US3249545A - Lubricating composition containing non-ash forming additives - Google Patents

Lubricating composition containing non-ash forming additives Download PDF

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Publication number
US3249545A
US3249545A US230279A US23027962A US3249545A US 3249545 A US3249545 A US 3249545A US 230279 A US230279 A US 230279A US 23027962 A US23027962 A US 23027962A US 3249545 A US3249545 A US 3249545A
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Prior art keywords
bis
hydroxyphenyl
composition
methane
acid
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US230279A
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Inventor
Henricus G P Van Der Voort
Krukziener Maurits
Jan B Baurdoux
Hendrik Van Oosten
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Shell USA Inc
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Shell Oil Co
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    • 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
    • C10M145/16—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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    • 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
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
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    • 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
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    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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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
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • 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
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy
    • 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

  • ash deposits formed in the combustion chamber and on the valves causes engine operating difiiculties as, for instance premature ignition of the air/fuel mixture, etc.
  • ashless additives have been developed such as non-ash forming basic and essentially neutral nitrogen-containing dispersants of high molecular weight such as copolymers of polymerizable amines or amides with long-chain acrylate esters.
  • Ashless additives of this type are available commercially under the trade names of LOA-564 or 565, Acryloid 315X, 917 or 966 and described in US Patent 2,737,469 and Belgian Patent 550,422 respectively.
  • These non-ash forming polymeric compounds are good detergents but under extreme pressure conditions lack stability and wear inhibiting properties and are also inefiective as sludge and corrosion inhibitors. Attempts to overcome these deficiencies by modification of these polymers or by use of auxiliary additives in combination with these polymers has met with little success. Thus modifying polymers by introducing certain groups tends often to destroy or reduce the original desirable properties which the polymers possess.
  • auxiliary additives appear to be promising stabilizers and wear inhibitors they are usually metalcontaining compounds such as metal sulfonates or metal carboxylates. For reasons stated, compounds of this type are to be avoided and because of their tendency to com plex with the polymer and form sludge.
  • detergent copolymers per se also lack anti-oxidant and Wear inhibiting properties and primarilyare added to lubricants as detergent-dispersant additives. Therefore, the additive combination imparts to base lubricants, unexpected unusual properties.
  • the copolymeric additives (l) are copolymers with ester groups derived from monomeric esters of unsaturated monocarboxylic acids, such as acrylic acid, methacrylic acid, crotonic acid, tiglic acid and angelic acid, and monohydric alcohols, such as the octanols, lauryl alcohol and stearyl alcohol, and (2) ester groups derived from monomeric esters of unsaturated carboxylic acids as mentioned hereinbefore, and polyhydric alcohols, such as glycols, trivalent alcohols, such as glycerine and higher alcohols, such as erythrytol, pentaerythrytol, mannitol and the like.
  • ester groups derived from monomeric esters of unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, tiglic acid and angelic acid
  • monohydric alcohols such as the octanols, lauryl alcohol and stearyl alcohol
  • copolymers with ester groups derived from di-esters of the alcohols mentioned hereinbefore, and unsaturated dicarboxylic acids such as maleic acid, fumaric acid, mesaconic acid, citraconic acid and the like.
  • Copolymers with ester groups derived from the aforesaid alcohols and both an unsaturtaed monocarboxylic acid and an unsaturated dicarboxylic acid for instance a copolymer derived from mixtures of methacrylate esters and di-esters of maleic acid also can be used in composition of the present invention.
  • unsaturated monocarboxylic acids e.g. methacrylic and acrylic acids are preferred and in the case of the polymerizable ester of a polyhydric alcohol unsaturates esters of ethylene glycols are preferred.
  • copolymeric esters of groups (A) and (B) can be derived from mixtures of esters from each groups (A) and (B).
  • copolymers can be prepared by copolymerization of an ester mixture obtained from an unsaturated acid and an alcohol mixture such as coconut fatty alcohols, with esters obtained from an unsaturated acid and a polyhydric alcohol or mixtures of polyhydric alcohols.
  • the detergent-dispersant copolymers of the present invention can be modified and viscosity index and pour depressant properties imparted thereto by forming crosslinked polymers therefrom by copolymerizing the copolymers of the present invetion with diolefinic compound such as a dimethacrylate ester of ethylene glycol, divinyl esters, e.g. divinyl adipate and the like fully described in Henricus G. P. van der Voorts copending patent application Serial No. 230,278 filed Oct. 12, 1962.
  • diolefinic compound such as a dimethacrylate ester of ethylene glycol, divinyl esters, e.g. divinyl adipate and the like fully described in Henricus G. P. van der Voorts copending patent application Serial No. 230,278 filed Oct. 12, 1962.
  • COPOLYMER I Copolymer of stearyl methacrylate, lauryl methacrylate and Z-hydroxyethyl methacrylate in the molar ratio of 5 :5 :3.
  • the intrinsic viscosity of the copolymer determined at 989 C. in an extracted parafiinic lubricating oil distillate, was 0.65 dl./ g.
  • COPOLYMER II Copolymer of stearyl methacrylate, lauryl methacrylate, Z-hydroxyethyl methacrylate and the dimethacrylate ester of ethylene glycol in the molar ratio of 5 :5 23:0.03.
  • the intrinsic viscosity of the copolymer determined at 98.9 C. in an extracted parafiinic lubricating oil distillate, was 0.65 dl./ g.
  • the other additive which is used in combination with the essential detergent copolymeric additive (1) of this invention is (2) an alkylated bisphenol having the formula OH OH wherein R is a hydrocarbyl radical, preferably a C alkyl radical, y is an integer of l to 4, preferably 1 or 2, X stands for S-, SS, Se, -SCH --CH O-CH CHR, CR -(CH NH-, .O, and wherein R stands for methyl or ethyl and m stands for an integer from 1 to 3.
  • the preferred alkylated bisphenols are those having a sulfur bridge or a methylene bridge.
  • the alkylated bisphenols may contain from 1 to 8 alkyl groups, but preferably they contain from 2 to 6 alkyl groups. Alkylated bisphenols having 4 alkyl groups are particularly preferred. Each of the alkyl groups may contain from 1 to 10 carbon atoms, preferably 2 to 6 carbon atoms and especially 4 carbon atoms. Furthermore, the alkyl groups contained by any particular bisphenol may be the same or different and may also be primary, secondary, or tertiary alkyl groups. Bisphenols containing at least one tertiary alkyl group are particularly preferred.
  • alkylated bispenols which may be used according to' the invention there are mentioned bis 3-ethyl-4-hydroxyphenyl disulfide,
  • alkylated bis-phenols having a sulfur bridge examples include bis 2 5-dipentyl-4-hydroxyphenyl) sulfide,
  • alkylated bisphenols having a methylene bridge examples include his 2 3-di-tertiary butyl-4-hydr-oxyphenyl methane,
  • the alkylated bisphenol may be prepared by any of the methods known in the art of bisphenols as starting materials and condensing them together by any of the established methods.
  • the lubricating oil compositions according to the invention may be further improved by addition of small amounts of other additives which are metal-free organic phosphorus-containing compounds such as alkyl, cycloalkyl, alkaryl, aralkyl, and aryl phosphites, phosphates,
  • additives which are metal-free organic phosphorus-containing compounds such as alkyl, cycloalkyl, alkaryl, aralkyl, and aryl phosphites, phosphates,
  • phosphonates and their thioderivatives, such as C alkyl phosphites, e.g. di and tributyl, octyl, lauryl, stearyl, cyclohexyl, benzyl, cresyl, phenyl phosphites or phosphates, as well as their thio-derivatives; P S -terpene reaction product; organo phosphonates, e.g.
  • esters of pentavalent phosphorus acids such as diphenyl, .dicresyl, triphenyl, tricresyl, .trilauryl and tristearyl phosphate, P S -terpene reaction products and mixtures thereof are preferred.
  • the concentrations of the various components of the lubricant compositions may vary within wide limits.
  • the copolymers can be used in concentrations varying from 0.1 to 10% by Weight, the bisphenol, in concentrations yarying from 0.01 to 5% by Weight and the phosphorus-containing compound in concentrations varying, for instance, from 0.01 to 5% by weight.
  • lubricant compositions are prepared with a content of copolymers varying from 0.5 to 2% by weight, a content of bisphenol varying from 0.5 to 2% by Weight and, if a phosphate, e.g. an aryl phosphate is used, it may vary from 0.5 to 2% by weight.
  • a mineral lubricating oil is used for preparing the lubricant compositions according to the invention.
  • the lubricant composition it may be an advantage first to prepare a concentrated solution of the copolymer, the bisphenol and, if used, thephosphate, in a solvent or a lubricant and subsequently, for instance elsewhere, to dilute the concentrated solution with a lubricant and to remove by distillation under reduced'pressure or by steam distillation.
  • a concentrated solution of the copolymer, the bisphenol and, if used, thephosphate in a solvent or a lubricant and subsequently, for instance elsewhere, to dilute the concentrated solution with a lubricant and to remove by distillation under reduced'pressure or by steam distillation.
  • Composition B Base oil: as in A 97.75 Copolymer II 1.5 Bis(3,5-di-tert-butyl-4-hydroxyphenyl)methane 0.75
  • Composition E Base oil: as in C 99.25 Bis(3,5-di-tert-butyl-4-hydroxyphenyl)methane 0.75
  • Composition F Base oil: as in C ,96.75 Copolymer I 1.5 Bis 3 ,5 -di-tert-butyl-4-hydroxyphenyl methane 0.75
  • compositions A and B were determined according to Dean and Davis (A. Bondi, Physical Chemistry of Lubricating Oils, 1951, pp. 50 ff.) and the results of these measurements are given in Table I.
  • a mineral lubricating 'oil composition comprising a major amount of mineral lubricating oil and from about 0.1% to about 10% of an oil-soluble copolymer of a mixture of dissimilar C1248 alkyl methacrylates and 2- hydroxyethyl methacrylate, the copolymer having an intrinsic viscosity of around 0.65 dl./g. and from about 0.5% to about 2% of bis(3,5-ditertiarybutyl-4-hydroxyphenyl)methane.
  • a mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from about 0.1% to about 10% of an oil-soluble copolymer of stearyl methacrylate,-1auryl methacrylate and 2-hydroxyethyl methacrylate having an intrinsic viscosity of about 0.65 dl./g. and from about 0.5%-to about 2% of bis(3,5- ditertiarybutyl-4-hydroxyphenyl)methane.

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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)
US230279A 1962-03-23 1962-10-12 Lubricating composition containing non-ash forming additives Expired - Lifetime US3249545A (en)

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BE (1) BE629904A (xx)
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GB (1) GB965195A (xx)
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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU662159B2 (en) * 1992-03-20 1995-08-24 Rohm And Haas Company Dispersant poly(meth)acrylate viscosity index improvers
WO1999027037A1 (de) * 1997-11-21 1999-06-03 Rohmax Additives Gmbh Additiv für biodiesel und biobrennstofföle
US6712991B2 (en) 1993-07-23 2004-03-30 Rohmax Additives Gmbh Method of making a copolymer useful as viscosity index improving additive for hydraulic fluid
US20050119134A1 (en) * 2003-11-28 2005-06-02 Chevron Oronite S.A. Additive composition for transmission oil
US20080153724A1 (en) * 2002-07-30 2008-06-26 Pierre Tequi Additive composition for transmission oil containing hydrated alkali metal borate and hexagonal boron nitride
DE102007036856A1 (de) 2007-08-06 2009-02-26 Evonik Rohmax Additives Gmbh Verwendung von Estergruppen-umfassenden Polymeren als Antifatigue-Additive
WO2009095482A2 (en) * 2008-01-30 2009-08-06 Shell Internationale Research Maatschappij B.V. Lubricating composition
WO2010102903A1 (de) 2009-03-10 2010-09-16 Evonik Rohmax Additives Gmbh Verwendung von kammpolymeren als antifatigue-additive
WO2010142668A1 (en) * 2009-06-09 2010-12-16 Shell Internationale Research Maatschappij B.V. Lubricating composition
US20130079420A1 (en) * 2010-06-22 2013-03-28 Societe D'exploitation Des Produits Pour Les Industries Chimiques Seppic Novel thickening polymer for ionic oil phases free of monomers
EP2626405A1 (en) 2012-02-10 2013-08-14 Ab Nanol Technologies Oy Lubricant composition
EP2695932A1 (en) 2012-08-08 2014-02-12 Ab Nanol Technologies Oy Grease composition
WO2015172846A1 (en) 2014-05-16 2015-11-19 Ab Nanol Technologies Oy Additive composition for lubricants

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US3056764A (en) * 1959-05-15 1962-10-02 Canadian Ind Manufacture of polymers from polymers of unsaturated acids
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US2157873A (en) * 1935-12-02 1939-05-09 Shell Dev Process for extreme pressure lubricants
US2681987A (en) * 1946-06-05 1954-06-22 Us Navy Transmission system for radio echo detection systems
US2636861A (en) * 1950-06-09 1953-04-28 Shell Dev Hydraulic fluid
US2944086A (en) * 1955-09-23 1960-07-05 Ethyl Corp 1, 1-bis(3, 5-dialkyl-4-hydroxyphenyl) methanes
US2892819A (en) * 1956-03-29 1959-06-30 California Research Corp Detergent copolymers
US3002959A (en) * 1956-06-25 1961-10-03 Devoe & Raynolds Co Inc Hydroxyl-containing copolymers and their preparation
US3028367A (en) * 1958-04-14 1962-04-03 Rohm & Haas Copolymers of hydroxyalkyl acrylates and methacrylates and alkyl acrylates and methacrylates reacted with diisocyanates
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Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU662159B2 (en) * 1992-03-20 1995-08-24 Rohm And Haas Company Dispersant poly(meth)acrylate viscosity index improvers
US6712991B2 (en) 1993-07-23 2004-03-30 Rohmax Additives Gmbh Method of making a copolymer useful as viscosity index improving additive for hydraulic fluid
WO1999027037A1 (de) * 1997-11-21 1999-06-03 Rohmax Additives Gmbh Additiv für biodiesel und biobrennstofföle
US6409778B1 (en) * 1997-11-21 2002-06-25 Rohmax Additives Gmbh Additive for biodiesel and biofuel oils
US20080153724A1 (en) * 2002-07-30 2008-06-26 Pierre Tequi Additive composition for transmission oil containing hydrated alkali metal borate and hexagonal boron nitride
US20050119134A1 (en) * 2003-11-28 2005-06-02 Chevron Oronite S.A. Additive composition for transmission oil
US20080280793A1 (en) * 2003-11-28 2008-11-13 Chevron Oronite S.A. Additive composition for transmission oil containing hexagonal boron nitride and polymethacrylate or dispersant olefin co-polymer
DE102007036856A1 (de) 2007-08-06 2009-02-26 Evonik Rohmax Additives Gmbh Verwendung von Estergruppen-umfassenden Polymeren als Antifatigue-Additive
WO2009095482A2 (en) * 2008-01-30 2009-08-06 Shell Internationale Research Maatschappij B.V. Lubricating composition
WO2009095482A3 (en) * 2008-01-30 2009-10-29 Shell Internationale Research Maatschappij B.V. Lubricating composition
WO2010102903A1 (de) 2009-03-10 2010-09-16 Evonik Rohmax Additives Gmbh Verwendung von kammpolymeren als antifatigue-additive
DE102009001446A1 (de) 2009-03-10 2010-09-23 Evonik Rohmax Additives Gmbh Verwendung von Kammpolymeren als Antifatigue-Additive
WO2010142668A1 (en) * 2009-06-09 2010-12-16 Shell Internationale Research Maatschappij B.V. Lubricating composition
US20130079420A1 (en) * 2010-06-22 2013-03-28 Societe D'exploitation Des Produits Pour Les Industries Chimiques Seppic Novel thickening polymer for ionic oil phases free of monomers
US8937101B2 (en) * 2010-06-22 2015-01-20 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic Thickening polymer for ionic oil phases free of monomers
US20150094440A1 (en) * 2010-06-22 2015-04-02 Societe D'exploitation Des Produits Pour Les Industries Chimiques Seppic Novel thickening polymer for ionic oil phases free of monomers
US9243094B2 (en) * 2010-06-22 2016-01-26 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic Thickening polymer for ionic oil phases free of monomers
EP2626405A1 (en) 2012-02-10 2013-08-14 Ab Nanol Technologies Oy Lubricant composition
EP2695932A1 (en) 2012-08-08 2014-02-12 Ab Nanol Technologies Oy Grease composition
WO2014023707A1 (en) 2012-08-08 2014-02-13 Ab Nanol Technologies Oy Grease composition
WO2015172846A1 (en) 2014-05-16 2015-11-19 Ab Nanol Technologies Oy Additive composition for lubricants
US10144896B2 (en) 2014-05-16 2018-12-04 Ab Nanol Technologies Oy Composition

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Publication number Publication date
MY6500080A (en) 1965-12-31
DE1257329B (de) 1967-12-28
CH446582A (de) 1967-11-15
GB965195A (en) 1964-07-29
BE629904A (xx)
NL276299A (xx)
DK104992C (da) 1966-08-01

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