US3080233A - Method of incorporating metal salts of color couplers in photographic emulsions - Google Patents

Method of incorporating metal salts of color couplers in photographic emulsions Download PDF

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US3080233A
US3080233A US809926A US80992659A US3080233A US 3080233 A US3080233 A US 3080233A US 809926 A US809926 A US 809926A US 80992659 A US80992659 A US 80992659A US 3080233 A US3080233 A US 3080233A
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solution
mixture
photographic
added
water
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Curt B Roth
Fritz W H Mueller
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GAF Chemicals Corp
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General Aniline and Film Corp
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Priority to BE590403D priority Critical patent/BE590403A/xx
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Priority to US809926A priority patent/US3080233A/en
Priority to GB12890/60A priority patent/GB902266A/en
Priority to DEG29573A priority patent/DE1120274B/de
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
    • 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
    • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor

Definitions

  • This invention relates to color photography and in particular to photographic emulsions for color photography containing the alkali metal salts of color formers or couplers incorporated therein by means of Water miscible solvents.
  • Photographic emulsions are described containing thereina coupler compound of the type capable of coupling with the oxidation products of a primary aromatic amino developing agent whereby is produced a colored photographic image.
  • the coupler compounds can be incorporated therein.
  • an aqueous solution of the coupler compound is dissolved directly in the hydrophilic colloid of the photographic emulsion.
  • Such couplers commonly contain, in addition to a non-difiusing group, a sulfonic acid or carboxylic acid grouping and are employed in the form of their alkali metal salts.
  • couplers of this type can be attributed to the presence of the non-diffusing group.
  • an object of the present invention to provide a novel means of incorporating the alkali metal or ammonium salts of colored or colorless couplers containing acidic groups in photographic emulsions.
  • the aforesaid objects can be accomplished by dissolving a color coupler of the type described herein in the form of its alkali metal salt in a water soluble or water miscible solvent for said alkali metal coupler salt and dispersing the resulting solvent solution of the coupler salt in a photographic colloid.
  • the Water soluble or Water miscible solvent is then removed from the alkali metal coupler salt dispersion incorporated in a hydrophilic colloid silver halide emulsion.
  • the dispersions of the alkali metal coupler salts obtained as described above consist of extremely finely divided particles which display no tendency to settle out or coalesce. Such dispersions of alkali metal coupler salts can be stored indefinitely in the chilled state prior to the coating operation.
  • the couplers used in our process are characterized by the presence of a salt-form- 2 ing group, i.e., a carboxylic acid or sulfonic acid group, and a non-difiusing group such as an aliphatic chain of at least 10 carbon atoms.
  • a salt-form- 2 ing group i.e., a carboxylic acid or sulfonic acid group
  • a non-difiusing group such as an aliphatic chain of at least 10 carbon atoms.
  • Such couplers are further characterized in that their alkali metal salts are not sufficiently soluble in aqueous systems or require prohibitively high pH values in order to eifect their incorporation directly in a hydrophilic photographic colloid.
  • Couplers which we have found particularly suitable in this connection contain, as the non-diffusing group, an alkyl radical of at least 10 carbon atoms in which a salt-forming radical is located on the terminal carbon atom of said alkyl group. These couplers can be depicted by the following general formula:
  • M represents a hydrogen, ammonium or an alkali metal
  • R represents a coupler molecule of the type containing a reactive methylene or phenolic hydroxy group
  • n represents a positive integer of 9 or more.
  • reactive methylene group is meant the type commonly encountered incolor couplers and which can be depicted by the following general formula:
  • X arid Y stand for electron attracting groups such as carbonyl, cyano, nitr'o and the like.
  • By'pheriolic hydroir'y group is meant the phenolic phe'uyl' gfeu' 's commonly understood in the color coupler art and includes the phenolic or hydroXy naphtho'ic types having [a rea'c tive position para to the said hydroxy group, that is, a position which is unsubstituted or which is substituted with a replaceable group.
  • the aforesaid groups are well recognized in the photographic fild so that further discussion of such entities would be superfluous.
  • a photographic emulsion is prepared for coating by adding a solution of the alkali metal salt of the coupler in a water soluble solvent directly to a melted gelatino silver halide emulsion under efiicient agitation with a laboratory type mixer such as a Waring Blendor.
  • the color former is first dissolved in a water miscible solvent such as dimethylformamide and this solution is added to an aqueous gelatin solution under vigorous agitation.
  • a water miscible solvent such as dimethylformamide
  • the thusly obtained mixture is then chilled, noodled and washed after which it is com bined with a liquified photographic gelatino silver halide emulsion.
  • the sensitive emulsion is coated after the addition of the customary stabilizers, preservatives and spreading agents in the usual manner on a conventional film base of the type commonly employed in the art such as cellulose acetate, polyester, i.e., polyethyleneterephthalate, polycarbonte, polyamide or paper, glass or the like.
  • a film base should be selected of a type which is not deleteriously eitected by the action of the water miscible solvents used to dissolve the alkali meta-l salt of the coupler.
  • polyester or polycarbonate film base as well as paper or glass are suitable.
  • the photographic coatings prepared according to the process described herein produce, on color development, very sharp colored images and display no undesirable side effects such as desensitization or fogging during storage or processing. It is not known, at the present time, if the alkali metal salt of the color former, when in corporated in a hydrophilic colloid in accordance with our invention, represents a true solution or is in such a state of fine division as to constitute a colloidal dispersion or, perhaps, a superfine dispersion. Examples of the Washed emulsions have been examined under the microscope at high magnification, i.e., in the neighborhood of 900 diameters, and there was no evidence to indicate the presence of discrete coupler particles. The extremely fine state of division of the alkali metal salt couplers is borne out by the virtually grainless dye images which they yield upon color development, that is, no dye clumps can be discerned when the developed images are subjected to microscopic examination.
  • the alkali metal and ammonium salts of color formers of the type contemplated herein are either insoluble in a photographic colloid emulsion or require excessively high alkalinity in order to efiect their dissolution in this type of medium. Neither can such color-forming components be incorporated in a photographic emulsion by the well known lip-ophilic dispersion techniques since these coupler salts are too insoluble in the water immiscible oils commonly used for such lipophilic dispersion procedures.
  • the method disclosed herein offers the sole means of utilizing valuable colorforming components, i.e., the aforesaid alkali metal or ammonium salts, which cannot be incorporated in a photographic emulsion by methods presently known to the art.
  • the photographic emulsions containing metal salts of color former can be prepared by two general methods.
  • a di alkylformamide solution such as a dimethylformamide solution of the color former is added directly to a melted gelatino silver halide emulsion While stirring with a laboratory type mixer such as, for instance, a Waring Blendor.
  • the solution of color former in dialkylformamide is first dissolved in an aqueous solution of a hydrophilic colloid such as gelatin and the resultant mixture combined with a melted gelatino silver halide emulsion.
  • the color former is first dissolved in dimethylformarnide and this solution is added to an aqueous gelatin solution and thoroughly agitated in a laboratory type mixer or stirrer. The resulting mixture is washed and then combined with a photographic gelatino silver halide emulsion, chilled and the sensitive emulsion then coated in the usual manner on a conventional base such as that of cellulose acetate, polyester, i.e. polyethyleneterephthalate, polycarbonate, polyamide or paper, glass or the like.
  • the dialkylformamide solution would be dispersed or emulsified when agitated with the hydrophilic colloid.
  • Photographic films prepared in accordance with the present invention are, when wet, not very hazy or frosty in appearance, a property characteristic of fihns using dispersion methods of the prior or present art.
