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
  • 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
  • G03C1/35—Antiplumming agents, i.e. antibronzing agents; Toners
  • G03C1/355—Organic derivatives of bivalent sulfur, selenium or tellurium
• • 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
  • Y10S430/13—Antibronze agent or process

Definitions

• Y represents a member selected from the group consisting of ureidogroups, substituted ureido groups, and nitrogen-containing hetero.-; cyclic groups'having from five to six atoms inv the heterocyclic ring.
• X may represent a carbon chain suchas alkylene, e. g. meth-. ylene, ethylene, trimethylene, or the like, or substituted alkylene, or methine, or polymethine, or ahetero-carbon chain, or a group comprising a carbocyclic component, e. g.
• Z represents the non-metallic atoms necessary to complete a heterccyclic nucleus con: taining from five to'six atoms in the heterocyclic ring.
• Z represents the non-metallic atoms necessary to complete a heterccyclic nucleus con: taining from five to'six atoms in the heterocyclic ring.
• These substances of the invention are added preferably to the emulsion layer or layers but they are also effective, when of the requisite solubility, if added to the developing solution or to other layers carried on the sensitive emulsion support such as the backing layer or supercoat.
• the sensitive layer may he bathedin asol h tion of the agent after exposure but prior to development.
• the substance is added to the emulsion layer preferably in amountscorresponding to 1-10 g. for every 127 g. ofsilver orto a developer at the rate of 0.2-2.0 g./litre. Higherconcentrations of the agent may be used without increasing the efiect.
• Thecompounds'according to the invention are also'valuable for preventing or reducing the overa'll'silver deposit termed fog which is frequently obtained on developing silver halide emulsion.
• concentrations as low as 0.10 gram per 127 grams of silver may be used, butat these low concentrations there is very littleefiect on'the colour of the image.
• the compounds are very effective as antiplumming agentswhen used in any of the ways previously-described or by bathing-the developed imagein a solution of" the compound after fixation.
• a suitable bath is, for example, an aqueous solution containing from 0.2 to 2.0 grams/litre of the anti-plumming agent.
• Example III S :S -trz'methyIene-bisthz'urom'um bromide I c. c.) and ethyl alcohol (50 c. c.), are refluxed Although in the specification we have described that our invention is by no means'llmited to such baths.
• processing we include any treatment given to the photographic material after exposure and up to the production of the final washed image and, in the case, oi ,printsespecially, including the final, hot-glazing treatment
• the agent is preferably added in the developingsolutions (when .no.t ..alread;y present .in the photographic n aterial) itmay be-added in the fixing bath or prior to washing since sufiicient-oithe compound willbaadsorbed to the-silver grains :to giverthedesir dan ieplumming effect dur ng.hot glazing of theprint.
• Que-invention is illustrated ,by the, following xamples of -eomp unds-w c m y be used v t gether with their methodsof preparation and use:
• Example IV'.-2 2 methylenethio-bis-dihydro Ethylenethiourea (2 thiotetrahydroiminazole) (Schacht, "Arch. dervPharm.,;l89.7, 235, 442 Klut,
• Example VIII.--2 :2'-trimethylenethio-bis- (4- methyliminazole) dihydrobromide a white 2 thio 4 methyltetrahydrominazole (3.5 g.) 1:3-dibromopropane (1.55 c. c.) and ethyl alcohol (25 c. 0.) were refluxed for 2 hours.
• ether was added to precipitate a thick oil which slowly crystallized.
• the ether-alcohol was decanted, the crystals washed with cold alcohol and dissolved in boiling ethyl alcohol.
• the slow addition of ether gave colourless needles of the salt, M. P. 177.
• Example IX.-D isodium 2:2'-et hylenethio bis- (4-amino-6-hydroxypyrimidi1re) C-SQHr-CHr-SC BrHgN NHzBr
• Ethylthiourea (5.2 g.), ethylene v dibromide (2.5 c. c.) and ethyl alcohol (20 c. 0.) were re.- fluxed for 1 hour.
• Dry ether was slowly added with shaking to give a mass of white crystals. They were collected, washed with alcohol-ether (1 :2) then with ether.
• M. P, 92" They are very hydroscopic. p
• Example XVIII.-.2 :z etnyzenemiois- (5 -tlliol- Triethylthiourea (8.0 g.), ethylene dibromide (2.5 c. c.) and ethyl alcohol (20 c. 0.) were refiuxed for 2 hours, chilled and the salt precipitated as an oil with dry ether.
• the ether was decanted and the process repeated shaking vigorously after each addition.
• the thick oil so obtained crystallized slowly on standing under ether. It was collected, drained well, dissolved in ethyl alcohol and reprecipitated with ether. It formed white needles, M. P. 130-132".
• Example XV.-S:S-ethylenethi0-bis-(l-methyldihydroiminazole) di-p-toluenesulphorvate on warming 2:2'-ethylenethio-bis-dihydroiminazole (1 mol.) with methyl p-toluenesulphonate (2 mol.) on the steam bath a vigorous reaction ensued and a thick oil remained; This is completely water soluble and is believed to have the above constitution.
• Example XVII .-4:4-ethylenethio bis (4:6-di- 2:4:6-trithio-1:3zfi-thiodiazine (0.97 g.) and ethylene dibromide (0.21 c. 0.) were dissolved in ethyl alcohol (l0 c. c.) and refluxed'for 1 hour during which fine white crystals, were formed. They were filtered oil, and recrystallized from 1 :3 :4-thiodia'zole) 2:5-dithiol-1:3:4-thiodiazole (3.0 g.) was dissolved in ethyl alcohol (15 0'. c.)..and-.ethylene di- 7 bromide (0.860. c.) added. After refluxing for hours, during which fine white crystals appeared;-'the mixture was cooled and filtered. The solid was "recrystallized from aqueous alcohol as white prisms M.iP. 254.
• Example D The addition of 1 g. of the compound of Example II per litre of normal metolhydroquinone developer when developing the fine grained positive emulsion, as used in Examples A and '3, gave blacks only faintly brown, compared with the pronounced olive brown tones normally obtained.
• Example F.5 g. of the compound of Example IV added to 5 litres of the-fine grained positive emulsion produced very strong blue-black effect.
• Example H.5 g. of the compound of Example VI added to 5 litres of the same emulsion reduced X added to 5 litres of the emulsion used above gave almost neutral blacks on development; after incubation for. 3 days at 50'C.the blacks obtained were slightly bluish.
• Example N .5 g. of the compound of Example;
• Example P.-''5 g'. ofthe compoundof Example XV added to 5 litresof thesame emulsion gave strong blue-black tones
• Example Q 701 A silver chloro+bromide emulsion coated on paper was exposed to a step wedge, developed, and fixed.
• Example T.- A highspeed panchromatic emulsion was coated: (a) as such with the usual hardener; (b) as (a) but with the addition of 0.25 g. of the compound of Example I! per 5 litres of emulsion containing the equivalent of 200 g. silver nitrate. On forced development or after incubation the coating (a) showed a much higher fog than did (b) Other agents'such as those of Examples II, V, VI, VII, X, XI, XII, etc., added to the emulsion at the samerate also showed pronounced antifog ⁇ ging and stabilizing properties.
• Example U.A silver chlorid emulsion was divided and one part coatedon paper. The other part was melted and to an amount of the emulsion containing the equivalent of 200 g. silver nitrate was added 8 g. of the compound of Example II and the emulsion coated.
• stripsv of the two coatings were hot glazed. Those strips containing the agent showed a much blacker and high maximum density than the strips coated with the untreated emulsion.
• Example V Substitution of the same quantity of the compound of Example XVII for the compound of Example II in the experiments of Example U gave similar results. 7
• Example W 'Substitutionof the same quantity of the compound of Example XVIII for the compound of Example II in the experiments of Example V gave'similar results and the increase in maximum density was particularly good in this case. l
• Method of producing developed photo-- graphic images of improved quality from a photographic material having a sensitive silverhalide emulsion layer comprising developing the said material in the presence of a compound selected from the grouprepresented by the following general formulae:
• X represents a divalent organic group selected from the class consisting of v,alkylene and where X represents a divalent organic group selected from the class. consisting of alkylene and xylylene
• R, R and R" each represent groups selected from the class containing hydrogen, alkyl, aryl and arylkyl groups
• Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing from five to six atoms in the heterocyclic ring.
• Method of producing developed photographic images of improved quality from a photographic material having a sensitive silver halide emulsion layer comprising developing the said material in a developing solution containing a compound selected from the group represented by the following general formulae:
• X represents a divalent organic group selected from the class consisting of alkylene and xylylene
• R, R and R" each represent groups selected from the class containing hydrogen, alkyl, aryl and arylkyl groups
• Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing from five to six atoms in the heterocyclic ring.
• a photographic material comprising a support having thereon a light-sensitive layer and a layer containing a compound selected from the group represented by the following general formulae:
• X represents a divalent organic group selected from the class consisting of alkylene and xylylene
• R, R and R" each represent groups selected from the class containing hydrogen, alkyl, aryl and arylkyl groups
• Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing from five to six atoms in the heterocyclic ring.
• Agphotographic material comprising a sensi-- tive' silver halide emulsion layer containing a compound selected from the groups, represented by the following general formulae:
• X represents a divalent organic group selected from the class consisting of alkylene and xylylene
• R, R and R" each represent groups selected from'the class containing hydrogen, alkyl, aryl and-arylkyl groups
• Z represents the non-metallic atoms necessary to complete a heterocyclic *nucleus containing from five to six atoms in the heterocyclic ring.
• a photographic material comprising a sensitive silver halide emulsion layer containing the quaternary salt of a compound having the following formula:
• a photographic.- material comprising a sensitive silver halide emulsion layer containing the quaternary salt'of atcompound having the following formula:
• X represents an alkylene group. and R represents an .alkyl group.

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

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Citations (3)

• 0
  • FR FR964821D patent/FR964821A/fr not_active Expired
  • BE BE476657D patent/BE476657A/xx unknown
• 1946
  • 1946-04-05 GB GB10574/46A patent/GB616822A/en not_active Expired
• 1947
  • 1947-03-27 US US737710A patent/US2514650A/en not_active Expired - Lifetime

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