The present invention relates to an azo dye of formula (I) wherein R 1 and R 2 are each independently of the other —NH—(CH 2 CH 2 )—OH, —NH—CH 2 —CHOH—CH 2 —OH, —NH—(CH 2 CH 2 )—S—(CH 2 CH 2 )—OH, —NH—(CH 2 CH 2 )—NH—(CH 2 CH 2 )—OH, NH—CH 2 CH 2 —CON(CH 2 CH 2 OH) 2 , R 3 is —CN or —CONH 2 , R 4 is methyl or trifluoromethyl, R 5 is —CF 3 , —COOC 2 H 5 , R 6 is hydrogen or chlorine and R 7 is hydrogen, chlorine, bromine or —NO 2 , to a process for the preparation thereof and to the use thereof in a method of producing mass-coloured plastics or polymeric colour particles
1. An azo dye of formula I
wherein
R 1 and R 2 are each independently of the other —NH—(CH 2 CH 2 )—OH, —NH—CH 2 —CHOH—CH 2 —OH, —NH—(CH 2 CH 2 )—S—(CH 2 CH 2 )—OH, —NH—(CH 2 CH 2 )—NH—(CH 2 CH 2 )—OH, —NH—(CH 2 CH 2 )—NH 2 , —NH—CH 2 —CHOH—CH 2 —NH 2 , —NH—CH 2 —CON(CH 2 CH 2 OH) 2 , —NH—CH 2 CH 2 —CON(CH 2 CH 2 OH) 2 ,
R 3 is —CN or —CONH 2 ,
R 4 is methyl or trifluoromethyl,
R 5 is —CF 3 , —COOC 2 H 5 ,
R 6 is hydrogen or chlorine, and
R 7 is hydrogen, chlorine, bromine or —NO 2 .
2. An azo dye of formula I according to claim 1 wherein R 3 is —CN and R 4 is methyl.
3. An azo dye of formula I according to claim 1 wherein R 1 and R 2 are
4. An azo dye of formula I according to claim 1 wherein R 7 is hydrogen.
5. An azo dye of formula Ia, Ib, Ic or Id
6. A process for the preparation of an azo dye of formula (I) according to claim 1 , which comprises diazotizing a compound of formula (II)
wherein R 5 , R 6 and R 7 are as defined in claim 1 , according to a conventional method and then coupling the diazotized compound with a coupling component of formula III
wherein R 1 , R 2 R 3 and R 4 are as defined in claim 1 .
7. A method of producing mass-coloured plastics or polymeric colour particles that comprises mixing a high molecular weight organic material with a tinctorially effective amount of at least one azo dye of formula (I) according to claim 1 .
8. A method of producing mass-coloured plastics or polymeric colour particles that comprises causing a mixture comprising at least one monomer that contains at least one NH-, CH or SH-reactive group and is capable of polymerisation, polyaddition or polycondensation reactions to react with at least one compound of formula I according to claim 1 .
9. Plastics or polymeric colour particles coloured in accordance with a method according to claim 7 .
10. Plastics or polymeric colour particles coloured in accordance with a method according to claim 8 .
11. A method of producing colour filters that comprises coating a substrate with a high molecular weight organic material that contains a tinctorially effective amount of at least one azo dye of formula (I) according to claim 1 .