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US3545974A - Method for preparing photographic light-sensitive elements - Google Patents

Method for preparing photographic light-sensitive elements Download PDF

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Publication number
US3545974A
US3545974A US714020A US3545974DA US3545974A US 3545974 A US3545974 A US 3545974A US 714020 A US714020 A US 714020A US 3545974D A US3545974D A US 3545974DA US 3545974 A US3545974 A US 3545974A
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Prior art keywords
surface active
compound
active agent
photographic
photographic light
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US714020A
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Fumihiko Nishio
Masakazu Yoneyama
Minoru Yamada
Kameji Nagao
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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
    • G03C1/38—Dispersants; Agents facilitating spreading

Definitions

  • the present invention relates generally to a method for preparing light-sensitive elements and more particua surface active agent thus incorporated does not reduce the photographic properties of the photographic light-sensitive element not reduce the speed of forming the color images on developing the photographic light-sensitive element.
  • R-I- R'o rr 011260 wherein R represents an alkyl group having more than 6 carbon atoms, R represents ethylene or propylene, and p+q is a positive integer larger than 5, excellent for improving the coating properties of the coating composition, is inadequate for color photography since it diminishes the clarity of the colors and it accelerates the fading of the color image due to heat and moisture exposure thereby reducing the life or stability of the color photograph. It is believed that the deleterious results are caused by the bleaching or silver-removing power of the surface active agent by oxidation during the developing process.
  • an aqueous emulsified dispersion of the coupler is prepared with an oily material and an anionic surface active agent which is added to the photographic silver halide emulsion.
  • an anionic surface active agent shown by the general Formula A mentioned above is incorporated into the photographic silver halide emulsion, the
  • colloidal stability of the dispersed coupler is reduced, causing aggregation of the coupler during developing and reduction in transparency of the emulsion layers after developing.
  • an object of the present invention is to provide an amphoteric surface active agent in a photographic coating composition for improving the coating properties thereof without the aforesaid disadvantages.
  • Another object of this invention is to provide a method for preparing a photographic light-sensitive element, in particular, a color photographic light-sensitive element, by employing the aforesaid amphoteric surface active agent for improving the coating property of the photographic coating composition without reducing either the photographic properties of the light-sensitive element or the fastness of the color images.
  • the synthesis (i) mentioned above may be conducted by the method described in Kogyo Kagaku Zasshi (Journal of Industrial Chemistry); vol. 63, 595-600 (1960), and the synthesis (ii) may be conducted by the method described in Kogyo Kagaku Zasshi; vol. 60, 909 (1957).
  • the compound represented by the aforesaid general Formula B may be incorporated in any coating composition of a photographic light-sensitive element but is more suitably incorporated into a photographic silver halide emulsion. It is particularly suitable for photographic silver halide emulsions in which the second ripening has been finished immediately before coating. Furthermore, the novel surface active agent of this invention, if desired, may be used together with other conventional surface active agents.
  • amphoteric surface active agent is varied in accordance with various conditions, such as the type of coating composition, the manner of coating and the like, but in general the addition of 0.01- 0.2% by weight of the surface active agent based on the weight of the coating composition gives the best effect. This amount corresponds to 0.1-2.0 g. per one kg. of gelatin in the coating composition.
  • a photographic emulsion containing the aforesaid surface active agent can be uniformly applied to a support with a high speed without deleterious effect on the photographic properties of the light-sensitive element.
  • color images having good fastness can be obtained after developing the color photographic light-sensitive element containing the surface active agent of this invention.
  • amphoteric surface active agent used in this invention causes few undesirable reactions with other additives of the emulsion, difficulties otherwise encountered during production of photographic light-sensitive elements are reduced.
  • Example 1 An emulsifier dispersion prepared by dispersing a solution of 2.3 g. of a cyan coupler having the following in 5.0 ml. of tri-ortho-cresylphosphate ester in 40 ml. of an aqueous gelatin solution containing 0.2 g. of sodium n-dodecylbenzene sulfinate was added to 100 g. of a red-sensitive photographic emulsion containing 7 g. of gelatin and 5 g. of silver chlorobromide.
  • the colored samples thus obtained were subjected to the following fading tests: (A) the sample was maintained for days under the conditions of 60 C. and 75% relative humidity; and (B) the sample was maintained for four hours at 120 C.
  • the results are shown in the following table in which the initial optical density of the cyancolored image was 2.0.
  • Example 2 Into a red-sensitive emulsion containing the coupler as shown in Example 1 were added 2.0 ml. of a 1% solution of each of Compounds I, II, III, and V, and 2.0 ml. of a 1% solution of a surface active agent having the following formula The coating composition thus prepared was applied to a triacetyl cellulose film at C. and set at 5 C. To the thus coated wet emulsion layer a coating composition prepared by adding 2 ml. of a 1% solution of a surface active agent, n-dodecylbenzene sulfonate, to 100 g. of a 2% gelatin solution was applied with various coating speeds.
  • a coating composition prepared by adding 2 ml. of a 1% solution of a surface active agent, n-dodecylbenzene sulfonate, to 100 g. of a 2% gelatin solution was applied with various coating speeds.
  • the colloidal stability of the coupler-containing the emulsified dispersion was signifivantly better than the conventional compound V. Further, the emulsion layer formed by the present invention has good transparency.
  • Example 4 An emulsified dispersion prepared by dispersing a solution of 2.0 g. of a yellow coupler having the formula:
  • Each of the emulsion samples thus prepared was mixed with 5 ml. of a 1% solution of compound I, II or V and 3 ml. of a 3% acetate solution of triethylene phosphorous amide, and the mixture was applied to a triacetyl cellulose film followed by drying to provide a light-sensitive film.
  • the light-sensitive film was then blue-exposed stepwise and processed as in Example 1 to provide a yellow image.
  • the blue density D and red density D of the image were measured, the results of which are shown in the following table.
  • the blue density D shows the relative strength of yellow coupling and the red density D shows the relative density of a silver image remaining after processing.
  • a photographic coating composition comprising a gelatin containing silver halide emulsion and a minor amount of a surface active agent having the formula:
  • tive agent is present in an amount of 0.0 10.2% by weight based on the weight of the coating composition.
  • composition of claim 1 wherein said silver halide is silver ehlorobromide.
  • composition of claim 1 wherein said silver halide is silver iodobromide.
  • composition of claim 7 wherein said coupling agent is a cyan coupler having the formula:
  • a photographic element comprising a support having applied thereto a photographic coating compositioncomprising a gelatin containing silver halide emulsion and a minor amount of a surface active agent having the formula:
  • R is an alkyl group having 8-20 carbon atoms and p and q of each represent positive integers.

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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)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

United States Patent Oflice 3,545,974 Patented Dec. 8, 1970 3,545,974 METHOD FOR PREPARING PHOTOGRAPHIC LIGHT-SENSITIVE ELEMENTS Fumihiko Nishio, Masakazu Yoneyama, Minoru Yamada, and Kameji Nagao, Kanagawa, Japan, assignors to Fuji Shashin Film Kabushiki Kaisha, Kanagawa, Japan No Drawing. Filed Mar. 18, 1968, Ser. No. 714,020 Claims priority, application Japan, Mar. 17, 1967, 42/16,790 Int. Cl. G03c 1/04 US. Cl. 96-1145 16 Claims ABSTRACT OF THE DISCLOSURE A method and product resulting therefrom for incorporating a wetting agent into a silver halide emulsion, said wetting agent having the general formula:
omorno rr noorrzonornfiqomomom-r on ornooowhereby the coating properties of said emulsion is improved without reducing the fastness of the color images produced on developing.
BACKGROUND OF THE INVENTION The present invention relates generally to a method for preparing light-sensitive elements and more particua surface active agent thus incorporated does not reduce the photographic properties of the photographic light-sensitive element not reduce the speed of forming the color images on developing the photographic light-sensitive element.
Conventional surface active agents have not satisfactorily met the above-mentioned requirements. For example, an amphoteric surface agent represented by the Formula A:
R-I- R'o rr 011260 wherein R represents an alkyl group having more than 6 carbon atoms, R represents ethylene or propylene, and p+q is a positive integer larger than 5, excellent for improving the coating properties of the coating composition, is inadequate for color photography since it diminishes the clarity of the colors and it accelerates the fading of the color image due to heat and moisture exposure thereby reducing the life or stability of the color photograph. It is believed that the deleterious results are caused by the bleaching or silver-removing power of the surface active agent by oxidation during the developing process.
When producing a color photographic light-sensitive element using a hydrophobic oil-dispersion type coupler, an aqueous emulsified dispersion of the coupler is prepared with an oily material and an anionic surface active agent which is added to the photographic silver halide emulsion. However, when the surface active agent shown by the general Formula A mentioned above is incorporated into the photographic silver halide emulsion, the
colloidal stability of the dispersed coupler is reduced, causing aggregation of the coupler during developing and reduction in transparency of the emulsion layers after developing.
SUMMARY OF THE INVENTION Thus, an object of the present invention is to provide an amphoteric surface active agent in a photographic coating composition for improving the coating properties thereof without the aforesaid disadvantages.
Another object of this invention is to provide a method for preparing a photographic light-sensitive element, in particular, a color photographic light-sensitive element, by employing the aforesaid amphoteric surface active agent for improving the coating property of the photographic coating composition without reducing either the photographic properties of the light-sensitive element or the fastness of the color images.
According to the present invention, in the production of a photographic light-sensitive element, an amphoteric surface active agent represented by the general Formula B:
(CH2C H2O) H C112?HCHzN-(CHzCHzOLJT OH CHrC 00 (B) wherein R represents an alkyl group having 820 carbon atoms and p and q each represent positive integers, is incorporated in a coating composition for the light-sensitive element.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT The practical examples of the surface active agent used in this invention are shown below:
R p+q Compound I (3121125 2 (P=q) Compound II CuHzu 2 (P=t1) Compound III 014 5 Compound IV 0141120 30 These compounds may be prepared by the following methods:
The synthesis (i) mentioned above may be conducted by the method described in Kogyo Kagaku Zasshi (Journal of Industrial Chemistry); vol. 63, 595-600 (1960), and the synthesis (ii) may be conducted by the method described in Kogyo Kagaku Zasshi; vol. 60, 909 (1957).
