US3652286A - Color photographic silver halide multi-layer material containing cyan-forming couplers - Google Patents
Color photographic silver halide multi-layer material containing cyan-forming couplers Download PDFInfo
- Publication number
- US3652286A US3652286A US22998A US3652286DA US3652286A US 3652286 A US3652286 A US 3652286A US 22998 A US22998 A US 22998A US 3652286D A US3652286D A US 3652286DA US 3652286 A US3652286 A US 3652286A
- Authority
- US
- United States
- Prior art keywords
- color photographic
- material containing
- silver halide
- layer material
- 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
Links
- 239000000463 material Substances 0.000 title abstract description 9
- -1 silver halide Chemical class 0.000 title description 3
- 229910052709 silver Inorganic materials 0.000 title description 2
- 239000004332 silver Substances 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PBAJSZZUFDEUAK-UHFFFAOYSA-N (2-chlorophenoxy) hydrogen carbonate Chemical class OC(=O)OOC1=CC=CC=C1Cl PBAJSZZUFDEUAK-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- QDOGSLSGLUTSQL-UHFFFAOYSA-N 6-amino-2,4-dichloro-3-methylphenol Chemical compound CC1=C(Cl)C=C(N)C(O)=C1Cl QDOGSLSGLUTSQL-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- HHNQGORRSUIOFR-UHFFFAOYSA-N phenoxy hydrogen carbonate Chemical class OC(=O)OOC1=CC=CC=C1 HHNQGORRSUIOFR-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000080 wetting agent 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
- G03C7/34—Couplers containing phenols
- G03C7/346—Phenolic couplers
Definitions
- ABSTRACT Color photographic material having a color coupler of the general formula B1 Cl NH-COaH-(CHEh-O wherein R is H, or a short chain alkyl; R is H, Cl, or a straightor branched chain alkyl; R is a straight or branched chain alkyl and wherein the chain carbon atoms of R and R alfi w a rsisb a l n a m is 0 1 or 1 Claims, No Drawings COLOR PHOTOGRAPHIC SILVER I'IALIDE MULTI- LAYER MATERIAL CONTAINING CYAN-FORMING COUPLERS BACKGROUND OF THE INVENTION
- the invention relates to new diffusion-proof blue-green components for the preparation of color photographic materials in accordance with the principle of the chromogeneous developing.
- the dyestuffs developed by color developing must have certain optical properties.
- a blue-green dyestuff should ideally absorb entirely red'light and allow the green as well as the blue light to penetrate as much as possible.
- a color coupler should give the highest possible color density.
- Next to the optical properties there are special requirements placed on the hydrolysis stability and the fastness of the dyestuffs. In addition, for the applicability of a color component, important is a good dispersability; also a high developing speed and with respect to the resulting dyestuff the most homogeneously dispersed color granules possible.
- the object of the invention is to find novel blue-green developers which have good properties of the named aminophenols but are less inclined to recrystallization, so that they may be employed without oil forming agents.
- R H or a short alkyl chain up to three carbon atoms; R H, chlorine or a straight or branched alkyl chain; R a straight or branched alkyl chain; the total chain length of R and R amounting up to at least eight carbon atoms; n 0, l or 2.
- the melting points of the novel couplers are relatively low
- the coupler of Formula II! has a melting point which is by ca. 15 C. lower than that of the corresponding unchlorinated couplers according to the U.S. Pat. No. 2,908,573.
- the new couplers are easily dispersed in water or gelatin solutions.
- the coupler is dissolved, for example, in a known manner in a low boiling solvent, immiscible with water, e.g., acetic ester or methylene chloride, and is then dispersed with the aid of a wetting agent in water or in gelatin solution.
- a low boiling solvent immiscible with water, e.g., acetic ester or methylene chloride
- This method is particularly suitable for the novel couplers since their solubility is preferable in the low boiling solvents.
- the use of anoil forming agent is unnecessary in most instances.
- the dispersions are stable for several days and even in storage of the finished materials there is generally no recrystallization observed. Due to this property, the novel .coupler is clearly superior to the known comparable compounds.
- the novel coupler excellent: good reactivity with all customary color developing substances and good optical properties of the formed dyestuffs.
- the obtainable color densities are particularly high which is equally traced back to the high degree of dispersion of the components.
- novel components may be employed both in the negative as well as in the reverse process. They are equally suitable for film as well as for paper materials.
- the synthesis takes place in a known manner by condensation of the aminophenol with the chlorophenoxy carbonic acids.
- Second Step Z-a-Methyltridecyl-4-chlorophenoxy acetic acid.
- 650 g. 2-a-methyltridecyl-4-chlorophenol and 490 g. chloroacetic acid ethyl ester are heated over a steam bath, then are added by drops within one hour 440 ml. of 30 percent sodium methylate solution and subsequently boiled 1 hour under reflux. Thereupon, at boiling temperature, a mixture of 550 ml. 30 percent soda lye and 550 ml. methanol is added by drops for 10-15 minutes and again restirred for 20 minutes. The reaction mixture is poured out on 4 l. water and 0.6 1.
- Couplers Of this color component 3 g. are dissolved cold in l ml. acetic ester and dispersed with 50ml. of a percent gelatin solution, which contains 4 ml. sodium dodecyl benzene sulfonate percent). The dispersion is added to a photoll] Cl' 01- NH-CO-CH-(CHzh-OQ R H3 C 1 a wherein R H or a short alkyl chain up to three carbon atoms;
- R H chlorine or a straight or branched alkyl chain
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1915948A DE1915948B2 (de) | 1969-03-28 | 1969-03-28 | Farbphotographisches Aufzeichnungsmaterial |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3652286A true US3652286A (en) | 1972-03-28 |
Family
ID=5729619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US22998A Expired - Lifetime US3652286A (en) | 1969-03-28 | 1970-03-26 | Color photographic silver halide multi-layer material containing cyan-forming couplers |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3652286A (enrdf_load_stackoverflow) |
| BE (1) | BE747782A (enrdf_load_stackoverflow) |
| DE (1) | DE1915948B2 (enrdf_load_stackoverflow) |
| FR (1) | FR2040126A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1240804A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3772002A (en) * | 1971-10-14 | 1973-11-13 | Minnesota Mining & Mfg | Phenolic couplers |
| US3941601A (en) * | 1972-03-23 | 1976-03-02 | Agfa-Gevaert, A.G. | Photographic silver halide material which contains color couplers |
| US4565777A (en) * | 1983-07-21 | 1986-01-21 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive materials |
| EP0711804A2 (de) | 1994-11-14 | 1996-05-15 | Ciba-Geigy Ag | Kryptolichtschutzmittel |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3758308A (en) * | 1971-02-18 | 1973-09-11 | Eastman Kodak Co | Silver halide emulsion containing para fluoro phenols |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2698794A (en) * | 1950-04-15 | 1955-01-04 | Eastman Kodak Co | Mixed packet photographic emulsions |
| US2908573A (en) * | 1956-07-25 | 1959-10-13 | Eastman Kodak Co | Photographic color couplers containing mono-n-alkyl groups |
-
1969
- 1969-03-28 DE DE1915948A patent/DE1915948B2/de active Granted
-
1970
- 1970-03-17 GB GB02730/70A patent/GB1240804A/en not_active Expired
- 1970-03-23 BE BE747782D patent/BE747782A/xx unknown
- 1970-03-26 US US22998A patent/US3652286A/en not_active Expired - Lifetime
- 1970-03-27 FR FR7011316A patent/FR2040126A5/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2698794A (en) * | 1950-04-15 | 1955-01-04 | Eastman Kodak Co | Mixed packet photographic emulsions |
| US2908573A (en) * | 1956-07-25 | 1959-10-13 | Eastman Kodak Co | Photographic color couplers containing mono-n-alkyl groups |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3772002A (en) * | 1971-10-14 | 1973-11-13 | Minnesota Mining & Mfg | Phenolic couplers |
| US3941601A (en) * | 1972-03-23 | 1976-03-02 | Agfa-Gevaert, A.G. | Photographic silver halide material which contains color couplers |
| US4565777A (en) * | 1983-07-21 | 1986-01-21 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive materials |
| EP0711804A2 (de) | 1994-11-14 | 1996-05-15 | Ciba-Geigy Ag | Kryptolichtschutzmittel |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1240804A (en) | 1971-07-28 |
| DE1915948C3 (enrdf_load_stackoverflow) | 1979-06-21 |
| DE1915948B2 (de) | 1978-10-19 |
| DE1915948A1 (de) | 1970-10-08 |
| FR2040126A5 (enrdf_load_stackoverflow) | 1971-01-15 |
| BE747782A (fr) | 1970-09-23 |
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