Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
  • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
  • C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
  • C07C49/727—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
  • C07C49/737—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system having three rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
  • C07C49/613—Unsaturated compounds containing a keto groups being part of a ring polycyclic
  • C07C49/617—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system
  • C07C49/623—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
  • C07C49/637—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing ten carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
  • C07C49/613—Unsaturated compounds containing a keto groups being part of a ring polycyclic
  • C07C49/617—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system
  • C07C49/643—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having three rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
  • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
  • C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
  • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
  • C07C49/693—Unsaturated compounds containing a keto groups being part of a ring containing halogen polycyclic
• • 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
  • G03C1/00—Photosensitive materials
  • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
  • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
  • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
• • 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
  • G03C1/00—Photosensitive materials
  • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
  • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
  • G03C1/42—Developers or their precursors
• • 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
  • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
  • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
  • G03C5/29—Development processes or agents therefor
  • G03C5/30—Developers
• • 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
  • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
  • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
  • G03C5/29—Development processes or agents therefor
  • G03C5/30—Developers
  • G03C5/3021—Developers with oxydisable hydroxyl or amine groups linked to an aromatic ring
• • 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
  • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
  • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
  • G03C5/29—Development processes or agents therefor
  • G03C5/315—Tanning development

Definitions

• This invention relates to light-sensitive photographic silver halide emulsions and more particularly to photographic silver halide emulsions which contain a photographically compatible precursor of a silver halide developing agent.
• the difference in absorption between the gelatin relief areas and the background can be used for imbibition of dye solutions for transfer to mordanted receiving sheets;
• the relief can be used in photochemical processes, such as topography or gravure;
• the difference in ink-water receptivity of the gelatin relief and the hydrophobic support can be employed in lithographic printing.
• the relief can be transferred to other support, such as silk screen for stencil printing and the like.
• the difference in the ink receptivity of the hardened and unhardened areas can be employed directly without wash ofi as in the lithographic printing process of US.
• the exposed photographic element comprising a support having at least one gelatino-silver-halide emulsion layer thereon, is immersed in a developing bath containing a silver halide photographic developing agent.
• the developing bath is normally maintained as a separate processing bath and with continuous use, the bath usually becomes less eflicient so that special techniques and replenishments are normally required to maintain optimum processing efficiency.
• the developing baths of the prior art normally contain a developing agent, a preservative, such as sodium sulfite, and alkali to activate the developing agent, and may also contain other materials, such as sodium bromide (restrainer), antifoggants, etc.
• the tanning silver halide developing agent directly in the sensitive emulsion.
• this is convenient, it is frequently disadvantageous because the tanning developing agent in exposure to a silver image in. hardened gelatin against a background of residual silver halide in unhardened waterdispersible gelatin by incorporating the tanning develop ing agent in the form of a precursor, which is compatible with silver halide, with the other normal constituents of silver halide gelatin emulsion layers and inert to atmospheric oxygen, but which liberates the active tanning photographic developing agent on treatment with an alkaline solution having a pH of at least 8.5.
• Another object is to provide silver halide photographic materials which have the precursor substances incorporated in the emulsion layers, or layers adjacent thereto.
• a further object is to provide developing agent precursors for the tanning development of the emulsion layers.
• Another object is to provide developing agent precursors which on incorporation into silver halide emulsion layers exert a desirable antifoggant action on the silver halide.
• Still another object is to provide a method of processing the emulsion layers of the invention. 4
• the developing agent precursors (Diels-Alder adducts) of our invention are illustrated by the following general formula:
• R and R represent a hydrogen atom, an alkyl group (for example, alkyl groups containing about 1 to 20 carbon atoms, such as methyl, propyl, amyl, decyl, tridecyl, eicosyl, etc.), an aryl group (for example, an aryl group such as phenyl, tolyl, xylyl, etc.), hydroxy, a sulfonic acid group, halogen, amino group (for example, amino groups such as NH NHR or NR in which R is a lower alkyl group), or a substituted thio group (for example, such as SY wherein Y represents an isocyclic group (for example, an isocyclic group such as phenyl, naphthyl, etc.), or a heterocyclic group (for example a heterocyclic group such as tetrazolyl, a thiazolyl, a quinolinyl, etc.); R R R and R represent a
• naphthoquinone 4 (9) 2-t-butyl-5,8-e-thano-4a,5,8,8a-tetrahydro-1,4-
• naphthoquinone CH H2 12 5,6,7,8,9,9-hexachl0ro-5,8-methano-4a,5,8,8a-
• tetraehydro-1,4-naphthoquinone The preparation of these adducts is well known. They are generally formed by the interaction between a quinone such as p-benzoquinone, toluquinone, 1,4-naphthoqu-inone, 2- (t butyl)-p-benzoquinone, t-butyl-p-benzoquinone, pxyloquinone, etc. and a diene, such as cyclopentadiene, cyclohexadiene, c: phellandrene, dimethylbutadiene, hexachlorocyclopentadiene, etc.
• quinone such as p-benzoquinone, toluquinone, 1,4-naphthoqu-inone, 2- (t butyl)-p-benzoquinone, t-butyl-p-benzoquinone, pxylo
• Compound 1 was prepared as follows:
• Single layer coatings of a medium speed gelatin-silver bromoiodide photographic emulsion were prepared which contained 725 mg./ft. of silver, 1200 n1g./ft. of gelatin, and the developer precursors respectively as shown in Table II below. The concentrations of the precursors used in the respective coatings are given in this table.
• a control i.e. one containing no developer precursor
• containing the same level of silver and gelatin as those described above was also prepared;
• the compounds of our invention can be incorporated into emulsion layers and generally causeno deleterious efiect on the elfective speed of the silver halide emulsion.
• the coatings containing the respective compounds exhibit improved stability on keeping relative to that of the control.
• the acetonitrile is used in the above activator solutions to aid in dissolving the experimental developer agents.
• a developer precursor can be made up as an oil dispersion by stirring a solution of 10 grams of the developing agent precursor into 40 grams of warm tricresylphosphate, and then mixing this solution with 100 grams of a 10 percent aqueous gelatin solution containing 10 cc. of a percent aqueous solution of an alkylnaphthylene sodium sulfonate wetting agent. The resulting dispersion can then be homogenized by passing for 5 times through a colloid mill to produce a homogeneous colloid dispersion.
• Solvents other than tricresylphosphate can be employed, including any of the crystalloidal compounds described in Jelley and Vitt-ume U.S. Patent 2,322,027, issued June 15, 1943.
• the resulting colloidal dispersion can then be added to an ordinary silver halide emulsion, or a dispersion of a water-permeable hydrophilic colloid, adapted for preparation of an undercoat or overcoat for such silver halide emulsion.
• the oil dispersion can be dried for storage purposes and then be reconstituted for use by merely mixing with water.
• the developing agent precursors of our invention can be adapted for addition to a liquid silver halide emulsion or colloidal dispersion by other means as well. Suitable methods will depend largely upon the solubility characteristics, particularly in water or polar solvents, of the particular precursors in question.
• Suitable supports comprise any of the well known supporting materials, such as cellulose ester film base (e.g., cellulose acetate, cellulose nitrate, cellulose acetate butyrate, cellulose acetate propionate, etc.), polyethylene, polypropylene, polystyrene, polyethylene terephthalate and other polyesters, paper, polycarbonates, etc.
• cellulose ester film base e.g., cellulose acetate, cellulose nitrate, cellulose acetate butyrate, cellulose acetate propionate, etc.
• polyethylene polypropylene
• polystyrene polyethylene terephthalate
• other polyesters paper, polycarbonates, etc.
• the photographic elements of our invention comprising a photographic development precursor either in the photographic silver halide emulsion layer, or layer contiguous thereto, or both, can then be exposed to an original or negative and developed by merely treating the exposed emulsion layer with an alkaline activator bath.
