MXPA99002627A - Polymeric compound comprising one or more active alcohols - Google Patents
Polymeric compound comprising one or more active alcoholsInfo
- Publication number
- MXPA99002627A MXPA99002627A MXPA/A/1999/002627A MX9902627A MXPA99002627A MX PA99002627 A MXPA99002627 A MX PA99002627A MX 9902627 A MX9902627 A MX 9902627A MX PA99002627 A MXPA99002627 A MX PA99002627A
- Authority
- MX
- Mexico
- Prior art keywords
- group
- polymer
- composition
- further characterized
- mixtures
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 53
- 150000001298 alcohols Chemical class 0.000 title description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 66
- 229920000642 polymer Polymers 0.000 claims abstract description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 39
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims abstract description 13
- 230000003111 delayed Effects 0.000 claims abstract description 10
- 125000004185 ester group Chemical group 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 157
- 235000019441 ethanol Nutrition 0.000 claims description 70
- -1 ethylene, 1,2-propylene, 1,3-propylene Chemical group 0.000 claims description 54
- 229920002873 Polyethylenimine Polymers 0.000 claims description 40
- 239000004744 fabric Substances 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 31
- 229920000768 polyamine Polymers 0.000 claims description 29
- 239000002304 perfume Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 20
- 238000004140 cleaning Methods 0.000 claims description 18
- KDPAWGWELVVRCH-UHFFFAOYSA-M 2-bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 claims description 17
- 102000004190 Enzymes Human genes 0.000 claims description 16
- 108090000790 Enzymes Proteins 0.000 claims description 16
- 239000003599 detergent Substances 0.000 claims description 16
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 14
- 229940088598 Enzyme Drugs 0.000 claims description 14
- 150000002829 nitrogen Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 8
- 108010059892 Cellulase Proteins 0.000 claims description 8
- 239000005792 Geraniol Substances 0.000 claims description 8
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 8
- 229930008393 geraniol Natural products 0.000 claims description 8
- 229940113087 geraniol Drugs 0.000 claims description 8
- GLZPCOQZEFWAFX-JXMROGBWSA-N β-Geraniol Chemical compound CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 claims description 8
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 229920001002 functional polymer Polymers 0.000 claims description 7
- 229930007744 linalool Natural products 0.000 claims description 7
- 229940106157 CELLULASE Drugs 0.000 claims description 6
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinylpyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 claims description 5
- 229930008394 dihydromyrcenol Natural products 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- RRAFCDWBNXTKKO-UHFFFAOYSA-N Eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N Phenethyl alcohol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 4
- MWOOGOJBHIARFG-UHFFFAOYSA-N Vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 4
- 229930004021 citronellol Natural products 0.000 claims description 4
- 235000000484 citronellol Nutrition 0.000 claims description 4
- 229920001661 Chitosan Polymers 0.000 claims description 3
- 229940089960 Chloroacetate Drugs 0.000 claims description 3
- QCDWFXQBSFUVSP-UHFFFAOYSA-N Phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 3
- 229960005323 Phenoxyethanol Drugs 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 claims description 3
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 claims description 3
- 229920002717 polyvinylpyridine Polymers 0.000 claims description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 2
- XGRCZWYTJSFHET-UHFFFAOYSA-N (2,4-dimethylcyclohex-3-en-1-yl)methanol Chemical compound CC1C=C(C)CCC1CO XGRCZWYTJSFHET-UHFFFAOYSA-N 0.000 claims description 2
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 claims description 2
- OXYRENDGHPGWKV-UHFFFAOYSA-N 3-methyl-5-phenylpentan-1-ol Chemical compound OCCC(C)CCC1=CC=CC=C1 OXYRENDGHPGWKV-UHFFFAOYSA-N 0.000 claims description 2
- UFLHIIWVXFIJGU-ARJAWSKDSA-N Cis-3-Hexen-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 claims description 2
- 239000005770 Eugenol Substances 0.000 claims description 2
- 229960002217 Eugenol Drugs 0.000 claims description 2
- CRDAMVZIKSXKFV-YFVJMOTDSA-N Farnesol Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CO CRDAMVZIKSXKFV-YFVJMOTDSA-N 0.000 claims description 2
- 229940043259 Farnesol Drugs 0.000 claims description 2
- 229960004873 LEVOMENTHOL Drugs 0.000 claims description 2
- 229940041616 Menthol Drugs 0.000 claims description 2
- 229940067107 Phenylethyl Alcohol Drugs 0.000 claims description 2
- WUOACPNHFRMFPN-UHFFFAOYSA-N Terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 claims description 2
- 229940116411 Terpineol Drugs 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229930002886 farnesol Natural products 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- 235000012141 vanillin Nutrition 0.000 claims description 2
- 229940117960 vanillin Drugs 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- 239000007844 bleaching agent Substances 0.000 description 35
- 150000002148 esters Chemical group 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 239000002585 base Substances 0.000 description 25
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 23
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 20
- 239000012190 activator Substances 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 18
- 239000011780 sodium chloride Substances 0.000 description 18
- 230000002194 synthesizing Effects 0.000 description 18
- 239000007788 liquid Substances 0.000 description 16
- 235000014113 dietary fatty acids Nutrition 0.000 description 14
- 239000000194 fatty acid Substances 0.000 description 14
- 239000004615 ingredient Substances 0.000 description 14
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 108010094020 polyglycine Proteins 0.000 description 12
- 229920000232 polyglycine polymer Polymers 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 229910000323 aluminium silicate Inorganic materials 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000002431 hydrogen Chemical group 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 229920005646 polycarboxylate Polymers 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- BPQQTUXANYXVAA-UHFFFAOYSA-N silicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 235000011187 glycerol Nutrition 0.000 description 9
- 229960005150 glycerol Drugs 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229920000223 polyglycerol Polymers 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 230000000875 corresponding Effects 0.000 description 7
- 239000003760 tallow Substances 0.000 description 7
- UKMSUNONTOPOIO-UHFFFAOYSA-N Behenic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 6
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 229940027983 antiseptics and disinfectants Quaternary ammonium compounds Drugs 0.000 description 6
- NOWKCMXCCJGMRR-UHFFFAOYSA-N aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 6
- 229960003237 betaine Drugs 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- 239000010457 zeolite Substances 0.000 description 6
- KOWCUAVOQZQRRN-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl 2-chloroacetate Chemical compound CC(C)=CCCC(C)(C=C)OC(=O)CCl KOWCUAVOQZQRRN-UHFFFAOYSA-N 0.000 description 5
- 108010084185 Cellulases Proteins 0.000 description 5
- 102000005575 Cellulases Human genes 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 238000004061 bleaching Methods 0.000 description 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- 230000002829 reduced Effects 0.000 description 5
- 150000004760 silicates Chemical class 0.000 description 5
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 5
- MLMGJTAJUDSUKA-UHFFFAOYSA-N 2-ethenyl-1H-imidazole Chemical compound C=CC1=NC=CN1 MLMGJTAJUDSUKA-UHFFFAOYSA-N 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 235000010582 Pisum sativum Nutrition 0.000 description 4
- 239000004115 Sodium Silicate Substances 0.000 description 4
- NTHWMYGWWRZVTN-UHFFFAOYSA-N Sodium silicate Chemical class [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 4
- 239000004902 Softening Agent Substances 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000005466 alkylenyl group Chemical group 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000007046 ethoxylation reaction Methods 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920000120 polyethyl acrylate Polymers 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 235000019832 sodium triphosphate Nutrition 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 238000007056 transamidation reaction Methods 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WSEBKJRVPMLGFV-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-(2-hydroxyethyl)-dimethylazanium;chloride Chemical compound [Cl-].OCC[N+](C)(C)CC(O)CCl WSEBKJRVPMLGFV-UHFFFAOYSA-M 0.000 description 3
- WLDGDTPNAKWAIR-UHFFFAOYSA-N 1,4,7-trimethyl-1,4,7-triazonane Chemical compound CN1CCN(C)CCN(C)CC1 WLDGDTPNAKWAIR-UHFFFAOYSA-N 0.000 description 3
- 235000021357 Behenic acid Nutrition 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 235000021360 Myristic acid Nutrition 0.000 description 3
- 206010033546 Pallor Diseases 0.000 description 3
- 108091005771 Peptidases Proteins 0.000 description 3
- 241000219843 Pisum Species 0.000 description 3
- 239000004365 Protease Substances 0.000 description 3
- 102000014961 Protein Precursors Human genes 0.000 description 3
- 108010078762 Protein Precursors Proteins 0.000 description 3
- JNYAEWCLZODPBN-CTQIIAAMSA-N Sorbitan Chemical class OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 230000000443 biocontrol Effects 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 239000003093 cationic surfactant Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940042397 direct acting antivirals Cyclic amines Drugs 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002314 glycerols Chemical class 0.000 description 3
- 229920000591 gum Polymers 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000000670 limiting Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000006011 modification reaction Methods 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 150000003138 primary alcohols Chemical class 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000001187 sodium carbonate Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 229910052911 sodium silicate Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 229960002920 sorbitol Drugs 0.000 description 3
- 235000011044 succinic acid Nutrition 0.000 description 3
- CIOXZGOUEYHNBF-UHFFFAOYSA-N (carboxymethoxy)succinic acid Chemical compound OC(=O)COC(C(O)=O)CC(O)=O CIOXZGOUEYHNBF-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-Propanediol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- CFPOJWPDQWJEMO-UHFFFAOYSA-J 2-(1,2-dicarboxylatoethoxy)butanedioate Chemical compound [O-]C(=O)CC(C([O-])=O)OC(C([O-])=O)CC([O-])=O CFPOJWPDQWJEMO-UHFFFAOYSA-J 0.000 description 2
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2H-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N 3-(2,3-dihydroxypropoxy)propane-1,2-diol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- FAGGUIDTQQXDSJ-UHFFFAOYSA-N 3-benzoylazepan-2-one Chemical compound C=1C=CC=CC=1C(=O)C1CCCCNC1=O FAGGUIDTQQXDSJ-UHFFFAOYSA-N 0.000 description 2
- 108010065511 Amylases Proteins 0.000 description 2
- 102000013142 Amylases Human genes 0.000 description 2
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- 150000004685 tetrahydrates Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- PODBBOVVOGJETB-UHFFFAOYSA-N zinc phthalocyanine Chemical class N1=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N33)=[N]2[Zn]23N3C1=C1C=CC=CC1=C3N=C1[N]2=C4C2=CC=CC=C21 PODBBOVVOGJETB-UHFFFAOYSA-N 0.000 description 1
Abstract
The present invention relates to polymers containing at least one nitrogen atom, wherein at least one of the nitrogen atoms is linked to an ester group, said ester group bearing an active alcohol. By the present invention, a delayed release of the active alcohol is provided upon contact of the compound with an aqueous medium.
Description
POLYMERIC COMPOSITE THAT COMPRISES ONE OR MORE ACTIVE ALCOHOLS
FIELD OF THE INVENTION
The present invention relates to polymeric compounds comprising one or more active alcohols. More particularly, it relates to amino functional polymeric compounds comprising one or more active alcohols suitable for use in cleaning and laundry products.
BACKGROUND OF THE INVENTION
Cleaning and laundry products are well known in the art. However, the acceptance of these products by the consumer is determined not only by the performance achieved with these products, but also by the aesthetics associated with them. The perfume components are therefore an important aspect in the successful formulation of such commercial products. Accordingly, the formulation of compounds that provide the delayed release of perfume for a longer period than by the use of the perfume itself has been provided. The description of said compounds can be found in WO 95/04809, WO 95/08976 and pending application EP 95303762.9. The latter describes betaine ester compounds of perfume alcohols that provide for the release of the perfume components over a long period. The Applicant has now found that polymers containing one or more nitrogen atoms to which an ester function is attached, to provide an N-polymeric ester of betaine and / or amino ester of an active alcohol, also provide the delayed release of active alcohol such as a perfume. Another advantage of the present invention is that the polymeric group provides sufficient stabilization of the ester function, so that the release of the active alcohol after storage in the product is limited, without preventing the release of the active alcohol with the use of the product.
BRIEF DESCRIPTION OF THE INVENTION
The present invention relates to a polymer containing at least one nitrogen atom, wherein at least one of the nitrogen atoms is attached to an ester group of the formula:
where each R'i, R'2 > independently, it is selected from hydrogen, hydroxyl, alkyl group, alkylene group, aryl group, alkylaryl, or any other chain containing at least one carbon atom, where n3 is an integer that is on the scale of 1 to 3, and wherein R is an organic chain of an active alcohol. The present invention also encompasses cleaning and laundry compositions incorporating said polymeric compound. In another aspect of the invention, there is provided a method for providing the delayed release of an active alcohol, comprising the step of contacting materials that will be treated with an aqueous medium comprising a compound or composition of the invention. In a further aspect of the invention, there is provided a process for preparing a polymeric ether compound of the invention, by reacting a polyamino-functional polymer with a bromoacetate and / or chloroacetate of an active alcohol in the presence of a non-hydroxylated solvent.
DETAILED DESCRIPTION OF THE INVENTION
Polymer Compound The essential component of the invention is a polymer containing at least one nitrogen atom, wherein at least one of the nitrogen atoms is attached to an ester group of the formula:
wherein each R'-i, R'2I independently, is selected from hydrogen, hydroxyl, alkyl group, alkylene group, aryl group, alkylaryl, or any other chain containing at least one carbon atom, wherein n3 is a whole which is on the scale of 1 to 3, preferably n3 is an integer of value 1, and where R is an organic chain of an active alcohol. The different groups for R'i, R'2 can be substituted or not substituted. Preferably, each R'i, R'2, independently, is selected from hydrogen, alkyl group, aryl group, - (CH2) m -COOH, - (CH2) m-COOR, - (CH2) m-OH, - ( CH2) mO (O) CR ', where each m, independently, is an integer of value 0, 1 or 2, and each m ', independently, is an integer of value 1, 2 or 3, and R' is an alkyl group containing from 1 to 19 carbon atoms. More preferably, each R'1, R'2 is independently selected from hydrogen, methyl group, aryl group, and most preferably is hydrogen. Polymers suitable for use herein generally have a molecular weight less than 100,000, preferably between 300 and 100,000, more preferably between 500 and 10,000, and most preferably between 500 and 5,000. The polymer can be of any type, including copolymer, homopolymers, terpolymer, or mixtures of either monomer as long as at least one nitrogen atom is present within the polymer. The nitrogen atom having the ester function containing the active alcohol can be located in any position, ie, in the base structure and / or side chain. Preferred polymers suitable for use herein are amino functional polymers selected from polyamines, polyvinylpyridines, poly (vinylpyrrolidone / vinylimidazole) copolymers, polymers having pyrolidine rings, polyvinylimidazoles, chitosans, and mixtures thereof, preferably polymers of polyamine The polymer can be linear or branched, but is preferably branched. Polyamine polymers suitable for use herein are selected from a) linear or non-cyclic polyamines having a base structure of the formula: H [H2N-R '] n + 1- [N-RV [N-R '] n-NH2
b) cyclic polyamines having a base structure of the formula: H R '[H2N-R'] n.k + 1 - [N-R '] m - [N-Rl n- [N-R1] k- NH2
c) polyamines having a base structure of the formula:
I NH2
and mixtures thereof; wherein R 'is C2-C8alkylene, alkylene substituted with C3-C8alkyl, and mixtures thereof; preferably R 'is ethylene, 1,2-propylene, 1,3-propylene, and mixtures thereof, more preferably ethylene. The units R 'serve to join the nitrogens of the amine of the base structure; where m is from 2 to 700; n is from 0 to 350; and is from 5 to 10,000, preferably from 10 to 5,000, more preferably from 20 to 5,000. Preferably, the polyamines have a m: n ratio of at least 1: 1, but can include linear polymers (n equal to 0), as well as a scale as high as 10: 1, preferably the ratio is 2: 1. When the ratio of m: n is 2: 1, the ratio of primary amine: secondary: tertiary, that is, the ratio of portions -R'Nhb, -R'NH and -R'N, is 1 : 2: 1 Preferred polyamines for use herein comprise base structures wherein less than 50% of the R 'groups comprise more than 3 carbon atoms; more preferably, they comprise less than 25% portions having more than 3 carbon atoms, and more preferred base structures comprise less than 10% portions having more than 3 carbon atoms. Polyamines for use herein include homogeneous or non-homogeneous base structures of polyamine, preferably homogeneous base structures. For the purposes of the present invention, the term "homogeneous polyamine base structure" is defined as a polyamine base structure having R 'units that are the same (ie, all ethylene). However, this equality of definition does not exclude polyamines comprising other foreign units that comprise the polymer base structure that are present due to an artifact of the selected chemical synthesis method. For example, it is known to those skilled in the art that ethanolamine can be used as an "initiator" in the synthesis of polyethylene imines; therefore, a polyethylenimine sample comprising a hydroxyethyl portion resulting from the polymerization initiator would be considered to comprise a homogeneous polyamine base structure for the purposes of the present invention. For the purposes of the present invention, the term "non-homogeneous polymer base structure" refers to polyamine base structures that are a complex of one or more substituted alkylene or alkylene moieties, for example, ethylene units and of 1, 2-propylene considered together as R 'units. Other polyamines comprising the base structure mentioned above are generally polyalkyleneamines (PAA's), polyalkyleneimines (PAI's), preferably polyethyleneamine (PEA's) or polyethyleneimines (PEI's). A common polyalkyleneamine (PAA) is tetrabutylenepentamine. PEAs are obtained by reactions involving ammonia and ethylene dichloride, followed by fractional distillation. The common PEA's obtained are triethylenetetramine (TETA) and tetraethylenepentamine (TEPA). The above pentaamines, ie hexamines, heptamines, octamines and possibly nonamines, the cogenically derived mixture does not appear to be separated by distillation, and may include other materials such as cyclic amines and particularly piperazines. Also included are cyclic amines with side chains in which nitrogen atoms appear to be present. See the patent of E.U.A. 2,792,372, Dickinson, issued May 14, 1957, which describes the preparation of PEA's. PEIs comprising the preferred base structures of the polyamines of the present invention can be prepared, for example, by polymerizing ethylene imine in the presence of a catalyst such as carbon dioxide, sodium bisulfite, sulfuric acid, hydrogen peroxide, hydrochloric acid, acetic acid, etc. Specific methods for preparing PEI's are described in the US patent 2,182,306, Ulrich et al., Issued December 5, 1939; patent of E.U.A. 3,033,7465, Mayle et al., Issued May 8, 1962; patent of E.U.A. 2,208,095, Esselmann et al., Issued July 16, 1940; patent of E.U.A. 2,806,839, Crowther, issued September 17, 1957; and the patent of E.U.A. 2,553,696, Wilson, issued May 21, 1951 (all incorporated herein by reference). In addition to the linear and branched PEI's, the present invention also includes cyclic amines that are typically formed as synthesis artifacts. The presence of these materials can be increased or decreased depending on the conditions selected by the formulator. Commercially available polyamines suitable for use herein are poly (ethylenimine) with PM 1200, hydroxyethylated poly (ethylenimine) from Polysciences, with MW 2000; 80% hydroxyethylated poly (ethyleneimine) from Aldrich; and poly (ethyleneimine) (MW 1800) marketed under the trade name of Epomin SP-018 by Nippon Shokubai. Polyvinylimidazoles as well as copolymers of poly (vinylpyrrolidone / vinylimidazole) suitable for use herein are described in DE 2814287. Preferably, the copolymers of poly (vinylpyrrolidone / vinylimidazole) have a molar ratio of N-vinylimidazole: N- vinylpyrrolidone of 1: 0.2, more preferably 0.8: 0.3, most preferably 0.6: 04. Copolymers of poly (vinylpyrrolidone / vinylimidazole) suitable for use herein are also commercially available from BASF. Polyvinylpyridines and chitosan are commercially available from Aldrich. The above polymers can also be partially modified. For the purposes of the present invention, the term "modification", in relation to the chemical structure of the polymer, is defined as the replacement of a nitrogen atom of -NH from the base structure or side chain by an R unit. "(substitution), the quaternization of the nitrogen of a base structure (quaternized), or the oxidation of nitrogen from a base structure to the N-oxide (oxidized)." The terms "modification" and "substitution" are used interchangeably when reference is made to the process for replacing a nitrogen atom attached to a nitrogen atom of the base structure with an R "unit. The alkoxylation or oxidation may occur in some circumstances without substitution, but the substitution is preferably accompanied by oxidation or ethoxylation of at least one nitrogen of the base structure or of the side chain. By "partially modified" it is meant that at least one NH unit is still present after the modification, so that it can be subsequently bonded by chemical reaction with the aforementioned ester function having the active alcohol group. The R "units are selected from the group consisting of hydrogen, C-1-C22 alkyl, C3-C22 alkenyl, C7-C22 arylalkyl C2-C22 hydroxyalkyl, - (CH2) PCO2M, (CH2) qSO3M, - CH (CH2CO2M) CO2M, - (CH2) PO3M or - (R1O) xB, -C (O) R3, wherein R1 is selected from the group consisting of C2-C6 alkylene, C3-C6 alkyl-substituted alkylene, and mixtures thereof: R3 is selected from the group consisting of C1-C18 alkyl, C7-C12 arylalkyl, aryl substituted with C7-C12 alkyl, C6-C12 aryl, and mixtures thereof; of the group consisting of hydrogen, d-C6 alkyl - (CH2) qSO3M, - (CH2) PCO2M, (CH2) q (CHSO M) CH2SO3M, - (CH2) q- (CHSO2M) CH2S? 3M, - (CH2 ) PO3M or
PO3M, and mixtures thereof; M is hydrogen or a water-soluble cation in sufficient quantity to satisfy the charge balance; X is a water-soluble anion; m has the value of 2 to 700; n has the value from 0 to 350; k is less than n or equal to it; 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; and z has the value of 0 or 1. Preferably, x has a value of 1 to 20, more preferably 1 to 10. Preferred R "units are selected from the group consisting of C1-C22 alkylene, (R1O) xB, -C (O) R3, - (CH ") pCO2M, - (CH2) qSO3M, -CH (CH2C? 2M) C? 2M, preferably C1-C22 alkylene, - (10) xB and -C (O) R3 , and most preferably (R1O) xB. Preferably, R1 is selected from the group consisting of C? -C? Alkylene, C3-C6 alkyl substituted alkylene, and mixtures thereof, more preferably R1 is ethylene. Preferably, R3 is selected from the group consisting of C1-C12 alkyl, C7-C12 alkylarylene, and mixtures thereof, more preferably R3 is selected from the group consisting of C2-C2 alkyl, and mixtures thereof, and most preferably R3 is selected from the group consisting of Ci-Cß alkyl, and mixtures thereof. A most preferred group for R3 is methyl. Preferably, the units B are selected from the group consisting of hydrogen, C6 alkyl, - (CH2) qSO3M, - (CH2) q (HSO3M) CH2SO3M or .- (CH2) q (CHSO2M) -CH2SO3M, and mixtures of them, more preferably B is selected from the group consisting of hydrogen, - (CH2) qSO3M, - (CH2) q (CHSO3M) CH2SO3M or (CH2) q (CHSO2M) -CH2S? 3M, and mixtures thereof, and most preferably B is selected from the group consisting of hydrogen, wherein q has the value of 0 to 3. Among the polymers described above, the most preferred polymer is a branched polyethylene imine of molecular weight between 500 and 5000, preferably partially ethoxylated with 0.25. to 0.75 moles of ethylene oxide per mole of nitrogen in the polymer. For the compounds mentioned above, the R group is the organic chain of an active alcohol. By "organic chain" is meant any chain containing at least one carbon atom. Preferably the active alcohol is selected from a flavoring alcohol ingredient, a pharmaceutical alcohol active agent, a biocontrol alcohol agent, a perfume alcohol component, and mixtures thereof. When more than one R group is present in the polymeric compound of the invention, each R group may be different from the others, for example, when there are two R groups, one may be a biocontrol alcohol agent, and the other a component of perfume alcohol, or one R is a component of perfume alcohol and the other group R a different perfume alcohol component. Flavoring ingredients include spices, flavor enhancers that contribute to the overall perception of flavor.
Pharmaceutical active agents include drugs. Biocontrol agents include biocides, antimicrobials, bactericides, fungicides, algicides, mildew, disinfectants, antiseptics, insecticides, vermicides and growth hormones. Perfume alcohol components include components that have odoriferous properties. Preferably, for the compounds mentioned above, the R group is the organic chain of a perfume alcohol, said alcohol being selected from 2-phenoxyethanol, phenyl ethyl alcohol, geraniol, citronellol, 3-methyl-5-phenyl-1-pentanol, 2,4-dimethyl-3-cyclohexen-1-methanol, linalool, tetrahydrolinalool, 1,2-dihydromyrcenol, hydroxy citronellal, farnesol, menthol, isopulegol, eugenol, vanillin, cis-3-hexenol, terpineol, and mixtures thereof. Preferred R groups for the purposes of the invention are the organic chains of active alcohol selected from geraniol, citronellol, linalool and dihydromyrcenol. The polymeric compound to be used herein is polyglycine and / or perfume alcohol polybetaine. By the term polyglycine it is understood that the nitrogen atoms attached to the ester groups of the active alcohol are not quaternized; and by the term polybetaine it is understood that the nitrogen atoms attached to the ester groups of the active alcohol are quaternized. The nitrogen atom having the active alcohol function can also have other substituents on its remaining positions. Preferred substituents are those selected from hydrogen, alkyl,
alkylene or aryl.
R'i R'l L kJn R'1 - [c] n3 - C OR RO - [c] n3- N- ÍC] - G- OR
R'2 O O R'2 R'2 and
OR
(n2 + 1) A wherein each R-i, R2, independently, is selected from hydrogen, alkyl group, aryl group; where each n, n1, independently, is an integer that is on the scale of 1 to 20, where n2 is an integer that is on the scale of 1 to 6, and where n3 is as defined above. For the purposes of the invention, mixtures of the above polymeric compounds comprising one or more active alcohols can also be used.
Release Mechanism By the present invention, the delayed release of an active alcohol is obtained. Unless limited by theory, it is thought that the release occurs by the following mechanism: where the nitrogen atom is in a protonated form to form a betaine ester, the release of the active alcohol is obtained by hydrolysis of the betaine ester, such as occurs after coming into contact with water or ambient humidity; where the nitrogen possessing the ester of an active alcohol is in non-protonated form, the nitrogen atom is converted to a protonated form after the pH is lowered to become a betaine, and then provides the release of the active alcohol. The pH decrease can occur, for example, by dilution of the compound in water. Accordingly, when the polymeric compound contains protonated nitrogen atoms possessing the ester of an active alcohol as well as non-protonated nitrogen atoms possessing the ester of an active alcohol, such as occurs when the polymeric compound is a partially quaternized polymer, it is you can get a different delayed release rate: betaine first releases your active alcohol, while the amino acid releases its active alcohol only after you convert it to its betaine form.
Procedure The preparation of the component is carried out in the following manner in the synthesis examples. A preferred process for preparing polymeric compounds comprising one or more active alcohols is by reacting an amino-functional polymer such as a polyamine component with a bromoacetate and / or chloroacetate of an active alcohol in the presence of a non-hydroxylated solvent such as chloroform, acetonitrile, acetone, ethyl acetate, or mixtures thereof, preferably chloroform and / or ethyl acetate. An advantage of the present method is that transamidation and / or even transesterification, when the polymeric compound is partially ethoxylated, are limited. In addition, transesterification / transamidation are some of the problems that occur during the preparation of the polymeric compounds of the invention. Said transesterification / transamidation leads to the degradation of some ester bonds of the perfume alcohol, and to the subsequent release of the free perfume alcohol during the course of the reaction process. Accordingly, by the use of a non-hydroxylated solvent, the degree to which these side reactions occur is limited. For example, when the present process is used, by reacting polyethyleneimine PM1800, ethoxylated with 0.5 moles of ethylene oxide and geranyl bromoacetate in chloroform, the transesterification is limited to less than 20%, preferably less than 10% by moles of the material of starting from geranyl bromoacetate. It will also be apparent to the person skilled in the art that when a PEI is reacted with a bromoacetate of an active alcohol, only the transamidation is observed as a secondary reaction. Another process, which may be suitable for use herein to prepare the polymeric compounds of the invention, is to first prepare a polyamnomethyl ester or a polyaminoethyl ester. The polyamnomethyl ester or polyaminoethyl ester can be prepared by reacting a bromine ester or a chlorine ester (such as methyl bromoacetate or methyl chloroacetate), methyl bromopropanoate or methyl chloropropanoate) with a polyamino-functional polymer. In a second step, the polyamine methyl ester (such as polyglycine methyl ester or polyethamine methyl ester) or the polyaminoethyl ester are transesterified with an active alcohol (such as a perfume alcohol) in the presence of a catalytic to stoichiometric amount of sodium methoxide. sodium or sodium. For example, a geraniol polyglycine ester can be prepared by first reacting methyl chloroacetate with a polyethylene imine, and then transesterifying the intermediate polyglycine methyl ester with geraniol, using a catalytic amount of sodium methoxide.
Laundry Cleaning and Composition Compositions The compositions of the present invention include cleaning and laundry compositions which are typically used to wash fabrics and clean hard surfaces such as tableware, floors, bathrooms, toilets, kitchens and other surfaces that need to be cleaned and / or disinfected, but also for use in personal cleansing such as bath gels, deodorants, bars and shampoos. Laundry compositions resulting from contacting the polymeric ester compound of the invention with the fabrics are preferred. Preferably for use in cleaning and laundry products, the active alcohol is a perfume, such as geraniol. It should be understood that these compositions include not only detergent compositions that provide fabric cleaning benefits, but also compositions such as fabric softener compositions added during rinsing and compositions added to the dryer (eg, sheets), which provide softening benefits. and / or antistatic, as well as hard surface cleaning. The polymeric ester compounds typically comprise from 0.01% to 10%, preferably from 0.05% to 5%, and more preferably from 0.1% to 2%, by weight of the composition. Mixtures of polymeric ester compounds can also be used herein. Optional ingredients useful for formulating said cleaning and laundry compositions in accordance with the present invention include one or more of the following.
Fabric softening agents A fabric softening component can also be conveniently used in the cleaning and laundry compositions of the invention to provide soft and antistatic properties to the treated fabrics. When used, the fabric softening component will typically be present at a level sufficient to provide softening and antistatic properties. Said fabric softening component may be selected from cationic, nonionic, amphoteric or anionic fabric softening component. Typical preferred cationic fabric softening components include the water-insoluble quaternary ammonium fabric softening actives, most commonly having used long alkyl chain ammonium dichloride or methyl sulfate. Preferred cationic softeners include the following: 1) ditallow dimethyl ammonium chloride (DTDMAC); 2) dihydrogenated sebodimethylammonium chloride;
3) dihydrogenated sebodimethylammonium methylsulfate; 4) distearyldimethylammonium chloride; 5) dioleyldimethylammonium chloride; 6) dipalmitylhydroxyethylmethyl ammonium chloride; 7) stearylbenzyldimethylammonium chloride; 8) sebotrimethylammonium chloride; 9) hydrogenated sebotrimethylammonium chloride; 10) alkylhydroxyethyldimethylammonium chloride of C < 2-14) 11) alkyldihydroxyethylmethylammonium chloride of C < 2-18; 12) di (stearoyloxyethyl) dimethylammonium chloride (DSOEDMAC); 13) di (tallowoyloxyethyl) dimethylammonium chloride); 14) diseboimidazolinium methylsulfate; 15) 1- (2-tallowamemidoethyl) -2-tallowyl imidazolinium methylsulfate. However, in recent years, the need for less environmentally aggressive materials has grown, and rapidly biodegradable quaternary ammonium compounds have been presented as alternatives to traditionally used dialkyl long chain methanesulfonates and ammonium chlorides. Such materials and fabric softening compositions containing them are described in numerous publications such as EP-A-0,040,562 and EP-A-0,239,910. The quaternary ammonium compounds and amine precursors of the present have the formula (I) or (II), below:
X '
(H)
wherein Q is selected from -O-C (O) -, -C (O) -O-, -O-C (O) -O-, NR -C (O) -, C (O) -NR4-; R1 is (CH2) n-Q-T2 or T;
R2 is (CH2) m-Q-T4 or T $ or T;
R3 is C1-C4 alkyl or C1-C4 hydroxyalkyl or H;
R 4 is H or C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl;
T1, T2, T3, T4 and T5 are independently alkyl or alkenyl of C- | 1-C22; n and m are integers from 1 to 4; and X "is an anion compatible with softener. Non-limiting examples of anions compatible with softener include chloride or methyl sulfate.
The chain T1, T2, T3, T4 and T5 of the alkyl or alkenyl must contain at least 11 carbon atoms, preferably at least 16 carbon atoms. The chain can be straight or branched. Sebum is a convenient and inexpensive source of long chain alkyl and alkenyl material. Particularly preferred are compounds in which T1, T2, T3, T4 and T ^ represent the mixture of long chain materials typical for tallow. Specific examples of quaternary ammonium compounds suitable for use in the aqueous fabric softening compositions herein include: 1) N, N-di (tallowyloxyethyl) -N, N-dimethylammonium chloride; 2) N, N-di (tallowyloxyethyl) -N-methyl, N- (2-hydroxyethyl) ammonium methyl sulfate; 3) N, N-di (2-tallowyl-oxy-2-oxo-ethyl) -N, N-dimethylammonium chloride; 4) N, N-di (2-tallowyl-oxy-ethylcarbonyl-oxy-ethyl) -N, N-dimethylammonium chloride; 5) N- (2-tallowyl-oxy-2-ethyl) -N- (2-tallowyl-oxy-2-oxo-ethyl) -N, N-dimethylammonium chloride; 6) N, N, N-tri (tallowyloxyethyl) -N-methylammonium chloride; 7) N- (2-tallowyl-oxy-2-oxoethyl) -N- (tallowyl-N, N-dimethylammonium chloride, and 8) 1,2-difayoxy-oxy-3-trimethylammoniopropane chloride, and mixtures of any of the above materials.
Of these, compounds 1-7 are examples of compounds of formula (I), and compound 8 is a compound of formula (II). Particularly preferred is N, N-di (tallowyloxyethyl) -N, N-dimethylammonium chloride, wherein the tallow chains are at least partially unsaturated. The level of unsaturation of the sebum chain can be measured by the Iodine (IV) value of the corresponding 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 below or above 25. In fact, for compounds of the formula (I) made from tallow fatty acids having an IV of 5 to 25, preferably 15 to 20, it has been found that a cis / trans isomer weight ratio of more than 30/70, preferably more than 50/50 and most preferably more than 70/30 provides optimum concentration capacity. For compounds of the formula (I) made from tallow fatty acids having an IV of more than 25, it has been found that the ratio of cis to trans isomers is less critical unless very high concentrations are required. Other examples of suitable quaternary ammoniums of the formula
(I) and (II) are obtained, for example: by replacing "tallow" in the above compounds with, for example, coconut, palm, lauryl, oleyl, ricinoleyl, stearyl, palmityl or the like, said fatty acyl chains being or completely saturated or preferably at least partially unsaturated; replacing "methyl" in the above compounds with ethyl, ethoxy, propyl, propoxy, isopropyl, butyl, isobutyl or t-butyl; replacing "chloride" in the above compounds with bromide, methylsulfate, formate, sulfate, nitrate and the like. In fact, the anion is present merely as a counter-ion of the positively charged quaternary ammonium compounds. The nature of the counterion is not critical at all for the practice of the present invention. The scope of this invention is not considered to be limited to any particular anion. By "amine precursors thereof" is meant the secondary or tertiary amines corresponding to the above quaternary ammonium compounds, said amines being substantially protonated in the present compositions due in part to the pH values. Additional fabric softening materials can be used in addition to the cationic fabric softener. These may be selected from nonionic, amphoteric or anionic fabric softening materials. The description of said materials can be found in E.U. 4,327,133; E.U. 4,421, 792; E.U. 4,426,299; E.U. 4,460,485; E.U. 3,644,203, E.U. 4,661, 269; E.U. 4,439,335; E.U. 3,861,870; E.U. 4,308,151; E.U. 3,886,075; E.U. 4,233,164; E.U.4,401, 578; E.U. 3,974,076; E.U. 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 (eg,> 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 sorbitol. 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 1,5-sorbitan esters. Preferred herein are glycerol and polyglycerol esters, especially mono- and / or glycerol, diglycerol, triglycerol and polyglycerol 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. "Glycerol esters" also include polyglycerol esters, for example, 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. Additional fabric softening components suitable for use herein are softening clays, such as those of low ion exchange capacity described in EP-A-0, 150,531. For prior fabric softening agents, especially biodegradable fabric softening agents, the pH of the compositions herein is an essential parameter of the present invention. In fact, it has an influence on the stability of the quaternary ammonium compounds or amine precursors, especially under conditions of prolonged storage. The pH, as defined in the present context, is measured in the concentrated compositions at 20 ° C. For optimum hydrolytic stability of these compositions, the concentrated pH, measured under the aforementioned conditions, should be in the range of 2.0 to 4.5. Preferably, when the liquid fabric softening compositions of the invention are in concentrated form, the pH of the concentrated composition is in the range of 2.0 to 3.5. The pH of these compositions 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-C5), and alkylsulfonic acids. Suitable inorganic acids include HCl, H2SO4, HNO3 and H3PO4. Suitable organic acids include formic, acetic, citric, methylsulfonic and ethylsulphonic acids. The acids that are preferred with citric, hydrochloric, phosphoric, formic, methylsulphonic and benzoic acids. The fabric softening compounds herein are present at levels of 1% to 80% of the compositions herein, depending on the performance of the composition that can be diluted with a preferred level of active agent from 5% to 15%, or can be concentrated with a preferred level of active agent from 15% to 50%, more preferably from 15% to 35% by weight of the composition. Fully formulated fabric softening compositions preferably contain, in addition to the components described above, one or more of the following ingredients.
Enzymes The composition herein may optionally employ one or more enzymes such as lipases, proteases, cellulase, amylases and peroxidases. An enzyme that is preferred for use herein is a cellulase enzyme. In fact, this type of enzyme will also provide a color care benefit to the treated fabric. Cellulases that can be used herein include both bacterial and fungal types, preferably having an optimum pH of between 5 and 9.5. The patent of E.U. A. 4,435,307, Barbesgoard et al., March 6, 1984, describes suitable fungal cellulases of Humicola insolens or of the DSM 1800 strain of Humicola or a cellulase-producing fungus 212 belonging to the genus Aeromonas. and a cellulase extracted from the hepatopancreas of a marine mollusk, Dolabella Auricular Solander. Suitable cellulases are also described in GB-A-2,075,028; GB-A-2,095,275 and DE-OS-2,247,832. They are especially useful
CAREZYMER and CELLUZYMER (Novo). 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 up to about 5 mg by weight, very typically 0.01 mg to 3 mg, of active enzyme per gram of the composition. In other words, the compositions herein will typically comprise from 0.001% to 5%, preferably 0.01% -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 enzymes at a level equivalent to an activity of about 0.5 to 1000 CEVU / gram of composition. The cellulase enzyme preparations used for the purpose of formulating the compositions of the 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.
The concentrated compositions of the present invention may require organic or inorganic concentrating aids to obtain even higher concentrations and / or to meet more stringent stability standards depending on the other ingredients. The surfactant concentration aids are typically selected from the individual long chain alkyl cationic surfactants, nonionic surfactants, amine oxides, fatty acids and mixtures thereof, typically used at a level of 0 to 15% the composition. Inorganic viscosity control agents that can also act as or enhance the effect of surfactant concentration aids include water-soluble ionizable salts which can also be optionally incorporated into the compositions of the present invention. A wide variety of ionizable salts can be used. Examples of suitable salts are the halides of group IA and HA of metals of the periodic table of the elements, for example, calcium chloride, magnesium chloride, sodium chloride, potassium bromide and lithium chloride. Ionizable salts are particularly useful during the process of mixing the ingredients to make the compositions herein, and then to obtain the desired viscosity. The amount of ionizable salts used depends on the amount of active ingredients used in the compositions, and can be adjusted according to the wishes of the formulator. Typical salt levels used to control the viscosity of the composition are from 20 to 20,000 parts per million (ppm), preferably from 20 to 11,000 ppm, by weight of the composition. The alkylene polyammonium salts can be incorporated into the composition to give viscosity control in addition to or in place of the above water-soluble water-soluble salts. further, these agents can act as scavengers, forming ion pairs with the anionic detergent that comes from the main wash, in the rinse and on the fabrics, and can improve the yield of softness. These agents can stabilize the viscosity on a broader scale of temperatures, especially at low temperatures, compared to inorganic electrolytes. Specific examples of alkylene polyammonium salts include l-lysine monohydrochloride and 1,5-diammonium 2-methylpentandichlorohydrate. Another optional but preferred ingredient is a liquid vehicle. The liquid carrier employed in the present compositions is preferably at least mainly 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%, most preferably at least 60% by weight of the vehicle. Mixtures of water and low molecular weight organic solvent, for example, <200, for example lower alcohol such as ethanol, propanol, isopropanol or butanol are useful as the liquid carrier. Low molecular weight alcohols include monohydric, dihydric (glycol, etc.), trihydric (glycerol, etc.) alcohol and higher polyhydric alcohols (polyols).
Other optional ingredients are dirt-releasing polymers, bactericides, colorants, perfumes, preservatives, optical brighteners, anti-ionization agents, anti-foam agents and the like. Various other optional auxiliary ingredients can also be used to provide fully formulated detergent compositions. The following ingredients are described for the convenience of the formulator, but are not intended to be limiting of the invention.
Detersive Surfactants Non-limiting examples of other surfactants useful herein typically at levels of about 1% to about 55% by weight, include the conventional C 1 -C-C? Alkylbenzene sulphonates ("LAS") and C 10 -C 20 alkyl sulfonates. primary branched and random chain ("AS"), secondary alkyl sulfates (2,3) of C-10-C18 of the formula CH3 (CH2) x (CHOS? 3-M +) CH3 and CH3 (CH2) and (CHOS) ? 3-M +) CH2CH3 where xy (y + 1) are integers of at least 7, preferably at least 9, and M is a cation that is solubilized in water, especially sodium, unsaturated sulfates such as oleyl sulfate, alkylalkoxy sulfates of C10-18 ("AExS", especially EO 1-7 ethoxysulfates), alkylalkoxycarboxylates of C-IQ-Cie (especially EO 1-5 ethoxycarboxylates), glycerol esters of C- | QC- | 8- the alkyl polyglucosides of C-10-18 and its corresponding sulphated polyglycosides, and alphasulfonated fatty acid esters of C- | 2- < | 8- if the alkyl ethoxylates of C12-18 ("AE"), which include so-called narrow-alkyl ethoxylates and C5-C12 alkylphenylalkysilates (especially ethoxylated and mixed ethoxy / propoxy), C12-C18 betaines and sulfobetaines ("sultaines") ), amine oxides of CI Q-CI S and the like, can also be included in the overall compositions. The N-alkyl polyhydroxy fatty acid amides can also be used. Typical examples include N-methylglucamides of C < i2-Ci8- See WO 9,206,154. Other surfactants derived from sugar include fatty acid amines of N-alkoxy polyhydroxy, such as N (3-methoxypropyl) glucamide from C < | o-C- | 8- The N-propyl to N-hexyl C12-C18 glucamides can be used for low foaming, conventional C10-C20 soaps can also be used. If high foaming is desired, branched-chain C10-C16 soaps can be used. Mixtures of anionic and nonionic surfactants are especially useful. Other useful conventional surfactants are listed in conventional texts.
Detergency Meters Detergency builders may optionally be included in the compositions herein to help control mineral hardness. Inorganic as well as inorganic builders can be used. Builders are typically used in fabric washing compositions to aid in the removal of particulate soils. The level of builder can vary greatly depending on the final use of the composition and the desired physical form. When present, the compositions commonly comprise at least 1% builder. Liquid formulations typically comprise from 5% to about 50%, very typically from about 5% to about 30% by weight, of the builder. The granulated formulations typically comprise from about 10% to about 80%, very typically from about 15% to about 50% by weight, of the builder. However, it is not intended to exclude lower or higher levels of detergency builder. Inorganic or phosphate-containing builders include, but are not limited to, the alkali metal, ammonium and alkanolammonium salts of polyphosphates (exemplified by crystalline polymeric tripolyphosphates, pyrophosphates, and meta-phosphates), phosphonates, phytic acid, silicates, carbonates (including bicarbonates and sesquicarbonates), sulfates and aluminosilicates. Nevertheless, non-phosphate detergent builders are required in some places. Importantly, the compositions herein work surprisingly well even in the presence of so-called "weak" builders (as compared to phosphates) such as citrate, or in the so-called "poor detergency" situation that can occur with zeolite or layered silicate builders. Examples of silicate builders are alkali metal silicates, particularly those having an Si? 2: Na2? Ratio. in the scale from 1.6: 1 to 3.2: 1 and the layered silicates, such as the layered sodium silicates described in the U.S.A. No. 4,664,839. NaSKS-6 is the trademark of a crystalline layered silicate marketed by Hoescht (commonly abbreviated herein as "SKS-6"). Unlike zeolite builders, the Na SKS-6 silicate builder does not contain aluminum. NaSKS-6 has the delta-Na2S2.25 morphology of stratified silicate. It can be prepared by methods such as those described in DE-A-3,417,649 and DE-A-3,742,043. SKS-6 is a highly preferred stratified silicate for use herein, but other layered silicates such as those having the general formula NaMSix? 2? +? .yH2? wherein M is sodium or hydrogen, x is a number from 1.9 to 4, preferably 2, and y is a number from 0 to 20, preferably 0. Other different stratified silicates from Hoechst include NaSKS-5, NaSKS-7 and NaSKS-11 , like the alpha, beta and gamma forms. As mentioned above, delta-Na 2 Si 2? 5 (NaSKS-6 form) is most preferred for use herein. Other layered silicates such as for example magnesium silicate, which can serve as a tightening agent in granular formulations, as a stabilizing agent for oxygen bleaches, and as a component of foam control systems may also be useful. Examples of carbonate builders are alkali earth and alkali metal carbonates such as those described in German Patent Application No. 2,231,001, published November 15, 1973. Aluminosilicate builders are useful in the present invention . The aluminosilicate builders of great importance in today's most widely sold heavy duty granular detergent compositions, and can also be an important detergency builder ingredient in liquid detergent formulations. The aluminosilicate builders include those with the empirical formula: Mz [(zAIO2) and]. XH2O where z and y are integers of at least 6, the molar ratio of zay is on the scale of 1.0 to 0.5, and x is an integer from 15 to 264, and M is an element of groups IA or HA, for example, Na, K, Mg or Ca with valence n. Useful aluminosilicate ion exchange materials are commercially available. These aluminosilicates may be of crystalline or amorphous structure and may be naturally occurring or synthetically derived aluminosilicates. A method for producing aluminosilicate ion exchange materials is described in US Patent 3,985,669, Krummel et al. Issued October 12, 1976. The preferred synthetic crystalline aluminosilicate ion exchange materials useful herein are available under the designations Zeolite A, Zeolite P (B), Zeolite MAP and Zeolite X. In an especially preferred embodiment, the ion exchange material of crystalline aluminosilicate has the formula: Na- | 2_ (AI02) 12 (S | 02) 12J H2? wherein x is from 20 to 30, especially 27. The material is known as Zeolite A. Dehydrated zeolites (x = 0-10) can also be used herein. Preferably, the aluminosilicate has a particle size of about 0.1-10 microns in diameter. Organic builders suitable for the purposes of the present invention include, but not restricted to, a wide variety of polycarboxylate compounds. As used herein, "polycarboxylates" refers to compounds having a plurality of carboxylate groups, preferably at least 3 carboxylates. Polycarboxylate builders can generally be added to the composition in acid form, but can also be added in the form of a neutralized salt. When used in the salt form, alkali metals such as sodium, potassium and lithium, or alkanolammonium salts are preferred. Included among the polycarboxylate builders are a variety of useful material categories. An important category of polycarboxylate builders comprises ether polycarboxylates, including oxydisuccinate, as described in Berg, U.S. 3,128,287, issued April 7, 1964, and Lamberti et al., Patent of E.U.A. 3,635,830, issued January 18, 1972. See also detergency builders of "TMS / TDS" of the U.S. patent. No. 4,663,071, issued to Bush et al. On May 5, 1987. Suitable ether polycarboxylates also include cyclic compounds, particularly alicyclic compounds, such as those described in U.S. Pat. 3,923,679; 3,835,163; 4,158,635; 4,120,874 and 4,102,903. Other useful builders include etherhydroxypolycarboxyiates, maleic anhydride copolymers with ethylene or vinyl methyl ether, 1,3,5-trihydroxybenzene-2,4,6-trisulfonic acid, and carboxymethyloxy-succinic acid, various alkali metal, ammonium and ammonium salts. substituted ammonium of polyacetic acids such as ethylenediaminetetraacetic acid and nitrilotriacetic acid, as well as polycarboxylates such as melific acid, succinic acid, oxydisuccinic acid, polymaleic acid, benzene-1, 3,5-tricarboxylic acid, carboxymethyloxysuccinic acid and soluble salts thereof. Citrate builders, for example, citric acid and soluble salts thereof (particularly sodium salt), are polycarboxylate builders of particular importance for heavy-duty liquid detergent formulations because of their availability from renewable resources and its biodegradability. The citrates can also be used in granular compositions, especially in combination with zeolite builders and / or layered silicate. Oxydisuccinates are also especially useful in said compositions and combinations. Also suitable in the detergent compositions of the present invention are the 3,3-dicarboxy-4-oxa-1,6-hexanedioates and the related compounds described in the US patent. No. 4,566,984, Bush, issued January 28, 1986. Useful succinic acid builders include the C5-C20 alkyl and alkenyl succinic acids and salts thereof. A particularly preferred compound of this type is dodecenylsuccinic acid. Specific examples of succinate builders include: laurylsuccinate, myristylsuccinate, palmitylsuccinate, 2-dodecenylsuccinate (preferred), 2-pentadecenylsuccinate, and the like. Lauryl succinates are the preferred builders of this group, and are described in EP 0,200,263. Other suitable polycarboxylates are described in the U.S.A. 4,144,226, and in the patent of E.U.A. 3,308,067. See also U.S. 3,723,322. Fatty acids, for example, C12-C monocarboxylic acids < (8) can also be incorporated into the compositions by themselves, or in combination with the aforementioned builders, especially citrate and / or succinate builders, to provide additional detergency builder activity. generally it will result in the decrease of foaming, which would be considered by the formulator.
In situations where phosphorus-based builders can be used, and especially in the bar formulations used for hand washing operations, various alkali metal phosphates such as the well-known sodium tripolyphosphates, sodium pyrophosphate, can be used. and sodium orthophosphate. Phosphonate builders such as ethan-1-hydroxy-1,1-diphosphonate and other known phosphonates can also be used (see, for example, U.S. Patents 3,159,581, 3,213,030, 3,422,021, 3,400,148 and 3,422,137).
Blanching Compounds - Blanching Agents and Blanching Activators The detergent compositions herein may optionally contain bleaching agents or bleaching compositions containing an agent and one or more bleach activators. When present, bleaching agents are typically at levels of from about 0.05% to about 30%, most preferably about 5% to about 20% of the detergent composition, especially for fabric washing. If present, the amount of bleach activators is typically from about 0.1% to about 60%, very typically from about 0.5% to about 40% of the bleaching composition containing the bleaching agent plus the bleach activator.
The bleaching agents used herein may be any of the bleaching agents useful for fabric cleaning detergent compositions that are now known or have become known. These include oxygenated bleaches, as well as other bleaching agents. Perborate bleaches, for example, sodium perborate (e.g., mono- or tetrahydrate) can be used herein. Another category of bleaching agent that can be used without restriction comprises percarboxylic acid bleaching agents and salts thereof. Suitable examples of this class of agents include magnesium monoperoxyphthalate hexahydrate, the magnesium salt of metachloroper-benzoic acid, 4-nonylamino-4-oxoperoxybutyric acid and hyperoxydedecanedioic acid. Said bleaching agents are described in the patent of E.U.A. 4,483,781, the U.S. Patent. 740,446, E P 0,133,354 and the Patent of E.U.A. 4,412,934. Highly preferred bleaching agents also include 6-nonylamino-6-oxoperoxycaproic acid as described in U.S. 4,634,551. Peroxygen bleaching agents can also be used. Suitable peroxygen bleach compounds include sodium carbonate peroxyhydrate and equivalent "perca rbonated" bleaches, sodium pyrophosphate peroxyhydrate, urea peroxyhydrate and sodium peroxide. Persulfate bleach can also be used (e.g., OXONE, commercially manufactured by DuPont).
A preferred percarbonate bleach comprises dry particles having an average particle size in the range of about 500 microns to about 1,000 microns, no more than about 10% by weight of said particles being larger than about 1,250 microns. Optionally, the percarbonate can be coated with silicate, borate or water-soluble surfactants. Percarbonate is available from various commercial supplies such as FMC, Solvay and Tokai Denka. Mixtures of bleaching agents can also be used. Peroxygen bleaching agents, perborates, percarbonates, etc., are preferably combined with bleach activators, which lead to in situ production in the aqueous solution (ie, during the washing process) of the peroxyacid corresponding to the activator bleaching. Various non-limiting examples of activators are described in the U.S. Patent. 4,9151,854 issued April 10, 1990 to Mao et al., And in the U.S. Patent. 4,412,934. Typical nonanoyloxybenzenesulfonate (NOBS), 3,5,5-trimethyl hexanoyl oxybenzenesulfonate (ISONOBS) and tetraacetylethylamine (TAED) activators, and mixtures thereof can also be used. See also E.U.A. 4,634,551 for other typical bleaches and activators, useful herein. Preferred amide-derived bleach activators are those of the formulas: R 1 N (R 5) C) O) R 2 C (O) LO R 1 C (O) N (R 5) R 2 C (O) L wherein R 4 is an alkyl group containing from about 6 to about 12 carbon atoms, R2 is an alkylene containing
1 to about 6 carbon atoms, R ^ is H or alkyl, aryl or alkaryl containing from about 1 to about 10 carbon atoms and L is any suitable residual group. A residual group is any group that is displaced from the bleach activator as a result of a nucleophilic attack on the bleach activator by the perhydrolysis anion. A preferred residual group is phenylisulfonate. Preferred examples of bleach activators of the above formulas ude (6-octanamido-caproyl) oxybenzenesulfonate, (6-nonanamidocaproyl) oxybenzenesulfonate and mixtures thereof as described in the patent of E.U.A. 4,634,551 which is rporated herein by reference. Another class of bleach activators udes activators of the benzoxazine type described by Hodge et al. In the U.S. Patent.
4,966,723. A highly preferred bleach activator of the benzoxazine type is:
Yet another class of preferred bleach activators udes acyl-lactam activators, especially acylcaprolactams and acylvalerolactams of the formulas:
wherein R > is H or an alkyl, aryl or alkaryl group containing from 1 to about 12 carbon atoms. Highly preferred lactam activators ude benzoylcaprolactam, octanoylcaprolactam, 3,5,5-trimethylhexanoylcaprolactam, nonanoylcaprolactam, decanoylcaprolactam, undecenoylcaprolactam, benzoylvalerolactam, octanoylvalerolactam, decanoylvalerolactam, undecenoylvalerolactam, nonanoylvalerolactam, 3,5,5-trimethylhexanoylvalerolactam and mixtures thereof. See also the U.S. Patent. No. 4,545,784 issued to Sanderson on October 8, 1985, rporated herein by reference, which describes acylcaprolactams, uding benzoylcaprolactam, adsorbed to sodium perborate. Bleaching agents other than oxygen bleaching agents are also known in the art and can be used herein. One type of non-oxygen bleaching agent of particular interest udes photoactivated bleaching agents such as sulfonated zand / or aluminum phthalocyanines. See U.S. Pat.
4,033,718 issued July 5, 1977 to Holcombe et al. If used, the detergent compositions typically should contain from about 0.025% to about 1.25% by weight of said bleaches, especially sulfonated zphthalocyanine. If desired, the bleaching compounds can be catalyzed by means of a manganese compound. Such compounds are well known in the art and ude, for example, the manganese-based catalysts described in the U.S.A. No. 5,246,621, patent of E.U.A. No. 5,244,594, patent of E.U.A. No. 5,114,606 and you are from pat. European pub. Nos. 549.271 A1, 549.272A1, 544.440A2 and 544.490A1. Preferred examples of these catalysts ude MnlV2 (u-O) 3 (1,4,7-trimethyl-1,4,7-triazacyclononane) 2- (PF6) 2, Mn '|| 2 (u-O) < (u-OAc) 2 (1, 4,7-trimethyl-1, 4,7-triazacyclononane) 2- (Cl 4) 2, MnlV 4 (uO) 6 (1,4,7-triazacyclononane) 4 - (Cl? 4) 2,
Mn '|| Mn? 4 (u-O)? (u-OAc) 2 (1, 4,7-trimethyl-1, 4,7-triazacyclononane) 2- (Cl 4) 3,
MnlV (i, 4,7-trimethyl-1, 4,7-triazacyclononane) - (OCH 3) 3 (PF 6) and mixtures thereof. Other metal-based catalysts ude those described in the U.S.A. 4,430,243 and patent of E.U.A. 5,114,611. The use of manganese with several complex ligands to improve bleaching is also reported in the following United States Patents: 4,728,455; 5,284,944; 5,246,612; 5,256,779; 5,280,117; 5,274,147; 5,153,161 and 5,227,084. As a practical matter, and not by way of limitation, the compositions and methods herein can be adjusted to provide in the order of at least one part per ten million of the active bleach catalyst species in the aqueous wash liquor, and will preferably provide about 0.1 ppm to about 700 ppm, most preferably about 1 ppm to about 500 ppm of the catalyst species in the wash liquor. Other preferred optional ingredients ude enzyme stabilizers, polymeric soil release agents, materials effective to inhibit the transfer of dyes from one fabric to another during the cleaning process (i.e., dye transfer inhibiting agents), polymeric dispersing agents, foam suppressors, optical brighteners or other brightening or bleaching agents, chelating agents, fabric softening clays, antistatic agents, other active ingredients, vehicles, hydrothopes, processing aids, dyes or pigments, solvents for liquid formulations, and solid fillers for stick compositions. The liquid detergent compositions may contain water and other solvents such as vehicles. The low molecular weight primary and secondary alcohols illustrated by methanol, ethanol, propanol and isopropanol are suitable. Monohydric alcohols are preferred for solubilizing surfactant, but polyols such as those containing from 2 to 6 carbon atoms and from 2 to 6 hydroxyl groups (eg, 1,3-propanediol, ethylene glycol, glycerin and the like) can also be used. , 2-propanediol). The compositions may contain from 5% to 90%, typically from 10% to 50% of said vehicles. The granular detergents can be prepared, for example, by spray drying (final product density of 520 g / l) or agglomeration (final product density greater than 600 g / l) of the base granule. The remaining dry ingredients can then be mixed in granular or powder form with the base granule, for example, in a rotating mixing cylinder, and the liquid ingredients (eg, nonionic surfactant and perfume) can be sprayed. The detergent compositions herein will preferably be formulated such that during use in aqueous cleaning operations, the wash water has a pH of between about 6.5 and about 11, preferably between about 7.5 and 10.5. Laundry products typically have a pH of 9-11. Techniques for controlling pH at recommended levels of use include the use of pH, alkali, acid regulators, etc., and are well known to those skilled in the art.
Method of Use A method is also provided herein for providing the delayed release of an active alcohol, comprising the step of contacting the material to be treated with an aqueous medium comprising a compound or composition of the invention.
By "material" is meant any surface on which the compound can be deposited. Typical examples of such material are fabrics, hard surfaces such as tableware, floors, bathrooms, toilets, kitchens and other surfaces that need the delayed release of an active alcohol. By "delayed release" is meant the release of the active component (e.g., perfume) for a longer period than by the use of the active agent (e.g., perfume) itself. In the composition examples, the abbreviated identifications for the components have the following meanings. DEQA: Di- (tallowyloxyethyl) dimethylammonium chloride DTDMAC: Disodbodimethylammonium Chloride Fatty Acid: Stearic acid of IV = 0 Electrolyte: Calcium chloride PEG: Polyethylene glycol 4000 Carezyme: Cellulite enzyme sold by NOVO Industries A / S LAS: Sodium linear alkybenzene sulfonate of C12 TAS: Sodium tallow alkyl sulfate XYAS: Sodium alkylsulphate of C- |? -Ci? XYEZ: A primary alcohol of Ci? -C? V predominant condensed with an average of Z moles of ethylene oxide Soap: Linear sodium alkylcarboxyiate derived from an 80/20 mixture of tallow and coconut oil. NaSKS-6: Crystalline layered silicate of the formula gamma- Na2Si2O5 MA / AA: Copolymer of 1: 4 maleic acid / acrylic acid with an average molecular weight of about 70,000
STPP: Anhydrous sodium tripolyphosphate Zeolite A: Hydrated sodium aluminosilicate of the formula Na- | 2 (A1? 2Si? 2) i2- 27H2O, which has a primary particle size in the range of 0.1 to 10 microns. Percarbonate: Anhydrous sodium percarbonate bleach with a sodium silicate coating (Si2 ratio: Na2? = 2: 1) at a weight ratio of percarbonate to sodium silicate of 39: 1 PB1: perborate whitener anhydrous sodium monohydrate of nominal formula NaB 2-H2 2 PB 4: Anhydrous sodium perborate tetrahydrate of nominal formula NaBO 2 3 H 2 O 2 H 2 O 2 Protease: Proteolytic enzyme sold under the trade name Savinase by Novo Industries AS with an activity of 13 KNPU / g Protease #: Proteolytic enzyme sold under the trade name Savinase by Novo Industries A / S with an activity of 4 KNPU / g Amylase: Amylolytic enzyme sold by Novo Industries A / S under the trade name Termamyl 60T with an activity of 300 KNU / g Lipase: Lipolytic enzyme sold by Novo Industries AS under the trade name Lipolase with an activity of 165 KLU / g CMC: Sodium carboxymethylcellulose DTPMP: Diethylenetriaminpenta (methylene phosphonic acid), commercial Organized by Monsanto under the trade name Dequest 2060 HEDP: Hydroxyethane-1, 1-diphosphonic acid SRA (Agents: Esters blocked at the ends with sulfo- Benzoyl liberators and with base structure of oxyethylene Dust) oxy and terephthaloyl Sulphate: Sodium sulphate anhydrous 1: 4,4'-bis (2-sulphotrisyl) biphenyl disodium brightener 1: 4,4, -bis (4-anilino-6-morpholino-1,3,5-triazin-2-yl) amino) stilben-2 brightener : Disodium 2'-disulfonate Photoactivated bleach: Sulfonated zinc phthalocyanine encapsulated in dextrin soluble polymer Silicon Anti-foams: Polydimethylsiloxane foam controller with a siloxane-oxyalkylene copolymer as a dispersing agent with a ratio of said foam controller to said dispersing agent from 10: 1 to 100: 1. Non-ionic: Ethoxylated / propoxylated mixed C-13-C15 fatty alcohol with an average degree of ethoxylation of 3.8 and an average degree of propoxylation of 4.5, sold under the trade name Plurafac LF404 by BASF Gmbh (low foaming). Metasilicate: Metasilicate of sodium (ratio S2: Na2? = 1.0) Silicate: Amorphous sodium silicate (ratio Si? 2: Na2? = 2.0) Carbonate: Anhydrous sodium carbonate 480N: Acrylic / methacrylic acid random copolymer 3: 7, average molecular weight of about 3500 Citrate: trisodium citrate dihydrate TAED: Tetraacetylethylenediamine Cationic precursor: Cationic precursor salt of trialkylammonium methylene dialkylcaprolactam peroxy-whitener of C5 with tosylate BzP: Dibenzoyl peroxide PMT: 1-phenyl-5-mercapto-1, 2,3,4-tetrazole Bismuth nitrate: Bismuth nitrate salt Paraffin: Paraffin oil marketed under the trade name Winog 70 by Wintershall BD / MA: Butadiene / maleic acid copolymer sold by Polysciences Inc. under the trade name do not. reference 07787 BSA: Amylolytic enzyme sold under the tradename LE 17 by Novo Industries A / S (enzyme activity of approximately 1%).
EXAMPLE OF SYNTHESIS I Preparation of dihydromyrcenyl bromoacetate
Bromoacetyl bromide (0.055 moles, 4.74 ml) was mixed with dichloromethane (80 ml), in a 150 ml conical flask, cooled in a cold water bath (10-15 ° C). To this solution, a mixture of dihydromyrcenol (0.055 mol, 9.6 ml) and pyridine (0.055 mol, 4.4 ml) in dichloromethane (20 ml) was added dropwise, with the total addition time being 15 to 30 minutes. The dropping funnel was adapted with a drying tube with calcium chloride. The reaction mixture was allowed to stir on the cold water bath for 5 hours. Then, the white precipitate of pyridinium chloride was filtered, and the reaction mixture was washed with distilled water (3x150 ml), dried over MgSO 4, and the solvent was removed under reduced pressure, producing a dark brown oil which is a mixture of dihydromyrcenyl bromoacetate (70 mol%) and dihydromyrcenol (30 mol%). Dihydromyrcenyl bromoacetate was separated as a colorless oil by distillation under reduced pressure (eg, 106 ° C / 3 mm Hg). The synthesis of the other alkyl bromoacetate, such as lilacyl bromoacetate, phenoxalyl bromoacetate or geranyl bromoacetate, was also carried out following the above synthesis example substituting the dihydromyrcenol for the required alcohol, i.e., linalool, phenoxyethanol or geraniol. For primary and tertiary alcohols, the yield under said conditions is generally greater than 95%.
EXAMPLE OF SYSTESIS II Preparation of linalyl chloroacetate
A) From chloroacetyl chloride Chloroacetyl chloride (0.04 mol, 3.2 ml) was mixed with dry toluene
(25 ml) in a 150 ml conical flask. To this solution was added dropwise a mixture of linalool (0.04 mol, 7.2 ml) and pyridine (0.04 mol, 3.2 ml) dry toluene (10 ml), with the total addition time being approximately 15 to 30 minutes. The dropping funnel was adapted with a drying tube with calcium chloride. The reaction mixture was allowed to stir at 50 ° C for 16 hours. Then, the white precipitate of pyridinium chloride was filtered, and the dark solution recovered was washed with a solution of 5% sodium acid carbonate (60 ml), distilled water (2x60 ml), dried over MGSO4, and the solvent it was removed under reduced pressure, producing a dark brown oil which was analyzed by 1H / 13C NMR and GC / MS, being a mixture of linalyl chloroacetate (75% molar) and linalool (25% molar). The linalyl chloroacetate is separated as a colorless oil by distillation under reduced pressure (eg, 104 ° C / 2 mm Hg).
B) From chloroacetic anhydride The above experiment was repeated, except that croroacetic anhydride (6.83 g, 0.04 mol) was used in place of chloroacetyl chloride. The solvent used was dichloromethane, rather than toluene. The reaction conditions were 2 hours 30 minutes at room temperature, and the reaction yielded a slightly brown oil which is approximately 95% pure linalyl chloroacetate. This can be further purified by distillation under reduced pressure as indicated above.
EXAMPLE OF SYNTHESIS lll Preparation of PEÍ 1800 E0.5
The ethoxylation is carried out in a stirred stainless steel autoclave of 7.57 I equipped for measurement and temperature control, pressure measurement, vacuum and inert gas purging, sampling, and for the introduction of ethylene oxide as liquid. A cylinder of 9.08 kg net of ethylene oxide (ARC) is used to release ethylene oxide as a liquid by means of a pump to the autoclave, with the cylinder placed on a scale, so that the change in weight of the cylinder could be monitored. A 750 g portion of polyethylenimine (PEI) (Nippon Shokubai, Epomin SP-018 having an average molecular weight of 1800 equaling about 0.417 moles of polymer and 17.4 moles of nitrogen functions) is added to the autoclave. The autoclave is then sealed and purged with air (applying vacuum to minus 28 mm of mercury, followed by pressurization with nitrogen up to 17,575 kg / cm2, and then ventilating at atmospheric pressure). The contents of the autoclave are heated to 130 ° C while vacuum is applied. After about one hour, the autoclave is charged with nitrogen to approximately 17,575 kg / cm 2 while the autoclave is cooled to approximately 105 ° C. More and more ethylene oxide is then added to the autoclave over time, while carefully monitoring the pressure, temperature and flow velocity of the ethylene oxide in the autoclave. The ethylene oxide pump is turned off, and cooling is applied to limit any temperature increase that results from any reaction exotherm. The temperature is maintained between 100 ° C and 110 ° C, while the total pressure is allowed to increase gradually during the course of the reaction. After a total of 375 g of ethylene oxide have been autoclaved (almost equivalent to half a mole of ethylene oxide per mole of PEI nitrogen function), the temperature is increased to 110 ° C, and The autoclave is left to stir for another hour. At this point, vacuum is applied to remove any unreacted residual ethylene oxide. The reaction mixture is then deodorized by passing it through approximately 2831 I of inert gas (argon or nitrogen) through a gas dispersion frit and through the reaction mixture while stirring and heating the mixture to 130 °. C. The final reaction product is cooled slightly and collected in glass vessels purged with nitrogen. The same procedure applied for PEI 1800 E0.5 can be used, but using another PEI such as PEI 1200 or PEI 600.
EXAMPLE OF SYNTHESIS IV Preparation of PEI 600 In 2s
The ethoxylation is carried out in a stirred stainless steel autoclave of 7.57 I equipped for measurement and temperature control, pressure measurement, vacuum and inert gas purging, sampling, and for the introduction of ethylene oxide as liquid. A cylinder of 9.08 kg net of ethylene oxide (ARC) is used to release ethylene oxide as a liquid by means of a pump to the autoclave, with the cylinder placed on a scale, so that the change in weight of the cylinder could be monitored. A 750 g portion of polyethylenimine (PEI) (having an average molecular weight of 600 equaling to about 1.25 moles of polymer and 17.4 moles of nitrogen functions) is added to the autoclave. The autoclave is then sealed and purged with air (applying vacuum to minus 28 mm of mercury, followed by pressurization with nitrogen to 17,575 kg / cm2, and then ventilating at atmospheric pressure). The contents of the autoclave are heated to 130 ° C while vacuum is applied. After about one hour, the autoclave is charged with nitrogen to approximately 17,575 kg / cm 2 while the autoclave is cooled to approximately 105 ° C. More and more ethylene oxide is then added to the autoclave over time, while carefully monitoring the pressure, temperature and flow velocity of the ethylene oxide in the autoclave. The ethylene oxide pump is turned off, and cooling is applied to limit any temperature increase that results from any reaction exotherm. The temperature is maintained between 100 ° C and 110 ° C, while the total pressure is allowed to increase gradually during the course of the reaction. After a total of 187.5 g of ethylene oxide have been autoclaved (almost equivalent to a quarter of a mole of ethylene oxide per mole of PEI nitrogen function), the temperature is increased to 110 ° C, and The autoclave is left to stir for another hour. At this point, vacuum is applied to remove any unreacted residual ethylene oxide. The reaction mixture is then deodorized by passing it through approximately 2831 I of inert gas (argon or nitrogen) through a gas dispersion frit and through the reaction mixture while stirring and heating the mixture to 130 °. C. The final reaction product is cooled slightly and collected in glass vessels purged with nitrogen.
EXAMPLE OF SYNTHESIS V Preparation of polyglycine dihydromircenylester based on PEI 1200
Polyethyleneimine PM 1200 (highly branched) commercially available from Polyscience (54.5 g, 1.3 moles of repeating units) is stirred in hot ethyl acetate (500 ml), and until it is completely dissolved, anhydrous sodium carbonate (70 g) is then added. g, 0.65 moles), followed by dihydromyrcenyl bromoacetate (90.1 g, 0.325 moles). The reaction mixture is stirred at 50 to 60 ° C for 14 hours, after which an NMR test shows that the reaction seems to be over. The sodium carbonate is filtered, and the ethyl acetate is then removed under vacuum. Diethyl ether (200 ml) is then added, and the reaction mixture is stored at 4 ° C for a few hours before it is filtered. Removal of the diethyl ether under vacuum produces the dihydromyrcenyl ester of polyglycine as a dark yellow gum (55.5 g). The same results were obtained where a polyethyleneimine PM 1800 or 600 was used, instead of polyethyleneimine PM 1200. Partially quaternized polyglycine dihydromircenyl ester can also be prepared using a partially quaternized polyethylenimine. Methods for preparing said partially quaternized polyethyleneimine are known in the art, and are typically carried out using polyethyleneimine PM 1200 with an excess of alkylating agent such as bromomethyl, chloromethyl or methyl tosylate for at least two days. Other active alcohol polyglycine esters are also obtained by replacing the dihydromyrcenyl bromoacetate with the corresponding bromoacetate of the active alcohol such as linalyl bromoacetate, phenoxanyl bromoacetate or geranyl bromoacetate.
EXAMPLE OF SYNTHESIS VI PEI hydroxyethylated / mixed methylcarbonyloxy-lanylated layered
Dissolve partially hydroxyethylated PEI PM 1800 E0.5 (9.68 g) in 100 ml of hot chloroform before adding anhydrous sodium carbonate (6.36 g, 0.06 mol) and geranyl bromoacetate (8.26 g, 0.03 mol). The mixture is stirred at 50 ° C for 1 hour, and then at room temperature for another 3 hours, after which sodium carbonate is removed by filtration. The filtrate is concentrated under vacuum, and the brown gum obtained is allowed to cool before adding another amount of diethyl ether (100 ml). To remove all unreacted geranyl bromoacetate, the gum is crushed with the ether until everything has been transformed into a fine powder. The mixture is then allowed to stir at room temperature for 1 hour, after which the fine powder is removed by filtration, dried thoroughly under vacuum in a desiccator before being finely milled, yielding 14.1 g of hydroxyethylated PEI / methylcarbonyloxygeranyl- mixed alkylate as a fine light brown powder, which was characterized by 1 H NMR (CDCl 3). The same results were obtained where polyethyleneimine (PM 1800 or 600) E0.5 was used instead of polyethyleneimine (PM 1200) E05. Other polyglycine esters of active alcohols are also obtained by replacing the geranyl bromoacetate with the corresponding bromoacetate of the active alcohol such as linalyl bromoacetate, phenoxanyl bromoacetate or dihydromyrcenyl bromoacetate.
EXAMPLE OF SYNTHESIS Vil PEÍ hydroxyethylated / mixed methylcarbonyloxy-eryloalkylated
Partially hydroxyethylated PEI PM 600, E0.25 obtained in the synthesis example IV (10.8 g, equaling to approximately 0.14 moles of polymer and 0.2 moles of nitrogen, a quarter of which has been hydroxyethylated) in 120 ml of ethyl acetate is mixed. warm before adding geranyl bromoacetate (13.76 g, 0.05 moles). The mixture is stirred at 50 ° C for 24 hours, after which the solution is concentrated under vacuum, and the gum obtained is allowed to cool before adding another amount of diethyl ether (150 ml). To remove all unreacted geranyl bromoacetate, the gum is crushed with the ether until everything has been transformed into a fine powder. The mixture is then allowed to stir at room temperature for 1 hour, after which the fine powder is removed by filtration, dried completely under vacuum in a desiccator before being finely milled, yielding 19.5 g of hydroxyethylated PEI / mixed methyl-carbonyloxygenated lime as a fine light brown powder, which was characterized by 1 H NMR (CDCl 3).
EXAMPLE OF SYNTHESIS VIII Preparation of polyglycine linalyl ester based on PEI 600
Polyethyleneimine PM 600 (highly branched) (7.5 g, about 0.2 mole repeat unit) commercially available from Polyscience in hot ethyl acetate (200 ml) is stirred, and until it is completely dissolved anhydrous sodium carbonate is then added.
(10.6 g, 0.1 mol), followed by linalyl chloroacetate (11.53 g, 0.05 mol).
The reaction mixture is stirred at 50 to 60 ° C for 100 hours, after which an NMR test shows that the reaction appears to be over. The sodium carbonate is filtered, and the ethyl acetate is then removed under vacuum. Petroleum ether is then added at 40-60 ° C (200 ml), and the reaction mixture is stored at 4 ° C for a few hours before it is filtered. Removal of the petroleum ether from 40 to 60 ° C under vacuum produces the polyglycine linallyl ester as a dark yellow gum (13.4g).
EXAMPLE OF SYNTHESIS IX Preparation of polypyridinium betaine esters
To a suspension of poly (4-vinylpyridine) (10.51 g, 0.1 moles of repeating units) commercially available from Aldrich in hot acetone, geranyl bromoacetate (13.76 g, 0.05 moles) is added. Then, the mixture is refluxed for 24 hours, after which the hot solution is filtered. The recovered solid is then stirred in diethyl ether (100 ml) for 10 minutes, filtered again, washed with diethyl ether, and dried under vacuum in a desiccator, yielding a poly (4-vinylpyridine). { poly [4-vinylpyridine / geranyloxycarbonylmethyl (4-vinipyridinium].] partially alkylated bromide, as a fine white powder (21.2 g) The different phases of acetone and ether contain any unreacted geranyl bromoacetate The invention is illustrated in the following non-limiting examples, in which all percentages are on an active weight basis, unless otherwise indicated.
EXAMPLE 1
The following fabric softening compositions are in accordance with the present invention.
(*) Compound of polymeric ester obtained in any of the synthesis examples V to IX.
EXAMPLE 2
The following surface cleaning compositions G to L are in accordance with the present invention.
(*) Compound of polymeric ester obtained in any of the synthesis examples V to IX. The processing of the compositions G and H was carried out by adding all the materials and mixing them with the polymeric compound of the invention. The processing of the composition I was carried out by adding all the components to a premix of the polymeric compound of the invention and perfume, followed by the addition of the remaining water.
Alternatively, all the materials, except the polymeric compound of the invention and perfume, were mixed, followed by the addition of said polymeric compound, and heating at 70 ° C for a short period, and the mixture is then allowed to cool to room temperature (20). ° C). Once the mixture was cooled to room temperature, the perfume component was added with stirring.
EXAMPLE 3
The following dishwasher compositions were prepared according to the invention.
(*) Compound of polymeric ester obtained in any of the synthesis examples V to IX.
EXAMPLE 4
The following laundry compositions according to the invention were prepared.
(*) Compound of polymeric ester obtained in any of the examples of
synthesis V to IX.
Claims (22)
- NOVELTY OF THE INVENTION CLAIMS 1- A polymer that contains at least one nitrogen atom, characterized in that at least one of the nitrogen atoms is attached to an ester group of formula: I [C] C OR I n3 wherein each R'-i, R'2 is independently selected from the group consisting of hydrogen, hydroxyl, alkyl group, alkylene group, aryl group, alkylaryl group, or any other chain containing at least one carbon atom, in where n3 is an integer that is on the scale of about 1 to about 3, and where R is an organic chain of an active alcohol. 2- The polymer according to claim 1, further characterized in that each R'1 (R'2 is independently selected from the group consisting of hydrogen, alkyl group, aryl group, (CH2) m -COOH, - (CH2) m -COOR, - (CH2) m'-OH, - (CH2) m'-O (O) CR ', wherein each m, independently, is an integer of value 0, 1 or 2, and each m', independently , is an integer of value 1, 2 or 3. The polymer according to any of claims 1 or 2, further characterized in that said polymer has a molecular weight less than about 100,000 4. The polymer according to the claim 3, further characterized in that said polymer has a molecular weight between about 300 and about 100,000 5. The polymer according to claim 3, further characterized in that said polymer has a molecular weight between about 500 and about 5,000. polymer according to claim 1, characterized by emás because said polymer is an amino functional polymer selected from the group consisting of polyamines, polyvinylpyridines, copolymers of poly (vinylpyrrolidone / vinylmidazole), polymers having rings of pyrolidine, polyvinylimidazoles, chitosans, and mixtures thereof, preferably polyamine polymers. 7- The polymer according to claim 6, further characterized in that said polyamine is selected from (a) linear or non-cyclic polyamines having a base structure of the formula: H [H2N - R '] n + 1 [N - R'] m [N - R '] p NH; b) cyclic polyamines having a base structure of the formula: H R ' [H2N - R '] n-k +? [N - R '] m [N - R'] [N - R '] - NH2 c) polyamines having a base structure of the formula: NH ; and mixtures thereof; wherein R 'is C2-C8alkylene, alkylene substituted with C3-C8alkyl, and mixtures thereof; preferably R 'is ethylene, 1,2-propylene, 1,3-propylene, and mixtures thereof, more preferably ethylene; wherein m is from about 2 to about 700; n is from 0 to about 350; k is less than n or equal to it; and is from about 5 to about 10,000, preferably from about 10 to about 5,000, more preferably from about 20 to about 5,000. 8- The polymer according to claim 7, further characterized in that said polyamine is a linear or non-cyclic polyamine. 9. The polymer according to claim 8, further characterized in that said polyamine is a polyethyleneimine polymer. 10- The polymer according to claim 9, further characterized in that said polyethyleneimine is a branched polyethyleneimine partially modified with - (R 1 O) xB; wherein R1 is selected from the group consisting of C2-C6 alkylene, alkylene substituted with C3-C6 alkyl, and mixtures thereof; B is selected from the group consisting of hydrogen, C6 alkyl, - (CH2) qSO3M, - (CH2) pCO2M, (CH2) q (CHSO3M) CH2SO3M, - (CH2) q- (CHSO2M) CH2S? 3M, - (CH2) pPO3M, -PO3M, and mixtures thereof; M is hydrogen or a water-soluble cation in sufficient quantity to satisfy the charge balance; q has a value from 0 to about 6; and x is from about 1 to about 100. 11- The polymer according to claim 10, further characterized in that R1 is ethylene and B is hydrogen. 12- The polymer according to claim 1, further characterized in that said group R is the organic chain of a perfume alcohol. 13. The polymer according to claim 12, further characterized in that said group R is the organic chain of a perfume alcohol, said alcohol being selected from 2-phenoxyethanol, phenyl ethyl alcohol, geraniol, citronellol, 3-methyl-5- phenyl-1-pentanol, 2,4-dimethyl-3-cyclohexene-1-methanol, linalool, tetrahydrolinalool, 1,2-dihydromyrcenol, hydroxycitronol, farnesol, menthol, eugenol, vanillin, cis-3-hexenol, terpineol, and mixtures thereof, preferably selected from geraniol, citronellol, linalool and dihydromyrcenol. 14- A composition that incorporates a polymer according to claim 1, characterized in that said composition is a cleaning or laundry composition. 15- The composition according to claim 14, further characterized in that said polymer is incorporated at a level of about 0.01% to about 10% by weight of the composition. 16- The composition according to claim 15, further characterized in that said polymer is incorporated at a level of about 0.05% to about 5% by weight of the composition. 17- The composition according to claim 15, further characterized in that said polymer is incorporated at a level of about 0.1% to about 2% by weight of the composition. 18- The composition according to claim 14, further characterized in that said composition is selected from the group consisting of a fabric softening composition, a detergent composition and a hard surface cleaning composition. 19. The composition according to claim 18, further characterized in that said composition further comprises an enzyme. 20- The composition according to claim 19, further characterized in that said enzyme is a cellulase. 21- A method for providing the delayed release of an active alcohol, characterized in that it comprises the step of contacting materials that will be treated with an aqueous medium comprising a compound or composition thereof, said compound containing at least one nitrogen atom , wherein at least one of the nitrogen atoms is attached to an ester group of the formula: R'-, I [C] ~ ^ C OR I I '2 O wherein each R'i, R'2, independently, is selected from the group consisting of hydrogen, hydroxyl, alkyl group, alkylene group, aryl group, alkylaryl group, or any other chain containing at least one carbon atom, in where n3 is an integer that is on the scale of about 1 to about 3, and where R is an organic chain of an active alcohol. 22. A process for preparing a polymeric ester compound containing at least one nitrogen atom, wherein at least one of the nitrogen atoms is attached to an ester group of the formula: wherein each R'-i, R'2, independently, is selected from the group consisting of hydrogen, hydroxyl, alkyl group, alkylene group, ary group, alkylaryl group, or any other chain containing at least one carbon atom , wherein n3 is an integer that is on the scale of about 1 to about 3, and wherein R is an organic chain of an active alcohol, said polymer being an amino-functional polymer, by reacting a polyamino-functional polymer with bromoacetate and / or chloroacetate of an active alcohol in the presence of a non-hydroxylated solvent.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP96306834.1 | 1996-09-19 | ||
EP97303352 | 1997-05-16 |
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MXPA99002627A true MXPA99002627A (en) | 1999-09-20 |
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