DE455278C - Process for the preparation of triarylmethane dyes - Google Patents

Process for the preparation of triarylmethane dyes

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Publication number
DE455278C
DE455278C DEI27646D DEI0027646D DE455278C DE 455278 C DE455278 C DE 455278C DE I27646 D DEI27646 D DE I27646D DE I0027646 D DEI0027646 D DE I0027646D DE 455278 C DE455278 C DE 455278C
Authority
DE
Germany
Prior art keywords
triarylmethane dyes
preparation
acid
weight
oxy
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
DEI27646D
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German (de)
Inventor
Dr Hermann Stoetter
Dr Berthold Wenk
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 DEI27646D priority Critical patent/DE455278C/en
Application granted granted Critical
Publication of DE455278C publication Critical patent/DE455278C/en
Expired legal-status Critical Current

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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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Darstellung von Triarylmethanfarbstoffen. Es ist bekannt, daß man durch Kondensation von Oxydiarylmethanen mit aromatischen Oxykörpern mit Nitrosylschwefelsäure in starker Schwefelsäure Triarylmethanfarbstoffe erhält.Process for the preparation of triarylmethane dyes. It is known, that by condensation of oxydiarylmethanes with aromatic oxy bodies with Nitrosylsulfuric acid in strong sulfuric acid gives triarylmethane dyes.

Es, wurde nun die bemerkenswerte Beobachtung gemacht, daß man zu wertvollen Triarylmethanfarbstoffen in viel einfacherer Weise dadurch gelangen kann daß man Oxydiarylmethane oder Oxydiarylhydrole oder allgemein paramethylierte aromatische Oxykörper gemeinsam mit aromatischen Oxyverbindungen in alkalischer Lösung oxydiert.It has now been made the remarkable observation that one is too valuable Triarylmethane dyes can be obtained in a much simpler manner in that one Oxydiarylmethanes or oxydiarylhydrols or, in general, paramethylated aromatic Oxy bodies are oxidized together with aromatic oxy compounds in an alkaline solution.

Beispiel i.Example i.

31,6 Gewichtsteile Methylen-di-o-kresotinsäure und 3q.,$ Gewichtsteile 2-oxvnaphthalin-3 # 6-disulfosaures Natrium werden z. B. mit .a.75 Gewichtsteilen 17prozentiger Natronlauge gelöst und zur besseren Sauerstoffübertragung unter Zusatz von i Gewichtsteil Kupfervitriol oder irgendeines anderen Sauerstoffüberträgers bei 9o° intensiv mit Luft verrührt. Es wird so lange gerührt, bis keine Farbstoffzunahme mehr erfolgt. Der entstandene Farbstoff wird in üblicher Weise isoliert und gibt auf Wolle, nachchromiert, ein rötliches Blau. Beispiel e.31.6 parts by weight of methylene-di-o-cresotinic acid and 3q. $ Parts by weight 2-oxnaphthalene-3 # 6-disulfonic acid sodium are z. B. with .a.75 parts by weight 17 percent sodium hydroxide solution dissolved and for better oxygen transfer with additive of 1 part by weight of vitriol or any other oxygen carrier stirred intensively with air at 90 °. It is stirred until there is no increase in dye more is done. The resulting dye is isolated in the usual way and gives on wool, chromed, a reddish blue. Example e.

15,2 Gewichtsteile p-Kresotinsäure und 30,4 Gewichtsteile o-Kresotinsäure werden mit 475 Gewichtsteilen i 7prozentiger Natronlauge gelöst und wie in Beispiel i oxydiert. Der entstandene Farbstoff gibt auf Wolle, nachchromiert, ein rotstichiges Violett.15.2 parts by weight of p-cresotinic acid and 30.4 parts by weight of o-cresotinic acid are dissolved with 475 parts by weight of i 7 percent sodium hydroxide solution and as in example i oxidized. The resulting dye gives a reddish tinge to wool after it has been chromed Violet.

An Stelle von Methylen-di-o-kresotinsäure in Beispiel i kann man andere Oxydiarylmethane nehmen, wie z. B. Methylen-di-okresol, Methylen-di-salicylsäure, Oxydiphenylmethan und seine Abkömmlinge oder auch unsymmetrische Methane, wie z. B.4'-Diäthylamino- 3 -methyl-4-,Oxy-5-carboxydiphenylmethan oder 4'- Oxy - 3'- carboxynaphthyl-3-methyl-4-oxy-5-carboxyphenylmethan oder die den Methanen entsprechende Hydrole.Instead of methylene-di-o-cresotinic acid in Example i, others can be used Take oxydiarylmethanes, such as. B. methylene-di-okresol, methylene-di-salicylic acid, Oxydiphenylmethane and its derivatives or asymmetrical methanes, such as. B. 4'-diethylamino-3-methyl-4-, oxy-5-carboxydiphenylmethane or 4'-oxy-3'-carboxynaphthyl-3-methyl-4-oxy-5-carboxyphenylmethane or the hydrols corresponding to the methanes.

An Stelle von 2-naphthol-3 # 6-disulfosauires Natrium in Beispiel i kann man 2-Naphthol und seine Abkömmlinge (wie Sulfo- und Carbonsäuren), ebenso entsprechende Abkömmlinge des i-Naphthols und Polyoxynaphthaline, Phenole, Polyoxybenzole oder ihre Sulfo- und Carbonsäuren nehmen.Instead of 2-naphthol-3 # 6-disulfosauires sodium in example i can get 2-naphthol and its derivatives (such as sulfo and carboxylic acids), as well corresponding derivatives of i-naphthol and polyoxynaphthalenes, phenols, polyoxybenzenes or take their sulfo and carboxylic acids.

In Beispiel 2 kann an Stelle der p-Kresotinsäure genommen werden p-Kresol und seine Abkömmlinge. An Stelle der o-Kresotinsäure in Beispiel 2 können andere aromatische Oxysäuren oder auch Phenol, Kresole oder deren Substitutionsprodukte oder auch Gemische, z. B. o-Kresotinsäure + 2-Oxy-3-naphthoesäure, genommen werden.In Example 2, p-cresol can be used in place of p-cresotinic acid and its descendants. Instead of o-cresotinic acid in example 2 can be other aromatic oxyacids or phenol, cresols or their substitution products or mixtures, e.g. B. o-cresotinic acid + 2-oxy-3-naphthoic acid can be taken.

.An Stelle von Luftsauerstoff können auch andere Oxydationsmittel, wie z. B. Braunstein oder Bleisuperoxyd, Verwendung finden.Instead of atmospheric oxygen, other oxidizing agents, such as B. Brownstone or lead peroxide, find use.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Triarylmethanfarbstoffen, darin bestehend, daB man Oxydiarylinethane oder Oxydiarylhydrole oder allgemein paramethylierte aromatische Oxykörper gemeinsam mit aromatischen Oxyverbindungen in alkalischer Lösung oxydiert.PATENT CLAIM: Process for the preparation of triarylmethane dyes, consisting in using oxydiarylinethanes or oxydiarylhydrols or in general paramethylated aromatic oxy bodies together with aromatic oxy compounds oxidized in alkaline solution.
DEI27646D 1926-03-13 1926-03-13 Process for the preparation of triarylmethane dyes Expired DE455278C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI27646D DE455278C (en) 1926-03-13 1926-03-13 Process for the preparation of triarylmethane dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI27646D DE455278C (en) 1926-03-13 1926-03-13 Process for the preparation of triarylmethane dyes

Publications (1)

Publication Number Publication Date
DE455278C true DE455278C (en) 1928-01-28

Family

ID=7186822

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI27646D Expired DE455278C (en) 1926-03-13 1926-03-13 Process for the preparation of triarylmethane dyes

Country Status (1)

Country Link
DE (1) DE455278C (en)

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