DE2433165C2 - N-Acetylglycin-l-menthylester, Verfahren zu seiner Herstellung und diesen Ester enthaltende Zahnpflegemittel - Google Patents
N-Acetylglycin-l-menthylester, Verfahren zu seiner Herstellung und diesen Ester enthaltende ZahnpflegemittelInfo
- Publication number
- DE2433165C2 DE2433165C2 DE2433165A DE2433165A DE2433165C2 DE 2433165 C2 DE2433165 C2 DE 2433165C2 DE 2433165 A DE2433165 A DE 2433165A DE 2433165 A DE2433165 A DE 2433165A DE 2433165 C2 DE2433165 C2 DE 2433165C2
- Authority
- DE
- Germany
- Prior art keywords
- ester
- acetylglycine
- menthyl
- menthol
- refreshing effect
- 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.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 title claims description 25
- -1 N-acetylglycine-1-menthyl ester Chemical compound 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 9
- 239000000551 dentifrice Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims 2
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 claims description 27
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 22
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 claims description 13
- 239000004471 Glycine Substances 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 9
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 8
- 229940041616 menthol Drugs 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 3
- 230000035807 sensation Effects 0.000 claims description 3
- 235000019615 sensations Nutrition 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 206010006784 Burning sensation Diseases 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 230000035597 cooling sensation Effects 0.000 claims 1
- 238000011835 investigation Methods 0.000 claims 1
- 230000005923 long-lasting effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 claims 1
- 210000003928 nasal cavity Anatomy 0.000 claims 1
- 210000001640 nerve ending Anatomy 0.000 claims 1
- 235000019477 peppermint oil Nutrition 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- 239000000606 toothpaste Substances 0.000 description 7
- 229940034610 toothpaste Drugs 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000002324 mouth wash Substances 0.000 description 6
- 229940051866 mouthwash Drugs 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 6
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 210000000214 mouth Anatomy 0.000 description 4
- 239000006072 paste Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 235000006679 Mentha X verticillata Nutrition 0.000 description 3
- 235000002899 Mentha suaveolens Nutrition 0.000 description 3
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000021736 acetylation Effects 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- 229940011037 anethole Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000003599 food sweetener Nutrition 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 3
- 238000005498 polishing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000003765 sweetening agent Substances 0.000 description 3
- 241000416162 Astragalus gummifer Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 240000006927 Foeniculum vulgare Species 0.000 description 2
- 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 2
- 235000019501 Lemon oil Nutrition 0.000 description 2
- 240000004760 Pimpinella anisum Species 0.000 description 2
- 235000012550 Pimpinella anisum Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- 239000004075 cariostatic agent Substances 0.000 description 2
- 235000017803 cinnamon Nutrition 0.000 description 2
- 239000010630 cinnamon oil Substances 0.000 description 2
- 239000010634 clove oil Substances 0.000 description 2
- 239000010501 lemon oil Substances 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 229940075560 sodium lauryl sulfoacetate Drugs 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- UAJTZZNRJCKXJN-UHFFFAOYSA-M sodium;2-dodecoxy-2-oxoethanesulfonate Chemical compound [Na+].CCCCCCCCCCCCOC(=O)CS([O-])(=O)=O UAJTZZNRJCKXJN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 description 1
- XGRSAFKZAGGXJV-UHFFFAOYSA-N 3-azaniumyl-3-cyclohexylpropanoate Chemical compound OC(=O)CC(N)C1CCCCC1 XGRSAFKZAGGXJV-UHFFFAOYSA-N 0.000 description 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- 235000003092 Artemisia dracunculus Nutrition 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000005696 Diammonium phosphate Substances 0.000 description 1
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 235000011173 Foeniculum vulgare subsp piperitum Nutrition 0.000 description 1
- 235000002782 Foeniculum vulgare var dulce Nutrition 0.000 description 1
- 235000002176 Foeniculum vulgare var vulgare Nutrition 0.000 description 1
- 240000001238 Gaultheria procumbens Species 0.000 description 1
- 235000007297 Gaultheria procumbens Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 240000004670 Glycyrrhiza echinata Species 0.000 description 1
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000015125 Sterculia urens Nutrition 0.000 description 1
- 240000001058 Sterculia urens Species 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 244000290333 Vanilla fragrans Species 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229940124277 aminobutyric acid Drugs 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003212 astringent agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- JUNWLZAGQLJVLR-UHFFFAOYSA-J calcium diphosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])([O-])=O JUNWLZAGQLJVLR-UHFFFAOYSA-J 0.000 description 1
- 229940043256 calcium pyrophosphate Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical class C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000010636 coriander oil Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- 235000019821 dicalcium diphosphate Nutrition 0.000 description 1
- 229960003887 dichlorophen Drugs 0.000 description 1
- QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 1
- PXLWOFBAEVGBOA-UHFFFAOYSA-N dihydrochalcone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=CC(C(=O)CC(O)C=2C=CC(O)=CC=2)=C1O PXLWOFBAEVGBOA-UHFFFAOYSA-N 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229940091249 fluoride supplement Drugs 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 1
- 229960004068 hexachlorophene Drugs 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 229940010454 licorice Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- AQMNWCRSESPIJM-UHFFFAOYSA-M sodium metaphosphate Chemical compound [Na+].[O-]P(=O)=O AQMNWCRSESPIJM-UHFFFAOYSA-M 0.000 description 1
- 229960004711 sodium monofluorophosphate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000009637 wintergreen oil 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
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Confectionery (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU68016A LU68016A1 (enExample) | 1973-07-13 | 1973-07-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2433165A1 DE2433165A1 (de) | 1975-01-30 |
| DE2433165C2 true DE2433165C2 (de) | 1983-05-26 |
Family
ID=19727400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2433165A Expired DE2433165C2 (de) | 1973-07-13 | 1974-07-10 | N-Acetylglycin-l-menthylester, Verfahren zu seiner Herstellung und diesen Ester enthaltende Zahnpflegemittel |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3991178A (enExample) |
| JP (1) | JPS5747904B2 (enExample) |
| CA (1) | CA1040214A (enExample) |
| CH (1) | CH605669A5 (enExample) |
| DE (1) | DE2433165C2 (enExample) |
| FR (1) | FR2236844B1 (enExample) |
| GB (1) | GB1464985A (enExample) |
| IT (1) | IT1050474B (enExample) |
| LU (1) | LU68016A1 (enExample) |
| NL (1) | NL7409302A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004043945A1 (de) * | 2004-09-11 | 2006-03-30 | Henkel Kgaa | Mund-, Zahn- und Zahnprotesenpflegemittel enthaltend die Plaquebildung inhibierende Substanzen |
| US7078066B2 (en) | 1997-09-18 | 2006-07-18 | Wm. Wrigley Jr. Company | Chewing gum containing physiological cooling agents and method of making |
Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS582229B2 (ja) * | 1977-04-11 | 1983-01-14 | 住友化学工業株式会社 | グリシンエステルの製法 |
| GB2114481B (en) * | 1982-02-16 | 1985-08-29 | Standard Telephones Cables Ltd | Improvements in hand tools |
| JPS59110521A (ja) * | 1982-12-17 | 1984-06-26 | Matsushita Electric Ind Co Ltd | ねじ締め機 |
| JPS59116177U (ja) * | 1983-01-28 | 1984-08-06 | 古河電気工業株式会社 | 締付箇所数計数装置付トルクレンチ |
| JPS59148273U (ja) * | 1983-03-25 | 1984-10-03 | 松下電器産業株式会社 | 動作回数カウント機構を備えた電動ドライバ− |
| DE3502830A1 (de) * | 1984-02-09 | 1985-08-14 | Colgate Palmolive Co | Zahnpflegemittelzusammensetzung |
| JPS62124081U (enExample) * | 1986-01-31 | 1987-08-06 | ||
| JPS6310074U (enExample) * | 1986-07-04 | 1988-01-22 | ||
| JPS63116275U (enExample) * | 1986-07-18 | 1988-07-27 | ||
| FR2603888B1 (fr) * | 1986-09-16 | 1990-12-21 | Panmedica Sa | Esters d'amino acides du trimethyl cyclohexanol, procede de preparation et utilisation comme medicaments |
| US5236946A (en) * | 1986-09-16 | 1993-08-17 | Panmedica S.A. | Amino acid esters of cycloaliphatic alcohols and their use in treating lipemic disorders |
| EP0310299A1 (en) * | 1987-09-28 | 1989-04-05 | The Procter & Gamble Company | Beta-amino acid ester derivatives of alcoholic actives having extended duration of activity |
| US4945347A (en) * | 1988-03-17 | 1990-07-31 | Perry John C | Motion and orientation responsive device for seismic, intrusion, and tilt alarms and the like |
| CA2054967C (en) * | 1990-11-06 | 1997-10-07 | Michael J. Greenberg | Enhanced flavors using menthone ketals |
| US5629013A (en) * | 1991-04-04 | 1997-05-13 | The Procter & Gamble Company | Chewable calcium carbonate antacid tablet compositions |
| US5244670A (en) * | 1991-04-04 | 1993-09-14 | The Procter & Gamble Company | Ingestible pharmaceutical compositions for treating upper gastrointestinal tract distress |
| DE4110973A1 (de) * | 1991-04-05 | 1992-10-08 | Haarmann & Reimer Gmbh | Mittel mit physiologischem kuehleffekt und fuer diese mittel geeignete wirksame verbindungen |
| US5286480A (en) * | 1992-06-29 | 1994-02-15 | The Procter & Gamble Company | Use of N-acetylated amino acid complexes in oral care compositions |
| AU5134893A (en) * | 1992-10-09 | 1994-05-09 | Procter & Gamble Company, The | Anaesthetic compositions |
| CA2161217A1 (en) * | 1993-04-30 | 1994-11-10 | Carmelita Macklin Russell | Coated pharmaceutical compositions |
| JPH0720267U (ja) * | 1993-09-17 | 1995-04-11 | 株式会社東日製作所 | トルクレンチ |
| DE69739369D1 (de) | 1997-09-18 | 2009-05-28 | Wrigley W M Jun Co | Kaugummizusammensetzung |
| US6455080B1 (en) | 1997-12-29 | 2002-09-24 | Wm. Wrigley Jr., Company | Chewing gum containing controlled release acyclic carboxamide and method of making |
| DE60031025T2 (de) | 1999-03-31 | 2007-05-24 | Firmenich S.A. | Verwendung von Cubebol als Aromastoff |
| WO2002024100A1 (en) * | 2000-09-21 | 2002-03-28 | Align Technology, Inc. | Concurrent tooth repositioning and substance delivery |
| KR100411205B1 (ko) * | 2001-08-27 | 2003-12-18 | 주식회사 태평양 | 멘톨 유도체 및 그의 제조방법 |
| US20040185093A1 (en) * | 2003-03-18 | 2004-09-23 | Szymczak Christopher E. | Compositions containing sucralose |
| US7025997B2 (en) * | 2003-09-24 | 2006-04-11 | International Flavors & Fragrances Inc. | Coolant plant extract compositions containing monomenthyl succinate |
| US8899976B2 (en) | 2004-09-24 | 2014-12-02 | Align Technology, Inc. | Release agent receptacle |
| AU2006302337C1 (en) | 2005-10-05 | 2013-04-04 | Intercontinental Great Brands Llc | Menthyl ester containing cooling compositions |
| EP1973421A2 (en) | 2005-12-23 | 2008-10-01 | Cadbury Adams USA LLC | Compositions providing a sensation substantially similar to that provided by menthol |
| EP2318356B1 (en) * | 2008-08-15 | 2015-03-11 | The Procter & Gamble Company | Synthesis of cyclohexane derivatives useful as sensates in consumer products |
| BRPI0917997A2 (pt) * | 2008-08-15 | 2015-11-17 | Procter & Gamble | solução de mentanocarboxamidas para uso em produtos destinados ao consumidor |
| AU2009318056B2 (en) | 2008-11-20 | 2014-07-24 | The Procter & Gamble Company | Personal care compositions providing enhanced cooling sensation |
| CN103153272A (zh) | 2010-07-19 | 2013-06-12 | 宝洁公司 | 包含精油化合物的衍生物的组合物以及在个人护理产品中的用途 |
| EP2621462B1 (en) | 2010-10-01 | 2020-02-12 | The Procter and Gamble Company | Oral care compositions with improved flavor |
| US20130042482A1 (en) | 2011-08-16 | 2013-02-21 | Valerie Jean Bradford | Skin Engaging Member Comprising An Anti-Irritation Agent |
| US8956593B2 (en) | 2011-09-01 | 2015-02-17 | The Procter & Gamble Co. | Oral care compositions with improved rheology |
| US20130315843A1 (en) | 2012-05-25 | 2013-11-28 | The Procter & Gamble Company | Composition for reduction of trpa1 and trpv1 sensations |
| KR20150050566A (ko) | 2012-09-28 | 2015-05-08 | 더 질레트 컴퍼니 | 하나 이상의 열탄성 센세이트를 포함하는 피부 맞닿음 면도 보조 부재 |
| WO2014052390A2 (en) | 2012-09-28 | 2014-04-03 | The Gillette Company | A skin engaging member comprising at least one thermally resilient sensate |
| US9884130B2 (en) | 2013-11-13 | 2018-02-06 | The Procter & Gamble Company | Compositions for delivery of oral comfort sensations |
| EP3110510A1 (en) | 2014-02-27 | 2017-01-04 | The Procter & Gamble Company | Oral care compositions with a reduced bitter taste perception |
| US20150272847A1 (en) | 2014-03-26 | 2015-10-01 | The Gillette Company | Skin Engaging Shaving Aid Comprising A Thermally Resilient Sensate And A TRPA1 Receptor Inhibitor |
| US20150273711A1 (en) | 2014-03-26 | 2015-10-01 | The Gillette Company | Razor Comprising A Molded Shaving Aid Composition Comprising A Thermally Resilient Sensate |
| RU2016138746A (ru) | 2014-04-23 | 2018-05-24 | Дзе Проктер Энд Гэмбл Компани | Циклогексанкарбоксамид с охлаждающими свойствами |
| WO2016025694A1 (en) | 2014-08-15 | 2016-02-18 | The Procter & Gamble Company | Oral care compositions with an enhanced sensory experience |
| AU2015301624B2 (en) | 2014-08-15 | 2018-10-18 | The Procter & Gamble Company | Dentifrice with incremental chemistries |
| RU2017102225A (ru) | 2014-08-15 | 2018-09-17 | Дзе Проктер Энд Гэмбл Компани | Композиции для ухода за полостью рта и схемы их применения |
| JP6626106B2 (ja) | 2014-11-26 | 2019-12-25 | ザ ジレット カンパニー リミテッド ライアビリティ カンパニーＴｈｅ Ｇｉｌｌｅｔｔｅ Ｃｏｍｐａｎｙ Ｌｌｃ | エチレン酢酸ビニルを含む皮膚係合部材 |
| US9951295B2 (en) | 2015-02-19 | 2018-04-24 | The Procter & Gamble Company | Compositions for deposition on biological surfaces |
| EP3280411B1 (en) | 2015-04-09 | 2020-02-19 | The Procter and Gamble Company | Reduction in cpc taste aversion by reducing cpc activation of trpa1 receptors, tprv1 receptors, or both |
| CA3000022A1 (en) | 2015-10-22 | 2017-04-27 | The Procter & Gamble Company | Synthesis of cyclohexane carboxamide derivatives useful as sensates in consumer products |
| CN108135812A (zh) | 2015-10-22 | 2018-06-08 | 宝洁公司 | 色谱分离的方法 |
| BR112018012071A2 (pt) | 2015-12-18 | 2018-11-27 | Procter & Gamble | síntese de derivados de éster de ciclo-hexano úteis como elementos sensoriais nos produtos destinados ao consumidor |
| AU2017240683B2 (en) | 2016-04-01 | 2020-01-16 | The Procter & Gamble Company | Oral care compositions containing potassium nitrate and peroxide |
| MX2018011991A (es) | 2016-04-01 | 2019-02-13 | Procter & Gamble | Composiciones para el cuidado bucal con una exhibicion de saborizante eficaz. |
| BR112018069957A2 (pt) | 2016-04-01 | 2019-02-05 | Procter & Gamble | composições para tratamento bucal contendo redes de gel e nitrato de potássio |
| EP3435958A1 (en) | 2016-04-01 | 2019-02-06 | The Procter and Gamble Company | Oral care compositions containing a gel network phase and potassium nitrate |
| BR112018069841A2 (pt) | 2016-04-01 | 2019-01-29 | Procter & Gamble | composições para tratamento bucal contendo uma fase de rede de gel |
| US20170334082A1 (en) | 2016-05-18 | 2017-11-23 | The Gillette Company Llc | Skin Engaging Member Comprising Ethylene Vinyl Acetate |
| CA3036897C (en) | 2016-10-25 | 2021-11-16 | The Procter & Gamble Company | Fibrous structures |
| US10745864B2 (en) | 2016-10-25 | 2020-08-18 | The Procter & Gamble Company | Differential pillow height fibrous structures |
| US20180117780A1 (en) | 2016-11-03 | 2018-05-03 | The Gillette Company Llc | Skin engaging member comprising ethylene vinyl acetate |
| EP3541476A1 (en) | 2016-11-17 | 2019-09-25 | The Gillette Company LLC | Skin engaging member comprising ethylene vinyl acetate and a fragrance |
| CN116710059A (zh) | 2020-09-28 | 2023-09-05 | 宝洁公司 | 包含啤酒花和风味剂的口腔护理组合物 |
| US20220370334A1 (en) | 2021-05-11 | 2022-11-24 | The Procter & Gamble Company | Oral Care Compositions Comprising Block Copolymer |
| CN115872881B (zh) * | 2022-11-14 | 2025-02-14 | 云南中烟工业有限责任公司 | 一种薄荷醇胺类化合物的合成方法及其在卷烟中的应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3793446A (en) * | 1969-05-14 | 1974-02-19 | Nickstadt Moeller Inc | Oral,nasal and labial compositions containing menthyl keto esters |
-
1973
- 1973-07-13 LU LU68016A patent/LU68016A1/xx unknown
-
1974
- 1974-07-10 DE DE2433165A patent/DE2433165C2/de not_active Expired
- 1974-07-10 NL NL7409302A patent/NL7409302A/xx not_active Application Discontinuation
- 1974-07-11 FR FR7424109A patent/FR2236844B1/fr not_active Expired
- 1974-07-11 GB GB3080674A patent/GB1464985A/en not_active Expired
- 1974-07-12 JP JP49080056A patent/JPS5747904B2/ja not_active Expired
- 1974-07-12 IT IT69234/74A patent/IT1050474B/it active
