CA2272139C - Polyoxyalkylene surfactants - Google Patents

Polyoxyalkylene surfactants Download PDF

Info

Publication number: CA2272139C
Authority: CA; Canada
Prior art keywords: ethoxylate; methyl; integer; dimethyl; alkyl
Prior art date: 1996-11-26
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.): Expired - Fee Related

Application number

CA002272139A

Other languages

English (en)

French (fr)

Other versions

CA2272139A1 (en

Inventor

Thomas Anthony Cripe

Daniel Stedman Connor

Phillip Kyle Vinson

James Charles Theophile Roger Burckett-St.Laurent

Kenneth William Willman

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Procter and Gamble Co

Original Assignee

Procter and Gamble Co

Priority date (The priority date 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 date listed.)

1996-11-26

Filing date

1997-11-19

Publication date

2002-12-17

1997-11-19 Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co

1998-06-04 Publication of CA2272139A1 publication Critical patent/CA2272139A1/en

2002-12-17 Application granted granted Critical

2002-12-17 Publication of CA2272139C publication Critical patent/CA2272139C/en

2017-11-19 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000004094 surface-active agent Substances 0.000 title claims abstract description 225
239000000203 mixture Substances 0.000 claims abstract description 414
239000003599 detergent Substances 0.000 claims abstract description 171
125000000217 alkyl group Chemical group 0.000 claims abstract description 168
238000004140 cleaning Methods 0.000 claims abstract description 44
-1 ethoxy, propoxy Chemical group 0.000 claims description 197
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 82
125000004432 carbon atom Chemical group C* 0.000 claims description 77
239000007844 bleaching agent Substances 0.000 claims description 62
102000004190 Enzymes Human genes 0.000 claims description 54
108090000790 Enzymes Proteins 0.000 claims description 54
150000001875 compounds Chemical class 0.000 claims description 52
239000001257 hydrogen Substances 0.000 claims description 45
229910052739 hydrogen Inorganic materials 0.000 claims description 45
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
239000004615 ingredient Substances 0.000 claims description 33
239000003795 chemical substances by application Substances 0.000 claims description 29
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 26
239000012190 activator Substances 0.000 claims description 24
239000002689 soil Substances 0.000 claims description 23
239000003945 anionic surfactant Substances 0.000 claims description 20
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 19
239000002736 nonionic surfactant Substances 0.000 claims description 19
238000004061 bleaching Methods 0.000 claims description 17
238000007046 ethoxylation reaction Methods 0.000 claims description 16
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
AATDUADOOPBKAU-UHFFFAOYSA-N 7-methylpentadecan-1-ol Chemical compound CCCCCCCCC(C)CCCCCCO AATDUADOOPBKAU-UHFFFAOYSA-N 0.000 claims description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
ZNYQHFLBAPNPRC-UHFFFAOYSA-N heptadecan-2-ol Chemical compound CCCCCCCCCCCCCCCC(C)O ZNYQHFLBAPNPRC-UHFFFAOYSA-N 0.000 claims description 4
239000003112 inhibitor Substances 0.000 claims description 4
CRXZDFBSTYFRIG-UHFFFAOYSA-N 10-methylpentadecan-1-ol Chemical compound CCCCCC(C)CCCCCCCCCO CRXZDFBSTYFRIG-UHFFFAOYSA-N 0.000 claims description 3
ZYUUMAFOCZAAJV-UHFFFAOYSA-N 11-methylpentadecan-1-ol Chemical compound CCCCC(C)CCCCCCCCCCO ZYUUMAFOCZAAJV-UHFFFAOYSA-N 0.000 claims description 3
OQVQCQIUBIEKFG-UHFFFAOYSA-N 13-methylhexadecan-1-ol Chemical compound CCCC(C)CCCCCCCCCCCCO OQVQCQIUBIEKFG-UHFFFAOYSA-N 0.000 claims description 3
JWIWHDBXJLJNPH-UHFFFAOYSA-N 13-methylpentadecan-1-ol Chemical compound CCC(C)CCCCCCCCCCCCO JWIWHDBXJLJNPH-UHFFFAOYSA-N 0.000 claims description 3
WQBUQCSTGAHNSM-UHFFFAOYSA-N 14-methylhexadecan-1-ol Chemical compound CCC(C)CCCCCCCCCCCCCO WQBUQCSTGAHNSM-UHFFFAOYSA-N 0.000 claims description 3
COTCQLIJYALEFP-UHFFFAOYSA-N 3-methylhexadecan-1-ol Chemical compound CCCCCCCCCCCCCC(C)CCO COTCQLIJYALEFP-UHFFFAOYSA-N 0.000 claims description 3
HZHCYXMBQIANDP-UHFFFAOYSA-N 3-methylpentadecan-1-ol Chemical compound CCCCCCCCCCCCC(C)CCO HZHCYXMBQIANDP-UHFFFAOYSA-N 0.000 claims description 3
IEODIEWNJHUXPT-UHFFFAOYSA-N 4-methylhexadecan-1-ol Chemical compound CCCCCCCCCCCCC(C)CCCO IEODIEWNJHUXPT-UHFFFAOYSA-N 0.000 claims description 3
USCAIUBWMLHYMF-UHFFFAOYSA-N 4-methylpentadecan-1-ol Chemical compound CCCCCCCCCCCC(C)CCCO USCAIUBWMLHYMF-UHFFFAOYSA-N 0.000 claims description 3
TWCCAMIXDPJNKM-UHFFFAOYSA-N 5-methylhexadecan-1-ol Chemical compound CCCCCCCCCCCC(C)CCCCO TWCCAMIXDPJNKM-UHFFFAOYSA-N 0.000 claims description 3
QLPBYYNKEZROCN-UHFFFAOYSA-N 5-methylpentadecan-1-ol Chemical compound CCCCCCCCCCC(C)CCCCO QLPBYYNKEZROCN-UHFFFAOYSA-N 0.000 claims description 3
QITMGEIDLGSWJI-UHFFFAOYSA-N 6-methylpentadecan-1-ol Chemical compound CCCCCCCCCC(C)CCCCCO QITMGEIDLGSWJI-UHFFFAOYSA-N 0.000 claims description 3
HPGYNPDQRYCFRW-UHFFFAOYSA-N 7-methylhexadecan-1-ol Chemical compound CCCCCCCCCC(C)CCCCCCO HPGYNPDQRYCFRW-UHFFFAOYSA-N 0.000 claims description 3
TUCDQMRJIWBYSN-UHFFFAOYSA-N 8-methylhexadecan-1-ol Chemical compound CCCCCCCCC(C)CCCCCCCO TUCDQMRJIWBYSN-UHFFFAOYSA-N 0.000 claims description 3
OYDBJGVJQMXASR-UHFFFAOYSA-N 8-methylpentadecan-1-ol Chemical compound CCCCCCCC(C)CCCCCCCO OYDBJGVJQMXASR-UHFFFAOYSA-N 0.000 claims description 3
ZMYYAKLNVBDHJK-UHFFFAOYSA-N 9-methylhexadecan-1-ol Chemical compound CCCCCCCC(C)CCCCCCCCO ZMYYAKLNVBDHJK-UHFFFAOYSA-N 0.000 claims description 3
OJHUUXKGMSEIAL-UHFFFAOYSA-N 9-methylpentadecan-1-ol Chemical compound CCCCCCC(C)CCCCCCCCO OJHUUXKGMSEIAL-UHFFFAOYSA-N 0.000 claims description 3
230000007797 corrosion Effects 0.000 claims description 3
238000005260 corrosion Methods 0.000 claims description 3
229920000620 organic polymer Polymers 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
CDSRIXGDJPLOTE-UHFFFAOYSA-N 6-methylhexadecan-1-ol Chemical compound CCCCCCCCCCC(C)CCCCCO CDSRIXGDJPLOTE-UHFFFAOYSA-N 0.000 claims description 2
VWIYQXVJELWBLM-UHFFFAOYSA-N 10-methylhexadecan-1-ol Chemical compound CCCCCCC(C)CCCCCCCCCO VWIYQXVJELWBLM-UHFFFAOYSA-N 0.000 claims 2
BHUSBECOLJTBTA-UHFFFAOYSA-N 11-methylhexadecan-1-ol Chemical compound CCCCCC(C)CCCCCCCCCCO BHUSBECOLJTBTA-UHFFFAOYSA-N 0.000 claims 2
RULGCHAXCANRBL-UHFFFAOYSA-N 12-methylhexadecan-1-ol Chemical compound CCCCC(C)CCCCCCCCCCCO RULGCHAXCANRBL-UHFFFAOYSA-N 0.000 claims 2
CIUGEUVAWSWBTB-UHFFFAOYSA-N 12-methylpentadecan-1-ol Chemical compound CCCC(C)CCCCCCCCCCCO CIUGEUVAWSWBTB-UHFFFAOYSA-N 0.000 claims 2
MVYPKRADYPIKKS-UHFFFAOYSA-N 2,10-dimethylpentadecan-1-ol Chemical compound CCCCCC(C)CCCCCCCC(C)CO MVYPKRADYPIKKS-UHFFFAOYSA-N 0.000 claims 2
HTAKISAXTQLJGM-UHFFFAOYSA-N 2,10-dimethyltetradecan-1-ol Chemical compound CCCCC(C)CCCCCCCC(C)CO HTAKISAXTQLJGM-UHFFFAOYSA-N 0.000 claims 2
SUECHUSKTKVWII-UHFFFAOYSA-N 2,11-dimethylpentadecan-1-ol Chemical compound CCCCC(C)CCCCCCCCC(C)CO SUECHUSKTKVWII-UHFFFAOYSA-N 0.000 claims 2
LOZWNEWHBUXBCA-UHFFFAOYSA-N 2,11-dimethyltetradecan-1-ol Chemical compound CCCC(C)CCCCCCCCC(C)CO LOZWNEWHBUXBCA-UHFFFAOYSA-N 0.000 claims 2
XKCHTVOKIYIWDN-UHFFFAOYSA-N 2,12-dimethylpentadecan-1-ol Chemical compound CCCC(C)CCCCCCCCCC(C)CO XKCHTVOKIYIWDN-UHFFFAOYSA-N 0.000 claims 2
RGYRYZQXUBINQA-UHFFFAOYSA-N 2,12-dimethyltetradecan-1-ol Chemical compound CCC(C)CCCCCCCCCC(C)CO RGYRYZQXUBINQA-UHFFFAOYSA-N 0.000 claims 2
UTJVUJVUBBPPGM-UHFFFAOYSA-N 2,13-dimethylpentadecan-1-ol Chemical compound CCC(C)CCCCCCCCCCC(C)CO UTJVUJVUBBPPGM-UHFFFAOYSA-N 0.000 claims 2
MWNWEQHHASAOEU-UHFFFAOYSA-N 2,3-dimethylpentadecan-1-ol Chemical compound CCCCCCCCCCCCC(C)C(C)CO MWNWEQHHASAOEU-UHFFFAOYSA-N 0.000 claims 2
PEHXXCUSMPZMKS-UHFFFAOYSA-N 2,3-dimethyltetradecan-1-ol Chemical compound CCCCCCCCCCCC(C)C(C)CO PEHXXCUSMPZMKS-UHFFFAOYSA-N 0.000 claims 2
ZYIFYIQWTWPTEJ-UHFFFAOYSA-N 2,4-dimethylpentadecan-1-ol Chemical compound CCCCCCCCCCCC(C)CC(C)CO ZYIFYIQWTWPTEJ-UHFFFAOYSA-N 0.000 claims 2
AVJVDWDELKUAKE-UHFFFAOYSA-N 2,4-dimethyltetradecan-1-ol Chemical compound CCCCCCCCCCC(C)CC(C)CO AVJVDWDELKUAKE-UHFFFAOYSA-N 0.000 claims 2
SDMUDPFAXZEOLC-UHFFFAOYSA-N 2,5-dimethylpentadecan-1-ol Chemical compound CCCCCCCCCCC(C)CCC(C)CO SDMUDPFAXZEOLC-UHFFFAOYSA-N 0.000 claims 2
FKFSERQPKIYIDW-UHFFFAOYSA-N 2,5-dimethyltetradecan-1-ol Chemical compound CCCCCCCCCC(C)CCC(C)CO FKFSERQPKIYIDW-UHFFFAOYSA-N 0.000 claims 2
BJOQVMRLMCFVMF-UHFFFAOYSA-N 2,6-dimethylpentadecan-1-ol Chemical compound CCCCCCCCCC(C)CCCC(C)CO BJOQVMRLMCFVMF-UHFFFAOYSA-N 0.000 claims 2
DRDVHCSNTGTEOH-UHFFFAOYSA-N 2,6-dimethyltetradecan-1-ol Chemical compound CCCCCCCCC(C)CCCC(C)CO DRDVHCSNTGTEOH-UHFFFAOYSA-N 0.000 claims 2
YENWQWYLHJTAQB-UHFFFAOYSA-N 2,7-dimethylpentadecan-1-ol Chemical compound CCCCCCCCC(C)CCCCC(C)CO YENWQWYLHJTAQB-UHFFFAOYSA-N 0.000 claims 2
DLQBSLQQCAVWDT-UHFFFAOYSA-N 2,7-dimethyltetradecan-1-ol Chemical compound CCCCCCCC(C)CCCCC(C)CO DLQBSLQQCAVWDT-UHFFFAOYSA-N 0.000 claims 2
OVFVOONETFEMQT-UHFFFAOYSA-N 2,8-dimethylpentadecan-1-ol Chemical compound CCCCCCCC(C)CCCCCC(C)CO OVFVOONETFEMQT-UHFFFAOYSA-N 0.000 claims 2
GUTMCTKABIVFAX-UHFFFAOYSA-N 2,8-dimethyltetradecan-1-ol Chemical compound CCCCCCC(C)CCCCCC(C)CO GUTMCTKABIVFAX-UHFFFAOYSA-N 0.000 claims 2
KRWVIVSNXFPYJB-UHFFFAOYSA-N 2,9-dimethylpentadecan-1-ol Chemical compound CCCCCCC(C)CCCCCCC(C)CO KRWVIVSNXFPYJB-UHFFFAOYSA-N 0.000 claims 2
HRARMCULBGOAPD-UHFFFAOYSA-N 2,9-dimethyltetradecan-1-ol Chemical compound CCCCCC(C)CCCCCCC(C)CO HRARMCULBGOAPD-UHFFFAOYSA-N 0.000 claims 2
239000007788 liquid Substances 0.000 abstract description 68
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 66
238000000034 method Methods 0.000 abstract description 60
230000008569 process Effects 0.000 abstract description 23
238000009472 formulation Methods 0.000 abstract description 17
235000019441 ethanol Nutrition 0.000 description 95
239000000047 product Substances 0.000 description 80
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 76
150000008051 alkyl sulfates Chemical class 0.000 description 76
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 65
239000000463 material Substances 0.000 description 62
229940088598 enzyme Drugs 0.000 description 52
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 47
238000005406 washing Methods 0.000 description 44
238000006243 chemical reaction Methods 0.000 description 38
229910052757 nitrogen Inorganic materials 0.000 description 38
229920001223 polyethylene glycol Polymers 0.000 description 38
239000003054 catalyst Substances 0.000 description 35
239000011734 sodium Substances 0.000 description 35
239000002202 Polyethylene glycol Substances 0.000 description 32
150000001298 alcohols Chemical class 0.000 description 32
108010065511 Amylases Proteins 0.000 description 31
102000013142 Amylases Human genes 0.000 description 31
239000007791 liquid phase Substances 0.000 description 30
239000002245 particle Substances 0.000 description 30
239000000243 solution Substances 0.000 description 30
150000001412 amines Chemical group 0.000 description 29
235000019418 amylase Nutrition 0.000 description 29
150000003839 salts Chemical class 0.000 description 29
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
229910052708 sodium Inorganic materials 0.000 description 28
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 26
235000014113 dietary fatty acids Nutrition 0.000 description 26
239000000194 fatty acid Substances 0.000 description 26
229930195729 fatty acid Natural products 0.000 description 26
239000004744 fabric Substances 0.000 description 25
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 24
150000002148 esters Chemical class 0.000 description 24
239000012071 phase Substances 0.000 description 24
229920000642 polymer Polymers 0.000 description 23
239000002253 acid Substances 0.000 description 22
229940025131 amylases Drugs 0.000 description 21
229920001296 polysiloxane Polymers 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
108090001060 Lipase Proteins 0.000 description 20
102000004882 Lipase Human genes 0.000 description 20
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 20
230000000694 effects Effects 0.000 description 20
108091005804 Peptidases Proteins 0.000 description 19
239000007859 condensation product Substances 0.000 description 19
229920001577 copolymer Polymers 0.000 description 19
239000003921 oil Substances 0.000 description 19
239000002904 solvent Substances 0.000 description 19
239000004367 Lipase Substances 0.000 description 18
239000003085 diluting agent Substances 0.000 description 18
150000004665 fatty acids Chemical class 0.000 description 18
235000019421 lipase Nutrition 0.000 description 18
235000019198 oils Nutrition 0.000 description 18
150000001336 alkenes Chemical class 0.000 description 17
238000004851 dishwashing Methods 0.000 description 17
150000002191 fatty alcohols Chemical class 0.000 description 17
238000004519 manufacturing process Methods 0.000 description 17
239000010457 zeolite Substances 0.000 description 17
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
