JPH0631398B2 - Reserving agent for fragrance - Google Patents
Reserving agent for fragranceInfo
- Publication number
- JPH0631398B2 JPH0631398B2 JP20434784A JP20434784A JPH0631398B2 JP H0631398 B2 JPH0631398 B2 JP H0631398B2 JP 20434784 A JP20434784 A JP 20434784A JP 20434784 A JP20434784 A JP 20434784A JP H0631398 B2 JPH0631398 B2 JP H0631398B2
- Authority
- JP
- Japan
- Prior art keywords
- fragrance
- glucopyranose
- ether compound
- galactopyranose
- linalyl
- 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 - Lifetime
Links
- 239000003205 fragrance Substances 0.000 title claims description 15
- 239000003795 chemical substances by application Substances 0.000 title description 9
- -1 ether compound Chemical class 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 235000000346 sugar Nutrition 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 10
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 8
- 230000014759 maintenance of location Effects 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- 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 6
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 6
- 229960003082 galactose Drugs 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- 230000009965 odorless effect Effects 0.000 description 6
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 5
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 4
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229930182830 galactose Natural products 0.000 description 4
- 229930007744 linalool Natural products 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000007933 dermal patch Substances 0.000 description 3
- 229940041616 menthol Drugs 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ZCHHRLHTBGRGOT-SNAWJCMRSA-N (E)-hex-2-en-1-ol Chemical compound CCC\C=C\CO ZCHHRLHTBGRGOT-SNAWJCMRSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- PRNCMAKCNVRZFX-UHFFFAOYSA-N 3,7-dimethyloctan-1-ol Chemical compound CC(C)CCCC(C)CCO PRNCMAKCNVRZFX-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 2
- 239000005792 Geraniol Substances 0.000 description 2
- FPCCDPXRNNVUOM-UHFFFAOYSA-N Hydroxycitronellol Chemical compound OCCC(C)CCCC(C)(C)O FPCCDPXRNNVUOM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 229960002903 benzyl benzoate Drugs 0.000 description 2
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000000484 citronellol Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229940113087 geraniol Drugs 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- CZVXBFUKBZRMKR-UHFFFAOYSA-N lavandulol Chemical compound CC(C)=CCC(CO)C(C)=C CZVXBFUKBZRMKR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
- HZVFRKSYUGFFEJ-YVECIDJPSA-N (2r,3r,4s,5r)-7-phenylhept-6-ene-1,2,3,4,5,6-hexol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=CC1=CC=CC=C1 HZVFRKSYUGFFEJ-YVECIDJPSA-N 0.000 description 1
- NWXADGGHXYSLSP-IYWMVGAKSA-N (3s,4s,5s,6r)-1,8-diphenylocta-1,7-diene-2,3,4,5,6,7-hexol Chemical compound OC([C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=CC=1C=CC=CC=1)=CC1=CC=CC=C1 NWXADGGHXYSLSP-IYWMVGAKSA-N 0.000 description 1
- 239000001306 (7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-ol Substances 0.000 description 1
- 239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 description 1
- CZVXBFUKBZRMKR-JTQLQIEISA-N (R)-lavandulol Natural products CC(C)=CC[C@@H](CO)C(C)=C CZVXBFUKBZRMKR-JTQLQIEISA-N 0.000 description 1
- JVTXOMXEPFDMHB-UHFFFAOYSA-N 1-cyclohexylpropan-1-ol Chemical compound CCC(O)C1CCCCC1 JVTXOMXEPFDMHB-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- ROKSAUSPJGWCSM-UHFFFAOYSA-N 2-(7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)ethanol Chemical compound C1C2C(C)(C)C1CC=C2CCO ROKSAUSPJGWCSM-UHFFFAOYSA-N 0.000 description 1
