Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
  • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D257/04—Five-membered rings
• • 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
  • G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
  • G03C8/02—Photosensitive materials characterised by the image-forming section
  • G03C8/08—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic 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
  • Y10S430/156—Precursor compound
  • Y10S430/158—Development inhibitor releaser, DIR

Definitions

• This invention concerns inhibitor-releasing developers and more particularly photographic emulsions containing such developers.
• developing agents in the photographic emulsion. These developing agents can be activated to provide development of the latent image and in some instances to harden or tan the colloid containing the silver halide in the ex posed regions which will subsequently form relief images after the unhardened images have been removed.
• the presence of the developing agent in the photographic emulsion may have an adverse effect on the keeping qualities of the emulsion resulting in an overall hardening of the emulsion or fogging.
• the developing action carried on by the use of an alkaline agent which initiates development may result in fog or other adverse results. Therefore, it has been desirable to incorporate a development inhibitor agent along with the developer which would reduce fog and improve the keeping characteristics of the photographic emulsion.
• a development inhibitor agent would also result in inactivating the developer or keeping it in an inactive state until such time that it is needed for carrying out development following exposure.
• Hydroquinone has been combined with various materials in the prior art for use as developers or for in corporating in photographic emulsions. For instance, certain compounds of this type have been used wherein it is desired to eliminate and minimize the need for washing or stabilizing operations in liquid photographic baths subsequent to the formation of the silver image, for instance in the diffusion transfer systems, particularly where prints are desired from a silver halide emulsion which has been substantially underexposed in relation to its ASA exposure index.
• these prior art hydroquinone derivatives do not provide inhibitors at the site of development or produce the desired effect of reducing contrast with no loss of speed.
• One object of this invention is to provide inhibitorreleasing developers. Another object is to provide photographic emulsions containing inhibitor-releasing developers. A further object is to provide developer containing emulsions having reduced contrast and increased edge effects with little or no loss in effective speed. A further object is to provide a development inhibitor in chemical combination with a developing agent which releases the inhibitor at or near the site of development. A still further object is to provide aryl or alkyl mercaptotetrazole substituted hydroquinones. Other objects will be apparent from the following disclosure.
• hydroquinone developers which are useful in our invention are preferably prepared by reacting a p-benzoquinone with a mercaptotetrazole.
• the phenylmercaptotetrazole derivatives of hydroquinone are preferably incorporated in the photographic emulsion by forming a dispersion in a high boiling crystalloidal solvent of the type described in Jelley et al., U.S. Patent 2,322,027. These developers may be substituted in an amount of 5 to mol percent depending upon the particular compound and the desired decrease in contrast.
• X, Y and Z represent a hydrogen atom, alkyl groups (for example alkyl groups having about 1-20 carbon atoms, such as methyl, butyl, octyl, decyl, tridecyl, eicosyl, etc.), OH, amine, aryl groups (for example aryl groups such as phenyl, tolyl, xylyl, etc.), halogen, heterocyclic groups (for example heterocyclic groups such as tetrazolyl, thiazolyl, quinolinyl, etc.), or mercaptophenyltetrazole and R represents an aryl group (such as phenyl, tolyl, xylyl, etc.) or a lower alkyl group, (for example methyl, ethyl, propyl, butyl, amyl, etc.).
• X and Y are members of a carbocyclic ring.
• the substituents on the hydroquinone ring are not critical and may be the same or different.
• the substituted hydroquinone will be an active developer, However, the activity of the substituted hydroquinone will depend upon its desired use and may be negligible.
• the IRD hydroquinone developers useful in this invention may be prepared as shown by the following preparation of l-phenyl-5-tetrazolylthio)p-benzoquinone.
• Strips of a silver bromoiodide photographic emulsion coating were exposed on an intensity scale sensitometer and processed according to the procedure given in Example 1, except that only 10 mol percent of the hydroquinone in the check developer was replaced with each of the hydroquinones described as follows.
• Developer B As in Developer A, except:
• hydroquinone-phenyl mercapto tetrazole derivatives are compared to other heterocyclic mercaptanhydroquinones such as hydroquinone derivatives of mercapto benzothiazole, mercapto benzimidazole, mercapto thiazoline, mercapto pyridine and etc., similar advantages are obtained with the hydroquinone-phenyl mercapto tetrazole derivative as described in the comparative example given.
• EXAMPLE 4 A sample of silver bromoiodide film was exposed to X-ray using a knife edge to get a sharp edge.
• a formula containing 1 g./l. of hydroquinone, 5.2 g./l. of (1-phenyl-5-tetrazolylthio) hydroquinone, g./l. of sodium sulfite, 30 g./l. of sodium carbonate monohydrate, and 0.1 g./l. of potassium bromide at a pH of 11.5 fog was repressed adjacent to the exposed area. This type of effect in a negative is useful in producing enhanced sharpness in a positive print.
• EXAMPLE 6 Coatings 48810-A silver chlorobrornide photographic emulsion was coated on a cellulose acetate support at 300 mg. Ag/ft. and 692 mg. gel/ft.
• Example 1 Each of the above coatings was exposed on an Edgeton Germeshausen and Grier Mark V1 sensitometer and processed as in Example 1.
• EXAMPLE 10 In order to prepare a gelatin overcoat for a color negative, the following dispersion is prepared. A separate dis-- persion is prepared as a control without any hydroquinone derivative.
• Part A is slowly added to Part B with the aid of mechanical agitation.
• the solution obtained is then passed through a Caton-Gaulin laboratory colloid mill five times.
• the colloid mill is then rinsed and the dispersion is adjusted to a weight of 3775 g. chill set and stored in a refrigerator.
• a negative element was made in which the top layer of a basic color negative is prepared as follows:
• Parts I and 11 are then combined and diluted with distilled water to 22,700 ml.
• This solution is coated as the top layer of a basic color negative to yield a coverage of approximately mg. of gelatin per square foot and 40 mg. of the hydroquinone per square foot. This coating is compared to the control coating.
• the negatives After exposure on an intensity scale sensitometer the negatives are processed in an aqueous activator containing 3.5 percent hydroxyethyl cellulose, 4.5 percent NaOH and 2.0 percent benzotriazole, and the released dyes are transferred imagewise to a receiving sheet by lamination in the known manner.
• the receiving sheet is a paper support carrying a gelatino coating containing a mixture of poly-4-vinyl pyridine and l-phenyl-5-mercaptotetrazole.
• the IRD developer compounds of our invention can be incorporated in an ordinary photographic silver halide emulsion, or colloidal dispersion of a water-permeable hydrophilic colloid suitable for preparing an undercoat or an overcoat for such silver halide emulsion, by mixing a solution or dispersion of the developer compound with the silver halide emulsion, or dispersion of hydrophilic colloid, prior to coating.
• an IRD developer can be made up as an oil dispersion by stirring a solution of grams of the IRD developing agent into 40 grams of warm tricresylphosphate, and then mixing thi solu tion with 100 grams of a 10 percent aqueous gelatin solution containing 10 cos.
• 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 tricrcsylphosphate can be employed, including any of the crystalloidal compounds described in Jelley and Vittum US. Patent 2,322,027, issued June 15, 1943.
• the resulting colloidal dispersion can then be added to a photographic silver halide emulsion, or to a dispersion of a waterpermeable 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 IRD developing agents 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 IRD development agent 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 F.
• Particnlarly 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 removed by squeegeeing or water spraying. The photographic element can then be stabilized by conventional fixation or stabilization, such as by sodium thiosulfate.
• the concentration of the IRD developers 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 IRD developer is incorporated within the silver halide emulsion undergoing development, it may be desirable to use a somewhat different concentration than would be used if the IRD developer were incorporated in a layer contiguous to the photographic silver halide emulsion.
• a useful concentration of IRD developer 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.
• IRD developer For incorporation in a layer contiguous to the silver halide emulsion layer, somewhat larger concentrations of IRD developer can be tolerated without adverse effects.
• a particularly useful effect of our invention is that even when incorporated Within the silver halide emulsion, the IRD developers have little or no desensitizing effects. In many cases, this is not true where development-inhibitors or 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 halides developing-out emulsions, such as, silver-chloride, -chlorobromide, -chloroiodide, -chlorobromoiodide, -bromide and -bromoiodide emulsions.
• Any of the conventionally employed water-permeable hydrophilic colloids can be employed in the silver halide emulsions, or in layer contiguous thereto.
• Typical water-permeable hydrophilie colloids include gelatin, albumin, polyvinyl alcohols, agar agar, sodium alginate, hydrolyzed cellulose esters, hydrophilic polyvinyl copolymers, 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 Feb. 3, 1942; 2,288,226, issued June 30, 1942; 2,334,864, issued Nov. 23, 1943; or the thiopolymers as described in Graham et al., U.S. application Ser. No. 779,839, filed Dec. 12, 1958, now Patent No. 3,046,129; and Dann et al., US. application Serial No. 779,874, now Patent No. 3,046,134, filed Dec. 12, 1958.
