US3756954A - Rs for lubricants degraded ethylene propylene interpolymers useful as viscosity modifie - Google Patents

Rs for lubricants degraded ethylene propylene interpolymers useful as viscosity modifie Download PDF

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Publication number
US3756954A
US3756954A US00181212A US3756954DA US3756954A US 3756954 A US3756954 A US 3756954A US 00181212 A US00181212 A US 00181212A US 3756954D A US3756954D A US 3756954DA US 3756954 A US3756954 A US 3756954A
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viscosity
lubricants
oils
acid
degraded
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US00181212A
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F Abbott
N Pearson
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Lubrizol Corp
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Lubrizol Corp
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    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/02—Polyethene
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    • C08F8/00—Chemical modification by after-treatment
    • C08F8/50—Partial depolymerisation
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    • C08F2810/00—Chemical modification of a polymer
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    • C10N2040/25—Internal-combustion engines
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    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S260/00—Chemistry of carbon compounds
    • Y10S260/42—Melts used in preparation of non-cyclic aliphatic chloro-, bromo- and iodo-hydrocarbons

Definitions

  • This invention relates to new compositions of matter suitable for use as viscosity modifiers in lubricating oils. More particularly, it relates to oil-soluble compositions characterized by causing substantially no increase in the fluidity of a fuel oil at -20 C. when dissolved in said fuel oil at a concentration of 0.02% by weight, said compositions being prepared by oxidizing and degrading an ethylene-propylene interpolymer having a molecular weight of at least about 1000 by contacting the same with an oxygen-containing gas, in the presence of a minor amount of at least one aliphatic amine, at a temperature of at least about 100 C. for a period of time sufficient to effect a substantial reduction in the molecular weight of said interpolymer.
  • viscosity modifiers in lubricating oils has been known for some time. These materials are chosen for their ability to inhibit thickening of the lubricant at low temperatures and thinning at high temperatures. For many years, the viscosity index was used to measure this ability. The viscosity index was determined from the viscosity of the oil at 100 F. and 210 F., and increased in numeral value with increased effectiveness of the additive as a viscosity modifier. However, the viscosity index did not accurately reflect the behavior of the viscosity modifier at extremely low temperatures. An SAE 10W oil (including multi-grade oils such as l0W-30 and 10W-40) has for some time been required to have a viscosity at 0 F. of 24 poises or less.
  • olefin polymers including ethylene-propylene interpolymers
  • Such polymers are also used as low-temperature fluidity modifiers and pour point depressants in fuel oils; particularly valuable in this regard are certain oxidized, degraded polymers such as those described in US. Pat. 3,374,073.
  • oxidized, degraded polymers such as those described in US. Pat. 3,374,073.
  • the polymer might inhibit thickening to some extent above the pour point in a motor oil, it not only did not lower the pour point but actually inhibited the eifectiveness of pour point depressants separately added for that purpose.
  • a principal object of the present invention is to provide new compositions for use as lubricant additives.
  • a further object is to provide viscosity-modifying lubricant additives suitable for use in multi-grade motor oils.
  • Another object is to provide viscosity-modifying additives which are compatible with pour point depressants when used in lubricating oils.
  • Another object is to provide improved lubricant compositions having a decreased tendency to thicken at low temperatures and thin at high temperatures, and having a low pour point.
  • the present invention is based partly on the discovery that there is, in fact, an inverse correlation between the eflrciency of an ethylene-propylene interpolymer as a low temperature fluidity modifier in a fuel oil and its ability (as well as that of the lubricant as a whole) to respond positively to a pour point depressant in a lubricating oil.
  • polymers which are effective as fuel oil fluidity modifiers are generally unresponsive to pour point depressants in lubricants, and render the lubricant similarly unresponsive when dissolved therein; and conversely, the polymers of the present invention, which serve as excellent viscosity modifiers in lubricating oils and are responsive (thus rendering the lubricant also responsive) to the action of a pour point depressant, are generally ineifective as fluidity modifiers in fuel oils. According to the invention, this ineffectiveness is primarily shown by a failure to subtsantially increase the fluidity of a fuel oil at 20 C. when dissolved therein at a concentration of 0.02% by weight.
  • the principal ways of measuring fluidity are the Enjay Cold Flow Test and the Enjay Fluidity Test.
  • a measured quantity of fuel is placed in a can which is stored in a cold box at the test temperature (in this instance, 20 C.) for 16-24 hours.
  • a tube is then carefully inserted in to the fuel oil so as to avoid agitation thereof and a vacuum of 12 inches of mercury is applied to the system.
  • the amount of fuel discharged outside of the cold box is measured as a function of time, and the flow rate and overall percentage of fuel removed from the can are determined.
