Aqueous cosmetic or dermatological composition comprising merocyanine and water-soluble UV screening agent
By adding a water-soluble UV shielding agent to the cosmetic composition, the problems of solubility and photostability of cyanine in the aqueous phase are solved, achieving high shielding efficiency and transparent, comfortable skin protection effects in the long UVA range.
Patent Information
- Application Number
- CN202480040229.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-06-16
- Filing Date
- 2024-05-27
- Publication Date
- 2026-01-13
AI Technical Summary
Existing UV shielding agents have insufficient solubility and photostability in aqueous and lipid phases, resulting in poor shielding effect of cosmetic compositions in the long UVA radiation range. Furthermore, high content of shielding agents leads to instability and unpleasant texture, making it difficult to achieve transparent and comfortable skin protection.
Adding small amounts of water-soluble UV-blocking agents, especially benzene-1,4-bis(3-methylene-10-camphorsulfonic acid) and benzoxazole compounds, to cosmetic compositions improves the water solubility of anthocyanins and combines with organic UV-blocking agents to form stable transparent compositions.
It significantly improves the solubility and photostability of cyanide in the aqueous phase, ensuring high shielding efficiency of the composition in the 280-400 nm wavelength range, providing a transparent and non-greasy skin protection effect, while maintaining the stability and comfort of the composition.
Smart Images

Figure CN121335690A_ABST
Abstract
Description
[0001] The present invention relates to an aqueous cosmetic or dermatological composition comprising at least one merocyanine of formula (3) (which will be defined in detail hereinafter) and at least one water-soluble UV-screening agent. TECHNICAL FIELD
[0002] It is known that radiation with a wavelength between 280 nm and 400 nm enables tanning of the human epidermis and that radiation with a wavelength between 280 and 320 nm, known under the name UV-B rays, can jeopardize the progress of natural tanning. Exposure also easily induces damage to the biomechanical properties of the epidermis, which is reflected in the appearance of wrinkles, leading to premature aging of the skin.
[0003] It is also known that UV-A rays with a wavelength between 320 and 400 nm penetrate more deeply into the skin than UV-B rays. UV-A rays cause immediate and persistent darkening of the skin. Under normal circumstances, even short daily exposure to UVA rays can lead to degradation of the collagen and elastin fibers, which is reflected in the altered microrelief of the skin, the appearance of wrinkles and uneven pigmentation (freckles, or uneven skin tone).
[0004] Protection against UVA and UVB radiation is therefore necessary. An effective photoprotective product must protect against both UVA and UVB radiation.
[0005] To date, numerous photoprotective compositions for overcoming the effects caused by UVA and / or UVB radiation have been proposed. These photoprotective compositions generally contain organic UV-screening agents and / or inorganic UV-screening agents, which act by absorbing, reflecting or scattering UV radiation according to their own chemical nature and according to their own properties. They generally contain a mixture of liposoluble organic screening agents and / or water-soluble UV-screening agents combined with metal oxide pigments such as titanium dioxide or zinc oxide.
[0006] Moreover, most organic UV-screening agents consist of aromatic compounds that absorb in the wavelength range between 280 and 370 nm. In addition to their ability to screen solar radiation, the photoprotective compounds desired must also have good cosmetic properties, good solubility in the usual solvents and in particular in fatty substances such as oils or water, and also good photostability, alone or in combination with other UV-screening agents. They must also be colorless or at least have a cosmetically acceptable color for the consumer.
[0007] One of the known main drawbacks of these compositions to date is the insufficient efficacy of these screening systems against UV radiation and in particular against long UVA radiation with wavelengths greater than 370 nm, the aim being to control photo-induced pigmentation and its development by systems that screen out UV radiation over the entire UV spectrum.
[0008] Among all the compounds recommended for this purpose, a favourable family of UV screening agents consisting of carbonized merocyanine derivatives has been proposed, described in patent US 4 195 999, application WO 2004 / 006878 and document IP COM Publ. 4(4), 16, ref. IPCOM000011179D (published 04 / 03 / 2004). These compounds exhibit very good screening properties in the long UVA radiation range, but exhibit only slightly satisfactory solubility in usual solvents, both in aqueous and in fatty phases, and some merocyanines exhibit unsatisfactory photostability.
[0009] In order to find other merocyanines with better solubility in usual solvents and better photostability, application WO 2013 / 011094 has proposed merocyanines comprising polar groups consisting of hydroxyl and ether functions, which exhibit good long UVA screening efficacy. However, the solubility of these particular merocyanines is still not entirely satisfactory and often requires lengthy formulation processes. Furthermore, the large amounts of solvent required in order to solubilize merocyanines of this type can lead to cosmetic dissatisfaction, such as tackiness and greasy effect on application.
[0010] There is therefore still a need to improve the solubility of these merocyanines in cosmetic compositions, in particular in photoprotection formulations, both in aqueous and in fatty phases, while still obtaining good cosmetic properties.
[0011] Furthermore, there is also still a need to improve the solubility of merocyanines in the presence of organic screening agents. Indeed, the addition of additional screening agents can destabilize compositions comprising merocyanines.
[0012] UV screening agents are most often delivered as anti-UV active agents in an oily and / or aqueous phase and are generally provided in the form of emulsions or gels.
[0013] It is also known that, in order to achieve high levels of screening efficiency, high contents of screening agents are required.
[0014] However, high contents of UV-screening agents are not easy to produce in themselves compositions with stable and pleasant textures.
[0015] Therefore, formulations with high opacity often have unpleasant or even offensive sensory aspects that mask the freshness and comfort of the formulation. In particular, the weaknesses of light-protective formulations with high protection factors can often be a strong greasy feeling, a lack of lightness in the resulting texture, and a white appearance upon application, making them not invisible on the skin.
[0016] Furthermore, the introduction of high concentrations of UV-masking agents often leads to instability issues. This instability can sometimes even result in phase separation of the emulsion and / or viscosity loss of the composition, rendering the formulation inefficient or even unusable.
[0017] To overcome the aforementioned undesirable effects, and especially to achieve a refreshing effect upon application and an invisible effect on the skin, water-based formulations have been considered. However, these water-based compositions containing UV-masking agents are typically sticky and therefore uncomfortable.
[0018] Therefore, there is a need for a water-based cosmetic or dermatological composition that has good long-term UVA shielding efficiency, good cosmetic properties, and is completely stable and uniform, meaning it does not undergo delamination.
[0019] There is also a need for an aqueous photoprotective composition that has good shielding efficiency across the entire wavelength spectrum between 280 and 400 nm, good cosmetic properties, and is completely stable and homogeneous, meaning it does not undergo delamination.
[0020] A water-based cosmetic or dermatological composition is also needed, which has good long-term UVA blocking efficiency and is, in addition, transparent. Furthermore, a cosmetic or dermatological composition is needed that remains transparent even after application to the skin.
[0021] In particular, there is still a need for an aqueous cosmetic or dermatological composition that has good shielding efficiency between 370 nm and 400 nm and may have a high level of UV protection across the entire wavelength spectrum between 280 nm and 400 nm, good cosmetic properties upon application, especially easy application, without an oily or sticky finish on the skin, especially after drying, and a pleasant sensory effect achieved particularly through a smooth feel upon application.
[0022] The purpose of this invention is to provide new cosmetic or dermatological compositions that solve these problems.
[0023] The applicant has unexpectedly discovered that the addition of at least one water-soluble masking agent (which is not a solvent and must itself be soluble in water) can significantly increase the water solubility of the aforementioned anthocyanins.
[0024] This allows these specific anthocyanins to be dissolved in essentially water-based sunscreens without the addition of additional solvents.
[0025] This discovery forms the basis of the present invention. Summary of the Invention
[0026] Therefore, according to one aspect of the subject matter of the invention, an aqueous cosmetic or dermatological composition is now proposed, the composition comprising:
[0027] a) at least one cyanide of formula (3), which will be defined in detail below, in an amount less than 3% by weight relative to the total weight of the composition; and
[0028] b) At least one water-soluble UV shielding agent.
[0029] Therefore, the water solubility of cyanide is improved in the presence of at least one water-soluble UV masking agent.
[0030] The applicant has unexpectedly discovered that by using at least one water-soluble UV masking agent, even in the presence of other organic UV masking agents, the solubility of these anthocyanins in the aqueous phase can be significantly improved.
[0031] The applicant has also discovered that using a combination of at least one such anthocyanin with at least one water-soluble UV shielding agent makes it possible to obtain a composition containing anthocyanin with good cosmetic properties, said composition being particularly non-greasy and non-sticky.
[0032] Furthermore, the present invention makes it possible to obtain compositions that remain transparent even after application to the skin.
[0033] The present invention also relates to a non-therapeutic cosmetic method for caring for and / or applying cosmetic treatments to keratin materials, the method comprising applying at least one cosmetic composition as defined above according to the invention to the surface of the keratin material.
[0034] The present invention also relates to a non-therapeutic cosmetic method for limiting skin darkening and / or improving the color and / or evenness of skin tone, the method comprising applying at least one cosmetic composition as previously defined to a surface of a keratin material.
[0035] The present invention also relates to a non-therapeutic cosmetic method for preventing and / or treating signs of aging of keratin materials, the method comprising applying at least one cosmetic composition as previously defined to the surface of the keratin material.
[0036] The present invention also relates to the use of at least one water-soluble UV masking agent for dissolving cyanide of formula (3) as defined below in an aqueous phase.
[0037] Other features, aspects and advantages of the invention will become apparent upon reading the following detailed description.
[0038] The compositions according to the invention are intended for topical application and therefore contain a physiologically acceptable medium. The term "physiologically acceptable medium" here means a medium compatible with keratin materials.
[0039] In the context of this invention, the term "keratin material" specifically refers to skin, scalp, keratin fibers (such as eyelashes, eyebrows, hair and body hair, nails), mucous membranes (such as lips), and more particularly skin and mucous membranes (body, face, periorbital area, eyelids, lips, preferably body, face and lips).
[0040] In the following text, unless otherwise specified, the limits of the range of values are included within that range, especially in expressions such as “between” and “ranging from… to…”.
[0041] Furthermore, the expressions “at least one” and “at least” used in this specification are equivalent to the expressions “one or more” and “greater than or equal to”, respectively.
[0042] According to the present invention, the terms "preventing" or "prevention" mean reducing the risk of a given phenomenon (i.e., signs of aging of keratin materials according to the present invention) or slowing down the occurrence of such a given phenomenon.
[0043] The term "organic UVA shielding agent" refers to any organic chemical molecule capable of absorbing UVA radiation in the wavelength range of at least 320 to 400 nm; said molecule may also absorb UVB radiation in the wavelength range of 280 to 320 nm.
[0044] The term "organic UVB shielding agent" should be understood to mean any organic chemical molecule that can only absorb UVB radiation in the wavelength range between 280 and 320 nm.
[0045] For the purposes of this invention, the term "transparent or translucent composition" refers to a composition having a turbidity value of less than 1000 NTU, preferably less than 800 NTU, even more preferably less than 500 NTU, even better less than 200 NTU, preferably less than 150 NTU, and especially less than 100 NTU. Preferably, the turbidity of the composition is at least equal to 1 NTU.
[0046] NTU (Naturometric Turbidity Unit) is a unit for measuring the turbidity of a composition. Turbidity measurements are performed, for example, using a Hach 2100P turbidimeter with tube index number AR397A cat 24347-06. Measurements are performed at ambient temperature (from 20°C to 25°C).
[0047] According to a specific embodiment of the invention, the composition is transparent and has a turbidity value between 1 and 200 NTU, preferably between 1 and 150 NTU, and preferably less than 100 NTU.
[0048] Preferably, the composition is transparent when applied to the skin, i.e., it does not leave a white residue after being applied to the skin. Detailed Implementation
[0049] merocyanine
[0050] According to the present invention, the family of cyanide corresponding to the following formula (3) and its geometric isomers, especially the E / E- or E / Z- geometric isomers, will be used:
[0051]
[0052] in:
[0053] A is -O- or -NH-;
[0054] R is C1-C 22 Alkyl, C2-C 22 alkenyl, C2-C 22 alkynyl group, C3-C 22 cycloalkyl or C3-C 22 Cycloalkenyl groups may have one or more O atoms inserted into them.
[0055] The anthocyanin compounds of the present invention can be in their E / E- or E / Z- geometrical isomers:
[0056]
[0057] Even more preferred compounds of formula (3) are those in which:
[0058] A is -O-; R is a C1-C that can be inserted with one or more Os. 22 alkyl.
[0059] In the compounds of formula (3), compounds selected from the following group and their geometric isomers, especially the E / E- or E / Z- geometric isomers, will be used more specifically:
[0060] [Table 1]
[0061]
[0062] [Table 1]
[0063]
[0064] [Table 1]
[0065]
[0066] According to a more particularly preferred embodiment of the invention, compound (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohexyl-2-en-1-yl}acetic acid 2-ethoxyethyl ester (25) will be used, in its E / E- and / or E / Z- geometry.
[0067] The E / Z form has the following structure:
[0068]
[0069] The E / E form has the following structure:
[0070]
[0071] According to the invention, the cyanine in the shielding portion is present in the composition in an amount of less than 3% by weight relative to the total weight of the composition, preferably less than or equal to 2.5% by weight, preferably between 0.01% by weight and 2.5% by weight, and even more preferably between 0.5% by weight and 1.5% by weight.
[0072] Compounds of formula (3) can be prepared according to the schemes described in patent application WO 2007 / 071582, IP.com publication (2009), 9(5A), 29-30IPCOM000182396D entitled “Process for producing 3-amino-2-cyclohexan-1-ylidene compounds” and US-A-4,749,643, column 13, line 66-column 14, line 57, and references cited herein.
[0073] Specifically, compounds of formula (3), such as compound (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohexyl-2-en-1-ylidene}acetic acid 2-ethoxyethyl ester (25), can be synthesized according to the synthetic scheme described in B. Winkler et al., Tetrahedron Letters, 55(2014) 1749-1751 entitled “A cyclic merocyanine UV-A absorber: mechanism of formation and crystal structure”, and are represented as follows for compounds of formula (3):
[0074] [Chemical Formula 3]
[0075]
[0076] And more specifically, for compound 25 described in Table 1:
[0077]
[0078] Water-soluble organic UV shielding agent
[0079] The compositions according to the present invention comprise at least one water-soluble organic UV shielding agent.
[0080] The term “water-soluble organic masking agent” should be understood to mean any organic masking agent that can be completely dissolved in an aqueous liquid phase in molecular form or in colloidal form (e.g., in micelle form).
[0081] Among the water-soluble organic UVA-masking agents that can be used according to the present invention, benzene-1,4-bis(3-methylene-10-camphor)sulfonic acid (INCI name: terephthalimethylene dicamphorsulfonic acid) and its various salts may be mentioned, particularly as described in patent applications FR-A-2528420 and FR-A-2639347. In particular, benzene-1,4-bis(3-methylene-10-camphorsulfonic acid) (INCI name: terephthalimethylene dicamphorsulfonic acid), such as that produced by Noval under the name Mexoryl® SX, may be mentioned.
[0082] These masking agents correspond to the following general formula (I):
[0083]
[0084] Where F represents a hydrogen atom, an alkali metal, or a group NH(R1)3 +The R1 group can be the same or different, representing a hydrogen atom, a C1 to C4 alkyl or hydroxyalkyl group, or a Mn group. + Mn + Mn represents a polyvalent metal cation, where n equals 2, 3, or 4. + Preferably, it represents the product selected from Ca. 2+ Zn 2+ Mg 2+ Ba 2+ Al 3+ and Zr 4+ Metal cations. It is clearly understood that compounds of formula (I) above can produce “cis-trans” isomers around one or more double bonds and all isomers fall within the context of this invention.
[0085] Among the water-soluble organic UVA masking agents that can be used according to the present invention, compounds containing at least two benzozolyl groups with sulfonic acid groups, such as those described in patent application EP-A-0669323, may also be mentioned.
[0086] These compounds are described and prepared according to the synthesis indicated in patent US 2 463 264 and patent application EP-A-0669323.
[0087] The compounds comprising at least two benzoxazole groups according to the present invention correspond to the following general formula (II):
[0088]
[0089] in,
[0090] - Z represents an organic residue with a valence of (l + n) containing one or more double bonds, the one or more double bonds being arranged such that the residue completes the double bonds of at least two benzoxazole groups defined in square brackets, so as to form a fully conjugated assembly structure.
[0091] - X' represents S, O, or NR 6 ;
[0092] - R 1 Represents hydrogen atoms, C1 to C 18 Alkyl, C1 to C4 alkoxy, C5 to C 15 Aryl, C2 to C 18 Acyloxy group or group SO3Y or COOY;
[0093] - Group R 2 R 3 R 4 and R 5 They can be the same or different, representing nitro groups or radicals R.1 ;
[0094] - R 6 Indicates a hydrogen atom, a C1 to C4 alkyl group, or a C1 to C4 hydroxyalkyl group;
[0095] - Y represents a hydrogen atom, Li, Na, K, NH4, 1 / 2Ca, 1 / 2Mg, 1 / 3Al, or a cation generated by neutralizing a free acid group with an organic nitrogen base;
[0096] - m is 0 or 1;
[0097] - n is a number from 2 to 6;
[0098] - l is a number from 1 to 4;
[0099] - This is on the premise that l + n does not exceed the value 6.
[0100] Among these compounds, 1,4-bis-benzimidazolyl-phenylene-3,3',5,5'-tetrasulfonic acid (INCI name: disodium phenyldibenzimidazolium tetrasulfonic acid) or its salts, having the following structure (III), are particularly marketed by Symrise under the name Neo Heliopan® AP:
[0101]
[0102] Preferably, the water-soluble shielding agent capable of absorbing UVA rays is benzene-1,4-bis(3-methylene-10-camphorsulfonic acid) (INCI name: terephthalimethylene dicamphorsulfonic acid), such as the product manufactured by Noval under the name Mexoryl SX.
[0103] The water-soluble organic UVB-masking agents that can be used according to the present invention are particularly selected from water-soluble cinnamic derivatives, such as ferulic acid or 3-methoxy-4-hydroxycinnamic acid; water-soluble benzyl camphor compounds; water-soluble phenylbenzimidazole compounds; water-soluble para-aminobenzoic acid (PABA) compounds; water-soluble salicylic acid compounds and mixtures thereof.
[0104] Examples of water-soluble organic UVB masking agents include phenylbenzimidazole compounds, such as 2-phenyl-1H-benzimidazole-5-sulfonic acid (INCI name: phenylbenzimidazole sulfonic acid), particularly those marketed by Merck under the trade name Eusolex 232. ® Sale.
[0105] The compositions according to the invention may further contain at least one mixed water-soluble shielding agent capable of absorbing UVA and UVB rays.
[0106] When the water-soluble UV masking agent is of the sulfonic acid type, it is preferably combined with an organic base such as an alkanolamine, or an inorganic base such as sodium hydroxide or potassium hydroxide.
[0107] The term "alkanolamine" refers to a C2-C structure containing at least one primary, secondary, or tertiary amine functional group and at least one alcohol, typically a primary alcohol functional group. 10 Compounds. Suitable alkanolamines include 2-amino-2-(hydroxymethyl)-1,3-propanediol (INCI name: tromethamine) and triethanolamine.
