WO2002032380A2 - Emulsions cosmetiques - Google Patents
Emulsions cosmetiques Download PDFInfo
- Publication number
- WO2002032380A2 WO2002032380A2 PCT/EP2001/011547 EP0111547W WO0232380A2 WO 2002032380 A2 WO2002032380 A2 WO 2002032380A2 EP 0111547 W EP0111547 W EP 0111547W WO 0232380 A2 WO0232380 A2 WO 0232380A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- esters
- alcohols
- fatty
- branched
- Prior art date
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- 239000008271 cosmetic emulsion Substances 0.000 title claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 44
- 239000000178 monomer Substances 0.000 claims abstract description 29
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 26
- 229920000126 latex Polymers 0.000 claims abstract description 18
- 229920000642 polymer Polymers 0.000 claims abstract description 18
- 239000004816 latex Substances 0.000 claims abstract description 6
- -1 alkyl hydroxycarboxylic acids Chemical class 0.000 claims description 73
- 239000000194 fatty acid Substances 0.000 claims description 57
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 56
- 229930195729 fatty acid Natural products 0.000 claims description 56
- 150000002148 esters Chemical class 0.000 claims description 47
- 239000003921 oil Substances 0.000 claims description 44
- 150000004665 fatty acids Chemical class 0.000 claims description 43
- 235000019198 oils Nutrition 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 29
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- 150000002191 fatty alcohols Chemical class 0.000 claims description 23
- 150000001298 alcohols Chemical class 0.000 claims description 18
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- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 229920005862 polyol Polymers 0.000 claims description 13
- 230000036961 partial effect Effects 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 7
- 239000012074 organic phase Substances 0.000 claims description 7
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- 150000003626 triacylglycerols Chemical class 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
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- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 8
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
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- 239000004094 surface-active agent Substances 0.000 description 7
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- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 6
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
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- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 1
- ARCJQKUWGAZPFX-UHFFFAOYSA-N stilbene oxide Chemical compound O1C(C=2C=CC=CC=2)C1C1=CC=CC=C1 ARCJQKUWGAZPFX-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000005555 sulfoximide group Chemical group 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 210000000106 sweat gland Anatomy 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- HBPNTDBLHQHPLH-UHFFFAOYSA-N tetradecyl 16-methylheptadecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C HBPNTDBLHQHPLH-UHFFFAOYSA-N 0.000 description 1
- AVKVDDQTHIQFSC-UHFFFAOYSA-N tetradecyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC AVKVDDQTHIQFSC-UHFFFAOYSA-N 0.000 description 1
- DHZWALZKPWZSMA-UHFFFAOYSA-N tetradecyl oleate Natural products CCCCCCCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC DHZWALZKPWZSMA-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- FQAZRHVERGEKOS-UHFFFAOYSA-N tripropan-2-yl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC(C)OC(=O)CC(O)(C(=O)OC(C)C)CC(=O)OC(C)C FQAZRHVERGEKOS-UHFFFAOYSA-N 0.000 description 1
- ODHUFJLMXDXVRC-UHFFFAOYSA-N tripropyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCOC(=O)CC(O)(C(=O)OCCC)CC(=O)OCCC ODHUFJLMXDXVRC-UHFFFAOYSA-N 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229940071566 zinc glycinate Drugs 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
- UOXSXMSTSYWNMH-UHFFFAOYSA-L zinc;2-aminoacetate Chemical compound [Zn+2].NCC([O-])=O.NCC([O-])=O UOXSXMSTSYWNMH-UHFFFAOYSA-L 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/34—Higher-molecular-weight carboxylic acid esters
-
- 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
-
- 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
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
-
- 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
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
-
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
- C09K23/018—Mixtures of two or more different organic oxygen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
Definitions
- the invention is in the field of cosmetic emulsions and relates to special emulsions containing novel latices and a process for their preparation.
- latex means that the cosmetic chemist understands colloidal dispersions of polymers in aqueous media. Such dispersions are generally milky-white liquids which are low-viscosity even at relatively high polymer contents, but which crosslink as a function of the pH and can build up very high viscosities even when diluted strongly. For this reason, latices, especially those based on polyacrylates, are used as thickeners for cosmetic preparations.
- the object of the invention was to produce cosmetic O / W emulsions containing latices which, compared to the prior art, have improved tactile properties and a faster absorption capacity and at the same time have pH values in the range of 3 let set to 5 without causing a collapse in concentration.
- the preparations should contain 3% by weight aqueous dilution even at a pH of 3 still have a Brookfield viscosity (25 ° C, 2 rpm) of at least 80,000 mPas.
- Another object has been to provide a process for the preparation of the emulsions, which should be distinguished above all by the fact that it allows preparations with a solids content in the range from 30 to 50% by weight to be produced without this being distilled or another concentration step is required.
- the invention relates to cosmetic emulsions containing oil bodies, emulsifiers and polymers of the latex type, which are distinguished in that the latices are obtained exclusively by condensation of monomers with strong acid functions and co-monomers which either have a weak acid function or react neutrally ,
- emulsions containing the latices according to the invention are distinguished by much better tactile properties compared to commercial products and are absorbed into the skin much more quickly.
- the preparations can contain the latices in amounts of 15 to 65 and preferably 30 to 50% by weight, based on the emulsions, and in turn serve as a consistency agent for the production of cosmetic end products, in which they are present in amounts of 1 to 10, preferably 2 up to 5 wt .-% can be included.
- the invention further relates to a process for the preparation of cosmetic O / W emulsions containing latex-type polymers, in which
- phase (A) firstly an aqueous phase (A) containing monomers capable of polymerization with a strong acid function (Ml) and also co-monomers (M2) which are also capable of polymerization and which are distinguished by a weak acid function, and an organic phase (B) containing Oil body and W / O emulsifiers, (b) the phases (A) and (B) intimately mixed, and
- A aqueous phase
- Ml strong acid function
- M2 co-monomers
- the monomers contained in the W / O emulsion thus obtained are polymerized in a manner known per se with phase inversion.
- the advantage of this process is that O / W emulsions with solids contents in the desired range of 30 to 50% by weight are obtained in one step without the need for a distillation or concentration step.
- Another advantage is that the emulsions can also be adjusted to acidic pH values without the viscosity collapsing.
- Suitable monomers and co-monomers are distinguished by the fact that they have structural features which enable them to polymerize; these are preferably double bonds.
- Appropriate unsaturated carboxylic acids preferably acrylic acid, methacrylic acid and mixtures thereof are suitable as monomers (MI) which are additionally distinguished by a strong acid function;
- unsaturated dicarboxylic acids such as malonic or fumaric acid can also be used.
- esters or amides of these carboxylic acids are esters or amides of these carboxylic acids.
- Typical examples are the esters of acrylic acid and / or methacrylic acid with C 1 -C 22 alcohols such as methanol, ethanol, allyl alcohol, the isomeric propanols, butanols and pentanols and fatty alcohols, as are caprone alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecy - Alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, elausestearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol and brassidyl alcohol, and erucy
- the esters are preferably derived from unsaturated alcohols, so that double bonds are available for the polymerization both in the acid component and in the alcohol component. Accordingly, esters based on allyl alcohol are particularly preferred.
- the amides can be derived accordingly from primary or secondary C 4 C 4 amines, such as methylamine, dimethylamine, ethylamine, diethylamine, propylamine, dipropylamine and the various butylamines and di-butylamines. Also possible are oligoamines, such as, for example, diethylene triamine, tripropylenetetramine or alkanolamines, such as, for example, ethanolamine, propanolamine and the like.
- bridged amides can also result, which are also suitable for the polymerization.
- a typical example of this is bisacrylamide.
- the co-monomers are usually used in amounts of 5 to 100 preferably 10 to 50 and in particular 15 to 25 mol%, based on the monomers.
- esters of linear C 6 -C 22 fatty acids with linear or branched C 6 -C 22 fatty alcohols or esters of branched C 6 -C ⁇ come as oil bodies, for example 3 - carboxylic acids with linear or branched C 6 -C 22 fatty alcohols, such as myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl rucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl stearate, cetyl stearate, cetyl stearate, cetyl stearate, cetyl stearate, cetyl stearate, cetyl stearate, cetyl stearate, cetyl stearate, cetyl stearate, cetyl stearate, cetyl
- esters of linear C 6 -C 22 fatty acids with branched alcohols in particular 2-ethylhexanol
- esters of C 8 -C 38 alkylhydroxycarboxylic acids with linear or branched C 6 -C 22 fatty alcohols cf.
- dioctyl malates especially dioctyl malates, esters of linear and / or branched fatty acids with polyhydric alcohols (such as propylene glycol, dimer diol or trimer triol) and / or Guerbet alcohols, triglycerides based on C 6 -C 0 fatty acids, liquid mono- / di- / triglyceride mixtures based of C 6 -C 8 fatty acids, esters of C 6 -C 22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, especially benzoic acid, esters of C 2 -C 2 dicarboxylic acids with linear or branched alcohols with 1 to 22 carbon atoms or polyols with 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C 6 -C 22 fatty alcohol carbonates, such as dicaprylyl carbonates
- TN linear or branched, symmetrical or asymmetrical dialkyl ethers with 6 to 22 carbon atoms per alkyl group, such as dicaprylyl ether (Cetiol® OE), ring opening products of epoxidized fatty acid esters with polyols, silicone oils (cyclomethicones, silicon methicone types, etc.) and / or aliphatic or naphthenic hydrocarbons, such as squalane, squalene or dialkylcyclohexanes.
- W / O emulsifiers such as squalane, squalene or dialkylcyclohexanes.
- W / O emulsifiers which are used in the first step of the process is in itself not very critical. Typical examples are adducts of 1 to 20 moles of ethylene oxide with hydroxy-functionalized triglycerides, which are commercially available, for example, under the name PEG Hydrogenated Castor Oil (Dehymuls® HRE 7). Polyglycerol esters, such as e.g. Polyglyceryl-2 dipolyhydroxystearate (Dehymuls® PGPH) or Polyglyceryl-3 diisostearate (Lameform® TGI) as well as certain partial glycerides, e.g. Glyceryl Oleate (Monomuls® 90-O 18).
- Polyglycerol esters such as e.g. Polyglyceryl-2 dipolyhydroxystearate (Dehymuls® PGPH) or Polyglyceryl-3 diisostearate (Lameform® TGI) as well as certain partial glycerides,
- W / O emulsifier mixtures are also commercially available, e.g. Dicocoyl Pentaerythryl Distearyl Citrate (and) Sorbitan Sesquioleate (and) Cera Alba (and) Aluminum Stearate (Dehymuls® E) or Dicocoyl Pentaerythryl Distearyl Citrate (and) Cera Microcrystallina (and) Glyceryl Oleate (and) Aluminum Stearate (and) Propylene Glycol (Dehymuls® F).
- the emulsifiers mentioned are commercial products from Cognis Deutschland GmbH, Düsseldorf. With regard to other suitable substances, reference is made to the chapter "Co-emulsifiers".
- the emulsifiers can be used in amounts of 1 to 20% by weight, based on the W / O emulsion.
- the polymerization of the monomers and co-monomers takes place in the emulsion in a manner known per se.
- an aqueous phase which is adjusted to an approximately neutral pH and which contains the monomers / co-monomers and stabilizers, radical initiators and the like, and an organic phase with the oil bodies and the W / O emulsifiers are usually prepared.
- the aqueous phase is added to the oil phase with strong shear and the W / O emulsion is prepared in this way.
- the polymerization then takes place at temperatures in the range from 40 to 60 ° C., which usually takes 3 to 10 and preferably 4 to 5 hours.
- the polymerized mass is then reacted at about 70 ° C. for about 1 h.
- a particular component of the process according to the invention is the phase inversion of water-in-oil after oil-in-water, which is caused by the polymerization of the monomers.
- Typical examples of this are optionally ethoxylated partial glycerides, e.g.
- Glyceryl stearate (Cutina® GMS) or PEG-20 glyceryl stearate (Cutina® E 24), fatty acids such as palmitic and stearic acid and their mixtures (Cutina® FS), ethoxylated oleyl or cetearyl alcohols with 5 to 30 EO units (Eumulgin® 0, Eumulgin® B) or adducts of 40 to 60 moles of ethylene oxide with hydroxy-substituted triglycerides, such as PEG-40 Hydrogenated Castor Oil (Eumulgin® HRE 40).
- Mixtures such as e.g.
- the emulsifiers mentioned are commercial products from Cognis Deutschland GmbH, Düsseldorf. With regard to other suitable substances, reference is made to the chapter "Co-emulsifiers”.
- the emulsifiers can be used in amounts of 1 to 20% by weight, based on the O / W emulsion.
- the cosmetic emulsions can be, for example, hair shampoos, hair lotions, foam baths, shower baths, creams, gels, lotions, alcoholic and aqueous / alcoholic solutions, emulsions, wax / fat masses, stick preparations or ointments.
- agents can also be used as further auxiliaries and additives, mild surfactants, co-emulsifiers, pearlescent waxes, consistency agents, thickeners, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, biogenic active ingredients, UV light protection factors, antioxidants, Contain deodorants, antiperspirants, antidandruff agents, film formers, swelling agents, insect repellents, self-tanners, tyrosine inhibitors (depigmenting agents), hydrotropes, solubilizers, preservatives, perfume oils, dyes and the like.
- surfactants mild surfactants, co-emulsifiers, pearlescent waxes, consistency agents, thickeners, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, biogenic active ingredients, UV light protection factors, antioxidants, Contain deodorants, antiperspirants, antid
- Anionic, nonionic, cationic and / or amphoteric or amphoteric surfactants can be present as surface-active substances, the proportion of these agents usually being about 1 to 70, preferably 5 to 50 and in particular 10 to 30% by weight.
- Typical examples of anionic surfactants are soaps, alkylbenzenesulfonates, alkanesulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids,
- Alkyl sulfates fatty alcohol ether sulfates, Glycerol ether, Fettklareethersulfate, hybrid droxymischethersulfate, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and salts thereof, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides , N-acylamino acids, such as acyl lactylates, acyl tartrates, acyl glutamates and acyl aspartates, alkyl oligoglucoside sulfates, protein fatty acid condensates (especially vegetable products based on wheat) and alkyl (ether) phosphates.
- anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
- Typical examples of 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 oligoglycosides, especially glucoronic acid, or glucoramic acid derivatives, and glucoronic acid nuclei (glucoronic acid) derivatives, in particular, glucoronic acid (G) -glucoronic acid (G) -glucoronic acid (G) -glucoric acid-derived (G) -glucoramic acid-derived (G) -glucoramic acid (G) -glucoric acid-derived (especially
- nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
- cationic surfactants are quaternary ammonium compounds, such as, for example, dimethyldistearylammonium chloride, and esterquats, in particular quaternized fatty acid trialkanolamine ester salts.
- amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The surfactants mentioned are exclusively known compounds.
- J.Falbe ed.
- Sudfactants in Consumer Products Springer Verlag, Berlin, 1987, pp. 54-124 or J.Falbe (ed.)
- Catalysts, surfactants and mineral oil additives Typical examples of particularly suitable mild, ie particularly skin-compatible surfactants are fatty alcohol polyglycol ether sulfates.
- suitable co-emulsifiers are 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) as well as cellulose ) with saturated and / or unsaturated, 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; > Mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol according to DE 1165574 PS and / or mixed esters of fatty acids with 6 to 22 carbon atoms, methyl glucose and polyols, preferably glycerol or polyglycerol.
- Block copolymers for example polyethylene glycol 30 dipolyhydroxystearate
- Polymer emulsifiers for example Pemulen types (TR-1, TR-2) from Goodrich
- 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 mixtures of homologs 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.
- C ⁇ 2 / ⁇ 8 - fatty acid monoesters and diesters of addition products of ethylene oxide with glycerol are known from DE 2024051 PS as refatting agents for cosmetic preparations.
- 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.
- 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 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.
- Suitable partial glycerides are hydroxystearic acid monoglyceride, hydroxystearic acid diglyceride, isostearic acid, Isostearinklarediglycerid, oleic acid monoglyceride, oleic acid diglyceride, Ricinolklaremoglycerid, Ricinolklarediglycerid, Linolklaremonoglycerid, Linolklarediglycerid, Linolenchuremonoglycerid, linolenic acid diglyceride, Erucaklaremonoglycerid, Erucaklakladiglycerid, Weinklaremonoglycerid, Weinklarediglycerid, Citronenklamonoglycerid, Citronendiglycerid, ⁇ pfelklamo- noglyceride, malic acid diglyceride and their technical mixtures, which may still contain minor amounts of triglyceride from the manufacturing process. Addition products of 1 to 30, preferably 5
- sorbitan sorbitan, sorbitan sesquiisostearate, sorbitan come diisostearate, sorbitan triisostearate, sorbitan monooleate, sorbitan dioleate, trioleate, Sorbitanmonoerucat, Sorbitansesquierucat, Sorbitandierucat, Sorbitantrierucat, Sorbitanmonoricinoleat, Sorbitansesquiricinoleat, Sorbitandiricinoleat, Sorbitantriricinoleat, Sorbitanmonohydroxystearat, Sorbitansesquihydroxystearat, sorbitan tandihydroxystearat, Sorbitantrihydroxystearat, Sorbitanmonotartrat , Sorbitan sesquitarate, sorbitan ditartrate, sorbitan tritartrate, sorbitan monocitrate, sorbitan sesquicitrate,
- Sorbitan citrate, sorbitan tricrate, sorbitan monomaleate, sorbitan sesquimaleate, sorbitan dimaleate, sorbitan trimaleate and their technical mixtures are possible. Addition products of 1 to 30, preferably 5 to 10, mol of ethylene oxide onto the sorbitan esters mentioned are also suitable.
- polyglycerol esters are polyglyceryl-2 dipolyhydroxystearates (Dehymuls® PGPH), polyglycerol-3-diisostearates (Lameform® TGI), polyglyceryl-4
- Isostearate (Isolan® GI 34), PolygIyceryl-3 Oleate, Diisostearoyl Polyglyceryl-3 Diisostearate (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 (Cre- mophor® GS 32) and Polyglyceryl Polyricinoleate (Admul® WOL 1403) Polyglyceryl Dimerate Isostearate and their mixtures , Examples of other suitable polyol esters are the mono-, di- and triesters of trimethylolpropane or pentaerythritol with lauric acid, coconut fatty acid, t
- Typical 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.
- Zwitterionic surfactants can also be used as emulsifiers.
- Zwitterionic surfactants are surface-active compounds that contain 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-carboxylm -3-hydroxyethylimidazolines 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 glyc
- Suitable emulsifiers are ampholytic surfactants.
- Ampholytic surfactants are surface-active compounds which, apart from a C8 / ⁇ 8 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -S0 3 H group and contain internal to form salts are capable.
- ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid, each with about 8 to 18 carbon atoms in the alkyl group. These are particularly preferred ampholytic surfactants
- N-Kokosalkylaminopropionat the Kokosacylaminoethylaminopropionat and the C ⁇ 2 ⁇ 8 - Acylsarcosin.
- cationic surfactants are also suitable as emulsifiers, those of the ester quat type, preferably methyl-quaternized difatty acid triethanolamine ester,
- Typical examples of fats are glycerides, i.e. Solid or liquid vegetable or animal products, which consist essentially of mixed glycerol esters of higher fatty acids, come as waxes, among others. natural waxes, e.g. Candelilla wax, camauba wax, japan wax, esparto grass wax, cork wax, guaruma wax, rice germ oil wax, sugar cane wax, ouricury wax, montan wax, beeswax, shellac wax, walrate, lanolin (wool wax), pretzel fat, ceresin, ozokerite (earth wax), petrolatum, paraffin waxes, microfax waxes chemically modified waxes (hard waxes), e.g.
- natural waxes e.g. Candelilla wax, camauba wax, japan wax, esparto grass wax, cork wax, guaruma wax, rice germ oil wax, sugar cane wax, ouricury wax, montan
- Montanester waxes Montanester waxes, Sasol waxes, hydrogenated jojoba waxes and synthetic waxes, such as Polyalkylene waxes and polyethylene glycol waxes in question.
- fat-like substances such as lecithins and phospholipids can also be used as additives.
- lecithins as those glycerophospholipids which are formed from fatty acids, glycerol, phosphoric acid and choline by esterification. Lecithins are therefore often used in the professional world as phosphatidylcholines (PC).
