GB965235A - Pyridino-anthrone dyes and dye intermediates - Google Patents
Pyridino-anthrone dyes and dye intermediatesInfo
- Publication number
- GB965235A GB965235A GB4014660A GB4014660A GB965235A GB 965235 A GB965235 A GB 965235A GB 4014660 A GB4014660 A GB 4014660A GB 4014660 A GB4014660 A GB 4014660A GB 965235 A GB965235 A GB 965235A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulpho
- chloro
- pyridino
- bromo
- alkyl
- 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
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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/14—Benz-azabenzanthrones (anthrapyridones)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises pyridino-anthrones of formula: <FORM:0965235/C1/1> wherein R1 is an alkyl radical of up to 6 carbon atoms and Z is a sulpho, chloro or bromo radical, are prepared by reacting 2-chloro-, 2-bromo- or 2-sulpho-1-amino-anthraquinone with a methyl alkyl ketone. They are used as dyestuff intermediates (see Division C4). In an example 2-chloro-1,9-(21-methyl)-pyridino-anthrone is prepared by refluxing a mixture of 1-amino-2-chloro-anthraquinone, dimethyl ketone, sodium hydroxide and water for 20-30 hours, cooling and filtering the crystalline product. The corresponding 2-bromo-, 2,4-dibromo- and 2-sulpho-compounds are also specified in examples.ALSO:The invention comprises 1.9-pyridino-anthrone compounds of formula <FORM:0965235/C4-C5/1> wherein R1 is an alkyl radical of up to 6 carbon atoms and Z is a chloro, bromo or sulpho radical or a substituted amino group -NHR wherein R is an alkyl, alkenyl or morpholino-alkyl or hydroxyalkyl radical of up to 18 carbon atoms in the alkyl chain or a cycloalkyl radical of up to 6 carbon atoms in the ring. The compounds wherein Z is an -NHR group are fluorescent yellow to orange dyes used to colour petroleum, acetate silk, nylon, polyethylene and polystyrene. The dyes are prepared by condensing a 2-chloro-, 2-bromo- or 2-sulpho-1-amino-anthraquinone with a methyl alkyl ketone to give a compound wherein Z is a chloro-, bromo-or sulpho-substituent (see Division C2) and further reacting this with an appropriate amine. In an example 2-sulpho-1,9-(21-methyl) pyridino-anthrone sodium salt is treated with aqueous hydrochloric acid to yield the acid form, n-hexylamine is added, the whole refluxed and the dye 2-n-hexylamino-1,9-(21-methyl)-pyridino-anthrone separated by cooling and filtration. Further examples are specified.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85693459A | 1959-12-03 | 1959-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB965235A true GB965235A (en) | 1964-07-29 |
Family
ID=25324805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4014660A Expired GB965235A (en) | 1959-12-03 | 1960-11-22 | Pyridino-anthrone dyes and dye intermediates |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1243302B (en) |
| GB (1) | GB965235A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4182885A (en) * | 1976-12-17 | 1980-01-08 | Dynapol | Red colors |
| US4249007A (en) | 1976-12-17 | 1981-02-03 | Dynapol | Anthraquinone colorants |
| US4279662A (en) | 1976-12-17 | 1981-07-21 | Dynapol | Polymeric red colors |
| US4316918A (en) | 1976-12-17 | 1982-02-23 | Dynapol | Products including edibles colored with polymeric red colors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE651431C (en) * | 1935-10-13 | 1937-10-18 | I G Farbenindustrie Akt Ges | Process for the preparation of compounds of the anthracene series |
| FR801416A (en) * | 1936-01-30 | 1936-08-04 | Ig Farbenindustrie Ag | Process for preparing nitrogen compounds of the anthracene series |
| DE659651C (en) * | 1936-03-27 | 1938-05-07 | I G Farbenindustrie Akt Ges | Process for the production of 2-amino-Bz, -azabenzanthronkoerpern |
-
1960
- 1960-11-22 GB GB4014660A patent/GB965235A/en not_active Expired
- 1960-12-01 DE DEO7750A patent/DE1243302B/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4182885A (en) * | 1976-12-17 | 1980-01-08 | Dynapol | Red colors |
| US4249007A (en) | 1976-12-17 | 1981-02-03 | Dynapol | Anthraquinone colorants |
| US4279662A (en) | 1976-12-17 | 1981-07-21 | Dynapol | Polymeric red colors |
| US4316918A (en) | 1976-12-17 | 1982-02-23 | Dynapol | Products including edibles colored with polymeric red colors |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1243302B (en) | 1967-06-29 |
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