CA1044226A - Sulfur-containing compositions - Google Patents

Abstract

Compositions suitable as replacements for sulfurized sperm oil as extreme pressure additives in lubricants are obtained by sulfurizing a mixture of at least one fatty acid ester (preferably an oil such as soybean oil), at least one C8-36 aliphatic olefin (preferably an .alpha.-olefin), and at least one fatty acid (preferably unsaturated).

Description

9~

Thi9 inv0ntion r~latQs to new compositio2ls of matter suitab~e for use a~: lubricant additives J and to m~thod~ for their preparati~n.. More pax~icularly, i~ relate~ to ~ulfuriz~d compc>sition~ prepared by re~c:ting~ at about 100-25QC., sulfur with a mixt~lre comprising (A) 100 part~ by wei-3ht of at 1~3a~t on~ fatlty ac~id e3ter, (B) about P-50 parts by weight of at least one fatty acid, and (~) about 25~400 parts by weight of ~- a~ l~ast one aliphatic olefin containing about 8-36 ~arbon atoms .
Sulfuriæed ~perm oil ha~ long been used a~ a l~ibrican~
additive, parti~ularly to improve extrerne presæure propertie~
while providirlg exs:ellent ~lip~ and ~ome degree of rust inhibition in mator oil~, gear lubric~nts~ cutting and rolling oil~ owev~r, the United State~ Govexnme~3t has r~cently . taken a~tion to preverlt the killing of w~ale~s, ~rom which ~perm oil is obtained, to avoid their beconnin~ extinct~ The only ~our~e o~ ~perm oil ha3 the~efore "dried up" and it ha~ become nece~ary to find substitutes fcsr the sulfurized derivative ~hereof, whic~ can b~ cheaply and e~Eficiently produaed and which provide the same advantageous properties to lubri~:ant~.
A prin~:ipal ob~ect o:~ the present invention, therefore, 3 i8 to provide a method for producing useful lubricant additive~ .
A ~u~ther ob~ect i~ to produce sulfurized lubricant additives whic~h improve extreme presslLre propertie~.
Still arlother object i5 to produ~e composi~ions which may be sub~tituted for suluri2ed ~perm oil as lubricant ad~itives, and which provide l:he same properties as the ~perm oil derivative.

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:,~'' . , . -~, f $f / ~ f~
other ob~ect~ will in par~ be obvious and will in par~ appear hereina~ r.
As previously describedg th~ method of ~hi~ înren~ion comprise~ the reaction of sul*ur with a mixture of three xeagent~., Reagent A is at least c3ale fatty acid ester~ ~he term " fatty acid" as ~a~ed har6~in refers to acids which may be obtained :by hydroly~is of a rlaturally occurring ~egetable or animal f~at or oil ~. The~e are u~ ally in ~he C16 ~20range and include palmitic at:id, ~tearic acid, oleic acid, linoleic:
10 acid a~ad the liXe.
Fatty ac:id esters w~ich are use:Eul as Reagent A are primarily tho~e ~ith aliphatic alcohol~ cluding monohydric alcohols sue:h a~ methanol~ ethanol, n-propanolJ isopropanolg the butanol~, et~g and p~yh~dric alcohols including e~hylene ~:
glycol, propylene glycol, trime hylene glycol, neopelltyl glycol, glys:erol and the like. Particularly preferred axe the ~atty oil~, that i8 9 naturally occur~ing esters o~ glycerol with the above-noted long c:hain carboxylic acids, and ~ynthetic es er~ of 8i~ ar structure. Still more preferred are fatty oil derived 20 ~rom un~a~urated acids, e~peaially oleic and linoleic, includin ~uch naturally oc~urring aninE~l and vegetable oils as lard oil, peanut oil, cottonseed oil, soybean oil, corn oil, and the li~e.
Reagent B is at least one fatty acid as de~cribed Te. It is u~ually an un3aturated fatty ac:id ~uch as oleic o~ linoleic acid, and may be a mixture o~E acids such as i~
obtained ~rom tall oil or by the hydrolysi~ of peanut oilt soybean oil or the likeO The a~ount o~ Reage~t B is about

