JPH0431104B2 - - Google Patents

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention relates to a photosensitive composition suitable for producing lithographic printing plates. More specifically, the present invention relates to a photosensitive composition containing an O-quinonediazide compound as a photosensitive component. [Prior Art] It is known that when an O-quinonediazide compound is irradiated with actinic rays, it decomposes to produce a five-membered ring carboxylic acid, which becomes soluble in alkaline water. Therefore,
Photosensitive compositions containing O-quinonediazide compounds have been widely used for lithographic printing plates, photoresists, and the like as photosensitive compositions for producing positive-positive images. These diazo compounds generally have an O-
It is applied in the form of sulfonic acid esters obtained by condensing quinonediazide compounds with mono- or polyhydroxyphenyl compounds. Examples of hydroxyphenyl compounds that are condensation partners for O-quinonediazide compounds include 2,2'-dihydroxy-diphenyl, 2,2',4,4'-tetrahydroxydiphenyl, 2,3-dihydroxynaphthalene, p -t-butylphenol, etc., and there are many other examples. Among them, U.S. Patent No.
Phenol described in specification No. 3046120
Formaldehyde resin or O-cresol-
Relatively high molecular weight O such as O-naphthoquinonediazide sulfonic acid ester of formaldehyde resin
- Quinonediazide compounds are excellent in film-forming properties and have been widely used. Furthermore, the condensation polymerization product of pyrogallol and acetone described in Japanese Patent Publication No. 43-28403 has not only excellent film-forming properties but also excellent sensitivity and developability, and has been widely used. Examples of the sulfonyl chloride compound of O-quinonediazide include 1,2-naphthoquinone-2-
Diazide-4-sulfonyl chloride, 1,2-
Examples include naphthoquinone-2-diazido-5-sulfonyl chloride, and 1,2-naphthoquinone-2-diazido-5-sulfonyl chloride has been widely used. However, 1 of polyhydroxyphenyl obtained by condensation polymerization of acetone and pyrogallol,
When 2-naphthoquinone-2-diazide-5-sulfonyl chloride ester is used as a photosensitive composition, it has the disadvantage that it is exposed to light in a relatively short period of time when irradiated with a fluorescent lamp, and fogging is likely to occur. For example, when using this photosensitive composition in a lithographic printing plate, after accurately overlapping marks written at predetermined positions on the lithographic printing plate (hereinafter referred to as registration marks) with registration marks on the original film, the exposure light source is However, in order to accurately determine the printing position, the registration marks are drawn thinly, so sufficient lighting is required to identify and align the registration marks accurately. It is difficult to sufficiently identify dragonflies under the yellow safety lights commonly used for lighting in workplaces, so fluorescent lights are often used. Therefore, being easily exposed to fluorescent light means that the register mark alignment work must be completed quickly. Furthermore,
It is often necessary to print the original film on a single lithographic printing plate many times at different locations, and it takes time and effort to shield areas other than the area where the original film is to be printed. Furthermore, when 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride ester of polyhydroxyphenyl obtained by polycondensation of acetone and pyrogallol is used as a photosensitive composition, no fogging occurs due to fluorescent light. However, it has the drawbacks of low sensitivity, poor stability over time, and poor printout properties. On the other hand, the sensitivity to the exposure light source of a lithographic printing plate using a photosensitive composition containing 1,2-naphthoquinone-2-diazide-5-sulfonic acid ester of polyhydroxyphenyl obtained by condensation polymerization of acetone and pyrogallol was reduced. It is known that if this is done, the fog against fluorescent lights will also be reduced. However, lowering such sensitivity not only requires a long time for exposure and reduces work efficiency, but also increases power consumption, which is undesirable. In addition, 1,2-naphthoquinone-2 of the above polyhydroxyphenyl
If the amount of the diazo compound in the photosensitive composition is decreased in order to increase the sensitivity of a lithographic printing plate using -diazide-4-sulfonic acid ester in the photosensitive composition, the development latitude also decreases, which is undesirable.
Furthermore, 1,2-naphthoquinone-2-diazide-5-sulfonic acid ester (A) of polyhydroxyphenyl obtained by condensation polymerization of acetone and pyrogallol, and 1,2-
A lithographic printing plate using a mixture of naphthoquinone-2-diazide-4-sulfonic acid ester (B) in a photosensitive composition is also known (Japanese Patent Publication No. 46-42448).
However, even if the mixing ratio of A and B is changed, the following performance is exhibited and the object of the present invention cannot be achieved. That is, when either A or B is extremely large, the performance is close to that when A or B is used alone; on the other hand, for example, when A/B = 1/1
When a mixture of (molar ratio) is used, fog caused by a fluorescent lamp is slightly reduced, but at the same time, sensitivity, stability over time, and print-out properties are also reduced, which is not preferable. [Object of the Invention] Accordingly, an object of the present invention is to provide a photosensitive composition that is resistant to fogging when exposed to a fluorescent lamp and has excellent sensitivity, development latitude, stability over time, and printout properties. [Structure of the Invention] As a result of various studies to achieve the above object, the present inventors have discovered that polyhydroxyphenyl compounds,
By incorporating a product obtained by condensing both 1,2-naphthoquinone-2-diazide-5-sulfonyl halide and 1,2-naphthoquinone-2-diazide-4-sulfonyl halide into the photosensitive composition. The inventors have discovered that the above object can be achieved, and have completed the present invention. That is, the present invention adds 1,2-naphthoquinone-2-diazide to a polyhydroxyphenyl compound.
This is a photosensitive composition characterized by containing a product obtained by condensing both 5-sulfonyl halide and 1,2-naphthoquinone-2-diazide-4-sulfonyl halide. The polyhydroxyphenyl compounds used in the present invention are the condensates of pyrogallol and acetone described in US Pat. No. 3,635,709, and the condensates of acetone described in US Pat. No. 4,028,111. Polyesters with hydroxyl groups at the ends, p-
Homopolymers of hydroxystyrene or copolymers thereof with other copolymerizable monomers, p-
Copolymers of aminostyrene and other copolymerizable monomers, phenol-formaldehyde resins or cresol-formaldehyde resins described in US Pat. No. 3,046,120, and the like.
In particular, when a condensate of pyrogallol and acetone is used, a photosensitive composition with excellent sensitivity and development latitude can be obtained. In the present invention, 1,2-naphthoquinone-2-diazide-5-sulfonyl halide () and 1,2-
The molar ratio of naphthoquinone-2-diazide-4-sulfonyl halide () is /=2/8 to 8/
A range of 2 is preferred. If the proportion of compound () increases beyond this range, the sensitivity and stability over time of the resulting photosensitive composition will decrease, and if it decreases beyond this range, the fluorescence lamp stability of the resulting photosensitive composition will decrease. There is a tendency for the performance to decrease, which is undesirable. A more preferable range of the above molar ratio is /
=3/7 to 7/3. The photosensitive composition of the present invention contains, as a photosensitive component, other O-quinonediazide compounds in addition to the condensates of the polyhydroxyphenyl compound and compounds () and () of the present invention. be able to. As such known O-naphthoquinone diazide compounds, there are
Most preferred is the ester of 1,2-naphthoquinone-2-diazide-5-sulfonyl chloride and pyrogallol-acetone resin described in Japanese Patent No. 28403. Other suitable known orthoquinone diazide compounds include U.S. Pat.
1,2-naphthoquinone-2-diazide described in No. 3046120 and No. 3188210
There are esters of 5-sulfonyl chloride and phenol-formaldehyde resins. Other known O-naphthoquinonediazide compounds that can be used in the present invention include JP-A-47-5303 and JP-A-48-5303.
No. 63802, No. 63803, No. 96575,
No. 49-38701, No. 13354 (1973), Special Publication No. 41-1973
Publications such as No. 11222, No. 45-9610, and No. 17481, US Pat. No. 2797213, US Pat. No. 3454400, US Pat.
British Patent No. 3785825, British Patent No. 1227602, British Patent No.
Examples include those described in the specifications of German Patent No. 1251345, German Patent No. 1267005, German Patent No. 1329888, German Patent No. 1330932, and German Patent No. 854890. The total amount of the O-quinonediazide compound in the photosensitive composition of the present invention is 5 to 80% by weight, more preferably 20 to 80% by weight, including the known compound and the O-quinonediazide compound in the present invention.
40% by weight is suitable. Further, the proportion of the condensate of the polyhydroxyphenyl compound and the compound () and () in the present invention in the photosensitive composition of the present invention is
-25~ based on the amount of quinonediazide compound
A suitable amount is 100% by weight, more preferably 50 to 100% by weight. In the specification of the present invention, phenol formaldehyde resin, cresol formaldehyde resin,
Phenol-modified xylene resin, polyhydroxystyrene, polyhalogenated hydroxystyrene, etc.
A known alkali-soluble polymer compound can be contained. The alkali-soluble polymer compound is used in an amount of 70% by weight or less, more preferably 50 to 70% by weight of the total composition. The composition of the present invention may contain a cyclic acid anhydride to increase sensitivity, a print-out agent to obtain developable image immediately after exposure, a dye as an image coloring agent, and other fillers. Examples of the cyclic acid anhydride include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, 3,6-endooxy- ^Δ4 -tetrahydrophthalic anhydride, and tetrachloro as described in US Pat. No. 4,115,128. Phthalic anhydride, maleic anhydride, chloromaleic anhydride, α-phenyl maleic anhydride,
Examples include succinic anhydride and pyromellitic acid. By containing these cyclic anhydrides in an amount of 1 to 15% by weight based on the total composition, sensitivity can be increased up to three times. Typical print-out agents for obtaining a visible image immediately after exposure include a combination of a photosensitive compound that releases an acid upon exposure and an organic dye that can form a salt. Specifically, Tokukai Sho
Combinations of O-naphthoquinonediazide-4-sulfonic acid halide and salt-forming organic dyes described in JP-A-50-36209 and JP-A-53-8128; Examples include the combination of a trihalomethyl compound and a salt-forming organic dye described in Japanese Patent No. 54-74728. In addition to the above-mentioned salt-forming organic dyes, other dyes can also be used as image coloring agents. Suitable dyes include oil-soluble dyes and basic dyes, including salt-forming organic dyes. Specifically, oil yellow #101, oil yellow #130, oil pink #312, oil green BG, oil blue
BOS, Oil Blue #603, Oil Black BY,
Oil Black BS, Oil Black T-505 (manufactured by Orient Chemical Industry Co., Ltd.) Crystal Violet (C142555), Methyl Violet (C142535), Rhodamine B (C145170B), Malachite Green (C142000), Methylene Blue (C152015), etc. can be given. The composition of the present invention is applied onto a support after being dissolved in a solvent that dissolves each of the above components. Solvents used here include ethylene dichloride, cyclohexanone, methyl ethyl ketone, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, 2-methoxyethyl acetate, toluene, and ethyl acetate, and these solvents can be used alone or in combination. do. The concentration (solid content) of the above components is suitably 2 to 50% by weight. Also, the amount of application varies depending on the application, but
For example, for photosensitive planographic printing plates, the solid content is generally preferably 0.5 to 3.0 g/m ² . As the coating amount decreases, the photosensitivity increases, but the physical properties of the photosensitive film deteriorate. When producing a lithographic printing plate using the photosensitive composition of the present invention, the support may be a hydrophilized aluminum plate, such as a silicate-treated aluminum plate, an anodized aluminum plate, a grained aluminum plate, or a silicate plate. There are coated aluminum plates, zinc plates, stainless steel plates, chrome-treated steel plates, hydrophilized plastic films and paper. Examples of developing solutions for the photosensitive composition of the present invention include sodium silicate, potassium silicate, sodium hydroxide, potassium hydroxide, lithium hydroxide, tribasic sodium phosphate, dibasic sodium phosphate, tribasic ammonium phosphate, ammonium diphosphate,
Aqueous solutions of inorganic alkaline agents such as sodium metasilicate, sodium bicarbonate, aqueous ammonia, etc. are suitable and are added at a concentration of 0.1 to 10% by weight, preferably 0.5 to 5% by weight. Moreover, a surfactant and an organic solvent such as alcohol can be added to the alkaline aqueous solution as required. [Effects of the Invention] According to the present invention, a photosensitive composition is provided which has excellent sensitivity, development latitude, stability over time, and printout property, and is less likely to cause fogging due to fluorescent lamps, compared to conventional photosensitive compositions. You can get things. [Example] Next, the present invention will be explained in more detail by giving Examples and Synthesis Examples. Note that all percentages in the following Examples and Synthesis Examples are by weight unless otherwise specified. Synthesis example 1 Dissolve 100g of pyrogallol in 800ml of acetone,
Add 12g of phosphorus oxychloride to this as a condensation catalyst,
Stirred at room temperature for 3 days. Thereafter, the reaction mixture was poured into cold water 7 with stirring, and the precipitated light brown polyhydroxyphenyl resin was separated and dried to obtain 160 g. VPO (Vapor Pressure)
The number average molecular weight of this resin was measured using an osmometer (vapor pressure osmometer) and found to be 1,680. Dissolve 50g of the above resin in 360ml of methyl ethyl ketone/dimethylformamide (DMF) (5/1),
It was added to a separately prepared 240 ml solution of 20 g of 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride in methyl ethyl ketone/DMF (5/1). After stirring at room temperature for 1 hour, 7.5 g of triethylamine was added dropwise, and 20 ml of water was further added, and the pH of the reaction system was adjusted to 6.0 to 6.5 with triethylamine. This reaction system solution was poured into cold water 5 with stirring, and after separating the precipitated brown precipitate, it was dried under reduced pressure at room temperature. The yield was 65g. The 1,2-naphthoquinone-2- thus obtained
The diazide-4-sulfonic acid ester compound was dissolved again in 300 ml of methyl ethyl ketone, and 1,
A solution of 33 g of 2-naphthoquinone-2-diazide-5-sulfonyl chloride in 300 ml of methyl ethyl ketone was added. After stirring at room temperature for 1 hour, 12.4 g of triethylamine was added dropwise. After adding another 20ml of water, adjust the pH of the reaction system to 6.0~6.0 with triethylamine.
