MXPA99008186A - Aqueous composition comprising a sulphonated polyester and a polyuret - Google Patents
Aqueous composition comprising a sulphonated polyester and a polyuretInfo
- Publication number
- MXPA99008186A MXPA99008186A MXPA/A/1999/008186A MX9908186A MXPA99008186A MX PA99008186 A MXPA99008186 A MX PA99008186A MX 9908186 A MX9908186 A MX 9908186A MX PA99008186 A MXPA99008186 A MX PA99008186A
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- Mexico
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- 239000000203 mixture Substances 0.000 title claims abstract description 101
- 229920000728 polyester Polymers 0.000 title description 9
- 229920002635 polyurethane Polymers 0.000 claims abstract description 44
- 239000004814 polyurethane Substances 0.000 claims abstract description 44
- 229920001634 Copolyester Polymers 0.000 claims abstract description 41
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 18
- 102000011782 Keratins Human genes 0.000 claims abstract description 17
- 108010076876 Keratins Proteins 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 17
- 239000002537 cosmetic Substances 0.000 claims abstract description 15
- 239000008346 aqueous phase Substances 0.000 claims abstract description 10
- 239000002245 particle Substances 0.000 claims abstract description 9
- -1 3-sulfo phenylene Chemical group 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000006185 dispersion Substances 0.000 description 18
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 12
- 210000000088 Lip Anatomy 0.000 description 12
- 238000005809 transesterification reaction Methods 0.000 description 12
- 239000003349 gelling agent Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000005886 esterification reaction Methods 0.000 description 9
- 238000006068 polycondensation reaction Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 238000006266 etherification reaction Methods 0.000 description 8
- 239000000049 pigment Substances 0.000 description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 235000019749 Dry matter Nutrition 0.000 description 5
- 210000003491 Skin Anatomy 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 239000012035 limiting reagent Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- AMXOYNBUYSYVKV-UHFFFAOYSA-M Lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- 210000004400 Mucous Membrane Anatomy 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 4
- 230000000240 adjuvant Effects 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 125000006353 oxyethylene group Chemical group 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- 210000000282 Nails Anatomy 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 210000003467 Cheek Anatomy 0.000 description 2
- 210000000720 Eyelashes Anatomy 0.000 description 2
- 210000004209 Hair Anatomy 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N Isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 239000002781 deodorant agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003020 moisturizing Effects 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 230000002335 preservative Effects 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 230000000699 topical Effects 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- YZTJKOLMWJNVFH-UHFFFAOYSA-N 2-sulfobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O YZTJKOLMWJNVFH-UHFFFAOYSA-N 0.000 description 1
- LNYYKKTXWBNIOO-UHFFFAOYSA-N 3-oxabicyclo[3.3.1]nona-1(9),5,7-triene-2,4-dione Chemical compound C1=CC(C(=O)OC2=O)=CC2=C1 LNYYKKTXWBNIOO-UHFFFAOYSA-N 0.000 description 1
- 235000011470 Adenanthera pavonina Nutrition 0.000 description 1
- 240000001606 Adenanthera pavonina Species 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L Calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- AOWKSNWVBZGMTJ-UHFFFAOYSA-N Calcium titanate Chemical compound [Ca+2].[O-][Ti]([O-])=O AOWKSNWVBZGMTJ-UHFFFAOYSA-N 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L Cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N DMA Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- WOZVHXUHUFLZGK-UHFFFAOYSA-N Dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 210000004709 Eyebrows Anatomy 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M Sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 210000001138 Tears Anatomy 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229960000314 Zinc Acetate Drugs 0.000 description 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L Zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003712 anti-aging Effects 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 108010064367 calcium titanate Proteins 0.000 description 1
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing Effects 0.000 description 1
- 230000004059 degradation Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 230000001105 regulatory Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000003385 sodium Chemical group 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 230000000475 sunscreen Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Abstract
The subject of the invention is a cosmetic or dermatological composition comprising, in an aqueous phase: i) a water-soluble or water-dispersible terephthalic copolyester oligomer comprising essentially repeating dicarboxylate units of formula (I): [- CO-A-CO-O- (CH2 -CH2O) n-] in which A represents a 1,4-phenylene, 1,3-sulfophenylene group, n ranges from 1 to 4, with at least 35% by mole of the said units of formula (I) units of formula (I) for which A represents a 1,4-phenylene group and n is equal to 1, with at least 7% by mole of the said units of formula (I) units of formula (I) for which A represents a 1,3-sulfophenylene group, the molecular weight by weight of said copolyester oligomer being below 20,000, ii) at least polyurethane particles dispersed in the aqueous phase. This composition is destined for the makeup of keratin materials
Description
AQUEOUS COMPOSITION COMPRISING A SULPHONATED POLYESTER AND A POLYURETHANE
FIELD OF THE INVENTION The present invention relates to a new non-transferable, water-resistant, topically applied smoke-free composition, "comprising a particular hydrophilic gelling agent of the sulfonated polyester type and a fumaric polyurethane, intended in particular for cosmetic and / or cosmetic fields. The invention also relates to the use of this composition for the make-up or cosmetic treatment of human keratin materials such as skin, nails, eyelashes, eyebrows, hair, or mucous membranes such as The composition of the invention can be in the form of a gel, a paste or a molten product, in particular a bar, etc. BACKGROUND OF THE INVENTION Make-up or treatment products for the skin or lips, such as foundation or red lips generally contain fatty phases such as waxes and oils, pigments and / or fillers and, optionally additives such as agent It is cosmetic or dermatological active.
They may contain gelling agents that allow REF: 31056 to obtain the desired consistency for the composition according to the application.
Brief Description of the Invention These compositions, when applied to the skin or lips, have the drawback of transferring, that is to say deposited at least in part, leaving marks, on some supports with which they can be put in contact, and particularly a glass, a cup, a cigarette, a garment or the skin. There is a mediocre persistence of the applied film, needing to regularly renew the application of the composition of background or lipstick makeup. In addition, the appearance of these unacceptable marks on blouse collars can divert some women from the use of this type of makeup. It is known from the patent application EP-A-602905 to associate volatile oils with waxes to obtain products having improved non-transfer properties. However, these products glide in their application on keratin materials, such as lips, making their application difficult to control. In addition, these products leave an impression of tightness during and after their application on the lips.
On the other hand, the compositions after application on the skin or lips can be removed on contact with water, particularly during bathing or with contact with rain or tears. It is therefore desirable to have compositions that also have good properties of remanence to water.
Description of the Invention The purpose of the present invention is to propose a new aqueous smoke composition which does not have the aforementioned drawbacks and which have particularly properties of no total transfer, of remanence to water, of absence of tightness during and after the application on the keratin materials and easy to apply. The inventors have discovered that a composition of this type could be obtained by using a particular hydrophilic gelling agent of the sulfonated polyester type and a fumaroidal polyurethane in aqueous dispersion. A composition is then obtained which leaves after application a film which exhibits a good performance, does not transfer anything, and is resistant to water. The film is particularly bright, non-adhesive and comfortable (without tightness) during and after the application of the composition on the keratin materials. The film also produces a feeling of freshness and is easy to remove make-up with the make-up removers usually used. In addition, the composition is less slippery than products without transfer containing volatile oils, thus facilitating its application on keratin materials. The subject of the present invention is therefore a novel topically applied smoke composition comprising, in an aqueous phase, a hydrophilic gelling agent of the sulfonated polyester type, characterized in that the hydrophilic gelling agent is a watersoluble or water-dispersible terephthalic copolyester oligomer and that the composition also comprises polyurethane particles dispersed in the aqueous phase. The particular gelling agents used according to the invention are water-soluble or water-dispersible terephthalic copolyester terephthalic oligomers comprising essentially repeating dicarboxylate units of formula (1):
[-CO-A-CO-O- (CH2-CH20) n-] (I) in which A represents a 1,4-phenylene, 1,3-sulfophenylene and optionally 1,3-phenylene group, n ranges from 1 and 4, - at least 35 mole% of the indicated units of formula (I) being units of formula (I) for which A represents a 1,4-phenylene group and n is equal to
1, with at least 7% by mole of the said units of formula (I) units of formula (I) for which A represents a 1,3-sulfophenylene group, the molecular weight by weight of the said oligomers being lower than 20 000, preferably less than 15 000. Preferably, at least 40 mol%, and more preferably between 40 and 90 mol% of the units of formula (I) are units of formula (I) for which A represents a 1,4-phenylene group and n is equal to l. Preferably, at least 10 mol%, more preferably between 10% and 25 mol% of the units of formula (I) are units of formula (I) for which A represents a 1,3-sulfophenylene group .
The ends of the chains of the said copolyester oligomers can be similar or different and essentially represented by the groups of formula (I '):
-CO-A-CO-O- (CH2-CH0) n-H (I ')
where A and n are as defined above. The indicated oligomers can also have at the chain ends, and in smaller amounts, groups of formulas -A-CO-OH -A-CO-OR formulas in which A is as defined above and R represents an alkyl of C1-C4. When A represents a 1,3-sulfophenylene group, it is more particularly an alkali metal sulphonate, in particular sodium or potassium sulfonate, or an ammonium sulphonate or mono-, di-, tri- or tetra-lower alkylammonium sulfonate. . By lower alkylammonium is meant preferably an ammonium of which the alkyl radical (s) is lower alkyl, preferably Cj.-C6. Preferably, it is a sodium sulfonate. The copolyester oligomer can optionally comprise up to 20 mol%, preferably from 0.5 to 5 mol% of units of formula (I) for which A represents a 1,3-phenylene group. According to a preferred embodiment of the invention, the copolyester oligomer indicated above has a molecular weight by weight ranging from 5 000 to 14 000, and more preferably from 8 000 to 10 000. Molecular masses by weight are measured by chromatography by gel permeation in dimethylacetamide containing 10"z N LiBr, at 100 ° C. The results are expressed in polystyrene equivalents The indicated copolyester oligomers can be obtained by the usual methods of preparation of the polyesters by casting, via solvent or interfacial, processes that produce reactions of esterification of diacids and diols and polycondensation of transesterification of diesters and diols and polycondensation, self-condensation of hydroxy acids, Schotten-Baumann for the realization of diols and acid chlorides and polycondensation of polymerization of lactones controlling the minimum content of ades of formula (I) for which A represents a 1,4-phenylene group and n is equal to 1, similar to the initial stoichiometric ratios of the various monomers and to the control of side reactions. A particularly interesting preparation method is that of transesterification / polycondensation and / or esterification / polycondensation via melting with the aid of a transesterification and / or esterification catalyst. The control of the structure is obtained by controlling the minimum content of units of formula (I) for which A represents a 1,4-phenylene group and n is equal to 1, similar by the initial stoichiometric ratios of the different diacid monomers and / or diesters and diol and by the use of an etherification limiting agent, limiting agent which may be a basic compound such as the aliphatic or aromatic amines or an alkali or alkaline earth metal hydroxide or acetate. The control of the molecular mass is obtained in a manner known to the person skilled in the art, through the appropriate compromise between pressure, temperature and time. The terephthalic copolyester oligomers used according to the invention can be prepared by esterification and / or transesterification / polycondensation of a monomer composition based on: - anhydride or diester terephthalic acid (Tp) - anhydride or diester sulfoisophthalic acid (Sip) - optionally acid , isophthalic anhydride or diester (Ip) - and ethylene glycol (EG) according to relative amounts corresponding to * a molar ratio (Slp) / [(Tp) + (Sip) + (Ip)] of at least 7/100, preference of at least 10/100, very particularly from 10/100 to 25/100 * a molar ratio (Ip) / [(Tp) + (Sip) + (Ip)] of 20/100 maximum, preferably 5 / 100 maximum. * a molar ratio (EG) / [(Tp) + (Sip) + (Ip)] from 2/1 to 3/1. in the presence of an esterification and / or transesterification catalyst and an etherification limiter. The terephthalic monomer (Tp) is preferably used in the form of a lower diester (dialkyl dialkyl diester), preferably dimethyl. The sulfoisophthalic monomer (Sip) is preferably used in the form of an alkali metal (mainly sodium) sulphonate of lower distether (C 1 -C 4 alkyl), preferably methyl. Particular mention may be made of dimethyl sodium-5-oxysulfonyl isophthalate. The optional isophthalic monomer (lp) is preferably used in the form of isophthalic acid. When all the "diacid" monomers are used in the form of a diester, the transesterification (exchange) operation between these "diacid" monomers and ethylene glycol monomers is carried out at a temperature greater than or equal to 130 ° C, preferably of the order of 140 to 220 ° C and very particularly in the order of 180 to 220 ° C; at this temperature the methanol (preferred case of methyl disterate) formed is removed from the reaction medium preferably by distillation. This exchange operation is carried out in the presence of a metal transesterification catalyst and an etherification limiter. The said catalyst is preferably a metal carboxylate, such as manganese acetate, zinc acetate, cobalt acetate or calcium acetate, or an organic or mineral titanate, such as butyl titanate, titanate 2, 2 ', 2"- triethyl nitrile (or titanium aminotrietanolate which also plays the role of etherification limiter) or calcium titanate The preferred catalysts are organic titanates, used in amounts of the order of at least 0.001 % by weight expressed in titanium, preferably of the order of 0.002% to 0.02% by weight of titanium based on the weight of reagents present The etherification limiting agent can be a basic compound such as aliphatic or aromatic amines (triethanolamine , guanidine carbonate, dimethylaniline, naphthyl ina ...) or an alkali or alkaline earth metal hydroxide or acetate (sodium acetate, potassium, sodium benzoate ...). ad of the order of 0.001% to 0.05% in relation to the weight of reagents present. The duration of the exchange operation is from 1 to 4 hours; it is generally of the order of 2 to 3 hours. When more than 90% of the theoretical amount of methanol has been distilled, the remaining polyol is removed by bringing the temperature of the reaction medium to 230 ° C. The polycondensation operation is preferably carried out at a temperature of the order of 230 to 280 ° C, preferably of the order of 240 to 260 ° C, in another reactor previously brought to this temperature and progressively placed under vacuum to a pressure that can reach up to lOPa; a pressure reduction of up to approximately 10 millibars lasts in the order of 40 minutes.
The polycondensation operation is carried out with removal of polyol molecules, this operation is stopped when the torque of the stirring shaft indicates a value equivalent to approximately 0.5 to 5 meters. Newton for a temperature of 250 ° C of the reaction mass and a stirring speed of 80 revolutions / minute of an anchor mobile in a 7.5 liter reactor. The vacuum is then broken with nitrogen, and the polymer is poured into an ingot mold; after cooling, the polymer shreds. When one of the "diacid" monomers is present in the form of a diacid or anhydride and the one or more is in the form of a diester (s), the indicated copolyester oligomers are obtained by first performing a transesterification operation of the diester monomers with ethylene glycol in the conditions described above, followed by an esterification operation in the medium of the diacid or anhydride monomer with ethylene glycol, then polycondensation under the conditions described above, the total amount of ethylene glycol being divided between the two operations (transesterification and esterification). If necessary, the esterification operation is carried out by adding to the reaction medium resulting from the transesterification operation, the monomer in diacid or anhydride form and ethylene glycol previously suspended, at a temperature corresponding to that of the end of the temperature of exchange; the introduction time is of the order of 1 hour. This esterification operation is carried out at a temperature of the order of 230 to 280 ° C, preferably of the order of 250 to 260 ° C, in the presence of a catalyst of the same type as that of transesterification and of an etherification limiting agent. . The operation is carried out in the presence of the same types of catalyst and etherification limiter as those used during the transesterification operation, and this in the same proportions. The reaction is carried out with the elimination of water which is transferred from the reactor at the same time as the excess polyol. This type of preparation process is particularly described in patent application WO 95/32997. The terephthalic copolyester oligomer may be present in the composition according to the invention in a content ranging from 0.5% to 40% by weight, based on the total weight of the composition. Depending on the shape sought, gelled, pasty or solid, different amounts of particular gelling agent will be used. For a solid composition, preferably from 10 to 40% by weight of particular gelling agent, more preferably from 15 to 30% by weight, will be used. For a gelled or pasty composition, preferably from 0.5 to 10% by weight of particular gellant, more preferably from 2 to 5% by weight, will be used. The polyurethane in aqueous dispersion present in the composition according to the invention can be an anionic polyurethane. This anionic character is due in particular to the presence of groups with carboxylic or sulfonic acid function in the polymer. According to the invention, one or more aqueous dispersions of one or more polyurethanes can be used. The polyurethane may be selected from polyester polyurethanes and polyether polyurethanes, and preferably from anionic polyester-polyurethanes. The size of the polyurethane particles can range between 2 and 300 nm, and preferably between 2 and 150 nm. Advantageously, the polyurethane in aqueous dispersion can be selected from among those whose hardness of a film obtained after drying, for 24 hours at 30 ° C and with 50% relative humidity, of a layer of 300 μm in thickness (before drying) ) of an aqueous dispersion at 28% dry matter of the said polyurethane particles ranges from 10 to 180 seconds, and better between 40 and 150 seconds. The hardness of the polymer film was measured according to ASTM D-43-66, or standard NF-T 30-016 (October 1981), with the help of a pendulum from Persoz. It has been observed that polyurethanes in aqueous dispersion whose polymer film has a hardness ranging between 40 and 150 seconds, as defined above, is particularly suitable when the composition is presented in solid form, particularly when the content of copolyester terephthalic oligomer it ranges between 10 and 40% by weight, relative to the total weight of the composition. In fact, these aqueous polyurethane dispersions make it possible to obtain a composition in solid form, for example a bar or a cup, without decreasing the hardness of the bar or the cup in relation to a solid analogous composition that does not contain the terephthalic copolyester ether. . The solid composition according to the invention also allows, after its application, the formation of a film on keratin materials having good non-transfer properties and water resistance. As the polyurethane usable according to the invention, mention may be made in particular of the polyester-polyurethanes sold under the names "AVALURE UR-405®", "AVALURE UR-410®", "AVALURE UR-425®", "SANCURE 2060f" by the Company GOODRICH and the polyether-polyurethanes sold under the names "SANCURE 878f" by the Company GOODRICH "NEOREZ R970®" by the ICI Company. According to the invention, the polyurethane can be present in the composition in a quantity of dry matter ranging from 1% to 40% by weight relative to the total weight of the composition, and preferably between 5% and 20% in weigh. Advantageously, the terephthalic copolyester ether and the polyurethane can be present in the composition according to the invention in an oligomer / polyurethane weight ratio ranging between 0.5 and 20, and preferably between 1 and 5. On the other hand, the composition according to The invention may contain adjuvants commonly used in cosmetic compositions, particularly topical ones. Examples of dyes, pigments, pearlescents, anti-UV agents, preservatives / thickening agents, plasticizing agents, surface-active agents, waxes, oils, perfumes, agents can be mentioned as examples of adjuvants. pH modifiers, moisturizing agents. Well, understood, the person skilled in the art will try to choose this or these possible adjuvants, and / or their quantity, in such a way that the advantageous properties of the composition according to the invention are not, or substantially, altered by the considered addition. The composition according to the invention can be used for the makeup, care or non-therapeutic cosmetic treatment of keratin and / or mucosal materials. The composition of make-up can be a product of make-up of the lips, particularly in the form of paste or bar, a foundation in the background, an eye or cheek makeup, a mask for the eyelashes or the hair, a profiler, an anti-aging - Ears, or else a body makeup composition. The cosmetic treatment or care composition can be a composition for the treatment of the face, neck, hands, body, nails or lips, a deodorant composition or also sun protection. The invention also relates to a non-therapeutic process for the treatment or make-up of keratinous and / or mucous materials consisting of applying a composition on the keratin and / or mucous materials as described above. Another subject of the invention is the use of a terephthalic copolyester ether and a polyether-urethane in aqueous dispersion, as defined above, in a cosmetic or dermatological composition to reduce or even suppress the transfer of the film of this deposited composition onto the keratin substances and / or mucous membranes and / or to suppress the deposit of marks on other support than those indicated Keratin materials and / or those indicated mucous membranes. Another subject of the invention is the use of a terephthalic copolyester oligomer and a polyurethane in aqueous dispersion as defined above in a cosmetic or dermatological composition for obtaining a film of this water-resistant and / or fresh composition and / or comfortable. The subject of the invention is also the use of a composition as defined above for obtaining a film of this water-resistant composition and / or having non-transfer and / or fresh and / or comfortable properties.
Another object of the invention is the use of a polyurethane in aqueous dispersion as defined above in a composition comprising in an aqueous phase a copolyester terephthalic oligomer as defined above to obtain a stable solid product resistant to water. Some examples illustrating the present invention without limiting it, however, will be given below. Example 1 Preparation of terephthalic copolyester ether. In a 7.5 liter stainless steel reactor, equipped with an anchor stirrer that rotates at 80 rev / min connected with a KYOWA torque meter, with a double cover for the circulation of a heat transfer fluid and a distillation column regulated by a solenoid valve were: 11.47 moles of dimethyl terephthalate 2.53 moles of sodium 5-dimethylisophthalate sulfonate 39.16 moles of ethylene glycol 54 ppm by weight of titanium, in the form of titanium aminotrietanolate as a catalyst and limiting agent of etherification. The mixture was preheated to 180 ° C. It was then brought to the temperature of 220 ° C in approximately 130 minutes, to distill more than 90% of the theoretical amount of methanol. The reaction mixture was then brought to
230 ° C in 30 minutes. When the reaction mass has reached this temperature, a suspension is introduced in 60 minutes, always at 230 ° C, whose composition is as follows: -0.5 moles of isophthalic acid -2.36 moles of terephthalic acid - 8 moles of ethylene glycol The reaction mass was then brought to a temperature of 250 ° C in 60 minutes. During the time of introduction of the mixture and during the heating time up to 250 ° C, a mixture of water and ethylene glycol is distilled without degradation. The reaction mixture is then transferred to an autoclave preheated to 250 ° C then placed under reduced pressure of 100 mbar in 22 minutes. After
2 minutes under these conditions of temperature and pressure, the reaction mass is poured and allowed to cool; The obtained copolyester has the structural characteristics described in table 1 given below, in which: * "% molar of the diacid units" corresponds to the content, in%, of each diacid or diester used in relation to the set of diacids or Diesters used. "Tp" means: telephthalic unit "lp" means: isophthalic unit "Sip" means: sulfoisophthalic unit The characteristics of the "glycol" part of the copolyesters are obtained by methanolysis of the products at 190 ° C for 16 hours followed by an analysis by the technique of vapor phase chromatography and dosed by internal contrasts. "Molar% of the diols" corresponds to the% content of the "G" oxyethylene units, the "2G" di (oxyethylene) units, the "3G" tri (oxyethylene) units and the tetra (oxyethylene) units ) "4G", in relation to the set of diole units. * "% GT / S units" corresponds to the mole% of the units of formula (I) [-CO-A-CO-O- (CH2-CH20) n-] (I) where A is 1.4 phenyl and n = l in relation to the set of units of formula (I) where A is 1, -phenylene, 1,3-sulfo phenylene and eventually
1,3-phenylene and n equals 1 to 4"% GT / S units" is calculated by the following formula: "% GT / S units = (% molar units Tp) x (% molar units G) / 100 * The molar mass of the polyesters (Mw) was determined by gel permeation chromatography (GPC) in the DMac / 100% LiBr, the results are given in polystyrene equivalents.
Example 2: A lipstick in the form of a stick was prepared with the following composition: - terephthalic copolyester ether oligomer from example 1 20% aqueous dispersion of 35% dry polystyrene-polyurethane (Avalure UR-405 from GOODRICH) 10% MA - pigments 5%
- propylene glycol 2.5%
- water csp 100%
A red lip was obtained that allows obtaining a film "without transfer" total and that resists perfectly well to water. E-arp 3: A lipstick in the form of a bar was prepared with the following composition: - terephthalic copolyester ether oligomer of example 1 20%
- aqueous dispersion of polyester-polyurethane at 49% dry matter (Avalure UR-425 from GOODRICH) 10% MA
- pigments 5%
- propylene glycol 2.5% - water csp 100%
A red lip was obtained that allows obtaining a film "without transfer" total and that resists perfectly well to water. Example 4: A profiler was prepared in the form of a gel with the following composition: - terephthalic copolyester ether oligomer of Example 1 10% aqueous dispersion of 49% dry polystyrene-polyurethane (Avalure UR-425 from GOODRICH) 8% MA - pigments 5% blacks
- propylene glycol 4%
- water csp 100% A profiler was obtained that allows obtaining a "non-transfer" make-up that perfectly resists water. Example 5: A body makeup product with the following composition was prepared: terephthalic copolyester ether oligomer from Example 1 5% aqueous dispersion of 49% dry polystyrene (Avalure UR-405 from GOODRICH) 5% MA
- pigments 5%
- propylene glycol 2.5%
- water csp 100%
It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention. Having described the invention as above, property is claimed as contained in the following:
R E I V I N D I C A C I O N S
1. Fumógeno composition of topical application, which comprises in an aqueous phase a hydrophilic gelling agent sulfonated polyester type, characterized in that: i) the sulfonated polyester-type hydrophilic gelling agent is a water-soluble or water-dispersible terephthalic copolyester terephthalic oligomer comprising essentially repeating dicarboxylate units of formula ( I):
[-CO-A-CO-O- (CH2-CH20) "-] (I)
wherein - A represents a group 1, -phenylene, 1,3-sulfophenylene and optionally 1,3-phenylene, n ranges from 1 to 4, with at least 35% by mole of the said units of formula (I) units of formula (I) for which A represents a 1,4-phenylene group and n equals
1, with at least 7% by mole of the said units of formula (I) units for which A represents a 1,3-sulfo phenylene group, and optionally up to 20 mol%, preferably up to 0, 5% to 5% by mole of formula units (I) for which A represents a 1,3-phenylene group, and the molecular mass by weight of said oligomer being below 20,000, ii) and in that the composition also comprises at least polyurethane particles dispersed in the aqueous phase. Composition according to claim 1, characterized in that the copolyester oligomer has a molecular mass by weight of less than 15 000. 3. Composition according to claim 1, characterized in that the copolyester terephthalic oligomer has a molecular mass by weight ranging between 5,000 and 14,000, and better still between 8,000 and 10,000. 4. Composition according to any one of the preceding claims, characterized in that the terephthalic copolyester ether comprises at least 40 mol% said units of formula (I) for which A represents a 1,4-phenylene group and n is equal to 1. Composition according to any one of the preceding claims, characterized in that the copolyester terephthalic oligomer comprises a 40 to 90% by mole of the indicated units of formula (I) for which A represents a 1,4-phenylene group and n is equal to 1. 6. Composition according to any one of of the preceding claims, characterized in that the terephthalic copolyester ether comprises at least 10 mol% of the units of formula (I) for which A represents a 1,3-sulfo phenylene group. Composition according to any one of the preceding claims, characterized in that the terephthalic copolyester ether comprises from 10% to 25% by mole of the said units of formula (I) for which A represents a group 1, 3-sulfo phenylene. Composition according to any one of the preceding claims, characterized in that the copolyester terephthalic oligomer comprises up to 20% by mole, and preferably between 0.5% and 5% by mole, of units of the formula ( I) for which A represents a 1,3-phenylene group. Composition according to any one of the preceding claims, characterized in that the copolyester terephthalic oligomer is present in a content ranging between 0.5% and 40% by weight, based on the total weight of the composition.
. Composition according to any one of the foregoing claims in solid form, characterized in that the copolyester terephthalic oligomer is present in a content ranging between 10% and 40% by weight, based on the total weight of the composition, and better between 15% and 30% in weight. Composition according to any one of Claims 1 to 9 in the form of a gel, characterized in that the copolyester terephthalic oligomer is present in a content ranging from 0.5% to 10% by weight, based on the total weight of the composition, and better between 2% and 5% by weight. Composition according to any one of the preceding claims, characterized in that the polyurethane is an anionic polyurethane. Composition according to any one of the preceding claims, characterized in that the polyurethane is chosen from polyester-polyurethanes and polyether-polyurethanes. Composition according to any one of the preceding claims, characterized in that the polyurethane is an anionic polyester-polyurethane. Composition according to any one of the preceding claims, characterized in that the polyurethane particles are such that the hardness of a film obtained after drying, for 24 hours at 30 ° C and at 50% relative humidity, of a 300 μm thick layer of an aqueous dispersion at 28% dry matter of said particles ranges between 10 and 180 seconds, and better between 40 and 150 seconds. Composition according to any one of the preceding claims, characterized in that the polyurethane particles have a size ranging from 2 to 300 nm. Composition according to any one of the preceding claims, characterized in that the polyurethane is present in an amount of dry matter ranging from 3% to 50% by weight relative to the total weight of the composition. Composition according to any one of the preceding claims, characterized in that the copolyester terephthalic oligomer and the polyurethane are present according to an oligomer / polyurethane weight ratio ranging between 0.5 and 20, and better between 1 and 5. 19 Composition according to any one of the preceding claims, characterized in that the composition is a cosmetic or dermatological composition. Composition according to any one of the preceding claims, characterized in that it comprises at least one adjuvant selected from the group consisting of dyes, pigments, pearlescents, anti-UV agents, preservatives, thickening agents , plasticizing agents, surfactants, waxes, oils, perfumes, pH modifying agents, moisturizing agents. Composition according to any one of the preceding claims, characterized in that it is presented in the form of a make-up composition or a cosmetic treatment of the keratin and / or mucosal materials. Composition according to any one of the preceding claims, characterized in that the composition is presented in the form of a lip makeup product, a foundation makeup, an eye or cheek make-up, a mask , of a profiler, of an anti-dark circles, of a composition of body make-up, of a composition for the treatment of the face, of the neck, of the hands, of the body, of the nails or of the lips, of a composition deodorant, of a sunscreen composition. 23. Non-therapeutic method of make-up or treatment of keratin and / or mucosal materials, characterized in that a composition according to one of claims 1 to 22 is applied to the keratin and / or mucous materials. Use of a water-soluble or water-dispersible terephthalic copolyester terephthalic oligomer comprising essentially repeating dicarboxylate units of formula (I):
[-CO-A-CO-O- (CH2-CH20) n-] (I)
wherein A represents a 1, 4-phenylene, 1,3-sulfophenylene and optionally 1,3-phenylene group, n ranges from 1 to 4, with at least 35% by mole of the said units of formula (I) units of formula (I) for which A represents a 1,4-phenylene group and n equals
1, with at least 7% by mole of the said units of formula (I) units of formula (I) for which A represents a 1,3-sulfo phenylene group, and optionally up to 20% by moles, of preferably up to 0.5% to 5% by mole of formula units (I) for which A represents a 1,3-phenylene group, and the molecular weight by weight of said oligomer being below 20,000, and a polyurethane in aqueous dispersion in aqueous dispersion, in a cosmetic or dermatological composition to diminish, even suppress, the transfer of the film of this deposited composition onto the keratin and / or mucosal materials, and / or to suppress the deposition of marks on other support other than the indicated keratin materials and / or the indicated mucous membranes. 25. Use of a water-soluble or water-dispersible terephthalic copolyester terephthalic oligomer comprising essentially repeating dicarboxylate units of formula (I):
[-CO-A-CO-O- (CH2-CH0) n-] (I)
wherein - A represents a 1,4-phenylene, 1,3-sulfophenylene and optionally 1,3-phenylene group, n ranges from 1 to 4, with at least 35% by mole of the said units of formula (I ) units of formula (I) for which A represents a 1,4-phenylene group and n is equal to 1, with at least 7% by mole of the indicated units of formula (I) units for which A represents a group 1,3-sulfo phenylene, and optionally up to 20 mol%, preferably up to 0.5% to 5 mol% of formula units (I) for which A represents a 1,3-phenylene group, and the molecular weight by weight of said oligomer being below 20,000, and of a polyurethane in aqueous dispersion, in a cosmetic or dermatological composition for obtaining a film of this water-resistant and / or fresh and / or comfortable composition. 26. Use of a composition according to any one of claims 1 to 22, for obtaining a film of this water-resistant composition and / or having non-transfer and / or fresh and / or comfortable properties.
27. Use of a polyurethane in aqueous dispersion in a composition comprising, in an aqueous phase, a water-soluble or water-dispersible terephthalic copolyester terephthalic oligomer comprising essentially repeating dicarboxylate units of formula (I):
[-CO-A-CO-O- (CH2-CH20) n-] (I)
wherein - A represents a 1,4-phenylene, 1,3-sulfophenylene and optionally 1,3-phenylene group, n ranges from 1 to 4, with at least 35% by mole of the said units of formula (I ) units of formula (I) for which A represents a 1,4-phenylene group and n is equal to
1, with at least 7% by mole of the said units of formula (I) units of formula (I) for which A represents a 1,3-sulfo phenylene group, and optionally up to 20% by moles, of preferably up to 0.5% to 5% by mole of formula units (I) for which A represents a 1,3-phenylene group, and the molecular weight by weight of said oligomer being less than 20,000, to obtain a stable solid product resistant to water.
Claims (3)
- The subject of the invention is a cosmetic or dermatological composition comprising, in an aqueous phase: i) a water-soluble or water-dispersible terephthalic copolyester terephthalic oligomer comprising essentially repeating dicarboxylate units of formula (I):
- [-CO-A-CO-O- (CH2-CH20) "-] (I) wherein A represents a 1, 4-phenylene, 1,3-sulfophenylene group, n ranges from 1 to 4, - at least 35% by mole of said units of formula (I) being units of formula (I) for which A represents a 1,4-phenylene group and n is equal to 1, with at least 7% by mole of the said units of formula (I) units of formula (I) for which A represents a group 1,
- 3-sulfo phenylene, the molecular weight by weight of said copolyester oligomer being below 20,000, ii) at least polyurethane particles dispersed in the aqueous phase. This composition is intended for the makeup of keratin materials.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9811362 | 1998-09-11 |
Publications (1)
Publication Number | Publication Date |
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MXPA99008186A true MXPA99008186A (en) | 2000-08-01 |
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