DE2064380A1 - Photosensitive copying paste - Google Patents

Description

K 2009 PP-Dr.N.-ur December 28, 1970

description
to register the

KALLE AKTIENGESELLSCHAFT
Wiesbaden-Biebrich

for a patent

Photosensitive copying paste

The invention relates to a photosensitive copying paste which works positively, i. H. their solubility by exposure increases.

Positive-working copying compounds and copying materials based on o-quinonediazides are used in reproduction technology used on a large scale. During photodecomposition, these compounds become a pincer ring carboxylic acid converted, which is more soluble in aqueous alkalis than the undecomposed compound. One can the-

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like copying layers also add higher molecular weight compounds, in particular condensation resins, in order to improve their copying and printing properties, but is not
known that these additives are included in the light reaction. The compounds have the disadvantage that they are not very photosensitive and that they are thermally labile.

Other known positive working systems exist in the
mainly from hexaaryldiimidazolylene and condensation resins. However, such copier materials result in poor performance printing plates.

The object of the invention was to find a new positive-working photosensitive copying paste with high photosensitivity and good storage stability, which could be
Develop copies with high mechanical strength

The invention relates to a photosensitive copying paste which, as essential components, contains a high molecular weight substance and a photosensitive nitrogen compound
contains and which is characterized in that the high molecular weight substance is a polymer and that the
photosensitive nitrogen compound at least one

BAD ORfG / NAL

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contains six-membered N-heterocyclic nucleus and at least one benzene nucleus as a substituent or in fused form and optionally further non-light-sensitive on these cores Contains substituents.

Preferred heterocyclic nuclei are pyridine, pyrazine or dihydropyrazine rings. Base body the heterocyclic nitrogen compounds used according to the invention are preferably acridine, Phenazine and 2,3-diphenyl-quinoxaline. The heterocyclic Base bodies preferably carry substituents or fused benzene rings. Examples of suitable Substituents are alkyl, alkoxy, nitro, dimethylamino, acetylamino, phenoxy groups and halogen atoms.

Preferred substituents are alkoxy, especially methoxy groups. In detail, for. B. the following Connections are used with success:

9-phenyl-acridine

9-p-methoxyphenyl acridine

9-p-hydroxyphenyl acridine

9-acetylamino-acridine
Benz (a) acridine
lo-methyl-benz (a) acridine

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Benz (a) phenazine

9,10-dimethyl-benz (a) phenazine

9-methyl-benz (a) phenazine / 10-methyl-benz (a) phenazine 9-methoxy-benz (a) phenazine / 10-methoxy-benz-a) phenazine dibenz Ca ₅ C) phenazine

II-methoxydibenz (a _s c) phenazine

Dibenz (a, j) phenazine

Dibenz (f, h) pyrido (2 _} 3-b) quinoxaline 6 j 4 ', 4 "-trimethoxy-2,3-diphenyl-quinoxaline 6-methoxy-2,3-diphenyl-quinoxaline 4- (4-methoxy- phenyl) -2-phenyl-quinazoline 6-chloro-H ', 4 "-dimethoxy-2,3-diphenyl-quinoxaline 6, 7-dimethyl-4', 4" -dimethoxy-2,3-diphenyl-quinoxaline 2, 3-di-pyridyl- (2) ~ 5 ~ aza-quinoxaline 2 _J 3-bis- (4-methoxyphenyl) -5 _i 6-dihydropyrazine 2,5-bis- (2,4-dimethoxyphenyl) - pyrazine 2,3j 5,6-tetrakis- (4-methoxy-pheny1) -pyrazine 2,3-dipheny1-5,6-dihydropyrazine

A large part of these compounds is already in the patent applications »P 20 27 467 and P 20 39 861 as photoinitiators for photopolymerizable copying compounds

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been beaten. The effect described there consists in polymerizing certain monomers under the action of light to stimulate, the exposed parts of the layer being hardened. In contrast, the invention Copy compounds more soluble in the exposed areas. About the mechanism of this taking place Reaction is not yet known.

Those used according to the invention are particularly preferred heterocyclic compounds the acridines substituted in the 9-position, in particular 9-phenylacridine, the 4 ', 4 "-dimethoxy-2,3-diphenyl-quinoxaline and its derivatives substituted in the 6-position, in particular the 6-methoxy derivative.

