US3591384A - Silver halide emulsion containing naphthamide photographic couplers - Google Patents

Silver halide emulsion containing naphthamide photographic couplers Download PDF

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Publication number
US3591384A
US3591384A US701995A US3591384DA US3591384A US 3591384 A US3591384 A US 3591384A US 701995 A US701995 A US 701995A US 3591384D A US3591384D A US 3591384DA US 3591384 A US3591384 A US 3591384A
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US
United States
Prior art keywords
coupler
couplers
silver halide
photographic
naphthamide
Prior art date
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Expired - Lifetime
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US701995A
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English (en)
Inventor
Alberto Guzzi
Remo Magagnoli
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Ferrania SpA
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Ferrania SpA
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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
    • G03C7/34—Couplers containing phenols
    • G03C7/344—Naphtholic couplers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring

Definitions

  • the cyan couplers of this invention have the formula:
  • X is alkyl, preferably a lower alkyl (C -C Y f P couplers h e the general e m is either carbonyl or sulfonyl, R is C -C alkyl, and Z is r X hydrogen or halogen, preferably chlorine or bromine.
  • g i r 1 These couplers are easily obtained in a'very high purity by methods described later. 20 Illustrative couplers are as follows:
  • V -CONH This invention relates to a class of couplers capable of forming stable cyan or blue-green dyes by color development in color photographic materials.
  • the dispersed coupler method in which the coupler is dissolved in high boiling organic solvents, such as tricresyl 01 3010181138 phosphate or dibutyl phthalate, and the resulting solution Table I shows some analytical data of these illustrais intimately dispersed throughout the silver halide emultive couplers, the analyses being made after only one cryssi on To obtain the best results in terms of the dispersion tallization of the raw reaction product. Included are their and photographic efficiency the solution of coupler in the desirable melting points. Their high degree of solubility organic solvent should be highly concentrated.
  • Couplers in organic solvents normally used for dispersing couplers which are highly soluble in or miscible with the organic in a gelatin emulsion permits the use of a solvent/coupler solvent are therefore commonly selected for use in disratio far lower than 1.0 without any noticeable decrease persed coupler systems.
  • couplers having a relain yield of dye formed by normal color development protively low melting point are quite soluble in such organic cedures.
  • coupler (l) can be incorporated solvents.
  • the claimed couplers react with N,N-dialkyl-p-phenylenediamine during color development to provide dyes which are particularly stable to light, heat and moisture.
  • N,N-dialkyl-p-phenylenediamine for example, if one of thesecouplers is dissolved in dibutyl phthalate, dispersed in a photographic emulsion, coated onto a transparent support, exposed and developed with diethyl p phenylenediamine, the resultant color shows no noticeable change in either color density or hue after exposure to a xenon lamp for 10 hours.
  • Coated samples prepared insimilar manner were exposed through a scale of decreasing densities, i.e. grey scale, and developed in color developer with. excellent sensitometric results, even after storage for 2 hours at 'a temperature of 194.0 F.
  • curve A is the sensitometric curve '(read in red light) for coupler (1) and curve B is the sensitometric curve for coupler (1) after 24 hours storage under the abovementioned conditions.
  • curve B shows the excellent stability of dyes prepared from the couplers of this invention.
  • the spectral absorption of the cyan dyes obtained from these couplers and N,N-dialkyl-p-phenylenediamine developers make then particularly suitable for preparing color negative materials. Furthermore, they have a low absorption in the green portion of the spectrum, which is very desirable.
  • the coupler of curve B is a known coupler having some strutural similarity to the couplers of this invention. From a comparison of curves A and B it is apparent that curve A represents lower absorption in the 500 and 600 millimicron region than curve B.
  • the coupled was obtained by the reaction of the raw amine with phenyl l-hydroxy-Z-naphthoate and, after crystallization from ethanol, the M.P. was 273.2-277.5 F. (l34-l36.5 C.).
  • Example 1 2 grams of coupler (1) was dissolved in a mixture consisting of 0.5 ml. of dibutyl phthalate and 12 ml. of ethyl acetate by heating on a boiling water bath. The resulting clear solution was poured into 40 ml. of 4% gelatin containing 4 ml. of sodium tetradecyl sulfate solution. At a temperature of about 104.0 F. (40 C.) the mixture was dispersed in a homogcnizer. The dispersion thus obtained was added to 200 g. of silver halide photographic emulsion sensitized to red light. The thus modified emulsion was spread on a transparent support, dried and exposed through an original.
  • Example 2 A dispersion of the following formulation:
  • X is lower alkyl
  • Y is carbonyl or sulfonyl
  • R is an alkyl group having from 5 to 20 carbon atoms
  • Z is hydrogen or halogen
  • a photographic element having at least one layer comprising the emulsion of claimv 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US701995A 1967-02-15 1968-01-31 Silver halide emulsion containing naphthamide photographic couplers Expired - Lifetime US3591384A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT3484667 1967-02-15

Publications (1)

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US3591384A true US3591384A (en) 1971-07-06

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US701995A Expired - Lifetime US3591384A (en) 1967-02-15 1968-01-31 Silver halide emulsion containing naphthamide photographic couplers

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US (1) US3591384A (enrdf_load_html_response)
BE (1) BE710718A (enrdf_load_html_response)
CH (1) CH514161A (enrdf_load_html_response)
FR (1) FR1564654A (enrdf_load_html_response)
GB (1) GB1221803A (enrdf_load_html_response)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3692833A (en) * 1967-02-15 1972-09-19 Alberto Guzzi Photographic color couplers
US5508148A (en) * 1994-12-19 1996-04-16 Eastman Kodak Company Photographic element containing a novel cyan dye forming coupler and process for its use

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2201208A1 (de) * 1972-01-12 1973-08-02 Basf Ag Verfahren zur herstellung von aromatischen ketonen
IT1229993B (it) * 1989-03-09 1991-09-20 Minnesota Mining & Mfg Materiali fotografici a colori agli alogenuri d'argento.

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3692833A (en) * 1967-02-15 1972-09-19 Alberto Guzzi Photographic color couplers
US5508148A (en) * 1994-12-19 1996-04-16 Eastman Kodak Company Photographic element containing a novel cyan dye forming coupler and process for its use

Also Published As

Publication number Publication date
FR1564654A (enrdf_load_html_response) 1969-04-25
DE1622300A1 (de) 1970-12-23
BE710718A (enrdf_load_html_response) 1968-06-17
DE1622300B2 (de) 1976-04-08
GB1221803A (en) 1971-02-10
CH514161A (it) 1971-10-15

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