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
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
• • 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
  • C10M2201/04—Elements
  • C10M2201/041—Carbon; Graphite; Carbon black
• • 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
  • C10M2201/04—Elements
  • C10M2201/041—Carbon; Graphite; Carbon black
  • C10M2201/042—Carbon; Graphite; Carbon black halogenated, i.e. graphite fluoride
• • 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
  • C10M2201/04—Elements
  • C10M2201/043—Sulfur; Selenenium; Tellurium
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/102—Aliphatic fractions
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/104—Aromatic fractions
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/106—Naphthenic fractions
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/108—Residual fractions, e.g. bright stocks
• • 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
  • C10M2207/40—Fatty vegetable or animal oils
• • 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
  • C10M2207/40—Fatty vegetable or animal oils
  • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
• • 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
  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
  • C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
• • 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
  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/06—Perfluorinated 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
  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/08—Halogenated waxes
• • 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
  • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/083—Dibenzyl sulfide
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/20—Metal working
  • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2070/00—Specific manufacturing methods for lubricant compositions
  • C10N2070/02—Concentrating of additives

Definitions

• the present invention relates to a cutting oil concentrate, cutting oils containing such a concentrate and characterized by a unique combination of superior cutting ability and absence of the formation of disagreeable odors when in use, and to a method of making the concentrate.
• Oils containing sulfur or sulfur compounds dissolved therein have been suggested heretofore as cutting oils. Such oils also frequently contain chlorine and a fat such as lard oil. It is believed that the sulfur, to be effective in improving the cutting ability of a cutting oil, must be.
• odor characteristics of a cutting oil are not necessarily apparent upon an examination of the oil as produced or supplied to a user. are developed only when the oil is used in machining operations. This is apparently due to the formation of odoriferous compounds under the conditions prevailing at the cutting tool. If the cutting oil develops an unpleasant or obnoxious odor during use, it makes no difference how good the oil is from the standpoint of cutting ability, i. e., the number of pieces that can be machined with a given tool, the wear on the tool and the surface finish of the metal being machined because machinists will refuse to work with it.
• Hydrocarbon polysulfides containing one or more alkyl or aryl radicals have been suggested as being suitable for In many instances, odorsitself rather than of a mercaptan impurity, since it cannot be altered by caustic washing, and diallyl tetrasulfide which, because of its light yellow color, ready miscibility with mineral oil and very high sulfur content appeared very promising, was found to have a nauseating garlic odor.
• the few polysulfides in this group that do not possess such odors initially, almost without exception develop odors, upon use, that are or soon become so obnoxious as to cause machinists to walk off the job.
• aryl sulfides in cutting oils relate generally to those aryl sulfides in which a sulfur atom or a chain of sulfur atoms is substituted directly on the aromatic nucleus.
• aryl sulfides such as phenyl-, tolyl-,
• the method of the invention' comprises re 5 ';acting a mixture containing one or more alkyl-substituted 1y unpleasant odor that is characteristic of the polysulfide .sulfur at an elevated temperature.
• benzyl monohalides and one or more alkyl-substituted xylylene dihalides the benzyl halides and xylylene dihalides being present in a molal ratio greater than 2:1
