US3816312A - Lubricating compositions inhibited from oxidation - Google Patents
Lubricating compositions inhibited from oxidation Download PDFInfo
- Publication number
- US3816312A US3816312A US00289227A US28922772A US3816312A US 3816312 A US3816312 A US 3816312A US 00289227 A US00289227 A US 00289227A US 28922772 A US28922772 A US 28922772A US 3816312 A US3816312 A US 3816312A
- Authority
- US
- United States
- Prior art keywords
- thiophthene
- thio
- oxidation
- derivative
- per cent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000001050 lubricating effect Effects 0.000 title claims abstract description 22
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 230000003647 oxidation Effects 0.000 title abstract description 14
- 238000007254 oxidation reaction Methods 0.000 title abstract description 14
- JUEJPBZMWHMMPS-UHFFFAOYSA-N 1$l^{4},2,8-trithiabicyclo[3.3.0]octa-1(5),3,6-triene Chemical class S1C=CC2=S1SC=C2 JUEJPBZMWHMMPS-UHFFFAOYSA-N 0.000 claims abstract description 18
- SRYTYXMHFJHYIZ-UHFFFAOYSA-N 3,7-diphenyl-1$l^{4},2,8-trithiabicyclo[3.3.0]octa-1(5),3,6-triene Chemical group S1C(C=2C=CC=CC=2)=CC(C=2)=S1SC=2C1=CC=CC=C1 SRYTYXMHFJHYIZ-UHFFFAOYSA-N 0.000 claims description 2
- -1 methoxyphenyl thio-thiophthene Chemical compound 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 7
- 239000002480 mineral oil Substances 0.000 abstract description 4
- 235000010446 mineral oil Nutrition 0.000 abstract description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract description 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000004171 alkoxy aryl group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000654 additive Substances 0.000 description 10
- 230000003064 anti-oxidating effect Effects 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 238000006388 chemical passivation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002968 pentalenes Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/10—Compounds containing silicon
-
- 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
- C10M2203/06—Well-defined aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/106—Thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
-
- 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
Definitions
- said oxidation products deposit either as pitch products or varnish, or as lacquers on said metal surfaces thus causing a decrease of the efficiency of the engine itself.
- antioxidizer additives such as the sterically hindered phenols, aromatic amines, alkylphenols sulphides, dialkylphosphates of Ca, Ba, and Al and other numerous ones.
- additives which are inhibitors of oxidation for a wide range of products, such as lubricating compositions containing mineral oils, obtained from the most different raw materials refined through acids or solvents or coming from hydrocracking, said additives being also suitable to inhibit from oxidation lubricating compositions containing synthetic bases, such as synthetic hydrocarbons, synthetic esters, silicones, hydrogenated polyolefins, polyalkylen oxides, alkybenzenes, esters of phosphoric acid, and others.
- synthetic bases such as synthetic hydrocarbons, synthetic esters, silicones, hydrogenated polyolefins, polyalkylen oxides, alkybenzenes, esters of phosphoric acid, and others.
- the thio-thiophthene derivatives may be represented by the following general formula rectly or by an equal GHQ-CH3 group to the other alkylene radical.
- Said antioxidizing additives dissolve in the lubricating fluid by heating to a temperature not higher than 70-80 C.
- the amount of the derivatives of the thiothiophthene which are used depends or various factors such as the nature of the base and the presence of others additives.
- thiothiophthenes are used in concentrations which range from the 0.001 percent to 10 percent by weight and preferably from the 0.01 to the 5 percent b.w.
- the lubricants containing the antioxidizers of the invention may also contain various other types of addit'ives normally used, like detergents, dispersants corrosion inhibitors and antirust, viscosity index improvers, sludge inhibitors, pour point depressants and also other antioxidizers in the case it were desirable to improve the characteristics of the oxidation inhibition of compositions already containing antioxidizing agents.
- the method of preparation consists in causing the triketones, dissolved generally in aromatic solvents, to react with P 8
- the reaction mass is treated with aqueous NaOl-l and the desired product crystallizes out of the organic phase.
- inventive antioxidizers may also be named as derivatives of thio-thiophthene, and they may also be named as trithio-l,5,6 S pentalenes.
- Boiling was maintained during about 2 hours.
- the residue was subjected to two further extractions with benzene.
- the benzene extracts were gathered, washed with H 0 and concentrated by evaporating the benzene.
- EXAMPLE 2 With the purpose of evaluating the antioxidizing properties of the thio-thiophthene derivatives in lubricating compositions, some tests of oxygen absorption were carried out. Said test was efiected in an apparatus of the type described by G. Miliotis and co-operators (Bull. Soc. Chim. France, 1969; 847) and consisted in determining the induction period of the oxidation of a product maintained under a strong stirring in a reactor provided with a thermostat. The reactor filled with oxygen, was connected with a graduated buret for gases, which was also filled with oxygen.
- the tests were carried out at l60i2C on 10 ml. oil oils, at temperatures not higher than 80 C and in a samples, by using as catalyst copper powder in an quantity ranging from 0.001 to 10 per cent by weight, amount of 50 mg. a derivative of thio-thiophthene represented by the The inventive products were dissolved in paraffinic 5 general formula: mineral oil having a 30 SAE viscosity grade.
- R 5 2 R1 Induction l0 4 3 Number of Concentration period/ R2 R3 the test Additive moles/liter minutes v 1 none 14 wherein R, R R and R which may be the same or 2 y y -2 270 different, are members of the group consisting of hy- 3 2126thytinmemoxwhewt -2 638 15 drogen, alkyl, cycloalkyl, aryl, alkylaryl, arylalkyl, al-
- thio-thiophthene koxyaryl, alkoxyalkyl and aroxyalkyl, or R and R 4 10-2 662 represent a CH Cit-CH or Cl-l -CH -CH alkylene phenyl-thio-thiophthene radical connecting the number 3 and 4 carbon atoms of the thio-thiophthene molecule.
- EXAMPLE 3 ,2O Lubricating composition according to claim 1 Through the apparatus and the method described in characterized in that the derivative of the thio-' example 2 the additives of the invention dissolved in thiophthene is 2-methyl-5. methoxyphenyl thiotrimethyl adipate of octyl gave the results reported in thiophthene and is present in an amount in the range I table 2. H of 0.01 to 5 per cent by weight.
- the derivatives of thio-thiophthene may be advanta- 4O 3.
- Lubricating composition according to claim 1 geously used in oils for engines and for gears, in various characterized in that the derivative of the thiohydraulic fluids and generally transmission fluids, in inthiophthene is 2,5 di p. methoxyphenyl-3-phenyl thiodustrial and marine oils. thiophthene and is present in an amount in the range From tables 1 and 2 it is possible to notice that the of 0.01 to 5 per cent by weight.
- Lubl'lcatlng composition according to Claim 1 well known commercial antioxidizers such as 2,6 Characterized in at the derivative of the thiodi-t butyl-4-methyl phenol and phenyl-a- IhlOPhfl'lCnB 15 2,5 dlPhCIIYI-IhlO-thlOPhthGl'lfi and i5 h h 1 i present in an amount in the range of 0.01 to 5 per cent
- Said derivatives of thio-thiophthene as already rey ported particularly prevent the oxidation of various 5O f lg composition according to Claim 1 types of lubricating bases at high temperatures and characterlzeq that the erivative of the thioachieve the purposes of the invention both as above thiophthene 15 5 di P- yp y 'l mentioned from the point of view of a better activity as two-thiophthene and i5 Present in an
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2871171 | 1971-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3816312A true US3816312A (en) | 1974-06-11 |
Family
ID=11224043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00289227A Expired - Lifetime US3816312A (en) | 1971-09-16 | 1972-09-15 | Lubricating compositions inhibited from oxidation |
Country Status (18)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4777307A (en) * | 1987-12-14 | 1988-10-11 | Exxon Research And Engineering Company | Method for improving the oxidation stability of refined hydrocarbon oils |
| US4822506A (en) * | 1986-11-12 | 1989-04-18 | Ciba-Geigy Corporation | Lubricant additives containing sulfur |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5214587A (en) * | 1975-07-25 | 1977-02-03 | Citizen Watch Co Ltd | Continuous delivery mechanism of the device for foring vacuum coatings |
| JPS54123616U (enrdf_load_stackoverflow) * | 1978-02-17 | 1979-08-29 | ||
| JPS5980466U (ja) * | 1982-11-20 | 1984-05-31 | ティーディーケイ株式会社 | 蒸着装置 |
-
0
- BE BE788424D patent/BE788424A/xx unknown
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1972
- 1972-08-16 AU AU45640/72A patent/AU471053B2/en not_active Expired
- 1972-08-30 DE DE2242637A patent/DE2242637C3/de not_active Expired
- 1972-09-01 NL NL7211982.A patent/NL161810C/xx not_active IP Right Cessation
- 1972-09-05 FR FR7231344A patent/FR2154460B1/fr not_active Expired
- 1972-09-09 CH CH1321772A patent/CH559769A5/xx not_active IP Right Cessation
- 1972-09-11 GB GB4216972A patent/GB1385950A/en not_active Expired
- 1972-09-13 LU LU66066A patent/LU66066A1/xx unknown
- 1972-09-13 CA CA151,661A patent/CA1001148A/en not_active Expired
- 1972-09-14 ES ES406882A patent/ES406882A1/es not_active Expired
- 1972-09-14 PL PL1972157755A patent/PL71128B1/pl unknown
- 1972-09-15 DK DK456472A patent/DK144216C/da not_active IP Right Cessation
- 1972-09-15 DD DD165696A patent/DD103013A5/xx unknown
- 1972-09-15 CS CS726330A patent/CS174838B2/cs unknown
- 1972-09-15 US US00289227A patent/US3816312A/en not_active Expired - Lifetime
- 1972-09-15 AT AT793772A patent/AT320832B/de not_active IP Right Cessation
- 1972-09-15 HU HU72SA00002401A patent/HU171954B/hu unknown
- 1972-09-16 JP JP47092256A patent/JPS5233122B2/ja not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4822506A (en) * | 1986-11-12 | 1989-04-18 | Ciba-Geigy Corporation | Lubricant additives containing sulfur |
| US4777307A (en) * | 1987-12-14 | 1988-10-11 | Exxon Research And Engineering Company | Method for improving the oxidation stability of refined hydrocarbon oils |
Also Published As
| Publication number | Publication date |
|---|---|
| AU471053B2 (en) | 1976-04-08 |
| GB1385950A (en) | 1975-03-05 |
| PL71128B1 (enrdf_load_stackoverflow) | 1974-04-30 |
| ES406882A1 (es) | 1975-10-01 |
| DD103013A5 (enrdf_load_stackoverflow) | 1974-01-05 |
| AU4564072A (en) | 1974-02-21 |
| NL161810C (nl) | 1980-03-17 |
| AT320832B (de) | 1975-02-25 |
| CS174838B2 (en) | 1977-04-29 |
| FR2154460A1 (enrdf_load_stackoverflow) | 1973-05-11 |
| LU66066A1 (enrdf_load_stackoverflow) | 1973-04-13 |
| DE2242637C3 (de) | 1975-08-21 |
| HU171954B (hu) | 1978-04-28 |
| FR2154460B1 (enrdf_load_stackoverflow) | 1974-08-30 |
| NL161810B (nl) | 1979-10-15 |
| DE2242637A1 (de) | 1973-03-29 |
| DE2242637B2 (de) | 1975-01-16 |
| NL7211982A (enrdf_load_stackoverflow) | 1973-03-20 |
| JPS5233122B2 (enrdf_load_stackoverflow) | 1977-08-26 |
| DK144216B (da) | 1982-01-18 |
| SU442604A3 (ru) | 1974-09-05 |
| DK144216C (da) | 1982-06-14 |
| JPS4838306A (enrdf_load_stackoverflow) | 1973-06-06 |
| BE788424A (fr) | 1973-01-02 |
| CH559769A5 (enrdf_load_stackoverflow) | 1975-03-14 |
| CA1001148A (en) | 1976-12-07 |
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