EP0073636B2 - Photographic elements containing ballasted couplers - Google Patents

Photographic elements containing ballasted couplers Download PDF

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Publication number
EP0073636B2
EP0073636B2 EP19820304461 EP82304461A EP0073636B2 EP 0073636 B2 EP0073636 B2 EP 0073636B2 EP 19820304461 EP19820304461 EP 19820304461 EP 82304461 A EP82304461 A EP 82304461A EP 0073636 B2 EP0073636 B2 EP 0073636B2
Authority
EP
European Patent Office
Prior art keywords
group
coupler
coupling
couplers
dye
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
EP19820304461
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German (de)
English (en)
French (fr)
Other versions
EP0073636A1 (en
EP0073636B1 (en
Inventor
Gregory James Lestina
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
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Eastman Kodak Co
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Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of EP0073636A1 publication Critical patent/EP0073636A1/en
Publication of EP0073636B1 publication Critical patent/EP0073636B1/en
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Publication of EP0073636B2 publication Critical patent/EP0073636B2/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
    • 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
    • G03C7/32—Colour coupling substances
    • G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific

Definitions

  • This invention relates to photographic elements containing ballasted couplers.
  • Images are commonly obtained in the photographic art by a coupling reaction between the development product of a silver halide developing agent (i.e., oxidized aromatic primary amino developing agent) and a color forming compound commonly referred to as a coupler.
  • the dyes produced by coupling are indoaniline, azomethine, indamine or indophenol dyes, depending upon the chemical composition of the coupler and the developing agent.
  • the subtractive process of color formation is ordinarily employed in multicolor photographic elements and the resulting image dyes are usually cyan, magenta and yellow dyes which are formed in or adjacent silver halide layers sensitive to radiation complementary to the radiation absorbed by the image dye; i.e., silver halide emulsions sensitive to red, green and blue radiation.
  • couplers which form cyan dyes upon reaction with oxidized color developing agents are phenols and naphthols.
  • Representative couplers are described in the following patents and publications: U.S. Patents 2,772,162; 2,895,826; 3,002,836; 3,034,892; 2,474,293; 2,423,730; 2,367,531; 3,041,236 and "Farbkuppler-ein Literaturubersicht", published in Agfa Mitannonen, Band II, pp. 156-175 (1961).
  • Preferred couplers which form magenta dyes upon reaction with oxidized color developing agent are pyrazolones, pyrazolotriazoles, pyrazolobenzimidazoles and indazolones.
  • Representative couplers are described in such patents and publications as U.S. Patents 2,600,788; 2,369,489; 2,343,703; 2,311,082; 2,673,801; 3,152,896; 3,519,429; 3,061,432; 3,062,653; 3,725,067; 2,908,573 and "Farbkuppler-eine Literaturubersicht", published in Agfa Mitannonen, Band II, pp. 126-156 (1961).
  • Couplers which form yellow dyes upon reaction with oxidized color developing agent are acylacetanilides such as benzoylacetanilides and pivalylacetanilides.
  • Representative couplers are described in the following patents and publications: U.S. Patents 2,875,057; 2,407,210; 3,265,506; 2,298,443; 3,048,194; 3,447,928 and "Farbkuppler-eine Literaturubersicht", published in Agfa Mitannonen, Band II, pp. 112-126 (1961).
  • Couplers which form black or neutral dyes upon reaction with oxidized color developing agent.
  • Representative couplers are resorcinols and m-aminophenols such as are described in U.S. Patents 1,939,231; 2,181,944; 2,333,106; 4,126,461; German OLS 2,644,194 and German OLS 2,650,764.
  • Couplers Also known are compounds which react with oxidized color developing agent in the same way as couplers but which do not yield a dye. Such compounds are employed to modify the photographic image by competing with dye-forming coupler for oxidized color developing agent or by releasing a photographic reagent, such as a development inhibitor, as a result of the coupling reaction. While many such compounds are not commonly referred to as couplers, it is convenient to consider them as such in view of the similarities in the ways they and couplers react during photographic processing. For the purposes of the present invention, they are considered couplers. Representative couplers are described in such patents and published patent applications as U.S.
  • Couplers When intended for incorporation in photographic elements, couplers are commonly dispersed therein with the aid of a high boiling organic solvent, referred to as a coupler solvent. Couplers are rendered nondiffusible in photographic elements, and compatible with coupler solvents, by including in the coupler molecule a group referred to as a ballast group. This group is located on the coupler in a position other than the coupling position and imparts to the coupler sufficient bulk to render the coupler nondiffusible in the element as coated and during processing. It will be appreciated that the size and nature of the ballast group will depend upon the bulk of the unballasted coupler and the presence of other substituents on the coupler.
  • a photographic element comprising a support, a photographic silver halide emulsion and associated therewith a non-diffusible photographic coupler which reacts with oxidized colour developing agent to give a compound which may or may not be an image dye, characterized in that the coupler contains a coupling group COUP-bonded at a position other than the coupling position to a ballast which is substituted with a hydroxyphenylsulfonyl or hydroxyphenylsulfinyl group.
  • the coupling group COUP- of the couplers used in the photographic elements of the invention can be any coupling group known or used in the art to form a colored or colorless reaction product with oxidized color developing agent.
  • the ballast group of the couplers used in the invention can be any ballast, or portion thereof, which is substituted with a hydroxyphenylsulfonyl group or hydroxyphenylsulfinyl group with the exception of couplers of the formula: wherein
  • ballast groups used in the invention am substituted with a group of the structural formula: where
  • the substituted group can be joined to the coupling group COUP- at any position, other than the coupling position, where ballast groups commonly are joined.
  • the coupling position of the coupling group can be unsubstituted, or substituted with a coupling off group which can modify the equivalency of the coupler, its reactivity, its dispersibility or which, upon release from the coupler, interacts with other components of the element.
  • the coupling group can include substituents in other positions.
  • ballast groups used in the invention have the structural formula: wherein
  • the bivalent linking group represented by L L 2 and L 3 can be any of the groups found in ballast groups, such as alkylene of up to 10 carbon atoms, arylene of 6 to 10 carbon atoms, heterocyclene of 5 to 10 carbon atoms, may include oxygen, sulfur, amino, amido, sulfonamido, carbamoyl, sulfamoyl, and combinations of such linking groups, e.g. alkarylene, aralkylene, aminoarylene, aminoalkylene, amidoarylene, amidoalkylene, ureido, alkarylamido, amidoarylsulfamoyl, aminoarylamido and aminoarylsulfamoylalkyl.
  • ballast groups such as alkylene of up to 10 carbon atoms, arylene of 6 to 10 carbon atoms, heterocyclene of 5 to 10 carbon atoms, may include oxygen, sulfur, amino, amido, sulfonamido, carbamo
  • the hydroxy group in structural formulae II and III is in the para position.
  • alkyl, alkylene, aryl, arylene and heterocyclene groups can be unsubstituted or substituted with one or more groups such as halogen, nitro, amino, carboxy, alkyl, alkoxy, aryl, aryloxy, heterocyclyl, carbamoyl, amido, sulfamoyl and sulfonamido.
  • common yellow dye-forming couplers are acylacetanilides such as pivalylacetanilides and benzoylacetanilides.
  • Common magenta dye-forming couplers are pyrazolones, pyrazolotriazoles, pyrazolobenzimidazoles and indazolones.
  • Common cyan dye-forming couplers are phenols and naphthols, common neutral dye-forming couplers are resorcinols and m-aminophenols.
  • Couplers are acyclic and cyclic compounds in which the active position, corresponding to the coupling position, is adjacent to or in conjugation with a carbon group or an imino group, such as a- or y-substituted ketones or imines, e.g. cyclopentanones, cyclohexanones, indanones, indanoimines, oxyindoles and oxazolinones.
  • These couplers can form the coupling group COUP in the above formulae. Structures of representative coupling groups are shown below.
  • Z represents hydrogen or coupling-off group and the unsatisfied bond, or bonds, indicates the preferred position, or positions, at which there can be attached the remainder of the molecule shown in the above structures; it being recognized that the coupling group can contain other substituents.
  • Typical suitable coupling groups that can be used in the photographic elements of the invention are set out below.
  • (B represents a blocking group capable of being removed during processing, e.g., by alkaline cleavage or coupling)
  • ballasts of general structures B 1 through B 6 where Y is -OH.
  • Cyan dye-forming couplers used in the invention including the following; the group Y in B 2 , B 3 and B 4 being -OH:
  • Magenta dye-forming couplers used in the invention including the following, the group Y in B 2 or B 3 being OH:
  • Yellow dye-forming couplers used in the invention include the following, the group Y in B 1 , B 2 or B 6 being -OH:
  • Noncolor forming couplers used in the invention include the following:
  • Couplers used in the invention can be prepared by attaching a blocked hydroxyphenylsulfonyl or blocked hydroxyphenylsulfinyl group directly to the coupling group or by attaching such a group to the remainder of the ballast group after which the ballast group is attached to the coupling group. Thereafter the blocking group is removed. Conventional condensation reactions can be employed in joining the various groups which ultimately form the coupler. For many of the couplers used in the invention it is convenient to provide the hydroxyphenylsulfonyl group using a 4,4'-sulfonyldiphenol mono ether (e.g. benzyl ether) or mono ester (e.g.
