CA2549571A1 - Modified alkoxylated polyol compounds - Google Patents
Modified alkoxylated polyol compounds Download PDFInfo
- Publication number
- CA2549571A1 CA2549571A1 CA002549571A CA2549571A CA2549571A1 CA 2549571 A1 CA2549571 A1 CA 2549571A1 CA 002549571 A CA002549571 A CA 002549571A CA 2549571 A CA2549571 A CA 2549571A CA 2549571 A1 CA2549571 A1 CA 2549571A1
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy moieties
- capping unit
- compound
- anionic
- alkoxy moiety
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims description 38
- 229920005628 alkoxylated polyol Polymers 0.000 title description 35
- 239000000203 mixture Substances 0.000 claims abstract description 133
- 238000004140 cleaning Methods 0.000 claims abstract description 99
- -1 polyol compound Chemical class 0.000 claims abstract description 70
- 125000000129 anionic group Chemical group 0.000 claims abstract description 53
- 229920005862 polyol Polymers 0.000 claims abstract description 46
- 150000001412 amines Chemical class 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 239000004094 surface-active agent Substances 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 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 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- 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 claims description 15
- 239000000600 sorbitol Substances 0.000 claims description 15
- 229920000768 polyamine Polymers 0.000 claims description 13
- 150000004985 diamines Chemical class 0.000 claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 5
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 5
- 229930006000 Sucrose Natural products 0.000 claims description 5
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 claims description 5
- 239000000845 maltitol Substances 0.000 claims description 5
- 235000010449 maltitol Nutrition 0.000 claims description 5
- 229940035436 maltitol Drugs 0.000 claims description 5
- 230000002829 reductive effect Effects 0.000 claims description 5
- 239000005720 sucrose Substances 0.000 claims description 5
- 235000000346 sugar Nutrition 0.000 claims description 5
- KFYRJJBUHYILSO-YFKPBYRVSA-N (2s)-2-amino-3-dimethylarsanylsulfanyl-3-methylbutanoic acid Chemical compound C[As](C)SC(C)(C)[C@@H](N)C(O)=O KFYRJJBUHYILSO-YFKPBYRVSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 4
- 229920001221 xylan Polymers 0.000 claims description 4
- 150000004823 xylans Chemical class 0.000 claims description 4
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 claims description 3
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 0.000 claims description 3
- 229920002774 Maltodextrin Polymers 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 claims description 3
- 239000003760 tallow Substances 0.000 claims description 3
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 claims description 3
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- FTNIPWXXIGNQQF-UHFFFAOYSA-N Maltopentose Chemical compound OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(OC3C(OC(OC4C(OC(O)C(O)C4O)CO)C(O)C3O)CO)C(O)C2O)CO)C(O)C1O FTNIPWXXIGNQQF-UHFFFAOYSA-N 0.000 claims description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 2
- 229920000223 polyglycerol Polymers 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 2
- 229940068984 polyvinyl alcohol Drugs 0.000 claims description 2
- 239000000811 xylitol Substances 0.000 claims description 2
- 235000010447 xylitol Nutrition 0.000 claims description 2
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 2
- 229960002675 xylitol Drugs 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 18
- 229920002873 Polyethylenimine Polymers 0.000 claims 1
- 150000002314 glycerols Chemical class 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 47
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 108090000790 Enzymes Proteins 0.000 description 17
- 102000004190 Enzymes Human genes 0.000 description 17
- 229940088598 enzyme Drugs 0.000 description 17
- 239000004744 fabric Substances 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000758 substrate Substances 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 150000003077 polyols Chemical class 0.000 description 12
- 239000011734 sodium Substances 0.000 description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 230000004048 modification Effects 0.000 description 9
- 238000012986 modification Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000003599 detergent Substances 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 7
- 239000003945 anionic surfactant Substances 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- 238000005956 quaternization reaction Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 238000005576 amination reaction Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000002736 nonionic surfactant Substances 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- 150000008051 alkyl sulfates Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004851 dishwashing Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000036961 partial effect Effects 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 108091005804 Peptidases Proteins 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000007844 bleaching agent Substances 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 238000005201 scrubbing Methods 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 3
- 102000035195 Peptidases Human genes 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229960003237 betaine Drugs 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- 239000002888 zwitterionic surfactant Substances 0.000 description 3
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 108010059892 Cellulase Proteins 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 description 2
- 229910000503 Na-aluminosilicate Inorganic materials 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 230000003625 amylolytic effect Effects 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000000882 contact lens solution Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 239000002979 fabric softener Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000011121 hardwood Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003752 hydrotrope Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 230000002366 lipolytic effect Effects 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229940051841 polyoxyethylene ether Drugs 0.000 description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000429 sodium aluminium silicate Substances 0.000 description 2
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- 230000019635 sulfation Effects 0.000 description 2
- 238000005670 sulfation reaction Methods 0.000 description 2
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- ZQTZVZDKVXKWKI-UHFFFAOYSA-N 1-hydroxypropane-1,2-disulfonic acid Chemical compound OS(=O)(=O)C(C)C(O)S(O)(=O)=O ZQTZVZDKVXKWKI-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- VZYDKJOUEPFKMW-UHFFFAOYSA-N 2,3-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(S(O)(=O)=O)=C1O VZYDKJOUEPFKMW-UHFFFAOYSA-N 0.000 description 1
- XRIBIDPMFSLGFS-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropan-1-ol Chemical compound CN(C)C(C)(C)CO XRIBIDPMFSLGFS-UHFFFAOYSA-N 0.000 description 1
- VDQWQTYEEJHNSB-UHFFFAOYSA-N 2-[2,3,4,5,6-pentakis(2-hydroxyethoxy)hexoxy]ethanol Chemical compound OCCOCC(OCCO)C(OCCO)C(OCCO)C(OCCO)COCCO VDQWQTYEEJHNSB-UHFFFAOYSA-N 0.000 description 1
- CJAZCKUGLFWINJ-UHFFFAOYSA-N 3,4-dihydroxybenzene-1,2-disulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C(S(O)(=O)=O)=C1O CJAZCKUGLFWINJ-UHFFFAOYSA-N 0.000 description 1
- SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 description 1
- OJZGCEDLMNSDNY-UHFFFAOYSA-N 3-[2,3,4,5,6-pentakis(3-hydroxypropoxy)hexoxy]propan-1-ol Chemical compound OCCCOCC(OCCCO)C(OCCCO)C(OCCCO)C(OCCCO)COCCCO OJZGCEDLMNSDNY-UHFFFAOYSA-N 0.000 description 1
- PVXPPJIGRGXGCY-TZLCEDOOSA-N 6-O-alpha-D-glucopyranosyl-D-fructofuranose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)C(O)(CO)O1 PVXPPJIGRGXGCY-TZLCEDOOSA-N 0.000 description 1
- USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 101000605014 Homo sapiens Putative L-type amino acid transporter 1-like protein MLAS Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000005913 Maltodextrin Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100038206 Putative L-type amino acid transporter 1-like protein MLAS Human genes 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 229940048053 acrylate Drugs 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 239000012871 anti-fungal composition Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- MVIOINXPSFUJEN-UHFFFAOYSA-N benzenesulfonic acid;hydrate Chemical compound O.OS(=O)(=O)C1=CC=CC=C1 MVIOINXPSFUJEN-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001461 cytolytic effect Effects 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229940035034 maltodextrin Drugs 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229940063557 methacrylate Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 108010020132 microbial serine proteinases Proteins 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000007777 multifunctional material Substances 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229940070721 polyacrylate Drugs 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940079842 sodium cumenesulfonate Drugs 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- QEKATQBVVAZOAY-UHFFFAOYSA-M sodium;4-propan-2-ylbenzenesulfonate Chemical compound [Na+].CC(C)C1=CC=C(S([O-])(=O)=O)C=C1 QEKATQBVVAZOAY-UHFFFAOYSA-M 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 108010075550 termamyl Proteins 0.000 description 1
- 150000004026 tertiary sulfonium compounds Chemical class 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/08—Polyoxyalkylene derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Dermatology (AREA)
- Genetics & Genomics (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Inorganic Chemistry (AREA)
- Molecular Biology (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
- Polyethers (AREA)
Abstract
A modified polyol compound having alkoxylation and having at least one anionic capping unit, uses of the modified polyol compound having alkoxylation and having at least one anionic capping unit and cleaning compositions comprising the same.
Description
Modified Alkoxylated Polyol Compounds FIELD OF THE INVENTION
This invention relates to modified alkoxylated polyol compounds, methods of making modified alkoxylated polyol compounds, and cleaning compositions comprising the same.
BACKGROUND OF THE INVENTION
Polyol compounds such as sugars like sucrose or maltitose are known as a sustainable and readily available raw material. Ethoxyates of maltitol is known, e.g., CAS
503446-80-8. This material has been widely disclosed as a surfactant for cosmetic and other personal care applications such as that discussed in JP 2003-096182. Other known ethoxylated polyols include: ethoxylated manitol (CAS 53047-O1-2), ethoxylated inostol (CAS 503446-79-5), ethoxylated sorbitol (CAS 53694-15-8). JP 10-081744 discusses the production of polyetherpolyols by adding alkylene oxides to saccharide in the presence of amine catalysts.
However, as "catalyst" implies, the amine catalysts do not become incorporated into the polyetherpolyol structure.
Also known are a series of amine terminated ethoxylates known in the trade as JEFFAMINES~ sold by Huntsman. These are mainly derived from polyethylene glycol and mixtures of polyethylene glycol and polypropylene glycol where the glycols are aminated directly with ammonia and a catalyst. These are called JEFFAMINE D~ and JEFFAMINE ED~
series. The most complex mixture of the JEFFAMINES~ series is the T series.
The JEFFAMINES~ are based on either trimethylolpropane or glycerine and thus have three ammonia terminated ethoxy/propoxy branches radiating from the glycerin or trimethylolpropane core.
Amination of polyols with ammonia and other amines is further exemplified in US
5,371,119, but uses modification of the polyol specifically via epichlorohydrin to form a polyol bis-halohydrin followed by reaction with ammonia or an amine to form repeating networks of amino polyols. This results in formation of a complex polymerized mixture containing multiple polyols linked randomly via the reactive halo hydrin. This complex mixture is not believed to be of value to formulators of cleaning compositions fox the purpose of providing cleaning benefits and is targeted towards forming emulsifiers.
Simple amination ofpolyols are described in WO 01/98388 A1 discussing simple aminated polyols, further reacted with aldehydes, in particular formaldehyde, to make complex polymeric networks. Included in these complex structures is the ability to have sulfide, carboxylate, alkyl esters, alkyl sulphonates, and alkyl phosphates as a functional unit of the complex structure.
This invention relates to modified alkoxylated polyol compounds, methods of making modified alkoxylated polyol compounds, and cleaning compositions comprising the same.
BACKGROUND OF THE INVENTION
Polyol compounds such as sugars like sucrose or maltitose are known as a sustainable and readily available raw material. Ethoxyates of maltitol is known, e.g., CAS
503446-80-8. This material has been widely disclosed as a surfactant for cosmetic and other personal care applications such as that discussed in JP 2003-096182. Other known ethoxylated polyols include: ethoxylated manitol (CAS 53047-O1-2), ethoxylated inostol (CAS 503446-79-5), ethoxylated sorbitol (CAS 53694-15-8). JP 10-081744 discusses the production of polyetherpolyols by adding alkylene oxides to saccharide in the presence of amine catalysts.
However, as "catalyst" implies, the amine catalysts do not become incorporated into the polyetherpolyol structure.
Also known are a series of amine terminated ethoxylates known in the trade as JEFFAMINES~ sold by Huntsman. These are mainly derived from polyethylene glycol and mixtures of polyethylene glycol and polypropylene glycol where the glycols are aminated directly with ammonia and a catalyst. These are called JEFFAMINE D~ and JEFFAMINE ED~
series. The most complex mixture of the JEFFAMINES~ series is the T series.
The JEFFAMINES~ are based on either trimethylolpropane or glycerine and thus have three ammonia terminated ethoxy/propoxy branches radiating from the glycerin or trimethylolpropane core.
Amination of polyols with ammonia and other amines is further exemplified in US
5,371,119, but uses modification of the polyol specifically via epichlorohydrin to form a polyol bis-halohydrin followed by reaction with ammonia or an amine to form repeating networks of amino polyols. This results in formation of a complex polymerized mixture containing multiple polyols linked randomly via the reactive halo hydrin. This complex mixture is not believed to be of value to formulators of cleaning compositions fox the purpose of providing cleaning benefits and is targeted towards forming emulsifiers.
Simple amination ofpolyols are described in WO 01/98388 A1 discussing simple aminated polyols, further reacted with aldehydes, in particular formaldehyde, to make complex polymeric networks. Included in these complex structures is the ability to have sulfide, carboxylate, alkyl esters, alkyl sulphonates, and alkyl phosphates as a functional unit of the complex structure.
However, the resulting complex polymeric networks is not believed to be of value to formulators of cleaning compositions for the purpose of providing cleaning benefits.
Additionally, it has not been taught to manipulate these materials in a controlled and specific manner.
Selective modification of sugar derived polyols to provide modified polyols where the star like structure is tuned to meet the needs of detergent formulators is highly desirable.
There also exists a need for materials that are relatively easy to manufacture from sustainable and readily available raw materials, which may be broadly tuned to address specific performance requirements. .
Stressed conditions also give the additional problem of having anionic surfactants such as linear alkylbenzene sulfonates or alkyl sulfates form larger order aggregates.
The aggregation of the anionic surfactant reduces the amount of the anionic surfactant available to clean.
There exists a need fox materials that are relatively easy to manufacture from sustainable and readily available raw materials, which may be tuned in a controlled and specific manner to address specific formulability and performance requirements. A multifunctional material that provides cleaning and gives increased surfactant availability by preventing formation of larger ordered aggregates of anionic surfactant with free hardness during use is desired.
Specific performance requirements include providing cleaning of hydrophobic stains (grease, oil) to hydrophilic stains (clay) associated with outdoor soils.
Other performance requirements include used in personal care compositions, such as contact lens solution, uses in adhesives, vulcanization of rubbers, use in polyurethane processes, use as dye additives, use as a dispersant in agricultural applications, use as dispersants for inks, asphalt dispersants, surfactant dissolution aides, in use surfactant solubilizers in presence of calcium and magnesium among other performance requirements.
Formulability of some of the current commercial polymers, which provide cleaning of outdoor soils, into granular and liquid laundry detergents, hard surface cleaners, dish cleaning compositions, personal care compositions as well as oil drilling compositions continues to challenge detergent formulators.
SUMMARY OF THE INVENTION
The present invention relates to compounds, processes, cleaning compositions, and methods of using said compounds and compositions characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties further comprise an anionic capping unit.
Additionally, it has not been taught to manipulate these materials in a controlled and specific manner.
Selective modification of sugar derived polyols to provide modified polyols where the star like structure is tuned to meet the needs of detergent formulators is highly desirable.
There also exists a need for materials that are relatively easy to manufacture from sustainable and readily available raw materials, which may be broadly tuned to address specific performance requirements. .
Stressed conditions also give the additional problem of having anionic surfactants such as linear alkylbenzene sulfonates or alkyl sulfates form larger order aggregates.
The aggregation of the anionic surfactant reduces the amount of the anionic surfactant available to clean.
There exists a need fox materials that are relatively easy to manufacture from sustainable and readily available raw materials, which may be tuned in a controlled and specific manner to address specific formulability and performance requirements. A multifunctional material that provides cleaning and gives increased surfactant availability by preventing formation of larger ordered aggregates of anionic surfactant with free hardness during use is desired.
Specific performance requirements include providing cleaning of hydrophobic stains (grease, oil) to hydrophilic stains (clay) associated with outdoor soils.
Other performance requirements include used in personal care compositions, such as contact lens solution, uses in adhesives, vulcanization of rubbers, use in polyurethane processes, use as dye additives, use as a dispersant in agricultural applications, use as dispersants for inks, asphalt dispersants, surfactant dissolution aides, in use surfactant solubilizers in presence of calcium and magnesium among other performance requirements.
Formulability of some of the current commercial polymers, which provide cleaning of outdoor soils, into granular and liquid laundry detergents, hard surface cleaners, dish cleaning compositions, personal care compositions as well as oil drilling compositions continues to challenge detergent formulators.
SUMMARY OF THE INVENTION
The present invention relates to compounds, processes, cleaning compositions, and methods of using said compounds and compositions characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties further comprise an anionic capping unit.
The present invention further relates compounds, processes, cleaning compositions, and methods of using said compounds and compositions characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties is replaced by and thus further comprises an anionic capping unit and at least one of the hydroxy moieties is substituted by an amine capping unit.
The present invention further relates compounds, processes, cleaning compositions, and methods of using said compounds and compositions characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties is replaced by and thus further comprises an anionic capping unit and at least one of the hydroxy moieties is substituted by a quaternary amine capping unit.
The present invention further relates compounds, processes, cleaning compositions, and methods of using said compounds and compositions characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties is replaced by and thus further comprises an anionic capping unit, at least one of the hydroxy moieties is substituted by an amine capping unit and at least one of the hydroxy moieties is substituted by a quaternary amine capping unit.
DETAILED DESCRIPTION OF THE INVENTION
There exists a need for materials that are relatively easy to manufacture from sustainable and readily available raw materials, which may be broadly tuned to address specific formidability and performance requirements.
Polyol compounds such as sugar based materials and polyethylene/polypropylene glycol materials axe sustainable and readily available raw materials that lend themselves to be broadly tuned to address specific formulability and performance requirements. As used herein "tune"
means having the ability to manipulate the chemical structure of the polyol compounds to achieve distinguishing chemical functionality. For example, an alkoxylated polyol compound modified by comprising an anionic capping unit is a tuned structure giving desired characteristics for specific formulability and performance requirements. Another example, an allcoxylated polyol compound modified by comprising an anionic capping unit and amine capping unit is a tuned structure giving desired characteristics. Another example is when an alkoxylated polyol compound is modified by comprising an anionic capping unit and a quaternary amine capping unit, is a tuned structure giving desired characteristics. Finally another example may contain both elements of the two examples, thus containing an anionic capping unit and an amine and quaternary amine capping unit.
The polyol compounds useful in the present invention comprises at least three hydroxy moieties, preferably more than three hydroxy moieties. Most preferably six or more hydroxy moieties. At least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy (E0), propoxy (PO), butoxy (BO) and mixtures thereof preferably ethoxy and propoxy moieties, more preferably ethoxy moieties. The average degree of alkoxylation is from about 1 to about 100, preferably from about 4 to about 60, more preferably from about 10 to about 40. Alkoxylation is preferably block alkoxylation.
The polyol compounds useful in the present invention further have at least one of the alkoxy moieties comprising at least one anionic capping unit. Further modifications or tuning of the compound may occur, but one anionic capping unit must be present in the compound of the present invention. One embodiment comprises more than one hydroxy moiety further comprising an alkoxy moiety having an anionic capping unit. For example formula (I):
O(EO)xH O(EO)XS03Na+
Na+
+Na 03 +Na 03Sx(OE)O O(EO)XS03Na+
formula (I) wherein x of formula (I) is from about 1 to about 100, or such as from about 10 to about 40.
Suitable anionic capping unit include sulfate, sulfosuccinate, succinate, maleate, phosphate, phthalate, sulfocarboxylate, sulfodicarboxylate, propanesultone, 1,2-disulfopropanol, sulfopropylamine, sulphonate, monocarboxylate, methylene carboxylate, ethylene carboxylate, carbonates, mellitic, pyromellitic, sulfophenol, sulfocatechol, disulfocatechol, tartrate, citrate, acrylate, methacrylate, poly acrylate, poly acrylate-maleate copolymer, and mixtures thereof.
Preferably the anionic capping units are sulfate, sulfosuccinate, succinate, maleate, sulfonate, methylene carboxylate and ethylene carboxylate.
Suitable polyol compounds for starting materials for use in the present invention include maltitol, sucrose, xylitol, glycerol, pentaerythitol, glucose, maltose, matotriose, maltodextrin, maltopentose, maltohexose, isomaltulose, sorbitol, poly vinyl alcohol, partially hydrolyzed polyvinylacetate, xylan reduced maltotriose, reduced maltodextrins, polyethylene glycol, polypropylene glycol, polyglycerol, diglycerol ether and mixtures thereof.
Good examples include the polyol compound being selected as sorbitol, maltitol, sucrose, xylan, polyethylene glycol, polypropylene glycol and mixtures thereof. Another group for the polyol compound is sorbitol, maltitol, sucrose, xylan, and mixtures thereof.
Tuning of the polyol compounds can be derived from one or more modifications, dependant upon the desired formidability and performance requirements. Tuning requires anionic modifications and can include incorporating a cationic or zwitterionic charge modifications to the polyol compounds.
In one embodiment of the present invention, at least one hydroxy moiety comprises an alkoxy moiety, wherein the alkoxy moiety further comprises at least one anionic capping unit.
In another embodiment of the present invention, at least one hydroxy moiety comprises an alkoxy moiety, wherein the alkoxy moiety further comprises more than one anionic capping unit, wherein at least one anionic capping unit, but less than all anionic capping units, is then selectively substituted by a amine capping unit. The amine capping unit is selected from a primary amine containing capping unit, a secondary amine containing capping unit, a tertiary amine containing capping unit, and mixtures thereof.
Suitable primary amines for the primary amine containing capping unit include monoamines, diamine, triamine, polyamines, and mixtures thereof. Suitable secondary amines for the secondary amine containing capping unit include monoamines, diamine, triamine, polyamines, and mixtures thereof. Suitable tertiary amines for the tertiary amine containing capping unit include monoamines, diamine, triamine, polyamines, and mixtures thereof.
Suitable monoamines, diamines, triamines or polyamines for use in the present invention include ammonia, methyl amine, dimethylamine, ethylene diamine, dimethylaminopropylamine, bis dimethylaminopropylamine (bis DMAPA), hexemethylene diamine, benzylamine, isoquinoline, ethylamine, diethylamine, dodecylamine, tallow triethylenediamine, mono substituted rnonoamine, monosubstituted diamine, monosubstituted podyamine, disubstituted monoamine, disubstiuted diamine, disubstituted polyamine, trisubstituted triamine, tri-substituted polyamine, multisubstituted polyamine comprising more than three substitutions provided at least one nitrogen contains a hydrogen, and mixtures thereof.
In another embodiment of the 'present invention, at least one of nitrogens in the amine capping unit is quaternized. As used herein "quaternized" means that the amine capping unit is given a positive charge through quaternization or protonization of the amine capping unit. For example, bis-DMAPA contains three nitrogens, only one of the nitrogens need be quaternized.
However, it is preferred to have all nitrogens quaternized on any given amine capping unit.
The tuning or modification may be combined depending upon the desired formulability and performance requirements. Non-limiting examples of modified polyol compounds of the present invention include:
+ +
(CHz)zN(CHs)z(CHz)sN(CH3)a ~3 formula (II)wherein x of formula (I) is from about 1 to about 100; and such as from about 10 to about 40.
+ +
+ + O(EOya(CHz)zN(CH3)z(CHz)~(CHs)3 + +
O (EO)~ 4(CH~ZN(CH3~(CI~)3N(CH3)3 _ ~ 8 Cl ~~h5s~3 N3+
5H O ~O(~hsS03'Na ~(EO), sS03'Na formula (III) ~'3S~.s(~E~'~~ r~ ~ ~ $ Cl + +
~~~~~15~U3 formula (IV) Process of Making The present invention also relates to a process fox making the compound of the present invention. The process for making the compound of the present invention comprises the optional step of alkoxylating a polyol compound comprising at least three hydroxy moieties such that the average degree of alkoxylation of at least one hydroxy moiety is between about 1 and about 100;
and such as from about 4 to about 60; further such as from about 10 to about 40; to form an alkoxylated polyol comprising at least one alkoxy moiety. Alternatively, an alkoxylated polyol, such as CAS 52625-13-5, a propoxylated sorbitol or sorbitol polyoxy ethylene ether available + +
~fECh, afCI-~~~~fGI~~N(CFi~?~
from Lipo Chemicals Inc., may be used as the starting material of the present invention. If the average degree of alkoxylation is not a desired level, an alkoxylation step may be used to achieve the desired degree of alkoxylation from about 1 to about 100, and such as from about 4 to about 60; further such as from about 10 to about 40. Next, the process comprises the step of reacting at least one alkoxy moiety of the compound with an anionic capping unit to form an anionic alkoxylated polyol, although more anionic capping units may be selected.
In one embodiment the process comprises another step of substituting at least one anionic capping unit of the anionic alkoxylated polyol with an amine capping unit to form an anionic aminated alkoxylated polyol. In this process only certain anionic capping units may be substituted such as sulfate, phosphate and carbonate. The process may further comprise the step of quaternizing at least one of the nitrogens in the amine capping of the anionic aminated alkoxylated polyol to form a zwitterionic alkoxylated polyol. Quaternization can be performed on any of the anionic aminated alkoxylated polyols. In one embodiment, the process comprises the step of alkoxylating some or most of the hydroxy moieties of the polyol such that the degree of alkoxylation is from about 1 to about 100; and such as from about 4 to about 60, further such as from about 10 to about 40; to form an alkoxylated polyol. The process further comprises the step of reacting the alkoxy moiety of the alkoxylated polyol with at least one anionic capping unit containing as least one of the following anionic groups; sulfate, phosphate and carbonate; to form an anionic alkoxylated polyol. The process may partially or completely react the alkoxy moiety of the alkoxylated polyol with an anionic capping unit. It is also understood that anionic capping units other than sulfate, phosphate or carbonate may also be present in the anionic alkoxylated polyol. Preferably all alkoxy moieties comprise an anionic capping unit.
Optionally, the process comprises the step of substituting the anionic capping unit with an amine capping unit selected from sulfate, phosphate and carbonate and mixtures thereof, to form an aminated anionic alkoxylated polyol (scheme I below). The substitution of the anionic capping units present with an amine capping unit may be partial or complete.
Preferably the subsitution of the anionic capping unit with the amine capping unit is partial forming an anionic aminated alkoxylated polyol.
Optionally, the process also comprises the process of providing an aminated alkoxylated polyol by direct amination of the alkoxylated polyol using catalytic amination (scheme II below) Optionally, the process may further comprise the step of quaternizing at least one of the nitrogens of the amine capping unit of the anionic aminated alkoxylated polyol forming a zwitterionic alkoxylated polyol. The quaternization of the amine capping unit of the anionic aminated alkoxylated polyol may be partial or complete. In one embodiment, the quaternization is partial. In another embodiment, the quaternization is complete. The quaternization of the nitrogens of the amine capping unit may be partial or complete, preferably complete. A
nonlimiting synthesis scheme is exemplified in Synthesis Scheme I and Synthesis Scheme II
below:
Synthesis Scheme I Anionic aminated alkoxylated polyol H(OE)x0 off off 6 times x EO o(EO),~H
OH O(EO)XH
STEP 1 H Base Catalyst H(oE)xo OH OH H(OE)x0 O(EO)xH
H(OE)x0 +Na 05S(OE)x0 p(EO)KS03Na+
p(~7hH
6 ClS03H o(EO)~SO,Na+
STEP 2 H(pE)x0 ~~)xH ~ +Na 03S(OE)X
CHZCIz Na035(OE~ EO SO Na H(OE)x0 O(HO)xH
+Na03S(OE)XO O(EO)~.S03Na+ 3 (CH3)2NH (CHy~NCHzCHZ(OE)x.~0 O(EO)nSO3Na+
STEP 3 +Na'03S(OE)n O(EO)xS03Na+ ~ O(EO)K_iCHZCHZN(CHy)z Na OgS(OE)x ~ Heatl Pressure ~
+Na03S(OE~ ~EO)xS03Na+ ' 3 OSO Na+ (Cf~~NCH2CH2(OE)x_~~O)"SD3Na+
(CI~)zNCHZCHz(OE~_i0 ~)%S~Na' (CHy)3NCH2CH2(OE~_~ O
EO)KSO~
3 (CH30)ZS02. k STEP 4 EO)x_~CHpCHyN(CH3)Z EO)x.~CHZCH2N(CH~)~
+Na-03S(OB)x ~ b,s(OE)xo (CH3)7NCH2CH2(OE~_i o(EO)xs~Na+ Heat/H20 (CHy)3+CHzCHa(OE~n a EO)xSOJ
The process rnay comprise optionally Step 1, Step 2, and optionally, Step 3 and 4. The step to providing the anionic aminated alkoxylated polyol via a neucleophilic substitution of sulfate moieties by an amine capping unit should be noted. This is a nonlimiting example as phosphate or carbonate groups may also be used for substitution by an amine capping unit.
Synthesis Scheme II:
H(OE~O EO
off OH 6 times x EO « )'~
OH O(EO)TI-I
STEP 1 H H(OE~p Base Catalyst OH OH H(OE~O O(EO),~H
H(OE~O p(~~H
NH3 HZNCH2CHz(OE~.iO p EO H
STEP 2 «HO~H > ( )x H(OE~O See US 5003107 (EO)x.,CH2cHZNH2 H(OE~
H(pE~p o(EO~H or US 23139289A1 by Huntsman for HZNCH2CHz(OE~_~~O)xH
procedure to reapply HZNCHzCHz(OE)x.ip O(EO)xH (CHs)aNCHZCHZ(pE)x.i0 O(EO)XH
+
O(EO)x_~CHZCHZNHZ 9 (CH30)ZSO2. O(EO)x_~CHZCHZN(CH3)3 STEP 3 H(OE~ ---~ H(OE~
HZNCHZCHZ(OE~_~ EO)xH base (pH3hNCHxCHz(OE)x_~ Ep)xH
+
+ 9 CH30S03Na (CH3)3NCHZCH2(OE~.iO p(EO)xH
+ +
O(EO)X_iCH2CHZN(CH3)3 Transsulfation (cH,),NCHzcHz(oEk_,o ~~xs~.
STEP 4 H(pE)x HZ~ EO)x,~CFizCH2N(CH~)3 (CH3)yNCHZCH2(OE~_~ Ep)xH -O~S(OE)x0 + Heat (CH~)~+CH2CHz(OE~_~ O(~)xSO;
+ 9 CH30S03Na Scheme II is distinguished from Scheme I in two areas; (1) direct substitution of the terminal hydroxy moieties is accomplished by catalytic oxidationlreduction using metal catalysts and hydrogen; (2) sulfation is carried out after amination and quatemization by transulfation as disclosed in LTS 6,452,035. A zwitterionic alkoxylated polyol of the same composition may be prepared by either Scheme I or Scheme II above. One of skill in the art will recognized that other amine capping units may be used, including but not limited to ammonia or dimethylaminopropylamine.
A specific description of the process of the present invention is described in more detail below.
Ethoxylation of Polyol Ethoxylation of the polyol, such as sorbitol, may be completed by any known technique, such as that described in EP 174436 A1 Propoxylation and butoxylation may also be completed by known techniques.
Add sorbitol (17.5g, 0.0962 mol) to an autoclave, purge the autoclave with nitrogen, heat sorbitol to 110-120°C; autoclave stirred and apply vacuum to about 20 mmHg.
Vacuum is continuously applied while the autoclave is cooled to about 110-120° C. while introducing 6.2g of a 25% sodium methoxide in methanol solution (0.0288 moles, to achieve a 5% catalyst loading based upon hydroxy moieties). The methanol from the methoxide solution is removed from the autoclave under vacuum. A device is used to monitor the power consumed by the agitator. The agitator power is monitored along with the temperature and pressure. Agitator power and temperature values gradually increase as methanol is removed from the autoclave and the viscosity of the mixture increases and stabilizes in about 1.5 hours indicating that most of the methanol has been removed. The mixture is further heated and agitated under vacuum for an additional 30 minutes.
Vacuum is removed and the autoclave is cooled to or kept at 110° C.
while it is being charged with nitrogen to 1725 kPa (250 psia) and then vented to ambient pressure. The autoclave is charged to 1380 kPa (200 psia) with nitrogen. Ethylene oxide is added to the autoclave incrementally while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate while maintaining the temperature between 110 and 120° C. and limiting any temperature increases due to reaction exotherm. After the addition of 483g of ethylene oxide (10.97 mol, resulting in a total of 19 moles of ethylene oxide per mol of OH), the temperature is increased to I20° C. and the mixture stirred for an additional 2 hours.
The reaction mixture is then collected into a 22 L three neck round bottomed flask purged with nitrogen. The strong alkali catalyst is neutralized by slow addition of 2.8g methanesulfonic acid (0.00288 moles) with heating (110° C.) and mechanical stirring.
The reaction mixture is then purged of residual ethylene oxide and deodorized by sparging an inert gas (argon or nitrogen) into the mixture through a gas dispersion frit while agitating and heating the mixture to 120° C. for 1 hour. The final reaction product, approximately SOOg, is cooled slightly, and poured into a glass container purged with nitrogen for storage.
Alternatively, polyol may be purchased with a degree of alkoxylation that is at or below that desired, such as CAS S262S-13-S, a propoxylated sorbitol or sorbitol polyoxy ethylene ether available from Lipo Chemicals Inc. Wherein the desired degree of alkoxylation is achieved by the processes known and/or described above.
Sulfation of Sorbitol EO,~d (Average of 19 EO moieties per hydroxy moiety) Weigh into a SOOmI Erlenmeyer flask Sorbitol El4 (299.7g, O.OS8 mol) and methylene chloride (300g) ("the solution") . Equip the flask with a magnetic stirring bar and stir until complete dissolution. Place the flask in an ice bath until the solution reaches about 10°C. Stir vigorous while slowing pouring chlorosulfonic acid (48.3g, 0.415 mol) over the period of about S
minutes to form a reaction solution. Stir the reaction solution in the ice bath for 1.5 hours.
Place a solution of sodium methoxide (197g of 2S% in methanol) in SOg of methylene chloride in a IL Erlenmeyer flask ("base solution") and chill in an ice bath until the temperature of the solution reaches about 10°C. Stir the base solution vigorous using a magnetic stirring bar.
Slowly pour the reaction solution into the base solution over a period of about 3 minutes. A mild exotherm should be observed. The resulting solution becomes milky as salts form. After addition is complete, measure the pH to be about 12. Add to this resulting solution about 100 ml of distilled water, and transfer the resulting emulsion to a 1L round bottom flask and use a rotary evaporator at 50°C to strip, in portions, to obtain a clear solution.
Transfer the clear solution to a Kulgelrohr apparatus. At 60°C and 133 Pa (lmm Hg) strip the solution to yield 366g of off white waxy solid, 90% active (10% salts).
Carbon NMR spectrum (500 MHz; pulse sequence: s2pul, solvent D20; relax. delay 0.300 sec, pulse 45.0; acq. time 1.090 sec) shows an absence of alcohol groups at about 60ppm and the emergence of a new peak at about 67ppm consistent with formation of the end group sulfate. Proton NMR spectrum (500 MHz or 300 MHz; pulse sequence: s2pul, solvent DzO;
relax. delay 1.000 sec, pulse 45.0; acq. time 2.345 sec) shows a new peak at about 4ppm which was integrated against the ethoxy group protons at about 3.Sppm and is consistent with the molecule having 6 end group sulfates.
Example 2: Amination of Sorbitol EO"n Hexasulfate Of Example 1 Weigh into a 200m1 glass liner sorbitol EO"4 hexasulfate (61.3g of 90% active, 0.0095 mol) and 3-(dimethylamino)propylamine ("DMAPA" 18.5g, 0.181 mol). Heat the liner in a rocking autoclave at 152 kPa (150 prig) under nitrogen until the temperature reaches 165°C and hold at 165°C for 2 hours. Cool to room temperature (20 - 25°C). Take the material up in 150 ml of methylene chloride and centrifuge to separate the salts. Transfer the supernatant to a SOOmI round bottom flask and strip the supernatant on a rotary evaporator at SO°C
until most (less than 5 mL) of the solvent is removed. Heat on a Kugelrohr apparatus at 120°C and 133 Pa (lmm Hg) for 30 minutes to remove excess amine to afford 47.8g of brown hard solid. Proton NMR
(500 MHz or 300 MHz; pulse sequence: s2pul, solvent D20; relax. delay 0.300 sec, pulse 45.0; acq. time 3.744 sec) indicated about 3 sulfates and about 2 DMAPA per molecule.
Examine 3: Quaternization of Amine Containing Sulfate Of Example 2 Dissolve an aminated Sorbitol EO,Ia in 100g of methylene chloride in a SOOmI
round bottom flask equipped with a magnestic stirring bar and chill in an ice bath until the temperature reaches 10°C. Adjust the solution to a pH 12 with sodium methoxide (25%
solution in methanol).
Add to the solution methyl iodide (lS.Og, 0.106mo1). Stopper the flask and stir the solution overnight (about 14 hours). Strip the solution on a Kugelrohr apparatus at 50°C and 133 Pa (lmm Hg) to afford 66g of tacky brown solid. Proton NMR (500 MHz or 300 MHz; pulse sequence:
s2pul, solvent D20; relax. delay 1.000 sec, pulse 45.0; acq. time 2.345 sec) indicated that all nitrogens in the amine capping unit were fully quaternized.
Cleanin Compositions The present invention further relates to a cleaning composition comprising the modified alkoxylated polyol compound of the present invention. The cleaning compositions can be in any conventional form, namely, in the form of a liquid, powder, granules, agglomerate, paste, tablet, pouches, bar, gel, types delivered in dual-compartment containers, spray or foam detergents, premoistened wipes (i.e., the cleaning composition in combination with a nonwoven material such as that discussed in US 6,121,165, Mackey, et al.), dry wipes (i.e., the cleaning composition in combination with a nonwoven materials, such as that discussed in US 5,980,931, Fowler, et al.) activated with water by a consumer, and other homogeneous or multiphase consumer cleaning product forms.
In addition to cleaning compositions, the compounds of the present invention may be also suitable for use or incorporation into industrial cleaners (i.e. floor cleaners). Often these cleaning compositions will additionally comprise surfactants and other cleaning adjunct ingredients, discussed in more detail below. In one embodiment, the cleaning composition of the present invention is a liquid or solid laundry detergent composition.
In another embodiment, the cleaning composition of the present invention is a hard surface cleaning composition, preferably wherein the hard surface cleaning composition impregnates a nonwoven substrate. As used herein "impregnate" means that the hard surface cleaning composition is placed in contact with a nonwoven substrate such that at least a portion of the nonwoven substrate is penetrated by the hard surface cleaning composition, preferably the hard surface cleaning composition saturates the nonwoven substrate.
In another embodiment the cleaning composition is a liquid dish cleaning composition, such as liquid hand dishwashing compositions, solid automatic dishwashing cleaning compositions, liquid automatic dishwashing cleaning compositions, and tab/unit does forms of automatic dishwashing cleaning compositions.
The cleaning composition may also be utilized in car care compositions, for cleaning various surfaces such as hard wood, tile, ceramic, plastic, leather, metal, glass.
This cleaning composition could be also designed to be used in a personal care composition such as shampoo composition, body wash, liquid or solid soap and other cleaning composition in which surfactant comes into contact with free hardness and in all compositions that require hardness tolerant surfactant system, such as oil drilling compositions.
Modified Alkoxylated Pol~ol Com ounds The cleaning composition of the present invention may comprise from about 0.005% to about 30%, and such as from about 0.01% to about 10%, further such as from about 0.05% to about 5% by weight of the cleaning composition of a modified polyol compound as described herein.
Surfactants - The cleaning composition of the present invention may comprise a surfactant or surfactant system comprising surfactants selected from nonionic, anionic, cationic, ampholytic, zwitterionic, semi-polar nonionic surfactants; and other adjuncts such as alkyl alcohols, or mixtures thereof. The cleaning composition of the present invention further comprises from about from about 0.01% to about 90%, and such as from about 0.01% to about 80%, further such as from about 0.05% to about 50%, more further such as from about 0.05% to about 40% by weight of the cleaning composition of a surfactant system having one or more surfactants.
Anionic Surfactants Nonlimiting examples of anionic surfactants useful herein include: C8-C,8 alkyl benzene sulfonates (LAS); Clo-Czo primary, branched-chain and random alkyl sulfates (AS); C,o-Cis secondary (2,3) alkyl sulfates; C,o-C,$ alkyl alkoxy sulfates (AExS) wherein x is from 1-30; C,o-Ci$ alkyl alkoxy carboxylates comprising 1-5 ethoxy units; mid-chain branched alkyl sulfates as discussed in US 6,020,303 and US 6,060,443; mid-chain branched alkyl alkoxy sulfates as discussed in US 6,008,181 and US 6,020,303; modified alkylbenzene sulfonate (MLAS) as discussed in WO 99/05243, WO 99/05242 and WO 99/05244; methyl ester sulfonate (MES); and alpha-olefin sulfonate (AOS).
Nonionic Surfactants Non-limiting examples of nonionic surfactants include: ClZ-C,8 alkyl ethoxylates, such as, NEODOL~ nonionic surfactants from Shell; C6-C,2 alkyl phenol alkoxylates wherein the alkoxylate units are a mixture of ethyleneoxy and propyleneoxy units; C,2-C18 alcohol and C6-C,Z
alkyl phenol condensates with ethylene oxide/propylene oxide block alkyl polyamine ethoxylates such as PLURONIC~ from BASF; C,4-Czz mid-chain branched alcohols, BA, as discussed in US
The present invention further relates compounds, processes, cleaning compositions, and methods of using said compounds and compositions characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties is replaced by and thus further comprises an anionic capping unit and at least one of the hydroxy moieties is substituted by a quaternary amine capping unit.
The present invention further relates compounds, processes, cleaning compositions, and methods of using said compounds and compositions characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties is replaced by and thus further comprises an anionic capping unit, at least one of the hydroxy moieties is substituted by an amine capping unit and at least one of the hydroxy moieties is substituted by a quaternary amine capping unit.
DETAILED DESCRIPTION OF THE INVENTION
There exists a need for materials that are relatively easy to manufacture from sustainable and readily available raw materials, which may be broadly tuned to address specific formidability and performance requirements.
Polyol compounds such as sugar based materials and polyethylene/polypropylene glycol materials axe sustainable and readily available raw materials that lend themselves to be broadly tuned to address specific formulability and performance requirements. As used herein "tune"
means having the ability to manipulate the chemical structure of the polyol compounds to achieve distinguishing chemical functionality. For example, an alkoxylated polyol compound modified by comprising an anionic capping unit is a tuned structure giving desired characteristics for specific formulability and performance requirements. Another example, an allcoxylated polyol compound modified by comprising an anionic capping unit and amine capping unit is a tuned structure giving desired characteristics. Another example is when an alkoxylated polyol compound is modified by comprising an anionic capping unit and a quaternary amine capping unit, is a tuned structure giving desired characteristics. Finally another example may contain both elements of the two examples, thus containing an anionic capping unit and an amine and quaternary amine capping unit.
The polyol compounds useful in the present invention comprises at least three hydroxy moieties, preferably more than three hydroxy moieties. Most preferably six or more hydroxy moieties. At least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy (E0), propoxy (PO), butoxy (BO) and mixtures thereof preferably ethoxy and propoxy moieties, more preferably ethoxy moieties. The average degree of alkoxylation is from about 1 to about 100, preferably from about 4 to about 60, more preferably from about 10 to about 40. Alkoxylation is preferably block alkoxylation.
The polyol compounds useful in the present invention further have at least one of the alkoxy moieties comprising at least one anionic capping unit. Further modifications or tuning of the compound may occur, but one anionic capping unit must be present in the compound of the present invention. One embodiment comprises more than one hydroxy moiety further comprising an alkoxy moiety having an anionic capping unit. For example formula (I):
O(EO)xH O(EO)XS03Na+
Na+
+Na 03 +Na 03Sx(OE)O O(EO)XS03Na+
formula (I) wherein x of formula (I) is from about 1 to about 100, or such as from about 10 to about 40.
Suitable anionic capping unit include sulfate, sulfosuccinate, succinate, maleate, phosphate, phthalate, sulfocarboxylate, sulfodicarboxylate, propanesultone, 1,2-disulfopropanol, sulfopropylamine, sulphonate, monocarboxylate, methylene carboxylate, ethylene carboxylate, carbonates, mellitic, pyromellitic, sulfophenol, sulfocatechol, disulfocatechol, tartrate, citrate, acrylate, methacrylate, poly acrylate, poly acrylate-maleate copolymer, and mixtures thereof.
Preferably the anionic capping units are sulfate, sulfosuccinate, succinate, maleate, sulfonate, methylene carboxylate and ethylene carboxylate.
Suitable polyol compounds for starting materials for use in the present invention include maltitol, sucrose, xylitol, glycerol, pentaerythitol, glucose, maltose, matotriose, maltodextrin, maltopentose, maltohexose, isomaltulose, sorbitol, poly vinyl alcohol, partially hydrolyzed polyvinylacetate, xylan reduced maltotriose, reduced maltodextrins, polyethylene glycol, polypropylene glycol, polyglycerol, diglycerol ether and mixtures thereof.
Good examples include the polyol compound being selected as sorbitol, maltitol, sucrose, xylan, polyethylene glycol, polypropylene glycol and mixtures thereof. Another group for the polyol compound is sorbitol, maltitol, sucrose, xylan, and mixtures thereof.
Tuning of the polyol compounds can be derived from one or more modifications, dependant upon the desired formidability and performance requirements. Tuning requires anionic modifications and can include incorporating a cationic or zwitterionic charge modifications to the polyol compounds.
In one embodiment of the present invention, at least one hydroxy moiety comprises an alkoxy moiety, wherein the alkoxy moiety further comprises at least one anionic capping unit.
In another embodiment of the present invention, at least one hydroxy moiety comprises an alkoxy moiety, wherein the alkoxy moiety further comprises more than one anionic capping unit, wherein at least one anionic capping unit, but less than all anionic capping units, is then selectively substituted by a amine capping unit. The amine capping unit is selected from a primary amine containing capping unit, a secondary amine containing capping unit, a tertiary amine containing capping unit, and mixtures thereof.
Suitable primary amines for the primary amine containing capping unit include monoamines, diamine, triamine, polyamines, and mixtures thereof. Suitable secondary amines for the secondary amine containing capping unit include monoamines, diamine, triamine, polyamines, and mixtures thereof. Suitable tertiary amines for the tertiary amine containing capping unit include monoamines, diamine, triamine, polyamines, and mixtures thereof.
Suitable monoamines, diamines, triamines or polyamines for use in the present invention include ammonia, methyl amine, dimethylamine, ethylene diamine, dimethylaminopropylamine, bis dimethylaminopropylamine (bis DMAPA), hexemethylene diamine, benzylamine, isoquinoline, ethylamine, diethylamine, dodecylamine, tallow triethylenediamine, mono substituted rnonoamine, monosubstituted diamine, monosubstituted podyamine, disubstituted monoamine, disubstiuted diamine, disubstituted polyamine, trisubstituted triamine, tri-substituted polyamine, multisubstituted polyamine comprising more than three substitutions provided at least one nitrogen contains a hydrogen, and mixtures thereof.
In another embodiment of the 'present invention, at least one of nitrogens in the amine capping unit is quaternized. As used herein "quaternized" means that the amine capping unit is given a positive charge through quaternization or protonization of the amine capping unit. For example, bis-DMAPA contains three nitrogens, only one of the nitrogens need be quaternized.
However, it is preferred to have all nitrogens quaternized on any given amine capping unit.
The tuning or modification may be combined depending upon the desired formulability and performance requirements. Non-limiting examples of modified polyol compounds of the present invention include:
+ +
(CHz)zN(CHs)z(CHz)sN(CH3)a ~3 formula (II)wherein x of formula (I) is from about 1 to about 100; and such as from about 10 to about 40.
+ +
+ + O(EOya(CHz)zN(CH3)z(CHz)~(CHs)3 + +
O (EO)~ 4(CH~ZN(CH3~(CI~)3N(CH3)3 _ ~ 8 Cl ~~h5s~3 N3+
5H O ~O(~hsS03'Na ~(EO), sS03'Na formula (III) ~'3S~.s(~E~'~~ r~ ~ ~ $ Cl + +
~~~~~15~U3 formula (IV) Process of Making The present invention also relates to a process fox making the compound of the present invention. The process for making the compound of the present invention comprises the optional step of alkoxylating a polyol compound comprising at least three hydroxy moieties such that the average degree of alkoxylation of at least one hydroxy moiety is between about 1 and about 100;
and such as from about 4 to about 60; further such as from about 10 to about 40; to form an alkoxylated polyol comprising at least one alkoxy moiety. Alternatively, an alkoxylated polyol, such as CAS 52625-13-5, a propoxylated sorbitol or sorbitol polyoxy ethylene ether available + +
~fECh, afCI-~~~~fGI~~N(CFi~?~
from Lipo Chemicals Inc., may be used as the starting material of the present invention. If the average degree of alkoxylation is not a desired level, an alkoxylation step may be used to achieve the desired degree of alkoxylation from about 1 to about 100, and such as from about 4 to about 60; further such as from about 10 to about 40. Next, the process comprises the step of reacting at least one alkoxy moiety of the compound with an anionic capping unit to form an anionic alkoxylated polyol, although more anionic capping units may be selected.
In one embodiment the process comprises another step of substituting at least one anionic capping unit of the anionic alkoxylated polyol with an amine capping unit to form an anionic aminated alkoxylated polyol. In this process only certain anionic capping units may be substituted such as sulfate, phosphate and carbonate. The process may further comprise the step of quaternizing at least one of the nitrogens in the amine capping of the anionic aminated alkoxylated polyol to form a zwitterionic alkoxylated polyol. Quaternization can be performed on any of the anionic aminated alkoxylated polyols. In one embodiment, the process comprises the step of alkoxylating some or most of the hydroxy moieties of the polyol such that the degree of alkoxylation is from about 1 to about 100; and such as from about 4 to about 60, further such as from about 10 to about 40; to form an alkoxylated polyol. The process further comprises the step of reacting the alkoxy moiety of the alkoxylated polyol with at least one anionic capping unit containing as least one of the following anionic groups; sulfate, phosphate and carbonate; to form an anionic alkoxylated polyol. The process may partially or completely react the alkoxy moiety of the alkoxylated polyol with an anionic capping unit. It is also understood that anionic capping units other than sulfate, phosphate or carbonate may also be present in the anionic alkoxylated polyol. Preferably all alkoxy moieties comprise an anionic capping unit.
Optionally, the process comprises the step of substituting the anionic capping unit with an amine capping unit selected from sulfate, phosphate and carbonate and mixtures thereof, to form an aminated anionic alkoxylated polyol (scheme I below). The substitution of the anionic capping units present with an amine capping unit may be partial or complete.
Preferably the subsitution of the anionic capping unit with the amine capping unit is partial forming an anionic aminated alkoxylated polyol.
Optionally, the process also comprises the process of providing an aminated alkoxylated polyol by direct amination of the alkoxylated polyol using catalytic amination (scheme II below) Optionally, the process may further comprise the step of quaternizing at least one of the nitrogens of the amine capping unit of the anionic aminated alkoxylated polyol forming a zwitterionic alkoxylated polyol. The quaternization of the amine capping unit of the anionic aminated alkoxylated polyol may be partial or complete. In one embodiment, the quaternization is partial. In another embodiment, the quaternization is complete. The quaternization of the nitrogens of the amine capping unit may be partial or complete, preferably complete. A
nonlimiting synthesis scheme is exemplified in Synthesis Scheme I and Synthesis Scheme II
below:
Synthesis Scheme I Anionic aminated alkoxylated polyol H(OE)x0 off off 6 times x EO o(EO),~H
OH O(EO)XH
STEP 1 H Base Catalyst H(oE)xo OH OH H(OE)x0 O(EO)xH
H(OE)x0 +Na 05S(OE)x0 p(EO)KS03Na+
p(~7hH
6 ClS03H o(EO)~SO,Na+
STEP 2 H(pE)x0 ~~)xH ~ +Na 03S(OE)X
CHZCIz Na035(OE~ EO SO Na H(OE)x0 O(HO)xH
+Na03S(OE)XO O(EO)~.S03Na+ 3 (CH3)2NH (CHy~NCHzCHZ(OE)x.~0 O(EO)nSO3Na+
STEP 3 +Na'03S(OE)n O(EO)xS03Na+ ~ O(EO)K_iCHZCHZN(CHy)z Na OgS(OE)x ~ Heatl Pressure ~
+Na03S(OE~ ~EO)xS03Na+ ' 3 OSO Na+ (Cf~~NCH2CH2(OE)x_~~O)"SD3Na+
(CI~)zNCHZCHz(OE~_i0 ~)%S~Na' (CHy)3NCH2CH2(OE~_~ O
EO)KSO~
3 (CH30)ZS02. k STEP 4 EO)x_~CHpCHyN(CH3)Z EO)x.~CHZCH2N(CH~)~
+Na-03S(OB)x ~ b,s(OE)xo (CH3)7NCH2CH2(OE~_i o(EO)xs~Na+ Heat/H20 (CHy)3+CHzCHa(OE~n a EO)xSOJ
The process rnay comprise optionally Step 1, Step 2, and optionally, Step 3 and 4. The step to providing the anionic aminated alkoxylated polyol via a neucleophilic substitution of sulfate moieties by an amine capping unit should be noted. This is a nonlimiting example as phosphate or carbonate groups may also be used for substitution by an amine capping unit.
Synthesis Scheme II:
H(OE~O EO
off OH 6 times x EO « )'~
OH O(EO)TI-I
STEP 1 H H(OE~p Base Catalyst OH OH H(OE~O O(EO),~H
H(OE~O p(~~H
NH3 HZNCH2CHz(OE~.iO p EO H
STEP 2 «HO~H > ( )x H(OE~O See US 5003107 (EO)x.,CH2cHZNH2 H(OE~
H(pE~p o(EO~H or US 23139289A1 by Huntsman for HZNCH2CHz(OE~_~~O)xH
procedure to reapply HZNCHzCHz(OE)x.ip O(EO)xH (CHs)aNCHZCHZ(pE)x.i0 O(EO)XH
+
O(EO)x_~CHZCHZNHZ 9 (CH30)ZSO2. O(EO)x_~CHZCHZN(CH3)3 STEP 3 H(OE~ ---~ H(OE~
HZNCHZCHZ(OE~_~ EO)xH base (pH3hNCHxCHz(OE)x_~ Ep)xH
+
+ 9 CH30S03Na (CH3)3NCHZCH2(OE~.iO p(EO)xH
+ +
O(EO)X_iCH2CHZN(CH3)3 Transsulfation (cH,),NCHzcHz(oEk_,o ~~xs~.
STEP 4 H(pE)x HZ~ EO)x,~CFizCH2N(CH~)3 (CH3)yNCHZCH2(OE~_~ Ep)xH -O~S(OE)x0 + Heat (CH~)~+CH2CHz(OE~_~ O(~)xSO;
+ 9 CH30S03Na Scheme II is distinguished from Scheme I in two areas; (1) direct substitution of the terminal hydroxy moieties is accomplished by catalytic oxidationlreduction using metal catalysts and hydrogen; (2) sulfation is carried out after amination and quatemization by transulfation as disclosed in LTS 6,452,035. A zwitterionic alkoxylated polyol of the same composition may be prepared by either Scheme I or Scheme II above. One of skill in the art will recognized that other amine capping units may be used, including but not limited to ammonia or dimethylaminopropylamine.
A specific description of the process of the present invention is described in more detail below.
Ethoxylation of Polyol Ethoxylation of the polyol, such as sorbitol, may be completed by any known technique, such as that described in EP 174436 A1 Propoxylation and butoxylation may also be completed by known techniques.
Add sorbitol (17.5g, 0.0962 mol) to an autoclave, purge the autoclave with nitrogen, heat sorbitol to 110-120°C; autoclave stirred and apply vacuum to about 20 mmHg.
Vacuum is continuously applied while the autoclave is cooled to about 110-120° C. while introducing 6.2g of a 25% sodium methoxide in methanol solution (0.0288 moles, to achieve a 5% catalyst loading based upon hydroxy moieties). The methanol from the methoxide solution is removed from the autoclave under vacuum. A device is used to monitor the power consumed by the agitator. The agitator power is monitored along with the temperature and pressure. Agitator power and temperature values gradually increase as methanol is removed from the autoclave and the viscosity of the mixture increases and stabilizes in about 1.5 hours indicating that most of the methanol has been removed. The mixture is further heated and agitated under vacuum for an additional 30 minutes.
Vacuum is removed and the autoclave is cooled to or kept at 110° C.
while it is being charged with nitrogen to 1725 kPa (250 psia) and then vented to ambient pressure. The autoclave is charged to 1380 kPa (200 psia) with nitrogen. Ethylene oxide is added to the autoclave incrementally while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate while maintaining the temperature between 110 and 120° C. and limiting any temperature increases due to reaction exotherm. After the addition of 483g of ethylene oxide (10.97 mol, resulting in a total of 19 moles of ethylene oxide per mol of OH), the temperature is increased to I20° C. and the mixture stirred for an additional 2 hours.
The reaction mixture is then collected into a 22 L three neck round bottomed flask purged with nitrogen. The strong alkali catalyst is neutralized by slow addition of 2.8g methanesulfonic acid (0.00288 moles) with heating (110° C.) and mechanical stirring.
The reaction mixture is then purged of residual ethylene oxide and deodorized by sparging an inert gas (argon or nitrogen) into the mixture through a gas dispersion frit while agitating and heating the mixture to 120° C. for 1 hour. The final reaction product, approximately SOOg, is cooled slightly, and poured into a glass container purged with nitrogen for storage.
Alternatively, polyol may be purchased with a degree of alkoxylation that is at or below that desired, such as CAS S262S-13-S, a propoxylated sorbitol or sorbitol polyoxy ethylene ether available from Lipo Chemicals Inc. Wherein the desired degree of alkoxylation is achieved by the processes known and/or described above.
Sulfation of Sorbitol EO,~d (Average of 19 EO moieties per hydroxy moiety) Weigh into a SOOmI Erlenmeyer flask Sorbitol El4 (299.7g, O.OS8 mol) and methylene chloride (300g) ("the solution") . Equip the flask with a magnetic stirring bar and stir until complete dissolution. Place the flask in an ice bath until the solution reaches about 10°C. Stir vigorous while slowing pouring chlorosulfonic acid (48.3g, 0.415 mol) over the period of about S
minutes to form a reaction solution. Stir the reaction solution in the ice bath for 1.5 hours.
Place a solution of sodium methoxide (197g of 2S% in methanol) in SOg of methylene chloride in a IL Erlenmeyer flask ("base solution") and chill in an ice bath until the temperature of the solution reaches about 10°C. Stir the base solution vigorous using a magnetic stirring bar.
Slowly pour the reaction solution into the base solution over a period of about 3 minutes. A mild exotherm should be observed. The resulting solution becomes milky as salts form. After addition is complete, measure the pH to be about 12. Add to this resulting solution about 100 ml of distilled water, and transfer the resulting emulsion to a 1L round bottom flask and use a rotary evaporator at 50°C to strip, in portions, to obtain a clear solution.
Transfer the clear solution to a Kulgelrohr apparatus. At 60°C and 133 Pa (lmm Hg) strip the solution to yield 366g of off white waxy solid, 90% active (10% salts).
Carbon NMR spectrum (500 MHz; pulse sequence: s2pul, solvent D20; relax. delay 0.300 sec, pulse 45.0; acq. time 1.090 sec) shows an absence of alcohol groups at about 60ppm and the emergence of a new peak at about 67ppm consistent with formation of the end group sulfate. Proton NMR spectrum (500 MHz or 300 MHz; pulse sequence: s2pul, solvent DzO;
relax. delay 1.000 sec, pulse 45.0; acq. time 2.345 sec) shows a new peak at about 4ppm which was integrated against the ethoxy group protons at about 3.Sppm and is consistent with the molecule having 6 end group sulfates.
Example 2: Amination of Sorbitol EO"n Hexasulfate Of Example 1 Weigh into a 200m1 glass liner sorbitol EO"4 hexasulfate (61.3g of 90% active, 0.0095 mol) and 3-(dimethylamino)propylamine ("DMAPA" 18.5g, 0.181 mol). Heat the liner in a rocking autoclave at 152 kPa (150 prig) under nitrogen until the temperature reaches 165°C and hold at 165°C for 2 hours. Cool to room temperature (20 - 25°C). Take the material up in 150 ml of methylene chloride and centrifuge to separate the salts. Transfer the supernatant to a SOOmI round bottom flask and strip the supernatant on a rotary evaporator at SO°C
until most (less than 5 mL) of the solvent is removed. Heat on a Kugelrohr apparatus at 120°C and 133 Pa (lmm Hg) for 30 minutes to remove excess amine to afford 47.8g of brown hard solid. Proton NMR
(500 MHz or 300 MHz; pulse sequence: s2pul, solvent D20; relax. delay 0.300 sec, pulse 45.0; acq. time 3.744 sec) indicated about 3 sulfates and about 2 DMAPA per molecule.
Examine 3: Quaternization of Amine Containing Sulfate Of Example 2 Dissolve an aminated Sorbitol EO,Ia in 100g of methylene chloride in a SOOmI
round bottom flask equipped with a magnestic stirring bar and chill in an ice bath until the temperature reaches 10°C. Adjust the solution to a pH 12 with sodium methoxide (25%
solution in methanol).
Add to the solution methyl iodide (lS.Og, 0.106mo1). Stopper the flask and stir the solution overnight (about 14 hours). Strip the solution on a Kugelrohr apparatus at 50°C and 133 Pa (lmm Hg) to afford 66g of tacky brown solid. Proton NMR (500 MHz or 300 MHz; pulse sequence:
s2pul, solvent D20; relax. delay 1.000 sec, pulse 45.0; acq. time 2.345 sec) indicated that all nitrogens in the amine capping unit were fully quaternized.
Cleanin Compositions The present invention further relates to a cleaning composition comprising the modified alkoxylated polyol compound of the present invention. The cleaning compositions can be in any conventional form, namely, in the form of a liquid, powder, granules, agglomerate, paste, tablet, pouches, bar, gel, types delivered in dual-compartment containers, spray or foam detergents, premoistened wipes (i.e., the cleaning composition in combination with a nonwoven material such as that discussed in US 6,121,165, Mackey, et al.), dry wipes (i.e., the cleaning composition in combination with a nonwoven materials, such as that discussed in US 5,980,931, Fowler, et al.) activated with water by a consumer, and other homogeneous or multiphase consumer cleaning product forms.
In addition to cleaning compositions, the compounds of the present invention may be also suitable for use or incorporation into industrial cleaners (i.e. floor cleaners). Often these cleaning compositions will additionally comprise surfactants and other cleaning adjunct ingredients, discussed in more detail below. In one embodiment, the cleaning composition of the present invention is a liquid or solid laundry detergent composition.
In another embodiment, the cleaning composition of the present invention is a hard surface cleaning composition, preferably wherein the hard surface cleaning composition impregnates a nonwoven substrate. As used herein "impregnate" means that the hard surface cleaning composition is placed in contact with a nonwoven substrate such that at least a portion of the nonwoven substrate is penetrated by the hard surface cleaning composition, preferably the hard surface cleaning composition saturates the nonwoven substrate.
In another embodiment the cleaning composition is a liquid dish cleaning composition, such as liquid hand dishwashing compositions, solid automatic dishwashing cleaning compositions, liquid automatic dishwashing cleaning compositions, and tab/unit does forms of automatic dishwashing cleaning compositions.
The cleaning composition may also be utilized in car care compositions, for cleaning various surfaces such as hard wood, tile, ceramic, plastic, leather, metal, glass.
This cleaning composition could be also designed to be used in a personal care composition such as shampoo composition, body wash, liquid or solid soap and other cleaning composition in which surfactant comes into contact with free hardness and in all compositions that require hardness tolerant surfactant system, such as oil drilling compositions.
Modified Alkoxylated Pol~ol Com ounds The cleaning composition of the present invention may comprise from about 0.005% to about 30%, and such as from about 0.01% to about 10%, further such as from about 0.05% to about 5% by weight of the cleaning composition of a modified polyol compound as described herein.
Surfactants - The cleaning composition of the present invention may comprise a surfactant or surfactant system comprising surfactants selected from nonionic, anionic, cationic, ampholytic, zwitterionic, semi-polar nonionic surfactants; and other adjuncts such as alkyl alcohols, or mixtures thereof. The cleaning composition of the present invention further comprises from about from about 0.01% to about 90%, and such as from about 0.01% to about 80%, further such as from about 0.05% to about 50%, more further such as from about 0.05% to about 40% by weight of the cleaning composition of a surfactant system having one or more surfactants.
Anionic Surfactants Nonlimiting examples of anionic surfactants useful herein include: C8-C,8 alkyl benzene sulfonates (LAS); Clo-Czo primary, branched-chain and random alkyl sulfates (AS); C,o-Cis secondary (2,3) alkyl sulfates; C,o-C,$ alkyl alkoxy sulfates (AExS) wherein x is from 1-30; C,o-Ci$ alkyl alkoxy carboxylates comprising 1-5 ethoxy units; mid-chain branched alkyl sulfates as discussed in US 6,020,303 and US 6,060,443; mid-chain branched alkyl alkoxy sulfates as discussed in US 6,008,181 and US 6,020,303; modified alkylbenzene sulfonate (MLAS) as discussed in WO 99/05243, WO 99/05242 and WO 99/05244; methyl ester sulfonate (MES); and alpha-olefin sulfonate (AOS).
Nonionic Surfactants Non-limiting examples of nonionic surfactants include: ClZ-C,8 alkyl ethoxylates, such as, NEODOL~ nonionic surfactants from Shell; C6-C,2 alkyl phenol alkoxylates wherein the alkoxylate units are a mixture of ethyleneoxy and propyleneoxy units; C,2-C18 alcohol and C6-C,Z
alkyl phenol condensates with ethylene oxide/propylene oxide block alkyl polyamine ethoxylates such as PLURONIC~ from BASF; C,4-Czz mid-chain branched alcohols, BA, as discussed in US
6,150,322; C,4-C22 mid-chain branched alkyl alkoxylates, BAEx, wherein x 1-30, as discussed in US 6,153,577, US 6,020,303 and US 6,093,856; Alkylpolysaccharides as discussed in U.S.
4,565,647 Llenado, issued January 26, 1986; specifically alkylpolyglycosides as discussed in US
4,483,780 and LTS 4,483,779; Polyhydroxy fatty acid amides (GS-base) as discussed in US
5,332,528; and ether capped poly(oxyalkylated) alcohol surfactants as discussed in US 6,482,994 and WO 01/42408.
Cationic Surfactants Non-limiting examples of anionic surfactants include: the quaternary ammonium surfactants, which can have up to 26 carbon atoms include: alkoxylate quaternary ammonium (AQA) surfactants as discussed in US 6,136,769; dimethyl hydroxyethyl quaternary ammonium as discussed in 6,004,922; polyamine cationic surfactants as discussed in WO
98/35002, WO
98/35003, WO 98/35004, WO 98/35005, and WO 98135006; cationic ester surfactants as discussed in US Patents Nos 4,228,042, 4,239,660 4,260,529 and US 6,022,844;
and amino surfactants as discussed in US 6,221,825 and WO 00/47708, specifically amido propyldimethyl amine (APA).
Zwitterionic Surfactants Non-limiting examples of zwitterionic surfactants include: derivatives of secondary and tertiary amines, derivatives of heterocyclic secondary and tertiary amines, or derivatives of quaternary ammonium, quaternary phosphonium or tertiary sulfonium compounds.
See U.S.
4,565,647 Llenado, issued January 26, 1986; specifically alkylpolyglycosides as discussed in US
4,483,780 and LTS 4,483,779; Polyhydroxy fatty acid amides (GS-base) as discussed in US
5,332,528; and ether capped poly(oxyalkylated) alcohol surfactants as discussed in US 6,482,994 and WO 01/42408.
Cationic Surfactants Non-limiting examples of anionic surfactants include: the quaternary ammonium surfactants, which can have up to 26 carbon atoms include: alkoxylate quaternary ammonium (AQA) surfactants as discussed in US 6,136,769; dimethyl hydroxyethyl quaternary ammonium as discussed in 6,004,922; polyamine cationic surfactants as discussed in WO
98/35002, WO
98/35003, WO 98/35004, WO 98/35005, and WO 98135006; cationic ester surfactants as discussed in US Patents Nos 4,228,042, 4,239,660 4,260,529 and US 6,022,844;
and amino surfactants as discussed in US 6,221,825 and WO 00/47708, specifically amido propyldimethyl amine (APA).
Zwitterionic Surfactants Non-limiting examples of zwitterionic surfactants include: derivatives of secondary and tertiary amines, derivatives of heterocyclic secondary and tertiary amines, or derivatives of quaternary ammonium, quaternary phosphonium or tertiary sulfonium compounds.
See U.S.
Patent No. 3,929,678 to Laughlin et al., issued December 30, 1975 at column 19, line 38 through column 22, line 48, for examples of zwitterionic surfactants; betaine, including alkyl dimethyl betaine and cocodimethyl amidopropyl betaine, C$ to Cl8 ( Clz to C~$) amine oxides and sulfo and hydroxy betaines, such as N-alkyl-N,N-dimethylammino-1-propane sulfonate where the alkyl group can be Cg to C,B, Clo to C,4.
Ampholytic Surfactants Non-limiting examples of ampholytic surfactants include: aliphatic derivatives of secondary or tertiary amines, or aliphatic derivatives of heterocyclic secondary and tertiary amines in which the aliphatic radical can be straight- or branched-chain. One of the aliphatic substituents contains at least about 8 carbon atoms, typically from about 8 to about 18 carbon atoms, and at least one contains an anionic water-solubilizing group, e.g.
carboxy, sulfonate, sulfate. See U.S. Patent No. 3,929,678 to Laughlin et al., issued December 30, 1975 at column 19, lines 18-35, for examples of arnpholytic surfactants.
Semi-Polar Nonionic Surfactants Non-limiting examples of semi-polar nonionic surfactants include: water-soluble amine oxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to about 3 carbon atoms; water-soluble phosphine oxides containing one alkyl moiety of from about to about 18 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to about 3 carbon atoms; and water-soluble sulfoxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and a moiety selected from the group consisting of alkyl and hydroxyalkyl moieties of from about 1 to about 3 carbon atoms. See WO 01/32816, US 4,681,704, and US 4,133,779.
Gemini Surfactants Gemini Surfactants are compounds having at least two hydrophobic groups and at least two hydrophilic groups per molecule have been introduced. These have become known as "gemini surfactants" in the literature, e.g., Chemtech, March 1993, pp 30-33, and J. American Chemical Soc., 115, 10083-10090 (1993) and the references cited therein.
Cleaning Adtunct Materials In general, a cleaning adjunct is any material required to transform a cleaning composition containing only the minimum essential ingredients into a cleaning composition useful for laundry, hard surface, personal care, consumer, commercial and/or industrial cleaning purposes. In certain embodiments, cleaning adjuncts are easily recognizable to those of skill in the art as being absolutely characteristic of cleaning products, especially of cleaning products intended for direct use by a consumer in a domestic environment.
The precise nature of these additional components, and levels of incorporation thereof, will depend on the physical form of the cleaning composition and the nature of the cleaning operation for which it is to be used.
The cleaning adjunct ingredients if used with bleach should have good stability therewith.
Certain embodiments of cleaning compositions herein should be boron-free and/or phosphate-free as required by legislation. Levels of cleaning adjuncts are from about 0.00001% to about 99.9%, and such as from about 0.0001% to about 50% by weight of the cleaning compositions. Use levels of the overall cleaning compositions can vary widely depending on the intended application, ranging for example from a few ppm in solution to so-called "direct application" of the neat cleaning composition to the surface to be cleaned.
Quite typically, cleaning compositions herein such as laundry detergents, laundry detergent additives, hard surface cleaners, synthetic and soap-based laundry bars, fabric softeners and fabric treatment liquids, solids and treatment articles of all kinds will require several adjuncts, though certain simply formulated products, such as bleach additives, may require only, for example, an oxygen bleaching agent and a surfactant as described herein. A
comprehensive list of suitable laundry or cleaning adjunct materials can be found in WO 99/05242.
Common cleaning adjuncts include builders, enzymes, polymers not discussed above, bleaches, bleach activators, catalytic materials and the like excluding any materials already defined hereinabove. Other cleaning adjuncts herein can include suds boosters, suds suppressors (antifoams) and the like, diverse active ingredients or specialized materials such as dispersant polymers (e.g., from BASF Corp. or Rohm & Haas) other than those described above, color speckles, silvercare, anti-tarnish and/or anti-corrosion agents, dyes, fillers, germicides, alkalinity sources, hydrotropes, anti-oxidants, enzyme stabilizing agents, pro-perfumes, perfumes, solubilizing agents, carriers, processing aids, pigments, and, for liquid formulations, solvents, chelating agents, dye transfer inhibiting agents, dispersants, brighteners, suds suppressors, dyes, structure elasticizing agents, fabric softeners, anti-abrasion agents, hydrotropes, processing aids, and other fabric care agents, surface and skin care agents. Suitable examples of such other cleaning adjuncts and levels of use are found in U.S. Patent Nos. 5,576,282, 6,306,812 B1 and 6,326,348 B 1.
Method of Use The present invention includes a method for cleaning a surface or fabric. Such method includes the steps of contacting a modified alkoxylated polyol compound of the present invention or an embodiment of the cleaning composition comprising the modified alkoxylated polyol compound of the present invention, in neat form or diluted in a wash liquor, with at least a portion of a surface or fabric then optionally rinsing such surface or fabric.
Preferably the surface or fabric is subjected to a washing step prior to the aforementioned optional rinsing step. For purposes of the present invention, washing includes but is not limited to, scrubbing, and mechanical agitation.
As will be appreciated by one skilled in the art, the cleaning compositions of the present invention are ideally suited for use in home care (hard surface cleaning compositions), personal care and/or laundry applications. Accordingly, the present invention includes a method for cleaning a surface and/or laundering a fabric. The method comprises the steps of contacting a surface and/or fabric to be cleaned/laundered with the modified alkoxylated polyol compound or a cleaning composition comprising the modified alkoxylated polyol compound. The surface may comprise most any hard surface being found in a typical home such as hard wood, tile, ceramic, plastic, leather, metal, glass, or may consist of a cleaning surfaces in a personal care product such as hair and skin. The surface may also include dishes, glasses, and other cooking surfaces. The fabric may comprise most any fabric capable of being laundered in normal consumer use conditions.
The cleaning composition solution pH is chosen to be the most complimentary to a surface to be cleaned spanning broad range of pH, from about 5 to about 11.
For personal care such as skin and hair cleaning pH of such composition preferably has a pH from about 5 to about 8 for laundry cleaning compositions pH of from about 8 to about 10. The compositions are preferably employed at concentrations of from about 200 ppm to about 10,000 ppm in solution.
The water temperatures preferably range from about 5 °C to about 100 °C.
For use in laundry cleaning compositions, the compositions are preferably employed at concentrations from about 200 ppm to about 10000 ppm in solution (or wash liquor). The water temperatures preferably range from about 5°C to about 60°C. The water to fabric ratio is preferably from about 1:1 to about 20:1.
The present invention included a method for cleaning a surface or fabric. Such method includes the step of contacting a nonwoven substrate impregnated with an embodiment of the cleaning composition of the present invention, and contacting the nonwoven substrate with at least a portion of a surface and/or fabric. The method may further comprise a washing step. For purposes of the present invention, washing includes but is not limited to, scrubbing, and mechanical agitation. The method may further comprise a rinsing step.
As used herein "nonwoven substrate" can comprise any conventionally fashioned nonwoven sheet or web having suitable basis weight, caliper (thickness), absorbency and strength characteristics. Examples of suitable commercially available nonwoven substrates include those marketed under the tradename SONTAR.A~ by DuPont and POLYWEB RO by James River Corp.
As will be appreciated by one skilled in the art, the cleaning compositions of the present invention are ideally suited for use in hard surface applications.
Accordingly, the present invention includes a method for cleaning hard surfaces. The method comprises the steps of contacting a hard surface to be cleaned with a hard surface solution or nonwoven substrate impregnated with an embodiment of the cleaning composition of the present invention. The method of use comprises the steps of contacting the cleaning composition with at least a portion of the nonwoven substrate, then contacting a hard surface by the hand of a user or by the use of an implement to which the nonwoven substrate attaches.
As will be appreciated by one skilled in the art, the cleaning compositions of the present invention are ideally suited for use in liquid dish cleaning compositions. The method for using a liquid dish composition of the present invention comprises the steps of contacting soiled dishes with an effective amount, typically from about 0.5 m1. to about 20 ml. (per 25 dishes being treated) of the liquid dish cleaning composition of the present invention diluted in water. Suitable examples may be seen below in Table 5.
Generally, from about 0.01 ml, to about 150 ml. of a liquid dish cleaning composition of the invention is combined with from about 2000 ml. to about 20000 ml of water in a sink having a volumetric capacity in the range of from about 1000 ml. to about 20000 ml..
The soiled dishes are immersed in the sink containing the diluted compositions then obtained, where contacting the soiled surface of the dish with a cloth, sponge, or similar article cleans them. The cloth, sponge, or similar article may be immersed in the detergent composition and water mixture prior to being contacted with the dish surface, and is typically contacted with the dish surface for a period of time ranged from about 1 to about 10 seconds. The contacting of cloth, sponge, or similar article to the dish surface is preferably accompanied by a concurrent scrubbing of the dish surface.
Another method of use will comprise immersing the soiled dishes into a water bath without any liquid dish cleaning composition. A device for absorbing liquid dish cleaning composition, such as a sponge, is placed directly into a separate quantity of undiluted liquid dish cleaning composition for a period of time typically ranging from about 1 to about 5 seconds. The absorbing device, and consequently the undiluted liquid dish cleaning composition, is then contacted individually to the surface of each of the soiled dishes to remove said soiling. The absorbing device is typically contacted with each dish surface for a period of time range from about 1 to about 10 seconds. The contacting of the absorbing device to the dish surface is preferably accompanied by concurrent scrubbing.
As will be appreciated by one skilled in the art, the cleaning compositions of the present invention are also suited for use in personal cleaning care applications.
Accordingly, the present invention includes a method for cleaning skin or hair. The method comprises the steps of contacting a skin / hair to be cleaned with a cleaning solution or nonwoven substrate impregnated with an embodiment of the cleaning compositions discussed herein. The method of use of the nonwoven substrate when contacting skin and hair may be by the hand of a user or by the use of an implement to which the nonwoven substrate attaches.
Other Compositions Other compositions that comprise the compound of the present invention may be used in personal care compositions, such as contact lens solution, used as adhesives, in the vulcanization of rubbers, used in polyurethane manufacturing processes, used in dye compositions, used as an ink composition, used as a dispersant in agricultural applications, such as a dispersant in an antifungal composition, among other compositions.
Formulations Table 1-Li u id Laundr Cleaninompositions C
A
Ingredients [% by wt.]
Linear 10-15 alkylbenzenesulfonate Clz_~s alcohol 1-5 ethoxy (1.l-2.5) sulfate Ciz-i3 alcohol 1-5 ethoxylate ~~_9~
cocodimethyl 0.1-1 amine oxide fatty acid 1-5 citric acid 1-5 Polymer c' 0.5-3 hydroxylated 5-20 castor oil (structurant) Vi~ater, perfumes,ad 100 dyes, and other trace components polymer according to any one of Examples 1-3 and formula I-IVof the present application.
Table 2 Low Sudsin ularundtCleaning Compositions Gran La B C D
Wt% Wt% wt%
C1,_,z Linear alkyl benzene 7 5.1 10.2 sul honate C~z-is tallow alk 1 1 1 1 sulfate C,4-is alk 1 ethox 3.2 3.2 3.2 late EO=7 APA~ 0.940,681.36 silicate builderz 4.05- -Zeolite A3 16.65- -Carbonate4 14.04- -Citric Acid Anh drous2.932.932.93 acrylic acid/maleic 0.97 acid 0.970.97 co of mers Pol mer6 1-5 1-5 1-5 Percarbonate 12.816.1813.25 tetraace leth lenediamine3.645.923.95 1-hydroxyethyidene-l , l - 0.180.180.18 di hos honic acid S,S-(ethylenediamine N,N'- 0.2 0.2 0.2 disuccinic acid) M S04 0.420.420.42 ENZYMES' % article 1.261.261.26 MINORS (perfume, Ad Ad Ad dyes, suds 100 100 100 stabilizers I Ca-so amido propyl dimethyl amine Z Amorphous Sodium Silicate (Si02:Na20; 2.0 ratio) 3 Hydrated Sodium Aluminosilicate of formula NaI2(A102Si02)12~ 27H20 having a primary particle size in the range from 0.1 to 10 micrometers 4Anhydrous sodium carbonate with a particle size between 200~m and 900~m 4:1 acrylic acid/maleic acid, average molecular weigh about 70,000 or 6:4 acrylic acid/maleic acid, average molecular weight about 10,000) ~ polymer accordin to any one of Examples I-3 or formula I-IV of the present invention ~ one or more enzymes such as:
Protease - Proteolytic enzyme, having 3.3% by weight of active enzyme, sold by NOVO Industries A/S
under the tradename SAVINASE~; Proteolytic enzyme, having 4% by weight of active enzyme, as described in WO 95/10591, sold by Genencor Int. Inc.
Alcalase- Proteolytic enzyme, having 5.3% by weight of active enzyme, sold by NOVO Industries A/S
Cellulase - Cellulytic enzyme, having 0.23% by weight of active enzyme, sold by NOVO Industries A/S
under the tradename CAREZYME~.
Amylase - Amylolytic enzyme, having 1.6% by weight of active enzyme, sold by NOVO Industries A/S
under the fradename TERMAMYL 120T~; Amylolytic enzyme, as disclosed in PCT/
US9703635.
Lipase - Lipolytic enzyme, having 2.0% by weight of active enzyme, sold by NOVO Industries A/S under the tradename LIPOLASE~; Lipolytic enzyme, having 2.0% by weight of active enzyme, sold by NOVO
Industries A/S under the tradename LIPOLASE ULTRA.
Endolase - Endoglucanase enzyme, having 1.5% by weight of active enzyme, sold by NOVO Industries A/S.
TableranularLaundCleaning Compositions G
E F G H
wt% wt% wt% wt%
Clo_,z linear 13.4- 15.2-alkyl 15.0 17.2 2.7 2.7 sul honate Csz-sa alkyl ethoxylate.8 .8 .0 .0 EO=9 Builders 18 -- -- --Se uestrantz-- 17 -- --enz me 0.35 0.40 -- --Pol mer3 1-2 1-2 1 1 Carboxy Methyl Cellulose.2 .2 .5 -suds su ressor40.01 0.01 -- --Pol ac 0.80 0.8 0.5 later buffer 4.0 2.0 6.0 6.0 Carbonate 11.0 15.0 8.0 8.0 bri htener0.08 0.08 0.03 0.03 Sodium 65.0 65.0 Sulfate 34.83 32.339 9 Water and Ad Ad Ad Ad minors 100 100 100 100 I sodium tripolyphosphate Zeolite A: Hydrated Sodium Aluminosilicate of formula Nal2(A102Si02)12~ 2~H20 having a primary particle size in the range from 0.1 to 10 micrometers 3. An modified alkoxylated polyol compound according to Examples 1-3 and formula I-IV of the present application 4. suds suppressor 5 Mw=4500 Table 4 Hard Surfa ce Cleanin Com ositions Moor cleaningfloor cleaning ipe solutionolution I J
Wt% wt%
C, I alcohol ethoxylate EO=5 0.03 0.03 Sodium C8 Sulfonate0.01 0.01 Propylene Glycol n-Butyl 2 2 Ether 2-Phenox ethanol 0.05 0.05 Ethanol 3 Pol mere 0.015 0.015 2-Dimethylamino-2-methyl-2- ro anol DMAMP 0.01 0.01 erfume 0.01-0.060.01-0.06 Suds su ressor2 0.003 0.003 2-methyl-4-isothaizolin-3 --one 0.015 + chloro derivative Water and minors Ad 100 Ad 100 ~
polymer according to Examples 1-3 and formula I-IVof the present application.
Z such as Dow Corning AF Emulsion or polydimethyl siloxane Table 5 Liauid Dishwashing Cleaning Composition K L M
C,z-,3 alcohol ethox late sulfate 26 23 24 EO=0.6 Amine Oxide 5.8 5.8 5.8 C8_,z alcohol ethox late EO=8 2 2 2 Ethanol 2 2 2 Sodium cumene sulfonate 1.80 1.80 1.80 NaCI 1,4 1.4 1.4 M Clz 0.2 0.2 0.2 Suds Booster' 0.2 0.2 0.2 Pol merz 0.8 0.8 0.8 Water & other trace components (i.e.,dye,ad ad ad perfume, 100 100 100 diamine, etc.
' as described in US 6,645,925 Bl 2 a polymer according to Examples 1- 3 and formula I-IVof the present invention.
All documents cited in the Detailed Description of the Invention are, are, in relevant part, incorporated herein by reference; the citation of any document is not to be construed as an admission that it is prior art with respect to the present invention.
While particular embodiments of the present invention have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.
Ampholytic Surfactants Non-limiting examples of ampholytic surfactants include: aliphatic derivatives of secondary or tertiary amines, or aliphatic derivatives of heterocyclic secondary and tertiary amines in which the aliphatic radical can be straight- or branched-chain. One of the aliphatic substituents contains at least about 8 carbon atoms, typically from about 8 to about 18 carbon atoms, and at least one contains an anionic water-solubilizing group, e.g.
carboxy, sulfonate, sulfate. See U.S. Patent No. 3,929,678 to Laughlin et al., issued December 30, 1975 at column 19, lines 18-35, for examples of arnpholytic surfactants.
Semi-Polar Nonionic Surfactants Non-limiting examples of semi-polar nonionic surfactants include: water-soluble amine oxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to about 3 carbon atoms; water-soluble phosphine oxides containing one alkyl moiety of from about to about 18 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to about 3 carbon atoms; and water-soluble sulfoxides containing one alkyl moiety of from about 10 to about 18 carbon atoms and a moiety selected from the group consisting of alkyl and hydroxyalkyl moieties of from about 1 to about 3 carbon atoms. See WO 01/32816, US 4,681,704, and US 4,133,779.
Gemini Surfactants Gemini Surfactants are compounds having at least two hydrophobic groups and at least two hydrophilic groups per molecule have been introduced. These have become known as "gemini surfactants" in the literature, e.g., Chemtech, March 1993, pp 30-33, and J. American Chemical Soc., 115, 10083-10090 (1993) and the references cited therein.
Cleaning Adtunct Materials In general, a cleaning adjunct is any material required to transform a cleaning composition containing only the minimum essential ingredients into a cleaning composition useful for laundry, hard surface, personal care, consumer, commercial and/or industrial cleaning purposes. In certain embodiments, cleaning adjuncts are easily recognizable to those of skill in the art as being absolutely characteristic of cleaning products, especially of cleaning products intended for direct use by a consumer in a domestic environment.
The precise nature of these additional components, and levels of incorporation thereof, will depend on the physical form of the cleaning composition and the nature of the cleaning operation for which it is to be used.
The cleaning adjunct ingredients if used with bleach should have good stability therewith.
Certain embodiments of cleaning compositions herein should be boron-free and/or phosphate-free as required by legislation. Levels of cleaning adjuncts are from about 0.00001% to about 99.9%, and such as from about 0.0001% to about 50% by weight of the cleaning compositions. Use levels of the overall cleaning compositions can vary widely depending on the intended application, ranging for example from a few ppm in solution to so-called "direct application" of the neat cleaning composition to the surface to be cleaned.
Quite typically, cleaning compositions herein such as laundry detergents, laundry detergent additives, hard surface cleaners, synthetic and soap-based laundry bars, fabric softeners and fabric treatment liquids, solids and treatment articles of all kinds will require several adjuncts, though certain simply formulated products, such as bleach additives, may require only, for example, an oxygen bleaching agent and a surfactant as described herein. A
comprehensive list of suitable laundry or cleaning adjunct materials can be found in WO 99/05242.
Common cleaning adjuncts include builders, enzymes, polymers not discussed above, bleaches, bleach activators, catalytic materials and the like excluding any materials already defined hereinabove. Other cleaning adjuncts herein can include suds boosters, suds suppressors (antifoams) and the like, diverse active ingredients or specialized materials such as dispersant polymers (e.g., from BASF Corp. or Rohm & Haas) other than those described above, color speckles, silvercare, anti-tarnish and/or anti-corrosion agents, dyes, fillers, germicides, alkalinity sources, hydrotropes, anti-oxidants, enzyme stabilizing agents, pro-perfumes, perfumes, solubilizing agents, carriers, processing aids, pigments, and, for liquid formulations, solvents, chelating agents, dye transfer inhibiting agents, dispersants, brighteners, suds suppressors, dyes, structure elasticizing agents, fabric softeners, anti-abrasion agents, hydrotropes, processing aids, and other fabric care agents, surface and skin care agents. Suitable examples of such other cleaning adjuncts and levels of use are found in U.S. Patent Nos. 5,576,282, 6,306,812 B1 and 6,326,348 B 1.
Method of Use The present invention includes a method for cleaning a surface or fabric. Such method includes the steps of contacting a modified alkoxylated polyol compound of the present invention or an embodiment of the cleaning composition comprising the modified alkoxylated polyol compound of the present invention, in neat form or diluted in a wash liquor, with at least a portion of a surface or fabric then optionally rinsing such surface or fabric.
Preferably the surface or fabric is subjected to a washing step prior to the aforementioned optional rinsing step. For purposes of the present invention, washing includes but is not limited to, scrubbing, and mechanical agitation.
As will be appreciated by one skilled in the art, the cleaning compositions of the present invention are ideally suited for use in home care (hard surface cleaning compositions), personal care and/or laundry applications. Accordingly, the present invention includes a method for cleaning a surface and/or laundering a fabric. The method comprises the steps of contacting a surface and/or fabric to be cleaned/laundered with the modified alkoxylated polyol compound or a cleaning composition comprising the modified alkoxylated polyol compound. The surface may comprise most any hard surface being found in a typical home such as hard wood, tile, ceramic, plastic, leather, metal, glass, or may consist of a cleaning surfaces in a personal care product such as hair and skin. The surface may also include dishes, glasses, and other cooking surfaces. The fabric may comprise most any fabric capable of being laundered in normal consumer use conditions.
The cleaning composition solution pH is chosen to be the most complimentary to a surface to be cleaned spanning broad range of pH, from about 5 to about 11.
For personal care such as skin and hair cleaning pH of such composition preferably has a pH from about 5 to about 8 for laundry cleaning compositions pH of from about 8 to about 10. The compositions are preferably employed at concentrations of from about 200 ppm to about 10,000 ppm in solution.
The water temperatures preferably range from about 5 °C to about 100 °C.
For use in laundry cleaning compositions, the compositions are preferably employed at concentrations from about 200 ppm to about 10000 ppm in solution (or wash liquor). The water temperatures preferably range from about 5°C to about 60°C. The water to fabric ratio is preferably from about 1:1 to about 20:1.
The present invention included a method for cleaning a surface or fabric. Such method includes the step of contacting a nonwoven substrate impregnated with an embodiment of the cleaning composition of the present invention, and contacting the nonwoven substrate with at least a portion of a surface and/or fabric. The method may further comprise a washing step. For purposes of the present invention, washing includes but is not limited to, scrubbing, and mechanical agitation. The method may further comprise a rinsing step.
As used herein "nonwoven substrate" can comprise any conventionally fashioned nonwoven sheet or web having suitable basis weight, caliper (thickness), absorbency and strength characteristics. Examples of suitable commercially available nonwoven substrates include those marketed under the tradename SONTAR.A~ by DuPont and POLYWEB RO by James River Corp.
As will be appreciated by one skilled in the art, the cleaning compositions of the present invention are ideally suited for use in hard surface applications.
Accordingly, the present invention includes a method for cleaning hard surfaces. The method comprises the steps of contacting a hard surface to be cleaned with a hard surface solution or nonwoven substrate impregnated with an embodiment of the cleaning composition of the present invention. The method of use comprises the steps of contacting the cleaning composition with at least a portion of the nonwoven substrate, then contacting a hard surface by the hand of a user or by the use of an implement to which the nonwoven substrate attaches.
As will be appreciated by one skilled in the art, the cleaning compositions of the present invention are ideally suited for use in liquid dish cleaning compositions. The method for using a liquid dish composition of the present invention comprises the steps of contacting soiled dishes with an effective amount, typically from about 0.5 m1. to about 20 ml. (per 25 dishes being treated) of the liquid dish cleaning composition of the present invention diluted in water. Suitable examples may be seen below in Table 5.
Generally, from about 0.01 ml, to about 150 ml. of a liquid dish cleaning composition of the invention is combined with from about 2000 ml. to about 20000 ml of water in a sink having a volumetric capacity in the range of from about 1000 ml. to about 20000 ml..
The soiled dishes are immersed in the sink containing the diluted compositions then obtained, where contacting the soiled surface of the dish with a cloth, sponge, or similar article cleans them. The cloth, sponge, or similar article may be immersed in the detergent composition and water mixture prior to being contacted with the dish surface, and is typically contacted with the dish surface for a period of time ranged from about 1 to about 10 seconds. The contacting of cloth, sponge, or similar article to the dish surface is preferably accompanied by a concurrent scrubbing of the dish surface.
Another method of use will comprise immersing the soiled dishes into a water bath without any liquid dish cleaning composition. A device for absorbing liquid dish cleaning composition, such as a sponge, is placed directly into a separate quantity of undiluted liquid dish cleaning composition for a period of time typically ranging from about 1 to about 5 seconds. The absorbing device, and consequently the undiluted liquid dish cleaning composition, is then contacted individually to the surface of each of the soiled dishes to remove said soiling. The absorbing device is typically contacted with each dish surface for a period of time range from about 1 to about 10 seconds. The contacting of the absorbing device to the dish surface is preferably accompanied by concurrent scrubbing.
As will be appreciated by one skilled in the art, the cleaning compositions of the present invention are also suited for use in personal cleaning care applications.
Accordingly, the present invention includes a method for cleaning skin or hair. The method comprises the steps of contacting a skin / hair to be cleaned with a cleaning solution or nonwoven substrate impregnated with an embodiment of the cleaning compositions discussed herein. The method of use of the nonwoven substrate when contacting skin and hair may be by the hand of a user or by the use of an implement to which the nonwoven substrate attaches.
Other Compositions Other compositions that comprise the compound of the present invention may be used in personal care compositions, such as contact lens solution, used as adhesives, in the vulcanization of rubbers, used in polyurethane manufacturing processes, used in dye compositions, used as an ink composition, used as a dispersant in agricultural applications, such as a dispersant in an antifungal composition, among other compositions.
Formulations Table 1-Li u id Laundr Cleaninompositions C
A
Ingredients [% by wt.]
Linear 10-15 alkylbenzenesulfonate Clz_~s alcohol 1-5 ethoxy (1.l-2.5) sulfate Ciz-i3 alcohol 1-5 ethoxylate ~~_9~
cocodimethyl 0.1-1 amine oxide fatty acid 1-5 citric acid 1-5 Polymer c' 0.5-3 hydroxylated 5-20 castor oil (structurant) Vi~ater, perfumes,ad 100 dyes, and other trace components polymer according to any one of Examples 1-3 and formula I-IVof the present application.
Table 2 Low Sudsin ularundtCleaning Compositions Gran La B C D
Wt% Wt% wt%
C1,_,z Linear alkyl benzene 7 5.1 10.2 sul honate C~z-is tallow alk 1 1 1 1 sulfate C,4-is alk 1 ethox 3.2 3.2 3.2 late EO=7 APA~ 0.940,681.36 silicate builderz 4.05- -Zeolite A3 16.65- -Carbonate4 14.04- -Citric Acid Anh drous2.932.932.93 acrylic acid/maleic 0.97 acid 0.970.97 co of mers Pol mer6 1-5 1-5 1-5 Percarbonate 12.816.1813.25 tetraace leth lenediamine3.645.923.95 1-hydroxyethyidene-l , l - 0.180.180.18 di hos honic acid S,S-(ethylenediamine N,N'- 0.2 0.2 0.2 disuccinic acid) M S04 0.420.420.42 ENZYMES' % article 1.261.261.26 MINORS (perfume, Ad Ad Ad dyes, suds 100 100 100 stabilizers I Ca-so amido propyl dimethyl amine Z Amorphous Sodium Silicate (Si02:Na20; 2.0 ratio) 3 Hydrated Sodium Aluminosilicate of formula NaI2(A102Si02)12~ 27H20 having a primary particle size in the range from 0.1 to 10 micrometers 4Anhydrous sodium carbonate with a particle size between 200~m and 900~m 4:1 acrylic acid/maleic acid, average molecular weigh about 70,000 or 6:4 acrylic acid/maleic acid, average molecular weight about 10,000) ~ polymer accordin to any one of Examples I-3 or formula I-IV of the present invention ~ one or more enzymes such as:
Protease - Proteolytic enzyme, having 3.3% by weight of active enzyme, sold by NOVO Industries A/S
under the tradename SAVINASE~; Proteolytic enzyme, having 4% by weight of active enzyme, as described in WO 95/10591, sold by Genencor Int. Inc.
Alcalase- Proteolytic enzyme, having 5.3% by weight of active enzyme, sold by NOVO Industries A/S
Cellulase - Cellulytic enzyme, having 0.23% by weight of active enzyme, sold by NOVO Industries A/S
under the tradename CAREZYME~.
Amylase - Amylolytic enzyme, having 1.6% by weight of active enzyme, sold by NOVO Industries A/S
under the fradename TERMAMYL 120T~; Amylolytic enzyme, as disclosed in PCT/
US9703635.
Lipase - Lipolytic enzyme, having 2.0% by weight of active enzyme, sold by NOVO Industries A/S under the tradename LIPOLASE~; Lipolytic enzyme, having 2.0% by weight of active enzyme, sold by NOVO
Industries A/S under the tradename LIPOLASE ULTRA.
Endolase - Endoglucanase enzyme, having 1.5% by weight of active enzyme, sold by NOVO Industries A/S.
TableranularLaundCleaning Compositions G
E F G H
wt% wt% wt% wt%
Clo_,z linear 13.4- 15.2-alkyl 15.0 17.2 2.7 2.7 sul honate Csz-sa alkyl ethoxylate.8 .8 .0 .0 EO=9 Builders 18 -- -- --Se uestrantz-- 17 -- --enz me 0.35 0.40 -- --Pol mer3 1-2 1-2 1 1 Carboxy Methyl Cellulose.2 .2 .5 -suds su ressor40.01 0.01 -- --Pol ac 0.80 0.8 0.5 later buffer 4.0 2.0 6.0 6.0 Carbonate 11.0 15.0 8.0 8.0 bri htener0.08 0.08 0.03 0.03 Sodium 65.0 65.0 Sulfate 34.83 32.339 9 Water and Ad Ad Ad Ad minors 100 100 100 100 I sodium tripolyphosphate Zeolite A: Hydrated Sodium Aluminosilicate of formula Nal2(A102Si02)12~ 2~H20 having a primary particle size in the range from 0.1 to 10 micrometers 3. An modified alkoxylated polyol compound according to Examples 1-3 and formula I-IV of the present application 4. suds suppressor 5 Mw=4500 Table 4 Hard Surfa ce Cleanin Com ositions Moor cleaningfloor cleaning ipe solutionolution I J
Wt% wt%
C, I alcohol ethoxylate EO=5 0.03 0.03 Sodium C8 Sulfonate0.01 0.01 Propylene Glycol n-Butyl 2 2 Ether 2-Phenox ethanol 0.05 0.05 Ethanol 3 Pol mere 0.015 0.015 2-Dimethylamino-2-methyl-2- ro anol DMAMP 0.01 0.01 erfume 0.01-0.060.01-0.06 Suds su ressor2 0.003 0.003 2-methyl-4-isothaizolin-3 --one 0.015 + chloro derivative Water and minors Ad 100 Ad 100 ~
polymer according to Examples 1-3 and formula I-IVof the present application.
Z such as Dow Corning AF Emulsion or polydimethyl siloxane Table 5 Liauid Dishwashing Cleaning Composition K L M
C,z-,3 alcohol ethox late sulfate 26 23 24 EO=0.6 Amine Oxide 5.8 5.8 5.8 C8_,z alcohol ethox late EO=8 2 2 2 Ethanol 2 2 2 Sodium cumene sulfonate 1.80 1.80 1.80 NaCI 1,4 1.4 1.4 M Clz 0.2 0.2 0.2 Suds Booster' 0.2 0.2 0.2 Pol merz 0.8 0.8 0.8 Water & other trace components (i.e.,dye,ad ad ad perfume, 100 100 100 diamine, etc.
' as described in US 6,645,925 Bl 2 a polymer according to Examples 1- 3 and formula I-IVof the present invention.
All documents cited in the Detailed Description of the Invention are, are, in relevant part, incorporated herein by reference; the citation of any document is not to be construed as an admission that it is prior art with respect to the present invention.
While particular embodiments of the present invention have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.
Claims (10)
1. A compound characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties further comprise an anionic capping unit.
2. A compound characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties further comprises an anionic capping unit and at least one of the hydroxy moieties is substituted by an amine capping unit.
3. A compound characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties further comprises an anionic capping unit and at least one of the hydroxy moieties is substituted by a quaternary amine capping unit.
4. A compound characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy moieties, at least one of the hydroxy moieties further comprising a alkoxy moiety, the alkoxy moiety is selected from the group consisting of ethoxy, propoxy, butoxy and mixtures thereof; further wherein at least one of the hydroxy moieties further comprises an anionic capping unit, at least one of the hydroxy moieties is substituted by an amine capping unit and at least one of the hydroxy moieties is substituted by a quaternary amine capping unit.
5. The compound of Claim 1 wherein the hydroxy moieties comprise the alkoxy moiety comprising an average degree of alkoxylation per hydroxy moiety from 1 to 100.
6. The compound of any of Claims 1 to 5 wherein at least one of the anionic capping units is substituted by an amine capping unit.
7. The compound of any of Claims 2 or 4 wherein the amine capping unit is selected from the group consisting of ammonia, methyl amine, dimethylamine, ethylene diamine, dimethylaminopropylamine, bis dimethylaminopropylamine (bis DMAPA), hexemethylene diamine, ethylamine, diethylamine, dodecylamine, benzylamine, polyethylene imine, isoquinoline, tallow triethylenediamine, mono substituted monoarnine, monosubstituted diamine, monosubstituted polyamine, disubstituted monoamine, disubstiuted diamine, disubstituted polyamine, trisubstituted triamine, tri substituted polyamine, multisubstituted polyamine comprising more than three substitutions provided at least one nitrogen contains a hydrogen, and mixtures thereof.
8. The compound of any of Claims 1, 2, 3, or 4 wherein the polyol compound is derived from a sugar or reduced sugar monomers being selected from the group of glucose, maltose, maltotriose, maltopentose, maltohexose sorbitol, maltitol, sucrose, xylitol, glycerol, glycerol derivatives, polyglycerol, pentaerythitol, poly vinyl alcohol, xylan, reduced maltotriose, reduced maltodextrins, and mixtures thereof.
9. A cleaning composition comprising a compound characterized by comprising the compound according to any one of Claims 1, 2, 3, or 4.
10. The cleaning composition of Claim 18 wherein the cleaning composition further comprises a surfactant selected from anionic, nonionic, cationic, zwitterionic, amphoteric, and mixtures thereof.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US53138503P | 2003-12-19 | 2003-12-19 | |
US60/531,385 | 2003-12-19 | ||
PCT/US2004/043074 WO2005063847A1 (en) | 2003-12-19 | 2004-12-17 | Modified alkoxylated polyol compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2549571A1 true CA2549571A1 (en) | 2005-07-14 |
Family
ID=34738644
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002549571A Abandoned CA2549571A1 (en) | 2003-12-19 | 2004-12-17 | Modified alkoxylated polyol compounds |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP1694741A1 (en) |
JP (1) | JP2007520459A (en) |
CN (1) | CN1894305B (en) |
AR (1) | AR047292A1 (en) |
BR (1) | BRPI0417536A (en) |
CA (1) | CA2549571A1 (en) |
MX (1) | MXPA06007020A (en) |
WO (1) | WO2005063847A1 (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101084297A (en) | 2004-12-17 | 2007-12-05 | 宝洁公司 | Hydrophobically modified polyols for improved hydrophobic soil cleaning |
CA2589395A1 (en) * | 2004-12-17 | 2006-06-22 | The Procter & Gamble Company | Hydrophilically modified polyols for improved hydrophobic soil cleaning |
EP2029087A1 (en) | 2006-06-12 | 2009-03-04 | The Procter and Gamble Company | A lotioned wipe product comprising an anti-stick agent and a performance enhancing agent |
US9119779B2 (en) | 2006-06-12 | 2015-09-01 | The Procter & Gamble Company | Lotioned wipe product comprising an anti-stick agent and a performance enhancing agent |
US8093352B2 (en) | 2008-08-05 | 2012-01-10 | Alcon Research, Ltd. | Polyalkylene oxide polyquaternary ammonium biocides |
CN105732442B (en) * | 2016-01-27 | 2017-11-03 | 江苏苏博特新材料股份有限公司 | Oligomeric-type surfactant, its preparation method and application |
AU2021366966A1 (en) * | 2020-10-19 | 2023-03-02 | Oxiteno S.A. Indústria E Comércio | Composition, agrochemical formulation, methods for increasing water and nutrient availability and for improving pest control in plants and seeds, and uses of the composition and the agrochemical formulation |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS591784A (en) * | 1982-06-24 | 1984-01-07 | 東邦化学工業株式会社 | Dyeing aid for polyester fiber or polyester/cellulose fiber blended mixture |
NO165797C (en) * | 1985-01-03 | 1991-04-10 | Berol Kemi Ab | SURFACE ACTIVE COMPOUND AND EMULSION CONTAINING THIS, AND USE THEREOF. |
DE3633421C1 (en) * | 1986-10-01 | 1987-07-23 | Goldschmidt Ag Th | Polyoxyalkylene ethers containing hydroxyl and sulfonate groups and their use in the production of dispersible polyurethanes |
JPH06306041A (en) * | 1993-04-23 | 1994-11-01 | Kao Corp | Monoglyceride disulfate salt and production of monoglyceride sulfate containing the disulfate salt |
EP0638685B1 (en) * | 1993-08-10 | 1998-12-23 | Ciba SC Holding AG | Welling agent for mercerising |
US5650234A (en) * | 1994-09-09 | 1997-07-22 | Surface Engineering Technologies, Division Of Innerdyne, Inc. | Electrophilic polyethylene oxides for the modification of polysaccharides, polypeptides (proteins) and surfaces |
DE4441363A1 (en) * | 1994-11-21 | 1996-05-23 | Huels Chemische Werke Ag | Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on di, oligo or polyol ethers |
US5686603A (en) * | 1995-05-04 | 1997-11-11 | Lever Brothers Company, Division Of Conopco, Inc. | Sulfated polyhydroxy compounds as anionic surfactants and a process for their manufacture |
JPH09249636A (en) * | 1996-03-19 | 1997-09-22 | Kao Corp | Production of n-alkylamidoalkanol sulfuric acid ester salt |
JPH10279553A (en) * | 1997-04-03 | 1998-10-20 | Lion Corp | Production of (poly)glyceryl ether sulfate salt |
JP2001097942A (en) * | 1999-09-28 | 2001-04-10 | Kao Corp | Method for preparing monoglyceride sulfate |
JP4208462B2 (en) * | 2000-12-28 | 2009-01-14 | 株式会社Adeka | Surfactant |
US6602839B2 (en) * | 2001-01-05 | 2003-08-05 | Huntsman Petrochemical Corporation | Advanced sulfosuccinamate surfactants |
-
2004
- 2004-12-17 MX MXPA06007020A patent/MXPA06007020A/en active IP Right Grant
- 2004-12-17 CA CA002549571A patent/CA2549571A1/en not_active Abandoned
- 2004-12-17 AR ARP040104762 patent/AR047292A1/en unknown
- 2004-12-17 BR BRPI0417536-0A patent/BRPI0417536A/en not_active IP Right Cessation
- 2004-12-17 CN CN2004800378221A patent/CN1894305B/en not_active Expired - Fee Related
- 2004-12-17 WO PCT/US2004/043074 patent/WO2005063847A1/en not_active Application Discontinuation
- 2004-12-17 EP EP04815188A patent/EP1694741A1/en not_active Withdrawn
- 2004-12-17 JP JP2006544144A patent/JP2007520459A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
AR047292A1 (en) | 2006-01-11 |
CN1894305A (en) | 2007-01-10 |
CN1894305B (en) | 2010-10-13 |
WO2005063847A1 (en) | 2005-07-14 |
JP2007520459A (en) | 2007-07-26 |
BRPI0417536A (en) | 2007-03-27 |
EP1694741A1 (en) | 2006-08-30 |
MXPA06007020A (en) | 2006-08-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7550631B2 (en) | Modified alkoxylated polyol compounds | |
ES2355743T3 (en) | CLEANING COMPOSITIONS WITH ALCOXYLED POLYCHYLENIMINES. | |
CA2702824C (en) | Cleaning compositions with alkoxylated polyalkanolamines | |
US7332467B2 (en) | Hydrophilically modified polyols for improved hydrophobic soil cleaning | |
US20060135396A1 (en) | Hydrophobically modified polyols for improved hydrophobic soil cleaning | |
KR20150139887A (en) | Polyetheramines based on 1,3-dialcohols | |
EP3218465B1 (en) | Laundry detergents containing soil release polymers | |
US7468348B2 (en) | Alkoxylated polyol containing bleach activating terminating functional groups | |
US7439219B2 (en) | Modified alkoxylated polyol compounds | |
US20050153860A1 (en) | Hydrophobic polyamine ethoxylates | |
CA2549571A1 (en) | Modified alkoxylated polyol compounds | |
CN101460542B (en) | Detergent compositions | |
MXPA06008784A (en) | Alkoxylated polyol containing bleach activating terminating functional groups |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
FZDE | Discontinued |