Patent Application
20240207153
The Invention relates to desferrioxamines and compositions containing UV light protection filters.
Desferrioxamines form a substance category within the iron-binding siderophores. A review is found, for example, in Hider and Kong, Chemistry and Biology of Siderophores, Natural Product Reports (2010), 27(5), 637-657.
Desferrioxamine B, also known as deferoxamine, is described for application In cosmetic applications. Thus, DE10050155 discloses cosmetic and dermatological preparations with a content of desferrioxamine B.
The need for sunscreen formulations with a high sun protection factor (SPF) has constantly increased In recent years. Formulations exhibit constantly increasing concentrations of UV light protection filters, in order to satisfy the demand for formulations with very high SPFs. Unfortunately, soiling by such sunscreen formulations of textiles can often be difficult to remove, since UV light protection filters exhibit a high affinity for the fibres.
EP 3 228 299 discloses, for solving this problem, a process for making it easier for cosmetic preparations containing UV light protection filters to be washed out from textiles, characterized in that 4-hydroxyacetophenone is added to the cosmetic.
It Is an object of the present invention to make available compositions containing UV light protection filters which make it possible to more effectively wash out UV light protection filters from textiles.
It has been found, surprisingly, that the compositions described subsequently, containing at least one desferrioxamine and/or at least one acid addition product of a desferrioxamine or salts thereof, are able to achieve the object addressed by the invention.
The present invention accordingly relates to compositions containing at least one desferrioxamine and/or at least one acid addition product of a desferrioxamine or salts thereof and also to a UV light protection filter substance according to claim 1.
The present invention additionally relates to a method for decreasing discolourations of a textile caused by a sunscreen formulation according to claim 9.
The present invention additionally relates to the use of at least one desfenioxamine and/or at least one acid addition product of a desferrioxamine or salts thereof, in particular desferrioxamine B, for decreasing discolourations of a textile according to claim 9.
The present invention additionally relates to the use of at least one desferroxamine and/or at least one acid addition product of a desferrioxamine or salts thereof for more effectively washing out a UV light protection filter substance according to claim 10.
An advantage of the present invention Is that desferrioxamine and/or acid addition products of the desferrioxamine or salts thereof are better at keeping UV light protection filter substances in solution.
An additional advantage of the present invention is that the compositions according to the invention are characterized by a relatively low oily and satisfactorily absorbing feeling on the skin.
An additional advantage of the present invention is that the compositions according to the invention exhibit an excellent shelf life with regard to the emulsion stability and accordingly can be kept for a long time.
An additional advantage of the present invention is that the compositions according to the invention have good spreadability and thus achieve a homogeneous distribution of the sunscreen factors on the skin.
An additional advantage of the present invention is that the compositions according to the invention have a particularly insignificant Influence on the viscosity of a formulation and can be used over a broad pH range.
An additional advantage of the present invention is that the compositions according to the invention can be incorporated in a particularly easy and stable manner in cosmetic formulations.
An additional advantage of the present invention is that the compositions according to the invention exhibit particularly good skin sensorics and contribute to a reduction in the tackiness of sunscreen filters and reduce the whitening of the skin.
An additional advantage of the present invention is that the compositions according to the invention contribute to an improvement in the thermal stability of the formulation.
An additional advantage of the present invention is that the compositions according to the invention impart an excellent colour stability in the formulation.
An additional advantage of the present invention is that the compositions according to the invention exhibit improved shelf lives with regard to growth of certain microorganisms and accordingly can be kept for a long time.
Unless otherwise indicated, all stated percentages (%) are percentages by weight.
The present invention accordingly relates to a composition comprising
Any desferrioxamine and acid addition product of a desferrioxamine or salt thereof, and also mixtures thereof, can be present according to the invention in component A).
Preferred desferrioxamines in this connection are chosen from desferrioxamine A1A, desferrioxamine A1B, desferrioxamine A2, desferrioxamine B, desferrioxamine D1, desferrioxamine D2, desferrioxamine E, desferrioxamine Et1, desferrioxamine Et2, desferrioxamine Et3, desferrioxamine G1, desferrioxamine G2A, desferrioxamine G2B, desferrioxamine G2C, desferrioxamine H, desferrioxamine N, desferrioxamine P1, desferrioxamine T1, desferrioxamine T2, desferrioxamine T3, desferrioxamine T7, desferrioxamine T8, desferrioxamine Te1, desferrioxamine Te2, desferrioxamine Te3, desferrioxamine X1, desferrioxamine X2, desferrioxamine X3 and desferrioxamine X4, preferably desferrioxamine B, desferrioxamine D1, desferrioxamine D2, desferrioxamine E and desferrioxamine H, particularly preferably desferrioxamine B and desferrioxamine E.
