US2480815A - 2-naphthyl j-acid and the urethanes thereof as color formers - Google Patents
2-naphthyl j-acid and the urethanes thereof as color formers Download PDFInfo
- Publication number
- US2480815A US2480815A US25534A US2553448A US2480815A US 2480815 A US2480815 A US 2480815A US 25534 A US25534 A US 25534A US 2553448 A US2553448 A US 2553448A US 2480815 A US2480815 A US 2480815A
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- US
- United States
- Prior art keywords
- acid
- parts
- naphthyl
- urethanes
- emulsion
- Prior art date
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- Expired - Lifetime
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- 150000003673 urethanes Chemical class 0.000 title description 19
- 239000002253 acid Substances 0.000 title description 14
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 title description 4
- 239000000839 emulsion Substances 0.000 description 29
- -1 silver halide Chemical class 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 16
- 239000000975 dye Substances 0.000 description 15
- 229910052709 silver Inorganic materials 0.000 description 12
- 239000004332 silver Substances 0.000 description 12
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000003222 pyridines Chemical class 0.000 description 4
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 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 2
- BQBKYSPXQYHTIP-UHFFFAOYSA-N ethyl n-butylcarbamate Chemical compound CCCCNC(=O)OCC BQBKYSPXQYHTIP-UHFFFAOYSA-N 0.000 description 2
- RMWSIPOCOLVAQW-UHFFFAOYSA-N ethyl n-dodecylcarbamate Chemical compound CCCCCCCCCCCCNC(=O)OCC RMWSIPOCOLVAQW-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 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 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000004060 quinone imines Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 229940001584 sodium metabisulfite Drugs 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 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 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- MBJAPGAZEWPEFB-UHFFFAOYSA-N 5-amino-2-(4-amino-2-sulfophenyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C1=CC=C(N)C=C1S(O)(=O)=O MBJAPGAZEWPEFB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- VRVVZKNTLCDQKY-UHFFFAOYSA-N ethyl n-hexadecylcarbamate Chemical compound CCCCCCCCCCCCCCCCNC(=O)OCC VRVVZKNTLCDQKY-UHFFFAOYSA-N 0.000 description 1
- ZQRKKRPGMWJFCH-UHFFFAOYSA-N ethyl n-octadecylcarbamate Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)OCC ZQRKKRPGMWJFCH-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960005382 phenolphthalein Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000000715 transmission low energy electron diffraction Methods 0.000 description 1
- 238000000411 transmission spectrum Methods 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
- the present invention relates to color photogand more particularly to the preparation :of dye images in a photographic element "while rutilizin'g in either the photographic emulsion or the developer 2- nap'hthy'l J-acid -'or a urethane thereof.
- J acid and its derivatives-are widely employed as dye intermediates, particularly .in the prepa- :ration of azo dyes.
- J acid has the following iiormula:
- theN-phenyl and acyl derivatives are characfteiiz'd theiact that they are capable (if -profinding deeply colored dyes or high tinctorial strength. Because of this pro erty and their "ability to form Iquinoneimih'e dyes, these compounds would normally recommend "themselves for use in color photography as 'colorffoimers.
- .It is accordingly :an object of the present invention to utilize Q-naphthyl J-acid and the urethanes thereof in the iformation of :colorimages in -col'or photography.
- *A' zfurther object of the present invention is to provide :a photographic silver halide emulsion with :color lformers which are urethanes of 2-- naph-thyl J -acid and which are non-difiusingin the emulsion.
- the urethanes when employing the urethanes, it is preferable to use them in the silver halide emulsion rather than in the developer. When so used, it is imperative that the urethanes do not migrate from the emulsion layer in which they are located. In this connec tion it is to be observed that the urethanes possess a nuclear hydroxyl group and asa consequence yield dyes of the cyan type upon conventional color development. This in turn means that in compounding color formers with the urethanes, the urethanes must be located in the red sensitive layer. 1
- R is an aliphatic chain of at least 12 carbon atoms such as dodecyl, lauryl, tetradecyl, hexadecyl, octadecyl, palmityl and the like.
- Z-naphthyl J-acid is produced by heating Z-naphthylamine, sodium meta-bisulfite and J-acid, preferably while adding the J-acid portionwise to the reaction mixture.
- the 2-naphthy1 J-acid thus obtained is converted into the urethanes by treating the same with the desired alkyl chlorocarbonate at low temperatures, preferably ranging from about 5 to 15 C. Desirably the reactants are vigorously agitated during the reaction. The desired low temperature is maintained by external cooling.
- an acid binding agent should be present and this may be either an inorganic acid binding agent such as sodium hydroxide, potassium hydroxide, sodium acetate and the like, or an organic binding agent such as pyridine, quinoline or the like.
- an inorganic acid binding agent is used, and particularly if a low molecular weight chloroformate is employed, the reaction is effected in an aqueous medium.
- a high molecular chloroformate it is preferable to work with an organic acid binding agent in an organic solvent such as dimethyl formamide.
- the urethanes containing a long aliphatic chain preferably one having at least 12 carbon atoms
- they are dispersed in a photographic silver halide emulsion.
- one gram of the urethane is dissolved in 7 cc. of ethyl alcohol.
- the solution is then diluted with distilled water, neutralized-with sodium hydroxide and added to the emulsion. This procedure is followed in the subsequent examples.
- Dye images are produced from the involved w 4 color formers by development with a conventional primary amine developer while using the color formers in non-difiusing form in a photographic emulsion or in diffusing form in said conventional developers.
- Example 1 Into a suitable vessel equipped with a rapid stirring apparatus, a refluxing condenser, and a heating element are placed 525 parts of 2- naphthylamine, 1400 parts of hot water and 665 parts of sodium metabisulfite. The mixture is heated to boiling and refluxed for 15 minutes. 100 parts of J -acid (the inner salt of commerce) .are introduced and the mixture is refluxed for 2 hours. Another 100 parts of J-acid are introduced and the mixture'is again refluxed for 2 hours. The addition-is repeated in the above fashion until a total of 500 parts of J -acid have been introduced. The resultant suspension is then refiuxedovernight. The hot mixture is filtered, taking on as much of the liquid as possible. The'wet press cake is returned to the vessel and extracted at 60-80" C. with a mixture of 2,000 parts water'and 500 parts 30% sodium chloride solution. The insoluble solid is collected by filtration and pressed as dry as possible.
- J -acid the inner salt of commerce
- the press cake is returned to the vessel and titurated with a mixture consisting of 3,000 parts of water and 2,000 parts of toluene at 7080 C.
- the phases are separated.
- the aqueous phase is reextracted with 1,000 parts of toluene and is then diluted to a total of 6,000 parts.
- Sodium chloride solution 1,000 parts of 30% is added and the clear liquid is neutralized with acetic acid and diluted to a total volume of 8,000 parts.
- the precipitate which separates on standing and cooling, is collected by filtration and washed with a little ice water.
- the wet press cake is dissolved in 8,000 parts of boiling water and decolorized with activated charcoal.
- the filtrate is treated with 200 parts of concentrated hydrochloric acid while being maintained at the boiling point.
- the resulting suspension is kept hot for one-half hour and is then filtered.
- the solid so obtained is washed with water until the wash water no longer runs soapy and is then dried. This is crude 2- naphthyl J-acid.
- the crude Z-naphthyl J-acid obtained above is suspended in 2,000 parts of boiling glacial acetic acid and 800 parts of USP pyridine are added.
- the resulting hot solution is maintained at -100 C. for a period of 1 to 2 hours during which time the. crystalline pyridine salt of 2- naphthyl J-acid separates as a pale. yellow solid. .
- the material is collected by filtration, washed with acetic acid, and dried. If desired, the pyridine salt may be reconverted to the free acid by solution in sodium hydroxide and the addition of hydrochloric acid. There is obtained in the above manner a yield of 240 parts of pure dry pyridine salt of 2-naphthyl J-acid.
- An exposed photographic silver bromide emulsion is developed in a conventional color forming developer containing about 1 gram of the 2- an'd'th'en' treated" with'iapart's; of ethylchlorof" carbonate.
- ethyl urethane of2-naphthyFJ-acid. brilliant dye image is obtained upon working up the developed emulsion.
- Example 3 The procedure is the same as in Example 2 excepting that the ethyl chloroformate is replaced by butyl chloroformate and the resulting butyl urethane of Z-naphthyl J -acid is employed in the developer in place of the ethyl urethane of 2-naphthyl J-acid.
- Example 4 Into a suitable vessel equipped with a water separator and an agitator are placed 360 parts of dry dimethylformamide and 360 parts of dry benzene. The mixture is refluxed for a period of 2 to 5 hours, until no more water is obtained in the water separator. The mixture is then distilled until 1'70 parts of distillate have been obtained. 75 parts of the pure dry pyridine salt of 2-naphthyl J-acid (obtained in Example 1) is introduced and the mixture is heated with stirring until complete solution has taken place. The vessel is now equipped with a thermometer and means for the slow introduction of liquids and the content is cooled to 6 C. 2-hexadecylchloroformate (75 parts) is cautiously introduced, maintaining the temperature below 10 C.
- pyridine 55 parts is slowly added with good agitation, maintaining the temperature below 10 C.
- the resulting dark brownish red solution is stirred at 5 to 10 C. for a period of 2 hours.
- the temperature is then raised to 18-25 C. and the mixture is stirred for 16 to 24 hours.
- the resulting suspension is evaporated to dryness with the aid of a good vacuum.
- the residue is extracted with 750 parts of dry benzene.
- the insoluble material is removed by filtration and discarded.
