Monoazo reactive dyes

• US 6,127,531 A
• Filed: 05/26/1999
• Issued: 10/03/2000
• Est. Priority Date: 05/30/1998
• Status: Expired due to Term

• Current Assignee: Clariant Finance (Bvi) Limited
• Original Assignee: Clariant Finance (Bvi) Limited
• Inventors: Nusser, Rainer
• Primary Examiner(s): POWERS, FIONA
• Application Number:
  US09/320,231
• Time in Patent Office: 496 Days
• Field of Search: 534/634, 534/635, 534/638, 534/797, 534/803
• US Class Current: 534/634
• CPC Class Codes: C09B 43/16 linking amino-azo or cyanuric acid residues
• CPC Class Codes: C09B 62/043 containing two or more triazine rings linked together by a non-chromophoric link
• CPC Class Codes: C09B 62/085 Monoazo dyes
• CPC Class Codes: C09B 62/245 Monoazo dyes

Abstract

A dyestuff according to formula (I) ##STR1## or a salt thereof wherein the substituents have the definitions as defined in claim 1.

The dyestuffs are useful for dyeing or printing nitrogen-containing or hydroxy-group-containing organic substrates and for the production of printing inks.

Claims

1. A dyestuff according to formula (I) ##STR43## or a salt thereof, wherein the sulphonic acid group can be in 3- or 4- or 5-position of the phenyl ring, preferably in the 4-position, and RG, which is bonded in the 2- or 3-position of the naphthalene ring, signifies ##STR44## wherein X and Y, independently from each other are a substituent which is selected from Cl, F, an amino group of the formula --NR₄ R₅ wherein R₄ and R₅ are independently hydrogen or C_1-4 alkyl, optionally substituted by OH, COOH or SO₃ H or a group A--SO₂ --B wherein A is a divalent group selected from C_2-3 alkylene, C_5-8 cycloalkylene or phenylene and B is a group selected from --CH═

CH₂, --CH═

CH--Z, --CH₂ CH₂ --Z or --CH(CH₂ Z)--CH₂ Z wherein Z is a group removable by alkali or R₄ and R₅ together with the nitrogen atom to which they are connected are a heterocycle having 4 to 8 carbon atoms optionally containing another hetero-atom selected from O, N or S or X is Cl or F and Y signifies a radical of formula (la) ##STR45## wherein W is C_1-6 alkylene and all the substituents have the same definition as defined above with the proviso that W connects two identical radicals.

2. A dyestuff according to claim 1 which corresponds to the formula (II) ##STR46## wherein X is chlorine or fluorine, Y is --NR₄ R₅ and R₄ and R₅ are together with the nitrogen atom to which they are connected a heterocycle having 4 to 8 carbon atoms optionally containing another hetero-atom selected from O, N or S;

or R₄ is hydrogen or C_1-4 alkyl and R₅ is C_1-4 alkyl or phenyl which both may be substituted by hydroxy, methyl or SO₃ H, or R₅ is a group --A--SO₂ --B as defined in claim 1.

3. A dyestuff according to claim 2 wherein X is fluoro and Y is the --NR₄ R₅ radical defined as β

-(β

'"'"'-(β

"-Chloroethyl-sulphonyl)-ethoxy)-ethylamino, 2-methylphenylamino, β

-Sulphoethylamino, γ

-(β

'"'"'-sulphoethylsulphonyl)-propylamino, morpholino, ethylamino, γ

-(β

'"'"'-sulphatoethylsulphonyl)-propylamino, methylamino, Bis N,N-(γ

-(β

'"'"'-sulphatoethylsulphonyl)-propyl)-amino, Bis N,N-(β

-(β

'"'"'chloroethylsulphonyl)-ethyl)-amino, N-phenyl-N-(β

-(β

'"'"'-sulphatoethylsulphonyl)-ethyl)-amino and N-phenyl-N-(γ

-(β

'"'"'-sulphatoethylsulphonyl)-propyl)-amino.

4. A dyestuff according to claim 2 wherein X is chloro and Y is the --NR₄ R₅ radical defined as β

-(β

'"'"'-(β

"-Chloroethyl-sulphonyl)-ethoxy)-ethylamino, 2-methylphenylamino, β

-Sulphoethylamino, γ

-(β

'"'"'-sulphoethylsulphonyl)-propylamino, morpholino, ethylamino, γ

-(β

'"'"'-sulphatoethylsulphonyl)-propylamino, methylamino, Bis N,N-(γ

-(β

'"'"'-sulphato-ethylsulphonyl)-propyl)-amino, BisN,N-(β

-(β

'"'"'chloroethylsulphonyl)-ethyl)-amino, N-phenyl-N-(β

-(β

'"'"'-sulphatoethylsulphonyl)-ethyl)-amino and N-phenyl-N-(γ

-(β

'"'"'-sulphatoethylsulphonyl)-propyl)-amino.

5. A dyestuff according to claim 3 wherein Y is the --NR₄ R₅ radical as morpholino.

6. A dyestuff according to claim 1 which corresponds to the formula (III) ##STR47## wherein the difluoropyrimidine is bonded to the 2 position of the naphthyl-ring.

7. A process of forming a dyestuff as defined in claim 1 comprising the step of reacting a dyestuff of the phenyl-azo-naphthalene series having a reactive amino-hydrogen atom with a reagent R_g --X wherein R_g is a labile-halogen-containing pyrimidine or triazinyl radical and X is a halogen selected from F, or Cl.

8. A process of dyeing or printing hydroxy-group-containing or nitrogen-containing organic substrates comprising applying thereto a dyestuff according to claim 1.

9. A process for the preparation of printing inks comprising mixing a dyestuff according to claim 1 into an aqueous composition suitable for ink jet printing.