US2657135A - Photographic emulsions and solutions containing thioglycolic acid derivatives - Google Patents

Photographic emulsions and solutions containing thioglycolic acid derivatives Download PDF

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Publication number
US2657135A
US2657135A US125846A US12584649A US2657135A US 2657135 A US2657135 A US 2657135A US 125846 A US125846 A US 125846A US 12584649 A US12584649 A US 12584649A US 2657135 A US2657135 A US 2657135A
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United States
Prior art keywords
emulsion
silver halide
thioglycolylamino
compounds
acid derivatives
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US125846A
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Wesley G Lowe
Marcelle E Hamshire
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to BE494175D priority Critical patent/BE494175A/xx
Priority to US79318A priority patent/US2503861A/en
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US125846A priority patent/US2657135A/en
Priority to FR1090385D priority patent/FR1090385A/en
Priority to GB5359/50A priority patent/GB699858A/en
Application granted granted Critical
Publication of US2657135A publication Critical patent/US2657135A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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
    • C07D277/82—Nitrogen atoms
    • 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
    • G03C1/35—Antiplumming agents, i.e. antibronzing agents; Toners
    • G03C1/355—Organic derivatives of bivalent sulfur, selenium or tellurium
    • 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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29—Development processes or agents therefor
    • G03C5/305—Additives other than developers
    • 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
    • Y10S430/13—Antibronze agent or process

Definitions

  • This invention relates to photography and particularly to a method of preventing image degradation of an exposed silver halide emulsion during processing.
  • Silver halide emulsions are frequently subject to image degradation during processing, that is, during development, fixing, washing, toning, etc, and during the moist heat to which they are sub jected on drying as when prints are subjected to ferrotyping or hot-glazing. This deterioration of the image frequently manifests itself as plumming or bronzing of the image during ferrotyping. Other types of image degradation are also encountered as will become apparent hereinafter.
  • a further object is to provide a method for preventing plumming of exposed and developed photographic prints during ferrotyping.
  • a further object is to provide silver halide emulsions containing agents which reduce or prevent plumming or other types of image degradation.
  • a still further object is to provide a method for preventing or reducing various types of image deterioration during processing of an exposed silver halide layer.
  • R is any of various aryl, heterocyolic, acyl or amino groups or the acylated derivatives of these compounds.
  • the thioglycolic acid derivatives may be present in any one or more of the processing baths or may be incorporated in the sensitive emulsion layer prior to exposure or may be incorporated in an overcoating or backing layer of the sensitive material.
  • the thioglycolic derivatives are incorporated in the emulsion, they should be used in amounts of from about 2.5 to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate.
  • the same concentration of the agents should be present in the emulsion when the agents are added by bathing the emulsion in a solution con taining them.
  • the solution may contain up to about 5% of the com pound.
  • a further use of our compounds is in image protecting action, that is, stabilization of the developed image against chemical attack by such reagents as dilute cyanide or sodium thiosulfate or ammonium thiosulfate solutions such as used in fixing baths.
  • image protecting action that is, stabilization of the developed image against chemical attack by such reagents as dilute cyanide or sodium thiosulfate or ammonium thiosulfate solutions such as used in fixing baths.
  • all of the compounds listed above are suitable for this purpose.
  • a further use of our compounds is for contrast increasing, desensitizing and stabilizing action, especially where the compounds are incorporated in the sensitive emulsion layer.
  • Compounds '7, 8, 18,23, 24 and26 are especially suitable for this purpose.
  • Compound 25 is very effective for desensitizing and stabilizing action without raising contrast when the compound is incorporated in the emulsion.
  • Compound is also efi'ective in preventing hypo drag that is, erratic tone changes in the print when placed into hypo without adequate washing after development.
  • a still further use of our compounds is in cold toning, that is, in producing blue-black tones upon processing the emulsion layer. ilompcunds 16, 19, 20, 21, 22
  • the method of preventing image degradation of an exposed silver halide emulsion during processing which comprises developing, fixing, washin and drying said emulsion, and performing at least one of the steps of developing, fixing,
  • washing and drying said emulsion in the presence in said emulsion of from 2.5 grams to 25 grams per unit of silver halide'formed from 1000 grams of silver nitrate, of a compound selected from those compounds having the formula an appreciable amount but less than 5%, of a compound having the general formula amqncocmsn where R'is an aryl group, and processing said exposed emulsion in said bath.
  • the method of preventing image degradation of an exposedsilver halide emulsion during processing which comprises developing, fixing, Washing and drying said emulsion, and incorporating in at least one of the developing, fixing and washing baths used to' process said emulsion, an appreciable amount but less than 5%, of a compound having the general formula where R is a heterocyclic group, and processing said exposed emulsion in said bath.
  • the method of preventing image degradation of an exposed silver halide emulsion durin processing which comprises developing, fixing, washing and drying said emulsion, and incorporating in at least one of the developing, fixing and washing baths used to process said emulsion, an appreciable amount but less than 5%, of a com pound having the general formula where R is an acyl radical, and processing said exposed emulsion in said bath.
  • a photographic silver halide emulsion containing frdm 2.5' to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate, of a compound selected from those compounds having the formula where R is selected from the class consisting of aryl, heterocyclic and acyl groups, and the acetylated derivatives of said compounds.
  • a photographic silver halide emulsion containing from 2.5 to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate, of a thioglycolylamino heterocyclic compound.
  • a photographic silver halide emulsion containing from 2.5 to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate, of a compound selected from the group consisting of 4,6 dichloro 5 methyl 2 m thioglycolylaminobenzoylaminophenol, 2 hydroxy- 3,5 dichloro 4- methylthioglycolic anilide, 2- hydroxy 5 chlorothioglyeolic anilide, 2,4,6- trichloro 5 thioglycolylamino phenol, p e thicglycolylamino w cyanoacetophenone, thioglycolic anilide, 2 thioglycolylamino 4 methyl phenol, 2 thioglycolylamino 5 methyl phenol, 2 hydroxy 4 thioglycolylamino diphenyl, 2 thioglycolylamino phenol, 2' (p thicglycolylamin
  • dichloroanilide 5-thioglycolylamino-l-naphthol, 2 (thioglycolylamino)benzothiazole, 5 'thioglycolylaminotetrazole, 2 thioglycolylaminopyrimidine, 5 thioglycolylamino 1,2,4 triazole, thioglycolylurea, thioglycolic-w-aminocapramid and thioglycolic-2,6-dihydroxy anilide.

Description

Patented Oct. 27, 1953 PHOTOGRAPHIC EMULSION S AND SOLU- TIONS CONTAINING THIOGLYCOLIC ACID DERIVATIVES Wesley G. Lowe and Marcelle E. Hamshire, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application November 5, 1949, Serial No. 125,846
7 Claims. 1
This invention relates to photography and particularly to a method of preventing image degradation of an exposed silver halide emulsion during processing.
Silver halide emulsions are frequently subject to image degradation during processing, that is, during development, fixing, washing, toning, etc, and during the moist heat to which they are sub jected on drying as when prints are subjected to ferrotyping or hot-glazing. This deterioration of the image frequently manifests itself as plumming or bronzing of the image during ferrotyping. Other types of image degradation are also encountered as will become apparent hereinafter.
It is accordingly an object of our invention to provide a method for preventing image degradation of an exposed silver halide emulsion during processing. A further object is to provide a method for preventing plumming of exposed and developed photographic prints during ferrotyping. A further object is to provide silver halide emulsions containing agents which reduce or prevent plumming or other types of image degradation. A still further object is to provide a method for preventing or reducing various types of image deterioration during processing of an exposed silver halide layer. Other objects will appear from the following description of our invention.
These objects are accomplished by performing one or more of the steps of developing, fixing, washing and drying an exposed silver halide emulsion in the presence of a thioglycolic acid amide derivative of the following formula:
where R is any of various aryl, heterocyolic, acyl or amino groups or the acylated derivatives of these compounds. The thioglycolic acid derivatives may be present in any one or more of the processing baths or may be incorporated in the sensitive emulsion layer prior to exposure or may be incorporated in an overcoating or backing layer of the sensitive material.
The following thioglycollic acid derivatives exemplify those which may beused according to our invention.
1. 4,6 dichloro methyl-Z-m-thioglycolylamino benzoylaminophenol 2. 2 hydroxy-3,5-dichloro 4 methylthioglycolic anilide 3. 2 hydroxy 5 chlorothioglycolic anilide 4. 2,4,6-trichloro-5-thioglycolylamino phenol 5. p thioglycolylamino w.- cyanoacetophenone 6. Thioglycolic anilide 7. 2 thioglycolylamino- 4 methyl phenol 2 9. 2 hydroxy 4 thioglycolylamino diphenyl 1 10. 2 thioglycolylamino phenol 11. 2 (p thioglycolylaminophenylacetamino) 4,6 dichloro 5 methyl phenol NHzNHCOCHzSI-I 26. Thioglycolic 2,6 dihydroxy anilide When incorporated in silver halide emulsions. these compounds are preferably used in a gelatino silver chloride emulsion or a silver chloride emulsion containing small amounts of bromide or iodide. Silver halide emulsions in which the carrier is-polyvinyl alcohol or hydrolyzed cellulose acetate may also be used. When. the thioglycolic derivatives are incorporated in the emulsion, they should be used in amounts of from about 2.5 to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate. The same concentration of the agents should be present in the emulsion when the agents are added by bathing the emulsion in a solution con taining them. When the emulsion layer is bathed in a solution of the compound, the solution may contain up to about 5% of the com pound.
Not all of the compounds used according to our invention are equally effective for preventing or reducing all types of image degradation, although the listed compounds have been found to have some value in most cases. For preventing plumming, that is, loss of reflection density or tone change on hot ferrotyping of photographic prints, all of the specific compounds listed above are effective. The acylated derivatives of these compounds are less effective in general, although the following acylated compounds have been found to be very satisfactory in antiplumming action.
4,6 dichloro 5 methyl 2 m acetyl thioglycolylaminobenzoylaminophenol,
5-acetylthioglycolylamino 1-naphthol,
2- (acetyl thioglycolylamino) benzothlazole.
A further use of our compounds is in image protecting action, that is, stabilization of the developed image against chemical attack by such reagents as dilute cyanide or sodium thiosulfate or ammonium thiosulfate solutions such as used in fixing baths. In general, all of the compounds listed above are suitable for this purpose.
A further use of our compounds is for contrast increasing, desensitizing and stabilizing action, especially where the compounds are incorporated in the sensitive emulsion layer. Compounds '7, 8, 18,23, 24 and26 are especially suitable for this purpose.
Compound 25 is very effective for desensitizing and stabilizing action without raising contrast when the compound is incorporated in the emulsion.
Compound is also efi'ective in preventing hypo drag that is, erratic tone changes in the print when placed into hypo without adequate washing after development. A still further use of our compounds is in cold toning, that is, in producing blue-black tones upon processing the emulsion layer. ilompcunds 16, 19, 20, 21, 22
and 23 are especially suitable for this purpose as are the following acetylated compounds:
7 2- acetylthioglycolylamido benzothiazole 5acetylthioglycolylaminotetrazole 2-acetylthioglycolylaminopyrimidine Acetothioglycolyl-4-cyanoamide We are aware that thioglycolic anilides have been used in photographic emulsions as described,
for example, in Weissberger, Kibler and Young U. S. Patent 2,448,939. In that case, however, the compound were used for color-forming purposes and were added to the emulsion in much larger amounts than are used according to the present invention. No image degradation prevention was sought or obtained inv the Weiss berger, Kibler-and Young process with the large.
amount of thioglycolic compound used. Since the silver is usually removed in a color process, silver is not present after processing and during ferrotyping so that no image protecting action would be required or obtained.
We claim 1. The method of preventing image degradation of an exposed silver halide emulsion during processing, which comprises developing, fixing, washin and drying said emulsion, and performing at least one of the steps of developing, fixing,
washing and drying said emulsion in the presence in said emulsion of from 2.5 grams to 25 grams per unit of silver halide'formed from 1000 grams of silver nitrate, of a compound selected from those compounds having the formula an appreciable amount but less than 5%, of a compound having the general formula amqncocmsn where R'is an aryl group, and processing said exposed emulsion in said bath.
3. The method of preventing image degradation of an exposedsilver halide emulsion during processing, Which comprises developing, fixing, Washing and drying said emulsion, and incorporating in at least one of the developing, fixing and washing baths used to' process said emulsion, an appreciable amount but less than 5%, of a compound having the general formula where R is a heterocyclic group, and processing said exposed emulsion in said bath.
- 4. The method of preventing image degradation of an exposed silver halide emulsion durin processing, which comprises developing, fixing, washing and drying said emulsion, and incorporating in at least one of the developing, fixing and washing baths used to process said emulsion, an appreciable amount but less than 5%, of a com pound having the general formula where R is an acyl radical, and processing said exposed emulsion in said bath.
5. A photographic silver halide emulsion containing frdm 2.5' to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate, of a compound selected from those compounds having the formula where R is selected from the class consisting of aryl, heterocyclic and acyl groups, and the acetylated derivatives of said compounds.
r 6. A photographic silver halide emulsion containing from 2.5 to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate, of a thioglycolylamino heterocyclic compound.
'7. A photographic silver halide emulsion containing from 2.5 to 25 grams per unit of silver halide formed from 1000 grams of silver nitrate, of a compound selected from the group consisting of 4,6 dichloro 5 methyl 2 m thioglycolylaminobenzoylaminophenol, 2 hydroxy- 3,5 dichloro 4- methylthioglycolic anilide, 2- hydroxy 5 chlorothioglyeolic anilide, 2,4,6- trichloro 5 thioglycolylamino phenol, p e thicglycolylamino w cyanoacetophenone, thioglycolic anilide, 2 thioglycolylamino 4 methyl phenol, 2 thioglycolylamino 5 methyl phenol, 2 hydroxy 4 thioglycolylamino diphenyl, 2 thioglycolylamino phenol, 2' (p thicglycolylaminophenyl-acetamino)' 4,6 dichloro- 5 methyl phenol, 4 nitrothioglycolyl anilide, 2,4 dichlorothioglycolyl anilide, thioglycolyl-4- iodo anilide, thioglycolio 4 sulfamido anilide,
thioglycolic 4 cyanoanilide, thioglycolic 2,5-
dichloroanilide, 5-thioglycolylamino-l-naphthol, 2 (thioglycolylamino)benzothiazole, 5 'thioglycolylaminotetrazole, 2 thioglycolylaminopyrimidine, 5 thioglycolylamino 1,2,4 triazole, thioglycolylurea, thioglycolic-w-aminocapramid and thioglycolic-2,6-dihydroxy anilide.
WESLEY G. LOWE. MARCELLE E. HAMSHIRE;
References Cited in the file of this patent 1' Great Britain o es, 1949

Claims (1)

1. THE METHOD OF PREVENTING IMAGE DEGRADATION OF AN EXPOSED SILVER HALIDE EMULSION DURING PROCESSING, WHICH COMPRISES DEVELOPING, FIXING, WASHING AN DRYING SAID EMULSION, AND PERFORMING AT LEAST ONE OF THE STEPS OF DEVELOPING, FIXING, WASHING AND DRYING SAID EMULSION IN THE PRESENCE IN SAID EMULSION OF FROM 2.5 GRAMS TO 25 GRAMS PER UNIT OF SILVER HALIDE FORMED FROM 1000 GRAMS OF SILVER NITRATE, OF A COMPOUND SELECTED FROM THE THOSE COMPOUNDS HAVING THE FORMULA
US125846A 1949-03-02 1949-11-05 Photographic emulsions and solutions containing thioglycolic acid derivatives Expired - Lifetime US2657135A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE494175D BE494175A (en) 1949-03-02
US79318A US2503861A (en) 1949-03-02 1949-03-02 2-(mercaptoacetamido)-benzothiazole and its s-acetyl derivative
US125846A US2657135A (en) 1949-03-02 1949-11-05 Photographic emulsions and solutions containing thioglycolic acid derivatives
FR1090385D FR1090385A (en) 1949-03-02 1950-03-01 Improvements in photography and products for their realization
GB5359/50A GB699858A (en) 1949-03-02 1950-03-02 Improvements in the production of photographic images

Applications Claiming Priority (2)

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US79318A US2503861A (en) 1949-03-02 1949-03-02 2-(mercaptoacetamido)-benzothiazole and its s-acetyl derivative
US125846A US2657135A (en) 1949-03-02 1949-11-05 Photographic emulsions and solutions containing thioglycolic acid derivatives

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US125846A Expired - Lifetime US2657135A (en) 1949-03-02 1949-11-05 Photographic emulsions and solutions containing thioglycolic acid derivatives

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2721800A (en) * 1953-08-12 1955-10-25 Eastman Kodak Co Photographic elements containing antifogging agents
US2852380A (en) * 1955-06-21 1958-09-16 Eastman Kodak Co Photographic emulsions and solutions containing silver salts of thioglycolic derivatives

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2694717A (en) * 1954-11-16 Cxnhc o o chchac o oh
NL72814C (en) * 1949-02-01
BE519582A (en) * 1952-04-30
BE612311A (en) * 1962-01-05
US3326684A (en) * 1962-04-06 1967-06-20 Fuji Photo Film Co Ltd Method for stabilizing developed photosensitive materials

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1673522A (en) * 1925-07-25 1928-06-12 Ig Farbenindustrie Ag Process of manufacturing photographic silver halide emulsions and products obtained thereby
US1758576A (en) * 1928-01-31 1930-05-13 Agfa Ansco Corp Light-sensitive silver-halide emulsions and process of manufacturing the same
US2448939A (en) * 1944-06-10 1948-09-07 Eastman Kodak Co Thioglycolic amide couplers
US2453346A (en) * 1945-10-25 1948-11-09 Eastman Kodak Co Stabilization of processed photographic emulsions to high temperatures and humidities
GB631184A (en) * 1946-10-01 1949-10-28 Eastman Kodak Co Improvements in the processing of photographic materials

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1673522A (en) * 1925-07-25 1928-06-12 Ig Farbenindustrie Ag Process of manufacturing photographic silver halide emulsions and products obtained thereby
US1758576A (en) * 1928-01-31 1930-05-13 Agfa Ansco Corp Light-sensitive silver-halide emulsions and process of manufacturing the same
US2448939A (en) * 1944-06-10 1948-09-07 Eastman Kodak Co Thioglycolic amide couplers
US2453346A (en) * 1945-10-25 1948-11-09 Eastman Kodak Co Stabilization of processed photographic emulsions to high temperatures and humidities
GB631184A (en) * 1946-10-01 1949-10-28 Eastman Kodak Co Improvements in the processing of photographic materials

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2721800A (en) * 1953-08-12 1955-10-25 Eastman Kodak Co Photographic elements containing antifogging agents
US2852380A (en) * 1955-06-21 1958-09-16 Eastman Kodak Co Photographic emulsions and solutions containing silver salts of thioglycolic derivatives

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US2503861A (en) 1950-04-11
FR1090385A (en) 1955-03-30
GB699858A (en) 1953-11-18

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