Substituted 2-aminoalky-1,4-diaminobenzene compounds and...

Details Substituted 2-aminoalky-1,4-diaminobenzene compounds and... Substituted 2-aminoalky-1,4-diaminobenzene compounds and...

2000-10-20

2002-08-20

Douyon, Lorna M. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S405000, C008S406000, C008S407000, C008S408000

Reexamination Certificate

active

06436152

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to compositions for dyeing keratin fibers based on a developer-coupler substance combination, which contain at least one substituted 2-aminoalkyl-1,4-diaminobenzene compound as the developer substance. It also relates to new substituted 2-aminoalkyl-1,4-diaminobenzene compounds.
2. Prior Art
Oxidation dye precursor compounds have been important in the field of dyeing keratin fibers, especially hair, for a long time. The dye compounds for dyeing the keratin fibers are produced by reaction of certain developer substances with certain coupler substances in the presence of a suitable oxidizing agent. The following compounds are examples of developer substances: 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol and 1,4-diaminobenzene. The following compounds are examples of coupler substances: resorcinol, 4-chlororesorcinol, 1-naphthol, 3-aminophenol and derivatives of m-phenylenediamines.
There are numerous additional requirements of oxidation dye precursor compounds for dyeing human hair besides the resulting color in the desired intensity. The dye precursor compounds must be unobjectionable in toxicological and dermatological respects and the resulting hair color of the dyed hair must have good light fastness, permanent wave fastness, acid fastness and rubbing fastness. The color produced by dyeing the hair with the oxidation dye precursor compounds must remain stable in the presence of light, rubbing and chemical agents for at least four to six weeks. Moreover a broad palette of various color shades can be produced by combination of suitable developer and coupler substances.
The requirements for oxidation dye precursor compounds however cannot be completely fulfilled in every way with the currently known dye precursor compounds, as has been stated in the Monograph by K. H.Schrader, “Foundations and Formulations of Cosmetics [Grundlagen und Rezepturen der Kosmetika]”, 2nd Edition, pp. 784-799 (1989). There is therefore a need for new developer substances, which fulfill the above-described requirements to a special extent.
SUMMARY OF THE INVENTION
It is therefore an object of the present invention to provide improved developer compounds for use in a method of dyeing keratin fibers, especially human hair.
It is also an object of the present invention to provide new substituted 2-aminoalkyl-1,4-diaminobenzene compounds for use as developer substances in oxidation dye precursor compositions.
It has now been found surprisingly that certain substituted 2-aminoalkyl-1,4-diaminobenzene compounds of the general formula (I) fulfill the special requirements for developer substances to an especially great extent. When these developer substances are used together with most known coupler substances especially intense colors are produced, which are extraordinarily light-fast and wash-fast.
The new substituted 2-aminoalkyl-1,4-diaminobenzene compounds of the formula (I) according to the invention are:
wherein
R1, R2, R3 and R4, independently of each other, are each hydrogen, a C
1
- to C
6
-alkyl group, a C
1
- to C
4
-hydroxyalkyl group, a C
2
- to C
4
-dihydroxyalkyl group or a C
1
- to C
4
-alkoxy-(C
1
- to C
2
)alkyl group, or R1 and R2 or R3 and R4 together with the nitrogen atom form a four member to eight member aliphatic ring, and wherein at least two of the R1, R2, R3 and R4 substituent groups represent hydrogen;
R5 represents hydrogen, a halogen atom, a C
1
- to C
4
-alkyl group, a C
1
- to C
4
-hydroxyalkyl group or a C
1
- to C
4
-alkoxy group;
R6 and R7, independently of each other, each represent hydrogen, a C
1
- to C
2
-alkoxy group, a C
1
- to C
6
-alkyl group, a C
1
- to C
6
-alkenyl group, a C
1
- to C
4
-hydroxyalkyl group, a C
3
- to C
4
-dihydroxyalkyl group, a C
1
- to C
