Compositions containing specific hyperbranched copolymers and 1,3-propanediol and / or N-hydroxyoctanamide

Abstract

The present invention relates to a composition comprising a specific hyperbranched copolymer (HBC) of the following monomers: dodecenylsuccinic anhydride, diisopropanolamine, and bis-dimethylaminopropylamine, and the compounds: 1,3-propanediol and / or N-hydroxyoctanamide, which has been found to synergistically enhance the antimicrobial activity of 1,3-propanediol and / or N-hydroxyoctanamide.

Description

Detailed Description of the Invention

[0001] [Technical field] The present invention relates to the field of antimicrobial agents, especially in the field of cosmetic compositions.

[0002] [Background of the invention] Antimicrobial agents are known ingredients for stabilizing compositions, especially cosmetic compositions, by reducing microbial growth. The reduction of microbial growth is essential for consumer safety and health when using cosmetics. By reducing microbial growth, the shelf life of cosmetics can be extended. The reduction of antimicrobial agents is highly desired, especially in the cosmetics industry, since the use of certain antimicrobial agents is controversial in the public.

[0003] EP 2794729 B1 discloses the preparation of certain highly branched polyesters which can be used as flocculants in paper making and dishwashing detergents.

[0004] EP 2296619 B1 discloses that certain highly branched copolymers have beneficial effects in shampoos for increasing hair volume.

[0005] 1,3 propanediol and N-hydroxyoctanamide are compounds known to be used as active antimicrobial adjuvants in cosmetic compositions.

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

[0007] Surprisingly, it has been found that the composition of claim 1 can solve this problem. In particular, it has been confirmed that certain hyper-branched copolymers can enhance the antibacterial activity of antibacterial agents, especially those used in cosmetic compositions. This effect is a synergistic effect of certain hyper-branched copolymers on the antibacterial activity of antibacterial agents. This surprising finding is highly advantageous, since the present invention allows for increased stability, increased shelf life, and reduced antibacterial agents in compositions, especially cosmetic compositions, while still maintaining antibacterial properties.

[0008] Further aspects of the invention are the subject matter of further independent claims. Particularly preferred embodiments are the subject matter of the dependent claims.

[0009] Detailed Description of the Invention In a first aspect, the present invention provides a method for producing a composition comprising the steps of: a) the following monomers: (i) dodecenylsuccinic anhydride; (ii) diisopropanolamine; (iii) Bis-dimethylaminopropylamine A highly branched copolymer (HBC) of the formula: [ka] and a molecular weight Mn of 1200 to 4000 g / mol; b) 1,3-propanediol and / or N-hydroxyoctanamide; The present invention relates to a composition comprising:

[0010] The term "molecular weight Mn" denotes the number average molecular weight.

[0011] The terms "manufacturing" or "formulation" are used equivalently with the term "composition" in this document.

[0012] The term "antimicrobial" is used in this document for organic chemicals that reduce the growth of microorganisms. However, monohydroxy-C1-C6 alkanes such as methanol, ethanol, propanol or / iso-propanol are not considered to be antimicrobials in the present invention. For clarity, it is worth noting that antioxidants are not considered to be antimicrobials.

[0013] 1,3 propanediol has the formula: [ka] 1,3 propanediol is readily available commercially from a variety of sources.

[0014] N-hydroxyoctanamide (CAS-Nr. 7377-03-9) is readily available commercially.

[0015] The hyperbranched copolymer (HBC) is preferably produced by the following sequential steps: a1) polymerizing monomer (i), monomer (ii) and monomer (iii) to form a compound represented by the formula: [ka] obtaining a polyesteramide having dimethylamino end groups of a2) quaternization of the dimethylamino groups of the polyesteramide of step a1) by means of 2-chloroacetate, in particular sodium 2-chloroacetate; Manufactured by.

[0016] The following formula: [ka] Details regarding the polymerization step a1), from which the respective polyesteramides having dimethylamino end groups of the formula (I) are obtained, are disclosed, for example, in EP 2 794 729 B1.

[0017] Preferably, in the polymerization step a1), monomer (iii) is added under stirring to a mixture of monomers (ii) and (iii), followed by heating.

[0018] Details of the quaternization step a2) are also disclosed in EP 2 794 729 B1, the entire content of which is therefore incorporated herein by reference.

[0019] The molar ratio of monomer (i):monomer (ii) is preferably 5:1 to 0.5:1, particularly preferably 4:1 to 1:1, and more preferably 3:1 to 3:2.

[0020] It is further preferred that the molar ratio of monomer (i):monomer (iii) is 5:1 to 0.5:1, particularly 3:1 to 1:1, and preferably 2.5:1 to 1.1:1.

[0021] The highly branched copolymer (HBC) preferably has a number average molecular weight M n It has a molecular weight of 1400 to 3000 g / mol, preferably 2100 to 2400 g / mol.

[0022] Preferably, the hyperbranched copolymer (HBC) is Polyquaternium-110, also identified by the CAS number 1323977-82-7.

[0023] The composition includes 1,3-propanediol and / or N-hydroxyoctanamide.

[0024] In one 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.

[0025] In yet another preferred embodiment, the composition includes both 1,3-propanediol and N-hydroxyoctanamide.

[0026] The composition preferably comprises 1,3-propanediol and N-hydroxyoctanamide, in the case of co-presence, preferably with a ratio of 1,3-propanediol to N-hydroxyoctanamide >1, in particular >3. In a highly preferred embodiment, the composition comprises a mixture of 1,3-propanediol and N-hydroxyoctanamide, commercially available under the trade name Zeastat™ from Inolex.

[0027] The weight ratio of the hyperbranched copolymer (HBC) to 1,3-propanediol and / or N-hydroxyoctanamide is preferably in the range of 1:30 to 30:1, more preferably 1:20 to 20:1, and even more preferably 1:10 to 10:1.

[0028] In a preferred embodiment, the weight ratio of the highly branched copolymer (HBC) to 1,3-propanediol and / or N-hydroxyoctanamide is greater than 1.

[0029] In one embodiment of the present invention, the composition of the hyper-branched copolymer (HBC) and 1,3-propanediol and / or N-hydroxyoctanamide is used as an antimicrobial mixture. Such an antimicrobial mixture can be added to any other composition to improve its resistance against microorganisms. Usually, the amount of the hyper-branched copolymer (HBC) and 1,3-propanediol and / or N-hydroxyoctanamide in such an antimicrobial mixture is substantial, in particular the weight of the hyper-branched copolymer (HBC) and 1,3-propanediol and / or N-hydroxyoctanamide is more than 10% by weight, in particular more than 30% by weight, preferably more than 50% by weight, based on the weight of the antimicrobial mixture. Such an antimicrobial mixture can even consist of the hyper-branched copolymer (HBC) and 1,3-propanediol and / or N-hydroxyoctanamide. Furthermore, the antimicrobial mixture can also contain further antimicrobial agents.

[0030] This composition may further comprise at least one additional antibacterial agent.Antibacterial agents are known per se to those skilled in the art.However, depending on the field of use, the choice of antibacterial agents is limited, mainly due to regulatory issues in particular.In the field of food and cosmetics, the choice of antibacterial agents is rather limited.

[0031] Therefore, preferred antimicrobial agents suitable for the present invention are antimicrobial agents that are acceptable in the food and cosmetic fields.

[0032] In one preferred embodiment, the antibacterial agent is: - monoesters or monoethers of glycerol; -salts or esters of aromatic acids; -Alkyl aryl alcohols; -phenol ether alcohols; -Hydroxyacetophenone aliphatic diols; and -Hydroxamic acid is selected from the group consisting of:

[0033] Preferred monoesters or monoethers of glycerol have the following formula (I): [ka] is a monoester or monoether of In the above formula, R is C5 to C 10 Alkyl group or C5-C 10 a cycloalkyl group, preferably a C6-C9 alkyl group or a C6-C9 cycloalkyl group, more preferably a C6 alkyl group or a C8 alkyl group or a C6 cycloalkyl group; and n is either 1 or 0, preferably 0.

[0034] When n=0, R is preferably a cyclohexyl or n-octyl or n-hexyl or branched octyl radical, preferably an n-hexyl radical or an ethylhexyl radical, more preferably a 2-ethylhexyl radical. A preferred embodiment is glyceryl caprylate.

[0035] When n=1, R is preferably a branched or unbranched saturated or olefinically unsaturated heptyl or nonyl group, preferably a saturated or olefinically unsaturated heptyl or nonyl group, more preferably an n-octyl or n-nonyl group, most preferably an n-nonyl group.

[0036] The monoester or monoether of glycerol of formula (I) is preferably selected from the group consisting of cyclohexylglycerin, hexylglycerin, ethylhexylglycerin, glyceryl caprate and glyceryl caprylate, more preferably hexylglycerin, ethylhexylglycerin or glyceryl caprate, most preferably ethylhexylglycerin or hexylglycerin. In a most preferred embodiment, the compound of formula (I) is 3-(2-ethylhexyloxy)-1,2-propanediol.

[0037] Preferred salts of aromatic acids are the salts of aromatic acids. Preferred salts are the potassium or sodium salts, preferably the sodium salt. Preferred esters of aromatic acids

[0038] Preferred esters of aromatic acids are the alkyl esters of benzoic acid, especially the C1-C6 alkyl esters.

[0039] The most preferred salt or ester of an aromatic acid is sodium benzoate.

[0040] Preferred alkyl aryl alcohols are those having a C1-C6 alkylene group, preferably a methylene group, between the hydroxyl group and the aromatic moiety of the alkyl aryl alcohol. Benzyl alcohol is the most preferred alkyl aryl alcohol.

[0041] Phenol ether alcohols are alcohols containing an alcoholic hydroxyl group of phenol and an ether group. The aromatic ring of the phenol is optionally substituted. The ether oxygen and the hydroxyl group are preferably separated by a C2-C4 alkylene group, preferably an ethylene group. Phenoxyethanol is the most preferred phenol ether alcohol.

[0042] The preferred hydroxyacetophenone is p-hydroxyacetophenone.

[0043] The aliphatic diol is an alkane having two hydroxyl groups. These hydroxyl groups are preferably linear or branched C2-C 10 Separated by alkylene groups

[0044] Preferred hydroxamic acids are saturated C3-C 12 Hydroxamic acids of alkanoic acids. A preferred hydroxamic acid is N-hydroxyoctanamide (=caprylhydroxamic acid).

[0045] Preferably, the antimicrobial agent is selected from the group consisting of hexylglycerin, ethylhexylglycerin or caprylic glycerin, sodium benzoate, benzyl alcohol, phenoxyethanol and N-hydroxyoctanamide.

[0046] More preferably, the antimicrobial agent is selected from the group consisting of hexylglycerin, ethylhexylglycerin or capric glycerin and N-hydroxyoctanamide.

[0047] Most preferably, the antimicrobial agent is hexylglycerin or ethylhexylglycerin.

[0048] In a preferred embodiment, the composition is a cosmetic composition.

[0049] The amount of 1,3-propanediol and / or N-hydroxyoctanamide is preferably 0.01 to 6.0% by weight, more preferably 0.05 to 5.0% by weight, and even more preferably 0.1 to 3.0% by weight, based on the total weight of the cosmetic composition.

[0050] The amount of the hyperbranched copolymer (HBC) in the cosmetic composition is usually 0.005 to 5.0% by weight, preferably 0.05 to 5.0% by weight, more preferably 0.1 to 3.0% by weight, and most preferably 0.5 to 2.5% by weight, based on the total weight of the cosmetic composition.

[0051] The cosmetic composition further preferably further comprises at least one emulsifier, preferably an anionic emulsifier, preferably an anionic emulsifier selected from the group consisting of potassium cetyl phosphate, disodium cetearyl sulfosuccinate, sodium stearoyl glutamate, sodium stearoyl lactylate, glyceryl stearate citrate and sodium cocoyl isethionate.

[0052] Potassium cetyl phosphate is commercially available as Amphisol® K from DSM Nutritional Products Ltd Kaiseraugst.

[0053] The amount of emulsifier is preferably in the range of 0.1 to 6.0% by weight, more preferably 0.25 to 5.0% by weight, and especially 0.5 to 4.0% by weight, relative to the total weight of the cosmetic composition.

[0054] The composition preferably does not contain sulfates.

[0055] The cosmetic composition therefore preferably does not contain any sulfates, in particular from the group consisting of alkyl sulfates, alkyl ether sulfates, alkyl amido ether sulfates, alkyl aryl polyether sulfates and monoglyceride sulfates, and mixtures thereof.

[0056] In this document, the term "free", for example as used in "sulfate-free", is used to mean that the respective substance is present in an amount of less than 0.5% by weight, in particular less than 0.1% by weight, more particularly less than 0.05% by weight, based on the weight of the composition. Preferably, "free" means that the respective substance is completely absent from the composition.

[0057] The term "sulfate-free" as used herein means a compound having the formula: [ka] "A" is used to mean that the composition does not contain any anionic surfactant having an anionic end group of

[0058] The cosmetic composition preferably does not contain cationic emulsifiers.Typical examples of such cationic emulsifiers are isostearamidopropyl dimethylamine, stearalkonium chloride, stearamidoethyl diethylamine, behentrimonium methosulfate, behenoyl PG-trimonium chloride, cetrimonium bromide, behenamidopropyl dimethylamine behenate, brassicamidopropyl dimethylamine, stearamidopropyl dimethylamine stearate, cocamidopropyl PG-dimonium chloride, distearoyl ethyl hydroxyethyl monium methosulfate, dicocoyl ethyl hydroxyethyl monium methosulfate, distearo ... laurylethyldimonium chloride, shea butter amidopropyltrimonium chloride, behenamidopropyl dimethylamine, brassyl isoleucine esylate, acrylamidopropyltrimonium chloride / acrylates copolymer, linoleamidopropylethyldimonium ethosulfate (ester), dimethyl lauramine isostearate, isostearamidopropyl lauryl acetodimmonium chloride, especially behentrimonium chloride, distearyldimonium chloride, cetrimonium chloride, steartrimonium chloride, and palmitamidopropyltrimonium chloride.

[0059] The cosmetic composition may further include cosmetic carriers, excipients and diluents, as well as additives and active ingredients commonly used in the skin care industry suitable for use in the cosmetic composition of the present invention, including, but not limited to, those described in, for example, the International Cosmetic Ingredient Dictionary & Handbook by Personal Care Product Council (http: / / www.personalcarecouncil.org / ), accessible via the online INFO BASE (http: / / online.personalcarecouncil.org / jsp / Home.jsp).

[0060] Such possible ingredients of the cosmetic composition are especially those that enhance performance and / or consumer acceptability, such as preservatives, antioxidants, fatty substances / oils, thickeners, emollients, light screening agents, moisturizers, fragrances, co-surfactants, fillers, sequestering agents, cationic, nonionic or amphoteric polymers or mixtures thereof, acidifying or basifying agents, viscosity modifiers, and natural hair nutrients, such as plant, fruit extracts, sugar derivatives and / or amino acids or any other ingredients that are usually incorporated into cosmetic compositions. The necessary amounts of auxiliaries and additives can be easily selected by a person skilled in the art based on the desired product and are illustrated in the examples, without being limited thereto.

[0061] Further ingredients can be added to the oil phase, the water phase, or added separately, as appropriate.

[0062] In an advantageous embodiment, the composition according to the invention comprises from 50% to 99%, preferably from 60% to 98%, more preferably from 70% to 98%, for example in particular from 80% to 95%, of a carrier relative to the total weight of the cosmetic composition.

[0063] In a particularly advantageous embodiment, the carrier further comprises at least 40% by weight of water, more preferably at least 50% by weight, most preferably at least 55% by weight, for example in particular 55-90% by weight of water.

[0064] Furthermore, the cosmetic composition preferably comprises at least one UV filter. The UV filter may be a liquid or solid UV filter. The UV filter may be a UV-A or UV-B filter.

[0065] 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 the person skilled in the art and include in particular cinnamates, such as octyl methoxycinnamate (PARSOL® MCX) and isoamyl methoxycinnamate (NeoHeliopan® E1000), salicylates, such as homosalate (3,3,5 trimethylcyclohexyl 2-hydroxybenzoate, PARSOL® HMS) and ethylhexyl salicylate (also known as ethylhexyl salicylate, 2 ethylhexyl 2-hydroxybenzoate, PARSOL® EHS), such as octocrylene, acrylates such as acrylate (2-ethylhexyl 2-cyano-3,3-diphenylacrylate, PARSOL® 340) and ethyl 2-cyano-3,3 diphenylacrylate, in particular esters of benzalmalonic acid such as dialkyl benzalmalonates, for example di(2-ethylhexyl) 4-methoxybenzalmalonate and polysilicone 15 (PARSOL® SLX), dialkyl esters of naphthalates, for example diethylhexyl 2,6-naphthalate (Corapan® TQ), syringylidene malonates, for example diethylhexyl syringylidene malonate (Oxynex® ST liquid), and benzotriazolyl dodecyl p-cresol (Tinoguard® TL) as well as benzophenone-3 and drometrizole trisiloxane.

[0066] Particularly advantageous liquid UV filters are octyl methoxycinnamate, homosalate, ethylhexyl salicylate, octocrylene, diethylhexyl 2,6-naphthalate, diethylhexyl syringylidene malonate, benzotriazolyl dodecyl p-cresol, benzophenone-3, drometrizole trisiloxane, polysilicone-15 and mixtures thereof.

[0067] 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 UV filters from 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.

[0068] The amount of each organic UV filter is preferably in the range of from 0.1 to about 6% by weight, preferably in the range of from 0.5 to 5% by weight, most preferably in the range of from 1 to 4% by weight, relative to the total weight of the cosmetic composition.

[0069] In the case of sun care compositions, the total amount of organic UV filters strongly depends on the targeted UV protection of the composition and usually ranges from 1 to 50% by weight, preferably from 5 to 40% by weight, relative to the total weight of the composition.

[0070] A sunscreen cream with SPF15 (SPF=sun protection factor) contains, for example, organic UV filters in a total amount of 4 to 20% by weight, more preferably 7 to 15% by weight, based on the total weight of the composition.

[0071] A sunscreen cream with SPF 30 contains, for example, organic UV filters in a total amount of 10 to 40% by weight, more preferably 15 to 25% by weight, based on the total weight of the composition.

[0072] A sunscreen cream with SPF50 contains, for example, organic UV filters in a total amount of 15 to 50% by weight, more preferably 20 to 40% by weight, based on the total weight of the composition.

[0073] Particularly suitable thickeners in all embodiments of the invention are xanthan gum, gellan gum and / or carboxymethylcellulose. Most preferably in all embodiments of the invention the thickener is xanthan gum or gellan gum. Further suitable thickeners are polyacrylates such as those commercially available under the trade name Carbomer, or acrylate / C10-30 alkyl acrylate crosspolymers or salts of polyacrylic acid, or polyacrylamides.

[0074] Such thickeners are used in an amount (total amount) selected from the range of preferably 0.1 to 1% by weight, more preferably 0.1 to 0.5% by weight, based on the total weight of the cosmetic composition.

[0075] It is preferred that the composition does not contain polyvinylpyrrolidone (PVP), and in particular does not contain alkylated polyvinylpyrrolidone, such as the copolymers of N-vinylpyrrolidone with hexadecane or eicosene, commercially available, for example, as Antaron V-216 or Antaron V-220.

[0076] Cosmetic compositions according to the present invention generally have a pH in the range of 3 to 10, preferably a pH in the range of 4 to 8, and most preferably a pH in the range of 4 to 7.5. The pH is adjusted by methods known to those skilled in the art using acids, such as hydroxy acids, including, for example, glycolic acid, lactic acid, malic acid, citric acid and tartaric acid, or bases, such as, for example, sodium hydroxide or potassium hydroxide, or ammonium hydroxide, and mixtures thereof.

[0077] Preferably, in the composition according to the invention, citric acid is used for pH adjustment in an amount of at least 0.0001% by weight, for example in an amount of 0.01 to 1% by weight, in particular in an amount of 0.01 to 0.5% by weight.

[0078] The cosmetic composition is preferably sulfate-free and / or paraben-free and / or silicone oil and / or silicone surfactant and / or methylisothiazolidine-free and / or polyvinylpyrrolidone (PVP), in particular alkylated polyvinylpyrrolidone-free.

[0079] The cosmetic composition is preferably a topical composition.

[0080] The term "topical" as used herein is understood herein to mean external application, in particular to keratinous materials, such as the skin, scalp, eyelashes, eyebrows, nails, mucous membranes and hair, preferably the skin.

[0081] Since the topical composition is intended for topical application, it is fully understood that the composition comprises a physiologically acceptable medium, i.e. a medium that is compatible with the skin, mucous membranes, and keratinous materials such as keratinous fibers. In particular, a physiologically acceptable medium is a cosmetically acceptable carrier.

[0082] The term "cosmetically acceptable carrier" means all carriers and / or excipients and / or diluents conventionally used in cosmetic compositions, in particular in sun protection products and the like.

[0083] Preferably, the cosmetic composition is a skin care composition.

[0084] In a further embodiment, the cosmetic composition is a decorative preparation or a functional preparation.

[0085] Examples of skin care compositions are, in particular, photoprotective compositions, anti-aging compositions, compositions / formulations for the treatment of photoaging, body oils, body lotions, body gels, treatment creams, skin protective ointments, skin powders, moisturizing gels, moisturizing sprays, facial and / or body moisturizers, skin tanning formulations (i.e. compositions for artificial / sunless tanning and / or browning of human skin), such as self-tanning creams, and skin whitening compositions.

[0086] Examples of functional formulations are cosmetic compositions containing active ingredients such as, but not limited to, hormone formulations, vitamin formulations, vegetable extract formulations, anti-aging formulations, and / or antimicrobial (antibacterial or antifungal) formulations.

[0087] The cosmetic composition is preferably a skin care composition.

[0088] In certain embodiments, the cosmetic composition is a UV care composition.The UV care composition is a photoprotective composition (UV care product), such as sunscreen milk, sunscreen lotion, sunscreen cream, sunscreen oil, sunblock or day care cream with SPF (sun protection factor).Sunscreen cream, sunscreen lotion, sunscreen milk and sunscreen composition are of particular interest.

[0089] The cosmetic composition according to the invention may take the form of a suspension or dispersion in a solvent or fatty substance or alternatively it may take the form of an emulsion or microemulsion (in particular of the oil-in-water type (O / W) or water-in-oil type (W / O), silicone-in-water type (Si / W) or water-in-silicone type (W / Si), PIT-emulsion, multiple emulsion (for example of the oil-in-water-in-oil type (O / W / O) or water-in-oil-in-water type (W / O / W)) or Pickering emulsion, hydrogel, alcohol gel, lipogel, single- or multiphase solution or vesicle dispersion, or other usual forms which can also be applied by pen, as a mask or as a spray.

[0090] Preferred cosmetic compositions in all embodiments of the present invention are emulsions containing an oil phase and an aqueous phase, such as in particular O / W, W / O, Si / W, W / Si, O / W / O, W / O / W multiple or Pickering emulsions.

[0091] The total amount of oil phase present in such an emulsion is preferably at least 10% by weight, for example in the range of 10 to 60% by weight, preferably in the range of 15 to 50% by weight, most preferably in the range of 15 to 40% by weight, relative to the total weight of the cosmetic composition.

[0092] The amount of aqueous phase present in such emulsions is preferably at least 20% by weight, for example in the range of 40 to 90% by weight, preferably in the range of 50 to 85% by weight, most preferably in the range of 60 to 85% by weight, relative to the total weight of the cosmetic composition.

[0093] The cosmetic composition may take the form of a liquid, a lotion, a thickened lotion, a gel, a cream, a milk, an ointment or a paste.

[0094] More preferably, the cosmetic composition according to the invention takes the form of an oil-in-water (O / W) emulsion, comprising an oily phase dispersed in an aqueous phase in the presence of an O / W or Si / W emulsifier, the preparation of such O / W emulsions being well known to those skilled in the art.

[0095] The composition in the form of an O / W emulsion according to the invention can be provided, for example, in all formulation forms of O / W emulsions, for example in the form of serums, milks or creams, and is produced according to the usual methods. The composition that is the subject of the present invention is preferably intended for topical application and may in particular constitute a dermatological or cosmetic composition, for example intended to protect human skin against the harmful effects of ultraviolet radiation (anti-wrinkle, anti-aging, moisturizing, anti-sunburn, etc.).

[0096] Preferably, the cosmetic composition is a shampoo or a hair conditioner.

[0097] Preferably, the cosmetic composition is a hair care composition.

[0098] Preferably, the cosmetic composition is a shampoo or a hair conditioner.

[0099] More preferably, the cosmetic composition is a topical composition applied to human skin, scalp and / or hair.

[0100] Surprisingly, it has been found that highly branched copolymers (HBCs) enhance the antimicrobial activity of antimicrobial agents in cosmetic compositions.

[0101] Thus, a further aspect of the present invention provides the use of the following monomers to enhance the antimicrobial activity of 1,3-propanediol and / or N-hydroxyoctanamide: (i) dodecenylsuccinic anhydride; (ii) diisopropanolamine; (iii) Bis-dimethylaminopropylamine A highly branched copolymer (HBC) of the formula: [ka] and having a molecular weight Mn of 1200 to 4000 g / mol.

[0102] The antibacterial activity was confirmed especially against microorganisms selected from the group consisting of Kocuria rhizophila, Staphylococcus aureus, Enterobacter gergoviae, Escherichia coli, Pseudomonas aeruginosa, Pseudomonas fluorescens, Pseudomonas putida, Aspergillus brasiliensis, Penicillium pinophilum and Candida albicans, in particular against Escherichia coli.

[0103] The use of hyperbranched copolymers (HBC) to enhance the antimicrobial action of 1,3-propanediol and / or N-hydroxyoctanamide can be done both in a cosmetic sense as well as in a pharmaceutical sense.

[0104] Preferably the use is a non-therapeutic use.

[0105] In cosmetic compositions, the non-therapeutic use is preferably a cosmetic use, such as for maintaining skin homeostasis and / or balancing the skin microbiome and / or hair microbiome.

[0106] It has been confirmed that the antibacterial effect is significantly increased when the hyper-branched copolymer (HBC) is added to a cosmetic composition containing 1,3-propanediol and / or N-hydroxyoctanamide. In other words, by further adding the hyper-branched copolymer (HBC) to a cosmetic composition containing 1,3-propanediol and / or N-hydroxyoctanamide, the number of confirmed microorganisms is lower than when the hyper-branched copolymer (HBC) is not used. The hyper-branched copolymer (HBC) has a synergistic effect on the antibacterial effect of 1,3-propanediol and / or N-hydroxyoctanamide in the composition, particularly in the cosmetic composition.

[0107] This is also highly advantageous in that the amount of 1,3-propanediol and / or N-hydroxyoctanamide can be reduced by adding an effective amount of the hyperbranched copolymer (HBC) described above to maintain the same antimicrobial activity.

[0108] It has further been found that the antimicrobial effect is particularly pronounced in the aqueous phase, which is highly advantageous since it is known that it is usually the aqueous phase of a product that is most susceptible to microbial growth.

[0109] [Example] The present invention is further illustrated by the following experiments. These examples are merely illustrative and are not intended to limit the scope of the invention in any way.

[0110] [Production of hyperbranched copolymer (HBC1)] A hyperbranched copolymer HBC1 of the monomers dodecenylsuccinic anhydride and diisopropanolamine and bis-dimethylaminopropylamine was prepared according to Example 3 of EP 2794729 B1 using 237.59 g N,N-bis(N'N'-dimethylaminopropyl)amine, 112.6 g diisopropanolamine and 426.89 g dodecenylsuccinic anhydride. After heating and vacuum, a residual carboxylic acid content <0.3 meq / g (titration analysis) AV=9.8 mg KOH / g and an amine content of 2.99 meq / g (titration analysis) and a molecular weight Mn=2240 Da were obtained. 1 H-NMR analysis revealed the following formula: [ka] This product was reacted with sodium chloroacetate in water and stirred at 80° C. until complete conversion of the chloroacetate was indicated, giving a hyperbranched copolymer HBC1 with end groups of 1.0 and a molecular weight Mn of 2.3 kDa.

[0111] The hyperbranched copolymer HBC1 was used as a 50% solution in water in the following experiments, the amounts given in Table 1 are relative to the amount of polymer.

[0112] [Antibacterial activity test (24-hour challenge test)] Since it is known that the aqueous phase of the product is usually the most susceptible to microbial growth, the antimicrobial effectiveness was evaluated similar to the regulatory preservative efficacy test method for aqueous solutions (NF EN ISO 11930).

[0113] Therefore, solutions of HPC1 and / or 1,3-propanediol and / or N-hydroxyoctanamide were prepared under sterile conditions in the amounts indicated in Table 1. For this, they were solubilized in physiological serum containing 0.85% by weight NaCl. The solutions were placed in 96 deep-well plates (1.6 ml / well). The incubation time was 6.3 to 10 min for Escherichia coli or Aspergillus brasiliensis, respectively. *10 5 or 4.5 * 10 4 Wells were contaminated at 0.01 cfu / ml. After contamination, each well was mixed thoroughly to ensure uniform distribution of the microorganisms. Each plate was then incubated for 24 hours at 22° C. 24 hours after contamination, a count of the (remaining) population was performed and reported in Table 1.

[0114] [Table 1]

[0115] The results in Table 1 clearly show that these particular copolymers, i.e., hyperbranched copolymers, increase the antibacterial activity of 1,3-propanediol and / or N-hydroxyoctanamide. This effect is synergistic. It has been confirmed that HPC1 and 1,3-propanediol and / or N-hydroxyoctanamide, especially in combination with N-hydroxyoctanamide, show increased antibacterial activity in various cosmetic compositions, such as shampoos or o / w skin care emulsions.

Claims

1. a) the following monomers: (i) dodecenylsuccinic anhydride; (ii) diisopropanolamine; (iii) Bis-dimethylaminopropylamine A hyperbranched copolymer (HBC) of the formula: 【Chemistry 1】 and a molecular weight Mn of 1200 to 4000 g / mol, b) 1,3-propanediol and / or N-hydroxyoctanamide; A composition comprising:

2. The hyperbranched copolymer (HBC) is prepared by the following successive steps: a1) polymerizing monomer (i), monomer (ii) and monomer (iii) to form a copolymer having the following formula: 【Chemistry 2】 obtaining a polyesteramide having dimethylamino end groups of a2) quaternization of the dimethylamino groups of the polyesteramide of step a1) with 2-chloroacetate; The composition according to claim 1, characterized in that it is produced by

3. 3. The composition according to claim 1, wherein the molar ratio of monomer (i):monomer (ii) is from 5:1 to 0.5:

1.

4. The composition according to any one of claims 1 to 3, characterized in that the molar ratio of monomer (i):monomer (iii) is from 5:1 to 0.5:

1.

5. The hyperbranched copolymer has a number average molecular weight M ｎ 5. The composition according to claim 1, characterized in that it has a molecular weight of from 1400 to 3000 g / mol.

6. A composition according to any one of claims 1 to 5, characterized in that the hyperbranched copolymer is Polyquaternium-110.

7. 7. The composition according to claim 1, wherein the weight ratio of the hyperbranched copolymer (HBC) to 1,3-propanediol and / or N-hydroxyoctanamide is from 1:30 to 30:

1.

8. The composition according to any one of claims 1 to 7, characterized in that it is a cosmetic composition.

9. A cosmetic composition according to claim 8, characterized in that the amount of said hyperbranched copolymer (HBC) ranges from 0.005 to 5.0% by weight, relative to the total weight of said cosmetic composition.

10. A cosmetic composition according to claim 8 or 9, characterized in that it is a skin care composition.

11. A cosmetic composition according to claim 8 or 9, characterized in that it is a hair care composition.

12. A cosmetic composition according to any one of claims 8 to 11, characterized in that it is a shampoo or a hair conditioner.

13. A cosmetic composition according to any one of claims 8 to 11, characterized in that it is a topical composition applied to human skin, scalp and / or hair.

14. The following monomers to enhance the antimicrobial activity of 1,3-propanediol and / or N-hydroxyoctanamide: (i) dodecenylsuccinic anhydride; (ii) diisopropanolamine; (iii) Bis-dimethylaminopropylamine A hyperbranched copolymer (HBC) of the formula: 【Chemistry 3】 and having a molecular weight Mn of 1200 to 4000 g / mol.

15. 15. Use according to claim 14, characterized in that said use is a cosmetic use.

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