Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D215/38—Nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D215/38—Nitrogen atoms
  • C07D215/42—Nitrogen atoms attached in position 4
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
  • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
  • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
  • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
  • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
  • C07D235/30—Nitrogen atoms not forming part of a nitro radical
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
  • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
  • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
  • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
  • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D277/18—Nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
  • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D277/38—Nitrogen atoms
  • C07D277/50—Nitrogen atoms bound to hetero atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
  • C07D277/62—Benzothiazoles
  • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
  • C07D277/82—Nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
  • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
  • C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
  • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
  • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
  • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• • 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
  • G03C7/18—Processes for the correction of the colour image in subtractive colour photography

Definitions

• the present invention relates to the production of colored photographic images, more particularly to a process of color correction utilizing an integral masking procedure.
• the cyan dye which should absorb red light and transmit green and blue light usually absorbs a small amount of green and blue light, as well as a major proportion of red light.
• the magenta dye which should absorb green light and transmit blue and red light usually absorbs a considerable amount of blue light and a small amount of red light, as well as a major proportion of green light.
• the yellow dye which should absorb blue light and transmit green and red light is usually satisfactory.
• Correction of the colors on printing is therefor desirable, and this is usually done by masking. Since separate masks are difiicult to register with the color trans parency, it is desirable that the mask be integral with the colored images.
• a color corrected image is formed in a photographic element comprising a silver halide emulsion layer and a color coupler (more particularly a color coupler of the naphthol type) which is reactive with the oxidation product of an aromatic amino developing agent to form by color development a primary dye image which absorbs a major proportion of light in one region of the visible spectrum (more particularly the red light) and undesirably absorbs a minor proportion of light in at least one other region of the visible spectrum (more particularly the green light), by treating the exposed and color-developed photographic element with an oxidizing solution, more particularly a photographic bleaching bath, in the presence of a compound more particularly a 4-amino-pyrazolone-3-compound, which after oxidation couples with the residual color coupler, whereby a secondary dye image having a gradation opposite to that of said primary dye image, and absorbing light in at least one of said unwanted minor absorption regions (more particularly the green light) but transmitting substantially all 3,245,787 Patented Apr.
• a further object is to provide a new method for the preparation of an integral mask in color film, more particularly to provide a yellow colored mask image compensating the unwanted absorption of blue light by the magenta image dye.
• an imagewise exposed photographic element comprising a silver halide emulsion layer and a color coupler which is reactive with the oxidation product of an aromatic amino developing agent to form by color development a primary dye image, after the color forming development, with an oxidizing solution, such as a photographic bleaching bath, in the presence of a compound (called herein.- after mask forming compound) containing a grouping of the following "structure:
• R represents a hydrogen atom or an acetyl group
• R represents a hydrogen atom or a functional substituent which is sufliciently unstable for splitting off during the oxidative coupling, such as e.g. a radical of the formula SOg-X or -COX wherein X represents an hydroxyl radical, an amino radical, a substituted amino radical such as a dialkylamino radical, and an N-morpholinyl radical, a hydrocarbon radical or a substituted hydrocarbon radical, such as an alkyl radical e.g. a methyl radical or a cetyl radical, a substituted alkyl radical such as an aralkyl radical and a chloromethyl radical and a carbocyclic radical, e.g. an aryl radical such as e.-g.
• a radical of the formula SOg-X or -COX wherein X represents an hydroxyl radical, an amino radical, a substituted amino radical such as a dialkylamino radical, and an N-morpholinyl radical, a hydrocarbon radical or a substitute
• a phenyl radical and a substituted aryl radical such as eg a 'p-tolyl radical, a 2,5-dichlorophenyl radical and a 2-decanoylaminophenyl radical, and a heterocyclic radical,
• R represents an alkyl radical such as a methyl radical and an ethyl radical, a substituted alkyl radical such as an aralkyl radical and an alkylene radical forming part of a carbocyclic or heterocyclic ring, an aryl radical, a substituted aryl radical, and a radical of the formula SO X or COX wherein X, represents a hydrocarbon radical such as an alkyl radical, a substituted alkyl radical, and a carbocyclic radical such as an aryl radical, and a heterocyclic radical,
• L and L each represents a methine group or a nitrogen atom, at least one of L and L being a methine group, and
• n is a positive integer from 1 to 2.
