DE1932826A1 - Azo dye and process for its preparation - Google Patents

Azo dye and process for its preparation

Info

Publication number
DE1932826A1
DE1932826A1 DE19691932826 DE1932826A DE1932826A1 DE 1932826 A1 DE1932826 A1 DE 1932826A1 DE 19691932826 DE19691932826 DE 19691932826 DE 1932826 A DE1932826 A DE 1932826A DE 1932826 A1 DE1932826 A1 DE 1932826A1
Authority
DE
Germany
Prior art keywords
parts
dye
volume
weight
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
DE19691932826
Other languages
German (de)
Inventor
Manz Dr-Chem Gottfried
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Priority to DE19691932826 priority Critical patent/DE1932826A1/en
Priority to CH926770A priority patent/CH501706A/en
Priority to NL7009298A priority patent/NL7009298A/xx
Priority to BR21998170A priority patent/BR7019981D0/en
Priority to BE752517D priority patent/BE752517A/en
Priority to FR7023758A priority patent/FR2048017A7/fr
Priority to GB1251319D priority patent/GB1251319A/en
Publication of DE1932826A1 publication Critical patent/DE1932826A1/en
Pending legal-status Critical Current

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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/06—Preparation of azo dyes from other azo compounds by oxidation
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/28—Colorants ; Pigments or opacifying agents

Landscapes

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

Description

FARBENFABRIKEN BAYER AGFARBENFABRIKEN BAYER AG LEVERKUSEN.i»y«weA 2 7, JURI 1969LEVERKUSEN.i "y" weA 2 7, JURI 1969 Patent-AbteilungPatent department

Ut/RuUt / Ru

Azofarbstoff und Verfahren zu dessen HerstellungAzo dye and process for its preparation

Die Erfindung betrifft einen wertvollen neuen Azofarbstoff der FormelThe invention relates to a valuable new azo dye of the formula

Man erhält diesen Farbstoff, wenn man den Aminoazofarbstoff der FormelThis dye is obtained by using the aminoazo dye the formula

NH,NH,

CH=CCH = C

SO,H HO 5SO, H HO 5

N=N-Y' VWN=NN = N-Y 'VWN = N

(ID(ID

in an sich bekannter Weise triazoliert.triazolized in a known manner.

Die Triazolierung des o-Aminoazofarbstoffes erfolgt in an sich bekannter Weise in wäßrigem Medium mit Kupfersulfat in Gegenwart von Ammoniak oder Essigsäure bei erhöhter Temperatur, vorzugsweise im Temperaturbereich 80 bis 1000C.The triazolation of the o-aminoazo dye is carried out in a manner known per se in an aqueous medium with copper sulfate in the presence of ammonia or acetic acid at an elevated temperature, preferably in the temperature range 80 to 100 ° C.

Le A 12Le A 12

00 9 883/180300 9 883/1803

- Der Ausgangsfarbstoff der Formel (II) wird erhalten durch Kupplung der Diazoverbindung des Amins der Formel- The starting dye of the formula (II) is obtained by Coupling of the diazo compound of the amine of the formula

H=CHH = CH

SO3H HO,SO 3 H HO,

(III)(III)

mit 2-with 2-

Der neue Farbstoff eignet sich vorzüglich zum Färben von Cellulosematerialien, insbesondere von Papier, und ergibt Färbungen von sehr guten Echtheitseigenschaften. Der neue Farbstoff zeigt hervorragende Löslichkeit in Wasser und ermöglicht, Farbstofflösungen von sehr hoher Konzentration (mindestens 20 %) herzustellen, die bei Lagerung in der Kälte keine Farbstoffabscheidung zeigen. Beispiel;The new dye is particularly suitable for dyeing cellulose materials, in particular paper, and produces dyeings with very good fastness properties. The new dye shows excellent solubility in water and enables dye solutions of very high concentration (at least 20 %) to be prepared which do not show any dye separation when stored in the cold. Example ;

