Cationic azo monomers or symmetric dimers, preparation thereof, compositions comprising same and process for dyeing keratin fibers
A compound and heteroatom technology, applied in the field of human keratin material, human keratin fiber dyeing, and human keratin fiber field, can solve the problem that the dye is not very resistant to washing, etc.
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Embodiment 1
[0307] compound 1 Synthesis of: 8-{(E)-[4-({4-chloro-6-[4-{(E)-[2-hydroxy-7-(trimethylammonium (ammonio)-1-naphthyl] -diazenyl}phenyl)amino]-1,3,5-triazin-2-yl}amino)-phenyl]diazenyl}-7-hydroxy-N,N,N-trimethyl Naphthalene-2-dichloroammonium.
[0308]
[0309] Basic brown 16 dye (20 g) was dissolved in 200 ml of water. The resulting solution was slowly added to a solution containing cyanuric chloride (0.5 mol eq.), acetone (30 ml) and ice (50 g).
[0310] During the addition, the temperature was maintained at 0 to 5°C using a water bath of ice-water mixture. Solid sodium bicarbonate was added to maintain the pH between 3 and 6.
[0311] After mixing, the reaction mixture was maintained at 40°C for 1 hour with constant agitation, then at 50°C for 6 hours.
[0312] Stabilization of the pH indicates completion of the reaction.
[0313] The reaction mixture was left at room temperature for 16 hours without constant agitation to give a fine precipitate which was filtered of...
Embodiment 2 and 3
[0316] compound 2 Synthesis of: 7-hydroxy-8-{(E)-[4-({4-[(2-hydroxyethyl)amino]-6-[(4-{(E)-[2-hydroxy-7- (Trimethyl Ammonium (ammonio))-1-naphthyl]diazenyl}phenyl)amino]-1,3,5-triazin-2-yl}amino)phenyl]diazenyl}-N,N,N - Ammonium trimethylnaphthyl-2-dicarboxylate.
[0317] compound 3 Synthesis of: 7-Hydroxy-8-{(E)-[4-({4-Hydroxy-6-[4-{(E)-[2-Hydroxy-7-(Trimethyl Ammonium (ammonio))-1-naphthyl]diazenyl}phenyl)amino]-1,3,5-triazin-2-yl}-amino)phenyl]diazenyl}-N,N, Ammonium N-trimethylnaphthyl 2-dicarboxylate.
[0318]
[0319] The compound obtained above 1 (1g) was dissolved in 100ml of water, and monoethanolamine (1g) was added.
[0320] After the addition, the reaction mixture was kept at 90°C for 48 hours with constant agitation, then the solvent was evaporated to dryness.
[0321] A sample of the reaction mixture was purified by chromatography while performing counter ion exchange (Cl - to CH 3 COO - ).
[0322] Dye 2 is thus obtained, where R represents NHCH...
Embodiment 4
[0324] compound 4 Synthesis of: 8-((E)-{4-[(4,6-dipyrrolidin-1-yl-1,3,5-triazin-2-yl)amino]phenyl}-diazenyl )-7-hydroxy-N,N,N-trimethylnaphthyl-2-ammonium chloride.
[0325]
[0326] Intermediate compound 1 was obtained by the following method:
[0327] As in Example 1, basic brown 16 dye (20 g) was dissolved in 200 ml of water. The resulting solution was slowly added to a solution containing cyanuric chloride (0.5 mol eq.), acetone (30 ml) and ice (50 g).
[0328] During the addition, the temperature was maintained at 0 to 5°C using a water bath of ice-water mixture. Solid sodium bicarbonate was added to maintain the pH between 3 and 6.
[0329] Stabilization of the pH indicates completion of the reaction.
[0330] Next, the product was precipitated with acetone, and the precipitate was filtered off and finally vacuum dried in a desiccator.
[0331] Proton NMR spectroscopy and mass spectrometry confirmed that intermediate compound I had been obtained.
[0332] Interme...
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