Compositions comprising a specific hyperbranched copolymer and 1,3-propanediol and / or N-hydroxyoctanamide

Abstract

The present invention relates to a composition comprising a specific hyperbranched copolymer (HBC) of monomeric dodecenyl succinic anhydride, diisopropanolamine and bis(dimethylaminopropyl)amine, and comprising the compounds 1,3-propanediol and / or N-hydroxyoctanamide. It has been found that the hyperbranched copolymer synergistically enhances the antimicrobial action of 1,3-propanediol and / or N-hydroxyoctanamide.

Description

Field of the Invention

[0001] The present invention relates to the field of antimicrobial agents, and in particular to the field of cosmetic compositions. Background Art

[0002] Antimicrobial agents are known ingredients for stabilizing compositions, and in particular cosmetic compositions, by reducing microbial growth. When using cosmetics, reducing the growth of microorganisms is crucial for the safety and health of consumers. By reducing the growth of microorganisms, the shelf life of cosmetics can be extended. Since the use of certain antimicrobial agents is under public discussion, reducing antimicrobial agents is a strong desire, especially in the cosmetic industry.

[0003] EP 2 794 729 B1 discloses the preparation of specific hyperbranched polyesters, which can be used as flocculants in paper production and dishwashing detergents.

[0004] EP 2 296 619 B1 discloses that specific hyperbranched copolymers have a beneficial effect in shampoos for increasing hair volume.

[0005] 1,3 - propanediol and N - hydroxyoctanamide are known compounds used as active antimicrobial aids in cosmetic compositions. Summary of the Invention

[0006] Therefore, the problem to be solved by the present invention is to provide a composition with enhanced antimicrobial properties.

[0007] It has surprisingly been found that the compositions according to the present invention are capable of solving this problem. It has been particularly observed that specific hyperbranched copolymers can enhance the antimicrobial action of antimicrobial agents, especially those used in cosmetic compositions. This effect is a synergistic effect of the specific hyperbranched copolymers on the antimicrobial effect of the antimicrobial agents. This surprising finding is very advantageous because the present invention can separately achieve higher stability, longer shelf life, to reduce the antimicrobial agents in the composition, and especially in cosmetic compositions, while maintaining antimicrobial properties.

[0008] The present invention includes other aspects and particularly preferred embodiments. Detailed Description

[0009] In a first aspect, the present invention relates to a composition comprising:

[0010] a) a hyperbranched copolymer (HBC), which is a hyperbranched copolymer of the following monomers:

[0011] (i) dodecenyl succinic anhydride,

[0012] (ii) Diisopropanolamine,

[0013] (iii) Bis(dimethylaminopropyl)amine,

[0014] The hyperbranched copolymer has end groups of the following formula:

[0015]

[0016] and a molecular weight Mn between 1200 g / mol and 4000 g / mol;

[0017] and

[0018] b) 1,3 - Propanediol and / or N - Hydroxyoctanamide.

[0019] The term "molecular weight Mn" represents the number - average molecular weight.

[0020] The terms "preparation" or "formulation" are equivalent to the term "composition" herein.

[0021] The term "antimicrobial agent" is used herein for organic chemicals that reduce microbial growth. However, for the present invention, monohydroxy - C1 - C6 alkanes, such as methanol, ethanol, propanol, or isopropanol, are not considered antimicrobial agents. For clarity, it is noted that antioxidants are not regarded as antimicrobial agents.

[0022] 1,3 - Propanediol has the formula 1,3 - Propanediol can be readily commercially available from different suppliers.

[0023] N - Hydroxyoctanamide (CAS - Nr. 7377 - 03 - 9) is readily commercially available.

[0024] The hyperbranched copolymer (HBC) is preferably prepared by the following consecutive steps:

[0025] a1) Polymerizing monomer (i), monomer (ii), and monomer (iii) to obtain a polyesteramide with dimethylamino end groups having the formula

[0026]

[0027] a2) Quaternizing the dimethylamino groups of the polyesteramide from step a1) with 2 - chloroacetate, especially sodium 2 - chloroacetate.

[0028] Details of the polymerization step a1) for obtaining the corresponding polyesteramide with dimethylamino end groups having the formula are disclosed, for example, by EP 2 794 729 B1.

[0029] Preferably, in the polymerization step a1), the monomer (iii) is added to the mixture of monomers (ii) and (iii) under stirring, and then heated.

[0030] EP 2 794 729 B1 also discloses the details of the quaternization step a2). Accordingly, the entire content of EP 2 794 729 B1 is incorporated herein by reference.

[0031] Preferably, the molar ratio of monomer (i) to monomer (ii) is between 5:1 and 0.5:1, especially between 4:1 and 1:1, preferably between 3:1 and 3:2.

[0032] More preferably, the molar ratio of monomer (i) to monomer (iii) is between 5:1 and 0.5:1, especially between 3:1 and 1:1, preferably between 2.5:1 and 1.1:1.

[0033] The number-average molecular weight M of the hyperbranched copolymer (HBC) n is preferably between 1400 g / mol and 3000 g / mol, preferably between 2100 g / mol and 2400 g / mol.

[0034] Preferably, the hyperbranched copolymer (HBC) is polyquaternium-110, CAS number 1323977-82-7.

[0035] The composition comprises 1,3-propanediol and / or N-hydroxyoctanamide.

[0036] In a preferred embodiment, the composition comprises 1,3-propanediol and does not comprise N-hydroxyoctanamide. In another preferred embodiment, the composition comprises N-hydroxyoctanamide and does not comprise 1,3-propanediol.

[0037] In another preferred embodiment, the composition comprises 1,3-propanediol and N-hydroxyoctanamide.

[0038] Preferably, the composition comprises 1,3-propanediol and N-hydroxyoctanamide. In the case where 1,3-propanediol and N-hydroxyoctanamide coexist, preferably the ratio of 1,3-propanediol to N-hydroxyoctanamide > 1, especially > 3. In a highly preferred embodiment, the composition comprises a mixture of 1,3-propanediol and N-hydroxyoctanamide, which can be obtained commercially under the trade name Zeastat TM from Inolex.

[0039] The weight ratio of the hyperbranched copolymer (HBC) to 1,3-propanediol and / or N - hydroxyoctanamide is preferably in the range of between 1:30 and 30:1, more preferably between 1:20 - 20:1, and even more preferably between 1:10 and 10:1.

[0040] In a preferred embodiment, the weight ratio of the hyperbranched copolymer (HBC) to 1,3 - propanediol and / or N - hydroxyoctanamide is greater than 1.

[0041] In one embodiment of the present invention, a composition of the hyperbranched copolymer (HBC) and 1,3 - propanediol and / or N - hydroxyoctanamide is used as an antimicrobial agent mixture. Such an antimicrobial agent mixture can be added to any other composition to enhance the resistance of the composition to microorganisms. Generally, the amounts of the hyperbranched copolymer (HBC) and 1,3 - propanediol and / or N - hydroxyoctanamide in such an antimicrobial agent mixture are quite large. In particular, based on the weight of the antimicrobial agent mixture, the weight of the hyperbranched copolymer (HBC) and 1,3 - propanediol and / or N - hydroxyoctanamide is greater than 10% by weight, particularly greater than 30% by weight, and preferably greater than 50% by weight. It is even possible that such an antimicrobial agent mixture consists of the hyperbranched copolymer (HBC) and 1,3 - propanediol and / or N - hydroxyoctanamide. Additionally, the antimicrobial agent mixture may further contain other antimicrobial agents.

[0042] The composition may additionally contain at least one other antimicrobial agent. Antimicrobial agents are known per se to those skilled in the art. However, the field of use limits the choice of antimicrobial agents, mainly due to regulatory issues. In the food and cosmetic fields, the choice of antimicrobial agents is rather limited.

[0043] Therefore, preferred antimicrobial agents applicable to the present invention are those acceptable in the food and cosmetic fields.

[0044] In a preferred embodiment of the preferred embodiments, the antimicrobial agent is selected from the group:

[0045] - monoesters or monoethers of glycerol;

[0046] - salts or esters of aromatic acids;

[0047] - alkyl aromatic alcohols;

[0048] - phenoxyalkanols;

[0049] - hydroxyacetophenone

[0050] - aliphatic diols; and

[0051] - hydroxamic acid.

[0052] Preferred monoesters or monoethers of glycerol are the glycerol monoesters or monoethers of formula (I)

[0053]

[0054] wherein R is C5-C 10 alkyl or C5-C 10 cycloalkyl, preferably C6-C9 alkyl or C6-C9 cycloalkyl, more preferably C6 alkyl or C8 alkyl or C6 cycloalkyl;

[0055] and wherein n is 1 or 0, preferably 0.

[0056] In the case where n = 0, R is preferably cyclohexyl or n-octyl or n-hexyl or branched octyl, preferably n-hexyl or ethylhexyl, more preferably 2-ethylhexyl. A preferred embodiment is caprylic acid glyceride.

[0057] In the case where n = 1, R is preferably branched or unbranched saturated or olefinically unsaturated heptyl or nonyl, preferably saturated or olefinically unsaturated heptyl or nonyl, more preferably n-octyl or n-nonyl, most preferably n-nonyl.

[0058] The glycerol monoesters or monoethers of formula (I) are preferably selected from: cyclohexyl glycerol, hexyl glycerol, ethylhexyl glycerol, decyl octanoate and glycerol decanoate, more preferably hexyl glycerol, ethylhexyl glycerol or decyl octanoate, most preferably ethylhexyl glycerol or hexyl glycerol. In the most preferred embodiment, the compound of formula (I) is 3-(2-ethylhexyloxy)-1,2-propanediol.

[0059] Preferred salts of aromatic acids are benzoates. Preferred salts are potassium salts or sodium salts, preferably sodium salts. Preferred esters of aromatic acids.

[0060] Preferred esters of aromatic acids are alkyl esters, especially C1-C6 alkyl esters of benzoic acid.

[0061] The most preferred salt or ester of aromatic acid is sodium benzoate.

[0062] Preferred alkyl aryl alcohols are alcohols having a C1-C6 alkylene group between the hydroxyl group of the alkyl aryl alcohol and the aromatic moiety, preferably an alcohol having a methylene group between the hydroxyl group of the alkyl aryl alcohol and the aromatic moiety. Benzyl alcohol is the most preferred alkyl aryl alcohol.

[0063] Phenol ether alcohols are alcohols containing an alcohol hydroxyl group and a phenol ether. The aromatic ring of phenol is optionally substituted. The ether oxygen and the hydroxyl group are preferably separated by a C2-C4 alkylene group, preferably separated by a vinyl group. Phenoxyethanol is the most preferred phenol ether alcohol.

[0064] Preferred hydroxyacetophenone is p-hydroxyacetophenone.

[0065] An aliphatic diol is an alkane containing two hydroxyl groups. These hydroxyl groups are preferably separated by a straight-chain or branched C2-C 10 alkylene group.

[0066] Preferred hydroxamic acids are hydroxamic acids of saturated C3-C 12 alkanoic acids. A preferred hydroxamic acid is N-hydroxyoctanamide ( = decanoyl hydroxamic acid).

[0067] Preferably, the antimicrobial agent is selected from: hexylglycerol, ethylhexylglycerol or glycerol caprate, sodium benzoate, benzyl alcohol, phenoxyethanol and N-hydroxyoctanamide.

[0068] More preferably, the antimicrobial agent is selected from: hexylglycerol, ethylhexylglycerol or glycerol caprate and N-hydroxyoctanamide.

[0069] The most preferred antimicrobial agent is hexylglycerol or ethylhexylglycerol.

[0070] In a preferred embodiment, the composition is a cosmetic composition.

[0071] Preferably, based on the total weight of the cosmetic composition, the amount of 1,3-propanediol and / or N-hydroxyoctanamide is 0.01 - 6.0% by weight, preferably 0.05 - 5.0% by weight, more preferably 0.1 - 3.0% by weight.

[0072] In the cosmetic composition, based on the total weight of the cosmetic composition, the amount of the hyperbranched copolymer (HBC) generally ranges between 0.005% by weight and 5.0% by weight, preferably between 0.05% by weight and 5.0% by weight, more preferably between 0.1% by weight and 3.0% by weight, and most preferably between 0.5% by weight and 2.5% by weight.

[0073] The cosmetic composition also preferably contains at least one emulsifier, preferably an anionic emulsifier. Preferably, the anionic emulsifier is selected from: potassium cetyl phosphate, disodium cetylstearyl sulfosuccinate, sodium stearoyl glutamate, sodium stearoyl lactate, glyceryl stearate citrate and sodium cocoyl isethionate.

[0074] Potassium cetyl phosphate is commercially available as K from DSM Nutritional Products Ltd Kaiseraugst of.

[0075] Based on the total weight of the cosmetic composition, the amount of the emulsifier preferably ranges between 0.1 - 6.0% by weight, more preferably between 0.25 - 5.0% by weight, especially between 0.5 - 4.0% by weight.

[0076] The composition preferably does not contain sulfates.

[0077] Accordingly, the cosmetic composition is particularly preferably free of sulfates selected from the group consisting of: alkyl sulfates, alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, and monoglyceride sulfates, and mixtures thereof.

[0078] As used herein, the term "free of", as in "free of sulfates", means that the corresponding substance is present in an amount of less than 0.5% by weight, particularly less than 0.1% by weight, and more particularly less than 0.05% by weight, relative to the weight of the composition. Preferably, "free of" means that the corresponding substance is completely absent from the composition.

[0079] The term "free of sulfates" is used herein to indicate that the composition is free of any anionic surfactant having a terminal anionic group of the following formula

[0080]

[0081] The cosmetic composition is preferably free of cationic emulsifiers. Typical examples of such cationic emulsifiers are isostearamidopropyldimethylamine, stearalkonium chloride, stearamidoethyldiethylamine, behentrimonium methosulfate, behenoyl oxy PG - trimethyl ammonium chloride, cetyltrimethylammonium bromide, behenamidopropyldimethylamine behenate, brassicamidopropyldimethylamine, stearamidopropyldimethylamine, cocoamidopropyl PG - dimethyl ammonium chloride, distearoylethyl hydroxyethyl methyl ammonium methosulfate, dicocooylethyl hydroxyethyl methyl ammonium methosulfate, distearoylethyl dimethyl ammonium chloride, shea butteramidopropyltrimonium chloride, behenamidopropyldimethylamine, brassicyl isoleucinate esylate, acrylamidopropyltrimonium chloride / acrylate copolymer, linoleamidopropyldimethylethyl ammonium ethyl sulfate, dimethyllauramine isostearate, isostearamidopropyl lauroyl acetyl dimethyl ammonium chloride, particularly behentrimonium chloride, distearoyl dimethyl ammonium chloride, cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, and palmamidopropyltrimonium chloride.

[0082] The cosmetic composition may also contain a cosmetic carrier, excipients, diluents, as well as additives and active ingredients commonly used in the skin care industry. Examples of such suitable for use in the cosmetic composition of the present invention are described, for example, in the International Cosmetic Ingredient Dictionary & Handbook by Personal Care, available through the online INFO BASE (http: / / online.personalcarecouncil.org / jsp / Home.jsp) provided by the Personal Care Products Council (http: / / www.personalcarecouncil.org / ), but are not limited thereto.

[0083] Such possible components of the cosmetic composition particularly enhance the performance and / or consumer acceptability, such as preservatives, antioxidants, fatty substances / oils, thickeners, softeners, sunscreens, moisturizers, fragrances, co-surfactants, fillers, polyvalent chelating agents, cationic polymers, non-ionic polymers or amphoteric polymers or mixtures thereof, acidifying agents or alkalizing agents, viscosity improvers and natural hair nutrients (such as botanicals, fruit extracts, sugar derivatives and / or amino acids) or any other components commonly formulated into cosmetic compositions. The necessary amounts of adjuvants and additives can be readily selected by those skilled in the art based on the desired product and will be illustrated in the examples, but are not limited thereto.

[0084] Additional components can be added to the oil phase, the aqueous phase or each separately as appropriate.

[0085] In a preferred embodiment, based on the total weight of the cosmetic composition, the cosmetic composition of the present invention contains 50% to 99%, preferably 60% to 98%, more preferably 70% to 98%, for example particularly 80% to 95% of the carrier.

[0086] In a particularly preferred embodiment, the carrier further comprises at least 40% by weight, more preferably at least 50% by weight, most preferably at least 55% by weight of water, for example particularly 55% to 90% by weight of water.

[0087] Furthermore, it is preferred that the cosmetic composition contains at least one ultraviolet (UV) filter. The UV filter can be a liquid or solid UV filter. The UV filter can be a UV-A or UV-B filter.

[0088] Suitable liquid UV filters absorb light in the UVB (280 - 315 nm) and / or UVA (315 - 400 nm) range and are liquid at ambient temperature (i.e., 25 °C). Such liquid UV filters are well known to those skilled in the art and particularly include cinnamates such as octyl methoxycinnamate ( MCX) and isoamyl methoxycinnamate (Neo E 1000); salicylates such as homosalate (3,3,5 - trimethylcyclohexyl 2 - hydroxybenzoate, HMS) and ethylhexyl salicylate (also known as ethylhexyl salicylate, 2 - ethylhexyl 2 - hydroxybenzoate, EHS); acrylates such as octocrylene (2 - ethylhexyl 2 - cyano - 3,3 - diphenylacrylate, 340) and ethyl 2 - cyano - 3,3 - diphenylacrylate; esters of benzylidene malonic acid, such as in particular dialkyl benzylidene malonates, such as bis(2 - ethylhexyl) 4 - methoxybenzylidene malonate and polysiloxane - 15 ( SLX); dialkyl naphthalenedicarboxylates such as diethylhexyl 2,6 - naphthalenedicarboxylate ( TQ); sylilidene malonates such as diethylhexyl sylilidene malonate ( ST liquid), and benzotriazolyl dodecyl p - cresol ( TL) and benzophenone - 3 and mexoryl sx.

