CA2250837C - Betaine ester compounds of active alcohols - Google Patents
Betaine ester compounds of active alcohols Download PDFInfo
- Publication number
- CA2250837C CA2250837C CA002250837A CA2250837A CA2250837C CA 2250837 C CA2250837 C CA 2250837C CA 002250837 A CA002250837 A CA 002250837A CA 2250837 A CA2250837 A CA 2250837A CA 2250837 C CA2250837 C CA 2250837C
- Authority
- CA
- Canada
- Prior art keywords
- hydrochloride
- ester
- oxoethyl
- composition according
- glycine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 Betaine ester compounds Chemical class 0.000 title claims abstract description 127
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 229960003237 betaine Drugs 0.000 title claims abstract description 39
- 150000001298 alcohols Chemical class 0.000 title abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 111
- 239000004094 surface-active agent Substances 0.000 claims abstract description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 45
- 230000002378 acidificating effect Effects 0.000 claims abstract description 45
- 239000000693 micelle Substances 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 50
- 150000002148 esters Chemical class 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000002304 perfume Substances 0.000 claims description 32
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 26
- 239000004471 Glycine Substances 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
- 239000003093 cationic surfactant Substances 0.000 claims description 16
- MVYRCGLBWXZUFP-UHFFFAOYSA-N 2-(didodecylamino)acetic acid Chemical group CCCCCCCCCCCCN(CC(O)=O)CCCCCCCCCCCC MVYRCGLBWXZUFP-UHFFFAOYSA-N 0.000 claims description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 14
- 239000006185 dispersion Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- HVSYQIIFVJACKZ-UHFFFAOYSA-N 2-(dioctylamino)acetic acid Chemical compound CCCCCCCCN(CC(O)=O)CCCCCCCC HVSYQIIFVJACKZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 11
- 239000004744 fabric Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000005792 Geraniol Substances 0.000 claims description 10
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 10
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 10
- 229940113087 geraniol Drugs 0.000 claims description 10
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 10
- LNPHVNNRZGCOBK-UHFFFAOYSA-N 2-(dodecylazaniumyl)acetate Chemical group CCCCCCCCCCCCNCC(O)=O LNPHVNNRZGCOBK-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 239000002979 fabric softener Substances 0.000 claims description 7
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 6
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 6
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 5
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 5
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 5
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 5
- 239000003945 anionic surfactant Substances 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 5
- 125000002091 cationic group Chemical group 0.000 claims description 5
- 235000000484 citronellol Nutrition 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 229930007744 linalool Natural products 0.000 claims description 5
- 239000002736 nonionic surfactant Substances 0.000 claims description 5
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 claims description 4
- OXYRENDGHPGWKV-UHFFFAOYSA-N 3-methyl-5-phenylpentan-1-ol Chemical compound OCCC(C)CCC1=CC=CC=C1 OXYRENDGHPGWKV-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- JMJCHFPFLZGPQJ-UHFFFAOYSA-N 2-[[2-(3,7-dimethylocta-1,6-dien-3-yloxy)-2-oxoethyl]-dodecylamino]acetic acid Chemical compound C(CCCCCCCCCCC)N(CC(=O)O)CC(=O)OC(C)(C=C)CCC=C(C)C JMJCHFPFLZGPQJ-UHFFFAOYSA-N 0.000 claims description 3
- BEGOTEZHAOWXBI-UHFFFAOYSA-N 2-[bis[2-(3,7-dimethylocta-1,6-dien-3-yloxy)-2-oxoethyl]amino]acetic acid Chemical compound C(C)(C=C)(CCC=C(C)C)OC(CN(CC(=O)O)CC(OC(C)(C=C)CCC=C(C)C)=O)=O BEGOTEZHAOWXBI-UHFFFAOYSA-N 0.000 claims description 3
- ILQVWXBPLGKVAP-UHFFFAOYSA-N 2-[butyl-[2-(3,7-dimethylocta-1,6-dien-3-yloxy)-2-oxoethyl]amino]acetic acid Chemical compound C(CCC)N(CC(=O)O)CC(=O)OC(C)(C=C)CCC=C(C)C ILQVWXBPLGKVAP-UHFFFAOYSA-N 0.000 claims description 3
- SMNDMNGBMYISEO-MHWRWJLKSA-N 2-[butyl-[2-[(2E)-3,7-dimethylocta-2,6-dienoxy]-2-oxoethyl]amino]acetic acid Chemical group C(CCC)N(CC(=O)O)CC(=O)OC\C=C(/C)\CCC=C(C)C SMNDMNGBMYISEO-MHWRWJLKSA-N 0.000 claims description 3
- NMJSXCIYPCETPL-HKOYGPOVSA-N C(CCCCCCCCCCC)N(CC(=O)O)CC(=O)OC\C=C(/C)\CCC=C(C)C Chemical group C(CCCCCCCCCCC)N(CC(=O)O)CC(=O)OC\C=C(/C)\CCC=C(C)C NMJSXCIYPCETPL-HKOYGPOVSA-N 0.000 claims description 3
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 3
- 239000005770 Eugenol Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 229930008394 dihydromyrcenol Natural products 0.000 claims description 3
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 claims description 3
- 229960002217 eugenol Drugs 0.000 claims description 3
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229940067107 phenylethyl alcohol Drugs 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 2
- XGRCZWYTJSFHET-UHFFFAOYSA-N (2,4-dimethylcyclohex-3-en-1-yl)methanol Chemical compound CC1C=C(C)CCC1CO XGRCZWYTJSFHET-UHFFFAOYSA-N 0.000 claims description 2
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 claims description 2
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 claims description 2
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 2
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 claims description 2
- VKOKTTXFGFTZMM-MSKUYSOUSA-N C(\C=C(/C)\CCC=C(C)C)OC(CN(CC(=O)O)CC(OC\C=C(/C)\CCC=C(C)C)=O)=O Chemical group C(\C=C(/C)\CCC=C(C)C)OC(CN(CC(=O)O)CC(OC\C=C(/C)\CCC=C(C)C)=O)=O VKOKTTXFGFTZMM-MSKUYSOUSA-N 0.000 claims description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 2
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 claims description 2
- KDBOLXNSBAMLOW-UHFFFAOYSA-M bis[2-(3,7-dimethylocta-1,6-dien-3-yloxy)-2-oxoethyl]-dimethylazanium;bromide Chemical compound [Br-].CC(C)=CCCC(C)(C=C)OC(=O)C[N+](C)(C)CC(=O)OC(C)(C=C)CCC=C(C)C KDBOLXNSBAMLOW-UHFFFAOYSA-M 0.000 claims description 2
- 239000004665 cationic fabric softener Substances 0.000 claims description 2
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 229930002886 farnesol Natural products 0.000 claims description 2
- 229940043259 farnesol Drugs 0.000 claims description 2
- 229940041616 menthol Drugs 0.000 claims description 2
- 229960005323 phenoxyethanol Drugs 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
- 229940116411 terpineol Drugs 0.000 claims description 2
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 claims description 2
- QIFXMRGHNROGMB-XGPVMEEKSA-M bis[2-[(2e)-3,7-dimethylocta-2,6-dienoxy]-2-oxoethyl]-dimethylazanium;bromide Chemical group [Br-].CC(C)=CCC\C(C)=C\COC(=O)C[N+](C)(C)CC(=O)OC\C=C(/C)CCC=C(C)C QIFXMRGHNROGMB-XGPVMEEKSA-M 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
- 235000019441 ethanol Nutrition 0.000 description 50
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 239000000344 soap Substances 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 12
- 239000003760 tallow Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000003860 storage Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 8
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 8
- 229940089960 chloroacetate Drugs 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 7
- 238000007046 ethoxylation reaction Methods 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 150000002191 fatty alcohols Chemical class 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical class C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 235000019634 flavors Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 150000001720 carbohydrates Chemical group 0.000 description 4
- WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 3
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000008051 alkyl sulfates Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- IRAQOCYXUMOFCW-OSFYFWSMSA-N cedr-8-ene Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C(C)=CC2 IRAQOCYXUMOFCW-OSFYFWSMSA-N 0.000 description 3
- WTEVQBCEXWBHNA-JXMROGBWSA-N citral A Natural products CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000003935 denaturing gradient gel electrophoresis Methods 0.000 description 3
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 3
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- KUSOHEBAOQJUOL-UHFFFAOYSA-N methyl 2-(dioctylamino)acetate Chemical compound CCCCCCCCN(CC(=O)OC)CCCCCCCC KUSOHEBAOQJUOL-UHFFFAOYSA-N 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- DYLPEFGBWGEFBB-OSFYFWSMSA-N (+)-β-cedrene Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C(=C)CC2 DYLPEFGBWGEFBB-OSFYFWSMSA-N 0.000 description 2
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 2
- IYAQFFOKAFGDKE-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-3-ium;methyl sulfate Chemical compound C1CN=CN1.COS(O)(=O)=O IYAQFFOKAFGDKE-UHFFFAOYSA-N 0.000 description 2
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- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
- C11D3/0015—Softening compositions liquid
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/65—Mixtures of anionic with cationic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
- C11D3/502—Protected perfumes
- C11D3/507—Compounds releasing perfumes by thermal or chemical activation
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96302291A EP0799885A1 (en) | 1996-04-01 | 1996-04-01 | Betaine ester compounds of active alcohols |
| EP96302291.8 | 1996-04-01 | ||
| PCT/US1997/004959 WO1997036978A1 (en) | 1996-04-01 | 1997-03-27 | Betaine ester compounds of active alcohols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2250837A1 CA2250837A1 (en) | 1997-10-09 |
| CA2250837C true CA2250837C (en) | 2002-02-19 |
Family
ID=8224873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002250837A Expired - Fee Related CA2250837C (en) | 1996-04-01 | 1997-03-27 | Betaine ester compounds of active alcohols |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0799885A1 (pt) |
| JP (1) | JP3770916B2 (pt) |
| CN (1) | CN1220693A (pt) |
| AR (1) | AR008583A1 (pt) |
| AU (1) | AU2590897A (pt) |
| BR (1) | BR9710416A (pt) |
| CA (1) | CA2250837C (pt) |
| WO (1) | WO1997036978A1 (pt) |
| ZA (1) | ZA972775B (pt) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19948667A1 (de) * | 1999-10-08 | 2001-04-12 | Henkel Kgaa | Reinigungsmittelkomponente mit doppelkontrollierter Duftfreisetzung |
| ATE309199T1 (de) | 1999-10-18 | 2005-11-15 | Firmenich & Cie | Ester mit einer sekundären carbamoylgruppe und deren verwendung als ausgangsstoffe von duftenden alkoholen |
| WO2002077074A1 (en) | 2001-03-27 | 2002-10-03 | Firmenich Sa | Compounds for a controlled release of active compounds |
| DE10132174A1 (de) * | 2001-07-03 | 2003-03-27 | Goldschmidt Ag Th | Neue Betainester |
| DE10132173A1 (de) | 2001-07-03 | 2003-01-23 | Goldschmidt Ag Th | Neue Betainester |
| DE10153183A1 (de) * | 2001-10-27 | 2003-05-15 | Henkel Kgaa | Betainesterhaltige Mittel |
| DE10217705A1 (de) * | 2002-04-20 | 2003-11-06 | Goldschmidt Ag Th | Wäscheweichspülformulierungen enthaltend Betainesterderivate sowie Verfahren zur Verbesserung der Waschleistung von Waschmitteln |
| AU2003255460A1 (en) * | 2002-08-27 | 2004-03-19 | Ciba Specialty Chemicals Holding Inc. | Method for delivering biologically active substances |
| MX2007015358A (es) | 2005-06-09 | 2008-02-15 | Evonik Degussa Gmbh | Polixiloxano liberador de fragancia alcoholica. |
| EP2074154B1 (en) | 2006-10-10 | 2011-03-09 | Firmenich SA | Polymer conjugates for a controlled release of active molecules |
| US20080139378A1 (en) * | 2006-12-07 | 2008-06-12 | Degussa Ag | Urine-absorbing composition with fragrance release upon use |
| DE102007012910A1 (de) | 2007-03-19 | 2008-09-25 | Momentive Performance Materials Gmbh | Mit Duftstoffen modifizierte, verzweigte Polyorganosiloxane |
| DE102007012909A1 (de) | 2007-03-19 | 2008-09-25 | Momentive Performance Materials Gmbh | Mit Duftstoffen modifizierte, reaktive Polyorganosiloxane |
| BRPI0811961A2 (pt) | 2007-05-22 | 2014-11-11 | Firmenich & Cie | Derivados 1,3-diaza-4-oxo-heterocíclicos de 3 a 7 membros capazes de liberar aldeídos ou cetonas ativos |
| WO2008155683A1 (en) | 2007-06-18 | 2008-12-24 | Firmenich Sa | Malodor counteracting compositions and method for their use |
| DE102007037147A1 (de) | 2007-08-07 | 2009-02-12 | Henkel Ag & Co. Kgaa | Duftkomposite mit verbesserter Duftfreisetzung |
| EP2828240B1 (en) | 2012-03-20 | 2018-10-31 | Firmenich SA | Compounds for a controlled release of active perfuming molecules |
| US20150284660A1 (en) | 2012-08-21 | 2015-10-08 | Firmenich Sa | Method to improve the performance of encapsulated fragrances |
| CN104661740B (zh) | 2012-09-24 | 2017-04-12 | 弗门尼舍有限公司 | 多层化核/壳微胶囊 |
| US9585826B2 (en) * | 2012-11-07 | 2017-03-07 | Kimberly-Clark Worldwide, Inc. | Triggerable compositions for two-stage, controlled release of active chemistry |
| BR112015027665B1 (pt) | 2013-06-19 | 2022-05-31 | Firmenich Sa | Conjugados de polissiloxano como sistemas de liberação de fragrância |
| US9758749B2 (en) | 2013-09-09 | 2017-09-12 | Firmenich Sa | Thioether derivatives as precursors for a controlled release of active molecules |
| US9902920B2 (en) | 2014-12-10 | 2018-02-27 | Firmenich Sa | Polysiloxanes as fragrance delivery systems in fine perfumery |
| JP6713474B2 (ja) | 2015-01-21 | 2020-06-24 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | 活性揮発性カルボニル化合物の制御放出のための光解離性アセタールおよびケタール化合物 |
| CN107250339B (zh) | 2015-02-17 | 2020-07-17 | 弗门尼舍有限公司 | 用于加香成分受控释放的由聚(天冬氨酸)衍生的共聚物 |
| MX2018014674A (es) | 2016-06-30 | 2019-02-28 | Firmenich & Cie | Microcapsulas de nucleo y capa de revestimiento compuesto. |
| CN108342263B (zh) * | 2017-01-25 | 2022-01-28 | 花王株式会社 | 液体清洁剂组合物 |
| CN108387559B (zh) * | 2018-01-15 | 2023-05-12 | 南方医科大学 | 一种表面活性剂临界胶束浓度试纸及其制备方法 |
| WO2019243369A1 (en) | 2018-06-21 | 2019-12-26 | Firmenich Sa | Compounds for providing a long-lasting strawberry odor |
| MX2021002512A (es) | 2018-12-20 | 2021-04-28 | Firmenich & Cie | Properfume de alquil-enol-eter. |
| WO2021023670A1 (en) | 2019-08-08 | 2021-02-11 | Firmenich Sa | Compounds for providing a long-lasting mint odor |
| JP2023504345A (ja) | 2019-12-03 | 2023-02-03 | フイルメニツヒ ソシエテ アノニム | エノールエーテル香料前駆体 |
| MX2022002595A (es) | 2019-12-19 | 2022-03-25 | Firmenich & Cie | Compuestos para proporcionar un olor floral y frutal de larga duracion. |
| WO2021123144A1 (en) | 2019-12-20 | 2021-06-24 | Firmenich Sa | Pro-perfume compositions |
| IL295686A (en) | 2020-04-14 | 2022-10-01 | Firmenich & Cie | Compounds for providing long-lasting odor |
| WO2021250164A1 (en) | 2020-06-12 | 2021-12-16 | Firmenich Sa | Enol ether properfume |
| WO2022084437A1 (en) | 2020-10-21 | 2022-04-28 | Firmenich Sa | Improved freshness imparting compositions |
| WO2023067063A1 (en) | 2021-10-20 | 2023-04-27 | Firmenich Sa | Improved perfume compositions comprising sulfur-containing pro-fragrance compounds |
| JP2024537975A (ja) | 2021-10-20 | 2024-10-18 | フイルメニツヒ ソシエテ アノニム | 硫黄含有プロフレグランス化合物を含む改善された香料組成物 |
| IL311959A (en) | 2021-11-03 | 2024-06-01 | Firmenich & Cie | Acetals and Cyclic Kills for the Light-Induced Release of Active Aldehydes and Ketones |
| WO2023111006A1 (en) | 2021-12-14 | 2023-06-22 | Firmenich Sa | Enol ether properfume |
| WO2024218086A1 (en) | 2023-04-17 | 2024-10-24 | Firmenich Sa | Photolabile cyclic acetals and ketals for the light-induced delivery of active aldehydes and ketones |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1950643A1 (de) * | 1969-10-08 | 1971-04-15 | Manzke Oswald Dr Dipl Chem | Quaternaere Ammoniumverbindungen zur Herstellung von Koerperpflegemitteln |
| US4256600A (en) * | 1978-03-13 | 1981-03-17 | The Greyhound Corp. | Translucent soap bar containing citronellyl esters as lime soap dispersants |
| DE3505269A1 (de) * | 1985-02-15 | 1986-08-21 | Hoechst Ag, 6230 Frankfurt | Quarternaere alkylamidobetainester, ein verfahren zu ihrer herstellung und ihre verwendung in waescheweichspuelmitteln |
| DE3527974C2 (de) * | 1985-08-03 | 1994-08-04 | Wella Ag | Saures Haarpflegemittel |
| US4808321A (en) * | 1987-05-01 | 1989-02-28 | The Procter & Gamble Company | Mono-esters as fiber and fabric treatment compositions |
| JP4030577B2 (ja) * | 1993-09-30 | 2008-01-09 | ザ、プロクター、エンド、ギャンブル、カンパニー | 活性物質デリバリー系 |
| EP0752465A1 (en) * | 1995-06-01 | 1997-01-08 | The Procter & Gamble Company | Betaine esters for delivery of alcohols |
| US5562847A (en) * | 1995-11-03 | 1996-10-08 | The Procter & Gamble Company | Dryer-activated fabric conditioning and antistatic compositions with improved perfume longevity |
-
1996
- 1996-04-01 EP EP96302291A patent/EP0799885A1/en not_active Withdrawn
-
1997
- 1997-03-27 CN CN97195159A patent/CN1220693A/zh active Pending
- 1997-03-27 AU AU25908/97A patent/AU2590897A/en not_active Abandoned
- 1997-03-27 JP JP53540697A patent/JP3770916B2/ja not_active Expired - Fee Related
- 1997-03-27 BR BR9710416A patent/BR9710416A/pt not_active Application Discontinuation
- 1997-03-27 WO PCT/US1997/004959 patent/WO1997036978A1/en active Application Filing
- 1997-03-27 CA CA002250837A patent/CA2250837C/en not_active Expired - Fee Related
- 1997-04-01 AR ARP970101299A patent/AR008583A1/es unknown
- 1997-04-01 ZA ZA9702775A patent/ZA972775B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR008583A1 (es) | 2000-02-09 |
| CA2250837A1 (en) | 1997-10-09 |
| JP3770916B2 (ja) | 2006-04-26 |
| EP0799885A1 (en) | 1997-10-08 |
| AU2590897A (en) | 1997-10-22 |
| JP2000509107A (ja) | 2000-07-18 |
| WO1997036978A1 (en) | 1997-10-09 |
| CN1220693A (zh) | 1999-06-23 |
| BR9710416A (pt) | 1999-08-17 |
| ZA972775B (en) | 1997-10-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |