WO2007083184A2 - Cosmetic dermatology in acneic and comedogenic skin - Google Patents
Cosmetic dermatology in acneic and comedogenic skin Download PDFInfo
- Publication number
- WO2007083184A2 WO2007083184A2 PCT/IB2006/003579 IB2006003579W WO2007083184A2 WO 2007083184 A2 WO2007083184 A2 WO 2007083184A2 IB 2006003579 W IB2006003579 W IB 2006003579W WO 2007083184 A2 WO2007083184 A2 WO 2007083184A2
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- Prior art keywords
- skin
- acid
- formula
- pigment
- pigment according
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- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- FOYKKGHVWRFIBD-UHFFFAOYSA-N gamma-tocopherol acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 FOYKKGHVWRFIBD-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 1
- 239000013003 healing agent Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- KIUKXJAPPMFGSW-MNSSHETKSA-N hyaluronan Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H](C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-MNSSHETKSA-N 0.000 description 1
- 229940099552 hyaluronan Drugs 0.000 description 1
- 229920002674 hyaluronan Polymers 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000001524 infective effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 235000010213 iron oxides and hydroxides Nutrition 0.000 description 1
- 239000004407 iron oxides and hydroxides Substances 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- 238000010902 jet-milling Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 239000000978 natural dye Substances 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 230000037311 normal skin Effects 0.000 description 1
- 229960001679 octinoxate Drugs 0.000 description 1
- 230000037312 oily skin Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 229960001173 oxybenzone Drugs 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- MAMGRWPRCADEJL-UHFFFAOYSA-N phosphono octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OP(O)(O)=O MAMGRWPRCADEJL-UHFFFAOYSA-N 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000131 polyvinylidene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 229940055019 propionibacterium acne Drugs 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960000953 salsalate Drugs 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical class [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 229940045870 sodium palmitate Drugs 0.000 description 1
- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- SKIVFJLNDNKQPD-UHFFFAOYSA-N sulfacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 SKIVFJLNDNKQPD-UHFFFAOYSA-N 0.000 description 1
- 229960002673 sulfacetamide Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960000565 tazarotene Drugs 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical group OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052613 tourmaline Inorganic materials 0.000 description 1
- 239000011032 tourmaline Substances 0.000 description 1
- 229940070527 tourmaline Drugs 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical class O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- GAAKLDANOSASAM-UHFFFAOYSA-N undec-10-enoic acid;zinc Chemical compound [Zn].OC(=O)CCCCCCCCC=C GAAKLDANOSASAM-UHFFFAOYSA-N 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
- 229940088594 vitamin Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000010457 zeolite Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 229940118257 zinc undecylenate Drugs 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
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/28—Compounds of silicon
- C09C1/30—Silicic acid
- C09C1/3063—Treatment with low-molecular organic compounds
-
- 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
- A61K8/0241—Containing particulates characterized by their shape and/or structure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
-
- 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
- A61Q17/005—Antimicrobial 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/04—Compounds of zinc
- C09C1/043—Zinc oxide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/22—Compounds of iron
- C09C1/24—Oxides of iron
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/36—Compounds of titanium
- C09C1/3607—Titanium dioxide
- C09C1/3669—Treatment with low-molecular organic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/40—Compounds of aluminium
- C09C1/407—Aluminium oxides or hydroxides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/08—Treatment with low-molecular-weight non-polymer organic 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
- A61K2800/28—Rubbing or scrubbing compositions; Peeling or abrasive compositions; Containing exfoliants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/60—Particulates further characterized by their structure or composition
- A61K2800/61—Surface treated
- A61K2800/62—Coated
- A61K2800/622—Coated by organic compounds
Definitions
- the invention refers to pigments coated with anti-acne substances which afford the sustained release of said substances.
- the present invention also refers to a method to treat acneic and comedogenic skin through the use of a makeup comprising said pigments, wherein such use provides the immediate aesthetic relief (cover) the acneic imperfection underneath.
- the invention also refers to cosmetic compositions comprising said pigments.
- BACKGROUND OF THE INVENTION Surface-modified pigments and fillers for cosmetic applications were introduced to formulators in USA and Europe from Japan by Shoji Murata and Ryota Myoshi in 1981.
- filler pigments and colored pigments have been surface-treated with a variety of compounds to tailor-made their physico-chemical properties. Indeed, different performances are attained by each surface-modifier: silicones, metallic soaps, acyl amino acids, hydrogenated lecithin, collagen soaps, fluoro-carbons, fuoro-silicones, and so on.
- Surface-modified pigments have revolutionized the formulation of pressed powders, anhydrous foundations, blushers, and water-in-oil
- the "mixed" surface coating mentioned here utilizes an initial layer of coating on the pigment as a base on which an additional layer of coating is reacted. Though mixed coating consists of two different layers of chemical compounds, these two layers are synthesized (reacted) to be basically one compound that surrounds the base material.
- compositions contain saturated lipid and other ingredients which can be occlusive on skin pores, i.e. acting as comedogenic and/or favouring the formation of acne, particularly in oily skin of predisposed subjects.
- the term "comedogenic” describes the tendency of a topical preparation or material to induce the formation of sebum plugs (comedones) in the openings of sebaceous glands.
- the comedones undergo to inflammatory and infective processes which end up in the visible form of acne. This occurs when an increased sebum production accompanies a simultaneous blockage of the sebaceous gland openings. Then, the closed sebaceous glands become infected by anaerobic microorganisms such as Propionibacteria.
- the makeup industry is paying little if any attention to acneic and comedogenic skin, a condition prone to the acne degeneration by the infection of Propionibacteria - acnes or Corynebacterium acnes.
- pigments and topical compositions comprising thereof to treat acneic skin while providing an attractive makeup presentation, i.e. to improve the skin appearance with a concomitant effect of exfoliating/disinfecting action.
- the use of pigments in the manufacturing cosmetic/dermatologic composition comprising thereof can combat acneic skin on regular use, while immediately improving the skin appearance from the application of a cosmetic/dermatologic makeup.
- the invention also relates a method of manufacturing such pigment according to claims 27-29 and to a cosmetic/dermatologic product incorporating said pigment.
- the present invention also provide a method of prevention or treatment of acneic skin while improving the skin appearance, since the acneic imperfections are hidden.
- the pigments of invention comprise a pigment coated with anti-acne substances to promote their sustained release to afford the skin exfoliation and/or to disinfect skin and thus treat acneic skin.
- the pigments of the present invention have the following structure (I): wherein:
- C is a core pigment linked by a polyvalent cation M a the anion of a substance A capable to promote skin exfoliation and/or to disinfect skin, with the optional presence of bonded anionic surfactant B linked by a polyvalent cation M b .
- the b/a ratio ranges from 0 to about 10 w/w. According to another preferred embodiment, the b/a ratio ranges from about 0.1 to about 16 w/w, more preferably from about 1 to about 2 w/w.
- A ranges from 0.1% to 20% w/w on C, preferably 1 % to 4% w/w on C.
- M a and M b are preferably selected from: Zn 2+ , Cu 2+ , Ca 2+ , Ti 4+ , Si 4+ , Al 3+ , Sn 4+ , Mg 2+ , Sr 2+ , Ti 4+ , Zr 4+ , Ce 4+ , Fe 2+/3+ , Cr 6+ , and Mn 2+ ; more preferably selected from: Zn 2+ , Cu 2+ , Ca 2+ , Mg 2+ , and Al 3+ , even more preferably selected from: Zn 2+ , Ca 2+ , and Al 3+ .
- M a and M b are present at least in the quantity necessary to perform the linkage of a substance A and of the anionic surfactant B (when present) to C according to the formula (I).
- the pigments according the invention possess a core C (i.e. the pigment before being treated) consisting of pigments and pigment extenders of mean particle size from 3,000 ⁇ m to 0.001 ⁇ m, preferably from 20 ⁇ m to 0.01 ⁇ m.
- C as used herein include any pigment to be blended in cosmetics, including mixture and composite forms, e.g. those included in Rona catalogue (Merck, Darmstadt, D).
- Suitable Q include: titanium dioxide and oxide hydrated (TiO 2 , rutile and anatase, Ti(OH) 2 ), zinc oxide (ZnO), anhydrous and hydrated alumina (Al 2 O 3 , AlOOH), tin IV oxide (SnO 2 ), cerium oxide (CeO 4 ), and zirconium dioxide (ZrO 2 ), in sub-micron (1 - 0.1 ⁇ m) or in ultrafme forms (pigments having mean particle size ⁇ 0.1 ⁇ m)
- Suitable CU include: iron oxides and hydroxides such as FeO (yellow), Fe 2 O 3 and
- Fe 2 O 3 -H 2 O red
- Fe x O y brown
- Fe 3 O 4 black
- Suitable Q U include: mica (natural, synthetic, white, gold, red, black, and lithia micas), sericite, talc, kaolin, calcium and magnesium carbonate, calcium phosphate, alumina and aluminium hydroxide, magnesium oxide, barium sulfate, magnesium sulfate, silicic acid and silica, silicates (magnesium, aluminium, magnesium- aluminium silicate, calcium, and strontium silicates), silicon carbide, metal salts of tungstic acid, magnesium aluminate, magnesium metasilicate aluminate, chlorohydroxyaluminium, clay, bentonite, zeolite, smectite, hydroxyapatite, ceramic pigment, and boron nitride; specific composite extender pigments such as Excel Mica, Excel Pearl and Pigment La Vie (from Miyoshi Kasei, J), optically gloss pigments such as bismuth oxychloride, titanium mica, pearl essence, pigment prepared by coating synthetic
- MetashineTM Nippon Sheet Glass, J
- alumina flake with tin oxide and titanium dioxide or by coating aluminium flake with titanium dioxide, or by coating copper flake with silica, or by coating bronze flake with silica, or by coating aluminium flake with silica, or by coating coloring pigments (e.g. red iron oxide) with silica; other pigments such as luminescent pigment (e.g. LuminovaTM, Mitsui, J), aluminium and stainless pigment, tourmaline pigment, and amber pigment; etc.
- Suitable Q v include: tar pigment prepared into the form of lake, and naturally occurring dyes prepared into the form of lake such as Red No.s 3, 10, 106, 201, 202, 204, 205, 220, 226, 227, 228, 230, 401, 505, Yellow No.s 4, 5, Yellow 202, 203, 204, 401, Blue No.s 1, 2, 201, 404, Green No.s 3, 201, 204, 205, Orange No.s 201, 203, 204, 206, 207.
- Natural dyes lakes include pigments such as carmine, laccaic acid, carsamine, brazilin, and crocin. Further examples include hybrid pigments, e.g. those disclosed in our previous patents WO01/55262 and WO01/55263.
- Suitable C v include: cellulose fibres, wood dust, cotton fibres, starch, and synthetic microspheres, e.g. polyvinylidene/acrylonitrile copolymer, crossliked hyaluronan, powdered poly-lactate, powdered polyethylene, powdered nylon, powdered silicone, powdered polypropylene, powdered polycarbonate, powdered urea-formaldehyde resin, powdered crosslinked gelatin, powdered collagen, powdered keratin, powdered polystyrene and powdered Teflon.
- synthetic microspheres e.g. polyvinylidene/acrylonitrile copolymer, crossliked hyaluronan, powdered poly-lactate, powdered polyethylene, powdered nylon, powdered silicone, powdered polypropylene, powdered polycarbonate, powdered urea-formaldehyde resin, powdered crosslinked gelatin, powder
- the pigments according to the invention are basically formed of a core pigment C linked via one or more cation M a and M b to the anion of a substance A capable to promote skin exfoliation and/or to disinfect skin, thus treat acneic skin by the sustained release of said substance.
- Suitable A include: fumaric acid and monoester thereof, i.e. optionally esterified at a end-group by a Q.s-alkyl, e.g. mono-ethyl-fumarate, or an Aj ⁇ -ester, e.g. mono- salicyl-azelate.
- Preferred Ai are fumaric acid, and mono-ethyl fumarate.
- Suitable AU include: cysteine and derivatives include: L-cysteine itself and its derivatives, such as N-acetyl-cysteine, S-palmitoyl-cysteine, S-carboxymethyl- cysteine, methyl-S-carbamoyl-cysteine, S-acetamidomethyl-cysteine.
- Suitable AU also include: cysteine prodrugs, e.g. condensed cysteines having a 1,3- thiazolidine-4-carboxylate structure such as L-2-oxo-l,3-thiazolidine-4-carboxylic acid (“procysteine”), 2-(2-hydroxyphenyl)-l,3-thiazolidine-4-carboxylic acid, and the like.
- cysteine prodrugs e.g. condensed cysteines having a 1,3- thiazolidine-4-carboxylate structure such as L-2-oxo-l,3-thiazolidine-4-carboxylic acid (“procysteine”), 2-(2-hydroxyphenyl)-l,3-thiazolidine-4-carboxylic acid, and the like.
- Preferred A U are L-cysteine, N-acetyl-cysteine, S-carboxymethyl-cysteine, S- palmitoyl-cysteine, and procysteine.
- Suitable A;U include: benzoic acid; salicylic acid (2-hydroxybenzoic acid) and O- acyl- and O-aroyl-salicylates, e.g. acetyl salicylic acid ("ASA", or aspirin), salicyl salicylate, phenyl salicylate; and 5 -hydroxy-salicylates such as gentisic acid and ester thereof, e.g. 5-n-octanoylsalicylic acid.
- ASA acetyl salicylic acid
- phenyl salicylate phenyl salicylate
- 5 -hydroxy-salicylates such as gentisic acid and ester thereof, e.g. 5-n-octanoylsalicylic acid.
- Preferred A v are benzoic acid, salicylic acid, acetyl salicylic acid, benzyl salicylate, and gentisic acid.
- Suitable Aj V include: pyrithione (2-pyridinethiol 1 -oxide) and analogs thereof, e.g. those described by Doose C, in Green Chemistry, 2004, 259-266; and J. Chrom. A, 2004, 1052(1-2), 103-110.
- Preferred Aj V is pyrithione.
- Suitable A v include: include octopirox (l-hydroxy-4-methyl-6-(2,4,4- trimethylpentyl)-2(7H / )-pyridinone), ciclopirox (1 -hydroxy-4-methyl-6-cyclohexyl- 2(7H)-pyridmone) and analogs thereof, e.g. described in U.S. Pat. No. 6,455,551.
- Preferred A v are octopirox and ciclopirox.
- Suitable A v j include: tretinoin, (retinoic acid, ATRA, RA) and its isomers and equivalent, e.g. alitretinoin (9-cis-RA), isotretinoin (13-cis-RA), adapalene, bexarotene, fenretinide, acitretin, as well as free-carboxylic or free-phenolic containing arotinoids (e.g. TTNPB).
- the substances Aj- A v beside their capacity to promote skin exfoliation and/or to disinfect skin, have at least a carboxylic, phenolic or thiophenolic group which can be converted in anionic form.
- the anionic salt are soluble and/or dispersable in aqueous media, and this feature is of particularly use in the manufacturing steps carried out by ionic exchange either in wet-method (i.e. precipitation), or in semi-dry and dry-methods by ultra-mixing the solid powders, as further illustrated below.
- substances A;-A v may be present alone or in combination, or their intrinsic properties (e.g. texture, water repellency, dispersability, wear properties) can be further enhanced by the presence of hydrophobic and/or lipophilic substances.
- pigments of the invention may have a mixed layer comprising both A and B, the latter selected among an anionic surfactant capable of chelating M 3/ ),.
- Anionic surfactants suitable for the purpose of the invention are the commercially available anionic surfactants, sold either as salt or in non-ionized form.
- Suitable B include: carboxylate of formula 0 OOC-R; dicarboxylate of formula (" toOC-R'-COO"; ⁇ -hydroxycarboxylate of formula 0 OOC-CHR' -O-CO-R; alkylsuccinamate of formula 9 OOC-CH 2 CH 2 -O-CO-R ; N-alkanoyl-sarcosinate or - glycinate of formula 0 OOC-CH 2 -NR' -CO-R; N-acylglutamate or N-acylaspartate of formula (") OOC-CH 2 (CH 2 ) 0> i CH(NH-CO-R)-COO 0 ; and N ⁇ -acyl-lysinate of formula ⁇ OOC-CH(NH 2 )-(CH 2 ) 4 -NH-CO-R.
- Suitable Bui include: alkyl sulfonate of formula ⁇ - 1 O 3 S-R ; alkylsulfate of formula ⁇ O 3 S-O-R ; alkyl ester sulfonate of formula: ⁇ O 3 S-CHR-COOR'; alkyl amide sulfate of formula ⁇ OsSO-NHR'-CO-R ; alkyl-isethionate of formula: (2' ⁇ O 3 S- CH 2 CH 2 -CO-R ; N-acyl-N-alkyltaurate of formula (2") O 3 S-GH2CH 2 -NR'-CO-R; C 9 - C 20 -alkylbenzen-sulfonate; alkylsulfosuccinate of
- each -OR or -0-COR radical is a saturated or unsaturated, linear or branched, alkyl or acyl C 2 -C 22 , preferably C 8 -C 18 ; said R optionally comprising a polyalkoxy chain of formula -(OCH 2 CHR') Z -O- with z comprised between 1 and 100, preferably between 1 and 10; and each R' is H or C 1 -C 3 alkyl, preferably C 1 .
- Preferred -OR or -0OR radicals include those derived from caprylic, capric, lauric, myristic, palmitic, stearic, isostearic, palmitoleic, oleic, 12-hydroxystearic, 10- undecylenic, and ricinoleic acids and alcohols, alone or in combination, e.g. from vegetal sources.
- the dicarboxylate of formula H OOC-R'-COO H is a straight C 4-14 chains end- terminated with two carboxylic groups, e.g.
- saturated C 8-12 -dicarboxylic acid such as adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and dodecandioic acid unsaturated ⁇ , ⁇ -dicarboxylic acids such as straight C 4-14 chains end-terminated with two carboxylic groups, e.g. saturated C 8-12 -dicarboxylic acid such as adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and dodecandioic acid.
- Each B offers distinctive performances, e.g. increases holding moisture capacity; reduce stickiness, increase spreading; enhances smooth feel and skin adhesion; increases refreshment and smoothness to cosmetic/dermatologic makeup.
- the substances A and the optional surfactants B are employed as alkaline salts (e.g. sodium and potassium salts) or ammonium salts (e.g. ammonium and DEA salts) to facilitate water dispersion and the ionic exchange with polyvalent cations.
- alkaline salts e.g. sodium and potassium salts
- ammonium salts e.g. ammonium and DEA salts
- Suitable polyvalent cations are selected among water soluble salts, e.g. sulfates, nitrates, chlorides and acetates of polyvalent cations including Zn 2+ , Cu 2+ , Ca 2+ , Ti 4+ ,
- B is comprised up to 8% w/w on C.
- the process of manufacturing the pigments of invention can either be carried out in wet/slurried form, wherein core pigment C is suspended in water and treated until the desired coating is attained; or in dry or semi-dry conditions, e.g. by high-intensity agitation, high-impact mixing, or a combination of these methods.
- a general wet method is attained by ion-exchange in water of one or more A, or by the simultaneous or the sequential coating of A and B via ion-exchange.
- a preferred wet method is the reaction onto the core pigments C suspended in water with one or more water-soluble multivalent cation(s), then with the slurry is reacted with an alkaline solution of A, optionally in the presence of B, as described in the Example.
- Another preferred method is the direct precipitation.
- the core pigments C are suspended in a solution of the alkaline salts of the substances A (and B if desired), then precipitation is carried out by the addition of a solution of the water- soluble salt of the polyvalent cation(s).
- An illustrative example of this procedure comprises the formation of an alkaline solution of substances A (and B if desired), and Na or K aluminate or zincate.
- the core pigment C is then suspended into the alkaline solution and brought to a pH between 9.5-10.5 by adding a mineral acid.
- the system is then neutralized with acidic polyvalent cation(s) and/or mineral acid.
- a further example of co-precipitation comprises the pre-coating with Zn 2+ , Cu 2+ or alkaline-earthy oxide-hydroxides, formed by suspending the core pigment C into water, heating at 40-90°C, followed adding an acidic salt of a polyvalent cation. Simultaneously, a mineral alkali or acid is added to keep pH 5-to-9 until precipitation takes place, then substance A (and B if desired) is precipitated by an acidic salt of the polyvalent cation(s).
- Another preferred method is the dry or semi-dry coating of the core pigment C, which is carried out under high-intensity agitation or high-impact mixing of the powdered C with the substances A (and B if desired) in dry or "semi-dry" manner.
- the latter means that A (and B if desired) are sprayed onto C as concentrated (e.g. alkaline or solvent) solutions.
- This method applies to core pigments C comprising, or at least are surface-treated with, a metal oxide and hydroxide, since the cationic bridge C-M a -A (and C-M b -B) is formed at high temperature in situ by ion exchange of A (and B) in acidic form or as alkaline salt.
- the pigments of invention can be produced by further well-known coating techniques which with only minor modifications to the overall features of the present invention.
- the aqueous slurry obtained by a wet method can be dried up by several drying methods, e.g. filtration and grinding, spray drying, jet-milling or fluidized bed drying.
- the slurry may be washed up from the salts and the pigments can be used directly to manufacture the cosmetic/dermatologic compositions as suspensions, optionally with 0.1-10% added dispersant(s) to stabilize them on storage (before use).
- the present invention refers to a method of treatment of acneic skin by the use of said pigments in cosmetic/dermatologic compositions.
- Acneic skin types have more oil-producing sebaceous follicles with little, if any, hair in them. This means the oily waste inside the follicle builds up because there's nothing to act as a transport system out of the skin. The sebum produced also is thicker and stickier in acneic skin types. Acneic skin produces 4-to-5 times more skin cells inside of the follicle than normal skin, so that the follicle tends to occlude because the skin does not exfoliate at sufficient high rate. When follicles fill with excess oil from the sebaceous glands and an accumulation of dead cells, a favourable environment for bacteria is created. Blackheads form and create a blockage at the mouth of the follicle. The follicles swell and rupture, causing the debris to escape into skin, irritating it and producing an inflamed red bump.
- the method of the invention afford the prevention or treatment of acneic skin with the regular use of a makeup composition comprising the pigment of invention, while these also beautify the skin and hidden the acneic imperfection underneath.
- the invention refers to cosmetic/dermatological compositions comprising the pigments described above.
- compositions according to the invention may also comprise any cosmetically acceptable ingredients, and can be associated with other components with auxiliary action in the treatment and prevention of acne or providing skin benefits.
- additional components are, for instance, other ingredients active against proliferation of Propionibacterium acnes, e. g. antibiotics such as erythromycin, clindamycin and tetracyclines; antimicrobials such as chlorexidine and benzoylperoxide, synthetic or natural substances described as possessing inhibitory activity against P. acnes such as 1-pentadecanol and derivatives thereof, cedrene, caryophyllene, and longifolene; retinoids other-than-tretinoin such as adapalene, tazarotene, etc.; NSAID antinflammatory agents such as ibuprofen, naproxen, sulfacetamide; steroidal antinflammatory agents (e. g. hydrocortisone); vitamins; skin healing agents; and skin conditioners.
- antibiotics such as erythromycin, clindamycin and tetracyclines
- antimicrobials such as chlorexidine and benzoylperoxide, synthetic or natural substances described as possessing
- Aj-A v substances itself, in the sense that, one or more of Aj- A v can be present both in form of C-bonded and dispersed (unbonded) form, i.e. admixed into the composition by physical means, hi this way the composition according to the invention afford both immediate and sustained release of As.
- the pigments of the invention can be employed alone or in combination with others other non-coated or differently coated pigment, as well as nacres and/or fillers in makeup and sun protection compositions in any amounts between 0.1 and 80 % by weight or more.
- the cosmetic/dermatologic comprising the pigment of the invention includes, for example, makeup cosmetics such as powder foundation, liquid foundation, cream foundation, oily foundation, stick foundation, pressed powder, face powder; lipstick, rouge; eye shadow, pencil, and liner; mascara; fundamental cosmetics such as emollient cream, emollient lotion, milky lotion, massage lotion, cold cream, whitening cream, emulsion, lotion, aesthetic lotion, carmine lotion; cleansing cosmetic/dermatologic for makeup, cleansing jell, liquid wash, washing foam, washing cream, washing powder; and others including cream and emulsions for sun screening and sun tanning.
- Preferred cosme-dermatologic compositions are the foundations in different form, and the fundamental cosmetics as listed herein.
- composition comprising the pigments of invention and of the curative method of invention are:
- composition of invention may appropriately be compounded, e.g. with pigment dispersants, oils, surfactants, UV absorbents, preservatives, anti- oxidants, film forming agents, emollient agents, thickeners, dyes, and fragrance within a broad range with further advantages of the inventive purposes.
- Example B Semi-dry method
- the amount of the water-soluble multivalent cation salt and the caustic soda can be adjusted according to the amount of A (and B) used.
- a (and B) in the form of alkaline salts are soluble and/or dispersible at room temperature, then the coating is carried out without warming; whilst the temperature is brought to 75-80°C when at least one of A and/or B not dissolves in water but as melted form (e.g. sodium palmitate).
- a fatty blend is produced by mixing waxes and oils at 80°C with stirring until a homogeneous mixture is obtained.
- the pigments and fillers are added always at 80°C and with stirring until a homogeneous color is obtained.
- the remainder of the components are added and the temperature is maintained at 80°C for 2 hours with stirring.
- the resulting foundations have the following compositions:
- the emulsion contains: Glycerin 87% 3.0g
- grade 0 no comedones or papules but an history of recurring acne
- grade I a few to moderate comedones + a few papules
- grade II a few to moderate papules + a few pustules
- grade III a few to moderate pustules + nodule/cyst and scarring.
- the subjects are given the Applicative Examples 1 or 2 or 3 according to their skin hues, to be applied on regular daily base as decorative foundation.
- the volunteers are assessed for the baseline and at the end of week 1, 2, 4, and 6.
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Abstract
Curative pigments sustained release exfoliating, disinfecting and anti-androgenetic substances are suitable for the dermatologic makeup, optionally in the presence of hydrophobic surfactant to provide products with improved skin feel. Makeup compositions with these pigments are indicated for the immediate aesthetic relief the acneic imperfection underneath, while they smoothly carry out a beneficial treatment of acneic and comedogenic skin by releasing anti-acne agents.
Description
COSMETIC DERMATOLOGY IN ACNEIC AND COMEDOGENIC SKIN
FIELD OF THE INVENTION
The invention refers to pigments coated with anti-acne substances which afford the sustained release of said substances. The present invention also refers to a method to treat acneic and comedogenic skin through the use of a makeup comprising said pigments, wherein such use provides the immediate aesthetic relief (cover) the acneic imperfection underneath.
The invention also refers to cosmetic compositions comprising said pigments. BACKGROUND OF THE INVENTION Surface-modified pigments and fillers for cosmetic applications were introduced to formulators in USA and Europe from Japan by Shoji Murata and Ryota Myoshi in 1981.
Afterwards, filler pigments and colored pigments have been surface-treated with a variety of compounds to tailor-made their physico-chemical properties. Indeed, different performances are attained by each surface-modifier: silicones, metallic soaps, acyl amino acids, hydrogenated lecithin, collagen soaps, fluoro-carbons, fuoro-silicones, and so on. Surface-modified pigments have revolutionized the formulation of pressed powders, anhydrous foundations, blushers, and water-in-oil
(or -silicone) foundations by providing enhanced skin feel, formula stability, texture, dispersibility, and wear properties.
One unique approach is the mixed surface coatings. The "mixed" surface coating mentioned here utilizes an initial layer of coating on the pigment as a base on which an additional layer of coating is reacted. Though mixed coating consists of two different layers of chemical compounds, these two layers are synthesized (reacted) to be basically one compound that surrounds the base material.
Different from hybrid surface coatings, multiple layered surface coatings are recently beginning to gain attention, also provides similar potentials and benefits.
However, many commercially available makeup compositions contain saturated lipid and other ingredients which can be occlusive on skin pores, i.e. acting as comedogenic and/or favouring the formation of acne, particularly in oily skin of predisposed subjects.
The term "comedogenic" describes the tendency of a topical preparation or material to induce the formation of sebum plugs (comedones) in the openings of sebaceous glands. The comedones undergo to inflammatory and infective processes which end up in the visible form of acne. This occurs when an increased sebum production accompanies a simultaneous blockage of the sebaceous gland openings. Then, the closed sebaceous glands become infected by anaerobic microorganisms such as Propionibacteria.
The makeup industry is paying little if any attention to acneic and comedogenic skin, a condition prone to the acne degeneration by the infection of Propionibacteria - acnes or Corynebacterium acnes.
Instead, there is a need for pigments and topical compositions comprising thereof to treat acneic skin while providing an attractive makeup presentation, i.e. to improve the skin appearance with a concomitant effect of exfoliating/disinfecting action. SUMMARY OF THE INVENTION It has been discovered that a pigment coated with substances capable to promote skin exfoliation and/or to disinfect skin by the sustained release of said substances.
Hence, the use of pigments in the manufacturing cosmetic/dermatologic composition comprising thereof can combat acneic skin on regular use, while immediately improving the skin appearance from the application of a cosmetic/dermatologic makeup.
The above aim is reached by means of the present invention, that relates to a pigment according to claim 1.
The invention also relates a method of manufacturing such pigment according to claims 27-29 and to a cosmetic/dermatologic product incorporating said pigment. The present invention also provide a method of prevention or treatment of acneic skin while improving the skin appearance, since the acneic imperfections are hidden. DETAILED DESCRIPTION OF THE INVENTION
The pigments of invention comprise a pigment coated with anti-acne substances to promote their sustained release to afford the skin exfoliation and/or to disinfect skin and thus treat acneic skin. hi detail, the pigments of the present invention have the following structure (I):
wherein:
C is a core pigment linked by a polyvalent cation Ma the anion of a substance A capable to promote skin exfoliation and/or to disinfect skin, with the optional presence of bonded anionic surfactant B linked by a polyvalent cation Mb.
According to a preferred embodiment, the b/a ratio ranges from 0 to about 10 w/w. According to another preferred embodiment, the b/a ratio ranges from about 0.1 to about 16 w/w, more preferably from about 1 to about 2 w/w.
According to a preferred embodiment, A ranges from 0.1% to 20% w/w on C, preferably 1 % to 4% w/w on C.
Ma and Mb are preferably selected from: Zn2+, Cu2+, Ca2+, Ti4+, Si4+, Al3+, Sn4+, Mg2+, Sr2+, Ti4+, Zr4+, Ce4+, Fe2+/3+, Cr6+, and Mn2+; more preferably selected from: Zn2+, Cu2+, Ca2+, Mg2+, and Al3+, even more preferably selected from: Zn2+, Ca2+, and Al3+. Ma and Mb are present at least in the quantity necessary to perform the linkage of a substance A and of the anionic surfactant B (when present) to C according to the formula (I).
The pigments according the invention possess a core C (i.e. the pigment before being treated) consisting of pigments and pigment extenders of mean particle size from 3,000 μm to 0.001 μm, preferably from 20 μm to 0.01 μm.
C as used herein include any pigment to be blended in cosmetics, including mixture and composite forms, e.g. those included in Rona catalogue (Merck, Darmstadt, D).
Suitable Q include: titanium dioxide and oxide hydrated (TiO2, rutile and anatase, Ti(OH)2), zinc oxide (ZnO), anhydrous and hydrated alumina (Al2O3, AlOOH), tinIV oxide (SnO2), cerium oxide (CeO4), and zirconium dioxide (ZrO2), in sub-micron (1 - 0.1 μm) or in ultrafme forms (pigments having mean particle size < 0.1 μm)
Suitable CU include: iron oxides and hydroxides such as FeO (yellow), Fe2O3 and
Fe2O3-H2O (red), FexOy (brown), Fe3O4 (black); chromium oxides and hydroxides
(Cr2O3.nH2O and Cr2O3); tin11 oxide (SnO), manganese oxide (MnO), Prussian blue, ultramarine blue, inorganic blue pigments, low order Ti oxides, mango and cobalt violets.
Suitable QU include: mica (natural, synthetic, white, gold, red, black, and lithia micas), sericite, talc, kaolin, calcium and magnesium carbonate, calcium phosphate, alumina and aluminium hydroxide, magnesium oxide, barium sulfate, magnesium sulfate, silicic acid and silica, silicates (magnesium, aluminium, magnesium- aluminium silicate, calcium, and strontium silicates), silicon carbide, metal salts of tungstic acid, magnesium aluminate, magnesium metasilicate aluminate, chlorohydroxyaluminium, clay, bentonite, zeolite, smectite, hydroxyapatite, ceramic pigment, and boron nitride; specific composite extender pigments such as Excel Mica, Excel Pearl and Pigment La Vie (from Miyoshi Kasei, J), optically gloss pigments such as bismuth oxychloride, titanium mica, pearl essence, pigment prepared by coating synthetic mica with titanium dioxide, or by coating silica flake with titanium dioxide (e.g. Metashine™; Nippon Sheet Glass, J), or by coating alumina flake with tin oxide and titanium dioxide, or by coating aluminium flake with titanium dioxide, or by coating copper flake with silica, or by coating bronze flake with silica, or by coating aluminium flake with silica, or by coating coloring pigments (e.g. red iron oxide) with silica; other pigments such as luminescent pigment (e.g. Luminova™, Mitsui, J), aluminium and stainless pigment, tourmaline pigment, and amber pigment; etc.
Suitable Qv include: tar pigment prepared into the form of lake, and naturally occurring dyes prepared into the form of lake such as Red No.s 3, 10, 106, 201, 202, 204, 205, 220, 226, 227, 228, 230, 401, 505, Yellow No.s 4, 5, Yellow 202, 203, 204, 401, Blue No.s 1, 2, 201, 404, Green No.s 3, 201, 204, 205, Orange No.s 201, 203, 204, 206, 207. Natural dyes lakes include pigments such as carmine, laccaic acid, carsamine, brazilin, and crocin. Further examples include hybrid pigments, e.g. those disclosed in our previous patents WO01/55262 and WO01/55263.
Suitable Cv include: cellulose fibres, wood dust, cotton fibres, starch, and synthetic
microspheres, e.g. polyvinylidene/acrylonitrile copolymer, crossliked hyaluronan, powdered poly-lactate, powdered polyethylene, powdered nylon, powdered silicone, powdered polypropylene, powdered polycarbonate, powdered urea-formaldehyde resin, powdered crosslinked gelatin, powdered collagen, powdered keratin, powdered polystyrene and powdered Teflon.
The pigments according to the invention are basically formed of a core pigment C linked via one or more cation Ma and Mb to the anion of a substance A capable to promote skin exfoliation and/or to disinfect skin, thus treat acneic skin by the sustained release of said substance. Suitable A; include: fumaric acid and monoester thereof, i.e. optionally esterified at a end-group by a Q.s-alkyl, e.g. mono-ethyl-fumarate, or an Ajϋ-ester, e.g. mono- salicyl-azelate.
Preferred Ai are fumaric acid, and mono-ethyl fumarate.
Suitable AU include: cysteine and derivatives include: L-cysteine itself and its derivatives, such as N-acetyl-cysteine, S-palmitoyl-cysteine, S-carboxymethyl- cysteine, methyl-S-carbamoyl-cysteine, S-acetamidomethyl-cysteine.
Suitable AU also include: cysteine prodrugs, e.g. condensed cysteines having a 1,3- thiazolidine-4-carboxylate structure such as L-2-oxo-l,3-thiazolidine-4-carboxylic acid ("procysteine"), 2-(2-hydroxyphenyl)-l,3-thiazolidine-4-carboxylic acid, and the like.
Preferred AU are L-cysteine, N-acetyl-cysteine, S-carboxymethyl-cysteine, S- palmitoyl-cysteine, and procysteine.
Suitable A;U include: benzoic acid; salicylic acid (2-hydroxybenzoic acid) and O- acyl- and O-aroyl-salicylates, e.g. acetyl salicylic acid ("ASA", or aspirin), salicyl salicylate, phenyl salicylate; and 5 -hydroxy-salicylates such as gentisic acid and ester thereof, e.g. 5-n-octanoylsalicylic acid.
Preferred Av are benzoic acid, salicylic acid, acetyl salicylic acid, benzyl salicylate, and gentisic acid.
Suitable AjV include: pyrithione (2-pyridinethiol 1 -oxide) and analogs thereof, e.g. those described by Doose C, in Green Chemistry, 2004, 259-266; and J. Chrom. A, 2004, 1052(1-2), 103-110.
Preferred AjV is pyrithione.
Suitable Av include: include octopirox (l-hydroxy-4-methyl-6-(2,4,4- trimethylpentyl)-2(7H/)-pyridinone), ciclopirox (1 -hydroxy-4-methyl-6-cyclohexyl- 2(7H)-pyridmone) and analogs thereof, e.g. described in U.S. Pat. No. 6,455,551. Preferred Av are octopirox and ciclopirox.
Suitable Avj include: tretinoin, (retinoic acid, ATRA, RA) and its isomers and equivalent, e.g. alitretinoin (9-cis-RA), isotretinoin (13-cis-RA), adapalene, bexarotene, fenretinide, acitretin, as well as free-carboxylic or free-phenolic containing arotinoids (e.g. TTNPB). The substances Aj- Av, beside their capacity to promote skin exfoliation and/or to disinfect skin, have at least a carboxylic, phenolic or thiophenolic group which can be converted in anionic form. The anionic salt are soluble and/or dispersable in aqueous media, and this feature is of particularly use in the manufacturing steps carried out by ionic exchange either in wet-method (i.e. precipitation), or in semi-dry and dry-methods by ultra-mixing the solid powders, as further illustrated below. hi the pigments according to the invention, substances A;-Av, may be present alone or in combination, or their intrinsic properties (e.g. texture, water repellency, dispersability, wear properties) can be further enhanced by the presence of hydrophobic and/or lipophilic substances. Accordingly, pigments of the invention may have a mixed layer comprising both A and B, the latter selected among an anionic surfactant capable of chelating M3/),.
Anionic surfactants suitable for the purpose of the invention are the commercially available anionic surfactants, sold either as salt or in non-ionized form.
Suitable B; include: carboxylate of formula 0OOC-R; dicarboxylate of formula (" toOC-R'-COO"; α-hydroxycarboxylate of formula 0OOC-CHR' -O-CO-R; alkylsuccinamate of formula 9OOC-CH2CH2-O-CO-R ; N-alkanoyl-sarcosinate or - glycinate of formula 0OOC-CH2-NR' -CO-R; N-acylglutamate or N-acylaspartate of formula (")OOC-CH2(CH2)0>i CH(NH-CO-R)-COO0 ; and Nε-acyl-lysinate of formula ΘOOC-CH(NH2)-(CH2)4-NH-CO-R. Suitable Bj1 include: alkyl- or dialkyl-phosphate of formula: (")OaP(O)-(OR)b; wherein a=l or 2; and b=3-a.
Suitable Bui include: alkyl sulfonate of formula ^-1O3S-R ; alkylsulfate of formula ^O3S-O-R ; alkyl ester sulfonate of formula: ^O3S-CHR-COOR'; alkyl amide sulfate of formula ^OsSO-NHR'-CO-R ; alkyl-isethionate of formula: (2'}O3S- CH2CH2-CO-R ; N-acyl-N-alkyltaurate of formula (2")O3S-GH2CH2-NR'-CO-R; C9- C20-alkylbenzen-sulfonate; alkylsulfosuccinate of formula ^OsS-CHtCOORO-CH^ R sulfosuccinate monoesters or diesters; alkylglycosides sulphate, and the like. hi Bj-Bjjj, each -OR or -0-COR radical is a saturated or unsaturated, linear or branched, alkyl or acyl C2-C22, preferably C8-C18; said R optionally comprising a polyalkoxy chain of formula -(OCH2CHR')Z-O- with z comprised between 1 and 100, preferably between 1 and 10; and each R' is H or C1-C3 alkyl, preferably C1.
Preferred -OR or -0OR radicals include those derived from caprylic, capric, lauric, myristic, palmitic, stearic, isostearic, palmitoleic, oleic, 12-hydroxystearic, 10- undecylenic, and ricinoleic acids and alcohols, alone or in combination, e.g. from vegetal sources. In Bj the dicarboxylate of formula HOOC-R'-COOH is a straight C4-14 chains end- terminated with two carboxylic groups, e.g. saturated C8-12-dicarboxylic acid such as adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and dodecandioic acid unsaturated α,τσ-dicarboxylic acids such as straight C4-14 chains end-terminated with two carboxylic groups, e.g. saturated C8-12-dicarboxylic acid such as adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and dodecandioic acid.
Each B offers distinctive performances, e.g. increases holding moisture capacity; reduce stickiness, increase spreading; enhances smooth feel and skin adhesion; increases refreshment and smoothness to cosmetic/dermatologic makeup.
Preferably the substances A and the optional surfactants B are employed as alkaline salts (e.g. sodium and potassium salts) or ammonium salts (e.g. ammonium and DEA salts) to facilitate water dispersion and the ionic exchange with polyvalent cations.
Suitable polyvalent cations are selected among water soluble salts, e.g. sulfates, nitrates, chlorides and acetates of polyvalent cations including Zn2+, Cu2+, Ca2+, Ti4+,
Si4+, Al3+, Sn4+, Mg2+, Sr2+, Ti4+, Zr4+, Ce4+, Fe2+/3+, Cr6+ , Mn2+, and mixture thereof; or amphoteric salts of Zn2+, Ti4+, Al3+, Si4+ such as Na or K zincate, titanate, aluminate, and silicate.
According to another preferred embodiment, B is comprised up to 8% w/w on C.
As for the process of manufacturing the pigments of invention, it can either be carried out in wet/slurried form, wherein core pigment C is suspended in water and treated until the desired coating is attained; or in dry or semi-dry conditions, e.g. by high-intensity agitation, high-impact mixing, or a combination of these methods.
A general wet method is attained by ion-exchange in water of one or more A, or by the simultaneous or the sequential coating of A and B via ion-exchange.
A preferred wet method is the reaction onto the core pigments C suspended in water with one or more water-soluble multivalent cation(s), then with the slurry is reacted with an alkaline solution of A, optionally in the presence of B, as described in the Example.
Another preferred method is the direct precipitation. In this case the core pigments C are suspended in a solution of the alkaline salts of the substances A (and B if desired), then precipitation is carried out by the addition of a solution of the water- soluble salt of the polyvalent cation(s).
Further preferred wet methods is based on co-precipitation. An illustrative example of this procedure comprises the formation of an alkaline solution of substances A (and B if desired), and Na or K aluminate or zincate. The core pigment C is then suspended into the alkaline solution and brought to a pH between 9.5-10.5 by adding a mineral acid. The system is then neutralized with acidic polyvalent cation(s) and/or mineral acid.
A further example of co-precipitation comprises the pre-coating with Zn2+, Cu2+ or alkaline-earthy oxide-hydroxides, formed by suspending the core pigment C into water, heating at 40-90°C, followed adding an acidic salt of a polyvalent cation. Simultaneously, a mineral alkali or acid is added to keep pH 5-to-9 until precipitation takes place, then substance A (and B if desired) is precipitated by an acidic salt of the polyvalent cation(s).
Another example is the reaction on C of amphoteric salts of multivalent cation(s) or alkaline-earthy hydroxides (e.g. Ca(OH)2) and a alkaline solution of substances A (and B if desired), followed by neutralization acidic polyvalent cation(s) and/or mineral acid.
Other examples of wet precipitation may be carried out by suspending substances A (and B if desired) in neutral or slightly acidic water under heating, e.g. 70°-95°C. This suspension is added with the core pigment C and stirred until at least part of substances A (and B if desired) are absorbed onto C. The water-soluble salts of multivalent cation(s) are then admixed under stirring, the slurry is heated and stirred, eventually neutralized.
Another preferred method is the dry or semi-dry coating of the core pigment C, which is carried out under high-intensity agitation or high-impact mixing of the powdered C with the substances A (and B if desired) in dry or "semi-dry" manner. The latter means that A (and B if desired) are sprayed onto C as concentrated (e.g. alkaline or solvent) solutions.
This method applies to core pigments C comprising, or at least are surface-treated with, a metal oxide and hydroxide, since the cationic bridge C-Ma-A (and C-Mb-B) is formed at high temperature in situ by ion exchange of A (and B) in acidic form or as alkaline salt.
The pigments of invention can be produced by further well-known coating techniques which with only minor modifications to the overall features of the present invention.
Noteworthy, the aqueous slurry obtained by a wet method can be dried up by several drying methods, e.g. filtration and grinding, spray drying, jet-milling or fluidized bed drying. Alternatively, the slurry may be washed up from the salts and the pigments can be used directly to manufacture the cosmetic/dermatologic compositions as suspensions, optionally with 0.1-10% added dispersant(s) to stabilize them on storage (before use). According to another aspect, the present invention refers to a method of treatment of acneic skin by the use of said pigments in cosmetic/dermatologic compositions.
Acneic skin types have more oil-producing sebaceous follicles with little, if any, hair in them. This means the oily waste inside the follicle builds up because there's nothing to act as a transport system out of the skin. The sebum produced also is thicker and stickier in acneic skin types. Acneic skin produces 4-to-5 times more skin cells inside of the follicle than normal skin, so that the follicle tends to occlude
because the skin does not exfoliate at sufficient high rate. When follicles fill with excess oil from the sebaceous glands and an accumulation of dead cells, a favourable environment for bacteria is created. Blackheads form and create a blockage at the mouth of the follicle. The follicles swell and rupture, causing the debris to escape into skin, irritating it and producing an inflamed red bump.
The method of the invention afford the prevention or treatment of acneic skin with the regular use of a makeup composition comprising the pigment of invention, while these also beautify the skin and hidden the acneic imperfection underneath.
According to another aspect, the invention refers to cosmetic/dermatological compositions comprising the pigments described above.
The compositions according to the invention may also comprise any cosmetically acceptable ingredients, and can be associated with other components with auxiliary action in the treatment and prevention of acne or providing skin benefits.
Examples of said additional components are, for instance, other ingredients active against proliferation of Propionibacterium acnes, e. g. antibiotics such as erythromycin, clindamycin and tetracyclines; antimicrobials such as chlorexidine and benzoylperoxide, synthetic or natural substances described as possessing inhibitory activity against P. acnes such as 1-pentadecanol and derivatives thereof, cedrene, caryophyllene, and longifolene; retinoids other-than-tretinoin such as adapalene, tazarotene, etc.; NSAID antinflammatory agents such as ibuprofen, naproxen, sulfacetamide; steroidal antinflammatory agents (e. g. hydrocortisone); vitamins; skin healing agents; and skin conditioners.
Further examples of said additional components are the Aj-Av substances itself, in the sense that, one or more of Aj- Av can be present both in form of C-bonded and dispersed (unbonded) form, i.e. admixed into the composition by physical means, hi this way the composition according to the invention afford both immediate and sustained release of As.
The pigments of the invention can be employed alone or in combination with others other non-coated or differently coated pigment, as well as nacres and/or fillers in makeup and sun protection compositions in any amounts between 0.1 and 80 % by weight or more.
The cosmetic/dermatologic comprising the pigment of the invention includes, for example, makeup cosmetics such as powder foundation, liquid foundation, cream foundation, oily foundation, stick foundation, pressed powder, face powder; lipstick, rouge; eye shadow, pencil, and liner; mascara; fundamental cosmetics such as emollient cream, emollient lotion, milky lotion, massage lotion, cold cream, whitening cream, emulsion, lotion, aesthetic lotion, carmine lotion; cleansing cosmetic/dermatologic for makeup, cleansing jell, liquid wash, washing foam, washing cream, washing powder; and others including cream and emulsions for sun screening and sun tanning. Preferred cosme-dermatologic compositions are the foundations in different form, and the fundamental cosmetics as listed herein.
Finally, the scope of the composition comprising the pigments of invention and of the curative method of invention are:
1. sustain release of substances promoting skin exfoliation and/or to disinfect skin; 2. carry out bactericidal or bacteriostatic action on causative organism Propionibacteria acnes ("P. acnes");
3. prevent comedonal secondary infection with any other organisms like gram+ bacteria, gram- bacteria and pathogenic fungi;
4. promote the exfoliation of high proliferating layers that accompany the inflammatory nodules and lead to comedone formation;
6. restore the skin complexion by covering acne disorders or acne disfiguring sings;
7. provide a beautifying cosmetic makeup to give aesthetic comfort;
8. normalize sebum secretion to avoid follicular plugging;
9. avoid an immediate, high gradient of anti-acne substances to come into contact with skin and thus to provoke skin irritation;
10. finally, supply a synergistic combination of components in treatment of acneic skin.
Accordingly, the composition of invention may appropriately be compounded, e.g. with pigment dispersants, oils, surfactants, UV absorbents, preservatives, anti- oxidants, film forming agents, emollient agents, thickeners, dyes, and fragrance within a broad range with further advantages of the inventive purposes.
EXAMPLES
PIGMENT PREPARATION - MATERIALS AND METHODS The materials used in the preparation of the pigments are listed in Table I TABLE I
Type Compound Brand/Type Supplier; Origin
Ci Titanium dioxide TiO2 Tioxide RHD2™ Tioxide Europe; Follonica (IT)
Cj Zinc oxide ZnO Alfa Aesar J. M.; Karlsruhe (D)
Cj Alumina Al2O3 Sigma- Aldrich; Milan (IT)
CU Iron oxide black Fe3O4 Diploxide™ 88P Rockwood Specialties; Turin (IT)
Qi Iron oxide red Fe2O3 Diploxide™ 226P Rockwood Specialties; Turin (IT)
Qi Iron oxide yellow FeOOH Diploxide™ 51OP Rockwood Specialties; Turin (IT)
CiH Mica Mica M Merck; Darmstadt (D)
Qϋ Bismuth oxychloride BiOCl Biron Fines Merck; Darmstadt (D)
Aj Mono-ethyl fumarate Shanghai Huawan Chem. (China) Au N- Acetyl cysteine Zambon; Bresso (IT)
AU S-palmitoyl cysteine obtained according to Biochem. J., 1999 343 pag. 558.
Au Procysteine Sigma- Aldrich; Milan (IT)
AiU Salicylic acid ACEF; Fiorenzuola d'Arda (IT)
AiU Gentisic acid Baslini. Darfo (IT) Aiv Pyrithione ACEF; Fiorenzuola d'Arda (IT)
Av Octopirox Sigma- Aldrich; Milan (IT)
Ayi Tretinoin (retinoic acid) - Sigma- Aldrich; Milan (IT)
M ZnCl2.6H2O; CaCl2.2H2O - Sigma- Aldrich; Milan (IT)
M CuCl2.2H2O; A1C13.6H2O - Sigma-Aldrich; Milan (IT) Bj Ricinoleic acid DrJ. Pharmachem (Bombay; Ind)
Bi Undecylenic acid Sigma-Aldrich; Milan (IT)
Bj Azelaic acid Cognis; Dusseldorf (D)
Bi Palmitic acid Kortacid™ 1698 Akzo Nobel; Arese (IT)
Bi DiNa stearoyl glutamate Plantapon™ ACG 35 Cognis; Dusseldorf (D) Bj Nε-lauroyl-L-lysine Amihope™ LL Ajinomoto; Tokyo (JP)
Bu Stearoyl phosphoric acid Knapsack™ MDST Clariant; Frankfurt (D)
Example A - Wet method
Into a 1 -litre beaker fitted with a mechanical stirrer are suspended 200 g of zinc oxide in 500 ml of water, then 50 ml of ZnCl2 IM are added. A pH from 3 to 5 is attained and the slurry is kept under stirring at 60°C for 25 min. In another 200-ml beaker 8 g of azelaic acid and 4 g of pyrithione are dissolved in 100 ml of NaOH IN under stirring. The solution is slowly poured under stirring into 1-1 beaker containing the slurry and the system is stirred at 60°C for other 25 min.
The slurry is finally filtered, the filtrate is washed with warm deionized water until the soluble salts are removed, and the resulting cake is dried at 8O0C and grinded. Example B - Semi-dry method
10 kg of zinc oxide are carried into a vacuum blender, then a hot solution of 250 g of salycilic acind and 800 g of undecylenic acid in 4 litres of ethanol is sprayed onto the pigment surface. The blender temperature is set at 80°C and the powdered system is rolled and dried for 1 hour. After a 10 minute post-process blend and cooling, the powder is discharged from the blender. Examples C - AA
Pigments prepared according by Example A or B are listed in Table II.
Noteworthy, in the wet-methods the amount of the water-soluble multivalent cation salt and the caustic soda can be adjusted according to the amount of A (and B) used. Whenever A (and B) in the form of alkaline salts are soluble and/or dispersible at room temperature, then the coating is carried out without warming; whilst the temperature is brought to 75-80°C when at least one of A and/or B not dissolves in water but as melted form (e.g. sodium palmitate).
TABLE II - Pigment according to the invention
Ex. M •1a/b A B B%
S-palmitoyl-Cysteine + Retinoic ZnO Zn acid 8:2 4 '
D ZnO Zn L-cysteine 5 Palmitate 3
E ZnO Zn Procysteine + Pyrithione 2 : 1 3 Ricinoleate 3
F ZnO Zn N-acetyl-cysteine + Pyrithione 2 : 1 3 Ricinoleate 3
G ZnO Zn Mono-ethyl fumarate 2 Undecylenic acid 4
H TiO2 Ca N-acetyl-cysteine 3 Stearoyl glutamate 3
I TiO2 Zn Pyrithione + Salicylic acid 3:1 2 Ricinoleate 4
J TiO2 Ti Pyrithione 2 Undecylenate 4
K TiO2 Al Benzoic acid 2 Undecylenate 6
L TiO2 Al Salicylic acid 2 Azelate 4
M TiO2 Ca Octopirox 3 Azelate 3
N Al2O3 Al Salycilic acid 2 Undecylenate 3
O Al2O3 Al Benzoic acid 4 Stearoyl glutamate 4
P Al2O3 Al Gentisic acid + L-cysteine 2:1 3 Stearyl phosphate 3
Q FeOOH Al Octopirox 3 Ricinoleate 3
R FeOOH Al Octopirox 1 Azelate 5
S Fe3O4 Zn Retinoic acid 0,5 Ricinoleate 3,5
T Fe3O4 Al Retinoic acid 0,5 Azelate 15,5
U Fe2O3 Zn Procysteine 3 Ricinoleate 3
V Fe2O3 Cu Mono-ethyl fumarate 6 Palmitate 2
W BiOCl Ca Octopirox 3 Stearyl phosphate 3
Y BiOCl Ca Pyrithione 2 Azelate 6
Nε-Lauroyl-L-
Z Mica Al Retinoic acid 4
0,4 lysinate
Nε-Lauroyl-L-
AA Mica Al 4
Benzoic acid 4 lysinate
Noteworthy, the combination of two A or two M are expressed as w/w ratio; whilst the content of A, and the optional B, are expressed as % on weight on C.
APPLICATIVE EXAMPLES (COMPOSITIONS) Applicative Examples 1-3 - Foundations
A fatty blend is produced by mixing waxes and oils at 80°C with stirring until a homogeneous mixture is obtained. The pigments and fillers are added always at 80°C and with stirring until a homogeneous color is obtained. The remainder of the components are added and the temperature is maintained at 80°C for 2 hours with
stirring. The resulting foundations have the following compositions:
Appl. Ex.1 Appl. Ex.2 Appl. Ex.3
Macrocrystalline wax 4.Og 4.Og 4.Og
Carnauba wax 6.Og 6.Og 6.Og
Octyl palmitate 14 g 14 g 14 g
Hydrogenated polyisobutane 17.5 g 17.5 g 17.5 g
Trilaurin 7.Og 7.Og 7.Og
Propyl paraben 0.1 g 0.1 g 0.1 g
Curative Fe3O4 of Appl. Ex. T 0.7 g 1.0 g 0.5 g
Curative Fe2O3 of Appl. Ex. V 1.9 g 1.7 g 2.1g
Curative FeOOH of Appl. Ex. Q 4.9 g 4.4 g 4.7 g
Curative TiO2 of Appl. Ex. K 16.6 g 9.Og -
Curative TiO2 of Appl. Ex. L - 8.Og 16.5 g
Curative ZnO of Appl. Ex. E 3.Og - 2.Og
Curative ZnO of Appl. Ex. F - 3.0g 1.3 g
Curative Mica of Appl. Ex. Z 15.Og 8.Og -
Curative Mica of Appl. Ex. AA 15.Og 7.Og 15.Og
Nylon (untreated) 8.Og 8,0g 8.0g
Benzophenone-3 0.5 g 0.5 g 0.5 g
Octyl methoxycinnamate 0.5 g 0.5 g 0.5 g
Dimethicone, 0.3 g 0.3 g 0.3 g
Applicative Example 4 - Beautifying dav cream
The emulsion contains: Glycerin 87% 3.0g
Decyl Glucoside 1.0 g
Xanthan Gum 0.3 g
D-Panthenol in Propylene Glycol 2.0 g
ZnO pigment of the Applicative Example G 5.0g Zinc undecylenate 4.0 g
Diethylamino Hydroxybenzoyl Hexyl Benzoate 2.0 g
Cycloniethicone 2.O g
Ceteareth-6, Stearyl Alcohol 5.5 g
Ceteareth-25 1.5 g
Bees Wax 0.5 g Caprylic/Capric Triglyceride 10.0 g
Tocopheryl Acetate 1.0 g
Preservatives and perfume q.s. Demineralized water q.b. to 100 g
METHOD OF USE
Efficacy and safety assessment
Ten acne-prone female subjects or undergoing acneic disorders are rated as follows: grade 0 = no comedones or papules but an history of recurring acne; grade I = a few to moderate comedones + a few papules; grade II = a few to moderate papules + a few pustules; grade III = a few to moderate pustules + nodule/cyst and scarring.
The subjects are given the Applicative Examples 1 or 2 or 3 according to their skin hues, to be applied on regular daily base as decorative foundation. The volunteers are assessed for the baseline and at the end of week 1, 2, 4, and 6. The assessment is scored according to the following scale: Irritation: 1. - = no irritation; 2. + = minimal; 3. ++ = moderate; 4. +++ = severe irritation. Efficacy score: 0. = unchanged; 1 = poor improvement; 2 = fair; 3 = high; 4 = very high improvement. Subject are asked to judge the following parameters: 1) = irritation (none, some or troublesome); 2) = dryness of skin (none, some or troublesome); 3) improvement in acne (none, satisfactory or very satisfactory); and 4) willingness to continue the product (yes or no).
Efficacy assessment at the end of 6th week showed that 8/10 had good to very good effect of treatment. At the end of 2nd week of treatment 4/10 showed good to very good improvement followed by 4/10 of subjects showing fair response. The profile of side effects revealed that 6/10 of subjects did not have any irritation, 3/10 had minimal irritation whereas 1 subject had moderate irritation.
Improvement of acne reported by the subjects, data showed that 7/10 subjects have
satisfactory improvement after 6 weeks, 2/10 reported very satisfactory improvement and only 1 has an unsatisfactory response. Assessment of irritation showed that 5/10 of subjects reported no irritation, 4/10 had some irritation, whereas only one subjects reported troublesome irritation. Dryness of skin reported dryness in 4/10 of subjects, only 1 reported troublesome dryness; low-to-no dryness is reported by 5/10 subjects.
Claims
CLAIMS 1. Pigment having the following structure (I):
- Ci : white inorganic pigments;
- Qi : coloring inorganic pigments;
- Qϋ : extender pigments;
- Cjv : composite pigments; - Cv : organic pigments;
A denotes an anion of the anion of a substance capable to promote skin exfoliation and/or to disinfect skin selected from:
- Ai : fumarates and mono-ester thereof;
- AJ1 : cysteine and derivatives thereof; - Aiϋ : benzoates and salicylates;
- Ajv : 2-pyridmethiol 1 -oxides;
- Av : l-hydroxy-2-pyridones;
- AVi : tretinoin and analogs;
B denotes a hydrophobic anionic surfactant selected from: - Bj : carboxylic-ended surfactants;
- Bii : phosphoric-ended surfactants;
- Biϋ : sulfonic-ended surfactants;
Ma and Mb denote, each independently, a multivalent cation selected from the group consisting of: Zn2+, Cu2+, Ca2+, Ti4+, Si4+, Al3+, Sn4+, Mg2+, Sr2+, Ti4+, Zr4+, Ce4+, Fe2+/3+, Cr6+ , Mn2+, and combination thereof; the ratio b/a are comprised from 0 to about 10 w/w; and A is in the range of 0.1% to 20% w/w on C; B is in the range of 0% to 8% w/w on C.
2. Pigment according to claim 1 wherein Ma is Zn2+, Al3+ or Ca2+.
3. Pigment according to claim 1 wherein Mb is Zn2+, Al3+ or Ca2+.
4. Pigment according to claim 1 wherein A1 is fumaric acid or a mono-C1-5-alkyl- or -Aϋj-ester thereof.
5. Pigment according to claim 1 wherein AH is L-cysteine, or a N- and/or S-acyl- cysteine; or a cysteine prodrug selected from the group consisting of: L-cysteine, N-acetyl-cysteine, S-carboxymethyl-cysteine, S-palmitoyl-cysteine, and procysteine.
6. Pigment according to claim 1 wherein Aiϋ is a benzoic acid, a 1 -hydroxy-benzoic acid, or a 1,5-dihydroxy-benzoic acid, or a derivative thereof selected from the group consisting of: benzoic acid, salicylic acid, acetyl salicylic acid, benzyl salicylate, and gentisic acid.
7. Pigment according to claim 1 wherein AjV is a substituted or unsubstiruted 2- pyridinethiol 1 -oxide, preferably pyrithione.
8. Pigment according to claim 1 wherein Av is a 4,6-dialkyl-l-hydroxy-2(7H}- pyridinone, preferably octopirox.
9. Pigment according to claim 1 wherein Avi is retinoic acid or an analog thereof selected from the group consisting of: tretinoin alitretinoin, isotretinoin, adapalene, bexarotene, fenretinide, acitretin; or a free-carboxylic or free-phenolic containing arotinoid.
10. Pigment according to claim 1 wherein the ratio b/a = 0.
11. Pigment according to claim 1 wherein the ratio b/a can vary from 0.1 to 10 w/w.
12. Pigment according to claim 1 wherein Bi is selected from the group consisting of: carboxylate of formula 0OOC-R; dicarboxylate of formula (")OOC-R"-COO("); α-hydroxycarboxylate of formula 0OOC-CHR' -O-CO-R; alkylsuccinamate of formula 9OOC-CH2CH2-O-CO-R ; N-alkanoyl-sarcosinate or -glycinate of formula °OOC-CH2-NR'-CO-R; N-acylglutamate or N-acylaspartate of formula 0OOC-CH2(CH2)C1CH(NH-CO-R)-COO0 ; and Nε-acyl-lysinate of formula (' )OOC-CH(NH2)-(CH2)4-NH-CO-R.
13. Pigment according to claim 12 wherein Bj is undecylenic acid or riconoleic acid.
14. Pigment according to claim 12 wherein the dicarboxylate of formula 0OOC-R"-
COO^ is selected from the group consisting of: adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and dodecandioic acid.
15. Pigment according to claim 1 wherein BH is an alkyl- or diaUkyl-phosphate of formula: (")OaP(O)-(OR)b; wherein a=l or 2; and b=3-a.
16. Pigment according to claim 1 wherein BJU is selected from the group consisting of: alkyl sulfonate of formula (2'}O3S-R ; alkylsulfate of formula 00O3S-O-R ; alkyl ester sulfonate of formula: ^O3S-CHR-COOR'; alkyl amide sulfate of formula ^O3SO-NHR' -CO-R; alkyl-isethionate of formula: ^O3S-CH2CH2- CO-R; N-acyl-N-alkyltaurate of formula ^O3S-CH2CH2-NR' -CO-R; C9-C20- alkylbenzen-sulfonate; alkylsulfosuccinate of formula (2")O3S-CH(COOR')-CH2-
R sulfosuccinate monoesters or diesters; alkylglycosides sulphate.
17. Pigment according to one of claim 12, 1 5 or 16 wherein the -OR or -0-COR radicals contained in Bj, BU and Bu; are saturated or unsaturated, linear or branched, C8-C20-alkyl or -acyl groups; said R optionally comprising a polyalkoxy chain of formula -(0CH2CHR')z-0- with z comprised between 1 and
100, preferably between 1 and 10.
18. Pigment according to one of claim 12, 1 5 or 16 wherein each R' is H or C1-C3 alkyl, preferably methyl.
19. Cosmetic/dermatologic composition comprising a pigment according to one ore more of claims 1-18 in an amount between 3% to 80% by weight.
20. Composition according to claim 30 in the form of foundation, pressed pigment, face pigment, mascara, anhydrous or hydrated emulsion, or paste.
21. Composition according to claim 30 comprising other components with auxiliary action in the treatment and prevention of acne or provide skin benefits.
22. Composition according to claim 30 which contains at least one additive having neither cosmetic activity nor dermopharmaceutical activity selected from the group consisting of a gelling agent, a polymer, a preservative, a colorant, an opacifier and a perfume.
23. Method to promote skin exfoliation and/or to disinfect skin and thus to treat acneic skin, while also providing an attractive coloration to the skin by the regular use of a composition according to one or more claims 20 to 22.
24. Method according to claim 23 wherein said composition and their use provide:
1. sustain release of substances promoting skin exfoliation and/or to disinfect skin;
2. carry out the bactericidal or bacteriostatic action on causative organism;
3. prevent comedonal secondary infection with any other organisms like gram+ bacteria, gram- bacteria and pathogenic fungi;
4. promote the exfoliation of high proliferating layers that accompany the inflammatory nodules and lead to comedone formation;
6. restore skin complexion by covering acne disorders or acne disfiguring sings;
7. provide a beautifying cosmetic makeup to give aesthetic comfort; 8. normalize sebum secretion to avoid follicular plugging;
9. avoid an immediate, high gradient of anti-acne substances to come into contact with skin and thus to provoke skin irritation;
10. finally, the different components synergistically helps to treat acneic skin.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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IBPCT/IB2006/000090 | 2006-01-20 | ||
PCT/IB2006/000090 WO2007083174A1 (en) | 2006-01-20 | 2006-01-20 | Curative pigments and make-up comprising thereof |
Publications (2)
Publication Number | Publication Date |
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WO2007083184A2 true WO2007083184A2 (en) | 2007-07-26 |
WO2007083184A3 WO2007083184A3 (en) | 2008-04-10 |
Family
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Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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PCT/IB2006/000090 WO2007083174A1 (en) | 2006-01-20 | 2006-01-20 | Curative pigments and make-up comprising thereof |
PCT/IB2006/003579 WO2007083184A2 (en) | 2006-01-20 | 2006-12-12 | Cosmetic dermatology in acneic and comedogenic skin |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/IB2006/000090 WO2007083174A1 (en) | 2006-01-20 | 2006-01-20 | Curative pigments and make-up comprising thereof |
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Families Citing this family (3)
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EP2293761B1 (en) * | 2008-05-12 | 2017-02-01 | Tagra Biotechnologies Ltd | Compositions for topical application comprising microencapsulated colorants |
DE102010021671A1 (en) * | 2010-05-27 | 2011-12-01 | Intendis Gmbh | Azelaic acid-containing formulation with added pigment |
ITRM20110400A1 (en) | 2011-07-27 | 2013-01-28 | Uni Politecnica Delle Marche | NEW COMPOSITIONS FOR SOLAR PROTECTION. |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1467409A1 (en) * | 1964-11-16 | 1968-12-12 | Ayers Joseph Williams | Pigment particles coated with organo-aluminum compounds |
US3951680A (en) * | 1973-05-02 | 1976-04-20 | E. I. Du Pont De Nemours And Company | Filled polyolefin compositions |
FR2537987A1 (en) * | 1982-12-18 | 1984-06-22 | Pilot Ink Co Ltd | INK FOR MARKERS CONTAINING SURFACE-TREATED TITANIUM BIOXIDE |
WO2001055262A1 (en) * | 2000-01-28 | 2001-08-02 | Carlo Ghisalberti | New pigments and compositions containing them |
WO2005094156A2 (en) * | 2004-03-31 | 2005-10-13 | Basf Aktiengesellschaft | Polyasparaginic acid surface-modified metal oxides methods for production and use thereof in cosmetic preparations |
-
2006
- 2006-01-20 WO PCT/IB2006/000090 patent/WO2007083174A1/en active Application Filing
- 2006-12-12 WO PCT/IB2006/003579 patent/WO2007083184A2/en active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1467409A1 (en) * | 1964-11-16 | 1968-12-12 | Ayers Joseph Williams | Pigment particles coated with organo-aluminum compounds |
US3951680A (en) * | 1973-05-02 | 1976-04-20 | E. I. Du Pont De Nemours And Company | Filled polyolefin compositions |
FR2537987A1 (en) * | 1982-12-18 | 1984-06-22 | Pilot Ink Co Ltd | INK FOR MARKERS CONTAINING SURFACE-TREATED TITANIUM BIOXIDE |
WO2001055262A1 (en) * | 2000-01-28 | 2001-08-02 | Carlo Ghisalberti | New pigments and compositions containing them |
WO2005094156A2 (en) * | 2004-03-31 | 2005-10-13 | Basf Aktiengesellschaft | Polyasparaginic acid surface-modified metal oxides methods for production and use thereof in cosmetic preparations |
Non-Patent Citations (1)
Title |
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J. FALBE, M. REGITZ (ED.): "Römpp, Chemie Lexikon Vol. T-Z" 1995, GEORG THIEME VERLAG , STUTTGART NEW YORK , XP002402953 page 4821; compound UNDECENSÄURE * |
Also Published As
Publication number | Publication date |
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WO2007083174A1 (en) | 2007-07-26 |
WO2007083184A3 (en) | 2008-04-10 |
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