MXPA06007020A - Modified alkoxylated polyol compounds. - Google Patents
Modified alkoxylated polyol compounds.Info
- Publication number
- MXPA06007020A MXPA06007020A MXPA06007020A MXPA06007020A MXPA06007020A MX PA06007020 A MXPA06007020 A MX PA06007020A MX PA06007020 A MXPA06007020 A MX PA06007020A MX PA06007020 A MXPA06007020 A MX PA06007020A MX PA06007020 A MXPA06007020 A MX PA06007020A
- Authority
- MX
- Mexico
- Prior art keywords
- coronation
- unit
- hydroxy
- anionic
- amine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 40
- 229920005628 alkoxylated polyol Polymers 0.000 title description 32
- 239000000203 mixture Substances 0.000 claims abstract description 143
- 238000004140 cleaning Methods 0.000 claims abstract description 81
- -1 polyol compound Chemical class 0.000 claims abstract description 59
- 229920005862 polyol Polymers 0.000 claims abstract description 53
- 125000000129 anionic group Chemical group 0.000 claims abstract description 51
- 150000001412 amines Chemical class 0.000 claims description 39
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 150000003077 polyols Chemical class 0.000 claims description 28
- 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 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 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 14
- 239000000600 sorbitol Substances 0.000 claims description 14
- 229920000768 polyamine Polymers 0.000 claims description 13
- 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
- 150000004985 diamines Chemical class 0.000 claims description 8
- 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
- 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
- 239000000845 maltitol Substances 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
- 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
- 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 4
- 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 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-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
- 125000002091 cationic group Chemical group 0.000 claims description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-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
- 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 4
- 238000006467 substitution reaction Methods 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
- 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 4
- 229920002774 Maltodextrin Polymers 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 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
- 239000003760 tallow Substances 0.000 claims description 2
- 239000000811 xylitol Substances 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
- 235000010447 xylitol Nutrition 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
- 239000002280 amphoteric surfactant Substances 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 45
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- 239000004094 surface-active agent Substances 0.000 description 22
- 230000008569 process Effects 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000004851 dishwashing Methods 0.000 description 15
- 239000004744 fabric Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 230000004048 modification Effects 0.000 description 9
- 238000012986 modification Methods 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 229910019142 PO4 Inorganic materials 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000003599 detergent Substances 0.000 description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
- 235000021317 phosphate Nutrition 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 239000003945 anionic surfactant Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 7
- 239000010452 phosphate Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 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
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000002736 nonionic surfactant Substances 0.000 description 6
- 238000005956 quaternization reaction Methods 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 230000036961 partial effect Effects 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 108091005804 Peptidases Proteins 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000008051 alkyl sulfates Chemical class 0.000 description 4
- 239000007844 bleaching agent Substances 0.000 description 4
- 239000002270 dispersing agent 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
- 238000001208 nuclear magnetic resonance pulse sequence Methods 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
- 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- 239000003637 basic solution Substances 0.000 description 3
- 229960003237 betaine Drugs 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000011538 cleaning material Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000839 emulsion Substances 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
- 238000010348 incorporation Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000002563 ionic surfactant Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920001451 polypropylene glycol Polymers 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 class 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- 239000002888 zwitterionic surfactant Substances 0.000 description 3
- RGHNJXZEOKUKBD-NRXMZTRTSA-N (2r,3r,4r,5s)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-NRXMZTRTSA-N 0.000 description 2
- 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229910000503 Na-aluminosilicate Inorganic materials 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004614 Process Aid Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 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
- 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
- 239000000919 ceramic Substances 0.000 description 2
- 239000003086 colorant Substances 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
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- 239000003752 hydrotrope Substances 0.000 description 2
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- 230000002366 lipolytic effect Effects 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
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- 229920000570 polyether 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
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 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
- 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
- 238000003756 stirring Methods 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
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000004073 vulcanization Methods 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
- 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
- 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
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-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
- 201000004002 Aromatase excess syndrome Diseases 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- 208000035484 Cellulite Diseases 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-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
- 206010049752 Peau d'orange Diseases 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
- 239000004772 Sontara Substances 0.000 description 1
- 108010056079 Subtilisins Proteins 0.000 description 1
- 102000005158 Subtilisins Human genes 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000996 additive effect Effects 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
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 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
- 229910052786 argon Inorganic materials 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
- 239000002585 base Substances 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
- 238000004061 bleaching Methods 0.000 description 1
- 229910052796 boron Inorganic materials 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
- 125000005587 carbonate group Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 230000036232 cellulite Effects 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
- 239000004927 clay Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000000882 contact lens solution Substances 0.000 description 1
- 239000000109 continuous material Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 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
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical class OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002070 germicidal effect Effects 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
- 238000010438 heat treatment Methods 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
- 238000005470 impregnation Methods 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
- 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
- 238000003760 magnetic stirring Methods 0.000 description 1
- 229940035034 maltodextrin Drugs 0.000 description 1
- 238000010907 mechanical stirring Methods 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
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 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
- 239000002304 perfume 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
- 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
- 230000005588 protonation Effects 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
- 230000009467 reduction Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 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
- 238000001228 spectrum Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 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
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 239000010457 zeolite Substances 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
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- 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)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Detergent Compositions (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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 ALCOXYLENE POLYOL COMPOUNDS
FIELD OF THE INVENTION
This invention relates to modified alkoxylated polyol compounds, methods for making modified alkoxylated polyol compounds, and cleaning compositions comprising the same.
BACKGROUND OF THE INVENTION
Polyol compounds such as sugars such as sucrose or maltitoise are known as sustainable and readily available raw materials. The maltitol ethoxylates, e.g. ex. CAS 503446-80-8. This material has been widely disclosed as a surfactant for cosmetics and other personal care applications as described in JP 2003-096182. Other known ethoxylated polyols include: ethoxylated mannitol (CAS 53047-01-2), ethoxylated inostol (CAS 503446-79-5), ethoxylated sorbitol (CAS 53694-15-8). JP 10-081744 discusses the production of polyether polyols by the addition of alkylene oxides to a saccharide in the presence of amine catalysts. However, as the term "catalyst" implies, the amine catalysts are not incorporated into the structure of the polyether polyol.
