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US3312553A - Photographic materials - Google Patents

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Publication number
US3312553A
US3312553A US319969A US31996963A US3312553A US 3312553 A US3312553 A US 3312553A US 319969 A US319969 A US 319969A US 31996963 A US31996963 A US 31996963A US 3312553 A US3312553 A US 3312553A
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US
United States
Prior art keywords
gelatin
emulsion
silver halide
oxide
silver
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Expired - Lifetime
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US319969A
Inventor
Dersch Fritz
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GAF Chemicals Corp
Original Assignee
General Aniline and Film Corp
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Filing date
Publication date
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US319969A priority Critical patent/US3312553A/en
Priority to GB42754/64A priority patent/GB1080058A/en
Priority to DEG41877A priority patent/DE1213735B/en
Priority to FR993185A priority patent/FR1412870A/en
Priority to BE655063D priority patent/BE655063A/xx
Application granted granted Critical
Publication of US3312553A publication Critical patent/US3312553A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • 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
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • G03C1/047—Proteins, e.g. gelatine derivatives; Hydrolysis or extraction products of proteins
    • 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
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • G03C1/043—Polyalkylene oxides; Polyalkylene sulfides; Polyalkylene selenides; Polyalkylene tellurides

Definitions

  • silver halide emulsions were sensitized with certain types of polyoxyalkylene glycols.
  • various derivatives of polyoxyalkylene glycols such as the alkylene oxide adducts of glycols having from 8 to 18 carbon atoms, as well as the oxide adduct of various other active hydrogen-containing compounds such as amines,
  • gelatin a water-soluble polyoxyalkylene derivative of gelatin into a silver halide emulsion. While the exact structure of gelatin is not known, it occurs in bones, hides, skins, and sinews and can be readily obtained from the parent substance, collagen, by wellknown prior art treatments which usually involve some form of treatment such as degreasing in the case of bone stock, and liming or acidulation'in the case of hide and sinew stock, to prepare the raw material for the cooking step.
  • the above treated raw material is hydrolyzed into gelatin by heating in water to yield a solution which is concentrated by vacuum evaporation and subsequently spray or drum dried to product a gelatin product recovcrable as sheets, flakes, powder, pearls or noodles depending on the mode of processing.
  • gelatin Any form of gelatin appears operable for the formation of the water-soluble oxide adducts thereof which are employed in the photographic materials of the invention.
  • alkylene oxides which find immediate and practical applicability in producing the water-soluble polyoxyalkylene derivatives of gelatin include representative compounds such as ethylene oxide, propylene oxide, butylene oxide, styrene oxide, cyclohexene oxide with the vic epoxides being preferred.
  • the p-olyoxyalkylene derivatives of gelatin which are employed as sensitizers for silver halide emulsions are prepared simply by reacting gelatin with an alkylene oxide.
  • the reaction between gelatin and an alkylene oxide is conveniently carried out simply by heating one part of gelatin with from 0.8 to 5 parts of alkylene oxide at atemperature from to 200 C. in the presence of a catalyst.
  • the catalysts which can be employed are the alkoxides, oxides, and hydroxides of lithium, potassium, sodium, calcium, zinc. and lead.
  • the preferred catalysts are the alkali metal hydroxides, particularly sodium hydroxide and potassium hydroxide.
  • the amount of water soluble polyoxyalkylene derivatives of gelatin which are incorporated into the silver halide emulsions is not narrowly critical and can vary over a wide range, depending on the amount of silver halide which is used as the sensitizer. Thus, it has been found that from .5 to 50 grams of said polyoxylene derivatives of gelatin per .4 mol of silver halide may be employed.
