SU1062640A1 - Light-sensitive colour-photographic halogensilver material with dir-components - Google Patents

Abstract

Photosensitive colour photographic material are made with >=1 Ag halide emulsion layer contg. a DIR coupler of formula (I) or (II) in which K is a chromogenic gp. contg. a radical which prevents diffusion and has an opt. substd. acylacetanilide, 1-aryl-pyrazolone-(5)-, 1-naphthol or phenol structure, the original hydrophilic-substd. inhibitor gp. being bound in the coupling position; Z completes a heterocyclic 5- or 6C ring; X is O, S or NR2 where R2 is H or 1-5C alkyl; and R1 is -OR3, -COOR3, -SO2NHR3 or -SO3R3 where R3 is H, ammonium ion or metallic ion. (I) and (II) are easily synthesised yelow, purple or green-blue coupler, with a controlled DIR effect, and high stability in the photographic material. When used in multilayer colour photographic Ag halide materials they give images with good sharpness, grain and colour yield. They give good inter- and intra-image effects. Due to their hydrophilic character they are more easily incorporated into the photographic prod. than previous DIR couplers.

Description

This invention relates to a photosensitive color photographic halogen-silver material which, in order to improve the transmission of colors and details, contains new DIR components.  It is known that in photosensitive colors: silver halide materials can be used to improve the display quality of the color components, which, respectively, exhibit release inhibitors of manifestation during the chromogenic manifestation.  These are commonly referred to as DIR components, their structures, combination mechanisms, and photographic actions are described in detail by Barr et al.  in phot.  Sc i. Engn.  13,274-79 (1969) and in US-PS 3,148 JD DIR components.  photographic properties such as sharp contour of color grain and color rendition can be improved, which is based on diffusion of the released inhibitor of the inner layer that contains the DIR component (intralayer effect) and diffusion into neighboring layers (interlayer effect).  The intralayer effect improves the detail display, while the interlayer effect can be used to correct colors for unwanted side absorption of dyes.  These effects, based on diffusion and inhibitory action, are described by Hanson and Cardboard in j. Optical Soc. America 42633-669 (1952), Tglie BlZ. Wiss, Photogr. , Photophys, Photochem.  47, 106. 118 V and 246-255 (1952) and DE-OS 2 509 722.  In addition, the DIR components can be used according to US-PS 3 620 747 to control the gradation and the associated increase in brightness, image colors, and also according to DE-OS 2 533 176 to reduce the veil of the product.  laziness, especially with high-speed processing.  The chemical structure of the known DIR-components includes, in particular, acylacetanilide, 5-pyrazolone, phenol and 1-naphthol basic structures, which are associated with the usual anti-diffusion ballast group.  Particularly active DIR components carry heterocyclic mercaptoazoles, α-amines, acryl mercaptans, or mercaptocarboxylic acids as cleavable groups.  Moreover, the most typical double-equivalent substituents in the combination position are 2-nitro or 2-aminophenylthio, benzthiazol-2-ylthio, 1-phenyltetrazol-5-ILTIO-, 5-F9NIHL-1,3,4- oxadiazol-2-ylthio, or benzoxazol-2-ylthio group; , Methods for the preparation of numerous DIR components that contain typical inhibitory groups are described in US-PS 3 148062, 3 227 551 ,.  3,227,554 and 2,247,496.  However, the use of the DIR component as the only color-forming element is impossible, since the strong inhibitory effect of the leaving group inhibits the color development so much that even with high-temperature treatment, a low dye output is achieved.  This requires mixing with the colored components, which form the dyes of the same absorption region with the best dye yield.  Examples of mixtures from two to seven known components with DIR components for improved sharpness, grain and color reproduction are described in US-PS 3 703 375 and DE-OS 2 530 645.  However, due to the low concentration of the DIR components (less than 10%) and in most cases, a higher combination rate of the added color components often fails to achieve a complete reconciliation of the DIR components.  This results in too low concentrations of the released inhibitor of the manifestation, not enough to. provide interlayer effects by diffusion into adjacent layers.  Therefore, there are special applications of the known DIR components, for example, in the auxiliary and intermediate layers, which serve only the color of the interlayer effect.  They are described, for example, in US-Anm.  454 525, UE-PS 3 006 759, in DE-OS 2 429 250; and DE-OS 2 421 544.  They are called 11C, 1L C- and llE-components.  The use of higher concentrations of the known DIR components, furthermore, is limited by the fact that the so-called anti-tidal effect also reduces sensitivity and gradation.  It occurs if, due to insufficient resistance against hydrolysis or other reasons, there is a disproportionate release of the inhibitor before or during the color development or if it was not possible to limit the residual inhibitor content due to the synthesis method to less than 0.5 %  The latter requires a great deal of technical and economic efforts in the production of these components / which is often difficult or not at all possible.  Therefore, a more complex system for constructing layers of photographic multilayered materials is used (US-PS 3 620 747, US-PS 3620745, DE-OS 2322165, DE-OS 2421544, DE-OS 24230250. And DE-OS 2530645. At the same time, known DIR components are introduced into insensitive halogen-syringate layers of differently constructed combinations of layers of the color-forming element to improve the transfer of details and colors.  In addition to the DIR-component with thiospheric cleavable groups of high inhibitory action, US-PS 3617291 are known. DIR-components that contain heterocyclic imino-compounds or their precursors as detachable groups (US-PS 3617291).  Components contain benztriazolyl or nitrobenzimidazolyl residues or their derivatives.  Compared to DIR-components with thioester structures, these compounds have insufficient DIR-action and are not suitable for color correction.  In addition, the known DIR components are most often hydrophobied compounds and the usual inhibitory residues as cleavable groups are only rarely associated with hydrophilic color components.  Their introduction into photographic material is possible only through dispersing technology with the additional use of high-boiling solvents and wetting agents, which is more laborious than the introduction in the form of a solution.  The purpose of the invention is to provide the use of new DIR components to create a color photographic geshogen-silver multilayer material with very good sharpness, good color grain and good color reproduction, where the disadvantages of the known technical solutions are overcome, such as too low intra-layer interlayer effects due to very low proportion of DIR components in mixtures with other components or the use of a more complex layer of color in a photographic multilayer material, as well as the complexity of the preparation, buslovlenna complicated purification methods used, DIR-komp6nent.  In addition, the purpose of the invention is to reduce the effort in the production of halogen-silver materials through the use of such DIR-components, which are introduced in the form of water-alkaline solutions in halogen-silver color-photographic layers.  The invention is based on the task of finding new DIR components, which can be introduced in high concentrations to achieve active intralayer effects and which, when obtained, require little cleaning effort, show high stability in the photographic layer, in which small desensitizing effects or complete lack of and which can be introduced dispersions in aqueous alkaline solutions.  This goal is achieved by the fact that the I photosensitive color photographic halogen-silver, the material as a DIR-component contains a compound of the general formula c-. - / where K is a color-forming group, which contains an anti-diffusion residue and has, if necessary, a substituted acetylacetanilyl, 1-aryl-pyrazolone (5) -type, 1-naphthol or phenol structure and in which in the combination position the substituted leaving groups of the inhibitor are linked ; Z — atoms or groups of atoms to supplement a heterocyclic five- or six-membered ring, X — o, s, or NR; R is OR ,, -COOR,, RA is a hydrogen atom or an alkyl residue with 1-5 carbon atoms; R is a hydrogen atom, ammonium or a metal ion.  According to the invention, the yellow, purple and blue-green DIR components consist of a component part and a thioester or tautomeric thioimide leaving group.  Crucial to the photochemical action is the fact that the leaving group is a mercaptoazole or aazine or a benzo-condensation derivative, which contain a hydrophilic group R.  The offered DIR-components of horsvio are suitable for sharpness, colored grain and color rendition.  