WO1991010938A1 - Photographic silver chloride emulsions - Google Patents

Photographic silver chloride emulsions Download PDF

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Publication number
WO1991010938A1
WO1991010938A1 PCT/EP1991/000069 EP9100069W WO9110938A1 WO 1991010938 A1 WO1991010938 A1 WO 1991010938A1 EP 9100069 W EP9100069 W EP 9100069W WO 9110938 A1 WO9110938 A1 WO 9110938A1
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WO
WIPO (PCT)
Prior art keywords
silver chloride
emulsion
coupler
photosensitive
bisphenol derivative
Prior art date
Application number
PCT/EP1991/000069
Other languages
French (fr)
Inventor
Llewellyn James Leyshon
Original Assignee
Kodak Limited
Eastman Kodak Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kodak Limited, Eastman Kodak Company filed Critical Kodak Limited
Priority to EP91901765A priority Critical patent/EP0463136B1/en
Priority to DE69115767T priority patent/DE69115767T2/en
Publication of WO1991010938A1 publication Critical patent/WO1991010938A1/en

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Classifications

    • 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
    • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
    • 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
    • G03C1/035—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein characterised by the crystal form or composition, e.g. mixed grain
    • 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
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • 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
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/3022—Materials with specific emulsion characteristics, e.g. thickness of the layers, silver content, shape of AgX grains
    • 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
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/39212—Carbocyclic
    • G03C7/39216—Carbocyclic with OH groups

Definitions

  • This invention relates to photographic silver chloride emulsions having improved keeping properties.
  • Photographic silver chloride emulsions are now widely used in the manufacture of photographic colour negative paper materials. As such materials age their sensitometric performance changes such that the speed and minimum density (D min ) increase while their contrast decreases.
  • D min speed and minimum density
  • Known techniques for countering these defects in silver halide emulsions in general include the method described in British
  • Specification 1 262 127 which comprises the addition of small quantities of reducing agents such as amino- hexose-reductones. Control of the emulsion pH and pAg can also be beneficial.
  • a photosensitive silver chloride emulsion comprising at least 90% silver chloride whose keeping properties have been improved by the incorporation therein of a bisphenol derivative having two linked phenol rings wherein the hydrogen atom of one of the phenolic hydroxy groups is replaced by a blocking group which is a substituent other than hydrogen and at least one of the phenol rings is substituted.
  • the blocking group may be any group which does not affect the desired properties of the
  • the two phenol rings of the stabilizer may be linked directly by a single bond or indirectly by a linking group.
  • the link between the phenol rings is ortho relative to the phenolic hydroxy group of one ring and the blocked phenolic hydroxy group of the other ring.
  • each phenol ring independently is substituted in a position ortho or para relative to the unblocked or blocked phenolic hydroxy groups. It is further preferred that substituents are present in both ortho and para positions.
  • the bis-phenol compound preferably has the general formula:
  • R is alkyl, cycloalkyl, alkenyl, aryl, acyl, alkylsuphonyl or arylsulphonyl,
  • R 1 is a single bond or a linking group selected from alkylene, alkylidene, a heteroatom or sulphonyl, and
  • each R 2 independently represents one or more substituents each selected from alkyl, alkoxy, alkenyl, cycloalkyl, aryl or aryloxy or, each R independently represents the atoms necessary to complete with the benzene ring to which it is
  • blocking group R are methyl, ethyl, propyl or butyl, cyclohexyl, phenyl, acetyl or benzoyl.
  • linking group R 1 examples are methylene, butylidene, 3,5,5,-trimethylhexylidene, oxygen, sulphur or sulphonyl.
  • An especially preferred group of bis-phenol compounds has the general formula:
  • R 1 and R are as defined above, and
  • R 3 , R 4 , R 5 and R 6 are each
  • R 3 and R 4 are identical and R 5 and R 6 are identical.
  • the blocked bisphenol derivatives are readily prepared from their unblocked counterparts, many of which are commercially available.
  • a blocking group may be introduced into the unblocked parent bisphenol by reaction with an appropriate reactive halogen-containing compound e.g. an alkyl bromide, acyl chloride, sulphonyl chloride or a dialkyl sulphate e.g. diethyl sulphate.
  • unblocked parent bisphenols from which the stabilizers of the present invention may be prepared are as follows:
  • the present invention also provides a method for improving the keeping properties of a silver chloride emulsion comprising the incorporation therein of a bisphenol derivative having two linked phenol rings wherein the hydrogen atom of one of the phenolic hydroxy groups is .replaced by a blocking group which is a substituent other than hydrogen and at least one of the phenol rings is substituted.
  • the present invention further provides a photographic material comprising a support bearing a layer of a photosensitive silver chloride emulsion said material having incorporated therein a bisphenol derivative having two linked phenol rings wherein the hydrogen atom of one of the phenolic hydroxy groups is replaced by a blocking group which is a substituent other than hydrogen and at least one of the phenol rings is substituted in order to improve its keeping properties.
  • the silver chloride emulsions used in the present invention contain more than 90 mole %, silver chloride preferably the emulsions are substantially pure silver chloride.
  • the bis-phenol compounds may be incorporated in the silver chloride emulsions as a dispersion of droplets of a high boiling coupler solvent containing the bis-phenol. Such droplets may also contain a colour coupler. Alternatively they may be
  • the colour coupler may be of any class of couplers useful in colour photographic materials.
  • coupler classes include phenolic and naphtholic cyan couplers, pyrazolidone and
  • Such couplers preferably have the general formula:
  • R 7 represents one or more substituents of
  • R 8 is a coupliig-off group, preferably an aryloxy group.
  • the fourth dispersion contained a comparison material the bis-phosphate ester of the formula:
  • Dispersions of each coupler alone were also made.
  • the coupler was dissolved in its own weight of ethyl acetate and one half its weight of dibutyl phthalate. When present the bisphenol was included at half the weight of the coupler.
  • the oil solutions were dispersed in aqueous gelatin using ultrasonic agitation as in Example 1.
  • Coupler (B) Each dispersion containing Coupler (B) was mixed with a red-sensitised silver chloride emulsion and coated on a resin-coated paper support, such that the silver and coupler coverages were, respectively,
  • coatings was made from the dispersions at the same component coverages but utilising a blue-sensitised emulsion (as used in Example 1) in place of the red sensitised emulsion.
  • Coupler (C) was coated together with a green sensitised silver
  • chloride emulsion at silver and coupler coverages of 285 mg/m2 and 447 mg/m2 respectively.
  • Sample strips of the fresh coatings were exposed and processed through RA4 chemistry to assess sensitometric performance. Another strip from each coating was incubated in the dark for 8 days at 50°C and 50% RH before being exposed and processed.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A photosensitive silver chloride emulsion comprising at least 90 % silver chloride whose keeping properties have been improved by the incorporation therein of a bisphenol derivative having two linked phenol rings wherein the hydrogen atom of one of the phenolic hydroxy groups is replaced by a blocking group which is a substituent other than hydrogen and at least one of the phenol rings is substituted.

Description

PHOTOGRAPHIC SILVER CHLORIDE EMULSIONS
This invention relates to photographic silver chloride emulsions having improved keeping properties.
Photographic silver chloride emulsions are now widely used in the manufacture of photographic colour negative paper materials. As such materials age their sensitometric performance changes such that the speed and minimum density (Dmin) increase while their contrast decreases. Known techniques for countering these defects in silver halide emulsions in general include the method described in British
Specification 1 262 127 which comprises the addition of small quantities of reducing agents such as amino- hexose-reductones. Control of the emulsion pH and pAg can also be beneficial.
There is, however, a need to improve the keeping properties (shelf life) of silver chloride emulsions still further.
Blocked bis-phenols have been described as photographic dye image stabilisers in European Patent specification 0 246 766 (US Patent 4 782 011).
Specifically the compounds were incorporated into silver chlorobromide emulsions.
According to the present invention there is provided a photosensitive silver chloride emulsion comprising at least 90% silver chloride whose keeping properties have been improved by the incorporation therein of a bisphenol derivative having two linked phenol rings wherein the hydrogen atom of one of the phenolic hydroxy groups is replaced by a blocking group which is a substituent other than hydrogen and at least one of the phenol rings is substituted.
The blocking group may be any group which does not affect the desired properties of the
stabilizer. The two phenol rings of the stabilizer may be linked directly by a single bond or indirectly by a linking group. Preferably, the link between the phenol rings is ortho relative to the phenolic hydroxy group of one ring and the blocked phenolic hydroxy group of the other ring.
Preferably, each phenol ring independently is substituted in a position ortho or para relative to the unblocked or blocked phenolic hydroxy groups. It is further preferred that substituents are present in both ortho and para positions.
The bis-phenol compound preferably has the general formula:
'
Figure imgf000004_0001
wherein
R is alkyl, cycloalkyl, alkenyl, aryl, acyl, alkylsuphonyl or arylsulphonyl,
R1 is a single bond or a linking group selected from alkylene, alkylidene, a heteroatom or sulphonyl, and
each R2 independently represents one or more substituents each selected from alkyl, alkoxy, alkenyl, cycloalkyl, aryl or aryloxy or, each R independently represents the atoms necessary to complete with the benzene ring to which it is
attached, a fused polycyclic aromatic ring structure.
all of said alkyl, alkoxy, cycloalkyl, alkylene, alkenyl, aryl, aryloxy and acyl groups being optionally substituted. Examples of blocking group R are methyl, ethyl, propyl or butyl, cyclohexyl, phenyl, acetyl or benzoyl.
Examples of linking group R1 are methylene, butylidene, 3,5,5,-trimethylhexylidene, oxygen, sulphur or sulphonyl.
An especially preferred group of bis-phenol compounds has the general formula:
Figure imgf000005_0001
R R wherein R1 and R are as defined above, and
R3, R4, R5 and R6 are each
independently a substituted or unsubstituted alkyl, alkenyl, cycloalkyl or aryl group. Preferably, R3 and R4 are identical and R5 and R6 are identical.
Specific examples of bis-phenols suitable for use in the present invention are as follows:
Figure imgf000005_0002
Figure imgf000006_0001
Figure imgf000007_0001
Figure imgf000008_0001
Figure imgf000009_0001
The blocked bisphenol derivatives are readily prepared from their unblocked counterparts, many of which are commercially available. For example, a blocking group may be introduced into the unblocked parent bisphenol by reaction with an appropriate reactive halogen-containing compound e.g. an alkyl bromide, acyl chloride, sulphonyl chloride or a dialkyl sulphate e.g. diethyl sulphate.
Examples of unblocked parent bisphenols from which the stabilizers of the present invention may be prepared are as follows:
4
Figure imgf000010_0001
Figure imgf000011_0001
The present invention also provides a method for improving the keeping properties of a silver chloride emulsion comprising the incorporation therein of a bisphenol derivative having two linked phenol rings wherein the hydrogen atom of one of the phenolic hydroxy groups is .replaced by a blocking group which is a substituent other than hydrogen and at least one of the phenol rings is substituted.
The present invention further provides a photographic material comprising a support bearing a layer of a photosensitive silver chloride emulsion said material having incorporated therein a bisphenol derivative having two linked phenol rings wherein the hydrogen atom of one of the phenolic hydroxy groups is replaced by a blocking group which is a substituent other than hydrogen and at least one of the phenol rings is substituted in order to improve its keeping properties.
The silver chloride emulsions used in the present invention contain more than 90 mole %, silver chloride preferably the emulsions are substantially pure silver chloride.
The bis-phenol compounds may be incorporated in the silver chloride emulsions as a dispersion of droplets of a high boiling coupler solvent containing the bis-phenol. Such droplets may also contain a colour coupler. Alternatively they may be
incorporated as solutions in an alcohol, for example, methanol. The colour coupler may be of any class of couplers useful in colour photographic materials.
Examples of such coupler classes include phenolic and naphtholic cyan couplers, pyrazolidone and
pyrazolotriazole magenta couplers and acylacetanilide yellow couplers.
Particularly good results are obtained with the pivaloylacetanilide couplers and especially those with aryloxy coupling-off groups. Such couplers preferably have the general formula:
Figure imgf000012_0001
wherein R7 represents one or more substituents of
the type found in such couplers, and R8 is a coupliig-off group, preferably an aryloxy group.
Suitable emulsions, emulsion additives and couplers for use in the emulsions and elements of this invention are described in Research Disclosure,
December 1978, Item 17643, published by Kenneth Mason Publications Ltd., 12a North Street, Emsworth, Hants PO10 7DQ, U.K. In particular, information on couplers and on methods for their dispersions are given in Sections VII and XIV, respectively, of this article.
The following examples are included for a better understanding of the invention.
EXAMPLE 1
Four separate dispersions of the following coupler were prepared:
Figure imgf000013_0001
OH
dissolved in one quarter its weight of dibutyl
phthalate and 2-(2-butoxyethoxy)ethyl acetate. Two of the dispersions also contained a blocked bis-phenol as indicated below at concentrations equal to half that of the coupler, by weight. The fourth dispersion contained a comparison material the bis-phosphate ester of the formula:
(PhO)2PO.O(CH2)10O.PO(OPh)2 at the same concentration.
Each dispersion was mixed with a
blue-sensitive silver chloride emulsion and coated on a resin-coated paper support, such that the silver and coupler coverages were, respectively, 0.18 g/m and
0.40 g/m2
Strips of the fresh coatings sere exposed and processed through RA4 chemistry to assess
sensitometric performance. Further strips were
incubated in the dark for 1 week at 50 °C and 50% RH before being similarly exposed and processed. The Table below shows figures for the Dmin and contrast of the freshly coated and incubated strips from each coating. The columns labelled "Δ" show the difference between the fresh and incubated samples. Taking the coating without any addendum as a reference, the two blocked bis-phenols reduced the extent of Dmin increase and the loss in contrast due to incubation. A contrary effect was show by the comparison bis-phosphate ester.
Figure imgf000014_0002
EXAMPLE 2
Dispersions were prepared containing Compound I-11 with the colour couplers below:
Figure imgf000014_0001
Figure imgf000015_0001
Dispersions of each coupler alone were also made. In each dispersion the coupler was dissolved in its own weight of ethyl acetate and one half its weight of dibutyl phthalate. When present the bisphenol was included at half the weight of the coupler. The oil solutions were dispersed in aqueous gelatin using ultrasonic agitation as in Example 1.
Each dispersion containing Coupler (B) was mixed with a red-sensitised silver chloride emulsion and coated on a resin-coated paper support, such that the silver and coupler coverages were, respectively,
239 mg/m 2 and 425 mg/m2. A second pair of
coatings was made from the dispersions at the same component coverages but utilising a blue-sensitised emulsion (as used in Example 1) in place of the red sensitised emulsion.
Similarly the dispersions of Coupler (C) were coated together with a green sensitised silver
chloride emulsion at silver and coupler coverages of 285 mg/m2 and 447 mg/m2 respectively.
Sample strips of the fresh coatings were exposed and processed through RA4 chemistry to assess sensitometric performance. Another strip from each coating was incubated in the dark for 8 days at 50°C and 50% RH before being exposed and processed.
The following table shows figures for the Dmin of the freshly coated and incubated strips. The column labelled "Δ" highlights the dif ferences between the two sets, associated with the incubation treatment. All the coatings show an increase in
Dmin on incubation and the magnitude of this
increase is always reduced by the presence of the bisphenol.
The beneficial effect of the invention is thus shown not to be dependent on the colour
sensitiviy of the emulsion or the coupler it contains.
Figure imgf000016_0001

Claims

1. A photosensitive silver chloride emulsion comprising at least 90% silver chloride whose keeping properties have been improved by the incorporation therein of a bisphenol derivative having two linked phenol rings wherein the hydrogen atom of one of the phenolic hydroxy groups is replaced by a blocking group which is a substituent other than hydrogen and at least one of the phenol rings is substituted.
2. A photosensitive emulsion as claimed in claim 1 in which the bisphenol derivative has the general formula:
Figure imgf000017_0001
wherein
R is alkyl, cycloalkyl, alkenyl, aryl, acyl, alkylsuphonyl or arylsulphonyl,
R1 is a single bond or a linking group selected from alkylene, alkylidene, a heteroatom or sulphonyl, and
each R2 independently represents one or more substituents each selected from alkyl, alkoxy, alkenyl, cycloalkyl, aryl or aryloxy or, each R independently represents the atoms necessary to complete with the benzene ring to which it is
attached, a fused polycyclic aromatic ring structure.
3. A photosensitive emulsion as claimed in claim 1 or 2 in which the bisphenol derivative has the general formula:
Figure imgf000018_0001
wherein R1 and R are as defined above, and
R3, R4, R5 and R6 are each
independently a substituted or unsubstituted alkyl, alkenyl, cycloalkyl or aryl group.
4. A photosensitive emulsion as claimed in claim 3 in which R3 and R4 are identical and R5 and R6 are identical.
5. A photosensitive emulsion as claimed in any of claims 1-4 which comprises. substantially pure silver chloride.
6. A photosensitive emulsion as claimed in any of claims 1-5 which further comprises a colour coupler.
7. A photosensitive emulsion as claimed in claim 6 in which the coupler is a yellow, cyan or magenta dye-forming coupler.
8. A photosensitive emulsion as claimed in claim 6 in which the coupler is an acylacetanilide, phenolic, naphtholic, pyrazolone or pyrazoloazole coupler.
9. A method for improving the keeping properties of a silver chloride emulsion comprising at least 90% silver chloride which comprises
incorporating therein a bisphenol derivative as defined in any of claims 1-4.
10. A photographic material comprising a support bearing a layer of a photosensitive silver chloride emulsion comprising at least 90% silver chloride said material having incorporated therein a bisphenol derivative as defined in any of claims 1-4 in order to improve its keeping properties.
PCT/EP1991/000069 1990-01-17 1991-01-12 Photographic silver chloride emulsions WO1991010938A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP91901765A EP0463136B1 (en) 1990-01-17 1991-01-12 Photographic silver chloride emulsions
DE69115767T DE69115767T2 (en) 1990-01-17 1991-01-12 PHOTOGRAPHIC SILVER CHLORIDE EMULSIONS

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9001078.6 1990-01-17
GB909001078A GB9001078D0 (en) 1990-01-17 1990-01-17 Photographic silver chloride emulsions

Publications (1)

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WO1991010938A1 true WO1991010938A1 (en) 1991-07-25

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EP (1) EP0463136B1 (en)
JP (1) JPH04506579A (en)
DE (1) DE69115767T2 (en)
GB (1) GB9001078D0 (en)
WO (1) WO1991010938A1 (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1313964C (en) * 1988-03-30 1993-03-02 Merle W. North Apparatus for forming a web
GB8927563D0 (en) * 1989-12-06 1990-02-07 Kodak Ltd Photographic silver halide materials

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 112, no. 4, 22 January 1990 Columbus, Ohio, USA S.Hirabayashi: "Silver halide color photographic material containing a magenta coupler of pyrazoloazole type and a bisphenol derivative to improve color quality" page 491; left-hand column; ref. no. 28056C see abstract *

Also Published As

Publication number Publication date
DE69115767T2 (en) 1997-02-06
EP0463136A1 (en) 1992-01-02
EP0463136B1 (en) 1995-12-27
GB9001078D0 (en) 1990-03-14
DE69115767D1 (en) 1996-02-08
JPH04506579A (en) 1992-11-12

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