EP3234087A1 - Transparente textilpflegemittel - Google Patents
Transparente textilpflegemittelInfo
- Publication number
- EP3234087A1 EP3234087A1 EP15808384.0A EP15808384A EP3234087A1 EP 3234087 A1 EP3234087 A1 EP 3234087A1 EP 15808384 A EP15808384 A EP 15808384A EP 3234087 A1 EP3234087 A1 EP 3234087A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- formula
- group
- carbon atoms
- nonionic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 98
- 239000004744 fabric Substances 0.000 title abstract description 15
- -1 aminosiloxane Chemical class 0.000 claims abstract description 67
- 239000002562 thickening agent Substances 0.000 claims abstract description 21
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 125000002091 cationic group Chemical group 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 239000003795 chemical substances by application Substances 0.000 claims description 40
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 40
- 239000000194 fatty acid Substances 0.000 claims description 40
- 229930195729 fatty acid Natural products 0.000 claims description 40
- 150000004665 fatty acids Chemical class 0.000 claims description 37
- 239000000047 product Substances 0.000 claims description 34
- 239000003995 emulsifying agent Substances 0.000 claims description 30
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000004753 textile Substances 0.000 claims description 19
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 16
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 15
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 12
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 12
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 12
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 10
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 10
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 9
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 9
- 239000005639 Lauric acid Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 235000011187 glycerol Nutrition 0.000 claims description 8
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 8
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 8
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 7
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 7
- 239000005642 Oleic acid Substances 0.000 claims description 7
- 235000021314 Palmitic acid Nutrition 0.000 claims description 7
- 235000021355 Stearic acid Nutrition 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000003752 hydrotrope Substances 0.000 claims description 7
- 229920000609 methyl cellulose Polymers 0.000 claims description 7
- 239000001923 methylcellulose Substances 0.000 claims description 7
- 235000010981 methylcellulose Nutrition 0.000 claims description 7
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 7
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 7
- 239000008117 stearic acid Substances 0.000 claims description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 6
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 claims description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 6
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 6
- 244000060011 Cocos nucifera Species 0.000 claims description 6
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 6
- 125000004386 diacrylate group Chemical group 0.000 claims description 6
- 150000002334 glycols Chemical class 0.000 claims description 6
- 229960004488 linolenic acid Drugs 0.000 claims description 6
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229960002446 octanoic acid Drugs 0.000 claims description 6
- 229920000151 polyglycol Polymers 0.000 claims description 6
- 239000010695 polyglycol Substances 0.000 claims description 6
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 6
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 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 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 5
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 5
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 150000001767 cationic compounds Chemical class 0.000 claims description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 5
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 5
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 5
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 5
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 5
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 4
- 239000012875 nonionic emulsifier Substances 0.000 claims description 4
- 235000021313 oleic acid Nutrition 0.000 claims description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims description 4
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 claims description 4
- 239000003760 tallow Substances 0.000 claims description 4
- 229940061629 trideceth-9 Drugs 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 3
- LVKKFNORSNCNPP-UHFFFAOYSA-N 2,2-bis(prop-2-enoylamino)acetic acid Chemical compound C=CC(=O)NC(C(=O)O)NC(=O)C=C LVKKFNORSNCNPP-UHFFFAOYSA-N 0.000 claims description 3
- KUIYXYIWGVFQPD-UHFFFAOYSA-N 2-octyldodecanoic acid Chemical compound CCCCCCCCCCC(C(O)=O)CCCCCCCC KUIYXYIWGVFQPD-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- 229920003118 cationic copolymer Polymers 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- CNPHCSFIDKZQAK-UHFFFAOYSA-N n-prop-2-enylprop-2-enamide Chemical compound C=CCNC(=O)C=C CNPHCSFIDKZQAK-UHFFFAOYSA-N 0.000 claims description 3
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 3
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- CVLHGLWXLDOELD-UHFFFAOYSA-N 4-(Propan-2-yl)benzenesulfonic acid Chemical compound CC(C)C1=CC=C(S(O)(=O)=O)C=C1 CVLHGLWXLDOELD-UHFFFAOYSA-N 0.000 claims description 2
- 235000019482 Palm oil Nutrition 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 claims description 2
- 239000002540 palm oil Substances 0.000 claims description 2
- 244000007835 Cyamopsis tetragonoloba Species 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 19
- 230000003287 optical effect Effects 0.000 abstract description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 27
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 15
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- 239000003921 oil Substances 0.000 description 15
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- 235000002639 sodium chloride Nutrition 0.000 description 15
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- 229920000642 polymer Polymers 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 8
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- 239000001257 hydrogen Substances 0.000 description 8
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- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 3
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- 239000003513 alkali Substances 0.000 description 3
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- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 1
- QMHNQZGXPNCMCO-UHFFFAOYSA-N n,n-dimethylhexan-1-amine Chemical compound CCCCCCN(C)C QMHNQZGXPNCMCO-UHFFFAOYSA-N 0.000 description 1
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 description 1
- SFBHPFQSSDCYSL-UHFFFAOYSA-N n,n-dimethyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)C SFBHPFQSSDCYSL-UHFFFAOYSA-N 0.000 description 1
- FFDYDKFAQVYKSM-UHFFFAOYSA-N n-ethyl-n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)CC FFDYDKFAQVYKSM-UHFFFAOYSA-N 0.000 description 1
- OMEMQVZNTDHENJ-UHFFFAOYSA-N n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCNC OMEMQVZNTDHENJ-UHFFFAOYSA-N 0.000 description 1
- XJINZNWPEQMMBV-UHFFFAOYSA-N n-methylhexan-1-amine Chemical compound CCCCCCNC XJINZNWPEQMMBV-UHFFFAOYSA-N 0.000 description 1
- LYFMJSSIPHXUEN-UHFFFAOYSA-N n-methylicosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCNC LYFMJSSIPHXUEN-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002553 poly(2-methacrylolyloxyethyltrimethylammonium chloride) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000010670 sage oil Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- HFTAFOQKODTIJY-UHFFFAOYSA-N umbelliferone Natural products Cc1cc2C=CC(=O)Oc2cc1OCC=CC(C)(C)O HFTAFOQKODTIJY-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- 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
- C11D1/38—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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
-
- 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
-
- 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
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
-
- 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
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
- C11D3/3742—Nitrogen containing silicones
-
- 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
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
- C11D3/3773—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines in liquid compositions
-
- 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
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- 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
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/12—Soft surfaces, e.g. textile
Definitions
- the present invention relates to fabric care and fabric conditioning formulations of clear, transparent appearance and viscous consistency, as well as the use of these fabric conditioners and fabric conditioning formulations.
- Esterquats which are generally understood to mean the quaternized fatty acid triethanolamine ester salts, are well suited to both fiber and hair care and, in recent years, have been afforded by conventional quaternary ammonium compounds, such as, for example, improved ecotoxicological compatibility. the known
- Distearyldimethylammonium chloride displaced to a good extent from the market.
- esterquats have very good performance properties as well as a satisfactory biodegradability and a good skin-cosmetic
- the present invention solves the problem of providing transparent, viscous compositions comprising esterquats which at least partially overcome the above-described disadvantages of known formulations.
- the invention is based on the surprising finding of the inventors that the combination of special ester quats and cationic thickeners with aminosiloxanes provides an optically clear, viscous softening formulation with reduced concentra- tion of softening substances compared to comparable market formulations which have a long shelf life (no exudation) , no unpleasant odor).
- the present invention relates to a liquid, clear, homogeneous textile treatment agent, especially a fabric conditioning formulation
- X is a saturated or unsaturated hydrocarbon radical having 1 to 8
- R is a saturated or unsaturated hydrocarbon radical having 5 to 21 carbon atoms
- R 2 , R 3 and R 4 independently of one another represent a C 2 - to C 6 -hydroxyalkyl group, in particular 2-hydroxyethyl,
- Reaction product contained amino group
- Another aspect of the present invention relates to use
- X is a saturated or unsaturated hydrocarbon radical having 1 to 8 carbon atoms, and at least one monocarboxylic acid of the formula (II)
- R is a saturated or unsaturated hydrocarbon radical having 5 to 21 carbon atoms, with ii) at least one tertiary amine of the formula (III)
- R 2 , R 3 and R 4 independently of one another represent a C 2 - to C 6 -hydroxyalkyl group, in particular 2-hydroxyethyl,
- Reaction product contained amino group
- At least one aminosiloxane at least one aminosiloxane selected from the group consisting of amodimethicone / morpholinomethyl silsesquioxane copolymer, trideceth-9 PG-amodimethicone, with methylsilsesquioxane hydroxy-bound
- Numeric ranges specified in the format "from x to y" include the above values. If multiple preferred numeric ranges are specified in this format, it is understood that all ranges resulting from the combination of the various endpoints, Furthermore, amounts referring to at least one ingredient always represent the total amount of that kind of ingredient contained in the composition, unless explicitly stated otherwise Relating to "at least one emulsifier", to the total amount of emulsifiers contained in the detergent.
- alkaline earth metals are referred to below as counterions for monovalent anions, this means that the alkaline earth metal is present only in half - as sufficient to charge balance - amount of substance as the anion.
- Substances which also serve as ingredients of cosmetic products are referred to below, where appropriate, according to the International Nomenclature Cosmetic Ingredient (INCI) nomenclature. Chemical compounds carry an INCI name in English, plant ingredients are listed only after Linne in Latin, so-called trivial names such as "water”, “honey” or “sea salt” are also given in Latin.
- the INCI names can be found in the International Cosmetic Ingredient Dictionary and Handbook - Seventh Edition (1997), published by The Cosmetic, Toiletry and Fragrance Association (CTFA), 1 101 17th Street, NW, Suite 300, Washington, DC 20036, USA, and contains more than 9,000 INCI names, as well as references to more than 37,000 trade names and technical names, including its distributors from over 31 countries.
- the International Cosmetic Ingredient Dictionary and Handbook assigns to the ingredients one or more chemical classes, such as polymer ethers, and one or more functions, such as surfactants-cleansing agents, which are further explained and discussed below possibly also referred to.
- the indication CAS means that the following sequence of numbers is a name of the Chemical Abstracts Service.
- At least one refers to 1 or more, for example, 2, 3, 4, 5, 6, 7, 8, 9 or more In the context of components of those described herein
- At least one emulsifier means one or more different emulsifiers, ie, one or more different types of emulsifiers the
- Liquid as used herein includes all flowable compositions at standard conditions (20 ° C, 1013 mbar), including appropriate pastes and gels.
- Nephelometric Turbidity Unit NTU is a liquid turbidity measurement unit used in water treatment and is the unit of turbidity of a liquid measured at 90 ° angle with a calibrated nephelometer and a wavelength of measuring radiation in the infrared range at 860 nm (ISO 7027) ).
- Homogeneous refers to the agents being monophasic, liquid agents, ie those which are clear as defined above and in which no
- Phase separation of two or more liquid phases is observed.
- the pH refers to the pH determined at 25 ° C, unless otherwise stated.
- X is preferably ethane-1,2-diyl, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, hexane-1,4-diyl or cyclohexane-1, 4- diyl, more preferably for butane-1, 4-diyl.
- suitable dicarboxylic acid include, without limitation,
- Succinic acid maleic acid, glutaric acid, and especially adipic acid. Furthermore, it is also possible to use mixtures of the abovementioned acids.
- R CO is preferably an aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds. Typical examples include, but are not limited to,
- Caproic acid caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid,
- Elaidic acid petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid, and their technical mixtures, e.g. in the pressure splitting of natural fats and oils, in the reduction of aldehydes from the Roelen oxo synthesis or the dimerization of unsaturated fatty acids.
- stearic acid Preference is given to stearic acid, isostearic acid, palmitic acid, myristic acid, lauric acid,
- Capric acid caprylic acid, 2-ethylhexanoic acid, 2-octyldodecanoic acid, caproic acid, oleic acid, linoleic acid and linolenic acid, as well as coconut fatty acid, palm fatty acid, palm kernel fatty acid and tallow fatty acid, each preferably in cured or partially cured form. Also usable are mixtures of two or more of the aforementioned acids.
- the dicarboxylic acid of formula (I) will be succinic acid, maleic acid, glutaric acid, adipic acid or mixtures thereof; and / or as monocarboxylic acid of the formula (II) stearic acid, isostearic acid,
- Palmitic acid myristic acid, lauric acid, capric acid, caprylic acid, 2-ethylhexanoic acid, 2-octyldodecanoic acid, caproic acid, oleic acid, linoleic acid, linolenic acid, partially hardened coconut fatty acid, palm oil fatty acid, palm kernel fatty acid, tallow fatty acid and mixtures of 2, 3 or more of the aforementioned acids.
- Alkanolamines of the formula (III) which are suitable as central nitrogen compounds for the purposes of the invention contain a hydroxyalkane radical (alkanol radical) having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms.
- alkanol radical alkanol radical
- triethanolamine is used.
- the monocarboxylic acids (of formula II) and the dicarboxylic acids (of formula I) can be used in a molar ratio of 1:10 to 10: 1. However, it has proved to be advantageous to set a molar ratio of 1: 1 to 4: 1 and in particular 1, 5: 1 to 3: 1.
- Dicarboxylic acids - can be used in a molar ratio of 1: 1, 2 to 1: 2.4.
- esterification processes for providing the esterquats used according to the invention are generally known from the prior art.
- esterification can be carried out in a manner known per se, as described for example in International
- Patent application WO 91/01295 is described.
- the esterification takes place at temperatures of 120 to 220 ° C and in particular 130 to 170 ° C and pressures of 0.01 to 1 bar.
- Suitable catalysts are hypophosphorous acids or their alkali metal salts, preferably sodium hypophosphite, which are used in amounts of 0.01 to 0.1% by weight and preferably 0.05 to 0.07% by weight, based on the starting materials. can be used.
- alkali and / or alkaline earth boron hydrides such as potassium, magnesium and especially sodium borohydride has proven to be advantageous.
- co-catalysts are usually used in amounts of 50 to 1000 ppm and in particular 100 to 500 ppm - again based on the starting materials - a.
- Corresponding methods are also the subject of the two German Patent DE 4308792 C1 and DE 4409322 C1, the teachings of which are hereby incorporated by reference. It is possible to use in the esterification mixtures of monocarboxylic acids and dicarboxylic acids or esterification with the two components
- the quaternization of monocarboxylic acid / Dicarbonklaretrialkanolaminester can be carried out in a conventional manner.
- the reaction with the alkylating agents can also be carried out in the absence of solvents, it is recommended to use at least small amounts of water or lower alcohols, preferably isopropyl alcohol, to prepare concentrates which have a solids content of at least 80% by weight and in particular at least 90% % By weight.
- alkylating agents are alkyl halides such as methyl chloride, dialkyl sulfates such as dimethyl sulfate or diethyl sulfate or dialkyl carbonates such as
- Alkylating agent in a molar ratio of 1: 0.95 to 1: 1, 05, that is used approximately stoichiometrically.
- the reaction temperature is usually 40 to 80 ° C, and more preferably 50 to 60 ° C.
- it is advisable to destroy unreacted alkylating agent by adding, for example, ammonia, an (alkanol) amine, an amino acid or an oligopeptide, as described, for example, in German patent application DE 4026184 A1.
- the quaternizing agent is
- the at least one cationic compound comprises an esterquat compound of the formula (K1)
- X is a saturated or unsaturated hydrocarbon radical of 1 to 10
- the esterquats used according to the invention are ideally liquid to pasty at
- compositions according to the invention may contain the esterquats in amounts of from 2 to 60% by weight, preferably from 2 to 30% by weight, based on the total amount of the liquid composition, in the end product.
- Suitable thickening agents include, for example, Aerosil types (hydrophilic
- Silicic acids polysaccharides, in particular xanthan gum, guar guar, agar-agar, alginates and tyloses, carboxymethylcellulose, methylcellulose, hydroxypropyl, hydroxypropylmethyl and hydroxyethylcellulose, furthermore higher molecular weight polyethylene glycol mono- and diesters of fatty acids (eg Eumulgin® EO 33 of BASF), polyacrylates (eg Carbopole® from Goodrich or
- Synthalene® from Sigma polyacrylamides, polyvinyl alcohol and polyvinylpyrrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as
- pentaerythritol or trimethylolpropane fatty alcohol ethoxylates with narrow homolog distribution or Alkyloligoglucoside and electrolytes such as sodium chloride and
- the at least one thickener is a nonionic thickener, in particular selected from the group comprising hydroxyethylcellulose (HEC), hydroxypropylcellulose (HPC), hydroxypropylmethylcellulose (HPMC), methylcellulose (MC), guar, guar derivatives (such as Jaguar HP105 ( Rhodia), hydroxypropyl guar) and mixtures of the aforementioned nonionic thickeners.
- HEC hydroxyethylcellulose
- HPC hydroxypropylcellulose
- HPMC hydroxypropylmethylcellulose
- MC methylcellulose
- guar derivatives such as Jaguar HP105 ( Rhodia), hydroxypropyl guar
- the at least one thickener is a cationic copolymer.
- a copolymer may consist of or contain at least one monomer of the formula (M1) and at least one monomer of the formula (M2)
- R 5 , R 6 and R 7 are independently hydrogen or methyl
- A is ethane-1,2-diyl or propane-1,3-diyl and Y "is any anion.
- said copolymer is from 95 to 95 based on the total weight of the polymer
- Crosslinking is produced using at least one copolymerizable crosslinking agent.
- Suitable copolymerizable crosslinking agents carry at least two ethylenically unsaturated groups, and are selected, for example, from divinylbenzene, tetraallylammonium chloride, allyl acrylate, allyl methacrylate, diacrylate compounds of glycols, diacrylate compounds of polyglycols, dimethacrylate compounds of glycols, dimethacrylate compounds of
- Polyglycols butadiene, 1,7-octadiene, allylacrylamide, allylmethycrylamide, bisacrylamidoacetic acid, ⁇ , ⁇ '-methylenebisacrylamide, polyol polyallyl ethers and mixtures of two or more of these compounds.
- the copolymer can be obtained, for example, by emulsion polymerization.
- it is in the form of beads, wherein the beads preferably have an average particle diameter of 10 ⁇ to 1000 ⁇ , in particular from 50 ⁇ to 1000 ⁇ .
- the at least one thickener is a cationic copolymer using at least one copolymerizable
- Crosslinking agent having at least two ethylenically unsaturated groups, in particular selected from divinylbenzene, tetraallylammonium chloride, allyl acrylate, allyl methacrylate,
- Dimethacrylate compounds of glycols, dimethacrylate compounds of polyglycols, butadiene, 1, 7-octadiene, allylacrylamide, allylmethacrylamide, bisacrylamidoacetic acid, ⁇ , ⁇ '-methylenebisarylamide, Polyolpolyallylether, and mixtures of 2, 3 or more of these compounds is covalently crosslinked and / or a structure of general formula (IV)
- R 5 , R 6 and R 7 independently represent a hydrogen atom or a methyl group
- A is ethane-1, 2-diyl or propane-1,3-diyl and Y "is any anion.
- the at least one nonionic or cationic thickener in an amount of 0, 1 to 10 wt .-% based on the total weight of the composition contained therein.
- the at least one aminosiloxane is selected from the group comprising amodimethicone / morpholinomethyl silsesquioxane copolymer (CAS No. 1293390-78-9), trideceth-9 PG amodimethicone (CAS No. 943769-53-7) Methylsilsesquioxane Hydroxy-Limited Dimethyl, methyl (aminoethylaminoisobutyl) siloxane (CAS No. 863918-80-3) and dimethyl, methyl (aminoethylaminoisobutyl) siloxane (CAS No. 106842-44-8).
- amodimethicone / morpholinomethyl silsesquioxane copolymer CAS No. 1293390-78-9
- trideceth-9 PG amodimethicone CAS No. 943769-53-7
- the aminosiloxanes serve to improve the water absorption capacity
- the agent contains at least one
- the at least one emulsifier is preferably a nonionic emulsifier and has an HLB value of at least 12.0, preferably of at least 13.0, more preferably of at least 14.0, and most preferably of at least 15.0.
- HLB hydrophilic-lipophilic balance
- Low HLB values describe lipophilic substances
- high HLB values describe hydrophilic substances.
- defoamers typically have HLB values in the range of 1.5 to 3 and are insoluble in water.
- HLB values typically HLB values in the range of 3-8, whereas emulsifiers for O / W emulsions typically have HLB values in the range of 8-18.
- Detergent-active substances typically have HLB values in the range of 13-15 and solubilizer values in the range of 12-18.
- Molecular weight 200 to 5000 trimethylolpropane, pentaerythritol, sugar alcohols (eg sorbitol), alkylglucosides (eg methylglucoside, butylglucoside, laurylglucoside) as well as polyglucosides (eg cellulose) with saturated and / or unsaturated, linear or branched fatty acids with 12 to 22 carbon atoms and / or hydroxycarboxylic acids having 3 to 18 carbon atoms and their adducts with 1 to 30 moles of ethylene oxide;
- Glycosidrestes holds that both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol, as well as oligomeric glycosides having a degree of oligomerization to preferably about 8 are suitable.
- the degree of oligomerization is a statistical one
- Suitable partial glycerides are hydroxystearic acid monoglyceride,
- polyglycerol esters are polyglyceryl-2 dipolyhydroxystearates (Dehymuls® PGPH), polyglycerol-3-diisostearates (Lameform® TGI), polyglyceryl-4 isostearates (Isolan® Gl 34), polyglyceryl-3 oleates, diisostearoyl polyglyceryl-3 diisostearates (Isolan ® PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care® 450), Polyglyceryl-3 Beeswax (Cera Bellina®), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010 / 90), Polyglyceryl-3 Cetyl Ether (Chimexane® NL), Polyglyceryl -3 distearates (Cremophor® GS 32) and polyglyceryl polyricinoleates (Admul® WOL 1403) polyglyceryl dim
- compositions according to the invention may also contain further emulsifiers, for example cationic or anionic emulsifiers.
- Known cationic emulsifiers include fatty acid amidoamines and / or their quaternization products.
- R is CO-NR 2 - [(A) -NR 3 ] n -R 4 (V) where R is CO for a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms, R 2 is hydrogen or an optionally hydroxy-substituted alkyl radical with 1 to 4 carbon atoms, R 3 and R 4 independently of one another represent hydrogen, a (CH 2 CH 2 O) m H group or an optionally hydroxy-substituted alkyl radical having 1 to 4 carbon atoms, A represents a linear or branched alkylene group having 1 to 6
- R is CO for a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms
- R 2 is hydrogen or an optionally hydroxy-substituted alkyl radical having 1 to 4 carbon atoms
- R 3 is hydrogen, a (ChbChbC mH group or an optionally hydroxy-substituted Alkyl radical having 1 to 4 carbon atoms
- R 4 is R CO, hydrogen, a (ChbChhC mH group or an optionally hydroxy-substituted alkyl radical having 1 to 4 carbon atoms
- R 6 is an alkyl radical having 1 to 4 carbon atoms
- A is a linear or branched alkylene group with 1 to 6 carbon atoms
- n is from 1 to 4
- m is from 1 to 30
- X is halide, especially chloride, or alkyl
- emulsifiers include the betaines.
- Betaines are known surfactants which are predominantly produced by carboxyalkylation, preferably carboxymethylation of aminic compounds.
- the starting materials are condensed with halocarboxylic acids or their salts, in particular with sodium chloroacetate, wherein one mole of salt is formed per mole of betaine.
- unsaturated carboxylic acids such as acrylic acid
- R 8 is hydrogen or alkyl radicals having 1 to 4 carbon atoms
- R 9 is alkyl of 1 to 4 carbon atoms
- p is Numbers from 1 to 6
- A is an alkali and / or alkaline earth metal or ammonium.
- Typical examples are the carboxymethylation products of hexylmethylamine, hexyldimethylamine, octyldimethylamine, decyldimethylamine, dodecylmethylamine, dodecyldimethylamine,
- R 0 CO-NH- (CH 2 ) m -N + (R 8 ) (R 9 ) - (CH 2 ) P COOA (VIII)
- R 0 is CO for an aliphatic acyl radical having 6 to 22 carbon atoms and 0 or 1 to 3 double bonds
- m is from 1 to 3
- R 3 , R 9 , p and A are as defined above.
- Typical examples are reaction products of fatty acids having 6 to 22 carbon atoms, namely caproic acid, caprylic acid, capric acid, lauric acid,
- Elaidic acid petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and technical mixtures thereof, with N, N-dimethylaminoethylamine, N, N-dimethylaminopropylamine, ⁇ , ⁇ -diethylaminoethylamine and N, N-diethylaminopropylamine, with sodium chloroacetate be condensed.
- Preference is given to the use of a condensation product of Cs / is coconut fatty acid-N.N-dimethylaminopropylamide with sodium chloroacetate.
- R 5 is an alkyl radical having 5 to 21 carbon atoms
- R 6 is a hydroxyl group
- an OCOR 5 or NHCOR 5 radical and m is 2 or 3.
- These substances are also known substances which can be obtained, for example, by cyclizing condensation of 1 or 2 moles of fatty acid with polyhydric amines, such as, for example, aminoethylethanolamine (AEEA) or diethylenetriamine.
- AEEA aminoethylethanolamine
- the corresponding carboxyalkylation products are mixtures of different open-chain betaines.
- Typical examples are Condensation products of the abovementioned fatty acids with AEEA, preferably imidazolines based on lauric acid or, in turn, C 12/14 coconut fatty acid, which are subsequently mixed with
- compositions of the invention may betaine in amounts of 0.1 to 50, preferably 1 to 30 wt .-% and in particular 2 to 10 wt .-% - based on the
- Glycol ethers are also possible, provided that they are miscible with water in the concentration range used.
- the solvents are preferably selected from ethanol, n- or i-propanol, butanols, glycol, propane or butanediol, glycerol, diglycol, propyl- or butyldiglycol, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol propyl ether, etheylene glycol monomethyl n-butyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, propylene glycol methyl -, ethyl or -propyl ether, Dipropylenglykolmethyl-, or -ethylether, methoxy, ethoxy or
- the at least one nonaqueous solvent is selected from ethanol, propylene glycol,
- the agents of the invention further contain at least one hydrotrope.
- Suitable hydrotropes for the purposes of the invention are in particular aromatic alkyl sulfonates, in particular toluenesulfonates, cumene sulfonates, xylene sulfonates and the like. in question.
- the at least one hydrotrope is in particular an aromatic one
- Alkylsulfonic acid or an ester or salt thereof preferably selected from p-toluenesulfonic acid methyl ester, p-toluenesulfonic acid monohydrate and p-cumene sulfonic acid or the corresponding salts, in particular the sodium salts.
- the liquid composition has, in various embodiments, a viscosity of 100-300 mPas (20 ° C), wherein the viscosity is measured with a DV-II viscometer from Brookfield with spindle 2, at 20 rpm.
- compositions according to the invention contain further ingredients that further improve the performance and / or aesthetic properties of the composition depending on the intended use, for example as a fabric care or softener ,
- compositions additionally contain one or more substances from the group of electrolytes, pH adjusters, fragrances, perfume carriers, fluorescers, dyes, further hydrotopes, foam inhibitors, anti redeposition agents, enzymes, optical brighteners, grayness inhibitors, anti-shrinkage agents, anti-crease agents, color transfer inhibitors , antimicrobial agents, germicides, fungicides, antioxidants, corrosion inhibitors, antistatic agents, ironing aids, repellents and impregnating agents, swelling and anti-slip agents, cationic polymers and UV absorbers.
- Alkaline earth metals preferred anions are the halides and sulfates. From a manufacturing point of view, the use of NaCl or MgCb in the compositions according to the invention is preferred.
- Dyes and fragrances are added to the compositions according to the invention in order to improve the aesthetic impression of the products and to provide the consumer, in addition to the softness performance, with a visually and sensory "typical and unmistakable" product.
- perfume oils or fragrances individual fragrance compounds, e.g. the synthetic products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type are used. Fragrance compounds of the ester type are known e.g. benzyl acetate,
- Galbanum oil and labdanum oil as well as orange blossom oil, neroli oil, orange peel oil and
- the content of dyes is below 0.01 wt .-%, while fragrances can account for up to 2 wt .-% of the total formulation.
- perfume oils to be incorporated into the liquid formulations according to the invention are readily emulsifiable in order to be able to ensure the desired clear, transparent consistency of the formulation according to the invention.
- the agents according to the invention can be dyed with suitable dyes.
- Preferred dyes the choice of which presents no difficulty to the skilled person, have a high storage stability and insensitivity to the other ingredients of the agents and to light and no pronounced
- Suitable anti-redeposition agents which are also referred to as soil repellents, are, for example, nonionic cellulose ethers, such as methylcellulose and methylhydroxypropylcellulose having a proportion of methoxy groups of 15 to 30 wt .-% and hydroxypropyl groups of 1 to 15 wt .-%, each based on the nonionic
- Cellulose ethers and the known from the prior art polymers of phthalic acid and / or terephthalic acid or derivatives thereof, in particular polymers
- hydrotropes such as ethanol, isopropyl alcohol, or polyols can be used.
- Polyols contemplated herein preferably have from 2 to 15 carbon atoms and at least two hydroxyl groups.
- the polyols may contain other functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are:
- Methylol compounds in particular trimethylolethane, trimethylolpropane, trimethylolbutane pentaerythritol and dipentaerythritol,
- Lower alkyl glucosides in particular those having 1 to 8 carbons in the alkyl radical, such as, for example, methyl and butyl glucoside,
- Sugar alcohols having 5 to 12 carbon atoms such as sorbitol or mannitol,
- Sugar with 5 to 12 carbon atoms such as, for example, glucose or sucrose
- Dialcoholamines such as diethanolamine or 2-amino-1,3-propanediol.