  • Example 1 This example illustrates the method used by us in incorporating a cyan color former in a photographic emulsion.
  • the particular color former used in this example has the formula:
  • Example 2 720 milligrams of color former from Example 1 were dissolved in 7 ml. of dimethylformamide, 4 drops of Tergitol NPX added and the mixture filtered. Separately, a 10% aqueous solution of an inert gelatin in water was prepared at 55 C. To 30 ml. of this 10% gelatin solution were added 4 drops of Tergitol #4. The solution was placed into a speed mixer (Waring Blendor, kitchen type). After 30 seconds at full speed, the filtered dimethylforrnamide solution was slowly added over a period of 30 seconds with the mixer running at 30 volts. After the two solutions were combined, the mixer was run at full speed for 60 seconds.
  • a speed mixer Waring Blendor, kitchen type
  • the milky-looking product can be used as is or the dimethylformamide can be washed out.
  • 'To wash the dimethylformamide out the emulsion was chilled, shredded and then washed by downward replacement washing for 6 hours'with cold water (8 C.). The washed product was then mixed into a photographic emulsion and evaluated as in'Examp'le 1.
  • Example 3 4 ml. of dimethylformarnide.
  • Tergitol produces a finer dispersion of color former and dye in the gelatin. Note that no alkali was used in these examples. The use of alkali produces a yellowish looking product and is detrimental as a-rule.
  • Example 8 This example illustrates the incorporation of a magenta color former in a photographic emulsion.
  • the particular color former used in this case has the formula:
  • the mixer was then run for 30 seconds at 120 volts. Then, 4 drops of a aqueous solution of sodium hydroxide were added over a period of 5 seconds with the mixer running at 90 volts. Mixing was continued for seconds at 90 volts. The clear yellow product was transferred into a tray and allowed to cool. The chilled gelatinous product was cut into small noodles which were Washed for 18 hours with cold water (8-l2 C.). The washed noodles were then remelted at 40 C. and added to 50 g. of photographic emulsion containing O.6 ml. of an 8% aqueous solution of saponin as a spreading agent. Other adjuncts such as sensitizing dyes, stabilizers, etc., may be added at this point. The 40 C. warm mixture was then coated onto a film support.
  • Example 9 The magenta color former of the following formula was used in this example.
  • the product was poured into a 8 tray and allowed to cool to room temperature. After chilling, the product was cut into small noodles with a knife. These noodles were then washed for 18 hours with cold (812 C.) water. After draining of the excess water, the noodles were remelted at 40 C. and added in darkness to 50 g. of a color type photographic emulsion.
  • This emulsion contained 0.6 ml. of an 8% aqueous solution of saponin besides the usual adjuncts such as sensitizing dyes, stabilizers, etc.
  • the final mixture was coated at 40 C. onto a photographic film support as is customary inthe art.
  • Example 10 This example illustrates a method of incorporating a yellow color former in a photographic emulsion.
  • the color former used in this example has the formula:
  • This special funnel consisted of a Pyrex glass funnel of 39 mm. diameter whose stem had been drawn out to a small opening of 1 mm. diameter. Into the stem was packed some cotton to filter out mechanical impurities and to regulate the flowing time. The addition was made over a period of 360 seconds with the mixer running at 30 volts. Mixing was continued for 30 seconds with the mixer running at volts. The yellow, slightly opaque product was then poured into a dish and allowed to cool. The chilled product was then cut into small noodles and washed for 48 hours with slow-running cold (812 C.) water. The noodles were then remelted and added to 50 g.
  • a photographic emulsion This emulsion had been designed for the yellow layer and contained, besides the usual finals, 1.0 ml of an aqueous 8% saponin solution and 2 drops of Pluronic lr61. The mixture was then coated onto a film base as is customary in the art.
  • Tergitol NPX is alkylphenyl polyethylene glycol ether and is sold by the Carbide and Carbon Chemical Company, 30 E. 42nd Street, New York 17, New York.
  • Tergitol #4 is sodium tetradecyl sulfate and is sold as a 25% solution by the Carbide and Carbon Chemical Company, 30 E. 42nd Street, New York 17, New York.
  • Pluronic L-61 is a polymer prepared by adding propylene oxide to the two hydroxyl groups or" a propylene glycol nucleus until the desired molecular weight is achieved. Ethylene oxide is then added to both ends of the above polymer until the desired ratio of polyoxyethylene to polyoxypro-pylene units is obtained.
