# US 4,394,440 A · Yellow-dye-forming photographic developing composition

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 4,394,440 A
- Document ID: US4394440A
- Status: Granted
- Kind: A
- Application number: 06/341,712
- Filed: 1982-01-22
- Granted: 1983-07-19
- Earliest claimed: 1982-01-22
- Assignees: Eastman Kodak Company
- Inventors: Carl R. Cappel
- Web page: https://patentgrep.com/patent/US4394440A

## CPC

- G03C 7/413: Developers
- G03C: PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES (for photomechanical purposes G03F); PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY (photographic processes characterised by the use or manipulation of apparatus classifiable per se in subclass G03B, see G03B; photomechanical production of textured or patterned surfaces G03F; electrophotography, magnetography G03G)

## Abstract

A yellow-dye-forming photographic developing composition having improved stability comprises a haloacetanilide coupler, such as alpha-pivalyl-alpha-(4-carboxyphenoxy)-2,4-dichloroacetanilide, an N-alkyl-N-alkoxyalkyl-p-phenylenediamine developing agent, such as 4-amino-N-ethyl-N-(2-methoxyethyl)-m-toluidine di-p-toluene sulfonate, and a 4,4-disubstituted-1-aryl-3-pyrazolidinone, such as 4,4-dimethyl-1-phenyl-3-pyrazolidinone.

## Claims

### Claim 1

A yellow-dye-forming photographic developing composition comprising
(1) a haloacetanilide coupler of the formula ##STR8## wherein R is a branched alkyl group of 3 to 6 carbon atoms, X is Cl or Br, Y is X, hydrogen or alkyl of 1 to 8 carbon atoms, and A and B differ and are either H or COOM where M is a photographically inactive cation or a methyl or ethyl group;
(2) an N-alkyl-N-alkoxyalkyl-p-phenylene-diamine develoing agent of the formula ##STR9## wherein n is an integer having a value of from 2 to 4, R.sup.1 is alkyl of from 1 to 4 carbon atoms, and R.sup.2 is alkyl of from 1 to 4 carbon atoms or alkoxy of from 1 to 4 carbon atoms;
and (3) a 4,4-disubstituted-1-aryl-3-pyrazolidinone balancing developing agent of the formula ##STR10## wherein R.sup.3 and R.sup.4 are the same or different and each is alkyl of 1 to 6 carbon atoms or hydroxyalkyl of 1 to 6 carbon atoms, and R.sup.5 is hydrogen, halogen, alkyl of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms.

### Claim 2

A yellow-dye-forming photographic developing composition comprising 4-amino-N-ethyl-N-(2-methoxyethyl)-m-toluidine di-p-toluene sulfonate, alpha-pivalyl-alpha-(4-carboxyphenoxy)-2,4-dichloroacetanilide, and 4,4-dimethyl-1-phenyl-3-pyrazolidinone.

### Claim 3

A yellow-dye-forming photographic developing composition comprising 4-amino-N-ethyl-N-(2-methoxyethyl)-m-toluidine di-p-toluene sulfonate, alpha-pivalyl-alpha-(4-carboxyphenoxy)-2,4-dichloroacetanilide, and 4-hydroxymethyl-4-methyl-1-phenyl-3-pyrazolidinone.

### Claim 4

An aqueous alkaline yellow-dye-forming photographic developing solution comprising from about 1 to about 4 grams per liter of a haloacetanilide coupler of the formula ##STR11## wherein R is a branched alkyl group of 3 to 6 carbon atoms, X is Cl or Br, Y is X, hydrogen or alkyl of 1 to 8 carbon atoms, and A and B differ and are either H or COOM where M is a photographically inactive cation or a methyl or ethyl group; from about 1 to about 4 grams per liter of an N-alkyl-N-alkoxyalkyl-p-phenylenediamine developing agent of the formula ##STR12## wherein n is an integer having a value of from 2 to 4, R.sup.1 is alkyl of from 1 to 4, R.sup.1 is alkyl of from 1 to 4 carbon atoms, and R.sup.2 is alkyl of from 1 to 4 carbon atoms or alkoxy of from 1 to 4 carbon atoms; and from about 0.2 to about 0.8 grams per liter of a 4,4-disubstituted-1-aryl-3-pyrazolidinone balancing developing agent of the formula ##STR13## wherein R.sup.3 and R.sup.4 are the same or different and each is alkyl of 1 to 6 carbon atoms or hydroxyalkyl of 1 to 6 carbon atoms, and R.sup.5 is hydrogen, halogen, alkyl of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms.

### Claim 5 (depends on 4)

A developing solution as claimed in claim 4 wherein said haloacetanilide coupler is alpha-pivalyl-alpha-(4-carboxyphenoxy)-2,4-dichloroacetanilide, said N-alkyl-N-alkoxyalkyl-p-phenylenediamine developing agent is 4-amino-N-ethyl-N-(2-methoxyethyl)-m-toluidine di-p-toluene sulfonate, and said 4,4-disubstituted-1-aryl-3-pyrazolidinone balancing developing agent is 4,4-dimethyl-1-phenyl-3-pyrazolidinone or 4-hydroxymethyl-4-methyl-1-phenyl-3-pyrazolidinone.

### Claim 6

In a method of reversal color processing of a photographic element in which said element is developed in a yellow-dye-forming photographic developing solution, the improvement wherein said solution comprises
(1) a haloacetanilide coupler of the formula ##STR14## wherein R is a branched alkyl group of 3 to 6 carbon atoms, X is Cl or Br, Y is X, hydrogen or alkyl of 1 to 8 carbon atoms, and A and B differ and are either H or COOM where M is a photographically inactive cation or a methyl or ethyl group;
(2) an N-alkyl-N-alkoxyalkyl-p-phenylenediamine developing agent of the formula ##STR15## wherein n is an integer having a value of from 2 to 4, R.sup.1 is alkyl of from 1 to 4 carbon atoms, and R.sup.2 is alkyl of from 1 to 4 carbon atoms or alkoxy of from 1 to 4 carbon atoms;
and (3) a 4,4-disubstituted-1-aryl-3-pyrazolidinone balancing developing agent of the formula ##STR16## wherein R.sup.3 and R.sup.4 are the same or different and each is alkyl of 1 to 6 carbon atoms or hydroxyalkyl of 1 to 6 carbon atoms, and R.sup.5 is hydrogen, halogen, alkyl of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms.

### Claim 7 (depends on 6)

An improved method as claimed in claim 6 wherein said haloacetanilide coupler is alpha-pivalyl-alpha-(4-carboxyphenoxy)-2,4-dichloroacetanilide, said N-alkyl-N-alkoxyalkyl-p-phenylenediamine developing agent is 4-amino-N-ethyl-N-(2-methoxyethyl)-m-toluidine di-p-toluene sulfonate, and said 4,4-disubstituted-1-aryl-3-pyrazolidinone balancing developing agent is 4,4-dimethyl-1-phenyl-3-pyrazolidinone or 4-hydroxymethyl-4-methyl-1-phenyl-3-pyrazolidinone.