  • the effect of an additive on the low temperature fluidity of a fuel oil may be gauged roughly by its effect on the pour point thereof.
  • the compositions of this invention will cause little or no lowering of the pour point: at most, about a 10 F. change therein will be noted.
  • the oxidized, degraded interpolymers (hereinafter sometimes referred to merely as the degraded interpolymers) of this invention are derived principally from ethylene and propylene. They may include minor amounts, i.e., up to about 10% based on the amounts of monomeric ethylene and propylene units in the interpolymer, of polymerized units derived from other monomers.
  • examples of such other monomers include polymerizable monoolefins having at least 4 carbon atoms such as l-butene, 1- pentene, Z-butene, 3-hexene, 4-methyl-1-pentene, l-decene, l-nonene, Z-methylpropene, and l-dodecene. They also include polymerizable polyenes, especially dienes; e.g.,
  • conjugated dienes such as butadiene, isoprene, piperylene, 1,3-hexadiene, 1,3-octadiene, 2,4-decadiene, etc.
  • nonconjugated dienes such as 3,3-dimethyl-1,5-hexadiene, 1,9- decadiene, dicyclopentadiene, 1,19-eicosadiene, 1,4-pentadiene, 1,5-hexadiene, S-ethylidenenorbornene, etc.
  • the non-conjugated dienes are especially useful. For the most part, such other monomers contain about 4-12 carbon atoms although they may contain as many as 25 carbon atoms.
  • Copolymers containing about 20-70% (by weight) propylene units and about 30-80% ethylene units, and terpolymers containing about 25-50% propylene, about 50-70% ethylene and about 1-10% non-conjugated diene units, are especially useful for the puropses of this invention. with the copolymers being preferred.
  • the interpolymers from which the degraded, polymers are derived usually have weight average molecular weights of at least 1000 and usually about 50,000800,000, although polymers of higher molecular weight may sometimes be used. Those having molecular weights of about 80,000-600,000 are especially useful.
  • the degraded interplymers are prepared most conveniently by heating an interpolymer such as illustrated above, or a fluid solution of such interpolymer in an inert solvent, with oxygen or air in the presence of a minor amount of an aliphatic amine as described hereinafter.
  • Degradation of the interpolymer is characterized by a substantial reduction of its molecular weight.
  • the mechanism by which the interpolymer is degraded is not precisely known, nor is the chemical composition of the degraded product. It is known, however, from infrared analysis that the product contains oxygen in the form of carboxylic acid, ester and carbonyl groups.
  • An interpolymer as described above which has been degraded to the extent that its molecular weight is at least about 5% less than the molecular weight of the interpolymer before degradation is useful for the purposes of this invention.
  • compositions of this invention is illustrated by a procedure in which solution in mineral oil of (1) various ethylene-propylene copolymers, or interpolymers with diene intermonomers, and (2) a commercially available C1144 tertiary alkyl primary amine iixture are blown with air at ISO-160 C. for various eriods of time. Reactants, concentrations, reaction conditions and the like are listed in Table I, all percentages being by weight. Following degradation, the oil solutions of the interpolymers are filtered, occasionally with the addition of a diarylamine oxidation inhibitor for filtration.
  • the inert gas then functions as a carrier of oxygen and often provides a convenient means of introducing oxygen into the reaction mixture.
  • the oxygen or air may be introduced by bubbling it through the polymer solution. However, it is frequently preferred to merely blow air over the surface of the solution while subjecting it to vigorous shearing agitation.
  • the inert solvent used in preparing the fluid solution of the interpolymer is preferably a liquid hydrocarbon such as naphtha, hexane, cyclohexane, dodecane, mineral oil, biphenyl, xylene, or toluene, an ether such as diphenyl oxide, or a similar non-polar solvent.
  • the amount of the solvent is not critical so long as a suflicient amount is used to result in the fluid solution of the interpolymer.
  • Such solution usually contains about 60-95% of the solvent.
  • the mixture being degraded also contains a minor amount of at least one aliphatic amine.
  • the amine serves as a color stabilizer under the conditions of the reaction. Its use is critical to the invention since it apparently inhibits destructive oxidation leading to highly colored by-products While allowing oxidation and degradation of the polymer to the extent required.
  • the amine should, of course, be nonvolatile at the degradation temperature. It may be primary (e.g., toctylamine) secondary (e.g., diamylamine) or tertiary (e.g., tributylamine and azomethines of primary amines). Tertiary alkyl primary amines, including commercially available mixtures of C1144 amines of this type, are preferred.
  • the amount of amine used is usually about 1-5%, based on the weight of the polymer being degraded.
  • compositions of this invention can be employed in a variety of lubricating compositions based on diverse oils of lubricating viscosity, including natural and synthetic lubricating oils and mixtures thereof.
  • the lubricating compositions contemplated include principally crankcase lubricating oils for spark-ignited and compressionignited internal combustion engines including automobile and truck engines, two-cycle engine lubricants, aviation piston engines, marine and railroad diesel engines, and the like.
  • automatic transmission fluids, transaxle lubricants, gear lubricants, metal-working lubricants, hydraulic fluids, and other lubricating oil and grease compositions can benefit from the incorporation of the present compositions.
  • Natural oils include animal oils and vegetable oils (e.g., castor oil, lard oil) as well as solvent-refined or acid-refined mineral lubricating oils of the paraffinic, naphthenic, or mixed parafiinic-naphthenic types. Oils of lubricating viscosity derived from coal or shale are also useful base oils.
  • Synthetic lubricating oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, etc.); alkylbenzenes (e.g., dodecylbenzenes, tetradecylbenzene, dinonylbenzenes, di-(2-ethylhexyl)ben zenes, etc.); polyphenyls (e.g., biphenyls, terphenyls, etc.); and the like.
  • polymerized and interpolymerized olefins e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, etc.
  • alkylbenzenes e.
  • the alkyl and aryl ethers of these polyoxyalkylene polymers
  • Another suitable class of synthetic lubricating oils comprises the esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, etc.) with a varietyof alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alco hol, 2-ethylhexyl alcohol, pentaerythritol, etc.).
  • dicarboxylic acids e.g., phthalic acid, succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, etc.
  • alcohols e.g., butyl alcohol, hexyl alcohol, dodecyl alco hol, 2-ethylhexyl alcohol, pent
  • esters include dibutyl adipate, di(2 ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the Z-ethyl-hexyl diester of linoleic acid dimer, the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid, and the like.
  • Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils comprise another useful class of synthetic lubricants (e.g.,
  • tetraisopropyl silicate tetra-(Z-ethyl-hexyl) silicate, tetra-(4-methyl-2-tetraethyl) silicate, tetra-(p-tert-butylphenyl) silicate, hexyl- (4-methyl-2-pentoxy) -disiloxane, poly(methyl)-siloxanes,
  • Other synthetic lubricating oils include liquid esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decane phosphonic acid, etc.), polymeric tetrahydrofurans, and the like.
  • additives include, for example, detergents and dispersants of the ash-containing or ashless type, oxidation inhibiting agents, pour point depressing agents, extreme pressure agents, color stabilizers and anti-foam agents.
  • the ash-containing detergents are exemplified by oilsoluble neutral and basic salts of alkali or alkaline earth metals with sulfonic acids, carboxylic acids, or organic phosphorus acids characterized by at least one direct carbon-to-phosphorus linkage such as those prepared by the treatment of an olefin polymer (e.g., polyisobutene having a molecular Weight of 1000) with a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus trichloride and sulfur, white phosphorus and a sulfur halide, or phosphorothioic chloride.
  • olefin polymer e.g., polyisobutene having a molecular Weight of 1000
  • a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide,
  • the term basic salt is used to designate metal salts wherein the metal is present in stoichiometrically larger amounts than the organic acid radical.
  • the commonly employed methods for preparing the basic salts involve heating a mineral oil.solution of an acid with a stoichiometric excess of a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide at a temperature above 50 C. and filtering the re sulting mass.
  • a promoter in the neutralization step to aid the incorporation of a large excess of metal likewise is known.
  • Examples of compounds useful as the promoter include phenolic substances such as phenol, naphthol, alkylphenol, thiophenol, sulfurized alkylphenol, and condensation products of formaldehyde with a phenolic substance; alcohols such as methanol, 2-
  • Especially useful as ashless detergents are the acylated polyamines and similar nitrogen compounds containing at least about 54 carbon atoms as described in US. Pat.
  • chlorinated aliphatic hydrocarbons such as chlorinated wax
  • organic sulfides and polysulfides such as benzyl disulfide, bis- (chlorobenzyl) disulfide, dibutyl tetrasulfide, sulfurized sperm oil, sulfurized methyl ester of oleic acid, sulfurized alkylphenol, sulfurized dipentene, and sulfurized terpene
  • phosphosulfurized hydrocarbons such as the reaction product of a phosphorus sulfide with turpentine or methyl oleate
  • phosphorus esters including principally dihydrocarbon and trihydrocarbon phosphites such as dibutyl phosphite, diheptyl phosphite, dicyclohexyl phosphite, pentyl phenyl phosphite, dipentyl
  • oil-soluble composition of matter which causes substantially no increase in the fluidity of a fuel oil at 20 C. when dissolved in said fuel oil at a concentration of 0.02%; by weight, said oil-soluble composition being prepared by oxidizing and degrading an ethylene-propylene interpolymer containing about 20 to 70% propylene units and 30' to 80% ethylene units by weight having a molecular weight of about WOO-800,000 by contacting the same with an oxygen-containing gas, in the presence of a minor color stabilizing amount of at least one alkyl amine, at a temperature of at least about 100 C. for a period of time suflicient to efiect a reduction of at least about in the molecular weight of said interpolymer.
  • a lubricating composition according to claim 2 wherein the interpolymers contains about 20-70% propylene units and about 30-80% ethylene units.
  • a lubricating composition according to claim 3 wherein the amine is a mixture of C1144 tertiary alkyl primary amines.
  • a lubricating composition according to claim 4 wherein the interpolymer before degradation has a molecular weight of about 50,000-800,000.
  • a lubricating composition according to claim 4 wherein the interpolymer after degradation has a molecular weight of about 3000200,000.
  • a lubricating composition according to claim 8 wherein the terpolymer before degradation has a molecular weight of about 50,000800,000.
  • a lubricating composition according to claim 8 wherein the terpolymer after degradation has a molecular weight of about 3000-200,000.

