DE2338684A1 - Photosensitive compsn. based on org. halogen - and N-vinyl cpds. with vinyl cpd. or dye for improved white colour - Google Patents

Abstract

Photosensitive compsn. contains (1) a photosensitive disperse phase, consisting of individual particles of a combination of (A) an organic halogen cpd., which forms free radicals or ions on exposure to light of suitable wavelength and has the formula R-C-X3 (in which R is halogen, (halo)-alkyl or (halo)aryl; X is halogen), (B) an N-vinyl cpd. and (C) a matl. which polymerises or fixes the unexposed parts in a white colour; in (2) an aq. dispersion medium in which the disperse phase is almost insol. The compsn. responds to actinic light in such a way that an image with selective light absorption is obtd., which is different from that of the combination and of (A), (B) and (C) and the combination polymerises, forming a white colour. (C) can be a vinyl cpd. or a thiazine or cyanine dye. Compsn. is for photography and photocopying. Clear whites are obtd., without detriment to image colour formaton, with (C) eliminating the original colour of the AB combination.

Description

Dr. D. Thomsen PATENT AGENCY OFFICE W. Weinkauff ^ f _0n ωβ · ο 53 0211

Dr. I. Ruch

, _el e _x5 - ₂ 4303topa _t 2338684

PATENT LAWYERS Some: Frankfurt / M .:

Dr. rer. nat. D. Thomeen Dlpl.-Ing. W. Weinkauff

Dr. rer. nat I. Ruch (Fudwhohl TI)

8000 Munich 2 Kalser-Ludwlg-PIatzβ 31 j _u li 1973

Matsushita Electric Industrial Company, Limited

Osaka / Japan

Photosensitive mass

The invention relates to the field of photography and, more particularly, to a photosensitive composition suitable for is suitable for use in photography or photomultiplier and which is an organic halogen compound as its main component and an N-vinyl compound and a third material whose function it is in a duplicating process to polymerize or fix unexposed parts in white color.

It is known to use photographic or photosensitive systems that use a combination of an organic

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see halogen compound (A) and an N-vinyl compound (B) which under the influence of actinic light to produce a Color reacts, included. Such systems are described in ÜS-PS 3,042,515 and 3,476,562. Describes the above-mentioned US-PS 3 476 562 a solidified new combination of compounds A and B, which in an aqueous dispersion medium is dispersed. This solidified combination of A and B can be assumed to be within of the individual particles has essentially the homogeneity of a solid solution.

As stated in the above-mentioned patent, each of the compounds A and B absorbs light by itself and. is practically colorless, while the combination of A and B has its own, moderately yellowish-blue color and - a strong absorption capacity for blue light. The change in the practically colorless compounds A and B when combined to the colored AB indicates that this combination AB is something other than a purely physical solid solution or same combination. This means that the development of the color indicates that the combination AB is a chemical combination in the form of at least one complex, if not a true chemical combination. The combination AB results when exposed to actinic light with a certain absorption wavelength or when exposed to a large one Amount of light and then heating or leaving it to stand for

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for some time a blue or greenish-blue color; or the combination AB can only be polymerized by adding them exposed to dim light or exposed to a small amount of light and heated or left for some time.

When the combination AB as a photosensitive material is used, the polymerized part serves as a white part of an image obtained. The downside, however, is in that the original color of the combination AB after polymerization by actinic light in the white parts of the image remain.

In order to overcome this disadvantage, attempts have been made, for example, non-photosensitive or non-photographic to incorporate inorganic material, such as colloidal silica powder, into the photosensitive combination AB, without affecting the photosensitivity of the combination AB. By introducing the inorganic material however, there is a secondary problem that the colored image is affected by the introduction of this inorganic material is affected.

The object of the invention is therefore a photosensitive or photographic agent or a combination by which the above disadvantages can be overcome.

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The object of the invention is also a photosensitive or photographic agent, when applied to Negative printing paper, white parts of a picture emerge clearly without impairing color formation of an image.

It has been found that an improved white color can be obtained by combining an organic halogen compound A with an N-vinyl compound B by photopolymerization when a small amount of a certain compound C is combined with or mixed in with the combination AB. In addition, the new combination ABC can enter into two separate and specific reactions, one ^of which is a color-forming reaction and the other is a non-color-forming reaction.

The invention relates to a photographic composition which (1) has a photosensitive disperse phase in the form discrete particles made from a combination of (A) an organic halogen compound that when exposed to a light forms free radicals or ions of a suitable wavelength and has the following general formula

RCX ₃

in which R (in Ha] o <jr natoin, an A] hylgru; »2, an aryl group <or a halogen-substituted alkyl <;<" ir aryl group eats v.

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BATH ORIGINAL

X is a halogen atom, a is bonded in which a vinyl group directly attached to a nitrogen atom N-vinyl compound (B), and a third material (C), which serves to polymerize in a reproducing process non-exposed parts in a white color, in (2) an aqueous dispersion medium or a solid hydrophilic film-forming carrier in which the disperse phase is practically insoluble, the coordination being so responsive to actinic light that an image of selective light absorbency is different from that of the combination and the organic halogen compound, the N-vinyl compound and the third material », and this combination is polymerized to form a white color of an image.

The organic halogen compounds which can be used according to the invention are, for example, carbon tetrabromide, hexachloroethane, pentabromoethane, iodoform, monobromotrichloromethane, ÖC, cx ¹ , Q ("tribromotoluene, bromoform and the like. Among these, carbon tetrabromide is most suitable for the purpose of the invention. The N-vinyl compound B, which is used in combination with the above-mentioned organic halogen compound and contains a vinyl group bonded directly to a nitrogen atom, is for example N-vinylcarbazole, N-vinylphenyl - <* - naphthylamine, N-vinyldiphenylamine, N-vinylindole, N-vinylpyrrole, N-vinylpyrrolidone, N-vinylsuccinimide, N-vinylacetanilide, N-vinylphenylacetamide,

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N-vinyl methylacetamide, N-vinyl diglycolylimide, N-vinylphthalimide and. like that. Also a compound with the structure of N-vinylbenzothiazoline or N-vinylbenztriazole can be used as the N-vinyl compound can be used.

The photosensitive composition according to the invention is characterized in that it contains a certain third material C in combination with the organic halogen compound A and the N-vinyl compound B. This third material C is a vinyl compound or a dye.

The vinyl compound must meet at least one of the following requirements:

1) A monomer that is produced by photopolymerization

to copolymerize as the terminal N-vinyl compound progresses able; for example acrylonitrile, maleic anhydride or the like.

2) A monomer that can photopolymerize by itself (or by using a suitable polymerization initiator), without it becoming discolored; for example styrene, acrylonitrile or the like.

3) A monomer that is present in the presence of the organic halogen compound (which acts as a polymerization initiator) to photo-

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able to polymerize without discoloration; for example Methyl methacrylate, styrene, or the like.

Examples of the vinyl compound which can be used according to the invention are allyl chloride, vinyl acetate, methyl methacrylate, styrene, fluorostyrene, chloroprene, acrylonitrile, methyl vinyl ketone, vinyl pyridine, a cyclic ether, maleic anhydride, acrylamide, isobutyl vinyl ether, p-vinyl diphenyl sulfide or the like. In contrast, the dye serves to sensitize the N-vinyl compound B to polymerize by actinic light having a wavelength different from that by which an image is formed, and is not intended to increase the sensitivity to the photo color formation of the combination ABC. Such a dye is, for example, a thiazine dye such as methylene blue or methylene green (registered trademark, CI .: Basic Green 5, 52o2o), a cyanine dye such as 1,1'-diethyl-4,4'-carbocyanin iodide, 1,1'-diethyl -io-phenyl-2,2'-carbocyanine bromide, 3,3'-diethyloxatricarbocyanine iodide, 1.1 ^l -diethyl-2.2 ^l -quinomonocarbocyanine iodide, 1,1'-diethyl-2,2'-quinodicarbocyanine iodide, 1, 1 '-Diethyl-2,2'-quinotricarbocyanine iodide, 3,3'-diethylthia-monocarbocyanine iodide, 3,3' -diethylthiadicarbocyanine iodide, 3,3 '-D'iethylthiatricarbocyanine iodide, 3, 3' -diethylselenamonocarbocyanine iodide, 3,3'-diethyl selenary amocyanine iodide, 3, 3 '-diethyl selenate tricarbocyanine iodide odcj the like.

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BATH ORIGINAL

The vinyl compound and the above-mentioned dye can be used together as the third material.

The photosensitive composition or combination ABC according to the invention can be prepared by the Starting materials A, B and C, each individually or all together, dissolved in an organic solvent, uniformly in a dispersion medium D in which A, B and C are practically insoluble, for a suitable time, at a suitable time Temperature and with suitable agitation uniformly dispersed and an emulsion containing a combination ABC in the form contains single particles.

When using a photosensitive paper sheet containing a photosensitive composition or combination ABC is coated, a print is generated, the sheet is first suitably pretreated or thermally treated and exposed imagewise to actinic light. Then the sheet thus obtained is subjected to a sensitization process, to increase the sensitivity of the exposed parts prior to thermal development. For example, it is used as a sensitizer 4- (p-Dimethylaminostyryl) -quinoline used, and actinic Light with a wavelength of 500 to 75o m is used to uniformly irradiate a leaf for a short time. Thereafter, the sheet obtained in this way is using a suitable light source or a light with certain suitable

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neter wavelength (using a filter) that different is different from the one used in the awareness process, irradiated to photopolymerize weakly exposed parts and unexposed parts and thus white or to develop medium tones of an image. This photopolymerization process can be independent of the development imagewise exposed parts can be performed and may be referred to as a "fixation" process, although it is actually serves as part of the development. Accordingly, the photopolymerization of weakly or unexposed parts can under conditions of time, temperature and intensity, i.e. one applied as a coating on a sheet Photosensitive mass can be fixed or photopolymerized by applying light of a certain wavelength to it and suspends intensity for a desired time. Tests under varying polymerization conditions have shown that the use or introduction of the third material in the combination AB acts to produce clear white parts of an image can be obtained. However, it is currently not fully understood why the use of the third material C enables a white color to be developed when the combination ABC is photopolymerized.

The dispersion medium D used in the composition according to the invention is, for example, a water-soluble natural one film-forming material such as a protein i.e. gelatin, casein or the like, or alginic acid or a water-soluble one

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- 1ο -

synthetic film-forming material, such as polyvinyl alcohol, Polyacrylic resins, polyvinylpyrrolidone, amine or aldehyde resins, Cellulose derivatives or the like.

The photosensitive composition according to the invention can still a trace of a sensitizer, a stabilizer, an antifoam agent, a surfactant or the like.

The emulsion or dispersion that the photosensitive Bulk or combination containing ABC can form a photosensitive printing material that has an excellent Photopolymerization fixation is capable of being applied to a sheet of paper with a barite coating, a plastic film Sheet of paper covered with a natural or synthetic resin Resin carries, or be applied to a glass plate or a metal foil.

The combination ABC according to the invention preferably consists mainly of a larger part of the compounds A and B and a smaller part of the third material, for example in the case of a dye 0.04 to 0.8% by weight the combination AB or, in the case of a vinyl compound, from 0.04 to 4% by weight of the combination AB. In addition, the weight ratio of compounds A to B is in the range from 10 to 80: 9o to 2o.

5098 09/0931

The following examples illustrate the invention.

example 1

20 g of gelatin were placed in 80 cm of water and allowed to swell for 2 hours. The resulting mixture was heated 3o minutes on a water bath at 80 ⁰ C and mixed by means of an operating at a high speed mixer. 10 mg of 4- (p-dimethylaminostyryl) -quinoline, dissolved in acetone, were added to the mixture with vigorous agitation within minutes. Then, while agitating at the same high speed, 5 g of carbon tetrabromide (A) and 15 mg of maleic anhydride (C), also dissolved in acetone, were added to the mixture until a substantially uniform emulsion was obtained. That is, a combination of ABC was regarded as being discontinuously and uniformly dispersed in the gelatin used as the dispersion medium D. The emulsion obtained in this way was applied to a sheet of paper with a barite coating using a bar (applicator bar) with a wet film thickness of 20 ρ. The disperse phase from the combination ABC solidified rapidly on cooling the emulsion in the film-forming material D with the formation of individual, practically non-agglomerated particles of practically uniform size. The sheet obtained with the wet coating was kept in a dark room dryer for 30 minutes, during which a dry, coherent solid film was formed.

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The sheet thus obtained was brought into contact with a negative film by a known contact printing method and 30 seconds with a 500 W reflector lamp used for color photography from a distance of 60 cm exposed and heated to obtain a positive image. The sheet thus obtained was left to stand under room light to polymerize unexposed parts and thus the unexposed parts white to develop.

For comparison, Example 1 was repeated with the difference that no maleic anhydride was added to the composition became. A white color on the obtained image had a reflection density of 0.15 to 0.3 o in terms of one blue light, while the white color of the image obtained according to the invention has a considerably low reflection density from 0.08 to 0.12 in terms of the same blue light would have. (The blue light was used for evaluation of a yellow component in the white parts).

For the measurement of the reflection density, v / eg a Macheth densitometer RD-I00R was used. A reflection. *; density from 0.08 to 0.12 corresponds to the white parts of an image obtained with ordinary photographic paper. The above test results show that the mass or combination ABC according to the invention is superior to the conventional combination AB.

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Example 2

A sheet of baryta paper coated with a photosensitive film and having a wet film thickness of 40 microns was made in obtained in the same manner as in Example 1, except that the following photosensitive composition was used:

Dispersion medium (consisting of 1 part by weight of gelatin and 4 parts by weight Water) loo g

N-vinyl carbazole (B) 5 g

Carbon tetrabromide (Λ) 5 g

Acrylonitrile (C) 0.5 g

4- (p-Dimethylaminostyryl) -quinoline 5 mg.

The obtained sheet was brought into contact with a negative film and imagewise with the light of a for 1 second 500 W xenon lamp exposed from a distance of 50 cm above the sheet in order to obtain a positive image. Then it became Leaf developed under ambient light. White parts on the received Image had a running reflection concentration of only 0.09 to o.14 for a blue light, from which the effect of the Acrylonitrile present results.

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Example 3a

■ The same kind of photosensitive composition coated sheet as obtained in Example 1 was made used to connect to a front face of a cathode ray tube with an optical fiber face on its front face (a so-called optical fiber tube) and was first exposed through a negative image. This one The negative image used means an image formed in a cathode ray tube by inversion of brightness and scanning directions is preserved. The no-exposed film was then exposed to the light of an 18o W low-pressure sodium lamp for a few seconds exposed and heated to 100 ° C. in an oven for 60 seconds to obtain a positive image.

The sheet thus obtained was used to polymerize the unexposed parts of the photosensitive film Development of an image left in room light. The white background of the picture had a reflection density of o, o8 to o, 1 for a blue light.

Example 4

In this B;! Game, the following was photosensitive Masye uses:

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Dispersion medium (consisting of

1 part by weight of polyvinylpyrrolidone

and 1o parts by weight of water) 100 g

N-vinylindole (B) 3 g

Iodoform (A) 1g

Vinyl pyridine (C) o, 2 g

Leuco crystal violet 10 mg.

The dispersion medium was heated and agitated sufficiently to obtain a uniform solution. Under Stirring at high speed by means of a rotary mixer became N-vinylindole (B) and leuco crystal violet in one dissolved a small amount of acetone so that they were miscible with one another, and then added to the solution and agitated for 10 minutes. Then, iodoform (A) and vinyl pyridine (C) dissolved in a small amount of acetone became the solution within Added for 5 minutes with continued agitation.

The solution thus obtained was applied to a polyester film using a rod.

The obtained film was instantly air-dried to form a photosensitive film.

Using a reflection method with a The reflected image of an original was made as in a conventional duplicator in which a 500 W halogen lamp

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was used as a light source for exposure, an image was focused on the photosensitive film. After 1o Second exposure, the photosensitive film was obtained for 5 seconds with light having a wavelength over 58o µm was by putting light through a 500 W reflector lamp a filter VO58 (manufactured by Toshiba Co., Ltd.), exposed to light, and then heated for development. That warmed up Sheet was left to stand under room light, leaving an image with white parts with a reflection density of 0.1 to o.15 was received for a blue light »

The image thus obtained could be used as an original for photographic reproduction, for electrophotography of the transmission type or for a negative slide projector.

Example 5

20 g of gelatin were introduced into Bo era water and Left to swell for 2 hours. The resulting mixture was poured on the water bath for 20 to 30 minutes with high-speed mixing heated to 8oC by means of a mixer. 1o g N-vinylcarbazole (B) and 1 mg methylene green, dissolved in acetone, were added to the mixture within 15 minutes with vigorous agitation added. 4 g carbon tetrabromide ΪΑ) were in acetone

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dissolved, and the solution was stirred with high speed added within 3 to 5 minutes until a uniform emulsion was obtained.

The emulsion obtained contained particles of uniform size from the combination ABC dispersed in the gelatin. the Emulsion was applied to a baryta-coated Elatt paper in a wet film thickness of 20 ti. When cooling the combination ABC rapidly solidified on the sheet and formed individual, practically non-agglomerated particles on the sheet.

The sheet coated with the wet film became one with a breeze in a dark room dryer for 30 minutes a dried film coated sheet.

A negative film was brought into contact with the sheet thus obtained in the same manner as in conventional printing Contact printing method common and was done for 3 seconds under a color reflector lamp from a distance of 6o cm above the sheet exposed and heated to obtain a positive image.

Then, the exposed sheet was filtered with visible light through a VY 47-Olas filter (manufactured by Toshiba Co., Ltd.) irradiated evenly around the non-exposed parts to polymerize for the purpose of fixation, whereby a white background of the picture was obtained.

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For comparison, Example 5 was repeated with the difference that no methylene green was added to the mass. The white colored parts or a white background color of an image obtained had a reflection density of 0.15 to 0.33 for a blue light, while the white background of the image obtained according to the invention has a considerably lower reflection density of 0.05 to 0.13 for the had same blue light. It follows that the combination ABC according to the invention of the conventional combination AB is superior.

Example 6

N-vinylindole fj g (B)

Carbon tetrabromide 4 g (A)

1,1'-Diethyl-4,4'-carbocyanine iodide 2 mg (C).

The above compounds were dispersed in a gelatin medium in the manner described in Example 5. The dispersion obtained, which contained individual particles of the combination ABC, was on a sheet of paper, the one coating of polyvinyl alcohol was applied, and the sheet thus obtained was dried using a photosensitive Mass coated sheet was obtained. A negative film was brought into contact with the sheet. The exposure took place for 5 seconds with a 300 W halogen lamp

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2333804

after which the sheet was placed in a dryer at 10o ° C for 80 seconds
was heated. The sheet thus heated was taken out of the dryer and left to stand under room light or irradiated by means of a low-pressure sodium lamp in order to polymerize unexposed parts and to develop the white background of an image. The white background had a reflection concentration of 0.08 to 0.13 for a blue one
Light.

Example 7

Iodoform 6 g

N-vinyl phthalimide 10 g

SjS'-diethylene selenadicarbocyanine iodide 2 ing

The above compounds were dispersed in a polyvinyl alcohol medium (composed of 1 part by weight of polyvinyl alcohol and 4 parts by weight of water). The obtained dispersion or emulsion was applied to a sheet of paper having a polyvinyl alcohol coating, so that a photosensitive paper sheet was obtained.
Then, a negative film was brought into contact with the photosensitive sheet. Exposure was for 5 seconds using a 500 W wolf frame and the sheet was then removed for development in a hot air draft dryer. Then the sheet was heated in this way for a few seconds with the

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Light from a 5oo W-WoI for am lamp through a glass filter VR-60 {manufactured by Toshiba Co., Ltd.) exposed so that light having a wavelength over € 00 was passed through roughly, whereby the unexposed parts of the photosensitive sheet polymerized and developed to a white color. The white parts had a reflection density of 0.08 to 0.12 for blue light "

Example 8

9 g of gelatin was mixed with 80 cm 3 of water, and the mixture was allowed to stand for 2 hours to swell the gelatin. Then, the mixture was heated on a water bath about 3o minutes at 80 ⁰ C.

The resulting mixture was transferred to a container through a filter (gausc? Filter). Then the solution was agitated with a mixer at high speed. 9 g of K-vinylcarbazole (B), 2 mg of methylene blue (C) and 3 mg of 4- (p-dimethylinostyryl) -quinolite as a sensitizer, dissolved in 6 cm of acetone, were added to this solution with stirring over a period of about 15 minutes.

Then 4 g of carbon tetrabromide, dissolved in 4 cm of acetone, were added after further stirring for 3 minutes,

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being an emulsion of uniformly dispersed combination ABC was obtained. The emulsion was applied to a sheet of baryta-coated paper as in Example 5. By drying the sheet for 80 seconds in a 100 ° C dryer, a photosensitive coating was obtained Sheet received.

A negative film was made with the photosensitive sheet in contact with a 500 W xenon lamp for 1/15 seconds exposed and then for 3 seconds with the light of a 5oo W WoIfram lamp with a wavelength over 55o nu, the was obtained by passing the light through a VO 55 filter, exposed. Then the sheet 60 thus exposed became Heated in a dryer at 100 ° C for seconds to develop the color of the exposed parts. The sheet thus obtained was allowed to stand under room light, the unexposed parts polymerizing and developing a white color.

It was assumed that originally yellowish 4- (p-dimethylaminostyryl) -quinoline and bluish methylene blue influenced the color formation. Actually appeared however, non-exposed parts are white-gray. The reflection density of the white parts of the image for blue light thus obtained were reduced to only 0.08 to 0.1 o.

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Example 9

- Example 8 was repeated with the difference that 4- (p-dimethylaminostyryl) -quinoline in an amount of 5 mg was used.

The obtained photosensitive sheet of baryta-coated paper was attached to the front surface of a cathode ray tube with an optical fiber surface at the front, i.e. a so-called optical fiber tube (optical fiber tube) brought into contact and exposed by means of a negative image.

The sheet exposed in this way was further exposed to the light of a 18o W low-pressure sodium lamp for a few seconds and then heated in a 100 ° C dryer for 60 seconds to give a positive image. The thus obtained Sheet was left to stand under room light, with unexposed parts of the sheet being polymerized and one gave a white part of the image with a reflection density of 0.08 to 0.1o for blue light.

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Claims (11)

Claims ί-Λ £ Photoeiapfindliche Mass., the {%) a pnotoenpfindliche disperse phase in the form of individual particles to the a combination of (H) an organic Halogenverbindang, upon exposure ait light of a suitable wavelength free Sadika-Ie or ion forms and the following allgeineine Formula feat: RCX ₃ in which R is an halogen atom, an alkyl group, an ary group, a halogen-substituted alkyl group or a halogen-substituted aryl group and X is a halogen atom / (B) one
U-vinyl compound, which has a vinyl group bonded directly to a nitrogen atom, and {€.) A third material which serves to color non-exposed parts in a white color -zxa
polymerize or fix, in (2) an aqueous dispersion medium in which this disperse phase is practically insoluble, the combination being so responsive to actinic light that an image of selective light absorption capabilities that is different from that of the Combination and the organic halogen compound, the N-Viny! Compound and des
third material, and which combination is polymerized to form a white color. 509809/0931 2. Photosensitive composition according to claim 1, characterized in that the organic halogen compound is carbon tetrabromide, hexachloroethane, pentabromoethane, iodoform, monobromotrichloromethane, o (, «', ^" - tribromotoluene or bromoform, 3. Photosensitive composition according to claim 1, characterized characterized in that the N-vinyl compound N-vinyl carbazole, N-vinylphenyl-Of-naphthylamine, N-vinyldiphenylamine, N-vinylindole, N-vinylphenylacetamide, N-vinylmethylacetamide, N-vinyldiglycolylimide, N-vinylphthalimide or K-vinylbenzthiazoline or N-vinylbenzotriazole. 4. Photosensitive composition according to claim 1, characterized characterized in that the material used is a vinyl compound, namely allyl chloride, vinyl acetate, methyl methacrylate, styrene, fluorostyrene, chloroprene, acrylonitrile, methyl vinyl ketone, Vinyl pyridine, a cyclic ether, maleic anhydride, acrylamide, isobutyl vinyl ether or p-vinyl diphenyl sulfide is. 5. Photosensitive composition according to claim 4, characterized characterized in that they contain the vinyl compound in a concentration of 0.04 to 4% by weight of the total amount of the organic Halogen compound and the N-vinyl compound. 509809/0931 6. Photosensitive composition according to claim 1, characterized characterized in that the third material is a dye, namely a thiazine dye or a cyanine dye. 7. Photosensitive composition according to claim 6, characterized characterized in that the thiazine dye is methylene green or methylene blue. 8. Photosensitive composition according to claim 6, characterized in that the cyanine dye 1,1'-diethyl-4,4'-carbocyanin iodide, 1,1'-diethyl-10-phenyl-2,2'-carbocyanine bromide, 3,3'-dinthyloxytricarbocyanine iodide, 1,1'-diethyl-2,2'-quinomonocarbocyanine iodide, 1,1'-diethyl-2,2'-quinodicarbocyanine iodide, 1,1'-diethyl-2,2'-quinotricarbocyanine iodide, 3,3'-diethylthiamonocarbocyanine iodide, 3,3'-diethylthiadicarbocyanine iodide, 3,3'-dimethyltricarbocyanine iodide, 3,3'-diethylselenamonocarbocyanine iodide, 3,3 · -Diethylselenadicarbocyaninjodid or Is 3,3'-diethylene selenate tricarbocyanine iodide. 9. Photosensitive composition according to claim 5, characterized in that it contains the dye in a concentration from 0.04 to 0.8% by weight of the total amount of the organic Contains halogen compound and the N-vinyl compound. 509809 / Ü931 10. Photosensitive composition according to claim 1, characterized characterized in that the organic halogen compound and the N-vinyl compound in a weight ratio in the range from To to 8o: 9o to 2o are present. 11. Photosensitive composition according to claim 1, characterized in that the dispersion medium gelatin, casein, Alginic acid, polyvinyl alcohol, an aqueous polyacrylic resin, Polyvinylpyrrolidone, an amine resin, an aldehyde resin or a cellulose derivative. 509809/0931