WO2000006680A1 - Fabric care compositions - Google Patents
Fabric care compositions Download PDFInfo
- Publication number
- WO2000006680A1 WO2000006680A1 PCT/US1998/015955 US9815955W WO0006680A1 WO 2000006680 A1 WO2000006680 A1 WO 2000006680A1 US 9815955 W US9815955 W US 9815955W WO 0006680 A1 WO0006680 A1 WO 0006680A1
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- WO
- WIPO (PCT)
- Prior art keywords
- mixtures
- units
- alkyl
- formula
- group
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 206
- 239000004744 fabric Substances 0.000 title claims abstract description 54
- -1 nitrogen containing compound Chemical class 0.000 claims abstract description 96
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 62
- 229920001002 functional polymer Polymers 0.000 claims abstract description 38
- 239000004094 surface-active agent Substances 0.000 claims abstract description 32
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 28
- 125000002091 cationic group Chemical group 0.000 claims abstract description 22
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 15
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 14
- 238000005406 washing Methods 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 56
- 229920000768 polyamine Polymers 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 239000000975 dye Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 16
- 239000005977 Ethylene Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 150000001450 anions Chemical class 0.000 claims description 12
- 239000001913 cellulose Substances 0.000 claims description 12
- 229920002678 cellulose Polymers 0.000 claims description 12
- 239000000985 reactive dye Substances 0.000 claims description 11
- 229960001231 choline Drugs 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 9
- 230000001603 reducing effect Effects 0.000 claims description 7
- 239000003093 cationic surfactant Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- CUXKZYSCZCNPNX-UHFFFAOYSA-N tetradecan-1-amine;hydrobromide Chemical compound [Br-].CCCCCCCCCCCCCC[NH3+] CUXKZYSCZCNPNX-UHFFFAOYSA-N 0.000 claims description 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 230000002829 reductive effect Effects 0.000 abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 80
- 229920002873 Polyethylenimine Polymers 0.000 description 70
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 34
- 239000000126 substance Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 25
- 239000002904 solvent Substances 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 19
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 19
- 239000003760 tallow Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 239000002304 perfume Substances 0.000 description 18
- 239000000463 material Substances 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
- 239000002979 fabric softener Substances 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 239000000194 fatty acid Substances 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 12
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000003599 detergent Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- 102000004190 Enzymes Human genes 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- 229940088598 enzyme Drugs 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 150000001204 N-oxides Chemical class 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 8
- 150000002190 fatty acyls Chemical group 0.000 description 8
- 150000002431 hydrogen Chemical group 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 8
- 108010059892 Cellulase Proteins 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- 239000000828 canola oil Substances 0.000 description 7
- 235000019519 canola oil Nutrition 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 239000003205 fragrance Substances 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 7
- 230000004048 modification Effects 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 238000005956 quaternization reaction Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 150000003335 secondary amines Chemical class 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 6
- 229930002839 ionone Natural products 0.000 description 6
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 6
- 235000019645 odor Nutrition 0.000 description 6
- 125000000962 organic group Chemical group 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 150000003512 tertiary amines Chemical group 0.000 description 6
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 5
- 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 5
- 108010084185 Cellulases Proteins 0.000 description 5
- 102000005575 Cellulases Human genes 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 5
- 229940106157 cellulase Drugs 0.000 description 5
- 239000003240 coconut oil Substances 0.000 description 5
- 235000019864 coconut oil Nutrition 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
- 235000019256 formaldehyde Nutrition 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- 238000003760 magnetic stirring Methods 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 4
- 241000402754 Erythranthe moschata Species 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 4
- 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 4
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 4
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 4
- 238000007046 ethoxylation reaction Methods 0.000 description 4
- 239000000834 fixative Substances 0.000 description 4
- 239000003966 growth inhibitor Substances 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 238000012544 monitoring process Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910021653 sulphate ion Inorganic materials 0.000 description 4
- 229910052720 vanadium Inorganic materials 0.000 description 4
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 3
- QUMXDOLUJCHOAY-UHFFFAOYSA-N 1-Phenylethyl acetate Chemical compound CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 description 3
- ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000019774 Rice Bran oil Nutrition 0.000 description 3
- 235000019485 Safflower oil Nutrition 0.000 description 3
- 239000004902 Softening Agent Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 235000019486 Sunflower oil Nutrition 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
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- JEIKGHMHTDMQIL-UHFFFAOYSA-N ethenol;urea Chemical class OC=C.NC(N)=O JEIKGHMHTDMQIL-UHFFFAOYSA-N 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000002499 ionone derivatives Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229940102398 methyl anthranilate Drugs 0.000 description 3
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 3
- 229940055076 parasympathomimetics choline ester Drugs 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 3
- 150000003248 quinolines Chemical class 0.000 description 3
- 239000008165 rice bran oil Substances 0.000 description 3
- 235000005713 safflower oil Nutrition 0.000 description 3
- 239000003813 safflower oil Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000002600 sunflower oil Substances 0.000 description 3
- 239000003784 tall oil Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 229910052727 yttrium Inorganic materials 0.000 description 3
- VKZRWSNIWNFCIQ-WDSKDSINSA-N (2s)-2-[2-[[(1s)-1,2-dicarboxyethyl]amino]ethylamino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NCCN[C@H](C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-WDSKDSINSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- WRFXXJKURVTLSY-UHFFFAOYSA-N 2,6-dimethyloctan-2-ol Chemical compound CCC(C)CCCC(C)(C)O WRFXXJKURVTLSY-UHFFFAOYSA-N 0.000 description 2
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical class CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VHDFCBMXCOUFOE-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid Chemical compound OCC(N)(CO)CO.CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 VHDFCBMXCOUFOE-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- PMUNIMVZCACZBB-UHFFFAOYSA-N 2-hydroxyethylazanium;chloride Chemical compound Cl.NCCO PMUNIMVZCACZBB-UHFFFAOYSA-N 0.000 description 2
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 2
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 description 2
- PRNCMAKCNVRZFX-UHFFFAOYSA-N 3,7-dimethyloctan-1-ol Chemical compound CC(C)CCCC(C)CCO PRNCMAKCNVRZFX-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
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- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- FUQAYSQLAOJBBC-PAPYEOQZSA-N β-caryophyllene alcohol Chemical compound C1C[C@](C2)(C)CCC[C@]2(O)[C@H]2CC(C)(C)[C@@H]21 FUQAYSQLAOJBBC-PAPYEOQZSA-N 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
- C11D1/42—Amino alcohols or amino ethers
- C11D1/44—Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3723—Polyamines or polyalkyleneimines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/12—Soft surfaces, e.g. textile
Definitions
- the present invention relates to a fabric care compositions and more particularly to a method and a composition which exhibit reduced or even no formation of scum on the fabrics and/or the washing machine parts whilst still providing care to the colors of fabrics treated therewith.
