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United States Patent Office Patented Jan 'S 3,075,907 United States Patent Office Patented Jan. 29, 1963 1. 2 saturated compounds copolymerized therewith, said com 3,075,907 PHOTOPOLYMERIZATION OF MONOMERS CON. position being sensitized by the addition of sulfur com TANING WNYTL GROUPS BY MEANS OF SILVER pounds. It is suggested that in such reproduction an ap COMPOUNDS AS CATALYSTS propriate body of the liquid, copolymerizable mixture Steven Levinos, Vestal, N.Y., assignor to General Aniline containing the sulfur sensitizer and usually containing a & Film Corporation, New York, N.Y., a corporation of copolymerization catalyst such as a peroxide is exposed Delaware by contact or by projection to the desired image. Pref No Drawing. Filed Feb. 17, 1958, Ser. No. 715,528 erably, exposure is prolonged under the action of light at 1. Claims. (Cl. 204-158) least until partial polymerization, i.e., a gel stage, is 10 reached. If desired, the light may then be removed and The present invention relates to the formation of solid the final cure effected by heating the mixture until final polymers by photopolymerization of normally liquid or cure is attained. The light source used was sunlight or Solid monomeric vinyl compounds while employing a ra light from a carbon arc, i.e., UV, light. diation-sensitive, non-oxidizing silver compound as the Murray in U.S.P. 2,475,980 suggests the photopolym catalyst or promoter of the reaction. 15 erization of addition products of piperic acid and piperi The polymerization of vinyl compounds is a phenome dine in the presence of an accelerator such as benzoyl per non Well recognized in the art. Extensive work has been oxide. Murray prefers to initiate polymerization by ex done in the manufacture and exploitation of polyvinyl posure to sunlight and to harden the relatively soft resin compounds and the literature is rife with procedures lead thus obtained by a brief heat treatment. ing to the preparation of such polymers ranging from 20 Oster in "Photographic Engineering,” volumes 3-4, viscous liquids to hard brittle or elastic solids. 1952-53, discloses on page 177 photopolymerization with Generally, monomeric vinyl compounds are polym visible light of vinyl monomers in the presence of a erized or copolymerized by subjecting the monomer(s) reducible dye such as Rose Bengal and a mild reducing in Solution or in a dispersion to the action of elevated agent. It is indicated by Oster that his system, one of the temperatures in the presence of oxygen or a peroxide 25 few suggested for photopolymerization by visible light, catalyst such as benzoyl peroxide, hydrogen peroxide and may be used for the imagewise formation of polymers, the like. For instance, British Patent 304,681 of 1928 i.e., in the production of printing plates. He emphasizes refers to the polymerization of acrylic acid by heat in the that his method must be effected in the presence of at presence of oxygen or organic peroxides while using a mospheric oxygen. solvent such as acetone. Copolymers of mixtures of vinyl 30 None of the prior art systems, however, constitutes a compounds such as ethyl acrylate with vinyl acetate or simple convenient method of directly forming high molec with styrene are prepared in a similar fashion. ular weight solid polymers in a relatively short period of It is recognized that certain of the monomeric vinyl time and without resort to elevated temperatures. Thus, compounds are sensitive to UV light and may be polym the products of Jones are of low molecular weight. The erized by irradiation with UV or a source thereof such polymers of Gerhart produced by use of light are in the as sunlight in the presence or absence of a catalyst. Thus, same category and, in this connection, it is noted that Ger Ellis in “The Chemistry of Synthetic Resins' (volume II) hart's exposure is prolonged until partial polymerization (1935) states at the bottom of page 1072 that methyl to the gel stage is reached. The final cure is not affected acrylate, on long standing in the Sunlight, changed into by light but by heat. In this respect, Murray's process is a transparent, odorless mass of density 1.222. At the 40 similar. Oster's system is complicated in its resort to the bottom of page 1070, the same writer indicates that acrylic use of a reducible dye and a reducing agent in the presence acid polymerizes under the influence of light or heat in of atmospheric oxygen. the presence of a catalyst. On page 1071, however, it I have now discovered that monomeric vinyl compounds is noted that photopolymerization of acrylic acid is in which are normally liquid or solid, i.e., liquid or solid at hibited by the presence of oxygen. It is to be emphasized, room temperature, may be directly photopolymerized in however, that such procedures involving the use of light essentially short periods of time to high molecular weight to effect polymerization proceed at a very low rate and/or solids by subjecting a solution or dispersion of the mono with the formation of relatively low molecular weight mer or mixtures thereof in the presence of water to the polymers. Typically, an aqueous solution of acrylamide action of radiations ranging in wave length from 10 containing N,N'-methylene-bis-acrylamide will polymerize 50 to 10-10 cm. and preferably to visible light while using a upon exposure to sunlight for one hour. The polymer radiation-sensitive, non-oxidizing silver compound as the formed, however, is not a hard mass. On the other hand, catalyst or promoter. acrylamide plus the same cross-linking agent will not The particular mechanism by which I achieve photo polymerize when exposed for 90 minutes to the light of a polymerization has not been ascertained and is not self 150 watt tungsten light source at a distance of 12'. evident. It is quite possible that the photopolymerization In recognition of the sensitivity of certain vinyl com is due to the presence of free radicals produced during pounds to UV radiation, suggestions have been made that the decomposition of the radiation-sensitive silver com polymers of such monomers be prepared either in bulk pound. A free radical, it may be noted, is a compound or imagewise by subjecting the monomers to the action with an unpaired electron, usually a fragment of a larger of UV radiation in the presence of a promoter for the 80 molecule which has been split by heating. The mecha reaction. Thus, Jones in U.S.P. 2,533,166 polymerized nism involving free radicals is explained, for instance, on acrylamide and certain derivatives thereof such as N page 98 et seq., "Scientific American,” September 1957. ethanol acrylamide and N-ethanol methacrylamide by UV Regardless of the theory involved, the fact remains that irradiation in the presence of organic solvents. It is said radiation-sensitive silver compounds have the very claimed that the products produced are soluble in water 65 unusual ability under the action of radiation ranging in and are compatible with gelatino silver halide emulsions, wave length from 101 to 1010 cm. of initiating and con as a consequence of which they may be used as gelatin tinuing the polymerization of monomeric vinyl com substitutes in such emulsions. pounds to high molecular weight solids. Most important Gerhart in U.S.P. 2,673,151 disclosed photographic re is the fact that this system, unlike practically all prior production by subjecting to the action of light a copolym 70 systems, is also effective when using visible rather than erizable mixture of (A) polyesters of alpha-beta ethylenic, UV radiation. alpha-beta dicarboxylic acids and (B) ethylenically un The direct formation of solid polymers by the irradia 3,075,907 3. 4. tion, with rays of the aforesaid wave length, of monomers it is recognized that the molecular weight and hence containing vinyl groups in the presence of water and a the ultimate hardness of a vinyl polymer can be increased radiation-sensitive, non-oxidizing silver compound as the by utilization during polymerization of a small amount catalyst constitutes the purposes and objects of my in of an unsaturated compound containing at least two vention. terminal vinyl groups each linked to a carbon atom in a It has been ascertained that the characteristics of the straight chain or in a ring. These compounds serve to radiation-sensitive, non-oxidizing silver compounds to ini cross-link the polyvinyl chains and are generally designat tiate photopolymerization of vinyl monomers is generic ed as cross-linking agents. Such agents are described, for to such a class and is not restricted to a few members example, by Kropa and Bradley in vol. 31, No. 12, of thereof. Silver compounds which are active oxidizing 0. “industrial and Engineering Chemistry,’ 1939. Among agents such as, for example, silver perchlorate, are ex such cross-linking agents for my purpose may be men cluded since these react explosively with vinyl compounds tioned N,N'-methylene-bis-acrylamide, triallyl cyanurate, even in the dark and cause the vinyl compound to under divinyl benzene, divinyl ketones and diglycol-diacrylate. go change through oxidation rather than polymerization. The cross-linking agent is generally employed in an Similarly, silver compounds which decompose when stored amount ranging from 10 to 50 parts of monomer to each in darkness are not contemplated for use. part of the cross-linking agent. It is understood that the Examples of silver compounds possessing the property greater the quantity of cross-linking agent within such of catalyzing photopolymerization are: silver acetate, range, the harder the polymer obtained. silver acetylide, silver ortho-arsenate, silver ortho-arse The photopolymerization hereof, depending upon the nite, silver benzoate, silver tetraborate, silver bromate, 20 solubility of the monomer on the one hand and the silver bromide, silver carbonate, silver chloride, silver silver compound on the other, will be carried out in a chromate, silver citrate, silver ferrocyanide, silver fluoride, solvent solution of the involved compounds or in an silver iodide, silver lactate, silver fluosilicate, silver cy aqueous dispersion of such components.
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