CA1040214A - Organoleptic methyl-n-acetyglycinate - Google Patents
Organoleptic methyl-n-acetyglycinateInfo
- Publication number
- CA1040214A CA1040214A CA204,786A CA204786A CA1040214A CA 1040214 A CA1040214 A CA 1040214A CA 204786 A CA204786 A CA 204786A CA 1040214 A CA1040214 A CA 1040214A
- Authority
- CA
- Canada
- Prior art keywords
- ester
- menthol
- acetylglycine
- glycine
- sodium
- 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
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 claims abstract description 35
- 150000002148 esters Chemical class 0.000 claims abstract description 29
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 28
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229940041616 menthol Drugs 0.000 claims abstract description 18
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims abstract description 16
- 239000004471 Glycine Substances 0.000 claims abstract description 14
- 230000032050 esterification Effects 0.000 claims abstract description 5
- 238000005886 esterification reaction Methods 0.000 claims abstract description 5
- -1 menthol ester Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 abstract description 24
- 230000000694 effects Effects 0.000 abstract description 9
- 239000000551 dentifrice Substances 0.000 abstract description 5
- 230000021736 acetylation Effects 0.000 abstract description 4
- 238000006640 acetylation reaction Methods 0.000 abstract description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000796 flavoring agent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 210000000214 mouth Anatomy 0.000 description 6
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- 239000000606 toothpaste Substances 0.000 description 6
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- 239000006072 paste Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 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
- 150000001875 compounds Chemical class 0.000 description 4
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- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 230000001680 brushing effect Effects 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
- 235000013355 food flavoring agent Nutrition 0.000 description 3
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- MCNJOIMMYWLFBA-UHFFFAOYSA-N 2-dodecoxy-2-oxoethanesulfonic acid;sodium Chemical compound [Na].CCCCCCCCCCCCOC(=O)CS(O)(=O)=O MCNJOIMMYWLFBA-UHFFFAOYSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 206010006784 Burning sensation Diseases 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 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
- 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
- 235000006679 Mentha X verticillata Nutrition 0.000 description 2
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- 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
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- 229940011037 anethole Drugs 0.000 description 2
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- 235000017803 cinnamon Nutrition 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 239000000901 saccharin and its Na,K and Ca salt Substances 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
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000004094 surface-active agent 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
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 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
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 235000003092 Artemisia dracunculus Nutrition 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
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- 241000206575 Chondrus crispus Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 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
- 239000001836 Dioctyl sodium sulphosuccinate Substances 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- 244000303040 Glycyrrhiza glabra Species 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 229920000569 Gum karaya Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 244000018716 Impatiens biflora Species 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
- 235000019501 Lemon oil Nutrition 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 244000290333 Vanilla fragrans Species 0.000 description 1
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- 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
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- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 239000003212 astringent agent Substances 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 239000000625 cyclamic acid and its Na and Ca salt 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
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- 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
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- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- 235000011477 liquorice Nutrition 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229960001462 sodium cyclamate Drugs 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 229960000414 sodium fluoride Drugs 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
- 229960004711 sodium monofluorophosphate Drugs 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 229960002799 stannous fluoride Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
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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)
- Confectionery (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU68016A LU68016A1 (instruction) | 1973-07-13 | 1973-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1040214A true CA1040214A (en) | 1978-10-10 |
Family
ID=19727400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA204,786A Expired CA1040214A (en) | 1973-07-13 | 1974-07-15 | Organoleptic methyl-n-acetyglycinate |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3991178A (instruction) |
| JP (1) | JPS5747904B2 (instruction) |
| CA (1) | CA1040214A (instruction) |
| CH (1) | CH605669A5 (instruction) |
| DE (1) | DE2433165C2 (instruction) |
| FR (1) | FR2236844B1 (instruction) |
| GB (1) | GB1464985A (instruction) |
| IT (1) | IT1050474B (instruction) |
| LU (1) | LU68016A1 (instruction) |
| NL (1) | NL7409302A (instruction) |
Families Citing this family (70)
| 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 (instruction) * | 1986-01-31 | 1987-08-06 | ||
| JPS6310074U (instruction) * | 1986-07-04 | 1988-01-22 | ||
| JPS63116275U (instruction) * | 1986-07-18 | 1988-07-27 | ||
| US5236946A (en) * | 1986-09-16 | 1993-08-17 | Panmedica S.A. | Amino acid esters of cycloaliphatic alcohols and their use in treating lipemic disorders |
| FR2603888B1 (fr) * | 1986-09-16 | 1990-12-21 | Panmedica Sa | Esters d'amino acides du trimethyl cyclohexanol, procede de preparation et utilisation comme medicaments |
| 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 |
| EP0485170B1 (en) * | 1990-11-06 | 1995-09-13 | Wm. Wrigley Jr. Company | Enhanced flavors using menthone ketals |
| US5244670A (en) * | 1991-04-04 | 1993-09-14 | The Procter & Gamble Company | Ingestible pharmaceutical compositions for treating upper gastrointestinal tract distress |
| US5629013A (en) * | 1991-04-04 | 1997-05-13 | The Procter & Gamble Company | Chewable calcium carbonate antacid tablet compositions |
| 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 |
| US6627233B1 (en) | 1997-09-18 | 2003-09-30 | Wm. Wrigley Jr. Company | Chewing gum containing physiological cooling agents |
| RU2214721C2 (ru) | 1997-09-18 | 2003-10-27 | Вм. Ригли Дж. Компани | Способ производства жевательной резинки с физиологическими охлаждающими агентами (варианты), жевательная резинка по этому способу, композиция охлаждающего ароматизирующего вещества, жевательная резинка, включающая эту композицию, покрытая жевательная резинка (варианты), способ усиления вкусового воздействия покрытой жевательной резинки, способ покрытия жевательной резинки, композиция жевательной резинки |
| US6455080B1 (en) | 1997-12-29 | 2002-09-24 | Wm. Wrigley Jr., Company | Chewing gum containing controlled release acyclic carboxamide and method of making |
| ATE382270T1 (de) | 1999-03-31 | 2008-01-15 | Firmenich & Cie | Verwendung von cubebol als aromastoff |
| JP4460826B2 (ja) * | 2000-09-21 | 2010-05-12 | アライン テクノロジー， インコーポレイテッド | 同時の歯の再ポジショニングおよび物質送達のための方法およびシステム |
| 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 |
| DE102004043945A1 (de) * | 2004-09-11 | 2006-03-30 | Henkel Kgaa | Mund-, Zahn- und Zahnprotesenpflegemittel enthaltend die Plaquebildung inhibierende Substanzen |
| US8899976B2 (en) | 2004-09-24 | 2014-12-02 | Align Technology, Inc. | Release agent receptacle |
| CN103168899A (zh) | 2005-10-05 | 2013-06-26 | 卡夫食品环球品牌有限责任公司 | 包含薄荷酯的清凉组合物 |
| RU2398476C2 (ru) | 2005-12-23 | 2010-09-10 | КЭДБЕРИ АДАМС ЮЭсЭй ЛЛС | Композиции, обеспечивающие ощущения, аналогичные ощущениям, вызываемым ментолом |
| EP2318356B1 (en) * | 2008-08-15 | 2015-03-11 | The Procter & Gamble Company | Synthesis of cyclohexane derivatives useful as sensates in consumer products |
| WO2010019729A1 (en) * | 2008-08-15 | 2010-02-18 | The Procter & Gamble Company | Solution of menthane carboxamides for use in consumer products |
| MX2011005374A (es) | 2008-11-20 | 2011-06-06 | Procter & Gamble | Composiciones para el cuidado personal que proporcionan una sensacion refrescante mejorada. |