- Dye fixing components as described in EP462806 are suitable components for this purpose. Indeed, these components provide care to the color of fabrics by assisting in binding the loosely held dye to the fabric.
- compositions comprising such dye fixing agent and/or amino-functional polymer are characterized by the resulting scum which forms on the treated fabrics and/or the washing machine parts.
- the formulator of a fabric care composition is faced with the dual challenge of formulating a composition which exhibit reduced or even no formation of scum but without being detrimental to the colors of the treated fabrics.
- a scum reducing agent selected from a water-soluble cationic surface active agent; a polyoxyalkylene alkyl amine surface active agent, and mixtures thereof, to compositions comprising a nitrogen containing compound selected from an amino-functional polymer, a dye fixing agent and mixtures thereof, overcomes the problem.
- the present invention relates to a fabric care composition
- a fabric care composition comprising i)- a nitrogen containing compound selected from a polyamino-functional polymer, a dye fixing agent, and mixtures thereof, and ii)- a scum reducing agent selected from a water-soluble cationic surface active agent; a polyoxyalkylene alkyl amine surface active agent, and mixtures thereof; with the proviso that when the sole nitrogen containing compound is a polyamino-functional polymer, the polymer is present in amounts greater than 1% by weight.
- a composition comprising a nitrogen containing compound selected from a polyamino-functional polymer, a dye fixing agent, and mixtures thereof, for reducing or preventing the formation of scum on fabrics or washing machine parts contacted with the composition.
- a fabric care composition with effective and durable color care properties.
- An essential component of the invention is a nitrogen containing compound selected from an amino-functional polymer, a dye fixing agent, and mixtures thereof.
- the amino-functional polymer advantageously provides care to the colors of fabrics.
- the amino-functional polymers of the present invention are water-soluble or dispersible, polyamines.
- the amino-functional polymers for use herein have a molecular weight between 200 and 10 ⁇ , preferably between 600 and 20,000, most preferably between 1000 and 10,000.
- These polyamines comprise backbones that can be either linear or cyclic.
- the polyamine backbones can also comprise polyamine branching chains to a greater or lesser degree.
- the polyamine backbones described herein are modified in such a manner that at least one, preferably each nitrogen of the polyamine chain is thereafter described in terms of a unit that is substituted, quaternized, oxidized, or combinations thereof.
- the term "modification" as it relates to the chemical structure of the polyamines is defined as replacing a backbone -NH hydrogen atom by an R' unit (substitution), quaternizing a backbone nitrogen (quaternized) or oxidizing a backbone nitrogen to the N-oxide (oxidized).
- substitution and “substitution” are used interchangably when referring to the process of replacing a hydrogen atom attached to a backbone nitrogen with an R' unit. Quaternization or oxidation may take place in some circumstances without substitution, but substitution is preferably accompanied by oxidation or quaternization of at least one backbone nitrogen.
- the linear or non-cyclic polyamine backbones that comprise the amino-functional polymer have the general formula: I
- primary amine nitrogens comprising the backbone or branching chain once modified are defined as V or Z "terminal" units.
- V or Z "terminal" units when a primary amine moiety, located at the end of the main polyamine backbone or branching chain having the structure
- H2N-[R]- is modified according to the present invention, it is thereafter defined as a V "terminal" unit, or simply a V unit.
- V terminal
- some or all of the primary amine moieties can remain unmodified subject to the restrictions further described herein below. These unmodified primary amine moieties by virtue of their position in the backbone chain remain “terminal” units.
- Z Z "terminal" unit, or simply a Z unit. This unit can remain unmodified subject to the restrictions further described herein below.
- secondary amine nitrogens comprising the backbone or branching chain once modified are defined as W "backbone" units.
- W backbone
- H — [N-R]- is modified according to the present invention, it is thereafter defined as a W "backbone” unit, or simply a W unit.
- W backbone
- some or all of the secondary amine moieties can remain unmodified. These unmodified secondary amine moieties by virtue of their position in the backbone chain remain "backbone” units.
- tertiary amine nitrogens comprising the backbone or branching chain once modified are further referred to as Y "branching" units.
- Y branch point of either the polyamine backbone or other branching chains or rings, having the structure
- V(n+1)W m Y n Z for linear amino-functional polymer and by the general formula V ⁇ -k+ WmYnY'kZ for cyclic amino-functional polymer.
- [N-R]— serves as a branch point for a backbone or branch ring.
- Y' unit there is a Y unit having the formula
- the polyamine backbone has the formula
- the polyamine backbones of the present invention comprise no rings.
- the ratio of the index n to the index m relates to the relative degree of branching.
- a fully non-branched linear modified polyamine according to the present invention has the formula VW m Z that is, n is equal to 0. The greater the value of n (the lower the ratio of m to n), the greater the degree of branching in the molecule.
- the value for m ranges from a minimum value of 2 to 700, preferably 4 to 400, however larger values of m, especially when the value of the index n is very low or nearly 0, are also preferred.
- Each polyamine nitrogen whether primary, secondary or tertiary, once modified according to the present invention, is further defined as being a member of one of three general classes; simple substituted, quaternized or oxidized. Those polyamine nitrogen units not modified are classed into V, W, Y, Y' or Z units depending on whether they are primary, secondary or tertiary nitrogens. That is unmodified primary amine nitrogens are V or Z units, unmodified secondary amine nitrogens are W units or Y' units and unmodified tertiary amine nitrogens are Y units for the purposes of the present invention.
- Modified primary amine moieties are defined as V "terminal" units having one of three forms: a) simple substituted units having the structure:
- Modified secondary amine moieties are defined as W "backbone" units having one of three forms: a) simple substituted units having the structure:
- modified secondary amine moieties are defined as Y' units having one of three forms: a) simple substituted units having the structure: -N-R—
- R b quaternized units having the structure:
- Modified tertiary amine moieties are defined as Y "branching" units having one of three forms: a) unmodified units having the structure: — N-R—
- Certain modified primary amine moieties are defined as Z "terminal" units having one of three forms: a) simple substituted units having the structure: —N-R R b) quaternized units having the structure: R ' x -
- a primary amine unit comprising one R' unit in the form of a hydroxyethyl moiety is a V terminal unit having the formula (HOCH2CH 2 )HN-.
- the Z "terminal” unit derives from a terminal primary amino moiety of the structure -NH2- Non-cyclic polyamine backbones according to the present invention comprise only one Z unit whereas cyclic polyamines can comprise no Z units.
- the Z "terminal” unit can be substituted with any of the R' units described further herein below, except when the Z unit is modified to form an N-oxide. In the case where the Z unit nitrogen is oxidized to an N-oxide, the nitrogen must be modified and therefore R' cannot be a hydrogen.
- the polyamines of the present invention comprise backbone R "linking" units that serve to connect the nitrogen atoms of the backbone.
- R units comprise units that for the purposes of the present invention are referred to as “hydrocarbyl R” units and “oxy R” units.
- the "hydrocarbyl” R units are C2-C-12 alkylene, C4-C12 alkenylene, C3-C12 hydroxyalkylene wherein the hydroxyl moiety may take any position on the R unit chain except the carbon atoms directly connected to the polyamine backbone nitrogens; C4-C12 dihydroxyalkylene wherein the hydroxyl moieties may occupy any two of the carbon atoms of the R unit chain except those carbon atoms directly connected to the polyamine backbone nitrogens; Cg-
- C12 dialkylarylene which for the purpose of the present invention are arylene moieties having two alkyl substituent groups as part of the linking chain.
- a dialkylarylene unit has the formula although the unit need not be 1 ,4-substituted, but can also be 1 ,2 or 1 ,3 substituted C2-C12 alkylene, preferably ethylene, 1 ,2-propylene, and mixtures thereof, more preferably ethylene.
- the "oxy" R units comprise - (RlO) x R 5 (ORl) x -, -CH 2 CH(OR 2 )CH2 ⁇ ) z (R 0) y Rl(OCH 2 CH(OR2)CH2) w -, - CH2CH(OR )CH2-, -(R 1 0) x R 1 -, and mixtures thereof.
- R units are selected from the group consisting of C2-C12 alkylene, C3-C12 hydroxyalkylene, C4-C12 dihydroxyalkylene, C8-C12 dialkylarylene, -(Rl ⁇ ) x Rl-, CH 2 CH(OR 2 )CH 2 -, -(CH 2 CH(OH)CH2O) z (R 0) y R (OCH 2 CH-(OH)CH2) w -, - (R 1 0) x R 5 (OR 1 ) x -, more preferred R units are C-2-C12 alkylene, C3-C12 hydroxy-alkylene, C4-C12 dihydroxyalkylene, -(R 1 0) x R 1 -, -(R 1 0) x R 5 (OR 1 ) x -, -
- R units are C2-C12 alkylene, C3 hydroxyalkylene, and mixtures thereof, most preferred are C2-C6 alkylene.
- the most preferred backbones of the present invention comprise at least 50% R units that are ethylene.
- R1 units are C2-C6 alkylene, and mixtures thereof, preferably ethylene.
- R2 is hydrogen, and -(Rl ⁇ ) x B, preferably hydrogen.
- R 3 is C1-C-18 alkyl.
- C7-C12 arylalkylene, C7-C12 alkyl substituted aryl, C ⁇ -C ⁇ aryl, and mixtures thereof preferably C-1-C12 alkyl, C7-C12 arylalkylene, more preferably C1-C12 alkyl, most preferably methyl.
- R 3 units serve as part of R' units described herein below.
- R 4 is C1-C-12 alkylene, C4-C12 alkenylene, C8-C12 arylalkylene, C6-C10 arylene, preferably C-
- R 5 is C1-C-12 alkylene, C3-C12 hydroxyalkylene, C4-C12 dihydroxyalkylene, C ⁇ - C12 dialkylarylene, -C(O)-, -C(0)NHR 6 NHC(0)-, -C(0)(R4) r C(0)-, -R (OR 1 )-, - CH 2 CH(OH)CH 2 0(Rl ⁇ )yR 1 OCH2CH(OH)CH2-, -C(0)(R 4 ) r C(0)-,
- R 5 is preferably ethylene, -C(O)-, -C(0)NHR6NHC(0)-, - R (OR 1 )-, -CH 2 CH(OH)CH 2 -, -CH 2 CH(OH)CH2 ⁇ (R 1 0) y R 1 OCH 2 CH-(OH)CH2-
- R 6 is C2-C12 alkylene or Cg-C ⁇ arylene.
- the preferred "oxy" R units are further defined in terms of the R1 , R2, and R 5 units.
- Preferred "oxy" R units comprise the preferred R1 , R 2 , and R ⁇ units.
- the preferred cotton soil release agents of the present invention comprise at least 50% R1 units that are ethylene.
- Preferred R 1 , R2, and R ⁇ units are combined with the "oxy" R units to yield the preferred "oxy” R units in the following manner.
- R' units are selected from the group consisting of hydrogen, C1-C22 alkyl, C3- C22 alkenyl, C7-C22 arylalkyl, C2-C22 hydroxyalkyl, -(CH2) p C02M, - (CH 2 ) q S03M, -CH(CH 2 C ⁇ 2M)C ⁇ 2M, -(CH 2 ) p P ⁇ 3M, -(Rl ⁇ ) m B, -C(0)R 3 , preferably hydrogen, C2-C22 hydroxyalkylene, benzyl, C1-C22 alkylene, - (R 1 0) m B, -C(0)R 3 , -(CH 2 ) p C02M, -(CH 2 ) q S0 3 M, -CH(CH 2 C0 2 M)C0 2 M, more preferably C-I-C22 alkylene, -(R 1 0) x B
- R' units do not comprise hydrogen atom when the V, W or Z units are oxidized, that is the nitrogens are N-oxides.
- the backbone chain or branching chains do not comprise units of the following structure:
- R' units do not comprise carbonyl moieties directly bonded to a nitrogen atom when the V, W or Z units are oxidized, that is, the nitrogens are N- oxides.
- the R' unit -C(0)R 3 moiety is not bonded to an N-oxide modified nitrogen, that is, there are no N-oxide amides having the structure
- B is hydrogen, C ⁇
- M is hydrogen or a water soluble cation in sufficient amount to satisfy charge balance.
- a sodium cation equally satisfies -(CH2)pC02M, and
- -(CH2) q S ⁇ 3M thereby resulting in -(CH2) p C02Na, and -(CH2) q S ⁇ 3Na moieties.
- More than one monovalent cation, (sodium, potassium, etc.) can be combined to satisfy the required chemical charge balance.
- more than one anionic group may be charge balanced by a divalent cation, or more than one mono-valent cation may be necessary to satisfy the charge requirements of a poly-anionic radical.
- a -(CH2)pP03M moiety substituted with sodium atoms has the formula -(CH2)pP ⁇ 3Na3.
- Divalent cations such as calcium (Ca2 + ) or magnesium (Mg2 + ) may be substituted for or combined with other suitable mono-valent water soluble cations.
- Preferred cations are sodium and potassium, more preferred is sodium.
- X is a water soluble anion such as chlorine (CI-), bromine (Br) and iodine
- (I-) or X can be any negatively charged radical such as sulfate (SO42-) and methosulfate (CH3SO3-).
- indices have the following values: p has the value from 1 to 6, q has the value from 0 to 6; r has the value 0 or 1 ; w has the value 0 or 1 , x has the value from 1 to 100; y has the value from 0 to 100; z has the value 0 or 1 ; m has the value from 2 to 700, preferably from 4 to 400, n has the value from 0 to 350, preferably from 0 to 200; m + n has the value of at least 5.
- x has a value lying in the range of from 1 to 20, preferably from 1 to
- the preferred amino-functional polymers of the present invention comprise polyamine backbones wherein less than 50% of the R groups comprise "oxy" R units, preferably less than 20% , more preferably less than 5%, most preferably the R units comprise no "oxy" R units.
- the most preferred amino-functional polymers which comprise no "oxy" R units comprise polyamine backbones wherein less than 50% of the R groups comprise more than 3 carbon atoms.
- ethylene, 1 ,2-propylene, and 1 ,3- propylene comprise 3 or less carbon atoms and are the preferred "hydrocarbyl" R units. That is when backbone R units are C2-C12 alkylene, preferred is C2-C3 alkylene, most preferred is ethylene.
- the amino-functional polymers of the present invention comprise modified homogeneous and non-homogeneous polyamine backbones, wherein 100% or less of the -NH units are modified.
- the term "homogeneous polyamine backbone” is defined as a polyamine backbone having R units that are the same (i.e., all ethylene). However, this sameness definition does not exclude polyamines that comprise other extraneous units comprising the polymer backbone which are present due to an artifact of the chosen method of chemical synthesis.
- ethanolamine may be used as an "initiator" in the synthesis of polyethyleneimines, therefore a sample of polyethyleneimine that comprises one hydroxyethyl moiety resulting from the polymerization "initiator” would be considered to comprise a homogeneous polyamine backbone for the purposes of the present invention.
- a polyamine backbone comprising all ethylene R units wherein no branching Y units are present is a homogeneous backbone.
- a polyamine backbone comprising all ethylene R units is a homogeneous backbone regardless of the degree of branching or the number of cyclic branches present.
- non-homogeneous polymer backbone refers to polyamine backbones that are a composite of various R unit lengths and R unit types.
- a non-homogeneous backbone comprises R units that are a mixture of ethylene and 1 ,2-propylene units.
- a mixture of "hydrocarbyl” and “oxy” R units is not necessary to provide a non-homogeneous backbone.
- Preferred amino-functional polymers of the present invention comprise homogeneous polyamine backbones that are totally or partially substituted by polyethyleneoxy moieties, totally or partially quaternized amines, nitrogens totally or partially oxidized to N-oxides, and mixtures thereof.
- polyethyleneoxy moieties totally or partially quaternized amines
- nitrogens totally or partially oxidized to N-oxides, and mixtures thereof.
- backbone amine nitrogens must be modified in the same manner, the choice of modification being left to the specific needs of the formulator.
- the degree of ethoxylation is also determined by the specific requirements of the formulator.
- the preferred polyamines that comprise the backbone of the compounds of the present invention are generally polyalkyleneimines (PAI's), preferably polyethyleneimines (PEI's), or PEI's connected by moieties having longer R units than the parent PAI's or PEI's.
- PAI's polyalkyleneimines
- PEI's polyethyleneimines
- PEI's polyethyleneimines
- Preferred amine polymer backbones comprise R units that are C2 alkylene
- PEI's polyethylenimines
- Preferred PEI's have at least moderate branching, that is the ratio of m to n is less than 4:1 , however PEI's having a ratio of m to n of 2:1 are most preferred.
- Preferred backbones, prior to modification have the general formula:
- PEI's will have a molecular weight greater than 200 daltons.
- the relative proportions of primary, secondary and tertiary amine units in the polyamine backbone will vary, depending on the manner of preparation.
- Each hydrogen atom attached to each nitrogen atom of the polyamine backbone chain represents a potential site for subsequent substitution, quaternization or oxidation.
- These polyamines can be prepared, for example, by polymerizing ethyleneimine in the presence of a catalyst such as carbon dioxide, sodium bisulfite, sulfuric acid, hydrogen peroxide, hydrochloric acid, acetic acid, etc.
- a catalyst such as carbon dioxide, sodium bisulfite, sulfuric acid, hydrogen peroxide, hydrochloric acid, acetic acid, etc.
- amino-functional polymers comprising PEI's
- Formula I depicts an amino-functional polymer comprising a PEI backbone wherein all substitutable nitrogens are modified by replacement of hydrogen with a polyoxyalkyleneoxy unit, -(CH2CH2 ⁇ )H, having the formula
- Formula II depicts an amino-functional polymer comprising a PEI backbone wherein all substitutable primary amine nitrogens are modified by replacement of hydrogen with a polyoxyalkyleneoxy unit, -(CH2CH2 ⁇ )2H, the molecule is then modified by subsequent oxidation of all oxidizable primary and secondary nitrogens to N-oxides, said polymer having the formula
- Formula III depicts an amino-functional polymer comprising a PEI backbone wherein all backbone hydrogen atoms are substituted and some backbone amine units are quaternized.
- the substituents are polyoxyalkyleneoxy units, - (CH2CH2 ⁇ )7H, or methyl groups.
- the modified PEI has the formula
- Formula IV depicts an amino-functional polymer comprising a PEI backbone wherein the backbone nitrogens are modified by substitution (i.e. by - (CH2CH2 ⁇ )3H or methyl), quaternized, oxidized to N-oxides or combinations thereof.
- the resulting polymer has the formula
- not all nitrogens of a unit class comprise the same modification.
- the present invention allows the formulator to have a portion of the secondary amine nitrogens ethoxylated while having other secondary amine nitrogens oxidized to N-oxides.
- This also applies to the primary amine nitrogens, in that the formulator may choose to modify all or a portion of the primary amine nitrogens with one or more substituents prior to oxidation or quaternization. Any possible combination of R' groups can be substituted on the primary and secondary amine nitrogens, except for the restrictions described herein above.
- amino-functional polymers suitable for use herein are poly(ethyleneimine) with a MW 1200, hydroxyethylated poly(ethyleneimine) from Polysciences, with a MW 2000, and 80% hydroxyethylated poly(ethyleneimine) from Aldrich.
- a typical amount of amino-functional polymer to be employed in the composition of the invention when used as sole nitrogen containing compound is of greater than 1%, preferably up to 50% by weight, more preferably from greater than 1% to 25% by weight, and most preferably from greater than 1% to 10% active by weight of the composition.
- Dye fixing agent are well-known, commercially available materials which are designed to improve the appearance of dyed fabrics by minimizing the loss of dye from fabrics due to washing. Not included within this definition are components which are fabric softeners or those described hereinafter as amino- functional polymers.
- Cationic fixatives are available under various trade names from several suppliers. Representative examples include: Cartafix CB from Clariant, CROSCOLOR PMF (July 1981 , Code No. 7894) and CROSCOLOR NOFF (January 1988, Code No. 8544) from Crosfield; INDOSOL E-50 (February 27, 1984, Ref. No.
- Dye fixing agents suitable for use in the present invention are ammonium compounds such as fatty acid - diamine condensates e.g.
- Preferred dye fixing agents are the cellulose reactive dye fixing agents.
- cellulose reactive dye fixing agent it is meant that the agent reacts with the cellulose fibers upon heat treatment.
- agents suitable for use herein can be defined by the following test procedure, so called cellulose reactivity test measurement.
- Two pieces of bleeding fabrics e.g. 10 x 10 cm of knitted cotton dyed with Direct Red 80
- an aqueous solution of 1% (w/w) of the cellulose reactive dye fixing agent candidate The pH of the solution is as it is obtained at this concentration.
- the swatches are then dried.
- One of the dried swatches as well as an unsoaked swatch (control 1) are passed 10 times trough an ironing calender set on a linen setting.
- a control 2 swatch is also used in this measurement test which is a non-soaked and non-ironed swatch.
- the 4 swatches are washed separately in Launder-o-meter pots under typical conditions with a commercial detergent used at the recommended dosage for ! hour at 60°C, followed by a thorough rinsing of 4 times 200 ml of cold water and then line dried.
- Delta E is the computed color difference as defined in ASTM D2244, i.e the magnitude and direction of the difference between two psychophysical color stimuli defined by tristimulus values, or by chromaticity coordinates and luminance factor, as computed by means of a specified set of color-difference equations defined in the CIE 1976 CIELAB opponent-color space, the Hunter opponent-color space, the Friele-Mac Adam-Chickering color space or any equivalent color space.
- the candidate is a cellulose reactive dye fixing agent for the purpose of the invention.
- Typical cellulose reactive dye fixing agents are products containing the reactive group of the reactive dye classes selected from halogeno-triazine products, vinyl sulphones compounds, epichlorhydrine derivatives, hydroxyethylene urea derivatives, formaldehyde condensation products, polycarboxylates, glyoxal and glutaraldehyde derivatives and mixtures thereof.
- Preferred hydroxyethylene urea derivatives include dimethyloldihydroxyethylene, urea, and dimethyl urea glyoxal.
- Preferred formaldehyde condensation products include the condensation products derived from formaldehyde and a group selected from an amino-group, an imino-group, a phenol group, an urea group, a cyanamide group and an aromatic group.
- Commercially available compounds among this class are Sandofix WE 56 from Clariant, Zetex E from Zeneca and Levogen BF from Bayer.
- Preferred polycarboxylates derivatives include butane tetracarboxilic acid derivatives, citric acid derivatives, polyacrylates and derivatives thereof.
- a most preferred cellulosic reactive dye fixing agents is one of the hydroxyethylene urea derivatives class commercialised under the tradename of Indosol CR from Clariant. Still other most preferred cellulosic reactive dye fixing agents are commercialised under the tradename Rewin DWR and Rewin WBS from CHT R. Beitlich.
- the preferred agent for use in the present invention are cationic, in particular polycationic dye fixing agents.
- a typical amount of the dye fixing agent to be employed in the composition of the invention is preferably from 1% to 50% by weight, more preferably from 1% to 25% by weight, most preferably from 1.5% to 10% active by weight of the composition.
- the total level of these components is typically up to 90% by weight, preferably up to 50% by weight, more preferably from 1 % to 25%. by weight, most preferably from 1% to 10% active by weight of the composition.
- Water-soluble cationic surface active agent By “water-soluble wetting agent”, it is meant that the wetting agent forms substantially clear, isotropic solutions when dissolved in water at 0.2 weight percent at 25°C.
- any type of water-soluble cationic surface active agent can be used to impart the scum reducing property.
- some water-soluble cationic surface active agents and mixtures thereof are more preferred.
- the cationic surfactant is a surface-active molecule with a linear or branched hydrophobic tail and a positively charged hydrophilic head group, more preferably, the cationic surfactant for use in the present invention is quaternary ammonium salt of formula:
- R 1 group is C 10 -C 22 hydrocarbon group, preferably C 12 -C 18 alkyl group or the corresponding ester linkage interrupted group with a short alkylene (C C 4 ) group between the ester linkage and the N, and having a similar hydrocarbon group, e.g., a fatty acid ester of choline, preferably C 12 -C 14 (coco) choline ester and/or C 16 -C 18 tallow choline ester.
- the hydrocarbon group may be interrupted by further groups like COO, OCO, O, CO, OCOO, CONH, NHCO, OCONH and NHCOO.
- Each R is a C r C 4 alkyl or substituted (e.g., hydroxy) alkyl, or hydrogen, preferably methyl, and the counterion X " is a softener compatible anion, for example, chloride, bromide, methyl surface, etc.
- the long chain group R1 of the single-long-chain-alkyl surfactant, typically contains an alkylene group having from 10 to 22 carbon atoms, preferably from 12 to about 16 carbon atoms, more preferably from 12 to 18 carbon atoms.
- This R1 group can be attached to the cationic nitrogen atom through a group containing one, or more, ester, amide, ether, amine, etc., preferably ester, linking groups which can be desirable for increased hydrophilicity, biodegradability, etc. Such linking groups are preferably within about three carbon atoms of the nitrogen atom.
- a preferred cationic surfactant of this type is N,N dimethyl-N-(2- hydroxyethyl)-N-dodecyl/tetradecyl ammonium bromide.
- any acid preferably a mineral or polycarboxylic acid which is added to keep the ester groups stable will also keep the amine protonated in the compositions.
- Typical disclosure of these cationic surfactants suitable for use in the present invention are the choline ester surfactants of formula:
- R-] is a C10-C22 linear or branched alkyl, alkenyl or alkaryl chain or M".
- X and Y independently, are selected from the group consisting of COO, OCO, O, CO, OCOO, CONH, NHCO, OCONH and NHCOO wherein at least one of X or Y is a COO, OCO, OCOO, OCONH or NHCOO group;
- R2, R3, R4, RQ, RJ, and Rs are independently selected from the group consisting of alkyl, alkenyl, hydroxyalkyl and hydroxy-alkenyl groups having from 1 to 4 carbon atoms and alkaryl groups; and
- R5 is independently H or a C1-C3 alkyl group; wherein the values of m, n, s and t independently lie in the range of from 0 to 8, the value of b lies in the range from 0 to 20, and the values of
- M is selected from the group consisting of halide, methyl sulfate, sulfate, and nitrate, more preferably methyl sulfate, chloride, bromide or iodide.
- Highly preferred water soluble choline ester surfactants are the esters having the formula: O CH 3
- n is from 1 to 4, preferably 2 or 3 and wherein Ri is a C ⁇
- 1 alkyl), cocoyl choline ester quaternary methylammonium halides (R1 CH _C-I 3 alkyl), tallowyl choline ester quaternary methylammonium halides alkyl), and any mixtures thereof.
- choline esters of this type are selected from myristoyl choline ester quaternary methylammonium halides, lauroyl choline ester methylammonium halides, cocoyl choline ester quaternary methylammonium halides, and any mixtures thereof.
- the particularly preferred choline esters may be prepared by the direct esterification of a fatty acid of the desired chain length with dimethylaminoethanol, in the presence of an acid catalyst.
- the reaction product is then quaternized with a methyl halide, preferably in the presence of a solvent such as ethanol, water, propylene glycol or preferably a fatty alcohol ethoxylate such as C10-C18 fatty alcohol ethoxylate having a degree of ethoxylation of from 3 to 50 ethoxy groups per mole forming the desired cationic material.
- a solvent such as ethanol, water, propylene glycol or preferably a fatty alcohol ethoxylate such as C10-C18 fatty alcohol ethoxylate having a degree of ethoxylation of from 3 to 50 ethoxy groups per mole forming the desired cationic material.
- They may also be prepared by the direct esterification of a long chain fatty acid of the desired chain length together with 2-haloethanol
- Polyoxyalkylene alkyl amine surface active agent A polyoxyalkylene alkyl amine surface active agent is also another essential component of the present invention composition. Indeed, by means of this component, the formation of scum is reduced or even prevented.
- polyoxyalkylene alkyl amine nonionic surfactants suitable for use in the present invention have the formula:
- R 4 ( R 4 ) verse wherein R is selected from C7-C21 linear alkyl, C7-C21 branched alkyl, C7-C21 linear alkenyl, C7-C21 branched alkenyl, and mixtures thereof.
- the nonionic surfactants of the present invention are derived from synthetic or naturally occurring feedstocks, preferably naturally occuring feedstock, therefore said nonionic surfactants comprise acyl units having the formula:
- acyl unit is derived from a source of triglyceride selected from the group consisting of tallow, partially hydrogenated tallow, lard, coconut oil, partially hydrogenated coconut oil, palm kernel oil, hydrogenated palm kernel oil, canola oil, partially hydrogenated canola oil, safflower oil, partially hydrogenated safflower oil, peanut oil, partially hydrogenated peanut oil, sunflower oil, partially hydrogenated sunflower oil, corn oil, partially hydrogenated corn oil, soybean oil, partially hydrogenated soybean oil, tall oil, partially hydrogenated tall oil, rice bran oil, partially hydrogenated rice bran oil, and mixtures thereof.
- tallow partially hydrogenated tallow, lard, coconut oil, partially hydrogenated coconut oil, palm kernel oil, hydrogenated palm kernel oil, canola oil, partially hydrogenated canola oil, safflower oil, partially hydrogenated safflower oil, peanut oil, partially hydrogenated peanut oil, sunflower oil, partially hydrogenated sunflower oil, corn oil, partially hydrogenated corn oil, soybean oil, partially hydrogenated soybean oil, tall
- triglyceride for the acyl unit are synthetic triglyceride feedstocks, for example, triglycerides which are prepared via chemical reaction or other process rather than being derived from a natural source. More preferred feedstocks for said acyl units are tallow, partially hydrogenated tallow, coconut oil, partially hydrogenated coconut oil, canola oil, hydrogenated canola oil, synthetic triglycerides, and mixtures thereof.
- a preferred triglyceride source is tri-oleyl triglycerides.
- R 1 is ethylene;
- R 2 is selected from C3-C4 linear alkyl, C3-C4 branched alkyl, and mixtures thereof; preferably R is 1 ,2-propylene.
- Nonionic surfactants which comprise a mixture of R 1 and R2 units preferably comprise from about 4 to about 12 ethylene units in combination with from about 1 to about 4 1 ,2-propylene units. The units may be alternating, or grouped together in any combination suitable to the formulator.
- the ratio of R1 units to R 2 units is from about 4 : 1 to about 8 : 1.
- an R 2 units i.e. 1 ,2-propylene
- R 3 is selected from hydrogen, C1-C4 linear alkyl, C3-C4 branched alkyl, and mixtures thereof; preferably hydrogen or methyl, more preferably hydrogen.
- R4 is selected from hydrogen, C-1-C4 linear alkyl, C3-C4 branched alkyl, and mixtures thereof; preferably hydrogen.
- index m is equal to 2
- index n must be equal to 0 and the R ⁇ unit is absent and is instead replaced by a - [(R 1 O) x (R2 ⁇ )yR 3 ] unit.
- A is N — (R5) —
- R 5 is selected from -[(R 1 O) x (R 2 O) y ] unit, C1-C16 linear alkyl, C «
- the index m is 1 or 2
- the index n is 0 or 1 , provided that when m is equal to 1 , n is equal to 1 ; and when m is 2 n is 0; preferably m is equal to 2 and n is equal to 0, resulting in two -[(R 1 O) x (R 2 O) y R 3 ] unit and R 4 being absent.
- the index x is from 0 to about 50, preferably from about 1 to about 25, more preferably from about 3 to about 10.
- the index y is from 0 to about 10, preferably 0, however when the index y is not equal to 0, y is from 1 to about 4.
- Preferably all of the alkyleneoxy units are ethyleneoxy units.
- indices x and y are average values and the true values may range over several values depending upon the process used to alkoxylate the amines.
- the index q is 0 or 1.
- Polyoxyalkylene alkylamines are available under various trade names from several suppliers. Representative examples include: Ethomeen, Ethoduomeen from Akzo Chemicals, and/or Secomine from Stepan.
- the polyoxyalkylene alkylamine surface active agents are typically present at levels of from 0.001% to 20% by weight, preferably from 0.5% to 12% by weight, more preferably from 1% to 8% by weight of the composition.
- Preferred among the scum reducing agent herein described are the water- soluble cationic surface active agents.
- the polyamino-functional polymer as described above is the sole nitrogen containing compounds, that the scum reducing agent and the polymer are present in weight ratios of 0.02:1 to 2:1 , preferably 0.05:1 to 1.5:1 , most preferably from 0.1 :1 to 0.8:1.
- the dye fixing agent is the sole nitrogen containing compounds, it has been found preferred to have, for optimum scum reduction, a weight ratio of scum reducing agent to dye fixing of 0.05:1 to 5:1 , more preferably 0.1 :1 to 2.5:1 , most preferably from 0.5:1 to 1 :1.
