EP0948393A1 - Waschmittelzusammensetzungen mit geringer konzentration an geminitensiden - Google Patents
Waschmittelzusammensetzungen mit geringer konzentration an geminitensidenInfo
- Publication number
- EP0948393A1 EP0948393A1 EP97942138A EP97942138A EP0948393A1 EP 0948393 A1 EP0948393 A1 EP 0948393A1 EP 97942138 A EP97942138 A EP 97942138A EP 97942138 A EP97942138 A EP 97942138A EP 0948393 A1 EP0948393 A1 EP 0948393A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- surfactant
- alkyl
- composition
- weight
- independently
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 210
- 239000000203 mixture Substances 0.000 title claims abstract description 123
- 239000003599 detergent Substances 0.000 title description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- -1 organic base salt Chemical group 0.000 claims description 79
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical group 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 description 45
- 150000001875 compounds Chemical class 0.000 description 33
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 32
- 235000014113 dietary fatty acids Nutrition 0.000 description 29
- 229930195729 fatty acid Natural products 0.000 description 29
- 239000000194 fatty acid Substances 0.000 description 29
- 239000002736 nonionic surfactant Substances 0.000 description 28
- 239000007859 condensation product Substances 0.000 description 24
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 22
- 150000004665 fatty acids Chemical class 0.000 description 22
- 235000002639 sodium chloride Nutrition 0.000 description 21
- 239000011734 sodium Substances 0.000 description 20
- 229910052708 sodium Inorganic materials 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000003945 anionic surfactant Substances 0.000 description 14
- 239000000839 emulsion Substances 0.000 description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 14
- 239000002280 amphoteric surfactant Substances 0.000 description 13
- 125000000129 anionic group Chemical group 0.000 description 12
- 150000001450 anions Chemical class 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000004744 fabric Substances 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 125000002091 cationic group Chemical group 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000003760 tallow Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000002209 hydrophobic effect Effects 0.000 description 8
- 125000001165 hydrophobic group Chemical group 0.000 description 8
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000000344 soap Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000003093 cationic surfactant Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000004996 alkyl benzenes Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 5
- 235000019438 castor oil Nutrition 0.000 description 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002453 shampoo Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000003240 coconut oil Substances 0.000 description 4
- 235000019864 coconut oil Nutrition 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 238000004945 emulsification Methods 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 150000008054 sulfonate salts Chemical class 0.000 description 4
- NEOAZCPSMNVSPK-UHFFFAOYSA-N 2-[(2-hydroxy-6-octylphenyl)methyl]-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1CC1=C(O)C=CC=C1CCCCCCCC NEOAZCPSMNVSPK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 150000008051 alkyl sulfates Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229940096386 coconut alcohol Drugs 0.000 description 3
- 230000003750 conditioning effect Effects 0.000 description 3
- QKQCPXJIOJLHAL-UHFFFAOYSA-L disodium;2-[2-(carboxylatomethoxy)ethyl-[2-(dodecanoylamino)ethyl]amino]acetate Chemical compound [Na+].[Na+].CCCCCCCCCCCC(=O)NCCN(CC([O-])=O)CCOCC([O-])=O QKQCPXJIOJLHAL-UHFFFAOYSA-L 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical group COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 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 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000004581 coalescence Methods 0.000 description 2
- 229940071195 cocoamphodipropionate Drugs 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 239000002979 fabric softener Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000008233 hard water Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229940039717 lanolin Drugs 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 229940071188 lauroamphodiacetate Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 231100000344 non-irritating Toxicity 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- OXGBCSQEKCRCHN-UHFFFAOYSA-N octadecan-2-ol Chemical compound CCCCCCCCCCCCCCCCC(C)O OXGBCSQEKCRCHN-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- FNRRHKQTVNDRSJ-UHFFFAOYSA-N 2,3-bis(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC(O)=C1CCCCCC(C)C FNRRHKQTVNDRSJ-UHFFFAOYSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- SMDSVTVQKNWUIN-UHFFFAOYSA-N 2-non-8-enyl-3-octylphenol Chemical compound C=CCCCCCCCC1=C(C=CC=C1CCCCCCCC)O SMDSVTVQKNWUIN-UHFFFAOYSA-N 0.000 description 1
- PTFIPECGHSYQNR-UHFFFAOYSA-N 3-Pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 1
- MSTWJNRTDPVXOC-UHFFFAOYSA-N 4-pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=C(O)C=C1 MSTWJNRTDPVXOC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000019737 Animal fat Nutrition 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920004897 Triton X-45 Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005192 alkyl ethylene group Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- 229960001950 benzethonium chloride Drugs 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940071105 caproamphodipropionate Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940096362 cocoamphoacetate Drugs 0.000 description 1
- 229940047648 cocoamphodiacetate Drugs 0.000 description 1
- 229920013750 conditioning polymer Polymers 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- QUOSBWWYRCGTMI-UHFFFAOYSA-L disodium;2-[2-(carboxylatomethoxy)ethyl-[2-(decanoylamino)ethyl]amino]acetate Chemical compound [Na+].[Na+].CCCCCCCCCC(=O)NCCN(CC([O-])=O)CCOCC([O-])=O QUOSBWWYRCGTMI-UHFFFAOYSA-L 0.000 description 1
- WYHYDRAHICKYDJ-UHFFFAOYSA-L disodium;3-[2-(2-carboxylatoethoxy)ethyl-[2-(decanoylamino)ethyl]amino]propanoate Chemical compound [Na+].[Na+].CCCCCCCCCC(=O)NCCN(CCC([O-])=O)CCOCCC([O-])=O WYHYDRAHICKYDJ-UHFFFAOYSA-L 0.000 description 1
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 1
- WWYHAQDAMPXWSI-UHFFFAOYSA-N dodecan-1-ol;methane Chemical compound C.CCCCCCCCCCCCO WWYHAQDAMPXWSI-UHFFFAOYSA-N 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- ACDUHTSVVVHMGU-UHFFFAOYSA-N hexadecan-3-ol Chemical compound CCCCCCCCCCCCCC(O)CC ACDUHTSVVVHMGU-UHFFFAOYSA-N 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- BTTMZEBIMDNSPK-UHFFFAOYSA-N icosan-4-ol Chemical compound CCCCCCCCCCCCCCCCC(O)CCC BTTMZEBIMDNSPK-UHFFFAOYSA-N 0.000 description 1
- WLIISNIPNDLIFS-UHFFFAOYSA-N icosan-5-ol Chemical compound CCCCCCCCCCCCCCCC(O)CCCC WLIISNIPNDLIFS-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- UOZFSLAMWIZUEN-UHFFFAOYSA-M sodium;2-[2-(decanoylamino)ethyl-(2-hydroxyethyl)amino]acetate Chemical compound [Na+].CCCCCCCCCC(=O)NCCN(CCO)CC([O-])=O UOZFSLAMWIZUEN-UHFFFAOYSA-M 0.000 description 1
- ZKBGPOVFSMIXBF-UHFFFAOYSA-M sodium;2-[2-hydroxyethyl-[2-(octadecanoylamino)ethyl]amino]acetate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC(=O)NCCN(CCO)CC([O-])=O ZKBGPOVFSMIXBF-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
- 229940066732 stearoamphoacetate Drugs 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical class CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/18—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/14—Derivatives of phosphoric acid
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/40—Monoamines or polyamines; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
Definitions
- This invention relates to improved surfactant systems useful as emulsifiers and in detergents at very low concentration.
