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Патент USA US2370253

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Patented Feb. 27, 1945
I 2,370,253
UNITED STATES PATENT‘ OFFICE
2,370,253
ARYLENE THIAZYL ,SULPHENAMIDES
William E. Messer, Cheshire, Conn., assignor to
United‘ States Rubber Company, New York,
N. Y., a corporation of New Jersey
No Drawing. Original applications June 24, 1939,
_Serial No. 280,929, and May 10, 1940, Serial No.
334,343. Divided and this application Septem
ber 18, 1942, Serial No. 458,860
'
,
3 Claims. ( CI. 260-30613)
chloride and aniline ('N-phenyl benzothiazy1sul
phenamide).
This invention relates to a new class of com
pounds which have been found valuable as accel~
erators for the vulcanization of rubber.
This case is a division of my copending appli
‘cations Serial No. 280,929, ?led June 24, 1939,
Patent 2,321,305, and Serial No. 334,343, ?led May
10, 1940, Patent 2,321,306.
The new class of chemicals may be represented '
by the general formula
66 grams crude 1,1’ dithio bis benzothiazole are
stirred with 300 to 600 cc.- carbon tetrachloride
and‘ dry chlorine passed in until complete solu
tion ensues and about 14.1 grams of chlorine has
been absorbed. About 70 cos. of aniline are then
16 added with stirring and after standing a short
,where AR is an arylene group.
while the resulting. solution is filtered and the
The materials are derivatives of arylene-thiazyl
precipitate washed with a little carbon tetra
sulphur chloride, wherein the chlorine is replaced
chloride, recovering some 47 grams pure aniline
by the
hydrochloride (aniline salt). The carbon tetra
20 chloride ?ltrates are evaporated to dryness (con
radical above, when one mole of the arylene
thiazyl sulphur chloride is reacted ‘with one mole
of a primary arylamine, such as aniline, naph
thylamine, alpha, naphthylamine, beta naphthyl
amine, etc. During such reaction‘ hydrogen chlo
ride is eliminated.
densing and recovering carbon‘ tetrachloride
used) leaving 105 grams of dark gray, oily crys
tals. These may be puri?ed by washing with
alcohol and drying, thereby obtaining 60 grams of
25 light gray colored crystals, melting at 119-122°'C.
\ In the following illustrative example, benzo
66 grams of pure 1,1’ dithio bis benzothiazole
thiazyl sulphur chloride is used as the reagent;
it may be prepared in solution, for purposes of 30 (made by recrystallizing the product used in A
from benzene) are treated in the same way as in
reaction by passing dry chlorine into a slurry of
1,1’ dithio bis benzothiazole in benzene, carbon
tetrachloride, etc.
A.
‘52.7 grams pure aniline salt are recovered.
guanidine, thiuram sulphides such as tetramethyl
thiuram monosulphide, etc., which have the ac 40
tion of activating the accelerating ability of
ized and tested.
97.5 grams‘of crude N-phenyl benzothiazyl sul
phenamide of melting point 114-118“ C. are ob
The materials are delayed-action accelerators
similar in this respect to 1,1’ dithio bis benzo 35 tained and this will yield 75.3 grams N-phenyl
benzothiazyl sulphenarnide melting point 118
thiazole itself. They may be used alone or in
120° C. on puri?cation.
conjunction with basic nitrogen compounds such
The following rubber mixes were made, vulcan
as ammonia, amines, guanidines such as diphenyl
-
I
Stock
thiazole accelerators. They may also, if desired,
be used in admixture with other thiazole accel
erators such as the mercapto-ibenzothiazyl sul
phides.
The following example is given to illustrate
the invention in which comparison is made with
a stock containing 1,1’ dithio bis benzothiazole
(parts are by Weight) :
1
46
Pale crepe ________________ ._
Zinc oxide... . .
Lithopone_.___
Whiting ______________________________ .
Suprex clay _________________ __
,
Zinc soap of cocoanut oil so
Sulphur ____________________ __
EXAMPLE
The reaction product of benzothiazyl sulphur
50 1,1’ dithio bis benzothiazole-_.._
N-phenyl benzothiazyl sulfenamide .............. __
,_.
posh-$0 maukWHhOIlQg
mu-1o
H
2
Tensiles-Unayed
A
B
Minutes cure at 30 lbs/sq. in steam
'
pressure
'1‘
E
953
T
2,370353
_
other well known ?llers, pigments and the like
may be employed in the production 01' various
types of rubber compounds as will be apparent
to those skilled in the art to which this invention
pertains.
E
300
843
513
460
, 666
546
626
1, 160
1,860
673
563
596
2,160
636
Search test
AS
A
B
[5 where AR is an arylene hydrocarbon group.
Minutes cure at 5 lbs.lsq. in steam
pressure
\
Having thus described my invention, what I
claim and desire to protect by Letters Patent is:
1. A compound having the general formula
2. A N-monoaryl monobenzothiazyl sulphen
‘
amide‘having the general formula
130
137
155
192
132
1, 330
1, 515
1, 445
1, 337
l, 050
200
203
210
215
225
305
855
652
577
247
275
1, 437
1,280
1, 243
1, 197
II 107
852
810
3. A compound having the general formula
T=Ultimate tensiles in pounds per square inch.
E=% elongation at break.
The term “rubber” herein is to be understood
as including caoutchouo and similar vulcanizable
gums, natural or synthetic, including latices
thereof.
Other ratios of the compounding ingredients 30
than those mentioned in the example as well as
N
/
\
\s
WILLIAM E. MESSER.
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