MXPA98009180A - Composite of quaternary ammonium with high content of diester alquilico graso from trietanolam - Google Patents
Composite of quaternary ammonium with high content of diester alquilico graso from trietanolamInfo
- Publication number
- MXPA98009180A MXPA98009180A MXPA/A/1998/009180A MX9809180A MXPA98009180A MX PA98009180 A MXPA98009180 A MX PA98009180A MX 9809180 A MX9809180 A MX 9809180A MX PA98009180 A MXPA98009180 A MX PA98009180A
- Authority
- MX
- Mexico
- Prior art keywords
- further characterized
- quaternary ammonium
- mixture
- fatty acid
- weight
- Prior art date
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 title claims description 9
- 239000002131 composite material Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 163
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 31
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 23
- 239000004753 textile Substances 0.000 claims abstract description 10
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 53
- 239000000194 fatty acid Substances 0.000 claims description 53
- 150000004665 fatty acids Chemical class 0.000 claims description 51
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 27
- -1 -phosphates Chemical class 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000011780 sodium chloride Substances 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000004744 fabric Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 239000011630 iodine Substances 0.000 claims description 12
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 229940027983 antiseptics and disinfectants Quaternary ammonium compounds Drugs 0.000 claims description 9
- 239000002168 alkylating agent Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 240000002791 Brassica napus Species 0.000 claims description 5
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 5
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 5
- 235000010469 Glycine max Nutrition 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 235000014121 butter Nutrition 0.000 claims description 5
- 238000005956 quaternization reaction Methods 0.000 claims description 5
- 239000003760 tallow Substances 0.000 claims description 5
- 240000007842 Glycine max Species 0.000 claims description 4
- 210000003491 Skin Anatomy 0.000 claims description 4
- 239000011833 salt mixture Substances 0.000 claims description 4
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-Amino-2-propanol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 3
- NEHMKBQYUWJMIP-UHFFFAOYSA-N Chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N Dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 3
- 229940102253 ISOPROPANOLAMINE Drugs 0.000 claims description 3
- 229940050176 Methyl Chloride Drugs 0.000 claims description 3
- 229940073608 benzyl chloride Drugs 0.000 claims description 3
- 230000003750 conditioning Effects 0.000 claims description 3
- 238000009499 grossing Methods 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 210000002374 Sebum Anatomy 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 150000003626 triacylglycerols Chemical class 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 3
- DENRZWYUOJLTMF-UHFFFAOYSA-N Diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims 2
- WVLBCYQITXONBZ-UHFFFAOYSA-N Trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 claims 2
- 229940008406 diethyl sulfate Drugs 0.000 claims 2
- 230000003373 anti-fouling Effects 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 1
- 239000000314 lubricant Substances 0.000 claims 1
- 230000001050 lubricating Effects 0.000 claims 1
- 239000000700 tracer Substances 0.000 claims 1
- 239000004902 Softening Agent Substances 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 150000003863 ammonium salts Chemical class 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 239000000463 material Substances 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 19
- JNYAEWCLZODPBN-CTQIIAAMSA-N Sorbitan Chemical compound OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- 239000003093 cationic surfactant Substances 0.000 description 13
- 239000006185 dispersion Substances 0.000 description 13
- 239000002689 soil Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 239000002736 nonionic surfactant Substances 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- 238000007792 addition Methods 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 239000003607 modifier Substances 0.000 description 10
- 238000005886 esterification reaction Methods 0.000 description 9
- 125000002091 cationic group Chemical group 0.000 description 8
- 239000003205 fragrance Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000008247 solid mixture Substances 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 230000036961 partial Effects 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- MMINFSMURORWKH-UHFFFAOYSA-N 3,6-dioxabicyclo[6.2.2]dodeca-1(10),8,11-triene-2,7-dione Chemical group O=C1OCCOC(=O)C2=CC=C1C=C2 MMINFSMURORWKH-UHFFFAOYSA-N 0.000 description 5
- GQZXNSPRSGFJLY-UHFFFAOYSA-N Hypophosphorous acid Chemical compound OP=O GQZXNSPRSGFJLY-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 235000019645 odor Nutrition 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000600 sorbitol Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 229940100198 ALKYLATING AGENTS Drugs 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
- 239000004698 Polyethylene (PE) Chemical group 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 230000000111 anti-oxidant Effects 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 4
- 150000002314 glycerols Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000004669 nonionic softener Substances 0.000 description 4
- 229920000223 polyglycerol Chemical class 0.000 description 4
- 239000003638 reducing agent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N Behenic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 3
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 3
- SEQDDYPDSLOBDC-UHFFFAOYSA-N Temazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 SEQDDYPDSLOBDC-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 230000000844 anti-bacterial Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- 238000006065 biodegradation reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 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
- 238000004040 coloring Methods 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000002979 fabric softener Substances 0.000 description 3
- 125000001924 fatty-acyl group Chemical group 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000573 polyethylene Chemical group 0.000 description 3
- 150000003138 primary alcohols Chemical class 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 239000004034 viscosity adjusting agent Substances 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N 3-(2,3-dihydroxypropoxy)propane-1,2-diol Chemical class OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- OKOBUGCCXMIKDM-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)-N-[6-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoylamino]hexyl]propanamide Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NCCCCCCNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 OKOBUGCCXMIKDM-UHFFFAOYSA-N 0.000 description 2
- JEHDNEGUWVKRSU-UHFFFAOYSA-N 4-tridecylphenol Chemical compound CCCCCCCCCCCCCC1=CC=C(O)C=C1 JEHDNEGUWVKRSU-UHFFFAOYSA-N 0.000 description 2
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N Butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
- 240000005497 Cyamopsis tetragonoloba Species 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N Gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M Lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L MgCl2 Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229940075579 Propyl Gallate Drugs 0.000 description 2
- CXQXSVUQTKDNFP-UHFFFAOYSA-N Simethicone Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N TBHQ Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- IYFATESGLOUGBX-NDUCAMMLSA-N [2-[(2R,3R,4S)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-NDUCAMMLSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000005466 alkylenyl group Chemical group 0.000 description 2
- 230000003078 antioxidant Effects 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium monoxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N edta Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000005313 fatty acid group Chemical group 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- 230000000670 limiting Effects 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000002829 nitrogen Chemical group 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 230000002335 preservative Effects 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N propyl 3,4,5-trihydroxybenzoate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 239000000473 propyl gallate Substances 0.000 description 2
- 235000010388 propyl gallate Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2R,3R,4S,5R,6S)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2R,3R,4S,5R,6R)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SEVPGNFKEDEULZ-UHFFFAOYSA-M 1-pyridin-1-ium-1-ylethanone;chloride Chemical group [Cl-].CC(=O)[N+]1=CC=CC=C1 SEVPGNFKEDEULZ-UHFFFAOYSA-M 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N 2-Imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- MQRCHVBRBGNZGJ-UHFFFAOYSA-N 2-[3,5-bis[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethyl]-2,4,6-trioxo-1,3,5-triazinan-1-yl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCN2C(N(CCOC(=O)CCC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CCOC(=O)CCC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 MQRCHVBRBGNZGJ-UHFFFAOYSA-N 0.000 description 1
- VUKAUDKDFVSVFT-UHFFFAOYSA-N 2-[6-[4,5-bis(2-hydroxypropoxy)-2-(2-hydroxypropoxymethyl)-6-methoxyoxan-3-yl]oxy-4,5-dimethoxy-2-(methoxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)-5-methoxyoxane-3,4-diol Chemical compound COC1C(OC)C(OC2C(C(O)C(OC)C(CO)O2)O)C(COC)OC1OC1C(COCC(C)O)OC(OC)C(OCC(C)O)C1OCC(C)O VUKAUDKDFVSVFT-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
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Abstract
The present invention relates generally to a textile softening composition comprising, as a softening agent, a quaternary ammonium salt comprising a mixture of mono-, di- and tri-ester components, wherein the amount of diester quaternary is more than about 55% by weight and the quaternary amount of the triester is less than 25% by weight, based on the total amount of the ammonium salt, the invention also relates to a process for preparing said agent to soften
Description
COMPOSITE OF QUATERNARY AMMONIUM WITH HIGH CONTENT OF DIESTER ALQUILICQ GRASO FROM TRIETANOLAMI A
FIELD OF THE INVENTION
The present invention relates generally to an improved softening composition containing quaternary ammonium compounds having a high content of diester and low triester content and a process for preparing the same.
