AU2017239586A1 - Ethanolic sunscreen agent with reduced tendency to stain textiles - Google Patents

Ethanolic sunscreen agent with reduced tendency to stain textiles Download PDF

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Publication number
AU2017239586A1
AU2017239586A1 AU2017239586A AU2017239586A AU2017239586A1 AU 2017239586 A1 AU2017239586 A1 AU 2017239586A1 AU 2017239586 A AU2017239586 A AU 2017239586A AU 2017239586 A AU2017239586 A AU 2017239586A AU 2017239586 A1 AU2017239586 A1 AU 2017239586A1
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Prior art keywords
inci
sunscreen agent
preparation
oil
use according
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AU2017239586A
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Kathrin BORCHERS
Anja Eisert
Shimoda Toshihiko
Stephanie Von Der Fecht
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Beiersdorf AG
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Beiersdorf AG
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4966—Triazines or their condensed derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/26—Optical properties
    • A61K2800/262—Transparent; Translucent

Abstract

Abstract An ethanolic cosmetic sunscreen agent comprising: a) one or more UV filters selected from the group consisting of the compounds 4-(tert.-butyl)-4' methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoylmethane), (2-[-4-(diethylamino)-2 hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine); b) ethanol in a minimum quantity of 10 wt%, relative to the total weight of the preparation; and c) one or more oil components having a contact angle greater than/equal to 44'. Also, a method and use of one or more oil components having a contact angle greater than/equal to 44' to protect against textile staining.

Description

TECHNICAL FIELD
The present invention relates to an ethanolic cosmetic sunscreen agent comprising:
a) one or more UV filters selected from the group consisting of the compounds 4-(tert.-butyl)-4’methoxydibenzoylmethane (INCI Butyl Methoxydibenzoylmethane), (2-[-4-(diethylamino)-2hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine);
b) ethanol in a minimum quantity of 10 wt%, relative to the total weight of the preparation; and
c) one or more oil components having a contact angle greater than/equal to 44°, as well as to a method and use of one or more oil components having a contact angle greater than/equal to 44° to protect against textile staining.
BACKGROUND ART
The trend away from genteel pallor towards “healthy, athletic tanned skin” has been unbroken for years. In order to attain this, people expose their skin to solar radiation, since this brings about pigment formation in the sense of melanin formation. However, the ultraviolet radiation of sunlight also has a harmful effect on the skin. Besides acute damage (sunburn), long-term damage occurs, such as suffering from an increased risk of skin cancer in cases of excessive irradiation with light from the UVB region (wavelength: 280-320 nm). Moreover, the excessive effect of UVB and UVA radiation (wavelength: 320-400 nm) leads to a weakening of the elastic and collagenous fibers of connective tissue. This leads to numerous phototoxic and photoallergic reactions and results in premature skin aging.
To protect the skin, a number of light-protection filtering substances have therefore 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 Annex 7 of the Cosmetics Directive.
The multiplicity of commercially available sunscreen agents should not, however, distract from the fact that these preparations of the prior art have a range of disadvantages.
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Cosmetic preparations, such as sunscreen preparations, that are applied to the skin regularly come into contact (intentionally or unintentionally) with articles of clothing and laundry articles (e.g., towels) to which they may at times remain stuck (e.g., as “wear”, or because they are absorbed by the fibrous materials). This results in stains and discolorations, depending on the type of ingredients, in particular, on lightly-colored textiles. These discolorations are brought about, in particular, by non-water-soluble UVA and broad-spectrum filters such as 4-(tert.-butyl)4’-methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoylmethane), (2-[-4-(diethylamino)-2hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine). The staining is not readily removed by washing with conventional detergents, and becomes even more intense during the wash cycle due to interactions with ions in the washing water.
