US2525502A - Production of phenazonium dyestuff images - Google Patents

Production of phenazonium dyestuff images Download PDF

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Publication number
US2525502A
US2525502A US793534A US79353447A US2525502A US 2525502 A US2525502 A US 2525502A US 793534 A US793534 A US 793534A US 79353447 A US79353447 A US 79353447A US 2525502 A US2525502 A US 2525502A
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color
phenazonium
benzoquinoline
hydroxy
images
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Expired - Lifetime
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US793534A
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Tulagin Vsevolod
Willy A Schmidt
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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

Definitions

  • the present invention relates to the production of blue-green or cyan phenazonium dyestuff images by color development of an exposed silver halide emulsion with an ortho-phenylenediamine type developer in the presence of a 7.8- benzoquinoline as the color former.
  • cyan ,orbluegreen phenazonium dyestufi images are obtained by color developing an exposed silver halide emulsion with an ortho-phenylenediamine type developer in the presence of a benzoquinoline containing in the hetero ring thereof an auxolchromic group such as hydroxyl, amino, ,or substituted amino.
  • R is an auxochromic group, such as 2-metl1yl-4.5-dihydroxy-7.8-benzoquinollne H OWN Q H 2.4-dihydroxy-4-methy1-7.8-benzoquino1iue HiC V 2-methy1-4,4' -dihydroxy-5.6-benzoquino1ine 2-methy1-4,5'-dihydroxy-S.G-benzoquinoline i NO-AsOaH:
  • Compounds 6, 7, 8, 11 and 12 can be prepared by reacting compound 2 with a mixture of ethyl bromide and sodium hydroxide, treating the compound obtained with phosphorus oxychloride, followed by reaction with a mixture of hydrobromic and acetic acids to obtain -2-'methy1-4-ch1oro-4 hydro'xy-V.8 benzoquino1ine. Upon heating of the latter compound in the presence of a trace of hydrochloric acid with p-amin'ophenylarsonic a in r sp ct v y, the desired compounds are obtained.
  • Compounds 9 and 10 can be obtained by reacting Z-methyll-chloro-'-hydroxy-7.8- benzoquinoline with p-phenylenediamine and monotetradecyl-p-phenylene diamine and then reacting the resultant compounds with a mixture of chloroacetyl chloride and acetic acid and finally heating with an aqueous solution of sodium sulfite.
  • the color formers are employed either in the emulsion or in the developer. However, where they contain a group preventing diffusion, they are preferably used in the emulsion. Examples of compounds falling'within such category are compounds 8 and 11 above.
  • the color developers which are employed are, as stated, of the ortho-phenylenediamine type, a number of examples of which are referred to in the aforesaid Schmidt and Tulagin application. Suitable developers of this class are:
  • the invention may be efiectuated so as to use the color developing method for producing 001- ored negatives, colored positives, or reversed images.
  • These general methods are conventional in the art, being dependent for their efficacy upon the point at which color development takes place.
  • Example 1 To 1 kilo of a silver bromide iodide emulsion is added .7 gram of Z-methyll-(4-N-tetradecylsulfoacetamido-aniline)-4'hydroxy-7.8 benzoquinoline, and the mixture is coated on a suitable support. The resulting film is exposed and developed in a black and white developer. The film is thoroughly washed and the residual silver halide re-exposed and developed in a developer of the following composition:
  • Example 2 A silver bromide emulsion is exposed and color developed in a developer of the following constitution:
  • Color of Formed Coupler Dye 2-methyl-4.4-dihydroxy7.8-benzoquinoline 2. i-dihydroxy-4-methyl-7.S-benzoquinoline, 2-methyl-4(4"-arsonoanilino)-4-hydroxy 7.8-benzoquinoline. 2-methy1-4 (4-si 1lloanilino) 4-hydroxy-7.8-benzoquinollne. 2-methyl-4 (4@eulfcacetamidoaniline) -4-hydroxy- 7.8-benzoquinoline. 7
  • R is an auxochromic group selected from the class consisting of hydroxy and amino groups
  • R1 is lower alkyl
  • the OH indicated in the formula is in the B-position of the designated benzo ring
  • R and R1 are both in the heterocyclic ring.
  • R is an auXochromic group selected from the class consisting of hydroxy and. amino groups
  • R1 is lower alkyl
  • the OH indicated in the formula is in the [3-position of the designated benzo ring
  • R and R1 are both in the heterocyclic ring, said compound being free from groups rendering said compound non-diffusing in photographic emulsions.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Quinoline Compounds (AREA)

Description

Patented Oct. 10, 1,950
UNITED STATES PATENT OFFICE PRODUCTION OF PHENAZONIUM DYESTUFF IMAGES N Drawing.
7 Claims.
The present invention relates to the production of blue-green or cyan phenazonium dyestuff images by color development of an exposed silver halide emulsion with an ortho-phenylenediamine type developer in the presence of a 7.8- benzoquinoline as the color former.
Schmidt and Tulagin copending application Serial Number $10,382, filed January 10, 1946, now Patent No. 2,486,440, describes the production of phenazonium dyestuff images by color developing an exposed silver halide-emulsion with a color developer comprising an ortho-phenylenediamine type developer the presence of various color formers. Among the color formers mentioned are those'cont'aining a phenolic hydroxyl group which couples in para position to such group. It has been observed that with the color formers mentioned in said copending application, the most common color of the dyestuff images obtained is either red or that shade of red known in the photographic art as magenta. As a matter of fact, it may be said that these are the only shades which are obtainable from phenols or naphthols when the coupling reaction takes place para to the phenolic hydroxyl group. This limitation on the shades -of the dyestuffs produced according to the method of said application imposes a restriction on its'use in threecolor photography. v
It has now been discovered that cyan ,orbluegreen phenazonium dyestufi images are obtained by color developing an exposed silver halide emulsion with an ortho-phenylenediamine type developer in the presence of a benzoquinoline containing in the hetero ring thereof an auxolchromic group such as hydroxyl, amino, ,or substituted amino. I
The production of .phenazonium ,dyestuff images by the utilization of such color formers and silver halide-emulsions and color developers containing such color formersconstitute the purposes and objects-of the present invention.
The benzoquinolines contemplated for .employment herein may be represented by the following structural formula? 7 Application December 23, 1947, Serial No. 793,534
5,6'-benzoquinolines or benzo[i]quinolines 7,8-benzoquinolines or benzo[h]quinolines wherein R is an auxochromic group, such as 2-metl1yl-4.5-dihydroxy-7.8-benzoquinollne H OWN Q H 2.4-dihydroxy-4-methy1-7.8-benzoquino1iue HiC V 2-methy1-4,4' -dihydroxy-5.6-benzoquino1ine 2-methy1-4,5'-dihydroxy-S.G-benzoquinoline i NO-AsOaH:
2-methyl-4(4"-arsonoani1ino)-4'-hydroxy-7.8- Y
benzoquinoline 2-methy1-4-amino4'-hydroxy-7.8-benzoquinoline 2-methy1-4 (4 '-su1f ani1ino -4'-hydroxy-7.d-henz qui oliue Nix-OM10 0 ems 03H 0 H3 N Q H 2-methyl-4 (4' -sulfoacetamidoani1ine) -4-hydroxy-7.8- benzoquinoline N-ooomsosn 2-methy1-4 (4"-N-tetradecyl-sulfoacetamidoaniline) 4'- hydroxy-7.8-benzoquino1ine Hac- 12. 1TIH- CnHas 2-methyl-4-1aury1amino-4 hydroxy-7.S-benzoquinoline The benzoquinolines employed as color formers in this invention can be prepared by the following general methods: Thus, compounds '1, 2, 4 and 5 can be prepared by reacting the appropriate aminonaphthol with ethyl acetoacetate in the presence of a trace of hydrochloric acid and then heating the intermediate reactionproduct in mineral o'i1,.to produce the benzoquinoline. Compound 3 is obtainedcby' reacting l-amino-7a naphthol with diketene and then heating at C. the reaction product in sulfuric acid. Compounds 6, 7, 8, 11 and 12 can be prepared by reacting compound 2 with a mixture of ethyl bromide and sodium hydroxide, treating the compound obtained with phosphorus oxychloride, followed by reaction with a mixture of hydrobromic and acetic acids to obtain -2-'methy1-4-ch1oro-4 hydro'xy-V.8 benzoquino1ine. Upon heating of the latter compound in the presence of a trace of hydrochloric acid with p-amin'ophenylarsonic a in r sp ct v y, the desired compounds are obtained. Compounds 9 and 10 can be obtained by reacting Z-methyll-chloro-'-hydroxy-7.8- benzoquinoline with p-phenylenediamine and monotetradecyl-p-phenylene diamine and then reacting the resultant compounds with a mixture of chloroacetyl chloride and acetic acid and finally heating with an aqueous solution of sodium sulfite.
The color formers are employed either in the emulsion or in the developer. However, where they contain a group preventing diffusion, they are preferably used in the emulsion. Examples of compounds falling'within such category are compounds 8 and 11 above.
The color developers which are employed are, as stated, of the ortho-phenylenediamine type, a number of examples of which are referred to in the aforesaid Schmidt and Tulagin application. Suitable developers of this class are:
4;.6:-dianilino ,metanilic acid 4.6 bis (p methoxy phenylamino) -metanilic acid 4 (o methoxy' phenylamino) 6 -(p-methoxyphenylamino) -metani1ic acid 4.6-bis-(o-methoxy phenylamino-metanilic acid 4 (p-sulfo-phenylamino)-6-dimethylamino metanilic acid, and the like.
The invention may be efiectuated so as to use the color developing method for producing 001- ored negatives, colored positives, or reversed images. These general methods are conventional in the art, being dependent for their efficacy upon the point at which color development takes place.
The invention is further illustrated by the following examples, but it is to be understood that the invention is not restricted thereto.
Example 1 To 1 kilo of a silver bromide iodide emulsion is added .7 gram of Z-methyll-(4-N-tetradecylsulfoacetamido-aniline)-4'hydroxy-7.8 benzoquinoline, and the mixture is coated on a suitable support. The resulting film is exposed and developed in a black and white developer. The film is thoroughly washed and the residual silver halide re-exposed and developed in a developer of the following composition:
4.6-dianilino metanilic acid grams 1.5 Sodium sulfite do 60 Potassium carbonate do 40 Pyridine cubic centimeters 12 Water do 1000 The film is washed, bleached and fixed in the conventional manner to yield cyan phenazonium dyestufi images of high contrast.
Example 2 A silver bromide emulsion is exposed and color developed in a developer of the following constitution:
4.6-dianilino metanilic acid "grams" 1.5 Sodium sulfite do Potassium carbonate do 40 Pyridine cubic centimeters 12 2-methy1l.5-dihydroxy-7.8-benzoquinoline grams 1 Water cubic centimeters 1000 The film is washed, bleached and fixed in the customary manner. A negative cyan phenazonium dyestuif image remains.
The following table illustrates the color of the dyestuff images obtained when using other color formers with the developer of Example 1:
Table. l
. Color of Formed Coupler Dye 2-methyl-4.4-dihydroxy7.8-benzoquinoline 2. i-dihydroxy-4-methyl-7.S-benzoquinoline, 2-methyl-4(4"-arsonoanilino)-4-hydroxy 7.8-benzoquinoline. 2-methy1-4 (4-si 1lloanilino) 4-hydroxy-7.8-benzoquinollne. 2-methyl-4 (4@eulfcacetamidoaniline) -4-hydroxy- 7.8-benzoquinoline. 7
Greenish blue.
wherein R is an auxochromic group selected from the class consisting of hydroxy and amino groups, R1 is lower alkyl, the OH indicated in the formula is in the B-position of the designated benzo ring and R and R1 are both in the heterocyclic ring.
2. The process as defined in claim 1, wherein the color former is 2-methy1-4,5-dihydroxy-7.8- benzoquinoline.
3. The process as defined in claim 1, wherein the color former is 2-methyl-4-(4"-tetradecylsulfoacetamidoaniline) -4'-hydroxy 7.8 benzoquinoline.
4. A photographic silver halide emulsion containing as a color former capable of yielding cyan phenazonium dyestuff images when color developed with an ortho-phenylenediamine type developer a compound selected from the group and and
where R is an auXochromic group selected from the class consisting of hydroxy and. amino groups, R1 is lower alkyl, the OH indicated in the formula is in the [3-position of the designated benzo ring and R and R1 are both in the heterocyclic ring, said compound being free from groups rendering said compound non-diffusing in photographic emulsions.
6. The photographic developer of claim 5 wherein the color former is 2-methyl-4.5'-dihydroxy-7 .8-benzoquinoline.
'7. The photographic silver halide emulsion defined in claim 4 wherein the color former is 2- methyl-4-(4"-N tetradecyl-sulfoacetamidoaniline) -4-hydroxy-7.8-benzoquinoline.
VSEVOLOD TULAGIN. WILLY. A. SCHMIDT.
Name Date Frohlich et a1 Mar. 9, 1943 Number

Claims (1)

1. THE PROCESS OF PRODUCING CYAN PHENAZONIUM DYSTUFF IMAGES BY COLOR FORMING DEVELOPMENT WHICH COMPRISES EXPOSING A SILVER HALIDE EMULSION AND DEVELOPING THE SAME WITH AN ORTHOPHENYLENEDIAMINE TYPE DEVELOPER IN THE PRESENCE OF COLOR FORMER SELECTEDC FROM THE GROUP HAVING THE FOLLOWING FORMULAS:
US793534A 1946-01-10 1947-12-23 Production of phenazonium dyestuff images Expired - Lifetime US2525502A (en)

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US640382A US2486440A (en) 1946-01-10 1946-01-10 Production of phenazonium dyestuff images

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US640382A Expired - Lifetime US2486440A (en) 1946-01-10 1946-01-10 Production of phenazonium dyestuff images
US793534A Expired - Lifetime US2525502A (en) 1946-01-10 1947-12-23 Production of phenazonium dyestuff images
US793536A Expired - Lifetime US2524725A (en) 1946-01-10 1947-12-23 Magenta phenazonium dyestuff images from 8-hydroxyquinoline couplers
US793535A Expired - Lifetime US2525503A (en) 1946-01-10 1947-12-23 Production of phenazonium dyestuff images
US793533A Expired - Lifetime US2524741A (en) 1946-01-10 1947-12-23 Magenta phenazonium dyestuff images from 6-substituted-8-hydroxyquinoline couplers
US101913A Expired - Lifetime US2570116A (en) 1946-01-10 1949-06-28 Color developers for the production of azine dye images

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US793536A Expired - Lifetime US2524725A (en) 1946-01-10 1947-12-23 Magenta phenazonium dyestuff images from 8-hydroxyquinoline couplers
US793535A Expired - Lifetime US2525503A (en) 1946-01-10 1947-12-23 Production of phenazonium dyestuff images
US793533A Expired - Lifetime US2524741A (en) 1946-01-10 1947-12-23 Magenta phenazonium dyestuff images from 6-substituted-8-hydroxyquinoline couplers
US101913A Expired - Lifetime US2570116A (en) 1946-01-10 1949-06-28 Color developers for the production of azine dye images

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BE (6) BE470459A (en)
CH (5) CH280516A (en)
DE (6) DE851163C (en)
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US2717831A (en) * 1953-02-24 1955-09-13 Gen Aniline & Film Corp Benzo(h)quinolin-ols as azine cyan color formers
US4511569A (en) * 1982-08-26 1985-04-16 Schering Corporation Tricyclic lactams and derivatives useful in increasing cardiac contractility
US4612316A (en) * 1983-04-27 1986-09-16 Astra Lakemedel Aktiebolag Tricyclic amines with central dopaminergic activity
US4990436A (en) * 1990-01-23 1991-02-05 Eastman Kodak Company Cyan dye-forming couplers and photographic recording materials containing same
US5260177A (en) * 1988-03-16 1993-11-09 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material

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CH277023A (en) * 1949-05-03 1951-08-15 Ciba Geigy Process for the production of an intermediate product.
US2575027A (en) * 1949-10-29 1951-11-13 Gen Aniline & Film Corp N-substituted 4, 6-diamino metanilic acids
US2596926A (en) * 1949-12-16 1952-05-13 Gen Aniline & Film Corp Preparation of azine dye images
US2594917A (en) * 1949-12-16 1952-04-29 Gen Aniline & Film Corp Suppression of proximity development with azine color developers
US2623823A (en) * 1950-03-21 1952-12-30 Gen Aniline & Film Corp Energizers for aromatic triamino developing agents and suppression of proximity development in azine color developers
US2618559A (en) * 1950-03-21 1952-11-18 Gen Aniline & Film Corp Stain preventing shortstop bath for photographic azine dye images
US2687431A (en) * 1950-12-20 1954-08-24 Gen Aniline & Film Corp Process of preparing nitro phenylenediamines
BE508676A (en) * 1951-01-26
US2691588A (en) * 1952-03-14 1954-10-12 Eastman Kodak Co Photographic developers containing 8-hydroxyquinolines
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
GB802553A (en) * 1955-11-18 1958-10-08 Gen Aniline & Film Corp Improvements in or relating to colour photographic materials and processes
US2945761A (en) * 1957-07-29 1960-07-19 Eastman Kodak Co Reactivity of couplers incorporated in photographic emulsions
DE1069470B (en) * 1958-04-03 1959-11-19 General Aniline &. Film Corporation, New York, N. Y. (V.St.A.) Photographic silver halide emulsion or developer with a color former which, after color development with a developer of the p-phenylenediamine rub, gives a yellow azine color image
US3099559A (en) * 1959-08-31 1963-07-30 Gen Aniline & Film Corp Silver-free color reproduction process and composition therefor
BE594935A (en) * 1959-09-11
US3050394A (en) * 1959-09-30 1962-08-21 Gen Aniline & Film Corp Method of incorporating color couplers in hydrophlic colloids
US3077403A (en) * 1960-05-31 1963-02-12 Gen Aniline & Film Corp Color former containing bis coupling functions
JPS59177554A (en) * 1983-03-28 1984-10-08 Fuji Photo Film Co Ltd Silver halide color photosensitive material
US4680299A (en) * 1984-04-30 1987-07-14 E.I. Du Pont De Nemours And Company 2-phenyl-4-quinolinecarboxylic acids and pharmaceutical compositions thereof
US4847381A (en) * 1987-08-31 1989-07-11 American Cyanamid Company 2-Phenyl-4-quinoline carboxylic acids
US5223386A (en) * 1989-03-04 1993-06-29 Konica Corporation Cyan coupler
EP0386931A1 (en) * 1989-03-04 1990-09-12 Konica Corporation A novel cyan coupler

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Cited By (5)

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Publication number Priority date Publication date Assignee Title
US2717831A (en) * 1953-02-24 1955-09-13 Gen Aniline & Film Corp Benzo(h)quinolin-ols as azine cyan color formers
US4511569A (en) * 1982-08-26 1985-04-16 Schering Corporation Tricyclic lactams and derivatives useful in increasing cardiac contractility
US4612316A (en) * 1983-04-27 1986-09-16 Astra Lakemedel Aktiebolag Tricyclic amines with central dopaminergic activity
US5260177A (en) * 1988-03-16 1993-11-09 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4990436A (en) * 1990-01-23 1991-02-05 Eastman Kodak Company Cyan dye-forming couplers and photographic recording materials containing same

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GB646348A (en) 1950-11-22
GB646490A (en) 1950-11-22
DE854889C (en) 1952-11-06
FR61006E (en) 1955-03-23
DE850385C (en) 1952-09-25
DE848155C (en) 1952-11-04
BE486430A (en) 1949-01-16
US2486440A (en) 1949-11-01
FR61007E (en) 1955-03-23
DE837959C (en) 1952-05-05
US2570116A (en) 1951-10-02
CH283787A (en) 1952-06-30
BE486431A (en) 1948-12-21
FR61004E (en) 1955-03-23
FR58855E (en) 1954-04-06
FR939497A (en) 1948-11-16
DE817554C (en) 1951-10-18
BE486434A (en) 1949-01-15
CH280518A (en) 1952-01-31
BE486433A (en) 1949-01-15
US2524741A (en) 1950-10-03
DE851163C (en) 1952-10-02
FR61005E (en) 1955-03-23
CH280517A (en) 1952-01-31
GB649811A (en) 1951-01-31
GB647638A (en) 1950-12-20
GB644863A (en) 1950-10-18
CH283788A (en) 1952-06-30
BE470459A (en) 1947-02-28
US2525503A (en) 1950-10-10
BE486432A (en) 1949-01-15
CH280516A (en) 1952-01-31
US2524725A (en) 1950-10-03

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