- 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 are: alkylene glycol esters, especially ethylene glycol stearate; 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, hydroxystearic 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 carbon atoms
- Suitable consistency agents are primarily fatty alcohols or hydroxy fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and, in addition, 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 Goodrich; Synthalene® from
- Bentonites such as e.g. Bentone® Gel VS-5PC (Rheox), which is a mixture of cyclopentasiloxane, disteardimonium hectorite and propylene carbonate.
- Surfactants such as, for example, ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as, for example, pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides and electrolytes such as sodium chloride and ammonium chloride are also suitable.
- Substances such as, for example, 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 magnesium, aluminum and / or zinc stearate or ricinoleate can be used as stabilizers.
- Suitable cationic polymers are, for example, cationic cellulose derivatives, e.g. a quaternized hydroxyethyl cellulose available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers such as e.g. Luviquat®
- BASF condensation products of polyglycols and amines, quaternized collagen polypeptides, such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, such as e.g. Amodimethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Chemviron), polyaminopolyamides, e.g.
- cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline, condensation products from dihaloalkylene, such as e.g. Dibromobutane with bisdialkylamines, e.g. Bis-dimethylamino-1,3-propane, cationic guar gum, e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese, quaternized ammonium salt polymers, e.g. Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol.
- dihaloalkylene such as e.g. Dibromobutane with bisdialkylamines, e.g. Bis-dimethylamino-1,3-propane
- cationic guar gum e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese
- quaternized ammonium salt polymers e.g. Mirapol
- 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 anhydride copolymers and polyesters and their esters, uncrosslinked , Acrylamido-propyltrimethylammonium chloride / acrylate copolymers, octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyvinyl pyrrolidone, vinyl pyrrolidone / vinyl acetate copolymers, vinyl pyrrolidone / teraminate / vinyl acrylate methacrylate / vinyl methacrylate methacrylate
- 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 in which there are are mixtures of dimethicones with an average chain length of 200 to 300 dimethylsiloxane units and hydrogenated silicates.
- suitable volatile silicones can also be found by Todd et al. in Cosm.Toil. 91, 27 (1976).
- UV light protection factors are understood to mean, for example, organic substances (light protection filters) which are liquid or crystalline at room temperature and which are able to absorb ultraviolet rays and absorb the energy absorbed in the form of longer-wave radiation, e.g. To give off heat again.
- UV-B filters can be oil-soluble or water-soluble. As oil-soluble substances e.g. to call:
- esters of salicylic acid preferably salicylic acid 2-ethylhexyl ester, salicylic acid 4-isopropylbenzyl ester, salicylic acid homomethyl ester; > Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4 "-methylbenzophenone, 2,2 x -dihydroxy-4-methoxybenzophenone;
- esters of benzalmalonic acid preferably 4-methoxybenzmalonic acid di-2-ethylhexyl ester;
- Triazine derivatives such as 2,4,6-TrianiIino- (p-carbo-2 ⁇ -ethyl- -hexyloxy) -l, 3,5-triazine and octyl triazone, as described in EP 0818450 AI or dioctyl butamido triazone
- Possible water-soluble substances are: > 2-phenylbenzimidazole-5-sulfonic acid and its alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium and glucammonium salts;
- Typical UV-A filters are, in particular, derivatives of benzoyl methane such as l- (4 ⁇ -tert.Butylphenyl) -3- (4-methoxyphenyl) propan-l, 3-dione, 4-tert-butyl -4 ⁇ - methoxydibenzoylmethane (Parsol® 1789), l-phenyl-3- (4 ⁇ - isopropylphenyl) propane-l, 3-dione and enamine compounds as described in DE 19712033 AI (BASF).
- the UV-A and UV-B filters can of course also be used in mixtures.
- Particularly favorable combinations consist of the derivatives of benzoyl methane, for example 4-tert-butyl 4 ⁇ methoxydibenzoylmethane (Parsol 1789) and 2-cyano-3,3-phenylcinnamate-2-ethyl-hexyl ester (Octocrylene), in combination with ester cinnamic acid, preferably 4-methoxycinnamic acid-2-ethylhexyl ester and / or 4-methoxycinnamic acid propyl ester and / or 4-methoxycinnamic acid isoamyl ester.
- benzoyl methane for example 4-tert-butyl 4 ⁇ methoxydibenzoylmethane (Parsol 1789) and 2-cyano-3,3-phenylcinnamate-2-ethyl-hexyl ester (Octocrylene)
- ester cinnamic acid preferably 4-methoxy
- 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 hydrophobicized.
- Typical examples are coated titanium dioxides, such as titanium dioxide T 805 (Degussa) or Eusolex® T2000 (Merck). 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 is preferably used. Further Suitable UV light protection filters are in the overview by P.Finkel in S ⁇ FW-Journal 122 f 543 (1996) and Parf.Kosm. 3, 11 (1999).
- secondary light stabilizers of the antioxidant type can also be used, which interrupt the photochemical reaction chain which is triggered when UV radiation penetrates the skin.
- amino acids e.g. glycine, histidine, tyrosine, tryptophan
- imidazoles e.g. urocanic acid
- peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g. Anserine), carotenoids, carotenes (e.g.
- Linoleyl, cholesteryl and glyceryl esters as well as their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g.
- buthioninsulfoximines homocysteine sulfoximine Hexa-, heptathioninsulfoximine
- very low tolerable doses eg pmol to ⁇ mol / kg
- metal chelators eg ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), ⁇ -hydroxy acids (eg citric acid, lactic acid, malic acid)
- ⁇ -hydroxy acids eg citric acid, lactic acid, malic acid
- Humic acid bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g. ⁇ -
- vitamin E acetate
- vitamin A and derivatives vitamin A palmitate
- biogenic active substances include tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, (deoxy) ribonucleic acid and its fragmentation products, ⁇ -glucans, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudo-ceramides, penal ceramides, Plant extracts, such as To understand prunus extract, Bambaranus extract and vitamin complexes.
- 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 which act as germ-inhibiting agents, enzyme inhibitors, odor absorbers or odor maskers.
- germ-inhibiting agents all substances effective against gram-positive bacteria are suitable as germ-inhibiting agents, such as.
- TTC antibacterial fragrances
- thymol thyme oil
- eugenol clove oil
- menthol eugenol
- mint oil eugenol
- famesol eugenol
- phenoxyethanol eugenol
- glycerol monocaprinate glycerol monocaprylate
- GML glycerol monolaurate
- DMC diglycerol monocaprinate
- B salicylic acid-n-octylamide or salicylic acid-n-decylamide.
- Esterase inhibitors are suitable as enzyme inhibitors. These are preferably trialkyl citrates such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and in particular triethyl citrate (Hydagen® CAT).
- the substances inhibit enzyme activity and thereby reduce odor.
- 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 acid, adipic acid acid, adipic acid acid, adipic acid, adipic acid, adipic acid, adipic acid - Ethyl ester, diethyl adipate, malonic acid and diethyl malonate, 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 s
- Suitable odor absorbers are substances that absorb odor-forming compounds and can retain them to a large extent. They lower the partial pressure of the individual components and thus also reduce their speed of propagation. It is important that perfumes must remain unaffected. Odor absorbers are not effective against bacteria. They contain, for example, a complex zinc salt of ricinoleic acid or special, largely odorless fragrances, which are known to the person skilled in the art as "fixators", such as, for example, the main component. B. extracts of Labdanum or Styrax or certain abietic acid derivatives. Fragrance agents or perfume oils act as odor maskers and, in addition to their function as odor maskers, give the deodorants their respective fragrance.
- Fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are e.g. Benzyl acetate, p-tert-butylcyclohexyl acetate, linalyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, allyl cyclohexyl propionate, styrallyl propionate and benzyl salicylate.
- the ethers include, for example, benzyl ethyl ether, the aldehydes e.g. the linear
- Alkanals with 8 to 18 carbon atoms citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal, for the ketones, for example the joonones and methylcedryl ketone, for the alcohols anethole, citronellol, eugenol, isoeugenol, geraniolethyl and linalool, phenolol, linalool ,
- the hydrocarbons mainly include the terpenes and balms. However, preference is given to using mixtures of different fragrances which together produce an appealing fragrance.
- perfume oils for example sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbane oil, labdanum oil and lavandin oil.
- Vertofix Coeur Iso-E-Super, Fixolide NP, Evernyl, Iraldein gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, Romilat, Irotyl and Floramat used alone or in mixtures.
- 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:
- Consistency adjuster > auxiliary substances 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.
- antiperspirants can contain customary oil-soluble and water-soluble auxiliaries in smaller amounts. Examples of such oil-soluble auxiliaries are: > anti-inflammatory, skin-protecting or fragrant essential oils,
- water-soluble additives are e.g. Preservatives, water-soluble fragrances, pH adjusting agents, e.g. Buffer mixtures, water soluble thickeners, e.g. water-soluble natural or synthetic polymers such as e.g. Xanthan gum, hydroxyethyl cellulose, polyvinyl pyrrolidone or high molecular weight polyethylene oxides.
- Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds.
- Piroctone olamine (1-hydroxy-4-methyl-6- (2,4,4-trimythylpentyl) -2- (1H) -pyridinone monoethanolamine salt
- Baypival® climbazole
- Ketoconazol® (4-acetyl) are used as anti-dandruff agents -l - ⁇ - 4- [2- (2.4-dichlorophenyl) r-2- (lH-imidazol-l-ylmethyl) -l, 3-dioxylan-c-4-ylmethoxyphenyljpiperazine, ketoconazole, elubiol, selenium disulfide, sulfur colloidal, Sulfur-polyethylene glycol sorbitan monooleate, sulfur ricinole polyhexoxide, sulfur tar distillates, salicylic acid (or in combination with hexachlorophene), undexylenic acid monoethanolamide sulfosuccinate sodium salt, Lamepon® UD (
- Possible insect repellents are N, N-diethyl-m-toluamide, 1,2-pentanediol or ethyl butyl acetylaminopropionate.
- Dihydroxyacetone is suitable as a self-tanner.
- Arbutin, ferulic acid, kojic acid, coumaric acid and ascorbic acid (vitamin C) can be used as tyrosine inhibitors, which prevent the formation of melanin and are used in depigmenting agents.
- Hydrotropes such as ethanol, isopropyl alcohol or polyols can also be used to improve the flow behavior.
- 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, hexylene 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;
- Dialcohol amines such as diethanolamine or 2-amino-l, 3-propanediol. preservative
- Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid, as well as the silver complexes known under the name Surfacine® and the other classes of substances listed in Appendix 6, Parts A and B of the Cosmetics Ordinance.
- Perfume oils include mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, cumin, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, calmus), woods (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme) ), Needles and twigs (spruce, fir, pine, mountain pine), resins and balsams (galbanum, elemi, benzoin, 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 e.g.
- the ethers include, for example, benzyl ethyl ether, the aldehydes e.g.
- Essential oils of lower volatility, 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. Bergamot oil, dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, ⁇ -hexylcinnamaldehyde, geraniol,
- Iso-E-Super Fixolide NP, Evernyl, Iraldein gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, Romilllat, Irotyl and Floramat used alone or in mixtures.
- suitable flavors are peppermint oil, spearmint oil, anise oil, stemanis oil, cumin oil, eucalyptus oil, fennel oil, lemon oil, wintergreen oil, clove oil, menthol and the like.
- the dyes which can be used are those substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. Examples are culinary red A (CI 16255), patent blue V (CI42051), indigo (CI73015), chlorophyllin (CI75810), quinoline yellow (CI47005), titanium dioxide (CI77891), indanthrene blue RS (CI 69800) and madder varnish (CI58000). Luminol may also be present as the luminescent dye. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
- 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; the phase inversion temperature method is preferably used.
- Example 1 300 g of deionized water and 500 g of concentrated acrylic acid were placed in a 2 l stirred vessel. Then the mixture was first added dropwise to a pH of 5.5 with ammonia solution and then with 0.5 g of sodium EDTA and 0.8 g of bisacrylamide. At the same time, an organic phase consisting of 200 g paraffin oil (Shellsol® D100) and 15 g sorbitan oleate (SPAN® 80) was produced in another mixing vessel. The organic phase was transferred to an Ultraturrax and the aqueous phase was slowly added over a period of 30 min at a stirring speed of 2500 rpm.
- Shellsol® D100 paraffin oil
- SPAN® 80 15 g sorbitan oleate
- the emulsion obtained in this way was then transferred to a polymerization reactor, flushed with nitrogen (500 ml / min) for 45 minutes and kept at 50 to 52 ° C. for 4 hours with the addition of 2 g of AIBN. After the polymerization was complete, the mass was heated at 70 ° C. for a further hour. Then allowed to cool to 30 ° C and the reaction product was mixed with 30 g castor oil + 40EO.
- the emulsion thus obtained had a solids content of 47% by weight and a Brookfield viscosity (25 ° C., 10 rpm) of 10,000 mPas.
- Example 2 Analogously to Example 1, 500 g of concentrated acrylic acid, 1 g of methyl methacrylate, 0.5 g of EDTA sodium salt and 25% by weight ammonia solution were combined until a pH of 5.5 was established.
- the organic phase was prepared by mixing 200 g of paraffin white oil and 15 g of oleic acid sorbitan ester (SPAN 80, ICI) with vigorous stirring. The organic phase was placed in an Ultraturrax and the aqueous phase was added over a period of 30 minutes at a speed of 3,500 rpm. The emulsion obtained in this way was then transferred to a polymerization reactor, flushed with nitrogen (700 ml / min) for 45 minutes and kept at 55 ° C.
- the emulsion thus obtained had a solids content of 44% by weight and a Brookfield viscosity (25 ° C., 10 rpm) of 8,000 mPas.
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Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2001295597A AU2001295597A1 (en) | 2000-10-17 | 2001-10-06 | Cosmetic emulsions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10051351A DE10051351A1 (de) | 2000-10-17 | 2000-10-17 | Kosmetische Emulsionen |
DE10051351.4 | 2000-10-17 |
Publications (2)
Publication Number | Publication Date |
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WO2002032380A2 true WO2002032380A2 (fr) | 2002-04-25 |
WO2002032380A3 WO2002032380A3 (fr) | 2002-07-18 |
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ID=7660040
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2001/011547 WO2002032380A2 (fr) | 2000-10-17 | 2001-10-06 | Emulsions cosmetiques |
Country Status (3)
Country | Link |
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AU (1) | AU2001295597A1 (fr) |
DE (1) | DE10051351A1 (fr) |
WO (1) | WO2002032380A2 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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DE102004027475B4 (de) * | 2004-06-02 | 2006-08-03 | Beiersdorf Ag | 2-Phenylethylbenzoat in kosmetischen Zubereitungen und die Verwendung zur Schaumverstärkung |
DE102004027477A1 (de) * | 2004-06-02 | 2005-12-29 | Beiersdorf Ag | 2-Phenylethylbenzoat in kosmetischen Öl-in-Wasser-UV-Lichtschutzemulsionen |
DE102004027476A1 (de) * | 2004-06-02 | 2005-12-22 | Beiersdorf Ag | 2-Phenylehtylbenzoat in kosmetischen Öl-in-Wasser-UV-Lichtschutzemulsionen |
DE102007052864A1 (de) * | 2007-11-02 | 2009-05-07 | Worlee-Chemie G.M.B.H. | Verdickungsmittel und dessen Anwendung |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4764574A (en) * | 1986-12-09 | 1988-08-16 | Phillips Petroleum Company | Inverse emulsion polymerization with sorbitan fatty acid esters and ethoxylated alcohol |
EP0503853A2 (fr) * | 1991-03-08 | 1992-09-16 | Scott Bader Company Limited | Agents épaississants polymères solubles dans l'eau pour produits pour l'application topique |
FR2773805A1 (fr) * | 1998-01-16 | 1999-07-23 | Seppic Sa | Nouveau latex epaississant, procede de fabrication et applications en cosmetique |
WO1999042521A1 (fr) * | 1998-02-17 | 1999-08-26 | Societe D'exploitation De Produits Pour Les Industries Chimiques (S.E.P.P.I.C.) | Polymere epaississant, procede de preparation et applications en cosmetique |
FR2785801A1 (fr) * | 1998-11-06 | 2000-05-19 | Seppic Sa | Nouveau latex inverse et utilisation en cosmetique |
EP1010708A1 (fr) * | 1998-12-18 | 2000-06-21 | Societe D'exploitation De Produits Pour Les Industries Chimiques, S.E.P.P.I.C. | Nouveau latex inverse stable aux électrolytes, procédé de préparation et utilisation en cosmétique |
EP1055707A1 (fr) * | 1999-05-28 | 2000-11-29 | Societe D'exploitation De Produits Pour Les Industries Chimiques, S.E.P.P.I.C. | Latex inverse auto inversible |
EP1152023A1 (fr) * | 2000-05-05 | 2001-11-07 | Societe D'exploitation De Produits Pour Les Industries Chimiques, S.E.P.P.I.C. | Latex inverses sur huiles blanches minérales, squalane ou polyisobutène hydrogéné, compositions cosmétiques, dermocosmétiques, dermopharmaceutiques ou pharmaceutiques en comportant |
FR2810545A1 (fr) * | 2000-06-23 | 2001-12-28 | Snf Sa | Utilisation comme epaississants en cosmetique de copolymeres neutralises comportant des motifs d'acides faible et des motifs d'acide fort, et compositions cosmetiques les contenant |
FR2810883A1 (fr) * | 2000-06-28 | 2002-01-04 | Seppic Sa | Nouveaux latex inverses autoinversibles sur des esters d'acides gras, compositions cosmetiques, dermocosmetiques, dermopharmaceutiques ou pharmaceutiques en comportant |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69934296T2 (de) * | 1998-01-16 | 2007-07-05 | Société d'Exploitation de Produits pour les Industries Chimiques-Seppic | Verdickend wirkendes latex, verfahren zu dessen herstellung und anwendungen in der kosmetik |
-
2000
- 2000-10-17 DE DE10051351A patent/DE10051351A1/de not_active Withdrawn
-
2001
- 2001-10-06 AU AU2001295597A patent/AU2001295597A1/en not_active Abandoned
- 2001-10-06 WO PCT/EP2001/011547 patent/WO2002032380A2/fr active Application Filing
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4764574A (en) * | 1986-12-09 | 1988-08-16 | Phillips Petroleum Company | Inverse emulsion polymerization with sorbitan fatty acid esters and ethoxylated alcohol |
EP0503853A2 (fr) * | 1991-03-08 | 1992-09-16 | Scott Bader Company Limited | Agents épaississants polymères solubles dans l'eau pour produits pour l'application topique |
FR2773805A1 (fr) * | 1998-01-16 | 1999-07-23 | Seppic Sa | Nouveau latex epaississant, procede de fabrication et applications en cosmetique |
WO1999042521A1 (fr) * | 1998-02-17 | 1999-08-26 | Societe D'exploitation De Produits Pour Les Industries Chimiques (S.E.P.P.I.C.) | Polymere epaississant, procede de preparation et applications en cosmetique |
FR2785801A1 (fr) * | 1998-11-06 | 2000-05-19 | Seppic Sa | Nouveau latex inverse et utilisation en cosmetique |
EP1010708A1 (fr) * | 1998-12-18 | 2000-06-21 | Societe D'exploitation De Produits Pour Les Industries Chimiques, S.E.P.P.I.C. | Nouveau latex inverse stable aux électrolytes, procédé de préparation et utilisation en cosmétique |
EP1055707A1 (fr) * | 1999-05-28 | 2000-11-29 | Societe D'exploitation De Produits Pour Les Industries Chimiques, S.E.P.P.I.C. | Latex inverse auto inversible |
EP1152023A1 (fr) * | 2000-05-05 | 2001-11-07 | Societe D'exploitation De Produits Pour Les Industries Chimiques, S.E.P.P.I.C. | Latex inverses sur huiles blanches minérales, squalane ou polyisobutène hydrogéné, compositions cosmétiques, dermocosmétiques, dermopharmaceutiques ou pharmaceutiques en comportant |
FR2810545A1 (fr) * | 2000-06-23 | 2001-12-28 | Snf Sa | Utilisation comme epaississants en cosmetique de copolymeres neutralises comportant des motifs d'acides faible et des motifs d'acide fort, et compositions cosmetiques les contenant |
FR2810883A1 (fr) * | 2000-06-28 | 2002-01-04 | Seppic Sa | Nouveaux latex inverses autoinversibles sur des esters d'acides gras, compositions cosmetiques, dermocosmetiques, dermopharmaceutiques ou pharmaceutiques en comportant |
Also Published As
Publication number | Publication date |
---|---|
AU2001295597A1 (en) | 2002-04-29 |
DE10051351A1 (de) | 2002-04-18 |
WO2002032380A3 (fr) | 2002-07-18 |
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