Adjusted to 6.5. This reaction solution was poured into cold water 5 with stirring, and the yellow brown precipitate that had precipitated was collected. After purification by reprecipitation, 88 g was obtained as a result of drying at room temperature under reduced pressure. As a result of UV spectrum analysis, it was found that the 1,2-naphthoquinone-2-diazide-4-sulfonyl group and the 1,2-naphthoquinone-2-diazide-4-sulfonyl group in this resin
The contents of 2-naphthoquinone-2-diazido-5-sulfonyl groups were 20 mol% and 24 mol%, respectively, per resin unit skeleton. Synthesis Example 2 50g of polyhydroxyphenyl resin obtained from pyrogallol and acetone obtained in Synthesis Example 1 was dissolved in 360ml of methyl ethyl ketone/DMF (5/1), and 1,2-naphthoquinone-2-diazide prepared separately was dissolved.
A solution of 30.2 g of 4-sulfonyl chloride in 240 ml of methyl ethyl ketone/DMF (5/1) was added. After stirring at room temperature for 1 hour, 11.4 g of triethylamine was added dropwise, and 20 ml of water was further added, and the pH of the reaction system was adjusted to 6.0 to 6.5 with triethylamine. This reaction solution was poured into cold water 5 with stirring, and after separating the precipitated brown precipitate, it was dried under reduced pressure at room temperature. The yield was 74g. The obtained 1,2-naphthoquinone-2-diazido-4-sulfonic acid ester compound was dissolved again in 300 ml of methyl ethyl ketone, and a solution of 26.5 g of 1,2-naphthoquinone-2-diazido-5-sulfonyl chloride in 300 ml of methyl ethyl ketone was added thereto. Added. After stirring at room temperature for 1 hour, 10 g of triethylamine was added dropwise. After further adding 20 ml of water, the pH of the reaction system was adjusted to 6.0 to 6.5 with triethylamine. This reaction solution was poured into cold water 5 with stirring, and the yellow brown precipitate that had precipitated was collected. After purification by reprecipitation, 84 g was obtained as a result of drying at room temperature under reduced pressure. As a result of UV spectrum analysis, 1,2-naphthoquinone-
The contents of 2-diazide-4-sulfonyl group and 1,2-naphthoquinone-2-diazide-5-sulfonyl group are 27 mol% and 16 mol%, respectively, per resin unit skeleton.
It was in mol%. Synthesis Example 3 108 g of metacresol was dissolved in 300 ml of dioxane, then 81 g of 37% formalin, and 36 g of catalyst.
% hydrochloric acid was added. Then, while stirring,
The mixture was heated to reflux for an hour. After cooling the reaction mixture,
The mixture was poured into 2.5 g of cold water with stirring, and the precipitated light brown meta-cresol-formaldehyde resin was separated and dried to obtain 112 g. The molecular weight of this resin was measured by VPO and was found to be 1540. Dissolve 60g of the above resin in 300ml of dioxane,
54 g of 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride prepared separately in dioxane
Added to 400ml solution. After stirring at room temperature for 1 hour,
After dropping 20.3 g of triethylamine and adding 20 ml of water, adjust the pH of the reaction system with triethylamine.
