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Patented Oct.
' 2,409,333"
2,409,333 -
LUBRICANT AND mz'rnon or rnnrsnmc ~
‘Donald. 1.."wnshawesme1a, and Charles w.
Bohmer, In, Elizabeth,’ N. J., as'simors to
Standard Oil Development‘Company, a corpo
ration of Delaware
No Drawing. ,Applleatlon'september 1a, 1943, Y
Still] No. 502,840
4_ Claims. (o1.~ 252-59)
This invention- relates to chemically resistant
decyl acrylate, amylphenyl methacrylate, iso
heptyl cy'clohexyl chloroacrylate, chlorodecyl
methacrylate, etc., especially such polyacrylic
:lubricants, and more particularly to nitration
resistant lubricants.
This application is a continuation-in-part of
esters having a molecular weight of about 10,000
application Serial No. 393,370, ?led May 14, 1941,
now U. S. Patent No. 2,335,331, issued November
30, 1943, which relates broadly to the production
to about ‘50,000 or .more. _-
_ Another case of'high molecular weight, oxy
of a nitration-resistant lubricant of proper con
sistency by. blending together a major proportion ,
gen-containing substances which can be used
for the purposes of this invention is the class of
condensation products'or polyesters of substi
.of mineral white oil, a highly re?ned petroleum 10 tuted fatty acids having the general formula,
wax'and a substantially saturated linear type
aliphatic hydrocarbon polymer having a molec
ular weight of about 5,000 to 100,000, or higher.
1 '
2': (CH1) .——( 1‘ )—(CH:) .]—0 0 OH
*- The chief feature vof the present continuation
_ in-part application is_that in place of hydrocar
bon polymers in‘ the above described composi-_
tions, one may use high molecular weight oxy
gen-containing viscosity-increasing’ linear ali
phatic polymers, preferably having a molecular
weight of at least 1,000. > One such oxygen-con
taining thickener is a; high molecular weight
polymer of an oxygen-containing compound hav
ing the group
_ '
15~ in which Ris a mom or anunsubstituted or sub
stituted aliphatic, aromatic, or hydroaromatic
group, a: and 11 may equal 0 or any integer pro
‘ vided that :I:+:I/v equals'at-least 5, and where n is
0 or an integer and 711 is a whole number and Z '
20 is a functional group which has one replaceable
hydrogen atom, Z being capable of esterifying a
carboxyl group.
Some of these polyesters are
’ described in U. S. Patent 2,147,647, andare typ
i?ed by the polyester having‘a molecular weight
of about 14,000 obtained by polyesteri?cation of
in its molecular structure.- Such additives in
12-hydroxy stearic acid in the presence of a small
clude polymers of vinyl ethers having the gen
amount of adipic acid,
eral formula
One may use still other_thickeners such as .
various isobutylene co-polymers of‘ high- molec
ular weight, e..g., 5,000 to 50,000 or more, such
‘as the almost ‘saturated _ isobutylene-butadiene _
co-polynier made at temperatures below ‘0° 0.,
e. g. ——70° 0., —80° 0., etc., using as'catalyst a
‘R2 is a hydrogen atom or a substituted or un
solution of a Friedel-Qraft halide dissolved in an
substituted aliphatic radical e. _ g... ‘vinyl oleyl 35, . alkyl halide solvent, e. g., AlCla in methyl chlo
ether, vinyl isobutenyl ether, ,vinyl meta-cresyl
ride, and‘preferably in the presence of lique?ed
‘ether, vinyl cyclohexyl ether, vinyl octadecyl
propane, ethane, ethylene or other inert gas as
_ in which R1 is an unsubstitutedor substituted ali
phatic, aromatic, or hydroaromatic radical; and
ether, vinyl chloroethyl-ether, vinyl amino propyl
refrigerant-diluent. Another suitable co-poly?
ether, a-ethylvinyl isohexyl ether, a-ChlOl‘O
mer thickener is the oil-soluble, substantially
methyl vinyl lauryl' ether, etc'.; polymers of vinyl 40 saturated isobutylene-ethylene co-polymer made
esters having the general formula
at 100-400° C., using high pressure, e. g., 500,
1,000, or 2,000 atmospheres, preferably'with ad
dition of a small amount of oxygen. Other types
in which R1 and R2 are as above and 11 is an in
of substantially fully saturated polymeric hydro,
teger having ‘a value of 1 or‘ more, e.‘ g., vinyl 45 vcarbon materials may be used such-as substan
\_ tially completely hydrogenated rubber. In gen
stearate, vinyl‘ ester of acids obtained by oxida
tion of parai?n wax, vinyl chloropropr'ionate,
vinyl aminopalmitate, vinyl adipate, vinyl citrate,
eral, the various polymer thickeners to be ‘used, "
according to this invention, should have an iodine
etc.; polymers of acrylic acid esters having the
number of not more than about 20 and prefer
general formula, R—OOC—C(X) =CH2, in which 50 ably not more than 10, those having ‘an iodine
R is an unsubstituted’ or substituted aliphatic,
number of less than 1 or 2 being the most pref
aromatic, or hydroaromatic group, preferably
containing at least 10 carbonatomsand X is a H
or a halogen atom, 013a. CH3 group or a CzHs
Although the invention‘has been particularly‘
emphasized as valuable as a nitration-resistant
group, e. g. lauryi acrylate, cetyl‘acrylate, octa-' 55 lubricant, it is intended that this lubricant be
as resistance to various acids other than nitric.
e. an; sulfuric, hydrochloric,~ eta. strong alkalies,
to its melting point of 60° C., and stirring the
polymer which dissolves readily. 6 grams of
ing and reducing agents or other chemical in
blend was made by heating the petroleum Jelly
such as caustic soda or potash,- or various oxidiz-J
solved in 10% concentration in an artiiicialpetro
leum jelly, such as used in the test shown in Table
l oi! application Serial No. 393,370, now ‘D’. 8. Pat
ent No. 2,335,331, issued November 30, 1943, The
industrial applications where ,
chemical resistance generally is required, such
the resultant blend were then mixed with 4 grams
To illustratethe application of the invention
oi’ fuming nitric acid at 60° C. No fumingoc
using a high molecular weight oxygen-containing
polymer. the following table of examples is given,‘ 10 curred and there‘ was only a 15-20° 0. temperature
rise, which is within the normal range for mate
in this instance the polymerized lauryl alpha
rials which are satisfactory for lubricating nitric
acid pump packing. This is very surprising, be
cause most chemists would expect that a chemical
15 compound containing oxygen. especially in an es
Example No.
ter linkage, would react vigorously, if not actually
about 10,000 average mol.wt.) .......... .. 10
M eral white oil (vis. about 300-400 scc./ ~
violently, with nitric acid. Although the reason ,
is not understood for the chemical inertness oi '
these high molecular weight oxygen-containing
Polymerized lauryl alpha methacrylate
. ................................. _-
___________________________________ __
Pera?ln wax (M. Pt. about 125° F.) ....... ._
Petrolatum (light colored and highly re?n
20 polymers, it is believed that the linear structure
' and relatively extremely high molecular weight,
3 ..._
______ __
compared to-esters of only monomeric or dimeric
nature as having a molecular weight in the range
up to about 500, probably have the tendency to
25 reduce the relative sensitivity of the oxygen-con
taining group in the very large molecule. When
Although preferred proportions have been
subjected to the bomb explosion test described in
' given for the amounts of mineral white 011, light
connection with Table l of our copending'appli
cation Serial No. 393,370, now‘ U. S‘..Patent No.
petrolatum and parai?n wax, it should be under
stood that in the broader aspects of this inven
tion, it is not necessary to use all three of those 30 2,335,331, issued November 30, 1943, the lubricants
prepared according to the present invention do
constituents, provided the proper texture or plas
not crush the lead ‘supporting block more than
ticity can be obtained with any one (as may be
done frequently with petrolatum), or with any
0.1 inch when tested with concentrated nitric acid
alone and able. 8 detonavtlng cap.
two of such ingredients (as with a mixture of
The compositions of thepresent invention may
mineral white-oil and param'n wax, or a mixture
also be used for the manufacture of packing ma
of mineral white oil and petrolatum) '. In the ap
terials suitable for pumps handling nitratin'g
acids. Such packing material may, for instance,
consist of acid-resistant Blue African asbestos
to mean any one or two or all three of those con
stituents. In general, the proportions of those 40 impregnated with a nitration-resistant lubricant
comprising a substantially saturated aliphatic
constituents are preferably chosen between the
oxygen-containing polymer having a molecular
approximate limits of 50 'to 85% by weight 'of
weight of at least about 5,000.
mineral white oil, 10 to 50% by weight of petro
It is not intended that this invention be limited
latum and 0 to 10% by weight of paramn wax.
to any of the particular examples which have
'l‘he proportions of oxygen-containing polymer
been given for the sake of illustration nor un
used with advantage may vary within the limits
necessarily by any theories as to the operation of
of 0.3% and 50% by weight of the lubricant to
the invention, but only by the appended claims
be improved. Good results are generally obtained
in which it is intended Ito claim all novelty in
when the amount of polymer ‘is selected in‘ ac
_‘cordance with its molecular weight as indicated 50 herent in the invention as broadly as the prior art
pended claims the expression “texture-control
ling petroleum hydrocarbon mixture” is intended
in the table below:
We claim:
1. A chemically resistant lubricant having ap
mol. wt. oi
' 5000
proximately the following composition in percent
55. by
Mineral white oil _____________________ __ 50-85
Petrolatum (light oil-free) ____________ _- 10-50
Para?ln wax ___________ _.'.. ____________ __
60 and an amount of arviscosity-increasing linear
polymer of an oxygen-containing aliphatic com
pound, said amount being selected according to.
Thus, lubricants having highly desirable prop- '
erties may be composed of the constituents and
in the proportions listed below:
the average molecular weight of said polymer,
indicated by the following table:
Polymerized acrylic acid ester __________ .... 10-15
Average mol.
Percent b
wt. oi’ polymer
Mineral whiteoil _____________________ __ 65-80
Light petrolatum _____________________ ..- 15-30
Para?ln wax ____- ___________________ _____
5, 000
12, 000
30, 000
The following test shows the nitration-resistant
80, 000
150, 000
0. 3-2
' characteristic of polymerized lauryl methacrylate: -
The dry plastic polymer, estimated to have an
average molecular weight of about 30,000, was dis 75
2. Lubricant according to claim 1 in which the
mathematical product of the percent of polymer
proximately the following' composition in percent
times the average molecular weight thereof is at
by weight:
least 50,000.
3. Lubricant according to claim 1 which when
Polymerized acrylic acid ester __________ __ 10-15
subjected to the bomb explosion test described,
does not crush the lead supporting block more
' Light petrolatum _____________________ __ 15-30
than 0.1 inch when tested with concentrated ni
tric acid alone and a. No. 8 detonating cap.
4. A nitration-resistant lubricant having ap
Mineral white oil _____________________ __ 65-80
Paraffin wax _________________________ __
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