GB1459403A - Lubricant additives their preparation and compositions containing them - Google Patents
Lubricant additives their preparation and compositions containing themInfo
- Publication number
- GB1459403A GB1459403A GB1917373A GB1917373A GB1459403A GB 1459403 A GB1459403 A GB 1459403A GB 1917373 A GB1917373 A GB 1917373A GB 1917373 A GB1917373 A GB 1917373A GB 1459403 A GB1459403 A GB 1459403A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polyisobutenylphenol
- acid
- glyoxylic acid
- tetraethylene pentamine
- polyolefin
- 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
Links
- 239000003879 lubricant additive Substances 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 abstract 12
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 abstract 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 125000003368 amide group Chemical group 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 abstract 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 abstract 2
- 229920000768 polyamine Polymers 0.000 abstract 2
- 229920000098 polyolefin Polymers 0.000 abstract 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 2
- 229940014800 succinic anhydride Drugs 0.000 abstract 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 abstract 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 abstract 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 abstract 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- 229920002367 Polyisobutene Polymers 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 abstract 1
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 abstract 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- -1 hydroxyalkyl amine Chemical class 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000005027 hydroxyaryl group Chemical group 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 229940107700 pyruvic acid Drugs 0.000 abstract 1
- 239000008117 stearic acid Substances 0.000 abstract 1
- 239000001384 succinic acid Substances 0.000 abstract 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 abstract 1
- 229960001124 trientine Drugs 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
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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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] containing hydroxyl groups; Alkoxylated derivatives
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/12—Partial amides of polycarboxylic acids
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/26—Amines
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- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/28—Amides; Imides
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- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/30—Heterocyclic compounds
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- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
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- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/042—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds between the nitrogen-containing monomer and an aldehyde or ketone
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- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/043—Mannich bases
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- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/088—Neutral salts
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
-
- 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
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
1459403 Polyolefin derivatives ETHYL COOPER Ltd 11 April 1974 [19 April 1973] 19173/73 Heading C3P [Also in Division C5] Compounds of formula where each R<SP>1</SP> is H or alkyl provided that at least one is an alkyl group containing at least 30 carbon atoms derived from a polyolefin; R<SP>2</SP> is hydrogen or is a group of formula in which m is 0 or an integer; R<SP>4</SP> is hydrogen or is -ZR<SP>6</SP> in which Z is a sulphur atom, a chain of sulphur atoms or is absent and R<SP>6</SP> is alkyl or hydroxyaralkyl when Z is absent or is hydroxyaryl or hydroxyaralkyl when Z is present; R<SP>5</SP> is H, methyl or -CH 2 CH 2 COA; and each -COA is an ester or amide group provided that at least one is an amide group having a hydroxyalkyl or aminoalkyl group attached to the nitrogen atom; may be used as lubricant additives; and may be prepared by reacting bis(phenol substituted) carboxylic acids or derivatives thereof with a polyamine or hydroxyalkyl amine. R<SP>1</SP> may be derived from a polyisobutylene or polypropyllene. The products may be further reacted with carboxylic acids or derivatives, e.g. a polyolefin-substituted succinic acid or anhydride; aldehydes and/or ketones; and aldehydes and phenols to give Mannich bases. Examples describe the reaction of (1-9, 12-17, 26, 27 and 35) polyisobutenylphenol, glyoxylic acid and tetraethylene pentamine, and optionally (12 and 13) polyisobutenyl succinic anhydrides, (14) dodecanyl succinic anhydride, (15) formalin and polyisobutenylphenol, (16) formalin and nonylphenol, (17) benzaldehyde and (32) stearic acid; glyoxylic acid and tetraethylene pentamine with (10) thiobis(polyisobutenylphenol) and (11) methylene bis(polyisobutenylphenol); polyisobutenyl phenol and glyoxylic acid with (18) a polyamine, (19) dipropylene triamine, (20) ethylene diamine, (21) a tetraethylenepentamine/dicyandiamide reaction product, (22) dimethylaminopropylamine, (23) bisaminopropyl piperazine, (24) N- (2 - aminoethyl)ethanolamine and (25) bishexamethylenetriamine; (28) polyisobutenylphenol, nonylphenol, glyoxylic acid and tetraethylenepentamine; (29) polypropenylphenol, glyoxylic acid and triethylene tetramine; (30) polybutenyl o-cresol, glyoxylic acid and pentaethylene hexamine; (31) polybutenylphenol, 2- oxo-glutaric acid and tetraethylene pentamine; and (33 and 34) polyisobutenylphenol, pyruvic acid and tetraethylene pentamine.
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1917373A GB1459403A (en) | 1973-04-19 | 1973-04-19 | Lubricant additives their preparation and compositions containing them |
| AR253344A AR205535A1 (en) | 1973-04-19 | 1974-01-01 | CARBOXYLAMIDES BIS (PHENOLSUBSTITUTED) USEFUL AS ADDITIVES FOR LUBRICANTS THEIR PREPARATION AND USE |
| US05/462,092 US3966807A (en) | 1973-04-19 | 1974-04-18 | Lubricant additives, their preparation and compositions containing them |
| IT21642/74A IT1012586B (en) | 1973-04-19 | 1974-04-18 | ADDITIVES FOR LUBRICANTS THEIR PREPARATION AND COMPOSITIONS THAT CONTAIN THEM |
| NL7405266A NL7405266A (en) | 1973-04-19 | 1974-04-18 | |
| JP49044348A JPS5918402B2 (en) | 1973-04-19 | 1974-04-18 | Manufacturing method for lubricating oil additives |
| BR3100/74A BR7403100D0 (en) | 1973-04-19 | 1974-04-18 | BIS- (REPLACED PHENOL) -CARBOXYL ACID STARCHES, PROCESS FOR ITS PREPARATION, LUBRICATING COMPOSITION, ADDITIVE CONCENTRATE AND ADDITIVE PACKAGE |
| DE2418760A DE2418760A1 (en) | 1973-04-19 | 1974-04-18 | NEW COMPOUNDS, PROCEDURES FOR THEIR PRODUCTION AND THEIR USE AS LUBRICANT ADDITIVES |
| ZA00742476A ZA742476B (en) | 1973-04-19 | 1974-04-18 | Lubricant additives,their preparation and compositions containing them |
| SE7405242D SE7405242L (en) | 1973-04-19 | 1974-04-18 | |
| AU68056/74A AU492069B2 (en) | 1973-04-19 | 1974-04-18 | Lubricant additives, their preparation and compositions containing them |
| AT320274A AT346309B (en) | 1973-04-19 | 1974-04-18 | METHOD FOR PRODUCING NEW BIS-PHENOLALKANIC ACID AMIDES |
| BE143378A BE813916A (en) | 1973-04-19 | 1974-04-18 | ADDITIVES FOR LUBRICANTS AND THEIR PREPARATION |
| FR7413462A FR2226416B1 (en) | 1973-04-19 | 1974-04-18 | |
| CH544574A CH605683A5 (en) | 1973-04-19 | 1974-04-19 | |
| CA198,657A CA1042454A (en) | 1973-04-19 | 1974-05-01 | Lubricant additives, their preparation and compositions containing them |
| US05/666,912 US4051049A (en) | 1973-04-19 | 1976-03-15 | Lubricating oil containing alkanoic amide or ester-bridged hydrocarbyl substituted phenols |
| AT517676A ATA517676A (en) | 1973-04-19 | 1976-07-14 | LUBRICANT COMPOSITION |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1917373A GB1459403A (en) | 1973-04-19 | 1973-04-19 | Lubricant additives their preparation and compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1459403A true GB1459403A (en) | 1976-12-22 |
Family
ID=10124960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1917373A Expired GB1459403A (en) | 1973-04-19 | 1973-04-19 | Lubricant additives their preparation and compositions containing them |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5918402B2 (en) |
| AR (1) | AR205535A1 (en) |
| AT (1) | AT346309B (en) |
| BE (1) | BE813916A (en) |
| BR (1) | BR7403100D0 (en) |
| CA (1) | CA1042454A (en) |
| CH (1) | CH605683A5 (en) |
| DE (1) | DE2418760A1 (en) |
| FR (1) | FR2226416B1 (en) |
| GB (1) | GB1459403A (en) |
| IT (1) | IT1012586B (en) |
| NL (1) | NL7405266A (en) |
| SE (1) | SE7405242L (en) |
| ZA (1) | ZA742476B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1713838B1 (en) | 2004-02-02 | 2018-08-15 | Basf Se | Method for producing polyisobutenylphenols |
-
1973
- 1973-04-19 GB GB1917373A patent/GB1459403A/en not_active Expired
-
1974
- 1974-01-01 AR AR253344A patent/AR205535A1/en active
- 1974-04-18 AT AT320274A patent/AT346309B/en not_active IP Right Cessation
- 1974-04-18 SE SE7405242D patent/SE7405242L/sv unknown
- 1974-04-18 FR FR7413462A patent/FR2226416B1/fr not_active Expired
- 1974-04-18 JP JP49044348A patent/JPS5918402B2/en not_active Expired
- 1974-04-18 DE DE2418760A patent/DE2418760A1/en not_active Ceased
- 1974-04-18 IT IT21642/74A patent/IT1012586B/en active
- 1974-04-18 BR BR3100/74A patent/BR7403100D0/en unknown
- 1974-04-18 ZA ZA00742476A patent/ZA742476B/en unknown
- 1974-04-18 BE BE143378A patent/BE813916A/en not_active IP Right Cessation
- 1974-04-18 NL NL7405266A patent/NL7405266A/xx not_active Application Discontinuation
- 1974-04-19 CH CH544574A patent/CH605683A5/xx not_active IP Right Cessation
- 1974-05-01 CA CA198,657A patent/CA1042454A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1713838B1 (en) | 2004-02-02 | 2018-08-15 | Basf Se | Method for producing polyisobutenylphenols |
Also Published As
| Publication number | Publication date |
|---|---|
| CH605683A5 (en) | 1978-10-13 |
| IT1012586B (en) | 1977-03-10 |
| AU6805674A (en) | 1975-10-23 |
| JPS5030905A (en) | 1975-03-27 |
| AR205535A1 (en) | 1976-05-14 |
| ATA320274A (en) | 1978-03-15 |
| JPS5918402B2 (en) | 1984-04-27 |
| AT346309B (en) | 1978-11-10 |
| FR2226416A1 (en) | 1974-11-15 |
| FR2226416B1 (en) | 1978-10-27 |
| CA1042454A (en) | 1978-11-14 |
| BR7403100D0 (en) | 1974-11-19 |
| SE7405242L (en) | 1974-10-21 |
| NL7405266A (en) | 1974-10-22 |
| BE813916A (en) | 1974-08-16 |
| ZA742476B (en) | 1975-12-31 |
| DE2418760A1 (en) | 1974-11-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |