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WO2025011747A1 - 3-hydroxypropylesters utilisés comme agents modulant la qualité de mousse et la viscosité dans des formulations contenant un tensioactif - Google Patents

3-hydroxypropylesters utilisés comme agents modulant la qualité de mousse et la viscosité dans des formulations contenant un tensioactif Download PDF

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Publication number
WO2025011747A1
WO2025011747A1 PCT/EP2023/069029 EP2023069029W WO2025011747A1 WO 2025011747 A1 WO2025011747 A1 WO 2025011747A1 EP 2023069029 W EP2023069029 W EP 2023069029W WO 2025011747 A1 WO2025011747 A1 WO 2025011747A1
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WIPO (PCT)
Prior art keywords
sodium
betaine
formulation
surfactant
glucoside
Prior art date
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PCT/EP2023/069029
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English (en)
Inventor
Sabine Lange
Ricarda KRÄLING
Steffen NORDZIEKE
Christin KOCH
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Symrise AG
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Symrise AG
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Publication date
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Priority to PCT/EP2023/069029 priority Critical patent/WO2025011747A1/fr
Publication of WO2025011747A1 publication Critical patent/WO2025011747A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active compounds

Definitions

  • the present invention primarily relates to compounds of formula (I) as disclosed herein and their use for modifying the viscosity of a surfactant containing formulation and/or for modifying the foam quality of the same.
  • viscosity is an important factor for it to be a functional product. Viscosity influences the cleansing efficiency, users’ perception, foaming properties, production filling, packaging, storage, and long-term stability. For instance, to meet customers’ expectations the liquid should be easily applicable to the skin while still adding a “rich” feeling. Liquids which are considered “rich” usually have a higher viscosity. Moreover, in order to improve the long-term stability during storage the viscosity of the liquid should be as high as possible, since the higher the viscosity is the lower the sedimentation of dispersed particles will be. Generally, water-soluble polymers such as polyquaternium 10 act as viscosity modifiers (i.e. thickening agent) to increase the viscosity.
  • Sodium chloride can be used to thicken anionic surfactant-based formula.
  • Surfactants form the core of all shampoo formulations, and contribute to a wide range of different benefits, including cleansing, foaming, rheology control, skin mildness and the deposition of benefit agents to the hair and scalp.
  • Surfactants traditionally used in the cosmetic industry are sulfates such as sodium laureth sulfate, sodium lauryl sulfate and ammonium laureth sulfate. While being effective in terms of cleansing and rheology control, they are considered problematic for the protective lipid layer of the skin. As a consequence, sulfate-free products have been developed.
  • a disadvantage of sulfate-free products is that their viscosity is more difficult to set as they cannot be thickened with sodium chloride, and that they tend to have poorer foaming properties.
  • the viscosity can be increased by using more polymers in sulfate free formulations, however, this is on cost of the foaming properties.
  • Surfactant based formulations not only form the core of shampoo products; also other personal care products, e.g., skin cleansing products, or household products, e.g., dish washing products or surface cleaners, are surfactant based. It was thus an object of the present invention to provide surfactant-based formulations whose viscosity can be easily set within the range desirably for personal care and household products.
  • a first aspect of the present invention pertains to the use of at least one of compounds of formula (I) for modifying the viscosity and/or for modifying the foam quality of a surfactant containing formulation.
  • the compounds of formula (I) as described herein are defined as follows: wherein R is selected from the group consisting of: ! n-nonyl, !
  • n-undecyl That is, the compounds encompassed by the above definition are 3- hydroxypropyldecanoate when R is n-nonyl and 3-hydroxypropyldodecanoate (when R is n-undecyl. 3-hydroxypropyldecanoate and 3-hydroxypropyldodecanoate have the structures of formula (1-a) and formula (1-b), respectively: .
  • a method of modifying the viscosity and/or of modifying the foam quality of a surfactant containing formulation comprises or consists of the following steps: (a) providing at least one of compounds of formula (I) as defined herein (b) providing a surfactant containing base formulation, and (c) mixing the compound(s) of step (a) with the base formulation of step (b) in an amount sufficient to reach a predetermined viscosity and/or foam quality.
  • the property of the herein described compounds of formula (I) characterized by the term “modifying the viscosity” can be determined by measuring the viscosity of a surfactant- based formulation containing at least one of the compounds of formula (I) as compared to a corresponding surfactant-based formulation lacking the at least one of the compounds of formula (I).
  • the phrase “modifying the viscosity” is preferably an increase of the viscosity obtained by adding at least one of the compounds of formula (I) to a surfactant containing base formulation, i.e. a base formulation containing at least one surfactant, as compared to the surfactant containing base formulation to which not the at least one of the compounds of formula (I) was added.
  • the viscosity is determined using a Thermo Scientific Haake RheoStress1 device with the following parameters Geometry: C60/1° Ti L; temperature 23°C; shear frequency 10 s -1 .
  • the property characterized by the expression “modifying the foam quality” can be determined by measuring the foam quality of a surfactant-based formulation containing at least one of the compounds of formula (I) as compared to a corresponding surfactant based formulation lacking the at least one of the compounds of formula (I).
  • the phrase “modifying the foam quality” is preferably one or more of a decrease of foam droplet size, thicker foam perception and creamier foam perception, obtained by adding at least one of the compounds of formula (I) to a surfactant containing base formulation as compared to the surfactant containing base formulation to which not the at least one of the compounds of formula (I) was added.
  • the foam can be evaluated in accordance with the methods given in the example section.
  • a surfactant-based formulation forms a further aspect of the present invention.
  • the surfactant-based formulation comprises the following constituents: (i) at least one of compounds of formula (I) as defined herein, and (ii) at least one surfactant.
  • a ”surfactant based formulation” is a formulation that contains a surfactant, i.e. at least one surfactant.
  • Surfactants are an amphiphilic class of molecules, having both a hydrophilic and a hydrophobic part. The nature of the hydrophilic moiety is commonly used to classify surfactants in four basic categories: anionic, cationic, amphoteric and non-ionic. This class of chemicals has an ability to modify the properties of a surface and an interface.
  • surfactants can perform diverse functions including: cleaning, wetting, emulsification, solubilization, dispersion, foaming, penetration enhancement and antimicrobial activity. Due to this functional diversity, surfactants may be applied in production and processing of foods, agrochemicals, pharmaceuticals, personal care and laundry products, petroleum, mineral oils, lubricants, and paints. In cosmetic products surfactants may serve as detergents (cleansing agents), emulsifiers, wetting or foaming agents, opacifiers, thickening agents, foam depressors, hair conditioners and antistatic agents.
  • base formulation as used herein means an intermediate product that does not include all ingredients of the final formulation, and in particular does not include a compound of formula (I).
  • an amount sufficient to reach a predetermined viscosity and/or foam quality denotes an amount of the compound of formula (I) that provides a tangible modification of the viscosity and/or of the foam quality.
  • the expression means that a tangible viscosity increase of the surfactant based formulation containing the compound of formula (I) can be observed as compared to a corresponding surfactant based formulation lacking the compound of formula (I).
  • the herein disclosed 3-hydroxypropoyl esters are capable of imparting a personal care or household formulation, in particular a shampoo or a hand dishwashing detergent formulation, with a desirable property profile including, but not limited to, a thicker and creamier appearance.
  • the formulation is a personal care or a household formulation.
  • the formulation is selected from the group consisting of formulations of shampoos, conditioners, hair styling, intimate gels, concentrates, solid formulations, micellar waters, hand dishwashing detergents, auto dishwashing detergents, all purpose cleaners, floor cleaners, kitchen cleaners.
  • Preferred formulations include a surfactant system.
  • a surfactant system refers to a combination of two or more different surfactants.
  • the surfactant system preferably comprises: ! at least one anionic surfactant and/or at least one nonionic surfactant; and ! optionally, at least one surfactant selected from the group consisting of amphoteric, zwitterionic and cationic surfactants.
  • the surfactant system is free of sulfate containing surfactants.
  • formulations being sulfate-free. Sulfates are a type of surfactant, which when combining with water, lather into a rich, foamy substance.
  • the surfactant may be a biosurfactant, i.e. of microbial origin or prepared or derived from biobased starting materials comprising only non-fossil fuel-based carbon. Assessment of the biobased carbon in a material can be performed as further described below.
  • Preferred surfactant(s) include the following: If an anionic surfactant (A) is present, it is preferably selected from the groups A-1 to A-5: (A-1) Acylamino acids (and their salts), such as ! acylglutamates, for example sodium acylglutamate, di-TEA- palmitoylaspartate and sodium caprylic / capric glutamate, ! acyl peptides, for example palmitoyl-hydrolyzed milk protein, sodium cocoyl- hydrolysed soy protein and sodium / potassium cocoyl-hydrolyzed collagen, !
