US2728660A - Salicylic acid ester and amide photographic coupler compounds - Google Patents
Salicylic acid ester and amide photographic coupler compounds Download PDFInfo
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- US2728660A US2728660A US385704A US38570453A US2728660A US 2728660 A US2728660 A US 2728660A US 385704 A US385704 A US 385704A US 38570453 A US38570453 A US 38570453A US 2728660 A US2728660 A US 2728660A
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- US
- United States
- Prior art keywords
- coupler
- salicylic acid
- compounds
- amide
- color
- 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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- 150000001875 compounds Chemical class 0.000 title claims description 24
- 150000001408 amides Chemical class 0.000 title description 4
- 150000003902 salicylic acid esters Chemical class 0.000 title description 4
- 239000000839 emulsion Substances 0.000 claims description 21
- -1 SILVER HALIDE Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 13
- 229910052709 silver Inorganic materials 0.000 claims description 8
- 239000004332 silver Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000010410 layer Substances 0.000 description 19
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000000975 dye Substances 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 239000000463 material Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229960004889 salicylic acid Drugs 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- DVZPQHRWOUXUPU-UHFFFAOYSA-N 4-ethoxy-2-hydroxybenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C(O)=C1 DVZPQHRWOUXUPU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UUGLJVMIFJNVFH-UHFFFAOYSA-N Hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000010452 phosphate Substances 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
- 238000006467 substitution reaction Methods 0.000 description 2
- TWRIKPDUZDNYAM-UHFFFAOYSA-N (4-pentan-2-ylphenyl)-phenylmethanone Chemical compound C1=CC(C(C)CCC)=CC=C1C(=O)C1=CC=CC=C1 TWRIKPDUZDNYAM-UHFFFAOYSA-N 0.000 description 1
- PCKKNFLLFBDNPA-UHFFFAOYSA-N 1,1-dibutylurea Chemical compound CCCCN(C(N)=O)CCCC PCKKNFLLFBDNPA-UHFFFAOYSA-N 0.000 description 1
- XMTQHQNLBMWCCB-UHFFFAOYSA-N 1-N,4-N-dimethylbenzene-1,4-diamine sulfuric acid Chemical compound S(=O)(=O)(O)O.CNC1=CC=C(C=C1)NC XMTQHQNLBMWCCB-UHFFFAOYSA-N 0.000 description 1
- AIDFJGKWTOULTC-UHFFFAOYSA-N 1-butylsulfonylbutane Chemical compound CCCCS(=O)(=O)CCCC AIDFJGKWTOULTC-UHFFFAOYSA-N 0.000 description 1
- HRBLHUVHOWWBEN-UHFFFAOYSA-N 1-n,4-n-diethylbenzene-1,4-diamine;hydrochloride Chemical compound Cl.CCNC1=CC=C(NCC)C=C1 HRBLHUVHOWWBEN-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical class COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- YSOKMOXAGMIZFZ-UHFFFAOYSA-N 2,4-dinitrophenetole Chemical compound CCOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YSOKMOXAGMIZFZ-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- CGNOCUSLPSCMLL-UHFFFAOYSA-N 3-o-benzyl 1-o-ethyl propanedioate Chemical compound CCOC(=O)CC(=O)OCC1=CC=CC=C1 CGNOCUSLPSCMLL-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- WBRKGYSFSCHLKM-UHFFFAOYSA-N 4-n-ethylbenzene-1,4-diamine;hydrochloride Chemical compound Cl.CCNC1=CC=C(N)C=C1 WBRKGYSFSCHLKM-UHFFFAOYSA-N 0.000 description 1
- CCUXJJLBGWMSRP-UHFFFAOYSA-N 4-oxo-4-(oxolan-2-ylmethoxy)butanoic acid Chemical compound OC(=O)CCC(=O)OCC1CCCO1 CCUXJJLBGWMSRP-UHFFFAOYSA-N 0.000 description 1
- CQTNADUPUYDXPK-UHFFFAOYSA-N C(C=1C(C(=O)O)=CC=CC1)(=O)OCCCC.C(C=1C(C(=O)O)=CC=CC1)(=O)OC Chemical compound C(C=1C(C(=O)O)=CC=CC1)(=O)OCCCC.C(C=1C(C(=O)O)=CC=CC1)(=O)OC CQTNADUPUYDXPK-UHFFFAOYSA-N 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- BEZQTEBPMMEPNB-UHFFFAOYSA-N ethyl 4-amino-2-hydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(N)C=C1O BEZQTEBPMMEPNB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DSICTTBMRSZYJL-UHFFFAOYSA-N ethyl n,n-dibutylcarbamate Chemical compound CCCCN(CCCC)C(=O)OCC DSICTTBMRSZYJL-UHFFFAOYSA-N 0.000 description 1
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 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
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- WZKOKGOAHBIPCI-UHFFFAOYSA-N n,n,4-trimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(C)C=C1 WZKOKGOAHBIPCI-UHFFFAOYSA-N 0.000 description 1
- OOYRLFIIUVBZSY-UHFFFAOYSA-N n,n-diethyldecanamide Chemical compound CCCCCCCCCC(=O)N(CC)CC OOYRLFIIUVBZSY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YXVQQPCWKVLQER-UHFFFAOYSA-N n-butyl-4-(4-methylphenyl)sulfonylbutan-1-amine Chemical compound CCCCNCCCCS(=O)(=O)C1=CC=C(C)C=C1 YXVQQPCWKVLQER-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- 229960000581 salicylamide Drugs 0.000 description 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical class OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- JQMQIRDMGUZAOM-UHFFFAOYSA-N tris(4-butylphenyl) phosphate Chemical compound C1=CC(CCCC)=CC=C1OP(=O)(OC=1C=CC(CCCC)=CC=1)OC1=CC=C(CCCC)C=C1 JQMQIRDMGUZAOM-UHFFFAOYSA-N 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
- G03C7/346—Phenolic couplers
Definitions
- Salicylic acid and certain substituted salicylic acids such as p-amino salicylic acid have been mentioned as useful as coupler compounds in the color development process of color photography.
- salicylic acid there is little use for salicylic acid in color development processes where it is desired to obtain non-dilfusing dye images and dye images having good stability inasmuch as salicylic acid couples very poorly with the oxidation products of color developing agents, it produces very unstable dyes and indeed the dye images therefrom readily diffuse from the hydrophilic organic colloid emulsion layers.
- dye images obtained from salicylic acid in the, color development process are so soluble that they may be readily washed from an emulsion layer during the processing steps customarily following the color development step. 1
- salicylic acid amides including the salicylic acid anilides
- salicylic acid esters having an electron-donating substituent in the nuclear position para to the amide or ester group, have greatly improved coupling rates in color development processes and yield much more stable dye images compared to either salicylic acid or unsubstituted salicylic acid amides.
- salicylic acid derivatives having the indicated electron-donating group, with which our invention is concerned and which can be used in the color development of exposed silver halide emulsion layers therefore have the following general formulas:
- R represents an alkoxyl group e. g. methoxyl or an electron-donating substitutent such as an amino group, an acylamido group, e. g. acetamido, benzamido, stearamido, etc.
- R1 represents an alkyl group of the order of l-20 or more carbon atoms, or a monocyclic aryl group, e. g., methyl, ethyl, n-propyl, n-butyl, stearyl, phenyl, o-tolyl, m-chlorophenyl, etc.
- R2 represents a hydrogen atom, alkyl or aryl groups as indicated above.
- the salicyl nuclei of the couplers may be further substituted with, for example, alkyl groups such as methyl to change the color of the dye obtained from the couplers or other groups such as solubilizing groups which do not impair the electron-donating function of the substitutent in the para position.
- the following compounds have one of the above general formulas and are representative of the coupling compounds contemplated by our invention.
- the compounds all produce cyan dye images when used in color development processes.
- Coupler No. 1 was prepared according to Drain et al. (J. C. S. 1949, 1498-1503).
- Coupler No. 2 was prepared from 2.59 parts of 2-carbophenoxy-S-nitrophenol (BeiL, 10, 118) heated with 1.12 parts of aniline at 180-200 C. for 1 hour and the phenol formed was distilled out.
- the product, 2-phenylcarbamyl-S-nitrophe'nol II was recrystallized from volumes of alcohol. Two parts of II in 50 volumes of alcohol were catalytically reduced, the solution filtered, evaporated to a syrup and allowed to crystallize to yield the product, coupler No. 2.
- the simple amide and lower alkyl amides corresponding to coupler No. 2 are prepared similarly using ammonia or the required alkyl amine in place of aniline.
- Coupler No. 3 was prepared by the same method as that used for preparing coupler No. 2 except substituting an equivalent amount of octadecyl amine for aniline.
- Coupler No. 4 was prepared as follows:
- Coupler No. 5 was prepared as was coupler No. 4, benzoyl chloride being used in place of acetyl chloride.
- Coupler No. 6 was prepared as follows:
- Coupler No. 8 was prepared as follows:
- 4-ethoxysalicylic acid was prepared according to Perkin (J. C. S. 67, 995) or Gregor (Monatsh. 16, 891).
- Coupler No. 9 was prepared according to Perkin (J. C. S. 67, 995).
- Coupler No. 10 was prepared as follows:
- Coupler No. 11 was prepared as follows:
- Coupler No. 12 was prepared inthe manner of coupler No. 11, octadecylamine being used'in place of aniline.
- couplers such as couplers No. 3, 7, 8 and 12 containing the stearamido group, octadecyl group, or other high molecular weight groups are particularly non diffusing in 'hydrophilic colloid silver halide emulsion layers and are therefore particularly adapted to dispersion in emulsion layers by means of crystalloidal materials alone or together with other coupler compounds such as known colored couplers used for color correction purposes,
- the crystalloidal materials which are used for dispersing the above coupler compounds in hydrophilic photographic emulsion layers are water-insoluble, organic, crystalloidal materials having boiling points above about 175 C.
- the crystalloidal materials have a high solvent action for the color formers as well as for the dye images formed therefrom.
- crystalloidal materials useful in our invention are N,N-diethylcapramide, di-n-butylphthalate, N-n-amylphthalimide, tetrahydrofurfuryl benzoate, triphenyl phosphate, n-butyl sulfone, ethyl-N,N-di-n-butylcarbamate, ethyl-N-phenylcarbamate, tetrahydrofurfuryl succinate, ethyl benzyl malonate, methyl phthalate n-butyl phthalate, n-amyl phthalate, 8- methoxyethyl phthalate, .B-ethoxyethyl phthalate, p-butoxyethyl phthalate, butyl o-methoxy benzoate, n-hexyl benzoate, benzophenone, p-sec-amylbenzophenone, tricresyl
- Emulsion layers containing such dispersions of the couplers are useful in both reversal and negative-positive color development processes of the well known types.
- couplers Nos. 1, 2, 4, 5, 6, 9, l0 and 11 which are somewhat more difiusible in emulsion layers in the presence of aqueous processing solutions can, however, be used alone or together with other couplers in emulsion layers for various purposes.
- couplers which are more soluble in aqueous alkaline color developing solutions are representative of couplers of the invention which are particularly adapted to use in color developing solutions used for the development of exposed silver halide emulsion layers devoid of coupler compounds such as those employed in well known reversal color development processes.
- the couplers of the invention When the coupler compounds of the invention are employed in emulsion layers of multilayer color films, the couplers can be employed in the red-sensitive cyan image-forming emulsion in the required amount. Accordingly, when the more soluble coupler compounds indicated are employed in the color developing solution, the developing solution can be used for the development of the red-sensitive cyan emulsion layer in the case of a multi-layer color film sensitized in the natural order.
- a developer composition suitable for use in the development of exposed silver halide emulsion layers in either reversal or negative-positve color processes is provided as follows:
- the aromatic amino developing agents used with the coupler compounds of our invention include the mono-, diand triaminoaryl compounds and their derivatives formed by substitution in the amino group as well as in the ring such as alkylphenylenediamines and alkyltoluylenediamines.
- the compounds are usually used in the salt form, such as the hydrochloride or the sulfate, which are more stable than the amines themselves. Suitable compounds are diethyl-p-phenylenediamine hydrochloride, monoethyl-p-phenylenediamine hydrochloride, dimethylp-phenylenediamine sulfate.
- .Patent 2,196,739 are also suitable.
- the p-aminophenols and their substitution products may also be used where the amino group is unsubstituted. All of these compounds have an unsubstituted amino group which enables the oxidation products of the developer to couple with the color-forming compounds to form a dye image.
- the support for the emulsion may be a transparent material such as glass, cellulose ester or a non-transparent reflecting material such as paper or an opaque cellulose ester.
