US2691581A - Photographic emulsions sensitized with oxonol dyes containing a 5(4)-thiazolone nucleus - Google Patents

Photographic emulsions sensitized with oxonol dyes containing a 5(4)-thiazolone nucleus Download PDF

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US2691581A
US2691581A US224714A US22471451A US2691581A US 2691581 A US2691581 A US 2691581A US 224714 A US224714 A US 224714A US 22471451 A US22471451 A US 22471451A US 2691581 A US2691581 A US 2691581A
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thiazolone
nucleus
dyes
emulsion
sensitized
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Edward B Knott
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Eastman Kodak Co
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Eastman Kodak Co
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • 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
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes

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  • This invention relates to photographic silver halide emulsions containing sensitizing dyes and to certain new sensitizing dyes.
  • Certain dyes of the cyanine and merocyanine classes are known to alter the sensitivity of pho ⁇ tographic emulsions. Dyes of the oxonol class have also been used for this purpose, but, in general, these dyes have been found to be extremely weak sensitizers. Now I have found that oxonol dyes containing a 2alkylthio5(4) -thiozolone nucleus can advantageously be used to sensitize photographic silver halide emulsions. Some of the dyes of my invention possess sensitzing power approaching that of the merocyanine dyes, which was quite surprising in View of the known deficiencies of oxonol dyes previously employed for this purpose.
  • An object of my invention is to provide photographic silver halide emulsions sensitized with oxonol dyes. Another object is to provide a sup-- port coated with such sensitized emulsions. Still another object is to provide certain new oxonol dyes. A further object is to provide methods for obtaining these new dyes. Other objects will become apparent from a consideration ⁇ of the following description and examples.
  • oxonol dyes useful in practicing my invention can be represented by the following general formula:
  • R represents an alkyl group, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-amyl, n-hexyl, Z-ethylbutyl, n-heptyl,
  • heterocyclic ring such as those selected from the group consisting of a thiozolone nucleus, lfor example, a 2,4(3,5)thiazoledione nucleus, such as 2,4(3,5)thiazoledione, 3ethyl-2,4(3,5)thi azoledione, 3phenyl-2,4(3,5) -thiazoledione or 3naphthyl-2,4(3,5)-thiazoledione nuclei, a 2- thio-2,4(3,5)-thiazoledione (a rhodanine) nudione (3-alkylrhodanine), 3-phenyl-2-thio- 2,4(3,5) -thiazoledione (S-phenylrhodanine) 3- naphthyl-2-thio-2,4(3,5) -thiazoledione (S-naphthylrhodanine) nuclei or 3-(1-benZothiaZyD-2-
  • a 2thio 2,4(3,5)oxazoledione nucleus such as a 3-alkyl- 2-thio2,4(3,5) -oxazoledione nucleus
  • an imidazolone nucleus for example a 2,4(3,5)imidazo1e dione nucleus, such as 2,4(3,5)imidazoledione (hydrantoin) or its S-alkyl, 3-phenyl or Sfnaphthyl derivatives as well as its 1,3-dialkyl, l-alkyl- 3-pheny1, 1alkyl3naphthyL 1,3-diphenyl, etc., derivatives, a 2thio-2,4(3,5)-imidazoledione nucleus, such as 2thio2,4(3,5)-imidazoledione (2- thiohydantoin) or its 3'alkyl, 3-phenyl or 3-nap
  • the dyes wherein Q represents the nonmetallic atoms necessary to complete a heterocyclic nucleus containing ve atoms in the heterocyclic ring, three of said atoms being carbon atoms, one of said atoms being a nitrogen atom, and the other of said atoms being a sulfur atom, a nitrogen atom, or an oxygen atom, have been found to be especially well adapted to the manufacture of photographic emulsions, I have found.
  • oxonol dyes selected. from those represented by Formula I wherein Q represents the nonmetallic atoms necessary to complete a 2-alkylthio-5(4) -thiazolone nucleus, the alkyl group of which is-a long-chain alkyl group, are especially useful in practicing our invention.
  • Such oxonol dyes embraced by Formula I can be represented by the following wherein R has the values set forth above, and fR-i represents an alkyl group, especially a longchain alkyl group, such as n-hexyl, n-heptyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, stearyl, n-eicosanyl, etc. (especially an alkyl group of the formula C11H2n+1 wherein 11. represents a positive integer from 6 to 20.
  • the oxonol dyes represented by Formula I above can advantageously be prepa-red by condensing a 2-alkylthio-5(4)-thiazolone selected from those represented by the following general wherein R has the values set forth above, with a 4-ethoxymethylene compound selected from those represented by the following general formula:
  • R2 represents a hydrogen atom or an alkyl group, such as methyl, ethyl, etc.
  • the condensations can advantageously be carried out in the presence of a basic condensing agent, such as the trialkylamines (e. g. triethylamine, tri-n-propylamine, triisopropylamine, trin-butylamine, triisobutylamine, tri-n-amylamine, etc.), N,Ndialky1anilines (e. g. N,N-dimethylaniline, N,N-diethylaniline, etc), heterocyclic tertiary amines (e. g. N-alkylpiperidines, such as N-methylpiperidine, N -ethy1piperidine, etc., pyridine, quinoline, etc.) etc.
  • a basic condensing agent such as the trialkylamines (e. g. triethylamine, tri-n-propylamine, triisopropylamine, trin-butylamine, triisobutylamine, tri-n
  • Inert solvents can also be employed, if desired.
  • Typical inert solvents include the aliphatic alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, etc., diethyl ether, chloroform, carbontetrachloride, benzene, toluene, Xylenes, n-pentane, n-hexane, n-heptane, 1,4-dioxane, acetone, glycol, etc.
  • Heat accelerates the condensations, and temperatures varying from room temperature (about 25 C.) to the reflux temperature of the reaction mixture can be employed.
  • the intermediates represented by Formula V can advantageously be prepared by intermixing an aqueous alkali metal hydroxide solution, carbon disulfide, and glycine, lfollowed by addition kof an alkyl halide to the alkali metal salt (M-s--NH-CHT-(HJ-OM) formed, heating the mixture at a temperature of from about 40 to V100 C., and acidifying the reaction mixture to give the desired ester represented by Formula V above.
  • These steps can be illustrated by the following general equations:
  • the oxonol dyes represented by Formula I above can be prepared by condensing a vketomethylene compound selected from those represented by the following general formula:
  • R and Rz have the values set forth above.
  • condensations can advantageously be carried out in the presence of a basic condensing agent, such as the trialkylamines (e. g. triethylamine, tri-n-propylamine, triisopropylamine, trin-butylamine, triisobutylamine, tr-n-amylamine, etc.)
  • a basic condensing agent such as the trialkylamines (e. g. triethylamine, tri-n-propylamine, triisopropylamine, trin-butylamine, triisobutylamine, tr-n-amylamine, etc.)
  • N,N-dialkylanilines e. g. N,Ndi methylaniline, N,Ndiethylaniline, etc
  • N-alkylpiperidines e. g. N-methylpiperidine, N-ethylpiperidine, etc.
  • heterocyclic tertiary amines
  • condensations can advantageously be carried out in the presence of an inert diluent, such as the aliphatic alcohols (e. g. methanol, ethanol, isopropanol, n-propanol, n-butanol, isobutanol, etc.) diethyl ether, 1,4-dioxane, chloroform, carbontetrachlcride, benzene, toluene, xylenes, n-pentane, n-hexane, n-heptane, etc.
  • This dye was prepared according to the method of Cook et al. (loc. cit). It sensitized a gelatino silver chloride emulsion with a maximum at 520 m/L and a gelatine silver bromiodide emulsion with a maximum at 540 ma.
  • This dye was prepared according to the method of Cook et al. (loc. cit.). It sensitized a gelatine silver chloride emulsion with a maximum at 540 ma and a gelatine silver bromiodide emulsion with a maximum at 545 ma.
