Method for stabilizing combination of ascorbic acid and ferulic acid

Abstract

The present invention relates to a process for preparing a cosmetic composition comprising ascorbic acid or one of its derivatives and ferulic acid or one of its derivatives, the process comprising temporarily mixing (i) a first aqueous composition comprising one of ascorbic acid or its derivatives and one of polyquaternium-67; (ii) a second composition comprising ferulic acid or one of its derivatives in at least one diol. The invention also relates to a method for caring for keratin materials, in particular the skin, comprising preparing a mixture and then applying the mixture.

Description

Technical Field

[0001] This invention relates to a method for preparing a composition that ensures stable association between ascorbic acid or one of its derivatives and ferulic acid or one of its derivatives. Background Technology

[0002] In cosmetic applications, ascorbic acid (vitamin C) is often added as an active agent due to its collagen-stimulating properties, which improve skin firmness. Ascorbic acid is also known for its antioxidant properties. Ferulic acid or its derivatives are also commonly used to improve the texture, hydration, evenness, softness and / or evenness, transparency and / or radiance of damaged skin.

[0003] However, ascorbic acid and ferulic acid are compounds that are difficult to stabilize in aqueous media, and their stability conditions differ. Specifically, the optimal stability condition for ascorbic acid is pH 6, while the optimal stability condition for ferulic acid is pH less than 4. Co-preparations of these two acids do not share a common pH range.

[0004] Therefore, there is a need for an aqueous cosmetic composition comprising ascorbic acid and ferulic acid that is stable over a period of at least one month. There is also a need for improved packaging suitable for the easy preparation of said aqueous cosmetic composition, and packaging that allows for optimal stability conditions for ascorbic acid and ferulic acid. Summary of the Invention

[0005] The purpose of this application is to address the stabilization incompatibility of the combination of ascorbic acid and ferulic acid in the same product and / or packaging.

[0006] Surprisingly, the applicant discovered that combining a composition containing one of the ascorbic acid or its derivatives and polyquaternium-67 with a composition containing one of the ferulic acid or its derivatives and a glycolic solvent via a temporary process enabled the production of compositions that were stable for at least 30 days.

[0007] Therefore, the present invention relates to a method for preparing a composition comprising one of ascorbic acid or a derivative thereof and one of ferulic acid or a derivative thereof, the method comprising temporarily mixing (i) and (ii): (i) A first aqueous composition comprising one of ascorbic acid or a derivative thereof and polyquaternium-67, (ii) A second composition comprising one of ferulic acid or a derivative thereof in at least one diol.

[0008] Specifically, the temporary mixing is carried out at ambient temperature.

[0009] The term "ambient temperature" refers to a temperature of approximately 20°C to 25°C.

[0010] After mixing the first composition (i) and the second composition (ii), the pH of the cosmetic composition according to the invention is 4 to 8, preferably 5 to 7. Preferably, the pH of the composition according to the invention is 6.

[0011] The composition according to the invention is stable.

[0012] Preferably, the cosmetic composition of the present invention is stable at ambient temperature.

[0013] The composition is considered stable when its macroscopic appearance (clarity and uniformity) remains unchanged after at least 30 days. In particular, the compositions according to the invention have a transparent and uniform appearance.

[0014] For the purposes of this invention, the term "transparent" refers to a composition having a transparent appearance.

[0015] For the purposes of this invention, the term "homogeneous" refers to a composition consisting of a single phase, in other words, it is single-phase.

[0016] Specifically, for the purposes of this invention, a composition is considered stable when it is stable with respect to the chemical loss of ascorbic acid and ferulic acid at ambient temperature, preferably measured by liquid chromatography combined with UV detection, for up to 1 month (30 days), preferably up to 2 months (60 days), and more preferably up to 3 months (90 days). More specifically, a composition is considered stable when, at ambient temperature, the chemical loss of ascorbic acid is less than 20% p / p and the chemical loss of ferulic acid is less than 20% w / w for up to 1 month (30 days), preferably up to 2 months (60 days), and more preferably up to 3 months (90 days).

[0017] To evaluate the stability of the composition, the chemical loss of ascorbic acid and ferulic acid is preferably measured as follows: The chemical losses of ascorbic acid and ferulic acid were measured using liquid chromatography combined with UV detection based on the following parameters: chromatographic column : ACQUITY UPLC HSS T3 RP18 100x2.1mm, 1.7µm Elution solution 0.006 mol / L disodium hydrogen phosphate buffer, pH 2.1 / ACN (20 / 80 v / v) Flow rate 0.35 mL / min Injection volume 1µl temperature 50°C λ detection UV 200 to 300nm: Ascorbic acid was extracted at 250 nm, and ferulic acid was extracted at 320 nm.

[0018] This invention also relates to stable cosmetic compositions, particularly cosmetic compositions that are stable for at least 30 days at room temperature with respect to the chemical loss of ascorbic acid and ferulic acid (hereinafter referred to as "stable cosmetic compositions"), which comprise, by weight relative to the total composition: 0.1 to 15% by weight of ascorbic acid or one of its derivatives, and 0.01 to 1% by weight of ferulic acid or one of its derivatives, The pH of the composition is 4 to 8, preferably 5 to 7, and most preferably 6.

[0019] According to embodiments, the compositions according to the invention are substantially free of tocopherol. "Substantially free of tocopherol" means that, relative to the total weight of the composition, the tocopherol concentration of the compositions according to the invention is less than or equal to 2% by weight, preferably less than or equal to 1% by weight, and more preferably from 0.01% by weight to 2% by weight. Preferably, the compositions according to the invention are completely free of tocopherol.

[0020] According to embodiments, the compositions according to the invention are substantially free of vitamin E. "Substantially free of vitamin E" means that, relative to the total weight of the composition, the vitamin E concentration of the compositions according to the invention is less than or equal to 2% by weight, preferably less than or equal to 1% by weight, and more preferably from 0.01% to 2% by weight. Preferably, the compositions according to the invention are completely free of vitamin E.

[0021] The present invention also relates to a cosmetic method for caring for keratin materials, particularly skin, the method comprising: (1) a method for preparing a cosmetic composition according to the present invention, and then (2) applying the cosmetic composition to a keratin material, particularly skin.

[0022] Specifically, step (2) of applying the cosmetic composition is performed no later than one month (i.e. no later than 30 or 31 days) after step (1) of preparing the composition.

[0023] Furthermore, the present invention also relates to the use of the composition in the cosmetic field, particularly for use in the care of keratin materials, especially for the skin.

[0024] For the purposes of this invention, the term "keratin material" refers to skin.

[0025] The term "skin" refers to facial skin and / or body skin, as well as scalp.

[0026] The present invention also relates to a kit for caring for and / or treating keratin materials, particularly skin, comprising: (i) a first aqueous composition comprising one of ascorbic acid or a derivative thereof and polyquaternium-67, and (ii) a second composition comprising one of ferulic acid or a derivative thereof in at least one diol.

[0027] First aqueous composition (i) The present invention comprises (i) a first aqueous composition comprising one of ascorbic acid or a derivative thereof and polyquaternium-67.

[0028] one of the following: ascorbic acid or its derivatives The ascorbic acid according to the present invention can be in D form or L form.

[0029] Preferably, the ascorbic acid used for the purposes of this invention corresponds to L-ascorbic acid or vitamin C. It has a structure according to formula (I): [Chemical Formula 1]

[0030] The composition (i) may also contain an ascorbic acid derivative, which is an ascorbate salt, such as sodium ascorbate, magnesium ascorbate phosphate or sodium ascorbate, and glycosylated ascorbic acid.

[0031] Composition (i) may also contain ascorbic acid derivatives. Examples include ascorbic acid glycoesters and phosphorylated ascorbic acid metal salts.

[0032] In the context of ascorbic acid glycoesters, references may be made to glycosylated, mannosylated, fructosylated, fucoidosylated, galactosylated N-acetylglucosamines, N-acetylmuramic acid derivatives, and mixtures thereof, particularly ascorbic acid-2-glucosidoside or 2-O-α-D-glucopyranosyl or 6-O-β-D-galactopyranosyl of L-ascorbic acid. These compounds and their preparation methods are specifically described in references EP 487 404, EP 425 066, and J05213736.

[0033] Phosphorylated ascorbic acid metal salts can be selected from alkali metal ascorbic acid phosphates, alkaline earth metal ascorbic acid phosphates, and transition metal ascorbic acid phosphates.

[0034] Ascorbic acid, specifically as commercial brand ascorbic acid (L), was purchased from Reckon Organics, and as brand ascorbic acid ultrafine powder, from DSM Nutritional Products.

[0035] Suitable ascorbic acid derivatives according to the present invention may be selected from 5,6-di-O-dimethylsilyl ascorbate sold by Exsymol under the brand name PRO-AA, DL-α-tocopherol-dl-ascorbic acid potassium phosphate sold by Senju Pharmaceutical under the brand name Sepivital EPC, magnesium ascorbic acid phosphate sold by Roche under the brand name STAY-C 50, sodium ascorbic acid phosphate, and ascorbate glucoside sold by Hayashibara.

[0036] Preferably, relative to the total weight of composition (i), the first composition (i) contains 0.12% to 20% by weight, preferably 1% to 18% by weight, preferably 10% to 17% by weight of one of the derivatives of ascorbic acid or thereof.

[0037] The stable cosmetic composition according to the invention comprises, relative to the total weight of the composition, 0.1% to 15% by weight, preferably 1% to 14% by weight, and more preferably 5% to 13% by weight of one of the derivatives of ascorbic acid or thereof.

[0038] Polyquaternium-67 Preferably, relative to the total weight of composition (i), the first composition (i) contains 0.1% to 1% by weight, preferably 0.2% to 0.8% by weight, and preferably 0.2% to 0.5% by weight of polyquaternium-67.

[0039] Polyquaternium-67, for example, is sold by Amerchol (Dow Chemical) under the brand name Softcat Polymer SL-100.

[0040] Preferably, the stable cosmetic composition according to the invention comprises 0.1% to 1% by weight, preferably 0.2% to 0.8% by weight, preferably 0.2% to 0.6% by weight, and more preferably 0.2% to 0.5% by weight of polyquaternium-67, relative to the total weight of the composition.

[0041] water Preferably, relative to the total weight of composition (i), the first composition (i) contains at least 40% by weight of water, preferably at least 45% by weight of water, preferably at least 50% by weight of water, preferably at least 55% by weight of water, and preferably at least 60% by weight of water.

[0042] The water used can be sterile softened water and / or floral water, such as rose water, cornflower water, chamomile water, or linden water, and / or spring water or natural mineral water, such as Vittel water, water from the Vichy Basin, Uriage water, la Roche Posay water, la Bourboule water, Enghien-les-Bains water, Saint Gervais-les-Bains water, Néris-les-Bains water, Allevar-les-Bains water, Digne water, Maizières water, Neyrac-les-Bains water, Lons-le-Saunier water, and Les Eaux water. Bonnes, Rochefort, Saint Christau, Fumades, Tercis-les-bains, and Avène water. Preferably, the composition (i) according to the invention is an aqueous solution. Preferably, the composition according to the invention is a single-phase composition. The term "single-phase" means that the composition according to the invention does not have a dispersed phase in the form of droplets (also called a discontinuous phase) in the dispersed phase (also called a continuous phase). Such a composition may be referred to as a "serum". The term "serum" indicates a fluid, flowing composition.

[0043] solvent Preferably, the composition (i) according to the invention is completely free of water-soluble organic solvents.

[0044] Preferably, the term "water-soluble organic solvent" refers to an organic solvent selected from alcohols, polyols, and mixtures thereof.

[0045] In alcohols, C1-C can be mentioned. 10 More preferably, C1-C5 alcohols, such as ethanol, isopropanol, propanol and butanol.

[0046] The polyol may be selected from polyols having 2 to 20 carbon atoms, such as glycerol, diglycerol, propylene glycol, isopentyl glycol, dipropylene glycol, butanediol, octyl glycol, hexanediol, 1,3-propanediol, pentylene glycol, polyethylene glycol having 2 to 200 ethylene oxide units, and mixtures thereof.

[0047] In particular, composition (i) comprises at least one organic solvent selected from glycerol, pentylene glycol, octylene glycol and mixtures thereof.

[0048] Preferably, composition (i) comprises a mixture of glycerol, pentylene glycol and octylene glycol.

[0049] Preferably, relative to the total weight of composition (i), composition (i) according to the invention comprises 0.1% to 35% by weight, preferably 1% to 30% by weight, preferably 5% to 25% by weight, preferably 10% to 20% by weight, preferably 15% to 19% by weight of an organic solvent.

[0050] alkali The composition (i) may optionally contain at least one base.

[0051] An alkali can be an organic alkali or a mineral alkali.

[0052] Examples of organic bases include primary, secondary, or tertiary alkylamines, such as triethylamine or butylamine.

[0053] Examples of mineral alkalis include hydroxides of metals or ammonium, such as LiOH, NaOH, KOH, Ca(OH)2, NH4OH, Mg(OH)2, or Zn(OH)2.

[0054] Preferably, the alkali is selected from mineral alkalis, more preferably from alkali metal hydroxides, and more preferably sodium hydroxide or potassium hydroxide, with sodium hydroxide being advantageous.

[0055] Preferably, when composition (i) contains an alkali, composition (i) contains 0.1% to 10% by weight, preferably 0.5% to 6% by weight, preferably 1% to 5% by weight, preferably 2% to 4% by weight of the alkali relative to the total weight of composition (i).

[0056] The composition may also contain one or more additives commonly used in cosmetic compositions, preferably selected from surfactants, chelating agents, preservatives and fragrances.

[0057] Preferably, among the additives that may be used are adenosine, sodium hyaluronate, trisodium ethylenediamine disuccinate, hydroxyacetophenone, or mixtures thereof.

[0058] Second composition (ii) The present invention includes a second composition (ii) which contains one of ferulic acid or a derivative thereof in at least one diol.

[0059] ferulic acid The composition (ii) according to the invention comprises one of ferulic acid or a derivative thereof.

[0060] Ferulic acid is the common name for [(hydroxy-4-methyl-3)-3-phenyl]-3-propen-2-ic acid. It has a structure according to formula (II): [Chemical Formula 2] (II) "Derivatives" of ferulic acid specifically refer to its esters and / or salts and / or plant extracts containing it.

[0061] As for the "esters" of ferulic acid, esters of ferulic acid and C1-C30 alcohols can be specifically mentioned, especially methyl ferulic acid, ethyl ferulic acid, isopropyl ferulic acid, octyl ferulic acid, and oryzanyl ferulate.

[0062] As for the "salts" of ferulic acid, organic ferulic acid salts, especially sodium salts, such as sodium ferulic acid and sodium isofrulic acid, are particularly noteworthy.

[0063] As "plant extracts" containing ferulic acid, rice, wheat, barley, oats, bark, poplar buds, asparagus, olives, and berries may be specifically mentioned. Preferably, the bran component of rice, wheat, barley, or oats is used. According to a specific embodiment, wheat bran extract will be used.

[0064] Preferably, the ferulic acid derivative is selected from esters of ferulic acid and C1-C30 alcohols, organic ferulic acid salts, plant extracts containing ferulic acid, and mixtures thereof.

[0065] Ferulic acid is particularly available from Oryza Oil & Fat Chemicals under the brand name Oryza Ferulix.

[0066] Preferably, relative to the total weight of composition (ii), the second composition (ii) according to the invention comprises 0.04% to 5% by weight, preferably 0.5% to 4% by weight, or even more preferably 1% to 3% by weight of one of ferulic acid or its derivatives.

[0067] The stable cosmetic composition according to the invention comprises, relative to the total weight of the composition, 0.01% to 1% by weight, preferably 0.1% to 0.8% by weight, and more preferably 0.3% to 0.7% by weight of ferulic acid or a derivative thereof.

[0068] Diol The composition (ii) according to the invention comprises at least one diol. The term "diol" means a diol in which the two hydroxyl groups are carried by two different carbon atoms.

[0069] The diol may be selected from polyols having 2 to 20 carbon atoms, such as glycerol, diglycerol, propylene glycol, isopentyl glycol, dipropylene glycol, butanediol, octyl glycol, hexanediol, 1,3-propanediol, pentylene glycol, polyethylene glycol having 2 to 200 ethylene oxide units, or mixtures thereof.