| WO2012012385A2 (en) | 2010-07-19 | 2012-01-26 | The Procter & Gamble Company | Compositions comprising derivatives of essential oil compounds and use in personal care products |
| US9937115B2 (en) | 2010-10-01 | 2018-04-10 | The Procter & 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 |
| CN103930091B (zh) | 2011-09-01 | 2016-03-02 | 宝洁公司 | 具有改善的流变特性的口腔护理组合物 |
| US20130315843A1 (en) | 2012-05-25 | 2013-11-28 | The Procter & Gamble Company | Composition for reduction of trpa1 and trpv1 sensations |
| BR112015006844B1 (pt) | 2012-09-28 | 2020-02-04 | Gillette Co | um elemento de contato com a pele que compreende ao menos uma substância sensibilizante termicamente resiliente |
| IN2015DN01435A (instruction) | 2012-09-28 | 2015-07-03 | Gillette Co | |
| 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 |
| CA2944160A1 (en) | 2014-04-23 | 2015-10-29 | The Procter & Gamble Company | Cyclohexanecarboxamide with cooling properties |
| RU2017103157A (ru) | 2014-08-15 | 2018-09-18 | Дзе Проктер Энд Гэмбл Компани | Средство ухода за зубами, обеспечивающее поэтапное химическое воздействие |
| EP3180090A1 (en) | 2014-08-15 | 2017-06-21 | The Procter and Gamble Company | Oral care compositions and regimens |
| CN106659650A (zh) | 2014-08-15 | 2017-05-10 | 宝洁公司 | 感官体验增强的口腔护理组合物 |
| BR112017011022B1 (pt) | 2014-11-26 | 2021-02-17 | The Gillette Company Llc | dispositivo de remoção de pelo e processo de formação de um membro de engate à pele |
| US9951295B2 (en) | 2015-02-19 | 2018-04-24 | The Procter & Gamble Company | Compositions for deposition on biological surfaces |
| MX2017012946A (es) | 2015-04-09 | 2018-01-30 | Procter & Gamble | Reduccion en la aversion del gusto mediada por cpc mediante la reduccion de la activacion de los receptores trpa1, los receptores tprv1, o ambos, mediada por cpc. |
| WO2017070414A1 (en) | 2015-10-22 | 2017-04-27 | The Procter & Gamble Company | Method of chromatographic separation |
| AU2016342264A1 (en) | 2015-10-22 | 2018-04-05 | The Procter & Gamble Company | Synthesis of cyclohexane carboxamide derivatives useful as sensates in consumer products |
| EP3390352A1 (en) | 2015-12-18 | 2018-10-24 | The Procter and Gamble Company | Synthesis of cyclohexane ester derivatives useful as sensates in consumer products |
| AU2017240033B2 (en) | 2016-04-01 | 2020-01-30 | The Procter & Gamble Company | Oral care compositions containing a gel network phase and potassium nitrate |
| CA3018799A1 (en) | 2016-04-01 | 2017-10-05 | The Procter & Gamble Company | Oral care compositions containing potassium nitrate and peroxide |
| EP3435959A1 (en) | 2016-04-01 | 2019-02-06 | The Procter and Gamble Company | Oral care compositions containing a gel network phase |
| AU2017240032B2 (en) | 2016-04-01 | 2019-07-18 | The Procter & Gamble Company | Oral care compositions containing gel networks and potassium nitrate |
| US10925820B2 (en) | 2016-04-01 | 2021-02-23 | The Procter & Gamble Company | Oral care compositions with an effective flavor display |
| US20170334082A1 (en) | 2016-05-18 | 2017-11-23 | The Gillette Company Llc | Skin Engaging Member Comprising Ethylene Vinyl Acetate |
| US10745864B2 (en) | 2016-10-25 | 2020-08-18 | The Procter & Gamble Company | Differential pillow height fibrous structures |
| WO2018081189A1 (en) | 2016-10-25 | 2018-05-03 | The Procter & Gamble Company | Fibrous structures |
| EP3535028A1 (en) | 2016-11-03 | 2019-09-11 | 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 |
| BR112023002550A2 (pt) | 2020-09-28 | 2023-04-04 | Procter & Gamble | Composição para tratamento bucal compreendendo lúpulo e flavorizante |
| JP2024516018A (ja) | 2021-05-11 | 2024-04-11 | ザ プロクター アンド ギャンブル カンパニー | ブロックコポリマーを含む口腔ケア組成物 |
| 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 NL NL7409302A patent/NL7409302A/xx not_active Application Discontinuation
- 1974-07-10 DE DE2433165A patent/DE2433165C2/de not_active Expired
- 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 IT IT69234/74A patent/IT1050474B/it active
- 1974-07-12 JP JP49080056A patent/JPS5747904B2/ja not_active Expired
- 1974-07-12 CH CH965274A patent/CH605669A5/xx not_active IP Right Cessation
- 1974-07-15 CA CA204,786A patent/CA1040214A/en not_active Expired
- 1974-07-15 US US05/488,856 patent/US3991178A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1464985A (en) | 1977-02-16 |
| DE2433165A1 (de) | 1975-01-30 |
| LU68016A1 (instruction) | 1975-04-11 |
| US3991178A (en) | 1976-11-09 |
| IT1050474B (it) | 1981-03-10 |
| NL7409302A (nl) | 1975-01-15 |
| JPS5032149A (instruction) | 1975-03-28 |
| DE2433165C2 (de) | 1983-05-26 |
| CH605669A5 (instruction) | 1978-10-13 |
| FR2236844A1 (instruction) | 1975-02-07 |
| FR2236844B1 (instruction) | 1978-02-03 |
| JPS5747904B2 (instruction) | 1982-10-13 |
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