US2886437A - Photographic emulsions sensitized with alkylene oxide polymers and quaternary ammonium compounds - Google Patents

Photographic emulsions sensitized with alkylene oxide polymers and quaternary ammonium compounds Download PDF

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US2886437A
US2886437A US550495A US55049555A US2886437A US 2886437 A US2886437 A US 2886437A US 550495 A US550495 A US 550495A US 55049555 A US55049555 A US 55049555A US 2886437 A US2886437 A US 2886437A
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quaternary ammonium
emulsion
alkylene oxide
emulsions
compounds
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Douglas E Piper
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to FR1170223D priority patent/FR1170223A/fr
Priority to DEE13286A priority patent/DE1048146B/de
Priority to GB36640/56A priority patent/GB871801A/en
Priority to US746131A priority patent/US3017271A/en
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    • 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
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • 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
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • G03C1/043—Polyalkylene oxides; Polyalkylene sulfides; Polyalkylene selenides; Polyalkylene tellurides
    • 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
    • Y10S430/15—Lithographic emulsion

Definitions

  • silver halide emulsions may be chemically sensitized-with a variety of materials in order to increase the speed and generally the .gamma of the emulsion, as opposed to optical sensitization in which the 2,334,864 describe .the'chemical sensitization ofsilver halide emulsions with quaternary ammonium compounds.
  • emulsions which have been sensitized with alkylene oxide polymers not containing a quaternary ainmonium group, with and without optical sensitizing dyes, may be further increased by the use of quaternary ammonium compounds, and that this increase in sensitivity is'not accompanied by an increase in graininess.
  • polyalkylene oxide polymers and quaternary ammonium compounds can be used in combination in several ways to produce sensitivity increases, i.e., the compounds may be added-to the emulsion, the emulsion may be tr eated with the compounds before exposure and development, or
  • the quaternary ammonium silver halide sensitizing agents useful in the invention in conjunction with the alkylene oxide polymers include a wide variety of well known quaternary ammonium salts such as disclosed in U.S. Patents 2,288,226 and 2,271,623. 7
  • tetraalkyl quaternary ammonium salts having thegeneral formula in which X is an anion or acid radical, for example, halide, p-toluene sulfonate, alkyl sulfate or perchlorate, R, R R and R are alkyl groups of which at least one has a chain of seven or more atoms such as carbon atoms, carbon atoms plus oxygen atoms, sulfur atoms'or nitrogen atoms and ring systems, while the remaining R groups are alkyl such as methyl, ethyl, butyl, and benzyl as exemplified hereinafter.
  • X is an anion or acid radical, for example, halide, p-toluene sulfonate, alkyl sulfate or perchlorate
  • R, R R and R are alkyl groups of which at least one has a chain of seven or more atoms such as carbon atoms, carbon atoms plus
  • quaternary ammonium salts' has the general formula where X is as above and R represents a chain of at least seven atoms such asiabove; however; R may be an aralkyl group as small as fi-phenyl'ethyl, and Z represents the atoms necessary'to complete'a cyclic structure such as ⁇ a pyridyl, a-picolyl, piperidyl or m'orpholinyl nucleus.
  • R contains-a second quaternary nitrogen atom
  • a long chain may link the nitrogen atoms as in the bis-quaternary ammonium compounds tabulated hereinafterq i
  • Examples of the quaternary ammonium salt sensitizers are'given in the following table, the compound number for each salt being'th'at utilized in the emulsion examples hereinafter.
  • The. quantity of quaternary ammonium compound nature ofthe'quaternary. ammonium compound and with the nature-of the emulsion. Ordinarily, the most advantageous concentration has been found to be between about 50 mgs. and 5000 mgs. of the quaternary ammonium com- A pound per gram 'mole of silver halide in the emulsion,
  • any quaternary ammonium compound described herein is ordinarily fairly narrow and can best be determined by employing a series 'of'concentrations of the quaternary ammonium compound separately in several batches of the same emulsion and determining the sensitivity of the several batches before and after incorporation of the quaternary, ammonium compound, in the usual-manner which is,'of course, 'well'known to those skilled in the'art.
  • the alkylene oxide polymers used to sensitize the l emulsions may be of various types.
  • the alkylene oxides from which the polymers are derived contain from 2 to 4 carbonatoms, e.g.,.ethylene oxide, propylene. oxide and butylene oxide.
  • the preparation of polymers from these compounds is described in Ellis, The Chemistry of Synthetic Resins (1935 pages 990 to 994. These compounds are also referred to as polyalkylene glycols and their use as sensitizers for silver halide emulsions is described in U.S. Patents 2,423,549 and 2,441,389.
  • the alkylene oxide derivatives may beprepared by condensing an organic compound containing an active hydrogen atom with an alkylene oxide polymer, or by condensing the active hydrogen compound with the alkylene oxide during. the polymer-ization of the latter material.
  • Variousderivativesof alkylene oxides may also be used, to sensitize the emulsions, e.g.,condensation productsof alkylene oxide with organic compounds containing, an active hydrogen atom.
  • active hydrogen organic compounds i.e., compounds in which a hydrogenatom may be replaced by reaction of the compound with metallic sodium, methylmagnesium iodide, etc.
  • active hydrogen organic compounds include alcohols, amines, mercaptans, acids, amides, hydrocarbons such as acetylene, and compounds having the active hydrogen in a methylene group such as dibenzoylmethane.
  • condensation products of alkylene oxide with glycols such as those having from 8'- to 18 carbon atoms asdescribed in U.S. Patent 2,240,472 and British Patent 443,559 as well as condensation products of alkyl'ene oxideswith aliphatic alcohols, condensation products of alkylene oxides with aliphatic acids, e.g., lauric acid and glycine, condensation products of alkylene oxides with aliphatic amines or amides, e.g., glycine and lauryl amide, and condensation products of alkylene oxides with phenols, e.g., phenol.
  • the preparation of these condensation products is described in U.S. Patentl,970,578. Condensation products of alkylene oxides with hexitol ring dehydration products asdescribed in U.S. Patent 2,400,532 may also be employed.
  • the polyalkylene oxide or derivative of alkylene” oxide should have a molecular weight of at least 300'.
  • Condensation products of ethylene oxide' with long chain alcohols, acids, amines or amides should have a molecular weight of about 700;
  • the best results are obtained with the condensation products of ethylene oxide with long'chain compounds having achain length of 12 or more carbon atoms and with ethylene oxide polymers having a molecular weight of 1500 to 4000 or more.
  • optical sensitizing dyes When employing optically sensitized emulsions the optical sensitizing dyes are advantageously employed in about their optimum concentration which ordinarily lies between about 10 mgs. and 40 mgs. of optical sensitizing dye per liter of emulsion containing about 025 gram mole of silver halide although concentrations above or below the optimum concentration can be employed.
  • alkylene oxide derivatives used to sensitize the emulsions may be illustrated by the following specific examples, although our invent-ion is in no way limited to the use of these.
  • Polyethylene oxide nonyl phenol ether N methyP myri'stylamino polyethylene oxide N-rnethyL-n -dodecylaniino' polyethylene oxide optimum reaction temperature is 100 to 105 C.
  • product so obtained is. a. light amber colored waxy material; thecolor may be removed partially by treatment with charcoal in a suitable solvent.
  • This material is repres'ent'a'tive of anumber of condensation productsof ethylene oxide with secondary with gelatino-silver bromoiodide emulsions.
