EP0759190A1 - Derives n-alkylhydroxylamines, utilisation de ces derives comme antioxydants dans des revelateurs photographiques chromogenes et procedes de traitement - Google Patents

Derives n-alkylhydroxylamines, utilisation de ces derives comme antioxydants dans des revelateurs photographiques chromogenes et procedes de traitement

Info

Publication number
EP0759190A1
EP0759190A1 EP96909583A EP96909583A EP0759190A1 EP 0759190 A1 EP0759190 A1 EP 0759190A1 EP 96909583 A EP96909583 A EP 96909583A EP 96909583 A EP96909583 A EP 96909583A EP 0759190 A1 EP0759190 A1 EP 0759190A1
Authority
EP
European Patent Office
Prior art keywords
hydroxylamine
isopropyl
acid
carbon atoms
color
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.)
Withdrawn
Application number
EP96909583A
Other languages
German (de)
English (en)
Inventor
Elizabeth Gertrude c/o Eastman Kodak Co. BURNS
Carl Anthony C/O Eastman Kodak Co. Marrese
Thomas Henry c/o Eastman Kodak Co. Jozefiak
Lynda Woedy C/O Eastman Kodak Co. Mcgarry
Lee Hamilton c/o Eastman Kodak Co. Latimer
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
Original Assignee
Eastman Kodak Co
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 Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of EP0759190A1 publication Critical patent/EP0759190A1/fr
Withdrawn legal-status Critical Current

Links

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
    • G03C7/407—Development processes or agents therefor
    • G03C7/413—Developers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
    • C07C239/08—Hydroxylamino compounds or their ethers or esters
    • C07C239/18—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl

Definitions

  • the present invention relates to color photographic developer compositions and to their use in the processing of silver halide color photographic materials. More specifically, it relates to a color developer composition having certain water-soluble substituted dialkylhydroxylamines as antioxidants which provide stability for the color developer. These compositions and methods are useful in the field of photography.
  • the invention also relates to a novel class of hydroxylamines.
  • Photographic color developing compositions are used to process color photographic materials such as color photographic films and papers to provide the desired color images.
  • Such compositions generally contain developing agents, for example 4-amino-3- methyl-N- ( ⁇ -methane sulfonamidoethy1) aniline, as reducing agents to react with suitable color forming couplers to form the desired dyes.
  • developing agents are susceptible to oxidation by dissolved oxygen.
  • An antioxidant is conventionally included in the developer compositions to preserve the oxidation state of the color developer and thereby maintain useful color developer activity.
  • antioxidants include hydroxylamines, hydroxamic acids, oxi es, nitroxy radicals, hydraz ' ines, hydrazides, phenols, saccharides, various simple amines, polyamines, quaternary ammonium salts, -hydroxy ketones, alcohols, diamides and disulfonamides .
  • antioxidants must be soluble in aqueous media, non- toxic to living organisms, low cost and non-silver halide developers. Further, it is desirable that antioxidants react slowly with oxygen and rapidly with oxidized color developer, but not so rapidly that color development is retarded. Yet another concern is that the antioxidant must not be able to promote bacterial growth.
  • US-A-4, 892, 804 describes a number of dialkylhydroxylamines useful as color developer antioxidants, including N,N- diethylhydroxylamine, which are improvements over the unsubstituted or mono-substituted hydroxylamines.
  • US- A-4,876,174 describes a lengthy list of substituted hydroxylamines believed useful as antioxidants in color developer compositions, but the compounds actually used emit unpleasant odors.
  • water- solubilizing groups such as carboxy and sulfo are shown on dialkylhydroxylamines.
  • Specifically illustrated compounds include N-ethyl-N-ethylsulfonyl- hydroxylamine and N, -ethylsulfonylhydroxylamine.
  • a photographic color developer composition having a pH of from 9 to 13 and comprising a primary aromatic amine color developing agent, the composition characterized as further comprising a hydroxylamine derivative as defined below.
  • This invention also provides a method for .processing a color photographic element comprising developing an imagewise exposed color photographic element with the photographic color developer composition described above.
  • This invention provides novel hydroxylamine derivatives characterized as having the formula [R-CH(R 1 )] m -N(OH)-[R 2 -X] n
  • R and R are independently alkyl of 1 to 8 carbon atoms provided the total carbon atoms for R and
  • R is alkylene of 2 to 6 carbon atoms or phenylene
  • X is sulfo, carboxy, phosphono, -SO NR R or
  • the color developer composition of this invention provides a number of significant advantages including less or no odor and improved stability of the color developer.
  • the improved stability is evidenced by either reduced loss in color developing agent activity or reduced decrease in pH (pH drop) , or both.
  • FIGURE 1 is a graphical representation of the change in color developer agent activity over time for various color developer compositions as described below in Example 3.
  • FIGURE 2 is a graphical representation of the change in color developer composition pH over time for various color developer compositions as described below in Example 3.
  • novel compounds of this invention that are useful as antioxidants in the present invention can be represented by the formula:
  • R and R are independently alkyl (linear or branched) of 1 to 8 carbon atoms (such as methyl, ethyl, n-propyl, isopropyl, isobutyl, t-butyl, n- butyl, pentyl, hexyl, 2-ethylhexyl and octyl) .
  • the ⁇ total number of carbon atoms for both R and R is no
  • each of R and R has 1 to
  • each is methyl i or ethyl.
  • R and R is methyl. It is clear from the noted formula that certain embodiments, one substituent of the nitrogen atom is a branched alkyl group wherein the carbon atom directly connected to the nitrogen has one and only one hydrogen atom.
  • R and R can be substituted with one of more substituents other than sulfo or carboxy groups, as long as such substituents do not adversely affect the antioxidant properties of the compound.
  • each of R and R is an unsubstituted alkyl group (linear or branched) .
  • R is a substituted or unsubstituted, branched or linear alkylene group of 2 to 6 carbon atoms (such as ethylene, trimethylene, isopropylene, tetramethylene and hexamethylene) and preferably, it has only 2 or 3 carbon atoms.
  • R is substituted or unsubstituted
  • the R group can also be a substituted or unsubstituted phenylene group.
  • R examples include hydroxy, carbonamido, carboxy, sulfo, halo, sulfonamido or phosphono.
  • R is an unsubstituted, linear alkylene group of 2 to 4 carbon atoms or
  • R is unsubstituted alkylene of 2 or 3 carbon atoms, and most preferably, it is unsubstituted ethylene.
  • X is sulfo, carboxy
  • R and R are independently hydrogen, or a substituted or unsubstituted alkyl of 1 to 3 carbon
  • R and R are both hydrogen or the same alkyl group of 1 or 2 carbon atoms, and more preferably, they are each hydrogen or methyl.
  • m is 0 or 1
  • n is
  • m is 1 and n is 1, so that the compounds have a branched alkyl substituent attached to the nitrogen 2 atom as well as the -R -X group attached to the nitrogen atom.
  • m is 0 and n is 2 so that the compounds have symmetrical -R 2 -X groups.
  • X is -CONR 3 R 4 only.
  • Suitable monovalent cations or ester groups for the free acids include ammonium (including quaternary amines) , alkali metal ion (such as sodium, potassium or lithium) , alkyl having 1 to 4 carbon atoms (such as methyl, ethyl, n-propyl, isopropyl, n- butyl and t-butyl) , pyridinium, tetraethylammonium and tetramethylammonium, as well as other cations and ester groups which would be readily apparent to one skilled in the art.
  • methyl ester, ethyl ester or an alkali metal salt form is used.
  • Representative compounds useful in the practice of this invention include N-isopropyl-N- ethylsulfonic acid hydroxylamine, N-isopropyl-N- isopropylsulfonic acid hydroxylamine, N-isopropyl-N- n-propylsulfonic acid hydroxylamine, N-isopropyl-N- t- butylsulfonic acid hydroxylamine, N-sec-butyl-N- ethylsulfonic acid hydroxylamine, N-sec-butyl-N- isopropylsulfonic acid hydroxylamine, N-sec-butyl-N- n-butylsulfonic acid hydroxylamine, N-N-ethylsulfonic acid, N-2-octyl-N-n-propylsulfonic acid, N-isopropyl- N- (sulfonamidoethyl)hydroxylamine, N-is
  • N-isopropyl-N- ethylsulfonic acid hydroxylamine N-isopropyl-N- propionic acid hydroxylamine
  • N-isopropyl-N- (carbonamidoethyl)hydroxylamine bis (N,N- carbonamidoethyl)hydroxylamine
  • N-isopropyl-N- (N,N- dimethylsulfonamidoethyl)hydroxylamine are preferred, along with salts or esters of the free esters.
  • one useful synthetic procedure for sulfo-substituted compounds comprises reacting an N-alkylhydroxylamine with a vinylsulfonate in a suitable solvent (such as water, an alcohol, tetrahydrofuran or methyl ethyl ketone) .
  • a suitable solvent such as water, an alcohol, tetrahydrofuran or methyl ethyl ketone
  • water is the best solvent.
  • the antioxidant is included in the color developer composition of this invention in an amount of at least 0.001 mol/1, and a preferred amount is from 0.005 to 0.5 mol/1. More than one antioxidant can be used in the same color developer composition if desired, but preferably, only one is used.
  • the pH of the color developer composition is generally from 9 to 13 (preferably from 9 to 11) , as provided by the addition of one or more weak or strong bases (such as a hydroxide) or buffers in amounts readily known in the art.
  • weak or strong bases such as a hydroxide
  • Particularly useful buffers include, but are not limited to, carbonates, borates, tetraborates, phosphates, glycine salts, leucine salts, valine salts, proline salts, alanine salts, aminobutyric acid salts, lysine salts, guanine salts and hydroxybenzoates .
  • the color developer compositions of this invention include one or more color developing agents, of which there are hundreds of possibilities.
  • Useful classes of such materials include, but are not limited to, aminophenols, p-phenylenediamines
  • the color developer composition can be easily prepared by mixing a suitable color developer (in a suitable solution) with an antioxidant as described above (in a suitable aqueous solution) . Water can be added to the resulting solution to provide the desired concentrations of an aqueous solution, and the pH can be adjusted as noted above.
  • the composition can also include one or more of a variety of other addenda which are commonly used in such compositions, such as alkali metal halides (such as potassium chloride, potassium bromide, sodium bromide and sodium iodide) , metal sequestering agents (such as polycarboxylic or aminopolycarboxylic acids or polyphosphonates) , buffers (as noted above) , other preservatives (such as sulfites) , anti-foggants, development accelerators, optical brighteners, wetting agents, stain reducing agents, surfactants, defoaming agents, and water-soluble or water-dispersible color couplers, as would be readily understood by one skilled in the art (see for example, Research Disclosure, noted above and US-A-4, 814,260) .
  • the amounts of such additives are well known in the art also.
  • the amounts of halides can be varied widely, but are preferably in the range of
  • Example 1 A preferred color developing composition is described below in Example 1.
  • the color developing composition is preferably formulated and used as an aqueous solution, either as the working developer solution or a replenishing solution.
  • color developer composition can also be formulated as used as dry tablets.
  • the technology for this embodiment is readily known in the art, such as US-A-5,362, 610, US-A-5, 376, 509 and EP-A-0 611 986A1.
  • the color developing composition of this invention has obvious utility to provide color development in an imagewise exposed color photographic element comprising a support and one or more silver halide emulsion layers containing an imagewise distribution of developable silver halide emulsion grains.
  • a wide variety of types of photographic elements (both color films and papers) containing various types of emulsions can be processed using the present invention, the types of elements being well known in the art (see Research Disclosure, noted above) .
  • the invention can be used to process color photographic papers of all types of emulsions, including so-called “high chloride” and “low chloride” type emulsions, and so-called tabular grain emulsions as well.
  • the color developer solution can also be used in color reversal processing.
  • the present invention is particularly useful to process high chloride (greater than 70 mole % chloride and preferably greater than 90 mole % chloride) emulsions in color photographic papers.
  • Such color photographic papers can have any useful amount of silver coated in the one or more emulsions layers, and in some embodiments, low silver elements
  • the layers of the photographic elements can have any useful binder material or vehicle as it known in the art, including various gelatin and other colloidal materials .
  • One useful binder material is acid processed gelatin which can be present in any layer in any suitable amount.
  • Development is carried out by contacting the element under suitable time and temperature conditions, in suitable processing equipment, to produce the desired developed image. Additional processing steps can then be carried out using conventional procedures, including but not limited to, one or more development stop, bleaching, fixing, bleach/fixing, washing (or rinsing) , stabilizing and drying steps, in any particular desired order as would be known in the art. Useful processing steps, conditions, materials and amounts useful therefor are well known (see for example, Research Disclosure and references cited therein) .
  • the photographic elements processed in the practice of this invention can be single or multilayer color elements.
  • Multilayer color elements typically contain dye image-forming units sensitive to each of the three primary regions of the visible spectrum. Each unit can be comprised of a single emulsion layer or multiple emulsion layers sensitive to a given region of the spectrum.
  • the layers of the element can be arranged in any of the various orders 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.
  • the elements can also contain other conventional layers such as filter layers, interlayers, subbing layers, overcoats and other layers readily apparent to one skilled in the art.
  • a magnetic backing can be used as well as conventional supports .
  • Particularly useful color photographic papers that can be used in the practice of this invention include, but are not limited to, KODAK EKTACOLOR EDGE ® 2 Paper, KODAK EKTACOLOR PORTRA ® II Paper, AGFACOLOR PROFESSIONAL SIGNUM Paper, AGFACOLOR Paper Type 10, FUJICOLOR SUPER FA Type P Paper, KONICA COLOR QA Paper Type A6 and KONICA COLOR QA Paper Professional Type P5.
  • the elements are typically exposed to suitable radiation to form a latent image and then processed to form a visible dye image. Processing includes the step of color development in the presence of a color developing agent to reduce developable silver halide and to oxidize the color developing agent. Oxidized color developing agent in turn reacts with a color-forming coupler to yield a dye.
  • Processing according to the present invention can be carried out using conventional deep tanks holding processing solutions. Alternatively, it can be carried out using what is known in the art as "low volume thin tank” processing systems, or LVTT, which have either a rack and tank or automatic tray design. Such processing methods and equipment are described, for example, in US-A-5,436, 118 and publications noted therein.
  • the length of time and temperatures used for each processing step of the present invention are generally those conventionally used in the art.
  • development is generally carried out at a temperature of from 20 to 50 °C.
  • the overall processing time (from development to final rinse or wash) can be from 30 seconds to 40 minutes, and each step can be from 10 to 450 seconds.
  • Short overall processing times that is, less than 140 seconds, are desired for processing color photographic papers. It is particularly desirable that the time for development using the color developing composition of this invention be less than 200 seconds, and preferably, less than 120 seconds, but longer or shorter times may be useful under particular conditions .
  • the following examples are provided to illustrate the practice of this invention and not to limit it in any way. Unless otherwise indicated, percentages are by weight.
  • the C NMR had peaks at 59.4, 52.4, 49.9 and 19.2 ppm.
  • the sodium analysis was 11.5%.
  • (sulfonamidoethyl)hydroxylamine, N-isopropyl-N- (N,N- dimethylsulfonamidoethyl)hydroxylamine, and N- isopropyl-N- (N,N-diethylsulfonamidoethyl) - hydroxylamine were prepared using similar conditions and slightly varying solvent mixtures of water and methanol, water and tetrahydrofuran or tetrahydrofuran and N,N-dimethylformamide. These compounds were prepared by reacting vinylsulfonamide, N,N-dimethyl vinylsulfonamide or N,N-diethyl vinylsulfonamide with N-isopropylhydroxylamine, as would be appropriate.
  • reaction mixture became an orange, viscous mixture, which was transferred to another vessel and allowed to cool to room temperature. After 14 hours, the mixture had solidified. The solid was collected and dried under vacuum overnight to give 105 g of white solid for analysis.
  • This example demonstrates the preparation of a preferred aqueous photographic color developer composition according to this invention.
  • KODAK EKTAPRINTTM2 Stain Reducing Agent l g N-isopropyl-N-ethylsulfonic acid hydroxylamine, 0.041 mol sodium salt antioxidant
  • Example 3 Stability Comparisons The color developer composition of Example
  • Control A composition was like Example 1 except that the antioxidant was omitted.
  • the Control B composition contained N,N-diethylhydroxylamine as the antioxidant.
  • the Control C and D compositions contained N,N-diethylsulfonic acid hydroxylamine and N-ethyl-N-ethylsulfonic acid hydroxylamine, respectively, as the antioxidants.
  • Each color developer composition was subjected to an "aeration" test designed to measure the concentration of color developer as a function of time as the composition (1 liter) was continuously
  • composition 2-Day Loss 4-Day 2-Day pH 4-Day pH
  • Control B 1.40 g 4.00 g 0.13 0.16
  • FIGURE 1 It can be seen in FIGURE 1 that the concentration of color developer dropped less quickly with using the present invention.
  • the color developer loss is considered to be significantly less with the practice of this invention compared to the use of similar art-recognized antioxidants (Controls B-D) . Without an antioxidant (Control A) , the loss of color developer is also significant.
  • FIGURE 2 It is apparent from FIGURE 2 that the change in pH (that is, pH decrease) is significantly less over time with the present invention compared to the use of compositions containing no antioxidant or similar sulfo-substituted antioxidants (Controls A, C and D) .
  • the Control B composition had a similar pH drop over time, but the combined data shown in both FIGURES indicates that the present invention showed considerable overall improvement in performance.
  • Color developer compositions like that in Example 1 except with various antioxidants were compared as to their stability, that is, the loss in color developing agent activity, and pH drop. Each color developer composition was subjected to an accelerated aerial oxidation as follows:
  • a 50 ml volume of the color developer solution was placed into a 50 ml graduated cylinder (2 cm diameter, 21 cm height) .
  • a glass tube (0.4 cm inner diameter, 0.6 cm outer diameter) was placed into the solution and suspended so that the tip was held 1 cm above the bottom of the graduated cylinder. Water saturated air was passed through the glass tube at a rate of 25 ml/min.
  • the color developer solution was sampled every 24 hours and the concentration of color developing agent and pH were determined. Generally the color developer solution was nearly exhausted after 5 days of aeration and the test was halted. East test was done in duplicate, and the results were averaged. - 20 -
  • Example 4 N-isopropyl-N- (N,N- dimethylsulfonamidoethyl)hydroxylamine.
  • Control E bis(N,N- dimethylsulfonamidoethyl)hydroxylamine.
  • Example 5 N-isopropyl-N- (p- carboxybenzyl)hydroxylamine.
  • Control F bis(N,N-p- carboxybenzy1)hydroxylamine.
  • Example 6 N-isopropyl-N-propionic acid hydroxylamine.
  • Control G bis (N,N-propionic acid)hydroxylamine.
  • Example 7 N-isopropyl-N-ethanesulfonic acid hydroxylamine.
  • Control H bis (N,N-ethanesulfonic acid)hydroxylamine.
  • Example 8 N-isopropyl-N- (2-carboxymethylene-3- propionic acid)hydroxylamine.
  • Control I bis (N,N-2-carboxymethylene-3- propionic acid)hydroxylamine.
  • Example 9 N-isopropyl-N- (carbonamidoethyl)hydroxylamine.
  • Example 10 bis(N,N- carbonamidoethyl " )hydroxylamine.
  • Control J N-n-propyl-N- (carbonamidoethyl)hydroxylamine.
  • Example 5 9 29 80 91 0.10 0.13 0.20 0.20
  • Example 7 1 1 35 69 89 0.1 1 0.17 0.24 0.25
  • the hydroxylamine derivatives useful in the present invention provided improved color developing agent stability or less drop in pH or both than the comparable hydroxylamine derivatives in the "Control" experiments.
  • Example 1 The color developer composition described in Example 1 was compared to a similar composition in which N-isopropyl-N-ethylsulfonic acid hydroxylamine, sodium salt was replaced with N-n-propyl-N- ethylsulfonic acid hydroxylamine, sodium salt (Control K) . These two compositions were compared to the ability of the two hydroxylamine derivatives to reduce the loss in color developing agent over a period of time. Each color developer composition was subjected to accelerated aerial oxidation as described for Examples 4-10 above.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
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Abstract

