UST104601I4 - Alkanediyl bridged benzimidazolo monomethine cyanine dyes, processes for their preparation, and photographic emulsions and elements containing such dyes - Google Patents
Alkanediyl bridged benzimidazolo monomethine cyanine dyes, processes for their preparation, and photographic emulsions and elements containing such dyes Download PDFInfo
- Publication number
- UST104601I4 UST104601I4 US06/570,147 US57014784A UST104601I4 US T104601 I4 UST104601 I4 US T104601I4 US 57014784 A US57014784 A US 57014784A US T104601 I4 UST104601 I4 US T104601I4
- Authority
- US
- United States
- Prior art keywords
- dyes
- benzimidazolo
- alkanediyl
- preparation
- processes
- 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.)
- Pending
Links
- 239000000975 dye Substances 0.000 title abstract 6
- 239000000839 emulsion Substances 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title abstract 2
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 150000003141 primary amines Chemical group 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 229910052709 silver Inorganic materials 0.000 abstract 1
- 239000004332 silver Substances 0.000 abstract 1
- -1 silver halide Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
-
- 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
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/08—Sensitivity-increasing substances
- G03C1/10—Organic substances
- G03C1/12—Methine and polymethine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Alkanediyl bridged benzimidazolo monomethine cyanine dyes are disclosed wherein at least one benzimidazolo nucleus is provided with an electron-withdrawing group. A disclosed preparation of the dyes includes producing an electron-withdrawing group substituted bis(2-nitrophenyl)-2-R1 -propanediamide, where R1 is hydrogen or alkyl; converting the nitro groups to primary amine substituents; removing the elements of water to effect ring closure; and thereafter providing the --CR1 -- linked benzimidazole nuclei so formed with an N,N1 -alkanediyl bridging group and quaternizing substituents. Dye synthesis is completed by reducing the --CR1 -- linking group to the corresponding methine. The dyes are useful as sensitizers in silver halide emulsions and photographic elements.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/570,147 UST104601I4 (en) | 1983-03-03 | 1984-01-12 | Alkanediyl bridged benzimidazolo monomethine cyanine dyes, processes for their preparation, and photographic emulsions and elements containing such dyes |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/471,615 US4490463A (en) | 1983-03-03 | 1983-03-03 | Alkanediyl bridged benzimidazolo monomethine cyanine dyes, processes for their preparation, and photographic emulsions and elements containing such dyes |
| US06/570,147 UST104601I4 (en) | 1983-03-03 | 1984-01-12 | Alkanediyl bridged benzimidazolo monomethine cyanine dyes, processes for their preparation, and photographic emulsions and elements containing such dyes |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/471,615 Division US4490463A (en) | 1983-03-03 | 1983-03-03 | Alkanediyl bridged benzimidazolo monomethine cyanine dyes, processes for their preparation, and photographic emulsions and elements containing such dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UST104601I4 true UST104601I4 (en) | 1984-09-04 |
Family
ID=27043506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/570,147 Pending UST104601I4 (en) | 1983-03-03 | 1984-01-12 | Alkanediyl bridged benzimidazolo monomethine cyanine dyes, processes for their preparation, and photographic emulsions and elements containing such dyes |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | UST104601I4 (en) |
-
1984
- 1984-01-12 US US06/570,147 patent/UST104601I4/en active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STPP | Information on status: patent application and granting procedure in general |
Free format text: DEFENSIVE PUBLICATION OR SIR FILE |