Classifications

• • 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
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
  • C08K5/45—Heterocyclic compounds having sulfur in the ring
  • C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
• • 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
  • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/26—Amines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • 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
  • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
• • 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
  • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the 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
  • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
  • C10M2225/041—Hydrocarbon polymers
• • 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
  • C10N2040/25—Internal-combustion engines
  • C10N2040/255—Gasoline engines
  • C10N2040/26—Two-strokes or two-cycle engines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2070/00—Specific manufacturing methods for lubricant compositions
  • C10N2070/02—Concentrating of additives

Definitions

• such phosphosulfurized hydrocarbons are prepared by reaction of a 150-50,000 fi polymer of low molecular weight monoolefin; e.g. propene, isobutylene or mixtures of isobutylene with butene-l and butene-Z, with a phosphorus sulfide, preferably P 8 in an amount from 5 to 25 percent by weight of the polymer at a temperature in the range of 93 to 232 C.
• a 150-50,000 fi polymer of low molecular weight monoolefin e.g. propene, isobutylene or mixtures of isobutylene with butene-l and butene-Z
• the resulting combination of such phosphosulfurized hydrocarbon polymer and minor amount, generally in the range of 0.1 to 50 weight percent of 2,5- bis(alkyldithio)-1,3,4-thiadiazole can be used as an addition agent for oleaginous based lubricants to lubricate internal combustion gasoline and diesel engines of 4 and 2 stroke cycles employing crankcase lubrication or lubrication by addition of lubricants to the engines fuel as is common in 2 stroke gasoline engines.
• Such use of the combination of such phosphosulfurized hydrocarbon polymer and minor amount of the bis(alkyldithio)thiadiazole provides an ashless-type inhibitor for bearing metal, especially Pb, Cu and Pb-Cu bearings, corrosion and for oxidative thickening of oleaginous base lubricants.
• the 2,5-bis(alkyldithio)-l,3,4-thiadiazoles and their preparation have been known from the teachings, respectively, in US. Pats. No. 2,719,126 and No. 3,087,932.
• Said bis(alkyldithio)thiadiazoles can have alkyl-substitucuts of from 1-280 carbon atoms and can be prepared by oxidative coupling of 2,5-dimercapto-1,3,4-thiadiazole with a C to C alkylhydrocarbon mercaptan in the respective reactant molar ratio of 1:2.
• the concentration of the preferred bis(alkyldithio)thiadiazole is 1 to 25 weight percent of the phosphosulfurized hydrocarbon polymer and such preference is based on the need for practical inhibition of bearing metal corrosion and oxidative thickening of the oleaginous base lubricant.
• the foregoing combination of phosphosulfurized hydrocarbon and l-25 weight percent thereof of the preferred 2,5-bis(alkyldithi0)-1,3,4-thiadiazole can be used as addition agent in oleaginous lubricants in concentrations of from 0.01 to 20 percent by volume (the combination is fluid) but preferably in concentrations of 0.1 to 10 volume percent based on practical needs for inhibiting bearing metal corrosion and oxidative thickening of oleaginous base lubricants.
• compositions of phosphosulfurized' hydrocarbon polymer and 1-25 weight percent bis- (alkyldithio)thiadiazole are useful in transmission and industrial lubricants where oxidative stability of the lubricants where oxidative stability of the lubricant is necessary.
• Preferred for the present invention is the phosphosulfurized hydrocarbon polymer of the Loane and Gaynor patent which is derived from polypropene or polybutene polymers of 200 to 4000 M and 5 to 25 weight percent thereon of P 8 reacted at a temperature of -205 C.
• EXAMPLE 1 A mixture of phosphosulfurized polybutene hydrocarbon polymer (polymer fi of 900) having the S:P ratio of 1.65: 1.0 and 25 weight percent thereof of 2,5-bis(octylditho)-1,3,4-thiadiazole is prepared.
• the characteristic pungent, obnoxious odor of said phosphosulfurized polybutene substantially disappeared. After storage of said mixture for seven days, it was noted that the pungent, obnoxious odor was still absent, a small amount of precipitate had appeared and no H 5 (readily detectable in very low concentration) was detected.
• the precipitate was likely a reaction product of some H S (precursor and the bis(alkyldithio)thiadiazole because untreated phosphosulfurized polybutene hydrocarbon stored for seven days did not have any precipitate but did retain not only the pungent, obnoxious odor and did liberate some H S.
• compositions of the present invention to inhibit corrosion of lead and copper-lead bearings is illustrated by the results of a bench test and a test run in an L-38 engine having a Cu-Pb bearings which is a standardized test using leaded gasoline and a SAE-30 grade oil as crankcase lubricant.
• Example 11 1% by weight of phosphosulfurized polypropene (S:P of 1.53:1.0 of Table I) and 0.3% 2,5-bis(octyldithio)-1,3,4-thiadiazole (33% thereof on phosphosulfurized polypropene) or
• Example 12 composition 1% phosphosulfurized polybutene (S:P of 1.5 :1.0 of Table I) and 0.3% 2,5-bis(octyldithio)-l,3,4- thiadiazole (33% thereof on phosphosulfurized polybutene).
• a separate weighed lead strip is immersed in each of the three compositions which are heated to 162- 163 C. for 20 hours while air at 30 ml./min. is injected into the liquid compositions. After such exposure the lead strips are washed with solvent to remove the oil, dried and reweighed to determine weight loss. The results of this bench test are shown in Table IV.
• Example 11 Composition 0
• Example 12 Composition 0 EXAMPLE 13
• the oleaginous crankcase lubricant formulation used in the L-38 Engine Test with new, weighed Pb-Cu bearing is an oleaginous (SAE-30 grade oil) base oil solution consisting of 7.0% detergent-dispersant described for Examples 6-10, 1.7% phosphosulfurized polypropene having S:P ratios of 1.53:1.0 of Table I and 0.3% 2,5-bis(octyldithio)-1,3,4-thiadiazole, 17.65% thereof on phosphosulfurized polypropene.
• SAE-30 grade oil oleaginous (SAE-30 grade oil) base oil solution consisting of 7.0% detergent-dispersant described for Examples 6-10, 1.7% phosphosulfurized polypropene having S:P ratios of 1.53:1.0 of Table I and 0.3% 2,5-bis(octyldithio)-1,3,4-thiadiazole, 17.65% thereof on phosphosul
• the engine piston is inspected and rated for varnish deposit on a scale of 0-10, where O is heavy complete varnish cover and 10 is clean piston.
• the Pb-Cu bearing is washed with solvent to remove oil, dried and reweighed. From this L-38 Engine Test it is found that by the use of above oleaginous crankcase lubricant composition the piston varnish rating is 9.6 (96% clean) and there was a Pb-Cu bearing weight loss of only 33.6 mg. A 50 mg. weight loss is acceptable.
• Example 1 is repeated but using weight percent 2,5- bis(dodecyldithio)-1,3,4-thiadiazole. No precipitate is noted after seven days storage (reaction product with B 8 is soluble) but again the treated phosphosulfurized hydrocarbon polymer had no pungent, obnoxious odor while the untreated phosphosulfurized hydrocarbon polymer has the characteristic pungent, obnoxious odor.
• the method of reducing the characteristic odor and improving the shelf life stability of phosphosulfurized hydrocarbons derived from reaction of P 8 with an alkene hydrocarbon having a molecular weight in the range of 200 to 4000 comprises adding to said phosphosulfurized hydrocarbon from 1.1-50 weight percent thereof of 2,5-bis(alkyldithio)-1,3,4-thiadiazole wherein the alkyl-substituent contains 1-280 carbon atoms.
• said phosphosulfurized hydrocarbon is derived from a liquid, viscous polypropene or polybutene having a number average molecular weight within the range of 200-4000.

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Chemistry (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Engineering & Computer Science (AREA)
• General Chemical & Material Sciences (AREA)
• Lubricants (AREA)
• Compositions Of Macromolecular Compounds (AREA)

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• 1972
  • 1972-10-13 US US00297379A patent/US3826798A/en not_active Expired - Lifetime
• 1973
  • 1973-10-04 AU AU61011/73A patent/AU473525B2/en not_active Expired
  • 1973-10-05 BE BE136414A patent/BE805746A/xx not_active IP Right Cessation
  • 1973-10-09 NL NLAANVRAGE7313853,A patent/NL175309C/xx not_active IP Right Cessation
  • 1973-10-09 DE DE2350622A patent/DE2350622C2/de not_active Expired
  • 1973-10-12 CA CA183,273A patent/CA996101A/en not_active Expired
  • 1973-10-12 IT IT53108/73A patent/IT997654B/it active
  • 1973-10-12 FR FR7336617A patent/FR2202905B1/fr not_active Expired
  • 1973-10-12 JP JP11465173A patent/JPS5419883B2/ja not_active Expired
  • 1973-10-12 GB GB4781973A patent/GB1447097A/en not_active Expired
  • 1973-10-15 LU LU68616A patent/LU68616A1/xx unknown
• 1978
  • 1978-06-07 JP JP6871478A patent/JPS5433505A/ja active Granted

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