CN105283435B - 有机化合物中或与之相关的改进 - Google Patents
有机化合物中或与之相关的改进 Download PDFInfo
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- CN105283435B CN105283435B CN201480032831.5A CN201480032831A CN105283435B CN 105283435 B CN105283435 B CN 105283435B CN 201480032831 A CN201480032831 A CN 201480032831A CN 105283435 B CN105283435 B CN 105283435B
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- Prior art keywords
- perfume
- compound
- mixture
- hydroxy
- composition
- Prior art date
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- 150000002894 organic compounds Chemical class 0.000 title description 2
- BKYXRISZNNAYRG-UHFFFAOYSA-N 9-hydroxy-5,9-dimethyldec-1-en-4-one Chemical compound CC(C(CC=C)=O)CCCC(C)(O)C BKYXRISZNNAYRG-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000000203 mixture Substances 0.000 claims description 164
- 239000002304 perfume Substances 0.000 claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 66
- 239000004615 ingredient Substances 0.000 claims description 41
- 239000011541 reaction mixture Substances 0.000 claims description 28
- -1 hydroxyaryl alcohol Chemical compound 0.000 claims description 26
- 239000003205 fragrance Substances 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 23
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 23
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 17
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 12
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 10
- 239000003963 antioxidant agent Substances 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 230000003078 antioxidant effect Effects 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229940125898 compound 5 Drugs 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- ZHOOOLQOWQVYOE-UHFFFAOYSA-N 2-cyclohexylidene-2-phenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)=C1CCCCC1 ZHOOOLQOWQVYOE-UHFFFAOYSA-N 0.000 claims description 5
- YVSNOTITPICPTB-UHFFFAOYSA-N 4-methyl-2-(2-methylpropyl)oxan-4-ol Chemical compound CC(C)CC1CC(C)(O)CCO1 YVSNOTITPICPTB-UHFFFAOYSA-N 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- WFEISWUNAJPLRX-UHFFFAOYSA-N 30168-23-1 Chemical compound C12CCCC2C2CC(=CCCC=O)C1C2 WFEISWUNAJPLRX-UHFFFAOYSA-N 0.000 claims description 3
- GLASPHLTTAHWPI-UHFFFAOYSA-N methyl 2-(2-hexyl-3-oxocyclopentyl)acetate Chemical compound CCCCCCC1C(CC(=O)OC)CCC1=O GLASPHLTTAHWPI-UHFFFAOYSA-N 0.000 claims description 3
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 claims description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 3
- 239000000047 product Substances 0.000 description 53
- 235000019645 odor Nutrition 0.000 description 29
- 238000009472 formulation Methods 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- 238000004140 cleaning Methods 0.000 description 11
- 238000004821 distillation Methods 0.000 description 11
- 239000002243 precursor Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000002671 adjuvant Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000003599 detergent Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 9
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000001241 acetals Chemical class 0.000 description 7
- 239000002537 cosmetic Substances 0.000 description 7
- LCRYKIFRBLQIAW-UHFFFAOYSA-N 3,7-dimethylocta-1,6-diene-1,3-diol Chemical compound CC(C)=CCCC(C)(O)C=CO LCRYKIFRBLQIAW-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 150000004808 allyl alcohols Chemical class 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000002979 fabric softener Substances 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- YWTIDNZYLFTNQQ-UHFFFAOYSA-N Dehydrolinalool Chemical compound CC(C)=CCCC(C)(O)C#C YWTIDNZYLFTNQQ-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000002386 air freshener Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000002453 shampoo Substances 0.000 description 5
- 239000007787 solid 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
- SRPFYGUVQUDURC-UHFFFAOYSA-N 2,6-Dimethyl-7-octene-2,6-diol Chemical compound CC(C)(O)CCCC(C)(O)C=C SRPFYGUVQUDURC-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 244000068485 Convallaria majalis Species 0.000 description 4
- 235000009046 Convallaria majalis Nutrition 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 241000220317 Rosa Species 0.000 description 4
- 229940022663 acetate Drugs 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 229930007744 linalool Natural products 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000006462 rearrangement reaction Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 244000089742 Citrus aurantifolia Species 0.000 description 3
- 238000005821 Claisen rearrangement reaction Methods 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000645 desinfectant Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 3
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 3
- 238000005498 polishing Methods 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
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- YHRUHBBTQZKMEX-YFVJMOTDSA-N (2-trans,6-trans)-farnesal Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\C=O YHRUHBBTQZKMEX-YFVJMOTDSA-N 0.000 description 2
- NPFVOOAXDOBMCE-PLNGDYQASA-N (3Z)-hex-3-en-1-yl acetate Chemical compound CC\C=C/CCOC(C)=O NPFVOOAXDOBMCE-PLNGDYQASA-N 0.000 description 2
- GLZPCOQZEFWAFX-JXMROGBWSA-N (E)-Geraniol Chemical compound CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 2
- SSNZFFBDIMUILS-ZHACJKMWSA-N (E)-dodec-2-enal Chemical compound CCCCCCCCC\C=C\C=O SSNZFFBDIMUILS-ZHACJKMWSA-N 0.000 description 2
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- JJRIKWAHJMMDSF-UHFFFAOYSA-N 2,6-dimethyloct-7-yne-2,6-diol Chemical compound CC(C)(O)CCCC(C)(O)C#C JJRIKWAHJMMDSF-UHFFFAOYSA-N 0.000 description 2
- DNRJTBAOUJJKDY-UHFFFAOYSA-N 2-Acetyl-3,5,5,6,8,8-hexamethyl-5,6,7,8- tetrahydronaphthalene Chemical compound CC(=O)C1=C(C)C=C2C(C)(C)C(C)CC(C)(C)C2=C1 DNRJTBAOUJJKDY-UHFFFAOYSA-N 0.000 description 2
- HMKKIXGYKWDQSV-SDNWHVSQSA-N 2-Pentyl-3-phenyl-2-propenal Chemical compound CCCCC\C(C=O)=C/C1=CC=CC=C1 HMKKIXGYKWDQSV-SDNWHVSQSA-N 0.000 description 2
- PANBRUWVURLWGY-UHFFFAOYSA-N 2-undecenal Chemical compound CCCCCCCCC=CC=O PANBRUWVURLWGY-UHFFFAOYSA-N 0.000 description 2
- ZGIGZINMAOQWLX-NCZFFCEISA-N 3,7,11-Trimethyl-2,6,10-dodecatrienyl acetate Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\COC(C)=O ZGIGZINMAOQWLX-NCZFFCEISA-N 0.000 description 2
- JTVKFAPEIBMMHX-UHFFFAOYSA-N 3-(4-methylcyclohex-3-en-1-yl)butan-1-ol Chemical compound OCCC(C)C1CCC(C)=CC1 JTVKFAPEIBMMHX-UHFFFAOYSA-N 0.000 description 2
- XOJDKWNFMFCXNE-UHFFFAOYSA-N 8,8-Diethoxy-2,6-dimethyl-2-octanol Chemical compound CCOC(OCC)CC(C)CCCC(C)(C)O XOJDKWNFMFCXNE-UHFFFAOYSA-N 0.000 description 2
