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Patentedv Dec, 3, ‘1946
‘ Frank J. Soday, Baton‘ Rouge, La., assignor to‘
The United Gas Improvement Company, a cor
poration of Pennsylvania '
No Drawing.
‘Application February 12, 1944-,
Serial No. 522,091
Y -
10 Claims. (01. 260-46)
The excellent results obtained. when esters of
.the type described herein are used as plasticizing
and/or softening agents for natural and/or syn
thetic rubber are largely due to the pronounced
solubility characteristics of such esters, and their
More particularly, this invention pertains to
excellent compatibility with natural and/ or syn
rubber compositions comprising a mixture of one
thetic rubbers and elastomers. Thisenables each
-or more natural and/or synthetic rubbers or
mill to operate at maximum throughput, with a
elastomers, and one or more esters of indene-type
very substantial saving in power.
alcohols, either alone or in combination with
The use of such esters in natural and/or syn
other softening and/or plasticizing agents.
thetic rubber compounding results in the produc
An object of the invention is to provide natural
This ‘invention relates to new compositions of
matter ‘comprising natural and/or synthetic rub- _
her and one or more ‘esters of indene-type
' tion of uniform compounds and ?nished articles
and/or synthetic rubber compositions suitable for
remarkably free'from bleeding, blooming, lea?ng,
use as tire or tube stocks; for molding and ex-'
truding purposes, for the fabrication of printers
or lamination.
In addition the low viscosity characteristics of
, esters of the type described greatly assists in the
rolls, hose, sheets, tubes, gaskets, and other ob
vjects and specialties; for the preparation of ad;
milling and blending operations, and insures rapid
and complete penetration.“ Uniform stocks pos
sessing good calendering and extruding charac
hesives and cements; and for coating, impreg
nating, waterproofing, and other specialized uses;
comprising one or more natural and/or synthetic
rubbers and/0r elastomers and one or more esters 20 teristics are thus obtained.
Esters of the type described are quite stable and
of indene-type alcohols with or without-the in
strongly resistant to thermal decomposition, thus
corporation of other additives selected from a
insuring the production of uniform compounds
list comprising sulfur, accelerators, pigments,"
resins, antioxidants, ?llers,. extenders, and/or
other plasticizing and/or softening agents, such
and finished articles free from decomposition
products. Such compounds, and the ?nished ar
ticles prepared therefrom, possess very good aging
as stearic acid, pine oil ‘and pine tar. ,Another
object of the invention is the use of esters of
_ These esters also contain substantially no free
indene-type alcohols- in conjunction‘ with other
carbon or other extraneous materials. This is of
ingredients, such as resins, resinous materials,
plastic products, and dibutyl phthalate, tricresyl 30 considerable importance from the standpoint of
phosphate, or other high boiling compounds,‘ as
~ the preparation of clean, uniform rubber com
softening and/or plasticizing agents for natural
and/or synthetic rubber. Other objects and ad
pounds and ?nished articles and from the stand
point of smooth, trouble-free mill operation.
' By a choice of the proper compounding ingre
vantages of the invention will be apparent to
those familiar with the art upon an inspection of :
dients and reaction conditions, rubber composi
tions possessing almost any desired property may
be obtained readily. Thus, products ranging from
A considerable number of the softening and/ or
‘very soft, mildly cured types to the so-called
plasticizing agents employed in rubber com
hard rubbers may be obtained at will.
pounds, .and particularly synthetic rubber com
Esters of the type desired may be regarded as
pounds, at the present time suffer from many 40
derivatives of alcohols having the following
disadvantages, among which is their lack of com
the speci?cation and claims.
structural formula
patibility with natural and, more particularly,
,with synthetic'rubber.
This lack of compatibility ‘
renders it extremely difficult to obtain a uniform
mixture or dispersion of the softener in the rub 45
ber compound, resulting in the production of non
uniform objects or products. In addition, the use
of such softening agents frequently results in the
lea?ng or lamination . of the- rubber compound
during the mastication or calendering process.
softeners in rubber compounds results in the pro
duction of ?nished objects which frequently ex-v
hibit bleeding or blooming during use.
to give esters which are unusually stable, light in
tening agents for natural and/or synthetic rub
Particularly desirable results are obtained '
rubber compositions.
ethyl, propyl, butyl, and amyl; or the like. ~ Alco
hols of this type are readily esteri?ed with acids '
I have discovered that the esters of indene-type
when such esters are incorporated in synthetic
hydrogen; and R1, R2, R3,‘R4, R5, R6, R1, and Rs
each represent hydrogen; alkyl such as methyl,
- alcohols are unusually welladapted for use as sof
in which oneof the group consisting of a and b is an hydroxyl group, the other of said group being
Finally, the incorporation of such incompatible
color, and possess exceptionally desirable odors.
- Acids which may be reacted with alcohols of
60 the type described include aliphatic monobasic'
2,411,943 "
mentioned sodium acetate, potassium acetate, cal
acids, such as formic, acetic, propionic, butyric,
cium acetate, iron acetate, lead acetate and'oth'er
valeric, caproic, oenanthic, caprylic, pelargonic,.
capric, and similar acids having a higher number
of carbon atoms, unsaturated acids, such as
The esteri?cation reaction may be carried out
in the presence or a solvent, such as for exam
acrylic acid, crotonic acid, isocrotonlc acid, meth
acrylic acid, vinylacetic acid, and the'like; halo
ple, benzene, if desired.
' ‘
monochloroacetic acid, dichloroacetic acid, al
Any suitable reaction temperature may be employed, such as forexample, the boiling point of
pha-chloropropionic acid,‘and.the like; hydroxy
the solution.
genated fatty acids, such as chloroformic acid,
at atmospheric, subatmospheric, or superatmos-r- ,
' hydroxybutyric acid, and the like; amino acids,
pheric pressures, as desiredal »
The use of a system whereby any water formed
such as glycine, alanine, valine, leucine, and the
like; dlbasic acids, such as oxalic acid, malonic‘
by the esteri?cation reaction can be continuously
removed. from thevsystemr will, in general, be
acid, methyl malonic acid, succinic acid, maleic
acid, fumaric acid, and the like; aromatic car
boxylic acids, such as benzoic acid, anthranillcv
acid, salicylic acid, phthalic acid, and the like;
' and aryl-substituted . aliphatic acids,
The esteri?cation reaction maybe carried out
acids, such as glycollic acid, lactic acid, alpha
‘found advantageous fromthje standpoint of the
yield, of ester securedpas well’as- from the stand
point of the considerable ‘reduction in time nec
such as.
essary to complete the reaction. ,
- phenylacetic acid, hydrocinnamic acid, phenyl
One suitable'methodrfor e?ecting the esteri?
propionic acid, cinnamic acid, and the like. ‘ .
cation processes of the‘ present invention'com
Such esters maybe regarded as having’ the
prises re?uxing; the’ derivatives ‘with est'eri?ca
following structural formula
tion reagents for aperiodfo'f several hours.
For example, salts of acetic acidsimay, be re
‘ ?uxed with indene-type halides. to produce ‘the
corresponding indene-type alcoholest'ers. ‘This
reaction may, if desired, be effected in the pres
ence of acetic acid. . '
The indene-type alcohol esters ‘thus produced
'30 may be suitably separated: from the halogen salts‘
in which one of the group consisting of m and n , > in’ the reaction mixture,'f_or example, by ?ltra- ‘
is an —OOC—X group, in which X is hydrogen;
r If acetic acid has been'employ'ed in the esteri?
alkyl, such as methyl, ethyl, propyl, butyl, amyl,
alkaline solutionn
_ '
40 puri?ed‘in anydesiredlmanner.
For example, 'thereaction mixture may,‘ if de
sired,~be<repeatedly extracted with any suitable
' solvent; such as’ ethe'r'i'or benzene, to increase.
Esters in which R1 to Rs are-all hydrogen, or
esters in which all but one of R1 to Rs are hydro
gen are frequently preferred.
The indene-ytypealcohol ‘esters obtained by the
processes herein. described; may be isolated and
Such esters will be referred to herein as indene
acid may thenpbeneutralized‘such as with an
aryl, such as phenyl and naphthyl; or substituted 1
aryl, such as tolyl, xylyl, phenyl methyl, and the
like; the other of said group being hydrogen,‘ and
cation reaction, it maybe removed such as by dis
tillation under reduced pressure. Any unremoved
and the like; alkenyl,,such as vinyl;j‘substitu‘ted
alkyl, such as chloromethyl, hydroxy methyl, and
the like; substituted alkenyl, such as methyl 'vinyl';
> R1 to Rs has the same meaning as before.
the yieldand'purityof' the esters therein. ,
The extracts may then be combined and dried
over a' drying agent such as, for example, anhy
drous sodium sulfate, after which the extraction
solvent employed may be removed by distillation
'. _
The use of alkyl esters of indene-type alcohols
I as plasticizing agents gives unusually good results
in practically all cases. The acetic, propionic,
at atmospheric pressure. The residue may then
butyric, and Valerie acid esters of l-indan'ol and
Z-indanol and methyl l-indanol and methyl 2 50 be fractionally distilled in vacuo to obtain a puri
?ed ester of‘ the desired type.
indanol are particularly desirable plasticizing
Mixtures of two or more indene-type alcohols
and/or derivatives, such as a mixture of indene
Such esters may be prepared by the reaction of
alcohol and methyl indene alcohol, may be esteri
the desired indene-type alcohol. or mixtures‘ of
indene-type alcohols. or derivatives of indene 55 ?ed,‘ if desired, to give a mixed ester. In this
manner. estershaving almost any desired range
type alcohols containing an atom or group capable
of volatility, and/or other, characteristics may be
of being replaced with an ester group corre
agents for synthetic rubber.
sponcling to the desired acid or mixture of acids, (
with the desired acid or anhydride, or salts or
derivatives thereof.
obtained. 3
v60 acids, ‘or derivatives thereof may be reacted with
’ ' one or’ more indene-type‘ alcohols, or derivatives
The _conversion 'of indene-type derivatives to
' indene-tyne alcohol esters 0+: desired acids may i
bevcarried out in any suitable manner, and with
Any suitable esteri?cation reagent, such as‘ an
dene hydrohalide may be reacted with asalt of '
acid. its anhvdride, its salt or mixtures thereof,
‘mav be employed as desired.
For examnle. acetic acid or acid halides thereof- _
Illustrative of the salts of acetic ‘acid which may '
be employed’ as esteri?cation reagents may be
the desired acid to obtain. an‘indene-type alcohol
ester fraction.v Mixtures containing the desired
proportion of indene and methyl indene halides
_ - suitable for use in my process may be obtained,
tyne alcohols or metallic derivatives thereof- to '
‘ acetates, and salts of acetic acid roav be used
for the conversion of indene-type halides to ace-‘ '
thereof, to give mixed esters’ possessing desired
physical properties.
For example, a mixture containing the ‘desired
proportion of indene hydrohalide and methylin
* any suitable esteri?cation apparatus.
may be employed for the conversion of indene-'
In a similar manner, a mixture of two or more
for example, by adding a hydrogen halide to a
mixture of indene and methyl indene under the
proper conditions to give‘ the desired mixture of
indene-type halides.
Similarly, a mixture of fatty acids, such‘ as
9,41 1,948
' thetic, rubber is a preferred embodiment oflthis
Examples of the rubber ,,or_ rubber-like mate
acetic or butyric acids, or derivatives thereof, may
be reacted with one or "more indene-type alcohols,
or derivatives thereof, such as a mixture of indene
alcohol and methyl indene alcohol.
rials with which esters of the type described here
in may be compounded are the various grades and
types of natural rubber and rubber-like materials,
and synthetic rubbers or elastomers, such as, for
When mixtures of such esters are obtained, they
may if desired .be separated into fractions con
taining the individual compounds by any suitable
method, such as for instance byfractionation.
example,-those obtained by the polymerization of
one or more diolefines, or 'substituents thereof,
I have found that certain indene-type alcohols
have a pronounced tendency to dehydrate, even
such as butadien'e, isoprene, piperylene, 2-chloro
butadiene, and the like, either alone, or in admix
ture, or in combination with one'or more unsatu
rated and/or reactive compounds or materials
‘such as ole?nes, unsaturated nitriles, acids, esters,
_ upon standing at room temperature; consequently '
indene-type alcohols should be esterifled as soon
as possible after formation, and vprecautions
should be taken to avoid dehydrating conditions
during esteri?cation.
ethers, ketones, aldehydes, and/or substituents
thereof, such as, for example, styrene. acrylic hi.
trile, isobutylene, acrylic esters, and the like. Im
portant examples of synthetic rubbers or elasto
mers are those’obtained by the copolymerization'
I prefer to prepare indene-type alcohol esters
by the reaction of an indene-type halide with a
metallic salt of the desired acid.
The indene and/or substituted indene used in
the practice of my invention may be obtained 20 of one or more diole?nes with (1) acrylic nitrile, '
(2)' s'tyrenepr substituents thereof, and/or (3)
from any desired source although Igenerally pre
' isobutylene or similar ole?nes, These materials
_ fer to employ fractions obtained upon the frac~
7 are known in the art under different trade names,
t‘ionation of light oil obtained by the pyrolysis of
such as, for example, Buna, Buna S, Buna N, Per
.' bunan, Chloroprene, Neoprene, Ameripol, I-lycar,
petroleum or of petroleum hydrocarbons, as such
fractions are substantially free of coumarone
and/or substituted coumarcne.
Butyl rubber, and the like.
‘ .
The quantity of esters of the type described
In the case of indene, I prefer to use fractions
> herein which may be incorporated in natural or
boiling mainly in the range of 1'75 to 190? C., and
synthetic rubbers, or elastomers, may be varied
over very wide limits, depending upon the prop
In the case of substituted indene I prefer to use 30 erties desired. ,, Thus, for example, quantities
" fractions boiling mainly in the range of 190 to
varying from a few percent, or less, to an amount
220° C. Such fractions may be further subdi
equal to, or greater than, the quantity of rubber,
'_ vided, if desired, to give‘ fractions boiling mainly
more preferably 177 to 185° C.‘
or rubber mixture, employed in the composition,
in'the range of (a) 190 to 200, (b) 200 to 210, and
be used. I prefer to use from 2% to 50%,
(c) 210 to 220° C., respectively, The unsaturated
and more particularly from 5% to, 30% of such
hydrocarbons present in such fractions are com
esters ‘by weight of the rubber‘.
prised mainly'of methyl indene.
In addition-to ‘esters of the-type described
The procedure maybe illustrated by the'fol- I
lowing examples.
herein, other ingredients which- may be incor
4.0 porated in natural rubber and/or synthetic rub
ber compositions“ include vulcanizing agents
Example 1.
and/or accelerators, such as, for example, sulfur
or sulfur-containing compounds such as tetra
‘A 900 cc. portion of alight oil. indene fraction
methyl-thiuram disul?de mercaptoarylenethia
having a mid-boiling point of 181° C. and contain
- ing 88.4% indene was ‘mixed with 2% methyl al
cohol, cooled to 0° C., and saturated with hydro
gen chloride. The indene hydrochloride obtained 7
was hydrolyzed with 1.5 liters of water and slight
ly more than the calculated amount of CaCOz by
heating at 60", C. for 2 hours. The oily layer was
zoles, such as mercaptobenzothiazole, benzothia
zyl disul?de, litharge, and dithio carbamates; pig
ments, such,as, for example, magnesium oxide,‘
zinc oxide, and lead oxide; antioxidants. such as,
for example, phenyl-alpha-naphthylamine (Neo
separated, dried rapidly with anhydrous sodium
zone A), and phenyl-beta-naphthylamine (Neo
zone D); reinforcing pigments, such as, for ex
sulfate, and fractionated at a pressure of 10 mm.
- ample, carbon blacks, such as channel black, clay,
of mercury, absolute, to isolate l-indanol.
The l-indanol obtained (B. P.=115-125° C.)
then may be esteri?ed according to the ‘methods
described previously.
Example 2
One liter of the indene fraction used in Example
1 was cooled to 0° C., 20 cc. of methyl alcohol was
added, and hydrogen chloride was passed into
the mixture until the theoretical amount had been
absorbed; The product was diluted with 500cc.
of acetic acid and 10% more than the calculated
amount of anhydrous potassium acetate, added.
The mixture was re?uxed for 5 hours, after which
the gelatinous precipitate of KCl was ?ltered off
and the ?ltrate distilled at a pressure of 10 mm.
of mercury absolute. ' l-acetoxyindane boiling
at 110-121‘? C. at -10 mm.'. was obtained. The ester
is light in color, unusually stable, and possesses a v
pleasant, fruity odor.
and blanc ?xe; ?llers and/or diluents, such as,
for example, lithopone, barytes, whiting, and as- _
bestine; other softeners and plasticizing agents
such as, for example, para?in wax, factice, di
butyl phthalate, tricresyl phosphate, pine oil, oils,
fatty acids, and synthetic or natural resins or
resinous materials.
A preferred embodiment of the invention is the
use of esters of the ‘type described’ in conjunction
with resins, such as those derived by the polymer
iz‘ation of light oil and/or coal tar fractions, con
taining coumarone and/or indene or the resins -
derived by the polymerization of the high-boiling '
monomeric material derived from tar by ?ash
distillation and/or solvent extraction processes,
and/or other organic liquids, such as the high
boiling aromatic oils derived by the flash distil
lation and/or solvent extraction of tar, as soften
ing agentsfor natural and/or synthetic rubber.
A preferred embodiment of this invention is the
:use of an aromatic oil of the typedescribed in
vcombination with one or more resinous materials
The use of alkylor mixed alkyl estersjof l-in
ldanol and/or 2-indanol as a plasticizing agent or
agents for natural, and more particularly syn 75 and an ester of the type described as a softener
$411,943 1 _ _
- for natural and/or synthetic rubber compositions.
A preferred resin for incorporating-with the ester‘
Ekrample' 6
_ A synthetic rubber tire: tread mix may be com
and aromatic oil is the resin obtained by the poly-4
pounded asffollows: v '
merization, by thermal and/or catalytic methods,
of.- certain high-boiling monomeric material
- '
separated in monomeric ‘form'from tar formed , >
Parts by
cpmponém '
during the production ofv combustible gas byproc
esses involving' the pyrolytic decomposition of. _
Neoprene.v .......... _-__‘ ____ __’___.'_ _____ __r.“ ______ _
Zinc oxide .... _ .'_ _'__ _-
petroleum oil with or without the ‘aid of catalysts.
Such resins may be formed in‘ situ in' aromatic
oils’of the type described herein.
_ '
_n n
blac ......... __
l-aeetoxyindane- - J- _'_ _ - -
Another'desired resin which may‘ be incorpo'f
Sulfur-“___”. ______ _>_;_"_ _______ .-. ______ __, _______ -_- _________ ._
rated‘in the ester as a softener for natural-and/or
synthetic rubber is the ‘resin derived by the poly-1v
merization of petroleum and/or'coal tar frac
Example 7 ,
tions containing indene and/or coumarone.
Other desirable ingredients which may be‘
Parts by
blended with an ester of the type described either
alone or in combinationwith one or‘ more resin
ous materials and/or aromatic oils, as a softener 20
____ __
____ _.
Zinc oxide'.__.__ ’
Channel black. _
for natural and/or synthetic rubber include the
dimers of petroleum or coal: tar fractions con
Age Rite Resin
taining indene and/or coumarone, dibutyl
phthalate, tricresyl phosphate; and pine oil.
Stcaric acid.
Reclaimed rubber is also included among the 25
materials which may be plas'ticlzed with the es
ters herein described, together - with natural
Sulfur- _ _
Altax __________________________________________________ _.
