US3507660A - Photographic materials containing long-chain alkyl sucrose urethane - Google Patents

Photographic materials containing long-chain alkyl sucrose urethane Download PDF

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Publication number
US3507660A
US3507660A US510090A US3507660DA US3507660A US 3507660 A US3507660 A US 3507660A US 510090 A US510090 A US 510090A US 3507660D A US3507660D A US 3507660DA US 3507660 A US3507660 A US 3507660A
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photographic
gelatin
urethane
emulsion
coating
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US510090A
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Fukihiko Nishio
Masakazu Yoneyama
Yoshinori Tuchiya
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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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
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/30—Hardeners
    • G03C1/303—Di- or polysaccharides

Definitions

  • a gelatin containing photographic composition and a photographic light-sensitive element are disclosed.
  • the composition contains from .05 to 100 g. per 1 kg. of dry gelatin of one of the following compounds:
  • the element contains a support and a photographic silver halide emulsion layer and the emulsion contains the above compound.
  • the present invention relates to photography and, more particularly to a gelatin-containing photographic material mainly composed of gelatin for photographic films or photographic papers, said material containing a longchain alkyl sucrose ether or urethane.
  • a gelatin-containing photographic material mainly composed of gelatin for photographic films or photographic papers, said material containing a longchain alkyl sucrose ether or urethane.
  • an object of this invention is to provide an improved gelatin-containing solution having improved coating property.
  • Another object of this invention is to provide a photographic emulsion or a gelatin composition not accompanied by repellences and other coating troubles.
  • An additional object of this invention is to provide a photographic gelatin layer on which a second gelatin layer can be easily coated by applying both layers on a support through separate coating means or by simultaneously applying them on a substratum cooled in a wet state.
  • a further object of this invention is to provide an antistatic effect in the case of coating a coating solution upon a film support.
  • a still further object of this invention is to provide a coating process while maintaining a coating solution stable, such that no precipitates are formed even in the case of melting at a high temperature.
  • the inventors have found that these objects can be achieved by adding in a coating solution a long chain alkyl sucrose ether or urethane.
  • the surface active agent in this invention may be added in a photographic coating solution in an amount of 0.05 g. per 1 kg. of dried gelatin, and preferably in an amount of 0.1-50 g.
  • the surface active agent By the addition of the surface active agent, the surface tension of the coating solution is remarkably lowered, the coating solution becomes free of bubbles, and extremely uniform coating can be obtained not only by usual-speed coating, but also by high-speed coating. Further, if a large amount of the surface active agent is incorporated in a photographic emulsion, it does not give yellow fogging which is inevitably accompanied with the use of other conventional nonionic surface active agents. It also does not have a bad influence on the photographic properties. Furthermore, the surface active agent of the invention may be used together with other known surface active agents.
