Primary intermediates for oxidative coloration of hair
View Patent ↗Primary intermediates for hair coloring compositions for oxidative dyeing of hair are compounds of the formula (1): where R 1 and R 2 are each individually selected from a hydrogen atom, a C 1 to C 3 alkyl group, a C 1 to C 5 mono or dihydroxyalkyl group, phenyl or benzyl optionally substituted with an alkoxy group, or R 1 and R 2 together with the nitrogen atom to which they are attached form a piperazine, piperidine, imidazole, or morpholine ring.
1. A process for the preparation of a compound of formula (1) comprising (a) reductively aininating a compound of formula (2):
with a reagent of the formula R 1 R 2 NH and a reducing agent to produce a compound of formula (3)
and (b) subjecting the compound of formula (3) to catalytic hydrogenation to produce a compound of formula (1)
wherein R 1 and R 2 are each individually selected from the group consisting of hydrogen atom, a C 1 to C 5 alkyl group, a C 1 to C 5 mono or dihydroxyalkyl group, phenyl or benzyl optionally substituted with a hydroxyl, amino or C 1 to C 3 alkoxy group, or R 1 and R 2 together with the nitrogen atom to which they are bound form a C 3 to C 6 saturated or unsaturated ring, optionally containing in the ring one or more additional hetero atoms selected from O, S and N atoms.
2. A process according to claim 1 wherein R 1 and R 2 are each individually selected from the group consisting of hydrogen atom, a C 1 to C 3 alkyl group, phenyl or benzyl optionally substiuted with an alkoxy group, or R 1 and R 2 together with the nitrogen atom to which they are bound form a piperazine, piperidine, imidazols, imidazoline, pyridine, or morpholine ring.
3. A process according to claim 1 wherein R 1 is hydrogen and R 2 is phenyl.
4. A process according to claim 1 wherein R 1 and R 2 together with the nitrogen atom to which they are attached form a piperidine ring.
5. A hair dye product comprising a hair dyeing composition containing at least one primary intermediate and at least one coupler and a developer composition containing one or more oxidizing agents, the hair dyeing composition containing a primary intermediate comprising a compound of formula (1):
wherein R 1 and R 2 are each individually selected from the group consisting of hydrogen atoms, C 1 to C 3 alkyl, C 1 to C 3 mono or dihydroxyalkyl, phenyl or beazyl optionally substituted with a hydroxyl, amino or C 1 to C 3 alkoxy group, or R 1 and R 2 together with the nitrogen atom to which they are attached form a C 3 to C 6 saturated or unsaturated ring optionally containing in the ring one or more additional hetero atoms selected from O, S and N atoms.
6. A hair dye product to claim 5 wherein the hair dyeing composition additionally comprises a primary intermediate selected from the group consisting of: 2-methyl-benzene-1,4-diamine, benzene-1,4-diamine, 2-(2,5-diamino-phenyl)-ethanol, 1-(2,5-diamino-phenyl)-ethanol, 2-[4-amino-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol, 4-amino-phenol, 4-methylamino-phenol, 4-amino-3-methyl-phenol, 1-(5-amino-2-hydroxy-phenyl)-ethane-1,2-diol, 2-amino-phenol, 2-amino-5-methyl-phenol, 2-amino-6-methyl-phenol, N-(4-amino-3-hydroxy-phenyl)-acetamide, pyrimidine-2,4,5,6-tetramine, 2-(4,5-diamino-1H-pyrazol-1-yl)ethanol, 1-(4-methylbenzyl)-1H-pyrazole-4,5-diamine, and 1-(benzyl)-1H-pyrazole-4,5-diamine.
7. A hair dye product according to claim 5 wherein the coupler present in the hair dyeing composition is selected from the group consisting of: benzene-1,3-diol, 4-chlorobenzene-1,3-diol, naphthalen-1-ol, 2-methyl-naphthalen-1-ol, 2-methyl-benzene-1,3-diol, 2-(2,4-diamino-phenoxy)-ethanol, 2-(3-amino-4-methoxy-phenylamino)-ethanol, 2-[2,4-diamino5-(2-hydroxy-ethoxy)-phenoxy]-ethanol, and 3-(2,4-diamino-phenoxy)-propan-1-ol, 3-amino-phenol, 5-amino-2-methyl-phenol, 5-(2-hydroxy-ethylamino)-2-methyl-phenol, 3-amino-2-methyl-phenol, 3,4-dihydro-2H-1,4-benzoxazin-6-ol, 4-methyl-2phenyl-2,4-dihydro-3H-pyrazol-3-one, 1H-indol-6-ol, and 2-aminopyridin-3-ol.
8. A hair dye product according to claim 7 wherein the hair dyeing composition additionally comprises a primary intermediate selected from the group consisting of: 2-methyl-benzene-1,4-diamine, benzene-1,4-diamine, 2-(2,5-diamino-phenyl)-ethanol, 1-(2,5-diamino-phenyl)-ethanol, 2-[(4-amino-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol, 4-amino-phenol, 4-methylamino-phenol, 4-amino-3-methyl-phenol, 1-(5-amino-2-hydroxy-phenyl)-ethane-1,2-diol, 2-amino-phenol, 2-amino-5-methyl-phenol, 2-amino-6-methyl-phenol, N-(4-amino-3-hydroxy-phenyl)-acetamide, pyrimidine-2,4,5,6-tetramine, 2-(4,5-diamino-1H-pyrazol-1-yl)ethanol, 1-(4-methylbenzyl)-1H-pyrazole-4,5-diamine, and 1-(benzyl)-1H-pyrazole-4,5-diamine.
9. A hair dye product according to claim 5 wherein R 1 and R 2 are each individually selected from the group consisting of hydrogen atom, a C 1 to C 3 alkyl group, phenyl or beuzyl optionally substituted with an alkoxy group, or R 1 and R 2 together with the nitrogen atom to which they are bound form a piperazine, piperidine, imidazole, or morphoilne ring.
10. In a hair dyeing system wherein at least one primary intermediate is reacted with at least one coupler in the presence of an oxidizing agent to produce an oxidative hair dye, the improvement wherein the a least one primary intermediate comprises a compound of the formula (1):
wherein R 1 and R 2 are each individually selected from the group consisting of hydrogen atoms, C 1 to C 5 alkyl, C 1 to C 5 mono or dihydroxyalkyl, phenyl or benzyl optionally substituted with a hydroxyl, amino or C 1 to C 3 alkoxy group, or R 1 and R 2 together with the nitrogen atom to which they are attached form a C 3 to C 6 saturated or unsaturated ring optionally containing in the ring one or mare additional hetero atoms selected from O, S and N atoms.
11. A system for coloring hair according to claim 10 wherein R 1 and R 2 are each individually selected from the group consisting of hydrogen atom, a C 1 to C 3 alkyl group, phenyl or beunyl optionally substituted with an alkoxy group, or R 1 and R 2 together with the ninogen atom to which they are bound farm a piperazine, piperidine, imidazole, or morphoilne ring.
12. A hair dyeing composition comprising, In a suitable carrier or veluicle an effectivc hair dyeing amount of:
(a) at least one coupler, and
(b) at least one primary intermediate comprising a compound of the formula (1):
wherein R 1 and R 1 are each individually selected from the group consisting of hydrogen atoms, C 1 to C 5 alkyl, C 1 to C 5 mono or dihydroxyalkyl, phenyl or benzyl optionally substituted with a hydroxyl, amino or C 1 to C 3 alkoxy group, or R 1 and R 2 together with the nitrogen atom to which they are attached form a C 3 to C 6 saturated or unsaturated ring optionally containing in the ring one or more additional hetero atoms selected from O, S and N atoms.
13. A hair dyeing composition according to claim 12 comprising a primary intermediate selected from the group consisting of: 2-methyl-benzene-1,4-diamine, benzene-1,4-diamine, 2-(2,5-diamino-phenyl)-ethanol, 1-(2,5-diamino-phenyl)-ethanol, 2-[(4-amino-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol, 4-amino-phenol, 4-methylamino-phenol, 4-amino-3-methyl-phenol, 1-(5-amino-2-hydroxy-phenyl)-ethane-1,2-diol, 2-amino-phenol, 2-amino-5-methyl-phenol, 2-amino-6-methyl-phenol, N-(4-amino-3-hydroxy-phenyl)-acetamide, pyrimidine-2,4,5,6-tetramine, 2-(4,5-diamino-1H-pyrazol-1-yl)ethnol, 1-(4-methylbenzyl)-1H-pyrazole-4,5-diamine, and 1-(benzyl)-1H-pyrazole-4,5-diamine.
14. A hair dyeing composition according to claim 12 wherein the at least one coupler is selected from the group consisting of: benzene-1,3-diol, 4-chlorobenzene-1,3-diol, naphthalen-1-ol, 2-methyl-naphthalen-1-ol, 2-methyl-benzene-1,3-diol, 2-(2,4-diamino-phenoxy)-ethanol, 2-(3-amino-4-methoxy-phenylamino)-ethanol, 2-[2,4-diamino-5-(2-hydroxy-ethoxy)-phenoxy]-ethanol, and 3-(2,4-diamino-phenoxy)-propan-1-ol, 3-amino-phenol, 5-amino-2-methyl-phenol, 5-(2-hydroxy-ethylamino)-2-methyl-phenol, 3-amino-2-methyl-phenol, 3,4-dihydro-2H-1,4-benzoxazin-6-ol, 4-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, 1H-indol-6-ol, and 2-aminopyridin-3-ol.
15. A hair dyeing composition according to claim 14 additional comprising a primary intermediate selected from the group consisting of: 2-methyl-benzene-1,4-diamine, benzene-1,4-diamine, 2-(2,5-diamino-phenyl)-ethanol, 1-(2,5-diamino-phenyl)-ethanol, 2-[(4-amino-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol, 4-amino-phenol, 4-methylamino-phenol, 4-amino-3-methyl-phenol, 1-(5-amino-2-hydroxy-phenyl)-ethane-1,2-diol, 2-amino-phenol, 2-amino-5-methyl-phenol, 2-amino-6-methyl-phenol, N-(4-amino-3-hydroxy-phenyl)-acetamide, pyrimidine-2,4,5,6-tetramine, 2-(4,5-diamino-1H-pyrazol-1-yl)ethanol, 1-(4-methylbenzyl)-1H-pyrazole-4,5-diamine, and 1-(benzyl)-1H-pyrazole-4,5-diamine.
16. A hair dyeing composition of claim 12 wherein R 1 and R 2 are each individually selected from the group consisting of hydrogen atom, a C 1 to C 3 alkyl group, phenyl or beuzyl optionally substituted with an alkoxy group, or R 1 and R 2 together with the nitrogen atom to which they are bound form a piperazine, piperidine, imidazole, or morpholine ring.
17. A prcoess for dyeing hair comprising firming a hair dye product composition by mixing a developer composition and a hair dyeing composition as defined in claim 12 , applying to the hair an amount of the hair dye product composition effective to dye the hair, permitting the hair dye product composition to contact the hair for period of titm effective to dye the hair, and removing the hair dye product composition from the hair.
18. A process according to claim 17 wherein R 1 and R 2 are each individually selected from the group consisting of hydrogen atom, a C 1 to C 3 alkyl group, phenyl or benayl optionally substituted with an alkoxy group, or R 1 and R 2 together with the nitrogen atom to which they am bound form a piperazine, piperidine, imidazole, or mompholino ring.