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Silver halide emulsions containing alkyl esters of benzimidazole carbamic acid antifogging agents

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US3499761A
US3499761A US3499761DA US3499761A US 3499761 A US3499761 A US 3499761A US 3499761D A US3499761D A US 3499761DA US 3499761 A US3499761 A US 3499761A
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silver
emulsion
light
halide
sensitive
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Fritz Dersch
Sally L Paniccia
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GAF Chemicals Corp
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/30Nitrogen atoms not forming part of a nitro radical
    • C07D235/32Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
    • 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

United States Patent 3,499,761 SILVER HALIDE EMULSIONS CONTAINING AL- KYL ESTERS 0F BENZIMIDAZOLE CARBAMIC ACID ANTIFOGGING AGENTS Fritz Dersch, Binghamton, and Sally L. Paniccia, Endwell, N.Y., assignors to GAF Corporation, New York, N.Y., a corporation of Delaware No Drawing. Filed July 20, 1964, Ser. No. 383,963 Int. Cl. G03c 1/34, 5/30 US. Cl. 96--66.5 17 Claims ABSTRACT OF THE DISCLOSURE A light sensitive photographic material comprising a silver halide emulsion and an anti-foggant compound contained therein, or in a layer contiguous therewith; the anti-foggant being an alkyl ester of benzimidazole carbamic acid.

The present invention relates, in general, to photographic materials comprising light-sensitive silver halide emulsions and, in particular, to stabilized silver halide emulsions which have less tendency to fog without substantial reduction in the light sensitivity thereof.

It is well established that light sensitive emulsions such as gelatin-silver halide emulsions are subject to fogging. Fogging in general and chemical fogging in particular may be defined as a uniform deposit of silver extending over and either partially or wholly obliterating the image and is caused in a number of ways; namely the nature of the emulsion, its age and the conditions under which it has been stored, the nature of the developer, impurities in the developing solution, and the time and temperature of the development. Additionally, chemical fogging is also promoted when such active agents as metol are employed in a concentrated solution or are used in the presence of an excess of alkali. Similarly, the oxidation of certain developing agents such as metol and hydroquinone exerts a powerful fogging action.

While a great number of antifoggants and stabilizers have been heretofore suggested as effective in preventing an increase in fogging and as a result thereof stabilize or control the keeping qualities of light sensitive silver halide emulsions, many of these compounds lower the sensitivity of silver halide emulsions and reduce the optical or dye sensitizing ability of the emulsions.

Accordingly, it is a primary object of this invention to provide stabilizers or fog inhibiting agents which tend to prevent the formation of chemical fog in light-sensitive silver halide emulsions.

A further object is to provide stabilizers or antifogging agents for light-sensitive silver halide emulsions which do not appreciably lower the sensitivity of the silver halide emulsions.

Yet another object is to provide a stabilizer or antifoggant which, when added to photographic gelatin or to photographic emulsion, will prevent speed loss of the emulsion during its storage.

A still further object is to provide stabilizers or antifogging agents for light-sensitive silver halide emulsions which do not reduce the sensitivity to light of longer wave length affected by the presence of sensitizing dyes.

Still further objects and advantages will become further apparent from the following detailed description thereof.

It has been discovered that the above objects are readily accomplished by intimately associating with silver halide emulsions certain alkyl esters of benzimidazole carbamic acids of the following formula:

Y NH

wherein X is hydrogen, a halo radical such as chloro, fiuoro, bromo or iodo radicals and alkyl or alkoxy radicals containing less than seven carbon atoms in the alkyl group, n is a whole positive integer of less than four, R represents hydrogen, potassium, sodium, ammonium or lower aliphatic hydrocarbon radicals such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, or amyl; and Y represents hydrogen, chloro, nitro, methyl or ethyl radicals.

While the above general formula is indicative of the class of benzimidazole carbamic acids operable to produce the antifogging effects observed, it is generally believed that such effects are attributable to the presence in the silver halide emulsions of the benzimidazole structure and not necessarily dependent upon the length or particular configuration of the substituents X, Y and R although their presence in the nucleus cannot entirely be discounted.

Typical and representative compounds within the scope of the general formula set forth above include:

' benzimidazole-Z-car-bamic acid, isoamyl ester benzimidazole-Z-carbarnic acid, hexyl ester 5-methyl-6-nitrobenzimidazole-Z-carbamie acid, hexyl ester 4,6-dichlorobenzimidazole-2-carbamic acid, propyl ester 5-fiuorobenzimidazole-Z-carbamic acid, methyl ester 4-nitrobenzimidazole-2-carbamic acid, ethyl ester 4,7-dichloro-S-methylbenzimidazole-Z-carbamic acid amyl ester 1 5,7-dimethyl-4-chlorobenzimidazole-Z-carbamic acid,

isopropyl ester S-methoxybenzimidazole-2-carbamic acid, methyl ester 4,5,6,7-tetrachlorobenzimidazole-2-carbamic acid, butyl ester 5,6-dichloro-4-isopropoxybenzimidazole-Z-carbamic acid;

methyl ester S-bromo-6-butylbenzimidazole-Z-carbamic acid, ethyl ester 4,5,6,7-tetramethylbenzimidazole-Z-carbamic acid,

isobutyl ester Beneficial effects in fog reduction are obtained when solutions of the antifoggant are incorporated into the silver halide emulsions as ripening finals or as coating finals. Ripening finals are added during the ripening or the sensitivity increasing stage of the emulsion making process, whereas .coating finals are added to the silver halide emulsion just prior to the coating of the emulsion on a suitable support, such as, for example, paper, glass or film.

The addition of the antifoggants can be made before,

during or after the addition of the soluble silver salt to the soluble halide in the presence of a suitable carrier or colloid such as gelatin, polyvinyl alcohol, solubilized casein, albumin, and the like.

If desired, the antifoggants of the present invention can also be employed as components of the developing solution.

The amount of antifogging agent employed as additives to the light sensitive emulsions varies from about 0.1 to about 50 milligrams of antifoggant per 0.6 mole of silver halide. When the antifogging agents are employed as ripening finals it has been found advantageous to employ them in amounts in the range of from about 0.1 to about 25 milligrams per 0.6 mole of silver halide, whereas when the antifogging agents are employed in coating finals, it has been found advantageous to employ amounts in the range of from about 0.5 to about 50 milligrams of antifoggant per 0.6 mole of silver halide. Obviously, the development of optimum characteristics within the ranges set forth above will depend, in part, upon the type of emulsion employed and can be readily determined in each case.

In some cases, it has been found advantageous to apply the antifogging agents of the invention to adjacent layers, for example, in a separate undercoating layer or in the antiabrasion gelatin surface. Alternatively, it has been found advantageous, in some cases, to apply the antifogging agents of the invention in one or all processing baths or in pre and post baths.

It has also been found that the antifogging agents of the invention can be compatibly employed in combination with other known antifoggants and stabilizers; with sulfur, reductionand metal-, and noble metal sensitizers as well as in combination with polyoxyalkylene polyols, their derivatives; polyvinylpyrrolidones and other accelerators.

The following examples will serve to illustrate the practice of the invention:

EXAMPLE I A silver halide emulsion in gelatin containing 2% silver iodide and 98% silver bromide Was prepared in a conventional manner and brought up to its maximum light sensitivity. It was then readied for coating, finals were added, such as sensitizing dyes and hardening agents. A 0.1% solution of benzimidazole-2-carbamic acid, ethyl ester was added to the emulsion as an antifoggant and stabilizer.