Pine tar
_-_ _.._
> Example‘ 8
and/or synthetic rubber, and, with or without
other ingredients; .
be mixed .orcco'rnpounded with the naturalrubber ' '
and/iorsynthetic rubber. on mixing or compounda '
Parts by
‘ Component
Butadiene-styr'ene rubber_.___'..-.__L ______________ __'___'_
The ester 'or esters, and other. ingredients,v may
l-acetoxyindane .... ._' __________________________________ __
ing rolls‘or'millsj ‘for ‘they maybe compounded by
Resin obtained from monomeric material boiling above
210° C.‘ and isolated‘ from petroleum'tar
Carbon black
_ any other ‘method known in the art, The rubber.v
3 -.
composition‘then' may be vulcanized, if desired; 35 Suliu
1 by any of the'methods employed for this purpose
f in _the art,
Me ‘"1525 '
Zinc oxide _____ __;_._.
Phenyl-alpba-naphthylamine _______________ __‘___V______ -.
~ -
Examples of rubber compositions containing : 7'
; estersof the type described herein. are as follows:
Example‘ 9 .
T V‘ Example 3
Parts by
Resin obtained from monomeric material boiling above
210° C. and isolated from petroleum tar ______________ __
Carbon black
Butadiene-acrylie nitrile r'ubber- _ ; __________ - _'_ ....... _l-acetoxy'indane ........ ___ _____________________________ __
Sulfur ______ .1.
l. 5
l. 5
Zinc oxid ___
50 Phenyl-alpha-naphtbylamlnc.-
Example 4
Example 10
- Component
Pale crepe rubber..._. _________________________ ___ ______ _'__
no oxide ______ _.
Resin obtained from monomeric material
210° C. and isolated from petroleum'tar
l-acetoxyindane ___,
0. 6
Stearic acidl ____ _ .-_-_
l-acetoxyindane _______________________________________ --
Carbon black
60 ,Slllflll'; ________________________________________________ __
Mercaptobenzothiazole ..... ..
Phenyl-alpha-naphthylamine ____________________ ___.
l. 25
Example 11
Parts by
210° C_. and isolated from petroleum tar ______________ ..
Parts by
Channel black._
Zinc oxide. .‘.-
i-acetoxyindane ................. __‘. ____________________ __
210” C. and isolated from petroleum tar ______________ _.
Stearie acid ........... l.
Mercaptobenzothiazole._._. ............................ -.
‘Resin obtained from monomeric material boiling above
Sulfur ________________________________ __
Butadiene~isobutylene rubber ____ _.' ................... _-
Resin obtained from monomeric material boiling above
Example 5
A natural rubber ‘tire tread mix may be com
pounded as follows: ‘a
Sulfur __________________________________ ..
Parts by
l-acetoxyindane. -
selected from the group consisting of natural
The foregoing compositions may be sheeted
.out, shaped and vulcanized, if ‘desired, such as
by the application of a temperature of, say,140° C.
rubber and rubber-like polymers of butadiene-. .
1,3, isoprene, piperylene, and 2-chloro-butadiene-. '
1,3 admixed with a carboxylic acid ester of one,v .
in a press for a period of, say, 45 minutes. Other.
proceduresmay, of course, be used, if desired.
of a group cdnsisting'of indanols and alkyl sub
‘ Rubber-ester compositions .of- the type de
' scribed, either as such or with the incorporation
stituted indanols.
2. As a new compositionof matter, a rubber-like , '_
butadiene-1,3-styrene copolymer, and as a plas
ticizer therefora carboxylic acid ester or one-of
a group vconsistingv of indanols and alkyl substi-' _
of other ingredients such as the resin and/or
aromatic oil derived from monomeric material
boiling above 210° C. and isolated fromv petroleum.
‘ tuted indanols..
tar, may be used for a variety of purposes, such
3. A rubber composition‘ comprising a synthetic
as for the manufacture vof tires, tubes, and other
objects. and as adhesives, coating, impregnating,
and waterproo?ng agents. Such. compositions
_may or may ‘not be vulcanized‘p'rior to, during,
or subsequent to the use. thereof.
v~Rubber has been de?ned in the prior art as
. rubber resulting from the copolymerization of. ’
butadiene-1,3 with acrylic nitrile ‘and as a plus-1
ticizer therefor a carboxylic acid ester of one
of a group consisting of indanols and alkyl sub
stituted indanols.
