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United States Patent Office Patented May 30, 1972 2 Camera to Obtain a Satisfactory Exposure When a Cloud 3,666,352 Passes Overhead

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United States Patent Office Patented May 30, 1972 2 Camera to Obtain a Satisfactory Exposure When a Cloud 3,666,352 Passes Overhead 3,666,352 United States Patent Office Patented May 30, 1972 2 camera to obtain a satisfactory exposure when a cloud 3,666,352 passes overhead. RATE CONTROLLED PHOTOCHROMC LENSES It has also been proposed to disperse mercury thiocar OF VINYL CHLORIDE-VINYL ACETATE CO POLYMER CONTAINING A MERCURY THO bazone photochromic compounds in solid, unplasticized CARBAZONE COMPOUND resins, such as polystyrene, cellulose acetate and the like. Charles A. Wagner, Towson, Md. (32 Virginia Ave., These require 10 to 60 minutes for color development Shrewsbury, Pa. 17361), and Herman B. Wagner, Tri and reversion at ambient temperatures. It is only by heat angle Hill, Box 22, R.D. 1, Perkasie, Pa. 18944 ing at about 180° F. that the time can be shortened, and No Drawing. Continuation-in-part of application Ser. No. this expedient, which is impractical in any event for sun 474,956, July 26, 1965. This application Jan. 22, 1970, glass lenses and camera light filters, cuts the reversion time Ser. No. 5,095 O only to 5 minutes or more. nt. C. G02c 7/10, G02b 5/20, F21v 9/00 It has now surprisingly been found that if mercury thio U.S. C. 350-160 8 Claims carbazone compounds are used with a particular polymer, plasticized with a particular amount of plasticizer, lenses and filters with remarkably rapid response and rever ABSTRACT OF THE DISCLOSURE 15 sion will be obtained. Mercury thiocarbazone compounds dispersed in a A primary object of this invention is to provide photo solidified plasticized resin composition consisting essen chromic lenses for sunglasses, these having a very much tially of vinyl chloride copolymerized with, e.g., not less more rapid adjustment to incident light intensity than than 5 mol percent of vinyl acetate and laminated in a heretofore accomplished. sandwich between two transparent glass or plastic lay 20 Another object of this invention is to provide photo ers provide lenses with extremely rapid color responses chromic sunglass lenses having substantially increased to incident light and reversion to dark-adapted states. durability toward photo-chemical degradation. A further object of this invention is to provide auto matic light filters for camera lenses, these compositions and constructions providing for simple and very rapid CROSS-REFERENCE TO RELATED response and adjustment to the light intensity reflected APPLICATION from the photographed subject. This application is a continuation-in-part of copend ing application Ser. No. 474,956, filed July 26, 1965, now DESCRIPTION OF THE INVENTION abandoned. 30 These objects and all others readily apparent to those This invention relates to certain photochromic com skilled in the art are secured according to this invention positions and devices, providing for regulated speed, and With photochromic lenses exhibiting rapid color response mode of response to light, and of recovery from the and adjustments to incident light comprising a pair of effects of such irradiation. adjacent transparent layers having interposed between 35 them an intermediate layer of a mercury thiocarbazone BACKGROUND OF THE INVENTION compound admixed with a vinyl chloride-vinyl acetate co Certain substances have phototropic characteristics and polymer resin and a plasticizer, with which the resin is change in color or in degree of light transmission as a capable of fusing at a temperature of below 120° C., there result of exposure to light. Among the relatively large 40 being from about 1.0 to 10 parts by weight of plasticizer number of phototropic substances, however, only a small per part of resin and the quantity of mercury thiocar number possess the property of reversibly responding to bazone compound ranging from about 0.01 to about 0.10 irradiation and assuming a steady state of light transmit milligram per square centimeter of lens area, the amount tance that is dependent on the intensity of the incident of plasticizer and quantity of mercury compound being radiation. While some of these substances are stable 45 Selected to achieve complete color response and adjust under practical conditions and are capable of undergoing ment in less than 100 seconds. a large number of repeated cycles of color change by ir The present invention also contemplates a method of radiation with Subsequent complete reversion to initial producing such lenses. Also contemplated is an improve color, none of them, as far as is now known, when dis ment in the method which increases durability of the sub persed in solid transparent compositions, will rapidly re 50 stances which comprises applying over the mercury thio spond and revert at ambient temperatures. : carbazone layer a protective compound to screen out light It will be apparent, if transparent, photochromic solids of ultraviolet wavelengths. satisfying the rigid requirement of rapid response, i.e., of The mercury thiocarbazones contemplated to be used the order of 100 seconds or less at ambient temperatures, in this invention are of the formula: i.e., 65-90 F., could be provided, they would satisfy a 55 number of useful applications. For example, the sand wiching of such solids between transparent layers will provide photochromic lenses for sunglasses, and cameras, as well as light filters for cameras and the like, window and Sun visors and shades. It has been proposed to disperse mercury thiocarbazone 60 photochronic compounds in plasticized vinyl chloride resins for coating toys, e.g., dolls, which mimic a sun burned effect when exposed to sunlight. Such coatings H serve admirably the purpose simulating over three to R-Nen-CeN-N-R four minutes in strong sunlight the darkening observed 65 s with the human skin and gradually reverting over eight to ten minutes to a lighter color when shielded from the light. Unfortunately, such gradual changes are not useful for efficient sunglasses-consider, for example, the need wherein R, RR3 ad R4 are the same or different and are for rapid response in driving an automobile into a high 70 aryl groups, R is an aryl group and X is a halogen atom, way tunnel. Consider also the need quickly to adjust a an alkyl group or an aryl group. The two groups R in 3,666,352 3 4 the second formula need not be the same. The compounds components of the liquid are varied inversely as the thick can be made, for example, as described by Wobling and ness of the liquid interlayer. * * - - - - - - - - - - - - - - - - - -- Steiger, Z. angew. Chem. 46, 279 (1933). Especially use The light filter, described above, is mounted over an ful mercury thiocarbazones are mercury bis-diphenyl thio eight-millimeter movie camera lens, and used to photo carbazone, monodiphenylthiocarbazone mercuric chlo graph subjects under various intensities of illumination. ride, fluoride, iodide or bromide; monodinaphthylthiocar In the instance here cited an unadjusted “f-stop” of value bazone mercuric chloride, fluoride, iodide or bromide; 4 is maintained constant throughout, so that all regula monoditolylthiocarbazone mercuric chloride, fluoride, tion of the light admitted to the camera chamber is ac iodide or bromide, mercury bis-dinaphthylthiocarbazone, complished by the light filter. mercury ditolylthiocarbazone, ethyl mercuric diphenyl 10 The subjects photographed range in reflected light in thiocarbazone and phenyl mercuric diphenylthiocarba tensity from about 40 to 200 lumens. If these are to be ZO. properly photographed, without the photochromic light The resin is a vinyl chloride-vinyl acetate copolymer, of filter above described, an "f-stop' manual adjustment of a type which is freely available commercially. The resin value ranging from 5 to 11 will be required. With the can be made by copolymerizing vinyl chloride and vinyl 15 photochromic filter, of the type above described, no such acetate together, in known ways. Polymerization can be, manual adjustment is needed, and satisfactory exposure for example, by suspension, emulsion, bulk or solution is obtained. methods. The molecular weight can vary fairly widely In the table following there is shown the percent light without affecting the results. The amount of vinyl acetate transmission (at 6000 A.) when this filter has reached a co-monomer can vary over a wide range, e.g., from about 20 steady state of equilibration to surrounding light of vary 1 to about 99 mol percent, but best results in terms of ing intensity. The data indicate the manner in which the rapid response and reversion, will be obtained if the resin filter compensates its transmittance to the incident light contains not substantially less than about 5 mol percent intensity received from the photographed subject. of copolymerized vinyl acetate. The upper limit of vinyl TABLE 1. acetate content is not critical. Surprisingly, as will be 25 shown hereinafter, vinyl chloride homopolymers are not Light percent of incident: Light reflected from subject suitable in the present invention because of slow reversion 62 ------------------------------------- O time, but only a minor amount of vinyl acetate is suffi 40 ------------------------ -a - a - - - - - - rs - as 100 cient to effect a remarkable change in the rate of color 26 ------------------------------------- 200 change in the lenses. For example, 9-10 mol percent of 30 22 ------------------------------------- 300 copolymerized vinyl acetate causes almost a nine-fold 17 ------------------------------------- 500 reduction in response time in comparison with a vinyl 14------------------------------------- 700 chloride homopolymer. 12 ------------------------------------- 1000 The plasticizers also are freely available commercially Example 2 or easily prepared by known ways. The only requirements 35 are that they be non-reactive with the photochromic com A higher molecular weight, powdered vinyl chloride pounds and that they fuse with the resin at a temperature homopolymer resin is used in place of the vinyl chloride below about 120° C. Illustrative plasticizers are high mo vinyl acetate copolymer of Example 1. With a heating lecular weight esters, such as abietates, adipates, abelates, temperature of 110' C., a translucent but not transparent benzoates, biphenyls, citrates, fumarates, glycerol esters, 40 filter is obtained.
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