WO1996026704A1 - Adhesive for dental prostheses - Google Patents
Adhesive for dental prostheses Download PDFInfo
- Publication number
- WO1996026704A1 WO1996026704A1 PCT/GB1996/000164 GB9600164W WO9626704A1 WO 1996026704 A1 WO1996026704 A1 WO 1996026704A1 GB 9600164 W GB9600164 W GB 9600164W WO 9626704 A1 WO9626704 A1 WO 9626704A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition according
- camomile
- camomile extract
- composition
- preparation
- Prior art date
Links
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 46
- 239000000853 adhesive Substances 0.000 title claims abstract description 43
- 239000000203 mixture Substances 0.000 claims abstract description 47
- 239000000284 extract Substances 0.000 claims abstract description 45
- 238000002360 preparation method Methods 0.000 claims abstract description 21
- 239000003814 drug Substances 0.000 claims abstract description 4
- 239000006071 cream Substances 0.000 claims description 17
- 239000000470 constituent Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 239000000499 gel Substances 0.000 claims description 9
- 210000002200 mouth mucosa Anatomy 0.000 claims description 9
- 235000010469 Glycine max Nutrition 0.000 claims description 8
- 206010061218 Inflammation Diseases 0.000 claims description 8
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical class [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 8
- RGZSQWQPBWRIAQ-LSDHHAIUSA-N alpha-Bisabolol Natural products CC(C)=CCC[C@@](C)(O)[C@@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-LSDHHAIUSA-N 0.000 claims description 8
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 8
- 239000003921 oil Substances 0.000 claims description 8
- 235000019198 oils Nutrition 0.000 claims description 8
- 239000002674 ointment Substances 0.000 claims description 8
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 8
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 8
- RGZSQWQPBWRIAQ-CABCVRRESA-N (-)-alpha-Bisabolol Chemical compound CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-CABCVRRESA-N 0.000 claims description 7
- 239000001500 (2R)-6-methyl-2-[(1R)-4-methyl-1-cyclohex-3-enyl]hept-5-en-2-ol Substances 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 6
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical class CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims description 5
- 239000005662 Paraffin oil Substances 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 5
- 239000000661 sodium alginate Chemical class 0.000 claims description 5
- 235000010413 sodium alginate Nutrition 0.000 claims description 5
- 229940005550 sodium alginate Drugs 0.000 claims description 5
- 229940099259 vaseline Drugs 0.000 claims description 5
- 244000068988 Glycine max Species 0.000 claims description 4
- 235000019486 Sunflower oil Nutrition 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 239000000796 flavoring agent Substances 0.000 claims description 4
- 235000013355 food flavoring agent Nutrition 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- -1 polyoxymethylene Polymers 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 239000002600 sunflower oil Substances 0.000 claims description 4
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 3
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- 229920001577 copolymer Chemical class 0.000 claims description 3
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 229920002401 polyacrylamide Polymers 0.000 claims description 3
- 229920006324 polyoxymethylene Polymers 0.000 claims description 3
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 3
- 239000011118 polyvinyl acetate Substances 0.000 claims description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 description 26
- 238000012360 testing method Methods 0.000 description 24
- 230000001741 anti-phlogistic effect Effects 0.000 description 8
- 238000010586 diagram Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 3
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000013065 commercial product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 3
- 229940041616 menthol Drugs 0.000 description 3
- 235000019477 peppermint oil Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- JSNRRGGBADWTMC-UHFFFAOYSA-N (6E)-7,11-dimethyl-3-methylene-1,6,10-dodecatriene Chemical compound CC(C)=CCCC(C)=CCCC(=C)C=C JSNRRGGBADWTMC-UHFFFAOYSA-N 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 description 2
- VEUACKUBDLVUAC-UHFFFAOYSA-N [Na].[Ca] Chemical compound [Na].[Ca] VEUACKUBDLVUAC-UHFFFAOYSA-N 0.000 description 2
- KMOUJOKENFFTPU-UHFFFAOYSA-N cosmosiin Chemical compound OC1C(O)C(O)C(CO)OC1OC1=CC(O)=C2C(=O)C=C(C=3C=CC(O)=CC=3)OC2=C1 KMOUJOKENFFTPU-UHFFFAOYSA-N 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WTVHAMTYZJGJLJ-UHFFFAOYSA-N (+)-(4S,8R)-8-epi-beta-bisabolol Natural products CC(C)=CCCC(C)C1(O)CCC(C)=CC1 WTVHAMTYZJGJLJ-UHFFFAOYSA-N 0.000 description 1
- CXENHBSYCFFKJS-UHFFFAOYSA-N (3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraene Natural products CC(C)=CCCC(C)=CCC=C(C)C=C CXENHBSYCFFKJS-UHFFFAOYSA-N 0.000 description 1
- MJWZYBQLHJQQJJ-DOMZBBRYSA-N (6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one Chemical compound C1CC(C)=CC[C@H]1[C@@]1(C)OC(C)(C)C(=O)CC1 MJWZYBQLHJQQJJ-DOMZBBRYSA-N 0.000 description 1
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 1
- 229930189957 Bisabolol oxide Natural products 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical compound CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- ACBOFPQSBWBAQR-UHFFFAOYSA-N Cosmosiin Natural products OCC1OC(Oc2cc(O)c3C(=O)C=C(Oc3c2)c4cccc(O)c4)C(O)C(O)C1O ACBOFPQSBWBAQR-UHFFFAOYSA-N 0.000 description 1
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 description 1
- RDOFJDLLWVCMRU-UHFFFAOYSA-N Diisobutyl adipate Chemical compound CC(C)COC(=O)CCCCC(=O)OCC(C)C RDOFJDLLWVCMRU-UHFFFAOYSA-N 0.000 description 1
- 101100229963 Drosophila melanogaster grau gene Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 150000001545 azulenes Chemical class 0.000 description 1
- HHGZABIIYIWLGA-UHFFFAOYSA-N bisabolol Natural products CC1CCC(C(C)(O)CCC=C(C)C)CC1 HHGZABIIYIWLGA-UHFFFAOYSA-N 0.000 description 1
- 229940036350 bisabolol Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- PMRJYBALQVLLSJ-UHFFFAOYSA-N chamazulene Natural products CCC1=CC2=C(C)CCC2=CC=C1 PMRJYBALQVLLSJ-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229940031769 diisobutyl adipate Drugs 0.000 description 1
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 1
- 239000004174 erythrosine Substances 0.000 description 1
- 229930009668 farnesene Natural products 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 230000036074 healthy skin Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- PEFNSGRTCBGNAN-QNDFHXLGSA-N luteolin 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C=C(C=3C=C(O)C(O)=CC=3)OC2=C1 PEFNSGRTCBGNAN-QNDFHXLGSA-N 0.000 description 1
- SUTSVCLKBLJSPQ-UHFFFAOYSA-N luteolin 7-glucoside Natural products OC1C(O)C(O)C(CO)OC1C1=CC(O)=C2C(=O)C=C(C=3C=C(O)C(O)=CC=3)OC2=C1 SUTSVCLKBLJSPQ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 230000037311 normal skin Effects 0.000 description 1
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 1
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 1
- 235000005493 rutin Nutrition 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
- A61K6/35—Preparations for stabilising dentures in the mouth
Definitions
- the invention relates to a novel composition for use as an adhesive for dental prosthesis, the use thereof and a process for the preparation of a medicament for preventing or alleviating inflammation in the oral mucosa region.
- An aim of the present invention is to make available a prosthesis adhesive with improved antiphlogistic characteristics.
- compositions for use as an adhesive for dental prostheses, comprising an anti-phlogistically active amount of camomile extract.
- the composition in one alternative, can be in the form of a cream, ointment or gel and in this case the camomile extract is preferably in an oil-compatible preparation.
- the composition according to the invention contains 1 to 10, preferably 1 to 5, more preferably 1.5 to 3.5 and in particular approximately 2 wt. % camomile extract. The percentages are related to camomile constituents. When using camomile extracts with other active contents it would be necessary to adapt the camomile extract percentage in the adhesive.
- a dental prosthesis adhesive composition comprising
- flavouring agents optionally up to 2 wt. % of further additives such as flavouring agents, dyes and stabilizers.
- the base for the cream, ointment or gel in the composition comprises a substance chosen from the group constituted by paraffin oil, sunflower oil, soy oil (that is to say soya bean oil) , Vaseline and hydrophobic oleogels.
- the composition according to the invention can be in the form of a powder.
- the camomile extract is then preferably in a pulverulent preparation and in particularly preferred manner in a spray-dried preparation.
- a composition comprising 0.1 to 3.0, preferably 0.2 to 1.0 and in particular approximately 0.5 wt. % camomile extract, where the camomile extract is a preparation with approximately 50% camomile constituents.
- composition comprises
- flavouring agents up to 2 wt. %) , dyes (up to 0.1 wt. %) , stabilizers (up to 1 wt. %) and/or free-flow aids/diluents (up to 40 wt. %) .
- the active adhesive substance in a composition according to the invention is selected from the group comprising sodium carboxymethyl cellulose, sodium alginate, copolymer salts of methyl vinyl ether/maleic anhydride, polyvinyl acetate, polyvinyl pyrrolidone, hydroxyethyl cellulose, polyoxymethylene, polyacrylamides and mixtures thereof.
- a composition according to the invention may in addition have added to the adhesive at least one further addition of an antiphlogistically active substance, such as ⁇ -bisabolol.
- an antiphlogistically active substance such as ⁇ -bisabolol.
- camomile extract in an adhesive for dental prostheses for preventing or alleviating in lamination in the oral mucosa region. Still further according to the invention there is provided a process for the preparation of a medicament for preventing or alleviating inflammation in the oral mucosa region, in which an antiphlogistically active quantity of camomile extract is mixed with at least one active adhesive substance.
- the dental prosthesis adhesive compositions according to the invention have a better antiphlogistic action than the known adhesives which include only one constituent of camomile, ⁇ -bisabolol.
- the applicant does not wish to be bound by it, the hypothesis can be made that there is a synergistic action of the main constituents in the camomile extract, which surprisingly leads to said extract being antiphlogistically more active than oc- bisabolol alone.
- the main camomile constituents in addition to the ⁇ -bisabolol, which could play a further part here are azulenes (chamazulene, guajazulene) , further sesquiterpene derivatives (bisabolol oxides A, B and C, bisabolone oxide A) , and flavone glycosides (hyperoxide, rutin, luteolin-7-glucoside, apigenin-7- glucoside) , cumarin and farnesene.
- azulenes chamazulene, guajazulene
- bisabolol oxides A, B and C bisabolone oxide A
- flavone glycosides hyperoxide, rutin, luteolin-7-glucoside, apigenin-7- glucoside
- Fig. 1 A graph representing the capillary cutaneous circulation in the case of three adhesive creams according to the invention and untreated skin surface (control) , plotted against time.
- Fig. 2 A graph showing the capillary cutaneous circulation in the preferred adhesive cream according to the invention (HM 239) , two different comparison substances (HP1 and HP2) and the untreated skin surface (control) , plotted against time.
- FIG. 3 A diagram showing the confidential consumer test results with respect to the purchasing readiness of a product according to the invention and two comparison products.
- Fig. 4 A diagram showing the confidential consumer test results with regards to the product performance overall for a product according to the invention and two comparison products.
- Fig. 5 A diagram showing the confidential consumer test results relative to the general evaluation of a product according to the invention and two comparison products.
- Fig. 6 A diagram showing the confidential consumer test results with respect to the adhesive action of a product according to the invention and two comparison products.
- Fig. 7 A diagram comparing the drawability (in Newtons) for a product according to the invention and two comparison products.
- camomile extract is suitable within the scope of the present invention which has an antiphlogistic action, independently of the extracting agent and the camomile species (growing, part of the plant, cultivation area, etc. ) .
- the prerequisite for use in the adhesive composition according to the invention is that the camomile extract is brought in a form that is compatible with an end product application form.
- the hydrophilic solvents alcohols, glycols
- the preparation is carried out with more hydrophobic and therefore more oil-compatible solvents, such as e.g. soy oil (soya bean oil) or sunflower oil.
- soy oil soya bean oil
- sunflower oil e.g. soy oil (soya bean oil) or sunflower oil.
- the camomile extract used in Example 1 is Phytoconcentrol Camomile Oil-Soluble 2/066310 and that used in Example 2 is Neo-Extrapon camomile 2/060350 (both from Dragoco) .
- Other suitable extracts in oil-compatible preparation are e.g.
- camomile extracts LS 2416 G (soy oil, ie soya bean oil) , LS 2904 G (sunflower oil) or LS 3066 G (diisobutyl adipate) from Grau Aromatics (or corresponding products from Gattefosse GmbH e.g. Vegetol 4140).
- Example 1 Preparation of an adhesive cream according to the invention
- Camomile extract (oil-soluubbllee)) 3.00 2.00 Sodium carboxymethyl celluulloossee 15.00 15.00 ' (high viscosity) Sodium carboxymethyl cellulose (medium viscosity) 8.00 8.00 Poly(maleic acid/methyl vinyl ether) calcium / sodium salt 30.00 30.00
- Camomile extract (oil-solub >llee)) 2.00 1.00
- a Unimix mixer was pre-heated to 38°C. On reaching the temperature the weighed quantities of paraffin oil, melted Vaseline and optionally dye were fed in. This was followed by the addition of a mixture, prepared on the previous day, of peppermint oil and menthol, as well as the camomile extract. The mixture was then stirred for 3 minutes at 50 r.p.m.
- a formulation for an adhesive powder with a dried, pulverized camomile extract (having an approximately 50% camomile constituent content) was made up as follows:
- Neo-Extrapon camomile 2/060350 (Dragoco) or 50% sodium carboxymethyl cellulose DAB 49.7% sodium alginate DAB 0.3% Neo-Extrapon camomile 2/060350 (Dragoco) .
- the pulverized active substances were weighed in and transferred into a suitable container (e.g. conical worm mixture or helical belt mixer) . Mixing took place until all the active substances were completely homogeneously distributed.
