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EP3911296A1 - Diesters de 1,3-propanediol végétal - Google Patents

Diesters de 1,3-propanediol végétal

Info

Publication number
EP3911296A1
EP3911296A1 EP19701066.3A EP19701066A EP3911296A1 EP 3911296 A1 EP3911296 A1 EP 3911296A1 EP 19701066 A EP19701066 A EP 19701066A EP 3911296 A1 EP3911296 A1 EP 3911296A1
Authority
EP
European Patent Office
Prior art keywords
acid
oil
diesters
preparations
fatty acids
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19701066.3A
Other languages
German (de)
English (en)
Inventor
Martina König
Martina Issleib
Lars Jung
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Symrise AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Symrise AG filed Critical Symrise AG
Publication of EP3911296A1 publication Critical patent/EP3911296A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water 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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A61K2800/34—Free of silicones

Definitions

  • the invention is in the field of cosmetics and relates to new vegetable-based oil bodies with reduced stickiness and their use as a replacement for silicone compounds.
  • Cosmetic preparations contain properties to adjust certain product properties, e.g. UV protection, moisture, consistency and the like special active ingredients and additives such as UV filters, oil bodies or thickeners, which, however, when applied to the skin, quickly make them feel dull, heavy and, above all, sticky, which is why such products are quickly assessed by consumers as inferior.
  • product properties e.g. UV protection, moisture, consistency and the like special active ingredients and additives such as UV filters, oil bodies or thickeners, which, however, when applied to the skin, quickly make them feel dull, heavy and, above all, sticky, which is why such products are quickly assessed by consumers as inferior.
  • EP 0914087 Bl (COGNIS) are special fat components, which are also used as a substitute for silicone oils in hair care products; Ester oils are not mentioned.
  • EP 1853219 Al (COGNIS) describes the use of branched-chain oil bodies; linear structures are not mentioned.
  • the object of the present invention was therefore to provide alternative oil bodies that are suitable as a replacement for silicone compounds in general and cyclic silicones in particular and, above all, are easy to distribute, spread quickly and are neither heavy nor sticky feel on the skin. Furthermore, it should be emphasized that the substitutes are accessible from renewable, especially vegetable sources.
  • a first object of the invention relates to diesters of 1,3-propanediol with linear fatty acids having 6 to 22 carbon atoms and 0 or 1 to 3 double bonds with the proviso that both the 1,3-propanediol and the fatty acids exclusively from vegetable sources.
  • the diesters according to the invention not only have an overall performance spectrum that corresponds to the task, but it was particularly surprising that the raw material base also has an influence on the sensory properties of the 1,3-propanediol used Has esterification product.
  • the product 1,3-propanediol dicaprylate / caprate which is particularly preferred according to the invention, has a demonstrably lower stickiness if the diol component has been produced on a vegetable basis instead of on a petrochemical basis. The cause of this has not yet been fully determined, but it appears that certain by-products that are present in the petrochemical-based 1,3-propanediol are adversely affecting its application properties.
  • the diesters according to the invention are derived from 1,3-propanediol and corresponding linear, saturated or unsaturated fatty acids having 6 to 22 and in particular 8 to 12 carbon atoms and 0 and / or 1 to 3 double bonds.
  • pure fatty acids are generally not used, but technical mixtures or fractions.
  • Saturated fatty acids with 6 to 10 carbon atoms are preferably used.
  • Saturated fatty acids such as caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidonic acid and behenic acid as well as the unsaturated fatty acids palmoleic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, gadoleic acid and erucic acid are generally suitable.
  • technical mixtures can be used, such as palm oil fatty acid or coconut fatty acid. All of these fatty acids are required to be of vegetable origin, ie they are pro- Products obtained by saponification of oils such as palm oil, coconut oil, palm kernel oil, olive oil, sunflower oil and the like.
  • 1,3-propanediol also comes from vegetable sources.
  • the usual production of 1,3-propanediol is based on petrochemical raw materials, such as ethylene oxide, which is first hydroformylated. The aldehyde obtained as intermediate is then hydrogenated to the diol.
  • Corresponding products that are manufactured, for example, on the basis of corn can be found on the market, for example, under the name ZEM EA from DuPont.
  • Another object of the invention relates to cosmetic preparations containing the diesters according to the invention, preferably in amounts of about 0.1 to about 50% by weight, in particular about 1 to about 30% by weight, particularly preferably about 2 to about 25% by weight and most preferably about 3 to about 15% by weight.
  • the preparations are preferably skin care products or sun care products, which can be present as W / O or O / W emulsions. These preparations are preferably free of silicone compounds. “Free” in this context is to be understood to mean that the content of silicone compounds is less than 1% by weight, based on the preparations.
  • the agents according to the invention can contain further typical auxiliaries and additives, such as, for example, mild surfactants, oil bodies, emulsifiers, pearlescent waxes, consistency agents, thickeners, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, UV -Light protection filter, pigments, moisturizing agents, biogenic agents, antioxidants, deodorants, antiperspirants, anti-dandruff agents, film formers, swelling agents, insect repellents, self-tanners, tyrosine inhibitors (depigmenting agents), hydrotropes, solubilizers, preservatives and perfume oils, colorants.
  • auxiliaries and additives such as, for example, mild surfactants, oil bodies, emulsifiers, pearlescent waxes, consistency agents, thickeners, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids,
  • Anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants may be present as surface-active substances, their proportion of the agents usually being about 1 to 70, preferably 5 to 50 and in particular 10 to 30% by weight wearing.
