CH620526A5 - Colour-photographic material with novel yellow couplers - Google Patents

Description

620526

2nd

PATENT CLAIMS 1. Color photographic material, characterized in that the yellow coupler of the formula

, '- 0.

"--0 '

0

Alkyl groups with at most 4 carbon atoms, phenyl groups or heterocyclic radical, where Rh and Ri2 or Rn and Ru or R12 and R13 together with 1 or 2 carbon atoms of ring 1 can form a 5- to 6-membered carbocyclic ring and wherein consistently mean at least 2 of the characters R11 to Ru are hydrogen atoms.

4. Color photographic material according to claim 1, characterized in that the yellow coupler of the formula

0 G

in which G is a yellow coupler residue bonded to the oxygen atom by the active methylene group and Z is the addition to a residue with the six-membered ring consisting of the phosphorus atom, the two oxygen atoms and three carbon atoms.

2. Color photographic material according to claim 1, characterized in that the yellow coupler of the formula

/

R,

20th

R

R

7

XC / \

c-0

[(H_) 7-p-q-r

[(R2lVl -

[^ 22 ^ -1 _ [^ r-l

X

0

A

C P.

'\ / \

/ c \

H

R,

C-0

H

0

in which G has the meaning given, R21, R22 and R23 each represent an alkyl radical having at most 4 carbon atoms and p, q and r each represent one of the numbers 1 and 2.

5. Color photographic material according to claim 1, characterized in that the yellow coupler of the formula

30th

in which G has the meaning given and of the five characters Ri, R2, R3, R4 and Rs their 2 to 5 hydrogen atoms, their 1 to 3 alkyl groups each having a maximum of 4 carbon atoms, their 1 to 2 halogen atoms, acylamino groups, Pen, benzene residues, aralkyl residues directly or via an oxygen or sulfur atom to alkyl groups bonded to carbon atoms of the ring with a maximum of 4 carbon atoms, benzene residues or heterocyclic residues or their two 10 bonded to the same carbon atom of the ring or to two adjacent carbon atoms of the ring together with these Carbon atoms a carbocyclic,

mono- or bicyclic ring forming radical.

3. Color photographic material according to claim 1, «characterized in that the yellow coupler of the formula

H H \ / _

153 /

xc / \

R

34

C -

/ \ H H

\ / / \

G

R

^ 2 / Rll

° \ / P.

where G has the meaning given, R33 represents a hydrogen atom or an alkyl group having a maximum of 4 carbon atoms and R34 represents a hydrogen atom, an alkyl group having a maximum of 4 carbon atoms, an alkoxy group having a maximum of 4 carbon atoms, a phenyl group, a benzyl group or a phenoxy group.

6. Color photographic material according to one of claims 1 to 5, characterized in that the rest G of the formula

\ 3 / c '

/C\.-oA

- G

R

55

14

/ \ l15

R, r H

/

CH

0

Ii c-Q

/ L1

where G has the meaning given, Rn, R12 and R15, independently of one another, hydrogen atoms, alkyl group with a maximum of 4 carbon atoms, phenyl or benzyl groups, Rn and Ru, independently of one another, hydrogen atoms, fluorine atoms, alkyl groups with a maximum of 4 each Carbon atoms, acylamino groups derived from lower fatty acids, heterocyclic radicals or bound to the carbon atom of the ring by oxygen or sulfur atoms

60 C -N

11 XL

0 2

in which Q is an alkyl group having 1 to 32 carbon atoms, an alkoxyalkyl group having 2 to 32 carbon atoms, a cycloalkyl radical, an aryl radical or a heterocyclic radical, the latter two having alkyl or alkoxy groups containing 1 to 18 carbon atoms,

3rd

620526

Halogen atoms, acylamino groups, sulfonamide or optionally containing 1 to 5 carbon atoms

Carboxylic acid groups can be further substituted, Li is an alkoxy group, chlorine atoms, an acylamino group, a

Hydrogen atom or an alkyl group with 1 to 5 carboxylic acid amide group and / or carboxylic acid ester group

Substance atoms and L2 represent an alkyl group with 1 to 18 carbon-substituted benzene radical, one of the sub-

atoms or one with 1 to 18 carbon atoms, if necessary, can be one of the usual ballast groups,

men containing alkyl or alkoxy groups, halogenato 8. Color photographic material according to one of the men, acylamino groups, sulfonamide groups, carbon claims 1 to 5, characterized in that the rest G

acid amide groups and / or carboxylic acid ester groups further- the formula substituted benzene.

7. Color photographic material according to one of the 10 0 CHo

Claims 1 to 5, characterized in that the rest G III

of the formula c

II '5 / cr

-ch3

• c - q.

vn ^

CH 3

H

~ C ^ / H -C_N

C- N 20 II

ö h os, in which L3 has the meaning given in claim 7, in which Qi has an alkyl group having 1 to 8 carbon atoms.

Atoms or an optionally with 1 to 5 carbon atoms. 9. Color photographic material according to one of the men containing alkyl or alkoxy groups or with one of claims 1 to 5, characterized in that the rest G

Acylamino group further substituted benzene and L3 one of the formula

9? H3? 2H5

- CH

—C — CH3 H ^ C — c — Cll3

CH0

0

where m is 1 or 3.

NH —- C - {• CH 2 *) "^ - 0- C— C2H5

çh3

'c-nh-v n) 0 chj

As is known, exposed silver halide emulsion layers, which also contain color couplers, are developed with an aromatic developer substance containing primary amino groups to produce color photographic images. The oxidized developer substance then reacts with the color coupler to form an image dye, the amount of which depends on the amount of incident light.

In general, a multilayer photographic light-sensitive material is used which consists of a red-sensitive layer containing the cyan coupler, a green-sensitive layer containing the magenta coupler, and a blue-sensitive layer which in turn contains the yellow coupler. During the color development 6o the corresponding dyes with the colors teal, purple and yellow are created.

Phenols or a-naphthols are usually used as cyan couplers, pyrazolones as magenta couplers and acylacetylamides as yellow couplers. The dyes formed after development 65 are then indophenols, indamines or azomethines.

Conventional color couplers have an active methylene group, four equivalents of silver halide are required to convert them into the corresponding image dye; therefore such color couplers are called four-equivalent couplers. Color couplers are also known in which a hydrogen atom of the active methylene group is replaced by a group which can be split off during the coupling reaction. In this case, two equivalents of silver halide are required to produce the corresponding image dye. Such color couplers are therefore referred to as two-equivalent couplers.

Two-equivalent couplers have the following advantages over the four-equivalent couplers:

1. Your clutch speed is higher, which is particularly important in modern processing methods (three-wheel processing).

2. The amount of silver halide required for the formation of the same amount of dye is only half as large, which noticeably reduces the production costs for a photographic material.

3. The photosensitive layer can be kept thinner, which improves the sharpness and resolution of the color image obtained.

620526

4th

4. The sensitivity of the lower layers is increased due to the increased light transmission of the upper layers, which can be kept thinner.

With the yellow couplers, the following leaving groups in two-equivalent couplers have essentially been proposed to date:

- Halogen atoms, such as. B. in DE-OS 2114 577, FR-PS 991453 and 869 169 or US-PS 2,728,658 and 3,277,155;

- The group -OR, where R is alkyl, aryl, a heterocyclic radical or acyl, as for example in GB-PS 1 092 506; FR-PS 1 411 385 and 1 385 696 or in US-PS

3,447,928 and 3,408,194;

- the -SR "group described in GB-PS 953 454 or US-PS 3 265 506;

- The 1,2,3-benzotriazolyl group of the formula

- Leaving groups of the formula

S \

N N u \ /

10 V V '

wherein V together with the -C = C grouping forms an aromatic ring of the benzene series or a heterocyclic ring with at least one nitrogen atom (DE-OS 2 414 006). 15 These previously known two-equivalent couplers, however, tend either to pronounced fog, z. B. when storing the unprocessed material, especially in warm and humid storage, or the cleaved residues adversely affect the photographic properties. It is therefore an object of the present invention to produce new color photographic materials which largely overcome these disadvantages.

The object according to the invention is achieved by using new yellow couplers. The present invention therefore relates to a color photographic material which contains a yellow coupler in at least one layer, characterized in that the yellow coupler has the formula

(DE-OS 1 800420)

the residues -SOsH and -SCN (GB-PS 638 039; US-PS 3 253 924)

- Imide groups of the formulas or

0

ii

-N Q

M

0

(DE-OS 2163 812.2 213 461.2 057 941); - Remains of the formula

0

ii

-N Q

\ J

so/

/

X-Y

-N

N.

c- = c / \

R1

(DE-OS 2 329 587).

