U.S. patent application number 12/302252 was filed with the patent office on 2010-02-04 for process for straightening keratin fibres with a heating means and denaturing agents.
Invention is credited to Philippe Barbarat, Gerard Malle, Michel Philippe.
Application Number | 20100028280 12/302252 |
Document ID | / |
Family ID | 37672328 |
Filed Date | 2010-02-04 |
United States Patent
Application |
20100028280 |
Kind Code |
A1 |
Philippe; Michel ; et
al. |
February 4, 2010 |
PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND
DENATURING AGENTS
Abstract
The invention relates to a process for straightening keratin
fibres, comprising: (i) a step in which a straightening composition
containing at least two denaturing agents is applied to the keratin
fibres, (ii) a step in which the temperature of the keratin fibres
is raised, using a heating means, to a temperature of between 110
and 250.degree. C.
Inventors: |
Philippe; Michel; (Wissous,
FR) ; Malle; Gerard; (Villiers S/Morin, FR) ;
Barbarat; Philippe; (Bois-Colombes, FR) |
Correspondence
Address: |
FINNEGAN, HENDERSON, FARABOW, GARRETT & DUNNER;LLP
901 NEW YORK AVENUE, NW
WASHINGTON
DC
20001-4413
US
|
Family ID: |
37672328 |
Appl. No.: |
12/302252 |
Filed: |
May 23, 2007 |
PCT Filed: |
May 23, 2007 |
PCT NO: |
PCT/FR2007/000870 |
371 Date: |
May 18, 2009 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
60814529 |
Jun 19, 2006 |
|
|
|
Current U.S.
Class: |
424/70.2 |
Current CPC
Class: |
A61K 8/43 20130101; A61Q
5/04 20130101; A61K 8/42 20130101; A61K 8/365 20130101; A45D 7/06
20130101; A61K 2800/24 20130101 |
Class at
Publication: |
424/70.2 |
International
Class: |
A61K 8/40 20060101
A61K008/40; A61Q 5/04 20060101 A61Q005/04 |
Foreign Application Data
Date |
Code |
Application Number |
May 24, 2006 |
FR |
0651911 |
Claims
1. Process for relaxing keratin fibres, comprising: (i) applying to
the keratin fibres a hair-relaxing composition containing at least
two denaturing agents, (ii) raising the temperature of the keratin
fibres, using a heating means, to a temperature of between 110 and
250.degree. C.
2. Process according to claim 1, wherein the pH of the composition
is less than 7.
3. Process according to claim 1, wherein the hair-relaxing
composition comprises an overall concentration of between 2 M and 8
M of the said denaturing agents.
4. Process according to claim 1, wherein the temperature is raised
to a temperature of between 140.degree. C. and 220.degree. C.
5. Process according to claim 1, wherein the molar mass of the
denaturing agents is between 40 and 600 g/mol.
6. (canceled)
7. (canceled)
8. Process according to claim 1, wherein the denaturing agents are
chosen from ureas, guanidines, .alpha.-hydroxy acid and
.alpha.-keto acid derivatives, mono-, di-, tri- or polyhydroxylated
aromatic derivatives, cyclic or linear amides, surfactants or
detergents, amidines, thioureas, urethanes, alcohols, polyols,
amine oxides, metal salts, sulfamides, carboxylic acids, amino
acids, and nitrogenous heterocycles of the imidazole or triazole
family.
9. Process according to claim 1, wherein at least one of the
denaturing agents is a urea.
10. Process according to claim 9, wherein the urea corresponds to
formula (I): ##STR00014## in which: R1, R2, R3 and R4 represent,
independently: (v) a hydrogen atom or (vi) a linear or branched
C1-C4 lower alkyl or alkenyl radical, optionally substituted with a
radical chosen from: hydroxyl, amino, dimethylamino, carboxyl or
carboxamide or N-methylcarboxamide, when R1, R2 and R3 represent a
hydrogen atom, R4 may also denote a radical chosen from:
carboxamide; methoxy; ethoxy; 1,2,4-triazolyl; cyclopentyl;
methoxycarbonyl; ethoxycarbonyl; CO--CH.dbd.CH--COOH; phenyl
optionally substituted with a chlorine atom or a hydroxyl radical;
benzyl; or 2,5-dioxo-4-imidazolidinyl, when R1 and R3 represent a
hydrogen atom, R2 may also represent a hydrogen atom or a methyl or
ethyl radical and R4 an acetyl radical, when R1=R2=H, R3 and R4 may
also form, with the nitrogen atom that bears them, a piperidine or
3-methylpyrazole or 3,5-dimethylpyrazole or maleimide ring, R1 and
R2 and also R3 and R4 may also form, with the nitrogen atom that
bears them, an imidazole ring.
11.-13. (canceled)
14. Process according to claim 1, wherein at least one of the
denaturing agents is a guanidine of general formula (III) below:
##STR00015## in which: R1, R2, R3, R4 and R5 represent,
independently: (vii) a hydrogen atom or (viii) a linear or branched
C1-C4 lower alkyl or alkenyl radical, optionally substituted with
one or two radicals chosen from: hydroxyl, amino, dimethylamino,
methoxy, ethoxy, carboxyl, carboxamide, N-methylcarboxamide or
SO.sub.3H, when R1, R2 and R3 and R4 represent a hydrogen atom, R5
may also denote a radical chosen from the following: acetyl;
chloroacetyl; carboxamide; methoxy; ethoxy; 1,2,4-triazolyl;
cyclopentyl; methoxycarbonyl; ethoxycarbonyl; CO--CH.dbd.CH--COOH;
phenyl optionally substituted with a chlorine atom or a hydroxyl
radical; benzyl; thiazolidone; benzimidazole; benzoxazole;
benzothiazole; or C(.dbd.NH)--NR6R7 in which R6 and R7 denote,
independently of each other, a hydrogen atom or a linear or
branched C1-C4 lower alkyl radical, optionally substituted with one
or two radicals chosen from: hydroxyl, amino, dimethylamino,
carboxyl or carboxamide; or N-methylcarboxamide; or alternatively a
phenyl radical, when R1=R2=R3=H, R4 and R5 may also form, with the
nitrogen atom that bears them, a pyrrolidine, piperidine, pyrazole
or 1,2,4-triazole ring optionally substituted with one or two
radicals chosen from: hydroxyl, amino or carboxyl, when R1=R2=H and
R4=H or methyl, R3 and R5 may also together form a 5-membered ring
optionally containing an oxo group, and the organic or mineral
salts thereof.
15.-18. (canceled)
19. Process according to claim 1, wherein at least one of the
denaturing agents is a .alpha.-keto acid derivative of general
formula (V): ##STR00016## R5 represents COOH, a linear or branched
C1-C6 alkyl optionally substituted with an OH, COOH or Br radical;
a phenyl or benzyl optionally substituted with an OH or COOH
radical; or alternatively an indolyl radical or ##STR00017## and
the stereoisomers, organic or mineral salts and solvates
thereof.
20.-33. (canceled)
Description
[0001] The invention relates to a process for relaxing keratin
fibres with a heating means and at least two denaturing agents.
[0002] The relaxing process according to the invention is performed
without using a reducing agent or a lanthionization agent. It does
not comprise any reducing or lanthionizing step.
[0003] According to the invention, the term "keratin fibres" means
fibres of human or animal origin such as head hair, bodily hair,
the eyelashes, wool, angora, cashmere or fur. Although the
invention is not limited to particular keratin fibres, reference
will nevertheless be made more particularly to head hair.
[0004] According to the invention, the term "relaxing" covers the
relaxing, straightening or uncurling of Caucasian or African
hair.
[0005] The term "denaturing agent" means a compound of organic or
mineral origin containing both at least one electron-donating site
of basic or nucleophilic nature and at least one electron-accepting
site of acidic or electrophilic nature, which interacts with the
weak bonds of keratin.
[0006] According to the invention, a denaturing agent is a compound
capable of reducing the optical rotation of a model protein, for
instance bovine serum albumin, by at least 7.degree. and/or
5.degree. at 579 nm, the measurements being taken after incubation
for 3 hours at 37.degree. C., using a polarimeter, as described in
Biochemistry 2 (1), 47-57, 1963: [0007] either in TRIS 0.05 M pH
7.6 buffer [0008] or in a 5.45 M urea solution when the solubility
of the compound is insufficient in the TRIS 0.05 M pH 7.6
buffer.
[0009] The compound is considered as being a denaturing agent
according to the invention if the reduction of the optical rotation
is at least 70 in TRIS 0.05 M pH 7.6 buffer and/or at least 50 in
5.45 M urea solution.
[0010] The term "weak bonds of keratin" means all the non-covalent
bonds such as: [0011] the saline bonds resulting from coulombic
interactions between the functional groups present on the side
chains of amino acids [0012] the hydrogen bonds that become
established between amino acids especially via oxygen and hydrogen
atoms [0013] the hydrophobic bonds resulting from the tendency of
the non-polar chains of amino acids to associate in order to
minimize the contacts with water.
[0014] The term "heating means" means any means for heating keratin
fibres to a temperature of at least 110.degree. C., such as heating
irons, for example flat or round irons, microwave generators or
sources of infrared radiation.
[0015] Two techniques are used for permanently reshaping the hair.
They are based on cleavage of the disulfide covalent bonds present
in keratin (cystine): [0016] the first consists, in a first stage,
in performing this opening of the disulfide bonds using a
composition containing a reducing agent, and then, after having
preferably rinsed the hair, in reconstituting the said disulfide
bonds in a second stage, by applying to the hair, which has been
placed under tension beforehand with rollers or the like or shaped
or straightened out by other means, an oxidizing composition also
known as a fixer, so as to give the head of hair the desired shape.
This technique makes it possible either to make the hair wavy or to
relax it, uncurl it or straighten it out; [0017] the second
consists in performing a "lanthionization" operation using a
composition containing a base belonging to the hydroxide family.
This leads to replacement of the disulfide bonds (--CH2-S--S--CH2-)
with lanthionine bonds (--CH2-S--CH2-). This lanthionization
operation involves two consecutive chemical reactions: [0018] the
first reaction consists of a beta-elimination on cystine brought
about by a hydroxide ion, leading to the cleavage of this bond and
to the formation of dehydroalanine:
[0018] ##STR00001## [0019] the second reaction is a reaction of
dehydroalanine with a thiol group. Specifically, the double bond of
the dehydroalanine formed is a reactive double bond. It can react
with the thiol group of the cysteine residue that has been released
to form a new bond referred as a lanthionine bridge or bond or
residue.
##STR00002##
[0020] Relative to the first technique using a reducing agent, this
lanthionization technique does not require a fixing step, since the
formation of the lanthionine bridges is irreversible. It is thus
performed in a single step and makes it possible either to make the
hair wavy, or to relax it, uncurl or straighten it out. However, it
is mainly used for relaxing naturally curly hair.
[0021] For the first technique, the reducing compositions generally
used for the first step of a permanent-waving or hair-relaxing
operation contain thiols, sulfites or bisulfites as reducing agent.
These agents are generally used in essentially aqueous medium at
concentrations of between 0.5 and 1 M to obtain good opening of the
disulfide bonds. Among the thiols, those commonly used are
thioglycolic acid, cysteamine, glyceryl monothioglycolate,
thiolactic acid and cysteine. Thioglycolic acid is particularly
efficient at reducing the disulfide bonds of keratin at alkaline
pH, especially in the form of ammonium thioglycolate, and
constitutes the product most frequently used in permanent waving
("hair waving"). It has been found, however, that thioglycolic acid
must be used in sufficiently basic medium (in practice at a pH of
between 8.5 and 9.5) if curling of satisfactory intensity is to be
obtained. Besides the drawback of releasing an unpleasant odour
requiring the use of more or less efficient fragrances to mask the
odours, the use of a thiol at alkaline pH also results in
degradation of the fibre and most particularly in impairment of
artificial colorations.
[0022] Sulfites or bisulfites are mainly used for relaxing the
hair. They have drawbacks similar to those of thiols, with lower
efficacy.
[0023] Thiols and sulfites (or bisulfites) also have the drawback
of having poor stability in aqueous solution.
[0024] In general, the durability of the reshaping effects obtained
with thiols and sulfites by reduction of disulfides following by
fixing is judged to be very much lower than that which may be
obtained via the lanthionization technique.
[0025] For the second technique, the compositions generally used to
perform lanthionization contain as base a hydroxide such as sodium
hydroxide, guanidinium hydroxide or lithium hydroxide. These
lanthionization active agents, which allow opening of the disulfide
bonds via a beta-elimination mechanism, are generally used as a
water-oil emulsion at concentrations of between 0.4 and 0.6 M, by
leaving them to act generally for 10 to 15 minutes at room
temperature. Sodium hydroxide remains the agent most frequently
used. Guanidinium hydroxide is now the preferred compound for many
compositions. These two hydroxides, sodium hydroxide and
guanidinium hydroxide, are the two main agents used for the
relaxing or uncurling of naturally curly hair. They have several
advantages over ammonium thioglycolate and sulfites, in particular
the absence of unpleasant odour, the fact that only one operating
step is required (shorter treatment time) and much greater
durability and efficacy of reshaping of the hair.
[0026] However, these hydroxides have the major drawback of being
caustic. This causticity affects the scalp by causing irritation,
which is occasionally severe. This may be partially remedied by
applying beforehand to the scalp fatty protective cream often
referred to as a "base" or "base cream", the word "base" in this
case not having the meaning of a basic agent in the chemical sense.
When the protective cream is combined with the hydroxide in a
single composition, it is generally referred to as "no-base", as
opposed to the above name. This "no-base" technique is
preferred.
[0027] The causticity of hydroxides also affects the state of the
hair by firstly giving it a coarse feel and secondly making it much
more brittle, this brittleness possibly going as far as crumbling
or breaking or even dissolution of the hair if the treatment is
prolonged. In certain cases, hydroxides also cause decoloration of
the natural colour of the hair.
[0028] Formulations containing sodium hydroxide are generally
referred to as "lye relaxers" and those not containing it are
referred as "no-lye relaxers".
[0029] The main relaxing formulations known as "no-lye" relaxers
use guanidinium hydroxide. Since guanidinium hydroxide is unstable,
it is generated at the time of use by mixing guanidinium carbonate
and a source of sparingly soluble hydroxide such as calcium
hydroxide. The reaction between these two compounds leads to the
formation of guanidinium hydroxide and calcium carbonate, which
precipitates in the composition. The presence of this precipitate
makes the final rinsing of the hair much more difficult and leaves
mineral particles on the hair and the scalp, which give it a coarse
feel and an unaesthetic appearance resembling dandruff. The recent
success of guanidinium hydroxide ("no-lye") over sodium hydroxide
("lye") appears to arise from better relaxing efficacy and better
skin tolerance. However, these techniques using bases of the
hydroxide family remain very aggressive to the hair and the scalp
and require very strict control of the duration of application to
avoid excessive irritation and impairment of the hair that may go
as far as breakage. This aggressiveness arising from the causticity
of hydroxides is justification for not using these hair
lanthionization compositions for permanent waving (hair waving),
but solely for hair straightening or hair relaxing.
[0030] Furthermore, hydroxides are known to be good agents for
hydrolysing amide functions (cf. for example March's Advanced
Organic Chemistry, 5th edition, Wiley Interscience, New York,
"Hydrolysis of Amides" page 474 et seq.), which thus lead to
cleavage of peptide bonds by direct nucleophilic attack. It is thus
probable that the observed impairments of the hair and of keratin
materials in the broad sense are largely due to partial hydrolysis
of the amide bonds of keratin.
[0031] There is thus a real need for relaxing compositions that are
markedly less aggressive to the hair.
[0032] Various studies have been conducted in order to overcome
both the drawbacks of reducing agents (first technique) and/or
those of hydroxides (second technique).
[0033] Thus, many reducing agents have been proposed to replace
thioglycolic acid, but thioglycolic acid in the form of ammonium
thioglycolate remains both the reference compound and the compound
most widely used in cosmetic formulations, not only for shaping but
also for straightening the hair.
[0034] It has also been proposed in numerous patents to combine
common reducing agents (thiols, sulfites or bisulfites) with urea
or alkyl ureas to reduce the irritation and damage caused to the
hair, not only for shaping but also for relaxing. Mention will be
made, for example, of: [0035] patent application CA 1315204, which
describes a composition containing ammonium thioglycolate
(5.5-11.5%) and urea or a monoalkyl urea (1-3%) for shaping the
hair, [0036] patent application U.S. Pat. No. 3,847,165, which
describes a composition containing ammonium thioglycolate (1.2-1.4
M) and urea (2.0-2.7 M) for shaping the hair at an acidic pH,
[0037] patent application NL 6410355, which describes a composition
containing a sulfite (0.8-1.5 M) and urea (0.6-3.0 M) for shaping
and relaxing the hair, [0038] patent application JP 2000/229 819,
which describes a composition containing a sulfite or bisulfite
(0.5-15%), urea (0.5-15%) and an alcohol (ethanol and/or
isopropanol, 1-30%) for shaping and relaxing the hair.
[0039] It has also been proposed in numerous patents to combine
hydroxides, serving as lanthionization active agent, with certain
additives generally serving to protect the hair. Mention will be
made, for example, of: [0040] patent application WO 2002/003 937,
which describes a composition containing C3-C5 monosaccharides,
[0041] patent application WO 2001/064 171, which describes a
composition containing complexing agents, [0042] U.S. Pat. No.
5,641,477, which describes a composition containing a hydrogenated
starch hydrolysate, [0043] patent application WO 02/085 317, which
describes a composition containing organic nucleophiles that react
during the second step with the dehydroalanine formed with
hydroxides, to give new bridges.
[0044] Although all these proposals lead to more or less pronounced
improvements, they are not able to sufficiently reduce the damage
associated with the very causticity of hydroxides.
[0045] As indicated previously, the use of reducing agents leads to
poor durability of the relaxing or straightening of the hair and
the use of hydroxides, on account of their causticity, limits their
use in the field of hair relaxing.
[0046] The use of resorcinol at a concentration of 40% and at a pH
of 7 for relaxing the hair has been reported by M. Wong et al.: M.
Wong, G. Vis-surel, and J. Epps J. Soc. Cosmet. Chem. (1994), 45,
347-352. However, the tests that we have performed under these
conditions on naturally curly African hair do not relax it, but
lead, at the very best, to slight uncurling.
[0047] After considerable studies, it has now been discovered,
entirely surprisingly and unexpectedly, that hair can be durably
relaxed by combining the action of at least two denaturing agents
and of a means of heating to a temperature above 110.degree. C.
Excellent results in terms of relaxing, cosmetic properties of the
hair and fibre integrity are thus obtained.
[0048] Without being bound by theory, the Applicant considers that
there is a combined action, on the keratin fibres, of at least two
denaturing agents and of a heating means, which allows the fibres
to be efficiently and durably relaxed.
[0049] The Applicant has found that it is possible to overcome the
drawbacks of the prior art and to satisfy the abovementioned
objectives by performing a process for relaxing keratin fibres,
comprising: [0050] a step of applying to the keratin fibres a
hair-relaxing composition containing at least two denaturing
agents, [0051] a step of raising the temperature of the keratin
fibres, using a heating means, to a temperature of between 110 and
250.degree. C.
[0052] Advantageously, the denaturing agents have a molar mass of
greater than 18.1 g/mol and preferably between 40 and 600
g/mol.
[0053] Preferably, the hair-relaxing composition comprises an
overall concentration of denaturing agents of between 1 M and 8 M
and more advantageously between 2 M and 8 M of the said denaturing
agents; this corresponds to a weight concentration of between about
6% and about 80% and more advantageously between about 12% and
about 80%, relative to the total weight of the composition, of the
said denaturing agents.
