Anhydrous composition for making up keratinous materials - Patent Application 20070122997
The anhydrous composition using polyglycerol-3, dimer acid, and non-silicone oils addresses the lack of transfer resistance and film-forming properties in makeup products, enhancing colorfastness and comfort on the skin and lips.
Patent Information
- Application Number
- JP2025522694
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2022-10-19
- Publication Date
- 2025-10-20
AI Technical Summary
Existing makeup products, particularly lip products, lack effective transfer resistance and film-forming properties without using silicone-based polymers, which are often associated with a sticky or drying feel.
A solid anhydrous composition comprising polyglycerol-3, dimer acid, and C8-C30 aliphatic monoacid, along with non-volatile non-silicone oils, provides a deposit with good transfer resistance and film-forming properties.
The composition offers improved colorfastness and anti-transfer performance while maintaining a pleasant, non-sticky, and non-drying feel on the skin and lips.
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Abstract
Description
[Technical Field]
[0001] The present invention relates to an anhydrous composition for making up keratinous materials, such as the skin and lips, in particular the lips. The present invention also relates to a method for making up keratinous materials, such as the skin and lips, in particular the lips. [Background technology]
[0002] Compositions for making up the skin and / or lips are formulated to meet the need for color retention / transfer resistance.
[0003] Generally, when women use makeup products, especially lip products such as lipstick or lip gloss, they want the color of the product not to transfer easily after application and for the product to provide a pleasant sensation, such as a non-sticky and non-drying feel.
[0004] For lip makeup products with a large amount of pigment, especially lipstick or lip liquid, if the polymer with film-forming properties is not included in the formulation, consumers usually are not satisfied with their colorfastness / anti-transfer performance.In most cases, the most effective and widely used film-forming agent is silicone-based polymer, which requires a large amount of silicone oil to be dispersed.However, when oil phase is non-silicone or contains a very small amount of silicone oil, there are very few non-silicone film-forming agents available that can effectively improve colorfastness / anti-transfer performance and also have good compatibility with oil phase.
[0005] Therefore, there remains a need to obtain products for making up keratinous materials, such as skin and lips, that provide deposits with good transfer resistance and good film-forming properties. [Prior art documents] [Patent documents]
[0006] [Patent Document 1] US202110259945 [Patent Document 2] US202110259946 [Patent Document 3] US202110259930 [Patent Document 4] EP-A-847752 [Patent Document 5] EP-A-1086683 [Non-patent literature]
[0007] [Non-Patent Document 1] "The Dimer Acids: The chemical and physical properties, reactions and applications", edited by EC Leonard; Humko Sheffield Chemical, 1975, Memphis, Tenn. Summary of the Invention [Problem to be solved by the invention]
[0008] It is therefore one object of the present invention to provide a product for making up keratinous materials, such as skin and lips, which provides a deposit with good transfer resistance and good film-forming properties.
[0009] Another object of the present invention is to provide a method for making up keratinous materials, such as skin and lips, especially lips. [Means for solving the problem]
[0010] Thus, according to one aspect, the present invention provides a solid anhydrous composition for making up keratinous materials, comprising: 1) a) the following ingredients: i) at least one polyglycerol-3, and ii) at least one dimer acid, and iii) at least one C8-C 30 aliphatic monoacid wherein the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 1 mole of dimer acid, and 0.1 moles to less than 2.0 moles of fatty acid; and b) at least one non-volatile oil, preferably a non-volatile non-silicone oil H1 a polyester-containing blend containing 2) at least one wax; 3) at least one colorant selected from titanium dioxide, iron oxide, organic pigments and colorants that are soluble in the medium of the composition, and optionally 4) at least one non-volatile non-silicone oil H2, identical or different from oil H1; The present invention provides a solid anhydrous composition comprising:
[0011] Anhydrous compositions according to the present invention are particularly useful in lip products.
[0012] According to another aspect, the present invention provides a method for making up keratinous materials, such as skin and lips, especially lips, comprising the step of applying to the keratinous materials an anhydrous composition as described herein. DETAILED DESCRIPTION OF THE INVENTION
[0013] Throughout this specification, including the claims, the term "comprising" should be understood as synonymous with "comprising at least one species," unless otherwise specified. Furthermore, as used herein, the phrase "at least one species" is equivalent to the phrase "one or more."
[0014] Throughout this specification, including the claims, embodiments defined by "comprising" or the like should be understood to encompass preferred embodiments defined by "consisting essentially of" and preferred embodiments defined by "consisting of."
[0015] Other than in the operating examples, or unless otherwise indicated, all numbers expressing quantities of ingredients and / or reaction conditions should be understood to be modified in all instances by the term "about," having the meaning conventionally known in the art, e.g., within 10% of the indicated number (e.g., "about 10%" means 9%-11%, "about 2%" means 1.8%-2.2%).
[0016] Throughout this specification, including the claims, the "keratinous material" according to the present invention is preferably the skin, more preferably the lips.
[0017] In this application, contents, parts and percentages are expressed by mass unless otherwise specifically stated.
[0018] Other characteristics and advantages of the invention will become more apparent on reading the description and examples that follow.
[0019] The composition according to the present invention is in anhydrous form, which means that there is no water or that water is present in an amount that a person skilled in the art can determine as being water-free or substantially water-free. For example, the composition according to the present invention in anhydrous form may contain 3% by weight or less of water, preferably 1% by weight or less of water, based on the total weight of the composition. Preferably, the composition according to the present invention in anhydrous form does not contain a detectable amount of water, and "detectable amount" means that a certain amount can be detected by a device conventionally used in the art to measure water content.
[0020] Component 1) Polyester-containing mixture The anhydrous composition according to the present invention comprises a polyester-containing mixture as component 1), which comprises a polyester and at least one non-volatile oil.
[0021] Component a) Polyester The polyester of the present invention comprises the following components: i) at least one polyglycerol-3; ii) at least one dimer acid, and iii) at least one C8-C 30 aliphatic monoacid The reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 1 mole of dimer acid, and 0.1 mole to less than 2.0 moles of fatty acid.
[0022] Therefore, the polyesters of the present invention can be called "glycerin-based polyesters."
[0023] The term "polyglycerol-3" for the purposes of the present invention means triglycerol alone or a mixture of polyglycerols containing at least triglycerol, the triglycerol preferably being the majority of said mixture.
[0024] These are described in US202110259945, US202110259946, and US202110259930, as are their syntheses.
[0025] According to a preferred embodiment, the polyester is substantially or entirely a non-sequential reaction product.
[0026] By "substantially non-sequential reaction product" is meant that the product is produced by the substantially non-sequential reaction of reaction components i)-iii).
[0027] By "substantially non-sequential reaction of reactants i)-iii)" is meant that substantially the total content of each of the reactants i)-iii) to be reacted is added to the reaction vessel before the reaction is initiated.
[0028] In one embodiment of the present disclosure, the total content of each of the reactants i)-iii) to be reacted is added to the reaction vessel before initiating the reaction, i.e., the reaction is completely non-sequential and the polymer is a completely non-sequential reaction product of components i)-iii). In other embodiments, at least 70-100 wt.%, or 75-100 wt.%, or 80-100 wt.%, or 85-100 wt.%, or 90-100 wt.%, or 95-100 wt.%, or 97-100 wt.% of each of the reactants i)-iii) is added to the reaction vessel before initiating the reaction.
[0029] In one embodiment, the polyester is prepared by a one-step process that involves introducing all reactants into a reaction vessel and then inducing the overall statistical addition of dimer acid and isostearic acid to the polyglycerol.
[0030] Component i) Polyglycerol-3 For the purposes of the present invention, polyglycerol-3 refers to triglycerol alone or to a mixture of polyglycerols containing at least triglycerol, preferably the majority of the mixture, which has the formula H-[-OGly]3-OH, where Gly is the residue of a glycerol molecule.
[0031] The polyglycerol-3 according to the invention, in the form of a mixture of polyglycerols with triglycerols, may be any oligocondensation product of glycerol and has the formula (I): H[-O-Gly-] n -OH (I) where each Gly is independently the residue of a molecule of glycerol after removal of two hydroxyl groups, and n is an average of 2 to 10. The polyglycerol may comprise a polyglycerol having the formula:
[0032] Generally, the majority of Gly groups will be of the formula -CH2-CHOH-CH2-, although residues containing etherification at the secondary or even tertiary hydroxyl group are considered within the scope of "Gly" and may therefore also be present. Examples of oligoglycerols include diglycerol, triglycerol, tetraglycerol, pentaglycerol, hexaglycerol, heptaglycerol, octaglycerol, nonaglycerol, decaglycerol, and mixtures thereof. Particularly useful polyglycerols are those of formula (I), where n is particularly 2 to 7, more particularly 2 to 5, especially 2, 3, or 4, or mixtures of oligoglycerols within these ranges.
[0033] Examples of particularly suitable polyglycerol-3 include mixtures of oligoglycerols having the following oligomer distribution, all weight percentages being relative to the total polyglycerol content: glycerol: 0 to 30% by weight, preferably 0 to 20% by weight, more preferably 0 to 15% by weight; diglycerol: 10 to 40% by weight, preferably 15 to 35% by weight, more preferably 20 to 32% by weight; triglycerol: 10 to 65% by mass, preferably 15 to 60% by mass, more preferably 18 to 55% by mass; - tetraglycerol: 2 to 25% by weight, preferably 5 to 20% by weight, more preferably 8 to 20% by weight; - pentaglycerol: 0 to 15% by mass, preferably 0 to 10% by mass, more preferably 0 to 5% by mass; hexaglycerol: 0 to 15% by weight, preferably 0 to 10% by weight, more preferably 0 to 5% by weight; heptaglycerol: 0 to 10% by weight, preferably 0 to 5% by weight, more preferably 0 to 3% by weight; octaglycerol: 0 to 10% by weight, preferably 0 to 5% by weight, more preferably 0 to 3% by weight; nonaglycerol: 0 to 5% by weight, preferably 0 to 3% by weight, more preferably 0 to 2% by weight; Decaglycerol: from 0 to 5% by weight, preferably from 0 to 3% by weight, more preferably from 0 to 2% by weight, relative to the total weight of polyglycerol-3 in the form of a mixture.
[0034] In one embodiment, the polyglycerol-3 in the form of a mixture comprises the following oligomer distribution: Glycerol: 0 to 30% by mass Diglycerol: 15 to 40% by mass Triglycerol: 10 to 55% by mass Tetraglycerol: 2 to 25% by mass Pentaglycerol and higher components: 0 to 15% by weight, based on the total weight of polyglycerol-3 in the form of a mixture.
[0035] In one embodiment, the polyglycerol-3 in the form of a mixture comprises at least 40% by weight, or at least 45% by weight, or at least 50% by weight of a combination of diglycerol and triglycerol, relative to the total weight of the polyglycerol-3 in the form of a mixture.
[0036] In one embodiment, the polyglycerol-3 in the form of a mixture comprises at least 20% by weight, or at least 25% by weight, of diglycerol, at least 15% by weight, or at least 18% by weight, of triglycerol, at least 10% by weight, or at least 12% by weight, of tetraglycerol, all percentages by weight being relative to the total content of polyglycerol-3 in the form of a mixture.
[0037] A particularly preferred polyglycerol-3 comprises at least 25% by weight of diglycerol, at least 45% by weight of triglycerol and at least 10% by weight of tetraglycerol, relative to the total content of polyglycerol-3 in the form of a mixture.
[0038] In the form of a mixture of polyglycerols according to the present invention, any such polyglycerol-3 can be analyzed to determine its median, mean, or "average" polyglycerol number. The above example oligoglycerols, both narrow and broad distribution, can equally be referred to as "polyglycerol-3" because this is the nearest integer to the mean and / or median.
[0039] component ii) dimer acid Dimer acids useful in polyesters can be any dicarboxylic acid having at least four carbon atoms, whether linear or branched, such as, for example, dimers prepared from malonic acid, succinic acid, fumaric acid, dimethylglutaric acid, or trimethyladipic acid, and their anhydrides.
[0040] Dimeric fatty acids are particularly useful. As is known, these are mixtures of acyclic and cyclic dicarboxylic acids obtained by catalytic dimerization of unsaturated fatty acids having 12 to 22 carbon atoms.
[0041] For the preparation and use of dimer acids, as well as their physical and chemical properties, see the publication "The Dimer Acids: The Chemical and Physical Properties, Reactions and Applications," edited by E. C. Leonard; Humko Sheffield Chemical, 1975, Memphis, Tenn.
[0042] The dicarboxylic acids may also contain, to a lesser extent, trifunctional and polyfunctional carboxylic acids. The functionality of the mixture should not exceed a molar average value of 2.4.
[0043] Typically C 18 Derived from triglycerides rich in ester groups, hydrolyzed to C 18Dimer acids capable of producing unsaturated mono-acid fatty acids are preferred. This raw material can be derived from tall oil and rapeseed oil, but other natural sources can also be used, including linseed, soybean, pumpkin, and walnut. The target mono-acids used in the reaction are enriched in oleic and linoleic acid forms, as set forth in the list of fatty acids contained below. Dimerization primarily results in the dimerization of unsaturated fatty acids, although trimers are also formed. After the reaction, the product can be kept as a mixture of reaction products or can be further distilled or otherwise separated into molecular weight fractions. In one embodiment, the dimerization reaction produces a majority (at least 60% by weight, more preferably at least 75% by weight) of dimer acids (C 36 diacid), but C 54 Trimer acid is also produced (less than 30% by weight, more preferably at least 25% by weight).
[0044] In some cases, standard dimer acid Pripol 1025®, available from Croda, is used, which contains 72% by weight dimer and 19% by weight trimer acid.
[0045] In another case, the hydrogenated standard dimer acid Radiacid 0960 from Oleon was used, which contains 87% by weight of dimer and 10% by weight of trimer acid. In either case, the polymers described are characterized by higher molecular weight, more hydrophobic character, and higher viscosity than can be provided by pure low molecular weight diacids. The presence of trimer acid further increases the molecular weight and performance of these polymers.
[0046] In one embodiment, the polyesters of the present invention are prepared from at least one hydrogenated dimer acid.
[0047] In another embodiment, the polyester is a hydrogenated dimerized C 18 It is prepared from a hydrogenated dimer acid containing fatty acid, which contains an unsaturated C 18 It is obtained through the dimerization of fatty acids and subsequent hydrogenation.
[0048] In one embodiment, the hydrogenated dimer acid contains a trimer acid content in the range of about 5 to 25 weight percent, based on the total weight of the hydrogenated dimer acid.
[0049] In another embodiment, the hydrogenated dimer acid is a majority (at least 60% by weight, more preferably at least 75% by weight, but not more than 95% by weight, or better not more than 90% by weight, or even better not more than 85% by weight) hydrogenated dimer acid (C 36 diacid), C 54 It also contains hydrogenated trimer acid (less than 30%, more preferably less than 25%, but more than 5%, more preferably more than 10%, by weight).
[0050] Component iii) C8~C 30 aliphatic monoacid C8 to C useful for polyester 30 Aliphatic monoacids can include naturally occurring or refined fatty acids, such as hydrolyzed rapeseed oil, sunflower oil, etc., which contain both low and high MW chains. Useful aliphatic monoacids can be linear, branched, saturated, unsaturated, and aromatic materials, with the acidity provided by the carboxylic acid moiety.
[0051] Useful acids include caprylic acid (C8), pelargonic acid (C9), and capric acid (C 10 ), undecylic acid (C 11 ), lauric acid (C 12 ), tridecylic acid (C 13 ), myristic acid (C 14 ), pentadecylic acid (C 15 ), palmitic acid (C 16 ), margaric acid (C 17 ), stearic acid (C 18 ), isostearic acid (C 18 ), nonadecylic acid (C 19 ), arachidic acid (C 20 ), behenic acid (C 22 ) and lignoceric acid (C 24 ) are mentioned.
[0052] A comparison of stearic acid and isostearic acid shows that branching results in a high melting point and a low viscosity at room temperature in the case of isostearic acid, whereas stearic acid produces a solid material. This low viscosity can be useful in raw material handling and also in allowing esters made with this acid to retain liquid properties. Branched-chain fatty acids often contain a single methyl branch with a linear carbon chain and are naturally produced through microbial action. Isostearic acid is available as a reaction by-product in the production of the above-mentioned dimer acid.
[0053] Another route to obtain a liquid product is to use unsaturated linear and branched aliphatic monoacids. These unsaturated acids include palmitoleic acid (C16:1), vaccenic acid (C18:1), oleic acid (C18:1), elaidic acid (C18:1), linoleic acid (C18:2), linoleelaidic acid (C18:2), α-linolenic acid (C18:3), γ-linolenic acid (C18:3), stearidonic acid (C18:4), paulic acid (C20:1), gondoic acid (C20:1), dihomo-γ-linolenic acid (C20:3), mead acid (C20:3), arachidonic acid (C20:4), eicosapentaenoic acid (C20:5), erucic acid (C22:1), docosatetraenoic acid (C22:4), cervonic acid (C22:6), and nervonic acid (C24:1). As known to those skilled in the art, this designation means that the carbon chain is X carbon atoms in length and that there are Y number of double bonds in the chain.
[0054] In one embodiment, isostearic acid is preferred.
[0055] In a particularly preferred embodiment, the polyester of the present invention comprises the following components: i) at least one polyglycerol-3 in the form of a mixture comprising at least 25% by weight of diglycerol, at least 45% by weight of triglycerol, and at least 10% by weight of tetraglycerol, in each case relative to the total weight of the polyglycerol-3 in the form of the mixture; ii) at least 60% by mass of hydrogenated C36 Diacid and 5 to 25% by mass of hydrogenated C 54 at least one hydrogenated dimer acid containing triacids, in each case based on the total weight of the hydrogenated acids; and iii) Isostearic acid is a substantially or completely non-sequential reaction product of
[0056] In one embodiment, the polyester is prepared by a one-step process that involves introducing all reactants into a reaction vessel and then inducing the overall statistical addition of dimer acid and isostearic acid to the polyglycerol.
[0057] In one embodiment, it is preferred to have a total degree of esterification of the available polyglycerol hydroxyl moieties (total esterification) of 24% to 74% and a degree of esterification of the available polyglycerol hydroxyl moieties with dimer acid alone (dimer acid esterification) of 20% to 40%. More importantly, the degree of esterification with end-capping units (mono-acid esterification) is also set in this disclosure, and it is important to maintain a mono-acid esterification of 4% to 40%.
[0058] More preferably, it has an overall esterification of 28% to 57%, including 20% to 30% esterification with dimer acids and between 8% and 27% esterification with monoacids.
[0059] Even more preferred is to have an overall esterification of 33% to 48%, including 20% to 28% esterification with dimer acids and between 13% and 20% esterification with monoacids.
[0060] Even more preferred is to have an overall esterification of 24% to 74%, including 20% to 40% esterification with hydrogenated dimer acid and between 4% and 40% esterification with monoacid.
[0061] Even more preferred is to have an overall esterification of 28% to 57%, including 20% to 30% esterification with hydrogenated dimer acid and between 8% and 27% esterification with monoacid.
[0062] It is even more preferred to have an overall esterification of around 40%, including around 20% esterification with hydrogenated dimer acid and around 20% esterification with monoacid.
[0063] It is even more preferred to have an overall esterification of around 40%, including around 27% esterification with hydrogenated dimer acid and around 13% esterification with monoacid.
[0064] In one embodiment, the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 1 mole of dimer acid, and 0.2 to 1.7 moles of fatty acid.
[0065] In another embodiment, the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 0.75 moles of dimer acid, and 0.4 to 1.35 moles of isostearic acid.
[0066] In another embodiment, the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 0.7 moles of dimer acid, and 0.65 to 1 moles of isostearic acid.
[0067] In another embodiment, the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 1 mole of hydrogenated dimer acid, and 0.2 to 1.7 moles of isostearic acid.
[0068] In another embodiment, the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 0.75 moles of hydrogenated dimer acid, and 0.4 to 1.35 moles of isostearic acid.
[0069] In another embodiment, the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 0.7 moles of hydrogenated dimer acid, and 0.65 to 1 moles of isostearic acid.
[0070] In another embodiment, the reacted components are 1 mole of polyglycerol-3, 0.67 moles of hydrogenated C 36 The molar ratio is 0.67 moles of dimer acid and 0.67 moles of isostearic acid.
[0071] In a more preferred embodiment, the reacted components are 1 mole of polyglycerol-3, 0.5 moles of hydrogenated C 36 It is the molar ratio of dimer acid and 1 mole of isostearic acid.
[0072] The degree of dimer acid-polyglycerol extension and end-capping can also be controlled by adjusting the molar ratio of fatty acid end-caps and balancing the amount of polyglycerol and dimer acid, e.g., cross-linking with trimer acid results in higher viscosity.
[0073] The target viscosity of the pure polymer should be greater than 50,000 cPs and less than 5,000,000 mPa.s at 25°C.
[0074] In one preferred embodiment, the target viscosity is greater than 75,000 mPa.s and less than 2,500,000 mPa.s at 25°C.
[0075] In another preferred embodiment, the target viscosity is greater than 100,000 mPa.s and less than 2,000,000 mPa.s at 25°C.
[0076] In a more preferred embodiment, the target viscosity is greater than 1,000,000 mPa.s and less than 2,000,000 mPa.s at 25°C.
[0077] Viscosity is measured using an Anton Paar Inc. MCR3O2 Rheometer®. Two roughened or smooth 50 mm diameter plates are used to cover the polymer sample, with the gap adjusted to 0.5-1 mm, and both temperature and shear rate sweeps are performed. The polyesters of the present invention exhibit Newtonian behavior and therefore have a constant viscosity over a wide range of shear rates. The polyesters of the present disclosure also exhibit a viscosity that decreases with temperature. Therefore, viscosity measurements are reported at a precisely controlled temperature, typically at a shear rate of 1. Values are reported in mPa.s.
[0078] The polyesters of the present invention are characterized by a weight average molecular weight of greater than 2500 Da and less than 1,000,000 Da, as determined by GPC using linear polystyrene standards.
[0079] The GPC column used in these studies consisted of a phenol gel, 300 x 4.6 mm column; a continuous phase of tetrahydrofuran (THF) with an injection rate of 0.35 mL / min and a column oven temperature of 40 °C; a 50 μL injection volume; and a Wyatt refractive index RI detector. The calibration standards used were monodispersed, strictly linear polystyrene. Narrow-range polystyrene GPC calibration standards were prepared in the mobile phase with peak molecular weights of 1,290,000 Da, 560,000 Da, 65,500 Da, 28,500 Da, 10,100 Da, 1,680 Da, 580 Da, and 208 Da. Using standard methodology, the weight-average and number-average molecular weights were automatically calculated by standard GPC software.
[0080] In a preferred embodiment, the disclosed polyesters have a weight average molecular weight of greater than 4000 Da and less than 250,000 Da, as measured by GPC using linear polystyrene standards. In a more preferred embodiment, the disclosed polyesters have a weight average molecular weight of greater than 5000 Da and less than 150,000 Da, as measured by GPC using linear polystyrene standards.
[0081] In yet another embodiment, the polyesters of the present invention exhibit a combination of a weight average molecular weight of greater than 5000 Da and less than 150,000 Da, and a viscosity at 25° C. of greater than 100,000 mPa s and less than 2,000,000 mPa s, as measured by GPC using linear polystyrene standards.
