GB868594A - New mono-and dis-azo dyestuffs containing halogenoacylamino groups - Google Patents

New mono-and dis-azo dyestuffs containing halogenoacylamino groups

Info

Publication number
GB868594A
GB868594A GB2000458A GB2000458A GB868594A GB 868594 A GB868594 A GB 868594A GB 2000458 A GB2000458 A GB 2000458A GB 2000458 A GB2000458 A GB 2000458A GB 868594 A GB868594 A GB 868594A
Authority
GB
United Kingdom
Prior art keywords
methyl
sulphon
aminobenzene
chloroacetylaminophenyl
pyrazolone
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
GB2000458A
Inventor
Alexander Blackhall
Robert Ronald Davies
Cyril Eric Vellins
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB2000458A priority Critical patent/GB868594A/en
Publication of GB868594A publication Critical patent/GB868594A/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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/465—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an acryloyl group, a quaternised or non-quaternised aminoalkyl carbonyl group or a (—N)n—CO—A—O—X or (—N)n—CO—A—Hal group, wherein A is an alkylene or alkylidene group, X is hydrogen or an acyl radical of an organic or inorganic acid, Hal is a halogen atom, and n is 0 or 1
    • C09B62/47—Azo dyes

Abstract

The invention comprises azo dyestuffs of formula:- <FORM:0868594/IV(c)/1> wherein A is the residue of a mono- or dis-azo compound free from sulphonic or carboxylic acid groups, n and m are 1 or 2, X is -NH- or -NR- wherein R is an alkyl radical, Y is a halogenoalkyl radical, Z is -NH2, -NHR1, -NR1 R11, -NHSO2R11, -NHCOR1 or alkyl, wherein R1 and R11 are substituted or unsubstituted hydrocarbon radicals, and the dyestuffs contain not more than one hydroxy group in ortho position to each azo group. The dyes may be made by normal diazotization and coupling procedures using suitable components and many components are specified. Alternatively they may be prepared by reacting an aminoazo compound of formula:- <FORM:0868594/IV(c)/2> with an acylating agent B.CO.Y wherein B is a halogen atom. The dyes give yellow, orange and red shades on wool, silk and synthetic polyamides. In examples: (1) the dyes 4-amino-benzene-sulphonamide--> 1-chloroacetylamino-7-naphthol, or 1-(21-methyl-51-chloroacetylaminophenyl) - 3-methyl- 5-pyrazolone, 2-aminophenyl methyl sulphone or 1- aminobenzene- 3-sulphon-N-acetylamide or 1-aminobenzene- 3-sulphon-N-benzoylamide or 1-aminobenzene-3-sulphon-N-methane sulphonamide or 1-aminobenzene-3-sulphon-N-p-toluene sulphonamide --> 1-(21-methyl- 51-chloroacetylaminophenyl) - 3-methyl-5-pyrazolone, 1-aminobenzene- 3-sulphon-N-p-toluene sulphonamide --> 4-acetoacetylaminoo -chloroacetanilide, 4-methyl- 3-(N-ethyl- N-chloroacetyl) aminoaniline --> 2-naphthol- 6-sulphonamide, bis (1-aminobenzene- 3-sulphon) imide (1 mol) \sQ 1-(21-methyl- 51-chloroacetylaminophenyl) - 3-methyl- 5-pyrazolone (2 mols) and 3 : 31- dimethoxy-4 : 41-diamino-6 : 61-di (N : N-diethylsulphamyl) diphenyl (1 mol) \sQ 1-(31-chloroacetylaminophenyl)- 3-methyl- 5-pyrazolone (2 mols) are prepared; (2) the dye m- or p-aminoacetanilide --> 1-[31-sulphon- N-(p-toluenesulphonyl) amidophenyl]- 3-methyl- 5- pyr-. azolone is hydrolysed with hydrochloric acid and the aminoazo dye reacted with chloroacetyl chloride; (3) the dye 1-aminobenzene- 3-sulphon-N- p-toluene sulphonamide --> cresidine is reacted with chloroacetylchloride; (4) the dye 1-(2-methyl- 5-chloroacetylaminophenyl)- 3-methyl -4-(411-sulphonamidophenylazo)- 5-pyrazolone is reacted with chloroacetyl chloride to give 1-(21-methyl- 51-chloroacetylaminophenyl) - 3-methyl-4-[411-(sulphon- N-chloroacetylamido) phenylazo]- 5-pyrazolone.
GB2000458A 1958-06-23 1958-06-23 New mono-and dis-azo dyestuffs containing halogenoacylamino groups Expired GB868594A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2000458A GB868594A (en) 1958-06-23 1958-06-23 New mono-and dis-azo dyestuffs containing halogenoacylamino groups

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2000458A GB868594A (en) 1958-06-23 1958-06-23 New mono-and dis-azo dyestuffs containing halogenoacylamino groups

Publications (1)

Publication Number Publication Date
GB868594A true GB868594A (en) 1961-05-17

Family

ID=10138751

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2000458A Expired GB868594A (en) 1958-06-23 1958-06-23 New mono-and dis-azo dyestuffs containing halogenoacylamino groups

Country Status (1)

Country Link
GB (1) GB868594A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5696242A (en) * 1994-08-04 1997-12-09 Clariant Finance (Bvi) Limited Polyazo dyes containing the radical of a bis-coupling component, and process for their production

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5696242A (en) * 1994-08-04 1997-12-09 Clariant Finance (Bvi) Limited Polyazo dyes containing the radical of a bis-coupling component, and process for their production

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