GB1485914A - Process for the preparation of 4-amino-1,8-naphthalimide compounds - Google Patents

Process for the preparation of 4-amino-1,8-naphthalimide compounds

Info

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
Application number
GB2064775A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of GB1485914A publication Critical patent/GB1485914A/en
Expired legal-status Critical Current

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

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.
GB2064775A 1974-05-15 1975-05-15 Process for the preparation of 4-amino-1,8-naphthalimide compounds Expired GB1485914A (en)

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)

* Cited by examiner, † Cited by third party
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
US20170283408A1 (en) * 2014-09-19 2017-10-05 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

Also Published As

Publication number Publication date
NL7505471A (en) 1975-11-18
JPS50159517A (en) 1975-12-24
DE2423548A1 (en) 1975-11-27
FR2271216A1 (en) 1975-12-12
CH579053A5 (en) 1976-08-31
BE829133A (en) 1975-11-17
IT1038088B (en) 1979-11-20
DE2423548C2 (en) 1984-08-23
FR2271216B1 (en) 1979-04-13

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee