WO2014127929A1

WO2014127929A1 - Cosmetic sunscreen having reduced white-cast effect

Info

Publication number: WO2014127929A1
Application number: PCT/EP2014/050582
Authority: WO
Inventors: Yvonne NEUMANN; David SCHLENKER; Andreas B. Kummer
Original assignee: Beiersdorf Ag
Priority date: 2013-02-25
Filing date: 2014-01-14
Publication date: 2014-08-28
Also published as: DE102013203045A1; EP2958632A1

Abstract

The invention relates to a cosmetic preparation, containing a) one or more UV filters, b) a polyglycerol ester, c) octyl-decyl citrate polyesters containing a silicone spacer and derivatives of said octyl-decyl citrate polyesters.

Description

description

Cosmetic sunscreen with reduced whitening effect

The present invention relates to a cosmetic preparation containing one or more UV filters and a silicone spacer containing Octyldecylcitratpolyester and derivatives thereof

The trend away from sophisticated paleness to "healthy, sporty brown skin" has been unbroken for years, and people are exposing their skin to sunlight, as it causes pigmentation in the sense of melanin formation, which has ultraviolet radiation from sunlight In addition to the acute injury (sunburn), long-term damage such as an increased risk of developing skin cancer due to excessive exposure to light from the UVB range (wavelength: 280-320 nm) occurs UVB and UVA radiation (wavelength: 320-400 nm) also leads to a weakening of the elastic and collagen fibers of the connective tissue, which leads to numerous phototoxic and photoallergic reactions and leads to premature aging of the skin.

To protect the skin, therefore, a number of sunscreen filter substances have been developed which can be used in cosmetic preparations. These UVA and UVB filters are summarized in most industrialized countries in the form of positive lists such as Appendix 7 of the German Cosmetics Regulation.

However, the variety of commercially available sunscreens must not obscure the fact that these prior art formulations have a number of disadvantages.

A particular problem is the application of sunscreens (especially if they contain titanium dioxide or zinc oxide as a UV filter) to the wet skin. Usually sunscreen is used in the summer in conjunction with water sports, for example, on the beach or in the pool before, during and after bathing, surfing, sailing or the like. Usually also in so-called

"UV-resistant" sunscreens rinse off a part of the UV filter applied before contact with water during bathing, etc., so that the skin has to be treated again with sunscreen after contact with water in order to be sufficiently protected from UV radiation Application to the then still wet skin usually leads to precipitations and inhomogeneities of the sunscreen, which is expressed by the phenomenon called "white", the formation of white remnants on the skin. This effect is not only unaesthetic. In addition, the protective effect (SPF) also suffers.

On the other hand, it is especially difficult for parents of toddlers to dry them properly after playing in the water and cream with sunscreen, since the little ones like to escape parental care.

It was therefore the object of the present invention to eliminate the deficiencies of the prior art and to develop sunscreens that can be applied without problems or with a reduced whitening effect on the wet skin.

Surprisingly, the object is achieved by a cosmetic preparation comprising a) one or more UV filters b) a polyglycerol ester c) a silicone spacer containing Octyldecylcitratpolyester and derivatives thereof

Although the prior art knows the US 2012/0014882, but this document could not point the way to the present invention, not least because the invention provided with Silikonspacer Octyldecylcitratpolyester and derivatives thereof in combination with polyglycerol esters without carboxylated acrylic copolymer significantly less white.

Embodiments of the present invention which are advantageous according to the invention are characterized in that, in particular, octyldecyl citrate polyester is used with a silicone spacer of the type dialkylsiloxysilicate or dimethicone.

Another preferred embodiment of the present invention is thereby

in that the following structure is used as silicone spacer:

For example, such compounds of octyldecyl citrate polyester can be obtained from SurfaTech Corporation in the Cosmosurf series. The polyglycerol ester is also described by SurfaTech Corporation as Cosmosurf PG 1 IS.

It is inventively advantageous if the preparation contains one or more UV filters selected from the group of compounds 2-phenylbenzimidazole-5-sulfonic acid and / or salts thereof; Phenylene-1,4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid salts; 1,4-di (2-oxo-10-sulfo-3-bomylidenemethyl) benzene and its salts; 4- (2-oxo-3-bomylidene-methyl) benzenesulfonic acid salts; 2-methyl-5- (2-oxo-3-bornylidenemethyl) sulfonic acid salts; 2,2'-methylene-bis (6- (2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethylbutyl) -phenol); 2- (2H-benzotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1,3,3,3-tetramethyl-1 - [(trimethylsilyl) oxy] disiloxanyl] propyl] -phenol; 3- (4-methylbenzylidene) camphor; 3-benzylidenecamphor;

ethylhexyl salicylate; Terephthalidendicamphersulfonsäure; 4- (tert-butyl) -4'-methoxydibenzoylmethane;2-ethylhexyl-2-cyano-3,3-diphenylacrylate; 2-ethylhexyl 4- (dimethylamino) benzoate; 4- (dimethylamino) benzoic acid amyl ester; Di (2-ethylhexyl) 4-methoxybenzalmalonate; 4-methoxycinnamate (2-ethylhexyl) ester; 4-methoxycinnamic acid isoyl ester; 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone;2,2'-dihydroxy-4-methoxybenzophenone; Hexyl 2- (4'-diethylamino-2'-hydroxybenzoyl) benzoate; homomenthyl; 2-ethylhexyl 2-hydroxybenzoate; dimethicodiethylbenzalmalonate; 3- (4- (2,2-bisethoxycarbonylvinyl) -phe- noxy) propenyl) methoxysiloxane / dimethylsiloxane copolymer; Dioctylbutylamidotriazone (INCI: diethylhexyl-butamidotriazone); 2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2-yl- (4-phenyl) -imino] -6- (2-ethylhexyl) -imino-1,3,5-triazine having the (CAS Nos 288254-16-0); 4,4 ', 4 "- (1,3,5-triazine-2,4,6-triyltriimino) tris-benzoic acid tris (2-ethylhexyl ester) (also: 2,4,6-tris [anilino] (p-carbo-2'-ethyl-1'-hexyloxy)] - 1, 3,5-triazine (INCI: ethylhexyl triazone); 2,4-bis - {[4- (2-ethylhexyloxy) -2 -hydroxy] -phenyl} -6- (4-methoxyphenyl) -1, 3,5-triazine; 2,4,6-tribiphenyl-4-yl-1,3,5-triazine; merocyanines.

These can be used in a total amount of 0.1-40% by weight, based on the

Total weight of the preparation to be included in this.

In addition, according to the invention, the preparation according to the invention may advantageously contain further ingredients.

According to the invention, the composition according to the invention advantageously contains one or more humectants (moisturizers). Moisturizers are substances or mixtures of substances which, when applied or spread on the surface of the skin, confer the property on cosmetic preparations

Moisturizing the horny layer (also called transepidermal water loss (TEWL) called) and / or to influence the hydration of the horny layer positively.

Advantageous humectants (moisturizers) for the purposes of the present invention are, for example, glycerol, lactic acid and / or lactates, in particular sodium lactate,

Butylene Glycol, Propylene Glycol, Biosaccaride Gum-1, Hydroxyethylurea, Glycine Soy, Ethylhexyloxyglycerol, Pyrrolidonecarboxylic Acid, Glyceryl Glucose Quaternary Compounds, Alkanediols and Urea. Furthermore, it is particularly advantageous to use polymeric moisturizers from the group of water-soluble and / or water-swellable and / or water-gellable polysaccharides. Hyaluronic acid, chitosan and / or a fucose-rich polysaccharide, for example, which are filed in the Chemical Abstracts under the registry number 178463-23-5 and z. B. under the name Fucogel®1000 from the company SOLABIA S.A. is available.