  • the polyoxyalkylene derivatives of gelatin may be incorporated into various kinds of photographic emulsions. In addition to being useful inordinary non-sensitized emulsions, they may also be used in orthochromatic, panchromatic, and X-ray emulsions. If used with sensitizing dyes, they may be added to the emulsion before or after the dyes are added. Various silver salts may be used as the sensitive salt, such as silver bromide, silver iodide, silver chloride, or mixed silver halide.
  • the polyoxyethylene derivatives of gelatin may be used in emulsions intended for color photography, such as emulsions containing color forming agents or emulsions containing color couplers.
  • the dispersing agent in the photo-graphic emulsion may be gelatin or other colloids, such as collodion, albumen, cellulse derivatives i.e., carb-oxymethylcellulose, polyvinyl alcohol, polvinylpyrrolidone, or the ike.
  • colloids such as collodion, albumen, cellulse derivatives i.e., carb-oxymethylcellulose, polyvinyl alcohol, polvinylpyrrolidone, or the ike.
  • the increase of effective sensitivity of photographic silver halide emulsions with the polyoxyalkylene derivatives of gelatin can be obtained in a number of ways. Thus they may be added to an undercoating, to a middle coating, to an overcoating or to a surface coating prior to the coating operation. Additionally, if so desired, they maybe added during the actual preparation of the emulsion either before or after Washing the emulsion.
  • gelatin-alkylene oxide adducts not only contribute to the photolytic properties of the silver halide emulsion, they also operate to greatly increase its covering power. This expedites coating of the emulsion on the selected base on which it is laid down. It also permits use of less silver halide than would normally be required.
  • Example I A 30% gelatin solution in water is prepared. While the temperature is held at 40 C. ethylene oxide is passed through this solution for 20 minutes. The resulting product had lower gelatin strength and the melting point dropped from 39 C. to 365 C.
  • Example II A silver halide emulsion in gelatin containing 4% silver iodide and 96% silver bromide was prepared in a conventional manner and brought up to its maximum light sensitivity. It was then readied for coating on film base by melting it at 40 C. and incorporating coating finals such as sensitizing dyes, stabilizers, and hardeners.
  • a 10% aqueous solution of a polyoxyethylene deriva- .tive of gelatin was prepared by reacting one part of gelatin with two parts of ethylene oxide and heating said mixture at 100 C. in the presence of sodium hydroxide. Thirty cubic centimeters of this solution was added to a sample of the above described silver halide emulsion that contained about 0.4 mole of silver halide.
  • the emulsion samples are then coated on a suitable cellulose ester base and dried.
  • the film samples are exposed in a type 13 sensitometer and developed in a developer having the following composition:
  • Example III A silver halide emulsion in gelatin containing 4% silver iodide and 96% silver bromide was coated on a film base in a conventional manner. After the coating, an aqueous gelatin solution containing 20 grams of gelatin per liter and 30 grams of a po lyoxyethylene derivative of gelatin prepared in the same manner as disclosed in Example I was mixed and coated on the film base as an antia'brasion layer. After drying, film samples were exposed and processed as disclosed in Example H. The samples described exhibited a relative speed of 200 with a fog of .14 as compared with a type coating of the same emulsion having an antiabrasion layer similar to that described above, but lacking the speed increasing additive and having a speed of and a fog of .10.
  • a lightsensitive silver halide emulsion sensitized with a water-soluble polyoxyalkylene derivative of gelatin resulting from the reaction of gelatin with an alkylene oxide.
  • composition as defined in claim 1 wherein the silver halide emulsion is a silver chloride emulsion.
  • composition as defined in claim 1 wherein the silver halide emulsion is a mixed silver bromide-silver iodide emulsion.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Polyethers (AREA)

