US3617291A - Two-equivalent couplers for photography - Google Patents

Two-equivalent couplers for photography Download PDF

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US3617291A
US3617291A US674090A US3617291DA US3617291A US 3617291 A US3617291 A US 3617291A US 674090 A US674090 A US 674090A US 3617291D A US3617291D A US 3617291DA US 3617291 A US3617291 A US 3617291A
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coupler
couplers
radical
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benzotriazolyl
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George W Sawdey
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Eastman Kodak Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/22—Naphthotriazoles
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
    • G03C1/8155—Organic compounds therefor
    • 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
    • G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
    • G03C7/30541—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the released group
    • 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
    • G03C7/392—Additives
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/156—Precursor compound
    • Y10S430/158—Development inhibitor releaser, DIR

Definitions

  • ABSTRACT Two-equivalent development inhibitor releasing couplers derived from four-equivalent couplers by replacing a single hydrogen atom on the carbon atom in the reactive coupling position with a benzotriazolyl radical are valuable couplers for use in photographic materials and processes.
  • the immediate couplers including the 2,6biscoupler benzol 1,2- d:4,5-d]bistriazoles absorb ultraviolet light, fluoresce and have good stability to exposure to light, heat, humidity and aldehyde hardening agents, and couple actively to produce good dyes having excellent stability to heat and light,
  • TWO-EQUIVALENT COUPLlElRS FOR PHOTOGRAPHY This invention relates to photography and particularly to a new class of two-equivalent dye-forming couplers and their use in color photography.
  • the color-forming coupler may be either in the developer solution or incorporated in the light-sensitive photographic emulsion layer so that during development it is available in the emulsion layer to react with the color developing agent that is oxidized by silver image development.
  • Diffusible-type couplers are used in color developer solutions.
  • Fischer-type couplers and hydrophobic couplers are incorporated in photographic emulsion layers.
  • couplers are selected which form nondiffusing dyes.
  • the dye image used for image transfer processes should be diffusible but capable of being mordanted or fixed in the receiving sheet. For this purpose a coupler is selected which will produce this type of dye.
  • Conventional color-forming couplers are four-equivalent, that is, they require the development of four molecules of exposed silver halide in order to supply one molecule of oxidized color developing agent that is free to couple and form one molecule of dye.
  • Two-equivalent couplers require the development of only two molecules of exposed silver halide to bring about the formation of one molecule of dye.
  • Twoequivalent couplers are very desirable for color photography, since only one-half the usual amount of silver halide is needed and the light-sensitive coatings can thus be made thinner.
  • Development inhibitor releasing two-equivalent couplers have been described in Whitmore et al., US. Pat. No. 3, l48,062, issued Sept. 8, 1964.
  • Another object of my invention is to provide novel development inhibitor releasing two-equivalent couplers which not only absorb ultraviolet radiation and fluoresce in the blue region of the visible spectrum but which have exceptional resistance to the formation of stain from the effects of light, heat, humidity, and aldehyde hardening agents.
  • Still another object of my invention is to provide a novel class of two-equivalent couplers which not only absorb ultraviolet radiation, fluoresce in the blue region of the visible spectrum and have exceptional resistance to the formation of stain from the effects of heat, light, humidity, and aldehyde hardening agents but which also produce dyes which have excellent stability to exposure to light and heat.
  • the dye-forming coupler moiety of may coupler is advantageously derived from any of the four-equivalent dyeforming couplers well known in the art including the magenta-forming cyanoacetyl coumarone couplers, the S-pyrazolone couplers, etc., the cyan-forming phenolic and naphtholic couplers, and the open-chain yellowforming acylacetonitrile couplers (e.g., alkoylacetonitriles, the aroylacetonitriles, the heterocycloyl acetonitriles, etc.), and the open-chain ketomethylene couplers such as the acylacetyl couplers (e.g., the acylacetanilides, the acylacetamides, etc.).
  • the acylacetyl couplers e.g., the acylacetanilides, the acylacetamides, etc.
  • the acylacetanilide couplers include the alkoylacetanilide couplers, the aroylacetanilide couplers, the pivalylacetanilide couplers, etc.
  • the acylacetamide couplers include the alkoylacctamide couplers, the aroylacetamide couplers, the pivalylacetamide couplers, etc.
  • My novel couplers are characterized by absorbing ul traviolet light, fluorescing in the blue region of the visible spectrum, having good stability to the effects oflight, heat, hu midity and aldehyde hardening agents as well as producing upon color development, dyes having good stability to exposure to light and heat.