Adjusted to 6.0-6.5. This reaction solution was poured into 5.5 liters of cold water with stirring, and after separating the precipitated brown precipitate, it was dried under reduced pressure at room temperature. The yield was 95g. After drying, the obtained 1,2-naphthoquinone-2-
The diazide-4-sulfonic acid ester compound was dissolved again in 400 ml of dioxane, and a solution of 54 g of 1,2-naphthoquinone-2-diazide-5-sulfonyl chloride in 300 ml of dioxane was added thereto. After stirring at room temperature for 1 hour, 20.3 g of triethylamine
was dripped. After further adding 20 ml of water, the pH of the reaction system was adjusted to 6.0 to 6.5 with triethylamine. The reaction solution was poured into 5.5 liters of cold water with stirring, and a yellowish brown precipitate was collected. After purification by reprecipitation, 118 g was obtained as a result of drying at room temperature under reduced pressure. As a result of UV spectrum analysis, it was found that the 1,2-naphthoquinone-2-diazide-4-sulfonyl group and the 1,2-naphthoquinone-2
The content of -diazide-5-sulfonyl groups was 24 mol%, respectively, per resin unit skeleton. Synthesis Example 4 166g of 4-t-butylcatechol was added to dioxane.
Next, 81 g of 37% formalin and 0.5 ml of 36% hydrochloric acid were added as a catalyst. after that,
The mixture was heated to reflux for 5 hours while stirring. After the reaction mixture was allowed to cool, it was poured into 2.5 g of cold water with stirring, and the precipitated pale brown 4-t-butylcatechol-formaldehyde resin was separated and dried to obtain 162 g. The molecular weight of this resin was measured using VPO and was found to be 1,720. Dissolve 89g of the above resin in 400ml of dioxane,
54 g of 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride prepared separately in dioxane
Added to 400ml solution. After stirring at room temperature for 1 hour, 20.3 g of triethylamine was added dropwise, 20 ml of water was added, and the pH of the reaction system was adjusted with trimethylamine.
was adjusted to 6.0-6.5. Add this reaction solution to 6.5 liters of cold water.
The precipitated brown precipitate was separated and dried under reduced pressure at room temperature. The yield was 114g. After drying, the obtained 1,2-naphthoquinone-2-
The diazide-4-sulfonic acid ester compound was dissolved again in 400 ml of dioxane, and a solution of 54 g of 1,2-naphthoquinone-2-diazide-5-sulfonyl chloride in 300 ml of dioxane was added thereto. After stirring for 1 hour at room temperature, 20.3 g of triethylamine
was dripped. After further adding 20 ml of water, the pH of the reaction system was adjusted to 6.0 to 6.5 with triethylamine. This reaction solution was poured into 5.5 liters of cold water with stirring,
The precipitated yellowish brown precipitate was collected. After purification by reprecipitation and drying at room temperature under reduced pressure, 135g
was gotten. As a result of UV spectrum analysis, the content of 1,2-naphthoquinone-2-diazide-4-sulfonyl groups and 1,2-naphthoquinone-2-diazide-5-sulfonyl groups in this resin was as follows:
21 mol% and 20 mol%, respectively, per resin unit skeleton
It was hot. Example 1 A 2S aluminum plate with a thickness of 0.24 mm was degreased by immersing it in a 10% aqueous solution of tertiary sodium phosphate kept at 80°C for 3 minutes, grained with a nylon brush, and then etched with sodium aluminate for about 10 grains. Then, desmut treatment was performed with a 3% aqueous solution of sodium hydrogen sulfate. This aluminum plate was anodized in 20% sulfuric acid at a current density of 2 A/dm ² for 2 minutes to produce an aluminum plate ( ). Apply the following photosensitive liquid [A] to this aluminum plate ().
was coated and dried at 100° C. for 2 minutes to prepare a photosensitive lithographic printing plate [A] of the present invention. Photosensitive liquid [A] Compound obtained in Synthesis Example 1 0.76g Phthalic anhydride 0.2g Phenol formaldehyde resin 1.9g 2-(p-butoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine 0.02g 1 , 2-naphthoquinone-2-diazide-4-sulfonyl chloride 0.02 g Oil-soluble dye (C142595) 0.03 g Ethylene dichloride 15 g Methyl cellosolve 8 g The coating weight after drying was 2.5 g/m ² . Next, as a comparative example, in the photosensitive liquid [A], instead of the compound obtained in Synthesis Example 1, the polyhydroxyphenyl resin used in Synthesis Example 1 and 1,2-naphthoquinone-2-diazide-5-sulfonyl Photosensitive solutions [B] and [C] containing 0.88 g and 0.76 g of the condensation product () with chloride (content: 44 mol% per resin unit skeleton) were applied in the same manner as photosensitive solution [A], and exposed. I made lithographic printing plates [B] and [C]. The coating weight after drying was 2.5 g/m ² in each case. As another comparative example, the polyhydroxyphenyl resin used in Synthesis Example 1 and 1,2-naphthoquinone-2-diazide-4-sulfonyl were used instead of the compound obtained in Synthesis Example 1 in the photosensitive liquid [A]. 0.88g and 0.76g of condensation products () with chloride (content: 44 mol% per resin unit skeleton)
The photosensitive solutions [D] and [E] used were coated in the same manner as the photosensitive solution [A] to prepare photosensitive planographic printing plates [D] and [E]. The coating weight after drying is
It was 2.5g/ ^m2 . Furthermore, the condensation products () and () are mixed in a weight ratio of 1:1, and this mixture
A photosensitive solution [F] using 0.76 g was applied in the same manner as the photosensitive solution [A] to prepare a photosensitive lithographic printing plate [F].
The coating weight after drying was 2.5 g/m ² . The fluorescent light safety, sensitivity, development latitude, stability over time, and printout properties of these photosensitive lithographic printing plates were measured. Fluorescent lamp fogging was measured using a commercially available fluorescent lamp (Neolumi Super, manufactured by Mitsubishi Electric Corporation).
When a photosensitive lithographic printing plate is irradiated from a distance of 150 cm with 2 x 40W beams and then printed with a gray scale with a density difference of 0.15, it is expressed as the irradiation time required for the gray scale to change one step compared to no irradiation. Ta. Sensitivity was determined by irradiating with a Fujifilm PS light (Toshiba metal halide lamp MU2000-2-OL type 3kW).
It is expressed as the time it takes for 5 levels to become completely white on a gray scale with a density difference of 0.15. For the development latitude, developer DP-3 (manufactured by Fuji Photo Film) was diluted 7:6 and processed at 25℃ for 30 seconds and 5 minutes, resulting in a density difference of 0.15.
Gray scale solid (number of processing steps for 5 minutes - 30
It is expressed by the number of processing stages per second. Stability over time is determined by using a photosensitive lithographic printing plate at a temperature of 45°C.
It was exposed to an atmosphere with a humidity of 75% for 3 days, and was expressed as a solid gray scale with a density difference of 0.15 (number of stages treated at 45°C, 75% - number of stages not treated). The printout property was expressed as the density difference (ΔD) between the photosensitive planographic printing plates with and without printing. All development is done using developer.
The test was carried out by diluting DP-3 at a ratio of 1:6. The results are shown in Table 1.

[Table] Sample A according to the present invention has improved fluorescent lamp fogging property with almost no deterioration in sensitivity, development latitude, stability over time, and printout property. Example 2 A photosensitive lithographic printing plate G was prepared in the same manner as in Example 1 except that the compound obtained in Synthesis Example 2 was used in place of the compound obtained in Synthesis Example 1 of photosensitive liquid [A] in Example 1. It was created. Application weight after drying is 2.5
g/ ^m2 . The fluorescence fogging property, sensitivity, and development latitude of this photosensitive lithographic printing plate were measured according to the method of Example 1. The results are shown in Table 2.

[Table] Compared to Comparative Examples B to F, Sample G according to the present invention has a longer fluorescent lamp safe time without almost any decrease in sensitivity, development latitude, stability over time, and printout properties.

Claims (1)

[Claims] 1. 1,2-naphthoquinone-2-diazide-5-sulfonyl halide and 1,2-naphthoquinone-2-diazide-4 in a polyhydroxyphenyl compound
- A photosensitive composition comprising a product obtained by condensing both sulfonyl halides. 2 1,2-naphthoquinone-2-diazide-5-sulfonyl halide () and 1,2-naphthoquinone-2-diazide-4-sulfonyl halide () reacted with polyhydroxyphenyl compound
Claim 1, characterized in that the molar ratio of ()/() is in the range of 8/2 to 2/8.
The photosensitive composition described in . 3. The photosensitive composition according to claim 1, wherein the polyhydroxyphenyl compound is a condensation polymerization product of pyrogallol and acetone.