- the clear benzene filtrate is evaporated at 100 C. and 22 mm. pressure.
- the residue is dissolved in 1,000 parts of hot glacial acetic acid and the solution is cooled to 25 C.
- the insoluble waxy material which separates at this point is removed by filtration and discarded.
- Lithium carbonate 50 parts is added, and the mixture is stirred ffor one-half ness.
- the residue consists of the lithium salt of the 2-hexadecyl urethane 0f Z-naphthyl J -acid.
- the color formers for the production of quinoneimine dyestufif images in the color forming development method, they may also be employed to produce azo dyestuff images by the silver dye bleaching method.
- the film After exposure, the film is developed in a black and White developer and is then bathed for a few minutes in a solution containing the tetrazo compound of benzidine-2.2'-disulfonic acid. A dyestuff is thereby evenly formed throughout the emulsion.
- the film is then treated in a conventional azo dye bleach bath to effect destruction of the dye at the silver image, whereupon the film is worked up according to the usual practice. A positive dyestufi image is thereby obtained in the film.
- R is selected from the class consisting of hydrogen and o -a'-on' B. being alkyl
- M is a member selected from the class consisting of hydrogen and a salt forming radical and the brominated derivatives of the aforestated urethanes.
- a photographic silver halide emulsion containlng a color former fast to diffusion comprising a urethane of 2,-naphthyl J-acid of the following formula:
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE488697D BE488697A (en)) | 1948-05-06 | ||
| US25534A US2480815A (en) | 1948-05-06 | 1948-05-06 | 2-naphthyl j-acid and the urethanes thereof as color formers |
| GB9889/49A GB659128A (en) | 1948-05-06 | 1949-04-12 | Improvements in the production of photographic dye images |
| FR985640D FR985640A (fr) | 1948-05-06 | 1949-05-03 | Perfectionnements aux chromogènes utilisés dans la photographie en couleurs |
| CH286148D CH286148A (fr) | 1948-05-06 | 1949-05-06 | Procédé de production d'images colorées dans une émulsion photographique exposée d'halogénure d'argent. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25534A US2480815A (en) | 1948-05-06 | 1948-05-06 | 2-naphthyl j-acid and the urethanes thereof as color formers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2480815A true US2480815A (en) | 1949-08-30 |
Family
ID=21826640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US25534A Expired - Lifetime US2480815A (en) | 1948-05-06 | 1948-05-06 | 2-naphthyl j-acid and the urethanes thereof as color formers |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2480815A (en)) |
| BE (1) | BE488697A (en)) |
| CH (1) | CH286148A (en)) |
| FR (1) | FR985640A (en)) |
| GB (1) | GB659128A (en)) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2591642A (en) * | 1950-01-10 | 1952-04-01 | Gen Aniline & Film Corp | Nondiffusing color formers comprising aryl j-acids in which the aryl radical is provided with a nondiffusing group |
| US4533625A (en) * | 1983-03-25 | 1985-08-06 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive materials |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2367531A (en) * | 1942-06-12 | 1945-01-16 | Eastman Kodak Co | Acylaminophenol photographic couplers |
| US2414491A (en) * | 1945-01-27 | 1947-01-21 | Gen Aniline & Film Corp | Photographic developer |
| US2445252A (en) * | 1947-04-10 | 1948-07-13 | Gen Aniline & Film Corp | Photographic elements containing urethanes of nu-substituted j acids as color formers |
-
0
- BE BE488697D patent/BE488697A/xx unknown
-
1948
- 1948-05-06 US US25534A patent/US2480815A/en not_active Expired - Lifetime
-
1949
- 1949-04-12 GB GB9889/49A patent/GB659128A/en not_active Expired
- 1949-05-03 FR FR985640D patent/FR985640A/fr not_active Expired
- 1949-05-06 CH CH286148D patent/CH286148A/fr unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2367531A (en) * | 1942-06-12 | 1945-01-16 | Eastman Kodak Co | Acylaminophenol photographic couplers |
| US2414491A (en) * | 1945-01-27 | 1947-01-21 | Gen Aniline & Film Corp | Photographic developer |
| US2445252A (en) * | 1947-04-10 | 1948-07-13 | Gen Aniline & Film Corp | Photographic elements containing urethanes of nu-substituted j acids as color formers |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2591642A (en) * | 1950-01-10 | 1952-04-01 | Gen Aniline & Film Corp | Nondiffusing color formers comprising aryl j-acids in which the aryl radical is provided with a nondiffusing group |
| US4533625A (en) * | 1983-03-25 | 1985-08-06 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive materials |
Also Published As
| Publication number | Publication date |
|---|---|
| GB659128A (en) | 1951-10-17 |
| BE488697A (en)) | |
| CH286148A (fr) | 1952-10-15 |
| FR985640A (fr) | 1951-07-20 |
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