1-(2,4,6 - trichlorophenyl) -3- [2-chloro-5- (3 - octadecylamino) aniline] -4-(1-decyl-3,5 - dimethylpyrazol-4-ylazo) pyrazolin-5-magenta masking components for selenocysteine layer color negative photographic materials

 

(57) Abstract:

The use of the invention as Magenta masking components for selenocysteine layer color negative photographic materials. The inventive product- 1-(2, 4, 6-trichlorophenyl) -3-[2-chloro-5-(octadecylamino) anilino] -4-(1-decyl-3,5-dimethylpyrazol-4-ylazo) pyrazolin-5-he f-ly I BF BF52H72N8Cl4O3so pl. 90-92C, yield 40%. Reagent 1: 1-decyl-3,5-dimethyl-4-aminopyrazole. Reagent 2: NaNO2. Reaction conditions: in water in the presence of HCl at 0-2C. the Reagent 3: 1-(2, 4, 6-trichlorophenyl) -3-[2-chloro-5-octadecylamino) phenyl-amino] pyrazolin-5-it. Reaction conditions: in pyridine at 10-15C. table 2.

The invention relates to color components for selenocysteine negative photographic material, namely the new 1-(2,4,6-trichlorophenyl)-3-[2-chloro-5-(3-octadecylamino)aniline]- 4-(1-decyl-3,5-dimethylpyrazol-4-ylazo)pyrazolin-5-ONU formula I

CH = NNH

This connection can be used as Magenta masking components (H-688).

Known use as a Magenta masking components 1-(2,4,6-trichlorophenyl)-3-[3-(2,4-decret-amillennialism)benzylamine masking components 3P-62M is its low reactivity. In this regard, to achieve the effect of color correction you want to use it in relatively high concentrations compared to the main coupler component, which leads to lowering the sensitivity selenocysteine layer.

The aim of the invention is to increase the sensitivity selenocysteine layer of a color negative photographic material.

The objective is achieved by the use of the new compounds of formula 1.

The compound of the formula I get by the method similar by diazotization of 1-decyl-3,5-dimethyl-4-aminopyrazole and combined with 1-(2,4,6-trichlorophenyl)-3-[2-chloro-5-octadeca - nelsonseemed)aniline] pyrazolin-5 - one (component M-651).

The compound of formula I has significant advantages compared with the known masking component 3P-62M.

At its introduction in the silver halide emulsion in necessary to achieve color correction ratio with the main color-forming component of the observed increase in sensitivity selenocysteine layer.

P R I m e R 1. 2.6 g (0,011 M) 1-decyl-3,5-dimethyl-4-aminopyrazole dissolved in 10 ml of water and 1.2 ml of concentrated hydrochloric acid and deballasted diazonium salts is added dropwise to a solution 7,37 g (0.01 M) of 1-(2,4,6-trichlorophenyl)-3-[2-chloro-5-octadeca - dilaksanakan)phenylamino] pyrazolin-5-it in 60 ml of pyridine at 10-15aboutC, incubated for 3 h, diluted with twice the amount of water and the aqueous layer was separated. The precipitated oil is washed with water, add 50 ml of ethanol and heated to boiling, cooled to room temperature and the alcoholic solution is drained. The residue is recrystallized from ethanol and dried in air. Output - 4 g (40%), so pl. = 90-92aboutC.

Found, %: C 62,29; N? 7.04 Baby Mortality; N 11,07.

WITH52H72N8Cl4O3< / BR>
Calculated, %: C 62,46; N 7,21; N 11,21.

P R I m m e R 2 (analog). To 100 g bromooctadecane negative emulsion 3K-91 with microcrystals flattened octahedral shape ( =1,3 0,1, 78 g Ag met. 1 kg of the emulsion, of 5.1 mol. % AgJ, pH of 5.75, rvh=2,9), obtained by the method described in a single technological regulations N 272 for manufacturing the color negative films of CR-100 module-100 GHFP, 1989, add 3 ml of 1 % aqueous-alkaline solution of 5-methyl-7-hydroxy-1,3,4-triazinetrione (stabilizer f-1) and melt for 40 min at 38aboutWith, then injected 5 ml of 1% alcohol solution of 1,2-dioxybenzone (pyrocatechin), 14,5 ml of 0.05% alcohol solution of the spectral sensitizer 1,1,3-triethyl-3- -sulfopropyl-5,5-dicarboximide-betaine (1,6 10-4M/M AgHal) and dispersion, which contains a mixture of primary is] pyrazolin-5-he (3P-24) and Magenta masking components 1-(2,4,6-trichlorophenyl-3-[3-(2,4 - di-tert-amillennialism)benzoi a melamine] -4-(4-methoxyphenylazo) pyrazolin-5-he (3P-62M) at a molar ratio of between 2.5 to 1 and the total concentration of 5.0 10-2M/M AgHal.

The dispersion of the colored component is an emulsion of the type oil-in-water", which is prepared as follows: 1.73 g (2,58 10-3M) components 3P-24 and 0,83 g (1,03 10-3M) components 3A-62M dissolved in a mixture of 2.5 ml of tributyl phosphate and 5 ml of ethyl acetate at 60 to 65aboutC. To the resulting solution was injected with a mixture of 20 ml of 10% aqueous solution of gelatin and 4 ml of 4% aqueous solution of the surfactant sodium salt dodecylbenzensulfonate (SV-81) and disparut with an ultrasonic disperser. From the finished dispersion on a rotary vacuum evaporator to remove the ethyl acetate.

After dispersion of the colored component in the emulsion is injected additives for irrigation of 8 ml of 4% aqueous solution of surface substances sodium salt of di-hexyl ether sulfonterol acid (ST-102) and 10 ml of 3% solution of a tanning agent is monosodium salt of 2,4-dichloro-6-exitreason-1,3,5.

The emulsion is applied on triacetylcellulose substrate, student and dried.

The photographic layers exhibit in SENSITOMETRY CA-2M when the light source with a color temperature of 3200 K for yellow filter.

Chemical-photographic processing densitogram spend on the process MSB-2 (see. table. 1).

Mortar compositions. BR>
The color developing solution, g/l sodium Sulfite b/2

Manifesting substance DM-3 4 Antifog - 9 0,22 Bromide sodium 1,2 sodium Carbonate 25,6 sodium Bicarbonate 2,7 Water 850 ml

the pH at the 27aboutC = 10,2 0.02

Stop bath

Sulfuric acid, the oxygen - tarrawanna 10 ml Water up to 1000 ml

pH = 0,9 0,5

The bleaching solution, g/l

Potassium gelatine - modesty 40 Potassium bromide 16 Water up to 1 liter

pH = 6,5 0,5

Fixing solution, g/l sodium Thiosulfate 248 sodium Sulfite b/16.5 Metabisulfite sodium 2,8 Water to 1 liter

pH = 6,7 0,2

The spectral characteristics of the dye image was measured on a spectrophotometer with an optical density of about 1.0 at the maximum absorption (max).

Optical density fields densitogram measured on a photoelectric densitometer with a green filter. Basic sensitometric performance of the photographic properties of the emulsion layers is determined in accordance with GOST 9160-82. The effect of color correction or the effectiveness of the mask is determined by OST 19-64-76 (KwithC).

P R I m e R 3. Emulsion to water is prepared analogously to example 2, but in dispersion as a mask purple components using 1-(2,4,6-trichlorophenyl)-3-[2-'s quantities as component 3P-62M.

P R I m e R 4. Emulsion to water is prepared analogously to example 3, but the total content of the coupler and a masking component and tributyl phosphate in the dispersion is reduced by 1.5 times, resulting in a total concentration of a component in the layer is 3.33 and 10-2M/M AgHal at a molar ratio of between 2.5 to 1.

P R I m e R 5 (comparative). Melt 140 g bromooctadecane emulsion type-10 microcrystals correct octahedral shape ( =1,0 m, 55 g Ag met. 1 kg of the emulsion, 3 mol.% AgJ, pH=7,0, pBr=2,4), obtained by the method described in TR composition N 39 for manufacturing emulsions Negative-type 10". Further preparation for irrigation, obtaining the dispersion, the introduction of a component in the emulsion is carried out in accordance with example 2.

P R I m e R 6. Preparation of an emulsion for irrigation is conducted according to example 5, but in dispersion as a mask purple components use the connection formula I (H-688) in the same molar quantities that component 3P-62M.

Sensitometric and spectral data of the photographic layers is given in table. 2.

From the data table. 2 it is used as a mask purple connection components I obesity analogue 3P-62M when equal to their molar concentrations.

When using as a mask the components of compound I may reduce the total concentration of the component in the layer of 1.7-1.8 times, and thus reduce the thickness of the layer, while maintaining the advantages of high sensitivity.

1-(2,4,6-Trichlorophenyl)-3- [2-chloro-5-(3-octadecylamino)-aniline] -4-(1-decyl-3,5-dimethylpyrazol-4-ylazo)pyrazolin-5-it formula

< / BR>
as Magenta masking components for selenocysteine layer color negative photographic materials.

 

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EFFECT: valuable medicinal and biochemical properties of compounds and pharmaceutical compositions.

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