[0054] Advantageously, the temperature is raised using a heating
means to a temperature of between 120.degree. C. and 220.degree. C.
and more advantageously between 140.degree. C. and 220.degree.
C.
[0055] According to one embodiment, the said composition is applied
to wet keratin fibres.
[0056] A step intended to remove the excess composition, for
example using a towel, may also be introduced between the step of
applying the composition and the step of raising the
temperature.
[0057] Preferably, the denaturing agents are chosen from
protein-denaturing agents such as: [0058] ureas, [0059] guanidines,
[0060] .alpha.-hydroxy acid and .alpha.-keto acid derivatives,
mono-, di-, tri- or polyhydroxylated aromatic [0061] derivatives,
[0062] cyclic or linear amides, [0063] surfactants or detergents,
especially those containing sugar or choline or deoxycholine or
polyethylene glycol units, such as the following compounds: [0064]
acetobromo-.alpha.-D-glucose taurodeoxycholic acid sodium salt
[0065] N-octyl-.beta.-D-glucopyranoside [0066] MEGA-8 [0067]
N-hexyl-.beta.-D-glucopyranoside [0068]
N-heptyl-.beta.-D-thioglucopyranoside [0069]
N-heptyl-.beta.-D-glucopyranoside [0070] glycodeoxycholic acid
sodium salt [0071] sodium deoxycholate [0072] sodium cholate [0073]
CHAPSO [0074] CHAPS [0075] octaethylene glycol mono-N-dodecyl ether
[0076] N,N'-bis(3-D-gluconamidopropyl)cholamide [0077]
polyoxyethylene (23) lauryl ether C12E23 [0078] nonaethylene glycol
monododecyl ether [0079] cetrimide [0080] decyl glucoside [0081]
decyl maltoside [0082] N,N-bis(3-D-gluconamidopropyl)deoxycholamide
[0083] digitonine [0084] dodecyl maltoside [0085] dioctyl sodium
sulfosuccinate [0086] lauryldimethylamine oxide [0087] octaethylene
glycol isotridecyl ether [0088] glycocholic acid, sodium salt
[0089] sodium lauryl sulfate [0090] octanoyl-N-methylglucamide
[0091] nonanoyl-N-methylglucamide [0092] decanoyl-N-methylglucamide
[0093] nonyl glucoside [0094] nonaethylene glycol octylphenyl ether
[0095] octyl thioglucoside [0096] polyethylene polypropylene glycol
[0097] monosodium taurocholic acid [0098] nonaethylene glycol
octylphenyl ether [0099] polyoxyethylene sorbitan monolaurate
[0100] polyoxyethylene sorbitan monooleate [0101]
N-octylsulfobetaine [0102] N-decylsulfobetaine [0103]
N-dodecylsulfobetaine [0104] N-hexyldecylsulfobetaine, [0105]
amidines, such as acetamidine hydrochloride, [0106] thioureas,
urethanes, alcohols, polyols, amine oxides such as
N-methylmorpholine N-oxide, metal salts, sulfamides, carboxylic
acids and amino acids, nitrogenous heterocycles of the imidazole or
triazole family, such as imidazole hydrochloride.
[0107] Advantageously, the said denaturing agents are chosen from
the family of ureas, guanidines, .alpha.-hydroxy acid or
.alpha.-keto acid derivatives, mono-, di, tri- or polyhydroxylated
aromatic derivatives, and cyclic or linear amides.
[0108] The term "urea", which may be used as hair-relaxing active
agent, means any derivative comprising in its chemical formula a
carbonyl group simply bonded to two nitrogen atoms. These ureas are
more particularly selected from the compounds of general formulae
(I) and (II) below:
##STR00003##
in which: R1, R2, R3 and R4 represent, independently: [0109] (i) a
hydrogen atom or [0110] (ii) a linear or branched C1-C4 lower alkyl
or alkenyl radical, optionally substituted with a radical chosen
from: hydroxyl, amino, dimethylamino, carboxyl or carboxamide or
N-methylcarboxamide, when R1, R2 and R3 represent a hydrogen atom,
R4 may also denote a radical chosen from: carboxamide; methoxy;
ethoxy; 1,2,4-triazolyl; cyclopentyl; methoxycarbonyl;
ethoxycarbonyl; CO--CH.dbd.CH--COOH; phenyl optionally substituted
with a chlorine atom or a hydroxyl radical; benzyl; or
2,5-dioxo-4-imidazolidinyl, when R1 and R3 represent a hydrogen
atom, R2 may also represent a hydrogen atom or a methyl or ethyl
radical and R4 an acetyl radical, when R1=R2=H, R3 and R4 may also
form, with the nitrogen atom that bears them, a piperidine or
3-methylpyrazole or 3,5-dimethylpyrazole or maleimide ring, and
finally, R1 and R2 and also R3 and R4 may also form, with the
nitrogen atom that bears them, an imidazole ring.
##STR00004##
[0110] in which:
[0111] R5 and R6 represent, independently of each other: [0112] (i)
a hydrogen atom or [0113] (ii) a linear or branched C1-C4 lower
alkyl radical, optionally substituted with a radical chosen from:
hydroxyl, amino, dimethylamino, carboxyl and carboxamide, and
[0114] A represents the radicals: CH2-CH2 or CH.dbd.CH or CH2-CO or
CO--NH or CH.dbd.N or CO--CO or CHOH--CHOH or (HOOC)CH--CH or
CHOH--CO or CH2-CH2-CH2 or CH2-NH--CO or CH.dbd.C(CH3)-CO or
NH--CO--NH or CH2-CH2-CO or CH2-N(CH3)-CH2 or NH--CH2-NH or
CO--CH(CH3)-CH2 or CO--CH2-CO or CO--NH--CO or CO--CH(COOH)--CH2 or
CO--CH.dbd.C(COOH) or CO--CH.dbd.C(CH3) or CO--C(NH2).dbd.CH or
CO--C(CH3).dbd.N or CO--CH.dbd.CH or CO--CH.dbd.N or
CO--N.dbd.CH.
[0115] Among the compounds of formula (I), mention may be made
especially of the following preferred compounds: [0116] urea [0117]
methylurea [0118] ethylurea [0119] propylurea [0120] isopropylurea
[0121] n-butylurea [0122] sec-butylurea [0123] isobutylurea [0124]
tert-butylurea [0125] cyclopentylurea [0126] 1-ethoxyurea [0127]
2-hydroxyethylurea [0128] N-(2-hydroxypropyl)urea [0129]
N-(3-hydroxypropyl)urea [0130] N-(2-dimethylaminopropyl)urea [0131]
N-(3-dimethylaminopropyl)urea [0132] 1-(3-hydroxyphenyl)urea [0133]
benzylurea [0134] N-carbamoylmaleimide [0135] biuret [0136]
N-carbamoylmaleamic acid [0137] 1-piperidinecarboxamide [0138]
1,2,4-triazol-4-ylurea [0139] hydantoic acid [0140] methyl
allophanate [0141] ethyl allophanate [0142] acetylurea [0143]
2-hydroxyethyleneurea [0144] 2-(hydroxyethyl)ethyleneurea [0145]
N-allyl-N'-ethylurea [0146] diallylurea [0147] 2-chloroethylurea
[0148] N,N-dimethylurea [0149] N,N-diethylurea [0150]
N,N-dipropylurea [0151] 1-cyclopentyl-1-methylurea [0152]
1,3-dimethylurea [0153] 1,3-diethylurea [0154]
1,3-bis(2-hydroxethyl)urea [0155] 1,3,bis(2-hydroxypropyl)urea
[0156] 1,3-bis(3-hydroxypropyl)urea [0157] 1,3-dipropylurea [0158]
1-ethyl-3-propylurea [0159] 1-sec-butyl-3-methylylurea [0160]
1-isobutyl-3-methylurea [0161] 1-cyclopentyl-3-methylurea [0162]
N-acetyl-N'-methylurea [0163] trimethylurea [0164]
1-butyl-3,3-dimethylurea [0165] tetramethylurea [0166]
benzylurea.
[0167] Among the compounds of formula (II), mention may be made
especially of the following preferred compounds: [0168] parabanic
acid [0169] 1,2-dihydro-3-H-1,2,4-triazol-2-one [0170] barbituric
acid [0171] uracil [0172] 1-methyluracil [0173] 3-methyluracil
[0174] 5-methyluracil [0175] 1,3-dimethyluracil [0176] 5-azauracil
[0177] 6-azauracil [0178] 5-fluorouracil [0179] 6-fluorouracil
[0180] 1,3-dimethyl-5-fluorouracil [0181] 5-aminouracil [0182]
6-aminouracil [0183] 6-amino-1-methyluracil [0184]
6-amino-1,3-dimethyluracil [0185] 4-chlorouracil [0186]
5-chlorouracil [0187] 5,6-dihydrouracil [0188]
5,6-dihydro-5-methyluracil [0189] 2-imidazolidione hydrate [0190]
1-methyl-2-imidazolidinone [0191] 1,3-dimethyl-2-imidazolidinone
[0192] 4,5-dihydroxyimidazolidin-2-one [0193]
1-(2-hydroxyethyl)-2-imidazolidinone [0194]
1-(2-hydroxypropyl)-2-imidazolidinone [0195]
1-(3-hydroxypropyl)-2-imidazolidinone [0196]
4,5-dihydroxy-1,3-dimethylimidazolidin-2-one [0197]
1,3-bis(2-hydroxyethyl)-2-imidazolidinone [0198]
2-imidazolidone-4-carboxylic acid [0199]
1-(2-aminoethyl)-2-imidazole [0200]
4-methyl-1,2,4-triazoline-3,5-dione [0201]
2,4-dihydroxy-6-methylpyrimidine [0202]
1-amino-4,5-dihydro-1H-tetrazol-5-one [0203] hydantoin [0204]
1-methylhydantoin [0205] 5-methylhydantoin [0206]
5,5-dimethylhydantoin [0207] 5-ethylhydrantoin [0208]
5-n-propylhydantoin [0209] 5-ethyl-5-methylhydantoin [0210]
5-hydroxy-5-methylhydantoin [0211] 5-hydroxymethylhydantoin [0212]
1-allylhydantoin [0213] 1-aminohydantoin [0214] hydantoin 5-acetic
acid [0215] 4-amino-1,2,4-triazolone-3,5-dione [0216]
hexahydro-1,2,4,5-tetrazine-3,6-dione [0217]
5-methyl-1,3,5-triazinon-2-one [0218]
1-methyltetrahydropyrimidin-2-one [0219]
2,4-dioxohexahydro-1,3,5-triazine [0220] urazole [0221]
4-methylurazole [0222] orotic acid [0223] dihydroxyorotic acid
[0224] 2,4,5-trihydroxypyrimidine [0225]
2-hydroxy-4-methylpyrimidine [0226]
4,5-diamino-2,6-dihydroxypyrimidine [0227] barbituric acid [0228]
1,3-dimethylbarbituric acid [0229] cyanuric acid [0230]
1-methylhexahydropyrimidine-2,4-dione [0231]
1,3-dimethyl-3,4,5,6-tetrahydro-2-1H-pyrimidinone [0232]
5-(hydroxymethyl-2,4-(1H,3H)-pyrimidinedione [0233]
2,4-dihydroxypyrimidine-5-carboxylic acid [0234] 6-azathymine
[0235] 5-methyl-1,3,5-triazinan-2-one [0236] N-carbamoylmaleamic
acid [0237] alloxan monohydrate.
