US3592652A - Photographic silver halide developer compositions and novel developing agents - Google Patents

Photographic silver halide developer compositions and novel developing agents Download PDF

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US3592652A
US3592652A US801138A US3592652DA US3592652A US 3592652 A US3592652 A US 3592652A US 801138 A US801138 A US 801138A US 3592652D A US3592652D A US 3592652DA US 3592652 A US3592652 A US 3592652A
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color
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silver halide
developing agents
photographic
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Charleton C Bard
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Eastman Kodak Co
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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
    • G03C5/30—Developers
    • G03C5/3021—Developers with oxydisable hydroxyl or amine groups linked to an aromatic ring

Definitions

  • This invention relates to photographic silver halide developing agents and photographic developers containing them.
  • Such developing agents can be used in negative or black-and-white developers, but are especially useful in photographic developers adapted for use in color development to produce a colored image record.
  • competing or balancing developing agents can be used to regulate the amount of dye formed, and thereby control the overall color reproduction characteristics of the color photographic material.
  • Two types of competing, or so-called balancing developing agents have been used in color processes, usually reversal color processes wherein the color formers or couplers are in the color developer solution, i.e.:
  • An upper-scale, contrast-modifying and maximum density adjustor which is normally a black-and-white developing agent; examples of this type of balancing developing agent are p-methylaminophenol, l-phenyl-3- pyrazolidone, hydroquinones, and 2,4-di-aminophenol.
  • a toe-chopping developing agent in which the dye maximum density does not change, but the amount of the dye in the minimum density or toe portion of the plot of density against Log. exposure (H and D curve) is reduced.
  • An outstanding example of this type of balancing developing agent is N-benzyl-p-aminophenol (MBAP). This invention is primarily concerned with the latter type of color control.
  • Benzaldehyde a product formed from MBAP reacts with unused p-pheylenediamine color developer to form an oily Schiifs base that tends to produce a tacky dirt in the developer which sticks to the film being processed.
  • Attempts to control the dirt, formed as a result of the oxidation of MBAP, and the hue shift produced by the undesirable coupling of p-aminophenol, have made it necessary to add additional chemicals to the color developer solutions which not only increase the cost of the required materials but also increase the problem of chemical control or balance. Because of this there has been a long sustained search for a better toe-chopping developing agent which will give the desired sensitometric control without producing oxidation products that form dirt and/or color absorbing materials that degrade color quality.
  • Another object of my invention is to provide competing developing agents whose oxidation products not only do not produce unwanted dye, but also do not produce tacky dirt which is characteristic of certain competing developing agents that are presently used on a large scale.
  • Another object is to provide new silver halide developing agents for black-and-white and color photography.
  • phenolic silver halide developing agents containing a monocyclic or bicyclic phenolic group having at least one sulfonamido substituent.
  • the phenolic compound has a monocyclic phenolic group or radical
  • the carbon atoms in the 2- and 4-positions of the monocyclic ring are each connected to a nitrogen atom and one of the nitrogen atoms is the nitrogen atom of a sulfonamido group and the other nitrogen atom is the nitrogen atom of a sulfonamido group or the nitrogen atom of an amino group
  • the phenolic developing agent has a bicyclic phenolic group or radical structure, at least one (usually two) of the carbon atoms in the 2, 4 or 5 positions of the bicyclic ring structure is connected to the nitrogen atom of a sulfonamido group, and the bicyclic phenolic group contains at least one additional N-substi
  • X represents an amino group (including amino group (including amino groups of the class defined by A above) or a sulfonamido group (including a B group as defined above);
  • R and R each represents hydrogen, an alkyl group, substituted or unsubstituted (including, for example, methyl, ethyl, propyl, beta-sulfoethyl, gammasulfobutyl, carboxymethyl, gamma-carboxypropyl, betahydroxyethyl, gamma-hydroxypropyl, gamma-hydroxybutyl, including alkali metal and ammonium salt forms of the alkyl groups containing a sulfo r carboxyl radical), an alkoxy group (e.g., methoxy, ethoxy, propoxyl, etc.), an acyl group (e.g., acetyl, butyryl, benzoy
  • Typical examples of such second silver halide developing agents used in my novel developer compositions are the following:
  • Non-color forming silver halide developing agents i.e., developing agents whose oxidation products do not couple with color-forming couplers including developing 4 agents, such as, a hydroquinone (e.g., hydroquinone, methylhydroquinone, chlorohydroquinone, etc.), a lphenyl-3pyrazolidone (e.g., 1-phenyl-3-pyrazolidone, 4- methyl-l-phenyl-3-pyrazolidone, 4,4-dimethyl-l-phenyl-3- pyrazolidone, etc.), p-methylaminophenol, 2,4-diaminophenol, ascorbic acid, etc.; and
  • a hydroquinone e.g., hydroquinone, methylhydroquinone, chlorohydroquinone, etc.
  • a lphenyl-3pyrazolidone e.g., 1-phenyl-3-pyrazolidone, 4- methyl-l-phenyl-3-
  • Color-forming silver halide developing agents i.e., developing agents whose oxidation products couple with color-forming couplers to form colored images, including the primary aromatic amino color developing agents (e.g., p-phenylenediamine, the alkyl phenylenediamines, the alkyl toluenediamines, etc., which have one primary amino group).
  • the primary aromatic amino color developing agents e.g., p-phenylenediamine, the alkyl phenylenediamines, the alkyl toluenediamines, etc., which have one primary amino group).
  • Developing compositions comprising my phenolic silver halide developing agents and such second non-color forming silver halide developing agent (a) above are advantageously used to make developer solutions that show synergistic effects in black-and-white photography.
  • combinations of 2,4-bis(benzenesulfonamido)phenol with hydroquinone produce a synergistic effect that is illustrated later herein.
  • the developing compositions of my invention can also contain any of the various components that are normally in photographic developing solutions and include materials such as alkalies, alkali metal sulfites, alkali metal bisulfites, alkali metal thiocyanates, alkali metal bromides, alkali metal iodides, thickening agents (e.g., carboxymethyl cellulose, etc.), water softening agents, etc.
  • materials such as alkalies, alkali metal sulfites, alkali metal bisulfites, alkali metal thiocyanates, alkali metal bromides, alkali metal iodides, thickening agents (e.g., carboxymethyl cellulose, etc.), water softening agents, etc.
  • Color-forming couplers are used to advantage in color developer compositions used to prepare a color developer a color film that does not contain incorporated colorforming couplers.
  • Particularly efiicacious compositions for making color developing solutions comprise one of my competing developing agents, a primary aromatic amine color developing agent and a hydroxylamine, e.g., hydroxylaminesulfate, N,N-dimethylhydroxylamine, N,N-diethylhydroxylamine.
  • any of the well-known alkali-soluble coupler compounds can be used to advantage in my color developer solutions. See United States Pat. 3,300,305, issued Jan. 24, 1967 for a summary of such couplers.
  • Useful cyan dye-forming couplers include the alkali-soluble diifusible couplers such as the naphthols, nitronaphthols, hydroxynaphthoic acetamides, acylaminophenols, diacylaminophenols, and others.
  • Magenta dye-forming couplers which are useful in my color developer solutions include the alkali-soluble diffusible couplers such as the pyrazolones, sulfonamide substituted pyrazolones, acylated aminopyrazolones, halogen substituted pyrazolones, coumarones, etc.
  • Yellow dye-forming couplers which are useful in my color developers include the alkali-soluble ditfusible couplers such as the acylacetanilides, sulfonamide-substituted acylacetanilides, etc.
  • My compounds are used to advantage in compositions over a wide range of concentrations.
  • concentrations in the range from about .1 g./l. to about 10 g./l. are used to advantage with a preferred concentration being in the range from about 0.1 to about 2 grams per liter.
  • my competing developing agents do not couple with oxidized color developing agents in the developer solutions to form dyes as do many of the prior art competing developing agents.
  • Another advantage which is provided by use of my competing developing agents is that they do not oxidize to form compounds which produce tacky dirt in the color developer solutions.
