WO2000006678A1 - Composition useful for softening, cleaning, and personal care applications - Google Patents
Composition useful for softening, cleaning, and personal care applications Download PDFInfo
- Publication number
- WO2000006678A1 WO2000006678A1 PCT/US1999/016981 US9916981W WO0006678A1 WO 2000006678 A1 WO2000006678 A1 WO 2000006678A1 US 9916981 W US9916981 W US 9916981W WO 0006678 A1 WO0006678 A1 WO 0006678A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- reaction mixture
- alkanolamine
- percent
- alkyl group
- formula
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 126
- 238000004140 cleaning Methods 0.000 title description 10
- 239000011541 reaction mixture Substances 0.000 claims abstract description 61
- 239000003599 detergent Substances 0.000 claims abstract description 28
- 238000005886 esterification reaction Methods 0.000 claims abstract description 16
- 239000002979 fabric softener Substances 0.000 claims abstract description 13
- 238000009472 formulation Methods 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 239000004744 fabric Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 150000005690 diesters Chemical class 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- -1 organic acid anion Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 150000005691 triesters Chemical class 0.000 claims description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
- 239000011630 iodine Substances 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 230000032050 esterification Effects 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 150000007522 mineralic acids Chemical group 0.000 claims description 6
- 239000012669 liquid formulation Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 3
- 239000001913 cellulose Substances 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000002253 acid Substances 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 17
- 239000000463 material Substances 0.000 description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
- 239000004902 Softening Agent Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 8
- 229940088598 enzyme Drugs 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000007844 bleaching agent Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000003301 hydrolyzing effect Effects 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 229940050176 methyl chloride Drugs 0.000 description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 5
- 239000002738 chelating agent Substances 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000002752 cationic softener Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- PVXVWWANJIWJOO-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-N-ethylpropan-2-amine Chemical compound CCNC(C)CC1=CC=C2OCOC2=C1 PVXVWWANJIWJOO-UHFFFAOYSA-N 0.000 description 2
- XKEVWMVUIDDRMC-UHFFFAOYSA-N 3,4-methylenedioxy-n-isopropylamphetamine Chemical compound CC(C)NC(C)CC1=CC=C2OCOC2=C1 XKEVWMVUIDDRMC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QMMZSJPSPRTHGB-UHFFFAOYSA-N MDEA Natural products CC(C)CCCCC=CCC=CC(O)=O QMMZSJPSPRTHGB-UHFFFAOYSA-N 0.000 description 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241000350481 Pterogyne nitens Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000003254 anti-foaming effect Effects 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 229910001424 calcium ion Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 150000005829 chemical entities Chemical class 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229910001425 magnesium ion Inorganic materials 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- HMXKBJSSOJHDDI-UHFFFAOYSA-N 1-[2-hydroxybutyl(2-hydroxyethyl)amino]butan-2-ol Chemical compound CCC(O)CN(CCO)CC(O)CC HMXKBJSSOJHDDI-UHFFFAOYSA-N 0.000 description 1
- HHKUQCFQGCCLGA-UHFFFAOYSA-N 1-[2-hydroxyethyl(2-hydroxypropyl)amino]propan-2-ol Chemical compound CC(O)CN(CCO)CC(C)O HHKUQCFQGCCLGA-UHFFFAOYSA-N 0.000 description 1
- UTQDHZMLKBOPTL-UHFFFAOYSA-N 1-[2-hydroxyethyl(methyl)amino]butan-2-ol Chemical compound CCC(O)CN(C)CCO UTQDHZMLKBOPTL-UHFFFAOYSA-N 0.000 description 1
- XKDVKNSEIYCSAL-UHFFFAOYSA-N 1-[bis(2-hydroxyethyl)amino]butan-2-ol Chemical compound CCC(O)CN(CCO)CCO XKDVKNSEIYCSAL-UHFFFAOYSA-N 0.000 description 1
- ZFECCYLNALETDE-UHFFFAOYSA-N 1-[bis(2-hydroxyethyl)amino]propan-2-ol Chemical compound CC(O)CN(CCO)CCO ZFECCYLNALETDE-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- OEBOTDIKXIRPJB-UHFFFAOYSA-N CC(O)CN.CC(C)(O)N Chemical group CC(O)CN.CC(C)(O)N OEBOTDIKXIRPJB-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 102000005575 Cellulases Human genes 0.000 description 1
- 108010084185 Cellulases Proteins 0.000 description 1
- LXBIFEVIBLOUGU-UHFFFAOYSA-N Deoxymannojirimycin Natural products OCC1NCC(O)C(O)C1O LXBIFEVIBLOUGU-UHFFFAOYSA-N 0.000 description 1
- 239000004667 Diesterquat Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021353 Lignoceric acid Nutrition 0.000 description 1
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- BCXBKOQDEOJNRH-UHFFFAOYSA-N NOP(O)=O Chemical class NOP(O)=O BCXBKOQDEOJNRH-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
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- 229920000388 Polyphosphate Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
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- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
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- 125000000129 anionic group Chemical group 0.000 description 1
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- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
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- JDZNTUQRMDAIRO-UHFFFAOYSA-N dimethylmyleran Chemical compound CS(=O)(=O)OC(C)CCC(C)OS(C)(=O)=O JDZNTUQRMDAIRO-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
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- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
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- 239000003623 enhancer Substances 0.000 description 1
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- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
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- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
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- 239000003752 hydrotrope Substances 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 229910001437 manganese ion Inorganic materials 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000004669 nonionic softener Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000013503 personal care ingredient Substances 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/42—Amino alcohols or amino ethers
-
- 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
- C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
-
- 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
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/22—Agents rendering paper porous, absorbent or bulky
- D21H21/24—Surfactants
Definitions
- the present invention relates to a process for manipulating esterification reactions of alkanolamines to favor the formation of either the monoester or diester at the expense of the formation of higher esters.
- This process produces heretofore unknown reaction mixtures which can be advantageously used in laundry, cleaner, or personal care applications.
- the present invention relates to alkoxylated ester-amine compositions, the protonated or quatemized forms thereof, and processes for the preparation of the same.
- esterquats are known as cationic fabric softening agents. See, for example, WO-A-93/25648, DE-A-4,339,643 and US-A-4,339,391 ; US-A-4,767,547, US- A-4,874,554 and US-A-5,066,414.
- Other examples of known quatemized ester-amines include US-A-5,463,094, which discloses quaternary ammonium compounds which the starting tertiary amine can include carboxylic esters of hydroxyalkyl groups.
- 97 105 620.5 teaches a family of esterified alkanolamines prepared by first alkoxylating an alkanolamine having from 1 to 3 OH groups with alkylene oxides having from 2 to 6 carbons, then esterifying the compounds.
- 97/42279 to make such compositions requires the use of 1.6 to 1.8 moles of unsaturated fatty acids per mole of trialkanol amine.
- the unsaturated fatty acid is required to have a high level of the cis isomer, or an isomerizing step to convert esters to the desired cis/trans configuration.
- This reference also teaches a controlled heating protocol which is necessary in order to achieve the desired goal of high diester.
- DE-A-4,243,701 discloses that beneficial fabric softening properties can be seen from the diesterquat of triethanolamine (TEA), but this reference provides no method for obtaining such diesters in a reaction mixture.
- WO-A-97/03160 indicates the benefits of having cationic ester surfactants in laundry detergents. These benefits include superior greasy cleaning and improved antiredeposition of soils during the wash process.
- CET cationic ester surfactants
- Reaction mixtures made according to the present invention exhibit improved softening or detergency properties and are more hydrolytically stable than reaction mixtures of the prior art. This makes them well-suited for use in fabric softeners, paper softeners, cleaners, detergents, and personal care applications.
- a lower alkanolamine i.e. a primary or secondary amine
- a lower alkanolamine is alkoxylated with an alkylene oxide or a mixture of alkylene oxides, then esterified with a carboxylic acid, and then optionally neutralized or quatemized.
- the alkanolamines suitable as the starting material for this embodiment of the invention have the structure: ( C R ' R 2 ) n - C R 3 R 4 0 H
- R 1 , R 2 , R 3 and R 4 are independently in each moiety H or an alkyl group; n is independently in each moiety a number equal to 1 or greater; R 1 , R 2 , R 3 , R 4 and n are such that the number of carbon atoms between N and O is no more than 18; R 7 is H or R 5 ; and R 5 is (CR 1 R 2 ) n -CR 3 R 4 -OH, an alkyl having from 1-6 carbon atoms, a cycloalkyl having 6 carbon atoms, or an aryl group.
- the alkylene oxides suitable for use in the present invention correspond to the formula C y H 2y O, where y is from 2 to 18, preferably 2 to 6.
- the materials are chosen such that if y is only 2 then for at least some of the lower alkanolamines in the mixture, in at least one moiety on the N group, R 3 or R 4 will be an alkyl group.
- a reaction mixture is prepared which has a higher proportion of diester or monoester, at the expense of the completely esterified alkanolamine, than previously reported.
- the process of the invention can produce reaction mixtures having greater than 50 percent by weight of the diester component.
- the monoester portion in the final reaction mixture can represent 60 percent or more by weight of the total reaction mixture.
- compositions of the present invention exhibit surprisingly high hydrolytic stability over a wide pH range, have unexpectedly low melting points, are more compatible with detergent and personal care ingredients and they can be more easily handled either in the diluted form or formulated as stable liquid concentrates as compared to corresponding reaction mixtures made from di- or tri-ethanolamines. Accordingly, in another embodiment of the present invention these compounds are used in such applications as fabric softeners, paper softeners, detergents, cleaners and personal care items.
- the composition of the present invention comprises a reaction mixture comprising monoester (II), diester (III), triester (IV) and optionally free alkanolamine (I) components corresponding to the following formulae:
- R is an alkyl group having 1 to 30 carbons
- R 1 , R 2 , R 3 and R 4 are independently in each moiety H or an alkyl group provided that R 3 and R 4 are not all H in all of the moieties;
- n is independently in each moiety a number equal to 1 or greater;
- n and R 1 , R 2 , R 3 and R 4 are such that the number of carbon atoms between N and O is no more than 18;
- R 5 is (CR 1 R 2 ) n -CR 3 R 4 -OH, an alkyl having from 1 -6 carbon atoms, a cycloalkyl having 6 carbon atoms, or an aryl group;
- Q is H, an alkyl group having 1 to 6 carbons, or an aryl group having 6-12 carbons, optionally substituted with an alkyl group, or HOCHR 6 CH 2 -, wherein R 6 is H or an alkyl group having 1 to 4 carbons;
- X is an inorganic or organic acid anion;
- reaction mixture having been prepared at least in part from the esterification of an alkanolamine corresponding to the formula:
- composition of the present invention comprises a reaction mixture comprising monoester (II), diester (III), triester (IV) and, optionally, free alkanolamine (I) components corresponding to the following formulae:
- R is an alkyl group having 1 to 30 carbons
- R ⁇ R 2 , R 3 and R 4 are independently in each moiety H or an alkyl group provided that R 3 and R 4 are not all H in all of the moieties in the reaction mixture;
- n is independently in each moiety a number equal to 1 or greater;
- n and R 1 , R 2 , R 3 and R 4 are such that the number of carbon atoms between N and O is no more than 18;
- R 5 is (CR R 2 ) n -CR 3 R 4 -OH, an alkyl having from 1-6 carbon atoms, a cycloalkyl having 6 carbon atoms, or an aryl group;
- Q is H, an alkyl group having 1 to 6 carbons, or an aryl group having 6-12 carbons, optionally substituted with an alkyl group, or HOCHR ⁇ CH 2 -, wherein R 6 is H or an alkyl group having 1 to 4 carbons;
- X is an inorganic or organic acid anion
- p is from O to l ,
- reaction mixture having been prepared at least in part from the esterification of an alkanolamine corresponding to the formula:
- composition includes both a single chemical entity and mixtures of chemical entities which correspond to the same general formula.
