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United States Patent Office Patiented (Oct 3,056,673 United States Patent Office Patiented (Oct. 2, 1962 1. 2 manipulation of incident light to enable one and the same 3,056,673 PRINT-OUT AND DEVELOPABLE-OUT System to be either negative working or positive working PHOTOGRAPHIC PROCESSES as desired. Eugene Wainer, Cleveland Heights, Ohio, assignor to AS has been explained in the aforesaid copending ap Horizons Incorporated, Cleveland, Ohio, a corporation 5 plications, certain organic halogen compounds appear of New Jersey to be effective sources of highly reactive free radicals No Drawing. Filed Apr. 18, 1960, Ser. No. 22,703 on exposure to light of suitable wavelengths. When 7 Claims. (CI. 96-48) these free radicals are formed in the presence of certain arylamines or N-vinylamines or combinations thereof, This invention relates to photography. More particu 0. highly useful color changes of permanent nature take larly it relates to compositions which are sensitive to place making such reactions of utility in the photographic light and which are suitable for photography and photo art. On a practical basis, the majority of photographic graphic reproduction purposes. The invention relates to exposures are limited by the specific nature of a light the production of stable, colored, print-out, and develop Source and, generally speaking, the light source utilized able out images produced by exposing to light and/or to 5 is not normally the ideal one for a specific combination light and heat, combinations of organic amines, specific of ingredients. organic halogen-containing compounds which produce I have found that by Suitable choice of the organic free radicals on exposure to light, and various Substrates halogen compound which represents the source of the for suitable disposition of the active agents with or with free radicals, the desired photochemical reaction can be out minor additions for specific and minor purposes and 20 made to take place within a relatively narrow spectral more specifically this invention relates to the control of range which, in many cases, can be matched with levels spectral sensitivity in the production of such images. As of high intensity from a specific light source to enable one the result of the ability to control these photochemical to make best use of the energy available from such light reactions as a function of the specific devices for imparting source. I have further found that such reactions will spectral sensitivity over relatively narrow ranges, a multi 25 not take place at wave lengths substantially longer than plicity of photochemical reactions of useful nature is avail in the region of peak sensitivity and, more important, able in one and the same composition as a function of nor in wave lengths very much shorter than the region the manipulation of the wave length of the incident light. of peak sensitivity. As a result, by utilizing free radical In various copending United States patent applications sources which have individually different peak sensitivities filed by me including Serial Nos. 787,112, filed January 30 (for decomposition to produce free radicals under the 16, 1959; 841,459, filed September 22, 1959; 841,460, influence of light), reaction control is available for a filed September 22, 1959; 842,569, filed September 28, number of useful end items by the use of such free 1959; 1,161 and 1,162, both filed January 8, 1960, I have radical sources in conjunction with light of widely dif described the utility of photochemical reactions between ferent spectral sensitivity ranges. certain organic amines and certain organic halogen com The nature of the organic halogenating compound de pounds which act as sources of halogen free radicals on termines, in the main, the area of peak sensitivity and the exposure to light. As described in the aforesaid applica spectral range of sensitivity. In general, it appears that tions, suitable organic halogen compounds are halogen the higher the bond dissociation energy for free radical ated hydrocarbons in which the active halogen atom is formation, the shorter the wave length at which the free attached to a carbon atom to which there is attached not 40 radical source exhibits peak sensitivity. more than a single hydrogen atom and as more specifi The organic halogen-containing compounds suitable cally described in my application Serial No. 787,112, filed for the purposes of my invention may be divided into January 16, 1959, the activation energy of the halogen three groups. The first group of free radical sources ex containing free radical is the most important factor in hibits peak sensitivity in the spectral range 5100 to 5500 determining the suitability of the halogenated hydro 45 A. and includes carbon tetraiodide, tribromoidomethane, carbon for the process. It appears that in order for the trichloroiodomethane, dichloroiodomethane, and dibro halogenated hydrocarbon to be effective, it must have an moiodomethane. Each of these, it will be noted, is a energy of dissociation or in other words, an energy of halogenated methane in which at least one hydrogen has formation of the free halogen radical of not less than been replaced by iodine, and at least two of the remain about 40 kilogram calories per mol. 50 ing hydrogens have been replaced by a halogen selected I have now found that the spectral sensitivity of such from the group consisting of iodine, bromine and chlo photochemical reactions can be controlled by proper rine. Of this group, the compound carbon tetraiodide choice of organic halogen-containing compound which is preferred since it is a solid at room temperature and acts as a source of free radicals and that such control is readily prepared in pure state. The liquids are also ef provides an expanded facility for use of these reactions 55 fective materials but present difficulties in utilization at and a degree of flexibility not available through random room temperature because of their liquid state. This de use of such organic halogen compounds. fect can be eliminated through encapsulation techniques Principal objects of this invention are: to provide a by which means liquids may be incorporated in a solid chemical means of control of spectral response of a film and retained indefinitely therein without evaporation. photochemical reaction within the category described in 60 The second group of free radical sources exhibits peak my copending applications and hereinafter more fully sensitivity in the spectral range 3900 to 4000 A. and described; to utilize the means of control of Spectral re includes carbon tetrabromide, trichlorobromomethane, sponse to facilitate the preparation of the photosensitive and dichlorobromomethane. Each of these, it will be compositions with respect to the type of light that may noted, is a halogenated methane in which at least one be used during the preparation and prior to exposure; hydrogen has been replaced by a bromine atom and at as a result of the means of control of spectral sensitivity 65 least two of the remaining hydrogens have been replaced to increase the effectiveness of the photochemical reac by a halogen from the group consisting of Ci and Br. tion by making fuller use of all the energy available from Again, for reasons given in the previous paragraph, the a specific light source; to make possible the development compound carbon tetrabromide is preferred. and utilization of more than one photochemical reaction The third group of free radical sources useful for the in one and the same material through manipulation of 70 purposes of my invention exhibit peak sensitivity in the spectral ranges of incident light; as a result of such region of 3000 A. and includes carbon tetrachloride, 8,056,678 3. hexachloroethane, and tetrachlorotetrahydronaphthalene. SERIES III.-N-WINYLCARBAZOLE Each of these, it will be noted, is a chlorinated hydrocar bon in which any carbon atom to which a chlorine is at III(a) III(b) III.(c) tached, is attached to not more than one hydrogen. For practical purposes hexachloroethane and tetrachlorotetra 5 150 cc. benzene. 150 cc. benzene. 150 cc. benzene. hydronaphthalene are preferred since they are stable solids 15 g. eicosane (M.P.s 15 g. eicosane (M.P. 15 g. eicosane (M.P. 38° C). =38° C). =38° C). at room temperature. 5g. hexahexacontane 5 g. hexahexacontane 5 g. hexahexacontane Three main groups of organic amines useful for the 20g.(M.P. N-vinylcarbazole. = 103° C). 20 (M.P.g. N-vinylcarba- =103° C). 20g.(M.P. N-vinylcarba = 103° C). purposes of my invention have been described in my co zole. zole. pending applications. The first group consists of amines O 25 g. carbon tetra. 16 g. carbon tetra- 12 g. hexachloro wherein the amine nitrogen is attached to aryl or modi iodide. bromide. ethane. fied aryl substituents or, more specifically, carbocyclic, e.g. benzene or modified benzene ring substituents. Di SERIES W.-N-WINYLCARBAZOLE phenylamine is representative of this group. The second group comprises amines in which the amine nitrogen con 5 IV(a) IV (b) IV(c) stitutes a portion of a heterocyclic ring. Indoles, pyr 150 cc. benzene. 50 cc. benzene. 150 cc. benzene. roles and carbazoles are representative of the group. The 15 g. ecosane 15g. eicosane. 15 g. eicosane. 5 g. hexacontane. 5 g. hexacontane. 5 g. hexacontane. third group of compounds represents an especially pre 0.2g. azo-bis-isobutyr 0.2g. azo-bis-isobu 0.2g. azo-bis-isobu ferred species of the preceding groups and is comprised Onitrile. tyronitrile. tyronitrile. 20 20g. N-vinylcarbazole. 20 5. N-vinylcarba- 20 g. N-vinylcarba of N-vinylamines, and particularly amines in which the ZOle. zole. amine nitrogen is attached to a vinyl group and is also a 25 g. carbon tetra- 16 g. carbon tetra- 12g. hexachloro member of a six-membered ring or a member of other iodide.
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