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Патент USA US2404267

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Patented July is, 1946
2,404,267 \
Carl ,E. Barnes, Acton, Masa, assignor to Polaroid , _
Corporation, Dover, Del., a corporation of Del
No Drawing. Application February 20, 1942,
Serial No. 431,732
1 Claim. (Cl. 260-486‘)
This invention relates to a new and improved
synthetic'resin and more'particularly to alpha
(o-chlorophenyl) ethyl methacrylate.
An object of the invention is to provide such '
a resin which is useful in the formation of hard,
transparent, optical elements possessing relative
ly high indices of refraction.
Further objects of the invention are to provide
a polymerized resin of the character described
copper cloth was added to the mixture as an in
hibitor of polymerization. The mixture was then
permitted to stand at a temperature of from 50
to 60 degrees C. for several hours and was dilut
ed with ether and extracted several times with
dilute sulphuric acid. It was then washed sev
eral times with dilute sodium hydroxide and il
nally with water. The ether layer was then con
centrated and distilled under reduced pressure,
and tow provide a copolymer of a resin of the 10 alpha (o-chlorophenyl) ethyl methacrylate being
character described with a. resin from the class
distilled o?.
consisting of the unsaturated methylene com
Monomeric alpha (o-chlorophenyl) ethyl
pounds, and more speci?cally to provide a co
methacrylate is a liquid with a boiling point of
polymer of a resin of the character described
approximately 146 degrees C. at 11 mm. pressure.
with a methacryiate resin.
15 In polymerizing the monomer, either alone or
Other objects of the invention will in part be
obvious and will in part appear hereinafter.
coniointly with a resin from the class consisting
of the unsaturated methylene compounds, poiy- .
There is a pressing demand for a synthetic
merization is preferably commenced at a tem
resin composition which may be used in the for
perature of from about 60 to 65 degrees 0., and
mation of optical elements such for example, as 20 the temperature is preferably raised before poly
lenses, prisms, and the like and which may pref
_merization is completed to approximately 130
erably be cast or molded to the desired form. A
degrees C.
preferred resin is one which may be cast into the
The polymeric valpha (o-chlorophenyi) ethyl
desired form by, for example, polymerizing the
methacrylate has a density at 20 degrees C. of
monomer in a suitable mold or by advancing the 25 "1.269. It has an index of refraction MD”) of
polymerization of the partially polymerized ma
1.562 and a reciprocal dispersion of 37.5, It is
terial in a suitable mold. This invention contem
substantially colorless, hard, brittle and trans
plates the provision of new synthetic resins or
plastics which are particularly useful in the pro
It will be noted that the refractive index of
duction of products of the character described. 30 the polymer of alpha (o-chlorophenyl) ethyl
More speci?cally, this invention contemplates
methacrylate is above 1.55, which is a preferred
the provision of synthetic resins which, when‘
condition. The polymer is, however, somewhat
polymerized, give a transparent, hard, substan
brittle, and-where it is to be employed under con
' tially colorless product having a relatively high
ditions such that it may be subjected to shock, it
index of refraction and which is suitable for use 35 may be desirable to combine it with plastics
in the production of optical elements of the
whose polymers are somewhat tougher. This is
character described.
The compositions of the present invention
comprise resins from the class consisting of al
~ especially true where the high refractive index is
not required. In this connection it should be
noted that alpha (o-chiorophenyl) ethyl meth
pha (o-chlorophenyl) ethyl methacrylate and 40 acrylate may satisfactorily be copolymerized with
copolymers thereof with other resins from the
virtually all the polymerizable ‘unsaturated
class consisting of the unsaturated methylene
methylene compounds to produce products hav
Alpha (o-chlorophenyl) ethyl methacrylate
ing diverse and varied physical and optical prop
erties. Suitable compounds for use in forming
may be prepared in the following manner, which 45 copolymers of the type described with alpha
is given as illustrative of one method of prepar
(o-chlorophenyl) ethyl methacrylate are methyl
ing the material. A suitable quantity of o-chlo
methacrylate, ethyl methacrylate, isopropyl'
rophenyl methyl carbinol having a boiling point
of 123 degrees C. at 18 mm. pressure was pre
methacrylate, ter-butyl methacrylate, cyclohexyl
methacrylate and other esters of alpha-metha
pared from o-chlorobenzaldehyde and methyl 50 crylic acid: the vinyl esters such as vinyl formatc,
magnesium bromide in ways known to the art.
vinyl acetate, vinyl propionate and the vinyl
156.5 grams (1 mol) of ‘o-chlorophenyl methyl
ester of chloracetic acid, etc; the vinyl ketones
carbinol was mixed in a suitable ?ask with 154
such as methyl vinyl ketone; styrene; furylethyl
grams (1 moi) of methacrylic anhydride and 79
ene (vinyl furane). Other suitable materials for
grams (1 mol) of pyridine. A small amount of
use in the formation of copolymers falling with
in the scope of this invention‘ are the esters of
itaconic acid, the esters of acrylic acid, and the
vPolymerization of the products of this inven
tion may be accomplished preferably by heating
esters of methylene malonic acid.
mixtures of monomers or the slightly polymerized
It is to be understood that the list of substances
materials at relatively low temperatures, or Just
given is not all-inclusivealthough it is believed a. above the melting point of the monomer, until
that the materials mentioned constitute the pre
a hard product is obtained, when polymerization
ferred substances for use in the present inven
may be carried forward to a desired point at sub
It is also to be understood that, if desired,
stantially increased temperatures. Higher tem
peratures of polymerization generally increase
hardening agents may be employed in small or 10 the brittleness of the product. It is, of course,
substantial percentages. Any of a vast number
to be understood that where molded optical ele
'of suitable hardening agents may be used; A
ments are to be produced, the surfaces of the
preferred hardening agent for use with copoly
mold should be optically smooth as the molded
mers comprising methyl methacrylate is either
product will have substantially the surface prop
methacrylic acid or acrylic acid, although other 15 erties of the mold.
known hardening agents such as methacrylic an
Since certain changes may be made in the
hydride or allyl methacrylate may be used suc
above article and different embodiments of the
invention could be made without departing from
While a preferred product is one which is
its scope, it is intended that all matter contained
transparent and which may be molded during 20 in the above description shall be interpreted as
polymerization into a suitable optical element,
illustrative and not in a limiting sense.
it is to be understood that products which are
It is also to be understood that'the following
translucent or even opaque and hence useless in
claims are intended to cover all of the generic
the formation of optical elements may be sat
and speci?c features of the invention herein de
scribed and all statements of the scope of the in
vention which, as a matter of language, might
be said to fall therebetween.
‘ isfactorily employed for other purposes where
particularly hard, readily molded, polymerized
plastics are desirable, and such products com
prising alpha (o-chloropheny'l) ethyl methacry
late or a copolymer thereof with an unsaturated
methylene compound are to be deemed to fall 30
within the scope or this invention.
What is claimed is:
Alpha (o-chlorophenyl) ethyl methacrylate.
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