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  • Chemical Kinetics & Catalysis (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
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US00181212A 1971-09-16 1971-09-16 Rs for lubricants degraded ethylene propylene interpolymers useful as viscosity modifie Expired - Lifetime US3756954A (en)

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AU (1) AU468893B2 (enrdf_load_stackoverflow)
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4036772A (en) * 1975-03-03 1977-07-19 The Lubrizol Corporation Esters made from the reaction product of low molecular weight ethylenically unsaturated acylating agents and oxidized ethylene-propylene interpolymers
US4068056A (en) * 1975-03-05 1978-01-10 Exxon Research And Engineering Company Aminated polymeric additives for fuel and lubricants
US4068058A (en) * 1975-03-05 1978-01-10 Exxon Research And Engineering Company Aminated polymeric additives for fuel and lubricants
US4145493A (en) * 1977-12-01 1979-03-20 Standard Oil Company (Indiana) Oxidation of rubbery polymeric hydrocarbons
US4372863A (en) * 1977-04-13 1983-02-08 Exxon Research & Engineering Co. Oil compositions containing oil-soluble, oxidatively and mechanically degraded ethylene copolymers
US4743391A (en) * 1983-03-28 1988-05-10 Chevron Research Company Method for oxidatively degrading an olefinic polymer
US4800033A (en) * 1985-05-28 1989-01-24 Karl Stetter Process for the non-cutting reshaping of metals, and lubricant compositions for this process
US4925579A (en) * 1983-06-20 1990-05-15 Chevron Research Company Lubricating oil containing hydroperoxidized ethylene copolymers and terpolymers as dispersants and V.I. improvers
US5103061A (en) * 1989-02-10 1992-04-07 Bp Chemicals Limited Synthesis of hydrocarbyl amines
RU2337944C2 (ru) * 2006-05-31 2008-11-10 Вячеслав Игоревич Унковский Способ и установка получения депрессорной присадки к дизельному топливу, депрессоная присадка и дизельное топливо
RU2372382C1 (ru) * 2008-04-29 2009-11-10 Федеральное государственное унитарное предприятие "Центральный институт авиационного моторостроения имени П.И. Баранова" Присадка для повышения термоокислительной стабильности углеводородного реактивного топлива и реактивное топливо
RU2378323C1 (ru) * 2008-06-20 2010-01-10 Ирина Николаевна Гришина Присадка к дизельному топливу, дизельное топливо
CN102776054A (zh) * 2011-05-13 2012-11-14 中国石油天然气股份有限公司 一种高抗剪切性能粘度指数改进剂的制备方法
CN104031195A (zh) * 2013-03-06 2014-09-10 中国石油天然气股份有限公司 一种粘度指数改进剂的制备方法

