US3874946A - Photothermographic element, composition and process - Google Patents

Photothermographic element, composition and process Download PDF

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Publication number
US3874946A
US3874946A US443892A US44389274A US3874946A US 3874946 A US3874946 A US 3874946A US 443892 A US443892 A US 443892A US 44389274 A US44389274 A US 44389274A US 3874946 A US3874946 A US 3874946A
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photothermographic
composition
mole
bromine compound
silver
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Lorenzo F Costa
Allan James A Van
Frank Grum
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to US443892A priority Critical patent/US3874946A/en
Priority to CA217,922A priority patent/CA1045876A/en
Priority to CH197975A priority patent/CH609160A5/xx
Priority to DE2506815A priority patent/DE2506815C3/de
Priority to FR7504915A priority patent/FR2261555B1/fr
Priority to BE153507A priority patent/BE825716A/xx
Priority to GB7007/75A priority patent/GB1495335A/en
Priority to JP2079175A priority patent/JPS54165B2/ja
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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
    • G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
    • G03C1/498—Photothermographic systems, e.g. dry silver
    • G03C1/49836—Additives
    • G03C1/49845—Active additives, e.g. toners, stabilisers, sensitisers

Definitions

  • ABSTRACT A stabilizer precursor comprising a compound which is a photolytically active polybrominated organic compound comprising (a) a 2,4-bis(tribromomethyl)-striazine, (b) a polybromoalkylsulfonyl compound having an aromatic chromophore group, or (c) a combination of the described stabilizer precursors, in a photothermographic element or compostion comprising photographic silver halide provides improved postprocessing stability of the element or composition.
  • the described stabilizer precursors are useful in photothermographic materials, for example, comprising photographic silver halide and an oxidationreduction image-forming combination comprising a heavy metal salt oxidizing agent with a reducing agent.
  • a developed visible image is provided after imagewise exposure by overall heating the photothermographic material to moderately elevated temperatures.
  • This invention relates to certain photolytically active polybrominated stabilizer precursors and photothermographic elements, compositions and processes using said precursors to provide improved stable images.
  • a photothermographic element comprising (a) photographic silver halide in association with (b) an oxidation-reduction imageforming combination comprising (i) a heavy metal salt oxidizing agent with (ii) an organic reducing agent, (c) a polymeric binder for the layer and (d) a photolytically active polybrominated organic compound stabilizer precursor as described.
  • a photothermographic composition comprising photographic silver halide, a polymeric binder and a photolytically active polybrominated organic compound stabilizer precursor as described.
  • a further aspect relates to such photographic compositions which are photothermographic materials.
  • a further aspect relates to a method of developing a stable image in a photothermographic element comprising the described photographic silver halide in association with the oxidation-reduction image-forming combination and the described stabilizer precursors.
  • the photothermographic element employed for providing such an image can contain a reducing agent, a light-sensitive silver salt of an organic acid, such as silver behenate, as an oxidizing agent and a low concentration of photographic silver halide.
  • a reducing agent such as a light-sensitive silver salt of an organic acid, such as silver behenate
  • Such photothermographic materials are described, for example, in U.S. Pat. No. 3,457,075 of Morgan, et al., issued July 22, 1969; U.S. Pat. No. 3,152,904 of Sorensen, et al., issued Oct. 13, 1964; British Specification No. 1,161,777 published Aug. 20, 1969; U.S. Pat. No. 3,392,020 of Yutzy, et al., issued July 9, 1968; U.S. Pat. No. 3,707,377 of Tiers, et al., issued Dec. 26, 1972 and in Research Disclosure, January, 1973, pages 16-21.
  • Another method proposed for solving the problem of post-processing instability is to provide a photothermographic combination in which the oxidationreduction image-forming combination is on one sheet of material and the latent image-forming photographic silver halide on a separate sheet. The sheets are separated after imagewise exposure such as described in U.S. Pat. No. 3,152,904.
  • a further means proposed for stabilization involves swabbing a 1% solution of phenylmercaptotetrazole onto the surface of the overall heated photothermographic material or rubbing benzotriazole into the surface of the photothermographic element. These proposed means for stabilization are not useful for large volume handling of heat developable photographic materials.
  • l-lalogenated organic compounds have been employed in photographic materials for various purposes, such as antifoggants.
  • l-lalogenated organic antifoggants for photographic emulsions are described, for example, in U.S. Pat. No. 3,128,187 of Segal, et al., issued Apr. 7, 1964; U.S. Pat. No. 3,232,762 of Ford, et al., issued Feb. 1, 1966; U.S. Pat. No. 2,732,303 ofMorgan, et al.,
  • Photographic materials which do not contain photographic silver halide and comprising tribromomethylsulfonyl derivatives of certain heterocyclic compounds such as benzothiazole compounds and benzimidazole compounds are described in Canadian Pat. No. 831,465 issued Jan. 6, 1970. This patent, however, does not described photothermographic materials containing photographic silver halide.
  • photothermographic materials comprising an image-forming combination containing photographic silver halide which have improvedpost-processing image stability, that is reduced background density and no significant decrease in desired maximum density when employing a halogen-containing stabilizer precursor.
  • R is alkyl containing 1 to 6 carbon atoms
  • R is hydrogen or a bromine atom
  • R is a bromine atom or a carbamoyl group
  • R is an aromatic chromophore group which has the property of imparting to said bromine compound stabilizer precursor the ability to absorb electromagnetic radiation having a wavelength between about 250 and 385 nm; and at least one of R R and R is or contains a bromine atom.
  • a photothermographic element comprising a support having thereon a layer comprising (a) photographic silver halide in association with (b) an oxidation-reduction image-forming combination comprising (i) a heavy metal salt oxidizing agent, preferably a silver salt oxidizing agent, with (ii) an organic reducing agent, (c) a polymeric binder for the layer and (d) a bromine compound stabilizer precursor as described.