• reactants may all be mixed together and reacted in a single step. It is" preferred, however, first to react a benzyl monohalidexylylene dihalide mixture with an alkali-metal polysulfide to form the corresponding xylylene di-polysulfides,, or a mixture thereof with alkyl-substituted benzyl polysulfides containing an average of at least about three and preferably about four sulfur atoms per sulfur bridge.
• These compounds and mixtures are highly useful as cutting oil concentrate but are then preferably reacted with elemental sulfur to form stable products containing an average of between about four and five, and preferably close to fivesulfur atoms per sulfur bridge.
• a catalytic reformate containing primarily the various isomers of trimethylbenzene and methylethylbenzene, as Well as some propylbenzenes and less heavily substituted alkylbenzenes, is chloromethylated by any suitable means such as, for example, by reaction with formaldehyde, or a formaldehyde engendering material, and HCl in the form of hydrochloric acid, hydrogen chloride gas, or both for from about two to about seven hours at temperatures of the order of about 150 F.
• This reaction is advantageously carried out while stirring the reactants under a reflux and, after the reaction is complete, cooling the reaction mixture to room temperature, separating the two immiscible phases, washing the oily layer with water and separating the aqueous phase, washing the layer with sodium carbonate solution until the products are neutral, separating the layers, washing the products again with water and separating the layers, and finally drying the products with anhydrous calcium chloride.
• the organic reaction product thus obtained is essentially a mixture of alkyl-substituted xylylene dichlorides having a total of eleven carbon atoms, i.
• the molal ratio of the benzyl monochlorides to the xylylene dichlorid'es is normally at least about 3:1.
• Lower ratios, e. g., 2.88:1 have however been obtained with the same starting material by using a considerable excess of HCl in the form of a gas in the chloromethylation.
• the aqueous phase is separated and the remainder, i. e., the organic phase, is washed with alkali-metal hydroxide solution by stirring for about one-half hour atllO to 120 F. and, if desired,'treated witha mineral adsorbent.
• alkali hydroxide solution whichforms a lower .1 layer
• high yields are obtained of a composition comprisingprimarily di-polysulfides having the formula in which the Rs stand for alkyl-substituted benzyl radicals having ten carbon atoms, R stands for an alkylsubstituted xylylene radical having eleven carbon atoms, and x is an average of at least about 3 and generally about 4.
• these compounds are referred to herein as the xylylene di-tetrasulfides or the trimers.
• oil-soluble organic products of reaction with sodium tetrasulfide are probably mixtures of one or more of the described xylylene di-tetrasulfides with alkyl-substitutcd benzyl tetrasulfides.
• the molal ratio of monochlorides to dichlorides reacted with sodium tetrasulfide is about 3:1
• the molal ratio of the xylylene di-tetrasuliides to the benzyl tetrasulfides is about 2:1.
• the reaction between the halides and alkali-metal polysulfide is preferably carried out in the presence of a diluent having a low viscosity and a high flash point.
• Hydrocarbon fractions having boiling points ranging from the kerosene to the fuel oil boiling ranges, generally designated as gas oil, are particularly suitable for this purpose.
• gas oil or fuel oil which does not react with either the reactants, the alkyl-substituted xylylene and benzyl tetrasulfides or the ultimately desired alkyl-substituted xylylene and benzyl pentasulfidcs, has the highly desirable and purely physical functions of imparting to the mixture thereof lower viscosities than either the tetrasulfides or the pentasulfides per se, facilitating the handling of the reactants and the products, and aiding in the separation of any aqueous phase after the reaction.
• Alkyl-substituted benzenes having boiling points above about 300 F. such as any that may be unreacted in the chloromethylation described, are, like the dimers, also eminently suitable as diluents.
• the diluent remains with the organic phase and serves as such in the succeeding reaction step with elemental sulfur.