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5319477B2 (enrdf_load_stackoverflow) * 1974-02-13 1978-06-21
JPS5120960U (enrdf_load_stackoverflow) * 1974-08-01 1976-02-16
JPS51128953U (enrdf_load_stackoverflow) * 1975-04-12 1976-10-18
FR2533581B1 (fr) * 1982-09-23 1986-09-19 Chevron Res Composition d'huile lubrifiante contenant des copolymeres et terpolymeres ethyleniques hydroperoxydes comme dispersants et agents ameliorant l'indice de viscosite et ses applications
JPH0629390B2 (ja) * 1986-06-20 1994-04-20 住友化学工業株式会社 感圧接着剤

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4036772A (en) * 1975-03-03 1977-07-19 The Lubrizol Corporation Esters made from the reaction product of low molecular weight ethylenically unsaturated acylating agents and oxidized ethylene-propylene interpolymers
US4068056A (en) * 1975-03-05 1978-01-10 Exxon Research And Engineering Company Aminated polymeric additives for fuel and lubricants
US4068058A (en) * 1975-03-05 1978-01-10 Exxon Research And Engineering Company Aminated polymeric additives for fuel and lubricants
US4372863A (en) * 1977-04-13 1983-02-08 Exxon Research & Engineering Co. Oil compositions containing oil-soluble, oxidatively and mechanically degraded ethylene copolymers
US4145493A (en) * 1977-12-01 1979-03-20 Standard Oil Company (Indiana) Oxidation of rubbery polymeric hydrocarbons
US4743391A (en) * 1983-03-28 1988-05-10 Chevron Research Company Method for oxidatively degrading an olefinic polymer
US4925579A (en) * 1983-06-20 1990-05-15 Chevron Research Company Lubricating oil containing hydroperoxidized ethylene copolymers and terpolymers as dispersants and V.I. improvers
US4800033A (en) * 1985-05-28 1989-01-24 Karl Stetter Process for the non-cutting reshaping of metals, and lubricant compositions for this process
US5103061A (en) * 1989-02-10 1992-04-07 Bp Chemicals Limited Synthesis of hydrocarbyl amines
RU2337944C2 (ru) * 2006-05-31 2008-11-10 Вячеслав Игоревич Унковский Способ и установка получения депрессорной присадки к дизельному топливу, депрессоная присадка и дизельное топливо
RU2372382C1 (ru) * 2008-04-29 2009-11-10 Федеральное государственное унитарное предприятие "Центральный институт авиационного моторостроения имени П.И. Баранова" Присадка для повышения термоокислительной стабильности углеводородного реактивного топлива и реактивное топливо
RU2378323C1 (ru) * 2008-06-20 2010-01-10 Ирина Николаевна Гришина Присадка к дизельному топливу, дизельное топливо
CN102776054A (zh) * 2011-05-13 2012-11-14 中国石油天然气股份有限公司 一种高抗剪切性能粘度指数改进剂的制备方法
CN104031195A (zh) * 2013-03-06 2014-09-10 中国石油天然气股份有限公司 一种粘度指数改进剂的制备方法

Also Published As

Publication number Publication date
JPS511459B2 (enrdf_load_stackoverflow) 1976-01-17
FR2154058A5 (enrdf_load_stackoverflow) 1973-05-04
DE2245364A1 (de) 1973-03-22
DE2245364B2 (de) 1976-04-08
IT965343B (it) 1974-01-31
CA989100A (en) 1976-05-11
GB1352289A (en) 1974-05-08
AU4494772A (en) 1974-01-31
JPS4838307A (enrdf_load_stackoverflow) 1973-06-06
AU468893B2 (en) 1976-01-29

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