[0108] The water-soluble organic UV masking agent may be present in the composition at a concentration ranging from 0.1% to 19% by weight, and preferably from 0.5% to 12% by weight, and even more preferably from 3% to 10% by weight, relative to the total weight of the composition according to the invention.
[0109] Other UV shielding agents
[0110] The compositions according to the invention may contain at least one additional UV shielding agent in addition to the cyanine and water-soluble organic UV shielding agent of formula (3) as described above.
[0111] Other UV masking agents can be selected from lipophilic organic UV masking agents, water-dispersible organic UV masking agents, and inorganic UV masking agents.
[0112] According to specific embodiments, additional UV masking agents may be selected from water-dispersible organic UV masking agents and inorganic UV masking agents.
[0113] Lipophilic organic UV shielding agent
[0114] The term "organic lipophilic shielding agent" is intended to refer to any cosmetic or dermatological organic compound used to shield against UV radiation, which can be completely dissolved in the liquid fat phase in molecular form or in colloidal form (e.g., in micelles) in the liquid fat phase.
[0115] Lipophilic organic masking agents are particularly selected from cinnamic acid compounds, anthranilic acid ester compounds, salicylic acid compounds, benzoylmethane compounds, benzyl camphor compounds, benzophenone compounds, β,β-diphenyl acrylate compounds, triazine compounds, benzotriazole compounds, benzylmalonate compounds, especially those referenced in patent US 5,624,663, benzimidazole derivatives, imidazoline compounds, bis-benzoazole compounds as described in patents EP 669,323 and US 2,463,264, methylene bis(hydroxyphenylbenzotriazole) compounds as described in patent applications US 5,237,071, US 5,166,355, GB 2,303,549, DE 197,261,84 and EP 893,119, and benzoxazole compounds as described in patent applications EP 0,832,642, EP 1, EP 1 The masking polymers and masking silicones described in 300 137 and DE 101 62 844, especially those described in patent application WO 93 / 04665, α-alkylstyrene-based dimers such as those described in patent application DE 198 55 649, 4,4-diarylbutadiene compounds such as those described in patent applications EP0 967 200, DE 197 46 654, DE 197 55 649, EP-A-1 008 586, EP 1 133 980 and EP 133 981, and mixtures thereof.
[0116] Preferably, the lipophilic organic masking agent is selected from salicylic acid compounds, benzoylmethane compounds, benzyl camphor compounds, benzophenone compounds, triazine compounds, benzotriazole compounds, and mixtures thereof.
[0117] Examples of lipophilic organic photoprotectants include those referred to below by their INCI names and / or their chemical names.
[0118] Cinnamon acid Compounds:
[0119] Ethylhexyl methoxycinnamate, especially marketed by DSM Nutritional Products under the brand name Parsol® MCX,
[0120] Isoamyl p-methoxycinnamate, marketed by Symrise under the trade name Neo Heliopan E 1000®,
[0121] Benzoylmethane compounds:
[0122] Butylmethoxydibenzoylmethane, particularly marketed by DSM Nutrition Products under the trade name Parsol® 1789,
[0123] Salicylic acid compounds:
[0124] Homosalate, marketed by DSM Nutrition Products under the name Parsol® HMS,
[0125] Ethylhexyl salicylate, marketed by Symrise under the name Neo Heliopan® OS.
[0126] β,β-diphenylacrylate compounds:
[0127] Octyl cyanobenzyl acrylate, particularly marketed by BASF under the trade name Uvinul® N 539 T.
[0128] Benzophenone compounds:
[0129] Benzophenone-3 or hydroxybenzophenone, marketed by BASF under the trade name Uvinul® M 40.
[0130] Diethylaminohydroxybenzoylhexyl benzoate is marketed by BASF under the trade name Uvinul® A Plus, or as a mixture with ethylhexyl methoxycinnamate under the trade name Uvinul® A Plus B.
[0131] benzyl camphor compounds:
[0132] 4-Methylbenzyl camphor, marketed by Merck under the name Eusolex® 6300,
[0133] Phenylbenzotriazole compounds:
[0134] Cresoltrazol trisiloxane, manufactured by Noval under the name Mexoryl® XL.
[0135] Methylenebis(hydroxyphenylbenzotriazole) compounds:
[0136] Methylenebis-benzotriazolyltetramethylbutylphenol, especially in solid form, such as the product sold by Fairmount Chemical under the trade name MIXXIM BB / 100®.
[0137] Triazine compounds:
[0138] - 3,3'-(1,4-phenylene)bis(5,6-diphenyl-1,2,4-triazine), which has the INCI name phenylenebis-diphenyltriazine,
[0139] - Bis-ethylhexyloxyphenol methoxyphenyl triazine, marketed by DSM Nutritional Products under the trade name Parsol Shield® and by BASF under the trade name Tinosorb® S.
[0140] - Ethylhexyltriazine, particularly marketed by BASF under the trade name Uvinul® T 150,
[0141] - Diethylhexylbutamidotriazinone, marketed by 3V Sigma under the trade name Uvasorb® HEB.
[0142] - Symmetrical triazine masking agents substituted with naphthyl or polyphenyl groups, described in US 6,225,467, patent application WO 2004 / 085412 (see compounds 6 and 9) or the literature “Symmetrical triazine derivatives” (IP.COM) IPCOM000031257, Inc., West Henrietta, NY, US (September 20, 2004).
[0143] o-aminobenzoic acid compounds:
[0144] Menthyl anthranilate, marketed by Symrise under the trade name Neo Heliopan® MA,
[0145] benzyl malonate compounds:
[0146] Polysiloxanes containing benzyl malonate functional groups, such as polysiloxane-15 marketed by Hoffmann-La Roche under the trade name Parsol SLX®.
[0147] Water-dispersible organic UV shielding agents
[0148] The term "water-dispersible organic masking agent" refers to any organic masking agent capable of forming a homogeneous suspension of particles with a volume average size of less than 100 micrometers in an aqueous liquid phase. The volume average size is determined by laser diffraction particle size analysis.
[0149] Among water-dispersible organic masking agents, the following masking agents can be mentioned.
[0150] Benzophenone compounds:
[0151] 1,1'-(1,4-piperazinidyl)bis[1-[2-[4-(diethylamino)-2-hydroxybenzoyl]phenyl]methyl ketone] (CAS 919803-06-8), as described in application WO 2007 / 071584; this compound is advantageously used in a micronized form (volume average size of 0.02 to 2 µm) and particularly in an aqueous dispersion, which can be obtained, for example, by the micronization method described in applications GB-A-2 303 549 and EP-A-893 119.
[0152] Methylenebis(hydroxyphenylbenzotriazole) compounds:
[0153] Methylenebis(benzotriazolyl)tetramethylbutylphenol,
[0154] In at least one having structure C n H 2n+1 O(C6H 10 O5) x H alkyl polysaccharide surfactants (where n is an integer from 8 to 16 and x is a unit (C6H) 10 When the average degree of polymerization of O5 is in the range of 1.4 to 1.6, it is in the form of an aqueous dispersion of micronized particles having a volume average particle size in the range of 0.01 to 5 µm, more preferably 0.01 to 2 µm, and more particularly 0.020 to 2 µm, such as the aqueous dispersion described in patent GB-A-2 303 549, particularly the product sold by BASF under the trade name Tinosorb® M, or
[0155] At least one polyglycerol mono(C8-C) having a degree of polymerization of at least 5 glycerol 20 In the presence of alkyl esters, it exists as an aqueous dispersion of micronized particles having a volume average particle size ranging from 0.02 to 2 µm, more preferably from 0.01 to 1.5 µm, and more particularly from 0.02 to 1 µm, such as the aqueous dispersion described in application WO 2009 / 063392, particularly the product marketed by BASF under the name Tinosorb WPGL.
[0156] Triazine compounds:
[0157] - Bis-ethylhexyloxyphenol methoxyphenyl triazine, in its water-dispersible form, with the INCI name bis-ethylhexyloxyphenol methoxyphenyl triazine (and) acrylate / C12-22 alkyl methacrylate copolymer, is produced by BASF under the trade name Tinosorb® S LiteAqua.
[0158] - Symmetrical triazine masking agents substituted with naphthyl or polyphenyl groups, used in micronized form (average particle size 0.02 to 3 µm), which can be obtained, for example, by the micronization methods described in applications GB-A-2 303 549 and EP-A-893119, and particularly used in aqueous dispersion form, specifically marketed by BASF under the name Tinosorb® A2B and included in patent applications WO 06 / 035000, WO 06 / 034982, WO 06 / 034991, WO 06 / 035007, WO 2006 / 034992, and WO 2006 / 034985 as 2,4,6-tris(biphenyl)triazine and 2,4,6-tris(biphenyl)triazine.
[0159] Benzoxazole compounds:
[0160] 2-[4-(1,3-benzoxazole-2-yl)phenyl]-1,3-benzoxazole, with CAS number 904-39-2.
[0161] Inorganic UV shielding agent
[0162] The inorganic UV-masking agents that can be used according to the present invention are metal oxide pigments. More preferably, the inorganic UV-masking agents of the present invention are metal oxide particles with an average basic particle size of less than or equal to 0.5 µm, more preferably between 0.005 and 0.5 µm, even more preferably between 0.01 and 0.2 µm, even more preferably between 0.01 and 0.1 µm, and more particularly between 0.015 and 0.05 µm. They are specifically described in Annex VI of the updated EU Regulation No. 1223 / 2009 concerning cosmetic products, dated 22 September 2021, but are not limited to this list.
[0163] They may be selected, in particular, from titanium oxides, zinc oxides, iron oxides, zirconium oxides and cerium oxides, or mixtures thereof.
[0164] Such coated or uncoated metal oxide pigments are specifically described in patent application EP-A-0 518 773. Commercially available pigments that may be mentioned include products marketed by Croda, Tayca, and Merck.
[0165] Metal oxide pigments can be coated or uncoated.
[0166] The coated pigment is a pigment that has undergone one or more surface treatments with a compound that has chemical, electronic, mechanochemical, and / or mechanical properties, such as amino acids; beeswax; fatty acids; fatty alcohols; anionic surfactants; lecithin; sodium, potassium, zinc, iron, or aluminum salts of fatty acids; metal alkoxides (titanium or aluminum); polyethylene; silicone; proteins (collagen, elastin); alkanolamines; silicon dioxide; metal oxides; or sodium hexametaphosphate.
[0167] The coated pigments are more specifically titanium oxides, which have been coated with the following:
[0168] - Hydrated silica, such as MT-100WP from Imperial Chemical Industries,
[0169] - Silica and iron oxide, such as Sunveil F® from Ikeda Corporation,
[0170] - Silica and alumina, such as MT-500SA® and MT-100SA® from Imperial Chemical Industries and Tioveil™ AQ-N from Croda.
[0171] - Alumina, such as TTO-55 (A)® from Ishihara Corporation,
[0172] - Alumina and aluminum stearate, such as MT-100TV®, MT-100Z® and MT-01® from Imperial Chemical Industries, Solaveyil™ CT100 from Croda, and Eusolex T-AVO® from Merck.
[0173] - Silica, alumina, and alginate, such as MT-100AQ® from Teikoku Chemical Company.
[0174] - Alumina and aluminum lauryl,
[0175] - Iron oxide and ferric stearate,
[0176] - Zinc oxide and zinc stearate,
[0177] - Silica and alumina treated with silicone, such as MT-500SAS® or Microtitanium Dioxide MT-100SAS® from Imperial Chemical Industries.
[0178] - Silica, aluminum oxide, and aluminum stearate, and treated with silicone.
[0179] - Silicon dioxide and treated with silicone.
[0180] - Silicon dioxide treated with silicone, such as TTO-55(S)® from Ishihara Corporation.
[0181] - Triethanolamine
[0182] - Stearic acid, such as TTO-55 (C)® from Ishihara S.A.
[0183] - Sodium hexametaphosphate,
[0184] - TiO2 treated with octyltrimethylsilane
[0185] - TiO2 treated with polydimethylsiloxane
[0186] - Anatase / rutile TiO2 treated with polydimethylsiloxane
[0187] - By Croda Corporation under the trade name Solaveyil TM The CT-200 sold contains TiO2 coated with triisooctanoic acid glyceride, aluminum stearate, and aluminum oxide.
[0188] - By Croda Corporation under the trade name Solaveyil TM The CT-12W is sold as TiO2 coated with aluminum stearate, alumina, and silicone.
[0189] - TiO2 coated with lauroyl lysine
[0190] - Encapsulated with C9-C 15 TiO2 of fluorohydrophosphate and aluminum hydroxide.
[0191] It may also be mentioned that TiO2 pigments are doped with at least one transition metal (such as iron, zinc, or manganese, and more particularly manganese). Preferably, the doped pigment is in the form of an oily dispersion. The oil present in the oily dispersion is preferably selected from triglycerides, including those of capric / capric acid. The oily dispersion of the titanium oxide particles may also contain one or more dispersants, such as sorbitan esters, such as sorbitan isostearate, or polyoxyalkylene fatty acid esters of glycerol, such as Tri-PPG-3 myristyl ether citrate and polyglycerol-3 polyricinoleate. Preferably, the oily dispersion of the titanium oxide particles contains at least one dispersant selected from polyoxyalkylene fatty acid esters of glycerol. More specifically, an oily dispersion of manganese-doped TiO2 particles in decanoic acid / caprylic acid triglycerides can be mentioned in the presence of TRI-PPG-3 myristyl ether citrate, polyglycerol-3 polyricinoleate, and sorbitan isostearate, having the following INCI name: titanium dioxide (and) Tri-PPG-3 myristyl ether citrate (and) polyglycerol-3 polyricinoleate (and) sorbitan isostearate, or by Croda under the trade name Optisol. TM Products sold by OTP-1.
[0192] Uncoated titanium dioxide pigments are, for example, sold by Imperial Chemical Industries under the trade names MT-500B or MT-600B®, or by Evonik under the name Degussa P 25.
[0193] Uncoated zinc oxide pigments are, for example:
[0194] - Those sold by BASF under the name Z-Cote®;
[0195] - Those sold by Nanophase Technologies under the name NanoArc® Zinc Oxide.
[0196] The coated zinc oxide pigment is, for example:
[0197] - ZnO coated with polymethylhydrosiloxane;
[0198] - Solaveyil™ CZ-100 from Croda, dispersed in benzoic acid C 12 -C 15 Alkyl esters (INCI: zinc oxide (and) benzoic acid C12-15 alkyl esters (and) polyhydroxystearic acid (and) isostearic acid);
[0199] - Those sold by Daitopersion Zn-60VA® by Daitopersion Corporation (in C9-C with dispersant)12 (dispersions in alkanes);
[0200] - Those sold by Shin-Etsu under the name SPD-Z5® (ZnO coated with a silicone-grafted acrylic polymer dispersed in cyclodimethylsiloxane).
[0201] Uncoated cerium oxide pigments can be, for example, those sold by Solvay under the name Rhodigard® W185.
[0202] It may also be mentioned that metal oxides, especially mixtures of titanium dioxide and cerium dioxide, include equal weight mixtures of titanium dioxide and cerium dioxide coated with silica, and mixtures of titanium dioxide and zinc dioxide coated with alumina, silica and silicone or coated with alumina, silica and glycerol.
[0203] When the composition according to the invention contains an inorganic UV masking agent, coated or uncoated titanium dioxide pigments are particularly preferred.
[0204] According to specific embodiments, the total amount of additional UV-blocking agent present in the composition is less than or equal to 20% by weight, preferably less than or equal to 10% by weight, and even more preferably less than or equal to 5% by weight relative to the total weight of the composition.
[0205] According to a preferred embodiment, the total amount of additional UV masking agent present in the composition is between 0.1% by weight and 20% by weight, preferably between 0.5% by weight and 10% by weight, and even more preferably between 1% by weight and 5% by weight, relative to the total weight of the composition.
[0206] According to specific embodiments, the only UV masking agent present in the composition is a water-soluble organic masking agent and cyanine of formula (3).
[0207] For the purposes of this invention, the term "total amount of additional UV shielding agents" means the sum of the concentrations of the active substances of each UV shielding agent present in the composition, excluding the cyanine and water-soluble organic UV shielding agents of formula (3) as described above.
[0208] Aqueous phase
[0209] The composition according to the invention comprises at least one aqueous phase.
[0210] The aqueous phase contains water and optionally other water-soluble or water-miscible organic solvents.
[0211] The aqueous phase suitable for use in this invention may include, for example, water selected from natural springs, such as water from La Roche-Posay, water from Vittel, water from Saint-Gervais Mont-Blanc, or water from Vichy, or eau de toilette.
[0212] The aqueous phase may contain at least one other organic solvent that is soluble in water at 25°C, such as those selected from:
[0213] - C1-C4 monoalkanols. The term "C1-C4 monoalkanol" refers to any straight-chain or branched saturated alkane compound containing 1 to 4 carbon atoms and only one hydroxyl (OH) functional group. The C1-C4 monoalkanol present in the compositions of the present invention may be selected from methanol, ethanol, propanol, isopropanol, and butanol, or mixtures thereof. Ethanol will be selected more particularly;
[0214] - In particular, polyols having 2 to 20 carbon atoms, such as glycerol, diglycerol, propylene glycol, isopentyl glycol, dipropylene glycol, butanediol, hexanediol, octyl glycol, 1,3-propanediol, pentylene glycol, ethylene glycol or diethylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, sorbitol, simple sugars, water-soluble polyalkylene glycols; preferably polyols having 2 to 8 carbon atoms; and mixtures thereof.
[0215] According to one specific embodiment, the composition according to the invention comprises at least one C1-C4 monoalkanol, and more particularly ethanol.
[0216] Monoalkanols are typically present at a concentration ranging from 0.2% to 90% by weight, more preferably from 0.5% to 50% by weight, and most preferably from 1% to 15% by weight relative to the total weight of the composition.
[0217] According to another specific embodiment, the composition according to the invention comprises at least one polyol, particularly as described above. Preferably, it comprises at least 1% by weight of polyol relative to the total weight of the composition, preferably at least 5% by weight, preferably from 5% to 20% by weight, and preferably from 10% to 15% by weight of polyol relative to the total weight of the composition.
[0218] Preferably, the composition according to the invention comprises glycerol, butylene glycol, propylene glycol or dipropylene glycol, and mixtures thereof as polyols.
[0219] The compositions according to the invention are aqueous. For the purposes of this invention, the term "aqueous" refers to a composition in which the amount of fatty phase relative to the total weight of the composition is less than 10% by weight, preferably less than 5% by weight, and even more preferably less than 2% by weight. Advantageously, the compositions according to the invention are substantially aqueous, i.e., they contain no fatty phase.
[0220] According to a specific embodiment of the invention, the composition has a pH between 3 and 8. Advantageously, the pH of the composition is between 5 and 7.5.
[0221] According to specific embodiments, the cosmetic compositions according to the present invention may contain acidifiers and / or alkalizers.
[0222] Examples of acidifying agents that may be mentioned include mineral acids or organic acids, such as hydrochloric acid, phosphoric acid, sulfuric acid, carboxylic acids, such as acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acid.
[0223] Examples of alkalizing agents that may be mentioned include ammonia, alkali metal carbonates, alkanolamines (such as monoethanolamine, diethanolamine and triethanolamine) and their derivatives, sodium hydroxide or potassium hydroxide.
[0224] Preferably, the cosmetic composition comprises one or more alkalizing agents selected from alkanolamines, particularly triethanolamine, sodium hydroxide, and potassium hydroxide.
[0225] hydrophilic gelling agent
[0226] The compositions according to the present invention may contain at least one hydrophilic gelling agent (or hydrophilic thickener).
[0227] For the purposes of this invention, the term "hydrophilic gelling agent" (or "hydrophilic thickener") means a compound capable of gelling the aqueous phase of a composition according to the invention.
[0228] In particular, in the context of this patent application, the term "thickener" specifically means a reagent used to increase the viscosity of a mixture comprising 1% by weight of the reagent, 0.9% by weight of triethanolamine and water by at least 10 times, preferably at least 15 times, and preferably at least 20 times at a temperature of 25°C.
[0229] According to a specific embodiment of the present invention, the hydrophilic gelling agent is polymerized.
[0230] Hydrophilic gelling agents can be selected from anionic synthetic thickening polymers, nonionic thickening polysaccharides, sulfate-based thickening polysaccharides, and carboxylic acid branched thickening polysaccharides.
[0231] The term "carboxylic acid" refers to a substance containing at least one carboxylic acid functional group.
[0232] Preferably, the composition according to the invention is substantially free of (i.e., contains less than 0.4% by weight, preferably less than 0.3% by weight, preferably less than 0.2% by weight and even more preferably less than 0.1% by weight relative to the total weight of the composition), and preferably completely free of thickeners selected from clay, mica, modified starches such as phosphate starch and gellan gum.
[0233] Anionic synthetic thickening polymer
[0234] The compositions according to the present invention may contain anionic synthetic thickening polymers.
[0235] Preferably, the anionic synthetic thickening polymer is non-aromatic; this means that it does not contain any aromatic monomers.
[0236] Among the anionic synthetic thickening polymers that can be used, crosslinked homopolymers or copolymers of acrylic acid or methacrylic acid, either alone or as mixtures, crosslinked or non-crosslinked homopolymers of 2-acrylamido-2-methylpropanesulfonic acid or salts thereof, and copolymers of acrylamide-2-methylpropanesulfonic acid or salts thereof with one or more crosslinked or non-crosslinked nonionic monomers may be mentioned.
[0237] The first class of thickening polymers suitable for use are represented by cross-linked acrylic homopolymers. Among this type of homopolymer, those cross-linked with sugar-based allyl alcohol ethers can be mentioned, such as products sold by Lubrizol under the names Carbopol 980, 981, 954, 2984 and 5984, or by 3V under the names Synthalen M and Synthalen K.
[0238] These acrylic homopolymers can be present in the composition in particulate or non-particulate form. When they are in particulate form, their average size in the hydrated state is preferably less than or equal to 10 µm, and even more preferably less than or equal to 5 µm. Their average size in the dry or non-hydrated state is preferably less than or equal to 2 µm, and more preferably less than or equal to 1 µm.
[0239] Preferably, the acrylic homopolymer exists in a non-particulate form.
[0240] Preferably, a homopolymer of acrylic acid that is at least partially neutralized is used. The homopolymer used according to the invention is particularly selected from sodium polyacrylate and potassium polyacrylate. Sodium polyacrylate is preferred.
[0241] Examples of acrylic polymers that have been neutralized before use include:
[0242] - Sodium polyacrylate, such as those sold under the name Cosmedia SP® containing 90% solids and 10% water, or those sold under the name Cosmedia SPL® as a reverse emulsion containing about 60% dry active material, oil (hydrogenated polydecene) and surfactant (PPG-5 lauryl ether-5), are both sold by BASF.
[0243] - Partially neutralized sodium polyacrylate, particularly in the form of a reverse emulsion containing at least one polar oil, such as the product marketed by BASF under the name Luvigel® EM; and
[0244] - Its mixture.
[0245] Alternatively, an unneutralized acrylic polymer can be used, and then partially or completely neutralized before use by any suitable means, particularly by adding any base such as sodium hydroxide, potassium hydroxide, or an alkanolamine such as triethanolamine. This yields, in particular, sodium polyacrylate. Potassium polyacrylate is also suitable for use in this invention.
[0246] Suitable second-class thickening polymers are (meth)acrylic acid and acrylic acid C1-C. 30 Crosslinked copolymers of alkyl esters are representative examples.
[0247] Preferably, these copolymers are crosslinked copolymers of (meth)acrylic acid and C1-C6 alkyl acrylates.
[0248] The (meth)acrylic acid monomer is preferably present in an amount ranging from 20% to 80% by weight, more particularly from 25% to 70% by weight, and even more particularly from 35% to 60% by weight relative to the total weight of the copolymer.
[0249] The C1-C6 alkyl acrylate monomers are preferably present in an amount ranging from 15% to 80% by weight, more particularly from 25% to 75% by weight, and even more particularly from 40% to 65% by weight relative to the total weight of the copolymer. Among these monomers, methyl acrylate, ethyl acrylate, n-butyl acrylate, 2-hydroxyethyl acrylate, styrene, acrylamide, N,N-dimethylacrylamide, tert-butylacrylamide, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, and 2-hydroxyethyl methacrylate may be mentioned.
[0250] Such copolymers are typically partially or completely crosslinked with at least one conventional crosslinking agent. Crosslinking agents are, in particular, polyunsaturated compounds. These compounds are especially polyolefin ethers of sucrose or polyols, diallyl phthalate, divinylbenzene, allyl (meth)acrylate, ethylene glycol di(meth)acrylate, methylenebisacrylamide, trimethylolpropane tri(meth)acrylate, diallyl itaconic acid, diallyl fumarate, diallyl maleate, zinc (meth)acrylate, and castor oil or polyol derivatives made from unsaturated carboxylic acids. As crosslinking agents, unsaturated monomeric compounds comprising reactive groups capable of reacting with unsaturated substances to form crosslinked copolymers may also be used. The content of the crosslinking agent relative to the total weight of the copolymer typically ranges from 0.01% to 5% by weight, preferably from 0.03% to 3% by weight, and even more particularly from 0.05% to 1% by weight.
[0251] The preferred crosslinked copolymers of (meth)acrylic acid and C1-C6 alkyl acrylates according to the present invention are selected from crosslinked copolymers of methacrylic acid and C1-C6 alkyl acrylates, crosslinked copolymers of acrylic acid and C1-C6 alkyl acrylates, and more particularly crosslinked copolymers of methacrylic acid and ethyl acrylate.
[0252] According to a particularly preferred form, the copolymers of the present invention can be, in particular, in the form of a dispersion in water. The number-average size of the copolymer particles in the dispersion is generally between 10 and 500 nm, preferably between 20 and 200 nm, and more preferably between 50 and 150 nm.
[0253] Among the crosslinked copolymers of (meth)acrylic acid and C1-C6 alkyl acrylates, the following products may be mentioned: Coatex, under the name Viscoatex 538C, is a crosslinked copolymer of (meth)acrylic acid and C1-C4 ethyl acrylate, presented as an aqueous dispersion containing 38% active ingredient; or Röhm & Haas, under the name Aculyn 33, is a crosslinked copolymer of acrylic acid and ethyl acrylate, presented as an aqueous dispersion containing 28% active ingredient. More specifically, Lubrizol, under the name Carbopol Aqua SF-1, manufactures and markets a crosslinked methacrylic acid / ethyl acrylate copolymer in the form of a 30% aqueous dispersion.
[0254] The third class of suitable thickening polymers is represented by cross-linked or non-cross-linked 2-acrylamido-2-methylpropanesulfonic acid (AMPS®) homopolymers or their salts. These homopolymers can be cross-linked or non-cross-linked.
[0255] Such homopolymers can have a number-average molecular weight ranging from 1,000 to 20,000,000 g / mol, preferably from 20,000 to 5,000,000, and even more preferably from 100,000 to 1,500,000 g / mol.
[0256] More specifically, 2-acrylamido-2-methylpropanesulfonic acid is used, as well as its partially or completely neutralized form.
[0257] When the polymer is crosslinked, the crosslinking agent can be selected from polyene unsaturated compounds commonly used for crosslinking polymers obtained by free radical polymerization. Examples of crosslinking agents that may be mentioned include divinylbenzene, diallyl ether, dipropylene glycol diallyl ether, polyethylene glycol diallyl ether, triethylene glycol divinyl ether, hydroquinone diallyl ether, ethylene glycol or tetraethylene glycol di(meth)acrylate, trimethylolpropane triacrylate, methylenebisacrylamide, methylenebismethylacrylamide, triallylamine, triallyl cyanurate, diallyl maleate, tetraallyl ethylenediamine, tetraallylpropoxyethane, trimethylolpropane diallyl ether, allyl (meth)acrylate, allyl ethers of sugar series alcohols, or other allyl ethers or vinyl ethers of polyfunctional alcohols, as well as allyl esters of phosphoric acid and / or vinylphosphonic acid derivatives, or mixtures of these compounds.
[0258] According to a preferred embodiment of the invention, the crosslinking agent is selected from methylenebisacrylamide, allyl methacrylate, and trimethylolpropane triacrylate (TMPTA). The degree of crosslinking typically ranges from 0.01 mol% to 10 mol% relative to the polymer, and more particularly from 0.2 mol% to 2 mol%.
[0259] Homopolymers contain only monomers with sulfonic acid groups, and if they are crosslinked, they contain one or more crosslinking agents.
[0260] Preferred 2-acrylamido-2-methylpropanesulfonic acid homopolymers are typically characterized by containing randomly distributed units of the following:
[0261] a) Units of the following general formula (1) ranging from 90% by weight to 99.9% by weight:
[0262]
[0263] Where X + Cation X represents a proton, alkali metal cation, alkaline earth metal cation, or ammonium ion, not exceeding 10 mol% of the total cation. + It could be proton H + ;
[0264] b) From 0.01% by weight to 10% by weight of crosslinking units derived from at least one monomer containing at least two olefinic double bonds; the weight percentage is defined relative to the total weight of the polymer.
[0265] The more particularly preferred homopolymer according to the invention comprises from 98% to 99.5% by weight of units of formula (1) and from 0.2% to 2% by weight of crosslinking units.
[0266] One type of polymer that can be mentioned in particular is the crosslinked and neutralized 2-acrylamido-2-methylpropanesulfonic acid homopolymer sold by Clariant under the trade name Hostacerin AMPS® (CTFA name: ammonium polyacrylamide dimethyl taurate).
[0267] The polymer can also be an amphiphilic homopolymer (or a hydrophobically modified homopolymer), selected from those obtained by reacting with C6-C. 22 Reactively modified random amphiphilic 2-acrylamido-2-methylpropanesulfonic acid polymers of n-monoalkylamines or di-n-alkylamines, such as those described in WO-A-00 / 31154, are grafted homopolymers.
[0268] The fourth class of suitable thickening polymers is represented by copolymers of acrylamide-2-methylpropanesulfonic acid or its salts with one or more nonionic monomers. They can be cross-linked or non-cross-linked.
[0269] When the polymer is crosslinked, the crosslinking agent can be selected from polyene unsaturated compounds commonly used for crosslinking polymers obtained through free radical polymerization. Such crosslinking agents are described above.
[0270] According to a preferred embodiment of the invention, the crosslinking agent is selected from methylenebisacrylamide, allyl methacrylate, and trimethylolpropane triacrylate (TMPTA). The degree of crosslinking typically ranges from 0.01 mol% to 10 mol% relative to the polymer, and more particularly from 0.2 mol% to 2 mol%.
[0271] The copolymers according to the invention are obtained from AMPS® and one or more hydrophilic or hydrophobic olefinically unsaturated nonionic monomers, and if they are crosslinked, one or more crosslinking agents (as defined above).
[0272] The 2-acrylamido-2-methylpropanesulfonic acid monomer of the copolymer contained in the composition according to the invention is in free form or is partially or completely neutralized by: inorganic bases (sodium hydroxide, potassium hydroxide or ammonia) or organic bases (such as mono-, di- or triethanolamine, aminomethylpropanediol, N-methylglucosamine), basic amino acids (such as arginine and lysine), and mixtures thereof.
[0273] Preferably, the 2-acrylamido-2-methylpropanesulfonic acid monomer is partially or completely salted in the form of an ammonium salt or a sodium salt.
[0274] Preferably, the 2-acrylamido-2-methylpropanesulfonic acid monomer is fully salted, preferably in the form of an ammonium salt or a sodium salt.
[0275] AMPS® copolymers contain one or more nonionic monomers selected from water-soluble olefinically unsaturated monomers, hydrophobic monomers, or mixtures thereof.
[0276] Examples of nonionic water-soluble monomers that can be mentioned include:
[0277] -(methyl)acrylamide,
[0278] - N-vinylacetamide and N-methyl-N-vinylacetamide,
[0279] - N-vinylformamide and N-methyl-N-vinylformamide,
[0280] - Maleic anhydride
[0281] - Ethyleneamine,
[0282] - Including N-vinyl lactams containing cycloalkyl groups with 4 to 9 carbon atoms, such as N-vinylpyrrolidone, N-butyrolactam, and N-vinylcaprolactam.
[0283] - Vinyl alcohols with the formula CH2=CHOH
[0284] - The water-soluble vinyl monomer of formula (2):
[0285]
[0286] in:
[0287] - R 15 Selected from H, -CH3, -C2H5 and -C3H7,
[0288] - X2 is selected from -OR 16 Type of alkyl oxide, wherein R 16 It is a straight-chain or branched, saturated or unsaturated hydrocarbon-based group containing 1 to 6 carbon atoms, which may optionally be replaced by: halogen atoms (iodine, bromine, chlorine or fluorine); hydroxyl (-OH) groups; ethers.
[0289] For example, references are made to glycidyl (meth)acrylate, hydroxyethyl (meth)acrylate, and (meth)acrylates of ethylene glycol, diethylene glycol, or polyalkylene glycol.
[0290] Preferably, the water-soluble monomer is selected from acrylamide, vinylpyrrolidone, and hydroxyalkyl (meth)acrylate, more particularly vinylpyrrolidone.
[0291] Examples of copolymers of AMPS® and hydrophilic monomers according to the present invention include:
[0292] - Copolymers of acrylamide-2-methylpropanesulfonic acid and vinylpyrrolidone, especially commercial products such as Aristoflex AVC sold by Clariant.
[0293] - Crosslinked acrylamide / acrylamido-2-methylpropanesulfonate copolymer, such as that used in the commercial product Sepigel 305® (INCI name: polyacrylamide / C 13 -C 14 The copolymer in isoparaffin / lauryl ether-7 or the copolymer used in a commercial product sold by Seppic Company under the name Simulgel 600® (INCI name: acrylamide / sodium acryloyl dimethyl taurate / isohexadecane / polysorbate-80);
[0294] - Copolymers of AMPS® and hydroxyethyl acrylate, such as sodium AMPS® / hydroxyethyl acrylate copolymers, as used in commercial products sold by Seppic under the name Simulgel NS® (INCI name: hydroxyethyl acrylate / sodium acryloyl dimethyl taurate copolymer (and) squalane (and) polysorbate 60);
[0295] - Hydrophobically modified AMPS® copolymers, such as those known under the INCI name: Acryloyldimethyltaurate ammonium / stearyl alcohol polyether-25 methacrylate crosspolymer, are marketed by Clariant under the trade name Aristoflex HMS.
[0296] The concentration of the anionic synthetic thickening polymer (i.e., the active substance) relative to the total weight of the composition is typically from 0.05 wt% to 35 wt%, preferably from 0.1 wt% to 20 wt%, preferably from 0.2 wt% to 10 wt%, preferably from 0.25 wt% to 5 wt%, and even more particularly from 0.3 wt% to 3 wt%.
[0297] Thickening polysaccharides
[0298] The compositions according to the present invention may further comprise a thickening polymer selected from nonionic thickening polysaccharides, sulfated thickening polysaccharides, and carboxylic acid branched thickening polysaccharides.
[0299] Among nonionic thickening polysaccharides, nonionic cellulose-based thickening polysaccharides are particularly noteworthy.
[0300] Preferably, the cellulose used in the composition according to the invention is selected from cellulose that does not contain hydrophobic chains and nonionic cellulose that includes one or more hydrophobic chains.
[0301] Preferably, the cellulose used according to the invention is a cellulose ether. Even more preferably, these celluloses are nonionic hydroxyalkyl celluloses, and particularly hydroxyethyl cellulose or hydroxypropyl cellulose. They may or may not contain fatty chains. Among nonionic celluloses that do not contain fatty chains, hydroxyethyl cellulose, hydroxypropyl cellulose, and hydroxypropyl methyl cellulose may be mentioned. A particularly suitable hydroxyethyl cellulose is Cellosize HEC QP-4400 H (INCI name: hydroxyethyl cellulose), sold by Amerchol.
[0302] Cellulose modified with groups comprising one or more nonionic fatty chains, which can be used according to the present invention, is particularly:
[0303] - Nonionic hydroxyethyl cellulose modified with groups comprising at least one fatty chain, such as alkyl, aralkyl, or alkylaryl groups, or mixtures thereof, wherein the alkyl group is preferably C8-C. 22 Groups, such as those found in Natrosol Plus Grade 330 CS® (C) sold by Ashland. 16 Alkyl), corresponding to the INCI name cetyl hydroxyethyl cellulose, or Bermocoll EHM 100® sold by AkzoNobel.
[0304] - Those modified with alkylphenyl polyalkylene glycol ether groups, such as Amercell Polymer HM-1500® (nonylphenyl polyethylene glycol (15) ether) sold by Amercell Corporation, correspond to the INCI name nonoxynyl hydroxyethyl cellulose.
[0305] Among sulfated ester-based thickening polysaccharides, sulfated ester-based polysaccharides that do not contain rhamnose are particularly noteworthy. These sulfated ester-based polysaccharides are preferably carrageenan.
[0306] Carrageenan is a polysaccharide that constitutes the cell walls of various red algae belonging to the families Gigartinacae, Hypneaceae, Furcellariaceae, and Polyideaceae (Rhodophyceae). They consist of long galactan chains and anionic polyelectrolytes. Their molecular weight can be greater than 10. 6These linear polymers formed from disaccharide units consist of two D-galactopyranose units linked alternately by α- and β-bonds. They are highly sulfated polysaccharides (20%–50%) and the α-D-galactopyranose residues can be in a 3',6'-dehydrated form.
[0307] Initially, carrageenan was subdivided into two series based on its solubility in potassium chloride (KCl). The KCl-soluble portion was indicated by the prefix "κ," while the term "λ" was reserved for the insoluble portion. Later, the classification was based on the number and position of the sulfate ester groups, as well as the presence of a 3',6'-dehydration bridge on the β-D-galactopyranoside residue. This resulted in four main series: κ, λ, β, and ω.
