AU2017202205A1

AU2017202205A1 - Novel sunscreen with a reduced tendency to discoloration of textiles

Info

Publication number: AU2017202205A1
Application number: AU2017202205A
Authority: AU
Inventors: Dominik Goddertz; Anja Pasternak; Sarah Sprock
Original assignee: Beiersdorf AG
Current assignee: Beiersdorf AG
Priority date: 2016-04-05
Filing date: 2017-04-04
Publication date: 2017-10-19
Also published as: EP3228299A1; BR102017006742A2; EP3228299B1; DE102016205580A1; CN107320349A

Abstract

Abstract Method and applications for improving the washability of cosmetic preparations containing UV filters out of textiles, wherein 4-hydroxyacetophenone is added to the cosmetic.

Description

Novel Sunscreen with a Reduced Tendency to Discoloration of Textiles

The present invention relates to methods and applications for facilitating the washability of UV protectant filter-containing cosmetic preparations from textiles, characterized in that the cosmetic 4-hydroxyacetophenone is added.

The trend away from preferring pale skin to "healthy athletically tanned skin" has been uninterrupted for many years. To achieve this goal, people exposed their skin to solar radiation because it causes the formation of a pigment in the sense of formation of melamine. However, the ultraviolet radiation of sunlight also has a damaging effect on skin. In addition to acute damage (sunburn), long-term damage also occurs such as an increased risk of developing skin cancer in a case of excessive exposure to light of the UVB range (wavelength 230-320 nm). The excessive influence of UVB and UVA radiation (wavelength 320-400 nm) also results in weakening of the elastic and collagen fibers of the connective tissue, which in turn results in numerous phototoxic and photoallergic reactions and causes premature aging of skin.

Therefore, a number of sun protection filter substances that can be used in cosmetic preparations have been developed. In most industrial countries, these UVA- and UVB filters have been combined in the form of positive lists, such as Addendum 7 to the German Cosmetic Regulations.

However, the multitude of commercially available sunscreens must not conceal the fact that these state-of-the-art preparations have a number of disadvantages.

Cosmetic preparations such as sunscreen preparations that are applied to skin frequently (whether intentionally or unintentionally) come in contact with clothing items and laundry items (e.g., hand towels), to which they partially adhere (e.g., as "abrasion" or because they are "absorbed" by the fibers). This results in spots and discoloration, depending on the type of ingredients, in particular on light textiles. This discoloration is caused in particular by non-water-soluble UVA filters and broad-band filters. The spots are difficult to remove by washing with the traditional detergents and they may even be intensified during the laundry process due to interactions with ions in the wash water.

An object of an embodiment of present invention was therefore to eliminate the disadvantages of the prior art and to find ways for being able to more easily wash a cosmetic preparation (in particular a sunscreen) containing non-water-soluble UVA filters and/or broad-band filters out of the textiles contaminated with the preparation more easily.

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.

An object is surprisingly achieved by a method for facilitating the washability of cosmetic preparations containing UV filters from textiles, and is characterized in that 4-hydroxyacetophenone is added to the cosmetic.

An object is surprisingly achieved by a method for reducing the textile spotting caused by cosmetic preparations containing UV filters, and is characterized in that 4-hydroxyacetophenone is added to the cosmetic.

An object is surprisingly achieved by using 4-hydroxyacetophenone in cosmetic preparations containing UV filters to facilitate the washability of the UV filters out of textiles contaminated with these preparations.

An object is surprisingly achieved by using 4-hydroxyacetonone in cosmetic preparations containing UV filters to reduce the textile spotting caused by the preparations.

Any discussion of the prior art throughout the specification should in no way be considered as an admission that such prior art is widely known or forms part of common general knowledge in the field.

Those skilled in the art are surely familiar with WO 2011/101250, DE 10 2014 104255, DE 10 2014 104256 as well as EP 2939710, i.e., sunscreens containing 4-hydroxyacetophenone were basically familiar to those skilled in the art. Nevertheless, these publications did not point to the present invention because the effect of 4-hydroxyacetophenone on washability was not recognized. This effect was even more surprising because 4-hydroxyacetophenone per se is not particularly readily soluble in water. 4-Hydroxyacetophenone, which is also known as p-hydroxyacetophenone or 1 -(4-hydroxyphenyl)ethane (INCI: hydroxyacetophenone) can be obtained from the Symrise Co. under the brand name Symsave H, for example.

When used within the scope of the present invention, the terms "inventive preparation," "inventive" and "according to the invention," etc. always refer to the method and the application according to the invention.

The terms cosmetic preparation and cosmetic are used synonymously.

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”.

The terms comprising and containing are used synonymously.

In accordance with a first aspect of the present invention there is provided a method for improving the washability of cosmetic preparations comprising UV filters out of textiles, wherein 4-hydroxyacetophenone is added to the cosmetic.

In accordance with a second aspect of the present invention there is provided a method for reducing the textile spotting caused by cosmetic preparations comprising UV filters, wherein 4-hydroxyacetophenone is added to the cosmetic.

In accordance with a third aspect of the present invention there is provided use of 4-hydroxyacetophenone in cosmetic preparations comprising UV filters to improve the washability of the UV filters out of textiles contaminated with these preparations.

In accordance with a fourth aspect of the present invention there is provided use of 4-hydroxyacetophenone in cosmetic preparations comprising 4-hydroxyacetophenone in UV filters to reduce the textile spotting caused by the preparation.

The cosmetic preparation, i.e., the cosmetic, of the method and applications according to embodiments of the invention advantageously contains the compounds 4-(tert-butyl)-4'-methoxydibenzoylmethane (INCI: butyl methoxydibenzoylmethane) and/or 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: bis-ethylhexyloxyphenol methoxyphenyl triazine).

Three variants according to embodiments of the invention are described as follows:

If the cosmetic preparation contains 4-(tert-butyl)-4'-methoxydibenzoylmethane (INCI: butyl methoxydibenzoylmethane) but does not contain bis-ethylhexyloxyphenol methoxyphenyl triazine, then it is advantageous according to the invention if the amount of 4-(tert-butyl)-4'-methoxydibenzoylmethane (INCI: butyl methoxydibenzoylmethane) amounts to 0.1 to 5% by weight, based on the total weight of the preparation.

If the cosmetic preparation contains 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: bis-ethylhexyloxyphenol methoxyphenyl triazine) and does not contain any butyl methoxydibenzoylmethane, then it is advantageous according to the invention if the amount of 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: bis-ethylhexyloxyphenol methoxyphenyl triazine) amounts to 0.1 to 10% by weight, based on the total weight of the preparation.

If the cosmetic preparation contains 4-(tert-butyl)-4'-methoxydibenzoylmethane (INCI: butyl methoxydibenzoylmethane) and 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(4-methoxy-phenyl)-1,3,5-triazine (INCI: bis-ethylhexyloxyphenol methoxyphenyl triazine), then it is advantageous according to the invention if the amount of 4-(tert-butyl)-4'-methoxydibenzoyl-methane (INCI: butyl methoxydibenzoylmethane) is from 0.1 to 5% by weight and the amount of 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: bis-ethylhexyloxyphenol methoxyphenyl triazine) is from 0.1 to 10% by weight, each based on the total weight of the preparation.

It is advantageous for the inventive method and the inventive application according to the invention if the cosmetic preparation, i.e., the cosmetic comprises from 0.01 to 2% by weight 4-hydroxyacetophenone, based on the total weight of the preparation.

It is preferred according to the invention for the inventive method and the inventive application if the cosmetic preparation, i.e., the cosmetic comprises from 0.1 to 1% by weight 4-hydroxyacetophenone, based on the total weight of the preparation.

In addition, the cosmetic preparation may advantageously also comprise additional UV filters which are selected for example from the group of compounds 2-phenylbenzimidazole-5-sulfonic acid and/or the salts thereof; phenylene-1,4-bis-(2-benzimidazyl)-3,3'-5,5'-tetrasulfonic acid salts; 1,4-di(2-oxo-10-sulfo-3-bornylidenemethyl)benzene and salts thereof; 4-(2-oxo-3-bornylidenemethyl)benzene sulfonic 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-benzylidene camphor; ethylhexyl salicylate; terephthalidene dicamphor sulfonic acid; 2-ethylhexyl-2-cyano-3,3-diphenylacrylate; 4-(dimethylamino)benzoic acid (2-ethylhexyl) ester; 4-(dimethylamino)benzoic acid amyl ester; 4-methoxybenzalmalonic acid di(2-ethylhexyl) ester; 4-methoxycinnamic acid isoamyl ester; 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone; 2,2'-dihydroxy-4-methoxybenzophenone; 2-(4'-diethylamino-2'-hydoxybenzoyl)benzoic acid hexyl ester; homomenthyl salicylate; 2-ethylhexyl-2-hydroxybenzoate; dimethicodiethylbenzal malonate; 3-(4-(2,2-bis-ethoxycarbonylvinyl)-phenoxy)propenyl)methoxysiloxane/dimethylsiloxane copolymer; dioctylbutylamidotriazone (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); 2,4,6-tribiphenyl-4-yl-1,3,5-triazine; merocyanine; piperazine derivate; titanium dioxide; zinc oxide.

It is advantageous according to the invention if the inventive preparation is free of 2-ethylhexyl-2-cyano-3,3-diphenylacrylate, 2-hydroxy-4-methoxybenzophenone and/or 3-(4-methyl-benzylidene)camphor. It is preferable to refrain from using 3-(4-methylbenzylidene)camphor and/or 2-hydroxy-4-methoxybenzophenone.

The effect according to the invention can be improved according to the invention by adding one or more chelating agents to the cosmetic.

It is preferred according to the invention if one or more of the compounds from the following group and/or their alkali salts are used:

- 1 -hydroxyethane-(1,1 -diphosphonic acid) - HEDP

- aminotrimethylene phosphonic acid - ATMP

- diethylenetriaminepenta(methylene phosphonic acid) - DTPMP

- ethylenediaminetetra(methylene phosphonic acid - EDTMP

- phosphonobutane tricarboxylic acid - PBTC

- iminodisuccinate - IDS - sodium polyphosphate - tetrasodium pyrophosphate - hydroxamic acid - polygalacturonic acid - succinic acid - formic acid - malic acid - ethylenediamine tetraacetic acid - EDTA.

It is especially preferred according to the invention if one or more of the compounds from the following group and/or their alkali salts and/or their amine N-oxides are used:

- diethylenetriaminepenta(methylene phosphonic acid) - DTPMP

- ethylenediaminetetra(methylene phosphonic acid) - EDTMP

- aminotrimethylene phosphonic acid - ATMP

- phosphonobutane tricarboxylic acid - PBTC

- iminodisuccinate - IDS - sodium polyphosphate - tetrasodium pyrophosphate - succinic acid.

The total use concentration of the chelating agents (one or more) preferred according to the invention amounts to 0.01 to 3% by weight, based on the total weight of the preparation.

The effect according to the invention can be improved according to the invention by adding to the cosmetic 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1 H)-pyridone (piroctone) and/or the monoethanolamine salt thereof.

The total use concentration for piroctone preferred according to the invention amounts to 0.01 to 1% by weight, based on the total weight of the preparation.

The effect according to the invention can be improved according to the invention by adding siloxane elastomers to the cosmetic.

The total use concentration for siloxane elastomers (one or more) that are preferred according to the invention amounts to 0.1 to 20% by weight, based on the total weight of the preparation.

Not least of all, the inventive effect can be improved according to the invention by adding one or more polysaccharides to the cosmetic.

The polysaccharides according to the invention may be selected from various substance groups.

Thus, in an advantageous embodiment of the present invention, the polysaccharides that are used are selected from the group of gums.

In such a case, it is preferable according to the invention if the polysaccharides that are used are selected from the group of compounds welan gum, sclerotium gum and cellulose gum.

However, the advantageous polysaccharides according to this invention may also be selected from the group of compounds alginates (sodium alginate in particular) and carboxymethylcellulose.

In any case, it is advantageous according to the invention if the preparation comprises polysaccharides in a total amount of 0.01 to 2% by weight, based on the total weight of the preparation.

For the individual substances, the following use concentrations are considered to be preferred according to the invention for the advantageous polysaccharides according to the invention:

Welan gum is preferably used according to the invention in a concentration of 0.01 to 1.5% by weight, based on the total weight of the composition. The raw material Collstab W-100 from the Colltec Co. may advantageously be used as the welan gum.

Sclerotium gum is preferably used according to the invention in a concentration of 0.01 to 1.5% by weight, based on the total weight of the composition. The raw material Actigum CS 11 from the Cargill Co., for example, may advantageously be used as the sclerotium gum.

Cellulose gum is preferably used according to the invention in a concentration of 0.01 to 1.5% by weight, based on the total weight of the composition. The raw material Blanose cellulose gum from the Ashland Co., for example, may be used advantageously as the cellulose gum.

Sodium alginate is preferably used according to the invention in a concentration of 0.01 to 1.5% by weight, based on the total weight of the composition. The raw material alginic acid sodium salt from the Sigma Aldrich Co., for example, may be used advantageously as the sodium alginate.

Carboxymethylcellulose is preferably used according to the invention in a concentration of 0.01 to 2% by weight, based on the total weight of the composition. The raw material Aqualon CMC from the Ashland Co., for example, may be used advantageously as the carboxymethylcellulose.

In advantageous embodiments of the present invention, the preparation is present in the form of an oil-in-water emulsion (O/W emulsion).

In such a case, the preferred embodiments comprise one or more emulsifiers, selected from the group of compounds glycerylstearate citrate, cetearyl alcohol sodium cetearyl sulfate + glyceryl stearate, cetearyl sulfosuccinate sodium stearoyl glutamate, polyglyceryl-3-methylglucose distearate, stearic acid, potassium cetyl phosphate.

In addition, the cosmetic preparation may be formulated like a conventional cosmetic for such cases and may contain the corresponding known ingredients.

Comparative experiment/Exemplary embodiment

Washing experiment of the following formulas with the LINI test:

Formula A (O/W sunscreen lotion SPF 30 without hydroxyacetophenone)

Formula B (formula A + 0.6% hydroxyacetophenone)

Formula C (O/W sunscreen lotion SPF 50+ without hydroxyacetophenone)

Formula D (formula C = 1% hydroxyacetophenone)

All formulas contain the compounds 4-(tert-butyl)-4'-methoxydibenzoylmethane (INCI: butyl methoxydibenzoylmethane) and 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(4-methoxy-phenyl)-1,3,5-triazine (INCI: bis-ethylhexyloxyphenol methoxyphenyl triazine).

Spot monitor:

Dry prewashed cotton cloths 1) With the help of PMMA plates, the test formulas are applied to the spot monitors (2 mg/cm2). Four spots are created per formula. The spots are left to dry overnight. 2) With the help of a spectro pen (Dr. Lange spectro-pen), the I*-, a*- and b* values of the unspotted cotton cloth as well as those of the dried spots are recorded (10 measurement points per spot). 3) The spots are washed in a LINI test using steel balls as an added load (60 min. at 60°C). The wash water contains 3.33 g all-purpose detergent powder/L. Then the cloths are rinsed for 15 minutes while storing in tap water. 4) After they had dried overnight, the I*-, a*- and b*- values are measured as described under 1) and the spotting (in particular the b* value) before and/or after the washing process is calculated.

This yields the results shown in Figure 1 for the tested formulas:

The yellow values for the textile prepared with sunscreen are shown before washing at the left of the figure and after washing at the right of the figure.

Conclusion: It was found that the UV filters 4-(tert-butyl)-4'-methoxydibenzoylmethane (INCI: butyl methoxydibenzoylmethane) and 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: bis-ethylhexyloxyphenol methoxyphenyltriazine) can be washed out of the cotton fabric more easily and more thoroughly, and the textile spotting caused by these UV filters can be reduced significantly.

Examples of recipes/sunscreens with which the method and the application according to the invention can be carried out:

All quantities, amounts and percentages are based on weight and the total amount and/or total weight of the preparations, unless otherwise indicated. 1) O/W sunscreen lotion_wt%

Cetyl alcohol 1.0

Glyceryl stearate citrate 2.0 C12-15 alkyl benzoate 6.0

Stearyl alcohol 0.5

Homosalate 8.5

Octocrylene 9.0

Ethylhexyl salicylate 3.5

Butyl methoxydibenzoylmethane 4.0

Myristyl myristate 1.0

Hydrogenated cocoglycerides 1.0 VP/hexadecene copolymer 0.5

Tocopheryl acetate 0.2

Titanium dioxide (nano) 3.0

Sodium Carboxymethylcellulose 0.1

Acrylates/C 10-30 alkyl acrylate crosspolymer 0.1

Xanthan gum 0.3

Trisodium EDTA 0.7

Glycerin 5.0

Tetrasodium iminodisuccinate 0.5

Sodium hydroxide q.s.

Denatured alcohol 4.0

Hydroxyacetophenone 0.5

Panthenol 1.0

Perfume 0.4

Ethylhexyl glycerin 0.3

Water add to 100 2) 0/W sunscreen lotion_wt%

Sodium carboxymethylcellulose 0.5

Tocopheryl acetate 0.06

Hydroxyacetophenone 0.6

Ethylhexyl glycerin 0.5 C12-15 alkyl benzoate 3.0

Butylene glycol dicaprylate/dicaprate 1.0 018-38 alkyl hydroxystearoyl stearate 1.5

Glyceryl stearate 1.0

Sodium stearoyl glutamate 0.3

Silica dimethyl silylate 0.5

Triacontanyl PVP 1.0

Glycerin 2.0

Sodium hydroxide q.s. (pH 7.3)

Stearyl alcohol 1.0

Acrylates/Cio-30 alkyl acrylate crosspolymer 0.15

Xanthan gum 0.4

Denatured alcohol 5.0

Trisodium EDTA 0.8

Tetrasodium iminodisuccinate 0.75

Homosalate 8.5

Ethylhexyl salicylate 4.5

Bis-ethylhexyloxyphenol methoxyphenyl triazine 2.0

Ethylhexyl triazone 1.0

Butyl methoxydibenzoylmethane 3.5

Phenylbenzimidazole sulfonic acid 1.0

Water add to 100 3) O/W sunscreen spray_wt%

Tocopheryl acetate 0.1

Hydroxyacetophenone 0.4

Panthenol 1.4

Copernicia cerifera cera 0.5

Glyceryl stearate 1.0

Sodium stearoyl glutamate 0.4 VP/hexadecene copolymer 0.5

Glycerin 4.0

Citric acid q.s. (pH 7.3)

Phenoxyethanol 0.5

Sodium carboxymethylcellulose 0.5

Xanthan gum 0.1

Microcrystalline cellulose + cellulose gum 0.9

Denatured alcohol 4.0

Trisodium EDTA 0.7

Tetrasodium iminodisuccinate 0.8

Homosalate 8.5

Octocrylene 5.0

Ethylhexyl salicylate 4.5

Butyl methoxydibenzoylmethane 3.0

Phenylbenzimidazole sulfonic acid 0.5

Water add to 100

Claims

Patent Claims

1. A method for improving the washability of cosmetic preparations comprising UV filters out of textiles, wherein 4-hydroxyacetophenone is added to the cosmetic.
2. A method for reducing the textile spotting caused by cosmetic preparations comprising UV filters, wherein 4-hydroxyacetophenone is added to the cosmetic.
3. Use of 4-hydroxyacetophenone in cosmetic preparations comprising UV filters to improve the washability of the UV filters out of textiles contaminated with these preparations.
4. Use of 4-hydroxyacetophenone in cosmetic preparations comprising 4-hydroxyacetophenone in UV filters to reduce the textile spotting caused by the preparation.
5. The method or use according to any one of the preceding claims, wherein the cosmetic preparation, i.e., the cosmetic, comprises the compounds 4-(tert-butyl)-4'-methoxydibenzoylmethane (INCI: butyl methoxydibenzoylmethane) and/or 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: bis-ethylhexyloxyphenol methoxyphenyl triazine).
6. The method or use according to any one of the preceding claims, wherein the cosmetic preparation and/or the cosmetic comprises 0.01 to 2% by weight 4-hydroxyacetophenone, based on the total weight of the preparation.
7. The method or use according to any one of the preceding claims, wherein the preparation comprises one or more chelating agents selected from the group - 1-hydroxyethane-(1,1-diphosphonic acid) - HEDP - aminotrimethylene phosphonic acid - ATMP - diethylenetriaminepenta(methylene phosphonic acid) - DTPMP - ethylenediaminetetra(methylene phosphonic acid - EDTMP - phosphonobutane tricarboxylic acid - PBTC - iminodisuccinate - IDS - sodium polyphosphate - tetrasodium pyrophosphate - hydroxamic acid - polygalacturonic acid - succinic acid - formic acid - malic acid - ethylenediamine tetraacetic acid - EDTA and/or the alkali salts thereof.
8. The method or use according to any one of the preceding claims, wherein the cosmetic comprises 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1 H)-pyridone (piroctone) and/or the monoethanolamine salt thereof.
9. The method or use according to any one of the preceding claims, wherein siloxane elastomer is added to the cosmetic.
10. The method or use according to any one of the preceding claims, wherein polysaccharide is added to the cosmetic.