[0070] Preferably, the diol is dipropylene glycol.

[0071] Dipropylene glycol is exclusively available from Ineos under the brand name Dipropylene Glycol.

[0072] Preferably, relative to the total weight of composition (ii), composition (ii) according to the invention comprises at least 20% by weight, preferably at least 30% by weight, preferably at least 40% by weight, preferably at least 50% by weight, preferably at least 60% by weight, preferably at least 70% by weight, preferably at least 80% by weight, preferably at least 85% by weight, preferably at least 90% by weight, preferably at least 95% by weight, preferably at least 98% by weight of diol.

[0073] The compositions according to the present invention are readily available to those skilled in the art.

[0074] Unless otherwise stated, expressions “between… and…” and “ranging from… to…” should be understood to include limits. Detailed Implementation

[0075] The following examples are provided to provide a better understanding of the invention, but are not intended to limit it in any way. Raw materials are indicated by their chemical names or INCI names. Unless otherwise stated, the amounts shown are by weight % (%w / w) of the raw material relative to the total weight of the composition.

[0076] Example I- Preparation of the temporary composition according to the present invention The first composition (i) C1 based on ascorbic acid and the second composition (ii) C2 based on ferulic acid according to the present invention are prepared according to the components in Table 1 below: [Table 1]

[0077] Composition I1 (a stable cosmetic composition according to the invention) was then prepared by temporarily mixing 75% by weight of C1 and 25% by weight of C2 relative to the total weight of the mixture C1+C2. The resulting composition is as follows: [Table 2]

[0078] II- Stability of the temporary composition according to the invention The stability of composition I1 (a stable cosmetic composition according to the invention) was tested by repeated testing.

[0079] To evaluate the stability of the composition, the chemical loss of ascorbic acid and ferulic acid was assessed at ambient temperature on days 1, 4, 7, 14, 21, 30 and 60 after mixing C1+C2.

[0080] Measurement of chemical loss: The chemical losses of ascorbic acid and ferulic acid were measured using liquid chromatography combined with UV detection based on the following parameters: chromatographic column : ACQUITY UPLC HSS T3 RP18 100x2.1mm, 1.7µm Elution solution 0.006 mol / L disodium hydrogen phosphate buffer, pH 2.1 / ACN (20 / 80 v / v) Flow rate 0.35 mL / min Injection volume 1µl temperature 50°C λ detection UV 200nm to 300nm: Ascorbic acid was extracted at 250 nm, and ferulic acid was extracted at 320 nm.

[0081] The results are summarized in Table 3 below: [Table 3]

[0082] Vitamin C (ascorbic acid) can be stable at ambient temperature for up to 2 months (chemical loss <20%).

[0083] Ferulic acid maintained its stability at ambient temperature for up to one month, meeting the requirements (10% loss at 3 weeks; 13% loss at 4 weeks). From 2 months onwards, the chemical loss reached 30%, which was no longer acceptable.

[0084] In summary, good stability of ascorbic acid and ferulic acid in composition I1 was observed for up to 1 month at ambient temperature after the first use of the temporary mixture at pH 6 (5 drops daily).

[0085] II- Stability of the temporary composition according to the invention with temperature variation The stability of composition I1 (a stable cosmetic composition according to the invention) was tested according to two independent tests at ambient temperature (AT) and 45°C.

[0086] To evaluate the stability of the composition, the chemical loss of ascorbic acid and ferulic acid was evaluated at ambient temperature or 45°C on days 7, 14, 21, 28, 21 and 60 after mixing C1+C2 (as described above).

[0087] Test 1: [Table 4]

[0088] Test 2: [Table 5]

[0089] Observations show that ascorbic acid remains stable for up to two months (with a loss of less than 9%) at ambient temperature, while ferulic acid remains stable for at least four weeks.

[0090] At 45°C, ascorbic acid remained stable for at least 4 weeks, but ferulic acid degraded significantly from the first week (30% loss). After 2 months at 45°C, a loss of over 96% of ferulic acid was observed.

[0091] III- Stability of compositions C1 and C2 according to the present invention The stability of compositions C1 and C2 was tested at 45°C using two independent tests.

[0092] To evaluate the stability of these compositions, the chemical loss of ascorbic acid and ferulic acid was evaluated on day 0 and day 30 after each of compositions C1 and C2 was prepared at 45°C (as described above).

[0093] [Table 6]

[0094] At 45°C, vitamin C (ascorbic acid) is stable in composition C1 for at least 2 months (30 days) with a chemical loss of << 20%. At 45°C, ferulic acid is stable in composition C2 for at least 2 months (30 days) with a chemical loss of << 20%.

[0095] In summary, ascorbic acid and ferulic acid are stable for at least 2 months in compositions C1 and C2, respectively, at 45°C, and are therefore more stable at room temperature.

Claims

1. A method for preparing a cosmetic composition comprising one of ascorbic acid or a derivative thereof and ferulic acid or a derivative thereof, said method comprising temporarily mixing in (i) and (ii): (i) A first aqueous composition comprising one of ascorbic acid or a derivative thereof and polyquaternium-67, (ii) A second composition comprising one of ferulic acid or a derivative thereof in at least one diol.

2. The method according to claim 1, wherein, The first composition (i) contains, relative to the total weight of composition (i), 0.12 to 20% by weight, preferably 1 to 18% by weight, preferably 10 to 17% by weight of ascorbic acid or a derivative thereof.

3. The method according to claim 1 or 2, wherein, The first composition (i) contains at least 40% by weight of water, preferably at least 45% by weight, preferably at least 50% by weight, preferably at least 55% by weight, and preferably at least 60% by weight of water relative to the total weight of the composition (i).

4. The method according to any one of the preceding claims, wherein, The first composition (i) contains 0.1 to 1% by weight, preferably 0.2 to 0.8% by weight, and preferably 0.2 to 0.5% by weight of polyquaternium-67 relative to the total weight of composition (i).

5. The method according to any one of the preceding claims, wherein, The second composition (ii) comprises, relative to the total weight of composition (ii), 0.04% to 5% by weight, preferably 0.5% to 4% by weight, preferably 1% to 3% by weight of one of ferulic acid or its derivatives.

6. The method according to any one of the preceding claims, wherein, Relative to the total weight of composition (ii), the second composition (ii) comprises at least 20% by weight, preferably at least 30% by weight, preferably at least 40% by weight, preferably at least 50% by weight, preferably at least 60% by weight, preferably at least 70% by weight, preferably at least 80% by weight, preferably at least 85% by weight, preferably at least 90% by weight, preferably at least 95% by weight, preferably at least 98% by weight of a diol, preferably selected from polyols having 2 to 20 carbon atoms, such as glycerol, diglycerol, propylene glycol, isopentyl glycol, dipropylene glycol, butanediol, octyl glycol, hexanediol, 1,3-propanediol, pentylene glycol, polyethylene glycol having 2 to 200 ethylene oxide units, and mixtures thereof, preferably the diol being polyethylene glycol.

7. The method according to any one of the preceding claims, wherein, The obtained cosmetic composition has a pH of 4 to 8, preferably 5 to 7, and most preferably 6.

8. A method for caring for keratin materials, particularly skin, comprising: (1) Prepare a cosmetic composition according to any one of the preceding claims, and then (2) apply the cosmetic composition to a keratin material, particularly the skin.

9. The method of care according to claim 8, wherein step (2) of applying the cosmetic composition is performed no later than 30 days after step (1) of preparing the composition.

10. A stable cosmetic composition, comprising, relative to the total weight of the composition: 0.1 to 15% by weight of ascorbic acid or one of its derivatives, and 0.01 to 1% by weight of ferulic acid or one of its derivatives, and 0.1 to 1% by weight of polyquaternium-67, The pH of the composition is 4-8, preferably 5-7, and more preferably 6.

11. The cosmetic composition according to claim 10, characterized in that, The cosmetic composition is stable at ambient temperatures, specifically between 20°C and 25°C.

12. A kit for caring for and / or treating keratin materials, particularly skin, comprising: (i) a first aqueous composition comprising one of ascorbic acid or a derivative thereof and polyquaternium-67, and (ii) a second composition comprising one of ferulic acid or a derivative thereof in at least one diol.

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