US3870523A - Heat developable photographic material containing azo dyes as sensitizers - Google Patents

Heat developable photographic material containing azo dyes as sensitizers Download PDF

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US3870523A
US3870523A US434453A US43445374A US3870523A US 3870523 A US3870523 A US 3870523A US 434453 A US434453 A US 434453A US 43445374 A US43445374 A US 43445374A US 3870523 A US3870523 A US 3870523A
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heat developable
developable photographic
photographic material
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Shinpei Ikenoue
Takao Masuda
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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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
    • G03C1/49854—Dyes or precursors of dyes

Definitions

  • ABSTRACT Heat developable photographic materials having at least one photosensitive layer on a support. This layer containing the following components:
  • Ar N NAr (1) sensitizing effect.
  • a photographic process using silver halides is the process which has heretofore been most widely utilized due to the. excellent photographic properties thereof, such as high sensitivity and good gradation over any of the other processes such as an electrophotographic process or a diazo-photographic process.
  • silver halide photographic materials used in this process are developed with a developer after image-wise exposure thereof, and then, they are subjected to several after-treatments such as stopping,f1xation, washing with water or stabilization so that the developed images are not discolored or deteriorated under normal light or so that the non-developed part (hereunder referred to as background) is not blackened. Accordingly, these treatments require time and labor.
  • a first method is the so-called one-bath development and fixation method as described in, for example, U.S. Pat. No. 2,875,048, British Pat. No. 954,453 and German Pat. No. 1,163,142, where the two operations of development and fixation in the conventional silver halide photographic process are carried out in one bath.
  • a second method is to try to change the wet-type treatment which has been employed in the present silver halide photographic process, to adry-type treatment, for example as described in German Pat. No. 1,174,159, British Pat. Nos. 943,476 and 951,644, etc.
  • a third method is to try to use, as photosensitive elements, a combination of a main component of a long chain aliphatic carboxylic acid silver salt such as silver behenate, or another silver salt such as silver saccharin or silver benzotriazole, and a catalytic amount of a silver halide, for example as described in Japanese Pat. Publication Nos. 26582/69 and 22185/70, British Pat. No. 1,205,500, and US. Pat. Nos. 3,152,904, 3,457,075, 3,635,719, and 3,645,739, etc.
  • This invention relates to the third approach among the above described three types of methods.
  • An object of this invention is to provide heat developable photographic materials having at least one sensitized light-sensitive layer.
  • the present inventors have conducted various research in an effort to obtain such sensitizers which are effective for heat developable photographic materials, and have at last found that the compounds of formulae (1) (II) as described herein have excellent sensitizing effects for the heat developable photographic materials of this invention.
  • This invention therefore relates to heat developable photographic materials having at least one layer on a support, which layer contains the following components:
  • Suitable aryl group represented by Ar,, Ar Ar and Ar,-, in the above formulae includes phenyl, oz-naphthyl and B-naphthyl groups, which can be unsubstituted or substituted.
  • Suitable arylene groups represented by Ar includes phenylene, biphenylene and naphthylene groups, which can be unsubstituted or substituted.
  • Suitable substituents of these aryl and arylene groups include alkyl groups (e.g., methyl groups, ethyl groups, t-butyl groups, etc), halogen atoms (e.g., chloride atoms, bromine atoms, iodine atoms), hydroxyl groups, SO;,M groups, -COOM groups, aryl groups (e.g., phenyl groups, tolyl groups, xylyl groups, etc.), nitro groups, amino groups, alkylamino groups, arylamino groups, acyl groups (e.g., acetyl groups, propionyl groups, etc.), alkoxy groups (e.g., methoxy groups, ethoxy groups, propoxy groups, etc.), arylsulfonyloxy groups, alkylsulfonyloxy groups, etc. as representative examples.
  • alkyl groups e.g., methyl groups, ethyl
  • alkyl, alkoxy and acyl groups suitably can have 1 to 8 carbon atoms, preferably l to 4 carbon atoms.
  • Preferred alkali metals are Li, Na, K, Pb, etc.
  • Preferred alkaline earth metals are Ca, Ba, Mg, etc. (1+)
  • the arylene group bonding can be at any position. Nao 5 Representative examples of preferred compounds of 3v this invention are as follows:
  • the amount of the component (e) which is added is suitably about 10' to 10 mole per 1 mole of the organic silver salt. This amount can be varied, depending upon the kind of the compound used, the kind of the organic silver salt, the kind of the catalytic amount of the silver halide, the kind of the reducing agent, the treating temperature, etc. If the amount of the component (e) exceeds the above described range, the degree of coloration of lightsensitive layer increases very often, which is disadvantageous in some uses. However, when the material is applied to such uses where coloration is not a problem or when compounds giving rise to less coloration are used as the component (e), the amount of the component (e) which can be used can exceed this range.
  • organic silver salts are suitable for use in the present invention, for example, the silver salts of organic compounds containing imino, mercapto or carboxyl groups, for example, as disclosed in US. Pat. Nos. 3,457,075 and 3,152,904.
  • organic silver salts are silver benzotriazole, silver saccharin, silver phthaladionone, the silver salt of 3-mercapto-4-phenyl-l,2,4- triazole, the silver salt or 4-hydroxy-6-methyl-l ,3,3a,7- tetrazaindene, the silver salt of Z-(S-ethylthioglycolamido)-benzothiazole, silver caprate, silver laurate, silver myristate, silver palmitate, silver stearate, silsver behenate, silver akipate, silver sebacate, etc.
  • the component (b) of the present invention is (la compound which reacts with the silver salt of the component (a) to form a silver halide, or is (2) a silver halide.
  • Representative examples of the compound (1 are inorganic compounds of the formula MX,,; where M represents a hydrogen atom, an ammonium group or a metal atom (such as strontium, cadmium, zinc, tin, chromium, sodium, barium, iron, cesium, lanthanum, copper, calcium, nickel, magnesium, potassium, aluminum, antimony, gold, cobalt, mercury, lead, beryllium, lithium, manganese, gallium, indium, rhodium, ruthenium, palladium, iridium, platinum, thallium, bismuth, etc.), X represents a halogen atom (such as chlorine, bromine, iodine),and when M is a hydrogen atom or an ammonium group n is l, but when M is a metal atom
  • organic halogen compounds such as triphenylmethyl chloride, triphenylmethyl bromide, 2-bromo-2-methylpropane, 2-bromobutyric acid, 2- bromoethanol, benzophenone dichloride, iodoformy carbon tetrachloride, etc. can also be included within the scope of compound(l).
  • Suitable silver halides of the latter (2) include silver chloride, silver bromide, silver iodobromide, silver iodobromochloride, silver bromochloride and silver iodide.
  • Suitable examples of components (b) above, are disclosed in US. Pat. No. 3,457,075.
  • the photosensitive silver halide can be in any form,
  • a suitable particle size can range from about 0.002 M to 2 u preferably 0.006 p. to 0.5 ,u.
  • the emulsion containing the photosensitive silver halide can be optionally prepared according to any of the methods which are known in the field of photography.
  • the emulsion can be prepared by the single-jet process, by the double-jet process, for example, a Lippmann emulsion, an ammonia process emul sion, a thiocyanate or thioether digested emulsion; for example, the emulsions as described in US. Pat. Nos. 2,222,264 and 3,320,069 and 3,271,157.
  • the silver halide which can used in this invention can be sensitized with conventional chemical sensitizers which are generally used for silver halide emulsions, for example, with reducing agents, sulfur or selenium compounds, gold, platinum or palladium compounds or a mixture thereof. Suitable methods for sensitization are described, for example, in US. Pat. Nos. 2,623,499; 2,399,083; 3,297,447 and 3,297,446.
  • the compound of the above described component (b) can be used alone or as a mixture of two or more kinds of compounds.
  • the amount of component (b) which can be added is suitably in the range of about 0.00] to 0.5 mole, preferably 0.01 to 0.2 mol, per 1 mole of organic silver salt. If the amount of the component (b) is lower than this range, the sensitivity of the material is reduced, but on the contrary, if the amount thereof exceeds this range, the presence of too large an amount of component (b) causes such an unfavorable phenomenon that when the material is left exposed to room light after the heat development thereof, the nonimage part gradually blackens, resulting in a decrease in the contrast between the non-image part and the image part.
  • the reducing agent of the component (c) of the present invention must be one suitable for the reduction of the organic silver salt to form silver images, when heated in the presence of the exposed silver halide catalyst.
  • a suitable reducing agent is determined in accordance-with the combination of the organic silver salt used, and, for example, substituted phenols, substituted or unsubstituted bisphenols, substituted or unsubstituted naphthols, dior poly-hydroxy benzenes, dior poly-hydroxy naphthalenes, hydroquinone monoethers, ascorbic acid or derivatives thereof, 3- pyrazolidones, pyrazol-S-ones, reducing sugars, kojic acid, hinokitiol, etc. can be rised.
  • Hydroquinone methylhydroquinone, chlorohydroquinone, bromohydroquinone, phenylhydroquinone, hydroquinone-monosulfonate, t-octylhydroquinone, t-butylhydroquinone, ,2,S-dimethylhydroquinone, 2,6-dimethylhydroquinone, methoxyhydroquinone, ethoxyhydroquinone, p-methoxyphenol, pethoxyphenol, hydroquinone-monobenzylether, catechol, pyrogallol, resorcin, p-aminophenol, o-
  • bisphenol A bisphenol A, l,1-bis-(2-hydroxy-3,S-dimethylphenyl)- 3,-5,5-trimethylhexane, 2,4,4-trimethylpentyl-bis-(2- hydroxy-3,S-dimethylphenyl)methane, bis(Z-hydroxy- 3-t-butyl-5-methylphenyl)-methane, bis(2-hydroxy- 4,4-methylenebis(3- methyl-S-t-butylphenol), 4,4'-methylenebis(2,6-di-tbutylphenol), 2,2'-methylenebis(2-t-butyl-4- ethylphenol), 2,6-dimethylenebis(2-hydroxy-3-t-butyldimethylamine, a,a'-(3,5-di-t-butyl-4-hydroxyphenyl)- dimethylether, etc.
  • reducing agents can be used in the form of a mixture of two or more of them.
  • a suitable reducing agent is selected in combination with the organic silver salt.
  • the higher fatty acid silver salts such as silver behenate are relatively difficultly reduced, and therefore relatively strong reducing agents, for example, the bisphenols such as 4,4'-methylenebis(3- methyl--t-butylphenol) are suitable therefor.
  • relatively weak reducing agents for example, the substituted phenols such as p-phenylphenol, are suitable for silver salts which are relatively easily reduced, such as silver laurate.
  • strong reducing agents such as ascorbic acid type reducing agents are suitable for silver salts which are extremely difficultly reduced, such as silver benzotriazole.
  • the amount of reducing agent which is used in this invention as described above will vary depending upon the organic silver salt used and the kind of reducing agent used, and therefore, the amount cannot unequivocally set forth, but in general, the amount suitably ranges from about 0.1 to 5 moles, preferably 0.6 to 2 moles per 1 mole of organic silver salt.
  • an appropriate reducing agent can be selected and used in combination with a specific organic silver salt, and therefore it is unnecessary to specifically define the organic silver salt and reducing agent used.
  • the components (a), (b), (c) and (e) are preferably dispersed in a binder and applied on a support.
  • all of the components (a) to (e) are completely dispersed in the binder and applied on a support as one layer, or alternatively, these components (a) to (e) can be separated into groups and dispersed separately in the binder and then the respective dispersions are applied on a support as individual layers.
  • the binder component (d) any and every conventional binder which has heretofore been used in this field can be used. In general, hydrophobic binders are preferred, but hydrophilic binders can also be used.
  • binders are preferably transparent or semi-transparent, and suitable binders are, for example, natural substances, such as gelatin, gelatin derivatives or mixtures thereof with latex type vinyl polymers, cellulose derivatives, and synthetic polymer sub-- stances, etc.
  • binders are as follows: gelatin, gelatin phthalide, acrylamide, polyvinyl butyral, cellulose acetate-butyrate, cellulose acetatepropionate, polymethylmethacrylate', polyvinyl pyrrolidone, polystyrene, ethyl-cellulose, polyvinyl chloride, chlorinated rubber, polyisobutylene, butadienestyrene copolymers, vinyl chloride-vinyl acetate copolymers, vinyl acetate-vinyl chloride-maleic acid copolymers, polyvinyl alcohol, polyvinyl acetate, benzyl cellulose, cellulose acetate, cellulose propionate, cellulose acetate-phthalate, etc.
  • the amount of binder is suitably in a ratio (by weight) of about 0.1:1 to 5:1,preferably 0.2:1 to 3:1 on the basis of the amount of the organic silver salt.
  • the component (a) or (c) is a high molecular weight substance which has the function of a binder, the use of binder can be omitted.
  • supports in a broad range can be used.
  • Representative supports are, for example, cellulose nitrate films, cellulose ester films, poly(- vinylacetal) films, polystyrene films, poly(ethyleneterephthalate) films, polycarbonate films, and glass, paper, metal, etc. supports a suitable coating amo unt ranges from 0.1 to 3 g/m preferably 0.3 to 2 g/m
  • An antistatic layer or a conductive layer can be provided in the heat developing photographic materials of this invention.
  • an anti-halation material and an anti-halation dye can also be incorporated therein.
  • the heat developable photographic materials of this invention can optionally contain matting agents such as starch, titanium dioxide, zinc oxide and silica.
  • matting agents such as starch, titanium dioxide, zinc oxide and silica.
  • fluorescent whitening agents such as stilbene, triazine, oxazole, and coumarin type fluorescent whitening agents can also be contained therein.
  • the heat developable photosensitive layer(s) of this invention can be applied to a support using various coating methods, for example, the dip method the airknife method, the curtain coating method as well as the extrusion coating method with a hopper as described in US. Pat. No. 2,681,294. If necessary, two or more layers can be simultaneously applied.
  • optical sensitizing dyes which have heretofore been used for silver halide emulsions can advantageously be used in the heat developing-out photographic material of the present invention for imparting additional sensitivity thereto.
