EP0565661A1 - A biodegradable chain bar lubricant - Google Patents

A biodegradable chain bar lubricant

Info

Publication number
EP0565661A1
EP0565661A1 EP92921368A EP92921368A EP0565661A1 EP 0565661 A1 EP0565661 A1 EP 0565661A1 EP 92921368 A EP92921368 A EP 92921368A EP 92921368 A EP92921368 A EP 92921368A EP 0565661 A1 EP0565661 A1 EP 0565661A1
Authority
EP
European Patent Office
Prior art keywords
composition
groups
parts
derived
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP92921368A
Other languages
German (de)
English (en)
French (fr)
Inventor
Paul C. Naegely
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lubrizol Corp
Original Assignee
Lubrizol Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lubrizol Corp filed Critical Lubrizol Corp
Publication of EP0565661A1 publication Critical patent/EP0565661A1/en
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/04—Fatty oil fractions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
    • C10M129/92—Carboxylic acids
    • C10M129/93—Carboxylic acids having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
    • C10M129/95—Esters
    • C—CHEMISTRY; METALLURGY
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02—Sulfurised compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
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    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/10—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing aromatic monomer, e.g. styrene
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    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
    • C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
    • C10M145/14—Acrylate; Methacrylate
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    • C10M145/16—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate polycarboxylic
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • C10N2040/32—Wires, ropes or cables lubricants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/34—Lubricating-sealants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/36—Release agents or mold release agents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/38—Conveyors or chain belts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/42—Flashing oils or marking oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/44—Super vacuum or supercritical use
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses

Definitions

  • TITLE A BIODEGRADABLE CHAIN BAR LUBRICANT
  • This invention relates to a biodegradable chain bar lubricant composition and more particularly to a chain bar lubricant containing a triglyceride.
  • a typical chain bar lubricant composition has mineral oil as its base fluid. During operation of a chain saw much of the lubricant from the chain bar is deposited on the ground. This composition is not biodegradable. As a result, typical chain bar lubricant compositions remain in the environment after use for a great period of time causing considerable pollution particularly of the waterbed. As is generally known, one liter of such compositions is sufficient to render about 1 million liters of water unfit for human consumption.
  • U.S. Patent 3,860,521 (Aepli et al., January 14, 1975) provides an aqueous lubricating concentrate for lubricating continuously moving conveyor systems wherein said concentrate contains a fatty acid soap and a surfactant, wherein the improvement comprises the addition to said composition of monostearyl acid phosphate in an amount from about 0.15 to about 1.75 weight percent of the concentrate.
  • the concentrate when diluted with water is then ready for use as a lubricating composition.
  • U.S. Patent 3,170,539 (Snay et al. , February 23, 1965) relates to lubricating and more specifically to a method of and means for automatic lubrication of mechanism such as dairy conveyors with a lubricant such as a soap, water and water softening additive mixture.
  • U.S. Patent 4,740,324 discloses biodegradable tenacious compositions comprising a biodegradable lubricating oil and a biodegradable resinous component selected from the group consisting of colophonium-containing resins, colophonium and mixtures thereof. These compositions have utility as lubricants or as mold release agents.
  • U.S. Patent 2,866,729 (Zimpel, December 30, 1958) relates to a quenching oil composition for use in the metallurgical industries and to the method of quenching metals therewith.
  • the quenching oil composition comprises a mineral oil base containing a critical amount within the range of from about 1.75% to about 3.0% by weight and preferably between 2.0% and 3.0% of an artifical resin prepared by polymerizing cycloalkene hydrocarbons or lower polymers thereof with linolenic acid oils and their derivatives.
  • the biodegradable chain bar lubricant may also include (D) at least one pour point depressant and (E) at least one antiwear agent.
  • DETAILED DESCRIPTION OF THE INVENTION Generally this invention provides biodegradability to a chain bar lubricant composition.
  • the essential components are: (A) at least one triglyceride; (B) at least one viscosity modifying additive; and (C) at least one tackifier.
  • (D) at " least one pour point depressant and (E) at least one antiwear agent may also be included.
  • biodegradable describes a property which allows a compound to be broken down into smaller innocuous components which generally leave no long lived toxic residues and thus no contamination of the environment.
  • the industry wide biodegradability test employed for the instant invention is the CEC L33-T82.
  • the triglycerides of this invention are either a synthetic or naturally occurring triglyceride. Preferred is the naturally occurring triglyceride.
  • the triglycerides are of the general formula
  • esters having at least one straight chain fatty acid moiety and a glycerol moiety wherein the fatty acid moiety contains R 1, R2 and R3 which are saturated or unsaturated aliphatic hydrocarbon groups containing from about 8 to about 22 carbon atoms, preferably from about
  • Naturally occurring triglycerides having utility in this invention are exemplified by corn oil, cottonseed oil, peanut oil, olive oil, palm oil, palm kernel oil, sunflower oil, high oleic sunflower oil, coconut oil, sa flower oil, rapeseed oil, low erucic rapeseed oil, canola oil, soybean oil, lard oil, beef tallow oil, and menhaden oil.
  • sunflower oil especially high oleic acid sunflower oil obtained from sunflower (Helianthus sp.) available from SVO Enterprises, Eastlake, Ohio as Sunyl® high oleic sunflower oil.
  • the fatty acid moieties are such that the triglyceride has a monounsaturated character. That is, any one or all of R 1, R2 and R3 possess monounsaturation.
  • the monounsaturation content of the triglyceride is at least 60%, preferably 70% and most preferably 80%.
  • a triglyceride comprised exclusively of an oleic acid moiety has an oleic acid content of 100% and consequently a monounsaturated content of 100%.
  • the triglyceride is made up of acid moieties that are 70% oleic acid, 10% stearic acid, 5% palmitic acid, 7% linoleic and 8% hexadecenoic acid, the monounsaturated content is 78%. It is preferable that the triglyceride moieties are at least 60% oleic acid, more preferable at least 70% oleic acid and most preferable at least 80% oleic acid.
  • the viscosity modifying composition functions to decrease the slope of the viscosity temperature relationship so that the oil is more viscous at higher temperature than it would be without the viscosity improver while at the same time not making the oil too thick at lower temperatures.
  • Component
  • (B) contemplates the provision of a nitrogen-containing ester of a carboxy-containing interpolymer, said interpolymer having a reduced specific viscosity of from about 0.05 to- about 2, said ester being substantially free of titratable acidity and being characterized by the presence within its polymeric structure of at least one of each of three pendant polar groups: (A) a relatively high molecular weight carboxylic ester group having at least 8 aliphatic carbon atoms in the ester radical, (B) a relatively low molecular weight carboxylic ester group having no more than 7 aliphatic carbon atoms in the ester radical, and (C) a carbonyl-polyamino group derived from a polyamino compound having one primary or secondary amino group, wherein the molar ratio of (A) : (B) : (C) is
  • an essential element of the nitrogen-containing ester is that the ester is a mixed ester, i.e., one in which there is the combined presence of both a high molecular weight ester group and a low molecular weight ester group, particularly in the ratio as stated above.
  • Such combined presence is critical to the viscosity properties of the mixed ester, both from the standpoint of its viscosity modifying characteristics and from the standpoint of its thickening effect upon lubricating compositions in which it is used as an additive.
  • the number of carbon atoms in an ester radical is the combined total of the carbon atoms of the carbonyl group and the carbon atoms of the ester group i.e., the (OR) group.
  • Another essential element of Component (B-l) is the presence of a polyamino group derived from a particular polyamino compound, i.e., one in which there is one primary or secondary amino group and at least one mono-functional amino group.
  • a polyamino group derived from a particular polyamino compound, i.e., one in which there is one primary or secondary amino group and at least one mono-functional amino group.
  • Such polyamino groups when present in the nitrogen-containing esters of (B-l) in the proportion stated above enhances the dispersability of such esters in lubricant compositions and additive concentrates for lubricant compositions.
  • Still another essential element of Component (B-l) is the extent of esterification in relation to the extent of neutralization of the unesterified carboxy groups of the carboxy-containing interpolymer through the conversion thereof to polyamino-containing groups.
  • the relative proportions of the high molecular weight ester group to the low molecular weight ester group and to the polyamino group are expressed in terms of molar ratios of (60-90) : (10-30) : (2-15) , respectively.
  • the preferred ratio is (70-80) : (15-25) :5.
  • the linkage described as the carbonyl-polyamino group may be imide, amide, or amidine and inasmuch as any such linkage is contemplated within the present invention, the term "carbonyl polyamino" is thought to be a convenient, generic expression useful for the purpose of defining the inventive concept. In a particularly advantageous embodiment of the invention such linkage is imide or predominantly imide.
  • Component (B-l) is the molecular weight of the carboxy-containing interpolymer.
  • the molecular weight is expressed in terms of the "reduced specific viscosity" of the interpolymer which is a widely recognized means of expressing the molecular size of a polymeric substance.
  • the reduced specific viscosity (abbreviated as RSV) is the value obtained in accordance with the formula
  • the relative viscosity is determined by measur ⁇ ing, by means of a dilution visco eter, the viscosity of a solution of one gram of the interpolymer in 10 ml. of acetone and the viscosity of acetone at 30"+ 0.02*C.
  • concentration is adjusted to 0.4 gram of the interpolymer per 100 ml. of acetone.
  • interpolymers having reduced specific viscosi ⁇ ty of from about 0.05 to about 2 are contemplated in Component (B-l)
  • the preferred interpolymers are those having a reduced specific viscosity of from about 0.3 to about 1. In most instances, interpolymers having a reduced specific viscosity of from about 0.5 to about 1 are particularly preferred.
  • nitrogen-containing esters in which the high molecular weight ester group has from 8 to 24 aliphatic carbon atoms, the low molecular weight ester group has from 3 to 5 carbon atoms, and the carbonyl polyamino group is derived from a primary- a inoalkyl-substituted tertiary amine, particularly heterocyclic amines, are preferred.
  • the high molecular weight carboxylic ester group i.e., the (OR) group of the ester radical (i.e., -(0)(OR)) include heptyloxy, isooctyloxy, decyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, octadecyloxy, eicosyloxy, tricosyloxy, tetracosyloxy, etc.
  • low molecular weight groups include methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, sec- butyloxy, iso-butyloxy, n-pentyloxy, neo-pentyloxy, n-hexyloxy, cyclohexyloxy, xyxlopentyloxy, 2-methyl- butyl-1-oxy, 2,3-dimethyl-butyl-l-oxy, etc.
  • alkoxy groups of suitable size comprise the preferred high and low molecular weight ester groups. Polar substituents may be present in such ester groups.
  • Examples of polar substituents are chloro, bromo, ether, nitro, etc.
  • Examples of the carbonyl polyamino group include those derived from polyamino compounds having one primary or secondary amino group and at least one mono-functional amino group such as tertiary-amino or heterocyclic amino group.
  • Such compounds may thus be tertiary-amino substi ⁇ tuted primary or secondary amines or other substituted primary or secondary amines in which the substituent ' is derived from pyrroles, pyrrolidones, caprolactams, oxazolidones, oxazoles, thiazoles, pyrazoles, pyrazolines, imidazoles, imidazolines, thiazines, oxazines, diazines, oxycarbamyl, thiocarbamyl, uracils, hydantoins, thiohydantoins, guanidines, ureas, sulfonamides, phosphoramides, phenolthiaznes, a idines, etc.
  • Examples of such polyamino compounds include dimethylamino-ethyla ine , dibutylamino-ethylamine ,
  • 3-dimethylamino-l-propylamine 4-methylethylamino-l-butylamine, pyridyl-ethylamine, N-morpholino-ethylamine, tetrahydropyridyl-ethyiamine, bis-(dimethylamino)propyl- a ine, bis-(diethylamino)ethylamine, N,N-dimethyl-p- phenylene diamine, piperidyl-ethylamine, 1-aminoethyl pyrazole, l-(methylamino)pyrazoline, l-methyl-4-amino- octyl pyrazole, 1-aminobutyl i idazole, 4-aminoethyl thiazole, 2-aminoethyl pyridine, ortho-amino-ethyl-N,N- dimethylbenzenesulfamide, N-aminoe
  • Preferred polyamino compounds include the N-aminoalkyl-substituted morpholines such as aminopropyl morpholine.
  • the polyamino compounds are those which contain only one primary-amino or secondary-amino group and, preferably at least one tertiary-amino group.
  • the tertiary amino group is preferably a heterocyclic amino group.
  • polyamino compounds may contain up to about 6 amino groups although, in most instances, they contain one primary amino group and either one or two tertiary amino groups.
  • the polyamino compounds may be aromatic or aliphatic amines and are preferably heterocyclic amines such as amino-alkyl-substituted morpholines, piperazines, pyridines, benzopyrroles, quinolines, pyrroles, etc. They are usually amines having from 4 to about 30 carbon atoms, preferably from 4 to about 12 carbon atoms. Polar substituents may likewise be present in the polyamines.
  • the carboxy-containing interpolymers include princi ⁇ pally interpolymers of alpha, beta-unsaturated acids or anhydrides such as maleic anhydride or itaconic anhydride with olefins (aromatic or aliphatic) such as ethylene, propylene, styrene, or isobutene.
  • olefins aromatic or aliphatic
  • the styrene-maleic anhydride interpolymers are especially useful. They are obtained by polymerizing equal molar amounts of styrene and maleic anhydride, with or without one or more addi ⁇ tional interpolymerizable comonomers.
  • an aliphatic olefin may be used, such as ethylene, propylene or isobutene.
  • acrylic acid or methacrylic acid or ester thereof may be used.
  • Such interpolymers are know in the art and need not be described in detail here. Where an interpolymerizable comonomer is contemplated, it should be present in a relatively minor proportion, i.e., less that about 0.3 mole, usually less than about 0.15 mole, per mole of either the olefin (e.g. styrene) or the alpha, beta-unsaturated acid or anhydride (e.g. maleic anhydride) .
  • the interpolymerizable comonomers include the vinyl monomers such as vinyl acetate, acrylonitrile, methylacrylate, methylmethacrylate, acrylic acid, vinyl methyl either, vinyl ethyl ether, vinyl chloride, isobutene or the like.
  • the nitrogen-containing esters of Component (B-l) are most conveniently prepared by first esterifying the carboxy-containing interpolymer with a relatively high molecular weight alcohol and a relatively low molecular weight alcohol to convert at least about 50% and no more than about 98% of the carboxy radicals of the interpolymer to ester radicals and then neutralizing the remaining carboxy radicals with a polyamino compound such as described above.
  • the ratio of the high molecular weight alcohol to the low molecular weight alcohol used in the process should be within the range of from about 2:1 to about 9:1 on a molar basis. In most instances the ratio is from about 2.5:1 to about 5:1.
  • More than one high molecular weight alcohol or low molecular weight alcohol may be used in the process; so also may be used commercial alcohol mixtures such as the so-called Oxoalcohols which comprise, for example mixtures of alcohols having from 8 to about 24 carbon atoms.
  • a particularly useful class of alcohols are the commercial alcohols or alcohol mixtures comprising decylalcohol, dodecyl alcohol, tridecyl alcohol, tetradecyl alcohol, pentadecyl alcohol, hexadecyl alcohol, heptadecyl alcohol and octadecyl alcohol.
  • Other alcohols useful in the process are illustrated by those which, upon esterification, yield the ester groups exemplified above.
  • the extent of esterification may range from about 50% to about 98% conversion of the carboxy radicals of the interpolymer to ester radi ⁇ cals. In a preferred embodiment, the degree of esterification ranges from about 75% to about 95%.
  • the esterification can be accomplished simply be heating the carboxy-containing interpolymer and the alcohol or alcohols under conditions typical for effect ⁇ ing esterification.
  • Such conditions usually include, for example, a temperature of at least about 80"C, preferably from about 150°C to about 350 ⁇ C, provided that the temperature be below the decomposition point of the reaction mixture, and the removal of water of esterification as the reaction proceeds.
  • Such conditions may optionally include the use of an excess of the alcohol reactant so as to facilitate esterification, the use of a solvent or diluent such as mineral oil, toluene, benzene, xylene or the like and a esterification catalyst such as toluene sulfonic acid, sulfuric acid, aluminum chloride, boron trifluoride-triethylamine, hydrochloric acid, ammonium sulfate, phosphoric acid, sodium methoxide or the like.
  • a solvent or diluent such as mineral oil, toluene, benzene, xylene or the like
  • a esterification catalyst such as toluene sulfonic acid, sulfuric acid, aluminum chloride, boron trifluoride-triethylamine, hydrochloric acid, ammonium sulfate, phosphoric acid, sodium methoxide or the like.
  • a particularly desirable method of effecting esterification involves first reacting the carboxy-containing interpolymer with the relatively high molecular weight alcohol and then reacting the partially esterified interpolymer with the relatively low molecular weight alcohol.