  • Example 1 A silver bromochloride photographic emulsion containing 7% gelatin and 5% silver halide was prepared. Into the thus prepared photographic emulsion was added the monododecyl ether or sucrose in an amount of 0.5 g. per 1 kg. of emulsion. The photographic emulsion was coated on a baryta paper and set by cooling without drying. On the thus coated layer there was coated a gelatin solution containing di-2-ethylhexyl sodium sulfosuccinate in an amount of 0.2 gin 1 l. of the 2.5 gelatin solution and it was dried after setting by cooling. The thus obtained photographic emulsion layer and the protective film layer were satisfactory. That is, no bubbles were observed in either the photographic emulsion layer or the protective film layer, and they could be applied at a high speed as compared with that by usual coating method.
  • Example 2 Coating was conducted in the same manner as in Example l, but using sucrose monodecyl urethane as the surface active agent. This case gave satisfactory results as in Example 1.
  • Example 3 A silver bromo-chloride photographic emulsioncontaining 7% gelatin and 5% silver halides was prepared. Into the photographic emulsion was added sucrose monododecyl urethane varying the amount in a range of 0.1- 3.2 g. per 1 kg. of photographic emulsion. In this case, the sucrose monodecyl urethane was added as a 2% aqueous solution. The emulsion was coated on a baryta paper and dried.
  • Example 4 The procedure as in Example 3 was repeated using sucrose monodecyl ether, which showed as in Example 3, that the number of repellences and oil spots is remarkably reduced as the amount of the surface active agent is increased.
  • a number in the parenthesis represents the number of oil spots in 10 sq. m. and a number outside the parenthesis represents the number of repellences in 10 sq. m.
  • Example 6 A high-sensitivity photographic emulsion for X-ray photography containing 7% gelatin and 6% silver iodobromide was prepared. Into the photographic emulsion was added sucrose mono-dodecyl urethane in an amount of 0.2 g. per 1 kg. of emulsion. The photographic emulsion was coated on a triacetyl cellulose support and, without drying, was set by cooling. On the thus formed layer there was applied a gelatin solution containing sodium long-chain alkylbenzene sulfonate in an amount of 0.1 g. per 1 l. of a 2.5% gelatin solution and, after setting by cooling, the coating was dried. In this case, no bubbles were observed in both photographic emulsion layer and protective layer. Also, the coatings were applied with a sufficient speed. Moreover, the photographic film obtained by this process has very excellent anti-static properties.
  • R represents an alkyl group having from 7 to 16 carbon atoms.
  • gelatin-containing photographic composition as claimed in claim 1 wherein said compound is contained in said composition in an amount of from about 0.05 to g. per 1 kg. of dry gelatin.
  • gelatin-containing photographic composition as claimed in claim 1 wherein said compound is contained in said composition in an amount of from about 0.1 to 50 g. per 1 kg. of dry gelatin.
  • gelatin-containing photographic composition as claimed in claim 1 wherein said photographic compo sition is a photographic silver halide gelatin emulsion.
  • gelatin-containing photographic composition as claimed in claim 1 wherein said photographic composition is a protective coating composition.
  • a photographic light-sensitive element comprising 6 wherein R represents an alkyl group having from 7 to 16 support and a photographic silver halide emulsion layer carbon atoms.
  • a photographic light-sensitive element comprising a. support, a photographic silver halide emulsion layer, and a protective layer containing gelatin, at least one of said layers containing the compound:

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Laminated Bodies (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Paper (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)

Description

United States Patent PHOTOGRAPHIC MATERIALS CONTAINING LONG-CHAIN ALKYL SUCROSE URETHANE Fukihiko Nishio, Masakazu Yoneyama, and Yoshinori Tuchiya, Ashigara-Kamigun, Kanagawa, Japan, assignors to Fuji Shashin Film Kabushiki Kaisha, Ashigara- Kamigun, Kanagawa, Japan No Drawing. Filed Nov. 26, 1965, Ser. No. 510,090 Claims priority, application Japan, Nov. 26, 1964,
Int. Cl. G03c 1/38 US. Cl. 96114.5 7 Claims ABSTRACT OF THE DISCLOSURE A gelatin containing photographic composition and a photographic light-sensitive element are disclosed. The composition contains from .05 to 100 g. per 1 kg. of dry gelatin of one of the following compounds:
CHQOR O H H HOHzC wherein R is an alkyl group of from 7 to 16 carbon atoms. The element contains a support and a photographic silver halide emulsion layer and the emulsion contains the above compound.
The present invention relates to photography and, more particularly to a gelatin-containing photographic material mainly composed of gelatin for photographic films or photographic papers, said material containing a longchain alkyl sucrose ether or urethane. By incorporating such a surface active agent as mentioned above in a photographic gelatin layer, that is, a photographic emulsion layer and/ or a protective layer, the wetting property of the layer with the surface of a support can be improved and uniform coating can be formed on the support.
It has been variously reported to add natural or synthetic surface active agents in various photographic coating solutions to improve the properties thereof. However, there is trouble in the case of adding natural surface active agents that the quality of the surface active agent is not always constant. On the other hand, it has been reported that by the addition of conventionally known surface active agents, various advantages can be obtained besides improving the wetting property. That is, an antistatic property is endowed, the photographic processing solution can be easily diffused, the troubles caused by water drops can be reduced, air bubbles formed in the case of applying a gelatin sol on a cold-set emulsion surface can be extinguished, development can be accelerated, and staining of a support by a halation preventing dye can be prevented. However, since almost all of the synthetic surface active agents are very peculiar to these actions, although they are effective for some specific photographic emulsions or gelatin compositions, they are sometimes useless to other compositions for improving wetability or preventing the formation of repellances. Therefore, most of the synthetic surface active agents can be used only within a restricted range of use. For these reasons, there have been provided uses of many different types of surface active agents for photography.
One of the most difficult problems is uniformly coating colloidal silver suspended in a diluted gelatin solution. In this case, it is considered to be impossible to obtain a uniform suspension of colloidal silver and to coat it on surfaces without the formation of bubbles and repellences.
Therefore, an object of this invention is to provide an improved gelatin-containing solution having improved coating property.
Another object of this invention is to provide a photographic emulsion or a gelatin composition not accompanied by repellences and other coating troubles.
An additional object of this invention is to provide a photographic gelatin layer on which a second gelatin layer can be easily coated by applying both layers on a support through separate coating means or by simultaneously applying them on a substratum cooled in a wet state.
A further object of this invention is to provide an antistatic effect in the case of coating a coating solution upon a film support.
A still further object of this invention is to provide a coating process while maintaining a coating solution stable, such that no precipitates are formed even in the case of melting at a high temperature.
These and other objects of this invention will become clear in view of the following descriptions.
The inventors have found that these objects can be achieved by adding in a coating solution a long chain alkyl sucrose ether or urethane.
It is considered that the above long-chain monoalkylsucrose ether and urethane can be shown by the following general formula:
onion 0 H H H Home 0 H H OH HO OH H omoH i i OH H H OH (IDHaOCNHR H H H Homo 0 H H OH HO OH 0 l I CHzOH l H OH H H OH wherein R represents an alkyl group containing from 7 to 16 carbon atoms. In this case, if the carbon number is less than 7, the compound has no surface-active property and, if the carbon number is higher than 16, the compound becomes insoluble in water. In both cases the objects of this invention become unattainable.
The surface active agent in this invention may be added in a photographic coating solution in an amount of 0.05 g. per 1 kg. of dried gelatin, and preferably in an amount of 0.1-50 g.
By the addition of the surface active agent, the surface tension of the coating solution is remarkably lowered, the coating solution becomes free of bubbles, and extremely uniform coating can be obtained not only by usual-speed coating, but also by high-speed coating. Further, if a large amount of the surface active agent is incorporated in a photographic emulsion, it does not give yellow fogging which is inevitably accompanied with the use of other conventional nonionic surface active agents. It also does not have a bad influence on the photographic properties. Furthermore, the surface active agent of the invention may be used together with other known surface active agents.