60,2 Gewichtsteile des Aminostilbentriazols, das durch Kuppeln von diazotierter 4-Nitro-4'-aminostilben-2,21-disulfonsäure auf 2-Aminonaphthalin-i-sulfonsäure, Triazolierung der o-Aminoazoverbindung und Reduktion der Nitrogruppe zur Aminogruppe in bekannter Weise hergestellt ist, werden in 400 Volumteilen Wasser bei 8O0C neutral gelöst und mit 6,9 Gewichtsteilen Natriumnitrit versetzt. Die Lösung läßt man unter Rühren zu einem Gemisch aus 32 Volumteilen Salzsäure (d 1,14), 200 Volumteilen Wasser und 250 Gewichtsteilen Eis zulaufen. Nach beendeter Diazotierung gibt man eine Lösung von 10,7 Gewichtsteilen l-Amino-3-methylbenzol in 12,5 Volumteilen Salzsäure (d 1,14) und 100 Volumteilen Wasser hinzu, wobei anschließend mit 97,5 Volumteilen Natriumacetatlösung 20 Jig abgepuffert wird. Nach beendeter Kupplung wird die Zwischenstufe kongosauer isoliert. Die so erhaltene Zwischenverbindung wird in 600 Volumteilen Wasser schwach natronalkalisch gelöst und mit 6,9 Gewichtsteilen Natriumnitrit versetzt. Die Lösung läßt man unter60.2 parts by weight of the aminostilbene triazole obtained by coupling diazotized 4-nitro-4'-aminostilbene-2,2 1 -disulfonic acid to 2-aminonaphthalene-i-sulfonic acid, triazolation of the o-aminoazo compound and reduction of the nitro group to the amino group in a known manner is made, are dissolved neutral at 8O 0 C and treated with 6.9 parts by weight of sodium nitrite in 400 parts by volume. The solution is allowed to run into a mixture of 32 parts by volume of hydrochloric acid (d 1.14), 200 parts by volume of water and 250 parts by weight of ice, with stirring. When the diazotization is complete, a solution of 10.7 parts by weight of 1-amino-3-methylbenzene in 12.5 parts by volume of hydrochloric acid (d 1.14) and 100 parts by volume of water is added, 20 jig then being buffered with 97.5 parts by volume of sodium acetate solution. After the coupling has ended, the intermediate stage is isolated in a Congo acidic manner. The intermediate compound obtained in this way is dissolved in 600 parts by volume of water using a weak sodium hydroxide solution, and 6.9 parts by weight of sodium nitrite are added. The solution is left underneath

Lc A 12 344Lc A 12 344

-2 --2 -

009883/1803009883/1803

Rühren zu einem Gemisch von 120 Volumteilen Waseer, 49 Volumteilen Salzsäure (d 1,14) und 240 Gewichtsteilen Eis zulaufen. Nach beendeter Diazotierung wird mit einer Lösung von 24,5 Gewichtsteilen 2-Aminonaphthalin-6-sulfonsäure in 632 Volumteilen Wasser und 10,3 Volumteilen 40 jSiger wäßriger Natronlauge unter Zusatz von 200 Gewichtsteilen Eis, 20 Gewichtsteilen Natriumbicarbonat und 26,5 Gewichtsteilen Natriumacetat gekuppelt. Die erhaltene Kupplungslösung wird auf 800C erwärmt, mit 68 Volumteilen 25 iigem Ammoniakwasser und anschließend mit 50 Gewichtsteilen kristallisiertem Kupfersulfat versetzt und bis zur Beendigung der Triazolierung gekocht. Nach Abtrennen des Kupfer-I-oxyds durch Filtration - gegebenenfalls nach Austreiben des Ammoniaküberschusses und Zugabe von 43 Volumteilen 40 JCiger wäßriger Natronlauge sowie unter Zusatz von Tierkohle (Aktivkohle) - wird aus dem Piltrat der Parbstoff mit Natriumchlorid abgeschieden und isoliert. Der erhaltene Farbstoff entspricht in Form der freien Säure der FormelStir to a mixture of 120 parts by volume of Waseer, 49 parts by volume of hydrochloric acid (d 1.14) and 240 parts by weight of ice. When the diazotization is complete, the mixture is coupled with a solution of 24.5 parts by weight of 2-aminonaphthalene-6-sulfonic acid in 632 parts by volume of water and 10.3 parts by volume of 40% aqueous sodium hydroxide solution with the addition of 200 parts by weight of ice, 20 parts by weight of sodium bicarbonate and 26.5 parts by weight of sodium acetate. The coupling solution is heated to 80 0 C, added with 68 parts by volume of 25 iigem ammonia water, and then crystallized with 50 parts by weight copper sulfate and until completion of the Triazolierung cooked. After the copper (I) oxide has been separated off by filtration - if necessary after expelling the excess ammonia and adding 43 parts by volume of 40% aqueous sodium hydroxide solution and adding animal charcoal (activated charcoal) - the paraffin is separated from the piltrate with sodium chloride and isolated. The dye obtained corresponds to the formula in the form of the free acid

CH*CH *

0,H HO,S0, H HO, S

Er stellt in getrockneter Form ein gelbbraunes Pulver dar, das sich sehr leicht in Wasser mit gelber Färbe löst und Baumwolle und Papier in gelben Tönen färbt.In dried form, it is a yellow-brown powder that dissolves very easily in water with yellow dye and cotton and stains paper in yellow tones.

