WO2012139818A1 - Structured aqueous surfactant systems - Google Patents
Structured aqueous surfactant systems Download PDFInfo
- Publication number
- WO2012139818A1 WO2012139818A1 PCT/EP2012/053612 EP2012053612W WO2012139818A1 WO 2012139818 A1 WO2012139818 A1 WO 2012139818A1 EP 2012053612 W EP2012053612 W EP 2012053612W WO 2012139818 A1 WO2012139818 A1 WO 2012139818A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- surfactant
- cellulose
- oxidation
- oxidised
- polyoxyethylene
- Prior art date
Links
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 62
- 229920002678 cellulose Polymers 0.000 claims abstract description 64
- 239000001913 cellulose Substances 0.000 claims abstract description 62
- -1 polyoxyethylene Polymers 0.000 claims abstract description 44
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 26
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims abstract description 18
- 150000003138 primary alcohols Chemical class 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 12
- 229920001222 biopolymer Polymers 0.000 claims abstract description 12
- 239000003792 electrolyte Substances 0.000 claims abstract description 12
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract description 9
- 125000006353 oxyethylene group Chemical group 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 230000004048 modification Effects 0.000 claims abstract description 5
- 238000012986 modification Methods 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000002191 fatty alcohols Chemical class 0.000 claims description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 2
- 235000010980 cellulose Nutrition 0.000 description 59
- 230000003647 oxidation Effects 0.000 description 36
- 238000007254 oxidation reaction Methods 0.000 description 36
- 239000000203 mixture Substances 0.000 description 31
- 239000000463 material Substances 0.000 description 20
- 235000014113 dietary fatty acids Nutrition 0.000 description 17
- 239000000194 fatty acid Substances 0.000 description 17
- 229930195729 fatty acid Natural products 0.000 description 17
- 239000003945 anionic surfactant Substances 0.000 description 16
- 150000004665 fatty acids Chemical class 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 9
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 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 8
- 150000002148 esters Chemical class 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical compound O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002280 amphoteric surfactant Substances 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 3
- QTDIEDOANJISNP-UHFFFAOYSA-N 2-dodecoxyethyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOCCOS(O)(=O)=O QTDIEDOANJISNP-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000001720 carbohydrates 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
- 150000005690 diesters Chemical class 0.000 description 3
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- 230000001404 mediated effect Effects 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- ASKIVFGGGGIGKH-UHFFFAOYSA-N 2,3-dihydroxypropyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(O)CO ASKIVFGGGGIGKH-UHFFFAOYSA-N 0.000 description 2
- UXBLSWOMIHTQPH-UHFFFAOYSA-N 4-acetamido-TEMPO Chemical compound CC(=O)NC1CC(C)(C)N([O])C(C)(C)C1 UXBLSWOMIHTQPH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- LAPRIVJANDLWOK-UHFFFAOYSA-N laureth-5 Polymers CCCCCCCCCCCCOCCOCCOCCOCCOCCO LAPRIVJANDLWOK-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 108700004121 sarkosyl Proteins 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000000527 sonication Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000002888 zwitterionic surfactant Substances 0.000 description 2
- IJPCXCDDMAUNSI-ULAWRXDQSA-N (4r,5s,6r,7r)-4,5,6,7,8-pentahydroxyoctan-3-one Chemical compound CCC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO IJPCXCDDMAUNSI-ULAWRXDQSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- JHDBMHFWQRTXLV-UHFFFAOYSA-N 1-dodecoxydodecane;2-sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC JHDBMHFWQRTXLV-UHFFFAOYSA-N 0.000 description 1
- WECGLUPZRHILCT-GSNKCQISSA-N 1-linoleoyl-sn-glycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@H](O)CO WECGLUPZRHILCT-GSNKCQISSA-N 0.000 description 1
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 1
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- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
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- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