[0308] Different types of carrageenan do not exist in pure forms, but rather in heterozygous forms. Therefore, in their natural state, κ- and... Carrageenan exists in a κ-ι hybrid form, but one of the two structures may be more dominant than the other. The κ- structure... The heterozygous state can be elucidated using specific enzymes that allow for the enrichment or reduction of one of the two forms. Carrageenan can coexist with its precursors. Different sources of carrageenan can coexist in a heterozygous structure.
[0309] Preferably, the composition according to the invention comprises one or more carrageenan-type sulfated polysaccharides. The carrageenan-type sulfated polysaccharides may or may not be chemically modified. Preferably, the carrageenan-type sulfated polysaccharides are not chemically modified. Preferably, the molecular weight (MW) of the polysaccharide is between 100,000 and 1,000,000, and more preferably between 250,000 and 800,000. Examples of carrageenan-type sulfated polysaccharides include Satiagum UTC 10 or Satiagum VPC 410 from Cargill and Welgeenan ED 1039 from Eurogum.
[0310] Among carboxylic acid branched thickening polysaccharides, anionic branched polysaccharides based on glucose, mannose, acetylated mannose, pyruvate, and glucuronic acid are particularly noteworthy. Xanthan gum is a preferred example of such a polysaccharide.
[0311] Xanthan gum is a heteropolysaccharide produced industrially by aerobic fermentation of the bacterium *Xanthomonas campestris*. Similar to cellulose, its structure consists of a backbone of β(1,4)-linked β-D-glucose. One of the glucose molecules carries a trisaccharide side chain consisting of α-D-mannose, β-D-glucuronic acid, and terminal β-D-mannose. The internal mannose residues are typically acetylated at carbon 6. Approximately 30% of the terminal mannose residues carry pyruvate groups chelated between carbons 4 and 6. The charged pyruvate and glucuronic acid are ionizable, thus contributing to the anionic nature of xanthan gum (negative charge reduced to pH 1). The content of pyruvate and acetate residues varies depending on the bacterial strain, fermentation method, post-fermentation conditions, and purification steps. These groups can be commercially available using Na... + K + or Ca 2+ Ion neutralization (Satia, 1986). The neutralized form can be converted back to the acidic form through ion exchange or by dialysis of an acidic solution.
[0312] For an aqueous composition containing 1% xanthan gum, the xanthan gum has a molecular weight between 1,000,000 and 50,000,000 and a viscosity between 0.6 and 1.65 Pa·s (measured at 60 rpm on an LVT-type Brookfield viscometer at 25°C).
[0313] Xanthan gum is represented by products such as Rhodicare® sold by PMC Ouvrie, Satiaxane™ sold by Cargill Texturizing Solutions (for use in the food, cosmetics and pharmaceutical industries), Novaxan™ sold by ADM, and Kelzan® and Keltrol® sold by CP-Kelco.
[0314] The concentration of the thickening polysaccharide used in the composition according to the invention is in the range of 0.01% to 20% by weight, preferably 0.02% to 10% by weight, preferably 0.03% to 8% by weight, preferably 0.05% to 5% by weight, and even more preferably 0.1% to 3% by weight relative to the total weight of the composition.
[0315] According to a preferred embodiment, the composition according to the invention comprises a thickener selected from crosslinked acrylic homopolymers, crosslinked copolymers of (meth)acrylic acid and C1-C6 alkyl acrylates, copolymers of acrylamide-2-methylpropanesulfonic acid with one or more nonionic monomers, crosslinked and preferably neutralized 2-acrylamido-2-methylpropanesulfonic acid homopolymers, hydroxyethyl cellulose, carrageenan, and xanthan gum.
[0316] According to a preferred embodiment, the composition according to the invention comprises a thickener selected from cross-linked acrylic homopolymers, cross-linked and preferably neutralized 2-acrylamido-2-methylpropanesulfonic acid homopolymers, hydroxyethyl cellulose, carrageenan, and xanthan gum.
[0317] The compositions according to the invention may also comprise a mixture of several thickening polymers, typically a mixture of at least two or more thickening polymers. The compositions may typically comprise at least one anionic synthetic thickening polymer and at least one thickener selected from nonionic thickening polysaccharides, sulfated thickening polysaccharides, carboxylic acid branched thickening polysaccharides, and mixtures thereof.
[0318] According to specific embodiments of the present invention, the total concentration range of the thickener used in the composition is from 0.01 wt% to 50 wt%, preferably from 0.1 wt% to 20 wt%, preferably from 0.2 wt% to 10 wt%, preferably from 0.3 wt% to 8 wt%, and even more preferably from 0.5 wt% to 3 wt% relative to the total weight of the composition.
[0319] additive
[0320] The compositions according to the invention may also contain conventional cosmetic adjuvants particularly selected from the following: emollients, humectants, sunscreens, stabilizers, skin moisturizers, silicones, defoamers, fragrances, preservatives, anionic, cationic, nonionic, amphoteric or amphoteric surfactants, surfactants, fillers, polymers, propellants, or any other ingredients commonly used in the cosmetic and / or dermatological fields.
[0321] Among active agents used in the care of keratin materials (such as skin, lips, scalp, hair, eyelashes, or nails) may be mentioned, for example: vitamins and their derivatives or precursors, alone or in mixtures; antioxidants; free radical scavengers; anti-pollution agents; self-tanning agents; anti-glycation agents; sedatives; deodorants; essential oils; NO-synthesizers; agents for stimulating the synthesis of macromolecules in the dermis or epidermis and / or for preventing their degradation; agents for stimulating fibroblast proliferation; agents for stimulating keratinocyte proliferation; muscle relaxants; fresheners; tightening agents; matting agents; bleaching agents; pigmentation promoters; keratolytic agents; desquamating agents; moisturizers; anti-inflammatory agents; antimicrobial agents; slimming agents; agents acting on cellular energy metabolism; insect repellents; substance P antagonists or CRGP antagonists; agents for preventing hair loss; anti-wrinkle agents; anti-aging agents.
[0322] Those skilled in the art will select the active agent based on the desired effect on the skin, hair, eyelashes, eyebrows, and nails.
[0323] Of course, those skilled in the art will carefully select one or more of the above-mentioned optional additional compounds and / or their amounts so that the advantageous properties inherent to the composition according to the invention are not or substantially not adversely affected by the contemplated one or more additives.
[0324] Presentation format
[0325] The compositions according to the invention are aqueous, meaning they contain at least one aqueous phase.
[0326] The compositions according to the invention are in a purely aqueous form, that is, these compositions contain a fatty phase in an amount of less than 10% by weight, preferably less than 5% by weight, and even more preferably less than 1% by weight relative to the total weight of the composition. Advantageously, the compositions according to the invention are substantially aqueous, i.e., they do not contain any fatty phase.
[0327] The compositions according to the invention can be in the form of an aqueous solution or a hydrogel. According to a preferred embodiment, the composition is in the form of a hydrogel.
[0328] The compositions according to the invention can be applied to many treatments, especially for cosmetic treatments of skin, lips and hair (including scalp), particularly for protecting and / or caring for skin, lips and / or hair and / or for applying makeup to skin and / or lips.
[0329] Another subject of the invention comprises the use of compositions according to the invention as defined above for the manufacture of products for cosmetic treatment of skin, lips, nails, hair, eyelashes, eyebrows and / or scalp, particularly care products, sunscreen products and cosmetic products.
[0330] Another subject of the invention comprises a non-therapeutic cosmetic method for caring for and / or applying cosmetic treatments to keratin materials, the method comprising applying at least one composition as defined above according to the invention to the surface of the keratin material.
[0331] Another subject of the present invention consists of the use of at least one hydrophilic organic UV masking agent to dissolve cyanine as defined above in formula (3).
[0332] According to the present invention, one or more water-soluble organic UV masking agents make it possible to dissolve the cyanide according to the present invention in an aqueous phase. Example
[0333] The invention will now be described in more detail by way of examples, which do not in any way limit the scope of the invention. However, these examples enable the display of specific features, variations, and preferred embodiments of the invention.
[0334] A / Example of synthesis of a merocyanine of formula (3)
[0335] Example A1: Preparation of compound (14)
[0336]
[0337] 122.23 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one was alkylated with dimethyl sulfate or alternatively with diethyl sulfate in the presence of a base and optionally a solvent, and then treated with approximately 75.45 g of ethyl cyanoacetate in an equimolar proportion.
[0338] Use the base / solvent combinations shown in the table below.
[0339] [Table 2]
[0340]
[0341] The completion of the alkylation reaction can be monitored, for example, by methods such as TLC, GC or HPLC.
[0342] 162.30 g of the compound was obtained as a brown oily substance (14).
[0343] After crystallization, a product in the form of pale yellow crystals is obtained.
[0344] Melting point: 92.7°C.
[0345] Example A2: Preparation of compound (15)
[0346]
[0347] 101.00 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one was alkylated with dimethyl sulfate or alternatively with diethyl sulfate in the presence of a base and optionally a solvent, and then treated with approximately equimolar amounts of 86.00 g of 2-cyano-N-(3-methoxypropyl)acetamide.
[0348] Use the base / solvent combinations shown in the table below.
[0349] [Table 3]
[0350]
[0351] A crude product in the form of a dark brown oil was obtained (15).
[0352] Following silica gel column chromatography (elution buffer: 99 / 1 toluene / methanol), 81.8 g of the product in the form of pale yellow crystals was obtained.
[0353] Melting point: 84.7°C-85.3°C.
[0354] Example A3: Preparation of compound (27)
[0355]
[0356] 13.09 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one was alkylated with dimethyl sulfate or alternatively with diethyl sulfate in the presence of a base and optionally a solvent, and then treated with 10.12 g of isobutyl cyanoacetate.
[0357] Use the base / solvent combinations shown in the table below.
[0358] [Table 4]
[0359]
[0360] 15.97 g of crude product in the form of a dark brown oil was obtained (27).
[0361] Following silica gel column chromatography (elution: toluene / acetone), 13.46 g of the product in the form of pale yellow crystals was obtained.
[0362] Melting point: 96.3°C.
[0363] Example A4: Preparation of compound (25)
[0364]
[0365] 148.4 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one was alkylated with dimethyl sulfate or alternatively with diethyl sulfate in the presence of an organic base and solvent, and then treated with 130.00 g of 2-ethoxyethyl cyanoacetate.
[0366] Use the base / solvent combinations shown in the table below.
[0367] [Table 5]
[0368]
[0369] B / Formulation examples
[0370] In these examples, the amount of the component present in the composition is given as a percentage of the weight of the active substance relative to the total weight of the composition.
[0371] Scheme for assessing solubility
[0372] The solubility of cyanine in aqueous solutions can be assessed macroscopically and / or microscopically. Cyanine is considered soluble if the solution appears clear and translucent to the eye at ambient temperature and does not exhibit any visible crystals under white light or polarized light microscopy (objectives ×20 to ×40).
[0373] In the following example, solubility will be assessed macroscopically. The assessment will be conducted at ambient temperature after 24 hours. During this period, the solution will be stored at ambient temperature.
[0374] Example 1 : solubilization in the presence of 2-phenyl-1 H-benzimidazole-5-sulfonic acid or a salt thereof
[0375] Prepare the following solutions using the following methods.
[0376] [Table 6]
[0377]
[0378] The various ingredients were mixed in a beaker, and the mixture was stirred at ambient temperature for 2 hours using a magnetic stirrer. The resulting formulation was then stored at ambient temperature for 24 hours, and the anthocyanin solubility was then macroscopically evaluated.
[0379] These results indicate that water-insoluble compound 25 dissolves in the presence of 2-phenyl-1H-benzimidazole-5-sulfonic acid and / or its salts.
[0380] Example 2: solubilization in the presence of benzene-1,4-di(3-methylene-10- camphor sulfonic acid) and / or a salt thereof
[0381] Prepare the following solutions using the following methods.
[0382] [Table 7]
[0383]
[0384] The various ingredients were mixed in a beaker, and the mixture was stirred at ambient temperature for 2 hours using a magnetic stirrer. The resulting formulation was then stored at ambient temperature for 24 hours, and the anthocyanin solubility was then macroscopically evaluated.
[0385] These results indicate that water-insoluble compound 25 is soluble in the presence of benzene-1,4-bis(3-methylene-10-camphorsulfonic acid) and / or its salts.
[0386] Example 3: solubilization in the presence of 1,4-bis-benzimidazolyl- phenylene-3,3',5,5'-tetrasulfonic acid and / or a salt thereof solubilization
[0387] Prepare the following solutions using the following methods.
[0388] [Table 8]
[0389]
[0390] The various ingredients were mixed in a beaker, and the mixture was stirred at ambient temperature for 2 hours using a magnetic stirrer. The resulting formulation was then stored at ambient temperature for 24 hours, and the anthocyanin solubility was then macroscopically evaluated.
[0391] These results indicate that water-insoluble compound 25 is soluble in the presence of 1,4-bis-benzimidazolylphenylene-3,3',5,5'-tetrasulfonic acid and / or its salts.
[0392] Example 4: Transparent water-based slurry
[0393] Prepare the following composition.
[0394] [Table 9]
[0395]
[0396] Preparation mode
[0397] Phase A1 was prepared at 50°C with magnetic stirring, and phase A2 was prepared at ambient temperature with magnetic stirring. Phase A2 was then slowly added to phase A1 with stirring until a clear mixture was obtained. The mixture was then returned to ambient temperature, and phase B was then added with stirring.
Claims
1. A water-based cosmetic or dermatological composition, said composition comprising: a) At least one cyanide corresponding to the following formula (3), and its geometric isomers, especially the E / E- or E / Z- geometric isomers: in: A is -O- or -NH-; R is C1-C 22 Alkyl, C2-C 22 alkenyl, C2-C 22 alkynyl group, C3-C 22 cycloalkyl or C3-C 22 Cycloalkenyl, wherein the group may be inserted with one or more O atoms; Its amount is less than 3% by weight relative to the total weight of the composition; and b) At least one water-soluble organic UV shielding agent.
2. The composition according to claim 1, wherein the compound of formula (3) is one in which A is -O-; R is a Cl-C compound that may be inserted with one or more O atoms. 22 alkyl.
3. The composition according to any one of claims 1 and 2, wherein, The cyanine in formula (3) is selected from the following compounds and their E / E- or E / Z- geometric isomers: [Table 1] 。 4. The composition according to any one of claims 1 to 3, wherein the cyanine of formula (3) is (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohexyl-2-en-1-yl}acetic acid 2-ethoxyethyl ester (25), having its E / Z geometry and having the following structure: and / or having its E / E geometry, having the following structure: 。 5. The composition according to any one of claims 1 to 4, wherein the amount of the cyanine corresponding to the following formula (3) and its geometric isomer form, especially its E / E- or E / Z- geometric isomer form, is less than or equal to 2.5% by weight of the total weight of the composition, preferably between 0.01% by weight and 2.5% by weight, and even more preferably between 0.5% by weight and 1.5% by weight.
6. The composition according to any one of claims 1 to 5, wherein the water-soluble organic UV shielding agent is selected from benzene-2-phenyl-1H-benzimidazole-5-sulfonic acid (INCI name: phenylbenzimidazole sulfonic acid); benzene-1,4-bis(3-methylene-10-camphor sulfonic acid) (INCI name: terephthalimethylene dicamphor sulfonic acid); 1,4-bis-benzimidazole-phenylene-3,3',5,5'-tetrasulfonic acid (INCI name: disodium phenyldibenzimidazole tetrasulfonate); and salts thereof.
7. The composition according to any one of claims 1 to 6, wherein the water-soluble organic UV masking agent is present at a concentration ranging from 0.1% to 19% by weight relative to the total weight of the composition, and preferably from 0.5% to 12% by weight, and even more preferably from 3% to 10% by weight.
8. The composition according to any one of claims 1 to 7, wherein the composition comprises at least one additional UV masking agent selected from lipophilic organic UV masking agents, water-dispersible organic UV masking agents, and inorganic UV masking agents, preferably selected from water-dispersible organic UV masking agents and inorganic UV masking agents.
9. The composition according to claim 8, wherein the lipophilic organic UV masking agent is selected from cinnamic acid compounds; anthranilate compounds, salicylic acid compounds, benzoylmethane compounds, benzyl camphor compounds, benzophenone compounds, β,β-diphenyl acrylate compounds; triazine compounds, benzotriazole compounds, benzylmalonate compounds, benzimidazole derivatives, imidazoline compounds, bis-benzoazole compounds; methylene bis(hydroxyphenylbenzotriazole) compounds; benzoxazole compounds, masking polymers and masking silicones, dimers derived from α-alkylstyrene; 4,4-diarylbutadiene compounds; and mixtures thereof; preferably salicylic acid compounds, benzoylmethane compounds, benzyl camphor compounds, benzophenone compounds, triazine compounds, benzotriazole compounds, and mixtures thereof.
10. The composition according to any one of claims 8 and 9, wherein, The water-dispersible organic UV shielding agent is selected from at least one having a structure C. n H 2n+1 O(C6H 10 O5) x In the case of H-alkyl polysaccharide surfactants, where n is an integer from 8 to 16 and x is a unit (C6H) 10 The average degree of polymerization of O5 is 1.4 to 1.6, and the product is a methylenebis-benzotriazolyltetramethylbutylphenol in the form of an aqueous dispersion of micronized particles having an average particle size of 0.01 to 5 µm, more preferably 0.01 to 2 µm, and more particularly 0.020 to 2 µm; in at least one polyglycerol mono(C8-C5) having a degree of polymerization of at least 5. 20 In the presence of alkyl esters, methylene bis-benzotriazolyltetramethylbutylphenol in the form of micronized particles having an average particle size ranging from 0.02 to 2 µm, more preferably from 0.01 to 1.5 µm, and more particularly from 0.02 to 1 µm; bis-ethylhexyloxyphenol methoxyphenyl triazine in its aqueous dispersible form and having the INCI name bis-ethylhexyloxyphenol methoxyphenyl triazine (and) acrylate / methacrylic acid C12-22 alkyl ester copolymer; symmetrical triazine masking agents substituted with naphthyl or polyphenyl groups, particularly 2,4,6-tris(biphenyl)triazine and 2,4,6-tris(biphenyl)triazine, used in micronized form (average particle size of 0.02 to 3 µm), and particularly in aqueous dispersion form.
11. The composition according to any one of claims 8 to 10, wherein the inorganic UV masking agent is selected from coated or uncoated titanium dioxide pigments.
12. The composition according to any one of claims 1 to 11, wherein the total amount of the additional UV shielding agent is less than or equal to 20% by weight of the total weight of the composition, preferably less than or equal to 10% by weight, and even more preferably less than or equal to 5% by weight.
13. The composition according to any one of claims 1 to 12, wherein the only UV masking agent present in the composition is a water-soluble organic masking agent and cyanine of formula (3).
Citation Information
Patent Citations
DC motor servo system
CA904392A
cosmetic and dermatological light protection formulations containing bis-resorcinyltriazine derivatives and benzoxazole derivatives
DE10162844A1
Oil-in-water or multiple emulsion with high concentration of suspended UVB filter
DE19726184A1
Use of 4,4-di:aryl-butadiene derivatives as photostable UV filter compounds
DE19746654A1
Use of 4,4-diarylbutadienes as photostable UV filters in cosmetics
DE19755649A1