- 1974-07-12 CH CH965274A patent/CH605669A5/xx not_active IP Right Cessation
- 1974-07-15 US US05/488,856 patent/US3991178A/en not_active Expired - Lifetime
- 1974-07-15 CA CA204,786A patent/CA1040214A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7078066B2 (en) | 1997-09-18 | 2006-07-18 | Wm. Wrigley Jr. Company | Chewing gum containing physiological cooling agents and method of making |
| US7364761B2 (en) | 1997-09-18 | 2008-04-29 | Wm. Wrigley Jr. Company | Chewing gum containing physiological cooling agents and method of preparing |
| DE102004043945A1 (de) * | 2004-09-11 | 2006-03-30 | Henkel Kgaa | Mund-, Zahn- und Zahnprotesenpflegemittel enthaltend die Plaquebildung inhibierende Substanzen |
Also Published As
| Publication number | Publication date |
|---|---|
| CH605669A5 (enExample) | 1978-10-13 |
| FR2236844B1 (enExample) | 1978-02-03 |
| GB1464985A (en) | 1977-02-16 |
| NL7409302A (nl) | 1975-01-15 |
| JPS5747904B2 (enExample) | 1982-10-13 |
| US3991178A (en) | 1976-11-09 |
| CA1040214A (en) | 1978-10-10 |
| LU68016A1 (enExample) | 1975-04-11 |
| DE2433165A1 (de) | 1975-01-30 |
| IT1050474B (it) | 1981-03-10 |
| JPS5032149A (enExample) | 1975-03-28 |
| FR2236844A1 (enExample) | 1975-02-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2433165A1 (de) | N-acetylglycin-menthylester, verfahren zu seiner herstellung und seine verwendung | |
| DE69529160T2 (de) | Antiseptische zahnpasta | |
| DE2202535C3 (de) | Verwendung von p-Menthanderivaten | |
| DE2205255C3 (de) | N-substituierte p-Menthan-3-carbonsäureamide und sie enthaltende Mittel zur Stimulierung der Kaltrezeptoren des Nervensystems | |
| DE69830992T2 (de) | Desensibilisierende zahnpaste mit beschränkter astringenz | |
| DE2516610C2 (de) | Verbrauchsprodukt mit physiologischer Kühlwirkung | |
| DE69319276T2 (de) | Monophosphat enthaltende Zusammensetzung zur Verwendung in der Mundhöhle | |
| DE2366423C2 (de) | Verwendung von Carboxamiden als Kaltrezeptorstimulantien für Gegenstände oder Mittel mit einem Kühleffekt | |
| DE69314025T2 (de) | Zusammensetzungen mit kühleffekt | |
| DE69203391T2 (de) | Zinn-Verbindungen enthaltende Zahnpasten. | |
| DE69712054T2 (de) | Zahnpflegemittel gegen zahnsteinbildung enthaltend hochlösliche pyrophosphate | |
| DE4418796C5 (de) | Oral anwendbare und gegen Plaque und Gingivitis wirkende Zusammensetzungen | |
| DE2608226A1 (de) | Mittel mit physiologischer kuehlwirkung | |
| DE3217379A1 (de) | Aromahaltiges waessriges mundpflegemittel | |
| DE2501548A1 (de) | Mundbehandlungsmittel | |
| DE2339661A1 (de) | Orale, insbesondere kosmetische zubereitungen | |
| CH667992A5 (de) | Wasserfreie zahnpasta. | |
| DE69006069T2 (de) | Mittel für die orale Hygiene. | |
| DE3533492A1 (de) | Zahnbelag verhinderndes zahnpflegemittel | |
| AT390368B (de) | Stabiles zahnpflegemittel zur verhinderung von zahnbelag | |
| DE3102557A1 (de) | Keine flecken bildendes, gegen zahnfleischentzuendungen wirkendes mundpflegemittel | |
| DE2624504A1 (de) | Mittel oder gegenstand mit die kaltrezeptoren des menschlichen nervensystems stimulierender wirkung | |
| DE2944021A1 (de) | Erzeugnisse fuer die mundpflege, wie zahnpflege- und mundspuelmittel, und ihre herstellung | |
| DE2458562C2 (de) | Verbrauchsprodukt mit einer die Kaltrezeptoren des Nervensystems stimulierenden Verbindung | |
| DE69008153T2 (de) | Mundwasser und verfahren zur beseitigung des zahnsteins. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07C103/48 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |