Novel cosmetic preparation containing vanillin and ethylhexyloxyphenol methoxyphenyl triazine

A cosmetic preparation with Vanillin, Bis-Ethylhexyloxyphenol methoxyphenyl Triazine, dipropylene glycol dibenzoate, and benzyl benzoate addresses crystallization issues, ensuring UV protection and sensory quality in cosmetic formulations.

WO2025223885A1PCT designated stage Publication Date: 2025-10-30BEIERSDORF AG
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Patent Information

Application Number
PCT/EP2025/060045
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-04-23
Filing Date
2025-04-11
Publication Date
2025-10-30

AI Technical Summary

Technical Problem

The crystallization of vanillin and other lipophilic compounds is triggered by the UV light protection filter Bis-Ethylhexyloxyphenol methoxyphenyl Triazine, leading to reduced sensory properties and UV protection in cosmetic preparations.

Method used

A cosmetic preparation combining 4-hydroxy-3-methoxybenzaldehyde (Vanillin), Bis-Ethylhexyloxyphenol methoxyphenyl Triazine, dipropylene glycol dibenzoate, and benzyl benzoate, with specific concentration ranges, prevents crystallization and maintains UV protection.

Benefits of technology

The solution effectively prevents crystallization of vanillin and maintains UV protection in cosmetic preparations, even under light exposure, enhancing sensory properties and efficacy.

✦ Generated by Eureka AI based on patent content.

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Abstract

A cosmetic preparation containing 4-Hydroxy-3-methoxybenzaldehyde (INCI: vanillin), 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: bis-ethylhexyloxyphenol methoxyphenyl triazine), dipropylene glycol dibenzoate (INCI: dipropylene glycol dibenzoate) and benzyl benzoate (INCI: benzyl benzoate).
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Description

[0001] New cosmetic preparation with vanillin and ethylhexyloxyphenol methoxyphenyl triazine

[0002] The present invention relates to a cosmetic preparation containing 4-hydroxy-3-methoxybenzaldehyde (INCI: Vanillin), 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol methoxyphenyl Triazine), dipropylene glycol dibenzoate (INCI: Dipropylene Glycol Dibenzoate) and benzyl benzoate (INCI: Benzyl Benzoate).

[0003] The desire to look beautiful and attractive is rooted in human nature. Even though the ideal of beauty has changed over time, the pursuit of a flawless appearance has always been a human goal. The condition and appearance of the skin plays a significant role in achieving a beautiful and attractive appearance.

[0004] For the skin to fully perform its biological functions, it requires regular cleansing and care. Cleansing the skin removes dirt, sweat, and dead skin cells, which provide an ideal breeding ground for pathogens and parasites of all kinds. Skin care products primarily moisturize and replenish the skin's natural oils. They often contain active ingredients that regenerate the skin or protect it from the harmful effects of UV radiation.

[0005] Cosmetics usually contain a number of perfumes intended to mask unpleasant inherent odors of preparation ingredients and to give the cosmetic its individual, manufacturer-typical scent.

[0006] However, a disadvantage of the state of the art is that the perfume ingredient vanillin (4-hydroxy-3-methoxybenzaldehyde) tends to crystallize out of the cosmetic preparations in the presence of the UV light protection filter 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol methoxyphenyl Triazine). These crystallization nuclei then in turn lead to the crystallization of other poorly soluble, lipophilic compounds, in particular the 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis- Ethylhexyloxyphenol methoxyphenyl Triazine), so that not only do the sensory properties of the preparation suffer from the crystal formation, but also the UV protection (especially the UV protection) of the affected cosmetic preparation is reduced or completely lost.

[0007] To suppress crystallization phenomena of lipophilic UV sunscreens, the oil component C12-15 alkyl benzoate is commonly used, a compound that is particularly suitable for keeping 2,4-Bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1 ,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol methoxyphenyl Triazine) in solution in the oil phase.

[0008] A disadvantage of the prior art, however, is that vanillin precipitates particularly quickly and thoroughly from the preparation in C12-15 alkyl benzoate. Therefore, in the combination of 4-hydroxy-3-methoxybenzaldehyde (INCI: vanillin), 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: bis-ethylhexyloxyphenol methoxyphenyl triazine), and C12-15 alkyl benzoate (especially under the influence of light), increased crystal formation occurs, which is precisely what should be prevented.

[0009] The object of the present invention was therefore to develop a combination of substances for cosmetic sunscreens that can be perfumed with vanillin without having to forgo (or use in a significantly reduced amount) the widely used UV filter 2,4-Bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4- methoxyphenyl)-1 ,3,5-triazine (INCI: Bis- Ethylhexyloxyphenol methoxyphenyl Triazine).

[0010] The problem is surprisingly solved by a cosmetic preparation containing 4-hydroxy-3-methoxybenzaldehyde (INCI: Vanillin), 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis- Ethylhexyloxyphenol methoxyphenyl Triazine), dipropylene glycol dibenzoate (INCI: Dipropylene Glycol Dibenzoate) and benzyl benzoate (INCI: Benzyl Benzoate).

[0011] According to the invention, it is advantageous if the preparation contains 4-hydroxy-3-methoxybenzaldehyde (INCI: Vanillin) in a concentration of 0.0002 to 1.5 wt%, based on the total weight of the preparation. The preferred concentration according to the invention is between 0.004 and 0.5 wt%, based on the total weight of the preparation. Advantageous embodiments of the present invention are characterized in that the preparation contains 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol methoxyphenyl Triazine) in a concentration of 0.5 to 9.5 wt%, based on the total weight of the preparation. The preferred concentration according to the invention is between 0.5 and 5.0 wt%, based on the total weight of the preparation.

[0012] According to the invention, it is advantageous if the preparation contains dipropylene glycol dibenzoate (INCI: Dipropylene Glycol Dibenzoate) in a concentration of 0.5 to 10% by weight, based on the total weight of the preparation. The preferred concentration according to the invention is between 1.0 and 5.0% by weight, based on the total weight of the preparation.

[0013] Furthermore, according to the invention, it is advantageous if the preparation contains benzyl benzoate (INCI: Benzyl Benzoate) in a concentration of 0.0001 to 0.1 wt%, based on the total weight of the preparation. The preferred concentration according to the invention is between 0.0002 and 0.02 wt%, based on the total weight of the preparation.

[0014] Advantageous embodiments of the present invention are further characterized in that the preparation contains Ci2-is-alkylbenzoate in a concentration of at most 10 wt%, based on the total weight of the preparation.

[0015] In addition to 2,4-Bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1 ,3,5-triazine (INCI: Bis- Ethylhexyloxyphenol methoxyphenyl Triazine), the preparation according to the invention may contain further UV filters.

[0016] In particular, according to the invention, it is advantageous if the preparation contains (2-[-4-(Diethylamino)-2-hydroxybenzoyl] Benzoic acid hexyl ester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), 2,4,6-Tris-[anilino-(p-carbo-2'-ethyl-T-hexyloxy)]-1,3,5-triazine (INCI: Ethylhexyl Triazone) and / or 4-(tert-Butyl)-4'-methoxydibenzoylmethane (INCI Butyl Methoxydibenzoylmethane).

[0017] If the preparation according to the invention contains 2-[-4-(Diethylamino)-2-hydroxybenzoyl]hexyl benzoate (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), this substance is advantageously used according to the invention in a concentration of 0.5 to 9.5% by weight, based on the total weight of the preparation. If the preparation according to the invention contains 2,4,6-tris-[anilino-(p-carbo-2'-ethyl-1'-hexyloxy)]-1,3,5-triazine (INCI: Ethylhexyl Triazone), this substance is advantageously used according to the invention in a concentration of 0.3 to 5.0% by weight, based on the total weight of the preparation.

[0018] The preparation according to the invention contains 4-(tert-Butyl)-4'-methoxydibenzoylmethane (INCI Butyl Methoxydibenzoylmethane), this substance is advantageously used according to the invention in a concentration of 1.0 to 5.0 wt%, based on the total weight of the preparation.

[0019] Furthermore, it is advantageous in the context of the present invention if the preparation contains ethylhexylglycerin. In such a case, the preparation according to the invention is preferably characterized in that the preparation contains ethylhexylglycerin in a concentration of 0.01 to 0.75% by weight, based on the total weight of the preparation.

[0020] According to the invention, the preparation can be in two different dosage forms: in the form of an ethanolic solution and in the form of an emulsion.

[0021] If the preparation is in the form of an ethanolic solution, the ethanol concentration is advantageously 30 to 55% by weight according to the invention, based on the total weight of the preparation.

[0022] If the preparation is in the form of an emulsion, it is also advantageous according to the invention if the preparation contains ethanol.

