US2948615A - Antifoggants and stabilizers for photographic silver halide emulsions - Google Patents

Antifoggants and stabilizers for photographic silver halide emulsions Download PDF

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Publication number
US2948615A
US2948615A US721100A US72110058A US2948615A US 2948615 A US2948615 A US 2948615A US 721100 A US721100 A US 721100A US 72110058 A US72110058 A US 72110058A US 2948615 A US2948615 A US 2948615A
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United States
Prior art keywords
silver halide
emulsion
antifoggants
stabilizers
antifoggant
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Expired - Lifetime
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US721100A
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English (en)
Inventor
Dersch Fritz
Angelus Millet R De
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GAF Chemicals Corp
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General Aniline and Film Corp
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Priority to BE576406D priority Critical patent/BE576406A/xx
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US721100A priority patent/US2948615A/en
Priority to GB7915/59A priority patent/GB858326A/en
Priority to DEG26610A priority patent/DE1106169B/de
Application granted granted Critical
Publication of US2948615A publication Critical patent/US2948615A/en
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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/48—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides
    • H01M4/56—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of lead
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B26—HAND CUTTING TOOLS; CUTTING; SEVERING
    • B26F—PERFORATING; PUNCHING; CUTTING-OUT; STAMPING-OUT; SEVERING BY MEANS OTHER THAN CUTTING
    • B26F1/00—Perforating; Punching; Cutting-out; Stamping-out; Apparatus therefor
    • B26F1/02—Perforating by punching, e.g. with relatively-reciprocating punch and bed
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B42—BOOKBINDING; ALBUMS; FILES; SPECIAL PRINTED MATTER
    • B42B—PERMANENTLY ATTACHING TOGETHER SHEETS, QUIRES OR SIGNATURES OR PERMANENTLY ATTACHING OBJECTS THERETO
    • B42B5/00—Permanently attaching together sheets, quires or signatures otherwise than by stitching
    • B42B5/08—Permanently attaching together sheets, quires or signatures otherwise than by stitching by finger, claw or ring-like elements passing through the sheets, quires or signatures
    • B42B5/10—Permanently attaching together sheets, quires or signatures otherwise than by stitching by finger, claw or ring-like elements passing through the sheets, quires or signatures the elements being of castellated or comb-like form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/14—Electrodes for lead-acid accumulators
    • H01M4/16—Processes of manufacture
    • H01M4/22—Forming of electrodes
    • H01M4/23—Drying or preserving electrodes after forming
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T74/00—Machine element or mechanism
    • Y10T74/18—Mechanical movements
    • Y10T74/18888—Reciprocating to or from oscillating
    • Y10T74/1892—Lever and slide
    • Y10T74/1896—Cam connections
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T83/00—Cutting
    • Y10T83/869—Means to drive or to guide tool
    • Y10T83/8821—With simple rectilinear reciprocating motion only
    • Y10T83/8828—Plural tools with same drive means
    • Y10T83/8831—Plural distinct cutting edges on same support
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T83/00—Cutting
    • Y10T83/869—Means to drive or to guide tool
    • Y10T83/8821—With simple rectilinear reciprocating motion only
    • Y10T83/8841—Tool driver movable relative to tool support
    • Y10T83/8845—Toggle links, one link pivoted to tool support

