US3775128A - Silver halide emulsion containing a triazine as antifoggant - Google Patents

Silver halide emulsion containing a triazine as antifoggant Download PDF

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Publication number
US3775128A
US3775128A US00282094A US3775128DA US3775128A US 3775128 A US3775128 A US 3775128A US 00282094 A US00282094 A US 00282094A US 3775128D A US3775128D A US 3775128DA US 3775128 A US3775128 A US 3775128A
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United States
Prior art keywords
photographic
silver halide
emulsion
compound
added
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Expired - Lifetime
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US00282094A
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English (en)
Inventor
N Yamamoto
Y Minagawa
T Sueyoshi
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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
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/81—Photosensitive materials characterised by the base or auxiliary layers characterised by anticoiling means
    • 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
    • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression

Definitions

  • ABSTRACT wherein R R and R each represents a hydrogen atom or an alkyl group substituted by a hydroxyl group, wherein R R and R are not simultaneously a hydrogen atom, is disclosed.
  • the present invention relates to a silver halide lightsensitive material. More particularly, it relates to a silver halide photographic light-sensitive material wherein fog formation and curling tendency are reduced by an improvement in the physical properties thereof.
  • a silver halide photographic emulsion is prepared using a high molecular weight material such as gelatin, polyvinyl alcohol, etc., as a protective colloid and dispersing the crystals of silver iodide, silver bromide or silver chloride, or the mixed crystals thereof in the protective colloid.
  • a high molecular weight material such as gelatin, polyvinyl alcohol, etc.
  • Photographic printing papers, dry plates, films, etc. are prepared by applying such a silver halide photographic emulsion in the form of a thin film to a support such as a synthetic high polymer-laminated paper, glass, cellulose ester, or synthetic high molecular film, e.g., polyethylene terephthalate, etc.
  • a support such as a synthetic high polymer-laminated paper, glass, cellulose ester, or synthetic high molecular film, e.g., polyethylene terephthalate, etc.
  • Silver halide emulsion-coated materials obtained by applying the emulsion to various supports and drying as described above are known to undergo an undesirable photographic change referred to as kink desensitization or kink fog when a mechanical stress is exerted externally thereon momentarily or for a short time.
  • kink desensitization or kink fog undesirable photographic change
  • kink fog undesirable photographic change
  • kink fog undesirable photographic change
  • the defects in that the physical properties of the silver halide photographic emulsion-coated materials when left under high temperature and high humidity are not sufficiently improved, that adverse effects on the photographic properties, such as fogging and desensitization are brought about, in that the curl-reducing effect is poor although deterioration in photographic properties due to the mechanical stress is prevented to some extent, or in that, although the curling tendency is suppressed to some extent, the surface of the coated material is too tacky resulting in adhesion to other surfaces have occurred.
  • This phenomenon is a newly found phenomenon and is different from the previously known kink fog or kink desensitization caused by bending the element sharply for a short period of time in that the former occurs when a photographic light-sensitive material is kept in a kink or curved condition for a comparatively long period of time.
  • the deterioration in photographic properties caused by maintaining the silver halide emulsion-coated material in the above-described state will spoil the practical value of the photographic lightsensitivematerial.
  • An object of this invention is to provide a method for effectively controlling the curling of a silver halide photographic layer applied to a support without degrading the other physical and photographic properties thereof.
  • Another object of the invention is to provide a method for preventing fog formation or desensitization which is caused by leaving the silver halide photographic light-sensitive material for a long period of time in a kinked or bent state, without degrading the other physical and photographic properties thereof.
  • R, R and R each represents a hydrogen atom or an alkyl group substituted by hydroxyl group, wherein R R and R are not simultaneously a hydrogen atom.
  • FIGURE illustrating the bending stress-fog test, wherein I, II, and III designate an emulsion layer, a support and a cylinder made of iron, respectively.
  • alkyl group as used herein is intended to include alkyl groups containing hetero atoms (for example, an oxygen atom) in the carbon chain as well.
  • hetero atoms for example, an oxygen atom
  • substituted alkyl group for R R or R CH-,CH OH, CH CH OCH OH or -CH1CHCH3 is preferred.
  • the above-illustrated compounds which can be used in the invention are hydrophilic compound which are soluble in water in high concentrations, but have such a small hygroscopic property that the coated photographic layer containing these compounds cause less sticking to other surfaces in comparison with the coated photographic layer to which the known hydrophilic compounds are added. Therefore, no difficulty in that the amount thereof added must be restricted due to the tackiness resulting occurs.
  • the compounds are usually added in an amount of from 0.1 to 30 percent by weight (hereinafter all percents are by weight) based on the amount of silver contained in the silver halide photographic emulsion.
  • a silver halide photographic coated material to which the compounds are added at a level ranging from 0.5 to 20 percent not only is desensitization, fog formation and curling tendency of the material occurring when a mechanical bending stress is exerted thereon for a long period of time markedly controlled, but also the tackiness of the surface of the coated material can be maintained at a far lower level than when other known gelatin plasticizers are added.
  • the compounds may be added in an amount outside the abovedescribed range. However, the addition of less than 0.1 percent of the compounds is not sufficient to obtain sufficient effects, while the addition above 30 percent does not further enhance the effect and it is therefore disadvantageous from the viewpoint of cost. Two or more of these compounds may be used in combination. In addition, these compounds may be used together with a suitable amount of other known photographic hydrophilic compounds.
  • the point at which the compounds used in the invention are incorporated in a photographic emulsioncoated material is not particularly limited, but incorporation between the after-heating step of the silver halide emulsion and the step of coating and drying is pref- I erable.
  • they can be added as a solution of the solvent exerting no adverse effects on a silver halide photographic emulsion, such as water, a lower alcohol (e.g., methanol, ethanol, isopropanol, etc.), etc.
  • the photographic coated layer containing the compounds of the invention can be a photographic emulsion layer containing silver halide, a layer adjacent to the silver halide photographic emulsion layer, such as a protective layer or a intermediate layer in the photographic light-sensitive material, or can be a combination thereof.
  • a layer adjacent to the silver halide photographic emulsion layer such as a protective layer or a intermediate layer in the photographic light-sensitive material
  • the addition of the compound of the invention to only one layer of the layers constituting the material can provide the other layers with the effect of preventing fogging due to pressure through the diffusion effect.
  • the present invention can be applied to various silver halide photographic emulsions used in photography such as silver chloride,.silver bromide, silver iodide, silver iodobromide, silver chlorobromide, silver iodochlorobromide, etc.
  • the emulsion can be used in conventional black and white and color photographic materials as well as those used in a diffusion transfer process and a silver dye bleach process.
  • dispersion medium for a photographic emulsion
  • gelatin coloidal albumin, collodion, gum arabic
  • agar-agancellulose derivatives e.g., alkyl esters of carboxylated cellulose such as hydroxyethyl cellulose, carboxymethyl hydroxyethyl-cellulose, etc.
  • synthetic resins e.g., polyvinyl alcohol, polyvinyl pyrrolidone, etc.
  • The'photographic emulsion is applied to various supports such as a cellulose ester film, a polyvinyl acetal film, a polyethylene'jfierephthalate film, a polystyrene film, a paper, a polyethylene-laminated paper, a paper substitute, and the like.
  • the silver halide photographic emulsion employed in the invention may be sensitized with the chemically sensitizing agents, spectrally sensitizing agents, polyalkylene oxide derivatives, etc. known in the art, or by the combined use thereof.
  • the photographic emulsion layer may be stabilized by the addition of various anti-foggants, stabilizers, etc. known in the art, or may be hardened with various known photographic hardeners.
  • coating agents well known in the art such as natural surface active agents (e.g., saponin), nonionic surface active agents,
  • anionic surface active agents cationic surface active.
  • the photographic emulsion layer and the adjacent'layers may be added a photographic water-dispersingvinyl poly-v mer well known in the art.
  • the surface layer of the silver halide photographic light-sensitive material of the invention may be subjected to a static charge-preventing processing using various kinds of antistatic agents.
  • EXAMPLE 1 A gelatino-silver bromoiodide photographic emulsion of a mean grain size of 0.35 p. containing 0.6 mol percent of silver iodide was prepared in a conventional manner. The composition by weight of the major components in the photographic emulsion was percent of silver halide, 6 percent of gelatin and 69 percent of water, to which suitable amount of saponin as a coating aid and mucochloric acid as a hardening agent had been added.
  • coating solutions B,C,D and E 100 grams of the photographic emulsion were removed, and 1 ml or 3 ml of a 25 percent aqueous solution of compound (2) or compound (3) (described hereinbefore) of the invention was added to each of the emulsions to prepare coating solutions B,C,D and E.
  • coating solutions F and G were prepared by adding 1 ml or 3 ml ofa 25 percent aqueous solution of a conventional gelatin plasticizer, 1,2,4 -butanetriol, to the above-described photographic emulsion.
  • a coating solution A to which neither the compound of the invention nor 1,2,4 -butanetriol was added was prepared.
  • the resulting photographic emulsion coating solutions of A to G were applied to a subbed support of polyethylene terephthalate film of a thickness of 180 p. in an amount of 6 ml/ 100 cm and then dried under the conditions of a temperature of 23C, a relative humidity of 75 percent and a wind velocity of 1.5 m/sec.
  • the photographic films thus obtained were slit into pieces of 3 mm in width x mm in length.
  • the strips were left for 24 hours under the conditions of a temperature of 23C and a relative humidity of percent, with one end of the strips being stationarily fixed, and the distance of the movement of the other end due to the curling phenomenon caused by the contraction of the photographic emulsion layer was measured to examine thereby the degree of curling.
  • EXAMPLE 2 The same silver bromoiodide photographic emulsion A as described in Example 1 was applied to a polyethylene terephthalate support of a thickness of 180 having thereon a subbing layer in a silver amount of 50 mg/ cm and dried, to which a 5 percent gelatin aqueous solution containing the following additives was applied in such an amount per unit area (100 cm") that the following samples H,l,.l and K were prepared, and dried to prepare the four kinds of double-layer coated photographic films.
  • sample I to which compound (3) of the invention was added showed remarkably less curling tendency in comparison with sample H to which nothing was added and sample J to which a convent onal gelatin plasticizer, 1,6 -hexanediol, was added.
  • sample K in which the compound of the invention and the conventional plasticizer were used in combination so that they were incorporated in the coating composition in the same ratio by weight the curling tendency was markedly controlled in comparison with sample 1.
  • sample adhesion between the coated surface and the back surface of the film partially resulted for sample J, whereas sample K in accordance with the invention had only a slight amount of adhesion phenomenon and, in sample I, no adhesion phenomenon appeared similar to sample H to which nothing had been added.
  • EXAMPLE 3 A red sensitive photographic emulsion was prepared as follows. To 1000 g of a negative silver bromoiodide emulsion containing 4.5 g of silver bromoiodide (containing 6.0 mol percent of silver iodide) per 100 g of the emulsion and 16 g of gelatin were successively added the following additives: 90 g of a DJ percent methanol solution of a spectrally sensitizing agent (a) g of a 1 percent aqueous solution of S-methyl- 7-hydroxy-2,3,4 triazaindolizine and 450 g of cyan coupler emulsion prepared according to the following composition;
  • the red sensitive color emulsion thus obtained was divided into four equal portions, and to each portion was added 10 g of a 30 percent aqueous solution of compound (1) of the invention, compound (2) of the invention or compound (3) of the invention, or 10 g of water for comparison.
  • Each of the above-described emulsions was applied to a subbed support of cellulose triacetate in a dry thickness of 5 p.
  • Second Fixation (20C, 5 minutes) The same formulation as in the first fixation. 8. Washing (20C, 20 minutes) The fog density of each photographic film sample at the portion closely superposed on the cylindrical part was measured through a red filter, the sample having been subjected to the bending stress and then photo- -9 graphically processed. The results obtained are given in Table. 4.
  • EXAMPLE 4 In order to compare samples P and Q to which compounds (3) and (4) of the invention were added, respectively, with samples R and S to which a conventional compound, glycerin or 1 ,1 1 trimethylolpropane, reported to be effective for the socalled kink desensitization or kink fog was added, samples P to S of fourphoto'graphic films were prepared in the same manner as described in Example 3 except that 3 ml of a 25 percent aqueous solution of each of four compounds was added per 100 g of the emulsion, and then the bending stress-fog test was conducted.
  • Trimethylolpropane 0.64 35 As is apparent from the results contained in Table 5 above, sample S to which 1,1,l-trimethy1olpropane had been added exhibited almost no fog-controlling effect although there was no problem in the adhesive properties thereof, and sample R to which glycerin had been added showed the defect that the adhesive properties of the surface of the emulsion layer was degraded although a fog-controlling effect was obtained. On the contrary, it can be seen that, for samples P and Q to which the compounds of the present invention had been added, fog was markedly controlled without degrading the adhesive properties.
  • EXAMPLE 5 A red sensitive photographic emulsion obtained in the same manner as described in Example 3 was divided into four equal portions, and-to each portion was added 10 g of a 30 percent aqueous solution of compound (5) or (6) of the invention, or of the conventional compound, l,4-cyclohexanedimethanol, for comparison, instead of the compounds (1 (2) and (3) added in Example 3, or 10 g of water for comparison without an additive.
  • each of the above-described red sensitive photographic emulsions was applied to a subbed support in a dry thickness of 5p.
  • To each of the red sensitive emulsion-coated films thus obtained were successively applied the following coating layer, then dried to prepare thereby multi-layer color film samples T, U, V and W.
  • a green sensitive photographic emulsion layer the following photographic emulsion (c) was applied in a dry thickness of 4.5;;.. v
  • the green sensitive photographic emulsion (c) was prepared as follows. That is, to 1000 g of a negative silver bromoiodide emulsion containing 8 g of silver bromoiodide (containing 6.0 mol percent of silver iodide) per 100 g of the emulsion and 12 g of gelatin were added successively the following additives at 40C; 150 g of a 0.1 percent methanol solution of a spectrally sensitizing agent (e) 20 g of a 1 percent aqueous solution of S-methyl- 7-hydroxy- 2,3,4-triazaindolizine and 450 g of a magenta coupler emulsion prepared according to the following formulation;
  • the blue sensitive photographic emulsion (d) was prepared as follows. To 1000 g of a negative silver bromoiodide emulsion containing 4.5 g of silver bromoiodide (containing 6.0 mol percent of silver iodide) per 100 g of the emulsion and 16 g of gelatin were added 5 successively the following additives at 40C: 20 g of a 1 percent aqueous solution of S-methyl- 7-hydroxy- 2,3,4-triazaindolizine and 500 g of a yellow coupler emulsion prepared according to the following formulation;
  • R R and R each represents a hydrogen atom or an alkyl group substituted by a hydroxyl group wherein R R and R are not simultaneously a hydrogen atom, said compound being present in an amount of at least 0.] percent by weight based on the amount of silver present.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US00282094A 1971-08-25 1972-08-21 Silver halide emulsion containing a triazine as antifoggant Expired - Lifetime US3775128A (en)