[0023] In general, if the emulsion according to the invention contains ethanol, the advantageous embodiments according to the invention are characterized in that the preparation optionally contains ethanol in a concentration of 3 to 55% by weight, based on the total weight of the preparation.

[0024] Preferred embodiments of the present invention (emulsion) are characterized in that the preparation is in the form of an oil-in-water emulsion (O / W emulsion).

[0025] In such a case, it is advantageous according to the invention if the preparation contains one or more O / W emulsifiers selected from the group of compounds glyceryl stearate citrate, glyceryl stearate, glyceryl stearate (self-emulsifying), stearic acid, stearate salts, polyglyceryl-3 methylglycosederate, sodium cetearyl sulfate, potassium cetyl phosphate, polyglyceryl-6 stearate, polyglyceryl-6 behenate, polyglyceryl-10 stearate, sodium stearoyl glutamate, polyglyceryl-3 polyricinoleate (INCI: polyglyceryl-3 polyricinoleate), polyglyceryl-3 diisostearate and polyglyceryl-4 diisostearate / polyhydroxystearate / sebacate.

[0026] Furthermore, the advantageous embodiments according to the invention are characterized in that the preparation is free from polyacrylates, cross-linked acrylate / C10-C30 alkyl acrylate polymers, vinylpyrrolidone / hexadecene copolymers, 3-(4-methylbenzylidene)-camphor, 2-hydroxy-4-methoxybenzophenone (INCI: oxybenzone), 4-methoxycinnamic acid 2-ethylhexyl ester (INCI: octyl methoxycinnamate), ethylhexyl 2-cyano-3,3-diphenyl acrylate (INCI: octocrylene), parabens (in particular methyl, propyl and butyl paraben), methylisothiazolinone, chloromethylisothiazolinone, DMDM ​​hydantoin, mineral oils, mineral waxes and silicone oils.

[0027] However, it is advantageous in the sense of the present invention if the preparation contains one or more diols selected from the group of compounds 2-methyl-1,3-propanediol, propane-1,2-diol, butane-1,2-diol, pentane-1,2-diol, hexane-1,2-diol, octane-1,2-diol, decane-1,2-diol.

[0028] It is also advantageous according to the invention if the preparation contains one or more compounds selected from the group consisting of hexyl salicylate, 2-isobutyl-4-hydroxy-4-methyltetrahydropyran, further adipic acid diesters (other than dibutyl adipate), methylheptenone, alpha-isomethyl ionone, coumarin, hexyl cinnamal, limonene, linalool, diethyl succinate, hydroxyisohexyl 3-cyclohexene carboxaldehyde, menthyl PCA, citronellyl methyl crotonate, benzyl benzoate, benzyl alcohol, benzyl cinnamate, benzyl salicylate, citronellol, eugenol, and geraniol.

[0029] Furthermore, it is advantageous according to the present invention if the preparation contains 4-hydroxyacetophenone. In such a case, it is preferred according to the invention if the preparation contains 4-hydroxyacetophenone in a concentration of 0.1 to 0.5 wt%, based on the total weight of the preparation.

[0030] Furthermore, the cosmetic preparation according to the invention can contain the ingredients commonly used in cosmetics.

[0031] comparative test

[0032] Four percent bis-ethylhexyloxyphenol methoxyphenyl triazine is dissolved in C12-15 alkyl benzoates at 80°C. Then, 0.5 percent vanillin is added at room temperature. This solution is stored at room temperature and exposed to light. After two months of storage, distinct crystals have formed in the light pattern, which are also visible to the naked eye. Four percent bis-ethylhexyloxyphenol methoxyphenyl triazine is dissolved in dipropylene glycol dibenzoates and benzyl benzoates at 80°C. Then, 0.5 percent vanillin is added at room temperature. This solution is stored at room temperature and exposed to light. Even after six months of storage, no crystals are visible in the light pattern.

[0033] Examples

[0034] The following examples are intended to illustrate the present invention without limiting it. Unless otherwise stated, all quantities, proportions, and percentages are based on the weight and total quantity or total weight of the preparations.

[0035]

Claims

Patent claims 1. Cosmetic preparation containing 4-Hydroxy-3-methoxybenzaldehyde (INCI: vanillin), 2,4-bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: bis-ethylhexyloxyphenol methoxyphenyl triazine), Dipropylene glycol dibenzoate (INCI: Dipropylene Glycol Dibenzoate) and benzyl benzoate (INCI: Benzyl Benzoate).

2. Cosmetic preparation according to claim 1, characterized in that the preparation contains 4-hydroxy-3-methoxybenzaldehyde (INCI: Vanillin) in a concentration of 0.0002 to 1.5 wt%, based on the total weight of the preparation.

3. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains 2,4-Bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}- 6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis- Ethylhexyloxyphenol methoxyphenyl Triazine) in a concentration of 0.5 to 9.5 wt%, based on the total weight of the preparation.

4. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains dipropylene glycol dibenzoate (INCI: Dipropylene Glycol Dibenzoate) in a concentration of 0.5 to 10% by weight, based on the total weight of the preparation.

5. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains benzyl benzoate (INCI: Benzyl Benzoate) in a concentration of 0.0001 to 0.1 wt%, based on the total weight of the preparation.

6. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains Ci2-is-alkylbenzoate in a concentration of at most 10% by weight, based on the total weight of the preparation.

7. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains (2-[-4-(Diethylamino)-2-hydroxybenzoyl] Benzoic acid hexyl ester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), 2,4,6- Tris-[anilino-(p-carbo-2'-ethyl-T-hexyloxy)]-1,3,5-triazine (INCI: Ethylhexyl Triazone) and / or 4-(tert-Butyl)-4'-methoxydibenzoylmethane (INCI Butyl Methoxydibenzoylmethane).

8. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains ethylhexylglycerin.

9. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains ethylhexylglycerin in a concentration of 0.01 to 0.75 wt%, based on the total weight of the preparation.

10. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains ethanol.

11. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains ethanol in a concentration of 3 to 55% by weight, based on the total weight of the preparation.

12. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation is in the form of an emulsion and, preferably, in the form of an oil-in-water emulsion (O / W emulsion).

13. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains one or more O / W emulsifiers selected from the group consisting of the compounds glyceryl stearate citrate, glyceryl stearate, glyceryl stearate (self-emulsifying), stearic acid, stearate salts, polyglyceryl-3 methylglycosederate, sodium cetearoyl sulfate, potassium cetyl phosphate, polyglyceryl-6 stearate, polyglyceryl-6 behenate, polyglyceryl-10 stearate, sodium stearoyl glutamate, polyglyceryl-3 polyricinoleate (INCI: polyglyceryl-3 polyricinoleate), polyglyceryl-3 diisostearate and polyglyceryl-4 diisostearate / polyhydroxystearate / sebacate.

14. Cosmetic preparation according to one of claims 1 to 11, characterized in that the preparation is in the form of an ethanolic solution.

15. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation is free from polyacrylates, cross-linked acrylate / C10-C30 alkyl acrylate polymers, vinylpyrrolidone / hexadecene copolymers, 3-(4-methylbenzylidene) camphor, 2-hydroxy-4-methoxybenzophenone (INCI: oxybenzone), 4-methoxycinnamate-2-ethylhexyl ester (INCI: octyl methoxycinnamate), ethylhexyl-2-cyano-3,3-diphenyl acrylate (INCI: octocrylene), parabens (in particular methyl, propyl and butyl paraben), methylisothiazolinone, chloromethylisothiazolinone, DMDM ​​hydantoin, mineral oils, mineral waxes and silicone oils.

16. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains one or more diols selected from the group of compounds 2-methyl-1,3-propanediol, propane-1,2-diol, butane-1,2-diol, pentane-1,2-diol, hexane-1,2-diol, octane-1,2-diol, decane-1,2-diol.

17. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains one or more compounds selected from the group consisting of hexyl salicylate, 2-isobutyl-4-hydroxy-4-methyltetrahydropyran, further adipic acid diesters (other than dibutyl adipate), methylheptenone, alpha-isomethyl ionone, coumarin, hexyl cinnamal, limonene, linalool, diethyl succinate, hydroxyisohexyl 3-cyclohexene carboxaldehyde, menthyl PCA, citronellyl methyl crotonate, benzyl benzoate, benzyl alcohol, benzyl cinnamate, benzyl salicylate, citronellol, eugenol, and geraniol.

18. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains 4-hydroxyacetophenone.

19. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains 4-hydroxyacetophenone in a concentration of 0.1 to 0.5 wt%, based on the total weight of the preparation.

Citation Information

Patent Citations

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    DE102016000349A1

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