United States Patent (19) 11) Patent Number: 4,873,008

Landis et al. 45) Date of Patent: Oct. 10, 1989

54) JOJOBA OIL AND JOJOBA OIL FOREIGN PATENT DOCUMENTS
DERVATIVE LUBRICANT COMPOSTIONS
3327127 7/1984 Fed. Rep. of Germany .
75 Inventors: Phillip S. Landis, Alexandria, Va.; OTHER PUBLICATIONS
Frank Erickson, Seattle, Wash.
Estefan, “Jojoba as a Possible Lubricant', American Oil
(73) Assignee: International Lubricants, Inc., Chemists Society Meeting Presentation, (1983).
Seattle, Wash. Miwa et al., "Extreme Pressure Lubricant Tests on
Jojoba and Sperm Whale Oils,” J. Am. Oil Chemists
(21) Appl. No.: 273,709 Soc., 56:76570, (1979).
Gisser et al., "Jojoba Oil as a Sperm Oil Substitute',
22 Fied: Nov. 16, 1988 Wear,34:53-63, (1975).
Wolff, “Seed Lipids,” Science, 154:1140-49, (1966).
Schwab et al., "Configuration of Octadery Tetrasul
Related U.S. Application Data fide,” Phosphorus and Sulfur, 10:123-26, (1981),
63 Continuation of Ser. No. 88,186, Aug. 21, 1987, aban Schawb et al., I.
doned. Princen et al., “Development of New Crops for Indus
trial Raw Materials,” JAOCS, 61:281-89, (1984).
51 Int. Cl."........................................... C10M 141/10 Schwab et al., “Hydrogen Sulfide Adducts of Methyl
52 U.S. Cl. .................................. 252/46.6; 252/49.8; trans, trans-9,11-Octacecadienoate,' J. Ann. Oil Chem
252/56 R ists' Soc., 55:860–64, (1978), Schwab et al. III.
58 Field of Search .................... 252/46.6, 49.8, 56 R Schwab et al., “Nucleophillic Addition of Hydrogen
Sulfide to Methyl Oleate, Methyl Linoleate, and Soy
56) References Cited bean Oil, J. Ann. Oil Chemists' Soc., 52:236-239, (1975),
U.S. PATENT DOCUMENTS Schwab et al. II.
Kammann et al., “Sulfurized Vegetable Oil Products as
2,298,855 10/1942 Wright .............................. 252/56 R Lubricant Additives,” JAOCS, 62: (1985).
2,450,403 9/1948 Wells .................... ... 252/48.6
2,628,187 2/1953 Frohmader et al. .................. 167/82 Primary Examiner-William R. Dixon, Jr.
2,921,874 / 1960 Kubie ................... ... 143/6.14 Assistant Examiner-Jerry D. Johnson
3,729,415 4/1973 Davis et al. ........................... 252/25 Attorney, Agent, or Firm-Seed and Berry
3,763,244 10/1973 Shubkin ... ... 260/676 R. 57 ABSTRACT
3,780,128 12/1973 Shubkin............................ 260/683.9
3,849,323 11/1974 Hollinshead .......................... 252/56 There is disclosed an improved lubricant base composi
3,850,828 11/1974 Dodson et al. ....................... 252/59 tion for incorporation into a wide variety of lubricating
3,873,457 3/1975 Magne et al. ... ... 252/47.5 compositions. The improved lubricant base composi
4,329,298 5/1982 Brown et al. .... . 260/405.6 tion comprises at least two ingredients selected from
4,360,387 11/1982 Brown et al. ........ ... 106/243 jojoba oil, sulfurized jojoba oil, and a phosphite adduct
4,420,647 12/1983 Hammond et al. ................... 585/10
4,557,841 12/1985 Arndt ................... ... 252/32.7 of jojoba oil.
4,582,617 4/1986 Doner et all 252/52 A.
