IP Library Granted Patent US 7,358,345
Granted Patent B2
US 7,358,345 · App. 10/575,599 · Granted Apr 15, 2008

Disperse azo dyestuffs

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Quick Facts
Patent No.
US 7,358,345
App. No.
10/575,599
Granted
Apr 15, 2008
Kind
B2
Abstract

The present invention claims dyestuffs of formula (I), wherein D, R 1 to R 7 and n are defined as given in claim 1 , a process for their preparation and their use

Claims (83)

1. Dyestuff of the formula I

wherein

D is a group of the formula (IIa)

wherein

T 1 , T 2 and T 3 are, independently, hydrogen, halogen or nitro;

T 4 is hydrogen, halogen, cyano or nitro;

wherein at least one of T 1 , T 2 , T 3 and T 4 is not hydrogen;

or a group of the formula (IIb)

wherein

T 5 is hydrogen or halogen; and

T 6 is hydrogen, —SO 2 CH 3 , —SCN or nitro;

wherein at least one of T 5 and T 6 is not hydrogen;

or a group of the formula (IIc)

or a group of the formula (IId)

wherein

T 7 is nitro, —CHO or a group of the formula

wherein T 10 is —H, halogen, nitro and cyano;

T 8 is hydrogen or halogen; or

T 9 is nitro, cyano, —COCH 3 or —COOT 10′ , wherein T 10′ is (C 1 -C 4 )-alkyl;

or a group of the formula (IIe)

R 1 is hydrogen, (C 1 -C 4 )-alkyl or —NHCOR 6 , where R 6 is (C 1 -C 4 )-alkyl or phenyl;

R 2 is unsubstituted (C 1 -C 6 )-alkyl, substituted (C 1 -C 6 )-alkyl, benzyl or phenylethyl and wherein said substituted (C 1 -C 6 )-alkyl is substituted by hydroxyl, (C 1 -C 4 )-alkoxy or halogen;

R 3 is hydrogen or methyl;

R 4 is hydrogen or methyl;

R 5 is hydrogen, methyl or phenyl;

R 7 is hydrogen, chloro, methoxy or ethoxy;

n is 0, 1 or 2;

s is 0 or 1;

with the proviso that

in the case R 1 , R 3 , R 4 , R 5 and R 7 are hydrogen and n=0

D is a group of the formula (IIc), (IId), (IIe) or (IIa) wherein T 1 is not nitro

if T 2 , T 3 and T 4 are hydrogen,

if T 2 and T 3 are hydrogen and T 4 is chlorine or cyano and

if T 2 and T 4 are hydrogen and T 3 is chlorine; and

with the further proviso that

in the case R 1 is methyl, R 3 , R 4 , R 5 and R 7 are hydrogen and n=0 then

R 2 is unsubstituted (C 1 -C 6 )-alkyl.

2. Dyestuff according to claim 1 of the formula (Ia)

wherein

D is a group of the formulae (IIa), (IIb), (IIc), (IId) or (IIe);

R 1 is (C 1 -C 4 )-alkyl;

R 2 is unsubstituted (C 1 -C 6 )-alkyl, benzyl or phenylethyl; and

n is 0, 1 or 2.

3. Dyestuff according to claim 1 of the formula (Ib)

wherein

T 3′ is bromo or chloro; and

R 2 is unsubstituted (C 1 -C 6 )-alkyl, substituted (C 1 -C 6 )-alkyl, benzyl or phenylethyl and wherein said substituted (C 1 -C 6 )-alkyl is substituted by hydroxyl, (C 1 -C 4 )-alkoxy or halogen.

4. Dyestuff according to claim 1 of the formula (Ic)

wherein

D is a group of the formulae (IIa), (IIb), (IIc), (IId) or (IIe);

R 1 is hydrogen, (C 1 -C 4 )-alkyl or —NHCOR 6 , where R 6 is (C 1 -C 4 )-alkyl or phenyl;

R 2 is unsubstituted (C 1 -C 6 )-alkyl, substituted (C 1 -C 6 )-alkyl, benzyl or phenylethyl and wherein said substituted (C 1 -C 6 )-alkyl is substituted by hydroxyl, (C 1 -C 4 )-alkoxy or halogen; and

R 3 is hydrogen and R 4 is methyl or R 3 is methyl and R 4 is hydrogen.

5. Dyestuff according to claim 1 of the formula (Id)

wherein

D is a group of the formulae (IIa), (IIb), (IIc), (IId) or (IIe);

R 1 is hydrogen, (C 1 -C 4 )-alkyl or —NHCOR 6 , where R 6 is (C 1 -C 4 )-alkyl or phenyl;

R 2 is unsubstituted (C 1 -C 6 )-alkyl, substituted (C 1 -C 6 )-alkyl, benzyl or phenylethyl and wherein said substituted (C 1 -C 6 )-alkyl is substituted by hydroxyl, (C 1 -C 4 )-alkoxy or halogen; and

R 5 is methyl or phenyl.

6. Dyestuff according to claim 1 of the formula (Ie)

wherein

D is a group of the formulae (IIa), (IIb), (IIc), (IId) or (IIe);

R 2 is unsubstituted (C 1 -C 6 )-alkyl, substituted (C 1 -C 6 )-alkyl, benzyl or phenylethyl and wherein said substituted (C 1 -C 6 )-alkyl is substituted by hydroxyl, (C 1 -C 4 )-alkoxy or halogen;

R 6 is (C 1 -C 4 )-alkyl or phenyl;

R 7 is chloro, methoxy or ethoxy; and

n is 0, 1 or 2.

7. Dyestuff according to claim 1 of the formula (If)

wherein

R 2 is unsubstituted (C 1 -C 6 )-alkyl, substituted (C 1 -C 6 )-alkyl, benzyl or phenylethyl and wherein said substituted (C 1 -C 6 )-alkyl is substituted by hydroxyl, (C 1 -C 4 )-alkoxy or halogen;

R 8 is nitro; and

n is 0, 1 or 2.

8. Dyestuff according to claim 1 of the formula (Ig)

wherein

D is a group of the formulae (IIa), (IIb), (IIc), (IId) or (IIe);

R 1 is hydrogen, (C 1 -C 4 )-alkyl or —NHCOR 6 , where R 6 is (C 1 -C 4 )-alkyl or phenyl;

R 2 is unsubstituted (C 1 -C 6 )-alkyl, substituted (C 1 -C 6 )-alkyl, benzyl or phenylethyl and wherein said substituted (C 1 -C 6 )-alkyl is substituted by hydroxyl, (C 1 -C 4 )-alkoxy or halogen; and

R 3 is hydrogen or methyl.

9. Process for the preparation of a dyestuff as claimed in claim 1 , which comprises diazotizing an amine of the formula III

D-NH 2   (III)

wherein D is a group of the formulae (IIa), (IIb), (IIc), (IId) or (IIe),

and coupling onto a compound of the formula IV

wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 7 are defined in claim 1 .

10. A process for dyeing and printing of synthetic textile material and fibre blends thereof which comprises contacting the dyestuff as claimed in claim 1 with the material.

Assignments (3)
MERGER Recorded Jun 26, 2012
From: DYSTAR COLOURS DEUTSCHLAND GMBH
To: DYSTAR COLOURS DISTRIBUTION GMBH
Reel/Frame 028440/0305 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2010
From: DYSTAR TEXTILFARBEN GMBH & CO. DEUTSCHLAND KG
To: DYSTAR COLOURS DEUTSCHLAND GMBH
Reel/Frame 025204/0348 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 17, 2006
From: HALL, NIGEL
To: DYSTAR TEXTLLFARBEN GMBH & CO. DEUTSCHLAND KG
Reel/Frame 017641/0639 →