Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
2000-09-21
2002-07-09
Hartley, Michael G. (Department: 1617)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C528S073000, C528S350000, C548S312700, C510S126000
Reexamination Certificate
active
06416770
ABSTRACT:
This application is a 371 of PCT/FR99/00085 submitted Jan. 18, 1999.
The present invention relates to the use as protective agent for keratinous fibres of poly(heterocyclic quaternary ammonium) polymers, to cosmetic compositions employing them and to hair treatment processes in which these polymers are used.
Provision has already been made to use polymers comprising quaternary ammonium groups as hair conditioning agents. Such compositions are disclosed in particular in the French patents of the Applicant Company Nos. 2,270,846, 2,307,271 and 2,413,907.
Cationic polymers exhibit a high affinity for keratinous fibres, such as the hair, due to the interaction of the cationic groups with the anionic groups of the individual hair.
The deposition of these polymers on the hair becomes easier as the latter becomes more sensitized and their affinity for the hair is often such that they withstand removal by shampooing or by brushing.
However, it has been found that, while the use of such cationic polymers exhibits numerous advantages in so far as they facilitate disentangling of the hair and as they confer qualities of liveliness and a glossy appearance thereon, due to their affinity for keratin, these polymers have a tendency to accumulate on the hair following repeated applications.
Cationic polymers comprising quaternary groups furthermore often exhibit the disadvantage of not being very compatible with anionic surface-active agents, which reduces the possibilities of use and requires them to be used in two-step treatments, before or after shampooing.
The Applicant Company has discovered that some poly(quaternary ammonium) polymers, which do not exhibit the abovementioned disadvantages, comprising at least unsaturated quaternary heterocycles, are particularly advantageous in hair treatment.
The Applicant Company has discovered in particular that the use of these polymers makes it possible to protect the hair both with regard to attacks due in particular to the sun, to bad weather or to perspiration and with regard to those resulting from hair treatment, such as, for example, bleachings, permanent waves or dyeings.
It has been found that keratinous fibres have a tendency to be rendered brittle when they are subjected to these treatments; the hair becomes dry, dull and rough, and difficult to disentangle and to style.
The protective agents of the invention are of use in particular in any cosmetic process comprising at least one stage during which the keratinous fibres are liable to be exposed to various attacks and thus make it possible to avoid the abovementioned disadvantages.
These protective agents can be applied to the keratinous fibres during, prior to or subsequent to this stage during which the keratinous fibres are subjected to attacks.
The protective agents of the present invention are preferably used in a process during which at least one application of an alkaline composition to the keratinous fibres takes place.
A subject-matter of the invention is thus the use as protective agent of heterocyclic polyquaternary polymers.
Another subject-matter of the invention is cosmetic compositions employing them and in particular compositions intended for permanent shaping of keratinous fibres, bleaching compositions and dyeing compositions, preferably oxidation dyeing compositions.
A further subject-matter of the invention is a hair treatment process employing these compositions.
Other subject-matters of the present application will emerge on reading the description and examples which follow.
The polymers used as protective agent for keratinous fibres are basically composed of repeat units of formula (I):
in which:
A
1
&rgr;
and A
2
&rgr;
, which are identical or different, denote:
a) an unsaturated quaternary heterocycle of formula (II):
in which:
E, G, L and J, which are identical or 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, by one or more halogen atoms, hydroxyl, nitro, cyano, mercapto or carboxyl groups, an alkyl, monohydroxyalkyl, polyhydroxyalkyl, thioalkyl, cyanoalkyl, alkoxy, acyl or acetyloxy group, a substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted alkylaryl group, or —NHR
N
groups in which R
N
denotes an acetyl or ureido group.
When E, G, L or J denotes a third nitrogen atom, the latter can be substituted by a hydrogen or an alkyl, monohydroxyalkyl, polyhydroxyalkyl, substituted or unsubstituted aryl or substituted or unsubstituted alkylaryl radical.
The substituents of two of the E, G, L and J atoms can also form, jointly 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
1
and R
2
, which are identical or different, denote a carboxyl 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 an —NHR
N
group in which R
N
denotes an acetyl or ureido group;
R
1
and R
2
can also form, jointly with the nitrogen atom to which they are attached, a saturated 5- to 7-membered carbonaceous ring;
and in which at least one of the A
1
&rgr;
or A
2
&rgr;
groups denotes an unsaturated quaternary heterocycle of formula (II).
B
1
and B
2
, which are identical or different, denote a hydrocarbonaceous group which can comprise, bonded to or inserted in the main chain, one or more substituted or unsubstituted 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.
X
&sgr;
represents an anion derived from an organic or inorganic acid.
The polymers of the present invention have a mass-average molecular weight preferably of between 1000 and 20,000, measured by gel permeation chromatography using polyethylene glycol as reference.
In the context of the present invention:
The halogen atoms preferably denote a fluorine, chlorine, bromine or iodine atom.
The alkyl, monohydroxyalkyl or polyhydroxyalkyl radicals and the hydrocarbonaceous groups can be linear or branched.
The alkyl groups denote in particular groups of 1 to 20 carbon atoms, such as, for example, the 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. The alkyl groups preferably denote a group of 1 to 6 carbon atoms.
Mention may be made, among the hydrocarbonaceous groups, of polymethylene groups of 1 to 20 carbon atoms.
The hydrocarbonaceous groups preferably denote polymethylene groups of 2 to 8 carbon atoms.
The hydrocarbonaceous groups can comprise, bonded 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.
Mention may in particular be made, among the monohydroxyalkyl groups, of hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl groups.
Mention may be made, among the Apolyhydroxyalkyl radicals, of, for example, dihydroxyethyl, dihydroxypropyl, trihydroxypropyl and dihydroxybutyl radicals.
The thioalkyl radicals denote an —R—SH group, R representing an alkyl group as defined above.
The cyanoalkyl radicals denote an —R—C═N group, R representing an alkyl group as defined above.
The alkoxy groups denote an —O—R group, R representing an alkyl group as defined above.
The acyl groups denote an —OC—R group, R representing an alkyl group as defined above.
The acetyloxy groups denote an —O—CO—R group, R representing an alkyl group as defined above.
Mention may in particular be made, among the cycloalkyl radicals, of cyclohexyl and cyclopentyl.
Mention may in particular be made, among the aryl radicals, of phenyl or naphthyl group
Lagrange Alain
Leduc Madeleine
Richard Herve
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
Hartley Michael G.
L'Oreal (S.A.)
Willis Michael A.
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