The so-prepared emulsion samples were coated on a suitable cellulose ester base and dried. Samples of these film coatings were then exposed in a Type IB Sensitometer and developed in a developer of the following composition:

A silver halide emulsion in gelatin containing 2% silver iodide and 98% silver bromide was coated on film base in a manner known to the art. After the coating, a solution containing 20 grams of gelatin in 1 liter of H and a 0.1% solution of benzimidaz le-z-ca bamic acid.

ethyl ester was coated thereon as an anti-abrasion layer. After drying, film samples were exposed and processed as described in Example I. The samples exhibited no speed loss in oven storage tests with a fog reduction of 0.02 compared to a speed loss from to 88 with the stabilizers presently in use.

EXAMPLE III An emulsion was prepared and coated in the manner described in Example I, but development was carried out at a temperature of F. In this case, the type, which did not include an antifoggant, developed to a fog of 0.48, Whereas when 1 mg. of ethyl ester was used per kilo of emulsion the sample developed to a fog of only 0.28, with less speed loss than the type.

The antifogging agents which have been found to provide beneficial effects when incorporated into light sensitive silver halide emulsions can be readily prepared by known procedures such as described in US. 3,010,968, issued Nov. 28, 1961.

Various modifications of the invention will occur to persons skilled in the art. Thus, it is evident in lieu of the compounds of the specific examples, any of the compounds mentioned above can be employed with similar results. Therefore, it is not intended that the invention be limited in the patent granted except as necessitated by the appended claims.

What is claimed is:

1. A light sensitive photographic material comprising a light sensitive silver halide emulsion, a carrier therefor and an antifoggant characterized by the general formula:

Y NH

wherein X represents a member of the group consisting of hydrogen, chloro, fluoro, bromo, iodo and alkyl and alkoxy radicals containing less than seven carbon atoms, n is a whole positive integer of less than four, R represents a member selected from the group consisting of hydrogen, potassium, sodium, ammonium and aliphatic hydrocarbon radicals containing from one to six carbon atoms, and Y represents a member selected from the group consisting of hydrogen, chloro, nitro, methyl, ethyl and propyl.

2. The material as defined in claim 1 wherein the antifoggant is located in the silver halide emulsion.

3. The material as defined in claim 1 wherein the antifoggant is located in a layer adjacent the silver halide emulsion.

4. A light sensitive photographic material comprising a light sensitive silver halide emulsion and a carrier therefor, said emulsion containing, as an antifoggant, benzimidazole-Z-carbamic acid, ethyl ester.

5. A light sensitive photographic material comprising a light sensitive ilver halide emulsion and a carrier therefor, said emulsion containing, as an antifoggant, S-methyl- 6-nitrobenzimadazole-Z-carbamic acid, hexyl ester.

6. A light sensitive photographic material comprising a light sensitive silver halide emulsion and a carrier therefor, said emulsion containing, as an antifoggant, 4,6-dichlorobenzimidazole-Z-carbamic acid, propyl ester.

7. A light sensitive photographic material comprising a light sensitive silver halide emulsion and a carrier therefor, said emulsion containing, as an antifoggant, S-fluorobenzimidazole-2-carbamic acid, methyl ester.

8. A light sensitive photographic material comprising a light sensitive silver halide emulsion and a carrier there for, said emulsion containing, a an antifoggant, 4-nitrobenzimidazole-Z-carbamic acid, ethyl ester.

9. A light sensitive photographic material comprising a light sensitive silver halide emulsion and a carrier therefor, said emulsion containing, as an antifoggant, 4,7- dichloro-5-methylbenzimidazole 2 carbamic acid, amyl ester.

10. A light sensitive photographic material comprising a light sensitive silver halide emulsion and a carrier therefor, said emulsion containing as an antifoggant, 5,7-dimethyl-4-chlorobenzimidazole-Z-carbamic acid, isopropyl ester.

11. A light sensitive photographic material comprising a light sensitive silver halide emulsion and a carrier therefor, said emulsion containing, as an antifoggant, S-methoxybenzimidazole-Z-carbamic acid, methyl ester.

12. A light sensitive photographic material comprising a light sensitive silver halide emulsion and a carrier therefor, said emulsion containing, as an antifoggant, 4,5,6,7- tetrachlorobenzimidazole-Z-carbamic acid, butyl ester.

13. A light sensitive photographic material comprising a light sensitive silver halide emulsion and a carrier therefor, said emulsion containing, as an antifoggant, 5,6-dichloro 4 isopropoxybenzimidazole 2 carbamic acid, methyl ester.

14. A light sensitive photographic material comprising a light sensitive silver halide emulsion and a carrier therefor, said emulsion containing, as an antifoggant, 5-bromo- 6-butylbenzimidazole-Z-carbamic acid, ethyl ester.

15. A light sensitive photographic material comprising a light sensitive silver halide emulsion and a carrier therefor, said emulsion containing, as an antifoggant, 4,5, 6,7- tetramethylbenzimidazole-Z-carbamic acid, isobutyl ester.

16. A process of minimizing and preventing fog in light sensitive silver halide materials comprising a base having a light sensitive silver halide emulsion thereon, which comprises exposing said emulsion to light and developing the same in the presence of an antifoggant characterized by the formula:

wherein X represents a member of the group consisting of hydrogen, chloro, fluoro, bromo, iodo, :alkyl and alkoxy radicals containing less than seven carbon atoms in the alkyl group, n is a Whole positive integer of less than four, R represents a member selected from the group consisting of hydrogen, potassium, sodium, ammonium and aliphatic hydrocarbon radicals and Y represents a member selected from the group consisting of hydrogen, chloro, nitro, methyl, ethyl and propyl.

References Cited UNITED STATES PATENTS 3,023,103 2/1962 'Dersch et a1 96-109 3,137,578 6/1964 de Selms 96-109 3,255,202 6/1966 Johnson 96-109 3,271,154 9/1966 Dersch et al. 96-109 NORMAN G. TORCHIN, Primary Examiner R. E. FIGHTER, Assistant Examiner US. Cl. X.R. 96-109

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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3655391A (en) * 1969-05-16 1972-04-11 Paoli Merli Azodicarbonamide fog inhibitors
US3982947A (en) * 1974-03-14 1976-09-28 Agfa-Gevaert, N.V. Fog-inhibitors for silver halide photography silver halide photographic material containing an iodo benzene compound as antifoggant
US4131467A (en) * 1977-11-23 1978-12-26 E. I. Du Pont De Nemours And Company 4,7-Dihydroxybenzimidazole hydrobromide as antifogger
US4572892A (en) * 1984-05-21 1986-02-25 Eastman Kodak Company Direct positive photographic elements with incorporated maximum density enhancing antifoggants
US6245789B1 (en) 1998-05-19 2001-06-12 The Procter & Gamble Company HIV and viral treatment
US6265427B1 (en) 1995-06-07 2001-07-24 The Proctor & Gamble Company Pharmaceutical composition for the method of treating leukemia
US6271217B1 (en) 1997-01-28 2001-08-07 The Procter & Gamble Company Method of treating cancer with a benzimidazole and a chemotherapeutic agent
WO2001083457A2 (en) * 2000-04-28 2001-11-08 The Procter & Gamble Company Benzimidazole-2-carbamates and their use in cancer treatment
US6362207B1 (en) 1995-04-12 2002-03-26 The Procter & Gamble Company Methods of treating viral infections with benzimidazoles
US6380232B1 (en) 2000-09-26 2002-04-30 The Procter & Gamble Company Benzimidazole urea derivatives, and pharmaceutical compositions and unit dosages thereof
US6407105B1 (en) 2000-09-26 2002-06-18 The Procter & Gamble Company Compounds and methods for use thereof in the treatment of cancer or viral infections
US6407131B1 (en) 1997-05-16 2002-06-18 The Procter & Gamble Company Compounds and method for use thereof in the treatment of cancer or viral infections
US6423734B1 (en) 1999-08-13 2002-07-23 The Procter & Gamble Company Method of preventing cancer
US6462062B1 (en) 2000-09-26 2002-10-08 The Procter & Gamble Company Compounds and methods for use thereof in the treatment of cancer or viral infections
US6479526B1 (en) 1995-04-12 2002-11-12 The Procter & Gamble Company Pharmaceutical composition for inhibiting the growth of viruses and cancers
US6608096B1 (en) 2000-09-26 2003-08-19 University Of Arizona Foundation Compounds and methods for use thereof in the treatment of cancer or viral infections

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3023103A (en) * 1960-08-02 1962-02-27 Gen Aniline & Film Corp Antifoggants and stabilizers for photographic silver halide emulsions
US3137578A (en) * 1962-02-07 1964-06-16 Eastman Kodak Co Photographic emulsions containing 2-heterocyclic benzimidazole antifoggants
US3255202A (en) * 1963-08-23 1966-06-07 Union Carbide Corp Process for the preparation of 2-(acylamidoalkyl)benzimidazoles
US3271154A (en) * 1961-11-30 1966-09-06 Gen Aniline & Film Corp Antifogging and stabilizing agents for photography

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3023103A (en) * 1960-08-02 1962-02-27 Gen Aniline & Film Corp Antifoggants and stabilizers for photographic silver halide emulsions
US3271154A (en) * 1961-11-30 1966-09-06 Gen Aniline & Film Corp Antifogging and stabilizing agents for photography
US3137578A (en) * 1962-02-07 1964-06-16 Eastman Kodak Co Photographic emulsions containing 2-heterocyclic benzimidazole antifoggants
US3255202A (en) * 1963-08-23 1966-06-07 Union Carbide Corp Process for the preparation of 2-(acylamidoalkyl)benzimidazoles

Cited By (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3655391A (en) * 1969-05-16 1972-04-11 Paoli Merli Azodicarbonamide fog inhibitors
US3982947A (en) * 1974-03-14 1976-09-28 Agfa-Gevaert, N.V. Fog-inhibitors for silver halide photography silver halide photographic material containing an iodo benzene compound as antifoggant
US4131467A (en) * 1977-11-23 1978-12-26 E. I. Du Pont De Nemours And Company 4,7-Dihydroxybenzimidazole hydrobromide as antifogger
US4572892A (en) * 1984-05-21 1986-02-25 Eastman Kodak Company Direct positive photographic elements with incorporated maximum density enhancing antifoggants
US6362207B1 (en) 1995-04-12 2002-03-26 The Procter & Gamble Company Methods of treating viral infections with benzimidazoles
US6653335B2 (en) 1995-04-12 2003-11-25 University Of Arizona Foundationa Pharmaceutical composition for inhibiting the growth of viruses and cancers
US6479526B1 (en) 1995-04-12 2002-11-12 The Procter & Gamble Company Pharmaceutical composition for inhibiting the growth of viruses and cancers
US6552059B2 (en) 1995-06-07 2003-04-22 University Of Arizona Foundation Pharmaceutical composition for and method of treating leukemia
US6265427B1 (en) 1995-06-07 2001-07-24 The Proctor & Gamble Company Pharmaceutical composition for the method of treating leukemia
US6329355B1 (en) 1997-01-28 2001-12-11 The Procter & Gamble Company Method for inhibiting the growth of cancers
US6271217B1 (en) 1997-01-28 2001-08-07 The Procter & Gamble Company Method of treating cancer with a benzimidazole and a chemotherapeutic agent
US6900235B1 (en) 1997-05-16 2005-05-31 Uaf Technologies And Research, Llc Benzimidazole compounds, and pharmaceutical compositions and unit dosages thereof
US20050119236A1 (en) * 1997-05-16 2005-06-02 University Of Arizona Foundation Cancer treatments and pharmaceutical compositions therefor
US6407131B1 (en) 1997-05-16 2002-06-18 The Procter & Gamble Company Compounds and method for use thereof in the treatment of cancer or viral infections
US6420411B1 (en) 1997-05-16 2002-07-16 The Procter & Gamble Company Compounds and methods for use thereof in the treatment of cancer or viral infections
US20050192328A1 (en) * 1997-05-16 2005-09-01 Uaf Technologies And Research, Llc Compounds and methods for use thereof in the treatment of viral infections
US6423736B1 (en) 1997-05-16 2002-07-23 The Proctor & Gamble Company Compounds and methods for use thereof in the treatment of cancer or viral infections
US6423735B1 (en) 1997-05-16 2002-07-23 The Procter & Gamble Company Compounds and methods for use thereof in the treatment of cancer or viral infections
US6864275B1 (en) 1997-05-16 2005-03-08 Uaf Technologies And Research, Llc Compounds and methods for use thereof in the treatment of cancer
US20050288349A1 (en) * 1997-05-16 2005-12-29 Uaf Technologies And Research, Llc Cancer treatments and pharmaceutical compositions therefor
US6482843B1 (en) 1997-05-16 2002-11-19 The Procter & Gamble Company Compounds and methods for use thereof in the treatment of cancer or viral infections
US6506783B1 (en) 1997-05-16 2003-01-14 The Procter & Gamble Company Cancer treatments and pharmaceutical compositions therefor
US6710065B1 (en) 1997-05-16 2004-03-23 Uaf Technologies And Research, Llc Compounds and methods for use thereof in the treatment of cancer
US6984654B2 (en) 1997-05-16 2006-01-10 Uaf Technologies And Research, Llc Cancer treatments and pharmaceutical compositions therefor
US6245789B1 (en) 1998-05-19 2001-06-12 The Procter & Gamble Company HIV and viral treatment
US6423734B1 (en) 1999-08-13 2002-07-23 The Procter & Gamble Company Method of preventing cancer
US6906091B2 (en) 1999-08-13 2005-06-14 Uaf Technologies And Research, Llc Method of cancer treatment
WO2001083457A3 (en) * 2000-04-28 2002-03-21 Procter & Gamble Benzimidazole-2-carbamates and their use in cancer treatment
WO2001083457A2 (en) * 2000-04-28 2001-11-08 The Procter & Gamble Company Benzimidazole-2-carbamates and their use in cancer treatment
US6407105B1 (en) 2000-09-26 2002-06-18 The Procter & Gamble Company Compounds and methods for use thereof in the treatment of cancer or viral infections
US6462062B1 (en) 2000-09-26 2002-10-08 The Procter & Gamble Company Compounds and methods for use thereof in the treatment of cancer or viral infections
US6720349B2 (en) 2000-09-26 2004-04-13 Uaf Technologies And Research, Llc Compounds for use in the treatment of cancer or viral infections
US20030100592A1 (en) * 2000-09-26 2003-05-29 University Of Arizona Foundation Compounds and methods for use thereof in the treatment of viral infections
US6916836B2 (en) 2000-09-26 2005-07-12 Uaf Technologies And Research, Llc Compounds and methods for use thereof in the treatment of viral infections
US6930121B2 (en) 2000-09-26 2005-08-16 Uaf Technologies And Research, Llc Compounds and methods for use thereof in the treatment of viral infections
US6380232B1 (en) 2000-09-26 2002-04-30 The Procter & Gamble Company Benzimidazole urea derivatives, and pharmaceutical compositions and unit dosages thereof
US20040029942A1 (en) * 2000-09-26 2004-02-12 University Of Arizona Foundation Compounds and methods for use thereof in the treatment of viral infections
US6608096B1 (en) 2000-09-26 2003-08-19 University Of Arizona Foundation Compounds and methods for use thereof in the treatment of cancer or viral infections

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