US3285747A - Color formers containing a m-alkyl-phenoxyacyl group - Google Patents
Color formers containing a m-alkyl-phenoxyacyl group Download PDFInfo
- Publication number
- US3285747A US3285747A US392330A US39233064A US3285747A US 3285747 A US3285747 A US 3285747A US 392330 A US392330 A US 392330A US 39233064 A US39233064 A US 39233064A US 3285747 A US3285747 A US 3285747A
- Authority
- US
- United States
- Prior art keywords
- group
- alkyl
- color
- coupler
- solution
- 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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- 239000000839 emulsion Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 14
- -1 SILVER HALIDE Chemical class 0.000 claims description 9
- 229910052709 silver Inorganic materials 0.000 claims description 6
- 239000004332 silver Substances 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 238000009792 diffusion process Methods 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- FOGGKKWSFIESMZ-UHFFFAOYSA-N 5-amino-2-(2,4,6-trichlorophenyl)-4h-pyrazol-3-one Chemical compound O=C1CC(N)=NN1C1=C(Cl)C=C(Cl)C=C1Cl FOGGKKWSFIESMZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- WASQBNCGNUTVNI-UHFFFAOYSA-N 2-amino-4,6-dichlorophenol Chemical compound NC1=CC(Cl)=CC(Cl)=C1O WASQBNCGNUTVNI-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- YNAKESQZGPZDDZ-UHFFFAOYSA-N 2-n,2-n-diethylbenzene-1,2-diamine Chemical compound CCN(CC)C1=CC=CC=C1N YNAKESQZGPZDDZ-UHFFFAOYSA-N 0.000 description 1
- PTFIPECGHSYQNR-UHFFFAOYSA-N 3-Pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-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
- AKCDODMHSIQHEF-UHFFFAOYSA-N 5-amino-2-(2-chlorophenyl)-4h-pyrazol-3-one Chemical compound O=C1CC(N)=NN1C1=CC=CC=C1Cl AKCDODMHSIQHEF-UHFFFAOYSA-N 0.000 description 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006185 dispersion 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
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- NGRXSVFCLHVGKU-UHFFFAOYSA-N ethyl 3-(4-nitrophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C([N+]([O-])=O)C=C1 NGRXSVFCLHVGKU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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
- 239000000543 intermediate Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 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
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 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
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 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
- G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
Definitions
- This invention relates to color photography and particularly to color-forming coupler compounds containing a m-alkylphenoxyacylgroup.
- a colored image may beproduced by adding to certain developer solutions or by incorporating in the gelatino silver-halide emulsion, a compound which couples during development with the oxidation products of the developing agent to form a colored substance which is deposited close to the silver grains of the silver image during development.
- a compound which is employed in conjunction with a developing agent for the exposed silver-halide and which couples with the oxidation product of said developing agent during development, is referred to herein .as a coupling component or coupler.
- a coupler In order to be of use in color photography, a coupler must produce. a dye image of suitable stability and spectral' characteristics. In addition to the above properties, a coupler must be capable of being incorporated in a photographic emulsion. and be fast to diffusion. Thus, couplers may be incorporated. in a photographic emulsion by dispersing therein a solution of said coupler in an oily water-immiscible solvent such as tricresyl phosphate, dibutyl phthalate, and. the like. Alternately, couplers may be employed that are alkali soluble and, therefore, can be dissolved directly in the photographic emulsion. In order to render the couplers fast to.
- an oily water-immiscible solvent such as tricresyl phosphate, dibutyl phthalate, and. the like.
- couplers may be employed that are alkali soluble and, therefore, can be dissolved directly in the photographic emulsion. In order
- Another object is to provide a coupler having extremely high solubility in water-immiscible organic solvents.
- a still further object of this invention is to provide color-forming components possessing relatively low meltingrpoints.
- a still further object is to provide photographic emulsions containing color formers, characterized by extremely high solubility in water-immiscible organic solvents and low melting points.
- the above objects are realized by incorporating into one of the usual color coupler molecules, i.e., a ketomethylene compound, a pyrazolone or a. phenol, am-alkylphenoxyacyl residue in which the alkyl radical contains at least carbon atoms.
- Thisgroup maybe readily introduced by conventional methods into color-forming moieties that contain a primary or secondary amino group, a reactive hydroxyl group or other suitable linkages.
- the coupling components thus obtained. are extremely soluble in water-immiscible organic solvents such as tricresyl phosphate, dibutyl phthalate, and the like and possess low melting points, generally 100 C. or lower.