For the nomenclature, compare If necessary Hider and Kong, Chemistry and Biology of Siderophores, Natural Product Reports (2010), 27(5), 637-657.
It is preferred according to the invention for the acid addition product of the desferrioxamine or salts thereof to be chosen from acid addition products of the acids chosen from formic acid, aminooxyacetic acid, amino acids, anthraquinonecarboxylic acid, succinic acid, aqueous hydrochloric acid, acetic acid, folic acid, glutaric acid, hydroxamic acid, malonic acid, methanesulfonic acid, nalidixic acid, N-(methylamino)benzoic acid, phenylsuccinic acid, phenylglutaric acid, phosphorous acid, phosphoric acid, hydrogen chloride, sulfurous acid, sulfuric acid, tartaric acid and citric acid, hydrogen chloride, methanesulfonic acid, acetic acid and amino acids being particularly preferred.
A preferred composition according to the invention is characterized In that component A) is present in an amount of 0.005% by weight to 10.0% by weight, preferably from 0.05% by weight to 5.0% by weight, particularly preferably from 0.1% by weight to 1.0% by weight, the percentages by weight being with respect to the total composition.
It is preferred according to the invention for component B) of the composition according to the invention to comprise at least two, preferably at least three, particularly preferably at least four, UV light protection filter substances.
It is preferred according to the invention for the component B) to comprise a UV light protection filter substance from the group of organic UV light protection filter substance.
Organic substances which are capable of absorbing ultraviolet radiation and re-emitting the absorbed energy in the form of longer-wave radiation, e.g. heat, for example can be present as UV light protection filter substances in component B).
UVB filters can be oil-soluble or water-soluble. Mention may be made, as oil-soluble UVB light protection filters, e.g., of:
3-benzylidenecamphor derivatives, e.g. 3-(4-methybenzylidene)camphor (INCI: 4-Methylbenzyldene Camphor), 4-aminobenzoic acid derivatives, such as, e.g., 2-ethyNexyl 4-(dimethylamino)benzoate (INCI: Ethylhexyl Dimethyl PABA), 2-hydroxyethyl 4-{bis[2-(2-hydroxyethoxy)ethyl]amino}benzoate (INCI: PEG-25 PABA), cinnamic acid esters, such as, e.g., 2-ethylhexyl 4-methoxycinnamate (INCI: Ethylhexyl Methoxycinnamate), Isopentyl 4-methoxycinnamate (INCI: Isoamyl p-Methoxycinnamate), 2-ethylhexyl 2-cyano-3,3-diphenylacrylate (INCI: Octocrylene), salicylic acid esters, such as, e.g., 2-ethylhexyl salicylate (INCI: Ethylhexyl Salicylate), homomenthyl salicylate (INCI: Menthyl Salicylate), 3,3,5-trimethylcyclohexyl salicylate (INCI: Homosalate), 2,2′,2″-nitilotriethanol 2-hydroxybenzoate (1:1) (INCI: TEA-Salicylate), benzophenone derivatives, such as, e.g., 2-hydroxy-4-methoxybenzophenone (INCI: Benzophenone-3), 2,2′-dihydroxy-4-methoxybenzophenone (INCI: Benzophenone-8), 2-hydroxy-4-methoxy-4-methylbenzophenone (INCI: Benzophenone-10), triazine derivatives, such as, e.g., tris(2-ethylhexyl) 4,4′,4″-(1,3,5-triazine-2,4,6-triyltriimino)tribenzoate (INCI: Ethylhexyl Triazone, obtainable, e.g., under the trade name Uvinul T 150 from BASF), iscotrizinol (INCI: Diethylhexyl Butamido Triazone) and 2,4,6-tri(4-biphenylyl)-1,3,5-triazine (INCI: Tris-Biphenyl Triazine).
An additional UVB filter is the (3-(4-(2,2-bis(ethoxycarbonyl)inyl)phenoxyopenyl)methoxysioxane/dimethylsioxane copolymer (INCI: Polysilicone-15), which can be obtained, for example, under the trade name Parsol SLX. Possible water-soluble UVB light protection filters are, for example:
salts of 2-phenybenzimidazole-5-sulfonic acid, such as its alkali metal, alkaline earth metal, ammonium, alkylammonium, alkanolammonium and glucammonium salts, and also the sulfonic acid itself with the INCI name Phenylbenzimidazole Sulfonic Acid, sulfonic acid derivatives of benzophenone, such as, e.g., 5-benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid (INCI: Benzophenone-4) and its salts, benzenesulfonic acid derivatives of 3-benzylidenecamphor, such as, e.g., 4-[(E)-4,7,7-trimethyl-3-oxobicyclo[22.1]hept-2-ylidene)methyl]benzenesulfonic acid (INCI: Benzylidene Camphor Sulfonic Acid) and its salts.
Possible typical oil-soluble UVA/broadband light protection filters are, for example, benzylmethane derivatives, such as, for example, 1-(4-methoxyphenyl)-3-[4-(2-methyl-2-propanyl)phenyl]-1,3-propanedione (INCI: Butyl Methoxydibenzoylmethane) or 1-(4-4-isopropylphenyl)-3-phenyl-1,3-propanedione (INCI: Isopropyl Dibenzoylmethane), triazine derivatives, such as, e.g., 2,2′-[6-(4-methoxyphenyl)-1,3,5-triazine-2,4-diyl]bis{5-[(2-ethylhexyl)oxy]phenol} (INCI: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine, obtainable, e.g., under the trade name Tinosorb S from BASF), N,N′-bis[4-[5-(1,1-dimethylpropyl)-2-benzoxazolyl]phenyl]-N″-(2-ethylhexyl)-1,3,5-triazine-2,4,6-triamine (INCI: Ethylhexyl Bis-isopentylbenzoxazolylphenyl Melamine, obtainable under the trade name Uvasorb K2A from 3V Sigma) and benzophenone derivatives, such as, e.g., hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (INCI: Diethylamino Hydroxybenzoyl Hexyl Benzoate).
Possible water-soluble UVA/broadband light protection filters are, for example: 3,3′-(1,4-phenylenedimethylene)bis(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-ylmethanesulfonic acid) and the salts thereof, in particular the corresponding sodium, potassium or triethanolammonium salt, which is also described as benzene-1,4-di(2-oxo-3-bornylidenemethyl-10-sulfonic acid) and has the INCI description Terephthalylidene Dicamphor Sulfonic Acid (obtainable under the trade name Mexoryl SX), 2,2′-(1,4-phenylene)bis(6-sulfo-1H-benzimidazole-4-sulfonic acid) and its salts, the corresponding sodium, potassium or triethanolammonium salts, e.g. disodium 2,2′-(1,4-phenylene)bis(6-sulfo-1H-benzimidazol-4-sulfonate) with the INCI description Disodium Phenyl Dibenzimidazole Tetrasulfonate, trade name e.g. Neo Heliopan AP.
Additional UVA/broadband filters are, e.g. 2,2′-methylenebis[6-(2H-benzotriazol-2-yl)-4-(2,4,4-trimethyl-2-pentanyl)phenol] (INCI: Methylene Bis-Benzotriazolyl Tetramethylbutylphenol, obtainable, e.g., under the trade name Tinosorb M from BASF), 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propyl]phenol (INCI: Drometrizole Trisiloxane, trade name: Mexoryl XL), (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-aminobenzoate (INCI: Menthyl Anthranilate) and 2-ethoxyethyl (2E)-3-(4-methoxyphenyl)acrylate (INCI: Cinoxate).
The UV filters can also obviously be present In mixtures In the compositions according to the invention.
In addition to the soluble substances mentioned, Insoluble pigments are also possible for this purpose, namely finely dispersed metal oxides or salts, such as, for example, titanium dioxide, zinc oxide, iron oxide, aluminium oxide, cerium oxide, zirconium oxide, silicates (talc), barium sulfate and zinc stearate. The insoluble pigments in component B) are preferably selected from the group consisting of titanium dioxide, zinc oxide, aluminium oxide, barium sulfate and zinc stearate The particles should in this connection exhibit a mean diameter of less than 100 nm, e.g. between and 50 nm and in particular between 15 and 30 nm. They can exhibit a spherical shape; however, it is also possible to use those particles which have an ellipsoidal shape or a shape which deviates in another way from the spherical form. However, also possible are micronized organic pigments, such as, for example, 2,2-methylenebis[6-(2H-benzotriazol-2-yl)-4-(2,4,4-trimethyl-2-pentanyl)phenol] (INCI: Methylene Bis-Benzotriazolyl Tetramethylbutylphenol, obtainable, e.g., under the trade name Tinosorb M from BASF) with a particle size of <200 nm, which can be obtained, e.g., as a 50% aqueous dispersion.