- QCJVKUULZGKQDG-UHFFFAOYSA-N 8,8-Dimethoxy-2,6-dimethyl-2-octanol Chemical compound COC(OC)CC(C)CCCC(C)(C)O QCJVKUULZGKQDG-UHFFFAOYSA-N 0.000 description 2
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- 239000000853 adhesive Substances 0.000 description 2
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- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 2
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- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 2
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- 239000004317 sodium nitrate Substances 0.000 description 1
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- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- 229940116411 terpineol Drugs 0.000 description 1
- 230000008542 thermal sensitivity Effects 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
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- 230000001256 tonic effect Effects 0.000 description 1
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- 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
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- 210000002700 urine Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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- 229960000834 vinyl ether Drugs 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
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Abstract
式(I)的5,9‑二甲基‑9‑羟基‑癸烯‑4‑醛。
Description
本发明涉及新化合物、制备所述化合物的方法及其作为香料成分的用途,尤其是其作为香料成分赋予香料组合物铃兰气味特征的用途。本发明还涉及通过所述化合物加香的香料组合物和制品如精细香料或消费品组合物,或者含有所述化合物的香料组合物。
具有铃兰(或山谷百合)气味特征的化合物作为香料成分是非常寻求的。这些化合物是花香基质中的重要成分并且可以作为协调剂通过生成许多类型的香料中起作用。这种类型的化合物广泛用于个人护理和消费者护理产品以及精细香料,以便生成令人愉快的气味或掩蔽令人不愉快的气味。
因其铃兰气味香型而具有广泛价值的极佳的香料成分是4(4-羟基-4-甲基戊基)3-环己烯甲醛,另外其已知为环己醛(cyclohexal)(LyralTM)。该化合物已经广泛应用于精细香料以及个人和家庭护理产品。然而,根据消费者安全科学委员会(EuropeanScientific Committee for Consumer Safety)(SCCS)的发现,其具有过敏的问题并且目前其可能会在欧盟受到管制。
本发明所要解决的问题是提供新的成分和新的香料制剂,特别地,它们被调香师注意并认为与环己醛具有基本上相同的气味特征以及具有与环己醛相比类似或甚至改善的香料性能。
因此,在第一个方面,本发明提供式(I)的化合物5,9-二甲基-9-羟基-癸烯-4-醛
申请人发现本发明化合物具有令人想起环己醛的经典花香、青香、铃兰气味香型。因此,5,9-二甲基-9-羟基-癸烯-4-醛能够作为环己醛的极其适合的替代品。
GB981,702公开了一种制备γ,δ-不饱和醛和酮的方法。该专利概括性地描述了烯丙醇与烯醇醚的反应以及随后在高温下的重排反应。在试图证明合成方法的范围的努力中,提供了使用各种带有不同官能团的烯丙醇的实例。所述实例包括带有饱和和不饱和烷基、环烷烃、双键、芳族环以及含氧官能团例如羟基的烯丙醇。
在GB981,702的实施例27中,其意图描述从羟基-取代的烯丙醇底物羟基芳樟醇起始制备化合物5,9-二甲基-9-羟基-癸烯-4-醛的方法。
反应通过在磷酸中混合羟基芳樟醇和乙烯基乙基醚来进行。将该有机混合物在碱性下进行后处理并蒸馏,之后将馏出物加入到亚硫酸氢钠水溶液中并将有机层弃去。然后将水相用30%氢氧化钠处理,之后用乙醚萃取。将水相弃去并将醚层用碳酸氢盐处理。将乙醚蒸发后,蒸馏粗产物以分离终产物。将终产物通过其气味特征以及其沸点和折射率来表征。
分离的终产物被描述为具有“令人愉快的果香和烟熏-油脂气味”。这一发现,当考虑到申请人自己的发现即目标化合物5,9-二甲基-9-羟基-癸烯-4-醛实际上显示了与GB981,702中所报告的气味完全不相关的经典铃兰气味时,是难以理解的。此外,如申请人所测量的,化合物5,9-二甲基-9-羟基-癸烯-4-醛的沸点和折射率测量值显著不同于根据所述实施例27的方法获得的产物。具体来说,实施例27中获得的产物具有所报告的83-85℃/0.03mm的沸点和nD 201.4698的折射率。事实上,申请人发现的5,9-二甲基-9-羟基-癸烯-4-醛的真实值是106-109℃/0.05mm和nD 201.4659。
当申请人重复实施例27中所描述的合成条件时,未能回收任何5,9-二甲基-9-羟基-癸烯-4-醛。事实上,在将大量聚合残留物除去之后所回收的是化合物的异构体混合物:
通过分析,未发现该化合物具有85℃/0.03mm的沸点和1.4682的nD 20。此外,由调香师所描述的气味特征为果香、柑橘香、油脂味、微热铁味(slightly hot iron)和金属味。明显地,这些参数与GB981,702的实施例27分离的终产物所公开的那些显示出显著的一致性。
从前述相当明显的是GB981,702就化合物5,9-二甲基-9-羟基-癸烯-4-醛或其制备而言没有构成充分公开。事实上,GB981,702的作者没有认识到的、而是申请人在对该反应投入大量研究努力之后发现的是烯丙醇原料(如在实施例27中的羟基芳樟醇的情形,其是使用羟基-取代的烯丙醇原料的唯一实施例)中羟基取代基的引入极大地改变了产物的稳定性和化学性质。使用亚硫酸盐加合物作为从复杂混合物中分离醛的方式是GB981,702作者使用的已知技术,然而从加合物释放终产物是通过在强碱(30%氢氧化钠)中水解以及随后用强酸的处理而实现的,而这引起了非所需的副反应。
申请人令人惊讶地发现5,9-二甲基-9-羟基-癸烯-4-醛既是热不稳定的,又是在碱性介质中不稳定的,因此,如果想要成功制备,需要温和的反应和分离条件。
