Classifications

• • 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
  • G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
  • G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
  • G03C7/30517—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution
  • G03C7/30535—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution having the coupling site not in rings of cyclic compounds
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
  • Y10S430/149—Lippmann

Definitions

• ABSTRACT Color developer compositions which contain, dissolved therein, both (a) an organic aromatic primary amino developing agent and (b) a yellow-dye-forming coupler having the structure:
• R is a branched alkyl group containing 3 to 6 carbon 10 atoms; X is C1 or Br; Y is X, hydrogen or I alkyl (1 to 8 carbon atoms); and A and B differ and are either H or -COOM, wherein M is a photographically inactive cation or a methyl or ethyl group.
• Use of such compositions results in more efficient coupler usage and color products having yellow dyes with improved aging characteristics.
• the invention encompasses such liquid developer compositions, blends of (a) and (b), and the yellow dye-forming couplers, per
• the present invention relates to developer compositions containing such valuable diffusible yellow-dye-forming coupler materials.
• the coupler compounds of this invention are haloanilidophenoxycarboxy compounds having the structure I:
• R is a branched alkyl group containing 3 to 6 carbon atoms: X is Cl or Br; Y is X, hydrogen or alkyl (1 to 8 carbon atoms); and A and B differ and are either H or -COOM, wherein M is a photographically inactive cation, a methyl group or an ethyl group.
• This invention also includes developer compositions containing one or more of the compounds ofthe structure I l and one or more organic aromatic amino developing agents, which developer compositions are used in the form of aqueous solutions comprising water and having a pH ofat least about 10.
• color-forming coupler compounds have been classified as incorporated" and diffusible", based upon the way such compounds are ordinarily used.
• incorporated couplers have fairly large molecules in order to prevent the diffusion or substantial movement of such couplers within the particular hydrophilic colloid layer into which they were incorporated during the manufacture of the photographic element.
• diffusible' couplers are soluble in alkaline solutions which also usually contain one or more organic aromatic amino developing agents.
• diffusible couplers when diffusible couplers are used, their capability ofdiffusing into (and through) the emulsion layers of the photographic element being treated makes it possible for them to react (couple) with oxidized aromatic amino color developer(s) and thereby become effectively bound into the emulsion layer. In this situation. unreacted diffusible coupler can be readily removed from the photographic element via simply washing the element with water.
• Diffusible couplers that form yellow dyes have, to date, exhibited more of a need in this respect than have other types of color-forming couplers.
• couplers (and compositions containing them) of the present invention apparently result from the unique combination of substituents on the basic ketomethylene backbone structure of the coupler compounds encompassed by Formula I above.
• couplers having a. an aryloxy coupling of group attached through the ether linkage directly to the active carbon atom of the coupler and b. a branched alkyl group (such as R in structure I above) attached to one of the activating carbonyl groups in an acetanilide coupler.
• HY DROLYTIC STABILITY TEST As it was stated above, one of the valuable properties of the materials of the present invention relates to their surprisingly highresistance to hydrolysis under conditions which simulate end-use conditions; namely, in aqueoussolution at a buffered pH of 12.06 and at a temperature of 239C. Under such conditions, with the coupler being dissolved in the aqueous buffered solution at a concentration of coupler about 6.6 X 10' molar, many couplers have been found to degrade (hydrolyze) at varying rates of hydrolysis. The rates of hydrolysis are apparently unaffected by the presence or absence of color developing agent in the solution.
• compositionsof the-present invention comprise one or more p.-'phenylenedia mine type color developing agents.
• Such agents are well known an'dneed not be described in detail herein, since any phenylenediamine color developing-agent .can be'used.
• a preferred pphenylenediamine-type color developing agent is 4- amino-N-ethyl-N-(2-methoxyethyl)-m-toluidine, di-ptoluenesulfonate salt.
• the coupler compounds of structure I can be used successfully in combination with such color developing agents. The ratio of color develinthis test.
• the coupier/color developer compositions of this invention are preferably' b'lends of solid ,icr-ystalline or powdered materials whichb-lendscanreadily be dissolved in aqueous compositions in the preparation of color developer bziths:
• Such baths which contain yellow dye-forming 2'5 coupler dissolved therein, can then be used in the conventional manner during the yellow developer step in a multi-step process for manufacturing colored pho- EXAMPLE
• a conventional photographic element comprising a Data resulting fromqsubjeeting the processed film strips to spectrophotometric absorption tests were recorded.
• Couplers providing data for Table II were so-called fourequivalent-couplers, while those providing data for Table lIl were two-equivalent" couplers.
• Substituent groups appearing at the column headings in these Tables refer to the structural formula at the beginning of each table. 1
• Coupler Material O H O CO2CH2C6H5 A solution of 76.9 g of the amide (I) and phenol(ll) times with 100 ml water and then dried over M SO in 400 ml of acetonitrile containing 30.1 g. triethylam- 55 filtered, and concentrated in vacuum. The resulting ine was heated at reflux for 2 /2 hours. The solution was yellow syrup was dissolved in 200 ml methanol and then evaporated in vacuum. The resulting solid matecrystallized at room temperature. The dried crystalline rial was dissolved in 500 ml chloroform, extracted 3 product had a melting point of 92-95C.
• Step 2 O H O H2/Pd 1
• a solution of 51.4 g of the product from Step 1, above, in 300 ml ethyl acetate and 2.0 g of 10% palladium on carbon was shaken under 40 psi of hydrogen until hydrogen uptake ceased. Then the solution was warmed to completely dissolve the product. The resulting suspension was filtered to remove catalyst, and the filtrate was dried. The pale, pink solid material was recrystalized twice with methanol containing charcoal (for color improvement) to yield a product (Compound lV) having a melting point of l85l87.5C.
• a color developer composition comprising at least one organic aromatic primary amino developing agent and a yellow-dye-forming coupler material; the improvement which comprises using as said yellowdye-forming coupler material a compound having the structure:
• R is a branched alkyl group containing 3 to 6 carbon atoms; X is Cl or Br; Y is X, hydrogen or alkyl (l'to 8 carbon atoms); and A and B differ and are either H or COOM, wherein M is a photographically inactive cation or a methyl or ethyl group.

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)

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Citations (2)

• 1974
  • 1974-07-26 US US492116A patent/US3929484A/en not_active Expired - Lifetime
• 1975
  • 1975-02-11 CA CA219,819A patent/CA1041116A/en not_active Expired
  • 1975-03-04 JP JP2642975A patent/JPS559697B2/ja not_active Expired
  • 1975-03-07 IT IT21050/75A patent/IT1034108B/it active
  • 1975-03-07 CH CH294275A patent/CH593500A5/xx not_active IP Right Cessation
  • 1975-03-07 FR FR7507135A patent/FR2263537B1/fr not_active Expired

Patent Citations (2)

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