DEV0008145MA - - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

Date of registration: December 1, 1954. Advertised on December 20, 1956

GERMAN PATENT OFFICE

The invention relates to the production of photographic color images by color development, in particular using dye components for yellow.

It is known that in multilayer photographic material for producing the yellow image Derivatives of acetoacetic ester or benzoyl acetic ester can be used as dye components. In general, it must be required that a dye component, as an alkali salt, is readily soluble in water and that this solution can be kept for a long time. It also has high sensitivity and requires good coupling ability. . .. -. . ,.

It is already known that the solubility of benzoyl acetic ester derivatives can thereby be increased can that one or more ether-like bound in the phenyl nucleus of the benzoyl acetic acid ester. introduces dene substituents which may still carry hydroxyl groups. It is also not more new that diphenyl ether substituents a certain increase in the solubility of the components cause. .

The known yellow components, however, meet the requirements that one has with regard to solubility, the sensitivity and the coupling ability has to put on them, not. In particular is it is disadvantageous that the alkali salts of such components easily precipitate from their aqueous solutions. . '.' ■■. ■■■;. ■ .. ■;

Surprisingly, it has been found that apart from a considerable improvement in the solubility

609 737/318

Claims (1)

V 8145IVa / 57 b A strong increase in the photographic properties, in particular the coupling capacity, is also achieved when using components of the general formula. · _: .. - Ο - ΑΓΛ NH CO CH ₂ -CO-R ₁ wherein R is a solubility increasing group, e.g. B. COOH or SO ₃ H group, in any position of the ring, and R ₁ represents an alkyl or aralkyl group, is used, the 6derr by condensation of di-Aminodiphenyläthertricarbonsäüre ^J ■. · Trimethyl with acetoacetic acid derivatives and subsequent hydrolysis are obtained. The components according to the invention are distinguished from the known 'dye formers characterized by the fact that they are much better in watery Dissolve alkali and that their solutions are stable for a long time. Regarding their friendliness they surpass the well-known yellow couplers, considerably; because the blue sensitive layer of Multi-layer material can with such. Components more sensitive and also more steeply developed will. In particular, the steepening of the gradation curve of the yellow component in the upper casting has As a result, the color tones green, yellow-green and yellow in particular are significantly improved in their reproduction will. The yellow couplers for multilayer material have heretofore generally been made by the free aminocarboxylic acids with an acetoacetic ester derivative in a hydrocarbon, e.g. Toluene, condensed. Applying this known method to the color couplers according to the invention on, you will not get it in the desired quality. But if you have the di- or trimethyl esters of aminodiphenylether tricarboxylic acid used for condensation, color couplers with the specified properties are obtained. Example ι ^{1 mol of 4-aminodiphenyl ether 2} > 3 ''S'-tricarboxylic acid trimethyl ester and 0.95 mol of stearoyl acetic ester in 1500 ecm of xylene are added to a 3 liter flask with a short column and a descending condenser connected to it 150 to 165 ⁰ heated until no more alcohol distills off. The residue is saponified with a little more than the calculated amount of alcoholic 10% sodium hydroxide solution, the sodium salt which precipitates is filtered off with suction, dissolved in water and the component is set free by acidification. It is recrystallized from methanol. F. 198 to 202 ⁰ . B e i s ρ i e 1 2 As in Example 1 ', 4-aminodiphenyl ether-2, 2', 4 ^/ -tricarboxylic acid dimethyl ester is reacted with stearoyl acetic ester. F. 179 to 183 ° .. Example 3 ■ v ^.-: .- y: is reacted as in Example 1 ^ ■ '-Aminodiphenyläther-4, 3', S'-tricarbonsäuretrime'thylester with Stearoylessigester um.i / F, 222-226 ^0th.:. Example 4 As in Example 1, 4-aminodiphenyl ether-2, 3 ', 5' -tricarboxylic acid trimethyl ester is reacted with p-octadecyloxybenzoyl acetic ester. The obtained product sinters at 200 and ⁰¹ melts with decomposition at 280 ^0th "" ■ '■ "■"' Claims: i. Process for the production of photographic color images by color development, characterized in that the dye components for yellow are compounds of the general formula > - 0— ' NH
CO
CH ₂ -CO-R ₁ wherein R is a solubility increasing group, e.g. B. a COOH or SO ₃ Η group, and R _{1 is} an alkyl or aralkyl group and the iodine by condensation of aminodiphenylether tricarboxylic acid di- or trimethyl ester with aoetoacetic acid derivatives and subsequent saponification: ■ were obtained. "2. Multilayer photographic material for performing the method according to claim i, characterized in that at least one of the layers has dye components the general formula CH ₂ -CO-R ₁ . wherein R is a solubility increasing group, e.g. B. a COOH or SO ₃ H group, and R _{1 is} an alkyl or aralkyl group. Considered publications: German patent specifications No. 884 151, 878890. © 609 737/318 12.56