GB785334A - Improvements in or relating to cyanine dyestuffs - Google Patents
Improvements in or relating to cyanine dyestuffsInfo
- Publication number
- GB785334A GB785334A GB1487855A GB1487855A GB785334A GB 785334 A GB785334 A GB 785334A GB 1487855 A GB1487855 A GB 1487855A GB 1487855 A GB1487855 A GB 1487855A GB 785334 A GB785334 A GB 785334A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- phenyl
- group
- benzoxazole
- chloro
- 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
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- -1 ketomethylene compound Chemical class 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 150000001450 anions Chemical group 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 150000003536 tetrazoles Chemical class 0.000 abstract 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 1
- QKCKCXFWENOGER-UHFFFAOYSA-N 2-phenyloxazol-5(4H)-one Chemical compound O1C(=O)CN=C1C1=CC=CC=C1 QKCKCXFWENOGER-UHFFFAOYSA-N 0.000 abstract 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 abstract 1
- UPCYEFFISUGBRW-UHFFFAOYSA-N 3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound CCN1C(=O)CSC1=S UPCYEFFISUGBRW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 abstract 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 1
- YTSFYTDPSSFCLU-UHFFFAOYSA-N 5-chloro-1,3-benzothiazole Chemical compound ClC1=CC=C2SC=NC2=C1 YTSFYTDPSSFCLU-UHFFFAOYSA-N 0.000 abstract 1
- NIFNXGHHDAXUGO-UHFFFAOYSA-N 5-phenyl-1,3-benzoxazole Chemical compound C=1C=C2OC=NC2=CC=1C1=CC=CC=C1 NIFNXGHHDAXUGO-UHFFFAOYSA-N 0.000 abstract 1
- GFIGSHYZTSXVRD-UHFFFAOYSA-N 6-ethoxy-1,3-benzoxazole Chemical compound CCOC1=CC=C2N=COC2=C1 GFIGSHYZTSXVRD-UHFFFAOYSA-N 0.000 abstract 1
- ZLHNYIHIHQEHJQ-UHFFFAOYSA-N N,N'-Diacetylhydrazine Chemical compound CC(=O)NNC(C)=O ZLHNYIHIHQEHJQ-UHFFFAOYSA-N 0.000 abstract 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical class [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical class O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical class CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 abstract 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 125000003831 tetrazolyl group Chemical group 0.000 abstract 1
- 150000003568 thioethers Chemical group 0.000 abstract 1
- 125000005023 xylyl group Chemical group 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
- C09B23/10—The polymethine chain containing an even number of >CH- groups
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Dyes having one of the general formul <FORM:0785334/IV (b)/1> and <FORM:0785334/IV (b)/2> wherein R1 and R3 are alkyl or hydroxyalkyl groups, R2 is an alkyl, cycloalkyl, aryl or substituted aryl group, X is an anion, Z is -CH = or -N =, m and n are 0 or 1 and D1 and D2 complete heterocyclic nitrogen nuclei, are prepared by condensing a tetrazolium salt of the formula <FORM:0785334/IV (b)/3> with a compound of the formula <FORM:0785334/IV (b)/4> wherein Y is an anion and Q is a thioether, thioethervinyl or acetanilidovinyl group, or with a compound of the formula <FORM:0785334/IV (b)/5> wherein R4 is an alkyl group. In the first condensation the corresponding bases can be used with two molecular proportions of a salt R1X to give dyes wherein R1 = R3. In the second condensation a ketomethylene compound <FORM:0785334/IV (b)/6> may be used together with an alkyl orthoformic ester. In the examples, R1 and R3 are methyl or ethyl groups, R2 is methyl, phenyl, p-tolyl, xylyl, m-chlorophenyl, o-chlorophenyl, p-bromophenyl, p-methoxyphenyl and cyclohexyl, D1 completes a benzthiazole, 5-chloro-benzthiazole, benzoxazole, 5:6-dimethyl-benzoxazole, 5-phenyl - benzoxazole, 6 - ethoxy - benzoxazole, 3:3 - dimethyl - indolenine, 2 - quinoline, 4-quinoline, 4-quinazoline (Z is -N =) and 2-methylthio - 4 - pyrimidine nucleus, and D2 completes a 2:3-(benziminazo-21:11)-thiazolid4-one, 3-ethyl-rhodanine, 2-phenyl-5-oxazolone and 3 - methyl - 1 - phenyl - 5 - pyrazolone nucleus. According to the Provisional Specification, R1, R2, R3 or R4 may be an aralkyl group. Specification 425,609, [Group IV], is referred to, and 743,133 is referred to in the Provisional Specification.ALSO:The following 1-substituted-5-methyl tetrazoles are prepared from diacetyl hydrazine and the appropriately substituted or unsubstituted benzene diazonium chloride:-the 1-phenyl, 1 - p - tolyl, 1 - m - chloro, 1 - o - chloro and 1 - p - bromo derivatives. 5 - Methyl - 1 - (3 : 5-dimethylphenyl) tetrazole is prepared by treating N(3 : 5 - dimethylphenyl) acetamide with PCl5 and treating the resulting chloro-imide with hydrazoic acid. Any of the above tetrazoles as well as 1-methyl-, 1-cyclohexyl-, and 1-p-anisyl, -5-methyltetrazoles may be treated with methyl or ethyl iodides to give quaternary salts on the 4-nitrogen atom. Specification 425,609, [Group IV], is referred to and Specification 743,133 is referred to in the Provisional Specification.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL207316D NL207316A (en) | 1955-05-23 | ||
| GB1487855A GB785334A (en) | 1955-05-23 | 1955-05-23 | Improvements in or relating to cyanine dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1487855A GB785334A (en) | 1955-05-23 | 1955-05-23 | Improvements in or relating to cyanine dyestuffs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB785334A true GB785334A (en) | 1957-10-23 |
Family
ID=10049115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1487855A Expired GB785334A (en) | 1955-05-23 | 1955-05-23 | Improvements in or relating to cyanine dyestuffs |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB785334A (en) |
| NL (1) | NL207316A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3182063A (en) * | 1961-03-06 | 1965-05-04 | Warner Lambert Pharmaceutical | Substituted 4-thiazolidinones and process therefor |
| US3187002A (en) * | 1965-06-01 | Hs-chxcook |
-
0
- NL NL207316D patent/NL207316A/xx unknown
-
1955
- 1955-05-23 GB GB1487855A patent/GB785334A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3187002A (en) * | 1965-06-01 | Hs-chxcook | ||
| US3182063A (en) * | 1961-03-06 | 1965-05-04 | Warner Lambert Pharmaceutical | Substituted 4-thiazolidinones and process therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| NL207316A (en) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB893681A (en) | Improvements in dye-sensitized photographic emulsions | |
| GB785334A (en) | Improvements in or relating to cyanine dyestuffs | |
| GB1064584A (en) | Basic dyestuffs | |
| SE7703000L (en) | PROCEDURE FOR THE PREPARATION OF CARBOSTYRIL DERIVATIVES | |
| ATE32894T1 (en) | THIOMETHYLPYRIDIN DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND PHARMACEUTICALS CONTAINING THESE COMPOUNDS. | |
| ES388196A1 (en) | Imidazoline derivatives | |
| GB756226A (en) | Trinuclear polymethine dyes containing a pyrryl, indolyl or pyrrocolyl nucleus and photographic emulsions containing such dyes | |
| GB1342258A (en) | Heterocyclic compounds and their use | |
| GB760739A (en) | Process for the production of antihalation and filter layers | |
| GB1139393A (en) | 1-substituted-3,3-disubstituted-2-vinylene-3h-indoles, their preparation and their use as dyes | |
| ATE20063T1 (en) | 3-PYRIDYL-5-ALKOXY(OR PHENOXY- OR ARALKYLOXY- )PYRAZOLE DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS MEDICINAL PRODUCTS. | |
| GB620482A (en) | Trinuclear cyanine dyes and photographic light-sensitive elements containing them | |
| GB1523556A (en) | Naphthostyril dyestuffs | |
| GB1535855A (en) | Diazarhodamine-lactones their manufacture and their use as dye intermediates for copying processes | |
| GB782311A (en) | Merocyanine dyes, methods of making them and photographic emulsions containing them | |
| GB1504707A (en) | 1-aryl-2-oxo-2,4,5,6,7,7a-hexahydroindoles | |
| GB1228196A (en) | ||
| GB979045A (en) | Polymethine dyes, process of making them and photographic elements containing them | |
| GB738258A (en) | Polymethine dyes and process for preparing them | |
| GB1363718A (en) | Cyanine and merocyanine dyes | |
| EP0261602A2 (en) | Pyridine compounds and their use | |
| GB1261939A (en) | Tetrahydropyrimidines and process for preparing them | |
| IE32395B1 (en) | Benzodiazepine derivatives | |
| GB1310926A (en) | Production of dyestuffs | |
| GB903785A (en) | Improvements in or relating to the production of penicillins |