They can be taken up in relatively high concentrations in the halo-spherical layers with a fraction of up to 50% relative to the color component of the same spectral region of the dye that arises, and in some cases, as a single color-forming element, the DIR component can be added to the halogen-spine dispersion in quantities from 1 to.  100 g per 1 mole of silver.  When used in high concentrations, up to use as the sole color-forming element, the amount introduced is 30-100 g per 1 mole of silver halide.  In addition, it is possible to be combined with any other components, for example, colored, masking and colorless components, c. amounts of 1-30 g per 1 mole of silver.  Use in high concentrations provides a very good combination when high yields of the dye are achieved, above 50%, and at the same time many inhibitors of release are released, which entail intra- and interlayer effects.  There are excellent intra-layer effects in the corresponding layer that appear in the form of fine colored grains and high sharpness of the image.  Due to the high local concentration, after combination, many manifestation inhibitors may diffuse into adjacent layers.  Thus, the proposed DIR components make it possible, for example, to correct the side absorption of dyes in adjacent layers through an interlayer effect, with relatively simple construction of layers of color photographic material.  These advantages offered by the DIR-Component are due to the fact. that they contain mercaptoazoles, mercapto azines, or the corresponding benzocondensated derivatives, which have a hydrophilic group, RJ, as the thioether cleavable group.  .  Kinetic measurements show that a good combination associated with a high yield of dye, in comparison with the known DIR-components, is not based on high speed of mixing, but on the special inhibitory effects of hydrophilic substituted thioether cleavable groups contained in the proposed DIR-components .  These effects are largely independent of the type of component K in the general formulas 1 and I of the proposed DIR-gk penthe.  The data of the kinetic measurements are presented in Table. one.  Another advantage of using the proposed DIR-component is due to the fact that insignificant residues of the corresponding HenpeapauyH hydrophilic-substituted mercapto heterocycles, which are ossified after the DIR-kokfonent, were significantly less sensitive than in the case of DIR-components.  Therefore, less effort is required when cleaning the proposed DNR component.  In addition, the proposed DIR components have excellent stability in the photographic layer, and their sensitivity does not decrease due to the disproportionate exposure of the decomposition.  An advantage of the invention is also that new components are introduced into a photographic emulsion in the usual manner of dispersion, for example, 1261061 or as a solution.  Administration as a solution occurs in an alkaline medium in the presence of a dipolar aprotic solvent, for example, dimethylformamide (introduction examples 1-3).  The invention is not limited to the simultaneous use of other photochemical additives such as gelatin applicators, tanning agents and wetting agents, chemical and spectral sensitizers, stabilizers and anti-tampering agents, antioxidants, compounds for adjusting the pH value, etc. d.  In addition, the application of the proposed DIR component is not affected by the composition of silver halide, its crystalline structure and form, the substrate used, the composition of the binding agent, and the use of other adjuvants that are required for the manufacture of photographic halogen-siliceous multilayer materials.   The use of the proposed DIR-component in photographic material is possible in separate layers and / or in combinations of layers.  Some structures of new compounds, as well as melting points and yield, are presented in Table. one.  The examples given for the DIR-component with hydrophilic-substituted inhibiting cleavable groups in the position of the combination of the known yellow, purple and blue-green colored components do not limit the use of the proposed DIR-components.  The preparation is carried out according to synthesis examples 1-3 or the like.  The principle of the synthesis is to convert the alkali salts of hydrophilically substituted mercaptoazoles with the corresponding components, which are substituted by halogen in the combination position, in a dipolar aprotic solvent at temperatures of 50-150 ° C.  The synthesis of the necessary mercaptoazoles can be, for example, in the case of hydrophilically substituted mercaptoterazoles, given by DD-PS 90 625.  