US3773668A - Lubricating compositions - Google Patents
Lubricating compositions Download PDFInfo
- Publication number
- US3773668A US3773668A US00204329A US3773668DA US3773668A US 3773668 A US3773668 A US 3773668A US 00204329 A US00204329 A US 00204329A US 3773668D A US3773668D A US 3773668DA US 3773668 A US3773668 A US 3773668A
- Authority
- US
- United States
- Prior art keywords
- carbon atoms
- oils
- ether
- percent
- esters
- 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
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- 239000000203 mixture Substances 0.000 title claims abstract description 38
- 230000001050 lubricating effect Effects 0.000 title claims abstract description 14
- 150000002148 esters Chemical class 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- 238000009833 condensation Methods 0.000 claims description 15
- 230000005494 condensation Effects 0.000 claims description 15
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 12
- 229920001451 polypropylene glycol Polymers 0.000 claims description 10
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 9
- 230000032050 esterification Effects 0.000 claims description 8
- 238000005886 esterification reaction Methods 0.000 claims description 8
- 229920005862 polyol Polymers 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 5
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- -1 aliphatic polyols Chemical class 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 26
- 229930195733 hydrocarbon Natural products 0.000 abstract description 24
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 20
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 12
- 238000000034 method Methods 0.000 abstract description 11
- 229920001521 polyalkylene glycol ether Polymers 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000012530 fluid Substances 0.000 abstract description 4
- 239000010730 cutting oil Substances 0.000 abstract description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 26
- 229910052500 inorganic mineral Inorganic materials 0.000 description 11
- 239000011707 mineral Substances 0.000 description 11
- 235000010755 mineral Nutrition 0.000 description 11
- 239000000654 additive Substances 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 229920001515 polyalkylene glycol Polymers 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-L dodecanedioate(2-) Chemical compound [O-]C(=O)CCCCCCCCCCC([O-])=O TVIDDXQYHWJXFK-UHFFFAOYSA-L 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229940117969 neopentyl glycol Drugs 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003606 oligomerizing effect Effects 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PIMNDJYXVOQVSP-UHFFFAOYSA-N 1-o-ethyl 10-o-hexyl decanedioate Chemical compound CCCCCCOC(=O)CCCCCCCCC(=O)OCC PIMNDJYXVOQVSP-UHFFFAOYSA-N 0.000 description 1
- KDMAJIXYCNOVJB-UHFFFAOYSA-N 2,2-bis(nonanoyloxymethyl)butyl nonanoate Chemical compound CCCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCCC)COC(=O)CCCCCCCC KDMAJIXYCNOVJB-UHFFFAOYSA-N 0.000 description 1
- YRIMSXJXBHUHJT-UHFFFAOYSA-N 2,3-di(nonanoyloxy)propyl nonanoate Chemical compound CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC)COC(=O)CCCCCCCC YRIMSXJXBHUHJT-UHFFFAOYSA-N 0.000 description 1
- KXZLHMICGMACLR-UHFFFAOYSA-N 2-(hydroxymethyl)-2-pentylpropane-1,3-diol Chemical compound CCCCCC(CO)(CO)CO KXZLHMICGMACLR-UHFFFAOYSA-N 0.000 description 1
- COJADMTVMJHMNE-UHFFFAOYSA-N 6,6-diethyloctanoic acid Chemical compound CCC(CC)(CC)CCCCC(O)=O COJADMTVMJHMNE-UHFFFAOYSA-N 0.000 description 1
- IXSNSMTVBCIFOP-UHFFFAOYSA-N 6-(8-methylnonoxy)-6-oxohexanoic acid Chemical compound CC(C)CCCCCCCOC(=O)CCCCC(O)=O IXSNSMTVBCIFOP-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229940067597 azelate Drugs 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-M nonanoate Chemical compound CCCCCCCCC([O-])=O FBUKVWPVBMHYJY-UHFFFAOYSA-M 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
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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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
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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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- 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
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- 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
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- 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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- 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
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
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- 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
- C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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- 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
- C10M2209/11—Complex polyesters
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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
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/068—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings
-
- 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
- C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
-
- 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
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/28—Amides; Imides
-
- 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
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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
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- 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
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
-
- 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
- C10N2040/20—Metal working
- C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
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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
- C10N2040/20—Metal working
- C10N2040/241—Manufacturing joint-less pipes
-
- 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
- C10N2040/20—Metal working
- C10N2040/242—Hot working
-
- 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
- C10N2040/20—Metal working
- C10N2040/243—Cold working
-
- 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
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
-
- 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
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/245—Soft metals, e.g. aluminum
-
- 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
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/246—Iron or steel
-
- 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
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/247—Stainless steel
Definitions
- ABSTRACT Lubricating compositions particularly useful for manufacturing multigrade oils, hydraulic fluids, oils for industrial gears and cutting oils, comprising 95 percent by weight of a hydrocarbon oil produced according to a conventional process and 5-95 percent by weight of a compound selected from the group consisting of the esters of polyalkyleneglycol ethers complying with the general formula:
- R is a divalent hydrocarbon radical having from one to 34 carbon atoms
- R and R are divalent aliphatic radicals having from two to five carbon atoms
- R and R are monovalent hydrocarbon radicals having from one to twenty-five carbon atoms
- n and n are integers from two to 50, and those complying with the general formula:
- R is a hydrocarbon radical of valency m, having from three to carbon atoms, R is a monovalent hydrocarbon radical having from one to carbon atoms, R is a divalent aliphatic radical having from two to five carbon atoms, n is an integer from two to and m is an integer from two to four.
- This invention relates to new lubricating compositions consisting of mixtures of conventional hydrocarbon oils and derivatives of polyalkyleneglycols.
- the conventional base oils are prepared according to different methods.
- the main processes for manufacturing these oils are the acid or solvent refining of vacuum distillates or deasphalted vacuum residues from crude oils, the hydrotreatment of the same petroleum cuts and the oligomerization of olefinic hydrocarbons.
- a vacuum distillate or deasphalted vacuum residue can be subjected to a solvent extraction for example by means of furfurol or phenol, so as to eliminate from the petroleum cut the aromatic compounds contained therein, then to a series of treatments such as dewaxing, clay bleaching and moderate hydrogenation, at a temperature of from 250 to 350C, under a hydrogen pressure of 20 to 80 kg/cm in the presence of a catalyst.
- the second process the hydrotreatment of the abovementioned petroleum cuts, may be achieved, for example, according to the teaching of US. Pat. No. 3,560,370, in the name of the applicant.
- the hydrotreatment is conducted at a temperature of from 350 to 450C, under a hydrogen pressure of from 80 to 240 kg/cm and in the presence of a catalyst.
- the oil is manufactured by oligomerizing olefinic hydrocarbons having from two to 20 and preferably from nine to 16 carbon atoms per molecule.
- This oligomerization may be achieved by the action of catalysts consisting of aluminium halides, or by the action of heat, in the presence of organic peroxides acting as initiators.
- the oils prepared according to the above-described processes generally exhibit viscosity indexes of from 50 to 160 and, more particularly, from 50 to H for solvent refined oils, from 50 to 150 for the hydrorefined oils and from 1 l0 to 160 for the oligomerization oils.
- oils obtained in the two last above-described processes already exhibit much better characteristics than those obtained by the first process.
- all these oils require the addition, besides the conventional additives such as detergents or antioxidants, of more or less substantial amounts of viscosity additives, which however, exhibit inherent disadvantages such as poor thermal and/or mechanical stability.
- the present invention relates to new lubricating compositions which contain generally a compound (A) consisting of a hydrocarbon oil and a compound (B) selected amongst the esters of polyalkyleneglycol ethers.
- the hydrocarbon oil (A) is selected among the mineral oils obtained either by solvent refining or by acid treatment, or by severe hydrotreatment of vacuum distillates or deasphalted vacuum residues from crude oils and the synthetic oils obtained by oligomerizing olefinic hydrocarbons having from two to 20 carbon atoms per molecule.
- compound (B) results from the esterification of a dicarboxylic acid by at least one ether of polyalkyleneglycol and of monoalcohol or by the esterifi cation of an ether of polyalkyleneglycol and of polyol by at least one monocarboxylic acid.
- compound (B) complies with the general formula wherein R is a divalent hydrocarbon radical having from one to 34 carbon atoms, R and R are divalent aliphatic radicals having from two to five carbon atoms, R and R' are monovalent hydrocarbon radicals having from one to 25 carbon atoms, and n and n are integers from two to 50, or with the general formula wherein R is a hydrocarbon radical of valency m,
- catingcompositions exhibiting viscosity-temperature I characteristics so improved that the amount of viscoshaving from three to 15 carbon atoms, R; is a monovalent hydrocarbon radical having from one to 25 carbon atoms, R is a divalent aliphatic radical having from two to five carbon atoms, n is'an integer from two to 50 and m is an integer from two to four, with the provision that radicals R and R and integer n may be different from one chain to another.
- Compound (B) may also result from the esterification of an ether of polyalkyleneglycol and of polyol having the formula wherein R R n and m are defined as above, by means of a mixture of monocarboxyli'c acids and dicarboxylic acids HO-C-Rr-C-OH,
- esters of polyalkeneglycol ethers contemplated according to this invention are miscible with mineral or synthetic oils in rather large proportions, their miscibility with fluid oils being better than with more viscous oils, and better with naphthenic oils than with paraffinic oils.
- polyethyleneglycol derivatives for a given oil, are less easily miscible than those of polypropyleneglycol, there are used preferably polypropyleneglycol derivatives or still mixed derivatives of poly (ethylene-propylene)glycol in which the ratio ethylene oxide/propylene oxide is kept lower than or equal to l/l.
- compounds (B) that can be used in the compositions according to the invention, there can be mentioned the dodecanedioate of the ether obtained by condensation of propylene oxide with isobutanol;
- trioleate of the ether obtained by condensation of a mixture of ethylene and propylene oxides (50/50 by weight) with trimethylolhexane; the tetraheptanoate of the ether obtained by condensation of propylene oxide with pentaerythritol;
- compositions according to the invention may contain the hydrocarbon oil (A) in a major proportion (50 to 95 percent by weight) as compared withthe ester of polyalkyleneglycol ether (B) (5 to 50 percent by weight), or, on the contrary, the compound (B) may be present in a major proportion (50 to 95 percent by weight) as compared with the compound (A) (5 to 50 percent by weight). More generally, the compositions containing from 5 to percent by weight of each of the compounds (A) and (B) are to be considered.
- a third solvent such as an ester of dicarboxylic acid or of polyol, e.g., isodecyl adipate, trimethylhexyl azelate, neopentylglycol pelargonate, ethylhexyl sebacate, trimethylolpropane tripelargonate.
- a third solvent such as an ester of dicarboxylic acid or of polyol, e.g., isodecyl adipate, trimethylhexyl azelate, neopentylglycol pelargonate, ethylhexyl sebacate, trimethylolpropane tripelargonate.
- compositions of the invention may be used for manufacturing motor oils and particularly multigrade oils; they are also advantageously used for manufacturing hydraulic fluids, oils for gear-boxes, oils for industrial gears or oils for the cut or the forming of metals.
- the lubricating and anti-wear properties of the compositions according to the invention appear of particular interest since they permit a good working security and an extended life for the mechanisms lubricated therewith.
- esters of polyalkyleneglycol ethers used in the lubricating compositions of the invention may be prepared by direct esterification of the ether obtained by condensing at least one alkylene oxide with the suitable monoalcohol or polyol, by means of one or more convenient mono or dicarboxylic acids, in the presence of a convenient catalyst, the water produced being removable by azeotropic entrainement by means of a solvent.
- the remaining acidic products may be removed either by washing with a hydroalcoholic potash solution and then with water or by clay treatment.
- the solvent is then expelled under vacuum and the residue, consisting of the ester of polyalkyleneglycol ether, may be recovered without having to be distilled.
- Test of Lubricating Power A lubricating composition consisting of 50 percent by weight of l50'neutral mineral oil and 50 percent by weight of trioleate of the ether obtained by condensation of a 5050 mixture of ethylene oxide and propylene oxide with trimethylolpropane, has been tested for its anti-wear properties and its load capacity.
- the conditions of the anti-wear test are running speed 1,500 runs per minute,
- the average diameter of the three lower balls is an indication of the anti-wear power under limit lubrication conditions.
- R is a divalent aliphatic hydrocarbon radical
- a third solvent selected from the group consisting of: (a) esters of dicarboxylic acids and aliphatic monoalcohols, and (b) esters of monocarboxylic acids and aliphatic polyolst 4.