  • the cyanine dyes and merocyanine dyes as disclosed in US. Pat. Nos. 3,457,075 and 3,761,279, are suitable as the optical sensitizing dyes which can be used in the present invention.
  • . 2 5 ca-ca n N x (L S H 2 5 C 11 s l k a 0 N S C 11 v 7 2% s (1 011 on s N l A 1 o n s C H 11 CH N N (Hi-CRT- S o u /L 5 ll N ⁇ N developable photographic material.
  • the thickness of this over-coating polymer layer film is suit- 5 S ably 1 to 20 .1..
  • Suitable polymers for this layer are, for example, as T follows: polyvinyl chloride, polyvinyl acetate, vinyl C 11 chloridevinyl acetate copolymers, polyvinyl butyral,
  • polystyrene polymethylmethacryate
  • polyurethane 2 5 5 rubbers polyurethane 2 5 5 rubbers
  • xylene resins polystyrene, polymethylmethacryate, polyurethane 2 5 5 rubbers, xylene resins, .benzylcellulose, ethyl cellulose,
  • the tem- L H c H perature generally employed in the heating is suitably 2 5 2 5 in the range of 100 to 160C, more preferably 110 to 140C.
  • the time for the development is in general about 1 to 60 seconds. Higher temperatures or lower temperatures can be selected within the above described range, by prolonging or reducing the heating time.
  • the photographic material can be brought into contact with a simple hot plate or the like,
  • s or can be brought into contact with a heated drum, or as the case may be, can also be passed through a heated f .zone.
  • high frequency induction heating or ON laser beam heating can also be utilized.
  • sensitizing dyes are preferably added to photographic materials in the form of a solution or dispersion dissolved or dispersed in an organic solvent.
  • the use of the optical sensitizing dye together with the sensitizer component (e) of this invention causes an increase of sensitivity of the resulting heat.
  • EXAMPLE 1 3.4 g of behenic acid were dissolved in ml of toluene at 60C and the resulting solution was adjusted to 60C. While stirring with a stirrer, 100 ml of a diluted nitric acid aqueous solution (pH 2.0 at 25C) were added and mixed therewith.
  • the resulting mixture solution was kept at 60C, and while continuously stirring with a stirrer, an aqueous solution containing a silverammonium complex is added thereto.
  • This complex solution was prepared as follows. Aqueous ammonia was added to about 80 ml of an aqueous solution containing 1 .7 g of silver nitrate to form a silver-ammonium complex, and water was added thereto to make the total volume of the aqueous solution 100 ml.) Thus, a dispersion containing fine crystals of silver behenate was obtained. This dispersion was left at room temperature (about C) for 20 minutes, whereby an aqueous layer and a toluene layer were separated from each other.
  • each of these photographic materials (A) (C) was further over-coated a 15 wt percent tetrahydro-furan solution of a vinyl chloride-vinyl acetate copolymer (consisting of 95 wt percent of vinyl chloride and 5 wt percent of vinyl acetate), to form a over-coating film of a thickness of 10 ,u (after drying).
  • a vinyl chloride-vinyl acetate copolymer consisting of 95 wt percent of vinyl chloride and 5 wt percent of vinyl acetate
  • EXAMPLE 2 In this Example, the same amount of merocyanine dye of Example 1 was used together with Compound (3), in place of the use of Compound (3) only, and others materials were the same as in Example 1.
  • Material Material Material Material B (C Relative Sensitivity 9,300 100 600 The effect of the present sensitizer is similar to that of the Example 1.
  • EXAMPLE A solution of l l g of lauric acid dissolved in 100 ml of isoamyl acetate was kept at 5C, and, while stirring, 100 ml of a diluted nitric acid aqueous solution (pH 2.0 at 25C) were added thereto and admixed, and then while further continuously stirring, 50 ml of a silver nitrate-ammonium complex aqueous solution containing 8.5 g of silver nitrate were added thereto over the course of 1 minute thereby to react the lauric acid and silver ion.
  • Theaqueous phase wasfirst removed, and 400 ml of water were added again to the remaining phase to wash the same by the decantation method. This operation was repeated three times, and then 400 ml of methanol were added to separate the silver benzotriazole by centrifuging. Thus, .8 g of silver benzotriazole were obtained.
  • the particles of the silver benzotriazole were of a nearly spherical form, having a particle size diameter of about 1 u.
  • a heat developable photographic material having at least one photosensitive layer on a support, said layer containing the following components:
  • Ar Ar and Ar,- each represents an aryl group and Ar, represents an arylene group, with the proviso that at least one of Ar, and Ar and at least one of Ar;,, Ar and Ar is substituted with a SO M group.
  • M being a hydrogen atom, an alkali metal atom, an alkaline earth metal atom, or a Nl-l, group.
  • sensitizer (e) is selected from the group consisting of the following com-. pounds coon NaO S COONa SO Na Mao;
  • optical sensitizing dye is a cyanine dye or a merocyanine dye.

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  • Chemical & Material Sciences (AREA)
  • 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)
US434453A 1973-01-17 1974-01-17 Heat developable photographic material containing azo dyes as sensitizers Expired - Lifetime US3870523A (en)

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JP (1) JPS4996717A (enrdf_load_stackoverflow)
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FR (1) FR2324025A1 (enrdf_load_stackoverflow)
GB (1) GB1424643A (enrdf_load_stackoverflow)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2379833A1 (fr) * 1977-02-07 1978-09-01 Eastman Kodak Co Produit photographique thermodeveloppable
US4128428A (en) * 1974-04-10 1978-12-05 Fuji Photo Film Co., Ltd. Heat developable light-sensitive material
US4142901A (en) * 1976-11-12 1979-03-06 Eastman Kodak Company Photographic materials comprising azo sensitizing dyes
US4173478A (en) * 1977-10-28 1979-11-06 Eastman Kodak Company Photographic materials comprising azo sensitizing dyes
US4187108A (en) * 1977-02-07 1980-02-05 Eastman Kodak Company Heat developable material and process
US4207108A (en) * 1976-11-04 1980-06-10 Eastman Kodak Company Silver halide photothermographic element, composition and process
US4237213A (en) * 1976-01-30 1980-12-02 Canon Kabushiki Kaisha Image forming method

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5151933A (ja) * 1974-11-01 1976-05-07 Fuji Photo Film Co Ltd Netsugenzokankozairyo

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3457075A (en) * 1964-04-27 1969-07-22 Minnesota Mining & Mfg Sensitized sheet containing an organic silver salt,a reducing agent and a catalytic proportion of silver halide
US3645739A (en) * 1966-02-21 1972-02-29 Fuji Photo Film Co Ltd Thermally developable light-sensitive elements
US3700457A (en) * 1970-04-09 1972-10-24 Eastman Kodak Co Use of development inhibitor releasing compounds in photothermographic elements
US3770448A (en) * 1970-04-29 1973-11-06 Agfa Gevaert Ag Lightsensitive photographic material

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3457075A (en) * 1964-04-27 1969-07-22 Minnesota Mining & Mfg Sensitized sheet containing an organic silver salt,a reducing agent and a catalytic proportion of silver halide
US3645739A (en) * 1966-02-21 1972-02-29 Fuji Photo Film Co Ltd Thermally developable light-sensitive elements
US3700457A (en) * 1970-04-09 1972-10-24 Eastman Kodak Co Use of development inhibitor releasing compounds in photothermographic elements
US3770448A (en) * 1970-04-29 1973-11-06 Agfa Gevaert Ag Lightsensitive photographic material

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4128428A (en) * 1974-04-10 1978-12-05 Fuji Photo Film Co., Ltd. Heat developable light-sensitive material
US4237213A (en) * 1976-01-30 1980-12-02 Canon Kabushiki Kaisha Image forming method
US4207108A (en) * 1976-11-04 1980-06-10 Eastman Kodak Company Silver halide photothermographic element, composition and process
US4142901A (en) * 1976-11-12 1979-03-06 Eastman Kodak Company Photographic materials comprising azo sensitizing dyes
FR2379833A1 (fr) * 1977-02-07 1978-09-01 Eastman Kodak Co Produit photographique thermodeveloppable
US4187108A (en) * 1977-02-07 1980-02-05 Eastman Kodak Company Heat developable material and process
US4173478A (en) * 1977-10-28 1979-11-06 Eastman Kodak Company Photographic materials comprising azo sensitizing dyes

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JPS4996717A (enrdf_load_stackoverflow) 1974-09-12
FR2324025B1 (enrdf_load_stackoverflow) 1978-03-10
FR2324025A1 (fr) 1977-04-08
GB1424643A (en) 1976-02-11
DE2401982A1 (de) 1974-07-18

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