JPS6239422B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a method for producing two-component diazo imaging materials. Hitherto, two-component diazo image-forming materials, ie, diazo image-forming materials having a photosensitive layer on a support, the main components of which are a diazonium salt and a coupler that reacts with the diazonium salt, have been widely used. On the other hand, as a method for producing a two-component diazo image forming material, a polymer binder (e.g., cellulose diacetate, cellulose triacetate, cellulose butyrate, etc.) is dissolved in a low boiling point organic solvent (e.g., acetone, methyl acetate, etc.). onto a support (e.g. plastic film) (thickness, usually 50-100
μ), then heat it to a high temperature (usually around 100 to 200℃)
Under the impregnated receptor layer (thickness,
A method is known in which the impregnated receiving layer is impregnated with a photosensitive composition containing a photosensitive diazonium salt and dried. In this method, the coupler is contained in at least one of the photosensitive composition and the impregnated receiving layer. Industrially, drying at high temperatures for a long period of time is carried out while the support coated with the solution is conveyed by a large number of precisely controlled rolls. However, when forming an impregnated receptor layer by the above-mentioned conventional method, there are the following drawbacks. (a) It requires a large amount of heat energy because it is dried at high temperatures for a long time. (b) Requires equipment to handle organic solvents that evaporate in large quantities. (c) Requires large equipment space for drying. (d) Requires precise operational control of a large number of rolls. An object of the present invention is to provide a method for producing a two-component diazo image-forming material that eliminates the drawbacks of these conventional methods. The present invention relates to a compound that exhibits crosslinking properties when irradiated with high energy rays and a polymer compound that itself does not exhibit crosslinking properties when irradiated with high energy rays and is suitable for impregnating a photosensitive composition containing a photosensitive diazonium salt (hereinafter referred to as A liquid composition (hereinafter referred to as an irradiated liquid composition) containing a polymer compound for imparting impregnating properties (hereinafter referred to as an irradiated liquid composition) is coated in a layer on the surface of a flat support and cross-linked and cured by irradiation with high-energy rays. This is a method for producing a two-component diazo image forming material, which comprises impregnating the material with the photosensitive composition and drying the material. The planar support used in the present invention may be a support used in the production of conventionally known diazo image forming materials. For example, plastic film, which may be made of plastic film, synthetic paper, pulp paper, metal, glass, woven fabric, non-woven fabric, etc., has excellent physical strength, particularly dimensional stability, flatness, and transparency, such as biaxially oriented polyethylene terephthalate. Films are particularly preferred. The photosensitive diazonium salt may be a photosensitive diazonium salt used in the production of conventionally known diazo image forming materials, and the photosensitive diazonium salt is usually used in the form of a double salt with an inorganic halogen salt. . Examples of double salts include 1-diazo-4-
Examples include dimethylaminobenzene tetrafluoroborate, bis(1-diazo-3-methoxy-4-pyrrolidinobenzene) tetrachlorosincate, and the like. The types of couplers used in the present invention are also known and are selected with respect to the desired image hue. Particularly typical couplers are phenolic compounds and compounds with active methylene groups. Examples of phenolic compounds include resorcinol, bisresorcinol sulfide, catechol monohydroxyethyl ether, 2-hydroxynaphthalene-3-carboxylic acid-2'-methylanilide, and 2-hydroxynaphthalene-3-carboxylic acid ethanolamide. Examples of the compound having an active methylene group include acetanilide, acetoglycinamide, and 1,4-bis(acetoaceto)ethylenediamine. In the present invention, in order to prevent color development due to pre-coupling, it is desirable that the impregnated receiving layer and/or the photosensitive composition contain an auxiliary agent exhibiting acidity. In order to impregnate the photosensitive composition into the impregnation receiving layer, a conventionally known impregnation device, for example, an impregnation device comprising a liquid supply roll and a scraping member, can be used. After impregnating the photosensitive composition into the impregnated receptor layer, drying may be carried out under conventional drying conditions, usually at 60°C.
A temperature range of ~130℃ can be adopted. In the present invention, the impregnated receiving layer is crosslinked and cured by irradiating a liquid composition containing a compound exhibiting crosslinking properties and a polymer compound for imparting impregnating properties with high energy rays. The high-energy rays referred to in the present invention are particularly preferably ultraviolet rays or electron beams. As a light source for ultraviolet irradiation equipment, 200nm ~
Metal halide-mercury lamps, low-pressure, medium-pressure, high-pressure mercury lamps, etc. that emit ultraviolet light in the far-ultraviolet to near-ultraviolet ranges of 450 nm may be used. Typically, an electron beam irradiation device has an accelerating voltage of 100 to 600 KeV and a current value of 10 to 100 mA.
Use the one. Compounds that exhibit crosslinking properties upon irradiation with high-energy rays have already been sufficiently disclosed in the literature. In the present invention, those known materials may be used. Among these compounds, preferred are compounds that are liquid at room temperature and have 1 to 4 ethylenically unsaturated bonds but are not oligomers, or compounds that are liquid at room temperature and have 2 to 6 epoxy bonds. Among these preferred compounds, those having a boiling point of 100°C or higher are particularly preferred. Among compounds that have 1 to 4 ethylenically unsaturated bonds but are not oligomers and are liquid at room temperature, examples of monomers having only one ethylenically unsaturated bond include methyl acrylate, 2-ethylhexyl acrylate, and 2-ethylhexyl acrylate. -Hydroxyethyl acrylate, tetrahydrofurfuryl acrylate, phenoxyethyl acrylate or their methacrylates, as well as styrene, N-vinylpyrrolidone and the like. Examples of compounds that have 2 to 4 ethylenically unsaturated bonds but are not oligomers and are liquid at room temperature include ethylene glycol diacrylate, propylene glycol diacrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate, and penta Examples include erythritol pentaacrylate and their methacrylates. Examples of compounds that have 2 to 6 epoxy bonds and are liquid at room temperature include the following. Examples include 1,6-hexanediol diglycidyl ether, glycerin triglycidyl ether, bisresorcinol tetraglycidyl ether, and epoxy novolak (epoxy equivalent: 172 to 181). As the polymer compound for imparting impregnating properties, cellulose derivatives are particularly preferred, but vinyl polymers, formalin cocondensation resins, etc. may also be used. Among these, it is particularly preferable to select a cellulose derivative that satisfies compatibility. Examples of cellulose derivatives include the following. (a) Alkyl ester derivatives obtained by modifying cellulose with fatty acids, such as cellulose acetate, cellulose acetate butyrate, cellulose acetate isobutyrate, cellulose acetate propionate, (b) esters obtained by modifying cellulose with nitric acid. Derivatives such as cellulose nitrate, (c) ether derivatives obtained by modifying cellulose with dialkyl sulfate or alkyl halides, such as ethyl cellulose and propyl cellulose. The impregnating polymer compound used in the present invention is essential for impregnating the impregnated receiving layer with a photosensitive composition containing a photosensitive diazonium salt. In addition, the polymer compound enables alkaline compounds such as ammonia gas to be rapidly exhausted into the impregnated receiving layer of the exposed diazo imaging material, allowing development processing to be carried out in a short time. This provides a practical advantage. In carrying out the present invention, the molar ratio of coupler to diazonium salt is usually 0.2 to 8, preferably 0.5 to 3.5. The total weight of the diazonium salt and coupler is 5% of the weight of the impregnated receptor layer.
-50% is preferred, particularly preferably 10-40%. When the liquid composition to be irradiated contains a liquid compound that has 1 to 4 ethylenically unsaturated bonds but is not an oligomer, the weight ratio of the polymer compound for imparting impregnating properties to the compound that exhibits crosslinking properties by high-energy rays. is preferably 20 to 80%, particularly preferably 35 to 68%. When containing a liquid compound having 2 to 6 epoxy bonds, the weight ratio is preferably 10 to 90%, particularly preferably 30 to 70%.