  • Pluronic L-61 is composed of a polyoxypropylene fragment with a molecular weight of 1750 while 10% of the total molecular weight "abscess G. 2-arnino-5-diethylamino toluene HCI 2 Sodium sulfite, anhydrous '2 Sodium carbonate, monohydrate, '2 Potassium bromide 2 Sodiumhydroxide to give .pH 10.8. Water to 1 liter.
  • Reaction B was then carried out as follows:
  • the mixture was refluxed overnight and then rendered alkaline against phenolphthalein with 40% aqueous sodium hydroxide.
  • the solution was filtered through a Buckner funner and the filtrate acidified with glacial acetic acid. The resulting precipitate was filtered ofi after coolmg.
  • REACTION B 45 grams of iron powder (40 mesh) and 15 ml. of concentrated hydrochloric acid were mixed into a 3-neck, 1- liter round bottom flask provided with a stirrer and a reflux condenser. After 5 minutes, 100 ml. of water and 400 ml. of ethanol were added and the mixture heated to reflux temperature with vigorous mechanical stirring. 32 grams (about 0.1 mole) of the previously prepared airdried and powdered nitro compound was then slowly added to the stirred, boiling reducing mixture over a period of 1 hour. The suspension was then refluxed, with efficient stirring, for 18 hours. The aqueous phase was made alkaline with aqueous, 6 N sodium hydroxide solution.
  • the washed product was recrystallized once with a solution containing 400 ml. of concentrated hydrochloric acid, 400 ml. of water and 40 g. of potassium chloride.
  • the crystalline material was filtered again by means of a Buchner funnel and washed on the funnel with the following solvents: Twice with ml. each, of ice water, twice with 100 ml, each, of methanol and twice with 100 ml., each, of et er. Yields of various batches: 117 g., 119 g. and 128 g.; melting point 193-197 C.
  • the melting point range of the analytical sample was 195-197" C.
  • the product obtained was:
  • the product obtained was:
  • CONHGCH1 SOaNa(CHz) 106 ()NH spouses 40 ml. of dry benzene added dropwise with rapid stirring. This required about 1 hour.
  • the mixture was refluxed for 2 hours on a steam bath and to the still hot mixture was added a solution of 4.5 g. of sodium hydroxide and 11 g. of sodium acetate (anhydrous) in 40 ml. of water.
  • the mixture was then cooled, filtered and dried in a vacuum desiccator over concentrated sulfuric acid.
  • the product was purified by dissolving it in 250 ml. of hot 70% methanol which had previously been adjusted to a pH of 9 with 2 N sodium hydroxide and precipitating it with 5 N hydrochloric acid after filtration.
  • the mixture was refluxed for 2 hours on a steam bath and a solution of 8 g. of sodium hydroxide and 21 g. of anhydrous sodium acetate in 50 ml. of water was added to the hot mixture.
  • the flask was stored in a refrigerator for hours and the contents then filtered on a Buchner funnel and dried in a vacuum desiccator over sulfuric acid. Recrystallization from three times 80% acetic acid. Yield 23 g. of purified product.
  • the compound produced was:
  • REACTION B 300 grams of iron powder (40 mesh), 160 ml. of hydrochloric acid, 400 ml. of water and 2000 ml. of ethanol were charged in a 3-liter, 3-neck round bottom flask equipped with stirrer and reflux condenser. To the refluxing mixture, 170 g. of the above nitro compound from reaction A was added in small portions, always maintaining an excess of Fe++. The mixture was refluxed overnight, rendered alkaline against phenolphthalein with 50% sodium hydroxide, filtered and acidified with dry acetic acid. The nearly white precipitate was filtered ofii.
  • the compound produced was:
  • the mixture was refluxed on a steam bath for 2 hours. Then, a solution of 12 g. of sodium hydroxide and 30 g. of sodium acetate in 50 ml. of water was added. The reaction product was stored for 15 hours in a refrigerator, filtered on a Buchner funnel and recrystallized from acetic acid.
  • the compound produced was:
  • R represents a coupler molecule of the type capable of coupling with the oxidation prod ucts of a primary aromatic amino developing agent, said coupler molecule being selected from the class consisting f l-hydroxy-Z-naphthoic radicals, OL-bCl'lZOyl acid anilide radicals, and 3-(l-phenyl-S-pyrazolone) radicals and n represents a positive integer of at least 9 which comprises dissolving said coupler salt in dimethylformamide, mixing the resulting solution of said coupler with a solution of the hydrophilic colloid used in the preparation of the hydrophilic emulsion, setting the resulting dispersion, shredding the set dispersion, washing the shredded set dispersion to remove the dimethylformamide therefrom and mixing the washed dispersion with the said photographic silver halide hydrophilic,

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US809926A 1959-04-30 1959-04-30 Method of incorporating metal salts of color couplers in photographic emulsions Expired - Lifetime US3080233A (en)

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BE590403D BE590403A (en。) 1959-04-30
US809926A US3080233A (en) 1959-04-30 1959-04-30 Method of incorporating metal salts of color couplers in photographic emulsions
GB12890/60A GB902266A (en) 1959-04-30 1960-04-11 Method of incorporating salts of color couplers in photographic emulsions
DEG29573A DE1120274B (de) 1959-04-30 1960-04-30 Verfahren zur Einverleibung eines Salzes eines Farbkupplers in photographische Emulsionen

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3135609A (en) * 1960-06-29 1964-06-02 Gen Aniline & Film Corp 1-hydroxy-2-naphthamide couplers for color photography
US3161512A (en) * 1959-12-23 1964-12-15 Ilford Ltd Colour couplers and their production and use in colour photography
US5300418A (en) * 1992-04-16 1994-04-05 Eastman Kodak Company Viscosity control of photographic melts
WO2012140647A3 (en) * 2011-04-11 2013-03-28 Yeda Research And Development Co. Ltd Albumin binding probes and drug conjugates thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3622337A (en) * 1968-08-02 1971-11-23 Gaf Corp Cyan color formers for color photography

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2498466A (en) * 1946-05-09 1950-02-21 Gen Aniline & Film Corp Phenolic color formers
US2533514A (en) * 1947-11-19 1950-12-12 Eastman Kodak Co Photographic emulsions containing color couplers and amide coupler solvents
US2829975A (en) * 1956-04-26 1958-04-08 Gen Aniline & Film Corp 3-alpha-sulfo acylamino pyrazolone color formers in which the acyl group contains a long aliphatic chain
US2902366A (en) * 1956-10-23 1959-09-01 Gen Aniline & Film Corp Acylated 3-aminopyrazolone couplers

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE695980C (de) * 1935-04-12 1940-09-07 I G Farbenindustrie Akt Ges Verfahren zur Herstellung von Gelatineloesungen bzw. von Halogensilberemulsionen in Gelatine fuer photographische Zwecke, die ein oder mehrere wasserunloesliche Farbstoffzwischenprodukte enthalten
US2346080A (en) * 1942-06-12 1944-04-04 Eastman Kodak Co Acylaminohydroxydiphenyl coupler
BE483861A (en。) * 1947-07-11
US2772162A (en) * 1954-11-03 1956-11-27 Eastman Kodak Co Diacylaminophenol couplers
BE543744A (en。) * 1954-12-20
BE572971A (en。) * 1957-11-14

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2498466A (en) * 1946-05-09 1950-02-21 Gen Aniline & Film Corp Phenolic color formers
US2533514A (en) * 1947-11-19 1950-12-12 Eastman Kodak Co Photographic emulsions containing color couplers and amide coupler solvents
US2829975A (en) * 1956-04-26 1958-04-08 Gen Aniline & Film Corp 3-alpha-sulfo acylamino pyrazolone color formers in which the acyl group contains a long aliphatic chain
US2902366A (en) * 1956-10-23 1959-09-01 Gen Aniline & Film Corp Acylated 3-aminopyrazolone couplers

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3161512A (en) * 1959-12-23 1964-12-15 Ilford Ltd Colour couplers and their production and use in colour photography
US3135609A (en) * 1960-06-29 1964-06-02 Gen Aniline & Film Corp 1-hydroxy-2-naphthamide couplers for color photography
US5300418A (en) * 1992-04-16 1994-04-05 Eastman Kodak Company Viscosity control of photographic melts
WO2012140647A3 (en) * 2011-04-11 2013-03-28 Yeda Research And Development Co. Ltd Albumin binding probes and drug conjugates thereof
US9480751B2 (en) 2011-04-11 2016-11-01 Yeda Research And Development Co. Ltd. Albumin binding probes and drug conjugates thereof

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BE590403A (en。)
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