More recently, a series of remedies have indeed been developed in order to tackle this textile staining problem by selecting certain ingredients for sunscreen agents. These solutions, however, are disadvantageous in only being effective in emulsion systems but failing with ethanol-based gels and sprays. Because these for the most part transparent sunscreen agents are enjoying growing popularity among consumers, however, the present invention addresses the problem of developing such an ethanolic sunscreen agent that has a reduced tendency to stain textiles. In particular, the problem is to develop an ethanol-based sunscreen agent with reduced textile staining that comprises one or more UV filters selected from the group consisting of the compounds 4-(tert.-butyl)-4’-methoxydibenzoylmethane (INCI Butyl Methoxydibenzoylmethane), (2-[-4-(diethylamino)-2-hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine). The sunscreen agent is therein to have a high sun protection factor, i.e., a sun protection factor of at least 20, preferably at least 30, and especially preferably 50.
It is an object of the present invention to overcome or ameliorate at least one of the disadvantages of the prior art, or to provide a useful alternative.
SUMMARY OF THE INVENTION
According to a first aspect the invention provides an ethanolic cosmetic sunscreen agent comprising:
2017239586 06 Oct 2017
a) one or more UV filters selected from the group consisting of the compounds 4-(tert.-butyl)-4’methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoylmethane), (2-[-4-(diethylamino)-2hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine);
b) ethanol in a minimum quantity of 10 wt%, relative to the total weight of the preparation; and
c) one or more oil components having a contact angle greater than/equal to 44°.
According to a second aspect the invention provides the use of oil components having a contact angle greater than/equal to 44° in ethanolic cosmetic sunscreen agents comprising one or more UV filters selected from the group consisting of the compounds 4-(tert.-butyl)-4’methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoyl-methane), (2-[-4-(diethylamino)-2hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine), in order to make it easier to wash out the UV light protection filters from textiles that have been contaminated with the sunscreen agents.
According to a third aspect the invention provides the use of oil components having a contact angle greater than/equal to 44° in ethanolic cosmetic sunscreen agents comprising one or more UV filters selected from the group consisting of the compounds 4-(tert.-butyl)-4’methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoylmethane), (2-[-4-(diethylamino)-2hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine), in order to reduce the textile staining caused by the sunscreen agent.
According to a fourth aspect the invention provides a method for making it easier to wash out UV filter residues from textiles that have been contaminated with an ethanolic cosmetic sunscreen agent, wherein one or more oil components having a contact angle greater than/equal to 44° is/are added to the ethanolic sunscreen agent, which comprises one or more UV filters selected from the group consisting of the compounds 4-(tert.-butyl)-4’methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoylmethane), (2-[-4-(diethylamino)-2hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine.
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An “ethanolic sunscreen agent” is understood within the scope of the present invention to be a sunscreen agent that comprises at least 10 wt% ethanol relative to the total weight of the preparation. Preferably according to the invention, such an ethanolic sunscreen agent contains from 20 to 75 wt% ethanol and especially preferably from 25 to 70 wt% ethanol, in each case relative to the total weight of the preparation.
Wording such as “according to the invention”, “advantageously according to the invention”, and the like always refer within the scope of the present publication to the sunscreen agent according to the invention, the uses according to the invention, and the method according to the invention, unless otherwise indicated in the particular individual case.
Unless the context clearly requires otherwise, throughout the description and the claims, the words “comprise”, “comprising”, and the like are to be construed in an inclusive sense as opposed to an exclusive or exhaustive sense; that is to say, in the sense of “including, but not limited to”.
DESCRIPTION OF THE INVENTION
The determination of contact angle according to the invention is performed according to the invention by the following method:
Measurement of the contact angle of lipids on glass slides.
The measurements are performed with Dataphysics OCA 20, an optical contact angle meter. The sessile drop technique is used. In this method, a drop of 10 pL of a defined liquid is applied onto a glass slide. The silhouette of the drop formed on the surface is captured with a CCD camera. The image, scanned into a computer, is run through an outline analysis. By creating a baseline and a tangent, the software automatically ascertains the contact angle of the drop on the glass slide. Over a span of 3 seconds, the contact angle is determined with a frame rate of 6.25 fps. The mean contact angle is assessed in each case. To determine the measurement value, five measurements are performed and the result is processed statistically.
It is advantageous according to the invention when one or more compounds from the group consisting of C12-15 alkyl benzoates (INCI: C12-15 Alkyl Benzoate), 2-octyldodecan-1-ol (INCI: Octyldodecanol), and caprylic/capric triglyceride (INCI: Caprylic/Capric Triglyceride) are selected as the oil components having a contact angle greater than/equal to 44°.
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INCI Contact angle (°)
Cyclomethicone 25.84
Dibutyl Adipate 34.72
Butylene Glycol Caprylate/Caprate 40.82
C12-15 Alkyl Benzoate 44.025
Octyldodecanol 52.20
Caprylic/Capric Triglyceride 55.26
Table 1: Contact angle of some oil components used in the cosmetic
It is advantageous according to the invention when the preparation comprises the oil components having a contact angle greater than/equal to 44° in a total concentration of 10 to 70 wt%, relative to the total weight of the preparation. Therein, a total concentration of 15 to 60 wt%, relative to the total weight of the preparation, is preferred according to the invention.
If the preparation according to the invention comprises C12-15 alkyl benzoates (INCI: C12-15 Alkyl Benzoate), then it is advantageous for the purposes of the present invention to use this substance in a concentration of 4 to 15 wt% relative to the total weight of the preparation.
If the preparation according to the invention comprises 2-octyldodecan-1-ol (INCI: Octyldodecanol), then it is advantageous for the purposes of the present invention to use this substance in a concentration of 6 to 25 wt% relative to the total weight of the preparation.
If the preparation according to the invention comprises caprylic/capric triglyceride (INCI: Caprylic/Capric Triglyceride), then it is advantageous for the purposes of the present invention to use this substance in a concentration of 6 to 25 wt% relative to the total weight of the preparation.
It is especially preferred according to the invention when the preparation comprises exclusively oil components that have a contact angle greater than/equal to 44°.
Embodiments of the present invention that are advantageous according to the invention are characterized in that the ethanol content of the preparation is 20 to 75 wt%, relative to the total weight of the preparation.
Embodiments of the present invention that are preferred according to the invention are characterized in that the ethanol content of the preparation is 25 to 70 wt%, relative to the total weight of the preparation.
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It is advantageous for the purposes of the present invention when the total concentration of the UV filters 4-(tert.-butyl)-4’-methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoylmethane), (2-[-4-(diethylamino)-2-hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-([4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine) in the preparation is 0.5 to 15 wt%, relative to the total weight of the preparation. Therein, a total concentration of 1 to 10 wt%, relative to the total weight of the preparation, is preferred according to the invention.
It is advantageous according to the invention when the ethanolic sunscreen agent is transparent. A preparation according to the invention is considered to be transparent, if it is possible, in daylight, to see with the naked eye through a disposable cuvette (company Brand, 2.5 ml_, wavelength range: 220 to 900 nm) filled with the preparation according to the invention. Letters (font type: Arial, size: 8) that are located immediately behind the disposable cuvette have to be clearly recognizable and readable.
According to the invention, it is advantageous when the preparation according to the invention contains no 3-(4-methylbenzylidene)-camphor, 2-hydroxy-4-methoxybenzophenone (INCI: Oxybenzon), phenylen-1,4-bis-(2-benzimidazyl)-3,3’-5,5’-tetrasulfonic acid salts; 1,4-di(2-oxo10-sulfo-3-bornylidene methyl)-benzene and salts thereof; 4-(2-oxo-3-bornylidene methyl) benzenesulfonic acid; 2-methyl-5-(2-oxo-3-bornylidene methyl) sulfonic acid salts, 3benzylidene camphor; terephthalidene dicamphor sulfonic acid; 4-(dimethylamino)-benzoic acid (2-ethylhexyl)ester; di(2-ethylhexyl) 4-methoxybenzalmalonate; isoamyl 4-methoxycinnamoate, and ethylhexyl 4-methoxycinnimate, i.e., is free of these ingredients.
On the other hand, embodiments that are advantageous according to the invention are characterized in that the preparation comprises 2-ethylhexyl 2-hydroxybenzoate (INCI: Ethylhexyl Salicylate) and/or 3,3,5-trimethylcyclohexyl 2-hydroxybenzoate (INCI: Homosalate).
If the preparation comprises 2-ethylhexyl 2-hydroxybenzoate (INCI: Ethylhexyl Salicylate), then, according to the invention, it is advantageous to use this compound in a concentration of 1 to 5 wt%, relative to the total weight of the preparation.
If the preparation comprises 3,3,5-trimethylcyclohexyl 2-hydroxybenzoate (INCI: Homosalate), then, according to the invention, it is advantageous to use this compound in a concentration of 1 to 5 wt%, relative to the total weight of the preparation.
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It may, moreover, be advantageous according to the invention when the preparation according to the invention comprises ethylhexyl-2-cyano-3,3-diphenylacrylate (INCI: Octocrylene).
If the preparation comprises ethylhexyl-2-cyano-3,3-diphenylacrylate (INCI: Octocrylen), then, according to the invention, it is advantageous to use this compound in a concentration of 1 to 10 wt%, relative to the total weight of the preparation.
Also advantageous according to the invention are preparations that do not contain any alkanediols, phenoxyethanol, ethylhexylglycerol, parabens, methylisothiazolinone, chloromethylisothiazolinone, and DMDM hydantoin, i.e., is free of these ingredients.
It is advantageous according to the invention when the preparation according to the invention comprise one or more perfume substances selected from the group consisting of the compounds limonene, citral, linalool, alpha-isomethylionone, geraniol, citronellol, 2-isobutyl-4hydroxy-4-methyltetrahydropyran, 2-tert-pentylcyclohexyl acetate, 3-methyl-5-phenyl-1pentanol, 7-acetyl-1,1,3,4,4,6-hexamethyltetralin, adipic diester, alpha-amylcinnamaldehyde, alpha-methylionone, amyl C butylphenylmethylpropional cinnamal, amyl salicylate, amylcinnamyl alcohol, anise alcohol, benzoin, benzyl alcohol, benzyl benzoate, benzyl cinnamate, benzyl salicylate, bergamot oil, bitter orange oil, butylphenylmethylpropional, cardamom oil, cedrol, cinnamal, cinnamyl alcohol, citronellyl methylcrotonate, citrus oil, coumarin, diethyl succinate, ethyllinalool, eugenol, Evernia furfuracea extract, Evernia prunastri extract, farnesol, guaiacwood oil, hexylcinnamal, hexyl salicylate, hydroxycitronellal, lavender oil, lemon oil, linalyl acetate, mandarin oil, menthyl PCA, methyl heptenone, nutmeg oil, rosemary oil, sweet orange oil, terpineol, tonkabean oil, triethyl citrate, and/or vanillin.
It is moreover advantageous according to the invention when the preparation according to the invention comprises Acrylates/Octylacrylamide Copolymer and/or Vinylpyrrolidone/Hexadecene Copolymer.
If the preparation comprises Acrylates/Octylacrylamide Copolymer, then, according to the invention, it is advantageous to use this compound in a concentration of 0.5 to 5 wt%, relative to the total weight of the preparation.
It is, moreover, especially advantageous for the purposes of the present invention when the preparation according to the invention comprises glycerol.
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A glycerin content of at least 2.0 wt% relative to the total weight of the preparation is especially advantageous according to the invention.
It is especially advantageous according to the invention when the preparation according to the invention comprises less than 3.0 wt% water relative to the total weight of the preparation.
Embodiments of the present invention that are advantageous according to the invention are characterized in that the preparation contains one or more compounds selected from the group consisting of the compounds alpha-lipoic acid, folic acid, phytoene, D-biotin, coenzyme Q10, alpha-glucosylrutin, carnitin, carnosin, glycyrrhetinic acid, natural and/or synthetic isoflavonoids, flavonoids, creatine, creatinine, taurine, β-alanine, panthenol, magnolol, honokiol, tocopheryl acetate, dihydroxyacetone; 8-hexadecene-1,16-dicarboxylic acid, glycerylglycose, (2-hydroxyethyl)urea, vitamin E and/or vitamin E acetate, hyaluronic acid and/or salts thereof, and/or licochalcone A.
