US3870642A - Grease thickened with oxygen-linked polyureas - Google Patents
Grease thickened with oxygen-linked polyureas Download PDFInfo
- Publication number
- 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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- Prior art keywords
- monoamino
- carbon atoms
- isocyanate
- mixture
- process according
- Prior art date
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Classifications
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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
- C10M119/00—Lubricating compositions characterised by the thickener being a macromolecular compound
- C10M119/24—Lubricating compositions characterised by the thickener being a macromolecular compound containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing compounds
- C08G18/2865—Compounds having only one primary or secondary amino group; Ammonia
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
- C08G18/808—Monoamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/02—Polyureas
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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
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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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
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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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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- 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
- C10M2207/283—Esters of polyhydroxy compounds
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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
- C10M2207/286—Esters of polymerised unsaturated acids
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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
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
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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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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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
- 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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- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/10—Amides of carbonic or haloformic acids
- C10M2215/102—Ureas; Semicarbazides; Allophanates
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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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- 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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- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- 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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- 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
- C10M2229/02—Unspecified siloxanes; Silicones
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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
- 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
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/02—Bearings
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- 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—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
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- 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
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)
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;«*« |
Publications (1)
Publication Number | Publication Date |
---|---|
US3870642A true US3870642A (en) | 1975-03-11 |
Family
ID=5864057
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US420004A Expired - Lifetime US3870642A (en) | 1972-12-11 | 1973-11-29 | Grease thickened with oxygen-linked polyureas |
Country Status (6)
Country | Link |
---|---|
US (1) | US3870642A (enrdf_load_html_response) |
JP (1) | JPS49102708A (enrdf_load_html_response) |
DE (1) | DE2260496C3 (enrdf_load_html_response) |
FR (1) | FR2209831B1 (enrdf_load_html_response) |
GB (1) | GB1406553A (enrdf_load_html_response) |
NL (1) | NL7316855A (enrdf_load_html_response) |
Cited By (8)
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)
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)
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 |
-
1972
- 1972-12-11 DE DE2260496A patent/DE2260496C3/de not_active Expired
-
1973
- 1973-11-23 GB GB5446073A patent/GB1406553A/en not_active Expired
- 1973-11-29 US US420004A patent/US3870642A/en not_active Expired - Lifetime
- 1973-12-08 JP JP48137619A patent/JPS49102708A/ja active Pending
- 1973-12-10 FR FR7343980A patent/FR2209831B1/fr not_active Expired
- 1973-12-10 NL NL7316855A patent/NL7316855A/xx not_active Application Discontinuation
Patent Citations (3)
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)
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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