US2220908A - Production of colored photographic images by color development - Google Patents
Production of colored photographic images by color development Download PDFInfo
- Publication number
- US2220908A US2220908A US265999A US26599939A US2220908A US 2220908 A US2220908 A US 2220908A US 265999 A US265999 A US 265999A US 26599939 A US26599939 A US 26599939A US 2220908 A US2220908 A US 2220908A
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- US
- United States
- Prior art keywords
- color
- acyl
- image
- silver
- photographic images
- Prior art date
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- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 silver halide Chemical class 0.000 description 25
- 229910052709 silver Inorganic materials 0.000 description 17
- 239000004332 silver Substances 0.000 description 17
- 239000000839 emulsion Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 235000013350 formula milk Nutrition 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- OKVRHGVPCKGTOC-UHFFFAOYSA-N 1-(1-hydroxynaphthalen-2-yl)-2-methylpropan-1-one Chemical compound C1=CC=CC2=C(O)C(C(=O)C(C)C)=CC=C21 OKVRHGVPCKGTOC-UHFFFAOYSA-N 0.000 description 1
- JBGJVMVWYWUVOW-UHFFFAOYSA-N 1-(1-hydroxynaphthalen-2-yl)ethanone Chemical compound C1=CC=CC2=C(O)C(C(=O)C)=CC=C21 JBGJVMVWYWUVOW-UHFFFAOYSA-N 0.000 description 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- SKIBELYSXFYZPS-UHFFFAOYSA-N 4-n-ethylbenzene-1,4-diamine Chemical compound CCNC1=CC=C(N)C=C1 SKIBELYSXFYZPS-UHFFFAOYSA-N 0.000 description 1
- VVYWUQOTMZEJRJ-UHFFFAOYSA-N 4-n-methylbenzene-1,4-diamine Chemical compound CNC1=CC=C(N)C=C1 VVYWUQOTMZEJRJ-UHFFFAOYSA-N 0.000 description 1
- 102000007469 Actins Human genes 0.000 description 1
- 108010085238 Actins Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101100460719 Mus musculus Noto gene Proteins 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 101100187345 Xenopus laevis noto gene Proteins 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/34—Couplers containing phenols
- G03C7/344—Naphtholic couplers
Definitions
- rnonuc'rlou or cononsn rn'o'rocnarn- 10 moms BY conon DEVELOPMENT JohnDavid Kendalland Ronald Bernard Collins,
- the invention relates to the production of a colored photographic images by color develop- ,ment.
- a colored image may be formed 5 simultaneously with the silver image obtained by developing an exposed silver halide.
- emulsion if a substance known as a "color former is employed, for example, if the color former is mixed with-the developer or incorporated in the emulll) sion.
- the colored image may be revealed by bleaching out the silver image with, for example, farmers reducer or another known photographic bleaching agent.
- a further object of the invention is to provide a method of producing colored photographic images with the aid of such color formers and a still further object is to provide light sensitive silver halide photogo graphic materials containing the new color formers.
- a process for the 5 production or colored photographic images comprises developing a reducible silver salt image with an aromatic amino compound as the developer in the presence of a color former which is a 2-acyl1-l-naphthol in which .the 2 substituent consists of a carboxylic acyl group and in which the total substituents on the naphthalene nucleus contain between them at least three carbon atoms.
- the i-position in the naphthalene nucleus may be unsubstituted or may be substituted by a halogen atom.
- the acyl group may be represented by the formula R-C0-, and R in this formula may be any hydrocarbon or substituted hydrocarbon radlcle.
- B may be an alkyl group (preferably containing up to six carbon atoms) a substituted alkyl group, an-aryl group, e. g. a phenyl or naphthyl group, a substituted aryl group, an" aralkyl group, a g. a benzyl group, ora substituted aralkyl group.
- Substituents in the alkyl, aryl, or aralkyl group may be, for example, chlorine or bromine atoms or nitro,hydrox y, alkoxy, amino and substituted amino groups, the substituted alkyl, aryl, or aralkyl groups being preferably linked by one of their carbon atoms to the caro rl roup. 1
- the new color formers are compounds ,of the following general formula:
- R represents an alkyl group, preferably containing up to six carbon atoms, a substituted alkyl group, an aryl group, a substituted .aryl
- Z represents a hydrogen atom or a halogen atom and the various X's, which may be the same 'or different, represent hydrogen atoms, halogen atoms or any monovalent substituent groups, e. g.