• Typical activator baths comprise, for example, an aqueous solution of an alkaline material, such as sodium carbonate, sodium hydroxide, potassium carbonate, potassium hydroxide, mixtures of sodium hydroxide and sodium sulfite, etc.
• Suitable baths can comprise, for example an aqueous solution containing about 1 percent sodium hydroxide and 5 percent sodium sulfite.
• a bath of the latter type is quite suitable for developing an exposed emulsion 'layer in about 30 seconds when the activator bath is at about 68 F.
• Modifications can easily be made in the activator baths without departing from the spirit and scope of the invention.
• an aqueous solution comprising about 4 percent of sodium carbonate and 5 percent of sodium sulfite produces development in about 30 seconds at 68 F.
• Another aqueous activator solution comprising 2 percent sodium hydroxide and 5 percent sodium sulfite produces useful photographic images in a few seconds when heated at 130 F.
• Particularly useful activator solutions have a pH of at least about 9.0 and preferably of at least about 10.5.
• the activator solutions of the present invention can be applied to an exposed photographic element in any number of known ways, such as by dipping, spraying, or other suitable surface applications. If desired, a thickener can be added to the activator solution to increase the viscosity of the composition and make it more adaptable for continuous processing. Viscous compositions can then be 10 removed by squeegeeing or water spraying. The photographic element can then be stabilized by conventional fixation or stabilization, such as by sodium thiosulfate.
• concentration of the precursors used in our invention will vary, depending upon the particular chemical compound involved and the location of the compound within the photographic element. That is, if the precursor is incorporated within the silver halide emulsion undergoing development, it may be desirable to use a somewhat dilferent concentration than would be used if the precursor were incorporated in a layer contiguous to the photographic silver halide emulsion.
• a useful concentration of precursor for incorporation in the emulsion is from about 0.01 to 4.0 moles per mole of silver halide.
• a particularly useful range is from about 0.1 to 2.0 moles per mole of silver halide, with especially useful results being obtained within the range of about 0.4 to 1.0 mole per mole of silver halide.
• a particularly useful eifect of our invention is that even when incorporated within the silver halide emulsion, the precursors have little or no desensitizing effects. In many cases, thi is not true Where developing agents, per se, are incorporated within the silver halide emulsion layers.
• Photographic silver halide emulsions useful in our invention comprise any of the ordinarily employed silver halide developing out emulsions, such as, silver-chloride, -chlorobromide, -chloroiodide, -chlorobromoiodide, -bromide and -brornoiodide developing-out emulsions.
• Any of the conventionally employed water-permeable hydrophilic colloids can be employed in the silver halide emulsions, or in layer contiguous thereto.
• Typical Waterpermeable hydrophilic colloids include gelatin, albumin, polyvinyl alcohol, agar agar, sodium alginate, hydrolyzed cellulose esters, hydrophilic polyvinyl copo'lymers, etc.
• Photographic silver halide emulsions useful in our invention can also contain such addenda as chemical sensitizers, e.g., sulfur sensitizers (e.g., allyl thiocarbamate, thiourea, allyl isothiocyanate, cystine, etc.), various gold compounds (e.g., potassium chloroaurate, auric trichloride, etc.).
• chemical sensitizers e.g., sulfur sensitizers (e.g., allyl thiocarbamate, thiourea, allyl isothiocyanate, cystine, etc.), various gold compounds (e.g., potassium chloroaurate, auric trichloride, etc.).
• sulfur sensitizers e.g., allyl thiocarbamate, thiourea, allyl isothiocyanate, cystine, etc.
• gold compounds e.g., potassium chloroaurate, auric trichloride,
• Photographic silver halide emulsions useful in our invention can also be sensitized by other means, such as by alkylene oxide polymers, many of which are well known to those skilled in the photographic art.
• alkylene oxide polymers include those of U.S. Patents 2,423,549 and 2,441,389.