BACKGROUND OF THE INVENTION
The present invention relates to a softening composition! based on quaternized ester containing high content of diester and low content of triester. Compositions of this type have unexpectedly demonstrated superior softening performance and stability compared to the prior art compositions. Fabric softener compositions suitable for providing fabric softening and static control benefits during laundry are well known in the art. Such compositions generally contain softener as a component. quaternary ammonium compounds substantially insoluble in water having two long alkyl chains.
In addition, the use of several quaternized ester-amines as fabric softening agents is also well known in the art. The patent of E.U.A. No. 4.339.39I of Hoff annr et al. Per example describes a series of quaternized ester-amines having co-utility or fabric softeners. The patent of E.U.A. No. 5,286,622 describes ester quaternized amines having cloth softening and hydrophilicization properties which are obtained by the reaction of unsaturated fatty acids containing at least 40% mol. Of double bonds transfused or esters thereof with alcanala inas and the subsequent quaternization of the reaction products with the alkylating agents. XO / 93/21291 of Henkel claims rights for textile treatment agents which contains, as a softener, quaternary ammonium compounds with groups 1-. 2- or 3-acyloxyalkyl linked to the nitrogen atom. The compounds are said to have low viscosity if all or some of the acyl groups are derived from unsaturated fatty acids with at least 307. in the cis form. The patent of E.U.A. No. 5,02,033 of KAO discloses a softening composition comprising at least one quaternary ammonium salt of the following formulas-
wherein each of R1 and Rz represents a hydrocarbon radical having 12-22 carbon atoms preferably 16-22 carbon atoms and an unsaturated bond. R3 and * represent an ethyl or
(CHa-CH0) "NH where n is an integer from l to 5 and Y is H or methyl? each of Rβ and R * represents a hydrocarbon radical having 11-21 carbon atoms and an unsaturated bond? X represents halogen C .-. H.jSO ,,.? wherein the stereoisomeric structure if said above salt includes both the cis-ion and the trans-somer being in the range of the 6-isomer to the trans-isomer in the range of 25/75 to 90/10. The patent of E.U.A. No. 4,767,547 discloses fabric softening compositions containing a rapidly biodegradable quaternary amino softening agent of the formul¬
in which? 0 0 0 II II II Q is -a-c or C-O or o-c-a R ^ is (CH2) "- Q ~ T ^ o Ta or R3? R--, is Ct-C alkyl? Ttr Ta T ... 7 T ^. Ta are (same or different) alkyl or alkenyl of C ^ -Cj,;,. n is an integer from 1 to 4? and X ~ is an anion compatible with the softener having the composition having a pH of 20 ° Cr of 2.5 to 4.2 after dilution in deionized water at a concentration of 0.5% to 17. of said rapidly biodegradable quaternary ammonium compound. WO 94/20597 by Procter & Gamble refers to softening compounds containing diester quaternary ammonium compounds in which the fatty acyl groups have an iodine value of more than approximately 5 to less than about 10 a weight ratio of the 6-isomer to the trane-isomer of base approximately 30/70 when the iodine value is less than about 25 r, the level of unsaturation being less than about 5% in weight where said compounds are capable of forming concentrated aqueous compositions with contractions greater than about. 13% by weight at an iodine value of more than about 10 without modifiers of viscosity different from the normal polar organic solvents r present in the starting material of the added compound or electrolyte. EP 0 550 361 to Stepan discloses cationic compositions for treating fabrics comprising quaternary ammonium compounds which are the reaction product of a long chain fatty acid and a tertiary amine wherein the ratio of the fatty acid to the amine is from 1.T5 and 1.4. W0 91/01295 to Henkel discloses useful quaternary ammonium compounds or textile treatment agents? which are prepared by reacting fatty acids with alkanolamine and then renting them to give the quaternary compounds. The esterification reaction is carried out in the presence of an acid catalyst such as hypophosphorous acid. The final product comprises "allegedly" mono-r di-r and triester components in a ratio of 10-62-28%, but there is no publication of a process for the preparation of a final product having a high diester content. That is to say »of mass approximately 557% by weight» and low content of »tries» that is to say »of menoß of approximately 20% by weight. Finally »WO 94/14935 to Henkel discloses concentrated textile softening dispersions containing quaternary amino compounds derived from triethanolamine containing» 1 »2 or 3 fatty acyl loxieti groups. When the proportion of compounds having two fatty acyloxyethyl groups is greater than 50% by mol, these compounds have allegedly a particularly low viscosity. However, no method was disclosed in this document to achieve this level of diester and gives an indication of the triéeter content of the final product. It is therefore evident that the prior art considered hereinabove does not contemplate or suggest the quaternized diester-based softening composition containing high diester content and low trieeter content. A process for the preparation of such products is also not contemplated. According to the above »it is an object of the present invention to provide a quaternized diester product having high diester content and low triester content. It is a further object of the present invention to provide a fabric softening composition comprising as a main ingredient the quaternary diester compound of the present invention. Another object of the present invention is to provide the fabric softening composition that has been given in yellowish and have improved softening performance and textile softening properties such as improved biodegradability, viscosity, water absorbency, stability, and the like. These and other objects are immediately apparent with the following description.
BRIEF DESCRIPTION OF THE INVENTION
The present invention relates generally to a textile softening composition comprising as a "softening agent" a mixture of quaternary ammonium salts comprising a mixture of mono- »di- and tri-ester components» wherein the amount of the The diester quaternary is more than 55% by weight and the quaternary amount of the triester is less than 20% by weight »with bae in the total amount of quaternary ammonium, The invention also relates to a method for preparing said softening agent.
?
Figure 1 shows the viscosity as a function of the temperature of the product. Figure 2 shows the viscosity profile as a function of time at different temperatures.
P? R U GIP PET P PE A IN TION
The present invention relates generally to a fabric softening composition comprising a quaternary ammonium-based softening agent that is high in diester and low in triester content and to a process for the preparation thereof. The quaternary ammonium compounds having particularly good yield and stability profiles are obtained by the reaction of fatty acids of -C-C. ^ Or the products of their oxidation o or a mixture of such acids con with an alkanolamine in the presence of an acid catalyst »where the fatty acid ratio of alkanolamine is 1.60-1-80. The resulting ester reaction products are subsequently quaternized to obtain the quaternary amine salts of the present invention. Preferably the fatty acid is a t-t-Caa acid containing a degree of unsaturation such that the iodine value ("VI") in the range of 20-90"preferably" of 40-60"and more preferably still »in a range of 45-55. Preferred fatty acids include but are not limited to the same »oleic» palmitic »erucidic» eicosanic and mixtures thereof. Soybeans »the bait» the palm and the palm kernel »and rapeseed» the butter mixtures thereof and the like are typical sources for the fatty acid that can be employed in the present invention. Partial hydrogenation can be used "if required" to minimize the levels
pol i insa ured in order to improve the stability of the final product. It is also preferred that the fatty acids employed in the present process having a ratio of 6-isomer to trans-isomer of 80? 20 to 95-5. More preferably, the trans-isomer content of said fatty acids is less
of 10%. An optimal trans-isomer content is between 0.5 and 9.9%. The most preferred fatty acid is a mixture of bait and distillate bait having a cis? trans of more than 9.1. The alkanola inae employed in the present invention
correspond generally to the formula-
R_ »I R-, - N-R" 5 wherein R3 »Rx and Rz are independently selected from hydroxyalkyl groups of Preferred alkanol amines include but are not limited thereto» treiethanolamine »propanoldiethanolamine» ethanoldi isopropanolamine »triisoprapa nola and mixtures thereof Triethanolamine is the most preferred alkanolamine The molar ratio of the fatty acid to the alkanolamine is in the range of 1.65-1.80"and more preferably" in the range of 1.65-1.75. The best results when the molar ratio is 1.70 The acid catalyst employed in the present process includes but is not limited to sulfonic acid phosphorous acid p-toluene sulphonic acid methanesulfonic acid »oxalic acid» hypophosphagous acid and an acceptable Lewis acid A preferred acid catalyst is hypophosphorous acid, 0.02-0.2% by weight is typically used in the present process. more preferably 0.1 to 0.15% by weight of the acid catalyst »based on the weight of the fatty acid. The esterification of fatty acids with alkanolamines is carried out at once. temperature of 160 ° -310 ° C until the reaction product has an acid value of less than 5. In addition »the formation of triester in the final product can be minimized» by continuing the heating regime to form the ether mixture. to ina. A heating rate of 0.8 ° -3 ° C / minute »preferably of 1.25 ° C ~ 3 ° C» from a temperature of 70 ° C to a temperature in a range of 170 ° C to 210 ° C is effective to minimize the formation of triester. After esterification, the crude product is reacted with alkylating agents in order to obtain the quaternary ammonium product. Preferred alkylating agents include straight or branched chain alkyl or straight-branched alkyl-halophosphides »-phosphates» -carbonates of Cj-C., »Alkyl-halides» -phosphates or -sulfates »of C7-Cle >; »And mixtures thereof. Some examples of the preferred alkylating agents include but are not limited to the same »methyl chloride» benzyl chloride »ethyl sulfate» dimethyl carbonate »dimethyl phosphate» dimethyl sulfate or mixtures thereof. The choice of the type and amount of the alkylation agent employed is completely within the skill of someone in the art. Typically, when the dimethyl sulfate is an alkylating agent, from 0.7 to 1.0 moles of dimethyl sulfate per mole of ester is satisfactory to produce the quaternized product. Quaternization in bulk or solvent can be carried out at temperatures ranging from 60 ° to 120 ° C. If solvent is used, then the starting materials and / or the product must be soluble in the soluble to the extent necessary for the reaction. Solvents of this type are generally known in the art. Suitable examples include the polar solvent such as, for example, lower alcohols, that is, C1-CA alcohols. Other solvents that can be used include but are not limited to mono-> di- and tri-glycerides »fatty acid» glycol and mixtures thereof. A resulting mixture of quaternary ammonium salts comprises a mixture of mana- (I) »di- (II) and triester (III) components of the following formulas-
(I) R-C-0-HßC-HzC + CHaCHß0H \ / X- N / \ H0-H2C-HaC CH,
0
-C-O-H ^ C-Ha + CHaCH ^ OH (II) \ / X- N / \
0
RC-0-H ^ CH-.C + CHa-CHa.-0-CR (III) / x- N / \ RCO-Ha-C-HaC CH-, where R represents a hydrocarbon radical having 12- 22 carbon atoms »preferably 16-22 carbon atoms having a total VY in the range of 20-90» preferably 40-60 »and more preferably 45-55» and > It represents an anion compatible with the fabric softener that includes but is not limited to the halogen, CH3S0, or CaHsS0. The reaction products may also contain quaternary amounts of methyl trialkanal ina and other impurities. Further »the amount of diester in the final product is more than 557% by weight and the amount of triester less than 25%» preferably less than 20% by weight »based on the total amount of the ammonium salt product quaternary. The typical composition of the product contains 60-65% by weight of diester and less than 18% by weight of triester »more preferably less than 15% by weight of triester. Furthermore, the ratio of the cis to trans double bonds of the above salts is preferably in the range of 80 [deg.] 20 to 95 [deg.]. In the most preferred embodiment, the amount of trans-isomer is less than 10% and ideally is in the range of 5 to 9.5%. There are several convenient methods to obtain the cis relationship? desired trans of the quaternary ammonium salt product. The preferred method for producing the mixture of quaternary ammonium salts from cis-isomeric and trans-isomeric fatty acids after adjusting said acids to the desired ratio. Another method is to produce the mixture of ammonium salts, quaternary from the mixture after adjusting the ratio of the same »isomerizing a portion of the fatty acid - cis-isomeric or ester thereof to the transesome» in the presence of a metallic catalyst. Other methods are immediately apparent to the skill "and completely within it" of someone with ordinary skill in the art. The fabric softening composition of the present invention having high diester content and low triester content demonstrates superior performance as compared to the typical ester-amine quaternary compounds and the excellent color and odor stability allows the formulator greater freedom in the Preparation of high quality softener products. The compositions may be aqueous, preferably concentrated, liquids containing from 3 to 50%, preferably from 10 to 45% and more preferably from 15 to 40% by weight of the quaternary ammonium compound of the present invention. The compositions of the present invention can be further concentrated as solids in the form of particles containing from 50 to 95% »preferably from 60 to 90% of the quaternary ammonium softening composition» if desired. Water can be added to the solid compositions in the form of particles to form liquid fabric softening compositions either dilute or concentrated according to the invention. The solid composition in the form of particles can also be added directly to the rinse bath in order to provide a suitable use concentration »which is typically in the range of 10 to 1000 ppm» more preferably in a range of 50. at 500 ppm. The quaternary ammonium compounds according to the present invention can be prepared generally by reacting at least one CX? ~ Crtst fatty acid having a VY of 20 to 90 with an alkanolamine in the presence of an acid catalyst. The ratio of the alamin acid is in the range of 1.6 to 1.8 and the reaction is carried out at a temperature of 175 ° C to 210 ° C until the reaction product has an acid value below 5. heating regime from 0.8 ° C to 3.0 ° C per minute in order to minimize the formation of triester. The products are subsequently rented of esterification in order to obtain the quaternary ammonium product. A normal softening composition for rinse cycle according to the present invention can be prepared by heating water previously at a temperature of 45 ° to 60 ° C in a suitable vessel and acidifying it to a pH of 2.7 to 3.2. The heated quaternary ammonium salt is then added to the acidified water with stirring while maintaining the temperature at 45 ° C-60 ° C. Fragrance and other optional ingredients can then be solubilized to the softening arrangement and the weight is then adjusted with deionized water. Dispersions such as this are typically stable in storage within a temperature range of 4 ° C to 50 ° C. The quaternary ammonium salt mixtures of the present invention can also be used in products other than fabric softening compositions. These products can include hair care formulations »skin care formulations and the like» by the softening »lubrication» softening and the condition of said hair and / or skin when applied in effective amounts. These and other uses will be immediately apparent to one of ordinary skill in the art. Although the stability of the fabric softening composition of the present invention is such that no surfactant co-surfactants are required, these may nevertheless be included together with a wide variety of other optional ingredients. A brief limiting description of some of the optional ingredients that may be employed in the textile softening compositions of the present invention is provided below.
I.) Viscosity / Dispersability Auxiliary Materials As previously mentioned, the relatively concentrated compositions of the quaternary steres of the present invention can be prepared so that they are stable without the addition of concentration aids. Furthermore, the compositions of the present invention may require organic and / or inorganic concentrating auxiliaries to achieve even higher concentrations and / or to satisfy higher stability standards depending on the other ingredients. These auxiliary concentration materials which are typically viscosity modifiers may be needed or preferred to "ensure stability under extreme conditions" when particular active softener levels are present in the reaction to the VY.
Surfactant Assistive Materials Surfactant Assistive Materials typically fall into four categories- (1) cationic surfactants such as long chain alkyl. (2) nonionic surfactants; (3) amine oxides »and (4) fatty acids. It is also possible, of course, to use mixtures of the aforementioned auxiliary surfactant concentrates.
(1) Cationic surfactants nona alkyl chain laccase Cationic surfactant agents soluble in water long chain alkyl or ester which are preferred fall generally within the following general formula -
[R «| \ | < < R3) 3 > (~
wherein the group R2 is a Cß-Caa hydrocarbon group, preferably C ?a-Clβ alkyl group or the corresponding ester interrupted linking group with a short chain alkylene group (0, - C *) between the ester bond and N »and having a similar hydrocarbon group. Each R is an alkyl unsubstituted or substituted for C ^ - ^, (for example by hydroxy) or hydrogen, preferably methyl, and the counter anion) < an anion compatible with the softener such as "chlorine bromide" methyl sulfate "etc. The cationic surfactants "if present" are usually added to the solid compositions at a level from 0% to about 157% by weight, preferably from about 3% to about 15%, more preferably from about 57%. imadamente 15%. In liquid compositions, they are usually employed at a level from 0% to approximately 15%, preferably from about 0.5% to about 10%. In general, the total amount of single long chain cationic surfactant is added in an amount effective to obtain a stable composition.
The resulting levels represent the activity of the single long chain alkyl cationic surfactant agent which is added to the composition of the present invention. The ranges do not include the amount of monoester which is already present in the quaternary ammonium compound of diester. The long chain group Rz of the single long chain alkyl cationic surfactant generally contains a group having the about 10 to about 22 carbon atoms, preferably about 12 to about 16 carbon atoms for the solid compositions, and preferably about 12 to about 18 carbon atoms for the liquid compositions. This group Ra can be attached to the cationic nitrogen atom behind a group containing one or more ester, amide, ether, amine, etc., linking groups. preferably ester, which may be desirable for their hydrophilicity, biodegradability, etc. increased. Such linking groups are preferably within about 3 carbon atoms of the nitrogen atom. In the patent of E.U.A. No. 4,840,738, which is incorporated herein by reference, are disclosed to suitable biodegradable single long chain alkyl cationic surfactants. If the corresponding non-quaternary amines »any acid (preferably a mineral or polycarboxylic acid) which is added to keep the ester groups stable will also keep the amine catalyzed in the compositions and preferably during the rinsing» so that the amine has a cationic group . The pH composition is regulated (pH from about 2 to about 5, preferably from about 2 to about 4) to maintain an appropriate and effective loading density in the aqueous liquid concentrate and then in higher dilution, eg to form a less product. concentrate and / or after the addition to the rinse cycle of a laundry washing process. The main function of the water-soluble cationic surfactant is to decrease the viscosity and / or increase the dispersibility of the diester softener and it is therefore not essential that the cationic surfactant itself has substantial softening properties, although this may be the case . Also, the surfactants having only a single long chain alkyl, presumably because they have a higher solubility in water, can protect the diester softener so that they do not interfere with the anionic surfactants and / or detergency builders and are transferred to the rinse. Other cationic materials with ring structures such as alkyl imidazoline »imidazolinium» pyridine and pyridinium salts having a single alkyl chain of Ci St-C3ct can also be used. A very low pH is required to stabilize »for example the ring structures of imidazoline. Some alkyl imidazolinium ealees useful in the present invention have the general formula?
wherein Y * is -C (0) -0- »-0- (0) C-» -C (0) -N (Rβ) »or -N (Rβ) -C < 0 > - in which R89 is hydrogen or an alkyl radical of Cx-C ^ RA is an alkyl radical of Ct-C ^? each of R "7- and R * are independently selected from R and R * as defined herein above for a single long chain cationic surfactant with only one R *. Some salts of alkyl pyridinium useful in the present invention They have the general formula-
where R * and X ~ are as defined above. A typical material of this type is acetyl pyridinium chloride.
(2) Alkoxylated nonionic surfactants Nonionic surfactants suitable as viscosity / dispereability modifiers include the addition products of ethylene and / or propylene oxide with fatty alcohols, fatty acids, fatty amines, etc. Any of the alkoxylated materials that are described < hereinafter as a nonionic surfactant. In general terms, the nonionic surfactants herein can be used solid compositions at a level of from about 5% to about 20%, preferably from about 87% to about 15%, under liquid conditions at a level from 07. Approximately 5% »preferably from about 0.17. to about 5% »more preferably about 0.27. at about 37. Suitable nonionic water-soluble surfactants generally fall within the scope of the following general formula?
wherein Ra "for both solid and liquid compositions" is selected from the group consisting of two alkenyl hydrocarbon groups. The primary and secondary chain and branched chains and the substituted phenolic hydrocarbon groups can be secondary and branched primary chain alkyl and alkenyl? said hydrocarbyl groups having a hydrocarbon chain length of from about 8 to about 20 preferably from about 10 to about 18 atoms; carbon. More preferably, the chain length of the hydrocarbyl to the liquid compositions is from about 16 to about 18 atoms and for the solid compositions they form from about 10 to about 14 carbon atoms. Of the general formula for the ethoxylated nonionic surfactants of the present »Y is typically -0-» ~ C (0) - »~ C (0) N < R) - »or -C (0> N (R) R-» where R »when present» have meanings given hereinabove »and / or R can be hydrogen» and z is at least about 8 » preferably at least about 10-11.The yield and usually the stability of the softening composition decreases when less ethoxylate group is present. The nonionic surfactants herein are characterized by a BHL (hydrophilic-hypophysis balance). 1) from about 7 to about 20, preferably from about 8 to about 15. By defining Ra and the number of ethoxylate groups, the BHL of the surfactant is mostly determined, however it is preferred that for liquid compositions "concentrated" the ionic surfactants contain relatively long-chain Rz groups and are relatively high-grade ethoxy, although the shorter-chain alkyl surfactants have In short ethoxylated groups can proceed BHL required »are not as effective. Nonionic surfactants are preferred as viscosity / dispersion viscosity modifiers in the other modifiers disclosed herein with compositions with higher levels of perfume. The nonionic surfactants employed in the present invention include but are not limited to the following examples. In the examples »the number of ethoxy groups in the molecule (EO) is defined by a whole number.
(1) Straight-chain primary alcohol alkoxylates The deca- »undeca-» dodeca- »tetradeca-» and pentadeca-ethoxylates of n-hexadecanol »and n-octadecanol having a BHL within the preferred range are useful as modifiers of viscosity / dispersibility of the context of this invention. Preferred examples of ethoxylated primary alcohols useful herein as viscosity / dispersion viscosity modifiers of the compositions include but are not limited thereto, n-ClßE0 (10> and n-CloE0 (ll). The ethoxylates of mixed natural or synthetic alcohols in the chain length range of the
"eebo" are also useful in the present. Some specific examples of such materials include tallow alcohol-E0 (11) »tallow alcohol-E0 (18)» and sebum alochol-E0 < 25).
(2) Secondary straight-chain alcohol alcoxylates The deca- »undeca-» dodeca- »tetradeca-» pentadeca- »actadeca-» and nonadeca-ethoxylates of 3-hexadecanol »2-octadecanal» 4-eicosanol and 5- eicosanol "having a BHL within the preferred range are viscosity / dispersibility modifiers useful in the context of the present invention. Some examples of ethoxylated secondary alcohols useful herein as viscosity / dispereability modifiers of the compositions include but are not limited thereto? 2 ~ Cl < s, E0 (11.)? 2-CaOE-0 (11)? and 2 ~ C1 < fcE0.14 > ,.
(3) Alkyl phenol alkoxylates As in the case of the alcohol alkoxylates »the hexade octadeca-ethoxylates of alkylated phenols» particularly monohydric alkyl phenols »having a BHL within the preferred range are useful as viscosity / dispersibility modifiers. Hexa- »tra octadeca-ethoxy lates of p-tridecyl phenol» m-pentadeci Ifenol »and eimilaree are useful herein. Preferred examples of ethoxylated alkylphenols useful as viscosity / dispersibility modifiers include but are not limited thereto? p-tridecylphenol E0 < 11) and p-pentadeci Ifenol E0 (18). One of ordinary skill in the art that a phenol group in the non-ionic formula is the equivalent of an alkylene group containing 2 to 4 carbon atoms. For the present purposes, the nonionic surfactants containing a phenylene group are considered to contain an equivalent number of carbon atoms calculated as the sum of the carbon atoms in the alkyl group plus about 3.3 carbon atoms for each phenylene group.
(4) Olefinic Alkoxylates The alkenyl alcohols "both primary and secondary" and the alkanyl phenols corresponding to the aforementioned ones hereinbefore can be ethoxylated with BHL within the range mentioned herein and used as iscasity modifiers. dispersibility in the compositions of the present invention.
< 5 > Branched chain alkoxylates The branched chain primary and secondary alcohols which are obtainable by the well known "0X0" process can be ethoxylated and used as viscoeity / die-dispersity modifiers in the present compositions. The ethoxylated nonionic surfactants summarized hereinabove can be usefully employed in the present compositions either alone or in specific mixtures.
< ?? Oxides 4 * ñj Suitable amine oxides those with an alkyl or hydraxyalkyl moiety of about 8 to about 28 carbon atoms "preferably from about 8 to about 16 carbon atoms" and two alkyl portions selected from the group consisting of alkyl groups and hydroxyalkyl groups with about 1 to about 3 carbon atoms. The oxides of aarin if used are generally present in solid compositions at a level from 0% to about 15%, preferably from about 37. to about 157.? and in co poei ionee liquids at a level from 07. to approximately 5% »preferably from about 0.25% to about 2%. The total amount of amine oxide is generally present in an amount effective to provide a stable composition. Preferred examples of amine oxides and leables in the present invention include but are not limited thereto »dimethyloctone oxide» laminate »diethylene oxide laminate» bis- (2-hydroxyethyl) dodecylamine oxide »oxide of ethylethyl-hexadecylamina »dimethyl oxide l-2-hydroxyoctadeci lamina and coconut fatty alkyl dimethylamine oxide.
< 4) ftcidps griffqff Suitable fatty acids include those which are approximately 12 to about 25% by weight, preferably about 13 to 22% more preferably from about 16 to about 20% total carbon atoms, containing the fatty portion of the fatty acid. 10 to about 22, preferably from about 10 to about 18, more preferably from about 10 to about 14 carbon atoms. The shortest portion contains from about 1 to about 4, preferably from about 1 to about 2 carbon atoms. The fatty acids are typically present at approximately the levels described above for the amine oxides. Fatty acids are preferred auxiliary concentrates for those compositions that require an oxidizable concentration and permeation-containing material.