[0082] In a preferred embodiment, the polyester of the present invention comprises the following components: i) at least one polyglycerol-3 in the form of a mixture comprising at least 25% by weight of diglycerol, at least 45% by weight of triglycerol, and at least 10% by weight of tetraglycerol, in each case relative to the total weight of the polyglycerol-3 in the form of the mixture; ii) at least 60% by mass of hydrogenated C 36 Diacid and 5 to 25% by mass of hydrogenated C 54 triacids, in each case based on the total mass of the hydrogenated acids, at least one hydrogenated dimer acid, and iii) Isostearic acid is a substantially or entirely non-sequential reaction product of The polyester exhibits a combination of a weight average molecular weight of greater than 5000 Da and less than 15,000 Da, as measured by GPC using linear polystyrene standards, and a viscosity of greater than 100,000 mPa.s and less than 2,000,000 mPa.s at 25°C, and the polyester is also characterized by an overall esterification of about 40%, including about 27% esterification with hydrogenated dimer acid and about 13% esterification with monoacid.
[0083] In practice, raw components contain a range of polyglycerol-3 units, as well as a range of dimer and trimer acid contents, so the above numbers can be adjusted using actual (and not theoretical) hydroxyl and carboxylic acid moieties as determined by standard methods, such as mass spectrometry, NMR, and liquid chromatography. The above esterification ranges are determined by the ratio of polyglycerol-3 and C 36Based on idealized structures of dimer acids, practical ranges may therefore vary slightly from the values given above and can be calculated based on these analytical analyses.
[0084] It is more practical to define the degree of polymerization in terms of the final acid number, which can be reliably calculated using the actual acid number determined by the raw ingredients used in light of the distribution of polyglycerol, mono-acid and poly-acid moieties present.
[0085] In one example, the initial total acid number ("AV", commonly defined as mg KOH / g total reactants) is 135 AV. This is the result of mixing 1 mole of polyglycerol-3, 0.5 moles of hydrogenated C 36 A preferred embodiment containing dimer acid and 1 mole of isostearic acid includes 68 AV for dimer acid and 67 AV for isostearic acid. All of the above preferred ratio embodiments have a corresponding initial AV that can be calculated. When AV units are reduced during the course of the polymerization reaction, this ratio gives the percent conversion of the reaction from the initial total reactive acid moieties to the final residual acid moieties. Thus, reaction completion is 1-(the ratio of final AV to initial AV).
[0086] In one embodiment, the polyesters of the present invention have a final acid number of from 0.1 mg KOH / g polymer to less than 25 mg KOH / g polymer.
[0087] In a preferred embodiment, the polyesters of the present invention have a final acid number of from 0.1 mg KOH / g polymer to less than 10 mg KOH / g polymer.
[0088] In a more preferred embodiment, the polyesters of the invention have a final acid number of from 0.1 mg KOH / g polymer to less than 5 mg KOH / g polymer.
[0089] When reaction completion is expressed as (1-final AV) / initial AV, the reaction completion of such a reactor mixture to final polymer is greater than 80%.
[0090] In a preferred embodiment, the completion of reaction of such reactor mixture to final polymer is greater than 90%.
[0091] In a more preferred embodiment, the completion of reaction of such reactor mixture to final polymer is greater than 95%.
[0092] In a more preferred embodiment, the polyester of the present invention is a copolymer of polyglycerol-3, C in a molar ratio of 1 / 0.5 / 1 as disclosed in Example 10 of US 2021 / 0259945. 36 It is the reaction product of hydrogenated dimer acid and isostearic acid.
[0093] Ingredient b) Non-volatile oil Non-volatile oils are useful as component b) to form polyester-containing blends with the polyester of component a).
[0094] Solutions of polyesters with non-volatile oils According to a particularly preferred embodiment of the present invention, the polyester-containing mixture may be in the form of an oily solution containing as components a) a polyester and b) at least one non-volatile oil.
[0095] Oil and polyester solutions of this type are described in US202110259945, US202110259946 and US202110259930.
[0096] non-volatile oil The oil present in the mixture of the present invention may be selected from the group consisting of hydrocarbon-based oils, silicone oils and mixtures thereof.
[0097] The term "oil" refers to oil at room temperature (25°C) and atmospheric pressure (760 mmHg, i.e., 10 5 Pa) refers to liquid fatty substances.
[0098] For the purposes of the present invention, the term "silicone oil" refers to an oil containing at least one Si-O group, and more particularly to an organopolysiloxane.
[0099] The term "hydrocarbon-based oil" refers to an oil containing mainly hydrogen and carbon atoms, and optionally containing one or more functional groups selected from hydroxyl, ester, ether, and carboxylic acid functional groups, i.e., the hydrocarbon-based oil is preferably a non-silicone oil.
[0100] The term "non-volatile oil" means an oil that remains on the skin or on keratin fibers at room temperature and atmospheric pressure for at least several hours and in particular has a vapor pressure of less than 2.66 Pa, preferably less than 0.13 Pa. By way of example, the vapor pressure can be measured according to the vapor pressure, static method or by the isothermal thermogravimetric effusion method (OECD Standard 104).
[0101] According to the present invention, for the purpose of use as component b), non-volatile non-silicone oils are preferred. Examples of non-volatile non-silicone oils that can be used in the present invention include: vegetable oils, such as phytostearyl esters, e.g., phytostearyl oleate, phytostearyl isostearate, and lauroyl / octyldodecyl / phytostearyl glutamate (AJINOMOTO, ELDEW PS203), diesters, for example diisopropyl sebacate, triglycerides composed of fatty acid esters of glycerol, in particular those in which the fatty acids may have a chain length ranging from C4 to C36, in particular C18 to C36 (these oils may be linear or branched, saturated or unsaturated); these oils are in particular heptanoic or octanoic acid triglycerides, shea oil, alfalfa oil, poppy seed oil, pumpkin oil, millet oil, barley oil, quinoa oil, rye oil, arrowroot oil, passion flower oil, aloe oil, sweet almond oil, peach kernel oil, peanut oil, argan oil, avocado oil, baobab oil, barrage oil, black laurel oil, Coli oil, calendula oil, camelina oil, rapeseed oil, carrot oil, safflower oil, hemp oil, rapeseed oil, cottonseed oil, coconut oil, mallow seed oil, wheat germ oil, jojoba oil, lily oil, macadamia oil, corn oil, meadowfoam oil, St. John's wort oil, monoi oil, hazelnut oil, apricot kernel oil, nut oils, olive oil, evening primrose oil, palm oil, blackcurrant seed oil, kiwi seed oil, grape seed oil, pistachio oil, pumpkin oil, winter squash oil, quinoa oil, musk rose oil, sesame oil, soybean oil, sunflower oil, castor oil and watermelon oil, and mixtures thereof, or caprylic / capric triglycerides, e.g., St.Earineries They may be those sold by the company Dubois or those sold by the company Dynamit Nobel under the names Miglyol 810®, 812® and 818®; - Linear or branched hydrocarbons of mineral or synthetic origin, such as liquid paraffin and its derivatives, e.g., C 13 ~C 16 Isoparaffins, petroleum jelly, polydecene, polybutene, hydrogenated polyisobutenes, such as Parleam or squalane; - synthetic ethers containing 10 to 40 carbon atoms, for example dicaprylyl ether; - Synthetic esters, e.g., C4-C 22 Dicarboxylic or tricarboxylic acids and C1-C 22 Esters of alcohols and mono-, di- or tricarboxylic acids with C2-C 26 Esters with di-, tri-, tetra- or pentahydroxy alcohols, examples of which include diethyl sebacate; diisopropyl sebacate; diisopropyl adipate; di-n-propyl adipate; dioctyl adipate; diisostearyl adipate; dioctyl maleate; glyceryl undecylenate; octyldodecyl stearoyl stearate; pentaerythrityl monoricinoleate; pentaerythrityl tetraisononanoate; pentaerythrityl tetrapelargonate; pentaerythrityl tetraisostearate; tetraoctane Contains pentaerythrityl acrylate;propylene glycol dicaprylate;propylene glycol dicaprate;tridecyl erucate;triisopropyl citrate;triisostearyl citrate;glyceryl trilactate;glyceryl trioctanoate;trioctyldodecyl citrate;trioleyl citrate;propylene glycol dioctanoate;neopentyl glycol diheptanoate;diethylene glycol diisononanoate;ethylene glycol distearate;diethylene glycol distearate and polyethylene glycol distearate; copolymers of polyols and diacid dimers and their esters, such as Hailuscent ISDA, or copolymers of dilinoleic acid / butanediol; aliphatic alcohols which are liquid at room temperature and contain a branched and / or unsaturated carbon chain containing from 12 to 26 carbon atoms, such as octyldodecanol, isostearyl alcohol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol or oleyl alcohol; higher fatty acids, such as oleic acid, linoleic acid or linolenic acid; - carbonates, for example, dicaprylyl carbonate; - acetate; - Citrate; - optionally partially hydrocarbon-based and / or silicone fluorooils, for example the fluorosilicone oils, fluoropolyethers and fluorosilicones described in EP-A-847752; polydimethylsiloxanes (INCI name: dimethicone) (where the R1 to R6 radicals and X are all methyl) in particular having a viscosity of 50 to 500 cSt, in particular 350 cSt, such as the commercial product sold by Wacker under the name Belsil DM 350® and by Dow Corning under the name Xiameter PMX-200 Silicone Fluid® 350 CS, and more particularly polydimethylsiloxanes (INCI name: dimethicone) having a viscosity of 50 to 150 cSt, in particular 100 cSt, such as the commercial product sold by Wacker under the name Belsil DM 100® and by Dow Corning under the name Xiameter PMX-200 Silicone Fluid 100®; phenylsilicones, such as phenyltrimethicone, phenyldimethicone, phenyltrimethylsiloxydiphenylsiloxane, diphenyldimethicone, diphenylmethyldiphenyltrisiloxane and 2-phenylethyltrimethylsiloxysilicate; and - A mixture of these.
