WO2024002698A1

WO2024002698A1 - Cosmetic composition of liquid crystal lipid particles for improved antioxidant effects

Info

Publication number: WO2024002698A1
Application number: PCT/EP2023/065960
Authority: WO
Inventors: Dong Ryeol Lee; Xue ZHANG; Xiao Yue WANG; Zhi RAO; Di SHEN
Original assignee: Basf Se; Basf (China) Company Limited
Priority date: 2022-07-01
Filing date: 2023-06-14
Publication date: 2024-01-04

Abstract

The presently claimed invention relates to liquid crystal lipid particles. The presently claimed invention relates to liquid crystal lipid particles which are used in topical composition for improving antioxidant effect, in particular for prevention or inhibition of free radical-induced effects on the skin.

Description

Cosmetic Composition of Liquid Crystal Lipid Particles for Improved Antioxidant Effects

Field of the invention

The presently claimed invention relates to liquid crystal lipid particles. In particular, the presently claimed invention relates to liquid crystal lipid particles which are used in topical compositions for improved antioxidant effects.

Background of the invention

In the area of cosmetics, it is believed that the smaller particles are readily absorbed into the skin and repair damage easily and more efficiently. Incorporation of nanotechnology in cos- meceuticals is aimed at making the incense of perfumes last longer, sunscreens to protect the skin, antiaging creams to fight back the years, and moisturizers to maintain the hydration of skin. Some of the nanotechnology-based innovations are nanoemulsions (which are transparent and have unique tactile and texture properties), nanocapsules (which are used in skin care products), nanopigments (that are transparent and increase the efficiency of sunscreen products), liposome formulations (which contain small vesicles consisting of conventional cosmetic materials that protect oxygen or light sensitive cosmetic ingredients), niosomes, nanocrystals, solid lipid nanoparticles, carbon nanotubes, fullerenes, and dendrimers. The primary advantages of using nanoparticles in cosmeceuticals include improvement in the stability of cosmetic ingredients (e.g., vitamins, unsaturated fatty acids, and antioxidants) by encapsulating within the nanoparticles; efficient protection of the skin from harmful ultraviolet (UV) rays; aesthetically pleasing products (e.g., in mineral sunscreens, using smaller particles of active mineral allows them to be applied without leaving a noticeable white cast); targeting of active ingredient to the desired site and controlled release of active ingredients for a prolonged effect.

US 2009/0239956 A1 relates to lamellar liquid crystal compositions for cosmetic use which contain one or more polyglycerol monoethers each having a specific structure, and which are used to remove makeup and cosmetics containing the cosmetic compositions.

WO 2016/003118 A1 relates to a multi-phase cosmetic composition comprising cholesterol liquid crystals resulting in an improvement in the use feeling.

Skin undergoes changes such as becoming thinner, more easily damaged and less elastic. In addition, lifetime exposure to UV-A and UV-B radiation, together with other environmental factors that induce the formation of free radicals, such as pollution from traffic fumes, ozone, cigarette smoke etc, causes additional changes to the skin. These changes, including lines and wrinkling, actinic lentigines, dyspigmentation, rough skin, actinic telangiectasia and further loss of skin elastic function are due to direct UV-mediated damage to cells and indirectly mediated damage caused by the generation of free radicals in cells and tissues. This is generally termed photoageing and can account for up to 90% of the skin changes we associate with ageing. Free radical damage can cause deterioration of the supportive connective tissues resulting in decreased elasticity and resilience. Exposure of skin to solar ultraviolet radiation starts photochemical reactions in the skin leading to reactive oxygen species formation. Sun damage produces both skin cancers as well as photo-ageing which shows itself on the skin as wrinkling, scaling, dryness and mottled pigmentation. Antioxidants play an important part in protective and repair mechanisms within the skin. The deleterious effects of UV radiation are generally believed to be due to the creation of free radicals. These highly reactive species may react with and damage DNA molecules in the skin (or elsewhere). Similar effects can also be attributed to radiation in the visible part of the spectrum.

Thus, there remains a need to provide a cosmetic or skin care composition which may effectively lead to improved antioxidant effects, more particularly, the composition is suitable for being used for the prevention or inhibition of free radical-induced effects on the skin.

Summary of the invention

Surprisingly, it was found that the liquid crystal lipid particles of the present invention are effective in improving antioxidant effects. Particularly, in improving the prevention or inhibition of free radical-induced effects on the skin.

Hence, the present invention relates to the use of a liquid crystal lipid particles for improved antioxidant effects, in particular for prevention or inhibition of free radical-induced effects on the skin.

The liquid crystal lipid particles of the present invention comprise the compounds (I) to (V),

(I) at least one compound of the general formula (I),

general formula (I), wherein m is an in the range from > 10 to < 24 and n is an integer in the range from >1 to < 25,

(II) at least one compound of the general formula (II),

general formula (II), wherein a is an in the range from > 10 to < 24,

(III) at least one compound of the general formula (III),

general formula (III), wherein x is an in the range from > 10 to < 24 and y is an integer in the range from >10 to < 25,

(IV) at least one compound of the general formula (IV),

general formula (IV), wherein p is an in the range from > 10 to < 16. and (V) at least one anionic surfactant selected from the group consisting of alkyl glutamate surfactant, alkyl sulfosuccinate surfactant and alkyl phosphate surfactant.

In another aspect, the present invention relates to a topical composition which comprises the liquid crystal lipide particles as defined hereinabove and at least one UV filter. The combination of the liquid crystal lipid particles and the at least one UV filter would lead to a synergy effect on improvement of antioxidant effect, in particular on prevention or inhibition of free radical-induced effects on the skin. Detailed description of the invention

Before the present compositions and formulations of the presently claimed invention are described, it is to be understood that this invention is not limited to particular compositions and formulations described, since such compositions and formulation may, of course, vary. It is also to be understood that the terminology used herein is not intended to be limiting, since the scope of the presently claimed invention will be limited only by the appended claims.

If hereinafter a group is defined to comprise at least a certain number of embodiments, this is meant to also encompass a group which preferably consists of these embodiments only. Furthermore, the terms 'first', 'second', 'third' or 'a', 'b', 'c', etc. and the like in the description and in the claims, are used for distinguishing between similar elements and not necessarily for describing a sequential or chronological order. It is to be understood that the terms so used are interchangeable under appropriate circumstances and that the embodiments of the presently claimed invention described herein are capable of operation in other sequences than described or illustrated herein. In case the terms 'first', 'second', 'third' or '(A)', '(B)' and '(C)' or '(a)', '(b)', '(c)', '(d)', 'i', 'ii' etc. relate to steps of a method or use or assay there is no time or time interval coherence between the steps, that is, the steps may be carried out simultaneously or there may be time intervals of seconds, minutes, hours, days, weeks, months or even years between such steps, unless otherwise indicated in the application as set forth herein above or below.

Furthermore, the ranges defined throughout the specification include the end values as well i.e. a range of 1 to 10 implies that both 1 and 10 are included in the range. For the avoidance of doubt, applicant shall be entitled to any equivalents according to applicable law.

In the following passages, different aspects of the presently claimed invention are defined in more detail. Each aspect so defined may be combined with any other aspect or aspects unless clearly indicated to the contrary. In particular, any feature indicated as being preferred or advantageous may be combined with any other feature or features indicated as being preferred or advantageous.

Reference throughout this specification to 'one embodiment' or 'an embodiment' means that a particular feature, structure or characteristic described in connection with the embodiment is included in at least one embodiment of the presently claimed invention. Thus, appearances of the phrases 'in one embodiment' or 'in an embodiment' in various places throughout this specification are not necessarily all referring to the same embodiment, but may. Furthermore, the particular features, structures or characteristics may be combined in any suitable manner, as would be apparent to a person skilled in the art from this disclosure, in one or more embodiments. Fur- thermore, while some embodiments described herein include some but not other features included in other embodiments, combinations of features of different embodiments are meant to be within the scope of the presently claimed invention, and form different embodiments, as would be understood by those in the art. For example, in the appended claims, any of the claimed embodiments can be used in any combination

“Topical application” means to apply or spread a composition directly onto the surface of the skin of a human or animal body, preferably onto the face, scalp, feet, limbs or trunk. Particularly to the present invention, the topical application preferably means a cosmetic or skin care composition.

The presently claimed invention relates to the use of a liquid crystal lipid particles in cosmetic or skincare compositions for improving antioxidant effects, in particular, for the prevention or inhibition of free radical-induced effects on the skin.

The liquid crystal lipid particles of the presently claimed invention comprises the compounds (I) to (V), comprising,

(I) at least one compound of the general formula (I):

(II) at least one compound of the general formula (II):

general formula (II), wherein a is an in the range from > 10 to < 24,

(III) at least one compound of the general formula (III):

(IV) at least one compound of the general formula (IV):

general formula (IV), wherein p is an in the range from > 10 to < 16, and (V) at least one anionic surfactant selected from the group consisting from alkyl glutamate surfactant, alkyl sulfosuccinate surfactant and alkyl phosphate surfactant, wherein the alkyl phosphate surfactant is selected from C12-C20 alkyl phosphate, in particular, the alkyl phosphate surfactant can be in the form of, for example, a sodium salt, a potassium salt, ammonium salt or lower alkanolamine (e.g., mono, di and triethanolamine) salt. More particularly, the alkyl phosphate surfactant is selected from the group consisting of potassium cetyl phosphate, potassium lauryl phosphate, and potassium dodecyl phosphate, still more particularly, the alkyl phosphate surfactant is potassium cetyl phosphate; wherein the alkyl glutamate surfactant can be selected from the group consisting of sodium steraroyl glutamate, sodium lauroyl glutamate, sodium cocoyl glutamate, sodium myristoyl glutamate, potassium cocoyl glutamate, potassium lauroyl glutamate, and combinations thereof; wherein the alkyl sulfosuccinate surfactant is C10-C18 alkyl sulfosuccinate, preferably C10-C16 alkyl sulfosuccinate, more preferably C12-C14 alkyl sulfosuccinate.

In a further embodiment of the presently claimed invention, the present invention provides a method for improving antioxidant effects on the skin comprising applying to the skin the liquid crystal lipid particles, in particular, the present invention provides a method for enhancing the prevention or inhibition free radical-induced effect on the skin comprising applying to the skin the liquid crystal lipid particles.

In another embodiment of the present invention, the topical composition of the present invention comprises at least one liquid crystal lipid particles as defined above and at least one UV filter. In a further embodiment of the presently claimed invention, the present invention provides a method for improving antioxidant effects on the skin comprising applying the topical composition comprising at least one liquid crystal lipid particles and at least one UV filter on the skin, in particular, the present invention provides a method for enhancing the prevention or inhibition free radical-induced effect on the skin comprising applying the topical composition comprising at least one liquid crystal lipid particles and at least one UV filter on the skin.

In an embodiment of the presently claimed invention, the liquid crystal lipid particles comprise at least one compound represented by the general formula (I)

general formula (I), wherein m is an in the range from > 10 to < 24 and n is an integer in the range from >1 to < 25.

In an embodiment of the presently claimed invention, the at least one compound of general formula (I) is selected from the group consisting of ceteareths, polyoxyethylene stearyl ether, and polyoxyethylene cetyl ether.

In an embodiment of the presently claimed invention, the at least one compound of general formula (I) is selected from the group consisting of ceteareth-12, ceteareth-20, ceteareth-30.

In a most preferred embodiment of the presently claimed invention, the at least one compound of general formula (I) is selected from the group consisting of ceteareth-12, ceteareth-20.

In an embodiment of the presently claimed invention, in the at least one compound of general formula (II,)

general formula (II), a is an in the range from > 10 to < 24,

In an embodiment of the presently claimed invention, the at least one compound of general formula (II) is selected from the group consisting of glyceryl stearate, glyceryl laurate and glyceryl palmitate, glyceryl caprylate, glyceryl myristate. In a preferred embodiment of the presently claimed invention, the at least one compound of general formula (II) is glyceryl stearate.

In an embodiment of the presently claimed invention, in the at least one compound of general formula (III),

general formula (III), x is an in the range from > 10 to < 24 and y is an integer in the range from >10 to < 25,

In an embodiment of the presently claimed invention, the at least one compound of general formula (III) is selected from the group consisting of myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl myristate, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, isostearyl oleate, oleyl myristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl myristate, behenyl palmitate, behenyl stearate, behenyl isostearate, behenyl oleate, behenyl behenate, behenyl erucate, erucyl myristate, erucyl palmitate, erucyl stearate, erucyl isostearate, erucyl oleate, erucyl behenate and erucyl erucate.

In a further embodiment of the presently claimed invention, the at least one compound of general formula (III) is selected from the group consisting of cetyl palmitate, myristyl myristate, tetra decyl tetra decanoate, and behenyl behenate.

In a preferred embodiment of the presently claimed invention, the at least one compound of general formula (III) is selected from the group consisting of cetyl palmitate, myristyl myristate.

In an embodiment of the presently claimed invention, in the at least one compound of general formula

general formula (IV), p is an in the range from > 10 to < 16. In yet another embodiment of the presently claimed invention, the at least one compound of general formula (IV) is selected from the group consisting of lauryl alcohol, tridecyl alcohol, myristyl alcohol, pentadecyl alcohol, cetyl alcohol, palmitoleyl alcohol, heptadecyl alcohol and stearyl alcohol or mixtures thereof.

In a preferred embodiment of the presently claimed invention, the at least one compound of general formula (IV) is selected from the group consisting of lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol or mixtures thereof.

In a most preferred embodiment of the presently claimed invention, the at least one compound of general formula (IV) is a mixture of cetyl alcohol and stearyl alcohol.

In one embodiment of the present invention, the at least one compound (V) alkyl phosphate surfactant is surfactant is selected from C12-C20 alkyl phosphate, in particular, the alkyl phosphate surfactant can be in the form of, for example, a sodium salt, a potassium salt, ammonium salt or lower alkanolamine (e.g., mono, di and triethanolamine) salt. More particularly, the alkyl phosphate surfactant is selected from the group consisting of potassium cetyl phosphate, potassium lauryl phosphate, and potassium dodecyl phosphate, still more particularly, the alkyl phosphate surfactant is potassium cetyl phosphate.

In an embodiment of the presently claimed invention the crystal lipid particles comprise ce- teareths, glyceryl stearate, cetyl palmitate and/or myristyl myristate, cetyl alcohol, stearyl alcohol and potassium cetyl phosphate.

In an embodiment of the presently claimed invention the crystal lipid particles comprise ce- teareths, glyceryl stearate, myristyl myristate, cetyl alcohol, stearyl alcohol and potassium cetyl phosphate.

In a further embodiment of the presently claimed invention, the liquid crystal lipid particles comprise ceteareths, glyceryl stearate, cetyl palmitate, myristyl myristate, cetyl alcohol, stearyl alcohol and potassium cetyl phosphate.

In a preferred embodiment of the presently claimed invention, the liquid crystal lipid particles comprise ceteareth-12, ceteareth-20, glyceryl stearate, cetyl palmitate, myristyl myristate, cetyl alcohol, stearyl alcohol and potassium cetyl phosphate.

In an embodiment of the presently claimed invention, the liquid crystal lipid particles have an average particle size of > 20 nm to < 500 nm, determined using dynamic light scattering using Malvern DLS ZS90. In an embodiment of the presently claimed invention, the liquid crystal lipid particles have an average particle size of > 20 nm to < 300 nm, determined using dynamic light scattering using Malvern DLS ZS90.

In an embodiment of the presently claimed invention, the liquid crystal lipid particles have an average particle size of > 20 nm to < 150 nm, determined using dynamic light scattering using Malvern DLS ZS90.

In an embodiment of the presently claimed invention, the liquid crystal lipid particles have an average particle size of 20 nm, 30 nm, 40 nm, 50 nm, 60 nm, 70nm, 80 nm, 90nm, 100 nm, 110nm, 120nm, 130 nm, 140nm or 150nm, determined using dynamic light scattering using Malvern DLS ZS90.

In an embodiment of the presently claimed invention, the liquid crystal lipid particles are prepared by using the phase inversion temperature method.

In a further embodiment of the presently claimed invention, the liquid crystal lipid particles are prepared using the phase inversion temperature method as disclosed in D.J. Mitchell et al. Phase behavior of polyoxyethylene surfactants with water. Mesophase structures and partial miscibility (cloud points), J. Chem. Soc. Farayday Trans., 79, 975-1000 (1983) incorporated herein by reference.

In an embodiment of the presently claimed invention, the liquid crystal lipid particles have an orthorhombic lateral packing.

In an embodiment of the presently claimed invention, the liquid crystal lipid particles are included in a topical composition for application to the skin.

In an embodiment of the presently claimed invention, the liquid crystal lipid particles form the base in any topical composition for application to the skin.

In an embodiment of the presently claimed invention, the liquid crystal lipid particle is present in an amount in the range of >1 % to < 30 % by weight, based on the total weight of the topical composition. In a further embodiment of the presently claimed invention, the at least one liquid crystal lipid particle is present in an amount in the range of >1 % to < 25 % by weight, based on the total weight of the composition. In a preferred embodiment of the presently claimed invention, the at least one liquid crystal lipid particle is present in an amount in the range of >1 % to < 20 % by weight, based on the total weight of the composition. In a most preferred embodiment of the presently claimed invention, the at least one liquid crystal lipid particle is present in an amount in the range of >1 % to < 15 % by weight, based on the total weight of the composition In one embodiment of the present invention, the liquid crystal lipid particles of the present invention comprising the compound (I) to (V) is used in combination with at least one UV filter. In one embodiment of the present invention, the method for improving antioxidant effect comprising applying the combination of the liquid crystal lipid particles of the present invention and at least one UV filter on the skin. In one embodiment of the present invention, the method for enhancing the prevention or inhibition of free radical induced effects comprising applying the combination of the liquid crystal lipid particles of the present invention and at least one UV filter on the skin.

