EP1392785A1 - System zur freisetzung von aktivstoffen und wirkstoffen - Google Patents
System zur freisetzung von aktivstoffen und wirkstoffenInfo
- Publication number
- EP1392785A1 EP1392785A1 EP02743098A EP02743098A EP1392785A1 EP 1392785 A1 EP1392785 A1 EP 1392785A1 EP 02743098 A EP02743098 A EP 02743098A EP 02743098 A EP02743098 A EP 02743098A EP 1392785 A1 EP1392785 A1 EP 1392785A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- active substance
- sol
- gel
- active
- coatings
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000013543 active substance Substances 0.000 title claims abstract description 177
- 238000000034 method Methods 0.000 claims abstract description 62
- 238000000576 coating method Methods 0.000 claims abstract description 61
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 238000013270 controlled release Methods 0.000 claims abstract description 11
- 230000001681 protective effect Effects 0.000 claims abstract description 4
- 238000003860 storage Methods 0.000 claims abstract description 4
- 239000011159 matrix material Substances 0.000 claims description 43
- 230000008569 process Effects 0.000 claims description 35
- 239000011521 glass Substances 0.000 claims description 24
- 229920000858 Cyclodextrin Polymers 0.000 claims description 21
- 239000002243 precursor Substances 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 17
- 239000011248 coating agent Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 229940097362 cyclodextrins Drugs 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000011148 porous material Substances 0.000 claims description 13
- 239000003921 oil Substances 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 10
- 239000003205 fragrance Substances 0.000 claims description 10
- 150000004645 aluminates Chemical class 0.000 claims description 9
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 9
- 150000004760 silicates Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 8
- 230000006870 function Effects 0.000 claims description 8
- -1 aluminum compound Chemical class 0.000 claims description 7
- 239000012876 carrier material Substances 0.000 claims description 7
- 239000000975 dye Substances 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 239000010703 silicon Substances 0.000 claims description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 230000000844 anti-bacterial effect Effects 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical group CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 claims description 5
- 239000011782 vitamin Substances 0.000 claims description 5
- 229940088594 vitamin Drugs 0.000 claims description 5
- 229930003231 vitamin Natural products 0.000 claims description 5
- 235000013343 vitamin Nutrition 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 239000007844 bleaching agent Substances 0.000 claims description 4
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical class COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 230000004224 protection Effects 0.000 claims description 4
- 235000012239 silicon dioxide Nutrition 0.000 claims description 4
- 239000002689 soil Substances 0.000 claims description 4
- 102000004190 Enzymes Human genes 0.000 claims description 3
- 108090000790 Enzymes Proteins 0.000 claims description 3
- 229940088598 enzyme Drugs 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 238000011068 loading method Methods 0.000 claims description 3
- 239000002304 perfume Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 239000000341 volatile oil Substances 0.000 claims description 3
- 102000013142 Amylases Human genes 0.000 claims description 2
- 108010065511 Amylases Proteins 0.000 claims description 2
- 102000005575 Cellulases Human genes 0.000 claims description 2
- 108010084185 Cellulases Proteins 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 102000004882 Lipase Human genes 0.000 claims description 2
- 108090001060 Lipase Proteins 0.000 claims description 2
- 239000004367 Lipase Substances 0.000 claims description 2
- 102000035195 Peptidases Human genes 0.000 claims description 2
- 108091005804 Peptidases Proteins 0.000 claims description 2
- 239000004365 Protease Substances 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 235000019418 amylase Nutrition 0.000 claims description 2
- 229940025131 amylases Drugs 0.000 claims description 2
- 230000000845 anti-microbial effect Effects 0.000 claims description 2
- 230000000840 anti-viral effect Effects 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000000035 biogenic effect Effects 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 239000000645 desinfectant Substances 0.000 claims description 2
- 238000002845 discoloration Methods 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 230000002255 enzymatic effect Effects 0.000 claims description 2
- 239000007850 fluorescent dye Substances 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 claims description 2
- 239000008240 homogeneous mixture Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 2
- 235000019421 lipase Nutrition 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 229910052605 nesosilicate Inorganic materials 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 239000006174 pH buffer Substances 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 239000005080 phosphorescent agent Substances 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 230000009993 protective function Effects 0.000 claims description 2
- 230000002940 repellent Effects 0.000 claims description 2
- 239000005871 repellent Substances 0.000 claims description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims description 2
- 229920002545 silicone oil Polymers 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 239000003002 pH adjusting agent Substances 0.000 claims 1
- 238000003980 solgel method Methods 0.000 abstract description 5
- 239000007858 starting material Substances 0.000 abstract description 2
- 239000011241 protective layer Substances 0.000 abstract 2
- 239000012703 sol-gel precursor Substances 0.000 abstract 1
- 239000000499 gel Substances 0.000 description 57
- 235000019198 oils Nutrition 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 2
- 239000001116 FEMA 4028 Substances 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical class OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 2
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 2
- 229960004853 betadex Drugs 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 210000000567 greater sac Anatomy 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002452 interceptive effect Effects 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
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000002899 organoaluminium compounds Chemical class 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/042—Gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/24—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients to enhance the sticking of the active ingredients
-
- 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
- A61K8/0283—Matrix particles
-
- 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
- A61K8/73—Polysaccharides
- A61K8/738—Cyclodextrins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7015—Drug-containing film-forming compositions, e.g. spray-on
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C1/00—Ingredients generally applicable to manufacture of glasses, glazes, or vitreous enamels
- C03C1/006—Ingredients generally applicable to manufacture of glasses, glazes, or vitreous enamels to produce glass through wet route
- C03C1/008—Ingredients generally applicable to manufacture of glasses, glazes, or vitreous enamels to produce glass through wet route for the production of films or coatings
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/624—Sol-gel processing
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/0082—Special methods for preparing compositions containing mixtures of detergents one or more of the detergent ingredients being in a liquefied state, e.g. slurry, paste or melt, and the process resulting in solid detergent particles such as granules, powders or beads
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/38—Products with no well-defined composition, e.g. natural products
- C11D3/386—Preparations containing enzymes, e.g. protease or amylase
- C11D3/38672—Granulated or coated enzymes
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
- C11D3/502—Protected perfumes
- C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
-
- 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
- A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
-
- 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
- A61K2800/65—Characterized by the composition of the particulate/core
- A61K2800/651—The particulate/core comprising inorganic material
-
- 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
- A61K2800/65—Characterized by the composition of the particulate/core
- A61K2800/652—The particulate/core comprising organic material
Definitions
- the present invention relates to a system for releasing active substances or active substances, in particular from surfaces.
- the present invention relates to a mass containing active substance and / or active substance, in particular for the production of films, layers and / or coatings on surfaces, and a process for their production and their use.
- active substances or active substances such as fragrances, essential oils, perfume oils and care oils, dyes or pharmaceutically active substances, which are used in cosmetic and / or pharmaceutical products or in detergents and cleaning agents, often lose during storage or directly during use their activity.
- Sensitive substances are often enclosed in capsules of various sizes, adsorbed on suitable carrier materials or chemically modified. The release can then be activated with the aid of a suitable mechanism, for example mechanically by shearing, or can take place diffusively directly from the matrix material.
- Systems are therefore sought that are suitable as encapsulation, transport or presentation vehicles - often synonymously also referred to as “delivery systems” or “carrier systems”.
- the object of the present invention is therefore to provide a new carrier system for active substances and / or active substances, which in particular enables a controlled release of these substances.
- Another object of the present invention is to provide a system with a depot and release function for active substances and active substances, in particular on surfaces.
- the object of the present invention is in particular the development of a coating for the depot maintenance and / or controlled release of active substances or active substances, such as, for example, colorants and fragrances, care oils, vitamins, enzymes, antibacterially active substances or other active substances.
- active substances or active substances such as, for example, colorants and fragrances, care oils, vitamins, enzymes, antibacterially active substances or other active substances.
- the present invention thus relates to a process for the preparation of a mass containing active substance and / or active substance, which is particularly suitable for the production of films, coatings, layers and / or coatings, a sol / gel process being carried out in the presence of at least one Carried active substance and / or active substance carries out.
- Sol / gel processes per se are readily familiar to the person skilled in the art (see, for example, Römpp-Lexikon Chemie, 9th edition, volume 5, page 4140, keyword “sol-gel process” and literature cited therein; CJ Brinker, GW Scheerer, "Sol-Gel-Science: The physics and chemistry of sol-gel processing", Academic Press, San Diego, 1998).
- the term "sol-gel process” or “sol-gel process” means a process in which glasses or ceramic compositions are finally obtained from initially soluble compounds via the intermediate stage of a gel.
- sol / gel processes have not yet been used to generate depot or release systems for active substances. It is thanks to the applicant that it has found that sol / gel processes are suitable for generating systems of the type mentioned above.
- a sol / gel process is therefore carried out in the presence of a suitable sol / gel precursor (sol / gel precursor) and a carrier molecule loaded with at least one active substance and / or active substance, ie in other words the gel formation is started achieved by a suitable sol / gel precursor in the presence of a carrier molecule loaded with at least one active substance and / or active substance.
- the carrier molecule loaded with at least one active substance and / or active substance is embedded in a preferably porous sol / gel matrix (gel matrix) formed in the sol / gel process.
- the sol / gel precursor must therefore lead to gel formation in a sol / gel process, in particular under hydrolysis conditions (for example acid hydrolysis, for example with hydrochloric acid) with subsequent polycondensation reaction.
- Sol / gel precursors suitable according to the invention i. H. Starting compounds capable of gel formation are known per se to the person skilled in the art.
- Sol / gel precursors which can be used according to the invention are, for example, compounds of silicon, boron, aluminum, titanium, zirconium, vanadium etc. which are capable of gel formation.
- suitable silicon / boron and / or are preferred as sol / gel precursors
- Aluminum compounds, in particular organosilicon, organoboron and / or organoaluminium compounds, are used.
- Sol / gel precursors suitable according to the invention are in particular selected from the group of di-, tri- and / or tetrafunctional silicic acid, boric acid and aluminum esters, in particular alkoxysilanes (alkyl orthosilicates), and their precursors.
- sol / gel precursors suitable according to the invention are alkoxysilanes of the general formula
- X represents hydrogen or a radical -OR 3 ,
- R 1 , R 2 , R 3 and R 4 each independently of the other, denote an organic radical, in particular a linear or branched alkyl radical, preferably (-C-d 2 ) alkyl.
- Compounds which are particularly preferred according to the invention are the silicic acid esters tetramethyl orthosilicate (TMOS) and tetraethyl orthosilicate (TEOS).
- sol / gel precursors suitable according to the invention are described, for example, in German patent application 100 21 165.9 of Henkel KGaA dated April 29, 2000 with the designation "system for the release of active substances", the disclosure of which is hereby fully incorporated by reference.
- organosilanes such as.
- the sol / gel process is carried out with the aforementioned sol / gel precursors in a manner known per se to the person skilled in the art, namely generally by hydrolysis of these compounds, in particular in the presence of acids, bases or other catalysts such as, for. B. fluorides, with subsequent polycondensation reaction. Acid hydrolysis is preferred according to the invention.
- the sol / gel process i. H. the gelling (in particular hydrolysis with subsequent polycondensation) is then generally followed by removal of the solvent or dispersion medium which may be present. Generally this is done by heat treatment.
- the heat treatment which can optionally be carried out under reduced pressure or vacuum, can in particular be carried out at temperatures from approximately 20 ° C. to approximately 100 ° C. or more.
- the heat treatment is carried out in particular for a period of about 1 hour to about 24 hours or more.
- the sol / gel process and heat treatment can, for example, also merge continuously.
- the heat treatment not only removes any solvent that may be present, but also the preferably porous gel matrix (sol / gel matrix) - by further chemical conversion - into a preferably porous glass matrix (sol / gel glass matrix), in which the Carrier molecules loaded with active substance and / or active substance are embedded.
- a matrix based on polysilicic acids, silicates, borates and / or aluminates is formed.
- the active substance- and / or active substance-containing mass produced according to the invention and obtainable by the sol / gel process can be applied in films, coatings, layers and / or coatings to the surface of a suitable carrier material, so that coated surfaces are then formed after the heat treatment , as explained below.
- Surface carrier materials suitable according to the invention, to which the coating composition produced according to the invention can be applied are, for example, glasses and ceramics of all kinds; inorganic oxides such as aluminum oxide, silicon dioxide, magnesium oxide, boron oxide, titanium oxide, etc .; silica gels; Cellulose products of all kinds; Plastic products of all kinds; Fabrics, fabrics, fleeces, knitted fabrics and felts of all kinds; Metals and metal alloys of all kinds; and other, preferably inert carriers and carrier materials as well as macro- and mesoporous carriers. Spherical carrier particles of the aforementioned materials are also suitable as carriers.
- the present invention thus relates to a process for producing a mass containing active substance and / or active substance, in particular for producing films, layers and / or coatings, which comprises the following process steps:
- step (b) preparation of a homogeneous mixture of the carrier molecule loaded in step (a) with a suitable sol / gel precursor, optionally in the presence of a suitable solvent or dispersant; (c) carrying out a sol / gel process in the mixture prepared in step (b), so that a preferably porous sol / gel matrix is formed in which the carrier molecules loaded with active substance and / or active substance are embedded;
- step (d) optionally heat treatment of the sol / gel matrix produced in step (c), so that any solvent or dispersion medium present is removed and a preferably porous sol / gel glass matrix, preferably based on polysilicic acids, silicates, borates and / or Aluminates is formed, in which the active substance and / or active substance-loaded carrier molecules are embedded.
- the mixture produced in step (b) and / or the sol / gel matrix produced in step (c) can be processed or applied to form films, coatings, layers and / or coatings.
- the mixture produced in step (b) and / or the sol / gel matrix produced in step (c) can be applied to a preferably inert carrier surface, preferably as a film, coating, layer and / or coating;
- a preferably inert carrier surface preferably as a film, coating, layer and / or coating
- Layer thicknesses of 100 nm to 10 mm, in particular 1,000 nm to 2 mm, are preferred.
- the carrier surface coated with the carrier molecules loaded with active substance and / or active substance can be subjected to a heat treatment, so that any solvent or dispersion medium present is removed and one with a preferably porous sol / gel-glass matrix, preferably based on silicates, polysilicic acids, borates and / or aluminates, results in a coated support surface, the sol / gel-glass matrix containing the active substance- and / or active substance-loaded carrier molecules in stored form, preferably in a homogeneous distribution ; in other words, the heat treatment causes the gel matrix initially produced by the sol / gel process - also referred to synonymously in the present application as "sol / gel matrix" - into a glass matrix - synonymously also in the present application as "sol / gel glass matrix” designated - converted.
- the sol process is carried out in the presence of a carrier molecule loaded with at least one active substance and / or active substance.
- the carrier molecule is a molecule or a compound with molecular cavities, cavities, pores, channels, pockets or the like, which can accommodate the respective active substance and / or active substance molecules.
- the carrier molecule or the carrier compound must have sufficiently large molecular cavities, cavities, pores, channels, pockets or the like in order to take up the respective active substance and / or active substance molecules, ie to store, include, complex, etc.
- Cavities with diameters of about 200 to about 1,500 pm, in particular about 300 to about 1,400 pm, preferably about 400 to about 1,350 pm, are required.
- the molecular cavities, cavities, pores, channels, pockets or the like of the carrier molecules contain polar groups, for example are hydrophilic or hydrophobic, depending on the type and nature of the active substance and / or active substance molecule to be included.
- the carrier molecule is preferably an organic carrier molecule.
- carrier molecules suitable according to the invention are all molecules, in particular organic in nature, with molecular cavities, cavities, pores, channels, pockets or the like which are sufficiently large to accommodate the respective active substance and / or active substance molecules, i.e. H. store, enclose, complex, etc.
- the carrier molecule can be selected from the group of cyclodextrins (cycloamyloses, cycloglucans) and calixarenes, optionally in modified and / or activated form, as well as their derivatives and mixtures. If cyclodextrins according to the invention as carrier molecules used, these can be selected from the group of ⁇ -, ⁇ - and ⁇ -cyclodextrins, optionally in modified or activated form, and their derivatives. Examples of functionalized or modified cyclodextrins include, for example, alkyl and / or hydroxyalkyl and / or amino group-substituted cyclodextrins.
- the concentration ratio of active substance or active substance to carrier molecule can vary within wide limits and can reach, for example, up to 1: 1 (molar), ie. H. one active substance or active substance molecule per carrier molecule.
- the concentration of the carrier molecule loaded with active substance and / or active substance (eg cyclodextrin-active substance complex) in the starting solution or dispersion for the sol / gel process can likewise be in wide ranges vary and, for example, 0.1 to 99 wt .-%, in particular 5 to 25 wt .-%, based on the starting solution or dispersion
- the concentration of sol / gel precursor in the starting solution or dispersion can likewise vary within wide ranges and for example 20 to 80% by weight, in particular 30 to 60% by weight, be.
- the sol / gel process itself can be carried out in wide temperature ranges, in particular at 0 to 100 ° C., preferably 20 to 80 ° C., particularly preferably 40 to 60 ° C.
- the reaction time can be about 1 hour to about 2 days, preferably 2 hours. It is preferably carried out at low or acidic pH values, in particular at pH values below 7, in particular from 0 to 3, preferably 1, 7 to 2.
- a typical representation of organic-inorganic hybrid layers according to the invention by means of the sol / gel process looks as follows:
- the representation of suitable coating solutions or dispersions is carried out by mixing a suitable sol / gel precursor, such as, for. B. a tetraalkoxysilane or tetraalkyl orthosilicate of the formula Si (OR) 4 such as TMOS or TEOS, with a suitable hydrolysis agent (e.g. hydrochloric acid HCI) and with the complexed or embedded active substance and / or active substance in an organic carrier molecule.
- a suitable sol / gel precursor such as, for. B. a tetraalkoxysilane or tetraalkyl orthosilicate of the formula Si (OR) 4 such as TMOS or TEOS
- a suitable hydrolysis agent e.g. hydrochloric acid HCI
- complex carrier molecules substances with molecular cavities, such as.
- cyclodextrins or calixarenes
- the complexing molecule suitable for each active ingredient must be chosen based on the size of the molecular cavity.
- the coating solution is then, for example, on a solid support, e.g. B. a glass plate, applied. After heat treatment at, for example, approximately 60 ° C. for 24 hours and, if appropriate, under the action of a vacuum, a solid film containing the active ingredient is produced.
- the incorporation of molecular complexes from carrier molecules such as. As cyclodextrins, and coordinated active substance and / or active substance molecules sufficient to achieve a controlled release of the active substances from the coatings.
- the release is then only determined by the complexation constant for the active ingredient and / or active ingredient in the carrier molecule (e.g. cyclodextrin or calixarene) and the rate of diffusion of the active ingredient through the coating material (e.g. silicate).
- the release therefore requires either a porosity of the material and / or a certain solubility of the active substance in the material so that access to the surface of the coating and thus release can take place. This is usually the case.
- any active substances and / or active substances can be used as active substances and / or active substances with which the carrier molecules are loaded.
- those active substances and / or active substances are preferred which are essentially inert under the reaction conditions of the sol / gel process or which are essentially not converted.
- the active substance or active substance is at least partially soluble in the gel and / or glass matrix.
- the active substance and / or active substance can be selected from the group of fragrances; Oils such as essential oils, perfume oils, care oils, fragrance oils and silicone oils; antibacterial, antiviral or fungicidal active substances; disinfectant and antimicrobial substances; deodorants; Anti-oxidants; pharmaceutically active substances; biologically active substances and biogenic active substances; Vitamins and vitamin complexes; Enzymes and enzymatic systems such as amylases, cellulases, lipases and proteases; cosmetically active substances such as ingredients for cosmetics and personal care products; substances active in washing and cleaning, such as all kinds of surfactants, inorganic and organic acids active in washing and / or cleaning, Soil repellent and soil release agents, oxidants and bleaching agents such as in particular hypochlorites and peroxides, bleach activators, builders and cobuilders, anti-redeposition additives, graying and discoloration inhibitors, active substances for color protection, substances and additives for laundry care, optical brighteners, pH inhibitors, foam inhibitors Adjust
- the process according to the invention leads to the production of masses containing active substance and / or active substance, which are particularly suitable for the production of films, coatings, layers and / or coatings on support surfaces of all kinds.
- the method according to the invention therefore likewise represents a method for producing carrier surfaces with a protective function and / or depot retention of active substances and / or active substances and thus also a method for the protection and / or depot retention of active substances and / or active substances, in particular on carrier surfaces Carrier surfaces coated in this way have a controlled release function for active substances and / or active substances.
- the present invention also relates to the active substance- and / or active substance-containing compositions, in particular for the production of films, coatings, layers and / or coatings which can be obtained by the process according to the invention, and the films, coatings, layers and / or coatings produced therefrom ,
- films, coatings, layers and / or coatings which comprise a preferably porous sol / gel glass matrix, in particular based on polysilicic acids, silicates, borates and / or aluminates, with - preferably being homogeneously distributed over the matrix - Carrier molecules are embedded, in the molecular cavities, cavities, pores, channels or the like active substance and / or active substance molecules are embedded and / or complexed.
- thicknesses are used for the films, coatings, layers, coatings or the like of 100 nm to 10 mm, in particular 1,000 nm to 2 mm, preferred.
- the present invention also relates to surfaces, in particular surfaces of inert carrier materials, to which films, coatings, layers, coatings or the like of the aforementioned type are applied. As described above, these are in particular surfaces with a protective and / or depot function for active substances and / or active substances or with a controlled release function for active substances and / or active substances.
- the method according to the invention offers a number of advantages. To name just a few, the following are mentioned by way of example:
- the method according to the invention enables the production of coatings with a depot function for the controlled release of active substances or active substances.
- these spontaneously form self-assembled aggregates in the surface coating, in particular silicate coating, which control the release properties.
- the release kinetics can be controlled via the size and geometry of the self-organized aggregation structures.
- Another advantage of the present invention is the fact that the coatings, layers, coatings, films and the like can be produced directly from solution.
- inorganic-organic hybrid depot systems are formed which are suitable for the particularly controlled release of active substances or active substances from surfaces, in particular in the form of coatings, layers, coatings, Films etc., so that they can be used in numerous fields of application.
- Other advantages of the present invention will be readily apparent to those skilled in the art upon reading the description.
- the present invention is illustrated using the following exemplary embodiments, which, however, are in no way intended to limit the invention.
- Coatings were made on glass substrates by pouring a solution from the recipes given below. The coatings were allowed to react in a drying cabinet at 60 ° C for 24 hours. Thereafter, solid coatings were obtained, from which the active ingredient was released with a great delay.
- a solution of 10 g of hydroxypropyl-substituted ⁇ -cyclodextrin loaded with orange oil is mixed with 10 g of water and 27.5 g of TEOS and brought to a pH of 1.7 with HCl.
- a solution of 10 g of phenol-loaded methyl-substituted ⁇ -cyclodextrin is mixed with 10 g of water and 27.5 g of TEOS and brought to a pH of 1.7 with HCl.
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10126966 | 2001-06-01 | ||
| DE10126966A DE10126966A1 (de) | 2001-06-01 | 2001-06-01 | System zur Freisetzung von Aktivstoffen und Wirkstoffen |
| PCT/EP2002/005752 WO2002098998A1 (de) | 2001-06-01 | 2002-05-24 | System zur freisetzung von aktivstoffen und wirkstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1392785A1 true EP1392785A1 (de) | 2004-03-03 |
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| Application Number | Title | Priority Date | Filing Date |
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| EP02743098A Withdrawn EP1392785A1 (de) | 2001-06-01 | 2002-05-24 | System zur freisetzung von aktivstoffen und wirkstoffen |
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| US (1) | US20040247895A1 (enExample) |
| EP (1) | EP1392785A1 (enExample) |
| JP (1) | JP2004530027A (enExample) |
| CN (1) | CN1286933C (enExample) |
| DE (1) | DE10126966A1 (enExample) |
| WO (1) | WO2002098998A1 (enExample) |
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| MY103969A (en) * | 1988-01-19 | 1993-10-30 | Kao Corp | Detergent composition containing perfume |
| DE19534980A1 (de) * | 1995-09-20 | 1997-03-27 | Inst Neue Mat Gemein Gmbh | Dünne SiO¶2¶-Folien, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19534764A1 (de) * | 1995-09-19 | 1997-03-20 | Inst Neue Mat Gemein Gmbh | Dünne SiO¶2¶-Folien, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US6017389A (en) * | 1995-09-19 | 2000-01-25 | Institute Fuer Neue Materialen Gemeinnuetzige Gmbh | Thin SiO2 films, a process for producing them and their use |
| DE19620668C1 (de) * | 1996-05-22 | 1997-09-11 | Feinchemie Gmbh Sebnitz | Thermisch härtbarer Mehrkomponenten-Lack |
| DE19805977A1 (de) * | 1998-02-13 | 1999-08-19 | Inst Neue Mat Gemein Gmbh | Photochrome Beschichtungszusammensetzung und damit beschichtete Substrate |
| DE19915377A1 (de) * | 1999-04-06 | 2000-10-12 | Inst Neue Mat Gemein Gmbh | Katalytische Zusammensetzung, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10021165A1 (de) * | 2000-04-29 | 2001-11-08 | Henkel Kgaa | System für die Freisetzung von Wirkstoffen |
-
2001
- 2001-06-01 DE DE10126966A patent/DE10126966A1/de not_active Ceased
-
2002
- 2002-05-24 CN CNB028132181A patent/CN1286933C/zh not_active Expired - Fee Related
- 2002-05-24 WO PCT/EP2002/005752 patent/WO2002098998A1/de not_active Ceased
- 2002-05-24 EP EP02743098A patent/EP1392785A1/de not_active Withdrawn
- 2002-05-24 JP JP2003502110A patent/JP2004530027A/ja not_active Withdrawn
-
2003
- 2003-12-01 US US10/725,067 patent/US20040247895A1/en not_active Abandoned
Non-Patent Citations (2)
| Title |
|---|
| None * |
| See also references of WO02098998A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE10126966A1 (de) | 2002-12-12 |
| WO2002098998A1 (de) | 2002-12-12 |
| US20040247895A1 (en) | 2004-12-09 |
| JP2004530027A (ja) | 2004-09-30 |
| CN1286933C (zh) | 2006-11-29 |
| CN1522286A (zh) | 2004-08-18 |
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