[0089] Particularly advantageous liquid UV filters are octyl methoxycinnamate, homosalate, ethylhexyl salicylate, octocrylene, diethylhexyl 2,6 - naphthalenedicarboxylate, diethylhexyl sylilidene malonate, benzotriazolyl dodecyl p - cresol, benzophenone - 3, mexoryl sx, polysiloxane - 15 and mixtures thereof.

[0090] Suitable solid UV filters absorb light in the UVB and / or UVA range and are solid at ambient temperature (i.e., 25 °C). They are in particular solid organic UV filters. Particularly suitable solid UV filters are the group consisting of bis - ethylhexyloxyphenol methoxyphenyl triazine, butyl methoxydibenzoylmethane, methylene bis - benzotriazolyl tetramethylbutylphenol, diethylamino hydroxybenzoyl hexyl benzoate, ethylhexyl triazone, diethylhexyl butamido triazone and 4 - methylbenzylidene camphor.

[0091] The amount of the individual organic UV filter, based on the total weight of the cosmetic composition, is preferably in the range from 0.1% by weight to about 6% by weight, preferably in the range from 0.5% by weight to 5% by weight, most preferably in the range from 1% by weight to 4% by weight.

[0092] In the case of a sunscreen composition, the total amount of organic UV filters depends to a large extent on the targeted UV protection of the composition and, based on the total weight of the composition, the total amount of organic UV filters is generally in the range of between 1% and 50% by weight, preferably between 5% and 40% by weight.

[0093] A sunscreen with an SPF of 15 (SPF = sun protection factor), based on the total weight of the composition, contains, for example, a total amount of organic UV filters preferably in the range of between 4% and 20% by weight, more preferably between 7% and 15% by weight.

[0094] A sunscreen with an SPF of 30, based on the total weight of the composition, contains, for example, a total amount of organic UV filters preferably in the range of between 10% and 40% by weight, more preferably between 15% and 25% by weight.

[0095] A sunscreen with an SPF of 50, based on the total weight of the composition, contains, for example, a total amount of organic UV filters preferably in the range of between 15% and 50% by weight, more preferably between 20% and 40% by weight.

[0096] In all embodiments of the present invention, particularly suitable thickeners are xanthan gum, gellan gum and / or carboxymethyl cellulose. Most preferably, in all embodiments of the present invention, the thickener is xanthan gum or gellan gum. Other suitable thickeners are polyacrylates, which are commercially available, for example, under the trade name Carbomer, or acrylate / C10-30 alkyl acrylate crosslinked polymers or salts of polyacrylic acid or polyacrylamide.

[0097] Based on the total weight of the cosmetic composition, such thickeners are preferably used in an amount (total amount) selected from the range of 0.1% to 1% by weight, more preferably in an amount selected from the range of 0.1% to 0.5% by weight.

[0098] Preferably, the composition is free of polyvinylpyrrolidone (PVP), in particular alkylated polyvinylpyrrolidones, such as copolymers of N-vinylpyrrolidone with cetane or eicosene, which are commercially available, for example, as Antaron V-216 or Antaron V-220.

[0099] Generally, the cosmetic composition of the present invention has a pH in the range of 3 to 10, preferably in the range of 4 to 8, and most preferably in the range of 4 to 7.5. The pH is adjusted by methods known to those skilled in the art, such as by using acids (such as hydroxy acids, including glycolic acid, lactic acid, malic acid, citric acid, and tartaric acid) or bases (such as sodium hydroxide, potassium hydroxide, or ammonium hydroxide and mixtures thereof).

[0100] Preferably, in the composition of the present invention, citric acid is used in an amount of at least 0.0001% by weight, such as in an amount of 0.01 - 1% by weight, especially in an amount of 0.01% to 0.5% by weight, for pH adjustment.

[0101] The cosmetic composition preferably does not contain sulfates, and / or does not contain parabens, and / or does not contain silicone oils, and / or does not contain silicone surfactant, and / or does not contain methylisothiazolinone, and / or does not contain polyvinylpyrrolidone (PVP), especially does not contain alkylated polyvinylpyrrolidone.

[0102] The cosmetic composition is preferably a topical composition.

[0103] As used herein, the term "topical" should be understood herein to mean external application to keratinous substances, which are specifically skin, scalp, eyelashes, eyebrows, nails, mucous membranes, and hair, preferably skin.

[0104] Since topical compositions are intended for external application, it is well known that they contain a physiologically acceptable medium, that is, a medium compatible with keratinous substances (such as skin, mucous membranes, and keratin fibers). Specifically, the physiologically acceptable medium is a cosmetically acceptable carrier.

[0105] The term "cosmetically acceptable carrier" refers to all carriers and / or excipients and / or diluents conventionally used in topical cosmetic compositions, such as especially in sunscreen products.

[0106] The cosmetic composition is preferably a skin care composition.

[0107] In a further embodiment, the cosmetic composition is a decorative preparation or a functional preparation.

[0108] Examples of skin care compositions are especially photoprotective compositions, anti - aging compositions, compositions / preparations for treating photoaging, body oils, body lotions, body gels, care creams, skin ointments, skin powders, moisturizing gels, moisturizing sprays, facial and / or body moisturizers, skin tanning products (i.e., compositions for artificial / sunless tanning and / or browning of human skin), such as sunscreen, and brightening compositions.

[0109] Examples of functional products are cosmetic compositions containing active ingredients, such as but not limited to hormone products, vitamin products, plant extract products, anti-aging products, and / or anti-microbial (anti-bacterial or anti-fungal) products.

[0110] The cosmetic composition is preferably a skin care composition.

[0111] In a particular embodiment, the cosmetic composition is a sunscreen composition. A sunscreen composition is a light protection composition (sun protection product), such as a sun protection milk, a sun protection lotion, a sunscreen, a sun oil, a sun block, or a day cream having an SPF (sun protection factor). Sunscreens, sun lotions, sun protection milks, and sunscreen compositions are of particular interest.

[0112] The cosmetic composition of the present invention may be in the form of a suspension or dispersion in a solvent or fatty substance, or an emulsion or microemulsion (especially of the oil-in-water (O / W) or water-in-oil (W / O) type, water-in-silicone (Si / W) or silicone-in-water (W / Si) type, PIT emulsion, multiple emulsion (e.g., oil-in-water-in-oil (O / W / O) or water-in-oil-in-water (W / O / W) type), pickering emulsion, hydrogel, alcohol gel, lipid gel, single-phase or multi-phase solution or vesicular dispersion, or other common forms, which may also be applied as a mask or spray using a pen-type applicator.

[0113] In all embodiments of the present invention, the preferred cosmetic composition is an emulsion containing an oil phase and a water phase, such as especially O / W, W / O, Si / W, W / Si, O / W / O, W / O / W multiple emulsions or pickering emulsions.

[0114] Based on the total weight of the cosmetic composition, the total amount of the oil phase present in such an emulsion is preferably at least 10% by weight, e.g., in the range of 10% to 60% by weight, preferably in the range of 15% to 50% by weight, and most preferably in the range of 15% to 40% by weight.

[0115] Based on the total weight of the cosmetic composition, the amount of the water phase present in such an emulsion is preferably at least 20% by weight, e.g., in the range of 40% to 90% by weight, preferably in the range of 50% to 85% by weight, and most preferably in the range of 60% to 85% by weight.

[0116] The cosmetic composition may be in the form of a liquid, emulsion, thickened emulsion, gel, cream, milk, ointment, or paste.

[0117] More preferably, the cosmetic composition of the present invention is in the form of an oil-in-water (O / W) emulsion, which comprises an oil phase dispersed in an aqueous phase in the presence of an O / W or Si / W emulsifier. The preparation of such oil-in-water emulsions is well known to those skilled in the art.

[0118] The composition in the form of an O / W emulsion of the present invention can be provided, for example, in all the formulation forms of an O / W emulsion, such as in the form of a serum, an emulsion or a cream, and they are prepared according to conventional methods. The composition which is the subject of the present invention is preferably intended for external application and can in particular constitute a dermatological or cosmetic composition, such as a dermatological or cosmetic composition which is intended, for example, to protect human skin against the adverse effects of ultraviolet radiation (anti-wrinkle, anti-aging, moisturizing, sun protection, etc.).

[0119] Preferably, the cosmetic composition is a shampoo or a hair conditioner.

[0120] Preferably, the cosmetic composition is a hair care composition.

[0121] Preferably, the cosmetic composition is a shampoo or a hair conditioner.

[0122] More preferably, the cosmetic composition is an external composition applied to human skin, scalp and / or hair.

[0123] It has surprisingly been found that the hyperbranched copolymer (HBC) enhances the antimicrobial action of the antimicrobial agent in the cosmetic composition.

[0124] Accordingly, another aspect of the present invention relates to the use of a hyperbranched copolymer (HBC) for enhancing the antimicrobial action of 1,3-propanediol and / or N-hydroxyoctanamide, said hyperbranched copolymer being a hyperbranched copolymer of the following monomers:

[0125] (i) dodecenyl succinic anhydride,

[0126] (ii) diisopropanolamine,

[0127] (iii) bis-dimethylaminopropylamine,

[0128] The hyperbranched copolymer has end groups of the following formula:

[0129]

[0130] and a molecular weight Mn between 1200 g / mol and 4000 g / mol.

[0131] It has been specifically observed that for the antimicrobial effect, the microorganisms are selected from: Kocuria rhizophila, Staphylococcus aureus, Enterobacter gergoviae, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Pseudomonas fluorescens, Pseudomonas putida, Aspergillus brasiliensis, Penicillium pinophilum, and Candida albicans, especially against Escherichia coli.

[0132] The enhancement of the antimicrobial effect of 1,3-propanediol and / or N - hydroxyoctanamide by the hyperbranched copolymer (HBC) can be an enhancement in both the cosmetic and pharmaceutical senses.

[0133] Preferably, the use is a non - therapeutic use.

[0134] In a cosmetic composition, the non - therapeutic use is preferably a cosmetic use, such as for maintaining skin homeostasis and / or balancing the skin microbiome and / or the hair microbiome.

[0135] It has been observed that when the above - mentioned hyperbranched copolymer (HBC) is added to a cosmetic composition containing 1,3 - propanediol and / or N - hydroxyoctanamide, the antimicrobial effect is significantly enhanced. In other words, by additionally adding the hyperbranched copolymer (HBC) to a cosmetic composition containing 1,3 - propanediol and / or N - hydroxyoctanamide, a lower number of microbial growths are observed compared to not using the said hyperbranched copolymer (HBC). The above - mentioned hyperbranched copolymer (HBC) has a synergistic effect on the antimicrobial effect of 1,3 - propanediol and / or N - hydroxyoctanamide in the composition, especially in a cosmetic composition.

[0136] This is also very advantageous in the following way: by adding an effective amount of the above - mentioned hyperbranched copolymer (HBC), the amount of 1,3 - propanediol and / or N - hydroxyoctanamide can be reduced while maintaining the same antimicrobial effect.

[0137] It has been further observed that the antibacterial effect is particularly evident in the aqueous phase. This is very advantageous because it is well - known that the aqueous phase of a product is usually the most vulnerable to microbial growth.

[0138] Examples

[0139] The present invention is further illustrated by the following experiments. These examples are illustrative only and are not intended to limit the scope of the present invention in any way.

[0140] Preparation of Hyperbranched Copolymer (HBC1)

[0141] The hyperbranched copolymer HBC1 of monomer dodecenyl succinic anhydride, diisopropanolamine and bis(dimethylaminopropyl)amine has been prepared according to Example 3 in EP 2 794 729 B1 using 237.59 g of N,N-bis(N’N’-dimethylaminopropyl)amine, 112.6 g of diisopropanolamine and 426.89 g of dodecenyl succinic anhydride. After heating and vacuum, a residual carboxylic acid content of <0.3 meq / g (titration analysis), AV = 9.8 mg KOH / g, and an amine content of 2.99 meq / g (titration analysis) were obtained, and the molecular weight Mn = 2240 Da. The product has been reacted with sodium chloroacetate in water and stirred at 80 °C until 1 1H-NMR analysis showed complete conversion of the chloroacetate to obtain the hyperbranched copolymer HBC1, which has end groups of the following formula:

[0142] And the molecular weight Mn is 2.3 kDa.

[0143] The hyperbranched copolymer HBC1 was used as a 50% aqueous solution in the following experiments. The amounts shown in Table 1 are based on the amount of polymer.

[0144] Antimicrobial Activity Test (24 hours Challenge test)

[0145] Since it is well known that the aqueous phase of a product is most susceptible to microbial growth, the antimicrobial efficacy was evaluated using a regulatory challenge test method similar to that for aqueous solutions (NF EN ISO11930).

[0146] Therefore, solutions of the amounts of HPC1 and / or 1,3-propanediol and / or N-hydroxyoctanamide shown in Table 1 were prepared under sterile conditions. For this purpose, they were dissolved in physiological serum containing 0.85 wt% NaCl. The solutions were placed in 96 deep-well plates (1.6 ml / well). The wells were contaminated with 6.3*10 5 cfu / ml or 4.5*10 4 cfu / ml of Escherichia coli or Aspergillus brasiliensis. After contamination, each well was mixed thoroughly to ensure uniform distribution of the microorganisms. Then each plate was incubated at 22 °C for 24 h. The (remaining) population was counted 24 hours after contamination and reported in Table 1.

[0147] Antimicrobial action in 24-hour screening tests using Escherichia coli in Table 1

[0148]

[0149] n.m.: Not measured.

[0150] The results in Table 1 clearly show that these specific copolymers, namely hyperbranched copolymers, enhance the antimicrobial action of 1,3-propanediol and / or N-hydroxyoctanamide. This effect is synergistic.

[0151] It has been observed that HPC1 and 1,3-propanediol and / or N-hydroxyoctanamide, especially in combination with N-hydroxyoctanamide, show enhanced antimicrobial effects in different cosmetic compositions such as shampoos or o / w skin lotions.

Claims

1. A composition, the composition comprising: a) A hyperbranched copolymer (HBC), the hyperbranched copolymer being a hyperbranched copolymer of the following monomers: (i) Dodecenyl succinic anhydride, (ii) Diisopropanolamine, (iii) Bis-dimethylaminopropylamine, The hyperbranched copolymer has end groups of the following formula: and a molecular weight Mn between 1200 g / mol and 4000 g / mol; and b) N-Hydroxyoctanamide.

2. The composition according to claim 1, wherein The hyperbranched copolymer (HBC) is prepared by the following consecutive steps: a1) Polymerize monomer (i), monomer (ii) and monomer (iii) to obtain a polyester amide with a dimethylamino end group having the formula ​ a2) Quaternization of the dimethylamino groups of the polyester amide in step a1) with 2-chloroacetate.

3. The composition according to claim 2, wherein The 2-chloroacetate is sodium 2-chloroacetate.

4. The composition according to claim 1 or 2, characterized in that, The molar ratio of monomer (i) to monomer (ii) is between 5:1 and 0.5:

1.

5. The composition according to claim 4, wherein The molar ratio of monomer (i) to monomer (ii) is between 4:1 and 1:

1.

6. The composition according to claim 4, wherein The molar ratio of monomer (i) to monomer (ii) is between 3:1 and 3:

2.

7. The composition according to claim 1 or 2, characterized in that, The molar ratio of monomer (i) to monomer (iii) is between 5:1 and 0.5:

1.

8. The composition according to claim 7, wherein The molar ratio of monomer (i) to monomer (iii) is between 3:1 and 1:

1.

9. The composition according to claim 7, wherein The molar ratio of monomer (i) to monomer (iii) is between 2.5:1 and 1.1:

1.

10. The composition according to claim 1 or 2, characterized in that, The number-average molecular weight M of the hyperbranched copolymer n is between 1400 g / mol and 3000 g / mol.

11. The composition according to claim 10, wherein The number-average molecular weight M of the hyperbranched copolymer n is between 2100 g / mol and 2400 g / mol.

12. The composition according to claim 1 or 2, characterized in that, The hyperbranched copolymer is polyquaternium-110.

13. The composition according to claim 1 or 2, characterized in that, The weight ratio of the hyperbranched copolymer (HBC) to N-hydroxyoctanamide is between 1:30 and 30:

1.

14. The composition according to claim 13, wherein The weight ratio of the hyperbranched copolymer (HBC) to N-hydroxyoctanamide is between 1:20 - 20:

1.

15. The composition according to claim 13, wherein The weight ratio of the hyperbranched copolymer (HBC) to N-hydroxyoctanamide is between 1:10 and 10:

1.

16. The composition according to claim 1 or 2, characterized in that, The composition is a cosmetic composition.

17. The composition according to claim 16, wherein Based on the total weight of the cosmetic composition, the amount of the hyperbranched copolymer (HBC) is between 0.005% by weight and 5.0% by weight.

18. The composition according to claim 17, wherein Based on the total weight of the cosmetic composition, the amount of the hyperbranched copolymer (HBC) is between 0.05% by weight and 5.0% by weight.

19. The composition according to claim 17, characterized in that, Based on the total weight of the cosmetic composition, the amount of the hyperbranched copolymer (HBC) is between 0.1% by weight and 3.0% by weight.

20. The composition according to claim 17, characterized in that, Based on the total weight of the cosmetic composition, the amount of the hyperbranched copolymer (HBC) is between 0.5% by weight and 2.5% by weight.

21. The composition according to claim 16, wherein, The cosmetic composition is a skin care composition.

22. The composition according to claim 16, wherein The cosmetic composition is a hair care composition.

23. The composition according to claim 16, wherein The cosmetic composition is a shampoo or a conditioner.

24. The composition according to claim 16, wherein, The cosmetic composition is a topical composition applied to human skin, scalp and / or hair.

25. The non-therapeutic use of a hyperbranched copolymer (HBC) for enhancing the antimicrobial action of N-hydroxyoctanamide, the hyperbranched copolymer being a hyperbranched copolymer of the following monomers: (i) Dodecenyl succinic anhydride, (ii) Diisopropanolamine, (iii) Bis-dimethylaminopropylamine, The hyperbranched copolymer has end groups of the following formula: and a molecular weight Mn between 1200 g / mol and 4000 g / mol.

26. The use according to claim 25, characterized in that, The use is a cosmetic use.

Images