US2358053A - Process for the recovery of organic compounds from photographic solutions - Google Patents

Process for the recovery of organic compounds from photographic solutions Download PDF

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Publication number
US2358053A
US2358053A US379906A US37990641A US2358053A US 2358053 A US2358053 A US 2358053A US 379906 A US379906 A US 379906A US 37990641 A US37990641 A US 37990641A US 2358053 A US2358053 A US 2358053A
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Prior art keywords
recovery
solutions
solvent
compounds
photographic
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Expired - Lifetime
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US379906A
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English (en)
Inventor
Karl J Brunings
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to FR962807D priority Critical patent/FR962807A/fr
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US379906A priority patent/US2358053A/en
Priority to GB7809/41A priority patent/GB551028A/en
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Publication of US2358053A publication Critical patent/US2358053A/en
Anticipated expiration legal-status Critical
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29—Development processes or agents therefor
    • G03C5/31—Regeneration; Replenishers

Definitions

  • This invention relates to the recovery of organic compounds from solutions obtained from various photographic processes. More particularly this invention relates to the recovery of tical conditions may be present in the form of free bases.
  • the overflow from these continuous processes contains large amounts of these soluble compounds, and although the solution itself is near exhaustion, or otherwise inefiective due to the formation of various products during the continuous process the compounds themselves may still be used if they can be removed from the solution.
  • Continuous development forms no part of the present invention and is merely mentioned herein to designate one common type of process from which solutions are obtained containing valuable components, heretofore, lost, but from which may be recovered valuable organic compounds, in accordance with my invention.
  • This invention has for one object to provide a process for separating and recovering organic compounds from various developer solutions and the like.
  • a still further object is to provide 'a recovery method for treating photographic solutions to recover organic compounds, therefrom,
  • the compounds are amino compounds from the group consisting of aminophenol and diamines, and especially derivatives thereof. of phenylenediamines wherein the substituents may not only be in the amino groups but may also be on the nucleus, as phenylenediamine For example, there are the derivatives tracts used. However, this method be set forth hereinafter.
  • the organic compounds may also be removed from their solvent solutions by reextraction with, for example, diluted or concentrated acids, and the resultant exanalysis and neutralization of the extract, hence, involves problems of standardization and consequently I, prefer the precipitation procedure which will be illustratedin further detail.
  • the solutions would be treated independently "in myprocess and in some instances a particular solvent might be used for-each solution'or other steps adopted, permitting not only the recovery-of, for example, the developer present-in the solution, but also, rendering it possible to treat the residue from my processin amanner where'still other components may be recovered.
  • a particular solvent might be used for-each solution'or other steps adopted, permitting not only the recovery-of, for example, the developer present-in the solution, but also, rendering it possible to treat the residue from my processin amanner where'still other components may be recovered.
  • the use. of a particular $01 vent for any specific solution sometimes, also gives still improved results. 7
  • these organic compounds may be recovered andmcollected in a more concentrated form; If the solution'in question is already alkaline, extraction withthe solvent in accordance with my invention 'may he proceeded with dif the solution to which my recovery process is to be applied is not in the proper pH condition as obtained, suitable additions are made, as for My preferred method employing precipitation involves the principle that organic bases, dissolved in an inert solventmay be precipitated in the form of their acid salts'by treating'the solutions with gaseous, liquid or solid anhydrous acids, and/or acid anhydrides.
  • the acid salts of the organic bases thus formed are generally completely insoluble in the organic solvent and precipitate outin an easily filterable condition.
  • the organic constituents being recovered are retrieved in a solid state either identical to the substance used and, in general, free from undesired components as harmful oxidation products.
  • the recovered product may be used in subsequent mixes without 7 material changes in formula, and without previous tedious analytical assays.
  • the compound'recovered from the overflow solution can be used in preparing fresh quantities of the initial solution because the compound is in a state particularly suitable for this use.
  • FIG. 1 is a semi-diagrammatic side elevation view, showing one arrangement of apparatus which might be employed for carrying out my process.v
  • Fig. 2 is likewise a semi diagrammatic side elevation view showing one type of change which might be made in my apparatus set-up. It will be noted that the drawing is also somewhat in the nature of flow sheets of my process.
  • Fig. 1, 2 is the feed conduit through which the material to be subjected 'to recovery is supplied to the system.
  • the feed will comprise an aqueous solution.
  • This conduit discharges into the unit 3 positioned upon support 4.
  • the device 3 may comprise a conventional mixer or other type of device for bring ingthe solution in intimate contact with the extracting agent.
  • the showing in Fig. 1 is merely diagrammatic. While the unit hasbeen shown inan elevated position, in order that gravity flow from the apparatus may take place it is possible to place it in a lower position and pump the fluids therefrom. LAISO more than one extractor or mixer unit may be employed. Feeding into the mixer or extractor 3 is another conduit 6 which is connected through pump I to the solvent tank 8.