  • amines the alkyl' chain of which should contain at least nine carbon atoms and the polyethylene oxide chain should have a molecular weight of at least 500.
  • the preparation of silver halide emulsions involves;
  • sensitizing agents may be addedat any stage, preferably after the final digestion.
  • the emulsions maybe chemically sensitized by any of the accepted procedures, in addition to or in combination with the sensitizingv with alkylene. oxide polymers.
  • the emulsions may be digested with naturally active gelatin, or sulfur compounds may be added such as those described in Sheppard, U.S. Patents 1,574,944 and 1,623,499, and Sheppard. and Brigham, U.S. Patent 2,410,689.
  • the emulsions may also be treated with salts of the 9 noble metals such as ruthenium, rhodium, palladium,
  • iridium and platinum all of which belong, to group VIII of: the periodic table of. elements and have an atomic weight. greater than 1.00.
  • Representative compounds are ammoniumc'hloropalladate, p'otassiumchloroplatinate and sodium chloropalladite, which are used forsensitizing in amounts below that which produces any substantial fog inhibition, as described: in Smith an'd TriVelli, U.S. Patent. 2,4'48,0'60 and as: anti-foggants in higher amounts, as described in Trivelli and Smith, U.S. Patents 2,566,245 and 2,566,263.
  • the emulsions may also be chemically sensitized with gold salts as described in Waller and Dod'd, U.S. Patent 2,399,083, or stabilizedwith goldsalts as described in Damschroder', U.S. Patent 2,597,856, and Yutzy and Leer-- makers, UZS. Patent 2,597,915.
  • Suitable compounds are potassium chloroaurite, potassium aurithiocyanate, potassiur-n chloroaurate, auric trichloride and 2-aurosulfobenzothiazol'e methochloride.
  • the emulsions may also be chemically sensitized with reducing. agents such as stannous salts (Carroll, U.SL 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-(fl-aminoethyl) sulfide and its watersoluble salts (Lowe and Jones, U.S. Patent 2,521,926).
  • stannous salts Carroll, U.SL Patent 2,487,850
  • polyamines such as diethylene triamine
  • polyamines such as spermine
  • spermine Li.S. Patent 2,521,- 925 or bis-(fl-aminoethyl) sulfide and its watersoluble salts
  • the emulsions may alsobe 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 November 8, 1952, now U.S. Patents 2,728,663, 2,728,664 and 2,728,665 respectively, granted December 27, 1955.
  • stabilizing agents may be added to the emulsions containingthequaternary ammonium.
  • compounds and polyalkylene oxides such as cadmium chloride, cadmium.
  • the fog was found 5 to be increased somewhat on both fresh and incubated samples of the developed emulsion.
  • This fog was reduced to normal levels by use of an antifoggant such as an azaindene, for example, a 4-hydroxy-6-alkyl-1,3,3a,7- tetraazaindene specifically 4-hydroxy-6-methyl-l,3,3a,7- tetraazaindene and 5-carboxy 4 hydroxy-1,3,3a,7-tetraazaindene.
  • an antifoggant such as an azaindene, for example, a 4-hydroxy-6-alkyl-1,3,3a,7- tetraazaindene specifically 4-hydroxy-6-methyl-l,3,3a,7- tetraazaindene and 5-carboxy 4 hydroxy-1,3,3a,7-tetraazaindene.
  • polyalkylene oxides and derivatives thereof are identified as follows, the number following each name indicating the molecular weight of the particular polyethylene oxide chain.
  • Example 2 Addition ;of. the polyethylene oxide.
  • Example 1 Additional of the polyethylene oxide, quaternary ammonium salt and azaindene, to the emulsion before coating
  • Example 3 Additional of quaternary ammonium salt and 'tetraazaindene to' the emulsion and the polyethylene oxide to the developer 1 Emulsion is similarto that described in- Example, 1, containing the following addenda and exposed and processed as indicated: a
  • Example 4 Additional of the polyethylene oxide, quater-. nary ammonium salt and stabilizing agents to the emulsion before coating
  • the coatings were prepared as described in Example 1', except that the emulsion contained the addenda described in the following table..
  • the coatings were exposed on a Ib sensitometer and processed in the devel-. oper given for the times indicated. For convenience the speeds indicated in the table are measured as 100 (Ilog 11 E), where isthe exposure in meter candle seconds required to produce a density of 0.3 above fog.
  • Example 5 Additional of one or all of the polyethylene 35 oxide, the quaternary ammonium salt, and the azaindene, either to the emulsion or to the developer
  • The. coatings were prepared as described in Example 1, except that the emulsion contained the addenda described in the following table.
  • The. coatings were ex- 40 posed on a Ib sensitorneter and processed in the developer's" given, for the indicated times.
  • Example 7 Additi0n of both the polyethylene oxide and the quaternary ammonium salt to the emulsion before coating To an emulsion similar to that described in Example lythe following were added. The coatings were exposed and processed as in Example 1.
  • the data can. be quickly assessed by noting that the speed values (of samples 907, 908 and 909) 7700, 10,900, 8850, 12,200 and 15,000 represent development with the Gram quaternary compound present in neither emulsion nor Sample Compound iggi 30/ amma F g developer. Agx The example clearlyil'lustrates that the quaternary ammonium compounds are highly efiective when present 1.7 7, 550 1. 25 .20 in the developer alone or together with thepolyethylene 11,400 1.10 14 oxides, for the development of emulsions tree ofl, or 9 900 27 containing either or both of these sensitizing agents.
  • Example 8 Additional of different polyethylene oxides and quaternary ammonium salts to the emulsion before coating To an emulsion similar to that described in Example 1, the following were added. The coatings were exposed and processed as in Example 1.
  • the emulsions of Example 12 can, of course, contain the indicated quaternary ammonium compounds to further increase the light-sensitivity or additionally the other. sensitizing agents referred to above prior to the examples.
  • the chemical sensitizing agents and other addenda which we have described may be used. in various kinds of photographic emulsions. In addition to being useful in non-optically sensitized emulsions they may also be used in orthochromatic, panchromatic and X-ray emulsions. They may be added to the emulsion before or after any sensitizing dyes which are used.
  • Various silver salts may be used as the sensitive salt such as silver bromide, silver iodide, silver chlorideor mixed silver halides such as silver chlorobromide or'silver bromoiodide.
  • 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. 7
  • the dispersing agent for the silver halide may be gelatin or other colloidal material such as collodion, albumin, cellulose derivatives or synthetic resins.
  • an alkylene oxide polymer selected from the class consisting of (1) polyalkylene glycols and (2) condensation products of alkylene oxide with organic compounds containing an active hydrogen atom, said alkylene oxide containing from 2 to 4 carbon atoms and said alkylene oxide polymer having a molecular weight of at least 300, and a bis-quaternary ammonium salt silver halide chemical sensitizing agent the quaternary ammonium groups of
  • the emulsion of claim 1 containing as a fog inhibiting agent 4-hydroxy-6-alkyl-1,3,3a,7-tetraazaindene 3.
  • the emulsion, of claim 8 containing as a fog inhibiting agent 4-hydroxy-6-methyl-l,3,3a,7-tetraazaindene.
  • the method of increasing the sensitivity of a silver. halide emulsion which comprises exposing said emulsion and developing it in the presenceof an alkylene oxide polymer selected from the class consisting of (1) polyalkylene glycols and (2) condensation products of alkylene oxide with organic compounds containing an active hydrogen atom, said alkylene oxide. containing from 2 to 4 carbon atoms and said alkylene oxide polymer having a molecular weight of at. least 300, and a bis-quaternary ammoniumsalt silver halide sensitizing agent, the quaternary ammonium groups of which are linked together by achain of at least seven atoms. 1 r
  • polyalkylene oxide is polyethylene oxide oleyl etherand the quaternary ammonium salt isdecamethylenea-w-bis(oxymethyl pyridinium) perchlorate.

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  • Spectroscopy & Molecular Physics (AREA)
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US550495A 1955-12-01 1955-12-01 Photographic emulsions sensitized with alkylene oxide polymers and quaternary ammonium compounds Expired - Lifetime US2886437A (en)

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BE553031D BE553031A (en, 2012) 1955-12-01
US550495A US2886437A (en) 1955-12-01 1955-12-01 Photographic emulsions sensitized with alkylene oxide polymers and quaternary ammonium compounds
FR1170223D FR1170223A (fr) 1955-12-01 1956-11-26 Procédé pour accroître la sensibilité des émulsions photosensibles et nouveaux produits pour sa mise en oeuvre
DEE13286A DE1048146B (de) 1955-12-01 1956-11-28 Verfahren zur Steigerung der Empfindlichkeit von Halogensilberemulsionen
GB36640/56A GB871801A (en) 1955-12-01 1956-11-30 Improvements in photographic reproduction processes and in photographic silver halide emulsions therefor
US746131A US3017271A (en) 1955-12-01 1958-07-02 Photographic emulsions sensitized with alkylene oxide polymers and quaternary ammonium salts

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GB (1) GB871801A (en, 2012)

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3017270A (en) * 1958-03-31 1962-01-16 Eastman Kodak Co Photographic silver halide diffusion transfer process
US3062645A (en) * 1957-11-27 1962-11-06 Eastman Kodak Co Sensitization of photographic emulsions to be developed with p-phenylenediamine developing agents
US3113026A (en) * 1959-01-19 1963-12-03 Gen Aniline & Film Corp Polyvinyl alcohol photographic silver halide emulsions
DE1159267B (de) * 1960-05-12 1963-12-12 Gen Aniline & Film Corp Verfahren zur Erhoehung der Empfindlichkeit photographischer Materialien, lichtempfindliche Materialien, Halogensilberemulsionen und Entwickler hierfuer
US3128183A (en) * 1960-06-17 1964-04-07 Eastman Kodak Co Photographic halide emulsions sensitized with alkylene oxide polymers and aliphatic amines
US3146102A (en) * 1960-08-22 1964-08-25 Eastman Kodak Co Photographic multicolor diffusion transfer process using dye developers
US3158483A (en) * 1957-03-08 1964-11-24 Eastman Kodak Co Photographic developers containing polyalkylene glycols
US3173786A (en) * 1960-08-22 1965-03-16 Polaroid Corp Color diffusion transfer process, element and composition therefor
US3260597A (en) * 1960-12-02 1966-07-12 Eastman Kodak Co Photographic multicolor diffusion transfer process using dye developers and development arrestors
US3957491A (en) * 1972-09-04 1976-05-18 Fuji Photo Film Co., Ltd. Silver halide photographic material containing an organic compound having a covalent nitrogen-halogen bond as sensitizer
US4011083A (en) * 1974-12-10 1977-03-08 Eastman Kodak Company Surface sensitive silver halide emulsion containing a silver complexing azaindene to reduce desensitization of optical sensitizing dye incorporated therein
US4241164A (en) * 1976-12-30 1980-12-23 Fuji Photo Film Co., Ltd. Highly-sensitive high-contrast photographic materials
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0239363A2 (en) 1986-03-25 1987-09-30 Konica Corporation Light-sensitive silver halide photographic material feasible for high speed processing
US5492805A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Blocked leuco dyes for photothermographic elements
US5492804A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Chromogenic leuco redox-dye-releasing compounds for photothermographic elements
US5492803A (en) * 1995-01-06 1996-02-20 Minnesota Mining And Manufacturing Company Hydrazide redox-dye-releasing compounds for photothermographic elements
US5550013A (en) * 1994-12-22 1996-08-27 Eastman Kodak Company High chloride emulsions having high sensitivity and low fog and improved photographic responses of HIRF, higher gamma, and shoulder density
US5891615A (en) * 1997-04-08 1999-04-06 Imation Corp. Chemical sensitization of photothermographic silver halide emulsions
US5928857A (en) * 1994-11-16 1999-07-27 Minnesota Mining And Manufacturing Company Photothermographic element with improved adherence between layers
US5939249A (en) * 1997-06-24 1999-08-17 Imation Corp. Photothermographic element with iridium and copper doped silver halide grains
US6117624A (en) * 1993-06-04 2000-09-12 Eastman Kodak Company Infrared sensitized, photothermographic article
US20090081578A1 (en) * 2007-09-21 2009-03-26 Carestream Health, Inc. Method of preparing silver carboxylate soaps
US20090181332A1 (en) * 2008-01-14 2009-07-16 William Donald Ramsden Protective overcoats for thermally developable materials
WO2015148028A1 (en) 2014-03-24 2015-10-01 Carestream Health, Inc. Thermally developable imaging materials
WO2016073086A1 (en) 2014-11-04 2016-05-12 Carestream Health, Inc. Image forming materials, preparations, and compositions
WO2016195950A1 (en) 2015-06-02 2016-12-08 Carestream Health, Inc. Thermally developable imaging materials and methods
WO2017123444A1 (en) 2016-01-15 2017-07-20 Carestream Health, Inc. Method of preparing silver carboxylate soaps

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JPS5036979B1 (en, 2012) * 1971-03-04 1975-11-28
JPS576092B2 (en, 2012) * 1971-12-28 1982-02-03
JPS5232569B2 (en, 2012) * 1972-08-31 1977-08-23
JPS5284734A (en) * 1976-10-04 1977-07-14 Fuji Photo Film Co Ltd Photographic image formation
JPS564139A (en) * 1979-06-22 1981-01-17 Konishiroku Photo Ind Co Ltd High contrast silver image forming method

Citations (3)

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US2271623A (en) * 1939-03-30 1942-02-03 Eastman Kodak Co Photographic emulsion
US2410690A (en) * 1943-08-26 1946-11-05 Eastman Kodak Co Method of improving the sensitivity characteristics of emulsions
US2716062A (en) * 1953-07-01 1955-08-23 Eastman Kodak Co 4-hydroxy-6-alkyl-1, 3, 3a, 7-tetrazaindene stabilizers for emulsions sensitized with alkylene oxide polymers

Patent Citations (3)

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US2271623A (en) * 1939-03-30 1942-02-03 Eastman Kodak Co Photographic emulsion
US2410690A (en) * 1943-08-26 1946-11-05 Eastman Kodak Co Method of improving the sensitivity characteristics of emulsions
US2716062A (en) * 1953-07-01 1955-08-23 Eastman Kodak Co 4-hydroxy-6-alkyl-1, 3, 3a, 7-tetrazaindene stabilizers for emulsions sensitized with alkylene oxide polymers

Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3158483A (en) * 1957-03-08 1964-11-24 Eastman Kodak Co Photographic developers containing polyalkylene glycols
US3062645A (en) * 1957-11-27 1962-11-06 Eastman Kodak Co Sensitization of photographic emulsions to be developed with p-phenylenediamine developing agents
US3017270A (en) * 1958-03-31 1962-01-16 Eastman Kodak Co Photographic silver halide diffusion transfer process
US3113026A (en) * 1959-01-19 1963-12-03 Gen Aniline & Film Corp Polyvinyl alcohol photographic silver halide emulsions
DE1159267B (de) * 1960-05-12 1963-12-12 Gen Aniline & Film Corp Verfahren zur Erhoehung der Empfindlichkeit photographischer Materialien, lichtempfindliche Materialien, Halogensilberemulsionen und Entwickler hierfuer
US3128183A (en) * 1960-06-17 1964-04-07 Eastman Kodak Co Photographic halide emulsions sensitized with alkylene oxide polymers and aliphatic amines
US3146102A (en) * 1960-08-22 1964-08-25 Eastman Kodak Co Photographic multicolor diffusion transfer process using dye developers
US3173786A (en) * 1960-08-22 1965-03-16 Polaroid Corp Color diffusion transfer process, element and composition therefor
US3260597A (en) * 1960-12-02 1966-07-12 Eastman Kodak Co Photographic multicolor diffusion transfer process using dye developers and development arrestors
US3957491A (en) * 1972-09-04 1976-05-18 Fuji Photo Film Co., Ltd. Silver halide photographic material containing an organic compound having a covalent nitrogen-halogen bond as sensitizer
US4011083A (en) * 1974-12-10 1977-03-08 Eastman Kodak Company Surface sensitive silver halide emulsion containing a silver complexing azaindene to reduce desensitization of optical sensitizing dye incorporated therein
US4241164A (en) * 1976-12-30 1980-12-23 Fuji Photo Film Co., Ltd. Highly-sensitive high-contrast photographic materials
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0239363A2 (en) 1986-03-25 1987-09-30 Konica Corporation Light-sensitive silver halide photographic material feasible for high speed processing
US6117624A (en) * 1993-06-04 2000-09-12 Eastman Kodak Company Infrared sensitized, photothermographic article
US5696289A (en) * 1994-06-30 1997-12-09 Minnesota Mining And Manufacturing Company Blocked leuco dyes for photothermographic elements
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BE553031A (en, 2012)
GB871801A (en) 1961-06-28
FR1170223A (fr) 1959-01-12

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