US2500167A - Lubricant composition - Google Patents

Description

Patented Mar. 14, 1950 LUBRICANT COMPOSITION William E. Garwood, Haddonfield, Francis M. Seger, Pitman, and Alexander N. Sachanen, Woodbury, N.,J., assignors to Socony-Vacuum Oil Company, Incorporated, a corporation of New York No Drawing. Application June 16, 1948,

- Serial No. 33,438

17 Claims. 1

This invention has to do with the condensation or normal alp 'ia mono-olefins, certain conjugated hydrocarbons and sulfur, and particularly has to do with the new and useful compositions obtained by said condensation.

As is well known to those familiar with the art, olefins have previously been polymerized. So also have conjugated hydrocarbons. Each of these unsaturated materials has previously been reacted individually with sulfur, and olefins and conjugated hydrocarbons have previously been reacted together. In the latter instance, copolymerizationis generally incomplete. For example, when decene-l and styrene are copolymerized at 600 R, an oil containing a polystyrene cloud at room temperature (20-25 C.) is formed. In no known instance, however, have alpha-normal mono-olefins been condensed with conjugated hydrocarbons, of the character defined hereinbelow, and sulfur.

It has now been discovered that normal alpha mono-olefins condense with certain conjugated hydrocarbons and sulfur, under conditions hereinafter defined, with the formation of highly desirable viscous oils. The oils so formed are free from the shortcomings of olefin-conjugated hydrocarbon copolymers, as illustrated by the styrene-decene-l copolymer referred to above. Further, the viscous oils of this invention are unusually stable. Catalytic oxidation stability tests demonstrate them to be superior to condensation products of decene-l alone, and superior tocondensation products of decene-l and styrene. The characteristics of the new oils are such as to make them outstanding synthetic lubricating oils, for use alone or blended with other lubricants.

REACTAN TS As indicated above, the mono-olefin reactants of this invention are normal or straight chain alpha mono-olefins and contain from 5 to 18 carbon atoms. Such mono-olefins are normally liquid at temperatures of the order of 20-25 C. Illustrative of such mono-olefins are the following: pentene-l, octene-l, decene-l, dodecene-l,

octadece e-l, and the like. Preferred, however, of such lefins are those having from 8 to 12 carbon atoms, with decene-l representing a particularly desirable olefin. It will be clear from the foregoing examples that an alpha olefin may also be referred to as a l-olefin.

Not only may the mono-olefins of the aforesaid character be used individually in this invention, but they may also be used in admixture with each other. In addition, olefin mixtures containing a substantial proportion of such mono-olefins may be used. Preferred of such mixtures are those containing a major proportion of a l-olefln or of l-olefins. Rrepresentative of such mixtures are those obtained by the cracking of paraffln waxes and other paraffin products; those obtained from the Fischer-Tripsch and related processes.

These hydrocrabon mixtures may contain, in addition to the l-olefin or l-olefins, such materials as: other olefins, parafiins, naphthenes and aromatics.

The conjugated reactants contemplated herein are conjugated hydrocarbons and derivatives thereof, wherein the conjugated system is represented by the grouping:

Of such conjugated hydrocarbons, butadiene and styrene have been found to be particularly desirable for the purposes of this invention. These conjugated hydrocarbons are characterized by at least one vinyl group,

in a 1:3 conjugated relationship with another double bond. Further examples of such conjugated hydrocarbons are: isoprene (Z-methyl butadiene), l-phenyl butadiene, divinyl benzene, vinyl naphthalene, and the like. Inasmuch as other conjugated hydrocarbons form polymeric materials, as illustrated by cyclopentadiene, methyl isoprene, and the like, such hydrocarbons may also be used to form satisfactory products with the aforesaid l-mono-olefin and sulfur. It will be noted that all of the foregoing conjugated materials are hydrocarbons.

Derivatives of the conjugated hydrocarbons, or substituted conjugated hydrocarbons, which typify those contemplated herein are: halogen-substituted materials such as chloroprene (2-chlorobutadiene), l-bromo butadiene and p-chlorostyrene; alkoxy-substituted materials such as p.-

methoxy styrene; etc. As will be noted from the character of the foregoing typical substituted conjugated hydrocarbons, substituent groups which may be present are those which do not interfere with the course of the condensation of the conjugated system with the aforesaid alphamono-olefln and sulfur. In other words, a substituent group which may be present on the conjugated hydrocarbon is one which is substantially inert or unreactive in the condensation. The substituent group, however, generally modihes the character of the oil product; yet, in all cases, the products are characterized by unusual stability and are useful as lubricants. For example, when chloroprene or p-chloro styrene is used, the synthetic lubricant formed is also characterized by extreme pressure properties.

In connection with divinyl benzene, which may be used as a conjugated reactant, it should be noted that this reactant is characterized by a high degree of reactivity in view of the two vinyl groups. For most satisfactory results with divinyl benzene, a relatively small quantity should be used with a l-mono olefin and sulfur. Accordingly, in the discussion of reaction proportions hereinafter, it should be recognized that the quantity of divinyl benzene used will generally be at the lower end of the conjugated reactant proportion range.

It will be understood, of course, that mixtures of the aforesaid conjugated hydrocarbons, and their aforesaid derivatives, may be used in place of the individual reactant. Similarly, mixtures containing substantial, and preferably major, proportions of one or more of said conjugated reactants may be used. Examples of such mixtures are: a crude-styrene containing ethyl benzene, a crude butadiene containing butenes, and coal tar light oils which contain dicyclopentadiene, indene, coumarone, and aromatics.

As will be evident from the foregoing discussion of the conjugated reactant, benzene is not considered herein as a conjugated hydrocarbon, despite its alternate double bond character. In contrast with benzene, the conjugated reactants, as aforesaid, are characterized by at least one vinyl 8 9 in a 1:3 conjugated relationshi with another double bond.

Preferred of the conjugated reactants are those having only one conjugated grouping with particular preference being given to styrene and butadiene.

As indicated above, sulfur is condensed with the alpha mono-oleflns and conjugated reactants defined above. Also contemplated herein for such condensation in place of sulfur are selenium and tellurium. The latter may replace sulfur in part or in entirety, and mixtures of two or all three of said substances may be used. In view of the availability and low cost of sulfur, and in view of the outstanding character of the oils obtained therewith, sulfur is particularly preferred herein. It is on this basis that the following discussion and illustrative examples are directed to oondensatlons involving sulfur.

REACTION CONDITIONS Condensation of the aforesaid reactants is affected at elevated temperatures. It appears that temperatures as low as 300 F. and as high as- 900" F. can be used in some instances; however, temperatures of the order of about 400 F. to about 750 F. are most satisfactory. The preferred temperature range is from about 600 F. to about 650 F.

Condensation is generally complete in from 1 to 10 hours, with the higher reaction temperatures being used for the shorter reaction periods. and with the lower reaction temperatures being used for the longer reaction periods.

Pressures ranging from atmospheric to 4000 pounds per square inch may be used. In general, it is desirable to use suillcient pressure to maintain the reactants in liquid state.

Proportions of reactants can be varied considerably. With one molar proportion of an alpha mono-olefin as the basis, from about 0.01 to about 1 molar proportion of conjugated reactant and from about 0.001 to about 1 molar proportion of sulfur, provide satisfactory products. Preferred proportions, however, are from about 0.05 to about 0.5 molar proportion of conjugated reactant and from about 0.01 to about 0.5 molar proportion of sulfur, with one molar proportion of alpha mono-olefin.

It will be understood, of course, that the condensation is aided by providing mixing of the reactants. This may be provided b using various agitating means which are well known in the art. At the reaction conditions, the reactants are mutually soluble and homogeneity is easily attained.

- EXAMPLES In order to illustrate the principles of this invention, the results of a series of typical, and nonlimiting, condensations are set forth in tabular form in Table I below. These condensations were carried out in a rocking-type bomb (American Instrument Co.). The reactants were charged to the bomb, which was then heated to the desired temperature for the desired length of time. Thereafter, the bomb was cooled, and discharged. The contents of the bomb were vacuum distilled to remove unreacted materials. It should be noted that the reaction times, recited as Time. hours" in Table I, represent the time intervals during which the bomb was maintained at the desired temperature, and do not include the time intervals necessary to heat the bomb and its contents to the desired temperature, and do not include the time intervals necessary to cool the bomb after heat to the bomb has been discontinued.

The condensation products discharged from the bomb, or other reaction vessel, were distilled and filtered, as in the runs shown in Table I. To distinguish the condensation products from the distillate fractions thereof, the refined oils are identified as residual oils. The latter term identifles the oils from which unreacted materials and products of intermediate boiling range have been separated.

All the tests and analyses to which the residual oils in Table I were subjected are well known standard'tests. In this connection, it will be noted that the designation N. N." refers to the neutralization number, which is a measure of the acidity of the oil.

- Styrene used in these condensations contained a fract on of one per cent of p-tertiary-butyl catechol, the latter acting as a stabilizer or polymerization inhibitor. This styrene material is the commercial product now available.

. um I Cmldenaattcm of olefin: with sulfur and conluaated hydrocarbons Run l 2 3 4 5 0 7 Olefin Deanne-1.. Dooene-L. Decene-L. Decene-l Decline-1.. Decene-L. Deoene-l.

Styrene. Styrene Styrene. 78 26 26.

Mex. Pressure p. e. i. g

Diltlllation 0! Reaction Product:

Mlmvaportem .,"C Pressure, mm.

Residual Oils:

Grams Cloud at Room Temp. (22 0.) gle U. at 210 F 1 Your, '1".. Br. Addn. Refractive Index. S \eciilo Gravitym. 2 .5 0. eroent S 2.57 3.26 0.23 0.85. Distillate, Br No- 87.B 109.23...." 87.0 99.3. ercen 0.93 0059..--.- 0.12.

Decene-L. Decene-l 280.- 366.

G Cloudy at Room Temp. (22 0.). 8. U. at 210 F Br. Addn Refractive Index.

2.0. Styrene. 28

2.0: Styrene. 62

1 292 3. reaction product irom bomb first heated at atmospheric pressure to maximum liquid temperature of 180 0., no distillate.

I Some reaction product lost from bomb. I Adsorbont clay used to improve color, with large loss. Color (Lovibond) carbon residue (Ramsbottom) -0.1.

As can be seen from the data set forth in Table I, above, the omission of sulfur in run-2 resulted in the formation of a resin, and in run 5 resulted in the formation of a product that was cloudy at room temperature (22 C.). In the latter case, the cloud point was actually F., in contrast to cloud points of less than 34 F. for the comparable products of run-6 and run-8.

Evidence that styrene condensed with decene- 1 and sulfur in run-8 is shown by infra-red analysis of the residual oil. Such analysis clearly indicated the presence of aromatic rings in the residual 011. Additional evidence is shown by chemical analysis of the residual oil, the latter containing 0.81 per cent sulfur, 85.99 per cent carbon and 13.11- per cent hydrogen. This anal ysis indicates that the residual oil is composed of 0.81% sulfur, 16.3% reacted styrene (as compared with 8.4% monomer in the charge mixture) and 82.9% reacted decene-l (as compared with 90.9% monomer in the charge mixture).

, rosive sulfur, the latter often being present as loosely-bound sulfur in an oil. In this test, 50 mls. of the oil to be tested are placed in a mls. beaker along with a polished copper strip, about /2 inch by 2 inches. The copper strip is bent into a V and so placed in the beaker that th flat surface thereof does-not touch the bottom or sides of the beaker. The oil sample in the beaker completely covers the copper strip. The beaker, containing oil sample and copper strip, is placed in an electric oven for the required period of time. Thereafter, the beaker is removed from the oven and the copper strip is removed from the beaker. The strip is washed with petroleum ether and then is examined for corrosion. After 26 hours at 100 C., the copper strip subjected to the residual oil from run- 13 was only slightly stained and the oil had only slightly darkened. There was no sludge in the oil sample. This test, then, demonstrates that the sulfur present in the oil is firmly bound and that no free sulfur is present in the oil. It will be noted in Table I, above, that the residual oil from run-13 contains 0.62 percent sulfur.

The stability of the oils of this invention is revealed by the results of a. catalytic oxidation test, to which were subjected several of the residual oils shown in Table I, above. In this test 6.5 feet of No. 14 (Brown and Sharpe gauge) iron wire (15.6 square inch), 6.2 inches of No. 18 (B. I: 8). copper wire (0.78 square inch), 3.33 inches of No. 12 (B. 8: S.) aluminum wire (0.87 square inch), a $4 inch square of inch lead sheet (1% square inch), and 25 ccs. of the test 011 were placed in a glass test tube, heated to 260 F. and air blown therethrough at the rate of liters per hour for 40 hours.

Changes in the characteristics of the oil, sludge formed, and efiects of oil on the copper coil and on the lead sheet were reported. on the basis of these changes, the residual oils were rated as compared with a SAE-IO solvent refined Pennsylvania motor oil subjected to the same test. The results of these tests and of the comparisons obtained in run-13, of .Table I, above, was sub-.

jected to a Lauson oxidation stability test. In this test, a Lauson single cylinder, four-cycle gasoline engine is used. The engine has splash lubrication and a copper-lead bearing. It is operated with an oil temperature of 270 F. and a jacket temperature of 212 F., and a speed of 1825 revolutions per minute (R. P. M.). In the test, the engine is run at one-half throttle, with a 13.0-1 air-fuel ratio. The engine is inspected every hours, with hearing weight loss, engine cleanliness and used oil analyses being reported.

The results of the aforesaid Lauson test are presented in Table III below. In this table, a comparison is shown of R-13 residual oil. and of a blank, an SAE-20 grade Pennsylvania mineral oil which is predominantly paraflinic in character.

TABLE III Lauson OS-Z engine test on sunthetieoil from de cane-1 styrene and sulfur Bearlilggslvgeight Rating Viscosity Insol. in Insol. in Oil Hours N. N. 210 ANS. gt M Otnloro- 1 cs. an t a orm Ovcral Top 2: Clean- Dem liness gency Blank 20 2.2 9. 74 40 4.1 11.00 5.2 11.76 5.3 12.13 5.2 12.00 R-l3 0 0. 2 1 4. 60 20 1.0 v 4.90 40 1.0 5.11 60 2.3 5. 25 80 2.6 5.88 100 2. 5 l 5. 45

1 Viscosity index-120.9, pour point20 F. I Viscosity index-120.3, pour point=25 F.

with SAE-IO Pennsylvania motor oil are reported in Table II below.

TABLE II Catalytic oxidation test .Run

Time, Hours Sludge Tube Copper Coil Load L05, Mgm Rated Against Nil Equal"...

Worse Equal...

1 Indicates oil is very bad in this factor and would probably fail in an engine test.

From inspection of the results shown above in Table II, it will be seen that in every instance the new synthetic oils are equal to or better than SAE-IO Pennsylvania motor oil in every less for the residual 011, 59-13, than for the blank oil. The average loss for the top and bottom sections of the bearing in contact with the blank oil is 0.491 gram, as compared with only 0.085 gram when the oil is 12-13 residual oil. Consistent with this comparison is the large differences in N.N. values for the two oils. While the engine cleanliness rating for R-13 residual oil is somewhat lower than the rating for the blank oil, it is of the same order as the blank oil when the latter contains a small amount of a conventional antioxidant (which tends to make for lowered cleanliness rating). The blank oil requires such an anti- 1 oxidant to prevent bearing loss and thus meet present day lubricant requirements. It will also be noted that the viscosity change of 12-13 residual oil over the 100 hour period is only 18 per cent, as against a 23 per cent change for the blank oil. Finally, it should be noted that R 13 residual oil has a low initial pour point, 20 F., and at the end of the test still has a low pour point, -25 F. This demonstrates that the oil does not undergo reversion of pour point, which is a serious problem today with oils'of the type of the blank, particularly when the latter contains certain of the commercially available pour point depressants.

As will be evident from the data presented above in Tables I, II and III, the condensation products of this invention are highly desirable lubricants per se. They are also of considerable value as blending agents for other lubricating oils. In view of the inherent stability of the synthetic oils, they impart stability to the oils with which they are blended. So also, they impart desirable viscosity index (V. I.) and pour point characteristics to the oils in combination therewith, for, as indicated above, they have advantageous vis cosity index and pour point properties. In short, the synthetic oils find utility in upgrading other lubricants. Typical oils with which the synthetic oils may be blended are mineral oils such as are normally used in internal combustion and turbine engines. When so blended, the synthetic oils may comprise the major proportion of the final blended oil, or may even comprise a minor proportion thereof. For example,

although used only in the amounts of the order of 1 to per cent, the synthetic oils improve the stability of mineral oils, such as SAE 10 and 20 Pennsylvania type oils.

One or more of the individual properties of the synthetic lubricants of this invention may be further improved by incorporating therewith a small, but effective amount, of an addition agent such as a detergent, an extreme pressure agent, a foam suppressor, a viscosity index (V. I.) improver, etc. Typical detergents which may be so used are metal salts of alkyl-substituted aromatic sulfonic or carboxylic acids, as illustrated by diwax benzene barium sulfonate' and barium phenate, barium carboxylate of a wax-substituted phenol carboxylic acid. Extreme pressure agents are well known; illustrating such materials are numerous chlorine and/or sulfur containing compositions, one such material being a chlornaphtha xanthate. Silicones, such as dimethyl silicone, may be used to illustrate foam suppressing compositions. Viscosity index improving agents which may be used are typified by polypropylenes, polyisobutylenes, polyacrylate esters, and the like.

contemplated also as within the scope of this invention is a method of lubricating relatively moving surfaces by maintaining therebetween a film consisting of any of the aforesaid oils.

It is to be understood that the foregoing description and representative examples are nonlimiting and serve to illustrate the invention,

10 which is to be broadly construed in the light of the language of the appended claims.

We claim:

1. The method of preparation of a viscous oil, which comprises: condensing, at a temperature between about 400 F. and about 750 F. for a period of time from about ten hours to about one hour, respectively, one molar proportion of a straight chain, alpha mono-olefin having from 5 to 18 carbon atoms per molecule, from about 0.01 to about one molar proportion of a conjugated -hydrocarbon and from about 0.001 to about one molar proportion of a substance selected from the group consisting of sulfur, selenium and tellurium; said conjugated hydrocarbon being characterized by at least one --(.'=c-o=o- I I I I grouping and being selected from the group consisting of conjugated hydrocarbons and substituted conjugated hydrocarbons wherein a substituent is one which is substantially inert in said condensation.

2. The method of preparation of a viscous oil, which comprises: condensing, at a temperature between about 400 F. and about 750 F. for a period of time fromabout ten hours to about one hour, respectively, one molar proportion of a straight chain, alpha mono-olefin having from five to eighteen carbon atoms per molecule, from about 0.01 to about one molar proportion of a conjugated hydrocarbon and from about 0.001 to about one molar proportion of sulfur; said conjugated hydrocarbon being characterized by at least one -o=o-o=c I I I I grouping and consisting essentially of the elements carbon and hydrogen.

3. The method of preparation of a viscous oil, which comprises: condensing at a temperature between about 400' F. and about 750 F. for a period of time from about ten hours to about one hour, respectively, one molar proportion of a straight chain, alpha mono-olefin having from five to eighteen carbon atoms per molecule, from about 0.01 to about one molar proportion of a substituted conjugated hydrocarbon and from about 0.001 to about one molar proportion of sulfur; said conjugated hydrocarbon being characterized by at least one c=o-o=o I I l I grouping and having a halogen substituent.

4. The method of preparation of a viscous oil, which comprises: condensing, at a temperature between about 400 F. and about 750 F. for a period of time from about ten hours to about one hour, respectively, one molar proportion of a straight chain, alpha mono-olefin having from five to eighteen carbon atoms per molecule, from about 0.01 to about one molar proportion of a substituted conjugated hydrocarbon and from about 0.001 to about one molar proportion of sulfur; said conjugated hydrocarbon being characterized by at least one c=c-c=o I I I grouping and having an alkoxy substituent.

5. The method of preparation of a viscous oil, which comprises: condensing, at a temperature between about 400 F. and about 750 F. for a period of time from about ten hours to about one hour, respectively, one molar proportion of a straight chain, alpha mono-olefin having from eight to twelve carbon atoms per molecule, from about 0.01 to about one molar proportion of a conjugated hydrocarbon and from about 0.001 to about one molar proportion of sulfur; said conjugated hydrocarbon being characterized by at least one -c=o-o=e I I I I grouping and consisting essentially of the elements carbon and hydrogen.

6. The method of preparation of a viscous oil, which comprises: condensing, at a temperature between about 400 F. and about 750 F. for a period of time from about ten hours to about one hour, respectively, one molar proportion of a straight chain, alpha mono-olefin having from five to eighteen carbon atoms per molecule, from about 0.01 to about one molar proportion of a conjugated hydrocarbon and from about 0.001 to about one molar proportion of sulfur; said conjugated hydrocarbon being characterized by one -c=o-o=c- I I I l grouping and consisting essentially of the elements carbon and hydrogen.

7. The method of preparation of a viscous oil, which comprises: condensing at a temperature between about 600 F. and about 650 F. for a period of time from about ten hours to about one hour, respectively, one molar proportion of a straight chain, alpha mono-olefin having from five to eighteen carbon atoms per molecule, from about 0.01 to about one molar proportion of a conjugated hydrocarbon and from about 0.001 to about one molar proportion of sulfur; said conjugated hydrocarbon being characterized by at least one -o=c-c=c I l l I grouping and consisting essentially of the elements carbon and hydrogen.

8. The method of preparation of a viscous oil, which comprises: condensing, at a temperature between about 400 1". and about 750 F. for a period of time from about ten hours to about one hour, respectively, one molar proportion of a straight chain, alpha mono-olefin having from five to eighteen carbon atomsper molecule, from about 0.05 to about 0.5 molar proportion of a conjuagated hydrocarbon, and from about 0.01 to about 0.5 molar proportion of sulfur; said conjugated hydrocarbon being characterized by one I l I grouping and consisting essentially of the elements carbon and hydrogen.

9. A condensation product obtained by: condensing, at a temperature between about 400 F. and about 750 F. for a period of time from about ten hours to about one hour, respectively, one molar proportion of a straight chain, alpha mono-olefin having from live to eighteen carbon atoms per molecule, from about 0.01 to about one molar proportion of a conjugated hydrocarbon and from about 0.001 to about one molar proportion of a substance selected from the group consisting of sulfur, selenium and tellurium; said conjugated hydrocarbon being characterized by at least one I I I I grouping and being selected from the group consisting of conjugated hydrocarbons and substi- 12 tuted conjugated hydrocarbons wherein a substituent is one which is substantially inert in said condensation.

10.A condensation product obtained by: condensing, at a temperature between about 400' F. and about 750 F. for a period of time from about ten hours to about one hour, respectively, one molar proportion of a straight chain, alpha mono-olefin havingfrom five to eighteen carbon atoms per molecule, from about 0.01 to about one molar proportion of a conjugated hydrocarbon and from about 0.001 to about one molar proportion of sulfur; said conjugated hydrocarbon being characterized by at least one -c=c-c=o- I I I l grouping and consisting essentially of the elements carbon and hydrogen.

11. A condensation product obtained by: condensing, at a temperature between about 400 F. and about 750 F. for a period of time from about ten hours to about one hour, respectively, one molar proportion of a straight chain, alpha mono-olefin having from eight to twelve carbon atoms per molecule, from about 0.01 to about one molar proportion of a conjugated hydro.- carbon and from about 0.001 to about one molar proportion of sulfur; said conjugated hydrocarbon being characterized by at least one C=C Q=C I l I I grouping and consisting essentially of the elements carbon and hydrogen.

12. A condensation product obtained by: condensing, at a temperature between about 400 F. and about 750 F. for a period of time from about ten hours to about one hour, respectively, one molar proportion of a straight chain, alpha monoolefln having from five to eighteen carbon atoms per molecule, from about 0.01 to about one molar proportion of a conjugated hydrocarbon and from about 0.001 to about one molar proportion of sulfur; said conjugated hydrocarbon being characterized by one grouping and consisting essentially of the elements carbon and hydrogen.

13. A condensation product obtained by: condensing, at a temperature between about 600 1''. and about 650 F. for a period of time from about ten hours to about one hour, respectively, one molar proportion of a straight chain, alpha monoolefln having from five to eighteen carbon atoms per molecule, from about 0.01 to about one molar proportion of a conjugated hydrocarbon and from about 0.001 to about one molar proportion of sulfur; said conjugated hydrocarbon being characterized by at least one C=Q-C=C I l l I grouping and consisting essentially of the elements carbon and hydrogen.

14. A viscous oil composition comprising a mineral oil of lubricating viscosity in major proportion and a minor proportion, from about one to about ten per cent, of a condensation product; said condensation product being obtained by: con. densing, at a temperature between about 400 F. and about 750 F. for a period of time from about ten 'hours to about one hour, respectively, one molar proportion of a straight chain, alpha monoolefln having from five to eighteen carbon atoms per molecule, from about 0.01 to about one molar four molar proportions of styrene and one molar proportion of sulfur.

16. A condensation product of lubricating viscosity obtained by: condensing, at a temperature of about 600 F. for about ten hours and with a pressure of about 250 pounds per square inch, about four molar proportions of decene-l, about one molar proportion of styrene and one molar proportion of sulfur.

17. A condensation product of lubricating vis cosity obtained by: condensing, at a temperature of about 600 F. for about ten hours and with a pressure 01' about 200 pounds per square inch, about sixteen molar proportions of decene-l, about four molar proportions of butadiene and one molar proportion of sulfur.

WILLIAM E. GARWOOD. FRANCIS M. SEGER. ALEXANDER N. SACHANEN.

REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Number Name Date 2,213,423 Wiezevich Sept. 3, 1940 2,337,473 Knowles Dec. 21, 1943 2 2,439,610 Morris et a1 Apr. 13, 1948 2,442,644 Elwell June 1, 1948

Claims (2)

1. THE METHOD OF PREPARATION OF A VISCOUS OIL, WHICH COMPRISES: CONDENSING, AT A TEMPERATURE BETWEEN ABOUT 400*F. AND ABOUT 750*F. FOR A PERIOD OF TIME FROM ABOUT TEN HOURS TO ABOUT ONE HOUR, RESPECTIVELY, ONE MOLAR PROPORTION OF A STRAIGHT CHAIN, ALPHA MONO-OLEFIN HAVING FROM 5 TO 18 CARBON ATOMS PER MOLECULE, FROM ABOUT 0.01 TO ABOUT ONE MOLAR PROPORTION OF A CONJUGATED HYDROCARBON AND FROM ABOUT 0.001 TO ABOUT ONE MOLAR PROPORTION OF A SUBSTNACE SELECTED FROM THE GROUP CONSISTING OF SULFUR, SELENIUM AND TELLURIUM; SAID CONJUGATED HYDROCARBON BEING CHARACTERIZED BY AT LEAST ONE

14. A VISCOUS OIL COMPOSITION COMPRISING A MINERAL OIL OF LUBRICATING VISCOSITY IN MAJOR PROPORTION AND A MINOR PROPORTION, FROM ABOUT ONE TO ABOUT TEN PER CENT, OF A CONDENSATION PRODUCT; SAID CONDENSANTION PRODUCT BEING OBTAINED BY: CONDENSING, AT A TEMPERATURE BETWEEN ABOUT 400*F. AND ABOUT 750*F. FOR A PERIOD OF TIME FROM ABOUT TEN HOURS TO ABOUT ONE HOUR, RESPECTIVELY, ONE MOLAR PROPORTION OF A STRAIGHT CHAIN, ALPHA MONOOLEFIN HAVING FROM FIVE TO EIGHTEEN CARBON ATOMS PER MOLECULE, FROM ABOUT 0.01 TO ABOUT ONE MOLAR PROPORTION OF A CONJUGATED HYDROCARBON AND FROM ABOUR 0.001 TO ABOUT ONE MOLAR PROPORTION OF SULFUR; SAID CONJUGATED HYDROCARBON BEING CHARACTERIZED BY AT LEAST ONE