  • conduit 9 Leading from an intermediate point in mixer 3 is another conduit 9 which goes to the several separator H, l2, and I3. These separators are interconnected in series by means of the conduits l5 and I6. Also, further connections may be made as at l8 and 19. These separators are of the gravity type, being merely elongated chambers in which liquid of the lowest specific gravity becomes the top layer and the liquid of higher specific gravity the lower layer. the units may be considered more or' les comparable to decanters. Suitable provision, not shown, may be made whereby the liquid residue involves In other words 7 in the bottom of the separators may be discharged to other treatment or to waste.
  • the terminal unit in the group discharge through conduit I! through drier I4 and conduit 2
  • This later unit may be placed on a support 23 for facilitating access to the lower portion thereof for removing the contents through conduit 24.
  • Conduit 24 feeds through pump 26 in series and positioned before filter presses orother similar devices 21.
  • pump 26 feeds through pump 26 in series and positioned before filter presses orother similar devices 21.
  • pump 26 feeds through pump 26 in series and positioned before filter presses orother similar devices 21.
  • there may be'several units in the group so that when one filter press is removed from operation other units may be put into operation without a discontinuance of the process.
  • other devices such as thickeners, may be employed for removing the precipitate from the liquid containing it. However accomplished the liquid (solvent) separated in 'unit 21 may be returned through conduit 28 to tank 8.
  • for generating precipitating agent.
  • the exact, construction of this unit would depend upon the particular type material which was to be generated and introduced a substantial distance into the precipitator by means of the internally extending distributing means 32.
  • might comprise more or less a standard hydrochloric acid gas generator such as aKipp type generator, operating on ammonium chloride.
  • aKipp type generator operating on ammonium chloride.
  • would be such as to enable the production of the desired acid and/or anhydride and inject into the precipitator.
  • conduit 33 through which residue components from these units may be withdrawn to further recovery steps or other treatment.
  • Fig.2 I show in this figure'an example of one modification which, in addition to those already referred to may be made in my ap paratus arrangement.
  • this set up 3 represents the mixer already discussed above.
  • a'conduit .41 leading from an intermediate point in the mixer instead of being connected with the separators, as discussed above under Fig. 1 is connected to one or more centrifuge units 42.
  • the centrifuge may be considered merely as gravity separation speeded up. Under some circumsta'nces, for increased capacity or in the handling of extracted mixtures which do not readily or quickly separate by gravity, it, may be desirable to employ forced separation rather than gravity separation.
  • a drier comparable to drier 14 in Fig. 1 could be inserted at some point in the circuits 43, 44, and 45.
  • the subsequent drying step may sometimes be eliminated or reduced tosuch an extent that a smaller drier than [4 may be employed.
  • the dryin unit may comprise simply one or more columns containing a. hygroscopic substance, such as calcium chloride or other drying. agent,
  • Sight glasses, valves and the like may be in.- cluded in the apparatus as desired and an invention is not to be restricted in this respect.
  • the solution to be subjected to my'novel recovery procedure contained an orgame developer.
  • the particular developer was an 'cordance with the preceding description and might be considered a derivative of phenylenedi amine in which alkyl groups had been substituted ⁇ for hydrogen in the amino group and/or at other points in the molecule.
  • the particular nature of the compound, as already pointed out, is not a limitation upon my invention, the process as described in this particular specific example functioning equally well with other-amino compounds such as phenylenediamine derivatives and aminophenol derivatives;
  • the pH 'of the aqueous developing solution necessary for the extraction is dependent upon the type of compound to be recovered, andthe efficiency of extraction desired.
  • the solutions to be treated in this example were held at a fall between 10.5 and 11.5.
  • the solution was violently stirred with a hydrocarbon solvent.
  • the solvent employed was kerosene of a high flash point, obtained commercially from one of the large oil companies.
  • This solvent chemically was usually comprised principally of straight chain hydrocarbons '(dodecane through pentadecane) and also included a few percent of components such as cyclic hydrocarbons and aromatics. Trade names of these petroleum cuts are Stoddard 'Solvent, Sunoco Spirits, etc. It is to be understood that other hydrocarbon solvents could be employed, such as the aforementioned ingredients in pure condition.
  • Kerosene Suddard Solvent, Sunoco Spirits, etc.
  • the ethers such as diethyl or isopropyl and higher ethers, and dioxane, also have been found useful in many instances.
  • Benzene, toluene and xylene give good results from the chemical standpoint.
  • Esters such as the ethyl acetate, butyl butyrate, and other esters serve as good extracting solvents.
  • a process for the recovery of aromatic amino photographic agents contained in aqueous solutions used in photographic processes which comprises mixing the solution with a solvent for the organic bases essentially consisting of kerosene, separating an extract layer comprising said solvent and the organic base extracted therein from at least a part of the other components, subjecting these extracted materials to a plurality of separation steps wherein the solvent, having the organic base extracted therein, is still further separated from the other materials, drying the resultant extract by contact with a dry-' ing medium, and subjecting the dried extract to intimate contact with a dry acid gas bubbling therethrough to cause the formation of a precipitate comprising at least one of said organic bases and filtering the resultant mixture to obtain the separation of the precipitate from the solvent.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Extraction Or Liquid Replacement (AREA)
US379906A 1941-02-20 1941-02-20 Process for the recovery of organic compounds from photographic solutions Expired - Lifetime US2358053A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
FR962807D FR962807A (enrdf_load_stackoverflow) 1941-02-20
US379906A US2358053A (en) 1941-02-20 1941-02-20 Process for the recovery of organic compounds from photographic solutions
GB7809/41A GB551028A (en) 1941-02-20 1941-06-20 A process for recovering organic bases

Applications Claiming Priority (1)

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US379906A US2358053A (en) 1941-02-20 1941-02-20 Process for the recovery of organic compounds from photographic solutions

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US2358053A true US2358053A (en) 1944-09-12

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FR (1) FR962807A (enrdf_load_stackoverflow)
GB (1) GB551028A (enrdf_load_stackoverflow)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2559896A (en) * 1947-08-22 1951-07-10 Eastman Kodak Co Process for purifying n-methyl-p-aminophenol
US2652428A (en) * 1951-05-05 1953-09-15 Eastman Kodak Co N-alkyl-n-(beta-methylsulfonamidoethyl)-p-aminophenols
US3184021A (en) * 1961-09-14 1965-05-18 Benjamin D Alleman Variable speed device
US4163023A (en) * 1975-12-02 1979-07-31 Fuji Photo Film Co., Ltd. Treatment of photographic processing solutions
JPS54155039A (en) * 1978-05-26 1979-12-06 Chugai Shashin Yakuhin Method of reproducing color photographic bleachhfixing liquid

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2559896A (en) * 1947-08-22 1951-07-10 Eastman Kodak Co Process for purifying n-methyl-p-aminophenol
US2652428A (en) * 1951-05-05 1953-09-15 Eastman Kodak Co N-alkyl-n-(beta-methylsulfonamidoethyl)-p-aminophenols
US3184021A (en) * 1961-09-14 1965-05-18 Benjamin D Alleman Variable speed device
US4163023A (en) * 1975-12-02 1979-07-31 Fuji Photo Film Co., Ltd. Treatment of photographic processing solutions
JPS54155039A (en) * 1978-05-26 1979-12-06 Chugai Shashin Yakuhin Method of reproducing color photographic bleachhfixing liquid

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Publication number Publication date
FR962807A (enrdf_load_stackoverflow) 1950-06-21
GB551028A (en) 1943-02-04

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