[0238] Among the compounds of formula (I), mention may be made
especially of the following particularly preferred compounds:
[0239] urea [0240] methylurea [0241] ethylurea [0242] propylurea
[0243] 1-ethoxyurea [0244] 2-hydroxyethylurea [0245]
N-(2-hydroxypropyl)urea [0246] N-(3-hydroxypropyl)urea [0247]
N-(2-dimethylaminopropyl)urea [0248] N-(3-dimethylaminopropyl)urea
[0249] 1-(3-hydroxyphenyl)urea [0250] N-carbamoylmaleimide [0251]
N-carbamoylmaleamic acid [0252] 1-piperidinecarboxamide [0253]
1,2,4-triazol-4-ylurea [0254] hydantoic acid [0255] acetylurea
[0256] 2-hydroxyethyleneurea [0257] 2-(hydroxyethyl)ethyleneurea
[0258] N-allyl-N'-ethylurea [0259] diallylurea [0260]
2-chloroethylurea [0261] N,N-dimethylurea [0262] 1,3-dimethylurea
[0263] 1,3-diethylurea [0264] 1,3-bis(2-hydroxyethyl)urea [0265]
1,3-dipropylurea [0266] 1-ethyl-3-propylurea [0267]
N-acetyl-N'-methylurea [0268] benzylurea.
[0269] Among the compounds of formula (II) mention made be made
especially of the following particularly preferred compounds:
[0270] 1,2-dihdryo-3-H-1,2,4-traizol-2-one [0271] uracil [0272]
1-methyl-2-imidazolidinone [0273] 1,3-dimethyl-2-imidazolidinone
[0274] 4,5-dihydroxyimidazolidin-2-one [0275]
1-(2-hydroxyethyl)-2-imidazolidinone [0276]
4,5-dihydroxy-1,3-dimethylimidazolidin-2-one [0277]
1,3-bis(2-hydroxyethyl)-2-imidazolidinone [0278]
2-imidazolidone-4-carboxylic acid [0279]
1-(2-aminoethyl)-2-imidazole [0280] hydantoin [0281]
5-hydroxymethylhydantoin [0282] hydantoin 5-acetic acid [0283]
urazole [0284] orotic acid [0285] dihydroxyorotic acid [0286]
2,4,5-trihydroxypyrimidine [0287]
4,5-diamino-2,6-dihydroxypyrimidine [0288]
2,4-dihydroxypyrimidine-5-carboxylic acid [0289]
5-methyl-1,3,5-triazinan-2-one [0290]
1,3-dimethyl-3,4,5,6-tetrahydro-2-1H-pyrimidinone [0291]
N-carbamoylmaleamic acid [0292] alloxan monohydrate.
[0293] The term "guanidine", which may be used as relaxing active
agent, means any derivative comprising in its chemical formula at
least one carbon atom doubly bonded to a nitrogen atom and singly
bonded to two other nitrogen atoms. These guanidines are more
particularly selected from the compounds of general formula (III)
below:
##STR00005##
in which R1, R2, R3, R4 and R5 represent, independently: [0294]
(iii) a hydrogen atom or [0295] (iv) a linear or branched C1-C4
lower alkyl or alkenyl radical, optionally substituted with one or
two radicals chosen from: hydroxyl, amino, dimethylamino, methoxy,
ethoxy, carboxyl, carboxamide, N-methylcarboxamide or SO.sub.3H,
[0296] when R1, R2 and R3 and R4 represent a hydrogen atom, R5 may
also denote a radical chosen from the following: acetyl;
chloroacetyl; carboxamide; methoxy; ethoxy; 1,2,4-triazolyl;
cyclopentyl; methoxycarbonyl; ethoxycarbonyl; CO--CH.dbd.CH--COOH;
phenyl optionally substituted with a chlorine atom or a hydroxyl
radical; benzyl; thiazolidone; benzimidazole; benzoxazole;
benzothiazole; or C(.dbd.NH)--NR6R7 in which R6 and R7 denote,
independently of each other, a hydrogen atom or a linear or
branched C1-C4 lower alkyl radical, optionally substituted with one
or two radicals chosen from: hydroxyl, amino, dimethylamino,
carboxyl or carboxamide; or N-methylcarboxamide; or alternatively a
phenyl radical, [0297] when R1=R2=R3=H, R4 and R5 may also form,
with the nitrogen atom that bears them, a pyrrolidine, piperidine,
pyrazole or 1,2,4-triazole ring optionally substituted with one or
two radicals chosen from: hydroxyl, amino or carboxyl, [0298] when
R1=R2=H and R4=H or methyl, R3 and R5 may also together form a
5-membered ring optionally containing an oxo group, [0299] and the
organic or mineral salts thereof.
[0300] Among the compounds of formula (III), mention may be made
especially of the following preferred compounds: [0301] guanidine
hydrochloride [0302] guanidine acetate [0303] guanidine sulfate
[0304] guanidine carbonate [0305] guanidine bicarbonate [0306]
guanidine phosphate [0307] guanidine sulfamate [0308]
aminoguanidine [0309] aminoguanidine hydrochloride [0310]
aminoguanidine sulfate [0311] aminoguanidine bicarbonate [0312]
1,3-diaminoguanidine hydrochloride [0313] 1-acetylguanidine [0314]
chloroacetylguanidine hydrochloride [0315] guanylurea [0316]
guanylurea phosphate [0317] phenylguanidine carbonate [0318]
phenylguanidine bicarbonate [0319] 1-methylguanidine hydrochloride
[0320] 1,1-dimethylguanidine hydrochloride [0321] 1-ethylguanidine
hydrochloride [0322] 1,1-diethylguanidine hydrochloride [0323]
creatine [0324] creatine monohydrate [0325] creatinine
hydrochloride [0326] agmatine [0327] agmatine sulfate [0328]
guanidinoacetic acid [0329] guanidinosuccinic acid [0330]
3-guanidinopropionic acid [0331] 4-guanidinobutyric acid [0332]
5-guanidinovaleric acid [0333] .beta.-N-methylguanidinopropionic
acid [0334] N-methylguanidinopropionic acid [0335]
N-(2-hydroxyethyl)guanidine [0336] N-(3-hydroxypropyl)guanidine
[0337] biguanide hydrochloride [0338] N-methylbiguanide
hydrochloride [0339] N-ethylbiguanide hydrochloride [0340]
N-propylbiguanide hydrochloride [0341] N-butylbiguanide
hydrochloride [0342] N-butylbiguanide hydrochloride [0343]
1,1-dimethylbiguanide hydrochloride [0344] 1-phenylbiguanide [0345]
1,1,3,3-tetramethylguanidine hydrochloride [0346] 1-phenylbiguanide
[0347] 1,1,3,3-tetramethylguanidine hydrochloride [0348]
2-tert-butyl-1,1,3,3-tetramethylguanidine hydrochloride [0349]
L-arginine [0350] D-arginine [0351] DL-arginine [0352] arginic acid
[0353] N-amidino-N-(2,3-dihydroxypropyl)glycine [0354]
N-amidinotaurine [0355] 2-imino-2-imidazolidineacetic acid [0356]
1-(2,2-diethoxyethyl)guanidine [0357] 1H-pyrazole-1-carboxamidine
hydrochloride [0358]
5-hydroxy-3-methyl-1H-pyrazole-1-carboximidamide [0359]
3,5-diamino-1H-1,2,4-triazole-1-carboximidamide hydrochloride
[0360] 2-guanidone-4-thiazolidone [0361] 2-guanidinobenzimidazole
[0362] 2-guanidinobenzoxazole [0363] 2-guanidinobenzothiazole
[0364] pyrrolidinoformamidine hydrochloride.
[0365] Among the compounds of formula (III), mention may be made
especially of the following particularly preferred compounds:
[0366] guanidine hydrochloride [0367] guanidine acetate [0368]
guanidine sulfate [0369] guanidine carbonate [0370] guanidine
bicarbonate [0371] guanidine phosphate [0372] guanidine sulfamate
[0373] aminoguanidine hydrochloride [0374] aminoguanidine sulfate
[0375] aminoguanidine bicarbonate [0376] 1,3-diaminoguanidine
hydrochloride [0377] guanylurea phosphate [0378] 1-methylguanidine
hydrochloride [0379] 1,1-dimethylguanidine hydrochloride [0380]
1-ethylguanidine hydrochloride [0381] creatine monohydrate [0382]
creatinine hydrochloride [0383] agmatine [0384] agmatine sulfate
[0385] guanidinoacetic acid [0386] guanidinosuccinic acid [0387]
3-guanidinopropionic acid [0388] .beta.-N-methylguanidinopropionic
acid [0389] N-methylguanidinopropionic acid [0390]
N-(2-hydroxyethyl)guanidine [0391] N-(3-hydroxypropyl)guanidine
[0392] biguanide hydrochloride [0393] N-methylbiguanide
hydrochloride [0394] N-ethylbiguanide hydrochloride [0395]
1,1-dimethylbiguanide hydrochloride [0396]
1,1,3,3-tetramethylguanidine hydrochloride [0397]
2-tert-butyl-1,1,3,3-tetramethylguanidine hydrochloride [0398]
L-arginine [0399] DL-arginine [0400] arginic acid [0401]
N-amidino-N-(2,3-dihydroxypropyl)glycine [0402] N-amidinotaurine
[0403] 2-imino-1-imidazolidineacetic acid [0404]
1H-pyrazole-1-carboxamidine hydrochloride [0405]
3,5-diamino-1H-1,2,4-triazole-1-carboximidamide hydrochloride
[0406] 2-guanidone-4-thiazolidone.
[0407] The term ".alpha.-hydroxy acid and .alpha.-keto acid
derivatives", which may be used as hair-relaxing active agent,
means any derivative selected from the compounds of general
formulae (IV) and (V) below:
##STR00006##
R1 represents H, OH, NH2, CH2-COOH or a linear or branched C1-C4
alkyl radical, R2 represents H, COOH, CHOH--COOH, CF3, CH.dbd.CH2,
NHCONH2, a linear, branched or cyclic C1-C8 alkyl radical
optionally substituted with a radical chosen from OH, Cl, NH2,
COOH, CF3 and SCH3; or a phenyl or benzyl radical optionally
substituted with one OH or OCH3 radical;
##STR00007##
or alternatively the radical
[0408] R1 and R2 may also together form an oxo radical (.dbd.O) or
a cyclopropyl, cyclobutyl, hydroxycyclobutyl, cyclopentyl or
cyclohexyl ring with the carbon atom that bears them, or
alternatively a radical
##STR00008##
when R1=H, R2 may also represent a (CHOH)2CH2OH or (CHOH)3CH2OH
radical, R represents OH or NR3R4 with R3, R4=H or a linear or
branched C1-C4 alkyl radical optionally substituted with one or two
OH radicals and the stereoisomers, organic or mineral salts and
solvates thereof.
[0409] Preferred compounds of formula (IV) that may be mentioned
include:
glycolic acid oxalic acid lactic acid
1-hydroxy-1-cyclopropanecarboxylic acid 2-hydroxy-3-butenoic acid
2-hydroxyisobutyric acid 2-hydroxy-n-butyric acid isoserine
glyceric acid 2-hydroxy-3-methylbutyric acid
2-hydroxy-2-methylbutyric acid 2-hydroxyvaleric acid
4-amino-2-hydroxybutyric acid 1-hydroxycyclohexanecarboxylic acid
dihydroxyfumaric acid citramalic acid tartaric acid citric acid
2-hydroxy-4-(methylthio)butyric acid mandelic acid
2-hydroxy-3-methylvaleric acid glyoxylurea .beta.-imidazolelactic
acid 2-trifluoromethyl-2-hydroxypropionic acid hexahydromandelic
acid 2-hydroxyoctanoic acid arabic acid 3-phenylactic acid
hydroxyphenylglycine 3-hydroxymandelic acid 4-hydroxymandelic acid
2-hydroxynonanoic acid L-arginic acid 3-methoxymandelic acid
4-methoxymandelic acid 3-(4-hydroxyphenyl)lactic acid tartronic
acid tartaric acid .beta.-chlorolactic acid
1-cyclopentanol-1-carboxylic acid
1,2-dihydroxycyclobutanecarboxylic acid 2-ethyl-2-hydroxybutric
acid .alpha.-hydroxyisocaproic acid .alpha.-hydroxycaproic acid
2-hydroxy-3,3-dimethylbutyric acid malic acid hydroxytartronic acid
gluconic acid lactamide
N-methyllactamide
[0410] N-ethyl lactamide
N,N-dimethyllactamide
[0411] N-2-hydroxyethyllactamide and the stereoisomers, organic or
mineral salts and solvates thereof.
[0412] The compounds of formula (IV) that are particularly
preferred are chosen from
glycolic acid oxalic acid L-lactic acid DL-lactic acid D-lactic
acid malic acid tartaric acid DL-glyceric acid arabic acid gluconic
acid hydroxytartronic acid lactamide
N-methyllactamide
[0413] N-ethyl lactamide N-2-hydroxyethyllactamide
[0414] Definition of the .alpha.-keto acid derivatives of general
formula (V):
##STR00009##
R5 represents COOH, a linear or branched C1-C6 alkyl radical
optionally substituted with an OH, COOH or Br radical; a phenyl or
benzyl radical optionally substituted with an OH or COOH radical;
or an indolyl radical or
##STR00010##
and the stereoisomers, organic or mineral salts and solvates
thereof.
[0415] The preferred compounds of formula (V) are chosen from:
pyruvic acid 2-ketobutyric acid .beta.-hydroxypyruvic acid
3-methyl-2-oxobutyric acid 2-oxovaleric acid ketomalonic acid
3-methyl-2-oxovaleric acid trimethylpyruvic acid oxolacetic acid
2-ketoglutaric acid benzylformic acid 2-oxooctanoic acid
2-oxoadipic acid phenylpyruvic acid bromopyruvic acid 2-ketopimelic
acid 4-hydroxyphenylpyruvic acid 3-indoleglyoxalic acid
imidazolopyruvic acid HCl 2-keto-L-gulonic acid
2-carboxy-.alpha.-oxobenzeneacetic acid 3-indolepyruvic acid
2-ketoglutaric acid dihydrate pyruvamide
N-methylpyruvamide
N-ethylpyruvamide
N,N-dimethylpyruvamide
[0416] N-2-hydroxyethylpyruvamide and the stereoisomers, organic or
mineral salts and solvates thereof.
[0417] The compounds of formula (V) that are particularly preferred
are chosen from:
pyruvic acid 2-ketobutyric acid .beta.-hydroxypyruvic acid
ketomalonic acid oxolacetic acid 2-ketoglutaric acid
2-keto-L-gulonic acid 2-ketoglutaric acid dihydrate pyruvamide and
the stereoisomers, organic or mineral salts and solvates
thereof.
[0418] The term "polyhydroxylated aromatic derivatives", which may
be used as hair-relaxing active agent, means any derivative
selected from the compounds of general formula (VI) below:
##STR00011##
in which: [0419] R1, R2, R3 and R4 represent, independently of each
other: [0420] H, F, Cl, Br, OH, OCH.sub.3, OEt, CHO, COCH.sub.3,
COOH, CH.sub.2NH.sub.2, CH.sub.2CH.sub.2NH.sub.2, CH.sub.2OH,
CH.sub.2CH.sub.2OH, CH.sub.2COCH.sub.3, CH.sub.2COOH,
CH.sub.2CH.sub.2COOH, CH.sub.2CONH.sub.2, CHOH--CH.sub.2CH,
--CH(NH.sub.2) COOH, NHCOCH.sub.3, COCH.sub.2CH.sub.3, CONH.sub.2
[0421] or alternatively a linear or branched C1-C5 alkyl radical
when the two OH radicals are in a meta position and when R1, R2 and
R3 represent a hydrogen atom, R4 may also represent NH.sub.2, and
the stereoisomers, organic or mineral salts and solvates
thereof.
[0422] The preferred compounds of formula (VI) are chosen from:
catechol resorcinol 4-methylcatechol 3-methylcatechol
2-methylresorcinol 5-methylresorcinol 4-methylresorcinol pyrogallol
1,2,4-trihydroxybenzene phloroglucinol 3-fluorocatechol
4-fluorocatechol 4-fluororesorcinol 2,3-dihydroxybenzaldehyde
3,4-dihydroxybenzaldehyde 2,4-dihydroxybenzaldehyde
3,5-dihydroxybenzaldehyde 4-ethylcatechol 4-ethylresorcinol
2,5-dimethylresorcinol 4,5-dimethylresorcinol
2,4-dimethyl-1,3-benzenediol 3,4-dihydroxybenzylamine
3,5-dihydroxybenzylamine 3-methoxycatechol 5-methylpyrogallol
3,4-dihydroxybenzyl alcohol 5-methoxyresorcinol
2,4,6-trihydroxytoluene 3,5-dihydroxybenzyl alcohol
2-methoxyresorcinol 5-methylpyrogallol 4-methoxyresorcinol
3,5-dihydroxytoluene monohydrate 4-chlorocatechol 3-chlorocatechol
4-chlororesorcinol 2-chlororesorcinol 3',4'-dihydroxyacetophenone
2',3'-dihydroxyacetophenone 2',6'-dihydroxyacetophenone
2',4'-dihydroxyacetophenone 3',5'-dihydroxyacetophenone
2,6-dihydroxy-4-methylbenzaldehyde 3-isopropylcatechol
4-isopropylcatechol 4-propylresorcinol
2,4-dihydroxy-1,3,5-trimethylbenzene 3,4-dihydroxybenzamide
3,5-dihydroxybenzamide 2,6-dihydroxybenzamide
2,4-dihydroxybenzamide 3-hydroxytyramine 2,3-dihydroxybenzoic acid
3,4-dihydroxybenzoic acid 2,4-dihydroxybenzoic acid
2,6-dihydroxybenzoic acid 3,5-dihydroxybenzoic acid
2,3,4-trihydroxybenzaldehyde 2,4,6-trihydroxybenzaldehyde
3,4,5-trihydroxybenzaldehyde 2,4,5-trihydroxybenzaldehyde
2-(3,4-dihydroxyphenyl)ethanol 2,4,6-trihydroxy-1,3-dimethylbenzene
2,6-dihydroxy-4-methylbenzyl alcohol
2-fluoro-3,4-dihydroxybenzaldehyde
3,4-dihydroxy-6-fluorobenzaldehyde 2-methoxyphloroglucinol
3,5-dihydroxyanisole hydrate 4-aminoresorcinol hydrochloride
2-aminoresorcinol hydrochloride 5-aminobenzene-1,3-diol
hydrochloride phloroglucinol dihydrate 3',4'-dihydroxypropiophenone
3,4-dihydroxyphenylacetone (2,3-dihydroxyphenyl)acetone
2',4'-dihydroxypropiophenone 2',4'-dihydroxy-3'-methylacetophenone
(2,4-dihydroxyphenyl)acetone (3,5-dihydroxyphenyl)acetone
2,6-dihydroxy-4'-methylacetophenone 4-tert-butylcatechol
4-N-butylresorcinol
[0423] 2,4-diethyl-1,3-benzenediol 3,4-dihydroxyphenylacetamide
3-hydroxyacetaminophen 2',3',4'-trihydroxyacetophenone
3,4-dihydroxyphenylacetic acid 2,3-dihydroxy-4-methoxybenzaldehyde
3,4-dihydroxy-5-methoxybenzaldehyde 2',3',4'-trihydroxyacetophenone
2',4',6'-trihydroxyacetophenone 3,5-dihydroxy-4-methylbenzoic acid
2,6-dihydroxy-4-methylbenzoic acid 2,4-dihydroxy-6-methylbenzoic
acid 3,5-dihydroxyphenylacetic acid
2-ethyl-5-methoxybenzene-1,3-diol 3,4,5,-trihydroxybenzamide
4-amino-3,5-dihydroxybenzoic acid 2,3,4-trihydroxybenzoic acid
2,3,4-trihydroxybenzoic acid gallic acid 2,4,6-trihydroxybenzoic
acid 3,4-dihydroxyphenyl glycol 1,2-dihydroxy-4,5-dimethoxybenzene
3,5-dihydroxyacetophenone monohydrate 3,4-dihydroxybenzoic acid
monohydrate 3,4,5-trihydroxybenzaldehyde hexahydroxybenzene
3,5-dihydroxybenzylamine hydrochloride 4,6-diaminoresorcinol
hydrochloride 4,5-dichlorocatechol 3,5-dichlorocatechol
4,6-dichlororesorcinol 2',4'-dihydroxy-3'-methylpropiophenone
1-(3-ethyl-2,6-dihydroxyphenyl)ethan-1-one
3-(3,4-dihydroxyphenyl)propionic acid
(2,3,4-trihydroxyphenyl)acetone (2,4,5-trihydroxyphenyl)acetone
(3,4,5-trihydroxyphenyl)acetone
2',6'-dihydroxy-4'-methoxyacetophenone
1-(2,6-dihydroxy-3-methoxyphenyl)ethan-1-one
3(2,4-dihydroxyphenylpropionic acid
2,4-dihydroxy-3,6-dimethylbenzoic acid
(2,3,4-trihydroxyphenyl)acetone (2,4,5-trihydroxyphenyl)acetone
(2,4,6-trihydroxyphenyl)acetone (3,4,5-trihydroxyphenyl)acetone
3,4-dihydroxymandelic acid 5-hydroxyisovanillic acid
3,4,5-trihydroxybenzamide hydrate 4-bromocatechol and the
stereoisomers, organic or mineral salts and solvates thereof.
[0424] The compounds of formula (VI) that are particularly
preferred are chosen from:
resorcinol 2-methylresorcinol 5-methylresorcinol 4-methylresorcinol
pyrogallol 1,2,4-trihydroxybenzene 4-ethylresorcinol
2,5-dimethylresorcinol 4,5-dimethylresorcinol
2,4-dimethyl-1,3-benzenediol 3,4-dihydroxybenzylamine
3,5-dihydroxybenzylamine 5-methylpyrogallol 3,4-dihydroxybenzyl
alcohol 5-methoxyresorcinol 2,4,6-trihydroxytoluene
3,5-dihydroxybenzyl alcohol 2-methoxyresorcinol 5-methylpyrogallol
4-methoxyresorcinol 3,5-dihydroxytoluene monohydrate
4-propylresorcinol 2,4-dihydroxy-1,3,5-trimethylbenzene
3,4-dihydroxybenzamide 3,5-dihydroxybenzamide
2,6-dihydroxybenzamide 2,4-dihydroxybenzamide 3-hydroxytyramine
2,3-dihydroxybenzoic acid 3,4-dihydroxybenzoic acid
2,6-dihydroxybenzoic acid 3,5-dihydroxybenzoic acid
2-(3,4-dihydroxyphenyl)ethanol 2,4,6-trihydroxy-1,3-dimethylbenzene
2,6-dihydroxy-4-methylbenzyl alcohol 2-methoxyphloroglucinol
3,5-dihydroxyanisole hydrate 4-aminoresorcinol hydrochloride
2-aminoresorcinol hydrochloride 5-aminobenzene-1,3-diol
hydrochloride phloroglucinol dihydrate 2,4-diethyl-1,3-benzenediol
3,4-dihydroxyphenylacetamide 3,4-dihydroxyphenylacetic acid
3,5-dihydroxy-4-methylbenzoic acid 2,6-dihydroxy-4-methylbenzoic
acid 2,4-dihydroxy-6-methylbenzoic acid 3,5-dihydroxyphenylacetic
acid 2-ethyl-5-methoxybenzene-1,3-diol 3,4,5-trihydroxybenzamide
4-amino-3,5-dihydroxybenzoic acid 3,4-trihydroxybenzoic acid gallic
acid 2,4,6-trihydroxybenzoic acid DL-3,4-dihydroxyphenyl glycol
1,2-dihydroxy-4,5-dimethoxybenzene 3,4-dihydroxybenzoic acid
monohydrate hexahydroxybenzene 3,5-dihydroxybenzylamine
hydrochloride sodium .gamma.-resorcylate sodium .beta.-resorcylate
4,6-diaminoresorcinol hydrochloride
3-(3,4-dihydroxyphenyl)propionic acid
2,4-dihydroxy-3,6-dimethylbenzoic acid DL-3,4-dihydroxymandelic
acid hydroxyisovanillic acid 3,4,5-trihydroxybenzamide acid hydrate
gallic acid monohydrate and the stereoisomers, organic or mineral
salts and solvates thereof.
[0425] The term "cyclic and linear amide derivatives" which may be
used as hair-relaxing active agent, means any derivative selected
from the compounds of general formulae (VII) and (VIII) below:
##STR00012##
with
X=0 to 3
[0426] R1, R2, R3, R4, R5 and R6, which may be identical or
different, possibly taking the following meaning: [0427] H, [0428]
F, [0429] linear or branched C1-C30 alkyl, possibly comprising one
or more unsaturations, [0430] optionally interrupted with --O--,
--S--, --NR7-, --C(O)--, --OC(O)--, --C(O)O--, --C(O)NR7-,
--NR7C(O)--, --OC(O)NR7-, --NR7C(O)O--, --NR7C(O)NR8-, --NR7SO2-,
--NR7SO2NR8-, --SO2NR7-, --OSO2-, --C(S)NR7-, --NR7C(S)--, [0431]
optionally substituted with --OR7, --SR7, --NR7R8, --C(O)R7,
--OC(O)R7, --C(O)OR7, --C(O)NR7R8, --NR7C(O)R8, --OC(O)NR7R8,
--NR7C(O)OR8, --NR7C(O)NR8R9, --NR7SO2R8, --NR7SO2NR8R9,
--SO2NR7R8, --OSO2R7, --C(S)NR7R8, --NR7C(S)R8, an aromatic or
non-aromatic, heterocyclic or non-heterocyclic ring, possibly
containing 3 to 10 atoms, [0432] --OR7, --SR7, --NR7R8, --C(O)R7,
--OC(O)R7, --C(O)OR7, --C(O)NR7R8, --NR7C(O)R8, --OC(O)NR7R8,
--NR7C(O)OR8, --NR7C(O)NR8R9, --NR7SO2R8, --NR7SO2NR8R9,
--SO2NR7R8, --C(S)NR7R8, --NR7C(S)R8, [0433] an aromatic or
non-aromatic, heterocyclic or non-heterocyclic ring, possibly
containing 3 to 10 carbon atoms, which is optionally substituted,
[0434] R1, R2, R3, R4, R5 and R6 possibly forming in pairs, with
the carbon atoms to which they are attached, a (hetero)cycle of 3
to 7 atoms, optionally interrupted with O, S, N, --C(O)--,
--C(O)O--, --C(O)NR7--, [0435] R1R2, R3R4, and R5R6 possibly being
combined in pairs to form an oxo function, R7, R8 and R9, which may
be identical or different, possibly taking the following meaning:
[0436] H, F, optionally substituted linear or branched C1-C30
alkyl, possibly containing one or more unsaturations, [0437] one of
the 20 natural N-branched amino acids, C-protected with standard
protecting groups or one of the 20 natural C-branched amino acids,
N-protected with standard protecting groups, [0438] an aromatic or
non-aromatic, heterocyclic or non-heterocyclic ring, possibly
containing 3 to 10 atoms, and also the stereoisomers, organic or
mineral salts and solvates thereof.
[0439] The preferred compounds of formula (VII) are chosen
from:
2-pyrrolidone 3-methyl-2-pyrrolidone pyroglutamic acid
5-methyl-2-pyrrolidone succinimide
1-methyl-.alpha.-phenylsuccinimide ethyl pyroglutamate
2-oxo-4-phenylpyrrolidine-3-carboxylic acid
pyrrolidonyl-4-butyramide 5-(hydroxymethyl)-2-pyrrolidinone methyl
pyroglutamate ethyl 2-oxo-4-phenyl-3-pyrrolidinecarboxylate
4-(hydroxy)-4-methylpyrrolidin-2-one
4-fluoro-5-pyrrolidone-2-carboxylic acid
4,4-pentamethylene-2-pyrrolidinone
[(5-oxopyrrolidine-2-carbonyl)amino]acetic acid
2-[(5-oxopyrrolidine-2-carbonyl)amino]-3-phenylpropionic acid
5-methoxy-2-pyrrolidinone 2-azabicyclo[2.2.1]hept-5-en-3-one butyl
2-pyrrolidone-5-carboxylate octyl 2-pyrrolidone-5-carboxylate
4-carbamoyl-2-[(5-oxopyrrolidin-2-carbonyl)amino]-butyric acid
4-hydroxy-2-pyrrolidinone 2-dimethylamino ethyl
5-oxopyrrolidine-2-carboxylate
3-(1H-indol-3-yl)-2-[(5-oxopyrrolidin-2-carbonyl)-amino]propionic
acid 5-pyridin-3-ylpyrrolidin-2-one 2-azabicyclo[2.2.1]heptan-3-one
methyl 2-[3-(methoxymethyl)-5-oxo-2-pyrrolidinyl]-acetate
4-phenyl-2-pyrrolidinone 4-spiro-[3-[(2-pyrrolidonone)]piperidine
(4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
2-amino-5-oxo-5-(5-oxopyrrolidin-2-yl)pentanoic acid
2-(2,5-dioxopyrrolidin-3-ylsulfanyl)nicotinic acid
3-hydroxynorcotinine 3-benzyl-5-hydroxymethylpyrrolin-2-one ethyl
4-methylpyroglutamate ethyl 4-ethylpyroglutamate ethyl
4-isopropylpyroglutamate ethyl 4-benzylpyroglutamate
3-ethyl-5-hydroxymethylpyrrolidin-2-one
5-hydroxymethyl-3-methylpyrrolidin-2-one
5-oxopyrrolidine-3-carboxylic acid
5-hydroxymethyl-3-isopropylpyrrolidin-2-one
5-hydroxymethylpyrrolidin-2-one 5-aminomethylpyrrolidin-2-one ethyl
2-oxopyrrolidine-3-carboxylate 3-hydroxypyrrolidin-2-one
3-ethyl-4-methylpyrroline-2-one
3,4-(1,3-propanediyl)-2-pyrrolidinone .delta.-valerolactam
3-carbethoxy-2-piperidone glutarimide 3,3-dimethylglutarimide
3-ethyl-3-methylglutarimide 6-methyl-2-piperidone
3-methylpiperidin-2-one
D-mannono-D-lactam
[0440] N-(2-aminoethyl)-2-oxopiperidine-3-carboxamide
4-phenyl-.delta.-valerolactam 3-amino-4-phenyl-.delta.-valerolactam
4-methyl-3-phenyl-.delta.-valerolactam
3-methyl-5-phenyl-.delta.-valerolactam
3-(2-isopropoxycarbonylethyl)-6-oxopiperidine-3-carboxylic acid
3-(2-benzylcarbamoylethyl)-6-oxopioperidine-3-carboxylic acid
methyl-2-oxopiperidine-3-carboxylate
3,4,5-trihydroxy-6-oxo-2-piperidinecarboxylic acid
2-piperidinone-6-carboxylic acid 5-hydroxypiperidin-2-one ethyl
5-methyl-2-oxo-3-piperidinecarboxylate 6-oxopiperidine-2-carboxylic
acid 4-hydroxypiperidin-2-one 2-azetidinone .epsilon.-caprolactam
and the stereoisomers, organic or mineral salts and/or solvates
thereof.
[0441] The compounds of formula (VII) that are particularly
preferred are chosen from:
2-pyrrolidone pyroglutamic acid 3-methyl-2-pyrrolidone
5-methyl-2-pyrrolidone 5-(hydroxymethyl)-2-pyrrolidinone
5-oxopyrrolidine-3-carboxylic acid 5-aminomethylpyrrolidin-2-one
4-hydroxy-2-pyrrolidinone and the stereoisomers, organic or mineral
salts and/or solvates thereof. Definition of the linear amides of
general formula (VIII)
##STR00013##
with
X=0 or 1;
if X=0
[0442] R2 possibly taking the following meaning: [0443] H [0444] F,
Cl [0445] an optionally substituted, heterocyclic or
non-heterocyclic, aromatic or non-aromatic ring, which may contain
3 to 10 atoms, [0446] --OR7, --SR7, --C(O)R7, --OC(O)R7, --C(O)OR7,
--C(O)NR7R8, --OC(O)NR7R8, --SO2NR7R8, --C(S)NR7R8, R3 possibly
taking the following meaning: [0447] H, except if R2 is 3-pyridine
[0448] linear or branched C1-C30 alkyl, possibly comprising one or
more unsaturations, [0449] optionally interrupted with --O--,
--S--, --NR7-, --C(O)--, --OC(O)--, --C(O)O--, --C(O)NR7-,
--NR7C(O)--, --OC(O)NR7-, --NR7C(O)O--, --NR7C(O)NR8-, --NR7SO2-,
--NR7SO2NR8-, --SO2NR7-, --OSO2-, --C(S)NR7-, --NR7C(S)--, [0450]
optionally substituted with: [0451] F, Cl [0452] --OR7, --SR7,
--NR7R8, --C(O)R7, --OC(O)R7, --C(O)OR7, --C(O)NR7R8, --NR7C(O)R8,
--OC(O)NR7R8, --NR7C(O)OR8, --NR7C(O)NR8R9, --NR7SO2R8,
--NR7SO2NR8R9, --SO2NR7R8, --OSC2R7, --C(S)NR7R8, --NR7C(S)R8
[0453] a heterocyclic or non-heterocyclic, aromatic or non-aromatic
ring, possibly containing 3 to 10 atoms, R7, R8 and R9, which may
be identical or different, possibly taking the following meaning:
[0454] H, [0455] linear or branched C1-C30 alkyl, possibly
comprising one or more unsaturations, [0456] one of the 20 natural
N-branched amino acids, C-protected with standard protecting
groups, or one of the 20 natural C-branched amino acids,
N-protected with standard protecting groups, [0457] a heterocyclic
or non-heterocyclic, aromatic or non-aromatic ring, possibly
containing 3 to 10 atoms,
if X=1
[0458] R1 possibly taking the following meaning: [0459] linear or
branched C1-C30 alkylene, possibly containing one or more
unsaturations, [0460] optionally interrupted with --O--, --S--,
--NR7-, --C(O)--, --OC(O)--, --C(O)O--, --C(O)NR7-, --NR7C(O)--,
--OC(O)NR7-, --NR7C(O)O--, --NR7C(O)NR8-, --NR7SO2-, --NR7SO2NR8-,
--SO2NR7-, --OSO2-, --C(S)NR7-, --NR7C(S)--, [0461] optionally
substituted with: [0462] F, Cl [0463] --OR7, --SR7, --NR7R8,
--C(O)R7, --OC(O)R7, --C(O)OR7, --C(O)NR7R8, --NR7C(O)R8,
--OC(O)NR7R8, --NR7C(O)OR8, --NR7C(O)NR8R9, --NR7SO2R8,
--NR7SO2NR8R9, --SO2NR7R8, --OSC2R7, --C(S)NR7R8, --NR7C(S)R8,
[0464] an aromatic or non-aromatic, heterocyclic or
non-heterocyclic ring, possibly containing 3 to 10 atoms, with the
exception of hydroxyl or oxo substituents in a position alpha to
the amide function R2 possibly taking the following meaning: [0465]
H [0466] F, Cl [0467] an aromatic or non-aromatic, heterocyclic or
non-heterocyclic ring, which is optionally substituted, possibly
containing 3 to 10 atoms, [0468] --OR7, --SR7, --NR7R8, --C(O)R7,
--OC(O)R7, --C(O)OR7, --C(O)NR7R8, --NR7C(O)R8, --OC(O)NR7R8,
--NR7C(O)OR8, --NR7C(O)NR8R9, --NR7SO2R8, --NR7SO2NR8R9,
--SO2NR7R8, --C(S)NR7R8, --NR7C(S)R8 R3 possibly taking the
following meaning: [0469] H [0470] linear or branched C1-C30 alkyl,
possibly containing one or more unsaturations, [0471] optionally
interrupted with --O--, --S--, --NR7-, --C(O)--, --OC(O)--,
--C(O)O--, --C(O)NR7-, --NR7C(O)--, --OC(O)NR7-, --NR7C(O)O--,
--NR7C(O)NR8-, --NR7SO2-, --NR7SO2NR8-, --SO2NR7-, --OSO2-,
--C(S)NR7-, --NR7C(S)--, [0472] optionally substituted with: [0473]
F, Cl [0474] --OR7, --SR7, --NR7R8, --C(O)R7, --OC(O)R7, --C(O)OR7,
--C(O)NR7R8, --NR7C(O)R8, --OC(O)NR7R8, --NR7C(O)ORB,
--NR7C(O)NR8R9, --NR7SO2R8, --NR7SO2NR8R9, --SO2NR7R8, --OSO2R7,
--C(S)NR7R8, --NR7C(S)R8 [0475] an aromatic or non-aromatic,
heterocyclic or non-heterocyclic ring, possibly containing 3 to 10
atoms, R7, R8 and R9, which may be identical or different, possibly
taking the following meaning: [0476] H, [0477] linear or branched
C1-C30 alkyl, possibly containing one or more unsaturations, [0478]
one of the 20 natural N-branched amino acids, C-protected with
standard protecting groups, or one of the 20 natural C-branched
amino acids, N-protected with standard protecting groups, [0479] an
aromatic or non-aromatic, heterocyclic or non-heterocyclic ring,
possibly containing 3 to 10 atoms, if R2(R1)x represents a fatty
acid-based saturated or unsaturated alkyl radical, this alkyl
radical contains less than 16 carbon atoms, and also the
stereoisomers thereof and the organic or mineral salts and solvates
thereof.
