DE3009543A1 - Deodorant cosmetic compsn. e.g. sprays and sticks - contg. alpha-branched alkanoic acid derivs. and opt. antioxidant - Google Patents
Deodorant cosmetic compsn. e.g. sprays and sticks - contg. alpha-branched alkanoic acid derivs. and opt. antioxidantInfo
- Publication number
- DE3009543A1 DE3009543A1 DE19803009543 DE3009543A DE3009543A1 DE 3009543 A1 DE3009543 A1 DE 3009543A1 DE 19803009543 DE19803009543 DE 19803009543 DE 3009543 A DE3009543 A DE 3009543A DE 3009543 A1 DE3009543 A1 DE 3009543A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- carbon atoms
- product
- radical
- derivatives
- 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.)
- Withdrawn
Links
- 239000002253 acid Substances 0.000 title claims abstract description 21
- 239000002537 cosmetic Substances 0.000 title claims abstract description 19
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 6
- 239000002781 deodorant agent Substances 0.000 title claims description 29
- 239000007921 spray Substances 0.000 title abstract description 7
- 230000003078 antioxidant effect Effects 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 18
- 150000007513 acids Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- -1 sticks Substances 0.000 abstract description 15
- 230000000694 effects Effects 0.000 abstract description 5
- 235000006708 antioxidants Nutrition 0.000 abstract description 4
- 239000000843 powder Substances 0.000 abstract description 4
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 206010040904 Skin odour abnormal Diseases 0.000 abstract description 2
- 239000006071 cream Substances 0.000 abstract description 2
- 150000002825 nitriles Chemical class 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000009835 boiling Methods 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000001877 deodorizing effect Effects 0.000 description 5
- 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 4
- 230000000845 anti-microbial effect Effects 0.000 description 4
- 230000001166 anti-perspirative effect Effects 0.000 description 4
- 239000003213 antiperspirant Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 4
- 239000003380 propellant Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 210000004243 sweat Anatomy 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 2
- IANSAVNPGVTFKQ-UHFFFAOYSA-N 2-(diethylcarbamoyl)-2-ethylbutanoic acid Chemical compound CCN(CC)C(=O)C(CC)(CC)C(O)=O IANSAVNPGVTFKQ-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 206010040880 Skin irritation Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 2
- SXIUQXQCWYCRQZ-UHFFFAOYSA-N hexyl 2-ethylbutanoate Chemical compound CCCCCCOC(=O)C(CC)CC SXIUQXQCWYCRQZ-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229940047889 isobutyramide Drugs 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LYGCLXFQIQORSE-UHFFFAOYSA-N n,n,2-triethylhexanamide Chemical compound CCCCC(CC)C(=O)N(CC)CC LYGCLXFQIQORSE-UHFFFAOYSA-N 0.000 description 2
- PAUJKVQAWLQVGZ-UHFFFAOYSA-N n-butyl-2-ethylhexanamide Chemical compound CCCCNC(=O)C(CC)CCCC PAUJKVQAWLQVGZ-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 150000003140 primary amides Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000036556 skin irritation Effects 0.000 description 2
- 231100000475 skin irritation Toxicity 0.000 description 2
- 244000005714 skin microbiome Species 0.000 description 2
- SKHXHUZZFVMERR-UHFFFAOYSA-N 1-Isopropyl citrate Chemical compound CC(C)OC(=O)CC(O)(C(O)=O)CC(O)=O SKHXHUZZFVMERR-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- KICJYSRARHIXHM-UHFFFAOYSA-N 2,2-dimethyloctanoyl chloride Chemical compound CCCCCCC(C)(C)C(Cl)=O KICJYSRARHIXHM-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- WJNJRMDHLZDCJH-UHFFFAOYSA-N 2-ethyl-1-morpholin-4-ylhexan-1-one Chemical compound CCCCC(CC)C(=O)N1CCOCC1 WJNJRMDHLZDCJH-UHFFFAOYSA-N 0.000 description 1
- SDKATVAEMVYSAB-UHFFFAOYSA-N 2-ethyl-dodecanoic acid Chemical compound CCCCCCCCCCC(CC)C(O)=O SDKATVAEMVYSAB-UHFFFAOYSA-N 0.000 description 1
- WBGFYNHGMLQKAA-UHFFFAOYSA-N 2-ethyl-n,n-dihexylbutanamide Chemical compound CCCCCCN(C(=O)C(CC)CC)CCCCCC WBGFYNHGMLQKAA-UHFFFAOYSA-N 0.000 description 1
- YTPZZUAPUOFFID-UHFFFAOYSA-N 2-ethyl-n,n-dipropylhexanamide Chemical compound CCCCC(CC)C(=O)N(CCC)CCC YTPZZUAPUOFFID-UHFFFAOYSA-N 0.000 description 1
- NXLBBKQIOWRQOU-UHFFFAOYSA-N 2-ethyl-n-(2-ethylhexyl)hexanamide Chemical compound CCCCC(CC)CNC(=O)C(CC)CCCC NXLBBKQIOWRQOU-UHFFFAOYSA-N 0.000 description 1
- LXAXZDMBYCYMCO-UHFFFAOYSA-N 2-ethyl-n-octylhexanamide Chemical compound CCCCCCCCNC(=O)C(CC)CCCC LXAXZDMBYCYMCO-UHFFFAOYSA-N 0.000 description 1
- WJZIPMQUKSTHLV-UHFFFAOYSA-N 2-ethyldecanoic acid Chemical compound CCCCCCCCC(CC)C(O)=O WJZIPMQUKSTHLV-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 1
- GWXXFGWOWOJEEX-UHFFFAOYSA-N 4,4,4-trihydroxy-1-phenylbutan-1-one Chemical compound OC(CCC(=O)C1=CC=CC=C1)(O)O GWXXFGWOWOJEEX-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000035985 Body Odor Diseases 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 241001440269 Cutina Species 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 1
- RPWFJAMTCNSJKK-UHFFFAOYSA-N Dodecyl gallate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 RPWFJAMTCNSJKK-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004263 Guaiac resin Substances 0.000 description 1
- 229920000932 Gum guaicum Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
- VVBSJLOOLIEZEF-UHFFFAOYSA-N N,N-diethyl-2,2-dimethyloctanamide Chemical compound CCN(C(C(C)(C)CCCCCC)=O)CC VVBSJLOOLIEZEF-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000003490 Thiodipropionic acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- IOHCODIDWIYZGP-UHFFFAOYSA-N decyl 2-ethylbutanoate Chemical compound CCCCCCCCCCOC(=O)C(CC)CC IOHCODIDWIYZGP-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 1
- 239000000555 dodecyl gallate Substances 0.000 description 1
- 235000010386 dodecyl gallate Nutrition 0.000 description 1
- 229940080643 dodecyl gallate Drugs 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 235000019278 guaiac resin Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KLVRKNJSKXACLQ-UHFFFAOYSA-N n,n,2-triethylbutanamide Chemical compound CCC(CC)C(=O)N(CC)CC KLVRKNJSKXACLQ-UHFFFAOYSA-N 0.000 description 1
- TXPXZGIYPUUXMV-UHFFFAOYSA-N n,n-dibutyl-2-ethylbutanamide Chemical compound CCCCN(CCCC)C(=O)C(CC)CC TXPXZGIYPUUXMV-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- HCZKYJDFEPMADG-UHFFFAOYSA-N nordihydroguaiaretic acid Chemical compound C=1C=C(O)C(O)=CC=1CC(C)C(C)CC1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000000574 octyl gallate Substances 0.000 description 1
- 235000010387 octyl gallate Nutrition 0.000 description 1
- NRPKURNSADTHLJ-UHFFFAOYSA-N octyl gallate Chemical compound CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 NRPKURNSADTHLJ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- COLWXZYBIQYHDB-UHFFFAOYSA-N prop-2-enyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC=C COLWXZYBIQYHDB-UHFFFAOYSA-N 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011787 zinc oxide 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
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
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- Life Sciences & Earth Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Abstract
Description
"Desodorierende kosmetische Zusammensetzungen""Deodorant cosmetic compositions"
Die Erfindung betriefft desodorierende kosmetische Zusammensetzungen mit einem Gehalt an Derivaten -verzweigter Alkansäuren.The invention relates to deodorant cosmetic compositions with a content of derivatives -branched alkanoic acids.
Es ist bekannt, daß der störende Geruch, der die Perspiration des Menschen begleitet, durch die bakterielle Zersetzung des zunächst geruchlosen Schweißes verursacht wird. Es hat daher nicht an Vorschlägen gefehlt, diesem jübelstand zu begegnen, ohne daß es bisher zu einer alseits befriedigenden Lösung gekommen wäre. Im wesentlichten handelt es sich um zwei Wege, die zur Lösung des Problems eingeschlagen wurden, einmal um den Einsatz antimikrobieller Verbindungen zur Abtötung beziehungsi weise Wachstumshemmung der bakteriellen Hautflora, die die Zersetzung des Schweißes verursacht, zum anderen um den Einsatz von Verbindungen, die die Schweißabsonderung unterbinden. Daneben spielen noch rein sorptiv wirkende sowie geruchsüberdeckende Mittel eine völlig untergeordnete Rolle. Sowohl der Einsatz der die Schweißabsonderung unterbindenden Antitranspirantien als auch der antii mikrobiellen Verbindungen ist umstritten, da im ersten Fall ein Eingriff in den physiologischen Vorgang der Schweißbildung erfolgt, was unerwünscht ist und im zweiten Fall neben der Wachstumshemmung der die Schweißzersetzung bewirkenden Bakterien auch ein Eingriff in die natürliche Hautflora erfolgt. Darüber hinaus kann der längere Gebrauch von Antitranspirantien zu Hautreizungen und zu Hautveränderungen führen. Bei den kosmetischen Mitteln mit desodorierender Wirkung handelt es sich durchweg um Mittel mit einem Gehalt an antimikrobiellen Stoffen.It is known that the unpleasant smell which the perspiration of the People are accompanied by the bacterial decomposition of the initially odorless sweat caused. There has therefore been no lack of proposals to approve this jübelstand meet without a satisfactory solution as yet having come about. Essentially there are two ways in which to solve the problem were once around the use of antimicrobial compounds to kill relationships wise growth inhibition of the bacterial skin flora, which causes the decomposition of sweat caused, on the other hand, to the use of compounds that reduce perspiration prevent. In addition, purely sorptive and odor-masking effects also play a role Means a completely subordinate role. Both the use of the perspiration antiperspirants as well as anti-microbial compounds controversial because in the first case it interferes with the physiological process of perspiration occurs, which is undesirable and in the second case in addition to the inhibition of growth The bacteria causing the decomposition of sweat also interfere with the natural Skin flora takes place. In addition, prolonged use of antiperspirants can result cause skin irritation and skin changes. In the cosmetic products with deodorizing effect is consistently about Means with one Antimicrobial content.
Als solche werden zum Beispiel Phenolderivate mit und ohne Halogensubstituenten, quartäre Ammoniumverbindungen, ; desinfizierend wirkende Abkömmlinge von Aminosäuren vorgeschlagen. Wenn bei dem Einsatz der Deodorantien die Gefahr von Hautreizungen nicht in so hohem Maße wie bei der Verwendung von Antitranspirantien heraufbeschworen wird, so treten auch bei der laufenden Benutzung von Antimikrobika enthaltenden Deodorantien neben der Schädi-, ging der haut eigenen Flora gelegentliche Unverträglichkeiten, Lichtsensibilisierungen und toxische Nebeni wirkungen unterschiedlicher Stärke auf. Darüber hinaus ist die Mehrzahl dieser Produkte nicht geruchlos, manche besitzen einen leicht phenolischen Geruch, der bei vielen Benutzern auf Ablehnung stößt. Man ist daher weiterhin bestrebt, sehr gut desodorierende, von Nebenwirkungen , weitgehend freie kosmetische Mittel zur Unterdrückung von Körpergeruch herzustellen. As such, for example, phenol derivatives with and without halogen substituents, quaternary ammonium compounds,; Disinfecting derivatives of amino acids suggested. When using deodorants there is a risk of skin irritation not as high as evoked with the use of antiperspirants will occur even with ongoing use of antimicrobials containing Deodorants in addition to the harmful, the skin's own flora went occasional intolerances, Light sensitizations and toxic side effects of varying strength. In addition, the majority of these products are not odorless, some possess a slightly phenolic odor that many users dislike. The aim is therefore to continue to deodorize very well, to avoid side effects, Manufacture largely free cosmetic agents for suppressing body odor.
Es wurde nun gefunden, daß desodorierende kosmetische Zusammensetzungen mit einem Gehalt an Derivaten a-verzweigter Alkansäuren der allgemeinen Formel in der R1 für einen geradkettigen Alkylrest mit l - 12 Kohlenstoffat omen oder den Rest R2 für einen geradkettigen Alkylrest mit l - 6 Kohlenstoffatomen, R3 für ein Wasserstoffatom oder einen geradkettigen Alkylrest mit 1 - 6 Kohlenstoffatomen, X für Sauerstoff, Y für -OH, -OR4, -NR5R6, wobei R4 einen Alkylrest mit 1 - 10 Kohlenstoffatomen oder einen Aralkylrest und R5 und R6 unabhängig voneinander Wasserstoff, einen Alkylrest mit 1 - 12 Kohlenstoffatomen, einen Hydroxyalkylrest mit 2 - 4 Kohlenstoffatomen, einen Alkoxyalkylrest, einen Aryl- oder Aralkylrest bedeuten oder zusammen mit dem Stickstoffatom einen heterocyclischen Ring bilden, beziehungsweise auch für eine Nitrilgruppe stehen, die gestellten Anforderungen weitgehend erfüllen.It has now been found that deodorant cosmetic compositions containing derivatives of α-branched alkanoic acids of the general formula in which R1 stands for a straight-chain alkyl radical with 1-12 carbon atoms or the remainder R2 for a straight-chain alkyl radical with 1-6 carbon atoms, R3 for a hydrogen atom or a straight-chain alkyl radical with 1-6 carbon atoms, X for oxygen, Y for -OH, -OR4, -NR5R6, where R4 is an alkyl radical with 1-10 carbon atoms or an aralkyl radical and R5 and R6 independently of one another are hydrogen, an alkyl radical with 1-12 carbon atoms, a hydroxyalkyl radical with 2-4 carbon atoms, an alkoxyalkyl radical, an aryl or aralkyl radical or together with the nitrogen atom form a heterocyclic ring, respectively also stand for a nitrile group, largely meet the requirements.
Die Herstellung der erfindungsgemäß einzusetzenden Derivate a-verzweigter Alkansäuren erfolgt nach allgemein bekannten Verfahren der organischen Synthese, zum Beispiel der Ester durch Reaktion der Alkansäuren mit den entsprechenden Alkoholen in Gegenwart von SchweSelsSure, der Amide vorteilhaft über die entsprechenden Säurechloride und der Nitrile durch Dehydratisierung der primären Amide.The preparation of the α-branched derivatives to be used according to the invention Alkanoic acids are carried out according to generally known methods of organic synthesis, for example the esters by reaction of the alkanoic acids with the corresponding alcohols in the presence of sulfuric acid, the amides are advantageous over the corresponding acid chlorides and the nitriles by dehydrating the primary amides.
Als den erfindungsgemäß einzusetzenden Derivaten a-verzweigter Alkansäuren zugrunde liegende Carbonsäuren sind zum Beispiel Isobuttersäure, Pivalinsäure5 2-Methyl-, 2-Ethyl-buttersäure, 2-Methyl-, 2,2-Dimethyl-v2leriansäure, 2-Methyl-, 2,2-Dimethyl-, 2-Ethyl-caprinsäure, 2-Ethyl-laurinsEure anzuführen.As the derivatives of α-branched alkanoic acids to be used according to the invention underlying carboxylic acids are, for example, isobutyric acid, pivalic acid5 2-methyl-, 2-ethyl-butyric acid, 2-methyl-, 2,2-dimethyl-v2leric acid, 2-methyl-, 2,2-dimethyl-, 2-ethyl-capric acid, 2-ethyl-lauric acid.
Als Alkylreste der alkoholischen Komponente der erfindungsgemäß einzusetzenden Esterderivate a-verzweigter Alkansäuren sind z.B. der Methyl-, Ethyl-, Propyl-, Isopropyl-, n-Butyl-, iso-Butyl-, sek. Butyl-, tert.As alkyl radicals of the alcoholic component those to be used according to the invention Ester derivatives of a-branched alkanoic acids are e.g. methyl, ethyl, propyl, Isopropyl, n-butyl, iso-butyl, sec. Butyl, tert.
Butyl-, Pentyl-, Hexyl-, Octyl- und Decylrest zu nennen.Butyl, pentyl, hexyl, octyl and decyl radicals.