  • my balancing developing agents has made it possible to replace the MBAP, and the hydroxylamine (Wholly or partly) that are used in certain commercially used color developing solutions. In certain instances, though, as mentioned before, it may be desired to use hydroxylamine in order to obtain the synergistic effect with my balancing developing agents.
  • My competing developing agents are used to advantage in compositions used for making color developer solutions containing any of the Well-known primary amino silver halide developing agents, such as the p-phenylenediamines including the alkyl phenylenediamines and alkyl toluenediamines. These developing agents are usually used in salt form, such as the hydrochloride or sulfate, which are more stable than the free amine. The p-aminophenols and their substitution products can also be used as color developing agents when the amine group is unsubstituted.
  • p-phenylenediamine developers include substituted p-phenylenediamines, such as the N-alkylsulfonamidoalkyl-p-phenylenediamines, the sulfonamido substituted p-phenylenediamines, etc. All of these color developing agents have an unsubstituted amino group which enables the oxidation product of the developer to couple with the color-forming products to form a dye image. Included among the color developers are, such typical illustrative examples as,
  • Z-amino-S-diethylaminotoluene hydrochloride N-ethyl-beta-methanesulfonamidoethyl-3-methyl-4- aminoaniline sulfate, 4-amino-N,N-diethyl-3-methylaniline hydrochloride, 4 amino-N-ethyl-N-(beta-methanesulfonamidoethyl)-mtoluidine sesquisulfate monohydrate, 3-methyl-p-aminodiethylaniline sulfate, 4-amino-N-ethyl-N-(beta-hydroxyethyl)aniline sulfate, N,N-dimethyl-p-phenylenediamine hydrochloride, etc.
  • the phenolic silver halide developing agents of my invention having sulfonamido substituent(s) are advantageously prepared by reacting the corresponding amino substituted phenolic compound dissolved in a suitable inert organic solvent, such as pyridine, with the appropriately substituted sulfonyl chloride having the formula:
  • My silver halide developing agents which have 2 (or 3) dilferent sulfonamido substituents are advantageously prepared by reacting the appropriate phenolic intermediate having one amino group and one (or two) nitro groups with the appropriately substituted sulfonyl chloride.
  • the intermediate formed is isolated as described, then the nitro group(s) on the intermediate is reduced to the amino group(s) by well-known catalytic hydrogenation reactions (e.g., with hydrogen and Raney nickel), followed by reaction with the appropriately substituted sulfonyl chloride.
  • the final crude product is isolated and purified using the techniques described above.
  • EXAMPLE A Into a 4-neck, 1 liter flask, equipped with mechanical stirrer, condenser, thermometer and well, solid addition port and nitrogen bleed were placed 18.4 g. (0.1 mol.) of 2,4-dinitrophenol, 175 cc. of methanol and 200 cc. (2.3 mol.) of hydrochloric acid. The mixture was steam-heated to a pot temperature of 50 C. and 40 g. (0.715 mol.) of plast iron were added in small amounts at 70-80 C. at which time steam was shut off and iron addition was continued at a rate to maintain a pot temperature between 7080 C. until the entire 5 g. of iron had been added.
  • the pot temperature was adjusted to 20-30 C. and 36 g. (0.204 mol.) of benzenesulfonyl chloride and 35 g. (0.426 mol.) of sodium acetate were added.
  • cc. of acetic acid were added and the mixture was heated with stirring to a pot temperature of 7 0-80" C. for 1 /2 hours. On cooling some product began to separate at 50 C.
  • Water cc. were added and the mixture was cooled to 10l5 C., and 2,4-bis(benzene-su1fonamido) phenol were collected by filtration and washed with two 50 cc. portions of 50 C. Water.
  • the pale lavender solid had a melting point of 193 C.
  • the resulting product was further purified by dissolving it in 100 cc. of methanol, filtering and adding to 300 cc. of water containing 2 g. of sodium dithionite. An odor of sulfur dioxide was present, but the product when collected and washed with water was white and had a melting point of 193 C.
  • the dried, purified product weighed 32 g.
  • EXAMPLE B 4-benzenesulfonamido 2 (p toluenesulfonamido) phenol, Compound 3, was advantageously prepared by reacting one molor equivalent of 2-amino-4-nitrophenol in pyridine with one molor equivalent of p-toulenesulfonyl chloride.
  • the crude product, 2-(p-toluenesulfonamido-4- nitrophenol was isolated, purified, and then reduced to 4- amino--2-(p-toluenesulfonamido)phenol by catalytic hydrogenation.
  • the amino-intermediate was dissolved in pyridine and reacted with an equimolar amount of benzenesulfonyl chloride.
  • Compound 3 was isolated and purified by methods similar to those described in Example A.
  • Compound 5 is prepared like Compound 2 but using an equimolar amount of 2,4-dimino-S-methylphenol in place of 2,4-diaminophenol.
  • EXAMPLE C Compoud 6 was advantageously prepared by reacting one mole of 4-amino-2-nitrophenol dissolved in pyridine with one mole of benzenesulfonyl chloride dissolved in pyridine.
  • the crude 4-benzenesulfonamido-2-nitrophenol formed was separated by pouring the reaction mixture over cracked ice and concentrated HCl acid. After the crude product crystallized, it was separated by filtration, dissolved in alkaline solution, treated with activated carbon, filtered and HCl acid added to make the filtrate acidic to Congo Red paper.
  • the precipitated 4-benzenesulfonamido-2-nitrophenol was then separated by filtration and purified by recrystallization from a suitable solvent such as benzene.
  • Compound 7 is advantageously prepared like Compound 2 by reacting one mole of 2,4-bis(methylamino)- -sulfophenol with two moles of benzenesulfonyl chloride dissolved in pyridine. After completion of the reaction, the reaction mixture is poured over ice and HCl acid, and the product separated and purified by methods similar to those described previously.
  • Compound 8 is advantageously prepared by a method similar to that used for Compound 2 but by reacting one mole of 2,5-diarnino-1-naphthol with two moles of henzenesulfonyl chloride.
  • Compound 9 is advantageously prepared by a method similar to that used to prepare Compound 2 but using phenol (Compound 2). This composition was used to make one liter of a developer solution having the composition:
  • Developers B and C (both outside my invention) were made. Developer B was similar to Developer A but the 2,4-bis(benzenesulfonamido)phenol was omitted. Developer C was similar to Developer A but the hydroquinone was omitted.
  • Three pieces of a conventional camera-speed reversal film containing a gelatino silver bromoiodide emulsion were each given an exposure of 2.3 10 meter candle seconds to a 6l00 K. light source. Each of the three pieces of exposed film, identified as strips 1, 2 and 3, was developed at 70 F.
  • Compound 10 is advantageously prepared by a method similar to that used to make Compound 2 but in which one mole of 2,4-diamino-S-methylphenol is used in place of 2,4-diaminophenol and in which methanesulfonyl chloride is used in place of benzenesulfonyl chloride.
  • Compound 11 is advantageously prepared by a method similar to that used to make Compound 3 but reacting one molar equivalent of 2-amino-4-nitrophenol in pyridine with one molar equivalent of methanesulfonyl chloride, isolation of the 2-methanesulfonamido 4 nitrophenol formed, catalytic hydrogenation of this compound to 2- methanesulfonamido-4-nitrophenol formed, catalytic hydrogenation of this compound to 2-methanesulfonamido- 4-aminophenol followed by reaction of this amino compound with an equimolar amount of benzenesulfonyl chloride.
  • the crude product Compound 11 is isolated and purified by methods similar to those described previously.
  • EXAMPLE 1 A dry composition was made containing 8 grams of hydroquinone and 8 grams of 2,4-bis(benzenesufonamido) The results show that a combination of hydroquinone and 2,4-bis-(benzenesulfonamido)phenol (Developing Agent No. 2) in a conventional developer solution produce 4 times the amount of silver in the film given 93x10- meter candles second exposure that would be expected, based on the amounts of silver developed by a similar developer from which one or the other of the two developing agents was omitted. In the film strips given 2.3x l0 meter candle seconds exposure, the combination developer produced 10 g. of silver/cm. while no detectable silver was developed by a developer containing only one of the two developing agents. These data illustrate the synergistic effect produced when my phenolic developing agents are used with a developing agent (a) identified above for negative development.