The topical composition of the present invention includes at least one or a combined UV filter (also known as UV protective agent), at a concentration, by weight, of greater than 0.5%, or alternatively about 1% to 20 %, or alternatively about 1.5% to 5%, 8%, 10%, 12%, or 15% based upon weight of the composition. Suitable UV filters for the present invention consists of at least one selected from UV absorbing agents and UV scattering agents, which are usually blended in a conventional sunscreen composition. The UV absorbing agents used in the present invention is not specifically limited, and examples thereof include, but not limited to, butyl methoxydibenzoylmethane, ethylhexyl triazone, drometrizole trisiloxane, benzophenone-3, diethylhexyl butamido triazone, bis-ethylhexyloxyphenol methoxyphenyl triazine, 4- methylbenzilidene camphor, and/or benzoxazole compounds, octocrylene, dimethicodiethyl benzalmalonate, polysilicone- 15, t butylmethoxydibenzoylmethane, ethylhexyl triazone, hexyl diethylaminohydroxybenzoylbenzoate, bisethylhexyloxyphenol methoxyphenyl triazine, oxybenzone-3, methylene bis-benzotriazolyl tetramethylbutylphenol, phenylbenzimidazolesulfonic acid, homosalate, and ethylhexyl salicylate. The UV scattering agent used in the present invention is not specifically limited, and examples thereof include fine particles of metal oxides such as zinc oxide, titanium oxide, iron oxide, cerium oxide and tungsten oxide. In some embodiments, the UV filters in the present invention is at least one selected from a UV absorbing agent and a UV scattering agent. In one embodiment, the UV filter of the present invention consists only UV absorbing agent. In other embodiment, the UV filter of the present invention consists only UV scattering agent. Each of the abovementioned UV filter amount in the present invention is represented as the total amount of UV absorbing agent and UV scattering agent, and it is particularly preferred to set the amount of UV absorbing agent to 6 % or more based upon the total weight of the composition.

As examples, UV Filters (also known as UV protective agent) may be designed below under their INCI name:

Dibenzoylmethane Compounds: Butylmethoxydibenzoylmethane sold especially under the tradename Parsol 1789 by DSM Nutritional Products, Inc.; Isopropyldibenzoylmethane.

Para- Aminobenzoic Compounds:

Ethyl PABA,

Ethyl Dihydroxypropyl PABA,

Ethylhexyl Dimethyl PABA sold under the name Escalol 507 by ISP,

Glyceryl PABA

Salicylic Derivatives:

Homosalate sold under the commercial name Eusolex HMS by Rona/EM Industries, Ethylhexyl Salicylate sold under the commercial name Neo Heliopan OS by SYMRISE,

Cinnamic Derivatives:

Ethylhexyl Methoxycinnamate sold under the commercial name ARSOL MCX by DSM

Nutritional Products,

Isopropyl Methoxy cinnamate,

Isoamyl Methoxy cinnamate sold under the commercial name Neo Heliopan E1000 by SYMRISE,

Cinoxate,

Diisopropyl Methylcinnamate,

Derivatives of |3,|3-diphenylacrylate

Octocrylene sold under the commercial name UVINUL N539 by BASF,

Etocrylene sold under the commercial name UVINUL N35 by BASF,

Benzophenone Derivatives:

Benzophenone-1 sold under the commercial name UVINUL 400 by BASF,

Benzophenone-2 sold under the commercial name UVINUL D50 by BASF,

Benzophenone-3 or Oxybenzone, sold under the commercial name UVINUL M40 by BASF,

Benzophenone-6 sold under the commercial name Helisorb 11 by Norquay,

Benzophenone-8 sold under the commercial name Spectra-Sorb UV-24 by American Cyanamid

Benzophenone-12 n-hexyl 2-(4-N,N-diethylamino-2-hydroxybenzoyl)benzoate sold under the commercial name UVINUL A Plus or in the form of mixture with octylmethoxycinnamate under the commercial name UVINUL A Plus B by BASF,

Benzylidenecamphor Derivatives:

3-Benzylidene camphor manufactured under the commercial name MEXORYL SD by CHIMEX,

4-Methylbenzylidene camphor sold under the commercial name EUSOLEX 6300 by MERCK, Polyacrylamidomethyl Benzylidene Camphor manufactured under the commercial name M EXO R YL S W by C H I M EX,

Phenyl Benzotriazole Derivatives:

Drometrizole Trisiloxane sold under the commercial name Silatrizole by RHODIA CHIMIE, Triazine Derivatives

Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine sold under the commercial name Tl NOSORB S by BASF,

Ethylhexyl triazone sold under the commercial name UVINUL T150 by BASF,

Diethylhexyl Butamido Triazone sold under the commercial name UVASORB HEB by SIGMA 3V,

-triazine silicones substituted by two aminobenzoates groups as those described in the patent EP 0841341 , in particular 2,4-bis-(n-butyl 4'-aminobenzalmalonate)-6-[(3-{1 ,3,3,3-tetramethyl-1- [(trimethylsilyloxy]disiloxanyl})propyl)amino]-s-triazine.

Anthranilic Derivatives:

Menthyl anthranilate sold under the commercial name NEO HELIOPAN MA by SYMRISE,

Imidazoline Derivatives:

Ethylhexyl Dimethoxybenzylidene Dioxoimidazoline Propionate,

Benzalmalonate Derivatives:

Di-neopentyl 4'-methoxybenzalmalonate

Polyorganosiloxane with benzalmalonate functions as Polysilicone-15 sold under the commercial name PARSOL SLX by DSM NUTRITIONAL PRODUCTS

Derivatives of 4,4-Diarylbutadiene:

1 , 1-dicarboxy (2,2'-dimethyl-propyl)-4,4-diphenylbutadiene

Benzoxazole Derivatives:

2,4-bis-[5-1 (dimethylpropyl)benzoxazol-2-yl-(4-phenyl)-imino]-6-(2-ethylhexyl)-imino-1 ,3,5- triazine sold under the commercial name Uvasorb K2A by Sigma 3V and mixtures thereof.

Lipophilic Merocyanine Derivatives

-Octyl-5-N,N-diethylamino-2-phenysulfonyl-2,4-pentadienoate and mixtures thereof.

In a preferred embodiment of the presently claimed invention, the UV absorbing agents or sun screen agents are selected from the group consisting of 2-ethylhexyl-p-methoxycinnamate, 4,4'- t-butyl methoxydibenzoyl-methane, 2-hydroxy-4-methoxybenzophenone, octyldimethyl-p- aminobenzoic acid, digalloyltrioleate, 2,2--dihydroxy-4-methoxybenzophenone, ethyl- 4(bis(hydroxypropyl)) aminobenzoate, 2-ethylhexyl-2-cyano-3,3-diphenylacrylate, 2- ethylhexylsalicylate, glyceryl-p-aminobenzoate, 3,3,5-trimethylcyclohexylsalicylate, methylanthranilate, p-dimethyl-aminobenzoic acid or aminobenzoate, 2-ethylhexyl-p-dimethyl-amino- benzoate, 2-phenylbenzimidazole-5-sulfonic acid, 2-(p-dimethylaminophenyl)-5- sulfonicbenzoxazoic acid , Methylene Bis-benzotriazolyl tetramethylbutylphenol and mixtures thereof.

In some preferred embodiments, the topical composition of the present invention comprises the UV protective agent which is selected from the group consisting of Ethylhexyl Methoxycinnamate (Uvinul® MC80), Ethylhexyl Triazone (Uvinul® T150), Methylene Bis- Benzotriazolyl Tetramethylbutylphenol (Tinosorb® M); Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine ( Tinosorb® S ) ; Diethylamino Hydroxybenzoyl Hexyl Benzoate ( Uvinul® A Plus Granular) ; Ethylhexyl Salicylate (Neo Heliopan OS).

The amount of the UV protective agent present in the topical composition is from 0.5 to 30, preferably from 1 to 20% based on the total weight of the composition.

In a preferred embodiment, the topical composition may further comprise additional nonionic, anionic emulsifiers, for example the suitable anionic emulsifier is selected from the group consisting of sodium steraroyl glutamate, sodium lauroyl glutamate, sodium cocoyl glutamate, sodium myristoyl glutamate, potassium cocoyl glutamate, potassium lauroyl glutamate, and combinations thereof.

In an embodiment of the presently claimed invention, the topical composition is present in the form of a cream, a foam, a lotion, a gel, a paste, a spray, a patch, a spray patch, a mousse or an ointment.

In an embodiment of the presently claimed invention, the cosmetic composition further comprises at least one auxiliary agent selected form the group consisting of anti-wrinkle active agents, anti-acne active agents, emulsifiers, antioxidants, emollients, self-tanning active agents, skin lightening agents, sunscreen agents, UV absorbing agents, thickening agents, humectants, abrasives, absorbents, fragrances, buffering agents, opacifying agents, colorants, preservatives, fillers, pH adjusting agents and solvents.

In an embodiment of the presently claimed invention, the active agents are selected from the group consisting of anti-wrinkle agents like retinol, hyaluronic acid, ceramides, niacinamide, vitamin E, alpha hydroxy acids, anti -acne agents like clindamycin, benzamycin, benzoyl peroxide, and isotretinoin. In an embodiment of the presently claimed invention, the skin lightening agents are selected from the group consisting of tretinoin, hydroquinone, resorcinol, arbutin, kojic acid, azelaic acid, vitamin C, glutathione and alpha hydroxy acids.

In an embodiment of the presently claimed invention, the topical composition may further comprise at least one thickening agent. The thickening agents can be selected from the group consisting of polymer thickening agents include non-ionic thickening agents and anionic thickening agents, or mixtures thereof. Suitable non-ionic thickening agents include polyacrylamide polymers, crosslinked poly(N-vinylpyrrolidones), polysaccharides, natural or synthetic gums or polysaccharides, polyvinylpyrrolidone, and polyvinylalcohol. Suitable anionic thickening agents include polyacrylate, acrylic acid/ethyl acrylate copolymers, carboxyvinyl polymers and crosslinked copolymers of alkyl vinyl ethers and maleic anhydride.

In an embodiment of presently claimed invention, the thickening agents are selected from the group consisting of polysaccharides including cellulose, carboxymethyl hydroxyethylcellulose, cellulose acetate propionate carboxylate, hydroxyethylcellulose, hydroxyethyl ethylcellulose, hydroxypropylcellulose, hydroxypropyl methylcellulose, methyl hydroxyethylcellulose, microcrystalline cellulose, sodium cellulose sulfate, and mixtures thereof, natural gums like acacia, agar, alginic acid, ammonium alginate, amylopectin, calcium alginate, calcium carrageenan, carnitine, carrageenan, dextrin, gelatin, gellan gum, guar gum, guar hydroxypropyltrimonium chloride, hectorite, hyaluronic acid, hydrated silica, hydroxypropyl chitosan, hydroxypropyl guar, karaya gum, kelp, locust bean gum, natto gum, potassium alginate, potassium carrageenan, propylene glycol alginate, sclerotium gum, sodium carboxymethyl dextran, sodium carrageenan, tragacanth gum, xanthan gum, and mixtures thereof, preferably the thickening agent is selected from the group consisting of xanthan gum, succinoglycan, gellan gum, pectin, alginates, starches, guars, acrylates, acrylate copolymers, carbomers and associative thickeners. According to any one embodiment of the present invention, the thickening agent is present in an amount in the range of >0.1 % to < 5 % by weight, based on the total weight of the topical composition.

In an embodiment of the presently claimed invention, the humectants are selected from the group consisting sodium 2-pyrrolidone-5-carboxylate (NaPCA), guanidine, glycolic acid and glycolate salts (e.g. ammonium and quaternary alkyl ammonium), lactic acid and lactate salts (e.g. ammonium and quaternary alkyl ammonium), aloe vera in any of its variety of forms (e.g., aloe vera gel), hyaluronic acid and derivatives thereof (e.g., salt derivatives such as sodium hyaluronate), lactamide monoethanolamine, acetamide monoethanolamine, urea, panthenol and derivatives thereof, and mixtures thereof. In an embodiment of the presently claimed invention, the buffering agents are selected from the group consisting of Lactic acid, lactates, gluconic acid, glucono-delta-lactone, sodium gluconate and potassium gluconate, trisodium citrate, tripotassium citrate, sodium lactate and potassium lactate,

In an embodiment of the presently claimed invention, the solvents are selected from the group consisting of Polyhydric alcohol include glycerin, diglycerin, triglycerin, polyglycerin, polypropylene glycol, polyethylene glycol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, 1,3-butylene glycol, 1 ,4-butylene glycol, ethylene glycol monoalkyl ether, diethylene glycol monoalkyl ether, glucose, maltose, sucrose, lactose, xylitose, xylitol, sorbitol, mannitol, maltitol, malbit, panthenol, pentaerythritol, and hyaluronic acid and its salts, water, ethanol and isopropanol.

In an embodiment of the presently claimed invention, the solvents are selected from the group consisting of glycerin, water and ethanol.

In an embodiment of the presently claimed invention, the preservatives are selected from the group consisting of benzalkonium chloride, benzethonium chloride, benzyl alcohol, caprylyl glycol, chlorphenesin, 2,2'-dithiobis(N-methylbenzamide), diazolidinyl urea, ethylenediamine tetraacetic acid, ethylparaben, imidazolidinyl urea, methylparaben, phenoxyethanol, linoleami- dopropyl PG-diammonium chloride phosphate, cocam idopropyl PG-diammonium chloride phosphate, propyl paraben, cis-1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride, dehydroacetic acid or its salts, benzoic acid or its salts, sodium hydroxymethylglycinate and zinc pyrithi- one.

In an embodiment of the presently claimed invention, the liquid crystal lipid particles are included in a topical composition which further comprises sunscreen agents, UV absorbents, thickening agents and solvents.

In a preferred embodiment of the presently claimed invention, the liquid crystal lipid particles are included in a topical composition which further comprises diethylaminohydroxybenzoylhexyl benzoate, ethylhexyl methoxycinnamate, acrylates/beheneth-25 methylacrylate copolymer, methylene Bis-benzotriazolyl tetramethylbutylphenol, decylglucoside, propylene glycol and Xan- than gum, ethanol, water and butylene glycol.

According to any one of the invention embodiments, the topical composition further comprises a carrier, or a mixture of such carriers, which are suitable for application to the skin and/or hair. Suitable carriers for use in topical compositions include water, C1-C6 alcohols, lower alkyl acetate and mixtures thereof. In some embodiments, the carriers can also contain a wide variety of additional materials such as acetone, hydrocarbons such as isobutane, hexane, decene, halogenated hydrocarbons and volatile silicones such as cyclomethicone. In one embodiment, water is present in the topical composition in an amount in the range of >5 % to < 80 % by weight, based on the total weight of the topical composition.

The compositions of the invention are employed in a manner that is appropriate to the intended final use of the product. For example, in the treatment of occasional dry skin due to exposure to weather or other temporary conditions, or in the treatment of occasional skin irritation, the compositions can be used on an as-needed basis until the condition is relieved. When being used to treat a more permanent condition, for example, a condition associated with a defective or deficient lipid barrier, particularly sensitive skin, dry skin associated with any type of aging, or the wrinkling or fine lines associated with a thinning of the stratum corneum with aging, the composition, is preferably applied chronically, to prevent recurrence of the condition.

In an embodiment, the composition of the presently claimed invention can be applied in an amount of from about 0.1 mg/cm² to 2 mg/cm² of skin, from about once per week to about 4 or 5 times daily, preferably from about 3 times a week to about 3 times daily, most preferably about once or twice per day.

Further the composition of the presently claimed invention may be applied for longer duration preferably for a period of at least about one month, from about three months to about twenty years, more preferably from about six months to about ten years, more preferably still from about one year to about five years, thereby resulting in the treatment or prevention of the condition in question.

Examples

The following examples are set forth below to illustrate the methods and results according to the disclosed subject matter. These examples are not intended to be inclusive of all aspects of the subject matter disclosed herein, but rather to illustrate representative methods, compositions, and results. These examples are not intended to exclude equivalents and variations of the presently claimed invention, which are apparent to one skilled in the art.

Materials:

• Emulgade® SE-PF is glyceryl stearate, ceteareth-20, ceteareth-12, Cetearyl alcohol, cetyl palmitate is an emulsifying base, from BASF

• Eumulgin® B1 is ceteareth-12 (cetyl stearyl alcohol with 12 mol EO) which is a non-ionic emulsifier, from BASF

• Cetiol® MM is myristyl myristate which is an emollient, from BASF Eumulgin® SG is sodium steaoryl glutamate which is an anionic emulsifier, from BASF

Amphisol® K: Potassium Cetyl Phosphate from DSM

Uvinul® A Plus is diethylamino hydroxybenzoyl hexyl benzoate which is a UV absorber, from BASF

Tinovis® GTC is acrylates/beheneth-25 methylacrylate copolymer is a thickening agent or a viscosity modifier, from BASF

Tinosorb® M is methylene bis-benzotriazolyl tetramethylbutylphenol, water, decylglucoside, propylene glycol and xanthan gum which is a UV filter, from BASF

Cetiol® Sensoft: Propylheptyl Caprylate, which is an emollient from BASF

Cetiol® B: Dibutyl Adipate, which is an emollient from BASF

Microcare® NB: Sodium Benzoate which is a preservative from Thor

Neo Heliopan OS: Ethylhexyl Salicylate which is a UV filter from Symrise

Tinosorb® S: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine which is a UV filter from BASF

Uvinul® T 150: Ethylhexyl Triazone which is a UV filter from BASF

Cosmedia® SP: Sodium Polyacrylate which is a thickening agent or a viscosity modifier, from BASF

Edeta® BD: Disodium EDTA which is a chelating agent from BASF

Euxyl PE 9010: Phenoxyethanol, Ethylhexylglycerin is a preservative from Ashland.

Orgasol 4000 EXD NAT COS Caresse: Nylon-6/12 is a filler from Arkema orgasol.

Composition of the liquid crystal lipid particles

Process of manufacture:

(1) Heating part A to 86 °C and mixing with stirring till homogeneous

(2) Cooling to 70 °C with stirring and adding part B, dissolve part B until homogeneous (3) Cooling to 40 °C with stirring and adding part C, then part D until homogeneous

Stability of the liquid crystal lipid particle:

The stability of the liquid crystal lipid particle was observed at TO (initial appearance after com- pletion of step (3)) and after storage of 3 months at -20/ 4/ 25/ 40 °C).

Measurement of particle size: Particle size measurement of the liquid crystal lipid particles was done using Malvern DLS ZS90.

There is no significant change of appearance or particle size over 3 months monitoring to con- firm the stability of liquid crystal lipid particle.

Formulations for antioxidant performance test:

Process of manufacturing:

Main mixing(Oil phase Phase A): Adding the Cetiol® Sensoft, Cetiol® B, Uvinul® A Plus, Neo Heliopan OS, Uvinul® T 150 in the main mix vessel, and then heating to 80°C while mixing, until Uvinul® A Plus and Uvinul® T 150 completely dissolved, adding the Cosmedia® SP and dispersed well.

Water phase (Phase B ) : In the premix vessel, adding the Water, demin., Edeta® BD, Eumulg- in® SG, Butylene Glycol heat to 80°C, mixing until dissolved, then adding the Tinovis® GTC UP while mixing, then adding the Pluracare® E 4000 Flakes, Sodium Hydroxide (10% solution) while mixing.

Turning on the homogenizer and adding the Premix B (Water PHASE) to the main mixer (Oil PHASE)

Cooling down to below 40°C, then add the phase C (Tinosorb M) and Phase D (Euxyl PE 9010, Ethanol, Liquid Crystal Lipid Particles, Orgasol 4000 EXD NAT COS Caresse) while mix- ing/homo, then discharge into the storage vessel.

Measurement method for antioxidant performance test: Evaluation of oxidation level:

(1) Sample product is applied on top of sebum film and evaporated until the weight of sebum film will not change any more, this process needs around 1 hour under room temperature.

(2) Samples are exposed in city pollution chamber (same apparatus as described in the patent WO 2019020455 A1 in the name of BASF SE), which is one equipment for simulating the city pollution environment, comprising a diesel engine which generates exhaust gas as the source of air pollution and UV lamps at 340 nm as the source of UV irradiation. By combining both exhaust gas and UV irradiation in the enclosed environment, a highly polluted city environment was simulated. For this test process, samples are polluted with 30 min exhaust gas and together with 2 h UV irradiation.

Test description:

I.Test execution:

1) 1 g of synthetic sebum (e.g., Synthetic Sebum 09D, available from WFK Testgewebe GmbH) is dissolved in 100 ml heptane solvent, using a water bath 15 minutes under 40 °C heat. 2 ml of the sebum solution is added at the center of petri dishes (60 mm diameter x 5 mm height) using an automatic pipette. Then sebum sample is placed in a high ventilated fume hood to evaporate the heptane solvent for 20 mins under room temperature. Then the sebum film samples are built up on the bottom of petri dish. The side walls of the test petri dish samples are wrapped with plastic band seals in order to get them vertically hooked in a position facing the UVA lamps located on sides in the pollution test chamber.

2) Sample product is applied on top of sebum film in petri dish and evaporated for around 1 hour under room temperature in a high ventilated fume hood.

3) Then the petri dish samples are exposed in the pollution chamber, the pollution exposure is simulated as a process of 2h continuous UVA irradiation with 30min diesel engine running. Which means, the diesel engine is turned on at the start at Oh and turned off after 30min, and UVA lamp is turned on at the start at Oh and turned off after 2h. Totally, the sebum samples have been exposed in total to 2 hours of UV irradiation. Although the engine has been generating exhaust gas for 0.5 hour in total, the exposure of the sebum samples to exhaust gas is longer than that, as it does not dissipate from the chamber immediately after the engine has been stopped. After the engine has been turned off, it takes for another about 30 minutes or even longer for the gas to fully dissipate out of the pollution test chamber.

4) After the pollution, taking the polluted sebum samples out. Adding 10ml ethanol into the petri dish and use the parafilm to cover it. The rubber band is used to wrap the parafilm. The petri dish with polluted sebum samples need to be put into the ultrasonic bath for 5mins in order to dissolve the sample film. Then transfer the solution into the brown for future analysis.

4. Malondialdehyde (MDA)- 2-Thiobarbituric acid (TBA) analysis: Malondialdehyde ( DA) react with 2-Thiobarbituric acid (TBA), then quantification with Spectrophotometer.

1) TBA Preparation: Add 0.57g TBA into 100g water to make the TBA solution, (stir at 50°C for at least 30mins)

2) SDS solution preparation: Add 8g Sodium dodecyl sulfate into 92g water to make the 8w% SDS solution.

3) Acetic acid solution preparation: Add 40ml acetic acid into 200ml water to make the 20vol% acetic acid solution.

4) Add 1.5ml 20vol% acetic acid, 0.2ml 8w% SDS, 0.5ml water, 1.5ml TBA solution and 0.3ml polluted sebum sample in the tube. Totally 4ml. Then heating at 95°C in the oil bath for 1h. Cooling in the water bath under room temperature for 10 min.

5) Then detected with Spectrophotometer, UV-vis scan between 200 and 800 nm, Colorimetry: UV detection for DA-TBA complex at 532nm. The MDA level reflected by the absorbance at 532nm. The higher of absorbance, the more MDA generated. The more MDA generated means the more oxidation of sebum, indicating lower antioxidant performance.

Results

The results showed the Examples 1 & 2 demonstrate an improved antioxidant effect, in particular, the Example 2 showed synergist antioxidant effects when the liquid crystal lipid particles of the present invention are used in combination with UV filter.

Claims

1. Use of liquid crystal lipid particles for improving antioxidant effects, in particular for prevention or inhibition of free radical-induced effects on the skin, wherein the liquid crystal lipid particles comprise the compounds (I) to (IV), at least one compound (I) having the general formula (I):

general formula (I), wherein m is an in the range from > 10 to < 24 and n is an integer in the range from >1 to < 25, at least one compound (II) having the general formula (II):

general formula (II), wherein a is an in the range from > 10 to < 24, at least one compound (III) having the general formula (III):

general formula (III), wherein x is an in the range from > 10 to < 24 and y is an integer in the range from >10 to < 25, at least one compound (IV) having the general formula (IV):

2. The use according to claim 1 , wherein the liquid crystal lipid particles have a lamellar structure with orthorhombic lateral packing.

3. The use according to claim 1 , wherein the liquid crystal lipid particles have an average particle size in the range of > 20 nm to < 300 nm, determined using dynamic light scattering using Malvern DLS ZS90.

4. The use according to any one of claims 1 to 3, wherein the at least one compound of general formula (I) is selected from the group consisting of ceteareths, polyoxyethylene stearyl ether, and polyoxyethylene cetyl ether.

5. The use according to any one of claims 1 to 4, wherein the at least one compound of general formula (II) is selected from the group consisting of glyceryl stearate, glyceryl laurate and glyceryl palmitate.

6. The use according to any one of claims 1 to 5, wherein the at least one compound of general formula (III) is selected from the group consisting of cetyl palmitate, myristyl myristate, tetra decyl tetra decanoate, and behenyl behenate.

7. The use according to any one of claims 1 to 6, wherein the at least one compound of general formula (IV) is selected from the group consisting of lauryl alcohol, tridecyl alcohol, myristyl alcohol, pentadecyl alcohol, cetyl alcohol, palmitoleyl alcohol, heptadecyl alcohol, stearyl alcohol or mixtures thereof.

8. The use according to any one of claims 1 to 7, wherein the at least one alkyl phosphate surfactant is selected from C12-C20 alkyl phosphate; preferably the alkyl phosphate surfactant is selected from the group consisting of potassium cetyl phosphate, potassium lauryl phosphate, and potassium dodecyl phosphate, still more particularly, the alkyl phosphate surfactant is potassium cetyl phosphate.

9. The use according to any one of claims 1 to 8, wherein the liquid crystal lipid particles comprise ceteareths, glyceryl stearate, cetyl palmitate and/or myristyl myristate, cetyl alcohol, stearyl alcohol and C12-C20 alkyl phosphate; preferably the liquid crystal lipid particles comprise ceteareths, glyceryl stearate, myristyl myristate, cetyl alcohol, stearyl alcohol and C12-C20 alkyl phosphate.

10. The use according to any one of claims 1 to 9, wherein the liquid crystal lipid particles comprise ceteareths, glyceryl stearate, cetyl palmitate, myristyl myristate, cetyl alcohol, stearyl alcohol and potassium cetyl phosphate.

11. The use according to any one of claims 1 to 10, wherein the liquid crystal lipid particles comprise ceteareth-12, ceteareth-20, glyceryl stearate, cetyl palmitate, myristyl myristate, cetyl alcohol, stearyl alcohol and potassium cetyl phosphate.

12. A topical composition comprising, at least one liquid crystal particle as defined in any one of claims 1 to 11, at least one UV filter.

13. The topical composition according to claim 12, wherein the at least one UV filter agent is selected from the group consisting of 2-ethylhexyl-p-methoxycinnamate, 4,4'-t-butyl methoxydibenzoyl-methane, 2-hydroxy-4-methoxybenzophenone, octyldimethyl-p- aminobenzoic acid, digalloyltrioleate, 2,2-dihydroxy-4-methoxybenzophenone, ethyl- 4(bis(hydroxypropyl)) aminobenzoate, 2-ethylhexyl-2-cyano-3,3-diphenylacrylate, 2- ethylhexylsalicylate, glyceryl-p-aminobenzoate, 3,3,5-trimethylcyclohexylsalicylate, methylanthranilate, p-dimethyl-aminobenzoic acid or aminobenzoate, 2-ethylhexyl-p- dimethyl-amino-benzoate, 2-phenylbenzimidazole-5-sulfonic acid, 2-(p- dimethylaminophenyl)-5-sulfonicbenzoxazoic acid , Methylene Bis-benzotriazolyl tetramethylbutylphenol and mixtures thereof.

14. The topical composition according to claim 12 or 13, wherein the composition further comprises at least one thickening agent, preferably the thickening agent is selected from the group consisting of xanthan gum, succinoglycan, gellan gum, pectin, alginates, starches, guars, acrylates, acrylate copolymers, carbomers and associative thickeners.

15. The topical composition according to any one of claims 12 to 14, wherein the liquid crystal lipid particle is present in an amount in the range of >1 % to < 30 % by weight, based on the total weight of the topical composition.

16. The topical composition according to claim 14 or 15, wherein the at least one thickening agent is present in an amount in the range of >0.1 % to < 5 % by weight, based on the total weight of the topical composition.

17. The topical composition according to any one of claims 12 to 16, wherein water is present in an amount in the range of >5 % to < 80 % by weight, based on the total weight of the topical composition.

18. The topical composition according to any one of claims 12 to 17, which further comprises at least one auxiliary agent selected form the group consisting of anti-wrinkle active agents, anti- acne active agents, emulsifiers antioxidants, emollients, self-tanning active agents, skin lightening agents, sunscreen agents, humectants, abrasives, absorbents, fragrances, buffering agents, opacifying agents, colorants, preservatives, fillers and pH adjusting agents.

19. The topical composition according to any one of claims 12 to 18, wherein the topical composition is a skin care composition.

20. The topical composition according to any one of claims 12 to 19, wherein the topical composition is present in the form of a cream, a foam, a lotion, a gel, a paste or an ointment.

21. A method for improving antioxidant effects comprising applying to the skin at least one liquid crystal lipid particle as defined in any one of claims 1 to 11 or the topical composition according to any one of claims 12 to 20.

22. A method for prevention or inhibition of free radical-induced effects on the skin, comprising applying to the skin at least one liquid crystal lipid particle as defined in any one of claims 1 to 11 or the topical composition according to any one of claims 12 to 20.