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 description 1
- JRTBBCBDKSRRCY-UHFFFAOYSA-N 3,7-dimethyloct-6-en-3-ol Chemical compound CCC(C)(O)CCC=C(C)C JRTBBCBDKSRRCY-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- AJXRCDRDJCJBHG-UULXWRTPSA-N C(C)(C=C)(CCC=C(C)C)C1(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)C(O)=O Chemical compound C(C)(C=C)(CCC=C(C)C)C1(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)C(O)=O AJXRCDRDJCJBHG-UULXWRTPSA-N 0.000 description 1
- UBIVAKLKUIYYCU-DLYYPDDFSA-N CC(C)=CCCC(C)(OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1OC(C)(CCC=C(C)C)C=C)C=C Chemical compound CC(C)=CCCC(C)(OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1OC(C)(CCC=C(C)C)C=C)C=C UBIVAKLKUIYYCU-DLYYPDDFSA-N 0.000 description 1
- AMGCPJZUTQERJP-LIPWGPIPSA-N CC(C)=CCCC(C)(OC1O[C@H](CO)[C@@H](O)[C@H](OC(C)(CCC=C(C)C)C=C)[C@H]1OC(C)(CCC=C(C)C)C=C)C=C Chemical compound CC(C)=CCCC(C)(OC1O[C@H](CO)[C@@H](O)[C@H](OC(C)(CCC=C(C)C)C=C)[C@H]1OC(C)(CCC=C(C)C)C=C)C=C AMGCPJZUTQERJP-LIPWGPIPSA-N 0.000 description 1
- VHDQKGSRDHPXFF-MXANONMOSA-N CC(C)=CCCC(C)(OC[C@H]1OC(OC(C)(CCC=C(C)C)C=C)[C@H](OC(C)(CCC=C(C)C)C=C)[C@@H](OC(C)(CCC=C(C)C)C=C)[C@@H]1OC(C)(CCC=C(C)C)C=C)C=C Chemical compound CC(C)=CCCC(C)(OC[C@H]1OC(OC(C)(CCC=C(C)C)C=C)[C@H](OC(C)(CCC=C(C)C)C=C)[C@@H](OC(C)(CCC=C(C)C)C=C)[C@@H]1OC(C)(CCC=C(C)C)C=C)C=C VHDQKGSRDHPXFF-MXANONMOSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-CBPJZXOFSA-N D-Gulose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-CBPJZXOFSA-N 0.000 description 1
- WQZGKKKJIJFFOK-WHZQZERISA-N D-aldose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-WHZQZERISA-N 0.000 description 1
- WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- KEVYVLWNCKMXJX-ZCNNSNEGSA-N Isophytol Natural products CC(C)CCC[C@H](C)CCC[C@@H](C)CCC[C@@](C)(O)C=C KEVYVLWNCKMXJX-ZCNNSNEGSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VSOAQEOCSA-N L-altropyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-VSOAQEOCSA-N 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 description 1
- BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229930002886 farnesol Natural products 0.000 description 1
- 229940043259 farnesol Drugs 0.000 description 1
- 210000000245 forearm Anatomy 0.000 description 1
- CCCXGQLQJHWTLZ-UHFFFAOYSA-N geranyl linalool Natural products CC(=CCCC(=CCCCC(C)(O)CCC=C(C)C)C)C CCCXGQLQJHWTLZ-UHFFFAOYSA-N 0.000 description 1
- IQDXAJNQKSIPGB-HQSZAHFGSA-N geranyllinalool Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(C)(O)C=C IQDXAJNQKSIPGB-HQSZAHFGSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- MOTOHONMGNMXQA-UHFFFAOYSA-N hexan-1-ol hydrobromide Chemical compound Br.CCCCCCO MOTOHONMGNMXQA-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- DUNCVNHORHNONW-UHFFFAOYSA-N myrcenol Chemical compound CC(C)(O)CCCC(=C)C=C DUNCVNHORHNONW-UHFFFAOYSA-N 0.000 description 1
- 229930008383 myrcenol Natural products 0.000 description 1
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
Description
【発明の詳細な説明】 （発明の技術分野） 本発明は後記の一般式で表わされるエーテル化合物の少
なくとも一つを香料に有効成分として含有する香料用保
留剤に関する。TECHNICAL FIELD OF THE INVENTION The present invention relates to a perfume retention agent containing at least one ether compound represented by the following general formula in a perfume as an active ingredient.
（従来技術および問題点） 従来より天然あるいは合成の有効物質を用いて優れた香
料を調香するときには、所望の香気を持続させるために
有香物質の保留性を調整する各種の保留剤が香料に有効
成分として配合利用されている。(Prior Art and Problems) Conventionally, when an excellent fragrance is perfused with a natural or synthetic effective substance, various holding agents for adjusting the holding property of the fragrant substance in order to maintain a desired fragrance are fragrances. Is used as an active ingredient.
この保留剤としては、通常ジエチルフタレート，ベンジ
ルベンゾエート，トリエチルシトレート，イソプロピル
ミリステート，プロピレングリコール等が利用されてい
るが、いずれもそのもの自身に匂いがあったり、充分な
保留性が得られなかったり、価格が高かったりして、利
用に関して、おのずと制限が生じ、また保留剤として充
分に満足のいくものではなかつた。Diethyl phthalate, benzyl benzoate, triethyl citrate, isopropyl myristate, propylene glycol, etc. are usually used as this retaining agent, but they all have an odor or cannot retain sufficient retaining ability. However, due to the high price, there were naturally restrictions on the use, and it was not sufficiently satisfactory as a holding agent.
（発明の開示） 本発明者等は、上記の事情に鑑み鋭意研究した結果、６
炭糖と、炭素数４〜２０の飽和一価アルコールあるいは
不飽和一価アルコール（但し、芳香族化合物を除く）と
を縮合反応して得られるエーテル化合物（後記一般式で
表わされるエーテル化合物）は、無臭で化学的にも安定
であると共に皮膚に対して刺激性も無く、香料に有効成
分として含有すると顕著な保留効果を発現することを見
出し、本発明を完成した。(Disclosure of the Invention) As a result of intensive research conducted by the present inventors in view of the above circumstances, 6
An ether compound (ether compound represented by the following general formula) obtained by condensation reaction of a carbon sugar and a saturated monohydric alcohol or an unsaturated monohydric alcohol (excluding aromatic compounds) having 4 to 20 carbon atoms is They have found that they are odorless, chemically stable and non-irritating to the skin, and that when they are contained in a fragrance as an active ingredient, a remarkable retention effect is exhibited, and the present invention has been completed.
（発明の目的） 本発明の目的は、無臭で化学的にも安定であると共に皮
膚安全性および保留効果の高い優れた香料用保留剤を提
供することにある。(Object of the Invention) An object of the present invention is to provide an excellent perfume retention agent that is odorless, chemically stable, and has high skin safety and retention effect.
（発明の構成） Ｃ６ＨｘＯｙ−（ＯＲ）ｚ（式中で、 Ｃ６ＨｘＯｙは環状６炭糖残基、Ｒは炭素数４〜２０の
炭化水素基を示し（ｘ＋ｚ＝１２、ｙ＋ｚ＝６、ｚ＝１
〜５で、Ｒが芳香環の場合を除く。）で表されるエーテ
ル化合物の少なくとも一つを有効成分として香料に配合
し、その配合量が５〜７０重量％であることを特徴とす
る香料用保留剤である。(Configuration of the Invention) C 6 H x O y - (OR) z ( in the formula, C 6 H x O y cyclic hexose residue, R represents a hydrocarbon group having 4 to 20 carbon atoms (x + z = 12, y + z = 6, z = 1
Except when R is an aromatic ring. ) At least one of the ether compounds represented by the formula (1) is blended into the perfume as an active ingredient, and the blending amount is 5 to 70% by weight.
（構成の具体的な説明） 本発明に係る前記一般式で表わされるエーテル化合物
は、通常の合成（製造）方法で得られる。例えば６炭糖
の糖類に水素化ナトリウムを作用させたものと炭素数が
４〜２０の飽和あるいは不飽和の一価アルコール類（但
し、芳香族化合物を除く）の水酸基を臭素化したものと
を縮合反応させて得られる。(Specific Description of Structure) The ether compound represented by the above general formula according to the present invention can be obtained by a usual synthesis (manufacturing) method. For example, saccharides of 6-carbon sugars reacted with sodium hydride and saturated or unsaturated monohydric alcohols having 4 to 20 carbon atoms (excluding aromatic compounds) with brominated hydroxyl groups It is obtained by a condensation reaction.
前記の糖類は、５炭糖ではキシロース、アラビノース等
が適用され、また６炭糖ではグルコース、ガラクトー
ス、マンノース、アロース、アルトロース、グロース、
インドース、タロース等が適用される。特にグルコー
ス、ガラクトース、キシロース等は安価にして容易に入
手可能なもので好適である。As the above-mentioned saccharides, xylose, arabinose and the like are applied to 5-carbon sugars, and glucose, galactose, mannose, allose, altrose, gulose, and 6-carbon sugars are applied.