- color couplers contemplated herein can be represented by the following general formulae :1
- R is hydrogen, an alkyl group, i.e., methyl, ethyl, n-propyl, n-butyl, sec.-butyl, amyl", iso-amyl', hexyl, heptyl, etc.;
- R is a long chain alkyl group containing from 10 to 20 carbon: atoms, i.e., capryl, undecylyl, lauryl, myristyl, pentadecyl, palmityl, stearyl, etc;
- R 1 is a methyl group;
- R is hydrogen or an alkyl group as given above for R;
- A represents that part of the molecule that contains the coupling function such as. a reactive methylene or phenolic hydroxyl group capable of coupling with the oxidation products. of a primary aromatic amino color developing agent, and Y is Specific compounds which maybe used according to. this invention are the following:
- the acid chloride of the above compound was prepared by allowing a mixture of carboxylic acid (200 g.) and thionyl chloride (300 ml.) to stand for 24 hours. The resulting solution was degassed and most of the excess thionyl chloride was removed on an aspirator. Finally, the remaining thionyl chloride was removed at below 40 C. under vacuum pump pressure. The residual oil was used without purification.
- the benzene was removed on a steam bath at reduced pressure and the residue was treated with ice and water. The resulting solid was stirred with dilute sodium bicarbonate solution in a Waring Blendor, filtered and dried.
- the product may be used in this form or further purified by crystallization from low boiling petroleum ether (M.P. 57-59.5 C.)
- Example III (1 -hydr0xy-2-naphthoyl -N [a- (3- pentadecylphenoxy -n-batyryl] -1,6-hexanediamine
- Example IV N-(4-chloro-1 -hydroxy-2-naphthoyl)-N (oz (3-pentadecylphen0xy) n batyryl]-1,6-hexanediamine
- This product was prepared in a manner similar to Example III; 78-79 C. from ethanol.
- a suspension of S-amino-1-(2,4',6-trichlorophenyl)- 5-pyrazolone (8.3 g., 0.03 mole) in 100 ml. of N-methyl- 2-pyrrolidone was treated dropwise while stirring at C. with the acid chloride of Example I (12.2 g., 0.03
- Example VI 3- [a- 3 '-pentadecylphen0xy) butyramido] -1-phenyl-5-pyrazol0ne
- the product was prepared in a manner similar to Example V except that 3-amino-l-phenyl-S-pyrazolone was substituted for 3 amino-l-(2',4',6'-trichlorophenyl)-5- pyrazolone; M.P. 63-64 C.
- Example VII.1 (2'-chl0r0phenyl -3- [a- (3 '-pentadecylphenoxy -n-butyramid0] -5-pyraz0l0ne
- This product was prepared in the same manner as Example V except that 3amino-1-(2'-chlorophenyl)-5- pyrazolone was substituted for the 3-amino-l-(2',4',6- trichlorophenyl)-5-pyrazolone.
- the product was crystallized from aceonitrile and melted at 84-85 C.
- Example VIIl.a-benz0yl-3-[a-(3'-pentadecylphenoxyl)- n-butyramia'o]-acetanilide The amine of the following constitution:
- Example X A solution of 1.5 g. of coupler was dissolved in 6.0 g. of a mixture consisting of 50 parts of phenethyl alcohol, 40 parts of tricresyl phosphate and 10 parts of nbutyl phthalate and the resulting solution dispersed in 20 ml. of a 6% gelatin solution containing .05 ml. of lauryl sulfate. Emulsification was effected by high-speed agitation in a small Waring Blendor. The above dispersion of coupler was mixed with 50 g. of a melted silver-halide gelatin emulsion and then coated on a suitable support, set and dried in the usual manner. On exposure and development of this emulsion with a developing solution employing Z-amino-S-diethylaminotoluene as the developing agent and subsequent removal of silver, a colored image was obtained.
- the primary aromatic amino developing agents are generally suitable including the phenylenediamines and aminophenols.
- the alkyl phenylenediamines may be substituted in the amino group as well as in the ring.
- Suitable compounds are 4-aminoaniline, 4-ethylaminoaniline, 2-diethylaminoaniline, 4-dialkylaminoaniline, e.g., 4-dimethylamin0aniline, 4 diethylaminoaniline, 4-[N-(fl-hydroxyethyD-N- ethyl]aminoaniline, 4 amino-N-ethyl-N-(fi-methanesulfonamidoethyl)-2-methylaniline sulfate, and the like.
- the above developing agents are preferably used in the form of their salts such as the hydrochloride or hydrosulfate as they are more soluble and stable than the free bases.
- All of these compounds have a primary amino group which enables the oxidation product of the developer to couple with the color compounds to form dye images. After removal of the silver image by bleaching and fixing in a manner well-known to the art, the color image remains in the emulsion.
- a suitable developing solution can be prepared as follows:
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Description
United States Patent 3,285,747- COLOR FORMERS CONTAINING A m-ALKYL- PHENOXYACYL GROUP Robert F. Coles, North St. Paul, Minn., assignor to General Analiue & Film Corporation, New York, N.Y., a corporation of Delaware No Drawing. Filed Aug. 26, 1964, Ser. No. 392,330 3 Claims. (Cl. 96100) This application is a continuation-impart of application Serial No. 681,884,- filed September 4, 1957, now abandoned.
This invention relates to color photography and particularly to color-forming coupler compounds containing a m-alkylphenoxyacylgroup.
' It is known that a colored image may beproduced by adding to certain developer solutions or by incorporating in the gelatino silver-halide emulsion, a compound which couples during development with the oxidation products of the developing agent to form a colored substance which is deposited close to the silver grains of the silver image during development. Such a compound, which is employed in conjunction with a developing agent for the exposed silver-halide and which couples with the oxidation product of said developing agent during development, is referred to herein .as a coupling component or coupler.
In order to be of use in color photography, a coupler must produce. a dye image of suitable stability and spectral' characteristics. In addition to the above properties, a coupler must be capable of being incorporated in a photographic emulsion. and be fast to diffusion. Thus, couplers may be incorporated. in a photographic emulsion by dispersing therein a solution of said coupler in an oily water-immiscible solvent such as tricresyl phosphate, dibutyl phthalate, and. the like. Alternately, couplers may be employed that are alkali soluble and, therefore, can be dissolved directly in the photographic emulsion. In order to render the couplers fast to. diffusion in the gelatino silver-halide emulsion, it is usual to introduce into the coupler molecule a. molecule enlarging group such as a long alkyl chain. Although the prior art contains numerous patents on color formers, very few of them possess the aforementioned properties which render them suitable for use in color photography.
It is, therefore, an object of this invention to provide a coupler characterized by improved fastness to diffusion in a photographic emulsion.
Another object is to provide a coupler having extremely high solubility in water-immiscible organic solvents.
A still further object of this invention is to provide color-forming components possessing relatively low meltingrpoints.
A still further object is to provide photographic emulsions containing color formers, characterized by extremely high solubility in water-immiscible organic solvents and low melting points.
Other objects and advantages of this invention will be apparent as the description proceeds.
The above objects are realized by incorporating into one of the usual color coupler molecules, i.e., a ketomethylene compound, a pyrazolone or a. phenol, am-alkylphenoxyacyl residue in which the alkyl radical contains at least carbon atoms. Thisgroup maybe readily introduced by conventional methods into color-forming moieties that contain a primary or secondary amino group, a reactive hydroxyl group or other suitable linkages. The coupling components thus obtained. are extremely soluble in water-immiscible organic solvents such as tricresyl phosphate, dibutyl phthalate, and the like and possess low melting points, generally 100 C. or lower. This property is highly desirable in a dispersed droplet type of color former and dye system, since it produces a system which hasonly a slight tendency toward crystallization. In fact, the aforesaid properties of highsolubility in organic solvents and low melting point make these couplers particularly suitable in mixed-grain type emulsions.
The color couplers contemplated herein can be represented by the following general formulae :1
wherein R is hydrogen, an alkyl group, i.e., methyl, ethyl, n-propyl, n-butyl, sec.-butyl, amyl", iso-amyl', hexyl, heptyl, etc.; R is a long chain alkyl group containing from 10 to 20 carbon: atoms, i.e., capryl, undecylyl, lauryl, myristyl, pentadecyl, palmityl, stearyl, etc; R 1 is a methyl group; R is hydrogen or an alkyl group as given above for R; A represents that part of the molecule that contains the coupling function such as. a reactive methylene or phenolic hydroxyl group capable of coupling with the oxidation products. of a primary aromatic amino color developing agent, and Y is Specific compounds which maybe used according to. this invention are the following:
N-(1hydroxy-2-n aph'thoy1)-N.'-[or(3-pentadecylphenoxy)- n=butyryl1 -'1,6 hexanediamine N (4-chloro-1-hydr0xy-2-naphthoyl N'- ['a- 3-pentadecy1- phenoxy) -n.-butry1]-1,6-hexanedia1nine This invention is further illustrated by the following examples but it is to be understood that the invention is not to be restrictedthereto.
