WO2021081969A1 - Quaternary ammonium compound mixture and fabric conditioning composition - Google Patents
Quaternary ammonium compound mixture and fabric conditioning composition Download PDFInfo
- Publication number
- WO2021081969A1 WO2021081969A1 PCT/CN2019/114944 CN2019114944W WO2021081969A1 WO 2021081969 A1 WO2021081969 A1 WO 2021081969A1 CN 2019114944 W CN2019114944 W CN 2019114944W WO 2021081969 A1 WO2021081969 A1 WO 2021081969A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- quaternary ammonium
- ammonium compound
- acid
- compound mixture
- fatty acid
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 172
- 150000003856 quaternary ammonium compounds Chemical class 0.000 title claims abstract description 119
- 230000003750 conditioning effect Effects 0.000 title claims abstract description 57
- 239000004744 fabric Substances 0.000 title claims abstract description 49
- -1 amine compound Chemical class 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 25
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 24
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 24
- 150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 23
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 17
- 239000000194 fatty acid Substances 0.000 claims abstract description 17
- 229930195729 fatty acid Natural products 0.000 claims abstract description 17
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 17
- 238000005886 esterification reaction Methods 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000005956 quaternization reaction Methods 0.000 claims description 7
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000012736 aqueous medium Substances 0.000 claims description 6
- 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 claims description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 6
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 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 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 claims description 3
- 235000021357 Behenic acid Nutrition 0.000 claims description 3
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 3
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 3
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005639 Lauric acid Substances 0.000 claims description 3
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- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- 235000021322 Vaccenic acid Nutrition 0.000 claims description 3
- UWHZIFQPPBDJPM-FPLPWBNLSA-M Vaccenic acid Natural products CCCCCC\C=C/CCCCCCCCCC([O-])=O UWHZIFQPPBDJPM-FPLPWBNLSA-M 0.000 claims description 3
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- 229940116226 behenic acid Drugs 0.000 claims description 3
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 3
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 3
- OYHQOLUKZRVURQ-AVQMFFATSA-N linoelaidic acid Chemical compound CCCCC\C=C\C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-AVQMFFATSA-N 0.000 claims description 3
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
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- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 3
- 229960003656 ricinoleic acid Drugs 0.000 claims description 3
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 3
- NNNVXFKZMRGJPM-KHPPLWFESA-N sapienic acid Chemical compound CCCCCCCCC\C=C/CCCCC(O)=O NNNVXFKZMRGJPM-KHPPLWFESA-N 0.000 claims description 3
- 239000008117 stearic acid Substances 0.000 claims description 3
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 3
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 235000019645 odor Nutrition 0.000 description 14
- 238000003860 storage Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
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- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 230000002349 favourable effect Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000008236 heating water Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 230000037331 wrinkle reduction Effects 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
- D06M13/2246—Esters of unsaturated carboxylic acids
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/372—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
Definitions
- the present disclosure generally relates to a quaternary ammonium compound mixture, and a fabric conditioning composition comprising the same.
- Quaternary ammonium compounds are widely used in fabric conditioners, which can be added in the rinse cycle of the laundering process to soften fabrics. To be effective and use friendly as fabric conditioners, the quaternary ammonium compounds need to satisfy some requirements and considerations.
- the quaternary ammonium compound mixture provided by the present disclosure doesn’t have a rancid odor, which is particularly advantageous when it is used to the downstream applications, including but not limited fabric conditioning, hair conditioning, and skin caring.
- the quaternary ammonium compound mixture provided by the present disclosure may impart better storage stability to the compositions comprising the same.
- a quaternary ammonium compound mixture prepared from a method comprising an esterification reaction step between
- a, b, m, and n each is independently selected from an integer of 0 to 10
- p is selected from an integer of 1 to 10 provided that at least one of a and b is not 0, and at least one of m and n is not 0, wherein the molar ratio of the amine compound having formula I or derivatives thereof to the fatty acid mixture is in the range of from about 1.25: 2 to 10: 2.
- a, b, m, and n each is independently selected from an integer of 0 to 3
- p is selected from an integer of 1 to 3.
- the saturated fatty acid is one or more selected from C 8 -C 22 linear or branched saturated fatty acid or derivatives thereof.
- the unsaturated fatty acid is one or more selected from C 8 -C 22 linear or branched unsaturated fatty acid or derivatives thereof.
- the molar ratio of the amine compound having formula I or derivatives thereof to the fatty acid mixture is in the range of from about 1.25: 2 to 4: 2.
- the molar ratio of the at least one saturated fatty acid to the at least one unsaturated fatty acid is in the range of from about 90: 10 to 20: 80.
- the molar ratio of the at least one saturated fatty acid to the at least one unsaturated fatty acid is in the range of from about 80: 20 to 30: 70.
- the at least one saturated fatty acid is one or more selected from a group consisting of caprylic acid, capric acid, lauric acid, myristic acid, behenic acid, palmitic acid and stearic acid.
- the at least one unsaturated fatty acid is one or more selected from a group consisting of ricinoleic acid, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linoelaidic acid, arachidonic acid, and erucic acid.
- p is an integer of 1.
- a is 1, b is 0, m is 1, n is 0.
- a is 0, b is 1, m is 0, n is 1.
- the method further comprises a quaternization step for quaternizing products of the esterification reaction step.
- the esterification reaction step is carried out at a temperature of from about 100°C to 250°C, in the presence of a catalyst.
- a quaternary ammonium compound mixture comprising a quaternary ammonium compound of formula IV and a quaternary ammonium compound of formula V,
- a, b, m, and n each is independently selected from an integer of 0 to 10
- p is selected from an integer of 1 to 10, provided that at least one of a and b is not 0, and at least one of m and n is not 0,
- R 1 and R 2 are the same or different, and are independently selected from C 7 -C 21 linear or branched alkyl groups,
- R 3 and R 4 are the same or different, and are independently selected from C 7 -C 21 linear or branched alkenyl groups,
- R 9 is selected from C 1 -C 22 linear or branched alkyl groups, or C 1 -C 22 linear or branched alkyl substituted phenyl groups or naphthyl groups, and
- X - represents an anion
- a molar ratio of the quaternary ammonium compound of formula IV to the quaternary ammonium compound of formula V is in the range of from about 90: 10 to 20: 80.
- the quaternary ammonium compound mixture further comprises a quaternary ammonium compound having formula VI,
- R 5 is selected from C 7 -C 21 linear or branched alkyl groups
- R 6 is selected from C 7 -C 21 linear or branched alkenyl groups.
- the quaternary ammonium compound mixture further comprises a quaternary ammonium compound having formula VII and/or a quaternary ammonium compound having formula VIII,
- R 7 is selected from C 7 -C 21 linear or branched alky groups
- R 8 is selected from C 7 -C 21 linear or branched alkenyl groups.
- R 1 is the same as R 2
- R 3 is the same as R 4.
- R 5 and R 7 each is independently the same as R 1 or R 2
- R 6 and R 8 each is independently the same as R 3 or R 4 .
- a is 1, b is 0, m is 1, n is 0.
- a is 0, b is 1, m is 0, n is 1.
- a fabric conditioning composition comprising the quaternary ammonium compound mixture of the present disclosure.
- the quaternary ammonium compound mixture is present in an amount of 0.5%-30%by weight based on the total weight of the fabric conditioning composition.
- a hair conditioning composition comprising the quaternary ammonium compound mixture of the present disclosure.
- a skin care composition comprising the quaternary ammonium compound mixture of the present disclosure.
- a method for conditioning a fabric comprises the step of contacting the fabric with an aqueous medium comprising the fabric conditioning composition of the present disclosure.
- a method of conditioning hair comprising the step of contacting the hair with an aqueous medium comprising the hair conditioning composition of the present disclosure.
- a method of treating skin comprising the step of applying the skin care composition to the skin.
- the term "containing one/a/an” , “including one/a/an” , “comprising one/a/an” , or “having one/a/an” should be understood as being synonymous with the term “containing at least one” , “including at least one” , “comprising at least one” or “having at least one” , unless otherwise specified.
- the terms “between” and “from ...to" should be understood as being inclusive of the limits.
- any particular upper concentration, molar ratio, weight ratio, amount or temperature can be associated with any particular lower concentration, molar ratio, weight ratio, amount or temperature, respectively.
- alkyl means a saturated hydrocarbon radical, which may be linear, branched or cyclic, such as, octyl, decyl, undecyl, lauryl, myristyl, palmityl, octadecyl, cyclooctyl and the like.
- alkenyl as a group or part of a group denotes an aliphatic hydrocarbon group which contains at least one carbon-carbon double bond and which may be linear or branched.
- the group may contain a plurality of double bonds in the normal chain and the orientation about each is independently E or Z.
- Exemplary alkenyl groups include, but are not limited to, octenyl, nonenyl, tetradecenyl, heptadecenyl, and octadecenyl.
- the group may be a terminal group or a bridging group.
- alkyl substituted phenyl group means a group comprising a benzene ring, in which at least one hydrogen atom in the benezene ring is substituted with an alkyl group.
- the substituent alkyl group may be linear or branched. Examples of the substituent alkyl group includes but is not limited to methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, pentyl and n-hexyl.
- alkyl substituted naphthyl group means a group comprising a naphthalene ring, in which at least one hydrogen atom in the naphthalene ring is substituted with an alkyl group.
- the substituent alkyl group may be linear or branched. Examples of the substituent alkyl group includes but is not limited to methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, pentyl and n-hexyl.
- quaternary ammonium compound means a compound comprising a quaternized nitrogen wherein the nitrogen atom is attached to four organic groups.
- quaternary ammonium compound mixture means a mixture comprising at least one quaternary ammonium compound.
- saturated fatty acid means a saturated aliphatic carboxylic acid, which may be linear or branched.
- unsaturated fatty acid means an unsaturated aliphatic carboxylic acid which contains at least one carbon-carbon double bond and which may be linear or branched.
- a monounsaturated fatty acid includes a single carbon-carbon double bond in the hydrocarbon chain, while a polyunsaturated fatty acid includes two or more carbon-carbon double bonds.
- fatty acid mixture means a mixture of at least one saturated fatty acid or derivatives thereof and at least one unsaturated fatty acid or derivatives thereof.
- esterification reaction means the condensation reactions between the hydroxyl groups of the alkanol amines or derivatives thereof and the carboxyl groups of the fatty acid or the derivatives thereof.
- quaternization means quaternization or protonization of the nitrogen to give a positive charge to the nitrogens of the alkanol amines.
- the quaternization may be achieved by alkylation, alkenylation or alkynylation of the tertiary nitrogen.
- fabric conditioning is the broadest sense to include any conditioning benefit (s) to textile fabrics, materials, yarns, and woven fabrics.
- One such conditioning benefit is softening fabrics.
- Other non-limiting conditioning benefits include fabric lubrication, fabric relaxation, durable press, wrinkle resistance, wrinkle reduction, ease of ironing, abrasion resistance, fabric smoothing, anti-felting, anti-pilling, crispness, appearance enhancement, appearance rejuvenation, color protection, color rejuvenation, anti-shrinkage, in-wear shape retention, fabric elasticity, fabric tensile strength, fabric tear strength, static reduction, water absorbency or repellency, stain repellency; refreshing, anti-microbial, odor resistance; perfume freshness, perfume longevity, and mixtures thereof.
- hair conditioning composition means a composition for treating the hair with agents that impart to hair at least one property chosen from combability, manageability, moisture-retentivity, luster, shine and softness.
- skin care composition refers to personal care compositions that are suitable for application to the skin to provide, for example, a cosmetic effect and/or a medical effect, such as, protection from ultraviolet rays, wrinkle minimizing, wrinkle removal, skin tanning, skin softening, skin smoothing, depilation, cleansing, etc.
- the quaternary ammonium compound mixture of the present disclosure is prepared from a method comprising an esterification reaction step between an amine compound and a fatty acid mixture of at least one saturated fatty acid and at least one unsaturated fatty acid.
- the amine compounds contemplated in the present disclosure has a formula I:
- a, b, m, and n each is independently selected from an integer of 0 to 10
- p is selected from an integer of 1 to 10, provided that at least one of a and b is not 0, and at least one of m and n is not 0.
- the amine compound of formula I may be prepared by the alkoxylation of ammonia.
- ammonia is alkoxylated with alkylene oxide compounds (ethylene oxide and/or propylene oxide) .
- Alkoxylation processes may, for instance, be carried out in the presence of acidic or alkaline catalysts or, in the case of direct amine alkoxylation, the reaction may auto-catalyze (and therefore no additional catalyst is needed) .
- Alkaline catalysts may include, for instance, hydroxides or alcoholates of sodium or potassium, including NaOH, KOH, sodium methoxide, potassium methoxide, sodium ethoxide and potassium ethoxide.
- the ethyoxy unit (-CH 2 -CH 2 -O-) and the propoxy unit (-CH 2 CH (CH 3 ) -O-) may be distributed in block or randomly distributed in each chain.
- the either ethyoxy unit or the propoxy unit can link to the nitrogen atom, the same can be applied to formula IV to VIII.
- a, b, m, and n each is independently selected from an integer of 0 to 3, p is selected from an integer of 1 to 3. In another embodiment of the present disclosure, p is 1. In still another embodiment of the present disclosure, a is 1, b is 0, m is 1, n is 0. In yet another embodiment of the present disclosure, a is 0, b is 1, m is 0, n is 1.
- amine compound has the formula II as below:
- amine compound has the formula III as below:
- the derivatives of the amine compounds as illustrated above are also contemplated in the present disclosure.
- Exemplary derivatives include, but are not limited to the inorganic or organic salts of the amine compounds.
- Examples of the inorganic or organic salts of the amine compounds include but are not limited to the hydrochlorides, sulphates, oxalates, maleates and P-benzene sulfonates of the amine compounds.
- the at least one saturated fatty acid contemplated in the present disclosure is selected from C 8 -C 22 linear or branched saturated fatty acids or derivatives thereof.
- the at least one saturated fatty acid is one or more selected from a group consisting of caprylic acid, capric acid, lauric acid, myristic acid, behenic acid, palmitic acid and stearic acid.
- the at least one unsaturated fatty acid contemplated in the present disclosure is selected from C 8 -C 22 linear or branched unsaturated fatty acids or derivatives thereof.
- the at least one unsaturated fatty acid may be monounsaturated or a polyunsaturated.
- the at least one unsaturated fatty acid is one or more selected from a group consisting of ricinoleic acid, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linoelaidic acid, arachidonic acid, and erucic acid.
- the saturated and unsaturated fatty acids or the mixtures thereof may be derived from soy bean, tallow, palm, palm kernel, rape seed, lard, or coconut oil.
- Derivatives of the saturated fatty acids and the unsaturated fatty acids are also contemplated in the present disclosure.
- Exemplary derivatives include but are not limited to the acyl chlorides or hydrides thereof.
- the molar ratio of the at least one saturated fatty acid to the at least one unsaturated fatty acid is generally in the range of from about 90: 10 to 20: 80. In another embodiment, the molar ratio of the at least one saturated fatty acid to the at least one unsaturated fatty acid is generally in the range of from about 80: 20 to 30: 70.
- the molar ratio of amine compound to fatty acid mixture is generally in the range higher than about 1.25: 2. In another embodiment, the molar ratio of amine compound to fatty acid mixture is generally in the range of from about 1: 25: 2 to 10: 2. In yet another embodiment, the molar ratio of amine compound to fatty acid mixture is generally in the range of from about 1.25: 2 to 4: 2. In still another embodiment, the molar ratio of amine compound to fatty acid mixture is generally in the range of from about 1.28: 2.
- the quaternary ammonium compound mixture of the present disclosure doesn’t have a rancid odor.
- the compositions including but not limited to fabric conditioning compositions, hair conditioning compositions, and skin care compositions, comprising such a quaternary ammonium compound mixture do not have a rancid odor as well.
- the quaternary ammonium compound mixture of the present disclosure imparts much better storage stability to the compositions compared to those prepared from triethanolamine.
- the esterification reaction of the amine compound having formula I with the fatty acid mixture is carried out at a temperature of from about 100°C to 250°C in the presence of a catalyst.
- Suitable catalysts include, but are not limited to potassium hydroxide, sulphonic acid, phosphorous acid, p-toluene sulphonic acid, methane sulphonic acid, oxalic acid, hypophosphorous acid or an acceptable Lewis.
- the quaternization step is carried out by treating the esterification reaction products with a quaternizing agent. Temperature suitable for the quaternization step is in the range from about 55°Cto 100°C.
- Suitable solvents include polar solvents such as, for example, lower alcohols, i.e., C 1 -C 6 alcohols.
- Other solvents which can be employed include, but are not limited to mono-, di-, and tri-glycerides, fatty acids, glycols and mixtures thereof.
- Suitable quaternizing agents include, but are not limited to the lower alkyl chlorides and bromides, e.g., methyl chloride; the di-lower alkyl sulfates; ethylene chlorohydrin; epichlorohydrin and benzyl chloride or iodide.
- Exemplary quaternizing agents include, but are not limited to methyl chloride, dimethyl and diethyl sulfate and benzyl chloride.
- quaternary ammonium compound mixture comprising quaternary ammonium compounds respectively having formulae IV and V:
- R 1 and R 2 are same or different and are independently selected from C 7 -C 21 alkyl groups
- R 3 and R 4 are same or different and are independently selected from C 7 -C 21 alkenyl groups
- R 9 is selected from C 1 -C 22 linear or branched alkyl groups, or C 1 -C 22 linear or branched alkyl substituted phenyl groups or naphthyl groups.
- X - represents an anion. Examples of X - include but are not limited to halogen, CH 3 SO 4 - or C 2 H 5 SO 4 - .
- R 1 is the same as R 2
- R 3 is the same as R 4 .
- the alkyl groups may be linear, branched or cyclic.
- Exemplaryalkyl groups include, but are not limited to: octyl, decyl, undecyl, lauryl, myristyl, palmityl, octadecyl.
- the alkenyl groups contain at least one carbon-carbon double bond and which may be linear or branched.
- the group may contain a plurality of double bonds in the normal chain and the orientation about each is independently E or Z.
- Exemplary alkenyl groups include, but are not limited to: octenyl, nonenyl, tetradecenyl, heptadecenyl, and octadecenyl.
- the alkenyl groups may be terminal groups or bridging groups.
- substituent alkyl group includes but is not limited to methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, pentyl and n-hexyl.
- the molar ratio of the quaternary ammonium compound of formulae IV to the quaternary ammonium compound of V is generally controlled in the range from about 90: 10 to 20: 80. In another embodiment of the present disclosure, the molar ratio of the quaternary ammonium compound of formulae IV to the quaternary ammonium compound of V is controlled in the range from about 80: 20 to 30: 70.
- the quaternary ammonium compound mixture comprising a quaternary ammonium compound having formula IV and a quaternary ammonium compound having formula V does not have a rancid odor.
- the compositions including but not limited to fabric conditioning compositions, hair conditioning compositions, and skin care compositions, comprising such a quaternary ammonium compound mixture do not have a rancid odor as well.
- the compositions comprising such a quaternary ammonium compound mixture have favourable storage stability.
- the quaternary ammonium compound mixture may further comprise a quaternary ammonium compound having formula VI:
- R 5 is selected from C 7 -C 21 alkyl groups and is same as R 1 or R 2
- R 6 is selected from C 7 -C 21 alkenyl groups and is same as R 3 or R 4 .
- the quaternary ammonium compound having formula VI does not have a rancid odor.
- the quaternary ammonium compound having formula VI imparts favourable storage stability to the compositions as well. Accordingly, the compositions, which contain a quaternary ammonium compound mixture further comprising the quaternary ammonium compound having formulae VI does not have a rancid odor. In addition, the compositions, which contain a quaternary ammonium compound mixture further comprising the quaternary ammonium compound having formulae VI have favorable storage stability.
- the quaternary ammonium compound mixture may further comprise a quaternary ammonium compound having formula VII:
- R 7 is selected from C 7 -C 21 alkyl groups and is same as R 1 or R 2 .
- the quaternary ammonium compound mixture may further comprise a quaternary ammonium compound having formula VIII:
- R 8 is selected from C 7 -C 21 alkenyl groups and is same as R 3 or R 4 .
- compositions which contain a quaternary ammonium compound mixture further comprising the quaternary ammonium compounds having formulae VII and/or VIII do not have a rancid odor.
- the quaternary ammonium compound having formula VII or VIII further improves the performance of the compositions in storage stability. Accordingly, the compositions, which contain a quaternary ammonium compound mixture further comprising the quaternary ammonium compounds having formulae VII and/or VIII have improved storage stability.
- the quaternary ammonium compounds having formulae IV-VIII may be prepared independently and are mixed to form the quaternary ammonium compound mixture of the present disclosure.
- the quaternary ammonium compound mixture comprising the quaternary ammonium compounds having formulae IV-VIII may be prepared from the method as described above in the present disclosure.
- the present disclosure further provides a fabric conditioning composition comprising the quaternary ammonium compound mixture of the present disclosure.
- the inventor of the present disclosure found that the fabric conditioning compositions comprising the quaternary ammonium compound mixture of the present disclosure do not have a rancid odor and have good storage stability.
- the quaternary ammonium compound mixture of the present disclosure is present in an amount from about 0.5%to 30%by weight based on the total weight of the composition.
- the quaternary ammonium compound mixture of the present disclosure is present in an amount of from about 0.5%to 20%by weight based on the total weight of the composition.
- the quaternary ammonium compound mixture of the present disclosure is present in an amount of from about 1%to 10%by weight based on the total weight of the composition.
- the quaternary ammonium compound mixture of the present disclosure is present in an amount of from about 3%to 8%by weight based on the total weight of the composition.
- the composition of the present disclosure may comprise at least one cationic polysaccharide. In one embodiment, the composition may comprise only one cationic polysaccharide.
- the composition may further comprise a fragrance material or a perfume.
- a) other products that enhance the softening performance of the composition such as silicones, amine oxides, anionic surfactants, such as lauryl ether sulphate or lauryl sulphate, sulphosuccinates, amphoteric surfactants, such as amphoacetate, nonionic surfactants such as polysorbate, polyglucoside derivatives, and cationic polymers such as polyquaternium, etc.;
- anionic surfactants such as lauryl ether sulphate or lauryl sulphate, sulphosuccinates
- amphoteric surfactants such as amphoacetate
- nonionic surfactants such as polysorbate, polyglucoside derivatives
- cationic polymers such as polyquaternium, etc.
- stabilising products such as salts of amines having a short chain, which are quaternised or non-quaternised, for example of triethanolamine, N-methyldiethanolamine, etc., and also non-ionic surfactants, such as ethoxylated fatty alcohols, ethoxylated fatty amines, polysorbate, and ethoxylated alkyl phenols; typically used at a level of from 0 to 15%by weight of the composition;
- products that improve viscosity control which is as example added when the composition comprises high concentrations of fabric conditioning active (such as the quaternary ammonium compound) ; for example inorganic salts, such as calcium chloride, magnesium chloride, calcium sulphate, sodium chloride, etc.; products which can be used improve the stability in concentrated compositions, such as compounds of the glycol type, such as, glycerol, polyglycerols, ethylene glycol, polyethylene glycols, dipropylene glycol, other polyglycols, etc.; and thickening agents for diluted compositions, for example, natural polymers derived from cellulose, guar, etc. or synthetic polymers, such as acrylamide based polymers (e.g. Flosoft 222 from SNF company) , hydrophobically-modified ethoxylated urethanes (e.g. Acusol 880 from Dow company) ;
- fabric conditioning active such as the quaternary ammonium compound
- inorganic salts such
- components for adjusting the pH which, for example, is from 2 to 8, such as any type of inorganic and/or organic acid, for example hydrochloric, sulphuric, phosphoric, citric acid etc.;
- agents that improve soil release such as the known polymers or copolymers based on terephthalates
- the fabric conditioning composition may be customarily prepared by melting the fabric conditioning actives and mixing them with other ingredients, and then adding the mixture to hot water, with agitation to homogenize and disperse the water-insoluble ingredients.
- the present disclosure also provides a method for conditioning a fabric.
- the method comprises the step of contacting an aqueous medium containing the composition of the present disclosure with the fabric.
- the quaternary ammonium compound mixture of the present disclosure may be utilized in a hair conditioning composition.
- the present disclosure also provides a method for conditioning hair. The method comprises the step of contacting the hair with an aqueous medium comprising the hair conditioning composition.
- the quaternary ammonium compound mixture of the present disclosure may be utilized in a skin care composition.
- the present disclosure also provides a method for treating skin. The method comprises the step of applying the skin care composition to the skin.
- RC5068 perfume purchased from Internal Flavor & Fragrance
- DM preservative purchased from Solvay
- LS dye purchased from Milliken Chemical.
- the quaternary ammonium compound mixture was prepared according to the procedure below: the fatty acid mixture and amine compound were charged to a 2000 ml 4 neck, round bottom flask. The reaction mixture was reacted under heating, and continued until an acid value of ⁇ 10 mg KOH and a base value of 77-84 mg KOH were reached.
- the quaternary ammonium compound mixture of the present disclosure does not have rancid odor.
- the fabric condition composition is prepared by the following steps:
- the storage stability is characterized by flowability which is determined by viscosity at 60rpm measured with Brookfield LVT viscometer Spindle #63.
- the odors of the fabric conditioning compositions were tested based on the olfactory sensation of the testing personnel.
- the fabric conditioning composition comprising the quaternary ammonium compound mixture of the present disclosure doesn’t have a rancid odor.
- the fabric conditioning composition comprising the quaternary ammonium compound mixture of the present disclosure has a low viscosity after storage for 12 weeks at 45°C. Therefore, the fabric conditioning composition comprising the quaternary ammonium compound mixture of the present disclosure still has good flowability after storage for 12 weeks at 45°C which indicates favorable storage stability.
- a commercial conditioner TEP-88 was used as a reference, at the same weight concentration as in the compositions according to the disclosure (namely 0.004%) .
- the fabric conditioning composition of the present disclosure has favorable conditioning performance as commercial conditioning products.
Abstract
A quaternary ammonium compound mixture prepared from a method comprising an esterification reaction step between a fatty acid mixture of at least one saturated fatty acid and at least one unsaturated fatty acid and an amine compound, and a fabric conditioning composition comprising the quaternary ammonium compound mixture.
Description
The present disclosure generally relates to a quaternary ammonium compound mixture, and a fabric conditioning composition comprising the same.
Quaternary ammonium compounds are widely used in fabric conditioners, which can be added in the rinse cycle of the laundering process to soften fabrics. To be effective and use friendly as fabric conditioners, the quaternary ammonium compounds need to satisfy some requirements and considerations.
Summary of the invention
It was surprisingly found that the quaternary ammonium compound mixture provided by the present disclosure doesn’t have a rancid odor, which is particularly advantageous when it is used to the downstream applications, including but not limited fabric conditioning, hair conditioning, and skin caring. In the meantime, the quaternary ammonium compound mixture provided by the present disclosure may impart better storage stability to the compositions comprising the same.
It should be noted that the above-stated technical effects shall not be considered exhaustive, and to a person skilled in the art, it may have other technical effects by the embodiments in the present disclosure.
In a first aspect of the present disclosure, there is provided a quaternary ammonium compound mixture prepared from a method comprising an esterification reaction step between
(a) a fatty acid mixture of at least one saturated fatty acid and at least one unsaturated fatty acid; and
(b) an amine compound having formula I or derivatives thereof
wherein a, b, m, and n each is independently selected from an integer of 0 to 10, p is selected from an integer of 1 to 10, provided that at least one of a and b is not 0, and at least one of m and n is not 0, wherein the molar ratio of the amine compound having formula I or derivatives thereof to the fatty acid mixture is in the range of from about 1.25: 2 to 10: 2.
According to the first aspect of the present disclosure, a, b, m, and n each is independently selected from an integer of 0 to 3, p is selected from an integer of 1 to 3.
According to the first aspect of the present disclosure, the saturated fatty acid is one or more selected from C
8-C
22 linear or branched saturated fatty acid or derivatives thereof.
According to the first aspect of the present disclosure, the unsaturated fatty acid is one or more selected from C
8-C
22 linear or branched unsaturated fatty acid or derivatives thereof.
According to the first aspect of the present disclosure, the molar ratio of the amine compound having formula I or derivatives thereof to the fatty acid mixture is in the range of from about 1.25: 2 to 4: 2.
According to the first aspect of the present disclosure, the molar ratio of the at least one saturated fatty acid to the at least one unsaturated fatty acid is in the range of from about 90: 10 to 20: 80.
According to the first aspect of the present disclosure, the molar ratio of the at least one saturated fatty acid to the at least one unsaturated fatty acid is in the range of from about 80: 20 to 30: 70.
According to the first aspect of the present disclosure, the at least one saturated fatty acid is one or more selected from a group consisting of caprylic acid, capric acid, lauric acid, myristic acid, behenic acid, palmitic acid and stearic acid.
According to the first aspect of the present disclosure, the at least one unsaturated fatty acid is one or more selected from a group consisting of ricinoleic acid, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linoelaidic acid, arachidonic acid, and erucic acid.
According to the first aspect of the present disclosure, p is an integer of 1.
According to the first aspect of the present disclosure, a is 1, b is 0, m is 1, n is 0.
According to the first aspect of the present disclosure, a is 0, b is 1, m is 0, n is 1.
According to the first aspect of the present disclosure, the method further comprises a quaternization step for quaternizing products of the esterification reaction step.
According to the first aspect of the present disclosure, the esterification reaction step is carried out at a temperature of from about 100℃ to 250℃, in the presence of a catalyst.
In a second aspect of the present disclosure, there is provided a quaternary ammonium compound mixture comprising a quaternary ammonium compound of formula IV and a quaternary ammonium compound of formula V,
wherein
a, b, m, and n each is independently selected from an integer of 0 to 10, p is selected from an integer of 1 to 10, provided that at least one of a and b is not 0, and at least one of m and n is not 0,
R
1 and R
2 are the same or different, and are independently selected from C
7-C
21 linear or branched alkyl groups,
R
3 and R
4 are the same or different, and are independently selected from C
7-C
21 linear or branched alkenyl groups,
R
9 is selected from C
1-C
22 linear or branched alkyl groups, or C
1-C
22 linear or branched alkyl substituted phenyl groups or naphthyl groups, and
X
-represents an anion; and
a molar ratio of the quaternary ammonium compound of formula IV to the quaternary ammonium compound of formula V is in the range of from about 90: 10 to 20: 80.
According to the second aspect of the present disclosure, the quaternary ammonium compound mixture further comprises a quaternary ammonium compound having formula VI,
wherein:
R
5 is selected from C
7-C
21 linear or branched alkyl groups; and
R
6 is selected from C
7-C
21 linear or branched alkenyl groups.
According to the second aspect of the present disclosure, the quaternary ammonium compound mixture further comprises a quaternary ammonium compound having formula VII and/or a quaternary ammonium compound having formula VIII,
wherein:
R
7 is selected from C
7-C
21 linear or branched alky groups; and
R
8 is selected from C
7-C
21 linear or branched alkenyl groups.
According to the second aspect of the present disclosure, R
1 is the same as R
2, and R
3 is the same as R
4.
According to the second aspect of the present disclosure, R
5 and R
7 each is independently the same as R
1 or R
2, and R
6 and R
8 each is independently the same as R
3 or R
4.
According to the second aspect of the present disclosure, wherein p is 1.
According to the second aspect of the present disclosure, a is 1, b is 0, m is 1, n is 0.
According to the second aspect of the present disclosure, a is 0, b is 1, m is 0, n is 1.
In a third aspect of the present disclosure, there is provided an application of the quaternary ammonium compound mixture of the present disclosure in conditioning fabric, conditioning hair or skin care.
In a fourth aspect of the present disclosure, there is provided a fabric conditioning composition comprising the quaternary ammonium compound mixture of the present disclosure.
According to the fourth aspect of the present disclosure, the quaternary ammonium compound mixture is present in an amount of 0.5%-30%by weight based on the total weight of the fabric conditioning composition.
In a fifth aspect of the present disclosure, there is provided a hair conditioning composition comprising the quaternary ammonium compound mixture of the present disclosure.
In a sixth aspect of the present disclosure, there is provided a skin care composition comprising the quaternary ammonium compound mixture of the present disclosure.
In a seventh aspect of the present disclosure, there is provided a method for conditioning a fabric. The method comprises the step of contacting the fabric with an aqueous medium comprising the fabric conditioning composition of the present disclosure.
In an eighth aspect of the present disclosure, there is provided a method of conditioning hair, comprising the step of contacting the hair with an aqueous medium comprising the hair conditioning composition of the present disclosure.
In a ninth aspect of the present disclosure, there is provided a method of treating skin, comprising the step of applying the skin care composition to the skin.
Definition
Throughout the description, including the claims, the term "containing one/a/an" , "including one/a/an" , "comprising one/a/an" , or "having one/a/an" should be understood as being synonymous with the term "containing at least one" , "including at least one" , "comprising at least one" or "having at least one" , unless otherwise specified. The terms "between" and "from …to…" should be understood as being inclusive of the limits.
The articles "a" , "an" and "the" are used to refer to one or more than one (i.e., to at least one) of the grammatical object of the article.
It should be noted that in specifying any range of concentration, molar ratio, weight ratio, amount or temperature, any particular upper concentration, molar ratio, weight ratio, amount or temperature can be associated with any particular lower concentration, molar ratio, weight ratio, amount or temperature, respectively.
As used herein, the term "alkyl" means a saturated hydrocarbon radical, which may be linear, branched or cyclic, such as, octyl, decyl, undecyl, lauryl, myristyl, palmityl, octadecyl, cyclooctyl and the like.
As used herein, the term "alkenyl" as a group or part of a group denotes an aliphatic hydrocarbon group which contains at least one carbon-carbon double bond and which may be linear or branched. The group may contain a plurality of double bonds in the normal chain and the orientation about each is independently E or Z. Exemplary alkenyl groups include, but are not limited to, octenyl, nonenyl, tetradecenyl, heptadecenyl, and octadecenyl. The group may be a terminal group or a bridging group. As used herein, the term "alkyl substituted phenyl group" means a group comprising a benzene ring, in which at least one hydrogen atom in the benezene ring is substituted with an alkyl group. The substituent alkyl group may be linear or branched. Examples of the substituent alkyl group includes but is not limited to methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, pentyl and n-hexyl.
As used herein, the term "alkyl substituted naphthyl group" means a group comprising a naphthalene ring, in which at least one hydrogen atom in the naphthalene ring is substituted with an alkyl group. The substituent alkyl group may be linear or branched. Examples of the substituent alkyl group includes but is not limited to methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, pentyl and n-hexyl.
As used herein, the terminology " (C
m-C
n) " in reference to an organic group, wherein n and m are each integers, indicates that the group may contain from m carbon atoms to n carbon atoms per group.
As used herein, the term "quaternary ammonium compound" means a compound comprising a quaternized nitrogen wherein the nitrogen atom is attached to four organic groups.
As used herein, the term "quaternary ammonium compound mixture" means a mixture comprising at least one quaternary ammonium compound.
As used herein, the term "saturated fatty acid" means a saturated aliphatic carboxylic acid, which may be linear or branched.
As used herein, the term "unsaturated fatty acid" means an unsaturated aliphatic carboxylic acid which contains at least one carbon-carbon double bond and which may be linear or branched. A monounsaturated fatty acid includes a single carbon-carbon double bond in the hydrocarbon chain, while a polyunsaturated fatty acid includes two or more carbon-carbon double bonds.
As used herein, the term "fatty acid mixture" means a mixture of at least one saturated fatty acid or derivatives thereof and at least one unsaturated fatty acid or derivatives thereof.
As used herein, the term "esterification reaction" means the condensation reactions between the hydroxyl groups of the alkanol amines or derivatives thereof and the carboxyl groups of the fatty acid or the derivatives thereof.
As used herein, the term "quaternization" means quaternization or protonization of the nitrogen to give a positive charge to the nitrogens of the alkanol amines. The quaternization may be achieved by alkylation, alkenylation or alkynylation of the tertiary nitrogen.
As used herein, the term "fabric conditioning" is the broadest sense to include any conditioning benefit (s) to textile fabrics, materials, yarns, and woven fabrics. One such conditioning benefit is softening fabrics. Other non-limiting conditioning benefits include fabric lubrication, fabric relaxation, durable press, wrinkle resistance, wrinkle reduction, ease of ironing, abrasion resistance, fabric smoothing, anti-felting, anti-pilling, crispness, appearance enhancement, appearance rejuvenation, color protection, color rejuvenation, anti-shrinkage, in-wear shape retention, fabric elasticity, fabric tensile strength, fabric tear strength, static reduction, water absorbency or repellency, stain repellency; refreshing, anti-microbial, odor resistance; perfume freshness, perfume longevity, and mixtures thereof.
As used herein, the term "hair conditioning composition" means a composition for treating the hair with agents that impart to hair at least one property chosen from combability, manageability, moisture-retentivity, luster, shine and softness.
As used herein, the term "skin care composition" refers to personal care compositions that are suitable for application to the skin to provide, for example, a cosmetic effect and/or a medical effect, such as, protection from ultraviolet rays, wrinkle minimizing, wrinkle removal, skin tanning, skin softening, skin smoothing, depilation, cleansing, etc.
Quaternary ammonium compound mixture
The quaternary ammonium compound mixture of the present disclosure is prepared from a method comprising an esterification reaction step between an amine compound and a fatty acid mixture of at least one saturated fatty acid and at least one unsaturated fatty acid.
The amine compounds contemplated in the present disclosure has a formula I:
wherein a, b, m, and n each is independently selected from an integer of 0 to 10, p is selected from an integer of 1 to 10, provided that at least one of a and b is not 0, and at least one of m and n is not 0.
The amine compound of formula I may be prepared by the alkoxylation of ammonia. In a typical procedure, ammonia is alkoxylated with alkylene oxide compounds (ethylene oxide and/or propylene oxide) . Alkoxylation processes may, for instance, be carried out in the presence of acidic or alkaline catalysts or, in the case of direct amine alkoxylation, the reaction may auto-catalyze (and therefore no additional catalyst is needed) . Alkaline catalysts may include, for instance, hydroxides or alcoholates of sodium or potassium, including NaOH, KOH, sodium methoxide, potassium methoxide, sodium ethoxide and potassium ethoxide.
In the above formula I, the ethyoxy unit (-CH
2-CH
2-O-) and the propoxy unit (-CH
2CH (CH
3) -O-) may be distributed in block or randomly distributed in each chain. Although as shown in the formula I, it is to be understood that the either ethyoxy unit or the propoxy unit can link to the nitrogen atom, the same can be applied to formula IV to VIII.
In one embodiment of the present disclosure, a, b, m, and n each is independently selected from an integer of 0 to 3, p is selected from an integer of 1 to 3. In another embodiment of the present disclosure, p is 1. In still another embodiment of the present disclosure, a is 1, b is 0, m is 1, n is 0. In yet another embodiment of the present disclosure, a is 0, b is 1, m is 0, n is 1.
In one embodiment of the present disclosure, p is 1, a is 1, b is 0, m is 1, n is 0. In this embodiment, the amine compound has the formula II as below:
In another embodiment of the present disclosure, p is 1, a is 0, b is 1, m is 0, n is 1. In this embodiment, the amine compound has the formula III as below:
The derivatives of the amine compounds as illustrated above are also contemplated in the present disclosure. Exemplary derivatives include, but are not limited to the inorganic or organic salts of the amine compounds. Examples of the inorganic or organic salts of the amine compounds include but are not limited to the hydrochlorides, sulphates, oxalates, maleates and P-benzene sulfonates of the amine compounds.
The at least one saturated fatty acid contemplated in the present disclosure is selected from C
8-C
22 linear or branched saturated fatty acids or derivatives thereof. In one embodiment, the at least one saturated fatty acid is one or more selected from a group consisting of caprylic acid, capric acid, lauric acid, myristic acid, behenic acid, palmitic acid and stearic acid.
The at least one unsaturated fatty acid contemplated in the present disclosure is selected from C
8-C
22 linear or branched unsaturated fatty acids or derivatives thereof. The at least one unsaturated fatty acid may be monounsaturated or a polyunsaturated. In one embodiment, the at least one unsaturated fatty acid is one or more selected from a group consisting of ricinoleic acid, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linoelaidic acid, arachidonic acid, and erucic acid.
The saturated and unsaturated fatty acids or the mixtures thereof may be derived from soy bean, tallow, palm, palm kernel, rape seed, lard, or coconut oil. Derivatives of the saturated fatty acids and the unsaturated fatty acids are also contemplated in the present disclosure. Exemplary derivatives include but are not limited to the acyl chlorides or hydrides thereof.
In one embodiment of the present disclosure, the molar ratio of the at least one saturated fatty acid to the at least one unsaturated fatty acid is generally in the range of from about 90: 10 to 20: 80. In another embodiment, the molar ratio of the at least one saturated fatty acid to the at least one unsaturated fatty acid is generally in the range of from about 80: 20 to 30: 70.
In one embodiment of the present disclosure, the molar ratio of amine compound to fatty acid mixture is generally in the range higher than about 1.25: 2. In another embodiment, the molar ratio of amine compound to fatty acid mixture is generally in the range of from about 1: 25: 2 to 10: 2. In yet another embodiment, the molar ratio of amine compound to fatty acid mixture is generally in the range of from about 1.25: 2 to 4: 2. In still another embodiment, the molar ratio of amine compound to fatty acid mixture is generally in the range of from about 1.28: 2.
The quaternary ammonium compound mixture of the present disclosure doesn’t have a rancid odor. The compositions, including but not limited to fabric conditioning compositions, hair conditioning compositions, and skin care compositions, comprising such a quaternary ammonium compound mixture do not have a rancid odor as well. In addition, the quaternary ammonium compound mixture of the present disclosure imparts much better storage stability to the compositions compared to those prepared from triethanolamine.
The esterification reaction of the amine compound having formula I with the fatty acid mixture is carried out at a temperature of from about 100℃ to 250℃ in the presence of a catalyst. Suitable catalysts include, but are not limited to potassium hydroxide, sulphonic acid, phosphorous acid, p-toluene sulphonic acid, methane sulphonic acid, oxalic acid, hypophosphorous acid or an acceptable Lewis.
After the esterification reaction, the quaternization step is carried out by treating the esterification reaction products with a quaternizing agent. Temperature suitable for the quaternization step is in the range from about 55℃to 100℃. Suitable solvents include polar solvents such as, for example, lower alcohols, i.e., C
1-C
6 alcohols. Other solvents which can be employed include, but are not limited to mono-, di-, and tri-glycerides, fatty acids, glycols and mixtures thereof. Suitable quaternizing agents include, but are not limited to the lower alkyl chlorides and bromides, e.g., methyl chloride; the di-lower alkyl sulfates; ethylene chlorohydrin; epichlorohydrin and benzyl chloride or iodide. Exemplary quaternizing agents include, but are not limited to methyl chloride, dimethyl and diethyl sulfate and benzyl chloride.
In another aspect of the present disclosure, there is provided a quaternary ammonium compound mixture comprising quaternary ammonium compounds respectively having formulae IV and V:
wherein a, b, p, m, n are as defined above. R
1 and R
2 are same or different and are independently selected from C
7-C
21 alkyl groups, R
3 and R
4 are same or different and are independently selected from C
7-C
21 alkenyl groups, R
9 is selected from C
1-C
22 linear or branched alkyl groups, or C
1-C
22 linear or branched alkyl substituted phenyl groups or naphthyl groups. X
-represents an anion. Examples of X
-include but are not limited to halogen, CH
3 SO
4
-or C
2 H
5 SO
4
-. In one embodiment of the present disclosure, R
1 is the same as R
2, and R
3 is the same as R
4.
The alkyl groups may be linear, branched or cyclic. Exemplaryalkyl groups include, but are not limited to: octyl, decyl, undecyl, lauryl, myristyl, palmityl, octadecyl.
The alkenyl groups contain at least one carbon-carbon double bond and which may be linear or branched. The group may contain a plurality of double bonds in the normal chain and the orientation about each is independently E or Z. Exemplary alkenyl groups include, but are not limited to: octenyl, nonenyl, tetradecenyl, heptadecenyl, and octadecenyl. The alkenyl groups may be terminal groups or bridging groups.
Examples of the substituent alkyl group includes but is not limited to methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, pentyl and n-hexyl.
In one embodiment of the present disclosure, the molar ratio of the quaternary ammonium compound of formulae IV to the quaternary ammonium compound of V is generally controlled in the range from about 90: 10 to 20: 80. In another embodiment of the present disclosure, the molar ratio of the quaternary ammonium compound of formulae IV to the quaternary ammonium compound of V is controlled in the range from about 80: 20 to 30: 70.
The quaternary ammonium compound mixture comprising a quaternary ammonium compound having formula IV and a quaternary ammonium compound having formula V does not have a rancid odor. The compositions, including but not limited to fabric conditioning compositions, hair conditioning compositions, and skin care compositions, comprising such a quaternary ammonium compound mixture do not have a rancid odor as well. In addition, the compositions comprising such a quaternary ammonium compound mixture have favourable storage stability.
In one embodiment of the present disclosure, the quaternary ammonium compound mixture may further comprise a quaternary ammonium compound having formula VI:
wherein a, b, p, m, n, R
9 and X
-are as defined above. R
5 is selected from C
7-C
21 alkyl groups and is same as R
1 or R
2, R
6 is selected from C
7-C
21 alkenyl groups and is same as R
3 or R
4.
The quaternary ammonium compound having formula VI does not have a rancid odor. The quaternary ammonium compound having formula VI imparts favourable storage stability to the compositions as well. Accordingly, the compositions, which contain a quaternary ammonium compound mixture further comprising the quaternary ammonium compound having formulae VI does not have a rancid odor. In addition, the compositions, which contain a quaternary ammonium compound mixture further comprising the quaternary ammonium compound having formulae VI have favorable storage stability.
In another embodiment of the present disclosure, the quaternary ammonium compound mixture may further comprise a quaternary ammonium compound having formula VII:
herein a, b, p, m, n, R
9 and X
-are as defined above. R
7 is selected from C
7-C
21 alkyl groups and is same as R
1 or R
2.
In still another embodiment of the present disclosure, the quaternary ammonium compound mixture may further comprise a quaternary ammonium compound having formula VIII:
wherein a, b, p, m, n, R
9 and X
-are as defined above. R
8 is selected from C
7-C
21 alkenyl groups and is same as R
3 or R
4.
The compositions, which contain a quaternary ammonium compound mixture further comprising the quaternary ammonium compounds having formulae VII and/or VIII do not have a rancid odor. In addition, the quaternary ammonium compound having formula VII or VIII further improves the performance of the compositions in storage stability. Accordingly, the compositions, which contain a quaternary ammonium compound mixture further comprising the quaternary ammonium compounds having formulae VII and/or VIII have improved storage stability.
In one embodiment of the present disclosure, the quaternary ammonium compounds having formulae IV-VIII may be prepared independently and are mixed to form the quaternary ammonium compound mixture of the present disclosure. In another embodiment of the present disclosure, the quaternary ammonium compound mixture comprising the quaternary ammonium compounds having formulae IV-VIII may be prepared from the method as described above in the present disclosure.
Fabric conditioning composition
The present disclosure further provides a fabric conditioning composition comprising the quaternary ammonium compound mixture of the present disclosure.
The inventor of the present disclosure found that the fabric conditioning compositions comprising the quaternary ammonium compound mixture of the present disclosure do not have a rancid odor and have good storage stability. In one embodiment, the quaternary ammonium compound mixture of the present disclosure is present in an amount from about 0.5%to 30%by weight based on the total weight of the composition. In another embodiment, the quaternary ammonium compound mixture of the present disclosure is present in an amount of from about 0.5%to 20%by weight based on the total weight of the composition. In yet another embodiment, the quaternary ammonium compound mixture of the present disclosure is present in an amount of from about 1%to 10%by weight based on the total weight of the composition. In still yet another embodiment, the quaternary ammonium compound mixture of the present disclosure is present in an amount of from about 3%to 8%by weight based on the total weight of the composition.
In one embodiment, the composition of the present disclosure may comprise at least one cationic polysaccharide. In one embodiment, the composition may comprise only one cationic polysaccharide.
In one embodiment, the composition may further comprise a fragrance material or a perfume.
In referring to optional ingredients, without this having to be regarded as an exhaustive description of all possibilities, which, on the other hand, are well known to the person skilled in the art, the following may be mentioned:
a) other products that enhance the softening performance of the composition, such as silicones, amine oxides, anionic surfactants, such as lauryl ether sulphate or lauryl sulphate, sulphosuccinates, amphoteric surfactants, such as amphoacetate, nonionic surfactants such as polysorbate, polyglucoside derivatives, and cationic polymers such as polyquaternium, etc.;
b) stabilising products, such as salts of amines having a short chain, which are quaternised or non-quaternised, for example of triethanolamine, N-methyldiethanolamine, etc., and also non-ionic surfactants, such as ethoxylated fatty alcohols, ethoxylated fatty amines, polysorbate, and ethoxylated alkyl phenols; typically used at a level of from 0 to 15%by weight of the composition;
c) products that improve viscosity control, which is as example added when the composition comprises high concentrations of fabric conditioning active (such as the quaternary ammonium compound) ; for example inorganic salts, such as calcium chloride, magnesium chloride, calcium sulphate, sodium chloride, etc.; products which can be used improve the stability in concentrated compositions, such as compounds of the glycol type, such as, glycerol, polyglycerols, ethylene glycol, polyethylene glycols, dipropylene glycol, other polyglycols, etc.; and thickening agents for diluted compositions, for example, natural polymers derived from cellulose, guar, etc. or synthetic polymers, such as acrylamide based polymers (e.g. Flosoft 222 from SNF company) , hydrophobically-modified ethoxylated urethanes (e.g. Acusol 880 from Dow company) ;
d) components for adjusting the pH, which, for example, is from 2 to 8, such as any type of inorganic and/or organic acid, for example hydrochloric, sulphuric, phosphoric, citric acid etc.;
e) agents that improve soil release, such as the known polymers or copolymers based on terephthalates
f) bactericidal preservative agents;
g) other products such as antioxidants, colouring agents, perfumes, germicides, fungicides, anti-corrosive agents, anti-crease agents, opacifiers, optical brighteners, pearl lustre agents, etc..
The fabric conditioning composition may be customarily prepared by melting the fabric conditioning actives and mixing them with other ingredients, and then adding the mixture to hot water, with agitation to homogenize and disperse the water-insoluble ingredients.
In another embodiment, the present disclosure also provides a method for conditioning a fabric. The method comprises the step of contacting an aqueous medium containing the composition of the present disclosure with the fabric.
In still another embodiment, the quaternary ammonium compound mixture of the present disclosure may be utilized in a hair conditioning composition. The present disclosure also provides a method for conditioning hair. The method comprises the step of contacting the hair with an aqueous medium comprising the hair conditioning composition.
In yet another embodiment, the quaternary ammonium compound mixture of the present disclosure may be utilized in a skin care composition. The present disclosure also provides a method for treating skin. The method comprises the step of applying the skin care composition to the skin.
The following examples are included to illustrate embodiments of the quaternary ammonium compound mixture and the fabric conditioning compositions of the disclosure. Needless to say, the disclosure is not limited to the described examples.
Examples
1. materials
RC5068: perfume purchased from Internal Flavor & Fragrance;
2. Example 1-preparation of the quaternary ammonium compound mixture
The quaternary ammonium compound mixture was prepared according to the procedure below: the fatty acid mixture and amine compound were charged to a 2000 ml 4 neck, round bottom flask. The reaction mixture was reacted under heating, and continued until an acid value of<10 mg KOH and a base value of 77-84 mg KOH were reached.
The products of the above reaction were charged to a 2000 ml 4 neck, round bottom flask, and heated until molten, ethanol was added as a solvent. Dimethyl sulfate were added. The solution was allowed to be stirred and heated, until an amine value<5 mg KOH was reached.
Table 1: the quaternary ammonium compound mixture
The odors of the quaternary ammonium compound mixtures were tested based on the olfactory sensation of the testing personnel.
As illustrated in Table 1, the quaternary ammonium compound mixture of the present disclosure does not have rancid odor.
3. the fabric conditioning composition
The fabric condition composition is prepared by the following steps:
1. Melting out quaternary ammonium compounds by heating under 60℃in a vessel;
2. Heating water to 50℃ with stirring;
3. Adding melted quaternary ammonium compounds to the water;
4. Adding CaCl
2;
5. Mixing to homogeneous at 50℃;
6. Cooling down to 30℃;
7. Adding perfume and mixing for 5min;
8. Adding preservative and mixing for 5min;
9. Adding dye and mixing for 5min;
10. Adjusting pH with HCl;
11. Discharging to provide the fabric conditioning composition.
Table 2 performance in storage stability
The storage stability is characterized by flowability which is determined by viscosity at 60rpm measured with Brookfield LVT viscometer Spindle #63.
The odors of the fabric conditioning compositions were tested based on the olfactory sensation of the testing personnel.
As illustrated in Table 2, compared to the comparative example 7, the fabric conditioning composition comprising the quaternary ammonium compound mixture of the present disclosure doesn’t have a rancid odor. In addition, compared to the comparative example 1, the fabric conditioning composition comprising the quaternary ammonium compound mixture of the present disclosure has a low viscosity after storage for 12 weeks at 45℃. Therefore, the fabric conditioning composition comprising the quaternary ammonium compound mixture of the present disclosure still has good flowability after storage for 12 weeks at 45℃ which indicates favorable storage stability.
4. fabric conditioning performance
The conditioning performance was determined according to the procedure below: For the softening performance test, 2 grams of each of the composition samples were diluted in 1 liter water. Then towels were immersed into the water containing different samples (5 towels for each sample) , respectively, for 10 mins. Then, the treated towels were drawn out, span for 5 mins and dried overnight. Then, the softness of each treated towel was evaluated by five panellists independently in which the panelist touched the treated towel and felt the softness of the treated towel (double-blinded test) . The softness of the treated towels was rated in a scale of 1 to 5, wherein 1 represents the lowest softness and 5 represents the highest softness. Subsequently, the average softness rating of the towels treated by the same sample (n=25) was calculated and listed as below.
A commercial conditioner
TEP-88was used as a reference, at the same weight concentration as in the compositions according to the disclosure (namely 0.004%) .
Table 3: fabric conditioning performance
As illustrated in Table 3, the fabric conditioning composition of the present disclosure has favorable conditioning performance as commercial conditioning products.
Claims (30)
- A quaternary ammonium compound mixture prepared from a method comprising an esterification reaction step betweena) a fatty acid mixture of at least one saturated fatty acid and at least one unsaturated fatty acid; andb) an amine compound having formula I or derivatives thereof
whereina, b, m, and n each is independently selected from an integer of 0 to 10, p is selected from an integer of 1 to 10, provided that at least one of a and b is not 0, and at least one of m and n is not 0; andthe molar ratio of the amine compound having formula I or derivatives thereof to the fatty acid mixture is in the range of from about 1.25: 2 to 10: 2. - The quaternary ammonium compound mixture of claim 1, wherein a, b, m, and n each is independently selected from an integer of 0 to 3, p is selected from an integer of 1 to 3.
- The quaternary ammonium compound mixture of claim 1 or 2, wherein the saturated fatty acid is one or more selected from C 8-C 22 linear or branched saturated fatty acid or derivatives thereof.
- The quaternary ammonium compound mixture of any one of claims 1 to 3, wherein the unsaturated fatty acid is one or more selected from C 8-C 22linear or branched unsaturated fatty acid or derivatives thereof.
- The quaternary ammonium compound mixture of any one of claims 1 to 4, wherein the molar ratio of the amine compound having formula I or derivatives thereof to the fatty acid mixture is in the range of from about 1.25: 2 to 4: 2.
- The quaternary ammonium compound mixture of any one of claims 1 to 5, wherein the molar ratio of the at least one saturated fatty acid to the at least one unsaturated fatty acid is in the range of from about 90: 10 to 20: 80.
- The quaternary ammonium compound mixture of claim 6, the molar ratio of the at least one saturated fatty acid to the at least one unsaturated fatty acid is in the range of from about 80: 20 to 30: 70.
- The quaternary ammonium compound mixture of any one of claims 1 to 7, wherein the saturated fatty acid is one or more selected from the group consisting of caprylic acid, capric acid, lauric acid, myristic acid, behenic acid, palmitic acid and stearic acid.
- The quaternary ammonium compound mixture of any one of claims 1 to 8, wherein the unsaturated fatty acid is one or more selected from the group consisting of ricinoleic acid, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linoelaidic acid, arachidonic acid, and erucic acid.
- The quaternary ammonium compound mixture of any one of claims 1 to 9, wherein p is an integer of 1.
- The quaternary ammonium compound mixture of any one of claims 1 to 10, wherein a is 1, b is 0, m is 1, n is 0.
- The quaternary ammonium compound mixture of any one of claims 1 to 10, wherein a is 0, b is 1, m is 0, n is 1.
- The quaternary ammonium compound mixture of any one of claims 1 to 12, wherein the method further comprises a quaternization step for quaternizing products of the esterification reaction step.
- The quaternary ammonium compound mixture of any one of claims 1 to 13, wherein the esterification reaction step is carried out at a temperature of from about 100℃ to 250℃, in the presence of a catalyst.
- A quaternary ammonium compound mixture comprising a quaternary ammonium compound of formula IV and a quaternary ammonium compound of formula V,
whereina, b, m, and n each is independently selected from an integer of 0 to 10, p is selected from an integer of 1 to 10, provided that at least one of a and b is not 0, and at least one of m and n is not 0,R 1 and R 2 are the same or different, and are independently selected from C 7-C 21 linear or branched alkyl groups,R 3 and R 4 are the same or different, and are independently selected from C 7-C 21 linear or branched alkenyl groups,R 9 is selected from C 1-C 22 linear or branched alkyl groups, or C 1-C 22 linear or branched alkyl substituted phenyl groups or naphthyl groups, andX -represents an anion; anda molar ratio of the quaternary ammonium compound of formula IV to the quaternary ammonium compound of formula V is in the range of from about 90: 10 to 20: 80. - The quaternary ammonium compound mixture of claim 15 further comprising a quaternary ammonium compound having formula VI,
wherein:R 5 is selected from C 7-C 21 linear or branched alkyl groups; andR 6is selected from C 7-C 21 linear or branched alkenyl groups. - The quaternary ammonium compound mixture of claims 15 or 16, further comprising a quaternary ammonium compound having formula VII and/or a quaternary ammonium compound having formula VIII,
wherein:R 7is selected from C 7-C 21 linear or branched alky groups; andR 8 is selected from C 7-C 21 linear or branched alkenyl groups. - The quaternary ammonium compound mixture of any one of claims 15 to 17, wherein R 1 is the same as R 2, and R 3 is the same as R 4.
- The quaternary ammonium compound mixture of claim 17 or 18, wherein R 5 and R 7 each is independently the same as R 1 or R 2, and R 6 and R 8 each is independently the same as R 3 or R 4.
- The quaternary ammonium compound mixture of any one of claims 15 to 19, wherein p is 1.
- The quaternary ammonium compound mixture of any one of claims 15 to 20, wherein a is 1, b is 0, m is 1, n is 0.
- The quaternary ammonium compound mixture of any one of claims 15 to 20, wherein a is 0, b is 1, m is 0, n is 1.
- An application of the quaternary ammonium compound mixture according to any one of claims 1 to 22 in conditioning fabric, conditioning hair or skin care.
- A fabric conditioning composition comprising the quaternary ammonium compound mixture according to any one of claims 1 to 22.
- The fabric conditioning composition of claim 24, wherein the quaternary ammonium compound mixture is present in an amount of 0.5%-30%by weight based on the total weight of the fabric conditioning composition.
- A hair conditioning composition comprising the quaternary ammonium compound mixture according to any one of claims 1 to 22.
- A skin care composition comprising the quaternary ammonium compound mixture according to any one of claims 1 to 22.
- A method for conditioning a fabric, comprising the step of contacting the fabric with an aqueous medium comprising the fabric conditioning composition according to claim 24 or 25.
- A method of conditioning hair, comprising the step of contacting the hair with an aqueous medium comprising the hair conditioning composition according to claim 26.
- A method of treating skin, comprising the step of applying the skin care composition according to claim 27 to the skin.
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| PCT/CN2019/114944 WO2021081969A1 (en) | 2019-11-01 | 2019-11-01 | Quaternary ammonium compound mixture and fabric conditioning composition |
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| PCT/CN2019/114944 WO2021081969A1 (en) | 2019-11-01 | 2019-11-01 | Quaternary ammonium compound mixture and fabric conditioning composition |
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|---|---|---|---|---|
| EP0869114A1 (en) * | 1997-04-04 | 1998-10-07 | Dow Europe S.A. | Composition useful for softening applications and processes for the preparation thereof |
| US5961966A (en) * | 1996-12-09 | 1999-10-05 | Croda, Inc. | Quaternary fatty diesters of hydroxypropyl diethanol amine |
| WO2000006678A1 (en) * | 1998-07-30 | 2000-02-10 | The Dow Chemical Company | Composition useful for softening, cleaning, and personal care applications |
| US6559117B1 (en) * | 1993-12-13 | 2003-05-06 | The Procter & Gamble Company | Viscosity stable concentrated liquid fabric softener compositions |
| CN1419006A (en) * | 1996-05-03 | 2003-05-21 | 阿克佐诺贝尔公司 | Preparation of high content (alkyl fatty ester) dihyamine compound from trihydroxy ethylamine |
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2019
- 2019-11-01 WO PCT/CN2019/114944 patent/WO2021081969A1/en active Application Filing
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6559117B1 (en) * | 1993-12-13 | 2003-05-06 | The Procter & Gamble Company | Viscosity stable concentrated liquid fabric softener compositions |
| CN1419006A (en) * | 1996-05-03 | 2003-05-21 | 阿克佐诺贝尔公司 | Preparation of high content (alkyl fatty ester) dihyamine compound from trihydroxy ethylamine |
| US5961966A (en) * | 1996-12-09 | 1999-10-05 | Croda, Inc. | Quaternary fatty diesters of hydroxypropyl diethanol amine |
| EP0869114A1 (en) * | 1997-04-04 | 1998-10-07 | Dow Europe S.A. | Composition useful for softening applications and processes for the preparation thereof |
| WO2000006678A1 (en) * | 1998-07-30 | 2000-02-10 | The Dow Chemical Company | Composition useful for softening, cleaning, and personal care applications |
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