4,587,107 5/1986 Wisniak .............................. 252/48.6 12 Claims, No Drawings
 4,873,008
1. 2
art. There remains, however, much room for improve
JOJOBA OLAND JOJOBA OLDERVATIVE ment of lubricating properties for automotive and ma
LUBRICANT COMPOSITIONS rine oils, cutting fluids, precoat oils, metal-working oils,
ATFs, gear oils, and way lubricants. The present inven
This application is a continuation of U.S. patent appli 5 tion represents novel compositions which are superior
cation Ser. No. 088,186, filed Aug. 21, 1987, now aban to prior art lubricants for use in many well-known appli
doned under C.F.R.S 1.62. cations.
DESCRIPTION DISCLOSURE OF THE INVENTION
1. Technical Field O The present invention provides a lubricant base and
The present invention relates to a lubricant base com lubricating compositions containing a mixture of at least
position and lubricant compositions with antifriction two of the following three compounds, jojoba oil, sulfu
properties that contain jojoba oil and jojoba oil deriva rized jojoba oil, and a phosphite adduct of jojoba oil.
tives as the active lubricating agents. More specifically, The compositions of the present invention provide su
this invention relates to a composition of jojoba oil and 15 perior lubricating characteristics, having antifriction
a phosphite adduct of jojoba oil and/or a sulfurized characteristics and antiwear and load-carrying proper
jojoba oil that is used in combination to form the active ties that are superior to any one compound alone. Im
lubricating agents. proved antifriction characteristics may result in re
2. Background Art duced fuel consumption for internal-combustion en
Jojoba oil is a natural mixture of straight-chain, unsat 20 gines and lowered operating temperatures when used in
urated, monocarboxylic acid esters comprising primar engines and other industrial machinery. Further, the
ily C18 to C24 monounsaturated alcohols esterified with present invention provides for cutting fluids, precoat
C18 to C24 monounsaturated acids. The double bond is oils, metal-working oils, ATFs, gear oils, way lubri
located predominantly in the C9 position in both the cants, greases, aviation oils, textile lubricants, hydraulic
alcohol and acid portion of the esters. Jojoba oil is con 25 oils, circulating oils, steam cylinder oils, spindle oils,
ventionally cold-pressed from the seed of Simmondsia fire-resistant fluids, and automotive and marine oils that
chinensis, a desert shrub native to California, Arizona, incorporate the inventive lubricant base as the active
and Mexico. lubricating agent.
Jojoba oil and many of its derivatives have been dis BEST MODE FOR CARRYING OUT THE
closed in the literature. Jojoba oil has been used primar 30
INVENTION
ily in cosmetics and hair shampoos, but has also been
disclosed as useful as a lubricant. Arndt, U.S. Pat. No. As noted above, the present invention comprises a
4,557,841, refers to jojoba oil as a lubricating additive lubricant base and a lubricating composition with anti
and useful in the range of 0.1% to 10% (w/w) in a friction properties, including antiwear and load-carry
motor oil with a standard motor oil formulation. Kuble, 35 ing properties, consisting of a lubricant base and a base
U.S. Pat. No. 2,921,874, refers to the use of jojoba oil as fluid. The lubricant base comprises a mixture of two or
a cold forming lubricant for use in cold extrusion of three of the ingredients selected from the group consist
metals. Further, Brown et al., U.S. Pat. No. 4,360,387, ing of jojoba oil, a phosphite adduct of jojoba oil, and
refer to the use of isomorphous compositions of trans sulfurizedjojoba oil. The amounts of ingredients used in
isomerates of jojoba oil as useful as food machinery the compositions of this invention are based upon the
lubricants. Hollinshead, U.S. Pat. No. 3,849,323, refers final lubricating composition. The lubricating base can
to blended petroleum products for lubrication contain comprise about 0.1% to about 20% (w/w) jojoba oil
ing a natural oil, such as jojoba oil. and about 0.1% to about 5% (w/w) sulfurized jojoba
There is a largely unfulfilled need for new and im oil. Alternatively, the lubricant base can comprise about
proved lubricants and lubricant additive systems to 45 0.1% to about 20% (w/w) jojoba oil, about 0.1% to
improve the friction properties of lubricants, such as about 5% (w/w) sulfurized jojoba oil, and about 0.1%
cutting fluids, precoat oils, metal-working oils, auto to about 5% (w/w) of a phosphite adduct of jojoba oil.
matic transmission fluids (ATFs), gear oils, way oils, Another lubricant base combination can comprise about
and automotive and marine oils. Various jojoba oil de 0.1% to about 20% (w/w) jojoba oil and about 0.1% to
rivatives alone have been suggested as lubricating oil. 50 about 5% (w/w) of a phosphite adduct of jojoba oil.
compositions. For exampler, German Pat. No. The lubricant base must contain a mixture of at least
3,309,211 refers to the reaction ofjojoba oil with P2S5 at two of the three ingredients selected from the group
high temperature and under a nitrogen atmosphere. consisting ofjojoba oil, a phosphite adduct ofjojoba oil,
German Pat. No. 3,327,127 refers to the use ofjojoba oil and a sulfurized jojoba oil, and possibly all three of
in a sulfochlorinated mixture to improve anticorrosion 55 these ingredients.
or antiwear properties. Miwa et al. (“Extreme-Pressure The lubricant base is mixed with a base fluid to make
Lubricant Tests on Jojoba and Sperm Whale Oils,” J. a lubricating composition with antifriction properties,
Amer. Oil Chemists' Soc. 56: 765-70, 1979) refers to including antiwear and load-carrying properties. Exam
lubricant tests on sulfurized jojoba oil as an extreme ples of lubricating compositions include cutting fluids,
pressure additive for motor oils, gear lubricants, and precoat oils, metal-working oils, ATFs, gear oils, way
automotive transmission fluids. Miwa et al. found that lubricants, greases, aviation oils, textile lubricants, hy
the sulfurized jojoba oil as an antiwear additive for draulic oils, circulating oils, steam cylinder oils, spindle
lubricants was at least equivalent to, and in some cases oils, fire-resistant fluids, and automotive and marine
superior to, sulfurized sperm oil. oils. Examples of base fluids include hydrocarbon oil;
The use of jojoba oil as a lubricating derivative or 65 synthetic hydrocarbon; an ester-based lubricant; a min
agent in the prior art has been confined to single-agent eral oil; a mixture of a mineral oil and an ester-based
use, i.e., jojoba oil and sulfurized derivatives of jojoba lubricant; a mixture of mineral oil, synthetic hydrocar
oil have been used individually as single agents in the bon, and an ester-based lubricant; a mineral oil-based
 3
4,873,O08
4.
grease; and a synthetic hydrocarbon-based grease. Spe wherein R is as defined as above, di-2-ethylhexyladi
cifically, the base fluids are: pate, di-2-ethylhexylsebacate, didecyladipate, and dide
a mineral oils, such as paraffinic neutral 100", furfu cylsebacate;
ral-refined paraffinic oil, solvent-refined napthenic oil, d. dialkylbenzenes, such as didocecylbenzene;
and solvent-refined aromatic oil; e. polyglycols, such as UCON fluids, poly
b. synthetic hydrocarbon oils, such as hydrogenated propyleneglycols of 1000 to 3000 molecular weight and
or partially hydrogenated polydecene and other olefins, polyethyleneglycols of 1000 to 3000 molecular weight;
hydrogenated hexene oligomer, hydrogenated octene f. alkylaromatics; and
oligomer, hydrogenated decene oligomer, hydroge g. dicarboxylic acids.
nated C6-10 oligomer, and hydrogenated C8-10 oligomer; 10 Jojoba oil has the following structural formula:
c. ester fluids, such as pentaerythritol esters having
the structures:

O
CHCH2CH=CHCH-i-o-CH2CH=CHCH2CH,
O
15
(Hi-o-c-ch wherein
j=7, 9, 11 or 13
cho-c-o-CH-i-CH-O--ch, O k= 6, 8, 10 or 12
CH2-O-C-C4H9 While other sulfurized jojoba oils may be used in the
O
20 present invention, a preferred sulfurized jojoba oil is the
product of a reaction of jojoba oil and 10% to 20%
and sulfur to yield the following:
A-S-A and
Hi-o-c-R 25
R-c-o-ch--CH-O--R
O
CH-O--R
O 30
and mixtures of both wherein A refers to the struc
wherein R is C4H9, C6H13, C8H17, or mixtures thereof, ture of jojoba oil.
esters of trimethylolpropane and dipentaerythritol of While other phosphite adducts of jojoba oil may be
the structures: used in the present invention, a preferred phosphite
35 adduct of jojoba oil is formed by the reaction of jojoba
oil and a compound of the formula:
th-0--R
,
CH-i-CH-O--R
O 40
CH2-O-C-R
O
wherein R = H, C1-12 alkyl, C1-12 aryl, C1-12 alkaryl,
C1-12 aralkyl, and cyclo C-12 alkyl. Preferably, R = C4-8
and alkyl, C4-8 alkaryl, C4-8 aralkyl, and cyclo C4-8 alkyl.
45 Most preferably, R is n-butyl.
O O As may be seen from its structural formula, jojoba oil
has two carbon-carbon double bonds. Accordingly, the
sh-o-c-R sh-o-c-R
R-C-O-CH2-C-CH2-O-CH-C-CH2-o-c-R
phosphite adduct can be a diadduct or a monoadduct of
the jojoba oil. There are thus four examples of the phos
O
I O 50 phite adduct ofjojoba oil are when R is butyl as follows:
CH2-O-C-R CH-O--R
O

CHCH)H-CHCH)--O-(CH2CH-H-CH2CH,
(-CHO:O O Ro-nich):
O

CHCHCHH-CH)-i-o-Chogh-chschich,
(a cho). O O P(O-n-C4H9)2
O
 4,873,008
5
-continued
CHCHH-CHCH)--O-(CH2CH=CHCHCH
O

CHCH2CH-HCH)--O-(CH2CH=CHCH-CH
O

whereinj and k are defined as above.

The present invention is further illustrated by the between two stationary V blocks. The pin as well as the
following examples which following examples are of V blocks can be made of various materials. The temper
fered as an illustration and not a limitation of the present 15 ature of the lubricant bath into which the pin and V
invention. block are placed may also be varied. The load is applied
Examples of the lubricant base and lubricating com by a ratchet arrangement. Wear measurements made
positions are provided in the Tables 1 and 2. The at above the transition pressure, that is, the load at which
tached tables also provide performance results from the lubricant film breaks down, can be a useful parame
standard tests, including low-velocity friction appara 20 ter if carried out under conditions comparable to actual
tus, the 4-ball wear test, and the Falex test. The proce operations.
dures for each test are as follows. The following Tables 1 and 2 illustrate base fluids,
jojoba oil in base fluids, jojoba oil with a dibutyl phos
4-BALL TESTS FOR ASSESSING phite adduct plus base fluid, a jojoba oil plus dibutyl
EXTREME-PRESSURE PROPERTIES 25 phosphite adduct and sulfurized jojoba oil plus base
The measurement of friction as related to rolling, fluid for the LVFA test, the Falex wear test, and the
drawing, and other metal-working operations depends 4-ball wear test. The two tables illustrate the improved
upon the surface of the tool and workpiece and the lubricating properties of the compositions of the present
viscosity and chemical makeup of the lubricant, as well invention.
as the pressure and temperature developed during pro 30 TABLE 1.
cessing. The 4-ball wear test machine provides, under LVFA, 9% Reduction in
controlled testing conditions, a procedure for measur Coefficient of Friction
ing friction. The machine consists of three balls touch Sliding Speed Sliding Speed
ing each other and clamped together in a horizontal Compound Wt. 92 5 ft/min. 5 ft/min.
plane. A fourth ball touches three clamped balls by 35 Base Fluid" 100.0 O O
being positioned between the three and is driven by a Jojoba Oil 2.0 2 2
motor so that it revolves in contact with the clamped Base Fluid
Jojoba Oil
98.0
10.0 8 12
balls. The rotation takes place within a reservoir con Base Fluid 90.0
taining a test lubricant. A temperature-measuring de Jojoba Oil 1.0 21 20
vice, as well as a heater, provides a method for control Di-n-butylphosphite
ling the temperature of the test fluid. The rotating ball is Adduct
Base Fluid
40
95.0
loaded and then rotated for a specific time at a specific Jojoba Oil 5.0 24 28
speed. At the conclusion of the test, the scar patterns Di-n-butylphosphite
developed on the balls are measured. Any stains are Adduct 2.0
observed, the diameter of the scar is measured, and the 45 Base Fluid 93.0
Jojoba Oil 5.0 15 19
coefficient of friction is calculated by dividing the tan Di-n-butylphosphite
gential force by the normal force at the ball surface. Adduct 2.0
Sulfurized Jojoba Oil 1.0
LOW-VELOCITY FRICTION APPARATUS Base Fluid 92.0
The low-velocity friction apparatus (LVFA) is used 50 Base Fluid is 100' Paraffinic Neutral Mineral Oil
to measure the friction of test lubricants under various
loads, temperatures, and sliding speeds. The LVFA TABLE 2
consists of a flat steel surface (diameter 1.5 inches) 4-Ball Wear Test
which is attached to a drive shaft and rotated over a Results
stationary, raised, narrow ringed steel surface (area 0.08 55 Wear Scar Weld Falex Test
inch). Both surfaces are submerged in the test lubri Diameter Load Lbs. to Fail
cant. Friction between the steel surfaces is measured as Base Fluid 0.94 20 750
a function of the sliding speed at a lubricant temperature Base Fluid -- 1% Jojoba 0.78 60 -
of 250 F. The friction between the rubbing surfaces is Base Fluid + 5% Jojoba 0.72 80 -
measured using a torque arm/strain gauge system. The Base Fluid - 2%. Jojoba --
5% Sulfurized Jojoba 0.52 240 4500
strain gauge output, which is calibrated to be equal to Base Fluid -- 2%. Jojoba --
the coefficient of friction, is fed to the Y-axis of an X-Y 0.5%. Phosphite Adduct 0.52 220 4500
plotter. The speed signal from the tachometer-genera Base Fluid -- 1% Jojoba --
tor is fed to the X-axis. 2% Sulfurized Jojoba --
65 0.5%. Phosphite Adduct 0.45 280 4900
FALEXTEST
The Falex test consists of a method for measuring the The lubricant base may be added to different base
torque and friction developed during rotation of a pin fluids to obtain a composition having a variety of end
 7 4,873,008 8
use applications. Examples of end-use applications with adduct on the jojoba oil moiety is at a carbon-carbon
different base fluids are listed in Table 3. double bond.
TABLE 3 5. The lubricant base concentrate according to claim
Viscosity 1 wherein the sulfurized jojoba oil is selected from the
Application Base Fluid SUS G 100' F. 5 group consisting of:
Auto Engine Oil Mineral Oil and/or Ester
Fluid and/or Synthetic
Hydrocarbon Oils 100-200
Metal-Working Mineral Oils
Lubricant 100-200 10
Gear Lubricant Mineral Oils 300-3000
Textile Lubricant Polyethyleneglycols
Polypropyleneglycols and combinations of both, wherein x is 1 to 3 and A is
Aviation Oils Pentaerythritol Esters and jojoba oil.
Trimethylolpropane Esters 100-150
Grease Mineral Oil
15
6. A lubricating composition with antifriction proper
Synthetic Hydrocarbons 1000-2000 ties comprising a base fluid and a lubricant base concen
Hydraulic Oils Mineral Oils trate comprising a mixture of about 0.1% to about 20%
Synthetic Hydrocarbons 00-300
Circulating Oils Mineral Oils (w/w) jojoba oil, about 0.1% to about 5% (w/w) of a
Synthetic Hydrocarbons 900-3000 sulfurized jojoba oil, and about 0.1% to about 5%
Gas Engine Oils Mineral Oils
20
(w/w) of a phosphite adduct of jojoba oil.
Synthetic Hydrocarbons 350-600 7. The lubricating composition according to claim 6
Diesel Engine Mineral Oils, Esters and
Oils Synthetic Hydrocarbons 600-1000 wherein the base fluid is selected from the group con
ATFs Mineral Oils sisting of a hydrocarbon oil, a synthetic hydrocarbon
Synthetic Hydrocarbons 140-300 oil, an ester-based lubricant, a mineral oil, a mixture of
Way Lubricants Mineral Oils a mineral oil and an ester-based lubricant, a mixture of
Synthetic Hydrocarbons 150-1000 25
Steam Cylinder Mineral Oils mineral oil, synthetic hydrocarbon oil and ester-based
Oils 1800-1900 lubricant, a mineral oil-based grease, and a synthetic
Fire-Resistant Mineral Oil (Water) hydrocarbon-based grease.
Fluids 400-500 8. The lubricating composition according to claim 6
Spindle Oils Mineral Oils 50-130
30 wherein the phosphite adduct ofjojoba oil is a mono- or
a di-adduct of the reaction product of
The principles, preferred embodiments and modes of
operation of the invention have been described in the O
foregoing specification. The invention which is in
tended to be protected herein, however, is not to be 35
constrained as limited to the particular forms disclosed,
since these are to be regarded as illustrative rather than and jojoba oil, wherein R is selected from the group
restrictive. Variations and changes may be made by consisting of hydrogen, C1-12 alkyl, C1-12 aryl, C1-12
those skilled in this art without departing from the spirit alkaryl, C1-12 aralkyl, and cyclo C1-12 alkyl.
of the invention. 9. The lubricating composition according to claim 8
We claim: wherein R is selected from the group consisting of C4-8
1. A lubricant base concentrate comprising a base oil alkyl, C4-8 alkaryl, C4-8 aralkyl, and cyclo C4-8 alkaryl.
10. The lubricating composition according to claim 9
and a mixture of about 0.1% to about 20% (w/w) jojoba
oil, about 0.1% to about 5% (w/w) of a sulfurized jo wherein R is butyl.
joba oil, and about 0.1% to about 5% (w/w) of a phos 45 11. The lubricating composition according to claim 8
phite adduct of jojoba oil. wherein the point of attachment of the phosphite ad
2. The lubricant base according to claim 1 wherein duct moiety on the jojoba oil moiety is at a carbon-car
the phosphite adduct of jojoba oil is a mono- or a diad bon double bond.
duct of the reaction product of 12. An improved base fluid of the type normally used
as a gasoline engine oil, a pre-coat oil, a gear lubricant,
50 a textile lubricant, an aviation oil, a grease, a hydraulic
O
oil, a circulating oil, a diesel engine oil, an automatic
transmission fluid, a way lubricant, a steam cylinder oil,
a marine oil, a metal-working oil, and a spindle oil,
and jojoba oil, wherein R is selected from the group wherein the improvement comprises:
consisting of hydrogen, C1-12 alkyl, C1-12 aryl, C1-12 55 incorporating a lubricating base concentrate compris
alkaryl, C1-12 aralkyl, and cyclo C1-12 alkyl. ing a mixture of at least three ingredients selected
3. The lubricant base concentrate according to claim from the group consisting of jojoba oil, phosphite
2 wherein R is butyl. adduct of jojoba oil, and a sulfurized jojoba oil into
4. The lubricant base concentrate according to claim said base fluid.
2 wherein the point of attachment of the phosphite 60 k it k is k

65