Auxiliary electrolyte concentration materials Inorganic agents for viscosity control which can also act as surfactant concentration aids »increase their effect» include ionizable salts »soluble in water. Such salts are also optionally incorporated into the compositions of the present invention. An extensive variety of ionizable salts can be used. Examples of suitable salts include, but are not limited to, the halides of the metals of groups IA and HA of the periodic table of elements, for example, calcium chloride, magnesium chloride, sodium chloride, bromide. potassium and lithium chloride. The ionizable salts are particularly useful during the process of mixing the ingredients to make the compositions herein and to obtain the desired viscosity. The amount of ionizable salts used depends on the amount of active ingredients used in the compositions.
Typical levels of the salts used to confirm the viscosity of the composition are approximately 20 to about 20,000 parts per million (ppm), preferably from about 20 to about 11,000 ppm, by weight of the composition. The alkylene polyamide salts can be incorporated into the composition to give viscosity control in addition to and instead of the water soluble ionizable salts described above. Additionally, "these agents can act as scavengers" by forming ion pairs with the anionic detergent moved from the main wash to the rinse and can improve the smoothing performance. These agents can stabilize the viscosity over a wider temperature range especially at low temperatures as compared to inorganic electrolytes. Some specific examples of alkylene polyammonium salts include but are not limited to l-linole ponoclor idrate and 1-5-diammonium-2-methyl pentane dihydrochloride.
H Eg PJligfrtforftg Stabilizers may also be optionally employed in the compositions of the present invention.
The term "stabilizer" as used herein includes antioxy before and reducing agents. These agents are typically present at levels from 07. to about 27. "preferably from about 0.01% to about 0.2%", more preferably from about 0.05% to about 0.17. for antioxidants and more preferably from about 0.01% to about 0.2% to reducing agents. The use of stabilizers ensures good odor stability in storage conditions of long duration. Furthermore, the use of antioxidants and stabilizers of reducing agents is especially critical for fragrance-free or low-fragrance products. Some examples of antioxidants that can be employed in the compositions of the present invention include, but are not limited to. the same »a mixture of ascorbic acid» ascorbic palmitate »propyl gallate» obtainable from Eastman Chemical Products »Inc.» under the trade name Tenox® PG and Tenox Sl »a mixture of HTB. butylated hydroxy toluene)» HAB (butylated hydroxyanisole) »propyl gallate and citric acid» obtainable from Eastman Chemical Products »Inc . »With the factory name Tensx-6? hydroxy toluene buty side »available from UOP Process Division with the name of Sustane" BHT? but i Tertiary Ihydroquinone available from Eastman Chemical Products »Inc." under the name of Tenox factory "TBHQ? tocoferolee naturalee available from Eastman Chemical Products »Inc.» under the brand name TenoxR GT-l / GT-2? and hydro? ianisol buti lada from Eastman Chemical Products »Inc.» as BHA »the long chain esters (Cß-Caa: from gallic acid such as dodecyl gallate? Irganox" 1010? Irganox * 1035? Irgano? * B 1171? Irgana? * 1425? Irganox ^ 3114? Irganox * 3125? And mixtures thereof? Preferably Irganox1"* 3125» Irgana? * 1425 »Irganox, H 3114 »and mixtures thereof? and more preferably Ir anoxR 3125 alone or in combination with trio acid and / or other chelating agents such as isopropyl citrate, Dequest® 2010 obtainable from Monsanto under the name of 1-hydroxyethylidene-1-diphosphonic acid (etidronic acid), Pull ** »obtainable from Kodak with a chemical name 4» 5-dihydroxy-benzene sulphonic acid / sodium salt »and OTHER * (diethylenetriaminpentaacetic acid) available from Aldrich. The chemical names are then tabulated with CAS numbers for some of the previous stabilizers.
Antioxidant CAS No. Chemical name used in the code of federal regulations
Irgano? * 1010 6683-19-8 Tetrakis Cmetileno. { 3 »5-di-ter-but i l-4- hydra? I i racinnamate) 3me taño
Irganox.RTM. 1035 41484-35-9 Tiodie ti leno-biß (3 »5-di-tert-butyl 1-4 -hydroxyhydroxycarcinone Irgano * 3098 23128-74-7 N» N '-hexamet i leno-bis (3 » 5-di-ter-buti 1-4- hi drox ih i droc innammami da
Irgano? * E 1171 31570-04-4 Mixture at 1? 1 Irganox * 1098 23128-74-7 and Irgafos * 168
Irganox '65140-91- BisCmonaet i 1 (3 »5-di-tert-butyl l-4-hydroxybeni 1) calcium phosphate Irganox 3114 27676-62-6 1» 3 »5 ~ Tris (3» 5-di- ter-buti l- 4-hydrobenzyl l) -s-triazine- 2 »4» 6- (lH »3H» 5H) trione Irgano? * 3125 34137-09-2 Triéster de ácido 3 »5-di ter ~ butyl l-4-hydroxy-hydrocinic acid with 1 »3» 5 »-tris (2-hydroxyethyl) -S-tricino-2,4,6- (lH» 3H, 5H) -trione Irgafas * 168 31570 -04-4 Tris (2 »4 ~ di-tert-butyl-phenyl> phosphite
Some examples of reducing agents include but are not limited to the same sodium borohydride »sodium bisulfide» hypophosphorous acid and mixtures thereof. The stability of the compounds and compositions herein can be improved by the use of stabilizers, but also the preparation of the compounds used herein and the source of the hydrophobic groups can be important. Surprisingly, some "highly desirable" sources of "highly desirable" sources of hydrophobic groups such as "fatty acids" for example "bait" possess odors that remain with the compound despite the chemical and mechanical process that convert the unprocessed bait into a finished product. Such sources must be deodorized, for example by absorption, distillation, stripping, etc., as is well known in the art. In addition, contact of the resulting fatty acid groups with oxygen and / or bacteria should be minimized by adding antioxidants, antibacterial agents, etc.
ADDITIONAL OPTIONAL INGREDIENTS
Dirt release agent The composition of the present invention may optionally range from 0.1% to 107%, preferably from 0.2% to 5%, of the soil release agent. Preferably the soil release agent is a polymeric soil release agent such as one containing copolymer blocks of terephthalate and polyethylene oxide or polypropylene oxide »cationic guar gums and the like» U.S. Pat. 4 »956» 447 »which is incorporated herein by reference» discloses some preferred soil release agents containing cationic functionalities. A preferred soil release agent is a copolymer having blocks of terephthalate and polyethylene oxide which are composed of repeating units of ethylene terephthalate and polyethylene oxide-terephthalate in a molar ratio of the terephthalate units. from ethylene to the polyethylene oxide-terephthalate units of about 25? 75 to about 35 [deg.] 65"containing said polyethylene oxide-terephthalates, polyethylene oxide blocks having molecular weights of from about 300 to about 2,000. A molecular weight of this palmeric soil release agent is in the range of about 5 ° to about 55,000.
Another preferred polymeric soil release agent is a crystallizable polyester with repeating units of ethylene terephthalate units containing from about 10% to about 15% by weight of units of ethylene terephthalate together with about 107. Approximately 50% by weight of polyoxyethylene glycol having an average molecular weight of about 300 to about 6,000, wherein the mole ratio of the ethylene terephthalate units to the polyoxyethylene terephthalate units in the polymeric compound Ible glass is between 2? 1 and 6? 1. Some examples of this polymer include, but are not limited to, Zelco 1"* 4780 obtainable from DuPont and Mi read" T obtainable from ICI. The highly preferred soil release agents are the polymers of the generic formula (I)?
0 0 0 0 X- (0CHaCH.) (0-C-R * -C-0R2) u < 0-C-R * -C-O) (CHaCHj.0-) n-X
where X can be any suitable spiking group "wherein each X is selected from the group consisting of H" and alkyl or acyl groups containing from about 1 to about 4 carbon atoms "where the preferred methyl is. N is selected for solubility in water and is generally from about 6 to about 113, preferably from about 20 to about 50.
For liquid formulations »u is critical for liquid formulations that have a relatively high ionic strength. The amount of material in which u is greater than 10 should be reduced to the minimum "while there should be at least 207. preferably at least 40% material in which u varies from about 3 to about 5. The portions of R * are essentially 1 * 4-phenyl portions. As used herein, the term "the portions of R 1 are essentially 1, 4-phenylene portions" refers to compounds in which the R 1 portions consist entirely of 1, 4-phenyl or substituted portions. partially with another portion of arylene or alkarylene »alkyl portions» alkynylene moieties or mixtures thereof. The arylene and alkarylene portions that can be partially substituted by 4-phenylene include 1 > 3-phenylene, 1, 2-phenylene, 1.8-naphthalene, 1-naphthalene, 2-biphenylene, 4-phenyl, and mixtures thereof. The alkylene and alkenylene portions which may be partially substituted include ethylene, 1-propylene, 1, 4-bucylene, 1-pentane, 1-hexamethyl, or 7-heptamethyl. »8-actameti wood» 1 »4-cycloexi wood and mixtures thereof. For the portions of R 1, the degree of partial substitution with different portions of the 4-phenylene should be such that the dirt release properties of the compound are not adversely affected to a significant degree. Generally, the degree of partial substitution that can be tolerated will depend on the length of the bae structure of the compound, the longer base structures generally having greater partial substitution for the 1 to 4-phenyl portions. Usually the compounds in which the R1 comprises from about 50% to 1007% of portions of the 4-phenylene (from 0 to about 50% of different portions of 1,4-phenylene) have liberating activity. of adequate dirt. For example, polyesters with a molar ratio of 40 to 60 isophthalic acid (1 to 3-phenol) to terephthalic acid (1, 4-phenol) have suitable soil release activity. However, since most polyesterers in the manufacture of fibers comprise ethylene terephthalate units, it is usually desirable to minimize the degree of partial substitution with different portions of the 4-phenylene for the best release activity. dirt. Preferably, the parts R1 consist entirely (ie, it comprises 100%) in 1 → 4-phenylene portions, ie each portion R1 is 1 »4-phenyle. For the R3 * portions the appropriate ethylene or substituted ethylene moieties "include" but are not limited thereto »ethylene» 1 »2-propylene» 1 »2-butylen» 1 »2-hexylene» 3-methoxy 1 »2-propi len and mixtures thereof. Preferably, the R35 moieties are essentially ethylene moieties, moieties or mixtures of laezee. The inclusion of a higher percentage of ethylene portions tend to improve the dirt release activity of the compounds. The inclusion of a higher percentage of 1, 2-propyl portions or tends to improve the water solubility of the compounds. The use of 1 »2-propylene or a similar branched equivalent is desirable for the incorporation of any substantial part of the soil release component of the liquid textile softening compositions. Preferably from about 75% to about 100%. Most preferably from 90% to about 100%., 2-propi leño. The odor of each n is at least about 6 and is preferably at least about 10. The value for each n usually ranges from about 12 to about 113. Typically, the odor for n is in the range of approximately. 12 to about 43. The cellulose derivatives are also functional as dirt release agents. Some examples of such agents include but are not limited to the same cellulose hydroxytether talee as methocel? obtainable from Sow Chemical; and certain cationic cellulose ether derivatives such as Polymer JU-1251 * »JR-400pt» and JR-30M? obtainable from Union Carbide. Some additional examples of cellulose polymeric soil release agents include methylcellulose, hydroxypropylmethylcellulose, hydrobutyl, ethoxycellulose, or mixtures thereof, wherein said cellulosic polymer contains a viscosity in an aqueous solution at 27. at 20 ° C of 15 to 75,000 centripoices. . Other effective soil release agents are cationic guar gums such as Jaguar Plus obtainable from Stein Hall and Gendrive 458? obtainable from General Mills. A more complete description of highly preferred soil release agents referred to in the European patent application No. 185,427 of Gosselink which was published on June 25, 1986 and the patent of E.U.A. No.5 »207» 933 of Trinh et al. Issued May 4, 1993 »both incorporated herein by reference.
Some examples of Bactericides that can be employed in the compositions of the present invention include but are not limited to the "paraben-like methyl" glutaraldehyde »formaldehyde» 2-bramo-2-nor tropropane-1 »3-diol sold by Inolex Chemicals with the factory name Bronopol "*" and a mixture of 5-chloro-2-met i l-4-isot-aiazol-ina-3-one and 2-met i l-4-eot-aiazol ina-3-one sold by Rohm and Haes Company under the factory name KathonR CG / CP.The typical levels of bactericides used in the present compositions are from about 1 ppm to about 2000 ppm by weight of the composition "depending on the type of bactericide selected. it is especially effective for the development of mold in aqueous fabric softening compositions with less than 107% of the diester component.
S Jcongs Methylene poly (silicone) or modified silicone "can be added to the composition of the present invention" in order to realize the softening property in the water absorbency of the mixture of unsaturated quaternary ammonium salts of the Formula (I) - (III). The dimethylpolysiloxane with β-silicon is preferred by modifying it having a viscosity of 20-10,000 cps at 25 ° C. The modified silicones useful in the present invention include »for example» silicone modified with polyoxyethylene and amino-modified silicone »wherein the amount of the modification is preferably less than 10%. It is preferable that the dimethyl polysiloxane or the modified silicones be emulsified with ionic surfactant of the polyoxyethylene type or a cationic surfactant of the monoalkyl cation type or dialkyl cationic type before use.
Other Optional Components The present invention may include other optional components conventionally used in textile treatment compositions, eg, "conservative dyes," optical brighteners or pacifiers, "fabric conditioning agents," "surfactants," stabilizers such as guar gum. anti-congimienta »ant i-wrinkled agents» fabric tightening agents »ant i-staining agents» fungicides »anticorrosion agents» anti-foam agents and the like. An optional additional softening agent of the present invention is nonionic fabric softening material. Typically, such non-ionic fabric softener materials have a BHL of from about 2 to about 9% more typically from about 3 to about 7. Such non-ionic fabric softening materials tend to disperse easily either on their own or when they are in contact. combination with other materials such as single long chain alkyl cationic surfactants »mix with other materials as set forth below in the preamble» the use of hotter water and / or stirring. In general, the selected materials should be relatively crystalline with higher melting (for example 50 ° C or higher) and relatively insoluble in water. The level of optional nonionic softener in the solid composition is typically from about 10% to about 40% »preferably from about 15% to about 30%» and the ratio of the optional non-ionic softener to the quaternary ester (TEQ) ) of the present invention is from about 1-6 to about 1? 2"preferably from about 1? 4 to about 1? 2" The level of optional nonionic softener in the liquid composition is typically about 0.57. to about 10%, preferably from about 1% to about 5%. Preferred nonionic softeners are partial ethers of fatty acids of polyhydric alcohols, or anhydrides thereof, wherein the alcohol, or the anhydride, contains to about 18"preferably from 2 to about 8, carbon atom" and each fatty acid portion contains from about 12 to about 13"preferably from about 16 to about 20" carbon atoms. Typically, such a softener contains from about 1 to about 3, preferably about 2, fatty acid groups per molecule. The polyhydric alcohol portion of the ester can be ethylene glycol »glycerol» pali (v. Gr., tri- »tetra-, penta-» and / or hexa-) glycerol »xylitol» sucrose »erythritol» pentaerythrol »sorbitol or eorbitan are particularly preferred sorbitan and monostearate esters of pol igl i cerol. The fatty acid moiety of the ester is usually derived from fatty acids having from about 12 to about 13, preferably from about 16 to about 20, carbon atoms, examples of said fatty acids being lauric acid, myristic acid, palmitic acid, and the like. »Stearic acid and behenic acid.
Optional highly nonionic softening agents in the present invention include but are not limited to sorbitan esters, which are esterified esterification products of sorbitol, and glycerol esters. Sarbital, which is typically prepared by the catalytic hydration of glucose, they can be dehydrated in a well known manner to form mixtures of 1-4-yl-5-sorbitol anhydrides and small amounts of isosorbides. An exemplary procedure is described in the US patent. Na 2 »322» 821 which is incorporated herein by reference. The preceding types of complex mixtures of sarbitol anhydrides are collectively referred to herein as "sorbitan". In addition »someone with ordinary skill in the art will recognize that this" sorbitan "mixture will also contain some free sorbitol" not cured. Preferred sorbitan softening agents can be prepared by the "sorbitan" mixture with a fatty acyl group in the usual manner, eg, from the reaction with a fatty acid halide or fatty acid. The esterification reaction can occur in any of the obtainable hydroxyl groups and various mono- »di-» etc. esters can be prepared. The mixtures of mono- »di-» tri- »etc.» esteree are almost always recycled from such reactions and the ratios, stoichiometric of the reactants can be adjusted simply to favor the desired reaction product.
For commercial production of sorbitan ester materials, etherification and esterification are generally carried out in the same process step by reacting eorbitol directly with fatty acids. Is this method described in more detail in MacDonal? "Emulsiffiere." Processing and Quality Control? »Journal of the American 01 i Chemists' Society» Vol. 45 »October 1968. The details» including formulas of the preferred sorbitan esters »can be found in the patent of E.U.A. No 4 »128» 484 »which is incorporated herein by reference. Certain derivatives of the sorbitan esters referred to herein especially "lower" ethoxylates of the same (i.e., mono- "di-" and triesters) wherein one or more of the non-esterified -OH groups contain one or more Approximately 20 portions of oxyethylene p "weens.RTM. are also useful in the composition of the present invention. Therefore," for the purposes of the present invention "the term" sorbitan steres "includes such derivatives. invention »it is preferred» if sorbitan esters are used »that an amount of di- and tri-esters of sorbitan is present in the ester mixture, ester mixtures having 20-50% diester and 10-35% % of tri- and tetraesters are preferred.Commercially obtainable material such as sorbitan monoester (eg, monostearate) "contains significant amounts of di- and tri-esters and a typical analysis of sarbmonostearate. It indicates that it comprises approximately 27% mono- »32% di- and 30% tri- and tetra-esters. Commercial sorbitan monostearate is therefore a preferred material. The mixtures of sorbitan stearate and sorbitan palmitate having weight ratios of stearate / palmitate ranging from 10? 1 and 1? 10 and the esters of 1, 5-sorbit are useful. Both 1,4- and 1,5-sorbitan ethers are also useful herein. Other alkyl sorbitan esters useful for use in the softener compositions herein include sorbitan monolaurate, sorbitan monlimistate, sorbitan monopalmitate, sorbitan onobehenate, sorbitan monooleate, sorbitan dilaurate, sorbitan dimyristate, sorbitan dipalmitate. sorbitan distearate »sorbitan dibehenata, sorbitan dioleate and mixtures thereof» and monobore and di-esters of baboalqui Isorbi tan. Three mixtures were easily prepared by reacting the above hydroxy-substituted sorbitans, particularly the 1, 4- and 1 »5-sorbides» with the corresponding acid or acid chloride in a simple esterification reaction. It should be recognized, of course, that the commercial materials prepared in this way will comprise mixtures usually containing minor proportions of uncyclized sorbitol, fatty acids, polymers, isobromide structures and the like. In the present invention it is meant that such impurities are present at as low a level as possible. The highly preferred sorb esters can contain up to about 15% by weight of fatty acid esters of CaO ~ C = t &; and higher »as well as smaller amounts of lower Ca fatty esters» glycerol and polyglycerol esters are preferred here, especially mono- and / or di-, preferably mono-, glycerone, diglycerol, triglycerol and polyglycerol esters. The glycerol esters can be prepared from glycerides present in nature by standard extraction methods, purification and / or intereeterification or by esterification processes of the type set forth herein above for the eorbitan ethers. Partial glycerin esters can also be ethoxylated to form usable derivatives which are included within the term "glycerol esters". The useful glycerol and polyglycerol esters include monoesters with palpable, oleic, lauric, isaestearic, myristic and / or behenic stearic acid and diesters of bean stearic and alethic acid. The typical monoester contains a little di- and tri-ester »etc. The "glyceral esters" also include the glyceryl esters "for example diglycerol to octagl icerol. The polyglycolral polyols are formed by condensing glycerin or ep chlorohydrin with one another to crosslink the glycerol moieties via ether linkages. The mono- and / or diesters of the polyglycerol polyols are preferred, the fatty acyl groups typically being those described hereinabove for the sorbitan and glycerol esters. The present invention will now be illustrated from the following limiting examples.
E ENP ^ Q l PROCEDURE FOR PREPARING A SOFTENING COMPOSITION WITH
I GRADIENT ACTIVQ A ^ 907,
Material balance - TEEA HTB «1.42 g Hypophosphorous acid (50% solution = 1.24 g Distilled bait or C1 < fa-Clß with acid = 710 g unsaturated fatty acid of Cx Triethanolamine (TEA) 231.8 g
TEA (TEA fatty acid ester amine) is prepared in a pot with 21 resin connected to a stirrer on top »a column of three-spun Snyder» an addition funnel »a distillation equipment» a nitrogen sprayer and a temperature control »The system was tested for vacuum leakage before starting the experiment» Molten fatty acid »anti-oxidant and hypophosphorous acid were introduced into the reaction flask and kept at 65-75 ° C under nitrogen . The reaction apparatus was then purged by extracting the vacuum at 737 mmHg and interrupting the vacuum with nitrogen three times in order to remove all the air in the ßiεtem. TEA was then added and after the addition »the reaction mixture was heated at a ramp rate of 1.75 ° C per minute. According to the reaction temperature reached 105 ° C »the vacuum was removed at 660 mmHg and the reaction continued heating up to 195-200 ° C. At this temperature and pressure the reaction was maintained for approximately 20 minutes. The free fatty acid was approximately p.07 meq / g. The humidity level should be < 0.1% or drying may be required before quaternization.
Material balance - ester quaternary (TEQ) of the present invention TEEA = 306.3 g Isopropanol = 41.3 g DMS = 62.1 g EDTA (40% solution) = 0.26 g BHT = 0.21 g
TEEA was introduced into the reactor and heated to 80 ° C under nitrogen and dried for approximately 30 minutes. It was cooled after the TEEA dried at 60 ° C after which isopropanol (5% by weight batch) was added. The heat jacket was removed and the DMS was added dropwise over a period of approximately 20 minutes. The reaction temperature increased from about 50 ° C to 85 ° C because of the exotherm. The contents of the reactor were allowed to assimilate at 85-90 ° C for about two hours. EDTA and HTB were then added and added to the mixture in remaining isapropanol (5%). The resulting product had the following characteristics?
Appearance? viscous liquid at room temperature
Solvent? isopropanol (IPA) Activity? 90% active ingredient Color (Gardener scale)? 2 pH (17. in IPA? Water at 50/50)? 3-4 Specific gravity? 0.978 g / cm3 Turbidity point? 38-39 ° C Gravity tip? 19-21 ° C Water? 0.5% or less Ester distribution (% by weight); monkey; di i tri is 26.5? 59.5? 10.5 EflIPtQ g "Typical" softener formulation for rinse cycle (7.57 liters of active ingredient)
Starting materials? Quaternary salt of the present invention 8.47. Deionized water 91.60% HCl at 1 N pH 2.7-3.2 Fragrance how much is enough
Dyeing / coloring as long as it is enough
Ant i - my crobiano how much is enough
Heat the water previously between 45 and 60 ° C. Add the heated water to a suitable vessel and acidify to a pH of 2.7-3.2, with HCl to IN. Add the gradually warm quaternary salt in acidified water while stirring and maintain a temperature of 45-60 ° C. Cool the dispersion while you shake it. Solubi lish the fragrance to the softening dispersion at 40 ° C. Add tincture and preservative as desired. * Adjust the weight with Di-water. The dispersion is stable in storage within a temperature range of 4 to 50 ° C.
? vJEM Q 3"Ultra" softener formulation for wash cycle (24% active ingredient)
Materials, starting? Quaternary salt of the present invention 26.80% Deionized water 73.20% 1 N HCl pH 2.7-3.2 10% aqueous solution of calcium chloride chloride < CaCla > Fragrance how much is enough
Dyeing / coloring as long as it is enough
Anti- i Crabian how much is enough
Preheat the deionized water to 50-60 ° C. Introduce the deionized water into the mixing vessel and acidify the water to a pH of 2.7-3.2 with HCl to IN. Add quaternary salt moderately heated to acidified water
0 with agitation while maintaining a temperature of 50-60 ° C. After the addition of 73% of active ingredient »Add the CaCl solution? to IB dispersion in agitation. Make a second salt addition after adding 84% of active ingredient and a third minor salt addition to the
? 5 finish the action of the active substances. Continue the agitation to ensure a homogeneous and uniform dispersion. Enfrieee at 40 ° C with agitation. Solubi l isece the fragrance with the softening dispersion. Adjust the viscosity to the desired level with the addition of the CaCla solution. Add color and conservative. Adjust the weight with deionized water. The dispersion is stable in storage within a temperature range of 4-50 ° C. For an even higher level of smoothing, the dispersions containing 28-40% of active substances can be easily formulated using techniques similar to those shown above.