• the tetrasulfides obtained by reaction of the benzyl monochlorides and xylylene dichloridcs with sodium polysulfide are then reacted, preferably under an inert atmosphere such as nitrogen and while remaining in the presence of the diluent, with an excess, preferably about 5%, of elemental sulfur for two to three hours at a temperature between about 200 F. and about 300 F., preferably about 240 F., to form the corresponding pentasulfides, :so referred to herein because they contain an average of close to five sulfur atoms between adjacent aryl groups.
• the polysulfide content of the concentrate may be entirely alkyl-substituted xylylene di-polysulfide or it may be an admixture of as little as about one mol of the dipolysulfide, i.
• trimer to nine mols of alkylsubstituted benzyl polysulfide, i. e., the dimer.
• Both the tetraand pentasulfides of the invention may be blended to form stable and clear solutions with any mineral cutting oil base, preferably an acid-treated oil having a viscosity between about 75 and 300 SSU at 100 F., and said cutting oil base may itself contain free sulfur dissolved therein.
• a suitable hydrocarbon diluent such as gas oil
• any mineral cutting oil base preferably an acid-treated oil having a viscosity between about 75 and 300 SSU at 100 F.
• said cutting oil base may itself contain free sulfur dissolved therein.
• the lower limit of viscosity specified is imposed largely by sulfur solubility. Oils having viscosities higher than 300 SSU at 100 F. are not preferred because of dificulties of handling and flowing.
• Cutting oil blends containing as little as 0.5% or less by weight of alkylsubsti-tuted xylylene di-tetrasulfide or di-pentasulfide have excellent cutting ability.
• the concentrates of the invention and the cutting oil blends containing the concentrates combine this unusually excellent cutting ability with low volatility, ability to stay on the tool and the work at the cutting point even at high temperature, absence of ob-v jection-able odor either upon standing or in severe use and ability to form stable blend with cutting oil bases.
• sulfurized oil blends containing between about 0.5% and 5% by weight of the concentrate are highly satisfactory.
• the most surprising characteristic of the cutting oil concentrates of the invention is that they make it possible to incorporate into a cutting oil blend more active sulfur than is required or desired for some types of cutting operations.
• the present invention therefore, provides an excellent means of controlling accurately the amount of active sulfur in a cutting oil so that it will be the optimum amount for any particular metal cutting operation. It is also possible to add small amounts of other ingredients, e. g., 1% by volume lard oil, that mask the effect of excess sulfur.
• the products of this invention consist essentially of one or a combination of the named alkyl-substituted xylylene di-polysulfides, preferably diluted witth alkyl-substituted benzyl polysulfides or unsulfurized gas oil or both, and blended or not with a mineral cutting oil base
• conventional additives such as lard oil, graphite, and oil soluble chlorinated compounds such as chlorinated wax and chlorinated aromatics typical of which is chlorinated biphenyl and the like may be added in amounts that do not materially alter the character of the products. It is also within the scope of the invention to add minor proportions, i. e.,
• the blending of the cutting oil of the invention with lard oil in an appreciable amount, i. e., above about 1%, and preferably from about 2 to by volume, is particularly desirable and advantageous for reducing tool wear when cutting operations are carried out on abrasive steels and has the further advantage of providing a cutting oil that is most universally useful on both abrasive steels and ductile steels.
• a preferred cutting oil is a blend of a mineral cutting oil base with about 4% by volume of lard oil and about 1%- by weight of a 60/40 mixture of the xylylene polysulfide and gas oil.
• methylethylbenzene isomers (20% l-methyl-3-ethylbenzene, 8% l-methyl-4-ethylbenzene, 8% 1-methyl-2-ethylbenzene), 3% isopropylbenzene and minor amounts of m-xylene (3%), o-xylene (6%), p-xylene (trace) and 13% unidentified monoalkylbenzenes probably including propylbenzene isomers, were refluxed at 140 to 158 F.
• Part B 162.2 parts by weight of the above-described approximately 3:1 molal mixture of benzyl monochlorides and Solvesso 100, were admixed with 244 parts by weight of a 40% aqueous solution of sodium tetrasulfide and with 152 part by weight of a gas oil having a viscosity of 42 SSU at F. and a flash point at 275 F. The mixture was subjected to reflux at 200 F. for about five to six hours while stirring well. The reaction mixture was then cooled to about 120 F.
• This concentrate was found, upon analysis, to have a total sulfur content of 14.0% and an active sulfur content of 7.1%, indicating that the sulfur bridges in the .polysulfide contains an average of approximately four sulfur atoms.
• Part C 330 parts by weight of the 46% concentrate prepared in accordance with part B of the example were admixed with 12.85 parts by weight of sulfur and sufficient additional gas oil to maintain the ratio of polysulfide to gas oil at about 46/54. The mixture was then stirred for two hours under nitrogen atmosphere at a temperature of 240 F.
• the yield of sulfurized concentrate was practically quantitative, the total sulfur content being 18.0% and the active sulfur content being 11.0%, indicating that the sulfur bridges in the polysulfide contain an average of about five sulfur atoms.
• Part D A cutting oil base was prepared by adding to Diamond Paratiin oil, an acid-treated lubricating oil stock having a viscosity of 100 SSU at 100 F., 0.8% by weight elemental sulfur, i. e., the maximum amount of sulfur soluble in the oilat C. The mixture was heated and stirred at 200 'F. until all of the sulfur was dissolved. This took approximately one to two hours.
• Blends of the cutting oil base with 0.5 to by weight of the 46/54 concentrate prepared in part B of the example and with 0.5 to 5% by weight of the 46/54 concentrate prepared in part C of the example form excellent cutting oils'characterized by remarkable cutting ability, low volatility and absence of odor, and ability to remain on the work and the tool at the point of cut.
• tie rods were made from C-1022 steel forgings. The finish was taken as the criterion of tool life, which was considered an end when either tearing of the thread flank and crest or chip welding at the root of the chaser land occurred. In these tests, as many as 2100 tie rods were threaded before tool failure.
• the product of the invention can also be prepared, with improved yield, by the method described in copending application Serial No. 455,748, filed September 13, 1954, now abandoned.
• a cutting oil concentrate comprising from about 50 to about 70% by weight of a mixture of organic dipolysulfides having the formula CiH5 CzHs
• a cutting oil concentrate comprising from about 50 to about 70% by weight of a mixture of organic dipolysulfides having the formula R1 R: It:
• R1, R2 and Rs are selected from the group consisting of three methyl radicals, one methyl and one ethyl radical, and one propyl radical, and x is at least 3, and from about 50 to about 30% by weight of a hydrocarbon diluent.
• a cutting oil concentrate comprising from about 50 to about 70% by weight of a mixture of organic dipolysulfides having the formulae ant-arcing) (CH3): H3):
• CHr-S -C1-I2 and the formulae Gout-spont- D op CH: CH;
• R1, R2 and R3 are selected from the group consisting of three methyl radicals, one methyl and one ethyl radical, and one propyl radical, and x averages at least about 3.
• a cutting oil comprising a mineral oil containing up to about 0.8% free sulfur dissolved therein and from about 0.5 to about 5% by weight of a mixture of organic dipolysulfides having the formula @CHa-SrCHa-Q-CIHa-BrCHTQ R1 R2 R3 where R1, R2 and Rs are selected from the group consisting of three methyl radicals, one methyl and one ethyl radical, and one propyl radical, and x averages between about 4 and '5.
• a cutting oil comprising a mineral oil and from about 0.5 to about 5% by weight of a mixture of organic dipolysulfides having the formula R1 R: R3
• R1, R2 and Rs are selected from the group consist ing of three methyl radicals, one methyl and one ethyl radical, and one propyl radical, and x is at least aboutB, and the molal ratio of benzyl xylyl polysulfides to benzyl polysulfides being about 2:1.

Landscapes

• 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)

Priority Applications (5)

Applications Claiming Priority (1)

Publications (1)

Family

ID=23810125

Family Applications (1)

Country Status (5)

Families Citing this family (5)

Citations (1)

• 0
  • BE BE541222D patent/BE541222A/xx unknown
• 1954
  • 1954-09-13 US US455747A patent/US2790774A/en not_active Expired - Lifetime
• 1955
  • 1955-09-07 FR FR1135980D patent/FR1135980A/fr not_active Expired
  • 1955-09-12 GB GB26072/55A patent/GB790568A/en not_active Expired
  • 1955-09-12 CH CH338541D patent/CH338541A/de unknown

Patent Citations (1)

Also Published As

Similar Documents