GB734793A - Improvements in or relating to polynuclear cyanine dyes - Google Patents
Improvements in or relating to polynuclear cyanine dyesInfo
- Publication number
- GB734793A GB734793A GB3023052A GB3023052A GB734793A GB 734793 A GB734793 A GB 734793A GB 3023052 A GB3023052 A GB 3023052A GB 3023052 A GB3023052 A GB 3023052A GB 734793 A GB734793 A GB 734793A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dyes
- formul
- salt
- nuclei
- quaternary
- 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
Links
- 239000000975 dye Substances 0.000 title abstract 7
- 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
- 150000003839 salts Chemical class 0.000 abstract 7
- -1 heterocyclic keto-methylene compound Chemical class 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000002585 base Substances 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- 229910017464 nitrogen compound Inorganic materials 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical compound C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 abstract 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000003367 polycyclic group Chemical group 0.000 abstract 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-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
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
-
- 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
- C09B23/0075—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring
-
- 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
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/102—The polymethine chain containing an even number of >CH- groups two heterocyclic rings linked carbon-to-carbon
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Trinuclear cyanine dyes are described which have one of the following formul <FORM:0734793/IV (c)/1> <FORM:0734793/IV (c)/2> or <FORM:0734793/IV (c)/3> wherein R1, R2, R3, R5 and R6 are alkyl groups or R1 and R2 may be aralkyl groups or may together form an aliphatic carbocyclic system such as cyclopentamethylene, R7 is a hydrocarbon group or is linked through C and N to a carbon atom in D3, X is an anion, n is 0 or 1, and D1, D2 and D3 complete 5- or 6-membered heterocyclic nuclei. The symmetrical dyes of formula I may be prepared by condensing a compound of formula <FORM:0734793/IV (c)/4> wherein R4 is an alkyl group, with at least 2 molecular proportions of a quaternary cyclammonium salt having a reactive methyl group in the presence of a base at least as strong as triethylamine. In place of the iminazolenine quaternary salt, the free base may be employed together with an equivalent of a salt R3X where R3 has the same value as R4. The unsymmetrical dyes of formula I and the dyes of formul II and III may be prepared by condensing compounds of the formul <FORM:0734793/IV (c)/5> or <FORM:0734793/IV (c)/6> with the appropriate methyl quaternary cyclammonium salt or heterocyclic keto-methylene compound, in the presence of a strong base. In place of the quaternary cyclammonium salt used in any of the above reactions, the base may be employed together with an equivalent of a salt R3X, when dyes are produced wherein R5 = R3. D1 and D2 may be the residues of thiazole, benzthiazole, benzoxazole, or benzselenazole nuclei or their polycyclic homologues, or the residues of quinoline or indolenine nuclei, any of which nuclei may be substituted in the carbocyclic rings with alkyl, aryl, alkoxy or halogen p substituents. D3 may be a residue of rhodanine, 5-pyrazolone or thiazolidones, including (with R7) 2 : 3-benziminazo-21 : 11-4-thiazolidone. Specification 734,792 is referred to. According to the Provisional Specification dyes of formul I to III and of formula <FORM:0734793/IV (c)/7> wherein R8 is hydrocarbon and D4 completes a heterocyclic nucleus, are made by reacting intermediates of formul <FORM:0734793/IV (c)/8> or <FORM:0734793/IV (c)/9> with quaternary salts of heterocyclic nitrogen compounds having a reactive methyl group or with a heterocyclic nitrogen compound having a reactive ketomethylene group. The various substituents R are defined in wider terms and additional examples of nuclei D1 to D4 are given.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3022952A GB734792A (en) | 1952-11-28 | 1952-11-28 | Improvements in or relating to cyanine dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB734793A true GB734793A (en) | 1955-08-10 |
Family
ID=10304334
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3023052A Expired GB734793A (en) | 1952-11-28 | 1952-11-28 | Improvements in or relating to polynuclear cyanine dyes |
| GB3022952A Expired GB734792A (en) | 1952-11-28 | 1952-11-28 | Improvements in or relating to cyanine dyes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3022952A Expired GB734792A (en) | 1952-11-28 | 1952-11-28 | Improvements in or relating to cyanine dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB734793A (en) |
-
1952
- 1952-11-28 GB GB3023052A patent/GB734793A/en not_active Expired
- 1952-11-28 GB GB3022952A patent/GB734792A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB734792A (en) | 1955-08-10 |
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