US2728668A - Photographic emulsions containing a 1,2-dithiolane - Google Patents

Photographic emulsions containing a 1,2-dithiolane Download PDF

Info

Publication number
US2728668A
US2728668A US324390A US32439052A US2728668A US 2728668 A US2728668 A US 2728668A US 324390 A US324390 A US 324390A US 32439052 A US32439052 A US 32439052A US 2728668 A US2728668 A US 2728668A
Authority
US
United States
Prior art keywords
silver halide
dithiolane
emulsion
emulsions
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US324390A
Inventor
Mochel Walter Edwin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to US324390A priority Critical patent/US2728668A/en
Application granted granted Critical
Publication of US2728668A publication Critical patent/US2728668A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/09—Noble metals or mercury; Salts or compounds thereof; Sulfur, selenium or tellurium, or compounds thereof, e.g. for chemical sensitising
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/15—Lithographic emulsion
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/167—X-ray

Definitions

  • This invention pertains to photography and more particularly to photographic silver halide emulsions of enhanced sensitivity, and to their preparation.
  • An object of this invention is to provide new means for improving the sensitivity of photographic silver halide emulsions. Another object is to provide colloid silver halide emulsions of enhanced speed. A further object is to provide such emulsions wherein the added adjuvant does not have an adverse efiect on the spectral properties of the emulsion. Still other objects will be apparent from the following description of the invention.
  • photographic emulsions of silver halide in synthetic water-permeable colloid binding agents which emulsions contain an organic compound containing a 1,2-dithiolane nucleus and more particularly a [1,2-dithiolane-3-yl]alkanoic acid and its alkali metal, ammonium, substituted ammonium and amine salts have a marked increase in their light-sensitiveness.
  • Suitable salts include the sodium, potassium, tetramethylammonium, dimethylamine, diethylamine, trimethylamine, triethylamine, and cyclohexylamine salts.
  • the colloid silver halide emulsions contain a small amount of 5[1,2-dithiolane-3-yllpentanoic acid.
  • This acid has the formula:
  • the 1,2- dithiolane compound can be incorporated in the silver halide emulsion at various stages in its preparation and in various manners.
  • it can be added to the fluid silver halide emulsion in crystalline form or from water or a water-miscible solvent, e. g., methanol or ethanol.
  • a water-miscible solvent e. g., methanol or ethanol.
  • It can be added in similar manner to the solutions used in making the silver halide emulsion, for example, in the colloid solution.
  • it can be added to the emulsion at the silver halide precipitation stage or at any later stage prior to coating onto a support, e. g., film or paper as a light-sensitive layer. It preferably is added after the initial preparation of the silver halide 2,728,668 Patented Dec. 27,
  • the 1,2-dithiolane compound confers to the final colloid silver halide emulsion a sensitiveness of the optical type and gives it an overall increase in speed, as distinguished from the extra range of spectral sensitivity conferred by sensitizing dyes.
  • the compound can be used with such dyes, thereby modifying the normal sensitivity and speed of emulsions.
  • Example I mide and adjusting the pAg to a value of 8.33.
  • To 150 parts of the silver bromide dispersion is added 50 parts of 2.5% solution of the polyvinyl alcohol made by the complete hydrolysis of polyvinyl acetate as described in U. S. Patent 2,579,016, and 0.1 part of 5[l,2-dithiolane- 3-yllpentanoic acid in 2 parts of ethanol.
  • a 20 cc. sample of this solution is exposed to light and the exposed silver halide developed with 5 cc.
  • the 1,2'dithiolane compound can be used in various amounts, a practical range being from 1 to 250 milligrams and a preferred range being from 5 to 50 milligrams of said compound per mol of silver halide. However, as indicated by the example, up to 40% by weight of the compound, based on the silver halide can be used.
  • the invention obviously is not limited to the preparation of colloid silver bromide emulsions as simple and mixed silver halide emulsions of various kinds, e. g., silver chloride, silver chloride bromide, silver bromide iodide, silver chloride iodide, etc., develop a marked increase in speed, without any deleterious elfect, by the addition of the 1,2-dithiolane compound.
  • colloids for silver halide grains
  • collodion polyglycuronic acid, polyvinyl acetals containing a large num ber of intralinear recurring CH2 and CHOH groups
  • polyvinyl acetaldehyde acetal polyvinyl butyraldehyde acetal
  • polyvinyl o-sulfobenzaldehyde acetal the polyvinyl acetal color formers described in U. S.
  • Suitable additional 1,2-dithiolane compounds which can be incorporated in the colloid silver halide in like manner and equivalent amount include 1,2-dithiolane, 4-acetyl- 1,2-din1io1ane, and the esters and amides of [l,2-dithi I As stated above, the compounds can be used withcon- V nine, hemicyanine and styryl dyes and with the usual:
  • Silver halide emulsions made in accordance with the invention' may be used to prepare photographic films and papers for many and various purposes including multicolor films, X-ray film, lithographic film, portrait film,
  • the invention has the advantage that it provides the art with new means for increasing the speed of photographic silver halide emulsions. Another advantage is that increases in speed can be attained without any new or tedious emulsion techniques. A further advantage is that the increase in speed is not attended by any deleterious disadvantages.
  • An emulsion of light-sensitive silver halide in a synthetic, water-permeable colloid said emulsion containing a 1,2-dithiolane compound.
  • An emulsion of light-sensitive silver halide in a synthetic, water-permeable colloid said emulsion contain- --ing from l -to 250 milligrams of a [1,2-dithiolane-3- yl]alkanoic acid per mole of silver halide.
  • An emulsion of light sensitive silver halide in a synthetic, water-permeable colloid said emulsion containing from 1 to 250 milligrams of 5[1,2-dithiolane-3- yllpentanoic acid per mole of silver halide.
  • An emulsion of light-sensitive silver halide in a synthetic, water-permeable colloid said emulsion contain- 6.
  • An emulsion of light-sensitive silver halide in a synthetic water-permeable colloid said emulsion containing from 1 to 250 milligrams of compound taken from the group consisting of [1,2-dithiolane-3-yl]alkanoic acid and its alkali metal, ammonium, substituted ammonium,
  • An emulsion of light-sensitive silver halide in a synthetic, water-permeable colloid said emulsion containing from 1 to 250 milligrams, of a compound taken from the group consisting of 5[1,2-dithiolane-3-yllpentanoic acid and its alkali metal, ammonium, substituted ammonium and amine salts, per mole of silver halide.

Description

United States Patenf r PHOTOGRAPHIC EMULSIONS CONTAINING A 1,2-DITHIOLANE Walter Edwin Mochel, Bellefonte, Del., assignor to E. I. du Pont de Nemours and Company, Wilmington, Del.,
a corporation of Delaware No Drawing. Application December 5, 1952,
. Serial No. 324,390
7 Claims. (Cl. 95-7) This invention pertains to photography and more particularly to photographic silver halide emulsions of enhanced sensitivity, and to their preparation.
Various sulfur compounds have been added to photographic silver halide emulsions to improve them for diverse purposes. Thus, allyl isothiocyanate, allyl thiocarbimide, allyl diethyl thiourea, phenyl isothiocyanate, sodium thiosulfate, etc., have been added to emulsions to increase their light-sensitiveness. Other compounds including di-o-formylalkylaminodiphenyl disulfides have been added to emulsions as anti-fogging agents. Still other cyclic organic sulfur-containing compounds including the l-hydrocarbon S-mercaptotetrazoles have been added to photographic paper silver halide emulsions as. antiplumming or anti-fogging agents. t
An object of this invention is to provide new means for improving the sensitivity of photographic silver halide emulsions. Another object is to provide colloid silver halide emulsions of enhanced speed. A further object is to provide such emulsions wherein the added adjuvant does not have an adverse efiect on the spectral properties of the emulsion. Still other objects will be apparent from the following description of the invention.
It has been found that photographic emulsions of silver halide in synthetic water-permeable colloid binding agents, which emulsions contain an organic compound containing a 1,2-dithiolane nucleus and more particularly a [1,2-dithiolane-3-yl]alkanoic acid and its alkali metal, ammonium, substituted ammonium and amine salts have a marked increase in their light-sensitiveness. Suitable salts include the sodium, potassium, tetramethylammonium, dimethylamine, diethylamine, trimethylamine, triethylamine, and cyclohexylamine salts.
In the preferred aspect of the invention the colloid silver halide emulsions contain a small amount of 5[1,2-dithiolane-3-yllpentanoic acid. This acid has the formula:
and has been named oc-lipOic acid. A method of preparing it has been described in Jour. Am. Chem. Soc., vol. 74, pp. 1868-9 and 3455 (1952). The salts of the above acid can be made by neutralization of the acid with the appropriate base.
The 1,2- dithiolane compound can be incorporated in the silver halide emulsion at various stages in its preparation and in various manners. Thus, it can be added to the fluid silver halide emulsion in crystalline form or from water or a water-miscible solvent, e. g., methanol or ethanol. It can be added in similar manner to the solutions used in making the silver halide emulsion, for example, in the colloid solution. Thus, it can be added to the emulsion at the silver halide precipitation stage or at any later stage prior to coating onto a support, e. g., film or paper as a light-sensitive layer. It preferably is added after the initial preparation of the silver halide 2,728,668 Patented Dec. 27,
emulsion but before the final digestion stage has been concluded.
The 1,2-dithiolane compound confers to the final colloid silver halide emulsion a sensitiveness of the optical type and gives it an overall increase in speed, as distinguished from the extra range of spectral sensitivity conferred by sensitizing dyes. The compound can be used with such dyes, thereby modifying the normal sensitivity and speed of emulsions. 1
The invention will be further illustrated but is not intended to be limited by the following example.
Example I mide and adjusting the pAg to a value of 8.33. To 150 parts of the silver bromide dispersion is added 50 parts of 2.5% solution of the polyvinyl alcohol made by the complete hydrolysis of polyvinyl acetate as described in U. S. Patent 2,579,016, and 0.1 part of 5[l,2-dithiolane- 3-yllpentanoic acid in 2 parts of ethanol. When a 20 cc. sample of this solution is exposed to light and the exposed silver halide developed with 5 cc. of a 0.1 M solution of p-methylaminophenol bulfered with sodium hydrogen phosphate to a pH 7, and excess silver bromide removed by treatment with a fixing solution of sodium thiosulfate, a black deposit of silver remains. When compared with a similar control emulsion free from said 5[1,2-dithiolane-3-yl]pentanoic acid exposed, developed and fixed in like manner the sensitiveness of the first emulsion is 5 to 7 times greater, as indicated by optical density measurements, than that of the latter control emulsion.
The 1,2'dithiolane compound can be used in various amounts, a practical range being from 1 to 250 milligrams and a preferred range being from 5 to 50 milligrams of said compound per mol of silver halide. However, as indicated by the example, up to 40% by weight of the compound, based on the silver halide can be used.
While in the foregoing example the compound was added after precipitation of the halide and there were no digestion, washing, second digestion or ripening steps to bring the emulsion to its maximum sensitivity, these conventional procedures obviously would be used in commercial practice. After adding the 1,2-dithiolane to the emulsion it is desirable to heat the emulsion before coating at temperatures from 60 F. to F. for one-half to four hours.
The invention obviously is not limited to the preparation of colloid silver bromide emulsions as simple and mixed silver halide emulsions of various kinds, e. g., silver chloride, silver chloride bromide, silver bromide iodide, silver chloride iodide, etc., develop a marked increase in speed, without any deleterious elfect, by the addition of the 1,2-dithiolane compound.
Various other synthetic water-permeable colloid binding agents for silver halide grains can be used in place of the specific one described in the foregoing example. Among the additional useful colloids are collodion, polyglycuronic acid, polyvinyl acetals containing a large num ber of intralinear recurring CH2 and CHOH groups including polyvinyl acetaldehyde acetal, polyvinyl butyraldehyde acetal, polyvinyl o-sulfobenzaldehyde acetal the polyvinyl acetal color formers described in U. S. Patents 2,310,943, 2,320,422, 2,380,032, 2,380,033, 2,397,864, etc., the methacrylamide/acrylic acid, etc. copolymers described in U- S. Patents 2,311,548, 2,592,107, 2,611,763, etc.
Suitable additional 1,2-dithiolane compounds which can be incorporated in the colloid silver halide in like manner and equivalent amount include 1,2-dithiolane, 4-acetyl- 1,2-din1io1ane, and the esters and amides of [l,2-dithi I As stated above, the compounds can be used withcon- V nine, hemicyanine and styryl dyes and with the usual:
color formers, etc.
. Silver halide emulsions made in accordance with the invention'may be used to prepare photographic films and papers for many and various purposes including multicolor films, X-ray film, lithographic film, portrait film,
etc.
The invention has the advantage that it provides the art with new means for increasing the speed of photographic silver halide emulsions. Another advantage is that increases in speed can be attained without any new or tedious emulsion techniques. A further advantage is that the increase in speed is not attended by any deleterious disadvantages.
As many widely ditferent embodiments of this invention can be made without departing from the spirit and scope thereof, it is to be understood that the invention is not to be limited except as defined by the claims.
What is claimed is:
v1. An emulsion of light-sensitive silver halide in a synthetic, water-permeable colloid, said emulsion containing a 1,2-dithiolane compound.
2. An emulsion of light-sensitive silver halide in a synthetic, water-permeable colloid, said emulsion contain- --ing from l -to 250 milligrams of a [1,2-dithiolane-3- yl]alkanoic acid per mole of silver halide.
4. An emulsion of light sensitive silver halide in a synthetic, water-permeable colloid, said emulsion containing from 1 to 250 milligrams of 5[1,2-dithiolane-3- yllpentanoic acid per mole of silver halide.
5. A polyvinyl alcohol light-sensitive silver halide emulsion containing from 1 to 250 milligrams of 5[1,2-dithiolane-3-yl1pentanoic acid per mole of silver halide.
ing a 1,2-dithiolane compound containing a carboxylic group.
3. An emulsion of light-sensitive silver halide in a synthetic, water-permeable colloid, said emulsion contain- 6. An emulsion of light-sensitive silver halide in a synthetic water-permeable colloid, said emulsion containing from 1 to 250 milligrams of compound taken from the group consisting of [1,2-dithiolane-3-yl]alkanoic acid and its alkali metal, ammonium, substituted ammonium,
and amine salts, per mole of silver halide.
7. An emulsion of light-sensitive silver halide in a synthetic, water-permeable colloid, said emulsion containing from 1 to 250 milligrams, of a compound taken from the group consisting of 5[1,2-dithiolane-3-yllpentanoic acid and its alkali metal, ammonium, substituted ammonium and amine salts, per mole of silver halide.
References Cited in the file of this patent UNITED STATES PATENTS OTHER REFERENCES The Ring Index by Patterson and Capell.
Pub. by Reinhold Pub. Corp. (1940), page 43.

Claims (1)

1. AN EMULSION OF LIGHT-SENSITIVE HALIDE IN A SYNTHETIC, WATER-PERMEABLE COLLOID, SAID EMULSION CONTAINING A 1,2-DITHIOLANE COMPOUND.
US324390A 1952-12-05 1952-12-05 Photographic emulsions containing a 1,2-dithiolane Expired - Lifetime US2728668A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US324390A US2728668A (en) 1952-12-05 1952-12-05 Photographic emulsions containing a 1,2-dithiolane

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US324390A US2728668A (en) 1952-12-05 1952-12-05 Photographic emulsions containing a 1,2-dithiolane

Publications (1)

Publication Number Publication Date
US2728668A true US2728668A (en) 1955-12-27

Family

ID=23263370

Family Applications (1)

Application Number Title Priority Date Filing Date
US324390A Expired - Lifetime US2728668A (en) 1952-12-05 1952-12-05 Photographic emulsions containing a 1,2-dithiolane

Country Status (1)

Country Link
US (1) US2728668A (en)

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2948614A (en) * 1957-07-11 1960-08-09 Stabilized photographic silver halede
US3049549A (en) * 1954-03-22 1962-08-14 Research Corp Lipoic acid and derivatives
US3128186A (en) * 1960-07-15 1964-04-07 Gen Foods Corp Stabilized photographic silver halide emulsions
US3622329A (en) * 1968-04-26 1971-11-23 Agfa Gevaert Ag Photographic silver halide emulsions with increased sensitivity
US3859100A (en) * 1972-03-29 1975-01-07 Fuji Photo Film Co Ltd Silver halide photographic material containing a hydroxyazaidene and a carboxyl substituted 1,2-dithiolane as stabilizing combination
EP0106306A2 (en) 1982-10-14 1984-04-25 Fuji Photo Film Co., Ltd. Silver halide color photographic materials
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
EP0115351A2 (en) 1983-01-28 1984-08-08 Fuji Photo Film Co., Ltd. Silver halide light-sensitive material
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
EP0200206A2 (en) 1985-04-30 1986-11-05 Konica Corporation Silver halide photographic light-sensitive material
EP0201027A2 (en) 1985-04-30 1986-11-12 Konica Corporation Silver halide photographic light-sensitive material
EP0202784A2 (en) 1985-04-23 1986-11-26 Konica Corporation Silver halide photographic light-sensitive material
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
EP0228084A2 (en) 1985-12-25 1987-07-08 Fuji Photo Film Co., Ltd. Image forming process
EP0239363A2 (en) 1986-03-25 1987-09-30 Konica Corporation Light-sensitive silver halide photographic material feasible for high speed processing
EP0476327A1 (en) 1990-08-20 1992-03-25 Fuji Photo Film Co., Ltd. Data-retainable photographic film product and process for producing color print
EP0514675A1 (en) 1991-04-22 1992-11-25 Fuji Photo Film Co., Ltd. Silver halide photographic materials and method for processing the same
EP0563708A1 (en) 1992-03-19 1993-10-06 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion and light-sensitive material using the same
EP0566079A2 (en) * 1992-04-16 1993-10-20 Eastman Kodak Company Aqueous, solid particle dispersions of dichalcogenides for photographic emulsions and coatings
EP0566080A2 (en) * 1992-04-16 1993-10-20 Eastman Kodak Company Silver halide photographic emulsions sensitized in the presence of organic dichalcogenides
EP0566074A2 (en) * 1992-04-16 1993-10-20 Eastman Kodak Company Silver halide photographic emulsions precipitated in the presence of organic dichalcogenides
EP0580041A2 (en) 1992-07-10 1994-01-26 Fuji Photo Film Co., Ltd. Method of processing silver halide photographic material and composition for processing
EP0589460A1 (en) 1992-09-24 1994-03-30 Fuji Photo Film Co., Ltd. Method for processing a black & white silver halide light-sensitive material
US5318887A (en) * 1991-06-06 1994-06-07 Konica Corporation Method for production of silver halide emulsion, and silver halide photographic light-sensitive 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
EP0693710A1 (en) 1994-07-18 1996-01-24 Konica Corporation Silver halide photographic element and processing method thereof
US20060121397A1 (en) * 2003-01-31 2006-06-08 Konica Minolata Photo Imaging Inc. Silver halide emulsion silver halide photographic sensitive material and method of image formation
EP1750173A1 (en) 2005-08-04 2007-02-07 Fuji Photo Film Co., Ltd. Silver halide photosensitive material and packaged body containing the same

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1678832A (en) * 1927-06-06 1928-07-31 Eastman Kodak Co Photographic light-sensitive material and process of making the same
US1742042A (en) * 1927-01-07 1929-12-31 Agfa Ansco Corp Sensitized element, silver halid emulsion therefor, and process of manufacturing thesame
GB664230A (en) * 1948-11-18 1952-01-02 Kodak Ltd Improvements in sensitive photographic emulsions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1742042A (en) * 1927-01-07 1929-12-31 Agfa Ansco Corp Sensitized element, silver halid emulsion therefor, and process of manufacturing thesame
US1678832A (en) * 1927-06-06 1928-07-31 Eastman Kodak Co Photographic light-sensitive material and process of making the same
GB664230A (en) * 1948-11-18 1952-01-02 Kodak Ltd Improvements in sensitive photographic emulsions

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3049549A (en) * 1954-03-22 1962-08-14 Research Corp Lipoic acid and derivatives
US2948614A (en) * 1957-07-11 1960-08-09 Stabilized photographic silver halede
US3128186A (en) * 1960-07-15 1964-04-07 Gen Foods Corp Stabilized photographic silver halide emulsions
US3622329A (en) * 1968-04-26 1971-11-23 Agfa Gevaert Ag Photographic silver halide emulsions with increased sensitivity
US3859100A (en) * 1972-03-29 1975-01-07 Fuji Photo Film Co Ltd Silver halide photographic material containing a hydroxyazaidene and a carboxyl substituted 1,2-dithiolane as stabilizing combination
EP0106306A2 (en) 1982-10-14 1984-04-25 Fuji Photo Film Co., Ltd. Silver halide color photographic materials
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
EP0115351A2 (en) 1983-01-28 1984-08-08 Fuji Photo Film Co., Ltd. Silver halide light-sensitive material
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
EP0202784A2 (en) 1985-04-23 1986-11-26 Konica Corporation Silver halide photographic light-sensitive material
EP0200206A2 (en) 1985-04-30 1986-11-05 Konica Corporation Silver halide photographic light-sensitive material
EP0201027A2 (en) 1985-04-30 1986-11-12 Konica Corporation Silver halide photographic light-sensitive material
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
EP0228084A2 (en) 1985-12-25 1987-07-08 Fuji Photo Film Co., Ltd. Image forming process
EP0239363A2 (en) 1986-03-25 1987-09-30 Konica Corporation Light-sensitive silver halide photographic material feasible for high speed processing
EP0476327A1 (en) 1990-08-20 1992-03-25 Fuji Photo Film Co., Ltd. Data-retainable photographic film product and process for producing color print
EP0514675A1 (en) 1991-04-22 1992-11-25 Fuji Photo Film Co., Ltd. Silver halide photographic materials and method for processing the same
US5318887A (en) * 1991-06-06 1994-06-07 Konica Corporation Method for production of silver halide emulsion, and silver halide photographic light-sensitive 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
EP0563708A1 (en) 1992-03-19 1993-10-06 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion and light-sensitive material using the same
EP0566074A2 (en) * 1992-04-16 1993-10-20 Eastman Kodak Company Silver halide photographic emulsions precipitated in the presence of organic dichalcogenides
EP0566080A2 (en) * 1992-04-16 1993-10-20 Eastman Kodak Company Silver halide photographic emulsions sensitized in the presence of organic dichalcogenides
EP0566079A3 (en) * 1992-04-16 1995-01-04 Eastman Kodak Co Aqueous, solid particle dispersions of dichalcogenides for photographic emulsions and coatings.
EP0566080A3 (en) * 1992-04-16 1995-01-04 Eastman Kodak Co Silver halide photographic emulsions sensitized in the presence of organic dichalcogenides.
EP0566074A3 (en) * 1992-04-16 1995-01-04 Eastman Kodak Co Silver halide photographic emulsions precipitated in the presence of organic dichalcogenides.
EP0566079A2 (en) * 1992-04-16 1993-10-20 Eastman Kodak Company Aqueous, solid particle dispersions of dichalcogenides for photographic emulsions and coatings
EP0580041A2 (en) 1992-07-10 1994-01-26 Fuji Photo Film Co., Ltd. Method of processing silver halide photographic material and composition for processing
EP0589460A1 (en) 1992-09-24 1994-03-30 Fuji Photo Film Co., Ltd. Method for processing a black & white silver halide light-sensitive material
EP0693710A1 (en) 1994-07-18 1996-01-24 Konica Corporation Silver halide photographic element and processing method thereof
US20060121397A1 (en) * 2003-01-31 2006-06-08 Konica Minolata Photo Imaging Inc. Silver halide emulsion silver halide photographic sensitive material and method of image formation
US7220537B2 (en) 2003-01-31 2007-05-22 Konica Minolta Photo Imaging, Inc. Silver halide emulsion silver halide photographic sensitive material and method of image formation
EP1750173A1 (en) 2005-08-04 2007-02-07 Fuji Photo Film Co., Ltd. Silver halide photosensitive material and packaged body containing the same

Similar Documents

Publication Publication Date Title
US2728668A (en) Photographic emulsions containing a 1,2-dithiolane
US2403927A (en) Improvers for photographic emulsions
US3033682A (en) Radiation-sensitive emulsions, elements, and processes for making same
US3241971A (en) Photographic silver halide emulsions
US3294540A (en) Lith-type emulsions with block co-polymers
US3479186A (en) Emulsion binders
US2521926A (en) Chemical sensitization of photographic emulsions
US4067740A (en) Trithiocarbonates as sensitizers for silver halide emulsions
US3573920A (en) Fine grain silver halide emulsions containing novel dye combinations
US2756148A (en) Photographic emulsion having clayden effect susceptibility
US3728126A (en) Silver halide emulsion containing an organic selenium compound antifogging agent
US3369905A (en) Photographic silver halide emulsions containing polyamine sensitizing agents
US3420667A (en) Substituted quinones and dimine quinones as silver halide sensitizers
US2293261A (en) Photographic material
US3178293A (en) Radiation-sensitive elements and their preparation
US3006762A (en) Sensitizers for photographic emulsions
US2743183A (en) Chemical sensitization of photographic emulsions
US2833650A (en) Photographic emulsions
US2444609A (en) Stabilizers for photographic silverhalide emulsions
US3663230A (en) Light-sensitive silver halide photographic emulsions
US2398778A (en) Sensitized photographic emulsion
US3449126A (en) Fog stabilized photographic emulsion
US3576637A (en) Lith-type of emulsion containing pyrozolone
US1758576A (en) Light-sensitive silver-halide emulsions and process of manufacturing the same
US2472627A (en) Fog inhibitor for photographic emulsions