The preparation according to the invention may, advantageously according to the invention, exist as a gel, pump spray, or aerosol spray. If the preparation exists as an aerosol spray, then it is especially advantageous according to the invention to use propane, n-butane, isobutane, or mixtures thereof as a propellant gas.
Comparative test
The following testing was able to prove the effect according to the invention, by way of example: In each case, the special oil components were added to a UV filter-containing formulation, and the staining-reducing action (reduction b*) was determined by means of a described method in comparison to a formulation without oil components according to the invention.
Different sunscreen preparations were studied with regard to the formation of yellow spots over one in vitro application/wash cycle. White, pre-washed cotton monitors (100% cotton) were used. 50 mg of the test formulation was evenly distributed onto respective PMMA Schonberg plates (5.0 x 5.0 cm), and directly transmitted onto the test textile by pressing. The stained cotton samples were then air-dried for 12 hours under laboratory conditions.
The drying was followed by colorimetric characterization of the resulting initial staining, through measurement of the degree of yellow with the colorimeter spectro-color (Dr. Lange); colorimetry software: spectral-QC, Version measurement geometry: d/8°, specular component excluded, light type: D65 (corresponding to average daylight), calibration standard: LZM 268, measurement aperture: 10 mm, sample background: without optical brighteners, test climate: 21 °C (±1°C), 41% (±4%) rel. humidity.
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For the evaluation, the change in b-value from the CIE-Lab colorimetry system was used. The b-axis in the CIE-Lab system characterizes the color impression Yellow/Blue, wherein positive b-values stand for an increase in the yellow proportion. The higher the b-value, the greater the yellow impression.
The measurement process was followed by separate washing of the test cloths in the dyeing and washing fastness device Linitest Plus (Atlas) (60°C, 1h, 35rpm, Ariel Compact powder detergent, 10 metal balls as load, VES water with an adjusted water hardness of 14°dH, and an iron ion content of 0.1 mg, and a copper ion content of 0.35 mg/L), and then a rinse cycle (20°C, 2x15 min).
Drying for 12 hours under laboratory conditions was again followed by colorimetric characterization of the resulting staining, through measurement of the color values, as already described, with the colorimeter spectro-color (Dr. Lange).
The CIE lab system or L*a*b* color space is a three-dimensional measurement space that contains all perceptible colors.
The color space is constructed on the basis of the theory of opposite colors. One of the most important properties of the L*a*b* color model is its independence from the instrument, meaning that the colors are defined independently of the way in which they are produced and the reproduction technology.
The corresponding EU directive is DIN EN ISO 11664-4, “Colorimetry - Part 4: CIE 1976 L*a*b* Color space”. The coordinates of the CIELAB plane are formed from the Red/Green value a and the Yellow/Blue value b. The brightness axis L is perpendicular to this plane. According to DIN 6174, L, a, and b are to be written with *, in order to differentiate from other systems, e.g., the Hunter Lab system.
INCI Formula 1 Formula 2 Formula 3 Formula 4 Formula 5
m [%] m [%] m [%] m [%] m [%]
Butyl Methoxydibenzoylmethane 4.50 4.50 4.50 4.50 4.50
Ethylhexyl Salicylate 4.50 4.50 4.50 4.50 4.50
Octocrylene 9.00 9.00 9.00 9.00 9.00
Homosalate 9.00 9.00 9.00 9.00 9.00
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Polysilicone-15 1.00 1.00 1.00 1.00 1.00
Bis-Ethyl hexyloxyphenol Methoxyphenyl Triazine 2.00 2.00 2.00 2.00 2.00
Glycerin 2.50 2.50 2.50 2.50 2.50
Perfume 0.70 0.70 0.70 0.70 0.70
Acrylates/Octylacrylamide Copolymer 1.00 1.00 1.00 1.00 1.00
Di butyl Adipate 3.00
Butylene Glycol Dicaprylate/Dicaprate 3.00
C12-15 Alkyl Benzoate 9.50 15.50 4.00
Octyldodecanol 15.50 5.80
Caprylic/Capric Triglyceride 15.50 5.70
Alcohol Denat. 50.30 50.30 50.30 50.30 50.30
Reduction b* [%] -10.00% -6.10% -5.00% -5.30%
The results show that staining was significantly reduced through the use of complexing agent, in comparison to the formulation without the oil components according to the invention.
2017239586 06 Oct 2017
Examples
The following examples are intended to illustrate, without limiting, the present invention. All quantities, units, and percentages are, unless otherwise indicated, relative to the weight and the total amount or total weight of the preparations.
INCI Example 1 Example 2 Example 3 Example 4
m [%] m [%] m [%] m [%]
Butyl Methoxydibenzoylmethane 4.5 4.5 2.5 2
Ethylhexyl Salicylate 4.5 4.5 2.5 2
Octocrylene 9 9.5 5 4
Homosalate 9 9.5 5 4
Polysilicone-15 1
Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine 2 0.5
Alcohol Denat. 46.8 24.8 24.3 59.3
Glycerin 2.5 5
Perfume 0.7 0.7 0.7 0.7
Acrylates/Octylacrylamide Copolymer + Aqua 1 2 2 1
Caprylic/Capric Triglyceride 7 17 23 8
Octyldodecanol 7 17 23 8
C12-15 Alkyl Benzoate 5 10 12 6
2017239586 06 Oct 2017

Claims (17)

  1. Claims
    1. An ethanolic cosmetic sunscreen agent comprising:
    a) one or more UV filters selected from the group consisting of the compounds 4-(tert.butyl)-4’-methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoylmethane), (2-[-4(diethylamino)-2-hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine);
    b) ethanol in a minimum quantity of 10 wt%, relative to the total weight of the preparation; and
    c) one or more oil components having a contact angle greater than/equal to 44°.
  2. 2. Use of oil components having a contact angle greater than/equal to 44° in ethanolic cosmetic sunscreen agents comprising one or more UV filters selected from the group consisting of the compounds 4-(tert.-butyl)-4’-methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoylmethane), (2-[-4-(diethylamino)-2-hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: BisEthylhexyloxyphenol Methoxyphenyl Triazine), in order to make it easier to wash out the UV light protection filters from textiles that have been contaminated with the sunscreen agent.
  3. 3. Use of oil components having a contact angle greater than/equal to 44° in ethanolic cosmetic sunscreen agents comprising one or more UV filters selected from the group consisting of the compounds 4-(tert.-butyl)-4’-methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoylmethane), (2-[-4-(diethylamino)-2-hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: BisEthylhexyloxyphenol Methoxyphenyl Triazine), in order to reduce the textile staining caused by the sunscreen agent.
  4. 4. A method for making it easier to wash out UV filter residues from textiles that have been contaminated with an ethanolic cosmetic sunscreen agent, wherein one or more oil components having a contact angle greater than/equal to 44° is/are added to the ethanolic sunscreen agent, which contains one or more UV filters selected from the group consisting of the compounds 4-(tert.-butyl)-4’-methoxydibenzoylmethane (INCI: Butyl
    2017239586 06 Oct 2017
    Methoxydibenzoylmethane), (2-[-4-(diethylamino)-2-hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-{[4-(2-ethyl hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: BisEthylhexyloxyphenol Methoxyphenyl Triazine.
  5. 5. The sunscreen agent, method, or use according to any one of the preceding claims, wherein one or more compounds from the group consisting of C12-15 alkyl benzoates (INCI: C12-15 Alkyl Benzoate), 2-octyldodecan-1-ol (INCI: Octyldodecanol), and caprylic/capric triglyceride (INCI: Caprylic/Capric Triglyceride) is selected as the oil components having a contact angle greater than/equal to 44°.
  6. 6. The sunscreen agent, method, or use according to any one of the preceding claims, wherein the preparation comprises the oil components having a contact angle greater than/equal to 44° in a total concentration of 10 to 70 wt%, relative to the total weight of the preparation.
  7. 7. The sunscreen agent, method, or use according to any one of the preceding claims, wherein the ethanol content of the preparation is from 20 to 75 wt% relative to the total weight of the preparation.
  8. 8. The sunscreen agent, method, or use according to any one of the preceding claims, wherein the total concentration of the UV filters 4-(tert.-butyl)-4’methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoylmethane), (2-[-4(diethylamino)-2-hydroxybenzoyl] benzoic acid hexylester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), and 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine) in the preparation is 0.5 to 15 wt%, relative to the total weight of the preparation
  9. 9. The sunscreen agent, method, or use according to any one of the preceding claims, wherein the ethanolic sunscreen agent is transparent.
  10. 10. The sunscreen agent, method, or use according to any one of the preceding claims, wherein the preparation contains no 3-(4-methylbenzylidene)-camphor, 2-hydroxy-4methoxybenzophenone (INCI: Oxybenzon), phenylen-1,4-bis-(2-benzimidazyl)-3,3’-5,5’tetrasulfonic acid salts; 1,4-di(2-oxo-10-sulfo-3-bornylidene methyl)-benzene and salts thereof; 4-(2-oxo-3-bornylidene methyl) benzenesulfonic acid; 2-methyl-5-(2-oxo-3bornylidene methyl) sulfonic acid salts, 3-benzylidene camphor; terephthalidene
    2017239586 06 Oct 2017 dicamphor sulfonic acid; 4-(dimethylamino)-benzoic acid (2-ethylhexyl)ester; di(2ethylhexyl) 4-methoxybenzalmalonate; isoamyl 4-methoxycinnamoate, and ethylhexyl 4methoxycinnimate, i.e., is free of these ingredients.
  11. 11. The sunscreen agent, method, or use according to any one of the preceding claims, wherein the preparation contains 2-ethylhexyl 2-hydroxybenzoate (INCI: Ethylhexyl Salicylate) and/or 3,3,5-trimethylcyclohexyl 2-hydroxybenzoate (INCI: Homosalate).
  12. 12. The sunscreen agent, method, or use according to any one of the preceding claims, wherein the preparation comprises ethylhexyl-2-cyano-3,3-diphenylacrylate (INCI: Octocrylen).
  13. 13. The sunscreen agent, method, or use according to any one of the preceding claims, wherein the preparation does not contain any alkanediols, phenoxyethanol, ethylhexylglycerol, parabens, methylisothiazolinone, chloromethylisothiazolinone, and DMDM hydantoin, i.e., is free of these ingredients.
  14. 14. The sunscreen agent, method, or use according to any one of the preceding claims, wherein the preparation comprises one or more perfume substances selected from the group consisting of the compounds limonene, citral, linalool, alpha-isomethylionone, geraniol, citronellol, 2-isobutyl-4-hydroxy-4-methyltetrahydropyran, 2-tert-pentylcyclohexyl acetate, 3-methyl-5-phenyl-1 -pentanol, 7-acetyl-1,1,3,4,4,6-hexamethyltetralin, adipic diester, alpha-amylcinnamaldehyde, alpha-methylionone, amyl C butylphenylmethylpropional cinnamal, amyl salicylate, amylcinnamyl alcohol, anise alcohol, benzoin, benzyl alcohol, benzyl benzoate, benzyl cinnamate, benzyl salicylate, bergamot oil, bitter orange oil, butylphenylmethylpropional, cardamom oil, cedrol, cinnamal, cinnamyl alcohol, citronellyl methylcrotonate, citrus oil, coumarin, diethyl succinate, ethyllinalool, eugenol, Evernia furfuracea extract, Evernia prunastri extract, farnesol, guaiacwood oil, hexylcinnamal, hexyl salicylate, hydroxycitronellal, lavender oil, lemon oil, linalyl acetate, mandarin oil, menthyl PCA, methyl heptenone, nutmeg oil, rosemary oil, sweet orange oil, terpineol, tonkabean oil, triethyl citrate, and/or vanillin.
  15. 15. The sunscreen agent, method, or use according to any one of the preceding claims, wherein the preparation comprises Acrylates/Octylacrylamide Copolymer.
    2017239586 06 Oct 2017
  16. 16. The sunscreen agent, method, or use according to any one of the preceding claims, wherein the preparation comprises less than 3.0 wt% water, relative to the total weight of the preparation.
  17. 17. The sunscreen agent, method, or use according to any one of the preceding claims, wherein the preparation comprises exclusively oil components that have a contact angle greater than/equal to 44°.
AU2017239586A 2016-10-20 2017-10-06 Ethanolic sunscreen agent with reduced tendency to stain textiles Abandoned AU2017239586A1 (en)

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DE102016220547.1A DE102016220547A1 (en) 2016-10-20 2016-10-20 Ethanolic sunscreen with reduced tendency to textile staining
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DE102016220547A1 (en) 2016-10-20 2018-04-26 Beiersdorf Ag Ethanolic sunscreen with reduced tendency to textile staining
BR112020023309B1 (en) * 2018-05-18 2023-12-26 Dsm Ip Assets B.V. TOPIC COMPOSITION
DE102018216823A1 (en) * 2018-10-01 2020-04-02 Beiersdorf Ag Fatty alcohol-containing, ethanolic sunscreen with a reduced tendency to stain textiles
DE102020204937A1 (en) * 2020-04-20 2021-10-21 Beiersdorf Aktiengesellschaft Environmentally friendly sunscreen
DE102020204938A1 (en) * 2020-04-20 2021-10-21 Beiersdorf Aktiengesellschaft Environmentally friendly cosmetic sunscreen

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DE102005059742A1 (en) 2005-12-13 2007-06-14 Beiersdorf Ag Transparent sunscreen
DE102006029837A1 (en) * 2006-06-27 2008-01-03 Henkel Kgaa Detergent or treatment agent portion II
DE102008018788A1 (en) 2008-04-11 2009-10-15 Beiersdorf Ag Perfumed cosmetic preparation
ES2681207T3 (en) * 2009-07-07 2018-09-12 Basf Se UV filter combinations comprising benzylidene malonate
JP2013513570A (en) * 2009-12-09 2013-04-22 ディーエスエム アイピー アセッツ ビー．ブイ． New compounds
DE102010008320A1 (en) 2010-02-17 2011-08-18 Beiersdorf AG, 20253 Use of substances to improve the washability of textile stains caused by UV filters
DE102010050774A1 (en) * 2010-11-10 2012-05-10 Beiersdorf Ag Cosmetic sunscreen spray
WO2012168285A2 (en) * 2011-06-08 2012-12-13 Dsm Ip Assets B.V. Sunscreens
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DE102013203022A1 (en) 2013-02-25 2014-08-28 Beiersdorf Ag Sunscreen with dialkyl esters for use on wet skin
DE102014201541A1 (en) * 2014-01-29 2015-07-30 Beiersdorf Ag Octocrylene-free sunscreen with low tack
DE102014207924A1 (en) * 2014-04-28 2015-10-29 Beiersdorf Ag Sunscreens with reduced tendency to textile staining IV
DE102014207916A1 (en) * 2014-04-28 2015-10-29 Beiersdorf Aktiengesellschaft Sunscreen with reduced tendency to textile staining II
DE102014207919A1 (en) * 2014-04-28 2015-10-29 Beiersdorf Ag Sunscreen with reduced tendency to textile staining I
DE102014207935A1 (en) * 2014-04-28 2015-10-29 Beiersdorf Ag Sunscreen with reduced tendency to textile staining III
ES2819207T3 (en) * 2014-04-29 2021-04-15 Symrise Ag Active mixes
DE102015214499A1 (en) 2015-07-30 2017-02-02 Beiersdorf Aktiengesellschaft Odor-stable octocrylene-containing preparation
DE102016211238A1 (en) 2016-06-23 2017-12-28 Beiersdorf Ag Sunscreen with reduced textile stain
DE102016220547A1 (en) 2016-10-20 2018-04-26 Beiersdorf Ag Ethanolic sunscreen with reduced tendency to textile staining

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CN107961169A (en) 2018-04-27
EP3311791A1 (en) 2018-04-25
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EP3311791B1 (en) 2020-06-17
ES2817575T3 (en) 2021-04-07

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