Certains dérivés n-alkylhydroxylamines sont utiles en tant qu'antioxydants dans des compositions de révélateurs photographiques chromogènes. Ces composés stabilisent les compositions de révélateurs et sont extrêmement solubles dans l'eau et pratiquement sans odeur.
EP96909583A 1995-03-09 1996-03-06 Derives n-alkylhydroxylamines, utilisation de ces derives comme antioxydants dans des revelateurs photographiques chromogenes et procedes de traitement Withdrawn EP0759190A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US401584 1989-08-31
US40158495A 1995-03-09 1995-03-09
US61019896A 1996-02-29 1996-02-29
US610198 1996-02-29
PCT/US1996/003016 WO1996028761A1 (fr) 1995-03-09 1996-03-06 Derives n-alkylhydroxylamines, utilisation de ces derives comme antioxydants dans des revelateurs photographiques chromogenes et procedes de traitement

Publications (1)

Publication Number Publication Date
EP0759190A1 true EP0759190A1 (fr) 1997-02-26

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Country Status (3)

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EP (1) EP0759190A1 (fr)
JP (1) JPH10501269A (fr)
WO (1) WO1996028761A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0851289A3 (fr) * 1996-12-23 1998-12-23 Tetenal Photowerk GmbH & Co Développateur couleur
EP0884640A1 (fr) * 1997-06-13 1998-12-16 Eastman Kodak Company Traitement d'éléments phtographiques par des révélateurs photographiques couleur contenant des antioxydants, N,N-dialykalhydroxyalamine

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Publication number Priority date Publication date Assignee Title
US3867445A (en) * 1971-04-13 1975-02-18 Ciba Geigy Corp Substituted hydroxylamine anti-oxidants
JP2648971B2 (ja) * 1989-10-30 1997-09-03 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の処理方法
JP2597206B2 (ja) * 1989-11-13 1997-04-02 富士写真フイルム株式会社 カルボキシアルキル置換ヒドロキシルアミン類の製造方法
US5660974A (en) * 1994-06-09 1997-08-26 Eastman Kodak Company Color developer containing hydroxylamine antioxidants
EP0687951B1 (fr) * 1994-06-10 2001-10-10 Konica Corporation Composition sous forme de granulés ou comprimés pour le développement en couleurs

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9628761A1 *

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WO1996028761A1 (fr) 1996-09-19
JPH10501269A (ja) 1998-02-03

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