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US2131038A - Photographic emulsion containing alkyl quaternary salts of thiazoles and the like asantifoggants - Google Patents

Photographic emulsion containing alkyl quaternary salts of thiazoles and the like asantifoggants Download PDF

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Publication number
US2131038A
US2131038A US67171933A US2131038A US 2131038 A US2131038 A US 2131038A US 67171933 A US67171933 A US 67171933A US 2131038 A US2131038 A US 2131038A
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group
alkyl
emulsion
containing
anti
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Leslie G S Brocker
Cyril J Staud
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Eastman Kodak Co
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Eastman Kodak Co
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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/005Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/34Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression

Description

Patented Sept. 27, 1938 UNITED STATES PATENT OFFICE PHOTOGBAPHIO EMULSION CONTAINING ALKYL QUATERNARY SALTS F THIA- ZOLES AND THE LIKE AS ANTIFOGGANTS Kodak Company, Jersey City, N. J.,

a corporation of New Jersey No Drawing. Application May 18, 1933, Serial No. 671,718. Renewed October 14, 1936.

Great Britain May 26, 1932 130laims.

This invention relates to anti-fogging agents for photographic emulsions, such as gelatino-silver-halide'emulsions, and more particularly to the use of alkyl quaternary salts of oxazoles, se-

6 lenasoles and thiazoles for that purpose.

Some sensitizing dyes, while being powerful color sensitizers, have a fogging action upon photographic emulsions containing them. It is also well known that when development of photo- 10 graphic film is continued for protracted periods, or at temperatures above normal, log is apt to result.

We have found that these harmful eflects can be decreased by adding a small proportion of one or more of the above heterocyclic compounds to l photographic emulsions.

An object of our invention, therefore, is to provide photographic emulsions of enhanced stability. Other objects will hereinafter appear.

We have discovered that alkyl quaternary salts 20 containing the nucleus Y i 25 where Y=O, 8 or Be may be used as stabilizing agents in the above sense.

Certain cyanine dyes containing the above nucleus exert a stabilizing or anti-fogging effect in addition to a specific color-sensitizing action.

30 For instance, when 1,1-diethylthiocarbocyanine iodide is used in conjunction with pinacyanol (1,1'-diethyl-2,2'-carbocyanine iodide), definite improvement in stability results. Such dyes, however, cannot be used if the color sensitiveness 35 which they confer is undesirable, but we have found that certain other compounds containing the above nucleus are eflectlve while at the same time not exerting a color-sensitizing action.

In general, the most eilective compounds are 40 salts containing the nucleus, specifically known as alkyl quaternary salts of the type.

R/ x where Y=O, S or Se 50 R=alkyl X=an acid radical A=a monovalent atom or grouping, such as hydrogen, alkyl, or aryl, and

D=vinylene, ethylene, phenylene, naphthylene,

etc.

Of these compounds, the most valuable are those in which Y=suliur or selenium. These salts, then are alkyl quaternary salts of thiazoline or selenazoline or of thiazole or selenazole bases. The

tendency to reduce fog is noticeable in some of the parent bases but, in general, the effect is much thiazoles (naphthoselenazoles) or the like. Any

of these rings may be substituted in positions where this is possible. For instance, the carbon atom situated between the two hetero atoms, and commonly known as the mu-carbon atom, may be linked to hydrogen, to alkyl, or to aryl. Examples of all these types will follow.

In anti-fogging effect, these quaternary salts vary greatly, as would be expected. The most useful of them are such as show a pronounced effect while causing relatively slight loss in sensitivity, although others desensitize somewhat more noticeably besides diminishing the fog. This desensitization, however, does not nullify their utility as anti-foggants. The eil'ect also varies with the type of emulsion used, so that one agent. is perhaps indicated for one emulsion, while another is better for a second emulsion.

In practice it has been found suitable to add only a very small amount of the anti-fogging agent to the emulsion just prior to coating. The amount varies, but on an average 2-8 mg. are added, in solution, to 100 cc. of a photographic emulsion containing sensitizers, if desired, such as is known to those skilled in the photographic art. Obviously more can be used where a badly fogging emulsion has to be corrected.

Examples The base 2-methylthiazoline shows a distinct tendency to reduce photographicfog. 2-methylthiazoline methiodide, however, shows this property to an enhanced degree. With 2,4-dimethylthiazole, the effect is not so pronounced but the ethiodide of the base shows the effect, although not particularly strongly. 2-methyl-4-phenylthiazole methiodide shows the effect but also causes excessive desensitization.