It is advantageous for the purposes of the present invention, when the inventive

Preparation one or more humectants in a total concentration of 0, 1 to 20% by weight and preferably in a total concentration of 0.5 to 15% by weight, each based on the total weight of the preparation contains. The cosmetic preparations according to the invention may also advantageously, although not necessarily, contain fillers which are e.g. B. further improve the sensory and cosmetic properties of the formulations and, for example, cause or enhance a velvety or silky feel on the skin. Advantageous fillers for the purposes of the present invention are starch and starch derivatives (such as, for example, tapioca starch,

Distarch phosphate, polysilsesquioxanes, siloxane elastomers, aluminum or sodium starch octenylsuccinate and the like), pigments which have neither primarily a UV filter effect nor a coloring effect (such as. For example, boron nitride etc.), polyethylene, nylon, aerosils ^® (CAS No. 7631-86-9) and / or talc.

According to the invention, it is preferred if the preparation contains fillers, in particular

Polyethylene, nylon, natural or modified starches such as tapioca starch and / or silicates such as talc.

The oil phase of the formulations according to the invention is advantageously selected from the group of polar oils, for example from the group of lecithins and fatty acid triglycerides, namely the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 8 to 24, in particular 12 to 18 carbon atoms. The fatty acid triglycerides can be selected, for example, advantageously from the group of synthetic, semi-synthetic and natural oils, such as. Coco glyceride, olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, argan oil, almond oil, palm oil, coconut oil, castor oil, wheat germ oil, grape seed oil, thistle oil, evening primrose oil, macadamia nut oil and the like.

Also advantageous according to the invention are z. As natural waxes of animal and vegetable origin, such as beeswax and other insect waxes and berry wax, shea butter and / or lanolin (wool wax).

In the context of the present invention, further advantageous polar oil components can furthermore be selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of from 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or or unbranched alcohols having a chain length of 3 to 30 carbon atoms and from the group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 carbon atoms. Such ester oils can then advantageously be selected from the group octyl palmitate, octyl cocoate, octyl isostearate, octyl dodecyl myristate, octyl dodecanol, cetearyl isononanoate, isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isoctyl stearate, isononyl stearate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, 2-octyl dodecyl palmitate, stearyl heptanoate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate, tridecyl stearate, tridecyl trimellitate, as well as synthetic, semi-synthetic and natural mixtures of such esters, such as. B. jojoba oil.

Furthermore, the oil phase can be advantageously selected from the group of dialkyl ethers and dialkyl carbonates, advantageous z. B. dicaprylyl ether (Cetiol OE) and / or Dicaprylyl- carbonate, for example, that available under the trade name Cetiol CC in the company. Cognis.

It is further preferred that the oil components are selected from the group isoeicosane, neopentyl glycol diheptanoate, propylene glycol dicaprylate / dicaprate, caprylic / capric / diglyceryl succinate, butylene glycol dicaprylate / dicaprate, cocoglycerides (eg Myritol® 331 from Henkel), C ₁ 2-13- alkyl lactate, di-C _12- 13 alkyl tartrate, triisostearin, Dipentaerythrityl Hexacaprylat / Hexacaprat, Propylenglykolmonoisostearat, tricaprylin, dimethyl isosorbide. It is particularly advantageous if the oil phase of the formulations of the invention has a content of C ₁ 2-15 alkyl benzoate or consists entirely of this.

Advantageous Olkomponenten are also z. Butyloctyl salicylate (for example that available under the trade name Hallbrite BHB from the company CP Hall), hexadecyl benzoate and butyl octyl benzoate and mixtures thereof (Hallstar AB) and / or diethylhexylnaphthalate (Hallbrite TQ from CP Hall or Corapan®TQ from Haarmann & Reimer).

The cosmetic preparations according to the invention may also advantageously, although not necessarily, contain fillers which are e.g. B. further improve the sensory and cosmetic properties of the formulations and, for example, cause or enhance a velvety or silky feel on the skin. Advantageous fillers for the purposes of the present invention are starch and starch derivatives (such as, for example, tapioca starch,

Distarch phosphate, aluminum or sodium starch, octenyl succinate, and the like), pigments which have neither primary UV filtering nor coloring action (such as e.g.

Boron nitride, etc.), polyethylene, nylon, aerosils ^® (CAS-No. 7631 -86-9) and / or talc.

Polyethylene, nylon, natural or modified starches such as tapioca starch and / or silicates such as talc. Any mixtures of such oil and wax components are also advantageous to use in the context of the present invention.

Furthermore, the oil phase may also advantageously contain nonpolar oils, for example those which are selected from the group of branched and unbranched hydrocarbons and waxes, in particular mineral oil, Vaseline (petrolatum), paraffin oil, squalane and squalene, polyolefins, hydrogenated polyisobutenes and isohexadecane. Among the polyolefins, polydecenes are the preferred substances.

Advantageously, the oil phase may further comprise a content of cyclic or linear silicone oils or consist entirely of such oils, although it is preferred to use an additional content of other oil phase components in addition to the silicone oil or the silicone oils.

Silicone oils are high molecular weight synthetic polymeric compounds in which silicon atoms are linked in chain and / or net fashion via oxygen atoms and the remaining valencies of silicon are linked by hydrocarbon radicals (usually methyl, more rarely ethyl, propyl, phenyl groups, etc.) are saturated. Systematically, the silicone oils are called polyorganosiloxanes. The methyl-substituted polyorganosiloxanes, which are the quantitatively most important compounds of this group and are characterized by the following structural formula

are also referred to as polydimethylsiloxane or dimethicone (INCI). Dimethicones are available in different chain lengths or with different molecular weights.

Particularly advantageous polyorganosiloxanes in the context of the present invention are, for example, dimethylpolysiloxanes [poly (dimethylsiloxane)], which are obtainable, for example, under the trade names Abil 10 to 10 000 from Th. Goldschmidt. Also advantageous are phenylmethylpolysiloxanes (INCI: phenyl dimethicone, phenyl trimethicone), cyclic silicones (octamethylcyclotetrasiloxane or decamethylcyclopentasiloxane), which are also referred to as cyclomethicones according to INCI, amino-modified silicones (INCI: amodimethicones) and silicone waxes, eg. As polysiloxane-polyalkylene copolymers (INCI: stearyl dimethicone and cetyl dimethicone) and dialkoxydimethylpolysiloxanes (stearoxy dimethicone and behenoxy stearyl dimethicone), which as different Abil-Wax types available from Th. Goldschmidt. However, other silicone oils are also advantageous for the purposes of the present invention, for example cetyl dimethicone, hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane).

The preparations according to the invention may advantageously contain cosmetic active ingredients.

It is inventively preferred if the preparation one or more

Active ingredients selected from the group of compounds glycyrrhetinic acid, urea, arctiin, alpha-lipoic acid, folic acid, phytoene, D-biotin, coenzyme Q10, alpha-glucosylrutin, carnitine, carnosine, caffeine, natural and / or synthetic isoflavonoids, glyceryl glucose, creatine, creatinine , Taurine, β-alanine and / or licochalcone A.

It is inventively advantageous if the preparation of methyl paraben, ethylparaben, propylparaben, Piroctone olamine, dehydroacetic acid, organic acids such as, sorbic acid, benzoic acid, salicylic acid and its salts, Formaldehydabspalter, organic halides, such as IPBC, ethyl lauroylarginate, quaternary

Compounds such as benzalkonium chloride, cetrimonium chloride or bromide or benzethone chloride, silver and silver compounds, 2-methylisothiazol-3 (2H) -one and / or phenoxyethanol.

The use of methylparaben, ethylparaben, propylparaben, 2-methylisothiazol-3 (2H) -one and / or phenoxyethanol is preferred according to the invention

Embodiments which are advantageous according to the invention are characterized in that the preparation comprises ethanol, propylene glycol, butylene glycol, 2-methylpropane-1,3-diol, 1, 2-pentanediol, 1, 2-hexanediol, 1, 2-octanediol and / or 1, 2 Decanediol, ethylhexylglycerol, glyceryl caprylates, hydroxamic acids, chelating agents.

The use of propylene glycol, butylene glycol, 2-methylpropane-1, 3-diol, 1, 2-pentanediol, 1, 2-hexanediol, 1, 2-octanediol and / or 1, 2-decanediol is preferred according to the invention

The preparation according to the invention can advantageously be used for day care or as sunscreen, without being limited to these fields of application.

It is advantageous according to the invention if the preparation is applied in the form of a spray. Not least according to the invention is the use of an inventive

Octyldecyl citrate polyesters and their derivatives in combination with polyglycerol esters without carboxylated acrylic copolymer to reduce whitening when applying sunscreens to the wet skin.

Verqleichsversuche

The diminished whitening effect was evaluated by means of a contrast measurement "BNdanaltytic method for object segmentation based on gray scale gradients for determination of the degree of coverage of product to skin"

Whiteness of the compound was determined by pixel measurement by the ImageJ program.

The areas to be examined were segmented with manual adjustment of the threshold and then the degree of coverage was calculated absolutely.

The absolute calculation shows that a whitening effect was greatly reduced by the invention described here. The absolute pixel contrast gives the reference sample a significantly higher value than the new formulation (BSP1).

Examples:

The following examples are intended to illustrate the present invention without limiting it. Unless indicated otherwise, all amounts, proportions and percentages are based on the weight and the total amount or on the total weight of the preparations.

BSP 1 BSP 2 BSP 3 BSP 4 BSP 5 BSP 6 BSP 7 BSP 8

INCI m [%] m [%] m [%] m [%] m [%] m [%] m [%] m [%]

Dibutyl Adipate 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0

Paraffin Liquidum 2,4

Isohexadecane 2,4 1,5 2,4

C12-15 alkyl benzoates 9.5 9.5 9.5 9.5 9.5 9.5 9.5 9.5

Squalane 2,4

Butylene Glycol 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 Dicaprylates / Dicaprate

C13-16 isoparaffin 2,4 1,5 2,4

Butyl Methoxydibenzoyl- 4,5 4,5 4,5 4,5 4,5 4,5 4,5 4,5 methane

Ethyl hexyl salicylates 4.5 4.5 4.5 4.5 4.5 4.5 4.5 4.5

Octocrylene 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0

Homosalates 9.0 9.0 9.0 9.0 9.0 9.0 9.0 9.0

Polysilicone-15 1.0 1.0 1.0 1.0 1.0 1.0

Bis-ethylhexyloxyphenol 2.0 2.0 2.0 2.0 2.0 2.0

Methoxyphenyl triazines

Glycerine (99%) 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5

Octyldodecyl Citrate 9.5 6.0 9.5 6.0 9.5 9.5 9.5 9.5 Crosspolymer

Cosmosurf PG-IS 2.0 2.0 2.0 2.0 2.0 2.0 2.0 1.0

Alcohol Denat. absolute 37.4 41.8 37.4 41.8 37.4 37.4 40.4 40.4 (100%)

Perfume 0.7 0.7 0.7 0.7 0.7 0.7 0.7 0.7

Totals: 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0

Claims

claims

1 . Contains cosmetic preparation

a) one or more UV filters

b) a polyglycerol ester

c) a silicone spacer containing Octyldecylcitratpolyester and derivatives thereof

2. Cosmetic preparation according to one of the preceding claims, characterized

in that the following structure is used as silicone spacer:

3. Cosmetic preparation according to one of claims 1 or 2, characterized

in that the following structure is used as silicone spacer:

4. Cosmetic preparation according to one of the preceding claims, characterized

in that the preparation contains one or more UV filters selected from the group of the compounds 2-phenylbenzimidazole-5-sulphonic acid and / or salts thereof; Phenylene-1,4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid salts; 1,4-di (2-oxo-10-sulfo-3-bomylidenemethyl) benzene and its salts; 4- (2-oxo-3-bornylidenemethyl) benzenesulfonic acid salts; 2-methyl-5- (2-oxo-3-bomylidenemethyl) sulfonic acid salts; 2,2'-methylenebis (6- (2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethylbutyl) phenol); 2- (2H-Benzotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1,3,3,3-tetramethyl-1 - [(trimethylsilyl) oxy] disiloxanyl] propyl] -phenol; 3- (4-methylbenzylidene) camphor; 3-benzylidene camphor; ethylhexyl salicylate; Terephthalidendicamphersulfonsäure; 4- (tert-butyl) -4'-methoxydibenzoylmethane;2-ethylhexyl-2-cyano-3,3-diphenylacrylate; 2-ethylhexyl 4- (dimethylamino) benzoate; 4- (dimethylamino) benzoic acid amyl ester; 4-Methoxybenzalmalon-säuredi (2-ethylhexyl) ester; 4-methoxycinnamic acid (2- ethylhexyl ester); Isoamyl 4-methoxycinnamate; 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone;2,2'-dihydroxy-4-methoxybenzophenone; 2- (4'-diethylamino-2'-hydroxybenzoyl) benzoic acid hexyl ester; homomenthyl; 2-ethylhexyl 2-hydroxybenzoate; dimethicodiethylbenzalmalonate; 3- (4- (2,2-ethoxycarbonylvinyl) phenoxy) propenyl) methoxysiloxane / dimethylsiloxane copolymer;

Dioctylbutylamidotnazone (INCI: diethylhexylbutamidotriazone); 2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2-yl- (4-phenyl) -imino] -6- (2-ethylhexyl) -imino-1,3,5-triazine with the CAS No. 288254-16-0); 4,4 ', 4 "- (1,3,5-triazine-2,4,6-triyltriimino) tris-benzoic acid tris (2-ethylhexyl ester) (also: 2,4,6-tris [anilino - (p-carbo-2'-ethyl-1'-hexyloxy)] - 1, 3,5-triazine (INCI: ethylhexyl triazone); 2,4-bis - {[4- (2-ethyl-hexyloxy) -] 2-hydroxy] -phenyl} -6- (4-methoxyphenyl) -1, 3,5-triazine; 2,4,6-tribiphenyl-4-yl-1,3,5-triazine; contains merocyanines.

5. Cosmetic preparation according to one of the preceding claims, characterized

in that the preparation contains one or more active substances selected from the group of compounds glycyrrhetinic acid, urea, arctiin, alpha-lipoic acid, folic acid, phytoene, D-biotin, coenzyme Q10, alpha-glucosylrutin, carnitine, carnosine, caffeine, natural and / or synthetic isoflavonoids, glyceryl glucose, creatine, creatinine, taurine, β-alanine and / or licochalcone A.

6. Cosmetic preparation according to one of the preceding claims, characterized

in that the preparation contains methylparaben, ethylparaben, propylparaben, 2-methylisothiazol-3 (2H) -one and / or phenoxyethanol.

7. Cosmetic preparation according to one of the preceding claims, characterized

in that the preparation contains propylene glycol, butylene glycol, 2-methylpropane-1, 3-diol, 1, 2-pentanediol, 1, 2-hexanediol, 1, 2-octanediol and / or 1, 2-decanediol.

8. Cosmetic preparation according to one of the preceding claims, characterized

in that the preparation contains the silicone spacer-containing oligomer in a total concentration of 0, 1 to 5% by weight, based on the

Total weight of the preparation contains.

9. Cosmetic preparation according to one of the preceding claims, characterized

in that the preparation is a polyglycerol ester in a total concentration of 0.1 to 2% by weight, based on the total weight of the preparation.

10. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation is applied in the form of a spray.