DE1017616B - Process for the preparation of 1, 3, 5-tri- (4-sulfamyl-phenylamino) -triazine - Google Patents

Process for the preparation of 1, 3, 5-tri- (4-sulfamyl-phenylamino) -triazine

Info

Publication number
DE1017616B
DE1017616B DEC13702A DEC0013702A DE1017616B DE 1017616 B DE1017616 B DE 1017616B DE C13702 A DEC13702 A DE C13702A DE C0013702 A DEC0013702 A DE C0013702A DE 1017616 B DE1017616 B DE 1017616B
Authority
DE
Germany
Prior art keywords
tri
triazine
sulfamyl
phenylamino
preparation
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.)
Pending
Application number
DEC13702A
Other languages
German (de)
Inventor
Dr Ernst Honold
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.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur 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 Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Priority to DEC13702A priority Critical patent/DE1017616B/en
Publication of DE1017616B publication Critical patent/DE1017616B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C07D251/70—Other substituted melamines

Description

Verfahren zur Herstellung von 1, 3, 5-Tri-(4,"-sulfamylphenylamino)-triazin Es wurde gefunden, daß man 1, 3, 5-Tri-(4'-sulfamylphenylamino)-triazin erhält, wenn man 1 Mol eines Cyanurhalogenids auf mindestens 3 Mol p-Aminobenzolsulfamid einwirken läßt.Process for the preparation of 1, 3, 5-tri- (4, "- sulfamylphenylamino) -triazine It has been found that 1, 3, 5-tri- (4'-sulfamylphenylamino) -triazine is obtained, when one mole of a cyanuric halide to at least 3 moles of p-aminobenzenesulfamide can act.

Die Reaktion wird zweckmäßig durch Erhitzen der Komponenten in einem organischen Lösungsmittel unter Zusatz eines Säure bindenden Mittels durchgeführt. Als Säure bindendes Mittel kann auch ein Überschuß an p-Aminobenzolsulfamid angewandt werden.The reaction is conveniently accomplished by heating the components in one organic solvent carried out with the addition of an acid-binding agent. An excess of p-aminobenzenesulfamide can also be used as an acid-binding agent will.

Das so erhaltene 1, 3, 5-Tri-(4'-sulfamyl-phenylamino)-triazin entspricht der Formel: Es löst sich leicht in Alkalien auf. Aus Dimethylformamid, verdünnt mit Methanol und Wasser, läßt es sich umkristallisieren. Bei etwa 339° zersetzt es sich. Es zeigt ein starkes selektives Lichtabsorptionsvermögen mit einem Maximum bei 290 bis 310 mp., d. h. in einem Wellenbereich, in dem auch die Erythemkurve ein scharfes Maximum aufweist (s. »Taschenbuch für Chemiker und Physiker« von jean D'Ans und Ellen Lax, Berlin 1943, S. 1168 unten). Man kann es deshalb vorteilhaft als Lichtschutzmittel verwenden.The 1, 3, 5-tri- (4'-sulfamyl-phenylamino) -triazine thus obtained corresponds to the formula: It dissolves easily in alkalis. It can be recrystallized from dimethylformamide, diluted with methanol and water. It decomposes at around 339 °. It shows a strong selective light absorption capacity with a maximum at 290 to 310 mp., Ie in a wave range in which the erythema curve also has a sharp maximum (see "Taschenbuch für Chemiker und Physiker" by Jean D'Ans and Ellen Lax, Berlin 1943, p. 1168 below). It can therefore be used advantageously as a light stabilizer.

Die Ausmessung der Absorptionskurve ergab für die Substanz der Erfindung im Bereich von 300 m#t eine Extinktion vom Wert 200, während das als Lichtschutzmittel bekannte Sulfanilanilid der Formel (s. Archiv für Dermatologie, Bd. 200, S. 80 unter Nr. 2) im gleichen Bereich nur eine Extinktion von etwa 20 zeigt. Zu einer Lösung von 184 g Cyanurchlorid in 1000 ccm Toluol gibt man 1100 g 4-Aminobenzolsulfamid in feingepulverter Form und läßt bei Zimmertemperatur etwa 12 Stunden rühren. Hierauf wird noch 12 Stunden rückfließend gekocht. Das Kondensationsprodukt wird abgesaugt, mit Toluol gewaschen, mit Wasserdampf behandelt und mit heißem Wasser ausgewaschen. Zur Reinigung wird das so erhaltene 1, 3, 5-Tri- (4'-sulfamyl-phenylamino)-triazin als Natronsalz gelöst und mit Säure gefällt.The measurement of the absorption curve gave an extinction of 200 for the substance of the invention in the range of 300 m # t, while the sulfanilanilide of the formula, known as a light stabilizer (see Archives for Dermatology, Vol. 200, p. 80 under No. 2) shows only an absorbance of about 20 in the same range. 1100 g of 4-aminobenzenesulfamide in finely powdered form are added to a solution of 184 g of cyanuric chloride in 1000 cc of toluene and the mixture is stirred at room temperature for about 12 hours. It is then refluxed for a further 12 hours. The condensation product is filtered off with suction, washed with toluene, treated with steam and washed out with hot water. For purification, the 1, 3, 5-tri- (4'-sulfamyl-phenylamino) -triazine obtained in this way is dissolved as the sodium salt and precipitated with acid.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 1, 3, 5-Tri-(4'-sulfamyl-phenylamino)-triazin, dadurch gekennzeichnet, daß man 1 Mol eines Cyanurhalogenids auf mindestens 3 Mol p-Aminobenzolsulfamid einwirken läßt. In Betracht gezogene Druckschriften: Deutsche Patentschrift Nr. 750 400.PATENT CLAIM: Process for the production of 1, 3, 5-tri- (4'-sulfamyl-phenylamino) -triazine, characterized in that 1 mol of a cyanuric halide to at least 3 mol Allow p-aminobenzene sulfamide to act. Publications considered: German Patent No. 750 400.
DEC13702A 1956-09-20 1956-09-20 Process for the preparation of 1, 3, 5-tri- (4-sulfamyl-phenylamino) -triazine Pending DE1017616B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC13702A DE1017616B (en) 1956-09-20 1956-09-20 Process for the preparation of 1, 3, 5-tri- (4-sulfamyl-phenylamino) -triazine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC13702A DE1017616B (en) 1956-09-20 1956-09-20 Process for the preparation of 1, 3, 5-tri- (4-sulfamyl-phenylamino) -triazine

Publications (1)

Publication Number Publication Date
DE1017616B true DE1017616B (en) 1957-10-17

Family

ID=7015495

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC13702A Pending DE1017616B (en) 1956-09-20 1956-09-20 Process for the preparation of 1, 3, 5-tri- (4-sulfamyl-phenylamino) -triazine

Country Status (1)

Country Link
DE (1) DE1017616B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3061605A (en) * 1960-01-18 1962-10-30 Dal Mon Research Co (amino-benzenesulfonylamino)-s-triazine derivatives
EP0087098A2 (en) * 1982-02-23 1983-08-31 BASF Aktiengesellschaft s-Triazine derivatives and their use as sunscreen agents
EP0140062A1 (en) * 1983-09-16 1985-05-08 Hoechst Aktiengesellschaft Perfluoroalkyl anthranilates, processes for their preparation and their use as dirt-repelling agents
EP0818450A1 (en) * 1996-07-08 1998-01-14 Ciba SC Holding AG Triazine derivatives as UV filter in sunscreen products

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE750400C (en) * 1938-03-26 1953-04-16 Hydrierwerke A G Deutsche Process for the production of condensation products

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE750400C (en) * 1938-03-26 1953-04-16 Hydrierwerke A G Deutsche Process for the production of condensation products

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3061605A (en) * 1960-01-18 1962-10-30 Dal Mon Research Co (amino-benzenesulfonylamino)-s-triazine derivatives
EP0087098A2 (en) * 1982-02-23 1983-08-31 BASF Aktiengesellschaft s-Triazine derivatives and their use as sunscreen agents
EP0087098A3 (en) * 1982-02-23 1984-12-05 Basf Aktiengesellschaft S-triazine derivatives and their use as sunscreen agents
EP0140062A1 (en) * 1983-09-16 1985-05-08 Hoechst Aktiengesellschaft Perfluoroalkyl anthranilates, processes for their preparation and their use as dirt-repelling agents
EP0818450A1 (en) * 1996-07-08 1998-01-14 Ciba SC Holding AG Triazine derivatives as UV filter in sunscreen products
US6193960B1 (en) 1996-07-08 2001-02-27 Ciba Specialty Chemicals Corporation Triazine derivatives
EP1293504A2 (en) * 1996-07-08 2003-03-19 Ciba SC Holding AG Triazine derivatives as UV-filter in cosmetic compositions

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