Para-phenylene diamine compounds (I), their solvates and acid addition salts are new. Para-phenylene diamine compounds of formula (I), their solvates and acid addition salts are new.R 1R 2= combine to form 4-7 membered rings (containing carbon and two atoms of O or N) (optionally substituted). Provided that when the ring comprises two atoms of O or N, then the two atoms are in non-adjacent position. Provided that (I) is not 2,3-dihydro-benzo[1,4]dioxine-5,8-diamine, 3,4-dihydro-2H-benzo[b][1,4]dioxepine-6,9-diamine, 2-methyl-benzo[1,3]dioxole-4,7-diamine, 1,1-dimethyl-indan-4,7-diamine, 5,6,7,8-tetrahydro-naphthalene-1,4-diamine or bicyclo[4.2.0]octa-1,3,5-triene-2,5-diamine. Independent claims are included for: (1) the preparation of (I); (2) a diazo intermediate compound of formula (II); (3) a dye composition comprising (I) (except 2,3-dihydro-benzo[1,4]dioxine-5,8-diamine, 3,4-dihydro-2H-benzo[b][1,4]dioxepine-6,9-diamine or 2-methyl-benzo[1,3]dioxole-4,7-diamine) in a coloring medium; (4) a dyeing process of human keratinous fibers i.e. hair, comprising applying the dye composition on hair up to the development of a desired color, in air, using an oxidizing agent, optionally in the presence of an oxidation catalyst; and (5) a kit having several compartments comprising the dye composition in a first compartment and an oxidation composition in a second compartment. R 3 : H, sulfonic or 1-4C alkyl. Provided that (II) is not 4-phenylazo-5,6,7,8-tetrahydro-naphthalen-1-ylamine, 4-(4-butyl-phenylazo)-5,6,7,8-tetrahydro-naphthalen-1-ylamine or 4-(4-amino-5,6,7,8-tetrahydro-naphthalen-1-ylazo)-benzenesulfonic acid. [Image].
New primary 2,3-disubstituted para-phenylendiamins and their use as oxidative colouring of keratinic fibers