N-Aminoalkylenesulfonamido substituted monoazo colorants

• US 4,379,088 A
• Filed: 08/17/1981
• Issued: 04/05/1983
• Est. Priority Date: 10/08/1980
• Status: Expired due to Fees

• Current Assignee: PMD Holdings Corporation (Berkshire Hathaway Incorporated)
• Original Assignee: Sterling Drug, Inc. (GSK plc)
• Inventors: Crounse, Nathan N.
• Primary Examiner(s): Doll, John
• Application Number:
  US06/293,393
• Time in Patent Office: 596 Days
• Field of Search: 260/157, 260/200, 260/201
• US Class Current: 534/864
• CPC Class Codes: C09B 29/103 of the naphthalene series
• CPC Class Codes: C09B 35/18 from heterocyclic compounds
• CPC Class Codes: C09B 35/28 the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O—

Abstract

This invention relates to novel mixtures consisting essentially of monoazo compounds and disazo compounds which are substituted with x (N-substituted sulfonamido) groups, to acid-addition salts of said azo compounds, useful as direct dyes particularly in the dyeing of cellulose, and to methods of preparation of said mixtures of (N-substituted sulfonamido) substituted monoazo and disazo compounds.

Claims

1. A mixture consisting essentially of a monoazo compound which is substituted with an average of x (N-substituted sulfonamido) groups per molecule wherein said monoazo compound is of the formula ##STR25## in which x represents a number from 1 to 4,

R represents hydrogen or the moiety ##STR26## in which R⁴ is hydrogen, C₁ to C₃ alkoxy or C₁ to C₃ alkyl,

R¹ represents a moiety selected from the group consisting of

alkylene-NH-alkylene-NH₂,

alkylene-N-(C₁ to C₄ alkyl)₂, ##STR27## in which alkylene represents --CH₂ CH₂ -- and --CH₂ CH₂ CH₂ --,

R³ represents hydrogen, C₁ to C₃ alkyl or C₁ to C₃ alkoxy;

or

the acid-addition salt forms of said mixtures of monoazo compounds.

2. A mixture according to claim 1 wherein the monoazo compound is of the formula ##STR28## in which R¹, R³, R⁴ and x each have the same respective meanings given in claim 1.

3. The mixture according to claim 2 wherein R¹ is --(CH₂)₃ N(CH₃)₂ and R³ and R⁴ are each methoxy.

4. A mixture according to claim 2 wherein the monoazo compound is of the formula ##STR29## in which R¹, R³ and x each have the same respective meanings given in claim 2.

5. The mixture according to claim 4 wherein R¹ is --(CH₂)₃ N(CH₃)₂ and R³ is 2-methoxy.

6. The mixture according to claim 4 wherein R¹ is --(CH₂)₃ N(CH₃)₂ and R³ is 4-methoxy.

7. The mixture according to claim 4 wherein R¹ is ##STR30##

8. The mixture according to claim 4 wherein R¹ is ##STR31##

9. The mixture according to claim 4 wherein R¹ is --(CH₂)₂ NH(CH₂)₂ NH₂ and R³ is 2-methoxy.

10. The mixture according to claim 4 wherein R¹ is --(CH₂)₂ NH(CH₂)₂ NH₂ and R³ is 4-methoxy.