Soluble trisazo dyestuffs containing a 2-phenyl-benzimidazolyl, -benzoxazolyl or -benzthiazolyl middle component

• US 4,144,231 A
• Filed: 05/10/1977
• Issued: 03/13/1979
• Est. Priority Date: 05/19/1976
• Status: Expired due to Term

• Current Assignee: Cassella Aktiengesellschaft (Sanofi )
• Original Assignee: Cassella Aktiengesellschaft (Sanofi )
• Inventors: Bauer, Wolfgang, Ribka, Joachim
• Primary Examiner(s): Warren, Charles F.
• Application Number:
  US05/795,435
• Time in Patent Office: 672 Days
• Field of Search: 260/157, 260/158, 260/155, 260/156, 260/159
• US Class Current: 534/665
• CPC Class Codes: C09B 35/376 D is a heterocyclic compound
• CPC Class Codes: D06P 1/06 containing acid groups

Abstract

A water soluble trisazo dyestuff of the formula B₁ --N═N--Z-N═N-M-N═N-B₂ is useful for dyeing substances containing nitrogen or hydroxyl wherein M is ##STR1## B₁ and B₂ are the same or different and are selected from the group consisting of ##STR2## 2,4-dihydroxy-3-quinolyl and 2,6-diamino-5-pyridyl; Z is ##STR3## X is --O-- or --S--; R₁ is hydrogen, alkyl having 1 to 4 carbon atoms, phenyl or benzyl; R₃ is hydrogen, chloro or alkyl or alkoxy having 1 to 4 carbon atoms;

R₄ is hydrogen chloro, alkyl or alkoxy having 1 to 4 carbon atoms, hydroxy, alkanoylamino having 1 to 4 carbon atoms, benzoylamino, naphthoylamino, oxalylamino, carboxyalkylamino having 2 to 5 carbon atoms, sulphoalkylamino having 1 to 4 carbon atoms or oxyalkylamino having 1 to 4 carbon atoms;

R₅ is hydrogen or alkyl having 1 to 8 carbon atoms; R₆ is --CN, --COOH, --CONH₂ or --SO₃ H; R₇ is hydrogen, or alkyl having 1 to 4 carbon atoms, R₈ is hydrogen phenyl or phenyl substituted with a methyl, nitro, chloro or sulpho; R₉ is methyl, carboxyl or alkoxycarbonyl having 2 to 5 carbon atoms; R₁₀ is hydrogen, methyl, methoxy, chloro, --COOH or --SO₃ H;

E is a hydroxyl, amino, alkylamino having 1 to 4 carbon atoms, phenylamino, naphthylamino, benzoylamino, naphthoylamino, alkanoylamino having 2 to 5 carbon atoms, carboxyalkylamino having 2 to 5 carbon atoms, sulphoalkylamino having 1 to 4 carbon atoms, hydroxyalkylamino having 1 to 4 carbon atoms dialkylamino having 1 to 4 carbon atoms in each alkyl;

E'"'"' is hydrogen or the same or a different member of the group of substituents standing for E;

R₁₁, r₁₂ and R₁₃ are alkyl or alkoxy having 1 to 4 carbon atoms, carboxyl, sulpho, chloro, bromo, nitro or methoxycarbonyl; R₁₄ and R₁₅ are hydrogen, methyl, ethyl, methoxy, ethoxy or chloro; with the proviso that at least one of M, B₁ and B₂ includes a sulpho substituent.

Claims

1. A water soluble trisazo dyestuff of the formula

View Dependent Claims (3, 4, 5, 7, 8, 9, 10, 11, 12, 13, 14)

3. substituent. 2. A water soluble trisazo dyestuff of claim 1 wherein B₁, B₂ or both is ##STR41##

4. A water soluble trisazo dyestuff of claim 1 wherein B₁, B₂ or both is ##STR42##

5. A water soluble trisazo dyestuff of claim 1 wherein B₁, B₂ or both is ##STR43##

7. A water soluble trisazo dyestuff of claim 5 wherein B₁, B₂ or both is ##STR48##

8. A water soluble trisazo dyestuff of claim 5 wherein B₁, B₂ or both is ##STR49##

9. A water soluble trisazo dyestuff of claim 5 wherein X is ##STR50##

10. A water soluble trisazo dyestuff of claim 5 wherein R₁₄ and R₁₅ are the same or different and are selected from the group consisting of hydrogen, chloro and methyl.

11. A water soluble trisazo dyestuff of claim 5 having from 2-4 sulpho substituents.

12. A water soluble trisazo dyestuff according to claim 5 having the formula ##STR51##

13. A water soluble trisazo dyestuff according to claim 5 having the formula ##STR52##

14. A water soluble trisazo dyestuff according to claim 5 having the formula ##STR53##

2. 4-dihydroxy-3-quinolyl and 2,6-diamino-5-pyridyl;

Z is ##STR39## X is ##STR40## --O-- or --S--;

R₁ is hydrogen, alkyl having 1 to 4 carbon atoms, phenyl or benzyl;

R₃ is hydrogen, chloro or alkyl or alkoxy having 1 to 4 carbon atoms;

R₄ is hydrogen chloro, alkyl or alkoxy having 1 to 4 carbon atoms, hydroxy, alkanoylamino having 1 to 4 carbon atoms, benzoylamino, naphthoylamino, oxalylamino, carboxyalkylamino having 2 to 5 carbon atoms, sulphoalkylamino having 1 to 4 carbon atoms or oxyalkylamino having 1 to 4 carbon atoms;

R₅ is hydrogen or alkyl having 1 to 8 carbon atoms;

R₆ is --CN, --COOH, --CONH₂ or --SO₃ H;

R₇ is hydrogen or alkyl having 1 to 4 carbon atoms;

R₈ is hydrogen, phenyl or phenyl substituted with a methyl, nitro, chloro or sulpho;

R₉ is methyl, carboxyl or alkoxycarbonyl having 2 to 5 carbon atoms;

R₁₀ is hydrogen, methyl, methoxy, chloro, --COOH or --SO₃ H;

E is a hydroxyl, amino, alkylamino having 1 to 4 carbon atoms, phenylamino, naphthylamino, benzoylamino, naphthoylamino, alkanoylamino having 2 to 5 carbon atoms, carboxyalkylamino having 2 to 5 carbon atoms, sulphoalkylamino having 1 to 4 carbon atoms, hydroxyalkylamino having 1 to 4 carbon atoms or dialkylamino having 1 to 4 carbon atoms in each alkyl;

E'"'"' is hydrogen or the same or a different member of the group of substituents standing for E,

R₁₁, r₁₂ and R₁₃ are alkyl or alkoxy having 1 to 4 carbon atoms, carboxyl, sulpho, chloro, bromo, nitro or methoxycarbonyl;

R₁₄ and R₁₅ are hydrogen, methyl, ethyl, methoxy, ethoxy or chloro;

with the proviso that at least one of M, B₁ and B₂ includes a sulpho

6. A water soluble trisazo dyestuff of the formula