  • acetyl ester Conventional reaction techniques can be employed to attach such a compound to the remainder of the ballast group and the thus formed ballast group to the coupling group. Thereafter, the blocking group can be removed by hydrogenation (in the case of the ether) or alkaline hydrolysis (in the case of an ester).
  • the coupler, or the remainder of the ballast group has an amino group available for reaction, it is convenient to react that amino group with a blocked hydroxybenzenesulfonyl chloride after which the blocking group is removed.
  • couplers used in the invention can be used in the ways and for the purposes that nondiffusible couplers are used in the photographic art.
  • the couplers are incorporated in silver halide emulsions and the emulsions coated on a support to form the photographic elements of the invention.
  • the couplers can be incorporated in photographic layers adjacent a silver halide emulsion layer where, during development, the coupler will be in reactive association with development products such as oxidized color developing agent.
  • the term "associated therewith" signifies that the coupler is in the silver halide emulsion or in an adjacent location where, during processing, it will come into reactive association with silver halide development products.
  • the photographic elements of the invention can be single color elements or multicolor elements.
  • Multicolor elements contain dye image-forming units sensitive to each of the three primary regions of the spectrum.
  • Each unit can be comprised of a single emulsion layer or of multiple emulsion layers sensitive to a given region of the spectrum.
  • the layers of the photographic element, including the layers of the image-forming units, can be arranged in various orders as known in the art.
  • the emulsions sensitive to each of the three primary regions of the spectrum can be disposed as a single segmented layer, e.g., as by the use of microvessels as described in Belgian Patent 881,513.
  • a typical multicolor photographic element of the invention comprises a support bearing a cyan dye image-forming unit comprised of at least one red-sensitive silver halide emulsion layer having associated therewith at least one cyan dye-forming coupler, a magenta dye image-forming unit comprising at least one green-sensitive silver halide emulsion layer having associated therewith at least one magenta dye-forming coupler and a yellow dye image-forming unit comprising at least one blue-sensitive silver halide emulsion layer having associated therewith at least one yellow dye-forming coupler, at least one of the couplers in the element being a coupler as described above.
  • the element can contain additional layers, such as filter layers, interlayers, overcoat layers, subbing layers, and the like.
  • the silver halide emulsions employed in the photographic elements of this invention can be either negative-working or positive-working. Suitable emulsions and their preparation are described in 'Research Disclosure' Sections I and II and the publications cited therein. Suitable vehicles for the emulsion layers and other layers of elements of this invention are described in Research Disclosure Section IX and the publications cited therein.
  • couplers used in the invention can be used. These couplers can be incorporated in the elements and emulsions as described in Research Disclosure Section VII, paragraph C and the publications cited therein.
  • the photographic elements of this invention or individual layers thereof can contain brighteners (see Research Disclosure Section V), antifoggants and stabilizers (see Research Disclosure Section VI), antistian agents and image dye stabilizer (see Research Disclosure Section VII, paragraphs I and J), light absorbing and scattering materials (see Research Disclosure Section VIII), hardeners (see Research Disclosure Section XI), plasticizers and lubricants (see Research Disclosure Section XII), antistatic agents (see Research Disclosure Section XIII), matting agents (see Research Disclosure Section XVI) and development modifiers (see Research Disclosure Section XXI).
  • brighteners see Research Disclosure Section V
  • antifoggants and stabilizers see Research Disclosure Section VI
  • antistian agents and image dye stabilizer see Research Disclosure Section VII, paragraphs I and J
  • light absorbing and scattering materials see Research Disclosure Section VIII
  • hardeners see Research Disclosure Section XI
  • plasticizers and lubricants see Research Disclosure Section XII
  • antistatic agents see Research Disclosure Section XIII
  • matting agents see Research Disclosure
  • the photographic elements of the invention can be coated on a variety of supports as described in Research Disclosure Section XVII and the references described therein.
