Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1985-12-12
1988-06-28
Hollrah, Glennon H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
8410, 8416, C07C14942, A61K 713
Patent
active
047540699
DESCRIPTION:
BRIEF SUMMARY
The subject matter of the invention are compositions for the oxidative dyeing of hair on the basis of developing and coupler substances, whereby novel 2-alkyl sulfonyl-1,4-diaminobenzenes are used as the coupler substance.
Oxidation dyes have reched a substantial importance for hair dyeing. The dyeing is thereby generated by the reaction of specific developing substances with specific coupler substances in the presence of a suitable oxidation agent.
Preferably 2,5-diaminotoluene, 4-aminophenol and 1,4-diaminobenzene are used as developing substances, however 2,5-diaminoanisol, 2,5-diaminobenzyl alcohol and 2-(.beta.-hydroxyethyl)1,4-diaminobenzene have attained a certain importance. Tetraaminopyrimidine may also be used as a developing substance in certain cases.
For generating natural shades mainly resorcinol or 4-chlororesorcinol are used as coupler substances in conjunction with m-aminophenol. Instead of resorcinol one can also use 4-hydroxy-1,2-methylene dioxybenzene or 4-amino-1,2-methyllene dioxybenzene. Preferably 2,4-diamino phenol ether like 2,4-diaminoanisol, 2,4-diaminophenetol, 2,4-diamino phenoxy ethanol and 2-amino-4-(2'-hydroxyethylamino)-anisol are used for generating of blue constituents in black and ash shades. Furthermore, specific pyridine derivatives like, for example, 3,5-diamino-2,6-dimethoxy pyridine may be used as blue couplers. In addition to the mentioned compounds the coupler substances 4,6-dichlororesorcinol, 2-methyl resorcinol, 2,4-dihydroxy anisol, 5-amino-2-methylphenyl-1-naphtol, 4-aminohydroxy phenoxy ethanol and 4-hydroxyindol are of interest as shaders.
The described dye systems on the basis of the mentioned developing and coupler substances has been proven in practice, but it has some disadvantages which must be removed. For example, hair dyes are generated during the oxidative hair dyeing with the developing substances, 2,5-diaminotoluol or 1,4-diaminotoluene in combination with the coupler substances resorcinol or chlororesorcinol which do not appear natural, but show rusty appearing reflexes. As is known the desire for a natural hair coloring is particularly very well pronounced with women having heavily graying hair. This desire cannot be met sufficiently with the known oxidation hair dyeing compositions.
It had been repeatedly tried to remove the described disadvantages of the developing substances 2,5-diaminotoluene and 1,4-diaminobenzene, in that the hydrogen atoms on the amino groups of these molecules are substituted by specific residues, for example, carbamoyl methyl or hydroxyethyl. However, generally such substitution resulted in developing substances with degenerated dye characteristics. This degeneration shows in an insufficient dye balance and/or the complete missing of the formation of natural shades when using the customary developer in combination with resorcinol, 4-chlororesorcinol, 4-6-dichlororesorcinol, 4-hydroxy-1,2-methylene dioxybenzene and 4-amino-1,2-methylenedioxybenzene as coupler substances.
Surprisingly, it now had been found that, when replacing a hydrogen atom on the benzene core of the 1,4-diaminobenzene with an alkyl sulfonyl ethyl residue, the aforementioned disadvantages do not exist. These novel developing substances result in very natural appearing blond to brown color shades in combination with the coupler substances resorcinol, 4-chlororesorcinol, 4,6-dichlororesorcinol, 4-hydroxy-1,2-methylene dioxybenzene and 4-amino-1,2-methylene dioxybenzene.
Therefore, the subject matter of the present patent application are 2-alkyl sulfonyl ethyl-1,4-diamonobenzenes of formula I ##STR2## wherein R denotes CH.sub.3 or C.sub.2 H.sub.5, and the salts thereof as well as compositions for the oxidative dyeing of human hair on the basis of a developing substance-coupler substance combination, which contain as the developing substance a composition of formula I or the salts thereof.
The making of the novel 2-alkyl sulfonyl ethyl-1,4-diaminobenzenes is advantageously performed in eight synthesis steps in accordance with the following reaction patte
REFERENCES:
patent: 3118943 (1964-01-01), Buc et al.
patent: 3326979 (1967-06-01), Russell et al.
patent: 3687567 (1972-09-01), Shen et al.
Braun Hans-Jurgen
Konrad Eugen
Mager Herbert
Hollrah Glennon H.
Sopp John A.
Striker Michael J.
Wella Aktiengesellschaft
LandOfFree
2-alkyl sulfonyl-1,4-diaminobenzenes, processes for their produc does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with 2-alkyl sulfonyl-1,4-diaminobenzenes, processes for their produc, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 2-alkyl sulfonyl-1,4-diaminobenzenes, processes for their produc will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1915888