GB1068235A - Additives for lubricating compositions - Google Patents

Additives for lubricating compositions

Info

Publication number
GB1068235A
GB1068235A GB28456/64A GB2845664A GB1068235A GB 1068235 A GB1068235 A GB 1068235A GB 28456/64 A GB28456/64 A GB 28456/64A GB 2845664 A GB2845664 A GB 2845664A GB 1068235 A GB1068235 A GB 1068235A
Authority
GB
United Kingdom
Prior art keywords
polyisobutylene
dicyandiamide
reaction product
oil
succinic anhydride
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.)
Expired
Application number
GB28456/64A
Inventor
John Scotchford Elliott
Eric Deschamp Edwards
Gerald John Joseph Jayne
Richard House
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.)
Castrol Ltd
Original Assignee
Castrol Ltd
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 Castrol Ltd filed Critical Castrol Ltd
Priority to GB28456/64A priority Critical patent/GB1068235A/en
Priority to BE666544A priority patent/BE666544A/xx
Priority to FR23871A priority patent/FR1450694A/en
Priority to DK348765AA priority patent/DK116954B/en
Priority to US470564A priority patent/US3338831A/en
Priority to NL656508794A priority patent/NL139039B/en
Priority to DE19651594380 priority patent/DE1594380A1/en
Publication of GB1068235A publication Critical patent/GB1068235A/en
Expired legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/56Amides; Imides
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • C08F8/30Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027Neutral salts thereof
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/028Overbased salts thereof
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/282Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/34Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08Macromolecular 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
    • C10M2209/084Acrylate; Methacrylate
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064Di- and triaryl amines
    • C10M2215/065Phenyl-Naphthyl amines
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    • C10M2215/08Amides
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08Amides
    • C10M2215/082Amides containing hydroxyl groups; Alkoxylated derivatives
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    • C10M2215/086Imides
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/221Six-membered rings containing nitrogen and carbon only
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226Morpholines
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26Amines
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    • C10M2215/30Heterocyclic compounds
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046Overbasedsulfonic acid salts
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088Neutral salts
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    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089Overbased salts
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108Phenothiazine
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
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    • C10N2010/04Groups 2 or 12
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    • C10N2070/00Specific manufacturing methods for lubricant compositions
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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (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)

Abstract

Lubricating compositions comprise a lubricating oil and a minor proportion, sufficient to provide the desired degree of cold sludge dispercency or detergency, of an additive which is the reaction product of (a) a monoalkenyl substituted succinic anhydride wherein the alkenyl group has a molecular weight of at least 700; and (b) a reaction product of dicyandiamide with a primary alkylene polyamine having at least two primary amino groups and containing the group <FORM:1068235/C4-C5/1> where A is 2 to 4. Preferred additives are obtained by reacting polyisobutylene/maleic anhydride adducts with reaction products of dicyandiamide with polyethylene polyamines, imino bis propylamine and polyethylene imines. The oil may be a mineral oil, solvent refined mineral oil or mixture thereof, or a spindle oil, and the compositions may also comprise copper deactivators, pour point depressants, antioxidants, viscosity index improvers and other conventional additives, particularly zinc dialkyl dithiophosphates, alkaline earth metal petroleum sulphonates, phenates or phenol sulphides, alkaline earth metal salts of phosphosulphurized hydrocarbons, and copolymers of long chain alkyl methacrylates with vinyl pyridine or N-vinyl pyrrolidone. Many examples are given of lubricating compositions comprising mineral oils, reaction products of polyisobutylene succinic anhydride with reaction products of dicyandiamide and triethylene tetramine, diethylene triamine, tetraethylene pentamine, pentaethylene hexamine and imino bis propylamine, together with other additives such as zinc dialkyl dithiophosphates derived from isopropanol and methyl butyl carbinol or from isopropanol and 1-methylheptyl alcohol, barium salts of phosphosulphurized polyisobutylene and alkyl methacrylate copolymers. Example 41 describes a composition of di(2-ethylhexyl) sebacate, an additive of the invention wherein the alkenyl group is polyisobutylene and the amine is tetraethylenepentamine, phenyl-a -naphthylamine, 3,7-dioctyl phenothiazine and benzotriazole.ALSO:An additive for a lubricating oil is a reaction product of (a) a mono alkenyl substituted succinic anhydride wherein the alkenyl group has a molecular weight of at least 700 and (b) a reaction product of dicyandiamide with a primary alkylene polyamine having at least two primary amino groups and containing the group <FORM:1068235/C3/1> where A is 2 to 4. The monoalkenyl substituted succinic anhydride may be obtained by reaction between a normally liquid oil soluble polyolefine having a molecular weight of 700 to 3000 and maleic anhydride. Reaction product (b) is preferably prepared at a temperature from 240 DEG to 280 DEG C. and the molar ratio of (a) to (b) may be from 1:1 to 5:1. The alkylene polyamine preferably has the formula H2N-(RNH)n-RNH2 where R is an alkylene radical, preferably -CH2CH2- and n is an integer from 1 to 5 or more. Other alkylene polyamines may also be used e.g. imino bis propylamine; polymerization products of ethylene imine and a mixture of isomeric polyethylene hexamines and related hexamines containing piperazine rings and 12 C atoms. In the examples polyisobutenyl succinic anhydride is prepared either (i) by refluxing polyisobutylene with maleic anhydride and di-t-butyl peroxide in toluene, distilling off toluene, treating with hexane and then distilling off the hexane or (ii) refluxing polyisobutylene with maleic anhydride and then treating with hexane. The products are reacted with reaction products of dicyandiamide and triethylene tetramine, diethylene triamine, tetraethylene pentamine, pentaethylene hexamine and imino bis propylamine.
GB28456/64A 1964-07-09 1964-07-09 Additives for lubricating compositions Expired GB1068235A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
GB28456/64A GB1068235A (en) 1964-07-09 1964-07-09 Additives for lubricating compositions
BE666544A BE666544A (en) 1964-07-09 1965-07-07
FR23871A FR1450694A (en) 1964-07-09 1965-07-08 Additives for lubricating compositions, and lubricating compositions containing these additives
DK348765AA DK116954B (en) 1964-07-09 1965-07-08 Lubricating oil for internal combustion engines, containing an additive with high temperature cleaning ability and cold sludge dispersibility.
US470564A US3338831A (en) 1964-07-09 1965-07-08 Additives for lubricating compositions
NL656508794A NL139039B (en) 1964-07-09 1965-07-08 PROCESS FOR PREPARING A LUBRICANT OIL.
DE19651594380 DE1594380A1 (en) 1964-07-09 1965-07-09 Additives for lubricant preparations

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB28456/64A GB1068235A (en) 1964-07-09 1964-07-09 Additives for lubricating compositions

Publications (1)

Publication Number Publication Date
GB1068235A true GB1068235A (en) 1967-05-10

Family

ID=10275917

Family Applications (1)

Application Number Title Priority Date Filing Date
GB28456/64A Expired GB1068235A (en) 1964-07-09 1964-07-09 Additives for lubricating compositions

Country Status (7)

Country Link
US (1) US3338831A (en)
BE (1) BE666544A (en)
DE (1) DE1594380A1 (en)
DK (1) DK116954B (en)
FR (1) FR1450694A (en)
GB (1) GB1068235A (en)
NL (1) NL139039B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3399138A (en) * 1967-10-11 1968-08-27 Monsanto Co Triazines
US4743388A (en) * 1986-07-21 1988-05-10 Westvaco Corporation Complex amide carboxylate lubricant rust inhibitor additive for metal working fluids
CN115011065B (en) * 2022-06-14 2023-10-27 浙江长盛滑动轴承股份有限公司 Wear-resistant lubricating composite material with oily polyoxymethylene, composite board and preparation method

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1248643B (en) * 1959-03-30 1967-08-31 The Lubrizol Corporation, Cleveland, Ohio (V. St. A.) Process for the preparation of oil-soluble aylated amines

Also Published As

Publication number Publication date
US3338831A (en) 1967-08-29
DE1594380A1 (en) 1972-04-27
NL139039B (en) 1973-06-15
DK116954B (en) 1970-03-02
FR1450694A (en) 1966-08-26
BE666544A (en) 1965-11-03
NL6508794A (en) 1966-01-10

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