The compound represented by the aforesaid general Formula B may be incorporated in any coating composition of a photographic light-sensitive element but is more suitably incorporated into a photographic silver halide emulsion. It is particularly suitable for photographic silver halide emulsions in which the second ripening has been finished immediately before coating. Furthermore, the novel surface active agent of this invention, if desired, may be used together with other conventional surface active agents.
The optimum amount of the amphoteric surface active agent is varied in accordance with various conditions, such as the type of coating composition, the manner of coating and the like, but in general the addition of 0.01- 0.2% by weight of the surface active agent based on the weight of the coating composition gives the best effect. This amount corresponds to 0.1-2.0 g. per one kg. of gelatin in the coating composition.
According to the process of this invention, a photographic emulsion containing the aforesaid surface active agent can be uniformly applied to a support with a high speed without deleterious effect on the photographic properties of the light-sensitive element. In particular, after developing the color photographic light-sensitive element containing the surface active agent of this invention, color images having good fastness can be obtained.
Furthermore, since the amphoteric surface active agent used in this invention causes few undesirable reactions with other additives of the emulsion, difficulties otherwise encountered during production of photographic light-sensitive elements are reduced.
The invention will now be explained in detail by reference to the following examples, in which compounds I-IV are the surface active agents of the present invention, while compound V stands for a conventional suface active agent shown by the aforesaid general Formula A in which R is C H2g, R is C H and p+q is 5.
Example 1 An emulsifier dispersion prepared by dispersing a solution of 2.3 g. of a cyan coupler having the following in 5.0 ml. of tri-ortho-cresylphosphate ester in 40 ml. of an aqueous gelatin solution containing 0.2 g. of sodium n-dodecylbenzene sulfinate was added to 100 g. of a red-sensitive photographic emulsion containing 7 g. of gelatin and 5 g. of silver chlorobromide.
Into each of such emulsions were added 5 ml. of a 1% solution of compound I, II, III, IV or V and 3 ml. of a 3% acetone solution of triethylene phosphorous amide as a hardening agent, and the coating composition thus prepared was applied to a triacetyl cellulose support followed by drying to provide a light-sensitive film. The light-sensitive film was red-exposed stepwise, developed in a color developer containing 4-amino-3-methyl-N, N- dimethylaniline hydrochloride as a developing agent and then subjected to subsequent processings, such as, bleaching, fixing, water-washing and drying, as in any conventional manner, to provide a colored sample. The colored samples thus obtained were subjected to the following fading tests: (A) the sample was maintained for days under the conditions of 60 C. and 75% relative humidity; and (B) the sample was maintained for four hours at 120 C. The results are shown in the following table in which the initial optical density of the cyancolored image was 2.0.
From the results, it was confirmed that by the incorporation of the conventional surface active agent V, the fading of the colored image was accelerated remarkably but no such marked acceleration of fading was observed in the case of incorporating the surface active agents 1, II, III and IV of this invention. Also, by the addition of the surface active agent of this invention, fastness of the colored image similar to or higher than that of the control sample, in which no surface active agent was added, was obtained.
Example 2 Into a red-sensitive emulsion containing the coupler as shown in Example 1 were added 2.0 ml. of a 1% solution of each of Compounds I, II, III, and V, and 2.0 ml. of a 1% solution of a surface active agent having the following formula The coating composition thus prepared was applied to a triacetyl cellulose film at C. and set at 5 C. To the thus coated wet emulsion layer a coating composition prepared by adding 2 ml. of a 1% solution of a surface active agent, n-dodecylbenzene sulfonate, to 100 g. of a 2% gelatin solution was applied with various coating speeds. When the coating speed was increased over a definite speed, it became impossible to spread the second coating composition on the surface of the first emulsion layer. However, the upper limit of the coating speed was remarkably improved by adding compound I, II or III of this invention to the second coating composition, as shown in the following table.
Surfactant: Limit of coating speed (m./ min.) None (control) 9 Compound I Compound 11 Compound III 50 Compound V (comparative) 42 Example 3 Turbidity (relative value) Amount,
Surfactant 1n 0 6 hrs. 12 hrs.
None (eontrol). 8. 2 8. 6 9. 6 Compound II. 5 10.2 10.2 13. 0 D0 10 10.2 11.7 13.7 Compound IV 5 8.0 J. 2 12. 0 o 10 17.9 18. 3 18. 0 Compound V... 5 11.2 12. 8 14. 1 0 10 20. 1 21. 5 24, 6
As is clear from the above results, by the addition of compounds II and IV of this invention, the colloidal stability of the coupler-containing the emulsified dispersion was signifivantly better than the conventional compound V. Further, the emulsion layer formed by the present invention has good transparency.
Example 4 An emulsified dispersion prepared by dispersing a solution of 2.0 g. of a yellow coupler having the formula:
(1100C 12IIz5(n) l OCllr in a 2.0 ml. of di-n-butylphthalic acid ester in 30 ml. of an aqueous 10% gelatin solution containing 0.2 g. of sodium n-dodecylbenzene sulfonate was added to 100 g. of a red-sensitive photographic emulsion containing 6 g. of gelatin and 6 g. of silver iodobromide.
Each of the emulsion samples thus prepared was mixed with 5 ml. of a 1% solution of compound I, II or V and 3 ml. of a 3% acetate solution of triethylene phosphorous amide, and the mixture was applied to a triacetyl cellulose film followed by drying to provide a light-sensitive film. The light-sensitive film was then blue-exposed stepwise and processed as in Example 1 to provide a yellow image. The blue density D and red density D of the image were measured, the results of which are shown in the following table. The blue density D shows the relative strength of yellow coupling and the red density D shows the relative density of a silver image remaining after processing.
Surfactant Db D,
Compound I..- 2. 0.07 Compound II 2. O 0. 05 Compound V 2. 0 0.35
As shown in the results,.when using compounds I and II of this invention, the silver image was removed effectively by bleaching and clear yellow dye images were obtained whereas when using the conventional compound V, silver images remained to a considerable extent.
What is claimed is:
1. A photographic coating composition comprising a gelatin containing silver halide emulsion and a minor amount of a surface active agent having the formula:
tive agent is present in an amount of 0.0 10.2% by weight based on the weight of the coating composition.
7. The composition of claim 1 wherein said silver halide emulsion contains a suitable coupling agent.
8. The composition of claim 1 wherein said silver halide is silver ehlorobromide.
9. The composition of claim 1 wherein said silver halide is silver iodobromide.
10. The composition of claim 7 wherein said coupling agent is a cyan coupler having the formula:
Cl NHCOOH2O CHa\ C5H11 C5Hn 11. A photographic element comprising a support having applied thereto a photographic coating compositioncomprising a gelatin containing silver halide emulsion and a minor amount of a surface active agent having the formula:
/(CH2CH20) pH noomonomfiqomomm 11 0H onto 0 0- wherein R is an alkyl group having 8-20 carbon atoms and p and q of each represent positive integers.
12. The element as claimed in claim 11 wherein R is C H and p+q is 2.
13. The element as claimed in claim 11 wherein R is C H and p-l-q is 2.
14. The element as claimed in claim 11 wherein R is C H and p+q is 5.
15. The element as claimed in claim 11 wherein R is C H and p+q is 30.
16. The element as claimed in claim 11 wherein the amount of said compound is 0.010.2% by weight of the coating composition.
References Cited UNITED STATES PATENTS 3,441,413 4/1969 Nishio et a1 96114.5
NORMAN G. TORCHIN, Primary Examiner J. R. HIGHTOWER, Assistant Examiner
US714020A 1967-03-17 1968-03-18 Method for preparing photographic light-sensitive elements Expired - Lifetime US3545974A (en)

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GB (1) GB1164095A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
US5155007A (en) * 1990-03-30 1992-10-13 Konica Corporation Silver halide photographic material
US6071688A (en) * 1998-07-29 2000-06-06 Eastman Kodak Company Providing additives to a coating composition by vaporization
US7250202B1 (en) 1998-06-18 2007-07-31 Ilford Imaging Ch Gmbh Recording sheets for ink jet printing
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

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2140572B (en) * 1983-05-26 1986-06-18 Kodak Ltd Photographic dispersions
US5158863A (en) * 1989-01-17 1992-10-27 Eastman Kodak Company Methods of forming stable dispersions of photographic materials
US4990431A (en) * 1989-01-17 1991-02-05 Eastman Kodak Company Methods of forming stable dispersions of photographic materials
IT1232339B (en) * 1989-09-25 1992-01-28 Minnesota Mining & Mfg MULTI-LAYER PHOTOGRAPHIC ELEMENTS HAVING IMPROVED OUTDOOR QUALITY.

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3441413A (en) * 1964-07-07 1969-04-29 Fuji Photo Film Co Ltd Photographic elements having gelatinous coating compositions containing amphoteric surface active agents

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3441413A (en) * 1964-07-07 1969-04-29 Fuji Photo Film Co Ltd Photographic elements having gelatinous coating compositions containing amphoteric surface active agents

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
US5155007A (en) * 1990-03-30 1992-10-13 Konica Corporation Silver halide photographic material
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
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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FR1557345A (en) 1969-02-14
DE1622934C3 (en) 1974-02-07
GB1164095A (en) 1969-09-10
DE1622934B2 (en) 1973-07-19
DE1622934A1 (en) 1971-11-18
BE712297A (en) 1968-07-15

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