US3486894A - Color photographic images utilizing ureido indazolone couplers - Google Patents
Color photographic images utilizing ureido indazolone couplers Download PDFInfo
- Publication number
- US3486894A US3486894A US624203A US3486894DA US3486894A US 3486894 A US3486894 A US 3486894A US 624203 A US624203 A US 624203A US 3486894D A US3486894D A US 3486894DA US 3486894 A US3486894 A US 3486894A
- Authority
- US
- United States
- Prior art keywords
- indazolone
- ureido
- couplers
- mol
- 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
Links
- XPRRQVOHHDZKEW-UHFFFAOYSA-N (3-oxoindazol-4-yl)urea Chemical compound N(C(=O)N)C1=C2C(N=NC2=CC=C1)=O XPRRQVOHHDZKEW-UHFFFAOYSA-N 0.000 title description 10
- 239000000463 material Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000975 dye Substances 0.000 description 11
- -1 silver halide Chemical class 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- FHBWJEDOFKOWKB-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonyl-5-nitro-1H-indazol-3-one Chemical compound S(=O)(=O)(C1=CC=C(C)C=C1)N1NC2=CC=C(C=C2C1=O)[N+](=O)[O-] FHBWJEDOFKOWKB-UHFFFAOYSA-N 0.000 description 3
- GAPDJONVLUBDQT-UHFFFAOYSA-N 5-amino-2-(4-methylphenyl)sulfonyl-1H-indazol-3-one Chemical compound S(=O)(=O)(C1=CC=C(C)C=C1)N1NC2=CC=C(C=C2C1=O)N GAPDJONVLUBDQT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- LOCAIGRSOJUCTB-UHFFFAOYSA-N indazol-3-one Chemical class C1=CC=C2C(=O)N=NC2=C1 LOCAIGRSOJUCTB-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- PMAFNHPILKAJMF-UHFFFAOYSA-N 1-(3-oxoindazol-4-yl)-3-phenylurea Chemical compound C1(=CC=CC=C1)NC(NC1=C2C(N=NC2=CC=C1)=O)=O PMAFNHPILKAJMF-UHFFFAOYSA-N 0.000 description 2
- VKJGZHQYRQGMRH-UHFFFAOYSA-N 3-amino-5-(octadecanoylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC1=CC(N)=CC(C(O)=O)=C1 VKJGZHQYRQGMRH-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- HSMPSHPWCOOUJH-UHFFFAOYSA-N anilinyl Chemical compound [NH]C1=CC=CC=C1 HSMPSHPWCOOUJH-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical class O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 2
- 150000004989 p-phenylenediamines Chemical class 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AYLDJQABCMPYEN-UHFFFAOYSA-N (4-azaniumylphenyl)-diethylazanium;sulfate Chemical compound OS(O)(=O)=O.CCN(CC)C1=CC=C(N)C=C1 AYLDJQABCMPYEN-UHFFFAOYSA-N 0.000 description 1
- ZIQMWMVYTAHPJB-UHFFFAOYSA-N 1-(3-oxoindazol-5-yl)-3-phenylurea Chemical compound C1(=CC=CC=C1)NC(NC=1C=C2C(N=NC2=CC1)=O)=O ZIQMWMVYTAHPJB-UHFFFAOYSA-N 0.000 description 1
- CGGYSTYVGGSXEO-UHFFFAOYSA-N 2-carbonochloridoyl-6-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=C(Cl)C=CC=C1C(Cl)=O CGGYSTYVGGSXEO-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
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- AQPKUVRMQWPICF-UHFFFAOYSA-N 5-chloro-2-isocyanatobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(Cl)=CC=C1N=C=O AQPKUVRMQWPICF-UHFFFAOYSA-N 0.000 description 1
- RRSVLBVNRRUZKF-UHFFFAOYSA-N 5-nitroindazol-3-one Chemical compound [O-][N+](=O)C1=CC=C2N=NC(=O)C2=C1 RRSVLBVNRRUZKF-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- TVZCDRQWBLPSIC-UHFFFAOYSA-N N-(3-oxoindazol-5-yl)benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC=1C=C2C(N=NC2=CC1)=O TVZCDRQWBLPSIC-UHFFFAOYSA-N 0.000 description 1
- 150000008061 acetanilides Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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
- G03C7/3231—Couplers containing an indazolone ring
Definitions
- the present invention refers to a process for producing color photographic images by chromogenic development of a photosensitive material in the presence of color formers called couplers of the indazolone class.
- the color photography with the subtractive process is generally carried out by arranging on a support three layers of silver halide photographic emulsion, respectively sensitized to blue, green and red lights, and respectively containing couplers which, during the chromogenic development of the exposed element, react with the oxidation product of a p-phenylene diamine derivative to give yellow, magenta and cyan dyes.
- couplers which, during the chromogenic development of the exposed element, react with the oxidation product of a p-phenylene diamine derivative to give yellow, magenta and cyan dyes.
- couplers which, during the chromogenic development of the exposed element, react with the oxidation product of a p-phenylene diamine derivative to give yellow, magenta and cyan dyes.
- magenta dyes obtained during the chromogenic development, from pyrazolone couplers, have the disadvantage of having an undesired secondary absorption peak in the blue spectral region, and this is very detrimental to color purity.
- Italian Patent No. 464,564 suggests the use of indazolone derivatives as magenta couplers.
- these couplers produce dyes having favorable spectral properties, both because of the absence of undesired absorption peaks in irrelevant spectrum regions and because of a characteristic, peculiar shape of the curve in the vicinity of the main absorption peak.
- these dyes have a serious drawback, namely poor stability in the light, which shortcoming greatly reduces the possibility of their practical use.
- ureido indazolone couplers of the general formula wherein R stands for H, alkyl, aryl or a heterocyclic radical, which may contain one or more substituents to make the molecule of the coupler anti-diffusing and, if desired, alkali-soluble in accordance with the known requirements for the use of the products in color photographic processes, couples with a usual chromogenic developer of the substituted p-phenylene diamine type to produce magenta dyes which, in addition to the abovementioned desirable absorption characteristics, a high light stability, making the reliable use thereof possible in the color photography.
- the material was suspended in dilute hydrochoric acid and washed plentifully with water.
- EXAMPLE 1 A sample of a silver halide emulsion photographic material was exposed and then developed in a chromogenic developer having the following formulation:
- the developed material was washed, then processed in a bleaching bath, washed, fixed, again Washed and dried.
- a magenta-colored image was thus obtained by the formation of a dye having a main absorption peak of about 528-530 mg.
- EXAMPLE 2 By substituting in the chromogenic developer of the Example 1 for the coupler (1) an equal amount of the coupler (3,), a magenta-colored image was obtained by the formation of a dye having a main absorption peak of about 530-532 mg.
- EXAMPLE 3 12 g. of the coupler (2). were brought into solution with 20 ml. of methanol, 20 ml. of a 2 N NaOH solution and 250 ml. of water. This solution was added to one kilogram of silver halide photographic emulsion, which was then spread onto a support. The photosensitive material thus obtained was exposed and then developed by means of a diethyl-p-phenylene diamine chromogenic developer. After bleaching and fixing treatment, a magenta-colored image having a main absorption peak of about 566568 In was obtained in the exposed areas.
- EXAMPLE 4 Dyes derived from couplers Decrease in color density after exposure in iadometer after (percent)- The present The prior invention art 7 hours 30 hours 30 hours From an examination of this illustrative data it can be seen that the light storageability is significantly better for the dyes obtained from the ureido indazolone couplers of this invention.
- a process for producing light stable, color photographic images in a silver halide emulsion layer which comprises the chromogenic development of a dye by coupling with a para-phenylene diamine developer an ureido indazolone.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3122066 | 1966-03-23 | ||
| IT636566 | 1966-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3486894A true US3486894A (en) | 1969-12-30 |
Family
ID=26325781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US624203A Expired - Lifetime US3486894A (en) | 1966-03-23 | 1967-03-20 | Color photographic images utilizing ureido indazolone couplers |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3486894A (en:Method) |
| BE (1) | BE695491A (en:Method) |
| CH (1) | CH499136A (en:Method) |
| DE (1) | DE1572183A1 (en:Method) |
| GB (1) | GB1182202A (en:Method) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005028445A3 (en) * | 2003-09-19 | 2005-06-02 | Merck Sharp & Dohme | Derivatives of n-(1h-indazolyl)- and n-(1h-indolyl)-urea as well as related compounds as modulators of the vanilloid-1 receptor (vr1) for the treatment of pain |
| US20090048250A1 (en) * | 2002-10-25 | 2009-02-19 | Alex Aronov | Indazolinone compositions useful as kinase inhibitors |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2964402A (en) * | 1951-10-03 | 1960-12-13 | Gevaert Photo Prod Nv | Mono-acetyl indazolone color couplers |
| US3393071A (en) * | 1963-10-08 | 1968-07-16 | Gevaert Photo Prod Nv | Photographic color material and process utilizing 5-pyrazolone color couplers |
-
1967
- 1967-03-13 GB GB01747/67A patent/GB1182202A/en not_active Expired
- 1967-03-14 BE BE695491D patent/BE695491A/xx unknown
- 1967-03-14 CH CH373367A patent/CH499136A/it not_active IP Right Cessation
- 1967-03-14 DE DE19671572183 patent/DE1572183A1/de active Pending
- 1967-03-20 US US624203A patent/US3486894A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2964402A (en) * | 1951-10-03 | 1960-12-13 | Gevaert Photo Prod Nv | Mono-acetyl indazolone color couplers |
| US3393071A (en) * | 1963-10-08 | 1968-07-16 | Gevaert Photo Prod Nv | Photographic color material and process utilizing 5-pyrazolone color couplers |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090048250A1 (en) * | 2002-10-25 | 2009-02-19 | Alex Aronov | Indazolinone compositions useful as kinase inhibitors |
| US7842712B2 (en) | 2002-10-25 | 2010-11-30 | Vertex Pharmaceuticals Incorporated | Indazolinone compositions useful as kinase inhibitors |
| WO2005028445A3 (en) * | 2003-09-19 | 2005-06-02 | Merck Sharp & Dohme | Derivatives of n-(1h-indazolyl)- and n-(1h-indolyl)-urea as well as related compounds as modulators of the vanilloid-1 receptor (vr1) for the treatment of pain |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1182202A (en) | 1970-02-25 |
| DE1572183A1 (de) | 1970-02-19 |
| BE695491A (en:Method) | 1967-08-14 |
| CH499136A (it) | 1970-11-15 |
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