- Endoglucanases and ß-glucosidases which are also called cellobiases, or mixtures thereof used. Since different types of cellulases differ in their CMCase and avicelase activities, targeted mixtures of the cellulases can be used to set the desired activities.
- the enzymes may be adsorbed to carriers or embedded in encapsulants to protect against premature degradation.
- the proportion of enzymes, enzyme mixtures or enzyme granules may be, for example, about 0.1 to 5 wt .-%, preferably 0, 12 to about 2 wt .-%.
- Optical brighteners can be added to the compositions according to the invention in order to eliminate graying and yellowing of the treated textiles. These fabrics impinge on the fiber and cause whitening and bleaching by transforming invisible ultraviolet radiation into visible longer wavelength light, emitting ultraviolet light absorbed from the sunlight as faint bluish fluorescence, and pure yellow with the yellowed or yellowed wash White results.
- Compounds originate, for example, from the substance classes of 4,4'-diamino-2,2'-stilbenedisulfonic acids (flavonic acids), 4,4'-distyrylbiphenyls, methylumbelliferones, coumarins, dihydroquinolinones, 1,3-diarylpyrazolines, naphthalimides, benzoxazole, Benzisoxazole and benzimidazole systems and substituted by heterocycles pyrene derivatives.
- the optical brighteners are usually used in amounts between 0, 1 and 0.3 wt .-%, based on the finished composition.
- compositions according to the invention may contain synthetic anti-crease agents.
- bacteriostats and bactericides, fungistats and fungicides, etc.
- Important substances from these groups are, for example, benzalkonium chlorides.
- Preferred compounds in the context of the present invention are, for example, alkylaryl sulfonates, halophenols and phenol mercuriacetate, it also being possible entirely to dispense with these compounds in the compositions according to the invention.
- the agents may contain antioxidants.
- This class of compounds includes, for example, substituted phenols, hydroquinones, catechols and aromatic amines, as well as organic sulfides, polysulfides, dithiocarbamates, phosphites and phosphonates.
- External antistatics are usually substances with at least one hydrophilic
- Molecule ligands and give a more or less hygroscopic film on the surfaces.
- These mostly surface-active antistatic agents can be subdivided into nitrogen-containing (amines, amides, quaternary ammonium compounds), phosphorus-containing (phosphoric acid esters) and sulfur-containing (alkyl sulfonates, alkyl sulfates) antistatic agents.
- External antistatic agents are for example in the Patent applications FR 1, 156,513, GB 873,214 and GB 839,407.
- the lauryl (or stearyl) dimethylbenzylammonium chlorides disclosed herein are useful as antistatics for textiles or as additives to laundry detergents, with the additional benefit of providing a softening effect.
- Cationic polymers in the context of the present invention are polymers which carry a positive charge in the polymer molecule. This can be realized, for example, by (alkyl) ammonium groups or other positively charged groups present in the polymer chain.
- Particularly preferred cationic polymers come from the groups of quaternized cellulose derivatives, the polysiloxanes with quaternary groups, the cationic guar derivatives, the polymeric dimethyldiallylammonium salts and their copolymers with esters and amides of acrylic acid and methacrylic acid, the copolymers of vinylpyrrolidone with quaternized derivatives of dialkylamino and methacrylates, the vinylpyrrolidone-methoimidazolinium chloride copolymers, the quaternized polyvinyl alcohols or the names
- the agents according to the invention may also contain UV absorbers which are absorbed by the treated textiles and improve the light resistance of the fibers.
- UV absorbers which are absorbed by the treated textiles and improve the light resistance of the fibers.
- Compounds having these desired properties include, for example, the non-radiative deactivating compounds and derivatives of benzophenone having substituents in the 2- and / or 4-position.
- phenyl-substituted acrylates (cinnamic acid derivatives), optionally with cyano groups in the 2-position, salicylates, organic Ni complexes and natural substances such as umbelliferone and the body's own urocanic acid.
- preservatives In order to achieve optimal performance characteristics and to protect the products against germs, it may be advantageous to add preservatives to the products. Infestation of the fabric softeners according to the invention by microorganisms can be prevented by the use of commercially available preservatives.
- the total proportion of the additives may be from 1 to 50% by weight, preferably from 5 to 40% by weight, based on the end product.
- the invention is further directed, as described above, to the use of components (a), (b) and (c) for the preparation of liquid, clear, homogeneous and fabric softening
- Textile treatment agents and corresponding production methods may be carried out according to techniques known to those skilled in the art of fabric care products and fabric softeners. This can be done for example by mixing the raw materials, optionally using high-shear mixing equipment.
- the invention also relates to processes for the treatment of textiles.
- at least one textile is contacted with a liquid composition as described herein.
- liquid compositions as described herein for the care and / or conditioning of fabrics.
- the exemplary embodiments show that the use of aminosiloxanes can reduce the amount of esterquat in the agents according to the invention without significantly changing the properties of the agents according to the invention.
- all the agents according to the invention have no turbidity and a good viscosity, which prevents the formation of thread.
- Viscosity (Brookfield 100-300 100-300 100-300 100-300 100-300 100-300 100-300 100-300 100-300 100-300
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Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE102014226192 | 2014-12-17 | ||
DE102015204206.5A DE102015204206A1 (de) | 2014-12-17 | 2015-03-10 | Transparente Textilpflegemittel |
PCT/EP2015/079286 WO2016096614A1 (de) | 2014-12-17 | 2015-12-10 | Transparente textilpflegemittel |
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EP3234087A1 true EP3234087A1 (de) | 2017-10-25 |
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EP15808384.0A Withdrawn EP3234087A1 (de) | 2014-12-17 | 2015-12-10 | Transparente textilpflegemittel |
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US (1) | US10377967B2 (de) |
EP (1) | EP3234087A1 (de) |
KR (1) | KR20170095319A (de) |
AU (1) | AU2015366486A1 (de) |
DE (1) | DE102015204206A1 (de) |
WO (1) | WO2016096614A1 (de) |
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EP3263680B1 (de) * | 2016-06-30 | 2018-08-15 | Henkel AG & Co. KGaA | Klare textilpflegemittel |
US11466400B2 (en) * | 2018-06-19 | 2022-10-11 | Hexcel Corporation | Finish composition |
US20220348845A1 (en) * | 2019-09-27 | 2022-11-03 | Church & Dwight Co., Inc. | Liquid fabric softening composition |
CA3187407A1 (en) * | 2020-07-31 | 2022-02-03 | Sandra Paola SANCHEZ | Fabric softening compositions |
US20230140936A1 (en) * | 2021-11-05 | 2023-05-11 | Henkel IP & Holding GmbH | Fabric Softening Composition Comprising Germicidal Cationic Surfactants |
EP4239043A1 (de) | 2022-03-01 | 2023-09-06 | Kao Corporation S.A.U | Dispergierbare weichmacherformulierungen und einheitsdosen |
EP4239041A1 (de) | 2022-03-01 | 2023-09-06 | Kao Corporation S.A.U | Klare weichspülerformulierungen |
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FR1156513A (fr) | 1956-07-24 | 1958-05-19 | Préparation permettant d'éliminer l'électricité statique des fibres textiles de synthèse | |
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GB873214A (en) | 1958-08-20 | 1961-07-19 | British Nylon Spinners Ltd | Non-ionic detergent compositions |
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DE2024051C3 (de) | 1970-05-16 | 1986-05-07 | Henkel KGaA, 4000 Düsseldorf | Verwendung der Veresterungsprodukte von Glycerin-Äthylenoxid-Addukten mit Fettsäuren als Rückfettungsmittel in kosmetischen Zubereitungen |
ES2021900A6 (es) | 1989-07-17 | 1991-11-16 | Pulcra Sa | Procedimiento de obtencion de tensioactivos cationicos derivados de amonio cuaternario con funcion amino-ester. |
DE4026184A1 (de) | 1990-08-18 | 1992-02-20 | Henkel Kgaa | Verfahren zur verminderung des restgehaltes an freiem alkylierungsmittel in waessrigen loesungen kationischer tenside |
DE4308792C1 (de) | 1993-03-18 | 1994-04-21 | Henkel Kgaa | Verfahren zur Herstellung farb- und geruchstabiler quaternierten Fettsäuretriethanolaminester-Salze |
DE4409322C1 (de) | 1994-03-18 | 1995-04-06 | Henkel Kgaa | Verfahren zur Herstellung von Esterquats |
DE19751151A1 (de) | 1997-11-19 | 1999-05-20 | Henkel Kgaa | Klare Weichspüler mit mikroemulgierten Parfümölen |
DE19962874A1 (de) * | 1999-12-24 | 2001-06-28 | Cognis Deutschland Gmbh | Transparente Avivagemittel |
ES2180372B1 (es) * | 2000-03-22 | 2003-10-16 | Kao Corp Sa | Esteres derivados de alcanolaminas, acidos dicarboxilicos y alcoholes grasos, y los tensioactivos cationicos obtenibles a partir de los mismos. |
DE10115476A1 (de) * | 2001-03-29 | 2002-10-10 | Wacker Chemie Gmbh | Verfahren zur Behandlung von organischen Fasern |
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2015
- 2015-03-10 DE DE102015204206.5A patent/DE102015204206A1/de active Pending
- 2015-12-10 US US15/539,837 patent/US10377967B2/en active Active
- 2015-12-10 KR KR1020177019350A patent/KR20170095319A/ko unknown
- 2015-12-10 WO PCT/EP2015/079286 patent/WO2016096614A1/de active Application Filing
- 2015-12-10 EP EP15808384.0A patent/EP3234087A1/de not_active Withdrawn
- 2015-12-10 AU AU2015366486A patent/AU2015366486A1/en not_active Abandoned
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KR20170095319A (ko) | 2017-08-22 |
DE102015204206A1 (de) | 2016-06-23 |
AU2015366486A1 (en) | 2017-07-20 |
WO2016096614A1 (de) | 2016-06-23 |
US10377967B2 (en) | 2019-08-13 |
US20180094213A1 (en) | 2018-04-05 |
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