- alkyl aryl, aralkyl, amino, substituted amino, hy-
- the compound 2 acetyl 1 naphthol which since it does not contain 3 carbon atoms in substituent groups is not included in the present invention, is ,also capable of actin as a color former.
- this compound is very sensitive to the presence of sulphites such as are com monly included in developers to inhibit aerial oxidation.
- the color formers included in the present invention have, in general, a satisfactory, resistance to the action of ,sulphites and may be employed in conjunction with developers contaming sulphites.
- the developers used for developing colored photographic images with the aid of the color formers of the present invention do not, of course, necessarilyv contain sulphlte, and where the risk of oxidation of the developenis not a material factor, sulph-ites may be omitted;
- 2-acyl-1- naphthols which contain no other substituent (i. e. where Z and all the Xs ofvthe above formula are hydrogen atoms and R contains at least two carbon atoms) are very suitable; examples are 2-acyl-1-naph thnls in which the acyl groups are the following: n-propionyl, n-butyryl, iso-butyryl, n-valeryl, isovaleryl, trimethylacetyl, caproyl, and heli yl, oenanthoyl, pelarg'onyl, lauryl, myristyl, palmityl, stearyl, benzoyl, phenylacetyl, phenylpropionyl and cinnamoyl.
- the 2-acyl-l-naphthols may contain positions of X and Z in the above general formula.
- a very satisfactory color-former of the type where Z is an halogen atom is 2-propionyl-4-brom-l-naphol. 1 i
- the color formers may be of the time wherein one or more of the X's in the above for mula are monovalent substituent groups, e; g.- zzfi-di-acetyl 1 zfi-dihydroxy naphthalene and 2:6- di-n-butyryl 1:5-dihydroxynaphthalene.
- aoylnaphthols in which two naphthol residues are 'link edbytheresidueofadlbasicacidsuohasgo sucoinic acid or adipic acid.
- An example oi type is 2:2'-succinoyl-1:1'-dinaphthol.
- Suitable aromatic amino compounds which g may be employed as the developers in conjunction with the color-formers or this invention are H derivatives oip-phenylene-diamine and particularly the asymmetric dialkyl p-phenylenedi- V amines, e. g. p-aminodimethylaniline, p-aminodiethylaniline and p-aminodihutylaniline.
- developing agents which may 'be used include p-phenylenediamine itseli', p-methylaminoaniline, p-ethylaminoaniline and p-aminophenol," N.N diethyl o-phenylenediami-ne, phenylenediamine, 1,2,5 toluylenediamine,
- noto'luene and its dihydrochloride and a-y-dldiamine.
- aromatic amino-developing agents may beused hydroxypropyl pphenylene in the form or their salts, which may be either inorganic or organic.
- the salts are in general more stable than the tree bases.
- the color formers may bemixed with the degraphic emulsions:
- a specific example of a suitable developing solution is as follows: Dsvmormo SoLunon-A niethyl-p phenylene die hydrochloarm 1 Sodium carbonate crystals,
- a 25 its function being to fortify the solution against developers containing these compounds give dye.
- photoi image was iormedin association with the silver
- Example 2 Fifty cos. of a melted photographic emulsion containing essentially silver chloride in the proportion of gms. of silver halide per kilogram of emulsion were mixed with a previously prepared mixture of cos. of a 10% gelatin solution and 20 cos. of a 1% ethyl alcohol solution oi 2-iso-butyryl-1-naphthol. This emulsion was then coated upon paper and test pieces of the coated paper were exposed under a test negative and developed for 2 minutes at 65 F. in developing solution-A but using equivalent ethyl alcohol in place of .thepcolur-iormer solution.
- the product When a polybasic acid is employed it is possible that the product will consist wholly or partly of-a compound in which there is more than one naphthol nucleus. The use of such products is included within the process of the present invention.
- the process of development employing the color-formers in accordance with the present invention maybe applied either toga latent image in an emulsion of a silver halide which has been exposed 'to' the action of light, for example, in, a camera or behind a photographic negative image ⁇ or it may be applied to the residual unaltered silver halide left when an initial reduced silver image has been dissolved away as in the reversal process of development; or it may be applied to a developed photographic image in metallic silver which has been fixed by the removal of unaltered silver halide by means of solvents and subsequently converted to a developable silver salt by means of known photographic bleaching agents.
- the residual silver halide and the silver salt respectivelyma'y be made developable by the action of light or in any other way, 9. g. by treatment with sodium arsenite.
- the method which comprises developing a photographic element containing a reducible silver salt image with an aromatic amino developing compound in the presence of an acyl naphthol comprising twonaphthol radicals linked by the diacyl radical of an aliphatic dibasic carhoxylic acid.
- a photographic developer solution compris- 4.
- A' method as set forth in claim fl whe'rein ing an aromatic amino developing compound and i the acyl naphthol is 2:2'-adipcyl-1:1'-dinaphan acyl naphthol comprisins two naphthol radi- '5 thol.
- a light sensitive silver halide photographic dibasic carboxylic acid. v emulsion containins as a color iormer an acyl 9.
- a photographic developer solution comprising two naphthol radicals ing an aromatic amino developing compound and 0 linked by the diacyl radical of an aliphatic di- 2:2'-succinoyl-l1'-dinaphthol. 10
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
Patented Nov.'12, 1940 I,
rnonuc'rlou or cononsn rn'o'rocnarn- 10 moms BY conon DEVELOPMENT JohnDavid Kendalland Ronald Bernard Collins,
Ilford, England,
assignors to Ilford Limit, 11-
ford, Essex, England, a. British company No Drawing, Application April 4, 1939, Serial no.
265,999. In Great 10 Claims.
The invention relates to the production of a colored photographic images by color develop- ,ment.
It is known that a colored image may be formed 5 simultaneously with the silver image obtained by developing an exposed silver halide. emulsion if a substance known as a "color former is employed, for example, if the color former is mixed with-the developer or incorporated in the emulll) sion. The colored image may be revealed by bleaching out the silver image with, for example, Farmers reducer or another known photographic bleaching agent.
It is an object of t s invention to provide a is new range of color formers. A further object of the invention is to provide a method of producing colored photographic images with the aid of such color formers and a still further object is to provide light sensitive silver halide photogo graphic materials containing the new color formers.
Other objects of the invention will appear hereinafter.
According to the invention a process for the 5 production or colored photographic images comprises developing a reducible silver salt image with an aromatic amino compound as the developer in the presence of a color former which is a 2-acyl1-l-naphthol in which .the 2 substituent consists of a carboxylic acyl group and in which the total substituents on the naphthalene nucleus contain between them at least three carbon atoms. The i-position in the naphthalene nucleus may be unsubstituted or may be substituted by a halogen atom.
The acyl group may be represented by the formula R-C0-, and R in this formula may be any hydrocarbon or substituted hydrocarbon radlcle. Thus B may be an alkyl group (preferably containing up to six carbon atoms) a substituted alkyl group, an-aryl group, e. g. a phenyl or naphthyl group, a substituted aryl group, an" aralkyl group, a g. a benzyl group, ora substituted aralkyl group. Substituents in the alkyl, aryl, or aralkyl group may be, for example, chlorine or bromine atoms or nitro,hydrox y, alkoxy, amino and substituted amino groups, the substituted alkyl, aryl, or aralkyl groups being preferably linked by one of their carbon atoms to the caro rl roup. 1
The new color formers, therefore, are compounds ,of the following general formula:
group, an aralkyl group or substituent groups in the Britain April 4, 1938 I in which R represents an alkyl group, preferably containing up to six carbon atoms, a substituted alkyl group, an aryl group, a substituted .aryl
a substituted aralkyl group linked by a carbon atom to the carbonyl group, Z represents a hydrogen atom or a halogen atom and the various X's, which may be the same 'or different, represent hydrogen atoms, halogen atoms or any monovalent substituent groups, e. g.
alkyl, aryl, aralkyl, amino, substituted amino, hy-
droxy, alkoxy, nitro, sulphonic ,acid or acyl groups, the group C0--R and one of the X's contaming .between them ,at least three carbon atoms. k
The compound 2 acetyl 1 naphthol, which since it does not contain 3 carbon atoms in substituent groups is not included in the present invention, is ,also capable of actin as a color former. However, this compound is very sensitive to the presence of sulphites such as are com monly included in developers to inhibit aerial oxidation. The color formers included in the present invention have, in general, a satisfactory, resistance to the action of ,sulphites and may be employed in conjunction with developers contaming sulphites. v
The developers used for developing colored photographic images with the aid of the color formers of the present invention do not, of course, necessarilyv contain sulphlte, and where the risk of oxidation of the developenis not a material factor, sulph-ites may be omitted;
As indicated above, awide range of 2-acyl-1- naphthols is included in the present invention. Thus, for example, simple 2-acyl-l-naphthols which contain no other substituent (i. e. where Z and all the Xs ofvthe above formula are hydrogen atoms and R contains at least two carbon atoms) are very suitable; examples are 2-acyl-1-naph thnls in which the acyl groups are the following: n-propionyl, n-butyryl, iso-butyryl, n-valeryl, isovaleryl, trimethylacetyl, caproyl, and heli yl, oenanthoyl, pelarg'onyl, lauryl, myristyl, palmityl, stearyl, benzoyl, phenylacetyl, phenylpropionyl and cinnamoyl. Again, the 2-acyl-l-naphthols may contain positions of X and Z in the above general formula. Thus, a very satisfactory color-former of the type where Z is an halogen atom is 2-propionyl-4-brom-l-naphol. 1 i
Again, the color formers may be of the time wherein one or more of the X's in the above for mula are monovalent substituent groups, e; g.- zzfi-di-acetyl 1 zfi-dihydroxy naphthalene and 2:6- di-n-butyryl 1:5-dihydroxynaphthalene.
Also included in the present invention are aoylnaphthols in which two naphthol residues are 'link edbytheresidueofadlbasicacidsuohasgo sucoinic acid or adipic acid.- An example oi type is 2:2'-succinoyl-1:1'-dinaphthol.
Suitable aromatic amino compounds which g may be employed as the developers in conjunction with the color-formers or this invention are H derivatives oip-phenylene-diamine and particularly the asymmetric dialkyl p-phenylenedi- V amines, e. g. p-aminodimethylaniline, p-aminodiethylaniline and p-aminodihutylaniline. Other developing agents which may 'be used include p-phenylenediamine itseli', p-methylaminoaniline, p-ethylaminoaniline and p-aminophenol," N.N diethyl o-phenylenediami-ne, phenylenediamine, 1,2,5 toluylenediamine,
noto'luene, and its dihydrochloride and a-y-dldiamine. These aromatic amino-developing agents may beused hydroxypropyl pphenylene in the form or their salts, which may be either inorganic or organic. The salts are in general more stable than the tree bases.
of the hydrochlorides, sulfates and acetates.
' The color formers may bemixed with the degraphic emulsions:
veloper, or incorporated in the emulsion. A specific example of a suitable developing solution is as follows: Dsvmormo SoLunon-A niethyl-p phenylene die hydrochloarm 1 Sodium carbonate crystals,
- NazCOaIOI-IsO gms Sodium sulphite crystals, NazSOs'lHsO" a 125, Color former (1% or a saturated'solution at room temperature in alcohol, whichever is the weaker) cc s 100 Distilled water to make litre 1 If desired, the sodium sulphite may be omitted,
A 25 its function being to fortify the solution against developers containing these compounds give dye.
images in varying shades of blue and blue-green and these dye images remain inthe gelatin layer after removal of the silver image by treatment with, for example, ers reducer.
In. tests carried'out with such developing solutions the time of development was two minutes at 65 F. but in many cases there were indica tions to show that this time was more than sumcient to produce the dye image required.
The following specific examples illustrate the use of the color formers as additions to seamize 2 Fifty cos. of a melted photographic emulsion containing essentially silver bromide in the proportion ofio gms. oi silver halide per kilogram were mixed with e. previously prepared mixture of 25 cos. of'a 10% gelatin solution and 25 cos. of-
al%' ethyl alcohol solution of 2-pmpionyl lnaphthol, and the emulsion was coated on paper in'the usual way. Test pieces of this coated paper were then exposed under a standard test negative and then developed for two minutes at 65 F. in .the'above developing solution-A but.
using equivalent ethyl alcohol in place of the color former solution, when a lame-green dyechloro pexamples of suitable salts mention is made mospheric pressure.
photoi image was iormedin association with the silver Example 2 Fifty cos. of a melted photographic emulsion containing essentially silver chloride in the proportion of gms. of silver halide per kilogram of emulsion were mixed with a previously prepared mixture of cos. of a 10% gelatin solution and 20 cos. of a 1% ethyl alcohol solution oi 2-iso-butyryl-1-naphthol. This emulsion was then coated upon paper and test pieces of the coated paper were exposed under a test negative and developed for 2 minutes at 65 F. in developing solution-A but using equivalent ethyl alcohol in place of .thepcolur-iormer solution.
