CS216607B1 - Chromcomplex azodyes containing the remainder of the citrazine acid in the molecule and method of preparation of the same - Google Patents

Chromcomplex azodyes containing the remainder of the citrazine acid in the molecule and method of preparation of the same Download PDF

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Publication number
CS216607B1
CS216607B1 CS78632A CS63278A CS216607B1 CS 216607 B1 CS216607 B1 CS 216607B1 CS 78632 A CS78632 A CS 78632A CS 63278 A CS63278 A CS 63278A CS 216607 B1 CS216607 B1 CS 216607B1
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CS
Czechoslovakia
Prior art keywords
carbon atoms
alkyl contains
molecule
preparation
chromcomplex
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CS78632A
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Czech (cs)
Inventor
Ales Cee
Jan Dvorak
Vladimir Chmatal
Petr Kuthan
Josef Vencl
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Ales Cee
Jan Dvorak
Vladimir Chmatal
Petr Kuthan
Josef Vencl
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Application filed by Ales Cee, Jan Dvorak, Vladimir Chmatal, Petr Kuthan, Josef Vencl filed Critical Ales Cee
Priority to CS78632A priority Critical patent/CS216607B1/en
Publication of CS216607B1 publication Critical patent/CS216607B1/en

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    • 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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
    • C09B62/006—Azodyes
    • C09B62/008—Monoazo dyes
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
    • C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings

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

The process serves to prepare novel, citrazinoyl-containing azo dyes of the formula I <IMAGE> where Ar, R, R1, R2 and R3 are each as defined in Claim 1. Said azo dyes are prepared by coupling diazotised aromatic amines of the general formula II <IMAGE> with compounds of the general formula III <IMAGE>

Description

Vynález se týká cUгlP)oomplee□lícU azobarviv obalujících jako pasivní komipmentu zbytek kyseliny citrazinové a způsobu jejich přípravy.BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to clogs of azo dyes coated as a passive composite with a residue of citrazic acid and a process for their preparation.

Kovokomppemí barviva obsan^jcí heterocyklické sloučeniny a zbytek kyseliny citrazinové v pooekiu.e jsou známá z US pat. 2,857.372. Rovněž jsou' známa barviva obsaiující kyselinu citrazinovou, která mjjí charakter barviv přímých disperzních a reaktivních.The metal-composite dyes containing the heterocyclic compound and the residue of citrazic acid in the polymer are known from US Pat. 2,857.372. Dyes containing citrazic acid are also known which have the character of direct dispersive and reactive dyes.

Nyní bylo zjištěno, že lze tato barviva doplet o cUrlPoommPe:иní sloučeniny obsahující sloučeniny benzenové řady s hyйrlxys0upinlU v o-poloze k azoskupině.It has now been found that these dyes can be confused with the CrPoommPe: compounds containing benzene series compounds with hydroxyl groups in the o-position to the azo group.

Způsobpřípravy cUrlmkoppPlэαlícU azobarviv vzorce · I,Method for the preparation of the azo dyes of the formula I,

216 607216 607

216 607216 607

kde značíwhere it indicates

R hydroxyl, alkoxyl, kde alkyl obsahuje 1 až 12 atomů uhlíku, aminoskuplnu, dialkylaminoskupinu, kde alkyl obsahuje 1-16 atomů uhlíku, alkylaminoskuplnu, kde alkyl obsahuje 1-16 atomů uhlíku,R is hydroxyl, alkoxy wherein the alkyl contains 1 to 12 carbon atoms, the amino group, a dialkylamino group wherein the alkyl contains 1-16 carbon atoms, the alkylamino group wherein the alkyl contains 1-16 carbon atoms,

R^ vodík, halogen, sulfo-, nitroskupinu,R ^ is hydrogen, halogen, sulfo-, nitro,

R2 hydroskupinu v o-poloze к azoskuplně, spočívá podle vynálezu v tom, že diazotovaný aromatický amin vzorce II,The R 2 hydro group in the o-position to the azosubstituted group consists in that the diazotized aromatic amine of formula II

(II) kde R, R^ a R2 mají výše uvedený význam, reaguje s kyselinou citrazinovou nebo jejími deriváty vzorce III,(II) wherein R, R 1 and R 2 are as defined above, react with citrazinic acid or its derivatives of formula III,

(ΠΙ) kde R značí hydroxyskupinu, álkoxyl, kde alkyl obsahuje 1 až 12 atomů uhlíku, ami no skupí nu, dialkylaminoskuplnu, kde alkyl obsahuje 1-12 atomů uhlíku, alkylaminoskupinu, kde alkyl obsahuje 1-12 atomů uhlíku, a na vzniklou sloučeninu se působí chromltými(ΠΙ) where R stands for hydroxy, alkoxy, where alkyl contains 1 to 12 carbon atoms, amino, dialkylamino, where alkyl contains 1-12 carbon atoms, alkylamino, where alkyl contains 1-12 carbon atoms, and for the compound formed is treated with chrome

216 607 solemi v neutrálním až mírně áLkelickém prostředí.216 607 salts in a neutral to slightly alkali environment.

Níže uvedené příklady , uvádějí ilustrativně provedení podle vynálezu.The examples below illustrate embodiments of the invention illustratively.

Příklad 1Example 1

14,3 dílu 4-chlor-2-aminofenolu bylo rozpuštěno při 60 °C v 400 mL vody a . 100 ml 2,5N kyseliny solně. Po oclhLazení zevně ledem na 10 °C b/1 amiinfenol «diazotován přikapáním roztoku 6,9 hmot, dílu dusitanu sodného v 30 tíl vody. Roztok diazoniové soli byl sklerován, rozmíchán s 2 g karto г afinu a po filtraci byl během 30 minut přikapán za míchání do roztoku 15,5 hmot, dílu kyseliny citrazinové, rozpuštěné ve 200 ml vody, a 120 m 2,5N roztoku uiličitanu sodného. Pasta barviva byla rozmíchána v 1000 m. vody, 100 mi 36% hydroxidu amonného a 31 hmot, dílů kyseliny chromsaaicylové (obsahuje 12 % hmot, chrómu). Reakční směs udržována ve varu celkem 12 hodin, až v průběhu reakce vznikaaící chromcornple^rní barvivo (poměr barvivo : chrom 1 : 1) přejde na komplex 2 : 1. Po skončení reakce byl roztok vysrážen kyselinou solnou, zfiirrován a filtrační koláč promet 10% solankou. Po vysušení bylo získáno 36 hmrt, dílů barviva, které po vybarvení na animéáních vláknech poskytuje sytě červenohnědé odstíny s dobrými mkrýmí stálostmi a dobrou světlost&ostí.14.3 parts of 4-chloro-2-aminophenol were dissolved at 60 ° C in 400 mL of water and. 100 ml of 2,5N hydrochloric acid. After oclhLazení externally of ice at 10 ° C b / 1 amiinfenol «diazotized by dropwise addition of a solution of 6.9 wt. Parts of sodium nitrite in 30 TIL water. The diazonium salt solution was sclerated, stirred with 2 g of carto afine and after filtration dropwise over 30 minutes into a solution of 15.5 parts by weight of citrazic acid dissolved in 200 ml of water and 120 ml of 2.5 N sodium nitrate solution. The dye paste was mixed in 1000 m. Of water, 100 ml. Of 36% ammonium hydroxide and 31 wt. Parts of chromsaaicylic acid (containing 12 wt.%, Chromium). The reaction mixture was kept under boiling for a total of 12 hours until the chromocapple dye (dye: chromium ratio 1: 1) formed during the reaction turned to a 2: 1 complex. After completion of the reaction, the solution was precipitated with hydrochloric acid, filtered and filtered. brine. After drying, 36 parts by weight of dye were obtained which, after dyeing on the animated fibers, gave deep reddish-brown shades with good wet fastness and good brightness.

Příklad 2 .Example 2.

Analogickým způsobem jako u příkladu 1 byl připraven chromitý komppex barviva z 15,4 hmot, dílů 4-nitro-2-aminofenolu.In a manner analogous to Example 1, a chromium dye complex was prepared from 15.4 parts by weight of 4-nitro-2-aminophenol.

Re akční dobu chromace bylo možno upravit na 6 hodin. Isolované barvivo vybarvuje vlákna tmavo červeným odstínem.The reaction time of the chromation could be adjusted to 6 hours. The isolated dye colors the fibers with a dark red hue.

Nová barviva barví animéání vlákno červenohnědým odstínem.The new dyes stain the animating fiber with a reddish brown tint.

Claims (2)

1· Chrankomplexní azobarviva obsahující zbytek kyseliny citrazinové v molekule obecného (I) kde značí1 Complex azo dyes containing the citrazinic acid residue in the molecule of general formula (I) where it denotes R hydroxyl, alkoxyl, kde alkyl obsahuje 1 až 12 atomů uhlíku, aminoskupinu, dialkylaminoskupinu, kde alkyl obsahuje 1 až 16 atomů uhlíku, alkylaminoskupinu, kde alkyl obsahuje 1 až 16 atomů uhlíkuR is hydroxyl, alkoxy, wherein alkyl contains 1 to 12 carbon atoms, amino, dialkylamino, wherein alkyl contains 1 to 16 carbon atoms, alkylamino, wherein alkyl contains 1 to 16 carbon atoms R^ vodík, halogen, sulfo-, nitroskupinuR @ 1 is hydrogen, halogen, sulfo-, nitro R2 hydroxyskupinu v o-poloze к azoskupině.R 2 hydroxy group in the o-position to the azo link к. 2. Způsob přípravy barviv podle bodu 1, vyznačený tím, Že diezotovaný aromatický amin vzorce II, kde značí2. A process according to claim 1, wherein the deprotected aromatic amine of formula II, wherein R^ vodík, halogen, sulfo- nitroskupinu,R 2 is hydrogen, halogen, sulfonitro, R2 hydroxyskupinu v o-poloze к azoskupině, reaguje s kyselinou citrazinovou nebo jejími deriváty vzorce III,R 2 hydroxy group in the o-position к azo group, is reacted with citrazinic acid or its derivatives of formula III 216 607 (Ш) kde R značí hydroxyskupinu, alkoxyl, kde alkyl obsahuje 1 až 12 atomů uhlíku, aminoskupinu, dialkylaminoskupinu, kde alkyl obsahuje 1-12, alkylaminoskupinu, kde alkyl obsahuje 1 až 12 atomů uhlíku, a na vzniklou sloučeninu se působí chromitýml solemi v neutrálním až mírně alkalickém prostředí.216,607 (Ш) wherein R is hydroxy, alkoxy, wherein the alkyl contains 1 to 12 carbon atoms, amino, dialkylamino, wherein the alkyl contains 1-12, alkylamino, wherein the alkyl contains 1 to 12 carbon atoms, and the resulting compound is treated with chromium salts in a neutral to slightly alkaline environment.
CS78632A 1976-12-15 1978-01-31 Chromcomplex azodyes containing the remainder of the citrazine acid in the molecule and method of preparation of the same CS216607B1 (en)

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CS819276A CS216606B1 (en) 1976-12-15 1976-12-15 Azodyes containing the remainder of the citrazine acid in the molecule and method of preparation the same
CS78632A CS216607B1 (en) 1976-12-15 1978-01-31 Chromcomplex azodyes containing the remainder of the citrazine acid in the molecule and method of preparation of the same

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ300680B6 (en) * 2007-09-25 2009-07-15 Univerzita Pardubice Metal complex azo dyes based on citrazinic acid, process of their preparation and method of dyeing animal and synthetic substrates

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ300680B6 (en) * 2007-09-25 2009-07-15 Univerzita Pardubice Metal complex azo dyes based on citrazinic acid, process of their preparation and method of dyeing animal and synthetic substrates

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CH634092A5 (en) 1983-01-14
DE2755683A1 (en) 1978-06-22
CS216606B1 (en) 1982-11-26

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