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Патент USA US2403453

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Patented July 9, 1946
2,403,453
UNITED STATES PATENT OFFICE "
2,403,453
man. on. comosmon
Ferdinand Philip Gtto, Woodbury, N. 3., asslgnor
to Socony-Vacimm Oil Company, Incorporated,
a corporation of New York
No Drawing. Application September 9, 1M2,
Serial No. é??td
(Cl. 252-m-5L5)
19 Claims.
i
This invention has to do with the improvement
specific type of oil, such as a moderately re?ned
of mineral oil fractions by the use of a novel
oil,
The present invention is predicated upon the
class of reaction products or compounds which,
when admixed with such a mineral oil in minor
discovery of a class 'of reaction products or com
proportions, will prevent or delay undesirable
pounds which possess the property of stabilizing
all mineral oil fractions against the deleterious
effects of oxidation. The improving agents con
templated herein are obtained by the reaction of
changes taking place in the oil.
As is well known to those familiar with the
art, substantially all the various fractions ‘ob
tained from mineral oils and re?ned for their
hydroxyaromatic compounds; ammonia and alde
various uses are susceptible to oxidation. This 10 hydes having more than one carbon atom. Of
susceptibility and the manner in which oxidation
this broad class of reaction products or com
manifests itself within the oil varies with the type
pounds, however, two sub-classes are preferred.
and degree of re?nement to which the oil has
One such sub-class of reaction products is that
been subjected and with the conditions under
obtained by the reaction of substantially‘ one
which it is used or tested. In other words, the 15 equivalent of a hydroxyaromatic compound, one
products formed in an oil fraction as a result of
equivalent of ammonia and two equivalents of
oxidation and the degree to which they are
said aldehyde. Particularly preferred are those
formed depends upon the unstable or catalytic ‘ reaction products of a second sub-class which are
constituents present in the unre?ned oil, and the
obtained by the reaction of substantially one
extent to which these various unstable constit 20 equivalent of a hydroxyaromatic. compound and
two equivalents of an aldehyde-ammonia con
uents or constituents which may act as oxidation
catalysts have been removed by the re?ning
treatment.
The use of oxidation inhibitors for the purpose
of stabilizing mineral oil fractions against the
deleterious effects of oxidation is well known. As
the action of these inhibiting materials is appar
ently catalytic, the problem of their development
densation product. Reaction products of this
latter and particularly preferred sub-class are'
less resinous, and, accordingly, more soluble than
the other reaction products or compounds broadly
contemplated herein.
Typical hydroxyaromatic compounds contem
plated for use as one of the three reactants are:
phenol, cresol, ethyl phenol, diamyl phenol, wax
large degree by the oxidizable constituents which 30 phenols. a-naphthol, p-naphthol, wax-alpha- and
is a difficult one and is evidently in?uenced to a
are in the oil following a particular re?ning treat
ment. For example, a particular inhibitor, or
class of inhibitors may be e?ective to stabilize a
highly re?ned oil (one refined with large quanti
ties of fuming sulfuric acid) against acid forma 35
tion while the same inhibitor may have no appre
beta-naphthols,
etc.
Long - chain aliphatic
groups having more than twenty carbon atoms
and obtained from petroleum waxes are referred
to herein as "wax” groups, and are contemplated
herein as preferred substituents of hydroxyaro
matics 'as indicated above.
.
ciable effect upon acid, color or sludge formation
in a moderately re?ned oil (such as one re?ned
with a moderate quantity of sulfuric acid), and
As de?ned above, the reaction products or com
pounds contemplated herein have as one of the
three reactants an aldehyde having more than
vice versa. This same inhibitor may or may not 40 one carbon atom. In short, all aldehydes other
be effective in inhibiting acid, sludge, and color
than formaldehyde are contemplated herein.
formation in a solvent-re?ned oil and may or
For example, my particularly preferred class of
may not be effective to inhibit the corrosive ac
reaction products or compounds is that obtained
tion of a solvent-re?ned oil toward metals such
‘ by the reaction of one equivalent of a hydroxy
as, for example. the various normally corroded 45 aromatic compound of the group above, and two
alloys typi?ed by those used in cadmium-silver
equivalents of an aldehyde-ammonia condensa
bearings.
tion product. Formaldehyde does not react with
Numerous compounds and compositions have
ammonia in the same way, and, accordingly, does
not yield similar products, as do other ?dehydes.
fractions. Typical of such inhibitors are those 50 Representative aldehydes which may be used to
formed by reactions of various amines and alde
obtain the reaction products or compounds con
been proposed for use as inhibitors in mineral oil
hydes, and of various amines, aldehydes and hy
»7 templated hereinare acetaldehyde, buisrralde
droxyaromatic compounds. Inhibitors of this
hyde, furfuraldehyde, henzaldehyde, toluic aide“
class, or classes, are of varying degrees of 'e?ec
hyde, etc.
_
_
tiveness and are, in general, e?ective only in a E5
Several typical procedures by which the reamx
2,403,453
3
4
tion products or compounds contemplated herein
may be prepared are described by the following:
EXAMPLE ‘IV
DIAHYL PHENOL—ACETALDEH'YDE-AHHONIA
Two hundred cc. of 95% ethyl alcohol satu
rated with ammonia at 15° C. was added drop
wise to a mixture oi 117 grams (0.5 mol) of
diamyl phenol, 54 grams (1.2 mols) of acetalde
hyde, and 200 cc. of absolute ethyl alcohol at
.
'
ExAMeLE 1
BzrA-NAPnrnoL-BsmLnEnYnE-AMMONIA
One mol, 144 grams, of beta-naphthol was dis
. solved in 220 cc. of 95% ethyl alcohol and to this
solution two mols, 212 grams, of benzaldehyde
approximately 10° C. The mixture was allowed
were added. Then, 200 cc. of 95% ethyl alcohol 10 to stand at room temperature for two days and
saturated with ammonia was added. The reac
was then “topped” to 115° C. with vacuum to ob
tion vessel was then closed and the reaction al
tain the ?nished product, a viscous, light-brown
lowed to continue for two hours, after which time
oil containing 3.04% nitrogen.
the reaction vessel was opened. Unreacted am
monia was allowed to escape and the reaction
EXAIVIPLEV
mixture so formed was allowed to stand for about
twelve hours.
The condensation product which
separated in the form of white needles was ?l
tered with suction, and washed with 50 cc. of al
DIAMYL PHENOL AND ACETALDEHYDE-AMMONIA
(a) Acetaldehyde-ammonia
Gaseous ammonia was passed slowly into a
cohoL The condensation product contained 20
solution of 100 grams of acetaldehyde in 150
about 4.2% of nitrogen in addition to carbon, hy
cc. of ether for about two hours. The tempera
drogen and oxygen,
ture, during the ammonia addition, was main
EXAMPLE II
tained below 150° C. by cooling the reaction vessel
by means of an ice-bath. The crystalline precipi
DIAMYL PHENOEBENZALDEHYDE-AMMONIA
25 tate of acetaldehyde-ammonia was ?ltered from
the reaction mixture by suction, washed several
Gaseous ammonia was introduced into a mix
times with ether and then dried in a desiccator.
ture of 50 grams (0.21 mol) of diamyl phenol,
45.3 grams (0.42 mol) of benzaldehyde and 100
(b) Diamyl phenol and acetaldehyde-ammom‘a
grams of 95% ethyl alcohol at room temperature. 30
One-half a mol (117 grams) of diamyl phenol,
After about twenty minutes the temperature rose
300 cc. of absolute alcohol and 61 grams of
to 115° F., and during the following hour fell to
acetaldehyde-ammonia, obtained above in V(a),
95° F., after which the introduction of ammonia
were mixed together and the mixture warmed to
was discontinued. The mixture was then grad
ually heated to 150° F. and maintained at'this 35 45° C. The mixture was then allowed to stand
in a stoppered ?asklat room temperature for 24
temperature for about 1% hours.‘ The mixture
was then allowed to cool and stand at room tem
perature for a few days. The reaction mixture
hours. The mixture was then ?ltered and the
?ltrate was “topped" to 110° C. with vacuum to
obtain the product, a light-brown oil containing
was then diluted with benzol, water-washed and
“topped" to 210° C. at 5 mm. pressure in order to 40 3.46% nitrogen.
remove solvents and unreacted materials. The
EXAMPLE VI
reaction product contained~3.76% nitrogen.
EXAMPLE m'
ALPHA-‘NAPHTHOL AND BENZAlZ-DEHYDE-AMMONIA
(a) BenzaZdehyde-ammonia
WAx-BErA-NAPnmoL (3-_-16) AND ‘Acn'rsnnenrnn
Amuom
Seven grams of acetaldehyde-ammonia, ob
tained above in V(a), 150 cc. of benzol, 35 cc. of
ethyl alcohol and 50 grains of wax-beta-naph
Concentrated NH4OH, 200 00., was added drop
thol (3-16) obtained according to the procedure
wise to a solution of 106 grams (1 mol) of hen
outlined
in U. S. Patent 2,197,834 were mixed
zaldehyde in 100 cc. of 95% ethyl alcohol. The 50 together and the mixture warmed to 45° C. The
reaction mixture during this addition was cooled
mixture was then allowed to cool to room tem
by means of an ice-bath which was removed
perature and allowed to stand at room tempera
after the addition was complete. When the mix
ture for about 16 hours. It was then ?ltered
ture was at room temperature, the crystals which
and the ?ltrate was “topped” to 150° C. with
had deposited were ?ltered and washed with 55 vacuum to obtain the finished product which con-' ‘
alcohol.
tained 1.02% nitrogen.
_
(b) Alpha-naphthol and benzaZdehyde-ammonia
EXAMPLE VII
The benzaldel'iyde-ammonia, 149 grams, ob
,s-NAPnrHoL AND ACETALDEHYDE-AMMONIA
tained above in 3 (a) was mixed with v72 grams 60
(0.5 mol) of alpha-naphthol and 200 ‘cc. of 95% >
A mixture of 72 grams of p-naphthol, 66
ethyl alcohol. The mixture was warmed on a
grams of acetaldehyde-ammonia, obtained as
steam-bath until the evolution of ammonia was 4
in V(a), and 200 cc. absolute ethyl alcohol
noticed, On standing overnight at room tem
was warmed gently to 45° C. and then al
65
perature, a brown resinous material deposited in
lowed to stand for two days in a stoppered ?ask
the reaction vessel. Alcohol was decanted off and
at room temperature. The ?ask containing the
the product was washed with fresh hot alcohol.
product was. then placed in an ice-salt bath in
The alcohol suspension was cooled, whereupon
order to precipitate the product, a white amor
the product solidi?ed. The amorphous mass so
phous material. On reprecipitating from ethyl
obtained was a light brown powder when pul 70 alcohol, a crystalline product was obtained. Re,
verized. It was washed several times with small
crystallization from ethyl alcohol gave a white >
portions of alcohol to remove unreacted materi
crystalline product which contained: 6.47% ni
als. As with all the reaction products contem
trogen', 78.63% carbon and 6.63% hydrogen.
plated herein, this product contained nitrogen
The effectiveness of the reaction products or
in addition to carbon, hydrogen and oxygen.
compounds contemplated herein is demonstrated
‘ 2,408,453
by the results of the following tests on oil blends
containing small amounts of said reaction prod
In the foregoing table, the data clearly demon- states the superiority of the reaction products,
ucts or compounds, and on the oils alone. Re
sults are also provided below for individual re
actants, or for reaction products of only two of
the three necessary reactants for the reaction
contemplated herein over the individual reactants
and the partial reaction products, those of only
two of the individual reactants. For example,
diamyl phenol does not improve the oil in thisv
products contemplated herein, in order to indi
corrosion test, in ‘fact, corrosion increases from
, cate the superiority of the contemplated reaction
35 to 44 mgms.; whereas, the same quantity, 113%,
of the reaction product of diamyl phenol, benz
products over said reactants and said partial re
action products. It will be noticed that, as afore 10 aldehyde and ammonia reduces corrosion in the .
said, these improving agents are eifective in more
test from 35 to 4 mgm's. Similarly,_the results
than one type of oil, illustrative of which are
indicate that the beta-naphthol-benzaldehyde
the moderately refined and solvent re?ned oils
ammonia reaction product is greatly superior to
beta-naphthol and to'benzaldehyde-ammonia in .
used in the tests described below.
15
EXAMPLE VIII
this test.
'
'
EXAMPLE IX
'
I
Conaosron Tasr
A distillate from a Rodessa crude was re?ned
Motor oils, especially those re?ned by certain
with IurfuraLdewaxed and filtered. It had a spe
solvent-extraction methods, tend to oxidize when 20 cific gravity of 0.856, a ?ash point of 420° F., and
submitted to high temperatures to form products
a Saybolt Universal viscosity of 151 seconds atv
that are corrosive to metal bearings. This corro
100° F. It is suitable for use in turbines. It was
sive action may be quite severe with certain bear
tested as follows:
‘
ings, such as those having the corrosion-suscepti
Twenty-?ve cc. samples of the oil were heated
bility of cadmium-silver alloys and may cause
to 200° F., with 5 liters of air per hour bubbling
their failure within a comparatively short time. 25 through them. Twenty-four inches of No. 18
The following test was used to determine the cor
gauge copper wire and 1 gram of iron granules
rosive action of a motor oil on an automobile
were added to each sample. Also, 22 cc. of distilled
connecting rod bearing of the cadmium-silver
alloy type.
water were added each day. The samples were
and residuum stocks separately refined by means
of chlorex and then blended with an S. A. E. 20
motor oil with a speci?c gravity of 0.872, a ?ash
Table II below:
point of 435° F., and a Saybolt Universal viscosity
Reaction product
' tested for acidity (N. N.), color, and ‘sludge after
The oil used consisted of Pennsylvania neutral 30 varying periods of time. Results are‘ given in
.
of 318 seconds at 100° F. The oil was tested by ‘’
Table II
added
1501' cent Time,
used
N
hrs.
‘
'
Lov.
Sludge,
color
mg./25 cc.
adding a section of a bearing containing a cad
mium-silver alloy surface and weighing about 6
None _____
grams, and heating it to 175° C. for 22 hours while
a stream of air was bubbled against the surface
of the hearing. The loss in weight of the bearing
during this treatment measures the amount of
corrosion that has taken place. A sample of the
oil containing the improving agent was run at the
Alpha-naphthol
________________ __
Alpha-naphthol_--__
Mo
165
a). s
320
251
1, 006
19. 1
147
199
benzaldehydeammonia _______ ._
'
M9 .
1, 102
. 0i
3
63
.
EXAMPLE X
In addition to the foregoing tests, I have also
same time as a sample of the straight oil, and vthe 45 made comparative tests between an oil and an
loss in weight of the bearing section in the in
- oil blend containing a representative improving
hibited oil can thus be compared directly with the
loss of the section in the uninhibited oil. The
results obtained in this test are set forth in Table
I below.
agent of the type contemplated herein to deter
mine the comparative behavior of the unblended
‘ oil and the improved oil under the actual operat
60 ing conditions of an automotive engine._ The
tests were carried out in a single-cylinder Lau
Table I
son engine operated continuously overla time
Mgs. loss in weight
Reaction product added
Pgrsggnt
Inhibited
Diamyl phenol ___________________ __
Uninhib
ited
M
44
V4
4
35
Mo
46
35
stock of 45 seconds Saybolt Universal viscosity ‘
ammonia _______________________ ..
Alpha - naphthol - henzaldehyde ammonia _______________________ __
Mo
4
35
at 210° F., and the results obtained are listed in
M
2
35
Benzeldehyde-ammonia- _ _ _ _
l4
12
46
Ho
23
46
Diamyl phenol-benzaldehyde-
35
interval of 16 hours with the cooling medium
held at a temperature of about 212° F. and the
65 oil temperature held at about 280° F. The en
sine was operated at a speed of about 1,830
B. P. M. At the end of the test, the oil was tested _
for acidity (N. N.), and viscosity.
.
The oil used in the test was a lubricating oil
-
monia ...................... __
Beta-naphthol ______________ ..'..-.__
Beta - naphthoi - benzaldehyde -
o ........................... _.
Beta-naphthol and benzaldehyde
ammonia _______________________ -_
D0... ......................... __
Alpha-naphthol and benzaldehyde
Do
Diamyl phenol and acetaldehyde
ammonia ....................... _D0 ___________________________ __
Wax beta-naphthoi (3-16) and
acetaldehyde-ammonia _________ ._
$4
1
46
Mo
2
46
i4
1
46
Mo
2 _.
46
i4
0
39
Me
8
39
3/4
0
31
Mo
1
31
i4
2
32
31
Bcta-naphthoi and acetaldehyde- {
V4
0
ammonia _______________________ _.
Mo
6
31
v Table III below:
Table ‘In
Reaction product added
P3223“ N. N. 2?6°%§_¥s‘eg_)
None _____________________________________ _ _
5. l
49. 9
Alpha - naphthol - benzaldehyde -
l. 5
45. 7
ammonia _____________________ _ _
1%
~
as:o
As indicated by the foregoing examples, the '
proportion of the improving, agents contem
plated herein to effect the desired improvement
is small.
The amounts used may, of course, be‘
W varied, depending upon the oil, the conditions of
-
2,403,458
use, etc., but in general, the desired results can
be obtained with an amount of improving agent
ranging from about 0.1 per cent to about 1.0 per.
cent by weight of the oil.
It is to be understood that while I have de
reaction product obtained by the reaction of sub
stantially one equivalent of diamyl phenol, two
equivalents of acetald'ehyde and one equivalent
scribed in detail several preferred procedures
which may be followed in the preparation of the
.prising a mineral oil and in- admixture there
with a minor proportion, su?icient to stabilize
reaction products or compounds contemplated
said oil against the deterious effects of oxidation,
herein as oil-improving agents and have referred
of the reaction product obtained by the reac
tion of substantially one equivalent or a mono
to various representative constituents which
may be used in the preparation, of these reaction
products or compounds, such procedures and ex
amples have been used for illustrative purposes
only. The invention, therefore, is not to be con
sidered as limited by the speci?c examples pro
vided but includes within its scope such changes
and modi?cations as fairly come within the
spirit of the appended claims.
,
of ammonia.
.
8. An improved mineral oil composition com
hydroxyaromatic compound, two equivalents of
an aromatic aldehyde having more than one
_ carbon atom and one equivalent of ammonia.
9. An improved mineral oil composition com
prising a mineral oil and in admixture therewith
a minor proportion, su?icient to stabilize said
oil against the deleterious effects of oxidation,
of the reaction product obtained by the reaction
of substantially one equivalent of a mono
I claim:
1. An improved mineral oil composition com 20 hydroxyaromatic compound, two equivalents of
benzaldehyde and one equivalent of ammonia.
prising a mineral oil and in admixture therewith
10. An improved mineral oil composition com
a minor proportion, su?icient to stabilize said oil
prising a mineral oil and in admixture there
against the deleterious e?ects of oxidation, of the
with a minor proportion, su?icient to. stabilize
reaction product obtained by the reaction of sub
said oil against the deleterious effects of oxida
stantially one equivalent of a mono-hydroxy
tion, of the reaction product obtained by the re
aromatic compound, two equivalents of an alde
action of substantially one equivalent of diamyl
hyde having more than one carbon atom and
phenol,‘two equivalents of benzaldehyde and one
one equivalent of ammonia.
.
equivalent of ammonia.
—
'
2. An improved mineral oil composition com
11. An improved mineral oillcomposition com
prising a mineral oil and in admixture therewith 30
prising a mineral oil and inladmixture there
a minor proportion, su?icient to stabilize said oil
with a minor proportion, su?icient to stabilize
against the deleterious e?ects of oxidation, of the
said oil against the deleterious effects of oxida
reaction product obtained by the reaction of sub
tion, of the reaction product obtained by the
stantially one equivalent of a mono-hydroxy
reaction of substantially one equivalent of a
aromatic compound and two equivalents of ‘an
mono-hydroxyaromatic compound and v two
aldehyde-ammonia reaction product wherein the
aldehyde has more than one carbon atom.
3. An improved mineral oil composition com
equivalents of an-aliphatic aldehyde-ammonia
reaction product wherein the aliphatic aldehyde
has more than one carbon atom.
prising a mineral oil and in admixture therewith
12. An improved mineral oil composition com
a minor proportion, sumcient to stabilize said oil 40
prising a mineral oil and in admixture there
against the deleterious e?ects of oxidation, of the
with a minor proportion, sufficient to stabilize
reaction product obtained by the reaction of sub
said oil against the deleterious effects of oxida
stantially one equivalent of a mono-hydroxy
tion, of the reaction product obtained by the
aromatic compound, two equivalents of an ali
phatic aldehyde having more than ‘one carbon 45 reaction of substantially one ‘equivalent of a
mono-hydroxyaromatic compound and two
atom and one equivalent of ammonia.
equivalents of an acetaldehyde-ammonia reac
4. An improved mineral oil composition com
tion product.
‘
prising a mineral oil and inadmixture there
13. An improved mineral oil composition com
with a minor proportion, sui?cient to stabilize
said oil against the deleterious effects of oxida 50 prising a mineral oil and in admixture there
with a minor proportion, sufficient to stabilize
tion, of the reaction product obtained by the re
said oil against the deleterious e?ects of oxida
action of substantially one equivalent of a mono
tion, of the reaction product obtained by the
hydroxyaromatic compound, two equivalents of
reaction of substantially one equivalent of an
acetaldehyde and one equivalent of ammonia.
'5. An improved mineral oil composition com 55 alkyl-substituted mono-hydroxyaromatic com
pound and two equivalents of an aldehyde-am
prising a mineral oil and in admixture therewith
monia reaction product wherein the aldehyde
a minor proportion, sufficient to stabilize said oil
has more than one carbon atom.
against the deleterious effects of oxidation, of the
14. An improved mineral oil composition com
reaction product obtained by the reaction of sub
stantially one equivalent of an alkyl-substituted 60 prising a mineral oil and in admixture there
with a minor proportion, sui?cient to stabilize
hydroxyaromatic compound, two equivalents of
said oil against the deleterious effects of oxida
an aldehyde having more than one carbon atom
and one equivalent of ammonia.
6. An improved mineral oil composition com
tion, of the reaction product obtained by the
reaction of substantially one equivalent of diamyl
' prising a mineral oil and in admixture therewith 86 phenol and two equivalents of an aldehyde-am
monia reaction product wherein the aldehyde
a minor proportion, suf?cient to stabilize said oil
- against the deleterious effects of oxidation, of the
reaction product obtained by the reaction of sub
stantia y one equivalent of diamyl phenolqtwo
has more than one carbon atom.
15. An improved mineral oil composition com
prising a mineral oil and in admixture there
equivale ts of an aldehyde having more than one 70 with a minor proportion, su?icient to stabilize
said oil against the deleterious e?ects of oxida
carbon atom and one equivalent of ammonia.
'7. An improved mineral oil composition com
prising a mineral oil and in admixture therewith
a minor proportion, su?icient to stabilize said oil
tion, of the reaction product obtained by ‘the
reaction of substantially one equivalent of di
amyl phenol and two equivalents of an acetalde
against the deleterious e?‘ects of oxidation. of the 76 hyde-ammonia reaction product.
'
9
2,403,453
10
.
18. An improved mineral ‘oil composition com-'
16. An improved mineral oil composition com
prising 9, mineral oil and in admixture there
prising a mineral oil and in admixture there- a
with a minor proportion, sufficient to stabilize
said oil against the deleterious e?ects of oxida?
tion, of the reaction product obtained by the
with a minor proportion, sumci/ent to stabilize
said oil against the deleterious e?ects of oxida
tion, of the reaction product obtained by the
reaction of substantially one equivalent of a
reaction of substantially one equivalent ,of di
amyl phenol and two equivalents 01' a benzalde
mono-hydroxyaromatic compound and two
equivalents of, an aromatic aldehyde-ammonia
reaction product.
1'7. An improved mineral oil composition com
prising a mineral oil and in admixture there
with a minor proportion, su?icient to stabilize
said 011 against the deleterious effects of oxida
tion, of the reaction product obtained by the
hyde-ammonia reaction product.
'
_
I
19. 'An improved mineral oil composition com
prising a mineral oil and in admixture there
with from about 0.1.weight per cent to about
1.0 weight per cent of the reaction product ob
tained by the reaction oi’ a mono-hydroxyaro
matic compound. an aldehyde having more than
reaction of substantially one equivalent of a 15
compound and two
equivalents of a benzaldehyde-ammonia reac-'
one carbon atom and ammonia.
'
mono-hydroxyaromatic
FERDINAND PHILIP OTTO.
tion product.
?ertcate of Correction
Julye, 1946.
~ Patent No. 2,403,453.
FERDINAND PHILIP OTTO
It is hereby certi?ed that errors appear in the printed s eci?cation of the above
numbered patent requiring correction as follows: Column 6, inc 28, Example IX, for
“22 cc.” read .2 00.; column 7, line 61, claim?, for “hydroxyaromatic” read mono
hydrow'yaromatw ; and that the said Letters Patent should be read with these corrections
therein that the same may conform to the record of the case in'the Patent Oi?ce.
Signed and sealed this 29th day of October», A. D. 1946.
lewd
r»:
‘
'
FR 21:"
9
First Assistant Uommz'sst'oner of Patents.
.
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