GB243758A - Manufacture of azo-dyestuffs and process of dyeing wool, therewith - Google Patents

Manufacture of azo-dyestuffs and process of dyeing wool, therewith

Info

Publication number
GB243758A
GB243758A GB30024/25A GB3002425A GB243758A GB 243758 A GB243758 A GB 243758A GB 30024/25 A GB30024/25 A GB 30024/25A GB 3002425 A GB3002425 A GB 3002425A GB 243758 A GB243758 A GB 243758A
Authority
GB
United Kingdom
Prior art keywords
sulphophenyl
acid
pyrazolone
carboxylic
methyl
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
GB30024/25A
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.)
Hoechst AG
Original Assignee
Hoechst 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 Hoechst AG filed Critical Hoechst AG
Publication of GB243758A publication Critical patent/GB243758A/en
Expired 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
    • 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
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone

Landscapes

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

Abstract

1-Sulphoaryl - 5-pyrazolone - 3-carboxylic alkyl esters are obtained from the hydrazones from sulphoarylhydrazine sulphonic acids and oxaloacetic esters either by heating in aqueous solution, or by allowing to stand in cold aqueous solution made slightly alkaline with sodium carbonate. The benzene solution of the sodium salt of oxaloacetic ester as obtained in its manufacture may be directly used, the paste of the hydrazine sulphonic acid being added directly thereto, and the benzene subsequently distilled off. Examples are given of the production of 1-(41-sulphophenyl)-5-pyrazolone-3-carboxylic acid ethyl and methyl esters, and 1-(21-methyl-61-chloro-41-sulphophenyl) - 5-pyrazolone-3-carboxylic acid ethyl ester. The 2-methyl-6-chlor-4-sulphophenylhydrazine used in preparing the last-named body is obtained by sulphonating 3-chlor-2-aminotoluene and converting the product into the hydrazine by the usual method. Azo dyes are obtained by coupling the above-described pyrazolones with diazo compounds or by esterifying the dyestuffs from diazo compounds and 1-sulphoaryl-5-pyrazolone-3-carboxylic acids. The products dye wool in level yellow to red shades which may be developed by after-chroming when the dyestuff is derived from the diazo compound of an anthranilic acid or an o-aminophenol. The following amines are mentioned as diazo components:- o-, m-, or p-toluidine, m- or p-chloraniline, chlortoluidines, xylidines, o-, m-, or p-aminobenzoic methyl or ethyl ester, nitroaminobenzoic ester, m-aminobenzoic anilide, m-aminoanisic anilide, o-aminophenol and its substitution products; aniline sulphonic acids and their homologues and substitution products such as o-aniline sulphonic acid, metanilic acid, chlor- and nitroaniline sulphonic acids, toluidine and xylidine sulphonic acids; mono- and di-aminotriphenylmethane, diaminodiphenyldimethylmethane, di-amino-di-o-tolyldimethylmethane, 2 : 21-toluidine, 2 : 21-dichlorbenzidine, diaminodiphenylamine. Examples are given of the production of dyestuffs from (1) m-aminobenzaldehyde, o-chloraniline, sulphanilic acid, 5-nitro-2-aminobenzoic acid, or picramic acid and 1-(41-sulphophenyl)-5- pyrazolone-3-carboxylic ethyl ester; (2) aniline, or 6-chloraniline-3-sulphonic acid, and 1-(21-methyl-61-chloro-41-sulphophenyl) -5-pyrazolone-3-carboxylic ethyl ester. The 1-(21 : 51-dichloro-41-sulphophenyl)-, 1-(21-chloro-51-sulphophenyl)-, 1-(21-sulphophenyl)-, and the 1-(21-oxy-31-carboxy-51-sulphophenyl) -5-pyrazolone-3-carboxylic esters are also mentioned as coupling components. Reference has been directed by the Comptroller to Specifications 765/97 and 3373/08.ALSO:Wool is dyed in level yellow to red shades by means of dyestuffs containing a carboxylic ester group, obtained by coupling diazo compounds with a 1-sulphoaryl-5-pyrazolone-3-carboxylic alkyl ester, or by esterifying the dyestuffs from diazo compounds and the corresponding pyrazolone sulphocarboxylic acids. The following amines are mentioned as diazo components:-o-, m-, or p-toluidine, m- or p-chloraniline, chlortoluidines, xylidines, o-, m-, or p-aminobenzoic methyl or ethyl ester, nitroaminobenzoic ester, m-aminobenzoic anilide, m-aminoanisic anilide, o-aminophenol and its substitution products; aniline sulphonic acids and their homologues and substitution products, such as o-aniline sulphonic acid, metanilic acid, chlor- and nitro-aniline sulphonic acids, toluidine and xylidine sulphonic acids; mono- and di-aminotriphenylmethane, diaminodiphenyldimethylmethane, diaminodi-o-tolyldimethylmethane, 2 : 21-tolidine, 2 : 21-dichlorbenzidine, and diaminodiphenylamine. Examples are given of dyestuffs from (1) m-aminobenzaldehyde, o-chloraniline, sulphanilic acid, 5-nitro-2-aminobenzoic acid or picramic acid and 1-(41-sulphophenyl) - 5pyrazolone - 3 - carboxylic ethyl ester; and (2) aniline or 6-chloraniline-3-sulphonic acid and 1-(21-methyl-61-chlor-41-sulphophenyl) -5-pyrazolone-3-carboxylic ethyl ester. The 1-(21 : 51-dichlor-41-sulphophenyl)-, 1-(21-chlor-51-sulphophenyl)-, 1-(21-sulphophenyl)-, and the 1-(21-oxy-31-carboxy-51-sulphophenyl) -5-pyrazolone - 3 - carboxylic esters are also mentioned as coupling components. Reference has been directed by the Comptroller to Specifications 765/97 and 3373/08, [both in Class 2, Acids and salts, Organic &c.].
GB30024/25A 1924-11-27 1925-11-27 Manufacture of azo-dyestuffs and process of dyeing wool, therewith Expired GB243758A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE243758X 1924-11-27

Publications (1)

Publication Number Publication Date
GB243758A true GB243758A (en) 1927-02-24

Family

ID=5922432

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30024/25A Expired GB243758A (en) 1924-11-27 1925-11-27 Manufacture of azo-dyestuffs and process of dyeing wool, therewith

Country Status (1)

Country Link
GB (1) GB243758A (en)

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