  • a and A represent any of the dye-forming coupler moieties derived from prior art four-equivalent couplers linked in their coupling position by a single bond to the benzotriazolyl radical;
  • R and R each represent the same or different member such as hydrogen, halogen (chlorine, bromine, iodine, fluorine), the nitro group, amino, an amido radical (e.g., 2,4-di-t-amylphenoxy acetamido, 2,4-diamylphenoxy butyramido, phenylacetamido, etc.), hydroxyl, an alkoxy radical having from one to four carbon atoms, e.g., methoxy, chloromethoxy, ethoxy, carboxyethoxy, aminoethoxy, butoxy, etc., an alkyl radical having from one to four carbon atoms, e.g., ethyl, methyl, butyl, chloromethyl, trifluoromethyl, omega
  • R and R can represent a phenylazo radical (e.g., phenylazo, methylphenylazo, ethoxyphenylazo, chlorophenylazo, sulfophenylazo, carboxyphenylazo, hydroxyphenylazo, etc.); R and R each represent the same or different member such as hydrogen, halogen (chlorine, bromine, iodine, fluorine), nitro, amino, an amido radical (e.g., 2,4-di-t-amylphenoxy acetamido, 2,4-diamylphenoxy butyramido, phenylacetamido, etc.), hydroxyl, an alkoxy radical having from one to 18 carbon atoms (e.g., methoxy, cyclohexylmethoxy, phenylmethoxy, naphthylmethoxy, tribromomethoxy, Z-aminoethoxy, 3-hydroxypropoxy,
  • R and R can represent a phenylazo radical (e.g., phenylazo, methylphenylazo, octadecylphenylazo, sulfobutylphenylazo, butoxyphenylazo, chlorophenylazo, etc.) and any two adjacent substituents represented by R R R and R can be the nonmetallic atoms necessary to form a 5- to 6-membered ring, such as, a carbocyclic ring (e.g cyclohexanc, cyclopentane, norbornane, benzene, toluene, etc.) or a heterocyclic ring (e.g., morpholine, pyridine, quinoline, piperidine, triazole, etc.
  • a phenylazo radical e.g., phenylazo, methylphenylazo, octadecylphenylazo, sulfobutylphenylazo
  • the preferred yellow dye-forming open-chain couplers of formulas I and ll include couplers in which A and A are represented by the formula:
  • R represents an alkyl group such as an acyclic alkyl group having from one to 32 carbon atoms which may be a normal alkyl radical having from one to 18 carbon atoms, e.g., methyl, propyl, hexyl, octyl, dodecyl, pentadecyl, octadecyl, etc., a secondary alkyl radical in which the secondary carbon atom is attached directly to the carbonyl radical and has attached to it two alkyl radicals each of which may have from one to 18 carbon atoms, as defined above, provided that the R group does not have more than a total of 32 carbon atoms, and includes such groups as l-methylheptadecyl, l-butylheptadecyl, l-decylheptadecyl, l-dodeeylheptadecyl, l-pentadecylhexadecyl,
  • a-Benzotriazolyl-a-cyanoacetylcoumarone a-Benzotriazolyl-4-[a'-(2,4-di-t-amylphcnoxy) butyramido]-cyanoacctylbenzene 4-Benzotriazolyl-3-pentadecyl-l phenyl5- pyrazolonc 4-Bcnzotriazolyl-3-mcthyl-lhenylpyrazolonc d-Bcnzorriazolyl-l-(2 4,6-trichlorophcnyl)-3-[3 a- (ZAdM-amylphcnoxy )aciamido ⁇ bcnzamido]-5- pyrazolonc 4-l5-(4-Anilinophenyl-Z-bcnzotriazolyl)1-3-(4- cyanoanilino)- l 2,4,6 trichlorophcnyl)-5
  • R R R and R are as defined previously, in the presence of pyridine, and preferably also in the presence of a solvent such as, methanol, ethanol, etc., and a buffering agent such as sodium acetate to prepare a compound having the formula:
  • Couplers of formula ll are advantageously made by a similar reaction series in which a diazonium salt having the formula:
  • COUPLER 21 i 4 (2-Benzotriazolyl)-3-pentadecyl-l-phenyl-5-pyrazolone
  • a quantity of 5.2 g. (0.01 mole) of l-phenyl-3-pentadecyl- 4-(2nitrophenylazo)-5-pyrazolone is added to a solution of 400 ml. of ethanol and 25 ml. of a 40 percent aqueous solution of sodium hydroxide contained in a one-liter three-neck flask fitted with a reflux condenser. After the solution is heated nearly to boiling while being stirred, 8 g. (12 equivalents) of zinc dust is added.
  • COUPLER 36 4-( 2-Benzotriazolyl )-N- 8-( 2 ,4-diamylphenoxy)butyl l hydroxynaphthamide
  • a quantity of 6.2 g. (0.01 mole) of 2-[6-(2,4-diamylphenoxy)bytyl]-1-hydroxy-4-(2-nitrophenylazo)naphthamide is suspended in 300 ml. of methanol containing 70 ml. of a 25 percent aqueous solution of sodium hydroxide.
  • the reaction mixture is heated nearly to boiling under a reflux condenser, at which stage 8 g. (12 equivalents) of zinc dust is added.
  • the color of the reaction mixture changes quickly to pale yellow.
  • Coupler 1 By using the procedures described for coupler 36 abenzoyl-a-( 2-nitrophenylazo)-acetanilide is suspended in methanol containing aqueous sodium hydroxide and while heating nearly to boiling under a reflux condenser, zinc dust is added. After the reaction is completed, the excess zinc dust is recovered by filtration and the coupler is precipitated from the filtrate by cooling. The coupler is extracted and recrystallized to give coupler 1 having a melting point of 2l4-2 1 6 C.
  • COUPLER 2 This coupler is prepared by the method described for coupler 1 using a-pivalyl-a-(Z-nitrophenylazo)acetanilide in place of a-benzoyl-a-(2-nitrophenylazo)acetanilide.
  • the purified coupler 2 has a melting point of l6l-162 C.
  • COUPLER 19 This coupler is prepared by a method like that described for coupler 1 using a-(2-nitrophenylazo)-cyanoacetyl coumarone in place of a-benzoyl-a-(2-nitrophenylazo)-acetanilide.
  • the recrystallized coupler 19 has a melting point of 220 3222 C.
