Drug – bio-affecting and body treating compositions – Live hair or scalp treating compositions – Polymer containing
Reexamination Certificate
2000-02-23
2004-08-03
Sergent, Rabon (Department: 1711)
Drug, bio-affecting and body treating compositions
Live hair or scalp treating compositions
Polymer containing
C424S070170, C424S401000, C524S591000, C524S839000, C524S840000, C528S071000, C528S080000, C528S083000
Reexamination Certificate
active
06770271
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a new family of polyester polyurethanes film-forming resins, to a process for preparing them, to pseudolatices produced using said polyester polyurethanes resins and also to cosmetic compositions containing said pseudolatices.
BACKGROUND
It is common practice to use polyurethanes as film-forming resin in many cosmetic formulations, and in particular in different make-up products such as nail varnishes, mascaras and eyeliners. To be satisfactory, the resin must possess not only good film-forming properties, but also good staying properties, that is to say must be difficult to remove from its support by simply washing with water or by means of detergents.
In Patent Application EP 418,469, nail varnish compositions containing aqueous dispersions of aliphatic polyurethanes as film-forming resin have been described.
In Patent Application EP 391, 22, nail varnishes containing an aqueous dispersion of a polyurethane and/or of a polyurethane copolymer have also been described.
The use of these resins does not, however, enable compositions possessing good cosmetic properties to be procured, as a result, in particular, of a lack of staying power.
SUMMARY OF THE INVENTION
The present invention relates to polyurethanes and a process for preparing them. These polyester polyurethanes contain units corresponding to the following formulae (I) and (II):
The polyester polyurethanes according to the present invention form pseudolatices and may be utilized as film-forming resin in cosmetic compositions.
It has now been found that, surprisingly and unexpectedly, a new family of polyester polyurethanes not only possess good film-forming properties, but also enable films possessing both great rigidity and excellent resistance to removal by water and detergents to be obtained.
It has been possible to obtain these excellent properties as a result of the particular choice of &agr;, &ohgr;-dihydroxy polyester participating in the synthesis of the polyester polyurethanes according to the invention.
The polyester polyurethanes according to the invention make it possible to prepare pseudolatices which also have very good staying power and which, furthermore, are especially stable without the use of additional surfactants, in as much as they contain, in addition, ionic functions.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The subject of the present invention is, as a new industrial product, a polyester polyurethane containing units corresponding to the following formulae (I) and (II):
in which:
R represents an alkylene or cycloalkylene radical or a bivalent aromatic radical having from 6 to 15 carbon atoms,
n represents an integer such that the molecular weight of the recurring unit is between 400 and 5,000,
R
1
represents a bivalent radical chosen from the group consisting of;
(i) &Parenopenst;CH
2
&Parenclosest;
m
, m being an integer between 2 and 12, and
(ii)
the movable bond being in the ortho, meta or para position,
R2 represents a bivalent radical chosen from the group consisting of:
R
3
representing a hydrogen atom or a branched alkyl radical having from 1 to 3 carbon atoms,
R
4
representing a hydrogen atom or a linear or branched alkyl radical having from 1 to 4 carbon atoms,
R
5
representing a linear or branched alkyl radical having from 1 to 4 carbon atoms, and
p being 0 or 1,
in which:
R is as defined above for the units of formula (I),
A represents an alkylene radical having from 2 to 20 carbon atoms, substituted with a carboxylic or sulphonic acid function, in salified or unsalified form, or interrupted by a tertiary nitrogen atom, the mole ratio between the units (II) and (I) being between 1:1 and 10:1, and preferably between 1:1 and 5:1.
The bivalent radical R of the unit of formula (I) is preferably chosen from the group consisting of hexamethylene, 4,4′-biphenylenemethane, 2,4-and/or 2,6-tolylene, 1,5-naphthylene, p-phenylene and 4,4′-methyl-enebis (cyclohexyl) radicals and the bivalent radical derived from isophorone.
The bivalent radical A of the unit of formula (II) is preferably chosen from the group consisting of:
R
6
representing a linear or branched alkyl radical having from 1 to 3 carbon atoms,
Y representing a carboxylic acid or sulphonic acid group or a salt thereof, and
t and q, which may be identical or different, representing an integer between 1 and 5,
R
7
representing a linear or branched alkyl radical having from 1 to 4 carbon atoms, and
r and s, which may he identical or different, representing an integer between 1 and 10.
The polyester polyurethanes according to the invention can, in addition, contain units corresponding to the following formula (III):
in which:
R is as defined above for the units of formula (I),
B and B′, which may be identical or different, represent —O— or —NH—, it not being possible for B and B′ simultaneously to represent —O—, and
X represents an alkylene or cycloalkylene radical having from 2 to 12 carbon atoms or a hivalent aromatic radical having from 6 to 12 carbon atoms,
the said unit being present in a proportion such that the mole ratio of the sum of the units of formulae (II) and (III) to the units of formula (I) is an integer between 1 and 10, and preferably between 1 and 5.
The molecular weight of the polyester polyurethanes according to the invention, measured by steric exclusion chromatography, is generally between 4,000 and 500,000, and preferably between 6,000 and 200,000.
The subject of the present invention is also the process for preparing said polyester polyurethanes. This process consists in reacting, in an organic solvent, an ∝, w-dihydroxy polyester corresponding to the following formula (IV):
in which:
R
1
, R
2
and n are as defined above for the units of formula (I),
with an excess of a diisocyanate corresponding to the following formula (V):
O═C═N—R—N═C═O (V)
in which R is as defined above for the units of formula (I),
and then in coupling the chains of the polyester polyurethane obtained above with a diol corresponding to the following formula (VI):
HO—A—OH (VI)
in which:
A is as defined above for the units of formula (II),
at a temperature of between 40 and 100° C. in the presence of a tin salt as catalyst.
The organic solvent used in the process according to the invention is preferably chosen from the group consisting of acetone, methyl ethyl ketone, tetrahydrofuran and 1,2-dichloroethane, these solvents being inert with respect to isocyanate groups.
The tin salt is preferably chosen from tin 2-ethylhexanoate and dibutyltin dilaurate.
The &agr;,&ohgr;-dihydroxy polyester of formula (IV) used as starting material in the synthesis of the polyester polyurethanes according to the invention preferably has a molecular weight of between 400 and 5,000.
Among especially preferred &agr;,&ohgr;-dihydroxy polyesters of formula (IV), there may be mentioned that in which R
2
represents a bivalent radical of formula:
and R
1
represents —(CH
2
)
3
— or a p-phenylene radical.
The diisocyanate of formula (V) used in the process according to the invention is preferably chosen from the group consisting of diphenylmethane 4,4′-diisocyanate and dicyclqhexylmethane 4,4′-diisocyanate (or dicyclohexylmethylene 4,4′-diisocyanate).
The diol of formula (VI) used in the process according to invention is preferably chosen from the group consisting of dimethylolpropionic acid and N-methyldiethanolamine.
According to a particular embodiment of the process according to the invention, a coupler corresponding to the following formula (VII):
H—B—X—B′—H (VII)
in which:
B, B′ and X are as defined above for the units of formula (III), is reacted in addition.
Preferably, the coupler is chosen from the group consisting of 1,3-diaminopropane and ethanolamine.
The polyester polyurethane obtained according to the above process is in non crosslinked form and can optionally be purified, for example by precipitation in a non-polar solvent such as cyclohexane.
The subject of t
De La Poterie Valérie
Lion Bertrand
Mondet Jean
Mougin Nathalie
Piot Bertrand
L'Oreal
Oliff & Berridg,e PLC
Sergent Rabon
LandOfFree
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