US2338676A - Phenolic coupler compound - Google Patents
Phenolic coupler compound Download PDFInfo
- Publication number
- US2338676A US2338676A US422699A US42269941A US2338676A US 2338676 A US2338676 A US 2338676A US 422699 A US422699 A US 422699A US 42269941 A US42269941 A US 42269941A US 2338676 A US2338676 A US 2338676A
- Authority
- US
- United States
- Prior art keywords
- coupler
- compounds
- positions
- color
- photographic
- 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
Links
- 150000001875 compounds Chemical class 0.000 title description 27
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title description 21
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000000975 dye Substances 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- -1 2,5-disubstituted phenols Chemical class 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 229910052709 silver Inorganic materials 0.000 description 7
- 239000004332 silver Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- RSWJLLSRQRPPPG-UHFFFAOYSA-N 5-methyl-2-prop-2-enylphenol Chemical compound CC1=CC=C(CC=C)C(O)=C1 RSWJLLSRQRPPPG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FXAXRZWXQNNSFY-UHFFFAOYSA-N 3,5-dimethyl-2-prop-1-enylphenol Chemical compound CC=CC1=C(C)C=C(C)C=C1O FXAXRZWXQNNSFY-UHFFFAOYSA-N 0.000 description 1
- VJBNTMUSFMRWSH-UHFFFAOYSA-N 3,5-dimethyl-2-prop-2-enylphenol Chemical compound CC1=CC(C)=C(CC=C)C(O)=C1 VJBNTMUSFMRWSH-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
- 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
- IJJSFSXLZYFTKV-UHFFFAOYSA-N 4-n-methylbenzene-1,4-diamine;hydrochloride Chemical compound Cl.CNC1=CC=C(N)C=C1 IJJSFSXLZYFTKV-UHFFFAOYSA-N 0.000 description 1
- XNDYVSFPOYDCRF-UHFFFAOYSA-N 5-methyl-2-prop-1-enylphenol Chemical compound CC=CC1=CC=C(C)C=C1O XNDYVSFPOYDCRF-UHFFFAOYSA-N 0.000 description 1
- 241000974482 Aricia saepiolus Species 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- This invention relates to photographic color forming or coupling compounds and particularly to substituted phenolic coupler compounds.
- Phenolic coupler compounds have been described in prior patents such as Fischer U. S. Patent 1,055,155, March 4, 1913, Mannes and Go dowsky U. S. Patent 2,039,730, May 5, 1936, and French Patent 836,144.
- French Patent 836,144 discloses 2,5-dialkylphenols such as thymol as couplers.
- the known 2,5-dialkylphenols produce pure blue dyes with the commonly used dialkyl-p-phenylene-diamine developers and such dyes do not have the proper absorption characteristics for use in color photography. Some of the dyes produced therefrom also are objectionable in that they are readily decomposed by heat and light.
- coupler compounds have substituents in the 2- and 5-positions with respect to the phenolic hydroxyl group, one of the substituents being an alkyl or alkenyl group and the other substituent being an aminoalkyl, alkoxy, alkenyl or substituted alkenyl oup.
- the coupler compounds of our invention may be incorporated in the photographic layer prior to exposure and the colored image formed by development in a'primary aromatic amino developing solution.
- Special dispersing agents may be used for incorporating the coupler compound in the emulsion and in certain cases the coupler compound may be absorbed or adsorbed to the sensitive salt or may be combined with the sensitive silver salt; of a chemical combination.
- the coupler molecule may be suitably enlarged to render it non-diffusing in the gelatin.
- the aromatic amino developing agents used with the coupler compounds of our invention include the mono, diand tri-aminoary1 compounds and their derivatives formed by substitution in the amino group as well as in the ring such as alkyl phenylene diamines and alkyl toluylenediarnines. These compounds are usually employed in the salt form such as the hydro chloride or the sulfate which is more stable than the amines themselves. Suitable compounds are diethyl p phenylenediamine hydrochloride, monomethyl-p-phenylenediamine hydrochloride, and dimethyl-pphenylenediamine sulfate. The p-aminophenols and their substitution products may also be used Where the amino group is unsubstituted. All of these developing agent have an unsubstituted amino group at which the oxidation products of the developer couple with the color forming compounds to form dye images.
- the coupling compounds used according to our invention produce dyes which are greenish-blue in color and hence are suitable for use in three color subtractive processes of color photography. These compounds have been found to yield dyes which are more stable to heat and light than those produced from the corresponding phenols in which the -position rela tive to the hydroxyl group carries no substituent.
- the coupler used according to our invention may also have other substituents such as halogen, alkyl, etc., in other positions in the molecule as illustrated by Examples 3 to 5.
- the additional substituents illustrated in Examples 3 to 5 have not been found to confer increased stability upon the resulting dyes but may be used for purposes of altering the color of the dyes or changing their solubility and diffusion charac teristics or the solubility and diffusion characteristics of the original couplers.
- Our development process may be employed for v the production of colored photographic images in layers of gelatin or other carrier such as collodion, organic esters of cellulose, or synthetic resins.
- the carrier may be supported by a transparent medium such as glass, cellulose ester, or a non-transparent reflecting medium such as paper or an opaque cellulose ester.
- the emulsion may be coated as a single layer or as multiple layers on the support or in the case of a transparent support as superposed layers on both sides of the support.
- the superposed layers may be differentially sensitized and th dyes formed therein by coupling may be bleached by an oxidizing agent such as chromic acid to colorless soluble compounds.
- the destruction of the dye in this Way does not destroy the silver image and the silver may be resensitized to develop a color a number of times thus permitting the formation of natural color images in superposed layers as described, for example, in Mannes and Godowsky U. S. Patent 2,113,529. Colored images may also be formed in the manner described in Mannes, Godowsky and Wilder U. S. Patent 2,252,718.
- a color forming photographic developer comprising a primary aromatic amino developing agent and a phenol coupler having an alkyl substituent in one of the positions selected from the class consisting of the 2- and 5-positions with respect to the phenolic hydroxyl group and an alkenyl substituent in the other of said positions.
- A. color forming photographic developer comprising a primary aromatic amino developing agent and a phenol coupler having a methyl group in the 5-pos-ition with respect to the phenolic hydroxyl group and having an alkenyl substituent in the 2-position with respect to the phenolic hydroxyl group.
- a color forming photographic developer comprising a primary aromatic amino develop ing agent and a phenol coupler having an allyl substituent in the 2-position and an alkyl substituent in the 5-position with respect to the phenolic hydroxyl group.
- a color forming photographic developer comprising a primary aromatic amino developing agent and 2-allyl-5-methyl phenol as a coupler.
- the method of producing a colored photographic image in a gelatino silver halide emulsion layer which comprises exposing and developing it and simultaneously with the development coupling the development product of a primary aromatic amino developing agent in the presence of the developed image with a phenol coupler having an alkyl substituent in'one of the positions selected from the class consisting of the 2- and 5-positions with respect to the phenolic hydroxyl group and an alkenyl substituent in the other of said positions.
- the method of producing a colored photographic image in a gelatino silver halide emulsion layer which comprises exposing and developing it and simultaneously with the development coupling the development product of a primary aromatic amino developing agent in the presence of the developed image with a phenolic coupler compound having an allyl group in the 2-position and an alkyl group in the 5-position with respect to the phenolic hydroxyl group.
- a photographic emulsion for forming colored images comprising a carrier containing a sensitive silver halide and a phenol coupler having an alkyl substituent in one of the positions selected from the class consisting of the 2- and 5-positions With respect to the phenolic hydroxyl group and an alkenyl substituent in the other of said positions.
- a color forming photographic layer comprising a gelatino silver halide emulsion containiing a phenol coupler having an alkyl substituent in one of the positions selected from the class consisting of the 2- and 5-positions with respect to the phenolic hydroxyl group and an alkenyl substituent in the other of said positions.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR956732D FR956732A (enrdf_load_stackoverflow) | 1941-12-12 | ||
| US422699A US2338676A (en) | 1941-12-12 | 1941-12-12 | Phenolic coupler compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US422699A US2338676A (en) | 1941-12-12 | 1941-12-12 | Phenolic coupler compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2338676A true US2338676A (en) | 1944-01-04 |
Family
ID=23675978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US422699A Expired - Lifetime US2338676A (en) | 1941-12-12 | 1941-12-12 | Phenolic coupler compound |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2338676A (enrdf_load_stackoverflow) |
| FR (1) | FR956732A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2436007A (en) * | 1944-05-12 | 1948-02-17 | Ilford Ltd | Dye intermediates for colour photography |
-
0
- FR FR956732D patent/FR956732A/fr not_active Expired
-
1941
- 1941-12-12 US US422699A patent/US2338676A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2436007A (en) * | 1944-05-12 | 1948-02-17 | Ilford Ltd | Dye intermediates for colour photography |
Also Published As
| Publication number | Publication date |
|---|---|
| FR956732A (enrdf_load_stackoverflow) | 1950-02-06 |
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