  • Coupler 22 is advantageously prepared by heating an aqueous methanol solution containing sodium hydroxide and 3-methyl-1-phenyl-4-(2-nitrophenylazo)'5-pyrazolone while adding zinc dust as described for the preceding couplers. After separating the excess zinc dust, extracting and recrystallizing, coupler 22 having a melting point of 154156 C. is obtained.
  • COUPLER 23 This coupler is obtained as described above using 3-[3-(2,4- di-amyiphenoxy acetamido)benzamido ]-4-(Z-nitrophenylazo)l-(2,4,6-trichlorophenyl)-5-pyrazolone in place of 3- ethyl-N43-hydroxyethylaminoaniline,
  • the recrystallized coupler 23 has a melting point of -l 66 C.
  • the diffusible couplers of my invention are used to advantage in color developer solutions used to color develop light-sensitive elements used for color photography which do not contain a color-forming coupler.
  • any of the well-known primary aromatic amino color-forming silver halide developing agents such as the phenylenediamine, e.g., diethyl-p-phenylenediamine hydrochloride, monomethyl-pphenylenediamine hydrochloride, dimethyl-p-phenylenediamine hydrochloride, 2-amino-5-diethylaminotoluene hydrochloride, 2-amino-5(N-ethylNJauryl)toluene, N-ethylfl-methanesulfonamidoethyl-3-methyl-4-aminoaniline sulfate, Nethyl-3 methanesulfonamidoethyl-4-aminoaniline, 4-N- etc., the paminophenols and their substitution products where the amino group is unsubstituted may be used in the alkaline developer solution with my couplers.
  • Various other materials may be included in the developer solutions depending upon the particular requirements, for example, an alkali metal sulfite, carbonate, bisulfite, bromide, iodide, etc., and the thickening agents used in viscous developer compositions such as are described in Whitmore and Mader U.S. Pat. No. 3,227,550.
  • the following is a typical developer solution given to illustrate but not limit the invention.
  • 2-Amino-S-diethylaminotoluene HCl 2.0 g. Sodium sulfite (anhydrous) 2.0 g. Sodium carbonate (anhydrous) 20.0 g. Potassium bromide 1.0 g. Coupler 2.0 g. Water to 1000.0 ml.
  • the diffusible couplers of my invention are used to advantage in emulsion layers when incorporated by the methods described by Mannes et al. U.S. Pat. No. 2,304,940, issued Dec. 15, 1940.
  • Couplers 4, 6, 10, 29, 32 and 33 illustrate those that are incorporated as Fischer-type couplers.
  • the other nondiffusing couplers are incorporated in emulsion layers by methods such as are described by Mannes et al. U.S. Pat. No. 2,304,939, issued Dec. 15, 1942, Jelley et al. U.S. Pat. No. 2,322,027, issued June 15, 1943, etc., in which highboiling organic solvents are used to dissolve the coupler, and
  • My nondiffusing coupler 4 forms diffusible dye images upon color development and is used to advantage either in image transfer elements or in emulsion layers that contain my coupler as a nonimage-forming competing coupler along with an image-forming coupler.
  • nondifl'using couplers used to illustrate my invention form nondiffusing dyes and are used to advantage in any photographic element where incorporated image-forming couplers are desired.
  • My couplers are used in the color development of photographic hydrophilic colloid-silver halide emulsion layers of the developing-out type either in the color developer solution or in the emulsion layer.
  • the emulsions advantageously contain silver chloride, silver bromide, silver iodide, silver chlorobromide, silver bromoiodide, silver chloroiodide, etc., as the light-sensitive material.
  • Hydrophilic colloids used to advantage include gelatin, col- I loidal albumin, a cellulose derivative, or a synthetic resin, for instance, a polyvinyl compound.
  • Some colloids which are used are polyvinyl alcohol or a hydrolyzed polyvinyl acetate as described in U.S. Pat. No. 2,286,215, of Lowe; a far hydrolyzed cellulose ester, such as cellulose acetate hydrolyzed to an acetyl content of 19-26 percent as described in U.S. Pat. No. 2,327,808 of Lowe and Clark, a water-soluble ethanolamine cellulose acetate as described in U.S. Pat. No.
  • the emulsions used in the photographic element of my invention can be chemically sensitized by any of the accepted procedures.
  • the emulsions can be digested with naturally active gelatin, or sulfur compounds can be added, such as those described in Sheppard U.S. Pat. No. 1,574,994; Sheppard and Punnett U.S. Pat. No. 1,623,499; and Sheppard and Brigham U.S. Pat. No. 2,410,689.
  • the emulsions can also be treated with salts of the noble metals, such as ruthenium, rhodium, palladium, iridium and platinum.
  • the noble metals such as ruthenium, rhodium, palladium, iridium and platinum.
  • Representative compounds are ammonium chloropalladate, potassium chloroplatinate, and sodium chloropalladite, which are used for sensitizing in amounts below that which produces any substantial fog inhibition, as described in Smith and Trivelli U.S. Pat. No. 2,448,060, and as antifoggants in higher amounts, as described in Trivelli and Smith U.S. Pat. No. 2,566,245 and 2,566,263.
  • the emulsions can also be chemically sensitized with gold salts as described in Waller, Collins and Dodd U.S. Pat. No. 2,399,083 or stabilized with gold salts as described in Damschroder U.S. Pat. No. 2,597,856 and Yutzy and Leermakers U.S. Pat. No. 2,597,915.
  • Suitable compounds are potassium chloroaurite, potassium aurithiocyanate, potassium chloroaurate, auric trichloride and 2-aurosulfobenzothiazole methochloride.