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- DBFHTTOOJDMDTI-KCMGSBMCSA-N C(CCCCCCCCCCCCCCCCC)(=O)O.CC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C(CCCCCCCCCCCCCCCCC)(=O)O.C(CCCCCCCCCCCCCCCCC)(=O)O.CC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)O.CC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C(CCCCCCCCCCCCCCCCC)(=O)O.C(CCCCCCCCCCCCCCCCC)(=O)O.CC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO DBFHTTOOJDMDTI-KCMGSBMCSA-N 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 229940080421 coco glucoside Drugs 0.000 description 1
- 229940071160 cocoate Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Polymers OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- JDRSMPFHFNXQRB-IBEHDNSVSA-N decyl glucoside Chemical compound CCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JDRSMPFHFNXQRB-IBEHDNSVSA-N 0.000 description 1
- 229940073499 decyl glucoside Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- GLSRFBDXBWZNLH-UHFFFAOYSA-L disodium;2-chloroacetate;2-(4,5-dihydroimidazol-1-yl)ethanol;hydroxide Chemical compound [OH-].[Na+].[Na+].[O-]C(=O)CCl.OCCN1CCN=C1 GLSRFBDXBWZNLH-UHFFFAOYSA-L 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229940068517 fruit extracts Drugs 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 229940068939 glyceryl monolaurate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- HKPGZZNQPUBKGQ-KAVXHDQVSA-N hexadecanoic acid (4R,5S,6R,7R)-4,5,6,7,8-pentahydroxyoctan-3-one Chemical compound CCC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCCCCCCCCCC(O)=O HKPGZZNQPUBKGQ-KAVXHDQVSA-N 0.000 description 1
- UCZNZRYBJXGIAV-SSPAHAAFSA-N hexadecanoic acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.CCCCCCCCCCCCCCCC(O)=O UCZNZRYBJXGIAV-SSPAHAAFSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229940031726 laureth-10 Drugs 0.000 description 1
- 229940100556 laureth-23 Drugs 0.000 description 1
- 229940094506 lauryl betaine Drugs 0.000 description 1
- PYIDGJJWBIBVIA-UYTYNIKBSA-N lauryl glucoside Chemical compound CCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PYIDGJJWBIBVIA-UYTYNIKBSA-N 0.000 description 1
- 229940048848 lauryl glucoside Drugs 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940044591 methyl glucose dioleate Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- DVEKCXOJTLDBFE-UHFFFAOYSA-N n-dodecyl-n,n-dimethylglycinate Chemical compound CCCCCCCCCCCC[N+](C)(C)CC([O-])=O DVEKCXOJTLDBFE-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 125000001117 oleyl 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])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000010951 particle size reduction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229940099549 polyglycerin-3 Drugs 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002459 porosimetry Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940096501 sodium cocoamphoacetate Drugs 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 229940045885 sodium lauroyl sarcosinate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- NTYZDAJPNNBYED-UHFFFAOYSA-M sodium;2-(2-dodecanoyloxypropanoyloxy)propanoate Chemical compound [Na+].CCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O NTYZDAJPNNBYED-UHFFFAOYSA-M 0.000 description 1
- ADWNFGORSPBALY-UHFFFAOYSA-M sodium;2-[dodecyl(methyl)amino]acetate Chemical compound [Na+].CCCCCCCCCCCCN(C)CC([O-])=O ADWNFGORSPBALY-UHFFFAOYSA-M 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- BUFQZEHPOKLSTP-UHFFFAOYSA-M sodium;oxido hydrogen sulfate Chemical class [Na+].OS(=O)(=O)O[O-] BUFQZEHPOKLSTP-UHFFFAOYSA-M 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940032085 sucrose monolaurate Drugs 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/731—Cellulose; Quaternized cellulose derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
- C11D17/0026—Structured liquid compositions, e.g. liquid crystalline phases or network containing non-Newtonian phase
Definitions
- This invention relates to structured aqueous surfactant systems comprising modified cellulose and surfactant.
- Cellulose is a plentiful, and consequently inexpensive, biopolymer. However, in its unmodified form it is completely insoluble and cannot be dispersed into an aqueous liquid composition to achieve a stable, thickened, product.
- cellouronates or cellouronic acids which are more water dispersible than cellulose but still relatively insoluble.
- WO 2010/076292 describes how this type of oxidised cellulose may be used as an alternative structurant for aqueous detergent compositions. This enables the formulator to replace surfactant required for structuring with relatively low concentrations of low cost, partially oxidised, dispersed modified cellulose. These reduced surfactant compositions nonetheless maintain a thick gel-like consistency which allows suspension of solids or gases, such as bubbles, capsules or beads. According to WO2010/076292, in order to provide gelled material it is essential to use anionic or zwitterionic surfactants. The use of a nonionic surfactant (sorbitan trioleate) does not result in a gel.
- sorbitan trioleate sorbitan trioleate
- a structured aqueous surfactant system comprising: a) at least 0.1 wt% nonionic surfactant which is a polyoxyethylene nonionic surfactant having a hydrophilic head group with at least four oxyethylene units;
- a process to manufacture a structured aqueous surfactant system comprising the steps of:
- nonionic surfactant which is a polyoxyethylene nonionic surfactant having a hydrophilic head group with at least four oxyethylene units, and (iii) optionally also adding up to 10 wt% non-surfactant electrolyte consisting of low molecular weight salt,
- the cellulose starting material Several factors influence the choice of a suitable starting material.
- Characterisation of surface area or porosity is readily achieved by porosimetry or BET measurements. In general, those starting materials that oxidise more rapidly due to their low crystallinity and higher surface area and/or porosity, prove easier to disperse than those that oxidise less rapidly.
- the rate of oxidation is also affected by the dimensions of the particles of cellulose starting material; the reduction in rate for longer (>500 micron) fibres is significant. Fibres less than 500 microns long are therefore preferred for this reason and due to the added difficulty in agitation of the longer fibres. While oxidation results in significant gross particle size reduction, this does not compensate for decreased fibril surface accessibility in the long fibres.
- Celluloses that have not been previously subjected to acid hydrolysis are a preferred starting material, due to reactivity, cost and resultant product
- a-cellulose for example filter aid fibres
- the oxidation process also serves to bleach coloured components, such as lignin, in such unbleached cellulose starting materials. This then renders such materials more suitable for use in contexts where visual clarity of the end product is desirable, for example transparent personal care formulations.
- TEMPO-mediated oxidation of cellulose is preferred (i.e. 2,2,6,6-tetramethylpiperidine-1 -oxyl and related nitroxy radical species).
- the process proceeds well without cooling, at relatively high weight % cellulose in the initial suspension.
- Simple workup procedures afford clean material suitable for dispersion.
- Such TEMPO mediated oxidation of cellulose is described in the published literature and the skilled worker will be able as a matter of routine to adapt known methods to achieve the oxidation required by this invention.
- 2,2,6,6- tetramethylpiperidine-1 -oxyl (4-acetamido-TEMPO) as the radical transfer catalyst or mediator and sodium bromide co-catalyst for the oxidation. Elimination of chlorine from the oxidation system is environmentally desirable.
- 4-acetamido-TEMPO as radical transfer catalyst is also advantageous as, although it has a higher molecular weight than TEMPO, it has significantly lower vapour pressure reducing potential exposure hazards.
- Many other 4- substituted TEMPO analogues exist, but many, such as 4-hydroxy-TEMPO exhibit poor stability.
- TEMPO on solid supports or on soluble polymers may be used.
- Electrochemical oxidation is a potentially clean means of effecting oxidation of carbohydrate moieties, although mediation by a radical transfer catalyst (such as TEMPO) is still required.
- TEMPO radical transfer catalyst
- Laccase mediated oxidation which also requires a radical transfer catalyst (e.g. TEMPO) but replaces the oxidant with an enzyme, may advantageously be used.
- the term "degree of oxidation" of the modified cellulose means the percentage glucose units oxidised to carboxylic acid as measured by titration with sodium hydroxide. It is assumed that all oxidation takes place at the primary alcohol positions. A reasonable assumption, given that primary alcohol specific oxidation chemistry is employed. Furthermore it is assumed that all oxidation leads to carboxylic acid formation. Degree of polymerisation (DP) does not seem greatly to influence the
- the degree of oxidation of the modified cellulose lies in the range 10 to 70%. As the degree of oxidation increases, the amount of soluble material produced will rise and this reduces the yield of insoluble structuring material, thus the higher degrees of oxidation confer no real structuring benefits. For this reason, it is preferred to restrict the degree of oxidation to 60%, or even 50% and the most preferred modified materials have degrees of oxidation even lower than 40% or sometimes even lower than 30%.
- the modified cellulose To achieve a high enough dispersibility/solubility for the modified cellulose to act as a structurant it must be oxidised to at least 10%. The exact amount of oxidation required for a minimum effect will vary according to the starting material used. Preferably, it is at least 15% oxidised and most preferably, at least 20% oxidised. Dispersal of the modified cellulose
- Oxidised, dispersed cellulose is a largely insoluble polymer that occurs in the form of well dispersed fibrils rather than isolated solvated polymer chains.
- the fibrils have a large aspect ratio and are thin enough to provide almost transparent dispersions.
- Carboxylate groups provide anionic surface charge, which results in a degree of repulsion between fibrils, militating against their reassociation into larger structures.
- Addition of acid to dispersions of oxidised cellulose results in separation of gelled material while at pH between ca 5-9 fibrils may be maintained in a dispersed form as the COO- salt of an appropriate counterion.
- the amount of modified cellulose biopolymer in the surfactant system of the invention preferably ranges from 1 to 2 wt% (by total weight modified cellulose biopolymer based on the total weight of the emulsion).
- nonionic surfactant which is a polyoxyethylene nonionic surfactant having a hydrophilic head group with at least four oxyethylene units
- Preferred examples of such materials include polyoxyethylene ethers of fatty alcohols, acids and amides, having from 8 to 20 carbon atoms in the fatty chain and from 4 to about 100 oxyethylene units.
- Particularly preferred examples of such materials include the condensation products of aliphatic (Cs to ds) primary or secondary, saturated or unsaturated, linear or branched chain alcohols with ethylene oxide and having from 4 to 30 ethylene oxide groups. These include, for example, Cs to C15 primary or secondary alcohols or mixtures thereof, condensed with from 4 to 30 moles of ethylene oxide.
- Specific examples include
- nonionic surfactants for use in the invention include the condensates of from 4 to 80 moles of ethylene oxide with fatty acid partial esters of sorbitan, in which the fatty acid has from 8 to 20 carbon atoms in the fatty chain and may be saturated or unsaturated, linear or branched.
- Suitable nonionic surfactants include the condensates of from 4 to 80 moles of ethylene oxide with fatty acid partial esters of sorbitan, in which the fatty acid has from 8 to 20 carbon atoms in the fatty chain and may be saturated or unsaturated, linear or branched.
- a specific example is polyoxyethylene (20) sorbitan monolaurate.
- the amount of polyoxyethylene nonionic surfactant in the surfactant system of the invention generally ranges from about 0.2% to about 40%, and preferably ranges from about 1 to 15 wt%, more preferably from about 2 to 12 wt% (by total weight polyoxyethylene nonionic surfactant based on the total weight of the surfactant system).
- a preferred surfactant system comprises less than 0.2 wt% anionic surfactant (by total weight anionic surfactant based on the total weight of the surfactant system). More preferably such a surfactant system is substantially free of anionic surfactant.
- substantially free in this particular context generally means that the surfactant system comprises less than 0.1 %, more preferably less than 0.01 %, most preferably less than 0.001 % by total weight anionic surfactant based on the total weight of the surfactant system.
- co-surfactants examples include:
- nonionic co-surfactants examples include fatty acids and fatty acid esters, ethers, hemi-acetals or acetals of polyhydroxylic compounds or a fatty acid amide which is N-substituted with the residue of a polyhydroxylic compound.
- Suitable fatty acids include those of formula R 1 -COOH, where R 1 is a Cs to C24, preferably a C12 to 22 hydrocarbyl, preferably alkyl or alkenyl, group.
- R 1 is a Cs to C24, preferably a C12 to 22 hydrocarbyl, preferably alkyl or alkenyl, group.
- An example is coconut fatty acid.
- Suitable esters of polyhydroxylic compounds include saccharide esters, and particularly mono- and/or diesters of fatty acids (as defined above) with a sugar, especially sucrose, fructose, glucose and/or alkylglucose (e.g. methylglucose or ethylglucose).
- a sugar especially sucrose, fructose, glucose and/or alkylglucose (e.g. methylglucose or ethylglucose).
- Commercially available sugar esters are usually mixtures
- glucose palmitate methylglucose isostearate, methylglucose laurate, methylglucose sesquistearate (mixture of the mono- and diesters), alkylglucose palmitates such as methylglucose or ethylglucose palmitate, methyl glucose dioleate, methyl glucose sesquiisostearate, sucrose palmitate, sucrose stearate and sucrose monolaurate.
- polyglyceryl ethers of the above-described sugar esters such as polyglyceryl-3 methylglucose distearate (a diester of stearic acid and the condensation product of methylglucose and polyglycerin-3).
- esters of polyhydroxylic compounds include esters of fatty acids, particularly fatty acids having from 8 to 24, preferably 12 to 22, more preferably 16 to 20 carbon atoms, and polyols, particularly glycerol, or a polyglycerol, or an anhydrosaccharide such as sorbitan.
- Suitable ethers of polyhydroxylic compounds include alkyl polysaccharides of the formula: R 1 -0-(G) a , where R 1 is as defined above for fatty acids; each G is independently a saccharide residue, preferably a glucose residue and a is from 1 to about 5. Examples include decylglucoside, caprylyl/capryl glucoside, laurylglucoside, cocoglucoside, cetostearyl glucoside, arachidyl glucoside, and cocoylethylglucoside.
- nonionic co-surfactant includes fatty acid esters of hydroxycarboxylic acids, in which the fatty acid typically has from 8 to 24, preferably from 12 to 22, more preferably from 16 to 20 carbon atoms and the hydroxycarboxylic acid is preferably citric acid.
- N-substituted fatty acid amides in which the N-substituent is the residue of a polyhydroxylic compound, for example a saccharide residue such as a glucosyl group.
- This type of emulsifier typically has the formula: R 1 -CO-NR 5 R 6 , where R 1 is as defined above for fatty acids; R 5 is a hydrogen atom, a Ci to Ce alkyl group or a group of the formula R 6 ; and R 6 is a polyhydroxyl hydrocarbyl group, particularly a group containing from 3 to 10 carbon atoms and 2 to 6 hydroxyl groups, preferably a glucosyl residue.
- the amount of nonionic co-surfactant in the surfactant system of the invention generally ranges from 0 to 10 wt%, and when used, preferably ranges from 1 to 5 wt% (by total weight nonionic co-surfactant based on the total weight of the emulsion).
- anionic surfactants examples include sodium lauroyl sarcosinate, sodium lauroyl lactylate, sodium cocoyi glutamate, disodium polyglucose sulfosuccinate / citrate, sodium lauryl ether sulphate (1 -3 EO).
- Suitable anionic surfactants are the alkyl sulphates, alkyl ether sulphates, alkaryl sulphonates, alkanoyl isethionates, alkyl succinates, alkyl sulphosuccinates, alkyl ether sulphosuccinates, N-alkyl sarcosinates, alkyl phosphates, alkyl ether phosphates, and alkyl ether carboxylic acids and salts thereof, especially their sodium, magnesium, ammonium and mono-, di- and triethanolamine salts.
- the alkyl and acyl groups generally contain from 8 to 18, preferably from 10 to 16 carbon atoms and may be unsaturated.
- alkyl ether sulphates, alkyl ether sulphosuccinates, alkyl ether phosphates and alkyl ether carboxylic acids and salts thereof may contain from 1 to 20 ethylene oxide or propylene oxide units per molecule.
- anionic surfactants include sodium oleyl succinate, ammonium lauryl sulphosuccinate, sodium lauryl sulphate, sodium lauryl ether sulphate, sodium lauryl ether sulphosuccinate, ammonium lauryl sulphate, ammonium lauryl ether sulphate, sodium dodecylbenzene sulphonate, triethanolamine
- dodecylbenzene sulphonate sodium cocoyi isethionate, sodium lauryl isethionate, lauryl ether carboxylic acid and sodium N-lauryl sarcosinate. Mixtures of any of the foregoing anionic surfactants may also be used.
- alkyl amine oxides alkyl betaines, alkyl amidopropyl betaines, alkyl
- amphoteric surfactants include lauryl amine oxide, cocodimethyl sulphopropyl betaine, lauryl betaine, cocamidopropyl betaines, olivamidopropyl betaines and sodium cocoamphoacetate. Mixtures of any of the foregoing amphoteric surfactants may also be suitable.
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR112013026130A BR112013026130A2 (en) | 2011-04-12 | 2012-03-02 | structured aqueous surfactant system |
US14/009,273 US9144540B2 (en) | 2011-04-12 | 2012-03-02 | Structured aqueous surfactant systems |
EP12707094.4A EP2697350B1 (en) | 2011-04-12 | 2012-03-02 | Structured aqueous surfactant systems |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11162005 | 2011-04-12 | ||
EP11162005.0 | 2011-04-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2012139818A1 true WO2012139818A1 (en) | 2012-10-18 |
Family
ID=44544013
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PCT/EP2012/053612 WO2012139818A1 (en) | 2011-04-12 | 2012-03-02 | Structured aqueous surfactant systems |
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US (1) | US9144540B2 (en) |
EP (1) | EP2697350B1 (en) |
BR (1) | BR112013026130A2 (en) |
WO (1) | WO2012139818A1 (en) |
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DE102012215962A1 (en) * | 2012-09-10 | 2014-03-13 | Robert Bosch Gmbh | Control device and method for determining the rotor angle of a synchronous machine |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US5437810A (en) * | 1994-04-26 | 1995-08-01 | Colgate-Palmolive Co. | Aqueous liquid detergent compositions containing oxidized polysaccharides |
WO2010076292A1 (en) | 2008-12-29 | 2010-07-08 | Unilever Plc | Structured aqueous detergent compositions |
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US5653970A (en) | 1994-12-08 | 1997-08-05 | Lever Brothers Company, Division Of Conopco, Inc. | Personal product compositions comprising heteroatom containing alkyl aldonamide compounds |
ES2230901T3 (en) * | 1998-12-05 | 2005-05-01 | Imperial Chemical Industries Plc | EMULSIONING SYSTEM AND EMULSIONS. |
FR2794466B1 (en) * | 1999-06-02 | 2001-06-29 | Oreal | COMPOSITION IN THE FORM OF AN OIL-IN-WATER EMULSION CONTAINING CELLULOSE FIBRILLES AND ITS IN PARTICULAR COSMETIC USES |
AR027842A1 (en) * | 1999-08-23 | 2003-04-16 | Kimberly Clark Co | AN ABSORBENT ARTICLE WHICH MAINTAINS OR IMPROVES SKIN HEALTH |
DE10059430A1 (en) | 2000-11-30 | 2002-06-06 | Cognis Deutschland Gmbh | Finely divided emulsions |
JP2009209217A (en) | 2008-02-29 | 2009-09-17 | Univ Of Tokyo | Method for modifying cellulose, modified cellulose, cello-uronic acid and cellulose crystallite |
US10716748B2 (en) * | 2010-04-30 | 2020-07-21 | Momentive Performance Materials Inc. | Method of treating hair |
-
2012
- 2012-03-02 EP EP12707094.4A patent/EP2697350B1/en not_active Not-in-force
- 2012-03-02 BR BR112013026130A patent/BR112013026130A2/en not_active IP Right Cessation
- 2012-03-02 WO PCT/EP2012/053612 patent/WO2012139818A1/en active Application Filing
- 2012-03-02 US US14/009,273 patent/US9144540B2/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5437810A (en) * | 1994-04-26 | 1995-08-01 | Colgate-Palmolive Co. | Aqueous liquid detergent compositions containing oxidized polysaccharides |
WO2010076292A1 (en) | 2008-12-29 | 2010-07-08 | Unilever Plc | Structured aqueous detergent compositions |
Non-Patent Citations (1)
Title |
---|
HOFFMANN H ET AL: "Surfactant gels", CURRENT OPINION IN COLLOID AND INTERFACE SCIENCE, LONDON, GB, vol. 1, no. 6, 1 December 1996 (1996-12-01), pages 726 - 739, XP027090810, ISSN: 1359-0294, [retrieved on 19961201] * |
Also Published As
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US20140142202A1 (en) | 2014-05-22 |
US9144540B2 (en) | 2015-09-29 |
EP2697350B1 (en) | 2015-09-02 |
BR112013026130A2 (en) | 2016-12-27 |
EP2697350A1 (en) | 2014-02-19 |
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