# US 4,392,998 A · One pot diazotization, coupling and quaternization of aminotriazoles

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- Number: US 4,392,998 A
- Document ID: US4392998A
- Status: Granted
- Kind: A
- Application number: 06/236,490
- Filed: 1981-02-23
- Granted: 1983-07-12
- Earliest claimed: 1980-03-11
- Assignees: Bayer Aktiengesellschaft
- Inventors: Hans-Peter Kuhlthau
- Web page: https://patentgrep.com/patent/US4392998A

## CPC

- C09B 44/18: having three nitrogen atoms as the only ring hetero atoms
- D06P 1/08: cationic azo dyes
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- D06P: DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM

## Abstract

In the preparation of a quaternized dyestuff of the formula ##STR1## in which R.sup.1 and R.sup.2 each is an optionally substituted alkyl, alkenyl or aralkyl radical, R.sup.3 is hydrogen, or an optionally substituted alkyl, aralkyl, cycloalkyl or aryl radical, K is the radical of a coupling component+HK, and X is an anion, wherein an aminotriazole of the formula ##STR2## is diazotized and coupled to a coupling component HK to form an intermediate dyestuff of the formula ##STR3## and the intermediate dyestuff is quaternized with an alkylating or aralkylating agent capable of providing the radicals R.sup.1 and R.sup.2 in a medium also providing the anion X.sup.-, the improvement which comprises effecting the coupling at a pH of 4 to 6 and thereafter, without isolation of the intermediate dyestuff, effecting the quaternization.

## Claims

### Claim 1

In the preparation of a quaternized dyestuff of the formula ##STR23## in which R.sup.1 and R.sup.2 each is a C.sub.1 - to C.sub.4 -alkyl or alkenyl radical, or a C.sub.1 -C.sub.4 -alkyl or alkenyl radical substituted by halogen, hydroxyl, cyano, C.sub.1 - to C.sub.4 -alkoxy, C.sub.1 - to C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.3 -alkylcarbonyloxy, aminocarbonyl, phenoxy, benzyloxy, benzoyloxy, mono- or di-(C.sub.1 to C.sub.2 -alkyl)-amino, mono- or di-(C.sub.1 - to C.sub.2 -alkyl)-aminocarbonyl, phenylalkyloxy, phenoxycarbonyloxy or phenylaminocarbonyloxy; a benzyl, .alpha.- or .beta.-phenethyl or .alpha.-, .beta.- or .gamma.-phenylpropyl radical; or a benzyl, .alpha.- or .beta.-phenylethyl or .alpha.-, .beta.- or .gamma.-phenylpropyl radical substituted by C.sub.1 - to C.sub.4 -alkyl or by any of the substituents set forth in connection with alkyl;
R.sub.3 is hydrogen; a C.sub.1 - to C.sub.4 -alkyl radical; a C.sub.1 - to C.sub.4 -alkyl radical substituted as in R.sup.1 and R.sup.2 ; a cyclohexyl, phenyl, naphthyl, benzyl, .alpha.- or .beta.-phenylethyl or .alpha.-, .beta.- or .gamma.-phenylpropyl radical; or a cyclohexyl, phenyl, naphthyl, benzyl, .alpha.- or .beta.-phenylethyl or .alpha.-, .beta.- or .gamma.-phenylpropyl radical substituted by C.sub.1 to C.sub.4 -alkyl or by any of the substituents set forth in connection with alkyl;
K is the radical of a coupling component HK, and p1 X is an anion,
wherein an aminotriazole of the formula ##STR24## is diazotized and coupled to a coupling component HK to form an intermediate dyestuff of the formula ##STR25## and the intermediate dyestuff is quaternized with an alkylating or aralkylating agent capable of providing the radicals R.sup.1 and R.sup.2 in a medium also providing the anion X.sup.-, the improvement which comprises effecting the coupling at a pH of 4 to 6 and thereafter, without isolation of the intermediate dyestuff, effecting the quaternization.

### Claim 2 (depends on 1)

A process according to claim 1, wherein the pH is established by at least one of hydrochloric, sulphuric, formic, propionic and acetic acids.

### Claim 3 (depends on 1)

A process according to claim 1, wherein at least one of water and a water-miscible organic solvent is employed as a solvent.

### Claim 4 (depends on 1)

A process according to claim 1, wherein a water-insoluble organic solvent or an aqueous suspension thereof is employed as a solvent.

### Claim 5 (depends on 1)

A process according to claim 1, wherein the coupling component is an indole of the formula ##STR26##

### Claim 6 (depends on 1)

A process according to claim 1, wherein the coupling component is a compound of the formula ##STR27##