Structure-improving hair care agents

Details Structure-improving hair care agents Structure-improving hair care agents

2002-12-06

2004-09-07

Venkat, Jyothsna (Department: 1615)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

C424S070200, C514S277000, C514S257000

Reexamination Certificate

active

06787128

ABSTRACT:

SUMMARY OF THE INVENTION
This invention relates to the use of compounds belonging to the group of vitamin B6 and derivatives thereof for improving the structure and strength of hair keratin and the fastness to washing of hair colors in preparations for topical application.
BACKGROUND OF THE INVENTION
Hair keratin is structurally damaged by regular treatment with alkaline, strongly reducing or oxidizing chemicals, for example in permanent waving, coloring or bleaching of the hair. Such damage is reflected in a weight loss, in a reduction in the melting point of the keratin and in increasing fragility, poor combability and a deterioration in the hold and body of the hair. In addition, structurally damaged hair is often dull and lackluster in appearance.
To overcome this drawback, structure-improving additives, for example formaldehyde and formaldehyde donors, S-acetyl succinanhydride, ammonium vinyl phosphonate, ammonium phosphate, boric acid, oxazolidines, reducing sugars, tocopherols or so-called onic acids (for example gluconic acid), have already been added to hair-care preparations. Although such additives are effective to a certain extent, their effect on seriously damaged hair is still unsatisfactory. Accordingly, there was still a need to find structure-improving additives for hair which would be suitable for treating the hair after permanent waving or coloring processes.
Pyridoxine (pyridoxol) and other compounds belonging to the vitamin B6 group have already been proposed for use in hair tonics for reducing refatting and for stimulating hair growth.
EP 0678293 A2 proposes topical compositions containing pyridoxine tripropionate for treating the hair and skin. EP 001079 A1 describes describes anti-seborrheic cosmetic compositions containing pyridoxine tripalmitate as their active ingredient.
DESCRIPTION OF THE INVENTION
The present invention relates to the use of vitamin B6 derivatives corresponding to formula (I):
in which
A and B independently of one another represent hydrogen, halogen, a C
1-4
alkyl group, a C
3-6
cycloalkyl group, a C
1-4
monohydroxyalkyl group, a C
2-4
oligohydroxyalkyl group, a C
1-4
aminoalkyl group, a group —OR or a group —NR
1
R
2
, where R
1
and R
2
independently of one another represent hydrogen, a C
1-4
alkyl group or a C
1-4
monohydroxyalkyl group or R
1
and R
2
together with the nitrogen atom form a saturated ring,
C represents a group —OR, —NR
1
R
2
, —OP(O)(OR
3
)
2
, a C
1-4
monohydroxyalkyl group, a C
2-4
oligohydroxyalkyl group or a C
1-4
alkyl group,
D represents a group —OR, a carboxy group, a C
1-22
alkoxycarbonyl group, a formyl group, a group —CH
2
OR or a group —CH
2
—NR
2
,
E represents a group —OR, —OP(O)(OR
3
)
2
, a C
1-4
monohydroxyalkyl group or a C
2-4
oligohydroxyalkyl group,
R representing hydrogen, a C
1-4
alkyl group, a C
1-22
acyl group, a hydroxy-C
2-22
-acyl group, a C
2-10
carboxyacyl group, a C
3-10
oligocarboxyacyl group, an oligocarboxymonohydroxy-C
3-10
-acyl group, an oligocarboxyoligohydroxy-C
3-10
-acyl group, a C
3-8
cycloalkyl group, a C
1-4
monohydroxyalkyl group, a C
2-4
oligohydroxyalkyl group, an aryl group which may contain a hydroxy, nitro or amino group, a heteroaromatic group or a group —CH
2
CH
2
NR
1
R
2
, where R
1
and R
2
are as defined above,
R
3
representing hydrogen or a C
1-5
alkyl group,
or one of the corresponding physiologically compatible salts, for improving the structure and strength of hair keratin and the fastness to washing of hair colors by topical application of preparations containing these derivatives/salts.
Compounds corresponding to formula (I) in which one of the two groups A and B is hydrogen are preferred.
Compounds corresponding to formula (I) in which one of the two groups A and B is hydrogen and the other group is a C