  • the emulsions can also be chemically sensitized with reducing agents, such as stannous salts (Carroll U.S. Pat. No. 2,487,850), polyamines, such as diethylene triamine (Lowe and Jones U.S. Pat. No. 2,518,698), polyamines, such as spermine (Lowe and Allen U.S. Pat. No. 2,521,925), or bis(fiaminoethyl)sulfide and its water-soluble salts (Lowe and Jones US. Pat. No.2,52l,926).
  • reducing agents such as stannous salts (Carroll U.S. Pat. No. 2,487,850), polyamines, such as diethylene triamine (Lowe and Jones U.S. Pat. No. 2,518,698), polyamines, such as spermine (Lowe and Allen U.S. Pat. No. 2,521,925), or bis(fiaminoethyl)sulfide and its water-soluble salt
  • the emulsions can also be optically sensitized with cyanine and merocyanine dyes, such as those described in Brooker U.S. Pats. Nos. 1,846,301; 1,846,302; and 1,942,854; White U.S. Pat. No. 1,990,507; Brooker and White U.S. Pats. Nos. 2,112,140; 2,165,338; 2,493,747; and 2,739,964; Brooker and Keyes U.S. Pat. No. 2,493,748; Sprague U.S. Pat. Nos. 2,503,776 and 2,519,001; Heseltine and Brooker U.S. Pat. No. 2,666,761; Heseltine U.S. Pat. No. 2,734,900; VanLare U.S. Pat. No. 2,739,149; and Kodak Limited British Pat. No. 450,958.
  • the emulsions may also contain speed-increasing compounds of the quaternary ammonium type of Carroll U.S. Pat. No. 2,271,623; Carroll and Allen U.S. Pat. No. 2,288,226; and Carroll and Spence U.S. Pat. No. 2,334,864; and the polyethylene glycol type of Carroll and Beach U.S. Pat. No. 2,708,162.
  • Typical supports include cellulose nitrate film, cellulose acetate film, polyvinyl acetal film, polystyrene film, polyethylene terephthalate film,
  • polyethylene film polypropylene film, and related films of resinous materials, as well as paper, glass and others.
  • my emulsions are coated on photographic supports in the form of multilayer color photographic elements wherein at least three differently sensitized emulsion layers are coated over one another on the support.
  • the support is coated in succession with a red-sensitive layer, a green-sensitive layer and a blue-sensitive layer either with or without a Carey Lea filter layer between the blue-sensitive and gree-sensitive layers.
  • the three differently color sensitized layers may be arranged in any other order over one another that is desirable; however, the Carey Lea filter layer obviously would not be put over the blue-sensitive layer.
  • these light-sensitive layers are arranged on the same side of the support.
  • Elements made for image transfer processing may use a separate reception sheet which is contacted with the light-sensitive layer during its development or the reception layer may be an integral part of the light-sensitive element. Any of the support materials mentioned previously may be used for a separate reception sheet.
  • the reception layer comprises a hydrophilic colloid layer containing a cationic mordant, e.g., the polymers of amino guanidine derivatives of vinyl methyl ketone such as described in Minsk U.S. Pat. No. 2,882,156, granted Apr. 14, 1959.
  • Other mordants include the 2-vinyl pyridine polymer metho-p-toluene sulfonate and similar compounds described in Sprague et a1.
  • EXAMPLE 1 Two single-layer bromoiodide silver halide emulsion coatings A and B are made on a cellulose acetate film support.
  • the silver halide emulsions are of the type described by Trivelli and Smith Photo. Journal, 79, 330 (1939). Each coating contains:
  • Coupler A The coupler in Coating A is coupler A, i.e., 3-pentadecyl-1- phenyl-5-pyrazolone (outside the invention) and coating B contains my coupler 21, i.e., 4-benzotriazolyl-3-pentadecyl-lphenyl-5-pyrazolone which is derived from Coupler A. Both coatings are exposed to an intensity scale test object and processed as follows:
  • Coupler No. 21 yields more dye and is more stable to light and heat than its corresponding parent four-equivalent Coupler A.
  • Coating C contains Coupler B, i.e., 4-(2-benzotriazolyloxy)-2-[8-(2,4-diamylphenoxybutyl)] l -hydroxynaphthamide (outside the invention) and Coating D contains Coupler 36 i.e., 4-( 2-benzotriazolyl)-2-[8-(2,4- diamylphenoxybutyUl-l-hydroxynaphthamide.
  • Samples of these coatings are exposed and processed as in example 1, except that instead of the test for printout and yellow they are subjected to a 2-day SANS (simulated average north skylight at 500 foot candles intensity) and a heat fading test (1 week,
  • Coupler 36 according to my invention yields substantially more dye than coupler B, and the dye formed from my coupler is substantially more stable to light and heat than the dye generated from Coupler B.
  • E and F Two single-layer coatings consisting of 78 mg./ft. of coupler and 39 mg /ft. of the coupler solvent tri-cresyl phosphate dispersed in 450 mg./ft. of gelatin are identified as E and F.
  • Coating E contains the coupler B identified above (outside the 'invention) and coating F contains Coupler 36 according to my invention. Both coatings are overcoated with a dilute dispersion of silver bromoiodide grains and gelatin and dried. Coatings E and F are identically exposed to a test object and processed by the procedure described in example 1 except that the pH of the developing solution I is adjusted to 12.0.
  • each processed coating indicates that no dye is formed in the upper layer of coating F (of my invention) and that the lower half of the upper layer of exposed portions of coating E contain distinct clouds of cyan dye formed around the dispersed silver halide grains, indicating a 50 percent wandering rate for the coupler B (outside the invention).
  • EXAMPLE4 A processed sample of each of Coatings A and B of example 1 and coatings C and D of example 2 is viewed while being ililuminated with a fluorescent lamp.
  • the areas of no dye density or minimum dye density in the samples containing the couplers of my invention i.e., B and D
  • Couplers of myinvention absorb substantially more radiation in the region of the electromagnetic spectrum between 300 and 400 m than do the corresponding couplers outside of my invention.
  • My coupler 36 has very markedly different properties from coupler B. For example, my coupler 36 has a melting point of l46-l47 C. compared to 222 C. for coupler B. My coupler 36 in solid form or in solution gives an intense blue fluorescence while coupler B does not fluoresce when exposed to ultraviolet radiation.
  • Coupler 36 couples rapidly to produce a good clean cyan dye while coupler B couples more slowly and produces a somewhat greenish cyan dye. l have found that none of my coupler 36 is or can be made by the method in U.S. Pat. No. 3,148,062 described to make the coupler l have identified as coupler B. Similarly no coupler B is produced by my synthesis of coupler 36.
  • My couplers have the valuable property of resisting attack by aldehyde hardeners used in photographic materials and processes. Undesirable stain formation as well as loss of conventional 5-pyrazolone couplers from attack by aldehydes is avoided by use of my S-pyrazolones.
  • My couplers are used to advantages in photography, particularly in color print materials where the residual incorporated coupler left in highlight areas of processed prints, for example, will fluoresce to brighten these areas in the color print.
  • R is a member selected from the class consisting of a hydrogen, halo, nitro, amino, amido, hydroxyl, alkoxy having from one to four carbon atoms, alkyl having from one to four carbon atoms, the nonmetallic atoms, which taken together with R form a 5- to 6-membered ring, and phenylazo radical;
  • R is a member selected from the class consisting of a hydrogen, halo, nitro, amino, amido, hydroxyl, alkoxy having from one to l8 carbon atoms, alkyl having one -l8 carbon atoms, the nonmetallic atoms which taken together with R, form a 5- to 6-membered ring, the nonmetallic atoms which taken together with R form a 5- to 6-membered ring, and phenylazo radical;
  • R is a member selected from the class consisting of a hydrogen, halo, nitro, amino, amido, hydroxyl, alkoxy having from one to 18 carbon
  • Coupler No l8 replace "111241 4 ,5-d7" with --Ll,2d: l,5-d
  • Coupler No 42 after 4-" insert after “butyramid o/" delete "f"; after “benzotriazolyl” insert Coupler No H7, after “-N-" insert after insert after l-A delete "A and insert --a replace "(2, ldi-t” with ⁇ 2,U-di-tafter "phenyl” insert after "ethyl” insert Coupler No 48, after "butyramidgfi' delete "f" Column 10, line 20, replace “diethyl-p” with diethyl-preplace "monomethyl-p” with -monomethyl-p line 21, replace "dimethyl-p” with "dimeth T- line 26, replace "p-” with --pline 58 after "U.S Pat No 2,80l ,171" insert both-.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
US674090A 1967-10-10 1967-10-10 Two-equivalent couplers for photography Expired - Lifetime US3617291A (en)

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DE (1) DE1800420C3 (de)
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Cited By (53)

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US3770436A (en) * 1970-12-26 1973-11-06 Konishiroku Photo Ind Process for forming cyan image in light-sensitive color photographic material
US3839044A (en) * 1971-03-25 1974-10-01 Eastman Kodak Co Silver halide emulsions containing 2-equivalent color couplers
US3933500A (en) * 1973-03-23 1976-01-20 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US3961963A (en) * 1973-09-13 1976-06-08 Fuji Photo Film Co., Ltd. Multilayer photographic material
US3990899A (en) * 1973-05-04 1976-11-09 Fuji Photo Film Co., Ltd. Multi-layered color photographic light-sensitive material
US4015988A (en) * 1974-03-04 1977-04-05 Fuji Photo Film Co., Ltd. Multilayer color photographic light-sensitive material
USRE29379E (en) * 1973-03-23 1977-08-30 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4046575A (en) * 1973-06-09 1977-09-06 Agfa-Gevaert, Aktiengesellschaft Color photographic material containing 2-equivalent yellow couplers
US4049458A (en) * 1974-06-05 1977-09-20 Agfa-Gevaert, A.G. Photographic silver halide material containing 2-equivalent yellow couplers
US4076533A (en) * 1975-11-10 1978-02-28 Fuji Photo Film Co., Ltd. Silver halide emulsion containing two-equivalent coupler
US4133955A (en) * 1975-10-11 1979-01-09 Agfa-Gevaert Aktiengesellschaft Process for the production of 2-equivalent yellow couplers
US4157919A (en) * 1978-03-31 1979-06-12 Eastman Kodak Company Silver halide emulsions containing yellow-dye-forming couplers
US4170479A (en) * 1975-01-08 1979-10-09 Fuji Photo Film Co., Ltd. Multi-layer color light-sensitive material
US4182630A (en) * 1974-06-26 1980-01-08 Minnesota Mining And Manufacturing Company Pivalyl-acetanilide couplers and photographic elements including them
US4327173A (en) * 1980-01-23 1982-04-27 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4409323A (en) * 1980-02-15 1983-10-11 Konishiroku Photo Industry Co., Ltd. Silver halide photographic material
EP0101621A2 (de) * 1982-08-24 1984-02-29 Fuji Photo Film Co., Ltd. Farbphotographisches Silberhalogenidmaterial
EP0112162A2 (de) 1982-12-13 1984-06-27 Konica Corporation Lichtempfindliches photographisches Silberhalogenidmaterial
US4477563A (en) * 1981-03-16 1984-10-16 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
EP0124795A2 (de) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Photographische Silberhalogenidemulsionen
EP0147854A2 (de) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Lichtempfindliches Silberhalogenidmaterial
JPS61145555A (ja) * 1984-12-19 1986-07-03 Konishiroku Photo Ind Co Ltd 写真感光材料
EP0200502A2 (de) 1985-04-30 1986-11-05 Konica Corporation Lichtempfindliches farbphotographisches Silberhalogenidmaterial
EP0200878A1 (de) 1982-02-24 1986-11-12 Konica Corporation Lichtempfindliches farbphotographisches Silberhalogenidmaterial
EP0228914A2 (de) 1985-12-28 1987-07-15 Konica Corporation Verfahren zur Behandlung eines lichtempfindlichen farbphotographischen Silberhalogenidmaterials
US4743595A (en) * 1984-06-14 1988-05-10 Fuji Photo Film Co., Ltd. Process for preparing 2-amino-5-nitrophenol derivatives
US4774181A (en) * 1987-06-25 1988-09-27 Eastman Kodak Company Imaging element containing fluorescent dye-releasing coupler compound
US4942114A (en) * 1987-04-30 1990-07-17 Fuji Photo Film Co., Ltd. Silver halide photographic materials with reducible brightening agent releaser
US4975359A (en) * 1982-06-11 1990-12-04 Fuji Photo Film Co., Ltd. Photographic light-sensitive materials containing couplers that release diffusible dyes and DIR compounds
US5006452A (en) * 1987-12-17 1991-04-09 Minnesota Mining And Manufacturing Company Silver halide color photographic light-sensitive material
EP0429098A1 (de) 1987-03-09 1991-05-29 Eastman Kodak Company Photographische Silberhalogenidmaterialien und Verfahren das einen Pyrazoloazolekuppler enthält
US5021332A (en) * 1989-06-06 1991-06-04 Agfa Gevaert Aktiengesellschaft Color photographic recording material containing a DIR coupler
US5085979A (en) * 1987-06-25 1992-02-04 Fuji Photo Film Co., Ltd. Silver halide color photographic materials and processing method
US5204232A (en) * 1990-03-15 1993-04-20 Konica Corporation Photographic material with fluorescence compound releaser
EP0572894A2 (de) * 1992-06-03 1993-12-08 Agfa-Gevaert AG Farbfotografisches Aufzeichnungsmaterial mit einem Cyan-DIR-Kuppler
US5332656A (en) * 1992-04-07 1994-07-26 Minnesota Mining And Manufacturing Company Silver halide color photographic light-sensitive material
US5352570A (en) * 1991-06-28 1994-10-04 Eastman Kodak Company Method and photographic material and process comprising a benzotriazole compound
EP0661591A2 (de) 1993-12-29 1995-07-05 Eastman Kodak Company Photographische Elemente die Ultraviolett absorbierendes beladenes Polymerlatex enthalten
US5463072A (en) * 1992-06-03 1995-10-31 Agfa Gevart Ag, D-51368 Process for the preparation of naphtholic 2-equivalent cyan couplers
EP0684511A1 (de) 1994-05-20 1995-11-29 Eastman Kodak Company Niedrigkontrastfilm
EP0686873A1 (de) 1994-06-08 1995-12-13 Eastman Kodak Company Farbphotographisches Element, das neue Epoxy-Abfänger für restlichen Purpurrot-Kuppler enthält
EP0690345A1 (de) 1994-06-23 1996-01-03 Eastman Kodak Company Photographische 2-Äquivalent-Magentaküppler mit aktivitätsverändernden Ballastgruppen
EP0695968A2 (de) 1994-08-01 1996-02-07 Eastman Kodak Company Viskositätsverminderung in einer photographischen Schmelze
EP0773471A2 (de) 1995-11-13 1997-05-14 Eastman Kodak Company Photographisches Element, das eine rotempfindliche Silberhalogenidemulsionsschicht enthält
EP0778493A1 (de) 1995-11-30 1997-06-11 Eastman Kodak Company Aggregierte Farbstoffe für strahlungsempfindliche Elemente
EP0779544A1 (de) 1995-12-11 1997-06-18 Eastman Kodak Company Photographisches Material, das einen verbesserten Pyrazolotriazolkuppler enthält
EP0779543A1 (de) 1995-12-11 1997-06-18 Eastman Kodak Company Photographisches Material, das einen verbesserten Pyrazolotriazolkuppler enthält
EP0837363A2 (de) * 1996-10-17 1998-04-22 Eastman Kodak Company Photographische Elemente enthaltend einen Entwicklungsinhibitor freisetzende Verbindungen
EP0837362A2 (de) * 1996-10-17 1998-04-22 Eastman Kodak Company Silberhalogenidelement enthaltend Triazolinhibitoren
EP1914594A2 (de) 2004-01-30 2008-04-23 FUJIFILM Corporation Farbphotographisches lichtempfindliches Silberhalogenidmaterial und Bilderzeugungsverfahren
CN102030917A (zh) * 2010-11-11 2011-04-27 浙江理工大学 含氮杂环苯并三唑型紫外线吸收剂及其制备方法
WO2013032827A1 (en) 2011-08-31 2013-03-07 Eastman Kodak Company Motion picture films to provide archival images
CN115960064A (zh) * 2023-01-15 2023-04-14 西安交通大学 一种荧光发射材料及有机电致发光器件

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4913576B1 (de) * 1970-12-26 1974-04-01
CA1041345A (en) * 1971-03-20 1978-10-31 Atsuaki Arai Photographic light sensitive element containing yellow color coupler and method for forming yellow photographic images
DE2261361C2 (de) * 1971-12-17 1984-11-29 Konishiroku Photo Industry Co., Ltd., Tokio/Tokyo Farbfotografisches Aufzeichnungsmaterial und Farbentwickler für die Farbfotografie
JPS5120826A (en) * 1974-08-13 1976-02-19 Fuji Photo Film Co Ltd Shashinyokapuraa
CH627562A5 (de) 1977-04-29 1982-01-15 Ciba Geigy Ag Farbphotographisches material.
US4851327A (en) 1986-07-17 1989-07-25 Fuji Photo Film Co., Ltd. Photographic color photosensitive material with two layer reflective support

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US3227551A (en) * 1959-04-06 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US3311476A (en) * 1962-12-26 1967-03-28 Eastman Kodak Co Two-equivalent couplers for color photography
US3369895A (en) * 1960-08-24 1968-02-20 Eastman Kodak Co Two equivalent yellow couplers for color photography

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
US3227551A (en) * 1959-04-06 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US3369895A (en) * 1960-08-24 1968-02-20 Eastman Kodak Co Two equivalent yellow couplers for color photography
US3311476A (en) * 1962-12-26 1967-03-28 Eastman Kodak Co Two-equivalent couplers for color photography

Cited By (61)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3770436A (en) * 1970-12-26 1973-11-06 Konishiroku Photo Ind Process for forming cyan image in light-sensitive color photographic material
US3839044A (en) * 1971-03-25 1974-10-01 Eastman Kodak Co Silver halide emulsions containing 2-equivalent color couplers
USRE29379E (en) * 1973-03-23 1977-08-30 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US3933500A (en) * 1973-03-23 1976-01-20 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US3990899A (en) * 1973-05-04 1976-11-09 Fuji Photo Film Co., Ltd. Multi-layered color photographic light-sensitive material
US4046575A (en) * 1973-06-09 1977-09-06 Agfa-Gevaert, Aktiengesellschaft Color photographic material containing 2-equivalent yellow couplers
US3961963A (en) * 1973-09-13 1976-06-08 Fuji Photo Film Co., Ltd. Multilayer photographic material
US4015988A (en) * 1974-03-04 1977-04-05 Fuji Photo Film Co., Ltd. Multilayer color photographic light-sensitive material
US4049458A (en) * 1974-06-05 1977-09-20 Agfa-Gevaert, A.G. Photographic silver halide material containing 2-equivalent yellow couplers
US4182630A (en) * 1974-06-26 1980-01-08 Minnesota Mining And Manufacturing Company Pivalyl-acetanilide couplers and photographic elements including them
US4170479A (en) * 1975-01-08 1979-10-09 Fuji Photo Film Co., Ltd. Multi-layer color light-sensitive material
US4133955A (en) * 1975-10-11 1979-01-09 Agfa-Gevaert Aktiengesellschaft Process for the production of 2-equivalent yellow couplers
US4076533A (en) * 1975-11-10 1978-02-28 Fuji Photo Film Co., Ltd. Silver halide emulsion containing two-equivalent coupler
US4157919A (en) * 1978-03-31 1979-06-12 Eastman Kodak Company Silver halide emulsions containing yellow-dye-forming couplers
US4327173A (en) * 1980-01-23 1982-04-27 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4409323A (en) * 1980-02-15 1983-10-11 Konishiroku Photo Industry Co., Ltd. Silver halide photographic material
US4477563A (en) * 1981-03-16 1984-10-16 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
EP0200878A1 (de) 1982-02-24 1986-11-12 Konica Corporation Lichtempfindliches farbphotographisches Silberhalogenidmaterial
US4975359A (en) * 1982-06-11 1990-12-04 Fuji Photo Film Co., Ltd. Photographic light-sensitive materials containing couplers that release diffusible dyes and DIR compounds
EP0101621A2 (de) * 1982-08-24 1984-02-29 Fuji Photo Film Co., Ltd. Farbphotographisches Silberhalogenidmaterial
EP0101621B1 (de) * 1982-08-24 1988-06-01 Fuji Photo Film Co., Ltd. Farbphotographisches Silberhalogenidmaterial
EP0112162A2 (de) 1982-12-13 1984-06-27 Konica Corporation Lichtempfindliches photographisches Silberhalogenidmaterial
EP0124795A2 (de) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Photographische Silberhalogenidemulsionen
EP0147854A2 (de) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Lichtempfindliches Silberhalogenidmaterial
US4743595A (en) * 1984-06-14 1988-05-10 Fuji Photo Film Co., Ltd. Process for preparing 2-amino-5-nitrophenol derivatives
JPS61145555A (ja) * 1984-12-19 1986-07-03 Konishiroku Photo Ind Co Ltd 写真感光材料
JPH0549090B2 (de) * 1984-12-19 1993-07-23 Konishiroku Photo Ind
EP0200502A2 (de) 1985-04-30 1986-11-05 Konica Corporation Lichtempfindliches farbphotographisches Silberhalogenidmaterial
EP0228914A2 (de) 1985-12-28 1987-07-15 Konica Corporation Verfahren zur Behandlung eines lichtempfindlichen farbphotographischen Silberhalogenidmaterials
EP0429098A1 (de) 1987-03-09 1991-05-29 Eastman Kodak Company Photographische Silberhalogenidmaterialien und Verfahren das einen Pyrazoloazolekuppler enthält
US4942114A (en) * 1987-04-30 1990-07-17 Fuji Photo Film Co., Ltd. Silver halide photographic materials with reducible brightening agent releaser
US5085979A (en) * 1987-06-25 1992-02-04 Fuji Photo Film Co., Ltd. Silver halide color photographic materials and processing method
US4774181A (en) * 1987-06-25 1988-09-27 Eastman Kodak Company Imaging element containing fluorescent dye-releasing coupler compound
US5006452A (en) * 1987-12-17 1991-04-09 Minnesota Mining And Manufacturing Company Silver halide color photographic light-sensitive material
US5021332A (en) * 1989-06-06 1991-06-04 Agfa Gevaert Aktiengesellschaft Color photographic recording material containing a DIR coupler
US5204232A (en) * 1990-03-15 1993-04-20 Konica Corporation Photographic material with fluorescence compound releaser
US5352570A (en) * 1991-06-28 1994-10-04 Eastman Kodak Company Method and photographic material and process comprising a benzotriazole compound
US5332656A (en) * 1992-04-07 1994-07-26 Minnesota Mining And Manufacturing Company Silver halide color photographic light-sensitive material
EP0572894A2 (de) * 1992-06-03 1993-12-08 Agfa-Gevaert AG Farbfotografisches Aufzeichnungsmaterial mit einem Cyan-DIR-Kuppler
EP0572894A3 (en) * 1992-06-03 1995-09-13 Agfa Gevaert Ag Color photographic recording material with a cyan-dir-coupler
US5463072A (en) * 1992-06-03 1995-10-31 Agfa Gevart Ag, D-51368 Process for the preparation of naphtholic 2-equivalent cyan couplers
EP0661591A2 (de) 1993-12-29 1995-07-05 Eastman Kodak Company Photographische Elemente die Ultraviolett absorbierendes beladenes Polymerlatex enthalten
EP0684511A1 (de) 1994-05-20 1995-11-29 Eastman Kodak Company Niedrigkontrastfilm
EP0686873A1 (de) 1994-06-08 1995-12-13 Eastman Kodak Company Farbphotographisches Element, das neue Epoxy-Abfänger für restlichen Purpurrot-Kuppler enthält
EP0690345A1 (de) 1994-06-23 1996-01-03 Eastman Kodak Company Photographische 2-Äquivalent-Magentaküppler mit aktivitätsverändernden Ballastgruppen
EP0695968A2 (de) 1994-08-01 1996-02-07 Eastman Kodak Company Viskositätsverminderung in einer photographischen Schmelze
EP0773471A2 (de) 1995-11-13 1997-05-14 Eastman Kodak Company Photographisches Element, das eine rotempfindliche Silberhalogenidemulsionsschicht enthält
EP0778493A1 (de) 1995-11-30 1997-06-11 Eastman Kodak Company Aggregierte Farbstoffe für strahlungsempfindliche Elemente
EP0779544A1 (de) 1995-12-11 1997-06-18 Eastman Kodak Company Photographisches Material, das einen verbesserten Pyrazolotriazolkuppler enthält
EP0779543A1 (de) 1995-12-11 1997-06-18 Eastman Kodak Company Photographisches Material, das einen verbesserten Pyrazolotriazolkuppler enthält
EP0837363A2 (de) * 1996-10-17 1998-04-22 Eastman Kodak Company Photographische Elemente enthaltend einen Entwicklungsinhibitor freisetzende Verbindungen
EP0837362A2 (de) * 1996-10-17 1998-04-22 Eastman Kodak Company Silberhalogenidelement enthaltend Triazolinhibitoren
EP0837362A3 (de) * 1996-10-17 1998-12-16 Eastman Kodak Company Silberhalogenidelement enthaltend Triazolinhibitoren
EP0837363A3 (de) * 1996-10-17 1998-12-16 Eastman Kodak Company Photographische Elemente enthaltend einen Entwicklungsinhibitor freisetzende Verbindungen
US6007974A (en) * 1996-10-17 1999-12-28 Eastman Kodak Company Silver halide element containing triazole inhibitors
US6043378A (en) * 1996-10-17 2000-03-28 Eastman Kodak Company Photographic elements containing development inhibitor releasing compounds
EP1914594A2 (de) 2004-01-30 2008-04-23 FUJIFILM Corporation Farbphotographisches lichtempfindliches Silberhalogenidmaterial und Bilderzeugungsverfahren
CN102030917A (zh) * 2010-11-11 2011-04-27 浙江理工大学 含氮杂环苯并三唑型紫外线吸收剂及其制备方法
CN102030917B (zh) * 2010-11-11 2012-10-24 浙江理工大学 含氮杂环苯并三唑型紫外线吸收剂及其制备方法
WO2013032827A1 (en) 2011-08-31 2013-03-07 Eastman Kodak Company Motion picture films to provide archival images
CN115960064A (zh) * 2023-01-15 2023-04-14 西安交通大学 一种荧光发射材料及有机电致发光器件

Also Published As

Publication number Publication date
GB1250318A (de) 1971-10-20
FR1585559A (de) 1970-01-23
DE1800420C3 (de) 1975-04-17
DE1800420B2 (de) 1974-08-29
DE1800420A1 (de) 1969-05-29

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