- a suitable container e.g. conical worm mixture or helical belt mixer
- test preparations took place under occlusion, in order to come close to the conditions of the oral mucosa.
- a subsequent treatment took place after 3, 6, 9, 24 and 48 hours.
- the antiphlogistic activity was tested by measurements of capillary cutaneous circulation using the laser-Doppler flow meter. The lower the cutaneous circulation values the lower the erythema/irritation effects and the higher the antiphlogistic activity of the test product.
- Fig. 1 shows that even a 1% camomile extract content reveals a superior action compared with the control, but that an even more pronounced improvement results from increasing the content to 2%.
- a further increase in the camomile extract content to 3% leads to no further improvement of the antiphlogistic activity and in fact causes a slight deterioration compared with the product having a 2% camomile extract content.
- Fig. 2 compares the untreated skin surface (control) , products HP 1 and HP 2 and the product according to the invention with the optimum camomile extract content. The superior action of the adhesive according to the invention is very apparent.
- the confidential consumer test was carried out in such a way that the test products were concealed and in monadic manner by the consumer at home. The consumer was given brief instructions for use. Each group consisted of 60 persons, all of whom were adhesive cream or adhesive gel users.
- the results are shown in figs. 3 to 6 in the categories readiness to purchase, product performance overall, general evaluation and adhesive action.
- the product according to the invention with camomile extract revealed superior values in all categories. Of greatest interest are the adhesive action results of fig. 6.
- Fig. 7 compares the results of drawability test for the three aforementioned products.
- the test was performed in such a way that the test substance was placed on a plate, comprising a commercial prosthesis plastic material, weighed in and mixed with a clearly defined quantity of water.
- This plate was screwed into the tensile and co pressive force measuring instrument (Erichsen 391) .
- At the top was also screwed in a plate made from a commercial prosthesis plastic material, but which was additionally provided with an underlining material support which remained soft.
- the two plates were then compressed under clearly defined conditions. After a clearly defined time the force (in N) was measured, which was necessary for pulling apart the two plates.
- the read off value represents the drawability in N.
Abstract
A composition for use as an adhesive for dental prostheses, with an antiphlogistically active content of camomile extract, the use thereof and the preparation of a medicament on the basis thereof.
Description
Adhesive for Dental Prostheses
The invention relates to a novel composition for use as an adhesive for dental prosthesis, the use thereof and a process for the preparation of a medicament for preventing or alleviating inflammation in the oral mucosa region.
Although it is known that adhesives per se fulfil a preventative function, because they form a film on the prosthesis and in this way protect the sensitive mucosa against pressure points and inflammation, in the case of dental prosthesis wearers there are still pressure points and inflammation in the oral mucosa region. Thus, for reinforcing the preventative action there are prosthesis adhesives on the market, which contain as the anti- inflammatory active substance α-bisabolol which may be derived from camomile.
An aim of the present invention is to make available a prosthesis adhesive with improved antiphlogistic characteristics.
To this end, according to the invention there is provided a composition, for use as an adhesive for dental prostheses, comprising an anti-phlogistically active amount of camomile extract.
in one alternative, the composition can be in the form of a cream, ointment or gel and in this case the camomile extract is preferably in an oil-compatible preparation.
Preferably, the composition according to the invention contains 1 to 10, preferably 1 to 5, more preferably 1.5 to 3.5 and in particular approximately 2 wt. % camomile extract. The percentages are related to camomile constituents. When using camomile extracts with other active contents it would be necessary to adapt the camomile extract percentage in the adhesive.
Further according to the invention, there is provided a dental prosthesis adhesive composition comprising
i) 1 to 10 wt. % camomile extract,
ii) 30 to 60 wt. % of at least one active adhesive substance,
iii) 30 to 69 wt. % of a base for the cream, ointment or gel and
iv) optionally up to 2 wt. % of further additives such as flavouring agents, dyes and stabilizers.
Preferably the base for the cream, ointment or gel in the composition comprises a substance chosen from the group constituted by paraffin oil, sunflower oil, soy oil (that is to say soya bean oil) , Vaseline and hydrophobic oleogels.
In another alternative, the composition according to the invention can be in the form of a powder. The camomile extract is then preferably in a pulverulent preparation and in particularly preferred manner in a spray-dried preparation.
Further according to the invention, there is provided a composition comprising 0.1 to 3.0, preferably 0.2 to 1.0 and in particular approximately 0.5 wt. % camomile extract, where the camomile extract is a preparation with approximately 50% camomile constituents.