The base l-methylbenzothiazole only has a slight eifect, but its methiodide is very efiective. Similarly, l-methylbenzothiazole metho p-toluenesulfonate is quite powerful, and so are the etho-petoluenesulfonate, ethiodide and alliodide of 1 -methylbenzothiazole. The methiodide and ethiodide of benzothiazole itself are also very effective.

l-methyl-5-ethoxybenzothiazole ethiodide is moderately powerful in its action, and so is 1- ethylbenzothiazole ethiodide. l-phenylbenzothiazole metho-p-toluenesulfonate is also strong in its egfiect.

Salts of the naphthothiazoles are also very powerful. Among them may be noted Z-methylpenaphthothiazole meti'lo-p-toluenesulfonate, and also the methiodide and ethiodide of the same base. l-methyl-a-naphthothiazole' methiodide may also be used. I

1-phenyl-5-nitrobenzothiazole metho-p-toluene sulfonate is also powerful in its action, but it desensitizes strongly.

-Corresponding oxazole and selenazole compounds may likewise be employed, such, for in= stance, as l-methylbenzoselenazole metho ptoluene sulfonate, which is very'useful as an antifoggant.

The mercaptothiazoles are also useful for this purpose, examples being mercaptobenzthiazole, mercaptonaphthothiazole and the like, which are perfectly definite, easily available compounds.

In fact, the methods of preparation of all of the foregoing chemical compounds are described in the literature and/or in previously filed applications and resulting patents of L. G. S. Brooker, so that their preparation need not be described again here.

We are claiming as anti-foggants, therefore, those alkyl quaternary salts of the type- D/Y\OA in which Y=O, Be or S X=an acid radical A=a monovalent atom or grouping, such as hydrogen, alkyl or aryl, and

D=vinylene, ethylene, phenylene, naphthylene,

etc.

In the above formula where Y equals sulfur, for instance, the various substitutions for D would result as follows: 'vinylene would give a thiazole; ethylene, a thiazoline; phenylene, a benzothiazole; and naphthylene, a naphthothiazole alkyl quaternary salt. These are not to be confused with or even compared to the corresponding (thiazole) bases referred to in the prior art as being used for this purpose as many of them are ineffective as anti-foggants.

It will be obvious that while a small quantity of any one of the above compounds will usually give the desired anti-fogging effect, one may, if desirable, employ a mixture of a plurality of these agents. Furthermore, the anti-fogging agent may be added to the emulsion at any stage of its preparation which is convenient. It is usually added in methyl alcohol solution, although other types of solution will occur to those skilled in the art, depending upon the known solubility of the anti-fogging agent and the constitution of the emulsion to which it is added.

In addition, it has also been discovered that dyes of the thiocyanine type (such as 2,2'-dimethylthiocyanine chloride etc., see J. C. S. 1922, 121, 455; J. C. S. 1930, 2502) have an anti-fogging eflect upon photographic emulsions.

Photographic emulsions prepared as above are coated upon a suitable support to form a photographic element in a manner such as is well known to those skilled in this art.

Whatwe claim as our invention and desire to be secured by Letters Patent of the United States is:

1. A gelatino-silver-halide emulsion containing, as an antlfogging agent, a compound having the general formula:

in which 2. A gelatino-silver-halide emulsion containing, as an antifogging agent, a compound having the general formula:

-Y n \C-A a x in which =an atom selected from the group consisting of oxygen, sulfur and selenium,

A=a member selected from the group consisting of hydrogen, alkyl groups and hydrocarbon groups of the benzene series,

D=a phenylene group,

. R=an alkyl group,

X=an acid radical.

3. A gelatino-silver-hallde emulsion containing, as an antifogging agent, a compound having the general formula:

Y D/ \CA R/ x in which X=an atom selected from the group consisting of oxygen, sulfur and selenium, A=a member selected from the group consisting of hydrogen, alkyl groups and hydrocarbon groups of the benzene series, D=a naphthylene group, R=an alkyl group, X=an acid radical.

4. A gelatino-silver-halide emulsion containing,

2,131,088 as an antifogging agent, a compound having the R=an alkyl group, X:an acid radical.

5. A gelatino-silver-halide emulsion containing,

as an antifogging agent, a compound having the general formula:

Y D \CA R x in which Y=an atom selected from the group consisting of oxygen, sulfur and selenium,

A=an alkyl group,

D=a phenylene group,

R=an alkyl group,

X an acid radical.

6. A gelatino-silver-halide emulsion containing, as an antifoggant, a compound of the general formula:

in which A=an alkyl group R=an alkyl group X=an acid radical.

'7. A gelatino-silver-halide emulsion containing, as an anti-fogging agent, a compound having the general formula C-CHr in which R=an alkyl group X=an acid radical.

8. A gelatino-silver-halide emulsion containing, as an antifoggant, a compound of the general formula ca R/ x in which A=an alkyl group R=an alkyl group x=an acid radical.

9. A gelatino-silver-halide emulsion containing, as an anti-fogging agent, a compound having the general formula in which R: alkyi X=an acid radical.

10. A gelatino-silver-haiide emulsion contain- :g a l-methyl-benzothiazole methiodide as an anti-fogging agent.

11. A gelatino-silver-halide emulsion containing a l-methyl-benzothiazole etho-p-toluenesulfonate as an anti-fogging agent.

12. A process for preventing fog in gelatinosilver-halide emulsions comprising adding to the finished emulsion a compound of the following general formula:

Y D/ \CA in which Y=an atom selected from the group consisting of oxygemsulfur and selenium,

A=a member selected from the group consisting of hydrogen, alkyl groups and hydrocarbon groups of the benzene series,

D=an organic group selected from the group consisting of vinylene, ethylene, phenylene and naphthylene groups,

R=an alkyl group,

X=an acid radical.

13. A photographic silver halide emulsion containing, as an antifogging agent, a compound having the general formula:

Y D/ \CA in which Y=an atom selected from the group consisting of oxygen, sulfur and selenium,

A=a member selected from the group consisting of hydrogen, alkyl groups and hydrocarbon groups of the benzene series,

=an organic group selected from the group consisting of vinylene, ethylene, phenylene and naphthylene groups,

R=an alkyl group,

x=an acid radical.

LESLIE a. s. BROOKER. mm .1, STAUD.

US2131038A 1932-05-26 1933-05-18 Photographic emulsion containing alkyl quaternary salts of thiazoles and the like asantifoggants Expired - Lifetime US2131038A (en)

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Cited By (57)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2490745A (en) * 1948-01-13 1949-12-06 Eastman Kodak Co Cellulose carboxylic ester silver halide emulsions sensitized with benzothiazole and benzoselenazole quaternary salts
US2532744A (en) * 1945-07-04 1950-12-05 Gen Aniline & Film Corp Diazotype containing as the azo component a quaternary salt of 2-methyl-6-methoxy-benzoselenazole
US2728667A (en) * 1952-11-08 1955-12-27 Eastman Kodak Co Molecular compounds of mercury salts with benzothiazoles as fog inhibitors in a silver halide emulsion
US3062646A (en) * 1959-03-06 1962-11-06 Eastman Kodak Co Sensitization of silver halide emulsions with macrocyclic compounds
US3155517A (en) * 1962-11-08 1964-11-03 Du Pont Photographic compositions and elements
US3155515A (en) * 1961-12-08 1964-11-03 Du Pont Photographic products
US3271154A (en) * 1961-11-30 1966-09-06 Gen Aniline & Film Corp Antifogging and stabilizing agents for photography
US3278307A (en) * 1961-11-21 1966-10-11 Eastman Kodak Co Photographic process for producing prints stabilized against print-out
US3326681A (en) * 1963-08-30 1967-06-20 Polaroid Corp Photographic products and processes
US3342596A (en) * 1964-03-11 1967-09-19 Eastman Kodak Co Benzothiazolium compounds for controlling overdevelopment
US3434842A (en) * 1964-08-08 1969-03-25 Agfa Gevaert Ag Photographic silver halide emulsions stabilized with 2-imino-thiazolones
US3954478A (en) * 1973-12-21 1976-05-04 Fuji Photo Film Co., Ltd. Silver halide emulsion containing an alkenyl benzothiazolium salt as stabilizer
US4237214A (en) * 1976-12-21 1980-12-02 Fuji Photo Film Co., Ltd. Process for forming contrasty image
US4374196A (en) * 1981-02-20 1983-02-15 Eastman Kodak Company Silver halide emulsions containing latent image stabilizing compounds
US4416981A (en) * 1982-04-29 1983-11-22 E. I. Du Pont De Nemours & Co. Benzothiazoline derivatives as silver halide antifoggants
US4423140A (en) * 1982-06-25 1983-12-27 Eastman Kodak Company Silver halide emulsions containing aromatic latent image stabilizing compounds
EP0123983A2 (en) * 1983-04-13 1984-11-07 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0138543A2 (en) * 1983-10-11 1985-04-24 Fuji Photo Film Co., Ltd. Silver halide photographic light sensitive material
US4578348A (en) * 1985-03-18 1986-03-25 Eastman Kodak Company Hydrolyzed azolium speed enhancing/fog-inhibiting agents for silver halide photography
USRE32195E (en) * 1982-06-25 1986-07-01 Eastman Kodak Company Silver halide emulsions containing aromatic latent image stabilizing compounds
US4677053A (en) * 1983-04-15 1987-06-30 Yuji Mihara Silver halide photographic materials
EP0239363A2 (en) 1986-03-25 1987-09-30 Konica Corporation Light-sensitive silver halide photographic material feasible for high speed processing
US4849327A (en) * 1987-06-02 1989-07-18 Minnesota Mining And Manufacturing Company Silver halide light-sensitive material comprising benzo-bis-thiazole quaternary salts as antifogging agents
EP0369410A2 (en) * 1988-11-15 1990-05-23 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0440195A2 (en) 1990-01-31 1991-08-07 Fuji Photo Film Co., Ltd. Silver halide color photographic material
EP0562476A1 (en) 1992-03-19 1993-09-29 Fuji Photo Film Co., Ltd. A silver halide photographic emulsion and a photographic light-sensitive material
EP0563985A1 (en) 1992-04-03 1993-10-06 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5272052A (en) * 1992-08-27 1993-12-21 Eastman Kodak Company Process for the preparation of a grain stabilized high chloride tabular grain photographic emulsion (IV)
US5298387A (en) * 1992-08-27 1994-03-29 Eastman Kodak Company Process for the preparation of a grain stabilized high chloride tabular grain photographic emulsion (II)
US5389511A (en) * 1991-11-06 1995-02-14 Konica Corporation Silver halide photographic emulsion and light-sensitive silver halide photographic material making use of the same
US5411854A (en) * 1993-12-29 1995-05-02 Eastman Kodak Company Sensitivity increase from alkynylamineazole, sensitizing dye, and chalcogenazolium salt added before heat cycle
EP0691569A1 (en) 1994-07-04 1996-01-10 Kodak-Pathe Photographic emulsion with improved sensitivity
US5492805A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Blocked leuco dyes for photothermographic elements
US5492803A (en) * 1995-01-06 1996-02-20 Minnesota Mining And Manufacturing Company Hydrazide redox-dye-releasing compounds for photothermographic elements
US5492804A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Chromogenic leuco redox-dye-releasing compounds for photothermographic elements
US5620837A (en) * 1995-12-28 1997-04-15 Eastman Kodak Company Color photographic element containing benzazolium compounds
US5629144A (en) * 1994-12-23 1997-05-13 Eastman Kodak Company Epitaxially sensitized tabular grain emulsions containing speed/fog mercaptotetrazole enhancing addenda
US5631126A (en) * 1994-12-23 1997-05-20 Eastman Kodak Company Epitaxially sensitized tabular grain emulsions containing speed/fog sulfodihydroxy aryl enhancing addenda
EP0777153A1 (en) 1995-11-30 1997-06-04 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US5654134A (en) * 1994-05-18 1997-08-05 Fuji Photo Film Co., Ltd. Silver halide emulsion
US5807667A (en) * 1992-04-16 1998-09-15 Eastman Kodak Company Sensitization of selenium and iridium emulsions
US5891615A (en) * 1997-04-08 1999-04-06 Imation Corp. Chemical sensitization of photothermographic silver halide emulsions
US5928857A (en) * 1994-11-16 1999-07-27 Minnesota Mining And Manufacturing Company Photothermographic element with improved adherence between layers
US5939249A (en) * 1997-06-24 1999-08-17 Imation Corp. Photothermographic element with iridium and copper doped silver halide grains
US5958666A (en) * 1997-09-10 1999-09-28 Eastman Kodak Company Photographic element containing antifogging cycanine dyes
US6117624A (en) * 1993-06-04 2000-09-12 Eastman Kodak Company Infrared sensitized, photothermographic article
US20040033447A1 (en) * 2002-07-11 2004-02-19 Eastman Kodak Company Black-and-white aqueous photothermographic materials
EP1624337A2 (en) 2004-08-02 2006-02-08 Fuji Photo Film Co., Ltd. Silver halide holographic sensitive material and system for taking holographic images by using the same
EP1691237A2 (en) 2005-02-15 2006-08-16 Fuji Photo Film Co., Ltd. Holographic recording material and holographic recording method
US7524621B2 (en) 2007-09-21 2009-04-28 Carestream Health, Inc. Method of preparing silver carboxylate soaps
US7622247B2 (en) 2008-01-14 2009-11-24 Carestream Health, Inc. Protective overcoats for thermally developable materials
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Cited By (68)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2532744A (en) * 1945-07-04 1950-12-05 Gen Aniline & Film Corp Diazotype containing as the azo component a quaternary salt of 2-methyl-6-methoxy-benzoselenazole
US2490745A (en) * 1948-01-13 1949-12-06 Eastman Kodak Co Cellulose carboxylic ester silver halide emulsions sensitized with benzothiazole and benzoselenazole quaternary salts
US2728667A (en) * 1952-11-08 1955-12-27 Eastman Kodak Co Molecular compounds of mercury salts with benzothiazoles as fog inhibitors in a silver halide emulsion
US3062646A (en) * 1959-03-06 1962-11-06 Eastman Kodak Co Sensitization of silver halide emulsions with macrocyclic compounds
US3278307A (en) * 1961-11-21 1966-10-11 Eastman Kodak Co Photographic process for producing prints stabilized against print-out
US3271154A (en) * 1961-11-30 1966-09-06 Gen Aniline & Film Corp Antifogging and stabilizing agents for photography
US3155515A (en) * 1961-12-08 1964-11-03 Du Pont Photographic products
US3155517A (en) * 1962-11-08 1964-11-03 Du Pont Photographic compositions and elements
US3326681A (en) * 1963-08-30 1967-06-20 Polaroid Corp Photographic products and processes
US3342596A (en) * 1964-03-11 1967-09-19 Eastman Kodak Co Benzothiazolium compounds for controlling overdevelopment
US3434842A (en) * 1964-08-08 1969-03-25 Agfa Gevaert Ag Photographic silver halide emulsions stabilized with 2-imino-thiazolones
US3954478A (en) * 1973-12-21 1976-05-04 Fuji Photo Film Co., Ltd. Silver halide emulsion containing an alkenyl benzothiazolium salt as stabilizer
US4237214A (en) * 1976-12-21 1980-12-02 Fuji Photo Film Co., Ltd. Process for forming contrasty image
US4374196A (en) * 1981-02-20 1983-02-15 Eastman Kodak Company Silver halide emulsions containing latent image stabilizing compounds
US4416981A (en) * 1982-04-29 1983-11-22 E. I. Du Pont De Nemours & Co. Benzothiazoline derivatives as silver halide antifoggants
USRE32195E (en) * 1982-06-25 1986-07-01 Eastman Kodak Company Silver halide emulsions containing aromatic latent image stabilizing compounds
US4423140A (en) * 1982-06-25 1983-12-27 Eastman Kodak Company Silver halide emulsions containing aromatic latent image stabilizing compounds
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0123983A3 (en) * 1983-04-13 1988-01-13 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
US4596767A (en) * 1983-04-13 1986-06-24 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
EP0123983A2 (en) * 1983-04-13 1984-11-07 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
US4677053A (en) * 1983-04-15 1987-06-30 Yuji Mihara Silver halide photographic materials
EP0138543A2 (en) * 1983-10-11 1985-04-24 Fuji Photo Film Co., Ltd. Silver halide photographic light sensitive material
