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' Fireman“. 19, 1946
" 2,411,275’
UNITED STATES PATENT orrlce
Ivar H. Kinneberg and Charles L. Thomas, River-I
side, llll.,v assignors' to Universal Oil Products
Company, Chicago, 111., a corporation oi’ Dela
ware
‘ No Drawing. Application March 12, 1943,
Serial in. 478,963
21 Claims. (Cl. 260-—79)
l
I
This invention relates to a process for pro
pally conjugated dioleiinic hydrocarbons. a Under
some circumstances acetylenic hydrocarbons may
ducing rubber-like material having elastic and
' tensile properties and other desirable character
be utilized similarly although not necessarily
istics similar to those of natural rubber.
An‘ object of this invention is to produce- syn
thetic rubber-like material from ole?nic hydrol'
carbons and Other organic compounds derived
therefrom.
<
_
'
under the same conditions of operation.
Sulfur monochloride, which is generally rep
resented by the formula S2Cl2, is producible by
the action of chlorine on sulfur or of chlorine on
.
a metal sul?de. As sulfur monochloride is now a
Another object is to produce synthetic rubber
product, further‘details of its manu
like materials ‘with not only high tensile strength 10 commercial
facture are not described herein.
»
and elasticity, but with good resistance to wear,
The
reaction'of
sulfur
monochloride
with
pro
oxidation, and hydrocarbon solvents.
.
pylene results in the formation of a dichloro di
In accordance with the ' present invention a
propyl sul?de. The resultant product comprises
rubber-like material is produced having high ten
essentially beta,beta'-dichloro ‘di-n-propyl sul_
sile strength, good elasticity, and other desirable 15 fide
but may have one or more‘ of the branched
characteristics of natural rubber by a series of
‘chain structures illustrated by the following for
reactions, in which propylene or a propane-pro
pylene fraction and a diole?nic hydrocarbon,
e
mulae:
such as butadiene, are treated with sulfur mono
chloride. preferably in the presence of an alcohol
or water, and the resultant mixture of ?,B’-di
chloro dipropyl sul?de and polychloro polyalkyl
sul?de, the latter producible from the diole?nic
hydrocarbon, is treated with an aqueous solution
tion relates to a process which comprises reacting
propylene and a diole?n with sulfur monochlo
'
CH:
.
'
CH;
cl-oH§-<l:H-s—cn—orn-o1
as
I
on»
on;
Ole-(BH-O‘Hr-S-élH-ClirCl
of a water-soluble polysul?de, such as sodium 25
polysulflde, to form a rubber-like product.
One speci?c embodiment of the present inven_
>
.
The reaction between propylene and sulfur
monochloride apparently does not result in the .
formation of gamma,gamma'~dich1oro-dipropyl -
sul?de which may be referred to as gamma,
ride to form a chloroalkyl sul?de mixture and 30 gamma'fdichloro-di n-propyl sul?de having the
following structural formula: '
treating said mixture with an aqueous solution
of a water-soluble polysul?de to form a rubber
lilce material.
.
Propylene utilized as a starting material for
the process of this invention may be obtained 35 Similar reaction of a diole?n'such as buta
diene- 1,3 with sulfur monochloride results in the
from any source including the catalytic dehydra
formation of polyhalo alkyl sul?des containing
tion of a propyl alcohol, the separation of a pro
more than two chlorine atoms per molecule! This
pane-propylene fraction from cracked gases, the
reaction involving ?rst 1,4-and then 2,3-addition I
catalytic or thermal dehydrogenation of propane
of sulfur monochloride to butadiene may be illus
to propylene, etc. ' It is not to be inferred that
trated by the following equation:
1
at di?erent propylene-containing fractions
mentioned above are necessarily equivalent to
propylene of high purity resulting from catalytic
dehydration of a propyl alcohol.
I
> n
Similarly, simultaneous 1,2- and 3,4-addition
reactions are also possible‘and lead to the produc
tion of other long chain materials which may be
indicated as follows:
l
Diole?nic hydrocarbons employed in the proc
I
l
'
‘
l
I‘
|
Long and interwoven chains of carbon and sul;
ess of the present invention may be obtained from
for atoms may thus be formed, particularly wher.
any source, and comprise butadiene-1.3,isoprene,
propylene-diole?n mixture charged contains
piperylene,- and'higher boiling diole?ns, princi- 55 atherelatively
high proportion of the diole?nic ma
l
l
£411,276
may be referred to as a polyhalo
terial. in general such mixtures contain a higher
molecular proportion of propylene than of di
ole?n. Mixed reaction products may be formed
by substantially simultaneous reaction of pro-v
pylene and diole?n with sulfur monochloride.
Unexpected results are obtained by treating the
sul?de:
. and reacting said mixture with an aqueous solu
tion of an inorganic polysul?de such as sodium
polysul?de to form‘ a latex-like suspension of a
rubber-like " material.
The rubber-like -material
thus formed from propylene and butadiene (the
latter being a typical diole?n), by the reactions
propylene-diole?n-sulfur monochloride reaction‘ herein described, may consist of- long and inter
product with an ‘aqueous solution of an alkali
woven chains of carbon and sulfur atoms. The
metal polysul?de in that the rubber-like ma
structural unit of ai long chain molecule of this
terial so produced is superior to that obtainable 10, typemay be represented "by the following for
from similar treatment of dichloro dipropyl sul
l?de; the latter producible from propylene and
mula:
_
-
_
'
-
v
A
'
r
‘
‘
S:
on. f
S
on; ,
.
CH:
, s:
' CHI
I
H
B
l
-
4
n
in which n is the number of times the above
sulfur monochloride. The presence of relatively
indicated unit is present in the polymeric rub- '
small amounts of the'diolefln-sulfur monochlo
her-like material of high molecular weight. Be
ride reaction product in admixture with dichloro 25’ cause of the di?'erent possible ways in which sul
dipropyl sul?de results in the formation of a‘
fur monochloride may react with butadiene, the '
rubber-like material having greater elasticity and
following structural formulae may represent other
toughness than possessed by that formed simply
structural units which may be present in a rub
dichloro
di-propyl
sul?de
‘from condensation of
30 her-like material formed by reacting propylene
with sodium polysul?de.
_
"
.
andbutadiene with sulfur monochloride and con
The condensation of dichloro dipropyl sul?de
densing that reaction product with sodium poly
with an inorganiclpolysul?de, such as sodium
tetrasul?de, results’: in the formation of ‘a long
sul?de:
‘
‘
1
CH:
_
CH:
8
a,
s
H.
H;
L
CH!
CH]
m
H:
It is thus seen that ‘the rubber-like material
chain or linear polymer, the structural unit of
‘ formed by the present process may be of exceed
which may be represented by the following for
mula:
3" CH:
'
E111
CH:
H:
I
b
ingly complex structure; and that said structure
Clip
S
When dichloro dipropyl sul?de is condensed with
' sodium polysul?de under preferred conditions of - 65
operation which include a temperature of from
about 30 to about 120° C. andin the presence of
a dispersing agent such as freshly precipitated
magnesium ‘hydroxide, the resultant product is
a somewhat plastic rubber-like material.
In accordance with the present invention, we
propose to reduce the placticity and otherwise
improve the other rubber-like properties of the
is dependent upon the proportions of propylene
and diole?nic hydrocarbon vcharged to reaction
with sulfur monochloride, the chemical reaction
with sulfur monochloride,the chemical reactivity
and structures of the products so formed, the
nature of the water-soluble polysul?de employed;
the temperature and pressure conditions utilized
in the different steps of the process, and other
factors.
'
In accordance with the process of the present
invention, a hydrocarbon fraction containing pro
pylene and a diolefin such as butadiene, generally
above indicated reaction product by forming a
mixture of dichloro dipropyl sul?de and a diole 75in admixture. with propane and butanes, is
fin-sulfur monochloride reaction product which
2,411,275 '
treated with sulfur monochloride at a tempera
ture of from about 0° to about 150° 0., but pref
erably at a temperature of from about , 20° to
about. 60° C., under a pressure up to about 10
atmospheres in a reactor provided with good agi
tation or mixing. This reaction is generally car
ried out in the presence of a hydroxy compound
of the class ROH in which'R may be a hydrogen
‘atom or an alkyl group.
~
/
polysul?des and tetraalkyl ammonium polysul
The treatment of a mixture of dichloro di
propyl sul?de and a diole?n-sulfur monochloride
CJI reaction product with an inorganic polysul?de,
such as sodium polysul?de, is generally carried
out by slowly adding this chloroalkyl sul?de mix
' ture to an aqueous solution of the sodium poly
Such an addition of
sul?de containing a dispersing agent‘ such as
water or of an alcohol, the latter containing from
magnesium hydroxide so as to effect substan
' l to about 5 or more carbon atoms per molecule,
tially complete reaction between the dichloro di
propyl sul?de, the diole?n-sulfur monochloride
tends to promote a smooth reaction between pro
pylene, diole?n, and sulfur monochloride to form
relatively high yields of a desired chloroalkyl
reaction product, and the sodium polysul?de to
form a‘latex-like suspension of a high molecular .
sul?de mixture. ' The presence of the hydroxy 15 weight organic polysul?de. The condensation
compound also promotes the separation of sulfur
reaction with the sodium polysul?de solution is
from the reaction product formed from a pro
generally carried out at a temperature of from '
pylene-diole?n mixture undergoing reaction with
about 30° to about 120° 0.7 As the alkali metal
polysul?de is in aqueous solution and since this
water so employed is generally about 10 weight 20 solution contains a dispersing agent, the chloro
‘ per cent of the sulfur monochloride charged.
alkyl sul?de mixture is dispersed in the aqueous
The sulfur which is separable from the ole?nic
phase during this treatment and reacts to form
hydrocarbon-sulfur monochloride reaction prod
a latex-like product or suspension of an organic
uct as hereinabove set forth is generally present
polysul?de. The organic polysul?de product
therein in what may be termed a labile condition. 25 herein also referred to as a rubber and existing
It is not clear whether the labile sulfur is bound
as a latex-like suspension may be washed with
chemically in the chloroalkyl sul?de mixture or .
water by settling and decantation to remove sub
whether it is in solution. The amount of sulfur
stantially all water-soluble salts.
present in such labile condition is substantially
The resultant washed latex-like suspension
equal .to one-half of the total sulfur content de 30 which may contain upwards of 80% or better by
rived from reaction of the ole?nic hydrocarbons
weight of a rubber, may be treated with'small
and sulfur monochloride. Also, while it is some
amounts of an acid, generally a, mineral acid such
times desirable to effect separation of labile sulfur
as hydrochloric acid, in order to coagulate. the
from a chloroalkyl sul?de mixture before treat
latex-like suspension and to form a coagulum of
ing the latter with sodium polysul?de solution, 35 the‘ rubber-like material ‘which may be‘ com
it is not‘ imperative to do so in order to produce
pounded in substantially the same manner as
a polyalkyl polysul?de rubber of good quality.
‘crude rubber with reinforcing pigments such as
. The charging stock containing the propylene
carbon black, ?llers, plasticizers, and a vulcanizae
diole?n mixture is generally introduced gradually
tion agent such as ‘zinc oxide with or without
to the well stirred sulfur monochloride because 40 sulfur and cured by heat and pressure. Alterna
care is needed to prevent the reaction tempera’
tively, the latex-like ‘suspension may be com- ‘
ture from'rbecoming too high due to the exo
pounded by mixing before coagulation. The raw
thermic nature of the reaction between the un
rubber-like synthetic material, ‘produced and
' saturated hydrocarbons and sulfur monochloride.
