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Патент USA US2121618

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2,121,618
Patented June 21, 1938
UNITED STATES PATENT OFFICE
2,121,618
PRESERVATION OF RUBBER
Ira Williams, Woodstown, N. J ., and Arthur Mor
rill Neal, Wilmington, DeL, assignors to E. I.
du Pont de Nemours & Company, Wilmington,
Del., a corporation of Delaware
No Drawing. Application March 19, 1932,
Serial No. 600,054
18 Claims.
This invention relates to the preservation of
rubber and more particularly to a new class of
compounds which when incorporated in the rub
ber tend to inhibit that deterioration of rubber
5 which is due to the action of heat, light and
oxidation.
Many substances have heretofore been pro
posed for incorporation into rubber for retarding
the deterioration which rubber normally under
10 goes when exposed to light, heat and air. Among
such compounds which have been successfully
used heretofore for this purpose, are certain or
ganic nitrogen compounds such as the amines
and particularly the secondary aromatic amines.
15
An object of this invention is to provide rub
ber having improved age-resisting properties. A
further object is to provide a new class of deterio
ration inhibitors for rubber. Still further and
other objects are to provide a new composition
20 of matter and to advance the art. Other ob
jects will appear hereinafter.
These objects are accomplished by the follow
ing invention which comprises incorporating with
rubber a compound of the class represented by
25 the formula:
H
l
(Cl. 18-50)
In order to more clearly point out the advanta~
geous results obtainable with this new class of
compounds, stocks were prepared according to
the following table:
Table I
5
10
Smoked sheets _____ __
Zinc oxide _____ __
Dlphenyl guanidine.
Benzul benzid'
Dibenzyl benzidine_ .
Benzyl tolidine. _ _ __
Benzyl dianisidine _____ _.
These stocks were vulcanized to a comparable
state of cure and then were subjected to an ac
celerated ageing test in which vulcanized slabs 20
of the various stocks were suspended in a Geer
oven maintained at 70° C. in a constantly re
newed stream of air.
The results of this test
are given in the following table:
Table II
25
H
R—II\T—-A—~ILT—~R1
- -
The term “diphenyl nucleus”, as employed in
the speci?cation and claims, is to be understood
-
-
n1 Gcer oven
tens?e
in which R represents an. alkyl or aralkyl group,
R1 represents hydrogen or an alkyl or aralkyl
group and A represents a diphenyl nucleus.
The term “aralky ” as employed in the speci
?cation and claims is to be understood to mean
an aliphatic group in which one or more of the
hydrogen atoms are replaced by an aryl group
35
or groups which may. have one or more alkyl
groups substituted in the aryl group or groups.
After 10 days
Original
Stock
tensile
30
4100
3715
3965
4160
4000
_
542
2880
2520
2400
3270
.
40 to mean two phenyl groups directly connected
together and either one or both of which may
have an alkyl or alkoxy group substituted in the
40
Stocks
ring.
A
These compounds may be prepared by heating,
45 either with or without a solvent, benzidine or a
substituted benzidine, such as ortho tolidine or
ortho dianisidine, and an aralkyl or alkyl halide,
such as benzyl chloride or butyl chloride.
Some of the compounds which we have found
to possess the property of inhibiting the deterio
50
ration of rubber to a marked degree when incor
porated in the rubber are benzyl benzidine, sym
metrical dibenzyl benzidine, benzyl tolidine.
benzyl dianisidine, allyl benzidine, and butyl
benzidine.
.
.
35
In order to still further show the advantageous
effects of these compounds stocks were prepared
according to the following table:
Table III
B
o
D
E
100
100
100
190
M
10
I0
10
4
4
4
45
Smoked sheets ________________________ ._ 100
Zineoxida...
Sulfur ________ ._
__
Diphenyl guanidme...
Benzyl benzidine
Allyl benzidine-
________ __
10
________ __
4
__ .. _
_ __
'
l
.
Benzyl tolidine. _
-
Butyl benzidine__
1
These stocks were also vulcanized to a com
parable state of cure and were then tested by
hanging slabs of the various stocks in a Bierer
Davis bomb in which a constant temperature of‘ 55
2
ts.
2,121,618
70° C. and a pressure of 300 pounds of oxygen
was maintained for 48 hours. The results of these
tests are given in Table IV:
We claim:
1. Rubber having incorporated therein a small
amount of a compound having the formula
Table IV
in which A represents a diphenyl nucleus, R rep
resents a member of the group consisting of alkyl
and aralkyl groups and R1 represents a member
Original After 48 hours
tensile in bomb tensile
Stock
3500
j’ 400 '
3175
2475
3525
.
2375
3175
2350
v3050
I 1775
-‘0f- the group consisting of hydrogen and alkyl
and aralkyl groups.
2. Rubber having incorporated therein a small
amount of a compound having the formula
Other compounds of this class which merit
’
»
r i‘
i‘
15
R—N—A—N——R1
special attention are those in which R and/ or R1
in which A'represents a diphenyl nucleus, and
in the formula:
I?
R and R1 each represents an aralkyl group.
3. Rubber having incorporated therein a small
amount of a compound having the formula
20
1
R—N—A—N—R1
20
represent an aralkyl group in which the aryl con
stituent is substituted. Representative members
of this type of compound have the formula:
i’
.
.
‘i
R—N——A—N-—R1
in-which A represents a diphenyl nucleus, and
R and R1 each represents an alkyl group.
a 4. Rubber having incorporated therein a small
2,5
amount of a compound having the formula
and
.
30
.
11
.
H
om-oan-om-?Q-O ] ~CH2-Cd14-CH3
It is also possible to make compounds in which
R and R1 of the formula:
H
(n
-R>and R1 represent identical aralkyl groups.
5. Rubber having incorporated therein a small
amount of a compound having the formula
'
H
Rat-Hat.
ing forumla:
H
.
represent different groups. Representative mem
bers of this type-of compound have the follow
4O
' in which'A represents a diphenyl nucleus, and . 30
'
H
R—l]\1'—A—IlI—R1
.
in which A represents a diphenyl nucleus, and
R and R1 represent identical alkyl groups.
6. Rubber having incorporated therein a small
amount of a compound having the formula
40
H
H
alto-OM
in which R and R1 each represents an aralkyl
N—benzyl N’-propyl benzidine
and
.
_
group.
,
H
'
45
'7. Rubber having incorporated therein a small
H
amount of a compound having the formula '
N-methylbenzyl N’-benzy1 benzidinc
From the above tests it will be apparent that
the members of this class of compounds are very
effective in increasing the age-resisting properties
of rubber when incorporated therein prior to vul
canization. These compounds are equally effec
tive when incorporated in a vulcanized rubber by
any of the commonly employed methods, such as
treating the vulcanized rubber with a solution of
00
the compound.
‘
groups.
8.. Rubber having incorporated therein a small
amount of dibenzyl benzidine.
55
9. The method of increasing the age-resisting
properties of rubber which comprises incorporat
ing in the rubber a small amount of a compound
having the formula
’
While, in the above tests, we have disclosed the
employment of about 1% of the deterioration in
hibitor, it is to be understood that this amount
may be varied according to the requirements of
the rubber stock and the desire of the user.
While we have disclosed certain speci?c com
pounds and the use of certain speci?c proportions
thereof in certain speci?c processes, it is to be
.understood that the same are given merely by way
of illustration and various modi?cations thereof
will readily appear _to those skilled in the art
within the scope of our invention. Accordingly,
our invention is to be limited solely by the ap
pended claims construed as broadly as is per
missible in viewof the prior art. .
in which R and R1 represent identical aralkyl
'
.
H
H
RAPHLR.
60
in which A represents a diphenyl nucleus, R
represents a member of the group consisting of
alkyl and aralkyl groups and R1 represents a
member of the group consisting of hydrogen and
alkyl and aralkyl groups.
10. The method of increasing the age-resisting
properties of rubber which comprises incorporat
ing in the rubber a small amount of arcompound
70
having the formula
H
H
in which A represents a diphenyl nucleus, and R
and R1 each represents an aralkyl group.
175
3
2,121,618
11. The method of increasing the age-resisting
properties of rubber which comprises incorporat
ing in the rubber a small amount of a compound
having the formula
H
ing in the rubber a small amount of a compound
‘
H
|
having the formula
in which R and'R1 each represents an aralkyl
group.
in which A represents a diphenyl nucleus, and R
and R1 each represents an alkyl group.
12. The method of increasing the age-resisting
properties of rubber which comprises incorporat
ing in the rubber a small amount of a compound
having the formula
in which A represents a diphenyl nucleus, and
and R1 represent identical aralkyl groups.
13. The method of increasing the age-resisting
properties of rubber which comprises incorporat
20
15. The method of increasing the age-resist
ing properties of rubber which comprises incor
porating in the rubber a small amount of a com—
pound having the formula
H
H
in which R and R1 represent identical aralkyl
groups.
16. The method of increasing the age~resisting
properties of rubber which comprises incorporat
ing in the rubber a small amount of dibenzyl
ing in the rubber a small amount of a compound
benzidine.
having the formula
amount of N-benzyl N’-propy1 benzidine.
17. Rubber having incorporated therein a small
18. The method of increasing the age-resist
ing properties of rubber which comprises incor
25
in which A represents a diphenyl nucleus, and
R and R1 represent identical ,alkyl groups.
14. The method of increasing the age-resisting
properties of rubber which comprises incorporat
porating in the rubber a small amount 01' N~ben~
zyl N'-propy1 benzidine.
IRA WILLIAMS.
ARTHUR MORRILL NEAL.
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