Preferably such a composition comprises
a) 0.1 to 3.0 wt. % camomile extract,
b) 30 to 99.9 wt. % of at least one active adhesive substance and
c) optionally further additives such as flavouring agents (up to 2 wt. %) , dyes (up to 0.1 wt. %) , stabilizers (up to 1 wt. %) and/or free-flow aids/diluents (up to 40 wt. %) .
It is preferable for the active adhesive substance in a composition according to the invention to be selected from the group comprising sodium carboxymethyl cellulose, sodium alginate, copolymer salts of methyl vinyl ether/maleic anhydride, polyvinyl acetate, polyvinyl pyrrolidone, hydroxyethyl cellulose, polyoxymethylene, polyacrylamides and mixtures thereof.
A composition according to the invention may in addition have added to the adhesive at least one further addition of an antiphlogistically active substance, such as α-bisabolol.
Further according to the invention , there is provided the use of camomile extract in an adhesive for dental prostheses for preventing or alleviating in lamination in the oral mucosa region.
Still further according to the invention there is provided a process for the preparation of a medicament for preventing or alleviating inflammation in the oral mucosa region, in which an antiphlogistically active quantity of camomile extract is mixed with at least one active adhesive substance.
It has surprisingly been found that the dental prosthesis adhesive compositions according to the invention have a better antiphlogistic action than the known adhesives which include only one constituent of camomile, α-bisabolol. Although the applicant does not wish to be bound by it, the hypothesis can be made that there is a synergistic action of the main constituents in the camomile extract, which surprisingly leads to said extract being antiphlogistically more active than oc- bisabolol alone. The main camomile constituents, in addition to the α-bisabolol, which could play a further part here are azulenes (chamazulene, guajazulene) , further sesquiterpene derivatives (bisabolol oxides A, B and C, bisabolone oxide A) , and flavone glycosides (hyperoxide, rutin, luteolin-7-glucoside, apigenin-7- glucoside) , cumarin and farnesene.
In addition, in a confidential consumer test it was found that unexpectedly the adhesive composition according to the invention with camomile extract was also better evaluated with respect to adhesion than other products. Finally, the superior drawability of the product according to the invention was established, which also indicates improved adhesion.
The invention is described in greater detail hereinafter by the following examples, which are in the form of preparation examples and test results concerning the anti-inflammatory/inflammation-preventing activity, as well as the improved adhesion of the adhesive composition according to the invention. In the drawings the figures are as follows:
Fig. 1 A graph representing the capillary cutaneous circulation in the case of three adhesive creams according to the invention and untreated skin surface (control) , plotted against time.
Fig. 2 A graph showing the capillary cutaneous circulation in the preferred adhesive cream according to the invention (HM 239) , two different comparison substances (HP1 and HP2) and the untreated skin surface (control) , plotted against time.
Fig. 3 A diagram showing the confidential consumer test results with respect to the purchasing readiness of a product according to the invention and two comparison products.
Fig. 4 A diagram showing the confidential consumer test results with regards to the product performance overall for a product according to the invention and two comparison products.
Fig. 5 A diagram showing the confidential consumer test results relative to the general evaluation of a product according to the invention and two comparison products.
Fig. 6 A diagram showing the confidential consumer test results with respect to the adhesive action of a product according to the invention and two comparison products.
Fig. 7 A diagram comparing the drawability (in Newtons) for a product according to the invention and two comparison products.
Before going into detail on the different exemplified formulations, we wish to point out that in general any camomile extract is suitable within the scope of the present invention which has an antiphlogistic action, independently of the extracting agent and the camomile species (growing, part of the plant, cultivation area, etc. ) .
The prerequisite for use in the adhesive composition according to the invention is that the camomile extract is brought in a form that is compatible with an end product application form.
This for example means that when used in the form of a cream, gel or ointment, the hydrophilic solvents (alcohols, glycols) are removed and that the preparation is carried out with more hydrophobic and therefore more oil-compatible solvents, such as e.g. soy oil (soya bean oil) or sunflower oil.
In the following examples, the camomile extract used in Example 1 is Phytoconcentrol Camomile Oil-Soluble 2/066310 and that used in Example 2 is Neo-Extrapon camomile 2/060350 (both from Dragoco) . Other suitable extracts in oil-compatible preparation are e.g. camomile extracts LS 2416 G (soy oil, ie soya bean oil) , LS 2904 G (sunflower oil) or LS 3066 G (diisobutyl adipate) from Grau Aromatics (or corresponding products from Gattefosse GmbH e.g. Vegetol 4140).
Example 1: Preparation of an adhesive cream according to the invention
The following tables 1 and 2 give exemplified formulations for an adhesive cream with camomile extract, the products with the designations VM 196, HM 239 and HM 347 are in the particularly preferred range for the camomile extract content. The given formulations were used for the subsequently described tests. The camomile extract used was present in a preparation with approximately 10% camomile constituents.
TABLE 1
Constituents VM.196 HM 239 Paraffin oil 31.88 32.88 Vaseline 12.00 12.00 Peppermint oil 0.10 0.10 Menthol 0.02 0.02
Camomile extract (oil-soluubbllee)) 3.00 2.00 Sodium carboxymethyl celluulloossee 15.00 15.00 ' (high viscosity) Sodium carboxymethyl cellulose (medium viscosity) 8.00 8.00
Poly(maleic acid/methyl vinyl ether) calcium / sodium salt 30.00 30.00
TABLE 2
Constituents HM 347 HM 349
Paraffin oil 30.375 32.075
Vaseline 14.50 13.80
Peppermint oil 0.10 0.10
Menthol 0.02 0.02
Dye E 127 0.005 0.005
Camomile extract (oil-solub >llee)) 2.00 1.00
Sodium carboyxmethyl celluloossee 15.00 15.00
(high viscosity)
Sodium carboxymethyl cellulose
(medium viscosity) 8.00 8.00
Poly(maleic acid/methyl vinyl ether) calcium sodium salt 30.00 30.00
The preparation of the corresponding adhesive creams in each case took place in the following way.
A Unimix mixer was pre-heated to 38°C. On reaching the temperature the weighed quantities of paraffin oil, melted Vaseline and optionally dye were fed in. This was followed by the addition of a mixture, prepared on the previous day, of peppermint oil and menthol, as well as the camomile extract. The mixture was then stirred for 3 minutes at 50 r.p.m.
This was followed by the addition of the pulverulent adhesive raw materials by filling connection and accompanied by stirring in the following order: poly(maleic acid/methyl vinyl ether) calcium sodium salt, sodium carboxymethyl cellulose (high viscosity) and sodium carboxymethyl cellulose (medium viscosity) .
After adding all the powder components the mixture was stirred for a further 60 minutes at 50 r.p.m. until all the constituents were homogeneously distributed.
Example 2: Preparation of an adhesive powder according to the invention
A formulation for an adhesive powder with a dried, pulverized camomile extract (having an approximately 50% camomile constituent content) was made up as follows:
99.5% sodium alginate DAB 0.5% Neo-Extrapon camomile 2/060350 (Dragoco) or 50% sodium carboxymethyl cellulose DAB 49.7% sodium alginate DAB 0.3% Neo-Extrapon camomile 2/060350 (Dragoco) .
The pulverized active substances were weighed in and transferred into a suitable container (e.g. conical worm mixture or helical belt mixer) . Mixing took place until all the active substances were completely homogeneously distributed.
Example 3: Testing the anti-inflammatory/inflammation- inhibiting activity of the adhesive to the invention
For the activity test described in greater detail hereinafter comparison took place between the adhesive creams prepared according to example 1, a standard commercial product (HP 1) , a commercial product with α- bisabolol (HP 2) and the untreated skin surface (control) .
Testing took place on volunteer test persons, under secrecy provisions, with a healthy skin. Using a solar simulator, irradiation took place until the erythema threshold was reached. Immediately following radiation the previously divided up test areas were treated with the formulations (control: untreated) .
Application of the test preparations took place under occlusion, in order to come close to the conditions of the oral mucosa. A subsequent treatment took place after 3, 6, 9, 24 and 48 hours.
The antiphlogistic activity was tested by measurements of capillary cutaneous circulation using the laser-Doppler flow meter. The lower the cutaneous circulation values the lower the erythema/irritation effects and the higher the antiphlogistic activity of the test product.
This process has been established as an investigation model for determining the antiphlogistic activity. It is possible to transfer the results from the normal skin to the oral mucosa, because as a result of easier resorption conditions in the oral mucosa, a reinforcement of the antiphlogistic properties is to be expected. The test results are compared in figs. 1 and 2.
Fig. 1 shows that even a 1% camomile extract content reveals a superior action compared with the control, but that an even more pronounced improvement results from increasing the content to 2%.
A further increase in the camomile extract content to 3% leads to no further improvement of the antiphlogistic activity and in fact causes a slight deterioration compared with the product having a 2% camomile extract content.
Fig. 2 compares the untreated skin surface (control) , products HP 1 and HP 2 and the product according to the invention with the optimum camomile extract content. The superior action of the adhesive according to the invention is very apparent.
Example 4: Testing the adhesion of the adhesive cream according to the invention
In the following tests comparisons took place between the standard adhesive cream product (HP 1) known from example 3, the commercial product with α-bisabolol (HP 2) known from example 3 and the product according to the invention (VP) (corresponding to product Hm 239 of example 3) in a confidential consumer test and in a drawability test.
The confidential consumer test was carried out in such a way that the test products were concealed and in monadic manner by the consumer at home. The consumer was given brief instructions for use. Each group consisted of 60 persons, all of whom were adhesive cream or adhesive gel users.
