WO1995019416A1 - Wässrige lösungen von quaternierten fettsäuretriethanolaminester-salzen - Google Patents
Wässrige lösungen von quaternierten fettsäuretriethanolaminester-salzen Download PDFInfo
- Publication number
- WO1995019416A1 WO1995019416A1 PCT/EP1995/000047 EP9500047W WO9519416A1 WO 1995019416 A1 WO1995019416 A1 WO 1995019416A1 EP 9500047 W EP9500047 W EP 9500047W WO 9519416 A1 WO9519416 A1 WO 9519416A1
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- WIPO (PCT)
- Prior art keywords
- aqueous solutions
- fatty acid
- ester salts
- weight
- esters
- Prior art date
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- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 51
- 239000000194 fatty acid Substances 0.000 title claims abstract description 51
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 51
- -1 fatty acid triethanolamine ester salts Chemical class 0.000 title claims abstract description 29
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 21
- 150000002148 esters Chemical class 0.000 claims abstract description 33
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 239000000243 solution Substances 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 2
- 238000007046 ethoxylation reaction Methods 0.000 claims description 2
- 239000002979 fabric softener Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 8
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 3
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 235000021357 Behenic acid Nutrition 0.000 description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 2
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 229940116226 behenic acid Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 229960002446 octanoic acid Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- CNVZJPUDSLNTQU-SEYXRHQNSA-N petroselinic acid Chemical compound CCCCCCCCCCC\C=C/CCCCC(O)=O CNVZJPUDSLNTQU-SEYXRHQNSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- CUXYLFPMQMFGPL-UHFFFAOYSA-N (9Z,11E,13E)-9,11,13-Octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCCCCC(O)=O CUXYLFPMQMFGPL-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- OXEDXHIBHVMDST-UHFFFAOYSA-N 12Z-octadecenoic acid Natural products CCCCCC=CCCCCCCCCCCC(O)=O OXEDXHIBHVMDST-UHFFFAOYSA-N 0.000 description 1
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000017274 Diospyros sandwicensis Nutrition 0.000 description 1
- 241000282838 Lama Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- CNVZJPUDSLNTQU-UHFFFAOYSA-N Petroselaidic acid Natural products CCCCCCCCCCCC=CCCCCC(O)=O CNVZJPUDSLNTQU-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 229940081733 cetearyl alcohol Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000000750 constant-initial-state spectroscopy Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- 230000005226 mechanical processes and functions Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229920002601 oligoester Polymers 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000176 sodium gluconate Substances 0.000 description 1
- 229940005574 sodium gluconate Drugs 0.000 description 1
- 235000012207 sodium gluconate Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- AQWHMKSIVLSRNY-UHFFFAOYSA-N trans-Octadec-5-ensaeure Natural products CCCCCCCCCCCCC=CCCCC(O)=O AQWHMKSIVLSRNY-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- 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
- C09K23/18—Quaternary ammonium compounds
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/45—Derivatives containing from 2 to 10 oxyalkylene groups
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/08—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/835—Mixtures of non-ionic with cationic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
- C11D3/0015—Softening compositions liquid
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/667—Neutral esters, e.g. sorbitan esters
Definitions
- the invention relates to aqueous solutions of quaternized fatty acid triethanolamine ester salts containing fatty acid oligoglycerol esters as thickeners, agents containing these components and the use of fatty acid oligoglycerol esters as thickeners for aqueous solutions of quaternized fatty acid triethanolamine ester salts.
- Quaternized fatty acid triethanolamine ester salts so-called “esterquats” have become increasingly important in recent years as ecotoxicologically safe raw materials for fabric softeners.
- the products are usually marketed as alcoholic concentrates and are diluted with water by the manufacturers of conditioning agents to a user concentration which, depending on requirements, can be in the range from 1 to 50% by weight of solids.
- Viscosity problems arise both in the production of ester quat concentrates and in the formulation of the aqueous compositions which can contain these cationic surfactants in different amounts.
- Esterquat concentrates with a solids content of approximately 80 to 90% by weight are viscous and require regulators to reduce the viscosity.
- EP-A2 0 165 138 proposes the use of organic salts such as sodium gluconate or short-chain quaternary ammonium salts.
- organic salts such as sodium gluconate or short-chain quaternary ammonium salts.
- ester quats based on unsaturated fatty acids, quaternized fatty acid amidoamine salts, long-chain QAV and diquaternized fatty acid triethanola inester salts are also suitable for this purpose.
- the object of the invention was therefore to provide aqueous solutions of quaternized fatty acid triethanolamine ester salts with improved viscosity behavior.
- the invention relates to aqueous solutions of quaternized fatty acid triethanolamine ester salts, which are characterized in that they are, if appropriate, 0.01 to 0.1, preferably 0.01 to 0.03% by weight, based on the solutions, as viscosity regulators contain alkoxylated esters of fatty acids with technical oligoglycerol mixtures.
- fatty acid oligoglycerol esters and alkoxylated fatty acid oligoglycerol esters are particularly suitable as thickeners for aqueous solutions of esterquats.
- the viscosity of the aqueous solutions can easily be raised to a value which enables easy metering.
- the invention includes the knowledge that the products are stable in storage, i.e. the viscosity level which has been set remains practically unchanged even after prolonged storage.
- the fact that the fatty acid oligoglycerol esters are only effective as a thickener in the range of very low concentrations is also particularly surprising.
- Quaternized fatty acid triethanolamine ester salts are known substances which can be obtained by the relevant methods of preparative organic chemistry.
- ester quats are known substances which can be obtained by the relevant methods of preparative organic chemistry.
- esterquats as softening agents for textiles has been described, for example, in the review articles by O.Ponsati in CR CED-Kongress, Barcelona, 167 (1992) and R.Puchta in CR CED-Kongress, Sitges, 59 (1993).
- R --- C0 for an acyl radical with 6 to 22 carbon atoms
- R2 and R 3 independently of one another for hydrogen or R --- C0
- R ⁇ for an alkyl radical with 1 to 4 carbon atoms or a (CH2CH2 ⁇ ) gH- Group
- m, n and p in total for 0 or numbers from 1 to 12, q for numbers from 1 to 12 and X for halide, alkyl sulfate or alkyl phosphate.
- ester quats which can be used in the context of the invention are products based on capric acid, caprylic acid, capric acid, lauric acid, myristic acid, Palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, arachic acid, behenic acid and erucic acid as well as their technical mixtures, such as are obtained, for example, in the pressure release of natural fats and oils.
- industrial Ci2 be l8 ⁇ co ⁇ os f ⁇ ETT acids unc - in particular, partly hydrogenated Ci5 ⁇ g tallow or palm oil fatty acids and elaidic acid-rich CISS / ig fatty cuts used.
- the fatty acids and the triethanolamine can be used in a molar ratio of 1.1: 1 to 3: 1 to produce the quaternized esters.
- an application ratio of 1.2: 1 to 2.2: 1, preferably 1.5: 1 to 1.9: 1 has proven to be particularly advantageous.
- the preferred esterquats are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9 and are derived from technical Cissig tallow or palm fatty acid (iodine number 0 to 40).
- quaternized fatty acid triethanolamine ester salts of the formula (I) have proven to be particularly advantageous in which R --- CO for an acyl radical having 16 to 18 carbon atoms, R 2 for R --- C0, R 3 for hydrogen, R 4 for a methyl group, m, n and p for 0 and X for methyl sulfate.
- Esterquats are usually marketed as alcoholic concentrates with a solids content of approx. 80 to 90% by weight.
- the aqueous solutions claimed to be thickened in the sense of the invention usually have Usually a solids content in the range of 1 to 50, preferably 3 to 15 wt .-%.
- Possible viscosity regulators are alkoxylated esters of fatty acids with technical oligoglycerin chemicals and their addition products of an average of 1 to 10 and preferably 2 to 5 mol of alkylene oxide, which have long been known as such.
- the viscosity regulators are preferably optionally alkoxylated esters which are derived from fatty acids of the formula (II)
- R ⁇ CO stands for an aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms and 0 and / or 1 to 3 double bonds.
- Typical examples are esters of oligoglycerol mixtures with caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, Isotridecan Text- acid, myristic acid, palmitic acid, palmoleic, re Stearinkla ⁇ , isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, eleostearic acid, arachidonic acid, gadoleic , Behenic acid and erucic acid and their technical mixtures, which are used, for example, in the pressure splitting of natural fats and oils, the reduction of aldehydes from Roelen's oxosynthesis or the dimerization of unsaturated fatty acids.
- the viscosity regulators are preferably alkoxylated esters, which are also derived from industrial oligoglycerol mixtures of the formula (III),
- Typical examples are fatty acid esters with technical oligoglycerol mixtures which have an average degree of self-condensation in the range from 1.5 to 10, preferably 2 to 5.
- Fatty acid esters based on oligoglycerol mixtures with a high content of di- and triglycerol are particularly preferred.
- the viscosity regulators are preferably optionally alkoxylated fatty acid oligoglycerol esters which finally have an average degree of esterification of 0.75 to 4. Although the products are generally mixtures of mono-, di-, tri- and optionally oligoesters due to the preparation, those viscosity regulators which have a statistical average of 1 to 3 ester groups are particularly preferred.
- the alkoxylated esters are preferably addition products of ethylene oxide.
- the degree of ethoxylation of the esters is usually in the range from 1 to 10 and in particular 2 to 5.
- diesters of isostearic acid with technical triglycerol are used as viscosity regulators in quantities of 0.01 to 0.03% by weight, based on the solutions.
- aqueous solutions according to the invention are characterized by an advantageous viscosity which is practically unchanged even after prolonged storage.
- the invention further relates to aqueous laundry softening agents containing 1 to 50% by weight of quaternized fatty acid triethanolamine ester salts, 0.01 to 0.1% by weight of optionally alkoxylated esters of fatty acids with technical oligoglycerol mixtures and, if appropriate, others Auxiliaries and additives.
- the invention further relates to aqueous hair treatment compositions containing 1 to 50% by weight of quaternized fatty acid triethanolamine ester salts, 0.01 to 0.1% by weight. optionally alkoxylated esters of fatty acids with technical oligoglycerol mixtures and optionally further auxiliaries and additives.
- the invention relates to the use of optionally alkoxylated esters of fatty acids with technical oligoglycerol mixtures as viscosity regulators for aqueous solutions of quaternized fatty acid triethanolamine ester salts, in which they are present in amounts of 0.01 to 0.1% by weight. -% - based on the solutions - may be included.
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Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7518816A JPH09508106A (ja) | 1994-01-14 | 1995-01-05 | 第四級化脂肪酸トリエタノールアミンエステル塩の水溶液 |
EP95906310A EP0739409A1 (de) | 1994-01-14 | 1995-01-05 | Wässrige lösungen von quaternierten fettsäuretriethanolaminester-salzen |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4400927A DE4400927A1 (de) | 1994-01-14 | 1994-01-14 | Wäßrige Lösungen von quaternierten Fettsäuretriethanolaminester-Salze |
DEP4400927.5 | 1994-01-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995019416A1 true WO1995019416A1 (de) | 1995-07-20 |
Family
ID=6507921
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1995/000047 WO1995019416A1 (de) | 1994-01-14 | 1995-01-05 | Wässrige lösungen von quaternierten fettsäuretriethanolaminester-salzen |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0739409A1 (de) |
JP (1) | JPH09508106A (de) |
DE (1) | DE4400927A1 (de) |
WO (1) | WO1995019416A1 (de) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0754215B1 (de) * | 1994-04-07 | 2001-05-23 | Unilever Plc | Gewebeweichmacherzusammensetzung |
EP0762830B1 (de) * | 1994-06-02 | 2001-12-19 | Kao Corporation | Methode zur Wirkungssteigerung von Agrarchemikalien |
EP2576743B1 (de) | 2010-05-28 | 2015-11-11 | Colgate-Palmolive Company | Fettsäurekettensättigung bei einem esterquat auf alkanolaminbasis |
WO2018219997A1 (en) | 2017-05-30 | 2018-12-06 | Roche Diagnostics Gmbh | Catalysts for reversing formaldehyde adducts and crosslinks |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19756434A1 (de) * | 1997-12-18 | 1999-06-24 | Witco Surfactants Gmbh | Wäßrige Weichspülmittel mit verbessertem Weichgriff |
CA2609058A1 (en) | 2005-05-18 | 2006-11-23 | Stepan Company | Low solids, high viscosity fabric softener compositions and process for making the same |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2393100A2 (fr) * | 1977-05-30 | 1978-12-29 | Procter & Gamble | Composition de traitement de textiles a base d'agent tensio-actif cationique et de lubrifiant non-ionique |
EP0240727A2 (de) * | 1986-03-12 | 1987-10-14 | Henkel Kommanditgesellschaft auf Aktien | Textilweichmacher-Konzentrat |
EP0471606A2 (de) * | 1990-08-16 | 1992-02-19 | Colgate-Palmolive Company | Stabilisiertes Hautbehandlungsmittel |
EP0490053A1 (de) * | 1990-12-07 | 1992-06-17 | Wella Aktiengesellschaft | Haarkur in Form einer Mikroemulsion |
WO1993023510A1 (en) * | 1992-05-12 | 1993-11-25 | The Procter & Gamble Company | Concentrated fabric softener compositions containing biodegradable fabric softeners |
DE4232448A1 (de) * | 1992-09-28 | 1994-03-31 | Henkel Kgaa | Verfahren zur Herstellung pulverförmiger oder granularer Detergensgemische |
-
1994
- 1994-01-14 DE DE4400927A patent/DE4400927A1/de not_active Withdrawn
-
1995
- 1995-01-05 WO PCT/EP1995/000047 patent/WO1995019416A1/de not_active Application Discontinuation
- 1995-01-05 JP JP7518816A patent/JPH09508106A/ja active Pending
- 1995-01-05 EP EP95906310A patent/EP0739409A1/de not_active Withdrawn
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2393100A2 (fr) * | 1977-05-30 | 1978-12-29 | Procter & Gamble | Composition de traitement de textiles a base d'agent tensio-actif cationique et de lubrifiant non-ionique |
EP0240727A2 (de) * | 1986-03-12 | 1987-10-14 | Henkel Kommanditgesellschaft auf Aktien | Textilweichmacher-Konzentrat |
EP0471606A2 (de) * | 1990-08-16 | 1992-02-19 | Colgate-Palmolive Company | Stabilisiertes Hautbehandlungsmittel |
EP0490053A1 (de) * | 1990-12-07 | 1992-06-17 | Wella Aktiengesellschaft | Haarkur in Form einer Mikroemulsion |
WO1993023510A1 (en) * | 1992-05-12 | 1993-11-25 | The Procter & Gamble Company | Concentrated fabric softener compositions containing biodegradable fabric softeners |
DE4232448A1 (de) * | 1992-09-28 | 1994-03-31 | Henkel Kgaa | Verfahren zur Herstellung pulverförmiger oder granularer Detergensgemische |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0754215B1 (de) * | 1994-04-07 | 2001-05-23 | Unilever Plc | Gewebeweichmacherzusammensetzung |
EP0762830B1 (de) * | 1994-06-02 | 2001-12-19 | Kao Corporation | Methode zur Wirkungssteigerung von Agrarchemikalien |
EP2576743B1 (de) | 2010-05-28 | 2015-11-11 | Colgate-Palmolive Company | Fettsäurekettensättigung bei einem esterquat auf alkanolaminbasis |
WO2018219997A1 (en) | 2017-05-30 | 2018-12-06 | Roche Diagnostics Gmbh | Catalysts for reversing formaldehyde adducts and crosslinks |
Also Published As
Publication number | Publication date |
---|---|
EP0739409A1 (de) | 1996-10-30 |
DE4400927A1 (de) | 1995-07-20 |
JPH09508106A (ja) | 1997-08-19 |
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