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Патент USA US2133779

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Patented Oct. 18, 1938
2,133,779:
‘UNITED ‘STATES PAT ENT
; 2,133,779
"
'
PRESERVING RUBBER
Ohio, assi'gnor-to Wing
foot Corporation, Wilmington, Del., a, corpora;
tiqn of Delaware
'No Drawing. Application May- 5, 1936,
Serial No. 78,007 .
'13 Claims.
This invention relates to thetreatment of rub
ber. More particularly it relates to a method of
retarding the deterioration of rubber due .to
aging. This case is a continuation in part of
application Serial N0.>618,087 ?led June 18, 1932.
Many compounds have been suggested for use in
rubber as antioxidants and ag'e-resisters. By
the present invention it has been'discovered that
still another class of materials is suitable for this
purpose. These new antioxidants may be repre
only-0H2
vIQ
sented by the formula R1—0——R—NH2, in which
R is an alkylene group and R1 is an aryl group.
CO
This aryl group R1 may contain various sub
stituent groups, including amino groups, the above
15 formula representing, in a general manner, the
compounds falling within the scope of the in-
V
p
vention and embracing specieshaving substituen'ts
20
7
onFollowing
the ring. are the formulae of some representative compounds:
2' 5.
.O-—CH2—-CH2-—NH2
.
2:5
‘
c
,
OHO
7
‘
_
.
/ CH3
l
,7
.
~
.
V
'
»
I>
-.
t~'
'
'
—-O‘—<OHa—-CI§H—~CHz--NH2
OH
I
.
I
'
.
'
25.
(fHa
CHa-NH
t CH3
o-om-NH,
~
.
9
CFCH’CHFNH
O_CH3
35
'
O_CH?_.ZH_CVHE_NHQ
H
.O-—CHz—OHz-CHn-—NH2
30
.
'
V
7
CHa
,
p
v‘
O-CHr-QHrNH'z
—O-——OHz-—CHz-CH¢~CH2—NH2 '
O—C.Hz-—,?H—NH2
C2Ha
HO”
c v
7
' ‘
l"
I
v
'
'
l'l'
40
_
0-NH:
H-OHa
HO®—NH®—0—CHz—CH—OHz-NH2
'
(‘>11
40
QNHQO—QHT~CHT—NH1
45
cH.C>-NHONH®_0-om—_cm—NH,
CH3
45
.
O—OH:—CHa—-NH:
NH——-CH:—CHz—-NH
HO’
O~CHr~CHr-NH2 50
2,133,779
2
'
0-01; on NH
O '- r \O
...................... ..HN
-0-CH:-CH:-NH
O-CHr-CHz-NH---------.--
__.._-___._-_
of the samples before and after aging and by the
low increase in weight shown, this latter being
due to the oxygen absorbed during aging.
Although only the preferred forms of the inven
tion have been described in detail, it will be ap 10
10 nally stated.
The type of compound herein described for use parent to those skilled in the art that various
may be made therein without de
in rubber has been mentioned in the literature modi?cations
parting from the spirit of the invention or the
and methods of preparation set forth. For ex
of the appended claims, in which it is
ample, in Beilstein, 3rd ed. (1896), Vol. II, page scope
intended
that the patent shall cover by suitable 15
15 877, aminoethyl naphthyl ether is described and expression in such claims, all features of patent
the statement made that the compound may be
prepared by heating bromethyl naphthyl ether able novelty residing in the invention.
I claim:
7
with an alcoholic solution of ammonia at 100° C.
1. The method of treating rubber which com
The product is a white amorphous material. In-‘ prises incorporating therein an age-resister hav 20
stead of the bromo-compound, other correspond
ing halogen compounds, such as chlorethyl ing the formula R1——O—-R—-NH2, in which R is
and R1 is aryl.
naphthyl ether, may be employed if desired. The alkylene
2. The method of treating rubber which com
reaction is preferably carried out under pressure prises incorporating therein beta-aminoethyl
The foregoing compounds are but a few of
those comprised by the invention and are, thus
merely indicative of the variations possible while
still conforming to the general formula as origi
in an autoclave.
Other compounds coming within the purview of
the invention may be prepared in this same man
ner, or by other methods. In fact, any method
of preparation may be followed which gives com
pounds of the character herein described and the
invention is not limited by such methods of prep
3. The method of treating rubber which com
prises incorporating therein a primary amino
alkyl phenyl ether.
.4. The method of. treating rubber which com
prises incorporating therein a primary amino
alkyl naphthyl ether.
aration.
.
The compounds may be employed with success
in most of the usual compounding formulae. The
following formula is one in which they have been
found by test to yield excellent results:
Parts by weight
,
30
.
5. The method of treating rubber which com
prises incorporating therein an age-resister hav
ing the formula R1——O_—R-—NH2, in which R is
alkylene and R1 is aryl and vulcanizing the same.
6. The method of treating rubber which com
prises incorporating therein beta-aminoethyl
The e?iciency of these compounds is admirably
illustrated by the action of beta-amino ethyl
beta-naphthyl ether and vulcanizing the same.
'7. The method of treating rubber which com
prises incorporating therein a primary amino 40
alkyl phenyl ether and vulcanizing the same.
8. The method of treating rubber which com
prises incorporating therein a primary amino~
alkyl naphthyl ether and vulcanizing the same.
9. A rubber product in which has been incor
beta-naphthyl ether. This material was incor
porated into rubber in accordance with the above
porated an age-resister having the formula
R1—0—R-—NH2, in which R is alkylene and R1 is
formula and samples were cured._ These samples
were tested before aging and after six days
aryl.
Rubber (extracted pale crepe) _________ __ 100
Zinc oxide ____________________________ __
5
Sulfur_
3
____
'
____ __
_._
Hexamethylene tetramine ______________ __
Stearic acid ___________________________ __
1
1.5
' Antioxidant ___________________________ __
45
25
beta-naphthyl ether.
. aging in an oxygen bomb.
1
The following results
10. A rubber product in which has been incor
porated beta-amino-ethyl-beta-naphthyl ether.
11. A rubber product in which has been incor
50 were obtained:
porated a primary aminoalkyl phenyl ether.
Original
Aged 6 days 01 bomb
12. A rubber product in which has been incor
porated a primary aminoalkyl naphthyl ether.
Cure
,
Tens. Elong. 500 700 Tens. Elong. 500 700
55
ilifcmsv‘?‘
35/285...
128
885
15
45
123
870
15
44
Lostwt.
5o _____ _.
7o _____ ..
14s
170
s55
800
18
25
58
93
138
11s
810
71s
19
29
70
108
.35
Lost wt.
The antioxidant qualities of the material are in
dicated by a comparison of the tensile strength
13. The method of treating rubber which com
prises incorporating therein an age resister hav
ing the formula R'—-O-—R.-—NH2 in which R is
alkylene and R’ is anaromatic radical selected
from the group consisting of phenyl and naphthyl
groups.
ALBERT M. CLIFFORD.
53
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