  • Example 1 Similar results are obtained when Example 1 is repeated using other of my phenolic silver halide developing agents of Formulas I and II in place of 2,4-bis(benzenesulfonamido)phenol.
  • the useful concentration for my developing agents is in the range of from about 5 to about 20 grams per liter, with a preferred concentration in the range from about 8 to about 15 grams per liter.
  • the other non-color-forming silver halide developing agent (a) in my compositions is advantageously used in the range of from about 1 to 15 grams per liter, and in the preferred range of from about 5 to 10 grams per liter.
  • a composition for preparing a cyan color developing solution comprising 2.05 grams of 4-amino-N- ethyl-N-beta-hydroxyethyl-3-methylaniline sulfate and 2 grams of 2,4-bis-( benzenesulfonamido)phenol.
  • This dry composition was used to make a cyan color developer solution by dissolving it in one liter of a solution containing 1.65 grams of the cyan-forming coupler: 2-(o-acetamido-beta-phenylethyh-l-hydroxynaphthamide; 2 grams of sodium sulfite; 2% grams of sodium bromide and 1 gram of sodium thiocyanate that had been adjusted to a pH of 12.4.
  • the magenta and yellow developers were identical to the magenta and yellow developers of that patent.
  • a suitable color film for such processing is described in Mannes et al. U.S. Pat. 2,252,718, issued Aug. 19, 1941.
  • My phenolic silver halide developing agents are also used advantageously as competing developing agents in color developer solutions that do not contain color-forming couplers and are used for color developing color photographic materials that contain incorporated couplers either in diiferently sensitized silver halide emulsion layers of multilayer materials, or in single layer materials containing three differently sensitized packets that contain the appropriately sensitized silver halide emulsion with the appropriate color-forming couplers.
  • my developing agents are also used advantageously together with a second non-color-forming silver halide developing agent (a) in the negative (black-and-white) developer used in reversal color processes.
  • the optimum concentrations for the developing agents will depend upon the particular developers used, the other components in the developer, and other solutions used in the process, the processing conditions, characteristics of the photographic material to be processed, etc., and are determined by methods will known in the art.
  • the developers of my invention represented by Formulas I and 11 above can also be incorporated in the 10 viscous developing solutions used in color diffusion transfer processes, such as that described in Weyerts et al. U.S. Pat. 3,266,894, issued Aug. 16, 1966.
  • the developers of my invention can be used in whole or in part to replace the hydroquinone-type developer (MPHQ) used in the process of that patent.
  • MPHQ hydroquinone-type developer
  • a photographic silved halide developer composition comprising:
  • X and X each represents a Zz Z1 group or a group, at least one of X and X being a B group having the above formula
  • X represents an amino group or a sulfonamido group
  • R and R each represents hyddogen, an alkyl group, an alkoxy group, an acyl group, halogen, or cyano
  • R R and R each represents hydrogen, an alkyl group or an aryl group
  • Q represents an alkyl group or an aryl group and Z
  • Z and Z each represents hydrogen, an A group as defined above, od a B group as defined above, at least one of the groups Z, Z and Z being a B group as defined above and at least one of Z, Z and Z being a nitrogen-containing group wherein the nitrogen atom is attached directly to the bicyclic ring of II, and
  • said second photographic silver halide developing agent (b) is a primary aromatic amine photographic developing, agent capable of reducing exposed silver halide to produce both metallic silver and oxidation products capable of reacting with a photographic color coupler to provide a colored image record.
  • a photographic silver halide developer composition comprising:
  • a blac-k-and-white silver halide developing agent selected from those having the following formula:
  • X and X each depresents a group or a group, at least one of X and X being a B group having the above formula;
  • X represents an amino group or a sulfonamido group;
  • R and R each represents hydrogen, an alkyl group, an alkoxyl group, an acyl group, halogen, or cyano;
  • R R and R each represents hydrogen, an alkyl group or an aryl group;
  • Q represents an aryl group
  • a primary aromatic amine photographic developing agent capable of reducing exposed silver halide to provide metallic silver and oxidation products capable of reacting with a photographic color coupler to provide a colored image record.
  • a photographic silver halide developer composition comprising:
  • R and R each represents hydrogen, an alkyl group, an alkoxy group, an acyl gdoup, halogen, or cyano;
  • Z, Z and Z each represents hydrogen, a
  • R R and R each represents hydrogen, an alkyl group or an aryl group and Q represents an aryl group, and
  • a primary aromatic amine photographic developing agent capable of reducing exposed silver halide to provide metallic silver and oxidation products capable of reacting with a photographic color coupler to provide a colored image record.
  • a photographic silver halide developer composition comprising:
  • R d R R an R wherein X and X each represents a group or a S OzQ,
  • X represents an amino group or a sulfonamido group
  • R and R each represents hydrogen, an alkyl group, an alkoxyl group, an acyl group, halogen, or cyano
  • R R and R each represents hydrogen, an alkyl group or an aryl group
  • Q represents an alkyl group or an aryl group and Z
  • Z and Z each represents hydrogen, an A group as defined above, or a B group as defined above, said photographic black-and-white silver halide developing agent (a) containing at least two groups having the formula:
  • R and Q each have the definitions given above, and
  • a photographic silver halide developer composition comprising:
  • X and X each represents a ⁇ SO2Q wherein R and Q each have the definitions given above, and (b) a primary aromatic amine photographic develop ing agent capable of reducing exposed silver halide to provide metallic silver and oxidation products capable of reacting with a photographic color coupler to provide a colored image record.
  • a photographic silver halide developer composition comprising:
  • a blac-k-and-white silver halide developing agent selected from those having the following formula:
  • R Z J I 1 Z2 Z1 wherein R and R each represents hydrogen, an alkyl group, an alkoxyl group, an acyl group, halogen, or cyano; Z and Z each represents hydrogen, a
  • R and Q each have the definitions given above, and
  • a primary aromatic amine photographic developing agent capable of reducing exposed silver halide to provide metallic silver and oxidation products capable of reacting with a photographic color coupler to provide a colored image record.
  • a reversal photographic color process comprising black-and-white development of an exposed multilayer photographic color film, followed by at least one reversal re-exposure and color development in a photographic color developer to produce a colored image record, the improvement comprising performing said color development in the presence of a phenolic silver halide developing agent selected from those having one of the formulas:
  • X represents an amino group or a sulfonamido group
  • R and R each represents hydrogen, an alkyl group, an alkoxyl group, an acyl group, halogen, or cyano
  • R R and R each represents hydrogen, an alkyl group or an aryl group
  • Q represents an alkyl group or an aryl group and Z
  • Z and Z each represents hydrogen, an A group as defined above, or a B group as defined above, said photographic silver halide developing agent containing at least two groups having the formula:
  • R and Q each have the definitions given above, at least one of said Q groups being aryl.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US801138A 1967-05-18 1969-02-20 Photographic silver halide developer compositions and novel developing agents Expired - Lifetime US3592652A (en)

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BE (1) BE715270A (en:Method)
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3818078A (en) * 1967-05-18 1974-06-18 Eastman Kodak Co Photographic silver halide developing agents
US4021240A (en) * 1975-12-22 1977-05-03 Eastman Kodak Company Photothermographic and thermographic compositions and uses therefor containing sulfonamidophenol reducing agents and four equivalent color couplers
US4161406A (en) * 1977-12-07 1979-07-17 Philip A. Hunt Chemical Corp. Solution and method for processing high speed video news film

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3818078A (en) * 1967-05-18 1974-06-18 Eastman Kodak Co Photographic silver halide developing agents
US4021240A (en) * 1975-12-22 1977-05-03 Eastman Kodak Company Photothermographic and thermographic compositions and uses therefor containing sulfonamidophenol reducing agents and four equivalent color couplers
US4161406A (en) * 1977-12-07 1979-07-17 Philip A. Hunt Chemical Corp. Solution and method for processing high speed video news film

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FR1565855A (en:Method) 1969-05-02
DE1768498A1 (de) 1971-11-18
GB1235157A (en) 1971-06-09
BE715270A (en:Method) 1968-10-16
DE1768498B2 (de) 1973-02-15
CH489036A (fr) 1970-04-15

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