• heterocyclic sulphonyl- respectively acyl-hydrazones of the wherein Z represents the non-metallic atoms necessary to complete a heterocyclic nitrogen nucleus such as e.g. a benzothiazole nucleus, a benzoxazole nucleus, a benzimidazole nucleus, a thiazoline nucleus, and a 2- quinoline nucleus, and
• R and R have the value as set further hereinbefore.
• Heterocyclic sulphonyl and acylhydrazones which can be used as mask forming compounds in the process of (13) V the present invention are for instance the compounds the formulae of which are represented as follows:
• heterocyclic alkylsulfonylhydrazone mask comspounds according to this invention can be prepared ezg. thy usirg one of the following methods.
• N-ethy'Fbenzthiwzvlonc-cetylszilfonylhyiirazone 38.6 g. (0.2 mol) of N-ethylbenzthiozolone hydrazone 'prepared according to K. Fuchs, Ber. -.6-1"p. 59 (1928), and 32.4 g. (0.1 mol) of 'cetylsulfonvlchloride are re- '-fiuxed I together for 2"hours with "600 cm? of 'acetonitrile. The formed precipitate of hydrazone hydrochloride is sucked off when still warm, 'vvhereafter the filtrate is cooled. After recrystallization of the resulted crystals 6 from methanol, 39 g. of N-ethyl-benzthiazolone cetyl sulfonylhydrazone are obtained. Melting point: C.
• PREPARATION 2 *N-methyl-quinolone-(Z)-'celylsulf0nylhydraz0ne 2.33 :g. (0.0075 mol) of 1-methy1-2-methylthio-quinovliniurniodide prepared according to O. Fischer, Ber. 35 p. .3677 (1902)., and 2.4 g. (0.0075 mol) of cetylsulfonyl hydrazide are heated for 48 hours at 50 C. with 30 cm. pyridine until the evolution of methylmercaptane has ceased. After pouring out the reaction mixture into wa- :-ter, the obtained solid product is Washed with water and dried and 2 g. of N-methyl-quinolone-(Z)-cetyl sulfonylhydrazone are obtained. Melting point: 101 C. A recrystallization from acetonitrile increases the melting point up to 110 C.
• N,N'-dimethyl-benzimidazolone-celylsulfonylhydrazone 9 g. (0.03 mol) of 1-3-dimethyl-2-methylthiobenzimidazoliniummethylsulfate prepared by S. H'tinig. Ann, 609 p. 107 (1957), and 9.6 g. (0.03 mol) of cetylsul fonylhydrazide are mixed at room temperature With 75 cm. of pyridine. After 48 hours the evolution of methylmercaptane has ceased. The reaction mixture is poured into water, the resulting precipitate is Washed With water, sucked-01f and dried. After recrystallization from methanol 5.3 g. of 'N,N'-dimethyl-benzimidazolone-cetylsulfonyl hydrazone are obtained. Melting point: 113 .C.
• PREPARATION 4 .N-methy l-benzoxazo lone-cety lsulfonylhydrazone 8.3 g. (0.05 mol) of 2-methylthio-benzoxazole preparedaccordingto S. Hiinig Ann., 609, p. 169 (1957), and 9.3 g. (0.05 mol) of p-tolusulfonic acid methylester are heated for 30 min. at 1500 C. After cooling, the reaction product is Washed with ether. 4.2 g. (0.012 mol) of the obtained tolusulfonate are mixed with 3.9 g. (0.012 mol) cetylsulfonylhydrazide dissolved in 50 cm. pyridine.
• N-methyl-thiozolinone-cetylsulf0nylhydraz0ne 1.38 g. (0.005 mol) of 2-methy1thio-3-methyl-thiazolinticianodide and 1.6 g. (0.005 mol) of cetylsulfonylhydraz'ide are mixed and heated for 24 .hours at 50 C. with .15 cm. of pyridine and 1.5 cm. of piperidine. After pouring out into Water, the reaction product is washed withwater and dried. The'hydrazone thus obtained .is recrystallized from methanol. 1.7 g. of N-methyl-thiazolinone-cetylsulfonylhydrazone are obtained. Melting point: 98 C.
• N-ethyl-b enzthiozdlone-(m-decanoylamino phenyl)r sulfonylhydrwzone 3816 g. (0.2 mol) of N-ethyl-benzthiozolonehydrazone :preparedaocording to K. Fuchs, Ber. 61, ,p. 59 (1928),
• the process of color correction of the present invention may be practiced, i.e., by using a color photographic material containing a coupler for magenta belonging to the class of the pyrazolone or indazolone color couplers and/ or a coupler for cyan belonging to the class of the phenol or naphthol color couplers.
• a color photographic material containing a coupler for magenta belonging to the class of the pyrazolone or indazolone color couplers and/ or a coupler for cyan belonging to the class of the phenol or naphthol color couplers.
• yellow to magenta colored mask images are obtained on treating the photographic material with an oxidizing substance such as. present in a ferricyanide bleaching bath.
• the hydrazone mask forming compound is incorporated in one of the layers present in the light-sensitive photographic material, preferably in the silver halide emulsion layer wherein the mask image is to be formed by oxidative coupling of the residual color coupler present in that layer with the mask forming substance; in order to prevent the diffusion of the mask forming compound out of the silver halide emulsion layer wherein this compound originally was incorporated, preferably.
• hetero cyclic sulfonyl or acyl hydrazone mask formingcompounds are used containing a radical (e.g. the radical X and/or X in the above formula) comprising a linear chain of 5 to 20 carbon atoms.
• the color couplers and mask compounds can be incorporated into a photographic silver halide emulsion prepared by means of the colloids usually employed therefor such as for instance gelatin, polyvinyl alcohol, collodion or other natural or synthetic colloids.
• the silver halide emulsion can be cast to a support consisting of paper, glass, nitrocellulose, cellulose esters such as cellulose t-riacetate, polyester, polystyrene or another natural or synthetic resin, and form part of a photographic material 'with one or more emulsion layers.
• the multilayer material usually comprises the following elements: a sup the light-sensitive emulsion layer by a water-permeab1e colloid layer.
• aromatic amino-compounds can 'be used as developers for such material: mono-, diand tria'minoaryl compounds, more especially N,N-dialkyl-p-phenylene- .diamines, such as N,N-diethy1-p-phenylenediamine and N,N-diethyl-2-methyl-p-phenylenediamine, and derivatives into a non-light-sensitive layer which is separated from thereof such .as N,N-dialkyl-N-sulphomethylor carboxymethyl-paphenylenediamine.
• monoaminodevelopers should be citedz: aminophenols and aminocresols or their halogen derivatives and also the aminonaphthols.
• the emulsion obtained is coated on a suitable support and dried. After exposure through a grey wedge witha constant 0.15, the photographic material is developed for 9 minutes at 20 C. in a color developing bath with the following composition:
• This material is rinsed for 30 minutes at 18 to 20 C. and fixed for 5 minutes at-20 C. in a fixing bath of the following composition:
• the material is rinsed again for 10 minutes at 18 to 210 C. and treated for 5 minutes in a bleaching bath of the following composition:
• a mainly magenta colored-image is; obtained together with a yellow dye image, said yellow image being of opposite gradation in respectof theamagenta dye image and reducing the disturbing. influence of the side absorptions' in the formed magenta image.
• emulsion obtained is ready to be coated. After coating this emulsion. forms part of a. multilayer photographic material consisting of the following superposed layers in the indicated sequence: a support, an antihalati'on layer, a gelatin insulating layer, a red-sensitized emulsion layer with color coupler for cyan, a gelatin interlayer, the above-mentioned green-sensitized emulsion layer, a yellow filter layer, a
• blue-sensitive emulsion layer with color coupler for-yellow and at least a gelatin overcoat as antistress layer is included.
• Example 1 After exposure through a grey wedge with a constant 0.15 the photographic material is developed and further treated'as in Example 1.
• a mainly magenta colored image is obtained together with a yellow dye image in the green-sensitized layer, said yellow image being of opposite gradation in respect of the magneta dye image and reducing the distributing influence of the side-absorptions in the formed magenta image.
• R is a member of the group consisting of a hydrogen atom and an acetyl group
• R is a member of the group consisting of an alkyl radical and an aryl radical
• Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing 56 members, at least one of which is a nitrogen atom, and
• X is a member of the group consisting of an hydroxyl radical, an amino radical, an alkyl radical, an aryl radical, and a heterocyclic radical;
• the residual color coupler oxidatively couples with said mask-forming compound to form a secondary dye image having a gradation opposite to that of said magenta primary dye image, said secondary image absorbing light in at least one of said undesirable minor ab- 10' sorption regions but transmitting substantiallyall the. light in said major absorption region.
• said color coupler for magenta is a member of the group consisting oi the pyrazol'one and indazolone' color couplers.
• a color photographic-element useful in the method of claim 1 said element having superposed silver halide emulsionlayers, sensitive, to dilferent regions of the visible spectrum, at least one ofsaid layers containing a-color coupler for magenta which is reactive with the oxidation product of an aromatic amino developing agent; to form by color development a magenta primary d'ye image which absorbs a major proportion of light in one region of the spectrum, and undesirably absorbs a minor proportion'of light in at least one other region of the visible spectrum, such layer also containing a mask'forming compound of the formula:
• R is a lower alkyl radical
• Z represents the non-metallic atoms necessary to complete a heterocyclic nitrogen nucleus
• X is an organic radical comprising a linear chain of 5 to 20 carbon atoms free of ethylenic unsaturation
• said color coupler for magenta also being reactive with the oxidation product of said mask-forming compound to form a secondary dye image having a gradation opposite to that of said magenta primary dye image, and absorbing light in at least one of said unwanted minor absorption regions but transmitting substantially all the light in said major absorption region.
• R is a member of the group consisting of a hydrogen atom and an acetyl group
• R is a member of the group consisting of an alkyl radical and an aryl radical
• Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing 56 members, at least one of which is a nitrogen atom, and X is a memebr of the group consisting of a hydroxyl bath.
• the residual color coupler oxidatively .couples with said masloforming, compound to form a secondary dye imagehaving a gradation opposite to that of said cyan primary dye image, said secondary image absorbing light in at least one of said undesirable minor absorption regions but transmitting substantially all the light in said major absorption region.
• a color photographic element useful in themethod of claim 7, said element having superposed silver halide emulsion layers sensitive to different regions of the visible said layers containing a color 12 R is a lower alkyl radical
• Z represents the non-metallic atoms necessary to complete a heterocyclic nitrog'enLnucleus
• X is an organic radical comprising a linear chainof 5 to 20 carbonatoms free of ethylenic unsaturation
• said color coupler for cyan also being reactive with the oxidation product of said mask-forming compound to form a'secondary dye image having a gradation opposite to that of said cyan primary dye image, and absorbing light in at least one of said unwanted minor absorption regions but transmitting substantially all the light in said major absorption region.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Plural Heterocyclic Compounds (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)
• Quinoline Compounds (AREA)
• Indole Compounds (AREA)
• Photoreceptors In Electrophotography (AREA)
• Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

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• 0
  • FR FR79706D patent/FR79706E/fr not_active Expired
  • NL NL263254D patent/NL263254A/xx unknown
  • NL NL295656D patent/NL295656A/xx unknown
  • BE BE634930D patent/BE634930A/xx unknown
  • BE BE602250D patent/BE602250A/xx unknown
• 1960
  • 1960-11-14 DE DEG30927A patent/DE1300019B/de active Pending
  • 1960-11-14 US US71117A patent/US3245787A/en not_active Expired - Lifetime
• 1961
  • 1961-04-03 US US100010A patent/US3245788A/en not_active Expired - Lifetime
  • 1961-04-06 DE DEG31993A patent/DE1297470B/de active Pending
• 1962
  • 1962-07-30 GB GB29127/62A patent/GB993749A/en not_active Expired
• 1963
  • 1963-06-24 CH CH778163A patent/CH428435A/fr unknown
  • 1963-07-30 DE DE1447678A patent/DE1447678C3/de not_active Expired

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