  • a variation of this technique involves initiating the esterification with the relatively high molecular weight alcohol and before such esterification is complete, the relatively low molecular weight alcohol is introduced into the reaction mass so as to achieve a mixed esterification.
  • the esterified interpolymer is then treated with a polyamino compound in an amount so as to neutralize substantially all of the unesterified carboxy radicals of the interpolymer.
  • the neutralization is preferably carried out at a temperature of at least about 80°C, often from about 120 ⁇ C to about 300°C, provided that the temperature does not exceed the decomposition point of the reaction mass. In most instances the neutralization temperature is between about 150°C and 250°C.
  • a slight excess of the stoichiometric amount of the polyamino compound is often desirable, so as to insure substantial completion of neutralization, i.e., no more than about 2%
  • a styrene- aleic interpolymer is obtained by preparing a solution of styrene (16.3 parts by weight) and maleic anhydride (12.9 parts) in a benzene-toulene solution (270 parts; weight ratio of benzene:toluene being 66.5:33.5) and contacting the solution at 86'C. in nitrogen atmosphere for 8 hours with a catalyst solution prepared by dissolving 70% benzoyl peroxide (0.42 part) in a similar benzene-toulene mixture (2.7 parts).
  • the resulting product is a thick slurry of the interpolymer in the solvent mixture.
  • mineral oil 141 parts
  • the solvent mixture is being distilled off at 150'C.
  • Example fB-H-2 The procedure of Example (B-l)-l is followed except that the esterification is carried out in two steps, the first step being the esterification of the styrene-maleic interpolymer with the commercial alcohols having from 8 to 18 carbon atoms and the second step being the further esterification of the interpolymer with n-butyl alcohol.
  • Example (B-l)-l The procedure of Example (B-l)-l is followed except that the esterification is carried out by first esterifying the styrene-maleic interpolymer with the commercial alcohol having from 8 to 18 carbon atoms until 70% of the carboxyl radicals of the interpolymer have been converted to ester radicals and thereupon continuing the esterification with any yet-unreacted commercial alcohols and n-butyl alcohol until 95% of the carbonyl radicals of the interpolymer have been converted to ester radicals.
  • Example (B-l)-l The procedure of Example (B-l)-l is followed except that the interpolymer is prepared by polymerizing a solution consisting of styrene (416 parts) , maleic anhydride (392 parts) , benzene (2153 parts) and toluene (5025 parts) in the presence of benzoyl peroxide (1.2 parts) at 65"-106"C. (The resulting interpolymer has a reduced specific viscosity of 0.45).
  • Example (B-l)-5 The procedure of Example (B-l)-l is followed except that the styrene-maleic anhydride is obtained by polymerizing a mixture os styrene (416 parts) , maleic anhydride (392 parts) , benzene (6101 parts) and toluene (2310 parts) in the presence of benzoyl peroxide (1.2 parts) at 78*-92 ⁇ C. (The resulting interpolymer has a reduced specific viscosity of 0.91) .
  • Example (B-l)-l The procedure of Example (B-l)-l is followed except that the styrene-maleic anhydride is prepared by the following procedure: Maleic anhydride (392 parts) is dissolved in benzene (6870 parts) . To this mixture there is added styrene (416 parts) at 76*C. whereupon benzoyl peroxide (1.2 parts) is added. The polymerization mixture is maintained at 80-82*C. for about 5 hours. (The resulting interpolymer has a reduced specific viscosity of 1.24.)
  • EXAMPLE fB-l ⁇ -7 The procedure of Example (B-l)-l is followed except that acetone (1340 parts) is used in place of benzene as the polymerization solvent and that azobisisobutyro- nitrile (0.3 part) is used in place of benzoyl peroxide as a polymerization catalyst.
  • EXAMPLE fB-H-8 An interpolymer (0.86 carboxyl equivalent) of styrene and maleic anhydride (prepared from an equal molar mixture of styrene and maleic anhydride and having a reduced specific viscosity of 0.69) is mixed with mineral oil to form a slurry, and then esterified with a commercial alcohol mixture (0.77 mole; comprising primary alcohols having from 8 to 18 carbon atoms) at 150-160"C. in the presence of a catalytic amount of sulfuric acid until about 70% of the carboxyl radicals are converted to ester radicals.
  • a commercial alcohol mixture (0.77 mole; comprising primary alcohols having from 8 to 18 carbon atoms
  • the partially esterified interpolymer is then further esterified with a n-butyl alcohol (0.31 mole) until 95% of the carboxyl radicals of the interpolymer are converted to the mixed ester radicals.
  • the esterified interpolymer is then treated with aminopropyl morpholine (slight excess of the stoichiometric amount to neutralize the free carboxyl radicals of the interpolymer) at 150-160"C. until " the resulting product is substantially neutral (acid number of 1 to phenolphthalein indicator) .
  • the resulting product is mixed with mineral oil so as to form an oil solution containing 34% of the polymeric product.
  • Examples (B-l)-l through (B-l)-8 are prepared using mineral oil as the diluent. All of the mineral oil or a portion thereof may be replaced with a naturally occurring triglyceride.
  • the preferred triglyceride is repeseed oil or the high oleic sunflower oil.
  • Component (B) is at least one hydrocarbon-soluble acrylate polymer (Component (B-2) of the formula
  • R is a lower alkyl group containing from 1 to
  • R is a mixture of alkyl groups containing from about 4 to about 20 carbon atoms
  • x is an integer providing a weight average molecular weight
  • R is a methyl or ethyl group and more preferably, a methyl group.
  • R is primarily a mixture of alkyl groups containing from 4 to about 18 carbon atoms.
  • the weight average molecular weight of the acrylate polymer is from about 100,000 to about
  • the molecular weight of the polymer may be from 100,000 to about 700,000 and
  • alkyl groups R which may be included in the polymers of the present invention include, for example, n-butyl, octyl, decyl, dodecyl, tridecyl, octadecyl, hexadecyl, octadecyl.
  • the mixture of alkyl groups can be varied so long as the resulting polymer is hydrocarbon-soluble.
  • Acryloid 702 by R 1 ohm and Haas, wherei.n R5 i.s predominantly a mixture of n-butyl, tridecyl, and octadecyl groups.
  • Mw of the polymer is about 404,000 and the number average molecular weight (Mn) is about 118,000.
  • Another commercially available methacrylate polymer useful in the present invention is available under the tradename of "Acryloid 954" by Rohm and Haas, wherein R 5 is predominantly a mixture of n-butyl, decyl, tridecyl, octadecyl, and tetrdecyl groups.
  • the weight average molecular weight of Acryloid 954 is found to be about
  • each of these commercially available methacrylate polymers is sold in the form of a concentrate of about 40% by weight of the polymer in a light-colored mineral lubricating oil base.
  • the amount of material added is intended to represent an amount of the commercially available Acryloid material including the oil.
  • the tackifier provides adhesiveness and anti-drip characteristics to the chain bar lubricant.
  • the tackifier is a substituted succinic acylating agent which can be characterized by the presence within its structure of two groups or moieties.
  • the first group or moiety is referred to herein, for convenience, as the "substituent group(s)" and is derived from a polyalkene.
  • the polyalkene from which the substituted groups are derived is characterized by a Mn (number average molecular weight) value of from 1300 to about 5000 and a Mw/Mn value of about 1.5.to about 4.
  • succinic group(s) The second group or moiety is referred to herein as the "succinic group(s)".
  • the succinic groups are those groups characterized by the structure
  • X and/or X is usually -OH, -O-hydrocarbyl, -O— + where M+ represents one equivalent of a metal, ammonium or amine cation, -NH,, -Cl, -Br, and together, X and X can be -0- so as to form the anhydride.
  • M+ represents one equivalent of a metal, ammonium or amine cation, -NH,, -Cl, -Br, and together, X and X can be -0- so as to form the anhydride.
  • the specific identity of any X or X group which is not one of the above is not critical so long as its presence does not prevent the remaining group from entering into acylation reactions.
  • X and X are each such that both carboxyl functions of the succinic group (i.e., both
  • the substituted succinic acylating agents are characterized by the presence within their structure of at least 1.3 succinic groups (that is, groups corresponding to Formula I) for each equivalent weight of substituent groups.
  • succinic groups that is, groups corresponding to Formula I
  • the number of equivalent weights of substituent groups is deemed to be the number corresponding to the quotient obtained by dividing the Mn value of the polyalkene from which the substituent is derived into the total weight of the substituent groups present in the substituted succinic acylating agents.
