GB2030163A - Benzisothiazole-azo dyes - Google Patents

Benzisothiazole-azo dyes Download PDF

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Publication number
GB2030163A
GB2030163A GB7925014A GB7925014A GB2030163A GB 2030163 A GB2030163 A GB 2030163A GB 7925014 A GB7925014 A GB 7925014A GB 7925014 A GB7925014 A GB 7925014A GB 2030163 A GB2030163 A GB 2030163A
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GB
United Kingdom
Prior art keywords
dye
parts
formula
benzisothiazole
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.)
Withdrawn
Application number
GB7925014A
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of GB2030163A publication Critical patent/GB2030163A/en
Withdrawn legal-status Critical Current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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0805—Amino benzenes free of acid groups
    • C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
    • C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
    • C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
    • C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
    • 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
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
    • C09B29/0081—Isothiazoles or condensed isothiazoles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Coloring (AREA)

Abstract

The invention provides novel dyes of the general formula <IMAGE> where R<1> is C1-C4-alkyl, R<2> is methyl, ethyl, propyl or isopropyl and X is hydrogen or methyl. The dyes are mainly used for dyeing synthetic polyester textiles.

Description

SPECIFICATION Benzisothiazole-azo dyes The present invention relates to benzisothiazole-azo dyes.
According to the invention there are provided dyes of the general formula
where R1 is C1-C4-alkyl, R2 is methyl, ethyl, propyl or isopropyl and Xis hydrogen or methyl.
A compound of the formula I may be prepared by reacting the diazonium compound Sof the amine ofthe formula
with a coupling component of the formula
where R1, R2 and X have the above meanings.
Details of the preferred method of preparafion may be found in the Examples, where parts and percentages are by weight, unless stated otherwise.
On cellulose esters and especially on polyesters, compounds of the formula I give blue dyeings distinguished by good lightfastness, very good wetfastness and adequate fastness to thermofixing. They can also be employed for dyeing with carriers, but are preferably used bythe HT or thermosol process.
In contrast to the commercially available dye of the formula
the compounds according to the invention -exist in one modification only, which can readily be used even for cheese dyeing. Further, dyeings subjected to a subsequent fixing process exhibit improved fastness to wet treatments when compared to dyeings using the commercial product.
Amongst the dyes of the formula I, those where R1 is C3H5 and R2 is CH3 are preferred. Further, X is preferably H.
Example 7 9.8 parts of 3-amino-5-nitro-2,1-benzisothiazole are introduced into -50 parts of 85 percent strength sulfuric acid at 10 - 15"C. 15.5 parts of 45 percent strength nitrosylsulfuric acid are added dropwise to this solution at 0 - BC. The resulting diazonium salt solution isthen stirred for 3 hours at 0 - 5 C, after which a solution of 10.4 parts of N-ethyl-N-acetoxyethylaniline in 10 parts of acetic acid is added dropwise at the same temperature.
Thereafter, the mixture obtained is run, at 0 - 5 C, into 250 parts of water and 250 parts of ice, whilst keeping the pH at 2 by simultaneously introducing sodium acetate solution. After completion of coupling, the mixture is stirred for a further 1 - 2 hours and the dye which has precipitated is filtered off, washed neutral with water and dried under reduced pressure at 50 C. 16.5 parts of the dye oftheformula
are obtained. On polyesters and cellulose esters, this dye gives intense blue dyeings having good fastness characteristics.
Example 2 9.8 parts of 3-amino-5-nitro-2,1 -benzisothiazole are introduced into 50 parts of 85 percent strength sulfuric acid at 10 - 15"C. 15.5 parts of 45 percent strength nitrosyisulfuric acid are added dropwise to this solution at 0 - 5"C. The resuiting diazonium salt solution is stirred for a further 3 hours at O - 5"C and is then run, at the same temperature, into a solution of 11.1 parts of N-ethyl-N--acetoxyethyl-m-toluidine in 10 parts of concentrated hydrochloric acid, 250 parts of water and 250 parts of ice. The pH is then brought to 2 by adding sodium acetate. 16 parts of the dye of the formula
are obtained. On polyesters and cellulose esters, this dye gives intense blue dyeings having good fastness characteristics.
Using methods similar to those described, the dyes identified, in the Examples below, by specifying the substituents are obtained; on polyester fibers, these products give blue dyeings.
Exansple H1 R2 X 3 C2H5 C2115 H c2H C2H5 OH3 5 C2H5 C3H7(n) OH3 6 2 C3H7(n) H 7 or3 CH) H 7 CH3 CH3 H 8 C 4H9 OH3 H OH 9 C2115 C113 OH3 OH3

Claims (6)

1. A benzisothiazole-azo dye of the general formula
where R1 is C-C4-alkyl, R2 is methyl, ethyl, propyl or isopropyl and Xis hydrogen or methyl.
2. A dye as claimed in claim 1 wherein R1 is C2H5 and R2 is CH3.
3. A dye as claimed in claim 1 and identified in any of the foregoing Examples.
4. A process for the preparation of a dye as claimed in claim 1, wherein the diazonium compound of the amine of the formula
is reacted with a coupling component of the formula
where R', R2 and X have the meanings given in claim 1.
5. A process for dyeing cellulose ester and/or polyester textile material wherein a dye as claimed in any of claims 1 to 3 or prepared by a process as claimed in claim 4 is used.
6. A process as claimed in claim 5 carried out according to the HT or thermosol method.
GB7925014A 1978-07-19 1979-07-18 Benzisothiazole-azo dyes Withdrawn GB2030163A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19782831675 DE2831675A1 (en) 1978-07-19 1978-07-19 BENZISOTHIAZOLAZO DYES

Publications (1)

Publication Number Publication Date
GB2030163A true GB2030163A (en) 1980-04-02

Family

ID=6044766

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7925014A Withdrawn GB2030163A (en) 1978-07-19 1979-07-18 Benzisothiazole-azo dyes

Country Status (2)

Country Link
DE (1) DE2831675A1 (en)
GB (1) GB2030163A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0086388A1 (en) * 1982-02-12 1983-08-24 BASF Aktiengesellschaft Dyestuff mixtures
US4464181A (en) * 1982-02-12 1984-08-07 Basf Aktiengesellschaft Mixtures of benzisothiazole mono-azo dyes for cellulose acetate
US5567470A (en) * 1991-07-31 1996-10-22 Mitsui Toatsu Chemicals, Incorporated Heat-sensitive transfer sheet containing blue dyestuff
WO2000043454A1 (en) * 1999-01-22 2000-07-27 Yorkshire Chemicals Plc Dye composition
CN114806212A (en) * 2022-04-11 2022-07-29 乐平市赛复乐医药化工有限公司 Brilliant blue disperse dye compound, mixture, composition, preparation method and application thereof

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0086388A1 (en) * 1982-02-12 1983-08-24 BASF Aktiengesellschaft Dyestuff mixtures
JPS58147460A (en) * 1982-02-12 1983-09-02 バスフ　アクチェン　ゲゼルシャフト Dye mixture
US4464181A (en) * 1982-02-12 1984-08-07 Basf Aktiengesellschaft Mixtures of benzisothiazole mono-azo dyes for cellulose acetate
US5567470A (en) * 1991-07-31 1996-10-22 Mitsui Toatsu Chemicals, Incorporated Heat-sensitive transfer sheet containing blue dyestuff
WO2000043454A1 (en) * 1999-01-22 2000-07-27 Yorkshire Chemicals Plc Dye composition
US6365718B1 (en) 1999-01-22 2002-04-02 Yorkshire Chemicals Plc Dye composition
EP1223199A1 (en) * 1999-01-22 2002-07-17 Yorkshire Chemicals Plc. Dye composition
CN114806212A (en) * 2022-04-11 2022-07-29 乐平市赛复乐医药化工有限公司 Brilliant blue disperse dye compound, mixture, composition, preparation method and application thereof

Also Published As

Publication number Publication date
DE2831675A1 (en) 1980-02-07

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