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JP46064990A JPS505049B2 (enrdf_load_stackoverflow) 1971-08-25 1971-08-25

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US (1) US3775128A (enrdf_load_stackoverflow)
JP (1) JPS505049B2 (enrdf_load_stackoverflow)
DE (1) DE2241400A1 (enrdf_load_stackoverflow)
FR (1) FR2150504B1 (enrdf_load_stackoverflow)
GB (1) GB1362120A (enrdf_load_stackoverflow)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4021249A (en) * 1974-09-12 1977-05-03 Fuji Photo Film Co., Ltd. Heat developable light-sensitive material incorporating a substituted s-triazine-2,4,6-(1H, 3H, 5H)-trione reducing agent
US4126472A (en) * 1974-02-24 1978-11-21 Fuji Photo Film Co., Ltd. Process of making a lithographic photosensitive silver halide emulsion having reduced susceptibility to pressure containing an iridium compound, a hydroxytetrazaindene and a polyoxyethylene
EP0239363A2 (en) 1986-03-25 1987-09-30 Konica Corporation Light-sensitive silver halide photographic material feasible for high speed processing
USH874H (en) * 1986-06-04 1991-01-01 Konishiroku Photo Industry Co., Ltd. Process for manufacturing a silver halide photographic material having a support and at least one hydrophilic colloid layer
US5057548A (en) * 1986-08-08 1991-10-15 Krauss-Maffei A.G. Impingement mixing apparatus
US20080199744A1 (en) * 2007-02-21 2008-08-21 Samsung Electro-Mechanics Co., Ltd. Hydrogen generating apparatus, fuel cell power generation system, method of controlling hydrogen generating quantity and recorded medium recorded program performing the same
US20080241610A1 (en) * 2007-03-16 2008-10-02 Samsung Electro-Mechanics Co., Ltd. Hydrogen generating apparatus and fuel cell power generation system controlling amount of hydrogen generation

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7408591B2 (ja) * 2021-03-22 2024-01-05 四国化成工業株式会社 カルボキシル基を有するイソシアヌレート化合物および該化合物を用いたエポキシ樹脂組成物

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2586168A (en) * 1947-07-11 1952-02-19 Gen Aniline & Film Corp Process of hardening gelatin and photographic gelatin emulsions
US2708162A (en) * 1954-04-29 1955-05-10 Eastman Kodak Co Urazole stabilizer for emulsions sensitized with alkylene oxide polymers

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2586168A (en) * 1947-07-11 1952-02-19 Gen Aniline & Film Corp Process of hardening gelatin and photographic gelatin emulsions
US2708162A (en) * 1954-04-29 1955-05-10 Eastman Kodak Co Urazole stabilizer for emulsions sensitized with alkylene oxide polymers

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4126472A (en) * 1974-02-24 1978-11-21 Fuji Photo Film Co., Ltd. Process of making a lithographic photosensitive silver halide emulsion having reduced susceptibility to pressure containing an iridium compound, a hydroxytetrazaindene and a polyoxyethylene
US4021249A (en) * 1974-09-12 1977-05-03 Fuji Photo Film Co., Ltd. Heat developable light-sensitive material incorporating a substituted s-triazine-2,4,6-(1H, 3H, 5H)-trione reducing agent
EP0239363A2 (en) 1986-03-25 1987-09-30 Konica Corporation Light-sensitive silver halide photographic material feasible for high speed processing
USH874H (en) * 1986-06-04 1991-01-01 Konishiroku Photo Industry Co., Ltd. Process for manufacturing a silver halide photographic material having a support and at least one hydrophilic colloid layer
US5057548A (en) * 1986-08-08 1991-10-15 Krauss-Maffei A.G. Impingement mixing apparatus
US20080199744A1 (en) * 2007-02-21 2008-08-21 Samsung Electro-Mechanics Co., Ltd. Hydrogen generating apparatus, fuel cell power generation system, method of controlling hydrogen generating quantity and recorded medium recorded program performing the same
US20110104579A1 (en) * 2007-02-21 2011-05-05 Samsung Electro-Mechanics Co., Ltd. Fuel cell power generation system, method of controlling hydrogen generating quantity and recorded medium recorded program performing the same
US20080241610A1 (en) * 2007-03-16 2008-10-02 Samsung Electro-Mechanics Co., Ltd. Hydrogen generating apparatus and fuel cell power generation system controlling amount of hydrogen generation

Also Published As

Publication number Publication date
FR2150504B1 (enrdf_load_stackoverflow) 1976-08-13
GB1362120A (en) 1974-07-30
JPS4830921A (enrdf_load_stackoverflow) 1973-04-23
FR2150504A1 (enrdf_load_stackoverflow) 1973-04-06
DE2241400A1 (de) 1973-03-01
JPS505049B2 (enrdf_load_stackoverflow) 1975-02-27

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