JP2021065323A - Deodorant composition - Google Patents
Deodorant composition Download PDFInfo
- Publication number
- JP2021065323A JP2021065323A JP2019191458A JP2019191458A JP2021065323A JP 2021065323 A JP2021065323 A JP 2021065323A JP 2019191458 A JP2019191458 A JP 2019191458A JP 2019191458 A JP2019191458 A JP 2019191458A JP 2021065323 A JP2021065323 A JP 2021065323A
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- Prior art keywords
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- component
- hydrogen atom
- carbon atoms
- deodorant composition
- 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.)
- Ceased
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- 239000000203 mixture Substances 0.000 title claims abstract description 62
- 239000002781 deodorant agent Substances 0.000 title claims abstract description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 39
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000002304 perfume Substances 0.000 claims abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 5
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims abstract description 4
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims abstract description 4
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 4
- 239000003205 fragrance Substances 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 26
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 26
- 125000004122 cyclic group Chemical group 0.000 claims description 26
- 150000002430 hydrocarbons Chemical class 0.000 claims description 22
- -1 3-hexenyloxy group Chemical group 0.000 claims description 17
- 230000001877 deodorizing effect Effects 0.000 claims description 15
- 150000002576 ketones Chemical class 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- XTQZONYRNXFGCY-MLWJPKLSSA-N (2s)-4-[(2-methylpropan-2-yl)oxy]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC1CN[C@H](C(O)=O)C1 XTQZONYRNXFGCY-MLWJPKLSSA-N 0.000 claims description 2
- OQWHXHYZFMIILA-GDVGLLTNSA-N (2s)-4-acetyloxypyrrolidine-2-carboxylic acid Chemical compound CC(=O)OC1CN[C@H](C(O)=O)C1 OQWHXHYZFMIILA-GDVGLLTNSA-N 0.000 claims description 2
- RNXKXUOGQKYKTH-AKGZTFGVSA-N (2s)-4-methoxypyrrolidine-2-carboxylic acid Chemical compound COC1CN[C@H](C(O)=O)C1 RNXKXUOGQKYKTH-AKGZTFGVSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 238000004040 coloring Methods 0.000 abstract description 19
- 235000019645 odor Nutrition 0.000 description 48
- 239000000243 solution Substances 0.000 description 33
- 239000012459 cleaning agent Substances 0.000 description 17
- BSAIUMLZVGUGKX-UHFFFAOYSA-N 2-Nonenal Natural products CCCCCCC=CC=O BSAIUMLZVGUGKX-UHFFFAOYSA-N 0.000 description 16
- BSAIUMLZVGUGKX-FPLPWBNLSA-N 2-nonenal Chemical compound CCCCCC\C=C/C=O BSAIUMLZVGUGKX-FPLPWBNLSA-N 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- JZQKTMZYLHNFPL-BLHCBFLLSA-N (2E,4E)-deca-2,4-dienal Chemical compound CCCCC\C=C\C=C\C=O JZQKTMZYLHNFPL-BLHCBFLLSA-N 0.000 description 11
- JZQKTMZYLHNFPL-UHFFFAOYSA-N 2-trans-4-trans-decadienal Natural products CCCCCC=CC=CC=O JZQKTMZYLHNFPL-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 235000001014 amino acid Nutrition 0.000 description 8
- 150000001413 amino acids Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229940043350 citral Drugs 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 230000001953 sensory effect Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 4
- 235000018417 cysteine Nutrition 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 3
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical class O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 3
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 229930007744 linalool Natural products 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 238000003419 tautomerization reaction Methods 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- YGFGZTXGYTUXBA-UHFFFAOYSA-N (±)-2,6-dimethyl-5-heptenal Chemical compound O=CC(C)CCC=C(C)C YGFGZTXGYTUXBA-UHFFFAOYSA-N 0.000 description 2
- MOQGCGNUWBPGTQ-UHFFFAOYSA-N 2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde Chemical compound CC1=C(C=O)C(C)(C)CCC1 MOQGCGNUWBPGTQ-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 150000003935 benzaldehydes Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000008676 import Effects 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GVOWHGSUZUUUDR-UHFFFAOYSA-N methyl N-methylanthranilate Chemical compound CNC1=CC=CC=C1C(=O)OC GVOWHGSUZUUUDR-UHFFFAOYSA-N 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- QJJDNZGPQDGNDX-UHFFFAOYSA-N oxidized Latia luciferin Chemical compound CC(=O)CCC1=C(C)CCCC1(C)C QJJDNZGPQDGNDX-UHFFFAOYSA-N 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
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- 239000003973 paint Substances 0.000 description 2
- RUMOYJJNUMEFDD-UHFFFAOYSA-N perillyl aldehyde Chemical compound CC(=C)C1CCC(C=O)=CC1 RUMOYJJNUMEFDD-UHFFFAOYSA-N 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
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- 239000002904 solvent Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
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- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
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- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
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- JRJBVWJSTHECJK-LUAWRHEFSA-N (z)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one Chemical compound CC(=O)C(\C)=C/C1C(C)=CCCC1(C)C JRJBVWJSTHECJK-LUAWRHEFSA-N 0.000 description 1
- 0 *C(C1)CNC1C(O)=O Chemical compound *C(C1)CNC1C(O)=O 0.000 description 1
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- FVUGZKDGWGKCFE-UHFFFAOYSA-N 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethanone Chemical compound CC1(C)CCCC2=C1CC(C(C)=O)(C)C(C)C2 FVUGZKDGWGKCFE-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Abstract
Description
本発明は消臭剤組成物及びそれを用いた消臭方法に関する。 The present invention relates to a deodorant composition and a deodorizing method using the same.
アルデヒド類は揮発性成分の中で特に閾値が低く、ごく微量に存在するだけで認知されることから、様々な悪臭の原因物質となっている。例えば、2-ノネナール、2,4-デカジエナールはそれぞれ加齢臭、調理油臭の原因物質とされている。加えて、生魚臭、生肉臭、頭皮臭等にもアルデヒド類が多く含まれていることが一般に知られており、アルデヒド類の消臭に効果的な消臭剤が求められている。 Aldehydes have a particularly low threshold value among volatile components, and are recognized only in a very small amount, so that they are causative substances of various malodors. For example, 2-nonenal and 2,4-decadienal are considered to be the causative substances of aging odor and cooking oil odor, respectively. In addition, it is generally known that raw fish odors, raw meat odors, scalp odors, and the like also contain a large amount of aldehydes, and a deodorant effective for deodorizing aldehydes is required.
アルデヒド類を対象とした消臭技術としては、加齢臭の主要な原因物質であり不飽和アルデヒドの一種である2-ノネナールを対象としたものが多く開発されている。例えば特許文献１には、水及び低濃度のアミノ酸を含有する体臭除去用組成物が開示されている。また、特許文献２には、2-ノネナール等のアルデヒド類の消臭について、エタノールアミンが効果的であることが開示されている。 As a deodorizing technology for aldehydes, many have been developed for 2-nonenal, which is a major causative substance of aging odor and a kind of unsaturated aldehyde. For example, Patent Document 1 discloses a composition for removing body odor containing water and a low concentration of amino acids. Further, Patent Document 2 discloses that ethanolamine is effective for deodorizing aldehydes such as 2-nonenal.
特許文献１及び２を始めとする既存の消臭技術の多くは、その効果の発現に数時間〜数日間を要するものが多い。しかしながら、例えば「調理時に手についた魚の臭いをハンドソープを用いた手洗い中に落とす」、「頭皮の加齢臭をドライシャンプーの使用中に落とす」といった場面では、数十秒〜数分というごく短時間で悪臭を低減することが求められ、前記既存の消臭技術ではこのような要求に応えることができない。 Many of the existing deodorizing techniques such as Patent Documents 1 and 2 require several hours to several days for the effect to appear. However, for example, in situations such as "remove the smell of fish on your hands while washing your hands with a hand soap" or "remove the odor of scalp while using dry shampoo", it takes only a few tens of seconds to a few minutes. It is required to reduce bad odor in a short time, and the existing deodorizing technology cannot meet such a demand.
また、特許文献２において使用されているエタノールアミンは刺激性があり、更にそれ自身が強いアミン臭を持つため、消臭剤組成物に配合した際に使用感が損なわれるという問題がある。 Further, the ethanolamine used in Patent Document 2 is irritating and has a strong amine odor by itself, so that there is a problem that the feeling of use is impaired when blended in the deodorant composition.
かかる状況において、本発明者らはアルデヒド類に由来する臭気を即時的に低減する技術の開発を目指して鋭意検討した結果、プロリン又はその類縁体を高配合した消臭剤組成物が、アルデヒド類に由来する臭気を即時的に低減することを見出した。ところが、ここにおいて本発明者らは、消臭剤組成物中においてプロリン又はその類縁体と香料化合物とを併用すると、短時間のうちに着色してしまうという新たな問題が生ずることを見出した。市販の消臭剤では、香りを楽しむ目的で香料を配合することが多いことから、上記の問題は、消臭剤組成物を設計する上で大きな障壁となる。 In such a situation, the present inventors have diligently studied with the aim of developing a technique for immediately reducing the odor derived from aldehydes, and as a result, a deodorant composition containing a high amount of proline or its analog has been found in aldehydes. It has been found that the odor derived from is immediately reduced. However, here, the present inventors have found that when proline or an analog thereof is used in combination with a fragrance compound in a deodorant composition, a new problem of coloring occurs in a short time. Since commercially available deodorants often contain fragrances for the purpose of enjoying the scent, the above problems pose a major obstacle in designing a deodorant composition.
したがって本発明は、アルデヒド類に由来する臭気を即時的に低減することができ、消臭剤自身が不快な臭気を持たず、かつ配合した香料に由来する着色が抑制された消臭剤組成物に関するものである。 Therefore, the present invention can immediately reduce the odor derived from aldehydes, the deodorant itself does not have an unpleasant odor, and the coloration derived from the blended fragrance is suppressed. It is about.
そこで本発明者らは、プロリン又はその類縁体を配合した消臭剤組成物における着色という問題を解決すべく、更なる検討を行った結果、併用する香料種及びその比率を適切に選択することで、消臭剤組成物の着色を防止できることを見出した。 Therefore, the present inventors have conducted further studies in order to solve the problem of coloring in the deodorant composition containing proline or an analog thereof, and as a result, appropriately select the fragrance type to be used in combination and its ratio. It was found that the deodorant composition can be prevented from being colored.
本発明は、下記成分(A)〜(C)；
成分(A)：下記一般式(1)で表される複素環式化合物又はその塩
In the present invention, the following components (A) to (C);
Component (A): Heterocyclic compound represented by the following general formula (1) or a salt thereof
〔式中、Ｒ1は、水素原子、メトキシ基、アセトキシ基、tert-ブトキシ基又はアミノオキシ基を示す。〕
成分(B)：下記成分(b-1)と成分(b-2)との含有質量比(b-1)／(b-2)が１／６以下である香料組成物
成分(b-1)：炭素数６〜18のα,β-不飽和カルボニル香料化合物
成分(b-2)：成分(b-1)に該当しない香料化合物
成分(C)：水及びエタノールから選択される１種以上
を含有し、成分(A)の含有量が0.2質量％以上６質量％以下であり、成分(B)の含有量が0.01質量％以上1.4質量％以下である、消臭剤組成物を提供するものである。
[In the formula, R 1 represents a hydrogen atom, a methoxy group, an acetoxy group, a tert-butoxy group or an aminooxy group. ]
Component (B): Perfume composition component (b-1) in which the content mass ratio (b-1) / (b-2) of the following component (b-1) and component (b-2) is 1/6 or less. ): Α, β-unsaturated carbonyl fragrance compound having 6 to 18 carbon atoms Component (b-2): Fragrance compound not corresponding to component (b-1) Component (C): One or more selected from water and ethanol Provided is a deodorant composition containing 0.2% by mass or more and 6% by mass or less of the component (A) and 0.01% by mass or more and 1.4% by mass or less of the content of the component (B). It is a thing.
さらに本発明は、前記の消臭剤組成物を用いて、アルデヒド類に由来するニオイを消臭する消臭方法を提供するものである。 Furthermore, the present invention provides a deodorizing method for deodorizing odors derived from aldehydes by using the above-mentioned deodorant composition.
本発明の消臭剤組成物は、アルデヒド類に由来するニオイを即時的に低減することができ、消臭剤自身が不快な臭気を持たず、かつ、配合した香料に由来する着色を防止することができるものである。 The deodorant composition of the present invention can immediately reduce the odor derived from aldehydes, the deodorant itself does not have an unpleasant odor, and the coloring derived from the blended fragrance is prevented. It is something that can be done.
〔成分(A)：一般式(1)で表される複素環式化合物又はその塩〕
本発明の消臭剤組成物は、成分(A)として下記一般式(1)で表される複素環式化合物又はその塩を含有する。
[Component (A): Heterocyclic compound represented by the general formula (1) or a salt thereof]
The deodorant composition of the present invention contains a heterocyclic compound represented by the following general formula (1) or a salt thereof as a component (A).
〔式中、Ｒ1は、水素原子、メトキシ基、アセトキシ基、tert-ブトキシ基又はアミノオキシ基を示す。〕 [In the formula, R 1 represents a hydrogen atom, a methoxy group, an acetoxy group, a tert-butoxy group or an aminooxy group. ]
Ｒ1としては、入手容易性の観点から、水素原子が好ましい。 As R 1 , a hydrogen atom is preferable from the viewpoint of availability.
成分(A)の具体例としては、例えば、プロリン、4-メトキシプロリン、4-アセトキシプロリン、4-tert-ブトキシプロリン等、及びそれらの塩が挙げられる。これらのうち、入手容易性の観点から、プロリン、及びプロリンと塩酸等の無機酸又はリンゴ酸、クエン酸、乳酸等の有機酸との塩から選ばれる１種以上が好ましい。 Specific examples of the component (A) include proline, 4-methoxyproline, 4-acetoxyproline, 4-tert-butoxyproline and the like, and salts thereof. Of these, from the viewpoint of availability, one or more selected from proline and a salt of proline and an inorganic acid such as hydrochloric acid or an organic acid such as malic acid, citric acid, and lactic acid is preferable.
成分(A)は、単独で又は２種以上を組み合わせて用いることができる。本発明の消臭剤組成物中における成分(A)の含有量は、アルデヒド類に由来するニオイに対する消臭性能の観点から、0.2質量％以上であって、好ましくは0.6質量％以上、より好ましくは1.2質量％以上、更に好ましくは２質量％以上であり、また、消臭剤自身の臭気の抑制の観点から、６質量％以下、より好ましくは４質量％以下、更に好ましくは3.5質量％以下である。 The component (A) can be used alone or in combination of two or more. The content of the component (A) in the deodorant composition of the present invention is 0.2% by mass or more, preferably 0.6% by mass or more, more preferably 0.6% by mass or more, from the viewpoint of deodorizing performance against odors derived from aldehydes. Is 1.2% by mass or more, more preferably 2% by mass or more, and from the viewpoint of suppressing the odor of the deodorant itself, 6% by mass or less, more preferably 4% by mass or less, still more preferably 3.5% by mass or less. Is.
〔成分(B)：香料組成物〕
成分(B)の香料組成物は、成分(A)と併用することによる着色を防止する観点から、下記成分(b-1)と成分(b-2)との含有質量比(b-1)／(b-2)を１／６以下とすることが必要である。
成分(b-1)：炭素数６〜18のα,β-不飽和カルボニル香料化合物
成分(b-2)：成分(b-1)に該当しない香料化合物
[Ingredient (B): fragrance composition]
The fragrance composition of the component (B) has a mass ratio (b-1) of the following component (b-1) and the component (b-2) from the viewpoint of preventing coloring when used in combination with the component (A). It is necessary to set / (b-2) to 1/6 or less.
Component (b-1): α, β-unsaturated carbonyl fragrance compound with 6 to 18 carbon atoms Component (b-2): Fragrance compound not corresponding to component (b-1)
（成分(b-1)：炭素数６〜18のα,β-不飽和カルボニル香料化合物）
成分(b-1)は、成分(A)と併用することによって着色を生ずる香料化合物であるが、香調のバリエーションを増やすという観点から、前記条件を満たす範囲であれば、使用者が容易に認知できる程度の着色を生ずることなく、含有することができる。成分(b-1)としては、下記(b-1-1)〜(b-1-6)が挙げられ、成分(b-1)を含有する場合、これらのいずれか１種又は２種以上を含有することができる。
(b-1-1)一般式(2)で表されるケトエノール互変異性化が可能なα,β-不飽和アルデヒド
(b-1-2)一般式(3)で表されるケトエノール互変異性化が可能なα,β,γ,δ-不飽和アルデヒド、
(b-1-3)一般式(4)で表されるケトエノール互変異性化が可能なα,β-不飽和ケトン
(b-1-4)一般式(5)で表されるケトエノール互変異性化が可能なα,β,γ,δ-不飽和ケトン
(b-1-5)一般式(6)で表されるベンズアルデヒド類縁体
(b-1-6)一般式(7)で表されるシンナムアルデヒド類縁体
(Component (b-1): α, β-unsaturated carbonyl fragrance compound with 6 to 18 carbon atoms)
The component (b-1) is a fragrance compound that causes coloring when used in combination with the component (A). However, from the viewpoint of increasing the variation of the fragrance tone, the user can easily use the component (b-1) as long as the above conditions are satisfied. It can be contained without causing recognizable coloring. Examples of the component (b-1) include the following (b-1-1) to (b-1-6), and when the component (b-1) is contained, any one or two or more of these are included. Can be contained.
(b-1-1) Keto-enol represented by the general formula (2) α, β-unsaturated aldehyde capable of tautomerization
(b-1-2) Keto-enol represented by the general formula (3) α, β, γ, δ-unsaturated aldehyde, which can be tautomerized,
(b-1-3) Keto-enol represented by the general formula (4) α, β-unsaturated ketone capable of tautomerization
(b-1-4) Keto-enol represented by the general formula (5) α, β, γ, δ-unsaturated ketone capable of tautomerization
(b-1-5) Benzaldehyde analog represented by the general formula (6)
(b-1-6) Cinnamaldehyde analog represented by the general formula (7)
成分(b-1-1)は、一般式(2)で表されるケトエノール互変異性化が可能なα,β-不飽和アルデヒドである。 The component (b-1-1) is an α, β-unsaturated aldehyde capable of tautomerizing keto-enol represented by the general formula (2).
〔式中、Ｒ2〜Ｒ4は、それぞれ独立して、水素原子若しくは炭素数１〜10の炭化水素基を示し、又はＲ2〜Ｒ4のうち２つが結合して環状構造を形成してもよい。〕 [In the formula, R 2 to R 4 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, or two of R 2 to R 4 are bonded to form a cyclic structure. May be good. ]
一般式(2)において、Ｒ2〜Ｒ4の炭素数１〜10の炭化水素基は、直鎖状、分岐鎖状、環状のいずれであってもよく、飽和でも不飽和でもよい。また、Ｒ2〜Ｒ4のうち２つが結合して形成する環状構造としては、６員環が好ましい。 In the general formula (2), the hydrocarbon groups having 1 to 10 carbon atoms of R 2 to R 4 may be linear, branched or cyclic, and may be saturated or unsaturated. Further, as the cyclic structure formed by combining two of R 2 to R 4, a 6-membered ring is preferable.
成分(b-1-1)としては、炭素数６〜14であるものが好ましく、具体例としては、シトラール、ペリラアルデヒド、シクロシトラール等が挙げられる。 The component (b-1-1) preferably has 6 to 14 carbon atoms, and specific examples thereof include citral, perillaldehyde, and cyclocitral.
成分(b-1-2)は、一般式(3)で表されるケトエノール互変異性化が可能なα,β,γ,δ-不飽和アルデヒドである。 The component (b-1-2) is an α, β, γ, δ-unsaturated aldehyde capable of tautomerizing keto-enol represented by the general formula (3).
〔式中、Ｒ5〜Ｒ7は、それぞれ独立して、水素原子又は炭素数１〜４の炭化水素基を示し、又はＲ5〜Ｒ7のうち２つが結合して環状構造を形成してもよい。〕 [In the formula, R 5 to R 7 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms, or two of R 5 to R 7 are bonded to form a cyclic structure. May be good. ]
Ｒ5〜Ｒ7の炭素数１〜４の炭化水素基は、直鎖状、分岐鎖状、環状のいずれであってもよく、飽和でも不飽和でもよい。また、Ｒ5〜Ｒ7のうち２つが結合して形成する環状構造としては６員環が好ましい。 The hydrocarbon groups having 1 to 4 carbon atoms of R 5 to R 7 may be linear, branched or cyclic, and may be saturated or unsaturated. Further, a 6-membered ring is preferable as the cyclic structure formed by combining two of R 5 to R 7.
成分(b-1-2)としては、炭素数６〜10であるものが好ましく、具体例としては、サフラナール等が挙げられる。 The component (b-1-2) preferably has 6 to 10 carbon atoms, and specific examples thereof include safranal and the like.
成分(b-1-3)は、一般式(4)で表されるケトエノール互変異性化が可能なα,β-不飽和ケトンである。 The component (b-1-3) is an α, β-unsaturated ketone capable of tautomerizing keto-enol represented by the general formula (4).
〔式中、Ｒ8、Ｒ9、Ｒ11、Ｒ12及びＲ13は、それぞれ独立して、水素原子若しくは炭素数１〜９の炭化水素基を示し、Ｒ10は、水素原子、ヒドロキシ基若しくはヒドロキシ基を有してもよい炭素数１〜９の炭化水素基を示し、又はＲ8〜Ｒ13のうち２つが結合してヘテロ原子としての酸素を含んでもよい環状構造を１以上形成してもよい。〕 [In the formula, R 8 , R 9 , R 11 , R 12 and R 13 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 9 carbon atoms, and R 10 is a hydrogen atom, a hydroxy group or It represents a hydrocarbon group having 1 to 9 carbon atoms which may have a hydroxy group, or two of R 8 to R 13 are bonded to form one or more cyclic structures which may contain oxygen as a hetero atom. May be good. ]
一般式(4)において、Ｒ8、Ｒ9、Ｒ11、Ｒ12及びＲ13の炭素数１〜９の炭化水素基としては、直鎖状、分岐鎖状、環状のいずれであってもよく、飽和でも不飽和でもよい。Ｒ10の炭素数１〜９の炭化水素基としては、直鎖状、分岐鎖状、環状のいずれであってもよく、飽和でも不飽和でもよい。また、Ｒ8〜Ｒ13のうち２つが結合して形成するヘテロ原子としての酸素を含んでもよい環状構造としては、５員環及び６員環が好ましい。 In the general formula (4), the hydrocarbon groups having 1 to 9 carbon atoms of R 8 , R 9 , R 11 , R 12 and R 13 may be linear, branched or cyclic. , Saturated or unsaturated. The hydrocarbon group having 1 to 9 carbon atoms of R 10 may be linear, branched or cyclic, and may be saturated or unsaturated. Further, as a cyclic structure which may contain oxygen as a hetero atom formed by bonding two of R 8 to R 13, a 5-membered ring and a 6-membered ring are preferable.
成分(b-1-3)としては、炭素数６〜17であるものが好ましく、具体例としては、l-カルボン、シスジャスモン 、ジヒドロジャスモン、(Z)-3,4,5,6,6-ペンタメチレンヘプト-3-エン-2-オン、1-(5,5-ジメチル-1-シクロヘキセニル)ペント-4-エン-1-オン、δ-ダマスコン、α-イオノン、α-ダマスコン、イソダマスコン、β-ダマスコン、1,1,2,3,3-ペンタメチル-2,5,6,7-テトラヒドロインデン-4-オン、1-(スピロ[4.5]デカ-7-エン-7-イル)ペント-4-エン-1-オン、ノートカトン、アリル-α-イオノン、4-アセチル-6-tert-ブチル-1,1-ジメチルインダン、シクロテン、フラネオール、イロン、エチルマルトール、マルトール、メチルセドリルケトン、γ-ダマスコン、γ-イオノン、イソジャスモン、γ-メチルイオノン、α-イソメチルイオノン等が挙げられる。 The component (b-1-3) preferably has 6 to 17 carbon atoms, and specific examples thereof include l-carboxylic, cis jasmon, dihydro jasmon, and (Z) -3,4,5,6,6. -Pentamethylenehepto-3-en-2-one, 1- (5,5-dimethyl-1-cyclohexenyl) pent-4-en-1-one, δ-damasconone, α-ionone, α-damascone, Isodamascone, β-damascone, 1,1,2,3,3-pentamethyl-2,5,6,7-tetrahydroinden-4-one, 1- (spiro [4.5] deca-7-en-7-yl) Pent-4-en-1-one, notecatone, allyl-α-ionone, 4-acetyl-6-tert-butyl-1,1-dimethylindane, cycloten, flaneol, iron, ethylmaltor, maltol, methylsedrill ketone , Γ-Damascone, γ-ionone, isojasmon, γ-methylionone, α-isomethylionone and the like.
成分(b-1-4)は一般式(5)で表されるケトエノール互変異性化が可能なα,β,γ,δ-不飽和ケトンである。 The component (b-1-4) is an α, β, γ, δ-unsaturated ketone capable of tautomerizing keto-enol represented by the general formula (5).
〔式中、Ｒ14〜Ｒ19は、それぞれ独立して、水素原子若しくは炭素数１〜７の炭化水素基を示し、又はＲ14〜Ｒ19のうち２つが結合して環状構造を形成してもよい。〕 [In the formula, R 14 to R 19 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 7 carbon atoms, or two of R 14 to R 19 are bonded to form a cyclic structure. May be good. ]
一般式(5)において、Ｒ14〜Ｒ19の炭素数１〜７の炭化水素基としては、直鎖状、分岐鎖状、環状のいずれであってもよく、飽和でも不飽和でもよい。また、Ｒ14〜Ｒ19のうち２つが結合して形成する環状構造としては、６員環が好ましい。 In the general formula (5), the hydrocarbon group having 1 to 7 carbon atoms of R 14 to R 19 may be linear, branched or cyclic, and may be saturated or unsaturated. Further, as the cyclic structure formed by combining two of R 14 to R 19, a 6-membered ring is preferable.
成分(b-1-4)としては、炭素数10〜15であるものが好ましく、具体例としては、ダマセノン、β-イオノン、β-メチルイオノン等が挙げられる。 The component (b-1-4) preferably has 10 to 15 carbon atoms, and specific examples thereof include damascenone, β-ionone, and β-methylionone.
成分(b-1-5)は、一般式(6)で表されるベンズアルデヒド類縁体である。 The component (b-1-5) is a benzaldehyde analog represented by the general formula (6).
〔式中、Ｒ20は、水素原子、ヒドロキシ基、メチル基、メトキシ基、エトキシ基、3-ヘキセニルオキシ基、フェニル基若しくはベンジルオキシ基を示し、Ｒ21は、水素原子、メチル基、ヒドロキシ基、アミノ基若しくはメチルアミノ基を示し、Ｒ22及びＲ23は、それぞれ独立して、水素原子、ヒドロキシ基、メトキシ基、エトキシ基、メチレンジオキシ基、ニトロ基若しくは炭素数１〜９の炭化水素基を示し、Ｒ24は、水素原子、ニトロ基若しくは炭素数１〜９の炭化水素を示し、Ｒ25は、水素原子若しくは炭素数１〜５の炭化水素基を示し、又はＲ22〜Ｒ25のうち２つが結合してヘテロ原子としての酸素を含んでもよい環状構造を形成してもよい。〕 [In the formula, R 20 represents a hydrogen atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, a 3-hexenyloxy group, a phenyl group or a benzyloxy group, and R 21 is a hydrogen atom, a methyl group or a hydroxy group. , Amino group or methylamino group, and R 22 and R 23 are independently hydrogen atom, hydroxy group, methoxy group, ethoxy group, methylenedioxy group, nitro group or hydrocarbon having 1 to 9 carbon atoms. Group is indicated, R 24 indicates a hydrogen atom, a nitro group or a hydrocarbon having 1 to 9 carbon atoms, R 25 indicates a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, or R 22 to R 25. Two of them may be bonded to form a cyclic structure which may contain oxygen as a hetero atom. ]
一般式(6)において、Ｒ22及びＲ23の炭素数１〜９の炭化水素としては、直鎖状、分岐鎖状、環状のいずれであってもよく、飽和でも不飽和でもよい。Ｒ24の炭素数１〜５の炭化水素基としては、直鎖状、分岐鎖状、環状のいずれであってもよく、飽和でも不飽和でもよい。また、Ｒ22〜Ｒ25のうち２つが結合して形成するヘテロ原子としての酸素を含んでもよい環状構造としては、６員環が好ましい。 In the general formula (6), the hydrocarbons having 1 to 9 carbon atoms of R 22 and R 23 may be linear, branched or cyclic, and may be saturated or unsaturated. The hydrocarbon group having 1 to 5 carbon atoms of R 24 may be linear, branched or cyclic, and may be saturated or unsaturated. Further, as a cyclic structure which may contain oxygen as a hetero atom formed by bonding two of R 22 to R 25, a 6-membered ring is preferable.
成分(b-1-5)としては、炭素数７〜18であるものが好ましく、具体例としては、ベンズアルデヒド、4-イソプロピルベンズアルデヒド、4-メチルベンズアルデヒド 、アニスアルデヒド、バニリン、エチルバニリン、アセトフェノン、ベンゾフェノン、メチル2-ナフチルケトン、4-アセチルトルエン、ピペロナール、アントラニル酸メチル、N-メチルアントラニル酸メチル、トラセオライド、セレストリド、ファントリド、トナリド、p-メトキシアセトフェノン、サリチル酸cis-3-ヘキセン-1-イル、サリチル酸エチル、サリチル酸ベンジル、サリチル酸メチル、バニリン酸、ムスクケトン、安息香酸、安息香酸エチル、安息香酸ベンジル、安息香酸メチル等が挙げられる。 The component (b-1-5) preferably has 7 to 18 carbon atoms, and specific examples thereof include benzaldehyde, 4-isopropylbenzaldehyde, 4-methylbenzaldehyde, anisaldehyde, vanillin, ethylvanillin, acetophenone, and benzophenone. , Methyl 2-naphthylketone, 4-acetyltoluene, piperonal, methyl anthranilate, methyl N-methylanthranylate, tratheolide, cerestride, phantolide, tonalide, p-methoxyacetophenone, cis-3-hexen-1-yl salicylate, salicylate Examples thereof include ethyl, benzyl salicylate, methyl salicylate, vaniphosphate, muskketone, benzoic acid, ethyl benzoate, benzyl benzoate, methyl benzoate and the like.
成分(b-1-6)は、一般式(7)で表されるシンナムアルデヒド類縁体である。 The component (b-1-6) is a cinnamaldehyde analog represented by the general formula (7).
〔式中、Ｒ26は、水素原子又はメチル基を示し、Ｒ27は、水素原子又は炭素数１〜６の炭化水素基を示し、Ｒ28〜Ｒ30は、それぞれ独立して、水素原子、メトキシ基若しくはメチレンジオキシ基を示し、Ｒ28〜Ｒ30のうち２つが結合してヘテロ原子としての酸素を含んでもよい環状構造を形成してもよい。〕 [In the formula, R 26 represents a hydrogen atom or a methyl group, R 27 represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, and R 28 to R 30 are independent hydrogen atoms, respectively. It may show a methoxy group or a methylenedioxy group, and two of R 28 to R 30 may be bonded to form a cyclic structure which may contain oxygen as a hetero atom. ]
一般式(7)において、Ｒ27の炭素数１〜６の炭化水素基としては、直鎖状、分岐鎖状、環状のいずれであってもよく、飽和でも不飽和でもよい。また、Ｒ28〜Ｒ30のうち２つが結合して形成するヘテロ原子としての酸素を含んでもよい環状構造としては、６員環が好ましい。 In the general formula (7), the hydrocarbon group having 1 to 6 carbon atoms of R 27 may be linear, branched or cyclic, and may be saturated or unsaturated. Further, as a cyclic structure which may contain oxygen as a hetero atom formed by bonding two of R 28 to R 30, a 6-membered ring is preferable.
成分(b-1-6)としては、炭素数９〜15であるものが好ましく、具体例としては、ヘキシルシンナムアルデヒド、シンナムアルデヒド、2-メトキシシンナムアルデヒド、アミルシンナムアルデヒド、ピペロニルメチルケトン等が挙げられる。 The component (b-1-6) preferably has 9 to 15 carbon atoms, and specific examples thereof include hexyl cinnamaldehyde, cinnamaldehyde, 2-methoxycinnamaldehyde, amilcinnamaldehyde, and piperonyl methyl ketone. Can be mentioned.
本発明の消臭剤組成物中における成分(b-1)の含有量は、着色防止の観点から、好ましくは0.2質量％以下、より好ましくは0.1質量％以下、更に好ましくは0.01質量％以下、更に好ましくは0.005質量％以下であり、更には成分(b-1)を含有しないことが好ましい。 The content of the component (b-1) in the deodorant composition of the present invention is preferably 0.2% by mass or less, more preferably 0.1% by mass or less, still more preferably 0.01% by mass or less, from the viewpoint of preventing coloration. More preferably, it is 0.005% by mass or less, and further preferably it does not contain the component (b-1).
また、成分(A)と成分(b-1)の含有質量比(b-1)／(A)は、両者の併用による着色防止の観点から、好ましくは１／３以下、より好ましくは１／６以下、更に好ましくは１／10以下、更に好ましくは０である。 Further, the content mass ratio (b-1) / (A) of the component (A) and the component (b-1) is preferably 1/3 or less, more preferably 1 /, from the viewpoint of preventing coloration by the combined use of both. It is 6 or less, more preferably 1/10 or less, still more preferably 0.
（成分(b-2)：成分(b-1)に該当しない香料化合物）
成分(b-2)は、成分(A)と併用しても着色を生じない香料化合物である。成分(b-2)としては、以下の成分(b-2-1)〜(b-2-3)が挙げられ、これらのいずれかを単独で又は２種以上を組み合わせて用いることができる。
成分(b-2-1)：α,β-不飽和アルデヒドに該当しないアルデヒド
成分(b-2-2)：α,β-不飽和ケトンに該当しないケトン
成分(b-2-3)：アルデヒド及びケトンに該当しないアルコール、エステル、エーテル又は炭化水素
(Component (b-2): Perfume compound that does not correspond to component (b-1))
The component (b-2) is a fragrance compound that does not cause coloring even when used in combination with the component (A). Examples of the component (b-2) include the following components (b-2-1) to (b-2-3), and any one of these can be used alone or in combination of two or more.
Component (b-2-1): Aldehyde not corresponding to α, β-unsaturated aldehyde Component (b-2-2): Ketone component not corresponding to α, β-unsaturated ketone (b-2-3): Aldehyde And alcohols, esters, ethers or hydrocarbons that do not correspond to ketones
成分(b-2-1)はα,β-不飽和アルデヒドに該当しないアルデヒドである。成分(b-2-1)の具体例としては、3-(1,3-ベンゾジオキソール-5-イル)-2-メチルプロパナール、フェニルアセトアルデヒド、ジメチル-3-シクロヘキセン-1-カルボアルデヒド、シトロネラール、2,6-ジメチル-5-ヘプテナール、2-シクロヘキシルプロパナール、シトロネロキシアセトアルデヒド、4-[(オクタヒドロ-4,7-メタノ-5H-インデン)-5-イリデン]ブタナール、シクラメンアルデヒド、3-(4-メトキシフェニル)-2-メチルプロパナール、トリメチルウンデセナール、ヒドロキシシトロネラール、2-エチル-α,α-ジメチルベンゼンプロパナール 、1-メチル-4-(4-メチルペンチル)-3-シクロヘキセン-1-カルボアルデヒド、テトラヒドロシトラール等が挙げられる。 The component (b-2-1) is an aldehyde that does not correspond to α, β-unsaturated aldehyde. Specific examples of the component (b-2-1) include 3- (1,3-benzodioxol-5-yl) -2-methylpropionaldehyde, phenylacetaldehyde, and dimethyl-3-cyclohexene-1-carbaldehyde. , Citroneral, 2,6-dimethyl-5-heptenal, 2-cyclohexylpropanaldehyde, citroneroxyacetaldehyde, 4-[(octahydro-4,7-methano-5H-inden) -5-iriden] butanal, cyclamenaldehyde, 3- (4-methoxyphenyl) -2-methylpropanal, trimethylundesenal, hydroxycitroneral, 2-ethyl-α, α-dimethylbenzenepropanal, 1-methyl-4- (4-methylpentyl) -3-Cyclohexene-1-carbaldehyde, tetrahydrocitral and the like can be mentioned.
成分(b-2-2)はα,β-不飽和ケトンに該当しないケトンである。成分(b-2-2)の具体例としては、2-アセチル-2,3,8,8-テトラメチル-1,2,3,4,5,6,7,8-オクタヒドロナフタレン、4-(4-ヒドロキシフェニル)ブタン-2-オン、メチルベンゾジオキシエピノン、カンファー、l-メントン、(5E)-3-メチルシクロペンタデカ-5-エン-1-オン、6-メチル-5-ヘプテン-2-オン、ジヒドロ-β-イオノン、メチルジヒドロジャスモネート、(3R)-3α-メチルシクロペンタデカノン、2,5,5-トリメチル-2-ペンチルシクロペンタノン等が挙げられる。 The component (b-2-2) is a ketone that does not correspond to an α, β-unsaturated ketone. Specific examples of the component (b-2-2) are 2-acetyl-2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalene, 4 -(4-Hydroxyphenyl) butane-2-one, methylbenzodioxyepinone, camphor, l-mentone, (5E) -3-methylcyclopentadeca-5-en-1-one, 6-methyl-5 -Heptene-2-one, dihydro-β-ionone, methyldihydrojasmonate, (3R) -3α-methylcyclopentadecanone, 2,5,5-trimethyl-2-pentylcyclopentanone and the like.
成分(b-2-3)はアルデヒド及びケトンに該当しないアルコール、エステル、エーテル又は炭化水素である。成分(b-2-3)の具体例としては、リナロール、フェニルエチルアルコール、酢酸ベンジル、ジヒドロミルセノール、酢酸リナリル、cis-3-ヘキセノール、酢酸スチラリル、ターピネオール、(2-メチルブチルオキシ)酢酸2-プロペニル、ゲラニオール、酢酸2-(tert-ブチル)シクロヘキシル、ローズオキシド、γ-デカラクトン、γ-ウンデカラクトン、エチレンブラシレート、 酢酸イソボルニル、15-ペンタデカノラクトン、メチル酪酸エチル、テトラヒドロリナロール、5-フェニル-1-ペンタノール、ネロール、プロピオン酸トリシクロデセニル、酢酸イソアミル、酪酸エチル、酢酸ネリル、炭酸エチル2-(1,1-ジメチルエチル)シクロヘキシル、(4aR,5R,7aS,9R)-オクタヒドロ-2,2,5,8,8,9a-ヘキサメチル-4h-4a,9-メタノアズレノ(5,6-d)-1,3-ジオキソール、3-[2,2,3-トリメチルビシクロ[2.2.1]ヘプタ-5-イル]シクロヘキサノール、2,6-ジメチルヘプタン-2-オール、α-ピネン、β-ピネン、ミルセン、ターピノレン、オシメン、リモネン、カンフェン、p-サイメン、セドレン、β-カリオフィレン等が挙げられる。 The component (b-2-3) is an alcohol, ester, ether or hydrocarbon that does not correspond to aldehydes and ketones. Specific examples of the component (b-2-3) include linalool, phenylethyl alcohol, benzyl acetate, dihydromilsenol, linaryl acetate, cis-3-hexenol, styralyl acetate, tarpineol, (2-methylbutyloxy) acetic acid. 2-propenyl, geraniol, 2- (tert-butyl) cyclohexyl acetate, rose oxide, γ-decalactone, γ-undecalactone, ethylene brushate, isobornyl acetate, 15-pentadecanolactone, ethyl methylbutyrate, tetrahydrolinalool, 5-Phenyl-1-pentanol, linalool, tricyclodecenyl propionate, isoamyl acetate, ethyl butyrate, neryl acetate, ethyl 2- (1,1-dimethylethyl) cyclohexyl, (4aR, 5R, 7aS, 9R) )-Octahydro-2,2,5,8,8,9a-Hexamethyl-4h-4a, 9-Metanoazureno (5,6-d) -1,3-dioxol, 3- [2,2,3-trimethylbicyclo [2.2.1] Hepta-5-yl] Cyclohexanol, 2,6-dimethylheptan-2-ol, α-pinene, β-pinene, milsen, turpinolene, osimene, linalool, camphene, p-cymen, cedren, β -Cariophyllen etc. can be mentioned.
成分(b-2)としては、成分(A)と併用した際の香調の安定性の観点から、成分(b-2-1)、成分(b-2-2)及び(b-2-3)から選ばれる１種以上が好ましく、成分(b-2-2)及び(b-2-3)から選ばれる１種以上がより好ましく、成分(b-2-3)から選ばれる１種以上が更に好ましい。 As the component (b-2), the component (b-2-1), the component (b-2-2) and (b-2-2) are used from the viewpoint of the stability of the incense tone when used in combination with the component (A). One or more selected from 3) is preferable, one or more selected from components (b-2-2) and (b-2-3) is more preferable, and one selected from component (b-2-3). The above is more preferable.
本発明の消臭剤組成物中における成分(b-2)の含有量は、香調のバリエーションを増やすという観点から、好ましくは0.01質量％以上、より好ましくは0.1質量％以上である。また、分散安定性の観点から、好ましくは1.4質量％以下、より好ましくは１質量％以下である。 The content of the component (b-2) in the deodorant composition of the present invention is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, from the viewpoint of increasing the variation of the aroma tone. Further, from the viewpoint of dispersion stability, it is preferably 1.4% by mass or less, more preferably 1% by mass or less.
成分(b-1)と成分(b-2)の含有質量比(b-1)／(b-2)は、成分(A)と成分(b-1)の併用による着色防止の観点から、１／６以下であって、好ましくは１／10以下、より好ましくは１／12以下、更に好ましくは１／24以下、更に好ましくは０である。 The content mass ratio (b-1) / (b-2) of the component (b-1) and the component (b-2) is determined from the viewpoint of preventing coloration by the combined use of the component (A) and the component (b-1). It is 1/6 or less, preferably 1/10 or less, more preferably 1/12 or less, still more preferably 1/24 or less, still more preferably 0.
本発明の消臭剤組成物中における、成分(b-1)と成分(b-2)からなる成分(B)の総含有量は、香りの認知しやすさの観点から、好ましくは0.01質量％以上、より好ましくは0.1質量％以上である。また、分散安定性の観点から、好ましくは1.4質量％以下、より好ましくは１質量％以下である。 The total content of the component (B) composed of the component (b-1) and the component (b-2) in the deodorant composition of the present invention is preferably 0.01 mass by mass from the viewpoint of recognizing the scent. % Or more, more preferably 0.1% by mass or more. Further, from the viewpoint of dispersion stability, it is preferably 1.4% by mass or less, more preferably 1% by mass or less.
〔成分(C)：水及びエタノールから選択される１種以上〕
成分(C)は消臭剤組成物のキャリアであり、水、エタノール、又はそれらの混合物が用いられる。
[Component (C): One or more selected from water and ethanol]
Ingredient (C) is the carrier of the deodorant composition, and water, ethanol, or a mixture thereof is used.
本発明の消臭剤組成物中における成分(C)の含有量は、安定な分散状態を維持する観点から、好ましくは40質量％以上、より好ましくは70質量％以上である。また、十分な消臭効果を得る観点から、好ましくは99質量％以下、より好ましくは92質量％以下である。 The content of the component (C) in the deodorant composition of the present invention is preferably 40% by mass or more, more preferably 70% by mass or more, from the viewpoint of maintaining a stable dispersed state. Further, from the viewpoint of obtaining a sufficient deodorizing effect, it is preferably 99% by mass or less, more preferably 92% by mass or less.
〔その他の成分〕
本発明の消臭剤組成物には、成分(A)、(B)及び(C)に加えて、必要に応じて、多価アルコール、界面活性剤、成分(C)以外の溶剤、油剤、ゲル化剤、硫酸ナトリウムやN,N,N-トリメチルグリシン等の塩、pH調整剤、酸化防止剤、防腐剤、殺菌・抗菌剤、色素、紫外線吸収剤等の他の成分を添加することができる。
[Other ingredients]
In addition to the components (A), (B) and (C), the deodorant composition of the present invention contains, if necessary, a polyhydric alcohol, a surfactant, a solvent other than the component (C), an oil agent, and the like. Gelling agents, salts such as sodium sulfate and N, N, N-trimethylglycine, pH regulators, antioxidants, preservatives, bactericidal / antibacterial agents, pigments, UV absorbers and other other ingredients may be added. it can.
界面活性剤としては特に制限はなく、非イオン性界面活性剤、陽イオン性界面活性剤、両性界面活性剤及び陰イオン性界面活性剤から選ばれる１種以上が挙げられるが、非イオン性界面活性剤が好ましい。 The surfactant is not particularly limited, and examples thereof include one or more selected from nonionic surfactants, cationic surfactants, amphoteric surfactants and anionic surfactants, and nonionic surfactants. Activators are preferred.
溶剤としては、イソプロパノール等の炭素数３〜４のアルコール；エチレングリコール、プロピレングリコール、グリセリン、ソルビトール等の炭素数２〜12の多価アルコール；エチレングリコール、プロピレングリコール等のアルキレングリコールのモノエチル又はモノブチルエーテル；ジエチレングリコール、ジプロピレングリコール等のジアルキレングリコールのジエチル又はジブチルエーテル；ベンジルアルコール、ベンジルオキシエタノール等の芳香族アルコール；フェノール性化合物のエチレンオキシド又はプロピレンオキシド付加物等が挙げられるが、エチレングリコール、プロピレングリコール、グリセリン、ソルビトール等の炭素数２〜12の多価アルコール；ジエチレングリコール、ジプロピレングリコール等のジアルキレングリコールのジエチル又はジブチルエーテルが好ましい。 Examples of the solvent include alcohols having 3 to 4 carbon atoms such as isopropanol; polyhydric alcohols having 2 to 12 carbon atoms such as ethylene glycol, propylene glycol, glycerin and sorbitol; monoethyl or monobutyl ether of alkylene glycols such as ethylene glycol and propylene glycol. Dialkylene glycol diethyl or dibutyl ether such as diethylene glycol and dipropylene glycol; aromatic alcohols such as benzyl alcohol and benzyloxyethanol; ethylene oxide or propylene oxide adduct of phenolic compounds, etc., but ethylene glycol and propylene glycol. , Polyhydric alcohol having 2 to 12 carbon atoms such as glycerin and sorbitol; diethyl or dibutyl ether of dialkylene glycol such as diethylene glycol and dipropylene glycol is preferable.
本発明の消臭剤組成物の25℃におけるpHは、アルデヒド類に対する消臭効果の観点では特に制限はないが、皮膚刺激低減の観点から、好ましくは４以上、より好ましくは５以上であり、また、好ましくは10以下、より好ましくは８以下である。本発明の消臭剤組成物のpHは、リンゴ酸、クエン酸、コハク酸、フマル酸、乳酸、塩酸等の酸、又は水酸化ナトリウム等のアルカリを添加することにより調整することができる。 The pH of the deodorant composition of the present invention at 25 ° C. is not particularly limited from the viewpoint of the deodorizing effect on aldehydes, but is preferably 4 or more, more preferably 5 or more from the viewpoint of reducing skin irritation. Further, it is preferably 10 or less, more preferably 8 or less. The pH of the deodorant composition of the present invention can be adjusted by adding an acid such as malic acid, citric acid, succinic acid, fumaric acid, lactic acid or hydrochloric acid, or an alkali such as sodium hydroxide.
本発明の消臭剤組成物の使用形態に特に制限はなく、例えば、液状、ゲル状、ペースト状とすることができる。液状の場合には、特に洗浄剤として、人体、毛髪、ペット、繊維製品等に用いることができる。本発明の消臭剤組成物は、特に液体洗浄剤としてポンプタイプの容器に充填し、１回の吐出量を0.5〜２mLに調整したものが好ましい。また、ミストやスプレーとして用いる場合、衣類や空間に噴霧して広範囲を消臭するのに適している。 The form of use of the deodorant composition of the present invention is not particularly limited, and may be, for example, liquid, gel-like, or paste-like. When in liquid form, it can be used especially as a cleaning agent for the human body, hair, pets, textile products and the like. The deodorant composition of the present invention is particularly preferably filled in a pump-type container as a liquid cleaning agent and the amount discharged at one time is adjusted to 0.5 to 2 mL. When used as a mist or spray, it is suitable for spraying on clothes and spaces to deodorize a wide area.
試験例１（アルデヒド類の低減）
表１及び２に示す溶液Ａと溶液Ｂ（アルデヒド類として2-ノネナール又は2,4-デカジエナールを使用）からなるサンプルを調製し、溶液Ａと溶液Ｂを混合して30秒後及び60秒後における2-ノネナール及び2,4-デカジエナールの残存率を、GC/MSを用いて測定し成分(A)がアルデヒド類を即時的に低減する能力を確認した。結果を表中に併せて示す。
Test Example 1 (Reduction of aldehydes)
Prepare a sample consisting of solution A and solution B (using 2-nonenal or 2,4-decadienal as aldehydes) shown in Tables 1 and 2, and mix solution A and solution B 30 seconds and 60 seconds later. The residual rates of 2-nonenal and 2,4-decadienal were measured using GC / MS, and the ability of component (A) to immediately reduce aldehydes was confirmed. The results are also shown in the table.
上記結果より、プロリンは2-ノネナール及び2,4-デカジエナールを即時的に低減することができるとともに、低減効率が他のアミノ酸、アミン類と比較して高いことが確認された。また、上記結果より、プロリンによるアルデヒド類の低減速度及び低減効率はプロリン濃度に依存し、プロリンが低濃度の場合には十分な効果が発揮されないことが確認された。 From the above results, it was confirmed that proline can immediately reduce 2-nonenal and 2,4-decadienal, and its reduction efficiency is higher than that of other amino acids and amines. Further, from the above results, it was confirmed that the reduction rate and reduction efficiency of aldehydes by proline depend on the proline concentration, and a sufficient effect is not exhibited when the proline concentration is low.
試験例２（アルデヒド類のニオイの低減）
成分(A)を配合した消臭剤組成物を製品形態で実際に使用した際におけるアルデヒド由来のニオイの低減効果を確認するため、表３のサンプル15〜17に示したモデル洗浄剤を用いて、手についた2-ノネナール臭、及び2,4-デカジエナール臭の洗浄によるニオイ落ち試験を実施した。
被検者の指に、ジプロピレングリコールで20mMに希釈した2-ノネナール又は2,4-デカジエナールを50μL塗布して１分間静置し、２秒間水洗した後、モデル洗浄剤又はこれにプロリンを含有させた洗浄剤を用いて洗浄（洗浄剤を0.5g塗布して30秒マッサージし、10秒間水洗）した。
悪臭化合物塗布時、水洗後、洗浄剤による洗浄後の３段階における2-ノネナール臭又は2,4-デカジエナール臭の強さについて、専門パネラー（３名）による官能評価を行った。官能評価は、以下の６段階で行い、３名の協議により評価した。結果を表３に併せて示す。なお、評価は、悪臭化合物塗布時の臭いの強さを５、悪臭化合物無しの臭いを０とし、以下に示す６段階で行った。
０：無臭
１：ごくわずかに感じる
２：弱く感じる
３：はっきりと感じる
４：強く感じる
５：かなり強く感じる
Test Example 2 (Reduction of aldehyde odor)
In order to confirm the effect of reducing aldehyde-derived odor when the deodorant composition containing the component (A) is actually used in the product form, the model cleaning agents shown in Samples 15 to 17 in Table 3 were used. , A odor removal test was carried out by cleaning the 2-nonenal odor and the 2,4-decadienal odor on the hands.
50 μL of 2-nonenal or 2,4-decadienal diluted to 20 mM with dipropylene glycol was applied to the subject's finger, allowed to stand for 1 minute, washed with water for 2 seconds, and then containing a model cleaning agent or proline. Cleaning was performed using the cleaning agent (0.5 g of the cleaning agent was applied, massaged for 30 seconds, and washed with water for 10 seconds).
Sensory evaluation was performed by expert panelists (3 persons) on the strength of 2-nonenal odor or 2,4-decadienal odor in three stages after application of the malodorous compound, washing with water, and washing with a cleaning agent. The sensory evaluation was performed in the following 6 stages, and was evaluated by consultation of 3 people. The results are also shown in Table 3. The evaluation was carried out in the following 6 steps, with the intensity of the odor when the malodorous compound was applied being 5 and the odor without the malodorous compound being 0.
0: Odorless 1: Very slightly felt 2: Weakly felt 3: Clearly felt 4: Strongly felt 5: Very strong
上記結果より、プロリンを配合した洗浄剤は、プロリンを配合していない洗浄剤よりも2-ノネナール臭及び2,4-デカジエナール臭を低減する効果が高いことがわかった。このことから、成分(A)によるアルデヒド類の即時的な低減効果が、製品形態で実際に使用した際にも有効であることを確認した。 From the above results, it was found that the cleaning agent containing proline is more effective in reducing the 2-nonenal odor and the 2,4-decadienal odor than the cleaning agent not containing proline. From this, it was confirmed that the immediate reduction effect of aldehydes by the component (A) is effective even when it is actually used in the product form.
試験例３（アミノ酸とシトラールの併用による着色）
成分(A)が香料の着色に与える影響を調べるため、成分(b-1-1)に相当する香料化合物であるシトラールについて、プロリン又は代表的なアミノ酸を含む溶液中における着色を観察した。シトラールの希釈品３mLをスクリュー管（マルエム社製、スクリュー管瓶、No3）に入れ、アミノ酸を添加した後の液色の経時変化を記録した。白地背景で溶液色をデジタル撮影し、パソコンへ取り込み、Microsoft ペイント（Windows10）を用いて溶液色のRGB値を取得し、Development of a Generic RGB to HSV Hardware（DOI: 10.12792/iciae2013.034）に記載された方法に従ってHSV値に変換した。全てのサンプルのHSV値から、黄系統の液色を呈したものについては色相55、明度100のカラースケール（表４）、橙系統の液色を呈したものについては色相40、明度100のカラースケール（表５）を用いることで、溶液色を統一的に比較できると判断した。撮影した各液色画像について、表４及び表５のカラースケールの中から最も近い色の彩度を、溶液色の観察結果として記録した。結果を表６に示す。
Test Example 3 (Coloring by combined use of amino acids and citral)
In order to investigate the effect of component (A) on the coloring of fragrances, citral, which is a fragrance compound corresponding to component (b-1-1), was observed to be colored in a solution containing proline or a typical amino acid. 3 mL of diluted citral was placed in a screw tube (Maruem Co., Ltd., screw tube bottle, No. 3), and the change in liquid color over time after adding amino acids was recorded. Digitally photograph the solution color on a white background, import it to a personal computer, acquire the RGB value of the solution color using Microsoft Paint (Windows10), and describe it in the Development of a Generic RGB to HSV Hardware (DOI: 10.12792 / iciae2013.034). Converted to HSV value according to the method described. From the HSV values of all the samples, the color scale of hue 55 and lightness 100 for those with yellowish liquid color (Table 4), and the color of hue 40 and lightness 100 for those with orange liquid color. It was judged that the solution colors could be compared in a unified manner by using the scale (Table 5). For each liquid color image taken, the saturation of the color closest to the color scales in Tables 4 and 5 was recorded as the observation result of the solution color. The results are shown in Table 6.
上記結果より、プロリン溶液中では、他のアミノ酸溶液中と比較して短時間のうちにシトラールが著しく呈色することが確認された。このことから、プロリンは香料と併用した際の着色リスクがアミノ酸類の中で特に高いことが明らかとなった。 From the above results, it was confirmed that citral was remarkably colored in the proline solution in a short time as compared with other amino acid solutions. From this, it was clarified that proline has a particularly high risk of coloring when used in combination with a fragrance among amino acids.
試験例４
成分(A)による香料の着色における成分(A)の濃度の影響を調べるため、プロリン及びシトラールをモデル洗浄剤（表３のサンプル15）に配合して表７に示す溶液を調製し、その液色変化を観察した。調製した洗浄剤の色を表４、表５のカラースケールと目視にて比較し、溶液の色の彩度を記録した。この結果を表７に併せて示す
Test Example 4
In order to investigate the effect of the concentration of the component (A) on the coloring of the fragrance by the component (A), proline and citral were mixed with a model cleaning agent (Sample 15 in Table 3) to prepare the solution shown in Table 7, and the solution was prepared. The color change was observed. The colors of the prepared cleaning agents were visually compared with the color scales of Tables 4 and 5, and the color saturation of the solution was recorded. The results are also shown in Table 7.
上記結果より、洗浄剤の着色速度及び呈色の度合いは、配合されたプロリン濃度に依存的であり、プロリンを高濃度に配合した消臭剤組成物では、香料による着色リスクが著しく高まることを確認した。 From the above results, it can be seen that the coloring rate and the degree of color development of the cleaning agent depend on the concentration of the blended proline, and the deodorant composition containing a high concentration of proline significantly increases the risk of coloring due to the fragrance. confirmed.
実施例１〜４、比較例１〜３
成分(A)を高濃度で配合した消臭剤組成物について、配合した香料種による着色挙動及び悪臭の低減能の違いを確認するため、表８に示す消臭剤組成物（溶液Ａ）を調製、保存した際の溶液色を、表４及び表５のカラースケールと目視にて比較し、溶液の色の彩度を記録するとともに、消臭剤組成物（溶液Ａ）と2-ノネナールのエタノール溶液（溶液Ｂ）を混合し、30秒後及び60秒後の2-ノネナールの残存率をGC/MSを用いて測定した。この結果を表９に示す。
Examples 1-4, Comparative Examples 1-3
For the deodorant composition containing the component (A) at a high concentration, the deodorant composition (solution A) shown in Table 8 was used to confirm the difference in coloring behavior and malodor reduction ability depending on the blended fragrance type. The color of the solution when prepared and stored was visually compared with the color scales of Tables 4 and 5, and the color saturation of the solution was recorded, and the deodorant composition (solution A) and 2-nonenal were recorded. The ethanol solution (solution B) was mixed, and the residual rate of 2-nonenal after 30 seconds and 60 seconds was measured using GC / MS. The results are shown in Table 9.
上記結果より、添加する香料素材の種類及び量を適切に選択、制御した消臭剤組成物では、香料による着色を生じることなく、アルデヒド悪臭を即時的に低減できることが確認された。 From the above results, it was confirmed that the deodorant composition in which the type and amount of the fragrance material to be added was appropriately selected and controlled could immediately reduce the aldehyde malodor without causing coloring by the fragrance.
実施例５〜16、比較例４〜９
成分(A)を高濃度で配合した消臭剤組成物について、適切な香料の選定による着色対策の有効性を確認するため、表10に示す着色検証用溶液、又は表３のサンプル15に示すモデル洗浄剤とプロリン2.5ｇの混合液に、検証用香料（計1.0質量％）を配合して表11に示す溶液を調製し、着色の有無を確認した。各溶液3mLをスクリュー管（マルエム社製、スクリュー管瓶、No3）に入れ、アミン類を添加した後の液色の経時変化を記録した。白地背景で溶液色をデジタル撮影し、パソコンへ取り込み、Microsoft ペイント（Windows10）を用いて溶液色のRGB値を取得し、Development of a Generic RGB to HSV Hardware（DOI: 10.12792/iciae2013.034）に記載された方法に従ってHSV値に変換した。全てのサンプルのHSV値から、黄系統の液色を呈したものについては色相55、明度100のカラースケール（表４）、橙系統の液色を呈したものについては色相40、明度100のカラースケール（表５）を用いることで、溶液色を統一的に比較できると判断した。撮影した各液色画像について、表４及び表５のカラースケールの中から最も近い色の彩度を、溶液色の観察結果として記録した。結果を表11に示す。
Examples 5-16, Comparative Examples 4-9
In order to confirm the effectiveness of anti-coloring measures by selecting an appropriate fragrance for the deodorant composition containing the component (A) at a high concentration, the solution for color verification shown in Table 10 or sample 15 in Table 3 is shown. A verification fragrance (1.0% by mass in total) was mixed with a mixed solution of a model cleaning agent and 2.5 g of proline to prepare a solution shown in Table 11, and the presence or absence of coloring was confirmed. 3 mL of each solution was placed in a screw tube (Maruem Co., Ltd., screw tube bottle, No. 3), and the change in liquid color with time after addition of amines was recorded. Digitally photograph the solution color on a white background, import it to a personal computer, acquire the RGB value of the solution color using Microsoft Paint (Windows10), and describe it in the Development of a Generic RGB to HSV Hardware (DOI: 10.12792 / iciae2013.034). Converted to HSV value according to the method described. From the HSV values of all the samples, the color scale of hue 55 and lightness 100 for those with yellowish liquid color (Table 4), and the color of hue 40 and lightness 100 for those with orange liquid color. It was judged that the solution colors could be compared in a unified manner by using the scale (Table 5). For each liquid color image taken, the saturation of the color closest to the color scales in Tables 4 and 5 was recorded as the observation result of the solution color. The results are shown in Table 11.
上記結果より、実施例５〜16の消臭剤組成物では配合後１ヵ月が経過しても着色しなかったのに対し、比較例４〜９の消臭剤組成物では配合３日〜１週間後に着色が認められた。このことから、添加する香料素材の種類及び量を適切に選択、制御し、成分(b-1)と成分(b-2)の含有質量比(b-1)／(b-2)を適切に調整することにより、プロリンを配合した消臭剤組成物の香料による着色を防ぐことができることを確認した。 From the above results, the deodorant compositions of Examples 5 to 16 did not color even one month after compounding, whereas the deodorant compositions of Comparative Examples 4 to 9 were compounded 3 days to 1 day. Coloring was observed after a week. From this, the type and amount of the fragrance material to be added are appropriately selected and controlled, and the content mass ratio (b-1) / (b-2) of the component (b-1) and the component (b-2) is appropriate. It was confirmed that the deodorant composition containing proline could be prevented from being colored by the fragrance.
実施例17〜22、比較例10〜12
成分(A)と香料を配合した消臭剤組成物を実際に使用した際の消臭効果を確認するため、表12に示す洗浄剤組成物を調製し、手についた2-ノネナール臭、及び2,4-デカジエナール臭の洗浄によるニオイ落ち試験を実施した。
被検者の指に、ジプロピレングリコールで20mMに希釈した2-ノネナール又は2,4-デカジエナールを50μL塗布して１分間静置し、２秒間水洗した後、洗浄剤組成物を用いて洗浄（洗浄剤を0.5g塗布して30秒マッサージし、10秒間水洗）した。
悪臭化合物塗布時、水洗後、モデル洗浄剤による洗浄後の３段階における2-ノネナール臭又は2,4-デカジエナール臭の強さについて、専門パネラー（３名）による官能評価を行った。官能評価は、以下の６段階で行い、３名の協議により評価した。結果を表13、表14に示す。なお、評価は、悪臭化合物塗布時の臭いの強さを５、悪臭化合物無しの臭いを０とし、以下に示す６段階で行った。
０：無臭
１：ごくわずかに感じる
２：弱く感じる
３：はっきりと感じる
４：強く感じる
５：かなり強く感じる
Examples 17-22, Comparative Examples 10-12
In order to confirm the deodorizing effect when the deodorant composition containing the component (A) and the fragrance was actually used, the cleaning agent composition shown in Table 12 was prepared, and the 2-nonenal odor and the 2-nonenal odor on the hands and the hand were prepared. A odor removal test was conducted by cleaning the 2,4-decadienal odor.
Apply 50 μL of 2-nonenal or 2,4-decadienal diluted to 20 mM with dipropylene glycol to the subject's finger, let stand for 1 minute, wash with water for 2 seconds, and then wash with a cleaning agent composition ( 0.5 g of cleaning agent was applied, massaged for 30 seconds, and washed with water for 10 seconds).
Sensory evaluation was performed by expert panelists (3 persons) on the strength of 2-nonenal odor or 2,4-decadienal odor in three stages after application of the malodorous compound, washing with water, and washing with a model cleaning agent. The sensory evaluation was performed in the following 6 stages, and was evaluated by consultation of 3 people. The results are shown in Tables 13 and 14. The evaluation was carried out in the following 6 steps, with the intensity of the odor when the malodorous compound was applied being 5 and the odor without the malodorous compound being 0.
0: Odorless 1: Very slightly felt 2: Weakly felt 3: Clearly felt 4: Strongly felt 5: Very strong
上記結果より、プロリン配合による消臭剤組成物の消臭性能の向上は、香料を併用した場合にも認められることが確認された。 From the above results, it was confirmed that the improvement of the deodorizing performance of the deodorant composition by the addition of proline was observed even when the fragrance was used in combination.
また、各消臭剤組成物の調製、保存後における配合直後から配合１ヶ月後までの溶液の色について、前記と同様に表４及び表５のカラースケールとの比較による評価を行ったが、全て（実施例、比較例とも）、彩度は０であった。 In addition, the color of the solution after preparation and storage of each deodorant composition from immediately after compounding to 1 month after compounding was evaluated by comparison with the color scales of Tables 4 and 5 in the same manner as described above. In all (both examples and comparative examples), the saturation was 0.
試験例５（消臭剤自身のニオイ）
消臭成分が消臭剤組成物そのもののニオイに与える影響を調べるため、プロリン水溶液の官能評価を行った。比較例としてアルギニン、システインの水溶液を評価した。調製した水溶液をバイアルに入れ、男性５名、女性５名、計10名のパネラーに溶液の臭いを嗅いでもらい、溶液の臭いの不快度を以下の４段階で評価し、その平均値を求めた。なお、評価は、システイン300mM水溶液の臭いの強さを３、ブランク（水）の臭いを０とし、以下に示す４段階で行った。
０：全く不快に感じない
１：あまり不快に感じない
２：やや不快に感じる
３：不快に感じる
評価は平均値１未満が好ましい。平均値１以上では、当該濃度で消臭剤組成物に配合した際に不快なニオイを呈し、使用感に悪影響を与える。この結果を表15に示す。
Test Example 5 (Odor of deodorant itself)
In order to investigate the effect of the deodorant component on the odor of the deodorant composition itself, a sensory evaluation of the aqueous proline solution was performed. As a comparative example, an aqueous solution of arginine and cysteine was evaluated. The prepared aqueous solution was placed in a vial, and a total of 10 panelists, 5 males and 5 females, were asked to smell the solution, and the discomfort of the solution odor was evaluated in the following 4 stages, and the average value was calculated. It was. The evaluation was carried out in the following four steps, with the odor intensity of the cysteine 300 mM aqueous solution being 3 and the odor of the blank (water) being 0.
0: I do not feel uncomfortable at all 1: I do not feel very uncomfortable 2: I feel a little uncomfortable 3: I feel uncomfortable The average evaluation is preferably less than 1. If the average value is 1 or more, an unpleasant odor is exhibited when the deodorant composition is blended at the concentration, which adversely affects the usability. The results are shown in Table 15.
上記結果より、システインは15mM以上、アルギニンは50mM以上の濃度で、配合液が不快なニオイを呈するのに対し、プロリンについては、300mM（3.45質量％）の濃度でも配合液が不快なニオイを呈することはなかった。 From the above results, the compound solution exhibits an unpleasant odor at a concentration of 15 mM or more for cysteine and 50 mM or more for arginine, whereas the compound solution exhibits an unpleasant odor even at a concentration of 300 mM (3.45% by mass) for proline. It never happened.
実際の消臭剤組成物における消臭成分のニオイの影響を確認するため、表３におけるサンプル15の消臭剤組成物に各種アミノ酸を添加して官能評価を行ったところ、システインを15mMの濃度で配合した消臭剤組成物が不快な硫黄臭を呈したのに対し、プロリンについては、300mM（3.45質量％）の濃度で配合した場合にも、消臭剤組成物が不快なニオイを呈することはなく、問題なく使用することができた。 In order to confirm the effect of odor of the deodorant component on the actual deodorant composition, various amino acids were added to the deodorant composition of sample 15 in Table 3 and sensory evaluation was performed. As a result, cysteine had a concentration of 15 mM. While the deodorant composition blended in 1 exhibited an unpleasant sulfur odor, the deodorant composition exhibited an unpleasant odor even when blended at a concentration of 300 mM (3.45% by mass) for proline. There was no problem and I was able to use it without any problems.
処方例１〜５
本発明における成分(A)と成分(b-1)の含有質量比(b-1)／(A)、及び成分(b-1)と成分(b-2)の含有質量比(b-1)／(b-2)の条件を満たした好適な消臭剤組成物の処方例を、表16-1〜表16-2に示す。
Prescription Examples 1-5
The content mass ratio (b-1) / (A) of the component (A) and the component (b-1) in the present invention, and the content mass ratio (b-1) of the component (b-1) and the component (b-2). ) / (B-2) are shown in Tables 16-1 to 16-2.
Claims (6)
成分(A)：下記一般式(1)で表される複素環式化合物又はその塩
成分(B)：下記成分(b-1)と成分(b-2)との含有質量比(b-1)／(b-2)が１／６以下である香料組成物
成分(b-1)：炭素数６〜18のα,β-不飽和カルボニル香料化合物
成分(b-2)：成分(b-1)に該当しない香料化合物
成分(C)：水及びエタノールから選択される１種以上
を含有し、成分(A)の含有量が0.2質量％以上６質量％以下であり、成分(B)の含有量が0.01質量％以上1.4質量％以下である、消臭剤組成物。 The following components (A) to (C);
Component (A): Heterocyclic compound represented by the following general formula (1) or a salt thereof
Component (B): Perfume composition component (b-1) in which the content mass ratio (b-1) / (b-2) of the following component (b-1) and component (b-2) is 1/6 or less. ): Α, β-unsaturated carbonyl fragrance compound having 6 to 18 carbon mass Component (b-2): Fragrance compound not corresponding to component (b-1) Component (C): One or more selected from water and ethanol A deodorant composition containing 0.2% by mass or more and 6% by mass or less of the component (A) and 0.01% by mass or more and 1.4% by mass or less of the content of the component (B).
成分(b-2-1)：α,β-不飽和アルデヒドに該当しないアルデヒド
成分(b-2-2)：α,β-不飽和ケトンに該当しないケトン
成分(b-2-3)：アルデヒド及びケトンに該当しないアルコール、エステル、エーテル又は炭化水素 Any one of claims 1 to 3, wherein the component (b-2) is at least one selected from the components (b-2-1), (b-2-2) and (b-2-3). The deodorant composition according to the item.
Component (b-2-1): Aldehyde not corresponding to α, β-unsaturated aldehyde Component (b-2-2): Ketone component not corresponding to α, β-unsaturated ketone (b-2-3): Aldehyde And alcohols, esters, ethers or hydrocarbons that do not correspond to ketones
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