US3259498A - Photographic layers suitable for the silver dyestuff bleaching process - Google Patents
Photographic layers suitable for the silver dyestuff bleaching process Download PDFInfo
- Publication number
- US3259498A US3259498A US196432A US19643262A US3259498A US 3259498 A US3259498 A US 3259498A US 196432 A US196432 A US 196432A US 19643262 A US19643262 A US 19643262A US 3259498 A US3259498 A US 3259498A
- Authority
- US
- United States
- Prior art keywords
- formula
- silver
- parts
- bleaching process
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 229910052709 silver Inorganic materials 0.000 title claims description 32
- 239000004332 silver Substances 0.000 title claims description 32
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 21
- 238000004061 bleaching Methods 0.000 title claims description 19
- 230000008569 process Effects 0.000 title claims description 17
- 239000000975 dye Substances 0.000 title claims description 16
- -1 SILVER HALIDE Chemical class 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000002253 acid Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 239000001828 Gelatine Substances 0.000 description 7
- 229920000159 gelatin Polymers 0.000 description 7
- 235000019322 gelatine Nutrition 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229910006069 SO3H Inorganic materials 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- 229940123208 Biguanide Drugs 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
- 229910001626 barium chloride Inorganic materials 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- CHQNGSJEKNJUBX-UHFFFAOYSA-N 1-amino-8-hydroxy-2h-naphthalene-1,2-disulfonic acid Chemical compound C1=CC(O)=C2C(N)(S(O)(=O)=O)C(S(O)(=O)=O)C=CC2=C1 CHQNGSJEKNJUBX-UHFFFAOYSA-N 0.000 description 1
- QLNUJTFSBXIOHA-UHFFFAOYSA-N 1-amino-8-hydroxy-2h-naphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)(S(O)(=O)=O)CC=CC2=C1 QLNUJTFSBXIOHA-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- NZWRKZGKRMQQEC-UHFFFAOYSA-N 3-hydroxynaphthalene-1,2-disulfonic acid Chemical class C1=CC=C2C(S(O)(=O)=O)=C(S(O)(=O)=O)C(O)=CC2=C1 NZWRKZGKRMQQEC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH629261A CH398309A (de) | 1961-05-30 | 1961-05-30 | Photographische Schicht für das Silberfarbbleichverfahren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3259498A true US3259498A (en) | 1966-07-05 |
Family
ID=4307251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US196432A Expired - Lifetime US3259498A (en) | 1961-05-30 | 1962-05-21 | Photographic layers suitable for the silver dyestuff bleaching process |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3259498A (en, 2012) |
| CH (1) | CH398309A (en, 2012) |
| DE (1) | DE1144592B (en, 2012) |
| ES (1) | ES277792A1 (en, 2012) |
| GB (1) | GB939906A (en, 2012) |
| NL (1) | NL279064A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8979987B1 (en) * | 2012-04-06 | 2015-03-17 | Viscot Medical, Llc | Blue dye and methods of manufacture and use thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2304884A (en) * | 1940-04-09 | 1942-12-15 | Eastman Kodak Co | Color photography |
| US2612448A (en) * | 1948-04-02 | 1952-09-30 | Gaspar | Photographic elements containing azo dyes and process using them |
-
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
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2304884A (en) * | 1940-04-09 | 1942-12-15 | Eastman Kodak Co | Color photography |
| FR56699E (fr) * | 1940-04-09 | 1952-10-02 | Kodak Pathe | Procédé de photographie en couleurs |
| US2612448A (en) * | 1948-04-02 | 1952-09-30 | Gaspar | Photographic elements containing azo dyes and process using them |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8979987B1 (en) * | 2012-04-06 | 2015-03-17 | Viscot Medical, Llc | Blue dye and methods of manufacture and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CH398309A (de) | 1966-03-15 |
| DE1144592B (de) | 1963-02-28 |
| NL279064A (en, 2012) | |
| GB939906A (en) | 1963-10-16 |
| ES277792A1 (es) | 1963-01-16 |
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