Classifications

• • 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
  • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
  • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
  • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
  • C08F20/10—Esters
  • C08F20/12—Esters of monohydric alcohols or phenols
  • C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
• • 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
  • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
  • 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
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—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 type
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—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 type
  • C10M2209/082—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 type monocarboxylic
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—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 type
  • C10M2209/084—Acrylate; Methacrylate
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—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 type
  • C10M2209/086—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 type polycarboxylic, e.g. maleic acid
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
  • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
  • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
• • 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
  • C10N2070/00—Specific manufacturing methods for lubricant compositions
  • C10N2070/02—Concentrating of additives

Definitions

• This invention relates to new and valuable copolymers which, in addition to providing useful adherent surface protective coatings or films, are unexpectedly useful as lubricating oil additives.
• the invention also relates to lubricating oil compositions containing these copolymers.
• Lubricating oils particularly those used in internal combustion engines such as gasoline engines, diesel engines and the like, tend to become thinner and lose their lubricating efficiency as the engine reaches operating temperatures. Yet, if the oil is too thick initially in the engine, starting of the engine is diflicult under even ordinary temperature conditions. Consequently, some compromise in the selection of a particular oil is necessary in the lubricating of engines to the end that the oil will not be so thick at ordinary or low temperatures to prevent or unduly interfere with starting of the engine and which oil will yet not become so thin as to lose its lubricating efliciency as the operating temperatures of the engine are reached.
• the viscosity index, or V.I. (as determined by ASTM method D567-53) of the oil, is usually accepted as a measure of its high temperature performance, the higher the V.I., the better the performance.
• V.I. viscosity index
• a viscosity index improving additive would be one that is oleophobic at some preselected optimum low temperature, e.g., room temperature or below, and that would remain dispersed in the oil without precipitating out and without thickening the oil at these temperatures.
• the additive should become progressively more soluble and spread more homogeneously (on the molecular level), through the oil with the temperature rise to stiffen the oil to a degree exactly compensating for the decreased oil viscosity due to the increasing heating as the engine operating temperature is reached.
• the greater stabilizing effect at any given concentration of additive on the oil is obtained at the expense of thickening the oil at the 100 F. temperature with high molecular weight additives, or by sacrificing some of the possible viscosity index improvement by utilizing a lower molecular weight additive which reduces the initial thickening effect.
• the polymers of this invention are made by the copolymerization of aromatic and aliphatic esters of the same or different ethylene carboxylic acids, the acids being selected from the group containing from 3 to 5 carbon atoms, having molecular weights no greater than about and wherein the ethylenic double bond is conjugated with a carboxyl group.
• This class of acids may be represented by the structural formula wherein X is H, CH or COOH, Y is H, CH C H or CH COOH, and X and Y are not simultaneously COOH radicals.
• acids include acrylic, methacrylic, ethacrylic, itaconic, maleic and fumaric acids.
• acrylic, methacrylic and ethacrylic acids and esters readily copolymerize in widely varying proportions. Further, they are commercially available in quantity and considerable literature is available pertaining to their properties, greatly adding to the convenience of their use.
• Methacrylic acid is a particular preference in the use of these polymers as lube oil additives, since polymers made from esters thereof appear to serve better as pour point depressants than do those of acrylic acid esters.
• One of the comonomers is prepared by esterifying one of the above noted group of acids with a saturated aliphatic (which can be alicyclic) primary monohydric alcohol having from 1 to 12 carbon atoms and no more than one other atom in the skeletal structure thereof,'the other atom, or hetero-atom, when present, being oxygen and forming an ether linkage with adjacent carbon atoms.
• Preferred alcohols are the short chain aliphatic alcohols containing from about 1 to about 6 carbon atoms, such as methyl, ethyl, propyl, butyl, 2-ethyl butyl, amyl (amyl alcohol mixtures being readily available as fusel oil), and hexyl alcohols.
• the second comonomer is also an ester of an acid (which may be the same as or different from the acid of the first comonomer), selected from the group noted hereinbefore, the acid being esterified with an alkylphenyl-ether substituted lower 1,2-alkylene, i.e., ethylene or propylene, glycol having less than four alkylene oxy units in the glycol chain with the alkyl substituent of the alkyl-phenyl-ether group comprising from about 9 to about 18 carbon atoms.
• an alkylphenyl-ether substituted lower 1,2-alkylene i.e., ethylene or propylene
• glycol having less than four alkylene oxy units in the glycol chain with the alkyl substituent of the alkyl-phenyl-ether group comprising from about 9 to about 18 carbon atoms.
• substituted 1,2-alkylene glycols may be represented generally by the structural formula wherein R is an alkyl radical containing from about 8 to about 18 carbon atoms, R, is a methyl radical or hydrogen and n is an integer from 1 to 3.
• R is an alkyl radical containing from about 8 to about 18 carbon atoms
• R is a methyl radical or hydrogen
• n is an integer from 1 to 3.
• the preferred monomer is 3 pentadecyl phenoxyethyl methacylate (cardanoxy ethylmethacrylate structurally, the preferred comonomers may be represented as follows:
• alcohol residue and Z is as previously indicated, namely H or lower alkyl and preferably methyl, and
• Copolymers of long chain acrylates such as lauryl, stcaryl, cetyl acrylates and alpha-methylacrylates (methacrylates), etc.
• short chain acrylates such as ethyl, propyl, butyl, fusel oil acrylates and alpha methylacrylates (methacrylates) etc.
• many multi-grade lubricating oils contain minor amounts of these copolymers as viscosity index improving agents. They are, however, subject to the deficiencies noted hereinbefore.
• homopolyrners of the alkyl-phenoxy alkyl acrylate monomers which form one group of comonomers of the present invention also display viscosity index improving characteristics which are generally comparable to those of the open chain acrylate copolymer commercial additives of the type noted.
• These homopolyrners of aromatic substituted acrylate monomers sacrifice shear stability for significant V.I. improvement and are not useful as pour point depressants of the lubricating oils in which they are incorporated; in some instances they actually increase the pour point of the lubricating oil composition to a point considerably above that of the base lubricating oil.
• the polymers of the present invention are unexpectedly superior in certain fundamental respects as lubricating oil additives to both the copolymers of long and short chain acrylates containing no aromatic substituents and to homopolyrners of aromatic substituents and to homopolyrners of aromatic substituted acrylates per se.
• EXAMPLE I A tared, two liter, three neck flask equipped with stirrer, addition funnel and distillation set-up was loaded with 1200 grams (approx. 4 moles) of 3-pentadecyl phenol. Heat was applied thereto to raise the temperature thereof to approximately 60 C. whereupon the 3-pentadecyl phenol was converted to the liquid state. While being maintained at said temperature 40 grams (0.22 mole) of potassium hydroxide in methanol (30% concentration) was added thereto through the addition funnel.
• the mixture was topped in vacuo to C. at 1 mm. of mercury pressure. Then under atmospheric conditions the resultant alkaline mixture was heated to 163 C. and while being maintained at said temperature a stream of ethylene oxide was passed thereinto through a large capillary tube. The ethylene oxide was admitted under the aforesaid conditions over a period of about 2% hours whereupon 194 grams (4.4 moles) thereof had become absorbed or reacted with said alkaline mixture. Then the mass was cooled to about C. and neutralized with 15 grams concentrated hydrochloric acid in 15 grams water. This neutral mass was dehydrated at a temperature of 100 C. and 25 mm. of mercury pressure. The dehydrated mass was then filtered at l00ll0 C.
• This compound is readily esterified with a member of the acrylic acid series such as acrylic acid or methacrylic acid by reacting the compound in the presence of an acid with acrylate or methacrylate esters thereby forming by transesterification alkyl phenoxy-alkyl acrylic esters having the general formula:
• Z is H and the compound may be described as 3-pentadecyl phenoxyethyl acrylate.
• the foregoing compound may be also referred to as cardanoxy-ethyl acrylate.
• these compounds may be considered as alkyl-phenoxy-alkyl and alkyl phenoxy alkoxy alkyl acrylates.
• the corresponding methacrylate has also been prepared as have other similar alkyl-phenoxy terminated acrylates and methacrylates, among them being nonyl-phenoxyethyl acrylate, dodecyl-phenoxyethyl acrylate, and 3 pentadecyl phenoxy propyl acrylate.
• alkyl and alkoxy alkyl terminated acrylate comonomers have been obtained either through commercial channels or by laboratory preparation.
• these comonomers were ethyl acrylate, ethoxy ethylacrylate, fusel oil acrylate, ethyl methacrylate, n-butyl methacrylate, n-amyl methacrylate, 2-ethyl-butyl methacrylate and lauryl methacrylate. Since the manner of preparation of these materials is known in the art, a de tailed discussion of their preparation is not believed necessary.
• Copolymerizing the alkyl-phenoxy terminated acrylates with the alkyl or alkoxyalkyl terminated acrylates results in the production of the copolymers of this invention.
• these copolymers vary from translucent to transparent waxy materials to light colored rubbery solids. They are soluble in common organic solvents and adhere well to common structural materials such as wood and EXAMPLE II
• To a mixture of 80 parts by Weight of the acrylic acid ester of 3-pentadecylphenoxyethyl alcohol and 20 parts by weight of ethyl acrylate in 100 parts by weight of heptane Was added 2 parts by Weight benzoyl peroxide. The mixture was then heated with slight shaking at 60 C.
• the solution of polymer was diluted with parts by weight methanol, the polymer collected, Washed and dried.
• the resulting polymer was a light colored, rubbery material obtained in a yield of about 69%.
• the polymer was soluble to an extent of more than about 2% by Weight in a light mineral oil and possessed an inherent viscosity in benzene of 0.71.
• copolymers were prepared by the foregoing procedure with varying proportions of comonomers. In certain cases a 25 or 33% solution in heptane was used rather than the 50% solution noted above. Also, in some instances the temperature of copolymerization was about 55 C. rather than 60 C.
• polymerization occurs across the double bonds of the ethylenic residues of the starting acids so that the skeletal backbone of the polymer is composed of carbon to carbon bonds only, with the other substituents depending from this backbone as a side chain.
• the most useful copolymers are those wherein the alkyl-phenyl terminated monomer is present in its polymeric combined form in the polymer in amounts of about 20 to about 95 mol percent of the polymer.
• the polymer should have terminal alkyl groups in the side chain thereof having an average chain length of from about 6.5 to about carbon atoms.
• terminal alkyl group is meant either R, the alkyl group attached to the phenyl ring, or A, the alkyl (or alkoxyalkyl), group comprising the residue of the saturated monohydric primary alcohol, in the preferred monomer mixture.
• the average chain length of the terminal alkyl groups in the polymer is less than about 6.5, the polymer precipitates out of the base oil.
• the chain length average exceeds about 10, the polymer loses its high temperature thickening efiiciency.
• the average terminal alkyl group chain length of the polymer can be as low as about 5.5 without precipitating out of the oil.
• alkyl and alkoxy-alkyl acrylates and methacrylates are those containing about 6 carbons and less in the alkyl or alkoxy alkyl group, i.e., hexyl (and below), acrylates and .methacrylates.
• hexyl and below
• acrylates and .methacrylates As the number of carbon atoms in the alkyl chain is increased above about 6 carbon atoms in the alkyl acrylate comonomer, the resulting polymers tend to become more soluble in the base oil and evidence a corresponding decrease in viscosity index improvement over those polymers utilizing the shorter chain alkyl acrylates.
• a convenient method for obtaining a rough estimate of the molecular weight is through determinations of the inherent viscosities of the polymers.
• the inherent viscosity is a function of the molecular weight and is repre- 1n (n solution I: n solvent wherein C is concentration in grams of polymer per 100 ml. of solvent and 1 solution and a solvent are the viscosities in any consistent units, of the solution and the solvent.
• the solvent is benzene and the concentration of polymer in solution is 0.2 gram polymer per 100 ml. solvent.
• the inherent viscosity may be considered for purposes of this case as a measure of the bulkiness of the polymer in solution.
• its bulkiness as determined by its inherent viscosity in the oil should increase with increasing temperatures and provide a ratio between inherent viscosities at a higher and a lower base temperature greater than unity.
• temperatures of 100 and 210 F. have been chosen as the low and high base temperatures so that molecular weight comparisons (1; in benzene), as well as the effective increase in the bulk of the polymeric solute can be correlated with the viscosity index improvement. This comparison may be made by comparing the viscosity ratio (V.R.) which may be defined as:
• V.I. the inherent viscosities at the high and low temperatures are determined from viscosity measurements of 2% solutions of the polymer in the base lubricating oil. This comparison more adequately reflects the actual thickening eifect of the polymer in the oil at high temperatures than does the V1.
• the base oil designated as base oil #5 in Table II following is a light, highly refined Pennsylvania type mineral oil composed essentially of a mixture of parafiins.
• T abl a ll Copolymer Kinematic Terminal Idcntifica- Mol percent [1;] in benzene viscosity Viscosity index Viscosity ratio chain length tio combined M1 at 100 F. (average) M1 M2 (eentistokes) oil #5 17. 93 111 *All of these comprise copolymers of long and short chain methaerylatcs, generally principally of lauryl and n-butyl methacrylates.
• copolymers 1-10 display equivalent or better viscosity index improvement than do the commercial additives while invariably possessing a lesser thickening efiect on the base oil at the 100 F. base temperature for additives of the same [1;] range.
• Commercial additive C which has an inherent viscosity of 1.40 in benzene as compared with copolymers 7 and 11 having respective inherent viscosities of 1.32 and 1.42.
• the commercial additive increased the kinematic viscosity of the base oil approximately 29 centistokes at 100 F., whereas copolymer number 7 increased it only 12 centistokes and copolymer number 11 only centistokes while bettering the viscosity index improvement of the commercial additive by 12 and 19 V.I. units respectively.
• the last two members, 12 and 13, of Table II are much less effective than the other copolymers of the series, as viscosity index improvers.
• the preferred copolymers are those having terminal alkyl groups in the side chain thereof with an average chain length of about 6.5-l0.0 carbon atoms. In the two copolymers noted the average terminal chain length is over 12 and their performance is poor.
• base oil #9 is a highly refined Mid-Continent oil useful as a light lubricating oil for automobile engines.
• the polymers selected for comparison in this Table III with additives A, B and C were selected on the basis that they encompassed the range of molecular weight materials covered by the commercial additives. Similar results were obtained in comparing these polymers with laboratory prepared polymers of lauryl methacrylateethyl methacrylate (57:43), lauryl methacrylate-n-butyl methacrylate (51:49); and lauryl methacrylate-ethoxy ethyl acrylate (58:42), the parenthetical proportions being molar ratios of combined monomers in the polymer.
• Base oil 9 32. 60 100 MA n-AM 0 54 41.78 147 1. 64 0.78 50. 78 156 1. 59 1. 42 62. 40 161 1. 78 0. 61 53. 49 143 1. l7 0. 98 60. 26 147 1. 20 1.15 58. 29 152 1. 34
• copolymers 6, 8 and 11 display a greater increase in bulkiness, evidenced by the higher viscosity ratios, than do the commercial additives. The practical effect of this increase is evidenced in the 100 F. viscosity column as compared to the viscosity improvement.
• copolymer #6 increased the 100 F. oil viscosity only about 9 centistokes while increasing the V.I. by 47 points, while commercial additive B, which also increased the V.I. by 47 points, increased the 100 F. oil viscosity about 27 centistokes.
• the polymers of this invention may be usefully incorporated into lubricating oils in amounts of from about of 1% to about 10% by weight, and preferably not over about 5% by weight.
• the polymers may be marketed or stored in concentrations up to about 30 or 40% by weight in the base oil.
• the base oil may also have added thereto, emulsion inhibitors, stabilizers, detergents and/ or other additives as may be found to be desirable or customary.
• a copolymer of monomeric esters of polymerizable ethylene carboxylic acids containing from 3 to 5 carbon atoms and having molecular weights no greater than about 130 and wherein the ethylenic double bond is conjugated with a carboxyl group (1) one of said acids being esterified with a saturated primary monohydric alcohol having from 1 to 12 carbon atoms and no more than one other atom in the skeletal structure thereof, said other atom when present being oxygen, (2) the other of said acids being esterified with an alkyl-phenylether substituted lower 1,2-alkylene glycol having less than four alkylene oxy units in the glycol chain, the alkyl substituent of said alkyl-phenyl-ether group comprising from about 9 to about 18 carbon atoms, said copolymer having a terminal alkyl group in the side chain thereof having an average chain length of about 5.510.0 carbon atoms.
• a copolymer of monomeric esters of polymerizable ethylene carboxylic acids containing from 3 to 5 carbon atoms and having molecular weights no greater than about 130 and wherein the ethylenic double bond is conjugated with a carboxyl group (1) one of said acids being esterified with a saturated primary monohydric alcohol having from 1 to 12 carbon atoms and no more than one other atom in the skeletal structure thereof, said other atom when present being oxygen, and forming an ether linkage with adjacent carbon atoms, (2) the other of said acids being esterified with an alkyl-phenyl-ether substituted ethylene glycol having less than four ethylene oxy units in the glycol chain, the alkyl substituent of said alkylphenyl-ether group comprising from about 9 to about 18 carbon atoms, said copolymer comprising between about 20 and about 90 mol percent (2) and having a terminal alkyl group in the side chain thereof having an average chain length of about 5.510.0 carbon atoms.

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Chemistry (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Lubricants (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

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• 1959
  • 1959-02-18 DE DEM40531A patent/DE1165858B/de active Pending
  • 1959-02-18 FR FR787062A patent/FR1222894A/fr not_active Expired
  • 1959-02-19 GB GB5787/59A patent/GB917281A/en not_active Expired
• 1961
  • 1961-08-29 US US141558A patent/US3214406A/en not_active Expired - Lifetime

Non-Patent Citations (1)

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