WO2005100359A1

WO2005100359A1 - Composition containing a monomer compound exhibiting an optical property, method making use of said composition, a monomer compound and polymer containing said compound

Info

Publication number: WO2005100359A1
Application number: PCT/FR2005/000457
Authority: WO
Inventors: Timo Luukas
Original assignee: L'oreal
Priority date: 2004-03-19
Filing date: 2005-02-25
Publication date: 2005-10-27

Abstract

The invention relates to a cosmetic or pharmaceutical composition comprising, in a physiologically acceptable medium, at least one type of polymer containing at least one type of novel monomer compound of formula (I) exhibiting optical properties. Said invention also relates to a cosmetic method for making up or treating keratinous materials, in particular the body or face skin, lips, nails, eyebrows, eyelashes and/or hairs, including the application of said cosmetic composition to said materials. Novel monomer compounds exhibiting optical properties, polymers containing said compounds and the use thereof in a composition in order to transfer the optical properties to said composition, in particular fluorescence are also disclosed.

Description

Composition comprising a monomeric compound with optical effect, process using said composition, monomeric compound and polymer comprising it

The present invention relates to new cosmetic or pharmaceutical compositions, in particular for topical application, and in particular new makeup compositions, comprising organic polymers having specific optical properties, in particular of fluorescence. The invention also relates to new monomeric compounds having optical properties, in particular to fluorescence, as well as the polymers capable of being prepared from these compounds.

Cosmetic compositions, and in particular makeup compositions such as loose or compact powders, foundations, blushes or eye shadows, lipsticks or nail varnishes, generally consist of a suitable veticle. property and of one or more coloring agents intended to impart a certain color to said compositions before and / or after their application to the skin, mucous membranes, semi-mucous membranes and / or integuments such as nails, eyelashes or c eveu-x. To create colors, a fairly limited range of coloring agents is used today, including lacquers, mineral pigments, organic pigments and pearlescent pigments.

The pigments and lacquers used in the make-up field are of very diverse origin and chemical nature. Their physico-chemical properties, in particular grain size, specific surface, density, etc., are therefore very different. These differences translate into variations in behavior: their ease of implementation, of dispersion in the environment; their stability to light and temperature; their mechanical properties. Mineral pigments, in particular mineral oxides are on the contrary very stable to light and to pH but give rather dull and pale colors. It is therefore necessary to introduce a large amount of it in cosmetic formulations to obtain a sufficiently saturated trait. This high percentage of mineral particles can nevertheless affect the gloss of the composition. Pearlescent pigments mean that varied but not very intense colors can be obtained, which lead to iridescent effects, but most often quite weak. In the field of temporary or fleeting hair coloring, which gives rise to a slight modification of the natural color of the hair which takes from one shampoo to another and which serves to embellish or correct a shade already obtained, we have already proposed coloring with usual pigments to bring a temporary reflection to the hair, but the nuances obtained by this coloring remain quite dull, too uniform and not very playful.

In the field of make-up, only organic lacquers have so far made it possible to obtain bright and intense colors. However, most organic lacquers exhibit very poor light fastness, which results in a very clear attenuation of their color over time. They can also be unstable at temperature and or at pH. In addition, some lacquers generate- rent too much disgorgement, that is to say that they have the disadvantage of staining the support on which they are applied. Thus, this can have the result of staining the eye lenses in the case of eyeliners or mascaras, or of leaving a discoloration on the skin or the nails after makeup removal in the case of lipsticks or nail varnishes . Finally, the instability of lacquers is further aggravated when they are combined with photoreactive pigments such as titanium dioxide. However, these pigments are very widely used in makeup, in particular for protection against UV radiation. Consequently, the use of organic lacquers in cosmetics is fairly limited, which results in a limitation of the achievable shades.

Thus there remains the need to have organic polymers with optical properties, capable of being used in cosmetics, making it possible to obtain adequate optical effects of the compositions comprising them and / or of the makeup obtained using these compositions, said polymers moreover having good thermal and photochemical stability, while exhibiting low bleeding. After much research, the Applicant has demonstrated that the use of a very precise family of polymers, in fact comprising at least one very specific monomer, makes it possible to obtain such a result unexpectedly.

Thus, the subject of the invention is a cosmetic or pharmaceutical composition comprising, in a physiologically acceptable medium, at least one polymer comprising at least one monomeric compound as defined below.

Another subject of the invention is a cosmetic method for making up or caring for keratin materials, in particular the skin of the body or of the face, lips, nails, eyelashes, eyebrows and / or hair, comprising application to said materials of such a cosmetic composition.

The polymers according to the invention can be in solid or liquid form, and confer remarkable optical effects on the compositions which comprise them as well as on the deposited makeup; in particular, they can provide lightening or color effects. These optical effects can advantageously be modulated as a function of the chemical nature and / or of the position of the various substituents present on the monomer with optical effect used to form the polymer.

Among the other advantages which the polymers according to the invention can provide, their good temperature, pH and light stability can be noted.

It was also found that the polymers according to the invention exhibited good solubility in fatty substances, solubility which could vary and be adjusted, depending on the nature of the monomers. This good lipid solubility can also facilitate their subsequent implementation, in particular in cosmetic compositions which generally comprise an oily phase.

In addition, the good cosmetic properties of the compositions according to the invention are maintained, when they comprise the polymers according to the invention.

In addition, although similar in chemical structure, the polymers according to the invention can exhibit, depending on the nature of the substituents, a wide variety of optical effects, which can range from red to red / purple. This makes it possible to have a range of compounds, belonging to the same chemical family, and therefore formulated in a similar manner, which offer diversities of remarkable optical properties; this notably facilitates the work of the formulators by allowing them to keep an architecture common to all of their compositions, whatever the polymers with optical property employed.

Furthermore, the polymers used according to the invention have good fluorescence properties. It will be recalled that, in general, the fluorescent compounds absorb in the ultraviolet and the visible, and re-emit energy by fluorescence for a wavelength between 380 nm and 830 nm.

In addition, the polymers according to the invention have the advantage of being easily removed.

The composition according to the invention therefore comprises, in a physiologically acceptable medium, in particular a cosmetically or pharmaceutically acceptable medium, at least one polymer capable of being obtained by particularly radical polymerization of at least one monomer or monomeric compound of formula ( I):

in which :

- R1 is chosen from (i) a hydrogen atom, (ii) a halogen, (iii) a linear, branched and / or cyclic, saturated and / or unsaturated carbon radical, comprising 1 to 12 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ and / or optionally interrupted by one or more heteroatoms chosen from O, N, P, Si and S; (iv) a group NRR 'with R and R' being, independently of one another, a hydrogen atom or a hydro-carbon radical, linear, cyclic or branched, saturated with C1-6, in particular methyl, ethyl , propyl, isopropyl, n-butyl, iso-butyl, tert-butyl, pentyl or hexyl;

- R2 and R3, present on the same cycle or each on a different cycle, represent, independently of one another, a hydrogen, a halogen, or a group of formula -XGP (II), provided that '' at least one of the radicals R2 and / or R3 represents a group of formula (II), in which:

- X is chosen from the groups -O-, -S-, -SO-, -S0 ₂ -, -NH- or -NR- with R representing a linear, branched and / or cyclic, saturated and / or insa carbon radical - turé, comprising 1 to 30 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ , and the halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S;

- G is a divalent linear, branched and / or cyclic, saturated and / or unsaturated carbon radical comprising 1 to 32 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ , and the atoms d halogen; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S;

- P is a polymerizable group chosen from one of the following formulas

("la) (Hlb) (lllc)

in which :

- R 'represents H or a hydrocarbon radical, linear or branched, saturated in C1-6,

- X 'represents O, NH or NR "with R" representing a radical chosen from the radicals C1-6 alkyl, C6-10 aryls, (C6-10) aryl (C1-6) alkyl or (C1) alkyl -

6) aryls (C6-10), the alkyl and / or aryl groups being able to be furthermore constituted by one or more groups chosen from OH, halogen, C1 - 6 alkoxy and C6-10 aryloxy; preferably X 'represents O;

- m is 0 or 1;

- n is 0 or 1;

- p is equal to 0, 1 or 2.

In the present invention, the term "cyclic radical" means a monocyclic or polycyclic radical, which therefore presents itself in the form of one or more cycles, saturated and / or unsaturated, optionally substituted (for example cyclohexyl, cyclodecyl , benzyl or fluorenyl), but also a radical which comprises one or more of the said rings (for example 4-hydroxybenzyl).

In the present invention, the term “saturated and / or unsaturated radical” is understood to mean totally saturated radicals, totally unsaturated radicals, including aromatic radicals, as well as radicals comprising one or more double and / or triple bonds, the rest of the bonds being single bonds.

Preferably, R1 is hydrogen.

Preferably, R2 is a hydrogen atom, and therefore R3 is a group of formula (II).

In said group of formula (II), X is preferably chosen from -O- and - NR- with R preferably representing a linear, branched and / or cyclic, saturated or unsaturated hydrocarbon radical, optionally comprising a hydrocarbon ring itself saturated or unsaturated, comprising 2 to 18, in particular 3 to 12 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ , and the halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S; In particular, R can be an ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclohexyl, octyl, cyclooctyl, decyl, cyclodecyl, dodecyl, cyclododecyl, phenyl or benzyl radical.

The divalent radical G is preferably a linear, branched and / or cyclic, saturated or unsaturated divalent hydrocarbon radical, optionally comprising a hydrocarbon ring itself saturated or unsaturated, comprising in total 2 to 18, in particular 3 to 10 atoms of carbon, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ , and halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si. Preferably G is chosen from saturated linear or branched divalent hydrocarbon radicals optionally comprising a saturated hydrocarbon ring, comprising in total 2 to 18, in particular 3 to 10 carbon atoms. Thus G can be chosen from the ethylene, n-propylene, isopropylene (or methyl-1 ethylene and methyl-2 ethylene), n-butylene, isobutylene, pentylene, especially n-pentylene, hexylene, especially n-hexylene, cyclohexylene, heptylene, radicals. octylene, cyclooctylene, decylene, cyclodecylene, cyclohexyldimethylene in particular of formula -CH2-C ₆ Hιo-CH ₂ -, dodecylene, cyclododecylene.

In the formula (lllb), if n = 0 then preferably, m = 0.

The polymerizable group P is preferably chosen from one of the following formulas:

in which R 'represents H or methyl.

Among the monomeric compounds which are particularly preferred according to the invention, mention may be made of the compounds corresponding to one of the following formulas, in which R is H or methyl:

Another subject of the present invention is a monomeric compound of formula (I) below:

in which

- R1 is chosen from (i) a hydrogen atom, (ii) a halogen, (iii) a linear, branched and / or cyclic, saturated and / or unsaturated carbon radical comprising 1 to 12 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ and / or optionally interrupted by one or more heteroatoms chosen from O, N, P, Si and S; (iv) a group NRR 'with R and R' being, independently of one another, a hydrogen atom or a hydrocarbon radical, linear, cyclic or branched, saturated with C1-6, in particular methyl, ethyl, propyl , isopropyl, n-butyl, iso-butyl, tert-butyl, pentyl or hexyl;

- R2 and R3, present on the same cycle or each on a different cycle, represent, independently of one another, a hydrogen, a halogen, or a group of formula -XGP (II), provided that at least one of the radicals R2 and / or R3 represents a group of formula (II), in which:

- X is chosen from the groups -O-, -S-, -SO-, -S0 ₂ - or -NR- with R representing a linear, branched and / or cyclic, saturated and / or unsaturated carbon radical, comprising 1 to 30 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ , and the halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S;

P is a polymerizable group chosen from one of the following formulas:

("la) (lllb) (lllc) in which: - R 'represents H or a hydrocarbon radical, linear or branched, saturated in C1-6,

- X 'represents O, NH or NR "with R" representing a radical chosen from C1-6 alkyl, C6-10 aryl, (C6-10) aryl (C1-6) or C1-6 alkyl radicals ) aryls (C6-10), the alkyl and / or aryl groups possibly also being substituted by one or more groups chosen from OH, halogen, C1-6 alkoxy and C6-10 aryloxy; preferably X 'represents O;

- m is 0 or 1;

- n is 0 or 1;

- p is equal to 0, 1 or 2.

Another subject of the invention is a polymer comprising at least one such monomeric compound.

Another object of the invention is the use of at least one such monomeric compound or of such a polymer comprising it, in a composition, to confer on said composition optical effects, in particular of fluorescence.

The new monomers, and the polymers comprising them, have good optical properties and are capable of being prepared more easily than those of the prior art. Particularly with a view to industrial exploitation, compounds, monomers and polymers are sought, the reactivity of which is high, which allows a short reaction time (polymerization). We are also looking for monomers and polymers with good optical properties, with a wide color palette, and capable of being used in cosmetics.

It has been found that with the compounds according to the present invention, the polymerization is easier, in particular by the presence of a spacer group (G).

In addition, the polymers and monomeric compounds according to the invention find a very particular use for conferring on a composition optical effects, in particular of fluorescence.

Some of these compounds can in particular be prepared according to the state of the art, for example according to the teaching of document EP728745, in particular the compounds for which X is N.

In a schematic way, the general process of synthesis, for the compounds for which X is O, can be represented as follows:

It is thus possible to react the appropriate naphthalic anhydride with an adequate primary diamine.

Preferably, the naphthalic anhydride is present in slight excess relative to the diamine, in particular at a rate of 1.5 equivalents, preferably 1.1 equivalents, for 1 equivalent of diamine. The reaction can be carried out in a solvent chosen by the solvents in which the anhydride is soluble, and in particular toluene, xylene, acetic acid or NMP; the reaction is preferably carried out at reflux of the solvent, for example at a temperature of 50-250 ° C, preferably 80-160 ° C. Then the isoquinolinone formed can be reacted with a diol, an amino alcohol or a thio alcohol.

For example, when R'2 is a halogen (preferably chlorine or bromine), it is possible to carry out an aromatic nucleophilic substitution, for example by using a diol such as 1,3-propane-diol or "1, 5-propane-diol, optionally in the form of an alkali metal alcoholate (sodium for example). The reaction can be carried out in the absence of solvent, or in the presence of an aprotic dipolar solvent such as dichloromethane, THF ( tetrahydrofuran), especially at a temperature of 20-150 ° C.

The corresponding alcoholic derivative is then obtained which can then be reacted with a (meth) acryloyl halide, in particular a chloride, so as to form the corresponding (meth) acrylate.

This reaction can be carried out in the presence of a base such as triethanolamine, in a solvent such as tetrahydrofuran or dichloromethane, in particular at a temperature of -30 ° C to 100 ° C, preferably 0 to 80 ° C .

The monomeric compounds for which X is S can be prepared in a similar manner. It is in particular possible to react the isoquinolinone formed in the first step above, with an alkali metal alcoholate of thioalcohol so as to form the alcoholic derivative according to the diagram below:

This derivative can then be oxidized under mild conditions so as to lead to the corresponding sulfoxide. By modifying the oxidation conditions, it is also possible to prepare the corresponding sulfone. These sulfides, sulfoxides and sulfones can then be transformed to obtain the desired methacrylates or acrylates.

These monomeric compounds can be used as the first monomer to prepare copolymers comprising them.

In particular, the monomeric compounds with optical effect according to the invention can be used to prepare homopolymers or copolymers comprising only monomeric compounds with optical effect of formula (I), alone or as a mixture, or else of formula (I) as a mixture with others, in particular as a mixture with those of formula A as defined below, these various compounds then being able, for example, to be present each in an amount of 0.5 to 99.5% by weight, especially 5 to 95% by weight, or even 10 to 90 *% by weight, even better each at a rate of 30 to 70% by weight, relative to the total weight of the polymer. This can in particular make it possible to prepare polymers having a wide palette of optical effect (color in particular, fluorescent or other).

Among the monomeric compounds with an optical effect capable of being copolymerized with the monomeric compounds of formula (I), and optionally with one or more of the additional comonomers as defined below, mention may be made of the compounds of formula (A) :

in which :

- Ra1 represents a linear, branched and / or cyclic, saturated and / or unsaturated carbon radical comprising 1 to 32 carbon atoms; optionally substituted by one or more groups chosen from = 0, OH, MH ₂ , and halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S;

- Ra2 and Ra3, present on the same cycle or each on a different cycle, represent, independently of one another, a hydrogen, a halogen, or a group of formula -Xa-Ga-Pa (II) , provided that at least one of the radicals Ra2 and / or Ra3 represents a group of formula (II), in which:

- Xa is chosen from the groups -O-, -S-, -SO-, -SO ₂ -, -NH- or -NR4- with R4 representing a linear, branched and / or cyclic, saturated and / or unsaturated carbon radical , comprising 1 to 30 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, MH ₂ , and the halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S;

- Ga is a divalent linear, branched and / or cyclic, saturated and / or unsaturated carbon radical comprising 1 to 32 carbon atoms, optionally substituted by a or several groups chosen from = 0, OH, NH, and halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S;

- Pa is a polymerizable group chosen from one of the following formulas:

( ^llla ) (lllb) (Nie) in which:

- X 'represents O, NH or NR "with R" representing a radical chosen from C1-6 alkyl, C6-10 aryl, (C6-10) aryl (C1-6) or C1-6 alkyl radicals ) aryls (C6-10), the alkyl and / or aryl groups possibly also being substituted by one or more groups chosen from OH, halogen, C1-6 alkoxy and C6-10 aryloxy; and

- m is 0 or 1; n is 0 or 1; p is 0, 1 or 2.

It is also possible to prepare random, alternating or grafted copolymers comprising said monomeric compounds with an optical effect according to the invention and additional comonomers as defined below.

It is also possible to prepare block copolymers, for example diblock or triblock, comprising said monomeric compounds with optical effect according to the invention and additional comonomers as defined below. The monomeric compounds according to the invention can form all or part of a block, or sequence, or even of several blocks or sequences. It is thus possible to prepare block copolymers of the type AB, ABA, BAB, ABC where A is a block comprising the monomeric compound or compounds according to the invention, optionally in admixture with additional comonomers, B and C being distinct blocks, comprising additional comonomers, alone or as a mixture, and identical or different from the comonomers present in sequence A.

The copolymers comprising the monomeric compounds according to the invention can also be of the gradient type.

In these copolymers, the monomeric compounds with an optical effect can be present in an amount of 0.01 to 70% by weight relative to the weight of the final polymer, in particular in an amount of 0.1% to 50% by weight, in particular of 0.5 to 30% by weight, or even 1 to 20% by weight, even better from 2 to 10% by weight, the additional comonomers, alone or in mixture, representing the complement to 100% by weight.

The copolymers according to the invention may comprise, in addition to the monomeric compound or compounds with an optical effect, at least one additional comonomer which is hydrophilic, or a mixture of such comonomers.

These hydrophilic comonomers can be present in a proportion of 1 to 9> 9.99% by weight, especially 2-70% by weight, even better 5-50% by weight, or even 10-30% by weight, relative to the total weight of the copolymer.

In the present description, the term “hydrophilic monomer” will denote either the monomers whose homopolymers are soluble or dispersible in water, or whose ionic form is. A homopolymer is said to be water-soluble if it forms a clear solution when it is in solution at 5% by weight in water, at 25 ° C.

A homopolymer is said to be water-dispersible if, at 5% by weight in water, at 25 ° C, it forms a stable suspension of fine particles, generally spherical. The average size of the particles constituting said dispersion is less than 1 μm and, more generally, varies between 5 and 400 nm, preferably from 10 to 250 nm. These particle sizes are measured by light scattering. A monomer will be called 'hydrophobic' if it is not hydrophilic.

Preferably, the hydrophilic additional comonomer (s) has a Tg greater than or equal to 20 ° C., in particular greater than or equal to 50 ° C., but may optionally have a Tg less than or equal to 20 ° C.

The copolymers according to the invention can comprise at least one additional hydrophobic comonomer, or a mixture of such comonomers. These additional hydrophobic comonomers can be present in an amount of 1 to 99.99% by weight, especially 30-98% by weight, even better 50-95 ^% and by weight, or even 70-90% by weight, relative to the weight. total of the copolymer. Preferably, the hydrophobic comonomer has a Tg greater than or equal to 20 ° C., in particular greater than or equal to 30 ° C., but can optionally have a Tg less than or equal to 20 ° C.

In the present invention, the Tg (or glass transition temperature) is measured according to standard ASTM D3418-97, by differential enthalpy analysis (DSC "Differential Scanning Calorimetry") on a calorimeter, over a temperature range between -100 ° C. and + 150 ° C at a heating rate of 10 ° C / min in 150 μl aluminum crucibles. In general, as additional comonomer capable of being copolymerized with at least one monomeric compound of formula (I), the following monomers may be mentioned, alone or as a mixture:

- (i) ethylenic hydrocarbons having 2 to 10 carbons, such as ethylene, isoprene, or butadiene;

(ii) the (meth) acrylates of formula: CH,

H ₂ C = C COOR ₃

CH ₂ = CHCOOR ₃ or in which R ₃ represents:

- a linear or branched alkyl group, from 1 to 18 carbon atoms, in which there are optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group possibly also being optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (RjRs), where t and R5 are identical or different represent a C1-C6 alkyl group or a phenyl group; in particular R3 can be a methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, isooctyl, isodecyl, dodecyl, cyohexyl, t-butylcyclohexyl or stearyl group; ethyl-2-perfluorohexyl; or hydroxyalkyl group having _{1 to} ₄ such as 2-hydroxyethyl, 2-hydroxybutyl and 2-hydroxypropyl; or an alkoxy group (Cι- ₄ ) alkyl (Cι-) such as methoxyethyl, ethoxyethyl and methoxypropyl,

a C ₃ to C ₁₂ cycloalkyl group, such as the isobornyl group,

a C 3 to C ₂₀ aryl group such as the phenyl group, a C ₄ to C ₃₀ aralkyl group (C 1 to C ₈ alkyl group) such as 2-phenylethyl, t-butylbenzyl or benzyl,

a heterocyclic group of 4 to 12 members containing one or more heteroatoms chosen from O, N and S, the ring being aromatic or not,

a heterocycloalkyl group (alkyl of 1 to 4 C), such as furfurylmethyl & or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups which may be optionally substituted by one or more substituents chosen from hydroxyl groups, atoms of 'halogen, and C1-4 alkyl groups, linear or branched in which there is (are) optionally intercalated (s) one or more heteroatoms chosen from O, N, S and P, said alkyl groups being able, in addition, to be optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (F ^ Rs), where R ₄ and R _{5, which are} identical or different, represent a group C1 to C6 alkyl, or a phenyl group, - R ₃ can also be a group - (C ₂ H ₄ 0) _m -R ", with m = 5 to 150 and R" = H or C1 to C ₃ o alkyl, for example -POE-methyl or -POE -béhényle;

- (Ni) the (meth) acrylamides of formula:

R6 /

H ₉ C = C CO-N ² \ R7 in which R ₈ denotes H or methyl; and R ₇ and R _{6, which are} identical or different, represent:

- a hydrogen atom; or - a linear or branched alkyl group of 1 to 18 carbon atoms, in which there are optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group possibly also being optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (R4R ₅ ) - where R ₄ and R _5, identical or different, represents a C1-C6 alkyl group or a phenyl group; in particular R3 may be a methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, isooctyl, isodecyl, dodecyl, cyo-clohexyl, t-butylcyclohexyl or stearyl group; ethyl-2-perfluorohexyl; or hydroxyalkyl group having _{1 to} ₄ such as 2-hydroxyethyl, 2-hydroxybutyl and 2-hydroxypropyl; or an alkoxy group (Cι- ₄ ) alkyl (C1-4) such as methoxyethyl, ethoxyethyl and methoxypropyl,

a C ₃ to C ₁₂ cycloalkyl group, such as the isobornyl group,

a C ₃ to C ₂₀ aryl group such as the phenyl group,

a C ₄ to C ₃₀ aralkyl group (C 1 to C ₈ alkyl group) such as 2-phenylethyl, t-butylbenzyl or benzyl,

a heterocycloalkyl group (alkyl of 1 to 4 C), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups which may be optionally substituted by one or more substituents chosen from hydroxyl groups, atoms of 'halogen, and C1-C4 alkyl groups, linear or branched in which is (are) optionally intercalated ^) one or more heteroatoms chosen from O, N, S and P, said alkyl groups being able, in addition, be optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (CI, Br, I and F), and Si groups (R ₄ R ₅ ), where R ₄ and R _{5 are} identical or different represent alkyl to C _6, or a phenyl group. Examples of (meth) acrylamide monomers are (meth) acrylamide, N-ethyl (meth) acrylamide, N-butylacrylamide, Nt-butylacrylamide, N-isopropylacrylamide, N, N-dimethyl (meth) acrylamide, the

N, N-dibutylacrylamide, N-octylacrylamide, N-dodecylacrylamide, Pundecylacrylamide, and N (2-hydroxypropylmethacrylamide).

- (iv) the vinyl compounds of formulas: CH ₂ = CH-R ₉ , CH ₂ = CH-CH ₂ -R ₉ or CH2 = C (CH ₃ ) -CH ₂ -R ₉ in which Rg is a hydroxyl group, halogen (Cl or F), NH _2, oR 1 wherein R ₀ _ι-0 represents a phenyl group or an alkyl group at C ₁₂ (the monomer is a vinyl or allylic ether); acetamide (NHCOCH ₃ ); an OCORn group where Ru represents an alkyl group of 2 to 12 carbons, linear or branched (the monomer is a vinyl or allyl ester); or a group chosen from:

- a linear or branched alkyl group, from 1 to 18 carbon atoms, in which there are optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group possibly also being optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (R4R5), where R4 and R5 are identical or different represent a C1-C6 alkyl group or a phenyl group; a C ₃ to C ₁₂ cycloalkyl group such as isobornyl, cyclohexane,

a C ₃ to C ₂₀ aryl group such as phenyl,

- a C ₄ to C ₃₀ aralkyl group (C 1 to C ₈ alkyl group) such as 2-phenylethyl; benzyl,

a 4 to 12-membered heterocyclic group containing one or more heteroatoms chosen from O, N and S, the ring being aromatic or not,

a heterocycloalkyl group (alkyl of 1 to 4 C), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups which may be optionally substituted by one or more substituents chosen from hydroxyl groups, atoms of 'halogen, and alkyl groups of 1 to 4 C linear or branched in which there are (are) optionally intercalated (s) one or more heteroatoms chosen from O, N, S and P, said alkyl groups being able, in addition, to be optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F) and Si (Rs) groups where Ri and R _{2, which are} identical or different, represent a C 1 to C ₆ alkyl group , or a phenyl group.

Examples of vinyl monomers are vinylcyclohexane, and styrene. Examples of vinyl esters are vinyl acetate, vinyl propionate, vinyl butyrate, vinyl ethylhexanoate, vinyl neononanoate and vinyl neododecanoate.

Among the vinyl ethers, mention may be made of vinyl methyl ether, vinyl ethyl ether and vinyl isobutyl ether. - (v) (meth) acrylic, (meth) acrylamide or vinyl monomers containing a fluorinated or perfluorinated group, such as ethyl-perfluorooctyl or ethyl-2-perfluorohexyl (meth) acrylate;

- (vi) (meth) acrylic, (meth) acrylamides or silicone vinyl monomers, such as methacryloxypropyltris (trimethylsiloxy) silane or acryloxypropylpoly-dimethylsiloxane.

- (vii) the ethylenically unsaturated monomers comprising at least one carboxylic, phosphoric or sulfonic acid or anhydride function, such as for example acrylic acid, methacrylic acid, crotonic acid, maleic anhydride, itaconic acid, fumaric acid, maleic acid, acrylamide-dopropanesulfonic acid, vinyl benzoic acid, vinyl phosphoric acid and the salts thereof,

- (viii) ethylenically unsaturated monomers comprising at least one tertiary amine function such as 2-vinylpyridine, 4-vinylpyridine, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, dimethylaminopropyl methacrylamide and the salts thereof.

The salts can be formed by neutralization of the anionic groups using a mineral base, such as LiOH, NaOH, KOH, Ca (OH) ₂ , NH ₄ OH or Zn (OH) ₂ ; or by an organic base such as a primary, secondary or tertiary alkylamine, in particular triethylamine or butylamine. This primary, secondary or tertiary alkylamine can comprise one or more nitrogen and / or oxygen atoms and can therefore comprise, for example, one or more alcohol functions; mention may be made of amino-2-methyl-2-propanol, triethanolamine and dimethylamino-2-propanol. Mention may also be made of lysine or 3- (dimethylamino) -propylamine.

Mention may also be made of the salts of mineral acids, such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, boric acid. Mention may also be made of the salts of organic acids, which may contain one or more carboxylic, sulphonic or phosphonic acid groups. They can be linear, branched or cyclic aliphatic acids or even aromatic acids. These acids may also contain one or more heteroatoms chosen from O and N, for example in the form of hydroxyl groups. Mention may in particular be made of propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid. It is obviously possible to use several of the additional comonomers mentioned above.

The additional comonomer (s) may be present in an amount from 30% to 99.99% by weight relative to the weight of the final polymer, in particular in an amount from 50% to 99.9% by weight, in particular from 70% to 99.5% by weight, even from 80 to 99% by weight, even better from 90 to 98% by weight.

The additional comonomers are chosen more particularly from, alone or as a mixture, C1-C18 alkyl (meth) acrylates or C3-C12 cycloalkyl, and in particular from methyl acrylate, methyl methacrylate, isobornyl acrylate, isobornyl methacrylate, isobutyl acrylate, isobutyl methacrylate, ethyl-2-hexyl acrylate, ethyl-2-hexyl methacrylate, dodecyl acrylate , dodecyl methacrylate, stearyl acrylate, stearyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate.

Mention may also be made of acrylic acid, methacrylic acid, methacryloxypropyltris (trimethylsiloxy) silane, acryloxypropyltris (trimethylsiloxy) silane, acryloxypropylpolydimethylsiloxane and methacryloxypropylpolydimethylsiloxane.

Said polymers can be prepared according to methods known to those skilled in the art, in particular by radical polymerization; controlled radical polymerization, for example with xanthans, dithiocarbamates or dithioesters; by polymerization using nitroxide type precursors; by radical atom transfer polymerization (ATRP); by group transfer polymerization.

Conventionally, the polymerization can be carried out in the presence of a polymerization initiator, which can be a radical initiator, and in particular which can be chosen from organic peroxide compounds such as dilauroyl peroxide, dibenzoyl peroxide, ter -butyl peroxy-2-ethylhexanoate; or alternatively among diazotized compounds such as azobisisobutyronitrile or Pazobisdimethylvaleronitrile. The reaction can also be initiated using photoinitiators or by UV-type radiation, by neutrons or by plasma.

The monomeric compounds with an optical effect, as well as optionally the homo- or co-polymers comprising them, preferably have an absorption wavelength between 300 and 700 nm, in particular between 320 and 650 nm, or even between 350 and 600 nm .

They preferably have an emission wavelength between 380 and 850 nm, in particular between 400 and 750 nm, or even between 450 and 700 nm. The weight-average molecular mass (Mw) of the copolymers according to the invention is preferably between 5000 and 600,000 g / mol, in particular between 10,000 and 300,000 g / mol, and even better between 20,000 and 150,000 g / mol. The weight average molecular weights (Mw) and number (Mn) are determined by liquid gel permeation chromatography (GPC), eluent THF, calibration curve established with linear polystyrene standards, refractometric detector.

The polymers according to the invention, whether they are homopolymers or copolymers, can be present, alone or as a mixture, in the compositions according to the invention in an amount of 0.01 to 60% by weight, preferably 0.1 to 50% by weight, in particular 1 to 25% by weight, or even 3 to 15% by weight, and even better 5 to 12% by weight, relative to the total weight of the composition.

They may be present in the composition in dissolved form, for example in water, in an oil or in an organic solvent, or else in the form of an aqueous or organic dispersion.

Advantageously, the polymers according to the invention are soluble or dispersible in at least one of the phases of the composition which comprises them.

The cosmetic or pharmaceutical compositions according to the invention comprise, in addition to said polymers, a physiologically acceptable medium, in particular cosmetically, dermatologically or pharmaceutically acceptable, that is to say a medium compatible with keratin materials such as the skin of the face or body, hair, eyelashes, eyebrows and nails.

The composition can thus comprise, a hydrophilic medium comprising water or a mixture of water and organic solvent (s) hydrophilic (s) such as alcohols and in particular linear or branched lower monoalcohols having from 2 to 5 carbon atoms such as ethanol, isopropanol or n-propanol, and polyols such as glycerin, diglycerin, propylene glycol, sorbitol, pentylene glycol, and polyethylene glycols, or even C ethers ₂ and hydrophilic C ₂ -C ₄ aldehydes. The water or the mixture of water and hydrophilic organic solvents may be present in the composition according to the invention in a content ranging from 0.1% to 99% by weight, relative to the total weight of the composition, and preferably 10% to 80% by weight. The composition can also be anhydrous.

The composition can also comprise a fatty phase which can comprise fatty substances liquid at ambient temperature (25 ° C. in general) and / or fatty substances solid at ambient temperature such as waxes, fatty substances gums, gums and their mixtures. These fatty substances can be of animal, vegetable, mineral or synthetic origin. This fatty phase can, in addition, contain lipophilic organic solvents.

As fatty substances liquid at room temperature, often called oils, which can be used in the invention, mention may be made of: hydrocarbon oils of animal origin such as perhydrosqualene; vegetable hydrocarbon-based oils such as liquid triglycerides of fatty acids with 4 to 10 carbon atoms such as triglycerides of heptanoic or octanoic acids, or even sunflower, corn, soybean, grape seed, sesame oils, apricot, macadamia, castor, avocado, caprylic / capric acid triglycerides, jojoba oil, shea butter; linear or branched hydrocarbons, of mineral or synthetic origin such as paraffin oils and their derivatives, petrolatum, polydecenes, hydrogenated polyisobutene such as parlameam; synthetic esters and ethers, in particular of fatty acids such as, for example, Purcellin oil, isopropyl myristate, ethyl-2-hexyl palmitate, octyl-2-dodecyl stearate, erucate octyl-2-dodecyl, isostearyl isostearate; hydroxyl esters such as isostearyl lactate, octylhydroxystearate, octyldodecyl hydroxystearate, diisostearylmalate, triisocetyl citrate, heptanoates, octanoates, decanoates of fatty alcohols; polyol esters such as propylene glycol dioctanoate, neopentylglycol diheptanoate, diethylene glycol diisononanoate; and pentaerythritol esters; fatty alcohols having from 12 to 26 carbon atoms such as octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleic alcohol; partially hydrocarbon and or silicone fluorinated oils; silicone oils such as polymethylsiloxanes (PDMS) volatile or not, linear or cyclic, liquid or pasty at room temperature such as cyclomethicones, dimethicones, optionally comprising a phenyl group, such as phenyl trimethicones, phenyltrimethylsiloxydiphenyl siloxanes, diphenylmethyldimethyl-trisilanes diphenyl dimethicones, phenyl dimethicones, polymethylphenyl siloxanes; their mixtures.

These oils can be present in a content ranging from 0.01 to 90%, and better still from 0.1 to 85% by weight, relative to the total weight of the composition.

The composition according to the invention can also comprise one or more organic solvents, physiologically acceptable.

These solvents can generally be present in a content ranging from 0.1 to

90%, preferably from 0.5 to 85%, more preferably from 10 to 80% by weight, relative to the total weight of the composition, and better still from 30 to 50%.

Mention may in particular be made, in addition to the hydrophilic organic solvents mentioned above, ketones which are liquid at room temperature such as methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, isophorone, cyclohexanone, acetone; propylene glycol ethers liquid at room temperature such as mono- propylene glycol methyl ether, propylene glycol monomethyl ether acetate, dipropylene glycol mono n-butyl ether; short chain esters (having 3 to 8 carbon atoms in total) such as ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate, acetate d isopentyl; ethers liquid at 25 ° C such as diethyl ether, dimethyl ether or dichlorodiethyl ether; alkanes liquid at 25 ° C such as decane, heptane, dodecane, isododecane, cyclohexane; aromatic cyclic compounds liquid at 25 ° C such as toluene and xylene; aldehydes liquid at 25 ° C such as benzaldehyde, acetaldehyde and their mixtures.

By wax within the meaning of the present invention is meant a lipophilic compound, solid at room temperature (25 ° C.), with reversible solid / liquid state change, having a melting point greater than or equal to 25 ° C. up to 'at 120 ° C. By bringing the wax to the liquid state (melting), it is possible to make it miscible with the oils possibly present and to form a homogeneous mixture microscopically, but by bringing the temperature of the mixture to room temperature, one obtains recrystallization of the wax from the oils in the mixture. The melting point of the wax can be measured using a differential scanning calorimeter (D.S.C.), for example the calorimeter sold under the name DSC 30 by the company METLER.

The waxes can be hydrocarbon, fluorinated and / or silicone and be of vegetable, mineral, animal and / or synthetic origin. In particular, the waxes have a melting point greater than 30 ° C and better still greater than 45 ° C. As wax which can be used in the composition of the invention, mention may be made of beeswax, Carnauba or Candellila wax, paraffin, microcrystalline waxes, ceresin or ozokerite; synthetic waxes such as polyethylene or Fischer Tropsch waxes, silicone waxes such as alkyl or alkoxy-dimethicone having from 16 to 45 carbon atoms. The gums are generally high molecular weight polydimethylsiloxanes (PDMS) or cellulose gums or polysaccharides and the pasty bodies are generally hydrocarbon compounds such as lanolines and their derivatives or PDMS.

The nature and quantity of the solid bodies depend on the mechanical properties and the desired textures. As an indication, the composition may contain from 0.1 to 50% by weight of waxes, relative to the total weight of the composition and better still from 1 to 30% by weight.

The composition according to the invention can also comprise, in a particular phase, pigments and / or nacres and / or fillers usually used in cosmetic compositions. The composition can also comprise other coloring materials chosen from water-soluble dyes and / or liposoluble dyes well known to those skilled in the art.

The term “pigments” should be understood to mean particles of any shape, white or colored, mineral or organic, insoluble in the physiological medium, intended to color the composition.

By fillers, it is necessary to understand colorless or white, mineral or synthetic particles, lamellar or non-lamellar, intended to give body or rigidity to the composition, and / or softness, mattness and uniformity. makeup.

By nacres, it is necessary to understand particles of any iridescent shape, in particular produced by certain molluscs in their shell or else synthesized. The pigments can be present in the composition in an amount of 0.01 to 25% by weight of the final composition, and preferably in an amount of 3 to 10% by weight. They can be white or colored, mineral or organic. Mention may be made of titanium, zirconium or cerium oxides, as well as zinc, iron or chromium oxides, ferric blue, chromium hydrate, carbon black, ultramarines (aluminosilicate polysulphides) , manganese pyrophosphate and certain metallic powders such as those of silver or aluminum. Mention may also be made of the D&C pigments and the lacquers commonly used to give the lips and the skin a makeup effect, which are calcium, barium, aluminum, strontium or zirconium salts.

The nacres can be present in the composition in an amount of 0.01 to 20% by weight, preferably at a rate of the order of 3 to 10% by weight. Among the possible nacres, mention may be made of natural mother-of-pearl, mica coated with titanium oxide, iron oxide, natural pigment or bismuth oxychloride as well as colored titanium mica.

Among the dyes, liposoluble or water-soluble, which may be present in the composition, alone or as a mixture, at a rate of 0.001 to 15% by weight, preferably 0.01 to 5% by weight and in particular from 0.1 to 2% by weight, relative to the total weight of the composition, there may be mentioned the disodium salt of culvert, the sodium salt of alizarin green, quinoline yellow, the trisodium salt of amaranth, the disodium salt of tartrazine, monosodium salt of rhodamine, disodium salt of fuchsin, xanthophyll, methylene blue, cochineal carmine, halo-acid, azo, anthraquinone dyes, copper or iron sulfate, Sudan brown , Sudan red and annatto, as well as beet juice and carotene.

The composition according to the invention may also further comprise one or more fillers, in particular in a content ranging from 0.01% to 50% by weight, relative to the total weight of the composition, preferably ranging from 0.02% at 30% by weight. The fillers can be mineral or organic in any form, platelet, spherical or oblong. We can mention talc, mica, silica, kaolin, polyamide (Nylon®), poly-β-alanine and polyethylene powders, powders of tetrafluoroethylene polymers (Teflon®), lauroyl-lysine, starch, boron nitride, hollow polymeric microspheres such as those of polyvinylidene chloride / acrylonitrile such as PExpancel® (Nobel Industry), of acrylic acid copolymers (Polytrap® of the company Dow Corning) and the microbeads of silicone resin (Tospearls® of Toshiba, for example), the particles of elastomeric polyorganosiloxanes, precipitated calcium carbonate, magnesium carbonate and hydrocarbon, hydroxyapatite, hollow silica microspheres (Silica Beads® by Maprecos), glass or ceramic microcapsules, metallic soaps derived from organic carboxylic acids having from 8 to 22 carbon atoms, preferably from 12 to 18 carbon atoms, for example zinc stearate, magnesium or lithium, zinc laurate, myristat e of magnesium.

The composition may further comprise an additional polymer such as a film-forming polymer. According to the present invention, the term "film-forming polymer" means a polymer capable of forming on its own or in the presence of an auxiliary film-forming agent, a continuous and adherent film on a support, in particular on keratin materials. Among the film-forming polymers capable of being used in the composition of the present invention, mention may be made of synthetic polymers, of radical type or of polycondensate type, polymers of natural origin and their mixtures, in particular acrylic polymers, polyurethanes , polyesters, polyamides, polyureas, cellulosic polymers such as nitrocellulose.

The composition according to the invention may also include ingredients commonly used in cosmetics, such as vitamins, thickeners, gelling agents, trace elements, softeners, sequestrants, perfumes, alkalizing or acidifying agents, preservatives, sunscreens, surfactants, antioxidants, hair loss agents, dandruff agents, propellants, ceramides, or mixtures thereof. Of course, those skilled in the art will take care to choose this or these optional additional compounds, and / or their quantity, in such a way that the advantageous properties of the composition according to the invention are not, or not substantially, affected by the planned addition.

The composition according to the invention may be in the form of a suspension, a dispersion in particular of oil in water by means of vesicles; an oily solution possibly thickened or even gelled; an oil-in-water, water-in-oil, or multiple emulsion; a gel or foam; an oily or emulsified gel; a dispersion of vesicles, in particular lipid vesicles; a biphasic or multiphase lotion; a spray; loose, compact or poured powder; an anhydrous paste. This composition may have the appearance of a lotion, a cream, an ointment, a flexible paste, an ointment, a cast or molded solid and in particular in stick or in a cup, or alternatively of compacted solid.

Those skilled in the art can choose the appropriate dosage form, as well as its method of preparation, on the basis of his general knowledge, taking into account on the one hand the nature of the constituents used, in particular their solubility in the support, and on the other hand of the application envisaged for the composition.

The cosmetic composition according to the invention may be in the form of a product for caring for and / or making up the skin of the body or of the face, lips, nails, eyelashes, eyebrows and / or hair, a sun or self-tanning product, a hair product for the care, treatment, shaping, makeup or coloring of the hair.

It can thus be in the form of a makeup composition, in particular a product for the complexion such as a foundation, a blusher or an eyeshadow; a lip product such as lipstick or lip care; a concealer; a blush, a mascara, an eyeliner; an eyebrow makeup product, a lip or eye pencil; a nail product such as nail polish or nail care; a body makeup product; a hair makeup product (mascara or hair spray). It can also be in the form of a composition for protecting or caring for the skin of the face, neck, hands or body, in particular an anti-wrinkle composition, a hydrating or treating composition; an anti-sun or artificial tanning composition.

It can also be in the form of a hair product, in particular for coloring, maintaining the hairstyle, shaping the hair, caring for, treating or cleaning the hair, such as shampoos, gels, styling lotions, brushing lotions, fixing and styling compositions such as lacquers or spray.

A subject of the invention is also a cosmetic process for making up or caring for keratin materials, in particular the skin of the body or of the face, lips, nails, eyelashes, eyebrows and / or hair, comprising application to said materials of a cosmetic composition as defined above.

The invention is illustrated in more detail in the following examples.

Wavelength measurement method (emission and absorption) The wavelengths are measured using a Varian Cary Eclipse fluorimeter.

Unless otherwise indicated, this measurement is carried out as follows: 20 mg of product are placed in a 50 ml cylinder. In order to dissolve the product, said cylinder is made up to 50 ml, using an appropriate solvent, for example dichloromethane (DCM), chloroform or dimethylsulfoxide (DMSO). The resulting solution is mixed and 250 microliters are taken from it, which is placed in a 50 ml cylinder, then made up again with the solvent to 50 ml. The whole is mixed and a sample of the solution is taken which is placed in a closed tank, quartz and 10 mm thick, which is then placed in the measurement chamber.

Example 1

Step 1: preparation of 4-chloro-naphthylisoquinolinone

In a 2-liter flask, under an inert atmosphere (nitrogen), 20.0 g (86 mmol) of 4-chloronaphthalene-1,8-anhydride are available, then 20.4 g (0.13 mol) of 1.8- are added. diaminonaphthalene and 250 ml of NMP. Mix at 500 rpm. for a few minutes, under argon, and the mixture is heated to 150 ° C. After 4 hours of reaction, the resulting reaction mixture is allowed to cool to room temperature. The precipitate is filtered, washed with ethanol and with water, then it is dried in an oven at 60 ° C, under reduced pressure. 30.2 g of brown powder are obtained (yield 98.9%)

Characterization

¹ H-NMR (CDCI ₃ , 400MHz) δ: 8.84 - 8.66 (1 H), 8.61 - 8.45 (2H), 8.43 - 8.37 (1 H),

7.79 - 7.70 (2H), 7.51 - 7.26 (4H), 7.22 - 7.18 (1H).

Step 2: preparation of naphthylisoquinolinone-4-aminoethanol

10.0 g (28.8 mmol) of 4-chloro-naphthylisoquinolinone are placed in a flask under an inert argon atmosphere; 120.0 g (1.6 mol) of N-methylaminoethan-2-ol are added, the mixture is mixed and the mixture is heated to 160 ° C. It is left to react for 8 hours and then allowed to cool to ambient temperature (25 ° C.). 150 ml of cold water are then added; the precipitate is filtered, washed with acidified water and then with water, then dried in an oven at 60 ° C, under reduced pressure. 10.3 g of brown-purple powder are obtained (yield 90.9%)

Characterization

¹ H-NMR (CDCI ₃ , 400MHz) δ: 8.75-8.35 (4H), 7.65-7.15 (7H), 3.93 - 3.91 (2H),

3.44 - 3.40 (2H), 3.02 - 2.98 (3H)

Step 3: preparation of naphthylisoquinolinone-4-N-methyl-aminoethane acrylate

4.0 g (10.2 mmol) of naphthylisoquinolinone-4-N-methyl-aminoethanol are placed in a flask under an inert argon atmosphere; 125 ml of dichloromethane (DCM) are added and the mixture is mixed until complete dissolution. With stirring, 4.6 g of triethylamine (45.9 mmol) are added. 1.1 g of acryloyl chloride (12.2 mmol) are diluted in 10 ml of DCM, and this solution is added dropwise to the reaction medium at 38 ° C. The mixture is heated to 40 ° C while maintaining stirring and allowed to react for 12 hours, then 20 ml of cold water are added. The mixture is extracted with 100 ml of an aqueous solution of sodium bicarbonate, then washed with 200 ml of water. The product is recovered which is dried in an oven at 35 ° C, under reduced pressure. 3.7 g of red-purple powder are obtained (yield 80%)

Characterization Η-NMR (CDCI ₃ , 400MHz) δ: 8.80-8.30 (4H), 7.66-7.21 (7H), 6.39-6.31 (1 H), 6.12-6.03 (1H), 5.85-5.81 (1H), 4.49 -4.46 (2H), 3.64-3.56 (2H), 3.09-3.05 (3H)

Examples 2. 3. 4 and 5

In an identical manner to Example 1, the following monomers are prepared Example 2:

example 3:

example 4:

example 5:

Example 6

Preparation of naphthylisoquinolinone-4-aminopentane-5-methacrylate

10.0 g (23.6 mmol) of naphthylisoquinolinone-4-aminopentan-5-ol prepared in Example 1 are placed in a flask under an inert argon atmosphere; 60 ml of THF are added and the mixture is mixed until complete dissolution. With stirring, 7.6 g of triethylamine (75.1 mnnol) are added. 2.6 g of methacryloyl chloride (24.9 mmol) are diluted in 15 ml of THF, and this solution is added dropwise to the reaction medium at 38 ° C. The mixture is heated to 40 ° C while maintaining stirring and allowed to react for 12 hours, then add 20 ml of cold water. The mixture is extracted with 10O ml of an aqueous solution of sodium bicarbonate, then with 200 ml of water. The product is recovered which is dried in an oven at 35 ° C, under reduced pressure. 10.1 g of red-violet powder are obtained (yield 87.2%)

Characterization

¹ H-NMR (DMSO, 400MHz) δ pprn: 8.61 - 8.18 (4H), 7.59 - 7.34 (5H), 7.07 - 7.00 (1H), 6.71 - 6.67 (1H), 6.24 (1H), 6.00 (1H), 4.38 (1H), 4.14 - 3.42 (2H), 3.33 - 3.27 (2H), 1.93 (3H), 1.74 - 1.36 (6H)

- absorption wavelength λmax absorption: 557 nm

- emission wavelength λ _ma χ emission: 644 nm (solvent: DCM) Example 7

A homopolymer is prepared from a monomer according to the invention. 2.0 g of the monomer prepared in Example 1 are dissolved in 20 ml of THF, at 60 ° C., under argon, in the presence of 0.2 g of Trigonox 141 (initiator). It is heated to 90 ° C. and then kept at this temperature and with stirring for 24 hours. The reaction medium is cooled to 50 ° C, and poured into cold acetone (-10 ° C). The filtrate precipitate is recovered and then washed with acetone and dried under reduced pressure. The corresponding homopolymer is then obtained.

Example 8

A random copolymer is prepared comprising a monomer according to the invention.

20 g of isododecane, then 39.0 g of isobornyl acrylate and 10.0 g of ethylhexyl acrylate are introduced into a reactor, under argon, equipped with a condenser and stirring. The mixture is mixed and a mixture consisting of 1.0 g of monomer from Example 1 in 20.0 g of toluene is added. 0.5 g of Trigonox 21 S (t-butyl peroxy-2-ethylhexanoate) is added, then the reaction mixture is heated to 90 ° C; stirring and heating are continued for 6 hours and then cooled to room temperature. The resulting polymer is purified by precipitation.

A statistical polymer is obtained comprising (% by weight): 78% isobornyl acrylate, 20% ethylhexyl acrylate and 2% of monomer according to the invention.

Example 9

A random copolymer is prepared comprising a monomer according to the invention.

In a reactor, under argon, equipped with a condenser and a stirrer, 20 g of isododecane are introduced, then 38.25 g of isobornyl acrylate and 10.0 g of ethylhexyl acrylate . A mixture consisting of 1.75 g of monomer from Example 2 in 20.0 g of toluene is mixed and added.

0.5 g of Trigonox 21 S (t-butyl peroxy-2-ethylhexanoate) is added, then the reaction mixture is heated to 90 ° C; stirring and heating are continued for 6 hours and then cooled to room temperature. The resulting polymer is purified by precipitation.

A statistical polymer is obtained comprising (% by weight): 76.5% of isobornyl acrylate, 20% ethylhexyl acrylate and 3.5% of monomer according to the invention.

Example 10

A random copolymer is prepared comprising a monomer according to the invention. 20 g of isododecane, then 27 g of methyl methacrylate, 17 g of methyl acrylate and 5 g of acrylic acid are introduced into a reactor, under argon, equipped with a condenser and stirring. The mixture is mixed and a mixture consisting of 1 g of monomer from Example 3 in 20.0 g of toluene is added. 0.5 g of Trigonox 21 S (t-butyl peroxy-2-ethylhexanoate) is added, then the reaction mixture is heated to 90 ° C; stirring and heating are continued for 6 hours and then cooled to room temperature. The resulting polymer is purified by precipitation.

A statistical polymer is obtained comprising (% by weight): 54% of methyl methacrylate, 34% of methyl acrylate, 10% of acrylic acid and 2% of monomer according to the invention.

Example 11

An anhydrous foundation is prepared comprising (% by weight):

- 12% polyethylene wax

- 25% volatile silicone oils

- phenyltrimethicone 20%

- Polymethylmethacrylate 12% microspheres - Polymer from Example 5 6%

- Isododecane qs 100%

Preparation:

The waxes are melted then, when everything is clear, the phenyl trimethionone is added with stirring, and the silicone oils; the microspheres, isododecane and the polymer are then added. The mixture is homogenized for 15 minutes and then the resulting composition is poured in and allowed to cool. An anhydrous foundation is obtained.

Example 12

A nail polish is prepared comprising:

- 5% by weight of polymer according to example Λ 0

- qs 100% organic solvents.

Claims

1. Cosmetic or pharmaceutical composition comprising, in a physiologically acceptable medium, at least one polymer comprising at least one monomeric compound of formula (I):

in which :

- X is chosen from the groups -O-, -S-, -SO-, -S0 ₂ -, -NH- or -NR- with R representing a linear, branched and / or cyclic, saturated and / or unsaturated carbon radical , comprising 1 to 30 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ , and the halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S;

- P is a polymerizable group chosen from one of the following formulas:

la) (lllb) (lllc)

in which :

- X 'represents O, NH or NR "with R" representing a radical chosen from C1-6 alkyl, C6-10 aryl, (C6-10) aryl (C1-6) alkyl or (C1-6) alkyl radicals ) aryls (C6-10), the alkyl and / or aryl groups possibly also being substituted by one or more groups chosen from OH, halogen, C1-6 alkoxy and C6-10 aryloxy; preferably X ¹ represents O;

- m is 0 or 1;

- n is 0 or 1;

- p is equal to 0, 1 or 2.

2. Composition according to claim 1, in which, in the monomeric compound, R1 is hydrogen.

3. Composition according to one of the preceding claims, in which, in the monomeric compound, R2 is a hydrogen atom, and R3 is a group of formula (II).

4. Composition according to one of the preceding claims, in which, in the monomeric compound, in the group of formula (II), X is chosen from -O- and -NR- with R preferably representing a linear, branched hydrocarbon radical and / or cyclic, saturated or unsaturated, optionally comprising a hydrocarbon ring itself saturated or unsaturated, comprising 2 to 1 8, in particular 3 to 12 carbon atoms, optionally substituted by one or more groups selected from = 0, OH, NH ₂ , and halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S.

5. Composition according to one of the preceding claims, in which, in the monomeric compound, the radical R4 represents an ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclohexiyl radical , octyl, cycloctyl, decyl, cyclodecyl, dodecyl, cyclododecyl, phenyl or benzyl.

6. Composition according to one of the preceding claims, in which, in the monomeric compound, the divalent radical G is a divalent linear, branched and / or cyclic, saturated or unsaturated hydrocarbon radical, optionally comprising a hydrocarbon ring itself saturated or unsaturated, comprising in total 2 to 18, in particular 3 to 10 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ , and the halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si.

7. Composition according to one of the preceding claims, in which, in the monomeric compound, G is chosen from saturated linear or branched divalent hydrocarbon radicals optionally comprising a saturated hydrocarbon ring, comprising in total 2 to 18, in particular 3 to 10 carbon atoms.

8. Composition according to one of the preceding claims, in which, in the monomeric compound, G is chosen from the radicals ethylene, n-propylene, isopropylene (or methyl-1 ethylene and methyl-2 ethylene), n-butylene, isobutylene , pentylene in particular n-pentylene, hexylene in particular n-hexylene, cyclohexylene, heptylene, octylene, cyclooctylene, decylene, cyclodecylene, cyclohexyldimethylene in particular of formula -CH2-C ₆ H1 ₀ -CH ₂ -, dodecylene, cyclododecylene.

9. Composition according to one of the preceding claims, in which, in the monomeric compound, the polymerizable group P is chosen from one of the following formulas:

in which R 'represents H or methyl.

10. Composition according to one of the preceding claims, in which the monomeric compound corresponds to one of the following formulas, in which R is H or methyl:

11. Composition according to one of the preceding claims, in which the polymer is a homopolymer of a monomeric compound as defined in one of claims 1 to 10.

12. Composition according to one of claims 1 to 10, in which the polymer is a copolymer comprising only monomeric compounds as defined in one of claims 1 to 10.

13. Composition according to one of claims 1 to 10, in which the polymer is a copolymer comprising at least one monomeric compound as defined in one of claims 1 to 10, and at least one additional comonomer.

14. Composition according to one of claims 12 to 13, in which the polymer is a random, alternating, grafted, block or gradient copolymer.

15. Composition according to one of claims 12 to 14, in which the monomeric compound is present in an amount of 0.01 to 70% by weight relative to the weight of said polymer, in particular in an amount of 0.1% to 50 % by weight, in particular from 0.5 to 30% by weight, or even from 1 to 20% by weight, even better from 2 to 10% by weight, the additional comonomers, alone or in mixture, representing the complement to 100% in weight.

16. Composition according to one of claims 12 to 15, in which the polymer comprises at least one additional comonomer chosen from, alone or as a mixture, the following monomers:

- (ii) the (meth) acrylates of formula: CH ₃

CH ₂ = CHCOOR3 or ^{H2C = C C00R3} in which R ₃ represents:

- a linear or branched alkyl group, from 1 to 18 carbon atoms, in which there are optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group possibly also being optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (R ₄ R ₅ ), where R * and R _{5, which are} identical or different, represent a C 1 to C alkyl group or a phenyl group; in particular R3 may be a methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, isooctyl, isodecyl, dodecyl, cyo-clohexyl, t-butylcyclohexyl or stearyl group; ethyl-2-perfluorohexyl; or a hydroxyalkyl group of C1 ₄ such as 2-hydroxyethyl, 2-hydroxybutyl and 2-hydroxypropyl; or an alkoxy group (C-ι- ₄₎ alkyl (C _{_1-4)} such as methoxyethyl, ethoxyethyl and methoxypropyl, - a cycloalkyl group of C ₃ -C _12, such as an isobornyl group,

a C ₃ to C ₂₀ aryl group such as the phenyl group,

a heterocycloalkyl group (alkyl of 1 to 4 C), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups which may be optionally substituted by one or more substituents chosen from hydroxyl groups, atoms of 'halogen, and C1-4 alkyl groups, linear or branched in which there is (are) optionally intercalated (s) one or more heteroatoms chosen from O, N, S and P, said alkyl groups being able, in addition, to be optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (R4R5), where R and R5, which are identical or different, represent a C1 to C6 alkyl group This, or a phenyl group,

- R3 may also be a group - (C2H 0) _m -R ", with m = 5 to 150 and R" = H or alkyl of Ci to C ₃ 0, for example -POE-methyl or -POE-behenyl;

- (iii) (meth) acrylamides of formula:

in which R ₈ denotes H or methyl; and R ₇ and R identical or different represent:

- a hydrogen atom; or

- a linear or branched alkyl group, from 1 to 18 carbon atoms, in which there are optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group possibly also being optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (R ₄ R ₅ ), where R ₄ and R _{5, which are} identical or different, represent a C1 to C6 alkyl group or a phenyl group; in particular R3 may be a methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, isooctyl, isodecyl, dodecyl, cyo-clohexyl, t-butylcyclohexyl or stearyl group; ethyl-2-perfluorohexyl; or a C- hydroxyalkyl group such as 2-hydroxyethyl, 2-hydroxybutyl and 2-hydroxypropyl; or an alkoxy (Cι-) alkyl (Ci ^) group such as methoxyethyl, ethoxyethyl and methoxypropyl,

a C ₃ to C ₁₂ cycloalkyl group, such as the isobomyl group,

a C ₃ to C ₂ o aryl group such as the phenyl group,

a C ₄ to C ₃₀ aralkyl group (C ₁ to C 6 alkyl group) such as 2-phenylethyl, t-butylbenzyl or benzyl, a heterocyclic group of 4 to 12 members containing one or more heteroatoms chosen from O, N, and S, the cycle being aromatic or not,

a heterocycloalkyl group (alkyl of 1 to 4 C), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups which may be optionally substituted by one or more substituents chosen from hydroxyl groups, atoms of 'halogen, and C1-C4 alkyl groups, linear or branched in which there are (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P, said alkyl groups being able, in addition , be optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (FR ₅ ), where R and R _{5, which are} identical or different, represent alkyl to C _6, or a phenyl group.

(iv) the vinyl compounds of formulas: CH ₂ = CH-R ₉ , CH ₂ = CH-CH ₂ -R ₉ or CH ₂ = C (CH ₃ ) -CH ₂ -R9 in which R9 is a hydroxyl group, halogen (Cl or F), NH 2, oR ₁₀ where R 10 represents a phenyl group or an alkyl group Ci-C ₁₂ (the monomer is a vinyl or allylic ether); acetamide (NHCOCH ₃ ); an OCORn group where Ru represents an alkyl group of 2 to 12 carbons, linear or branched (the monomer is a vinyl or allyl ester); or a group chosen from:

- a linear or branched alkyl group, from 1 to 18 carbon atoms, in which there are optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group possibly also being optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (R4R ₅ ), where R ₄ and R _5, identical or different, represents a C 1 to C ₆ alkyl group or a phenyl group; a C ₃ to C ₁₂ cycloalkyl group such as isobomyl, cyclohexane,

a C ₃ to C ₂₀ aryl group such as phenyl,

a C 1 to C ₃₀ aralkyl group (C 1 to C 5 alkyl group) such as 2-phenylethyl; benzyl,

a heterocycloalkyl group (alkyl of 1 to 4 C), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups which may be optionally substituted by one or more substituents chosen from hydroxyl groups, atoms of 'halogen, and alkyl groups of 1 to 4 C linear or branched in which is (are) optionally intercalated (s) one or more heteroatoms chosen from O, N, S and P, said alkyl groups being able, in addition, to be optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F) and groups SR ₄ R5) where Ri and R2, which are identical or different, represent a C1 to C6 alkyl group, or a phenyl group.

- (v) (meth) acrylic, (meth) acrylamide or vinyl monomers containing a fluorinated or perfluorinated group, such as ethyl-perfluorooctyl or ethyl-2-perfluorohexyl (meth) acrylate;

17. The composition as claimed in claim 16, in which the additional comonomers are chosen from, alone or as a mixture, C1-C18 alkyl (meth) acrylates or C3-C12 cycloalkyl, and in particular from methyl acrylate , methyl methacrylate, isobornyl acrylate, isobornyl methacrylate, isobutyl acrylate, isobutyl methacrylate, ethyl-2-hexyl acrylate, ethyl methacrylate -2-hexyl, dodecyl acrylate, dodecyl methacrylate, stearyl acrylate, stearyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate; or alternatively acrylic acid, methacrylic acid, methacryloxypropyltris (trimethylsiloxy) silane, acryloxypropyltris (trimethylsiloxy) silane, acryloxypropylpolydimethylsiloxane and methacryloxypropylpolydimethylsiloxane.

18. Composition according to one of claims 12 to 17, in which the polymer comprises at least one additional comonomer with optical effect chosen from, alone or as a mixture, the compounds of formula (A):

in which :

- Ra1 represents a linear, branched and / or cyclic, saturated and / or unsaturated carbon radical comprising 1 to 32 carbon atoms; optionally substituted by one or more groups chosen from = 0, OH, NH ₂ , and halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S;

- Ra2 and Ra3, present on the same cycle or each on a different cycle, represent, independently of one another, a hydrogen, a halogen, or a group of formula -Xa-Ga-Pa (II), under provided that at least one of the radicals Ra2 and / or Ra3 represents a group of formula (II), in which:

- Xa is chosen from the groups -O-, -S-, -SO-, -S0 -, -NH- or -NR4- with R4 representing a linear, branched and / or cyclic, saturated and / or unsaturated carbon radical, comprising 1 to 30 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ , and the halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S; - Ga is a divalent linear, branched and / or cyclic, saturated and / or unsaturated carbon radical comprising 1 to 32 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ , and the atoms d halogen; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S;

- Pa is a polymerizable group chosen from one of the following formulas:

(,, ^la ) (lllb) (lllc) in which:

6) aryls (C6-10), the alkyl and / or aryl groups possibly also being substituted by one or more groups chosen from OH, halogen, C1-6 alkoxy and C6-10 aryloxy; and

- m is 0 or 1; n is 0 or 1; p is 0, 1 or 2.

19. Composition according to one of claims 12 to 18, in which the additional comonomer (s) are present in an amount of 30% to 99.99% by weight relative to the weight of the final polymer, in particular in an amount of 50% to 99.9% by weight, in particular from 70% to 99.5% by weight, or even from 80 to 99% by weight, even better from 90 to 98% by weight.

20. Composition according to one of the preceding claims, in which the polymer has a weight-average molecular mass (Mw) of between 50,000 and 600,000 g / mol, in particular between 10,000 and 300,000 g / mol, and even better between 20,000 and 150,000 g / mol.

21. Composition according to one of the preceding claims, in which the polymer is present, alone or as a mixture, in an amount of 0.01 to 60% by weight, preferably 0.1 to 50% by weight, in particular 1 to 25% by weight, even 3 to 15% by weight, and even better 5 to 12% by weight, relative to the total weight of the composition.

22. Composition according to one of the preceding claims, in which the physiologically acceptable medium comprises a hydrophilic medium comprising water or a water / water / organic solvent (s) mixture (s) hydrophilic (s) and / or comprises a fatty phase .

23. Composition according to one of the preceding claims, in which the fatty phase comprises waxes, pasty fatty substances, gums, lipophilic organic solvents, oils, and / or their mixtures.

24. Composition according to one of the preceding claims, further comprising a particulate phase which may comprise pigments and / or nacres and / or fillers.

25. Composition according to one of the preceding claims, comprising coloring materials chosen from water-soluble dyes and / or liposoluble dyes.

26. Composition according to one of the preceding claims, comprising at least one additional polymer such as a film-forming polymer.

27. Composition according to one of the preceding claims, comprising at least one ingredient chosen from vitamins, thickeners, gelling agents, trace elements, softeners, sequestering agents, perfumes, alkalizing or acidifying agents, preservatives, sunscreens, surfactants, antioxidants, anti-hair loss agents, anti-dandruff agents, propellants, ceramides, or mixtures thereof.

28. Composition according to one of the preceding claims, being in the form of a suspension, a dispersion in particular of oil in water thanks to vesicles; an oily solution possibly thickened or even gelled; an oil-in-water, water-in-oil, or multiple emulsion; a gel or foam; an oily or emulsified gel; a dispersion of vesicles, in particular lipid vesicles; a biphasic or multiphase lotion; a spray; loose, compact or poured powder; an anhydrous paste; a lotion, a cream, an ointment, a flexible paste, an ointment, a cast or molded solid and in particular in stick or in a cup, or else of compacted solid.

29. Composition according to one of the preceding claims, which is in the form of a product for caring for and / or making up the skin of the body or of the face, lips, nails, eyelashes, eyebrows and / or hair, a sun or self-tanning product, a hair product for the care, treatment, setting in shape, makeup or hair coloring.

30. Composition according to one of the preceding claims, which is in the form of a makeup composition, in particular a product for the complexion such as a foundation, a blusher or an eyeshadow; a lip product such as lipstick or lip care; a concealer; a blush, a mascara, an eyeliner; an eyebrow makeup product, a lip or eye pencil; a nail product such as nail polish or nail care; a body makeup product; a hair makeup product (mascara or hair spray); a composition for protecting or caring for the skin of the face, the neck, the hands or the body, in particular an anti-wrinkle composition, a moisturizing or treating composition; an anti-sun or artificial tanning composition; a hair product, in particular for coloring, maintaining the hairstyle, shaping the hair, caring for, treating or cleaning the hair, such as shampoos, gels, styling lotions, brushing lotions, fixing and styling compositions such as lacquers or spray.

31. Cosmetic process for making up or caring for keratin materials, in particular the skin of the body or face, lips, nails, eyelashes, eyebrows and / or hair, comprising the application to said materials d '' a cosmetic composition as defined in one of claims 1 to 30.

32. Monomeric compound of formula (I):

in which :

- R1 is chosen from (i) a hydrogen atom, (ii) a halogen, (iii) a linear, branched and / or cyclic, saturated and / or unsaturated carbon radical comprising 1 to 12 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ and / or optionally interrupted by one or more heteroatoms chosen from O, N, P, Si and S; (iv) a NRR 'group with R and R' being, independently of one another, a hydrogen atom or a hydro- carbon, linear, cyclic or branched, saturated in C1-6, in particular methyl, ethyl, propyl, isopropyl, n-butyl, iso-butyl, tert-butyl, pentyl or hexyl;

- X is chosen from the groups -O-, -S-, -SO-, -SO ₂ - or -NR- with R representing a linear, branched and / or cyclic, saturated and / or unsaturated carbon radical, comprising 1 to 30 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH2, and the halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S;

- P is a polymerizable group chosen from one of the following formulas:

("la) (lllb) (lllc)

in which :

6) aryls (C6-10), the alkyl and / or aryl groups possibly also being substituted by one or more groups chosen from OH, halogen, C1-6 alkoxy and C6-10 aryloxy; preferably X 'represents O;

- m is 0 or 1; - n is 0 or 1;

- p is equal to 0, 1 or 2.

33. A monomeric compound according to claim 32, in which R1 is hydrogen.

34. A monomeric compound according to one of claims 32 to 33, in which the radical R2 is a hydrogen atom and R3 is a group of formula (II).

35. Monomeric compound according to one of claims 32 to 34, in which, in said group of formula (II), X is chosen from -O- and -NR- with R preferably representing a linear, branched and / or hydrocarbon radical cyclic, saturated or unsaturated, optionally comprising a hydrocarbon ring itself saturated or unsaturated, comprising 2 to 18, in particular 3 to 12 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ , and the halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S.

36. Monomeric compound according to one of claims 32 to 35, in which the radical R is an ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclohexyl, octyl, cyclooctyl radical, decyl, cyclodecyl, dodecyl, cyclododecyl, phenyl or benzyl.

37. Monomeric compound according to one of claims 32 to 36, in which the divalent radical G is a linear, branched and / or cyclic, saturated or unsaturated divalent hydrocarbon radical, optionally comprising a hydrocarbon ring itself saturated or unsaturated, comprising in total 2 to 18, in particular 3 to 10 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ , and the halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si.

38. Monomeric compound according to one of claims 32 to 37, in which G is chosen from saturated linear or branched divalent hydrocarbon radicals optionally comprising a saturated hydrocarbon ring, comprising in total 2 to 18, in particular 3 to 10 carbon atoms .

39. Monomeric compound according to one of claims 32 to 38, in which G is chosen from the radicals ethylene, n-propylene, isopropylene (or methyl-1 ethylene and methyl-2 ethylene), n-butylene, isobutylene, pentylene in particular n-pentylene, hexylene in particular n-hexylene, cyclohexylene, heptylene, octylene, cyclooctylene, decylene, cyclodecylene, cyclohexyldimethylene in particular of formula -CH ₂ -C ₆ H ₁₀ -CH2-, dodecylene, cyclododecylene.

40. Monomeric compound according to one of claims 32 to 39, in which the polymerizable group P is chosen from one of the following formulas:

in which R 'represents H or methyl.

41. Monomeric compound according to one of claims 32 to 40, corresponding to one of the following formulas, in which R is H or methyl:

42. Polymer comprising at least one monomeric compound as defined in one of claims 32 to 41.

43. Polymer according to claim 42, characterized in that it is a homopolymer of a monomeric compound as defined in one of claims 32 to 41.

44. Polymer according to claim 42, characterized in that it is a copolymer comprising only monomeric compounds as defined in one of claims 32 to 41.

45. Polymer according to claim 42, characterized in that the monomeric compounds are each present in an amount of 0.5 to 99.5% by weight, especially 5 to 95% by weight, even 10 to 90% by weight, even better each at a rate of 30 to 70% by weight, relative to the total weight of the polymer.

46. Polymer according to claim 42, characterized in that it is a copolymer comprising at least one monomeric compound as defined in one of claims 1 to 10, and at least one additional comonomer.

47. Polymer according to claim 46, characterized in that it is a random, alternating, grafted, block or gradient copolymer.

48. Polymer according to one of claims 46 to 47, characterized in that the monomeric compound is present in an amount of 0.01 to 70% by weight relative to the weight of said polymer, in particular in an amount of 0.1% to 50% by weight, in particular from 0.5 to 30% by weight, or even from 1 to 20% by weight, even better from 2 to 10% by weight, the additional comonomers, alone or in mixture, representing the complement to 100% by weight.

49. Polymer according to one of claims 46 to 48, characterized in that it comprises at least one additional comonomer with optical effect of formula (A):

in which

- Xa is chosen from the groups -O-, -S-, -SO-, -SO ₂ -, -NH- or -NR4- with R4 representing a linear, branched and / or cyclic, saturated and / or unsaturated carbon radical , comprising 1 to 30 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH, and the halogen atoms; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S;

- Ga is a divalent linear, branched and / or cyclic, saturated and / or unsaturated carbon radical comprising 1 to 32 carbon atoms, optionally substituted by one or more groups chosen from = 0, OH, NH ₂ , and the atoms d halogen; and / or possibly interrupted by one or more heteroatoms chosen from O, N, P, Si and S;

- Pa is a polymerizable group chosen from one of the following formulas:

( ^llla ) (lllb) (lllc) in which:

- R 'represents H or a hydrocarbon radical, linear or branched, saturated in C1-6, - X' represents O, NH or NR "with R" representing a radical chosen from alkyl radicals in C1 -6, aryls in C6- 10, aryl (C6-10) alkyls (C1-6) or alkyl (C1-6) aryls (C6-10), the alkyl and / or aryl groups can also be substituted by one or more groups chosen from OH, halogen , C1-6 alkoxy and C6-10 aryloxy; and - m is 0 or 1; n is 0 or 1; p is 0, 1 or 2.

50. Polymer according to one of claims 46 to 49, characterized in that it comprises at least one additional hydrophilic comonomer, or a mixture of such comonomers, which may be present in an amount from 1 to 99.99% by weight, in particular 2-70% by weight, even better 5-50% by weight, or even 10-30% by weight, relative to the total weight of the copolymer.

51. Polymer according to one of claims 46 to 50, characterized in that it comprises at least one additional hydrophobic comonomer, or a mixture of such comonomers which may be present in an amount of 1 to 99.99% by weight, in particular 30-98% by weight, even better 50-95% by weight, or even 70-90% by weight, relative to the total weight of the copolymer.

52. Polymer according to one of claims 46 to 51, characterized in that it comprises at least one additional comonomer chosen from, alone or as a mixture, the following monomers:

- (ii) (meth) acrylates of formula: CH 3

CH ₂ = CHCOOR ₃ or ^{H2C ~ C C00R3} in which R ₃ represents: - a linear or branched alkyl group, from 1 to 18 carbon atoms, in which there are optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group possibly also being optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (R ^ Rs), where and R _The same or different represent a C1-C6 alkyl group or a phenyl group; in particular R3 may be a methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, isooctyl, isodecyl, dodecyl, cyo-clohexyl, t-butylcyclohexyl or stearyl group; ethyl-2-perfluorohexyl; or a Cι hydroxyalkyl group such as 2-hydroxyethyl, 2-hydroxybutyIe and 2-hydroxypropyl; or an alkoxy (Cι-) alkyl (CM) group such as methoxyethyl, ethoxyethyl and methoxypropyl,

a C ₃ to C ₁₂ cycloalkyl group, such as the isobornyl group,

a C ₃ to C ₂ aryl group such as the phenyl group, a C ₄ to C ₃₀ aralkyl group (C 1 to C ₈ alkyl group) such as 2-phenylethyl, t-butylbenzyl or benzyl,

a heterocycloalkyl group (alkyl of 1 to 4 C), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups which may be optionally substituted by one or more substituents chosen from hydroxyl groups, atoms of 'halogen, and C1-4 alkyl groups, linear or branched in which there is (are) optionally intercalated (s) one or more heteroatoms chosen from O, N, S and P, said alkyl groups being able, in addition, to be optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (R - R5), where R4 and R _{5, which are} identical or different, represent a group C1 to E alkyl, or a phenyl group, - R ₃ can also be a group - (C ₂ H ₄ 0) mR ", with m = 5 to 150 and R" = H or C1 to C ₃₀ alkyl, for example -POE-methyl or -POE-behenyl;

- (Ni) the (meth) acrylamides of formula:

^R8 R6 / H ~ C = C CO- N ² \ R7 in which Rs denotes H or methyl; and R7 and Re, identical or different, represent:

- a hydrogen atom; or - a linear or branched alkyl group, from 1 to 18 carbon atoms, in which there are optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group possibly also being optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (R ₄ R ₅ ), where R4 and R _{5, which are} identical or different, represents a C1-C6 alkyl group or a phenyl group; in particular R3 may be a methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, isooctyl, isodecyl, dodecyl, cyo-clohexyl, t-butylcyclohexyl or stearyl group; ethyl-2-perfluorohexyl; or hydroxyalkyl group having _{1 to} ₄ such as 2-hydroxyethyl, 2-hydroxybutyl and 2-hydroxypropyl; or an alkoxy (Cι-) alkyl (C ₁ ) group such as methoxyethyl, ethoxyethyl and methoxypropyl,

a C ₃ to C ₁₂ cycloalkyl group, such as the isobornyl group,

a C ₃ to C ₂₀ aryl group such as the phenyl group, a C to C ₃₀ aralkyl group (C 1 to C 6 alkyl group) such as 2-phenylethyl, t-butylbenzyl or benzyl,

a heterocycloalkyl group (alkyl of 1 to 4 C), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups which may be optionally substituted by one or more substituents chosen from hydroxyl groups, atoms of halogen, and C1-C4 alkyl groups, linear or branched in which there are (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P, said alkyl groups being able, in addition , be optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (R ₄ R ₅ ), where R ₄ and R _{5 are} identical or different represent a C1-C6 alkyl group, or a phenyl group.

- (iv) vinyl compounds of formulas:

CH ₂ = CH-R ₉₎ CH ₂ = CH-CH ₂ -R ₉ or CH2 = C (CH ₃ ) -CH ₂ -R9 in which R ₉ is a hydroxyl group, halogen (Cl or F), NH2, OR ₁₀ wherein R ₁₀ represents a phenyl group or an alkyl group at C ₁₂ (the monomer is a vinyl or allylic ether); acetamide (NHCOCH ₃ ); an OCORn group where Ru represents an alkyl group of 2 to 12 carbons, linear or branched (the monomer is a vinyl or allyl ester); or a group chosen from:

- a linear or branched alkyl group, from 1 to 18 carbon atoms, in which there are optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group possibly also being optionally substituted with one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F) and groups Si (R ₄ R ₅₎ wherein R and R ₅ are identical or different, represent an alkyl group -C ₆ or phenyl;

a C ₃ to C ₁₂ cycloalkyl group such as isobornyl, cyclohexane,

- a C ₃ to C ₂₀ aryl group such as phenyl, - a C ₄ to C ₃₀ aralkyl group (C ₁ to C 6 alkyl group) such as 2-phenylethyl; benzyl,

a heterocycloalkyl group (alkyl of 1 to 4 C), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups which may be optionally substituted by one or more substituents chosen from hydroxyl groups, atoms of 'halogen, and the linear or branched alkyl groups of 1 to 4 C in which there is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P, said alkyl groups being able, in addition, to be optionally substituted with one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F) and Si groups (RR ₅ ) where Ri and R _{2, which are} identical or different, represent a C1 to Ce alkyl group , or a phenyl group.

- (viii) the ethylenically unsaturated monomers comprising at least one tertiary amine function such as 2-vinylpyridine, 4-vinylpyridine, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, dimethylaminopropyl methacrylamide and salts thereof.

53. Polymer according to one of claims 46 to 52, characterized in that the additional comonomer (s) are present in an amount from 30% to 99.99% in weight relative to the weight of the final polymer, in particular in an amount of 50% to 99.9% by weight, in particular from 70% to 99.5% by weight, or even from 80 to 99% by weight, even better from 90 98% by weight.

54. Polymer according to claim 52, characterized in that the additional comonomers are chosen from, alone or as a mixture, C1-C18 alkyl (meth) acrylates or C3-C12 cycloalkyls, and in particular from acrylate methyl, methyl methacrylate, isobornyl acrylate, isobornyl methacrylate, isobutyl acrylate, isobutyl methacrylate, ethyl-2-hexyl acrylate, ethyl methacrylate -2-hexyl, dodecyl acrylate, dodecyl methacrylate, stearyl acrylate, stearyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate; or alternatively acrylic acid, methacrylic acid, methacryloxypropyltris (trimethylsiloxy) silane, acryloxypropyltris (trimethylsiloxy) silane, acryloxypropylpolydimethylsiloxane and methacryloxypropylpydydimethylsiloxane.

55. Polymer according to one of claims 42 to 54, characterized in that it has a weight-average molecular mass (Mw) of between 5000 and 600,000 g / mol, in particular between 10,000 and 300,000 g / mol, and even better between 20,000 and 150,000 g / mol.

56. Use of at least one monomeric compound as defined in one of claims 32 to 41, or of at least one polymer as defined in one of claims 42 to 55, in a composition, to give said composition of optical effects, in particular of fluorescence.