- compound (B) is selected from the group consisting of the esters resulting from the simultaneous esterification of an ether obtained by condensation of propylene oxide with trimethylol propane with a mixture, in a molar ratio of 4/1 of dodecanoic acid and azelaic acid, and the esters resulting from the simultaneous esterifi-
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7043605A FR2116277A1 (en) | 1970-12-03 | 1970-12-03 | Lube oil blends - contg hydrocarbon oil and polyalkylene glycol deriv |
| FR717113437A FR2133515B2 (enExample) | 1970-12-03 | 1971-04-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3773668A true US3773668A (en) | 1973-11-20 |
Family
ID=26216083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00204329A Expired - Lifetime US3773668A (en) | 1970-12-03 | 1971-12-02 | Lubricating compositions |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3773668A (enExample) |
| JP (1) | JPS5339441B1 (enExample) |
| BE (1) | BE775839A (enExample) |
| CA (1) | CA982542A (enExample) |
| DE (1) | DE2159511A1 (enExample) |
| ES (1) | ES397616A1 (enExample) |
| FR (1) | FR2133515B2 (enExample) |
| GB (1) | GB1372375A (enExample) |
| IT (1) | IT941944B (enExample) |
| NL (1) | NL7116645A (enExample) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036771A (en) * | 1975-04-16 | 1977-07-19 | Institut Francais Du Petrole | Lubricating bases for multigrade oils |
| US4339236A (en) * | 1978-02-21 | 1982-07-13 | Union Carbide Corporation | Low foam scouring agents |
| US4585565A (en) * | 1984-11-23 | 1986-04-29 | Aluminum Company Of America | Metalworking lubricant comprising mineral oil and alkoxyalkyl ester |
| US4618441A (en) * | 1984-11-23 | 1986-10-21 | Aluminum Company Of America | Metalworking with a lubricant composition comprising mineral oil and alkoxyalkyl ester |
| WO1988005809A1 (en) * | 1987-02-06 | 1988-08-11 | Gaf Corporation | Propoxylated guerbet alcohols and esters thereof |
| US4830769A (en) * | 1987-02-06 | 1989-05-16 | Gaf Corporation | Propoxylated guerbet alcohols and esters thereof |
| US4928190A (en) * | 1984-03-13 | 1990-05-22 | Olympus Optical Co., Ltd. | Magnetic recording/reproduction apparatus |
| US5045586A (en) * | 1988-08-04 | 1991-09-03 | Lenick Jr Anthony J O | Lubricants for thermoplastic resins |
| US5185092A (en) * | 1990-01-31 | 1993-02-09 | Tonen Corporation | Lubricating oil for refrigerator |
| US5820777A (en) * | 1993-03-10 | 1998-10-13 | Henkel Corporation | Blended polyol ester lubricants for refrigerant heat transfer fluids |
| US5851968A (en) * | 1994-05-23 | 1998-12-22 | Henkel Corporation | Increasing the electrical resistivity of ester lubricants, especially for use with hydrofluorocarbon refrigerants |
| US5906769A (en) * | 1992-06-03 | 1999-05-25 | Henkel Corporation | Polyol ester lubricants for refrigerating compressors operating at high temperatures |
| US5976399A (en) * | 1992-06-03 | 1999-11-02 | Henkel Corporation | Blended polyol ester lubricants for refrigerant heat transfer fluids |
| US6183662B1 (en) | 1992-06-03 | 2001-02-06 | Henkel Corporation | Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures |
| US6221272B1 (en) | 1992-06-03 | 2001-04-24 | Henkel Corporation | Polyol ester lubricants for hermetically sealed refrigerating compressors |
| US6544937B2 (en) * | 2001-05-22 | 2003-04-08 | Exxonmobile Research And Engineering Company | Demulsification of industrial lubricants containing naphthenic basestocks |
| US7018558B2 (en) | 1999-06-09 | 2006-03-28 | Cognis Corporation | Method of improving performance of refrigerant systems |
| US20110150163A1 (en) * | 2009-12-22 | 2011-06-23 | Westinghouse Electric Company Llc | Process for application of lubricant to fuel rod during fuel assembly loading process |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012158503A1 (en) * | 2011-05-13 | 2012-11-22 | Tenstech Inc. | Esters of structurally symmetric alkoxylated polyols and lubricating compositions comprising the same |
-
1971
- 1971-04-15 FR FR717113437A patent/FR2133515B2/fr not_active Expired
- 1971-11-25 CA CA128,603A patent/CA982542A/en not_active Expired
- 1971-11-26 BE BE775839A patent/BE775839A/xx not_active IP Right Cessation
- 1971-12-01 DE DE19712159511 patent/DE2159511A1/de active Pending
- 1971-12-02 GB GB5599371A patent/GB1372375A/en not_active Expired
- 1971-12-02 US US00204329A patent/US3773668A/en not_active Expired - Lifetime
- 1971-12-02 IT IT31930/71A patent/IT941944B/it active
- 1971-12-02 ES ES397616A patent/ES397616A1/es not_active Expired
- 1971-12-03 NL NL7116645A patent/NL7116645A/xx unknown
- 1971-12-03 JP JP9826271A patent/JPS5339441B1/ja active Pending
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036771A (en) * | 1975-04-16 | 1977-07-19 | Institut Francais Du Petrole | Lubricating bases for multigrade oils |
| US4339236A (en) * | 1978-02-21 | 1982-07-13 | Union Carbide Corporation | Low foam scouring agents |
| US4928190A (en) * | 1984-03-13 | 1990-05-22 | Olympus Optical Co., Ltd. | Magnetic recording/reproduction apparatus |
| US4585565A (en) * | 1984-11-23 | 1986-04-29 | Aluminum Company Of America | Metalworking lubricant comprising mineral oil and alkoxyalkyl ester |
| US4618441A (en) * | 1984-11-23 | 1986-10-21 | Aluminum Company Of America | Metalworking with a lubricant composition comprising mineral oil and alkoxyalkyl ester |
| WO1988005809A1 (en) * | 1987-02-06 | 1988-08-11 | Gaf Corporation | Propoxylated guerbet alcohols and esters thereof |
| US4830769A (en) * | 1987-02-06 | 1989-05-16 | Gaf Corporation | Propoxylated guerbet alcohols and esters thereof |
| US5045586A (en) * | 1988-08-04 | 1991-09-03 | Lenick Jr Anthony J O | Lubricants for thermoplastic resins |
| US5185092A (en) * | 1990-01-31 | 1993-02-09 | Tonen Corporation | Lubricating oil for refrigerator |
| US6296782B1 (en) | 1992-06-03 | 2001-10-02 | Henkel Corporation | Polyol ester lubricants for refrigerator compressors operating at high temperatures |
| US6666985B2 (en) | 1992-06-03 | 2003-12-23 | Cognis Corporation | Polyol ester lubricants for hermetically sealed refrigerating compressors |
| US5906769A (en) * | 1992-06-03 | 1999-05-25 | Henkel Corporation | Polyol ester lubricants for refrigerating compressors operating at high temperatures |
| US5976399A (en) * | 1992-06-03 | 1999-11-02 | Henkel Corporation | Blended polyol ester lubricants for refrigerant heat transfer fluids |
| US6183662B1 (en) | 1992-06-03 | 2001-02-06 | Henkel Corporation | Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures |
| US6221272B1 (en) | 1992-06-03 | 2001-04-24 | Henkel Corporation | Polyol ester lubricants for hermetically sealed refrigerating compressors |
| US6551524B2 (en) | 1992-06-03 | 2003-04-22 | Cognis Corporation | Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures |
| US5820777A (en) * | 1993-03-10 | 1998-10-13 | Henkel Corporation | Blended polyol ester lubricants for refrigerant heat transfer fluids |
| US5851968A (en) * | 1994-05-23 | 1998-12-22 | Henkel Corporation | Increasing the electrical resistivity of ester lubricants, especially for use with hydrofluorocarbon refrigerants |
| US6551523B1 (en) | 1995-06-07 | 2003-04-22 | Cognis Corporation | Blended polyol ester lubricants for refrigerant heat transfer fluids |
| US7018558B2 (en) | 1999-06-09 | 2006-03-28 | Cognis Corporation | Method of improving performance of refrigerant systems |
| US6544937B2 (en) * | 2001-05-22 | 2003-04-08 | Exxonmobile Research And Engineering Company | Demulsification of industrial lubricants containing naphthenic basestocks |
| US20110150163A1 (en) * | 2009-12-22 | 2011-06-23 | Westinghouse Electric Company Llc | Process for application of lubricant to fuel rod during fuel assembly loading process |
| US8599990B2 (en) * | 2009-12-22 | 2013-12-03 | Westinghouse Electric Company Llc | Process for application of lubricant to fuel rod during fuel assembly loading process |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2133515A2 (enExample) | 1972-12-01 |
| NL7116645A (enExample) | 1972-06-06 |
| IT941944B (it) | 1973-03-10 |
| FR2133515B2 (enExample) | 1974-07-05 |
| BE775839A (fr) | 1972-05-26 |
| ES397616A1 (es) | 1975-03-16 |
| GB1372375A (en) | 1974-10-30 |
| CA982542A (en) | 1976-01-27 |
| DE2159511A1 (de) | 1972-06-08 |
| JPS5339441B1 (enExample) | 1978-10-21 |
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