  • Photographic elements of the invention can be exposed to actinic radiation, typically in the visible region of the spectrum, to form a latent image as described in Research Disclosure Section XVIII and then processed to form a visible dye image as described in Research Disclosure Section XIX.
  • Processing to form a visible dye image includes the step of contacting the element with a color developing agent to reduce deveopable silver halide and oxidize the color developing agent. Oxidized color developing agent in turn reacts with the coupler to yield a dye.
  • Preferred color developing agents are p-phenylene diamines.
  • 4-amino-N,N-diethyl-aniline hydrochloride 4-amino-3-methyl-N,N-diethylniline hydrochloride, 4-amino-3-methyl-N(ethyl-N-(3-(methanesulfonamido) ethylaniline sulfate hydrate, 4-amino-3-methyl-N-ethyl-N-(3-hydroxyethylaniline sulfate, 4-amino-3-(3-(methanesulfonamido)ethyl-N,N-diethyl-aniline hydrochloride and 4-amino-N-ethyl-N-(2-methoxy ethyl)-m-toluidine di-p-toluene sulfonic acid.
  • this processing step leads to a negative image.
  • this step can be preceded by developing exposed silver halide with a non-chromogenic developing agent without forming a dye, and then uniformly fogging the element to render unexposed silver halide developable.
  • a direct positive emulsion can be employed to obtain a positive image.
  • This phenolic acid was acetylated by dissolving in 70 ml acetic anhydride and 7 ml concentrated surfuric acid, stirring 30 minutes at 20°C., then on a steam bath for 30 minutes, cooling, and pouring into 81 water.
  • Refluxing 35 g (0.07 mol) of this acid in excess thionyl chloride for 5 h and concentrating yielded a colorless oil, which on trituration in ligroin gave 22 g white solid (B 2 CI, Y OAc), mp 66-69°C.
  • ballast group containing an amine function may be attached according to Scheme III:
  • Photographic elements of this invention and control elements were prepared and tested according to the procedures described below.
  • All photographic elements were prepared by coating a cellulose acetate butyrate film support with a photosensitive layer containing a silver bromo-iodide emulsion at 0.91 g Ag/m 2 (when the coupler is 4-equivalent) or 0.46 g Ag/m 2 (when the coupler is 2-equivalent), gelatin at 3.78 g/m 2 , and one of the couplers identified in Table I dispersed in one-half its weight of the coupler solvent described and coated at 1.62 x 10- 3 moles/m 2 .
  • the photosensitive layer was overcoated with a layer containing gelatin at 1.08 g/m 2 and bis-vinyl-sulfonylmethyl ether at 1.75 weight percent based on total gelatin.
  • Samples of each element were imagewise exposed through a graduated-density test object and processed at 40°C employing one of three color developing solutions identified below then stopped, bleached, fixed and washed.
  • magenta dye images were produced which were evaluated by plotting dye density vs. log exposure sensitometric curves and recording the maximum dye density (D max ) and gamma (y) i.e., the contrast determined by the slope of the straight line portion of the curve. Additionally, dye hues were evaluated from spectrophotometric curves by measuring the maximum absorption peak ( ⁇ max ) normalized to a density of 1.0 and the half band width (HBW). Halfband width is the width, in nanometers, of the spectrophotometric curve at one-half the difference between maximum density and stain.
  • top- band width (TBW) and bottom-band width (BBW) of the curve were measured at three-fourths and one-fourth, respectively, of the normalized density.
  • Curve shape factor (CSF) equals 100 x TbW/HBW and provides a ratio of the width near the top and bottom of the absorption curve. The greater this ratio, the steeper are the sides of the absorption peak, and the more efficient is the dye's absorption of light in its spectral region.
  • couplers of this invention have enhanced activity, which results in increased maximum dye density and gamma.
  • many of the dyes formed from couplers of this invention have absorption maxima at desirably longer wavelengths and have broader half band widths and larger curve shape factors, resulting in more efficient spectral absorption.
  • Photographic elements containing additional couplers were prepared, processed and evaluated as described above in connection with Examples 1-14. The results are reported in Table II below.
  • photographic elements were prepared as described above in connection with Examples 1-14. Four samples from each element were exposed as described above. One pair of the exposed elements was developed in developer D-2, described above, and the other pair was developed in this developer to which had been added 1.5 g/i of the soluble competing coupler citrazinic acid. The remaining processing for one element from each pair was stopping, bleaching, fixing and washing while for the second element from each pair the bleaching step was omitted so that the developed silver remained in the element. For those elements in which the silver remained, the amount of developed silver, in g/m 2 , was determined by x-ray fluorescence analysis and plotted against exposure. For those elements from which the developed silver had been removed, dye density vs exposure curves were generated.
  • the couplers employed had the following structure:

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
EP19820304461 1981-08-25 1982-08-24 Photographic elements containing ballasted couplers Expired EP0073636B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US29608681A 1981-08-25 1981-08-25
US296086 1981-08-25

Publications (3)

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EP0073636A1 EP0073636A1 (en) 1983-03-09
EP0073636B1 EP0073636B1 (en) 1987-03-18
EP0073636B2 true EP0073636B2 (en) 1992-09-09

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EP (1) EP0073636B2 (enrdf_load_stackoverflow)
JP (1) JPS5842045A (enrdf_load_stackoverflow)
DE (1) DE3275761D1 (enrdf_load_stackoverflow)

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FR2746391B1 (fr) 1996-03-22 1998-04-17 Oreal Compositions cosmetiques a base de pyrazolin-4,5-diones, nouvelles pyrazolin-4,5 diones, procedes de preparation et utilisations
FR2746310B1 (fr) 1996-03-22 1998-06-12 Oreal Compositions de teinture des fibres keratiniques contenant des pyrazolin-3,5-dione ; leur utilisation pour la teinture comme coupleurs, procede de teinture
FR2746306B1 (fr) 1996-03-22 1998-04-30 Oreal Compositions de teinture des fibres keratiniques contenant des pyrazolo-azoles ; leur utilisation pour la teinture comme coupleurs, procede de teinture
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FR2746307B1 (fr) 1996-03-22 1998-04-30 Oreal Compositions de teinture des fibres keratiniques contenant des pyrrolo-azoles ; utilisation comme coupleurs ; procede de teinture
JP3584119B2 (ja) 1996-04-05 2004-11-04 富士写真フイルム株式会社 ハロゲン化銀カラー写真感光材料
FR2772379B1 (fr) 1997-12-16 2000-02-11 Oreal Compositions de teinture des fibres keratiniques contenant des pyrazolo-azoles; leur utilisation pour la teinture comme base d'oxydation, procede de teinture; nouveaux pyrazolo-azoles
FR2786092B1 (fr) 1998-11-20 2002-11-29 Oreal Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition
FR2786094B1 (fr) 1998-11-20 2001-01-12 Oreal Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition
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FR2805737B1 (fr) 2000-03-06 2003-01-03 Oreal Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition
FR2806299B1 (fr) 2000-03-14 2002-12-20 Oreal Compositions pour la teinture des fibres keratiniques contenant des derives de paraphenylenediamine a groupement pyrrolidinyle
JP4369876B2 (ja) 2004-03-23 2009-11-25 富士フイルム株式会社 ハロゲン化銀感光材料および熱現像感光材料
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JP5106285B2 (ja) 2008-07-16 2012-12-26 富士フイルム株式会社 光硬化性組成物、インク組成物、及び該インク組成物を用いたインクジェット記録方法
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JPS516551A (ja) * 1974-07-05 1976-01-20 Fuji Photo Film Co Ltd Karaashashinkankozairyo
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JPS5930262B2 (ja) * 1978-11-14 1984-07-26 富士写真フイルム株式会社 ハロゲン化銀写真感光材料

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EP0073636A1 (en) 1983-03-09
JPS5842045A (ja) 1983-03-11
EP0073636B1 (en) 1987-03-18
DE3275761D1 (en) 1987-04-23
JPH0551889B2 (enrdf_load_stackoverflow) 1993-08-03

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