Furthermore, additional suitable UV light protection filters can be taken from the review by P. Finkel in SÖFW Journal, 122, 543 (1996), or from the chapter, “The Chemistry of Ultraviolet Filters”, by NA. Sheath In “Principles and Practice of Photoprotection”, S. Q. Wang and H. W. Lim (eds.), Springer International Publishing, Switzerland, 2016.
It is preferred according to the invention for the component B) not to contain a UV light protection filter substance from the group octyl methoxycinnamate, methylbenzylidenecamphor and butyl methoxydibenzoylmethane.
It is preferred according to the invention for the component B) to comprise a UV light protection filter substance from the group of the triazine derivatives.
A preferred composition according to the invention is characterized in that component B) comprises a UV light protection filter substance from the group,
The compositions according to the invention can, e.g., comprise at least one further additional component chosen from the group of the
emollients, emulsifiers, coemulsifiers, thickeners/viscosity regulators/stabilizers, antioxidants, hydrotropes (or polyols), solids and fillers, pearlescent additives, insect repellents, self-tanning agents, preservatives, conditioners, perfumes, colourants, cosmetic active substances, care additives, superfatting agents and solvents.
Substances which can be used as exemplary representatives of the individual groups are known to a person skilled in the art and can, for example, be taken from German Application DE 102008001788.4. This patent application Is Incorporated in the current document as reference and is accordingly to be regarded as part of the disclosure.
As regards further optional components and also the amounts used of these components, reference is expressly made to the relevant handbooks known to a person skilled in the art, e.g. K. Schrader, “Grundlagen und Rezepturen der Kosmetika [Fundamentals and Formulations of Cosmetics]”, 2nd edition, pages 329 to 341, Hüthig Buch Verlag, Heidelberg.
The amounts of the respective additives depend on the intended use.
Typical starting formulations for the relevant applications are known prior art and are contained for example in the brochures of the manufacturers of the relevant base materials and active substances. These existing formulations can generally be adopted unchanged. However, if necessary, for adjustment and optimization, the desired modifications can be executed in a straightforward manner through simple tests.
Compositions according to the invention can, for example, be used as skin care, face care, head care, body care, Intimate care, foot care, hair care, nail care, dental care or oral care products.
Compositions according to the invention can, for example, be used in the form of an emulsion, a suspension, a solution, a cream, a salve, a paste, a gel, an oil, a powder, an aerosol, a stick, a spray, a cleansing product, a make-up or sunscreen preparation or a face lotion.
Preferred compositions according to the invention are emulsions, in particular chosen from oil-in-water emulsions and water-in-oil emulsions, oil-In-water emulsions being particularly preferred.
The present invention additionally relates to a process for decreasing discolourations of a textile caused by a sunscreen formulation comprising the process stage
Making available the sunscreen formulation
in the form of a composition containing
According to the invention, the method according to the invention preferably comprises in addition the process stage
Washing the textile with an aqueous composition, preferably an aqueous surfactant composition.
The compositions mentioned above as preferred in connection with the compositions according to the invention are preferably used according to their preference in the method according to the invention. The present invention additionally relates to the use of at least one substance chosen from desferrioxamines and acid addition products of a desferrloxamine or salts thereof, in particular desferrioxamine B, for decreasing discolourations of a textile caused by a sunscreen formulation containing at least one UV light protection filter substance.
The present invention additionally relates to the use of at least one substance chosen from desferrioxamines and acid addition products of a desferrioxamine or salts thereof, in particular desferrioxamine B, for improving the ability to wash out at least one UV light protection filter substance from a textile.
In the uses according to the invention, the components mentioned above in connection with the compositions according to the invention as components preferably present are preferably used.
The present invention Is described by way of example in the examples cited below, without the invention, the scope of application of which results from the entirety of the description and from the claims, being restricted to the embodiments mentioned in the examples.
The following figures are an integral part of the examples:
For the comparison of the ability of marks of light protection filter to be washed out from textiles, different cosmetic compositions
(Formulations 1-6) were prepared and 0.6 g was applied evenly In circular fashion (diameter d=45 mm) to a cotton fabric. Subsequently, the fabric was dried under laboratory conditions at 40° C. for 1 h in a drying cupboard and subsequently covered with baking paper, and ironed with an iron at level 2 for 1 min. Subsequently, the colour intensity of the marks was measured (first measurement) by means of a colorimeter (NR145, 3nh).
The colorimeter measurement was used for the recording or the comparison of the discolouration before and after the washing of the textiles. The principle of the colour measurement is based on an illumination of the sample and on the recording of the reflectance spectrum and on the direct conversion into colorimetric data. The data determined describe the colour of a sample In the L*a*b* colour space (also: CIELAB; DIN EN ISO 11664-4). In this connection, the a coordinate gives the colour intensity and chromaticity between green and red, the b coordinate gives the colour intensity and the chromaticity between blue and yellow and the L coordinate gives the lightness. For the comparison, the AE value between the discolourations and the untreated fabric was determined before and after washing and used as a measure of the Euclidean colour difference to each other.
Subsequent to the first measurement, the fabric was washed at 60° C. (1 h; 60° C.; Ariel Colour powder), and subsequently again without detergent (1 h; 60° C.; water). After washing, the fabric was dried in air under laboratory conditions and the colour intensity of the marks was measured again (second measurement) by means of a colorimeter (NR145, 3nh).
The formulation constituents In the following compositions (Formulations 1-6) are referred to in the form of the generally accepted INCI nomenclature with use of the English terms. All concentrations in the use examples are, unless otherwise indicated, given as % by weight.
In total, 3×6 OW emulsions (sunscreen creams) were prepared.
Formulation 1 comprised no UV filter (neg. control) and Formulations 2-6 contained five UV filters In different combinations. Each formulation was prepared each time without complexing agent, with EDTA and with desferrioxamine. The pH of all formulations was adjusted with citric acid to 5.5.
The results (
Following EP 3 228 299 (Example Formulation 2 from EP 3 228 299), cosmetic compositions (O/W sunscreen creams) were prepared with 4-hydroxyacetophenone (Formulation 7) and desferrioxamine B (Formulation 8) and both together (Formulation 9), and the ability to wash out light protection filter marks from textiles was investigated according to the methodology described above.
The formulation constituents in the following compositions (Formulation 7-9) are referred to in the form of the generally accepted INCI nomenclature. All concentrations in the use examples are, unless otherwise indicated, given as % by weight.
In total, 3 O/W emulsions (sunscreen creams) were prepared with the 6 UV filters Homosalate, Ethylhexyl Salicylate, Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine, Ethylhexyl Triazone, Butyl Methoxydibenzoylmethane and Phenylbenzimidazole Sulfonic Acid.
The formulation was each time prepared with 4-hydroxyacetophenone (Formulation 7), desferrioxamine (Formulation 8) and both raw materials (Formulation 9). The pH of all formulations was adjusted with NaOH to 7.3.
The results in
Following Example 1 and 2, cosmetic compositions (O/W sunscreen creams) were prepared with 4-hydroxyacetophenone, Disodium EDTA and desferrioxamine (according to the invention) and without any of the forementioned raw materials. The ability to wash off anorganic UV light protection filter marks from textiles was investigated according to the methodology described In Example 1.
The formulation constituents In the following compositions (Formulation 10-13) are referred to In the form of the generally accepted INCI nomenclature.
All concentrations In the examples are, unless otherwise indicated, given as % by weight.
In total, 4 OW emulsions (sunscreen creams) were prepared with 2 Insoluble, anorganic U filter pigments, the metal oxides Titanium dioxide and Zinc Oxide.
The formulation was each time prepared with 4-hydroxyacetophenone (Formulation 11), Disodium EDTA (Formulation 12) and desferrioxamine B (Formulation 13) and without any of the forementioned raw materials (Formulation 10). The pH of all formulations was adjusted to 5.5.
The results In
Sensory Improvements of a formulation according to the invention (Formulation 11 from Example 3) in comparison to a formulation without desferrioxamine (Formulation 10 from Example 3) are observed on a likert scale from 1 (very bad) to 5 (very good) by a group of 4 trained test persons, The sensory test results are summarized in Table 1.
The sunscreen formulation in accordance to the invention (Formulation 11) improves the spreadability, tackiness and skin feeling and reduces the whitening effect of the formulation in comparison to the vehicle formulation (Formulation 10) without desferrioxamine.
| Number | Date | Country | Kind |
|---|---|---|---|
| 21170621.3 | Apr 2021 | EP | regional |
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/EP2022/060388 | 4/20/2022 | WO |