; i. As anew composition of matter, natural rub
' A. “An organic materialwhich shows a high -) ber plasticized with a carboxylic acid ester 01.’ one
elasticity’ of 100 percentor more at room tem 20 of a group consisting of indanols'imd alkyl sub
perature and which ‘does not lose, thisgproperty
upon storage at room temperature for. consider- ‘
able peri ."
stituted indanols.
‘ '
5. As a- new composition of matter, a material . "
selected from the group consisting of naturalrub
B. “A rubber is a substance which-shows an . ber ‘and rubber-like polymers of butadiene-I'B,
elasticity of 800% or more with a quick' return 25 isoprene, piperylene, and 2-chloro-butadiene-1,3
admixed with a fatty acid ester 'of an idanol as a. '
(snap) at temperatures at which natural rubber
plasticizing agent.
shows the same effect and which does not lose
natural rubber.”
should stretch readily to a considerable degree
and after'release retract forcefully ‘and quickly.”
For the purposes of the claims, I prefer the
following definition:
“The 'term rubber. is intended to include elas
ber and‘ rubber-like polymers of butadiene-1,3,
isoprene, 'piperylene and 2-chloro-butadiene-1,3
admixed with l-acetoxyindanol as a plasticizing
' C. “In order to qualify as a rubber, a material
6. As a new composition {of matter," a material
selected from the group consisting of natural rub
> this property upon storage anysooner than does
7. As a new compositionof matter, a material
35 selected from the group consisting of natural
rubber and rubber-like polyme.-s of bu‘tadi’ene-i
1,3, isoprene, piperylene, and 2-chloro-butadiene
tomers, whether natural or synthetic, and whether
or not admixed with other ingredients such as '
1,3 admixed and a carboxylic acid ester of an
pigments, softening agents, etc. in the vulcanized
or unvulcanized state, the said elastomer being
(1) capablev of vulcanization such asby the ap 40 8. As a new composition of matter, a material
selected from the group consisting of natural rub
plication of heat when in admixture with sulfur
ber and rubber-like polymersof butadiene-1,3,
or other vulcanizing agent, or otherwise, (2)
isoprene, piperylene, and 2-chloro-butadiene-_-1,3
slightly soluble or substantially insoluble in bodied
with a carboxylic acid ester of a methyl _
drying oils such asbodied linseed oil. and (3) 45 admixed
indanol as a plasticizing agent.
capable, either in the unvulcanized state or at
9. As a new composition of matter, ‘a ‘material
‘some stage in the vulcanization thereof,‘ of being
selected from the group consisting of natural rub
stretched readily to a considerable degree and,
ber and rubber-like polymers of butadiene-1,3,
after release of the applied stress, retracting
isoprene, piperylene and 2-chloro-butadiene-1,3
forcefully and quickly."
~ 7 5
plasticized with a butyric acid ester ‘of an indanol.
While various procedures and formulas have
10. As a new article of manufacture, a vul- _
been particularly described these are of course
canizate obtained by the vulcanization of a rub- .
subject to considerable variation. Therefore, it
ber composition comprising a material selected _
will be understood that the foregoing speci?c ex
from the group consisting of natural rubber and
amples are given by way of illustration, and that
changes, omissions, additions, substitutions and/ or 55 rubber-like polymers of butadiene-'1,3, isoprene,
piperylene, and 2-chloro-butadiene-1,3 admixed
modi?cations might be made within the scope
with a carboxylic acid ester of one of a group
of the claims without departing fromthe spirit
consisting of indanols and alkyl substituted in
of the invention, which is intendedto be limited
only as required by the prior art.
I claim:
1. As a new composition of matter. a material
indanol as a plasticizing agent.
danols as a plasticizing agent.
FRANK J. sonar.
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