The evaluation scale extended from 1 to 5 and 5 represented the maximum number of points attainable. The results are shown in figs. 3 to 6 in the categories readiness to purchase, product performance overall, general evaluation and adhesive action.
The product according to the invention with camomile extract revealed superior values in all categories. Of greatest interest are the adhesive action results of fig. 6.
Fig. 7 compares the results of drawability test for the three aforementioned products. The test was performed in such a way that the test substance was placed on a plate, comprising a commercial prosthesis plastic material, weighed in and mixed with a clearly defined quantity of water. This plate was screwed into the tensile and co pressive force measuring instrument (Erichsen 391) . At the top was also screwed in a plate made from a commercial prosthesis plastic material, but which was additionally provided with an underlining material support which remained soft. The two plates were then compressed under clearly defined conditions. After a clearly defined time the force (in N) was measured, which was necessary for pulling apart the two plates. The read off value represents the drawability in N.
Claims
1. A composition for use as an adhesive for dental prosthesis, characterized by comprising an antiphlogistically active camomile extract.
2. A composition according to claim 1, in which the composition is in the form of a cream, ointment or gel.
3. A composition according to claim 1, in which the camomile extract is present in an oil-compatible preparation.
4. A composition according to claim 1, in which the content of camomile extract is 1 to 10 wt.%, based on a camomile extract in a preparation with approximately 10% camomile constituents.
5. A composition in the form of a cream, ointment or gel for use in denture fixing, comprising
i) 1 to 15 wt.% camomile extract, ii) 30 to 60 wt.% of at least one active adhesive substance, iii) 30 to 69 wt.% of a base for the cream, ointment or gel and iv) optionally up to 2 wt.% of further additives such as flavouring agents, dyes and stabilizers.
6. A composition according to one of the claim 2, characterized in that the base for the cream, ointment or gel is chosen from the group comprising paraffin oil, sunflower oil, soy oil (soya bean oil), Vaseline and hydrophobic oloegels.
7. A composition according to claim 5, in which the active adhesive substance is selected from the group comprising sodium carboxymethyl cellulose, sodium alginate, copolymer salts methyl vinyl ether/maleic anhydride, polyvinyl acetate, polyvinyl pyrrolidone, hydroxyethyl cellulose, polyoxymethylene, polyacrylamides and mixtures thereof.
8. A composition according to claim 1, in which the composition is a powder.
9. A composition according to claim 8, in which the camomile extract is a pulverulent preparation.
10. A composition according to claim 9, characterized in that the camomile extract is present in a spray-dried preparation.
11. A composition according to claim 8, in which the camomile extract is present in an amount of 0.1 to
3.0 wt.% , said extract being a preparation with approximately 50% camomile constituents.
12. A powder composition, for use in denture fixing, comprising
a) 0.1 to 3.0 wt.% camomile extract, b) 30 to 99.9 wt.% of at least one active adhesive substance and c) optionally further additives such as flavouring agents (up to 2 wt.%) , dyes (up to 0.1 wt.%) , stabilizers (up to 1 wt.%) and/or free-flow aids/diluents (up to 40 wt.%)
13. A composition according to claim 12, in which the active adhesive substance is selected from the group comprising sodium carboxymethyl cellulose, sodium
alginate, copolymer salts methyl vinyl ether/maleic anhydride, polyvinyl acetate, polyvinyl pyrrolidone, hydroxyethyl cellulose, polyoxymethylene, polyacrylamides and mixtures thereof.
14. A composition according to claim 1, in which the composition further contains at least one further anti¬ phlogistically active substance.
15. A composition according to claim 14, where the composition includes an additional amount of α-bisabolol.
16. Use of camomile extract in an adhesive for dental prostheses for preventing or alleviating inflammation in the oral mucosa region.
17. A process for the preparation of a medicament for preventing or alleviating inflammation in the oral mucosa region, characterized by mixing an antiphlogistically active quantity of camomile extract with at least one active adhesive substance.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ300239A NZ300239A (en) | 1995-02-27 | 1996-01-26 | Adhesive for dental prothesis with camomile extract to relieve inflammation |
| AU44924/96A AU711753B2 (en) | 1995-02-27 | 1996-01-26 | Adhesive for dental prostheses |
| EP96901047A EP0812179B1 (en) | 1995-02-27 | 1996-01-26 | Adhesive for dental prostheses |
| DE69632127T DE69632127T2 (en) | 1995-02-27 | 1996-01-26 | Adhesive for dental prostheses |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9503905.3 | 1995-02-27 | ||
| GB9503905A GB2299995B (en) | 1995-02-27 | 1995-02-27 | Adhesive for dental prostheses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1996026704A1 true WO1996026704A1 (en) | 1996-09-06 |
Family
ID=10770321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB1996/000164 WO1996026704A1 (en) | 1995-02-27 | 1996-01-26 | Adhesive for dental prostheses |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0812179B1 (en) |
| AU (1) | AU711753B2 (en) |
| DE (1) | DE69632127T2 (en) |
| ES (1) | ES2214526T3 (en) |
| GB (1) | GB2299995B (en) |
| HK (1) | HK1013957A1 (en) |
| IN (1) | IN187219B (en) |
| NZ (1) | NZ300239A (en) |
| WO (1) | WO1996026704A1 (en) |
| ZA (1) | ZA961203B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10302424B4 (en) * | 2002-01-25 | 2005-04-28 | Pms Handelskontor Gmbh | Adhesive for a denture |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9624618D0 (en) * | 1996-11-26 | 1997-01-15 | Nat Starch Chem Corp | Adhesive |
| US6223317B1 (en) | 1998-02-28 | 2001-04-24 | Micron Technology, Inc. | Bit synchronizers and methods of synchronizing and calculating error |
| EP3870150A1 (en) * | 2018-10-26 | 2021-09-01 | Viramal Limited | Mucoadhesive gel composition |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4894232A (en) * | 1987-04-28 | 1990-01-16 | Hoechst Aktiengesellschaft | Base for mucosal and denture adhesive pastes, a process for the preparation thereof, and pastes having this base |
| US4981875A (en) * | 1987-08-12 | 1991-01-01 | Bayer Aktiengesellschaft | Medicaments for the region of the oral cavity |
| WO1992010988A1 (en) * | 1990-12-21 | 1992-07-09 | Richardson-Vicks Inc. | Denture stabilizing compositions |
| DE4124050A1 (en) * | 1991-07-19 | 1993-01-21 | Robugen Gmbh | Antiphlogistic pharmaceutical based on camomile extract - contains a matricin-rich, dry, camomile extract |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE461378B (en) * | 1989-01-16 | 1990-02-12 | Fovarosi Tanacs Gyogyszertari | COMPOSITION FOR MEDICAL TREATMENT AND PREVENTION TO PREVENT PARADONTOPATHY |
-
1995
- 1995-02-27 GB GB9503905A patent/GB2299995B/en not_active Revoked
-
1996
- 1996-01-26 DE DE69632127T patent/DE69632127T2/en not_active Expired - Lifetime
- 1996-01-26 NZ NZ300239A patent/NZ300239A/en not_active IP Right Cessation
- 1996-01-26 AU AU44924/96A patent/AU711753B2/en not_active Expired
- 1996-01-26 WO PCT/GB1996/000164 patent/WO1996026704A1/en active IP Right Grant
- 1996-01-26 EP EP96901047A patent/EP0812179B1/en not_active Expired - Lifetime
- 1996-01-26 ES ES96901047T patent/ES2214526T3/en not_active Expired - Lifetime
- 1996-02-15 ZA ZA961203A patent/ZA961203B/en unknown
- 1996-02-16 IN IN259MA1996 patent/IN187219B/en unknown
-
1998
- 1998-12-23 HK HK98115171A patent/HK1013957A1/en not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4894232A (en) * | 1987-04-28 | 1990-01-16 | Hoechst Aktiengesellschaft | Base for mucosal and denture adhesive pastes, a process for the preparation thereof, and pastes having this base |
| US4981875A (en) * | 1987-08-12 | 1991-01-01 | Bayer Aktiengesellschaft | Medicaments for the region of the oral cavity |
| WO1992010988A1 (en) * | 1990-12-21 | 1992-07-09 | Richardson-Vicks Inc. | Denture stabilizing compositions |
| DE4124050A1 (en) * | 1991-07-19 | 1993-01-21 | Robugen Gmbh | Antiphlogistic pharmaceutical based on camomile extract - contains a matricin-rich, dry, camomile extract |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10302424B4 (en) * | 2002-01-25 | 2005-04-28 | Pms Handelskontor Gmbh | Adhesive for a denture |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2299995B (en) | 1999-06-30 |
| ZA961203B (en) | 1996-08-23 |
| ES2214526T3 (en) | 2004-09-16 |
| IN187219B (en) | 2002-03-02 |
| EP0812179A1 (en) | 1997-12-17 |
| AU4492496A (en) | 1996-09-18 |
| DE69632127D1 (en) | 2004-05-13 |
| EP0812179B1 (en) | 2004-04-07 |
| GB9503905D0 (en) | 1995-04-19 |
| GB2299995A (en) | 1996-10-23 |
| DE69632127T2 (en) | 2004-10-28 |
| NZ300239A (en) | 1998-08-26 |
| HK1013957A1 (en) | 1999-09-17 |
| AU711753B2 (en) | 1999-10-21 |
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