Cosmetic preparation containing vanillin and butyl methoxydibenzoylmethane
A cosmetic preparation with 4-hydroxy-3-methoxybenzaldehyde and di(propylene glycol) dibenzoate stabilizes 4-(tert-butyl)-4'-methoxydibenzoylmethane, addressing crystallization issues and maintaining UV protection and sensory quality.
Patent Information
- Application Number
- PCT/EP2025/060021
- 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
Cosmetic preparations containing vanillin and 4-(tert-butyl)-4'-methoxydibenzoylmethane suffer from crystallization issues, leading to reduced UV protection and sensory degradation due to the precipitation of vanillin and other sparingly soluble compounds, especially at low temperatures.
A cosmetic preparation comprising 4-hydroxy-3-methoxybenzaldehyde, 4-(tert-butyl)-4'-methoxydibenzoylmethane, and di(propylene glycol) dibenzoate, with specific concentration ranges, prevents crystallization and maintains UV protection by stabilizing the UV filter.
The formulation effectively prevents crystallization of UV filters and maintains UV protection and sensory properties over extended periods, even at low temperatures.
Smart Images

Figure IMGF000007_0001 
Figure IMGF000008_0001
Abstract
Description
[0001] Description
[0002] COSMETIC PREPARATION WITH VANILLIN AND BUTYL METHOXYDIBENZOYLMETHANE
[0003] The present invention relates to a cosmetic preparation containing 4-hydroxy-3-methoxybenzaldehyde (INCI: Vanillin), 4-(tert-Butyl)-4'-methoxydibenzoylmethane (INCI Butyl Methoxydibenzoylmethane) and di(propylene glycol) dibenzoate (INCI Dipropylene Glycol Dibenzoate).
[0004] 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.
[0005] 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.
[0006] 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.
[0007] A disadvantage of the prior art, however, is that the perfume ingredient vanillin (4-hydroxy-3-methoxybenzaldehyde) tends to crystallize out of cosmetic preparations in the presence of the UV light filter 4-(tert-butyl)-4'-methoxydibenzoylmethane (INCI Butyl Methoxydibenzoylmethane). These crystallization nuclei then, in turn, cause other sparingly soluble, lipophilic compounds, especially 4-(tert-butyl)-4'-methoxydibenzoylmethane, to also crystallize. As a result, not only do the sensory properties of the preparation suffer from crystal formation, but the UV protection (especially UV-A protection) of the affected cosmetic preparation is also reduced or completely lost. To suppress crystallization phenomena of lipophilic UV light filters, the oil component C12-15 alkyl benzoate is commonly used, a compound that is particularly suitable for 4-(tert.-Butyl)-4'-methoxydibenzoylmethane to be kept 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), 4-(tert-butyl)-4'-methoxydibenzoylmethane (INCI: butyl methoxydibenzoylmethane), and C12-15 alkyl benzoate (especially at low storage temperatures), 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 4-(tert-Butyl)-4'-methoxydibenzoyl methane.
[0010] The problem is surprisingly solved by a cosmetic preparation containing 4-hydroxy-3-methoxybenzaldehyde (INCI: Vanillin), 4-(tert-Butyl)-4'-methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoylmethane) and di(propylene glycol)dibenzoate (INCI: Dipropylene Glycol Dibenzoate).
[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 0.2 wt%, based on the total weight of the preparation. The preferred concentration according to the invention is 0.0002 to 1.5 wt%, based on the total weight of the preparation.
[0012] Advantageous embodiments of the present invention are characterized in that the preparation contains 4-(tert-butyl)-4'-methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoylmethane) 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 0.5 and 5% by weight, based on the total weight of the preparation.
[0013] Furthermore, it is advantageous according to the invention if the preparation contains di(propylene glycol) dibenzoate (INCI: Dipropylene Glycol Dibenzoate) in a concentration of 0.5 to 10 wt%, based on the total weight of the preparation. The preferred concentration according to the invention is between 1.0 and 5.0 wt%, based on the total weight of the preparation.
[0014] 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.
[0015] 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.
[0016] In addition to 4-(tert-Butyl)-4'-methoxydibenzoylmethane, the preparation according to the invention can contain further UV filters.
[0017] 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 2,4-Bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1 ,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol methoxyphenyl Triazine).
[0018] The preparation according to the invention contains (2-[-4-(Diethylamino)-2-hydroxybenzoyl] benzoic acid hexyl ester (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate), this substance is advantageously used according to the invention in a concentration of 0.5 to 9.5 wt%, based on the total weight of the preparation.
[0019] 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 wt%, based on the total weight of the preparation.
[0020] If the preparation according to the invention contains 2,4-bis-{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine (INCI: Bis-Ethylhexyloxyphenol methoxyphenyl Triazine), this substance is advantageously used according to the invention in a concentration of 0.5 to 9.5 wt%, based on the total weight of the preparation. Furthermore, it is advantageous according to 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 wt%, based on the total weight of the preparation.
[0021] According to the invention, the preparation can be in two different dosage forms: as an ethanolic solution and as an emulsion. If the preparation is in the form of an ethanolic solution, the ethanol concentration is advantageously 30 to 55% by weight, 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 preparation 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] Advantageous embodiments of the present invention are 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).
[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. 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, adipic acid diesters, 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.
[0028] 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.
[0029] Furthermore, the cosmetic preparation according to the invention can contain the ingredients commonly used in cosmetics.
[0030] comparative experiment
[0031] Four percent butyl methoxydibenzoylmethane is dissolved in C12-15 alkyl benzoates at 80°C. Then, 0.5 percent vanillin is added at room temperature. This dissolved mixture 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.
[0032] Four percent butyl methoxydibenzoylmethane is dissolved in dipropylene glycol dibenzoate at 80°C. Then, at room temperature, 0.5 percent vanillin is added. This dissolved mixture is stored at room temperature and exposed to light. Even after six months of storage, no crystals are visible in the light test.
[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.
Claims
Patent claims 1. Cosmetic preparation containing 4-Hydroxy-3-methoxybenzaldehyde (INCI: vanillin), 4-(tert-butyl)-4'-methoxydibenzoylmethane (INCI: butyl methoxydibenzoylmethane) and di(propylene glycol) dibenzoate (INCI: dipropylene glycol dibenzoate).
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 4-(tert-Butyl)-4'-methoxydibenzoylmethane (INCI: Butyl Methoxydibenzoylmethane) in a concentration of 0.5 to 10 wt%, preferably between 0.5 and 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 di(propylene 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 wt%, 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 2,4-Bis-{[4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1 ,3,5-triazine (INCI: Bis- Ethylhexyloxyphenol methoxyphenyl Triazine).
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 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.
14. 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.
15. 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.
16. 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, adipic acid diesters, 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.
17. Cosmetic preparation according to one of the preceding claims, characterized in that the preparation contains 4-hydroxyacetophenone.
18. 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
Cited By
Cosmetic preparation for priming prior to the application of make-up
WO2026166880A1