4
-aminoalkyl group, a C
1
- to C
4
-dimethylaminoalkyl group, a C
1
- to C
4
-acetylaminoalkyl group, a C
1
- to C
4
-methoxyalkyl group, a C
1
- to C
4
-ethoxyalkyl group, a C
1
- to C
4
-cyanoalkyl group, a C
1
- to C
4
-carboxyalkyl group, a C
1
- to C
4
-aminocarbonylalkyl group, a pyridylmethyl group, a furfuryl group, a hydrogenated furfuryl group, a substituted pyridyl group, a group of the formula II:
a group of the formula III:
a group of the formula IV:
wherein at least one of the R6 and R7 groups is not hydrogen, or R6 and R7 together with the nitrogen atom form one of the following rings:
R8 represents hydrogen or a C
1
- to C
6
-alkyl group;
R9 represents hydrogen, a carboxy group or an aminocarbonyl group;
R10 and R 11, independently of each other, each represent hydrogen, a hydroxy group, an aminocarbonyl group, a methylthiomethyl group, a substituted phenyl group having a phenyl group substituent or a hydroxy group substitutent or a group of the formula:
R12, R13, R14, R15 and R16 are each, independently of each other, hydrogen, a halogen atom, a cyano group, a hydroxy group, a C
1
- to C
4
-alkoxy group, a C
1
- to C
4
-hydroxyalkoxy group, a C
1
- to C
6
-alkyl group, a C
1
- to C
4
-alkylthioether group, a mercapto group, a nitro group, an amino group, an alkylamino group, a hydroxyalkylamino group, a dialkylamino group, a di(hydroxyalkyl)amino group, a (dihydroxyalkyl)amino group, a (hydroxyalkyl)alkylamino group, a trifluoromethane group, a —C(O)H group, a —C(O)CH
3
group, a —C(O)CF
3
group, a —Si(CH
3
)
3
group, a C
1
- to C
4
-hydroxyalkyl group, a C
3
- to C
4
-dihydoxyalkyl group, or two of the groups R12 to R16 next to each other form an —O—CH
2
—O— bridge;
R17 represents a C
1
- to C
4
-alkyl group or a a C
1
- to C
4
-hydroxyalkyl group; R18 represents hydrogen or a C
1
- to C
6
-alkyl group;
R19 represents one or more hydrogen, or hydroxy-, carboxy-, aminocarbonyl-, or hydroxymethyl group; and
R20 represents hydrogen or a C
1
- to C
6
-alkyl group, with the proviso that R
1
, R2 and R8 are not each hydrogen when (i) R3 and R4 are a C
1
- to C
4
-alkyl group or
R3 and R4 together with the nitrogen atom form a morpholino-, pyrrolidino-, piperidino- or hexamethylenimino ring, and when (ii) R5 is in the 5-position of the aromatic ring and R5 is hydrogen, a C
1
- to C
4
-alkyl group or a halogen atom, and
when (iii) R6 and R7, independently of each other, are a C
1
- to C
4
-alkyl group or a phenyl group or R3 and R4 taken together with the nitrogen atom form an unsubstituted piperidino- or pyrrolidino- ring;
or a physiologically compatible, water-soluble salt thereof.
The following are examples of the compounds of formula (I):
2-(2,3-dihydroxypropyl)aminomethyl-1,4-diaminobenzene; 2-ethylaminomethyl-1,4-diaminobenzene; 2-(isopropylaminomethyl)-1,4-diaminobenzene; 2-propylaminomethyl-1,4-diaminobenzene; 2-pyrrolidin-1-yl-methyl-1,4-diaminobenzene; 2-[(2-methoxyethylamino)methyl]-1,4-diaminobenzene; 2-morpholin-4-yl-methyl-1,4-diaminobenzene; 2-(2,5-diaminobenzylamino)-butan-1-ol; 2-{[(furan-2-ylmethyl)amino]methyl)-1,4-diaminobenzene; N-(2,5-diaminobenzyl)-O,N-dimethylhydroxylamine; 2-(4-methylpiperazin-1-yl-methyl)-1,4-diaminobenzene; 1-(2,5-diaminobenzyl)piperidin-4-ol; N-[2-(2,5-diaminobenzylamino)ethyl]acetamide; 2-[(2-morpholin-4-yl-ethylamino)methyl]-1,4-diaminobenzene; 2-allylaminomethyl-1,4-diaminobenzene; 2-(2,5-diaminobenzylamino)propan-1-ol; 2-[(3-imidazol-1-yl-propylamino)-methyl]-1,4-diaminobenzene; 2-{[(tetrahydrofuran-2-yl-methyl)amino]methyl}-1,4-diaminobenzene; 4-(2,5-diaminobenzylamino)aniline; 3-(2,5-diaminobenzylamino)phenol; 5-(2,5-diaminobenzylamino)-2-methylphenol; 2-[(2-dimethylaminoethylamino)-methyl]-1,4-diaminobenzene; 4-(2,5-diaminobenzylamino)butan-1-ol; 2-[(3-ethoxypropylamino)methyl]-1,4-diaminobenzene; 2-[(3-methoxy-phenylamino)-methyl]-1,4-diaminobenzene; 2-[(4-chlorophenylamino)methyl]-1,4-diaminobenzene; 2-[(cyclopropyl-methylamino)methyl]-1,4-diaminobenzene; 2-(2,5-diaminobenzylamino)-4-nitrophenol; 2-[(4-chlorobenzylamino)methyl]-1,4-diaminobenzene; 2-[(2,5-diaminobenzyl)methylamino]-

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