Classifications

• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
  • G03C7/28—Silver dye bleach processes; Materials therefor; Preparing or processing such materials
  • G03C7/29—Azo dyes therefor
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B43/00—Preparation of azo dyes from other azo compounds
  • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B43/00—Preparation of azo dyes from other azo compounds
  • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
  • C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
  • C09B43/145—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with polycarboxylic acids

Definitions

• R represents a ben- PHOTOGRAPHIC M i i ALS FOR THE SILVER zene or a naphthalene residue containing at least two DYEST FF BLEA HIN P OCESS sulphonic acid groups
• the residue R or R may be a benzene residue sub- 15,506/64 stituted by two sulphonic acid groups and which contains US Cl 96 99 G03c 1/10 6 Claims at most an alkyl group, for example, a methyl group as 10 a further substituent.
• the said residue may also be a naphthalene residue substituted by two sulphonic acid ABSTRACT OF THE DISCLOSURE groups and which does not contain further substituents.
• R or R is a benzene residue it may contam as substituents, for example, one or two alkyl groups or a hydroxyalkoxy group, an alkoxy group or an acylamino group, and no further substituents in addition to the two last-mentioned groups, or an alkyl group. All these substituents advantageously contain not more than four carbon atoms.
• N N SIOlH
• N N NH 0C@ CO HN
• N N Y Y SOaH H038 in which R and R each represents a benzene or a naphin which X and Y have the meanings given above.
• aminoazo dyestuffs being obtained by coupling a diazos i l dyestugs of h formula tized aminobenzene sulphonic acid or aminonaphthalene disulphonic acid with an aminobenzene or aminonaph- (2)
• the dyestuffs of the Formula 1 may be present in multipreferably the dichloride, of an azobenzeneor azothiolayer material containing on a support a red-sensitized phene-dicarboxylic acid of the formula layer dyed with a cyan dyestuif, a green-sensitized layer (7) dyed with a magenta dyestutf and, finally, a blue'sen- 5 sitized layer dyed with a dyestuif of the Formula 1.
• the d e tutfs of the Formula 1 are generally very R and R in the Formula 1 and the Formula 7 are monoresistant to difiusion in the usual kinds of layer. They cyclic and thus contain a single benzene ring without any display no tendency to change into an opalescent or dull further Tings Connected therewith, either p y y form in the gelatine layers during drying and storage, anellation.
• the film is exposed behind a step-Wedge and the silver Couplmg compcnems image is developed in a 1methylamino-4-hydroxybenzenesulphate hydroquinone developer and fixed.
• fi ig' or i i g g g or 3 The image dyestutf is then bleached out depending on g y l g or oxy s i E g 40 the amount of silver present, in a bath containing 30 to roxyel jgf i l g i 100 parts by volume of 32% hydrochloric acid, 40 to 120 me y enzene ace y a mo m parts of potassium bromide, 30 to parts of thiourea phenylurea, 1-ammobenzene-w-methanesulphonic ester, 1- d 0001 t 0 01 t f 2 3 h d h n amino-Z- or 3-ethoxy benzene, l-amin
• a yellow image which is the inverse of the silver Dicarboxylic acids wedge is obtained which is bleached pure white at the 50 areas where the silver was present in the greatest density.
• AZobenzene-3,3'-dicarboxylic acid A yellow image of this kind can also form part of multi- 4,4-dimethylazobenzene-3,3-dicarboxylic acid, colour photographic material; in this case, the amounts of 4,4-dichloroazobenzene-3,3'-dicarboxylic acid, gelatine are adapted to suit the required thickness of the azobenzene-4,4'dicarboxylic acid, layers.
• the dyestuif of the Formula 8 may be prepared as 2,2-dimethoxyazobenzene-5,5-dicarboxylic acid, follows: 2,2'-dichlor0azobenzene-5,5'-dicarboxylic acid, 60.6 parts of Z-aminonaphthalene-l,8-disulphonic acid, 2,2-dimethylazobenzene-4,4-dicarboxylic acid, in the form of the sodium salt, are dissolved in 1,000 parts 3,3-dichloroazobenzene-4,4'-dicarboxylic acid, of water, the solution is cooled with ice to 0 C., and 4,4'-dichloroazobenzene-5,5'-dicarboxylic acid, diazotized in the usual manner with parts of 37% hy- 2,2'-aZothiophene-5,5'-dicarboxylic acid.
• the dyestuifs of the Formulae 1 to 5 can be prepared 60 to C. in 300 parts of water and 30 parts of 37% by known methods. Coupling to form the aminomonoazo hydrochloric acid, the solution is cooled with ice to 5' dyestuffs is carried out in an acid medium. 5 C. and added to the solution of the diazo compound.
• the Amines diflicult to couple may be coupled in the form batch is stirred for 24 hours at a temperature of 8 to 15 of their w-methanesulphonic acids, with subsequent elim- C.
• the aminobuffering the mineral acid with sodium acetate The acidic azo dyestuffs are advantageously reacted with the dicarsuspension of the monoazo dyestufi is heated to 65 C. boxylic acid halide containing azo groups in the presence 70 and is then filtered at 30 C. of an agent capable of binding acid.
• the photographic layers containing, in acdissolved in 150 parts of water and then 5.2 parts of socordance with the invention, at least one dyestuff of the dium borate are added to the solution at room tempera- Formula 1 may also be prepared by known methods and lure.
• the reaction mixture is stirred for 12 to 14 hours at room temperature and is then heated to 60 C. and kept at that temperature for one hour.
• the trisazo dyestufi so formed is precipitated by the addition of 300 parts by volume of ethanol and 100 parts by volume of 7 N potassium acetate and is then isolated by suction filtration. Purification is effected by dissolving the dyestuff in 200 parts of Water, precipitating it by the addition of 50 parts by volume of ethanol and 100 parts by volume of 7 N potassium acetate, and again isolating it by suction filtration. After drying, about 4 parts of dyestufi are obtained.
• the azobenzene-4,4-dicarboxylic acid dichloride can be prepared in the following manner:
• the reaction mixture is then discharged into 10,000 parts of hot water whereby the azobenzene dicarboxylic acid dissolves.
• 25 parts of sodium hypochlorite solution containing 13 to 14% of active chlorine are added to the filtrate.
• 320 parts by volume of glacial acetic acid are added and the dicarboxylic acid precipitates.
• the batch is suction filtered and the filter cake is washed with 500 parts of 1% acetic acid and with 500 parts of water.
• the residue is dried in vacuo and 74 parts of azobenzene-4,4'-dicarboxylic acid are obtained in the form of a pink powder.
• any one of the dyestuffs II to XIX obtainable from the components listed in the following table may be incorporated in a gelatine layer in the manner indicated instead of the dyestuff of the Formula 8.
• These dyestuffs can be prepared in a manner analogous to that used for the dyestulf of the Formula 8.
• the gelatine layers may contain additives, for example,
• the material is manufactured in a manner such of film, 0.5 gram of dyestuif and a quantity of silver bromide corresponding to 1 to 1.2 grams of silver.
• the film so prepared is exposed to red, green and blue light beneath a coloured diapositive.
• the reproduction is then developed in the following manner:
• Photographic material as claimed in claim 1 in which the layer contains silver halide and a dyestuff of which is fast to light and otherwise permanent is obtained. 5 the formula HOaS HOS
• R represents a radical selected from the group 15 consisting of benzene and thiophene
• X represents a member selected from the group consisting of a hydrogen atom, an alkyl group, and an alkoxy group
• Y represents a member selected from the group consisting of a hydrogen atom and an alkyl group
• m and 11 each represents an integer of at the most 2.
• Y represents a member selected from the group consisting of a hydrogen atom and an alkyl group.
• Photographic material as claimed in claim 4 in which the layer contains silver halide and a dyestuff of the formula SOaH HOrS
• X represents a member selected from the group the formula in which R represents a radical selected from the group consisting of benzene and naphthalene containing at least two sulfonic acid groups, R represents a radical selected Hots oona HaC-O S 0311 References Cited UNITED STATES PATENTS 6/1942 Chechak 96-99 I. TRAVIS BROWN, Primary Examiner.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)
• Paper (AREA)

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Cited By (5)

Citations (1)

• 1964
  • 1964-12-02 CH CH1550664A patent/CH448739A/de unknown
• 1965
  • 1965-11-15 DE DE1472811A patent/DE1472811C3/de not_active Expired
  • 1965-11-25 GB GB50158/65A patent/GB1094956A/en not_active Expired
  • 1965-11-29 BE BE673012A patent/BE673012A/xx unknown
  • 1965-11-30 US US510672A patent/US3443953A/en not_active Expired - Lifetime
  • 1965-12-01 AT AT1082365A patent/AT260691B/de active
  • 1965-12-01 ES ES0320264A patent/ES320264A1/es not_active Expired
  • 1965-12-01 NL NL656515630A patent/NL148164B/xx not_active IP Right Cessation

Patent Citations (1)

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