  • 2-n-octythio5(4)-thiazolone obtained by heating together 1.3 g. of Ndthiocarbo-n.oc toxyglycine and cc. of acetic anhydride according to the method described in Example 5 above, 1.2 g. of 2-acetamino5(4) -thiazolone obtained as described in the copending application Serial No. 203,525, filed on December 29, 1950, in the names of Per Aubert and Edward B. Knott), 10 cc. of ethanol, and 3 cc. of triethylamine were heated together for 5 minutes on a boiling water bath.
  • N-thiocarbo-n-tetradecoxyglycine employed in Example 4 was prepared as follows:
  • Example 9 N-thocarbo-n-tetradecomyglycine i HotlJ-oHg-NH-h-o-oHz-(cnme-cm 1 g. mol of tetradecanol was dissolved in 250 cc. of carbondisuliide and 1 g. mol of finely powdered potassium hydroxide added. The Whole was then shaken mechanically until it had set to a solid. After chilling overnight, the salt was collected,
  • This product obtained. above was added to 2250v cc. o' methanol and 1 g. mol. of ethylv bromide added. The reaction mixture was then warmed for several minutes, anddiluted with Water. The aqueous layer was separated and the oil remaining was taken up in diethyl ether. The ether layer was dried over sodium sulfate, and the ether removed. The ethyl n-tetradecoxy xanthate thus formed was used directly in the next step.
  • the N-dithiom-octoxyglycine used in Example 5 was prepared as follows:
  • Example 10 N-dithiocarbo-n-octomyglycine 22.4 g. of potassium hydroxide were dissolved in 50 cc. of Water and the solution chilled. There were then added 15.0 g. of glycine and 15.2 g. of carbondisulfide, and the Whole shaken mechanically until a clear orange solution resulted. A solution of 38.6 g. of n-octylbromide in 50 cc. of ethanol was added, and the mixture heated for 30 minutes on a steam bath. To the resulting one-phase solution there were added 100 cc. of water, and the cloudiness resulting removed by extraction with diethyl ether.
  • the aqueous layer was warmed gently under reduced pressure to expel any dissolved ether, the solution chilled, and acidied with concentrated hydrochloric acid.
  • the precipitate was collected on a filter, washed with Water, air-dried, and recrystallized from petroleum ether (bp. 60-80 C.) as glistening plates melting at 100 C.
  • Example 6 By replacing the n-octyl bromide used in Example 10 by a molecularly equivalent amount of n-dodecyl halide, the N-dithiocarbo-n-dodecoxyglycine used in Example 6 was obtained as glossy plates melting at 111 C. on recrystallization from ligroin.
  • concentration of the dye will vary according to the type of light-sensitive material in the emulsion and according to the eiect desired. The suitable and most economical concentration for any given emulsion will be apparent to those skilled in the art of emulsion making.
  • FIG. 1 is a diagrammatic reproduction of a spectrogram showing the sensitivity of an ordinary gelatino-silver-bromiodide emulsion containing one of my sensitizing dyes.
  • the curve depicts the sensitivity of an ordinary gelatino silver-brorniodide emulsion containing bis-4- (2-benzylthio-5 (4) thiazolone) methineoxonol.
  • Fig. 1 is a diagrammatic reproduction of a spectrogram showing the sensitivity of an ordinary gelatino-silver-bromiodide emulsion containing one of my sensitizing dyes.
  • the curve depicts the sensitivity of an ordinary gelatino silver-brorniodide emulsion containing bis-4- (2-benzylthio-5 (4) thiazolone) methineoxonol.
  • Fig. 1 is a diagrammatic reproduction of a spectrogram showing the sensitivity of an ordinary gelatino-s
  • the curve depicts the sensitivity of an ordinary gelatino-silver-bromiodide emulsion containing [4-(2-benzylthio- 5(4) thiazolone) l [4 (2 phenyl 5(4) oxazclone) l-methineoxonol.
  • the curve depicts the sensitivity of an ordinary gelatinosilver-bromiodide emulsion containing [4-(2- ethylthio 5(4) thiazolone) l [4 (2 n octylthio 5(4) -thiazolone)l methineoxonol,
  • Emulsions sensatized with my thiazolone dyes can be coated on the usual supports of paper, cellulose acetate nlm, glass, polyvinyl acetal resin nlm, metal, etc., in the usual manner.
  • a photographic silver halide emulsion sensitized with at least one oxonol dye selected from those represented by the following general formula:
  • R represents an alkyl group and Q represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing five atoms in the heterocyclic ring, three of said atoms being carbon atoms, one of said atoms being a nitrogen atom, and the other of said atoms being selected from the group consisting of a nitrogen atom, an y'oxygen atom, and a sulfur atom.
  • a photographic silver halide emulsion sensitized with at least one oXonol dye selected from those represented by the following general formula:
  • R represents an alkyl group and Q represents the non-metallic atoms necessary to cornplete a heterocyclic nucleous of the 2acylamino 5 (4) -thiazolone series.
  • a photographic silver halide emulsion sensitized with at least one oxonol dye selected from those represented by the following general formula:
  • R represents an alkyl group and Q represents the non-metallic atoms necessary to complete a heterocyclic nucleous of the 5(4) -oxazolone series.
  • a photographic silver halide emulsion sxensitized with at least one oxonol dye selected from those represented by the following general formula:
  • R and R1 each represents an alkylL group.
  • a photographic silver halide emulsion sensitized with at least one oxonol dye selected from those represented by the following general formula:
  • R represents an alkyl group of the formula CmI-Izmifi wherein m represents a positive integer from l to 20, and Q represents the nonmetallic atoms necessary to complete a heterocyclic nucleus of the 2acylamino-5(4) thiazolone series.
  • a photographic silver halide emulsion sensitized with at least one oxcnol dye selected from those represented by the following general formula:
  • R represents an alkyl group of the formula CMI-12min wherein m represents a positive integer from 1 to 20 and Q represents the nonmetallic atoms necessary to complete a heterocyclic nucleus of the 5(4)-0Xaaolone series.
  • a photographic silver halide emulsion sensitized with at least one oxonol dye selected from those represented by the following general formula:
  • R and R1 each represents an alkyl group vvof the formula Cmll2m+1 wherein m represents a positive integer from l to 20.
  • a photographic silver halide emulsion sensitized with at least one oxonol dye selected from those represented by the following general formula:
  • R-S-t t-Csz (LH, N n lwherein R represents an alkyl group of the formula CmHzmH wherein m represents a positive integer from 1 to 20 and R1 represents an alkyl group of Athe ⁇ formula CnHznH wherein n represents a positive'integer from 6 to 20.
  • a photographic silver chloride emulsion sensitized with at least one oxonol dye selected from those represented by the following general formula:
  • R represents an alkyl group and Q represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing five atoms in the heterocyclic ring, three of said atoms being carbon atoms, one of said atoms being a nitrogen atom, and the other of said atoms being selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom.
  • R represents an alkyl group and Q represents the non-metallic atoms necessary to complete a heterooyclic nucleus containing five atoms in the heterocyclic ring, three of said atoms being carbon atoms, one of said atoms being a nitrogen atom, and the other of said atoms being selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom.
  • a photographic silver halide emulsion sensitized with the oxonol dye having the following formula:
  • a photographic silver halide emulsionsensitized with the oxonol dye having the following formula:
  • a photographic silver halide emulsion sensitized with the oxonol dye having .the following formula:

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US224714A 1951-05-05 1951-05-05 Photographic emulsions sensitized with oxonol dyes containing a 5(4)-thiazolone nucleus Expired - Lifetime US2691581A (en)

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BE511167D BE511167A (en(2012)) 1951-05-05
US224714A US2691581A (en) 1951-05-05 1951-05-05 Photographic emulsions sensitized with oxonol dyes containing a 5(4)-thiazolone nucleus
FR1078930D FR1078930A (fr) 1951-05-05 1952-05-05 émulsions photographiques et colorants applicables en particulier à leur préparation
GB11260/52A GB702247A (en) 1951-05-05 1952-05-05 Oxonol dyes and photographic silver halide emulsions containing them

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2927026A (en) * 1956-08-30 1960-03-01 Eastman Kodak Co Merocyanines and planar undissociated cyanines
US2965486A (en) * 1958-06-02 1960-12-20 Eastman Kodak Co Polymethine sensitizing dyes and photographic emulsions
US3140283A (en) * 1958-10-24 1964-07-07 Gevaert Photo Prod Nv Triarylphosphonium cyclopentadienylide methine dyes and photographic emulsions sensitized therewith
US3540888A (en) * 1967-11-30 1970-11-17 Eastman Kodak Co Photographic silver halide emulsions containing dyes having a 5-alkoxycarbonyl - 2,4 - dioxo-1-aryl-6-thioxopiperidene moiety

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2166736A (en) * 1937-04-23 1939-07-18 Eastman Kodak Co Photographic emulsion
US2177402A (en) * 1935-11-15 1939-10-24 Eastman Kodak Co Dye from thiazolones
US2241238A (en) * 1939-04-29 1941-05-06 Eastman Kodak Co Sensitizing methine dyes and process for preparing them
US2263749A (en) * 1937-04-23 1941-11-25 Eastman Kodak Co Polymethine dyes and process for preparing the same
US2320654A (en) * 1940-08-08 1943-06-01 Riester Oskar Sensitization of photographic emulsions
US2322015A (en) * 1939-05-25 1943-06-15 Eastman Kodak Co Dye and photographic emulsion containing the same
US2338782A (en) * 1940-07-30 1944-01-11 Riester Oskar Cyanine dyestuff
US2340882A (en) * 1935-08-16 1944-02-08 Ilford Ltd Sensitized photographic material
US2353164A (en) * 1944-07-11 Dyestuffs and dyestuff
US2656353A (en) * 1950-12-29 1953-10-20 Eastman Kodak Co Sensitizing dyes containing a 2-thio-2, 5 (3, 4)-thiazoledione nucleus

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2353164A (en) * 1944-07-11 Dyestuffs and dyestuff
US2340882A (en) * 1935-08-16 1944-02-08 Ilford Ltd Sensitized photographic material
US2177402A (en) * 1935-11-15 1939-10-24 Eastman Kodak Co Dye from thiazolones
US2166736A (en) * 1937-04-23 1939-07-18 Eastman Kodak Co Photographic emulsion
US2263749A (en) * 1937-04-23 1941-11-25 Eastman Kodak Co Polymethine dyes and process for preparing the same
US2241238A (en) * 1939-04-29 1941-05-06 Eastman Kodak Co Sensitizing methine dyes and process for preparing them
US2322015A (en) * 1939-05-25 1943-06-15 Eastman Kodak Co Dye and photographic emulsion containing the same
US2338782A (en) * 1940-07-30 1944-01-11 Riester Oskar Cyanine dyestuff
US2320654A (en) * 1940-08-08 1943-06-01 Riester Oskar Sensitization of photographic emulsions
US2656353A (en) * 1950-12-29 1953-10-20 Eastman Kodak Co Sensitizing dyes containing a 2-thio-2, 5 (3, 4)-thiazoledione nucleus

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2927026A (en) * 1956-08-30 1960-03-01 Eastman Kodak Co Merocyanines and planar undissociated cyanines
US2965486A (en) * 1958-06-02 1960-12-20 Eastman Kodak Co Polymethine sensitizing dyes and photographic emulsions
US3140283A (en) * 1958-10-24 1964-07-07 Gevaert Photo Prod Nv Triarylphosphonium cyclopentadienylide methine dyes and photographic emulsions sensitized therewith
US3143544A (en) * 1958-10-24 1964-08-04 Gevaert Photo Prod Nv Triarylphosphonium cyclopentadienylide methine dyes and photographic emulsions sensitized therewith
US3540888A (en) * 1967-11-30 1970-11-17 Eastman Kodak Co Photographic silver halide emulsions containing dyes having a 5-alkoxycarbonyl - 2,4 - dioxo-1-aryl-6-thioxopiperidene moiety

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