Die Schließung des zweiten Triazolringes kann auch erfolgen durch Zugabe von 50 Gewichtsteilen kristallisiertem Kupfersulfat zu der auf 800C aufgeheizten Kupplungslösung und anschließendes einstündiges Kochen. Das Kupfer-I-oxyd wird nach Zugabe von 41,5 Gewichtsteilen Natriumcarbonat - gegebenenfalls unter Zusatz von Aktivkohle und Kieselgur - durch Filtration abgetrennt. Der Farbstoff wird mit Natriumchlorid ausgesalzen und isoliert.The closure of the second triazole ring can also be made by adding 50 weight parts of crystalline copper sulfate to the heated to 80 0 C for one hour coupling solution, and then cooking. After the addition of 41.5 parts by weight of sodium carbonate, the copper (I) oxide is separated off by filtration - optionally with the addition of activated carbon and kieselguhr. The dye is salted out with sodium chloride and isolated.

Le A 12 344Le A 12 344

009883/ 1803009883/1803

Claims (3)

Patentansprüche:Patent claims: 1.) Azofarbstoff der Formel1.) Azo dye of the formula CH=CHCH = CH SO3H HO3SSO 3 H HO 3 S N=NN = N 2. Verfahren zur Herstellung eines Azofarbstoffe, dadurch gekennzeichnet, daß man den Aminoazofarbstoff der Formel2. Process for the preparation of an azo dyes, thereby characterized in that the aminoazo dye of the formula N=N-A VN=N = N-A VN = CH=CHCH = CH SO3H HO3 SO 3 H HO 3 triazoliert.triazolated. 3. Konzentrierte wäßrige Färbstofflusung, enthaltend3. Concentrated aqueous dye liquor containing mindestens 20 % des Farbstoffs des Anspruchs 1.at least 20 % of the dye of claim 1. Le A 12Le A 12 Ö09883/1803Ö09883 / 1803
DE19691932826 1969-06-28 1969-06-28 Azo dye and process for its preparation Pending DE1932826A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
DE19691932826 DE1932826A1 (en) 1969-06-28 1969-06-28 Azo dye and process for its preparation
CH926770A CH501706A (en) 1969-06-28 1970-06-18 Process for the preparation of an azo dye
NL7009298A NL7009298A (en) 1969-06-28 1970-06-24
BR21998170A BR7019981D0 (en) 1969-06-28 1970-06-25 PROCESS FOR THE PREPARATION OF AZOIC DYE AND DYE SOLUTION BASED ON THIS
BE752517D BE752517A (en) 1969-06-28 1970-06-25 AZOIC COLORANT AND PROCESS FOR OBTAINING IT
FR7023758A FR2048017A7 (en) 1969-06-28 1970-06-26
GB1251319D GB1251319A (en) 1969-06-28 1970-06-26

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19691932826 DE1932826A1 (en) 1969-06-28 1969-06-28 Azo dye and process for its preparation

Publications (1)

Publication Number Publication Date
DE1932826A1 true DE1932826A1 (en) 1971-01-14

Family

ID=5738239

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19691932826 Pending DE1932826A1 (en) 1969-06-28 1969-06-28 Azo dye and process for its preparation

Country Status (7)

Country Link
BE (1) BE752517A (en)
BR (1) BR7019981D0 (en)
CH (1) CH501706A (en)
DE (1) DE1932826A1 (en)
FR (1) FR2048017A7 (en)
GB (1) GB1251319A (en)
NL (1) NL7009298A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002081580A1 (en) * 2001-04-04 2002-10-17 Nippon Kayaku Kabushiki Kaisha Aqueous ink composition, water-soluble dye composition and ink-jet recording method
EP1669413A1 (en) * 2003-10-01 2006-06-14 Nippon Kayaku Kabushiki Kaisha Azo compound, aqueous dye solutions containing the same, inks and use thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006096995A (en) * 2004-08-31 2006-04-13 Canon Inc Ink-jet ink, method for making the same, ink-jet printing method, and ink cartridge using the ink

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002081580A1 (en) * 2001-04-04 2002-10-17 Nippon Kayaku Kabushiki Kaisha Aqueous ink composition, water-soluble dye composition and ink-jet recording method
EP1669413A1 (en) * 2003-10-01 2006-06-14 Nippon Kayaku Kabushiki Kaisha Azo compound, aqueous dye solutions containing the same, inks and use thereof
EP1669413A4 (en) * 2003-10-01 2007-12-26 Nippon Kayaku Kk Azo compound, aqueous dye solutions containing the same, inks and use thereof
US7387668B2 (en) 2003-10-01 2008-06-17 Nippon Kayaku Kabushiki Kaisha Azo compound, aqueous dye solutions containing the same, inks and use thereof
JP5237530B2 (en) * 2003-10-01 2013-07-17 日本化薬株式会社 Azo compound, aqueous dye solution, ink and use thereof

Also Published As

Publication number Publication date
CH501706A (en) 1971-01-15
BE752517A (en) 1970-12-01
NL7009298A (en) 1970-12-30
FR2048017A7 (en) 1971-03-19
GB1251319A (en) 1971-10-27
BR7019981D0 (en) 1973-04-19

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