EP0138543A3 (en) * 1983-10-11 1987-12-23 Fuji Photo Film Co., Ltd. Silver halide photographic light sensitive material
US4578348A (en) * 1985-03-18 1986-03-25 Eastman Kodak Company Hydrolyzed azolium speed enhancing/fog-inhibiting agents for silver halide photography
EP0239363A2 (en) 1986-03-25 1987-09-30 Konica Corporation Light-sensitive silver halide photographic material feasible for high speed processing
US4849327A (en) * 1987-06-02 1989-07-18 Minnesota Mining And Manufacturing Company Silver halide light-sensitive material comprising benzo-bis-thiazole quaternary salts as antifogging agents
EP0369410A2 (en) * 1988-11-15 1990-05-23 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0369410A3 (en) * 1988-11-15 1990-12-05 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
US5149619A (en) * 1988-11-15 1992-09-22 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0440195A2 (en) 1990-01-31 1991-08-07 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5389511A (en) * 1991-11-06 1995-02-14 Konica Corporation Silver halide photographic emulsion and light-sensitive silver halide photographic material making use of the same
EP0562476A1 (en) 1992-03-19 1993-09-29 Fuji Photo Film Co., Ltd. A silver halide photographic emulsion and a photographic light-sensitive material
EP0563985A1 (en) 1992-04-03 1993-10-06 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5807667A (en) * 1992-04-16 1998-09-15 Eastman Kodak Company Sensitization of selenium and iridium emulsions
US5272052A (en) * 1992-08-27 1993-12-21 Eastman Kodak Company Process for the preparation of a grain stabilized high chloride tabular grain photographic emulsion (IV)
US5298387A (en) * 1992-08-27 1994-03-29 Eastman Kodak Company Process for the preparation of a grain stabilized high chloride tabular grain photographic emulsion (II)
US6117624A (en) * 1993-06-04 2000-09-12 Eastman Kodak Company Infrared sensitized, photothermographic article
US5411854A (en) * 1993-12-29 1995-05-02 Eastman Kodak Company Sensitivity increase from alkynylamineazole, sensitizing dye, and chalcogenazolium salt added before heat cycle
US5654134A (en) * 1994-05-18 1997-08-05 Fuji Photo Film Co., Ltd. Silver halide emulsion
US5696289A (en) * 1994-06-30 1997-12-09 Minnesota Mining And Manufacturing Company Blocked leuco dyes for photothermographic elements
US5492805A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Blocked leuco dyes for photothermographic elements
US5705676A (en) * 1994-06-30 1998-01-06 Minnesota Mining And Manufacturing Company Chromogenic leuco redox-dye-releasing compounds for photothermographic elements
US5492804A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Chromogenic leuco redox-dye-releasing compounds for photothermographic elements
EP0691569A1 (en) 1994-07-04 1996-01-10 Kodak-Pathe Photographic emulsion with improved sensitivity
US5928857A (en) * 1994-11-16 1999-07-27 Minnesota Mining And Manufacturing Company Photothermographic element with improved adherence between layers
US5629144A (en) * 1994-12-23 1997-05-13 Eastman Kodak Company Epitaxially sensitized tabular grain emulsions containing speed/fog mercaptotetrazole enhancing addenda
US5631126A (en) * 1994-12-23 1997-05-20 Eastman Kodak Company Epitaxially sensitized tabular grain emulsions containing speed/fog sulfodihydroxy aryl enhancing addenda
US5492803A (en) * 1995-01-06 1996-02-20 Minnesota Mining And Manufacturing Company Hydrazide redox-dye-releasing compounds for photothermographic elements
EP0777153A1 (en) 1995-11-30 1997-06-04 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US5620837A (en) * 1995-12-28 1997-04-15 Eastman Kodak Company Color photographic element containing benzazolium compounds
US5891615A (en) * 1997-04-08 1999-04-06 Imation Corp. Chemical sensitization of photothermographic silver halide emulsions
US5939249A (en) * 1997-06-24 1999-08-17 Imation Corp. Photothermographic element with iridium and copper doped silver halide grains
US6060231A (en) * 1997-06-24 2000-05-09 Eastman Kodak Company Photothermographic element with iridium and copper doped silver halide grains
US5958666A (en) * 1997-09-10 1999-09-28 Eastman Kodak Company Photographic element containing antifogging cycanine dyes
US20040033447A1 (en) * 2002-07-11 2004-02-19 Eastman Kodak Company Black-and-white aqueous photothermographic materials
US6964842B2 (en) 2002-07-11 2005-11-15 Eastman Kodak Company Black-and-white aqueous photothermographic materials
EP1624337A2 (en) 2004-08-02 2006-02-08 Fuji Photo Film Co., Ltd. Silver halide holographic sensitive material and system for taking holographic images by using the same
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