DE2420372A1 - LIGHT SENSITIVE MATERIAL AND METHOD OF MANUFACTURING THEREOF - Google Patents

Description

Dipl.-Ing. H. MITSCHERLICH 8 MONKS 22

Dipl.-Ing. K. GU NSCHMANN Steinsdorfstrasse ΙΟ

Dr.rer. nat. W. KÖRBER Dipl.-Ing. J. SCHMIDT-EVERS

PATE N TA N WALT E

April 26, 197 ² *

VICKERS LIMITED
Vickers House
Millbank Tower, Millbank London SW 1 / England

Patent application

Photosensitive material and process for its manufacture

The invention relates to photosensitive material and in particular such a photosensitive material which is suitable for making printing plates.

The invention provides a light-sensitive material is provided which is formed by a product, which 'can be obtained in that a polymer which _s includes a plurality of epoxy groups, hydroxyl groups or primary and / or secondary amino groups with the Halosulfonylgruppe at least one compound of the

- '2 -

general formula

. , COOH X _: - R - (CR _{1 β} CR ₂ ) _a - CR =

is reacted, wherein R represents an aromatic radical which can optionally be substituted with one or more groups in addition to the X group, a is either 0 or 1, R ^ _3, R2 and R ₃ , which can be the same or different, each represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an aralkyl group or an alkoxy group, R ₁ ^ represents a hydrogen atom when a is 1 or when a = 0 or 1, an alkyl or alkoxycarbony! group or, more preferably, a group selected from the carboxyl, cyano, deactivated phenyl and halosulfonylphenyl groups, and X represents a halosulfonyl group, or in the case in which R ₁ ^ is a halosulfonylphenyl group. group and only then a deactivation group.

When R _{1 is} a halosulfonylphenyl group, a deactivating group, for example a halogen substituent, must be present on the aromatic radical R in order to prevent a halosulfonyl group from entering R, which would lead to crosslinking between R and R ₄ . Similarly, when X is a halosulfonyl group and R ₁ ^ is a pheny group, R ₁ ^ must contain a deactivating group.

It is _{particularly preferable for R 4} in the formula that it contains a carboxyl group, since this results in the alkali

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solubility of the photosensitive material is improved. It is also particularly preferable that a in of the formula has a value of one instead of zero because the resulting increased unsaturation increases photosensitivity of the material increased.

In the case where the polymer has a variety of Contains hydroxyl groups, it can be, for example, a. Epoxy or phenoxy resin (derived from a bisphenol and epichlorohydrin); Poly (vinyl alcohol); a partially hydrolyzed poly (vinyl ester) such as PοIy (vinyl alcohol acetate); a naturally occurring material such as cellulose or starch and derivatives thereof that are partially produced by a Esterification or etherification, e.g. hydroxypropyl cellulose, have been formed; Poly (hydroxyethyl acrylate) or Poly (hydroxyethyl methacrylate); partially hydrolyzed Acetals such as partially hydrolyzed poly (vinyl butyral), partially hydrolyzed poly (vinyl cinnamal), and mixtures of this; a condensation product of phenol or a substituted phenol with an aldehyde e.g. phenol-formaldehyde resin, Resorcinol formaldehyde resin and 2,4-dihydroxybenzoic acid formaldehyde resin; or a condensation product of a substituted or unsubstituted one Phenoxyalkanol with an aldehyde, e.g. the resin formed by the condensation of 2-phenoxyethanol with formaldehyde. The condensation products of phenols and phenoxyalkanols with aldehydes differ in the following Molecular construction

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where η is at least 2; R _{5 represents} from 0 to 3 substituents selected from the alkyl, halogen, alkoxy, hydroxy, aryl and aralkyl groups; R _{g represents} a hydroxy or hydroxyalkoxy group; and R _{7 represents} a hydrogen or a lower alkyl, aryl or aralkyl group.

In the case where the polymer contains a multiplicity of primary and / or secondary amino groups, can it is, for example, poly (ethyleneimine); Poly (vinylamine); an aniline-formaldehyde resin; or the product that received is made by condensing a styrene maleic anhydride copolymer or an alkyl vinyl ether maleic anhydride copolymer with an excess of an aliphatic or aromatic diamine, which product through the following repeating unit is labeled:

CH CH GH - OEt -.

ι - ι ^? -

C = O COOH

₀
ο

where Rg represents an aliphatic or aromatic group and R is an alkoxy or phenoxy group.