Kinetic measurements were carried out with the known DIR components 13 and 14, which were obtained, as a matter of fact, of synthesis examples in US-PS 3227551, and which contain the known 1-phenyltetra-el-5-yl-thio-residue as a leaving group, and the proposed compounds 7 and 10 with a hydrophilic substituent in the leaving group.  The reaction between the DIR components and the oxidation product, N, N-diethyl-para-phenylenediamine, was carried out in 25% aqueous C-propanol at.  The dye formation follows the second-order rate of reaction, and the reaction rate is determined by the rate constant K, the numerical value of which. is contained in table. 3  The reaction rates of compounds 13 and 10, as well as 14 and 7, which are related to the same type of component, differ only slightly and lie in the same range of values.  The proposed DIR-components do not possess an increased activity of the combination.  Comparative measurement results are shown in Table. 2, Example 1 synthesis, 4- 1- 3-Carboxyphenyl) -tetrazol-5-yl-mercato-1-hydroxy-2-naphthenate - 2-octadecylox-anilide (compound 1), 4.88 g (6.02 mol ; the sodium salt of 1- (3-carboxyphenyl) -5-mercaptotetrazole and 12.2 / (o, 02msec) 4-bromo-1-hydroxy-2-naphthate the iat (2-octalecyloxy) -anilide. 8 h in 200 ml of acetone under reflux.  The solvent is distilled off, the residue is taken up in 500 ml of boiling ethanol and filtered. hot solution from precipitated sodium bromide.  After 10 days of storage at a temperature between 0 and 10 ° C, Compound 1 crystallizes out.  The product is sucked off by rinsing with ethanol, cooled with ice and air dried.  Output: 4.9 g (once ethanol) 32 from the theoretical, t. square  134-135p.  Example 2 (synthesis).  3-Stearo-ylamino-4- (l-para-hydroxyphenyl-tetrazol-5-yl3-1-phenylpyrazolone- (5) -compound 4.  As in Example 1, 4.32 g (0.02 mol) of 1-para-hydroxyphenyl-5-mercaptotetra sodium salt is used.  ash from 9.52 g (0.02 mol) of 5-chloro-3-heptadecylcarbamoyl-1-phenylpyrazolone (5.  Output: 5.7 g (once ethanol), 45% of theoretical, t. square  164-166 C.  The required 5-chloropyrazole is prepared as follows.  To 44.16 g (0.1 mol of 3-stearoylamino-1-phenylpyrazolone- (5) e 500 ml of absolute methylene chloride is added dropwise at 0-10 ° C under stirring and with the exception of air humidity 9.5 ml solution (0.12 mol, D 1,667 r / cMj of sulphuryl chloride and 25 ml of absolute methylene chloride.  After the addition is complete, stir for another half hour, then heat # 1T for 4 h when using reverse holo. The solvent is distilled off and recrystallized once from methanol and once from acetone.  Yield: 24.4 g, 51.3% of theoretical, t. square  52-55 ° C.  Primerz (synth, ez).  2- (Para-lauroyl-1-metobenzoyl) -2- (1-para-hydroxyphenyltetrazol-5-yl-) mercapto- (ortho-chloro) -acetanate-LID - compound 2.  As in Example 1, 4.32 g (0.02 mol) of 1- (para-hydroxyphenyl) -5-mercapto-tetrazole sodium salt is used with 10.12 g (0.02 mol) of 2-chloro-2-para-laurylamino-benzoyl- (ortho-chloro) acetate. nilida  Yield: 6.1 (once metnol), 46% of theoretical, t. square  121-123 C.  As an exaggeration of the exact product, the corresponding 2-chlorobenzoyl-acetanilide was obtained by chlorination with sulphuryl chloride in methylene chloride by analogy with Example 2.  Output: 7.2 g (once ethanol), 76% of theoretical, t. square  .  The following examples of introduction show that, for example, the proposed DIR-component 7 as a solution in an alkaline medium and as a dispersant can be converted into a form that allows simple addition to a photographic emulsion.  Example 4 (introduction).  5.3 g (v, 01 mol) of compound 13 are dissolved with heating in 17.5 ml of ethyl acetate and 2.5 ml of dibutyl phthalate.  53 ml of a 10% aqueous gelatin solution and 10 ml of a 5% dodecyl sulfonate solution at 40-60 ° C are placed in the dispersant.  The solution components are poured when heated in a gelatin mixture and dispersed for 3 minutes.  Then ethyl acetate is distilled off in vacuo and the dispersant is stabilized: by adding 4 ml of a 4% aqueous solution of phenol.  The finished dispersion is cured and stored in the refrigerator until use.  PRI me R 5 (introduction).  7.87 g (0.01 mol) of compound 7 are dissolved, when heated, in 5 ml of dimethyl sulfoxide, 10 ml of methylene chloride, 5 ml of dibutyl phthalate and 10 ml of ethyl acetate and added to a solution of 79 ml of 10% aqueous gelatin solution and 15 MP 5% aqueous solution of dodecylsulfonate.  