- Emulsification is an extremely important technology and it is a process which is used in detergencN .
- Emulsifiers function as essential ingredients in personal care and household products, industrial and institutional cleaners including shampoo, car washes, carpet shampoo, hand dishwashing liquids, latex foaming and oil recovery compositions: and the like
- an emulsifier is required to adsorb at an oil-water interface to prevent emulsion ⁇ roplet coalescence
- the maio ⁇ n of emulsifiers are synthetic surfactants or natural products with amphiphiiic character
- usage levels of surfactants for effective emulsification are usually above 0.1% active based on the total weight of the detergent solution which is used in the final use composition.
- gemini surfactant For a given emulsifier system, it would be advantageous to use a lower amount of surfactant to reduce the cost and amount of surfactant waste discharged into the environment: and to improve the performance of final products (e.g.. the film forming and water resistance will be improved in latex paints and skin irritation will be reduced for cosmetic pro ⁇ ucts with less surfactants )
- conventional surfactants generally have one hydrophilic group and one hydrophobic group
- Recently a class of compounds having at least two hydrophobic groups and at least two hydrophilic groups have been introduced. These have become known as "gemini surfactants" in the literature (Chemtech. March 1993, pp 30 - 33), and J. American Chemical Soc. 1 5. 10083-10090. (1993) and the references cited therein).
- Other gemini surfactant compounds that is. compounds having at least two hydrophilic groups and at least two hydrophobic groups are also disclosed in literature but often are not referred to expressly as gemini surfactants.
- gemini surfactants as emulsifiers. From these studies, it has been found that gemini surfactants are unexpectedly effective emulsifiers when used at very low concentrations in comparison to conventional surfactants. This finding is reflected in superior detergencv at very low concentrations. Other performance properties related to emulsification as mentioned above can be also improved using low concentrations of gemini surfactants.
- gemini surfactants of the type described and claimed herein can be extremely effective emulsifiers for oil-in-water emulsions at lower concentrations than that needed
- Figures 1 and 2 are bar graphs representing the comparison of detergencv of polyoxyethylene (13) methylene bis (octylphenol) (MBOP) versus a control of polyoxyethylene (7.5) octylphenol (OP) on different fabrics at 0.005% & 0.01 % by weight respectively.
- Figures 3 and 4 are bar graphs representing the comparison of detergencv of polyoxyethylene(13) methylene bis (octylphenol) (MBOP) in a 1 : 1 blend with sodium
- dodecylbenzene sulfonate versus a control of polyoxyethylene (7.5) octylphenol (OP)in a 1 :1 blend with the same sulfonate on various fabrics at 0.001% & 0.005% by weight
- gemini surfactants is intended to mean surfactants having at least 2 hydrophobic groups and at least 2 hydrophilic groups per molecule.
- gemini surfactants are reported in the literature, see for example. Okahara et al. J. Japan Oil Chem. Soc. 746 (Yukagaku) (1989); Zhu et al..
- gemini surfactants are disclosed by U.S. Patent Nos. 2,374.354. Kaplan; 2.524.218, Bersworth; 2.530.147 Bersworth (two hydrophobic tails and three hydrophilic heads); 3.244.724. Gu ⁇ mann; 5,160,450. Okahara. et al., all of which are incorporated herein by reference.
- the gemini surfactants may be anionic. nonionic. cationic or amphoteric.
- the hydrophilic and hydrophobic groups of each surfactant moiety (A,A ! ) may be any of those known to be used in conventional surfactants having one hydrophilic group and one hydrophobic group.
- a typical nonionic gemini surfactant e.g.. a bis-polyoxyethylene alkyl ether
- Each moiety would contain a hydrophilic group, e.g., polyoxyethylene. and a hydrophobic group, e.g., an alkyl chain.
- Anionic and nonionic gemini surfactants which are. useful in the present invention include those of the formula: R,
- R is independently C, to C 2 alkyl.
- R 4 C(0) -. or R -B-R 5 -
- R4 is C, to C alkyl.
- R is C, to C 12 alkyl.
- B is an amide group.
- a carboxyl group [ -C(0)-0- ].
- a carbonyl group, and a polyether group [ -0(EO) a PO) h - ] wherein EO represents ethyleneoxy radicals.
- PO represents propyleneoxv radicals
- a and b are numbers of from 0 to 100, a is preferably from about 0 to about 30 and b is preferably from about 0 to 10. wherein a plus b is at least one, and the EO and PO radicals can be randomly mixed or in discrete blocks, and R ⁇ is hydrogen or C ⁇ to C 6
- R ⁇ is independently hydrogen or C, to C 22 alkyl
- R 2 is independently a C r C j0 alkyl. -0-. an amide group [ -C(0)N(R 6 )- ]. a polyether group [ -0(EO) a (PO) b - ]. -R 7 -D-R 7 - or
- R 7 is independently a C, -C 6 alkyl and D is -0-.
- -S-. an amide group [ -C(0)N(R 6 )- ], or an amino group [ -N ⁇ Rg)- ], wherein ⁇ , , a and b are as defined above, and t is independently 0 or 1.
- Z is independently hydrogen. -S0 3 Y, -P(0)(OY) 2 . -COOY, -CH 2 COOY, -CH 2 -CH(OH)CH 2 S0 3 Y and when R 2 is not a polyether.
- Z is also -OS0 3 Y. and - OP(0)(OY) 2 : wherein Y is hydrogen, alkali metal such as sodium and potassium; alkaline earth metal such as magnesium and calcium: ammonium: or organic base salt such as monoethanolamine. diethanolamine. triethanolamine. triethylamine, trimethylamine. N-hydroxyethyl morpholine. and the like.
- A is independently a straight chain or branched C, to C 6 alkyl.
- R 3 is a bond, an aryl group such as a
- phenyl or diphenyl group a C, to C I0 alkyl group, preferably a C, to C 4 alkyl group, most preferably methylene. -0-. -S-, -S-S-. -N(R 6 )-. -R 5 -0-. -R 5 [0(EO) a (PO) b -].
- alkali * includes substituted alkali, especially the hydroxy substituted derivatives thereof and straight as well as branched chains.
- Z is hydrogen
- the gemini surfactants are nonionic.
- gemini surfactants specifically useful in the present invention include gemini anionic or nonionic surfactants of the formulae:
- R c represents aryl, preferably phenyl.
- R 3 . R 4 . Y. Z. a and b are as defined above. More specifically, these compounds comprise:
- R 4 , R 5 , Z. a. and b are as defined hereinbefore.
- the primary hydroxyl group of these surfactants can be readih phosphated. sulfated or carboxylated by standard techniques.
- the compounds included in Formula II can be prepared by a variety of synthetic routes.
- the compounds of Formula IV can be prepared by condensing a monoalkyl phenol with paraformaldehyde in the presence of an acid catalyst such as acetic acid.
- the compounds of Formula V can be synthesized by a Lewis acid catalyzed reaction of an alkylphenol with a dicarboxylic acid, e.g., terephthalic acid.
- a class of gemini surfactants that can be used in providing the improved emulsions which are operable at lower concentrations as disclosed in the present invention include a group of amphote ⁇ c, and cationic quaternan surfactants comprising compounds of the formula VII.
- R. wherein R. t, and Z are as defined hereinbefore.
- R is as defined before and includes the [ -(EO) a (PO) b O- ]H moiety.
- R 2 is as defined before, however, D includes the
- R 3 is selected from the group consisting of a bond.
- the compounds of Formula VII comprise:
- R. R 2 . R . Z. and n are as defined hereinbefore: and m independently equals a number between about 2 and about 10.
- Representative compounds of Formula VII include.
- R 9 is independently a C
- the compounds used in the present invention comprise those of
- R 3 is a C, - C 4 alkyl. most preferably ethyl.
- Ro is a lower alkyl of from 1 to about 4 carbon atoms, most preferably methyl: and X is halogen or methylsulfate.
- the compounds of Formula XIII can be prepared by a variety of snythetic processes.
- gemini surfactants useful in this invention are those of the formula: R 13 -(CH,) p -N-R 14
- R, 3 is a sugar moiety, e.g.. a monosaccharide. desaccharide, or polvsaccharide such as glucose: or a polyhydroxy compound such as glycerol; p is independently 0 to 4: R 3 is as defined above in formula VII; and R M is a C r C, 2 alkyl or -C(0)R 4 wherein R 4 is as described above.
- many of the moieties can be derived from natural sources which will generally contain mixtures of different saturated and unsaturated carbon chain lengths.
- the natural sources can be illustrated by coconut oil or similar natural oil sources such as palm kernel oil. palm oil. osya oil. rapeseed oil.
- the fatty acids from natural sources in the form of the fatty acid or the triglyceride oil can be a mixture of alkyl radicals containing from about 5 to about 22 carbon atoms.
- Illustrative of the natural fatty acids are caprylic (C 8 ). capric (C 10 ). lauric (C,,). myristic (C, 4 ). palmitic (C, 6 ). stearic (C 18 ). oleic (C 18 . monounsaturated). linoleic (C, g , diunsaturated). linolenic (C, 8 . triunsaturated). ricinoleic (C 18 . monounsaturated)
- These fatty acids can be used per se. as concentrated cuts or as fractionations of natural source acids.
- the fatty acids with even numbered carbon chain lengths are given as illustrative though the odd numbered fatty acids can also be used.
- single fatty acids with even numbered carbon chain lengths are given as illustrative though the odd numbered fatty acids can also be used.
- carboxylic acids e.g.. lauric acid, or other cuts, as suited for the particular application, may be used.
- the surfactants used in the present invention can be oxyalkylated by reacting the product with an alkylene oxide according to known methods, preferably in the presence of an alkaline catalyst.
- the free hydroxyl groups of the alkoxylated derivative can then be sulfated.
- phosphated or acylated using normal methods such as sulfation with sulfamic acid or sulfur trioxide-pyridine complex, or acylation with an acylating agent such as a carboxylic acid, ester, and the naturally occurring triglyceride esters thereof.
- the surfactant compositions of the invention are extremely effective in aqueous solution at low concentrations as defined herein.
- the surfactants of the invention can be used in any amount needed for a particular application which can be easily determined by a skilled artisan without undue experimentation.
- W ile the gemini surfactants of the invention can be used alone, it has been unexpectedly found that blends of the compounds of the invention with certain other conventional well known anionic, nonionic. cationic and amphoteric surfactants provide synergistic effects in relation to critical micelle concentration (cmc) and surface tension reducing ability, and hence improved detergencv.
- cmc critical micelle concentration
- Nonionic surfactants including those having an HLB of from 5 to 17. are well known in the detergency art. Examples of such surfactants are listed in U.S. Patent No.
- Nonlimiting examples of suitable nonionic surfactants which may be used in the present invention are as follows:
- the polyethylene oxide condensates of alkyl phenols. These compounds include the condensation products of alkyl phenols having an alkyl group containing from about 6 to 12 carbon atoms in either a straight chain or branched chain configuration with ethylene oxide, said ethylene oxide being present in an amount equal to 5 to 25 moles of ethylene oxide per mole of alkyl phenol.
- the alkyl substituent in such compounds can be derived, for example. from polymerized propylene. diisobutylene. and the like. Examples of
- nonionic surfactants of this type include Igepal CO-630. marketed by Rhone-Poulenc Inc. and Triton X-45, X-1 14, X- 100, and X-102, all marketed by Union Carbide.
- the condensation products of aliphatic alcohols with from about 1 to about 25 moles of ethylene oxide can either be straight or branched, primary or secondary, and generally contains from about 8 to about 22 carbon atoms.
- Examples of such ethoxylated alcohols include the condensation product of myristyl alcohol condensed with about 10 moles of ethylene oxide per mole of alcohol; and the condensation product of about 9
- Neodol 15-S- 9. marketed by Union Carbide Corporation.
- Neodol 45-7. and Neodol 45-4. marketed by Shell Chemical Company.
- the hydrophobic portion of these compounds typically has a molecular weight of from about 1500 to 1800 and exhibits water insolubility.
- the addition of polyoxyethylene moieties to this hydrophobic portion tends to increase the water solubility of the molecule as a whole, and the liquid character of the product is retained up to the point where the polyoxyethylene content is about 50%) of the total weight of the condensation product, which corresponds to condensation with up to about 40 moles of ethylene oxide.
- Examples of compounds of this type include certain of the commercially available Pluronic surfactants, marketed by Wyandotte Chemical Corporation.
- the condensation products of ethylene oxide with the product resulting from the reaction of propylene oxide and e hylenediamine The hydrophobic moiety of these products consists of the reaction product of ethylenediamine and excess propylene oxide, said moiety having a molecular weight of from about 2500 to about 3000.
- This hydrophobic moiety is condensed with ethylene oxide to the extent that the condensation product contains from about 40% to about 80%) by weight of polyoxyethylene and has a molecular weight of from about 5.000 to about 1 1 ,000.
- Examples of this type of nonionic surfactant include certain of the commercially available Tetroni ⁇ compounds, marketed by Wyandotte Chemical Corporation.
- Semi-polar nonionic detergent surfactants include water-soluble amine oxides containing one alkyl moiety of from about 10 to 18 carbon atoms and 2
- moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from 1 to about 3 carbon atoms water-soluble phosphine oxides containing one alkyl moiety of about 10 to 18 carbon atoms and 2 moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from about 1 to 3 carbons atoms: and water-soluble sulfoxides containing one alkyl moiety of from about 10 to 18 carbon atoms and a moiety selected from the group consisting of alkyl and hydroxyalkyl moieties of from about 1 to 3 carbon atoms.
- Preferred semi-polar nonionic detergent surfactants are the amine oxide
- detergent surfactants having the formula:
- R 1 is an alkyl, hydroxy alkyl, or alkyl phenyl group or mixtures thereof containing from about 8 to about 22 carbon atoms.
- R is an alkylene or hydroxy alkylene group containing from 2 to 3 carbon atoms or mixtures thereof, x is from 0 to about 3 and each R is an alkyl or hydroxy alkyl group containing from 1 to about 3 carbon atoms or a_polyethylene oxide group containing from one to about 3 ethylene oxide groups and said R groups can be attached to each other, e.g.. through an oxygen or nitrogen atom to form a ring structure.
- Preferred amine oxide detergent surfactants are C ] 0 -Cj 8 alkyl dimethyl amine oxide.
- Nonionic detergent surfactants ( l )-(4) are conventional ethoxylated nonionic detergent surfactants and mixtures thereof can be used.
- Preferred alcohol ethoxylate nonionic surfactants for use in the compositions of the liquid, powder, and gel applications are biodegradable and have the formula R(OC,H 4 ) n OH wherein R is a primary or secondary alkyl chain of from about 8 to about 22. preferably from about 10 to about 20 carbon atoms and n is an average of from about 2 to about 12. particularly from about 2 to about 9.
- the nonionics have an HLB (hydrophilic-lipophilic balance) of from about 5 to about 17. preferably from about 6 about 15 HLB is defined in detail in Nonionic Surfactants, by M J Schick. Marcel Dekker. Inc., 1966, pages 606-613. incorporated herein by reference In preferred
- n is from 3 to 7
- Primary linear alcohol ethoxvlates e.g , alcohol ethoxylates produced from organic alcohols which contain about 20% > 2-methyl branched isomers, commercially available from Shell Chemical Company under the trademark Neodol
- Neodol are preferred from a performance standpoint
- nonionic surfactants are preferably solids at room temperature with a melting point above about 25° C , preferabh above about 30° C Bar compositions of the present invention made with lower melting nonionic surfactants are generally too soft, not meeting the bar firmness requirements of the present invention.
- nonionic surfactants usable herein, but not limited to bar applications, include fatty acid glycerine and polyglycerine esters, sorbitan sucrose fatty acid esters, polyoxyethylene alkyl and alkyl allyl ethers, polyoxyethylene lanolin alcohol, glycerine and polyoxyethylene glycerine fatty acid esters, polyoxyethylene propylene glycol and sorbitol fatty acid esters, polyoxyethylene lanolin, castor oil or hardened castor oil derivatives, polyoxyethylene fatty acid amides, polyoxyethylene alkyl amines, alkylpyrrolidone, glucamides, alkylpolyglucosides. and mono- and dialkanol amides.
- Typical fatty acid glycerine and polyglycerine esters as well as typical sorbitan sucrose fatty acid esters, fatty acid amides, and polyethylene oxide/polypropylene oxide block copolvmers are disclosed by U.S. Patent No. 5.510.042. Hartman et al. incorporated herein by reference.
- the castor oil derivatives are typically ethoxylated castor oil. It is noted that other ethoxylated natural fats, oils or waxes are also suitable.
- Polyoxyethylene fatty acid amides are made by ethoxylation of fatty acid amides with one or two moles of ethylene oxide or by condensing mono-or diethanol amines with fatty acid.
- Polyoxyethylene alkyl amines include those of formula: RNH-(CH,CH,0) n -H. wherein R is C 6 to C,, alkyl and n is from 1 to about 100.
- Monoalkanol amides include those of formula: RCONHR'OH. wherein R is C 6 -C 2 alkyl and R is C, to C 6 alkylene.
- Dialkanol amides are typically mixtures of: diethanolamide: RCON(CH,CH,OH) 2 ; amide ester: RCON(CH,CH,OH)-CH,CH,OOCR; amine ester: RCOOCH,CH,NHCH,CH,OH; and amine soap: RCOOH,N(CH,CH,OH) 2 , wherein R in the above formulas is an alkyl of from 6 to 22 carbon atoms.
- Examples of preferred but not limiting surfactants for detergent bar products are the following:
- deca-, undeca-. dodeca-, tetradeca-. and pentadeca-ethoxylates of n- hexadecanol. and n-hexadecanol. and n-octadecanol having an HLB within the range recited herein are useful nonionics in the context of this -invention.
- Exemplary ethoxylated primary alcohols useful herein as the conventional nonionic surfactants of the compositions are n-C 18 EO(10): n-C 14 EO(13): and n-C 10 EO( l 1 ).
- the ethoxvlates of mixed natural or synthetic alcohols in the "tallow ** chain length range are also useful herein.
- Specific examples of such materials include tallow-alcohol-EO(l 1 ).
- Exemplary ethoxylated secondary alcohols useful herein are 2- C l EO(l 1); 2-C 20 EO(l 1 ): and 2-C 16 EOf 14).
- the hexa- through octadeca- ethoxylates of alkylated phenols, particularly monohyd ⁇ c alkylphenols. having an HLB within the range recited herein are useful as conventional nonionic surfactants in the instant compositions
- ethoxylated alkylphenols useful in the mixtures herein are p-t ⁇ dec> Iphenol EO(l l ) and p- pentadecylphenol EO(18) Especially preferred is Nonyl Nonoxynol-49 known as Igepal* DM-880 from Rhone-Poulenc Inc
- a phenylene group in the nonionic formula is the equivalent of an alkylene group containing from 2 to 4 carbon atoms
- nonionics containing a phenylene group are considered to contain an equivalent number of carbon atoms calculated as the sum of the carbon atoms in the alkyl group plus about 3 3 carbon atoms for each phenvlene group Olefinic Alkoxylates
- alkenyl alcohols both p ⁇ man and seconda ⁇ and alkenvl phenols corresponding to those disclosed immediately here ⁇ nabo ⁇ e can be ethoxylated to an HLB within the range recited herein and used as the conventional nonionic surfactants of the instant compositions
- Branched chain primary and seconda alcohols which are available can be ethoxylated and employed as conventional nonionic surfactants in compositions herein
- the above ethoxylated nonionic surfactants are useful in the present compositions alone or in combination, and the term "nonionic surfactant" encompasses mixed nonionic surface active agents.
- nonionic surfactants of this invention include alkylpolysaccharides, preferably alkylpolyglucosides of the formula:
- R is a hydrophobic group selected from the group consisting of a C
- compositions of the present invention can also comprise mixtures of the above nonionic surfactants.
- Anionic surfactants include any of the known hydrophobes attached to a carboxylate. sulfonate.
- Salts may be the sodium, potassium, ammonium and amine salts of such surfactants
- Useful anionic surfactants can be organic sulfunc reaction products having in their molecular structure an alkyl group containing from about 8 to about 22 carbon atoms and a sulfomc acid or sulfunc acid ester group, or mixtures thereof (Included in the
- alkyl is the alkyl portion of acyl groups )
- alkyl sulfates especially those obtained by sulfating the higher alcohols (C 8 -C l g carbon atoms) produced from the glyce ⁇ des of tallow or coconut oil.
- alkyl benzene sulfonates are the alkyl sulfates. especially those obtained by sulfating the higher alcohols (C 8 -C l g carbon atoms) produced from the glyce ⁇ des of tallow or coconut oil.
- esters of alpha-sulfonated fatty acids preferably containing from about 6 to 20 carbon atoms in the ester group
- 2- acvloxvalkane-1 -sulfomc acids preferably containing from about 2 to 9 carbon atoms in the ac ⁇ l group and from about 9 to about 23 carbon atoms in the alkane moiety
- alkyl ether sulfates preferably containing from about 10 to 20 carbon atoms in the alkyl group and from about 1 to 30 moles of ethylene oxide, olefin sulfonates preferabh containing from about 12 to 24 carbon atoms, and beta-alkvloxv alkane sulfonates preferably containing from about 1 to 3 carbon atoms in the alkyl group and from about 8 to 20 carbon atoms in the alkane moiety
- Anionic surfactants based on the higher fatty acids, l e ' soaps "" are useful anionic surfactants herein Higher fatn acids containing from about 8 to about 24 carbon atoms and preferably from about 10 to about 20 carbon atoms and the coconut and tallow soaps can also be used herein as corrosion inhibitors
- Preferred water-soluble anionic organic surfactants herein include linear alkyl benzene sulfonates containing from about 10 to about 18 carbon atoms in the alkyl group; branched alkyl benzene sulfonates containing from about 10 to about 18 carbon
- alkyl group atoms in the alkyl group; the tallow range alkyl sulfates; the coconut range alkyl glyceryl sulfonates; alkyl ether (ethoxylated) sulfates wherein the alkyl moiety contains from about 12 to 18 carbon atoms and wherein the average degree of ethoxylation varies between " 1 and 12. especially 3 to 9; the sulfated condensation products of tallow alcohol with from about 3 to 12, especially 6 to 9. moles of ethylene oxide: and olefin sulfonates containing from about 14 to 16 carbon atoms.
- Specific preferred anionics for use herein include: the linear C !
- LAS 0 -C M alkvl benzene sulfonates
- ABS branched C ]0 -C ]4 alkyl benzene sulfonates
- tallow alkyl " sulfates the coconut alkyl glyceryl ether sulfonates
- commercial grades of the surfactants can contain non-interfering components which are processing by-products.
- commercial alkaryl sulfonates preferably C 10 -C 14
- anionic surfactants used herein include fatty acid soaps,
- ether carboxylic acids and salts thereof alkane sulfonate salts, ⁇ -olefin sulfonate salts. sulfonate salts of higher fatty acid esters, higher alcohol sulfate ester or ether ester
- alkyl preferably higher alcohol phosphate ester and ether ester salts, and condensates of higher fatty acids and amino acids.
- Fatty acid soaps include those having the formula: R-C(0)OM, wherein R is C 6 to C 22 alkyl and M is preferably sodium.
- Salts of ether carboxylic acids and salts thereof include those having the formula: R-(OR') n -OCH,C(0)OM. wherein R is C 6 to C,, alkyl. R 1 is C, to C, 0 , preferably C, alkyl. and M is preferably sodium.
- Alkane sulfonate salts and ⁇ -olefin sulfonate salts have the formula: R- S0 3 M. wherein R is C 6 to C 2 alkyl or ⁇ -olefin. respectively, and M is preferably
- Sulfonate salts of higher fatty acid esters include those having the formula:
- R is C I2 to C 22 alkyl
- R is C ⁇ to C 18 alkyl
- M is preferably sodium.
- Higher alcohol sulfate ester salts include those having the formula:
- R is C,,-C,, alkyl.
- R is C,-C 18 hydroxyalkyl.
- M is preferably sodium.
- Higher alcohol sulfate ether ester salts include those having the formula: RC(0)(OCH,CH,) X -R' -OS0 3 M. wherein R is C 12 -C, 2 alkyl. R is C r C 18 hydroxyalkyl. M is preferably sodium and x is
- Higher alcohol phosphate ester and ether ester salts include compounds of the
- R-(OR l ) n -0) 3 -PO wherein R is alkyl or hydroxyalkyl of 12 to 22 carbon atoms, R 1 is C 2 H 4 , n is an integer from 5 to 25. and M is preferably sodium.
- anionic surfactants herein are sodium coconut oil fatty acid monoglyceride sulfonates and sulfates; sodium or potassium salts of alkyl phenol ethylene oxide ether sulfates containing from about 1 to about 10 units of ethylene oxide per molecule and wherein the alkyl groups contain from about 8 to about 12 carbon atoms; and sodium or potassium salts of alkyl ethylene oxide ether sulfates containing about 1 to about 10 units of ethylene oxide per molecule and wherein the alkyl group contains from about 10 to about 20 carbon atoms.
- C. Cationic Surfactants Preferred cationic surfactants of the present invention are the reaction products of higher fatty acids with a polyamine selected from the group consisting of hydroxyalkylalkylenediamines and dialkylenetriamines and mixtures thereof.
- a preferred component is a nitrogenous compound selected from the group consisting of:
- said reaction product containing a composition having a compound of the formula:
- R is an acyclic aliphatic C ! 5 -C 21 hydrocarbon group and R, and R 3 are divalent C
- Another preferred component is a cationic nitrogenous salt containing one long chain acyclic aliphatic C ⁇ -C,, hydrocarbon group selected from the group consisting of
- R is an acyclic aliphatic C ⁇ -C,, Hydrocarbon group.
- R ⁇ and R ⁇ are C r C 4 saturated alky l or hydroxyalkyl groups, and A [-] is an anion. especially as described in more detail hereinafter, examples of these surfactants are sold by Witco Chemical Company under the Adogen trademarks; (ii) substituted imidazolinium salts having the formula:
- R is an acyclic aliphatic C 15 -C 21 hydrocarbon group
- R 7 is a hydrogen or a C C 4 saturated alkyl or hydroxyalkyl group
- a [-] is an anion
- R is a C r C 3 alkyl group and R,.
- R and A [-] are as defined above; an example of which is commercially available under the Monaquat ISIES trademark from Mona Industries. Inc.: (iv) alkylpyridihium salts having the formula:
- R is an acyclic aliphatic C I 6 -C 22 hydrocarbon group and A [-] is an anion; and (v) alkanamide alkylene pyridinium salts having the formula: wherein R, is an acyclic aliphatic C ⁇ -C,, hydrocarbon group, R, is a divalent C,-C 3 alkylene group, and A [-] is an ion group; and mixtures thereof.
- 5 -C 2 , hydrocarbon groups or one said group and an arylalkyl group are selected from the group consisting of:
- each R 4 is an acyclic aliphatic C, 5 -C,, hydrocarbon group.
- R is a C r C 4 saturated alkyl or hydroxyalkyl group.
- R g is selected from the group consisting of R 4 and R 5 groups, and
- a [-] is an anion defined as above; examples of which are commercially available from Witco Company under the Adogen trademarks: (ii) diamido quaternary ammonium salts having the formula: O R, O
- each R is an acyclic aliphatic C 1 -C 2) hydrocarbon group
- R is a divalent alkylene group having 1 to 3 "carbon atoms.
- R 5 and Rg are C,-C 4 saturated alkyl or hydroxyalkyl groups, and
- a [-] is an anion; examples of which are sold by Witco Chemical Company under the Varisoft trademark; (iii) diamino alkoxylated quaternary ammonium salts having the formula:
- n is equal to 1 to about 5. and R,. R,. R 5 and A [-] are as defined above;
- each R is an acyclic aliphatic C I 5 -C 2 , hydrocarbon group, each R 5 is a C
- each R ⁇ s an acyclic aliphatic C, ⁇ -C 1 hydrocarbon group.
- R is a divalent alkylene group having 1 to 3 carbon atoms, and R, and A [-] are as defined above, examples are commercially available from Witco Chemical Company under the Varisoft 475 and Varisoft 445 trademarks, and (vi) substituted imidazolinium salts having the formula
- the more preferred cationic conventional surfactant is selected from the group consisting of an alkyltnmethylammonium salt, a dialkyldimethylammonium salt, an alkyldimethylbenzylammonium salt, an alkylpy ⁇ dinium salt, an alkylisoquinohnium salt, benzethonium chloride, and an acylamino acid cationic surfactant
- the anion A [-] provides electrical neutrality
- the anion used to provide electrical neutrality in these salts is a hahde. such as chlonde. bromide, or iodide
- other anions can be used, such as methylsulfate. ethylsulfate. acetate, formate, sulfate. carbonate, and the like Chloride and methylsulfate are preferred herein as anion A
- Cationic surfactants are commonh employed as fabric softeners in
- imidazolinium salts have been used by themselves or in combination with other agents in the treatment of fabrics as disclosed by U.S. Patent No. 4.127.489. Pracht. et al.. incorporated herein by reference in its entirety.
- U.S. Patent No. 2,874.074. Johnson discloses using imidazolinium salts to condition fabrics; and U.S. Patent No.3.681,241. Rudy, and U.S. Patent No. 3,033.704, Sherrill et al. disclose
- Amphoteric Surfactants have a positive or negative charge or both on the
- hydrophilic part of the molecule in acidic or alkaline media hydrophilic part of the molecule in acidic or alkaline media.
- amphoteric surfactants examples include:
- amphoteric surfactants include the alkali metal, alkaline earth metal, ammonium or substituted ammonium salts of alkyl amphocarboxyglycinates and alkyl amphocarboxypropionates. alkyl amphodipropionates. alkyl amphodiacetates. alkyl amphoglycinates and alkyl amphopropionates wherein alkyl represents an alkyl group having 6 to 20 carbon atoms.
- suitable amphoteric surfactants include alkyliminopropionates.
- alkyl iminodipropionates and alkyl amphopropylsulfonates having between 12 and 18 carbon atoms
- alkylbetaines and amidopropylbetaines and alkylsultaines and alkylamidopropylhydroxy sultaines wherein alkyl represents an alkyl group having 6 to 20 carbon atoms are especially preferred.
- amphoteric surfactants include both mono and dicarboxvlates such as those of the formulae:
- R is an alkyl group of 6-20 carbon atoms
- x is 1 or 2
- M is hydrogen or sodium. Mixtures of the above structures are particularly preferred.
- amphoteric surfactants include the following: Alkyl betaines
- R is an alkyl group of 6-20 carbon atoms and M is hydrogen or sodium.
- amphoteric surfactants particularly preferred are the alkali salts of alkyl amphocarboxyglycinates and alkyl amphocarboxypropionates. alk> 1 amphodipropionates. alkyl amphodiacetates. alkyl amphoglycinates. alky 1 amphopropyl sulfonates and alkyl amphopropionates wherein alkyl represents an 1 group having 6 to 20 carbon atoms. Even more preferred are compounds wherein the alkyl group is derived from coconut oil or is a lauryl group, for example, cocoamphodipropionate. Such cocoamphodipropionate surfactants are commercially sold under the trademarks Miranol C2M-SF CONC. and Miranol FBS by Rhone -
- Poulenc Inc. and include:
- cocoamphoacetate (sold under the trademarks MIRANOL CM CONC. and MIRAPON FA), cocoamphopropionate (sold under the trademarks MIRANOL CM-SF CONC. and MIRAPON FAS).
- cocoamphodiacetate (sold under the trademarks MIRANOL C2M CONC. and MIRAPON FB), lauroamphoacetate (sold under the trademarks MIRANOL HM CONC. and MIRAPON LA), lauroamphodiacetate (sold under the trademarks MIRANOL H2M CONC. and MIRAPON LB), lauroamphodipropionate (sold under the trademarks MIRANOL H2M SF CONC. AND MIRAPON LBS).
- lauroamphodiacetate obtained from a mixture of lauric and myristic acids (sold under the trademark MIRANOL BM CONC). and cocoamphopropyl sulfonate (sold under the trademark MIRANOL CS CONC.)
- caproamphoacetate sold under the trademark MIRANOL SM CONC.
- stearoamphoacetate sold under the trademark MIRANOL DM.
- the aqueous surfactant compositions of the invention comprise a concentration of surfactant equal to or less than the cmc of corresponding conventional surfactants assuming that the gemini is represented in the conventional surfactants as a surfactant having only one hydrophobic grouping and one hydrophilic grouping corresponding to those in the gemini surfactant.
- the total surfactant loading is equal to or less than 80% and more preferably equal to or-less than 60% of the cmc of the conventional surfactants in the final use area.
- the total aqueous surfactant concentration at end-use level is less than or equal to about 0.01 % total surfactant on an active basis, preferably less than about or equal to 0.008%.
- gemini surfactant ranges from 100% to about 10%. preferably from 100% to about 20% and more preferably from 100% to about 35% of the total active surfactant in the end-use compositions.
- the remainder of the surfactant actives comprise other surfactants not claimed under the term "gemini surfactants" including conventional and other
- surfactant compositions comprising: 1 ) from about 10% to about 100% by weight of nonionic. cationic. anionic. or amphoteric gemini surfactants or a combination thereof : and
- Detergent compositions prepared utilizing the instant surfactant compositions can be used in laundering processes by forming dilute aqueous solutions of the detergent compositions containing said surfactant compositions and agitating same with soiled fabrics.
- the surfactant compositions of the instant invention can be used in detergent compositions at from about 0.5% to about 80%, preferably from about 2% to about 50% by weight. based on the total weight of the detergent composition.
- auxiliary additives e.g.. inorganic salts such as Glauber salt and common salt, builders, humectants. solubilizing agents. UV absorbers, pH adjusting agents, softeners, soil release polymers, soil anti-redeposition agents, conditioning polymers (cationic) for hair and fabric softening, chelating agents, and viscosity modifiers may be added to the surfactant compositions of the invention to form the detergent compositions as the ultimate end-use aqueous surfactant/composition requires.
- auxiliary additives e.g... inorganic salts such as Glauber salt and common salt, builders, humectants. solubilizing agents.
- UV absorbers, pH adjusting agents, softeners, soil release polymers, soil anti-redeposition agents, conditioning polymers (cationic) for hair and fabric softening, chelating agents, and viscosity modifiers may be added to the surfactant compositions of the invention to form the detergent compositions as the ultimate end-use aque
- Such detergent compositions provide excellent detergency at very low surfactant use concentrations, and can be formulated to provide different sudsing patterns by varying the amounts and types of the gemini surfactants used and the nature of the other anionic and nonionic surfactants present.
- the gemini surfactants of the invention are extremely mild and non-irritating to both eyes and skin and exhibit low toxicity; enhanced wetting speed, greater surface tension reduction, low and high foaming profile depending on the gemini used, and foam stabilization properties. They also provide excellent compatibility with other surfactants.
- the products of the invention are stable over a wide pH range and are biodegradable. These properties make these surfactants adaptable for use in products ranging from cosmetics to industrial applications, such as for non-irritating shampoos, e.g., baby shampoos, body shampoos, bubble baths, bath gels, hair conditioning gels, lotions, skin creams, make up removal creams, detergents, fabric softeners and other washing and cosmetic products that contact the skin.
- the surfactants of the invention can also find use as hard surface cleaners including cars, dishes, toilets, floors, and the like; laundry detergents and soaps; metal working aids; and the like.
- Oil-in-water emulsions are prepared using the following formulation of 10% mineral oil. about 90% water and 0.01 % surfactant active (based on water phase).
- the coarse emulsions are prepared by vortex mixing each composition for 30 seconds.
- Each emulsion is characterized by droplet size using an optical microscope, the smaller average droplet size indicating a greater degree of emulsification. Stability is determined by the degree of separation of oil at 23°C respectively, the lower the
- EXAMPLE 3 The oil-in-water emulsions are prepared using a formulation of 65% mineral oil. about 35% water and 0.028% surfactant active (based on water). The emulsions are prepared by blending in a rotor-stator type mixer (2000 rpm) for 3 min. Emulsions are characterized by droplet size using an optical microscope and stability by degree of separation of oil at 23 °C respectively. The results are reported in Table 3 as follows:
- Amphoteric and cationic gemini surfactants are used as emulsifiers for mineral oil and compared to corresponding conventional surfactants. The results are shown in Table 4.
- Table 7 shows the detergency with dust-sebum It can be seen that gemini surfactant shows no significant advantage over the traditional surfactants at 0.02% surfactant use concentration, and especially lower performance on polyester fabric. However, gemini surfactants compositions of the invention show a significant advantage over the traditional detergent blend on dust-sebum cotton detergency at 0.01%) usage levels, and this trend is more obvious at the even lower level, 0.005%.
- the gemini surfactant can be also blended with conventional anionic and nonionic surfactants to enhance the detergency of the mixture.
- the surfactants compared are a 3/3/2 ratio blend of polyoxyethylene (7.5) octylphenol (OP), sodium dodecylbenzene sulfonate (LAS), and polyoxyethylene ( 13) methylene bis(octylphenol) (MBOP). This enhanced performance is shown in Table 10, in which the total surfactant content is kept at 0.005%.
- the wash condition is: 150 ppm hard water. 57 ppm triethanolamine/ monoethanolamine (1/1 ) and 37.8°C
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US72643996A | 1996-10-04 | 1996-10-04 | |
US726439 | 1996-10-04 | ||
PCT/IB1997/001230 WO1998015345A1 (en) | 1996-10-04 | 1997-10-06 | Detergent compositions containing low concentration levels of gemini surfactants |
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DE19724897A1 (de) * | 1997-06-12 | 1998-12-17 | Henkel Kgaa | Tensidgemisch und Reinigungsmittel mit Gemini-Tensiden |
CA2328872A1 (en) | 1998-04-22 | 1999-10-28 | Hercules Incorporated | Paper size dispersions |
CN106606992A (zh) * | 2015-10-21 | 2017-05-03 | 南京理工大学 | 非对称型双子咪唑表面活性剂及其制备方法 |
CN106497703A (zh) * | 2016-10-31 | 2017-03-15 | 佛山市南海东方澳龙制药有限公司 | 一种养殖场用含双子表面活性剂的清洗剂及其制备方法 |
US20210163813A1 (en) * | 2017-12-18 | 2021-06-03 | Dow Global Technologies Llc | Ethyleneamine sulfonate-based surfactant for high temperature foaming |
PT3935064T (pt) | 2019-03-06 | 2024-02-06 | Greentech Global Pte Ltd | Dispersões líquidas para halogenetos de acilo |
CN110523539A (zh) * | 2019-08-14 | 2019-12-03 | 江西理工大学 | 一种新型表面活性剂在铝土矿反浮选上的应用方法 |
JP2023509452A (ja) | 2020-01-03 | 2023-03-08 | バーグ エルエルシー | がんを処置するためのube2kモジュレータとしての多環式アミド |
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BE795961A (fr) * | 1972-02-25 | 1973-08-27 | Hoechst Ag | Application d'hemi-esters sulfuriques a la dispersion de colorants |
DE3104991A1 (de) * | 1981-02-12 | 1982-08-19 | Hoechst Ag, 6000 Frankfurt | Anionische grenzflaechenaktive verbindungen auf basis oxalkylierter naphthol-novolake und deren verwendung |
US5160450A (en) * | 1990-12-05 | 1992-11-03 | Lion Corporation | Surface-active agents having two hydrophobic chains and two hydrophilic groups |
WO1995019955A1 (en) * | 1994-01-25 | 1995-07-27 | The Procter & Gamble Company | Gemini polyether fatty acid amides and their use in detergent compositions |
US5534197A (en) * | 1994-01-25 | 1996-07-09 | The Procter & Gamble Company | Gemini polyhydroxy fatty acid amides |
US5643864A (en) * | 1994-08-19 | 1997-07-01 | Rhone-Poulenc, Inc. | Anionic surfactants having multiple hydrophobic and hydrophilic groups |
US5656586A (en) * | 1994-08-19 | 1997-08-12 | Rhone-Poulenc Inc. | Amphoteric surfactants having multiple hydrophobic and hydrophilic groups |
DE4440328A1 (de) * | 1994-11-11 | 1996-05-15 | Huels Chemische Werke Ag | Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Amiden |
DE4441363A1 (de) * | 1994-11-21 | 1996-05-23 | Huels Chemische Werke Ag | Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf Basis von Di-, Oligo- oder Polyolethern |
DE19505368A1 (de) * | 1995-02-17 | 1996-08-22 | Huels Chemische Werke Ag | Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Dicarbonsäurediamiden |
-
1997
- 1997-10-06 AU AU43930/97A patent/AU4393097A/en not_active Abandoned
- 1997-10-06 WO PCT/IB1997/001230 patent/WO1998015345A1/en not_active Application Discontinuation
- 1997-10-06 EP EP97942138A patent/EP0948393A1/de not_active Withdrawn
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