DE2002378A1 - Color photographic developer and color photographic developing process - Google Patents

Description

PATCNTANWXITE DR. E. WIEGAND DIPL-ING. W. NIEAAANN 200.7378 DR. M. KÖHLER DIPL-ING. C GERNHARDT ^ά MÖNCHEN HAMBURG

\ TiUfON, 55547 «8000 MONKS 15,

TILEORAMMC. CARFATENT NUSSBAUMSTRASSEIO

January 20, 1970 .W. 14 651/70 13 / never

Fuji Photo Film Co., Ltd. Kanagawa (Japan)

Color photographic developer and color photographic Development process

The invention relates to color photography and particularly to a color photographic developing process using a color developer containing an improved yellow coupler.

In color photographic development, it is known to use such couplers obtained by reaction with the oxidation products of developing agents Based on aromatic primary amines, colored images form and there are many patents on this.

These couplers cause a coupling reaction with the oxidation product of an aromatic primary amine with the formation of dyes which are insoluble in water or conventional treatment solutions, whereby colored

00983371774

Images can be left in photographic emulsion layers. Such a coupler can be one Developing solution or a photographic emulsion layer can be incorporated before exposure and the improved Coupler according to the invention is of the type that is incorporated into a developing solution.

Color photographic development, the way in which couplers are incorporated into developers, is usually carried out by a subtractive color process and the couplers form cyan, Magenta and yellow dyes.

It is generally necessary that a useful coupler for color photography should contain a dye forms a desired spectral absorption behavior during development.

Among the couplers to be used for color photography, a yellow coupler is theoretical to form one Requires a dye that completely absorbs blue light and completely absorbs green light and red light lets through. However, many of the yellow couplers used hitherto are not adequately endowed with these properties. The yellow dye or color image is removed formed by subjecting the blue-sensitive layer to a reverse blue exposure after black-and-white exposure and then subjecting the layer to yellow color development, bleaching and fixing, wherein in In this case, such a phenomenon often occurs that the oxidation of the developed silver in the bleaching / procedure leaving behind reduced silver often '

009833/1774

is delayed and that further the silver is not completely removed in the fixing process, wherein the Silver remains in the yellow area (this phenomenon is called poor silver removing ability designated). The occurrence of poor silver removing ability deteriorates the transparency of the yellow image very considerable.

The object of the invention is to obtain a color photograph Development process according to which an ideal yellow image can be obtained. Another The awakening of the invention is the creation of a color photographic image Development process according to which a yellow color with an excellent spectral absorption behavior is formed and there is good silver removing ability.

These purposes can be achieved according to the invention, by adding a yellow coupler represented by the general formula shown below to a color developer

^Ro

COCH ₂ COHN

wherein R and R ¹ , which may be the same or different, each represent an alkyl group having 1 to 3 carbon atoms and X represents an alkyl group, aryl group or substituted aryl group.

0 09833/177

It is well known that benzoylacetanilide is useful as a yellow coupler, but using that of such a yellow coupler obtained has a low silver removing ability and worse in terms of spectral absorption behavior is.

It is also known that by introducing a substituent with an intramolecular hydrogen bonding function, e.g. one, methoxy group, in the o-position of the anilide nucleus of benzoylacetanilide the hue of the yellow Color image is improved (see Mees & James "The Theory of the Photographic Process ", 3rd edition, page 385). The compound benzoylaceto- (2-methoxy) -anilide is currently regarded as the most excellent yellow coupler, but it has such disadvantages that silver removing ability is poor and the yellow image thus formed has a reduced transmittance or transparency. if the group -NHSOpX »in which X has the meaning given above is introduced into the anilide core of benzoylacetanilide, the silver removing ability and can the water solubility of the yellow coupler can be improved, but the hue of the yellow image formed becomes reddish. To improve the hue, the simultaneous introduction of a methoxy group in the o-position is accordingly taken into consideration. However, if benzoylaceto-Jf2-methoxy-4- (4-toluenesulfonamide) J -anilide is even used, the yellow image formed is still reddish.

The substitution of the benzoyl nucleus by benzoylacetanilide is used as a further measure to improve the hue taken into consideration. If in this way an alkoxy group in the o-position of the benzoyl nucleus of Benzoylacetanilide is introduced, this shifts

009833/1774

2QO2378

Absorption ^ maximvim (Λ _max ) ^{to the} side of shorter wavelengths in order to obtain a desired hue, but the coupling ability of the coupler is reduced. The water-soluble ability of the coupler is greatly reduced. Moreover, when a 'alkoxy group is introduced into the p-position of the Benzoylkerns, the clutch capacity can of the coupler can be improved, although the desilvering ability is deteriorated, and the water solubility of the coupler is also "seriously degraded. In addition, in, the case of the introduction of an ^M ethoxy in den'Anilidkern, ZB when using · ■ A-Athoxybenzoylaceto-XS-methoxyO-anilide, the silver removal capacity is low and the water solubility of the coupler is also poor. The one -NHSOpX group in which X has the meaning given above on the anilide nucleus and at the same time on the alkoxy group on the benzoyl nucleus has the disadvantage that the color tone of the image becomes reddish in the o-position of the anilide nucleus of the latter compound, namely 2-methoxybenzoylaceto- £ 2-chloro- 4- (4-toluoisulfohamid) j-anilide, also a reddish-yellow one

On the other hand, it has been found that when an alkoxy group is in the o-position of the anilide core of benzoylacetanilide, an -NHSOgX ^ group, in which X has the meaning given above, in the 4- or 5-position thereof and at the same time an A * Lkoxy group in the 2- or 4-position of the benzoyl group are introduced, unexpectedly better results are obtained. This is how it will be

Q03833 / 1 774

Silver removing ability is improved, the water solubility of the coupler is also improved, and the absorption maximum of the color blue becomes on the side of shorter ones Wavelengths shifted to a desired hue and, moreover, the coupler is very excellent in coupling ability.

With reference to the drawing, curve A shows the spectral absorption curve of the color image (A) obtained by coupling a typical coupler used according to the invention, namely 4-ethoxybenzoylaceto-£ 2-methoxy-4- (4-toluenesulfonamido)] anilide obtained with the oxidation product of a color developer, namely 4-N, N-diethylaminoaniline; curve B shows the spectral absorption curve of the color image (B) obtained by coupling a control or comparison coupler, namely benzoyl, xydationsprodukt with the ^above the above-specified Fabentwicklers ;, the curve C, the spectral absorption curve shows the color image (C) , which was obtained by coupling a further control or comparison coupler, namely benzoylaceto- (2-methoxy) anilide with the oxidation product of the above-mentioned color coupler.

From the results shown in the graph it can be seen that using of the yellow coupler according to the invention, a lower undesired absorption in the green area and has a very good absorption behavior.

It was further confirmed that the coupler according to the invention had a preferable silver removing ability, as explained below. The silver removal capacity is given by the ratio of silver image density, j

009833/1774

measured using "a red filter, to the sum the densities of the color image and the silver image are measured using a blue filter, and is thus represented by the following equation:

Red density (Dr)

■ - 'ι ss numeric value

Blue density (Db)

This value is found in the color images corresponding to the spectral absorption curves shown in the drawing, in a color image (D) obtained by coupling a coupler according to the invention, namely 4-ethoxybenzoylaceto (2-methoxy-4-benzenesulphonamido) anilide the oxidation product of a color developer, namely 4-N, N-diethylaminoaniline, was formed on a color image (E) obtained by coupling 4-Äthoxyben2oylaceto- (2-methoXy-4-methanesulfonaittido ₄ ) _> -anilide with the above Developer had been formed, and measured on a color image (F) formed by coupling 4- * lthoxyben2oylaceto- £ 2-methoxy-5- (4-toluenesulfohamido) 3'-anilide with the above developer, and the The results obtained are shown in the table below.

\ ^V: -> _: .. ■■: ■■ <■■ - ■ < color image

Tabel 1 »0 2.0 0.5. 0.05 0.03 0.09 . 0.25 0.22 0.32 0.20 0.16 0.25 0.05 0.04 0.10 0.06 0.04 - 0.11 0.07 0.05 0.12

0 09 83 37 177

Note on the table:

* Color images obtained using the coupler according to the. Invention were obtained.

From the above results it can be seen that those used according to the invention Couplers have excellent silver removing properties. It is also clearly seen that a color image is obtained by the excellent silver removing ability is obtained with a good transparency and that the excellent silver removing ability in terms of ' Reproduction of a color photograph is very advantageous and inexpensive.

It is believed that the reason why the color image obtained with the coupler according to the invention has excellent spectral absorption properties and the coupler has very good silver removing ability is based on the specific chemical structure according to which the benzoylacetoanilide has an alkoxy group in the 2- or 4-position of the benzoyl nucleus and an alkoxy group in the 2-position of the anilide nucleus thereof and also has a sulfonamido group in the 4- or 5-position of the anilide nucleus.

The coupler according to the invention is used not only in natural color photography but also in monochromatic or dlchromatic photographic used.

Examples of the yellow couplers used in accordance with the invention are shown below:

009833 / 177Λ

Coupler 1

COCHgCOHK

NKSO ₂ CK ₃

Coupler 2

COCH ^ CGHlHf ^ -KKSO ₂ ^

OCHs V;

Coupler. 3

FCOCH ₂ COHN- ^ ^V > -. JSHSQ ₂

OCH,

Coupler 4

COOH ₂ COHN-

NHSO ₂ - ¹

CH ₃ '

OCH-

Coupler 5

- COCHyGOHN

Cm I

. OCH ^ V. ™

Coupler 6. · -.-. "

C ₂ H ₅ O - <(. Y- COGH ₂ COHN-V V- KKSO,

OCH ₃ 7, '· ..: ■

Coupler 7

Coupler 8

COHN

ί /

. OCjH ₇

Coupler 10

Coupler 11

Coupler 12

CoHM

Coupler 13

CH ₃

09833/177 4

Coupler

Coupler

. Coupler 16

6 CH ₃

Coupler 17

Coupler 18

V coupler 19 ^ \ -tocH *

Coupler 20

oc H $

OtH ₀

•. *

C * HH

■ - - a

009833/1774 CH *

Various examples relating to the preparation of the yellow couplers according to the invention are given below.

Manufacture 1;

(1 - a): Preparation of 4-methoxybenzoylaceto- (2-methoxy-4-nitro) -anilide: ■

A 1 liter three-necked flask was charged with 222 g of ethyl 4-methoxybenzoyl acetate, 168 g of 2- ^ ethoxy-4-nitroaniline and 250 ml of xylene, the flask being equipped with a stirrer, thermometer and tube for the distillation of Ethanol was provided. The mixture was heated to 140 to 150 ⁰ C in an oil bath with stirring and the ethanol byproduct was distilled off. After 1 hour, 85 % ethanol had distilled off. The reaction was stopped and 500 ml of methanol was added to the product to precipitate yellow crystals, which were then collected by filtration and washed with 300 ml of methanol to give 300 g of the above compound in the form of pure crystals having a melting point of 183 to 185 ⁰ C were obtained in a yield of 87 % .

(1 - b): Production of 4-methoxybenzoylaceto- (2-methoxy-4-amino) -anilide * hydrochloride:

A 2 liter three neck flask was filled with 300 g of the above 4-methoxybenzoylaceto- (2-methoxy-4-nitro) -anilide and prepared under preparation (1-a) 200 ml of dimethylformamide were charged and the flask was fitted with a stirrer, condenser and dropping funnel equipped and heated on a water bath to dissolve the above compound in the solvent.

009833/1774

to solve. Then, 500 ml of ethanol and 300 g of iron powder were added to the solution, and while adding 300 ml of concentrated hydrochloric acid through the dropping funnel, reduction was carried out. The reduction product was filtered and the filtrate was cooled and, after adding 500 ml of concentrated hydrochloric acid, further cooled, whereby the hydrochloride of the amino compound was precipitated. The crystals were collected by Piltratiai and washed in 300 ml of a 10% hydrochloric acid, whereby the above compound was obtained in the form of crystals in an amount of 230 g having a decomposition point of 215 to 218 ^° C. in a yield of 74 % .

(1 - c): Manufacture of the yellow coupler 1, ^ - benzoylaceto - ^ - methoxy ^ -methanesulfonamido ^ l-anilide:. .

A 500 ml three-necked Kolberi was charged with 35 g of the amino compound prepared above under the preparation (ib) and 300 ml of pyridine, and the mixture was stirred to break the amino bond, followed gradually by 11.2 g of methamsulfonyl chloride the solution while maintaining the temperature were added at 40 to 45 ⁰ C. The system was then reacted ^{at 50 to 60 ° C. for 1 hour.} After cooling, the product was added to ice water which had been acidified with hydrochloric acid to form crystals which were filtered, washed with water, dried and recrystallized from acetonitrile, with 21 g of the coupler having a melting point of 191 to 192 ^° C with a yield of 48 % .

09833/1774

Manufacturing 2:

Production of the yellow coupler 2; 4-methoxybenzoylaceto (2-methoxy-4-benzenesulfonamido) anilide:

The same procedure as given in Preparation (1-c) above was carried out using 35 g of the amino compound obtained in Preparation (1-b) above and 200 ml of pyridine and also 18 g of benzenesulfonyl chloride in place of that in Preparation ( 1-c) methanesulfonyl chloride used followed, with 23 g of the yellow coupler having a melting point of 180 ⁰ C with a yield of 50 % were obtained.

Manufacturing 3:

Production of the yellow coupler 3; 4-methoxybenzoylaceto- £ 2-methoxy-4- (4-toluenesulfonamido) J -anilide:

The same procedure as in Preparation (1-c) above was carried out using 35 g of the amino compound obtained in Preparation (1-b) above and 200 ml of pyridine, and also using 23 g of p-toluenesulfonyl chloride in place of that in Preparation (1-c) methanolsulfonyl chloride used, 27 g of the yellow coupler having a melting point of 205 to 206 ⁰ C with a yield of ^ 8% were obtained.

Manufacture 4;

(4-a): production of 4-ethoxybenzoylaceto- (2-methoxy-4-nitro) anilide: >

The above compound was used the same way of working as in production '

009833/1774

(ia) "described, with the modification that 236 g of ethyl 4-ethoxybenzoylacetate instead of ethyl 4-methoxybenzoylacetate, as used in preparation (ia), and 168 g of 2-methoxy-4-nitroanoaniline and 250 ml of XyIpI used to obtain 304 g of the above-mentioned compound having a melting point of 175 ° C at a yield of 85 %.

(4-b): Preparation of 4-ethoxybenzoylaceto- (2-methoxy-4-amino) -anilide · hydrochloride!

The same procedure as for preparation (ib) was followed with the modification that 304 g of the 4-ethoxybenzoylaeeto- {2-methoxy-4-nitro) anilide prepared above instead of the 4-methoxybenzoylaceto- (2 -methoxy-4-nitro) -anilids were used, to give 195 g of the above compound with a decomposition point of 209 ⁰ C at a Auebeute of 62.5% were obtained.

(4-c)! production of the yellow coupler 5} 4-ethoxybenzoylaceto- (2-methoxy-4-methanesulfonamido) -anilide:

The same procedure as stated above for preparation (1-c) was followed using 58 g of the amino compound prepared under (4-b) above, 200 ml of pyridine and 18 g of methanesulfonyl chloride, 37 g of the above-mentioned yellow coupler ers with a melting point of 189 ^° C. with a yield of 57 »5 % were obtained.

0 9 8 3 3/1774

Manufacture j ?:

Preparation of the yellow coupler, 6, '4-Äthoxybenzoylaceto- (2-methoxy-4-benzenesulfonamido) anilide:

The same procedure as set forth in Preparation (1-c) above was followed using 36.4 g of the amino compound prepared in Preparation (4-b) above, 200 ml of pyridine, and 18 g of benzenesulfonyl chloride, with 30 g of the above Couplers having a melting point of 169 ° C were obtained with a yield of 64 % .

Manufacture 6;

Production of the yellow coupler, 7j4-Äthoxybenzoylacetor2-methoxy-4- ( 4-toluene sulfonamido) [] - aenilide:

The same procedure as described in Preparation (1-c) above was repeated using 36.4 g of the amino compound prepared in (4-b) above, 200 ml of pyridine and 19 g of p-toluenesulfonyl chloride, yielding 23 g of the above-mentioned coupler with a melting point of 187 ⁰ C were obtained with a yield of 48 % .

Manufacturing 7:

(7-a): production of 4-ethoxybenzoylaceto- (2-meth- oxy-5-nitro) -anilide:

The same working process as in the manufacture (1-a) indicated, was made using 236 g of Ethy1-4-

009833/177 /;

ethoxybenzoylacetate and 168 g of 2-methoxy-5-nitroaniline instead of ethyl-4-methoxybenzoylacetate and 2-methoxy-4-riitroaniline, as used in (ia) above, followed, whereby 304 g of the above compound with a melting point of 205 to 206 ° C were obtained with a yield of 85 % .

(7-b): Preparation of 4-ethoxybenzoylaceto- (2-methoxy-5-amino) -antLid ^# hydrochloride:

A 3-liter three-necked kebab was charged with 154 g of the nitro compound obtained in (7-a) above and 600 ml of dimethylformamide, and after equipping with a stirrer, a condenser and a dropping funnel, the system was heated on a water bath with stirring to to solve the nitro compound. After further adding 500 ml of ethanol, 154 g of iron powder and then gradually. Adding 300 ml of hydrochloric acid, the resulting mixture was boiled for 30 minutes to effect reduction. The system was filtered while hot to remove excess iron powder, and the filtrate was mixed with 500 ml of hydrochloric acid, followed by cooling. The white crystals thus formed were collected by filtration, washed with water acidified with hydrochloric acid and then with acetonitrile, whereby 100 g of the above-identified compound having a decomposition point of 202 ° C. was obtained in a yield of 74 % .

0098 33/1774

(7-c): Preparation of yellow coupler 10; 4-ethoxybenzoylaceto- (2-methoxy-5-methanesulfonamido) anilide:

The same procedure as described above under Preparation (1-c) was repeated using 55 g of the amino compound prepared under (7-b) above, 17 g of methanesulfonyl chloride and 200 ml of pyridine, 27 g of the yellow coupler having a melting point of 207 ⁰ C bdi a yield of 44.5 % were obtained.

Manufacturing 8:

WsteELung of the yellow coupler 11; 4-Äthoxybenzoylaceto- (2-methoxy-5-benzenesulf onamido) anilide:

The same procedure as described in preparation (1-c) was repeated using 25 g of the amino compound obtained above under (7-b), 12 g of benzenesulfonyl chloride and 150 ml of pyridine, 12 g of the yellow coupler having a melting point of 191 ⁰ C were obtained with a yield of 46 % .

Manufacturing 9;

Preparation of the yellow coupler 12; 4-ethoxybenzoylaceto-£ 2-methoxy-5- (4-toluenesulf onamido yj-anilid:

The same procedure as described above for Preparation (1-c) was repeated using 55 g of the amino compound prepared under (7-b) above, 25 g of p-toluenesulfonyl chloride and 200 ml of pyridine, 35 g of the yellow coupler with a Melting point of 201 to 202 ⁰ C with a yield of 48.5 % were obtained.

009833/17 7

Manufacture 10; .

(10-a): Preparation of 2-methoxybenzoylaceto- (2-methoxy-4-nitro) -anilide:

The procedure described above for preparation (1-a) ■ was repeated with the modification that ethyl 2-methoxybenzoyl acetate was used in place of the ethyl 4-methoxybenzoyl acetate used in (1-a), 310 g of the above compound with a Melting point of 170 to 172 ⁰ C with a yield of 90 % were obtained.

(10-b): Preparation of 2-methoxybenzoylaceto- (2-methoxy-4-amino) anilide · hydrochloride

The same procedure, ^w h ^e above, in preparation (1-b), was evaluated using 310 g of the nitro compound obtained above in (10-a), 210 ml of dimethylformamide, 550 ml of ethanol, 310 g of iron powder and 550 ml of concentrated hydrochloric acid repeated, with 250 g of the above-mentioned compound with a decomposition point of 150 ⁰ C-at. a yield of 79 % were obtained.

(iO-c): Production of the yellow coupler 13; 2-Hethoxybenzoylaceto - ^ - methoxy-4 ^ methanesulf onamido) anilide:

The same. Procedure as described above in Preparation (1-c), using 35 g of the amino compound obtained in (10-b) above, 200 ml of pyridine. and 11.4 gi% thanesulfonyl chloride followed, with 21 g of the yellow coupler having a melting point of 172 ⁰ C with a yield of 54 $ 6 were obtained.

009833/177

Manufacturing 11:

Preparation of the yellow coupler 1 ^ 2-methoxybenzoylaceto- (2-methoxy-4-benzenesulfonamido) anilide:

The same procedure as in Preparation (1-c) was repeated using 35 g of the above errhaltenen in (10-b) amino compound, 200 ml of pyridine and 18 g Benzolsulf onylchlorid followed using 25 g of the yellow coupler having a melting point of 181 ⁰ C were obtained with a yield of 55 % .

Manufacture 12:

Production of the yellow coupler ^^ - Methoxybenzoylaceto- £ 2-methoxy-4- (4-toluenesulfanamido) ~ \ -anilide:

The same procedure as given in Preparation (1-c) above was carried out using 35 g of the amino compound obtained in (10-b) above, 200 ml of pyridine and 19 g of p-toluenesulfonyl chloride to obtain 28 g of the yellow coupler having a melting point of 130 ⁰ C were obtained with a yield of 60 % , repeated.

Manufacture 1;?:

(13-a): Preparation of 2- ¹ ' ¹ ethoxybenzoylaceto- (2-methoxy-5-nitro) -anilide:

The same procedure outlined in Preparation (1-a) above was followed using ethyl 2-methoxybenzoyl acetate and 2-methoxy-5-nitroaniline instead of ethyl 4-methoxybenzoyl acetate and 2-methoxy-4-nitro ~ aniline, as used above under (1-a), repeated,

009833 /

237 g of the above-mentioned compound having a melting point of 163 to 164 ^° C. were obtained with a yield of 79 % .

(13-b): Preparation of 2-methoxybenzoylaceto- (2-methoxy ^ 5-amino) anilide; hydrochloride:

The same procedure as specified in preparation (ib) was repeated using 237 g of the nitro compound obtained above under (i3-a), 150 ml of dimethylformamide, 400 ml of ethanol, 237 g of iron powder and 400 ml of concentrated hydrochloric acid, with 212 g of the abovementioned compound with a decomposition point of 191 ^° C. and a yield of 75 % were obtained.

(13-c): Preparation of yellow coupler 16; 2-methoxybenzoylaceto- (2-methoxy-5-methanesulfonamido) anilide:

The same procedure as given for preparation (1-c) was repeated using 35 g of the amino compound prepared in (13-b) above, 200 ml of pyridine and 11.4 g of methane-sulfonyl chloride, 28 "g of the yellow coupler being used A melting point of 155 ^° C. was obtained with a yield of 57 % .

Manufacture 14; ■■ ..

Preparation of the yellow coupler 17 i 2-methoxybenzoylaceto- (2-methoxy-5 ⁱ -benzenesulfonamido) anilide:

The same procedure as indicated for preparation (1-c) was repeated using 35 g of the amino compound prepared above under (13-b), 200 ml of pyridine and 18 g of benzenesulfonyl chloride, 31 g of said yellow cooler having a melting point of 177 ⁰ C were obtained with a yield of 56%.

0 098 3 3/177 U

The invention is explained in more detail below with the aid of examples.

example 1

A gelatin-iodobromide silver emulsion which had not been subjected to color sensitization (a blue-sensitive emulsion for a color photographic Element such as being developed in developers containing couplers) was applied to cellulose acetate film upset. After exposing the photosensitive film to a wedge exposure using a sensitometer of the NSG type, the film became the following photographic Subject to treatments:

Black z-white development 2 & ° C 5 Water wash 2 '

Reverse blue exposure '200 CMS.

Yellow color development 5 '

Water wash 2 '

Bleach 2 '

Water wash 2 '

Fixation 2 ■

Water wash 2 *

The composition?' ¹ C ^ r treatment solutions described above are given below:

Black and white developer

N-methyl-p-aminophenol sulfite 20 g

Sodium sulfite 90 g

Hydroquinone 8.0 g

Sodium carbonate, monohydrate 52.5 g

Potassium bromide 5 »0 g

Potassium thioxyanate 1.0 g

Water rest to 1000 ml

009833/1774

Yellow color developer

4-N _f N-diethylaminoaniline sulfite

Sodium sulfite Potassium bromide Potassium iodide (0.1 # aqueous solution) Sodium sulfate

4-ethoxybenzoylaceto ^ 2-methoxy-4- (4-toluenesulfonamido) 7-anilide (Yellow coupler 7)

Sodium hydroxide Water, rest on Bleach solution Potassium ferricyanide Potassium bromide '

borax

Boric acid

Water rest on Fixing solution Sodium thiosulfate Sodium sulfite Water rest on

By doing this, a positive image of a yellow color with an absorption maximum was obtained obtained at 438 m / u and with a very good transparency. The spectral absorption curve of the color image is in the drawing using curve A, as indicated above ben, shown.

Example 2

The same procedure as given in Example 1 was repeated with the modification that 4-ethoxybenzoyl

• 3.0 G 5.0 ε 1.0 G' 5.0 ml 20.0 G 1.0 G 2.5 G 1000 ml 100 G 20th G 2 * 0 G 1.0 G 1000 ml 150 g 10 g 1000 ml

0 09833/177

aceto- (2-methoxy-4-methanesulfonamido) anilide (yellow coupler 5) was used instead of the coupler used in Example 1
became. The result was a positive image of yellow color with an absorption maximum at 441 m / u and with
get a very good transparency.

Example 5

The same procedure as used in Example 1,

was repeated with the modification that 4-Methoxybehzoylaceto- ^ ~ 2-methoxy-4- (4-toluenesulfonamido27-anilide
(Yellow coupler 3) instead of that used in Example 1
Coupler was used, giving a positive picture of
yellow color with an absorption maximum at 442 m / u
and was obtained with a very good transparency.

Example 4

The same procedure as used in Example 1 was repeated with the modification that 2-methoxybenzoylaceto- (2-methoxy-4-benzenesulfonamido) anilide (yellow coupler 14) was used in place of the coupler used in Example 1, with a positive image of yellowish color
with an absorption maximum at 408 m / u and with a
very good transparency received.

Example 5

The same procedure as used in Example 1 was repeated with the modification that 2-methoxybenzoylaceto- (2-methoxy-5-methanesulfonamido) anilide (Yellow coupler16) was used in place of the coupler used in Example 1 was taking a positive image of yellow color with a

009833/177

Absorption maximum at 428 m / u and with a very good one Transparency was obtained.

Example 6

It has the same operation as detailed in Example 1 using the G _e lbfarbentwicklers the following composition:

Yellow color developer .