Further processing takes place according to Example 4 (introduction).  Example 6 (introduction), 7 ~ 37 g (0.01 mol) of compound 7 was dissolved in 6 ml of dimethylformamide at 50 ° C.  Under stirring, pour in 11 ml (0.022 mol) 2 n.  NaOH in this solution, if present, is contaminated, filtered and adjusted to the desired volume with water.  The following examples show the benefits of using the proposed D11P component.  For comparison, compound 13 (US-PS 3227551) is used as prior art.  Example, Highly sensitive bromo-iodo-silver with no a1 "1m emulsion, ripened with gold, with a silver content of 25 g / kg emulsion, iodide content of 6 mol. % and an average particle size of 0.6 μm are sensitized by the addition of 7-10 mol of 3-methyl-3-sulfoethyl-5. , 5-dimethyl-9-ethyl-benzithiotrimetin cyanine-betaine into 1 yol of silver and is divided into four parts.  Part A contains. 0.15 mol-1-hydroxy. -naphthenate-2- 2 - (- n-octadecyl-methyl-amine) -5-sulfo-2 anilide per 1 mole of silver and is indicated as type.  Part B contains 0.15 mol of the dinine 13 to 1 mol of silver and corresponds to the prior art.  Part B of the invention contains corjIacHo 0.15 mol of compound 12 per 1 mol of silver.  Part D according to the invention contains 0.15 mol of compound 8 per 1 mol of silver.  After the addition of the reflux powder, the emulsion is added to the carrier so that the silver content is 1 g / m. Then the samples are illuminated through a gray wedge factor 2) with red light and processed as follows. First order: color development for 7 minutes during washing 15 min at 12-15 Cg; bleaching 5 min at 20 s; spanning 5 min at.  12-15 C fix 5 min at. washing 15 min at 12-15 ° C. Color development: water softener 3, hydroxylamine sulfate}, 2, diethyl-I-phenylenediami sulfate 2.75; potassium carbonate 75, sodium sulfate 2} kg shgs 2 bromide, bring to 1 l with water.  Bleach bath, g: potassium cyanoferrate (lllj 40 potassium bromide 15; potassium hydrogen phosphate 25, bring to 1 l with water.  Fixative, g: sodium pentahydrate-thiosulfate 250} sodium tripolyphosphate 10, bring to 1 liter.  i.  Second order: color.  5 min at 35 ° C | washing for 1-3 min at 35 ° C} stop bath for 5 min while washing for 5 min while bleaching for 5 min while washing for 5 min with 35 fixative 5 min / with 35®Cj washing for 15 min at 35 ° C.  Color developer, g: sodium hexametaphosphate 3, hydroxylamine sulfate 1.2, diethyl P-phenylenediamine sulfate 1,4} potassium carbonate 50; sodium sulfate 1, potassium bromide 2 to bring water to 1 l.  Stop bath, g: sodium sulfate 7.5; sodium acetate 15, acetic acid concentrated 25, potassium sulphate aluminum, dodecahydrate 25; sodium thiosulfate 200 bring water to 1 l.  Bleaching bath and fixative as in the first order 1, Photographic data of samples A to D are given in Table. 3  From the data it can be seen that when using the proposed compounds 8 and 12, a much higher yield of the dye is obtained, as compared with the compound 13, corresponding to the state of the art.  Compound 12 is less sensitive than compound 13.  Example  Color photographic multilayer material T contains the following layers.  The composition of Example 7, part A, which is poured onto a substrate having an anti-riole layer on the emulsion side is used as the bottom layer.  Intermediate gelatinous layer.  For the middle layer, the same emulsion is used as in the lower layer / spectrally sensitized with the addition of 2.5 W 3 -bis-C-sulfato-ethyl-D-5, 5-diphenyl-9-ethyl-benzoxotrimetnciann-betaine per 1 mole of silver .  1 In addition to conventional additives, 0.12 mol of 1-phenyl11-3-stearoyl pyrazolone (5) is used for irrigation per 1 mole of silver as a purple component.  A yellow filter layer consisting of gelatin and colloidal silver.  In the upper layer, high-sensitivity bromo-iodo-silver on an emulsion with an average particle size of 0.7 µm is used, with an iodide content of 5 mol. % and a silver content of 27 g / kg emulsion.  0.16 mol of 4-stearoylaminobenzoyl acetate- is used as the yellow component. 2- (h, 5-carboxyl-phenoxy) -5-carbox -apilide.  Gelatinous coating.  The multilayer material 11 is constructed as 1, but in the lower layer, instead of the blue-green component, contains 0.15 mol of compound 12 per 1 mol of silver.  The silver content is 2 g / m.  Both materials are illuminated with a light color temperature of 3,200 K through a gray wedge (factor 2) and processed in a second order.  In tab. 4 shows photographic data.  to calculate the interlayer effect, the method described in DE-OS 2 509 722 is used.    ,,C 1. you