  • a latent image in the described photothermographic element or composition can be developed by overall heating the element or composition to moderately elevated temperatures.
  • bromine compound stabilizer precursors as described within the above formulas, can be employed according to the invention to provide improved post-processing stability without significantly adversely affecting desired properties of the photothermographic material. 1
  • Different tests can be employed to determin whether compounds or materials are useful as stabilizer precursors as described depending upon the particular photothermographic element, composition, desired im- 7 age, processing conditions and the like.
  • One test which can be employed for certain photothermographic elements is as follows: I
  • a silver behenate-behenic acid dispersion (A) is prepared by ball-milling the following components for '72? hours:
  • a photothermographic element is prepared by combining 141 m1 of the described dispersion (A) with the following addenda, mixing thoroughly and coating at 0.63 g of composition per square decimeter on a suitable paper support:
  • organic solvent solution typically 1 1.0 ml
  • acetone containing polybromo stabilizer precursor according to the invention (typically organic solvent solution containing about 3% by weight of stabilizer precursor according to the invention) to'the moiety which upon combination with silver ions or atoms prevents instability due to roomlight expo-. sure.
  • polybromo stabilizer precursor according to the invention typically organic solvent solution containing about 3% by weight of stabilizer precursor according to the invention
  • the exact mechanism of stabilization is not fully understood. It is believed, however, that upon imagewise exposure of a photothermographic material containing photographic silver halide to actinic radiation, latent image specks of metallic silver are formed in the photographic silver halide remaining in the background areas of the photothermographic element to produce unwanted background printup, especially after subsequent overall heating.
  • the bromine from the described stabilizer precursors of the invention is at least in part released photolytically and attacks and destroys the latent image metallic silver sites before they produce printup, that is before background fog is produced, without attacking the developed silver image to any significant degree. It is believed that the photolytically released bromine comprises free radicals which reoxidize the latent image silver atoms in the photographic silver halide to silver ions.
  • bromine containing stabilizer precursors according to the invention have sufficient thermal stability for use in the described photothermographic materials. This is illustrated in the following comparative examples.
  • One useful class of stabilizer precursors according to the invention within the described formulas comprises a compound wherein described R and R are each bromine atoms and R is phenyl, naphthyl or benzothiazole.
  • aromatic chromophore group as employed herein is intended to mean a group which imparts to the bromine compound stabilizer precursor containing the group the ability to release at least one bromine atom when exposed to electromagnetic radiation having a wavelength between about 250 and 385 nm.
  • aromatic chromophore groups can provide this desired property.
  • Especially useful aromatic chromophore groups include phenyl, naphthyl or benzothiazole. These groups can contain substituent groups which do not adversely affect the stabilizing action of the stabilizer precursors according to the invention, such as methyl, ethyl and the like.
  • polybromo or polybrominated compound as employed herein is intended to mean a compound as described containing two or more bromine atoms.
  • Useful stabilizer precursors as described include, for example, the following compounds:
  • 2-tribromomethylsulfonylbenzothiazole 2,4-bis(tribromomethyl)-6-methyltriazine 2,2-dibromo-2-phenylsulfonylacetamide
  • the described polybrominated organic compounds can be prepared by methods known in the art.
  • the parent organic compound can be brominated employing conventional bromination processes.
  • An example preparation is the preparation of 2- tribromomethylsulfonylbenzothiazole which comprises adding dropwise at 5 to 10C. 150 milliliters of bromine to a stirred solution of 240 grams of sodium hydroxide in 2.5 liters of water.
  • Another example of a useful preparation is the preparation of 2,4bis(tribromomethyl)-6-methyltriazine in which a mixture of 140 grams of 2,4,6trimethyltriazine and 520 grams of sodium acetate dispersed in 2,300 milliliters of acetic acid is heated to 70C. while adding 520 milliliters of bromine slowly with stirring over a 2- hour period. The temperature is raised to 90C. for one hour and the mixture is allowed to stand about 16 hours. After standing, 2 liters of water is added and the solid mixture resulting is collected by filtration and recrystallized from acetonitrile.
  • Some halogenated organic compound impurities can be present in the resulting compositions. These impurities can be separated, if desired, before mixing the desired brominated compound stabilizer precursor with the described photothermographic materials.
  • the described polybrominated stabilizer precursors according to the invention are useful in a variety of silver halide photothermorgaphic materials.
  • the useful concentration of stabilizer precursor according to the invention will depend upon different factors such as the particular photothermographic ele- .ment, particular components of the photothermographic material, desired image, desired image stability and the like.
  • a useful concentration of stabilizer precursor according to the invention is about 0.002 mole to about 0.75 mole of the described stabilizer precursor per mole of total silver in the photothermographic material.
  • An especially useful concentration is about 0.01 mole to about 0.5 mole of the described stabilizer precursor per mole of total silver in the photothermographic material.
  • the total concentration of stabilizer precursors is within the described concentration range. The optimum concentration useful can be determined based on the described factors.
  • Typical photothermographic materials in which the stabilizer precursors of the invention are useful are described, for example, in U.S. Pat. No. 3,457,075 of Morgan, et al., issued July 22, 1969; U.S. Pat. No. 3,152,904 of Sorensen, et al., issued Oct. 13, 1964; U.S. Pat. No. 3,429,706 of Shepard, et al., issued Feb. 25, 1969; U.S. Pat. No. 3,672,904 of deMauriac, issued June 27, 1972 and Research Disclosure, January, 1973, pages 16-21.
  • the stabilizer precursors of the invention are especially useful in photothermographic materials comprising (a) photographic silver halide in association with (b) an oxidation-reduction image-forming combination comprising (i) a silver salt of a long-chain fatty acid, such as silver behenate, with (ii) a phenolic reducing agent, (6) a poly(vinyl butyral) binder for the layer, (d) a toner, also known as an activator-toning agent or known as a toner-accelerator, comprising 1- (2H)-phthalazinone, succinimide or N-hydroxy-1,8- naphthalimide, and (e) a spectral sensitizing dye.
  • An especially useful embodiment of the invention is a photothermographic element comprising a support having thereon a layer comprising (a) photographic silver halide in association with (b) an oxidationreduction image-forming combination comprising (i) silver behenate, with (ii) a sulfonamidophenol reducing agent, (c) a poly(vinyl butyral) binder for the layer, (d) a toner comprising l-(2H)-phthalazinone, succinimide or N-hydroxy-l,8-naphthalimide, and (e) a stabilizing concentration of 2-tribromomethylsulfonylbenzothiazole, 2,4-bis(tribromomethyl)-6-methyltriazine or 2,2-dibromo-2 -phenylsulfonylacetamide.
  • the described photothermographic materials according to the invention comprise a photosensitive component which is photographic silver halide.
  • a photosensitive component which is photographic silver halide.
  • the latent image silver resulting from the photosensitive salt acts as a catalyst for the described oxidationreduction image-forming combination.
  • a typical concentration range of photographic silver halide is from about 0.01
  • photographic silver halide mole to about 20.0 moles of photographic silver halide per mole of silver salt oxidizing agent, for example, per mole or silver behenate.
  • Other photosensitive silver salts can be used in combination with the photographic silver halide if desired.
  • Useful photosensitive silver salts include silver-dye complexes.
  • Preferred photographic silver halides are silver chloride, silver bromide, silver bromoiodide, silver chlorobromoiodide or mixtures thereof. Very fine-grain photographic silver halide is especially useful although coarse or fine-grain photosensitive silver halide can be employed if desired.
  • the photographic silver halide can be prepared by any of the procedures known in the photographic art.
  • the photothermographic elements and compositions according to the invention comprise an oxidationreduction image-forming combination which contains a heavy metal salt oxidizing agent, preferably a silver salt oxidizing agent, especially a silver salt of a longchain fatty acid.
  • a heavy metal salt oxidizing agent preferably a silver salt oxidizing agent, especially a silver salt of a longchain fatty acid.
  • Such silver salt oxidizing agents are resistant to darkening upon illumination.
  • useful silver salts of long-chain fatty acids are those containing about 17 to 30 carbon atoms.
  • Compounds which are useful silver salt oxidizing agents include: silver behenate, silver stearate, silver oleate, silver laurate, silver hydroxystearate, silver caprate, silver myristate and silver palmitate.
  • Silver salts which are not silver salts of long-chain fatty acids can be employed in combination with the silver salts of long-chain fatty acids.
  • Such silver salt oxidizing agents which are useful include, for example, silver benzoate, silver benzotriazole, silver terephthalate, silver phthalate and the like.
  • Examples of other heavy metal salt oxidizing agents are gold stearate, mercury behenate and gold behenate. Combinations of oxidizing agents are also useful.
  • the described photothermographic elements and compositions can comprise various organic reducing agents.
  • Useful reducing agents which can be employed with the described stabilizer precursors include substituted phenols and naphthols, for example, bis-beta naphthols.
  • Suitable bis-beta-naphthols include, for example, 2,2'-dihydroxy-l,l -binaphthyl, 6,6'-dibromo- 2,2'-dihydroxy-l,l -binaphthyl or 6,6-dinitro-2,2 dihydroxy-l ,l '-binaphthyl.
  • reducing agents which can be employed in photothermographic elements, according to the invention, include polyhydroxybenzenes such as hydroquinone, alkyl-substituted hydroquinones such as tertiary butylhydroquinone, methylhydroquinone, 2,5-dimethylhydroquinone and 2,6-dimethylhydroquinone; catechols and pyrogallols, chloro-substituted hydroquinones such as chlorohydroquinone or dichlorohydroquinone; alkoxy-substituted hydroquinone such as methoxyhydroquinone or ethoxyhydroquinone; aminophenol reducing agents, such as 2,4-diaminophenols and methylaminophenols; ascorbic acid reducing agents such as ascorbic acid, ascorbic acid ketals and ascorbic acid derivatives; hydroxylamine reducing agents; 3-pyrazolidone reducing agents such as l-phenyl-3-pyrazolidone
  • Especially useful reducing agents which can be employed in the photothermographic materials according to the invention are sulfonamidophenol reducing agents as described in Research Disclosure, January,
  • R is phenyl, naphthyl, methylphenyl, thi-. enyl, quinolinyl, thiazyl, or alkyl containing 1 to 4 car- I bon atoms, such as methyl, ethyl, propyl or butyl'
  • R is hydrogen, R SO Nl-l, alkoxy containing 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy and butoxy, bromine or chlorine
  • R is hydrogen, bromine, chlorine, alkyl containing 1 to 4 carbon atoms, as described, or alkoxy containing 1 to 4 carbon atoms, such as methoxy, ethoxy and propoxy.
  • R, R and/or R can contain substituent groups which do not adversely affect the reducing properties of the described sulfonamidophenol reducing agents or the desired sensitometric properties of the photothermographic elements and materials of the invention.
  • substituent groups which can be present are alkyl containing 1 to scribed, for example, in Belgian Pat. No. 766,590 is- 1 sued June 15, 1971 and in Research Disclosure, January, 1973, pages 16-21. Combinations of toning agents can be employed in the photothermographic materials according to the invention if desired.
  • Typical toning agents include, for example, phthalimide, N- hydroxyphthalimide, N-potassium phthalimide, succinimide, N-hydroxy-l ,S-naphthalimide and N- hydroxysuccinimide. In some cases other toningagents. i
  • Typical stabilizer precursors which can be employed in combination with the stabilizer precursors of the invention include, for example, azole thioethers and blocked azoline thione stabilizer precursors as described in Belgian Pat. No. 768,071 issued July 30,
  • a photothermographic element or composition as described according to the invention can contain various colloids and polymers alone or in combination as vehicles, binding agents and in various layers.
  • Suitable materials can be hydrophobic or-hydrophilic. They are transparent or translucent and include both naturallyoccurring substances such as proteins, for example, gelatin, gelatin derivatives, cellulose derivatives, polysaccharides such as dextran, gumarabic and the like; and synthetic polymeric substances such as water soluble polyvinyl compounds like poly(vinyl pyrrolidone), acrylamide polymers and the like.
  • Other synthetic polymeric compounds which can be employed include dispersed vinyl compounds such as in latex form and particularly those which increase dimensional stability of photographic materials.
  • Effective polymers include waterinsoluble polymers of alkyl, acrylates and methacrylates, acrylic acid, sulfoalkyl acrylates,methacrylates and those which have crosslinlcing sites which facilitate hardening or curing as well as those having recurring sulfobetaine units as described in Canadian Pat. No. 774,054.
  • Especially useful high molecular weight materials and resins include poly(vinyl butyral), cellulose acetate butyrate, poly(methyl methacrylate), poly(vinyl pyrrolidone), ethylcellulose, polystyrene, poly(vinyl chloride), chlorinated rubber, polyisobutylene, butadiene-styrene copolymers, vinyl chloride-vinyl acetate copolymers, copolymers of vinyl acetate, vinyl chloride andmaleic acid and poly(vinyl alcohol).
  • the useful concentration of reducing agent accord ing to the invention will vary depending upon the particular photothermographic element, desired image, processing conditions, particular stabilizer precursor employed and the like.
  • a useful concentration of reducing agent is typically from about 0.2 mole to about 2.0 moles of reducing agent per mole of photographic silver halide.
  • a useful concentration of reducing agent in relationship to oxidizing agent, such as silver behenate or silver stearate, is typically from about 0.01 mole to about moles of reducing agent per mole of silver salt of a long-chain fatty acid, such as per mole of silver behenate, in the photothermographic material.
  • Reducing agents can be employed in combination. When combinations are employed, the total concentration of reducing agent is typically within the described concentration range.
  • Photothermographic materials according to the invention can contain development modifiers that function as speed-increasing compounds, hardeners, antistatic layers, plasticizers and lubricants, coating aids, brighteners, spectral sensitizing dyes, absorbing and fil ter dyes, also as described in the Product Licensing Index, Volume 92, December, 1971, publication 9232, pages 1071 10.
  • the photothermographic elements according to the invention can comprise a wide variety of supports.
  • Typical supports include cellulose nitrate film, cellulose ester film, poly(vinyl acetal) film, polystyrene film, poly(ethylene terephthalate) film, polycarbonate film, film supports as described in U.S. Pat. No. 3,634,089 of Hamb, issued Jan. 11, 1972 and U.S. Pat. No. 3,725,070 of Hamb, eta1., issued Apr. 3, 1973 and related films or resinous materials, as well as glass, paper, metal and the like supports which can withstand the processing temperatures employed according to the invention.
  • a flexible support is employed.
  • the photothermographic compositions and other compositions according to the invention can be coated on a suitable support by various coating procedures including dip coating, air knife coating, curtain coating or. extrusion coating using hoppers such as described in U.S. Pat. No. 3,681,294 of Beguin issued June 15, 1954. If desired, two or more layers can be coated simultaneously such as described in U.S. Pat. No. 2,761,791 of Russell, issued Sept. 4, 1956 and British Pat. No. 837,095. r
  • Spectral sensitizing dyes can be used in the described photothermographic elements and compositions of the invention to confer additional sensitivity to the ele- -ments and compositions of the invention.
  • Useful sensitizing dyes are described, for example, in the Product Licensing Index, Volume 92, December, 1971, publication 9232, pages 107-110, paragraph XV.
  • the resulting latent image can be developed merely by overall heating the element to moderately elevated temperatures.
  • This overall heating merely involves heating the described element overall to a temperature within the range of from about C. to about 250C. such as for about 0.5 to about 60 seconds.
  • a higher or lower temperature within the described range can be employed depending upon the desired image, particular reducing agent, and the like.
  • a lower processing temperature is desired.
  • a preferred processing temperature range is from about C. to about C.
  • a developed and stabilized image is typically produced within several seconds, such as from about 0.5 seconds to about 60 seconds.
  • the heating means can be a simple hot plate, iron, roller or the like.
  • Processing is usually carried out under ambient conditions of pressure and humidity. Conditions outside normal atmospheric pressure and humidity can be employed if desired.
  • the described stabilizer precursor according to the invention can be in any suitable location in the photothermographic material according to the invention which provides the desired stabilized image.
  • one or more of the components of the photothermographic element according to the invention can be in one or more layers of the element.
  • the described stabilizer precursors according to the invention can be used in, for example, photothermographic materials comprising photographic silver halide as described in U.S. Pat. No. 3,679,426 of Youngquist, issued July 25, 1972; U.S. Pat. No. 3,667,958 of Evans, issued June 6, 1972; U.S. Pat. No. 3,667,959 of Bojara and deMauriac, issued June 6, 1972; Belgian Pat. No. 766,590 issued June 15, 1971; U.S. Pat. No. 3,672,904 of deMauriac, issued June 27, 1972; Belgian Pat. No. 772,371 issued Oct. 15, 1971 and U.S. application Ser. No. 272,832 of Evans and McLaen, filed July 18, 1972.
  • EXAMPLE 1 This is a comparative example.
  • EXAMPLE 2 The procedure described in Example 1 is repeated with the exception that the described composition contained ll milliliters of an acetone solution containing 3% by weight of 2-tribromomethy1sulfonylbenzo-- thiazole; and, the acetone-toluene solvent mixture was reduced to 33 milliliters.
  • a silver behenate-behenic acid dispersion A is pre- 15 pared by ball-milling the following components for 72 hours:
  • the resulting photothermographic element was im.-. agewise exposed and then overall heated as described in Example 1. It was then exposed to 1,500 ft. candlessilver behenate 168.0 g behinrc afijdt fig-g g of light for 72 hours also as descr1bed in Example 1. p0 y vmy u yra g lithium Stem: 164 g
  • the resultlng sensitometric data are given in following acetone-toluene (1:1 parts by volume) 2.0 I Table I.
  • a photothermographic element is prepared by combining 141 ml. of the above-described dispersion (A) with the following addenda, mixing thoroughly and coating at 0.63 g of composition/dm on a suitable paper support:
  • composition is coated over the element at a coverage of 0.43 g/dm' thereby providing a protective layer containing approximately 10.76 mg cellulose acetate/dm of support.
  • the resulting photothermographic element is imagewise exposed for 1 second to tungsten light and then overall heated by contacting the photothermographic element for 2 seconds on a metal block heated to 150C.
  • the sensitometric results for the resulting developed image are given in following Table I.
  • the processed element is then subjected to 1,500 ft. candles of J1 EXAMPLE 3
  • a silver behenate dispersion is prepared by ballmilling the following components for hours:
  • amidophenol acetone solution containing 5% by weight 2,4-dihydroxybenzophenone -Continued tended to mean a compound according to the invention I j I 300 I which increases stability in the photothermographic z gtgg m material prior to imagewise exposure.
  • silicone i surfactant Silicone AFJO
  • Table ll indicates that the T80 treated which isatrade name of coatings do not provide useful images with the deii s i Electric scribed element, processing time and temperature listed.
  • Photolytic efficiency of stabi- I lizer precursors according to the invention can also be The fesultmg photothefmogfaphlc element tested employing the procedure in the following examovercoated with the following composition at 0.25 mili liliters per square decimeter:
  • the proposed stabilizer precursors can also be qualiin the same manner by dipping film strips into the soltively evaluated for relative photolytic efficiency by vents alone or into a solution of 2-tribromomethylsulpreparing solutions in the manner described for the fonylbenzothiazole, also referred to herein as TSB, rethermal stability test in Example 4. The solution is exspectively.
  • TSB 2-tribromomethylsulpreparing solutions in the manner described for the fonylbenzothiazole
  • the denbrated monochromator when protected with a filter sity of the color produced in the solution is observed combination that permits only radiation of wavelengths and an arbitrary reading of the density qualitatively is longer than 590 nanometers to pass.
  • the respective given to each solution of excellent, good, fair or poor. samples are then overall heated as indicated in the fol-
  • the relative photolytic efficiency ratings are given in lowing Table II employing the listed time and temperah f n i T bl [IL ture conditions.
  • the term con is used to The following compounds are tested: identify untreated film samples used as controls and the term S-C is used to identify solvent treated control Compound A 2-tribromomethylsulfonylbenzothiazole samples.
  • the TBQ and BMT treated samples are prepared in the same mannere as the solvent treated sample except, in place of the solvent, a solution is used comprising grams per liter of the stabilizer precursor in the solvent.
  • the TSB treated sample is prepared as described above except that the concentration of the solution was only 9 grams of TSB per liter.
  • the samples are dried overnight in the dark and treated in a fadeometer the next day.
  • the fadeometer is a standard testing apparatus which provides exposure to intense light.
  • the total reflected densities were measured from each sample at 550 nanometers after 4 hours and after 28 hours fading in the high intensity xenon arc fadeometer.
  • the measured densities are recorded in the following Table IV.
  • 3M Company Dry Silver Paper Type 7743 comprises 7 a paper support having thereon a photothermographic layer comprising a toner which is 1-(2H)- phthalazinone with 2,2'-methylenebis(4-methyl-6- tertiarybutylphenol), silver behenate, silver bromide, aluminum oxide, and tetrabromobutane.
  • the photothermographic layer is overcoated with a vinylacetate and vinylacetate-vinyl chloride copolymer layer. Tetrabromobutane is employed as a stabilizer.
  • a photothermographic element comprising a prising (i) a heavy metal salt oxidizing agent with (ii) an organic reducing agent, (c) a polymeric binder for the layer and (d) a bromine compound stabilizer precursor, the improvement wherein said bromine compound stabilizer precursor comprises a compound rep resented by the structure:
  • R is alkyl containing 1 to 6 carbon atoms, R is hydrogen or a bromine atom, R is a bromine atom or a carbamoyl group, R is an aromatic chromophore group which has the property of imparting to said bromine compound wherein said bromine compound stabilizer presursor is 2,4-bis(tribromomethyl)-6-methyltriazine.
  • a photothermographic element as in claim 1 wherein said bromine compound stabilizer precursor is 2,Z-dibromo-2-phenylsulfonylacetamide.
  • a photothermographic element as in claim 1 comprising about 0.002 mole to about 0.75 mole of said bromine compound stabilizer precursor per" mole of total silver ,said ,photothermographic element.
  • a photothermographic element comprising a support havingthereon a layer comprising a. photographic silver halide in association with b. an oxidation-reduction image-forming combination comprising i. silver behenate, with ii. a phenolic reducing agent,
  • a toner comprising phthalazinone, succinimide or N-hydroxy-l ,8-naphthalimide
  • a photothermographic composition comprising photographic silver halide, a polymeric binder and a bromine compound represented by the formula:
  • Rl is alkyl containing 1 to 6 carbon atoms, R s hydrogen or a bromine atom, R is a bromine atom or a carbamoyl group,
  • R is an aromatic chromophore group which has the property of imparting to said bromine compound stabilizer precursor the ability to absorb electromagnetic radiation having a wavelength between about 250 and 385 nm; and at least one of R, R and R is or contains a bromine atom.
  • photothermographic composition as in claim 8 wherein said bromine compound is 2- trlbromomethylsulfonylbenzothiazole.
  • photothermographic composition as in claim 8 comprising about 0.002 mole to about 0.75 mole of said bromine compound per mole of total silver in said composition.
  • a photothermographic composition comprising (a) photographic silver halide in association with (b) an ox dation-reduction image-forming combination comprising (i) a heavy metal salt oxidizing agent with (u) a reduclng agent, (c) a polymeric binder and (d) a bromine compound stabilizer precursor, the improvement wherein said bromine compound stabilizer prefursor comprises a compound represented by the strucure:
  • R is alkyl containing 1 to 6 carbon atoms, R s hydrogen or a bromine atom, R [S a bromine atom or a carbamoyl group,
  • R is an aromatic chromophore group, which has the property of imparting to said bromine compound stabilizer precursor the ability to absorb electromagnetic radiation having a wavelength between about 250 and 385 nm; and at least one or R, R
  • R is or contains a bromine atom.
  • a photothermographic composition as in claim 11 wherein said bromine compound stabilizer precursor is 2-tribromomethylsulfonylbenzothiazole.
  • a photothermographic composition as in claim 11 wherein said bromine compound stabilizer precursor is 2,2-dibromo-2-phenylsulfonylacetamide.
  • a phototheimographic composition as in claim 11 comprising about 0.002 mole to about 0.75 mole of said bromine compound stabilizer precursor per mole of total silver in said composition.
  • a photothermographic composition comprising a. photographic silver halide in association with b. an oxidation-reduction image-forming combination comprising i. silver behenate, with ii. a phenolic reducing agent, 0. a poly(vinyl butyral) binder for the composition, (1. a toner comprising phthalazinone, succinimide or N-hydroxy-1,8-naphthalimide, e. a spectral sensitizing dye, and f. about 0.015 to about 0.50 mole of 2- tribromomethylsulfonylbenzothiazole per mole of total silver in said composition.
  • a method of developing an image in a photothermographic element comprising a support having thereon a layer comprising (a) photographic silver halide in association with (b) an oxidation-reduction image-forming combination comprising (i) a silver salt oxidizing agent with (ii) a reducing agent, (c) a polymeric binder and (d) a bromine compound stabilizer precursor comprising a compound represented by the structure:
  • R is alkyl containing 1 to 6 carbon atoms
  • R is hydrogen or a bromine atom
  • R is a bromine atom or a carbamoyl group
  • R is an aromatic chromophore group which has the property of imparting to said bromine compound stabilizer precursor the ability to absorb electromagnetic radiation having a wavelength between about 250 and 385 nm; and at least one of R, R and R is or contains a bromine atom,
  • a method as in claim 18 of developing an image in a photothermographic element comprising a support having thereon a layer comprising a. photographic silver halide in association with 19 20 b. an oxidation-reduction image-forming combinae. a spectral sensitizing dye, and I tion comprising f. about 0.015 to about 0.50 mole of 2- i. silver behenate, with' tribromomethylsulfonylbenzothiazole per mole of ii. a phenolic reducing agent, total silver in said photothermographic element, c. a poly(vinyl butyral) binder, 5 comprising overall heating said element to about 80C.
  • a toner comprising phthalazinone, succinimide, or to about 170C. for about 0.5 to about 30 seconds.

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
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DE2506815A DE2506815C3 (de) 1974-02-19 1975-02-18 Photothermographisches Aufzeichnungsmaterial
FR7504915A FR2261555B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1974-02-19 1975-02-18
CH197975A CH609160A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1974-02-19 1975-02-18
BE153507A BE825716A (fr) 1974-02-19 1975-02-19 Nouveau produit photosensible thermodeveloppable
GB7007/75A GB1495335A (en) 1974-02-19 1975-02-19 Sensitive photothermographic material
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DE2745048A1 (de) * 1976-10-07 1978-04-13 Minnesota Mining & Mfg Photothermographische aufzeichnungsschicht
US4144062A (en) * 1976-07-08 1979-03-13 Eastman Kodak Company Organotellurium (II) and (IV) compounds in heat-developable photographic materials and process
FR2406227A1 (fr) * 1977-10-17 1979-05-11 Asahi Chemical Ind Perfectionnements a des materiaux formant l'image a sec
US4207108A (en) * 1976-11-04 1980-06-10 Eastman Kodak Company Silver halide photothermographic element, composition and process
US4212937A (en) * 1977-12-23 1980-07-15 Asahi Kasei Kogyo Kabushiki Kaisha Heat developable photosensitive materials
US4258129A (en) * 1974-10-31 1981-03-24 Fuji Photo Film Co., Ltd. Thermally developable light sensitive material using trivalent and tetravalent cerium compounds
US4292399A (en) * 1979-10-22 1981-09-29 Eastman Kodak Company Cobalt (III) complex imaging compositions having improved photographic properties
US4318977A (en) * 1979-10-22 1982-03-09 Eastman Kodak Company Cobalt (III) complex imaging compositions having improved photographic properties
US4452885A (en) * 1981-10-06 1984-06-05 Fuji Photo Film Co., Ltd. Heat-developable photographic material
US4459350A (en) * 1982-09-29 1984-07-10 Eastman Kodak Company Photothermographic material and processing comprising a substituted triazine
US4546075A (en) * 1982-09-09 1985-10-08 Fuji Photo Film Co., Ltd. Heat-developable photographic material
US4756999A (en) * 1985-11-20 1988-07-12 Minnesota Mining And Manufacturing Company Photothermographic materials
EP0605981A1 (en) * 1993-01-06 1994-07-13 Minnesota Mining And Manufacturing Company Photothermographic materials
US5340712A (en) * 1993-04-21 1994-08-23 Minnesota Mining And Manufacturing Company Antifoggants for photothermographic articles
EP0622666A1 (en) * 1993-04-29 1994-11-02 Minnesota Mining And Manufacturing Company Post-processing stabilizers for photothermographic articles
US5374514A (en) * 1993-01-06 1994-12-20 Kirk; Mark P. Photothermographic materials
EP0631176A1 (en) * 1993-06-08 1994-12-28 Minnesota Mining And Manufacturing Company Photothermographic materials
US5432287A (en) * 1993-12-17 1995-07-11 Minnesota Mining And Manufacturing Company Photothermographic materials
EP0802178A2 (en) 1996-02-23 1997-10-22 Fuji Photo Film Co., Ltd. Schiff base quinone complexes and optical recording materials comprising the same
US5952167A (en) * 1996-03-05 1999-09-14 Fuji Photo Film Co., Ltd. Photothermographic materials
US5958668A (en) * 1996-05-22 1999-09-28 Fuji Photo Film Co., Ltd. Recording material
EP0990946A1 (en) * 1998-09-30 2000-04-05 Fuji Photo Film Co., Ltd. Heat-developable photosensitive material
US6074813A (en) * 1996-03-28 2000-06-13 Fuji Photo Film, Co., Ltd. Polyhalomethane compound and photosensitive material
EP1041433A1 (en) * 1999-03-30 2000-10-04 Fuji Photo Film Co., Ltd. Heat-developable photosensitive material and method for forming image using the same
US6316670B1 (en) 1999-07-19 2001-11-13 Fuji Photo Film Co., Ltd. Polyhalogenomethylsulfonyl compound
US6350569B1 (en) 1999-03-30 2002-02-26 Fuji Photo Film Co., Ltd. Heat-developable photographic material
US6368778B1 (en) 2000-08-15 2002-04-09 Eastman Kodak Company Photothermographic materials providing improved image stability and methods of use
US6506548B1 (en) * 2001-12-11 2003-01-14 Eastman Kodak Company Silver halide photographic materials containing solubilized antifoggants
US6514678B1 (en) 2001-12-11 2003-02-04 Eastman Kodak Company Photothermographic materials containing solubilized antifoggants
US6518007B1 (en) * 2001-12-11 2003-02-11 Eastman Kodak Company Silver halide elements containing solubilized antifoggants and low fogging tabular silver halide grains
US20040074847A1 (en) * 2002-10-16 2004-04-22 Jaquess Percy A. Stable N-bromo-2-pyrrolidone and methods to make the same
EP1582919A1 (en) 2004-03-23 2005-10-05 Fuji Photo Film Co. Ltd. Silver halide photosensitive material and photothermographic material
US20060003272A1 (en) * 2004-06-09 2006-01-05 Konica Minolta Medical & Graphic, Inc. Photothermographic material, development method and thermal development device thereof
US20060014111A1 (en) * 2004-07-15 2006-01-19 Konica Minolta Medical & Graphic, Inc. Method of forming an image
EP1635216A1 (en) 2004-09-14 2006-03-15 Fuji Photo Film Co., Ltd. Photothermographic material
WO2007010777A1 (ja) 2005-07-20 2007-01-25 Konica Minolta Medical & Graphic, Inc. 画像形成方法
EP1953592A1 (en) 2007-02-02 2008-08-06 Konica Minolta Medical & Graphic, Inc. Photothermographic material
US7468241B1 (en) 2007-09-21 2008-12-23 Carestream Health, Inc. Processing latitude stabilizers for photothermographic materials
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
WO2017123444A1 (en) 2016-01-15 2017-07-20 Carestream Health, Inc. Method of preparing silver carboxylate soaps

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GB9121795D0 (en) * 1991-10-14 1991-11-27 Minnesota Mining & Mfg Positive-acting photothermographic materials

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US4258129A (en) * 1974-10-31 1981-03-24 Fuji Photo Film Co., Ltd. Thermally developable light sensitive material using trivalent and tetravalent cerium compounds
US4144062A (en) * 1976-07-08 1979-03-13 Eastman Kodak Company Organotellurium (II) and (IV) compounds in heat-developable photographic materials and process
US4152155A (en) * 1976-07-08 1979-05-01 Eastman Kodak Company Organotellurium (II) and (IV) compounds in heat-developable imaging materials and process with physically developable nuclei
DE2745048A1 (de) * 1976-10-07 1978-04-13 Minnesota Mining & Mfg Photothermographische aufzeichnungsschicht
US4207108A (en) * 1976-11-04 1980-06-10 Eastman Kodak Company Silver halide photothermographic element, composition and process
FR2406227A1 (fr) * 1977-10-17 1979-05-11 Asahi Chemical Ind Perfectionnements a des materiaux formant l'image a sec
US4234679A (en) * 1977-10-17 1980-11-18 Asahi Kasei Kogyo Kabushiki Kaisha Dry image forming materials
US4212937A (en) * 1977-12-23 1980-07-15 Asahi Kasei Kogyo Kabushiki Kaisha Heat developable photosensitive materials
US4292399A (en) * 1979-10-22 1981-09-29 Eastman Kodak Company Cobalt (III) complex imaging compositions having improved photographic properties
US4318977A (en) * 1979-10-22 1982-03-09 Eastman Kodak Company Cobalt (III) complex imaging compositions having improved photographic properties
US4452885A (en) * 1981-10-06 1984-06-05 Fuji Photo Film Co., Ltd. Heat-developable photographic material
US4546075A (en) * 1982-09-09 1985-10-08 Fuji Photo Film Co., Ltd. Heat-developable photographic material
US4459350A (en) * 1982-09-29 1984-07-10 Eastman Kodak Company Photothermographic material and processing comprising a substituted triazine
EP0107093A3 (en) * 1982-09-29 1985-05-15 Eastman Kodak Company Photothermographic recording material comprising a substituted triazine stabilizer precursor compound
US4756999A (en) * 1985-11-20 1988-07-12 Minnesota Mining And Manufacturing Company Photothermographic materials
EP0223606B1 (en) * 1985-11-20 1993-12-15 Minnesota Mining And Manufacturing Company Photothermographic materials
US5374514A (en) * 1993-01-06 1994-12-20 Kirk; Mark P. Photothermographic materials
EP0605981A1 (en) * 1993-01-06 1994-07-13 Minnesota Mining And Manufacturing Company Photothermographic materials
US5340712A (en) * 1993-04-21 1994-08-23 Minnesota Mining And Manufacturing Company Antifoggants for photothermographic articles
US5464737A (en) * 1993-04-29 1995-11-07 Minnesota Mining And Manufacturing Company Post-processing stabilizers for photothermographic articles
US5369000A (en) * 1993-04-29 1994-11-29 Minnesota Mining And Manufacturing Company Post-processing stabilizers for photothermographic articles
EP0622666A1 (en) * 1993-04-29 1994-11-02 Minnesota Mining And Manufacturing Company Post-processing stabilizers for photothermographic articles
EP0631176A1 (en) * 1993-06-08 1994-12-28 Minnesota Mining And Manufacturing Company Photothermographic materials
US5460938A (en) * 1993-06-08 1995-10-24 Minnesota Mining And Manufacturing Company Photothermographic materials
US5594143A (en) * 1993-06-08 1997-01-14 Imation Corp. Photothermographic materials
US5432287A (en) * 1993-12-17 1995-07-11 Minnesota Mining And Manufacturing Company Photothermographic materials
EP0802178A2 (en) 1996-02-23 1997-10-22 Fuji Photo Film Co., Ltd. Schiff base quinone complexes and optical recording materials comprising the same
US5952167A (en) * 1996-03-05 1999-09-14 Fuji Photo Film Co., Ltd. Photothermographic materials
US6074813A (en) * 1996-03-28 2000-06-13 Fuji Photo Film, Co., Ltd. Polyhalomethane compound and photosensitive material
US5958668A (en) * 1996-05-22 1999-09-28 Fuji Photo Film Co., Ltd. Recording material
EP0990946A1 (en) * 1998-09-30 2000-04-05 Fuji Photo Film Co., Ltd. Heat-developable photosensitive material
US6329134B1 (en) 1998-09-30 2001-12-11 Fuji Photo Film Co., Ltd. Heat-developable photosensitive material
EP1041433A1 (en) * 1999-03-30 2000-10-04 Fuji Photo Film Co., Ltd. Heat-developable photosensitive material and method for forming image using the same
US6329127B1 (en) 1999-03-30 2001-12-11 Fuji Photo Film Co., Ltd. Heat-developable photosensitive material and method for forming image using the same
US6350569B1 (en) 1999-03-30 2002-02-26 Fuji Photo Film Co., Ltd. Heat-developable photographic material
US6316670B1 (en) 1999-07-19 2001-11-13 Fuji Photo Film Co., Ltd. Polyhalogenomethylsulfonyl compound
US6383731B2 (en) 1999-07-19 2002-05-07 Fuji Photo Film Co., Ltd. Polyhalogenomethylsulfonyl compound
US6368778B1 (en) 2000-08-15 2002-04-09 Eastman Kodak Company Photothermographic materials providing improved image stability and methods of use
US6506548B1 (en) * 2001-12-11 2003-01-14 Eastman Kodak Company Silver halide photographic materials containing solubilized antifoggants
US6514678B1 (en) 2001-12-11 2003-02-04 Eastman Kodak Company Photothermographic materials containing solubilized antifoggants
US6518007B1 (en) * 2001-12-11 2003-02-11 Eastman Kodak Company Silver halide elements containing solubilized antifoggants and low fogging tabular silver halide grains
US20040074847A1 (en) * 2002-10-16 2004-04-22 Jaquess Percy A. Stable N-bromo-2-pyrrolidone and methods to make the same
EP1582919A1 (en) 2004-03-23 2005-10-05 Fuji Photo Film Co. Ltd. Silver halide photosensitive material and photothermographic material
US7445884B2 (en) 2004-06-09 2008-11-04 Konica Minolta Medical & Graphic, Inc. Photothermographic material, development method and thermal development device thereof
US20060003272A1 (en) * 2004-06-09 2006-01-05 Konica Minolta Medical & Graphic, Inc. Photothermographic material, development method and thermal development device thereof
US20060014111A1 (en) * 2004-07-15 2006-01-19 Konica Minolta Medical & Graphic, Inc. Method of forming an image
US7267934B2 (en) 2004-07-15 2007-09-11 Konica Minolta Medical & Graphic, Inc. Method of forming an image
EP1635216A1 (en) 2004-09-14 2006-03-15 Fuji Photo Film Co., Ltd. Photothermographic material
WO2007010777A1 (ja) 2005-07-20 2007-01-25 Konica Minolta Medical & Graphic, Inc. 画像形成方法
EP1953592A1 (en) 2007-02-02 2008-08-06 Konica Minolta Medical & Graphic, Inc. Photothermographic material
US7468241B1 (en) 2007-09-21 2008-12-23 Carestream Health, Inc. Processing latitude stabilizers for photothermographic materials
US20090081578A1 (en) * 2007-09-21 2009-03-26 Carestream Health, Inc. Method of preparing silver carboxylate soaps
US7524621B2 (en) 2007-09-21 2009-04-28 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
US7622247B2 (en) 2008-01-14 2009-11-24 Carestream Health, Inc. Protective overcoats for thermally developable materials
WO2017123444A1 (en) 2016-01-15 2017-07-20 Carestream Health, Inc. Method of preparing silver carboxylate soaps

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FR2261555A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1975-09-12
DE2506815B2 (de) 1979-02-08
FR2261555B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1977-04-15
DE2506815A1 (de) 1975-08-28
BE825716A (fr) 1975-08-19
JPS50120328A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1975-09-20
JPS54165B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1979-01-08
GB1495335A (en) 1977-12-14
CA1045876A (en) 1979-01-09
DE2506815C3 (de) 1979-10-11

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