PREPARATION OF INTERMEDIATES Example IL-a-( m-pentadecylphenoxy.)-nrbutyric acid In a 3-liter triple-necked flask, equippedawith a reflux condenser, stirrer and dropping funnel was placed a solution of m-pentadecylphenol (608 g., 2.0 moles) in 1300 ml; of ethanol containing 16.0 g. (4.0.moles) ofso dium hydroxide. The solution was cooled slightly in water and a-bromobutyric acid (334 g., 2.0 moles) was added at a rate sufiicient to cause a gentle reflux. The mixture was heated at reflux for 3 hours and then an additional 20 g. of sodium hydroxide and 42 g. of a-bromobutyric acid were added and heating continued for 3 hours. A second and third addition was made in the same manner. The solution was then poured into 4- liters of ice Water and acidified strongly with hydrochloric acid. After collecting the precipitated product and washing with water, the material was Washed with cold methanol and then recrystallized from 2-liters of methanol. Yield 600 g., M.P. 81-84 C.
The acid chloride of the above compound was prepared by allowing a mixture of carboxylic acid (200 g.) and thionyl chloride (300 ml.) to stand for 24 hours. The resulting solution was degassed and most of the excess thionyl chloride was removed on an aspirator. Finally, the remaining thionyl chloride was removed at below 40 C. under vacuum pump pressure. The residual oil was used without purification.
PREPARATION OF COLOR FORMERS Example II.4,6-dichlr0-2-[a-(3'-pentadecylphenoxy)- n-butyramido] -phen0l To a solution of 2-amino-4,6-dichlorophenol (26.7 g., 0.15 mole) in dry benzene (350 ml.) was added potassium acetate (15 g., 0.15 mole). After cooling to 10 C., the acid chloride prepared in Example I (61.5 g., 0.15 mole) was added dropwise with stirring. The reaction mixture was stirred cold for 3 hours and then on a steam bath for 1 hour. Decolorizing carbon was added and the mixture filtered. The benzene was removed on a steam bath at reduced pressure and the residue was treated with ice and water. The resulting solid was stirred with dilute sodium bicarbonate solution in a Waring Blendor, filtered and dried. The product may be used in this form or further purified by crystallization from low boiling petroleum ether (M.P. 57-59.5 C.)
Example III .-N (1 -hydr0xy-2-naphthoyl -N [a- (3- pentadecylphenoxy -n-batyryl] -1,6-hexanediamine The amine of the following constitution:
was prepared by reacting phenyl l-hydroxy-Z-naphthoate and a 4 mole excess of examethylenediamine in cold benzene.
A solution of the resulting amine (14.3 g., 0.05 mole) in dry benzene (100 ml.) was cooled in ice and the acid chloride of Example I (20.5 g., 0.05 mole) was added dropwise with stirring. Triethylarnine (29 ml., 0.25 mole) was added dropwise. The reaction mixture was stirred cold for 2 hours and then heated for 2 hours. After filtering, the solvents were removed at reduced pressure and the residue diluted with 100 ml. of petroleum ether; B.P. 30-60 C. The solution was cooled in ice, and the solid collected and crystallized from ethanol. Yield 22 g., M.P. 9294 C.
Example IV. N-(4-chloro-1 -hydroxy-2-naphthoyl)-N (oz (3-pentadecylphen0xy) n batyryl]-1,6-hexanediamine This product was prepared in a manner similar to Example III; 78-79 C. from ethanol. Example V.1-(2,4,6'-trichl0rophenyl)-3-[a-(3'-pentadecylphenoxy)-n-butyramid0]-5-pyraz0l0ne A suspension of S-amino-1-(2,4',6-trichlorophenyl)- 5-pyrazolone (8.3 g., 0.03 mole) in 100 ml. of N-methyl- 2-pyrrolidone was treated dropwise while stirring at C. with the acid chloride of Example I (12.2 g., 0.03
Example VI .3- [a- 3 '-pentadecylphen0xy) butyramido] -1-phenyl-5-pyrazol0ne The product was prepared in a manner similar to Example V except that 3-amino-l-phenyl-S-pyrazolone was substituted for 3 amino-l-(2',4',6'-trichlorophenyl)-5- pyrazolone; M.P. 63-64 C.
Example VII.1 (2'-chl0r0phenyl -3- [a- (3 '-pentadecylphenoxy -n-butyramid0] -5-pyraz0l0ne This product was prepared in the same manner as Example V except that 3amino-1-(2'-chlorophenyl)-5- pyrazolone was substituted for the 3-amino-l-(2',4',6- trichlorophenyl)-5-pyrazolone. The product was crystallized from aceonitrile and melted at 84-85 C.
Example VIIl.a-benz0yl-3-[a-(3'-pentadecylphenoxyl)- n-butyramia'o]-acetanilide The amine of the following constitution:
NHQ
was prepared by the reaction of ethyl benzoylacetate and m-nitroaniline in boiling xylene followed by catalytic reduction of the nitro compound with platinum oxide.
A solution of the above amine hydrochloride (4.4 g., 0.015 mole) in dry pyridine (25 ml.) was chilled in ice and treated dropwise with 6.1 g. (0.015 mole) of the acid chloride from Example I. The reaction mixture was allowed to stand several hours at room temperature and then poured into ice and water containing excess hydrochloric acid. The solid was collected and washed with water and cold methanol. The product was crystallized from about 300 ml. of methanol to yield 5.2 g. of a colorless product; M.P. 55-56 C.
Example IX. N-{p-[N'-benzyl-N'-(p-tolyl)sulfamyl] phenyl} a-{p-[a-(3-pentadecylphenoxy)butyramido] benz0yl}acetamide The amine of the following structure:
was prepared by the reaction of ethyl p-nitrobenzoyl acetate and N-benzyl-N'-(p-tolyl)sulfanilamide followed by the catalytic reduction of the nitro group.
The product was prepared as in Example VIII.
The following example illustrates the manner whereby the couplers herein described are incorporated in a gelatin emulsion.
Example X A solution of 1.5 g. of coupler was dissolved in 6.0 g. of a mixture consisting of 50 parts of phenethyl alcohol, 40 parts of tricresyl phosphate and 10 parts of nbutyl phthalate and the resulting solution dispersed in 20 ml. of a 6% gelatin solution containing .05 ml. of lauryl sulfate. Emulsification was effected by high-speed agitation in a small Waring Blendor. The above dispersion of coupler was mixed with 50 g. of a melted silver-halide gelatin emulsion and then coated on a suitable support, set and dried in the usual manner. On exposure and development of this emulsion with a developing solution employing Z-amino-S-diethylaminotoluene as the developing agent and subsequent removal of silver, a colored image was obtained.
Various photographic developing agents can be employed with the couplers of my invention. The primary aromatic amino developing agents are generally suitable including the phenylenediamines and aminophenols. The alkyl phenylenediamines may be substituted in the amino group as well as in the ring. Suitable compounds are 4-aminoaniline, 4-ethylaminoaniline, 2-diethylaminoaniline, 4-dialkylaminoaniline, e.g., 4-dimethylamin0aniline, 4 diethylaminoaniline, 4-[N-(fl-hydroxyethyD-N- ethyl]aminoaniline, 4 amino-N-ethyl-N-(fi-methanesulfonamidoethyl)-2-methylaniline sulfate, and the like. The above developing agents are preferably used in the form of their salts such as the hydrochloride or hydrosulfate as they are more soluble and stable than the free bases. All of these compounds have a primary amino group which enables the oxidation product of the developer to couple with the color compounds to form dye images. After removal of the silver image by bleaching and fixing in a manner well-known to the art, the color image remains in the emulsion.
A suitable developing solution can be prepared as follows:
G. 2-amino-5-diethylaminotoluene 2 Sodium carbonate (anhydrous) 20 Sodium sulfite (anhydrous) 2 Potassium bromide 0.2
Water to make 1 liter.
The exposed silver-halide emulsions containing the color formers are developed in the above solution in the usual manner. 1
It will be understood that the examples and modifications set forth herein are illustrative only and my invention is to be taken as limited only by the scope of the appended claims.
I claim:
1. A silver halide emulsion containing a coupler compound selected from the class consisting of compounds having one of the following general formula:
2. A silver-halide emulsion containing a coupler compound of the following formula:
' ii t C-N(OH2)aNlCO 3. A silver-halide emulsion containing a coupler compound of the following formula:
OH u i i I i -o-N-(oH,)-No-( Jo- References Cited by the Examiner UNITED STATES PATENTS 2,330,291 9/1943 Kirby 96-100 2,367,531 1/1945 Salminen et al. 96-100 2,423,730 7/1947 Salminen et al. 96-100 40 2,772,161 11/1956 Loria et al. 96-100 X 2,808,329 10/1957 Whitmore 96-100 2,829,975 4/1958 Popeck et al. 96-100 X 2,860,974 11/ 1958 Williams 96-100 2,908,573 10/ 1959 Bush et al. 96-100 5 2,920,961 1/ 1960 Bush et al. 96-100 NORMAN G. TORCHIN, Primary Examiner. J. T. BROWN, D. D. PRICE, Assistant Examiners.
Claims (1)
1. A SILVER HALIDE EMULSION CONTAINING A COUPLER COMPOUND SELECTED FROM THE CLASS CONSISTING OF COMPOUNDS HAVING ONE OF THE FOLLOWING GENERAL FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US392330A US3285747A (en) | 1964-08-26 | 1964-08-26 | Color formers containing a m-alkyl-phenoxyacyl group |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US392330A US3285747A (en) | 1964-08-26 | 1964-08-26 | Color formers containing a m-alkyl-phenoxyacyl group |
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| Publication Number | Publication Date |
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| US3285747A true US3285747A (en) | 1966-11-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US392330A Expired - Lifetime US3285747A (en) | 1964-08-26 | 1964-08-26 | Color formers containing a m-alkyl-phenoxyacyl group |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3658537A (en) * | 1967-11-18 | 1972-04-25 | Agfa Gevaert Ag | Color photographic material comprising a blue-green color coupler |
| US3891445A (en) * | 1973-06-20 | 1975-06-24 | Fuji Photo Film Co Ltd | Color photographic light-sensitive materials |
| US11809912B2 (en) | 2020-12-09 | 2023-11-07 | Dell Products L.P. | System and method for allocating resources to perform workloads |
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| US2367531A (en) * | 1942-06-12 | 1945-01-16 | Eastman Kodak Co | Acylaminophenol photographic couplers |
| US2772161A (en) * | 1954-10-14 | 1956-11-27 | Eastman Kodak Co | Photographic emulsions and new coupling compounds |
| US2808329A (en) * | 1954-11-22 | 1957-10-01 | Eastman Kodak Co | Photographic color correction using colored and uncolored couplers |
| US2829975A (en) * | 1956-04-26 | 1958-04-08 | Gen Aniline & Film Corp | 3-alpha-sulfo acylamino pyrazolone color formers in which the acyl group contains a long aliphatic chain |
| US2908573A (en) * | 1956-07-25 | 1959-10-13 | Eastman Kodak Co | Photographic color couplers containing mono-n-alkyl groups |
| US2920961A (en) * | 1957-07-29 | 1960-01-12 | Eastman Kodak Co | Couplers for color photography |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2330291A (en) * | 1939-10-24 | 1943-09-28 | Du Pont | Dye intermediate |
| US2367531A (en) * | 1942-06-12 | 1945-01-16 | Eastman Kodak Co | Acylaminophenol photographic couplers |
| US2423730A (en) * | 1942-06-12 | 1947-07-08 | Eastman Kodak Co | Acylamino phenols |
| US2772161A (en) * | 1954-10-14 | 1956-11-27 | Eastman Kodak Co | Photographic emulsions and new coupling compounds |
| US2808329A (en) * | 1954-11-22 | 1957-10-01 | Eastman Kodak Co | Photographic color correction using colored and uncolored couplers |
| US2860974A (en) * | 1954-11-22 | 1958-11-18 | Eastman Kodak Co | Photographic color correction process |
| US2829975A (en) * | 1956-04-26 | 1958-04-08 | Gen Aniline & Film Corp | 3-alpha-sulfo acylamino pyrazolone color formers in which the acyl group contains a long aliphatic chain |
| US2908573A (en) * | 1956-07-25 | 1959-10-13 | Eastman Kodak Co | Photographic color couplers containing mono-n-alkyl groups |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3658537A (en) * | 1967-11-18 | 1972-04-25 | Agfa Gevaert Ag | Color photographic material comprising a blue-green color coupler |
| US3891445A (en) * | 1973-06-20 | 1975-06-24 | Fuji Photo Film Co Ltd | Color photographic light-sensitive materials |
| US11809912B2 (en) | 2020-12-09 | 2023-11-07 | Dell Products L.P. | System and method for allocating resources to perform workloads |
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