[0102] According to a preferred embodiment, the oil is chosen from hydrocarbon-based non-volatile oils, more preferably from fatty acid triglycerides containing from 4 to 24 carbon atoms, such as caprylic / capric triglyceride.
[0103] According to a preferred embodiment, the composition according to the invention comprises polybutene, polyisobutene, hydrogenated polyisobutene, polydecene, hydrogenated polydecene, squalene, C4-C 22 Dicarboxylic or tricarboxylic acids and C1-C 22 Esters of alcohols and mono-, di- or tricarboxylic acids with C2-C 26The nonvolatile hydrocarbon oil includes one selected from esters of di-, tri-, tetra-, or pentahydroxy alcohols, and mixtures thereof.
[0104] The oily solution of the polyester of the present invention can be obtained by mixing the polyester with an organic material at around 80-100° C. The combination is then removed from the reactor and further cooled to 50-70° C. for storage.
[0105] The oily solution of the polyester of the present invention preferably contains the polyester in a concentration of 10 to 99% by mass, more preferably 30 to 90% by mass, and more particularly 50 to 80% by mass, based on the total mass of the mixture.
[0106] According to embodiments of the present invention, the non-volatile non-silicones described herein can be used as oil H1, i.e., component b), to form a polyester-containing mixture of component 1) with the polyester of component a), for example, by forming an oily solution as described herein.In addition, the non-volatile non-silicones described herein can be used with components 1), 2), and 3) as oil H2, i.e., component 4), which may be the same as or different from oil H1, to formulate an anhydrous composition.
[0107] According to certain preferred embodiments, the anhydrous compositions of the present invention comprise: a) i) at least polyglycerol-3 and ii) C 36 Hydrogenated acid dimer and iii) Isostearic acid A polyester obtained by the reaction of the above, wherein the reacted components are in a molar ratio of 1 mol of polyglycerol-3, 0.5 to 1 mol of hydrogenated dimer acid, and 0.1 mol to less than 2.0 mol of fatty acid; b) INCI name: Caprylic / Capric Triglyceride with Polyglyceryl-3 Dimer Dilinoleate Diisostearate (and) Caprylic / Capric Triglyceride It contains an oily solution containing:
[0108] Such an oily solution is commercialized by the company NOURYON under the name SOLAMAZE NATURAL® and contains 60% by weight of polymer in the active material.
[0109] The polyester-containing mixture of component 1) may be present in the anhydrous composition in an amount ranging from 0.01% to 20% by weight, more preferably from 1% to 10% by weight, and even more preferably from 1% to 5% by weight, based on the total weight of the entire anhydrous composition.
[0110] Component 2) Wax The anhydrous composition according to the invention comprises a wax as component 2).
[0111] Waxes considered in the context of the present invention are generally lipophilic compounds that are solid at room temperature (25°C), have a reversible solid / liquid state change, and have a melting point of 30°C or higher, preferably 40°C or higher, and may have a melting point of up to 200°C, in particular up to 120°C.
[0112] Waxes that may be used in the present invention include waxes of animal origin, waxes of vegetable origin, waxes of mineral origin, synthetic waxes, and various fractions of waxes of natural origin.
[0113] Animal waxes include, but are not limited to, beeswax, palm acetyl, lanolin wax, lanolin derivatives, and privet wax. Vegetable waxes include, but are not limited to, rice wax, carnauba wax, candelilla wax, ourica wax, cork fiber wax, sugarcane wax, cocoa butter, Japan wax, and urushi wax. Mineral waxes include, but are not limited to, montan wax, microcrystalline wax, paraffin, ozokerite, petroleum jelly, and ceresin. Synthetic waxes include, but are not limited to, polyethylene homopolymer and copolymer waxes, synthetic beeswax, waxes obtained by Fischer-Tropsch synthesis, and silicon waxes.
[0114] Regardless of their origin, useful waxes may be hydrocarbon waxes, such as beeswax, lanolin wax or privet wax; rice wax, carnauba wax, candelilla wax, ourica wax, espartograss wax, cork fiber wax, sugarcane wax, Japan wax and urushi wax, helianthus annuus (sunflower) seed wax; montan wax, microcrystalline wax, paraffin and ozokerite; polyethylene waxes, polymethylene waxes, waxes and waxy copolymers obtained by Fischer-Tropsch synthesis, and also esters thereof.
[0115] Linear or branched C8-C8 fatty acids obtained by catalytic hydrogenation of animal or vegetable oils 32 Waxes with aliphatic chains may also be used, as well as aliphatic esters and glycerides.
[0116] According to a particularly preferred embodiment, the waxes used in the present invention may be selected from polyethylene, synthetic waxes, paraffin, microcrystalline waxes or mixtures thereof.
[0117] The wax may be present in an amount ranging from 0.01% to 20% by weight, preferably from 0.1% to 15% by weight, more preferably from 0.5% to 10% by weight, relative to the total weight of the anhydrous composition.
[0118] Component 3) Colorant For purposes of the present invention, the term "colorant" means a compound that is capable of producing a colored optical effect when incorporated in a suitable cosmetic medium in sufficient amount.
[0119] The colorants considered in the context of the present invention may be chosen from water-soluble or water-insoluble, liposoluble (especially colorants soluble in the medium of the composition) or liposoluble organic or inorganic colorants, and materials with optical effects, and mixtures thereof.
[0120] water soluble dye Colorants useful in accordance with the present invention can include water-soluble dyes.
[0121] For the purposes of the present invention, the term "water-soluble dye" refers to any natural or synthetic, generally organic, compound that is soluble in an aqueous phase or in a water-miscible solvent and is capable of imparting color. In particular, the term "water-soluble" is intended to characterize the ability of a compound to dissolve in water to a concentration at least equal to 0.1 g / l (producing a macroscopically isotropic, transparent, colored or colorless solution), measured at 25°C. This solubility is in particular 1 g / l or more.
[0122] Suitable water-soluble dyes for use in the present invention include, in particular, synthetic or natural water-soluble dyes such as FD&C Red 4 (CI: 14700), DC Red 6 (Lithol Rubin Na; CI: 15850), DC Red 22 (CI: 45380), DC Red 28 (CI: 45410 Na salt), DC Red 30 (CI: 73360), DC Red 33 (CI: 17200), DC Orange 4 (CI: 15510), FDC Yellow 5 (CI: 19140), FDC Yellow 6 (CI: 15985), DC Yellow 8 (CI: 45350 Na salt), FDC Green 3 (CI: 42053), DC Green 5 (CI: 61570), and FDC Blue 1 (CI: 42090).