It is also possible to use light-sensitive compounds with particular advantage which are obtained by linking the aforementioned heterocyclic compounds with reactive side chains of a polymer are obtained.

The copying paste according to the invention can be used commercially in the form of a solution or dispersion, e.g. B. as so-called Copy varnish, are recovered, which the consumer himself on an individual carrier, z. B. for molding etching,

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-S-

For the production of copied circuits, stencils, signage, screen printing forms and the like. Applied and exposed after drying and developed to form the image-wise distributed layer.

The copying compound can in particular also be in the form of a solid, photopolymerizable layer located on a support as light-sensitive copying material for the production of printing forms, relief images, Etching reserves, stencils, mats, screen printing forms, color proofing foils, individual copies and the like. Bred on the market will. An important application is the production of storable presensitized printing plates for flat, letterpress and gravure printing.

The copying compounds according to the invention are distinguished by high photosensitivity and excellent thermal stability. They have diazo compounds opposite Another advantage is that no gaseous nitrogen is developed in the copy layer during exposure. they allow also the production of positive relief images or letterpress forms. The high molecular weight polymers with light

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sensitive heterocyclic side chains have no tendency to crystallize and can therefore affect the copying layers are added in relatively large proportions.

The copying compounds also contain a high molecular weight polymer, which preferably has units with acidic Substituents, in particular with carboxylic acid, phosphonic acid, sulfonic acid or N-arylsulfonyl urethane groups in combination with other units. Copolymers with acrylic and methacrylic acid esters are suitable.

The polymers form the main part of the copy paste (based on solids). The photosensitive substance is generally used in an amount of 0.5 to 30, preferably from 5 to 15 parts by weight per 100 parts by weight of polymer are added.

Dyes, pigments, plasticizers, wetting agents and color formers can also be added to the copying compositions. The- "arige Additives should preferably be chosen so that they do not absorb any light necessary for the light reaction.

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If triphenymethane or phenazine dyes are added to the layers to, these dyes are bleached out in the places struck by the light, 'so that one has an immediate visible image.

Suitable plasticizers or wetting agents are, for. B. triethylene glycol, Dibutyl phthalate, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene ethyl ether, p-nonylphenol polyglycol ether and poly waxes. With these additives, the flexibility of the layer and the speed of development can be adjusted rules.

If the copying compounds are to be applied to copper substrates, organic materials can be used to improve the adhesion Sulfur compounds, e.g. B. 2-Mereapto-benzothiazole, added will.

The copying compositions find preferred application in the production of letterpress printing plates, relief images, offset printing forms _s bimetal and Trimetalldruckformen, printed circuits, screen printing stencils and printing forms for grid-free offset printing.

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If the copying compound is stored in liquid form as a so-called copying lacquer and only immediately before the Application to the pad, e.g. B. a screen printing carrier, a circuit board or the like., Is to be applied, the layer components are dissolved or in a suitable solvent or solvent mixture dispersed. Alcohols, ketones, esters, ethers, amides, hydrocarbons and the like are suitable as solvents. Above all, the partial ethers of polyhydric alcohols, especially glycols, are used.

The solutions or dispersions can be used directly for the production of printing plates, etc. with advantage after their preparation applied to a suitable support and the products obtained as photosensitive Copying materials are stored and placed on the market. Here can be the same or solvents similar to those used for the preparation of the copier varnishes. The application is made z. B. by pouring, spraying, dipping, etc.

As a support are z. B. zinc, copper, aluminum, steel, polyester or acetate film, Perlon gauze, etc., the surface of which can be pretreated if necessary.

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If necessary, an adhesion-promoting intermediate coat is placed between the support and the photosensitive layer or an antihalation layer applied.

The copier layers exposed in the usual way are expediently made with organic solvents developed e.g. B. acetone, methyl ethyl ketone, ethylene glycol monoethyl ether, Trichlorethylene or glycerine, which you can use water or acids, e.g. B. sulfuric acid can add.

If the developed copy material is to serve as a printing form, the layer can be raised by heating higher temperature, e.g. B. above 180 ° C, "burned in" to increase the abrasion resistance and thus the number of copies.

The following examples describe embodiments of the invention. Unless otherwise stated, all percentages and quantitative ratios are to be understood as amounts by weight. One part by weight (by weight) corresponds to 1 g if 1 ecm is selected as the volume part (by weight).

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example 1

A coating solution is made

2.5 Gt. a methyl methacrylate / methacrylic acid copolymer with an average molecular weight of about 32,000 and an acid number of 137,

0.01 Gt. Supranol blue GL (CI.50.335), 20.0 Gt. Ethylene glycol monoethyl ether

and increasing amounts of 9-phenyl-acridine prepared and electrolytically roughened and through Anodizing hardened 0.3 mm thick aluminum applied by spin coating and dried at 100 ° G for 2 minutes.

The samples are then placed under a Kodak gray wedge, the wedge steps of which differ by the exposure factor 1.4, for 2 minutes with a tube exposure device from Moll, Solingen-Wald, which has 13 Philips TL fluorescent tubes ^{on an area of 60 × 60 cm 2} -Ak-40 W / 05 contains arranged, exposed.

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Developed for 30 seconds with ethylene glycol monoethyl ether, which is about 10 % water and 10 % conc. Contains sulfuric acid, and then colored with protective paint.

The results are as follows:

The light sensitivity increases with the initiator content at. The following table I gives the number of fully exposed, i.e. H. completely removed wedge steps and in brackets after that the number of intermediate stages with different 9-phenyl-acridine content.

Table I.

G t. 9-phenyl-acridine wedge steps

0.15 0 (1)

0.20 1 - 2 (1 - 2)

0.30 4-5 (1 - '2)

0.45 '5 (2)

. 0.60 6 (4)

0.75 9-10 (4)

2 0 9 8 3 0/0 8 A 5

Example 2

A care solution is made

2.5 Gt. that described in Example 1

Polymer,

0.2 Gt. 9-phenyl-acridine,
0.01 Gt. Supranol blue GL and 20.0 Gt. Ethylene glycol monoethyl ether

prepares and on electrolytically roughened and anodized hardened aluminum, its oxide layer 3 g / m 2, applied by spin coating and dried for 2 minutes at 100 ° C. The dry shift weight is 5 g / ni.

Then, as described in Example 1, under a photographic positive original exposed for removal the non-image areas for 15 seconds with acetone Developed by immersion and with aqueous sodium metasilicate solution wiped over. Then it is rinsed off with water, fixed with 1 # phosphoric acid, Colored with protective paint and, if necessary, gummed with an aqueous gum arabic solution for preservation.

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The offset printing form obtained in this way produces at least 100,000 perfect ones on a Dualith printing machine Prints.

To improve the abrasion resistance, the offset

O
The printing plate can be baked in at 240 C for 10 minutes.

The print run then increases to at least 200,000.

Example 3

A coating solution is prepared according to the example and added to sensitization with 0.2 pbw. one photosensitive nitrogen-containing compound added as indicated below.

The exposure takes place according to example 1, the processing according to example 2.

The light sensitivities observed are given in Table II below:

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Table II

Photosensitive connection

Wedge steps

6-chloro-V, 4 "-dimethoxy-2 _s 3- 6 (2)

diphenyl quinoxaline

9-phenyl-acridine 5 (2)

Benz (a) acridine 5 (2)

Benz (a) phenazine 2 (2)

6 _a 4 ^t , 4 "-trimethoxy-2,3 * -diphenyl-, 2 (2)

quinoxaline
6-acetylamino- ¹ , 4 "-dimethoxy- O (3)

2,3-diphenyl-quinoxaline

Mixture of esters from naphthoquinone- O (O) (1,2) -diazide- (2) -5-sulfonic acid and 2,3, ^ - trihydroxy-benzophenone

The known positive-working diazo compound used for comparison also yields in the specified amount significantly longer exposure time no picture.

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Example H

A coating solution is made

Oj55 Gt. that described in Example 5 Polymer,

0.70 Gt. the photosensitive compound specified below,

0.005 Gt. that used in Example 1

Phenazine dye and 15 ₃ O by weight. Ethylene glycol monoethyl ether

prepared and applied as in Example 1 to anodized aluminum and dried. The copy layer is exposed for 2 minutes under a Kodak gray wedge and 15 seconds with that in Example 1 specified developer. Then it is fixed with 1 # phosphoric acid and with fat paint colored.

The photosensitive compound used is made by reacting a copolymer of methyl methacrylate and glycidyl acrylate with 6-carboxy-4 ^f , 4 ⁿ -dimethoxy-2,3-

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diphenyl-quinoxaline prepared by the process given in US Pat. No. 3,418,295. The nitrogen content of the reaction product is 2.8 %.

Example 5

A coating solution is made

2.5 Gt. of a methyl acrylate / methacrylic acid

Copolymer with a medium Molecular weight of about 30,000 and acid number 157,

0.2 Gt. 9-phenyl-acridine,

0.01 Gt. Supranol blue GL and 20.0 Gt. Ethylene glycol monoethyl ether

prepared and centrifuged onto anocUsed aluminum and dried. In a parallel experiment, the copy layer is coated with a 1 - 2 / U thick layer provided with polyvinyl alcohol and processed similarly. Exposure and development are done accordingly Example 1.

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- αδ -

If the photosensitivities of the two samples are compared, this is 180% higher in the case of the latter, in which the post-diffusion of oxygen is inhibited by the overcoat during exposure.

This effect is also observed when using nitrogen-containing heterocycles other than light-sensitive ones Connections observed.

Example 6

A coating solution is made

2.5 Gt. a copolymer of methyl

methacrylate and N- (p-toluenesulfonyl) -carbamic acid-Cß-methacryloxyJ-ethyl ester (65:35, acid number 60), 0.2J Gt. 9-phenyl-acridine,

0.004 Gt. Ethyl violet (CI. Basic Violet k) and 20.0 Gt. Ethylene glycol monoethyl ether

prepared and on 0.3 mm thick, anodized aluminum flung up.

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2Ü643? 0

l-I after drying is under a positive original or under a KODAK gray wedge 4 minutes on one 5 KVJ xenon point light lamp COP XP 5000 from the company Staub, Neu-Isenburg, exposed and 10 seconds developed by treatment with the developer given in Example 1. The quality of the received Image corresponds to that of the images described in Example 3.

Example 7

A coating solution is prepared according to the example but without dye and spun onto a 125 / U thick, biaxially stretched polyester film, which is provided with a hydrophilic adhesion promoter layer according to DAS 1 228 4i4, and dried.
Exposure and development correspond to Example 1.

This copy can be made in an A. B. Dick offset duplicator Model 321 clamped and used to make prints.

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2Q6438Q

Example 8

A coating solution is made

2.5 Gt. Methyl methacrylate / acrylic acid mixed

polymer with a medium

Molecular weight of 60,000 and

the acid number 82,

0.25 Gt. Polyoxyethylene sorbitan monolaurate. (TWEEN ^ 20 of the Atlas Chem. Ind.,

Inc., Wilmington),
0.4 Gt. 9-phenyl-acridine,
0.01 Gt. of a phenazine dye accordingly

Example 1 and
20.0 Gt. Ethylene glycol monoethyl ether

prepared and spun onto anodized aluminum and dried. It is exposed for 2 minutes under a positive original or under a KODAK gray wedge according to the example 1, developed for 30 seconds by immersion in trichlorethylene. Then it is fixed with 1 # phosphoric acid and colored with Pett color. The printing plate is now ready for printing.

2ub'438O

Example 9

A coating solution is made

2.5 'Gt. of the polymer described in Example 1,

0.2 Gt. 9-phenyl-acridine, 0.75 pbw. Polyoxyethylene sorbitan mono laurate

(TWEEN ^ 21) and 5.0 Gt. Ethylene glycol monoethyl ether

prepared and poured onto a 0.3 mm thick aluminum sheet. Most of the solvent is allowed to evaporate at room temperature and dried then after 3 hours at 100 ° C.

To produce a relief image or a letterpress form, the copying layer is treated with the for 20 minutes Röhrenbelxchtungsgerät exposed and exposed according to Example 1 under a photographic positive original then developed for 5 minutes with the developer specified in Example 1 by brushing over.

The thickness of the copy layer is 0.43 mm, the washout depth 0.185 mm.

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" ²² " 2Ub4380

Instead of the polyethylene sorbitan monolaurate , polyoxyethylene acetyl ether, p-nonylph'eriol polyglycol ether or triethylene glycol can also be used.

The resulting relief images are comparable in quality.

Example 10

A coating solution is made according to Example 2 prepared and with 0.1 Gt. 2-mercapto-benzothiazole added. Then it is spun onto a cleaned copper surface of a Cu / Al bimetal plate, then dried at 100 ° C. for 2 minutes.

Exposure takes place for 2 minutes under a positive original or under a KODAK gray wedge according to Example 1, then developed for 40 seconds with the developer specified in Example 1.

To produce a bimetal offset printing plate, the exposed copper is etched with ferric chloride ("400 Series" ALC Etch, Type LS 402, the Fred K.H. Levey Co., Inc., New York / USA) etched away within a minute, then wiped over with 1 # phosphoric acid and then colored with fat paint.

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-23- 206438U

Example 11

For production of. Parb test films are four coating solutions prepared according to Example 2, but instead of the dye used there as follows stained:

a) Yellow foil: 0.07 pbw. Fat yellow 3 G (CI.12.700),

b) red foil: 0.08 Gt. Zaponechtfeuerrot B '

(CI. Solvent Red 109),

c) Blue foil: 0.01 pbw. Ethyl violet

(CI. Basic Violet 4),

d) Black foil: 0.08 Gt. Fat black HB (CI. 26.150).

These solutions are each 37 / U thick, biaxial stretched polyethylene terephthalate film spin-coated and dried as in Example 2. Then the layers are under the associated silver film separations (3 minutes blue or red foil, 5 minutes yellow or black foil) exposed with a tube exposure device and developed with the developer specified in Example 1 for 15 seconds in each case.

When the extracts are placed on top of each other, a dem is created Original of the silver film excerpts corresponding duplicate.

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Example 12

A coating solution is made

2.5 Gt. that described in Example 1

Polymer, 0.2 pbw. Benz (a) acridine, 0.01 pbw. Zaponechtfeuerrot B (CI. Solvent

Red 109) and 20.0 Gt. Ethylene glycol monoethyl ether

prepares and on an aluminum / copper / chrome trimetal plate centrifuged and dried.

Then, as in Example 1, exposure is carried out using a negative original and the one specified there Developer Developed for 30 seconds.

The exposed chromium is etched with a solution of 17.4% CaCl ₂ 35.3% ZnCl _2, 2.1% HCl and k 5.2% water in 7 minutes and then the resist layer was removed with alcohol. Finally, 1% phosphoric acid is wiped over and colored with Pett paint. The tri-metal plate is ready for printing.

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" ²⁵ " 21) 84380

Example 13

To produce a zinc high-pressure form, a coating; * solution is made

2j5 Gt. that described in Example 1

Polymer,
0.2 over 4 ', 4 "-Dimethoxy-2,3-diphenyl-

quinoxaline,

0.02 Gt. Ethyl violet (CI. Basic Violet 4) and 20.0 Gt;, ethylene glycol monoethy lather

prepared and applied to a cleaned one-step zinc etched plate by spin coating and dried.

Exposure is carried out for 3 minutes using a tube exposure device corresponding to Example 1, developed for 1 minute with the developer specified in Example 1.

Then the exposed zinc surface is etched with 6 nitric acid at room temperature for 6 minutes. The shape created in this way is suitable for quality letterpress printing.

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example Ik

A coating solution is made

2.5 Gt. that described in Example 1

Polymer,

0.2 Gt. 4 ^! -tert-butyl-9-phenyl-acridine, 0.02 pbw that used in Example 12

Dye and 20.0 pbw. Ethylene glycol monoethyl ether

prepared and spin-coated onto a mechanically roughened, 0.3 mm thick aluminum foil applied and dried.

Exposure and development are carried out as in Example 1. The quality of the printing plate obtained corresponds that of those described in Example 2.

Example 15

A coating solution is made

2.5 Gt. of the polymer described in Example 1,

0.2 Gt. 6-chloro-i} ', 4 "-dimethoxy-2,3-diphenylquinoxaline,

Q, 25 Gt. of the wetting agent used in Example 8,

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0.02 Gt. Ethyl violet (CI. Basic Violet 4) and 15.0 Gt. Ethylene glycol monoethyl ether

manufactured and on a monofilament perlon fabric that 120 threads per cm, applied and dried.

It is exposed for 5 minutes under a negative original using a tube exposure device according to Example 1 and then for 2 minutes with that given in Example 1. Developer developed.

The stencil obtained in this way can be used for screen printing.

Example 16

A coating solution according to Example 15 is applied to the cleaned copper surface of a carrier, which consists of a plastic plate with a laminated copper skin, applied and dried. Dry layer weight: 10 g / m.

Then, under a positive original, exposure is carried out for 10 minutes with a tube exposure device according to Example 1,

BATH ORIGINAL 209830/0845

Developed for 30 seconds with the developer specified in Example 1 and then with an iron (III) chloride solution etched from 42 ° Be for 20 minutes.

The copying layer used is characterized by excellent etching resistance and good resolution the end.

Example 17

A coating solution is made

2.5 Gt. a methyl methacrylate / methacrylic acid copolymer with an average molecular weight of about 20,000 and an acid number of 95,

0.01 Gt. Rhodamine B ,.

0.2 Gt. 2,3-bis (ii'-methoxyphenyl) -5,6-dihydro-

pyrazine,
20.0 Gt. Ethylene glycol monoethyl ether

prepared, applied to electrochemically pretreated 0.1 mm thick aluminum by spinning at 100 revolutions per minute and dried at 100 ° C for 2 minutes.

2 09 8 30/0 8 4.5.

Ό.λπγ. viird the plate under a positive original in the Burning from 72 cm with an 8000 W xenon lamp for 2 minutes beliohtot. The development takes place by wiping over nil the developer specified in Example 1 within of 35 seconds.

After fixing with 1 # phosphoric acid, with colored in bold color.

The quality of the printing plate obtained is similar to that described in Example 3.

Example 18

A coating solution is made

2.5 pbw of the polymer described in Example 17,

0,: 15 Gt. 2 ₃ 5-bis- (2 ', 4'-dimethoxyphenyl) -pyrazine, O, Cl Gt. Rhodamine B,

0.2 Gt. of the wetting agent used in Example 8 and ,: 'u, 0 Gt. Cyclohexanone

electrochemically pretreated boron'ltet and istarkes to 0/1 mm.! • ■ IL-Ώ aluminum applied by Aufschleuder'n at 100 revolutions j -i i'Unute. After drying, the plate is

BATH ORIGINAL

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exposed under a positive original for 2 minutes' from a distance of 72 cm by an 8000 V / xenon lamp.

This exposed plate is developed in 45 seconds by wiping with the developer specified in Example 1 and after treatment with 1% phosphoric acid with Colored protective color.

The quality of the printing plate obtained corresponds to that of those described under Example IJ.

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Claims (9)

Photosensitive copying paste, which is an essential component of a high molecular weight substance and contains a photosensitive nitrogen compound, characterized in that the high molecular substance is a polymer and that the photosensitive nitrogen compound contains at least one six-membered N-heterocyclic nucleus and at least one Benzene nucleus as substituents or in fused form and optionally no further ones on these nuclei Contains photosensitive substituents. 2. copying paste according to claim 1, characterized in that the heterocyclic core is a Is pyridine, pyrazine or dihydropyrazine ring. 3. copying paste according to claim 1, characterized in that the photosensitive nitrogen compound is of high molecular weight and contains a large number of light-sensitive residues. 2098 30/08 4. copying compound according to claim 2, characterized characterized in that the photosensitive nitrogen compound is an acridine, a 2 ', 3-diphenylquinoxaline substituted by methoxy groups or a phenazine. 5. copying paste according to claim 1, characterized in that it is a solid photosensitive
Layer is present on a carrier. 6. copying compound according to claim 5, characterized in that it is on the exposed layer side carries a cover film that is not very permeable to oxygen. 7 · copying paste according to claim I ₃ thereby characterized in that they are a polymer with acidic
Contains substituents. 8th; Copy paste according to claim 7, characterized characterized in that they are a polymer with carboxylic acid, Phosphonic acids sulfonic acid or N-arylsulfonyl urethane groups contains. 209830/0845 33 - 9. copy paste according to claim characterized in that it contains O _S 5 to 30 parts by weight of photosensitive compound per 100 parts by weight of polymer. , - ^ _n if ' ORIGINAL INSPECTED 2098 30/0845