• the emulsions of the invention can also contain speedincreasing compounds of the quaternary ammonium type as described in U.S. Patents 2,271,623, issued February 3, 1942; 2,288,226, issued June 30, 1942; 2,334,864, issued November 23, 1943; or the thiopolymers as described in Graham et al., U.S. application Serial No. 779,839, filed December 12, 1958, now U.S. Patent No. 3,046,129; and Dann et al., U.S. application Serial No. 779,874, filed December 12, 1958, now U.S. Patent No. 3,046,134.
• the emulsions may also be chemically sensitized with reducing agent such as stannous salts (Carroll U.S. Patent 2,487,850), polyamines such as diethylene triamine (Lowe and Jones U.S. Patent 2,518,698), polyamines such as spermine, (Lowe and Allen U.S. Patent 2,521,925), or bis-(B-aminoethyl) sulfide and its water-soluble salts (Lowe and Jones U.S. Patent 2,521,926)
• reducing agent such as stannous salts (Carroll U.S. Patent 2,487,850), polyamines such as diethylene triamine (Lowe and Jones U.S. Patent 2,518,698), polyamines such as spermine, (Lowe and Allen U.S. Patent 2,521,925), or bis-(B-aminoethyl) sulfide and its water-soluble salts (Lowe and Jones U.S. Patent 2,521,926)
• the emulsions may also be stabilized with the mercury compounds of Allen, Byers and Murray U.S. application Serial No. 319,611; Carroll and Murray U.S. application Serial No. 319,612; and Leubner and Murray U.S. ap plication Serial No. 319,613, all filed November 8, 1952, now U.S. Patents 2,728,663, 2,728,664, and 2,728,665, respectively, granted December 27, 1955.
• the addenda which we have described may be used in various kinds of photographic emulsions. In addition to being useful in X-ray and other nonoptically sensitized emulsions, they may also be used in orthochromatic, panchromatic, and infrared sensitive emulsions. They may be added to the emulsion before or after any sensitizing dyes which are used.
• the agents may be used in emulsions intended for color photography, for example, emulsions containing color-forming couplers or emulsions to be developed by solutions containing couplers or other color-generating materials, emulsions of the mixed-packet type, such as described in Godowsky, U.S. Patent 2,698,- 794, issued January 9, 1955; or emulsions of the mixed grain type, such as described in Carroll and Hanson U.S. Patent 2,592,243.
• auxiliary developing agents include those described in the copending application Serial No. 134,014, filed August 5, 1961, and now abandoned, of P. H. Stewart, G. E. Fallesen and I. W. Reeves, Jr.
• Typical auxiliary developing agents described in this application include 3-pyrazolidone compounds containing an alkyl (e.g., methyl, ethyl, etc.) or aryl substituent (e.g., phenyl, p-tolyl, etc.).
• pyrazolidone developing agents can contain an I acyl or acyloxy substituent which can be hydrolyzed from the 3-pyrazolidone compound by treatment with the above activator solutions to produce the desired auxiliary developing compound.
• Typical auxiliary developing agents include, for example,
• auxiliary developing agents can be varied and, of course, no auxiliary developing agent need be employed unless so desired.
• Useful concentrations of auxiliary developing agents vary from about 0.01 mole to 2.0 moles per mole of developing agent precursor compound. Depending upon the particular auxiliary developing agent employed, larger or smaller quantities can be used.
• the developer precursors of our invention can be used in emulsions intended for use in dilfusion transfer processes which utilized the undeveloped silver halide in the nonimage areas of thenegative to form a positive by dissolving the undeveloped silver halide and precipitating it on a receiving layer in close proximity to the original silver halide emulsion layer.
• Such processes are described in Rott U.S. Patent 2,352,014, issued June 20, 1944, and Land U.S. Patents 2,584,029, issued January 29, 1952; 2,698,236, issued December 28, 1954, and 2,543,181, issued February 27, 1951; and Yackel et a1.
• the activator solutions which are used in our invention are stable for extended periods of time and are not subject to-the harmful decomposition reactions so common to conventional photographic developing ;solutions when these developing solutions are stored for extended periods of time. No special precautions are required to prevent oxidation of the activator solutions since they are inherently quite stable.