- Leaving groups of the formula

0

m

-N Z

ny ^

Rr

(DE-OS 2 433 812)

CD

35

'- ° «v / ° \ #

Z P

v- 0 0-

in which G is a yellow coupler residue bonded to the oxygen atom by the active methylene group and Z is the addition to a residue with the six-membered ring consisting of the phosphorus atom, the 40 two oxygen atoms and three carbon atoms.

For example, the yellow couplers correspond to the formula

45

50

(2)

R

R,

R2

3 \ / / \

R,

-O

0

0 G

c — o R ^ XH

where G has the meaning given and of the five characters Ri, R2, R3, R4 and R5, their 2 to 5 hydrogen atoms,

whose 1 to 3 alkyl groups, each with a maximum of 4 carbon atoms, whose 1 to 2 halogen atoms, acylamino groups, benzene residues, aralkyl residues, alkyl groups bonded directly or via an oxygen or sulfur atom to carbon atoms of the ring with at most 4 carbon atoms, benzene residues or heterocyclic residues or the two of which are bonded to the same carbon atom of the ring or to two adjacent carbon atoms of the ring together with these carbon atoms represent a carbocyclic, mono- or bicyclic ring.

5

620526

The yellow couplers of the formula genes of formulas (1) to (5) are particularly valuable, preferably residues of the following

Composition:

R-, n R,, radicals of the formula

1 ^ .LI

(3) n C 0S 0 5 0

13 C ts P (6) c Q

X

R14 „/ X ° —G ~ CÜ. .1.

C 0

R1r H

1

»Io C N

\ u \

Mr.

15 n 0 2

where G has the meaning given, Rn, R12 and Ris independently of one another, hydrogen atoms, alkyl groups with at most 4 carbon atoms each, phenyl or benzyl groups, R13 and Rm, independently of one another, hydrogen atoms, fluorine atoms, alkyl groups with at most 4 each Carbon atoms, acylamino groups derived from lower fatty acids, 20 heterocyclic radicals or alkyl groups bonded to the carbon atom of the ring by oxygen or sulfur atoms, each having a maximum of 4 carbon atoms, phenyl groups or heterocyclic radicals, where Rn and R12 or R13 and Rw or R12 and R13 together with 1 or 2 carbon atoms of ring I can form a 5- to 6-membered carbocyclic ring, and at least 2 of the characters R11 to R15 denote hydrogen atoms.

Yellow couplers further substituted by alkyl groups preferably correspond to formula 30

(4)

wherein Q is an alkyl group with 1 to 32 carbon atoms, an alkoxyalkyl group with 2 to 32 carbon atoms, a cycloalkyl radical, an aryl radical or a heterocyclic radical, the latter two having alkyl or alkoxy groups containing 1 to 18 carbon atoms, halogen atoms, acylamino groups, sulfonic acid amide or carboxylic acid groups may be further substituted, Li is a hydrogen atom or an alkyl group with 1 to 5 carbon atoms and L2 an alkyl group with 1 to 18 carbon atoms or an alkyl or alkoxy group, optionally containing 1 to 18 carbon atoms, halogen atoms, acylamino groups, sulfonamide groups, carboxamide groups and / or carboxylic ester groups are further substituted benzene radicals.

Remains of the formula

(7)

(H")-;

7-p -q-:

(R2l ~ Vl (R22 V-l

'<R23-> r-l

\ /

II

- O

c- / \

-0 v 0

-0 0-G

II

0

11

. c-

-ch c-

11

0

-N

/

H

J3

wherein G has the meaning given, R21, R22 and R23 each represent an alkyl radical with a maximum of 4 carbon atoms and p, q and r each represent one of the numbers 1 and 2.

The compounds of the formula are also preferred

H 11 \ /

R c 0 0

33s / \ //

(5) r ^ \

in which Qi is an alkyl group having 1 to 8 carbon atoms or an alkyl or alkoxy group optionally containing 1 to 5 carbon atoms or an benzyl radical which is further substituted by an acylamino-45 group, and L3 is an alkoxy group optionally containing 1 to 5 carbon atoms, chlorine atoms, an acylamino group, a carbon - mean acid amide group and / or carboxylic acid ester group further substituted benzene radical, where the acylamino group, the carboxylic acid amide group and carboxylic acid ester group can contain one of the usual ballast groups; Remains of the formula

34

C.