  • sarcosinates for example myristoyl sarcosine, TEA-lauroyl sarcosinate, sodium lauroyl sarcosinate and sodium cocoyl sarcosinate, ! taurates, for example sodium lauroyl taurate and sodium methyl cocoyl taurate, ! acyl lactylates, lauroyl lactylate, caproyl lactylate, ! alaninates;
  • A-2 Carboxylic acids and derivatives, such as ! carboxylic acids, for example lauric acid, aluminum stearate, magnesium alkoxide and zinc undecylenate, !
  • ester carboxylic acids for example calcium stearoyl lactylate, laureth-6-citrate and sodium PEG-4-lauramide carboxylate, ! Ether carboxylic acids, for example sodium laureth-13-carboxylate and sodium PEG-6-cocamide carboxylate;
  • Phosphoric acid esters and salts such as DEA-oleth-10-phosphate and dilaureth-4- phosphate;
  • alkyl sulfonates for example sodium coconut monoglyceride sulfate, sodium CM-U olefin sulfonate, ⁇ -olefin sulfonate like C14-16 olefin sulfonate,e sodium lauryl sulfoacetate and magnesium PEG-3 cocamide sulfate,sulfosuccinates, for example dioctyl sodium sulfosuccinate, disodium laureth sulfosuccinate, Dinatrium laurylsulfosuccinat and disodium undecylenamido MEA sulfosuccinate; (A-5) Sulfuric acid esters, such as !
  • alkyl ether sulfate for example sodium, ammonium, magnesium, MIPA, TIPA- laureth sulfate, sodium myreth sulfate and sodium C 12-13 -parethsulfate, ! alkyl sulfates, for example sodium, ammonium and TEA lauryl sulfate.
  • an amphoteric surfactant (B) is present, it is preferably selected from the groups B-1 to B-3: (B-1) Cocamidopropyl betaine, (B-2) Acyl / dialkylethylenediamine, for example sodium acylamphoacetate, disodium acyl amphodipropionate, dinatnumalkylamphodiacetat, sodium acylamphohydroxypropylsulphonate, disodium acylamphodiacetate and sodium acylamphopropionate, (B-3) N-alkylamino acids, for example aminopropylalkylglutamide, alkylaminopropionic acid, sodium alkylimidodipropionate and lauroamphocarboxyglycinate.
  • B-1 to B-3 (B-1) Cocamidopropyl betaine, (B-2) Acyl / dialkylethylenediamine, for example sodium acylamphoacetate, disodium acyl amphodipropionate, dinat
  • a non-ionic surfactant (C) is present, it is preferably selected from the groups C-1 to C-9: (C-1) Alcohols, (C-2) alkanolamides, such as cocamide MEA / DEA / MIPA, (C-3) amine oxides, such as cocoamidopropylamine oxide, (C-4) esters formed by esterification of carboxylic acids with ethylene oxide, glycerol, sorbitan or other alcohols, (C-5) ethers, for example ethoxylated / propoxylated alcohols, ethoxylated / propoxylated esters, ethoxylated / propoxylated glycerol esters, ethoxylated / propoxylated cholesterols, ethoxylated / propoxylated triglyceride esters, ethoxylated propoxylated lanolin, ethoxylated / propoxylated polysiloxanes, propoxylated PO
  • a cationic surfactant (D) is present, it is preferably selected from the group consisting of benzyl dimethylstearyl ammonium chloride, cetrimonium chloride, trimethyl ammonium chloride or bromide, lauryl or cetyl pyridinium chloride, alkyl dimethyl amine oxides or alkyl aminoethyl dimethyl amine oxides, benzalkonium chloride, polyquaternium-6, polyquaternium-7, polyquaternium-10, polyquaternium-22, polyquaternium-37, cocamide MEA, guar hydroxypropyltrimonium chloride, If a sulfate-free surfactant system (E) is present, one, several or all surfactants in the sulfate-free surfactant system is/are preferably selected from the group consisting of dimethyl lauramide/myristamide, cetyl betaine, lauramidopropyl betaine, cocamidopropyl betaine, coco-betaine, almond
  • the surfactant system comprises one or more of sodium laureth sulfate, lauryl glycoside, cocoamidopropyl betaine and polyquaternium-10.
  • the formulation comprises the at least one compound of formula (I) in an amount of 0.01 to 10 wt.-%, preferably 0.05 to 2.5 wt.-%, more preferably 0.1 to 1.0 wt.-%, based on the total weight of the formulation. In this range, a profound viscosity increase is observed.
  • the viscosity increase may be at least 50%, at least 100%, at least 150%, at least 200%, at least 250%, at least 300%, at least 350%, at least 400%, at least 450%, at least 500%, or even more than 500%.
  • the formulation comprises 5 to 90 wt.-%, preferably 10 to 80 wt.-% of the at least one surfactant, based on the total weight of the formulation.
  • Preferred formulations further comprise at least one linear alkanediol having a carbon chain of 5 to 12 carbon atoms.
  • the linear alkanediol is a 1,2-alkanediol, a 2,3-alkanediol, a 3,4-alkanediol, a 1,3-alkanediol, or a mixture thereof, more preferred a 2,3-alkanediol or a 1,3-alkanediol.
  • linear alkanediols are selected from the group of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-undecanediol and 1,2-dodecanediol. While linear alkanediols are variously used in the art due to their advantageous property profile, they also tend to be disadvantageous because of their viscosity reducing effect.
  • compositions comprise the at least one compound of formula (I) and the at least one surfactant in a weight ratio of 0.0005:1 to 2:1, preferably 0.001:1 to 1:1, more preferably 0.005:1 to 0.5:1, most preferably 0.01:1 to 0.1:1.
  • Optional constituents of formulations as described herein include on or more of the following: abrasives, anti-acne agents, agents against ageing of the skin, anti-cellulitis agents, anti-dandruff agents, anti-inflammatory agents, anti-microbial agents, irritation- preventing agents, irritation-inhibiting agents, antioxidants, astringents, odor absorbers, perspiration-inhibiting agents, antiseptic agents, anti-statics, binders, buffers, carrier materials, chelating agents, cell stimulants, cleansing agents, depilatory agents, surface- active substances, deodorizing agents, antiperspirants, softeners, emulsifiers, enzymes, enzyme inhibitors, essential oils, fibers, film-forming agents, fixatives, foam-forming agents, foam stabilizers, substances for preventing foaming, foam boosters, gelling agents, gel- forming agents, hair care agents, hair-setting agents, hair-straightening agents, moisture- donating agents, moisturizing substances, moisture-retaining substances, bleach
  • Preferred constituents of formulations as described herein include on or more of the following: agents against ageing of the skin, anti-microbial agents, antioxidants, chelating agents, emulsifiers, surfactants, preservatives, green and synthetic polymers, skin-cooling agents, rheology additives, oils, fragrances, perfume oils, and polyols.
  • Particular preferred constituents include at least one preservatives (different from the compounds of formula (I) and the surfactants as described herein). Examples of the aforementioned optional and preferred constituents as well as further constituents that can be included in the preparations as described herein can be found in paragraphs [0284] to [0351] of WO2022/122935.
  • the compounds of formula (I) are to be understood as preferred compounds of the present disclosure only, and the aspects, embodiments, features and effects described in conjunction with the compounds of formula (I) are to be understood to be correspondingly applicable to the compounds of formula (II).
  • X is as defined in formula (I), or that preferred preparations may comprise the compounds of formula (II) in the same amount as described for the compounds of formula (I).
  • R 1 is -OH
  • R 2 and the -OH group shown in formula (II) are joined together to form the following compound of formula (II-a): !
  • R 3 (as defined above) can be on any one of the free carbon atoms of the benzyl ring, i.e. X can be selected from the group consisting of: . Structures of particular interest are:
  • the compounds of formulae (I) are accessible not only via precursors of petrochemical origin, but advantageously also in a sustainable and/or cost-efficient way from biobased starting materials comprising only non-fossil fuel-based carbon.
  • Assessment of the biobased carbon in a material can be performed through standard test methods. Using radiocarbon and isotope ratio mass spectrometry analysis, the biobased content of materials can be determined. ASTM International, formally known as the American Society for Testing and Materials, has established a standard test method for assessing the biobased content of materials. The ASTM method is designated ASTM D6866.
  • more than 50% of the carbon atoms contained in a compound of formula (I) are biobased, based on the total number of carbon atoms contained in said compound of formula (I). More preferably, more than 60%, 70%, 75%, 80%, 85%, or 90% of the carbon atoms contained in a compound of formula (I) are biobased, based on the total number of carbon atoms contained in said compound of formula (I). The same is true for compounds of formula (II).
  • Fig.1 effect of 3-hydroxypropylester on the relative viscosity in sulfate containing shampoo formulations, as compared to corresponding formulation lacking the 3- hydroxypropylester (referred to as placebo).
  • Fig.2 effect of 3-hydroxypropylester on the relative viscosity in sulfate free shampoo formulations, as compared to corresponding formulation lacking the 3- hydroxypropylester (referred to as placebo).
  • Fig.2 shows that, also in sulfate-free shampoos, the tested 3-hydroxypropylester increased the relative viscosity several fold as compared to corresponding formulation lacking the 3- hydroxypropylester (referred to as placebo in Fig.2). By far the highest increase was seen with 1.0% 3-hydroxypropoyl dodecanoate. Also for sulfate-free shampoos, the foam quality of the shampoo (in terms of thickness and creaminess) is assumed to be enhanced as a result of addition of the tested 3- hydroxypropylesters. 4.
  • Formulation examples Formulation Anti Oil Shampoo Refreshing Green Body Jello Shampoo sulfate free Antidandruff Shampoo Shampoo Wild Berries shower Polish All Natural shower Jelly Aloe Shower Cream Fresh Hair shampoo Virgin Mojito Pre-Shampoo Hair conditioner with UV protection Detox Refreshing Spray for Hair Scalp soothing hair conditioner with UV-B/UV-A Conditioner protection, rinse off Refreshing conditioning Foam Hair Conditioner, leave on Hair Refreshener Mist H air Styling Hair styling gel Intimate Sensi-Gel Gel Mild femine wash Cleansing Micellar Gel Concentrates & Solid Hair Soap Shampoo Bar Formulations All in one Bar Shampoo body and beard Simple Hand dish wash liquid Dishwash liquid manual Antibacterial HDWL Homecare High performance HDWL with enzymes HDWL 1 HDWL 2 HDWL 3 Cosmetic formulations (compositions) - amounts are indicated as % by weight for all formulations.

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Abstract

La présente invention concerne principalement des composés de formule (I) et leur utilisation pour modifier la viscosité et/ou pour modifier la qualité de mousse d'une formulation contenant un tensioactif.
PCT/EP2023/069029 2023-07-10 2023-07-10 3-hydroxypropylesters utilisés comme agents modulant la qualité de mousse et la viscosité dans des formulations contenant un tensioactif Pending WO2025011747A1 (fr)

Priority Applications (1)

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PCT/EP2023/069029 WO2025011747A1 (fr) 2023-07-10 2023-07-10 3-hydroxypropylesters utilisés comme agents modulant la qualité de mousse et la viscosité dans des formulations contenant un tensioactif

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PCT/EP2023/069029 WO2025011747A1 (fr) 2023-07-10 2023-07-10 3-hydroxypropylesters utilisés comme agents modulant la qualité de mousse et la viscosité dans des formulations contenant un tensioactif

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020160905A1 (fr) * 2019-02-04 2020-08-13 Symrise Ag Activité antimicrobienne d'esters d'acides gras et combinaisons de ceux-ci
WO2020160904A1 (fr) * 2019-02-04 2020-08-13 Symrise Ag Agents actifs pour soins de la peau et des cheveux avec des propriétés de modification physico-chimique
WO2020160742A1 (fr) * 2019-02-04 2020-08-13 Symrise Ag Agents actifs pour le soin de la peau et des cheveux aux propriétés de modification sensorielle
WO2022122935A1 (fr) 2020-12-09 2022-06-16 Symrise Ag Compositions comprenant un ou plusieurs (bio)-alcanediols avec principes actifs

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020160905A1 (fr) * 2019-02-04 2020-08-13 Symrise Ag Activité antimicrobienne d'esters d'acides gras et combinaisons de ceux-ci
WO2020160904A1 (fr) * 2019-02-04 2020-08-13 Symrise Ag Agents actifs pour soins de la peau et des cheveux avec des propriétés de modification physico-chimique
WO2020160742A1 (fr) * 2019-02-04 2020-08-13 Symrise Ag Agents actifs pour le soin de la peau et des cheveux aux propriétés de modification sensorielle
WO2022122935A1 (fr) 2020-12-09 2022-06-16 Symrise Ag Compositions comprenant un ou plusieurs (bio)-alcanediols avec principes actifs

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