EP0328642B1 - Traction fluid - Google Patents
Traction fluid Download PDFInfo
- Publication number
- EP0328642B1 EP0328642B1 EP87904959A EP87904959A EP0328642B1 EP 0328642 B1 EP0328642 B1 EP 0328642B1 EP 87904959 A EP87904959 A EP 87904959A EP 87904959 A EP87904959 A EP 87904959A EP 0328642 B1 EP0328642 B1 EP 0328642B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- traction
- traction fluid
- fluid
- olefin
- carbon atoms
- 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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- 239000012530 fluid Substances 0.000 title claims abstract description 60
- 229920013639 polyalphaolefin Polymers 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 150000005690 diesters Chemical class 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 150000002148 esters Chemical group 0.000 claims description 7
- 229920001083 polybutene Polymers 0.000 claims description 7
- 239000002199 base oil Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000005540 biological transmission Effects 0.000 abstract description 14
- 238000013329 compounding Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- -1 alkane compound Chemical class 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 229920002367 Polyisobutene Polymers 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 239000004711 α-olefin Substances 0.000 description 4
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000005096 rolling process Methods 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- QRRSHRVKVLSFQS-UHFFFAOYSA-N 1-ethylcyclohexane-1-carboxylic acid Chemical compound CCC1(C(O)=O)CCCCC1 QRRSHRVKVLSFQS-UHFFFAOYSA-N 0.000 description 1
- REHQLKUNRPCYEW-UHFFFAOYSA-N 1-methylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1(C)CCCCC1 REHQLKUNRPCYEW-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VOWAEIGWURALJQ-UHFFFAOYSA-N Dicyclohexyl phthalate Chemical compound C=1C=CC=C(C(=O)OC2CCCCC2)C=1C(=O)OC1CCCCC1 VOWAEIGWURALJQ-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- IOUOYKTVGQHNMO-UHFFFAOYSA-N dicyclohexyl cyclohexane-1,1-dicarboxylate Chemical compound C1CCCCC1(C(=O)OC1CCCCC1)C(=O)OC1CCCCC1 IOUOYKTVGQHNMO-UHFFFAOYSA-N 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
- C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
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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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/34—Esters of 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/36—Esters of polycarboxylic 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
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- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
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- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
- C10M107/06—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing propene
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- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
- C10M107/08—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing butene
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- C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
- C10M143/04—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing propene
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- C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
- C10M143/06—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing butene
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- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
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- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/002—Traction fluids
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- 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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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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- C10M2205/0206—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers used as base material
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- 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
- C10M2205/024—Propene
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- 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
- C10M2205/024—Propene
- C10M2205/0245—Propene used as base material
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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- C10M2205/026—Butene
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- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
- C10M2205/0265—Butene used as base material
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- 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
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
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- 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
- C10M2207/2815—Esters of (cyclo)aliphatic monocarboxylic acids used as base material
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- 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
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- 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
- C10M2207/2825—Esters of (cyclo)aliphatic oolycarboxylic acids used as base material
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- 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
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
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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
- C10M2207/284—Esters of aromatic monocarboxylic acids
- C10M2207/2845—Esters of aromatic monocarboxylic acids used as base material
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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
- C10M2207/285—Esters of aromatic polycarboxylic acids
- C10M2207/2855—Esters of aromatic polycarboxylic acids used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
- C10M2213/023—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only used as base material
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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
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
- C10M2213/043—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen used as base material
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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
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/06—Perfluoro polymers
- C10M2213/0606—Perfluoro polymers used as base material
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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
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/06—Perfluoro polymers
- C10M2213/062—Polytetrafluoroethylene [PTFE]
- C10M2213/0623—Polytetrafluoroethylene [PTFE] used as base material
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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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
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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
- 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
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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
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for 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
- C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
Definitions
- This invention relates to a traction fluid. More particularly, the present invention is concerned with a traction fluid comprising a diester or its derivative having two cyclohexyl rings, and a branched poly- ⁇ -olefin as the base oil.
- Traction drive power transmissions which transmit power to a driven part through a traction drive mechanism, have attracted attention in the field of automobiles and industrial machinery, and in recent years research and development thereon has progressed.
- the traction drive mechanism is a power transmitting mechanism using a rolling friction. Unlike conventional drive mechanisms it does not use any gears, which enables a reduction in vibration and noise as well as a smooth speed change in high-speed rotation.
- An important goal in the automobile industry is improvement in the fuel economy of automobiles. It has been suggested that if the traction drive is applied to the transmission of automobiles to convert the transmission to a continuous variable-speed transmission the fuel consumption can be reduced by 20% or more compared to conventional transmission systems since the drive can always be in the optimum speed ratio.
- traction coefficient is defined as the ratio of the tractional force which is caused by slipping at the contact points between rotators which are in contact with each other in a power transmission of the rolling friction type to the normal load.
- the traction fluid is required to be comprised of a lubricating oil having a high traction coefficient. It has been confirmed that a traction fluid possessing a molecular structure having a naphthene ring exhibits a high performance. "Santotrack ®" manufactured by the Monsanto Chemical Company is widely known as a commercially available traction fluid. Japanese Patent Publication No. 35763/1972 discloses di(cyclohexyl)alkane and dicyclohexane as traction fluids having a naphthene ring.
- the present inventors have made extensive and intensive studies with a view to developing a traction fluid which not only exhibits a high traction coefficient but which also is low in cost. As a result, they have found that the incorporation of a specified amount of branched poly- ⁇ -olefin into a diester or its derivative in which two cyclohexyl rings are connected through a linear chain hydrocarbon can provide an economical, high-performance base oil fluid, and achieved the present invention.
- the present invention relates to a traction fluid characterized by being a blend of a diester or its derivative represented by the following general formula wherein A′ is an ester linkage of -COO- or -OOC-, n is an integer of 1 to 10, R1 is independently selected from a hydrogen atom and alkyl groups having 1 to 8 carbon atoms, and R2 is independently selected from a hydrogen atom and alkyl groups having 1 to 3 carbon atoms: with 0.1 to 95% by weight of a branched poly- ⁇ -olefin.
- the first object of the present invention is to provide a high-performance traction fluid having a high traction coefficient.
- the second object of the present invention is to provide a traction fluid which is not only economical but also readily available and easily applicable to transmissions.
- the traction fluid of the present invention comprises a base oil comprised of two components, i.e., component A comprised of a diester or its derivative, and a specific amount of a component B comprised of a branched poly- ⁇ -olefin.
- component A is a diester or its derivative having two cyclohexyl rings and is represented by the above-mentioned structural formula.
- A′ of the ester linkage is -COO- or -OOC-, and the number.
- n. of the carbon atoms in the hydrocarbon skeleton is 1 to 10, preferably 1 to 4. When n is zero, the traction coefficient is low while when n is 11 or more the viscosity is unfavorably high.
- This diester or derivative thereof can be prepared by the methods stated below and has a viscosity of 5 to 50 mm2/s (cst,) preferably 7 to 30 mm2/s (cst) at 40°C, and 1 to 10 mm2/s (cst,) preferably 2 to 6 mm2/s (cst,) at 100°C.
- the derivative includes an amino compound, an ether compound, etc.
- the component A can be prepared by any of the following methods.
- the first method comprises an esterification reaction of a dihydric alcohol with a cyclohexanecarboxylic acid compound.
- the dihydric alcohol is selected from the group consisting of those having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms.
- examples of the dihydric alcohol include ethylene glycol. 1,3-propanediol, 1,3-butanediol and 1,4-butanediol.
- cyclohexanecarboxylic acid compound examples include, besides cyclohexanecarboxylic acid, those having an alkyl group with 1 to 8 carbon atoms, e.g., methylcyclohexanecarboxylic acid, ethylcyclohexanecarboxylic acid, etc. Cyclohexanecarboxylic acid is particularly preferred.
- the esterification reaction is conducted with an alcohol/acid molar ratio of 1:2, or in the presence of an excess amount of the acid.
- the former method requires the use of a catalyst and has the additional disadvantage that a monoalcohol is produced as the by-product. Therefore, it is preferred that the esterification reaction be conducted in the presence of an excess amount of the acid.
- reaction temperature is about 150 to 250°C, preferably 170 to 230°C, and the reaction time is 10 to 40 hr, preferably 15 to 25 hr.
- the esterification reaction may be conducted under either elevated or reduced pressures, it is preferred that the reaction is conducted at atmospheric pressure from the standpoint of ease of reaction operation. Under this condition the excess acid serves as a catalyst.
- An alkylbenzene such as xylene or toluene can be added in a suitable amount as a solvent. The addition of the solvent enables the reaction and temperature to be easily controlled.
- the reaction proceeds the water which forms during the reaction evaporates.
- the reaction is terminated when the amount of the water reaches, on a mole basis, twice that of the alcohol.
- the excess acid is neutralized with an aqueous alkaline solution and removed by washing with water.
- the reaction is conducted using the acid in an amount of 2 to 2.5-fold mol excess over the alcohol in the presence of a catalyst.
- the catalyst include phosphoric acid, p-toluenesulfonic acid, and sulfuric acid.
- the most preferable catalyst is phosphoric acid because it enhances the reaction rate and increases the yield of the ester.
- the reaction product is finally distilled under reduced pressure to remove water and the solvent thereby obtaining the diester compound of the present invention.
- the second method of producing the component A of the present invention comprises esterification of a cyclohexanol compound with a dicarboxylic acid having 3 to 12 carbon atoms.
- the cyclohexanol compound include, besides cyclohexanol, those having an alkyl group with 1 to 8 carbon atoms, e.g., methylcyclohexanol and tertbutylcyclohexanol. Cyclohexanol is particularly preferred.
- the dicarboxylic acid includes one having 3 to 12 carbon atoms in its main chain, preferably one having 3 to 6 carbon atoms in its main chain. Examples of the dicarboxylic acid include malonic acid, succinic acid and glutaric acid.
- the esterification reaction is conducted in an alcohol/acid molar ratio of 2:1 or in the presence of an excess amount of the alcohol.
- the esterification reaction is conducted in the presence of an excess amount of the alcohol.
- 1 mol of the dicarboxylic acid is reacted with the alcohol in 2.5 to 5-fold mol excess.
- the reaction temperature is about 150 to 250°C, preferably 170 to 230°C, and the reaction time is 10 to 40 hr, preferably 15 to 25 hr.
- the esterification reaction may be conducted under either elevated or reduced pressures, it is preferred that the reaction be conducted at atmospheric pressure from the standpoint of ease of reaction operation.
- An alkylbenzene such as xylene or toluene can be added in a suitable amount as a solvent.
- the addition of the solvent enables the reaction temperature to be easily controlled.
- the water which has been formed during the reaction evaporates.
- the reaction is terminated when the amount of the water reaches twice by mol that of the alcohol.
- Phosphoric acid, p-toluenesulfonic acid or sulfuric acid can be used as a catalyst.
- the most preferable catalyst is phosphoric acid because it enhances the reaction rate and increases the yield of the ester.
- the reaction product is finally distilled under reduced pressure to remove the water, solvent and excess alcohol thereby obtaining the diester compound of the present invention.
- the poly- ⁇ -olefin component B has either a quaternary carbon atom or a tertiary carbon atom in its main chain and is a polymer of an ⁇ -olefin having 3 to 5 carbon atoms or the hydrogenation product thereof.
- Examples of the poly- ⁇ -olefin include polypropylene, polybutene, polyisobutylene and polypentene and the hydrogenation products thereof. Polybutene, polyisobutylene and hydrogenation products thereof are particularly preferred.
- the polyisobutylene is represented by the following structural formula:
- the hydrogenation product of the polyisobutylene is represented by the following structural formula:
- the degree of polymerization, n is 6 to 200.
- polybutene and polyisobutylene used may be commercially available ones, they may also be produced by conventional and well known polymerization methods.
- the hydrogenation product thereof is produced by reacting polyisobutylene or the like in the presence of hydrogen.
- the molecular weight of the poly- ⁇ -olefin is preferably in the range of 500 to 10,000, more preferably in the range of 900 to 5,000.
- the molecular weight can be adjusted by suitable methods such as decomposition of a poly- ⁇ -olefin having a high molecular weight and mixing of poly- ⁇ -olefins having different molecular weights.
- OCP ⁇ -olefin copolymer
- the component A in the present invention e.g., a diester of succinic acid with cyclohexanol, exhibits a traction coefficient of 0.102 to 0.106, while the component B, e.g., polybutene, exhibits a traction coefficient of 0.075 to 0.085.
- a further improved traction fluid can be obtained by blending the component A with 0.1 to 95% by weight, particularly 10 to 70% by weight, of the poly- ⁇ -olefin of the component B.
- the gem-dialkyl group in the component B cooperates with the cyclohexyl ring in the component A to exhibit a synergistic effect (with respect to improvement in the traction coefficient).
- the component B is inexpensive and exhibits excellent viscosity characteristics, a traction fluid can be economically obtained by blending component A with 0.1 to 95% by weight of component B without lowering the traction coefficient.
- Various additives may also be added to the traction fluid of the present invention depending upon their applications. Specifically, when the traction device undergoes a high temperature and a large load at least one additive selected from among an antioxidant, a wear inhibitor and a corrosion inhibitor may be added in an amount of 0.01 to 5% by weight. Similarly, when a high viscosity index is required a known viscosity index improver is suitably added in an amount of 1 to 10% by weight. However, since the use of polymethacrylates or olefin copolymers lowers the traction coefficient, it is preferred that, if present, they are used in an amount of 4% or less by weight.
- traction fluid as used in the present invention is intended to mean a fluid for use in devices which transmit a rotational torque through point contact or line contact, or for use in transmissions having a similar structure.
- the traction fluid of the present invention exhibits a traction coefficient higher than those of conventionally known fluids, i.e., exhibits a traction coefficient 5 to 15% higher than those of the conventional fluids, although the value varies depending on the viscosity. Therefore, the traction fluid of the present invention can be advantageously used for relatively low power drive transmissions including internal combustion engines of small passenger cars, spinning machines and food producing machines, as well as large power drive transmissions such as industrial machines, etc.
- the traction fluid of the present invention is remarkably superior in its traction coefficient relative to conventional fluids.
- the reason why the traction fluid of the present invention exhibits a high traction coefficient is not yet fully understood. However, basically, the reason is believed to reside in the unique molecular structure of the traction fluid of the present invention.
- the component A of the traction fluid of the present invention comprises a diester having two cyclohexyl rings in its molecule.
- the two ester linkages bring about an interdipolar force between the molecules. It is believed that the interdipolar force serves to bring the fluid into a stable glassy state under high load conditions, thereby increasing the shear strength.
- the component B in the traction fluid of the present invention has a quaternary carbon atom of the gem-dialkyl type. Therefore when the traction device is under high load conditions the cyclohexyl rings are firmly engaged, like gears, with the gem-dialkyl portions of the quaternary carbon of the component B, while when the device is released from the load this engagement is quickly broken thereby causing fluidization.
- Diester A of the present invention was synthesized by the following method.
- cyclohexanol and 104 g of malonic acid i.e., 0.4 mol per mol of cyclohexanol
- phosphoric acid was added in an amount of 1% by weight based on the total weight of the reactants.
- the reactor was heated at 180°C.
- the contents of the reactor were allowed to react at a temperature in the range of 180°C to 210°C under atomospheric pressure.
- the reaction was stopped at a point when the water generated during the reaction amounted to twice, by mol. of the amount of the malonic acid.
- reaction mixture was washed with an alkaline solution to remove unreacted compounds from the mixture of the reaction products, i.e., a diester of cyclohexanol with malonic acid, the unreacted cyclohexanol and phosphoric acid, followed by vacuum distillation, thereby isolating a pure diester (A1).
- an alkaline solution to remove unreacted compounds from the mixture of the reaction products, i.e., a diester of cyclohexanol with malonic acid, the unreacted cyclohexanol and phosphoric acid, followed by vacuum distillation, thereby isolating a pure diester (A1).
- diesters A2 and A3 of the present invention were synthesized using the following raw materials:
- the diesters thus produced were each blended with polybutene having an average molecular weight of 900 to 2350 followed by the measurement of traction coefficient.
- the conditions of the measurement of the traction coefficient were as follows:
- the traction fluids of the present invention were found to be remarkably superior in traction performance to the conventional fluids as shown in Table 1.
- traction coefficients of the following traction fluids were measured under the same conditions as those used in the above examples: a traction fluid consisting of 100% by weight of the component B; traction fluids obtained by blending the component A1 to A3 with 5 to 30% by weight of OCP or PMA; and a commercially available traction fluid (Santotrack ®).
- OCP is an olefin copolymer. Specifically, an ethylene-propylene copolymer having an average molecular weight of 150,000 to 300,000 was used as OCP.
- PMA is a polymethyacrylate. Specifically, a polymer having an average molecular weight of 50,000 to 300,000 was used as PMA.
- the present invention relates to a traction fluid which comprises a component A comprised of a diester or the like having two cyclohexyl rings and linear-chain hydrocarbons as the skeleton and a specific amount of a component B comprised of a branched poly- ⁇ -olefin, and which exhibits not only an extremely high traction coefficient, but also is inexpensive and exhibits excellent viscosity characteristics.
- this traction fluid in a power transmission device, particularly a traction drive device, leads to a remarkable increase in shearing force under a high load, and at the same time enables reduction in size of the device and reduced cost of the device.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/JP1987/000565 WO1989001021A1 (fr) | 1987-07-30 | 1987-07-30 | Fluide de traction |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0328642A4 EP0328642A4 (en) | 1989-07-25 |
| EP0328642A1 EP0328642A1 (en) | 1989-08-23 |
| EP0328642B1 true EP0328642B1 (en) | 1993-03-10 |
Family
ID=13902781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP87904959A Expired - Lifetime EP0328642B1 (en) | 1987-07-30 | 1987-07-30 | Traction fluid |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0328642B1 (enExample) |
| JP (1) | JPS62177099A (enExample) |
| DE (1) | DE3784732D1 (enExample) |
| WO (1) | WO1989001021A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8626510D0 (en) * | 1986-11-06 | 1986-12-10 | Shell Int Research | Ester compounds as lubricants |
| JPS62177099A (ja) * | 1987-07-30 | 1987-08-03 | Toa Nenryo Kogyo Kk | トラクシヨン用フル−ド |
| JPH0747752B2 (ja) * | 1989-09-16 | 1995-05-24 | 株式会社コスモ総合研究所 | トラクションドライブ用流体 |
| US6372696B1 (en) | 1999-11-09 | 2002-04-16 | The Lubrizol Corporation | Traction fluid formulation |
| US7045488B2 (en) | 2002-05-16 | 2006-05-16 | The Lubrizol Corporation | Cylic oligomer traction fluid |
| JP4521275B2 (ja) * | 2002-09-18 | 2010-08-11 | 出光興産株式会社 | トラクションドライブ用流体組成物 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53127970A (en) * | 1977-04-14 | 1978-11-08 | Nippon Oil & Fats Co Ltd | Synthetic lubricating oil compound |
| JPS5496667A (en) * | 1977-12-29 | 1979-07-31 | Bayer Ag | Ester carboxylate of pentaerythritol |
| JPS5968397A (ja) * | 1982-10-13 | 1984-04-18 | Cosmo Co Ltd | リヤアクスル用ギヤ油組成物 |
| JPS59191797A (ja) * | 1983-04-14 | 1984-10-30 | Nippon Petrochem Co Ltd | トラクシヨンドライブ用流体 |
| JPS6119697A (ja) * | 1984-07-06 | 1986-01-28 | Nippon Steel Chem Co Ltd | トラクシヨンオイル組成物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3440894A (en) * | 1966-10-13 | 1969-04-29 | Monsanto Co | Tractants and method of use |
| DE2117323C3 (de) * | 1971-04-08 | 1978-08-31 | Robert Bosch Gmbh, 7000 Stuttgart | Temperaturschalter |
| JPS619497A (ja) * | 1984-06-25 | 1986-01-17 | Nippon Oil Co Ltd | 自動変速機油組成物 |
| JPS62177099A (ja) * | 1987-07-30 | 1987-08-03 | Toa Nenryo Kogyo Kk | トラクシヨン用フル−ド |
-
1986
- 1986-01-31 JP JP61019227A patent/JPS62177099A/ja active Granted
-
1987
- 1987-07-30 WO PCT/JP1987/000565 patent/WO1989001021A1/ja not_active Ceased
- 1987-07-30 EP EP87904959A patent/EP0328642B1/en not_active Expired - Lifetime
- 1987-07-30 DE DE8787904959T patent/DE3784732D1/de not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53127970A (en) * | 1977-04-14 | 1978-11-08 | Nippon Oil & Fats Co Ltd | Synthetic lubricating oil compound |
| JPS5496667A (en) * | 1977-12-29 | 1979-07-31 | Bayer Ag | Ester carboxylate of pentaerythritol |
| JPS5968397A (ja) * | 1982-10-13 | 1984-04-18 | Cosmo Co Ltd | リヤアクスル用ギヤ油組成物 |
| JPS59191797A (ja) * | 1983-04-14 | 1984-10-30 | Nippon Petrochem Co Ltd | トラクシヨンドライブ用流体 |
| JPS6119697A (ja) * | 1984-07-06 | 1986-01-28 | Nippon Steel Chem Co Ltd | トラクシヨンオイル組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0328642A1 (en) | 1989-08-23 |
| JPH0588760B2 (enExample) | 1993-12-24 |
| DE3784732T2 (enExample) | 1993-06-17 |
| EP0328642A4 (en) | 1989-07-25 |
| DE3784732D1 (de) | 1993-04-15 |
| WO1989001021A1 (fr) | 1989-02-09 |
| JPS62177099A (ja) | 1987-08-03 |
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