Also known are the series of amine-terminated ethoxylates known in the industry as JEFFAMINES® and marketed by Huntsman. These are derived mainly from polyethylene glycol and mixtures of polyethylene glycol and polypropylene glycol wherein the glycols are directly amined with ammonia and a catalyst. These are called the JEFFAMINE D® and JEFFAMINE ED® series. The most complex mixture of the JEFFAMINES® series is the T series. The JEFFAMINES® are based on trimethylolpropane or glycerin and thus have three finished ethoxy / propoxy strands of ammonia that radiate from the glycerin or trimethylolpropane core. The amination of the polyols with ammonia and other amines is further illustrated in U.S. Pat. no. 5,371, 119, but uses the modification of the polyol specifically via the epichlorohydrin to form a polyol bis-halohydrin followed by reaction with ammonia or an amine to form the repeating network of amino polyols. This results in the formation of a complex polymerized mixture containing multiple polyols randomly linked via the reactive halohydrin. This complex mixture is not considered of value to formulators of cleaning compositions for the purpose of providing cleaning benefits and is aimed at forming emulsifiers. The simple amination of the polyols is described in the WO patent
01/98388 A, which discusses simple animated polyols, further reacted with aldehydes, in particular formaldehyde, to make complex polymer networks. Included in these complex structures is the ability to have the sulfide, the carboxylate, the alkyl esters, the alkylsulfonates, and the alkyl phosphates as a functional unit of the complex structure. However, the resulting complex polymer networks are not considered of value to formulators of cleaning compositions for the purpose of providing cleaning benefits. In addition, it has not been taught to manipulate these materials in a controlled and specific manner. Selective modification of sugar derived polyols to highly provide modified polyols is highly desirable where the star-like structure is refined to meet the needs of detergent formulators. There is also a need for materials that are relatively easy to manufacture from readily available and sustainable raw materials, which can be adjusted in general terms to address specific performance requirements. Tension conditions also present the additional problem that anionic surfactants such as alkylbenzene sulphonates or linear alkyl sulphates form higher order aggregates. The aggregation of the anionic surfactant reduces the amount of the anionic surfactant available for cleaning. There is a need for materials that are relatively easy to manufacture from sustainable and readily available raw materials, which can be refined in a controlled and specific way to deal with specific formulation and performance requirements. A multifunctional cleaning material is desired that provides greater availability of the surfactant, avoiding the formation of higher order aggregates of the anionic surfactant with water free of hardness during use. Specific performance requirements include providing hydrophobic spot cleaning (grease, oil) to hydrophilic (clay) spots associated with dirty exteriors. Other performance requirements include uses in personal care compositions such as solutions for contact lenses, uses in adhesives, vulcanization of rubbers, use in polyurethane processes, use as colorant additives, alfalto dispersants, dissolution aids of the surfactant, the use in solubilizers of surfactants in the presence of calcium and magnesium, among other performance requirements. The formulation of some current commercial polymers, which provide for the cleaning of dirty exteriors, in granular detergents and laundry liquids, hard surface cleaners, dishwashing compositions, personal care compositions, as well as well drilling compositions tankers, continues to challenge detergent formulators.
BRIEF DESCRIPTION OF THE INVENTION
The present invention relates to compounds, processes, cleaning compositions, and methods for using said compounds and compositions, characterized in that they comprise a polyol compound; the polyol compound comprises at least three hydroxy portions, at least one of the hydroxy portions further comprises an alkoxy portion, the alkoxy portion is selected from the group comprising ethoxy, propoxy, butoxy and mixtures thereof; wherein also at least one of the hydroxy portions comprises an anionic coronation unit. The present invention further relates to compounds, processes, cleaning compositions, and methods for using said compounds and compositions characterized by comprising a polyol compound, the polyol compound comprising at least three hydroxy portions, at least one of the hydroxy portions further comprising an alkoxy moiety, the alkoxy moiety is selected from the group comprising ethoxy, propoxy, butoxy and mixtures thereof; wherein in addition at least one of the hydroxy portions is replaced by and thus further comprises an anionic coronation unit and at least one of the hydroxy portions is replaced by an amine coronation unit. The present invention further relates to compounds, processes, cleaning compositions, and methods for using said compounds and compositions characterized by comprising a polyol compound; the polyol compound comprises at least three hydroxy portions, at least one of the hydroxy portions further comprises an alkoxy portion, the alkoxy portion is selected from the group comprising ethoxy, propoxy, butoxy and mixtures thereof; wherein in addition at least one of the hydroxy portions is replaced by and thereby comprises an anionic coronation unit and at least one of the hydroxy portions is replaced by a quaternary amine coronation unit. The present invention further relates to compounds, processes, cleaning compositions, and methods for using said compounds and compositions characterized by comprising a polyol compound; the polyol compound comprises at least three hydroxy portions, at least one of the hydroxy portions further comprises an alkoxy portion, the alkoxy portion is selected from the group comprising ethoxy, propoxy, butoxy and mixtures thereof; wherein in addition at least one of the hydroxy portions is replaced by and thereby comprises an anionic coronation unit.
DETAILED DESCRIPTION OF THE INVENTION
Materials that are relatively easy to manufacture from sustainable and readily available raw materials are needed, which can be extensively tuned to address specific formulation and performance requirements. Polyol compounds such as sugar-based materials and polyethylene glycol / propylene glycol materials are sustainable and readily available raw materials that lend themselves to being extensively refined to address specific formulation and performance requirements. As used herein, "tuning" means having the ability to manipulate the chemical structure of the polyol compounds to achieve a characteristic chemical functionality. For example, a modified alkoxylated polyol compound to include an anionic coronation unit is a fine-tuned structure that provides desired characteristics for specific formulation and performance requirements. As another example, an alkoxylated polyol compound modified to include an anionic coronation unit and an amine coronation unit is a fine-tuned structure that provides desired characteristics. Another example is when an alkoxylated polyol compound is modified by comprising an anionic coronation unit and a quaternary amine coronation unit, it is a refined structure that provides the desired characteristics. Finally, another example may contain both elements of the two examples, thus containing an anionic coronation unit and an amine and a quaternary amine coronation unit. The polyol compounds useful in the present invention comprise at least three hydroxy portions, preferably more than three hydroxy portions, more preferably six or more hydroxy portions. At least one of the hydroxy portions further comprises an alkoxy moiety; the alkoxy portion is selected from the group comprising ethoxy (EO), 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. The alkoxylation is preferably a block alkoxylation. The polyol compounds useful in the present invention also have at least one of the alkoxy moieties comprising at least one anionic coronation unit. Other modifications or refinement of the compound may occur, but an amine coronation unit must be present in the compound of the present invention. An embodiment comprises more than one hydroxy portion further comprising an alkoxy portion having an anionic coronation unit. For example Formula (I): Formula (I)
wherein x of formula (I) is about 1 to about 100, or about 10 to about 40. Anionic Units crowning suitable include sulfate, sulfosuccinate, succinate, maleate, phosphate, phthalate, sulfocarboxilato, sulfodicarboxilato, propane sultone, 1 , 2-disulfopropanol, sulfopropilamina, sulphonate, monocarboxylate, carboxylate methylene carboxylate, ethylene carbonate, melifico acid, pyromellitic acid, sulfophenol, sulfocatecol, disulfocatecol, tartrate, citrate, acrylate, methacrylate, polyacrylate copolymer, polyacrylate-maleate, and mixtures of these. Preferably the anionic coronation units are sulfate, sulfosuccinate, succinate, maleate, sulfonate, methylene carboxylate and ethylene carboxylate. Compounds suitable polyol for raw materials to be used in the present invention maltitol, include sucrose, xylitol, glycerol, pentaerotriol, glucose, maltose, maltotriose, maltodextrin, maltopentose, maltohexose, isomaltulose, sorbitol, polyvinyl alcohol, partially hydrolyzed polyvinylacetate, maltotriose reduced with xylan, reduced maltodextrins, polyethylene glycol, polypropylene glycol, polyglycerol, diglycerol ether and mixtures thereof. Suitable examples include the polyol compound which is chosen from 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. The refinement of the polyol compounds can be derived from one or more modifications, depending on the desired formulation and performance requirements. Tuning requires anionic modifications and may include the incorporation of cationic or zwitterionic charge modifications to the polyol compounds. In one embodiment of the present invention, at least one hydroxy moiety includes an alkoxy moiety, wherein the alkoxy moiety further includes at least one anionic coronation unit. In another embodiment of the present invention, at least one hydroxy moiety includes an alkoxy moiety, wherein the alkoxy moiety further includes more than one anionic coronation unit, wherein at least one anionic coronation unit, but less than all of the Anionic coronation units are then selectively replaced by an amine coronation unit. The amine coronation unit is selected from a coronation unit containing a primary amine, a coronation unit containing a secondary amine, a coronation unit containing a tertiary amine, and mixtures thereof. Suitable primary amines for the coronation unit containing a primary amine include monoamines, diamine, triamine, polyamines, and mixtures thereof. Suitable secondary amines for the coronation unit containing a secondary amine include monoamines, diamine, triamine, polyamines, and mixtures thereof. Suitable tertiary amines for the coronation unit containing a tertiary amine include monoamines, diamine, triamine, polyamines, and mixtures thereof. Monoamines, diamines, triamines or polyamines suitable for use in the present invention include ammonia, methylamine, dimethylamine, ethylenediamine, dimethylaminopropylamine, dimethylaminopropylamine bis (bis DMAPA), hexamethylene diamine, benzylamine, isoquinoline, ethylamine, diethylamine, dodecylamine, triethylenediamine tallow monoamine mono-substituted, monosubstituted diamine, monosubstituted polyamine, disubstituted monoamine, diamine disubstituted polyamine disubstituted triamine tri-substituted, tri-substituted polyamine, polyamine-substituted multi comprising more than three substitutions provided by at least one nitrogen contains a hydrogen, and mixtures of these. In another embodiment of the present invention, at least one of the nitrogens in the amine coronation unit is quaternized. As used herein, "quaternized" means that the amine coronation unit is given a positive charge through quaternization or protonation of the amine coronation unit. For example, bis-DMAPA contains three nitrogens; only one of the nitrogens needs to be quaternized. However, it is preferred to have all the quaternized nitrogens in a given amine coronation unit.
The refinement or modification can be combined depending on the desired formulation and performance requirements. Non-exhaustive examples of modified polyol compounds of the present invention include:
Formula (II)
wherein x of Formula (I) is from about 1 to about 100; and such as from about 10 to about 40.
Formula (III)
