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Патент USA US2121695

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Patented‘ June 21,':1-938
1 2,121,595
Rowland Hill, Biackley, Manchester, England,
assignor to Imperial Chemical Industries
Limited, a corporation of Great Britain
No Drawing. bpplicationoctober 13, 1938, Se
rial No. 105,444. In Great Britain October 23,
1985 ‘
3 GlaimsThis invention relates to a process for the‘
manufacture of valuable polymerization prod
ucts from. cyclohexene oxide.
(Cl. 280-2)
with a small amount (2 parts) of active carbon
and ?ltered to remove kieselguhr. _- The benzene .
is then evaporated from the ?ltrate by heating '
at 80°- C. under ‘reduced pressure (20-30 mm.).
The residue so obtained is a pale straw-colored, 5
It is known to obtain resinous polymers by sub
5 jecting cyclohexene oxide to very high pressures
hard, somewhat brittle transparent resin. It dis- ,
for several days in presence of a small amount of
benzoyl peroxide.
‘solves readily in cold benzene, toluene or tur
pentine but is insoluble inv cold methylated spirits
According to the present invention I ,obtain
resinous polymers by treating cyclohexene oxide
or ethylene glycol monoethyl ether. It is freely
soluble in linseed oil, tung oil or a linseed “stand” 10
10 in the presence of an active earth or clay as poly->
merization catalyst. By an active earth or clay
I mean a ?nely-divided, highly-absorbent clay
or earth such as, for example, bentonite, fuiler’s
The resin produced in accordance with the
foregoing example is in addition to being com
patible with drying oils also compatible with rosin
modi?ed glyceryl phthalate resins and other rosin 15
earth or talc or a diatomaceous earth such as
15 kieselguhr.
In carrying the invention into e?ect it is not
modi?ed polyhydric alcohol-polycarboxylic acid
resins. The resin of the foregoing example is
necessary to use very high pressures. Thus, in
also compatible in equal proportions with nitro
presence of active earth catalysts polymerization
cellulose and ethyl cellulose, and with cellulose
acetate in the ratio of 60 partsjof the polymer to 20
may conveniently be e?ected at atmospheric
2o pressures by the application of moderate heat.
Polymerization may be carried out in presence
or absence of a solvent or diluent. The reaction
‘after it is initiated is highly exothermic and may
be controlled by cooling. After the initial violent
as reaction subsides the reaction mixture is heated
100 parts of the acetate.
It is to ‘be observed that although the alkylene
oxides can be polymerized by a large number of
agents such as calcium chloride, metallic sodium,
ultra violetlight. etc., these agents are ineilec- 25
to maintain reaction temperature until a product. tive for polymerizing cyclohexene'oxide, and the
oxides mentioned herein. ‘
of the desired degree of condensation is obtained. other
The present invention is applicable to all car
The polymerization products obtained accord bocyclic
epoxy compounds in which the; oxygen
ing to the invention-are usually in the form of a
is linked to adjacent carbon atoms‘,v which are 30
30 hard, somewhat brittle, transparent mass. The ' ‘both
members of a carbocyelie group. I may for
products are readily soluble in organic solvents
use alkyl substituted cyclohexene oxides, '
such as benzene, toluene or turpentine and in dry—, e. g.,_ methyl,
dimethyl, isopropyl, butyl, etc.,
ing oils such as linseed oil. Becauseof their solu
bility in organic media and their other physical cyclohexene oxides as well as dlhydronaphtha
lene. oxides. vPartially or completely hydrogen- '35
35 properties, the polymerization products are valu
ated substituted or v unsubstituted dihydro
able ingredients for varnish compositions, nitro
naphthalene oxides may also be used. Carbo
cellulose lacquers and the like.
The following example, in which the parts are , cyclic epoxy compounds containing less than six
atoms may also be used. Compounds of
by weight, illustratesbut does not-limit the in carbon
the kind mentioned herein may be- interpoly- 40
40 vention:
merized, as for instance by using any combination
' of these compounds.
One (1) partv kieselguhr is suspended in 50
parts cyclohexene oxide (“Organic Syntheses",
45 vol. 5, page 35, London,,1925), the mixture is
heated to 100° ‘C. to initiate the reaction in a
vessel ?tted with are?ux condenser. After they
initial violent reaction subsides the temperature
is adjusted to 110 to 115° C. Polymerization, ‘ae
50 companied by an increase in viscosity. is rapid
at ?rst. After 4-6 hours, the reaction mixture.
changes from a mobile into a moderately viscous
?uid at reactionv temperature. After 40 hours,
the reaction mixture is very viscous and the
55 viscous mass is then dissolved in benzene, boiled v
The preferred materials, '
however, are the carbocyclic epoxy compoimds
of thehydroaromatic seriessuch as cyclohexene
As vmany apparently widely different embodi
' ments of this invention may be made without de
parting from the spirit and scope thereof, it is
to be understood that I do not limit myself to the
speci?c embodiments thereof except‘ as de?ned 5o in the appended claims. _
1. A process for vproducing polymers which
comprises heating in the presence-of a catalyst
an epoxy compound in which the oxygen is linked 55 I
to eiiec-ent carbon atoms in e cerbccyclic ring,
and ccntin
the heating until said epoxy
' S. A process which comprises heating cyc1o~
hexene omde with an active earth and after the
eompcund is polymerized, said ceteiyst being‘ reaction has been initiated maintaining the tem
selected from the class of active earths and cieys. pereture from 110 to 115° C. until a. resinous
2. In a. process for making resins from cyclo
product soluble in drying oil is obtained.
hexene oxide the step which comprises heating
cyciohexene oxide with an active earth.
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