GB1485914A - Process for the preparation of 4-amino-1,8-naphthalimide compounds - Google Patents
Process for the preparation of 4-amino-1,8-naphthalimide compoundsInfo
- Publication number
- GB1485914A GB1485914A GB2064775A GB2064775A GB1485914A GB 1485914 A GB1485914 A GB 1485914A GB 2064775 A GB2064775 A GB 2064775A GB 2064775 A GB2064775 A GB 2064775A GB 1485914 A GB1485914 A GB 1485914A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- primary amine
- reaction
- hydrazine
- halo
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/0004—General aspects of dyeing
- D06P1/0012—Effecting dyeing to obtain luminescent or phosphorescent dyeings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1485914 Preparing 4-amino-1,8-naphthalimides HOECHST AG 15 May 1975 [15 May 1974] 20647/75 Heading C4P Compounds of the general formula wherein R is an optionally substituted amino group or an aliphatic, isocyclic or heterocyclic radical of a primary amine (RNH 2 ) having a pKa value (at 25‹ C.) of at least 8 and X is H or a sulphonic acid group are prepared by reacting 1 mol of a 4-halo-1,8-naphthalic acid anhydride with 1 mol of hydrazine or of a primary amine RNH 2 having a pKa-value of at least 8 and then reacting the 4-halo-1,8- naphthalic acid imide formed with ammonia and if necessary sulphonating the product when X is H. The reaction with the hydrazine or primary amine takes place at 50-150‹ C. preferably in presence of a polar solvent, e.g. water, glacial acetic acid or an aprotic solvent, e.g. dimethyl sulphoxide, N-methyl pyrrolidone, hexamethylphosphoric acid trisamide, dimethyl formamide or dimethylacetamide. The reaction with ammonia takes place at 150-180‹ C. in presence of water or an aliphatic alcohol, or mixtures thereof and the sulphonation reaction is carried out using chlorosulphonic acid or forming sulphuric acid preferably containing 5-20% sulphur trioxide at up to 50‹ C. The dyes are used to dye or print polyacrylonitrile and copolymers of acrylonitrile with vinyl compounds, block copolymers of acrylonitrile with polyurethanes, polypropylene or cellulose 2¢ and 3-acetates, polyesters and polyamides and are also used to colour plastics, resins, oils, waxes, paper, paints, lacquers, for spin dyeing polyacrylonitrile and the preparation of daylight fluorescent pigments.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19742423548 DE2423548C2 (en) | 1974-05-15 | 1974-05-15 | Process for the preparation of 4-amino1,8-naphthalimide compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1485914A true GB1485914A (en) | 1977-09-14 |
Family
ID=5915615
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2064775A Expired GB1485914A (en) | 1974-05-15 | 1975-05-15 | Process for the preparation of 4-amino-1,8-naphthalimide compounds |
Country Status (8)
Country | Link |
---|---|
JP (1) | JPS50159517A (en) |
BE (1) | BE829133A (en) |
CH (1) | CH579053A5 (en) |
DE (1) | DE2423548C2 (en) |
FR (1) | FR2271216B1 (en) |
GB (1) | GB1485914A (en) |
IT (1) | IT1038088B (en) |
NL (1) | NL7505471A (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES459497A1 (en) * | 1977-06-04 | 1978-04-16 | Made Labor Sa | N(Aminoalkyl)-naphthalimides and their derivatives |
DE3614414A1 (en) * | 1986-04-29 | 1987-11-05 | Knoll Ag | NEW BENZO (DE) ISOCHINOLIN-1,3-DIONE, THEIR PRODUCTION AND USE |
DE102004006142A1 (en) * | 2004-02-07 | 2005-08-25 | Wella Ag | Neutral and cationic naphthalene derivatives and colorants for keratin fibers containing these compounds |
WO2016041511A1 (en) * | 2014-09-19 | 2016-03-24 | Yen-Ta Lu | Benzo-heterocyclic compounds and their applications |
CN113717104B (en) * | 2021-08-06 | 2024-01-02 | 盐城东吴化工有限公司 | Preparation and application of leveling cationic fluorescent dye containing long carbon chain |
CN113831286B (en) * | 2021-09-16 | 2023-02-28 | 东华大学 | Gemini type naphthalimide cationic fluorescent dye and preparation method thereof |
-
1974
- 1974-05-15 DE DE19742423548 patent/DE2423548C2/en not_active Expired
-
1975
- 1975-05-09 NL NL7505471A patent/NL7505471A/en unknown
- 1975-05-12 CH CH607875A patent/CH579053A5/xx not_active IP Right Cessation
- 1975-05-13 IT IT2329075A patent/IT1038088B/en active
- 1975-05-14 JP JP5718575A patent/JPS50159517A/ja active Pending
- 1975-05-15 FR FR7515143A patent/FR2271216B1/fr not_active Expired
- 1975-05-15 GB GB2064775A patent/GB1485914A/en not_active Expired
- 1975-05-15 BE BE156401A patent/BE829133A/en unknown
Also Published As
Publication number | Publication date |
---|---|
DE2423548A1 (en) | 1975-11-27 |
FR2271216B1 (en) | 1979-04-13 |
BE829133A (en) | 1975-11-17 |
FR2271216A1 (en) | 1975-12-12 |
IT1038088B (en) | 1979-11-20 |
CH579053A5 (en) | 1976-08-31 |
JPS50159517A (en) | 1975-12-24 |
NL7505471A (en) | 1975-11-18 |
DE2423548C2 (en) | 1984-08-23 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |