MXPA00012657A - Liquid thickener for surfactant systems - Google Patents
Liquid thickener for surfactant systemsInfo
- Publication number
- MXPA00012657A MXPA00012657A MXPA/A/2000/012657A MXPA00012657A MXPA00012657A MX PA00012657 A MXPA00012657 A MX PA00012657A MX PA00012657 A MXPA00012657 A MX PA00012657A MX PA00012657 A MXPA00012657 A MX PA00012657A
- Authority
- MX
- Mexico
- Prior art keywords
- glucose
- lipophilic
- alkoxylated
- moles
- per mole
- Prior art date
Links
- 239000007788 liquid Substances 0.000 title claims abstract description 49
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 31
- 239000002562 thickening agent Substances 0.000 title abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 75
- 229920005862 polyol Polymers 0.000 claims abstract description 60
- -1 polyol compounds Chemical class 0.000 claims abstract description 48
- 150000003077 polyols Chemical class 0.000 claims abstract description 48
- 125000001424 substituent group Chemical group 0.000 claims abstract description 47
- 150000002303 glucose derivatives Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 27
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 23
- 239000008103 glucose Substances 0.000 claims description 23
- WQZGKKKJIJFFOK-VFUOTHLCSA-N β-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 23
- 239000003153 chemical reaction reagent Substances 0.000 claims description 20
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 20
- 239000000194 fatty acid Substances 0.000 claims description 20
- 150000004665 fatty acids Chemical class 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229920005628 alkoxylated polyol Polymers 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 7
- HOVAGTYPODGVJG-WLDMJGECSA-N Methylglucoside Chemical compound COC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HOVAGTYPODGVJG-WLDMJGECSA-N 0.000 claims description 6
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N Diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 3
- 150000002118 epoxides Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- WYUFTYLVLQZQNH-JAJWTYFOSA-N (2R,3R,4S,5S,6R)-2-ethoxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound CCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O WYUFTYLVLQZQNH-JAJWTYFOSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 150000002194 fatty esters Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 230000001264 neutralization Effects 0.000 claims description 2
- 229920000223 polyglycerol Polymers 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims 1
- 239000002453 shampoo Substances 0.000 abstract description 6
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000004615 ingredient Substances 0.000 description 10
- WSDISUOETYTPRL-UHFFFAOYSA-N DMDM hydantoin Chemical compound CC1(C)N(CO)C(=O)N(CO)C1=O WSDISUOETYTPRL-UHFFFAOYSA-N 0.000 description 9
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- ZQBJRVYLUFBBEQ-UHFFFAOYSA-N 2-[diamino(3-formamidopropyl)azaniumyl]acetate Chemical compound [O-]C(=O)C[N+](N)(N)CCCNC=O ZQBJRVYLUFBBEQ-UHFFFAOYSA-N 0.000 description 6
- RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical class O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 6
- 229940073507 cocamidopropyl betaine Drugs 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 150000002402 hexoses Chemical class 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229940057950 sodium laureth sulfate Drugs 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000002338 glycosides Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229940073769 methyl oleate Drugs 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229940044591 METHYL GLUCOSE DIOLEATE Drugs 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000002194 synthesizing Effects 0.000 description 3
- ULUAUXLGCMPNKK-UHFFFAOYSA-L 2-sulfobutanedioate Chemical class OS(=O)(=O)C(C([O-])=O)CC([O-])=O ULUAUXLGCMPNKK-UHFFFAOYSA-L 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N Nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 210000003491 Skin Anatomy 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N Titanium isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- 238000004851 dishwashing Methods 0.000 description 2
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002884 skin cream Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N α-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-Butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 1
- DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- GDGUCRQNTDPGSD-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO.OCC(CO)(CO)CO GDGUCRQNTDPGSD-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- DFPSKSUPYBRMPF-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylpropane-1,3-diol Chemical compound OCC(C)(CO)CO.OCC(C)(CO)CO DFPSKSUPYBRMPF-UHFFFAOYSA-N 0.000 description 1
- IGDUBEZMULCNAF-UHFFFAOYSA-N 2-[(2-dodecylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCCCCC1=CC=CC=C1OCC1OC1 IGDUBEZMULCNAF-UHFFFAOYSA-N 0.000 description 1
- WNISWKAEAPQCJQ-UHFFFAOYSA-N 2-[(2-nonylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCC1=CC=CC=C1OCC1OC1 WNISWKAEAPQCJQ-UHFFFAOYSA-N 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N 2-stearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N 3-(2,3-dihydroxypropoxy)propane-1,2-diol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N 60-33-3 Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 229940063953 AMMONIUM LAURYL SULFATE Drugs 0.000 description 1
- BTBJBAZGXNKLQC-UHFFFAOYSA-N Ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 1
- PDNLXUROKBBMBE-BYOHNYAZSA-N CC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O Chemical compound CC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O PDNLXUROKBBMBE-BYOHNYAZSA-N 0.000 description 1
- 229960002788 CETRIMONIUM CHLORIDE Drugs 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M Cetrimonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 229960001927 Cetylpyridinium Chloride Drugs 0.000 description 1
- YMKDRGPMQRFJGP-UHFFFAOYSA-M Cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N D-sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N Heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 229940099367 LANOLIN ALCOHOLS Drugs 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 229960004488 Linolenic Acid Drugs 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 229940040461 Lipase Drugs 0.000 description 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 229940057981 STEARALKONIUM CHLORIDE Drugs 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N Sorbitan Chemical compound OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- SFVFIFLLYFPGHH-UHFFFAOYSA-M Stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-GDQSFJPYSA-N Sucrose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)[C@@]1(CO)[C@H](O)[C@@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-GDQSFJPYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000005227 alkyl sulfonate group Chemical group 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 230000003115 biocidal Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N butylene glycol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000003945 chlorohydrins Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- JZKFHQMONDVVNF-UHFFFAOYSA-N dodecyl sulfate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCCCCCCOS(O)(=O)=O JZKFHQMONDVVNF-UHFFFAOYSA-N 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 150000008195 galaktosides Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing Effects 0.000 description 1
- 229940023564 hydroxylated lanolin Drugs 0.000 description 1
- 229960004232 linoleic acid Drugs 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 102000004882 lipase Human genes 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 108090001060 lipase Proteins 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- ZHALDANPYXAMJF-UHFFFAOYSA-N octadecanoate;tris(2-hydroxyethyl)azanium Chemical compound OCC[NH+](CCO)CCO.CCCCCCCCCCCCCCCCCC([O-])=O ZHALDANPYXAMJF-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 229920004904 octoxynol-8 Polymers 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Polymers 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002335 preservative Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229940029614 triethanolamine stearate Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Abstract
Compositions comprising alkoxylated lipophilic polyol compounds, e.g., ethoxylated, esterified methyl glucosides, are disclosed wherein at least 5%of the polyol derivatives have about three moles of the lipophilic substituent per mole of polyol. Quite advantageously, the disclosed polyol derivatives can be dissolved into aqueous solutions to provide liquid thickeners suitable for thickening surfactant-containing compositions, e.g., shampoos, at cold processing temperatures.
Description
LIQUID THICKNESS FOR TENSITIVE SYSTEMS
Field of the Invention The present invention relates to alkoxylated lipophilic polyol compounds, having approximately three moles of lipophilic substituents per mole of polyol and, more specifically, to the use of such compounds as thickeners in liquid surfactant compositions.
BACKGROUND OF THE INVENTION Liquid compositions containing surfactants, for example shampoos, dishwashing liquids and other personal care and industrial products, traditionally contain thickeners, in order to have a viscosity of liquid compositions sufficient to enable convenient handling. Often, the thickeners comprise an alkoxylated polyol containing lipophilic substituents, for example, ethoxylated methyl glucose, esterified with a fatty acid. These thickeners are traditionally alkoxylated to a sufficient extent to provide solubility in water and provide a higher viscosity to the composition of the liquid surfactant. The lipophilic substituent, for example the fatty acid, typically supplies thickening characteristics associative to the thickener. Often, thickeners are introduced into liquid surfactant compositions in solid form and are mixed under conditions effective to dissolve the thickener in the liquid surfactant composition and cause significant increases in viscosity, for example, up to about 2,000. to 100,000 centipoises ("cP") or more. Frequently, the mixing must be conducted at elevated temperatures, for example from about 50 to 80 ° C, in order to promote the dissolution of the thickener and obtain the desired increase in viscosity (known in the art as the "hot process"). ). However, formulators of products comprising thickened liquids containing surfactants, for example, shampoos, desire the ability to formulate their products at ambient temperatures, for example from about 20 to 30 ° C (known in the art as the "cold process"). Additionally, the formulators also desire thickeners that can be introduced into the liquid compositions of surfactants, in the liquid form rather than in the solid form. The ability to introduce the thickener in a liquid form can provide a formulator with a higher degree of accuracy in introducing the correct amount of the thickener into the liquid surfactant system and also further facilitate the automatic process. Therefore, improvements compositions suitable for use as thickeners in liquid surfactant systems are convenient. Preferably, the thickeners can be introduced by the cold process and in the liquid state. Methods of using the compositions for thickening liquid compositions comprising surfactants are also convenient.
SUMMARY OF THE INVENTION By the present invention, the lipophilic, alkoxylated, eg, ethoxylated polyol compounds are provided with esterified methyl glycosides, which are useful, for example, as thickeners in systems containing liquid surfactants. In the compositions of the present invention, at least 5% by weight of the polyol compounds have about three moles of the lipophilic substituent per mole of the polyol. Very surprisingly, it has been found, according to the present invention, that, in the presence of a sufficient portion of the polyol compounds, having about three moles of the lipophilic substituent per mole of the polyol, the capacity of the composition can be increased. to thicken a liquid surfactant system, preferably at cold process temperatures. In addition, the present invention provides processes for preparing the compositions, which include the steps of alkoxylating the polyol with a suitable alkoxylation reagent, for example ethylene oxide, and introducing a lipophilic substituent, for example by esterification with a fatty acid. The processes also provide for the introduction of the lipophilic substituents before the alkoxylation step, as well as the sequential introduction of the lipophilic substituent and the alkoxylation reagent.
Detailed Description of the Invention Polyols suitable for use as starting materials, in accordance with the present invention, comprise any compound having three or more hydroxyl groups per molecule, which are reactive with the alkoxylation reagents, and the lipophilic reagents described below. General examples include glycerols, polyglycerols, sugar alcohols, for example sorbitol or sorbitan, and saccharides, for example glucose and its derivatives. More specific examples of the polyols, which can be used according to the invention, include, but are not limited to, trimethylolethane [2-methyl-2- (hydroxymethyl) -1,3-propanediol], trimethylolpropane [2-ethyl] -2- (hydroxymethyl) -1, 3-propanediol], pentaerythritol (2-ethyl-2- (hydroxymethyl-1,3-propanediol), pentaerythritol (2,2-dimethylol-1,3-propanediol), diglycerol (dimer) glycerol), dipenta-erythritol, glycerol, and the like Preferred polyol starting materials for use in accordance with the present invention are the glucose derivatives, more preferably, the glycosides, eg the glycosides, galactosides, monosaccharides, oligosaccharides having up to 10 repeating units of saccharides per molecule, and sucrose Especially preferred glycosides include the alkyl glucosides, such as, for example, methyl glucoside, ethyl glucoside, propyl glucoside, butyl glucoside and glucoside amyl, such polyols are commercially available. Suitable reagents for the alkoxylation of the polyols are the alkylene oxides, such as, for example, ethylene oxide, propylene oxide, butylene oxide and mixtures thereof. Other alkoxylation reagents, for example the higher alkylene oxides, can be used according to the present invention. Alkylene oxides suitable for use, according to the present invention, are commercially available. The amount of alkoxylation, according to the present invention, is that which is effective to provide the solubility in water and the viscosity in a liquid composition of the surfactant. Typically, these amounts vary from about 50 to 400, preferably from about 80 to 180 and, more preferably, from about 100 to 160 moles of the alkylene oxide per mole of the polyol. Methods for alkoxylating polyols, for example by direct alkoxylation, are known to those skilled in the art. Alternatively, methyl, partially alkoxylated glycosides, for example GLUCAM ™ E-20 (methyl glycoside of PEG-20), available from Amerchol Corporation, Edison, NJ, can be used as a starting material, which can then be used as a starting material. to be further alkoxylated, to contain the desired degree of alkoxylation. Suitable lipophilic reagents for deriving the polyols of the present invention include any compound that is reactive with the polyols and has a molecular weight sufficient to promote associative thickening, when introduced into a liquid system containing a surfactant. Typically, the lipophilic reagents comprise hydrocarbon or substituted hydrocarbon portions, with about 8 to 30, preferably about 12 to 26 and, more preferably, about 16 to 22 carbon atoms per molecule. The particular structure of the lipophilic reagents is not critical in the present invention and may, for example, be alkyl, aryl, alkylaryl, alkenyl, cyclic, branched or straight. Traditionally, the reactants are fatty acids, fatty esters, epoxides, halides, glycidyl ethers or oils of vegetable or animal origin. The reagents typically provide any ester or ether bond to the polyol. Stated otherwise, in the case of a glucose derivative, for example, the ether or ester is typically bound to the glucose derivative, indirectly through the polyoxyalkylene chain. Examples of suitable fatty acids include acids, natural or synthetic, saturated or unsaturated, which are linear or branched. The fatty acids can be used alone or as a mixture. Natural fatty acids include, for example, linear, saturated or unsaturated fatty acids, such as capric acid, enanthic acid, caprylic acid, pelargonic acid, decanoic acid, lauric acid, myristic acid, plamitic acid, stearic acid, linolic acid, oleic acid, capric acid and undecanic acid, which are traditionally obtained by hydrolyzing vegetable oils and animal oils, such as coconut oils, palm oil, linseed oil and soybean oil. Examples of synthetic fatty acids include fatty acids, linear or branched, prepared by oxidizing the olefinic polymers. It is also possible to use the fatty acids derived from microorganisms, such as, for example, α-linolenic acid. In addition, as the lower alkyl esters of the fatty acids, alkyl esters having from 1 to 8 carbon atoms, such as the methyl, ethyl or propyl esters of the fatty acids, described above can be used. The fatty acid esters of hexose or its alkyl glycoside can be synthesized using various known methods, including the synthesis of esters using lipase and the like; for example, (1) the ester exchange reaction between the starting oils or fat and a hexose or its alkyl glycoside, (2) an ester exchange reaction between a lower alkyl ester of a fatty acid and a hexose or its alkyl glycoside, or (3) a synthesis of esters between a fatty acid and a hexose or its alkyl glycoside. In addition, a synthesis process, which uses a fatty acid chloride and a hexose or its alkyl glycoside, may also be employed. Examples of other suitable lipophilic reagents include the glycidyl ethers, for example the nonylphenylglycidyl ether or the dodecylphenyl glycidyl ether, alpha-olefin epoxides, for example the 1,2-epoxyhexadecane and their respective chlorohydrins, or alkyl halides, for example, dodecyl bromide, and vegetable and animal oils, mentioned above. Halogenated fatty acid products can also be used as lipophilic reagents. The amount of the lipophilic reagent used to derive the polyols of the present invention is preferably effective to promote the associative thickening performance of the polyol derivatives, when present in a liquid surfactant composition. Typically, the level of the average substitution is about 3, for example from 2.5 to 4, preferably from about 2.5 to 3.9 and, more preferably, from about 2.8 to 3.6 moles per mole of the polyol. Details relating to the derivatization of the polyols to include the lipophilic substituents are known to those skilled in the art. The average amount of the lipophilic substituent per mole of polyol
(referred to in the art as the Degree of Substitution, "DS") can be determined by any technique known to those skilled in the art, for example, by nuclear magnetic resonance ("NMR") spectroscopy. Lipophilic reagents suitable for use in accordance with the present invention are commercially available. In accordance with the present invention, the alkoxylated lipophilic polyol compounds comprise a mixture of substituted compounds with various amounts of the lipophilic substituent, depending on the hydroxyl groups available in the starting material of the polyol. At least 5% of the polyol compounds in the composition have about three moles of the lipophilic substituent per mole of the polyol. For example, in the case of an esterified, ethoxylated methyl glucoside, at least 5% of the compounds are substituted with about three moles of the lipophilic substituent per mole of the methyl glucoside. Typically, at least 25%, preferably at least 50% and, more preferably, at least 75% of the polyol derivatives in the composition, have about three moles of the lipophilic substituent per mole of the polyol. Typically, the remainder of the composition comprises polyol derivatives having one, two or four moles of the lipophilic substituent per mole of the polyol. Traditionally, less than about 75%, preferably less than 50%, and, more preferably, less than 25%, of the polyols in the composition, comprise one, two or four moles of the lipophilic substituent, per mole of the polyol. The sequence in which the alkylene oxide and the lipophilic substituents are reacted in the polyol is not critical in the present invention. In one aspect of the invention, the alkoxylation reaction is conducted first, followed by the substitution of the lipophilic substituent on the polyol. In another aspect of the invention, the polyol is first substituted with the lipophilic substituent, followed by the alkoxylation. In yet another aspect of the invention, the polyol is partially esterified, for example, to comprise one or two moles (on average) of the lipophilic substituent per mole of the polyol, then it is ethoxylated, then subsequently esterified, for example to comprise about three moles of the lipophilic substituent per mole of the polyol. Alternatively, the polyol can be partially ethoxylated, esterified and then ethoxylated back to the desired level. Also, the starting material may be the polyol, a partially alkoxylated polyol or a polyol that is partially reacted with the lipophilic reagent, or both. The derivatizations are typically conducted under a subatmospheric pressure, for example around 0.001 to 1.0 atmospheres, and at a temperature in the approximate range of 110 to 180 ° C during the alkoxylation stage and around 120 to 200 ° C for the stage of lipophilic substitution. The catalysts may or may not be used for derivatizations. However, typically, the catalysts are used to increase the rate of the reaction. The catalysts can be acidic, basic or neutral. Preferred catalysts for the alkoxylation step include Na, NaOCH3, KOH, NaOH, K2C03, Na2C03.
Preferred catalysts for the lipophilic substitution stage include Na 2 CO 3, KOH, NaOH, acids, including p-toluenesulfonic acid ("p-TSA"), H 2 SO 4, HCl, and others, including organic titanates, for example titanate of tetraisopropyl, available as Tyzor ™, catalyst from the DuPont Company, Wilmington, DE. Further details relating to the manufacture of the alkoxylated lipophilic polyol compounds are known to those skilled in the art and are described, for example, in US Patents Nos. 4,687,843, 5,109,127, 5,501,813 and 5,502,175. The product produced from the derivatization reactions is typically in the form of a solid, granulate or powder. The solid product is suitable for packaging and transport to customers. In a preferred aspect of the invention, the lipophilic, alkoxylated polyol derivatives are dissolved in a suitable solvent to supply a liquid thickener suitable for use in viscosifying liquid compositions containing surfactants. Any suitable liquid, capable of dissolving the polyol derivatives, is suitable for use, according to the present invention. Preferably, the liquids are aqueous, with or without additional liquids miscible in water. For example, suitable solvents include alkylene glycols having about 2 to 5 carbon atoms per molecule, such as propylene glycol, ethylene glycol, butylene glycol, propane diol and butane diol. Other solvents, such as, for example, polyalkylene glycols, for example the fluids CABOWAX ™ PEG and UCON ™, available from Union Carbide Corporation, Danbury, CT, may also be employed. When the product is provided in a liquid form, it typically comprises from about 20 to 60%, preferably from 30 to 50% of the polyol derivative, with the remainder being the liquid solvent and any desired additive, such as, for example, preservatives , biocides, etc., which are generally present in minor amounts, for example less than about 5% by weight, based on the total weight of the liquid composition. Further, when in liquid form, it is preferred that the liquid containing the thickener have a viscosity which is sufficiently low to allow the liquid to be pumped or emptied without difficulty. Typically, the viscosity is less than about 6,000 cP, preferably less than about 4,000 cP. As used herein, the term viscosity means the viscosity measured with a Viseosí etro Broo field, with a suitable axis and speed of rotation, as determined by a person skilled in the art, for example axis 6 at 10 rpm.
In a preferred aspect of the invention, when the polyol is a glucose derivative, the liquid composition comprises approximately 10 to 30% by weight of water, and approximately 30 to 50% by weight of the propylene glycol and approximately 30% by weight. to 50% of the glucose derivative. An especially preferred composition comprises about 20% by weight of water, about 40% by weight of propylene glycol and about 40% by weight of the glucose derivative. The lipophilic, alkoxylated polyol derivatives of the present invention have a variety of end-use applications, such as, for example, personal care applications and industrial applications. Typical personal care applications include, for example, pharmaceutical and cosmetic compositions, such as, for example, shampoos, conditioners, ointments, skin creams, lotions, soaps and the like. Typical industrial applications include, for example, the use as viscosity adjusters for fluid handling in general and for surfactant applications, such as dishwashing liquids, laundry detergents, suspension aids, as adhesion promoters. and coating materials. In one aspect of the invention, the alkoxylated lipophilic polyol derivatives are used to thicken liquid compositions, comprising one or more surfactants. Exemplary surfactants may include: anionic agents, including fatty acid soaps, alkyl sulfates, alkyl ether sulfates, alkyl or aryl sulfonates, sulfosuccinates, sarcosinates, alkyl glucose esters or their alkoxylates and, in particular , sodium lauryl sulfate, ammonium lauryl sulfate, triethanolamine lauryl sulfate, sodium laureth sulfate, alpha-olefin sulfonate, disodium laureth sulphosuccinates, triethanolamine stearate; nonionics, which include methyl glucose esters or their alkoxylates, fatty acid alkanol amides, polyglycol ethers or their alkyl or aryl derivatives, hydroxylated lanolin, lanolin alcohols and in particular olet-20 , cetearet-20, methyl glucose dioleate, methyl glucose stearate, glycerol monostearate, cocoyl diethanolamine, nonoxal-7, and octoxynol-8; cationics, which include trimethyl-alkyl ammonium salts, quaternized ethylene diamine amides, alkyl pyridinium salts and, in particular, cetrimonium chloride, stearalkonium chloride and cetyl pyridinium chloride; and amphoteric, which include the alkyl β-aminopropionates, betaines, alkyl imidazolines and, in particular, cocoanfocarboxy glycinate, cocamidopropyl betaine and caproanfocarboxy propionate.
In this aspect of the invention, a first liquid, comprising the alkoxylated lipophilic polyol compounds, is combined with a second liquid, comprising a surfactant under mixed conditions, in order to provide an increase in viscosity of at least 10%, preferably at least 50%, more preferably at least 100% and especially preferred at least 200%. As used herein, the term "Viscosity Increase" means the increase in viscosity, expressed as a percentage, in a liquid composition containing a surfactant, among the lipophilic, alkoxylated polyol compounds of the present invention, compared with the lipophilic, alkoxylated polyol compounds in which a substantial fraction, for example at least 90% of the compounds have about two moles, ie from 1.5 to 2.5 moles, of the lipophilic substituent per mole of the polyol. For the measurement of the Viscosity Increase, the mixture of the surfactant system is conducted at a temperature sufficient to dissolve the components, for example from the ambient to about 80 ° C, with suitable mixing (preferably without the formation of foam) during some 2 to 3 hours. To determine the Increase in Viscosity, the lipophilic, alkoxylated polyol is used in the liquid composition of the surfactant at an active concentration of about 0.1 to 5% by weight, preferably 0.1 to 1% by weight, based on the total weight of the liquid composition of the agent surfactant. For comparison purposes, the active concentration must be essentially the same. For this measurement, a Brookfield RVT viscometer with an axis No. 6, at 10 rpm, is generally adequate. The viscosity measurement must be taken at a fixed temperature, for example 22.5 ° C. Likewise, the comparison should be made using polyol derivatives having similar alkylene oxide substitution levels, for example within ± 30 units of alkylene oxide, and a similar lipophilic substituent, for example within ± 2 carbon atoms per molecule. A preferred surfactant composition for determining the Increase in Viscosity, comprises the following combined ingredients, as described below.
Ingredients% by weight Deionized water q.s. for 100 Sodium laureth sulfate-2 40.00 (26% active Cocamidopropyl betaine 11.50 (35% active weight) DMDM hydantoin 0. Thickener (polyol compound 1.25 to 40% by weight, propylene glycol 40% by weight, water 20% by weight Procedure: Add the sodium laureth sulfate -2 and the cocamidopropyl betaine to the water in order, one at a time, until it is completely uniform, before adding the next ingredient, once in a uniform state, add the Thickener and stir and heat to 70 ° C. When this thickener dissolves completely, begin to cool the system to 40 ° C. At 40 ° C add the DMDM hydantoin and continue cooling to room temperature Record the viscosity after 24 hours It has been found very advantageously, according to the present invention, that personal care products, for example shampoos, skin creams and the like, can provide the following desirable characteristics. e shampoos and other hair care products can be obtained: improved rinsing capacity, good touch, foam formation, combined potential, synergy with other ingredients, clarity and tolerance to salt. In the case of skin care products, it is possible to obtain: improved properties against irritations, fatty agents, wetting and dermatological compatibility. A typical cleansing formulation for the skin or hair, comprising the lipophilic, alkoxylated polyol compounds of the present invention, may contain the following ingredients and may be prepared as described below. Ingredients% by weight Deionized water q.s. Polyquaternium-10 0.20 Sodium laureth sulfate 40.00 (26% active weight) Cocamidopropyl betaine 11.50 (35% active weight) Disodium laureth sulphosuccinate 5.00 (40% active weight) Thickener (composed of 0.50 polyol 40% by weight , propylene glycol at 40% by weight, 20% by weight of water) DMDM hydantoin 0.40
Procedure: Add polyquaternium-10 to deionized water at room temperature, with adequate agitation. When uniform, heat to 70 ° C and mix until completely hydrated. Once completely hydrated, add the remaining ingredients to the DMDM hydantoin, one at a time, in order, wait until each one dissolves before adding the next. Allow to cool to 40 ° C. When it reaches 40 ° C, add the DMDM hydantoin. Continue cooling to room temperature.
EXAMPLES The following examples are provided for illustrative purposes, and no attempt is made to limit the scope of the claims that follow. In the examples, the amounts mentioned are given in percent by weight, unless otherwise indicated.
EXAMPLE 1 (Comparative) PREPARATION OF THE MIXTURE OF METHYL-GLUCOSE DIOLEATE OF PEG-120-PG-WATER A sample of methyl glucose dioleate PEG-120 (available from Amerchol Corporation, Edison, NJ, under the trade name Glucamate ™ DOE-120) of 1000 grams ("g"), was placed in a flask equipped for stirring and heating. To this were added - 1000 g of propylene glycol and 500 g of water. The mixture was heated to 60 ° C, with stirring. By melting and with continued agitation, the dissolved solids and the solution became fluid and transparent. The final liquid product was then allowed to cool to room temperature. The product had a viscosity of < 2000 cP at room temperature.
EXAMPLE 2 PREPARATION OF THE METHYL-GLUCOSIDE TRIOLEATE MIXTURE OF PEG-100-PG-WATER In a 1 liter pressure reactor, 192 g of methyl glycoside PEG-20 (Glucam ™ E-20, available from Amerchol 'Corporation, Edison, NJ). To this was added 1 g of KOH flakes. The container was closed and the vacuum increased as the temperature increased to 140 ° C. The material was stirred and dried at 140 ° C and a pressure of about 10 mm Hg, for 0.5 hour. The system was purged three times with nitrogen and pressurized to 1.75 kg / cm2. The liquid was ethoxylated with 630 g of ethylene oxide at 140-145 ° C and at 4.55 kg / cm2. After the addition was complete, the reaction mixture was digested for one hour and purged with nitrogen to remove any residual oxide. This gave a white, hard, waxy material at room temperature of the polyoxyethylene-100 methyl glucoside. A sample of the methyl glycoside from PEG-100 above (476 g) was placed in a flask and heated to about 50 ° C until all the material melted. Oxalic acid (4.4 g) was added in a small amount of water. The mixture was stirred for about 0.5 hour and then dried under vacuum, i.e., about 10 mm of mercury ("mm Hg") at 110 ° C.
The vacuum was interrupted with nitrogen. Then the methyl oleate (101 g) was added. The system was then purged with nitrogen. A low level of vacuum was developed
(~ 600 mm Hg). Using a syringe, 6.3 g of the catalyst (tetraisopropyl titanate, Tyzor ™ from Dupont) were introduced and the mixture was stirred for 10 minutes. The temperature was then increased to approximately 150 ° C. During the next 5 hours, the vacuum was gradually increased to 200 mm Hg. At that point, the reaction was completed and the temperature reduced to approximately 65 ° C. The vacuum was interrupted and 50 g of water was added to decompose the catalyst. The mixture was stirred at 50 ° C for 1 hour. The pH was adjusted to 6-7 with aqueous oxalic acid and then dried under high vacuum (<5 mm Hg) and 110 ° C, for 0.5 hour. The product was a brown waxy solid, which had the following analysis:
Parameter pH value (10% in water) 6.9 Acid value 0.6 Saponification value 37.0 Hydroxyl value 14.0
The mixture was cooled to 80 ° C, according to a solution of 566 g of propylene glycol and 283 g of water was added with stirring. This mixture was stirred for 0.5 hour, while allowing to cool. This gave a light brown solution / mixture and had a viscosity of approximately 2000 cP.
EXAMPLE 3 PREPARATION OF THE METHYL GLUCOSE TRIOLEATE MIXTURE
PEG-120-PG-WATER Under a nitrogen atmosphere, one reactor was charged with 42 g of methyl oleate and 0.8 g of SAG-10 (anti-foaming agent from Witco Corp., Greenwich, CT). Then one thousand grams of the unneutralized Glucamate ™ DOE-120 was added. A nitrogen purge was placed in the upper space and the mixture was heated to 175 ° C. A low vacuum was applied slowly, that is, around 140 mm Hg, when the temperature reached about 150 ° C. Once the reaction mixture reached 75 ° C, the temperature stayed there. After about an hour, the upper space purge was changed to a spray. The vacuum was then slowly increased to about 5 mm Hg. The mixture was reacted for an additional 5 hours. Near the end of the cooking time, a sample was removed for the analysis of methyl oleate by gas chromatography. The residual methyl oleate decreased to approximately 0.4% (weight loss) and the reaction was cooled to about 80 ° C, the nitrogen spray was closed, the vacuum was stopped with nitrogen and the product was neutralized with an aqueous solution containing 0.6 g of tartaric acid. The mixture was analyzed in pH, color, hydroxyl number and acid value and viscosity performance. The analysis of the product, methyl glucose trioleate PEG-120, showed:
Viscosity performance 65, 000 cP Hydroxyl value 10 Color GH 7 pH (10% in water) 6.5 Acid value 0.8
To prepare the mixture, 1033 g of propylene glycol (PG) was added to the hot product (70-80 ° C). the methyl glucose trioleate of PEG-120 base, prepared above. After the PG was completely mixed, the heating was discontinued and 517 g of deionized water was added. The mixture was stirred for about 20 minutes to ensure a uniform solution, from which a sample was taken and analyzed for pH,% PG and% water. The product solution was then cooled to about 40 ° C and stored. The mixture had the following analysis:
Water 20% Propylene Glycol 40% pH (10% solids) 6.5
* The Performance Viscosity method as in Example # 4 (Viscosity Measurement).
EXAMPLE 4 MEASUREMENT OF VISCOSITY Liquid products, similar to those prepared in Examples C-1, 2 and 3, were tested in a liquid containing a surfactant, to determine the Increase in Viscosity. The formulation and procedure used are as follows:
Procedure: Add sodium laureth sulfate -2 and cocamidopropyl betaine to water, in order, one at a time, until complete uniformity, before adding the next ingredient. Once uniform, add the thickener with stirring and heat to 70 ° C. When the thickener completely dissolved, start the cooling system at 40 ° C. Add the DMDM hydantoin at 40 ° C and continue to cool to room temperature. The viscosity was recorded after 24 hours. Viscosity was measured using a viscometer
Brookfield RVT with a No. 6 shaft at 10 rpm.
Thickener Example Viscosity, cP Increase in Viscosity,% ___ 13,500 = 2 56,000 315 3 65,000 381
EXAMPLE 5 PREPARATION OF THE BODY CLEANING FORMULA A cleaning formula for the body was prepared according to the following composition and procedure.
Procedure: Add polyquaternium-10 to deionized water at room temperature, with adequate agitation. When it reaches the uniform state, heat to 70 ° C and mix until hydrated completely. Once hydrated completely, add the remaining ingredients to the DMDM hydantoin, one at a time, in order, waiting until each one dissolved, before adding the next one.
Allow to cool to 40 ° C. Add the DMDM hydantoin at 40 ° C. Continue cooling to room temperature. The body cleaning formula had a viscosity of 40,500 cP, measured using a Brookfield RVT viscometer with a No. 6 shaft at 10 rpm. Without the thickener, the formula 'had a viscosity of 3,400 c.
EXAMPLE 6 COLD PROCESS A liquid product, similar to that prepared in Example 2, was tested in a liquid containing a surfactant at room temperature to evaluate the properties of the cold process. The formulation and procedure used were as follows.
Procedure: Sodium laureth sulfate -2, cocamidopropyl betaine and DMDM hydantoin were added to the water in order, one at a time, until complete uniformity, before adding the next ingredient. Once the uniformity was reached, the thickener was added, with stirring, at room temperature and continued to visually observe a response in the thickening (increase in viscosity). The mixture continued until completely uniform. Although the invention was described above with respect to specific aspects, those skilled in the art will recognize that other aspects are intended to be included within the scope of the claims that follow.
Claims (20)
- CLAIMS 1. A composition comprising alkoxylated glucose derivatives, having lipophilic substituents, in which at least 25% by weight of the glucose derivatives have from about 2.8 to 3.9 moles of said lipophilic substituents per mole of glucose.
- 2. The composition of claim 1, comprising an effective amount of glucose derivatives, having from about 2.8 to 3.9 moles of said lipophilic substituents per mole of glucose, to provide an increase in viscosity of at least 10%.
- 3. The composition of claim 1, comprising an effective amount of glucose derivatives, which with about 2.8 to 3.9 moles of said lipophilic substituents per mole of glucose, to provide an increase in viscosity of at least 50%.
- 4. The composition of claim 2, wherein at least 50% by weight of the glucose derivatives have about 2.8 to 3.9 moles of said lipophilic substituents per mole of glucose.
- 5. The composition of claim 1, wherein less than 75% of the glucose derivatives have one, two or four or more moles of the lipophilic substituents per mole of glucose.
- 6. The composition of claim 1, wherein the lipophilic substituents are linked to the glucose derivatives by an ester linkage or by an ether linkage.
- 7. The composition of claim 1, wherein the lipophilic substituents have about 8 to 30 carbon atoms per molecule.
- 8. The composition of claim 1, wherein the glucose derivatives are substituted with about 50 to 400 moles of alkylene oxide per mole of glucose.
- 9. The composition of claim 8, wherein the alkylene oxide is selected from the group consisting of ethylene oxide, propylene oxide and mixtures thereof.
- 10. The composition of claim 1, wherein the glucose derivative is selected from the group consisting of methyl glucoside, ethyl glucoside, propyl glucoside, butyl glucoside, amyl glucoside, and mixtures thereof.
- 11. The composition of claim 1, further comprising an alkylene glycol.
- 12. The composition of claim 11, which is in a liquid form.
- 13. A process for obtaining alkoxylated glucose derivatives, which comprises lipophilic substituents, in which at least 25% by weight of the glucose derivatives have about 2.8 to 3.9 moles of said lipophilic substituents per mole of glucose, this process comprises: (i) ) contacting a glucose derivative with an alkylene oxide, under effective reaction conditions to form an alkoxylated glucose intermediate, substituted with the alkylene oxide; and (ii) contacting the alkoxylated glucose intermediate with a lipophilic reagent, under effective reaction conditions to form the alkoxylated glucose derivative, comprising lipophilic substituents, wherein at least 25% by weight of the glucose derivative has approximately from 2.8 to 3.9 moles of said lipophilic substituents per mole of glucose.
- 14. The process of claim 13, wherein at least one of step (i) or step (ii) is conducted in the presence of a catalyst, selected from the group consisting of acid catalysts, basic catalysts and neutral catalysts.
- 15. The process of claim 13, wherein the lipophilic reagent is selected from the group consisting of fatty acids, fatty esters, epoxides, halides, glycidyl ethers, oils of vegetable and animal origin, and mixtures thereof.
- 16. A process for obtaining alkoxylated glucose derivatives, comprising lipophilic substituents, in which at least 25% by weight of the glucose derivatives have from about 2.8 to 3.9 moles of said lipophilic substituents per mole of glucose, this process comprises: (i) ) contacting a glucose derivative with a lipophilic reagent, under effective reaction conditions to form a lipophilic glucose intermediate, including lipophilic substituents, wherein at least 25% by weight of the glucose derivative has from about 2.8 to 3.9 moles of the lipophilic substituent per mole of glucose; (ii) contacting the lipophilic glucose intermediate with an alkylene oxide, under effective reaction conditions to form the alkoxylated glucose derivative.
- 17. A process for obtaining alkoxylated glucose derivatives, comprising lipophilic substituents, in which at least 25% by weight of the glucose derivatives have from about 2.8 to 3.9 moles of said lipophilic substituents per mole of glucose, this process comprises: (i) ) contacting a glucose derivative with a lipophilic reagent, under effective reaction conditions to form a lipophilic glucose intermediate, comprising lipophilic substituents, in which at least 75% by weight of the glucose derivative has two moles of said lipophilic substituent, per mole of glucose; (ii) contacting the lipophilic glucose intermediate with an alkylene oxide, under effective reaction conditions to form an alkoxylated, lipophilic glucose intermediate substituted with the alkylene oxide; and (iii) contacting the lipophilic, alkoxylated glucose intermediate with a lipophilic reagent, under effective reaction conditions to form the alkoxylated glucose derivative, including lipophilic substituents, wherein at least 25% by weight of the glucose derivative it has about 2.8 to 3.9 moles of said lipophilic substituent per mole of glucose.
- 18. A method for thickening a liquid composition, including a surfactant, this method comprises contacting, under the mixing conditions, one or more lipophilic polyol compounds, alkoxylated, with a second liquid, comprising a surfactant; characterized in that (i) this one or more lipophilic, alkoxylated polyol compounds are present in the liquid form; e (ii) at least 25% by weight of this one or more lipophilic polyol compounds, alkoxylated, are substituted with about 2.8 to 3.9 moles of a lipophilic substituent per mole of the polyol, to provide an increase in viscosity of at least the 10%.
- 19. The method of claim 18, wherein the lipophilic, alkoxylated polyol compound is derived from a polyol, selected from the group consisting of glucose, sorbitol, glycerol, polyglycerols, and mixtures thereof.
- 20. The method of claim 19, wherein the increase in viscosity is at least 100%.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US60/090,324 | 1998-06-23 |
Publications (1)
Publication Number | Publication Date |
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MXPA00012657A true MXPA00012657A (en) | 2001-12-13 |
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