Definitions

  • the present invention relates to the use of antifogging and stabilizing agents for photographic silver halide emulsions and, more particularly, to the use for such purposes of carboxyalkyl-ethyl-pyridyl or -quinolyl thioethers in whlch the ethyl thioether group is in the 2- or 4-position of the pyridine or quinoline ring, and the salts and esters of said thioethers.
  • v I It is known that light-sensitive emulsions such as photographic silver halide emulsions have a tendency to fog. This fog may be caused in a number of ways, as, for example, by excessive ripening of the emulsion, during storage of the film or paper particularly at elevated temperatures and humidity, or by prolonged development of the exposed emulsion.
  • carboxyalkyl-ethyl-Z or 4- pyridyl or -quinolyl thioethers, their salts and esters are not only excellent stabilizers or antifogging agents for silver halide emulsions but, in addition, they have the happy faculty of performing this function without lowering the sensitivity of the emulsion with which they are associated or without reducing the sensitivity of the emulsion to light of longer wave length attributable to the presence of sensitizing dyes.
  • n is a whole number of from 1 to 3; and R is hydrogen, alkyl, such as methyl, .ethyLpropyl, butyl, amyl and the like; hydroxyalkyl, i.e., hydroxymethyl, hydroxyethyl and the like; carboxyalkyl, i.e., carboxymethyl, carboxyethyl and the like; aryl such 2 as phenyl, tolyl, naphthyl, carboxyphenyl, sulfophenyl and the like; aralkyl such as benzyl or a cation such as hydrogen, sodium, potassium, silver, ammonium or the like.
  • alkyl such as methyl, .ethyLpropyl, butyl, amyl and the like
  • hydroxyalkyl i.e., hydroxymethyl, hydroxyethyl and the like
  • carboxyalkyl i.e., carboxymethyl, carboxyethyl and the
  • butyl and benzyl esters (8) a-4 -quinolyl-ethyl thio acetic acid and its sodium and potassium salts (9) fi-(a-2-quinolyl-ethyl thio) propionic acid (10) [i-(a-4-quinolyl-ethyl thio) propionic acid (11) -(a-2-pyridyl-ethyl thio) butyric acid (12) -(a-4-quinolyl-ethyl thio) butyric acid
  • the above compounds may be prepared by the method described in U.S.P. 2,810,724 whileselecting the desired vinyl pyridine or vinyl quinoline and the desired mercapto lower aliphatic acid. In general, this method envisages the addition of a mol equivalent of the mercapto lower aliphatic acid to the selected vinyl pyridine or 01' as coating finals.
  • quinoline in the presence of a polymerization inhibitor such as, for instance, an anti-oxidant like hydroquinone.
  • a polymerization inhibitor such as, for instance, an anti-oxidant like hydroquinone.
  • the reaction mixture may be heated to low temperatures such as 4060 C. to complete the reaction.
  • the reaction product is treated with ether or ethanol and collected by filtration.
  • the solid product may be purified with charcoal and recrystallized from ethanol.
  • the free acid produced by this method may be converted to its salt by reacting the same with a water soluble salt containing the desired cation such as potassium carbonate, sodium carbonate, ammonium carbonate, silver nitrate or the like.
  • a water soluble salt containing the desired cation such as potassium carbonate, sodium carbonate, ammonium carbonate, silver nitrate or the like.
  • esters of the free acids are prepared in the conventional manner by refluxing the same with the selected alcohol or phenol in the presence of hydrochloric acid.
  • Coating finals are added to the emulsion just prior to coating on a suitablesupport such as glass, paper or film at a time when the emulsion has nearly obtained its maximum sensitivity.
  • our antifoggants or stabilizers are best employed in a concentration of 1 to milligrams per .6 mol of silver halide and when used as coating finals in a concentration of 10 to 300 milligrams per .6 mol of silver halide.
  • concentration depends very much on the type of emulsion which is used, and it is advisable to determine the optimum concentration from case to case.
  • antifoggants and stabilizers may be employed in connection with any type of photographic emulsion, e.g., non-sensitized, orthochromatic, panchromatic, X-ray emulsions, paper emulsions, color emulsions or the like. They may be used in combination with other known antifoggants and stabilizers, reductionand metaland noble metal sensitizers or in combination with hydroxypolyethenoxy derivatives, i.e., those obtained by reacting ethylene oxide with an alcohol, phenol, amine or the like. (See U.S.P. 1,970,578.)
  • 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 1% solution of a-4-pyridyl-ethyl thio acetic acid was added to the emulsion as an antifoggant and stabilizer. The emulsion samples contained about .6 mol of silver halide. 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 IIB Sensitometer and developed in a developer of the following composition:
  • the antifoggant has the following formula:
  • Example 11 The procedure was the same as in Example I excepting that the a-4 pyridyl-ethyl thio acetic acid was replaced by an equivalent quantity of a-2-pyridyl-ethyl thio acetic acid. The results were similar-to those obtained in Example I.
  • the antifoggant of this example was prepared in the same way as that of Example I excepting that 2-vinyl pyridine was used in lieu of 4-vinyl pyridine.
  • the antifoggant has the following formula:
  • Example III The procedure was the same as in Example I excepting that there was used an equivalent quantity of p-(a-4- pyridyl-ethyl thio) propionic acid.
  • Example IV The procedure was the same as in Example I excepting that there was used as the antifoggant 'y-(a-4pyridylethyl thio) butyric acid. The results paralleled those of Example I.
  • the antifoggant was prepared by the method of U.S.P. 2,810,724 but while using -mercapto butyric acid in place of B-mercapto propionic acid.
  • Example V The procedure was the same as in Example I excepting that there was used as the antifoggant fi-(a-4-quinolylethyl thio) propionic acid.
  • This antifoggant was prepared by the method of U.S.P. 2,810,724 but while using 4-vinyl quinoline in place of 4-vinyl pyridine.
  • Example VI An exposed sample of a photographic film was developed for 12 minutes at 65 C. in a standard metolhydroquinone developer. Another exposed sample was similarly developed in the same developing solution except that milligrams of the compound of Example! per liter of developer were added. Sensitometn'c strips developed in the standard developer (control) showed a fog of .30 whereas those strips which were developed in the developer containing the antifoggant had a fog of .20.
  • Example VII The procedure was the same as in Example VI excepting that there was used as the antifoggant 'y-(a-2- quinolyl-ethyl thio) butyric acid. The results were similar to those obtained in Example VI.
  • A' light-sensitive photographic material comprising a base and a light-sensitive silver halide emulsion layer, said light-sensitive material containing as an antifoggant a compound selected from the class consisting of those of the following formulae:
  • n is a Whole number of from 1 to 3;
  • R is selected from the class consisting of alkyl, aryl, ar'alkyl and a. cation, and the sulfur-containing substituent group on the designated nitrogenous heterocyclic ring is in a position selected from the class consisting of the 2- and 4- position of such ring.
  • n is a whole number of from 1 to 3; R is selected from the class consisting of alkyl, aryl, aralkyl and a cation, and the sulfur-containing substituent group on the designated nitrogenous heterocyclic ring is in a position selected from the class consisting of the 2 and 4- position of such ring.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Electrochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Forests & Forestry (AREA)
  • Mechanical Engineering (AREA)
  • Pyridine Compounds (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US721100A 1958-03-13 1958-03-13 Antifoggants and stabilizers for photographic silver halide emulsions Expired - Lifetime US2948615A (en)

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Application Number Priority Date Filing Date Title
BE576406D BE576406A (enrdf_load_html_response) 1958-03-13
US721100A US2948615A (en) 1958-03-13 1958-03-13 Antifoggants and stabilizers for photographic silver halide emulsions
GB7915/59A GB858326A (en) 1958-03-13 1959-03-06 Antifoggants and stabilizers for photographic silver halide emulsions
DEG26610A DE1106169B (de) 1958-03-13 1959-03-12 Lichtempfindliches photographisches Material

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3446618A (en) * 1965-11-08 1969-05-27 Gaf Corp Photographic silver halide emulsions containing trifluoromethyl - 4 - hydroxy quinoline carboxy acid salt as a stabilizer
US3547638A (en) * 1967-06-20 1970-12-15 Eastman Kodak Co N,n-disubstituted amino-methylthiocarboxylic acids and use thereof as antifoggants in photographic emulsions
US3630745A (en) * 1969-10-08 1971-12-28 Eastman Kodak Co THIAZOLO {8 5,4-c{9 ISOQUINOLINE AND THIAZOLO {8 4,5-c{9 IOSQUINOLINE AND DERIVATIVES AS ANTIFOGGANTS FOR PHOTOGRAPHIC LAYERS
US4009036A (en) * 1973-12-13 1977-02-22 Agfa-Gevaert A.G. Photographic developer
US4416977A (en) * 1981-02-17 1983-11-22 Mitsubishi Paper Mills, Ltd. Silver halide photographic photosensitive material

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5441851A (en) * 1991-11-25 1995-08-15 Eastman Kodak Company Use of heterocyclic nitrogen addenda to reduce continued coupling of magenta dye-forming couplers
US5478721A (en) * 1995-01-31 1995-12-26 Eastman Kodak Company Photographic elements containing emulsion stabilizers

Citations (2)

* 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
US2819965A (en) * 1956-02-23 1958-01-14 Eastman Kodak Co Carboxymethylmercapto compounds as stabilizers for photographic emulsions

Patent Citations (2)

* 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
US2819965A (en) * 1956-02-23 1958-01-14 Eastman Kodak Co Carboxymethylmercapto compounds as stabilizers for photographic emulsions

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3446618A (en) * 1965-11-08 1969-05-27 Gaf Corp Photographic silver halide emulsions containing trifluoromethyl - 4 - hydroxy quinoline carboxy acid salt as a stabilizer
US3547638A (en) * 1967-06-20 1970-12-15 Eastman Kodak Co N,n-disubstituted amino-methylthiocarboxylic acids and use thereof as antifoggants in photographic emulsions
US3630745A (en) * 1969-10-08 1971-12-28 Eastman Kodak Co THIAZOLO {8 5,4-c{9 ISOQUINOLINE AND THIAZOLO {8 4,5-c{9 IOSQUINOLINE AND DERIVATIVES AS ANTIFOGGANTS FOR PHOTOGRAPHIC LAYERS
US4009036A (en) * 1973-12-13 1977-02-22 Agfa-Gevaert A.G. Photographic developer
US4416977A (en) * 1981-02-17 1983-11-22 Mitsubishi Paper Mills, Ltd. Silver halide photographic photosensitive material

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DE1106169B (de) 1961-05-04
BE576406A (enrdf_load_html_response) 1900-01-01
GB858326A (en) 1961-01-11

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