EXAMPLE 4 rQRMUtAgATiON s AVKjgA T? U A P PA CH Q pe E JUAGUE < 2fly PE ACTIVE SUBSTANCES)
Starting materials? Quaternary salt of the present invention 156 g Deionized water 315 g HCl at IN pH 2.7-3.2 10% aqueous solution of calcium chloride (CaClß) Fragrance as long as it suffices
Dyeing / coloring as long as it is enough
Antimicrobial how much is enough
The deionized water is preheated to 50-60 ° C and introduced into the mixing vessel and acidified to a pH of 2.7-3.2 with HCl to IN. The molten quaternary salt is then slowly added to the mixing vessel while mixing the temperature at about 60 ° C. The mixture is then cooled to 40 ° C with stirring where the fragrance dissolves to softening. The viscosity is then adjusted to the desired level with the addition of the CaCla solution and color and preservatives are added. Finally »ße adjusts the weight with deionized water. The dispersion is stable in storage within a temperature range of 4-50 ° C.
Claims (32)
1. - A fabric softening composition and improved softening performance and stability comprising an antifouling fabric softening amount of a mixture of quaternary ammonium salts having mono- and di-triester components of the following formulas (I) - (III )? 0 (I) R-C-O-R '. R '-OH \ x- N / HO-R'. R ". (II) wherein each R can be the same or different and is represented by a substituted or unsubstituted hydrocarbon radical having 12-22 carbon atoms and an iodine value of 20 to 90 »R? '' R '' and '' are independently selected from the alkyl groups of Ca-C ^, '' is straight or branched chain alkyl of C, -C3 or Ct-C10 aralkyl '' and wherein said di- stes (II) contains more than 557. by weight and the triester component (III) contains less than 257. »based on the total amount of the quaternary ammonium salt mixture.
2. The softening composition according to claim 1, further characterized in that the ratio of isomers to tracer of said mixture of quaternary ammonium salts is in the range of 80/20 to 95/5.
3. The softening composition according to claim 1, characterized in that the cis / trans ratio is greater than 90/10.
4. The softening composition according to claim 1, further characterized in that said mixture of quaternary ammonium salts constitutes 3-50% by weight "based on the total weight of the composition.
5. The softening composition according to claim 1, further characterized in that said mixture of quaternary ammonium salts contains more than 557 by weight of the diester component (II) and less than 20% by weight of the tri-ester component (III).
6. The softening composition according to claim 1, further characterized in that said mixture of quaternary ammonium salts contains more than 60% by weight of the diester component (II) and less than 157. by weight of the triester component (III).
7. The softening composition according to claim 1, further characterized in that said R groups represent a hydrocarbon radical having 16 to 22 carbon atoms and an iodine value of 30 to 60.
8. The softening composition in accordance with the claim 1"further characterized in that said groups R represent a hydrocarbon radical having from 16 to 22 carbon atoms and an iodine value from 45 to 55.
9.- A process for the preparation of a mixture of quaternary monium salts which comprises reacting »at a temperature of 170 ° C to 210 ° C? (I) a substituted or unsubstituted fatty acid of Ctz-CaS ° a mixture of fatty acids having an iodine value of 20 to 90 and having less than about 20% trans double bonds »with (II) an alkanolamine of the formula? R. R. N R. wherein R3 »Rt and z are independently selected from hydroxyalkyl groups of Ca-C ^" wherein the malar ratio of said fatty acid to the alkanolamine is 1.6-1.8"and wherein said reaction temperature is increased by 70 °. C at a range of 170 ° to 210 ° C "wherein the reaction temperature is maintained within a range of 170 ° to 210 ° C until the reaction product has an acid value of less than 5 and wherein the The temperature increase is maintained within a range of approximately 0.8 ° -3 ° C / minute in order to obtain an ester composition with more than 557% by weight of the diester component and less than 25% by weight of the triester component. quaternize the same with the straight-chain or branched-chain-phosphate-carbonate or straight-chain binders of Cj-C, aralkyl-halides, -phosphonates or Ct-C10 sulfates or mixtures thereof order to obtain a mixture of quaternary ammonium saltse.
10.- The procedure according to claim 9 »characterized in that the temperature of the reaction increases at a rate of 1.25 ° -3 ° C / minute from a starting temperature of 70 ° C to a temperature of 170 ° C to 210 ° C.
11. The process according to claim 9, further characterized in that said fatty acid is substituted or unsubstituted C1A-Ca2 fatty acid having an iodine value of 30 to 60.
12. The process according to the claim 9"further characterized in that said fatty acid is a substituted or unsubstituted C14-Caa fatty acid having an iodine value of 45 to 55.
13. The process according to claim 11" further characterized in that said fatty acid is derived from sebum »soybean» palm »palm seed» rapeseed »butter or mixtures thereof.
14. The process according to claim 11, further characterized in that said fatty acid is derived from partially hydrogenated tallow »soybean» palm »palm seed» rape seed, butter or mixtures thereof.
15. The process according to claim 9"further characterized in that said alkanol mine is selected from the group consisting of triethanolamine» propanold ethanolamine »ethanol di isopropanolamine» tisopropanola ina and mixtures thereof.
16.-The procedure in accordance with the reivinid. cation 9 »further characterized in that the molar ratio of the fatty acid to the alkanolamine is 1.7.
17. - The method according to claim 9 »further characterized in that said fatty acid has less than 107. of trans-isomer.
18. The process according to claim 9, further characterized in that the alkylating agent is selected from the group consisting of methyl chloride, benzyl chloride, diethyl sulfate, dimethyl carbonate, trimethyl phosphate, dimethyl sulfate. or mixtures thereof.
19. The method according to claim 9, further characterized in that a solvent is not used during quaternization.
20. The process according to claim 9 »further characterized in that a solvent is used during quaternization.
21. The process according to claim 20, further characterized in that said solvent is selected from the group consisting of alcohols of fatty acid, mono-, di- or triglycerides and mixtures thereof.
22. A mixture of quaternary ammonium salts comprising mono- »di- and tripartite components wherein said mixture of quaternary ammonium compounds comprises more than 55% of the diester and menoe component of 25% of the tri-ether component and in that said mixture of Quaternary ammonium salts is the reaction product of? (A) an ester which is the reaction product of an unsubstituted or unsubstituted C ^ -C ^ fatty acid having an iodine value of 20 to 90 and having less than about 207. of trans-dobels bonds and a diaIcanolami of the formula? Rt N Ra (B) an alkylating agent which is selected from straight or branched chain alkyl halides, -phosphates, carbonates or sulfates of C 2 -C. Aralkyl halides, -phosphates or sulphates, or mixtures thereof. same.
23. Mixture of quaternary ammonium salts according to claim 22 »further characterized said fatty acid is derived from tallow» soy »palm» palm seed, rapeseed »butter and mixtures thereof.
24. A mixture of quaternary ammonium salts according to claim 22, further characterized in that said fatty acid is derived from partially hydrogenated tallow »soybean» palm »palm seed» rapeseed »butter and mixtures thereof.
25. Mixture of quaternary ammonium salts according to claim 22 »further characterized in that said alkanolamine is selected from the group consisting of triethanolamine» propanoldiethanolamine »ethanol di isopropanolamine» tri isopropanole and mixtures thereof.
26.- Quaternary ammonium salt mixture according to claim 22 »further characterized in that the alkylating agent is selected from the group consisting of methyl chloride» benzyl chloride »diethyl sulfate» dimethyl carbonate »trimethyl phosphate» dimethyl sulfate or mixtures thereof.
27. A mixture of quaternary ammonium salts according to claim 22, further characterized in that the molar ratio of the fatty acid to said alkanolamine is 1.7.
28.- Quaternary ammonium salt mixture according to claim 22 »further characterized in that it comprises more than 60% by weight of the diisther component and less than 15% by weight of the triester component.
29. A mixture of quaternary ammonium ealee derived from the reaction of a fatty acid and an alkanolamine comprising mono- »di- and triéether components of the following formulas (I) - (III); 0 R-C-O-R 'R', - OH \ (II) N / R-C-O-R 'R' OR wherein R represents a hydrocarbon radical having 12-22 carbon atoms and an iodine value of between 20 and 90 »Rtr» R2r and R3 'are independently selected from Cß-CC alkyl groups in a straight-chain alkyl or branched of C ^ -C-, or an aralkyla of C-, .- C10 »and where said diester component (II) comprises more than 60% by weight and the triester component (III) comprises less than. 25% by weight »based on the total amount of the mixture of quaternary ammonium salts.
30. A method for softening textile products comprising applying to them an effective softening amount of the composition of claim 1.
31. - A method for smoothing "conditioning and / or lubricating the hair or skin comprising applying to said hair to skin an effective softening and conditioning agent and lubricant of the mixture of quaternary ammonium salts of claim 22. 32.- The process in accordance with Claim 9 »further characterized in that the reaction temperature is maintained within the range of 170 ° C to 210 ° C for about 20 minutes.
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