MXPA01000365A - Amine reaction compounds comprising one or more active ingredient - Google Patents
Amine reaction compounds comprising one or more active ingredientInfo
- Publication number
- MXPA01000365A MXPA01000365A MXPA/A/2001/000365A MXPA01000365A MXPA01000365A MX PA01000365 A MXPA01000365 A MX PA01000365A MX PA01000365 A MXPA01000365 A MX PA01000365A MX PA01000365 A MXPA01000365 A MX PA01000365A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- amine
- amino
- mixtures
- further characterized
- Prior art date
Links
- 239000004480 active ingredient Substances 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 title claims description 123
- 150000001412 amines Chemical class 0.000 title claims description 64
- 238000006243 chemical reaction Methods 0.000 title abstract description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 51
- 239000000203 mixture Substances 0.000 claims description 245
- -1 poly [oxy (methyl-1,2-ethanediyl)] Polymers 0.000 claims description 104
- 239000002304 perfume Substances 0.000 claims description 85
- 150000001299 aldehydes Chemical class 0.000 claims description 80
- 239000004744 fabric Substances 0.000 claims description 77
- 229920000768 polyamine Polymers 0.000 claims description 67
- 239000007795 chemical reaction product Substances 0.000 claims description 61
- 239000000463 material Substances 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 150000002576 ketones Chemical group 0.000 claims description 42
- 239000003795 chemical substances by application Substances 0.000 claims description 28
- 239000004615 ingredient Substances 0.000 claims description 25
- VAMXMNNIEUEQDV-UHFFFAOYSA-N Methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 229920002873 Polyethylenimine Polymers 0.000 claims description 20
- 239000003205 fragrance Substances 0.000 claims description 20
- 229910001868 water Inorganic materials 0.000 claims description 16
- 229920000858 Cyclodextrin Polymers 0.000 claims description 15
- 239000000412 dendrimer Substances 0.000 claims description 15
- 229920000736 dendritic polymer Polymers 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 12
- 239000000969 carrier Substances 0.000 claims description 12
- 239000001913 cellulose Substances 0.000 claims description 12
- 229920002678 cellulose Polymers 0.000 claims description 12
- 229940102398 methyl anthranilate Drugs 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 150000004676 glycans Polymers 0.000 claims description 10
- 229920001282 polysaccharide Polymers 0.000 claims description 10
- 239000005017 polysaccharide Substances 0.000 claims description 10
- 150000004804 polysaccharides Polymers 0.000 claims description 10
- KSMVZQYAVGTKIV-UHFFFAOYSA-N Decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 claims description 9
- SZXQTJUDPRGNJN-UHFFFAOYSA-N Dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 9
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- NAQMVNRVTILPCV-UHFFFAOYSA-N Hexamethylenediamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 8
- 229920002472 Starch Polymers 0.000 claims description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000008107 starch Substances 0.000 claims description 8
- NEHNMFOYXAPHSD-JTQLQIEISA-N (S)-(-)-citronellal Natural products O=CC[C@@H](C)CCC=C(C)C NEHNMFOYXAPHSD-JTQLQIEISA-N 0.000 claims description 7
- ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-UHFFFAOYSA-N 0.000 claims description 7
- BLFLLBZGZJTVJG-UHFFFAOYSA-N Benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 claims description 7
- 239000001116 FEMA 4028 Substances 0.000 claims description 7
- SATCULPHIDQDRE-UHFFFAOYSA-N Piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 claims description 7
- 235000001014 amino acid Nutrition 0.000 claims description 7
- 150000001413 amino acids Chemical class 0.000 claims description 7
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 claims description 7
- ZRSNZINYAWTAHE-UHFFFAOYSA-N 4-Anisaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 6
- 229920002307 Dextran Polymers 0.000 claims description 6
- BJHIKXHVCXFQLS-UYFOZJQFSA-N Fructose Natural products OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 claims description 6
- JARKCYVAAOWBJS-UHFFFAOYSA-N Hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 claims description 6
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 6
- PSQYTAPXSHCGMF-BQYQJAHWSA-N beta-ionone Natural products CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 6
- WGPCZPLRVAWXPW-LLVKDONJSA-N gamma-Dodecalactone Natural products CCCCCCCC[C@@H]1CCC(=O)O1 WGPCZPLRVAWXPW-LLVKDONJSA-N 0.000 claims description 6
- 150000002482 oligosaccharides Polymers 0.000 claims description 6
- 239000005720 sucrose Substances 0.000 claims description 6
- PHXATPHONSXBIL-JTQLQIEISA-N γ-undecanolactone Chemical compound CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 claims description 6
- XEJGJTYRUWUFFD-FNORWQNLSA-N (E)-1-(2,6,6-trimethyl-1-cyclohex-3-enyl)but-2-en-1-one Chemical compound C\C=C\C(=O)C1C(C)C=CCC1(C)C XEJGJTYRUWUFFD-FNORWQNLSA-N 0.000 claims description 5
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims description 5
- AKGGYBADQZYZPD-UHFFFAOYSA-N Benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 claims description 5
- CZMRCDWAGMRECN-UGDNZRGBSA-N D-sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 5
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 claims description 5
- POIARNZEYGURDG-FNORWQNLSA-N Damascenone Chemical compound C\C=C\C(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-FNORWQNLSA-N 0.000 claims description 5
- 241000238631 Hexapoda Species 0.000 claims description 5
- CZMRCDWAGMRECN-GDQSFJPYSA-N Sucrose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)[C@@]1(CO)[C@H](O)[C@@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-GDQSFJPYSA-N 0.000 claims description 5
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N cinnamic aldehyde Natural products O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims description 5
- 229930003633 citronellal Natural products 0.000 claims description 5
- 235000000983 citronellal Nutrition 0.000 claims description 5
- IPWBXORAIBJDDQ-UHFFFAOYSA-N methyl 2-hexyl-3-oxocyclopentane-1-carboxylate Chemical compound CCCCCCC1C(C(=O)OC)CCC1=O IPWBXORAIBJDDQ-UHFFFAOYSA-N 0.000 claims description 5
- 235000019698 starch Nutrition 0.000 claims description 5
- 229930007850 β-damascenone Natural products 0.000 claims description 5
- ULDHMXUKGWMISQ-VIFPVBQESA-N (+)-(4S)-carvone Chemical compound CC(=C)[C@H]1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-VIFPVBQESA-N 0.000 claims description 4
- 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 claims description 4
- MBDOYVRWFFCFHM-SNAWJCMRSA-N 2-Hexenal Chemical compound CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 claims description 4
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-Methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 claims description 4
- 239000005973 Carvone Substances 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 4
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 4
- GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 claims description 4
- 150000001448 anilines Chemical class 0.000 claims description 4
- 230000000845 anti-microbial Effects 0.000 claims description 4
- 239000004599 antimicrobial Substances 0.000 claims description 4
- 229940095076 benzaldehyde Drugs 0.000 claims description 4
- 229930007075 carvone Natural products 0.000 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229920000962 poly(amidoamine) Polymers 0.000 claims description 4
- OFHHDSQXFXLTKC-UHFFFAOYSA-N undec-10-enal Chemical group C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 claims description 4
- UZFLPKAIBPNNCA-BQYQJAHWSA-N α-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 claims description 4
- 239000001674 (E)-1-(2,6,6-trimethyl-1-cyclohexenyl)but-2-en-1-one Substances 0.000 claims description 3
- NUWFGSCHUJWGHJ-OUKQBFOZSA-N (E)-1-phenylnon-1-en-3-one Chemical compound CCCCCCC(=O)\C=C\C1=CC=CC=C1 NUWFGSCHUJWGHJ-OUKQBFOZSA-N 0.000 claims description 3
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical compound NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 claims description 3
- 229920001661 Chitosan Polymers 0.000 claims description 3
- GZCGUPFRVQAUEE-KCDKBNATSA-N D-(+)-Galactose Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-KCDKBNATSA-N 0.000 claims description 3
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 3
- BGTBFNDXYDYBEY-FNORWQNLSA-N Damascone Chemical compound C\C=C\C(=O)C1=C(C)CCCC1(C)C BGTBFNDXYDYBEY-FNORWQNLSA-N 0.000 claims description 3
- 239000005715 Fructose Substances 0.000 claims description 3
- 229940020436 Gamma-undecalactone Drugs 0.000 claims description 3
- YJSUCBQWLKRPDL-UHFFFAOYSA-N Isocyclocitral Chemical compound CC1CC(C)=CC(C)C1C=O YJSUCBQWLKRPDL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001241 acetals Chemical class 0.000 claims description 3
- 229930007098 alpha-ionone Natural products 0.000 claims description 3
- 125000005001 aminoaryl group Chemical group 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 3
- HZYHMHHBBBSGHB-UHFFFAOYSA-N nona-2,6-dienal Chemical compound CCC=CCCC=CC=O HZYHMHHBBBSGHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000005871 repellent Substances 0.000 claims description 3
- 230000002940 repellent Effects 0.000 claims description 3
- WQZGKKKJIJFFOK-PHYPRBDBSA-N α-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N β-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 3
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1S,2S)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims description 2
- STMZGJLCKJFMLQ-UHFFFAOYSA-N 2-[3-(2-aminoethyl)cyclohexyl]ethanamine Chemical compound NCCC1CCCC(CCN)C1 STMZGJLCKJFMLQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims description 2
- 229960001230 Asparagine Drugs 0.000 claims description 2
- 229960005261 Aspartic Acid Drugs 0.000 claims description 2
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N DETA Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- 229960002989 Glutamic Acid Drugs 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- 229920000057 Mannan Polymers 0.000 claims description 2
- LUEWUZLMQUOBSB-GFVSVBBRSA-N Mannan Chemical compound O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@H]3[C@H](O[C@@H](O)[C@@H](O)[C@H]3O)CO)[C@@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-GFVSVBBRSA-N 0.000 claims description 2
- 229960005190 Phenylalanine Drugs 0.000 claims description 2
- 239000004473 Threonine Substances 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- 235000009697 arginine Nutrition 0.000 claims description 2
- 235000009582 asparagine Nutrition 0.000 claims description 2
- 235000003704 aspartic acid Nutrition 0.000 claims description 2
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 claims description 2
- 229940117916 cinnamic aldehyde Drugs 0.000 claims description 2
- 229930007907 citral Natural products 0.000 claims description 2
- 229940043350 citral Drugs 0.000 claims description 2
- 239000002826 coolant Substances 0.000 claims description 2
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims description 2
- 235000013922 glutamic acid Nutrition 0.000 claims description 2
- 239000004220 glutamic acid Substances 0.000 claims description 2
- 235000004554 glutamine Nutrition 0.000 claims description 2
- 235000018977 lysine Nutrition 0.000 claims description 2
- WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 claims description 2
- BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims description 2
- HGRXBNZHQKXDPL-UHFFFAOYSA-N phenyl 4-aminobenzoate Chemical compound C1=CC(N)=CC=C1C(=O)OC1=CC=CC=C1 HGRXBNZHQKXDPL-UHFFFAOYSA-N 0.000 claims description 2
- 229920000333 poly(propyleneimine) Polymers 0.000 claims description 2
- KYWIYKKSMDLRDC-UHFFFAOYSA-N 2-Undecanone Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 claims 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-M 4-aminobenzoate Chemical class NC1=CC=C(C([O-])=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-M 0.000 claims 1
- 229920002907 Guar gum Polymers 0.000 claims 1
- 239000006001 Methyl nonyl ketone Substances 0.000 claims 1
- 150000007860 aryl ester derivatives Chemical class 0.000 claims 1
- 229920001542 oligosaccharide Chemical group 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract description 24
- 210000002356 Skeleton Anatomy 0.000 description 41
- 235000019645 odor Nutrition 0.000 description 38
- 239000000126 substance Substances 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
- 239000002253 acid Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- 125000004432 carbon atoms Chemical group C* 0.000 description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 22
- 239000003981 vehicle Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 235000014113 dietary fatty acids Nutrition 0.000 description 20
- 239000000194 fatty acid Substances 0.000 description 20
- 125000002947 alkylene group Chemical group 0.000 description 19
- 150000004665 fatty acids Chemical group 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 17
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 16
- 239000002738 chelating agent Substances 0.000 description 15
- 125000005647 linker group Chemical group 0.000 description 15
- 239000005977 Ethylene Substances 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- 239000002689 soil Substances 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000003760 tallow Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 13
- 230000002194 synthesizing Effects 0.000 description 13
- 150000001768 cations Chemical group 0.000 description 12
- 238000006467 substitution reaction Methods 0.000 description 12
- 239000006071 cream Substances 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 11
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 125000002640 tocopherol group Chemical group 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 229930003799 tocopherols Natural products 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- PANBRUWVURLWGY-UHFFFAOYSA-N undec-2-enal Chemical compound CCCCCCCCC=CC=O PANBRUWVURLWGY-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- LUZDYPLAQQGJEA-UHFFFAOYSA-N Β-Naphthol methyl ether Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 1
- IGODOXYLBBXFDW-UHFFFAOYSA-N α-Terpinyl acetate Chemical compound CC(=O)OC(C)(C)C1CCC(C)=CC1 IGODOXYLBBXFDW-UHFFFAOYSA-N 0.000 description 1
- LKDRXBCSQODPBY-DPYQTVNSSA-N β-D-tagatopyranose Chemical compound OC[C@@]1(O)OC[C@@H](O)[C@H](O)[C@@H]1O LKDRXBCSQODPBY-DPYQTVNSSA-N 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N β-cyclodextrin Chemical class OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
Abstract
The present invention relates to a product of reaction between a primary and/or secondary amine and one or more active ingredients. By the present invention, there is provided a release of the active component over a longer period of time than by the use of the active itself.
Description
AMINO TYPE REACTION COMPOUNDS COMPRISING ONE OR MORE ACTIVE INGREDIENTS
FIELD OF THE INVENTION
The present invention relates to a reaction product between an amine and an active component, in particular an active aldehyde or ketone, more preferred an aldehyde or ketone perfume. More particularly, the invention relates to such reaction products for use in softening compositions.
BACKGROUND OF THE INVENTION
The perfumed products are well known in the art. However, the acceptance by the consumer of such perfumed products as softening products is determined not only by the performance achieved with these products, but also by the aesthetic aspects associated therewith. The perfume components are, therefore, an important aspect of the successful formulation of such commercial products. Consumers also want treated fabrics to keep the fragrance pleasant over time. Indeed, the perfume additives make such compositions more aesthetically pleasing to the consumer, and in some cases the perfume imparts a pleasant fragrance to the fabrics treated therewith. However, the amount of perfume carried from an aqueous laundry solution onto the fabrics is often marginal, and does not last long on them. In addition, fragrance materials are often very expensive, and their inefficient use in compositions for cleaning and laundry, and their inefficient supply in fabrics, result in a very high cost, both for consumers and for the consumers. manufacturers of cleaning and laundry products. Therefore, the industry continues to urgently seek an efficient and effective mode of supply of fragrance in cleaning and laundry products, especially to improve the supply of durable fragrance to fabrics. One solution is to use vehicle mechanisms to deliver the perfume, for example by encapsulation. This is taught in the prior art and is described in the U.S. patent. No. 5,188,753. Another solution is to formulate compounds that provide a delayed release of the perfume over a longer period than that provided by using the perfume alone. A description of such compounds can be found in WO 95/04809, WO 95/08976 and in co-pending application EP 95303762.9. However, despite advances in the art, there is still a need for a compound that provides a delayed release of the active component, in particular a perfume ingredient.
This need is even more acute for perfume ingredients that are characteristic of fresh shades, particularly the perfume ingredients of the aldehyde and ketone type. Indeed, although these ingredients provide a fresh fragrance, these perfumes are also very volatile and have a low substantivity on the surface to be treated like the fabrics. Accordingly, a further object of the invention is to provide a softening composition comprising a perfume component that provides a fresh fragrance and is substantive to the treated surface. The applicant has now discovered that reaction products specific to amine-type compounds with an active aldehyde or ketone, such as imine-type compounds, also provide a delayed release of the active agent such as a perfume. Imine-type compounds are known in the art under the name of Schiff's bases, which are the condensation of an aldehyde perfume ingredient with an anthranilate. A typical description can be found in US 4853369. By means of this compound, the aldehyde perfume becomes substantive towards the fabrics. However, a problem encountered with these Schiff bases is that the methyl anthranilate compound also exhibits a strong odor, which results in a mixture of fragrances, reducing, and even inhibiting, the perception of the fragrance of aldehyde and / or ketone. In order to achieve said perfume composition with comparable fresh shades of aldehyde or ketone, which at the same time has satisfactory substantivity in the fabrics, the perfume formulators have formulated the composition on all sides. For example, having a vehicle or encapsulating material for such notes, for example with cyclodextrin, zeolites or starch. Another solution is the use of a glucosamine as described in
JP 09040687. However, it has been found that this compound gives very low stability in the washing process. As a result, an insufficient amount of perfume residue has been found on the fabric treated with these glucosamine-like compounds. Its use in softening compositions is not described. An additional solution is described in "Chemical release control", Kamogawa et al., J. Poly. Sci., Polym. Chem. Ed. Vol. 20, 3121 (1982), which describes the use of aminostyrene-type compounds condensed with aldehyde perfumes, whereby the release of the perfume is activated by copolymerization or acidification of the compound. However, its use is not mentioned. The applicant has now discovered that a reaction product between a specific primary and / or secondary amine and an active component also satisfies said need. Another advantage of the compounds of the invention is their ease of manufacture, which makes their use more convenient.
BRIEF DESCRIPTION OF THE INVENTION
The present invention relates to a reaction product between a primary and / or secondary amine compound and an active component selected from ketone, aldehyde, and mixtures thereof; characterized in that said amine-type compound has a lower Odor Intensity Index than that of a 1% methyl anthranilate solution in dipropylene glycol, and the reaction product has a Dry Surface Odor number of more than 5; and with the proviso that said amine-type compound is not an amino-styrene. In another aspect of the invention, there is provided a softening composition comprising a primary and / or secondary amine compound and an active component selected from ketone, aldehyde, and mixtures thereof; characterized in that said amine-type compound has an Odor Intensity Index lower than that of a 1% methyl anthranilate solution in dipropylene glycol. In a further aspect of the invention, there is provided a method for delivering residual fragrance to a surface, comprising the steps of contacting said surface with a compound or composition of the invention and thereafter contacting the treated fabric with a material so that the active ingredient is released from the reaction product between the amine and the active ingredient.
DETAILED DESCRIPTION OF THE INVENTION
The essential component of the invention is the reaction product between a primary and / or secondary amine compound and an active component selected from ketone, aldehyde, and mixtures thereof; characterized in that said amine-type compound has a lower Odor Intensity Index than that of a 1% methyl anthranilate solution in dipropylene glycol, and the reaction product has a Dry Surface Odor number of more than 5; and with the proviso that said amine-type compound is not an amino-styrene. When incorporated in the softening compositions, the reaction product is a reaction product between a primary and / or secondary amine compound and an active component selected from ketone, aldehyde, and mixtures thereof; characterized in that said amine-type compound has a lower Scent Intensity Index than that of a 1% methyl anthranilate solution in dipropylene glycol. Preferably, this compound has a Dry Surface Odor Index greater than 5.
I. Reaction product between a compound containing a primary and / or secondary amine functional group and a perfume component An essential component of the invention is a reaction product between a compound containing a primary and / or secondary amine functional group , and a perfume component, hereinafter referred to as "amine type reaction product".
A- Primary and / or secondary amine. By "primary and / or secondary amine" is meant a component carrying at least one primary and / or secondary amine and / or amide functional group. The primary and / or secondary amine type compound is also characterized by an Odor Intensity Index lower than that of a 1% methyl anthranilate solution in dipropylene glycol.
Odor Intensity Index Method By Odor Intensity Index it is understood that pure chemical substances were diluted 1% in dipropylene glycol, an odor-free solvent, used in perfumery. This percentage is more representative of the levels of use. Scent strips, or "teletas", were impregnated by immersion and presented to the expert panelist for evaluation. Expert panelists are trained counselors for at least six months in the qualification of odors and whose qualifications are reviewed for their accuracy and reproducibility against a reference on an ongoing basis. For each amine-type compound, two teletas were presented to the panelist: a reference (Me anthranilate, unknown to the panelists) and the sample. Panelists were asked to rank both strips for odor on an odor intensity scale of 0-5, with 0 for no detected odor and 5 for a very strong odor.
Results The following represents the Odor Intensity index of an amine-type compound suitable for use in the present invention and in accordance with the above procedure. In each case, the numbers are arithmetic averages among 5 expert panelists, and the results are statistically significantly different at 95% confidence level:
Methyl anthranilate 1% (reference) 3.4 Ethyl 4-aminobenzoate (EAB) 1% 0.9
A general structure for the primary amine compound of the invention is as follows: B- (NH 2) n; in which B is a vehicle material, and n is an index whose value is at least 1.
The compounds having a secondary amine group have a structure similar to the above, except that the compound comprises one or more -NH- groups in place of -NH2. In addition, the structure of the compound may also have one or more of both groups -NH2 and -NH-. Preferred B vehicles are inorganic or organic vehicles. By "inorganic vehicle" is meant a vehicle that does not have or substantially does not have carbon-based skeletons. Among the preferred inorganic vehicles are organic-organosilicon monomers or polymers or organosilane, siloxane, silazane, aluman, aluminosiloxane or aluminosilicate amino-derivatives. Typical examples of such vehicles are: organosiloxanes with at least one primary amine moiety such as the diaminoalkylsiloxane [H2NCH2 (CH3) 2Si] O, or the organoaminosilane (CeH5) 3SiNH2 described in "Chemistry and Technology of Silicone" of silicone], W. Noli, Academic Press Inc. 1998, London, p. 209, 106). Monomers or organic-organosilicon polymers or copolymers containing one or more portions of organosilylhydrazine are also preferred. A typical example of such a class of carrier material is N.N'-bisttrimetilsi? IOhydrazine (Me3Si) 2NNH2, described in "The OrganoSilicon Chemistry Second International Symposium, Puree and Applied Chemistry [Organosilicon Chemistry, Second International Symposium on Pure Chemistry and Applied], Vol. 19 Nos. 3-4 (1969) The following are also preferred mono- or polysilanes, exemplified by 1,1,1,3,3, 3-hexamethyl-2-phenylaminosyldildisilazane [(CH 3). 3Si] 2NSi (C6H5) NH2) 2, described in "OrganoSilicon Compounds", 1965, V. Bazant et al., Academic Press.) Other preferred examples of silicone polymer derivatives are 1, 1, 5 , 5,7,7,11, 11-octamethyl-3-9-bis [2- (2-aminoethylamino) -ethyl] -1, 5,7,11-tetrasyl-3,9-diaza-6,12- cyclic dioxacyclododecane and hexaethoxy-diamino-cyclo-tetrasiloxane (C6H5) (NH2) 2SÍ4 ?, ibidem, volume 2 part 2, page 474, page 454) Inorganic polymer carriers with amino functional groups to be used in the present invention are the polyaminoalkylpolysiloxanes. The typical description can be found in JP 79,131, 096, and EP 058 493. Even other inorganic polymer carriers suitable for use in the present invention are the polydialkylsiloxanes with amino functional groups described in EP 150 867, and having The general formula:
wherein R = C- ß alkyl, preferably C1-; n is an integer from 0 to 16, preferably from 1 to 6; R '= nothing, O, C = O, COO, NC = O, C = O-NR, NR, SOm, m = 2.3. Organic vehicles are vehicles that essentially have skeletons bonded with carbon. Typical amines having an organic carrier include aminoaryl-type derivatives, polyamines, amino acids and derivatives, substituted amines and amides, glucamines, dendrimers, and mono-, di-, oligo-, and amino-substituted polysaccharides. Of course, the amine compound may be interrupted or substituted with linkers or a substantive cellulose group. A general formula for this amine compound may be represented as follows: NH2n-Lm-B-Lm-R * m; wherein each m is an index whose value is 0 or at least 1, and n is an index whose value is at least 1 as defined above in the present invention. As can be seen above, the amino group is linked to a carrier molecule as defined by the classes described below. The primary and / or secondary amine group is linked directly to the vehicle group or via a linker group L. The vehicle may also be substituted with a substituent R *, and R * may be attached to the vehicle directly or via a linker group L Of course, R * may also contain branching groups, for example tertiary amine and amide groups. For the purposes of the invention, it is important that the amine-type compound, comprising at least one primary and / or secondary amine group, react with the aldehyde and / or ketone of the perfume to form the products of the reaction. Of course, the amine-type compound is not limited to having only one amine function. Indeed, and preferably, the amino compound comprises more than one amine function, thereby allowing the amine-type compound to react with various aldehydes and / or ketones. Accordingly, reaction products carrying aldehyde (s) and / or ketone (s) combined can be achieved, thereby resulting in a combined release of such fragrances. The typical linker group includes:
-N- - N - C - - (CH 2) X - I I II H R * O x > 0
substitution in the
L can also be a combination position or, m, p
L may also contain -O- if this group is not directly bonded to N, for example, H2N-CH2-CH2O- Most of the compounds described in the classes of amine-type compounds, will henceforth contain at least a substituent group classified as R *. R * contains from 1 to 22 carbon atoms in the main chain and optionally it can be an alkyl, alkenyl or alkyl benzene chain. It can also contain alicyclic, aromatic, heteroaromatic or heterocyclic systems, either inserted in the main chain or by substitution of an H atom of the main chain. In addition, R * can be attached to the vehicle material B or via a linker L, as defined above. In this case, L can also be -O-. The main chain can contain from 1 to 15 R * groups. Typical R * insertion groups include: - O- -C-O- -c- - O-C-O- - CH- II II, I or o or R *
H I - C-N - -N - - - C - II I I R R o OH OH NH O R * oH
-R * oH ^ C = N - and C = C '-CH2- CH2- O- - C3H6O R * oH R * oH
x = anion
the arrow indicates up to 3 substitutions in position 2, 3, 4.
R * may also contain several united insertion groups
each other, for example:
v. gr .: _CH2_CH2_oCH2_CH2_sc_ O In addition, R * can carry an E-end functional group that provides additional surface substantivity. Typical organic groups in this end group include:
R * O ll - OH, -OR * -NH ?, - N -C- N- R * or H I R *? H R *? H
H2-CH2-OH x "= anion of type CI", Br, S042_, etc ... O - C-OCH3-CH2-N + (CH3) 3 x "E can also be an aromatic, alicyclic, heteroaromatic or heterocyclic, including mono-, di-, oligo- and polysaccharides,
In addition, the R * groups can also be modified by substitution of one or more H atoms in the main chain. The substitution group can be E or the insertion groups defined above, wherein the insertion group is terminated with either H, E or R *. R * can also be a group made of ethoxy or epoxy groups with n ranging from 1 to 15, including groups such as: - (CH2CH20) n- H - (0-CH2CH2) n- OH
- (C3H60) n- H - (O-C 3H6) n-OH
As mentioned above, the preferred amine having organic carrier material B can be selected from aminoaryl derivatives, polyamines, amino acids and derivatives, substituted amines and amides, glucamines, dendrimers, mono-, di-, oligo- and amino-substituted polysaccharides. , and / or mixtures thereof.
1- Aminoaryl derivatives In this class of compounds, the amino group is preferably linked to a benzene ring. The benzene ring is further substituted in the para and / or meta position with R * as defined above. R * may be attached to the benzene ring by an L linker. The benzene ring may be substituted by other aromatic ring systems including naphthalene, idol, benzimidazole, pyrimidine, purine and mixtures thereof. Preferably, R * is attached to the benzene ring in its para position. Typical aminobenzene derivatives have the following formula: Preferred aminobenzene derivatives have the following formula:
Preferred aminobenzene derivatives are alkyl esters of 4-aminobenzoate type compounds, preferably selected from ethyl 4-aminobenzoate, phenylethyl 4-aminobenzoate, phenyl 4-aminobenzoate, 4-amino-N '- (3- aminopropyl) benzamide, and mixtures thereof.
2. Polyamines It is required that the polyamines of the invention have at least one free and unmodified primary and / or secondary amino group (preferably more than one), to react with the active aldehyde or ketone. In the polyamines, H may be substituted by R *, optionally by a linker group L. Additionally, the primary and / or secondary amine group may be attached to the polymer end by a linker group L. Suitable polyamine type compounds for to be used in the present invention are the polyamines soluble or water-dispersible. Typically, the polyamines to be used in the present invention have a molecular weight of between 150 and 2x106, preferably between 400 and 106, more preferred between 5000 and 106. These polyamines comprise skeletons which may be linear or cyclic. The polyamine backbones may also comprise polyamine branching chains to a greater or lesser degree. Preferably, the polyamine backbones described in the present invention are modified in such a way that at least one, preferably each nitrogen of the polyamine chain is described after said modification in terms of a unit that is substituted, quaternized, oxidized, or combinations thereof. For the purposes of the present invention, the term
"modification" as it refers to the chemical structure of polyamine, is defined as the replacement of a hydrogen atom of -NH of the skeleton with a unit R '(substitution), quatemization of a skeleton nitrogen (quaternization) or oxidation from a nitrogen of the skeleton to the N-oxide (oxidation). The terms "modification" and "substitution" are used interchangeably when reference is made to the process of replacing a hydrogen atom attached to a nitrogen of the backbone with a unit R '. The quaternization or oxidation may take place in some circumstances without substitution, but preferably the substitution is accompanied by oxidation or quaternization of at least one nitrogen of the skeleton. The linear or non-cyclic polyamine skeletons comprising the polyamine have the general formula: [R2N-R] n + 1 [N-R] m- [N-R] n-NR2. The cyclic polyamine skeletons comprising the polyamine have the general formula:
The above skeletons, prior to the subsequent optional but preferred modification, comprise primary, secondary and tertiary amine nitrogens linked by "linker" units R. For the purposes of the present invention, the primary amine nitrogens comprising the backbone or chain branch once modified, are defined as "terminal" units V or Z. For example, when a primary amine moiety, located at the end of the main backbone of the polyamine or branching chain, having the structure H2N- [R] - is modified from according to the present invention, it is hereinafter defined as a "terminal" V unit, or simply unit V. However, for the purposes of the present invention, some or all of the primary amine portions may remain unmodified, subject to the restrictions that are described here below. These unmodified primary amine portions, by virtue of their position in the skeleton chain, remain as "terminal" units. Similarly, when a portion of the primary amine, located at the end of the polyamine backbone, having the structure -NH2 is modified in accordance with the present invention, hereinafter it is defined as a "terminal" Z unit, or simply a unit Z. This unit may remain unmodified, subject to the restrictions described here below. Similarly, the secondary amine nitrogens comprising the backbone or branching chain, once modified, are defined as "backbone" units W. For example, when a secondary amine portion, the main constituent of the backbones and branch chains of the present invention, having the structure: H - [NR] -
, is modified according to the present invention, is then defined as a "skeleton" unit W, or simply a unit W. However, for the purposes of the present invention, some or all of the secondary amine portions may remain modified. These unmodified secondary amine portions, by virtue of their position in the skeleton chain, remain as "skeleton" units. In a similar manner, the tertiary amine nitrogens comprising the backbone or branching chain, once modified, are further referred to as "branching" Y units. For example when, a portion of tertiary amine, which is a chain branching point of the polyamine skeleton or other branching chains or rings, having the structure:
it is modified in accordance with the present invention, then it is defined as a "branching" Y unit or simply a Y unit. However, for the purposes of the present invention, some or all of the tertiary amine portions may remain unmodified. These unmodified tertiary amine portions, by virtue of their position in the skeleton chain, remain as "branching" units. The R units associated with the nitrogens of the units V, W and Y, which serve to bind the polyamine nitrogens, are described later in the present invention. The final modified structure of the polyamines of the present invention can therefore be represented by means of the general formula V (n + 1) WmYn Z for linear polyamine, and by the general formula V (n.k + 1) WmYnY'kZ for cyclic polyamine. For the case of polyamines comprising rings, a unit Y 'of the formula:
R [N-R] - serves as a branch point for a skeleton or branching ring. For each unit Y ', there exists a unit Y that has the formula:
[N-R] - which forms the point of attachment of the ring with the polymer backbone or branching. In the only case in which the skeleton is a complete ring, the polyamine skeleton has the formula: R i [RyM-R] ,. - [N-R] m- [N-R] n
therefore, it does not comprise terminal Z unit and has the formula: Vn-kWmYnY'k in which k is the number of branching units forming the ring. Preferably, the polyamine backbones of the present invention do not comprise rings. In the case of non-cyclic polyamines, the ratio of the index n to the index m, refers to the relative degree of branching. A fully linear unbranched modified polyamine according to the present invention has the formula: VWm Z that is, n is equal to 0. The larger the value of n (the smaller the proportion of man), the greater will be the degree of branching in the molecule. Typically, the value of m varies from a minimum value of 4 to 700, preferably 4 to 400, however, larger values of m are also preferred, especially when the value of the index n is very low or close to 0. Each polyamine nitrogen, whether primary, secondary or tertiary, once modified in accordance with the present invention, is subsequently defined as a member of one of three general classes; replaced, quaternized or oxidized. The unmodified polyamine nitrogen units are classified into units V, W, Y, Y 'or Z, depending on whether they are primary, secondary or tertiary nitrogens. That is, the unmodified primary amine nitrogens are V or Z units, the unmodified secondary amine nitrogens are units W or Y ', and the unmodified tertiary amine nitrogens are Y units, for the purposes of the present invention. Modified portions of primary amine are defined as "terminal" units V, and have one of three forms: a) simple substituted units that have the structure:
R-N- R I R b) quaternized units that have the structure:
R-N + -R I R in which X is an adequate counter-ion that provides charge balance; and c) oxidized units having the structure:
The modified secondary amine moieties are defined as "skeleton" units W having one of three forms: a) simple substituted units having the structure: - N- R - I R
b) quaternized units that have the structure:
R 'x- - N + -R - I R
in which X is an adequate counter-ion that provides a load balance; and c) oxidized units having the structure:
O t - N - R - I R Other modified secondary amine portions are defined as Y1 units that have one of three forms: a) simple substituted units having the structure:
- N- R - I R
b) quaternized units that have the structure:
R X "- N + - R - I R
wherein X is a suitable counter-ion to provide load balance; and c) oxidized units having the structure:
The modified tertiary amine moieties are defined as Y "branching" units having one of three forms: a) unmodified units having the structure:
- N- R -
b) quaternized units that have the structure:
in which X is an adequate counter-ion that provides a load balance; and c) oxidized units having the structure:
Certain portions of modified primary amine are defined as "terminal" Z units that have one of three forms: a) simple substituted units that have the structure:
- N- R I R
b) quaternized units that have the structure: R 'x- - N + - I R in which X is an adequate counter-ion that provides load balance; and c) oxidized units having the structure:
When any position on a nitrogen is not substituted or is not modified, it is understood that R 'will be substituted by hydrogen. For example, a primary amine unit comprising an R 'unit in the form of a hydroxyethyl portion is a V-terminal unit having the formula (HOCH2CH2) HN-.
For the purposes of the present invention, there are two types of chain terminator units, the V and Z units. The "terminal" Z unit is derived from a terminal primary amine portion of the structure -NH2- The non-cyclic polyamine skeletons according to the present invention, they comprise only one unit Z, while the cyclic polyamines may not comprise units Z. The unit "terminal" Z may be substituted with any of the units R 'described hereinafter, except when the Unit Z is modified to form an N-oxide. In the case where the nitrogen of unit Z is oxidized to an N-oxide, the nitrogen must be modified and therefore R 'can not be a hydrogen. The polyamines of the present invention comprise units
skeletal "linkers" R serving to join the nitrogen atoms of the skeleton. The R units comprise units which, for the purpose of the present invention, are called "hydrocarbon R" units and "oxy R" units. The "hydrocarbyl" units R are C 2 -C 12 alkylene, C 4 -C 2 alkenylene and C 3 -C 2 hydroxyalkylene, in which the hydroxyl portion can take any position on the chain of unit R, except the carbon atoms. carbon directly attached to the nitrogens of the polyamine skeleton; C-C 2 -dihydroxyalkylene wherein the hydroxyl portions can occupy any two of the carbon atoms of the chain of the R unit, except those carbon atoms directly attached to the nitrogens of the polyamine skeleton; dialkylarylene of C-8-C12 which, for the purpose of the present invention, are arylene portions having two alkyl substituent groups as part of the linker chain. For example, a dialkylarylene unit has the formula:
although the unit does not need to be 1, 4-substituted, but it can also be 1, 2- or 1, 3-substituted with C 2 -C 2 alkylene, preferably ethylene, 1,2-propylene and mixtures thereof , more preferred ethylene. The "oxy" R units comprise - (R1O) xR5 (OR1) x-, -CH2CH (OR2) CH2O) z (R0) and R1- (OCH2CH (OR2) CH2) w-, CH2CH (OR2) CH2-, - (R1O) xR1- and mixtures thereof. Preferred R units are C2-C-I2 alkylene, C3-C12 hydroxyalkylene, C4-C12 dihydroxyalkylene, C8-C2 dialkylarylene, - (R10) xR1-,
-CH2CH (OR2) CH2-, - (CH2CH (OH) CH2?) Z- (R1O) and R1 (OCH2CH- (OH) CH2) w-,
- (R1O) xR5 (OR1) x-; more preferred R units are C2-C2 alkylene, C3-C12 hydroxyalkylene, C-C2 dihydroxyalkylene, - (R10) xR1-, - (R1O) xR5 (OR1) x-, - (CH2CH (OH) CH2O ) z- (R1O) and R1 (OCH2CH- (OH) CH2) w-, and mixtures thereof, even more preferred R units are C2-C2 alkylene, C3 hydroxyalkylene, and mixtures thereof, being very preferred C2-C6 alkylene. The skeletons that are most preferred in the present invention comprise at least 50% of R units that are ethylene. The R1 units are C2-C6 alkylene, and mixtures thereof, preferably ethylene. R2 is hydrogen and - (R1O) xB, preferably hydrogen. R3 is C1-Cis alkyl, C -C2 arylalkylene, aryl substituted with C-C2 alkyl, C6-C2 aryl, and mixtures thereof, preferably C? -C alkyl? 2, C 7 -C 2 arylalkylene, more preferred C 1 -C 2 alkyl, more preferred methyl. The R3 units serve as part of the R 'units described below. R 4 is C 1 -C 2 alkylene, C 4 -C 2 alkenylene, arylalkylene
C8-C-? 2, arylene of C6-C? 0 > preferably C1-C10 alkylene, C8-C12 arylalkylene, more preferred C2-C8 alkylene, preferably ethylene or butylene. R5 is C1-C-12 alkylene, C3-C12 hydroxyalkylene, C-C12 dihydroxyalkylene, dialkylarylene of Cs-C2, -C (O) -, -C (O) NHR6NHC (O) -, -C ( 0) (R4) rC (O) -, R1 (OR1) -,
- (CH2CH (OH) CH2O (R1O) and R1OCH2CH (OH) CH2-, -C (O) (R4) rC (O) -,
- (CH2CH (OH) CH2-; R5 is preferably ethylene, -C (O) -, -C (O) NHR6NHC (O) -, -R1 (OR1) -, -CH2CH (OH) CH2-, - ( CH2CH (OH) CH2O (R1O) and R1OCH2CH- (OH) CH2-, more preferred -CH2CH (OH) CH2- .R6 is C2-C-12 alkylene or C6-C12 arylene The preferred R "oxy" units are further defined in terms of the units R1, R2 and R5 Preferred R "oxy" units comprise the preferred R1, R2 and R5 units The preferred polyamines of the present invention comprise at least 50% of R1 units which are ethylene. The preferred units R1, R2 and R5 are combined with the R "oxy" units to produce the preferred R "oxy" units in the following manner: i) substituting the preferred R5 units in
- (CH2CH2?) XR5 (OCH2CH2)? -, - (CH2CH20) xCH2CHOHCH2- (OCH2CH2) x- is produced. I) by substituting the preferred R1 and R2 in - (CH2CH (OR2) CH2O) z- (R10) and R1O (CH2CH (OR2) CH2) w-, - (CH2CH (OH) CH2O) z- (CH2CH2O) and CH2CH20 is produced (CH2CH (OH) CH2) w-. iii) by substituting the preferred R2 in -CH2CH (OR2) CH2-, -CH2CH (OH) CH2- is produced. The R 'units are selected from the group consisting of hydrogen, C? -C22 alkyl, C3-C22 alkenyl, C-C22 arylalkyl, C2-C22 hydroxyalkyl, - (CH2) pCO2M, - (CH2) qSO3M, -CH (CH2C? 2M) CO2M, - (CH2) pPO3M, - (R1O) mB, -C (O) R3, preferably hydrogen, C2-C22 hydroxyalkylene, benzyl, C? -C22 alkylene, - (R10) ) mB, -C (O) R3, - (CH2) pC02M,
- (CH2) qSO3M, -CH (CH2C02M) CO2M, more preferred C22 alkylene,
- (RO) xB, -C (O) R3, - (CH2) pCO2M, - (CH2) aSO3M, -CH (CH2CO2M) CO2M, preferably Ct-C22 alkylene, - (R1O) xB and -C (O ) R3. When no modification or substitution is made on a nitrogen, then the hydrogen atom will remain as the portion representing R. A highly preferred unit R 'is (R1O) xB. The units R 'do not comprise hydrogen atoms when the units V, W or Z are oxidized, that is, the nitrogens are N-oxides. For example, the skeleton chain or branch chains do not comprise units of the following structure:
O O O A - - R H - N - R - N - H I I H H H
Additionally, the R units do not comprise carbonyl moieties directly attached to a nitrogen atom when the units V, W or Z are oxidized, that is, the nitrogens are N-oxides. According to the present invention, the portion -C (O) R3 of the unit R 'is not bound to a nitrogen modified in N-oxide, that is, there is no N-oxide of amides having the structure:
or combinations thereof. B is hydrogen, C6 alkyl, - (CH2) qS03M, - (CH2) pC02M, - (CH2) q (CHSO3M) CH2SO3M, - (CH2) q (CHSO2M) CH2SO3M, - (CH2) pP03M, -PO3M, preferably hydrogen, - (CH2) qS03M,
- (CH2) q (CHSO3M) CH2SO3M, - (CH2) q (CHSO2M) CH2SO3M, more preferred hydrogen or - (CH2) qSO3M. M is hydrogen or a cation soluble in water in an amount sufficient to satisfy the charge balance. For example, a sodium cation also satisfies - (CH2) pCO2M and - (CH2) qSO3M, resulting in portions - (CH2) pCO2Na and - (CH2) qSO3Na. More than one monovalent cation (sodium, potassium, etc.) can be combined to satisfy the required chemical charge balance. However, the charge of more than one anionic group can be balanced by means of a divalent cation, or more than one monovalent cation may be necessary to satisfy the loading requirements of a polyanionic radical. For example, a - (CH2) pPO3M portion substituted with sodium atoms has the formula - (CH2) pPO3Na3. Divalent cations such as calcium (Ca2 +) or magnesium (Mg2 +) can be substituted by, or combined with, other suitable water-soluble monovalent cations. The preferred cations are sodium and potassium, and sodium is very preferred. X is a water-soluble anion such as chlorine (Cl "), bromine (Br) and iodine (I"), or X can be any negatively charged radical such as sulfate (SO42") and methosulfate (CH3SO3"). The indexes of the formulas have the following values: p has the value of 1 to 6, q has the value of 0 to 6; r has the value of 0 or 1; w has the value of 0 or 1, x has the value of 1 to 100; and has the value from 0 to 100; z has the value 0 or 1; m has the value from 2 to 700, preferably from 4 to 400, n has the value from 0 to 350, preferably from 0 to 200; m + n has the value of at least 5. Preferably x has a value that is in the range of 1 to 20, preferably 1 to 10. Preferred polyamines of the present invention comprise polyamine skeletons wherein about 50% of the R groups comprise "oxy" R units, preferably less than about 20%, more preferred less than 5%, and even more preferred the R units do not comprise "oxy" R units. Most preferred polyamines which do not comprise R "oxy" units, comprise polyamine skeletons in which less than 50% of the R groups comprise more than 3 carbon atoms. For example, ethylene, 1,2-propionate and 1,3-propylene comprise 3 or fewer carbon atoms and are the preferred "hydrocarbon" R units. That is, when the R units of the backbone are C2-C2 alkylene, C2-C3 alkylene is preferred and ethylene is most preferred. The polyamines of the present invention comprise homogenous and non-homogeneous modified polyamine backbones in which 100% or less of the -NH units are modified. For the purpose of the present invention, the term "homogeneous polyamine skeleton" is defined as a polyamine skeleton having the same R units (ie, all are ethylene). However, this definition of equality does not exclude polyamines comprising other foreign units comprising the polymer backbone, which are present due to an artifact of the chosen chemical synthesis method. For example, those skilled in the art know that ethanolamine can be used as an "initiator" in the synthesis of polyethyleneimines, therefore a polyethyleneimine sample comprising a hydroxyethyl portion resulting from the polymerization "primer" would be considered, comprising a homogeneous polyamine skeleton for the purposes of the present invention. A polyamine skeleton comprising all ethylene R units in which no Y branching units are present, is a homogeneous skeleton. A polyamine skeleton comprising all R units of ethylene is a homogeneous skeleton regardless of the degree of branching or the number of cyclic branches present. For the purposes of the present invention, the term
"non-homogeneous polymer skeleton" refers to polyamine skeletons which are a mixture of various lengths of unit R and types of unit R. For example, an inhomogeneous skeleton comprises R units which are a mixture of ethylene and 1,2-propylene units. For purposes of the present invention, a mixture of "hydrocarbyl" and "oxy" R units is not necessary to provide a non-homogeneous skeleton. The preferred polyamines of the present invention comprise homogeneous polyamine backbones which are fully or partially substituted with polyethyleneoxy moieties, total or partially quaternized amines, nitrogens totally or partially oxidized to N-oxides, and mixtures thereof. However, not all nitrogens of the amine skeleton should be modified in the same way, leaving the choice of modification to the specific needs of the formulator. The degree of ethoxylation is also determined by the specific requirements of the formulator. Preferred polyamines comprising the backbone of the compounds of the present invention are generally polyalkylene imines (PAI's), polyethylene imines (PEI's), or PEI's joined in portions having longer R units than the PAI's, or original PEI's. Preferred amine polymer backbones comprise R units which are C2 alkylene units (ethylene), also known as polyethylene amines (PEI's). Preferred PEI's have at least moderate branching, that is, the ratio of m to n is less than 4: 1, however, PEI's that have a ratio of m to n of 2: 1 are more preferred. Preferred skeletons, before modification, have the general formula: R 'I i I [R2NCHCH2] n - [NCH2CH2] m- [NCH2CH2] n- NR2 in which R, m and n are the same defined above. Preferred PEI's will have a molecular weight of more than 200 daltons. The relative proportions of the primary, secondary and tertiary amine units in the polymer backbone, especially in the case of PEI's, will vary, depending on the form of preparation. Each hydrogen atom attached to each nitrogen atom of the polyamine backbone chain represents a potential site for subsequent substitution, quaternization or oxidation. These polyamines can be prepared, for example, by polymerizing ethyleneimine in the presence of a catalyst such as carbon dioxide, sodium bisulfite, sulfuric acid, hydrogen peroxide, hydrochloric acid, acetic acid, etc. The specific methods for preparing these polyamine skeletons are described in the U.S. patent. No. 2,182,306, Ulrich et al., Issued December 5, 1939; the patent of E.U.A. Do not.
3,033,746, Mayle et al., Issued May 8, 1962; the patent of E.U.A. No. 2,208,095, Esselman et al., Issued July 16, 1940; the patent of E.U.A. No. 2,806,839, Crowther, issued September 17, 1957; and the patent of E.U.A. No. 2,553,696, Wilson, issued May 21, 1951; all incorporated in the present invention as reference. Preferred polyamines are polyethyleneimines commercially available under the trademark Lupasol such as Lupasol FG (MW 800), G20wfv (MW 1300), PR8515 (PM 2000), WF (PM 25000), FC (MW 800), G20 (PM 1300), G35 (PM 1200), G100 (PM 2000), HF (PM 25000), P (PM 750000), PS (PM 750000), SK (MW 2,000,000), SNA (MW 1, 000,000). Other polyamines suitable for use in the present invention are poly [oxo (methyl-1,2-ethanediyl)], a- (2-aminomethylethyl) - [beta] (2-aminomethyl-ethoxy) (= CAS No. 9046-10 -0); poly [oxy (methyl-1,2-ethanediyl)], α-hydro) -? - (2-aminomethylethoxy) -, ether with 2-ethyl-2- (hydroxymethyl) -1,3-propanediol (= CAS No 39423-51-3); commercially available under the brand name of Jeffamines T-403, D-230, D-400, D-2000; 2,2,2,2-diamino-diethylamine, 3,3'-diamino dipropylamine, 1,3-bis-aminoethyl-cyclohexane, commercially available from Mitsibushi, and 2,2,2,2,2-diamino-diethylamine; the commercially available Stemamines C- | 2 of Clariant such as Stemamin (propylenamine) n C12 with n = 3/4, and mixtures thereof.
3- Amino Acids and Derivatives Other suitable compounds to be used in the present invention are amino acids and their derivatives, especially the ester and amide derivatives. The most preferred compounds are those that provide improved surface substantivity because of their structural characteristic. For clarity, the term amino acids and their derivatives does not encompass polymeric compounds. Suitable amino acids have the following functionality of formula:
in which Ri = H, R * or (L) -R *, and R is the amino acid side group, generally referred to as the "R group" as in "Principies of Biochemistry" by Lehninger and others , 1997, second edition, Worth, pages 114-116. Preferred amino acids for use in the present invention are selected from tyrosine, tryptophan, lysine, glutamic acid, glutamine, aspartic acid, arginine, asparagine, phenylalanine, proline, glycine, serine, histidine, threonine, methionine and mixtures thereof, preferably they are selected from tyrosine, tryptophan and mixtures thereof. Other preferred compounds are the amino acid derivatives selected from tyrosine ethylate, glycine methylate, tryptophan ethylate, and mixtures thereof.
4. Substituted amines and amides For clarity, the term substituted amines and amides does not encompass polymeric compounds. The substituted amine and amide compounds suitable for use in the present invention have the following general formula: NH2-L-R **, wherein L is -CO- in the case of an amide. Another optional linker group can be as defined under R *. R ** is as defined here above under R *, with the proviso that it contains at least 6 carbon atoms and / or N atoms and / or cyclohexyl-, piperidine, piperazine and other heterocyclic groups such as:
(L1, NH2) x
Optionally, H in NH can be replaced by R *. Preferred substituted amines and amides for use in the present invention are selected from nipecotamide, N-coco-1, 3-propendiamine, N-oleyl-1,3-propendiamine, N- (tallowalkyl) -1, 3-propendiamine, 1,4-diamino-cyclohexane, 1,2-diamino-cyclohexane, 1,1-diaminododecane, and mixtures thereof.
. Glucamines A further preferred class of amine compounds is the class of glucamines of general structure: NH2-CH2- (CH (OH)) x-CH2OH in which one or more OH functions may be substituted, preferably by -OR *, and wherein x is an integer whose value is 3 or 4. R * can be attached to the OH groups either directly or by means of a linker unit as mentioned above in the present invention under L. For clarity, the term glucamine does not cover polymeric compounds. Preferred compounds of this class are selected from 2,3,4, 5,6-pentamethoxy-glucamine, 6-acetylglucamine, glucamine, and mixtures thereof.
6. Dendrimers Another additional class of amine compounds is the class of dendrimers. Suitable dendrimers carry free primary amine groups at the periphery of the spherical molecules, which can react with aldehydes or ketones (perfumes) to form the desired amine reaction product (perfume component) of the invention. By dendrimers it is meant that the molecule is formed from a core molecule as described for example in WO 96/02588, and in "Synthesis" [Synthesis], Feb. 1978, pages 155-158, or in " Encyclopedia of Polymer Science &Engineering "[Encyclopedia of Polymer Science and Engineering], 2nd. edition, Hedstrand and others, in particular pages 46-91. The core is typically attached to multifunctional components to form the "generations." For the purposes of the present invention, the nature of internal generations is not critical. They can be based, for example, on polyamidoamines, polyamido alcohols, polyethers, polyamides, polyethylene imines, etc. It is important for the purposes of the present invention that the external generation (s) contain accessible primary and / or secondary amino functions. Also suitable are glycodendrimers such as those described for example in Nachrichten aus Chemie 11 (1996) p 1073-1079 and in WO 97/48711, with the proviso that free primary and / or secondary amine groups are present in the surface of these molecules. Preferred compounds are the polyethylenimine and polypropyleneimine dendrimers, the commercially available dendrimers of polyamidoamines (PAMAM) Starburst®, G0-G10 generation of Dendritech, and the Astromols® dendrimers, generation 1-5 of DSM being DiAminoButane polyamine DAB (PA) dendrimers with x = 2nx4 and n being generally comprised between 0 and 4.
7. Mono-, di-, oligo- and polysaccharides substituted with amino For the purposes of the present invention, the specific amino-substituted mono-, di-, oligo- and polysaccharides are also suitable. For the amino substituted monosaccharide of the present invention, it is necessary that the hemi-acetal and / or hemyl ketal functional group be blocked by a suitable substituent to provide sufficient stability for the intended application. As indicated above in the present invention, glucosamine is not a suitable amine. However, if the hemiacetal OH function is replaced by R *, said monosaccharide is made suitable for the purposes of the present invention. The amino group may be in the 2 to 5 or 6 position, depending on the type of monosaccharide, and is preferably in the C2, C5 or C6 position. Suitable amino substituted monosaccharides are: - C5 aldoses / ketoses: ribose, arabinose, xylose, lyxose, ribulose, xylulose; - C6 aldoses / ketoses: allose, altrose, glucose, mannose, gulose, galactose, talose, fructose, sorbose, tagatose, psychosis.
