U.S. patent application number 12/637457 was filed with the patent office on 2010-04-15 for polyamino acid derivatives and use thereof in compositions for treating keratin fibers.
This patent application is currently assigned to L'Oreal S.A.. Invention is credited to Christian Blaise, Michel PHILIPPE.
Application Number | 20100092405 12/637457 |
Document ID | / |
Family ID | 9524685 |
Filed Date | 2010-04-15 |
United States Patent
Application |
20100092405 |
Kind Code |
A1 |
PHILIPPE; Michel ; et
al. |
April 15, 2010 |
POLYAMINO ACID DERIVATIVES AND USE THEREOF IN COMPOSITIONS FOR
TREATING KERATIN FIBERS
Abstract
##STR00001## The invention concerns the use in a cosmetic
composition of at least a poly-aminoacid of general formula (1) in
which X is --O--, --S-- or --NR.sub.3; R represents in particular a
hydrogen atom or a C.sub.1-C.sub.10 alkyl radical; R.sub.2
represents in particular a hydrogen atom or an optionally
substituted alkyl radical; R.sub.3 represents a hydrogen atom or an
alkyl radical; R.sub.4 represents a hydrogen atom or a radical such
as NH.sub.2, OH, SH, --CHOHCH.sub.3, --CONH.sub.2; n is a number
greater than 1 such that the poly-aminoacid derivative molecular
weight ranges between 200 and 200000. The invention also concerns
the use of said derivatives for keratinous fibre strengthening and
care.
Inventors: |
PHILIPPE; Michel; (Wissous,
FR) ; Blaise; Christian; (Saint Mande, FR) |
Correspondence
Address: |
FINNEGAN, HENDERSON, FARABOW, GARRETT & DUNNER;LLP
901 NEW YORK AVENUE, NW
WASHINGTON
DC
20001-4413
US
|
Assignee: |
L'Oreal S.A.
|
Family ID: |
9524685 |
Appl. No.: |
12/637457 |
Filed: |
December 14, 2009 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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11984382 |
Nov 16, 2007 |
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12637457 |
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10682783 |
Oct 10, 2003 |
7316815 |
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11984382 |
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09647493 |
Dec 14, 2000 |
6656458 |
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PCT/FR99/00256 |
Feb 5, 1999 |
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10682783 |
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Current U.S.
Class: |
424/47 ; 424/59;
424/70.1; 514/400; 514/562; 514/563; 514/614; 514/626 |
Current CPC
Class: |
A61K 8/44 20130101; A61Q
5/12 20130101; A61K 8/88 20130101; Y10S 514/881 20130101; Y10S
514/88 20130101; A61K 31/421 20130101; Y10S 514/945 20130101; A61Q
5/02 20130101; Y10S 514/937 20130101; Y10S 514/944 20130101; A61Q
5/00 20130101 |
Class at
Publication: |
424/47 ; 514/626;
514/614; 514/563; 514/562; 514/400; 424/70.1; 424/59 |
International
Class: |
A61K 8/40 20060101
A61K008/40; A61K 8/42 20060101 A61K008/42; A61K 8/36 20060101
A61K008/36; A61Q 5/00 20060101 A61Q005/00; A61Q 17/04 20060101
A61Q017/04 |
Foreign Application Data
Date |
Code |
Application Number |
Mar 31, 1998 |
FR |
98/03965 |
Claims
1-27. (canceled)
28. A method for strengthening keratin fibers, comprising applying
to said keratin fibers a cosmetic composition comprising at least
one polyamino acid of formula (I): ##STR00016## wherein X is chosen
from --O--, --S-- and --NR.sub.5 --; R.sub.1 is chosen from: (i)
linear and branched, saturated and unsaturated, C.sub.1-C.sub.40
alkyl groups, optionally substituted with at least one substituent
chosen from a hydroxyl group and ##STR00017## wherein said alkyl
groups are optionally interrupted with at least one hetero atom,
and r' and r'', which are identical or different, are each chosen
from a hydrogen atom and C.sub.1-C.sub.6 alkyl groups; and
##STR00018## wherein s is 0 to 4; R.sub.2 is chosen from a hydrogen
atom, C.sub.1-C.sub.8 alkyl groups, a --CH.sub.2C.sub.6H.sub.5
group, a --CH.sub.2C.sub.6H.sub.5 pOH group, wherein pOH is
para-OH, a --CH.sub.2OH group, a --CHOH--CH.sub.3 group
and-(CH.sub.2).sub.t-NH.sub.2 groups, wherein t is chosen from 3, 4
and 5; R.sub.3 and R.sub.5 which may be identical or different, are
each chosen from a hydrogen atom and C.sub.1-C.sub.6 alkyl groups;
R.sub.4 is chosen from a hydrogen atom, NH.sub.2, OH, SH,
--CHOHCH.sub.3, --CON H.sub.2, ##STR00019## --C.sub.6H.sub.5 and
--C.sub.6H5 pOH, wherein pOH is para-OH; and n is an average number
greater than 1 such that the molecular weight of the polyamino acid
of formula (I) ranges from 200 to 200,000, wherein the n repeating
units may be identical or different; or a salt of said polyamino
acid, with the proviso that if X is NH, R.sub.2 is H, and R.sub.3
is CH.sub.3, then R.sub.1 is not
C.sub.15H.sub.31--CH(OH)--CH(CH.sub.2OH) and R.sub.1 is not a
C.sub.8.sup.-C.sub.24 alkyl group.
29. The method according to claim 28, wherein said cosmetic
composition comprises said at least one polyamino acid in an amount
ranging from 0.001% to 30% by weight relative to the total weight
of said cosmetic composition.
30. The method according to claim 28, wherein said cosmetic
composition comprises said at least one polyamino acid in an amount
ranging from 0.01% to 15% by weight relative to the total weight of
the composition.
31. The method according to claim 28, wherein said cosmetic
composition is in the form of a shampoo, said cosmetic composition
further comprising a cosmetic vehicle chosen from aqueous solutions
and aqueous-alcoholic solutions.
32. The method according to claim 31, wherein said shampoo further
comprises at least one surfactant in an amount from 0.01% to 50% by
weight relative to the total weight of the shampoo.
33. The method according to claim 28, wherein said cosmetic
composition is in the form of a mousse, said cosmetic composition
further comprising a cosmetic vehicle chosen from a fatty phase and
aqueous-alcoholic solutions.
34. The method according to claim 33, wherein said mousse further
comprises at least one foaming agent and at least one
propellant.
35. The method according to claim 34, wherein said at least one
foaming agent is present in an amount ranging from 0.05% to 20% by
weight relative to the total weight of the mousse.
36. The method according to claim 34, wherein said at least one
propellant is present in a proportion ranging from 1% to 20% by
weight relative to the total weight of the mousse.
37. The method according to claim 28, wherein said cosmetic
composition is in the form of a water-in-oil emulsion comprising a
fatty phase present in an amount ranging from 30% to 50% by weight
relative to the total weight of the composition.
38. The method according to claim 28, wherein said cosmetic
composition is in the form of an oil-in-water emulsion comprising a
fatty phase present in an amount ranging from 5% to 25% by weight
relative to the total weight of the composition.
39. The method according to claim 28, wherein said cosmetic
composition further comprises at least one emulsifier present in an
amount ranging from 1% to 10% by weight relative to the total
weight of the composition.
40. The method according to claim 28, wherein said cosmetic
composition further comprises at least one emulsifier present in an
amount ranging from 1% to 10% by weight relative to the total
weight of the composition.
41. The method according to claim 38, wherein said oil-in-water
emulsion is present in the form of a microemulsion or gel, the said
fatty phase comprising at least one mineral oil.
42. The method according to claim 41, wherein said oil-in-water
emulsion is present in the form of a gel and further wherein said
at least one mineral oil is present in an amount ranging from 15%
to 20% by weight relative to the total weight of the gel
composition.
43. The method according to claim 28, wherein said cosmetic
composition is in the form of a lotion comprising a cosmetic
vehicle chosen from aqueous and aqueous-alcoholic solutions.
44. The method according to claim 28, wherein said cosmetic
composition is in the form of a lacquer comprising a cosmetic
vehicle chosen from alcohols and aqueous-alcoholic solutions.
45. The method according to claim 44, wherein said lacquer further
comprises at least one film-forming resin, at least one plasticizer
and at least one propellant.
46. The method according to claim 45, wherein said at least one
film-forming resin is present in an amount from 3% to 6% by weight
relative to the total weight of the lacquer.
47. The method according to claim 28, wherein said cosmetic
composition further contains at least one conventional ingredient
chosen from softeners, fragrances, plant and animal extracts,
ceramides, silicones, sunscreens, dyes, antimicrobial agents,
vitamins, preserving agents, sequestering agents, and pH
regulators.