compounded inaccordance with the process of
The hydrocarbon mixture containing propylene 45 the present invention, is suitable for use in the
and a diole?n such as butadiene is sometimes
production of tiresrand many types of mechanical
introduced at such a rate that small amounts of
goods heretofore manufactured ‘generally from
these unsaturated hydrocarbons are not absorbed
natural rubber as well as in special applications
and escape from the reaction zone.‘ The reaction
where 011 resistance not possessed by natural rub
60
product so formed from propylene, butadiene,
ber is desired. It may also be-compounded with
and sulfur monochloride may be distilled at re
natural rubber or hydrocarbon synthetic rubbers _
duced pressure to separate the desired chloro
to impart oil resistance to them.
alkyl sul?de mixture from relatively small
The latex-like dispersion obtained as herein
amounts of higher boiling materials, or the total‘ ' above set forth may also be utilized as such for
product itself may be employed in the next step 55 impregnating fabrics and other materials'or it
of the process in which this product or the dis
may be separated by means of a centrifuge into
tilled chloroalkyl sul?de mixture is treated with
a more highly concentrated latex. The latex-like
an aqueous solution of a water-‘soluble inorganic
material so obtained by centrifugation may be
sulfur monochloride.
The amount of alcohol or
polysul?de, suchas sodium polysul?de, of which
' utilized as a paint or lacquer for applying a rub
sodium. tetrasul?de with the, general formula 60 ber-like coating to metals, fabrics, and other
Nazsi, is representative. Suitable polysul?des of
sodium‘ have the general formula NazSn in which
n is an integer of 2 to about 5, inclusive.
‘
Although sodium polysul?de is the water-sol
uble polysul?de generally‘ employed for treating 65
the above mentioned chloroalkyl sul?de mixtures
to form ‘rubber-like materials, other inorganic
polysul?des utilizable similarly, although not
necessarily under the same conditions of oper
ation, include alkaline earth p'olysul?des and par
ticularly calcium polysul?des of the general for
mula Case or potassium polysul?des of the gen
eral' formula KzSn wherein n may vary from 2
to about 5, inclusive, vand polysul?des of basic
nitrogen compounds, particularly ammonium
.
materials.
,
'
" The following results are given to illustrate the
‘process of the invention, although with no inten
tion of unduly limiting. its generally broad scope.’
When 17 grams of substantially pure 1,3-buta
diene was vaporized into a bubbler containing 42
grams of sulfur monochloride at room tempera- .
ture, the reaction mixture becomes hot, darkened
in color,’ and hydrogen chloride was evolved. The
reaction mixture also became so viscous that no
more butadiene couldvbe introduced thereto by
the method employed.
'
.
~
-
_
_ g
In another run, substantially pure- 1,3-buta
diene, dried by passage through calcium chloride,
was passed at a rate of about 2.5 cubic feet per
2,411,275
,
_
,
g;
\,
obtained was dried by working in a warm mill
hour through a bubbler containing-methanol at
0° C. The resultant mixture of 1,3-butadiene and
methanol vapors was then reacted with 375 grams
of well agitated‘ sulfur monochloride contained
whereby a brown rough sheeted material was ob
tained which resembled soft gum rubber. The
brown sheeted'material was suitable for com
in a reactor cooled by a water-bath so that the 5- pounding with reinforcing and vulcanizing agents
reaction temperature was not permitted to exceed
such as carbon black and zinc oxide, respectively.
35° C. The sulfur monochloride was thus con-
The character of thepresent invention and
. verted into reaction products over a period of_
‘type of results obtained are evident from the
about 4 hours during which about 6.5 grams of
preceding speci?cation and example, although
methanol was vaporized. Within 2. hours after .10 they are not- to be considered as imposing undue
the start of the experiment, the reaction product
limitations upon its'generally broad scope.
had become so viscous as to require the addition
We claim as our invention:
thereto of 320 grams of carbon tetrachloride _
diluent. The reaction product dissolved com-
'
'
'1. A process which comprises reacting propyl
ene and a conjugated diole?n with sulfur mono
pletely in the'carbon tetrachloride forming a light 15 chloride to form a mixture of chloroalkyl sul?des
, brown colored solution with no deposition of sulfur or loss of hydrogen chloride. This yield of
and treating said mixture with an aqueous solu- ’
tion of awater-soluble polysul?de. Y
,
‘
butadiene-sulfur monochloride reaction product .
2. A process for producing an elastomer which
was 98% of the theoretical based upon the sulfur
comprises reacting propylene and a conjugated monochloride which reacted with an equimolec‘ue 2o diole?n withv sulfur monochloride to form a mix- _
' lar quantity of butadiene.
ture of chloroalkyl sul?des, treating said mixture'
In a third run, sulfur monochloride was simiwith an aqueous solution of a water-soluble poly
larly reacted with a mixture containing '73 mole
per cent of propylene, 3.0% propane‘, 1.1% ,butyl-
‘sul?de in the presence of a dispersing agent to
form a dispersion of organic polysul?des, washing =
enes, 22.1% 1,3-butadiene, and 0.8% ‘pentanes and 25 said dispersion with water until substantially free
higher hydrocarbons. This gas mixture which
from water-soluble salts, and treating the washed
was dried by_calcium chloride was passed at a
dispersion with an acid to form a coagulum.
. rate of '2 cubic feet, per hour through a bubbler
' 3. A process for producing an elastomer which
containing methanol at 10° C. and was then introcomprises reacting propylene and a conjugated
duced to a reactor containing 382 grams of sulfur 30 diole?n with sulfur monochloride in the presence
monochloride which was rapidly agitated and
of ‘a hydroxy compound selected from the group
maintained at a temperature of from 45 to 50° C.
consisting of a monohydric alcohol and water to
A total of 24.2 grams of methanol was- so intro-
form a mixture of chloroalkyl sul?des and treating
duced with the propylene-butadiene mixture
charged.
'
said mixture with anaqueous solution of a. water
35 soluble polysul?de.
The *reaction appeared to be complete in about
"
4. A process for producing an elastomer'which
3'hours'but the charging of the propylene-buta-
comprises reacting propylene and a conjugated
diene mixture was continued for a total time of
diole?n with sulfur monochloride in-the presence 1
4.5 hourg in order to insure complete reaction
of a hydroxy compound selected from the group
of all of the sulfur monochloride. The reaction 40 consisting of a, mgnohydric alcqhol and water to
form a mixture of chloroalkyl sul?des, treating
product was a clear oily amber colored liquid with
a density of 1.25 at 20° C. There was no loss of
said mixture with an aqueous solution of a water
reaction product was 599 grams which corre
soluble polysul?de in the presence of a dispersing
agent to form a dispersion of organic polysul
45 ?des, washing said dispersion with water until
sponded to 98% of the theoretical upon the basis
' substantially free from water-soluble salts, treat—
hydrogen chloride from the reaction product and
it contained no precipitated sulfur. The yield of
of the quantity of sulfur monochloride charged
ing the washed dispersion with an 'acid to form a
together with the assumption that 2 molecular ‘
- proportions of sulfur monochloride reacted with
‘coagulum, and subjecting said coagulum to drying
1 molecular proportion of butadiene plus 2 molec
ular proportions of propylene. This clear, amber
colored liquid was substantially saturated as evi
denced by a bromine number of 3.7.
50
treatment.
5.‘ A process for producing an elastomer which
comprises reacting propylene‘ and butadiene 1,3 .
with sulfur monochloride at a temperature of
' from about 0° to about _150° C. to form a mixture -
The product so obtained from propylene, buta
of chloroalkyl sul?des, treating said mixture with
diene, and sulfur monochloride was reacted with 55 an aqueous solution of a water-soluble‘ polysul?de
an aqueous sodium tetrasul?de solution prepared
at a temperature of from about 30° to about 120°
by dissolving technical sodium sul?de with sulfur
C. in the presence of a dispersing agent to form a
in boiling water. In this condensation treatment
dispersion of organic polysul?des, washing said
0.43 molecular proportion ('72 cc.) of the propyl 60 dispersion with water until substantially free from
ene-butadiene-sulfur monochloride reaction prod
water-soluble salts, and treating the washed dis
uct ‘(without further puri?cation) was added
. persion with an acid to form a’coagulum.
\
slowly with vvigorous stirring to 0.5 molecular
'6. A process for producing an elastomer which
proportion (2'75 cc.) of the aqueous sodium tetra
comprises reacting‘propylene anda conjugated
sul?de solution containing approximately 5 grams 65 diole?n with sulfur monochloride in the presence
of freshly precipitated magnesium hydroxide em
'ployed as a dispersing agent.- The condensation . of a hydroxy compound‘selected from the‘ group
consisting of a monohydric alcohol and water to
took place at 60° to 85° C. over a period of 6 hours
form
a mixture of chloroalkyl sul?des, treating
with a ‘practically quantitative yield of product
said
mixture
with an aqueous solution of a water
which was obtained as a ?nely divided and slowly _
settling suspension. This suspension of reaction 70 soluble polysul?de in the presence of a dispersing
agent to form a dispersion of ‘organic polysul?des,
product was washed by decantation with tap.
washing said dispersion with water until substan
water until substantially free, from soluble salts.
tially free from water-soluble salts, treating the
The resultant washed suspension, which was pale
washed dispersion with an acid to form a coagu
yellow in color, was coagulated by acidi?cation
with dilute hydrochloric acid. The coagulum so 75 111m, and subjecting said coagulum to drying, com
2,411,275
'-
pounding,‘ and curing treatments to produce the
elastomer,
'
.
'
'7. A process for producing an elastomer which
-
a mixture of chloroalkyl sul?des, treating said
comprises reacting propylene and butadiene 1,3
mixture with an aqueous solution of a polysul?de
of an alkali metal in the presence or. a dispersing
with sulfur monochloride in the presence of a hy
droxy compound selected from the group consist
ing of a monohydric alcohol and water to form
agent comprising magnesium hydroxide to form
a dispersion of organic polysul?des, washing said
a mixture of chloroalkyl sul?des, treating said
dispersion with water until substantially free
from water-soluble salts, treating the washed dis
mixture with an aqueous solution of a water-solu- -
ble polysul?de inthe presence of a dispersing
10 persion with an acid to form a coagulum, and
. agent to form a dispersion of organic polysul?des,
subjecting said coagulum to drying, compound
ing, and curing treatments to produce the elas
washing said dispersion with water until substan
tially free from water-soluble salts, treating the
tomer.
washed dispersion with an acid to form a coagu
lum, and subjecting said coagulum to drying, com-v
pounding, and curing treatments to produce the
l0
hydroxy compound selected from the group con
sisting of a monohydric alcohol and water to form
'
13. A process for producing an elastomer which
15
elastomer. '
8. A process for producing an elastomer which
comprises reacting propylene and butadi‘ene 1,3
with sulfur monochloride in the presence of a hy
droxy compound selected from the group consist
ing of a monohydric alcohol and water to form
a mixture of chloroalkyl sul?des, treating said
with sulfur monochloride at a temperature of 20 mixture with an aqueous solutionof sodium poly
from about 0° to about 150° C. in the presence of a
sul?de in the presence of a dispersing agent to
hydroxy compound selectedfrom the group con
form a dispersion of organic polysul?des, wash
comprises reacting propylene and butadiene 1,3
sisting of a monohydric alcohol and water to form
a mixture‘ of chloroalkyl sul?des, treating said
mixture with an aqueous solution of a water-solu
ble polysul?de at a temperature of from about 30°
to about 120° C. in the presence of a dispersing ‘
agent comprising magnesium hydroxide to form a
ing said dispersion with water until substantially ’
free from water-soluble salts, treating the
washed dispersion with an acid to form a rubber
like coagulum, and subjecting said coagulum to
drying and curing treatments to produce the
(elastomer.