For amino-substituted disaccharides with unsubstituted aldose or ketose groups, the free OH-group needs to be replaced by R *, for example in lactose and maltose, while in sucrose there is no free acetal / ketal OH group. Optionally, more than one OH group can be substituted for R *. Suitable amino-substituted disaccharides are amino-substituted lactose, maltose, sucrose, cellobiose and trehalose. Suitable oligo- and polysaccharide-substituted amino polysaccharides are starch, cyclodextrin, dextran, glycogen, cellulose, mannan, geran, levane, alternating glucose, mannose, galactose, fructose, lactose, maltose, sucrose, cellobiose, cyclodextrin, chitosan, and / or mixtures thereof, amino-substituted. The molecules require carrying at least one amino group, preferably several. Chitosan does not require additional amino substitution. Also suitable for coupling carboxyl or aldehyde containing compounds are the following oligo- and functionalized polysaccharides and glycans, commercially available from the company Carbomer. In brackets is the reference number of Carbomer: Aminoalginate (5, 00002), diamnoalginate (5.00003), hexanediaminalgiene (5.00004 - 5.00006 - 5.00008), dodecanediaminalginate (5.00005 - 5.00007 - 5.00009), 6-amino-6-deoxy cellulose (5 , 00020), O-ethylaminocellulose (5,00022), O-methylaminocellulose (5,00023), 3-amino-3-deoxycellulose (5,0024), 2-amino-2-deoxycellulose (5,00025), 2,3 -diamino-2,3-dideoxycellulose (5,00026), 6 [N- (1,6-hexanediamine)] - 6-deoxy-cellulose (5,00027), 6- [N- (1,12-docedanodiamin)] - 6-deoxycellulose (5,00028), 0- [methyl- (N-1, 6-hexandiamin)] cellulose (5,00029), O- [methyl- (N-1, 12-dodecandiamin)] cellulose (5, 00031), 2,3-diamino-2,3-deoxy-alpha-cyclodextrin (5,0053), 6-amino-6-deoxy-beta-cyclodextrin (5,00054), O-ethylamino-beta-cyclodextrin (5, 0055), 6 [N-1, 6-hexandiamin) -6-deoxy-alpha-cyclodextrin (5,00056), 6 [N-1, 6-hexandiamin) -6-deoxy-beta-cyclodextrin (5,00057) , Aminodextran (5,00060), N- [di- (1,6-hexanediamine)] dextran (5,00061), N- [di- (1, 12-dodecandiamin)] dextran (5.0062), 6- amino-6-deoxy-alpha-D-galactosyl-guarano (5,00070 ), O-ethylaminoglorane (5,00071), Diaminoguarane (5,00072), 6-amino-6-deoxy-starch (5,00080), O-ethyl-starch (5,00081), 2,3-diamine-2, 3-dideoxyamide (5,00082), N- [6- (1,6-hexanediamine)] - 6-deoxydistamide (5,00083), N- [6- (1,12-dodecanediamine)] - 6-Deoxystarch (5,00084) and 2,3-di- [N (1,6-hexane diamine)] - 2,3-dideoxystarch (5,00085). In addition, with the use of any of the aforementioned compounds comprising at least one primary and / or secondary amine group such as polyamine, the resulting amine reaction product will provide fabric appearance benefits, in particular color care. and protection against fabric wear. Indeed, the appearance of the fabrics, for example of clothing, bedding, domestic clothing such as table linen, is a matter of interest to consumers. In effect, after the typical uses of the fabrics by the consumer, such as use, washing, rinsing and / or drying in the dryer, a loss of the original appearance of the fabric is observed, which may be partly due to the loss of fidelity and definition of color. Said problem of color loss is even more acute after multiple washing cycles. It has been found that the compositions of the present invention provide improved fabric appearance, protection against fabric wear and improved color care to washed fabrics, especially after multiple wash cycles. Therefore, the compositions of the present invention can simultaneously provide fabric care benefits and long-lasting perfume benefits.
B- Ketone v / o active aldehyde. Preferably, for the aforementioned compounds, active ketone or active aldehyde is understood to be any chain containing at least 1 carbon atom, preferably at least 5 carbon atoms. Preferably, the active ketone or the active aldehyde are respectively selected from a ketone or aldehyde flavoring ingredient, a ketone or aldehyde type pharmaceutical active ingredient, an agent for ketone or aldehyde biological control, a perfume component of ketone or aldehyde type, a ketone or aldehyde-type cooling agent and mixtures thereof. Flavoring ingredients include spices, flavor enhancers that contribute to the overall perception of flavor. The pharmaceutical active ingredients include drugs.
Agents for biological control include biocides, antimicrobials, bactericides, fungicides, algaecides, mildew, disinfectants, antiseptics, insecticides, vermicides, plant growth hormones. Agents for biological control include biocides, antimicrobials, bactericides, fungicides, algicides, mildew, disinfectants, sanitizing agents such as chlorine, antiseptics, insecticides, insect repellents and / or moths, vermicides, plant growth hormones. Typical antimicrobials include glutaraldehyde, cinnamaldehyde and mixtures thereof. Repellents for insects and / or moths are perfume ingredients, such as citronellal, citral, N, N-diethyl-meta-toluamide, Rotundial, 8-acetoxycarvotanacenone, and mixtures thereof. Other examples of repellents for insects and / or moths to be used in the present invention are described in the patents E.U.A. Nos. 4,449,987, 4,693,890, 4,696,676, 4,933,371, 5,030,660, 5,196,200 and in "Semi Activity of Flavor and Fragrance Molecules on various Insect Species" ["Semi-Activity of Flavor and Fragrance Molecules on Various Insect Species"], B.D. Mookherjee et al., Published in Bioactive Volatile Compounds from Plants, ACS Symposium Series 525 [Biologically Active Volatile Compounds from Plants, Symposium Series of the American Chemical Society], R. Teranishi, R.G. Buttery and H. Sugisawa, 1996, pp. 35-48.
A typical description of suitable ketones and / or aldehydes traditionally used in perfumery can be found in "Perfume and Flavor Chemicals", vol. I and II, S. Arctander, Allured Publishing, 1994, ISBN 0-931710-35-5. Perfume ketone-type components include components that have odoriferous properties. Preferably, for the aforementioned compounds, the perfume ketone is selected by its characteristic bucoxime odor; isojasmone; methyl-beta-naphthyl ketone; Musk ndanona; tonalid / musk plus; Alpha-Damascone, Beta-Damascone, Delta-Damascone, Iso-Damascone, Damascenone, Damask, Methyl-Dihydrojasmonate, Mentone, Carvone, Camphor, Fenchone, Alpha-lonone, Beta-lonone, Lonona Denominated Gamma-Methyl, Fleuramone, Dihydrojasmone, Cís-Jasmona, Iso-E-Super, Methyl-Cedrenil-Cetona or Methyl-Cedrilona, Acetophenone, Methyl-Acetophenone, Para-Methoxy-Acetophenone, Methyl-Beta-Naphthyl-Ketone, Benzyl-Acetone, Benzophenone, Para-Hydroxy- Phenyl-Butanone, celery ketone or Livescone, 6-lsopropyldehydro-2-naphthone, Dimethyl-Octenone, Freskomenta, 4- (1-Ethoxyvinyl) -3,3,5, 5, -Tetramethyl-Cyclohexanone, Methyl-Heptenone, 2 - (2- (4-MetiI-3-cyclohexen-1-yl) propyl) -cyclopentanone, 1- (p-Menten-6 (2) -yl) -1-propanone, 4- (4-Hydroxy) 3-methoxyphenyl) -2-butanone, 2-Acetyl-3,3-Dimethyl-Norbomann, 6,7-Dihydro-1,1, 2,3,3-Pentamethyl-4 (5H) -nndanone, 4-Damascol, Dulcinil or Cassiona, Gelsona, Hexalon, Isociclemone E, Methyl Cyclocitrona, Methyl-Lavender-Ketone, Orívon, Para-Ter-Butyl-Cyclohexanone, Verdone, Delphona, Muscona, Neobutenone, Plicatona, Veloutone, 2,4,4,7-Tetramethyl-oct-6-en-3-one, Tetrameran. Preferably, for the aforementioned compounds, the preferred ketones are selected from alpha-damascone, delta-damascone, iso-damascone, carvone, gamma-methyl-ionone, Iso-E-Super, 2,4,4,7-tetramethyl-oct-6-en-3 -one, benzylacetone, beta-damascone, damascenone, methyl dihydrojasmonate, methyl cedrilone, and mixtures thereof. The aldehyde-like components of perfumes include components having odoriferous properties. Preferably, for the aforementioned compounds, the perfume aldehyde is selected by its characteristic odor of adoxal; anisic aldehyde; cimal; ethyl vanillin; florhidral; helional; heliotropin; Hydroxycitronella; koavona; lauric aldehyde; liral; methylnonylacetaldehyde; P. bucinal; phenylacetaldehyde; undecylenic aldehyde; vanillin; 2,6,10-trimethyl-9-undecenal, 3-dodecen-1-al, alpha-n-amylcinnamic aldehyde, 4-methoxybenzaldehyde, benzaldehyde, 3- (4-tert-butylphenyl) -propanal, 2-methyl-3 - (para-methoxy-phenyl) -propanal, 2-methyl-4- (2,6,6-trimethyl-2 (1) -cyclohexen-1-yl) butanal, 3-phenyl-2-propenal, cis- / trans 3,7-dimethyl-2,6-octad-in-1-al, 3,7-dimethyl-6-octen-1 -al, [(3,7-dimethyl-6-octenyl) oxy] acetaldehyde, 4 -isopropylbenzaldehyde, 1, 2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthaldehyde,
2,4-dimethyl-3-cyclohexen-1-carboxaldehyde, 2-methyl-3- (isoplphenyl) pnal,
1-decanal; decylaldehyde, 2,6-dimethyl-5-heptenal, 4- (tricyclo [5.2.1.0 (2,6)] - decidium-8) -butanal, octahydro-4,7-methano-1 H-indencarboxaldehyde, 3 -ethoxy-4-hydroxy benzaldehyde, para-ethyl-alpha, alpha-dimethyl-hydrocinnamaldehyde, alpha-methyl-3,4- (methylenedioxy) -hydrocinnamaldehyde, 3,4-methylenedioxybenzaldehyde, alpha-n-hexyl cinnamic aldehyde, -cime-7-carboxaldehyde, alpha-methylphenylacetaldehyde, 7-hydroxy-3,7-dimethyloctanal, Undecenal, 2,4,6-trimethyl-3-cyclohexen-1 -carboxaldehyde, 4- (3) (4-methyl-3 -pentenyl) -3-cyclohexen-carboxaldehyde, 1-dodecanal, 2,4-dimethylcyclohexen-3-carboxaldehyde, 4- (4-hydroxy-4-methylpentyl) -3-cyclohexen-1 -carboxaldehyde, 7-methoxy-3, 7-dimethyloctan-1-al, 2-methylundecanal, 2-methyldecanal, 1-nonanal, 1-octanal, 2,6,10-trimethyl-5,9-undecadienal, 2-methyl-3- (4-terbutyl) pnal , dihydrocinnamic aldehyde, 1-methyl-4- (4-methyl-3-pentenyl) -3-cyclohexen-1 -carboxaldehyde, 5 or 6-methoxy-Hexahydro-4,7-methanoindan-1 or 2-carboxaldehyde, 3,7-dimethyloctan -1-al, 1-undecanal, 10-undecen-1-al, 4-hydroxy-3-methoxybenzaldehyde, 1-methyl-3- (4-methylpentyl) -3-cyclohexene-carboxaldehyde, 7-hydroxy-3,7-dimethyl-octanal, trans-4- decenal, 2,6-nonadienal, para-tolylacetaldehyde; 4-methylphenylacetaldehyde, 2-methyl-4- (2,6,6-trimethyl-1-cyclohexen-1-yl) -2-butenal, ortho-methoxycinnamic aldehyde, 3,5,6-trimethyl-3 -cyclohexencarboxaldehyde, 3,7-dimethyl-2-methylene-6-octenal, phenoxyacetaldehyde, 5,9-dimethyl-4,8-decadienal, peony aldehyde (6,10-dimethyl-3-oxa-5,9-undecadien -1-al), hexahydro-4,7-methanoindan-1 -carboxyaldehyde, 2-methyloctanal, alpha-methyl-4- (1-methylethyl) benzeneacetaldehyde, 6,6-dimethyl-2-norpinen-2-ponaldehyde, -methyl-phenoxyacetaldehyde, 2-methyl-3-phenyl-2-pn-1-a, 3,5,5-trimethylhexanal, Hexahydro-8,8-dimethyl-2-naphthaldehyde, 3-pl-bicyclo [2.2 .1] -hept-5-en-2-carbaldehyde, 9-decane, 3-methyl-5-phenyl-1-pentanal, methylene-acetaldehyde, hexanal, trans-2-hexanal, 1-p-mentho-q-carboxaldehyde, and mixtures thereof. The most preferred aldehydes are selected from 1 -decanal, benzaldehyde, florhydral, 2,4-dimethyl-3-cyclohexen-1 -carboxaldehyde; cis / trans-3,7-dimethyl-2,6-octadien-1 -al; heliotn; 2,4,6-trimethyl-3-cyclohexen-1-carboxaldehyde; 2,6-nonadienal; alpha-n-amylcinnamic aldehyde, alpha-n-hexyl cinnamic aldehyde, P.T. Bucinal, liral, cimal, methyl-nonyl-acetaldehyde, hexanal, trans-2-hexenal, and mixtures thereof. In the above list of perfume ingredients, some are commercial names conventionally known to those skilled in the art and also include isomers. Said isomers are also suitable for use in the present invention. In another embodiment, for the purposes of the present invention, perfume compounds are preferably suitable, preferably active ketones or aldehydes of perfumes characterized by having a low Odor Detection Threshold. Said Odor Detection Threshold (ODT) should be less than or equal to 1 ppm, preferably less than or equal to 10 ppb -measured under controlled Gas Chromatography (GC) conditions such as those described below in the present invention. This parameter refers to the value commonly used in the perfumery techniques and which is the lowest concentration at which significant detection of some odorous present material takes place. See for example "Compilation of Odor and Taste Theshold Valué Data" [Compilation of Odor and Flavor Threshold Values] (ASTM DS 48A), edited by F.A. Fazzalari, International Business Machines, Hopwell Junction, New York, and Calkin and others, "Perfumery, Practice and Principies", John Wiley & Sons, Inc. page 243 et seq. (1994). For the purposes of the present invention, the Odor Detection Threshold is measured according to the following method: The gas chromatograph is characterized to determine the exact volume of material injected by the syringe, the precise separation ratio, and the hydrocarbon response using a hydrocarbon standard of known concentration and chain length distribution. The air flow velocity is exactly measured, and the volume sampled is calculated assuming that the duration of a human inhalation is 0.02 minutes. As it is known the precise concentration in the detector at any point of time, we know the mass by volume inhaled and therefore the concentration of material. To determine the ODT of a perfume material, solutions are provided in the sniffing portal at the recalculated concentration. A panelist sniffs the effluent from the GC and identifies the retention time when he perceives the odor. The average of all the panelists determines the perception threshold. The necessary amount of analyte is injected into the column to reach a certain concentration in the detector, for example 10 ppb. The typical parameters of the gas chromatograph are then annotated to determine the odor detection thresholds. GC: 5890 Series II with FID detector, Autosampler 7673 Column: J &; W Scientific DB-1, 30 meters long, Dl 0.25 mm, film thickness of 1 miera. Method: Separation injection: Separation ratio 17/1 Autosampler: 1.13 microliters per injection. Flow of the column: 1.10 ml / minute. Air flow: 345 ml / minute. Entry temperature: 245 ° C. Detector temperature: 285 ° C. Temperature information: Initial temperature: 50 ° C. Speed: 5 ° C / minute. Final temperature: 280 ° C. Final time: 6 minutes. Load assumptions: 0.02 minutes per sniff. GC air is added to the dilution of the sample.
Examples of preferred perfume components are selected from: 2-methyl-2- (para-iso-propylphenyl) propionaldehyde, 1- (2,6,6-trimethyl-2-cyclohexan-1-yl) -2-buten- 1-one and / or para-methoxy-acetophenone. Most preferred are the following compounds that have an ODT < 10 ppb, measured by the method described above: undecylenic aldehyde, gamma-undecalactone, heliotropin, gamma-dodecalactone, p-anisic aldehyde, para-hydroxy-phenyl-butanone, cimary, benzylacetone, alpha-ionone, p.t. bucinal, damascenone, beta-ionone and metl-nonyl-ketone. Typically, the level of active agents is from 10 to 90%, preferably from 30 to 85%, more preferred from 45 to 80% by weight of the amine reaction product. Preferred amine-type reaction products are those that originate from the reaction of polyethyleneimine polymer as Lupasol polymers, with one or more of the following: Alpha-Damascone, Delta-Damascone, Carvona, Hedione, Florhidral, Lilial, Heliotropin, Gamma-Methyl-lonone and 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde. Other preferred amine reaction products are those that originate from the reaction of Astramol dendrimers with carvone, as well as those that originate from the reaction of ethyl 4-aminobenzoate with 2,4-dimethyl-3-cyclohexen-1. -carboxaldehyde. The most preferred reaction products of amine are those of the reaction of Lupasol HF with delta-damascone; Lupasol G35 with alpha-damascone; Lupasol G100 with 2,4-dimethyl-3-cyclohexen-1 -carboxaldehyde, ethyl 4-amine-benzoate with 2,4-dimethyl-3-cyclohexen-1 -carboxaldehyde.
Procedure The preparation of the component is done as follows in the synthesis examples. In general, the nitrogen analogs of ketones and aldehydes are called azomethins, Schiff's bases or the preferred name of mines. These imines can be easily prepared by condensation of primary amines and carbonyl compounds by removal of water. A typical reaction profile is as follows:
O OH I R "'R' H2N- R" R- C- NH- R "I R
The ß-unsaturated ketones not only condense with amines to form imines, but they can also undergo an addition 1, 4
competitive to form ß-amino ketones.
By means of this simple method, a compound and composition containing said compound are made which achieve a delayed release of the active ingredient. As can be seen, the perfume ingredient is typically present in an equimolar amount to the amine function, in order to allow the reaction to take place and provide the resulting amine reaction product. Of course, a larger amount is not excluded, and it is even preferred when the amine compound comprises more than one amine function. When the amine compound has more than one primary and / or secondary amine group, several different perfume raw materials may be attached to the amine compound.
Release Mechanism By means of the present invention, a delayed release of a perfume ingredient, ie, ketone or aldehyde, is obtained. Without being limited by theory, it is believed that the release occurs by the following mechanisms: For the imine compounds, the perfume components are released upon the breakdown of the mine bond, leading to the release of the perfume component and the primary amine compound . This can be achieved by hydrolysis, photochemical dissociation, oxidative dissociation or enzymatic dissociation. For ß-amino ketone compounds, the treatment with the humidity of the air and / or the water, accurately releases the perfume component and the amine compound. However, other means of release such as hydrolysis, photochemical dissociation, oxidative dissociation or enzymatic dissociation are not excluded. Other release means can be considered for the imine and ß-amino ketone compounds, such as the vaporization step of the ironing of the treated fabric, drying in a dryer and / or use.
Application Compositions Application compositions of the present invention include compositions in which there is a need for delayed release of an active ketone or aldehyde. These include rinse-off compositions such as softener compositions, personal care compositions such as shower gels, deodorants, bars, shampoos.; independent compositions such as deodorant compositions, insecticidal compositions, etc. Preferred are those compositions that result in the compound of the invention coming into contact with the fabric. The compositions of the invention are suitable for use in any of the domestic treatment steps, ie as a composition for pre-treatment and / or post-treatment, as a washing additive, as a composition suitable for use in the rinse process. Of course, multiple applications can be made such as treating the fabric with a composition of the invention for pre-treatment and thereafter with the appropriate composition to be used in the rinsing process and / or in the drying process. With the phrase "compositions suitable for use in the rinsing process," it should be understood that this includes compositions such as fabric softening compositions that are added in the rinse and aggregate compositions in the dryer (eg, sheets) which provide smoothing benefits and / or antistatic, as well as additives for rinsing. Preferred are those compositions that result in the compound of the invention coming into contact with the fabric. It should be understood that these include compositions such as fabric softener compositions that are added in the rinse and aggregate compositions in the dryer (eg, sheets) which provide softening and / or antistatic benefits. Preferably, the amine reaction product (s) that are incorporated in said cleaning and laundry compositions, provide a dry surface Odor Index of more than 5, preferably at least 10. By Odor Index on Dry Surface it is understood that the amine reaction product or products provide a delta of more than 5, where delta is the difference between the Odor Index of the treated dry surface with the amine reaction product (s), and the Odor Index of the dry surface treated only with the perfume raw material.
Method of measuring the Odor Index on the dry surface for the surface of the cloth Preparation of the product: The reaction product of amine is added to the non-scented product base. The base of the non-perfumed product is as follows, wherein the abbreviations are as defined below in the present invention for the examples:
The levels of the amine reaction product are selected in such a way as to obtain an odor grade on the dry cloth of at least 20. After mixing carefully stirring the container in case of being liquid, or with spatula in case of being powder , the product is left to rest for 24 hours.
Washing procedure: The resulting product is added to the washing machine at the dose and in the dispenser that are appropriate for its category. The quantity corresponds to the recommended doses made for the corresponding commercial products: typically between 70 and 150 g of a detergent powder or liquid by means of a common dosing device such as a granule or arielete, and between 25 and 40 ml for a liquid fabric softener. The load is composed of four bath towels (170 g) using a Miele W830 washing machine in short wash cycle at 40 ° C, water inlet: 15 ° hardness at a temperature of 10-18 ° C, and full rotation of 1200 rpm. The same procedure was applied for the corresponding free perfume ingredient under consideration, and was used as the reference. Dosages, clothing loads and wash cycles were identical for the reference and the sample.
Drying procedure: In the course of two hours after the end of the washing cycle, the odors of the fabrics were determined after the rotation drying cycle, but still wet, using the scale mentioned below. Subsequently, half of the pieces of cloth are hung on a rope for 24 hours for drying, away from possible contamination. Unless specified, this drying takes place indoors. The environmental conditions are at temperature between 18 and 25 ° C and air humidity between 50 and 80%. The other half is placed in a rotary dryer and subjected to a complete cycle of "very dry", that is, in a Miele Novotronic T430 placed in the dry-extra-white program (complete cycle). The fabrics dried in this dryer are also tested the next day. The fabrics are then stored in open aluminum bags, in a room free of odors, and tested again after 7 days.
Odor assessments: The smell is determined by expert panelists smelling the fabrics carefully. A scale of 0-100 is used for all fabric odor ratings. The rating scale is as follows: 100 = extremely strong perfume smell. 75 = perfume smell very strong. 50 = strong smell. 40 = moderate smell of perfume. 30 = light smell of perfume. 20 = weak smell of perfume. 10 = very weak smell of perfume. 0 = no smell.
A difference of more than 5 degrees after one day and / or 7 days between the reaction product of amine and the perfume raw material is statistically significant. A difference of 10 degrees or more after a day and / or 7 days, represents an inclined change. In other words, when a difference of more than 5 degrees, preferably at least 10, is observed between the amine reaction product and the perfume raw material, after 1 day or 7 days, or both, 1 day and 7 days, it can be concluded that the amine reaction product is suitable for use in the present invention, provided that the amine compound complies with the Odor Intensity index. The amine reaction product as defined above in the present invention is comprised from 0.0001% to 10%, preferably from 0.001% to 5%, and more preferred from 0.01% to 2% by weight of the composition. Mixtures of the compounds in the present invention can also be used. If necessary, the incorporation of the amine reaction product in the cleaning and laundry compositions can be conveniently carried out by the conventional means of incorporation., such as aspersion, encapsulation such as encapsulation with starch, for example as described in GB 1464616, dry addition, or by encapsulation in cyclodextrin. Preferably, the amine reaction product is preformed prior to incorporation into the compositiof the invention. In other words, the perfume component and the amine compound are first reacted to obtain the resulting amine reaction product as defined in the present invention, and only once it is formed, it is incorporated into the compositiof the invention . By being previously formed before incorporating it into the fully formulated composition, a better control of the compound being prepared is obtained. Therefore, interaction with the perfume composition that may be present in the fully formulated composition, and also any side reactithat may occur, is avoided. In addition, by means of such means of incorporation, an efficient control of the yield and purity of the compound is obtained. More preferably, when the composition of the invention comprises a perfume, the amine reaction product is incorporated into the composition separately from the perfume. By this, the amine reaction product and its subsequent release will be more controlled. Typically, the composition of the invention comprises ingredients that provide surfactant such as a fabric softening agent, or a surfactant such as those described below in the present invention as optional ingredients. When the compositicomprise a softening agent, the resulting composition is a softening composition.
Fabric softening agents A fabric softening component provides softness and antistatic properties to the treated fabrics. When used, the softening component will typically be present at a level sufficient to provide anti-aesthetic and softening properties. Said fabric softening component may be selected from a cationic, non-ionic, amphoteric or anionic fabric softening component.
Typical cationic softening components are the quaternary ammonium compounds or amine precursors thereof as defined below in the present invention.
A) Quaternary ammonium fabric softening active compound (1) The preferred quaternary ammonium fabric softening active compound has the formula:
or the formula:
where Q is a carbonyl unit that has the formula:
-o- each R unit is independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl and mixtures thereof, preferably methyl or hydroxyalkyl; each R1 unit is independently linear or branched C11-C22 alkyl, linear or branched Cn-C22 alkenyl and mixtures thereof;
R 2 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl and mixtures thereof; X is an anion that is compatible with active fabric softeners and auxiliary ingredients; the index m is from 1 to 4, preferably 2; the index n is from 1 to 4, preferably 2. An example of a fabric softening active that is preferred is a mixture of quaternized amines having the formula:
wherein R is preferably methyl; R1 is a linear or branched alkyl or alkenyl chain comprising at least 11 carbon atoms, preferably at least 15 atoms. In the above fabric softener example, the -O2CR1 unit represents a fatty acyl unit that is typically derived from a triglyceride source. The source of triglycerides is preferably derived from tallow, partially hydrogenated tallow, lard, partially hydrogenated butter, vegetable oils and / or partially hydrogenated vegetable oils, such as canola oil, safflower oil, peanut oil, sunflower oil, oil. corn, soybean oil, wood oil, rice bran oil and mixtures thereof. The fabric softening actives which are preferred in the present invention are the diester and / or quaternary ammonium diamide (DEQA) compounds, the diesters and diamides having the formula: wherein R, R1, X and n are the same as the defined hereinabove for formulas (1) and (2), and Q has the formula:
These preferred fabric softening actives are formed from the reaction of an amine with a fatty acyl unit to form an amine intermediate having the formula:
wherein R is preferably methyl, Q and R1 are as defined above in the present invention; followed by quaternization until the final softening active. Non-limiting examples of the preferred amines that are used to form the fabric softening actives of DEQA in accordance with the present invention include methyl-bis (2-hydroxyethyl) amine having the formula: methyl-bis (2-hydroxypropyl) amine which has the formula: methyl- (3-aminopropyl) (2-hydroxyethyl) amine having the formula: methyl-bis (2-aminoethyl) amine having the formula: triethanolamine having the formula: di (2-aminoethyl) ethanolamine which it has the formula: H2N H2 The counterion, XH above, can be any anion compatible with the softener, preferably the anion of a strong acid, for example, chloride, bromide, methylisulfate, etiisulfate, sulfate, nitrate and the like, more preferred chloride or metisulfate. The anion can also, but is less preferred, carry a double charge in which case X (_) represents half of a group. Sebum and canola oil are convenient and inexpensive sources of fatty acid acyl units which are suitable for use in the present invention as R units. The following examples are non-limiting examples of quaternary ammonium compounds suitable for use in the compositions of the present invention. The term "seboyl" as used later in the present invention indicates that unit R1 is obtained from a source of tallow triglycerides and is a mixture of alkyl or alkenyl units of fatty acid. Similarly, the use of the term canolyl refers to a mixture of alkyl or alkenyl units of fatty acid obtained from canola oil.
TABLE II Fabric softening active
N, N-di (tallowyloxyethyl) -N, N-dimethylammonium chloride; N, N-di (canolyl-oxy-ethyl) -N, N-dimethylammonium chloride; N, N-di (tallowyloxyethyl) -N-methyl, N- (2-hydroxyethyl) ammonium chloride; N, N-di (canolyl-oxy-ethyl) -N-methyl, N- (2-hydroxyethyl) ammonium chloride; N, N-di (2-tallowoyloxy-2-oxo-ethyl) -N, N-dimethylammonium chloride; N, N-di (2-canoli! Oxy-2-oxo-ethyl) -N, N-dimethylammonium chloride; N, N-di (2-tallowoxyethylcarbonylloxyeti) -N, N-dimethylammonium chloride; N, N-d- (2-canolylethylcarbonyloxyethyl) -N, N-dimethylammonium chloride; N- (2-tallowoyloxy-2-ethyl) -N- (2-seboxy-oxy-2-oxo-ethyl) -N, N-dimethylammonium chloride;
N- (2-Canyloxy-2-ethyl) -N- (2-canyloxy-2-oxo-ethyl) -N, N-dimethylammonium chloride;
N, N, N-tri (tallowyl-oxy-ethyl) -N-methylammonium chloride; N, N, N-trí (canaryl-oxy-ethyl) -N-methylammonium chloride; N- (2-tallowoyloxy-2-oxoethyl) -N- (tallowyl) -N, N-dimethylammonium chloride; N- (2-canolyloxy-2-oxoethyl) -N- (canolyl) -N, N-dimethylammonium chloride; Chloride of 1,2-diisoboxy-3-N, N, N-trimethylammoniopropane; and 1,2-dicanyloxy-3-N, N, N -trimethylammoniopropane Chloride; and mixtures of the above active ingredients.
Other examples of quaternary ammonium softening compounds are methyl bis (tallowamidoethyl) (2-hydroxyethyl) ammonium methylisulfate and methylbis methylisulfate (hydrogenated tallow amidoethyl) (2-hydroxyethyl) ammonium; these materials are available from Witco Chemical Company under the tradenames Varisoft® 222 and Varisoft® 110, respectively. N, N-di (tallowyloxyethyl) -N, N-dimethylammonium chloride in which the tallow chains are at least partially unsaturated is particularly preferred. The level of unsaturation contained within tallow, canola or other acyl fatty acid chain can be measured by the corresponding iodine (IV) value of the fatty acid, which in the present case should preferably be in the range of 5 to 100, distinguishing two categories of compounds that have an IV of less than or more than 25. In fact, for compounds that have the formula:
tallow fatty acid derivatives, when the Iodine Value is from 5 to 25, preferably 15 to 20, it has been found that a weight ratio of the cis / trans isomer of more than about 30/70, preferably more than about 50 / 50 and most preferably more than about 70/30, provides optimum concentration ability. For compounds of this type made from tallow fatty acids having an Iodine Value of more than 25, the ratio of cis to trans isomers has been found to be less critical, unless very high concentrations are required. Other suitable examples of fabric softening actives are derived from fatty acyl groups in which the terms "seboyl" and "canolyl" in the above examples are replaced by the terms "cocoyl, palmyl, lauryl, oleyl, ricinoleyl, stearyl, palmityl" , which correspond to the source of triglycerides from which the fatty acyl units are derived. These alternative fatty acyl sources can comprise unsaturated chains either completely saturated, or preferably at least partially saturated. As described hereinabove, the R units are preferably methyl, however, suitable fabric softening actives are described by replacing the term "methyl" in the above examples of Table I with the "ethyl, ethoxy, propyl, propoxy" units , isopropyl, butyl, isobutyl and t-butyl ". The counter on X in the examples of Table I can be suitably replaced by bromide, methylisulfate, formate, sulfate, nitrate and mixtures thereof. In fact, the X anion is present simply as a counter ion of the positively charged quaternary amino compounds. The scope of this invention is not considered limited to any particular anion. For the above ester fabric softening agents, the pH of the compositions herein is an important parameter of the present invention. In fact, it influences the stability of the quaternary ammonium compounds or amine precursors, especially in conditions of prolonged storage. The pH, as defined in the present context, is measured in the concentrated compositions at 20 ° C. Although these compositions can operate at a pH of less than about 6.0, for optimum hydrolytic stability of these compositions, the concentrated pH, measured under the conditions mentioned above, should preferably be in the range of about 2.0 to 5, preferably in the scale from 2.5 to 4.5, preferably around 2.5 to about 3.5. The pH of the compositions herein can be regulated by the addition of a Bronsted acid. Examples of suitable acids include inorganic mineral acids, carboxylic acids, in particular low molecular weight carboxylic acids (C 1 -C 5) and alkylsulfonic acids. Suitable inorganic acids include HCl, H2SO4, HNO3 and H3P4. Suitable organic acids include formic, acetic, citric, methylsulfonic and ethylsulphonic acids. The acids that are preferred are citric, hydrochloric, phosphoric, formic, methylsulphonic and benzoic acids. Mixtures of the active compounds of the formula (1) and (2) can also be prepared. 2) Other quaternary ammonium fabric softening compounds suitable for use herein are cationic nitrogen salts having two or more C8-C22 long chain aliphatic and acyclic hydrocarbon groups, or one such group and an arylalkyl group which they can be used alone or as part of a mixture are selected from the group consisting of: (i) non-cyclic quaternary ammonium salts having the formula:
wherein R is an acyclic and aliphatic C8-C22 hydrocarbon group, R is a saturated C1-C4 alkyl or hydroxyalkyl group, R8 is selected from the group consisting of groups R4 and R5, and A- is an anion such as defined above; (ii) diamino alkoxylated quaternary ammonium salts having the formula:
R 'A "
wherein n is equal to 1 to 5, and R1, R2, R5 and A "are as defined above, (iii) mixtures thereof Examples of the cationic nitrogen salts of the above class are the well-known salts of dialkyldimethylammonium such as ditallowdimethylammonium chloride, ditallowdimethylammonium methylisulfate, di (hydrogenated tallow) dimethylammonium chloride, distearyldimethylammonium chloride, dibenzyldimethylammonium chloride, Di (hardened tallow) dimelammonium chloride and ditallowdimethylammonium chloride are preferred. of commercially available diakyldimethylammonium salts useful in the present invention are di (hydrogenated tallow) dimethylammonium chloride (trade name Adogen® 442), ditallowdimethylammonium chloride (trade name Adogen®470, Praepagen® 3445), distearyldimethylammonium chloride (trade name Arosurf ® TA-100), all available from Witco Chemical Company Dibehenyldimethylammonium chloride is sold under the tradename Kemamine Q-280 2C by Humko Chemical Division of Witco Chemical Corporation. Dimethylstearylbenzylammonium chloride is sold under the trade names Varisoft® SDC by Witco Chemical Company and Ammonyx® 490 by Onyx Chemical Company.
B) Amine Fabric Softening Active Compound Amine fabric softening compounds suitable for use herein, which may be in the form of amine or cationic form, are selected from: i) reaction products of higher fatty acids with a polyamine selected from the group consisting of hydroxyalkylalkylenediamines and dialkylenetriamines and mixtures thereof. These reaction products are mixtures of several compounds in view of the multifunctional structure of the polyamines. The component i) that is preferred is a nitrogen compound selected from the group consisting of the reaction product mixtures or of some selected components of the mixtures. A preferred component i) is a compound selected from the group consisting of substituted imidazoline compounds having the formula:
wherein R7 is a hydrocarbon group of C5-C2? acyclic and aliphatic and R8 is an alkylene group of divalent C -? - C3. The materials of component i) are commercially available as: Mazamide® 6, sold by Mazer Chemicals or Ceranine® HC, sold by Sandoz Colors & Chemicals; stearic hydroxyethyl imidazoline sold under the tradenames of Alkazine® ST by Alkaril Chemicals Inc., or Schercozoline® S by Scher Chemicals, Inc .; N, N "-diseboalcoildiethylenetriamine; 1-tallowamidoethyl-2-seboimidazoline (wherein in the above structure R1 is an aliphatic C-? 5- C17 hydrocarbon group and R8 is a divalent ethylene group.) Some of the components i) also they can be dispersed first in a Bronsted acid dispersion auxiliary having a pKa value not greater than 4, as long as the pH of the final composition is not greater than 6. Some preferred dispersion aids are hydrochloric acid, Phosphoric acid or methylsulphonic acid Both N, N "-diseboalcoildiethylenetriamine and l-tallow (amidoethyl) -2-seboimidazoline are reaction products of tallow fatty acids and diethylenetriamine, and are precursors of the cationic fabric softening agent methylisulfate methyl-1 -seboamidoethyl-2-seboimidazolinium (see "Cationic Surface Active Agents as Fabrics Softeners", RR Egan, Journal of the American Oil Chemicals' Society, January 1978, pages 118-121). N, N "-diseboalcoildiethylene triamine and 1-tallowamidoethyl-2-seboimidazole can be obtained from the Witco Chemical Company as experimental chemical compounds. Methyl-1-tallowamidoethyl-2-seboimidazolinium methylisulfate is sold by Witco Chemical Company under the trade name Varisoft. ® 475. ii) softener that has the formula:
wherein each R 2 is an alkylene group of C 6, preferably an ethylene group; and G is an oxygen atom or a group -NR-; and each R, R1, R2 and R5 has the definitions given above and A "has the definitions given above for X".
An example of the compound i,) is 1-oleylamidoethyl-2-oleylimidazolinium chloride, wherein R 1 is an acyclic and aliphatic C 15 -C 7 hydrocarbon, R 2 is an ethylene group, G is an NH group, R 5 is a group methyl and A "is a chloride anion iii) softener having the formula:
wherein R, R1, R2 and A "are as defined above An example of compound iii) is the compound having the formula:
in which R1 is obtained from oleic acid. Additional fabric softening materials can be used in addition or as an alternative for the cationic fabric softener. These may be selected from nonionic, amphoteric or anionic fabric softening materials. The description of such materials can be found in documents US 4,327,133; US 4,421,792; US 4,426,299; US 4,460,485; US 3,644,203; US 4,661,269; US 4,439,335; US 3,861, 870; US 4,308,151; US 3,886,075; US 4,233,164; US 4,401, 578; US 3,974,076; US 4,237,016 and EP 472,178. Typically, said nonionic fabric softening materials have an HLB of about 2 to 9, very typically from 3 to 7. Such nonionic fabric softening materials tend to be easily dispersed either by themselves or when combined with other materials such as these. as the single and long alkyl chain cationic surfactant described in detail hereinafter. The dispersion capacity can be improved by using more single and long alkyl chain cationic surfactant, mixing with other materials as set forth hereinafter, use of warmer water and / or more agitation. In general, the selected materials should be relatively crystalline, higher melting (e.g.,> 40 ° C) and relatively insoluble in water. Preferred nonionic softeners are the partial fatty acid esters of polyhydric alcohols, or anhydrides thereof, wherein the alcohol, or anhydride, contains from 2 to 18, preferably from 2 to 8, carbon atoms, and each fatty acid portion contains from 12 to 30, preferably from 16 to 20 carbon atoms. Typically, such softeners contain from one to 3, preferably 2 fatty acid groups per molecule. The polyhydric alcohol moiety of the ester can be ethylene glycol, glycerol, poly (eg, di-, tri-, tetra-, penta-, and / or hexa-) glycerol, xylitol, sucrose, erythritol, pentaerythritol, sorbitol or sorbitan. Particularly preferred are sorbitan esters and polyglycerol monostearate. The fatty acid portion of the ester is usually derived from fatty acids having from 12 to 30, preferably from 16 to 20 carbon atoms, typical examples of said fatty acids being lauric acid, myristic acid, palmitic acid, stearic acid and behenic acid . The highly preferred optional nonionic softening agents for use in the present invention are the sorbitan esters, which are esterified dehydration products of sorbitol and the glycerol esters. The commercial sorbitan monostearate is a suitable material. Also useful are mixtures of sorbitan stearate and sorbitan palmitate having stearate / palmitate weight ratios ranging from about 10: 1 to about 1: 10, and the esters of
1, 5-sorbitan. Preferred herein are glycerol and polyglycerol esters, especially glycerol, diglycerol, triglycerol and polyglycerol mono- and / or diesters, preferably mono- (eg, polyglycerol monostearate with a trade name Radiasurf 7248). Useful glycerol and polyglycerol esters include monoesters with stearic, oleic, palmitic, lauric, isostearic, myristic and / or behenic acids, and the diesters of stearic, oleic, palmitic, lauric, isostearic, myristic and / or behenic acids. It is understood that the monoester contains a little di- and triester, etc. The "glycerol esters" also include the polyglycerol esters, eg, diglycerol to octaglycerol. The polyglycerol polyols are formed by condensing glycerin or epichlorohydrin with one another to link the glycerol moieties via ether linkages. The mono- and / or diesters of the polyglycerol polyols are preferred, typically the fatty acyl groups being those described hereinabove for the sorbitan and glycerol esters. The softening components of additional fabrics suitable for use in the present invention are the softening clays, such as those of low ion exchange capacity described in EP-A-0,150,531. Of course, the term "softening active" may also encompass mixed softening active agents. Among the classes of softening compounds that are preferred described above in the present invention are the fabric softening active compound of diester or quaternary ammonium diamide (DEQA). The fabric softening compounds of the present invention are present at levels from about 1%, up to 80% of the compositions of the present invention, depending on the embodiment of the composition which can be diluted with a preferred level of active ingredient from 5% up to 15%, or concentrated, with a preferred level of active ingredient from 15% to 50%, most preferred 15% up to 35% by weight of the composition. Fully formulated softening compositions preferably contain, in addition to the compounds described above in the present invention, one or more of the following ingredients.
(A) Polishes The compositions of the present invention may also optionally contain from 0.005% to 5% by weight of certain types of hydrophilic optical brighteners that also provide a dye transfer inhibiting action. If used, the compositions herein will preferably comprise from 0.001% to 1% by weight of said optical brighteners. The hydrophilic optical brighteners useful in the present invention are those having the structural formula:
wherein R-j is selected from anilino, N-2-bis-hydroxyethyl and NH-2-hydroxyethyl; R2 is selected from N-2-bis-hydroxyethyl, N-2-hydroxyethyl-N-methylamino, morphino, chloro and amino; and M is a salt-forming cation such as sodium or potassium.
When in the above formula, R-] is anilino, R2 is N-2-bis-hydroxyethyl and M is a cation such as sodium, the brightener is acid 4,4 ', bis [(4-anilino-6- (N -2-bis-hydroxyethyl) -s-triazin-2-yl) amino] -2,2'-styrene-disulfonic acid and disodium salt. This particular brightener species is sold under the trade name TinopaI-UNPA-G? R by Ciba-Geigy Corporation. Tinopal-UNPA-GX is the preferred hydrophilic optical brightener useful in the dryer-added compositions of the present invention. When in the above formula R1 is anilino, R2 is N-2-hydroxyethyl-N-2-methylamino and M is a cation such as sodium, the brightener is the disodium salt of acid 4,4, -bis [(4-anilino -6- (N-2-hydroxyethyl-N-methylamino) -s-triazin-2-yl) amino] -2,2, -stilbenedisulfonic acid. This particular kind of brightener is sold under the trademark Tinopal 5BM-GXR from Ciba-Geigy Corporation. When in the above formula R1 is anilino, R2 is morphino and M is a cation such as sodium, the brightener is the sodium salt of 4,4'-bis [(4-anilino-6-morphyl) -s-triazin -2-yl) amino] 2,2'-stilbenedisulfonic acid. This particular brightener species is sold commercially under the Tinopal AMS-GXR brand of Ciba-Geigy Corporation.
(B) Scattering Capability Aids Relatively concentrated compositions can be prepared containing quaternary ammonium diester compounds, both saturated and unsaturated, which are stable without the addition of concentration aids. However, the compositions of the present invention may require organic and / or inorganic concentration aids for? obtain even higher concentrations and / or to satisfy higher stability standards, depending on the other ingredients. These concentration aids which typically can be viscosity modifiers may be required, or preferred, to ensure stability under extreme conditions when particular levels of softening active are used. The surfactant concentration aids are typically selected from the group consisting of (1) individual long chain alkyl cationic surfactants; (2) nonionic surfactants; (3) amine oxides; (4) fatty acids and (5) mixtures thereof. These auxiliaries are described in WO 94/20597, specifically on page 14, line 12 to page 20, line 12, which is incorporated in the present invention for reference. When said dispersion capacity auxiliaries are present, the total level is from 2% to 25%, preferably from 3% to 17%, preferably from 4% to 15% and even more preferred from 5% to 13% by weight of the composition. These materials may be added as part of the raw material of the active softener, (I), for example, the individual long chain alkyl cationic surfactant and / or the fatty acid which are reactants used to form the biodegradable fabric softening active. as described above here, or are added as a separate component. The total dispersion capacity auxiliary level includes any quantity that may be present as part of the component (I).
(1) Cationic monoalkyl quaternary ammonium compound When the monoalkyl quaternary ammonium cationic compound is present, it typically does so at a level of 2% to 25%, preferably 3% to 17%, most preferred 4% to 15% , and even more preferred of
% to 13% by weight of the composition, the cationic monoalkyl quaternary ammonium compound being at least at an effective level. Said monoalkyl quaternary ammonium cationic compounds useful in the present invention are preferably the quaternary ammonium salts of the general formula: [R4N + (R5) 3] X "in which R4 is a C8-C22 alkyl or alkenyl group preferably alkyl or alkenyl group of C oC 8; most preferably an alkyl or alkenyl C10-C1 or Ci6-C 8;??? each R5 is an alkyl group of C - - C6 alkyl or substituted (for example, hydroxyalkyl), preferably an alkyl group of Cr C3, for example, methyl (more preferred), ethyl, propyl and the like, a benzyl group, hydrogen, a polyethoxylated chain with from 2 to 20 oxyethylene units, preferably from 2.5 up to 13 oxyethylene units, more preferred 3 to 10 oxyethylene units and mixtures thereof, and X "is as defined here above for formula (I). Especially preferred dispersion aids are monolauryltrimethylammonium chloride and monosebotrimethylammonium chloride, available from Witco under the tradenames Adogen®412 and Adogen® 471. monooleyl or monocanetrimethylammonium chloride available from Witco under the trade name Adogen® 417, monococotrimethylammonium chloride available from Witco under the tradename Adogen® 461 and monosoyatrimethylammonium chloride available from Witco under the tradename Adogen® 415. The R4 group may also be attached to the cationic nitrogen atom by means of a group containing one, or more, ester, amide, ether, amine, etc., linking groups, which may be desirable for an increased concentration capacity of component (I), etc. Said linking groups are preferably within one to three carbon atoms of the nitrogen atom. The monoalkyl quaternary ammonium cationic compounds also include the C8-C22 alkylcholine esters. Preferred dispersion aids of this type have the formula: R1C (O) -O-CH2CH2N + (R) 3X "in which R1, R and X "are as previously defined. The dispersibility aids include highly preferred ester of C 2 cococolínico Cu and sebocolínico ester C- |? 6-C 8?. Suitable long chain biodegradable single chain alkyl dispersion auxiliaries containing an ester linkage in the long chains are described in the U.S.A. No. 4,840,738, said patent incorporated for reference.
When the dispersibility aid comprises alquilcolínicos esters, preferably the compositions also contain a small amount, preferably from 2% to 5% by weight of the composition, of organic acid. Organic acids are described in European Patent Application No. 404,471, which is incorporated in the present invention for reference. Preferably, the organic acid is selected from the group consisting of glycolic acid, acetic acid, citric acid and mixtures thereof. The ethoxylated quaternary ammonium compounds which can serve as the dispersion aids auxiliary include ethylbis (ethoxyethanol) alkylammonium ethiisulfate with 17 moles of ethylene oxide, available under the tradename Variquat®66 from Witco Corporation; polyethylene glycol (15) oleammonium chloride, available under the tradename Ethoquad® 0/25 from Akzo, and polyethylene glycol (15) cocoamonium chloride, available under the tradename Ethoquad® C / 25 from Akzo. Quaternary compounds having only a single long alkyl chain can protect the cationic softener from interacting with anionic surfactants and / or detergent builders that are carried to the rinse from the wash solution.
(2) Nonionic Surfactant (Alkoxylated Materials) Suitable nonionic to serve as the viscosity modifier / dispersibility surfactants include addition products of ethylene oxide and, optionally, propylene oxide, with fatty alcohols, fatty acids, fatty amines, etc. They are mentioned in the present invention as ethoxylated fatty alcohols, ethoxylated fatty acids and ethoxylated fatty amines. Any of the alkoxylated materials of the particular type described in the present invention can be used as the nonionic surfactant. In general terms, the nonionic surfactants of the present invention, when used alone in liquid compositions, are at a level of from 0% to 5%, preferably from 0.1% to 5%, more preferably from 0.2% to 3%. %. Suitable compounds are substantially water-soluble surfactants of the general formula: R2-Y- (C2H4O) z-C2H4OH in which R2 for both liquid and solid compositions is selected from the group consisting of alkyl- and / or acyl- primary, secondary and branched chain hydrocarbons; primary, secondary and branched alkenylhydrocarbyl groups; and primary and secondary branched-chain alkyl- and alkenyl-substituted phenolic hydrocarbyl groups; said hydrocarbyl groups have a hydrocarbyl chain length of 8 to 20, preferably 10 to 18 carbon atoms. Most preferably, the hydrocarbyl chain length for liquid compositions is from 16 to 18 carbon atoms, and for solid compositions it is from 10 to 14 carbon atoms. In the general formula for the ethoxylated nonionic surfactants of the present invention, Y is typically -O-, -C (0) O-, -C (0) N (R) -, or -C (0) N ( R) R-, preferably -O-, and in which R2, and R, when present, have the meanings given above in the present invention, and / or R can be hydrogen, and z is at least 8, preference at least 10-11. The yield and, normally, the stability of the softening composition decrease when less ethoxylate groups are present. The nonionic surfactants of the present invention are characterized by a HLB (hydrophilic-lipophilic balance) of 7 to 20, preferably from 8 to 15. Of course, by defining R2 and the number of ethoxylate groups, the HLB of the surfactant is, in general, determined. However, it should be noted that the ethoxylated nonionic surfactants useful in the present invention, for concentrated liquid compositions, contain relatively long chain R2 groups and are relatively highly ethoxylated. Although shorter alkyl chain surfactants having short ethoxylated groups may possess the necessary HLB, they are not as effective in the present invention. For compositions with higher levels of perfume, nonionic surfactants such as viscosity modifiers / dispersing ability over the other modifiers described in the present invention are preferred. Examples of nonionic surfactants follow. The nonionic surfactants of this invention are not limited to these examples. In the examples, the integer defines the number of ethoxy groups (EO) in the molecule.
(3) Amine oxides Suitable amine oxides include those with an alkyl or hydroxyalkyl portion of 8 to 22 carbon atoms, preferably 10 to 18 carbon atoms, more preferred of 8 to 14 carbon atoms, and two portions alkyl selected from the group consisting of alkyl groups and hydroxyalkyl groups with 1 to 3 carbon atoms. Examples include dimethyloctylamine oxide, diethyldecylamine oxide, bis- (2-hydroxyethyl) dodecylamine oxide, dimethyldodecylamine oxide, dipropyltetradecylamine oxide, methylethylhexadecylamine oxide, dimethyl-2-hydroxyoctadecylamine oxide, and coconut fatty acid alkyldimethylamine oxide. .
(C) Stabilizers Stabilizers may be present in the compositions of the present invention. The term "stabilizer", as used in the present invention, includes antioxidants and reducing agents. These agents are present at a level of from 0% to 2%, preferably from 0.01% to 0.2%, more preferred from 0.035% to 0.1% for antioxidants, and most preferably from 0.01% to 0.2% for reducing agents. These ensure adequate odor stability under long-term storage conditions. Antioxidant and reducing agent stabilizers are especially critical for unscented or low-aroma products (with or without low perfume). Examples of antioxidants that can be added to the compositions of this invention include a mixture of ascorbic acid, ascorbic palmitate and propylgalate, available from Eastman Chemical Products, Inc., under the trade names Tenox® PG and Tenox® S-1; a mixture of BHT (butylated hydroxytoluene), BHA (butylated hydroxyanisole), propylgalate and citric acid, available from Eastman Chemical Products, Inc., under the trade name Tenox®-6; butylated hydroxytoluene, available from UOP Process Division under the trade name Sustane® BTH; tertiary butylhydroquinone, Eastman Chemical Products, Inc., as Tenox® TBHQ; natural tocopherols, Eastman Chemical Products, Inc., as Tenox® GT-1 / GT-2; and butylated hydroxyanisole, Eastman Chemical Products, Inc., as BHA; long chain esters (C8-C22) of gallic acid, for example, dodecylgalate; Irganox® 1010; Irganox® 1030; Irganox® B 1171; Irganox® 1425; Irganox® 3114; Irganox® 3125 and mixtures thereof; preferably Irganox® 3125; Irganox® 1425, Irganox® 3114 and mixtures thereof; most preferred Irganox® 3125 alone or mixed with citric acid and / or other chelating agents such as isopropyl citrate, Dequest® 2010, available from Monsanto with a chemical name of 1-hydroxyethylidene-1,1-diphosphonic acid (etridronic acid) and Tiran ®, available from Kodak with a chemical name of 4,5-dihydroxy-m-benzenesulfonic acid / sodium salt and DTPA®, available from Aldrich with a chemical name of diethylenetriaminepentaacetic acid.
(D) Soil releasing agent In the present invention, an optional soil release agent can be added. Typical levels of incorporation into the composition are from 0% to 10%, preferably from 0.2% to 5% of a soil release agent. Preferably, said soil release agent is a polymer. The soil release agents are conveniently used in fabric softening compositions of the present invention. Any polymeric soil release agent known to the person skilled in the art can be optionally employed in the compositions of this invention. Polymeric soil release agents are characterized by having both hydrophilic segments, to render the surface of hydrophobic fibers such as polyester and nylon hydrophobic, as hydrophobic segments to deposit on the hydrophobic fibers and remain adhered to them until the washing and rinsing cycles are completed, thus serving as an anchor for the hydrophilic segments. This can make stains that appear after treatment with the soil release agent easier to clean in subsequent cleaning procedures. If they are used, the soil release agents will generally comprise from about 0.01% to about 10.0% by weight of the detergent compositions of the present invention, typically from about 0.1% to 5%, preferably from about 0.2% to about 3.0%. The following publications, all included for reference, disclose soil release polymers for use in the present invention. The patent of E.U.A. No. 3,959,230 of Hays, issued May 25, 1976; the patent of E.U.A. No. 3,893,929 of Basadur, issued July 8, 1975; the patent of E.U.A. No. 4,000,093 of Nicol et al., Issued December 28, 1976; the patent of E.U.A. No. 4,702,857 to Gosselink, issued October 27, 1987; the patent of E.U.A. No. 4,968,451, by Scheibel et al., Issued November 6; the patent of E.U.A. No. 4,702,857 to Gosselink, issued October 27, 1987; the patent of E.U.A. No. 4,711, 730 of Gosselink et al., Issued December 8, 1987; the patent of E.U.A. No. 4,721,580 to Gosselink, issued January 26, 1988; the patent of E.U.A. No. 4,877,896 of Maldonado et al., Issued on October 31, 1989; patent of E.U.A. No. 4,956,447 to Gosselink et al., Issued September 11, 1990; the patent of E.U.A. No. 5,415,807 to Gosselink et al., Issued May 16, 1995; European Patent Application 0 219 048, published on April 22, 1987 by Kud et al. Additional suitable soil release agents are described in the US patent. No. 4,201, 824 of Violland et al .; the patent of E.U.A. No. 4,240,918 to Lagasse et al .; the patent of E.U.A. No. 4,525,524 to Tung et al .; the patent of E.U.A. No. 4,579,681 to Ruppert et al .; patent of E.U.A. No. 4,240,918; patent of E.U.A. No. 4,787,989; patent of E.U.A. No. 4,525,524; EP 279,134 A, 1988, for Rhone-Poulenc Chemie; EP 457,205 A for BASF (1991); and DE 2,335,044 for Unilever N.V., 1974, all incorporated in the present invention for reference. Commercially available soil release agents include METOLOSE SM100, METOLOSE SM200, manufactured by Shin-etsu-Kagaku Kogyo KK, SOKOLAN material, for example SOKOLAN HP-22, available from BASF (Germany), ZELCON 5126 (from Dupont) and MILEASE T (from ICI).
(E) Cream Dispersant In the present invention, the premix can be combined with an optional cream dispersant, different from the soil release agent, and can be heated to the temperature of the melting points of the components, or higher. Preferred cream dispersants in the present invention are formed by highly ethoxylated hydrophobic materials. The hydrophobic material may be a fatty alcohol, fatty acid, fatty amine, fatty acid amide, amine oxide, quaternary ammonium compound, or the hydrophobic portions used to form soil release polymers. Preferred cream dispersants are highly ethoxylated, for example, with more than 17, preferably more than 25, preferably more than 40 moles of ethylene oxide per molecule, on average; the polyethylene oxide portion being from 76% to 97%, preferably from 81% to 94% of the total molecular weight. The level of the cream dispersant is sufficient to maintain the cream at an acceptable, preferably imperceptible, level for the consumer under the conditions of use, but not enough to adversely affect the softening. For some purposes, it is convenient that cream does not exist. Depending on the amount of anionic or non-ionic detergent, etc., used in the wash cycle of a typical laundry process, the efficiency of the rinse steps before the introduction of the compositions of the present invention, and the hardness of water, the amount of anionic or nonionic detergent surfactant and builder (especially phosphates and zeolites) trapped in the (laundry) fabric will vary. Normally, the minimum amount of the cream dispersant should be used to avoid adversely affecting the softening properties. Typically, the cream dispersion requires at least 2%, preferably at least 4% (at least 6% and preferably at least 10% for maximum cream removal) based on the level of active softening agent. However, at levels of 10% (with respect to the softening material) or more, there is a risk of losing softening efficacy of the product, especially when the fabrics contain high proportions of nonionic surfactant that has been absorbed during the washing operation. . Preferred cream dispersants are: Brij 700R; Varonic U-250R; Genapol T-500R, Genapol T-800R, Plurafac A-79R and Neodol 25-50R.
(F) Bactericides Examples of bactericides used in the compositions of this invention include glutaraldehyde, formaldehyde, 2-bromo-2-nitro-propane-1,3-diol, sold by Inolex Chemicals, located in Philadelphia, Pennsylvania under the trade name Bronopol®, and a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one, sold by Rohm and Haas Company under the trade name of Kathon, to 1, 000 ppm by weight of the agent.
(G) Perfume The present invention may contain any perfume compatible with fabric softener. Suitable perfumes are described in the U.S.A. No. 5,500,138, incorporated in the present invention for reference. As used herein, "perfume" includes a substance or mixture of fragrant substances that include natural fragrances (ie, obtained by extracting flowers, herbs, leaves, roots, barks, wood, buds or plants), artificial (ie, a mixture of oils or different natural oil constituents) and synthetic (ie synthetically produced). Such materials are often accompanied by auxiliary materials such as fixatives, extenders, stabilizers and solvents. These auxiliaries are also included within the meaning of "perfume" as used herein. Typically, perfumes are complex mixtures of a plurality of organic compounds. Examples of perfume ingredients useful in the perfumes of the compositions of the present invention include, without limitation, hexyl cinnamic aldehyde, amyl cinnamic aldehyde, amyl salicylate, hexyl salicylate, terpineol, 3,7-dimethyl-s-2,6-octadien-1-ol, 2,6-dimethyl-2-octanol, 2,6-dimethyl-7-octen-2-ol , 3,7-dimethyl-3-octanol, 3,7-dimethyl-trans-2,6-octadien-1-ol, 3,7-dimethyl-6-octen-1-ol, 3,7-dimethyl-1 -octanol, 2-methyl-3- (para-tert-butylphenyl) propionaldehyde, 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene-1-carboxaldehyde, tricyclodecenyl propionate, tricyclodecenyl acetate, anisaldehyde, 2- methyl-2- (para-iso-propylphenyl) propionaldehyde, ethyl 3-methyl-3-phenylglycidate, 4- (para-hydroxyphenyl) butan-2-one, 1- (2,6,6-trimethyl-2-cyclohexen -1-yl) -2-buten-1 -one, para-methoxyacetophenone, para-methoxy-alpha-phenylpropene, methyl 2-n-hexyl-3-oxo-cyclopentanecarboxylate, gamma-undecalactone. Additional examples of fragrance materials include, without limitation, orange oil, lemon oil, grapefruit oil, bergamot oil, clove oil, gamma-dodecalactone, 2- (2-pentyl-3-oxo-cyclopentyl) acetate. methyl, beta-naphthyl methyl ether, methyl-beta-naphthyl ketone, coumarin, decyl aldehyde, benzaldehyde, 4-tert-butylcyclohexyl acetate, alpha.alpha-dimethylphenethyl acetate, methylphenylcarbinyl acetate, Schiff's base of 4- (4- hydroxy-4-methylpentyl) -3-cyclohexene-1-carboxaldehyde and methyl anthranilate, cyclic diester of ethylene glycol tridecanedioic acid, 3,7-dimethyl-2,6-octadiene-1-nitrile, gamma-methyl-ionone, alpha ionone, beta-ionone, Citrus aurantium oil, metilcedrilone, 7-acetyl-1, 2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethylnaphthalene, methylionone, methyl-1 , 6,10-trimethyl-2,5,9-cyclododecatrien-1-yl-ketone; 7-acetyl-1,1, 3,4,4,6-hexamethyltetralin; 4-acetyl-6-tert-butyl-1,1-dimethylindane; benzophenone; 6-acetyl-1,1, 2,3,3,5-hexamethylindane, 5-acetyl-3-isopropyl-1,1,6-tetramethylindane; 1-dodecanal; 7-hydroxy-3,7-dimethyloctanal; 10-undequen-1-al; iso-hexenylcyclohexylcarboxaldehyde, formyltriciclodecane; cyclopentadecanolide; 16-hydroxy-9-hexadequenoic acid lactone; 1, 3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-gamma-2-benzopyran; ambroxane; dodecahydro-3a, 6,6,9a-tetramethylnaphtho- [2,1-b] furan; cedar!; 5- (2,2,3-trimethyl-cyl-Iopent-3-enyl) -3-methylpentan-2-ol; 2-ethyl-4- (2,2,3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol; caryophyllene alcohol; Cedaryl acetate; para-tert-butyclohexyl acetate; patchouli; olibanum resinoid; labadand; vetiver; balsam of copaiba; fir balsam; and condensation products of: hydroxytronelalum and methyl anthranilate; hydroxy-citronellal ether; phenylacetaldehyde e ndol; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexen-1 -carboxaldehyde and methyl anthranilate. More examples of perfume components are: geraniol, geranyl acetate; linalool; linalyl acetate; tetrahydrolinalool; citronellol; citronellyl acetate; dihydromyrcenol; Dihydromyrcenyl acetate; tetrahydromyrcenol; terpinyl acetate; nopol; nopyl acetate; 2-phenylethanol; 2-phenylethyl acetate; benzyl alcohol; benzyl acetate; benzyl salicylate; Benzyl benzoate; styrallylacetate; dimethylbenzyl carbinol; Methylphenylcarbinyl trichloromethylphenylcarbinyl acetate; isononyl acetate;
vetiveril acetate; vetlverol; 2-methyl-3- (p-tert-butylphenyl) -propanal; 2-methyl-3- (p-isopropylphenyl) -propanal; 3- (p-tert-butylphenyl) -propanal; 4- (4-methyl-3-pentenyl) -3-cyclohexenecarbaldehyde; 4-acetoxy-3-pentyl-tetrahydro-pyran; methyl dihydrojasmonate; 2-n-heptylcyclopentanone; 3-methyl-2-pentyl-cyclopentanone; n-decanal; n-dodecanal; 9-decenol-1; phenoxyethyl isobutyrate; dimethylacetalphenylacetaldehyde; diethylacetalphenylacetaldehyde; geranonitrile; citronelonitrile; acetalcedril; 3 -socanfilcyclohexanol; cedril methylether; isolongifolanone; aubepin nitrile; aubepin; heliotropin; eugenol; vanillin; diphenyl oxide; hydroxy citronone ionones; methylionones; isomethylionones; Frogs; cis-3-hexenol and esters thereof; Inzan musk fragrances, tetralin musk fragrances, isocroman musk fragrances, macrocyclic ketones, musk fragrances of macrolactone, ethylene brasilate. The perfumes useful in the compositions of the present invention are substantially free of halogenated materials and nitro-alkyls. Suitable solvents, diluents or vehicles for the aforementioned perfume ingredients are, for example, ethanol, isopropanol, diethylene glycol, monoethyl ether, dipropylene glycol, diethyl phthalate, triethyl citrate, etc. The amount of said solvents, diluents or vehicles incorporated in the perfumes is preferably kept to the minimum necessary to produce a homogeneous perfume solution. The perfume may be present at a level of from 0% to 10%, preferably from 0.1% to 5%, more preferred from 0.2% to 3% by weight of the finished composition. The fabric softening compositions of the present invention provide improved deposition of perfume on the fabrics.
(H) Chelating agents The compositions and methods of the present invention may optionally employ one or more copper and / or nickel chelating agents ("chelators"). Said water-soluble chelating agents can be selected from the group consisting of aminocarboxylates, aminophosphonates, polyfunctionally substituted aromatic chelating agents and mixtures thereof, as defined hereinafter. The whiteness and / or brightness of the fabrics is substantially improved or restored by said chelating agents, and improve the stability of the materials in the compositions. Without intending to be limited by theory, it is believed that the benefit of these materials is due in part to their exceptional ability to remove iron and manganese solutions from the washing solutions through the formation of soluble chelates. Aminocarboxylates useful as optional chelating agents include ethylenediaminetetraacetates, N-hydroxyethylenediaminetriacetates, nitrile-triacetates, ethylenediaminetetrapropionates, triethylenetetraminehexaacetates, diethylenetriaminpentaacetates and ethanololdiglicines, alkali metal, ammonium and substituted ammonium salts thereof and mixtures thereof.
The aminophosphates are also suitable for use as chelating agents in the compositions of the invention when at least low levels of total phosphorus are allowed in the detergent compositions and include ethylenediaminetetrakis (methylenephosphonates) as DEQUEST. Preferably, these aminophosphonates do not contain alkyl or alkenyl groups with more than about 6 carbon atoms. Polyfunctionally substituted aromatic chelating agents are also useful in the compositions of the present invention.
See U.S. Pat. No. 3,812,044 issued May 21, 1974 to Connor et al. Preferred compounds of this type in acid form are dihydroxydisulfobenzenes such as 1,2-dihydroxy-3,5-disulfobenzene. A preferred biodegradable chelator for use in the present invention is ethylenediamine disuccinate ("EDDS"), especially the [S, S,] isomer as described in the U.S. Patent. No. 4,704,223 issued November 3, 1987 to Hartman and Perkins. The compositions of the present invention may also contain water-soluble salts of methyl glycine-di-acetic acid (MGDA) (or the acid form) as a chelator or associated detergency builder., useful for example with insoluble improvers such as zeolites, layered silicates and the like. Preferred chelating agents include DETMP, DETPA, NTA, EDDS and mixtures thereof. If used, these chelating agents should generally comprise from about 0.1% to about 15% by weight of the fabric care compositions of the present invention. More preferred, if used, chelating agents should comprise from about 0.1% to 3.0% by weight of said compositions.
(I) Crystal growth inhibitor The compositions of the present invention may also contain a crystal growth inhibiting component, preferably an organodisphosphonic acid component, preferably incorporated at a level of 0.01% up to 5%, more preferably 0.1% up to 2% by weight of the compositions. By "organodiphosphonic acid" is meant in the present invention an organodiphosphonic acid which does not contain nitrogen as part of its chemical structure. This definition therefore excludes organo-aminophosphonates, which however can be included in the compositions of the invention as heavy metal ion sequestering components. The organodiphosphonic acid is preferably a diphosphonic acid of C -? - C4, more preferred is a diphosphonic acid of C2, such as ethylene diphosphonic acid, or more preferred still ethane-1-hydroxy-1,1-diphosphonic acid
(HEDP) and may be present in partially or completely ionized form, particularly as a salt or complex. Even useful as a crystal growth inhibitor in the present invention are organic monophosphonic acids. The organomonophosphonic acid or one of its salts or complexes are also suitable for use as a CGI. Organomonophosphonic acid refers in the present invention to an organomonophosphonic acid that does not contain nitrogen as part of its chemical structure. As a consequence, this definition excludes organo-aminophosphonates, which, however, can be included in compositions of the invention as heavy metal ion sequestrants. The organomonophosphonic acid component can be present in its acid form or in the form of one of its salts or complexes with a suitable counter cation. Preferably, any of the salts / complexes is soluble in water, the salts / complexes of alkali metal and alkaline earth metal being especially preferred. A preferred organomonophosphonic acid is 2-phosphonobutane-1, 2,4-tricarboxylic acid commercially available from Bayer under the trade name of Bayhibit.
(J) Enzymes The compositions and methods herein may optionally employ one or more enzymes such as lipases, proteases, cellulase, amylases and peroxidases. An enzyme that is preferred to be used in the present invention is a cellulase enzyme. In fact, this type of enzyme will also provide a benefit of color care to the treated fabric. Cellulases useful herein include both bacterial and fungal cellulases, which preferably have an optimum pH between 5 and 9.5. The patent of E.U.A. 4,435,307 describes suitable fungal cellulases from Humicola nsolens or from Humicola strain DSM1800 or a cellulase-producing fungus 212 belonging to the genus Aeromonas, and cellulase extracted from the hepatopancreas of a marine mollusk Dolabella Auricular Solander. The cellulases. suitable also described in GB-A-2,075,028; GB-A-2,095,275 and DE-OS-2,247,832. CAREZYME® and CELLUZYME® (Novo) are especially useful. Other suitable cellulases are also described in WO 91/17243 to Novo, WO 96/34092, WO 96/34945 and EP-A-0,739,982. In practical terms for current commercial preparations, typical amounts are 5 mg by weight, most preferably 0.01 mg to 3 mg, of active enzyme per gram of the detergent composition. In other words, the compositions of the present invention will typically comprise from 0.001% to 5%, preferably from 0.01% to 1% by weight of a commercial enzyme preparation. In particular cases in which the activity of the enzyme preparation can be defined in another way such as with cellulases, the corresponding activity units are preferred (eg, CEVU or Cellulase Equivalent Viscosity Units). For example, the compositions of the present invention may contain cellulase enzyme at a level equivalent to an activity of 0.5 to 1000 CEVU / gram of composition. The cellulase enzyme preparations which are used for the purpose of formulating the compositions of this invention typically have an activity between 1,000 and 10,000 CEVU / gram in liquid form, and about 1, 000 CEVU / gram in solid form.
(K) Liguid Vehicle Another optional, but preferred, ingredient is a liquid vehicle. The liquid vehicle used in the present compositions is preferably at least mostly water due to its low cost, relative availability, safety and compatibility with the environment. The water level in the liquid vehicle is preferably at least 50%, more preferred at least 60%, by weight of the vehicle. Mixtures of water and low molecular weight organic solvent are useful, for example < 200, for example lower alcohols such as ethanol, propanol, isopropanol or butanol. Low molecular weight alcohols include monohydric, dihydric (glycol, etc.), trihydric (glycerol, etc.) alcohols and polyhydric higher alcohols (polyols).
(L) Other optional ingredients The present invention may include optional components used in a conventional manner in compositions for treating textile materials, for example: colorants; conservatives; surfactants; anti-shrinkage agents; agents for the tightening of fabrics; localized application agents; germicides; fungicides; antioxidants such as butylated hydroxytoluene, anti-corrosion agents, 1O3 enzyme stabilizers, materials effective to inhibit transfer and dyes from one fabric to the other during the cleaning process (i.e., transfer inhibiting agents), hydrotropes, processing aids, dyes or pigments and the like. The present invention may also include other compatible ingredients, including those described in WO 96/02625, WO 96/21714 and WO 96/21715.
FORM OF COMPOSITION The composition of the invention can take a variety of physical forms including liquid, gel, foam in aqueous or non-aqueous form, granular and tablet form. When in liquid form, the composition can also be dispensed using dispensing means such as a spray dispenser or an aerosol dispenser.
Spray Dispenser The present invention also relates to said compositions incorporated in a spray dispenser to create an article of manufacture that can facilitate the treatment of textile articles and / or surfaces with said compositions containing the reaction product of amine and other ingredients (Examples are cyclodextrins, polsaccharides, polymers, surfactants, perfume, softener), at a level that is effective but not perceptible when it dries on surfaces. The spray dispenser comprises manually activated and manually operated spray media, and a container containing the treatment composition. In the publication WO 96/04940, page 19, row 21 to page 22 row 27, a typical description of said spray dispenser can be found. Preferably, the articles of manufacture are accompanied by the instructions for use to ensure that the consumer applies sufficient ingredient of the composition to produce the desired benefit. Typical compositions to be dispensed from a sprayer contain a level of amine reaction product from about 0.01% to about 5%, preferably from about 0.05% to about 2%, more preferably from about 0.1% to about 1% by weight of the composition of use.
Method of use Also provided in the present invention is a method for providing a delayed release of an active ketone or aldehyde, comprising the step of contacting the surface to be treated with a compound or composition of the invention, and then subjecting the surface treated with a material, preferably an aqueous medium such as moisture or any other means capable of releasing the active compound from the amine reaction product. By "surface" is meant any surface on which the compound can be deposited. Typical examples of such materials are fabricshard surfaces such as tableware, floors, bathrooms, toilets, kitchens, skin and other surfaces that require a delayed release of an active ketone or aldehyde, such as stretcher objects such as stretchers for animals. Preferably, the surface is a fabric. By "delayed release" is meant release of the active component (e.g. perfume) for a longer period than with the use of the active component (e.g. perfume) alone.
Abbreviations used in the following examples of compositions of the invention In the examples of compositions, the identifications of the abbreviated components have the following meanings:
DEQA: Di- (tallowyloxyethyl) dimethylammonium chloride DTDMAC: Disodbodimethylammonium chloride DEQA (2): Di- (tallow soft-oyloxy-ethyl) hydroxyethylmethyl ammonium chloride DTDMAMS: Disodbodimethylammonium methysulfate SDASA: Ratio 1: 2 of stearyldimethylamine: triple-pressed stearic acid. Fatty acid: stearic acid of IV = 0 Electrolyte: Calcium chloride PEG Polyethylene glycol 4,000 Neodol 45-13: C14-C15 linear primary alcohol ethoxylate, sold by Shell Chemical Co. Cellulase: Cellulite enzyme sold under the trade name Carezyme, Celluzyme and / o Endolase by NOVO Nordisk A / S Silicone antifoam: Polydimethylsiloxane foam controller with siloxane-oxyalkylene copolymer as dispersion agent with a ratio of said controller to said dispersing agent from 10: 1 to 100: 1 PEI: Polyethyleneimine with an average molecular weight of 1800 and an average degree of ethoxylation of 7 ethyleneoxy residues per nitrogen HEDP: 1, 1-Hydroxyethanediphosphonic acid ARP1: Reaction product of ethyl 4-aminobenzoate amine with 2,4-dimethyl-3-cyclohexen -1-carboxaldehyde, prepared as in the synthesis example I ARP2: Reaction product of aminobenzoic acid amine with 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde, pr Prepared as in synthesis example I ARP3: Amine reaction product of Lupasol P with a-damascone, prepared as in synthesis example III
ARP4: Reaction product of D-glucamine amine with 1 7 7 citronellal, prepared as in synthesis example II
ARP5: Amine reaction product of Lupasol HF with a-damascone, prepared as in synthesis example III
Polymer: Polyvinylpyrrolidone K90 available from BASF under the trade name Luviskol K90 Dye fixation: Dye fixation commercially available from Clariant under the tradename Cartafix CB Polyamine: 1,4-Bis- (3-aminopropyl) piperazine Bayhibit AM: Acid 2- phosphonobutane-1, 2,4-tricarboxylic acid commercially available from Bayer Fabric softening active: Di- (canoloyl-oxy-ethyl) hydroxyethylmethyl ammonium methylisulfate HPBDC: Hydroxypropyl beta-cyclodextrin RAMEB: randomly methylated beta-cyclodextrin Bardac 2050: Chloride dioctyldimethylammonium, 50% solution Bardac 22250: Didecyldimethylammonium chloride, 50% solution Genamin C100: Coconut fat amine ethoxylated with 10 moles of ethylene oxide and commercially available from Clariant Genapol V4463: Coconut alcohol ethoxylated with 10 moles of ethylene oxide and commercially available from Clariant Silwet 7604: Polyalkyleneoxide polysiloxanes of MW 4000 of formula R- (CH 3) 2 SiO - [(CH 3) 2 SiO] a- [(CH3) (R) SiO] bSi (CH3) 2-R, where the sum of a + b is 21, and commercially available from Osi Specialties, Inc., Danbury, Connecticut Silwet 7600: PM polyalkylenoxide polysiloxanes 4000 of formula R- (CH3) 2SiO - [(CH3) 2SiO] a - [(CH3) (R) SiO] b-Si (CH3) 2-R, where the sum of a + b is 11, and commercially available from Osi Specialties, Inc., Danbury, Connecticut
The following are examples of synthesis of the compounds defined in the present invention.
I. Synthesis of ethyl 4-aminobenzoate with 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde
To a stirred and ice-cooled solution of 10 g of 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde (0.07 mol) in 35 ml of EtOH and molecular sieves (4?, 20 g), 1 eq. . of the amine by means of an addition funnel. The reaction mixture was stirred under a nitrogen atmosphere and protected from light. After 6 days, the mixture was filtered and the solvent was removed. The yield of imine formation was approximately 90%. Similar results were obtained when 2,4-dimethyl-3-cyclohexen-1 -carboxaldehyde was replaced with bourgeonal, or trans-2-nonenal. Additionally, similar results were obtained when ethyl 4-aminobenzoate was replaced with 4-aminobenzoic acid.
II. Synthesis of D-glucamine with 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde
To an ice-cooled solution of 1 mmol of D-glucamine in about 30 mL of EtOH and molecular sieves (4 A, 5 g), 1 eq. of 2,4-dimethyl-3-cyclohexen-1 -carboxaldehyde. The reaction was stirred under a nitrogen atmosphere and protected from light. After 3 to 4 days, the molecular sieves and the solvent were removed by filtration and evaporation, respectively. The solid mine was obtained in 85 to 90% yield. Similar results were obtained when 2,4-dimethyl-3-cyclohexen-1-carboxaldehyde was replaced with citronellal, trans-2-nonenal or decanal.
Ill Synthesis of Lupasol with Damascona
The ß-amino ketone was prepared from Lupasol G100 (commercially available from BASF, contained 50% water, 50% Lupasol G100, MW 5000) and a-damascone, using any of these three different procedures described below: 1. Dried Lupasol G100 commercially available, using the following procedure: 20 g of the Lupasol solution was dried on the rotary evaporator for several hours. The residue obtained, still containing 4.5 g of H 2 O, was azeotropically distilled in the rotary evaporator using toluene. The residue was then placed in the desiccator and dried at 60 ° C (using P205 as water absorbing material). Based on the weight obtained, the authors concluded that the oil contained less than 10%
H2O. Based on the NMR spectrum they concluded that this is probably less than 5%. This dry mixture was then used in the preparation of β-amino ketones. 1.38 g of the dried Lupasol G100 was dissolved in 7 ml of ethanol. The solution was stirred gently with a magnetic stirrer for a few minutes before adding 2 g of Na2SO (anhydrous). After stirring again for a few minutes, 2.21 g of a-damascone was added over a period of 1 minute. After two days of reaction, the mixture was filtered on a Celite filter (see above), and the residue was washed thoroughly with ethanol. Approximately 180 ml of a clear foaming filtrate were obtained. This was concentrated to dryness using a rotary evaporator, and dried over P2Os in a desiccator at room temperature. Approximately 3.5 of a colorless oil was obtained. 2. 4.3 g of Lupasol G100 (without drying) was dissolved in 10 ml of ethanol. The solution was stirred with a magnetic stirrer for a few minutes before adding 3.47 g of a-damascone over a period of 1.5 minutes. After 2 days of reaction at room temperature, the reaction mixture was filtered over Celite (see above) and the residue was washed thoroughly with ethanol. The filtrate (200 ml, light foam formation) was concentrated in the evaporator and dried in a desiccator (P2O5 as drying agent) at room temperature. Approximately 5.9 g of a colorless oil was obtained. 3. To 3.0 g of Lupasol G100 solution (used as such), 2.41 g of a-damascone was added. The mixture was stirred without using solvent. After stirring for 4 days, the obtained oil was dissolved in 100 ml of THF, dried with MgSO 4, filtered and the filtrate was concentrated on the rotary evaporator. After drying in the desiccator (P205) at room temperature, approximately 4.1 g of a colorless oil was obtained. This oil still contained approximately 13% (w / w) THF, even after prolonged drying (3 days).
The product obtained from the three procedures had identical NMR spectra. The ß-amino ketone was prepared from Lupasol P and a-damascone using the procedure described below: 1.8 g of Lupasol P solution was dissolved (50% H20, 50%
Lupasol PM 750000, obtained from BASF) in 7 ml of ethanol; the solution was stirred for a few minutes with a magnetic stirrer before adding 1.44 g of a-Damascona. After 3 days, the reaction mixture was filtered on a Celite filter (see above) and the residue was washed thoroughly with ethanol. After concentrating the filtrate and drying the oil obtained in the desiccator (P2O5) at room temperature, approximately 3 g of the reaction product between Lupasol and a-Damascona were obtained. In the following formulation examples, all levels are noted as% by weight of the composition, unless otherwise mentioned, and the incorporation of the amine reaction product hereinafter referred to as "ARP" in the composition completely formulated, is carried out by dry addition (d), encapsulation in starch (s), as described in GB-1, 464,616 or cyclodextrin (ec) or as in the composition as defined herein above. The term in parentheses for the ARP in the formulation examples refers to the means of incorporation. When none is provided, the incorporation is done as such. The levels given for ARP, whether processed or not, refer to the ARP level as if it were ARP processed or not.
EXAMPLE 1
The following fabric softening compositions are in accordance with the present invention:
EXAMPLE 2
The following fabric softener compositions aggregated in a dryer according to the invention were prepared:
EXAMPLE 3
The following fabric softening compositions according to the present invention were prepared:
EXAMPLE 4
The following fabric conditioning compositions added in a dryer were prepared according to the present invention:
EXAMPLE 5
The following are non-limiting examples of fabric conditioning compositions for pre-soaking and / or fabric improvement according to the present invention which can be used appropriately in the laundry rinse cycle.
EXAMPLE 6
The following are non-limiting examples of compositions for absorbing odors suitable for spray applications:
Claims (28)
1. - A reaction product between a primary and / or secondary amine-type compound and an active component that is selected from ketone, aldehyde and mixtures thereof; characterized in that said amine-type compound has a lower Odor Intensity Index than that of a 1% methyl anthranilate solution in dipropylene glycol, and the reaction product has a Dry Surface Odor number of more than 5; and with the proviso that said amine-type compound is not an amino-styrene.
2. A softening composition comprising a softening compound, a reaction product between a primary and / or secondary amine-type compound and an active component that is selected from ketone, aldehyde and mixtures thereof; characterized in that said amine-type compound has a lower Scent Intensity Index than that of a 1% methyl anthranilate solution in dipropylene glycol.
3. A composition according to claim 2, further characterized in that said amine-type reaction product has a Dry Surface Odor Index of more than 5.
4. A compound or a composition according to any of claims 1 to 3, further characterized in that said amine-type compound has the following empirical formula selected from: B- (NH2) n; B- (NH) n; and B- (NH) n- (NH2) n in which B is a carrier material, and each n is independently an index with a value of at least 1.
5. A compound or a composition in accordance with claim 4, further characterized in that said carrier material is selected from inorganic or organic carriers, and preferably is an organic carrier.
6. A compound or a composition according to claim 5, further characterized in that the inorganic carrier is a polydialkylsiloxane functionalized with amine.
7. A compound or a composition according to claim 5, further characterized in that said organic carrier material B having amine is selected from aminoaryl derivatives, polyamines, amino acids and their derivatives, amines and substituted amides, glucamines, dendrimers, mono-, di-, oligo- and polysaccharides substituted with amino, and / or mixtures thereof.
8. A compound or a composition according to claim 7, further characterized in that said aminoaryl derivatives are aminobenzene derivatives, preferably alkyl or aryl esters of 4-aminobenzoate compounds, preferably selected from ethyl 4-aminobenzoate, 4- phenylethyl aminobenzoate, phenyl 4-aminobenzoate, 4-amino-N '- (3-aminopropyl) benzamide, and mixtures thereof.
9. A compound or a composition according to claim 7, further characterized in that said polyamines are polyethyleneimines, 2,2,, 2"-triaminotriethylamine, 2,2'-diamino-diethylamine, 3,3'-diamino. -dipropylamine, 1,3-bis-aminoethylcyclohexane, poly [oxy (methyl-1,2-ethanediyl)], a- (2-aminomethylethyl) -? - (2-amino-methylethoxy) -, poly [oxy] (methyl- 1,2-ethanediyl), a-hydro-) -? - (2-amino-methyletoxy) -, ether with 2-ethyl-2- (hydroxymethyl) -1,3-propanediol, Stemamines C12, and mixtures of
10. A compound or a composition according to claim 7, further characterized in that said amine-type compounds are amino acids and their derivatives, preferably selected from tyrosine, tryptophan, lysine, glutamic acid, glutamine, aspartic acid, arginine. , asparagine, phenylalanine, proline, glycine, serine, histidine, threonine, methionine, ethylate or phenylester tyrosine, glycine methylate, ethylate or tryptophan phenyl ester, and mixtures thereof, preferably they are selected from tyrosine, tryptophan and mixtures thereof.
11. A compound or a composition according to claim 7, further characterized in that said amine-type compounds are amines and substituted amides, preferably selected from nipecotamide, N-coco-1, 3-propenediamine, N-oleyl-1,3-propeniamine, N- (tallowalkyl) -1, 3-propenedi amine, 1,4-diaminocyclohexane, 1,2 -diaminocyclohexane, 1,12-diaminododecane, and mixtures thereof.
12. A compound or a composition according to claim 7, further characterized in that said amine compounds are glucamines of formula H2N-CH2- (CH (OH)) x-CH2OH, wherein one or more OH functions may be substituted , and wherein x is an integer with a value of 3 or 4.
13. A compound or a composition according to claim 7, further characterized in that said amine-type compound is selected from polyamidoamine dendrimers, polyethylenimine dendrimers and / or polypropyleneimine, and diaminobutane polyamine DAB (PA) dendrimers x with x = 2nx4, and n is between 0 and 4, and / or mixtures thereof.
14. A compound or a composition according to claim 7, further characterized in that said amine-type compound is selected from amino-substituted monosaccharides in the acetal or ketal form of glucose, mannose, galactose and / or fructose; amino-substituted disaccharides in the acetal or ketal form of lactose, sucrose and / or cellobiose; oligosaccharides substituted with amino and / or amino substituted polysaccharides of cyclodextrin, chitosan, cellulose, starch, gueran, mannan and / or dextran; and / or the mixtures thereof.
15. A compound or a composition according to claim 14, further characterized in that said mono-, di-, oligo- or polysaccharide substituted with amino, is selected from aminoalginate, diaminoalginate, hexanediaminealginate, dodecanediaminealgiene, 6-amino-6- Deoxycellulose, O-ethylaminocellulose, O-methylamine-sucrose, 3-amino-3-deoxy-cellulose, 2-amino-2-deoxy-cellulose, 2,3-diamino-2,3-dideoxy-cellulose, 6- [N- (1,6-hexanediamine) ] -6-deoxycellulose, 6- [N- (1, 12-dodecanediamine)] - 6-deoxycellulose, o- [methyl- (N-1,6-hexanediamine)] cellulose, O- [methyl (N-1, 12-dodecanediamine)] cellulose, 2,3-di- [N- (1, 12-dodecanediamine)] ceIulose, 2,3-diamino-2,3-deoxy-alpha-cyclodextrin, 2,3-diamino-2, 3-deoxy-beta-cyclodextrin, 2,3-diamino-2,3-deoxy-gamma-cyclodextrin, 6-amino-6-deoxy-alpha-cyclodextrin, 6-amino-6-deoxy-beta-cyclodextrin, O- ethylamino-beta-cyclodextrin, 6 [N- (1,6-hexanediamino) -6-deoxy-alpha-cyclodextrin, 6 [N- (1,6-hexanediamino) -6-deoxy-beta-cyclodextrin, amino xtrane, N- [di- (1,6-hexanediamine)] dextran, N- [di- (1, 12-dodecanediamine)] dextran, 6-amino-6-deoxy-alpha-D-galactosyl-guaran, O- ethylaminoglorane, diaminooguarane, 6-amino-6-deoxy-starch, O-ethylaminostarch, 2,3-diamine-2,3-dideoxyalmidon, N- [6- (1,6-hexanediamine)] - 6-deoxyalm dón, N- [6- (1, 12-dodecanediamine)] - 6-deoxyalmidon, 2,3-di- [N- (1,6-hexanediamine)] - 2,3-dideoxyalmidon, and / or mixtures of the same.
16. A compound or a composition according to any of claims 2-15, further characterized in that said reaction product is previously formed before incorporating it into the fully formulated composition.
17. A composition according to any of claims 2-16, further characterized in that said reaction product is present in an amount of 0.001% to 10%, preferably 0.005% to 5%, and most preferred 0.01% to 2% by weight of the composition.
18. A compound or a composition according to any of claims 1-17, further characterized in that said active compound is selected from a flavoring ingredient of ketone or aldehyde type, a pharmaceutical active ingredient of ketone or aldehyde type, a agent for biological control of ketone or aldehyde type, a perfume component of ketone or aldehyde type, a cooling agent of ketone or aldehyde type and of mixtures thereof.
19. A reaction product or composition according to claim 1-18, further characterized in that said active component is a repellent for insects and / or moths, preferably selected from citronellal, citral, N, N-diethylmethaltoluamide, Rotundial 8- acetoxycarvotanacenone, and mixtures thereof.
20. A reaction product or composition according to claim 1-19, further characterized in that said active component is an antimicrobial, preferably selected from Glutaraldehyde, cinnamaldehyde, and mixtures thereof.
21. A compound or a composition according to claim 18, further characterized in that said active component is a perfume aldehyde, which is preferably selected from 1 -decanal, benzaldehyde, florhidral, 2,4-dimethyl-3-cyclohexen -1-carboxaldehyde, cis / trans-3,7-dimethyl-2,6-octadien-1 -al, heliotropin, 2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde, 2,6-nonadienal, aldehyde alpha-n-amylcinnamic, alpha-n-hexyl cinnamic aldehyde, PT Bucinal, liral, cimal, methylnonylacetaldehyde, hexanal, trans-2-hexenal, and mixtures thereof.
22. A compound or a composition according to claim 18, further characterized in that said active component is a perfume ketone that is preferably selected from Alfa-Damascona, Delta-Damascone, Iso-Damascone, Carvone, Gamma-Methionone, Iso-E-Super, 2,4,4,7-Tetramethyl-Oct-6-En-3-Ona, Benzylacetone, Beta Damascone, Damascenone, Methyldihydrojasmonate, methylredrilone, and mixtures thereof.
23. A compound or a composition according to claim 18, further characterized in that said perfume has an Odor Detection Threshold less than or equal to 1 ppm, preferably less than or equal to 10 ppb.
24. A compound or a composition according to claim 23, further characterized in that said perfume is selected from undecylenic aldehyde, gamma-undecalactone, heliotropin, gamma-dodecalactone, p-anisic aldehyde, para-hydroxy-phenyl-butanone, cimal , benzylacetone, alpha-ionone, pt bucinal, damascenone, beta-ionone and methyl-nonyl-ketone, and mixtures thereof.
25. A method of delivering residual fragrance to a surface, comprising the steps of contacting said surface with a reaction product between a primary and / or secondary amine compound and an active component selected from an aldehyde. or a ketone and mixtures or composition thereof as defined in any of claims 1-24, and then contacting the treated surface with a material, so that the amine-type reaction product is released.
26. A method according to claim 25, further characterized in that said material is water.
27. The use of a compound as defined in any of claims 1-15 or 18-24, for the manufacture of a composition for supplying residual active compound on a surface on which it is applied.
28. The use according to claim 27, wherein said surface is a fabric.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP98870156.1 | 1998-07-10 | ||
EP98870227 | 1998-10-28 |
Publications (1)
Publication Number | Publication Date |
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MXPA01000365A true MXPA01000365A (en) | 2001-09-07 |
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