EP0670834B1 - Alkylidene glycerol surfactants and detergent compositions containing them - Google Patents
Alkylidene glycerol surfactants and detergent compositions containing them Download PDFInfo
- Publication number
- EP0670834B1 EP0670834B1 EP94900806A EP94900806A EP0670834B1 EP 0670834 B1 EP0670834 B1 EP 0670834B1 EP 94900806 A EP94900806 A EP 94900806A EP 94900806 A EP94900806 A EP 94900806A EP 0670834 B1 EP0670834 B1 EP 0670834B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- detergent composition
- compound
- cosurfactant
- diglycerol
- surfactant
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 239000003599 detergent Substances 0.000 title claims abstract description 40
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 34
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims description 44
- -1 Alkylidene glycerol Chemical compound 0.000 title abstract description 78
- 239000007788 liquid Substances 0.000 claims abstract description 24
- 239000004064 cosurfactant Substances 0.000 claims abstract description 15
- 239000000080 wetting agent Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000002736 nonionic surfactant Substances 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical group OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 8
- 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
- 150000001299 aldehydes Chemical class 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
- 239000003945 anionic surfactant Substances 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
- 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
- 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
- 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
- 239000000463 material Substances 0.000 abstract description 14
- 125000001118 alkylidene group Chemical group 0.000 abstract description 9
- 239000002689 soil Substances 0.000 abstract description 9
- 230000002195 synergetic effect Effects 0.000 abstract description 5
- 239000007844 bleaching agent Substances 0.000 description 19
- 235000011187 glycerol Nutrition 0.000 description 18
- 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
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 239000010457 zeolite Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 229910021536 Zeolite Inorganic materials 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
- 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 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 5
- 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
- 238000000526 short-path distillation Methods 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
- 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
- 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
- 150000001298 alcohols Chemical class 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
- 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 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
- 239000012190 activator Substances 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
- 125000000129 anionic group Chemical group 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
- 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
- 238000009472 formulation Methods 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
- 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
- 159000000000 sodium salts Chemical class 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
- 239000002253 acid Substances 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
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
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- 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
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- 239000008233 hard water Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
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- 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
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- 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
- 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
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 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
Definitions
- the present invention provides novel alkylidene glycerol surfactants useful in detergent compositions.
- Condensation products of aldehydes with glycerol are described in GB 414 772 (Johnson).
- lauric aldehyde may be reacted with glycerol to give the monoglycerol acetal, described as having a five-membered dioxolane ring structure:
- Such products are hydrophobic but introduction of water-solubilising groups gives products which are useful as wetting, washing, foaming and dispersing agents.
- the compound shown above does not itself exhibit foaming properties, but may be converted by reaction with chlorosulphonic acid to give a high-foaming anionic surfactant, or ethoxylated to give a nonionic surfactant.
- EP 12 543A discloses cyclic acetals and ketals of glycerol and other polyols, and their use as emollients in cosmetic, toilet and household cleaning compositions.
- reaction product of an aldehyde RCHO with glycerol which comprises a mixture of a five-membered ring structure A (1,3-dioxolane) and a six-membered ring structure B (1, 3-dioxane), the proportions of which can be varied in a known manner by varying the reaction conditions:
- These materials may optionally be alkoxylated, acylated or alkylated.
- Monoglycerol ketals are disclosed in US 3 909 460 and US 3 948 953 (McCoy/Texaco Inc). These materials, prepared by the condensation of ketones with glycerol, have the formula where R and R' are alkyl groups containing in total 6 to 30 carbon atoms. Unlike the monoglycerol acetals, these materials can exist only in a five-membered ring form. Like the monoglycerol acetals, these materials require the introduction of a solubilising group, for example, sulphate or polyoxyethylene, to give water-soluble surfactants.
- a solubilising group for example, sulphate or polyoxyethylene
- the present inventors have now prepared acetals and ketals containing two or more glycerol residues. These materials, which are liquids or soft solids, behave as effective, water-soluble nonionic surfactants especially useful in detergent compositions for washing fabrics. Certain combinations with other, known surfactants have been found to display synergistic oily soil detergency.
- the new materials behave comparably to ethoxylated alcohol nonionic surfactants, and are potential candidates for replacing them wholly or partially in detergent compositions if a reduction in the use of ethoxylated materials should become considered desirable on environmental grounds.
- the present invention accordingly provides a compound of the formula I: wherein R 1 represents a linear or branched alkyl or alkenyl group and R 2 represents a hydrogen atom or a linear or branched alkyl or alkenyl group, the total number of carbon atoms in R 1 and R 2 being from 7 to 17; and A represents a monoglycerol or diglycerol unit.
- a second subject of the present invention is the use of a compound as defined in the previous paragraph as a surfactant or wetting agent.
- a third subject of the present invention is a detergent composition having a surfactant system comprising a compound as defined above.
- a fourth subject of the present invention is a process for the preparation of a compound of the formula I, in which an aldehyde or ketone of the formula R 1 -CO-R 2 is reacted with an oligomer of glycerol.
- the compounds of the formula I given above are believed to be novel materials.
- the novelty resides in the presence of more than one - specifically two or three - glycerol units in the molecule.
- These two classes of compounds will be referred to respectively as alkylidene diglycerols and alkylidene triglycerols.
- the diglycerols (A is a monoglycerol unit) exist as a mixture of two structural isomers, of the formulae IIa and IIb: the linear isomer IIa being the predominant species.
- the triglycerols (A is a diglycerol unit) exist as a mixture of six structural isomers, as shown in the following formulae IIIa to IIIf. Again, the linear isomer IIIa predominates.
- the predominant linear isomers IIa and IIIa of the alkylidene di- and triglycerols may be represented by the general formula Ia: wherein n is 1 or 2.
- the total number of carbon atoms in the groups R 1 and R 2 in the compounds of the invention may range from 7 to 17, preferably from 9 to 13. In principle the carbon atoms may be distributed in any proportions between the two groups.
- the compounds studied by the present inventors fall into two classes: those in which R 2 is a hydrogen atom, and those in which R 2 is a methyl group.
- R 1 in both cases is a linear or branched alkyl or alkenyl group.
- R 2 is a hydrogen atom, derived from an aldehyde R 1 CHO
- 1-alkylidene (di- or tri-)glycerols or (di- or tri-)glycerol acetals while compounds in which R 2 is a methyl group, derived from a methyl ketone R 1 COCH 3 , are referred to as 2-alkylidene (di- or tri-)glycerols or (di- or tri-)glycerol ketals.
- R 2 is a hydrogen atom (1-alkylidene di- and triglycerols, or di- or triglycerol acetals) also exist in a six-membered ring isomeric form Ib:
- HLB hydrophilic-lipophilic balance
- alkylidene glycerols range from liquids to solids depending on the length and nature of the alkyl or alkenyl chain, the number of glycerol units in the molecule, and the particular isomer or mixture or isomers present.
- the linear 1- and 2-decylidene diglycerols are liquids of low viscosity, and are thus especially suitable for formulation into liquid detergent compositions, more especially non-aqueous liquid detergent compositions.
- the dodecylidene diglycerols are solids, and preferred for incorporation into particulate detergent compositions.
- the HLB values of the diglycerols are estimated from phase behaviour to be 9.5-10.5, comparable to C 12 ethoxylated alcohol having an average degree of ethoxylation of 3-4 (hereinafter referred to for convenience as C 12 EO 3-4 ). However, their oily soil detergency is somewhat better.
- These materials may advantageously be used in combination with cosurfactants of higher HLB (preferably >9, more preferably 9-13), such as sulphate and sulphonate-type anionic surfactants and more highly ethoxylated nonionic surfactants, for example, C 8-18 EO 5-10 .
- cosurfactants of higher HLB preferably >9, more preferably 9-13
- sulphate and sulphonate-type anionic surfactants and more highly ethoxylated nonionic surfactants, for example, C 8-18 EO 5-10 .
- the linear decylidene and dodecylidene triglycerols are soft liquid-crystalline solids, suitable for incorporation into both aqueous liquid and particulate detergent compositions. They are estimated to have HLB values in the range 12-13, comparable to C 12 EO 8 nonionic surfactant.
- the oily soil detergency is very similar. These materials may most suitably be used in combination with cosurfactants of lower HLB (preferably ⁇ 9, more preferably 7-9), for example, C 8-18 EO 2-6 . Synergistic oily soil detergency has been observed with C 12 EO 3 .
- novel alkylidene di- and triglycerols of the invention may be prepared by condensation of the appropriate aldehyde or ketone with a glycerol oligomer or mixture of oligomers.
- novel surfactants of the present invention may be incorporated in detergent compositions of all physical types, for example, powders, liquids, gels and solid bars.
- compositions whatever their physical form, will generally contain detergent-active compounds and detergency builders, and may optionally contain bleaching components and other active ingredients to enhance performance and properties.
- the detergent compositions of the invention will contain a surfactant system comprising one or more detergent-active compounds (surfactants), the surfactant system consisting at least in part of an alkylidene di- or triglycerol in accordance with the present invention.
- surfactants one or more detergent-active compounds (surfactants)
- the surfactant system consisting at least in part of an alkylidene di- or triglycerol in accordance with the present invention.
- one or more cosurfactants may also be present. These may be chosen from soap and non-soap anionic, cationic, nonionic, amphoteric and zwitterionic detergent-active compounds, and mixtures thereof. Many suitable detergent-active compounds are available and are fully described in the literature, for example, in "Surface-Active Agents and Detergents", Volumes I and II, by Schwartz, Perry and Berch.
- the preferred detergent-active compounds that can be used are soaps and synthetic non-soap anionic and nonionic compounds.
- Anionic surfactants are well-known to those skilled in the art. Examples include alkylbenzene sulphonates, particularly linear alkylbenzene sulphonates having an alkyl chain length of C 8 -C 15 ; primary and secondary alkyl sulphates, particularly C 12 -C 15 primary alkyl sulphates; alkyl ether sulphates; olefin sulphonates; alkyl xylene sulphonates; dialkyl sulphosuccinates; and fatty acid ester sulphonates.
- Sodium salts are generally preferred.
- Nonionic surfactants that may be used include the primary and secondary alcohol ethoxylates, especially the C 8- C 20 aliphatic alcohols ethoxylated with an average of from 1 to 20 moles of ethylene oxide per mole of alcohol, and more especially the C 10- C 15 primary and secondary aliphatic alcohols ethoxylated with an average of from 1 to 10 moles of ethylene oxide per mole of alcohol.
- Non-ethoxylated nonionic surfactants include alkylpolyglycosides, glycerol monoethers, and polyhydroxyamides (glucamide).
- the total amount of surfactant present will depend on the intended end use and may be as low as 0.5 wt%, for example, in a machine dishwashing composition, or as high as 60 wt%, for example, in a composition for washing fabrics by hand. In compositions for machine washing of fabrics, an amount of from 5 to 40 wt% is generally appropriate.
- the detergent compositions of the invention will generally also contain one or detergency builders.
- the total amount of detergency builder in the compositions will suitably range from 5 to 80 wt%, preferably from 10 to 60 wt% in powders, from 5 to 25 wt% in aqueous liquids and from 10 to 40 wt% in non-aqueous liquids.
- Inorganic builders that may be present include sodium carbonate, if desired in combination with a crystallisation seed for calcium carbonate, as disclosed in GB 1 437 950 (Unilever); crystalline and amorphous aluminosilicates, for example, zeolites as disclosed in GB 1 473 201 (Henkel), amorphous aluminosilicates as disclosed in GB 1 473 202 (Henkel) and mixed crystalline/amorphous aluminosilicates as disclosed in GB 1 470 250 (Procter & Gamble); and layered silicates as disclosed in EP 164 514B (Hoechst).
- Inorganic phosphate builders for example, sodium orthophosphate, pyrophosphate and tripolyphosphate, may also be present, but on environmental grounds those are no longer preferred.
- Zeolite builders may suitably be present in amounts of from 5 to 60 wt%, preferably from 10 to 50 wt%. Amounts of from 10 to 45 wt% are being especially suitable for particulate (machine) fabric washing compositions.
- the zeolite used in most commercial particulate detergent compositions is zeolite A.
- maximum aluminium zeolite P zeolite MAP
- Zeolite MAP is an alkali metal aluminosilicate of the P type having a silicon to aluminium ratio not exceeding 1.33, preferably not exceeding 1.15, and more preferably not exceeding 1.07.
- Organic builders that may be present include polycarboxylate polymers such as polyacrylates, acrylic/maleic copolymers, and acrylic phosphinates; monomeric polycarboxylates such as citrates, gluconates, oxydisuccinates, glycerol mono-, di- and trisuccinates, carboxymethyloxysuccinates, carboxymethyloxymalonates, dipicolinates, hydroxyethyliminodiacetates, alkyl- and alkenylmalonates and succinates; and sulphonated fatty acid salts. This list is not intended to be exhaustive.
- polycarboxylate polymers such as polyacrylates, acrylic/maleic copolymers, and acrylic phosphinates
- monomeric polycarboxylates such as citrates, gluconates, oxydisuccinates, glycerol mono-, di- and trisuccinates, carboxymethyloxysuccinates, carboxymethyloxymalonates, dipicolinates,
- Especially preferred organic builders are citrates, suitably used in amounts of from 5 to 30 wt%, preferably from 10 to 25 wt%; and acrylic polymers, more especially acrylic/maleic copolymers, suitably used in amounts of from 0.5 to 15 wt%, preferably from 1 to 10 wt%.
- Builders both inorganic and organic, are preferably present in alkali metal salt, especially sodium salt, form.
- Detergent compositions according to the invention may also suitably contain a bleach system.
- Machine dishwashing compositions may suitably contain a chlorine bleach system, while fabric washing compositions may more desirably contain peroxy bleach compounds, for example, inorganic persalts or organic peroxyacids, capable of yielding hydrogen peroxide in aqueous solution.
- peroxy bleach compounds for example, inorganic persalts or organic peroxyacids, capable of yielding hydrogen peroxide in aqueous solution.
- Suitable peroxy bleach compounds include organic peroxides such as urea peroxide, and inorganic persalts such as the alkali metal perborates, percarbonates, perphosphates, persilicates and persulphates.
- organic peroxides such as urea peroxide
- inorganic persalts such as the alkali metal perborates, percarbonates, perphosphates, persilicates and persulphates.
- Preferred inorganic persalts are sodium perborate monohydrate and tetrahydrate, and sodium percarbonate.
- sodium percarbonate having a protective coating against destabilisation by moisture Especially preferred is sodium percarbonate having a protective coating against destabilisation by moisture.
- Sodium percarbonate having a protective coating comprising sodium metaborate and sodium silicate is disclosed in GB 2 123 044B (Kao).
- the peroxy bleach compound is suitably present in an amount of from 5 to 35 wt%, preferably from 10 to 25 wt%.
- the peroxy bleach compound may be used in conjunction with a bleach activator (bleach precursor) to improve bleaching action at low wash temperatures.
- the bleach precursor is suitably present in an amount of from 1 to 8 wt%, preferably from 2 to 5 wt%.
- Preferred bleach precursors are peroxycarboxylic acid precursors, more especially peracetic acid precursors and peroxybenzoic acid precursors; and peroxycarbonic acid precursors.
- An especially preferred bleach precursor suitable for use in the present invention is N,N,N',N'-tetracetyl ethylenediamine (TAED).
- a bleach stabiliser may also be present.
- Suitable bleach stabilisers include ethylenediamine tetraacetate (EDTA) and the polyphosphonates such as Dequest (Trade Mark), EDTMP.
- An especially preferred bleach system comprises a peroxy bleach compound (preferably sodium percarbonate or sodium perborate monohydrate) optionally together with a bleach activator), and a transition metal bleach catalyst as described and claimed in EP 458 397A, EP 458 398A and EP 509 787A (Unilever).
- a peroxy bleach compound preferably sodium percarbonate or sodium perborate monohydrate
- a bleach activator preferably sodium percarbonate or sodium perborate monohydrate
- a transition metal bleach catalyst as described and claimed in EP 458 397A, EP 458 398A and EP 509 787A (Unilever).
- Detergent compositions of the invention may contain alkali metal, preferably sodium, carbonate, in order to increase detergency and ease processing.
- Sodium carbonate may suitably be present in amounts ranging from 1 to 60 wt%, preferably from 2 to 40 wt%.
- compositions containing little or no sodium carbonate are also within the scope of the invention.
- powder flow may be improved by the incorporation of a small amount of a powder structurant, for example, a fatty acid (or fatty acid soap), a sugar, an acrylate or acrylate/maleate polymer, or sodium silicate.
- a powder structurant for example, a fatty acid (or fatty acid soap), a sugar, an acrylate or acrylate/maleate polymer, or sodium silicate.
- a preferred powder structurant is fatty acid soap, suitably present in an amount of from 1 to 5 wt%.
- detergent compositions of the invention include sodium silicate; antiredeposition agents such as cellulosic polymers; fluorescers; inorganic salts such as sodium sulphate; lather control agents or lather boosters as appropriate; proteolytic and lipolytic enzymes; dyes; coloured speckles; perfumes; foam controllers; and fabric softening compounds. This list is not intended to be exhaustive.
- alkylidene di- and triglycerols in accordance with the present invention may advantageously be incorporated into both aqueous and non-aqueous liquid detergent compositions.
- Aqueous liquids in accordance with the invention may be isotropic. Alternatively they may be structured liquids comprising a dispersion of lamellar droplets in an aqueous continuous phase, optionally containing suspended particulate solid. Structured liquids of this type without suspended solid are disclosed, for example, in US 4 244 840, while structured liquids containing suspended solids are disclosed in US 4 244 840 and also in EP 38 101A, EP 160 342A and EP 140 452A.
- the liquids may contain a deflocculating polymer as described and claimed in EP 346 995A (Unilever), suitably in an amount of from 0.01 to 5 wt%.
- Non-aqueous liquids in accordance with the invention contain not more than 5 wt%, and preferably less than 3 wt%, water. They may take the form of a particulate solid phase dispersed in a non-aqueous liquid phase, the latter comprising one or more nonionic surfactants, suitably in an amount of from 1 to 90 wt%, preferably from 5 to 75 wt% and more preferably from 20 to 60 wt%.
- the non-aqueous liquids may contain a hydrophobically modified dispersant, for example, a hydrophobic silica, to improve physical stability.
- a deflocculant for example, an acid as described and claimed in EP 266 199A (Unilever), may also advantageously be present.
- 1,1-Dimethoxydecane (22.0g, 0.10mol), diglycerol (86.0g, 0.52mol) and p-toluene sulphonic acid (0.25g) in dimethyl formamide (100 cm 3 ) were heated at 100°C for 7 hours.
- the reaction mixture was allowed to cool and water (400 cm 3 ) was added and the mixture extracted with ether (2x300 cm 3 ).
- the combined ether extracts were washed with water (2x250 cm 3 ) and brine (250 cm 3 ) and dried over anhydrous sodium sulphate.
- the solvent was removed at reduced pressure to give the crude product.
- Short path distillation using a Kugelrohr apparatus afforded pure 1-decylidene diglycerol (14.7g, 48%) .
- the compound was characterised by nuclear magnetic resonance (NMR) spectroscopy: delta H (360 MHz, CDCl 3 , TMS) 0.89 (3H, t, CH 3 -), 1.3-1.4 (14H, m, -(CH 2 ) 7 -), 1.65 (2H, m, C 8 H 17 -CH 2 -), 3.5-4.4 (10H, m, -O-CH 2 -CH(O)-CH 2 -O-), 4.88,4.98 (1H, t, C 9 H 19 -CH-).
- NMR nuclear magnetic resonance
- 1,1-Dimethoxydodecane (11.5g, 0.05mol), triglycerol (240g, 1.0mol) and p-toluene sulphonic acid (0.5g) in dimethyl formamide (250 cm 3 ) was heated at 100°C for 5 hours.
- the reaction mixture was allowed to cool and water (400 cm 3 ) was added and the mixture extracted with ether (2x300 cm 3 ).
- the combined ether extracts were washed with water (2x250 cm 3 ) and brine (250 cm 3 ) and dried over anhydrous sodium sulphate.
- the solvent was removed at reduced pressure to give the crude product.
- Short path distillation using a Kugelrohr apparatus was used to remove low boiling impurities to leave near-pure 1-dodecylidene triglycerol ( 14.2g, 70%).
- the compound was characterised by nuclear magnetic resonance (NMR) spectroscopy: delta H (360 MHz, CDCl 3 , TMS) 0.88 (3H, t, CH3-), 1.3-1.4 (18H, m, -(CH 2 ) 9 -), 1.64 (2H, m, C 10 H 21 -CH 2 -), 3.5-4.4 (15H, m, -O-CH 2 -CH(O)-CH 2 -O-), 4.88,4.97 (1H, t, C 11 H 23 -CH-).
- NMR nuclear magnetic resonance
- 3 H-radiolabelled triolein was used to assess soil removal. Knitted polyester test cloths carrying this soil (level about 1.9%) were washed in the Tergotometer UR 7227 for 20 minutes, the agitation being 70 rpm, the wash liquor volume being 500 ml, and the wash temperature being 40°C. The surfactants were used at a concentration of 1 g/litre in distilled water in the presence of sodium metaborate buffer (0.05M). Subsequent to the wash, 4 x 1 ml samples of wash liquor were removed from each tergotometer pot and the activity determined using a liquid scintillation counter.
- decylidene and dodecylidene diglycerols all showed synergistic detergency behaviour when used in combination with the high-HLB cosurfactants, primary alcohol sulphate (cocoPAS) and C 12 EO 8 ethoxylated alcohol.
- Triolein removal (%) 2-decylidene diglycerol cocoPAS 100 0 30 80 20 68 60 40 52 40 60 48 20 80 46 0 100 44
- Triolein removal (%) 2-dodecylidene diglycerol cocoPAS 100 0 8 80 20 60 60 40 68 40 60 66 20 80 58 0 100 44
- detergencies were measured by a method similar to that used in Examples 5 to 8, but the tergotometer wash liquors contained the following ingredients in 24° (French) hard water: g/litre surfactant (total) 1.00 zeolite 2.42 sodium carbonate 1.82 acrylic/maleic copolymer 0.592
- Triolein removal (%) 1-decylidene diglycerol cocoPAS 100 0 2.5 80 20 58.6 60 40 58.2 40 60 52.8 20 80 44.7 0 100 40.1
- Triolein removal (%) 1-dodecylidene diglycerol C 10-12 EO 7 nonionic 100 0 1.5 80 20 4.9 60 40 62.0 40 60 65.9 20 80 65.0 0 100 60.7
- Detergent powders incorporating the compounds of the invention may be prepared to the following formulations (weight %): 13 14 Decylidene or dodecylidene diglycerol 17 - Decylidene or dodecylidene triglycerol - 8.5 C 12-15 EO(av) 7 ethoxylate 8.5 zeolite 32 32 sodium carbonate 12 12 alkaline sodium silicate 0.5 0.5 fatty acid soap 2 2 sodium carboxymethylcellulose 0.6 0.6 sodium perborate monohydrate 15 15 TAED 6.5 6.5 bleach stabiliser (EDTMP) 0.4 0.4 silicone suds suppressor 0.4 0.4 enzymes 1.0 1.0 fluorescer 0.2 0.2 perfume 0.6 0.6 moisture and salts to 100%
- Example 15 non-aqueous liquid detergent
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
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Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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US981737 | 1992-11-25 | ||
US07/981,737 US5389279A (en) | 1991-12-31 | 1992-11-25 | Compositions comprising nonionic glycolipid surfactants |
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 |
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EP0670834A1 EP0670834A1 (en) | 1995-09-13 |
EP0670834B1 true EP0670834B1 (en) | 1997-03-12 |
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EP94900806A Expired - Lifetime EP0670834B1 (en) | 1992-11-25 | 1993-11-17 | Alkylidene glycerol surfactants and detergent compositions containing them |
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EP (1) | EP0670834B1 (pt) |
JP (1) | JP2848706B2 (pt) |
AU (1) | AU682835B2 (pt) |
BR (1) | BR9307517A (pt) |
DE (1) | DE69308883T2 (pt) |
ES (1) | ES2100664T3 (pt) |
WO (1) | WO1994012489A1 (pt) |
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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 |
IN263389B (pt) | 2005-11-22 | 2014-01-31 | Segetis Inc | |
BRPI0818370A2 (pt) | 2007-10-09 | 2017-05-16 | Segetis Inc | métodos de fabricar cetais e acetais |
CA2736636A1 (en) | 2008-09-25 | 2010-04-01 | Segetis, Inc. | Ketal ester derivatives |
JP5882204B2 (ja) | 2009-06-22 | 2016-03-09 | サジティス・インコーポレイテッド | ケタール化合物およびそれらの使用 |
US20110300083A1 (en) | 2010-05-10 | 2011-12-08 | Segetis, Inc. | Personal care formulations containing alkyl ketal esters and methods of manufacture |
JP5886856B2 (ja) | 2010-08-03 | 2016-03-16 | サジティス・インコーポレイテッド | アセタールおよびケタールの製造方法、ならびにこの方法により製造されるアセタールおよびケタール |
CA2803389C (en) | 2010-08-12 | 2016-10-11 | 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 |
WO2012033813A2 (en) | 2010-09-07 | 2012-03-15 | Segetis, Inc. | Compositions for dyeing keratin fibers |
US8188030B2 (en) | 2010-09-13 | 2012-05-29 | Segetis, Inc. | Fabric softener compositions and methods of manufacture thereof |
KR20130131323A (ko) | 2010-10-18 | 2013-12-03 | 세게티스, 인코포레이티드. | 카복시 에스터 케탈을 포함하는 수희석성 코팅 조성물, 그리고 그의 제조방법 및 용도 |
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 |
WO2014085609A1 (en) | 2012-11-29 | 2014-06-05 | Segetis, Inc. | Carboxy ester ketals, methods of manufacture, and uses thereof |
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)
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---|---|---|---|---|
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 |
ES2067255T3 (es) * | 1990-11-14 | 1995-03-16 | Oreal | Compuestos anfifilos no ionicos derivados del glicerol, su procedimiento de preparacion, compuestos intermedios correspondientes y composiciones que contienen dichos compuestos. |
-
1993
- 1993-11-17 JP JP6512694A patent/JP2848706B2/ja not_active Expired - Lifetime
- 1993-11-17 BR BR9307517A patent/BR9307517A/pt not_active Application Discontinuation
- 1993-11-17 WO PCT/EP1993/003170 patent/WO1994012489A1/en active IP Right Grant
- 1993-11-17 ES ES94900806T patent/ES2100664T3/es not_active Expired - Lifetime
- 1993-11-17 EP EP94900806A patent/EP0670834B1/en not_active Expired - Lifetime
- 1993-11-17 DE DE69308883T patent/DE69308883T2/de not_active Expired - Fee Related
- 1993-11-17 AU AU55623/94A patent/AU682835B2/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
BR9307517A (pt) | 1999-08-24 |
JP2848706B2 (ja) | 1999-01-20 |
EP0670834A1 (en) | 1995-09-13 |
WO1994012489A1 (en) | 1994-06-09 |
ES2100664T3 (es) | 1997-06-16 |
AU5562394A (en) | 1994-06-22 |
JPH08503476A (ja) | 1996-04-16 |
DE69308883T2 (de) | 1997-07-24 |
AU682835B2 (en) | 1997-10-23 |
DE69308883D1 (de) | 1997-04-17 |
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