ES2386978T3 - Esterquats poliméricos con cadenas laterales asimétricas - Google Patents

Info

Publication number

ES2386978T3

ES2386978T3 ES07004301T ES07004301T ES2386978T3 ES 2386978 T3 ES2386978 T3 ES 2386978T3 ES 07004301 T ES07004301 T ES 07004301T ES 07004301 T ES07004301 T ES 07004301T ES 2386978 T3 ES2386978 T3 ES 2386978T3

Authority

ES

Spain

Prior art keywords

acid

acids

sorbitan

esters

mixtures

Prior art date

2007-03-02

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.)

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• 239000000203 mixture Substances 0.000 claims abstract description 72
• 150000002148 esters Chemical class 0.000 claims abstract description 35
• 150000001991 dicarboxylic acids Chemical class 0.000 claims abstract description 16
• 150000002763 monocarboxylic acids Chemical class 0.000 claims abstract description 13
• 229940100198 alkylating agent Drugs 0.000 claims abstract description 12
• 239000002168 alkylating agent Substances 0.000 claims abstract description 12
• -1 hydroxyethyl radical Chemical group 0.000 claims description 66
• 125000004432 carbon atom Chemical group C* 0.000 claims description 26
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 18
• 238000000034 method Methods 0.000 claims description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
• 239000002537 cosmetic Substances 0.000 claims description 14
• WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 11
• 235000011037 adipic acid Nutrition 0.000 claims description 10
• 150000005690 diesters Chemical class 0.000 claims description 10
• UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 10
• 210000004209 hair Anatomy 0.000 claims description 10
• IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 10
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 10
• 239000001361 adipic acid Substances 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 235000021355 Stearic acid Nutrition 0.000 claims description 8
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 8
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 8
• 239000008117 stearic acid Substances 0.000 claims description 8
• 238000005956 quaternization reaction Methods 0.000 claims description 7
• POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 6
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 5
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 5
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 5
• 235000021357 Behenic acid Nutrition 0.000 claims description 5
• 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 5
• 239000005642 Oleic acid Substances 0.000 claims description 5
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 5
• 235000021314 Palmitic acid Nutrition 0.000 claims description 5
• 229940116226 behenic acid Drugs 0.000 claims description 5
• 238000005886 esterification reaction Methods 0.000 claims description 5
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 5
• WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 5
• 229960002446 octanoic acid Drugs 0.000 claims description 5
• 235000021313 oleic acid Nutrition 0.000 claims description 5
• DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 4
• URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 4
• 150000001735 carboxylic acids Chemical class 0.000 claims description 4
• GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 4
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
• DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 4
• 230000032050 esterification Effects 0.000 claims description 4
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 239000005639 Lauric acid Substances 0.000 claims description 3
• 239000002453 shampoo Substances 0.000 claims description 3
• OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 2
• OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 2
• 150000001502 aryl halides Chemical class 0.000 claims description 2
• KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 2
• 229940073608 benzyl chloride Drugs 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 2
• 150000008050 dialkyl sulfates Chemical class 0.000 claims description 2
• 239000001257 hydrogen Substances 0.000 claims description 2
• 229910052739 hydrogen Inorganic materials 0.000 claims description 2
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
• 210000003405 ileum Anatomy 0.000 claims description 2
• TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 2
• 150000001350 alkyl halides Chemical class 0.000 claims 1
• 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 83
• 235000014113 dietary fatty acids Nutrition 0.000 description 47
• 239000000194 fatty acid Substances 0.000 description 47
• 229930195729 fatty acid Natural products 0.000 description 47
• 150000004665 fatty acids Chemical class 0.000 description 37
• 239000000047 product Substances 0.000 description 27
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 25
• 239000002253 acid Substances 0.000 description 24
• 239000001993 wax Substances 0.000 description 24
• 239000003921 oil Substances 0.000 description 18
• 235000019198 oils Nutrition 0.000 description 18
• 150000001875 compounds Chemical class 0.000 description 15
• 150000003839 salts Chemical class 0.000 description 15
• 239000004094 surface-active agent Substances 0.000 description 14
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• 239000003795 chemical substances by application Substances 0.000 description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• 125000000217 alkyl group Chemical group 0.000 description 11
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 11
• 239000000126 substance Substances 0.000 description 11
• 229920001577 copolymer Polymers 0.000 description 10
• SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 10
• 150000002191 fatty alcohols Chemical class 0.000 description 10
• 239000002304 perfume Substances 0.000 description 10
• 229920000223 polyglycerol Polymers 0.000 description 10
• 229920005862 polyol Polymers 0.000 description 10
• 229920001296 polysiloxane Polymers 0.000 description 10
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
• 235000011187 glycerol Nutrition 0.000 description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
• 150000007513 acids Chemical class 0.000 description 8
• 229930182470 glycoside Natural products 0.000 description 8
• 229920000642 polymer Polymers 0.000 description 8
• 150000003077 polyols Chemical class 0.000 description 8
• 102000008186 Collagen Human genes 0.000 description 7
• 108010035532 Collagen Proteins 0.000 description 7
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
• 150000001298 alcohols Chemical class 0.000 description 7
• 239000003054 catalyst Substances 0.000 description 7
• 229920001436 collagen Polymers 0.000 description 7
• 239000003995 emulsifying agent Substances 0.000 description 7
• BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 239000003755 preservative agent Substances 0.000 description 7
• ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 6
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
• 229920001661 Chitosan Polymers 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• 125000002091 cationic group Chemical group 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 238000009826 distribution Methods 0.000 description 6
• 239000000686 essence Substances 0.000 description 6
• 229910052938 sodium sulfate Inorganic materials 0.000 description 6
• 235000011152 sodium sulphate Nutrition 0.000 description 6
• LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 5
• XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 5
• 235000013162 Cocos nucifera Nutrition 0.000 description 5
• 244000060011 Cocos nucifera Species 0.000 description 5
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical class OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
• 239000004166 Lanolin Substances 0.000 description 5
• IBYNMHGLXCSFEW-UHFFFAOYSA-N OOO.OS(O)(=O)=O Chemical class OOO.OS(O)(=O)=O IBYNMHGLXCSFEW-UHFFFAOYSA-N 0.000 description 5
• 229910019142 PO4 Inorganic materials 0.000 description 5
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
• 125000002947 alkylene group Chemical group 0.000 description 5
• 239000004359 castor oil Substances 0.000 description 5
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• 125000005456 glyceride group Chemical group 0.000 description 5
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
• 150000002338 glycosides Chemical group 0.000 description 5
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
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