2-50 partæ by weight p~r 100 part~ of reag2nt A. Reagen~ ~3 ~', z~
ha~; the impor~ant function that it improves the "slip", rust inhibi~ing and extreme pres~ure propertie~ of lub:ricants containing the ~;ulfurized compt~sitions oi~ thi~ invention, and so it~ pre~er~ce (pr~3f~rably in the amowlt o~ about 2-8 parts by weight) is h~g~ly advantageous.
~ eage~t C i-~ at lea~t one Cg-36 aliphatic olefin.
About 25-400 parts, u~ually a~out 25-75 parts, of re~en'c C
are present per 100 parts of reagent A. Terminal olefins, or a-ol~ins, are ~ ferred~ e~pecially tho~e in C12-20 range.
10 Mixture~ of these ole~ins are ~ommerc~ ally availa}~le and ~;uch mix~ures ar0 contem~late~ ~or u~ in th ~ invent;ion.
In addit~n to the al~ove-deseribed reagents, the rea~:tio~ mixture may cc~ntain other materialæ. The3e m~y include, for example, sulfurization promoter~, typi~ally ; pho~phoru~-containi~g reagent~ su~h as phosphorou~ a~id ester~ (e.g., triphsnyl phosphite), and ~urface active agent3

3 such as le~i~hin.
~he method of this invention compri~es the r~action o~E
a mixture of the above-noted reagents with sulfur at a , 20 tamperatur~ of about 1~0-250C., usually about 150-210C.
~he weight ~atio of the co~ination o~ reagents A, B and C
to sul~ between about 5:1 and 15:1, generally between about 5 :1 and 10 ~
he ~ulfurization reaction is e~fected by merely heating the reagent~ at ~he ~emperature indicat~3d a:bove, usually with e:eficien~ agita~ion and in an inert a1:mo~phere (e.g., nit~ogen) i I~ a~y o~ the reagent~, e~pecially xeagent C, are appreciably volatile at the reaction t:e~nperature, ~he reaction vessel may be sealed and maintained under pre~slare~ It i5 reS~uently 30 advanta~geou~ to add the ~ulfur ...

portionwise to the mixture of th~ other reagents. I~lhlle it is usually preferred that the reac-tion rnixture consist entirely of the r~agents previously described, the r~action ; Illay al90 be effected in the presence o~ an inert solvent (e.g., an alcohol, ether, ester, aliphatic hydrocarbon~
halogenated aromatic h~drocarbon or the like) which is .. .
liquid within the temperature range employed. When the reaction temperature is relatively high, e.g. J about 200C., there may be some evolution of sul~ur ~rom the product which is avoided i~ a lower reaction temperature (eOg., about 150-170~C.) is used. However, the reaction sometimes :: ~
requires a longer tim~-at lower temperatures and an adequate sulfur content is usually obtained when the temperature is at the high end of the recited range.
Following the reaction, insoluble by-products ma~
be removed by filtration, usually at an elevated temperature (about 80-120C~). The ~iltrate is the desired sulfuri~ed product, In general~ products prepared as described above and containing about 8-13~ (by weight) sulfur are pre~erred for the purposes of this invention. It may sometimes be desirable, however~ to employ products containing more sulfur, typically about 13-16~ by weight. Also, it has been found that a product having improved solubility in bright stocks may be obtained by preparing B high~sulfur product of this type and diluting the sa~e with a fatty ; oil such as lard oil to obtain a product having a lower sulfur content.
The method o~ this invention is illustrated by the followlng examples. All parts are by weight.

~4~ _ . .

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~' Examp]e 1 A rnix~ure of 60 parts of cor~nercial Cls-20 a-olefins and 100 parts o~ lard oil is heated to 160C., under nitrogen~ and 1~ parts o~ sulfur is addedO The mixture is heatecl at 1.65-200C, and an additional 6. 5 parts of sulfur is added Heating is continu~d ~or 4 hours, after which the mixture is cooled to 100C. and filtered to yield the desired product which contains 9.o% sul~ur.
~i' , ' ' ~ "'' .
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lo To a mixture Or 100 parts of soybean oil and 50 ; parts of 1 hexadecene at 165C. J under nitrogenS is added ~ o~er 20 minutes, with stirring, 20.6 parts o~ sul~ur. An J exothermic reaction occurs which causes the temperature to i rise to 200C. It is he&ted at 175-200C. ~or 6 hours, jl 15 cooled to llOi~C. and filtered to yield the desired product , ' ' , ' .
~ which contains ll.li~ sulfur.
,. : -Example ~i mixture of 100 parts of soybean oil and 50 . . .
parts of commercial Cl6 ~-olefins is heated to 175C.
20~ under nitrogen and 17.4 parts of sul~ur is added gradually, 1. , . : .
~ ~ whereupon an exothermic reaction causes the temperature to . . . .
~ ; rise to 205C. The mixture is heated at 188-200C for 3~ five hours, allowed to cool gradually to 90C. and filtered ~ to yield the desired product containing 10.13i~ sulfur.

¦~ 25 Example 4 ~ Following the procedure of Example 3, a sulfurized ', . .
product is prepared from 100 par~s of soy~ean ail, 50 parts of commercial Cl5-l8 ~-olefins and 17.4 parts of sulfur.
It contains 10.1~ sulfur.
, .
. ~, .

_5_ ^

Exa~
Follo~ling the procedure of Example ~, a product containing 10.~3~ sulfur is obtained by the reac~ion of lO0 .
par~s of soybean oil, 50 parts of commercial C 15-20 a-olefins and 17.9 parts of sulfur.

Exarnple 6 ~:
, Following the procedure of Example 3, a product ; containing 9.69~ sulfur is obtained ~rom lO0 parts of soy~
bean oil, 100 parts of cornmercial C22 -28 ~-ole~ins and 23.2 :
parts of sulfur.

~Example 7 .
Following the procedure of Example 3, a produc~
containing 10,16% sulfur is obtained from 100 parts of ~ cottonseed oil, 33.3 parts of commercial Cl5-20 a-olefins ;1 15 and 15. 6 parts of sulfur,-i ~. .
Following the procedure of Example 3, a product ~i containing 8.81~ sulfur is obtained from lO0 parts of a triglyceride having an iodine number of 85-95, 25 parts of 2n co~ erclal C15-18 ~-olefins and 14.5 parts of sulfur, A mixture of 100 parts of soybean oil, 50 parts -~
of commercial C15-18 a-olefins, 1.17 part of triphenyl phos phite and 17.4 parts of sulfur is heated for 16 hours at 145-165C~ under nitrogen~ It is then cooled to room temperature, reheated to 100C. and filtered ~ith the addition of a filter aid rnaterial. The filtered product - -contains 10,13~ sulfur.
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;;ZZ6 J~xamr~ Lo _.
1~ miY~l;ure of :100 parts of soybean oil, ~. 7 par~;s of tall oil acid and 45.3 par~s of commerc~al ~15-18 ~-olefins is heated to ]65~C. under nitrogen, and 17~4 parts of suli`ur is added. The terr,pera~iure of the mixture rises to 191C. It is maintained at 165~200C ~or 7 hours and is then cooled to 90C. and filtered. The product con~ains 10. 13% sulfur.

E xample 11 Following the procedure of Example lOg a product containing 10. ~9~ sulfur is obtained from 100 parts of soy-bean oil, 4 parts of tall oil acid, 46.3 parts of comrr.ercial C 15 -l8 ~ -ole~ins and 20. 6 parts of sulfur Exarl~p le 12 .
Following the procedure of Example 10, a product containing 10. 6% sulfur is obtairied from 100 parts of soy-bean oil, 5.25 parts of tall oil acid, ~4.8 parts OI
commercial Cls-l8 c~-olefins and 17. 4 parts o~ sulfur.

~Example_1~
- 20 Following the procedure of Example 10, a product containing 10.~% sulfur is obtained from 100 par-ts of peanut oil, 5O 25 parts of tall oil acid, 45 parts of comrQercia C 15 -18 t~ -olefins and 170 5 parts of sulfur.

Example 14 Following the procedure o~ 13xample 10, a product containing 12. 41~ sulfur is obtained frorn 100 parts of soybean oil, 5O35 parts of tall oii acid, L16.3 parts of cornrnercial Cl5-la c~-olefins and 26.8 parts o~ suliur.

2~`~

~,xc~t~ 15 Following the procedure o~ Example 10, a product ~.
contairling 9.98$ sul~ur is obtained ~rom 100 parts of scy-~ bean oil, 4.11 parts of tall oil acid~ ~408 par-~s o~ a :~ 5 mixture of C12-16 fractions from ~he polymerization of iso~
butene, and 20.o parts of sul~ur.
- :
E ~
A product containing 1~.7~ sulfur is obtained ~rorn ~, .
100 parts of soybean oil, 5.~ parts of ~all oil acid, 46.2 . ;
; 10 parts of commercial C15~18 ~-olefins, 1 5 parts of triphenyl . phosphite and 2~ parts o~ sul~ur ~ollowing the procedure o~
Example 10 except that a temperature range of 135 165C. is . employed, , . . .
~ Example 17 .i : 15 Following the procedure of Example 10, a product :1 containing 9.54~ sulrur is obtained from 100 parts of soybean . oi], 5.53 parts of tall oil acid, 50.2 parts o~ comrlercial 15 -18 ~ -olefins, ~.18 parts of lecithin and 180 4 parts of ., .
~ : . . sulfur..
',1 ,i .
l: 20 ~ . . , :~:
A product is prepared from 100 parts o~ soybean . oi], 5.4 par~s o* tal1 oil acid, 46.3 parts of col~ercial - :.
. C 15 -18 a-ole~in and 2~.8 parts of sulfur, following the i , .
procedure of ~xample 10 except that the temperature is 155~203C and the product is filtered at 110C. It .
~ contains 14.45~ sulfurO
t. "' Exarnple 19 . A product containing 13,5~ sulfur is prepared : .-J ' ,r~ -r~ ' ~ ~, according -to the method o~` ~xample 18. To 25~ parts of th:is product is added ~8,~ par~s of lard oil. The resulting composi~ion, which has il~lproved solubili~y ~n bright stocks, contains 10~ sulfur.
The composi.tions Or this invention can be employed in a variety of lubri.cating composi.t,ions based on diverse oils o~ lubricating viscosity, including naturàl and syn-thetic lubricating oils and mixtures thereof. The lubrica-ting compositions contemplated include p~incipally crank-case lubricating oils ~or spark-ignited and compression-igni~ed internal combustion engines including automobile and truck engines, two-cycle engine lubr:icants, aviation piston engines, marine and railroad diesel engines~ and the li~e. However, automatic transmission ~luids, trans-axle lubricants, gear lubricants, metal-working lubricants, hydraulic fluids~ and other lubricating oil and grease :i .
compositions can benefit rrom ~he incorpora~ion of the present ~Y~bf~
Natural oils include animal oils and vegetable Z 20 oils (e.gO, castor oil, lard oil) as well as solvent-re~ined or acid-re~ined mineral lubricating oils o~ the paraf~inic, naphthenic, or mixed paraf~inic-naphthenic types. Oils of ` lubricating viscosity derived fro~n coal or shale are also use~ul base oils. Synthetic lubricating oils include hydro-carbon oils and halo~substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, - polypropylenes, propylene-isobutylene copolymers, chlorinated polybu~ylene.s~ etc,); alkylbenzenes (e~g., dodecylbenzenes, tetradecylbenzenes,dinonylbenzenes, di-(2-ethylhexyl) benzenes, etc.); polyphenyls (e.g., biphenyls, terphenyls, , _9_ _ .
,. - . ~ .. .
.. . . ~ , .

~tc.); and the like. ~lkylerle oxide po]y~ers and :Lnter-polymers and derivatives ther~o~ where the terminal hydroxyl groups have been rnodi~i.ed by est~ ication, etherif`ication, etc., constitute another class Or known synthetic ]ubrica~ing oils. These are exemplified by ~he oils prepared through polymerization of ethylene oxide or propylene oxide, the alkyl and aryl ethers of these polyoxyalkylene polymers (e.g., methylpolyisopropylene glycol ether having an average - rnolecular ~eight of lO00, diphenyl ether of polyethylene glycol having a molecular weight of 500-lO00, diethyl ether o~ polypropylene glycol having a molecular weight of 1000-1500, etc.) or mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C3-C8 fatty acid esters, or the C130xo acid diester of tetraethylene glycol.
Another suitable class o~ synthetic lubricating oi]s comprises the esters of dicarboxylic acids (e~g., phthalic acid, succinic acid, maleic acid~ azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid ! ~ dimer, etc~) with a variety of alcohols (e.g., butyl 3 20 alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl , alcohol, pentaerythritol, etc.). Specific exarnples of t these eeters~include dibutyl adipate, di(2-ethylhexyl) sebacate, di-n~hexyl fumarate, dioctyl sebacate, diisooctyl azelateS diisodecyl azelate~ dioctyl phthala~e, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester o~
.~ . .. . .
linoleic acid dimer, ~he complex ester formed by reacting one mole of sebacic acid with t~lo moles of tetraethylene ~3 glycol and t~o mol~s of 2-ethylhexanoic acid, and the like.
Silicon-based oils such as ~he polyalkyl-, polyaryl~
~0 polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils . 1 ' ' ~ I
-10~

comE)rise anoth~r us~ru:L class o:~ synl;hel;ic lubricants ~e.g., tetraet~ly~. si~.icate, tetrai.soprcpyl sili.cate~ tetra~(2-~thylhexyl) si.licake, tetra~ -me~hyl~2-tetraethyl) silica~e~
tetra-(p-tert-butylpheny~) silica~e, hexyl-(4~methyl-2-pentoxy)-disiloxane, poly(methyl~-siloxanes~ poly(methyl~
; phenyl~si].oxanes~ etc.). Other synthetic lubricating oils include liquid esters o~ phosphorus-containing acids (e.gO, tricresyl phosphate, trioctyl phosphate, diethyl ester o~
decane phosphonic acid, etc~), polymeric tetrahydro~urans, 10 and the like, : In general, about 0.05-2~.0 parts (by weight) of the composition o~ this invention is dissolved in 100 parts of oil to produce a satisfactory lubricant. The invention also contemplates the use of other additives in combination 15 with the products o~ this invention. Such additives include, for example, detergents and dispersants o~ the ash~conta:ining or ashless type, oxidation inhibiting agents, pour point depress mg ag~nts, auxiliary extreme pressure agents, color . stabillzers and anti-~oam agents.
- The ash-containing detergents are exernplified by j oil~soluble neutral and basic sal~s of alkali or alkaline~
eaxth metal~ with sulfonic acids, carboxylic acids, or `$;~ organic phosphorus acids characterized by at least one :
,~ ~ direct carbon-to-phosphorus linkage such as those prepared :
` ; 25~ b~ the treatment of an olefi.n polymer (e.g~, polyisobutene -jA'I' ` having a ~nolecular weight o~ 1000) wi~h a phosphorizing agent such as phosphorus trichloride, phosphorus heptasul-~ide, phosphorus pentasulfide, phosphorus trichloride and sulfur, ~Ihite phosphorus and a sulfur halide, or phosphoro~
~ thioic chloride. The most cortL~only used salts of such acids ~
~, . .
,.

. ~, ' - .
,. ' ' .

`
~r~ oSe Or sod1um, po~ssium, li~hium, calcium~ m~gneslum, strontiuln and barium.
The tcrm "b~sic salt" is used to designate metal salts wherein the metal is present in stoi.chiometrlcally larger amounts than the organic acid radical. The cor~nonly employed methods for preparing the basic salts involve hea~ing a mineral oil solution of an acid with a stoichio- !
metric excess of a metal neutralizing agent such as the metal oxide3 hydroxide, carbonate, bicarbonate, or sulfide at a -temperature above 50C. and filtering the resulting mass.
The use of a "promoter" in the neutralization step to aid the incorporation of a large excess o~ metal likewise is known. Examples o~ compounds use~ul as the promoter include phenolic substances such as phenol, naphthol, alkylphenol, 'l thiophenol, sulfurized alkylphenol, and condensation products ~ -o~ ~ormaldehyde with a phenolic substance; alcohols such as methanol, 2-propanol, octyl alcohol, cellosalve, carbitol, ethylene glycol, stearyl alcohol, and cyclohexyl alcohol;
and amines such as aniline, phenylenediamine, phenothiazine, phenyl-~-naphthylamine, and dodecylamine. A particularly e~ective method ~or preparing the basic salts comprises mi~ing an acid with an excess o~ a basic alkaline earth , .. . . ~ .
metal neutralizing agent, a phenolic promoter compound, and ~ -a small amount o~ water and carbonating the mixture at an ` ~-?5 elevated temperature such as 60-200C.
AshIess detergents and dispersants are illustrated `~ ~
by the interpolymers o~ an oil-solubilizing monomer, e.g.~ ~`
decyl methacrylate, vinyl decyl ether, or high molecular weight olefin, with a monomer containing polar substituents, e.g., aminoalkyl acrylate or poly-(oxye~hylene)-substitU~ed ' : ''~ ' ' , ,~ ~

.. . . .. .. .. .. . ... .. .

J/~
~cryla~e; ~he a~lirle S~l~S, ~mid~s, an~ im~ s of' oi].-solubl~ monocarboxylic or dica.rbo~ylic acids such as s~earic acid, oleic acid, tall oil acid, and high molecula~ wei~ht ~ .
- alkyl or alkenyl-substituted SUCCi.lliC acid, ~specially us~ful as ashless detergents are the acylated polyamines and similar nitrogen compounds containing at least about 54 carbon atoms as described in U.S. patent 3,272,71l6; reaction products of such compounds with other reagents i~cluding boron compounds, phosphorus compounds, epoxides, aldeh~des, lO organic acids and the like; and esters of hydroc3rbon~
substituted succinic acids as described in U.S. patent 81,022.
Auxiliary extreme pressure agents and cor.rosion-~, inhibiting and oxidation-inhibiting a~ents are exemplified by chlorinated aliphatic hydrocarbons such as chlorinated ,~ wax; .organic sulfides and polysul~ides such as benzyl disul~ide~. bis(chlorobenzyl) disulfide, dibutyl tetrasul~ide~
sul~urized methyl ester o~ oleic acid, sulfurized alkyl- :
. phenol, sul~urlzed dipentene) and sulfurized terpene;
: 20 phosphosulfurized hydrocarbons such as ~he reaction product o~ a phosphorus sul~ide with turpentine or methyl oleate;
I phosphorus esters including principally dihydrocarbon and ` :
trih~drocarbon phosphites such as dibutyl phosphite~
diheptyl phosphite, dicyclohexyl phosphite, pentyl phenyl 25 ~ phosphite,: dipentyl phenyl phosphite, tridecyl phosphite~
~ ~ distearyl phosphite, dimethyl ~aphthyl phosphite, oleyl .
~ ~ 4-pentylphenyl phosphite, polypropylene (molecular weight 500)-substituted phenyl phosphite, diisobutyl-substituted phenyl phosphite; metal thiocarbarnates~ such as ~inc dioctyldithiocarbamatc~ and bariurn heptylphenyl dithio- :.
- ~' .~ ~
, . ,. ~' -13 .

.. ... .
"
.... ... .... ,, . . . .

~ ~ .
carbamat~; Group II m~l;al phosphorodithi o~e~ ~uch as zinc dicyclohexylphosphorod.ithio~te~ zinc dioctylp~?osphoro~
dithioa~e~ bar.ium di(hept~lphenyl) phosphorodithioate, .~ cadmiurn dinonylphosphorodithioate, and the zinc salt of a .` 5 phosphorodithioic acid produced by the reaction o~ phosphorus .. . .
1 pentasulfide with an equimolar mixtUre of isopropy] alcohol :, . . . ~~ ~nd n-hexyl alcohol.
.; It is possible to form the lubrican~s o~ this ,...................... . .
'2 invention by dissolving the various additives, or oil ,.. .
solutions thereof~ directly in a mineral oil. ~iIo~ever, .' . it is generall~ more convenient and is pre~erred to prepare additive concentrates containing two or more Or the desired -~
~ .
additives, and to dissolve these concentrates in the mirleral oil to rorm the ~inal lubricating composition~
Typical lubricating compositions according to this .
.,, , ~,. :~ invention are listed în Tables I~III. All amounts listed,.
except those ~or mineral oil, are exclusive of oil present i;; as~diluen~
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In tne lubI:icating composi(;ions l:lsl;ed abo~re, the su:l.furi7.ed co~positions of this inventlon provicle the ~,roperi;ies previously im.pa:rted by slllI'urized sperm oil.

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Claims (18)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. A method for preparing a sulfurized composition of matter which comprises reacting, at about 100-250°C., sulfur with a mixture comprising (A) 100 parts by weight of at least one fatty acid ester, (B) 2 to 50 parts by weight of at least one fatty acid, and (c) about 25-400 parts by weight of at least one aliphatic olefin containing about 8-36 carbon atoms.

2. A method according to claim 1 wherein reagent A is at least one fatty oil.

3. A method according to claim 1 wherein reagent C is at least one .alpha.-olefin.

4. A method according to claim 1 wherein reagent C is at least one C12-20 .alpha.-olefin.

5. A method according to claim 4 wherein reagent B is tall oil acid and is present in the amount of about 2-8 parts by weight.

6. A method according to claim 4 wherein reagent A is soybean oil.

7. A method according to claim 6 wherein reagent B is tall oil acid and is present in the amount of about 2-8 parts by weight.

8. A method according to claim 7 wherein reagent C is present in the amount of about 25-75 parts by weight.

9. A sulfurized composition of matter prepared by the method of claim 1.

10. A sulfurized composition of matter prepared by the method of claim 4.

11. A sulfurized composition of matter prepared by the method of claim 6.

12. A sulfurized composition of matter prepared by the method of claim 7.

13. A sulfurized composition of matter prepared by the method of claim 8.

14. A lubricating composition comprising a major amount of a lubricating oil and a minor amount of a composition according to claim 9.

15. A lubricating composition comprising a major amount of a lubricating oil and a minor amount of a composition according to claim 10.

16. A lubricating composition comprising a major amount of a lubricating oil and a minor amount of a composition according to claim 11.

17. A lubricating composition comprising a major amount of a lubricating oil and a minor amount oil a composition according to claim 12.

18. A lubricating composition comprising a major amount of a lubricating oil and a minor amount of a composition according to claim 13.