%. When carrying out the present invention in an embodiment in which a liquid composition to be irradiated containing a liquid compound having 1 to 4 ethylenically unsaturated bonds but not an oligomer is irradiated with ultraviolet rays, photocrosslinking that generates radicals by ultraviolet irradiation is required. Preference is given to using activators. Examples of such photocrosslinking activators include benzoin, benzoin methyl ether, benzophenone, and benzyl. When carrying out the present invention in an embodiment in which a liquid composition to be irradiated containing a liquid compound having 2 to 6 epoxy bonds is irradiated with ultraviolet rays, Lewis
Using a photocrosslinking activator that generates an acid can
Practically advantageous. Suitable photocrosslinking activators that generate such Lewis acids are described, for example, in U.S. Pat.
No. 3936557, Special Publication No. 14277, Special Publication No. 14277, Special Publication No. 14277
−14278, Special Publication No. 14279, Special Publication No. 14279, No. 14279, Japanese Patent Publication No. 14279
It is disclosed in No. 30402, etc. For liquid compositions to be irradiated containing liquid compounds having 1 to 4 ethylenically unsaturated bonds but not oligomers, a small amount of a thermal polymerization inhibitor is added in order to prevent gelation during storage of the liquid composition to be irradiated. It is preferable to add. Examples of thermal polymerization inhibitors include hydroquinone, hydroquinone methyl ether, 2,
Examples include 6-di-tert-butyl-p-cresol and Kyuperon. However, copper salts, which are commonly used as thermal polymerization inhibitors, cannot be used because they accelerate the decomposition of diazonium salts. When using a liquid composition to be irradiated containing a liquid compound having 1 to 4 ethylenically unsaturated bonds but not an oligomer, the composition contains a crosslinked compound having 2 or more ethylenically unsaturated bonds. Preference is given to using oligomers. The crosslinkable oligomer preferably has one to four ethylenically unsaturated bonds, but is compatible with a liquid compound that is not an oligomer. Generally, those having a molecular weight of about 300 or more and 3000 or less are advantageously used. Examples of crosslinkable oligomers include polyester acrylate or polyester methacrylate obtained using low molecular weight polyester, epoxy acrylate, epoxy methacrylate, urethane acrylate, urethane methacrylate,
etc. The two-component diazo image forming material of the present invention may contain conventional stabilizers such as acidic components such as 5-sulfosalicylic acid and succinic acid, inorganic salts such as zinc chloride, and 2,7-naphthalene disulfonic acid. It may contain alkali salts of sulfonic acids such as disodium, thioureas such as thiourea or diethylthiourea. Furthermore, insoluble powders such as colloidal silica, powdered barium sulfate, and clay may also be present. When using a liquid composition to be irradiated containing a liquid compound having 2 to 6 epoxy bonds, it is preferable to include a low molecular weight liquid compound having one epoxy bond as a diluent in the composition. Examples of such diluents include styrene oxide, phenyl glycidyl ether, etc., which are known as diluents for ordinary epoxy resins, as well as glycidyl methacrylate and allyl glycidyl having one epoxy bond and one ethylenically unsaturated bond. There is ether etc. According to the present invention described in detail above, the drawbacks of the conventional methods described above are overcome, and therefore a two-component diazo image-forming material can be industrially advantageously produced. Two-component diazo image-forming materials, after contact exposure with the original image, can be easily exposed to ammonia containing water vapor at normal pressure or alkaline compounds such as high-pressure anhydrous ammonia gas that form an azo dye through the reaction of a diazonium salt and a coupler component. Developed by contacting for a period of time. Light sources for contact exposure of the above-mentioned two-component diazo image forming materials include chemical lamps that emit ultraviolet light in the 300 to 450 nm region, medium pressure, high pressure, and ultra-high pressure mercury lamps, metal hydrad-mercury lamps, and carbon arcs. Lights are used. It is convenient to use commercially available equipment for exposure and development of the two-component diazo image forming material. Examples are shown below. In the examples, "part" means part by weight (Kg), and "capacity" means volume (). Example 1 Synthesis Example 1 [Synthesis of polyester acrylate] Isophthalic acid 83 parts Diethylene glycol 106 parts Adipic acid 146 parts p-Toluenesulfonic acid (catalyst) 2.5 parts The above mixture was reacted at 120°C, and the acid value was 130~