where UZ is the value of y for selective illumination, UU “is the value of y for white light.

The tl value is estimated from the lower to the middle floor. It constitutes 12% for a laminated material for a TI material of 17%.

For grain evaluation, the multilayer materials t and 1G are exposed to a density of 1 and appear.

Then graded-on-the-eye at 10x magnification. At the same time, it was possible to establish that the IT material is more fine-grained than the T material with the same sensitometric data (Table 4).

PRI me R 9. Photographic multi-layered material (1TI) is built in the same way as 1, but contains in the lower layer per mole of silver 0.15 mol of 1-hydroxy-naphthenate- (2) - C2- (n - octadecylmethylamino) -5-sulfo-anilide and 0.04 mol of compound 12 at 2 g of Ag H IN-Materials I and III are irradiated (C 200 k) and treated in nepBONty order.

Compared with material G, the IG material shows a desirable lowering of the gradient in the middle layer (Table 5) and an clearly improved I value, equal to 35% as compared with 2% for material 1.

Copies of the IIT material show improved color rendering compared to material I.

Example 10. The photographic multilayer material W is constructed as follows.

A combination of two layers consisting of a less sensitive layer closer to the substrate with an anti-real layer with a bromo-iodo-silver non-ammonia emulsion, ripened with gold, with an average grain size of 0.4 µm, silver content of 20 g / k emulsion is prepared as the bottom layer. and the iodide content is 4 mol. % and above is located in a layer with a more sensitive side of 4o-iodine-free ammonia-free emulsion with an average grain size of 0.6 µm, a silver content of 25 g / kg emulsion and an iodide content of 6 mol%.

Both layers are sensitized by adding 7–10 mol of 3-ethyl-3-sulfoethyl-5, 5-dimethyl-9-ethyl-benz-tio trimethium cyanine-betaine per mole of silver. The less sensitive layer contains 0.15 mol per mole of seber, more sensitive 0.04 nol of 1-hydroxy naphthenate- (2) (-octadecyl-methylamino) -5-sulfo-anilide. The silver content in both x- layers is about 0.7 g / cm

Intermediate gelatinous layer.

The middle layer is a combination of two layers. When used, emulsions correspond to an emulsion of the bottom layer. Both cobalt layers are sensitized with 2, 3,3-bis B-sulfatoethyl-5, 5-diphenyl-9-ethyl-benzoxotrimethine-cyanine-betaine. A less sensitive layer closest to the substrate contains 0.03 mol of 1-phenyl-3-stearylpyrazolone (li) -I and 0.06 mol of 1 - (- phenoxy-3 sulfo) -phenyl-3-stearoylamino-4-4-methylphenylsulfornyl ) -4-aminophenylazo -pyrazolone (5), a more sensitive layer contains 0.04 mol of 1-phenyl-3-stearyl-pyrazolone (5) per 1 mol of silver.

The photographic multi-layered material V is built as IV, but according to the invention, in the less sensitive composite layer of the lower layer, an additional 0.04 mol of compound 8 and in a less sensitive skim layer of the middle layer - an additional 0.03 mol of compound 4 per 1 mol of silver, with increasing content silver in the respective individual layers by 30%.

Materials are processed in first order. Photographic data are given in Table. 6

The interlayer effect for material IV in the lower to middle layer is 0%, and the material V is 10 and 11%, respectively.

Material V is finer grained and gives a copy with a better 1 color transfer than material IV

It is recognized as an invention according to the results of the examination carried out by the Office for the Invention of the German Democratic Republic.

Table 1

StsNga-SO-N

ni

C C-C-HH- 7

u

H

w

125-128 iH2N-OgS (30)

CO-tt-CiyHsa

164-166 (45)

96-103 (34)

-CO-NH-it-CigHas

.D

S02NH5

C18)

(42)

173-176

(24)

(2a)

Sequence tab. one

CO-NH-Ji-Ci, 5H55

25

CO6-n-Ci 57

S

N

SOjNa

jr /

ou CO-NH-tt-CuHjs

H-tl

SOjjNo

184.

10 C35)

CO-HH-tt-CieH s

one-.

v H-OH

Continued table. one

130

eleven

(42)

COO-B-CSigH 57

191-193

12

(21)

/ 3-he

 - --f

Nn

HE

co-ire-ft-CigHge

f

. ./cav I N-TVsOaMl, 4

table 2

CO-NH-Rj

N-it.

13

S - "- Ci2H26

1.4-10

# N-NX N /

ten

1.1-10

-S- n igHzs

O-p

14

Continued table. 2

2.9-10

-.

1,3-10

Ol-Smrl

Table 5

Claims (4)

1. LIGHT-SENSITIVE COLOR PHOTOGRAPHIC HALOGEN-SILVER MATERIAL WITH DIR-ENENTS, O characterized by the fact that as the DIR-component it contains a compound of the general formula I or II * 1 where K is a color-forming group that contains an anti-diffusion residue and has, if necessary, substituted acyl acetone -arylpyrazolone- (5) -o, 1-naphthol or phenol structure and in which, in the combination position, substituted cleavable corpses * of the inhibitor are connected; Z are atoms or groups of atoms to complement a heterocyclic five- or six-membered ring; X - 0, S or N B? R * - ^E 0y, -COOR ^J, -SOnNHR ^ OR. -SO, R '; R is a hydrogen atom or an alkyl residue with 1-5 carbon atoms ₃ ; R is a hydrogen atom, ammonium or metal ion. 2. The material according to claim 1, characterized in that the hydrophilically substituted inhibitory cleavable “group consists of 1-aryltetrazole - 5-yl-residual structure ΙΊΪ SU „, 1062640 and Rg have the indicated values Rf. 3. The material according to claim 1, with the fact that the DIR component is contained in an amount of 30-100 g per 1 mol of silver halide. 4. Material pop. 1, characterized in that in a mixture with other components of the DIR component contains 1-30 g per 1 mol of silver halide * ra.