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Патент USA US2406717

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_ Patented
. ‘Q
‘ UNI-ran jsrA'rEs PATENT old-‘ICE
vnm; ESTER
Charles Allen Thomas,'Da'yton, Ohio, assignor to
Monsanto Chemical Company, St. Louis, Mo., _.
a corporation of Delaware
Application October a, 1940,_
Serlal No. 360,224
(a. 260-86)
10- Claims.
This invcnhon relates to new and useful poly
>' tested on a Massachusetts Institute '01 Technol
1 merizates and a process of preparing the same.‘
' ogy Folding Endurance Testén'manufactured by »
It is an object of the present invention to pre
pare polymerizates with new and improved prop
the, Tinius-Olsen Testing Machine Company,
Philadelphia, Pennsylvania.
- .
Another object is to provide conjoint 5
polymers with increased ?exibility. It is-a fur-, ,
ther object to prepare co-polymers with in
creased light resistance. Other objects of this
A ?lm prepared .
from a commercial co-polymer of vinyl chloride
and vinyl acetate when subjected to the same
‘folding test failed after substantially 600 folding
cycles. :‘I'he'lightstability‘ of a ?lm of the co- ‘
invention will become apparent hereinafter. .
polymer of vinyl ?uoride and vinylacetate was
It has been found, according to the present in 10 found to be exceptional. After 21 *days'exposure
vention, that by subjecting mixtures of vinyl
to the rays from an 8-1 type General Electric
?uoride and vinyl esters of lower aliphatic acids
Company sun lamp at a-distance of substantially
to polymerizing conditions, new polymerizates
16 inches, this polymerizate was still tough and
can be prepared with unexpected and improved
colorless. In contrast, to this outstanding light '.
properties. The following are speci?c'examples 15 resistance, a commercial co-polymer of vinyl
illustrative but not limitative of the present in
chloride and vinyl aceta..e had started to discolor
after an. exposure of 14 days under similar con
? ditions and had become brittle after an exposure
Example 1
- Substantially 14 parts by weight of vinyl ace
tate and substantially 0.029 part by weight of
benzoyl peroxide were placed in a suitable vessel
capable of withstanding pressure, as for exam
: period of 19 days.
pie, 9. stainless steel bomb. ‘The bomb and its -
contents were then cooled ina suitable manner,
as for example, by immersing the bomb in liquid
Thereafter,v substantially 12.4 parts by
A mixture of substantially 15 parts by weight
of vinyl ?uoride, substantially 15 parts by weight
of vinyl formate and substantially 0.0375 part by
weight of benzoyl peroxide was prepared for poly- ‘.
merization in substantially the same manner as -
the mixture in Example 1. The present mixture
was then warmed with suitabel mixing to sub
weight of vinyl ?uoride were distilled into the
_ ’ bomb and the bomb closed.
Example 2
The bomb and its
stantially 40° C. and maintained at substantially
contents were then warmed with suitable mixing
that themperature ‘for substantially '7 days at a '
to ‘substantially 50° C. and maintained at sub
pressure between about 320 and 480' pounds per
stantially that temperature andv at a pressure
' square inch gauge pressure.
between about 340 and about 420 pounds per
The resulting co-polymer was treated in a
square inch gauge pressure for substantially 12
manner similarto that employed in Example 1
days. The resulting co-polymer, a solid material,
was treated in a suitable manner, as for ex 35 and a puri?ed solid product was thus obtained
ample, by ‘dissolving the product in su?icient
acetone to produce a solution with a solid con
tent of about 5%, ?ltering this solution, precipi
that was tough, elastic and substantially color
less. This polymerizate was found to be soluble
' in acetone, chloroform and dioxane, swelled by
' contact with benzene and ethyl acetate and in
' tating the polymerizate with water and ?nally
drying the precipitated resin .by evacuation at 40 soluble in hexane and ethyl alcohol. This prod
room temperature.
} uct', like that in Example 1, had a softening point
well below its decomposition point. A ?lm of
this material was transparent, extremely ?exible
The co-polymer, thus puri?ed, was a tough,
‘slightly elastic, resilientand substantially color
be soluble in acetone, ethyl acetate, benzene, 745
and showed good resistance to light. 1
It is evident that the new ,‘products of the
ethylene dichloride and dioxane. It was only
swelled ly contact with ‘ethanol and was insolu
speci?c examples, possess many valuable and un
ble in hexane. Furthermore,‘ this product was
found to possess a moderate softening point‘ well
expected properties that make the use of these
new materials advantageous for manyof the ap-;
less material. This polymerizate was found to
present‘ invention, as illustrated by‘the foregoing
below its decomposition point.
In addition to the foregoing valuable proper
50 plications of plastic materials. ' Furthermore,
other polymerized or .polymerlzable materials, I
ties, it was found that a film of the product in
this example was transparent and substantially
plasticizers, ?llers, coloring‘ agents and other
materialsmay be added to the products of this
water resistant. Also, such a ?lm withstood sub
invention in any suitable manner, such as by ,
stantially .6300 foldingcycles before failure, when 55 mixing in a Banbury mixer or on mixing rolls.
2,406,717 '
2. A process of preparing a conjoint polymer
comprising polymerizing a mixture of vinyl ?uo
The products of this invention may be mixed,
rolled, calendered, extruded, molded, or other
ride and vinyl acetate in the presence of an or
wise formed with and without thecaddition of
added materials of the types listed above. Ii’
desired, these new co-polymers may be dissolved
ganic peroxide catalyst.
3. A process ofpreparing a co-polymer com- .
prising polymerizing in admixture vinyl ?uoride
and vinyl acetate in the presence of benzoyl per
in suitable solventswith and without added ma
terials, applied in any desired manner, and the
solvent then removed by evaporation.
4. A process of preparing aco-polymer com
There are many variations that may be intro
duced into the process or preparing the new poly 10 prising polymerizing a mixture of vinyl ?uoride
- and vinyl formate in thepresence of benzoyl per
merizates or this invention. Thus, for, example,
the process or this invention is not limited to any _
particulartypeof. polymerization apparatus, type
..prising polymerizing a mixture comprising vinyl
' of catalyst or other means of accelerating the
polymerization, amount of catalyst, polymeriza
‘tion temperature, polymerization pressure-ex
5. A process of preparing a co-polymer com
15 ?uoride and a vinyl ester of a lower saturated
‘fatty acid, the vinyl ester of the lower aliphatic
acid being present in said mixture in an amount
at least equal to the amount of vinyl ?uoride
cept to avoid escape of volatile components, dura
_ .tion of polymerization or method of puri?cation.
While vinyl ?uoride and vinyl esters oi! the lower
6.1%. process of preparing a co-polymer com
aliphatic acids may be mixed in any desired pro 20
prising polymerizing a mixture comprising vinyl
portions and the mixture polymerized, it is gen?uoride and vinyl acetate, the vinyl acetate be
erally desirable that the vinyl ester of the lower
ing present in said mixture in an amount at least
aliphatic acid be present in an amount at least
equal to the amount of vinyl ?uoride present.
equal to the amount of vinyl ?uoride present.
Furthermore, the mixtures of vinyl esters'ot lower 25 '7. A co-polyiner of vinyl ?uoride and a' vinyl
ester of a lower saturated fatty-acid.
aliphatic acids and vinyl ‘?uoride may be P019
8. A co-polymer of vinyl ?uoride and vinyl ace
merized in suitable solvents or in suitable liquids '
that are non-‘solvents for the monomeric and/or
9. A process which comprises polymerizing a
polymeric materials. Thus, the particular prop
erties desired in the product and the use'to which 30 mixture 01' vinyl acetate and vinyl ?uoride, with
vinyl acetate in greater proportion by weight than
the material is to be placed can govern to a con
vinyl ?uoride, at a temperature of_ about 50° C.
siderable degree the exact polymerizing conditions
and at a pressure between about 340 and about
420 pounds per square inch gauge with benzoyl'
This invention is limited solely by the claims
35 peroxide as a catalyst.
attached hereto.
10. A eopolymer or vinyl ?uoride and vinyl for
What is claimed is:
mate. ‘
i. A process or‘ preparing a‘co-polymer com
prising subjecting to polymerizing conditions a
mixture‘ or vinyl ?uoride
a vinyl ester of
lower saturated fatty acid.
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