48. A method for strengthening keratin fibers comprising applying a
composition to said fibers and optionally rinsing said keratin
fibers, wherein said composition comprises: at least one polyamino
acid of of formula (I): ##STR00020## wherein X is chosen from
--O--, --S-- and --NR5--; R.sub.1 is chosen from: (i) linear and
branched, saturated and unsaturated, C.sub.1-C.sub.40 alkyl groups,
optionally substituted with at least one substituent chosen from a
hydroxyl group and ##STR00021## wherein said alkyl groups are
optionally interrupted with at least one hetero atom, and r' and
r'', which are identical or different, are each chosen from a
hydrogen atom and C.sub.1-C.sub.6 alkyl groups; and ##STR00022##
wherein s is 0 to 4; R.sub.2 is chosen from a hydrogen atom,
C.sub.1-C.sub.8 alkyl groups, a --CH.sub.2C.sub.6H.sub.5 group, a
--CH.sub.2C.sub.6H.sub.5 pOH group, wherein pOH is para-OH, a
--CH.sub.2OH group, a --CHOH--CH.sub.3 group
and-(CH.sub.2).sub.t-NH.sub.2 groups, wherein t is chosen from 3, 4
and 5; R.sub.3 and R.sub.5 which may be identical or different, are
each chosen from a hydrogen atom and C1-C6 alkyl groups; R.sub.4 is
chosen from a hydrogen atom, NH.sub.2, OH, SH, --CHOHCH.sub.3,
--CONH.sub.2, ##STR00023## --C.sub.6H.sub.5 and --C.sub.6H.sub.5
pOH, wherein pOH is para-OH; and n is an average number greater
than 1 such that the molecular weight of the polyamino acid of
formula (I) ranges from 200 to 200,000, wherein the n repeating
units may be identical or different; or a salt of said polyamino
acid, with the proviso that if X is NH, R.sub.2 is H, and R.sub.3
is CH.sub.3, then R.sub.1 is not
C.sub.15H.sub.31--CH(OH)--CH(CH.sub.2OH) and R.sub.1 is not a
C.sub.8-C.sub.24 alkyl group.
49. A method according to claim 48, comprising rinsing and
subsequently shampooing said fibers.
50. A method according to claim 28, wherein said cosmetic
composition further comprises a cosmetically acceptable
vehicle.
51. A method according to claim 28, wherein said keratin fibers are
hair.
52. A method according to claim 28, wherein said cosmetic
composition further comprises at least one surfactant in an amount
ranging from 0.05% to 30% by weight relative to the total weight of
the composition.
54. A method according to claim 28, further comprising rinsing
following said applying.
55. A method according to claim 28, wherein n is an average number
from 7.4 to 14.2, X is --NH--, R.sub.2 is H, R.sub.3 is --CH.sub.3
, and R.sub.1 is ##STR00024##
56. A method according to claim 28, wherein n is an average number
from 7.4 to 14, X is --NH--, R.sub.2 is H, R.sub.3 is --CH.sub.3 ,
and R.sub.1 is ##STR00025##
57. A method according to claim 28, wherein n is an average number
from 7.2 to 12.5, R.sub.1=C.sub.16H.sub.33, X=--NH--, R.sub.2=H,
and R.sub.3=--CH.sub.3.
58. A method according to claim 28, wherein n is an average number
from 7.4 to 13.2, R.sub.1=C.sub.8H.sub.17-CH=CH--C.sub.8H.sub.16,
X=--NH--, R.sub.2=H, and R.sub.3=--CH.sub.3 .
59. A method according to claim 28, wherein n is an average number
of 12, X is --NH--, R.sub.2 is H, R.sub.3 is --CH.sub.3, and
R.sub.1 is ##STR00026##
60. A method according to claim 28, wherein X is --NH--, R.sub.2 is
H, R.sub.3 is --CH.sub.3, n is an average number of 12, and R.sub.1
is ##STR00027##
61. A method according to claim 28, wherein X is --NH--, R.sub.2 is
H, R.sub.3 is --CH.sub.3, n is an average number of 13, and R.sub.1
is ##STR00028##
62. A method according to claim 28, wherein X is --NH--, R.sub.2 is
H, R.sub.3 is --CH.sub.3, n is an average number of 12, and R.sub.1
is ##STR00029## .
63. A method according to claim 28, wherein said at least one
heteroatom is chosen from nitrogen atoms, oxygen atoms, and silicon
atoms.
64. A method according to claim 47, wherein said at least one
heteroatom is chosen from nitrogen atoms, oxygen atoms, and silicon
atoms.
Description
[0001] The present invention relates to the use of polyamino acid
derivatives in a cosmetic composition to strengthen and care for
keratin fibres, in particular the hair.
[0002] The present invention also relates to a "direct" or
"in-situ" treatment process to strengthen and care for keratin
fibres.
[0003] The expression "direct process" means the treatment of the
fibres by applying to them a cosmetic composition containing, in a
cosmetically acceptable vehicle, at least one pre-synthesized
polyamino acid derivative.
[0004] The expression "in-situ process" means the treatment of the
fibres using precursors which generate a polyamino acid derivative
in these fibres.
[0005] Different classes of polyamino acids have been described,
and their use is well known and widely practised, in particular for
their moisturizing properties.
[0006] In this respect, Japanese patent application JP-07/041 467
discloses a class of polyamino acids of high molecular weight
consisting essentially of cysteine, as well as to the process for
preparing these polyamino acids.
[0007] A class of polyamino acids characterized by the presence of
thiol and/or disulphide functions has also been disclosed in
Japanese patent application JP-06/248 072. These polyamino acids
react with the thiol linkages of keratin, thus forming disulphide
bridges, which makes it possible to increase the sheen and
coloration qualities of the hair.
[0008] Another class of polyamino acids has been disclosed in
Japanese patent application JP-04/198 114, these compounds
consisting essentially of amino acids containing neutral and acidic
chains, and are generally used as moisturizing agents.
[0009] Finally, French patent application FR-2 533 209 discloses
amphipathic lipopeptides consisting of a hydrophilic peptide chain
and a hydrophobic chain of 8 to 24 carbon atoms, as well as to
their use as emulsifiers for immiscible media or for producing
liquid crystals.
[0010] After numerous studies carried out on various classes of
polyamino acids, it has been found, surprisingly and unexpectedly,
that one particular class of polyamino acid derivatives has
considerable properties in terms of strengthening keratin fibres,
resulting from the formation of a substantial deposit of
polypeptide material on the surface of the keratin fibres.
[0011] The use of these polyamino acid derivatives in cosmetic hair
compositions moreover makes it possible to improve the hold and
volume of the hair.
[0012] One subject of the present invention is thus the use, in a
cosmetic composition for strengthening keratin fibres, of at least
one polyamino acid derivative of general formula (I) below:
##STR00002##
in which: [0013] X is --O--, --S-- or --NR.sub.3-- [0014] R.sub.1
represents: [0015] (i) a hydrogen atom, and preferably [0016] (ii)
a linear or branched, saturated or unsaturated, C.sub.1-C.sub.40
alkyl radical, optionally substituted with at least one hydroxyl or
a radical
##STR00003##
[0016] and/or optionally interrupted with at least one hetero atom
chosen from N, O or Si, r' and r'', which may be identical or
different, being a hydrogen atom or a C.sub.1-C.sub.6 alkyl
radical,
##STR00004##
s being 0 to 4
##STR00005##
m being 3 to 5,
[0017] R.sub.2 represents a hydrogen atom or a C.sub.1-C.sub.8
alkyl, --CH.sub.2C.sub.6H.sub.5, --CH.sub.2C.sub.6H.sub.5p-OH,
--CHOH-CH.sub.3 or --(CH.sub.2).sub.t-NH.sub.2 radical, t being 3
to 5,
[0018] R.sub.3 represents a hydrogen atom or a C.sub.1-C.sub.6
alkyl radical,
[0019] R.sub.4 represents a hydrogen atom, --NH.sub.2, --OH, --SH,
--CHOHCH.sub.3, --CONH.sub.2,
##STR00006##
--C.sub.6H.sub.5 or --C.sub.6H.sub.5p-OH, and
[0020] n is an average number greater than 1 such that the
molecular weight of the polyamino acid derivative is between 200
and 200,000, the repeating unit being either identical for the same
derivative, or different, R.sub.2 and/or R.sub.3 then taking at
least one of the other meanings given for these radicals,
or of a salt of the said polyamino acid derivative.
[0021] According to one preferred embodiment, the radical R.sub.1
is other than a hydrogen atom.
[0022] The polyamino acids of formula (I) are known in certain
cases and novel in other cases.
[0023] The process for preparing them consists of a
polycondensation reaction between at least one N-carboxyanhydride
or formula:
##STR00007##
in which: R.sub.2 and R.sub.3 have the same meanings as those given
above for formula (I), and a nucleophilic compound of formula
(III):
R.sub.1-XH (III)
in which R.sub.1 and X have the same meanings as those given above
for formula (I).
[0024] The N-carboxyanhydrides of formula (II) are prepared by the
usual methods, by reacting a D and/or L-.alpha.-amino acid with
phosgene in an inert solvent such as dioxane or tetrahydrofuran
(THF).
[0025] The polycondensation reaction is generally carried out at a
temperature of between about 0.degree. C. and 120.degree. C. in an
inert solvent chosen from benzene, toluene, chlorobenzene,
dichloroethane, dimethylacetamide (DMAC), dimethylformamide (DMF),
methyl ethyl ketone (MEK), aliphatic ethers such as ethyl ether,
isopropyl ether and teat-butyl methyl ether, and cyclic ethers such
as tetrahydrofuran and dioxane. However, the reaction solvent can
optionally be water.
[0026] The formation of a more or less pronounced evolution of
CO.sub.2 can be observed from the start of the . reaction.
[0027] After optionally cooling the reaction medium, the solvent is
evaporated off and the polyamino acid derivative obtained is then
dried under vacuum.
[0028] Depending on the purity obtained, a purification step such
as a precipitation or a crystallization of the crude product
obtained can be carried out.
[0029] In the process for preparing the polyamino acid derivative
as described above, the nucleophilic compound acts as an initiator
for the polycondensation reaction.
[0030] According to one preferred embodiment, the molar amount of
the nucleophilic compound of formula (III) is 1/2- 1/3000,
preferably 1/5- 1/2000 per mole of the N-carboxyanhydride of
formula (II).
[0031] Any type of container and valve system for an aerosol foam
is suitable for carrying out the invention according to this
embodiment.
[0032] According to a third embodiment of the compositions
according to the invention, they are in the form of dispersion or
an emulsion of the oil-in-water or water-in-oil type, and more
particularly in the form of a microemulsion or gel.
[0033] The aqueous phase is generally present in a proportion of
between 60% and 90% for the oil-in-water emulsions and between 30%
and 60% for the water-in-oil emulsions, by weight relative to the
total weight of the composition.
[0034] The fatty phase is generally present in a proportion of
between 5% and 25% for the emulsions of oil-in-water type, and
between 30% and 50% for the emulsions of water-in-oil type, by
weight relative to the total weight of the composition.
[0035] The fatty phase consists of at least one cosmetic oil or a
mixture of at least one oil and at least one wax, these being of
mineral, plant, animal or synthetic origin, as described in patent
FR-2 668 927.
[0036] Among the emulsifiers which can be used in the compositions
in the form of an oil-in-water emulsion, mention may be made, inter
alia, of lauryl sulphate, triethanolamine stearate or fatty
alcohols such as stearyl alcohol or cetyl alcohol.
[0037] Among the emulsifiers which can be used in the compositions
in the form of a water-in-oil emulsion, mention may be made, inter
alia, of glycerol esters, ethoxylated alcohols, lanolin, lanolin
alcohol, cholesterol and various sorbitan oleates.
[0038] The emulsifiers are generally present in a proportion of
between 1% and 10% by weight relative to the total weight of the
composition.
[0039] According to this embodiment, the compositions are
preferably transparent microemulsions or gels, and contain an
excess of emulsifier and at least one mineral oil of low
viscosity.
[0040] The mineral oils which can be used in the gel compositions
contain short carbon-based chains and are present in a proportion
of between 15% and 20% by weight relative to the total weight of
the composition.
[0041] Among the emulsifiers for the compositions in gel form which
may be mentioned in particular are polyoxyethylated ether and oleyl
alcohol or its phosphonic ester, polyethoxylated lauryl alcohol,
polyethoxylated oleyl alcohol, oxyethylated cetyl alcohol and
various polyoxythylene glycols of fatty acids.
[0042] The compositions in gel form can also contain a coupling
agent such as 2-ethylhexane-1,3-diol, a polyhydric alcohol such as
sorbitol, a polyethylene glycol, lanolin or lanolin alcohol, as
well as preserving agents.
[0043] According to a fourth embodiment of the compositions
according to the invention, they are in the form of a lotion.
[0044] The vehicle for these lotions is either an aqueous solution
or an aqueous-alcoholic solution containing, in substantially equal
parts, deionized water and an alcohol such as ethanol or
isopropanol.
[0045] The lotions can also contain at least one substance chosen
from an isopropyl ester and a polyalkylene glycol or the oleate
thereof.
[0046] According to a final embodiment of the compositions
according to the invention, they are in the form of a lacquer and
more particularly of an aerosol hair lacquer.
[0047] The cosmetically acceptable vehicle generally used in the
lacquers consists of an alcohol such as ethanol or isopropanol or
an aqueous-alcoholic mixture.
[0048] The lacquers according to this specific embodiment also
contain at least one film-forming resin, at least one plasticizer
and a propellant.
[0049] The film-forming resins used in the lacquers are well known
in the prior art and mention may be made in particular of those
described in patent FR-2 684 874, and they are preferably present
in a proportion of from 3% to 6% by weight relative to the total
weight of the composition.
[0050] Among the preferred plasticizers which may be mentioned in
particular are glycol ethers, benzyl alcohol, triethyl citrate,
1,3-butylene glycol and propylene carbonate, which are present in a
proportion of between X% and Y% by weight relative to the total
weight of the composition.
[0051] The propellant for the lacquers can be chosen from at least
one of the agents listed above for preparing compositions in the
form of a mousse.
[0052] The lacquers according to this embodiment can also contain
other conventional ingredients, such as corrosion inhibitors,
softeners, fragrances, silicones, sunscreens, dyes, preserving
agents, anti-foaming agents and vitamins.
[0053] After introducing the composition or "fluid" into a suitable
container, the container is fitted with a suitable valve and
diffusion system.
[0054] Among the valves which can be used, mention may be made in
particular of those described in patent FR-2 382 637.
[0055] A subject of the present invention is also a repairing care
and treatment process for keratin fibres, referred to hereinabove
as a "direct" treatment process, this process consisting in
applying to the keratin fibres a composition as defined above
containing at least one polyamino acid derivative, and in leaving
the composition to act on the fibres, optionally followed by
rinsing the keratin fibres.
[0056] According to one particularly preferred embodiment of the
repairing care and treatment process of the keratin fibres,
referred to hereinabove as the "in-situ" treatment process, the
polyamino acid derivative of formula (I) is formed "in situ", i.e.
directly on the keratin fibres which are subjected to the
treatment, with the aid of precursors which generate the polyamino
acid derivative.
[0057] These precursors are, on the one hand, an N-carboxyanhydride
of formula (II) and, on the other hand, a nucleophilic compound of
formula (III) which, to carry out the treatment, are in the form of
a packaging in two Parts.
[0058] The first part contains at least one N-carboxyanhydride of
formula (II) in solid form or diluted in a cosmetically acceptable
vehicle, and the second part contains a nucleophilic compound of
formula (III), in solid form or diluted in a cosmetically.
acceptable vehicle.
[0059] The cosmetically acceptable vehicle for the
N-carboxyanhydride of formula (II) is an organic solvent, water or
a mixture thereof. The cosmetically acceptable vehicle for the
nucleophilic compound of formula (III) is preferably water.
[0060] The "in-situ" treatment process consists, in a first stage,
in applying to the hair, which has optionally been moistened
beforehand, the first part of the packaging, after optional
dilution using a liquid medium, and then, in a second stage, in
applying the second part of the packaging, also after optional
dilution, in particular water-based dilution.
[0061] According to this process, if so desired, the two parts can
be premixed and the solution obtained can be applied directly to
the hair.
[0062] The hair is then rubbed, which brings about, in aqueous
medium, the polycondensation of the precursors as a polyamino acid
derivative. The polycondensation is generally complete after a
period of about 2 to 30 minutes.
[0063] After this period of time, the hair is rinsed and optionally
shampooed.
[0064] Examples of the preparation of the polyamino acid
derivatives and examples of cosmetic compositions and of a hair
treatment process will now be given by way of illustration.
EXAMPLES
Example 1
[0065] Preparation of the Polyamino Acid of Formula (I) in
Which
##STR00008##
[0066] 46 g (0.4 mol) of sarcosine N-carboxyanhydride are suspended
in 250 cm.sup.3 of toluene, under a nitrogen atmosphere, in a
1-litre reactor equipped with a condenser, a thermometer, a
nitrogen inlet, an addition funnel and a stirrer. A suspension of
8.2 g (0.027 mol) of (D/L, erythro-threo)
2-aminooctadecane-1,3-diol in 250 cm.sup.3 of toluene is then added
portionwise. After the end of the addition, the reaction mixture is
maintained at 80.degree. C. for about 3 hours. It is then allowed
to cool to room temperature and 200 cm.sup.3 of ethanol (98.degree.
C.) are added to dissolve the medium.
[0067] After evaporating off the solvents under reduced pressure
and drying under vacuum, 34.5 g of a brown-coloured powder are
obtained.
[0068] The "n" index was determined by NMR.
[0069] According to the same procedure as above, by varying the
proportion of (DL)-2-aminooctadecane-1,3-diol, polyamino acid
derivatives having the same structure but having the following "n"
indices were obtained:
Example 1(a):n=9.8 Example 1(b):n=7.6
Example 2
[0070] Preparation of the Polyamino Acid of Formula (I) in
Which
##STR00009##
[0071] 46 g (0.4 mol) of sarcosine N-carboxyanhydride are suspended
in 500 cm.sup.3 of toluene in a 1-litre reactor equipped with a
condenser, a thermometer, a nitrogen inlet, an addition funnel and
a stirrer. 8.1 g (0.027 mol) of 2-octyldodecylamine are then added
dropwise. After the end of the addition, the mixture is maintained
at 80.degree. C. for about 2 hours. It is then allowed to cool to
room temperature, followed by addition of 50 cm.sup.3 of ethanol
(95.degree. C.). After evaporating off the solvents under reduced
pressure and drying under vacuum, 36.7 g of a brown-coloured powder
are obtained.
[0072] The "n" index was determined by NMR.
[0073] According to the same procedure as above, but by varying the
proportion of 2-octyldodecylamine, polyamino acid derivatives
having the same structure but having the following "n" indices were
obtained:
Example 2(a):n=9.6 Example 2(b):n=7.4
Example 3
[0074] Preparation of the Polyamino Acid of Formula (I) in Which
R.sub.1=C.sub.16H.sub.33, X=--NN--, R.sub.2=H, R.sub.3=--CH.sub.3
and n=7.2.
[0075] This polyamino acid is obtained according to the same
procedure as that described in Example 2, but by reacting 12 g
(0.05 mol) of hexadecylamine with the sarcosine
N-carboxyanhydride.
[0076] After evaporating off the solvents and drying under vacuum,
40 g of a powder are obtained.
[0077] By varying the proportion of hexadecylamine, polyamino acid
derivatives having the same structure but having the following "n"
indices were obtained:
Example 3(a):n=9.2 Example 3(b):n=12.5
Example 4
[0078] Preparation of a Polyamino Acid Derivative of Formula (I) in
Which R.sub.1=C.sub.8H.sub.17-CH=CH-C.sub.8H.sub.16, X=--NH--,
R.sub.2=H, R.sub.3=-CH.sub.3 and n=7.4.
[0079] This polyamino acid is obtained according to the same
procedure as that described in Example 2, but by reacting 13 g
(0.05 mol) of oleylamine with the sarcosine N-carboxyanhydride.
[0080] After evaporating off the solvents and drying under vacuum,
42 g of a powder are obtained.
[0081] By varying the proportion of oleylamine, polyamino acid
derivatives having the same structure but having the following "n"
indices were obtained:
Example 4(a):n=10.5 Example 4(b):n=13.2
Example 5
Preparation of the Polyamino Acid of Formula (I) in Which
##STR00010##
[0083] 10 g (0.08 mol) of sarcosine N-carboxyanhydride are placed
in a 500 ml conical flask with stirring, followed by addition of
100 cm.sup.3 of distilled water (pH 6.7) and addition of 1 g (0.006
mol) of lysine in a single portion.
[0084] A considerable evolution of CO.sub.2 is produced and
stirring of the mixture is continued for about 30 minutes at room
temperature. After evaporating off the water under reduced pressure
and drying under vacuum, 6.7 g of a brown-coloured powder are
obtained.
[0085] The "n" index was determined by NMR.
[0086] According to the same procedure as above, but varying the
proportion of lysine, polyamino acid derivatives having the same
structure but having the following theoretical "n" indices were
obtained:
Example 5(a):n=50 Example 5(b):n=25 Example 5(c):n=6 Example
5(d):n=3
Example 6
Preparation of the Polyamino Acid of Formula (I) in Which
##STR00011##
[0087] and n=13 (theoretical index).
[0088] This polyamino acid is obtained according to the same
procedure as that described in Example 5, but replacing the lysine
with the corresponding molar amount of cysteine.
Example 7
Preparation of the Polyamino Acid of Formula (I) in Which
##STR00012##
[0089] and n=12 (theoretical index).
[0090] This polyamino acid is obtained according to the same
procedure as that described in Example 5, but replacing the lysine
with the corresponding molar amount of arginine.
Example 8
Preparation of the Polyamino Acid of Formula (I) in Which
##STR00013##
[0091] and n=12 (theoretical index).
[0092] This polyamino acid is obtained according to the same
procedure as that described in Example 5, but replacing the lysine
with the corresponding molar amount of histidine.
Example 9
Preparation of the Polyamino Acid of Formula (I) in Which
##STR00014##
[0093] and n=13 (theoretical index).
[0094] This polyamino acid is obtained according to the same
procedure as that described in Example 5, but replacing the lysine
with the corresponding molar amount of glutamine.
Example 10
[0095] Preparation of the polyamino acid of formula (I) in
Which
##STR00015##
and n=12 (theoretical index).
[0096] This polyamino acid is obtained according to the same
procedure as that described in Example 5, but replacing the lysine
with the corresponding molar amount of glucamine.
EXAMPLES OF COSMETIC COMPOSITIONS
[0097] The following formulations for hair care and hair treatment
were prepared:
Example 11
Shampoo
TABLE-US-00001 [0098] Sodium lauryl ether sulphate (28% A.M.) 75 g
Coconut acid monoisopropanolamide sold 1 g by the company Aibright
& Wilson under the name "Empilan CIS.RTM." Polyamino acid of
Example 5 1 g Water q.s 100 g
[0099] The shampoo thus formulated is of clear appearance.
Example 12
Rinse-Out Hair Conditioner
TABLE-US-00002 [0100] 1-methyl-2-tallow-3-sulphamidoethyl- 2 g A.M.
imidazolium methosulphate/propene glycol (75/25) sold by the
company Witco under the name "Rewoquat W752G.RTM." Polyamino acid
of Example 5 0.5 g Oxyethylenated mixture of cetyl alcohol 3 g and
cetylstearyl alcohol Preserving agent, fragrance, q.s. Spontaneous
pH of 5.2 Water q.s 100 g
Example 13
Shampoo
TABLE-US-00003 [0101] Sodium lauryl ether sulphate (28% A.M.) 60 g
Cocoyl betaine 9 g Polyamino acid of Example 1 0.5 g Preserving
agent, fragrance q.s. HCl q.s. pH 6 Water q.s. 100 g
[0102] The shampoo thus formulated is opalescent.
Example 14
Rinse-Out Disentangling Lotion
TABLE-US-00004 [0103] Behenyltrimethylammonim chloride at 0.5 g
A.M. 80% in a water/isopropanol mixture (15/85) sold by the company
Toho under the name "Catinal DC 50.RTM." Polyamino acid of Example
4 0.1 g Preserving agent, fragrance q.s. NaOH q.s. pH 5.5 Water q.s
100 g
[0104] The examples which follow of strengthening treatment were
carried out on the head ("in situ").
Example 15
Hair Treatment Process Using a Conditioner In Two Parts
[0105] A first conditioner containing a sarcosine
N-carboxyanhydride solution diluted to 10% either in Soketal.RTM.
(D,L-.alpha.,.beta.-isopropylidene glycerol) or in dimethyl ether
isosorbide, is first applied to hair which has been moistened
beforehand. The solution thus applied should impregnate the hair
entirely. Next, a second conditioner containing an L-lysine
solution diluted to 4% in water is then applied. After leaving to
act for 15 minutes, the hair is rinsed with warm water, shampooed
and finally dried.
Example 16
Hair Treatment Process Using a Solid Conditioner in Two Parts
[0106] Sarcosine N-carboxyanhydride conditioned in solid form is
first applied to hair which has been moistened beforehand and is
then massaged for about 5 minutes. Next, an L-lysine solution
diluted to 4% in water, packaged separately, is then added to the
hair.
[0107] After leaving to act for about 15 minutes, the hair is
rinsed with warm water, washed with a shampoo and dried.
[0108] The hair treated according to Example 15 or 16 shows a
visible improvement in hold and volume.
COMPARATIVE TESTS
Study of the Keratin-Fibre-Strengthening Properties
[0109] The properties of strengthening natural hair and bleached
hair were evaluated after treatment according to the "in-situ"
process.
[0110] Locks of 0.6 g and of 15 cm of natural dark-chestnut hair,
on the one hand, and of bleached hair, on the other hand, were
first immersed in a phosphate buffer at 37.degree. C., then rinsed
with water and then shampooed and rinsed again.
[0111] One portion of the locks obtained serves as a control and
the others were then treated using a solution prepared at the time
of use by mixing 1 g of sarcosine N-carboxyanhydride (sarcosine
NCA) and 0.1 g of lysine in a phosphate buffer at 37.degree. C.
After a period of about 30 minutes, in the course of which the
polycondensation reaction takes place, the locks were then rinsed
with water, after which they were shampooed and rinsed again. The
strengthening of the locks thus treated was quantified with the aid
of the flexibility pendulum test. This flexibility pendulum test
consists in measuring the number of oscillations of a pendulum
having a ballast weight of 47 g which curves a sample of 39 hairs
10 mm in length. The hair-strengthening characteristics are
inversely proportional to the number of oscillations of the
pendulum. Specifically, any increase in the strengthening of the
hair is reflected by a decrease in the number of oscillations of
the pendulum.
[0112] The measurements of the number of oscillations on three
samples of locks of natural and bleached hair, at a temperature of
25.degree. C., and at a relative humidity of 45%, are given in
Table 1 below:
TABLE-US-00005 TABLE 1 Natural Standard Bleached Standard Number of
oscillations hair error hair error Control phosphate 159 2 130 2
buffer Sarcosine NCA/lysine 148 2 125 1 (Test 1) Sarcosine
NCA/lysine 149 2 130 1 (Test 2) Sarcosine NCA/lysine 150 1 125 1
(Test 3) % variation -6 p = 0.000l -3 p = 0.04
[0113] The difference observed in the number of oscillations
between the natural hair and the bleached hair, before any
treatment, can be explained essentially by the fact that bleaching
gives rise to a large increase in the rigidity of the hair.
[0114] The results of Table 1 above show a reproducible decrease in
the number of oscillations of the pendulum, of less than 6% for the
natural hair, and of less than 3% for the bleached hair.
[0115] The "in-situ" treatment thus gives, after the
polycondensation reaction, a significant increase in the intrinsic
rigidity properties of natural and bleached hair. These
characteristics are conserved and are always visible, even after
the locks have been shampooed and then rinsed.
Quantification of the Deposition of Polylysine-Sarcosine on Keratin
Fibres
[0116] The deposition of polylysine-sarcosine was determined by
assaying the amount of residual sarcosine on the surface of locks
of natural or bleached hair after "direct" treatment and after
"in-situ" treatment.
[0117] The quantification of the deposition of sarcosine was
carried out after rinsing the treated locks, and after rinsing and
shampooing the treated locks.
[0118] The locks of hair after these operations were subjected to
an acid hydrolysis, and the amount of residual sarcosine was
measured using a Hitachi L8500A amino acid autoanalyser. The
amounts of sarcosine found on the surface of the samples of natural
and bleached hair are given in Table 2 below. These amounts are
expressed in grams of sarcosine present on the hair per 100 grams
of hair.
TABLE-US-00006 TABLE 2 TREAT- MENTS As g of "In-situ" "Direct"
After After sarcosine treat- treat- rins- shampoo- per 100 g ment
ment ing ing of hair Control + 0 NATURAL + + + 0.26 HAIR + + 0.32 +
+ + 0.16 + + 0.25 Control + 0 BLEACHED + + + 0.38 HAIR + + 0.67 + +
+ 0.36 + + 0.55
[0119] From Table 2 above, it may be observed that there is an
appreciable sarcosine deposit after treatment and rinsing. This
sarcosine deposit moreover remains in a satisfactory proportion
after subsequent shampooing.
* * * * *