Indose, talose, etc. are applied. Particularly, glucose, galactose, xylose and the like are preferable because they are inexpensive and easily available.
前記の炭素数が４〜２０の飽和あるいは不飽和の一価ア
ルコール類は、例えば直鎖状の一価アルコールでは、ア
ルミアルコール、イソアミルコール、シス−８−ヘキセ
ノール、オクタノール、ノナノール、１−オクテン−８
−オール、ヘプタノール、ブタノール、トランス−２−
ヘキセノール、ヘキサノール等が適用され、側鎖状の一
価アルコールでは、８−メチルブタノール、２−ジメチ
ルプロパノール、２−メチルプロパノール、２−メチル
ブタノール、リナロール、ゲラニオール、シトロネロー
ル、ネロール、ヒドロキシシトロネロール、ジヒドロリ
ナロール、テトラヒドロリナロール、ジヒドロゲラニオ
ール、テトラヒドロゲラニオール、ファルネソール、ネ
ロリドール、フィトール、イソフィトール、ゲラニルリ
ナロール、ラバンジュロール、ミルセノール、トリエチ
ルシトレート等が適用され、更に環状の一価アルコール
では、４−ｔ−ブチルシクロヘキサノール、メントー
ル、ボルネオール、シクロヘキシルプロパノール、ノポ
ール、サンタロール（α、β−）、ターピネオール等が
適用される。Examples of the saturated or unsaturated monohydric alcohol having 4 to 20 carbon atoms include, for example, linear monohydric alcohols such as aluminum alcohol, isoamylchol, cis-8-hexenol, octanol, nonanol, and 1-octene-. 8
-Ol, heptanol, butanol, trans-2-
Hexenol, hexanol, etc. are applied, and as side chain monohydric alcohols, 8-methylbutanol, 2-dimethylpropanol, 2-methylpropanol, 2-methylbutanol, linalool, geraniol, citronellol, nerol, hydroxycitronellol, dihydrolinalool. , Tetrahydrolinalool, dihydrogeraniol, tetrahydrogeraniol, farnesol, nerolidol, phytol, isophytol, geranyllinalool, lavandulol, myrcenol, triethylcitrate, etc. are applied. Cyclohexanol, menthol, borneol, cyclohexyl propanol, nopol, santalol (α, β-), terpineol and the like are applied.
前記の糖類と一価のアルコール類とを縮合反応して得ら
れる本発明のエーテル化合物（前記一般式で表わされる
エーテル化合物）は、糖類における水酸基の数に対応し
て、６炭糖では一価アルコールの１置換体から５置換体
のエーテル化合物が存在する。The ether compound of the present invention (ether compound represented by the above general formula) obtained by condensation reaction of the above-mentioned saccharide and monohydric alcohol corresponds to the number of hydroxyl groups in the saccharide and is monovalent in 6-carbon sugar. There are 1- to 5-substituted ether compounds of alcohols.
本発明の前記一般式で表わされるエーテル化合物として
は、例えば、グルコースとリナロールより得られるモノ
−Ｏ−（リナリル）−グルコピラノース、ジ−Ｏ−（リ
ナリル）−グルコピラノース、トリ−Ｏ−（リナリル）
−グルコピラノース、テトラ−Ｏ−（リナリル）−グル
コピラノース、ペンタ−Ｏ−（リナリル）−グルコピラ
ノース、ガラクトースとゲラニオールから得られるモノ
−Ｏ−（ゲラニル）−ガラクトピラノース、ジ−Ｏ−
（ゲラニル）−ガラクトピラノース、トリ−Ｏ−（ゲラ
ニル）−ガラクトピラノース、テトラ−Ｏ−（ゲラニ
ル）−ガラクトピラノース、ペンタ−Ｏ−（ゲラニル）
−ガラクトピラノース、キシロースとメントールより得
られるモノ−Ｏ−（メンチル）−キシロピラノース、ジ
−Ｏ−（メンチル）−キシロピラノース、トリ−Ｏ−
（メンチル）キシロピラノース、テトラ−Ｏ−（メンチ
ル）−キシロピラノース、等が特に好ましいものとして
例示される。但しこれらのものに限定されない。Examples of the ether compound represented by the above general formula of the present invention include mono-O- (linalyl) -glucopyranose, di-O- (linalyl) -glucopyranose, and tri-O- (linalyl) obtained from glucose and linalool. )
-Glucopyranose, tetra-O- (linalyl) -glucopyranose, penta-O- (linalyl) -glucopyranose, mono-O- (geranyl) -galactopyranose obtained from galactose and geraniol, di-O-
(Geranyl) -galactopyranose, tri-O- (geranyl) -galactopyranose, tetra-O- (geranyl) -galactopyranose, penta-O- (geranyl)
-Galactopyranose, mono-O- (menthyl) -xylopyranose obtained from xylose and menthol, di-O- (menthyl) -xylopyranose, tri-O-
(Mentyl) xylopyranose, tetra-O- (menthyl) -xylopyranose, and the like are exemplified as particularly preferable ones. However, it is not limited to these.
前記一般式で表わされるエーテル化合物の少なくとも一
つの香料中に有効成分として含有（配合）する量は、組
成物の総量を基準として５〜７０重量％（以下重量％を
ｗｔ％と略記する）である。The amount of the ether compound represented by the general formula contained (blended) in at least one fragrance as an active ingredient is 5 to 70% by weight (hereinafter, the weight% is abbreviated as wt%) based on the total amount of the composition. is there.
（発明の実施例） 以下、実施例に基づいて本発明を詳説する。尚、本発明
は実施例の記載に限定されるものではない。(Examples of the Invention) Hereinafter, the present invention will be described in detail based on examples. The present invention is not limited to the description of the embodiments.
実施例に記載した安定性試験、ヒト皮膚貼布試験、保留
効果試験は、下記の通りである。The stability test, human skin patch test, and retention effect test described in the examples are as follows.
(1)安定性試験 試料１ｗｔ％、エタノール４９ｗｔ％、５０ｗｔ％とか
らなる組成の溶液を調製し、この溶液をガラス瓶に収納
して太陽光に１ケ月間被曝した試験品と、冷暗室（５
℃）に１ケ月間保存した同一溶液の対照品との臭の差異
を評価した。(1) Stability test A solution having a composition of 1 wt% sample, 49 wt% ethanol, and 50 wt% ethanol was prepared, and the solution was placed in a glass bottle and exposed to sunlight for 1 month.
The difference in odor from the control product of the same solution stored for 1 month at (° C) was evaluated.
下記第１表の判定基準に従い、調香師からなる判定者５
名による官能テストにより判定し、その結果を○、△、
×で示した。A judge 5 consisting of a perfumer according to the criteria shown in Table 1 below.
Judgment by sensory test by name, the result is ○, △,
It is shown by x.
(2)ヒト皮膚貼布試験 被検者２５名の前腕屈側部皮膚に、試料0.05ｇを直径1.
0cmの円型のリント布のついた貼布試験用絆創膏を用い
て２４時間の閉塞貼布した。次いで、下記第２表の判定
基準に従って、絆創膏除去１時間後、２４時間後の判定
を実施した。判定結果は、反応の強い方の評価を採用
し、被検者２５名のうち評価が（±）以上と判定された
人の数で示した。 (2) Human skin patch test Twenty-five subjects had skin on the flexion side of the forearm with a sample of 0.05 g in diameter 1.
An occlusion patch was applied for 24 hours using a patch test plaster with a 0 cm circular lint cloth. Then, according to the criteria shown in Table 2 below, the determination was carried out 1 hour after removing the adhesive bandage and 24 hours later. The evaluation results were evaluated by adopting the evaluation with the stronger reaction, and indicated by the number of people among the 25 subjects who were evaluated as (±) or higher.
(3)保留効果試験 第３表に示す有香物質１０種からなるモデル調合香料７
０ｗｔ％と試料３０ｗｔ％とを均一に溶解混合した試験
品を調製し、匂い紙（９cm×９cm2.4ｇ）にこの試験品
を0.5ｇ塗布し、調合香料のみである対照品は0.35ｇ塗
布した。次いで、温度２５℃、湿度５０％の恆温、恆湿
の部屋内で、調香技術者５名からなる判定者により、塗
布終了直後（０分）より６０分、１８０分、２４０分、
４２０分後迄の香りの変化の度合を下記第４表の判定基
準に従って判定し、その結果を◎、○、△、×で示し
た。 (3) Reservation effect test Model compounded fragrance consisting of 10 kinds of fragrance substances shown in Table 3 7
A test product was prepared by uniformly dissolving and mixing 0 wt% and 30 wt% of the sample, 0.5 g of this test product was applied to odor paper (9 cm x 9 cm 2.4 g), and 0.35 g of the control product containing only the fragrance was applied. . Next, in a room at a temperature of 25 ° C. and a humidity of 50%, a judge consisting of 5 fragrance technicians, 60 minutes, 180 minutes, 240 minutes immediately after the end of application (0 minutes),
The degree of fragrance change up to 420 minutes was judged according to the judgment criteria shown in Table 4 below, and the results are shown by ⊚, ○, Δ, and ×.
合成例１ 水素化ナトリウム28.8ｇ（1.2ｍｏ）を乾燥ジメチル
フォルムアミド１に溶解した後、グルコース８６ｇ
（0.2ｍｏ）を徐々に加え３０分間攪拌する。次い
で、温度０℃に冷却して、予め用意したリナロールの臭
化物１３０ｇ（0.6ｍｏ）を加えた後、温度を１０℃
に設定し１日間攪拌反応せしめた。引続きメタノールで
余剰の未反応物を分解処理した。反応生成物をｎ−ヘキ
サンで抽出し、減圧下でｎ−ヘキサンを留出除去して濃
縮物を得た。この濃縮物をシリカゲルカラムクロマトグ
ラフィーにより、クロロフォルム−メタノール混合液を
用いて精製して無色、無臭、透明液体である目的のエー
テル化合物〔モノ−Ｏ−（リナリル）−グルコピラノー
ス、ジ−Ｏ−（リナリル）−グルコピラノース、トリ−
Ｏ−（リナリル）−グルコピラノース、テトラ−Ｏ−
（リナリル）−グルコピラノース、ペンタ−Ｏ−（リナ
リル）−グルコピラノース〕１９ｇを得た。 Synthesis Example 1 Sodium hydride (28.8 g, 1.2 mo) was dissolved in dry dimethylformamide 1, and glucose was added (86 g).
(0.2mo) is gradually added and stirred for 30 minutes. Then, after cooling to a temperature of 0 ° C. and adding 130 g (0.6 mo) of linalool bromide prepared in advance, the temperature was raised to 10 ° C.
The reaction was stirred for 1 day. Subsequently, the excess unreacted material was decomposed with methanol. The reaction product was extracted with n-hexane, and n-hexane was distilled off under reduced pressure to obtain a concentrate. The concentrate was purified by silica gel column chromatography using a chloroform-methanol mixture to obtain an objective ether compound as a colorless, odorless, transparent liquid [mono-O- (linalyl) -glucopyranose, di-O- ( Linalyl) -glucopyranose, tri-
O- (linalyl) -glucopyranose, tetra-O-
19 g of (linalyl) -glucopyranose, penta-O- (linalyl) -glucopyranose] was obtained.
このものを後記実施例の試料に供した。This was used as the sample of the below-mentioned example.
ＩＲ(neat、cm-1) ３８００〜３２００、 ３０５０〜２９２０、 １２００〜１０００、 合成例２ 合成例１と同様にして、グルコースをガラクトース３６
ｇ（0.2ｍｏ）に、リナロールの臭化物をシス−３−
ヘキサノールの臭化物９８ｇ（0.6ｍｏ）に替えて反
応させ、無色、無臭、透明液体の目的のエーテル化合物
〔モノ−Ｏ−（シス−３−ヘキセニル）−ガラクトピラ
ノース、ジ−Ｏ−（シス−３−ヘキセニル）−ガラクト
ピラノース、トリ−Ｏ−（シス−３−ヘキセニル）−ガ
ラクトピラノース、テトラ−Ｏ−（シス−３−ヘキセニ
ル）−ガラクトピラノース、ペンタ−Ｏ−（シス−３−
ヘキセニル）−ガラクトピラノース〕１８ｇを得た。IR (neat, cm −1 ) 3800 to 3200, 3050 to 2920, 1200 to 1000, Synthesis Example 2 Glucose was replaced with galactose 36 in the same manner as in Synthesis Example 1.
g (0.2mo), add linalool bromide to cis-3-
The target ether compound [mono-O- (cis-3-hexenyl) -galactopyranose, di-O- (cis-3-) was obtained as a colorless, odorless, transparent liquid by reacting with 98 g (0.6 mo) of hexanol bromide. Hexenyl) -galactopyranose, tri-O- (cis-3-hexenyl) -galactopyranose, tetra-O- (cis-3-hexenyl) -galactopyranose, penta-O- (cis-3-).
18 g of (hexenyl) -galactopyranose] was obtained.
ＩＲ(neat、cm-1) ３８００〜３２００、 ３０３０〜２９１０、 １２００〜１０００、 合成例３ 合成例１と同様にして、グルコース３６ｇ（0.2ｍｏ
）とシトロネルロールの臭化物１３１ｇ（0.6ｍｏ
）との反応により無色、無臭、透明液体の目的のエー
テル化合物〔モノ−Ｏ−（シトロネリル）−グルコピラ
ノース、ジ−Ｏ−（シトロネリル）−グルコピラノー
ス、トリ−Ｏ−（シトロネリル）−グルコピラノース、
テトラ−Ｏ−（シトロネリル）−グルコピラノース、ペ
ンタ−Ｏ−（シトロネリル）−グルコピラノース〕１５
ｇを得た。IR (neat, cm −1 ) 3800 to 3200, 3030 to 2910, 1200 to 1000, Synthesis Example 3 In the same manner as in Synthesis Example 1, glucose 36 g (0.2mo
) And 131 g of citronellol bromide (0.6 mo
) Colorless, odorless, and transparent liquid target ether compound [mono-O- (citronellyl) -glucopyranose, di-O- (citronellyl) -glucopyranose, tri-O- (citronellyl) -glucopyranose,
Tetra-O- (citronellyl) -glucopyranose, penta-O- (citronellyl) -glucopyranose] 15
g was obtained.
ＩＲ(neat、cm-1) ３８００〜３２００、 ３０４０〜２８８０、 １２００〜１０００、 合成例４ 合成例１と同様にして、キシロース３０ｇ（0.2ｍｏ
）とメントールの臭化物１３１ｇ（0.6ｍｏ）との
反応により、無色、無臭、透明液体の目的のエーテル化
合物〔モノ−Ｏ−（メンチル）−キシロピラノース、ジ
−Ｏ−（メンチル）−キシロピラノース、トリ−Ｏ−
（メンチル）−キシロピラノース、テトラ−Ｏ−（メン
チル）−キシロピラノース〕１４ｇを得た。IR (neat, cm −1 ) 3800 to 3200, 3040 to 2880, 1200 to 1000, Synthetic Example 4 In the same manner as in Synthetic Example 1, 30 g of xylose (0.2 mo)
) With 131 g (0.6 mo) of menthol bromide, the target ether compound [mono-O- (menthyl) -xylopyranose, di-O- (menthyl) -xylopyranose, tri -O-
14 g of (menthyl) -xylopyranose and tetra-O- (menthyl) -xylopyranose] were obtained.
ＩＲ(neat、cm-1) ３８００〜３２００、 ３０００〜２８５０、１４５０ １２００〜１０００、 実施例１〜６、比較例１〜４ 合成例１〜４で得られた本発明の香料用保留剤であるエ
ーテル化合物及びこれらの混合物を試料として、前記安
定性試験及びヒト皮膚貼布試験を実施し、更に、比較例
１のベンジルベンゾエート、比較例２のジエチレングリ
コールモノエチルエーテル、ジベンザルソルビット、Ｄ
−ベンジリデンソルビトールの試料と共に保留効果試験
を実施した。その結果を第５表に記載する。IR (neat, cm −1 ) 3800 to 3200, 3000 to 2850, 1450 1200 to 1000, Examples 1 to 6, Comparative Examples 1 to 4 It is a perfume retention agent of the present invention obtained in Synthesis Examples 1 to 4. The stability test and the human skin patch test were carried out using ether compounds and mixtures thereof as samples, and further, benzyl benzoate of Comparative Example 1, diethylene glycol monoethyl ether of Comparative Example 2, dibenzal sorbit, D
-A retention effect test was performed with a sample of benzylidene sorbitol. The results are shown in Table 5.
第５表に示す如く、本発明の香料用保留剤である合成例
１〜４のエーテル化合物を試料とした実施例１〜６は化
学的に安定で、皮膚刺激も無く、更には比較例１〜４の
試料と比較して明らかに香料の保留効果に優れている。 As shown in Table 5, Examples 1 to 6 using the ether compounds of Synthetic Examples 1 to 4 as the fragrance-retaining agent of the present invention as samples were chemically stable, did not cause skin irritation, and further Comparative Example 1 The retention effect of the fragrance is obviously superior to the samples of Nos. 4 to 4.
（発明の効果） 以上の如く、本発明の前記エーテル化合物類は無色、無
臭の液体であり、化学的に安定であると共に皮膚安全性
に優れ、香料に有効成分として含有し、保留剤としての
効果を発現することが認められた(Effects of the Invention) As described above, the ether compounds of the present invention are colorless and odorless liquids, are chemically stable and have excellent skin safety, and are contained as an active ingredient in a fragrance and used as a holding agent. It was recognized that the effect was expressed
Claims (1)
炭化水素基を示し（ｘ＋ｚ＝１２、ｙ＋ｚ＝６、ｚ＝１
〜５で、Ｒが芳香環の場合を除く。）で表されるエーテ
ル化合物の少なくとも一つを有効成分として香料に配合
し、その配合量が５〜７０重量％であることを特徴とす
る香料用保留剤。1. C 6 H x O y- (OR) z (wherein C 6 H x O y is a cyclic 6-carbon sugar residue, R is a hydrocarbon group having 4 to 20 carbon atoms (x + z = 12, y + z = 6, z = 1
Except when R is an aromatic ring. ) At least one ether compound represented by the formula (1) is added to a fragrance as an active ingredient, and the content of the fragrance is 5 to 70% by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20434784A JPH0631398B2 (en) | 1984-09-28 | 1984-09-28 | Reserving agent for fragrance |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20434784A JPH0631398B2 (en) | 1984-09-28 | 1984-09-28 | Reserving agent for fragrance |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6183114A JPS6183114A (en) | 1986-04-26 |
| JPH0631398B2 true JPH0631398B2 (en) | 1994-04-27 |
Family
ID=16488993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20434784A Expired - Lifetime JPH0631398B2 (en) | 1984-09-28 | 1984-09-28 | Reserving agent for fragrance |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0631398B2 (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5728371A (en) * | 1996-04-29 | 1998-03-17 | L'oreal, S.A. | Skin protection, fragrance enhancing and vitamin delivery composition |
| DE19640986A1 (en) * | 1996-10-04 | 1998-04-16 | Henkel Kgaa | Fixation of fragrances from detergents and cleaning agents on hard and soft surfaces |
| RU2660416C2 (en) * | 2013-07-03 | 2018-07-06 | Басф Се | Mixtures of compounds, preparation and use thereof |
| CN107810259A (en) | 2015-06-12 | 2018-03-16 | 宝洁公司 | Perfume composition |
| EP3103431A1 (en) | 2015-06-12 | 2016-12-14 | The Procter and Gamble Company | Fragrance compositions and uses thereof |
| EP3103523B1 (en) | 2015-06-12 | 2025-10-29 | The Procter & Gamble Company | Absorbent article comprising fragrance composition |
| EP3743163B1 (en) | 2018-02-07 | 2026-04-01 | Coty, Inc. | Fragrance compositions and uses thereof |
| WO2021247838A1 (en) | 2020-06-05 | 2021-12-09 | Coty Inc. | Fragrance composition comprising a fragrance component and a non-odorous fragrance modulator |
| WO2023055916A1 (en) | 2021-09-30 | 2023-04-06 | Coty Inc. | Fragrance compositions based on polyurethane |
| CN118201587A (en) | 2021-11-04 | 2024-06-14 | 科蒂公司 | Alcohol-free fragrance base |
| FR3143998A1 (en) | 2022-12-21 | 2024-06-28 | Coty Inc. | PERFUME COMPOSITIONS AND THEIR USES |
| NL2034750B1 (en) | 2023-05-02 | 2024-11-14 | Coty Inc | Ethanol-free fragrance chassis |
| EP4704795A2 (en) | 2023-05-05 | 2026-03-11 | Coty Inc. | Fragrance compositions |
-
1984
- 1984-09-28 JP JP20434784A patent/JPH0631398B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6183114A (en) | 1986-04-26 |
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