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Патент USA US2106465

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Patented 14.11.25, 1938
]. 2,106,465
‘UNITED STATES’ PATENT OFFICE’
2,106,465
MnncAP'ro-Tnmzonn DERIVATIVES
Ludwig Orthner', Frankfort-on-the-Main, and >_
Ewald Zaucker, Cologne-Mulheim, Germany,
assignors to I. G. Farbenindustrle Aktienge
sellschaft, Frankfort-on-the-Main, Germany
No Drawing, ' Original application June 23, 1931,
Serial No. 546,418. Divided and this applica
tion August "I, 1935, Serial No. 35,064. In Ger
‘
'
_
many June 30, 1930
&
2 Claims. ' (Cl. 260-44)
The present invention relates to new mercapto
arylene thiazole derivatives.
dichloroacetyl-dibutylamide: I
v
.
Mercapto arylene thiazoles have already been
suggested for accelerating vulcanization. This
'
5 class of substances. possesses, however, the dis
CHCIZ.CO.N(C4HI)2;
dichloroacetyl-dibenzylamide:
’
5
_ advantage of an unfavorable critical tempera
ture, that is to say, the use thereof involvesv the
danger of scorching.
\
_
CHC12.CO.N(CH2.CcHs) a;
'
It is applicants’ invention to have found new
mercapto arylene thiazole derivatives which are
as.dichloroacetyl-phenylhydrazide: ‘
characterized by a substantially higher critical
temperature when applied in vulcanization proc
CHC12.C)0.NH.NH.CcH5;
ess. The new compounds are acetamides in
which at the most 2 hydrogen atoms of the methyl
15 group linked to the C0 are replaced by the group
I
‘
10
as.dichloro-aceto-ortho-nitrophenylhydrazide:
CHCI2.CO.N'H.NH.CsH4.NOa;
'
l
15
dichloro-acetylpropylamide: CHC12.CO.NH.C3H7.
' The new compounds are generally colorless to
yellowish colored crystalline substances, insoluble
in water, soluble in the usual organic solvents, 20'
wherein R. stands for a benzene or naphthalene and are particularly valuable in view of their»
radical. As examples for substituents in the said - favorable critical temperatures, when applied in
benzene- or naphthalene nuclei there may be the vulcanization of rubber or of arti?cial rubber
25 mentioned alkyl, alkoxy or nitro groups or halogen like masses.
'
25
atoms.
Fonvulcanization purposes the vnew compounds
are incorporated within the rubber (which term is
These new compounds are obtainable by caus
ing an about molecular quantity of a mono- or intended to include natural rubber as well as
dihalogen acetamide to react upon about one
arti?cial rubber-like masses, derived for example,
30 molecular proportion of a mercaptoarylenev ‘from butadiene, isoprene, dimethylbutadiene or 30
thiazole or a salt thereof per each halogen atom. > another homologue or an analogue of butadiene)
As suitable halogenated acetamides there may ' in anydesired manner, for example, by rolling
be mentioned, for instance, dichloroacet-amide:
35 CHCI2.CO.NH2; N-dlchloro-acet-piperidide:
or kneading.
Obviously, a vulcanizing agent, ,
such as sulfur, agents'being capable of splitting
o? sulfur, selenium etc., is likewise added, and, 35
'if desired, other ingredients known to favorably
in?uence rubber vulcanization processes or the
CH2;
40
l. is
dichloro-acet-anilidez' CHC12.CO.NH.COH5; N-di-.
45 chloro-acetyl-anthranilic acid ester:
properties of the vulcanizates. The rubber mix
is then vulcanized in the usual manner by heat
ing it to a temperature su?icient to perform vul- 40
. canization, for example, to a temperature between
about 100-170" C.
Representatives possessing too low a velocity on
hot vulcanization, can be adjusted to give more
favorable times of heating by combination with 45
CHCh.CO.NI-I.CuH4.COOC2I-Is; >
dichloroacetyl-dimethylamide :
CHCI:.CO.N(CH;)2;
stearic acid and/or with other appropriate ac
' celerators, especially basic accelerators, while
- preserving a satisfactory critical temperature.
The following examples will illustrate the in
vention, without, however, restricting it theretoz- I
9,108,465
2 ,
Example 1
vWith a mixture of the composition:--
100 grams of llmercapto benzothlazole are
boiled with 24 grams of sodium hydroxide in 200
cos. of methyl alcohol and 38,4 grams of vdi
chloroacetamide for 5 hours; and then precipi
tated with water. After recrystallization from
propyl alcohol the reaction product obtained has
10
the melting point of 179° C. The reaction prob
ably proceeds according to the equation:—
y
'
7
Parts by weight
Crepe-
‘
Zing mrirln
100
' ‘
5
Sulfur
-
3
Stearic acid
1.5
and
The reaction product from mercapto
'
benzothiazole (sodium salt)
plus
10
with _di- -
chloroacetamide ___________________ __
0. 33
.
Diphenylguanidine (III) ______________ __
0.67
the following?gures were obtained:—
Heating
20
Example 2
In comparison with mercapto benzothlazole (I) ,
25
the condensation products from mercapto benzo
thiazole (sodium salt) , and dichloroacetamide (II)
were tested as accelerators in the following mix
ture:—
~
'
30
Parts by weight
Zinc
__
oxide
____
' '
‘
100
a
5
Sulfur _____ _.. ______________ _.'. ____ __.____
3
Stearic acid..______..__.._._____.._____-___..
Accelerator
1.5
1'
Pressure
nb. atm.
Min
utes
0.5
3.0
3.0
3.0
30
15
35
III
A
B
232
242
235
820
740
720
20
This is a division of our application for Letters
Patent Serial No. 546,418, ?led June 23, 1931.
We claim:--
1. As new compounds acetamides in which at 30
’
Crepe _____ __
‘
the most 2 hydrogen atoms of the methyl group
linked to the C0 are replaced by the group
35
The following values were obtained:-—
A=tensile strength in kg. per Sq- 0111-,
wherein R stands for a benzene or naphthalene
radical, these compounds being valuable vulca- V
B=stretch in percent.
nization accelerators;
.
40
Heating
Pressure
45
40
~
2. The product of the formula
ab.atm.
Mln-
utea
I
A
'
11
B
A
45
B
having a‘ melting point of 179° C. and being a
5
140,
~ 175}
valuable vulcanization accelerator.
.
'LUDWIG
ORTHNER.
EWALD ZAUCKER.
60
50
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