  • anionic surfactants are soaps, alkylbenzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerin ether sulfonates, a-methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, alkyl ether sulfates, glycerin ether sulfates, fatty acid ether sulfate sulfates, fatty acid ether sulfate sulfates, fatty acid ether sulfate sulfates, fatty acid ether sulfate sulfates, fatty acid ether sulfate sulfates, fatty acid ether sulfate sulfates, fatty acid ether sulfate sulfates, fatty acid ether sulfate sulfates,
  • Acylamino acid salts such as, for example, acylglutamates, for example sodium acylglutamate, di-TEA palmitoyl aspartate and sodium caprylic / capric acid glutamate, acyl peptides, for example palmitoyl-hydrolysed milk protein, sodium cocoyl-hydrolyzed soy protein and sodium / hydrolysate collagen;
  • Alkyl ether sulfates such as, in particular, sodium, ammonium, magnesium, MI PA, TIPA laureth sulfate, sodium myreth sulfate and sodium C12-13 pareth sulfate;
  • Alkyl sulfates for example sodium, ammonium and TEA lauryl sulfate
  • Glyceride sulfates such as sodium coco-monoglyceride sulfate
  • Amide sulfates such as magnesium PEG-3 cocamide sulfate.
  • Alkylarylsulfonates in particular sodium C12-14 olefin sulfonate,
  • sulfosuccinates for example dioctyl sodium sulfosuccinate, disodium laureth sulfosuccinate, disodium lauryl sulfosuccinate and disodium undecyleneamido MEA sulfosuccinate;
  • sulfoacetates such as sodium lauryl sulfoacetate
  • sarcosinates for example myristoyl sarcosine, TEA lauroy isarcosinate, sodium lauroyl sarcosinate and sodium cocoylsarcosinate,
  • (I) isethionates, such as sodium / ammonium cocoyl isethionate,
  • taurates for example sodium lauroyl taurate and sodium methyl cocoyl taurate
  • Ether carboxylates such as sodium laureth-13 carboxylate and sodium PEG-6 cocamide carboxylate
  • phosphates such as cetyl phosphate (mono-, di-cetyl and their mixtures), potassium cetyl phosphate, (mono-, di-cetyl and their mixtures), DEA-cetyl phosphate (mono-, di-cetyl and their mixtures), DEA-oleth-10-phosphate and dilaureth-4-phosphate.
  • nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers or mixed formals, optionally partially oxidized alk (en) yl oligoglycidic acid derivatives or glucologlycoside derivatives or , Protein hydrolyzates (especially vegetable products based on wheat), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, these can have a conventional, but preferably a narrow, homolog distribution.
  • Cationic surfactants contain at least one N atom which is covalently bonded to 4 alkyl or aryl groups. This leads to a positive charge regardless of the pH. Alkylbe tain, alkylamidopropylbetaine and alkylamidopropylhydroxysultaine are advantageous.
  • the cationic surfactants used can furthermore preferably be selected from the group consisting of quaternary ammonium compounds, in particular benzyltrialkylammonium chlorides or bromides, such as, for example, benzyldimethylstearylammonium chloride, and alkyltrialkylammonium salts, for example cetyltrimethylammonium chloride or bromide, alkyldoniumchloride, alkyldimiumchloride or alkyldimiumchloride, or alkyldimiumchloride, kyldimethylammonium chlorides or bromides, alkylamidethyltrimethylammonium ether sulfates, alkylpyridinium salts, for example lauryl or cetylpyridinium chloride, imidazoline derivatives and compounds with a cationic character, such as amine oxides, for example alkyldimethylamine oxide or alkylaminoethyldimethylamine oxide.
  • amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • the surfactants mentioned are exclusively known compounds.
  • Typical examples of particularly suitable mild, ie particularly skin-compatible, surfactants are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and / or dialkyl kylsulfosuccinate, lutamate fatty acid taurides, Fett Textreg, a-olefinsulfonates, ether carboxylic acids, alkyl oligoglucosides, fatty acid glucamides, alkylamidobetaines, amphoacetals and / or protein fatty acid condensates, the latter preferably based on wheat proteins.
  • Guerbet alcohols based on fatty alcohols with 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C6-C22 fatty acids with linear or branched C6-C22 fatty alcohols or esters of branched C6-C13 carboxylic acids are, for example, Guerbet alcohols with linear or branched C6-C22 fatty alcohols, such as Myristyl myristate, myristyl palmitate ristylerucat, myristyl stearate, Myristylisostearat, myristyl, Myristylbehenat, mu-, cetyl myristate, cetyl palmitate, cetyl stearate, Cetylisostearat, cetyl oleate, cetyl behenate, Cetylerucat, Stearylmyristat, stearyl palmitate, stearyl stearate, Stearylisostearat, stearyl oleate,
  • esters of linear C6-C22 fatty acids with branched alcohols in particular 2-ethylhexanol
  • esters of Ci8-C38 alkylhydroxycarboxylic acids with linear or branched C6-C22 fatty alcohols in particular dioctyl malates
  • esters of linear or branched C6 -C13 carboxylic acids with linear or branched C6-C13 alcohols such as ethylhexyl isononanoate
  • triglycerides based on C 6 -Cio- Fatty acids liquid mono- / di- / triglyceride mixtures based on C o -Cis fatty acids
  • esters of C6-C22 fatty alcohols and / or Guerbet alcohols with
  • the amount used can be based on the final formulation between 5 and 80 wt .-%, preferably between 10 and 50 wt .-% and in particular between 20 and 40 wt .-%.
  • Suitable emulsifiers are, for example, nonionic surfactants from at least one of the following groups:
  • Partial esters of polyglycerol (average degree of self-condensation 2 to 8), polyethylene glycol (molecular weight 400 to 5000), trimethylolpropane, pentaerythritol, sugar alcohols (eg sorbitol), alkyl glucosides (eg methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucose (eg cellulose) saturated and / or unsaturated th, linear or branched fatty acids with 12 to 22 carbon atoms and / or hydroxycarboxylic acids with 3 to 18 carbon atoms and their adducts with 1 to 30 moles of ethylene oxide;
  • polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives • polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives; Block copolymers, for example polyethylene glycol 30 dipolyhydroxystearate;
  • polymer emulsifiers for example Pemulen types (TR-1, TR-2) from Lubrizol or Cosmedia ® SP from BASF;
  • Alkoxylates The adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols or with castor oil are known, commercially available products. These are homolog mixtures whose average degree of alkoxylation is the ratio of the amounts of ethylene oxide and / or propylene oxide and Substrate with which the addition reaction is carried out corresponds. C12 / 18 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known as refatting agents for cosmetic preparations.
  • Alkyl and / or alkenyl oligoglycoside Alkyl and / or alkenyl oligoglycosides, their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • the glycoside residue both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to preferably about 8 are suitable.
  • the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
  • Partial glycerides Typical examples of suitable partial glycerides are rinTalkremonoglycerid Hydroxystea-, hydroxystearic acid diglyceride, isostearic acid, Isostea- rinklarediglycerid, klarediglycerid oleic acid monoglyceride, oleic acid diglyceride, Ricinolklaremoglycerid, ricinoleic, Linolklaremonoglycerid, Linolklarediglycerid, Linolenklaremonoglycerid, Linolenklad, Erucaklaremonoglycerid, Erucaklarediglycerid, Weinklaremonogly- cerid, Weinklarediglycerid, Citronenklamonoglycerid, Citronendiglycerid, Citronendiglycerid, Malic acid monoglyceride, malic acid diglyceride and their technical mixtures, which may still contain minor amounts of t
  • Sorbitan esters As sorbitan esters sorbitan, sorbitan sesquiisostearat, sorbitan diisostearate, sorbitan triisostearate sesquioleate, sorbitan, sorbitan, sorbitan dioleate, trioleate, Sorbitanmonoerucat, Sorbitansesquierucat, Sorbitandierucat, Sorbitantrierucat, Sorbitanmonoricinoleat, Sorbitansesquiricinoleat, bitandiricinoleat sorting, Sorbitantriricinoleat, Sorbitanmonohydroxystearat, sorbitan sesquihydroxystearat , Sorbitan dihydroxystearate, sorbitan trihydroxystearate, sorbitan monotartrate, sorbitan sesquiartrate, sorbitan ditartrate, sorbitan tritartrate, sorbitan monocitrate, sor- bitansesquicit
  • Polyglycerol esters are polyglyceryl-2 dipolyhydroxystearate (Dehymuls® PGPH), polyglycerol-3-diisostearate (Lameform® TGI), polyglyceryl-4 isostearate (Isolan® Gl 34), polyglyceryl-3 oleate, diisostearoyl polyglyceryl- 3 diisostearates (Isolan® PDI), polyglyceryl-3 methylglucose distearate (Tego Care® 450), polyglyceryl-3 beeswax (Cera Bellina®), polyglyceryl-4 caprate (polyglycerol caprate T2010 / 90), polyglyceryl-3 cetyl ether (Chimexane® NL), Polyglyceryl-3 Distearate (Cremophor® GS 32) and Polyglyceryl Polyricinoleate (Admul® W
  • polystyrene resin examples include the mono-, di- and triesters of trimethylolpropane or pentaerythritol with lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like, optionally reacted with 1 to 30 mol of ethylene oxide.
  • Anionic emulsifiers are aliphatic fatty acids with 12 to 22 carbon atoms, such as, for example, palmitic acid, stearic acid or behenic acid, and dicarboxylic acids with 12 to 22 carbon atoms, such as, for example, azelaic acid or sebacic acid.
  • mono-, di- and trialkyl phosphates and mono-, di- and / or tri-PEG-alkyl phosphates and their salts such as potassium cetyl phosphate and the citra testers, especially glyceryl oleate citrate and glyceryl stearyl citrate.
  • zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the coconut acylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxylate -3-hydroxyethylimi- dazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium gly
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a Cs / is-alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO3H group in the molecule and are capable of forming internal salts.
  • suitable ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid.
  • ren N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-coconut alkylaminopropionate , the Kokosacylaminoethylaminopropionat and the Ci2 / i8-Acylsarcosin.
  • cationic surfactants are also suitable as emulsifiers, those of the esterquat type, preferably methylquaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • the amount of emulsifiers used is typically in the range from about 0.5 to about 10% by weight and preferably about 1 to about 5% by weight.
  • Typical examples of fats are glycerides, i.e. Solid or liquid vegetable or animal products, which essentially consist of mixed glycerol esters of higher fatty acids, come as waxes, among others. natural or synthetic waxes, e.g. Candelila wax, carnauba wax, Japanese wax, esparto grass wax, cork wax, guaruma wax, rice, germ oil wax, sugar cane wax, ouricury wax, montan wax, beeswax, shellac wax, walnut, lanolin (wool wax), pretzel fat, ceresin, ozokerite (earth wax), petrolatum, paraffin waxes chemically modified waxes (hard waxes), e.g.
  • natural or synthetic waxes e.g. Candelila wax, carnauba wax, Japanese wax, esparto grass wax, cork wax, guaruma wax, rice, germ oil wax, sugar cane wax, ouricury wax, montan wax, bee
  • Examples of natural lecithins are the cephalins, which are also referred to as phosphatidic acids and are derivatives of 1,2-diacyl-sn-glycerol-3-phosphoric acids.
  • phospholipids are usually understood to be mono- and preferably diesters of phosphoric acid with glycerol (glycerol phosphates), which are generally classed as fats.
  • glycerol phosphates glycerol phosphates
  • sphingosines or sphingolipids are also suitable.