• the activator solutions can be incorporated in a carrier, such as gelatin and coated in contact with the photographic silver halide emulsion layer which contains the development precursors of our invention. After exposure, the development can be effected merely by heating the photographic emulsion layer to a temperature sufiicient to release Water, which may be present in the support or in a separate layer in the photographic element.
• the elevated temperatures from about 150 C. are the elevated temperatures from about 150 C.
• a photographic element comprising a support and a photographic silver halide emulsion layer, and integral with said photographic element a water-permeable hydrophilic colloid layer containing a compound selected from the class of compounds represented by the following general formulas:
• ⁇ represents a member selected from the class consisting of a hydrogen on each of the 5 and 8 carbon atoms, a methyL ene attached to the 5 and 8 carbon atoms, an ethylene group attached to the 5 and 8 carbon atoms and methylene and ethylene groups substituted with a member selected from the class consisting of a halogen, an aryl group and lower alkyl groups, said methylene and ethylene groups attached to the five and eight carbon atoms.
• a photographic element comprising a support and a photographic water-permeable hydrophilic colloid silver halide emulsion layer containing a compound selected This Water then dissolves the activator solution from the hydrophilic colloid layers and from the class of compounds represented by the following general formulas:
• R and R represent a member selected from the class consisting of hydrogen, an alkyl group from 1 to 20 carbon atoms, an aryl group, hydroxy, a sulfonic acid group, halogen, amino and a substituted thio group SY, wherein Y represents a member selected from the class consisting of an isocyclic group and a heterocyclic group, wherein R R R and R represent a member selected from the class consisting of hydrogen, halogen, an aryl group, and a lower alkyl group; X represents a member selected from the class consisting of a hydrogen on each of the 5 and 8 carbon atoms, a.
• methylene attached to the 5 and 8 carbon atoms an ethylene group attached to the 5 and v8 carbon atoms and methylene and ethylene groups substituted with a member of the group selected from the class consisting of a halogen, an aryl group, and lower alkyl groups, said methylene and ethylene groups attached to the five and eight carbon atoms.
• a photographic element comprising a paper support and a photographic silver halide emulsion layer, and integral with said photographic element a water-permeable hydrophilic colloid layer containing a compund selected from the class of compounds represented by the following general formulas:
• R and R represent a member selected from the class consisting of hydrogen, an alkyl group from 1 to 20 carbon atoms, an aryl group, hydroxy, a sulfonic acid group, halogen, amino and av substituted thio group S-Y, wherein Y represents a member selected from the class consisting of an isocyclicv group and a heterocyclic group, wherein R R R and R represent a member selected from the class consisting of hydrogen, halogen,- an aryl group, and a lower alkyl group;
• X represents a member selected from the class consisting of a hydrogen on each of the S and 8 carbon atoms, a methylene attached to the 5 and 8 carbon atoms, an ethylene group attached to the 5 and 8 carbon atoms and methylene and ethylene groups substituted with a member of the group selected from the class consisting of a halogen, an aryl group, and lower alkyl groups, said methylene and ethylene groups attached to the five and
• -A photographic element comprising a support and a photographic silver halide emulsion layer, and integral with said photographic element, a colloidal dispersion of a compound in a water-insoluble, water-permeable crystalloidal solvent, said compound being selected from the class of compounds represented by the following general formulas:
• R and R represent a member selected from the class consisting of hydrogen, an alkyl group from 1 to 20 carbon atoms, an aryl group, hydroxy, a sulfonic acid group, halogen, amino and a substituted thio group SY, wherein Y represents a member selected from the class consisting of an isocyclic group and a heterocyclic group, wherein R R R and R represent a member selected from the class consisting of hydrogen, halogen, an aryl group, and a lower alkyl group; X represents a member selected from the class consisting of a hydrogen on each of the 5 and 8 carbon atoms, a methylene attached to the 5 and 8 carbon atoms, an ethylene group attached to the 5 and 8 carbon atoms and methylene and ethylene groups substituted with a member selected from the class consisting of a halogen, an aryl group, and lower alkyl groups, said methylene and ethylene groups attached to the five and eight carbon atoms.
• a photographic element according to claim 4 wherein said crystalloidal solvent is a high-boiling ester of a phenol.
• a photographic element according to claim 5 wherein said high-boiling ester is tricresylphosphate.
• a photographic element comprising a paper support and a photographic silver halide emulsion layer, and integral with said photographic element a water-permeable, hydrophilic colloid layer containing (a) a compound selected from the class of compounds represented by the following general formulas:
• R and R represent a member selected from the class consisting of hydrogen, an alkyl group from 1 to 20 carbon atoms, an aryl group, hydroxy, a sulfonic acid group, halogen, amino and a substituted thio group SY, wherein Y represents a member selected from the class consisting of an isocyclic group and a heterocyclic group, wherein R R R and R represent a member selected from the class consisting of hydrogen, halogen, an aryl group and a lower alkyl group; X represents a member selected from the class consisting of a hydrogen on each of the 5 and 8 carbon atoms, a methylene attached to the 5 and 8 carbon atoms, an ethylene group attached to the 5 and 8 carbon atoms and methyl ene and ethylene s substituted with a member of the group selected from the class consisting of a halogen, an aryl group, and lower alkyl groups, said methylene and ethylene groups attached to the five and eight carbon atom
• a photographic element comprising a flexible support and a photographic silver halide emulsion layer, and integral with said photographic element a waterpermeable hydrophilic colloid layer containing a compound selected from the class of compounds represented by the following general formulas:
• R and R represent a member selected from the class consisting of hydrogen, an alkyl group from 1 to 20 carbon atoms, an aryl group, hydroxy, a sulfonic acid II R5 I II R4 VB:
• Y represents a member selected from the class consisting of an isocyclic group and a heterocyclic group, wherein R R R and R represent a member selected from the class consisting of hydrogen, halogen, an aryl group, and a lower alkyl group
• X represents a member selected from the class consisting of a hydrogen on each of the 5 and 8 carbon atoms, a methylene attached to the 5 and 8 carbon atoms, an ethylene group attached to the 5 and 8 carbon atoms and methylene and ethylene groups substituted with a member of the group selected from the class consisting of a halogen, an aryl group, and lower alkyl groups, said methylene and ethylene groups attached to the five and eight carbon atoms.
• a photographic element comprising a support and a photographic silver halide gelatino emulsion layer containing a compound selected from the class of compounds represented by the following general formulas:
• R and R represent a member selected from the class consisting of hydrogen, an alkyl group from 1 to 20 carbon atoms, an aryl group, hydroxy, a sulfonic acid group, halogen, amino and a substituted thio radical S-Y, wherein Y represents a member selected from the class consisting of an isocyclic group and a heterocyclic group, wherein R R R and R represent a member selected from the class consisting of hydrogen, halogen, an aryl group, and a lower alkyl group; X represents a member selected from the class consisting of a hydrogen on each of the 5 and 8 carbon atoms, a methylene attached to the 5 and 8 carbon atoms, an ethylene group attached to the 5 and 8 carbon atoms and methylene and ethylene groups substituted with a member of the group selected from the class
• a photographic element comprising a support and a photographic silver halide untanned gelatino emulsion layer containing a compound selected from the class of conlrpounds represented by the following general formu as:
• R and R represent a member selected from the class consisting of hydrogen, an alkyl group from 1 to 20 carbon atoms, an aryl group, hydroxy, a sulfonic acid group, halogen, amino and a substituted thio group SY, wherein Y represents a member selected from the class consisting of an isocyclic group and a heterocyclic group, wherein R R R and R represent a member selected from the class consisting of hydrogen, halogen, an aryl group, and a lower alkyl group; X represents a member selected from the class consisting of a hydrogen on each of the 5 and 8 carbon atoms,
