AU682835B2 - Alkylidene glycerol surfactants and detergent compositions containing them - Google Patents

Alkylidene glycerol surfactants and detergent compositions containing them

Info

Publication number: AU682835B2
Authority: AU; Australia
Prior art keywords: detergent composition; compound; cosurfactant; diglycerol; surfactant
Prior art date: 1992-11-25
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.): Ceased

Application number

AU55623/94A

Other languages

English (en)

Other versions

AU5562394A (en

Inventor

Robert John Crawford

Richard John Curtis

Abid Nadin Khan-Lodhi

Malcolm Philip Nicholls

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.)

Unilever PLC

Original Assignee

Unilever PLC

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.)

1992-11-25

Filing date

1993-11-17

Publication date

1997-10-23

1992-11-25 Priority claimed from US07/981,737 external-priority patent/US5389279A/en

1993-09-21 Priority claimed from GB939319462A external-priority patent/GB9319462D0/en

1993-11-17 Application filed by Unilever PLC filed Critical Unilever PLC

1994-06-22 Publication of AU5562394A publication Critical patent/AU5562394A/en

1997-10-23 Application granted granted Critical

1997-10-23 Publication of AU682835B2 publication Critical patent/AU682835B2/en

2013-11-17 Anticipated expiration legal-status Critical

Status Ceased legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims description 67
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims description 47
239000003599 detergent Substances 0.000 title claims description 40
239000004094 surface-active agent Substances 0.000 title claims description 36
-1 Alkylidene glycerol Chemical compound 0.000 title description 80
150000001875 compounds Chemical class 0.000 claims description 46
239000007788 liquid Substances 0.000 claims description 22
GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical group OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 17
239000002736 nonionic surfactant Substances 0.000 claims description 17
239000004064 cosurfactant Substances 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
229910021653 sulphate ion Inorganic materials 0.000 claims description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
239000003945 anionic surfactant Substances 0.000 claims description 3
125000002347 octyl 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])[H] 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
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 description 2
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 claims description 2
150000003138 primary alcohols Chemical group 0.000 claims description 2
239000000080 wetting agent Substances 0.000 claims description 2
125000006538 C11 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])* 0.000 claims 1
150000001299 aldehydes Chemical class 0.000 claims 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims 1
239000007844 bleaching agent Substances 0.000 description 19
235000011187 glycerol Nutrition 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 11
PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 11
239000000463 material Substances 0.000 description 11
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 11
229940117972 triolein Drugs 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000010457 zeolite Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
229910021536 Zeolite Inorganic materials 0.000 description 8
125000001118 alkylidene group Chemical group 0.000 description 8
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 8
239000002243 precursor Substances 0.000 description 8
239000002689 soil Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
235000014113 dietary fatty acids Nutrition 0.000 description 7
239000004744 fabric Substances 0.000 description 7
239000000194 fatty acid Substances 0.000 description 7
229930195729 fatty acid Natural products 0.000 description 7
229920000642 polymer Polymers 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000000344 soap Substances 0.000 description 7
AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
238000005406 washing Methods 0.000 description 6
150000001241 acetals Chemical class 0.000 description 5
150000004665 fatty acids Chemical class 0.000 description 5
125000000864 peroxy group Chemical group O(O*)* 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
XSVSPKKXQGNHMD-UHFFFAOYSA-N 5-bromo-3-methyl-1,2-thiazole Chemical compound CC=1C=C(Br)SN=1 XSVSPKKXQGNHMD-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000004115 Sodium Silicate Substances 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
229910000323 aluminium silicate Inorganic materials 0.000 description 4
239000012267 brine Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 description 4
239000012259 ether extract Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229940045872 sodium percarbonate Drugs 0.000 description 4
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 4
229910052911 sodium silicate Inorganic materials 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
239000002904 solvent Substances 0.000 description 4
230000002195 synergetic effect Effects 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
SUDGIPZELPUBSS-UHFFFAOYSA-N 4-undecylheptane-1,2,3,5,6,7-hexol Chemical class CCCCCCCCCCCC(C(O)C(O)CO)C(O)C(O)CO SUDGIPZELPUBSS-UHFFFAOYSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229920006243 acrylic copolymer Polymers 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000005187 foaming Methods 0.000 description 3
238000010348 incorporation Methods 0.000 description 3
239000002304 perfume Substances 0.000 description 3
229920005996 polystyrene-poly(ethylene-butylene)-polystyrene Polymers 0.000 description 3
239000000047 product Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
LSKONYYRONEBKA-UHFFFAOYSA-N 2-Dodecanone Chemical compound CCCCCCCCCCC(C)=O LSKONYYRONEBKA-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
229940120146 EDTMP Drugs 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
BGRWYDHXPHLNKA-UHFFFAOYSA-N Tetraacetylethylenediamine Chemical compound CC(=O)N(C(C)=O)CCN(C(C)=O)C(C)=O BGRWYDHXPHLNKA-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000012190 activator Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
239000004411 aluminium Substances 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
238000004061 bleaching Methods 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000001860 citric acid derivatives Chemical class 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000004851 dishwashing Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 2
230000007613 environmental effect Effects 0.000 description 2
229940071106 ethylenediaminetetraacetate Drugs 0.000 description 2
150000002314 glycerols Chemical class 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
229920000058 polyacrylate Polymers 0.000 description 2
229920005646 polycarboxylate Polymers 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
239000011253 protective coating Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000000526 short-path distillation Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 2
CIOXZGOUEYHNBF-UHFFFAOYSA-N (carboxymethoxy)succinic acid Chemical class OC(=O)COC(C(O)=O)CC(O)=O CIOXZGOUEYHNBF-UHFFFAOYSA-N 0.000 description 1
NCRNCSZWOOYBQF-UHFFFAOYSA-N 1,1-Dimethoxydecane Chemical compound CCCCCCCCCC(OC)OC NCRNCSZWOOYBQF-UHFFFAOYSA-N 0.000 description 1
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
CFPOJWPDQWJEMO-UHFFFAOYSA-N 2-(1,2-dicarboxyethoxy)butanedioic acid Chemical class OC(=O)CC(C(O)=O)OC(C(O)=O)CC(O)=O CFPOJWPDQWJEMO-UHFFFAOYSA-N 0.000 description 1
LVVZBNKWTVZSIU-UHFFFAOYSA-N 2-(carboxymethoxy)propanedioic acid Chemical class OC(=O)COC(C(O)=O)C(O)=O LVVZBNKWTVZSIU-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
AJUWUYJULVYGRA-UHFFFAOYSA-N Dodecanal dimethyl acetal Chemical compound CCCCCCCCCCCC(OC)OC AJUWUYJULVYGRA-UHFFFAOYSA-N 0.000 description 1
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 1
JYXGIOKAKDAARW-UHFFFAOYSA-N N-(2-hydroxyethyl)iminodiacetic acid Chemical class OCCN(CC(O)=O)CC(O)=O JYXGIOKAKDAARW-UHFFFAOYSA-N 0.000 description 1
SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910021538 borax Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
MMCOUVMKNAHQOY-UHFFFAOYSA-N carbonoperoxoic acid Chemical compound OOC(O)=O MMCOUVMKNAHQOY-UHFFFAOYSA-N 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003974 emollient agent Substances 0.000 description 1
238000007046 ethoxylation reaction Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000004088 foaming agent Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008233 hard water Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052816 inorganic phosphate Inorganic materials 0.000 description 1
230000002366 lipolytic effect Effects 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-L maleate(2-) Chemical compound [O-]C(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-L 0.000 description 1
238000002156 mixing Methods 0.000 description 1
WKGHJBXTMFXUNA-UHFFFAOYSA-N n,n,n',n'-tetrahexadecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCC)CCN(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC WKGHJBXTMFXUNA-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
125000005342 perphosphate group Chemical group 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002797 proteolythic effect Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
239000003352 sequestering agent Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000004328 sodium tetraborate Substances 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
235000019832 sodium triphosphate Nutrition 0.000 description 1
IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 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
AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000008096 xylene Substances 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
- C11D1/83—Mixtures of non-ionic with anionic 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
- C11D1/662—Carbohydrates or derivatives
- 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
- C11D1/825—Mixtures of compounds all of which are non-ionic
- 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
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0004—Non aqueous liquid compositions comprising insoluble particles
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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

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)
Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Detergent Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

AU55623/94A 1992-11-25 1993-11-17 Alkylidene glycerol surfactants and detergent compositions containing them Ceased AU682835B2 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US07/981,737 US5389279A (en)	1991-12-31	1992-11-25	Compositions comprising nonionic glycolipid surfactants
US981737		1992-11-25
GB9319462		1993-09-21
GB939319462A GB9319462D0 (en)	1992-11-25	1993-09-21	Alkylidene glycerol surfactants and detergent compositions containing them
PCT/EP1993/003170 WO1994012489A1 (en)	1992-11-25	1993-11-17	Alkylidene glycerol surfactants and detergent compositions containing them

Publications (2)

Publication Number	Publication Date
AU5562394A AU5562394A (en)	1994-06-22
AU682835B2 true AU682835B2 (en)	1997-10-23

Family

ID=26303551

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU55623/94A Ceased AU682835B2 (en)	1992-11-25	1993-11-17	Alkylidene glycerol surfactants and detergent compositions containing them

Country Status (7)

Country	Link
EP (1)	EP0670834B1 (ja)
JP (1)	JP2848706B2 (ja)
AU (1)	AU682835B2 (ja)
BR (1)	BR9307517A (ja)
DE (1)	DE69308883T2 (ja)
ES (1)	ES2100664T3 (ja)
WO (1)	WO1994012489A1 (ja)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10042514A1 (de) *	2000-08-30	2002-03-14	Clariant Gmbh	Wässerige Flüssigkeiten enthaltend ein Tensid und ein Acetal
DE10232780A1 (de) *	2002-07-18	2004-02-12	Basf Ag	Co-Tenside auf Basis von Aldehyden
EP1954140B1 (en)	2005-11-22	2013-05-29	Segetis, Inc.	Glycerol levulinate ketals and their use
BRPI0818370A2 (pt)	2007-10-09	2017-05-16	Segetis Inc	métodos de fabricar cetais e acetais
WO2010036884A1 (en)	2008-09-25	2010-04-01	Segetis, Inc.	Ketal ester derivatives
BRPI1013943B1 (pt)	2009-06-22	2020-03-17	Segetis, Inc.	Composto, método para sintetizar o mesmo, composição e composição lubrificante
AU2011250962B2 (en)	2010-05-10	2015-09-03	Gfbiochemicals Limited	Personal care formulations containing alkyl ketal esters and methods of manufacture
BR112013000575A2 (pt)	2010-08-03	2016-07-05	Segetis Inc	métodos para a fabricação de acetais e cetais, e acetais e cetais produzidos por este meio
WO2012021824A2 (en)	2010-08-12	2012-02-16	Segetis, Inc.	Carboxy ester ketal removal compositions, methods of manufacture, and uses thereof
US9074065B2 (en)	2010-08-12	2015-07-07	Segetis, Inc.	Latex coating compositions including carboxy ester ketal coalescents, methods of manufacture, and uses thereof
EP2613760A2 (en)	2010-09-07	2013-07-17	Segetis, Inc.	Compositions for dyeing keratin fibers
WO2012037122A2 (en)	2010-09-13	2012-03-22	Segetis, Inc.	Fabric softener compositions and methods of manufacture thereof
WO2012054505A2 (en)	2010-10-18	2012-04-26	Segetis, Inc.	Water reducible coating compositions including carboxy ester ketals, methods of manufacture, and uses thereof
JP5832930B2 (ja) *	2012-02-20	2015-12-16	三洋化成工業株式会社	外用組成物
US9458414B2 (en)	2012-09-21	2016-10-04	Gfbiochemicals Limited	Cleaning, surfactant, and personal care compositions
JP2016506383A (ja)	2012-11-29	2016-03-03	サジティス・インコーポレイテッド	カルボキシエステルケタール、その製造方法および使用
CN106946840B (zh) *	2017-04-11	2019-05-24	太原理工大学	一种二甘油单缩醛及其制备方法和应用
US20230174895A1 (en) *	2021-12-08	2023-06-08	The Procter & Gamble Company	Glycerol acetal sulfate and sulfonate surfactants

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2541226B2 (ja) *	1987-07-06	1996-10-09	日本油脂株式会社	ポリオキシアルキレン誘導体からなるカルボニル化合物の修飾剤
JP2870119B2 (ja) *	1990-05-08	1999-03-10	日本油脂株式会社	アルケニルポリグリセロールエーテルおよびアルケニルイソプロピリデンポリグリセロールエーテル
EP0510165B1 (fr) *	1990-11-14	1995-01-25	L'oreal	Composes amphiphiles non-ioniques derives du glycerol, leur procede de preparation, composes intermediaires correspondants et compositions contenant lesdits composes

1993
- 1993-11-17 JP JP6512694A patent/JP2848706B2/ja not_active Expired - Lifetime
- 1993-11-17 EP EP94900806A patent/EP0670834B1/en not_active Expired - Lifetime
- 1993-11-17 AU AU55623/94A patent/AU682835B2/en not_active Ceased
- 1993-11-17 ES ES94900806T patent/ES2100664T3/es not_active Expired - Lifetime
- 1993-11-17 BR BR9307517A patent/BR9307517A/pt not_active Application Discontinuation
- 1993-11-17 DE DE69308883T patent/DE69308883T2/de not_active Expired - Fee Related
- 1993-11-17 WO PCT/EP1993/003170 patent/WO1994012489A1/en not_active Ceased

Also Published As

Publication number	Publication date
JPH08503476A (ja)	1996-04-16
DE69308883T2 (de)	1997-07-24
AU5562394A (en)	1994-06-22
EP0670834B1 (en)	1997-03-12
EP0670834A1 (en)	1995-09-13
JP2848706B2 (ja)	1999-01-20
ES2100664T3 (es)	1997-06-16
WO1994012489A1 (en)	1994-06-09
DE69308883D1 (de)	1997-04-17
BR9307517A (pt)	1999-08-24

Legal Events

Date	Code	Title	Description
2002-06-20	MK14	Patent ceased section 143(a) (annual fees not paid) or expired

Publication	Publication Date	Title
AU682835B2 (en)	1997-10-23	Alkylidene glycerol surfactants and detergent compositions containing them
CA2060698C (en)	1997-09-30	Detergent compositions
US5520839A (en)	1996-05-28	Laundry detergent composition containing synergistic combination of sophorose lipid and nonionic surfactant
USH1818H (en)	1999-11-02	Detergent and cleaning compositions derived from new detergent alcohols
US5417879A (en)	1995-05-23	Synergistic dual-surfactant detergent composition containing sophoroselipid
EP1558717A1 (en)	2005-08-03	Laundry detergent composition
CA2713280C (en)	2012-02-21	Laundry detergent comprising highly ethoxylated nonionic surfactant
US6720298B2 (en)	2004-04-13	Detergent compositions comprising an ethoxylated alcohol and alkyl ioenzene sulfonate
WO2003031548A1 (en)	2003-04-17	Detergent compositions
CA1040962A (en)	1978-10-24	Monionic detergent composition
EP0423968A1 (en)	1991-04-24	Detergent composition
US6608016B2 (en)	2003-08-19	Detergent compositions
EP1254202B1 (en)	2006-09-27	Detergent compositions
CA2236438A1 (en)	1997-05-09	Peroxyacids
JP2000508687A (ja)	2000-07-11	非イオン界面活性剤組成物