In the case where the polymer contains epoxy groups, it may be an epoxy resin made by Condensation of epichlorohydrin and, for example, bisphenol A or a novolak epoxy resin produced by Condensing a phenol (or cresol) formaldehyde novolak resin and epichlorohydrin.

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Suitable compounds that have a halosulphonyl group included are:

ti)

/1.1 / ^ r

C U c

Chlorosulfonylcinnamylidene malonic acid

coo \\

Chlorosulfonyl- <& -chlorocinnamyliderimalonic acid

c \ - \ = ' CA- CU-CL

Chlorosulfonylcinnamylidenecenetic acid

r j

CH = C

COOH

et - (Chlorosulfonylphenyl) -chlorζ imtic acid

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μ cooH

Chlorine sulfonyl- <λ - (chlorophenyl) cinnamic acid

Such compounds can be used individually, in combination with one another or in combination with one or more Halides or other aromatic sulfonic acids and of aliphatic and aromatic carboxylic acids are used which halides have no free carboxylic acid groups contain. For example, the compound or compounds containing the specified halosulfonyl group contain, can be used in combination with the halides, for example chlorides of p-toluenesulphonic acid, Acetic acid, propionic acid, benzoic acid, p-azidbenzoic acid or cinnamic acid. The reaction of such acidic Halides that do not contain free carboxylic acid groups with the polymer can not only simultaneously with the Reaction of the specified halosulfonyl group-containing compound of the above general formula take place, but also before or after.

The photosensitive material of the present invention is soluble in alkali and has a polymeric "backbone" with which light-sensitive side chains with terminal carboxylic acid groups by sulfonyloxy groups or sulfonamide groups are connected. In the case where the group X is a halosulfonyl group and the polymer is a plurality of Contains hydroxyl groups, the photosensitive material becomes

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formed by groups of the following formula:

COOH

-0-SO ₂ -R- (CR ₁ =

bonded to carbon atoms of the polymer, where R, R ^, R ₂ , R ₃ and a have the meanings given above and R ₁ ^ an alkyl group, an alkoxycarbonyl group, a carboxyl group, a cyano group, a phenyl group substituted with a terminal activating group or a hydrogen atom is.

In the case where the group X is a halosulfonyl group and the polymer contains a large number of primary and / or secondary amino groups. Appropriate photosensitive material groups of the following formula:

COOH i

- N - SO ₀ - · R - W- "vi ~ ^ ¹ - ¹¹ O J _n " ^s - ^ilx y

eL ! c .. Θ. J "V ^

bonded to carbon atoms of the polymer, where R, R., R ₀ , R- and a have the meanings given above, and R ₁ , an alkyl group, an alkoxycarbonyl group, a carboxyl group, a cyano group, a phenyl group substituted with a deactivating group or a hydrogen atom is.

In the case where the group R ^ is a halosulfonyl substituted one Is phenyl group and the polymer contains a large number of hydroxyl groups, the photosensitive

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borrowed material groups from the following formula:

HOOC

= OR ₃ - (CB ₂ *

bonded to carbon atoms of the polymer, where R, R ^ ₉ R ₂ $ R ₃ and a have the meanings given above, j Ph is a phenyl group and X is a deactivating group.

In the case where the group R ^ is a Halosulf onylphenylgruppe and the polymer containing a plurality of primary and / or secondary amino groups _s comprises erfindungsgeiTilße photosensitive material groups of the following formula?

HOOC _V

β _s CR2- (CH ₂ «CR ₁ ) _a -RX

bonded to carbon atoms of polymer ₉ where R ₉ R _{1 9} R ₂ 9 R ₃ and a have the meanings given above j Ph is a phenyl group and X is a deactivating group ·

Although the photosensitive material _{9 of} the present invention which contains the aforementioned groups bonded to carbon atoms is usually produced by reacting the halosulfonyl compound with epoxy-5, hydroxy or amine groups of a polymer ₉ , the material can be produced by others

Procedures can be prepared as illustrated in Example 9.

The "photosensitive materials of the present invention are of particular value in the manufacture of photographically made printing plates and the like .. The invention therefore further comprises a photosensitive plate having a support made of a material on which a The film of the photosensitive material adheres, for example glass, paper, resin-impregnated paper, Resin film, or metal, such as aluminum, zinc, magnesium or copper, which is a layer of the carrier photosensitive material.

To apply the photosensitive layer to the The support is the photosensitive material in a suitable solvent or in a mixture of solvents, such as dimethylformamide, dioxane, 2-ethoxyethanol, 2-ethoxyethyl acetate or ethyl methyl ketone, dissolved and the resulting solution is applied to the support in a conventional manner, for example by Immersion, spraying or by a fluidized bed process. Then the solvent either through Dry in air or evaporated by heating, leaving a layer of the photosensitive material on remains with the wearer. The coating weight per square meter is generally between 0.2 and 2.0 g.

In industry it can be desirable for coating purposes be, the photosensitive material according to the invention dyes, pigments, plasticizers, wetting agents, To add sensitizers, stabilizers, non-reactive polymers and the like.

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In use, the photosensitive plate is exposed image by image for a period of time that depends on the composition the layer, the layer thickness, the carrier, the brightness of the light source and the intended one Product depends. The areas not exposed to light remain soluble in alkali, while the surfaces exposed to light become insoluble. The picture on the exposed plate is therefore developable by an alkali.

The alkaline aqueous solution used for developing the exposed plate is said to have a good solvent action on the areas not exposed to light have little effect on the photohardened image. An alkaline developer that can be used appropriately is an aqueous solution of a phosphate or a metasilicate of an alkali metal. This solution 5 - 30% of a water-miscible organic solvent, e.g. an alcohol, can be added to to facilitate the complete removal of all unexposed material.

Preferred fields of application for the photosensitive material according to the invention are the production of lithographic materials Printing plates, the production of etch resists, the production of printed circuits u. dj-., for chemical milling, and the production of ornamental Effects.

The following examples illustrate the invention:

example 1

(a) The preparation of chlorosulfonylcinnamylidene malonic acid (formula i)

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Cinnamaldehyde and malonic acid were condensed in glacial acetic acid at 100 ⁰ C with each other, the condensate was recrystallized from ethanol and a melting point of at 2O6 ° C determined. The condensate was reacted with chlorosulfonic acid at 60 ^° C. and the chlorosulfonylcinnamylidenemalonic acid obtained was isolated by slowly pouring the reaction mixture into hot water with stirring.

(b) " The manufacture of resorcinol / formaldehyde resin

Resorcinol, excess formaldehyde and sodium sulfate were dissolved in water and placed on a water bath with stirring warmed up. After the solution became cloudy, the reaction was made cold by adding a large volume Water ends. The precipitate was filtered off, washed with water and dried at room temperature.

Cc) The manufacture of the photosensitive material

Equivalent weights of chlorosulfonyl monomylidene malonic acid and resorcinol-formaldehyde resin, prepared as described _{above 9} , were dissolved in acetone and a sodium carbonate solution was added. The mixture was ^{stirred at 20 °} C. for one hour. The photosensitive ester obtained was filtered off, dissolved again in water and then precipitated by adding hydrochloric acid »

Cd) - The manufacture of a printing plate

A 3% solution of the above photosensitive Material in a mixture of dimethylformamide and 2-ethoxyethanol was applied by means of a centrifugal apparatus the surface of a sheet of electro-grained (electrograinedj and anodized aluminum so that a

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2 coating weight of about 0.5 g / m 2 was obtained. After drying, the photosensitive plate obtained was exposed to a 4000 watt pulse xenon lamp at a distance of 0.65 m for 2 minutes in contact with a negative. The exposed plate was developed with a 2.5% strength solution of trisodium phosphate in order to remove those areas of the photosensitive coating which were not exposed to light during the exposure. The plate was then washed with water and 2% igea? Sulfuric acid washed and colored with a fat dye.

Example 2

(a) The manufacture of photosensitive material

6.3 g of "Epikote 1009" epoxy resin from Shell Chemicals (produced by the polycondensation of 2,2-bis (p_-hydroxyphenyl ) propane with excess epichlorohydrin in the presence of sodium hydroxide and with a molecular weight of about 3750) were dissolved in 33 ml of anhydrous dioxane and 11.9 g of chlorosulfonylcinnamylidene malonic acid were prepared as described above, added with stirring. The mixture was heated under reflux for 8 hours, cooled, diluted with an equal volume of dioxane and added dropwise to 1500 ml of water. The precipitated one Resin was filtered off and washed with more water on the filter.

(b) Making a printing plate

The procedure of Example Kd) was carried out using the

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above photosensitive material with the exception repeats that the developer for the exposed plate by a mixture of four parts of 12% aqueous Sodium metasilicate and 1 part of 2-ethoxyethanol was formed.

Example 3

(a) The manufacture; of photosensitive material

· + G 2-phenoxyethanol-formaldehyde resin, manufactured by the acid-catalyzed condensation of 2-phenoxyethanol and formaldehyde, and 15 g of chlorosulfonylcinnamylidene malonic acid, prepared as indicated above were in dioxane for 8 hours at reflux temperature implemented. The product was isolated by pouring the cooled reaction mixture dropwise into one liter Water was entered.

(b) Making a printing plate

The procedure according to Example Kd) was repeated with the exception that an exposure time of 5 minutes and a three part 15% aqueous trisodium phosphate developer and 1 part of 2-ethoxyethanol were used.

example

(a) The production of ol-chlorosulfonylphenyD-ctilor-zimic acid (formula iv)

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A mixture of 56.2 g 4-chlorobenzaldehyde, 54 ₉ 4 g
Phenylacetic acid, 80 ml acetic anhydride and 40 ml
Triethylamine was refluxed for 5 hours. Unreacted 4-chlorobenzene aldehyde .wurde
removed by steam distillation and the residue dissolved in aqueous alcohol and treated with bleaching carbon. Crystals of phenyl-4-chlorocinnamic acid were obtained by acidifying the solution. The product was recrystallized from alcohol and determines that it has a melting point of 202-4 ⁰ C.
The chlorosulfonyl derivative was prepared according to the procedure described in Example 1.

b) Manufacture of photosensitive material

A solution of 24 g of resorcinol-formaldehyde resin (prepared as in Example 1) in 400 ml of dimethylformamide
36 g of <& - (chlorosulfonylphenyD-chlorocinnamic acid, prepared as above, and 32 g of chlorosulfonylcinnamylidene-malonic acid as prepared in Example 1. The mixture was ^{cooled to about 50 °} C. and a saturated one was added
Solution of sodium carbonate added dropwise until the pH was between 8 and 10. After standing for 4 hours, the solid was filtered off, dissolved in water and reprecipitated by acidifying the solution with hydrochloric acid.

(c) Production of a printing plate

The procedure of Example 1 (d) was followed with the exception
repeats that the developer by a 7.5%
Trisodium phosphate solution was formed.

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Example 5

(a) Manufacture of photosensitive material

10.6 g of Wresinoid R751 (a phenol-formaldehyde resin manufactured by Resinous Chemicals Ltd.) was dissolved in 40 ml of anhydrous dioxane and added to 4.2 g of p-azide benzoyl chloride. 2.5 ml of pyridine were added and the mixture heated to 5 0 ⁰ C for 4 hours. The ester was precipitated by adding water and air dried at room temperature. The product was dissolved in 200 ml of dimethylformamide and 24 g of chlorosulfonylcinnamylidene malonic acid (prepared as in Example 1) were added with stirring. The solution was cooled to 5 ° C and a saturated sodium carbonate solution was added dropwise until the pli value was between 8 and 10. After standing for about 8 hours, the solid was filtered off, redissolved in water and the product was precipitated by acidification with hydrochloric acid.

(b) Making a printing plate

The process according to Example Kd) was repeated with the exception that the developer was replaced by a 7.5% strength trisodium phosphate solution was formed.

Example 6

Ca) Preparation of chlorosulfonylcinnamylidenecyanacetic acid (formula iii)

Cinnamaldehyde and cyanoacetic acid were condensed and convert the product into the corresponding Chlorsulfony! derivative

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converted using the procedure described in Example Ka). The melting point of the acid was 210 to 212 ° C.

(b) Manufacture of photosensitive material

To a solution of 1.09 g of resorcinol-formaldehyde resin (prepared as in Example 1) in 21 ml of dimethylformamide was added a solution of 3.5 g of the above chlorosulfonylcinnamylidenecyanoacetic acid in 20 ml of dimethylformamide. The mixture was ^{cooled to 5 °} C. and the pH value was adjusted to approximately by means of a saturated sodium carbonate solution. After standing for 8 hours, the mixture was acidified and the product filtered off.

(c) Making a printing plate

The procedure of Example Kd) was repeated with the exception that the developer was replaced by a 0.5% trisodium phosphate solution was formed.

Example 7

(a) Preparation of chlorosulfonyl- 6- chlorocinnamylidene-malonic acid (formula ii)

80 g of phosphoryl chloride was added dropwise to 80 ml of chilled dimethylformamide. M-8 g acetophenone were added 5 minutes more than H and the mixture stirred at 0 ⁰ C for another 60 minutes. The mixture was left to stand overnight at room temperature and then poured into a solution of 600 g of sodium acetate in 1500 ml of water. β-chlorocinnamaldehyde was separated off as a red oil. The mixture was

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extracted with ether and the ethereal solution dried over anhydrous sodium sulfate. Evaporation of the ether yielded 44 g of β-chloroformaldehyde. β- Chlorcinnamaldehyde and malonic acid were condensed to give β-chlorcinnamylidene-malonic acid and this was converted to the corresponding chlorosulfonyl derivative using the procedure described in Example Ka).

(b) Manufacture of photosensitive material

1.09 g resorcinol-formaldehyde resin (manufactured as in Example 1) and 3.33 g of <$ -chlorosulfonylcinnamylidene-malonic acid, prepared as before, were according to the example 6Ca) process described condensed.

(c) Making a printing plate

The procedure of Example 6 (c) was repeated.

Example 8

(a) Manufacture of photosensitive material

5.0 g of chlorosulfonylcinnamylidene malonic acid (prepared as in Example 1) and 3.3 g of the product obtained by common Condensation of Lytron 822 (a styrene-maleic anhydride copolymer, which is marketed by Monsanto) and excess ethylene diamine were reacted together in the presence of aqueous NaOH to give a pale yellow alkali-soluble resin obtain. The product was made by pouring the mixture into water, filtering off the precipitated material, and air drying isolated at room temperature.

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- - 18 -

(b) Making a printing plate

The procedure according to Example Kd) was repeated, but the developer consisted of a 12% sodium metasilicate solution.

Example 9

(a) Manufacture of photosensitive material

The light-sensitive material of Example 8 was prepared by using the styrene-maleic anhydride copolymer with the condensation product of chlorosulfonylcinnamylidene malonic acid and excess ethylenediamine was implemented. This was done by dissolving 12 g of chlorosulfonylcinnamylidene malonic acid (prepared as in Example 1) in 24 ml Dioxane and slowly adding the solution drop by drop into a vigorously stirred solution of 6 g of ethylenediamine in 24-0 ml Dioxane. The yellow solid product was dissolved in water and diluted hydrochloric acid until it was completely precipitated of Aminoäthylsulfonamideinnamyliden malonic acid hydrochloride, 2 g Lytron 822 was dissolved in anhydrous dimethylformamide to make a 20% solution and 2. t g des Hydrochloride in 10 ml of dimethylformamide was added. The mixture was shaken to give a clear solution. 1.0 ml of triethylamine was added and the mixture was stirred for an additional 30 minutes. The product was through Pour the mixture into water, filter off the precipitated material, and air dry at room temperature.

(b) Making a printing plate

The procedure of Example 8 (b) was repeated.

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Example 10

(a) Manufacture of photosensitive material

1.4t g of a polyethyleneimine with a molecular weight from 50 - 100 χ 10 (supplied by Dow Chemical Co. Ltd.) were dissolved in 30 ml of 2N sodium hydroxide and 10.5 g of chlorosulfonylcinnamylidene-malonic acid {prepared as in Example 1) added in 50 ml of cyclohexanone. The mixture was shaken and acidified for 30 minutes. That Product was filtered off and washed with water.

Cb) making a printing plate

2 g of the above product were mixed with a hot mixture stirred by dimethylformamide and dimethyl sulfoxide and that undissolved material removed by filtering. 0.1 g Neozapon Blue FLE (Badische Anilin & Soda-Fabrik), a phthalocyanine blue dye and 0.1 g of 5-nitroacenaphthene was added and stirred into the solution. The solution then became used to produce a photosensitive plate in the manner described in Example 1 and the plate was exposed and treated as described in this example.

latent in sayings ;

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Claims (17)

Patent application back Method of making a photosensitive Material, characterized in that a polymer containing a large number of epoxy groups, hydroxyl groups or primary and / or secondary amino groups are reacted with a compound which has a halosulfonyl group and has the following general formula: '■ J on -R- (CR ₁ - H ₂ where R represents an aromatic radical; a is either zero or one; R ^, R ₂ and R _3, which are identical or different and ₅ are each a hydrogen atom, a halogen atom, a cyano group, an alky! Group, an aryl group, an alkoxy group, an aryloxy group, an Aralky! Group or an aralkoxy group, R ₁ ^ an alkyl group, an alkoxycarbonyl group, a carboxyl group, a cyano group ₉ a phenyl group substituted with a deactivating group ₉ an ixalosulfonyl-substituted phenyl group, or _s when a is one _{9 represents} a hydrogen atom and X a halosulfonyl group, except when R _{4 is} a halosulfonyl-substituted phenyl group , in which case X is a deactivating group. 409845/1009 2. The method of claim 1, wherein the polymer contains a plurality of hydroxyl groups, thereby characterized that "the polymer is an epoxy resin, a phenol / aldehyde resin, a phenoxy resin, poly (vinyl alcohol), Cellulose, a cellulose derivative, a partially hydrolyzed poly (vinyl ester), poly (hydroxyethyl acrylate), Poly (hydroxyethyl methacrylate), a partially hydrolyzed Acetal, or a condensation product of a phenoxy alcohol and an aldehyde. 3. The method according to claim 2, characterized in that the phenol / aldehyde resin is a resorcinol-formaldehyde resin is. M-. The method of claim 1 wherein the polymer contains a large number of primary and / or secondary amino groups, characterized in that the polymer a poly (vinylamine), an aniline / formaldehyde resin, the condensation product of a styrene / maleic anhydride copolymer or an alkyl vinyl ether / maleic anhydride copolymer with an excess of an aliphatic or aromatic diamine or a poly (ethyleneimine). 5. The method of claim 1, wherein the polymer is a Contains a plurality of epoxy groups, characterized in that the polymer is an epoxy resin or a novolak / epoxy resin is·. 409845/1009 - 22 - 6. The method according to the preceding claims, characterized in that in the formula a is one, R ₁ ^ is a carboxyl group and X is a halosulfonyl group. 7. The method according to claim 6, characterized in that the mentioned compound chlorosulfonylcinnamylidene malonic acid is. 8. Process according to claims 1-5, characterized in that the compound mentioned is chlorosulfonyl _T delta-chloro-cinnamylidene-malonic acid, chlorosulfonylcinnamylidene-cyanoacetic acid or chlorosulfonyl-alpha (chlorophenyl) -cinnamic acid. 9. The method according to claims 1-5, characterized in that in the formula R ₁ ^ is a halosulfonylphenyl group and X is a deactivation group. 10. The method according to claim 9, characterized in that said compound is alpha (chlorosulfonylphenyD-chloro-cinnamic acid is. 11. The method according to the preceding claims, characterized in, that the polymer is also reacted with a halide, which consists of an aromatic Sulfonic acid, an aliphatic carboxylic acid or an aromatic carboxylic acid is derived and not a free one 409845/1009 Contains caronic acid group. 12. Photosensitive material, characterized in that this by the method according to the preceding Claims has been made. 13. Photosensitive material characterized by groups of the formula: y COOH = CR-) - CE, - C ^or y COOH = CR ₂ ) _a -CH ₃ = C bonded to carbon atoms of a polymer, where R is an aromatic radical; a is either zero or one; R 1, R 1 and R ₃ , which can be the same or different, each represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an aralky group or an alkoxy group; and R _{1+ is} an alkyl group, an alkoxycarbonyl group, a carboxyl group, a cyano group, a phenyl group substituted with a deactivating group or a hydrogen atom. 14 ·. Photosensitive material, characterized by groups 409845/100 ^ - 2k - from the formula: C-CR-, - (CR ₂ = CH ₁ ) _a -HX -0-SOp-Fh HOOC ^or bonded to carbon atoms of a polymer, where R is an aromatic radical; a is either zero or one; _{R 1} , R 1 and R 3, which may be the same or different, each represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an aralkyl group or an aralkoxy group; Ph is a phenyl group and X is a deactivating group. 15. Photosensitive plate, characterized by a carrier with a layer of a photosensitive Material according to claims 12, 13 or 14 coated is. 16. A method for producing a printing plate, characterized in that that imagewise a photosensitive plate according to claim 15 is exposed and a developer the plate is applied in order to avoid light exposure 409845/1009 to remove struck areas of the layer and to leave an image on the carrier, which through the is formed by areas of the layer acted upon by light. 17. Printing plate, characterized in that it has been produced by the method according to claim 16. r patent attorney A0 9845/1009