Als Amidkomponente kommen neben primären Amiden zum Beispiel Methyl-, Dimethyl-, Ethyl-, Diethyl-, Propyl-, Dipropyl-, Methglpropyl-, 2-Propyl-, Di-2-propyl-, Butyl-5 Dibutyl-, sek. Butyl-, tert.In addition to primary amides, methyl, Dimethyl, ethyl, diethyl, propyl, dipropyl, methglpropyl, 2-propyl, di-2-propyl, Butyl-5 dibutyl, sec. Butyl, tert.
Butyl-, Hexyl-, Dihexyl-, 2-Ethyl-hexyl-, Octyl-, Ethyloctyl-, Decyl-, Dodecyl-, Ethanol-, Diisopropanol-, 3-Methoxypropyl-, 3- ( 2-Ethylhexoxy) -propyl-, Benzylamid, Anilid, N-Methylanilid, Piperidid, 2-Methyl-, 3-Methyl-, 4-Metbyl-piperidid, 2,6-Dimethyl-, 3,5-Dimethylpiperidid, Morpholid und 2,6-Dimethylmorpholid in Frage.Butyl, hexyl, dihexyl, 2-ethylhexyl, octyl, ethyl octyl, decyl, Dodecyl, ethanol, diisopropanol, 3-methoxypropyl, 3- (2-ethylhexoxy) propyl, Benzylamide, anilide, N-methylanilide, piperidide, 2-methyl-, 3-methyl-, 4-methyl-piperidide, 2,6-dimethyl-, 3,5-dimethylpiperidide, morpholide and 2,6-dimethylmorpholide are possible.
Als erfindungsgemäß einzusetzende Derivate a-verzweigter Alkansäuren sind zum Beispiel Isobutyramid, 2-Ethylbuttersäurehexylester, -decylester, -diethylamid, -dibutylamid, -dihexylamid, 2-Ethylcapronsäurebutylamid, -octylamid, -2-ethylhexylamid, -S-(2-ethylhexoxy)-propylamid, -3-methoxy-propylamid, -5-methyl-2-heptylamid, -diethylamid, -dipropylamid, -di-2=butylamid, -diisobutylamid, -morpholid, -piperidid, 2,2-Dimethylcaprylsäure-allylester, -2-ethylhexylamid, -3-(2-ethylhexoxy)-propylamid, -diethylamid, -dipropylamid, 2,2-Diethylmalonsäure-diethylamid, -dibutylamid zu nennen.As derivatives of α-branched alkanoic acids to be used according to the invention are for example isobutyramide, 2-ethylbutyric acid hexyl ester, -decylester, -diethylamide, -dibutylamide, -dihexylamide, 2-ethylcaproic acid butylamide, -octylamide, -2-ethylhexylamide, -S- (2-ethylhexoxy) -propylamide, -3-methoxy-propylamide, -5-methyl-2-heptylamide, -diethylamide, -dipropylamide, -di-2 = butylamide, -diisobutylamide, -morpholide, -piperidide, 2,2-dimethylcaprylic acid allyl ester, -2-ethylhexylamide, -3- (2-ethylhexoxy) -propylamide, -diethylamide, -dipropylamide, 2,2-diethylmalonic acid-diethylamide, -dibutylamide.
Zur Herstellung der erfindungsgemäßen desodorierenden kosmetischen Zusammensetzungen können die Derivate a-verzweigter Alkansäuren in alle üblicherweise für Deodorantien gebräuchlichen Zubereitungen eingearbeitet werden wie Puder, Stifte, Roll-on und Sprays, wobei der Deo-Spray das bevorzugte Einsatzgebiet ist. Die Einarbeitung erfolgt in bekannter Weise durch einfaches Vermischen oder Lösen in den anderen Komponenten der Zubereitung wie Lösungsmitteln, Wachsen, Fettsubstanzen, Polyglykolen, Pudergrundstoffen. Die erfindungsgemäßen desodorierenden kosmetischen Zusammensetzungen enthalten dabei die Derivate a-verzweigter Alkansäuren in Mengen von O,i bis 5 Gewichtsprozent, vorzugsweise 0,5 bis 2 Gewichtsprozent, bezogen auf die gesamte Zusammensetzung.For the production of the deodorant cosmetic according to the invention Compositions can use the derivatives of α-branched alkanoic acids in any of the conventional ways preparations commonly used for deodorants such as powder, pens, Roll-on and sprays, the deodorant spray being the preferred area of application. The training takes place in a known manner by simply mixing or dissolving in the other Components of the preparation such as solvents, waxes, fatty substances, polyglycols, Powder raw materials. The deodorant cosmetic compositions according to the invention contain the derivatives of a-branched alkanoic acids in quantities from 0.1 to 5 percent by weight, preferably 0.5 to 2 percent by weight, based on the entire composition.
Die erfindungsgemäßen desodorierenden kosmetischen Zusammensetzungen werden die Derivate a-verzweigter Alkansäuren bevorzugt als alleinige Deo-Wirkstoffe enthalten, jedoch ist auch eine Kombination mit anderen desodorierenden Wirkstoffen möglich.The deodorant cosmetic compositions according to the invention the derivatives of α-branched alkanoic acids are preferred as the sole deodorant active ingredients included, but is also a combination with other deodorant active ingredients possible.
Die desodorierende Wirkung der erfindungsgemäßen kosmetischen Zusammensetzungen läßt sich steigern, wenn diese neben den Derivaten a-verzweigter Alkansäuren Antioxidantien in Mengen von 0,01 bis 1 Gewichtsprozent, vorzugsweise 0,05 bis 0,5 Gewichtsprozent, bezogen auf die gesamte Zusammensetzung enthalten.The deodorant effect of the cosmetic compositions according to the invention can be increased if these antioxidants in addition to the derivatives of α-branched alkanoic acids in amounts of 0.01 to 1 percent by weight, preferably 0.05 to 0.5 percent by weight, based on the total composition.
