# US 5,352,774 A · Dyes containing thiophene radicals

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- Number: US 5,352,774 A
- Document ID: US5352774A
- Status: Granted
- Kind: A
- Application number: 08/125,666
- Filed: 1993-09-23
- Granted: 1994-10-04
- Earliest claimed: 1985-05-14
- Assignees: Sandoz Ltd.
- Inventors: Guenter Hansen; Ernst Schefczik; Karl-Heinz Etzbach; Helmut Reichelt; Hermann Loeffler
- Web page: https://patentgrep.com/patent/US5352774A

## CPC

- C09B 29/0059: {the heterocyclic ring containing only sulfur as heteroatom}
- 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)

## Abstract

The compounds of the general formula I ##STR1## where X is fluorine, chlorine, bromine, SO.sub.2 E or unsubstituted or substituted hydroxyl or mercapto, E is alkyl, alkenyl, cycloalkyl, aralkyl, aryl, chlorine or unsubstituted or substituted hydroxyl or amino, Y is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carboxyl, a carboxylic ester group or unsubstituted or substituted carbamyl, T is hydrogen, C.sub.1 -C.sub.4 -alkyl, a radical which can be introduced by electrophilic substitution or a radical of the formula --CH.dbd.B, in which B is a radical of a methylene-active compound or of an amine, and K is a radical of a coupling component, are very useful for dyeing synthetic fibers or plastics.

## Claims

### Claim 1

A compound of the formula: ##STR534## wherein X is fluorine, chlorine or bromine;
Y is cyano;
T is hydrogen; C.sub.1 -C.sub.4 -alkyl; Cl; Br; NO; NO.sub.2 ; SO.sub.3 H; CHO; CN; CH.sub.3 CO; C.sub.2 H.sub.5 CO; C.sub.6 H.sub.5 CO; CH.sub.3 SO.sub.2 ; C.sub.2 H.sub.5 SO.sub.2 ; C.sub.6 H.sub.5 SO.sub.2 ; or --CH.dbd.B;
B is C(CN) (Z) where Z is cyano; nitro; alkanoyl; aroyl; alkylsulfonyl; arylsulfonyl; carboxyl; a carboxylic ester group; unsubstituted carbamyl; substituted carbamyl; or a radical of a compound of one of the formulae: ##STR535## and K is a radical derived from a coupling component of the formula: ##STR536## wherein: B.sup.1 is hydrogen or B.sup.2 ;
B.sup.2 is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkyl substituted by chlorine, bromine, hydroxyl, C.sub.1 -C.sub.8 -alkoxy, phenoxy, phenyl, cyano, carboxyl, C.sub.1 -C.sub.8 -alkanoyloxy, C.sub.1 -C.sub.8 -alkoxy-C.sub.1 -C.sub.4 -alkoxy, benzoyloxy, o-, m- or p-methylbenzoyloxy, o-, m- or p-chlorobenzoyloxy, C.sub.1 -C.sub.8 -alkoxyalkanoyloxy, phenoxyalkanoyloxy, C.sub.1 -C.sub.8 -alkoxycarbonyloxy, C.sub.1 -C.sub.8 -alkoxyalkoxycarbonyloxy, benzyloxycarbonyloxy, phenethoxycarbonyloxy, phenoxyethoxycarbonyloxy, C.sub.1 -C.sub.8 -alkylaminocarbonyloxy, cyclohexylaminocarbonyloxy, phenylaminocarbonyloxy, C.sub.1 -C.sub.8 -alkoxycarbonyl, C.sub.1 -C.sub.8 -alkoxyalkoxycarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenoxy-C.sub.1 -C.sub.4 -alkoxy, phenylethoxycarbonyl, phenyl, or cyclohexyl; and R.sup.6 is cyano; carbamyl; nitro; acetyl; alkoxycarbonyl; methylaminocarbonyl; dimethylaminocarbonyl; ethylaminocarbonyl; diethylaminocarbonyl; methoxyethoxycarbonyl; ethoxyethoxycarbonyl; n-propoxyethoxycarbonyl; isopropoxyethoxycarbonyl; n-butoxyethoxycarbonyl; isobutoxyethoxycarbonyl; or sec.-butoxyethoxycarbonyl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein X is fluorine.

### Claim 3 (depends on 1)

The compound of claim 1, wherein X is chlorine.

### Claim 4 (depends on 1)

The compound of claim 1, wherein X is bromine.

### Claim 5 (depends on 1)

The compound of claim 1, wherein T is hydrogen or C.sub.1-4 alkyl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein T is Cl or Br.

### Claim 7 (depends on 1)

The compound of claim 1, wherein T is NO or NO.sub.2.

### Claim 8 (depends on 1)

The compound of claim 1, wherein T is SO.sub.3 H, CH.sub.3 SO.sub.2, C.sub.2 H.sub.5 SO.sub.2 or C.sub.6 H.sub.5 SO.sub.2.

### Claim 9 (depends on 1)

The compound of claim 1, wherein T is CHO, CH.sub.3 CO, C.sub.2 H.sub.5 CO or C.sub.6 H.sub.5 CO.

### Claim 10 (depends on 1)

The compound of claim 1, wherein T is CN.

### Claim 11 (depends on 1)

The compound of claim 1, wherein T is --CH.dbd.B, wherein B is as defined above.

### Claim 12 (depends on 1)

The compound of claim 1, wherein R.sup.6 is cyano.

### Claim 13 (depends on 1)

The compound of claim 1, wherein R.sup.6 is carbamyl.

### Claim 14 (depends on 1)

The compound of claim 1, wherein R.sup.6 is nitro.

### Claim 15 (depends on 1)

The compound of claim 1, wherein R.sup.6 is acetyl.

### Claim 16 (depends on 1)

The compound of claim 1, wherein R.sup.6 is alkoxycarbonyl.

### Claim 17 (depends on 1)

The compound of claim 1, wherein R.sup.6 is selected from the group consisting of aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, diethylaminocarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec.-butoxycarbonyl, methoxyethoxycarbonyl, ethoxyethoxycarbonyl, n-propoxyethoxycarbonyl, isopropoxyethoxycarbonyl, n-butoxyethoxycarbonyl, isobutoxyethoxycarbonyl and sec.-butoxyethoxycarbonyl.