AU633192B2

AU633192B2 - Colored positive-working photosensitive recording material and a process for the production of a color test image using this material

Info

Publication number: AU633192B2
Application number: AU72656/91A
Authority: AU
Inventors: Martin Benzing; Andreas Elsaesser; Ine Gramm; Shane Hsieh; Guenther Hultzsch; Juergen Mertes; Manfred Michel; Dieter Mohr; David Siegfried
Original assignee: Hoechst AG
Current assignee: Hoechst AG
Priority date: 1990-03-05
Filing date: 1991-03-05
Publication date: 1993-01-21
Anticipated expiration: 2011-03-05
Also published as: AU7265691A; DE59108856D1; DE4006856A1; CA2037492A1; JPH04218052A; EP0447829B1; EP0447829A3; EP0447829A2

Description

i Our Ref: 356017 FORM10

AUSTRALIA

Patents Act COMPLETE SPECIFICATION

(ORIGINAL)

Application Number: Lodged: Complete Specification Lodged: Accepted: Published: Priority: Related Art: Applicant(s): Hoechst Aktiengesellschaft 6120 Frankfurt/Main

GERMANY

ARTHUR S. CAVE CO.

Patent Trade Mark Attorneys Level 10, 10 Barrack Street SYDNEY NSW 2000 Address for Service: 0 Complete specification for the invention entitled "Colored positive-working photosensitive recording material and a process for the production of a color test image using this material".

The following statemeit is a full description of this invention, including the best method of performing it known to me:- 1046U:AB

MENOMW

COLORED POSITIVE-WORKING PHOTOSENSITIVE RECORDING MATERIAL AND A PROCESS FOR THE PRODUCTION OF A COLOR TEST IMAGE USING THIS MATERIAL Background of the Invention 5 The present invention relates to a positiveworking colored photosensitive recording material for the production of a color test image, composed re(eaSeI (alyer suppor4 of a 4 t ::rary lay .arri:-, a photosensitive layer containing dyestuff or pigment, binder and quinonediazide conmpound and an adhesive layer which can be activated by means of heat, and to a process for the production of a color test image using this material.

Color testing is in general performed ii, 15 multicolor printing to allow correction of the color separations used for exposure printing plates.

The color test image must be a true record of the required dot or line image and should reproduce the tone value of the col--s in a form true to nature, i.e. in neithu an increased nor reduced form.

Visual color testing should indicate defects in the -la- 1 1, K^

-OP"L^

i master, allow the best color reproduction to be expected by machine printing, reproduce the accurate gradation of all color shades and indicate whether the gray shades are neutral. It sould furthermore indicate any need to attenuate one of the colors and/or give an indication to change the film master befoie production of the printing plates.

Color testing for multicolor printing has to date been carried out with the aid of color proofs.

All the steps which are also needed for the actual multicolor printing must be taken in this process.

Such a color test process is expensive and timeconsuming, and other color test processes have therefore been developed, which are intended to be 15 of equivalent quality to the proof. Three color test e *processes using photosensitive color test films are known, the surprint process (laminating on top of one another), the surlay process (copying on top of one another) and the overlay process (laying on top of one another).

DE-A 2,712,864, corresponding to GB-A 1,550,524, describes a positive-working color film which consists of a transparent layer carrier, a layer containing a photosensitive diazonium salt and a thin color layer containing a dispersed pigment.

A specific layer arrangement is characteristic of this color test film, and the layer containing the photosensitive diazonium compound should in all cases be above the color layer with respect to the 3n exposure stage.

EP-A 0,035,028, corresponding to US 4,260,673, relates, to a presensitized color test -2sheet which has the following layer build-up: a carrier sheet is covered with anon-stick coating, onto which a color layer is applied, followed by a novolak-containing binder layer which contains a reaction product of a resin and a diazo oxide and is free from pigments. This binder layer is then also followed by a barrier layer and a non-stick layer.

EP-A 0,217,792 relates to a process for improving the exposure range of positive-working color test films in which a colored release layer is used as an optical filter. A color test film which, in addition to the other layer build-up, also additionally contains one or more dyestuffs which effect protection from reflection ("antihalation S 15 layer") is known from EP-A 0,165,030.

EP-A 0,165,031, corresponding to US 4,656,114, discloses a color test sheet in which, between the color layer and the adhesive layer, there is an additional water-insoluble transparent barrier layer which is intended to prevent diffusion from one color layer into another color layer after the adhesive layer has been dissolved.

The primary aim of these known color test processes is to produce a multicolor image which is as close as possible in appearance to the four-color print sought. The decisive disadvantage of these positive-working recording materials for the production of color test films seems to be that these materials use novolak resins in combination with quinonediazide processes as the photoreactive system. Since novolaks have a yellow to brown -3r coloration, this unavoidably leads to a shift in color shade in the color test image to be produced.

All the color test systems known to date which are based on precolored layers containing novolak are therefore to be regarded as a compromise between photoreactivity and color reproduction.

In EP-A 0,179,274, corresponding to US 4,659,642, an attempt is made to avoid the color shift due to the intrinsic coloration of the novolak by using binders which are free from phenol groups.

However, this does not yet lead to materials which are suitable in practice, since the differentiation between the solubility of the exposed and nonexposed regions is inadequate.

15 Various processes based on precolored layers

S..

are known for the production of color test films for

S..

-the graphics industry. US 3,671,236 describes a process in which separation images in the various base colors are combined in succession on a receiver sheet in accordance with the corresponding color separations to give a four-color overall image.

US 3,721,557, corresponding to DE-B 1,912,864, describes a process for transferring color images, in which a peel-off layer is applied S 25 between the photosensitive layer and the layer carrier. When the photosensitive layer is developed, the soluble constituents of the layer are removed selectively and a visible image forms. The layer carrier with the image is pressed against a suitable receiver material coated with adhesive and the image is then transferred by peeling off the layer -4i I I carrier. A fresh adhesive layer is applied to the receiver material for each further image transfer.

A color test process in which positiveworking photosensitive layers, colored in the desired base colors and in each case on a temporary carrier film, are exposed and developed on this film is known from DE-A 2,236,941, corresponding to US 4,093,464. The resulting separation images are transferred onto an image-receiving material, for example a printing paper, by lamination in register.

This process has the disadvantage that lamination in register requires very precise work and is therefore very expensive. Furthermore, lamination of developed images can be carried out only with layers 15 which are still sufficiently thermoplastic, i.e. as a rule only with positive-working iayers which e *S additionally also contain certain plasticizing additives.

According to EP-A 0,035,028, a multicolor test image is produced by laminating the multilayered material onto an image-receiving material, which is a paper with a water-proof Sfinish, and exposing it on this material and developing it into the separation image. The other 25 separation images are produced over the first in the same manner. Multicolor images in accurate register can be obtained more easily by this process, since it is merely necessary to perform the exposure in register. The process has the disadvantage that several layers on top of one another are required for each base color and that the image elements I "r II still each contain two layers containing nondecomposed colored diazo compound.

Summary of the Invention Accordingly, it is an object of the present invention to provide a photosensitive recording material for a multicolor proof which allows reproduction true to the color location and results in an adequate developer contrast between the exposed and non-exposed regions.

Another object of the present invention is to provide an improved process for the production of a color test image, using the improved colored photosensitive recording material.

In accomplishing the foregoing objectives, 15 there has been provided, in accordance with one aspect of the present invention, a positive-working colored photosensitive recording material for the production of a color test image comprising: a re. (ecatbe- (cye-r- $L or' 4 to mporaryl -yr o 4:rir; a release layer. omprising polyvinyl alcohol on the surface of A 4th temporary rleasab sPForf layr arr a photosensitive layer comprising (i) a dyestuff or pigment, (ii) a binder comprising a novolak-free phenolic polymer resin, a reaction product of said phenolic polymer resin with a monoisocyanate or a mixture thereof, and (iii) an esterification product of a compound containing at S. least one phenolic hydroxyl group and oquinonediazide sulfonyl chloride; and an adhesive layer which is activatable by means of heat and which comprises an alkali-insoluble organic polymer and an alkali-soluble polyester.

In accordance with another aspect of the present invention there is provided a process for producing a color test image comprising the steps ;uPPo rof: providing a permanent layer, =wEr; (b) S:fiport

A

laminating to the layer, rrir a recording material as described above via the adhesive layer of the recording material, wherein the photosensitive layer of the recording material comprises at least one dyestuff or pigment of a base color selected from the group consisting of cyn, magenta, yellow and re. -e f le yer- supPort black; peeling off theAte*petary libycr arrie-- S.of the recording material; exposing the 15 recording material under a color separation corresponding to the color; developing the recording material u_ produce a separation image; laminating to the separation image another recording material as dez-ribed above via its; adhesive layer, wherein the photosensitive layer of the recording material comprises at least one dyestuff or pigment of a different base color; and producing additional separation images for each remaining base color and black by sequentially 25 repeating steps whereby a complete fourcolor image is formed.

Other objects, features and advantages of the present invention will become apparent to those skilled in the art from the following detailed description. It should be understood, however, that the detailed description and specific examples, while indicating preferred embodiments of the -7present invention, are given by way of illustration and not limitation. Many changes and modifications within the scope of the present invention may be made without departing from the spirit thereof, and the invention includes all such modifications.

Detailed Description of the Preferred Embodiments According to the invention, a positiveworking colored photosensitive recording material of the type mentioned, at the beginning comprises a co Mpi(Atq release layer, b cd on polyvinyl alcohol p esent on the surface of the riora 1 photosensitive layer containing, as the quinonediazide compound, an esterification product of a compound containing one or more phenolic 15 hydroxyl groups and o-quinonediazide-sulfonyl chloride, and, as binder, a novolak-free phenolic polymer resin and/or a reaction product of the polymer resin with a monoisocyanate, and an adhesive layer containing or composed of a styrene-butadiene copolymer and an alkali-soluble polyester.

Partly hydrolyzed polyvinyl acetates, in particular those having a degree of hydrolysis of about 80 to 90 mol percent, are suitable for the release layer based on polyvinyl alcohol.

25 The novolak-free phenolic polymer resin is preferably a polymer having phenolic groups in the side chain, comprising units corresponding to the general formula I -8- 0 I i I

-(CH

2

CR

1 A I B (OH)p in which

R

1 is hydrogen or a methyl group,

O

II

A is a single bond or the group -C 0 B is an optionally substituted mono- or polynuclear carbocyclic aromatic ring system, p is 1 or 2.

A binder which is a polymer corresponding to the general formula I, in which

S

*r S U

S.

R

1 is hydrogen or a methyl group, 25 A is a single bond or the group -C O and B is phenylene or naphthylene, which can be substituted by lower alkyl, lower alkoxy, aryl or halogen, is employed in particular.

The novolak-free phenolic polymer resin is preferably a binder which further comprises units according to formula II

(CHR

2 CR3R 4

(II)

in which R2

R

3

R

4 is hydrogen or a carboxyl group, is hydrogen, alkyl or a halogen atom, is alkyl, alkoxy, alkoxycarbonyl, acyl, acyloxy, aryl, formyl, cyano, carboxyl or hydroxyl, and if R2 is a carboxyl group, can be bonded thereto to form an acid anhydride.

9 1 I A binder which is a polymer corresponding to the formula II, in which R2 is hydrogen or a carboxyl group, R3 is hydrogen, (C 1

-C

12 )-alkyl, or a halogen atom, R4 is alkyl, alkoxy or alkoxy carbonyl having in each case 1 to 4 carbon atoms, acyl, acyloxy, aryl, formyl, cyano, carboxyl or hydroxyl, and if A, is carboxyl group, can be bonded to this to form an acid anhydride, is employed, i partic ula The novolak-free phenolic polymer resin is preferably a binder comprising units of formula I from about 60 to 100 mol percent and units of formula II from about 0 to 40 mol percent.

Particularly suitable polymer resins as binders are homopolymers of pyrocatechol monomethacrylate, rasorcinCol mf,.nmothay:ylate, resorcinol monomethacrylate, hydroquinone monomethacrylate and 4-hydroxystyrene or copolymers thereof. These res.is can be present by themselves or as a mixture.

The polymer resin employed as the binder can be prepared by conventional methods, for example in the presence of a polymerization initiator, such as azo-bis-isobutyronitrile, in organic solvents such as tetrahydrofuran or methyl ethyl ketone, at elevated temperatures in the course of 1 to 20 hours. However, suspension or bulk polymerization, which can be triggered off by radiation, heat or ionic initiators, .i also possible. The polymers containing units of the formula I can be homopolymers or copolymers corresponding to the formula I and II. i.e. including one or more vinyl r O monomers, if appropriate also those containing phenolic groups.

Examples of these are styrene, achlorostryrene, a-methylstyrene, 3- or 4chloromethylstyrene, 4-bromostyrene, methyl vinyl ether, ethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, acrylonitrile, acrolein, butadiene, acrylic acid, methacrylic acid, the methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl, 2-ethylhexyl, phenyl, benzyl, biphenyl or naphthyl esters of these acids, methacrylamide, acrylamide, vinyl acetate, vinyl isobutyl ketone and maleic anhydride. Comonomers containing phenolic hydroxvl groups preferably have the following structure: HC Ch 1 i

S

O =C C O SCH, -i

OH

The molecular weight of the polymer can be varied within wide limits. Polymers where M about 20,000-50,000 are preferred here.

The hydroxyl number is in general in the range from about 100 to 450, preferably between *D -11i t about 200 and 350. The proportion of units containing phenolic hydroxyl groups in the polymer depends on the photosensitivity in practice of the various colored photosensitive layers. The proportion is furthermore determined by rapid development with aqueous-alkaline solutions and by the highest possible resistance of the non-exposed regions to developer. The desired hydrophilicity is established by reaction of the OH groups with, for example, monoisocyanates. Examples of suitable isocyanates are butyl isocyanate, cyclohexyl isocyanate and n-propyl isocyanate. The monoisocyanate used for the reaction product with i. the phenolic polymer resin is preferably phenyl 15 isocyapate.

r r e r 4eIy W ,e-amount of monoisocyanate is in the range S. from about 0 to about 30 percent by weight, based on the polymer present.

The binder is present in the ,olored pre- Mrbly ore 20 photosensitive layer in an amount of about 20 to preferably about 30 to 70, percent by weight, based on the non-volatile contents of the layer.

To prepare the mixtures according to the invention for the photosensitive layer, the binder described is combined with a color-donating component and a photosensitive compound. These include, above all, o-quinonediazides. o- Quinonediazides which can be present are condensation products of a compound having one or 30 more phenolic hydroxyl groups and 1,2naphthoquinone-2-diazide-4-sulfonic acid chloride, 1,2-naphthoquinone-2-diazide-5-sulfonic acid -12- .4

S

4,

S

44 S chloride or 1,2-naphthoquinone--2-diazide-6-sulfonic acid chloride. The compounds containing one or more phenolic hydroxyl groups include, for example, trihydroxybenzophenone, bisphenol A or 4-tert.butylphenol. The o-quinonediazides which are preferably used are esterification products of 1,2naphthoquinone-2-diazide-4-sulfonic acid chloride with 2,3,4-trihydroxybenzophenone, which cause no color shift in the color test film after exposure.

The mono-, bis- and triesters are possible esterification products of 2,3,4-trihydroxybenzophenone and 1,2-naphthoquinone 2-diazide-4sulfonic acid chloride. The trisester,is specially eS T r T CLTI Of) preferably employed. The amount of o-quin nz1iaiidopnd.A is in general about 10-30%, based on the non-volatile constituents of the photosensitive mixture.

The coloring agents which are suitable according to the invention include various classes of dyestuffs and pigments in the base colors of magenta, cyan, yellow and black. Mixtures of the various dyestuffs or pigments can also be used to achieve certain color shades. In the most preferred embodiment, pigments having an average particle size of not more than about 1 pm are employed.

The individual components are dissolved in compatible solvents, such as, for example, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, 7-butyrolactone and methylglycol and the solution is applied to the surface of the tempo ary layer carrier and dried. The photosensitive 1 yer has a layer weight of about 0.5 to 5.0 g/m 2 The -13- -14layer weight is, most preferably, between about 0.8 and 2.0 g/m 2 The releasable layer support preferably has at least one non-stick surface, i.e.

it should be capable of holding the photosensitive layer so that it can be released from it again. For this purpose, either the layer support surface can be non-stick in nature, it can be rendered non-stick by a suitable treatment, or it can be provided with a release layer. A layer based on polyvinyl alcohol is used according to the invention as such a release layer. Suitable polymers include, for example, polyvinyl alcohol and partial esters thereof, polyvinyl ethers and acetates, and copolymers of vinyl alcoiol and olefins, which can be employed by themselves or as a mixture. A partly hydrolyzed polyvinyl acetate having a degree of hydrolysis of about 80 to _'0 mol percent is preferably used as the polymer for the release layer. The release layer has a dry layer weight preferably in the range from about 0.5 to 2 g/m 2 The adhesive layer which can be activated by means of heat is preferably composed of an alkali-insoluble organic polymer and an alkali-soluble polyester resin, the softening point of -,ich here preferably less than about 160 C, more preferably less nan 100 oC. The adhesive layer moreover should not be tacky at room temperature. These substances include, for example, polyvinyl acetate, polyacrylic acid esters, acrylic acid ester copolymers, polymethacrylic acid esters, methyacrylic acid ester copolymers, polyvinyl chloride, vinyl chloride copo'ymers, polystyrene, styrene copolymers, polyester resins and ethylene copolymers (for 2 example ethylene/vinyl acetate copolymers or ethylene/acrylic acid copolymers).

The adhesive layer contains about 60 99, preferably about 70 95 percent by weight of styrene-butadiene copolymer and about 1 40, preferably about 5 percent by weight of alkali-soluble polyester.

If appropriate, the materials described above can also contain other components, such as, for example UV absorbers, antistatics and plasticizers.

921020,p:\oper\jmw,72656.spC, 4

I

15 The adhesive layer is usually applied to the photosensitive layer from an organic solvent. Mixing of the two layers is avoided here by using a solvent which does not attack the lower photosensitive layer. The dry weight of the adhesive layer preferably is in the range from about 2 to 20 g/m 2 more preferably from about 3 to 10 g/m 2 The layers which have been exposed image-wise can be developed with aqueous-alkaline solutions in a known manner. The aqueous developer solutions can contain, for example, alkali metal phosphates, silicates or hydroxides and furthermore wetting agents, as well as small amounts of organic solvents.

In a process for the production of a color test image using a colored photosensitive recording material according to the invention, a recording material in the first base color is laminated u, the adhesive layer side thereof onto a permanent layer support with the aid of pressure and heat, the releasable layer support is peeled off, the recording f e 921020,p:\oper\jmw,72656.spec,15

I

material is exposed under the color separation onto the corresponding base color and developed, and separation images of the other base colors and of black are further produced over the resultir separation image in a corresponding manner, the complete four-color image being formed.

To produce a color test image, the laminate is laminated via the adhesive layer onto a permanent pPort layer iA e under pressure and by heating, the photosensitive layer 4is exposed image-wise, after re(Tesc EOyer 64 thet mporar lay. oarrizr has been removed, and the exposed layer is developed by washing out the exposed regions. To produce a complete color test image, another photosensitive recording material in 15 a different base color is laminated onto the image *produced beforehand on the same permanent layer S carrier. In order to obtain the entire color reproduction, four layers are usually used, in the colors cyan, magenta, yellow and black.

20 The photosensitive layer according to the vention is particularly suitable for the production of color test images on a suitable 4 permanent layer carrier material, since it avoids a ror shift in the color of the color test image due to 25 novolaks by using colorless polymer resins which, as a result of their content of phenolic groups, have a solution-inhibiting effect, like novolaks, on quinonediazide compounds and are significantly superior to resins containing no phenolic groups in their photoreaction.

-16r Jw ir The photosensitivity in practice can moreover be adjusted according to the invention by modifying the phenolic hydroxyl groups with monoisocyanates.

Films of plastic, for example polyester films or paper coated with plastic, can be used as permanent layer 5:r:r The surface of the permanent layer A .Arrier preferably has a rough surface and/or has been treated with, an adhesion Suppo rT promotor. The permanent layer rriz': must be insensitive towards the laminating and developing operations.

The result of the invention is that a positive-working colored photosensitive recording material which guarantees a color reproduction which 15 is true to nature, is easy to handle in a simple

S*

process, and has a broad processing tolerance and r, good developer resistance of the non-exposed regions can be provided for production of a color test image.

20 The invention is illustrated in more detail with the aid of the fo'lowing examples, without limiting it to these. Unl.ess stated otherwise, all the parts and percentage data are based on the S" weight.

25 The following example relates to the production of a color test film colored cyan.

S Example 1 A release layer which has a dry weight of 0.7 g/m 2 is applied to a polyethylene terephthalate film 30h cr as the .e 1sc: ye.. u::po The 50 gm, thick as the temporary layo carrier. The -17-

I

solution is knife-coated on and dried at 100 0 C in a drying cabinet for 3 minutes.

Coating solution A Polyvinyl alcohol 120.0 g (Molecular weight 530, degree of hydrolysis 88 mol Polyvinyl alcohol 120.0 g (Molecular weight 1000 degree of hydrolysis 88 mol%) Nonylphenol polyglycol ether 6.7 g deionized water 6.8kg SIn the subsequent step, the colored photosensitive layer is applied to the release layer with the aid of a whirler. The coating solution for S 15 the photosensitive layer is prepared in two stages.

The pigment dispersion is first prepared.

Coating solution B Polyvinylpropional resin containing 13.6% of vinyl acetate groups, 9.8% of vinyl alcohol groups and 76.6% of vinylpropional groups Hosterpermblau B2G blue pigment, Color Index 74160 Propylene glycol monomethyl ether 44.0% y-Butryolactone 44.0% -18- I

K

S.

S

Coating solution C Polymer of pyrocatechol monomethacrylate 12.5 g (Reduced specific viscosity value: 0.210 in dimethylformamide [DMF]) Coating solution B 6.5 g Esterification product of 1.1 g 1 mol of 2,3,4-trihydroxybenzophenone and 3 mol of 1,2-naphthoquinone 2-diazide- 4-sulfonic acid chloride Propylene glycol monomethyl ether 36.4 g Tetrahydrofuran 43.5 g The solution is whirler-coated onto the film, which has been provided with a release layer, such that a layer weight of 1.5 g/m 2 is established after 15 drying (2 minutes, 110 0 The color density, measured through a blue filter using a Gretag densitometer, is 1.2.

Finally, an adhesive layer composed of 97 percent by weight of a styrene-butadiene copolymer (glass transition temperature 50 0 C) and 3 percent by weight of an alkali-soluble polyester (DesmophenR 1700, BAYER AG) is also applied, with a dry weight of 3 g/m 2 onto the colored photosensitive layer.

The color test film thus obtained is laminated with the adhesive layer onto a receiver sheet as the permanent layer carrier. Suitable laminating temperatures are in the range from 110 to 140 0 C. After the lamination, the film as the temporary layer carrier is peeled off. The adhesive layer and the colored photosensitive layer remain on the permanent layer carrier during this operation.

S. *S S

S

55* -19-

C

C.

C

The photosensitive layer is then exposed image-wise in a known manner. It can be exposed, for example, through a photomask in a vacuum copying frame using a UV light source.

After the exposure, the layer is developed with an aqueous-alkaline solution composed of Water 92 parts by weight Sodium octylsulfate 3 Potassium metasilicate 3 Phenoxyethanol 1 Trisodium phosphate 1 the soluble portions of the layer which have been affected by the light being removed.

A true reproduction of the original color 15 separation is obtained.

To produce a complete color image, in the same manner and in successive operations, a magenta, a yellow and a black cQoored film are each laminated on, the particular t -mporary la r barnrr is peeled off and the layer is exposed and developed, so that accurate reproduction of the original from which the color separations have been prepared is effected.

Examples 2-7 For comparison, the polymer from Example 1 is modified with the amounts of phenyl isocyanate stated in the table and a color test film is produced and in each case developed with the same developer solution analogously to Example 1. The polymers used and the open wedge steps in the UGRA wedge for the same exposure times, as well as the resolutions f or the individual layers are summarized in Table 1 6 0 0 r II" 0 Table 1 Example by weight Open step g-line still of phenyl visible isocyanate 2 0.9 5 3 1.8 4 4 3.6 3 5.5 2 6 7.3 2 7 9.1 L 8 The table shows that the hydrophilicity of the imaging layer can easily be varied by the amount of pheny isocyanate.

Examples 8-11 To produce a color test film, the following binders are mixed in accordance with the data for coating solution C with the components stated for that solution: 8) Copolymer of pyrocatechol monomethacrylate and methyl acrylate (90:10 mol%, reduced specific viscosity value: 0.438 dl/g in dimethylformamide) 9) Copolymer of hydroquinone monomethacrylate and nbutyl methacrylate (70:30 mol%, reduced specific viscosity value: 0.365 dl/g in dimethylformamide) on a -22- MEMOM r Copolymer of resorcinol monomethacrylate and 2ethylhexyl methacrylate (68:32 mol%, reduced specific viscosity: 0.589 dl/g in dimethylformamide) 11) Copolymer of 4-hydroxystyrene and n-butyl methacrylate (70:30 mol%, reduced specific viscosity: 0.321 dl/g in dimethylformamide) After the lamination, exposure and development, a true reproduction of the original color separation is obtained.

.0 The copolymers employed in the open wedge steps in the UGRA wedge for the same exposure times, as well as the resolutions for the individual layers, are summarized in Table 2.

Table 2 Example Open step l-line standing 8 4 9 2 8 2 8 11 6

C.

0 Ce C0~0 *e

CC..

*r

CC

0 -23-

Claims

1. A positive-working colored photosensitive recording material for the production of a color test image comprising: a releasable layer support, adjacent to, a release layer comprising polyvinyl alcohol on the surface of said releasable layer support adjacent to, a photosensitive layer comprising a dyestuff or pigment, (ii) a binder comprising a novolak-free phenolic polymer resin, a reaction product of said phenolic polymer resin with a monoisocyanate or a mixture thereof, and (iii) an esterification product of a compound containing at least one phenolic hydroxyl group and o-quinonediazide sulfonyl chloride, adjacent to an adhesive layer activatable by means of heat which comprises an alkali-insoluble organic polymer and an alkali-soluble polyester.

2. A recording material as claimed in claim 1, wherein said release layer comprises a partly hydrolyzed polyvinyl acetate. a c r I I r c 0' 01 92102,p:\oper\jmw,72656.spec424 -i I I II I r-rr~T~

3. A recording material as claimed in claim 2, wherein said partly hydrolyzed polyvinyl acetate has a degree of hydrolysis of about 80 to 90 mol percent.

4. A recording inaterial as claimed in claim 2, wherein said release layer consists essentially of a partly hydrolyzed polyvinyl acetate.

5. A recording material as claimed in claim 1, wherein said binder comprises a polymer resin comprising units according to the formula I: -(CH 2 CR 1 I B (OH) S..in which S 20 R1 is hydrogen or a methyl group, II A is a single bond or the group -C 0 B is an optionally substituted mono- or polynuclear carbocyclic aromatic ring system, p is 1 or 2. 30

6. A recording material as claimed in claim wherein said binder comprises a polymer resin according to the formula I in which R 1 is hydrogen or a methyl group, O A is a single bond or the group -C 0 and B is phenylene or naphthylene, which can be substituted by lower alkyl, lower alkoxy, aryl or halogen. 25 I r i

7. A recording material as claimed in claim 1, wherein said binder further compriseS units according to the formula II: (CHR 2 CR 3 R 4 (II) in which R2 is hydrogen or a carboxyl group, R 3 is hydrogen, alkyl or a halogen atom, R 4 is alkyl, alkoxy, alkoxycarbonyl, acyl, acyloxy, aryl, formyl, cyano, carboxyl or hydroxyl and if R 2 is a carboxyl group, can be bonded thereto to form an acid anhydride.

8. A recording material as claimed in claim 7, wherein said binder comprises units .cording to 15 the formula II *r *L S. S 55 S (CHR 2 (2R 3 R 4 (II) in which R2 is hydrogen or a carboxyl group, R 3 is hydrogen, (C C12)alkyl, or a h;ogen atom, R4 is alkyl, alkoxy, alkoxycarbonyl, acyl, acyloxy, aryl, formyl, cyano, carboxyl or hydroxyl, and if R2 is a carboxyl group, can be bonded thereto to form an acid anhydride.

9. A recording material as claimed in claim wherein said binder comprises a polymer resin comprising units of formula I from about 60 to 100 mol percent.

10. A recording material as claimed in claim 7, wherein said binder comprises a polymer resin comprising units of formula II from about 0 to 40 mol percent.

11. A recording material as claimed in claim wherein said binder is selected from the group 26 I. consisiting of homopolymers of pyrocatechol monomethacrylate, resorcinol monomethacrylate, hydroquinone methacrylate and 4-hyuroxy-styrene, copolymers thereof and lixtures thereof.

12. A recording material as claimed in claim 1, wherein said binder _s a reaction product of a novolak-free phenolic polymer resin with a monoisocyanate.

13. A recording material as claimed in claim 12, wherein said monoisocyanate is phenyl isocyanate.

14. A recording material as claimed in claim 15 12, wherein said monoisocyanate is present in an i* amount fromA to about 30 percent by weight, based on .the polymer present.

15. A recording material as claimed in claim 20 1, wherein said binder is present in an amount from about 20 to 75 percent by weight, based on the non- volatile contents of the photosensitive layer.

16. A recording material as claimed in claim 25 15, wherein said binder is present in an amount from about 30 to 70 percent by weight, based on the non- volatile contents of the photosensitive layer.

17. A recording material as claimed in claim 30 1, wherein said esterification product is an esterification product of 1,2-naphthoquinone 2- diazide-4- or 5-sulfonic acid chloride with 2,3,4- trihydroxybenzophenone, bisphenol A or 4-tert.-butyl- phenol. 27 I I r 28

18. A recording material as claimed in claim 17, wherein said esterification product is an esterification product of 1,2-naphthoquinone 2-diazide-4-sulfonic acid chloride with 2,3,4-trihydroxybenzophenone.

19. A recording material as claimed in claim 1, wherein said esterification product is present in an amount of about 10 to 30 percent by weight, based on the non-volatile constituents of the photosensitive mixture.

A recording material as claimed in claim 1, wherein the color of said dye or pigment is a base color selected from the group consisting of cyan, magenta, yellow and black.

21. A recording material as claimed in claim 1, wherein said adhesive layer comprises a styrene-butadiene copolymer *nd an alkali-soluble polyester.

22. A recording material as claimed in claim 21, wherein said adhesive layer comprises about 60 99 percent by weight of styrene-butadiene copolymer and about 1 to 40 percent by weight of said alkali-soluble polyester. S: 20

23. A recording material as claimed in claim 22, wherein said adhesive layer comprises about 60 95 percent by weight of styrene-butadiene copolymer and S" about 5 30 percent by weight of said alkali-soluble polymer.

24. A process for producing a color test image comprising the steps of 25 providing a permanent layer support; laminating to said layer support a recording material as claimed in claim 1 via the adhesive layer of said recording material, wherein the photosensitive layer of said recording material comprises at least one dyestuff or pigment of a base color selected from the group consisting of cyan, magenta, yellow and black; peeling off the releasable layer support of said recording material; 921028,p:\oper\imw,72656.spec,28 II -29 exposing said recording material under a color separation corresponding to said base color; developing said recording material to produce a separation image; lamin,.i, a to said separation image a recording material as claimed in claim 1 via th nesive layer of said recording material, wherein the photosensitive layer of .o recording material comprises at least one dyestuff or pigment of a different base color; and producing additional separation images for each remaining base color and black by sequentially repeating steps whereby a complete four-color image is formed. A positive-working colored photosensitive recording material for the production of a color test image substantially as described herein with reference to any one of the examples. 20 DATED this 28th day of October, 1992 Hoechst Aktiengesellschaft S' By Its Patent Attorneys DAVIES COLLISON CAVE o 921025,p:\oper\jmw,72656.spec,29