US3151076A - Oil additives and lube oils containing them - Google Patents

Oil additives and lube oils containing them Download PDF

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Publication number
US3151076A
US3151076A US16637A US1663760A US3151076A US 3151076 A US3151076 A US 3151076A US 16637 A US16637 A US 16637A US 1663760 A US1663760 A US 1663760A US 3151076 A US3151076 A US 3151076A
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Prior art keywords
oil
acid
weight
salt
acids
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US16637A
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Sydney R Epton
Hughes John
Joseph M Soesan
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Shell USA Inc
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Shell Oil Co
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F26/06—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/44—Preparation of metal salts or ammonium salts
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    • C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08—Inorganic acids or salts thereof
    • C10M2201/082—Inorganic acids or salts thereof containing nitrogen
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    • C10N2070/02—Concentrating of additives

Definitions

  • This invention relates to improved lubricating oils and additives therefor.
  • Multigrade lubricating oils have found rather wide acceptance and have certain advantages over conventional single grade lubricating oils.
  • the multigrade types are capable of effectively lubricating over a wide temperature range and at lower oil consumption, particularly at high engine speeds and temperatures.
  • the viscosity characteristics of multigrade oils are such that they remain fluid at low temperature to insure cold starting and good oil circulation during warmup, and have enough body at high temperatures to provide protection at high speed operations.
  • the viscosity reduction at the lower temperatures reduces friction, improves fuel economy and protects the engine due to the fluidity of the oil at the time the engine is started. Additionally, it is possible to omit bright stock fractions from such oils which conventional single grade oils usually contain and which tend to cause engine octane number requirement increase, surface ignition and spark plug fouling.
  • Conventional multigrade oils are usually low viscosity base oils compounded with relatively large amounts (5- of viscosity index improvers such as are sold commercially under the trade name of Paratone, Santodex and Acryloid of the 150, 618 or 710 type.
  • the first two types are hydrocarbons exemplified by polyisobutylone and condensation products containing alkyl and aryl radicals, e.g., condensation products of chlorinated wax with napthalenes or copolymers of styrene with C olefins.
  • the Acryloid polymers are oxygen-containing copolymers of dissimilar esters of acrylic acids such as copolymers of mixtures of octyl, lauryl or stearyl methacrylates.
  • the viscosity index improvers of this type are generally only effective for short periods of time due to their inability to resist mechanical degradation caused by the high shearing forces to which the polymers are subjected in the engine, their tendency to cause oxidation, gumming and the like. Under certain conditions, it has found necessary to add separate anti-oxidants to such lubricating oils.
  • the said salts are novel and are themselves a feature of the invention.
  • polymeric amine herein is meant a polymer including copolymers, containing basic nitrogen-containing groups, which may be derived from polymeriza'ole monomers containing primary, secondary or tertiary (the latter two are preferred) amino nitrogen, including basic heterocyclic amino nitrogen-containing substances having an ethylenically unsaturated polymerizable group.
  • polymeric amines are suitable for the preparation of salts which are useful in the present invention. They may be simple polymers, such as those obtained by polymerizing vinyl substituted basic heterocyclic nitrogen-containing substances such as vinyl pyridine, vinyl picoline and vinyl quinoline or vinyl arylamines such as para-aminostyrene, or polyamines prepared by reducing, in the presence of ammonia or primary or secondary amines, the polymerized acrylates and methacrylates of hydroxy alkyl tertiary amines, and the polymeric amines obtained by reacting polymers containing epoxy groups with ammonia or primary or secondary amines.
  • the preferred polymeric amine compounds are those containing tertiary amine groups and particularly those containing heterocyclic amino groups such as obtained by copolymerizing apolymerizable heterocyclic nitrogerrbase compound with a polymerizable unsaturated material free of heterocyclic nitrogen-containing radicals such as are described in British patent specification 760,544 and US. Patents 2,839,512 and 2,889,282.
  • the copolymers include copoiymer of stearyl methacrylate and Z-methyl-S- vinyl pyridine, copolymer of stearyl methacrylate, lauryl methacrlate and Z-methyl-S-vinyl pyridine, and those which contain additional C allryl methacrylates in the polymer also such as copolymer of stearyl methacrylate, lauryl methacrylate, methyl methacrylate and 2-methyl-5- vinyl pyridine, and similar copolymers in which the methyl methacrylate is replaced by butyl methacrylate and the 2-methyl-5-vinyl pyridine is replaced by 5-ethyl-2-vinyl pyridine and mixtures thereof.
  • polymeric amines are those available commercially such as those sold by E. I. du Pont de Nemours and Co. under the names LOA 564 and 565, andwhich are lauryl methacrylate/diethylaminoethylmethacrylate copolymers.
  • N-hydrocarbyl carbamic acids used to form the salts of this invention are those represented by the aboveformula and preferably N,N-substituted dithiocarbamic acid and particularly C alkyl or aralkyl aryl or cycloalkyl dithiocarbamic acid.
  • Typical of such acids are N-hydrocarbyl carbamic, thiocarbamic and dithiocarbamic acids, e.g., N-alkyl, N-aralkyl, N-aryl and N-cycloalkyl as well as N,N-alkyl, N,N-aralkyl, N,N-aryl and N,N -cycloalkyl derivatives of said acids.
  • the N-alkyl' derivatives of said acids include NC alkyl, e.g., N-methyl, N-ethyl, N-
  • N-cyclohexyl derivatives include II-cyclopentyh, N-cyclohexyL,
  • N-cycloheptyl carbamic, thiocarbamic and dithiocarbarnic acids include N,N-dimethyl-, N,N-diethyl-, N,N-dibutyl-, N,N-dihexyl-, N,N- diheptyi-, hN-dioct 'h, ⁇ LN-dinonyh, N-butyl-, N-octyl-, N,N-dibenzyl, N,N-diphenyl, N,N-dicyclohexyl-, N,N-dicycloheptyl carbarnic, thi'ocarbamic and dithiocarbamic acids.
  • N,N-disubstituted carbamic acids may optionally contain mixed hydrocarbon substituents, i.e., N-alkyl N-aryl carbamic, thiocarbamic or dithiocarbamic acids, for example, N-ethyl N-phenyl dithiocarbarnic acids, N-butyl N-phenyl dithiocarbamic acid, and N-propyl N- naphthyl dithiocarbamic acids; 1 -alkyl N-cycloalkyl dithiocarbc iic acids, for example, N-butyl N-cyclopentyl dithiocarbamic acid, N-isobutyl N-cyclohexyl dithiocarbamic acid and N-octyl N-cyclopentyl dithiocarbamic acid; N-alkyl N-aralkyl dithiocarbamic acids, for example, N-propyl N-benzyl dithiocarbamic acid, N
  • aryl and aralkyl carbamic, thiocarbamic or dithiocarbarm'c acids may optionally be substituted in the aromatic nucleus by, for example, halogen, sulfonic acid, phosphinic acid, phosphorus acid and hydrocarbon groups.
  • the N-hydrocarbyl carbamic acids may be made by any of the known methods, for example, the dithiocarbamic acids can be made by the interaction of a primary or secondary amine with carbon disulfide in a suitable solvent.
  • the free carbamic acids are unstable, and in those cases the acids can be converted to alkali metal salts of these carbamic acids and used in the manufacture of the polymeric amine salts according to the invention as hereinafter described.
  • the alkali metal salts of these carbarnic acids, preferably dithiocarbamic acids may be prepared by the interaction of the corresponding amine with carbon disulfide in the presence of aqueous alkali.
  • the salts used in accordance with this invention may be prepared by any of the conventional methods for preparing salts of organic amines and organic acids.
  • the polymeric amine may be dissolved in an organic solvent, such as benzene or xylene, and the acid added to the solution with agitation.
  • the acid itself may, of course, be dissolved in a suitable solvent.
  • the polymeric amine may be suspended in a suitable liquid medium and the acid stirred into the suspension.
  • the acid and the polymeric amine may be added to the lubricating oil to allow salt formation in situ.
  • salts used in accordance with the invention by the interaction of a salt of the oil-soluble polymeric amine with a metal, amine or ammonium salt of the carbarnic acid, e.g., dithiocarbarnic acid.
  • a salt of the oil-soluble polymeric amines there may be used, for example, the hydrochloride, hydrobrornide, carbonate, acetate or sulphate salts
  • metal salts of the said carbamic acids there may be used, for example, the potassium sodium, calcium, barium, magnesium, mercury or zinc salts.
  • a salt of the oil-soluble polymeric amine and a metal salt of the dithiocarbamic acid such that the inorganic metal salt so formed by double decomposition is insoluble in the resulting oil-soluble polymeric amine dithiocarbamate and in the solvent, as it is thereby more readily removed; for example, by filtration.
  • a typical process comprises dissolving the salt of the oil-soluble polymeric amine in an inert solvent, e.g., benzene, and adding to the solution, with stirring, a solution of the metal salt of the dithiocarbamic acid in the same solvent.
  • a precipitate of the inorganic metal salt is formed by double decomposition which is removed by filtration and the salt of the oil-soluble polymeric amine and the dithiocsrbamic acid is then isolated by distilling oil the solvent, preferably under reduced pressure.
  • the basic nitrogen-containing polymeric salts of N- hydrocarbyl carbarnic acids used in oil compositions of the present invention are novel salts and form one feature of the present invention.
  • novel salts those preferred which are derived from copolymers having a molecular weight of from about 75,060 to about 1,956,030 and derived from a vinyl pyridine and an ester or" an acrylic acid in which the acrylic acid moiety has no more than 5 carbon atoms.
  • the copolymer is one in which the molar ratio of polymerizable nitrogen base compound to polymerizable unsaturated material free of heterocyclic nitrogen-containing radicals in the copolymer is from about 1:1 to about 1'4.
  • EXAMPLE I A mixture comprising 30.9 parts of lauryl methacrylate, 3.4 parts of stearyl rnethacrylate, 9 parts by weight of methyl methacrylate, 2.5 parts of 2-rnethyl-5-vinyl pyridine, 12.5 parts of benzene and 12.5 parts neutral HVl oil is heated to C. A 5% solution of di-tbutyl peroxide in the above mixture is added over a short period of time and polymerization commences after an induction period of about one hour. At the commencement of the polymer zation Z-methyl-S-vinyl pyridine is added at such a rate as to maintain a constant 2-methyl-5-vinyl pyridine/methacrylate molar ratio of 0.069/1.
  • the quantity of Z-methyl-S-vinyl pyridine added during the polymerization is approximately equal to the amount charged initially.
  • additional 10-0 neutral HVI oil is added and the benzene removed by steam stripping to yield a concentrate containing about 30% of polymer.
  • a polymeric amine is prepared by copolyrnerizing 3900 parts of lauryl methacrylate and 228 parts of 2-methyl-5- vinylpyridine by the process described in Example I.
  • the product is obtained as a 50% concentrate in 100 neutral HVI oil.
  • benzene and a slight excess of Hill are added to form the hydrochloride.
  • 6.15 parts of potassium dibutyl dithiocarbamate in benzene are added and the preparation completed as in Example I.
  • the product is obtained as a concentrate in 100 neutral HVI oil.
  • the polymeric salts when added to lubricating oils produce an outstanding lubricant.
  • the lubricating oil can be any natural or synthetic oil having lubricating properties.
  • the oil may be of hydrocarbon lubricating oil obtained from a paraffinic or napthenic crude or a mixture thereof.
  • the viscosity of these oils may vary over a wide range, such as from 60 SUS at 100 F. to 50 SUS at 210 F.
  • the hydrocarbon lubricating oils may be blended with fatty oils, such as castor oil or lard oil, and/ or with syn thetic lubricating oils, such as polymerized olefins, co-" polymers of alkylene glycols and alkylene glycols and alkylene oxides, organic esters, such as 2k(2-ethylhexyl) sebacate, dioctyl phthalate and trioctyl phosphate, polymeric tetrahydrofurane, and polyalkyl silicone polymers, such as dimethyl silicone polymers.
  • fatty oils such as castor oil or lard oil
  • syn thetic lubricating oils such as polymerized olefins, co-" polymers of alkylene glycols and alkylene glycols and alkylene oxides, organic esters, such as 2k(2-ethylhexyl) sebacate, dioctyl phthalate and trioctyl phosphate,
  • cating oils such as polymeric hydrocarbons orthe polar containing compounds may be used as the sole base lubricating oil or admixed with fatty oils and derivatives thereof.
  • light oils of a viscosity range of 60 to 150 SUS at 100 F. are preferred of which light mineral oils of 75 to 100 SUS at 100 F. are specifically useful.
  • Lubricating compositions of the invention are illustrated by the following formulations:
  • Composition A Concentrate of salt according to Example I A mineral lubricating oil having a viscosity of 55 seconds Redwood I 13.3% by wt.
  • Composition B 8% by Weight.
  • the synthetic lubri- Composition C Concentrate of salt according to Example III A mineral lubricating oil having a viscosity of 75 seconds Redwood I at 140 F.
  • Composition D The salt of Example VI Mineral lubricating oil (75/ F. SUS) Composition E The salt of Example III Mineral lubricating oil (75/ 100 F. SUS) Composition F The salt of Example H Zn dicyclohexyl thiophosphate Mineral lubricating oil (75/ 100 F.
  • Composition G X Zn diamyl dithiocarbamate Mineral lubricating oil (100/100? F.
  • Composition H 14.5% by weight.
  • Example I The salt of Example I a- Tricresyl phosphate 3% by weight. 0.5% by weight.
  • Composition I The salt of Example I 3% by weight. Tricresyl phosphate 0.5%by weight. Dicresyl phosphate 0.2% by weight. 4,4 J methylene bis(2,6 ditertbutyl phenol) 0.75% by weight. Mineral lubricating oil Essentially balance,
  • Composition X Concentrate of the polymeric amine used in Example I 4% by weight. A mineral lubricating oil having a viscosity of 55 seconds Redwood I at 210 F. Balance.
  • compositions A and D and the base oil were subjected to an anti-oxidant test in a Dornte Oxidation Apparatus using copper stearate as catalyst according to the process described in Disc. Far.
  • compositions B to I comparable oxidation stabilizing effects to Composition A can be expected when these compositions are tested in the Dornte Oxidation Apparatus under conditions described above.
  • Lubricating compositions of this invention can be modified by addition thereto of minor amounts, such as 0.01% to 2% of conventional additives, such as viscosity index and pour point depressant, e.g. the polyalkyl methacrylates, and alliyl styrene polymers, wax naphthalene condensation products; corrosion inhibitors, e.g., inorganic and organic nitrites, such as JaNO or LiNO and diiso propylammonium nitrate or dicyclohexylammonium nitrite, extreme pressure and anti-wear agents, organic phosphites, phosphates and phosphonates, such as trichloroethyl phosphite, tricresyl phosphate and diLorol phosphate (the Word Lorol is a registered Trademark and the diLorol phosphate referred to above is an ester of Lorol alcohol and phosphoric acid, Lorol alcohol being technical lauryl alcohol obtained by reduction of
  • Solubilizers to enhance the solubility of some of the salts of this invention in lubricating oils include long-chain aliphatic alcohols and fatty acids, such as stearyl alcohol and oleic acid and partial esters, such as sorbitan monooleate.
  • a lubricating oil composition comprising a major amount of lubricating oil containing from about 0.1 to about 20% by weight of an oil-soluble salt of an oilsoluble polymeric amine selected from the group consisting of poly(vinyl pyridine), poly(vinyl picoline), poly(vinyl quinoline), and poly(paraarnino styrene), and N-C -hyclroca1'by1 carbamic acid said polymeric amine salt having a molecular weight of from 75,000 to 1,000,000.
  • a lubricating oil composition comprising a major amount of lubricating oil containing from about 0.1% to about 20% by weight of an oil-soluble salt of a copolymer of a vinylpyridine and an acrylate ester in the mol ratio of about 1:4 respectively and having a molecular Weight of from 75,000 to 1,000,000 and an N-C -alkyl thiocarbarnic acid.
  • a lubricating oil composition comprising a major amount of lubricating oil containing from about 0.1% to about 20% by weight of an oil-soluble salt of a copolymer of a vinylpyridine and an acrylate ester in the mol ratio of about 1:4 respectively and having a molecular weight of from 75,000 to 1,000,000 and an N,N-C -hydrocarbyl thiocarbamic acid.
  • a lubricating oil composition comprising a major amount of lubricating oil containing from about 0.1% to about 20% by weight of an oil-soluble salt of a copolymer of a vinylpyridine and an acrylate ester in the mol ratio of about 1:4 respectively and having a molecular s3 Weight of from 75,000 to 1,000,000 and an N,N-C -dialkyl thiocarbamic acid.
  • a lubricating oil composition comprising a major amount of mineral lubricating oil containing from about 1% to about 5% by weight of an oil-soluble salt of copolymer of stearyl methacrylate, lauryl methacrylate in the mol ratio of 4:1 respectively, and having a molecular Weight of from 75,000 to 1,000,000 and Z-methyl-S-vinylpyridine and dibutyldithiocarbamic acid.
  • a lubricating oil composition comprising a major amount of mineral lubricating oil containing from about 1% to about 5% by weight of an oil-soluble salt of copolymer of stearyl methacrylate, lauryl methacrylate in the mol ratio of 4:1 respectively, and having a molecular Weight of from 75,000 to 1,000,000 and 2-methyl-5-vinylpyridine and di-3-ethylhexyldithiocarbamic acid.
  • a lubricating oil composition comprising a major amount or" a mineral lubricating oil containing from about 1% to about 5% by weight of an oil-soluble salt of copolymer of lauryl methacrylate and diethyl aminoethyl methacrylate in the mol ratio of 4:1 respectively, and having a molecular weight of from 75,000 to 1,000,000 and dibutyldithiocarbamic acid.
  • a lubricating oil composition comprising a major amount of mineral lubricating oil containing from about 1% to about 5% by weight of an oil-soluble salt of copolymer of lauryl methacrylate and diethyl amino ethyl methacrylate in the mol ratio of 4:1 respectively, and having a molecular weight of from 75,000 to 1,000,000 and di-Z-ethylhexyl dithiocarbamic acid.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
US16637A 1959-05-28 1960-03-22 Oil additives and lube oils containing them Expired - Lifetime US3151076A (en)

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Cited By (3)

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US3230168A (en) * 1964-12-08 1966-01-18 Shell Oil Co Lubricant compositions
US3354085A (en) * 1965-05-28 1967-11-21 Chevron Res Lubricants containing quaternary ammonium dithiocarbamates
US3392192A (en) * 1965-03-24 1968-07-09 Armour Ind Chem Co Thiocarbamic acid inner salts

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US2691632A (en) * 1952-03-01 1954-10-12 California Research Corp Oil compositions resistant to oxidation
US2737496A (en) * 1952-02-16 1956-03-06 Du Pont Lubricating oil compositions containing polymeric additives
US2737452A (en) * 1952-04-07 1956-03-06 Du Pont Stabilized fuel oils
US2752311A (en) * 1952-07-26 1956-06-26 Texas Co Lubricant containing a metal derivative of a hydroxyarylakyl polaymine and a metal dithiocarbamate
US2839512A (en) * 1955-12-30 1958-06-17 Shell Dev Vinylpyridine long chain acrylic ester copolymers and their preparation
US2868728A (en) * 1955-12-30 1959-01-13 California Research Corp Salts of acrylamide-acrylic acid ester copolymers as greasethickening agents
US2889282A (en) * 1956-09-17 1959-06-02 Shell Dev Lubricating oil compositions
US2892822A (en) * 1954-12-29 1959-06-30 Du Pont Acrylate copolymers containing quaternary ammonium and tertiary amine salt units
US3012055A (en) * 1960-07-13 1961-12-05 Universal Oil Prod Co Alkyl orthophosphate salts of copolymer amines
US3030303A (en) * 1957-04-09 1962-04-17 Shell Oil Co Lubricating oil composition
US3038857A (en) * 1958-11-10 1962-06-12 Sun Oil Co Lubricants containing additives
US3062744A (en) * 1958-08-08 1962-11-06 Universal Oil Prod Co Preventing heat exchanger deposits

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US2160880A (en) * 1936-11-02 1939-06-06 Standard Oil Co Lubricant
US2737496A (en) * 1952-02-16 1956-03-06 Du Pont Lubricating oil compositions containing polymeric additives
US2691632A (en) * 1952-03-01 1954-10-12 California Research Corp Oil compositions resistant to oxidation
US2737452A (en) * 1952-04-07 1956-03-06 Du Pont Stabilized fuel oils
US2752311A (en) * 1952-07-26 1956-06-26 Texas Co Lubricant containing a metal derivative of a hydroxyarylakyl polaymine and a metal dithiocarbamate
US2892822A (en) * 1954-12-29 1959-06-30 Du Pont Acrylate copolymers containing quaternary ammonium and tertiary amine salt units
US2868728A (en) * 1955-12-30 1959-01-13 California Research Corp Salts of acrylamide-acrylic acid ester copolymers as greasethickening agents
US2839512A (en) * 1955-12-30 1958-06-17 Shell Dev Vinylpyridine long chain acrylic ester copolymers and their preparation
US2889282A (en) * 1956-09-17 1959-06-02 Shell Dev Lubricating oil compositions
US3030303A (en) * 1957-04-09 1962-04-17 Shell Oil Co Lubricating oil composition
US3062744A (en) * 1958-08-08 1962-11-06 Universal Oil Prod Co Preventing heat exchanger deposits
US3038857A (en) * 1958-11-10 1962-06-12 Sun Oil Co Lubricants containing additives
US3012055A (en) * 1960-07-13 1961-12-05 Universal Oil Prod Co Alkyl orthophosphate salts of copolymer amines

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3230168A (en) * 1964-12-08 1966-01-18 Shell Oil Co Lubricant compositions
US3392192A (en) * 1965-03-24 1968-07-09 Armour Ind Chem Co Thiocarbamic acid inner salts
US3354085A (en) * 1965-05-28 1967-11-21 Chevron Res Lubricants containing quaternary ammonium dithiocarbamates

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BE591232A (US06653308-20031125-C00064.png)
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DE1146994B (de) 1963-04-11
NL251968A (US06653308-20031125-C00064.png)

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