EP0058694A1 - Procede de recuperation d'un additif photographique a partir de sa dispersion. - Google Patents

Procede de recuperation d'un additif photographique a partir de sa dispersion.

Info

Publication number
EP0058694A1
EP0058694A1 EP81902384A EP81902384A EP0058694A1 EP 0058694 A1 EP0058694 A1 EP 0058694A1 EP 81902384 A EP81902384 A EP 81902384A EP 81902384 A EP81902384 A EP 81902384A EP 0058694 A1 EP0058694 A1 EP 0058694A1
Authority
EP
European Patent Office
Prior art keywords
dispersion
active agent
surface active
water
recovering
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.)
Granted
Application number
EP81902384A
Other languages
German (de)
English (en)
Other versions
EP0058694B1 (fr
Inventor
David John Young
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.)
Kodak Ltd
Eastman Kodak Co
Original Assignee
Kodak Ltd
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 Kodak Ltd, Eastman Kodak Co filed Critical Kodak Ltd
Publication of EP0058694A1 publication Critical patent/EP0058694A1/fr
Application granted granted Critical
Publication of EP0058694B1 publication Critical patent/EP0058694B1/fr
Expired 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
    • G03C7/32—Colour coupling substances
    • 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
    • G03C11/00—Auxiliary processes in photography
    • G03C11/24—Removing emulsion from waste photographic material; Recovery of photosensitive or other substances

Definitions

  • This invention relates to a method of recovering a photographic addendum from a dispersion thereof.
  • a water- insoluble organic compound into a hydrophilic colloid layer of a photographic sheet material (which may or may not be light-sensitive) in such a way that the compound cannot diffuse within or away from that layer.
  • a photographic sheet material which may or may not be light-sensitive
  • One method which has been employed for preventing diffusion of an incorporated organic compound in a hydrophilic colloid layer comprises dispersing the compound in admixture with a high-boiling, water-immisible, organic solvent.
  • a solvent which need not be liquid at room temperature, is often referred to, and is referred to herein, as an 'oil-former' (see for instance United Kingdom patent specification No. 541,589).
  • This method is carried out by dispersing the mixture of organic compound and oil-former in an aqueous solution of the hydrophilic colloid with the aid of a surface active agent and subsequently mixing the dispersion so obtained with the other constituents of the coating composition to be used in forming the layer.
  • a method which has been proposed for recovering water-insoluble photographic addenda from dispersions thereof in aqueous media containing a protainaceous colloid and a surface active agent comprises treating the dispersion with an enzyme to degrade the colloid, and a substance which causes precipitation of the addendum (see Research Disclosure September 1977, Item No. 16101).
  • the substance causing precipitation may be a surface active agent of opposite charge.
  • a method of recovering a water-insoluble organic compound from a dispersion of a mixture thereof with an oil-former in an aqueous medium containing a hydrophilic colloid and a surface active agent which comprises adding to the liquid dispersion an oleophilic non-ionic surface active agent so as to cause crystallization of the organic compound.
  • the method of the invention is very suitable for the recovery of couplers and other compounds (such as redcx dye-releasing compounds) used for image formation in colour photographic materials from their dispersions, and is also useful for recovering such other organic compounds as ultra violet absorbers and dye stabilizing agents.
  • couplers and other compounds such as redcx dye-releasing compounds
  • References giving information on couplers are given in Section VII of Research Disclosure December 1973, Item 17643.
  • the couplers commonly employed in photographic materials are water-insoluble compounds often containing ballast groups, phenolic (including naphtholic) couplers being used for producing cyan dyes and compounds containing an activated methylene group, including both heterocyclic and open-chain compounds, being used for producing magenta and yellow dyes.
  • Important magenta couplers are pyrazolones and important yellow couplers are benzoylacetanilides.
  • Patents describing couplers include the following United States Patents: Cyan dye-forming 2 367 531 3 034 892
  • the compounds are substantially water-insoluble, high-boiling organic crystalloidal materials.
  • esters including organic esters such as di-n-butyl phthalate, and phosphate esters, such as tricresyl phosphate.
  • the oil-former preferably has a boiling point of at least 150oC and is chemically inert in the chosen system. Other desirable properties are listed in the U.K. Specification, together with numerous examples of suitable compounds.
  • the non-ionic surface-active agent used in a method of the invention is oleophilic and preferably has a hydrophile-lipophile balance (HLB) value no greater than 5 but having such a value does not necessarily ensure that an agent will be satisfactory.
  • HLB hydrophile-lipophile balance
  • Methods of determining HLB are described in, for instance, 'Emulsion Science', P.Sherman, Academic Press, London (1968), Chapter 3. In many instances, the HLB of commercially available surface active agents is quoted by the suppliers. It may be noted that the maximum HLB value likely to be found for any surface active agent is approximately 40.
  • Types of surface active agent which have been found effective for the method of the invention include: glycerol esters poiyoxyethylene ethers sorbitan esters. Commercial surface active agents of these types include certain of the agents sold under the trade marks:
  • ncn-ionic surface active agent For a given dispersion, it is necessary to select an optimum ncn-ionic surface active agent and the optimum concentration thereof, by preliminary tasting with small quantities. A mixture of non-ionic surface active agents may in some cases give a synergistic effect.
  • the amount of non-ionic surface active agent required is of the same order as the amou t of addendum and oil-former in the dispersion.
  • the weight of surfactant required is usually from 0.1 to 10 times the total weight of addendum and oil-former.
  • auxiliary solvents are ethyl and butyl acetates, and 2-(2-butoxyethoxy)ethyI acetate.
  • the dispersion is if necessary liquified by melting and the ncn-ionic surface active agent added.
  • Any auxiliary solvent to be used may be added at the same time or later. It is convenient when an auxiliary solvent is used to dissolve the surface active agent in this.
  • the compound to be recovered After the compound to be recovered has crystallised, it may be filtered and washed with warm water to remove the hydrophilic colloid and any water soluble surface-active agent. It may also be washed with an organic solvent having a low solvent power for the compound being recovered but a high solvent power for the oleophilic surface active agent. Hydrocarbon solvents such as petroleum ether, hexane and heptane are suitable in many instances. Often, the dried recovered compound is sufficiently pure for reuse without further treatment.
  • the invention is illustrated by the following
  • Dispersion A The couplers, oil-formers and weights of anionic surfactant in the two dispersions were as follows: Dispersion A
  • Cyan dye-forming coupler 2-[ ⁇ -(2,4-di-tert-amyl- phenoxy)-butyramido]-4,6- dichlcro-5-methylphenol.
  • Oil former dibutylphthalate.
  • Magenta dye-forming coupler 1- ( 2 , 4 , 6- trichlorophenyl ) - 3- ⁇ 5- [ ⁇ -3-tert-butyl-4- hydroxyphenoxy) tetradecane- amido]-2-chloroanilino ⁇ -5- pyrazolone .
  • Oil former tricresylphosphate Weight of anionic surfactant : 5.0 g.
  • R is a long-chain fatty acid group of 12 to 18 carbon atoms.
  • 'Alkanol XC' is believed to be sodium triisopropyl naphthalene sulphonate.
  • the mixture obtained was stirred at 50°C for 8 hours and the precipitated coupler filtered off and washed successively with hot water and heptane.
  • the coupler was recovered in 57% yield and was at least as pure as when incorporated into the original dispersion (measured by high pressure liquid chromatography).
  • the effectiveness of two cationic surface active agents at causing crystallisation of coupler from the dispersions A and 3 used for Example 1 was examined.
  • the cationic agents were: (i) cetyl pyridinium chloride (ii) didodecyldimethylammonium bromide.
  • 10 ml of a 1% w/v aqueous solution of the cationic agent was added to 4 ml of the dispersion and held at 40°C. Samples were examined after 2 and 24 hours using a microscope at X200 magnification and with crossed polarizing filters. The numbers and sizes of crystals observed are expressed qualitatively in the following table.
  • the dispersion A sample treated with cationic surfactant (i) for 24 hours was filtered and the coupler crystals collected represented a recovery of less than 25%.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Separation Of Suspended Particles By Flocculating Agents (AREA)

Abstract

Un additif photographique organique insoluble a l'eau est recupere depuis une dispersion d'un melange de celui-ci avec un formeur d'huile dans un milieu aqueux contenant un colloide hydrophile et un agent tensio-actif par addition d'un agent tensio-actif oleophile non ionique selectionne.
EP81902384A 1980-09-01 1981-09-01 Procede de recuperation d'un additif photographique a partir de sa dispersion Expired EP0058694B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8028150 1980-09-01
GB8028150 1980-09-01

Publications (2)

Publication Number Publication Date
EP0058694A1 true EP0058694A1 (fr) 1982-09-01
EP0058694B1 EP0058694B1 (fr) 1985-07-10

Family

ID=10515760

Family Applications (2)

Application Number Title Priority Date Filing Date
EP81902384A Expired EP0058694B1 (fr) 1980-09-01 1981-09-01 Procede de recuperation d'un additif photographique a partir de sa dispersion
EP81303984A Pending EP0047170A1 (fr) 1980-09-01 1981-09-01 Procédé pour la récupération d'un additif photographique à partir d'une dispersion

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP81303984A Pending EP0047170A1 (fr) 1980-09-01 1981-09-01 Procédé pour la récupération d'un additif photographique à partir d'une dispersion

Country Status (5)

Country Link
US (1) UST102402I4 (fr)
EP (2) EP0058694B1 (fr)
JP (1) JPS57501347A (fr)
DE (1) DE3171315D1 (fr)
WO (1) WO1982000901A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU589614B2 (en) * 1985-04-05 1989-10-19 Konishiroku Photo Industry Co., Ltd. Method of treating photographic waste solutions and automatic photograph processor

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1274048A (en) * 1969-07-30 1972-05-10 Bayer Ag Process for the production of pure basic dyestuffs
IT1066378B (it) * 1976-02-24 1985-03-04 Betz Int Perfezionamento nei procedimenti di separazione per flottazione
JPS5427428A (en) * 1977-08-03 1979-03-01 Fuji Photo Film Co Ltd Recovery method of oil soluble couplers

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8200901A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU589614B2 (en) * 1985-04-05 1989-10-19 Konishiroku Photo Industry Co., Ltd. Method of treating photographic waste solutions and automatic photograph processor

Also Published As

Publication number Publication date
EP0047170A1 (fr) 1982-03-10
JPS57501347A (fr) 1982-07-29
DE3171315D1 (en) 1985-08-14
EP0058694B1 (fr) 1985-07-10
UST102402I4 (en) 1982-11-02
WO1982000901A1 (fr) 1982-03-18

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