US3870642A - Grease thickened with oxygen-linked polyureas - Google Patents

Grease thickened with oxygen-linked polyureas Download PDF

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US3870642A
US3870642A US420004A US42000473A US3870642A US 3870642 A US3870642 A US 3870642A US 420004 A US420004 A US 420004A US 42000473 A US42000473 A US 42000473A US 3870642 A US3870642 A US 3870642A
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monoamino
carbon atoms
isocyanate
mixture
process according
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Eberhard Gegner
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BP PLC
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BP PLC
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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
    • C10M119/00Lubricating compositions characterised by the thickener being a macromolecular compound
    • C10M119/24Lubricating compositions characterised by the thickener being a macromolecular compound containing nitrogen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805Compounds having only one group containing active hydrogen
    • C08G18/285Nitrogen containing compounds
    • C08G18/2865Compounds having only one primary or secondary amino group; Ammonia
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/32Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225Polyamines
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/80Masked polyisocyanates
    • C08G18/8061Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C08G18/808Monoamines
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/02Polyureas
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/281Esters of (cyclo)aliphatic monocarboxylic acids
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    • 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
    • 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
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/283Esters of polyhydroxy compounds
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/286Esters of polymerised unsaturated acids
    • 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
    • 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
    • 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
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • 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
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • 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
    • 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
    • C10M2215/042Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • 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
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/10Amides of carbonic or haloformic acids
    • C10M2215/102Ureas; Semicarbazides; Allophanates
    • 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
    • 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
    • C10M2217/042Macromolecular 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
    • 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
    • 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
    • C10M2217/043Mannich bases
    • 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
    • C10M2229/00Organic 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
    • C10M2229/02Unspecified siloxanes; Silicones
    • 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
    • C10M2229/00Organic 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
    • C10M2229/04Siloxanes with specific structure
    • C10M2229/05Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/02Bearings
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00Specific manufacturing methods for lubricant compositions

Definitions

  • Greases in accordance with US. Pat. No. 3 243 372 are produced by dissolving a di-isocyanate in the lubricating oil which is to be thickened, optionally by making use of a further solvent, adding amines to this mixture and then heating the total mixture, the polyurea being formed in situ.
  • Greases with polyureas as thickeners are chemically resistant to water and oxidation; they decompose under the action of heat only at relatively high temperatures.
  • Greases with such polyureas as thickeners are chemically resistant to water, oxidation and the action of heat; they also possess good load-bearing capacity and mechanical stability. Furthermore they are distinguished by a reduced tendency to gel or harden.
  • a process for the production of a polyurea which process comprises reacting a monoamino, a diamino and a di-isocyanate component at a temperature in the range 20 to lC wherein a. the monoamino component comprises a mixture of at least two members selected from different groups of general formulae:
  • R is a monovalent aliphatic radical containing 12 to 24 carbon atoms
  • R2 is a monovalent aromatic radical
  • R is a monovalent aliphatic radical containing 2 to 10 carbon atoms
  • R is a divalent aliphatic radical containing 2 to 4 carbon atoms
  • the diamino component comprises a dioxa-alkane diamine or a mixture of dioxa-alkanediamines of general formula:
  • R and R are divalent aliphatic radicals containing 2 to 4 carbon atoms and R is a divalent aliphatic radical containing 2 to 10 carbon atoms
  • the di-isocyanate component comprises an aromatic di-isocyanate or a mixture of aromatic diisocyanates.
  • a process for the production of a grease which process comprises reacting a monoamino, a diamino and a di-isocyanate component in a lubricating oil at a temperature in the range 20to 150C wherein (a) the monoamino component comprises a mixture of at least two members selected from different groups of general formulae:
  • R is a monovalent aliphatic radical containing 12 to 24 carbon atoms
  • R is a monovalent aromatic radical
  • R is a monovalent aliphatic radical containing 2 to 10 carbon atoms
  • R is a divalent aliphatic radical containing 2 to 4 carbon atoms.
  • the diamino component comprises a dioxaalkanediamine or a mixture of dioxa-alkanediamines of general formula:
  • R and R are divalent aliphatic radicals containing 2 to 4 carbon atoms, and R is a divalent aliphatic radical containing 2 to 10 carbon atoms, and
  • the di-isocyanate component comprises an aromatic di-isocyanate or a mixture of aromatic diisocyanates.
  • the components are preferably reacted at a temperature of in the range 40 to C.
  • reaction mixture is then heated further to a temperature of to 200C, preferably to about C.
  • a temperature of to 200C preferably to about C.
  • the di-isocyanate component optionally at a temperature which is above its melting point, or dissolved in lubricating oil or in a solvent which is inert under the reaction conditions, is added to the mixture of mono-amino and diamino components and the lubricating oil.
  • the di-isocyanate component is thus exposed during the reaction to an excess of amines, as a result of which the degree of branching or cross-linking il'lZCll oin several atpha ac menwamineethens: astnoaw -.rminoi :eornpeaenit; :the compounds .c otresp mane menarmino coanponerat; :the :eornpoands correspondi g Q -:tlre molar ratio of; a1
  • the molar ratio of aliphatic mono-amine or mono-amines to aromatic mono-amines or mono-amines to aliphatic monoamino-ether or aliphatic mono-amino-ethers is preferably about l:O.5:O.5.
  • the aliphatic mono-amine in the mono-amino component is preferably a straight-chained monoamine with 16 to 24 carbon atoms per molecule, or a mixture of such mono-amines.
  • the aromatic mono-amine in the mono-amino component is preferably aniline, toluidine or xylidine or a mixture of these amines. isomeric aromatic monoamines can be used individually or as an isomer mixture.
  • the aliphatic mono-amino-ether of the general formula is preferably one in which R is a monovalent aliphatic radical containing 4 to 6 carbon atoms and R is a divalent aliphatic radical containing 2 or 3 carbon atoms. These mono-amino-ethers can be used separately or as mixtures.
  • the dioxa-alkanediamine of the general formula is preferably one in which R and R are divalent alialiphatic: monmatnine or; sev r l; an phatie' ntone-amines and :aln aroirniatiic: mono amine: or
  • Desmodur T mixture of 65% 2,4-toluylene di-isocyanate and 35% 2,6-toluylene dioisocyanate
  • H water
  • a further g of the same base oil was added to the feed vessel for the di-isocyanates.
  • the reaction mixture was then heated with further stirring to C, and when this temperature was reached the mixture was cooled to 100C.
  • a mixture of 10 g of Amine T corrosion inhibitor by Ciba-Geigy).
  • Additin 30 oxidation inhibitor by Wegriken Buyer
  • 2 g Reomet SBT metal de-activator by Ciba-Geigyi and 168 g base oil were then added and the mixture stirred until cold. When cold the grease was homoge' nised in a colloid mill.
  • Corrosion index according to Emcor Test B run (1,500 r.p.m., 130C) passed (DlN 51 802) 0 Oil separation (1P 121/63) 2.1% by wt. Mechanical/Dynamic SKF test (DIN 51 806): A run (2,500 r.p.m. without heating) passed B run (1,500 r.p.m. at 130C) passed EXAMPLE 2 A mixture of 41.5 g.
  • reaction mixture was then heated with further stirring to 175C, and after reaching this temperature the mixture was cooled to 100C.
  • a mixture of 10 g of Amine T, g of Additin 30, 2 g of Reomet SBT and 168 of base oil was then added, and the mixture stirred until cold. When cold the grease was homogenised in a colloid mill.
  • EXAMPLE 4 A mixture of 40.1 gv of 4,9-dioxadodecane-l .12- diamine, 60.3 g of Genamin 20/22 R D, 31.2 g of hexyloxy-propylamine and 1,500 g of a mixed-base solvent raffinate (l4E/50C corresponding to est/50C) was heated to 60C with stirring. The amines formed a clear solution with the mineral oil at this temperature. Maintaining constant intensive stirring, 68.4 g of Desmodur T 65 were added dropwise over 10 minutes. The turbidity which set in immediately increased rapidly and the contents of the reactor thickened.
  • a mixed-base solvent raffinate l4E/50C corresponding to est/50C
  • the molar ratio of the reaction components was 1 l :1 :2.
  • a process for the production of a grease which process comprises reacting a monoamino, a diamino and a di-isocyanate component in a lubricating oil at a temperature in the range 20to C wherein a. the monoamino component comprises a mixture of at least two members selected from different groups of general forumulae:
  • the diamino component comprises a dioxaalkanediaminc or a mixture of dioxaalkancdiamincs of general formula:
  • R and R are divalent aliphatic radicals containing 2 to 4 carbon atoms, and R is a divialent aliphatic radical containing 2 to 10 carbon atoms, and
  • the di-isocyanate component comprises an aromatic di-isocyanate or a mixture of aromatic diisoeyanates wherein the molar ratio between monoamino, diamino and di isocyanate components is in the range of 2:1:2 to 2:2:3.75.
  • reaction mixture is subsequently heated to a temperature in the range 150 to 200C.
  • a process according to claim l wherein the molar ratio between monoamino, diamino and di-isocyanate components is in the range 2:112 to 211:2.5.
  • the monoamino component comprises a monoamine of general formula R -NH in which R is a monovalent aliphatic radical containing 16 to 24 carbon atoms.
  • the monoamino component comprises an aromatic monoamine which is aniline, toluidine. xylidine. or a mixture thereof.
  • the monoamino component comprises a monoamine of general formula R O-R*NH in which R is a monovalent aliphatic radical containing 4 to 6 carbon atoms and R is a divalent aliphatic radical containing 1 or 3 carbon atoms.
  • diamino component comprises a straight chain dioxa-alkane diamine of general formula NH -R"O--R OR- l ll-i in which R and R are divalent aliphatic radicals containing 2 or 3 carbon atoms and R is a divalent aliphatic radical containing 4 to 6 carbon atoms.
  • a process according to claim 1 wherein the diisocyanate component comprises phenylene, toluyleneditolylene-, naphthylene. or diphenylmethane diisocyanate, or mixtures thereof.
  • the lubrieating oil is a mineral oil, a polyaryl ether. 21 polyalkylene glycol. a polysiloxane or an ester.
  • the mineral lubricating oil is a paraffinic or naphthenic lubricating oil fraction or a mixture thereof.
  • a grease composition comprising a lubricating oil thickened by 3-30% by weight of a polyurea formed in situ, said composition being formed by a process which comprises reacting a monoamino component and a diamino component with a di-isocyanate component in a lubricating oil at a temperature in the range 20to C wherein a. the monoamino component comprises a mixture ol at least two members selected from the following general formulae:
  • R is a monovalent aliphatic radical containing 12 to 24 carbon atoms
  • R is a monovalent aromatic radical
  • R is a monovalent aliphatic radical containing 2 to 10 carbon atoms
  • R" is a divalent aliphatic radical containing 2 to 4 carbon atoms
  • the diamino component comprises a dioxa-alkane diamine or a mixture of dioxa-alkanediamines of the general formula: NH R --OR-OR- NH in which R and R are divalent aliphatic radicals containing 2 to 4 carbon atoms and R is a divalent aliphatic radical containing 2 to 10 carbon atoms, and
  • the di-isocyanate component comprises an aromatic di-isocyanate or a mixture of aromatic di' isocyanates wherein the molar ratio of the monoamino, diamino and di-isocyanate components is in the range of 2:132 to 21213.75.
  • composition of claim 18 wherein the molar ratio between monoamino, diamino and di-isocyanate components is in the range 2:1:2 to 2:l:2.5.
  • composition of claim 18 wherein the molar ratio between monoamino, diamino and di-isocyanate components is in the range 2:2:3.75.
  • composition of claim 18 wherein the monoamino component comprises a monoamine of the general formula RNH in which R is a monovalent aliphatic radical containing 16 to 24 carbon atoms.
  • composition of claim 18 wherein the monoamino component comprises an aromatic monoamine which is aniline. toluidine, xylidine, or a mixture thereof.
  • composition of claim 18 wherein the monoamino component comprises a monoamine of the general formula R O-RNH in which R is a monovalent aliphatic radical containing 4 to 6 carbon atoms and R is a divalent aliphatic radical containing 2 or 3 carbon atoms.
  • composition of claim 18 wherein the diamino component comprises a straight chain dioxa-alkane diamine of the general formula NH R"O-R- "'O-R NH in which R and R are divalent aliphatic radicals containing 2 or 3 carbon atoms and R is a divalent aliphatic radical containing 4 to 6 carbon atoms.
  • composition of claim 18 wherein the reaction is carried out at a temperature in the range 40 to C.
  • composition of claim 18 wherein the reaction mixture is subsequently heated to a temperature in the range to 200C.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Polyurethanes Or Polyureas (AREA)
US420004A 1972-12-11 1973-11-29 Grease thickened with oxygen-linked polyureas Expired - Lifetime US3870642A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2260496A DE2260496C3 (de) 1972-12-11 1972-12-11 Schmierfette sowie Verfahren zu ihrer Herste;«*«

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US3870642A true US3870642A (en) 1975-03-11

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JP (1) JPS49102708A (enrdf_load_html_response)
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4129512A (en) * 1976-02-05 1978-12-12 The British Petroleum Company Limited Lubricating greases
US4261845A (en) * 1980-01-18 1981-04-14 Texaco Development Corporation Novel polyureas and their use as grease thickening agents
US4668411A (en) * 1984-12-27 1987-05-26 Koyo Seiko Co., Ltd. Diurea type grease composition
US5554586A (en) * 1995-02-27 1996-09-10 Texaco Inc. Polyurea thickener and grease composition
US20040167045A1 (en) * 2003-02-20 2004-08-26 Ward Carl E. Low noise grease gelling agents
US12091580B2 (en) 2019-02-15 2024-09-17 Kansai Paint Co., Ltd. Paint composition
US12240997B2 (en) 2019-02-15 2025-03-04 Kansai Paint Co., Ltd. Rheology control agent and paint composition
US12378423B2 (en) 2019-03-26 2025-08-05 Kansai Paint Co., Ltd. Paint composition

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3920571A (en) * 1974-09-16 1975-11-18 Chevron Res Grease composition and method of preparing the same
DE2604342A1 (de) * 1976-02-05 1977-08-18 Bp Benzin Und Petroleum Ag Polyharnstoff-schmierfette und verfahren zu ihrer herstellung
GB2237277A (en) * 1989-10-26 1991-05-01 Ici Plc Thixotropic binder system
DE102004039157A1 (de) * 2004-08-11 2006-02-23 Rhein Chemie Rheinau Gmbh Verfahren zur Herstellung pulverförmiger Polyharnstoffe mittels Sprühtrocknung
DE102004039156A1 (de) * 2004-08-11 2006-02-23 Rhein Chemie Rheinau Gmbh Verfahren zur Herstellung pulverförmiger Polyharnstoffe

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3243372A (en) * 1961-01-24 1966-03-29 Chevron Res Greases thickened with polyurea
US3374170A (en) * 1966-04-04 1968-03-19 Gulf Research Development Co Grease composition
US3725279A (en) * 1970-08-12 1973-04-03 Mobil Oil Corp Polyurea thickened grease

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3243372A (en) * 1961-01-24 1966-03-29 Chevron Res Greases thickened with polyurea
US3374170A (en) * 1966-04-04 1968-03-19 Gulf Research Development Co Grease composition
US3725279A (en) * 1970-08-12 1973-04-03 Mobil Oil Corp Polyurea thickened grease

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4129512A (en) * 1976-02-05 1978-12-12 The British Petroleum Company Limited Lubricating greases
US4261845A (en) * 1980-01-18 1981-04-14 Texaco Development Corporation Novel polyureas and their use as grease thickening agents
US4668411A (en) * 1984-12-27 1987-05-26 Koyo Seiko Co., Ltd. Diurea type grease composition
US5554586A (en) * 1995-02-27 1996-09-10 Texaco Inc. Polyurea thickener and grease composition
US20040167045A1 (en) * 2003-02-20 2004-08-26 Ward Carl E. Low noise grease gelling agents
US6916768B2 (en) 2003-02-20 2005-07-12 Chevron U.S.A. Inc. Low noise grease gelling agents
US12091580B2 (en) 2019-02-15 2024-09-17 Kansai Paint Co., Ltd. Paint composition
US12240997B2 (en) 2019-02-15 2025-03-04 Kansai Paint Co., Ltd. Rheology control agent and paint composition
US12378423B2 (en) 2019-03-26 2025-08-05 Kansai Paint Co., Ltd. Paint composition

Also Published As

Publication number Publication date
DE2260496B2 (de) 1978-10-05
DE2260496C3 (de) 1979-06-07
NL7316855A (enrdf_load_html_response) 1974-06-13
JPS49102708A (enrdf_load_html_response) 1974-09-27
FR2209831A1 (enrdf_load_html_response) 1974-07-05
FR2209831B1 (enrdf_load_html_response) 1978-11-10
GB1406553A (en) 1975-09-17
DE2260496A1 (de) 1974-07-04

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