DE576614C - Process for the preparation of copper-containing disazo dyes - Google Patents

Process for the preparation of copper-containing disazo dyes

Info

Publication number
DE576614C
DE576614C DEI40360D DEI0040360D DE576614C DE 576614 C DE576614 C DE 576614C DE I40360 D DEI40360 D DE I40360D DE I0040360 D DEI0040360 D DE I0040360D DE 576614 C DE576614 C DE 576614C
Authority
DE
Germany
Prior art keywords
copper
amino
disazo dyes
acid
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.)
Expired
Application number
DEI40360D
Other languages
German (de)
Inventor
Dr Heinrich Clingestein
Dr Karl Wiedemann
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI40360D priority Critical patent/DE576614C/en
Application granted granted Critical
Publication of DE576614C publication Critical patent/DE576614C/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00Complex metal compounds of azo dyes
    • C09B45/01Complex metal compounds of azo dyes characterised by the method of metallisation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

Verfahren zur Darstellung kupferhaltiger Disazofarbstoffe Es wurde gefunden, daß. man zu wertvollen, sehr lichtechten, substantiven kupferhaltigen Disazofarbstoffen gelangt, wenn man Disazofarbstoffe, die durch Kuppeln eines tetrazotierten aromatischen Diamins, welches in o-Stellung zu jeder Aminogruppe eine Alkoxygruppe enthält, mit 2 Mol 2-Amino-5-oxynaphthalin-i - 2-disulfons,äure bzw. einer N-Acylverbindung hiervon oder mit i Mol i-Amino-5-oxynaphthalin-i # 7-@disulfons,äure bzw. einer 1V-Acylverbindung hiervon und I Mol einer Oxynaphthalinsulfonsäure in alkalischer Lösung erhältlich sind; in Substanz mit kupferabgebenden Mitteln behandelt.Process for the preparation of copper-containing disazo dyes Es was found that. one to valuable, very lightfast, substantive ones containing copper Disazo dyestuffs are obtained when one disazo dyestuffs are obtained by coupling a tetrazotized aromatic diamine, which is an alkoxy group in o-position to each amino group contains, with 2 moles of 2-amino-5-oxynaphthalene-i - 2-disulfonic acid or an N-acyl compound of these or with i mole of i-amino-5-oxynaphthalene-i # 7- @ disulfonic acid or one 1V acyl compound thereof and 1 mole of an oxynaphthalenesulfonic acid in alkaline Solution are available; treated in substance with copper-releasing agents.

