Toilet – Methods – Hair treatment by application of specific chemical composition
Reexamination Certificate
2000-01-06
2001-06-05
Dawson, Robert (Department: 1712)
Toilet
Methods
Hair treatment by application of specific chemical composition
C528S028000, C528S027000, C556S413000, C556S450000, C556S425000, C424S070200, C424S070510, C424S070120, C424S070600, C132S204000, C132S208000, C008S405000, C524S800000, C524S081000
Reexamination Certificate
active
06240929
ABSTRACT:
The present invention relates to novel heterocyclic polyquaternary ammonium silicone polymers, to cosmetic compositions using them and to processes for treating keratin fibres, and in particular the hair using these polymers.
It has already been proposed to use polyquaternary polysiloxane polymers in order to improve the disentangling of the hair. Such compositions are described in particular in French patent No. 2,535,730 by the Applicant.
Document U.S. Pat. No. 4,833,225 describes polyquaternary polysiloxane polymers which are resistant to removal by washing and allow easy styling.
Cationic polymers have a great affinity for keratin fibres, such as the hair, on account of the interaction of the cationic groups with the anionic groups of the hair.
These polymers become deposited on the hair all the more easily the more sensitized this hair, and their affinity for the hair is often such that they are resistant to removal by shampooing or brushing.
It is found, however, that although the use of such cationic polymers has many advantages, since they facilitate disentangling of the hair and they give the hair liveliness and a shiny appearance, on account of their affinity for keratin, these polymers have a tendency to accumulate on the hair after repeated applications.
Moreover, cationic polymers containing quaternary groups often have the drawback of being incompatible with anionic surfactants, which reduces the possibilities for use and imposes their use in two-stage treatments, before or after shampooing.
The Applicant has discovered that certain polyquaternary ammonium silicone polymers, which do not have the abovementioned drawbacks, containing at least some unsaturated quaternary heterocycles, are particularly advantageous for treating keratin fibres, and in particular human keratin fibres such as the hair.
The Applicant has discovered, in particular, that the use of these polymers allows keratin fibres, and in particular human keratin fibres such as the hair, to be protected both against attack due, in particular, to sunlight, to bad weather and to perspiration, and against attack resulting from treatment of keratin fibres, and in particular human keratin fibres such as the hair, such as, for example, bleaching, permanent-waving or dyeing operations.
It has been found that keratin fibres have a tendency to become brittle when they are subjected to these treatments; keratin fibres, and in particular human keratin fibres such as the hair, become dry, dull, coarse and difficult to disentangle and to style.
The protective agents of the invention are used in particular in any cosmetic process which includes at least one step during which the keratin fibres are liable to be exposed to various attacking factors, and thus allow the abovementioned drawbacks to be avoided.
These protective agents can be applied to the keratin fibres during, prior to or subsequent to this step during which the keratin fibres are subjected to attacking factors.
Preferably, the protective agents of the present invention are used in a process during which at least one application of an alkaline composition onto the keratin fibres takes place.
A subject of the invention is thus novel heterocyclic polyquaternary silicone polymers.
A subject of the invention is also the use of these novel heterocyclic polyquaternary silicone polymers as agents for protecting keratin fibres.
A subject of the invention is also cosmetic compositions using them, and in particular compositions intended for permanently shaping keratin fibres, bleaching compositions and dye compositions.
A subject of the invention is also processes for treating keratin fibres, and in particular human keratin fibres such as the hair, using these compositions.
Other subjects of the present application will become apparent on reading the description and the examples which follow.
The polymers of the present invention contain at least some repeating units of formula (I):
in which:
A
1
⊕
and A
2
⊕
; which may be identical or different, denote:
a) a quaternary unsaturated heterocycle of formula (II):
in which
E, G, L and J, which may be identical or is different, denote a carbon, oxygen, sulphur or nitrogen atom, at least one denoting a nitrogen atom;
E, G, L and J can be substituted, when one or more of these atoms denote a carbon atom, with one or more halogen atoms, hydroxyl, nitro, cyano, sulphydryl or carboxyl groups, alkyl, monohydroxyalkyl, polyhydroxyalkyl, thioalkyl, cyanoalkyl, alkoxy, acyl or acetyloxy groups, or substituted or unsubstituted cycloalkyl groups or substituted or unsubstituted alkylaryl groups, or with one or more groups —NHR
N
in which, R
N
denotes an acetyl or ureido group;
when E, G, L or J denote a third nitrogen atom, this can be substituted with a hydrogen, an alkyl, monohydroxyalkyl, polyhydroxyalkyl or substituted or unsubstituted aryl radical or a substituted or unsubstituted alkylaryl radical;
the substituents of two of the atoms E, G, L and J can also form, together with the atoms to which they are attached, a substituted or unsubstituted 5- to 7-membered aromatic ring; or
b) a quaternary ammonium of formula (III)
in which:
R
s
and R
6
, which may be identical or different; denote a carbdixyl group, an alkyl, polyhydroxyalkyl, thioalkyl, cyanoalkyl, alkoxy, acyl or acetyloxy group, a substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted alkylaryl group or a group —NHR
N
in which R
N
, denotes an acetyl or ureido group;
R
5
and R
6
can also form, together with the nitrogen atom to which they are attached, a saturated ring of 5 to 7 carbon members;
and at least one of the groups A
1
⊕
and A
2
⊕
denotes a quaternary unsaturated heterocycle of formula (II);
p denotes an integer or fraction from 0 to 50 and preferably from 0 to 10; p can represent a defined number or an average statistical value;
B
1
denotes an &agr;, &ohgr;-bis(alkyl)polysiloxane group or a linear or branched, saturated or unsaturated hydrocarbon-based chain containing upto 6 consecutive carbon atoms, which can contain one or more hydroxyl groups and can be interrupted by one or more oxygen atoms and/or several aromatic rings;
B
2
denotes a linear or branched, saturated or unsaturated hydrocarbon-based chain containing upto 6 consecutive carbon atoms, which can contain one or more hydroxyl groups and can be interrupted by one or more oxygen atoms and/or one or more aromatic rings;
R
1
, R
2
, R
3
and R
4
, which may be identical or different, denote a C
1
-C
6
alkyl radical or a phenyl radical;
X
⊖
denotes an anion derived from an inorganic or organic acid.
In the context of the present invention:
The halogen atoms preferably denote a fluorine, chlorine, bromine or iodine atom.
The alkyl, monohydroxyalkyl and polyhydroxyalkyl radicals and the hydrocarbon-based gruops can be linear or branched.
The alkyl groups denote, in particular, groups containing from 1 to 20 carbon atoms, such as, for example, methyl, ethyl, propyl, isopropyl, n-propyl, butyl, n-butyl, tert-butyl, pentyl, n-pentyl, isopentyl, n-hexyl, isohexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and pentadecyl groups. Preferably, the alkyl groups denote a group containing from 1 to 6 carbon atoms.
Among the hydrocarbon-based groups, mention may be made of polymethylene groups containing from 1 to 20 carbon atoms.
Preferably, the hydrocarbon-based groups denote polymethylene groups containing from 2 to 8 carbon atoms.
The hydrocarbon-based groups can contain, attached to or inserted in the main chain, one or more aromatic rings, one or more oxygen, sulphur or nitrogen atoms, or one or more —SO—, —SO
2
—, —SO
3
H, amino, alkylamino, hydroxyl, quaternary ammonium or ureido groups.
Among the monohydroxyalkyl groups, mention may be made in particular of hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl groups.
Among the polyhydroxyalkyl radicals, mention may be made, for example, of dihydroxyethyl, dihydroxypropyl, trihydroxypropyl and dihydroxybutyl radicals.
The thioalkyl radicals
Lagrange Alain
Richard Herve
Dawson Robert
Finnegan Henderson Farabow Garrett & Dunner
L'Oreal (S.A.)
Peng Kuo-Liang
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