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Iégi?Iziliii Patented Junev 13, 1950 2,511,424 UNITED STATES PATENT, OFFICE CHLORINATED ACRYLIC ESTERS Vigen K. Babayan, Teaneck, N. J.,'assignor, by ' mesne assignments, to Pierce Laboratory, Inc., New York, N. Y., a corporation of New York No Drawing. Application September 15, 1945, Serial No. 616,659 3 Claims. (or. 260-895) ' 2 This invention relates to chlorinated acrylic product made in this way has a softening point acid ester polymers, such polymers being here of about 140° C. after referred to as acrylates. Various factors to be kept in mind in connec As is known, polymerized acrylates, for ex tion with the foregoing are as follows: ample of molecular weight upwards of about‘ First, with reference to the polymers contem 2,000, constitute more or less plastic or waxy plated for use according to this invention, it is masses, some of which are of rubbery consistency. noted that the polymeric acrylic acid esters are These materials have a number of industrial uses, assumed to have a structural formula such as but because of the physical consistency, and also given just below, in which R represents an alkyl for other reasons, the materials are not well or aryl group of‘ at least 57 molecular weight. suited for certain other purposes requiring a more solid or harder type of resin. I have found that by extensive chlorination of certain ones of the acrylate polymers, it is pos iégi?iziliii sible to alter the physical consistency so as to H Li Jni yield products which are solids, having softening The acrylate radical of the polymer is enclosed points upwards of 80° 0., sometimes even as high in large brackets in the above formula, and this as about 175° 0., and no longer manifesting the radical or unit is, of course, repeated a multi characteristic rubbery or waxy nature of the un plicity of times in the molecule, depending upon chlorinated materials. In view of this striking 20 the molecular weight of the particular polymer. change in physical consistency, the chlorinated For the present purposes, it is contemplated that products of the present invention may be em the molecular weight of the polymer employed ployed for various purposes for which, heretofore, should be at least 2,000 and preferably upwards certain other materials were used, for example, of 5,000, for instance from 5,000 to 30,000. methacrylate polymers, such as methyl meth An important consideration is that the acrylic acrylate. acid ester be one having an ester group higher In addition to the foregoing, the invention is than propyl, i. e., formed with a radical “R” of the of advantage since the chlorinated products have molecular weight indicated above, for instance, other improved properties, such as increased solu formed with an alcohol higher than propyl. I bility in various organic solvents, increased ?ame 30 have found that chlorination in the manner de and ?re-proofness, increased resistance to at scribed above of acrylate polymers having an tack by other chemicals, and capability of being ester group of the molecular weight of propyl or spread in tough sheets or ?lms which are trans lower, for instance, esters formed with methyl parent and substantially colorless, this being in alcohol or ethyl alcohol, yields only a relatively distinct contrast with the same unchlorinated 35 low combined chlorine content, and further that acrylate polymers which, in general, manifest such chlorinated lower esters of acrylic acid re some appreciable opacity. tain more or less of their original rubbery con A typical procedure for producing a product I sistency. This ‘is in distinct contrast with the according to the invention is here given for illus consistency of higher esters, for instance poly trative purposes. The acrylate polymer, for ex 40 meric butyl acrylate which, although having a ample butyl acrylate, is dissolved in carbon tetra rubbery consistency prior to chlorination, is con chloride heated close to its boiling point, to give verted to a solid upon chlorination, having a a solution of about 1% concentration. Chlorine melting point even as high as 150° C. Polymeric gas is then bubbled through the solution in the butyl acrylate is a particularly effective ester to presence of catalytic light, the temperature being 45 employ in producing products according to the maintained close to the boiling point of the sol present invention. ' vent.‘ The bubbling of chlorine is continued un With further reference to the esterifying agent t? the chlorinated acrylate product contains with which the ester is formed,'it may be men about 65% combined chlorine, representing an tioned that such agents may be either alkyl or increase in weight in the ?nal product of about 50 aryl, may be either straight chain or branched 185%. The solution of the chlorinated product chain, and may be either saturated or unsatu in the carbon tetrachloride is then mixed and rated. Esters formed with alkyl alcohols 'are par agitated with methyl alcohol, as the result .of ticularly effective, such for example as the butyl which the chlorinated product precipitates as a ester, mentioned above, and also iso-butyl, lauryl white powder. The chlorinated butyl acrylate and cetyl esters. 8,511,424 - 3 4 The solvent employed during chlorination is this theoretical consideration need not be dis advantageously a chlorinated solvent, such as cussed in detail herein, although'as already in carbon tetrachloride, chloroform, etc., and the dicated, an average of at least two chlorine at concentration of the solution prepared for chlori oms per acrylate radical is of importance in se nation is preferably relatively low, for example curing the type of product contemplated by the below about 35%, depending on the solubility invention. Most advantageously, three or more characteristics of the particular polymer being chlorine atoms are substituted for hydrogen in chlorinated and also on the viscosity of the so each radicaL- When employing polymeric butyl lution. It is of particular advantage to em acrylate, as is preferred, the substitution of three ploy quite low concentrations, for instance, be chlorine atoms yields a product containing in low about 15%, since the solution tends to be the neighborhood of 46% combined chlorine, come quite viscous toward theend of the chlo which represents almost a 100% increase in rination and this makes bubbling of the chlo weight of the ‘product. With .butyl acrylate I rine gas through the solution quite di?icult, un have even been able to substitute chlorine atoms less the concentration is kept low. With this in 15 for as many as eight out of the twelve hydrogen . mind, I prefer to use concentrations ranging atoms present in each radical of the polymer. from about 1% to about 15%. Acetic acid'inay ‘With lauryl acrylate this ?gure is more than also be used as solvent, in which case concen doubled. - trations up to about 35% may be employed. Upon attaining the desired degree of chlori Chlorination in acetic acid usually proceeds more 20 nation, the solution of the chlorinated acrylate slowly, in view of which more vigorous chlorina is then mixed with a substantial volume of a tion conditions are of advantage. precipitant, i. e., a liquid in which the chlorinat As chlorination proceeds the temperature of ed product is substantially insoluble and in the solution tends to rise, and in most cases it which the chlorination solvent is soluble. When is of advantage to apply some heat, since the a chlorinated solvent is used, various alcohols rate of the chlorination reaction is thereby ac such as methyl alcohol, ethyl alcohol and also celerated. Initiation of chlorination is promoted certain aliphatic hydrocarbons may be utilized by pre-heating the solution before passing the for precipitation. When employing acetic acid chlorine therethrough, and I prefer to maintain as solvent it is not necmsary to use precipitants a temperature of at least 60°‘ C. throughout the 30 such as alcohols, since even cold water will serve period of chlorination. However, the tempera the purpose. It is of importance during this pre ture should be controlled so as not to cause ex cipitation that the mixture be thoroughly and cess'ive loss of solvent. Refluxing is also of ad vigorously agitated in order to place the chlori vantage for this purpose. nated product in such ?nely divided state that - Exposure of the solution to catalytic light ma 35 occlusion of any appreciable quantity of carbon terially accelerates the chlorination and for this tetrachloride or other chlorination solvent is Purpose ordinary incandescent electric lamps prevented. In consequence the precipitate forms placed close to the outside of a glass chlorina as a fine powder which can readily be dried and tion vessel will be found effective. The chlori which retains free ?owing powdery consistency. nation does not require the presence of catalytic (0 This is of great advantage in subsequent handling light but may even be performed in a completely and use. _ ‘ opaque reaction vessel, although in this case Other methods for separating the chlorinated maintenance of the temperature close to the material from the chlorination solvent may also boiling point of the solvent is of advantage in be employed, provided such methods are con order to promote the substitution of chlorine 45 ducted in a manner affording'such extensive sur atoms for hydrogen in the molecule. face area exposure of the chlorinated product ‘The combination of both high temperature that occlusion of solvent within the particle is (as speci?ed above) and strong catalytic light is prevented. As illustrative of other methods of preferred and will yield products of surprisingly separation, reference is made to mixture of the high chlorine content, even in a relatively short 50 solution of the chlorinated material in the chlo time, for instance, even up to about 75% com rination solvent with boiling water, which will bined chlorine, which corresponds to an increase result in volatilization of the solvent (assuming in weight of the product as high as 300%.
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