ACRYLIC POLYMER OF MALEIC ANHYDRIDE AND USE THEREOF IN COSMETICS

Abstract

The invention relates to a copolymer resulting from the polymerization of: (a) 50% to 90% by weight, of the total weight of monomers, of isobornyl (meth)acrylate, (b) 1% to 50% by weight of maleic anhydride, (c) 0% to 49% by weight of additional (meth)acrylate monomer chosen from: (i) saturated or unsaturated and linear or branched C.sub.1-C.sub.20 alkyl (meth)acrylates, the alkyl being optionally interrupted by one or more nonadjacent heteroatoms chosen from O or S or by an NR group, R being a C.sub.1-C.sub.4 alkyl group, optionally substituted by a phenyl or furfuryl group; (ii) saturated C.sub.4-C.sub.8 cycloalkyl (meth)acrylates, the cycloalkyl being optionally interrupted by O or NH.

The invention also relates to a composition comprising said copolymer in a physiologically acceptable medium.

The invention also relates to a cosmetic method for caring for or making up the skin or the lips, comprising the topical application, to the skin or the lips, of a cosmetic composition comprising said copolymer.

Claims

1. A copolymer resulting from the polymerization of: (a) 50% to 90% by weight, of the total weight of monomers, of isobornyl (meth)acrylate, (b) 1% to 50% by weight of maleic anhydride, (c) 0% to 49% by weight of additional (meth)acrylate monomer selected from the group consisting of: (i) saturated or unsaturated and linear or branched C.sub.1-C.sub.20 alkyl (meth)acrylates, the alkyl being optionally interrupted by one or more nonadjacent heteroatoms selected from the group consisting of O, S and an NR group, R being a C.sub.1-C.sub.4 alkyl group, optionally substituted by a phenyl or furfuryl group; (ii) saturated C.sub.4-C.sub.8 cycloalkyl (meth)acrylates, the cycloalkyl being optionally interrupted by O or NH.

2. The copolymer as claimed in the claim 1, which results from the polymerization of: (a) 50% to 80% by weight, of the total weight of monomers, of isobornyl (meth)acrylate, (b) 5% to 30% by weight of maleic anhydride, and (c) 15% to 30% by weight of said additional (meth)acrylate monomer.

3. The copolymer as claimed in claim 1, which results from the polymerization of: (a) 60% to 80% by weight, of the total weight of monomers, of isobornyl (meth)acrylate, (b) 5% to 25% by weight of maleic anhydride, and (c) 15% to 30% by weight of said additional (meth)acrylate monomer.

4. The copolymer as claimed in claim 1, which results from the polymerization of: (a) 50% to 80% by weight, of the total weight of monomers, of isobornyl (meth)acrylate, (b) 5% to 15% by weight of maleic anhydride, and (c) 15% to 30% by weight of said additional (meth)acrylate monomer.

5. The copolymer as claimed in claim 1, which results from the polymerization of: (a) 60% to 80% by weight, of the total weight of monomers, of isobornyl (meth)acrylate, (b) 5% to 12% by weight of maleic anhydride, (c) 18% to 30% by weight of said additional (meth)acrylate monomer.

6. The copolymer as claimed in claim 1, wherein said additional (meth)acrylate monomer is selected from the group consisting of C.sub.6-C.sub.16 alkyl (meth)acrylates.

7. The copolymer as claimed in claim 1, which results from the polymerization of: (a) 50% to 80% by weight, of the total weight of monomers, of isobornyl (meth)acrylate, (b) 5% to 30% by weight of maleic anhydride, (c) 15% to 30% by weight of C.sub.6-C.sub.16 alkyl acrylate monomer,

8. The copolymer as claimed in claim 1, which comprises isobornyl acrylate, 2-ethylhexyl acrylate and maleic anhydride.

9. The copolymer as claimed in claim 1, which has a weight-average molecular weight ranging from 5000 to 1 000 000 g/mol.

10. A composition comprising, in a physiologically acceptable medium, a polymer as claimed in claim 1.

11. The composition as claimed in claim 10, wherein the polymer is present in a content ranging from 0.1% to 10% by weight, with respect to the total weight of the composition.

12. The composition as claimed in claim 10 which comprises a hydrocarbon oil.

13. The composition as claimed in claim 10, which comprises an additive selected from the group consisting of water, fragrances, preservatives, fillers, colorants, UV-screening agents, oils, waxes, surfactants, moisturizing agents, vitamins, ceramides, antioxidants, agents for combating free radicals, polymers, thickeners, silicone oils and colorants.

14. The composition as claimed in claim 10, which is a makeup composition comprising a volatile oil and a nonvolatile oil.

15. The composition as claimed in claim 10, which is anhydrous.

16. A cosmetic method for caring for or making up the skin or the lips, comprising the topical application to the skin or the lips of a composition as claimed in claim 10.

17. The method as claimed in claim 16, which is a cosmetic method for caring for the skin, with the topical application to the skin of said composition.

18. The method as claimed in claim 17, which is intended to attenuate wrinkles.

19. The cosmetic use, as tightening agent for the skin, of the polymer as defined in claim 1.

20. The copolymer as claimed in claim 2, wherein said additional (meth)acrylate monomer is selected from the group consisting of C.sub.6-C.sub.16 alkyl (meth)acrylates.

Description

[0115] The invention is illustrated in greater detail in the following examples.

EXAMPLE 1

Isobornyl acrylate/2-ethylhexyl acrylate/maleic anhydride copolymer (70/20/10 by Weight)

[0116] 70 g of isobornyl acrylate, 20 g of 2-ethylhexyl acrylate and 10 g of maleic anhydride were introduced into a jacketed 1-litre reactor equipped with an anchor stirrer. A mixture of 70 g of isododecane and 30 g of ethyl acetate was subsequently added. The medium was brought to a temperature of 40° C. with stirring (150 revolutions/min) and bubbling with argon was carried out for 10 minutes, followed by addition of 0.5 g of initiator tert-butyl peroxy-2-ethylhexanoate Trigonox 21S (Trigonox® 21S from AkzoNobel).

[0117] The heating of the jacket was adjusted to 90° C. for 7 hours at 150 revolutions/min.

[0118] The medium was subsequently diluted with 300 g of isododecane and then concentrated by distillation in order to remove the ethyl acetate and the unreacted maleic anhydride. A 30% by weight solution of the copolymer in isododecane (yield greater than 90%) was finally obtained.

[0119] The polymer obtained has a molecular weight (Mw) of close to 200 000 g/mol.

EXAMPLE 2

Isobornyl acrylate/2-ethylhexyl acrylate/maleic anhydride copolymer (65/25/10 by Weight)

[0120] The polymer was prepared according to the procedure of example 1, using 65 g of isobornyl acrylate, 25 g of 2-ethylhexyl acrylate and 10 g of maleic anhydride.

[0121] A 30% by weight solution of the copolymer in isododecane (yield greater than 90%) was finally obtained.

[0122] The polymer obtained has a molecular weight (Mw) of close to 200 000 g/mol.

EXAMPLE 3

Isobornyl acrylate/2-ethylhexyl acrylate/maleic anhydride copolymer (75/20/5 by Weight)

[0123] The polymer was prepared according to the procedure of example 1, using 75 g of isobornyl acrylate, 20 g of 2-ethylhexyl acrylate and 10 g of maleic anhydride.

[0124] A 30% by weight solution of the copolymer in isododecane (yield greater than 90%) was finally obtained.

[0125] The polymer obtained has a molecular weight (Mw) of close to 200 000 g/mol.

EXAMPLE 4

Isobornyl acrylate/2-ethylhexyl acrylate/maleic anhydride copolymer (60/20/20 by Weight)

[0126] The polymer was prepared according to the procedure of example 1, using 60 g of isobornyl acrylate, 20 g of 2-ethylhexyl acrylate and 20 g of maleic anhydride.

[0127] A 36% by weight solution of the copolymer in isododecane (yield greater than 90%) was finally obtained.

[0128] The polymer obtained has a molecular weight (Mw) of close to 200 000 g/mol.

EXAMPLE 5

[0129] Demonstration of the Tightening Effect of the Polymers Used According to the Invention

[0130] This test consists in comparing, in vitro, the tightening power of the polymer to be evaluated, with respect to a reference tightening polymer: Hybridur® 875 polymer dispersion from Air Products (40% by weight aqueous dispersion of particles of an interpenetrated network of polyurethane and acrylic polymers). The polymer to be evaluated was deposited on a nitrile rubber strip cut from a glove sold under the reference Safeskin Nitrile Criticial No. 038846 by Dominique Dutscher SA, with a surface area of 3.5 cm.sup.2, stretched taut beforehand on a support. An aqueous solution containing the polymer to be evaluated is thus deposited on the elastomer strip, by depositing 1.8 mg (as dry matter) of polymer.

[0131] 26 μl of an aqueous solution containing 7% AM of Hybridur® 875 polymer were thus deposited on a nitrile rubber strip in order to thus obtain a reference tightening strip, and 26 μl of a solution containing 7% AM of acrylic polymer to be evaluated in an isododecane/ethanol mixture (70/30 weight/weight) were deposited on another strip. After drying at room temperature (25° C.) for 24 hours, the curving (retraction) of the strip treated with the acrylic polymer is observed in comparison with that obtained with the control (Hybridur® 875).

[0132] The tightening effect, obtained according to the protocol described above, of the polymers of examples 1 to 3 was measured. The resistance to water of the tightening effect was then also evaluated by immersing the rubber strips treated with the polymer to be evaluated in water at ambient temperature (25° C.) for 10 minutes, followed by evaluating the tightening effect after drying for 1 hour.

[0133] The following results were obtained:

TABLE-US-00001 Tightening effect Polymer Tightening after immersion tested effect in water Hybridure 875 correct correct reference Example 1 greater than greater than the reference the reference Example 2 comparable to greater than the reference the reference Example 3 comparable to greater than the reference the reference

[0134] The results obtained show that the polymers of examples 1 to 3 form a film which exhibits a good tightening effect, including after immersion in water.

EXAMPLE 6

[0135] An antiwrinkle gel having the following composition is prepared:

TABLE-US-00002 polymer of example 1 as a 7 g AM 30% by weight solution in isododecane disteardimonium hectorite/ 3 g propylene carbonate in isododecane (bentone gel ® ISDV from Elementis) Preservatives q.s. Isododecane/ethanol q.s. for 100 g (80/20 w/w)

[0136] A similar composition is also prepared using the polymer of example 2 or 3 or 4.

[0137] The composition obtained, applied to the face, makes it possible to effectively smooth out wrinkles.

EXAMPLES 7 to 14

Cosmetic Evaluation of Makeup Compositions

[0138] The 8 makeup compositions according to the invention which are described below were prepared.

[0139] Each composition was applied on a skin equivalent support made of elastomer by producing a deposited layer with a wet thickness of 100 μm, which was left to dry at ambient temperature (25° C.) for 24 hours.

[0140] The state of the film obtained was subsequently observed.

[0141] The resistance to water of the film obtained was evaluated by applying 0.5 ml of water; after 5 minutes of contact, the surface of the film was rubbed with a cotton swab and then the state of the film was observed.

[0142] The tackiness of the film and its ability to transfer or not transfer on touching the film with a finger were also evaluated.

[0143] The evaluation was carried out in the following way:

[0144] +++: cosmetic property evaluated as very effective

[0145] ++: cosmetic property evaluated as moderately effective

[0146] +: cosmetic property evaluated as not very effective

[0147] 0: cosmetic property evaluated as not effective

[0148] The following results were obtained:

TABLE-US-00003 Example 7 Example 8 Example 9 Example 10 Polymer of 20 g 20 g 20 g 20 g example 1 Pigment paste 5 g with DC 5 g with DC 5 g with black 5 g with black comprising 40% by Red 7 Red 7 iron oxide iron oxide weight of pigment in isododecane Disteardimonium 10 g 10 g 10 g 10 g hectorite (Bentone Gel ISD V from Elementis) lsododecane 65 g 45 g 65 g 45 g 2-Octyldodecanol — 20 g — 20 g Appearance Homogeneous Homogeneous Homogeneous Homogeneous of the film film film film film Resistance +++ +++ +++ +++ to water Non-tacky +++ +++ +++ +++ Transfer-resistant +++ +++ +++ +++ Example 11 Example 12 Example 13 Example 14 Polymer of 20 g 20 g 20 g 20 g example 4 Pigment paste 5 g with DC 5 g with DC 5 g with black 5 g with black comprising 40% by Red 7 Red 7 iron oxide iron oxide weight of pigment in isododecane Disteardimonium 10 g 10 g 10 g 10 g hectorite (Bentone Gel ISD V from Elementis) lsododecane 65 g 45 g 65 g 45 g 2-Octyldodecanol — 20 g — 20 g Appearance Homogeneous Homogeneous Homogeneous Homogeneous of the film film film film film Resistance +++ +++ +++ +++ to water Non-tacky +++ +++ +++ +++ Transfer-resistant +++ +++ +++ +++

[0149] The results obtained show that the polymers 1 and 4, with or without 2-octyldodecanol, form a non-tacky homogeneous film which does not transfer with the finger and which is resistant to water.