• the emulsions may also be chemically sensitized with reducing agents 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 watersoluble salts (Lowe and Jones U.S. Patent 2,521,926).
• reducing agents 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 watersoluble 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. application Serial No. 319,613, all filed Nov. 8, 1952, now U.S. Patents 2,728,663, 2,728,664 and 2,728,665, respectively, granted Dec. 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 J an. 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, now abandoned, filed August 5, 1961, of P. H. Stewart, G. E. Fallesen and J. 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 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, 1-phenyl-3-pyrazolidone, l-p-tolyl- 3-pyrazolidone, 1-phenyl-5-methyl-3-pyrazolidone, l-acetamidoprenyl-3-pyrazolidone, 3-acetoxy-1-phenyl-3-pyrazolidone (Enol ester), Z-(pyridinium acetyl)-l-phenyl-3- pyrazolidone chloride, l-phenyl 4,4 dimethyl-3-pyrazolidone, l-phenyl 4 methyl-3-pyrazolidone, l-phenyl-Z- benzoyl-3-pyrazolidone, l-phenyl 2 lauroyl-3-pyrazolidone, 1-phenyl-2-ch
• 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 based on the IRD developing agent compound. Depending upon the particular auxiliary developing agent employed, larger or smaller quantities can be used.
• the IRD developers of our invention can be used in emulsions intended for use in diffusion transfer processes which utilize the undeveloped silver halide in the nonimage areas of the negative 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.
• diffusion transfer processes which utilize the undeveloped silver halide in the nonimage areas of the negative 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 Jan. 29, 1952; 2,698,236, issued Dec. 28, 1954, and 2,543,181, issued Feb. 27, 1951; and Yackel et al. U.S. Patent 3,020,155, issued Feb. 6, 1962.
• 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 sufficient to release water, which may be present in the support or in a separate layer in the photographic element. This water then dissolves the activator solution from the hydrophilic colloid layers and takes it into the photographic halide emulsion layer where development is effected.
• the elevated temperatures from about 150 C. are usually sufficient to effect development in this manner. If desired, additional moisture can be added by spraying steam upon the sensitive surface of the photographic element.
• 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 represented by the following general formula:
• X and Y represent a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to carbon atoms, OH, amine, an aryl group, a halogen atom, a heterocyclic group and members of a carbocyclic ring
• Z represents a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom and a heterocyclic group
• R represents a member selected from the class consisting of an aryl group and a lower alkyl group.
• a photographic element comprising a support and a photographic silver halide emulsion layer comprising a water-permeable hydrophilic colloid layer containing a compound represented by the following general formula:
• X and Y represent a member selected from the class consisting of a hydrogen atom, alkyl groups, having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom, a heterocyclic group and members of a carbocyclic ring
• Z represents a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom and a heterocyclic group
• R represents a member selected from the class consisting of an aryl group and a lower alkyl group.
• a photographic element comprising a paper support and a photographic silver halide emulsion layer comprising a water-permeable hydrophilic colloid layer containing a silver halide developer and a compound represented by the following general formula:
• X and Y represent a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom, a heterocyclic group and members of a carbocyclic ring
• Z represents a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom and a heterocyclic group
• R represents a member selected from the class consisting of an aryl group and a lower alkyl group.
• a photographic element comprising a support and a photographic silver halide emulsion layer comprising a water-permeable hydrophilic colloid layer containing a colloidal dispersion of a compound in a water-insoluble,
• X and Y represent a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom, a heterocyclic group and members of a carbocyclic n'ng
• Z represents a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom and a heterocyclic group
• R represents a member selected from the class consisting of an aryl group and a lower alkyl group.
• a photographic element comprising a support and a photographic silver halide emulsion layer comprising a water-permeable hydrophilic colloid layer containing a colloidal dispersion of .a compound in tricresylphosphate, said compound represented by the following general formula:
• X and Y represent a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom, a heterocyclic group, and members of a carbocyclic ring
• Z represents a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom and a heterocyclic group
• R represents a member selected from the class consisting of an aryl group and a lower alkyl group.
• a photographic element comprising a support and a photographic silver halide gelatino emulsion layer containing a compound represented by the following general formula:
• a photographic element comprising a support and a photographic untanned silver halide gelatino emulsion layer containing a compound represented by the following general formula:
• X and Y represent a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, and aryl group, a halogen atom, a heterocyclic group and members of a carbocyclic ring
• Z represents a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group and a halogen atom, a heterocyclic group
• R represents a member selected from the class consisting of an aryl group and a lower alkyl group.
• a photographic element as defined is claim 2 wherein said compound is 2-methyl-5-(l'-phenyl-5'-tetrazolylthio)hydroquinone.
• a photographic element as defined in claim 2 wherein said compound is (l-phenyl-S-tetrazolylthio)hydroquinone.
• a photographic element as defined in claim 2 wherein said compound is 2-n-pentadecyl-X-(l-phenyl-S- tetr-azolythio)hydroquinone.
• 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 compound represented by the following general formula:
• X and Y represent a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom, a heterocyclic group and members of a carbocyclic ring
• Z represents a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom and a heterocyc'lic group
• R represents a member selected from the class consisting of an aryl group and a lower alkyl group.
• a photographic element comprising a flexible support having thereon a photographic silver halide emulsion layer and integral with said photographic element a waterpermeable hydrophilic colloid layer containing a compound represented by the following general formula:
• R represents a member selected from the class consisting of an aryl group and a lower alkyl group.
• X and Y represent a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom, a heterocyclic group and members of a carbocyelic ring
• Z represents a member selected from the class consisting of a hydro-genatom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom and a heterocyclic group
• R represents a member selected from the class consisting of an aryl group and a lower alkyl group.
• a silver halide photographic developer solution containing .a silver halide developer and a compound rep resented by the following general formula:
• I N-N NN Y Z wherein X and Y represent a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom, a heterocyclic group and members of a carbocyclic ring, Z represents a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom and a heterocyclic group and R represents a member selected from the class consisting of an aryl group and a lower alkyl group.
• a process for forming a visible photographic image comprising developing an exposedv 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 represented by the following general formula:
• X and Y represent a member selected from the class consisting of a hydrogen. atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom, a heterocyclic group and members of a carbocyclic ring
• Z represents a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom and a heterocyclic group
• R represents a member selected from the class consisting of an aryl group and a lower alkyl group by inbibing throughout said photographic silver halide emulsion layer an aqueous alkaline solution containing sutllcient alkali to give a pH of at least about 9.0.
• a process for forming a visible photographic image comprising developing an exposed photographic element comprising a support having thereon a photographic silver halide gela-tino emulsion layer containing a silver halide developer and a compound selected from the class of compounds represented by the following general formula:
• X and Y represent a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom, a heterocyclic group and members of a carbocyclic ring
• Z represents a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom and a heterocyclic group
• R represents a member selected from the class consisting of an aryl group and a lower alkyl group, by imbibing throughout said photographic silver halide emulsion layer an aqueous alkaline solution containing sufiicient alkali to give a pH of at least about 9.0.
• a process for forming a visible photographic image comprising developing an exposed 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 formula:
• X and Y represent a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom, a heterocyclic group and members of a carbocyclic ring
• Z represents a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom and a heterocyclic group
• R represents .a member selected from the class consisting of an aryl group and a lower alkyl group by imbibing throughout said photographic silver halide emulsion layer an aqueous alkaline solution containing a silver halide developer.
• a process for forming a photoresist comprising exposing a photographic silver halide emulsion layer containing a tanning silver halide developer and a compound selected from the class of compounds represented by the following general formula:
• X and Y represent a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom, a heterocyclic group and members of a carbocyclic ring
• Z represents a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom and a heterocyclic group
• R represents a member selected from the class consisting of an aryl group and a lower alkyl group, developing in an alkaline bath, and removing the untanned areas in warm Water.
• a process for forming a visible photographic image comprising developing an exposed photographic element comprising a support and a photographic silver halide emulsion layer by imbibing throughout said emulsion a silver halide developer solution containing a compound selected from the class of compounds represented by the following general formula:
• X and Y represent a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom, .a heterocyclic group and members of a carbocyclic ring
• Z represents a member selected from the class consisting of a hydrogen atom, alkyl groups having about 1 to 20 carbon atoms, OH, amine, an aryl group, a halogen atom and a heterocyclic group
• R represents a member selected from the class consisting of an aryl group and a lower alkyl group.

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• 1963
  • 1963-02-28 US US261835A patent/US3379529A/en not_active Expired - Lifetime
• 1964
  • 1964-02-20 DE DE1447632A patent/DE1447632C3/de not_active Expired
  • 1964-02-26 BE BE644382A patent/BE644382A/xx unknown
  • 1964-02-27 GB GB8163/64A patent/GB1058606A/en not_active Expired

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