Als in den erfindungsgemäßen Zusammensetzungen einzusetzende Antioxidantien sind alle auf dem pharmazeutischen, kosmetischen und Nahrungsmittel-Sektor gebräuchlichen Antioxidantien geeignet und es sind folgende Produkte zu nennen: Butylhydroxytoluol, Guajakharz, Lecithin, Butylhydroxyanisol, Nordihydroguajaretsäure, Propylgallat, Octylgallat, Dodecylgallat, Tocopherole, Trihydroxybutyrophenon, Ascorbinsäure, Ascorbylpalmitat, Dilaurylthiodipropionat, Distearylthiodipropionat, Monoisopropylcitrat, Thiodipropionsäure und Citraconsäure.As antioxidants to be used in the compositions according to the invention are all used in the pharmaceutical, cosmetic and food sectors Antioxidants suitable and the following products should be mentioned: butylated hydroxytoluene, Guaiac resin, lecithin, butylhydroxyanisole, nordihydroguajaretic acid, propyl gallate, Octyl gallate, dodecyl gallate, tocopherols, trihydroxybutyrophenone, ascorbic acid, Ascorbyl palmitate, dilauryl thiodipropionate, distearyl thiodipropionate, monoisopropyl citrate, Thiodipropionic acid and citraconic acid.
Die nachfolgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn jedoch hierauf zu beschränken.The following examples are intended to illustrate the subject matter of the invention in greater detail explain without, however, restricting it to this.
Beispiele Zunächst werden einige der in den erfindungsgemäßen desodorierenden kosmetischen Zusammensetzungen einzusetzenden Derivate a-verzweigter Alkansäuren näher beschrieben. Examples First, some of the deodorants used in the present invention derivatives of α-branched alkanoic acids to be used in cosmetic compositions described in more detail.
Produkt A: 2,2-Dimethylcaprylsäure-dipropylamid.Product A: 2,2-dimethylcaprylic acid dipropylamide.
Zu einer Lösung von 15,2 g (0,15 Mol) Dipropylamin in 500 ml Ether wurden unter Kühlen und Rühren 10 g (0,05 Mol) 2,2-Dimethylcaprylsäurechlorid getropft.To a solution of 15.2 g (0.15 mol) of dipropylamine in 500 ml of ether 10 g (0.05 mol) of 2,2-dimethylcaprylic acid chloride were added dropwise with cooling and stirring.
Anschlißend wurde das Reaktionsgemisch noch 1 Stunde zum Sieden erhitzt, der Niederschlag abfiltriert, die Lösung mit verdünnter Salzsäure und mit Wasser gewaschen und über Natriumsulfat getrocknet. Der Eindampfrückstand nach dem Einengen wurde fraktioniert destilliert.The reaction mixture was then heated to boiling for a further hour, the precipitate is filtered off, the solution with dilute hydrochloric acid and with water washed and dried over sodium sulfate. The evaporation residue after concentration was fractionally distilled.
Es wurden 9,2 g an 2,2-Dimethylcaprylsäure-dipropylamid vom Siedepunkt 850 C/0,07 mbar und einem Brechungsindex n20: 1,4579 erhalten.There were 9.2 g of 2,2-dimethylcaprylic dipropylamide of boiling point 850 C / 0.07 mbar and a refractive index n20: 1.4579.
In analoger Weise wurden die nachstehenden Amide hergestellt.The following amides were prepared in an analogous manner.
Produkt B: 2,2-Dimethylcaprylsäure-diethylamid, Sdp. 1300 C/17 mbar, n20: 1,4572.Product B: 2,2-dimethylcaprylic acid diethylamide, boiling point 1300 C / 17 mbar, n20: 1.4572.
Produkt C: 2,2-Dimethylcaprylsäure-2-ethylhexylamid Sdp. 123°C/0,2 mbar, nD20: 1,4643.Product C: 2,2-dimethylcaprylic acid-2-ethylhexylamide, bp 123 ° C / 0.2 mbar, nD20: 1.4643.
Produkt D: 2,2-Dimethylcaprylsäure-3-(2-ethylhexoxy)-propylamid, Sdp. 1530 C/0,22 mbar, 20: 1 4610.Product D: 2,2-Dimethylcaprylic acid-3- (2-ethylhexoxy) -propylamide, bp. 1530 C / 0.22 mbar, 20: 1 4610.
Produkt E: Isobutyramid, Schmelzpunkt 128 - 1300 G.Product E: isobutyramide, melting point 128-1300 G.
Produkt F: 2-Ethylbuttersäure-diethylamid, Sdp. 38-40°C/0,01 mbar, nD20: 1,4424.Product F: 2-ethylbutyric acid diethylamide, boiling point 38-40 ° C / 0.01 mbar, nD20: 1.4424.
Produkt G: 2-Ethylbuttersäure-dibuthylamid, Sdp. 68-70°C C/ 0,07 mbar, nD20: 1,4478.Product G: 2-ethylbutyric acid dibutylamide, bp. 68-70 ° C / 0.07 mbar, nD20: 1.4478.
Produkt H: 2-Ethylbuttersäure-dihexylamid, Sdp. 1130 C/ 0,17 mbar, nD20: 1,4536.Product H: 2-ethylbutyric acid dihexylamide, boiling point 1130 C / 0.17 mbar, nD20: 1.4536.
Produkt J: 2-Ethylcapronsäure-butylamid, Sdp. 112°C C/ 0,07 mbar, nD20: 1,4480.Product J: 2-ethylcaproic acid-butylamide, boiling point 112 ° C / 0.07 mbar, nD20: 1.4480.
Produkt K: 2-Ethylcapronsäure-octylamid, Sdp. 1450 C/ 0,65 mbar, nD20: 1,4520.Product K: 2-ethylcaproic acid-octylamide, boiling point 1450 C / 0.65 mbar, nD20: 1.4520.
Produkt L: 2-Ethylcapronsäure-2-ethylhexylamid, Sdp. 145-146°C/0,8 mbar, nD20: 1,4515.Product L: 2-ethylcaproic acid-2-ethylhexylamide, bp 145-146 ° C / 0.8 mbar, nD20: 1.4515.
Produkt M: 2-Ethylcapronsäure-3-(2-ethylethoxy)-propylamid, Sdp. 150°C/0,07 mbar, nD20: 1,4540.Product M: 2-ethylcaproic acid 3- (2-ethylethoxy) propylamide, bp 150 ° C / 0.07 mbar, nD20: 1.4540.
Produkt N: 2-Ethylcapronsäure-3-methoxypropylamid, 20 Sdp. 119° C/0,2 mbar, n20: 1,4510.Product N: 2-ethylcaproic acid-3-methoxypropylamide, 20 bp 119 ° C / 0.2 mbar, n20: 1.4510.
Produkt 0: 2-Ethylcapronsäure-diethylamid, Sdp. 124-1250 C/20 mbar.Product 0: 2-ethylcaproic acid diethylamide, boiling point 124-1250 C / 20 mbar.
Produkt P: 2-Ethylcapronsäure-5-methyl-2-heptylamid, Sdp.141-143°C/0,6 mbar, nD20: 1,4535.Product P: 2-ethylcaproic acid-5-methyl-2-heptylamide, bp 141-143 ° C / 0.6 mbar, nD20: 1.4535.
Produkt Q: 2-Ethylcapronsäure-dipropylamid, Sdp. 65°C C/ 0,01 mbar, nD20: 1,4508.Product Q: 2-ethylcaproic acid dipropylamide, bp 65 ° C / 0.01 mbar, nD20: 1.4508.
Produkt R: 2-Ethylcapronsäure-diethylamid, Sdp.Product R: 2-ethylcaproic acid diethylamide, bp.
152°C/0,01 mbar, nD20: 1,4540. 152 ° C / 0.01 mbar, nD20: 1.4540.
Produkt S: 2-EthylcapronsSure-diisobutylamid, Sdp. 113°C/ 1,6 mbar, n20: 1,4520.Product S: 2-ethylcapronsic acid diisobutylamide, bp 113 ° C / 1.6 mbar, n20: 1.4520.
D Produkt T: 2-Ethylcapronsäure-morpholid, Sdp. 1120 C/ 0,8 mbar, 20: 1,4710. D product T: 2-ethylcaproic acid morpholide, boiling point 1120 C / 0.8 mbar, 20: 1.4710.
Produkt U: 2-Ethylcapronsäure-piperidid, Sdp. 106°C/ 0,8 mbar, nD20: 1,4719.Product U: 2-ethylcaproic acid piperidide, bp 106 ° C / 0.8 mbar, nD20: 1.4719.
Produkt V: 2,2-Diethylmalonsäure-diethylamid, Schmelzpunkt 147-148°C.Product V: 2,2-diethylmalonic acid diethylamide, melting point 147-148 ° C.
Produkt W: 2,2-Diethylmalonsäure-dibutylamid, Schmelzpunkt 88-89°C.Product W: 2,2-diethylmalonic acid dibutylamide, melting point 88-89 ° C.
Weiterhin wurden folgende Esterderivate eingesetzt.The following ester derivatives were also used.
Produkt X: 2-Ethylbuttersäure-hexylester, Sdp. 112-114°C C/ 20 22,5 mbar, nD : 1,4208.Product X: 2-ethylbutyric acid hexyl ester, bp 112-114 ° C / 20 22.5 mbar, nD: 1.4208.
Produkt Y: 2-Ethylbuttersäure-decylester, Sdp. 125-127°C C/ 0,8 mbar, nD20: 1,4322.Product Y: 2-ethylbutyric acid decyl ester, boiling point 125-127 ° C / 0.8 mbar, nD20: 1.4322.
Produkt Z: 2,2-Dimethylcaprylsäure-allylester, Sdp. 600 C/ 1,3 mbar, nD20: 1,4361.Product Z: allyl 2,2-dimethylcaprylate, boiling point 600 C / 1.3 mbar, nD20: 1.4361.
Nachstehend werden einige Beispiele für erfindungsgemäße desodorierende kosmetische Zusammensetzungen angegeben. Below are some examples of deodorants according to the invention cosmetic compositions indicated.
Desodorierender Stift 2-Octandodecanol 27,0 Gewichtsteile Cetylstearylalkohol 4,0 " Natriumstearat 9>0 Kokosfettsäuremonoethanolamid 3,0 Paraffinöl 4,0 Propylenglykol 2,0 Ethanol 49,0 Produkt A 2,0 Desodorierender Puder Reisstärke 27,0 Gewichtsteile Magnesiumcarbonat 3,0 Zinkoxid 2,0 Talkum extra fein 81,0 n Produkt G 2,0 Desodorierender Spray Produkt L 1,5 Gewichtsteile Ethanol 11>0 Isopropanol 20,5 Isopropylmyristat 2,0 Treibgas Frigen 12/114 60:40 65,0 Desodorierender Spray Produkt Q 1,3 Gewichtsteile Butylhydroxytoluol 0,2 Propylenglykol 2,5 Isopropylmyristat 2,0 Ethanol 14,0 Treibgas Frigen 11/12 50:50 80,0 Deodorant-Creme Gemisch von Mono- und Diglyceriden der Palmitin- und Stearinsäure, Cutina MD(R) Dehydag 20>5 Gewichtsteile Cetyl/Stearylalkohol+ca. 12 Mol Ethylenoxid Eumulgin B1(R) Dehydag 2,0 " Produkt T 1,3 Butylhydroxytoluol 0,2 Wasser 61,9 p-Hydroxybenzoesäuremethylester 0,1 Parfümöl 1,0 Deodorans für Pumpzerstäuber Ethanol 85,0 Gewichtesteile Isopropanol 7,2 Produkt X 1>5 Butylhydroxytoluol 0,3 Parfüm 1,0 Wasser 5,0 An die Stelle der genannten Produkte können mit gleichem Erfolg die vorstehend aufgeführten Verbindungen treten.Deodorizing stick 2-octanedodecanol 27.0 parts by weight of cetostearyl alcohol 4.0 "sodium stearate 9> 0 coconut fatty acid monoethanolamide 3.0 paraffin oil 4.0 propylene glycol 2.0 Ethanol 49.0 Product A 2.0 Deodorizing powder rice starch 27.0 parts by weight Magnesium carbonate 3.0 zinc oxide 2.0 talc, extra fine 81.0 n product G 2.0 deodorant Spray product L 1.5 parts by weight ethanol 11> 0 isopropanol 20.5 isopropyl myristate 2.0 propellant gas Frigen 12/114 60:40 65.0 deodorant spray product Q 1.3 parts by weight Butylated hydroxytoluene 0.2 Propylene glycol 2.5 Isopropyl myristate 2.0 Ethanol 14.0 Propellant Frigen 11/12 50:50 80.0 Deodorant cream Mixture of mono- and diglycerides of palmitic and stearic acid, Cutina MD (R) Dehydag 20> 5 parts by weight cetyl / stearyl alcohol + approx. 12 moles of ethylene oxide Eumulgin B1 (R) Dehydag 2.0 "product T 1.3 butylhydroxytoluene 0.2 water 61.9 methyl p-hydroxybenzoate 0.1 perfume oil 1.0 deodorant for pump atomizers Ethanol 85.0 parts by weight isopropanol 7.2 Product X 1> 5 butylhydroxytoluene 0.3 Perfume 1.0 Water 5.0 Instead of the products mentioned you can use the same Success the connections listed above will occur.
Für eine vergleichende Wirksammkeitsprüfung wurde der folgende desodorierende Spray hergestellt.For a comparative test of effectiveness, the following was deodorizing Spray made.
Desodorierender Spray A Produkt A 1,5 Gewichtsteile Isopropanol 5,5 " Ethanol 33,0 " Treibgas Frigen 12/114 60:40 60,0 Vergleichsspray B Oypryl-/Oaprinsäuretriglycerid 1,5 Gewichtsteile Isopropanol 5,5 Ethanol 33,0 ' Treibgas Frigen 121414 60:40 60,0 " Eine Testgruppe, bestehend aus 15 weiblichen und 15 männlichen Teilnehmern, benutzte zunächst 5 Tage lang eine von antimikrobiellen Mitteln freie Seife F und keine Deodorantien oder Antiperspirantien. Nach dieser Zeit erhielt jeder Teilnehmer ein T-Shirt und die Instruktion, am 6. Tage morgens nach der Wäsche mit der Seife F eine Achsel mit dem Deo-Spray A zu behandeln und die andere Achsel zum Vergleich nicht zu behandeln, wobei die eine Hälfte der Gruppe die linke Achsel, die andere Hälfte die rechte Achsel behandelte. Die Geruchsentwicklung wurde von den Versuchspersonen selbst sowie von zwei erfahrenen Kosmetikern durch Abriechen der T-Shirts nach 8 Stunden und 24 Stunden beurteilt.Deodorant spray A Product A 1.5 parts by weight isopropanol 5.5 "Ethanol 33.0" propellant gas Frigen 12/114 60:40 60.0 Comparison spray B Oypryl / Oapric acid triglyceride 1.5 parts by weight isopropanol 5.5 ethanol 33.0 'Propellant Frigen 121414 60:40 60.0 "A test group consisting of 15 females and 15 male panelists, initially used one of antimicrobial for 5 days Means free soap F and no deodorants or antiperspirants. After this At that time, each participant received a T-shirt and the instruction to do it in the morning on the 6th day After washing with the soap F, treat one armpit with the deodorant spray A and not treating the other armpit for comparison, with one half of the group the left armpit, the other half the right armpit. The odor development was carried out by the test subjects themselves and by two experienced cosmeticians T-shirts were judged after 8 hours and 24 hours.
Hiernach wurde von den Versuchspersonen eine Woche lang lediglich die Seife F benutzt.Anschließend wurde der Test wiederholt, wobei die zuvor unbehandelte Achsel mit dem Deo-Spray A behandelt wurde und die andere Achsel zum Vergleich diente.Afterwards, the test subjects only used the soap F used. The test was then repeated, with the previously untreated Armpit was treated with deodorant spray A and the other armpit was used for comparison.
In beiden Tests wurde von allen am Versuch beteiligten Personen eine sehr gute Geruchsunterbindung durch den desodorierenden Spray A festgestellt. In both tests, everyone involved in the experiment received a very good odor suppression by the deodorizing spray A found.
Mit der gleichen Testgruppe wurde der Test in völlig analoger Form wiederholt, nur daß an Stelle des Deo-Sprays A jeweils der Vergleichsspray B eingesetzt wurde. With the same test group, the test was carried out in a completely analogous manner repeated, except that the comparison spray B was used in place of the deodorant spray A became.
Bei diesem Versuch konnte von keiner der am Versuch beteiligten Personen eine signifikante Geruchsminderung festgestellt werden. In this experiment, none of the people involved in the experiment could a significant reduction in odor can be determined.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803009543 DE3009543A1 (en) | 1980-03-13 | 1980-03-13 | Deodorant cosmetic compsn. e.g. sprays and sticks - contg. alpha-branched alkanoic acid derivs. and opt. antioxidant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803009543 DE3009543A1 (en) | 1980-03-13 | 1980-03-13 | Deodorant cosmetic compsn. e.g. sprays and sticks - contg. alpha-branched alkanoic acid derivs. and opt. antioxidant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3009543A1 true DE3009543A1 (en) | 1981-09-24 |
Family
ID=6097016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803009543 Withdrawn DE3009543A1 (en) | 1980-03-13 | 1980-03-13 | Deodorant cosmetic compsn. e.g. sprays and sticks - contg. alpha-branched alkanoic acid derivs. and opt. antioxidant |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3009543A1 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3318789A1 (en) * | 1983-05-24 | 1984-11-29 | Eduard Gerlach GmbH Chemische Fabrik, 4990 Lübbecke | DEODORANT |
| DE3609425A1 (en) * | 1985-03-27 | 1986-10-02 | Colgate-Palmolive Co., New York, N.Y. | N-HIGHER ALKYL- AND ALK (EN) YLNEOALKANAMIDES METHOD FOR THE PRODUCTION THEREOF, ANTISTATIC MIXTURES WITH A CONTENT OF SUCH AMIDES AND METHODS FOR REDUCING THE STATIC CHARGING OF TEXTILES |
| US5434190A (en) * | 1986-08-08 | 1995-07-18 | Colgate-Palmolive Co. | N-aryl and N-cycloalkyl neoalkanamide insect repellents |
| WO1998056754A1 (en) * | 1997-06-11 | 1998-12-17 | L'oreal | Cosmetic composition comprising an amide and novel amides |
| WO2003097001A1 (en) * | 2002-05-16 | 2003-11-27 | The C.P. Hall Company | Methods and compositions employing a dialkyl amide |
| WO2008116338A3 (en) * | 2007-03-28 | 2008-11-13 | Givaudan Sa | Organic compounds and compositions having the ability to modulate fragrance compositions |
-
1980
- 1980-03-13 DE DE19803009543 patent/DE3009543A1/en not_active Withdrawn
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3318789A1 (en) * | 1983-05-24 | 1984-11-29 | Eduard Gerlach GmbH Chemische Fabrik, 4990 Lübbecke | DEODORANT |
| EP0126483A3 (en) * | 1983-05-24 | 1986-01-15 | Eduard Gerlach Gmbh Chemische Fabrik | Deodorant |
| DE3609425A1 (en) * | 1985-03-27 | 1986-10-02 | Colgate-Palmolive Co., New York, N.Y. | N-HIGHER ALKYL- AND ALK (EN) YLNEOALKANAMIDES METHOD FOR THE PRODUCTION THEREOF, ANTISTATIC MIXTURES WITH A CONTENT OF SUCH AMIDES AND METHODS FOR REDUCING THE STATIC CHARGING OF TEXTILES |
| FR2579590A1 (en) * | 1985-03-27 | 1986-10-03 | Colgate Palmolive Co | N- (ALKYL OR HIGHER ALKENYL) ANTISTATIC NEOALCANOAMIDES, PROCESS FOR THEIR PRODUCTION, DETERGENT CONTAINING COMPOSITION AND METHODS FOR WASHING AND / OR TREATING LAUNDRY USING THE SAME |
| GB2173792A (en) * | 1985-03-27 | 1986-10-22 | Colgate Palmolive Co | N-higher alk(en)yl neoalkanoamides and their use as antistatic compounds |
| GB2173792B (en) * | 1985-03-27 | 1989-12-28 | Colgate Palmolive Co | Antistatic compositions containing n-higher alk(en)yl neoalkanoamides |
| AT395420B (en) * | 1985-03-27 | 1992-12-28 | Colgate Palmolive Co | METHOD FOR THE PRODUCTION OF ALK (EN) -YLNEOALKANAMIDES, ANTISTATIC MIXTURES WITH A CONTENT OF SUCH AMIDES AND METHOD FOR REDUCING THE STATIC CHARGE OF TEXTILES |
| US5434190A (en) * | 1986-08-08 | 1995-07-18 | Colgate-Palmolive Co. | N-aryl and N-cycloalkyl neoalkanamide insect repellents |
| WO1998056754A1 (en) * | 1997-06-11 | 1998-12-17 | L'oreal | Cosmetic composition comprising an amide and novel amides |
| FR2764602A1 (en) * | 1997-06-11 | 1998-12-18 | Oreal | COSMETIC COMPOSITION COMPRISING AN AMIDE AND NEW AMIDES |
| US6359175B1 (en) | 1997-06-11 | 2002-03-19 | L'oreal S.A. | Cosmetic composition comprising an amide and novel amides |
| US6515178B2 (en) | 1997-06-11 | 2003-02-04 | L'oreal | Cosmetic composition comprising an amide, and novel amides |
| WO2003097001A1 (en) * | 2002-05-16 | 2003-11-27 | The C.P. Hall Company | Methods and compositions employing a dialkyl amide |
| WO2008116338A3 (en) * | 2007-03-28 | 2008-11-13 | Givaudan Sa | Organic compounds and compositions having the ability to modulate fragrance compositions |
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