Description

United States Patent Patented Apr. 4, 1967 lice 3,312,553 PHOTOGRAPHIC MATERIALS Fritz Dersch, Binghamton, N.Y., assignor to General Aniline & Film Corporation, New York, N.Y., a corporation of Delaware No Drawing. Filed Oct. 30, 1963, Ser. No. 319,969 8 Claims. (Cl. 96-107) The present invention relates to photographic materials of increased sensitivity and covering power which have incorporated therein a water soluble oxide adduct of gelatin.
Previously, according to heretofore customary practices, silver halide emulsions were sensitized with certain types of polyoxyalkylene glycols. Also, various derivatives of polyoxyalkylene glycols, such as the alkylene oxide adducts of glycols having from 8 to 18 carbon atoms, as well as the oxide adduct of various other active hydrogen-containing compounds such as amines,
ethers, esters and amides, have been employed to increase the sensitivity of silver halide emulsions.
However, the silver halide emulsions which were sensitized by the addition of alkylene oxide derivatives of the prior art suffered from many disadvantages which limited their use in photographic processes. Although the silver halide emulsions which had been sensitized in this manner did show a considerable increase in speed, their effectiveness was limited because of their tendency to fog during storage, particularly at elevated temperatures and humidities. Conventional antifoggants were incapable of controlling this fogging tendency and hence it was necessary to resort to special expensive antifoggants to attain this end. (See for example United States Patents 2,704,716, 2,716,062 and 2,728,666.)
Therefore, it is a primary object of this invention to provide a novel sensitized silver halide photographic emulsion, said emulsion having high photographic speed and not subject to excessive fogging during prolonged periods of storage at high humidities.
It is still another object of this invention to provide a novel sensitized silver halide emulsion which does not require the use of excessive and expensive fogging agents in order to be able to store it for relatively long periods of time.
Other objects of this invention will appear from the description of the invention.
It has now been found that the above objects can be obtained by incorporating a water-soluble polyoxyalkylene derivative of gelatin into a silver halide emulsion. While the exact structure of gelatin is not known, it occurs in bones, hides, skins, and sinews and can be readily obtained from the parent substance, collagen, by wellknown prior art treatments which usually involve some form of treatment such as degreasing in the case of bone stock, and liming or acidulation'in the case of hide and sinew stock, to prepare the raw material for the cooking step. The above treated raw material is hydrolyzed into gelatin by heating in water to yield a solution which is concentrated by vacuum evaporation and subsequently spray or drum dried to product a gelatin product recovcrable as sheets, flakes, powder, pearls or noodles depending on the mode of processing.
Any form of gelatin appears operable for the formation of the water-soluble oxide adducts thereof which are employed in the photographic materials of the invention.
The alkylene oxides which find immediate and practical applicability in producing the water-soluble polyoxyalkylene derivatives of gelatin include representative compounds such as ethylene oxide, propylene oxide, butylene oxide, styrene oxide, cyclohexene oxide with the vic epoxides being preferred.
The p-olyoxyalkylene derivatives of gelatin which are employed as sensitizers for silver halide emulsions are prepared simply by reacting gelatin with an alkylene oxide. The reaction between gelatin and an alkylene oxide is conveniently carried out simply by heating one part of gelatin with from 0.8 to 5 parts of alkylene oxide at atemperature from to 200 C. in the presence of a catalyst. The catalysts which can be employed are the alkoxides, oxides, and hydroxides of lithium, potassium, sodium, calcium, zinc. and lead. The preferred catalysts are the alkali metal hydroxides, particularly sodium hydroxide and potassium hydroxide.
The amount of water soluble polyoxyalkylene derivatives of gelatin which are incorporated into the silver halide emulsions is not narrowly critical and can vary over a wide range, depending on the amount of silver halide which is used as the sensitizer. Thus, it has been found that from .5 to 50 grams of said polyoxylene derivatives of gelatin per .4 mol of silver halide may be employed.
The polyoxyalkylene derivatives of gelatin may be incorporated into various kinds of photographic emulsions. In addition to being useful inordinary non-sensitized emulsions, they may also be used in orthochromatic, panchromatic, and X-ray emulsions. If used with sensitizing dyes, they may be added to the emulsion before or after the dyes are added. Various silver salts may be used as the sensitive salt, such as silver bromide, silver iodide, silver chloride, or mixed silver halide. The polyoxyethylene derivatives of gelatin may be used in emulsions intended for color photography, such as emulsions containing color forming agents or emulsions containing color couplers. Additionally, the dispersing agent in the photo-graphic emulsion may be gelatin or other colloids, such as collodion, albumen, cellulse derivatives i.e., carb-oxymethylcellulose, polyvinyl alcohol, polvinylpyrrolidone, or the ike. g
It has also been determined that the increase of effective sensitivity of photographic silver halide emulsions with the polyoxyalkylene derivatives of gelatin can be obtained in a number of ways. Thus they may be added to an undercoating, to a middle coating, to an overcoating or to a surface coating prior to the coating operation. Additionally, if so desired, they maybe added during the actual preparation of the emulsion either before or after Washing the emulsion.
Strangely enough, the gelatin-alkylene oxide adducts not only contribute to the photolytic properties of the silver halide emulsion, they also operate to greatly increase its covering power. This expedites coating of the emulsion on the selected base on which it is laid down. It also permits use of less silver halide than would normally be required.
The following examples will illustrate the instant invention, but it is to be understood that it is not intended that it be limited thereto.
Example I A 30% gelatin solution in water is prepared. While the temperature is held at 40 C. ethylene oxide is passed through this solution for 20 minutes. The resulting product had lower gelatin strength and the melting point dropped from 39 C. to 365 C.
Example II A silver halide emulsion in gelatin containing 4% silver iodide and 96% silver bromide was prepared in a conventional manner and brought up to its maximum light sensitivity. It was then readied for coating on film base by melting it at 40 C. and incorporating coating finals such as sensitizing dyes, stabilizers, and hardeners.
A 10% aqueous solution of a polyoxyethylene deriva- .tive of gelatin was prepared by reacting one part of gelatin with two parts of ethylene oxide and heating said mixture at 100 C. in the presence of sodium hydroxide. Thirty cubic centimeters of this solution was added to a sample of the above described silver halide emulsion that contained about 0.4 mole of silver halide. A sample of the same emulsion, but not containing the gelatin adduct, served as a control. The emulsion samples are then coated on a suitable cellulose ester base and dried. The film samples are exposed in a type 13 sensitometer and developed in a developer having the following composition:
Grams Metol V V 1.5 Sodium sulfite anhydrous 45.0 Sodium bisulfite 1.0 Hydroquinone 3.0 Sodium carbonate monohydrate 6.8 Potassium bromide 0.8 Water to make 1 liter.
The results obtained were as follows:
Fog
Relative Speed After 12 6 Days Dev. Oven and 4 Dev.
Quantity of Ethylene Oxide Adduct of Gelatin:
100 .10 .08 3 grams 150 .12 .09 Quantity of Polyoxyethylene Laurylether Added, 1 gram 150 .28 .16
Example III A silver halide emulsion in gelatin containing 4% silver iodide and 96% silver bromide was coated on a film base in a conventional manner. After the coating, an aqueous gelatin solution containing 20 grams of gelatin per liter and 30 grams of a po lyoxyethylene derivative of gelatin prepared in the same manner as disclosed in Example I was mixed and coated on the film base as an antia'brasion layer. After drying, film samples were exposed and processed as disclosed in Example H. The samples described exhibited a relative speed of 200 with a fog of .14 as compared with a type coating of the same emulsion having an antiabrasion layer similar to that described above, but lacking the speed increasing additive and having a speed of and a fog of .10.
Various modifications of the invention as set forth in the preceding examples will become evident to those skilled in the art such as the use of equivalent materials not necessarily disclosed in the specification. It is not intended, therefore, that the invention .be limited except as necessitated by the appended claims.
What is claimed is:
1. A lightsensitive silver halide emulsion sensitized with a water-soluble polyoxyalkylene derivative of gelatin resulting from the reaction of gelatin with an alkylene oxide.
2. The composition as defined in claim 1 wherein the silver halide emulsion is a silver chloride emulsion.
3. The composition as defined in claim 1 wherein the silver halide emulsion is a mixed silver bromide-silver iodide emulsion.
.4. The emulsion of claim 1 wherein the alkylene oxide is ethylene oxide.
5. The emulsion of claim 1 where the alkylene oxide is propylene oxide.
6. The emulsion of claim 1 wherein the alkylene oxide is butylene oxide.
7. The emulsion of claim 1 wherein the alkylene oxide is styrene oxide.
8. The emulsion of claim 1 wherein the alkylene oxide is cyclohexene oxide.
References Cited by the Examiner UNITED STATES PATENTS 2,380,280 7/1945 Weyerts 96-107 2,494,041 1/1950 Frame 260117 2,848,330 8/1958 Chechak et a1. 96-107 2,900,267 8/1959 Cavanau'gh et a1. '2601l7 3,047,394 7/1962 Allen et al. 96--111 3,061,436 10/1962 Himmelmann 96111 3,091,537 5/1963 Burness 96l.11
NORMAN G. TORCHIN, Primary Examiner.
A. E. TANENHOLTZ, Assistant Examiner.

Claims (1)

1. A LIGHT-SENSITIVE SILVER HALIDE EMULSION SENSITIZED WITH A WATER-SOLUBLE POLYOXYALKYLENE DERIVATIVE OF GELATIN RESULTING FROM THE REACTION OF GELATIN WITH AN ALKYLENE OXIDE.
US319969A 1963-10-30 1963-10-30 Photographic materials Expired - Lifetime US3312553A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US319969A US3312553A (en) 1963-10-30 1963-10-30 Photographic materials
GB42754/64A GB1080058A (en) 1963-10-30 1964-10-20 Photographic silver halide emulsions
DEG41877A DE1213735B (en) 1963-10-30 1964-10-28 Photosensitive photographic silver halide emulsion sensitized with alkylene oxide adducts
FR993185A FR1412870A (en) 1963-10-30 1964-10-29 Improvements to photographic materials
BE655063D BE655063A (en) 1963-10-30 1964-10-30

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DE (1) DE1213735B (en)
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GB (1) GB1080058A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3617284A (en) * 1966-09-19 1971-11-02 Agfa Gevaert Nv Development process for lith-type emulsion with n-vinyl 2-pyrrolidone polymer
US3923517A (en) * 1973-02-15 1975-12-02 Fuji Photo Film Co Ltd Method for rapidly forming photographic images
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
EP0768570A1 (en) 1995-10-09 1997-04-16 Konica Corporation Image forming method
WO2005072974A1 (en) 2004-01-16 2005-08-11 Eastman Kodak Company Mordanted inkjet recording element and printing method
WO2012035314A1 (en) 2010-09-17 2012-03-22 Fujifilm Manufacturing Europe Bv Photographic paper
WO2021213762A1 (en) 2020-04-24 2021-10-28 Fujifilm Manufacturing Europe Bv Photographic paper

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2380280A (en) * 1943-03-06 1945-07-10 Eastman Kodak Co Chemical sensitizing of emulsions
US2494041A (en) * 1947-08-13 1950-01-10 Eastman Kodak Co Derivatives obtained by reacting gelatin and furoyl halides
US2848330A (en) * 1955-12-01 1958-08-19 Eastman Kodak Co Photographic emulsions sensitized with sulfonium salts and alkylene oxide polymers
US2900267A (en) * 1956-10-17 1959-08-18 Armour & Co Modified animal glue and method of preparation
US3047394A (en) * 1958-08-01 1962-07-31 Eastman Kodak Co Photosensitive products containing therein layers hardened by bisepoxides
US3061436A (en) * 1958-12-06 1962-10-30 Agfa Ag Vinylsulfonamide modified gelatine and photographic emulsions therefrom
US3091537A (en) * 1959-05-04 1963-05-28 Eastman Kodak Co Hardening of photographic layers

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2380280A (en) * 1943-03-06 1945-07-10 Eastman Kodak Co Chemical sensitizing of emulsions
US2494041A (en) * 1947-08-13 1950-01-10 Eastman Kodak Co Derivatives obtained by reacting gelatin and furoyl halides
US2848330A (en) * 1955-12-01 1958-08-19 Eastman Kodak Co Photographic emulsions sensitized with sulfonium salts and alkylene oxide polymers
US2900267A (en) * 1956-10-17 1959-08-18 Armour & Co Modified animal glue and method of preparation
US3047394A (en) * 1958-08-01 1962-07-31 Eastman Kodak Co Photosensitive products containing therein layers hardened by bisepoxides
US3061436A (en) * 1958-12-06 1962-10-30 Agfa Ag Vinylsulfonamide modified gelatine and photographic emulsions therefrom
US3091537A (en) * 1959-05-04 1963-05-28 Eastman Kodak Co Hardening of photographic layers

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3617284A (en) * 1966-09-19 1971-11-02 Agfa Gevaert Nv Development process for lith-type emulsion with n-vinyl 2-pyrrolidone polymer
US3923517A (en) * 1973-02-15 1975-12-02 Fuji Photo Film Co Ltd Method for rapidly forming photographic images
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
EP0768570A1 (en) 1995-10-09 1997-04-16 Konica Corporation Image forming method
WO2005072974A1 (en) 2004-01-16 2005-08-11 Eastman Kodak Company Mordanted inkjet recording element and printing method
WO2012035314A1 (en) 2010-09-17 2012-03-22 Fujifilm Manufacturing Europe Bv Photographic paper
WO2021213762A1 (en) 2020-04-24 2021-10-28 Fujifilm Manufacturing Europe Bv Photographic paper

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Publication number Publication date
FR1412870A (en) 1965-10-01
GB1080058A (en) 1967-08-23
BE655063A (en) 1965-02-15
DE1213735B (en) 1966-03-31

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