A deep blue-green dye-image was produced in association with the silver image and the dyeimage remained in the gelatin layer after removal of the silver image by treatment with Farmers reducer. I
- Instead of the specific color-formers named in V the 2-position with an organic acid or organic acid anhydride in the presence of zinc chloride at a temperature between 160 and 200 C. at at-;
When a polybasic acid is employed it is possible that the product will consist wholly or partly of-a compound in which there is more than one naphthol nucleus. The use of such products is included within the process of the present invention.
v The process of development employing the color-formers in accordance with the present invention maybe applied either toga latent image in an emulsion of a silver halide which has been exposed 'to' the action of light, for example, in, a camera or behind a photographic negative image} or it may be applied to the residual unaltered silver halide left when an initial reduced silver image has been dissolved away as in the reversal process of development; or it may be applied to a developed photographic image in metallic silver which has been fixed by the removal of unaltered silver halide by means of solvents and subsequently converted to a developable silver salt by means of known photographic bleaching agents. In the'last two'cases, the residual silver halide and the silver salt respectivelyma'y be made developable by the action of light or in any other way, 9. g. by treatment with sodium arsenite.
We claim:
. 1. The method which comprises developing a photographic element containing a reducible silver salt image with an aromatic amino developing compound in the presence of an acyl naphthol comprising twonaphthol radicals linked by the diacyl radical of an aliphatic dibasic carhoxylic acid. r
2,22o ,ooa v 3 I I 8. A method as set iorth'in claim2 wherein the acyl naphthol is 2:2'-adipoyl-1:l'-dinaphthe acyl naphthol is 2:2'-succinoyl-1:l'-dinaphthol.
thol I 8. A photographic developer solution compris- 4. A' method as set forth in claim fl whe'rein ing an aromatic amino developing compound and i the acyl naphthol is 2:2'-adipcyl-1:1'-dinaphan acyl naphthol comprisins two naphthol radi- '5 thol. cals linked by the diacyl radicaloi an aliphatic 5. A light sensitive silver halide photographic dibasic carboxylic acid. v emulsion containins as a color iormer an acyl 9. A photographic developer solution comprisnaphthcl, comprising two naphthol radicals ing an aromatic amino developing compound and 0 linked by the diacyl radical of an aliphatic di- 2:2'-succinoyl-l1'-dinaphthol. 10
basic carboxylic acid. 10. A photographic developer solution com- ,6. An emulsion as set forth in claim 5 wherein prising an aromatic amino developing compound the acyl naphthol is 2:2'-succinoy1-1:1-dinaphand 2:2'-adipoyl-.l-l'-dlnaphthol. thOL' 1 JOHN DAVID KENDALL.
5 3!. An emulsion as set forth in claim 5 wherein nomm 3mm com. 6
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2220908X | 1938-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2220908A true US2220908A (en) | 1940-11-12 |
Family
ID=10901558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US265999A Expired - Lifetime US2220908A (en) | 1938-04-04 | 1939-04-04 | Production of colored photographic images by color development |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2220908A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2441491A (en) * | 1944-05-12 | 1948-05-11 | Ilford Ltd | Cyanacetylamino phenol color formers for color photography |
| US4284714A (en) * | 1979-05-09 | 1981-08-18 | Fuji Photo Film Co., Ltd. | Method of forming a photographic image |
| WO2018132609A1 (en) | 2017-01-11 | 2018-07-19 | Invidi Technologies Corporation | Cloud-based decisioning for addressable asset system |
-
1939
- 1939-04-04 US US265999A patent/US2220908A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2441491A (en) * | 1944-05-12 | 1948-05-11 | Ilford Ltd | Cyanacetylamino phenol color formers for color photography |
| US4284714A (en) * | 1979-05-09 | 1981-08-18 | Fuji Photo Film Co., Ltd. | Method of forming a photographic image |
| WO2018132609A1 (en) | 2017-01-11 | 2018-07-19 | Invidi Technologies Corporation | Cloud-based decisioning for addressable asset system |
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