of an oil-soluble polyoximino-containing copolymer obtained by polymerizing at reflux temperature and in the presence of a free radical initiator a polymerizable unsaturated carbonyl containing compound selected from the group consisting of a low molecular Weight olefinic ketone and a low molecular weight olefinic aldehyde and C1248 alkyl methacrylate in the mol ratio of from about 0.1:1 to about 220.1, respectively, and reacting said copolymer with hydroxylamine at a pH of 7-10, to etiect conversion of the carbonyl groups to oximino groups, said copolymer having a molecular Weight of from 50,000 to 1,000,000.
• An improved mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from 0.1% to 10% by weight of an oil-soluble polyoximino-containing copolymer obtained by polymerizing at reflux temperature and in the presence of benzoyl peroxide catalyst acrolein and C alkyl methacrylate in the mol ratio of from about 0.111 to about 2:01, respectively and reacting said copolymer with hydroxyl amine at a pH of 7-8 to effect conversion of the carbonyl groups to oximino groups, said copolymer having a molecular Weight of from 50,000 to 500,000.
• An improved mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from 0.1% to 10% by weight of an oil-soluble polyoximino-containing copolymer obtained by polymerizing at reflux temperature and in the presence of benzoyl peroxide catalyst acrolein and stearyl methacrylate in the mol ratio of from about 0.1:1 to about 2:0.1, re-
• copolymer i0 spectively and reacting said copolymer with hydroxyl amine at a pH of 7-8 to effect conversion of the carbonyl groups to oximino groups, said copolymer having a molecular Weight of from 50,000 to 500,000.
• An improved mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from 0.1% to 10% by weight of an oil-soluble polyoXimino-containing copolymer obtained by polymerizing at reflux temperature and in the presence of azo-bis-isobutyronitrile catalyst acrolein, diethylacetal and stearyl methacrylate in the mol ratio of from about 0.1:1 to about 2:0.1, respectively and reacting said copolymer with hydroxyl amine at a pH of 7-8 to effect conversion of the carbonyl group to oximino groups, said copolymer having a molecular weight of from 50,000 to 500,000.
• An improved mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from 0.1% to 10% by weight of an oil-soluble polyoXimino-containing copolymer obtained by polymerizing at reflux temperature and in the presence of benzoyl peroxide catalyst methyl isopropenyl ketone, and stearyl methyacrylate in the mol ratio of from about 0.1:1 to about 220.1, respectively and reacting said copolymer with hyd-roxyl amine at a pH of 7-8 to effect conversion of the carbonyl groups to oximino groups, said copolymer having a molecular Weight of from 50,000 to 500,000.

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