US2886436A - 5-amino-8-hydroxyquinolines as coupling components for azine dye images - Google Patents

5-amino-8-hydroxyquinolines as coupling components for azine dye images Download PDF

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US2886436A
US2886436A US641481A US64148157A US2886436A US 2886436 A US2886436 A US 2886436A US 641481 A US641481 A US 641481A US 64148157 A US64148157 A US 64148157A US 2886436 A US2886436 A US 2886436A
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amino
dye images
azine dye
acid
hydroxyquinolines
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US641481A
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Willy A Schmidt
Robert F Coles
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GAF Chemicals Corp
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General Aniline and Film Corp
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32—Colour coupling substances
    • G03C7/3244—Couplers forming azinic dyes; Specific developers therefor
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
    • C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2

Definitions

  • magenta azine dye images are of importance because of their greater brilliance and stability than the magenta quinonimine dye images obtained'in the usual fashion by coupling of a pyrazolone with the oxidation products-of a p-phenylenediamine.
  • azine dye images be produced with the conventional p-phenylenediamine developers as may be seen from a reference to US. Patents 2,536,010 and 2,543,338.
  • the color former which is used to produce the azine dyes is an aromatic phenol containing in the meta-position to the hydroxyl group, a sulfonyl amino group. After color forming development to produce the usual quinonimine dye, a ring closure is effected with elimination of the sulfonyl radical attached to the amino nitrogen atom.
  • the color formers used are aromatic amines which contain in the meta-position to the amino group, an arylamino group or a cyano-or acylamino group.
  • ring closure takes place through elimination of the substituents on the amino nitrogen atom, meta to the amino group.
  • w-l r acyl such as acetyl, propionyl, butyryl, benzoyl and the like or sulfonyl such as methyl sulfonyl, ethyl sulfonyl, phenyl sulfonyland the like
  • A is hydrogen, carboxyl or carbamino, i.e., -CONH or CONHR in which R is an alkyl radical as above or a sulfonated aromatic radical containingan aliphatic radical of at least five carbon atoms
  • B is hydrogen, alkyl as above or an aromatic radical of the benzene series as above
  • C is hydrogen, hydroxy, carboxy, alkyl as above, or an aromatic radical of the benzene series as above.
  • color formers within the ambit of the above formula are the following:
  • Compound 1 6-(p-methoxyphenylamino)-8-hydroxy-2-methy1cinchontuic aci 6-ethylamino-S-hydroxyquinoline All of the above compounds may be prepared by well known reactions. Typically, Compound 1 may be prepared as follows:
  • the other six substituted 8-hydroxyquinolines specifically listed may be prepared by reacting the selected amine with a 6-haloquinoline in an autoclave at 150200- for 4 to 10 hours in the presence of a copper catalyst.
  • n-butylamine is reacted in this way with 6-chlo1'o- 8- hydroxy-Z-phenylcinchoninic acid or p-anisidine with 6- chloro-S-hydroxy-Z-methylcinchoninic acid to yield Comat pounds 6 and 8 respectively.
  • ethylamine is reacted with 6-bromo-8-hydroxyquinoline to yield Compound 9 and methylamine reacted with 6-chloro- S-hydroxycinchoninic acid toyi eld Compound 7.
  • a conversion of the secondary amine to amides or sulfonarnides is effected by reaction of the amine with an appropriate carbonylchloride in the presence of an acid binding agent such as pyridine or triethylamine.
  • the product is then isolated by the removal of the solvent at reduced pressure and acidification of the residue after dilution with water.
  • the 4-carboxamides, as in Compound 3 are prepared by treatment of a mixture of 6-amino-2-myristoylaminotoluene-4-sulfonic acid and 6-(methylaminobenzenesulfonamide)-8-hydroxy-2-methylcinchoninic acid in pyridine solution with one-half mole of phosphorous trichloride.
  • the azine dye image is produced from the originally formed quinonimine through elimination of the elements of acyl or sulfonyl from the amino group ortho to the intermediate azomethine coupled position in the quinoline nucleus and elimination of hydrogen from the benzene, ring ortho to the primary amino group originally present in the developer molecule.
  • Such ring closure is schematically represented by the following equation:
  • a color developing solution is prepared as follows:
  • Compound 1 0.1 gram was dissolved in 5% sodium carbonate solution (5 mls.) and the solution was made up to 5 0 mls. with a portion of the aforesaid color developer solution.
  • a strip of exposed positive film is agitated in this solution for 5 to 10 minutes.
  • the film on which a green azomethine dye is orginally produced is bleached in ferricyauide and fixed in acid hypo. On treatment with the acid hypo, the green azomethine dye converts to a brilliant magenta azine dye.
  • any of the compounds listed above may be utilized for our purpose.
  • the couplers are to be employed in the emulsion, they should contain a non-difiusing group, preferably an alkyl chain of at least 1-0 carbon atoms as per Compound 3. If, on the other hand, they are to be used in the developer, they should not possess groups which render them nondifiusing in the emulsion.
  • W is selected from the class consisting of alkyl, hydroxyalkyl, carboxyalkyl, sulfoalkyl, and aryl of the benzene series
  • Y is selected from the class consisting of hydrogen, acyl and sulfonyl groups.
  • A is selected from the class consisting of hydrogen, carboxyl and carbamino groups
  • B is selected from the class consisting of hydrogen, alkyl and aryl of the benzene series
  • C is selected from the class consisting of hydrogen, hydroxy, carboxy, alkyl and aryl of the benzene series.
  • W is selected from the class consisting of alkyl, hydroxyalkyl, carboxyalkyl, sulfoalkyl and aryl of the benzene series
  • Y is selected from the class consisting of hydrogen, acyl and sulfonyl groups
  • A is selected from the class consisting of hydrogen, carboxyl and carbamino groups
  • B is selected from the class consisting of hydrogen, alkyl and aryl of the benzene series
  • C is selected from the class consisting of hydrogen, hydroxy, carboxy, alkyl and aryl of the benzene series.

Description

S-AMINO-S-HYDROXYQUINOLINES AS COUPLING COMPONENTS FOR AZINE DYE IMAGES Willy A. Schmidt, Binghamton, and Robert F. Coles,
Vestal, N .Y., assignors to General Aniline & Film Corporation, New York, N .Y., a corporation of Delaware No Drawing. Application February 21, 1957 Serial No. 641,481
5 claims. or. 96-55) enediamine class, and to a process of producing such azinedyestufi images.
It is recognized that 8-hydroxyquinoline, like any of nitcd States Patent the phenols when used as a color former for the production of dye images by color development customarily yields blue to blue-green quinonimines with the oxidation products of a p-phenylenediamine color developer. On
the other hand, the S-hydroxyquinolines are known to.
produce azine dyestufr images where the color developer is a triamine rather than a diamine, specifically a 4,6-diamino metanilic acid and, in this connection, reference may be made to U. S. Patents 2,486,440; 2,524,741; 2,579,420 and 2,524,725. These, magenta azine dye images are of importance because of their greater brilliance and stability than the magenta quinonimine dye images obtained'in the usual fashion by coupling of a pyrazolone with the oxidation products-of a p-phenylenediamine.
It has been suggested that azine dye images be produced with the conventional p-phenylenediamine developers as may be seen from a reference to US. Patents 2,536,010 and 2,543,338. In the earlier patent, however, the color former which is used to produce the azine dyes is an aromatic phenol containing in the meta-position to the hydroxyl group, a sulfonyl amino group. After color forming development to produce the usual quinonimine dye, a ring closure is effected with elimination of the sulfonyl radical attached to the amino nitrogen atom.
In the latter patent, the color formers used are aromatic amines which contain in the meta-position to the amino group, an arylamino group or a cyano-or acylamino group. Here again, after formation of the usual quinonimine, ring closure takes place through elimination of the substituents on the amino nitrogen atom, meta to the amino group.
In each case, it is evident that, on the nitrogen atom in meta-position to the'hydroxyl or amino group, there is present, a substituent group which is readily cleaved to permit ring closure to the azine.
A further method for producing azine dye images by resort to the conventional p-phenylenediamine developers is described in US. Patent 2,701,766. According to this patent, the color former is a 6-halogen-8-hydroxycinchoninic acid which, during color forming development, reacts with the oxidation products of the p-phenylenediamine to produce a quinonimine dye image. The quinonimine dye image then reacts with an additional molecule of the developer oxidation products with elimination of the halogen atom in 6-position to effect ring closure to an azine dye. In this procedure, it is recommended that an alkaline bath be employed to promote elimination of the halogen atom in the 6-position and ring closure to the azine.
2,886,436 Patented May 12, 1959 We have now discovered that it is possible to produce magenta azine dye images directly and without the use of any auxiliary baths by color development with a pphenylenediamine developer providing that there is employed, as the color former, a 6-amino-8-hydroxyquinoline in which the amino group is secondary or tertiary and contains replaceable hydrogen or an acyl or sulfonyl group. Photographic emulsions, and p-phenylenediamine developers containing such color formers, and the processing of exposed silver halide emulsions with p-phenylenediamine developers in the presence of such color formers to produce magenta azine dye images constitute the purposes and objects of our invention.
The color formers contemplated for use herein are typified by the following structure:
w-l r acyl such as acetyl, propionyl, butyryl, benzoyl and the like or sulfonyl such as methyl sulfonyl, ethyl sulfonyl, phenyl sulfonyland the like, A is hydrogen, carboxyl or carbamino, i.e., -CONH or CONHR in which R is an alkyl radical as above or a sulfonated aromatic radical containingan aliphatic radical of at least five carbon atoms, B is hydrogen, alkyl as above or an aromatic radical of the benzene series as above and C is hydrogen, hydroxy, carboxy, alkyl as above, or an aromatic radical of the benzene series as above.
Examples of color formers within the ambit of the above formula are the following:
i Refrain-N N/ in;
N,6- 8-hydroxy-2-methyl-4-carboxyqulnolinyl) acetanilide H 0 H I I ll CNv is 21 O CH:
Liq- Q a...
3 tetra decanoylamido 4 methyl-5- [8-hydroxy-6-(N-methylbenzenesulfonamido) cinchoniuoyl] amidobenzene sulfonic acid G-phenylamino-8-hydroxy-2 ,3-dimethylcinchoninlc acid I H O C gH -N i N OH 6- (B-hy-droxyethylamino)-8-hydroxyqui.uo1ine CO H NW (SE 6-butylamino-8-hydroxy-2-pheny1cinchoninic acid H C Hrl l i N H 6-methylamino-8-hydroxycinchon1nic acid H t'r CHgO- N CH;
6-(p-methoxyphenylamino)-8-hydroxy-2-methy1cinchontuic aci 6-ethylamino-S-hydroxyquinoline All of the above compounds may be prepared by well known reactions. Typically, Compound 1 may be prepared as follows:
A solution of 2-phenyl-6-chloro-8-hydroxycinchoninic acid (15 gms., 0.05 mole) in 50 mls. of water containing sodium hydroxide (2 guts, 0.05 mole) was treated with ethanolamine (3.5 mls., 0.058 mole) calcium carbonate (2.5 gms., 0.05 mole) and a trace of copper sulfate and copper bronze powder. The mixture was heated at 175 in an autoclave for 10 hours. After the reaction period, the insoluble material was removed by filtration and the filtrate acidified with hydrochloric acid. The brown solid was collected and washed with water. The solid was extracted twice with 100 ml. portions of hot methanol and the residue discarded. After dilution of the extract with water and heating to coagulate the solid, the product was collected. The solid was finally dissolved in dilute bicarbonate solution and re-isolated by acidification with hydrochloric acid.
The other six substituted 8-hydroxyquinolines specifically listed may be prepared by reacting the selected amine with a 6-haloquinoline in an autoclave at 150200- for 4 to 10 hours in the presence of a copper catalyst. Thus, n-butylamine is reacted in this way with 6-chlo1'o- 8- hydroxy-Z-phenylcinchoninic acid or p-anisidine with 6- chloro-S-hydroxy-Z-methylcinchoninic acid to yield Comat pounds 6 and 8 respectively. In a similar manner, ethylamine is reacted with 6-bromo-8-hydroxyquinoline to yield Compound 9 and methylamine reacted with 6-chloro- S-hydroxycinchoninic acid toyi eld Compound 7.
A conversion of the secondary amine to amides or sulfonarnides is effected by reaction of the amine with an appropriate carbonylchloride in the presence of an acid binding agent such as pyridine or triethylamine. The product is then isolated by the removal of the solvent at reduced pressure and acidification of the residue after dilution with water.
The 4-carboxamides, as in Compound 3 are prepared by treatment of a mixture of 6-amino-2-myristoylaminotoluene-4-sulfonic acid and 6-(methylaminobenzenesulfonamide)-8-hydroxy-2-methylcinchoninic acid in pyridine solution with one-half mole of phosphorous trichloride.
In our procedure, the azine dye image is produced from the originally formed quinonimine through elimination of the elements of acyl or sulfonyl from the amino group ortho to the intermediate azomethine coupled position in the quinoline nucleus and elimination of hydrogen from the benzene, ring ortho to the primary amino group originally present in the developer molecule. Such ring closure is schematically represented by the following equation:
i f'N Color former Developer Example I A color developing solution is prepared as follows:
Gms.
p-Aminodiethylaniline 2 Sodium carbonate (anhydrous) 50 Sodium sulfite (anhydrous) 2 Potassium borate .2
Water to' make 1 liter.
0.1 gram of Compound 1 was dissolved in 5% sodium carbonate solution (5 mls.) and the solution was made up to 5 0 mls. with a portion of the aforesaid color developer solution.
A strip of exposed positive film is agitated in this solution for 5 to 10 minutes. The film on which a green azomethine dye is orginally produced is bleached in ferricyauide and fixed in acid hypo. On treatment with the acid hypo, the green azomethine dye converts to a brilliant magenta azine dye.
Example [1 tioned in Examples I and II, any of the compounds listed above may be utilized for our purpose. Where the couplers are to be employed in the emulsion, they should contain a non-difiusing group, preferably an alkyl chain of at least 1-0 carbon atoms as per Compound 3. If, on the other hand, they are to be used in the developer, they should not possess groups which render them nondifiusing in the emulsion.
It is equally evident that, in lieu of the p-aminodiethylaniline of Example I, other p-phenylenediamines may be used as, for example, 4-diethylaminoaniline, 4 :dipropylaminoaniline, 4 (N-methyl-N-hydroxyethylamino)aniline, 4-(N-ethyl-N-hydroxyethylamino)aniline, and 4- (N,N'-dihydroxyethylamino) aniline.
We, therefore, do not intend to be limited in the patent granted except as necessitated by the appended claims.
We claim:
1. Process of producing magenta azine dye images which comprises exposing to light a light sensitive silver halide emulsion and developing the same with a p-phenylenediamine developer in the presence of a color former of the following formula:
I W-N B wherein W is selected from the class consisting of alkyl, hydroxyalkyl, carboxyalkyl, sulfoalkyl, and aryl of the benzene series, Y is selected from the class consisting of hydrogen, acyl and sulfonyl groups. A is selected from the class consisting of hydrogen, carboxyl and carbamino groups, B is selected from the class consisting of hydrogen, alkyl and aryl of the benzene series, and C is selected from the class consisting of hydrogen, hydroxy, carboxy, alkyl and aryl of the benzene series.
2. The process as defined in claim 1 wherein the color former is 2-phenyl-6-(fi-hydroxyethylamino)-8-hydroxycinchoninic acid.
3. A light sensitive silver halide emulsion containing as a color former for magenta, the compound of the following formula:
Y A w-r r B wherein W is selected from the class consisting of alkyl, hydroxyalkyl, carboxyalkyl, sulfoalkyl and aryl of the benzene series, Y is selected from the class consisting of hydrogen, acyl and sulfonyl groups, A is selected from the class consisting of hydrogen, carboxyl and carbamino groups, B is selected from the class consisting of hydrogen, alkyl and aryl of the benzene series, and C is selected from the class consisting of hydrogen, hydroxy, carboxy, alkyl and aryl of the benzene series.
4. The light sensitive silver halide emulsion as defined in claim 3 wherein the color former contains a long chain alkyl radical rendering it non-diffusing in the emulsron.
5. A light sensitive silver halide emulsion containing as a color former for magenta, a compound of the following constitution:
CH3 0 1'1 I 0 Hi- Ni '-O1 H17 References Cited in the file of this patent UNITED STATES PATENTS 2,701,766 Hensley Feb. 8, 1955 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No, 2,886,436 May 12, 1959 Willy A, Schmidt et al,
It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.
Column 2, line 36,, for "CONHB" read -=-CONHR column 5, line 13, for 'firing" read me fixing Signed and sealed this 31st day of May 1960.,
(SEAL) Attest: I
KARL ROBERT C. WATSON Attesting Ofiicer 7 Commissioner of Patents

Claims (1)

1. PROCESS OF PRODUCING MAGENTA AZINE DYE IMAGES WHICH COMPRISES EXPOSING TO LIGHT A LIGHT SENSITIVE SILVER HALIDE EMULSION AND DEVELOPING THE SAME WITH A P-PHENYLENEDIAMINE DEVELOPER IN THE PRESENCE OF A COLOR FORMER OF THE FOLLOWING FORMULA:
US641481A 1957-02-21 1957-02-21 5-amino-8-hydroxyquinolines as coupling components for azine dye images Expired - Lifetime US2886436A (en)

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GB5146/58A GB837360A (en) 1957-02-21 1958-02-17 6-amino-8-hydroxyquinolines as coupling components for azine dye images

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3970454A (en) * 1974-01-10 1976-07-20 Eastman Kodak Company Photographic developing agents
US4327173A (en) * 1980-01-23 1982-04-27 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4814454A (en) * 1985-10-28 1989-03-21 E. R. Squibb & Sons, Inc. Quinoline compounds and compositions thereof
US4847381A (en) * 1987-08-31 1989-07-11 American Cyanamid Company 2-Phenyl-4-quinoline carboxylic acids
US5573892A (en) * 1994-11-04 1996-11-12 Agfa-Gevaert Ag Use of Yellow couplers of the indolo [3,2-B] guinoline type in a colo ur photographic development process

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2701766A (en) * 1952-06-14 1955-02-08 Gen Aniline & Film Corp Developers for and method of producing phenazonium dyestuff images with p-dialkylaminoaniline developing agents

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2701766A (en) * 1952-06-14 1955-02-08 Gen Aniline & Film Corp Developers for and method of producing phenazonium dyestuff images with p-dialkylaminoaniline developing agents

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3970454A (en) * 1974-01-10 1976-07-20 Eastman Kodak Company Photographic developing agents
US4327173A (en) * 1980-01-23 1982-04-27 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4814454A (en) * 1985-10-28 1989-03-21 E. R. Squibb & Sons, Inc. Quinoline compounds and compositions thereof
US4847381A (en) * 1987-08-31 1989-07-11 American Cyanamid Company 2-Phenyl-4-quinoline carboxylic acids
US5573892A (en) * 1994-11-04 1996-11-12 Agfa-Gevaert Ag Use of Yellow couplers of the indolo [3,2-B] guinoline type in a colo ur photographic development process

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GB837360A (en) 1960-06-15

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