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- 2,406,575
Patented Aug..27, 1946 ‘ '
umrao srarss PATENT ' oFr-ics _,
' f 2,406,575
I
PREPARATION ormmraovnn
I
.
,
LUBRICANT
I
Harris D. _
David W. Young, Roselle, N. 1.‘,Y.,and
assignors to
Hlneline, Mount Vernon, N.
Standard Oil ‘Development Companyga corp,
poration of Delaware
- No sawing, v
_
I
,
'
'
.
Appllcation‘luly s, 1944,
Serial No. 544,148
' 11 Claims. (crass-46.6)
1
'- mer yields the desired thickening and-the desired.
lubricants '
improvement in viscosity index. I
_
This invention relates to thickened relates
es
Thus the present invention provides a, new com
having an improved viscosity index;
pécially to thickened lubricants of improved vis. : ' position of matter comprising a hydrocarbon solu-
‘I .7 cosity index which have extreme- pressure prop
tion of a cyclicized polymer such aspolymethyl
pentadiene containing combined sulfur, and
smaller or negligible quantities of combined phos?
phorous, dissolved in a hydrocarbon lubricant to
yield a solution which remains liquid at low tem
peratures, and retains its body at relatively high
temperatures. Other objects and details of the
invention will be apparent from the following de- v"
verties; and relates particularly to lubricants con
taining phosphorous pentasul?de treated, cycli
cized polymer such as polymethyl pentadiene.
' A number of oil soluble substances have been
fomid, which serve when dissolved in lubricants
to improve its
'to, thicken thelubricant and also
viscosity index; that is, to reduce the rate of
I ‘change of viscosity with change in temperature of
scription.
-
_
_
,
The raw material for the present invention is
a relatively high molecular weight polyoleilnic
‘polymer which is capable of. cyclicization. The
‘preferred raw material is polymethyl pentadiene;
that is the polymer of 2, methyl 'pentadiene-1,3_v
which polymerizes at low temperature quite r'ead- _
ily into high molecular weight polymers, and when
the lubricant; among the best of which has been
polyisobutylene. Polylsobutylene, however, lacks
extreme pressure lubricating properties, and while
the viscosity index of a lubricating 011 containing '
is excellent, it does not stand up
"polyisobutylene
.well under conditions where lubrication of sur
faces under extremely heavy pressure is required.
On the other hand, various substances have been 20 -_ so polymerized cyclicizes quite readily. After» , '
offered which contain such inorganic radicals as ‘
natively almost any of, the other high molecular
> I sulfur and chlorine
weight polyole?nic polymersare useful. Thus,
which improve the extreme _
_ such polyole?ns as» 2,5-methyl pentadiene-1,3
pressure properties of the'lubricant, but do not
or 2-methyl-5.-ethyl pentadiene-1,3 or the like are
similarly useful. That is, substantially any of
‘improve the viscosity index; and di?i- '
culty is encountered in adding both agents and
obtaining satisfactory results.
"25
>
more than 5 carbon atoms
in which there is an aliphatic sub
" - the polyole?ns having
The present invention provides a single soluble
in a single substance, con;
addition agent which,
tains ‘both V. I. improving elementsand E. P. im
molecule,
I per
stituent
on the second carbon atom with a double
linkage between the ?rst and second carbon atom, v
is useful. Those compounds‘ which are c'onju»
‘ proving elements and is found to yield an excellent
gated, that is, contain two double linkages sepa
viscosity index, and, simultaneously, excellent ex
treme pressure properties.
.I
‘rated by a‘ single linkage, are preferred, but the .
v
condition of conjugation is not‘ necessary.. The
For this purpose a polymerizable polyoleiin such
limiting molecular size of the compounds is‘still _.
" ,as 2-methyl pentadiene 1,3- is polymerized at low
high as 12 or 14
temperatures by the application of a ‘Friedel 35 unknown, but compounds asare
useful. All of '
Crafts catalyst dissolved in a low freezing, non
carbon atoms per molecule
complex forming solvent; to yield a high'molecu- __ » these diole?ns polymerize reasonably vreadily, 1
lar weight polymer: which is, they cyclic-ized by I _-cyc'licize readily, are soluble in hydrocarbons when '
polymerized and cyclicized, and are reactive with
the application of an appropriate cyclicizing agent
such'as p-toluene sulionic acid or aluminum bro
phosphorous Ipentasul?de; Similarly, the triolee
,
the like. ‘The cyclic-.
?ns including such substances as myrcene, hav-l
. mide or'stannic chloride or
ized polymer is then treated at an elevated tem-'
ing the formula
'
A .
_ _
and an
T perature with a compound of phosphorousThe
pre
_' element selected from the sulfur group.
substance is phosphorous pentasul?de
-,;ji_erred
_
I
Alternatively, other analogous com‘ . pounds may be used,‘such for example as P453,
P386, P480 or P2865 or P236 or P488. 01' F286;. This
1
treatment
adds-into the cyclicized polymer (or
. into the oil blend containing the cyclic'lzed poly
mer) a considerable quantity
'
I
(cmnmcncmcme-cmo'm
45
' are very desirable raw materials, since they poly- I
_
I-merize readily, cyclicize readily,‘ are oil-soluble
Y when polymerized and cyclicized, and‘ combine
readily‘ with phosphorous pentasul?de after cy» >
50 cyclicization.
of combined sulfur . >
Similarly, the triole?n known as
alloocymene,having the formula '
I
,
‘ (or selenium or tellurium) and a smaller quantity
of combined phosphorous; which, together yield
very e?ective extreme pressure properties while ‘
the high molecular weight or the cyclicized poly
55
is equally advantageously ‘useful. These ‘sub
2,406,675
3
stances are representative of polyole?ns which
polymerize at temperatures below 0° C. into oil
the active methyl halides and a freezing point
below 0° C. (thereby being ‘flow freezing”).
soluble polymers having molecular weightsabove
-
The catalyst solution may be added to the cold
3000, 4000 or 5000, up to several hundred thou
ole?nic material in anyconvenient manner which
5
will
bring the catalyst solution quickly into inti
100 to 330 or above, which are readily cyclicized to
sand, with iodine numbers ranging from about
mate dispersion in the cold ole?n. A convenient '
reduce the‘ overall unsaturation, yet retain, in
method is to spray the catalyst solution through
the cyclicized condition, su?icient unsaturation to
a nebulizer on to the surface of the rapidly stirred
he reactive with phosphorous pentasul?de; and
when so reacted, combine with the phosphorous 10 cold ole?nic material. Alternatively, the catalyst
solution may be jetted into a zone of high turbu-_
and sulfur in such a way that the solubility in
lence in the cold voleiinic material such as the
hydrocarbons remains‘ good, the inorganic atoms
region near to a. rapidly rotating propeller stirrer.
Many other means for adding the catalyst are,
are solidly held so that the compound is stable,
yet the inorganic molecules are so placed as to re
sult in an effective extreme pressure improvement.
however, available.
Of these compounds, the polymer of methyl 15 The reaction'proceeds rapidly to yield the de- I
pentadiene is preferred.
siredpolymer, and the conversion may be carried
to a yield of from 40-50% of the amount of
In preparing this polymer, methyl pentadiene'
' of good purity is used. In the examples herein-4‘ , methylpentadiene present, to a yield as high as
after given, a methyl pentadiene having a boiling _ 90-95%. Such high yields are, however, less de
point of 75° C. to 77° C. (at 760 mm. of Hg), 9. 20 sirable since the range of molecular weight is
greater. When the reaction has reached the de
density of 0.7113 and an index of refraction ND”
sired stage, the catalyst supply is interrupted.
1.4472 was used. This material has a purity bet
The solid polymer may be recovered in any de
ter than 95 %, and further determinations indi
sired manner; merely byv boiling off residual un
cate that its purity is in fact approximately 98%.
The methyl pentadiene is cooled to a temperature 25 polymerized methylpentadiene; and refrigerate
about between 0° C. and -—l64=° C. (preferably to. . if present, or the reaction mixture may be treated
with warm water or warm alcohol or warm naph~
a temperature between -—40° C.) as set by liquid
propane, and —'103° C. as set. by liquid ethylene.
tha, with or without small quantities of alcohol
'or the like.
‘The methyl pentadiene by itself may be, cooled, ’
by the application of a refrigerating Jacket to the 80
I
v
polymerization reactor. Alternatively the methylv
The resulting polymer may have a molecular
weight almost anywhere between 2000, 3000 or
cooled by an internal rei’rigerant-diluent.v For
this purpose such substances as liquid propane
of catalyst chosen. The preferred molecular
weight is within the
pentadiene may be diluted with such substancesv
_-12,000 and 30,000-100,000, depending upon the
lowness of the polymerization temperature, the
as the lighter hydrocarbons or the alkyl, mono,
or poiyhalides or carbon disulfide or the like. 35 purity oi’ the methylpentadiene, the presence and
purity of diluent-refrigerant, and the character
Alternatively the methyl‘ pentadiene- may be
range between about 5000 ‘
or liquid'ethane or liquid ethylene or even liquid '
and 35,000 to 45,000 since higher ' ‘molecular
methane may be used; or the material may bis-4°
somewhat more easily in
service and lower molecular weights require an
cooled by solid carbon dioxide, or by dissolved
liquid carbon dioxide; under vacuum if lower tem
peratures are desired.
‘
The cold methylpentadiene is then polymerized
. by the application of a Friedel~0rafts catalyst
which preferably is in solution in a low freezing
_ noncomplex forming solvent.
the polymer is dried in any convenient manner
“ an
be conducted. in several ways. A preferred
method is to put the polymer on the double roll
The Friedel-Crafts
catalyst may be substantially any of the sub
stances disclosed
tov room temperature,
and then is ready for the cyclicization, which may
4
by N. 0. Galloway in his article >
on “The F‘riedel-Crafts Synthesis” printed in the 56
Journal of
“Chemical Reviews,” published for the ,
American Chemical $ociety at Baltimore in 1935
in volume XVII, No. 3, the article beginning on
page 327, the list being particularly well shown
on page 375. These Friedel-Crafts active metal
halides may be used as such in single salts, or
Ol
oral metals or several halides or even with alkoxy
substituents. These catalysts may be solid, liquid
rgéim temperature and is ready for the dissolving
or gaseous (boron tri?uoride being gaseous; 60
S
titanium tetrachloride being liquid; most of the
remainder being solids). For solvent, the alkyl~
D.
-
'
.
Alternatively; the polymer may be dissolved in
light naphtha and treated with stannic chloride
at temperatures ranging from 20° C. to 00° C.
for time intervals ranging from 15 minutes to 80
melting points below 0° C. are also useful; as is 65 hours. This treatment also is effective for cycli
carbon disul?de. All of these substances show - cization, and likewise reduces the iodine number
' to approximately 15 to 50.
an adequate solvent capacity for the Friedel
‘Crafts halides, especially aluminum chloride
Other methods which will be obvious to those
which is the preferred catalyst. Alternatively,
skilled in the art may likewise be used for this
and especially where catalyst complexes contain 70 cyclicizs-tion step. The polymer is then ready for .
the phosphorous pentasul?de treatment. .
ing several halides, are used, the lighter hydro
The polymer is then dissolved in from 0.5% to
carbons such as propane, butane, pentane, hex
10% or 15% in the desired hydrocarbon lubri
ane, and the like may be used; the principal re
cant. For the production of a ?uid lubricant, a
quirements being a solubility of at least 0.5% for
75 high grade, well re?ned oil having a viscosity at
mouohalides are preferred such as methyl or ethyl
chloride. Other alkyl mono or peiyhalides having
2,406,575
5
.
.
6
tion of sulfur without cross linkages retains the
oil-solubility and it is of the essence of the pres
ent invention that, broadly, the polymer is cy
clicized and 'sulfurized without the introduction
210° F. of from 30 S. S. U. to '70 S. S. U. may be
used, sufficient polymer being dissolved in the oil
to bring the viscosity and viscosity index to the
Alternatively, if a heavy grease
5 of cross linkage, in order to obtain a compound
is to be made, a much heavier lubricant stock
of high molecular weight which contains sub
addition
agents
may be utilized and the various
stantial quantities of combined sulfur (the effect
be
incorporated;
used to make heavy greases may
of which is aided by the presence of smaller
together with from 1% to 15% or 20% ofthe
quantities of phosphorous) and accordingly, the
.I desired values.
'
polymer.
To this solution there is then added a substan
_ tial quantity of phosphorous pentasul?de, the
amount ranging from 1% to 10% or 15% of the
v10 invention is applicable to>any polymer which
amount of cyclicized polymer. The oil solution
is then heated to temperatures ranging from
‘ 150". C; to 225° C. for from 15 minutes to 150 15
.
can be 'cycliclzed and combined with phosphorous
pen-tasul?de without the formation of su?icient
cross linkages to destroy the solubility in hydro-i
Example 1
carbons. _
Approximately 100 parts of methyl pentadiene
minutes. The solution is then ?ltered to remove
having a purity vof approximately 95% - were
' 'any uncombined phosphorous pe‘ntasul?de, and
cooled to a temperature or approximately
any insoluble reaction products, the material -be~
ing preferably ?ltered while hot because of the ‘ —88° C. by the addition thereto of approximately
more rapid ?ltering ‘rate. In the preparation. of 20 300 parts of liquid ethane. The mixture was
then polymerized by the addition ‘of approxi
greases it is, of course, desirable that the auxili
mately 50 parts of a solution of aluminum chlo
ary components be added after the ?ltration step.
ride in ethyl chloride having a concentration of
The above outlined procedure applies particu
larly to methylpentadiene, and to its polymers,
approximately 2%, the catalyst solution being
' but substantially the same procedure may be 25 sprayed on to the surface of’ the rapidly stirred
applied to a wide range of polymerizable sub
stances, polymers, and high molecular weight
substances in general, it being merely necessary
oleflnic mixture. The polymerization proceeded
quickly to yield a solid polymer having a molec
ular weight of approximately ‘40,000. The poly
‘ merization mixture was. thrown into hot water
that they be capable of cyclicizatlon; when cy
clicized be soluble in hydrocarbons, and when v30 to volatilize residual refrigerant and to separate.
unpolymerized» methyl pentadiene. The yield
cyclicized retain a sui?ciently high iodine num-_
was approximately 80%. rl‘he polymer was then ’
her, and a sufficient amount of unsaturation to
placed on the double roll mill, washed with water
combine with the phosphorous pentasul?de.
until most of the residual traces of catalyst were
Thus, for instance, an interpolymer of isobu
tylene with a polyole?n having more than 5 car 35, removed. and then approximately 3 parts by
weight (per hundred of polymer) of p-toluene.
bon atoms in which a substantial quantity of the
polyole?n is interpolymerized, is similarly useful,
especially with polyolefins up to 12 or 14 carbon
atoms per molecule and especially when the
sulfonic acid were added and ‘thoroughly milled
into the solid polymer. The milling was con
tinued ‘until a thoroughly homogeneous mixture ‘
40 was obtained. The solid mixture was then placed
stantial in amount. That is, it is desirable that _ in a hot air oven- at 100° C. for 30 minutes.
quantity of polyoleiin interpolymerized is sub
The mixture was then cooled and approximate
the iodine number of the cycliclzed polymer be
ly 50 parts by weight of the polymer were dis
above 5, and it is also essential that the cyclicized
solved in 1000 parts by weight of a high grade
' polymer be oil-soluble. This latter requirement
eliminates the polymers oi.’ simple butadiene, iso 45 para?lnic mineral lubricating oil which had a vis
cosity at 210° 1"‘. of 52 S. S. U. and a V. I. of 98.
prene and pentadiene and copolymers containing
.When the solution was complete, yielding a clear
substantial portions of butadiene.
?uid solution, approximately 50 parts by weight
It is further essential that to be useful, the
of powdered yellow phosphoric pentasul?de P285
polymers must cyclicize with a minimum of cross
‘linkages, which is found to be a characteristic of 50 was added, well stirred in and the mixture heated
to a temperature of 180° C. for 30 minutes, the
the polyoleiins having more than 5 carbon atoms,
mixture being well stirred during the heating step.
but not a characteristic of butadiene, and the
At the end of‘ the 30 minutes, the mixture was
presence of butadiene per se to the extent of more
than about 20% introduces so much cross linkage
cooled to approximately 25° C. and filtered
upon cyclicization as to render the cyclicized 55 through a paper ?lter to yield a clear ?ltrate.
Chemical analysis of the clear ?ltrate showed
polymer useless. Thus, copolymers of isobutylene
that it contained 0.58% of phosphorous and 2.03%
with butadiene or isc-prcne or piperylene, con
taining from 2% to 15% or 20% of butadiene are
of sulfur.
v
'
~
Viscosity determinations and viscosity index
butadiene, myrcene, dimethallyl and the like, up 60 determinations showed the following inspection
usable. Copolymers of isobutylene with dimethyl
to 12 or 14 carbon atoms, are usable, especially
results:
when the proportion of interpolymerized diole
?ns‘ exceeds 5% or 10%.
Likewise, as will be
evident from the above description, these poly
ole?ns may be used with any proportion of iso
I butylene, down to 0.
‘ It may be noted that the phosphorous penta- '
chloride treatment of thecyclicized polymer in
,
65
S.B.U.vis;
S.S.U.vls
coslty at ‘100°
cosity at 210°
F.
F.
488
74
V. I.
'
l 131
These results show that the resulting oil has
troduces suli’ur into the molecule withoutthe
establishment of any cross linkage, differing in 70 an excellent viscosity and an excellent viscosity
index.
>
that respect‘ from vulcanization, which intro
Other portions of this oil product were then
duces a maximum of cross linkages into the
charged into the Almen machine for the usual 30
compound between adjacent molecules. It may
second run. At the end of the 30 seconds, the suc
be noted that the introduction of cross linkages
destroys the oil-solubility, whereas the introduc 75 cessive 2 lb. weights were added at 10 second inter
aeoaert
d
vals until the full number or 15 weights had been
added. The oil carried all 15 weights. The pin
and bushing were made of steel-and at the end
of the test the pin and bushing werein good con
dition.
'
ried all 15 weights under this shock loading and
after the test the pin and bushing. which were
made of steel, were in good condition.
The oil was then tested under gradual loading
,
5 conditions in the 'Almen machine as outlined in
Example 1. The cyclicized P255 treated polymer
in solution in the oil carried all 15 weights.
Example 2 ‘Y
.r’l. mixture was prepared consisting of approxi
1 > These results indicate that the oil prepared as
mately 100 parts by volume of methyl pentadiene
above described is a high grade lubricant having a
having a purity of‘ approximately 98% and 400 10 very
advantageous viscosity index and a very val.
parts of liquid ethylene. The presence of the
uable extreme pressure property.
_
liquid ethylene cooled the material to a tempera
While there are above disclosed but a limited
ture of approximately, —l03° C. This mixture
number of embodiments of the invention, it is
was then polymerized by the addition of approxi- ‘
_, a
possible to provide still-other embodiments witlo- 15 out departing from the inventive concept herein
mately '75 parts by volume of a solution or alumi
num chloride in methyl chloride in a concentra
disclosed and it is, therefore, desired that only
such limitations be imposed upon the appended
tion or approximately 0.8%. The polymerization
_ was conducted by spraying the catalyst solution '
claims as are stated therein or required by the
onto the surface oil the rapidly stirred oleilnic ma-‘_ . higher
art.
'
,
terial. The polymerization proceeded rapidly to 20 _ The invention claimed is:
yield a solid polymer having a molecular weight
1. An improved lubricant comprising a hydro~
(by the Staudinger method) of approximately
carbon lubricating agent having dissolved therein
rescue. ‘The polymerization mixture was then
.5 to 20% of polymer of a polyole?n having more
then thrown intowarm Water to volatilize residual
‘ than 5 carbon atoms per‘ molecule which is chartraces of refrigerant and to separate out any un 25 acterized by cyclicization and the presence or
polymerized methyl pentadiene. The yield of ' phosphorous sul?de.
polymer was approximately 69%. The solid poly
' .2. An improved lubricant comprising in com
mer was then placed on a double roll mill and
bination a hyrh'ocarbon material and a solute
washed with water until most of ‘the residual ' therein comprising .5% to 20% of a cyclicized. '
traces of catalyst and monomer were removed. 30 phosphorous pentasul?de treated, polymer of a
When this stage was reached, approximately 10 . polyole?n having 0 to ill carbon atoms per mole
parts by weight (per 100 of polymer) of p-toluene ,
.-cule, a molecular, weight between 3,000 and
sulfonic acid were added and thoroughly milled
100,000 and an. iodine number after cycliclzing
into the solid polymer. The milling was con
between 5 and 50.
'.
tinued until a thoroughly homogeneous mixture 35 3. An improved lubricant‘comprising in com
was obtained. The mixture was then-placed in
bination a hydrocarbon oil and solute therein I
a hot air oven at 100° C.
minutes.w rl‘he ‘
brown polymer mixture was then cooled and ap
comprising .4» to 30% of a cycllcized, phosphorous
pentasulfide treated, polymer of methyl penta
proximately 50 parts by weight of the polymerv
were dissolved in 1000 parts by weight of a good 40 4. An improved lubricant comprising in com
lubricating oil which had a. viscosity at 100° F. of
bination a hydrocarbon oil and a solute therein
'
diene.
128 S. S. U., a viscosity at 210° F. of 42 S. S. U. and
plate, approximately 50 parts by weight of pow- .
- dered yellow phosphorous pentasul?de (Pass) was 45
the mixture being well stirred during the heating
*
comprising .5 to 20% of a cyclicized, phosphorous
“v”. I. of 109. When the solution was about com- .
added and well stirred in. The mixture was then
heated to a temperature of 180° C. for 60 minutes,
'
pentasul?de treated, polymer of Z-methyl palate
cliche-1,3.
‘
5. An improved lubricant comprising in com
bination a hydrocarbon oil and a solute therein
comprising .5 to 20% of a cyclicized, phosphorous '
pentasul?de treated. polymer of myrcene.
v
period. At the end of the 60 minutes the mixture
6. An improved lubricant comprising in comwas cooled to approximately 35° C. and ?ltered 50 bination a hydrocarbon oil and a solute therein
through a paper ?lter to remove residual traces
‘comprising .5 to 20% of a cyclicized, phosphorous
of, uncombined phosphorous pentasulilde'and to
pentachloride treated, polymer of allo-ocymene.
yield a clear ?ltrate.v The ?ltrate was then blown
7. The method of preparing a lubricant com
with air, using about 5 cubic feet per hour per
prising the steps in combination of polymerizing
kilo of solution for a period of 2 hours to remove‘ 55 a polyole?n having from 6 to lé'carbon atoms
traces of hydrogen sul?de and to deodorize the
per molecule‘cyclicizing the polymer, treating
oil.
_
'
the cyclicized polymer with a compound of plies
Chemical anaylsis or the clear, odorless ?ltrate
phorous and an element from the sulfur group
and dissolving .5 to 20% of the cyclicized phos
showed that it contained 0.8% of combined phos
‘ phorousand 2.88% of combined sulfur. Viscosity 60 phorous compound treated polymer in a lubricat
ing material. .'
I
'
determinations and viscosity index determine: tions showed the 'followinginspection results;
~8. The method of preparing a lubricant com“
prising the steps in combination of polymerizing a.
polyole?n having from 6 ‘to 14 carbon atoms per
s. s. U. at
s. s. U. at
v.1.
1000 F.
210° F.
65 molecule, cyclicizing the polymer, dissolving the
cyclicized polymer in a hydrocarbon liquid, treat
ing the cyclicizec‘ polymer with a compound or
phosphorous and an element from the sulfur
These determinations show that the resulting oil
group and dissolving .5 to 20% of the cyclicized
has an excellent viscosity and an excellent viscos 70 phosphorous compound treated polymer in a. lu
284
58
134
ity index.
Portions of this oil were then charged into the
Almen machine for the shock loading test. All
15 weights (2 lbs. each) were placed on the arm
and allowed to drop simultaneously. The 011 car
bricating material.
9. The process of preparing a lubricant come
prising the steps in combination of polymerizing
a methyl pentadiene, cyclicizing the methyl pen
75 tadiene, dissolving .5 to 20% of the cycliclzeo
2,408,575
9
v
methyl pentadiene in a. hydrocarbon lubricant,
_ and treating the dissolved polymer with phos
phorous pentasul?de. _
10. The process of preparing a lubricant com
prising the steps in combination of polymerizing v
a. methyl pentadiene, cyclicizing the methyl pen
tadiene by the application thereto of p-sulfonic
acid, dissolving .5fto 20% of the cyclicized methyl
V
10
7
11. The process oi.’ preparing a lubricant com
prising the steps in combination of polymerizing
a. methyl pentadiene,'cyclicizing the methyl pen
tadiene by the application thereto of stannlc chlo
ride, dissolving .5 to 20% of the cyclicized methyl
pentadiene in a hydrocarbon lubricant and treat
ing the dissolved polymer with phosphorous pen
tasul?de.
1
'
pentadiene in a hydrocarbon lubricant, and treat
DAVID W. YOUNG.
ing the dissolved polymer with phosphorous pen-_ .10‘
HARRIS D. HINELINE.
' tasul?de.
w
-
_
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