Classifications

• • 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
  • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
  • C09B35/02—Disazo dyes
  • C09B35/039—Disazo dyes characterised by the tetrazo component
  • C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
  • C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
  • C09B35/16—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from hydroxy-amines
• • 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
  • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling

Definitions

• Dyestufis of this kind also exist among the ordinary commercial direct dyestufis, for example, the disazo-dyestulfs that are obtained by coupling tetrazotized 3 3'-dirnethoxy 4: 4'-diamino-l: l-diphenyl on both sides with 1-amino-8-hydroxynaphthalene-3:6- or -2:4-disulfonic acid. To a large extent these dyestufls meet the above requirements.
• the present invention is based on the observation that dyestuffs obtained from a tetrazotized 3:6:3:6'-tetraalkoxy-4:4-diaminodiphenyl and l-amino 8 hydroxynaphthalene disulfonic acids do not exhibit the above disadvantage in the silver dyestuff bleaching process.
• the invention therefore provides photographic layers 3,Z5 ,43 Patented July 5, 1966 suitable for the silver dyestuff bleaching process which contain a dyestufi of the general formula in which R and. R each represent the radical of a 1- amino-8 hydroxy-naphthalene sulfonic acid, bound to the azo linkage in a position vicinal to the hydroxyl group, and at least one of the said radicals contains two sulfonic acid groups, and in which X and X represent an alkyl group which may by interrupted by an ether bridge.
• the dyestuffs of the Formula 1 can be obtained by coupling a tetrazo-compound of a diamine of the formula X1-O l )Xz (in which X and X have the meanings given above) to from a hydrazo-compound of the formula (')X1 Xr-O X2(
• the compounds of the Formulae 2, 3 and 4 contain alkyl groups which are bound to the benzene nuclei through an oxygen atom and which may themselves be interrupted by an oxygen atom, that is to say, an ether bridge. Two different or identical groups of that kind may be bound to a single benzene nucleus.
• the groups X and X advantageously contain at most 5 carbon atoms.
• -.-OX and/ or OX there may be mentioned n-butoxy, n-propoxy, isopropoxyand B-methoxy-ethoxy (OCI -I CH O-.CH groups but more especially ethoxy and methoxy groups.
• coupling components for making the disazodyestuffs of the Formula 1 there are used 'l-amino-8-hydroxy naphthalene sulfonic acids.
• the tetrazo-compounds of the diarnines of the Formula2 are coupled on at least one side with a 1amino-8-hydroxynaphthalene disulfonic acid, and they may be coupled on the other side with a l-amino- S-hydroxynaphthalene monosulfonic acid, such as 1- amino-S-hydroxynapthalene-4-sulfonic acid.
• the amino group in the 1-position may be a primary amino group or, especially in the case of the 3 :6- and the 4:6-disulfonic acid, a substituted amino group, for example, a monoalkylamino or dialkyl amino group, such as a monoor di-methylprocess, or they can be rendered completely fast to difamino, monoor di-ethylamino, a hydroxyalkylamino products of dicyandiamidine with form-aldehyde.
• a substituted amino group for example, a monoalkylamino or dialkyl amino group, such as a monoor di-methylprocess, or they can be rendered completely fast to difamino, monoor di-ethylamino, a hydroxyalkylamino products of dicyandiamidine with form-aldehyde.
• Angroup such as p-hydroxyethylamino, or phenylamino fusion with suitable agents, such as biguanide or reaction group or especially an acylamino group, such as an acetylother method of enhancing the fastness to diffusion conamino or propionylamino group.
• suitable agents such as biguanide or reaction group or especially an acylamino group, such as an acetylother method of enhancing the fastness to diffusion conamino or propionylamino group.
• suitable agents such as biguanide or reaction group or especially an acylamino group, such as an acetylother method of enhancing the fastness to diffusion conamino or propionylamino group.
• suitable agents such as biguanide or reaction group or especially an acylamino group, such as an acetylother method of enhancing the fastness to diffusion conamino or propionylamino group.
• the fastness to light of the finished blue component NH OCCBH4OCCGH5) color image can be substantially improved by treatment or toluene-sulfonylamino group. with an agent yielding nickel or more especially with an As stated above, asymmetrical diazo-dyestuffs can be agent yielding copper, and this causes no appreciable obtained by coupling in stages with two difl'erent 1- change in shade.
• the dyestufl of the formula 3) EN (
• the fastness to light of the blue image is the symmetrical diazo-dyestuifs are preferred, inter alia, substantially improved by after-treatment with a copper because they are simpler to make.
• the dyestuffs of the Formula 1 can be made by the Processing is then carried out as follows: usual known methods.
• a tetrazo-compound of a diamine (l) Hardening for 5 minutes in an aqueous formaldeof the Formula 2 is coupled with the 1-amino-8-hydroxyhyde solution of 4% strength. naphthalene sulfonic acid or acids in an alkaline medium.
• Potassium bromide and gr of Z iH l The dyestutfs exhibit absorption maxima at 610 to 640 Washing in Water for 5 minutesmu, and they have low subsidiary color densities.
• the fastness to light of the image so obtained can be substantially improved by treating it for 5 to 10 minutes in a copper sulfate bath for 2 to 5% strength, or in a copper acetate bath of 2 to 4% strength, and then washing it for 5 to 10 minutes in water and drying it.
• the dyestufl of the Formula 11 is obtained by first running the aforesaid tetrazo-compound into a solution of 32 parts of 1-amino-8- hydroxynaphthalene-2:4-disulfonic acid and 100 parts of sodium bicarbonate in 800 parts of Water, and, after the formation of the diazo-azo-compound, adding a solution of 32 parts of 1-amino-8-hydroxynaphthalene-4:6-disulfonic acid and parts of anhydrous sodium carbonate in 400 parts of water. After 2 hours the dyestuff is precipitated in the manner described above.
• the dyestuff of the Formula 8 can be prepared as follows:
• 30.4 parts of 3:6:3:6'-tetramethoxy-4:4-diamino-1:1- diphenyl are stirred in 500 parts of Water with 26 parts of hydrochloric acid of 30% strength, and dissolved, if necessary, by heating to C. After the addition of a further 26 parts of hydrochloric acid, the temperature is lowered to 0 C. by the addition of ice. 14 parts of sodium nitrite, dissolved in 50 parts of water, are added in portions over a period of 10 minutes. There is formed a clear yellow solution of the tetrazo-compound.
• the solution so obtained is run into a solution of the coupling component, which has been prepared by dissolving parts of 1- amino-S-hydroxynaphthalene-2:4-disulfonic acid and parts of anhydrous sodium carbonate in 800 parts of water, and cooling the solution to 0 to 2 C. by the addition of ice. Coupling takes place rapidly. After 2 to 4 hours, the reaction mixture is heated to 65 C., and the dyestuff is precipitated by the addition of 250 to 400 parts
• Example 2 200 grams of silver bromide emulsion are sensitized with a red sensitizer, and mixed at 35 C.
• Example 3 The procedure is the same as in Example 2, with the exception that 0.28 gram of barium chloride is added, instead of the condensation product of dicyandiamidine.
• Stabilizers, spreading agents, such as saponin, and/or hardening agents may be incorporated with the casting solutions described in Examples 2 and 3 before they are cast.
• Example 4 3 grams of the dyestutf of the formula 7 8 are dissolved in 500 ml. of water, and the solution is bleaching process which contains silver halide and a disazoadded to 1' liter of a red-sensitized silver bromide gelatine dyestufI of the formula which contains, per liter, 30 to 35 grams of silver.
• the dyestulf-gelatine emulsion so 0Xz Xvi) obtained is cast on a suitable support, if desired, as one of in which R and R each represents the radical of a 1- the layers of a three-color multi-layer material, and procamino-8-hydroxynaphthalene disulfonic acid which is essing is carried out as described in Example 1.
• the devel- 10 bound to the azo linkage in 7-position, and X and X each oped and after coppered l layer possesses a hi h degree represents a member selected from the group consisting of of fasmess to light an alkyl group and an alkoxyalkyl group.
• the dyestuff of the Formula 13 can be made as follows: A P p c layer i l for the silver dyestuff 53.6 parts of 3 6:3z6 tetra-e-ethoxy-ethoxy-4:4-dibleaching process which contains silver halide and a disazoamino-1:1'-diphenyl are stirred for several hours in 600 15 dyestufi of the formula parts of Water in the presence of 26 parts of hydrochloric H3C O ONO acid of 30% strength.
• a photographic layer suitable for the silver dyestuff What 1s claimed is: bleaching process which contains silver halide and the 1.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
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• Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)

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Citations (2)

• 0
  • NL NL279064D patent/NL279064A/xx unknown
• 1961
  • 1961-05-30 CH CH629261A patent/CH398309A/de unknown
• 1962
  • 1962-05-21 US US196432A patent/US3259498A/en not_active Expired - Lifetime
  • 1962-05-22 GB GB19709/62A patent/GB939906A/en not_active Expired
  • 1962-05-29 DE DEC27123A patent/DE1144592B/de active Pending
  • 1962-05-29 ES ES277792A patent/ES277792A1/es not_active Expired

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