Example 1 A silver bromochloride photographic emulsion containing 7% gelatin and 5% silver halide was prepared. Into the thus prepared photographic emulsion was added the monododecyl ether or sucrose in an amount of 0.5 g. per 1 kg. of emulsion. The photographic emulsion was coated on a baryta paper and set by cooling without drying. On the thus coated layer there was coated a gelatin solution containing di-2-ethylhexyl sodium sulfosuccinate in an amount of 0.2 gin 1 l. of the 2.5 gelatin solution and it was dried after setting by cooling. The thus obtained photographic emulsion layer and the protective film layer were satisfactory. That is, no bubbles were observed in either the photographic emulsion layer or the protective film layer, and they could be applied at a high speed as compared with that by usual coating method.
Example 2 Coating was conducted in the same manner as in Example l, but using sucrose monodecyl urethane as the surface active agent. This case gave satisfactory results as in Example 1.
Example 3 A silver bromo-chloride photographic emulsioncontaining 7% gelatin and 5% silver halides was prepared. Into the photographic emulsion was added sucrose monododecyl urethane varying the amount in a range of 0.1- 3.2 g. per 1 kg. of photographic emulsion. In this case, the sucrose monodecyl urethane was added as a 2% aqueous solution. The emulsion was coated on a baryta paper and dried. The number of repellences and oil spots on thus obtained emulsion-coated photographic papers were investigated in various concentrations of the surface active agent and the results are shown in the following table, which shows that the numbers of repellences and oil spots are aflFectively reduced by an increase in the addition amount of the surface active agent.
Concentration of the surface active agent Number of repellences Number of oil spots in emulsion (g.lkg.) (No./1O sq. m.) (No./10 sq. m.)
Example 4 The procedure as in Example 3 was repeated using sucrose monodecyl ether, which showed as in Example 3, that the number of repellences and oil spots is remarkably reduced as the amount of the surface active agent is increased.
Example 5 S.D.S., gJkg. Em.
s.M.D.U., g./kg. Em. 2 4 s 16 32 In the preceding table, a number in the parenthesis represents the number of oil spots in 10 sq. m. and a number outside the parenthesis represents the number of repellences in 10 sq. m.
From the above results is was found that the surface properties of the coated baryta papers were very improved in the range of the balance of the addition amounts (S.M.D.U.:S.D.S.) being 3 :1 to 8:1.
Example 6 A high-sensitivity photographic emulsion for X-ray photography containing 7% gelatin and 6% silver iodobromide was prepared. Into the photographic emulsion was added sucrose mono-dodecyl urethane in an amount of 0.2 g. per 1 kg. of emulsion. The photographic emulsion was coated on a triacetyl cellulose support and, without drying, was set by cooling. On the thus formed layer there was applied a gelatin solution containing sodium long-chain alkylbenzene sulfonate in an amount of 0.1 g. per 1 l. of a 2.5% gelatin solution and, after setting by cooling, the coating was dried. In this case, no bubbles were observed in both photographic emulsion layer and protective layer. Also, the coatings were applied with a sufficient speed. Moreover, the photographic film obtained by this process has very excellent anti-static properties.
What is claimed is:
1. A gelatin-containing photographic composition containing the compound:
II CHzOCNHR HzC 0 H e e HO OH H 011.011
OH H
HOH
wherein R represents an alkyl group having from 7 to 16 carbon atoms.
2. The gelatin-containing photographic composition as claimed in claim 1 wherein said compound is contained in said composition in an amount of from about 0.05 to g. per 1 kg. of dry gelatin.
3. The gelatin-containing photographic composition as claimed in claim 1 wherein said compound is contained in said composition in an amount of from about 0.1 to 50 g. per 1 kg. of dry gelatin.
4. The gelatin-containing photographic composition as claimed in claim 1 wherein said photographic compo sition is a photographic silver halide gelatin emulsion.
5. The gelatin-containing photographic composition as claimed in claim 1 wherein said photographic composition is a protective coating composition.
6. A photographic light-sensitive element comprising 6 wherein R represents an alkyl group having from 7 to 16 support and a photographic silver halide emulsion layer carbon atoms.
containing the compound: References Cited H UNITED STATES PATENTS CHZOCNR 5 3,170,915 2/1965 Gaertner 252 451 l 3,220,847 11/1965 Knox et al 96-94 H H H HOHZG O 3,300,413 1/1967 Ames 252 -351 3,314,936 4/1967 Ames 252 351 HO OH H 1 011201:
\I 6 H FOREIGN PATENTS H OH 642,936 7/1964 Belgium. wherein R represents an alkyl group having from 7 to 16 OTHER REFERENCES carobn atoms.
7. A photographic light-sensitive element comprising a. support, a photographic silver halide emulsion layer, and a protective layer containing gelatin, at least one of said layers containing the compound:
V. R. Gaertner: Journal of the American Oil Chemists Society, Sucrose Ether and Ester-Linked Surfactants,
VOl. 38, 1961, pp. 410-418.
Chem. Absts., vol. 64, 1966, 17702 f. Chem. Absts., vol. 60, 1964, 9350 c.
o 0112011161116 20 NORMAN G. TORCHIN, Primary Examiner MARY F. KELLEY, Assistant Examiner
US510090A 1964-11-26 1965-11-26 Photographic materials containing long-chain alkyl sucrose urethane Expired - Lifetime US3507660A (en)