  • Pearlescent waxes that can be used are, for example: alkylene glycol esters, especially ethylene glycol distearate; Fatty acid alkanolamides, especially coconut fatty acid diethanolamide; Partial glycerides, especially stearic acid monoglyceride; Esters of polyvalent, optionally hydroxy-substituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; Fatty substances, such as, for example, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which have a total of at least 24 carbon atoms, especially lauron and distearyl ether; Fatty acids such as stearic acid, hydroxystearin acid or behenic acid, ring opening products of olefin epoxides with 12 to 22 carbon atoms with fatty alcohols with 12 to 22 carbon atoms and / or polyols with 2 to 15
  • Coolants are compounds that create a feeling of cold on the skin.
  • these are menthol compounds which - in addition to the basic body menthol itself - are selected, for example, from the group formed by menthol methyl ether, menthone glyceryl acetal (FEMA GRAS 1 3807), menthone glyceryl ketal (FEMA GRAS 3808), menthyl lactate (FEMA GRAS 3748), menthol ethylene glycol carbonate (FEMA GRAS 3805), menthol propylene glycol carbonate (FEMA GRAS 3806), menthyl N-ethyloxamate, monomethyl succinate (FEMA GRAS 3810), monomenthyl glutamate (FEMA GRAS 4006), menthoxy-l, 2-propanediol (FEMA GRAS 3784), menthoxy-2-methyl-l, 2-propanediol (FEMA GRAS 3849) and the menthane carboxylic acid esters and amides WS
  • FEMA GRAS 3810 A first important representative of these substances is the monomenthyl succinate (FEMA GRAS 3810). Both the succinate and the analogous monomenthyl glutarate (FEMA GRAS 4006) are important representatives of monomenthyl esters based on di- and polycarboxylic acids:
  • FEMA stands for "Flavor and Extracts Manufacturers Association” and GRAS is defined as "Generally Regarded As Safe”.
  • a FEMA GRAS designation means that the substance labeled in this way is tested according to the standard method and is considered to be toxicologically safe. corresponding sugar derivatives.
  • FEMA GRAS 3807 menthone glyceryl acetal
  • FEMA GRAS 3808 menthone glyceryl ketal
  • menthone glyceryl acetal / ketal and menthyl lactate as well as menole ethylene glycol carbonate and menthol propylene glycol carbonatew have proven to be particularly advantageous, which the applicant under the names Frescolat ® MGA, Frescolat ® ML, Frecolat ® MGC and Frescolat ® MPC sells.
  • menthol compounds were first developed which have a C-C bond in the 3-position and of which a number of representatives can also be used. These substances are generally referred to as WS types.
  • the basic body is a menthol derivative in which the hydroxyl group is replaced by a carboxyl group (WS-1). All other WS types are derived from this structure, such as, for example, the preferred species WS-3, WS-4, WS-5, WS-12, WS-14 and WS-30.
  • consistency agents are primarily fatty alcohols or hydroxy fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and also partial glycerides, fatty acids or hydroxy fatty acids.
  • a combination of these substances with alkyl oligoglucosides and / or fatty acid N-methylglucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred.
  • Suitable thickeners are, for example, Aerosil types (hydrophilic silicas), polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl and hydroxypropyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates , (e.g. Carbopole® and Pemulen types from Lubrizol; Synthalene® from Sigma; Keltrol types from Kelco; Sepigel types from Seppic; Salcare types from BASF), polyacrylamides, polymers, polyvinyl alcohol and polyvinyl pyrrolidone.
  • Aerosil types hydrophilic silicas
  • polysaccharides in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl and hydroxypropyl
  • Bentonites such as Bentone ® Gel VS-5PC (Elementis), which is a mixture of cyclopentasiloxane, disteardimonium hectorite and propylene carbonate, have also proven to be particularly effective.
  • Surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides as well as electrolytes such as sodium chloride and ammonium chloride are also suitable.
  • LUBRICANTS AND STABILIZERS are also suitable.
  • Substances such as lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Metal salts of fatty acids such as e.g. Magnesium, aluminum um and / or zinc stearate or ricinoleate are used.
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, such as e.g. a quaternized hydroxyethyl cellulose available under the name Polymer JR 400® from Dow, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers such as e.g.
  • Luviquat® condensation products of polyglycols and amines, quaternized collagen polypeptides, such as, for example, lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / BASF), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, such as e.g.
  • Amodimethicones, copolymers of adipic acid and dimethylaaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Lubrizol), polyaminopolyamides and their crosslinked water-soluble polymers, if appropriate, cationic chitinated products, such as quinine derivatives, quaternized derivatives such as quanine derivatives, from dihaloalkylene, such as Dibromobutane with bisdialkylamines, e.g. Bis-dimethylamino-1,3-propane, cationic guar gum, e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 (Sol vay), quaternized ammonium salt polymers, e.g. Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 (Solvay).
  • Anionic, zwitterionic, amphoteric and nonionic polymers include, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic acid anhydride copolymers and their copolymers and polyols crosslinked with polyols, acrylamidopropyltrimethylammonium chloride / acrylate copolymers, octylacrylamide / methyl methacrylate / tert.butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers / vinylpyramolidone methacrylate and vinylpyramolamino-vinylamides, and dated cellulose
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds which are both liquid and resinous at room temperature can.
  • Simethicones which are mixtures of dimethicones with an average chain length of 200 to 300 dimethylsiloxane units and hydrogenated silicates, are also suitable.
  • the diesters according to the invention are in particular able to overcome the stickiness that is typical of many UV filters.
  • Another object of the present invention therefore relates to preparations which further contain at least one UV filter in addition to the diesters. In particular, such preparations are preferred which
  • UV light protection filter (synonymous often referred to as light protection factors) are to be understood, for example, at room temperature liquid or crystalline organic substances which are able to absorb ultraviolet rays and which absorb energy in the form of long-wave radiation, e.g. To give off heat again.
  • the UV light protection filter is usually present in amounts of 0.1 to 50 and preferably 1 to 45% by weight.
  • Typical UV-A filters include, in particular, derivatives of benzoylmethane, such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-l, 3-dione, 4- tert.-Butyl-4'-methoxydibenzoylmethane (Neo Heliopan ® 357), 2- (4-diethylamino-2-hydroxy-benzoyl) -benzoic acid hexyl ester (Uvinul® A Plus), l-phenyl-3- (4'- isopropylphenyl) propane-1,3-dione and enamine compounds.
  • benzoylmethane such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-l, 3-dione, 4- tert.-Butyl-4'-methoxydibenzoylmethane (Neo Heliopan ® 357), 2- (4
  • menthyl anthranilate (Neo Heliopan ® MA);
  • UVB filters can be oil-soluble or water-soluble.
  • oil-soluble substances e.g. to call:
  • menthyl anthranilate (Neo Heliopan ® MA);
  • Tris (2-ethylhexyl) 4,4 ', 4 "- (l, 3,5-triazine-2,4,6-triyltriimino) tribenzoate (Uvinul ® T150);
  • Suitable broadband filters include, for example:
  • Tris-Biphenyl Triazine (Tinosorb ® A2B);
  • UV-A and UV-B filters can of course also be used in mixtures.
  • Particularly favorable combinations consist of the derivatives of benzoylmethane, e.g. 4-tert-butyl-4'-methoxydibenzoylmethane (Neo Heliopan ® 357) and 2-cyano-3,3-phenylcinnamic acid 2-ethyl-hexyl ester (octocrylene) in combination with esters of cinnamic acid, preferably 2-ethylhexyl 4-methoxycinnamate and / or propyl 4-methoxycinnamate and / or isoamyl 4-methoxycinnamate.
  • benzoylmethane e.g. 4-tert-butyl-4'-methoxydibenzoylmethane (Neo Heliopan ® 357)
  • Such combinations are advantageous ions combined with water-soluble filters such as 2-phenylbenzimidazole-5-sulfonic acid and their alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium and glucammonium salts.
  • water-soluble filters such as 2-phenylbenzimidazole-5-sulfonic acid and their alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium and glucammonium salts.
  • insoluble light-protection pigments namely finely dispersed metal oxides or salts
  • suitable metal oxides are, in particular, zinc oxide and titanium dioxide and, in addition, oxides of iron, zirconium, silicon, manganese, aluminum and cerium and mixtures thereof.
  • Silicates (talc), barium sulfate or zinc stearate can be used as salts.
  • the oxides and salts are used in the form of the pigments for skin-care and skin-protecting emulsions and decorative cosmetics.
  • the particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm.
  • the pigments can also be surface-treated, ie hydrophilized or hydrophobized.
  • Typical examples are coated titanium dioxides such as titanium dioxide T 805 (Degussa) or Eusolex ® T2000, Eusolex ® T, Eusolex ® T-ECO, Eusolex ® TS, Eusolex ® T-Aqua, Eusolex ® T-45D (all Merck), Uvinul T1O2 (BASF).
  • Silicones and in particular trialkoxyoctylsilanes or simethicones, are particularly suitable as hydrophobic coating agents. So-called micro- or nanopigments are preferably used in sunscreens. Micronized zinc oxide such as Z-COTE ® or Z-COTE HP1 ® is preferably used.
  • Humectants serve to further optimize the sensory properties of the composition and to regulate the moisture of the skin. At the same time, the low-temperature stability of the preparations according to the invention, in particular in the case of emulsions, is increased.
  • the humectants are usually present in an amount of 0.1 to 15% by weight, preferably 1 to 10% by weight, and in particular 5 to 10% by weight.
  • Suitable according to the invention include amino acids, pyrrolidone carboxylic acid, lactic acid and their salts, lactitol, urea and urea derivatives, uric acid, glucosamine, crea tinin, cleavage products of collagen, chitosan or chitosan salts / derivatives, and in particular polyols and polyol derivatives (e.g.
  • Glycerin diglycerin, triglycerin, ethylene glycol, propylene glycol, butylene glycol, erythritol, 1,2,6-hexanetriol, polyethylene glycols such as PEG-4, PEG-6, PEG-7, PEG-8, PEG-9, PEG-10 , PEG-12, PEG-14, PEG-16, PEG-18, PEG-20), sugar and sugar derivatives (including fructose, glucose, maltose, maltitol, mannitol, inositol, sorbitol, sorbitylsilanediol, sucrose, trehalose, xylose, xylitol , Glucuronic acid and its salts), ethoxylated sorbitol (Sorbeth-6, Sorbeth-20, Sorbeth-30, Sorbeth-40), honey and hardened honey, hardened starch hydrolysates and mixtures of hardened wheat protein and PEG-20 a
  • Biogenic active ingredients include, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, (deoxy) ribonucleic acid and its fragmentation products, ⁇ -glucans, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino pseudo acids, ceramides, ceramides, ceramides, ceramides essential oils, plant extracts, such as Prunus extract, Bambaranus extract and vitamin complexes to understand.
  • Antioxidants interrupt the photochemical reaction chain which is triggered when UV radiation penetrates the skin.
  • Typical examples are amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g. Anserine), carotenoids, carotenes (e.g. a-carotene, ß-carotene, lycopene) and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (e.g.
  • thiols e.g. thioredoxin, glutathione, Cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, g-linoleyl, cholesteryl and glyceryl esters
  • salts dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (eg buthioninsulfoximines, homocysteine sulfoximine, butioninsulfones, penta- in
  • Cosmetic deodorants counteract, mask or eliminate body odors.
  • Body odors arise from the action of skin bacteria on apocrine sweat, whereby unpleasant smelling breakdown products are formed. Accordingly, deodorants contain active ingredients that act as germ-inhibiting agents, enzyme inhibitors, odor absorbers or odor maskers.
  • Germ inhibitors In principle, all substances effective against gram-positive bacteria are suitable as antimicrobial agents, such as. B. 2-methyl-5-cyclohexylpentanol, 1,2-decylene glycol, 4-hydroxybenzoic acid and its salts and esters, N- (4-chlorophenyl) -N'- (3,4-dichlorophenyl) urea, 2,4,4 '-Trichlor-2'-hydroxy-diphenyl ether (triclosan), 4-chloro-3,5-dimethyl-phenol, 2,2'-methylene-bis (6-bromo-4-chlorophenol), 3-methyl-4- (l-methylethyl) phenol, 2-benzyl-4-chlorophenol, 3- (4-chlorophenoxy) -l, 2-propanediol, 3-iodo-2-propynyl butyl carbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC ),
  • Enzyme inhibitors are suitable as enzyme inhibitors. These are preferably trialkyl citrates such as trimethyl citrate, tripropy citrate, triisopropyl citrate, tributyl citrate and in particular triethyl citrate (Hydagen® CAT). The substances inhibit enzyme activity and thereby reduce odor.
  • trialkyl citrates such as trimethyl citrate, tripropy citrate, triisopropyl citrate, tributyl citrate and in particular triethyl citrate (Hydagen® CAT).
  • esterase inhibitors include sterolsulfates or phosphates, such as, for example, lanosterol, cholesterol, campesterin, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and their esters, such as, for example, glutaric acid, glutaric acid monoethyl ester, Glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic acid diethyl ester, hydroxycarboxylic acids and their esters such as citric acid, malic acid, tartaric acid or tartaric acid diethyl ester, and zinc glycinate.
  • sterolsulfates or phosphates such as, for example, lanosterol, cholesterol, campesterin, stigmasterol and sitosterol sulfate or phosphate
  • dicarboxylic acids and their esters such as, for
  • Odor absorber Suitable as odor absorbers are substances that absorb odor-forming compounds and can largely retain them. They lower the partial pressure of the individual components and thus also reduce their speed of propagation. It is important that perfumes have to remain unaffected. Odor absorbers are not effective against bacteria. They contain, for example, the main constituent of a complex zinc salt of ricinoleic acid or special, largely odorless fragrances that are known to the person skilled in the art as "fixators", such as. B. extracts of Labdanum or Styrax or certain abietic acid derivatives. Fragrances or perfume oils act as odor maskers, which, in addition to their function as odor maskers, give the deodorants their respective fragrance.
  • Perfume oils include, for example, mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers, stems and leaves, fruits, fruit peels, roots, woods, herbs and grasses, needles and branches, as well as resins and balms. Animal raw materials, such as civet and castoreum, are also suitable. Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type.
  • Fragrance compounds of the ester type are, for example, benzyl acetate, p-tert-butylcyclohexyl acetate, linalyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, allyl cyclohexyl propionate, styrallyl propionate and benzylsa licylate.
  • the ethers include, for example, benzyl ethyl ether
  • the aldehydes include, for example, the linear alkanes with 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal
  • the ketones for example, the jonones and methylcedryl ketone
  • the alcohols bring anethole
  • Citronellol Citronellol
  • eugenol isoeugenol
  • geraniol linalool
  • the hydrocarbons mainly include the terpenes and balsams.
  • fragrance oils are also suitable as perfume oils, e.g. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, lavender oil and lavender oil.
  • Antiperspirants reduce sweat formation by influencing the activity of the eccrine sweat glands and thus counteract armpit wetness and body odor.
  • Aqueous or anhydrous formulations of antiperspirants typically contain the following ingredients:
  • Excipients such as B. thickeners or complexing agents and / or
  • non-aqueous solvents such as As ethanol, propylene glycol and / or glycerin.
  • Salts of aluminum, zirconium or zinc are particularly suitable as astringent antiperspirant active ingredients.
  • suitable antiperspirant active ingredients are, for example, aluminum chloride, aluminum chlorohydrate, aluminum dichlorohydrate, aluminum sesquichlorohydrate and their complex compounds, for. B. with propylene glycol-1,2.
  • customary oil-soluble and water-soluble auxiliaries can be contained in small amounts in antiperspirants. Examples of such oil-soluble auxiliaries are:
  • water-soluble additives are e.g. Preservatives, water-soluble fragrances, pH adjusting agents, e.g. Buffer mixtures, water soluble thickeners, e.g. what is soluble in natural or synthetic polymers such as Xanthan gum, hydroxyethyl cellulose, polyvinyl pyrrolidone or high molecular weight polyethylene oxides.
  • Customary film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, hydrolyzed jojobester, col or compounds thereof, hyaluronic acid.
  • Suitable antidandruff active ingredients are piroctone olamine (l-hydroxy-4-methyl-6- (2,4,4-trimythylpentyl) -2- (lH) -pyridinonmonoethanolaminsalz) toconazol®, Crinipan ® AD (Climbazole), Ke, (4-Acetyl-l - ⁇ - 4- [2- (2.4-dichlorophenyl) r-2- (1H-imidazol-l-ylmethyl) -l, 3-dioxylan-c-4-ylmethoxyphenyl ⁇ piperazine, ketoconazole, elubiol , Selenium disulfide, sulfur colloidal, sulfur polyethylene glycol sorbitan monooleate, sulfur ricinole polyhexylate, sulfur tar distillates, salicylic acid (or in combination with hexachlorophene), undexylenic acid monoethanolamide sulfosuccinate sodium salt, la
  • Montmorillonites, clay minerals, pemules and alkyl-modified carbopol types (lubrizole) can serve as swelling agents for aqueous phases. Further suitable polymers or swelling agents can be found in the overview by R. Lochhead in Cosm.Toil. 108, 95 (1993).
  • Suitable insect repellents are N, N-diethyl-m-toluamide, 1,2-pentanediol or ethyl butylacetylaminopropionate. Dihydroxyacetone is suitable as a self-tanner.
  • Examples of possible tyrosine inhibitors which prevent the formation of melanin and are used in depigmentants are arbutin, ferulic acid, kojic acid, coumaric acid and ascorbic acid (vitamin C).
  • Toothpastes or toothpastes are generally understood to mean gel-like or pasty preparations made from water, thickeners, humectants, abrasive or cleaning bodies, surfactants, sweeteners, flavorings, deodorising active substances and active substances against mouth and tooth diseases.
  • all usual cleaning bodies such as. B. chalk, dicalcium phosphate, insoluble sodium metaphosphate, aluminum silicates, calcium pyrophosphate, finely divided synthetic resins, silica, aluminum oxide and aluminum oxide trihydrate can be used.
  • Particularly suitable cleaning materials for the toothpastes according to the invention are, in particular, finely divided xerogel silicas, hydrogel silicas, precipitated silicas, aluminum oxide trihydrate and finely divided alpha-aluminum oxide or mixtures of these cleaning substances in amounts of 15 to 40% by weight of the toothpaste.
  • Mainly low molecular weight polyethylene glycols, glycerol, sorbitol or mixtures of these products in amounts of up to 50% by weight are suitable as humectants.
  • the known thickeners are the thickening, finely divided gel silicas and hydrocolloids, such as. B.
  • carboxymethyl cellulose hydroxyethyl cellulose, hydroxypropyl guar, hydroxyethyl starch, polyvinyl pyrrolidone, high molecular weight polyethylene glycol, plant gums such as tragacanth, agar, carrageenan moss, gum arabic, xantham gum and carboxy vinyl polymers (e.g. Carbopol ® types) are suitable.
  • the oral and dental care products can contain, in particular, surface-active substances, preferably anionic and nonionic high-foaming surfactants, such as the substances already mentioned above, but in particular alkyl ether sulfate salts, alkyl polyglucosides and mixtures thereof.
  • surface-active substances preferably anionic and nonionic high-foaming surfactants, such as the substances already mentioned above, but in particular alkyl ether sulfate salts, alkyl polyglucosides and mixtures thereof.
  • anti-calculus agents e.g. B. organophosphates such as 1-hydroxyethane-1,1-diphosphonic acid, l-phosphonopropane-l, 2,3-tricarboxylic acid and others which, for. B. from US 3,488,419, DE 2224430 Al and DE 2343196 Al are known;
  • sweeteners such as B. saccharin sodium, sodium cyclamate, sucrose, lactose, mal tose, fructose or Apartam ® , (L-aspartyl-L-phenylalanine methyl ester), Stivia extracts or their sweetening components, in particular ribeaudiosides;
  • buffer substances such as B. primary, secondary or tertiary alkali phosphates or citric acid / sodium citrate;
  • wound healing and anti-inflammatory substances such as B. allantoin, urea, azulene, chamomile active ingredients and acetylsalicylic acid derivatives.
  • a preferred embodiment of the cosmetic preparations are toothpastes in the form of an aqueous, pasty dispersion containing polishing agents, humectants, viscosity regulators and, if appropriate, other customary components, and the mixture of menthofuran and menthol compounds in amounts of 0.5 to 2% by weight. % contain.
  • a combination with aqueous-alcoholic solutions of various degrees of roughness of essential oils, emulsifiers, astringent and toning drug extracts, tartar-inhibiting, antibacterial additives and taste corrections is readily possible.
  • Another preferred embodiment of the invention is a mouthwash in the form of an aqueous or aqueous-alcoholic solution containing the mixture of menthofuran and menthol compounds in amounts of 0.5 to 2% by weight.
  • hydrotropes such as ethanol, isopropyl alcohol or polyols can also be used; these substances largely correspond to the carriers described above.
  • Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups.
  • the polyols can also contain further functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are
  • Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, pentylene glycol, caprylyl glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;
  • Methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Lower alkyl glucosides in particular those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;
  • Sugar alcohols with 5 to 12 carbon atoms such as sorbitol or mannitol,
  • Aminosugars such as glucamine
  • dialcohol amines such as diethanolamine or 2-amino-1,3-propanediol.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, o-cymen-5-ol, tropolone or sorbic acid and the silver complexes known under the name Surfacine ® and those listed in Appendix 6, Parts A and B of the Cosmetics Regulation other substance classes.
  • Natural fragrances are extracts of flowers (lily, lavender, rose, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon , Oranges), roots (mace, angelica, celery, cardamom, costus, iris, calmus), wood (pine, sand egg, guaiac, ze- Thorn, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), needles and twigs (spruce, fir, pine, mountain pine), resins and balsams (galbanum, elemi, ben zoe, myrrh, olibanum, opoponax).
  • Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethyl methylphenylglycinate, allylcyclohexylpropylate propylate, styl pentylate.
  • the ethers include, for example, benzylethyl ether
  • the aldehydes include, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal
  • the ketones include, for example, the jonones, a-isomethylionone and methylcedrenyl ketone Anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpinol
  • the hydrocarbons mainly include terpenes and balms.
  • fragrance oils which are mostly used as aroma components, are also suitable as perfume oils, e.g. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil.
  • flavors are peppermint oil, spearmint oil, anise oil, star anise oil, caraway oil, eucalyptus oil, fennel oil, lemon oil, wintergreen oil, clove oil, menthol and the like.
  • dyes suitable for cosmetic purposes and approved substances can be used, as compiled, for example, in the publication "Cosmetic Colorants” of the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. Examples are culinary red A (Cl 16255), patent blue V (C.1.42051), indigotine (C.1.73015), chlorophyllin (C.1.75810), quinoline yellow (Cl47005), titanium dioxide (Cl77891), indanthrene blue RS (Cl 69800) and madder varnish (Cl58000). Luminol can also be present as the luminescent dye. These dyes are usually used in concentrations of 0.001 to 0.1 wt .-%, based on the entire mixture.
  • compositions according to the invention are selected from the group of products for the treatment, protection, care and cleaning of the skin and / or the hair or as a make-up product, either as leave-on or rinse-off products.
  • the formulations comprise, for example, dispersions, suspensions, creams, lotions or milk, depending on the production method and ingredients, gels (including hydrogels, for example hydrodispersion gels, oleogels), sprays (for example pump sprays or sprays with propellant), foams or impregnating solutions for cosmetic wipes, soaps, washing liquids, shower and bath preparations, bath products (capsules, oil, tablets, salts, bath salts, soaps, etc.), effervescent preparations, skin care products, such as, for example Emulsions, ointments, pastes, gels (as described above), oils, balms, serums, powders (e.g.
  • Styling aids e.g. gel or wax
  • hair straightening agents detangling agents, relaxation agents
  • hair coloring agents such as Temporary hair dye, semi-permanent hair dye, permanent hair dye, hair conditioner, hair foam, eye care products, make-ups, make-up remover or baby products.
  • the formulations according to the invention are particularly preferably in the form of an emulsion, in particular in the form of a W / O, O / W, W / O / W, O / W / O emulsion, PIT emulsion, B. a Pickering emulsion, a low oil emulsion, a micro or nano emulsion, a gel (including hydrogel, hydrodispersion gel, oleogel) or a solution.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40% by weight, based on the composition.
  • the agents can be produced by customary cold or hot processes; or also according to the phase inversion temperature method. INDUSTRIAL APPLICABILITY
  • Another object of the invention relates to the use of the diesters according to the invention as oil components and in particular as a replacement for silicone compounds in cosmetic preparations.
  • Also claimed is a method for improving the sensory properties of a cosmetic preparation comprising or consisting of the following steps:
  • the cosmetic preparations are preferably sunscreens which contain at least one UV filter.
  • Carbopol 980 Carbomer 0.3 0.3 0.3 0.3 0.3 0.3
  • Tackiness 3.0 2.5 1.5 1.0
  • the cream according to the invention is distinguished from all comparative products by a higher spreading capacity and a significantly lower stickiness.

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Abstract

L'invention concerne des diesters de 1,3-propanediol comprenant des acides gras linéaires comportant 6 à 22 atomes de carbone et 0 ou 1 à 3 doubles liaisons, sous réserve que le 1,3-propanediol de même que les acides gras soient exclusivement d'origine végétale.
EP19701066.3A 2019-01-15 2019-01-15 Diesters de 1,3-propanediol végétal Withdrawn EP3911296A1 (fr)

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Publication number Priority date Publication date Assignee Title
NL149701C (nl) 1965-12-08 1981-05-15 Procter & Gamble Werkwijze voor het bereiden van een tegen tandsteen werkzaam tandverzorgingsmiddel, dat als werkzaam bestanddeel een fosfonzuurderivaat bevat, alsmede gevormd tandverzorgingsmiddel.
DE2224430C3 (de) 1972-05-19 1980-10-09 Henkel Kgaa, 4000 Duesseldorf Zahnsteinbildung verhindernde Mund- und Zahnpflegemittel
DE2343196C3 (de) 1973-08-27 1980-01-10 Henkel Kgaa, 4000 Duesseldorf Aiacycloalkan-2^-diphosphonsäuren oder deren wasserlösliche Salze
US4959586A (en) * 1988-05-24 1990-09-25 U.S. Philips Corporation Electric incandescent lamp
DE19623383C2 (de) 1996-06-12 1999-07-01 Henkel Kgaa Verwendung von Fettstoffen als Siliconersatz zur Herstellung von kosmetischen und/oder pharmazeutischen Zubereitungen
RU2303362C2 (ru) 2001-11-23 2007-07-27 Юнилевер Н.В. Пищевой продукт с холодящим действием и способ его получения
US20030161802A1 (en) 2002-02-05 2003-08-28 Flammer Linda J. Anti-dandruff and anti-itch compositions containing sensate and sensate enhancer-containing compounds
KR20130027058A (ko) 2005-03-04 2013-03-14 코그니스 아이피 매니지먼트 게엠베하 특이적 분지형 탄화수소 기재의 연화제 및 미용 조성물
JP2011503192A (ja) 2007-11-13 2011-01-27 プレスパース、エルエルシー 風合いおよび揮発性を付与するシリコンフリーな炭化水素類
JP5861241B2 (ja) * 2010-03-12 2016-02-16 日清オイリオグループ株式会社 皮膚外用組成物、化粧料、及び洗浄剤
FR2968546B1 (fr) * 2010-12-14 2013-02-01 Oreal Procede de deformation permanente et notamment de lissage comprenant une etape de lissage des fibres keratiniques mettant en oeuvre une composition comprenant au moins 40% en poids de corps gras non silicones
EP3360600B1 (fr) 2011-11-14 2021-08-11 Inolex Investment Corporation Substituts de silicone naturel pour des fluides de silicone dans des formulations de soins personnels
WO2016040956A1 (fr) * 2014-09-12 2016-03-17 Vantage Specialty Chemicals, Inc. Dérivés de 1,3-propanediol

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US20220211598A1 (en) 2022-07-07

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