  • substituted succinic acylating agents within this invention is that the substituent groups must have been derived from a polyalkene characterized by a Mw/Mn value of about 1.5 to about 4, Mw being the conventional symbol representing weight average molecular weight.
  • the Mn and Mw values for polyalkene are determined by gel permeation chroma ⁇ tography (GPC) .
  • GPC gel permeation chroma ⁇ tography
  • the Mn and Mw values of the polyalkenes of this invention can be obtained by one of ordinary skill in the art by the comparison of the distribution data obtained to a series of calibration standards of polymers of known molecular weight distribution.
  • a series of fractionated polymers of isobutene, polyisobutene being the preferred embodiment, is used as the calibration standard.
  • the Mw values disclosed herein are obtained using a Waters Associates model 200 gel permeation chromatograph equipped with a 2.5 ml syphon, a 2 ml sample injection loop and four stainless steel columns 7.8 mm in diameter by 120 centimeters long.
  • Each column was packed with ⁇ STYROGEL, a commercially available, rigid, porous gel (in particle form) of crosslinked styrene/divinyl benzene copolymers. These gels are also obtained from Waters Associates.
  • the first column contains ⁇ STYROGEL having a retention volume of 10 3 A.
  • the second and third columns contain STYROGEL having a retention size of 500 A.
  • the fourth column contains STYROGEL having a retention volume of 60 A.
  • the first column is connected to the sample loop * with stainless steel tubing, 83.3 cm long.
  • the first column is connected to the second with a 2.3 cm length of the stainless steel tubing.
  • the second and third columns are each connected by 10.2 cm lengths of tubing.
  • the fourth column is connected to the detector by a 25.4 cm length of tubing. All the connecting tubing is 1.6 mm in diameter.
  • Calibration standards were prepared by dialyzing a polyisobutylene sample having a specific gravity at 60°F.
  • sample Approximately 7 mg of sample is weighed into a small bottle which is then filled with 4 ml of reagent grade tetrahydrofuran. The sealed bottle is stored overnight before analysis.
  • the afore-described liquid phase chromatograph is degassed at 59"C. and a flow rate of 2.0 ml per minute of tetrahydrofuran maintained. Sample pressure is 180 psi and the reference pressure 175 psi.
  • the retention time of each sample is measured.
  • Polyalkenes having the Mn and Mw values discussed above are known in the art and can be prepared according to conventional procedures. Several polyalkenes, especially polybutenes, are commercially available.
  • *Rt retention time in units of number of times syphan (2.5ml) empties. The syphan empties every 2.5 min.
  • succinic groups will normally correspond to the formula
  • R and R are each independently selected from the group consisting of —OH, —Cl, —0—lower alkyl, and when taken together, R and R are —O—.
  • the succinic group is a succinic anhydride group. All the succinic groups in a particular succinic acylating agent need not be the same, but they can be the same. Preferably, the succinic groups will correspond to
  • substituted succinic acylating agents wherein the succinic groups are the same or different is within the ordinary skill of the art and can be accomplished through conventional procedures such as treating the substituted succinic acylating agents themselves (for example, hydrolyzing the anhydride to the free acid or converting the free acid to an acid chloride with thionyl chloride) and/or selecting the appropriate maleic or fumaric reactants.
  • the minimum number of succinic groups for each equivalent weight of substituent group is 1.5.
  • the minimum will be 1.4; usually 1.4 to about 3.5 succinic groups for each equivalent weight of substituent group.
  • a preferred range based on this minimum is at least 1.5 to about 2.5 succinic groups per equivalent weight of substituent groups.
  • substituted succinic acylating agents of this invention can be represented by the symbol -R 2 )
  • R 1 represents one equivalent weight of substituent group
  • R_ represents one succinic group corresponding to Formula I, Formula II, or Formula III ' as discussed above
  • y is a number equal to or greater than 1.3; ie., >1.3.
  • the more preferred embodiments of the invention could be similarly represented by, for example, letting R.
  • R_ represent more preferred substituent groups and succinic groups, respectively, as discussed elsewhere herein and by letting the value of y vary as discussed above; eg., y is equal to or greater than 1.4 (y 1.4; y is equal to or greater than 1.5 (y>1.5) ; y equals 1.4 to about 3.5 (y>.1.4-3.5) ; and y equals 1.5 to about 3.5 (y .1.5-3.5) .
  • Mn for example, a minimum of about 1500 is preferred with an Mn value in the range of from about 1500 to about 3200 also being preferred. A more preferred Mn value is one in the range of from about 1500 to about 2800. A most preferred range of Mn values is from about 1500 to about 2400. With polybutenes, an especially preferred minimum value for Mn is about 1700 and especially preferred range of Mn values is from about 1700 to about 2400.
  • a minimum Mw/Mn value of about 1.8 is preferred with a range of values of about 1.8 up to about 3.6 also being preferred.
  • a still more preferred minimum value of Mw/Mn is about 2.0 with a preferred range of values of from about 2.0 to about 3.4 also being a preferred range.
  • An especially preferred minimum value of Mw/Mn is about 2.5 with a range of values of about 2.5 to about 3.2 also being especially preferred.
  • the polyalkenes from which the substituent groups are derived are homopoly ers and interpolymers of polymerizable olefin monomers of 2 to about 16 carbon atoms; usually 2 to about 6 carbon atoms.
  • the interpolymers are those in which two or more olefin monomers are interpolymerized according to well-known conventional procedures to form polyalkenes having units within their structure derived from each of said two or more olefin monomers.
  • "interpolymer(s)" as used herein is inclusive of copolymers, terpolymers, tetrapolymers, and the like.
  • the polyalkenes from which the substituent groups are derived are often conventionally referred to as "polyolefin(s)".
  • polymerizable internal olefin monomers (sometimes referred to in the patent literature as medial olefins) characterized by the presence within their structure of the group
  • polyalkenes can also be used to form the polyalkenes.
  • internal olefin monomers When internal olefin monomers are employed, they normally will be employed with terminal olefins to produce polyalkenes which are interpolymers.
  • terminal olefins For purposes of this invention, when a particular polymerized olefin monomer can be classified as both a terminal olefin and an internal olefin, it will be deemed to be a terminal olefin.
  • pentadiene-1,3 i.e., piperylene
  • polyalkenes from which the substituent groups of the succinic acylating agents are derived generally are hydrocarbon polyalkenes, they can contain non-hydrocarbon polyalkenes, they can contain non-hydrocarbon groups such as lower alkoxy, lower alkyl mercapto, hydroxy, mercapto, oxo (i.e. ,
  • keto and aldehydo groups as in keto and aldehydo groups; e.g.
  • alkyl is usually lower alkly alkanoyloxy (i.e., alkyl)
  • alkyl is usually lower alkyl, and the like provided the non-hydrocarbon substituents do not substantially interfere with formation of the substituted succinic acid acylating agents of this invention.
  • non-hydrocarbon groups normally will not contribute more than about 10% by weight of the total weight of the polyalkenes. Since the polyalkene can contain such non-hydrocarbon substituent, it is apparent that the olefin monomers from which the polyalkenes are made can also contain such substituents. Normally, however, as a matter of practicality and expense, the olefin monomers and the polyalkenes will be free from non-hydrocarbon groups, except chloro groups which usually facilitate the formation of the substituted succinic acylating agents of this invention. (As used herein, the term "lower” when used with a chemical group such as in "lower alkyl” or lower alkoxy" is intended to describe groups having up to seven carbon atoms.)
  • the polyalkenes may include aromatic groups (especially phenyl groups and lower alkyl-and/or lower alkoxy-substituted phenyl groups such as para-(tert-butyl)phenyl) and cycloaliphatic groups such as would be obtained from polymerizable acyclic olefins, the polyalkenes usually will be free from such groups. Nevertheless, polyalkenes derived from interpolymers of both 1,3-dienes and styrenes such as butadiene-1,3 and styrene or para-(tert-butyl)styrene are exceptions to this generalization. Again, because aromatic and cycloaliphatic groups can be present, the olefin monomers from which the polyalkenes are prepared can contain aromatic and cycloaliphatic groups.
  • polyalkene there is a general preference for aliphatic, hydrocarbon polyalkenes free from aromatic and cycloaliphatic groups (other than the dienestyrene interpolymer exception already noted) .
  • polyalkenes which are derived from the group consisting of homopolymers and interpolymers of terminal hydrocarbon olefins of 2 to about 16 carbon atoms.
  • interpolymers of terminal olefins are usually preferred, interpolymers optionally containing up to about 40% of polymer units derived from internal olefins of up to about 16 carbon atoms are also within a preferred group.
  • a more preferred class of polyalkenes are those selected from the group consisting of homopolymers and interpolymers of terminal olefins of 2 to about 6 carbon atoms, more preferably 2 to 4 carbon atoms.
  • another preferred class of polyalkenes are the latter more preferred polyalkenes optionally containing up to about 25% of polymer units derived from internal olefins of up to about 6 carbon atoms.
  • terminal and internal olefin monomers which can be used to prepare the polyalkenes according to conventional, well-known polymerization techniques include ethylene; propylene; butene-1; butene-2; isobutene; pentene-1; hexene-1; heptene-1; octene-1; nonene-1; decene-l; pentene-2; propylene-tetramer; diisobutylene; isobutylenetrimer; butadiene-1-2, ; butadiene-1,3; pentadiene-1,2; pentadiene-1,3; pentadiene-1,4; isoprene; hexadiene-1,5; 2-chloro-butadiene-l,3; 2-methyl-heptene-1;
  • polyalkenes include polypropylenes, polybutenes, ethylene-propylene copolymers, styrene-isobutene copolymers, isobutene- butadiene-1,3 copolymers, propene-isoprene copolymers, isobutene-(para-methyl)styrene copolymers, copolymers of hexene-1 with hexadiene-1,3, copolymers of octene-1 with hexene-1, copolymers of heptene-1 with pentene-l, copolymers of 3-methyl-butene-1 with octene-1, copolymers of 3,3-dimethyl-pentene-l with hexene-l, and terpolymers of isobutene, styrene and piperylene.
  • interpolymers include copolymer of 95% (by weight) of isobutene with 5% (by weight) of styrene; terpolymer of 98% of isobutene with 1% of piperylene and 1% of chloroprene; terpolymer of 95% of isobutene with 2% of butene-1 and 3% of hexene-1; terpolymer of 60% of isobutene with 20% of pentene-1 and 20% of octene-1; copolymer of 80% of hexene-1 and 20% of heptene-1; terpolymer of 90% of isobutene with 2% of cyclohexene and 8% of propylene; and copolymer of 80% of ethylene and 20% of propylene.
  • a preferred source of polyalkenes are the poly(isobutene)s obtained by polymerization of C 4 refinery stream having a butene content of about 35 to about 75 percent by weight and an isobutene content of about 30 to about 60 percent by weight in the presence of a Lewis acid catalyst such as aluminum trichloride or boron trifluoride. These polybutenes contain predominantly (greater than about 80% of the total repeating units) isobutene repeating units of the configuration
  • polyalkenes as described above which meet the various criteria for Mn and Mw/Mn is within the skill of the art and does not comprise part of the present invention.
  • Techniques readily apparent to those in the art include controlling polymerization temperatures, regulating the amount and type of polymerization initiator and/or catalyst, employing chain terminating groups in the polymerization procedure, and the like.
  • Other conventional techniques such as stripping (including vacuum sripping) a very light end and/or oxidatively or mechically degrading high molecular weight polyalkene to produce lower molecular weight polyalkenes can also be used.
  • one or more of the above-described polyalkenes is reacted with one or more acidic reactants selected from the group consisting of maleic or fumaric reactants of the general formula
  • maleic and fumaric reactants will be one or more compounds corresponding to the formula
  • the maleic or fumaric reactants will be maleic acid, fumaric acid, maleic anhydride, or a mixture of two or more of these.
  • the maleic reactants are usually preferred over the fumaric reactants because the former are more readily available and are, in general, more readily reacted with the polyalkenes (or derivatives thereof) to prepare the substituted succinic acylating agents of the present invention.
  • the especially preferred reactants are maleic acid, maleic anhydride, and mixtures of these. Due to availability and ease of reaction, maleic anhydride will usually be employed.
  • the one or more polyalkenes and one or more maleic or fumaric reactants can be reacted according to any of several known procedures in order to produce the substituted succinic acylating agents of the present invention.
  • the procedures are analogous to procedures used to prepare the high molecular weight succinic anhydrides and other equivalent succinic acylating analogs thereof except that the polyalkenes (or polyolefins) of the prior art are replaced with the particular polyalkenes described above and the amount of maleic or fumaric reactant used must be such that there is at least 1.3 succinic groups for each equivalent weight of the substituent group in the final substituted succinic acylating agent produced.
  • maleic reactant is often used hereafter. When used, it should be understood that the term is generic to acidic reactants selected from maleic and fumaric reactants corresponding to Formulas IV and V above including * a mixture of such reactants.
  • the molecular weight of the polyalkene is the weight corresponding to the Mn value.
  • Chlorination involves merely contacting the polyalkene with chlorine gas until the desired amount of chlorine is incorporated into the chlorinated polyalkene.
  • Chlorination is generally carried out at a temperature of about 75"C to about 125*C. If a diluent is used in the chlorination procedure, it should be one which is not itself readily subject to further chlorination. Poly- and perchlorinated and/or flurorinated alkanes and benzenes are examples of suitable diluents.
  • the second step in the two-step chlorination procedure is to react the chlorinated polyalkene with the maleic reactant at a temperature usually within the range of about 100*C to about 200"C.
  • the mole ratio of chlorinated polyalkene to maleic reactant is usually about 1:1.
  • a mole of chlorinated polyalkene is that weight of chlorinated polyalkene corresponding to the Mn value of the unchlorinated polyalkene.
  • a stoichiometric excess of maleic reactant can be used, for example, a mole ratio of 1:2.
  • an equivalent weight of chlorinated polyalkene is the weight corresponding to the Mn value divided by the average number of chloro groups per molecule of chlorinated polyalkene while the equivalent weight of a maleic reactant is its molecular weight.
  • the ratio of chlorinated polyalkene to maleic reactant will normally be such as to provide about one equivalent of maleic reactant for each mole of chlorinated polyalkene up to about one equivalent of maleic reactant for each equivalent of chlorinated polyalkene with the understanding that it is normally desirable to provide an excess of maleic reactant; for example, an excess of about 5% to about 25% by weight. Unreacted excess maleic reactant may be stripped from the reaction product, us . ly under vacuum, or reacted during a further stage of the process as explained below.
  • the resulting polyalkenyl-substituted succinic acylating agent is, optionally, again chlorinated if the desired number of succinic groups are not present in the product. If there is present, at the time of this subsequent chlorination, any excess maleic reactant from the second step, the excess will react as additional chlorine is introduced during the subsequent chlorination. Otherwise, additional maleic reactant is introduced during and/or subsequent to the additional chlorination step. This technique can be repeated until the total number of succinic groups per equivalent weight of substituent groups reaches the desired level.
  • Another procedure for preparing substituted succinic acid acylating agents of the invention utilizes a process described in U.S. Pat. No. 3,912,764 and U.K. Pat No.
  • 1,440,219 both of which are expressly incorporated herein by reference for their teachings in regard to that process.
  • the polyalkene and the maleic reactant are first reacted by heating them together in a "direct alkylation" procedure.
  • chlorine is introduced into the reaction mixture to promote reaction of the remaining unreacted maleic reactants.
  • 0.3 to 2 or more moles of maleic anhydride are used in the reaction for each mole of olefin polymer, ie. , polyalkene.
  • the direct alkylation step is conducted at temperatures of 180*C to 250 * C.
  • a temperature of 160 # C. to 225*C. is employed.
  • the one-step process involves preparing a mixture of the polyalkene and the maleic reactant containing the necessary amounts of both to provide the desired substituted succinic acylating agents of this invention. This means that there must be at least 1.3 moles of maleic reactant for each mole of polyalkene in order that there can be at least 1.3 succinic groups for each equivalent weight of substituent groups. Chlorine is then introduced into the mixture, usually by passing chlorine gas through the mixture with agitation, while maintaining a temperature of at least about 140 ⁇ C.
  • the polyalkene is sufficiently fluid at 140°C. and above, there is no need to utilize an additional substantially inert, normally liquid solvent/diluent in the one-step process.
  • a solvent/diluent it is preferably one that resists chlorination.
  • Chlorine may be introduced continuously or intermittently during the one-step process. The rate of introduction of the chlorine is not critical although, for maximum utilization of the chlorine, the rate should be about the same as the rate of consumption of chlorine in the course of the reaction. When the introduction rate of chlorine exceeds the rate of consumption, chlorine is evolved from the reaction mixture. It is often advantageous to use a closed system, including superatmospheric pressure, in order to prevent loss of chlorine so as to maximize chlorine utilization.
  • the minimum temperature at which the reaction in the one-step process takes place at a reasonable rate is about 140"C.
  • the preferred temperature range is usually between about 160"C. and about 220*C. Higher temperatures such as 250'C. or even higher may be used but usually with little advantage. In fact, temperatures in excess of 220'C. are often disadvantageous with respect to preparing the particular acylated succinic compositions of this invention because they tend to crack the polyalkenes (that is, reduce their molecular weight by thermal degradation) and/or decompose the maleic reactant. For this reason, maximum temperatures of about 200° to about 210"C. are normally not exceeded.
  • the upper limit of the useful temperature in the one-step process is determined primarily by the decomposition point of the components in the reaction mixture including the reactants and the desired products.
  • the decomposition point is that temperature at which there is sufficient decomposition of any reactant or product such as to interfere with the production of the desired products.
  • the molar ratio of maleic reactant to chlorine is such that there is at least about one mole of chlorine for each mole of maleic reactant to be incorporated into the product. Moreover, for practical reasons, a slight excess, usually in the neighborhood of about 5% to about 30% by weight of chlorine, is utilized in order to offset any loss of chlorine from the reaction mixture. Larger amounts of excess chlorine may be used but do not appear to produce any beneficial results.
  • the molar ratio of polyalkene to maleic reactant is such that there is at least about 1.3 moles of maleic reactant for each mole of polyalkene. This is necessary in order that there can be at least 1.3 succinic groups per equivalent weight of substituent group in the product. Preferably, however, an excess of maleic reactant is used. Thus, ordinarily about a 5% to about 25% excess of maleic reactant will be used relative to that amount necessary to provide the desired number of succinic groups in the product.
  • a preferred process for preparing the substituted acylating compositions of this invention comprises heating and contacting at a temperature of at least about 140°C up to the decomposition temperature
  • a direct alkylation reaction can precede the introduction of chlorine.
  • the original reaction mixture will contain the total amount of polyalkene and acidic reactant to be utilized.
  • the amount of chlorine used will normally be such as to provide about one mole of chlorine for each unreacted mole of (B) present at the time chlorine introduction is commenced.
  • the amount of chlorine introduced to complete reaction will be based on the unreacted 0.75 mole of (B) ; that is, at least about 0.75 mole of chlorine (or an excess as explained above) will then be introduced.
  • (C) Chlorine wherein the mole ratio of (A) : (B) is such that here is at least about 1.3 moles of (B) for each mole of (A) where the number of moles of (A) is a quotient of the total weight of (A) divided by the value of Mn, and the amount of chlorine employed is such as to provide at least about one mole of chlorine for each mole of (B) reacted with (A) , the substituted acylating compositions being further characterized by the presence within their structure of at least 1.3 groups derived from (B) for each equivalent weight of the substituent groups derived from (A) .
  • This process includes only the one-step process; that is, a process where all of both (A) and (B) are present in the initial reaction mixture.
  • the substituted acylated composition as produced by such a process are, likewise, part of this invention.
  • substituted succinic acylating agent(s) and "substituted acylating composition” as used herein.
  • the former terminology is used in describing the the substituted succinic acylating agents regardless of the process by which they are produced.
  • the latter terminology that is, “substituted acylating composition(s) , is used to describe the reaction mixtures produced by the specific preferred processes described in detail herein.
  • identity of particular substituted acylating compositions is dependent upon a particular process of manufacture.
  • reaction temperature is from about 160*C. to about 220*C.
  • polyalkenes wherein the polyalkene is a homopoly er or interpolymer of terminal olefins of 2 to about 16 carbon atoms, with the proviso that said interpolymers can optionally contain up to about 40% of the polymer units derived from internal olefins of up to about sixteen carbon atoms, constitutes the preferred aspect of the process and compositions prepared by the process.
  • polyalkenes for use in the process and in preparing the compositions of the process are the homopolymers and interpolymers of terminal olefins of 2 to 6 carbon atoms with the proviso that said interpolymers can optionally contain up to about 25% of polymer units derived from internal olefins of up to about 6 carbon atoms.
  • Especially preferred polyalkenes are polybutenes, ethylene-propylene copolymers, polypropylenes with the poly-butenes being particularly preferred.
  • the succinic group content of the substituted acylating compositions thus produced are preferably the same as that described in regard to the substituted succinic acylating agents.
  • the substituted acylating compositions characterized by the presence within their structure of an average of at least
  • succinic groups derived from (B) for each equivalent weight of the substituent groups derived from (A) are preferred with those containing at least 1.4 up to about
  • succinic groups derived from (B) for each equivalent weight of substituent groups derived from (A) being still more preferred.
  • those substituted acylating compositions characterized by the presence within their structure of at least 1.5 succinic groups derived from (B) for each equivalent weight of substituent group derived from (A) are still further preferred, while those containing at least 1.5 succinic groups derived from (B) for each equivalent weight of substituent group derived from (A) being especially preferred.
  • An especially preferred process for preparing the substituted acylating compositions comprises heating at a temperature of about 160 ⁇ C to about 220'C. a mixture comprising:
  • the reaction mixture is held at 200°-224°c for 6.33 hours, stripped at 210"C. under vacuum and filtered.
  • the filtrate is the desired polyisobutene-substituted succinic acylating agent having a saponification equivalent number of 94 as determined by ASTM procedure D-94.
  • EXAMPLE C-6 A mixture of 800 parts of a polyisobutene falling within the scope of the claims of the present invention and having a Mn of about 2000, 646 parts of mineral oil and 87 parts of maleic anhydride is heated to 149'C. in 2.3 hours. At 176"-180°C. 100 parts of gaseous chlorine is added beneath the surface over a 19 hour period. The reaction mixture is stripped by blowing with nitrogen for 0.5 hour at 180°C. The residue is an oil-containing solution of the desired polyisobutene-substituted succinic acylating agent.
  • the pour point depressant functions by acting as a nucleating agent which promotes the formation of small wax crystals; the PPD does not prevent wax crystal formation. Controlling the volume of the crystal is key in maintaining lubricant flow.
  • the PPD is similar to the viscosity modifying composition in all respects except that the carboxy containing interpolymer has a reduced specific viscosity of from about 0.05 to about 1 and being characterized by the presence within its polymeric structure of at least one of each of the following groups which are derived from the carboxy groups of said interpolymer:
  • (B') a carbonyl-polyamino group derived from a poly ⁇ amino compound having one primary or secondary amino group and at least one mono-functional amino group, wherein the molar ration of carboxy groups of said interpolymer esterified to provide (A') to carboxy groups of said interpolymer neutralized to provide (B') is in the range of about 85:15 to about 99:1.
  • the (A ) (C-2) is the same as the (A) of (C-l) and the (B') of (C-2) is the same as the (C) of (C-l).
  • the following examples are illustrative of the preparation of (C-2) of the present invention. Unless otherwise indicated all parts and percentages are by weight.
  • a styrene-maleic interpolymer is obtained by preparing a solution of styrene (536 parts) and maleic anhydride (505 parts) in toluene (7585 parts) and contacting the solution at a temperature of 99-101*C and an absolute pressure of 480-535 mm. Hg. with a catalyst solution prepared by dissolving benzoyl peroxide (2.13 parts) in toluene (51.6 parts). The catalyst solution is added over a period of 1.5 hours with the temperature maintained at 99-101*C. Mineral oil (2496 parts) is added to the mixture. The mixture is maintained at 99-101'C and 480-535 mm Hg for 4 hours. The resulting product is a slurry of the interpolymer in the solvent mixture. The resulting interpolymer has a reduced specific viscosity of 0.42.
  • EXAMPLE D-2 A toluene slurry (2507 parts), having 11.06% solids and 88.94% volatiles, of the maleic anhydride/styrene interpolymer of Example D-l, Neodol 45 (632 parts) , a product of Shell Chemical Company identified as a mixture of C14 and C15 liner primary alcohols, mineral oil (750 parts), and Ethyl Antioxidant 733 (4.2 parts), a product of Ethyl identified as an isomeric mixture of butyl phenols, are charged to a vessel. The mixture is heated with medium agitation under nitrogen purge at 0.5 standard cubic feet per hour until the temperature reaches 115*C.
  • the mixture is maintained at 150°C for an additional 30 minutes, then cooled with stirring. " The mixture is stripped from 50°C to 141'C at a pressure of 102 mm. Hg then permitted to cool. At a temperature of 100'C, mineral oil (617 parts) is added. Cooling is continued to 60°C. At 60°C, diatomaceous earth (36 parts) is added and the mixture is heated to 100"C. The mixture is maintained at 100-105°C for one hour with stirring and then filtered to yield the desired product.
  • EXAMPLE D-4 A toluene slurry (1125 parts), having 13.46% solids and 86.54% volatiles, of the maleic anhydride/styrene interpolymer of Example D-l, mineral oil (250 parts) and Neodol 45 (344 parts) are charged to a vessel. The mixture is heated with medium agitation under nitrogen sweep of 0.5 standard cubic feet per hour until the temperature reaches 110°C. Paratoluene sulfonic acid (8.55 parts) in water (9 parts) is added dropwise over a period of 24 minutes. The temperature of the mixture is increased to 152°C. by removing toluene-water distillate.
  • EXAMPLE D-5 The procedure of Example D-4 is repeated with the exception that both Neodol 45 (172 parts) and Alfol 1218 (169 parts) are provided in the initial charge, rather than the 344 parts of Neodol 45 provided in Example D-4.
  • EXAMPLE D-6 The product of Example D-l (101 parts) , Neodol 91 (56 parts) a product of Shell Chemical Company identified as a mixture of C9, CIO, and Cll alcohols, TA-1618 (92 parts) , a product of Procter & Gamble identified as a mixture of C16 and C18 alcohols, Neodol 25 (62 parts), a product Shell Chemical Company identified as a mixture of C12, C13, C14, and C15 alcohols, and toluene (437 parts) are charged to a vessel. The vessel is stirred and the contents are heated. Methane sulfonic acid (5 parts) is added to the mixture. The mixture is heated under reflux conditions for 30 hours.
  • Aminopropylmorpholine (12.91 parts) is added to the mixture. The mixture is heated under reflux conditions for an additional 4 hours. Diatomaceous earth (30 parts) and a neutral paraffinic oil (302 parts) are added to the mixture which is then stripped. The residue is filtered to yield 497.4 parts of an orange-brown viscous liquid.
  • Example D-l The product of Example D-l (202 parts) , Neodol 91 (112 parts), TA 1618 (184 parts), Neodol 25 (124 parts and toluene (875 parts) are charged to a vessel. The mixture is heated and stirred. Methane sulfonic aci ' d (10 parts) is added to the mixture which is then heated under reflux conditions for 31 hours. Aminopropylmorpholine (27.91 parts) is added to the mixture which is then heated under reflux conditions for an additional 5 hours. Diatomaceous earth (60 parts) is added to the mixture which is then stripped and 600 parts of polymer remain in the vessel. A neutral paraffinic oil (600 parts) is added to the mixture which is then homogenized. The mixture is filtered through a heated funnel to yield 1063 parts of a clear orange-brown viscous liquid.
  • Example D-l 101 parts
  • Alfol 810 50 parts
  • a product of Continental Oil Company identified as a mixture of C8 and CIO alcohols TA-1618 (92 parts)
  • Neodol 25 62 parts
  • toluene 437 parts
  • Methane sulfonic acid 5 parts
  • Aminopropylmorpholine (15.6 parts) is added to the mixture which is then heated under reflux conditions for an additional 5 hours.
  • the mixture is stripped to yield 304 parts of a yellow-orange viscous liquid.
  • Diatomaceous earth (30 parts) and a neutral paraffinic oil (304 parts) are added to the mixture which is then homogenized.
  • the mixture is filtered through a heated funnel to yield 511 parts of a clear amber viscous liquid.
  • a toluene slurry (799 parts) of a maleic ' anhydride/styrene interpolymer (17.82% polymer) is charged to a vessel.
  • the reduced specific viscosity of the interpolymer is 0.69.
  • the vessel is purged with nitrogen while stirring the contents for 15 minutes.
  • Alfol 1218 (153 parts) , Neodol 45 (156 parts) and 93% sulfuric acid (5 parts) are added to the mixture.
  • Toluene (125 parts) is then added to the mixture.
  • the mixture is heated at 150-156"C. for 18 hours.
  • Aminopropylmorpholine 1.3 parts is added to the mixture which is then heated for an additional 1 hour at 150 * C.
  • the mixture is cooled to 80 'C.
  • Ethyl Antioxidant 733 (1.84 parts) is added to the mixture. The mixture is stripped at 143"C. and 100 mm. Hg. Mineral oil (302 parts) and Ethyl Antioxidant 733 (2.5 parts) is added to the mixture while the mixture is stirred. Diatomaceous earth (25 parts) is added to the mixture. The temperature of the mixture is maintained at 70*C. for 45 minutes and then heated to 110"C. Diatomaceous earth (25 parts) is added to the mixture. The mixture is filtered through diatomaceous earth to yield the desired product.
  • Neodol A toluene and mineral oil slurry (699 parts) containing 17.28% solids of a maleic anhydride/styrene interpolymer (reduced specific viscosity of 0.69), Neodol
  • the antiwear agent provides a sacrifical film on the metal surface. This film is then removed during asperity contact thereby reducing the removal of metal from the surface.
  • the antiwear agent is a sulfurized composition (E-l) .
  • Useful sulfurized compositions for use in connection with the present invention are prepared by reacting, at about 100°-250°C. , sulfur with a mixture comprising (A) 100 parts by weight of at . * *.ast or-, fatty acid ester, (B) about 0-50 parts by weig ⁇ t of a-, least one fatty acid, and (C) about 25-400 parts by weJ ght of at least one aliphatic olefin containing about 8-36 carbon atoms.
  • Reagent A is at least one fatty acid ester.
  • fatty acid refers to acids which may be obtained by hydrolysis of a naturally occurring vegetable or animal fat or oil. These are usually in the C 16 - 20 ran ⁇ ? e and include palmitic acid, stearic acid oleic acid, linoleic acid and the like.
  • Fatty acid esters which are useful as reagent A are primarily those with aliphatic alcohols, including monohydric alcohols such as methanol, ethanol, n-propanol, isopropanol, the butanols, etc., and polyhydric alcohols including ethylene glycol, propylene glycol, trimethylene glycol, neopentyl glycol, glycerol and the like.
  • Particularly preferred are the fatty oils, that is, naturally occurring esters of glycerol with the above noted long chain carboxylic acids, and synthetic esters of similar structure.
  • Still more preferred are fatty oils derived from unsaturated acids, especially oleic and linoleic, including such naturally occurring animal and vegetable oils as lard oil, peanut oil, cottonseed oil, soybean oil, corn oil, sunflower oil and the like.
  • Reagent B is at least one fatty acid as described above. It is usually an unsaturated fatty acid such as oleic or linoleic acid, and may be a mixture of acids such as is obtained from tall oil or by the hydrolysis of peanut oil, soybean oil or the like.
  • the amount of reagent B is about 0-50 parts by weight per 100 parts of reagent A; that is, it is an optional ingredient. However, it improves the slip, rust inhibiting and extreme pressure properties of lubricants containing the sulfurized compositions of this invention, and so its presence (generally in the amount of about 2-8 parts by weight is preferred.
  • Reagent C is at least one C 8 _ 36 aliphatic olefin. About 25-400 parts, usually about 25-75 parts, of reagent C are present per 100 parts of reagent A. Terminal olefins, or alpha-olefins, are preferred, especially those in C_ 2 _ 20 range. Mixtures of these olefins are commercially available and such mixtures are contemplated for use in this invention.
  • the reaction mixture may contain other materials. These may include, for example, sulfurization promoters, typically phosphorous-containing reagents such as phosphorous acid esters (e.g. , triphenyl phosphite) , and surface active agents such as lecithin.
  • sulfurization promoters typically phosphorous-containing reagents such as phosphorous acid esters (e.g. , triphenyl phosphite)
  • surface active agents such as lecithin.
  • the sulfurization occurs at a temperature of about 100 ⁇ -250 ⁇ C, usually about 150 ⁇ -210'C.
  • the weight ratio of the combination of reagents A, B and C to sulfur is between about 5:1 and 15:1, generally between about 5:1 and 10:1.
  • the sulfurization reaction is effected by merely heating the reagents at the temperature indicated above, usually with efficient agitation and in an inert atmosphere (e.g., nitrogen). If any of the reagents, especially reagent C, are appreciably volatile at the reaction temperature, the reaction vessel may be sealed and maintained under pressure. It is frequently advantageous to add the sulfur portionwise to the mixture of the other reagents. While it is usually preferred that the reaction mixture consist entirely of the reagents previously described, the reaction may also be effected in the presence of an inert solvent (e.g., an alcohol, ether, ester, aliphatic hydrocarbon, halogenated aromatic hydrocarbon or the like) which is liquid within the temperature range employed.
  • an inert solvent e.g., an alcohol, ether, ester, aliphatic hydrocarbon, halogenated aromatic hydrocarbon or the like
  • reaction temperature is relatively high, e.g., about 200 ⁇ C
  • a lower reaction temperature e.g., about 150 ⁇ -170°C.
  • the reaction sometimes requires a longer time at lower temperatures and an adequate sulfur content is usually obtained when the temperature is at the high end of the recited range.
  • insoluble by-products may be removed by filtration, usually at an elevated temperature (about 80°-120°C).
  • the filtrate is the desired sulfurized product.
  • a mixture of 60 parts of commercial c ⁇ 5-20 alpha-olefins and 100 parts of lard oil is heated to 160*C., under nitrogen, and 12 parts of sulfur is added.
  • the mixture is heated at 65*-200'C. and an additional 6.5 parts of sulfur is added. Heating is continued for 4 hours, after which the mixture is cooled to 100 ⁇ C. and filtered to yield the desired product which contains 9.0% sulfur.
  • a mixture of 100 parts of soybean oil and 50 parts of commercial C. g alpha-olefins is heated to 175°C. under nitrogen and 17.4 parts of sulfur is added gradually, whereupon an exothermic reaction causes the temperature to rise to 205"C.
  • the mixture is heated at 188*-220"C. for 5 hours, allowed to cool gradually to 90 ⁇ C. and filtered to yield the desired product containing 10.13% sulfur.
  • EXAMPLE (E-D-10 A mixture of 100 parts of soybean oil, 3.7 parts of tall oil acid and 46.3 parts of commercial C. 15_—l.o_ alpha-olefins is heated to 165°C. under nitrogen, and 17.4 parts of sulfur is added. The temperature of the mixture rises to 191"C. It is maintained at 165 o -200°C. for 7 hours and is then cooled to 90°C. and filtered. The product contains 10.13% sulfur.
  • Component (E) as (E-2) is a composition combining the mixture of from about 85-98, preferably 93-98 parts by weight of a salt of the formula
  • R and R are independently substantially hydrocarbyl groups containing from about 3 to about 20 carbon atoms, with from about 2-15, preferably 2-7 parts by weight of an anhydride of the formula
  • the substantially saturated R and R radicals preferably contain from about 3 to about 10 carbon atoms and may be alkyl and alkylphenyl groups.
  • Illustrative alkyl radicals include isopropyl, isobutyl, n-butyl, sec-butyl, the isomeric amyl radicals, the isomeric hexyl radicals, the isomeric heptyl radicals and the isomeric octyl radicals.
  • a preferred alkyl radical is
  • Illustrative alkylphenyl radicals include butylphenyl, amylphenyl, diamylphenyl, octyl-phenyl, etc.
  • Other substantially hydrocarbon radicals are useful such as tetradecyl, octadecyl, eicosyl, butylnaphthyl, hexylnaphthyl, octylnaphthyl, naphthenyl, etc.
  • the preparation of the zinc salt is known in the art. Specifically it is prepared by the reaction of phosphorus pentasulfide with an alcohol or phenol. The reaction involves four moles of the alcohol or phenol per mole of phosphorus pentasulfide, and may be carried out within the temperature range from about 50°C to about 200°C.
  • the preparation of 0,0-di-n-hexyl phosphorodithioic acid involves the reaction of phosphrous pentasulfide with four moles of n-hexyl alcohol at about 100°C for about two hours. Hydrogen sulfide is liberated and the residue is an acid.
  • the preparation of the zinc salt of this acid may be effected by reaction with zinc oxide. Simply mixing and heating two moles of the phosphorodithioic acid and one mole of zinc oxide is sufficient to cause the reaction to take place and the resulting product is sufficiently pure for the purposes of this invention.
  • Especially useful zinc phosphorodithioates can " be prepared from phosphorodithioic acids which in turn are prepared by the reaction of phosphorus pentasulfide with mixtures of alcohols.
  • the use of such mixtures enables the utilization of cheaper alcohols which in themselves do not yield oil-soluble phosphorodithioic acids.
  • a mixture of isopropyl and hexyl alcohols can be used to produce a very effective, oil-soluble zinc-phosphoro- dithiothate.
  • R of the anhydride is illustrated by the isomeric butyls, isomeric pentyls, isomeric hexyls, isomeric heptyls, isomeric octyls, isomeric nonyls, isomeric decyls, etc.
  • the preparation of this anhydride is known in the art and involves reacting maleic anhydride with an olefin polymer or a chlorinated substantially saturated hydrocarbon.
  • the anhydride is prepared by reacting polypropylene tetramer with maleic anhydride.
  • the anhydride is reacted with water and an alkylene oxide comprising ethylene oxide, propylene oxide, 1,2-butene oxide, trimethylene oxide, tetramethylene oxide, butadiene monoepoxide and 1,2-hexene oxide.
  • an alkylene oxide comprising ethylene oxide, propylene oxide, 1,2-butene oxide, trimethylene oxide, tetramethylene oxide, butadiene monoepoxide and 1,2-hexene oxide.
  • propylene oxide For every 1000 parts anhydride about 50-80 parts alkylene oxide and 90-120 parts water is employed.
  • composition of the present invention comprising components (A) , (B) , (C) ; (A) , (B) , (C) and (D) ; (A) , (B) , (C) and (E) ; or (A) , (B) , (C) , (D) and (E) is useful as a chain bar lubricant.
  • Component (B) as Acryloid 954 7.00 7.00

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Materials For Medical Uses (AREA)
EP92921368A 1991-10-31 1992-10-08 A biodegradable chain bar lubricant Ceased EP0565661A1 (en)

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US78563991A 1991-10-31 1991-10-31
US785639 1991-10-31

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US5413725A (en) * 1992-12-18 1995-05-09 The Lubrizol Corporation Pour point depressants for high monounsaturated vegetable oils and for high monounsaturated vegetable oils/biodegradable base and fluid mixtures
US5399275A (en) * 1992-12-18 1995-03-21 The Lubrizol Corporation Environmentally friendly viscosity index improving compositions
US5338471A (en) * 1993-10-15 1994-08-16 The Lubrizol Corporation Pour point depressants for industrial lubricants containing mixtures of fatty acid esters and vegetable oils
US6156228A (en) * 1994-11-16 2000-12-05 Houghton International, Inc. Trialkoxyalkylphosphate-based fire resistant fluid containing triglyceride
DE4444137A1 (de) * 1994-12-12 1996-06-13 Henkel Kgaa Synthetische Ester aus Alkoholen und Fettsäuregemischen aus ölsäurereichen, stearinsäurearmen Pflanzenölen
US5658864A (en) * 1995-03-24 1997-08-19 Ethyl Corporation Biodegradable pour point depressants for industrial fluids derived from biodegradable base oils
US5707943A (en) * 1996-12-16 1998-01-13 The Lubrizol Corporation Mixtures of esterified carboxy-containing interpolymers and lubricants containing them
US6258761B1 (en) * 1999-06-10 2001-07-10 The Lubrizol Corporation Lubricating oil additives
JP2006274058A (ja) * 2005-03-29 2006-10-12 Nippon Oil Corp 農業又は林業機械用潤滑油
US8716200B2 (en) 2006-09-13 2014-05-06 Ecolab Usa Inc. Conveyor lubricants including emulsion of a lipophilic compound and an emulsifier and/or an anionic surfactant and methods employing them

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FI66899C (fi) * 1983-02-11 1984-12-10 Kasvisoeljy Vaextolje Ab Oy Smoerjmedel med triglycerider som huvudkomponent
DE3419415A1 (de) * 1984-05-24 1985-11-28 Hans 7432 Urach Schur Herstellung von schmiermitteln, schaloelen und bohremulsionen aus umweltfreundlichen grundstoffen
ATE76658T1 (de) * 1984-11-21 1992-06-15 Lubrizol Corp Polymere zusammensetzungen, diese polymere zusammensetzungen enthaltende oelzusammensetzungen, transmissionsfluessigkeiten und hydraulikfluessigkeiten.
CA1275403C (en) * 1985-06-07 1990-10-23 Albert Rossi Lubricating oil composition containing dual additive combination for lowtemperature viscosity improvement

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MX9206249A (es) 1993-04-01
CA2095619C (en) 2003-07-08
AU2762592A (en) 1993-06-07
AU665786B2 (en) 1996-01-18
WO1993009209A1 (en) 1993-05-13
JPH06504088A (ja) 1994-05-12

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