Formula (IV) Production Process The present invention also relates to a process for 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 portions, such that the average degree of alkoxylation of at least one hydroxy portion is from about 1 to about 100; preferably from about 4 to about 60; more preferably 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 polyoxyethylene sorbitol ether available from Lipo Chemicals Inc., may be used as the raw material of the present invention. If the average degree of alkoxylation is not a desired level, an alkoxylation step can be used to obtain the desired degree of alkoxylation of from about 1 to about 100, preferably from about 4 to about 60; Then, the process comprises the step of reacting at least one alkoxy portion of the compound with an anionic coronation unit to form an anionic alkoxylated polyol, although more anionic coronation units may be chosen. In one embodiment the process comprises another step of replacing at least one anionic coronation unit of the anionic alkoxylated polyol with an amine coronation unit to form an alkoxylated anionic aminated polyol. In this process only certain anionic coronation units can 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 coronation of the anionic alkoxylated alkoxylated polyol to form a zwitterionic alkoxylated polyol. The quaternization can be carried out in any of the anionic alkoxylated aminated polyols. In one embodiment, the process comprises the step of alkoxylating some or most of the hydroxy portions of the polyol, so that the 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, to form an alkoxylated polyol. The process further includes the step of reacting the alkoxy portion of the alkoxylated polyol with at least one anionic coronation unit containing at least one of the following anionic groups: sulfate, phosphate and carbonate to form an anionic alkoxylated polyol. The process can partially or completely react the alkoxy portion of the alkoxylated polyol with an anionic coronation unit. It is understood that anionic coronation units other than sulfate, phosphate or carbonate may also be present in the anionic alkoxylated polyol. Preferably all the alkoxy portions comprise an anionic coronation unit. Optionally, the process comprises the step of substituting the anionic coronation unit with an amine coronation unit chosen from sulfate, phosphate, and carbonate, and mixtures thereof, to form an alkoxylated aminated alkoxylated polyol (Scheme I below). The replacement of the anionic coronation units present with an amine coronation unit can be partial or total. Preferably the replacement of the anionic coronation unit with the amine coronation unit is partial to form an alkoxylated anionic aminated polyol. Optionally, the process also comprises the process of providing an aminated alkoxylated polyol by direct amination of the alkoxylated polyol using the catalytic amination (Scheme II below) Optionally, the process may further comprise the step of quatemizing at least one of the nitrogens of the amine coronation unit of the anionic alkoxylated polyol forming a zwitterionic alkoxylated polyol. The quaternization of the amine coronation unit of the anionic alkoxylated polyol can be partial or total. In one embodiment, the quaternization is partial. In another embodiment, the quatemization is total. The quatemization of the nitrogens of the amine coronation unit may be partial or total, preferably total. A non-exhaustive synthesis scheme is exemplified in Synthesis Scheme I and Synthesis Scheme II below: Synthesis Scheme I of the anionic aminated alkoxylated polyol
ro OO Pi The process may optionally comprise step 1, step 2, and optionally, steps 3 and 4. The step of providing the alkoxylated anionic aminated polyol by way of nucleophilic substitution of sulfate moieties by a unit of coronation of amine. This is a non-exhaustive example since phosphate or carbonate groups can also be used for substitution by an amine coronation unit. Synthesis scheme II:
+ 9 CH3OS03Na
+ 9 CH3OS03Na
Scheme II differs from Scheme I in two areas; (1) direct substitution of terminal hydroxy portions is obtained by catalytic oxidation / reduction using metal catalysts and hydrogen; (2) Sulfation is carried out after the amination and quaternization by transulfation as described in U.S. Pat. no. 6,452,035. A zwitterionic alkoxylated polyol of the same composition can be prepared by either Scheme I or Scheme II mentioned above. A person with experience in the industry will recognize that other amine coronation 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 the polyol The ethoxylation of the polyol such as sorbitol can be completed by any known technique, such as that described in EP 174436 A1. Propoxylation and butoxylation can also be completed by known techniques. Sorbitol (17.5 g, 0.0962 mol) is added to an autoclave, purge the autoclave with nitrogen, heat the sorbitol at 110-120 ° C; shake the autoclave and apply vacuum at approximately 2.6 kPa (20 mmHg.) The vacuum is applied continuously while the autoclave is cooled to approximately 110-120 ° C. While introducing 6.2 g of a sodium methoxide solution in 25% methanol (0.0288 mol, to obtain a catalyst load of 5% based on the hydroxy portions). The methanol is removed from the methoxide solution of the autoclave under vacuum. A device is used to monitor the energy consumption by the agitator. The energy of the agitator is monitored along with the temperature and pressure. The agitator energy values and temperature are gradually increased as the methanol is removed from the autoclave and the viscosity of the mixture is increased and stabilized at about 1.5 hours indicating that most of the methanol has been removed. The mixture is heated further and stirred under vacuum for an additional 30 minutes. The vacuum is removed and the autoclave is cooled or maintained
110 ° C while being loaded with nitrogen at 1725 kPa (250 psia) and then discharged at ambient pressure. The autoclave is charged at 1380 kPa (200 psia) with nitrogen. Ethylene oxide is added to the autoclave incrementally while closely monitoring the autoclave pressure, temperature, and flow velocity of ethylene oxide while maintaining the temperature between 110 and 120 ° C. Limiting any increase in temperature due to exothermic reaction. After the addition of 483 g of ethylene oxide (10.97 mol, resulting in a total of 19 mol of ethylene oxide per mol of OH), the temperature is increased to 120 ° C. The mixture is stirred for an additional 2 hours. Then, the reaction mixture is collected in a 22 L three-necked round bottom flask purged with nitrogen. The strong alkaline catalyst is neutralized by the slow addition of 2.8 g of methanesulfonic acid (0.00288 mol) with heating (110 ° C.) And mechanical stirring. The residual ethylene oxide reaction mixture is then purged and deodorized by spreading an inert gas (argon or nitrogen) into the mixture through a gas dispersion frit while the mixture is stirred and heated at 120 ° C for 1 hour. The final reaction product, approximately 500 g, cooled slightly, and poured into a glass container purged with nitrogen for storage. Alternatively, the polyol can be purchased with a degree of alkoxylation that is below that desired, such as CAS 52625-13-5, a propoxylated sorbitol or a polyoxyethylene sorbitol ether available from Lipo Chemicals Inc. Where the desired degree of alkoxylation it is obtained by processes known and / or described above. Sulfation of sorbitol EO- an average of 19 portions of EO per hydroxy portion) Weigh into a 500 mL Erlenmeyer flask sorbitol In
(299.7 g, 0.058 mol) and methylene chloride (300 g) ("the solution"). A magnetic stirring bar is installed in the flask and stirred until the dissolution is complete. The flask is placed in an ice bath until the solution reaches approximately 10 ° C. Stir vigorously while pouring chlorosulfonic acid (48.3 g, 0.415 mol) slowly over a period of about 5 minutes to form a reaction solution. The reaction solution is stirred in the ice bath for 1.5 hours.
Place a solution of sodium methoxide (197 g of 25% in methanol) in 50 g of methylene chloride in a 1 L Erlenmeyer flask ("basic solution") and cool in an ice bath until the temperature of the solution reaches approximately 10 ° C. The basic solution is stirred vigorously using a magnetic stir bar. The reaction solution is slowly poured into the basic solution over a period of about 3 minutes. A slight exothermic should be observed. The resulting solution becomes milky as salts are formed. After the addition, the pH is measured at approximately 12. To this resulting solution is added approximately 100 mL of distilled water, and the resulting emulsion is transferred to a 1 L round bottom flask and a rotary evaporator is used at 50 ° C. to clean, in portions, to obtain a clear solution. The clear solution is transferred to a Kulgelrohr apparatus. At 60 ° C and 133 Pa (1 mm Hg) the solution is cleaned to yield 66 g of a whitish, 90% active waxy solid (10% salts). The carbon NMR spectrum (500 MHz, pulse sequence: s2pu1, solvent D2O, relax, delay 0.300 s, pulse 45.0, acquisition time 1090 s) shows an absence of alcohol groups at approximately 60 ppm and the appearance of a new peak at approximately 67 ppm consistent with the formation of the final sulfate group. The proton NMR spectrum (500 MHz or 300 MHz, pulse sequence: s2pu1, solvent D2O, relax, delay 1,000 s, pulse 45.0, acquisition time 2,345 sec) shows a new peak at approximately 4 ppm, which was integrated with the protons of the ethoxy group at approximately 3.5 ppm, and is consistent with the molecule having 6 final group sulphates. Example 2: Amination of sorbitol EOI H hexasulfate of Example 1 Weigh within a 200 mL glass liner EOn4 sorbitol hexasulfate (61.3 g of 90% active, 0.0095 mol) and 3- (dimethylamino) propylamine ("DMAPA" 18.5 g) , 0.181 mol). The liner is heated in an oscillating autoclave at 152 kPa (150 psig) under nitrogen until the temperature reaches 165 ° C and is maintained at 165 ° C for 2 hours. It is cooled to room temperature (20-25 ° C). The material is taken up in 150 mL of methylene chloride and centrifuged to separate the salts. Transfer the supernatant to a 500 mL round bottom flask and remove the supernatant in a rotary evaporator at 50 ° C until most of the solvent is removed (less than 5 mL). It is heated in a Kugelrohr apparatus at 120 ° C and 133 Pa (1 mm Hg) for 30 minutes to remove the excess amine to produce 47.8 g of a hard brown solid. The proton NMR spectrum (500 MHz or 300 MHz, pulse sequence: s2pu1, solvent D2O, relax, delay 0.300 s, pulse 45.0, acquisition time 3744 s) resulted in approximately 3 sulfates and approximately 2 DMAPA per molecule. Example 3: Quaternization of the Amine-Containing Sulfate of Example 2 An amine sorbitol EOn4 is dissolved in 100 g of methylene chloride in a 500 mL round bottom flask equipped with a mechanical stir bar and cooled in an ice bath until the temperature reaches 10 ° C. The solution is adjusted to pH 12 with sodium methoxide (25% solution in methanol). Methyl iodide (15.0 g, 0.106 mol) is added to the solution. The flask is capped and the solution is stirred overnight (approximately 14 hours). The solution is purified in the Kugelrohr apparatus at 50 ° C and 133 Pa (1 mm Hg) to yield 66 g of a sticky brown solid. The proton NMR spectrum (500 MHz or 300 MHz; pulse sequence: s2pu1, solvent D2O; relax. Delay 1,000 s, pulse 45.0; acquisition time 2345 s) resulted in all nitrogens in the amine coronation unit being completely quaternized. Cleaning 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, bags, stick, gel, of the type that are supplied in double-compartment containers, atomized detergents or in foam, pre-moistened wipes (ie the cleaning composition in combination with a non-woven material such as that discussed in U.S. Patent No. 6,121, 165, Mackey, et al.), dry wipes ( that is, the cleaning composition in combination with nonwoven materials as discussed in U.S. Patent No. 5,980,931, Fowler, et al.), activated with water by a consumer, and other homogeneous or multiple forms. phases of consumer cleaning products.
In addition to the cleaning compositions, the compounds of the present invention may also be suitable for use or incorporation into industrial cleaners (ie floor cleaners). Sometimes these cleaning compositions will also comprise surfactants and other additive ingredients for cleaning, 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, "impregnation" means that the hard surface cleaning composition is placed in contact with a nonwoven substrate so 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 dishwashing composition such as liquid dishwashing compositions, solid dishwashing compositions in an automatic washing machine, liquid dishwashing compositions in an automatic washing machine, and tablet forms. / units of dishwashing compositions in automatic washing machine. The cleaning composition can also be used in automotive care compositions, to clean various surfaces such as hardwood, tile, ceramic, plastic, leather, metal, glass. This cleaning composition could also be designed to be used in a personal care composition such as shampoo composition, body wash composition, liquid or solid soap and other cleaning compositions in which the surfactant comes into contact with the free hardness of the water and in all compositions that require water hardness tolerant surfactant systems such as oil drilling compositions. Modified Alkoxylated Polyol Compounds The cleaning composition of the present invention may comprise from about 0.005% to about 30%, and from about 0.01% to about 10%, in addition to 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 a surfactant system comprising surfactants chosen from nonionic, anionic, cationic, ampholytic, zwitterionic, semi-polar nonionic surfactants, and other auxiliaries such as alkyl alcohols, or mixtures thereof. The cleaning composition of the present invention further includes from about 0.01% to about 90%, and from about 0.01% to about 80%, in addition to about 0.05% to about 50%, in addition to about 0.05% to about 40% by weight of the cleaning composition of a surfactant system having one or more surfactants. Anionic Surfactants: Non-exhaustive examples of anionic surfactants useful herein include: C8-C-? 8 alkylbenzene sulfonates (LAS); alkyl sulfates (AS)
Primary C-C20, branched-chain and random; C? 0-C18 secondary alkyl sulfates (2.3); C10-C? 8 alkylalkoxy sulfates (AEXS) wherein x is 1-30; alkylalkoxycarboxylates do-C-iß comprising 1-5 ethoxy units; branched chain alkyl sulfates as described in U.S. Pat. no. 6,020,303 and U.S. Pat. no. 6,060,443; branched chain alkylalkoxy sulfates as described in U.S. Pat. no. 6,008,181 and U.S. Pat. no.
6,020,303; modified alkylbenzene sulfonate (MLAS) as described 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: C12-C18 alkyl ethoxylates, such as NEODOL® nonionic surfactants from
Shell; C6-C12 alkylphenol alkoxylates wherein the alkoxylate units are a mixture of ethyleneoxy and propyleneoxy units; C-? 2-C18 alcohol and C6-C? 2 alkylphenol condensates with alkyl polyamine ethoxylates of ethylene oxide / propylene oxide blocks as PLURONIC® from BASF; branched middle chain (B-C) 4 4-C22 alcohols (BA) as described in U.S. Pat. no. 6,150,322; C14-C22 branched chain alkyl alkoxylates, BAEX, wherein x is 1-30, as described in U.S. Pat. no. 6,153,577, U.S. Pat. no. 6,020,303 and the US. no. 6,093,856; alkylpolysaccharides as described in U.S. Pat. no. 4,565,647 Filling, granted on January 26, 1986; specifically the alkylpolysaccharides as described in U.S. Pat. no. 4,483,780 and U.S. Pat. no. 4,483,779; fatty acid polyhydroxyamides (GS-base) as described in U.S. Pat. no. 5,332,528; and poly (oxyalkylated) alcohol surfactants with ether cap as described in U.S. Pat. no. 6,482,994 and WO 01/42408. Cationic Surfactants Non-limiting examples of anionic surfactants include quaternary ammonium surfactants, which may have up to 26 carbon atoms and include quaternary ammonium alkoxylate surfactants (AQA) as described in U.S. Pat. no. 6,136,769; quaternary ammonium dimethyl hydroxyethyl as described in patent no. 6,004,922; cationic polyamine surfactants described in patents WO 98/35002, WO 98/35003, WO 98/35004, WO 98/35005, and WO 98/35006; cationic ester surfactants as described in U.S. Pat. num. 4,228,042, 4,239,660 4,260,529 and 6,022,844; and aminosurfactants as described in U.S. Pat. no. 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 US Pat. no. 3,929,678 to Laughiin et al., Issued December 30,
1975 in column 19, line 38 to column 22, line 48, for examples of zwitterionic surfactants; betaine, including alkyl dimethyl betaine and cocodimethyl amidopropyl betaine, C8 to C? 8 (C 2 to C? 8) amine and sulfo oxides and hydroxy betaines such as N-alkyl-N, N-dimethylamino-1-propanesulfonate where the group alkyl can be C8 to C18, C 0 to C? 4. Ampholytic Surfactants Non-limiting examples of ampholytic surfactants include the aliphatic derivatives of secondary or tertiary amines, or the 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, usually from about 8 to about 18 carbon atoms, and at least one contains an anionic water-solubilizing group, e.g. ex. carboxy, sulfonate, sulfate. See column 19, lines 18-35 of U.S. Pat. no. 3,929,678 issued to Laughiin et al. on December 30, 1975, for examples of ampholytic surfactants.
Semi-polar nonionic surfactants Non-limiting examples of semi-polar nonionic surfactants include: water-soluble amine oxides containing an alkyl portion of about 10 to about 18 carbon atoms and 2 selected portions of the group comprising alkyl groups and hydroxyalkyl groups containing about 1 to about 3 carbon atoms; water-soluble phosphine oxides containing an alkyl portion of about 10 to about 18 carbon atoms and 2 selected portions of the group comprising alkyl groups and hydroxyalkyl groups containing from about 1 to about 3 carbon atoms; and water soluble sulfoxides containing an alkyl portion of about 10 to about 18 carbon atoms and a selected portion of the group comprising alkyl and hydroxyalkyl portions of about 1 to about 3 carbon atoms. See WO 01/32816, U.S. Pat. no.
4,681, 704, and U.S. Pat. no. 4,133,779. Qemini Surfactants Gemini surfactants are compounds that have at least two hydrophobic groups and at least two hydrophilic groups per molecule have been introduced. These are known as "gemini surfactants" in the literature, p. ex. Chemtech, March 1993, p. 30-33, and J. American Chemical
Soc, 115, 10083-10090 (1993) and the references cited therein.
Auxiliary Cleaning Materials In general, an auxiliary product is any material required to transform a cleaning composition containing only the minimum essential ingredients into a useful cleaning composition for laundry, hard surfaces, personal care, and for consumer cleaning purposes. , commercial and / or industrial. In certain embodiments, cleaning aids are readily recognized by those with industry experience as absolutely characteristic of cleaning products intended for direct use by a consumer in a domestic environment. The exact nature of these additional components, and the levels of incorporation thereof, will depend on the physical form of the cleaning composition and the nature of the cleaning operation for which it will be used. Auxiliary cleaning ingredients, if used with bleach, should have good stability with it. Certain embodiments of the cleaning compositions herein must be free of boron and / or free of phosphate as required by law. The levels of cleaning aids are from about 0.00001% to about 99.9%, and from about 0.0001% to about 50% by weight of the cleaning compositions. The total levels of use of the cleaning compositions can vary widely depending on the proposed application, varying for example from a few ppm in solution to the so-called "direct application" of the pure cleaning composition to the surface to be cleaned. Very typically, the cleaning compositions herein, such as laundry detergents, laundry detergent additives, hard surface cleaners, synthetic and soap based laundry bars, fabric softeners and liquids and solids for the treatment of fabrics, and treatment items of all kinds, will require several auxiliaries; although certain simply formulated products, such as bleaching additives, may only require, for example, an oxygen bleaching agent and a surfactant as described herein. A complete list of auxiliary laundry or cleaning materials can be found in WO 99/05242. Common cleaning aids include builders, enzymes, polymers not discussed above, bleach, bleach activators, catalytic materials and the like, excluding any material previously defined. Other cleaning aids herein may include foam enhancers, foam suppressors (antifoams) and the like, various active ingredients or specialized materials such as dispersing polymers (eg from BASF Corp. or Rohm &Haas). different from those described above, colored dots, agents for the care of the silverware, anti-stain and / or anti-corrosion agents, dyes, fillers, germicides, alkalinity sources, hydrotropes, antioxidants, enzyme stabilizing agents, properfumes, perfumes, solubilizing agents, carriers, process aids, pigments, and for liquid formulations, solvents, chelating agents, dye transfer inhibiting agents, dispersants, brighteners, foam suppressants, dyes, structure-elasticizing agents, fabric softeners, anti-abrasion agents, hydrotropes, process aids, and other agents for the care of the fabric and age for skin care. Suitable examples of these other cleaning aids and levels of use are found in U.S. Pat. num. 5, 576,282, 6,306,812 B1 and 6,326,348 B1. METHOD OF USE The present invention includes a method for cleaning a surface or fabric. This 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 pure form or diluted in a washing solution, with at least a portion of a surface or fabric and then optionally rinsed this surface or fabric. Preferably the surface or fabric is subjected to a washing step before the optional rinse step mentioned above. For the purposes of the present invention, washing includes but is not limited to scrubbing and mechanical agitation. As one skilled in the industry will understand, the cleaning compositions of the present invention are ideally suited for use in home care applications (hard surface cleaning compositions), personal care and / or laundry. Accordingly, the present invention includes a method for cleaning a surface and / or washing a fabric. The method comprises the steps of contacting a surface and / or cloth to be cleaned / washed with the modified alkoxylated polyol compound or a cleaning composition comprising the modified alkoxylated polyol compound. The surface may comprise most of the hard surfaces found in a typical home such as hardwood, tile, ceramic, plastic, leather, metal, glass, or may consist of cleaning surfaces in a personal care product such as hair and skin The surface may also include dishes, glasses, and other kitchen surfaces. Any fabric that the consumer usually launders under normal conditions can be used. The pH of the solution of the cleaning composition is chosen to be most complementary to a surface to be cleaned, covering a wide range of pH, from about 5 to about 11. For personal care such as cleaning the skin and the hair, the pH of this composition preferably has a pH of about 5 to about 8, for the laundry cleaner compositions a pH of about 8 to about 10. The compositions are preferably used in concentrations of about 200 ppm to about 10,000 ppm. in the solution. Water temperatures preferably range from about 5 ° C to about 100 ° C. For use in laundry cleaning compositions, the compositions are preferably used in concentrations of about 200 ppm to about 10,000 ppm in the solution (or wash solution). 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 includes a method for cleaning a surface or fabric. This 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 the 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, "non-woven substrate" may comprise any sheet or conventionally produced non-woven continuous material having suitable characteristics of basis weight, caliper (thickness), absorbency and strength. Examples of commercially available suitable nonwoven substrates include those marketed under the trademark SONTARA® by DuPont and POLYWEB® by James River Corp. As can be understood by one of ordinary skill in the industry, the cleaning compositions of the present invention are perfectly suited for use in hard surface applications. Therefore, 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 solution for hard surfaces or a 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 means of a user's hand or by using an implement to which the substrate is attached. non-woven. As one skilled in the industry will understand, the cleaning compositions of the present invention are perfectly suitable for use in liquid dishwashing composition. The method for using a liquid dishwashing composition of the present invention comprises the steps of contacting dirty dishes with an effective amount, usually from about 0.5 mL to about 20 mL (per 25 dishes being treated) of the liquid dishwashing composition. the present invention diluted in water. Suitable examples can be seen later in Table 5. In general, from about 0.01 mL to about 150 mL of a liquid dishwashing composition of the invention are combined with about 2000 mL to about 20,000 mL of water in a sink that has a volumetric capacity that varies from approximately 1000 mL to approximately 20,000 mL. The dirty dishes are submerged in the sink containing the diluted compositions, where they are cleaned by contacting the dirty surface of the dish with a cloth, sponge, or similar item. The cloth, sponge, or similar article may be immersed in the mixture of detergent composition and water before being contacted with the surface of the plate, and is usually contacted with the surface of the plate for a period of time ranging from about 1 to about 10. seconds. The contact of the cloth, sponge, or similar article to the surface of the plate is preferably accompanied by the concurrent scrubbing of the surface of the plate. Another method of use will comprise immersing dirty dishes in a water bath without any liquid dishwashing composition. A device for absorbing the liquid dishwashing composition, such as a sponge, is placed directly into a separate amount of undiluted liquid composition for washing dishes for a period of time which usually varies from about 1 to about 5 seconds. The absorbent device, and therefore the undiluted liquid composition for dishwashing, is then individually contacted to the surface of each of the soiled dishes to remove said soiled. The absorbent device is usually contacted with each surface of the dish for a period of time ranging from about 1 to about 10 seconds. The contact of the absorbent device to the surface of the plate is preferably accompanied by simultaneous scrubbing. As one skilled in the industry will understand, the cleaning compositions of the present invention are also suitable for use in personal care cleaning applications. Accordingly, the present invention includes a method for cleaning the skin or hair. The method comprises the steps of contacting a skin / hair to be cleaned with a cleaning solution or a nonwoven substrate impregnated with an embodiment of the cleaning compositions discussed herein. The method of using the nonwoven substrate when contacting the skin and hair can be by the hand of a user or by using an implement to which the nonwoven substrate is attached. Other compositions Other compositions containing the compound of the present invention can be used in personal care compositions such as contact lens solution, can be used as adhesives, in the vulcanization of rubbers, can be used in polyurethane manufacturing processes, in colorant compositions, as an ink composition, they can be used as a dispersant in agricultural applications such as a dispersant in an antifungal composition, among other compositions. Formulations
Table 1. Liquid laundry compositions
Polymer according to any of Examples 1-3 and Formulas I-IV of the present invention.
Table 2. Granulated low foam laundry compositions
1 - . 1 - Amidopropyldimethylamine C8-? Or 2- Amorphous sodium silicate (ratio 2.0; SiO2: Na20) SKS-6 3- Hydrated sodium aluminosilicate of the formula Na- ^ A ^ S ^) - ^ - 27H20 having a size of primary particle that varies from 0.1 to 10 micrometers. 4- Anhydrous sodium carbonate with a particle size between 200 μm and 900 μm 5- 4: 1 acrylic acid / maleic acid, average molecular weight of about 70,000 or 6: 4 acrylic acid / maleic acid, average molecular weight of about 10,000 ) "• Polymer according to any of Examples 1-3 or Formulas l-IV of the present invention 7- One or more of the enzymes such as:
Protease: proteolytic enzyme having 3.3% by weight of active enzyme commercialized by NOVO Industries A / S under the trademark SAVINASE®; Proteolytic enzyme having 4% by weight of active enzyme, as described in patent no. WO 95/10591, marketed by Genencor Int. Inc.
Alcalase: proteolytic enzyme having 5.3% by weight of active enzyme, marketed by NOVO Industries A / S Cellulase: cellulite enzyme having 0.23% by weight of active enzyme, marketed by NOVO Industries A / S under the trademark CAREZYME®. Amylase: amylolytic enzyme having 1.6% by weight of active enzyme, marketed by NOVO Industries A / S under the trademark TERMAMYL 120T®; amylolytic enzyme such as described in U.S. Pat. PCT no. 9,703,635. Lipase: lipolytic enzyme having 2.0% by weight of active enzyme, marketed by NOVO Industries A / S under the trademark LIPOLASE®; lipolytic enzyme having 2.0% by weight of active enzyme, marketed by NOVO Industries A / S under the trademark LIPOLASE ULTRA®.
Endolase: endogluconease enzyme having 1.5% by weight of active enzyme, marketed by NOVO Industries A / S.
Table 3. Granulated laundry compositions
1 • Sodium Tripolyphosphate 2- Zeolite A: Hydrated sodium aluminosilicate of the formula Nai2 (A1? 2Si? 2) i2-27H2O having a primary particle size ranging from 0.1 to 10 microns. 3- A modified alkoxylated polyol compound according to Examples 1-3 and Formula I-IV of the present application 4- Foam suppressant 5- Molecular weight = 4500 Table 4. Hard surface cleaning compositions
"- Polymer according to Examples 1-3 and Formulas l-IV of the present application 2- As emulsion Dow Corning AF Emulsion or polydimethylsiloxane
Table 5. Liquid dishwashing composition
1 • As described in U.S. Pat. no. 6,645,925 B1 2- A polymer according to Examples 1-3 and Formulas I-IV of the present invention.
The relevant part of all the documents cited in the Detailed Description section of the invention are incorporated by reference herein and it should not be inferred that the citation of said documents is the admission that they make up the prior industry with respect to the present invention. Even though the particular embodiments of the present invention have been illustrated and described, it will be clear to those with experience in the industry that various changes and modifications may be made without departing from the spirit and scope thereof. It has been intended, therefore, to cover in the appended claims all changes and modifications that are within the scope of the invention.
Claims (10)
1. A compound characterized by comprising a polyol source; the polyol source comprises at least three hydroxy portions, at least one of the hydroxy portions further comprises an alkoxy portion, the alkoxy portion is selected from the group comprising ethoxy, propoxy, butoxy and mixtures thereof; and wherein at least one of the hydroxy portions further comprises an anionic coronation unit.
2. A compound characterized by comprising a polyol source; the polyol source comprises at least three hydroxy portions, at least one of the hydroxy portions further comprises an alkoxy portion, the alkoxy portion is selected from the group comprising ethoxy, propoxy, butoxy and mixtures thereof; and wherein at least one of the hydroxy portions further comprises an anionic coronation unit, and at least one of the hydroxy portions is replaced by an amine coronation unit.
3. A compound characterized by comprising a polyol source; the polyol source comprises at least three hydroxy portions, at least one of the hydroxy portions further comprises an alkoxy portion, the alkoxy portion is selected from the group comprising ethoxy, propoxy, butoxy and mixtures thereof; and wherein at least one of the hydroxy portions further comprises an anionic coronation unit, and at least one of the hydroxy portions is replaced by a quaternary amine coronation unit.
4. A compound characterized by comprising a polyol source; the polyol source comprises at least three hydroxy portions, at least one of the hydroxy portions further comprises an alkoxy portion, the alkoxy portion is selected from the group comprising ethoxy, propoxy, butoxy and mixtures thereof; and wherein at least one of the hydroxy portions further comprises an anionic coronation unit, at least one of the hydroxy portions is replaced by an amine coronation unit and at least one of the hydroxy portions is replaced by a unit of coronation of quaternary amine. The compound according to claim 1, further characterized in that the hydroxy portions comprise the alkoxy portion comprising an average degree of alkoxylation per hydroxy portion of 1 to 100. The compound according to any of claims 1 to
5. , further characterized in that at least one of the anionic coronation units is replaced by an amine coronation unit. The compound according to any of claims 2 or 4, further characterized in that the amine coronation unit is selected from the group comprising ammonia, methylamine, dimethylamine, ethylenediamine, dimethylaminopropylamine, bis dimethylaminopropylamine (bis DMAPA), hexamethylenediamine, ethylamine , diethylamine, dodecylamine, benzylamine, polyethylene imine, isoquinoline, tallow triethylenediamine, mono-substituted monoamine, mono-substituted diamine, mono-substituted polyamine, di-substituted monoamylamine, di-substituted diamine, di-substituted polyamine, tri-substituted triamine, tri-substituted polyamine, multi-substituted polyamine comprising more than three substitutions, provided that at least one nitrogen contains a hydrogen, and mixtures thereof. The compound according to any of claims 1, 2, 3, or 4, further characterized in that the polyol compound is derived from sugar or monomers of reduced sugar which is selected from the group comprising glucose, maltose, maltotriose, maltopentose , maltohexose sorbitol, maltitol, sucrose, xylitol, glycerol, glycerol derivatives, polyglycerol, pentaerithitol, polyvinyl alcohol, xylan, reduced maltotriose, reduced maltodextrins, and mixtures thereof. 9. A cleaning composition comprising a compound, characterized in that it comprises the compound according to any of claims 1, 2, 3, or 4. 10. The cleaning composition according to claim 9, further characterized in that the cleaning composition further includes a chosen anionic, nonionic cationic, zwitterionic, amphoteric surfactant, and mixtures thereof.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US53138503P | 2003-12-19 | 2003-12-19 | |
PCT/US2004/043074 WO2005063847A1 (en) | 2003-12-19 | 2004-12-17 | Modified alkoxylated polyol compounds |
Publications (1)
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MXPA06007020A true MXPA06007020A (en) | 2006-08-31 |
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MXPA06007020A MXPA06007020A (en) | 2003-12-19 | 2004-12-17 | Modified alkoxylated polyol compounds. |
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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) |
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CA2589395A1 (en) | 2004-12-17 | 2006-06-22 | The Procter & Gamble Company | Hydrophilically modified polyols for improved hydrophobic soil cleaning |
CA2590434A1 (en) | 2004-12-17 | 2006-06-22 | The Procter & Gamble Company | Hydrophobically modified polyols for improved hydrophobic soil cleaning |
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 |
WO2007144819A1 (en) | 2006-06-12 | 2007-12-21 | The Procter & Gamble Company | A 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 |
FR3111901B1 (en) * | 2020-06-30 | 2023-02-17 | Arkema France | IMPROVED ALCOXYLATION PROCESS |
WO2022082285A1 (en) * | 2020-10-19 | 2022-04-28 | 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)
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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 | Process for producing monoglyceride disulfate and monoglyceride sulfate containing the disulfate |
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 | Method for producing N-alkylamide alkanol sulfate 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 | Manufacturing method of 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 |
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2004
- 2004-12-17 WO PCT/US2004/043074 patent/WO2005063847A1/en not_active Application Discontinuation
- 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 JP JP2006544144A patent/JP2007520459A/en active Pending
- 2004-12-17 MX MXPA06007020A patent/MXPA06007020A/en active IP Right Grant
- 2004-12-17 CN CN2004800378221A patent/CN1894305B/en not_active Expired - Fee Related
- 2004-12-17 CA CA002549571A patent/CA2549571A1/en not_active Abandoned
- 2004-12-17 EP EP04815188A patent/EP1694741A1/en not_active Withdrawn
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JP2007520459A (en) | 2007-07-26 |
WO2005063847A1 (en) | 2005-07-14 |
CA2549571A1 (en) | 2005-07-14 |
EP1694741A1 (en) | 2006-08-30 |
BRPI0417536A (en) | 2007-03-27 |
CN1894305A (en) | 2007-01-10 |
AR047292A1 (en) | 2006-01-11 |
CN1894305B (en) | 2010-10-13 |
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