[0480] Preferably, if R2(R1)x represents a fatty acid-based
saturated or unsaturated alkyl radical, this alkyl radical contains
fewer than 9 carbon atoms.
[0481] The preferred compounds of formula (VIII) are chosen
from:
acetamide
N-methylacetamide
[0482] propionamide
N-ethylacetamide
N-methylpropionamide
N-butyramide
N-(hydroxymethyl)acetamide
[0483] methoxyacetamide hydracrylamide 2-mercaptoacetamide
acetoacetamide
N--(N-propyl)acetamide
N-ethylpropionamide
[0484] valeramide malonamide
N-acetylethylenediamine
[0485] 2-amino-N-ethylacetamide
N-acetylethanolamine
[0486] 3-chloropropionamide glycinamide
N-(cyclopropylmethyl)acetamide
N-methylacetoacetamide
[0487] 1-acetamidoacetone
N-methylvaleramide
N-butylacetamide
[0488] hexanamide
N-acetylglycinamide
[0489] succinamide N-ethyl-2-methylaminoacetamide
N-acetylglycine
[0490] succinamic acid methylcarbamoylacetate
N-(2-hydroxyethyl)propionamide N1-(3-hydroxypropyl)acetamide
5-hydroxyvaleramide 3-amino-3-thioxopropanamide
C-(2-hydroxyethyl)glycolamide 3,4-dihydroxybutyramide
N-(2-chloroethyl)acetamide N-(3-methylbutyl)acetamide
N-methylsuccinamic acid ethyl carbamoylacetate glycylglycine
asparagine 2-amino-N-(2-methoxyethyl)acetamide
2-(2-amino-2-oxoethoxy)acetic acid 2-phenylacetamide
pyridine-2-acetamide pyridine-4-acetamide methylsulfonylacetamide
4-aminobutyramide 5-acetaminomethyltetrazole thiphene-2-acetamide
4-thiazoleacetamide 1-aminocyclopentanacetamide
2-piperazin-1-ylacetamide
N-octanamide
[0491] N,N'-diacetylethylenediamine adipamide 2-morpholinoacetamide
ethyl acetamidoacetate 4-acetamidbutyric acid 2-(acetylamino)ethyl
acetate N-(2-hydroxyethyl)acetoacetamide isopropyl carbamoylacetate
2-amino-N-methylsuccinamic acid glutamine
N-(2-methoxyethyl)-2-methylaminoacetamide
N-methyl-2-phenylacetamide
N-benzylacetamide
[0492] N-propylpyrrolidine-2-carboxamide
N-(tert-butyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxamide
N,N-butylpropionamide
[0493] N-1,3,3-trimethylbutanamide
N-.alpha.-acetyl-L-lysine-N-methylamide L-proline N-octylamide and
also the stereoisomers thereof and the organic or mineral salts and
solvates thereof, and also the following amino acids and
derivatives:
AC-ALA-NHME
AC-.beta.-ALA-OH
AC-.beta.-ALA-OME
AC-GLY-NHME
AC-HIS-NHME
AC-ILE-NHME
AC-LEU-GLY-OH
AC-LEU-NHME
AC-LYS-NHME
AC-PHE-NHME
AC-SER-GLY-OH
AC-VAL-NHME
H-.beta.-ALA-GLY-OH
H-.beta.-ALA-NH2
H-GLY-O-ALA-OH
H-GLY-NHME
H-PRO-ALA-OH
H-PRO-ALA-OH
H-PRO-.beta.-ALA-OH
H-PRO-GLY-NH2
H-PRO-GLY-OH
H-PRO-GLY-OH
H-PRO-ILE-OH
H-PRO-LEU-OH
H-PRO-NHCH3
H-PRO-NHET
H-PRO-SER-OH
H-PRO-VAL-OH
H-PRO-VAL-OH
SAR-GLY-OH
SAR-NH2
[0494] and also the stereoisomers thereof and the organic or
mineral salts and solvates thereof.
[0495] The compounds of formula (VIII) that are particularly
preferred are chosen from:
glycinamide acetamide
N-methylacetamide
N-ethylacetamide
[0496] propionamide
N-ethylpropionamide
[0497] and also the stereoisomers thereof and the organic or
mineral salts and solvates thereof.
[0498] In the compositions according to the invention intended for
a process of relaxing, uncurling or straightening the hair, the
mixture in any proportion of at least two denaturing agents as
defined previously is advantageously present in an overall molar
concentration of between 1 M and 8 M and more advantageously in a
concentration of between 2 M and 8M.
[0499] In the process according to the invention and in the kit,
the pH of the compositions is preferably less than 9 and more
preferentially less than 7.
[0500] The compositions according to the invention are either in
the form of an aqueous solution or in the form of a thickened cream
so as to keep the hair as straight as possible. These creams are
prepared in the form of "heavy" emulsions.
[0501] For the purpose of improving the cosmetic properties of
keratin fibres or to attenuate or avoid their degradation, the
composition used according to the invention may also comprise one
or more additional cosmetic active agents. Generally, the said
additional cosmetic active agent(s) represent(s) from 0.01% to 30%
and preferably from 0.1% to 10% by weight relative to the total
weight of the cosmetic composition.
[0502] Generally, the composition applied to the keratin fibres is
applied in an amount of from 0.05 to 20 g and preferably from 0.1
to 10 g of composition per gram of dry keratin fibre.
[0503] After applying the composition, and before raising the
temperature of the keratin fibres using a heating means, the said
composition may be left to act, generally for 30 seconds to 60
minutes and preferably 5 to 45 minutes.
[0504] The process according to the invention includes, after the
step of applying the composition, a step of raising the temperature
of the keratin fibres, using a heating means, to a temperature of
between 110.degree. C. and 250.degree. C.
[0505] Advantageously, an iron is used as heating means.
[0506] For the purposes of the present invention, the term "iron"
means a device for heating keratin fibres that places the said
fibres and the heating device in contact, the end of the iron that
comes into contact with the hair generally having two flat
surfaces. These two flat surfaces may be metallic. They may be
smooth or crinkled.
[0507] As examples of irons that may be used in the process
according to the invention, mention may be made of flat irons of
any type, and in particular, in a non-limiting manner, those
described in patents U.S. Pat. No. 5,957,140 and U.S. Pat. No.
5,046,516.
[0508] The iron may be applied by successive separate touches of a
few seconds, or by gradually moving or sliding it along the
locks.
[0509] Preferably, in the process according to the invention, the
iron is applied by continuous movement from the root to the end, in
one or more passes.
[0510] The process according to the invention may also include an
additional step of partial predrying of the keratin fibres before
the step of raising the temperature, so as to avoid substantial
evolution of steam that might burn the stylist's hands and the
individual's scalp.
[0511] This predrying step may take place, for example, using a
hairdryer, a hood or alternatively by drying in the open air.
[0512] The invention especially concerns processes in which the
composition comprises at least one of the following combinations:
[0513] at least one denaturing agent is a guanidine corresponding
to formula (III) and at least one denaturing agent corresponds to
formula (V), [0514] at least one denaturing agent is a urea
corresponding to formula (I) and at least one denaturing agent
corresponds to formula (III), [0515] at least one denaturing agent
is a urea corresponding to formula (I) and at least one denaturing
agent corresponds to formula (V).
[0516] The invention also relates to a kit comprising at least:
[0517] one heating means that affords a temperature of between 110
and 250.degree. C., [0518] one hair-relaxing composition containing
at least two denaturing agents.
[0519] The invention also relates to a kit comprising at least:
[0520] one heating means that affords a temperature of between 110
and 250.degree. C., [0521] a first hair-relaxing composition
containing at least one denaturing agent, [0522] a second
hair-relaxing composition containing at least one denaturing
agent.
[0523] The invention may be understood more clearly with the aid of
the non-limiting examples that follow, which constitute
preferential embodiments of the compositions according to the
invention.
[0524] The compositions may be applied as a mixture (see Example 1
and 2) or successively (see Example 3).
EXAMPLE 1
[0525] A simplified hair-relaxing composition is prepared,
containing a mixture of guanidine hydrochloride at a concentration
of 2 M and of pyruvic acid at a concentration of 2 M, in water, as
hair-relaxing active agent. This composition is applied to
naturally curly African hair for 15 minutes at a temperature of
40.degree. C., and the hair is then rapidly towel-dried.
[0526] Lock-by-lock straightening of the head of hair is then
performed using a flat iron heated to 180.degree. C., for 10 to 15
seconds. The hair is efficiently relaxed and feels soft.
EXAMPLE 2
[0527] A simplified hair-relaxing composition is prepared,
containing a mixture of guanidine hydrochloride at a concentration
of 4 M and of urea at a concentration of 4 M, in water, as
hair-relaxing active agent. This composition is applied to
naturally curly African hair for 15 minutes at a temperature of
40.degree. C., and the hair is then rapidly towel-dried.
[0528] Lock-by-lock straightening of the head of hair is then
performed using a flat iron heated to 180.degree. C., for 10 to 15
seconds. The hair is efficiently relaxed and feels soft.
EXAMPLE 3
[0529] A simplified hair-relaxing composition is prepared,
containing urea at a concentration of 2 M in water, as
hair-relaxing active agent. This composition is applied to
naturally curly African hair for 15 minutes at a temperature of
40.degree. C., and the hair is then rapidly towel-dried. A second
simplified hair-relaxing composition is prepared, containing
pyruvic acid at a concentration of 2 M, in water, as hair-relaxing
active agent. This composition is applied to the same hair for 15
minutes at a temperature of 40.degree. C., and the hair is then
rapidly towel-dried. Lock-by-lock straightening of the head of hair
is then performed using a flat iron heated to 180.degree. C., for
10 to 15 seconds. The hair is efficiently relaxed and feels
soft.
* * * * *