/ \ II H

-0

O

(8th)

0

u c-

CII "

I -J

-CH,

CIL,

bO

where G has the meaning given, R33 represents a hydrogen atom or an alkyl group having a maximum of 4 carbon atoms and R34 a hydrogen atom, an alkyl group having a maximum of 4 carbon atoms, an alkoxy group having a maximum of 4 carbon atoms, a phenyl group, a benzyl group or <, «a phenoxy group.

All yellow coupler residues (G) bound to the oxygen atom by the active methylene group contain the compounds

"CH

C-

u

0

where L3 has the meaning given;

/

II

-N

L.

620526

6

Remains of the formula

ÇUH

S ÇH3 H, for £ cîL

? -c «3 J I CH

3rd

CH C113 NH-C - (CH9) -0- /) -C-C'HS

/ "2 m \ —- / '2 5

.— / O CH.

Jt \

l3

C HN

wy o /

Gl where m is 1 or 3. have the following schematically recorded structures

The outgoing groups of the yellow couplers can have additional ring systems, for example:

\ _ o 0 v— 0 0

\ \ // \ X

0 0-

(10.1)

(10.2)

V 'x

- o

0-

° \

/ P \

0 o-

(10.3)

(10.4)

'v-o

0

/ \

-0 0-

//

0 0

xp ^

W V

(10.5) (10.6) (10-7)

As can be seen from formula (3), the carbon-55 possible stereoisomeries are taken into account, the following substance atoms of the phosphorinane ring expediently total substitution options:

at most three substituents. Here arise without the

> —O 0/0 0 Y 0 ß) 0 0

s' / v / y

S \ ^ \ S \ r \ c \

—0 0- 0 0- ~ 0 0 * - 0 ° "

(11.1) (11.2) (11.3) (11.4)

/ \

7

.620526

) 0

0

• ox V

r O 0

J \ ^

X p

\ —N '\

0 0-

v

0 0 \ ^

p

0 ^ X0-

0 0

V

oy Xo

(11.5)

(11.6)

(11.7)

(11.8)

-0 v 0

V

\ o 0-

\ o 0

\?

p

/ \

/ "0 0

(11..9)

'(11.10)

Examples of yellow couplers are those with the leaving groups of the following composition:

0 0

v *

p

/ \ 0 0-

0 2.1)

H 3 G

H3C

0 ti ni] n 0 0

u3n? \ / r \

c / V

(12.2)

ii3c-h2c p

o "V

(12.3)

h3c ~ h9c h3c-h2c co-bn

-0 v 0

p

./ \ -0 0-

(12.5)

H ~ 0

p

-0 0 -

(12.6)

iuc-h.c, ^ -ós x.o

3 2

/

/ P \

-Ox 0-

h3c- (h? c) 2

(12.7)

/ w

-c ° x °

\ —0 0-

(12.8)

° \

0 / PV

H3Ç ^ CH3

> —0 0.

H3C

(12.9)

° x

P

/ '\

-0

0-

(12.10)

(12.11)

(12.12)

620526

8th

O '0-

s \ / ° \ / —O

v0- (-p- H.c-O- <: i -0 '0- J \ -

(1.2.13)

(12.14)

(12.15)

0v ^ 0

yc

0 '

0-

° \ p ^ °

y xo f / V-o. .0

\ p ^

V-O ^ X0-

(12.16)

(12.17)

(12.18)

/ \

W ° -pf °

V.) -0y -0-

0. / O

(12.19)

(12.20)

(12.21)

The yellow couplers are appropriately provided with a so-called ballast group, which plays an important role when the coupler is dissolved in a high-boiling solvent which is not miscible with water and the solution is emulsified in the gelatin, which may contain 35 silver halides (so-called

protected couplers). The ballast groups should give the coupler the best possible solubility in the oily phase and reduce its tendency to crystallize.

The ballast groups customary for oil-soluble color couplers are generally known and are described in the relevant specialist literature. As such, they have no unexpected influence on the yellow couplers of the invention and correspond, for example, to the formulas

CIL

- C - CH - 0 C - C0II r

II I Y ^ / I 2

0 L

ClI.

113C — Ç - c.TJ

CIL

C— (CI10) 5— 0- / \ - C— C0H, -II z J \ W I z D

0

CIL

H0C— C - CH,

(13.1)

C2U5

(13.2)

C2ll5

(L: H, C ^ H, 11-CJ ^ 2 ^ 25 ^

• C-

I!

0

- (pi {\\\

U "2; 3 \ - /

\

C15H31

-IIN

H0 ,, C -0 2n + l n

(8 £ n 18)

(13.3)

(13.4)

9

620526

CH,

ct i -,

-N

cil I 'cil

_c _._ c_.o- / V-Ç — C9H

^ c7 \

l '

0

(13.5)

(L ': G12H25'

2 5

0 CIL

CIL

H ^ C-C-CH3

C18H35 'C18H37)

c2h5

(13.6)

■ o— (CH2) ll-ai3 0

(13.7)

-C-

0

., / 0- (CH2) 3-CH3

Ö 0— (CH2) 3-P'X

0- (CH2) 3-CW3

(13.8)

" H

O

(13.9)

0

o— (CH2) 3— p.

Ç? .Ll5

o - ci12—- cil - (ch2) y-- ch3

'0 —CII2— CM - (CH 2) J— CH 3

C2n5

0

/

o- (ch2) 3-p

I! / O- (cii2) t-ch3

■; -0

0

0 (CK2) j P ■

0 - (CII2) - CIl3 / 0- (CII2) 3-CII3

(13.10)

ô O-CCH ^^ - C ^

The ballast group is preferably bonded to the rest of the molecular part of the coupler via an oxygen or nitrogen atom, cf. Formula 20 and No. 14 to 19 of the table.

The compounds of the formulas (1) to (6) can be prepared by methods known per se, for example by adding a salt, in particular the potassium or silver salt of a cyclic acid ester of phosphoric acid of the formula

-0

(14)

-0

V

y

0

0 - m in which Z has the meaning given at the outset and M is a salt-forming cation, or, in the presence of an acid-binding agent, for. B. a base such as collidine, the acidic ester itself (M = H) with a compound of the formula

(15)

X G

implements b5, in which G has the meaning given and X represents a chlorine or bromine atom.

Acidic cyclic esters of phosphoric acid, or their salts are used here as starting materials

620 526

10th

already known, and moreover, these compounds can also be prepared by known methods. They are expedient by reacting dihydroxy compounds of the formula

(16)

-OH

OH

wherein Z has the meaning given, with phosphorus oxychloride and subsequent saponification of the acid chloride of the formula

O'/)

/

Z v

■ '0.

■ -0 '

0

p:

C.1

prepared (see also Houben-Weil, Methods of Organic Chemistry, 4th edition, Vol. 12/2, p. 276 and following). The chlorides of the formula (17) can also be prepared from the 2-chloro-1,2,3-dioxaphosphorinanes (op. Cit. P. 284) and the acids from the cyclic phosphites (Doklady Chemistry 196.28 [1971]) by oxidation.

As indicated at the beginning of the description, useful compounds are known as starting materials of the formula (15).

The compounds of the formulas (1) to (9) can be incorporated in a manner known per se as yellow couplers in photographic materials. As can already be seen from the above, they are expediently dissolved in a high-boiling, water-immiscible organic solvent and the solution is emulsified in a gelatin-silver-halide emulsion. Suitable coupler solvents are e.g. B. listed in US-PS 2 332 027, DE-OS 1 945 210 and DT-OS 2 140 309. Triaryl phosphates such as tricresyl phosphate and dialkyl phthalates such as dibutyl phthalate have proven to be particularly suitable coupler solvents.

Preferably, the yellow couplers are dissolved in the coupler solvent, optionally using an auxiliary solvent such as ethyl acetate or methylene chloride, and the solution is then, e.g. B. using ultrasound, emulsified in an aqueous solution of gelatin or another layer former usable for the production of photographic materials in the presence of a surfactant. The layer former can already contain the silver halide, or the aqueous emulsion of the coupler solution can be mixed with a so-called gelatin-silver halide emulsion. The emulsion of the coupler solution in gelatin obtained as described can also be processed into a material which contains the silver halide in a layer free of color couplers. Further additives such as hardener and light stabilizer can be incorporated into the solution of the coupler in the organic solvent, or the emulsion obtained therefrom.

The couplers can be mixed with one another or together with other known couplers in organic solvents and further processed in the manner indicated.

Otherwise, the further construction and also the processing of the color photographic material can be carried out in a conventional manner known per se. As is known, a p-phenylenediamine derivative is advantageously used as the developer substance.

The new yellow couplers of formulas (1) to (9) are characterized by various advantages. They are easily accessible, do not adversely affect the photographic development process 35 and result in photographic images with low fog.

example 1

45 g of l- (a-pivaloyl-a-bromoacetylamino> 2-chloro-5- [y-2,4-di-40 tertiaryamylphenoxy) butyrylamino] benzene of the formula

0 CH,

C-C-CIL

(18.1)

0

C ~ (CIl2-> y 0

? 2H5

CH.

C - C "H

2 5

CIL,

and 20 g potassium salt of the 2-hydroxy-2-oxo-l, 3,2-dioxaphosphorane of the formula

(19.1)

0 yo

'

0 ^ x0 ®

K

©

11

620 526

are refluxed in 350 ml of acetonitrile for 8 hours. The solvent is evaporated, the residue is heated with 100 ml of ethyl acetate, the whole is filtered hot and the Example 2 filtrate is diluted with 250 ml of methyl ether. After cooling and filtering, about 12 g of No. 1 yellow coupler from the 5 table are obtained as a white powder.

In an analogous manner, the compounds No. 5 and 12

of the table.

2 g of the pivaloyl compound of the formula (18.1) and 1 g of potassium salt of the 2-hydroxy-2-oxo-4,4,6-trimethyl-l, 3,2-dioxaphosphorinine of the formula

(19.2)

K

0

are in 25 ml of dimethylformamide for 8 hours at In an analogous manner, compound no. 3 is prepared.

22 ° C stirred. The reaction mixture is then 300

Poured ml of water and filtered the suspension obtained. 25 Example 3

After the residue has been chromatographed over a 1.8 g of l- (a-pivaloyl-a-chloroacetylamino) -2-chloro-5- [y- (2,4-di-

Column with silica gel and with benzene-ethyl acetate (17: 3) as tertiary amyl phenoxy) butyrylamino] benzene and 1.4 g of potassium

Superplasticizer gives yellow coupler No. 2 in the table as the salt of 2-hydroxy-2-oxo-5-ethyl-5-n-butyl-l, 3,2-dioxaphosphoric

White dust. nans of the formula

(19.3)

H C - * "3

H3C

- I10G

(112C) 3

% y <=>

• 0 0

k be refluxed with 50 ml of acetonitrile for 6 hours.

cooked. The resulting precipitate is filtered off. The compounds No. 6,7,8,9,

the residue obtained after evaporating the filtrate is 10, 11 and 13 to 19.

recrystallized from a mixture of ether and petroleum ether. The couplers No. 1 to 13 of the table correspond to the form

receives about 1.5 g of yellow coupler No. 4 of the table as a white 45 mei

(20)

/

y —en \

0

ii c ~

CIU I J

• c: - CH

I.

CIL

3rd

3 cl

HN— Ù \

0

0

"2" 5 U3C-C-CH3

CIL

HN - C - (CH2 ^ n ° -Q-? C2H5

CIL

620526

12

1

No.

Y

11

Melting point ° C

example

1

V-o ^ xo-

3rd

165-167

1

2nd

h3c ch3

C-0- <0-

I13C

3rd

159-160

2nd

3rd

H3V- ° ^ p ^ °

h3c / q /

3rd

176 - 1/7

2nd

4th

H.C-H0C

X ~ v

/ v — CT "0-H3C- (H2C) 3

3rd

135-140

3rd

5

HoC

t ° x °

X — 0 0-

3rd

184- - 194

1

6

^ —0 // xo-

3rd

225-226

3rd

13

620526

■

No.

Y

n

S ehm e1zpun kt ° C

example

7

/ v \ f ° \

V, .. / z \ —o 0 ~

3rd

172-173

3rd

8th

V „./ \ —0 ^ ^ 0-

3rd

co

0

1

00 -J

O

O

9

V-o ^ 'N-

3rd

190 • - 191

3rd

10th

/ 0 \

n c-o ~ (

\ —Er 0-

3rd

155

3rd

11

/ T "'\ / —0 \ ^ 0 (> - ° - \> <

W \ —0 0-

3rd

110-111

3rd

12

IUC

1 / ~ \ / ~ ° \ ^ °

H3c-H? C "fO-0-C0A0.

n3c

3rd

115-120

3rd

13

a r ° \ p ^ °

UloAo.

1

85-87

3rd

620526

14

No.

formula

S chine 1 z point cC

example

14

0 CiL, "

M i J

0 n C-C - CIL,

/ ° x sp / <3 / ch3

0-CH J

\ J \) ->

c HN- f s \

"\ -; / 0 1

0-C ~ 0- (CIT?) I; L-CH3

94-96

3rd

15

0 CH3

or C-C-CHL

5 V% - "0 / CH3

H.C- (H0C) ^ O7 x0-CH J Z 3 v C1

\ Jr ~ \? 2ll5 C-HN — C J HoC-C-CH «

ö 1 °? 2h5 l? h

HN-C-CH-0-C-C2H5

ch3

72

3rd

16

0 CH3 / 0vpr, 0 C-C-C1I3 M) '"\) - CH CH0 nl v J ui

^ K

C HN- f x)

0 1 0 (? H2) ll-CH3 ^? H

HN-C-CH-0 (3-C-C2H,

('; H3

117-121

3rd

15

620526

No.

formula

Melting point cc

example

17th

0 C1IQ

nr J

II c c-c-cn,

5 2w- 0 ^ 0 /. 3rd

X ^ p-x 'CHq h-c- (h9c) ~ "°" o-ch

3 2 y3 ^ Eq

C-HN- / ~ \

ö n ° (™ 2> irCH3 ^? H3

HN — C-CH 0 (% - C-C2H-

™ 3

resin

3rd

18th

0

0 HH-C- (CII2) 3-0-q o 5_A, x,

(>: <CH2) 14-CH3 \ -C) 0-CH

\ O-CHo

\ A

C HN ^ J> -Cl

0 l ~

II3C-0

3rd

19th

9 ÇH 0 HN-C- (CH?) 3 ~ o ~ -fj- C ~ C2H

c ~ f \ "1 ch3

/ H3C-C-CH3

H5CV p / C2H5

H3C- (H2C) 3 ~ ^ 0— «1

\ J ~ CH3 C HN- f ~ S ~~ Cl

M V = r /

0 1

IJ3C-0

5

3 3

620526

16

Example 4

76 mg of coupler No. 8 are dissolved in a mixture of 200 mg of tricresyl phosphate and 1.8 ml of methylene chloride, the methylene chloride is evaporated off, and 6.6 ml of a 6% gelatin solution, 1.2 ml of distilled water and 2 ml of an 8 % solution of diisobutylnaphthalenesulfonic acid sodium are added. The mixture is homogenized using ultrasound.

5.0 ml of freshly sonicated coupler emulsion, 3.3 ml of silver bromide emulsion with a pH of 6.5 and a content of 1.4% silver and 6.0% gelatin, 2.0 ml 1% , aqueous solution of the hardener of the formula

Cl

\ C

(21)

N

/

N ■

^ c- /

Cl

- N

C - NH

-O

SO ^ Na

1. Color development

2. Water

3. First fixation

4. Water

5. Silver bleaching

6.Water

7. Second fixation

8.Water

9. Dry

5 minutes 5 minutes 2 minutes 2 minutes 2 minutes 2 minutes 2 minutes 2 minutes 10 minutes

The processing solutions have the following composition:

I. Color development solution (pH = 10.7)

20th

and 1.7 ml of water are mixed together and poured onto a substrate glass plate of 13-18 cm at 40 ° C. After solidification at 10 ° C, the plate is dried in a drying cabinet with circulating air at 32 ° C

A strip cut to 4.0 • 6.5 cm is exposed to 500 lux / cm2 under a step wedge for 2 seconds and then treated at 24 ° C as follows:

4-amino-3-methyl-N-ethyl-N-ß- (methyl-sulfonamido) -ethylani-

lin; 1 Vi HîSO-e H20.10 mmol

anhydrous sodium sulfite

2.0 g

Potassium bromide

0.5 g

Potassium carbonate

40.0 g

Benzyl alcohol

10.0 g

water

1000 g

IL fixation (pH = 4.5)

Sodium thiosulfate6 H2O

80.0 g of anhydrous sodium sulfite

5.0 g

Sodium borate (borax)

6.0 g

Potassium alum

7.0 g

acetic acid

4.0 g

water

1000g

III. Silver bleaching bath (pH = 7.2)

Potassium hexacyanoferrate (III)

100.0 g

Boric acid

10.0 g

Sodium borate (borax)

5.0 g

water

1000 g

A clear, sharp yellow wedge is obtained with an absorption maximum at 445 nm and a color density of 1.22.

G