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JP6628064 1964-11-26
JP6673564 1964-11-28

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
EP0549496A1 (en) * 1991-12-24 1993-06-30 Eastman Kodak Company Glycoside surfactants as coating aids for photographic layers
US5582963A (en) * 1994-10-28 1996-12-10 Fuji Photo Film Co., Ltd. Process for preparation of silver halide photographic material having emulsion layer and antistatic backing layer
US6071688A (en) * 1998-07-29 2000-06-06 Eastman Kodak Company Providing additives to a coating composition by vaporization
US6153034A (en) * 1997-08-03 2000-11-28 Micromod R.P. Ltd Rapid prototyping
US7250202B1 (en) 1998-06-18 2007-07-31 Ilford Imaging Ch Gmbh Recording sheets for ink jet printing

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59188641A (en) 1983-04-11 1984-10-26 Fuji Photo Film Co Ltd Silver halide photographic emulsion
US5358831A (en) * 1990-12-13 1994-10-25 Eastman Kodak Company High dye stability, high activity, low stain and low viscosity small particle yellow dispersion melt for color paper and other photographic systems
EP2619628B1 (en) 2010-09-17 2014-03-26 Fujifilm Manufacturing Europe BV Photographic paper and its use in a photo album
GB202006061D0 (en) 2020-04-24 2020-06-10 Fujifilm Mfg Europe Bv Photographic paper

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE642936A (en) * 1963-01-26 1964-07-24
US3170915A (en) * 1960-04-11 1965-02-23 Monsanto Co Sucrose ethers
US3220847A (en) * 1962-02-23 1965-11-30 Eastman Kodak Co Photographic gelatin layers containing the water-soluble salts of various half esters of substituted succinic acid as coating aids
US3300413A (en) * 1963-08-14 1967-01-24 Geoffrey R Ames Surface active compositions containing mixtures of mono- and di-alkyloxymethyl ethers of sugar
US3314936A (en) * 1962-09-10 1967-04-18 Geoffrey R Ames Process for the production of ethers of organic polyhydroxy compounds

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3170915A (en) * 1960-04-11 1965-02-23 Monsanto Co Sucrose ethers
US3220847A (en) * 1962-02-23 1965-11-30 Eastman Kodak Co Photographic gelatin layers containing the water-soluble salts of various half esters of substituted succinic acid as coating aids
US3314936A (en) * 1962-09-10 1967-04-18 Geoffrey R Ames Process for the production of ethers of organic polyhydroxy compounds
BE642936A (en) * 1963-01-26 1964-07-24
US3300413A (en) * 1963-08-14 1967-01-24 Geoffrey R Ames Surface active compositions containing mixtures of mono- and di-alkyloxymethyl ethers of sugar

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
EP0549496A1 (en) * 1991-12-24 1993-06-30 Eastman Kodak Company Glycoside surfactants as coating aids for photographic layers
US5582963A (en) * 1994-10-28 1996-12-10 Fuji Photo Film Co., Ltd. Process for preparation of silver halide photographic material having emulsion layer and antistatic backing layer
US6153034A (en) * 1997-08-03 2000-11-28 Micromod R.P. Ltd Rapid prototyping
US7250202B1 (en) 1998-06-18 2007-07-31 Ilford Imaging Ch Gmbh Recording sheets for ink jet printing
US6071688A (en) * 1998-07-29 2000-06-06 Eastman Kodak Company Providing additives to a coating composition by vaporization

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DE1547823B2 (en) 1975-06-05
DE1547823A1 (en) 1969-11-27
GB1077317A (en) 1967-07-26
BE672440A (en) 1966-03-16

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