Diese neuen kupferhaltigen Farbstoffe färben Baumwolle, Seeide und Kunstseide aus regenerierter Gellulose in sehr lichtechten violetten bis blauen Tönen. Beispiel i 244 Gewichtsteile 4 . 4'-Diamino-3 # 3'-dimethoxydiphenyl werden tetrazotiert und sodaalkalisch mit 758 Gewichtsteilen 2-AcetylamÜno-5-oxynaphthalin-i # 7-disulfons,äure gekuppelt. Der isolierte Farbstoff wird in etwa 3o ooo Gewichtsteilen kalkfreiem Wasser angerührt, die Suspension vorübergehend angesäuert und dann 2 Stunden bei 75 bis 80° C mit einer ständig ammoniakalisch gehaltenen Lösung von 5oo Gewichtsteilen kristallisiertem Kupfersulfat in 2ooo Gewichtsteilen Wasser behandelt. Der mit wenig Salz isolierte Farbstoff stellt getrocknet ein dunkles Pulver dar, das sich in Wasser mit blauer Farbe löst und- Baumwolle, Seide und Kunstseide aus regenerierter Cellulose sehr lichtecht rotstichigblau färbt. Beispiel 2. 244 Gewichtsteile 4 . 4'-Diamino-3 . 31-dimethoxydiphenyl werden tetrazotiert und schwach sodaalkalisch mit 31g Gewichtsteilen 2-Amino-5-.oxynaplhthalin-i # 7-,disulfonsäure bis zum Verschwinden der Reaktion auf freie Tetrazoverbindung gekuppelt, und der so gebildete Zwischenkärper wird in stärker sodaalkalischem Medium mit 224 Gewichtsteilen i-Oxynaphthalin-4-sulfonsäure zum Disazofarbstoff vereinigt. Der isolierte Farbstoff wird nun, wie im Beispiel i angegeben, mit 5oo Gewichtsteilen kristallisiertem Kupfersulfat ammoniakalisch behandelt. Der -Farbstoff löst sich in Wasser mit blauer Farbe und färbt Baumwolle in sehr lichtechten rotstichigblauen Tönen. B.eispi-el 3 3o2 Gewichtsteile 4 # 4'-Diamino-3 # 3'-chmethoxydiphenylharnstoff werden tetrazotiiert und soloalkalisch mit 758 Gewichtsteilen 2-Acetylamino-5-oxynaphthalin-i # 7-äisulfons.äure gekuppelt und der isolierte Farbstoff, wie im Beispiel i angegeben, mit 5oo Gewichtsteilen kristallisiertem Kupfersulfat ammoniakalisch gekupfert. Der isolierte und getrocknete Farbstoff löst sich in Wasser violett und färbt Baumwolle in sehr - lichtechten und bügelechten blaustichigvioletten Tönen.These new copper-containing dyes dye cotton, silk and Artificial silk made from regenerated gelulose in very lightfast purple to blue Tones. Example i 244 parts by weight 4. 4'-diamino-3 # 3'-dimethoxydiphenyl tetrazotized and soda-alkaline with 758 parts by weight of 2-AcetylamÜno-5-oxynaphthalene-i # 7-disulfons, acid coupled. The isolated dye is in about 30,000 parts by weight lime-free water, temporarily acidified the suspension and then 2 Hours at 75 to 80 ° C with a constantly ammoniacal solution of Treated 5oo parts by weight of crystallized copper sulfate in 2ooo parts by weight of water. The dye, isolated with a little salt, is a dark powder when dried, which dissolves in water with a blue color and - cotton, silk and rayon regenerated cellulose gives a very lightfast reddish-tinged blue color. Example 2. 244 parts by weight 4th 4'-diamino-3. 31-dimethoxydiphenyl are tetrazotized and slightly alkaline to soda with 31g parts by weight of 2-amino-5-oxynaplhthalene-i # 7-, disulfonic acid until it disappears coupled to the reaction to free tetrazo compound, and the intermediate body thus formed is in a stronger soda-alkaline medium with 224 parts by weight of i-oxynaphthalene-4-sulfonic acid combined to form the disazo dye. The isolated dye is now, as in the example i stated, with 500 parts by weight of crystallized copper sulfate ammoniacal treated. The dye dissolves in water with a blue color and stains cotton in very lightfast reddish blue tones. For example, 3 3o2 parts by weight of 4 # 4'-diamino-3 # 3'-methoxydiphenylureas are tetrazotized and solo alkaline coupled with 758 parts by weight of 2-acetylamino-5-oxynaphthalene-i # 7-isulphonic acid and the isolated dye, as indicated in Example i, with 500 parts by weight crystallized copper sulfate ammoniacally coppered. The isolated and dried Dye dissolves violet in water and dyes cotton very lightfast and iron-resistant bluish purple tones.

Der gleiche Farbstoff kann auch erhalten werden, wenn i Mol 5-Nitro-2-amino-i-anisol diazotiert und mit i Mo1 2-Acetylamino-5-oxynaphthalin-i # 7-disulfons.äure gekuppelt, dann mit Schwefelnatrium zum Aminoazofarbstoffreduziert, dieser phosgeniert und schließlich gekupfert wird.The same dye can also be obtained if i mole of 5-nitro-2-amino-i-anisole diazotized and coupled with i Mo1 2-acetylamino-5-oxynaphthalene-i # 7-disulfonic acid, then reduced with sodium sulphide to the aminoazo dye, this phosgenated and will eventually be copied.

Claims (1)

PATLNI:ANSPR.UCB.: Verfahren zur Darstellung kupferhaltiger DisazofarbstofFe, dadurch gekennzeichnet, daß Disazofarbstoffe, die durch Kuppeln der Tetrazoverbindung eines aromatischen Diamins, welches in o-Stellung -zu jeder Aminogruppe eine Alkoxygruppe enthält, mit 2 Mol 2-Arnino-5-oxynaphthalin-1 . 7-disulfonsäure bzw. -ein-er N-Acylverbindung hiervon oder mit 1 M01 2-Amino-5 - oxynaphthalin - 1 # 7 - disulfons:äure bzw. ,einer N-Acylverbindung hiervon und i Mol einer Oxynaphthalinsulfonsäure in alkalischer Lösung erhältlich sind, in Substanz mit kupferabgebenden Mitteln behandelt werden.PATLNI: ANSPR.UCB .: Process for the preparation of copper-containing disazo dyes, characterized in that disazo dyes obtained by coupling the tetrazo compound an aromatic diamine which is an alkoxy group in o-position to each amino group contains, with 2 moles of 2-amino-5-oxynaphthalene-1. 7-disulfonic acid or an N-acyl compound of these or with 1 M01 2-amino-5 - oxynaphthalene - 1 # 7 - disulfonic: acid or, one N-acyl compound thereof and 1 mole of an oxynaphthalenesulfonic acid in alkaline Solution available, can be treated in substance with copper-donating agents.
DEI40360D 1931-01-10 1931-01-10 Process for the preparation of copper-containing disazo dyes Expired DE576614C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI40360D DE576614C (en) 1931-01-10 1931-01-10 Process for the preparation of copper-containing disazo dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI40360D DE576614C (en) 1931-01-10 1931-01-10 Process for the preparation of copper-containing disazo dyes

Publications (1)

Publication Number Publication Date
DE576614C true DE576614C (en) 1933-05-16

Family

ID=7190284

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI40360D Expired DE576614C (en) 1931-01-10 1931-01-10 Process for the preparation of copper-containing disazo dyes

Country Status (1)

Country Link
DE (1) DE576614C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE915603C (en) * 1951-02-07 1954-07-26 Geigy Ag J R Process for the preparation of copper-containing disazo dyes
DE951948C (en) * 1954-07-04 1956-11-08 Bayer Ag Process for the preparation of disazo dyes
DE1012405B (en) * 1955-03-18 1957-07-18 Sandoz Ag Process for the preparation of copper-containing disazo dyes

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE915603C (en) * 1951-02-07 1954-07-26 Geigy Ag J R Process for the preparation of copper-containing disazo dyes
DE951948C (en) * 1954-07-04 1956-11-08 Bayer Ag Process for the preparation of disazo dyes
DE1012405B (en) * 1955-03-18 1957-07-18 Sandoz Ag Process for the preparation of copper-containing disazo dyes

Similar Documents

Publication Publication Date Title
AT162946B (en) Process for the preparation of new copper-compatible polyazo dyes
DE576614C (en) Process for the preparation of copper-containing disazo dyes
DE1046220B (en) Process for the production of monoazo dyes and their metal complex compounds
DE616676C (en) Process for the preparation of copper-containing disazo dyes
DE577165C (en) Process for the preparation of polyazo dyes
DE477061C (en) Process for the preparation of related trisazo dyes
DE880376C (en) Process for the preparation of copper-containing disazo dyes
DE677663C (en) Process for the production of azo dyes
DE850042C (en) Process for the production of copper-containing trisazo dyes
DE603835C (en) Process for the production of azo dyes
AT162229B (en) Process for the production of copper-containing azo dyes
DE659893C (en) Process for the preparation of copper-containing tetrakisazo dyes
DE592087C (en) Process for the production of metal-containing dyes for vegetable fibers
DE548614C (en) Process for the preparation of trisazo dyes
DE704926C (en) Process for the production of disazo and trisazo dyes
AT123394B (en) Process for the preparation of substantively coloring copper-containing o-carboxyazo dyes.
DE921225C (en) Process for the preparation of disazo dyes
DE467060C (en) Process for the preparation of a black trisazo dye
CH391149A (en) Process for the preparation of new disazo dyes
DE1079760B (en) Process for the production of azo dyes
CH174539A (en) Process for the preparation of a trisazo dye.
CH289588A (en) Process for the preparation of a polyazo dye.
CH318449A (en) Process for the preparation of metal-containing tetrakisazo dyes
CH325840A (en) Process for the preparation of new disazo dyes
CH275801A (en) Process for the preparation of a metallizable monoazo dye.