US2591642A - Nondiffusing color formers comprising aryl j-acids in which the aryl radical is provided with a nondiffusing group - Google Patents

Nondiffusing color formers comprising aryl j-acids in which the aryl radical is provided with a nondiffusing group Download PDF

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Publication number
US2591642A
US2591642A US137886A US13788650A US2591642A US 2591642 A US2591642 A US 2591642A US 137886 A US137886 A US 137886A US 13788650 A US13788650 A US 13788650A US 2591642 A US2591642 A US 2591642A
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United States
Prior art keywords
acid
aryl
mixture
nondiffusing
acids
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US137886A
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English (en)
Inventor
Tulagin Vsevolod
Robert F Coles
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GAF Chemicals Corp
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General Aniline and Film Corp
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Priority to BE500494D priority Critical patent/BE500494A/xx
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US137886A priority patent/US2591642A/en
Priority to GB84/51A priority patent/GB691989A/en
Priority to DEG4984A priority patent/DE874248C/de
Application granted granted Critical
Publication of US2591642A publication Critical patent/US2591642A/en
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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

Definitions

  • the present invention relates to non-diffusing color formers of theqaryl-J-acid .typein which the non-diii'using group appears in the aryl radical joined to the nitrogen atom in the 6- position of the J-acid,-and the use of such color formers in the preparation of cyan azine dye
  • the dye which is produced when using this color former has very desirable spectral char:
  • A is a radical of aromatic character and of the benzene, naphthalene, pyridine or quinoline series
  • X is C'O--, --OCH2CO, -CH2CO, or --NHCH2CO
  • Y is an aliphatic atoms or an aromatic radical containing an aliphatic chain of at least 10 carbon atoms
  • R is hydrogen or a salt forming group, such as sodium, potassium, and the like, and R is an aliphatic hydrocarbon group having less than -1- carbon atoms.
  • the long chain amidesprepared as above are. non-diffusing color formers.
  • a such, however,- theX cannot be used for-the preparation; of multilayer,- colonfilm because they are very easily'oxia dized; and lead to the production of an. overall brown. stain during the normal processing. of such. multilayer film.
  • the formation of the.acylami-no' derivatives can be readily effected by treating the amides with the desired acid anhydride, i. e., acetic, propionic or butyric,'while heating-the reaction mixture.
  • the 'colorformers of the present invention whendispersed in silver halide emulsion may be converted into; cyan azine dye; images; by develf omentwith .t-hede eopcrs of; U. s. Patent No.”
  • the dev l p rs; employ d; in suchp ocess n contain not only the desired 2,4-diamino aniline and an alkali such'as sodium carbonate, sodium hydroxide or thelike, but preferably in addition theusual adjuncts suchas an'alkali metal.
  • bromide i. e., potassium bromide
  • an alkali metal sulfite such as'sodium sulfite.
  • the mixture was refluxed for 1% hours.
  • the sodium salt of J -acid (40 g.) was added, and .the mixture was refluxedfor 2 hours.
  • The. hotmixture was filtered and the solid tar. obtained was.
  • EXAMPLE 2 7 -carbo:cy-2 -n.aphthy l J acid
  • the "7'-carboxy-2'-naphthyl J-acid was obtained by the same procedure as that described for the 6'-carboxy-2'-naphthyl J-acid.
  • ExAMPLn 3 8-carbo.ry naphthoxy 2 '-naphthyl .l-aczd Into a, 1-liter 3-neck flask, equipped, with a stirrer and a reflux condenser, were placed 22 g. of 7-amino-1-naphthoxy aceticacidand. 15 0. cc. of warm water. The. mixture was stirredand treated with concentrated ammonium hydroxide.
  • EXAMPLE 4-carbo:cy phenyl J-acid Into a 3- liter 3-neck flask, equipped with a stirrer and a reflux condenser was placed a solution of 770 g. J-acid paste (54%) in 1000 cc. of water containing 95 g. of sodium hydroxide. The mixture was heated to boiling and p-amino benzoic acid (210 g.) and sodium meta bisulfite (500 g.) were added and the mixture was refiuxed for 5 hours. The reaction mixture was diluted with 1000 cc. of water and acidified with concentrated hydrochloric acid to a pH of 1-2. The resulting suspension was filtered. The solid was washed repeatedly with water.
  • the material was suspended in 3 liters of hot water and potassium acetate was added until a solution had taken place. Saturated potassium chloride solution (500 cc.) was added and the solution was cooled. The crystalline solid which had separated was collected by filtration and washed with potassium chloride solution. The material was further purified by repeated crystallization from 10% potassium chloride solution. A good test for the purity of the material consists of dissolving a small portion in water and acidifying with hydrochloric acid. If the substance is pure, no precipitate will be obtained while the mixture is hot; the whole mixture will set into a jelly upon cooling.
  • the 4-carboxy phenyl J -acid is best converted to the pyridine salt. This may be accomplished in the following manner:
  • the solid obtained above is dissolved in 2 liters of hot water containing pyridine (200 60.). The solution is strongly acidified with concentrated hydrochloric acid and allowed to cool. The yellow crystalline solid so obtained is collected by filtration, washed with water and dried.-
  • EXAMPLE 6 4-carborymethylphen'yl-J-acid Into a 1-liter E-necked flask, equipped with an agitator and a reflux condenser, were placed a solution of 10 g. of sodium hydroxide in 200 cc. of water, 66 g. of J-acid and 38 g. of p-amino phenyl acetic acid. The mixture was stirred until a solution was obtained and then 100 g. ofsodi- 8 collected by filtration and dissolved in 500 cc. of hot water. Concentrated hydrochloric acid (50 cc.) was added and the suspension so obtained was cooled to 30-40 C. The product which separated at this point was collected by filtration, washed with dilute hydrochloric acid and dried.
  • EXAMPLE 7 3'-carbo:cy methyl amino phenyl J-acid
  • the 3'-earboxy methyl amino phenyl J acid may be prepared by the methods given above starting with 3-aminophenyl glycine and J -acld.
  • EXAMPLE 8 Z-methyl-el-carbozcy-fi-quinoline J-acid Into a 1-liter 3-necked flask, equipped with an agitator and; a reflux condenser were placed 200 cc. of water, 4 g. of sodium hydroxide, 20 g. of 2-methyl-6-amino cinchoninic acid, 39 g. of J- acid and 50 g. of sodium meta bisulfite. The mixture was refluxed for one hour and treated with an additional 13 g. of J -acid. The mixture was further refluxed for an additional three hours. The resulting suspension was cooled and filtered. The solid was collected by filtration and triturated with 3 N hydrochloric acid.
  • the insoluble material was collected by filtration and thoroughly washed with water.
  • the solid was dissolved in hot dilute sodium hydroxide solution; the solution was acidified with acetic acid and cooled.
  • the crystalline solid so obtained was dissolved in hot water,- and the solution was strongly acidified with concentrated hydrochloric acid.
  • the dark red solid thus obtained was collooted by filtration, washed with water, and dried. 7
  • EXAMPLE 9 4-carboxy-6-pyridino J-acz'd The procedure is the same as in Example 8 excepting that the 2-methyl-fi-amino-cinchoninic acid is replaced by an equivalent amount of .6- amino nicotinic acid.
  • the solvents are removed at reduced pressure, the residue dissolved in 300' ml. of hot water, filtered, and the filtrate acidified strongly with hydrochloric acid.
  • the solid is collected and dissolved in 500 ml. of hot water, filtered through a celite pad and the filtrate treated with ml. of concentrated hydrochloric acid (or until precipitation is complete).
  • the mixture is heated to coagulate the solid and the solid collected by filtration.
  • the solid is extracted with 500 ml. of boiling glacial acetic acid. 20 cc. of acetic anhydride are added to the extract and the mixture is refluxed for /2 hour. a
  • the mixture is fil- 'tered'hot, washed with petroleum etherkand thol-3-sulfonic acid.
  • the product is '6-iN-propionyli-(3 stearoylamino sulfo otolyl carbamylmethyD- anilinol -l-naphth'ol-3-sul'fonicacid.
  • The-product may be purified from crystallization from 50% mixture of glacial acetic-acid and absolute alcohol.
  • EXAMPLE'14 v 'In a 500 ml. triple-necked flask equipped with a'mechanical stirrer, droppingfunnel and reflux condensencarrying a water'separatorand heated on ametal bath is placed.
  • the mixture is dried in a manner similar to the above example.
  • the product is 6-[N-acetyl-3-(Z-octadecylamino sulfophenylcarbamyl)aniline] -"1'-.naphthol-"3sulfonic acid.
  • drochloride is removed by filtration andlthephosph'azo -solution "(the.'filtrate) so obtained i's usedl withoutfurther purification.
  • the placephazo solution prepared according-to the above 00.) is added and the mixture is kept at l25 for' 20'hours.
  • Acetic acid (8 cc.) is add'ed and the mixture is refluxed for hour.
  • ik'soluglacial-acetic acid is added and'themixture is refluxed for hour.
  • Aceticanhydride (20-cc9' is added-and the mixture is-refluxed "for hour.
  • This substance is a non-diffusing cyancolor former of the-probable constitution:
  • any of the color formers referred to above may be dispersed in silver halide emulsions and employed for the production of azine dye images.
  • A is a radical of aromatic character se- 12 lected from the class consisting of those of the benzene, naphthalene, pyridine and quinoline series
  • X is a carbonyl containing group selected from the class consisting of those of the following formulae: --CO-, OCH2CO, CH2CO, and --NHCH2CO-
  • Y is a radical selected from the class consisting of those of aliphatic radicals containing a chain of at least 10 carbon atoms and aromatic radicals containing an aliphatic chain of at least 10 carbonatoms
  • M is selected from the class consisting of hydrogen and salt forming groups
  • R is an aliphatic hydrocarbon group having less than 4 carbon atoms.
  • A is a radical of aromatic character selected from the class consisting of those of the benzene, naphthalene, pyridine and quinoline se-' ries
  • X is a carbonyl containing group selected from the class consisting of those of the following formulae: CO-,---OCH2CO, -CH2CO, and -NHCH2CO
  • Y. is a radical selected from the class consisting of those of aliphatic radicals containing a chain of at least 10 carbon atoms and aromatic radicals containing an aliphatic chain of at least 10 carbon atoms
  • M is selected from the class consisting of hydrogen and salt forming groups.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Pyridine Compounds (AREA)
US137886A 1950-01-10 1950-01-10 Nondiffusing color formers comprising aryl j-acids in which the aryl radical is provided with a nondiffusing group Expired - Lifetime US2591642A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE500494D BE500494A (en)) 1950-01-10
US137886A US2591642A (en) 1950-01-10 1950-01-10 Nondiffusing color formers comprising aryl j-acids in which the aryl radical is provided with a nondiffusing group
GB84/51A GB691989A (en) 1950-01-10 1951-01-01 Photographic non-diffusing color formers
DEG4984A DE874248C (de) 1950-01-10 1951-01-10 Verfahren zur Herstellung von nicht diffundierenden Farbbildnern der Aryl-J-Saeure

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3099559A (en) * 1959-08-31 1963-07-30 Gen Aniline & Film Corp Silver-free color reproduction process and composition therefor

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1273137B (de) * 1955-04-12 1968-07-18 Arthur J Schmitt Foundation Ch Verwendung einer UEberzugsmasse als Formsand-Bindemittel
US2871120A (en) * 1955-11-18 1959-01-27 Gen Aniline & Film Corp Azine cyan color formers

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2186849A (en) * 1935-08-07 1940-01-09 Agfa Ansco Corp Manufacture of photographic silver halide emulsions
US2480815A (en) * 1948-05-06 1949-08-30 Gen Aniline & Film Corp 2-naphthyl j-acid and the urethanes thereof as color formers

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2186849A (en) * 1935-08-07 1940-01-09 Agfa Ansco Corp Manufacture of photographic silver halide emulsions
US2480815A (en) * 1948-05-06 1949-08-30 Gen Aniline & Film Corp 2-naphthyl j-acid and the urethanes thereof as color formers

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3099559A (en) * 1959-08-31 1963-07-30 Gen Aniline & Film Corp Silver-free color reproduction process and composition therefor

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GB691989A (en) 1953-05-27
DE874248C (de) 1953-04-23

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