- moiety means a group of inter-connected atoms which is attached to the central nitrogen atom.
- R have from 4-24 carbon atoms, and more preferred that R have from 7-22 carbon atoms.
- the R group may be straight or branched, and may have different levels of saturation. Generally, it is preferred that the R group have an Iodine value less than 140. Iodine values can be calculated by ways known in the art. For some applications, such as concentrated fabric softeners or clear transparent formulations, it is generally preferred that the R group have Iodine values greater than 20, but in other applications, such as detergents, Iodine values less than 20, including fully saturated R groups can be advantageously used. For general, less concentrated fabric softener use, the Iodine values have not been shown to have a significant effect and so all ranges may be used.
- n be equal to 1 , especially in those moieties where R 3 or R 4 is an alkyl group. It is also preferred that R 1 and R 2 are H. It is also generally preferred that not both R 3 and R 4 are alkyl groups in the same moiety. Furthermore it is preferred that when R 3 or R 4 is an alkyl group, it is an alkyl group having 1 or 2 carbons. It is also preferred that n and R 1 , R 2 , R 3 and R 4 are such that the number of carbon atoms between N and O is no more than 6.
- p represents an average, showing the degree of neutralization or quatemization, but that for any particular molecule, it will be 0 or 1. It is also within the scope of this invention to not quaternize the reaction mixture at all, although this is not preferred.
- the invention comprises a procedure to make esterified alkanolamines, wherein the reaction mixture will have a disproportionate amount of not fully esterified product than would normally be expected.
- the procedure comprises esterifying an alkanolamine (or mixtures thereof) corresponding to the following formula:
- n is independently in each moiety a number equal to 1 or greater;
- n and R 1 , R 2 , R 3 and R 4 are such that the number of carbon atoms between N and O is no more than 18;
- R 5 is (CR 1 R 2 ) n -CR 3 R 4 -OH, an alkyl having from 1-6 carbon atoms, a cycloalkyl having 6 carbon atoms, or an aryl group.
- the alkanolamine is formed by alkoxylating a primary or secondary alkanolamine (or mixtures thereof) with one or more alkylene oxides where the primary or secondary alkanolamine corresponds to the formula:
- R 1 , R 2 , R 3 and R 4 are independently in each moiety H or an alkyl group; n is independently in each moiety a number equal to 1 or greater; n, R 1 , R 2 , R 3 and R 4 are such that the number of carbon atoms between N and O is no more than 18; R 7 is H or R 5 ; and R 5 is (CR , R 2 ) n -CR 3 R 4 -OH, an alkyl having from 1-6 carbon atoms, a cycloalkyl having 6 carbon atoms, or an aryl group; and the alkylene oxide corresponds to the formula C y H 2y O, where y is from 2 to 18, preferably 2 to 6.
- the materials are chosen such that if y is only 2 then for at least some of the lower alkanolamines in the mixture, in at least one moiety on the N group, R 3 or R 4 will be an alkyl group. It is preferred that n be equal to 1 , especially in those moieties where R 3 or R 4 are an alkyl group. It is also preferred that R 1 and R 2 are H. It is also generally preferred that not both R 3 and R are alkyl groups in the same moiety. Furthermore it is preferred that when R 3 or R 4 is an alkyl group, it is an alkyl group having 1 or 2 carbons. It is also preferred that n and R 1 , R 2 , R 3 and R 4 are such that the number of carbon atoms between N and O is no more than 6.
- Preferred alkylene oxides include ethylene oxide, propylene oxide and butylene oxide.
- this alkoxylation reaction process may be carried out in the presence of an alkaline catalyst, such as sodium, potassium, calcium, barium and strontium hydroxide, in an amount of from 0.01 to 5, preferably 0.1 to 0.5, percent by weight based on the total weight of the mixture at the completion of the reaction. Care must be taken when using catalyst not to alkoxylate the OH groups, and so in general, the use of catalyst is not preferred for this invention.
- an alkaline catalyst such as sodium, potassium, calcium, barium and strontium hydroxide
- Temperature and pressures are not critical, but conveniently the alkoxylation reaction is carried out at an elevated 5 temperature, preferably at a temperature from 50°C to 200°C, more preferably from 80°C to 120°C and a pressure of from 1 to 80 bars.
- the alkaline catalysts suitable for use in this reaction are well known to a person skilled in the art. After completion of the reaction, that is, for example, when the pressure does not change any more, the catalyst is removed by a suitable method, such as by filtration over an absorbing clay, 0 for example, magnesium silicate, or neutralized with an inorganic acid such as, for example, hydrochloric acid, or an organic acid such as, for example, acetic acid. If desired, an excess of an acid can be used, so that the excess of the acid can serve as a catalyst in the subsequent reaction step. It is advantageous to carry out the alkoxylation reaction in the presence of a defoaming agent.
- the esterification reaction comprises contacting the alkanolamine with a carboxylic acid (or a mixture of carboxylic acids) under conditions sufficient to cause at least a portion of the carboxylic acid to react with at least a portion of the OH groups on the alkanolamine so as to form esters.
- the carboxylic acid corresponds to the formula RCOOH, where R is an alkyl group having 1 to 30 carbons. It is preferred that R have o from 4-24 carbon atoms, and more preferred that R have from 7-22 carbon atoms.
- R group may be straight or branched, and may have different levels of saturation. Generally, it is preferred that the R group have an Iodine value less than 140. Iodine values can be calculated by ways known in the art. For some applications it is preferred that the R group have Iodine values greater than 20, but in other applications, Iodine 5 values less than 20, including fully saturated R groups can be advantageously used. Where unsaturated R groups are used, it is preferred that the ratio of the cis to trans isomer be 80:20 or greater.
- carboxylic acids useful in the esterification reaction include valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, and o lignoceric acid, and the branched isomers thereof (isovaleric acid, for example), or the unsaturated isomers thereof (for example, oleic acid).
- fatty acids are well-known to the person of ordinary skill in the art.
- the esterification reaction conveniently is carried out at an elevated temperature, preferably at a temperature from 50°C to 250°C, more preferably from 5 180°C to 220°C, and reduced pressure, preferably from 1 to 500 mbar, more preferably from 20 to 200 mbar.
- elevated temperature preferably at a temperature from 50°C to 250°C, more preferably from 5 180°C to 220°C
- reduced pressure preferably from 1 to 500 mbar, more preferably from 20 to 200 mbar.
- the acid be added in an amount of from 0.5 to 0.7 moles of carboxylic acid per mole of OH on the alkanolamine (1.5 to 2.1 moles acid per mole trialkanolamine).
- reaction mixtures of trialkanolamines with a diester content greater than 50 percent by weight can be observed even when adding the acid at ratios of greater than 1.8 moles of acid per mole of trialkanolamine (0.6 moles of acid per mole equivalent of trialkanolamine) or less than 1.6 moles of acid per mole of trialkanolamine (0.53 moles of acid per mole equivalent of trialkanolamine).
- reaction mixtures having greater than 55 percent by weight can be obtained. If a monoester of a dialkanol amine is desired, then it is preferred that the acid be added in an amount of from 0.4 to 1.1 moles of acid per mole of dialkanol amine (0.2 to 0.55 moles of acid per mole of OH on the dialkanol amine). At these ratios, reaction mixtures having greater than 60 percent monoester can be obtained.
- the esterified alkanolamines can then be neutralized or quatemized by contacting the esterified alkanolamines with a composition corresponding to the formula QX, under conditions sufficient to cause at least a portion of the esterified alkanolamines to form a quatemized, or neutralized product.
- Q in the above formula is H, an alkyl group having 1 to 6 carbons, or an aryl group having 6-12 carbons, optionally substituted with an alkyl group, or HOCHR 6 CH 2 -, wherein R 6 is H or an alkyl group having 1 to 4 carbons; and X is an inorganic or organic acid anion.
- the neutralization reaction is preferably carried out at the molar ratio of from 0.05 to 2 moles QX per mole of esterified alkanolamine. Such a reaction can be carried out at room temperature or above the melting point of the alkoxylated ester-amine compound, and at a pressure of from 1 to 50 bars.
- the quatemization reaction is preferably carried out at the ratio of from 0.1 to 20 moles QX per mole of esterified alkanolamine, at a temperature of from 30°C to 150°C, and a pressure of from 1 to 50 bars.
- Any known inorganic acid such as, for example, hydrochloric acid, or organic acid such as, for example, citric acid can be used as the HX compound to protonate the alkoxylated ester-amine (see for example, WO-A- 94/04641 and WO-A-94/04642).
- Any known quatemizing agent can be used as the QX compound.
- Suitable quatemizing agents of formula QX include alkyl halides, dialkyl sulfates, and trialkyl phosphates.
- Preferred alkyl halides include methyl chloride, ethyl chloride, methyl bromide, and ethyl bromide; preferred dialkyl sulfates include dimethyl sulfate, and diethyl sulfate, and preferred trialkyl phosphates include trimethyl phosphate and triethyl phosphate. It is advantageous to carry out the quatemization reaction in the presence of a defoaming agent. It can also be advantageous to carry out the quatemization reaction in the presence of an additive which can lower the melting point of the reaction mixture, as is known in the art. These additives can be added at any stage of the reaction.
- Suitable additives include materials such as water, isopropanol, propanediol, dipropylene glycol, PEG, PPG, alkoxylated fatty acids and alcohols having more than 3 carbons in the fatty chain, glycol ether solvents such as DOWANOLTM P and E series, diether solvents such as PROGLYDETM DMM, tetrahydrofuran, methanol, ethanol, hexanediol, and acetone.
- compositions of the present invention exhibit good softening, detergency, antifoaming and antistatic properties, they have low melting points, and are hydrolytically stable at various pH values.
- the compositions of the invention which have higher diester content tend to be especially well suited for the fabric and paper softening applications, while those compositions with high monoester content tend to show improved detergency properties.
- hydrolytically stable means that less than 30 percent, preferably less than 20 percent, of composition of Formulas (l-IV) above when Q is not H and p is greater than 0.75 and less than 40 percent of a composition of Formulas (l-IV) above when p is 0, or Q is H, hydrolyzes after 4 weeks from a 5 percent aqueous solution having a pH value of 4, at a temperature of 50°C.
- hydrolytically stable means that less than 45 percent, preferably less than 30 percent hydrolyzes after 4 weeks from a 5 percent aqueous solution having a pH value of 4, at a temperature of 50°C, when p is greater than 0.8. It should be understood that the extent of hydrolysis defined above is valid for a value of pH 4 and that hydrolysis extent would decrease with decreasing pH and increase with increasing pH.
- the improved hydrolytic stability of the compositions of the present invention allow them to be used in liquid or gel detergent, softergent or softener formulations.
- compositions of the present invention are compatible even with fabric and paper softeners' ingredients and detergents ingredients which are normally not compatible with known softening compounds without the presence of special additives. Due to these properties the composition mixtures of the present invention can be formulated into formulations suitable for various end use applications such as, for example, fabric and paper softening formulations, formulation for cleaning and conditioning fabric materials ("softergents"), antifoaming formulations, personal care formulations, lubricating formulations, drilling fluid formulations and hard surface cleaning formulations.
- the present invention concerns a fabric softening, paper softening, detergent, personal care, or cleaner formulation comprising the composition of the invention.
- the formulations of the present invention can also incorporate one or more known ingredients commonly used in fabric softening, paper softening, detergent, personal care or cleaner formulations.
- the fabric and paper softening formulations of the present invention can be in various forms, such as, for example, aqueous or anhydrous liquid formulations, super concentrate liquid formulations, solid formulations obtained by a suitable process such as grinding the softener composition or depositing it onto solid substrates such as powders or granules, or onto cellulosic substrate sheets for use in tumble dryers.
- the fabric softening formulations can be used in a tumbler dryer or in the rinse cycle in a washing machine for example by dispensing the fabric softening formulation via a dispensing compartment optionally with dilution prior to dosing into the dispensing compartment.
- the fabric and paper softening formulations of the present invention which have a pH below 8 when diluted for normal use conditions are preferred. Normal use conditions are known in the art but are generally in the range of from 0.01 to 0.5 percent by weight active ingredient, and most commonly about 0.05 percent.
- the present invention concerns an anhydrous or aqueous fabric and paper softening formulation comprising at least 0.01 , preferably from 0.01 to 95 percent by weight the composition of the invention.
- the liquid fabric and paper softening formulations of the present invention may be prepared by mixing the composition of the invention with a liquid carrier and, optionally, at least one other above mentioned ingredient in a standard formulation mixing equipment and in accordance with techniques known to a person skilled in the art. Low-shear mixing is generally sufficient to adequately and uniformly mix the softening composition within the softening formulation.
- the final softening formulation, whether in concentrated or diluted form must be easily pourable by the end user.
- the formulation may be formulated to be diluted (for example, for refill packs) by a factor of generally 4:1 or more, preferably up to 8:1 or even up to 20:1.
- fabric softener formulations contain normally from 5 to 20 percent of softening agent. They are normally opaque milky emulsions of various viscosities. In general the viscosity of fabric softening formulations increase with the increase in concentration of its fabric softening agent. Additives are normally used to stabilize more concentrated fabric softening formulations (for example, those containing between 10 and 20 percent softening agent). It should be noted that WO-A-96/21715 teaches the use of special deflocculating nonionic polymeric surfactants to allow incorporation of up to 35 percent of a softening agent. The absence of additives would lead to gelling of softening formulations containing more than 15 percent of a softener agent.
- compositions of the present invention which have a high diester content have unexpectedly higher hydrolytic stability than known softening agents, but they also have lower melting points than known softening agents based on esterquats of ethanolamine.
- this unique combination of high hydrolytic stability and low melting points of the compositions allow for the formulation of stable super-concentrated and, if desired, anhydrous fabric softening formulations with or without the incorporation of stabilizing additives.
- super concentrated and anhydrous fabric softening formulations incorporating the composition of the invention are transparent in most instances.
- the present invention also encompasses the super concentrated fabric softening formulations comprising from 10 to 100 percent of the composition of the invention.
- These super concentrated formulations can be used for example, for a refill pack (to be diluted in a large bottle) or as concentrates for direct use by a consumer, or can help save transportation costs of the softener or the fabric or paper softening formulations.
- softergents Mixtures of fabric softeners and detergents (softergents) are commercially available. Such formulations can be in liquid, paste or granular form. Such softergents normally contain soft clays and/or cationic surfactants having only one long alkyl group in the molecule (for example, lauryltrimethyl ammonium chloride).
- Known softergents have a number of limitations. For example, the softening performance of these softergents is inferior to the performance of a fabric softener used separately in the last rinse of the wash process.
- Another limitation is the difficulty in formulating softergents containing cationic softener having more than one long alkyl chain in the molecule (common softening agent used in softening formulations).
- Still another limitation is the fact that a cationic softener having one or more ester links must be formulated at a low pH which does not correspond to typical neutral-to-alkaline pH of the detergent.
- compositions of the present invention due to the compatibility of compositions of the present invention with conventional detergent ingredients and because they are hydrolytically stable at typical detergent pH's they can conveniently be formulated with any known detergent ingredients into a softergent having none of the aforementioned limitations.
- the present invention concerns a powder or liquid softergent formulation comprising 1 to 90 weight percent of at least one composition of the invention, which softergent formulation has a pH in the range of from 1.5 to 12.
- the absence of solvent in the composition of the invention makes the softergent safer to use.
- the composition permits the selection of a softener which has a low enough melting point to be suitable for making powder softergent and allows optimum dispersion during the wash cycle.
- compositions of the present invention can suitably be formulated with a wide variety of known materials commonly found in fabric or paper softening formulations, laundry detergents, hard surface cleaning formulations and personal care formulations.
- materials used in fabric or paper softening formulations, laundry detergents, hard surface cleaning formulations and personal care formulations include, but are not limited to the following:
- Enzymes and Enzyme Stabilizers - Enzymes can be included for various fabric cleaning and fabric softening purposes.
- suitable enzymes include proteases, amylases, lipases, cellulases, and peroxidases, as well as mixtures thereof.
- the enzymes may be of any suitable origin, such as vegetable, animal, bactericidal, fungal and yeast origin.
- the enzymes used may be stabilized by the presence of water-soluble sources of calcium and/or magnesium ions in the finished compositions which provide such ions. Any water-soluble calcium or magnesium salt can be used as a source of calcium or magnesium ions.
- a wide range of useful enzyme and enzyme stabilizer materials are described in WO-A-95/19951 and WO-A-96/21715, and EP-A-0579295 and EP-A-0583536.
- Bleaching Agents and Bleach Activators Any known bleaching agent used in fabric or paper treatment applications can be used. Nonlimiting examples of suitable bleaching agents include oxygenated bleaches, percarboxylic acid bleaches, peroxygen bleaches and mixtures thereof. Bleach activator can also be used. Various nonlimiting examples of useful bleaching agents and bleach activators are given in WO- A-95/19951.
- Builders Inorganic and organic builders commonly used in fabric laundering formulations to assist in removal of paniculate solids can be used. Suitable builders include, but are not limited to, phosphates, polyphosphates, silicates, aluminosilicates, phosphonates, carboxylates, zeolites and succinates. Nonlimiting examples of suitable builders are described in WO-A-95/19951 and EP-A-0579295, and EP-A-0580245.
- Soil Release Agents Any known polymeric soil release agent used in laundry cleaning formulations can be used.
- Polymeric soil release agents include, but are not limited to, the compounds having: (i) at least one nonionic hydrophilic component consisting essentially of (a) polyoxyethylene segments with a degree of polymerization of at least 2, or (b) oxypropylene or polyoxypropylene segments with a degree of polymerization of from 2 to 10, or (c) a mixture of oxyalkylene units comprising oxyethylene and from 1 to 30 oxypropylene units, (d) cellulosic derivatives such as hydroxyether cellulosic polymers, (e) copolymeric blocks of terephthalate with polyethylene oxide or polypropylene oxide.
- Nonlimiting examples of useful soil release agents are given in WO-A-95/04802, WO-A-93/23510 and WO-A-
- Chelating agents Any known chelating agent is suitable for use. Suitable chelating agents include, but are not limited to, amino carboxylates, amino phosphonates, polyfunctionally-substituted aromatic chelating agents and mixtures thereof. It is believed that the benefit of the chelating materials is due in part to their exceptional ability to remove iron and manganese ions from washing solutions by formation of soluble chelates. Nonlimiting examples of suitable chelating agents are described in WO-A-95/19951 and WO-A-96/21715.
- Clay Soil Removal/Anti-Redeposition Agents Any water-soluble alkoxylated amines having clay soil removal and anti-redeposition properties normally used in granular or liquid detergents can be used. Nonlimiting examples of useful clay soil removal/anti-redeposition agents are described in WO-A-95/19951.
- Dispersing Agents - Suitable dispersing agents are polymeric dispersing agents such as, for example, polymeric polycarboxylates and polyethylene glycols, normally used in detergents. Nonlimiting examples of the dispersing agents are given in WO-A-95/19951. Protonated amines, such as those described in WO-A- 93/25648, and terephthalate/alkylene oxide copolymers, such as those described in WO-A-96/21715 can be used to enhance dispersion stability.
- Optical Brighteners Any known brightener used in detergents can be used. Suitable brighteners include, but are not limited to, derivatives of stilbene, pyrazoline, coumarin, and carboxylic acid. Nonlimiting examples of suitable brighteners are given in WO-A-95/19951 and WO-A-96/21715.
- Suds Suppressors Any known compound that suppresses or reduces the formation of suds is suitable for use. Such compounds include, but are not limited to, silicones, silica-silicone mixtures, monocarboxylic fatty acids and soluble salts thereof, high molecular weight hydrocarbons such as paraffin, and fatty acid esters of monoalcohols. These and other suitable suds suppressors are described in WO-A- 95/19951 and EP-A-0579295.
- Fabric Softeners Any known fabric softener compound can be used.
- suitable fabric softener compounds include clay softeners, conventional quaternary ammonium softening agents, anionic softeners, nonionic softeners, and cationic softeners. These and other suitable fabric softeners are described in WO-A-95/04802, WO-A-95/19951 , and WO-A-96/21715, and EP-A-0580245.
- (k) Detersive Surfactants Various surfactant materials such as anionic, nonionic, cationic, ampholytic, and zwitterionic surfactants can be used.
- suitable surfactant include linear alkyl sulfonates ("LAS"), C Montgomery- C 18 alkyl benzene sulfonates, primary and secondary branched-chain and random C 10 - C 20 alkyl sulfates ("AS”), and polyhydroxy fatty acid amide surfactants.
- liquid carriers such as, for example, water and C,-C 4 monohydric alcohols, thickening agents, viscosity control agents, di-(higher alkyl) cyclic amines, aqueous emulsions of predominantly linear polydialkyl or alkylaryl siloxanes absorbency enhancers, pH modifiers such as bases and acids, nonionic or other deflocculating agents, hydrotropes, colorants, perfumes, perfume carriers, preservatives, opacifiers, fluorescers, anti-shrinking agents, anti- wrinkle agents, anti-spotting agents, bactericides, germicides, fungicides, anti-corrosion agents, drape imparting agents, antistatic agents, ironing agents, wetting agents, strength additives such as carboxymethyl cellulose and water-soluble cationic polymers.
- liquid carriers such as, for example, water and C,-C 4 monohydric alcohols, thickening agents, viscosity control agents, di-(higher alkyl) cyclic
- PO propylene oxide
- MEA is monoethanolamine
- TEA is triethanolamine
- MDEA is methyldiethanolamine
- MAE is methyl amino ethanol (methyl monoethanolamine)
- DMAE dimethyl amino ethanol
- MDIPA is methyl diisopropanolamine
- TIPA is triisopropanolamine
- MeCI is methyl chloride Examples 1-2 Preparation of Polyalkanolamines with 2 Primary and 1 Secondary Hydroxyl Group
- polyalkanolamines with 2 primary and 1 secondary hydroxyl group is by reaction in a 1 :1 mole ratio of DEA with propylene- or butylene oxide to form [bis(2-hydroxyethyl)]-[2-hydroxypropyl]amine (DEA-1 PO) or [bis(2- hydroxyethyl)]-[2-hydroxybutyl]amine (DEA-1 BO).
- This reaction can be conveniently carried out by addition of the alkylene oxide to the DEA in a pressure vessel at temperatures from 50°C to 200°C, preferably from 80°C to 120°C and at a pressure of 1 to 80 bars.
- alkylene oxide is added at 110°C to DEA (1 :1 mole ratio) in a 2 liter vessel, the temperature being controlled by cooling the vessel and controlling the feed rate of the alkylene oxide. This reaction takes usually 2 to 3 hours to a point where the pressure becomes constant.
- the product thus obtained contains > 98 weight percent DEA-1 PO or DEA-1 BO and does not need further purification.
- An example to prepare polyalkanolamines with 1 primary and 2 secondary hydroxyl groups is by reaction in a 1 :2 mole ratio of MEA with propylene- or butylene oxide to form [(2-hydroxyethyl)]-[bis(2-hydroxypropyl)]amine (MEA-2PO) or [(2- hydroxyethyl)]-[bis(2-hydroxybutyl)]amine (MEA-2BO).
- This reaction can be conveniently carried out by addition of the alkylene oxide to the MEA in a pressure vessel at temperatures from 50°C to 200°C, preferably from 80°C to 120°C and at a pressure of 1 to 80 bars.
- alkylene oxide is added at 110°C to MEA (2:1 mole ratio) in a 2 liter vessel, the temperature being controlled by cooling the vessel and controlling the feed rate of the alkylene oxide. This reaction takes usually 2 to 3 hours to a point where the pressure becomes constant.
- the product obtained contains > 98 weight percent MEA-2PO or MEA-2BO and does not need further purification.
- An example to prepare polyalkanolamines with 1 primary and 1 secondary hydroxyl group is by reaction in a 1 :1 mole ratio of MAE (N-methyl-2-aminoethanol) with propylene- or butylene oxide to form N-methyl-(2-hydroxyethyl)-(2-hydroxypropyl) amine (MAE-1 PO) or N-methyl-(2-hydroxyethyl)-(2-hydroxybutyl)amine (MAE-1 BO).
- This reaction can be conveniently carried out by addition of the alkylene oxide to the MAE in a pressure vessel at temperatures from 50°C to 200°C, preferably from 80°C to 120°C and at a pressure of 1 to 80 bars.
- alkylene oxide is added at 110°C to MEA (2:1 mole ratio) in a 2-liter vessel, the temperature being controlled by cooling the vessel and controlling the feed rate of the alkylene oxide. This reaction takes usually 2 to 3 hours to a point where the pressure becomes constant.
- Polyalkanolamines having no primary hydroxyl groups can be prepared by standard methods known in the art. For example, these products can be made by reaction of ammonia or monoalkylamine with a C 3 or higher alkyleneoxide. In particular, ammonia can be reacted with propylene oxide to form TIPA and methylamine can be reacted with propyleneoxide to form MDIPA.
- polyalkanolamines prepared in Examples 1 to 8 can be esterified with a carboxylic acid or a carboxylic acid mixture of choice under conventional conditions, known to those skilled in the art.
- the polyalkanolamine is mixed with a carboxylic acid in the desired mole ratio in a vessel equipped with stirrer and a Dean-
- esters obtained were analyzed by GC, GPC or NMR for unreacted alkanolamine, mono-, di- and triester.
- the results, in percent by weight, are presented in Table I.
- the results show the effect of using PO vs. BO, of changing the particular carboxylic acid, of changing the mole ratio of carboxylic acid reacted, and the effect of using different combinations of primary and secondary alcohols, and using di vs. trialkanolamines.
- Examples 14, 15, 19 and 22 are comparative Examples which do not form a part of this invention but which were prepared according to the same procedure as the other Examples. These comparative examples demonstrate the manner in which the method of the present invention alters the resulting ester distribution.
- reaction mixtures prepared in the earlier examples were quatemized with dimethylsulfate (DMS), or methyl chloride (MeCI).
- DMS dimethylsulfate
- MeCI methyl chloride
- the percentage quatemized is reported in Table II.
- the quatemization is carried out according to conditions known to those skilled in the art. In general, it consists of heating the polyalkanolamine diester with DMS or MeCI with or without additional additives to lower the melting point, at 30°C -150°C, preferably at 75°C -95°C for 1 to 5 hours.
- compositions of the present invention tend to have lower melting points than the comparatives, which would aid in formulating the materials. Furthermore, the compositions of the present invention tend to be more hydrolytically stable, which is also advantageous, especially in liquid formulations.
- Several of the mixtures (with a pH of about 8.5) were kept for 2 weeks at a temperature of about 35°C. The percentage of product which was found to have hydrolyzed is reported in Table III. This data shows the general trend that the compositions of the present invention show improved hydrolytic stability over the comparative examples.
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99937527A EP1102833A1 (en) | 1998-07-30 | 1999-07-28 | Composition useful for softening, cleaning, and personal care applications |
AU52341/99A AU5234199A (en) | 1998-07-30 | 1999-07-28 | Composition useful for softening, cleaning, and personal care applications |
CA002338906A CA2338906A1 (en) | 1998-07-30 | 1999-07-28 | Composition useful for softening, cleaning, and personal care applications |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9816659.8 | 1998-07-30 | ||
GBGB9816659.8A GB9816659D0 (en) | 1998-07-30 | 1998-07-30 | Composition useful for softening, cleaning, and personal care applications and processes for the preparation thereof |
Publications (1)
Publication Number | Publication Date |
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WO2000006678A1 true WO2000006678A1 (en) | 2000-02-10 |
Family
ID=10836468
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1999/016981 WO2000006678A1 (en) | 1998-07-30 | 1999-07-28 | Composition useful for softening, cleaning, and personal care applications |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1102833A1 (en) |
AU (1) | AU5234199A (en) |
CA (1) | CA2338906A1 (en) |
GB (1) | GB9816659D0 (en) |
WO (1) | WO2000006678A1 (en) |
Cited By (22)
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WO2001032813A1 (en) * | 1999-11-01 | 2001-05-10 | Kao Corporation | Quaternary ammonium salt composition |
WO2007090567A1 (en) * | 2006-02-10 | 2007-08-16 | Unilever Plc | Fabric conditioning compositions |
WO2007092020A1 (en) * | 2006-02-10 | 2007-08-16 | Stepan Company | Fabric conditioning active compositions |
WO2011120822A1 (en) | 2010-04-01 | 2011-10-06 | Evonik Degussa Gmbh | Fabric softener active composition |
WO2011123284A1 (en) | 2010-04-01 | 2011-10-06 | The Procter & Gamble Company | Heat stable fabric softener |
WO2011123733A1 (en) | 2010-04-01 | 2011-10-06 | The Procter & Gamble Company | Heat stable fabric softener |
EP2497844A1 (en) * | 2011-03-10 | 2012-09-12 | Kao Corporation, S.A. | Quaternary ammonium esters (Esterquats) containing composition for inhibiting corrosion of metal surface |
US8361953B2 (en) | 2008-02-08 | 2013-01-29 | Evonik Goldschmidt Corporation | Rinse aid compositions with improved characteristics |
WO2013045565A1 (en) | 2011-09-28 | 2013-04-04 | Taminco | Aqueous liquids containing an organic compound and an n-(2-hydroxyalkyl) substituted n-alkylamine |
US8507425B2 (en) | 2010-06-29 | 2013-08-13 | Evonik Degussa Gmbh | Particulate fabric softener comprising ethylenediamine fatty acid amides and method of making |
US8563499B2 (en) | 2010-04-01 | 2013-10-22 | Evonik Degussa Gmbh | Fabric softener active composition |
WO2014092693A1 (en) * | 2012-12-11 | 2014-06-19 | Colgate-Palmolive Company | Esterquat composition having high triesterquat content |
WO2014092692A1 (en) * | 2012-12-11 | 2014-06-19 | Colgate-Palmolive Company | Esterquat composition having high triesterquat content |
JP2014523923A (en) * | 2011-07-28 | 2014-09-18 | アンガス ケミカル カンパニー | Amino alcohol compounds and their use as zero or low VOC additives for paints and coatings |
US8883713B2 (en) | 2012-01-30 | 2014-11-11 | Evonik Industries Ag | Fabric softener active composition |
US8883712B2 (en) | 2010-04-28 | 2014-11-11 | Evonik Degussa Gmbh | Fabric softening composition |
EP2899178A1 (en) * | 2014-01-23 | 2015-07-29 | Kao Corporation, S.A. | Anticaking compositions for solid fertilizers, comprising quaternary ester ammonium compounds |
US9441187B2 (en) | 2012-05-07 | 2016-09-13 | Evonik Degussa Gmbh | Fabric softener active composition and method for making it |
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US10011806B2 (en) | 2013-11-05 | 2018-07-03 | Evonik Degussa Gmbh | Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester |
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US8361953B2 (en) | 2008-02-08 | 2013-01-29 | Evonik Goldschmidt Corporation | Rinse aid compositions with improved characteristics |
WO2011123733A1 (en) | 2010-04-01 | 2011-10-06 | The Procter & Gamble Company | Heat stable fabric softener |
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JP2013525617A (en) * | 2010-04-01 | 2013-06-20 | ザ プロクター アンド ギャンブル カンパニー | Thermally stable softener |
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US10011806B2 (en) | 2013-11-05 | 2018-07-03 | Evonik Degussa Gmbh | Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester |
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Also Published As
Publication number | Publication date |
---|---|
CA2338906A1 (en) | 2000-02-10 |
EP1102833A1 (en) | 2001-05-30 |
AU5234199A (en) | 2000-02-21 |
GB9816659D0 (en) | 1998-09-30 |
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