239000004365 Protease Substances 0.000 description 16
230000015572 biosynthetic process Effects 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
229910021536 Zeolite Inorganic materials 0.000 description 15
239000000975 dye Substances 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000002304 perfume Substances 0.000 description 15
239000000126 substance Substances 0.000 description 15
239000004382 Amylase Substances 0.000 description 14
125000003342 alkenyl group Chemical group 0.000 description 14
229910052799 carbon Inorganic materials 0.000 description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
150000002430 hydrocarbons Chemical class 0.000 description 14
229920005646 polycarboxylate Polymers 0.000 description 14
229910052700 potassium Inorganic materials 0.000 description 14
238000002360 preparation method Methods 0.000 description 14
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 13
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 13
125000000129 anionic group Chemical group 0.000 description 13
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 13
239000011591 potassium Substances 0.000 description 13
150000003467 sulfuric acid derivatives Chemical class 0.000 description 13
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 12
125000002091 cationic group Chemical group 0.000 description 12
229930195733 hydrocarbon Natural products 0.000 description 12
REIUXOLGHVXAEO-UHFFFAOYSA-N n-pentadecyl alcohol Natural products CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
241000894007 species Species 0.000 description 12
238000003756 stirring Methods 0.000 description 12
238000012546 transfer Methods 0.000 description 12
GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
229910052783 alkali metal Inorganic materials 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
229910052801 chlorine Inorganic materials 0.000 description 11
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 11
230000002209 hydrophobic effect Effects 0.000 description 11
238000004900 laundering Methods 0.000 description 11
239000011236 particulate material Substances 0.000 description 11
239000000843 powder Substances 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Natural products O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 10
150000007513 acids Chemical class 0.000 description 10
238000013019 agitation Methods 0.000 description 10
230000008901 benefit Effects 0.000 description 10
150000007942 carboxylates Chemical group 0.000 description 10
150000001768 cations Chemical class 0.000 description 10
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 10
239000007789 gas Substances 0.000 description 10
239000000178 monomer Substances 0.000 description 10
230000003287 optical effect Effects 0.000 description 10
229920001451 polypropylene glycol Polymers 0.000 description 10
239000000344 soap Substances 0.000 description 10
239000007787 solid Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
150000003863 ammonium salts Chemical class 0.000 description 9
150000001450 anions Chemical class 0.000 description 9
239000002738 chelating agent Substances 0.000 description 9
239000002270 dispersing agent Substances 0.000 description 9
125000002768 hydroxyalkyl group Chemical group 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
150000003138 primary alcohols Chemical class 0.000 description 9
150000004760 silicates Chemical class 0.000 description 9
230000000087 stabilizing effect Effects 0.000 description 9
239000004711 α-olefin Substances 0.000 description 9
HLZKNKRTKFSKGZ-UHFFFAOYSA-N 1-Tetradecanol Natural products CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 8
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 8
108010084185 Cellulases Proteins 0.000 description 8
102000005575 Cellulases Human genes 0.000 description 8
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
DMULVCHRPCFFGV-UHFFFAOYSA-N N,N-dimethyltryptamine Chemical compound C1=CC=C2C(CCN(C)C)=CNC2=C1 DMULVCHRPCFFGV-UHFFFAOYSA-N 0.000 description 8
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DAPMZWDGZVFZMK-UHFFFAOYSA-N sodium;2-[2-[4-[4-[2-(2-sulfophenyl)ethenyl]phenyl]phenyl]ethenyl]benzenesulfonic acid Chemical group [Na].[Na].OS(=O)(=O)C1=CC=CC=C1C=CC1=CC=C(C=2C=CC(C=CC=3C(=CC=CC=3)S(O)(=O)=O)=CC=2)C=C1 DAPMZWDGZVFZMK-UHFFFAOYSA-N 0.000 description 1
KQHKITXZJDOIOD-UHFFFAOYSA-M sodium;3-sulfobenzoate Chemical compound [Na+].OS(=O)(=O)C1=CC=CC(C([O-])=O)=C1 KQHKITXZJDOIOD-UHFFFAOYSA-M 0.000 description 1
QEKATQBVVAZOAY-UHFFFAOYSA-M sodium;4-propan-2-ylbenzenesulfonate Chemical compound [Na+].CC(C)C1=CC=C(S([O-])(=O)=O)C=C1 QEKATQBVVAZOAY-UHFFFAOYSA-M 0.000 description 1
MWZFQMUXPSUDJQ-KVVVOXFISA-M sodium;[(z)-octadec-9-enyl] sulfate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCOS([O-])(=O)=O MWZFQMUXPSUDJQ-KVVVOXFISA-M 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
125000003696 stearoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004079 stearyl 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])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])[H] 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
230000001629 suppression Effects 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
229940116411 terpineol Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000004685 tetrahydrates Chemical class 0.000 description 1
MSLRPWGRFCKNIZ-UHFFFAOYSA-J tetrasodium;hydrogen peroxide;dicarbonate Chemical compound [Na+].[Na+].[Na+].[Na+].OO.OO.OO.[O-]C([O-])=O.[O-]C([O-])=O MSLRPWGRFCKNIZ-UHFFFAOYSA-J 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
101150014006 thrA gene Proteins 0.000 description 1
239000010936 titanium Substances 0.000 description 1
CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
125000005591 trimellitate group Chemical group 0.000 description 1
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
JXVGWAIUCIHLLC-UHFFFAOYSA-K trisodium 2-hydroxypropane-1,2,3-tricarboxylate 2-hydroxypropane-1,2,3-tricarboxylic acid dihydrate Chemical compound O.O.[Na+].[Na+].[Na+].OC(=O)CC(O)(CC(O)=O)C(O)=O.OC(CC([O-])=O)(CC([O-])=O)C([O-])=O JXVGWAIUCIHLLC-UHFFFAOYSA-K 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
210000001364 upper extremity Anatomy 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
239000003643 water by type Substances 0.000 description 1
230000002087 whitening effect Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
FUQAYSQLAOJBBC-PAPYEOQZSA-N β-caryophyllene alcohol Chemical compound C1C[C@](C2)(C)CCC[C@]2(O)[C@H]2CC(C)(C)[C@@H]21 FUQAYSQLAOJBBC-PAPYEOQZSA-N 0.000 description 1

Classifications

- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Organic Chemistry (AREA)
Detergent Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

CA002272139A 1996-11-26 1997-11-19 Polyoxyalkylene surfactants Expired - Fee Related CA2272139C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US3191796P	1996-11-26	1996-11-26
US60/031,917		1996-11-26
PCT/US1997/021160 WO1998023712A2 (en)	1996-11-26	1997-11-19	Polyoxyalkylene surfactants

Publications (2)

Publication Number	Publication Date
CA2272139A1 CA2272139A1 (en)	1998-06-04
CA2272139C true CA2272139C (en)	2002-12-17

Family

ID=21862096

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002272139A Expired - Fee Related CA2272139C (en)	1996-11-26	1997-11-19	Polyoxyalkylene surfactants

Country Status (11)

Country	Link
EP (1)	EP0944699A2 (es)
JP (2)	JP4364308B2 (es)
CN (2)	CN100457880C (es)
AR (1)	AR011769A1 (es)
BR (1)	BR9713301A (es)
CA (1)	CA2272139C (es)
CZ (1)	CZ302716B6 (es)
HU (1)	HUP0001842A3 (es)
MA (1)	MA24408A1 (es)
TR (1)	TR199901159T2 (es)
WO (1)	WO1998023712A2 (es)

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EG21174A (en) *	1996-04-16	2000-12-31	Procter & Gamble	Surfactant manufacture
PH11997056158B1 (en) *	1996-04-16	2001-10-15	Procter & Gamble	Mid-chain branched primary alkyl sulphates as surfactants
MA24137A1 (fr)	1996-04-16	1997-12-31	Procter & Gamble	Fabrication d'agents de surface ramifies .
US6093856A (en) *	1996-11-26	2000-07-25	The Procter & Gamble Company	Polyoxyalkylene surfactants
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CN1187036C (zh)	1997-10-14	2005-02-02	普罗克特和甘保尔公司	含有中链支化表面活性剂的个人清洁组合物
EP1023426B1 (en)	1997-10-14	2005-02-09	The Procter & Gamble Company	Light-duty liquid or gel dishwashing detergent compositions comprising mid-chain branched surfactants
CN1281499A (zh)	1997-10-14	2001-01-24	普罗格特-甘布尔公司	含有中链支链表面活性剂的颗粒洗涤剂组合物
WO1999064552A1 (en) *	1998-06-10	1999-12-16	The Procter & Gamble Company	Detergent compositions comprising a mannanase and a mid-branched anionic surfactant
US7202205B1 (en)	1999-09-01	2007-04-10	Daniel Stedman Connor	Processes for making surfactants via adsorptive separation and products thereof
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GB0123382D0 (en) *	2001-09-28	2001-11-21	Unilever Plc	Water soluble package and liquid contents thereof
CA2425618C (en) *	2002-04-17	2007-10-23	Nippon Shokubai Co., Ltd.	Specific polymer-compounded detergent composition
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EP2650275A1 (en) *	2008-09-22	2013-10-16	The Procter & Gamble Company	Specific polybranched alcohols and consumer products based thereon
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CN102995468B (zh) *	2012-11-26	2015-04-15	浙江安诺其助剂有限公司	一种涤纶织物染色除油剂及其制备方法
JP6052777B2 (ja) *	2012-12-26	2016-12-27	花王株式会社	液体洗浄剤組成物
JP6207084B2 (ja) *	2014-06-25	2017-10-04	ライオン株式会社	食器洗い用液体洗浄剤
US9493725B2 (en) *	2014-09-08	2016-11-15	The Procter & Gamble Company	Detergent compositions containing a predominantly C15 alkyl branched surfactant
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US11292002B2 (en)	2016-04-08	2022-04-05	The Governing Council Of The University Of Toronto	Surfactant additives for digital microfluidic devices for high protein content droplets transport
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1997
- 1997-11-19 EP EP97948391A patent/EP0944699A2/en not_active Withdrawn
- 1997-11-19 CZ CZ0186899A patent/CZ302716B6/cs not_active IP Right Cessation
- 1997-11-19 CN CNB021475083A patent/CN100457880C/zh not_active Expired - Fee Related
- 1997-11-19 CN CN97181417A patent/CN1120226C/zh not_active Expired - Fee Related
- 1997-11-19 CA CA002272139A patent/CA2272139C/en not_active Expired - Fee Related
- 1997-11-19 BR BR9713301A patent/BR9713301A/pt not_active IP Right Cessation
- 1997-11-19 JP JP52472898A patent/JP4364308B2/ja not_active Expired - Fee Related
- 1997-11-19 TR TR1999/01159T patent/TR199901159T2/xx unknown
- 1997-11-19 WO PCT/US1997/021160 patent/WO1998023712A2/en not_active Ceased
- 1997-11-19 HU HU0001842A patent/HUP0001842A3/hu unknown
- 1997-11-25 MA MA24875A patent/MA24408A1/fr unknown
- 1997-11-26 AR ARP970105555A patent/AR011769A1/es unknown
2006
- 2006-09-07 JP JP2006243135A patent/JP2007016246A/ja active Pending

Also Published As

Publication number	Publication date
BR9713301A (pt)	2000-03-21
MA24408A1 (fr)	1998-07-01
JP2007016246A (ja)	2007-01-25
CN1441042A (zh)	2003-09-10
WO1998023712A3 (en)	1998-07-23
EP0944699A2 (en)	1999-09-29
CA2272139A1 (en)	1998-06-04
HUP0001842A2 (hu)	2000-09-28
CZ302716B6 (cs)	2011-09-21
AR011769A1 (es)	2000-09-13
HUP0001842A3 (en)	2001-02-28
JP2001506679A (ja)	2001-05-22
WO1998023712A2 (en)	1998-06-04
JP4364308B2 (ja)	2009-11-18
CN100457880C (zh)	2009-02-04
CZ186899A3 (cs)	2000-04-12
CN1244892A (zh)	2000-02-16
TR199901159T2 (xx)	1999-08-23
CN1120226C (zh)	2003-09-03

Publication	Publication Date	Title
CA2272139C (en)	2002-12-17	Polyoxyalkylene surfactants
US6093856A (en)	2000-07-25	Polyoxyalkylene surfactants
AU727554B2 (en)	2000-12-14	Mid-chain branched primary alkyl sulphates as surfactants
US6008181A (en)	1999-12-28	Mid-Chain branched Alkoxylated Sulfate Surfactants
AU727909B2 (en)	2001-01-04	Mid-chain branched surfactants
US6015781A (en)	2000-01-18	Detergent compositions containing selected mid-chain branched surfactants
US6242406B1 (en)	2001-06-05	Mid-chain branched surfactants with cellulose derivatives
AU742227B2 (en)	2001-12-20	Mixed surfactant system
AU741462B2 (en)	2001-11-29	Granular detergent compositions comprising mid-chain branched surfactants
CA2252362C (en)	2002-02-26	Detergent compositions containing selected mid-chain branched surfactants
CA2305330A1 (en)	1999-04-22	Mid-chain branched surfactants with cellulose derivatives
CA2305467A1 (en)	1999-04-22	Mid-chain branched surfactants with potassium ions

Legal Events

Date	Code	Title	Description
1999-05-17	EEER	Examination request
2013-12-31	MKLA	Lapsed	Effective date: 20131119