When the temperature reached 150, 116 parts of 2-hydroxyethyl acrylate and 0.45 parts of hydroquinone monomethyl ether (thermal polymerization inhibitor) were added, air was blown into the mixture, and the reaction was carried out at 120°C for 4 hours to obtain polyester acrylate. Next, a liquid composition to be irradiated consisting of the following components was prepared. 2-Hydroxyethyl acrylate (crosslinking agent)
50 parts of the above polyester acrylate (crosslinkable oligomer) 12 parts Cellulose acetate butyrate 1/2 second (polymer compound for imparting impregnating properties) (manufactured by Kodatsu, USA)
CAB381-2) 15 parts cellulose butyrate 1/2 sec (same as above) (same as above HSB) 5 parts poly(methyl methacrylate-ethyl methacrylate) (same as above) (Acryloid B72 manufactured by Rohm & Haas, USA) 4 parts benzoin isopropyl ether ( Photocrosslinking activator) 3 parts The viscosity of the above composition was 1350 cps (25°C) (using a B-type viscometer. Measurements were also made using the same type of viscometer in the following examples). The coating was applied using a coater to a biaxially stretched polyethylene terephthalate film (Merinex #542, manufactured by ICI, UK), which was coated with an ultraviolet irradiation device (metal halide-mercury lamp, manufactured by Iwasaki Electric, 80 W/cm, at a running speed of 20 m/min). An impregnated receptor layer with a film thickness of approximately 6.5 μm was created by passing through the impregnated receptor layer (using 3 tubes). Next, a two-component diazo photosensitive composition solution consisting of the following components was prepared. 1-Diazo-2.5-diethoxythiomorpholinobenzene tetrafluoroporate (diazonium salt) 10 parts acetoacetanilide (Kuplar) 6 parts 2-hydroxynaphthalene-3-carboxylic acid
2'-methylanilide (same as above) 18 parts stannous chloride (metal salt for accelerating development) 2.5 parts tartaric acid (early coupling inhibitor) 3.5 parts thiourea (reducing agent) 0.8 parts acetone 700 volumes The photosensitive composition solution Impregnate the impregnated receptor layer on the film at a running speed of 20 m/min using a kiss coater and a wire bar "scraper" at 50 to 80°C.
A two-component diazo image-forming material was obtained by drying at a temperature of 1,000 yen through a simple vertical dryer with few supporting rolls. The two-component diazo image-forming material was subjected to exposure and ammonia development tests, as well as tests on the developed material, and the results shown in Table 1 were obtained.

[Table] Sensitivity in Table 1 was evaluated as 1, 2, 3, or 4 for high, equal, and low sensitivity in comparison with equivalent products manufactured by conventional methods. Specifically, after baking Kodatsu Step Tablet No. 3, we checked the number of steps that became transparent by developing it with ammonia, and if it was transparent up to 4 steps, it was 1 or 3.
The rating was 2 if the level was transparent, and the rating was 3 or 4 if the level was 2 or less transparent. The surface hardness of the developed material was expressed by pencil hardness. Adhesiveness was determined in accordance with JISD-0202 using a so-called board test. In other words, make 100 squares (10 x 10) with a side of 1 mm on the surface of the developed material using a razor blade.
The cellophane tape was then pressed onto the squares, rapidly peeled off, and the number of squares remaining on the surface of the material was displayed. Therefore, 100/100 indicates that all 100 squares were not peeled off. To test for brittleness, press the developed material firmly with both hands.
1. If there is no peeling of the film at all, 2. If there is a very thin line peeling, 2. If there is a line of 1 cm or more or surface peeling with an area of about 4 mm ^2. 3. If there is a significant peeling defect. Some were given a 4.
Developability was determined using a commercially available ammonia developing device at developing speeds of 15 m/min, 12 m/min, 18 m/min, and 5 m/min.
The minutes were 1, 2, 3, and 4, respectively. The developability of an equivalent diazo image forming material prepared by the conventional method is 2. Bleeding means that one part of the developed material
This refers to the fact that the azo dye in the color development area bleeds out when it is placed in an environment with relatively high humidity changes for a period of about several months. A rating of 1 was given when there was no bleeding, a rating of 2 was given where a slight amount of bleeding occurred but it was comparable to that of a commercially available diazo image forming material, and a rating of 3 was given where there was considerable bleeding. Blooming refers to the development in which when an oily substance adheres to the image area of a developed material, the dye in the adhered area stands out.For example, when touched with a dirty fingertip, a fingerprint-like bloom tends to appear. In the bloom resistance test, the image area was strongly pressed with a fingertip, placed in a drying device at 80°C, and the occurrence of bloom was examined after a certain period of time.
5-8 hours, 4-5 hours, 2-3 hours and 1-
If bloom occurs after 2 hours,
Rated 1, 2, 3, and 4. The bloom resistance rating of the equivalent product using the conventional method is 2. The above evaluation method is the same in the following examples unless otherwise specified. As seen in the above explanation, the score evaluation is based on the evaluation 2 of the diazo image forming material produced by the conventional method. Example 2 Synthesis Example 2 [Synthesis of urethanized epoxy acrylate] Urethane epoxy resin (EPU made by Asahi Denka)
10) 68 parts acrylic acid 14.4 parts triethylbenzylammonium chloride (catalyst) 0.5 parts trimethylolpropane triacrylate (reaction diluent and crosslinking agent) 55 parts hydroquinone monomethyl ether (thermal polymerization inhibitor) 0.14 parts Dry air was blown into the above mixture. while 100℃
The mixture was reacted for 6 hours to obtain a trimethylolpropane triacrylate solution of urethanized epoxy acrylate. Next, a liquid composition to be irradiated consisting of the following components was prepared. 2-Hydroxypropyl acrylate (crosslinking agent) 35 parts Trimethylolpropane acrylate (crosslinking agent) solution of the urethanized epoxy acrylate (crosslinkable oligomer) of Synthesis Example 2 13 parts Ketone resin (polymer compound for imparting impregnation properties) (Hitachi Chemical) HIRAKU 111) 10 parts Cellulose acetate butyrate (polymer compound for imparting impregnating properties) CAB551 manufactured by Kodatsu, USA
0.2) 33 parts benzoin ethyl ether (photocrosslinking activator)
4 parts Add the following auxiliaries for a two-component diazo image forming material to the liquid composition to be irradiated to make a uniform composition [viscosity 1750 cps (25°C)] Micronized disodium 2,7-naphthalene sulfonate (Development accelerator) 5.2 parts Tartaric acid (early coupling prevention agent) 4.7 parts Thiourea (reducing agent) 11 parts
A μm biaxially stretched polyethylene terephthalate film was coated using the same equipment as in Example 1 and irradiated with ultraviolet rays to form an impregnated receptor layer (film thickness approximately 6 μm).
In this case, the coated mixed composition was heated to 60°C and extruded from an extruder, and the film running speed was 23 m/min. Next, a two-component diazo photosensitive composition solution consisting of the following components was prepared. 1-Diazo-2,5-dibutoxymorpholinobenzene tetrafluoroborate (diazonium salt) 10.5 parts 2-hydroxynaphthalene-3-carboxylic acid
2′-Methylanilide (azo coupling component)
19 parts Zinc chloride (diazo stabilizer and development accelerator) 7 parts Acetone 500 volumes Methyl cellosolve 200 volumes The photosensitive composition solution was impregnated in the same apparatus as in Example 1 and dried to form a two-component diazo image forming material. Obtained. The upper limit of the drying temperature in this case was set at 120°C, and the running speed was the same as above, 23 m/min. The test results for the two-component diazo image forming material were as shown in Table 2.

[Table] Example 3 A liquid composition to be irradiated consisting of the following components was prepared. Phenyl glycidyl ether (crosslinking agent) 19 parts glycidyl methacrylate (same as above) 52 parts glycerin triglycidyl ether (same as above)
23 parts cellulose acetate butyrate (polymer compound for impregnating properties) (CAB551 manufactured by Kodatsu, USA)
-0.01) 30 parts ethylhydroxyethylcellulose (same as above)
(EHEC-Low, manufactured by Hercules, USA) 13 parts The above composition [viscosity 860 cps (25°C)] was applied to a 75 μm biaxially stretched polyethylene terephthalate film that had been subjected to undercoating treatment, and at an accelerating voltage of 300 KeV and a current value of 100 mA, approximately 1.5 Mrad was applied. It was cured by electron beam irradiation at a radiation absorption amount to form an impregnated receptor layer with a film thickness of about 8 μm. Next, a two-component diazo photosensitive composition having the following composition was prepared. Bis(1-diazo-3-methyl-4-pyrrolidinobenzene)tetrachlordine kecate (diazonium salt) 6 parts 2-hydroxynaphthalene-3-carboxylic acid-
3'-N-morpholinopropylamide (azo coupling component) 9.5 parts Citric acid (early coupling inhibitor) 8 parts Disodium 2,7-naphthalene disulfonate (development accelerator) 3 parts Thiourea (reducing agent) 7.5 parts Methyl cellosolve acetate 200 volumes Acetonitrile 70 volumes Dioxane 130 volumes The photosensitive composition solution was applied using a wire bar coater to impregnate the impregnated receiving layer and dried at 80 to 120°C, 2
A component-based image forming material was obtained, and the test results shown in Table 3 were obtained.

[Table] Examples 4 to 14 Synthesis Example 3 [Synthesis of urethane acrylate] Tolylene diisocyanate (2,4-disubstituted product/
2,6-disubstituted product = 80/20) 174 parts triethylene glycol 75 parts 1,6-hexanediol diacrylate
200 parts Hydroquinone monomethyl ether 0.57 parts The above mixture was reacted at 60°C for 4 hours while blowing air to synthesize a prepolymer having isocyanate groups at both ends of the resulting polymer, and further 116 parts of 2-hydroxyethyl acrylate was added. ℃
The mixture was reacted for 6 hours to obtain urethane acrylate.
Note that 1,6-hexanediol diacrylate in the above reaction mixture is used as a diluent in the polyaddition reaction, but since it also serves as a crosslinking agent, the mixture is directly impregnated as part of the composition forming the receptor layer. It can be used as a part. Synthesis Example 4 [Synthesis of epoxy acrylate] Epoxy resin (Ciel Chemical Epicote 828;
Epoxy equivalent: 185-192) 94.5 parts Acrylic acid 36 parts N,N-dimethylaniline (catalyst) 1.3 parts The above mixture was reacted by blowing air at 100°C to obtain epoxy acrylate. The various irradiated liquid compositions shown in Table 4 were prepared, applied and cured in the same manner as in Example 1, and an impregnated receiving layer was formed on each of the 75 μm biaxially stretched polyethylene terephthalate films that had been subjected to subbing treatment. An evaluation test was conducted on a two-component diazo image forming material obtained by impregnating it with a photosensitive composition. The film running speed for forming the impregnated receptor layer is
The film running speed during the impregnation step is 30 to 80 m/min.