- the emulsion may be coated as a single layer on the support or as a superposed layer on one or both sides of the support. 7
- the method of producing a colored photographic image in an exposed silver halide emulsion layer which comprises developing the exposed emulsion layer with a primary aromatic amino silver halide developing agent in the presence of a coupler compound selected from the class consisting of compounds having the following general formulas:
- R represents a member of the class consisting of amino and acylamido groups
- R1 represents a member of the class consisting of an alkyl group of from 1 to 20 carbon atoms and a monocyclic aryl group of the hen- 2,728,660 5 6 zene series
- R2 represents a member of theclass con- References Cited in the file of this patent sisting of a hydrogen atom, an alkyl group of from 1 UNITED STATES PATENTS to 20 carbon atoms, and a rronocyclic aryl group of the benzene series 2,357,394 Frohlich et a1 Sept. 5, 1944 2.
- a photographic silver halide emulsion layer con- 5 $369,929 vlttufn et 1945 taining a coupler compound designated in claim 1.
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- 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE532448D BE532448A (en)van) | 1953-10-12 | ||
| US385704A US2728660A (en) | 1953-10-12 | 1953-10-12 | Salicylic acid ester and amide photographic coupler compounds |
| GB29175/54A GB754306A (en) | 1953-10-12 | 1954-10-11 | Photographic colour development empolying colour couplers |
| FR1109765D FR1109765A (fr) | 1953-10-12 | 1954-10-12 | Procédé de photographie en couleurs et nouveaux produits pour la mise en oeuvre dece procédé |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US385704A US2728660A (en) | 1953-10-12 | 1953-10-12 | Salicylic acid ester and amide photographic coupler compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2728660A true US2728660A (en) | 1955-12-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US385704A Expired - Lifetime US2728660A (en) | 1953-10-12 | 1953-10-12 | Salicylic acid ester and amide photographic coupler compounds |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2728660A (en)van) |
| BE (1) | BE532448A (en)van) |
| FR (1) | FR1109765A (en)van) |
| GB (1) | GB754306A (en)van) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3520690A (en) * | 1965-06-25 | 1970-07-14 | Fuji Photo Film Co Ltd | Process for controlling dye gradation in color photographic element |
| US4200466A (en) * | 1975-09-30 | 1980-04-29 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide photographic materials |
| US4543322A (en) * | 1983-03-31 | 1985-09-24 | Fuji Photo Film Co., Ltd. | Process for the processing of color photographic silver halide light-sensitive material |
| US4708953A (en) * | 1984-09-13 | 1987-11-24 | Nihon Tokushu Noyaku Seizo K.K. | Salicylamide derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5674666A (en) * | 1996-10-31 | 1997-10-07 | Eastman Kodak Company | Photographic elements containing new cyan dye-forming coupler providing improved color reproduction |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2357394A (en) * | 1940-07-12 | 1944-09-05 | Gen Aniline & Film Corp | Photographic emulsion |
| US2369929A (en) * | 1943-03-18 | 1945-02-20 | Eastman Kodak Co | Acylamino phenol couplers |
| US2423730A (en) * | 1942-06-12 | 1947-07-08 | Eastman Kodak Co | Acylamino phenols |
-
0
- BE BE532448D patent/BE532448A/xx unknown
-
1953
- 1953-10-12 US US385704A patent/US2728660A/en not_active Expired - Lifetime
-
1954
- 1954-10-11 GB GB29175/54A patent/GB754306A/en not_active Expired
- 1954-10-12 FR FR1109765D patent/FR1109765A/fr not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2357394A (en) * | 1940-07-12 | 1944-09-05 | Gen Aniline & Film Corp | Photographic emulsion |
| US2423730A (en) * | 1942-06-12 | 1947-07-08 | Eastman Kodak Co | Acylamino phenols |
| US2369929A (en) * | 1943-03-18 | 1945-02-20 | Eastman Kodak Co | Acylamino phenol couplers |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3520690A (en) * | 1965-06-25 | 1970-07-14 | Fuji Photo Film Co Ltd | Process for controlling dye gradation in color photographic element |
| US4200466A (en) * | 1975-09-30 | 1980-04-29 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide photographic materials |
| US4543322A (en) * | 1983-03-31 | 1985-09-24 | Fuji Photo Film Co., Ltd. | Process for the processing of color photographic silver halide light-sensitive material |
| US4708953A (en) * | 1984-09-13 | 1987-11-24 | Nihon Tokushu Noyaku Seizo K.K. | Salicylamide derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1109765A (fr) | 1956-02-01 |
| GB754306A (en) | 1956-08-08 |
| BE532448A (en)van) |
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