[0123] Non-limiting examples of sources of water-soluble colorants that may be used in the context of the present invention include those of natural origin, such as extracts of cochineal carmine, beetroot, grapes, carrots, tomatoes, annatto, paprika, henna, caramel and curcumin.
[0124] Thus, water-soluble colorants suitable for use in the present invention are, in particular, carminic acid, betanin, anthocyanin, enocyanin, lycopene, β-carotene, bixin, norbixin, capsanthin, capsorubin, flavoxanthin, lutein, cryptoxanthin, rubixanthin, violaxanthin, riboflavin, rhodoxanthin, canthaxanthin and chlorophyll, and mixtures thereof.
[0125] These may also be copper sulfate, iron sulfate, water-soluble sulfopolyesters, rhodamine, betaine, methylene blue, the disodium salt of tartrazine and the disodium salt of fuchsin.
[0126] Some of these water-soluble colorants are specifically approved for food use. Representative examples of these dyes that may be mentioned include, more particularly, the dyes of the carotenoid family, which are referred to by food codes E120, E162, E163, E160a-g, E150a, E101, E100, E140 and E141.
[0127] pigment Colorants useful in accordance with the present invention can include pigments, including inorganic and organic pigments.
[0128] The term "pigments" should be understood to mean white or colored inorganic (mineral) or organic particles that are insoluble in the liquid organic phase and that are intended to color and / or opacify the composition and / or the deposit produced by the composition.
[0129] The pigments may be selected from mineral pigments, organic pigments and composite pigments (i.e. pigments based on mineral and / or organic materials).
[0130] The pigments may be selected from monochrome pigments, lakes and pigments with optical effects, such as goniochromatic pigments and nacre.
[0131] The mineral pigments may be selected from metal oxide pigments, chromium oxide, iron oxide (black, yellow, red), titanium dioxide, zinc oxide, cerium oxide, zirconium oxide, chromium hydrate, manganese violet, Prussian blue, ultramarine blue, ferric blue, metal powders such as aluminum powder and copper powder, and mixtures thereof.
[0132] Organic lakes are organic pigments formed from dyes bound to a substrate.
[0133] Lakes, also known as organic pigments, may be selected from the following materials and mixtures thereof: - Cochineal carmine; - organic pigments such as azo dyes, anthraquinone dyes, indigoid dyes, xanthene dyes, pyrene dyes, quinoline dyes, triphenylmethane dyes or fluoran dyes.
[0134] Among the organic pigments that may be mentioned in particular are those known under the following names: D&C Blue No. 4, D&C Brown No. 1, D&C Green No. 5, D&C Green No. 6, D&C Orange No. 4, D&C Orange No. 5, D&C Orange No. 10, D&C Orange No. 11, D&C Red No. 6, D&C Red No. 7, D&C Red No. 17, D&C Red No. 21, D&C Red No. 22, D&C Red No. 27, D&C Red No. 28, D&C Red No. 30, D&C Red No. 31, D&C Red No. 33, D&C Red No. 34, D&C Red No. 36, D&C Violet No. 2, D&C Yellow No. 7, D&C Yellow No. 8, D&C Yellow No. 10, D&C Yellow No. 11, FD&C Blue No. 1, FD&C Green No.3, FD&C Red No.40, FD&C Yellow No.5, FD&C Yellow No.6;
[0135] The organic lakes may be insoluble sodium, potassium, calcium, barium, aluminum, zirconium, strontium or titanium salts of acid dyes, optionally containing at least one carboxylic or sulfonic acid group, such as azo, anthraquinone, indigoid, xanthene, pyrene, quinoline, triphenylmethane or fluoran dyes.
[0136] The organic lake may also be supported on an organic support, such as rosin or aluminum benzoate.
[0137] Among the organic lakes, mention may be made in particular of those known under the following names: D&C Red No. 2 Aluminum Lake, D&C Red No. 3 Aluminum Lake, D&C Red No. 4 Aluminum Lake, D&C Red No. 6 Aluminum Lake, D&C Red No. 6 Barium Lake, D&C Red No. 6 Barium / Strontium Lake, D&C Red No. 6 Strontium Lake, D&C Red No. 6 Potassium Lake, D&C Red No. 7 Aluminum Lake, D&C Red No. 7 Barium Lake, D&C Red No. 7 Calcium Lake, D&C Red No. 7 Calcium / Strontium Lake, D&C Red No. 7 Zirconium Lake, D&C Red No. 8 Sodium Lake, D&C Red No. 9 Aluminum Lake, D&C Red No. 9 Barium Lake, D&C Red No. 9 Barium / Strontium Lake, D&C Red No. 9 Zirconium Lake, D&C Red No. 10 Sodium Lake, D&C Red No. 19 Aluminum Lake, D&C Red No. 19 Barium Lake, D&C Red No. 19 Zirconium Lake, D&C Red No. 21 Aluminum Lake, D&C Red No. 21 Zirconium Lake, D&C Red No. 22 Aluminum Lake, D&C Red No. 27 Aluminum Lake, D&C Red No. 27 Aluminum / Titanium / Zirconium Lake, D&C Red No. 27 Barium Lake, D&C Red No. 27 Calcium Lake, D&C Red No. 27 Zirconium Lake, D&C Red No. 28 Aluminum Lake, D&C Red No. 30 Lake, D&C Red No. 31 Calcium Lake, D&C Red No. 33 Aluminum Lake, D&C Red No. 34 Calcium Lake, D&C Red No. 36 Lake, D&C Red No. 40 Aluminum Lake, D&C Blue No.1 Aluminum Rake, D&C Green No.3 Aluminum Rake, D&C Orange No.4 Aluminum Rake, D&C Orange No.5 Aluminum Rake, D&C Orange No.FD&C Orange No. 5 Zirconium Lake, D&C Orange No. 10 Aluminum Lake, D&C Orange No. 17 Barium Lake, D&C Yellow No. 5 Aluminum Lake, D&C Yellow No. 5 Zirconium Lake, D&C Yellow No. 6 Aluminum Lake, D&C Yellow No. 7 Zirconium Lake, D&C Yellow No. 10 Aluminum Lake, FD&C Blue No. 1 Aluminum Lake, FD&C Red No. 4 Aluminum Lake, FD&C Red No. 40 Aluminum Lake, FD&C Yellow No. 5 Aluminum Lake and FD&C Yellow No. 6 Aluminum Lake.
[0138] The pigment may also have been subjected to a hydrophobic treatment.
[0139] The hydrophobic treatment agent may be selected from silicones such as methicone, dimethicone, alkoxysilanes and perfluoroalkylsilanes; fatty acids such as stearic acid; metal soaps such as aluminum dimyristate, aluminum salt of hydrogenated tallow glutamic acid, perfluoroalkyl phosphates, perfluoroalkyl silanes, perfluoroalkyl silazanes, polyhexafluoropropylene oxide, polyorganosiloxanes containing perfluoroalkylperfluoropolyether groups and amino acids; N-acylamino acids or salts thereof; lecithin, isopropyl triisostearyl titanate, and mixtures thereof.
[0140] The N-acylamino acid may contain an acyl group containing 8 to 22 carbon atoms, such as 2-ethylhexanoyl, caproyl, lauroyl, myristoyl, palmitoyl, stearoyl, or cocoyl. Salts of these compounds may be aluminum, magnesium, calcium, zirconium, zinc, sodium, or potassium salts. The amino acid may be, for example, lysine, glutamic acid, or alanine.
[0141] The term "alkyl" referred to in the compounds cited above denotes in particular alkyl groups containing from 1 to 30 carbon atoms, preferably from 5 to 16 carbon atoms.
[0142] Hydrophobically treated pigments are described in particular in patent application EP-A-1086683.
[0143] fat soluble dye Lipid-soluble dyes, such as those soluble in the medium of the composition, may be useful. Examples include Sudan Red, DC Red 17, DC Green 6, β-carotene, soybean oil, Sudan Brown, DC Yellow 11, DC Violet 2, DC Orange 5, and quinoline yellow.
[0144] nacre For the purposes of this patent application, the term "nacre" refers to colored particles of any shape, which may or may not be pearlescent, produced in particular by certain mollusks in their shells or alternatively synthesized, and which have a color effect via optical interference.
[0145] Examples of nacre that may be mentioned include nacre pigments, such as titanium mica coated with iron oxide, mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, titanium mica coated with organic dyes, in particular of the types mentioned above, and also nacre pigments based on bismuth oxychloride.
[0146] They may also be mica particles on the surface of which at least two successive layers of metal oxides and / or organic colorants are superimposed.
[0147] The nacre may more particularly have a yellow, pink, red, bronze, orange, brown, gold and / or copper color or hue.
[0148] Examples of nacres that can be incorporated as interference pigments in the first composition include gold-colored nacres sold in particular under the names Brilliant gold 212G (Timica), Gold 222C (Cloisonne), Sparkle gold (Timica) and Monarch gold 233X (Cloisonne) by BASF; bronze-colored nacres sold in particular under the names Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona) by Merck and Super bronze (Cloisonne) by BASF; orange-colored nacres sold in particular under the names Orange 363C (Cloisonne) by BASF and Passion orange (Colorona) and Matte orange (17449) (Microna) by Merck; Nu-antique copper 340XB (Cloisonne) and Brown (17449) (Microna) by Engelhard. brown-toned nacre sold in particular under the name CL4509 (Chroma-lite); copper-toned nacre sold in particular under the name Copper 340A (Timica) by BASF; red-toned nacre sold in particular under the name Sienna fine (17386) (Colorona) by Merck; yellow-toned nacre sold in particular under the name Yellow (4502) (Chromalite) by BASF; golden-toned red nacre sold in particular under the name Sunstone G012 (Gemtone) by BASF; pink-toned nacre sold in particular under the name Tan opal G005 (Gemtone) by BASF;Mention may be made of black nacre with golden tones, sold in particular under the name Nu antique bronze 240 AB (Timica) by BASF, blue nacre sold in particular under the name Matte blue (17433) (Microna) by Merck, white nacre with silvery tones, sold in particular under the name Xirona Silver by Merck, and golden-green pink-orange nacre sold in particular under the name Indian summer (Xirona) by Merck, as well as mixtures thereof;
[0149] According to a preferred embodiment, the colorants used in the present invention are selected from metal oxide pigments, organic lakes, synthetic or natural water-soluble dyes, and mixtures thereof.
[0150] According to a preferred embodiment, the colorants used in the present invention are chosen from titanium dioxide, iron oxides, organic pigments, and colorants soluble in the medium of the composition.
[0151] According to an exemplary embodiment, the colorant used in the present invention is selected from titanium dioxide, Yellow 6 Lake, Red 7, Blue 1 Lake, or mixtures thereof.
[0152] The colorant may be present in an amount ranging from 3% to 20% by weight, preferably from 5% to 16% by weight, more preferably from 6% to 12% by weight, relative to the total weight of the composition.
[0153] additives In a particular embodiment, the anhydrous composition according to the invention may further comprise at least one additive commonly used in the field under consideration, in particular chosen from gums, anionic, cationic, amphoteric or nonionic surfactants, silicone surfactants, resins, thickeners, dispersants, antioxidants, preservatives, fragrances, neutralizing agents, antiseptics, additional cosmetic active agents such as vitamins, moisturizers, emollients or collagen protectors, and mixtures thereof.
[0154] It is routine for a person skilled in the art to adjust the nature and amount of additives present in compositions according to the invention so that the advantageous properties of the compositions used in accordance with the invention are not, or are not substantially, adversely affected by the envisaged addition.
[0155] Methods and Uses The composition according to the present invention can generally be prepared by those skilled in the art according to their general knowledge. However, it should be understood that those skilled in the art can select a preparation method based on their general knowledge, taking into account the properties of the components used, such as their solubility in the vehicle, and the intended use of one or more compositions.
[0156] According to an embodiment, the composition according to the invention can be used to treat keratinous materials, in particular the lips. This use appears as a method for caring for and / or making up said keratinous materials, in particular the lips, comprising a step of applying the composition according to the invention to said keratinous materials.
[0157] The present invention may be further illustrated by the following examples which set forth particularly advantageous embodiments.
[0158] Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the invention are approximations, the numerical values set forth in the specific examples are reported as precisely as possible. However, any numerical value inherently contains certain errors necessarily resulting from the standard deviation found in their respective measurements. The following examples are intended to illustrate the invention and, as a result, not to limit its scope. [Example]
[0159] The amounts / concentrations of ingredients in the compositions / formulations below are expressed as weight percent based on the total weight of each composition / formulation.
[0160] The main raw materials used, their trade names and suppliers are listed below. Materials without specifications were commercially available.
[0161] [Table 1]
[0162] Preparation Protocol The lipstick was prepared according to the following steps. 1) Pigment (Red 7, Red 28 Lake and / or Yellow 6 Lake) is ground with oil using a three-roll mill. 2) Weigh out the fatty phase (oils, waxes, surfactants, pastes and / or polymers) and add to the main vessel, heating the vessel to around 95°C while stirring until a homogenous mixture is achieved. 3) Add glycerin to the main container and homogenize the bulk at a strong stirring speed of 1500 rpm. 4) Add the pigment paste prepared in step 1). 5) Once the bulk is uniform, the lipstick is molded, cooled and picked.
[0163] Example A For various purposes, Ex.1 to Ex.2 according to the present invention and Comparative Examples CE.1 to CE.8
[0164] [Table 2]
[0165] Example B The composition of Example A was evaluated for color retention / anti-transfer performance according to the following procedure. - Apply the composition to the forearms three times. - Leave it for 45 minutes. - Use a tissue to cover the application area and apply constant pressure for 10 seconds. - Score from 1 to 5 according to the intensity of the color imprinted on the tissue. The lower the score, the lower the color intensity on the tissue and the better the non-transfer performance. - Average the scores of evaluations performed by at least three experienced scientists.
[0166] The scores are provided in Table 2 below.
[0167] [Table 3]
[0168] A portion of the composition of Example A was further evaluated and rated for color retention / anti-transfer performance by a consumer panel according to the following procedure. - Select 12 women between the ages of 18 and 40. - 12 users are asked to try one composition on their lips per day. - Collect their feedback after they have tested all the compositions offered.
[0169] The scores are provided in Table 3 below.
[0170] [Table 4]
[0171] Example C Following Ex.1, additional Ex.3 and Ex.4 were prepared as follows.
[0172] [Table 5]
[0173] Compositions Ex.1 to Ex.4 were evaluated for color retention / anti-transfer performance according to Example B. The results for all of Ex.1 to Ex.4 are summarized below.
[0174] [Table 6]
[0175] It has been found that the desired non-transfer performance can be achieved by using the compositions of the present invention, in particular the appropriate amount of polyglyceryl dimer dilinoleate diisostearate-(and) caprylic / capric triglyceride.
Claims
1. 1. An anhydrous composition for making up keratinous materials, comprising: 1) a) the following ingredients: i) at least one polyglycerol-3, and ii) at least one dimer acid, and iii) at least one C 8 ~C 30 aliphatic monoacid wherein the reacted components i) to iii) are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 1 mole of dimer acid, and 0.1 moles to less than 2.0 moles of fatty acid; and b) at least one non-volatile non-silicone oil H1 a polyester-containing blend containing 2) at least one wax; 3) at least one colorant selected from titanium dioxide, iron oxide, organic pigments and colorants that are soluble in the medium of the composition, and optionally 4) at least one non-volatile non-silicone oil H2, identical or different from oil H1; 1. An anhydrous composition comprising:
2. 2. The composition of claim 1, wherein the polyglycerol-3 is a triglycerol alone or a mixture of polyglycerols containing at least a triglycerol.
3. Polyglycerol-3, in the form of a mixture of polyglycerols with triglycerol, is any oligocondensation product of glycerol and has the formula (I): H[-O-Gly-] n -OH (I) where each Gly is independently the residue of a molecule of glycerol after removal of two hydroxyl groups, and n is an average of 2 to 10.
10. The composition of claim 1, comprising a polyglycerol having the formula:
4. The polyglycerol-3 comprises a mixture of oligoglycerols having the following oligomer distribution relative to the total content of polyglycerols, relative to the total mass of polyglycerol-3 in the form of a mixture: - glycerol: 0 to 30% by weight, preferably 0 to 20% by weight, more preferably 0 to 15% by weight; - diglycerol: 10 to 40% by weight, preferably 15 to 35% by weight, more preferably 20 to 32% by weight; - triglycerol: 10 to 65% by weight, preferably 15 to 60% by weight, more preferably 18 to 55% by weight; - tetraglycerol: 2 to 25% by weight, preferably 5 to 20% by weight, more preferably 8 to 20% by weight; - pentaglycerol: 0 to 15% by weight, preferably 0 to 10% by weight, more preferably 0 to 5% by weight; hexaglycerol: 0 to 15% by weight, preferably 0 to 10% by weight, more preferably 0 to 5% by weight; heptaglycerol: 0 to 10% by weight, preferably 0 to 5% by weight, more preferably 0 to 3% by weight; - octaglycerol: 0 to 10% by weight, preferably 0 to 5% by weight, more preferably 0 to 3% by weight; nonaglycerol: 0 to 5% by weight, preferably 0 to 3% by weight, more preferably 0 to 2% by weight; Decaglycerol: 0 to 5% by weight, preferably 0 to 3% by weight, more preferably 0 to 2% by weight 10. The composition of claim 1, comprising:
5. The polyglycerol-3 comprises a mixture of oligoglycerols having the following oligomer distribution relative to the total content of polyglycerols, relative to the total mass of polyglycerol-3 in the form of a mixture: Glycerol: 0 to 30% by mass Diglycerol: 15 to 40% by mass Triglycerol: 10 to 55% by mass Tetraglycerol: 2 to 25% by mass Pentaglycerol and higher components: 0-15% by weight 10. The composition of claim 1, comprising:
6. 2. The composition of claim 1, wherein the polyglycerol-3 in the form of a mixture comprises at least 40% by weight, or at least 45% by weight, or at least 50% by weight of a combination of diglycerol and triglycerol, relative to the total weight of the polyglycerol-3 in the form of a mixture.
7. 2. The composition of claim 1, wherein the polyglycerol-3 in the form of a mixture comprises at least 20% by weight, or at least 25% by weight, of diglycerol, at least 15% by weight, or at least 18% by weight, of triglycerol, and at least 10% by weight, or at least 12% by weight, of tetraglycerol, all percentages by weight being relative to the total content of the polyglycerol-3 in the form of a mixture.
8. The dimer acid is at least 60% by weight, more preferably at least 75% by weight, but not more than 95% by weight, or better still, not more than 90% by weight, or even better still, not more than 85% by weight of hydrogenated C 36 Dimer acid and less than 30% by weight, more preferably less than 25% by weight, but more than 5% by weight, more preferably more than 10% by weight of C 54 10. The composition of claim 1, wherein the hydrogenated dimer acid comprises hydrogenated trimer acid.
9. C 8 ~C 30 The aliphatic monoacid is caprylic acid (C 8 ), pelargonic acid (C 9 ), capric acid (C 10 ), undecylic acid (C 11 ), lauric acid (C 12 ), tridecylic acid (C 13 ), myristic acid (C 14 ), pentadecylic acid (C 15 ), palmitic acid (C 16 ), margaric acid (C 17 ), stearic acid (C 18 ), isostearic acid (C 18 ), nonadecylic acid (C 19 ), arachidic acid (C 20 ), behenic acid (C 22 ) and lignoceric acid (C 24 2. The composition of claim 1, wherein the compound is selected from the group consisting of:
10. Polyester contains the following components: i) at least one polyglycerol-3 in the form of a mixture comprising at least 25% by weight of diglycerol, at least 45% by weight of triglycerol, and at least 10% by weight of tetraglycerol, in each case relative to the total weight of polyglycerol-3 in the form of mixture 1; ii) at least 60% by mass of hydrogenated C 36 diacid and 5 to 25% by weight of hydrogenated C 54 at least one hydrogenated dimer acid containing triacids, in each case based on the total weight of the hydrogenated acids; and iii) Isostearic acid 10. The composition of claim 1, wherein the composition is a substantially or entirely non-sequential reaction product of:
11. 2. The composition of claim 1, wherein the reacted components i) to iii) are in the molar ratio of 1 mole of polyglycerol, 0.5 to 1 mole of dimer acid, and 0.2 to 1.7 moles of fatty acid; or 1 mole of polyglycerol-3, 0.5 to 0.75 moles of dimer acid, and 0.4 to 1.35 moles of isostearic acid; or 1 mole of polyglycerol-3, 0.5 to 0.7 moles of dimer acid, and 0.65 to 1 mole of isostearic acid.
12. 10. The composition of claim 1, wherein the polyester exhibits a weight average molecular weight, as measured by GPC using linear polystyrene standards, of greater than 5000 Da and less than 15,000 Da, in combination with a viscosity of the neat polymer at 25°C of greater than 100,000 mPa s and less than 2,000,000 mPa s.
13. the polyester having 28% to 57% by weight total esterification, including 20% to 30% by weight esterification with dimer acid and between 8% and 27% by weight esterification with monoacid; 33% to 48% by weight total esterification, including 20% to 28% by weight esterification with dimer acid and between 13% and 20% by weight esterification with monoacid; 24% to 74% by weight total esterification, including 20% to 40% by weight esterification with hydrogenated dimer acid and between 4% and 40% by weight esterification with monoacid; or 28% to 57% by weight of total esterification, including 20% to 30% by weight of esterification with hydrogenated dimer acid and between 8% and 27% by weight of esterification with monoacid. The composition of claim 1, characterized in that
14. The non-volatile non-silicone oil H1 of component b) or the non-volatile non-silicone oil H2 of component 4) are each independently a fatty acid triglyceride containing 4 to 24 carbon atoms, such as caprylic / capric triglyceride; polybutene, polyisobutene, hydrogenated polyisobutene, polydecene, hydrogenated polydecene, squalene, C 4 ~C 22 Dicarboxylic or tricarboxylic acids and C 1 ~C 22 Esters of alcohols and mono-, di- or tricarboxylic acids with C 2 ~C 26 10. The composition of claim 1, wherein the hydroxyl group is selected from the group consisting of esters with di-, tri-, tetra-, or pentahydroxy alcohols, and mixtures thereof.
15. 2. The composition of claim 1, wherein the polyester-containing mixture of component 1) is present in the anhydrous composition in an amount ranging from 0.01% to 20% by weight, more preferably from 1% to 10% by weight, and even more preferably from 1% to 5% by weight, based on the total weight of the entire anhydrous composition.
16. 2. The composition of claim 1, wherein the wax is selected from the group consisting of hydrocarbon waxes such as beeswax, lanolin wax or privet wax; rice wax, carnauba wax, candelilla wax, Euphorbia cerifera (candelilla) wax, ourica wax, espartograss wax, cork fiber wax, sugarcane wax, Japan wax and urushi wax, Helianthus annuus (sunflower) seed wax; montan wax, microcrystalline wax, paraffin and ozokerite; polyethylene wax, polymethylene wax; synthetic wax, paraffin, microcrystalline wax or mixtures thereof.
17. 2. The composition according to claim 1, wherein the wax may be present in an amount ranging from 0.01% to 20% by weight, preferably from 0.1% to 15% by weight, more preferably from 0.5% to 10% by weight, relative to the total weight of the anhydrous composition.
18. 18. Use of a composition according to any one of claims 1 to 17 in the preparation of a product for making up keratinous materials, such as the skin and lips, especially the lips.
Citation Information
Patent Citations
Biodegrable polyester for water-resistant anhydrous suncare formulation
JP2021134209A
Without rub off topical composition containing a fluorosilicon compound
EP0847752A1
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EP1086683A1
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