[Table] Table 4 The abbreviations of each component are as follows. Crosslinking agent C ₁ 2-hydroxyethyl acrylate C ₂ 2-hydroxypropyl acrylate C ₃ Tetrahydrofurfuryl acrylate C ₄ Ethylene glycol monoacrylate C ₅ Ethyl crotonate C ₆ Cyclohexyl acrylate C ₇ 2-Ethylhexyl acrylate C ₈ 1,6-hexane Diol diacrylate C ₉ Phenoquinoethyl acrylate C ₁₀ N-vinylpyrrolidone crosslinkable oligomer Q ₁ Epoxy acrylate (synthesized product of Synthesis Example 4) Q ₂ Urethane acrylate (synthesized product of Synthesis Example 3, 1,6-hexane diol diacrylate Acrylate solution) Q _3Urethanized epoxy acrylate (Synthesis 2, trimethylolpropane triacrylate solution) Polymer compound for imparting impregnating properties P _1Cellulose acetate butyrate 1/2 second (CAB381-2 manufactured by Kodatsu, USA) P ₂ Poly(methyl methacrylate ethyl methacrylate) (manufactured by Rohm and Haas, USA)
Acryloid-B72) P ₃ poly(methyl acrylate-methyl methacrylate) (manufactured by Rohm and Haas, USA)
Acryloid-101) P ₄ xylene resin (Mitsubishi Gas Chemical Co., Ltd., Nicanol L) P ₅ Ketone resin (Hitachi Chemical Co., Ltd., Hilux
111) P ₆ ketone resin (Kunstharz, Bayer, Germany)
AFS) Photocrosslinking activator S ₁ Benzoin ethyl ether S ₂ Benzyl S ₃ Benzoin isopropyl ether S ₄ Benzophenone S ₅ 2-tert-butylanthraquinone thermal polymerization inhibitor i ₁ Hydroquinone monomethyl ether i ₂ 2,6-di-tert-butyl- p-Cresol The number before the above symbol in the table indicates parts by weight. For example, 37C ₉ means adding 37 parts of crosslinking agent C ₉ . However, for polymerization inhibitors, the unit is ppm. Examples 15-19 The two-component diazo image forming material prepared in Example 2 was treated with different combinations of some diazonium salt and coupler components in the impregnated receiving layer on a 28 μm biaxially oriented polyethylene terephthalate film containing auxiliaries. Test results regarding image forming materials obtained by impregnating two-component diazo photosensitive compositions are shown below.
This is summarized in 5. However, when preparing the photosensitive composition solution, the amount of zinc chloride added and the type and amount of solvent added were the same as in Example 2 for comparative study.

[Table] The abbreviations for each component in Table 5 are as follows. Diazonium salt d ₁ bis(1-diazo-3-methoxy-4-pyrrolidinobenzene) tetrachlorzincate d _{2 1} -diazo-4-N,N-dimethylaminobenzene tetrafluoroborate azo coupling component a ₁ 2- Hydroxynaphthalene-3-carboxylic acid-
2'-Methylanilide a ₂ Bis(2,4-dihydroxyphenyl) sulfide a ₃ Acetoacetobenzylamide The number before the symbol in the table indicates parts by weight. for example
_15a3 means adding 15 parts of azo coupling component _a3 .

Claims (1)

[Scope of Claims] 1. A compound that exhibits crosslinking properties when irradiated with high energy rays and a polymer that itself does not exhibit crosslinking properties when irradiated with high energy rays and is suitable for impregnating a photosensitive composition containing a photosensitive diazonium salt. A liquid composition containing the compound is applied onto the surface of a planar support, and then the liquid composition is crosslinked and cured by irradiation with high energy rays to form an impregnated receiving layer, and the photosensitive composition is applied to this. A method for producing a two-component diazo image forming material, which comprises impregnating and drying the material. 2. The method according to claim 1, wherein the compound exhibiting crosslinking properties upon irradiation with high-energy rays is a liquid compound having 1 to 4 ethylenically unsaturated bonds but not an oligomer. 3. The method according to claim 1, wherein the compound exhibiting crosslinking properties upon irradiation with high energy rays is a liquid compound having 2 to 6 epoxy bonds. 4. The method according to claim 1, wherein the polymer compound that does not exhibit crosslinking properties upon irradiation with high-energy rays and is suitable for impregnating a photosensitive composition containing a photosensitive diazonium salt is a cellulose derivative. 5. According to any one of claims 1 to 4, in which the coupler component is mixed into either a photosensitive composition containing a diazonium salt or a liquid composition coated on the surface of a planar support. the method of.