US3010905A - Lubricating greases thickened with nitrophenylazo naphthol compounds - Google Patents
Lubricating greases thickened with nitrophenylazo naphthol compounds Download PDFInfo
- Publication number
- US3010905A US3010905A US826109A US82610959A US3010905A US 3010905 A US3010905 A US 3010905A US 826109 A US826109 A US 826109A US 82610959 A US82610959 A US 82610959A US 3010905 A US3010905 A US 3010905A
- Authority
- US
- United States
- Prior art keywords
- lubricating
- grease
- nitrophenylazo
- oil
- percent
- 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 - Lifetime
Links
- 230000001050 lubricating effect Effects 0.000 title claims description 21
- KABADTQADCBGSX-UHFFFAOYSA-N 3-nitro-2-phenyldiazenylnaphthalen-1-ol Chemical class Oc1c(N=Nc2ccccc2)c(cc2ccccc12)[N+]([O-])=O KABADTQADCBGSX-UHFFFAOYSA-N 0.000 title description 2
- 239000004519 grease Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000010687 lubricating oil Substances 0.000 claims description 11
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 239000002562 thickening agent Substances 0.000 description 10
- -1 2-methoxy-4-nitrophenylazo Chemical group 0.000 description 8
- 229920005573 silicon-containing polymer Polymers 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 230000008719 thickening Effects 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229950011260 betanaphthol Drugs 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 229920002545 silicone oil Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000010688 mineral lubricating oil Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XLTMWFMRJZDFFD-UHFFFAOYSA-N 1-[(2-chloro-4-nitrophenyl)diazenyl]naphthalen-2-ol Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl XLTMWFMRJZDFFD-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- QKKKXGIYBNNLCO-UHFFFAOYSA-N 1-[(2-methyl-4-nitrophenyl)diazenyl]naphthalen-2-ol Chemical compound CC1=C(C=CC(=C1)[N+](=O)[O-])N=NC1=C(C=CC2=CC=CC=C12)O QKKKXGIYBNNLCO-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- 241000231739 Rutilus rutilus Species 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229940067597 azelate Drugs 0.000 description 1
- HBHZKFOUIUMKHV-UHFFFAOYSA-N chembl1982121 Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HBHZKFOUIUMKHV-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LAQFLZHBVPULPL-UHFFFAOYSA-N methyl(phenyl)silicon Chemical compound C[Si]C1=CC=CC=C1 LAQFLZHBVPULPL-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- PWZUUYSISTUNDW-VAFBSOEGSA-N quinestrol Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@]4(O)C#C)C)CC2=CC=3OC1CCCC1 PWZUUYSISTUNDW-VAFBSOEGSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229940048098 sodium sarcosinate Drugs 0.000 description 1
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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
- C10M5/00—Solid or semi-solid compositions containing as the essential lubricating ingredient mineral lubricating oils or fatty oils and their use
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/14—Inorganic compounds or elements as ingredients in lubricant compositions inorganic compounds surface treated with organic compounds
-
- 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
-
- 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
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
-
- 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
-
- 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
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
-
- 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
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
-
- 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
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/066—Arylene diamines
-
- 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
- C10M2215/18—Containing nitrogen-to-nitrogen bonds, e.g. hydrazine
- C10M2215/182—Azo compounds
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- 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
-
- 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
-
- 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
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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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
- C10M2229/042—Siloxanes with specific structure containing aromatic substituents
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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
- C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double 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
- 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
- C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen 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
- 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
- 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
- C10M2229/051—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen
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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
Definitions
- This invention relates to improved lubricating greases, and more particularly to lubricating greases thickened with compounds of a class of high melting azo compounds.
- R is hydrogen, or a non-salt forming non-oil solubilizing substituent group, such as a lower aliphatic or lower alkoXy group, containing from 1 to about 3 carbon atoms, a nitro group, an amino group or a halogen.
- R is a methyl, methoxy or nitro group or a halogen.
- Suitable compounds of the above class include the following: l(4-nitr phenylazo)-2-naphthol; l (2-ch1oro-4-nitrophenylaz0) -2-naphthol; l (2,4-dinitrophenylazo) -2-naphthol; 1 (2-methyl-4-nitrophenylazo)-2- naphthol; l(2-methoxy-4-nitrophenylazo) -2-naphthol; and 1(2-amino-4-nitrophenylazo)-2-naphthol.
- These compounds are commercially available or readily obtainable by well known methods including coupling diazotized nitroanilines with Z-naphthol.
- the above compounds may be employed either in pure form or in the form of the so-called reduced toners, wherein the compounds are precipitated upon particles of inert inorganic materials such as SiO A1 T BaSO clay, etc.
- inert inorganic materials such as SiO A1 T BaSO clay, etc.
- such materials Will be presout only in minor amounts, such as up to about 10 percent by weight, but larger amounts up to about 25 percent by weight or higher, may be present if desired.
- the greases of this invention comprise essentially a lubricating oil as the major component containing sufficient amounts ofa thickening agent of the class described above to impart at least substantial thickening.
- the composition Will contain from about 10 to about 45 percent by weight of thickening agent of this type, and preferably about to about 40 percent by weight of such thickening agent, based on the weight of the composition.
- the grease preparation may be carried out by merely mixing together the thickener and any additives employed with the lubricating oil, employing any convenient means such as milling in a colloid mill or in a paint mill to obtain a thorough dispersion or thickener and additives in the lubricating oil base.
- the mixing may be carried out at ordinary temperatures or at elevated temperatures such as up to about 300 F. in order to dissolve any difiicultly soluble additives.
- the lubricating oils employed may be any suitable oils of lubricating characteristics, including the conventional a 3,010,905 ice Patented Nov. as, 19 1 mineral lubricating oils, synthetic oils obtained by various refinery processes such as cracking and polymerization, and other synthetic oleaginous compounds.
- suitable min-- eral oils include paraflinic and naphthenic oils having viscosities in the range from about seconds Saybolt Universal at 100 F. to about 225 seconds Saybolt Universal at 210 F., and preferably those having viscosities in the range from about 100 to about 600 seconds Saybolt Universal at 100 F.
- synthetic oils of various types, including particularly silicone oils and synthetic esters are preferably employed.
- Such oils may very advantageously comprise from about 50 up to 100 percent of the oil component of the grease, the remainder being mineral oil or other oil of a different type.
- Suitable synthetic esters include aliphatic diesters, such as di-2-ethylhexyl sebacate, di(secondary' amyl) sebacate, di-Z-ethylhexyl azelate, di-iso-o-ctyl adipate, etc.
- a particularly suitable class of synthetic esters are the polyesters described in US. 2,628,974, obtained by reacting an aliphatic dicarboxylic acid with a glycol and a monofunctional aliphatic alcohol or acid.
- Suitable silicone oils include, for example, dimethyl silicone polymer, diethyl silicone polymer, methylcyclohexyl silicone polymer, diphenylsilicone polymer, methylphenyl silicone polymer, methylethyl silicone polymer, methyltolyl silicone polymer, etc, preferably having viscosities in the range from about 100 to about 600 seconds Saybolt Universal at 100 F.
- Additives of the usual types may be employed in these greases, such as, for example, oxidation inhibitors, corrosion inhibitors, tackiness agents, extreme pressure agents, etc.
- Suitable oxidation inhibitors include particularly those of the amine type, such as diphenylamine, alpha-naphthylamine, beta-naphthylamine, para-phenylenediamine, and N,N'-diphenyl-p-phenylenediamine.
- Example I A lubricating grease representative of the greases of this invention is obtained by thickening a mineral lubrieating oil with 30 percent by weight, based on the weight of the composition of finely divided 1(2-chloro-4-nitrophenylazo)-2-naphthol.
- the latter is in the form of particles percent of which are in the 001 0.05 micron range and the remainder below 0.01 micron, in their largest dimension, and having a measured surface area of about '39 square meters per gram.
- This material is commercially available from the Hilton-Davis Chemical Company under the trade name of Flame Toner.
- the mineral lubricating oil is a refined naphthenic distillate oil having a Saybolt Universal viscosity at F. of about 330. p
- the grease preparation is carried out by mixing together the oil and thickener in the proportions disclosed above, employing an electric mixer, and passing the mixture through a Premier colloid mill with two passes at 0.002 inch clearance.
- the grease prepared as described above is a smooth N.L.G.I. No. 0 grade grease having a high dropping I 3 point and very superior lubricating properties generally as shown by the following test results:
- Example 11 Another grease representative of the greases of this invention is obtained by thickening a silicone polymer oil with 29.4 percent by weight of the solid thickener described in Example I.
- the silicone oil is a methylchlorophenyl silicone oil, sold by the General Electric Company under the tradename of Versilube F-SO. Typical inspection tests upon this oil include molecular weight of 2760, a silicone content of 33.6 percent and a chlorine content of 7.2 percent.
- the grease also contains 1.0 percent by weight of acommercial rust inhibitor, which is a reaction product of sodium sarcosinate with coconut oil fatty acid chlorides. The grease preparation is carried out as de scribed in Example I.
- the grease prepared as described above is a smooth N.L.G.I; No. 2 grade grease having a high dropping point and very superior lubricating properties generally as shown by the following test results:
- Another grease representative or the greases of this invention is obtained by employing finely divided 1(2- methoxy-4-nitrophenylazo)-2-naphtho1, having a particle size below 0.05 micron, as the thickening agent in a synthetic ester oil.
- the latter is a product obtained by react.- ing sebacic acid, 2-ethylhexane-1,3-dio l and Z-ethylhexanol in about a 2:1:1 ratio respectively, and consisting predominantly of the compound ployed in accordance with this invention were found to have only a very low thickening action in lubricating oils, which was insufficient to form greases.
- a lubricating grease consisting essentially of a lubricating oil as the major component thickened to a grease consistency with a compound having the formula wherein R is chosen from the group consisting of hydrogen, lower aliphatic groups and lower alkoxy groups containing 1-3 carbon atoms, the nitro group, amino groups and halogens.
- a lubricating grease consisting essentially of a mineral lubricating oil thickened to a grease consistency with about 2040 percent by Weight of 1(2-chloro-4-nitrophenylazo)-2-naphthol in finely divided form.
- a lubricating grease according to claim 8 containing about 0.55 percent of an amine oxidation inhibitor.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
3,010,905 LUBRICATING GREASES TEHCKENED WITH NI- TROPFENYLAZO NAPHTHOL COMPOUNDS Norman R. Odell, Fishkill, and Joseph F. Lyons, Foughkeepsie, N.Y., assignors to Texaco Inc., New York, N.Y., a corporation of Delaware No Drawing. Filed July 10, 1959, Ser. No. 826,109
10 Claims. (Cl. 252-515) This invention relates to improved lubricating greases, and more particularly to lubricating greases thickened with compounds of a class of high melting azo compounds.
We have found that compounds of a class of nitrophenylazo naphthols have the property of thickening lubricating oils to a grease-like consistency when they are dispersed therein in finely divided form, and that the greases thus produced have unexpectedly superior lubricating properties, including particularly the combination of exceptional oxidation resistance and water solubility.
The compounds which are employed as grease thickening agents in accordance with this invention are represented by the general formula wherein R is hydrogen, or a non-salt forming non-oil solubilizing substituent group, such as a lower aliphatic or lower alkoXy group, containing from 1 to about 3 carbon atoms, a nitro group, an amino group or a halogen. The preferred compounds are those wherein R is a methyl, methoxy or nitro group or a halogen.
Examples of suitable compounds of the above class include the following: l(4-nitr phenylazo)-2-naphthol; l (2-ch1oro-4-nitrophenylaz0) -2-naphthol; l (2,4-dinitrophenylazo) -2-naphthol; 1 (2-methyl-4-nitrophenylazo)-2- naphthol; l(2-methoxy-4-nitrophenylazo) -2-naphthol; and 1(2-amino-4-nitrophenylazo)-2-naphthol. These compounds are commercially available or readily obtainable by well known methods including coupling diazotized nitroanilines with Z-naphthol.
The above compounds may be employed either in pure form or in the form of the so-called reduced toners, wherein the compounds are precipitated upon particles of inert inorganic materials such as SiO A1 T BaSO clay, etc. Generally such materials Will be presout only in minor amounts, such as up to about 10 percent by weight, but larger amounts up to about 25 percent by weight or higher, may be present if desired.
The greases of this invention comprise essentially a lubricating oil as the major component containing sufficient amounts ofa thickening agent of the class described above to impart at least substantial thickening. Ordinarily the composition Will contain from about 10 to about 45 percent by weight of thickening agent of this type, and preferably about to about 40 percent by weight of such thickening agent, based on the weight of the composition.
The grease preparation may be carried out by merely mixing together the thickener and any additives employed with the lubricating oil, employing any convenient means such as milling in a colloid mill or in a paint mill to obtain a thorough dispersion or thickener and additives in the lubricating oil base. The mixing may be carried out at ordinary temperatures or at elevated temperatures such as up to about 300 F. in order to dissolve any difiicultly soluble additives.
The lubricating oils employed may be any suitable oils of lubricating characteristics, including the conventional a 3,010,905 ice Patented Nov. as, 19 1 mineral lubricating oils, synthetic oils obtained by various refinery processes such as cracking and polymerization, and other synthetic oleaginous compounds. Suitable min-- eral oils include paraflinic and naphthenic oils having viscosities in the range from about seconds Saybolt Universal at 100 F. to about 225 seconds Saybolt Universal at 210 F., and preferably those having viscosities in the range from about 100 to about 600 seconds Saybolt Universal at 100 F. For preparing high temperature greases, synthetic oils of various types, including particularly silicone oils and synthetic esters are preferably employed. Such oils may very advantageously comprise from about 50 up to 100 percent of the oil component of the grease, the remainder being mineral oil or other oil of a different type. Suitable synthetic esters include aliphatic diesters, such as di-2-ethylhexyl sebacate, di(secondary' amyl) sebacate, di-Z-ethylhexyl azelate, di-iso-o-ctyl adipate, etc. A particularly suitable class of synthetic esters are the polyesters described in US. 2,628,974, obtained by reacting an aliphatic dicarboxylic acid with a glycol and a monofunctional aliphatic alcohol or acid. Suitable silicone oils include, for example, dimethyl silicone polymer, diethyl silicone polymer, methylcyclohexyl silicone polymer, diphenylsilicone polymer, methylphenyl silicone polymer, methylethyl silicone polymer, methyltolyl silicone polymer, etc, preferably having viscosities in the range from about 100 to about 600 seconds Saybolt Universal at 100 F.
Additives of the usual types may be employed in these greases, such as, for example, oxidation inhibitors, corrosion inhibitors, tackiness agents, extreme pressure agents, etc. Suitable oxidation inhibitors include particularly those of the amine type, such as diphenylamine, alpha-naphthylamine, beta-naphthylamine, para-phenylenediamine, and N,N'-diphenyl-p-phenylenediamine. A
solids of various types and metal soaps of high molecular Weight fatty acids such as are commonly employed as thickening agents in lubricating greases.
The following examples are given for the purpose of further dis-closing the invention.
Example I A lubricating grease representative of the greases of this invention is obtained by thickening a mineral lubrieating oil with 30 percent by weight, based on the weight of the composition of finely divided 1(2-chloro-4-nitrophenylazo)-2-naphthol. The latter is in the form of particles percent of which are in the 001 0.05 micron range and the remainder below 0.01 micron, in their largest dimension, and having a measured surface area of about '39 square meters per gram. This material is commercially available from the Hilton-Davis Chemical Company under the trade name of Flame Toner.
The mineral lubricating oil is a refined naphthenic distillate oil having a Saybolt Universal viscosity at F. of about 330. p
The grease preparation is carried out by mixing together the oil and thickener in the proportions disclosed above, employing an electric mixer, and passing the mixture through a Premier colloid mill with two passes at 0.002 inch clearance.
The grease prepared as described above is a smooth N.L.G.I. No. 0 grade grease having a high dropping I 3 point and very superior lubricating properties generally as shown by the following test results:
lbs. pressure drop ;s A Dynamic water resistance, percent loss Water absorption, percent e e 50 li'enetration before test 337 Penetration after test 295 1 Unw'orlted, converted from size cone.
Example 11 Another grease representative of the greases of this invention is obtained by thickening a silicone polymer oil with 29.4 percent by weight of the solid thickener described in Example I. The silicone oil is a methylchlorophenyl silicone oil, sold by the General Electric Company under the tradename of Versilube F-SO. Typical inspection tests upon this oil include molecular weight of 2760, a silicone content of 33.6 percent and a chlorine content of 7.2 percent. The grease also contains 1.0 percent by weight of acommercial rust inhibitor, which is a reaction product of sodium sarcosinate with coconut oil fatty acid chlorides. The grease preparation is carried out as de scribed in Example I.
The grease prepared as described above is a smooth N.L.G.I; No. 2 grade grease having a high dropping point and very superior lubricating properties generally as shown by the following test results:
Dropping point, F 411 ASTM penetration at 77 F.:
Unworked 247 Worked, 60 strokes 270 Worked, 100,000 strokes 295 ASTM bomb oxidation test (100 hrs. at 250 F.),
' lbs. pressure drop 2 Dynamic water resistance, percent loss 0 CRC bearing protection test Pass Another grease representative or the greases of this invention is obtained by employing finely divided 1(2- methoxy-4-nitrophenylazo)-2-naphtho1, having a particle size below 0.05 micron, as the thickening agent in a synthetic ester oil. The latter is a product obtained by react.- ing sebacic acid, 2-ethylhexane-1,3-dio l and Z-ethylhexanol in about a 2:1:1 ratio respectively, and consisting predominantly of the compound ployed in accordance with this invention were found to have only a very low thickening action in lubricating oils, which was insufficient to form greases.
Obviously many modifications and variations of the invention, as hereinbefore set forth, may be made without departing from the spirit and scope thereof and only such limitations should be imposed as are indicated in the appended claims.
We claim:
1. A lubricating grease consisting essentially of a lubricating oil as the major component thickened to a grease consistency with a compound having the formula wherein R is chosen from the group consisting of hydrogen, lower aliphatic groups and lower alkoxy groups containing 1-3 carbon atoms, the nitro group, amino groups and halogens.
2. A lubricating composition according to claim 1 wherein the said lubricating oil is a mineral oil.
3. A lubricating grease according to claim 1 wherein the said lubricating oil is a dicarboxylic acid ester.
4. A lubricating grease according to claim 1 wherein the said R substituent is a nitro group.
. S. A lubricating grease according to claim 1 wherein the said R substituent is a methyl group.
, 6. A lubricating grease according to claim 1 wherein the said R substituent is a methoxy group.
7. A lubricating grease according to claim 1 wherein the said R substituent is chlorine.
8. A lubricating grease consisting essentially of a mineral lubricating oil thickened to a grease consistency with about 2040 percent by Weight of 1(2-chloro-4-nitrophenylazo)-2-naphthol in finely divided form.
9. A lubricating grease according to claim 8 wherein the said lubricating oil is an aliphatic dicarboxylic acid polyester.
10. A lubricating grease according to claim 8 containing about 0.55 percent of an amine oxidation inhibitor.
References Cited in the tile of this patent UNITED STATES PATENTS 2,679,480 Brannen et a1; May 25, 1954 2,848,417 Armstrong et al Aug. 19, 1958 2,880,176 Roach et a1 Mar. 31, 1959 2,880,177 Lyons et a1. Mar. 31, 1959 2,915,470 Armstrong et a1. Dec. 1, 1959 UNITED STATES PATENT. OFFICE CERTIFICATE OF CORRECTION Patent N0. 3,010,905 November- 28, 1961 Norman Re Odell et 211..
It is hereby certified that error appears in the above Dumbered patent requiring correction and that the said Letters Patent should ,read as corrected below.
Column 1 line 20, solubility read stability Signed and sealed this 17th day of April 1962.
(SEAL) Attest: ESTON c. JOHNSON DAVID L. LADD Attesting Officer Commissioner of Patents
Claims (1)
1. A LUBRICATING GREASE CONSISTING ESSENTIALLY OF A LUBRICATING OIL AS THE MAJOR COMPONENT THICKENED TO A GREASE CONSISTENCY WITH A COMPOUND HAVING THE FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US826109A US3010905A (en) | 1959-07-10 | 1959-07-10 | Lubricating greases thickened with nitrophenylazo naphthol compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US826109A US3010905A (en) | 1959-07-10 | 1959-07-10 | Lubricating greases thickened with nitrophenylazo naphthol compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3010905A true US3010905A (en) | 1961-11-28 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US826109A Expired - Lifetime US3010905A (en) | 1959-07-10 | 1959-07-10 | Lubricating greases thickened with nitrophenylazo naphthol compounds |
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| Country | Link |
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| US (1) | US3010905A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3346491A (en) * | 1965-06-08 | 1967-10-10 | Mobil Oil Corp | Polyazophenols and polyazophenol greases |
| US3378491A (en) * | 1966-02-18 | 1968-04-16 | Mobil Oil Corp | Stabilized organic compositions |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2679480A (en) * | 1952-11-01 | 1954-05-25 | Standard Oil Co | Indogen thickened grease composition |
| US2848417A (en) * | 1955-08-15 | 1958-08-19 | Shell Dev | Extreme high temperature grease compositions |
| US2880176A (en) * | 1956-12-24 | 1959-03-31 | Texas Co | Lubricating grease comprising methylchlorophenyl silicone polymer thickened with a high melting diazo compound |
| US2880177A (en) * | 1956-12-28 | 1959-03-31 | Texas Co | Lubricating greases thickened with benzidine diazo compounds |
| US2915470A (en) * | 1957-12-16 | 1959-12-01 | Shell Dev | Grease manufacturing process for pigment or dye gelled oils |
-
1959
- 1959-07-10 US US826109A patent/US3010905A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2679480A (en) * | 1952-11-01 | 1954-05-25 | Standard Oil Co | Indogen thickened grease composition |
| US2848417A (en) * | 1955-08-15 | 1958-08-19 | Shell Dev | Extreme high temperature grease compositions |
| US2880176A (en) * | 1956-12-24 | 1959-03-31 | Texas Co | Lubricating grease comprising methylchlorophenyl silicone polymer thickened with a high melting diazo compound |
| US2880177A (en) * | 1956-12-28 | 1959-03-31 | Texas Co | Lubricating greases thickened with benzidine diazo compounds |
| US2915470A (en) * | 1957-12-16 | 1959-12-01 | Shell Dev | Grease manufacturing process for pigment or dye gelled oils |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3346491A (en) * | 1965-06-08 | 1967-10-10 | Mobil Oil Corp | Polyazophenols and polyazophenol greases |
| US3378491A (en) * | 1966-02-18 | 1968-04-16 | Mobil Oil Corp | Stabilized organic compositions |
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