p-Aminophenol derivative compounds and dye compositions...

Details p-Aminophenol derivative compounds and dye compositions... p-Aminophenol derivative compounds and dye compositions...

2001-04-27

2003-07-15

Kopec, Mark (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S405000, C008S409000, C008S412000, C008S421000, C008S423000, C548S400000, C549S200000, C549S001000

Reexamination Certificate

active

06592631

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to new p-aminophenol derivative compounds with substituents in the 2-position and compositions for dyeing keratin fibers, especially human hair, containing these new compounds.
2. Prior Art
Oxidation dye compounds have long attained substantial importance in the art of dyeing keratin fibers, especially hair dyeing. The dyeing caused by those compounds occurs by reaction of certain developer substances with certain coupler substances in the presence of a suitable oxidizing agent. For example, 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol and 1,4-diaminobenzene can be used as developer substances, while resorcinol, 4-chlororesorcinol, 1-naphthol, 3-aminophenol and derivatives of m-phenylen-diamine can be mentioned as coupler substances. There are numerous additional requirements for oxidation dye compounds that are used to dye human hair besides color in the desired intensity. Thus the dye compounds must be unobjectionable in regard to toxicological and dermatological properties and must provide the desired hair color with a good light fastness, fastness to a permanent wave treatment, acid fastness and fastness to rubbing. The color of the hair dyed with the dye compounds in each case must be stable for at least 4 to 6 weeks to light, rubbing and chemical agents. Furthermore an additional requirement is the production of a broad palette of different color shades using different developer and coupler substances. To obtain natural and especially fashionable color shades in the red region p-aminophenol is used, alone or in a mixture with another developer substance, in combination with a suitable coupler substance. Introduction of substituents on the p-aminophenol to improve its properties has already been attempted. DE-OS 196 07 751 discloses dye compositions, which contain p-aminophenol compounds with substituents in the 2-position acting as developer substances.
It is not possible to fulfill all the above-mentioned requirements with the currently known dye compounds. There is thus a need for new developer substances that fulfill the above-mentioned requirements in special ways.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide improved developer compounds that fulfill the above-described requirements in a special manner.
It has now been surprisingly found that the new p-aminophenol derivative compounds according to formula (I) fulfill the many requirements for developer compounds to an especially great extent. Particularly bright or intense color shades are produced using these developer substances with predominantly known coupler substances, which are however extraordinarily light fast and fast to washing.
The subject matter of the present invention thus includes p-aminophenol derivative compounds of formula (I), or their physiologically compatible water-soluble salts,
wherein
X is oxygen, sulfur or NR5,
R1 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;
R2 and R4, independently of each other, each represent hydrogen, a hydroxy group, a halogen atom, a cyano group, a C
1
- to C
4
-alkoxy 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, a C
1
- to C
6
-alkylamino group, a (C
1
- to C
6
)-dialkylamino 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
-dihydroxyalkyl group, a —CH═CHR6 group, a —(CH
2
)
p
-CO
2
R7 group or a —(CH
2
)
p
-R8 group, with p=1, 2, 3 or 4 a —C(R9)═NR10 group or a C(R11)H—NR12R13 group;
R3 represents hydrogen, a halogen atom, a C
1
- to C
6
-alkyl group, or a —C(O)H group;
R5 represents hydrogen, a C
1
- to C
6
-alkyl group, a C
1
- to C
4
-hydroxyalkyl group, a phenyl group or an acetyl group;
R6 represents hydrogen, a hydroxy group, a nitro group, an amino group, a —CO
2
R7 group or a —C(O)CH
3
group;
R7, R9 and R11 each represent, independently of each other, hydrogen or a C
1
- to C
4
-alkyl group;
R8 represents an amino group or a nitrile group;
R10, R12 and R13 each represent, independently of each other, hydrogen, a hydroxy group, a C
1
- to C
4
-alkyl group, a C
1
- to C
4
-hydroxyalkyl group, a C
3
- to C
4
-dihydroxyalkyl group or a group of formula (II):
and R14 represents hydrogen, an amino group or a hydroxy group.
The compounds of formula (I) include especially: 4-amino-2-(2-thienyl)-phenol; 4-amino-2-(2-furyl)-phenol; 4-amino-2-(pyrrol-2-yl)-phenol; 4-amino-2-(1-methyl-1H-pyrrol-2-yl)phenol; 4-amino-3-chloro-2-(2-thienyl)-phenol; 4-amino-3-methyl-2-(2-thienyl)-phenol; 4-amino-5-chloro-2-(2-thienyl)phenol; 4-amino-5-methyl-2-(2-thienyl)phenol; 4-amino-6-chloro-2-(2-thienyl)-phenol; 4-amino-6-methyl-2-(2-thienyl)-phenol; 4-amino-2-(3-acetyl-2-thienyl)-phenol; 4-amino-2-(3-chloro-2-thienyl)-phenol; 4-amino-2-(3-formyl-2-thienyl)-phenol; 4-amino-2-(3-methyl-2-thienyl)-phenol; 4-amino-2-(3-nitro-2-thienyl)phenol; 4-amino-2-(4-acetyl-2-thienyl)-phenol; 4-amino-2-(4-chloro-2-thienyl)phenol; 4-amino-2-(4-formyl-2-thienyl)-phenol; 4-amino-2-(4-methyl-2-thienyl)phenol; 4-amino-2-(4-nitro-2-thienyl)phenol; 4-amino-2-(5-acetyl-2-thienyl)-phenol; 4-amino-2-(5-chloro-2-thienyl)-phenol; 4-amino-2-(5-formyl-2-thienyl)phenol; 4-amino-2-(5-methyl-2-thienyl)-phenol; 4-amino-2-(5-nitro-2-thienyl)phenol as well as physiologically compatible salts of these compounds.
Preferred compounds of formula (I) include those in which (i) R1 represents hydrogen and/or (ii) at least one of the groups R2, R3 and R4 represents hydrogen or a methyl group and/or (iii) X represents sulfur or oxygen.
The particularly preferred p-aminophenol derivative compounds of formula (I) include 4-amino-2-(2-thienyl)phenol; 4-amino-2-(3-methyl-2-thienyl) phenol and 4-amino-2-(5-methyl-2-thienyl) phenol and its physiologically compatible derivative compounds.
The compounds of formula (I) can be employed both as free bases and also in the form of their physiologically compatible salts with inorganic or organic acids, such as hydrochloroic acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, lactic acid or citric acid.
The preparation of aminophenol derivative compounds of formula (I) can occur using the known literature synthesis methods. For example, it can occur by a palladium (0) catalyzed coupling of a substituted benzene of formula (II):
with a heterocyclic compound of the formula (III):
subsequently splitting off the protective group and, if necessary, reducing the nitro group; wherein the groups in formula (II) and (III) have the following significance: Ra represents a protective group, for example as described in the chapter “Protective Groups” in Organic Synthesis, Chapter 7, Wiley Interscience, 1991 and Rb represents NHRa group or a nitrogroup; one of the groups Rc and Rd represent a halogen group, while the other represents a B(OH) group, and X, R1, R2, R3 and R4 have the same significance as in formula (I).
The compounds of formula (I) are especially suitable as developer substances in oxidation dye compositions and permit a broad palette of various color shades, which extend from blonds to browns, purples, violets to blue and black shades.
Oxidation dye compositions for oxidative dyeing of keratin fibers, for example hair, fur, feathers or wool, especially human hair, based on a combination of developer and coupler substances, which contain at least one p-aminophenol derivative compound of formula (I) as developer substance, are also part of the subject matter of the present invention.
The aminophenol derivative compounds of formula (I) are present in the oxidation dye compositions according to the invention in an amount of about 0.005 to 20 percent by weight, however an amount of from about 0.01 to 5.0 percent by weight is preferred and an amount of from 0.1 to 2.5 percent by weight is particularly preferred.
The following coupler compounds are preferred in the composition

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