-
'
-
dispersion of organic polysul?des, washing said
dispersion with water until substantially free from
water-soluble salts, treating the washed dispersion
14. A ‘process for producing an elastomer
30 which comprises‘ reacting propylene and bu
tadiene 1,3 with sulfur monochloride at a tem
with an acid to form a coagulum, and subjecting
perature of from about 0° to about 150° C. in the
said coagulum to drying to produce the elastomer.
presence 01’ a hydroxy compound selected from
9. A process which comprises reacting propyl
the group consisting of a monohydric alcohol and
ene and a conjugated diole?n with sulfur mono-' - water to form a mixture of chloroalkyl sul?des,
chloride to form a mixture of chloroalkyl sul?des
treating said mixture with an aqueous solution
and treating said mixture with an aqueous solu
of sodium polysul?de at a temperature of from
tion of a polysul?de of an alkali metal. '
about 30° to about 120° C. in the presence of ‘a
10. ‘A process‘ for producing an elastomer
dispersing agent comprising magnesium hy
which comprises reacting propylene and a con‘ 40 droxide to form a dispersion of an organic poly
jugated diole?n with sulfur monochloride inv the
sul?de, washing said dispersion with water until
presence of a hydroxy compound selected from
substantially free from water-soluble salts, treat?
the group conslstingof a monohydric alcohol and
ing said washed dispersion with an acid to form
water to form a mixture of chloroalkyl sul?des,
a coagulum, and subjecting said coagulum to
treating said mixture with an aqueous solution of 45 drying, compounding, and curing treatments to
a polysul?de of an alkali metal in the presence of
produce the elastomer.
a‘dispersing agent to form a dispersion of organic
15. A process which comprises reacting pro
polysul?des, washing said dispersion with water
pylene and a conjugated diole?n with sulfur
until substantially free from water-soluble salts,
monochloride to form a mixture of chloroalkyl
treating the washed dispersion with an acid to 50 sulfides and treating said mixture with an aque
form a coagulum, and subjecting said coagulum
ous solution or a polysul?de or an alkaline earth
to drying, compounding, and curing treatments
to produce the elastomer.
,
11. A process for producing an elastomer which
comprises reacting propylene and butadiene 1,3 '
with sulfur monochloride in the presence of a
metal.
'
‘
16. The process of claim 4 further character
ized in that said water-soluble polysul?de com
prises a polysul?de of an alkali metal.
sisting of a monohydric alcohol and water to form
17. The process of claim {further character
ized in that said wateré-soluble polysul?de com
prises a polysul?de of an alkaline earth metal.
a mixture of chloroalkyl sul?des, treating said‘ '
mixture with an aqueous solution of a polysul?de
claim 4.
‘hydroxy compound selected from the group con- -
of an alkali metal in the presence ‘of a dispersing
agent to form a dispersion of organic polysul?des,
washing said dispersion with water until substan
tially i'ree fromwater-soluble salts, treating the
washed dispersion with an acid to form a coagu
lum, and subjecting said coagulum to drying,
compounding-and curing treatments to produce
the elastomer.
.
12. A process for producing an elastomer which
18. An elastomer formed by the process of
claim 8.
'
20. The process de?ned in claim 1 further
characterized in that the water-soluble polysul
,?de comprises a polysull?de of an alkali metal.
21. The process de?ned in claim 1 further
characterized in that the water-soluble polysul
?de comprises a polysul?de of an alkaline earth
comprises reacting propylene and butadiene 1,3 70 metal.
with sulfur monochloride in the presence 01' a
v
19. An elastomer formed by the process of
IVAR H. KINNEBERG.
CHARLES L. THOMAS.
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