因此,在另一方面,本发明提供从反应混合物制备5,9-二甲基-9-羟基-癸烯-4-醛(I)的方法,所述方法包括以基本上不含任何酸或碱的形式提供反应混合物,并从所述反应混合物蒸馏混合物5,9-二甲基-9-羟基-癸烯-4-醛。
在本发明的特定实施方案中,如果用含水洗涤液中和的话,可以以基本上不含任何酸或碱的形式提供反应混合物,所述含水洗涤液可以是任选地含有盐如氯化钠的水、酸的水溶液或碱的水溶液中的一种或多种。
酸可以选自C1-C4羧酸如乙酸,多羧酸如柠檬酸,和弱无机酸。
碱可以选自弱碱,如碳酸(氢)钠或钾。
当洗涤之后洗涤液具有约6.5至约7.5的pH时,认为反应混合物基本上不含酸或碱。
申请人发现在高于pH10的碱性条件下,或在低于约pH4的酸性条件下,5,9-二甲基-9-羟基-癸烯-4-醛在环境温度下快速降解,并且降解在高温下甚至进行得更快。因此,如果要实现制备和分离5,9-二甲基-9-羟基-癸烯-4-醛的目标,则不能经历碱性条件,或者如果遇到碱性条件,则其不能高于10,更具体地不能高于9.5,并且甚至更具体地不能高于9。应该避免强碱如氢氧化钠,优选地,即使使用,应该小心pH不能升高至前述数值。并且进一步地,当蒸馏5,9-二甲基-9-羟基-癸烯-4-醛以便以嗅觉纯形式提供它时,应该首先确保含有它的反应混合物如前所述的基本上不含酸或碱。
蒸馏可以在95℃-200℃的温度和0.01mm-10mm、更具体地0.01mm-5mm的压力下进行。
由于5,9-二甲基-9-羟基-癸烯-4-醛的热敏感性,尽可能地缩短蒸馏步骤的持续时间可能是所需的。为了简化蒸馏过程并缩短持续时间,通过用焦亚硫酸钠水溶液处理5,9-二甲基-9-羟基-癸烯-4-醛以形成溶于水相的5,9-二甲基-9-羟基-癸烯-4-醛的磺酸盐,可以首先从反应混合物的有机副产物分离5,9-二甲基-9-羟基-癸烯-4-醛。下式的磺酸盐形成了本发明的另一方面。
之后,可以将有机溶剂添加到水相中,并且5,9-二甲基-9-羟基-癸烯-4-醛可以通过用弱碱例如碳酸钠的稀溶液处理磺酸盐而再生。一旦再生,5,9-二甲基-9-羟基-癸烯-4-醛分配到有机相中,并且用稀的弱酸洗涤该相以除去痕量的碱,之后进行蒸馏。
5,9-二甲基-9-羟基-癸烯-4-醛可以从烯丙醇前体制备。这一前体可以是芳樟醇或羟基-取代的烯丙醇如羟基芳樟醇。更进一步地,其可以是羟基-取代的烯丙醇,其中非-烯丙基羟基取代基为保护或掩蔽形式,如其乙酸酯。
通过在酸存在下进行克莱森重排反应使烯丙醇前体转化为5,9-二甲基-9-羟基-癸烯-4-醛,所述克莱森重排反应为本领域技术人员众所周知的技术。使用酸以首先在烯丙醇羟基基团上进行反式-醚化,而且如本领域中众所周知的是所形成的醚进行重排反应。
烯丙醇前体具有下式:
其中,
在本发明的优选实施方案中,所述前体是羟基芳樟醇,然而,也可以使用羟基芳樟醇的保护形式,例如乙酸酯。
如果所述前体包含基团作为双键,则一旦进行克莱森重排,根据本领域技术人员已知的技术,该双键可以被水解以添加羟基并释放所需的5,9-二甲基-9-羟基-癸烯-4-醛。因此,采取步骤以确保如上所述的反应混合物在进行蒸馏之前基本上不包含酸或碱。
烯丙醇前体是商购的或者可以使用本领域技术人员已知的技术从常用的原料制备。
当使乙烯基醚与烯丙醇前体反应时,在酸或金属催化剂存在下在环境温度至约200℃的温度下,克莱森重排反应容易进行。典型地,该反应在高压下在高压釜中进行。在高压釜中可以使用任何所需的高于大气压的压力,例如高至100巴,并且更具体地约5-20巴。
然而,申请人已经发现,当使用二甘醇二乙烯基醚或三甘醇二乙烯基醚作为乙烯基醚时,所述反应可以在大气压力下在未加压的反应容器中进行。
任选地,反应在惰性气氛例如氮气氛下进行。
一旦重排反应完全,可以用酸处理反应混合物以水解任何在反应进行过程中形成的缩醛。
在一个特定实施方案中,本发明提供制备5,9-二甲基-9-羟基-癸烯-4-醛(I)的方法,所述方法包括使烯丙醇前体、优选羟基芳樟醇与二甘醇二乙烯基醚在酸存在下在惰性气氛下在大气压下和125-200℃的温度下反应;用稀酸处理包含5,9-二甲基-9-羟基-癸烯-4-醛的反应混合物以基本上水解所有缩醛;并基本上除去所有酸和碱,之后使中和的反应混合物以如上所述的方式进行蒸馏。
在另一方面,本发明提供制备5,9-二甲基-9-羟基-癸烯-4-醛(I)的方法,所述方法包括以下步骤:
I)使羟基芳樟醇(3)与乙基乙烯基醚在酸中在惰性气氛下在1-100巴、更具体5-20巴和(-)10至200℃、更具体地140-190℃的温度下反应,形成包含缩醛的反应混合物;
II)在(-)20至40℃和大气压下酸化冷却的反应混合物以水解所述缩醛;
III)在碱中中和反应混合物,之后调节反应混合物的pH至略微酸性pH4-6,得到5,9-二甲基-9-羟基-癸烯-4-醛(I);并且
IV)蒸馏反应混合物,以分离纯5,9-二甲基-9-羟基-癸烯-4-醛(I)。
如上所述的重排反应,例如如上所述的羟基芳樟醇(3)与乙基乙烯基醚的反应在酸性条件下进行。用于本发明的具体的酸包括苯基膦酸、磺基水杨酸、用各种用量的胺缓冲的磷酸、磷酸、铵盐、烷基羧酸和芳基羧酸。
尽管羟基芳樟醇(3)是常用的原料,其也可以以直接的方式由3,7-二甲基辛-6-烯-1-炔-3-醇(1)起始并使该化合物在硫酸水溶液中水合以得到化合物(2)而制备。用适合的催化剂如钯催化剂选择性氢化三键得到芳樟醇(3),其可以按照本发明的制备方法进一步转化为目标化合物5,9-二甲基-9-羟基-癸烯-4-醛(I)。概括性反应方案如方案1中所示:
方案1
就其E-或Z-异构体而言,可以以纯或富含形式提供5,9-二甲基-9-羟基-癸烯-4-醛(I)。这一增香剂的强度(即检测阈值)以及嗅觉特征或质量可能被包含在异构体混合物中的几何异构体的相对比例所影响。如果纯形式的异构体是所需的,可以使用通常在本领域中已知的合成方法或通过物理分离来得到它们。
在本发明一个特定实施方案中,5,9-二甲基-9-羟基-癸烯-4-醛(I)的E/Z比是在8:2至2:8的范围之内,或者更具体地为6:4的比例。
在本发明一个特定实施方案中,当50-70wt%的5,9-二甲基-9-羟基-癸烯-4-醛以E-形式存在且30-50wt%为Z-形式时,得到特别希望的嗅觉印象。
可以纯化式(I)的化合物以得到其嗅觉纯形式,也就是说,其中没有痕量杂质以能够显著影响气味特征或质量的水平存在的形式。然而申请人已经发现,来自从其中分离5,9-二甲基-9-羟基-癸烯-4-醛的反应混合物的一些副产物能够补充气味质量,或者至少未不利地影响气味质量。
因此,在本发明的另一个方面,提供香料混合物,其包含5,9-二甲基-9-羟基-癸烯-4-醛(I)和式(II)的化合物
在本发明一个特定实施方案中,提供香料混合物,其包含5,9-二甲基-9-羟基-癸烯-4-醛(I)和式(II)的化合物,其比例(重量/重量)为95:5份;更具体地99:1份,更具体地99.1:0.9份;99.2:0.8份;99.3:0.7份;99.4:0.6份;99.5:0.5份;99.6:0.4份;99.7:0.3份;99.8:0.2份;99.9:0.1份;99.95:0.05份;或者99.99:0.01份。本领域技术人员将会理解式(II)的化合物可以以纯形式存在或者可以作为异构体混合物存在。前述比例涉及异构体纯形式的化合物(II)或其任意异构体混合物。
发现上述式(I)的化合物和香料混合物显示出类似于环己醛的气味特征,并因此可以用于香料组合物中作为环己醛的替代品。
因此,在另外一个方面,本发明提供单独或者与化合物(II)混合的式(I)的化合物作为环己醛替代品的用途。
在仍然另外一个方面,本发明提供香料组合物,其包含单独或者与式(II)的化合物混合的式(I)的化合物,并且其不含环己醛。
在仍然另外一个方面,本发明提供加香制品如精细香料或个人或家庭护理产品,其被任选地与式(II)的化合物混合的式(I)的化合物加香。
尽管上述式(I)的化合物或其混合物具有非常类似于环己醛的气味特征,然而调香师可能会发现需要使用额外的与式(I)的化合物或香料混合物组合的香料成分以平衡或微调气味特征,例如,使上述化合物或混合物与环己醛的气味特征更为一致。
因此,在另外一个方面,本发明提供香料组合物,其包含任选地与上述式(II)的化合物混合的式(I)的化合物以及一种或多种以下成分:2-亚环己基-2-苯基乙腈,例如PEONILETM;4-(八氢-4,7-亚甲基-5H-茚-5-亚基)丁醛,例如DUPICALTM;和4-甲基-2-(2-甲基丙基)四氢-2H-吡喃-4-醇,例如FLOROSATM;2-(2-己基-3-氧代环戊基)乙酸甲酯,例如二氢茉莉酮酸甲酯TM。
在本发明一个特定实施方案中,香料组合物包含2-亚环己基-2-苯基乙腈。
在本发明另外一个特定实施方案中,香料组合物包含2-亚环己基-2-苯基乙腈和4-甲基-2-(2-甲基丙基)四氢-2H-吡喃-4-醇。
在本发明仍然另外一个特定实施方案中,香料组合物包含2-亚环己基-2-苯基乙腈和4-甲基-2-(2-甲基丙基)四氢-2H-吡喃-4-醇和4-(八氢-4,7-亚甲基-5H-茚-5-亚基)丁醛。
在本发明的香料组合物中,2-亚环己基-2-苯基乙腈,例如PEONILETM,可以以0.001-10重量份/1重量份5,9-二甲基-9-羟基-癸烯-4-醛使用。
在本发明的香料组合物中,4-甲基-2-(2-甲基丙基)四氢-2H-吡喃-4-醇,例如FLOROSATM,可以以0.01-20重量份/1重量份5,9-二甲基-9-羟基-癸烯-4-醛使用。
在本发明的香料组合物中,4-(八氢-4,7-亚甲基-5H-茚-5-亚基)丁醛,例如DUPICALTM,可以以0.0001-0.5重量份/1重量份5,9-二甲基-9-羟基-癸烯-4-醛使用。
在本发明的香料组合物中,2-(2-己基-3-氧代环戊基)乙酸甲酯,例如二氢茉莉酮酸甲酯TM,可以以0.001-10重量份/1重量份5,9-二甲基-9-羟基-癸烯-4-醛使用。
在香料组合物中,任选地与化合物(II)组合的式(I)的化合物可以以约1-30%重量、更具体地5-20%重量的量使用,基于所述香料组合物的总重量。
上述香料组合物显示出环己醛的气味特征,但是所述香料组合物不必仅限于这些成分。所述香料组合物可以包含一种或多种额外的香料成分。
可以与式(I)的化合物和谐地一起使用的特定的香料成分包括:
天然成分,如选自如来自鸢尾花,含羞草,依兰,香柠檬,茉莉和玫瑰的那些;
合成铃兰香料成分,如兔耳草醛(103-95-7),羟基香茅醛(107-75-5),羟基香茅醛二乙基缩醛(7779-94-4),铃兰醛(80-54-6),环己醛(31906-04-4),银醛(6658-48-6),波洁洪醛(18127-01-0),花青醛(125109-85-5),和环铃兰醛(7775-00-0);
玫瑰型调和花香成分,如乙基苯基醇(60-12-8),二甲基苯基乙基甲醇(103-05-9),香茅醇(106-22-9),玫瑰醇(106-22-9),Acet.DMBC(151-05-3),香叶醇(106-24-1),橙花醇(106-25-2),橙花叔醇(7212-44-4),玫瑰花醇(55066-48-3),邻甲基苯乙醇(19819-98-8),异丁酸香茅酯(97-89-2),和美研醇(103694-68-4);
小苍兰型调和花香成分,如芳樟醇(78-70-6),Ross i tol(215231-33-7),和花冠醇(83926-73-2);
丁香型调和花香成分,如Alc.肉桂醇(104-54-1),丙基苯基醇(122-97-4)和松油醇(8000-41-7);
茉莉型调和花香成分,如乙酸苄基酯(140-11-4),二氢茉莉酮酸甲酯(24851-98-7),己基肉桂醛(101-86-0),和戊基肉桂醛(122-40-7);
铃兰型调和花香成分,如超级铃兰(26330-65-4),羟基香茅醛二甲基缩醛(141-92-4),木兰醇(92046-49-6),新铃兰醇(Mugetanol)(63767-86-2),Mugesia(56836-93-2),吲哚(120-72-9)和吲哚烯液(67860-00-8);
青香调和成分,如顺式3-己烯醇(928-96-1),苯基乙醛(122-78-1),马赛醛(67845-30-1),乙酸顺式3-己烯醇酯(3681-71-8),缩醛CD(29895-73-6),Precarone(74499-58-4),梅弗兰醛(55066-49-4),爱林太尔(40910-49-4),格力克力二噁茂烷(68901-32-6),和花冠醇(83926-73-2);
清鲜调和成分,如C11十一碳烯醛(112-45-8),C11十一醛(112-44-7),C10醛(112-31-2),C12MNA醛(110-41-8),新洋茉莉醛(1205-17-0),柠檬醛(5392-40-5),Oxyde deLimette(73018-51-6),花青醛(125109-85-5),清风醛(67634-15-5),二氢金合欢醛(51513-58-7),二氢金合欢醇(51411-24-6),阿道克醛(141-13-9),香茅基氧基乙醛(7492-67-3),超级铃兰醛(71077-31-1)和十二烯醛(4826-62-4);
调和木香成分,如紫罗兰酮(8013-90-9)和甲基紫罗兰酮(1335-46-2);
调和粉香成分,如吐纳麝香(21145-77-7),西藏麝香(106-02-5),洋茉莉醛(120-57-0),和香兰素(121-33-5);和
不同的调和花香成分,如Phixia(107-75-5),金合欢醛(19317-11-4),乙酸金合欢酯(29548-30-9),乙酸玫瑰酯(141-11-7),环亚甲基香茅醇(15760-18-6),五月铃兰醇(5502-75-0),乙酸柑青酯(72403-67-9),和Melonia(3613-30-7),其中在括号中提供分子的CAS号。
除了上述可以作为式(I)的化合物的气味特征特定补充而使用的香料成分之外,可以使用常用于香料的其它香料成分,例如“Perfume and Flavour Chemicals”,S.Arctander,Allured Publishing Corporation,1994,IL,USA中所述的任意那些成分,将该文献引入本文参考,包括精油、植物提取物、净油、树脂型物、得自天然产物的增香剂等。然而,优选香料组合物不含或者基本上不含环己醛。
此外,香料组合物可以包含常用于香料制品的佐剂。术语“佐剂”是指因非所述组合物的嗅觉性能或不具体涉及所述组合物的气味特征的原因而可以用于香料组合物的成分。例如,佐剂可以是作为加工香料成分或包含所述成分的组合物的助剂起作用的成分,或它可以改善香料成分或包含它的组合物的操作或储存。它还可以是提供另外的有益性例如赋予颜色或质地的成分。它还可以是给香料成分或包含它的混合物或组合物中包含的一种或多种成分赋予耐光性或化学稳定性的成分。可以用于包含香料成分的香料组合物的佐剂的性质和类型的详细描述可能无法穷尽,但是必须提及,所述成分是本领域技术人员众所周知的。佐剂的实例包括溶剂和助溶剂;表面活性剂和乳化剂;粘度和流变调节剂;增稠剂和胶凝剂;防腐材料;色素、染料和着色物质;增充剂、填充剂和补益剂;抵抗热和光的有害作用稳定剂、填充剂、酸化剂、缓冲剂和抗氧化剂。
在本发明一个特定实施方案中,如本文所述的包含任选地与式(II)的化合物组合的式(I)的化合物的组合物或包含它们的香料组合物含有抗氧化剂佐剂。所述抗氧化剂可以选自TT(BASF)、Q(BASF)、生育酚(包括其异构体,CAS 59-02-9;364-49-8;18920-62-2;121854-78-2)、2,6-二(1,1-二甲基乙基)-4-甲基苯酚(BHT,CAS 128-37-0)和相关的酚类、氢醌(CAS 121-31-9)。更具体地,可以优先使用在柠檬酸三乙酯(TEC)中的Tinogard Q作为5,9-二甲基-9-羟基-癸烯-4-醛的抗氧化剂。抗氧化剂可以在纯化合物5,9-二甲基-9-羟基-癸烯-4-醛中以0.5-3%的水平使用。
如上所述,一定水平的化合物(II)可以用于补充5,9-二甲基-9-羟基-癸烯-4-醛(I)的气味特征。然而,由于与嗅觉质量相关的原因,化合物(II)的水平不应该太高,并且优选不应该超过如上所述的水平。申请人发现,除非小心防止5,9-二甲基-9-羟基-癸烯-4-醛(I)的过度氧化,则可能生成非所需水平的化合物(II)。因此,抗氧化剂应该与5,9-二甲基-9-羟基-癸烯-4-醛(I)组合使用。
此外,如果期望,则可以用递送媒介物配制用于本发明的香料成分或佐剂的任意一种或多种,以便得到期望的效果。递送媒介物可以包括包囊材料。或者,递送媒介物可以是固体支持物形式,例如其上可以以化学或物理方式结合一种或多种香料成分的聚合物支持物材料。此外,可以将一种或多种香料成分或佐剂溶于或分散于基质材料,该基质材料用于控制所述成分从其中释放出的速率。在一个可选的实施方案中,可以使一种或多种成分或佐剂支持在多孔底物上,例如环糊精或沸石或其它无机材料。在另一个实施方案中,可以以前-香料的形式提供一种或多种香料成分,其在适合的环境中反应以便以受控方式释放香料成分。
考虑到上述方面,可以理解,香料混合物或香料组合物可以是至少部分是固体形式、凝胶形式、泡沫体形式和/或液体形式的香料。如果以固体形式存在,则它可以采用颗粒、粉末或片剂形式。
可以使用本文所描述的式(I)的化合物,香料混合物或香料组合物以添加气味特征到所有形式的制品中,如精细香料、个人护理和家庭护理组合物。
根据本发明的另一方面,提供将铃兰气味赋予组合物的方法,该方法包括向所述组合物中添加式(I)的化合物、包含所述化合物的香料混合物或香料组合物的步骤。
个人和家庭护理组合物包括、但不限于纺织品处理产品、熨衣助剂、擦布、洗衣房清洁剂、清洁产品特别是用于硬和/或软表面的清洁产品、家庭清洁剂、护理产品、洗涤护理产品、洗衣房护理产品、室内香料和空气清新剂、调理剂、着色剂、织物调理剂、调理底物、药物、作物保护产品、抛光剂、食品、化妆品、肥料、建筑材料、粘合剂、漂白剂、脱钙剂、汽车护理产品、地板护理产品、餐具护理产品、皮革护理产品或家具护理产品、洗刷物品、消毒剂、香料、霉菌去除剂和/或上述举出产品的前体。
本领域技术人员完全知晓香料成分,混合物和组合物对个人和家庭护理组合物的适用性,且这类组合物的极为详细的描述在本文中不再详举。然而,可以举出的具体组合物包括清洁组合物;汽车护理组合物;化妆品组合物;纺织品处理组合物;和空气清新剂和空气护理组合物。
清洁产品包括:
厕所清洁剂或盥洗室清洁剂,换句话说,是用于清洁盥洗室清洗盆和尿池的产品,这些产品优选以粉末、块、片剂或液体形式提供,优选凝胶。除其它典型的成分外,例如表面活性剂,它们一般还包括有机酸,例如柠檬酸和/或乳酸)或硫酸氢钠、酰氨基硫酸或磷酸,它们用于除去石灰垢或尿垢;
管道清洁产品或排水道清洁剂。这些典型地是强碱性产品,它们通常用于除去管道阻塞物,其包含有机材料-例如毛发、脂肪、食品残留物、肥皂沉积物等。添加Al粉或Zn粉可以用于形成具有泡腾效果的H2气体。可能的成分通常是碱洗涤剂、碱式盐、氧化剂和中性盐。粉末形式的提供形式优选还包括硝酸钠和氯化钠。液体形式的管道清洁产品可以优选还包括次氯酸盐。还存在基于酶的排水道清洁剂。酸性产品同样是可能的;
通用或万能或一般用途的清洁剂。它们是可以通用于家庭和商业中的所有硬表面的清洁剂,可以以湿或潮湿的形式擦掉。一般而言,它们是中性的或弱碱性的或弱酸性的产品,尤其是液体产品。万能或一般用途的清洁剂通常包含表面活性剂、增量剂、溶剂和助水溶物、染料、防腐剂等;
具有专用洗涤剂特性的万能清洁剂。它们还包括活性抗微生物成分(例如醛类、醇类、季铵化合物、两性表面活性剂、三氯生);
卫生清洁剂。这些是用于清洁浴室和厕所的产品。碱性卫生清洁剂优选用于除去脂肪污物,而酸性卫生清洁剂特别用于除去石灰垢。卫生清洁剂还有利地具有相当的消毒剂作用,特别是包含氯的强碱性卫生清洁剂;
可以以凝胶或泡沫喷雾剂形式提供的烤箱清洁剂或烤架清洁剂。它们一般用于除去烧烤或碳化的食物残留物。优选使用例如氢氧化钠、偏硅酸钠、2-氨基乙醇这样的强碱性制品得到烤箱清洁剂。此外,它们一般包含阴离子和/或非离子表面活性剂、水溶性溶剂,且在一些情况中,包含增稠剂,例如聚羧酸盐和羧甲基纤维素;
金属抛光剂。它们是用于具体类型的金属例如不锈钢或银的清洁剂。不锈钢清洁剂除包含酸(优选至多3%重量,例如柠檬酸、乳酸)、表面活性剂(特别是至多5%重量,优选非离子和/或阴离子表面活性剂)和水外,还优选包含溶剂(优选至多15%重量)以除去脂肪污物,且还包含例如增稠剂和防腐剂这样的化合物。此外,在优选用于光亮的不锈钢表面的产品中,包括极为精细的抛光结构。由此银抛光剂可以以酸性制品形式提供。特别地,为了除去硫化银的黑色沉积物,它们优选包含配位剂(例如硫脲、硫代硫酸钠)。典型的提供形式是抛光布、浸浴液、糊剂和液体。使用铜清洁剂和非铁金属清洁剂(例如用于铜锌合金和红古铜色)除去深度变色(氧化层)。它们一般具有弱碱性配方(优选含有氨)且通常包含抛光剂,且还优选包含铵肥皂和/或配位剂;
玻璃清洁剂和窗户清洁剂。这些产品优选用于从玻璃表面上除去污物,尤其是油腻污物。优选它们包含这样的化合物,例如阴离子和/或非离子表面活性剂(特别是至多5%重量)、氨和/或乙醇胺(特别是至多1%重量)、乙醇和/或2-丙醇、乙烯甘油醚类(特别是至多10-30%重量)、水、防腐剂、染料、防雾剂等;和
专用目的的清洁产品,实例是用于玻璃-陶瓷壁炉挂架的那些,并且还有地毯清洁剂和污渍去除剂。
汽车护理产品包括:
漆保护剂、漆抛光剂、漆清洁剂、洗涤保护剂、用于自动清洗的清洗剂、自动清洗和蜡产品、用于装饰金属的抛光剂、用于装饰金属的保护膜、塑料清洁剂、焦油去除剂、屏幕清洁剂、发动机清洁剂等。
化妆品包括:
(a)护肤化妆品,尤其是浴室产品、皮肤洗涤和清洁产品、护肤产品、眼用粉底、护唇用产品、指甲护理产品、私密护理产品、足护理产品;
(b)具有特殊效果的化妆品,尤其是防晒霜、晒成褐色产品、脱色素产品、除臭剂、止汗剂、脱毛发剂、剃毛产品、香料;
(c)牙科医疗化妆品,尤其是牙齿和口腔护理产品、牙修复体用粘着剂;和
(d)美容护发产品,尤其是洗发香波、护发产品、头发定型产品、头发整形产品和发色产品。
纺织品处理产品包括:
洗涤剂或织物调理剂,例如液体或固体形式。
空气清新剂和室内用香料包括:
优选包含挥发性且通常是溴到令人愉快气味的化合物的产品,这些化合物甚至可以以极小量有利地掩蔽令人不愉快的气味。用于生活区域的空气清新剂特别地包含天然和合成精油,例如松针油、柠檬油、桉叶油、薰衣草油等,其用量为,例如至多50%重量。作为气雾剂,它们倾向于包含少量这类精油,作为实例,用量低于5%或低于2%重量,但还包括这样的化合物,例如乙醛(特别是<0.5%重量)、异丙醇(特别是<5%重量)、矿物油(特别是<5%重量)和推进剂。其它呈现形式包括棒和块。典型地使用包含精油的凝胶浓缩物制备它们。还能够添加甲醛(用于防腐)和叶绿素(优选<5%重量)且还能够添加另外的成分。然而,空气清新剂不限于生活空间,而且还预用于汽车、橱柜、洗盘机、冰箱或鞋子和甚至其在真空吸尘器中的应用是可能的。例如在家庭(例如橱柜)中,除气味改进剂外,还可以使用消毒剂,其优选包含这样的化合物,例如磷酸钙、滑石粉、硬脂精和精油,这些产品采用例如小香囊这样的形式。
以下一系列实施例用于进一步说明本发明。
实施例1
(E/Z)-5,9-二甲基-9-羟基-癸烯-4-醛(I)
a)2,6-二甲基辛-7-炔-2,6-二醇(2)
将水(1593ml)装入反应器并添加硫酸(875g,8.7mol)。将溶液冷却至20℃。添加3,7-二甲基辛-6-烯-1-炔-3-醇(1,2.45kg,16.1mol)并将混合物在25℃搅拌48小时。
添加水(1.5升)和甲基叔丁基醚(1.6升)并将混合物搅拌10分钟。将层分离并用甲基叔丁基醚(1.6升)萃取水层。将有机层合并并用NaOH 2M(250ml,pH0)、饱和KHCO3溶液(700ml,pH8-9)和盐水(800ml)洗涤。将溶液用MgSO4干燥并在真空中浓缩。通过在20cm维格罗柱上蒸馏除去残留物3,7-二甲基辛-6-烯-1-炔-3-醇和挥发性副产物(b.p.35-104℃,0.4毫巴)。对粗产物进行刮膜蒸馏(150℃,0.06毫巴)得到(2)(1642g,69%收率),为淡黄色液体。产物静置后结晶。将样品从己烷中结晶得到白色晶体,m.p.48-49℃。
1H NMR:3.36(s,1H);2.40(s,1H);2.20(s,1H);1.67-1.39(m,6H);1.43(s,3H);1.16(s,6H)。13C NMR:88.5(s),71.7(d),71.6,68.1(2s),44.2,44.0(2t),30.2,29.6,29.5(3q),19.8(t)。
MS:137(10,M+-CH3,H2O),109(29),79(40),77(15),71(15),69(42),66(59),59(100),56(28),43(91),41(21)。
b)2,6-二甲基辛-7-烯-2,6-二醇(3)
将2,6-二甲基辛-7-炔-2,6-二醇(2,2.4kg,14.1mol)和甲苯(1.8升)装入装备有曝气搅拌子的反应器。添加用铅中毒的披钯活性碳(林德拉催化剂,25g),并将反应器首先用惰性气体然后用氢气进行冲洗。将混合物在0.1-0.2巴氢化7.5小时直到消耗了理论量的氢气。通过水浴使反应期间的温度保持在34-40℃。在反应结束时GC分析显示6%过度氢化的副产物。通过过滤将催化剂除去并将(3)的甲苯溶液用于下一合成步骤,未进行进一步处理。将(3)的样品从己烷中重结晶以用于光谱分析,m.p.46-47℃。
1H NMR:5.83(dd,J=17.4,10.8,1H);5.12(dd,J=17.4,1.5,1H);4.95(dd,J=10.8,1.5,1H);2.29(bs,2H);1.49-1.25(m,6H);1.2(s,3H);1.12(s,6H)。13C NMR:145.6(d),111.9(t),73.6,71.3(2s),44.5,43.1(2t),29.6,28.0(3q),19.0(t)。
MS:154(1,M+-H2O),121(16),81(35),71(100),69(25),68(45),59(36),56(36),55(18),43(53),41(17)。
c)(E/Z)-5,9-二甲基-9-羟基-癸烯-4-醛(I)
在具有搅拌器的压力容器(Büchi,5000ml)中,添加来自之前氢化反应的2,6-二甲基辛-7-烯-2,6-二醇在甲苯(3,2.25升,7mol)中的混合物,乙基乙烯基醚(1.26kg,17mol)和苯基膦酸(13g,82mmol)。将高压釜用氮气冲洗并预加压到2巴并且加热到150℃(压力4-6巴)30分钟。然后将温度升高到175℃(压力8-10巴)并保持50分钟。将反应混合物冷却并转移到10升夹套反应器中。添加水(3升)和HCl(2M,300ml)并将混合物在50℃搅拌直到GC分析显示混合物中(I)的缩醛完全氢化。将混合物用饱和KHCO3水溶液中和并分离各层。将水层用MtBE萃取,将有机层合并并用乙酸(10%,500ml)洗涤,用MgSO4干燥并在真空中浓缩。将粗产物进行刮膜蒸馏(150℃,0.06毫巴),得到(I)(1077g,78%收率),为淡橙色液体。
将粗物质在具有苏尔寿填料的50cm、1'直径柱上蒸馏(b.p.109℃,0.05毫巴),得到嗅觉纯的(I)(514g,37%收率)。折射率
1H NMR;E/Z异构体的混合物:9.73(t,J=1.77,1H);9.72(t,J=1.77,1H);5.07(t,J=7.07,2H);2.46-2.40(m,4H);2.34-2.25(m,4H);2.01(m,2H);1.94(m,2H);1.65(q,J=1.27,3H);1.61(bs,2H(OH));1.59(bs,3H);1.48-1.32(m,8H);1.18(s,6H);1.17(s,6H)。13C NMR;E/Z异构体的混合物:203.0,202.9(2d),137.3,137.2(2s),123.2,122.5(2d),71.2,71.1(2s),44.5,44.3,44.0,43.7,40.3,32.4(6t),29.6(4q),23.6(q),23.0,22.9,21.2,21.0(4t),16.3(q)。
MS;全部的E/Z异构体:180(1,M+-H2O),96(33),93(27),81(82),69(44),68(55),67(39),59(100),55(55),43(64),41(59)。
气味:花香,青香,铃兰香,羟基香茅醛香调
如果没有另外说明,所报告的NMR光谱在CDCl3中在400MHz下测定;化学位移是从TMS向低场以ppm为单位报告;耦合常数J的单位为Hz。如果没有另外说明,GC/MS分析使用ZB-5柱进行。所有纯化的产物结晶并作为白色固体分离或者通过真空蒸馏纯化并作为无色油分离,纯度通过GC/MS确定。用于嗅觉评价的样品通过在具有苏尔寿填料的蒸馏柱上精馏来纯化。
实施例2
在本实施例中,按照GB981,702实施例27的方法进行并且将产物分离并表征。
将晶体羟基芳樟醇(171g,0.993mol,m.p.46-47℃)溶于乙基乙烯基醚(240g,3.325mol)并置于PARR高压釜中。添加磷酸(0.6g)并将混合物在180℃加热30分钟。将混合物冷却至室温,用三乙胺(2.4ml)中和并在真空(100℃,14mm)中浓缩。将残留物(205.6g)添加到亚硫酸钠(500g)和水(2000ml)的混合物中并搅拌1小时。通过添加乙酸(2g)将pH设定至7,然后将混合物用MtBE萃取3次。将合并的醚萃取物在真空中浓缩,得到非醛成分(90.6g)。在该专利中,发明人报告为44g的非醛物质。将水层用30%的NaOH(1000ml)处理,同时用冰/水浴冷却混合物。然后将混合物(pH14)用MtBE萃取3次,将有机层合并,用碳酸氢钠溶液洗涤并浓缩。将黑色粘稠残留物(91.3g)(在该专利中发明人报告为182g)溶解在丙酮(500ml)中,并添加10%硫酸(200ml)。将混合物静置过夜。然后将混合物用水(2000ml)稀释并用MtBE萃取5次。将合并的醚萃取物用碳酸氢钠洗涤并在真空中浓缩。将粗物质通过蒸馏(bp.85℃,0.5毫巴)纯化,得到均匀分布的(E/Z)-5,9-二甲基癸-4,8-二烯醛和(E/Z)-5,9-二甲基癸-4,9-二烯醛(5.66g,3.16%收率)的混合物。折射率:nD 201.4682
气味:果香,苹果香,柑橘香,油脂味,醛香,金属味,微热铁味,持久的
1H NMR;异构体的混合物:9.76(q,J=1.77,4H);5.14-5.04(m,6H);4.69(m,4H);2.45(m,8H);2.33(m,8H);2.11-1.93(m,16H);1.74-1.66(m,18H);1.64-1.59(m,12H);1.57-1.47(m,4H)。13C NMR;异构体的混合物:202.92,202.85,202.83,202.79(4d),146.23,146.07(2s),137.41,137.29,137.21(4s),132.11,131.83(2s),124.47,124.42,123.21,123.18,122.48,122.40(6d),110.27,110.20(2t),44.55,44.35,44.32,39.99,39.54,37.98,37.69,32.29,31.75,26.95,26.80,26.23,26.19(14t),26.07,26.03,23.70,23.69,22.76(6q),21.24,21.21,21.07,21.03(4t),18.04,18.00,16.40,16.31(4q)。
MS 5,9-二甲基癸-4,9-二烯醛;全部的E/Z异构体:180(1,M+-H2O),96(55),81(100),79(34),69(41),68(97),67(66),55(95),53(35),41(95),39(37)。
MS 5,9-二甲基癸-4,8-二烯醛;全部的E/Z异构体:180(1,M+-H2O),137(1),136(1),93(14),69(100),67(11),55(24),53(11),43(1),41(66),39(11)。
实施例3
向装配有搅拌器、冷凝器和滴液漏斗的1000mL多颈烧瓶中装入180g羟基芳樟醇在180g甲苯中的溶液;0.9g磷酸(85%);和0.3g三乙醇胺。在搅拌下将烧瓶加热至125℃,并经过2小时添加150g二甘醇二乙烯基醚,并在保持该温度的同时搅拌混合物。添加后,将10g甲苯添加到烧瓶中并将混合物在相同温度下搅拌另外2.5小时。之后,将反应混合物在70℃用10g氯化钠在120g水中的溶液洗涤3次。在用10%碳酸氢钠水溶液和水洗涤之后,将甲苯蒸发掉并将残留物在真空中分馏,得到(E&Z)-9-羟基-5,9-二甲基癸-4-烯醛,为无色至淡黄色油。
实施例4
将焦亚硫酸钠(9.59g)溶于水并向其中添加9-羟基-5,9-二甲基癸-4-烯醛(10g)。将乙醇(10ml)添加到溶液中,混合物变为浑浊。将混合物在室温搅拌30分钟。有机物质的GC分析显示几乎所有的醛以其磺酸盐加合物形式存在于水相中。将混合物搅拌另外的30分钟,之后添加50ml的MtBE。分离各层并将水层用10ml MtBE萃取另外2次。水相的pH为4.4。取出一部分,冷冻干燥并进行分析:
1H NMR(MeOD);E/Z异构体的混合物:δ5.19(t,J=7.09,2H);4.25(m,2H);2.32-1.94(m,10H);1.77(m,2H);1.71(s,3H);1.65(s,3H);1.46(m,8H);1.18(s,12H)。13C NMR(MeOD);E/Z异构体的混合物:δ136.0,135.8(2s),124.0,123.3(2d),83.4(2d),70.1(2s),43.1,43.0,39.9,31.7,31.4(6t),27.8(4q),23.7,22.4,22.3(4t),22.2,14.66(2q)。mp>84℃分解。
之后,向剩余的样品中分批添加15%碳酸钠水溶液。气体析出表明磺酸盐已经分解。pH为7.1。分批添加更多的碳酸钠直到混合物pH达到9.45,之后将混合物温热到40℃30分钟。通过用MtBE萃取对略微碱性的水溶液进行后处理,并将有机相合并,用10%乙酸洗涤,干燥并浓缩,再次得到9-羟基-5,9-二甲基癸-4-烯醛。
实施例5
在精细香料中的应用
两种包含环己醛的精细香料,一种男士-型和一种女士-型,用作对比配方。
通过除去环己醛并用等量的如上表所示的香料组合物替代它来改性所述男士-型和一种女士-型香料以提供3种改性男士-型香料和3种改性女士-型香料。
将改性香料和对比配方各自置于吸墨纸上。由一组经过训练的调香师立刻以及在4小时蒸发后评定所述改性香料和对比配方的气味特征。
所有改性香料被评定为具有显著类似于对比配方的气味特征,证明上表中所示的香料配方适于在精细香料配制中作为环己烯的替代物。
在织物柔软剂中的应用
将未加香的织物柔软剂基料用环己醛加香以形成对比配方并用类似量的如上表中所示的各种香料组合物加香以生成测试配方。将加香的织物柔软剂组合物在水中稀释并且这些稀释的组合物的气味特征由一组经过训练的调香师评定。
从小组评定发现,测试配方显示出与对比配方显著类似的气味特征,证明上表中所示的香料配方适于在织物柔软剂配制中作为环己烯的替代物。
在沐浴露中的应用
将未加香的沐浴露基料用环己醛加香以形成对比配方并用类似量的如上表中所示的各种香料组合物加香以生成测试配方。将加香的沐浴露组合物在水中稀释并且这些稀释的组合物的气味特征由一组经过训练的调香师评定。
从小组评定发现,测试配方显示出与对比配方显著类似的气味特征,证明上表中所示的香料配方适于在沐浴露配制中作为环己烯的替代物。
在香波中的应用
将未加香的香波基料用环己醛加香以形成对比配方并用类似量的如上表中所示的各种香料组合物加香以生成测试配方。将加香的香波组合物在水中稀释并且这些稀释的组合物的气味特征由一组经过训练的调香师评定。
从小组评定发现,测试配方显示出与对比配方显著类似的气味特征,证明上表中所示的香料配方适于在香波配制中作为环己烯的替代物。
实施例6
在以下的香料配方中,5,9-二甲基-9-羟基-癸烯-4-醛或实施例5中描述的混合物和环己醛(Lyral TM)是可交换的成分。5,9-二甲基-9-羟基-癸烯-4-醛如同环己醛一样增加了香料组合物的体香、扩散性和光泽。
实施例7
在以下的香料配方中,5,9-二甲基-9-羟基-癸烯-4-醛或实施例5中描述的混合物和环己醛(Lyral TM)是可交换的成分。5,9-二甲基-9-羟基-癸烯-4-醛如同环己醛一样增加了香料组合物的体香、扩散性和光泽。
Claims (21)
3.权利要求2的香料混合物,其中化合物(I)与化合物(II)的重量/重量比例为99:1。
4.权利要求2的香料混合物,其中化合物(I)与化合物(II)的重量/重量比例为99.1:0.9;99.2:0.8;99.3:0.7;99.4:0.6;99.5:0.5;99.6:0.4;99.7:0.3;99.8:0.2;99.9:0.1;99.95:0.05;或99.99:0.01。
5.权利要求2-4中任一项的香料混合物,包含抗氧化剂。
6.香料组合物,包含权利要求1的化合物。
7.香料组合物,包含权利要求1的化合物或权利要求2-5中任一项的香料混合物和一种或多种选自2-亚环己基-2-苯基乙腈;4-(八氢-4,7-亚甲基-5H-茚-5-亚基)丁醛;4-甲基-2-(2-甲基丙基)四氢-2H-吡喃-4-醇;和2-(2-己基-3-氧代环戊基)乙酸甲酯的化合物。
8.权利要求6-7任一项的香料组合物,其中基于所述香料组合物的总重量,所述式(I)的化合物或香料混合物以1-30%重量的量存在于所述组合物中。
9.权利要求6-7任一项的香料组合物,其为铃兰香料组合物。
10.权利要求6-7任一项的香料组合物,包含至少一种另外的香料成分。
11.权利要求6-7任一项所定义的香料组合物,包含抗氧化剂。
12.个人护理或家庭护理组合物或精细香料组合物,包含权利要求1的化合物,权利要求2-5中任一项的香料混合物,或权利要求6-11任一项所定义的香料组合物。
13.权利要求12所述的个人护理或家庭护理组合物或精细香料组合物,包含抗氧化剂。
14.将铃兰气味香型赋予香料组合物或个人或家庭护理产品或精细香料的方法,该方法包括向其中添加权利要求1的化合物或权利要求2-5中任一项的香料混合物的步骤。
16.权利要求15的方法,其中所述保护的羟基选自乙酸酯、甲硅烷基醚或混合缩醛。
18.根据权利要求1的式(I)的化合物或根据权利要求2-5中任一项的香料混合物的用途,其作为环己醛替代品。
19.香料组合物,包含根据权利要求1的式(I)的化合物或根据权利要求2-5中任一项的香料混合物,其中所述组合物不含环己醛。
20.加香制品,其用根据权利要求1的式(I)的化合物或根据权利要求2-5中任一项的香料混合物加香。
21.权利要求20的加香制品,选自精细香料或个人或家庭护理产品。
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KR20160019441A (ko) | 2016-02-19 |
US9469590B2 (en) | 2016-10-18 |
MX2015015906A (es) | 2016-03-09 |
ZA201508404B (en) | 2020-01-29 |
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