Sodium sulfate

Potassium bromide

Sodium sulfite

Potassium iodide (0.1% aqueous solution) Sodium hydroxide (10 # aqueous solution) Hexylene glycol

4-A'thoxybenzoylacetO- (2-methOxy-5-benzenesulfonamido) anilide (Yellow coupler.11) 4-N, N-diethylaminoaniline sulfite i-phenyl-3-pyrazolidone

Water rest on

In this way of working, yellow color with an absorption maximum at 442 m / u and get a very good transparency.

Example 7

The same working method as used in the example, was repeated with the modification that 4-ethoxybenzpylaceto- (2-methoxy-4-benzenesulfonamido) anilide (Yellow * coupler 6) was used as a coupler in color development, leaving a positive image of yellow color with an absorption maximum at 441 nyu and a very good one Transparency was obtained

0 098 33/1774

80 G 1 G 5 ml 16 ml 28 ml 20th 5 g 1, G 3 1 g O, ml 1000

Claims (12)

Claims Color photographic developer, characterized in that it has a developing agent on the Primary aromatic amine base and developer represented by the general formula given below - COCH ₂ COHN- OR ¹ contains where R and R ¹ , which can be the same or different} each represent an alkyl group having 1 to 3 carbon atoms and X represents an alkyl, aryl or substituted aryl group. 2) the color photographic developer according to claim 1, characterized in that it is a compound of the general formula given below as a coupler OR - COCHCOHN - / V NHSO ₀ X contains wherein R and R ¹ , which may be the same or different, each represent an alkyl group having 1 to 3 carbon atoms and X represents an alkyl, aryl or substituted aryl group. 009833/17 7 4 3) color photographic developer according to claim 1, characterized in that it is a connection as a coupler of the general formula given below RO - i. ■ * - COCH ₉ COHN - ( V NHSO ₉ X contains, wherein R and R ', which are the same or different each one alkyl group with 1 to 3 carbon atoms and X represents an alkyl, aryl, or substituted aryl group. 4) The color photographic developer according to claim 1, characterized in that it is a compound as a coupler of the general formula given below NHSO ₂ X RO -. \ v_ COCH ₂ COHN - .- / OR ¹ contains, wherein R and R ', which are identical or different, sin can each have an alkyl group having 1 to 3 carbon atoms and X represents an alkyl, aryl, or substituted aryl group. 5) The color photographic developer according to claim 1, characterized in that it is a compound of the general formula given below as a coupler NHSO ₂ X RO - '<"" \ - COCH ₉ COHN - _v ~ ^ \ OR ¹ 009 833/177 contains, wherein R and R ¹ , which can be the same or different, each represent an alkyl group having 1 to 3 carbon atoms and X represents an alkyl, aryl or substituted aryl group. 6) color photographic developer according to claim 1, characterized in that it is a compound consisting of the group of 4-methoxybenzoylaceto- (2-methoxy-4-methanesulfonamido) anilide as a coupler. 4-methoxybenzoylaceto- (2-methoxy-4-benzenesulfohamido) -anilide, 4-methoxybenzoylaceto- ^ ~ 2-methoxy-4- (4-toluenesulfonamido, 27-anilide, 4-methoxybenzoylaceto / 2-methoxy-5- (4-toluenesulfonamido ) ⁷ ^ anilide, 4-ethoxybenzoylaceto (2-methoxy-4-methanesulphonamido) anilide, 4-ethoxybenzoylac etο (2-methoxy-4-benzenesulphonamido) anilide, 4-ethoxybenzoylaceto / 2-methoxy-4- (4 -toluenesulfonamido27-anilide, 4-ethoxybenzoylaceto / "" 2-ethoxy-4- (3,4-xylenesulfonamido27-anilide, 4-ethocybenzoylaceto _< / * 2-. propoxy-4- (4-ethylbenzenesulfonamido_} _> 7-anilide, 4 Ethoxybenzoylaceto (2-methoxy-5-methanesulphonamido) anilide, 4-ethocybenzoylaceto (2-methoxy-5-benzenesulphonamido) anilide, 4-ethoxybenzoylaceto </ "2-methoxy-5- (4-toluenesulphonamido J ^ -anilide, 2-methoxybenzoylaceto- (2-methoxy-4-methanesulfonamido) enilide, 2-methoxybenzoylaceto- (2-methoxy-4-benzenesuYonamido) -anilide, 2-methoxybenzoylaceto, 2-methoxy-4- (4-toluenesulfonamido27-anilide , 2-methoxybenzoylaceto- (2-methoxy-5-methanesulfonamido) -anilide, 2-methoxybenzoylaceto- (2-metho xy-5-benzenesulfonamido) -anilide, 2-methoxybenzoylaceto- / ~ 2-methoxy-5- (4-toluenesulfonamido27-anilide, 2-ethoxybenzoylaceto / 2-ethoxy-4- (4-toluenesulfonamido27-anilide and 4-propoxybenzoylaceto- (2-methoxy-4-benzenesulfonamido) anilide. 3/177 / » 7) color photographic development process, characterized in that an exposed photographic Halogen silver emulsion layer containing a developing agent based on a primary aromatic Amine in the presence of a coupler of the general formula given below RO COCH ₂ COHN - OR * where R and R ', the same or different can be, each an alkyl group having 1 to 3 carbon atoms and X represents an alkyl, aryl, or substituted aryl group. 8) color photographic development process, characterized in that the development in Presence of a coupler of the formula below - COCH ₂ COHN - <f ^ - NHSO ₂ X, ■ : r ^ OR ¹ in which R and R ¹ , which can be the same or different, each represent an alkyl group having 1 to 3 carbon atoms and X represents an alkyl, aryl or substituted aryl group, Q09833 / 17 7 4 9) color photographic development process according to claim 7, characterized in that the Development in the presence of a coupler of the general formula given below RO - *) - COCH ₂ COHN - ( ) - NHSO ₂ X in which R and R ¹ , which may be the same or different, each represent an alkyl group having 1 to 3 carbon atoms and X represents an alkyl, aryl or substituted aryl group. 10) Color photographic development process according to claim 7 »characterized in that the development in the presence of a coupler of the following given general formula _{/ 0} R {<> - COCH ₂ COHN - \ _ ■ ' OR ¹ in which R and R ¹ , which may be the same or different, each have an alkyl group; 1 ^to 3 carbon atoms and X represent an alkyl, aryl or substituted aryl group 009833/1774 11) Color photographic development process according to claim 7 »characterized in that the Development in the presence of a coupler of the general formula given below RO - (/ \> - COCH ₂ COHN τ executes «where R ¹ , which can be the same or different, each represent an alkyl group with 1 to 5 carbon atoms and X represents an alkyl, aryl or substituted aryl group .. 12) color photographic development process according to claim 7, characterized in that an exposed photographic halogen silver emulsion layer with a primary aromatic amine as coupler in the presence of a coupler from the group consisting of 4-methoxybenzoylaceto- (2-methoxy-4-methanesulfonamido) anilide, 4-methoxybenzoylaceto- (2-methoxy-4-benzenesulphonamido) anilide, 4-methoxybenzoylaceto- / 2-methoxy-4- (4-toluenesulphonamido ^ Z-anilide »4-methoxybenzoylaceto ^ 2-methoxy-5- (4-toluenesulphonamido2 ? anilide, 4-ethoxybenzoylaceto (2-methoxy-4-methanesulphonamido) anilide, 4-ethoxybenzoylaceto (2-methoxy-4-benzenesulphonamido) anilide _s 4-ethoxybenzoylaceto- ^ 2-methoxy-4- (4 ~ tol -olsulf onamido] _7T ^{! a} nilid, 4-Äthoxybenzoylaceto- / "2-ethox ^ -4- (3,4-xylenesulfonamiaa ^ - anilide, 4-ethoxybenzoylaceto- / 2-propoxy-4 * (4-ethylbenzenesulphonamido ^ Z -anilide, 4-ethoxybenzoylaceto- (2-methoxy-5-methanesulfonamido) -anilide, 4-ethoxybenzoylaceto- (2-methoxy-5-beneolsulfonamido) -anilide, 4-ethoxy- 0 0 9833/177 U benzoylaceto- _J / ~ 2-methoxy-5- (4-toluenesulfonamido27-anilide, 2-methoxybanzoylaceto- (2-methoxy-4-methanesulfonamido) -anilide, 2-methoxybQnzoylaceto- (2-methoxy-4-benzenesulfonamido) - anilide, 2-methoxybenzoylaceto- / ~ 2-methoxy-4- (4-toluenesulfonamido27-anilide, 2-methoxybenzoylaceto- (2-methoxy-5-methanesulfonamido) -anilide, 2-methoxybenzoylaceto- (2-methoxy-5-benzenesulfonamido) -anilide, 2-methoxybenzoylaceto - ^ "2-methoxy-5- (4-toluenesulfonamido27-anilide, 2-ethoxybenzoylaceto- _< f2-ethoxy-4- (4-toluenesulfonamido] / - anilide and 4-propoxybenzoylaceto- (2- methoxy-4-benzenesulfonamido) anilide. 009833/177