1-4
alkyl group are preferred.
Other preferred compounds of formula (I) are those in which C is a hydroxy group, a C
1-4
monohydroxyalkyl group or a C
2-4
oligohydroxyalkyl group.
According to the invention, compounds of formula (I) in which D is a hydroxymethyl group, a hydroxy group, a carboxy group, a group —CH
2
—NR
2
or a formyl group are preferred.
Other preferred compounds of formula (I) are those in which E is a hydroxy group or a group —OP(O)(OH)
2
.
Particularly preferred compounds corresponding to formula I are pyridoxine (A=H, B=CH
3
, C=OH, D=CH
2
OH, E=OH), pyridoxal (A=H, B=CH
3
, C=OH, D=CHO, E=OH), pyridoxal-5′-phosphate (A=H, B=CH
3
, C=OH, D=CHO, E=OP(O)(OH)
2
) and pyridoxamine (A=H, B=CH
3
, C=OH, D=CH
2
NH
2
, E=OH).
Examples of C
1-4
alkyl groups in the compounds according to the invention are methyl, ethyl, n-propyl, isopropyl, n-butyl and tert butyl. Preferred alkyl groups are methyl and ethyl. Methyl is a particularly preferred alkyl group. Preferred C
3-6
cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Cyclohexyl and cyclopentyl are particularly preferred groups. Preferred C
1-4
monohydroxyalkyl groups are the groups hydroxymethyl, 2-hydroxyethyl, 3-hydroxypropyl or 4-hydroxybutyl; hydroxymethyl and 2-hydroxyethyl are particularly preferred monohydroxyalkyl groups. A preferred C
24
oligohydroxyalkyl group is the 1,2-dihydroxyethyl group. Preferred C
1-22
acyl groups are, for example, acetyl, propionyl, butyryl, valeryl, capryl, lauryl, myristyl, palmityl, stearyl, linolyl, behenyl. Examples of a hydroxy-C
2-22
-acyl group are salicylic acid or lactic acid. Preferred C
2-10
carboxyacyl groups are derived, for example, from malonic acid, succinic acid or adipic acid. One example of a preferred C
3-10
oligocarboxyacyl group is glyceric acid. A preferred oligocarboxymonohydroxy-C
3-10
-acyl group is derived, for example, from citric acid or malic acid. Preferred oligocarboxyoligohydroxy-C
3-10
-acyl groups are derived, for example, from tartaric acid. According to the invention, preferred halogen substituents are fluorine, chlorine, bromine and iodine; chlorine and bromine are particularly preferred. Physiologically compatible salts in the context of the invention are salts of inorganic or organic acids, for example hydrochlorides, sulfates or hydrobromides. According to the invention, the other terms used are derived from the definitions given here.
The ester derivatives of the compounds corresponding to formula (I) also have physiological and hair-structure-improving properties. This applies in particular to the esters of pyridoxine which can be converted by hydrolysis into pyridoxine. In addition, the ester derivatives acquire improved lipid solubility compared with the non-esterified derivatives. Other examples of carboxylic acid ester derivatives of pyridoxine are derived from the carboxylic acids, such as formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, pivalic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, glyceric acid, glyoxylic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, propiolic acid, crotonic acid, isocrotonic acid, elaidic acid, maleic acid, fumaric acid, muconic acid, citraconic acid, mesaconic acid, camphor acid, benzoic acid, o,m,p-phthalic acid, naphthoic acid, toluylic acid, hydratropic acid, atropic acid, cinnamic acid, isonicotinic acid, nicotinic acid, bicarbamic acid, 4,4′-dicyano-6,6′-binicotinic acid, 8-carbamoyloctanoic acid, 1,2,4-pentanetricarboxylic acid, 2-pyrrole carboxylic acid, 1,2,4,6,7-naphthalene pentaacetic acid, malonaldehydic acid, 4-hydroxyphthalamidic acid, 1-pyrazole carboxylic acid, gallic acid or propane tricarboxylic acid, and from dicarboxylic acids selected from the group consisting of compounds corresponding to general formula (II):
in which Z represents a linear or branched alkyl or alkenyl group containing 4 to 12 carbon atoms, n is a number of 4 to 12 and one of the two groups X and Y represents a COOH group and the other represents hydrogen or a methyl or ethyl

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