• R and R represent a member selected from the class consisting of hydrogen, an alkyl group from 1 to 20 carbon atoms, an aryl group, hydroxy, a sulfonic acid group, halogen, amino and a substituted thio group SY, wherein Y represents a member selected from the class consisting of an isocyclic group and a heterocyclic group, wherein R R R and R represent a member selected from the class consisting of hydrogen, halogen, an aryl group, and a lower alkyl group;
• a photographic element comprising a support and a photographic, water-permeable, hydrophilic, silver halide emulsion layer containing a compound selected from the class of compounds represented by the following general formula:
• Ra I0 R4 RUQU Q? Y I R; 0 R5 wherein R R R and R represent a member selected from the class consisting of hydrogen, halogen, an aryl group, and a lower alkyl group; X represents a member selected from the class consisting of a hydrogen on each of the 5 and 8 carbon atoms, a methylene attached to the 5 and 8 carbon atoms, an ethylene group attached to the 5 and 8 carbon atoms and methylene and ethylene groups substituted with a member of the group selected from the class consisting of a halogen, an arylgroup, and lower alkyl groups, said methylene and ethylene groups attached to the five and eight carbon atoms.
• a process for forming a visible photographic image comprising developing a photoexposed photographic element comprising a support and a photographic silver halide emulsion layer, and integral with said photographic element a water-permeable, hydrophilic colloid layer containing a compound selected from the class of compounds represented by the following general forwherein R and R represent a member selected from the class consisting of hydrogen, an alkyl group from 1 to 20 carbon atoms, an aryl group, hydroxy, a sulfonic acid group, halogen, amino and a substituted thio group SY, wherein Y represents a member selected from the class consisting of an isocyclic group and a heterocyclic group, wherein R R R and R represent a member selected from the class consisting of hydrogen, halogen, an aryl group and a lower alkyl group; X represents a member selected from the class consisting of a hydrogen on each of the 5 and 8 carbon atoms, a methylene attached to the 5 and 8 carbon atoms
• a process for forming a photoresist comprising exposing a photographic silver halide emulsion layer containing a compound selected from the class of compounds represented by the following general formulas:
• R and R represent a member selected from the class consisting of hydrogen, an alkyl group from 1 to 20 carbon atoms, an aryl group, hydroxy, a sulfonic acid group, halogen, amino and a substituted thio group --SY, wherein Y represents a member selected from the class consisting of an isocyclic group and a heterocyclic group, wherein R R R and R represent a member selected from the class consisting of hydrogen, halogen, an aryl group and a lower alkyl group; X represents a member selected from the class consisting of a hydrogen on each of the 5 and 8 carbon atoms, a methylene attached to the 5 and 8 carbon atoms, an ethylene group attached to the 5 and 8 carbon atoms and methylene and ethylene groups, said methylene and ethylene groups attached to the five and eight carbon atoms substituted with a member of the group selected from the class consisting of a halogen, an aryl group, and lower alkyl groups
• a photographic element as defined in claim 1 wherein said precursor is 6,7-dimethyl-4a,5,8,8a-tetrahydro-1,4-naphthoquinone.
• a photographic element as defined in claim 1 wherein said precursor is 5,8-methano-4a,5,8,8a-tetrahydro-1,4-naphthoquinone.
• a photographic element as defined in claim 1 wherein said precursor is 5,8-ethano-4a,5,8,Sa-tetrahydro-l,4-napl1thoquinone.
• a photographic element as defined in claim 1 wherein said precursor is 5,8-methano-2-methyl-4a,5,8, 8a-tetrahydro-1,4-naphthoquinone.
• a photographic element as defined in claim 1 wherein said precursor is 6,7-dimethyl-2-(1-phenyl5- tetrazolylthio -4a,5,8,8a-tetrahydro-1,4-naphthoquinone.
• Glafkides Photographic Chemistry, vol. 2, 1960, Fountain Press, London, p. 714.

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