Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
• • 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
  • G03C1/485—Direct positive emulsions
  • G03C1/48592—Positive image obtained by various effects other than photohole bleaching or internal image desensitisation, e.g. Sabatier, Clayden effect

Definitions

• This invention relates to light-sensitive photographic material and particularly to direct positive photographic material.
• Herschel-effect is known under the name' of Herschel-effect and may be used for obtaining a reversed image.
• .3 lt is'also known that desensitizing dyes y be added to the emulsion in order to increase the Herschel-effect.
• A a member selected from the group consisting of a single bond and NH, l
• B a member selected from the ,group consisting of aryl substituted with at least one:nitrogroup, arylene symmetrically substituted by at least one nitro;group', and arylene-SO -arylene substituted symmetrically by at least two nitro groups, the arylene and arylene-SO arylene groups constituting the centre of a symmetrical compound containing two dihydropyrimidine nuclei of one of the above tautomericformulae,"
• R a member selected from the group consisting of hydrogen, hydroxyl, alkyl, aralky'l and aryl,
• R a member selected from the group consisting of hydrogen, alkyl, aralkyl and aryl, V
• R a member selected from the group consisting of hydrogen, alkyl, aralkyl and aryl.
• the compounds may be incorporated in silver chloride, silver chloro-iodide or silver chloro-bromide emulsions.
• the optimum amount is between 25 mg. and 7.5 g. per equivalent of g. silver nitrate.
• the compounds according to the present invention may also be addedv to alayer which is adjacent to the emulsion. In general, the same, amounts per square metre are used.
• the emulsion is prefogged by light or chemical means, for example by formaldehyde or.stannous chloride. 7
• E mp 1 200 ml. of a 0.5%'solution methyl alcohol of the compound according to the formula are added to 1 kg. of a silver chloride emulsion containing the equivalent of 30 g. silver nitrate. Then this emulsion is coated on, a paper support and exposed to white light suflicient to'giving a density of at least 1.4 when developed in the following developer:
• the product of the formulaslast above given is prepared. as follows: 47.42 g. 2-4 dinitrophenylhydrazine are 'dissolved in 600 ml. dioxane, 39 g. 2-methyl-2-thiocyano-4-pentanone are added and the whole is refluxed for '3 hours. After-cooling, the solution is poured in water, the precipitate issucked off and washed with water-and cold ethyl. alcoliol; The precipitate is further washed with 500" ml. hydrochloric acid (2 N) whilst stirring, and, finally with water. The product melts, after recrystallization in acetic acid, at ;2-15 -21 7 C.
• Example 3 A gelatin upper layer 1.5% gelatin) whereto previously 100 ml. per litre of a 0.5% solution in diacetone aleohohofthe compound. according to the formula are added, is coated on a silver chloro-iodide emulsion 1% iodide) containing the equivalent of 20 g. silver nitrate per kg. The obtained photographic material is further treated as in Example 1.
• the product according to the formula last above given is prepared as follows: to a solution of 3.6 g. p-nitrophenyl-isothiocyanate in 20 ml. benzene, a solution of 1.68 g. beta-amino-butyric acid nitrile in 10 ml. benzene is added. After 30 minutes heating on the boiling water bath, the formed oil solidifies. After cooling, sucking off and recrystallizing in ethyl alcohol, a product according to the formula is obtained which melts at 13 8-139 C. 3.2 g. of product are refluxed for minutes in 30 strong hydrochloric acid. First the whole dissolves and after some time boiling a precipitate is formed. After-cooling, sucking off and recrystallizing in acetic acid, the desired product is obtained under the form offsmall white needles melting at 237--239 C.
• Example 5 Example 5 .50 ml. of a 0.5% solution in dioxane of the pound according to the formula are added to 1 kg. silver chloride emulsion containing the equivalent of 25 g. silver nitrate. Next, the emulsion is coated on a paper support. The photographic material obtained is further treated as in Example 1.
• the product according to the formula last above given is prepared as follows: 1.2 g. picryl hydrazine are dissolved in 60 ml. hydrochloric acid (5 N). Next, 0.78 g. 2-methyl-2-thiocyano-pentanone-(4) are added. The whole is boiled for 1 hour. After cooling, and standing overnight, the obtained product is sucked off, washed with water and recrystallized in acetic acid.
• Example 6 4 kg. of a silver chloro-bromide emulsion (10% bromide) containing the equivalent of 20 g. silver nitrate per kg. are heated to 40 C. and-brought at a pH of 8. Next, 8 ml. of an aqueous solution of formaldehyde (40%) are added and the emulsion is kept for 10 minutes at the same temperature. The pH is brought at 6 and 100 ml. of a 0.5% solution in diactone alcohol of the product according to the formula :are added. Then, the emulsion is coated on a film support. This chemically fogged emulsionis exposed to an a image through a Gevalor filter L 500.
• Example 1 The photographic material obtained is further treated as in Example 1.
• the product of the formula last above given is prepared as follows: 4.56 g. I-S-dinitro-4-6-hydrazino benzene are heated in 150 ml. water for 4 hours on the boiling water bath with 6.28 g. 2-methyl-2-thiocyano-4- pentanone. After, cooling and sucking off, the product obtained is washed with water, hydrochloric acid (2 N), water, ethyl alcohol and ether respectively. After recrystallization in acetic acid, the obtained product melts at 223-224 C.
• a direct positive silver halide photographic material comprising a silver halide emulsion layer and a gelatin layer adjacent thereto, the gelatin layer containing the product of the formula .6 2.
• a direct positive photographic material comprising CH (5 NO i NO: (I) 3 a MHGSOGNH a...
• a direct positive silver halide photographic material comprising a silver halide emulsion layer and a gelatin layer adjacent thereto, the gelatin layer containing the product of the formula 4.
• a direct positive photographic material comprising a silver halide emulsion containing the product of the 5.
• a direct, positive silver halide photographic material comprising a silver halide emulsion layer and a gelatin layer adjacent thereto, the gelatin layer containing the product of the-formula 6.
• a direct positive photographic material comprising a silver halide emulsion containing the product of the formula t it 11.75 7.
• a direct positive photographic material comprisihg a--silver halide emulsion containing the-producbof the formula 1 '9.
• a direct positive silver halide photographic material comprising a silver halide "emulsion layer and a gelatin layer adjacent thereto, the gelatin layer-containing the product of the formula 10.
• a direct positive silver halide photographic material comprising an unsensitive gelatin layer adjacent to the silver halide emulsion, said layer containing the product of the formula 11.
• a direct positive silver halide photographic material comprising arsilver halide emulsion layer and a gelatin layer adjacent thereto, at least one of said layers containing a compound selected from the group consisting of compounds corresponding to one of the tautomeric formulae:
• A represents a member: selected from the group consisting of a single bond and''NH-
• B represents an aryl radical substituted with at lea stone 'nitro group
• D represents a 'memberselcctedfrom the group consisting of an arylene radical s'ubstituted'with at least one nitro group, and an arylene-*SOy'arylene radical, each arylene group of which is substituted with-at least one nitro group
• R and R each represents a member selected from the group consisting of a hydroxyl radical and an alkyl radical
• R represents a member selected from the group consisting of a hydrogen atom, an alkyl radical, and an aryl radical.
• A represents a member selected from the group consisting of a single bond and NH-
• B represents an aryl radical substituted with at least one nitro group
• D represents a member selected from the group consisting of an arylene radical substituted with at least one nitro group, and an arylene-sO -arylene radical, each arylene group of which is substituted.
• R and R each represents a member selected from the group consisting of a hydroxyl radical and an alkyl radical
• R represents a member selected from the group consisting of a hydrogen atom, an alkyl radical, and an aryl radical.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)

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Citations (5)

• 0
  • BE BE543288D patent/BE543288A/xx unknown
• 1954
  • 1954-12-10 GB GB35797/54A patent/GB796873A/en not_active Expired
• 1955
  • 1955-12-06 US US551458A patent/US2901351A/en not_active Expired - Lifetime
  • 1955-12-09 DE DEG18553A patent/DE1019171B/de active Pending
  • 1955-12-09 FR FR1136718D patent/FR1136718A/fr not_active Expired

Patent Citations (5)

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