- a weight ratio of scum reducing agent to the sum of polyamino-functional polymer and dye fixing agents of from 0.05:1 to 2:1 , preferably from 0.1 :1 to 1 :1.
- Fabric softening compound Typical levels of incorporation of the softening compound in the composition are of from 1% to 80% by weight, preferably from 5% to 75%, more preferably from 15% to 70%, and even more preferably from 19% to 65%, by weight of the composition.
- Typical of the cationic softening components are the quaternary ammonium compounds or amine precursors thereof as defined hereinafter.
- A)-Quatemarv Ammonium Fabric Softening Active Compound (1) Preferred quaternary ammonium fabric softening active compound have the formula
- each R unit is independently hydrogen, C ⁇ -CQ alkyl, C-
- An example of a preferred fabric softener active is a mixture of quaternized amines having the formula:
- R is preferably methyl;
- R1 is a linear or branched alkyl or alkenyl chain comprising at least 11 atoms, preferably at least 15 atoms.
- the unit -O2CR ' ' represents a fatty acyl unit which is typically derived from a triglyceride source.
- the triglyceride source is preferably derived from tallow, partially hydrogenated tallow, lard, partially hydrogenated lard, vegetable oils and/or partially hydrogenated vegetable oils, such as, canola oil, safflower oil, peanut oil, sunflower oil, corn oil, soybean oil, tall oil, rice bran oil, etc. and mixtures of these oils.
- the preferred fabric softening actives of the present invention are the Diester and/or Diamide Quaternary Ammonium (DEQA) compounds, the diesters and diamides having the formula:
- R, R 1 , X, and n are the same as defined herein above for formulas (1) and (2), and Q has the formula:
- R is preferably methyl, Q and R 1 are as defined herein before; followed by quaternization to the final softener active.
- preferred amines which are used to. form the DEQA fabric softening actives according to the present invention include methyl bis(2- hydroxyethyl)amine having the formula:
- the counterion, ⁇ ( ⁇ ) above can be any softener-compatible anion, preferably the anion of a strong acid, for example, chloride, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and the like, more preferably chloride or methyl sulfate.
- the anion can also, but less preferably, carry a double. charge in which case ⁇ ( " ) represents half a group.
- Tallow and canola oil are convenient and inexpensive sources of fatty acyl units which are suitable for use in the present invention as R1 units.
- R1 units which are suitable for use in the present invention as R1 units.
- the following are non-limiting examples of quaternary ammonium compounds suitable for use in the compositions of the present invention.
- tallowyl indicates the R1 unit is derived from a tallow triglyceride source and is a mixture of fatty acyl units.
- canolyl refers to a mixture of fatty acyl units derived from canola oil.
- N,N-di(tallowyl-oxy-ethyl)-N,N-dimethyl ammonium chloride N,N-di(canolyl-oxy-ethyl)-N,N-dimethyl ammonium chloride;
- N,N-di(2-canolyloxy-2-oxo-ethyl)-N,N-dimethyl ammonium chloride N,N-di(2-tallowyloxyethylcarbonyloxyethyl)-N,N-dimethyl ammonium chloride;
- quaternay ammoniun softening compounds are methylbis(tallowamidoethyl)(2-hydroxyethyl)ammonium methylsulfate and methylbis(hydrogenated tallowamidoethyl)(2-hydroxyethyl)ammonium methylsulfate; these materials are available from Witco Chemical Company under the trade names Varisoft® 222 and Varisoft® 110, respectively.
- N,N-di(tallowoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride where the tallow chains are at least partially unsaturated.
- the level of unsaturation contained within the tallow, canola, or other fatty acyl unit chain can be measured by the Iodine Value (IV) of the corresponding fatty acid, which in the present case should preferably be in the range of from 5 to 100 with two categories of compounds being distinguished, having a IV below or above 25.
- IV Iodine Value
- fabric softener actives are derived from fatty acyl groups wherein the terms “tallowyl” and canolyl” in the above examples are replaced by the terms “cocoyl, palmyl, lauryl, oleyl, ricinoleyl, stearyl, palmityl,” which correspond to the triglyceride source from which the fatty acyl units are derived.
- These alternative fatty acyl sources can comprise either fully saturated, or preferably at least partly unsaturated chains.
- R units are preferably methyl, however, suitable fabric softener actives are described by replacing the term "methyl” in the above examples in Table II with the units "ethyl, ethoxy, propyl, propoxy, isopropyl, butyl, isobutyl and t-butyl.
- the counter ion, X in the examples of Table II can be suitably replaced by bromide, methyls u If ate, formate, sulfate, nitrate, and mixtures thereof, in fact, the anion, X, is merely present as a counterion of the positively charged quaternary ammonium compounds.
- the scope of this invention is not considered limited to any particular anion.
- the pH of the compositions herein is an important parameter of the present invention. Indeed, it influences the stability of the quaternary ammonium or amine precursors compounds, especially in prolonged storage conditions.
- the pH is measured in the neat compositions at 20 °C. While these compositions are operable at pH of less than about 6.0, for optimum hydrolytic stability of these compositions, the neat pH, measured in the above-mentioned conditions, must preferably be in the range of from about 2.0 to about 5, preferably in the range of 2.5 to 4.5, preferably about 2.5 to about 3.5.
- compositions herein can be regulated by the addition of a
- Suitable acids include the inorganic mineral acids, carboxylic acids, in particular the low molecular weight (C-1-C5) carboxylic acids, and alkylsulfonic acids.
- suitable inorganic acids include HCI, H2SO4, HNO3 and H3PO4.
- Suitable organic acids include formic, acetic, citric, methylsulfonic and ethylsulfonic acid.
- Preferred acids are citric, hydrochloric, phosphoric, formic, methylsulfonic acid, and benzoic acids.
- the diester when specified, it will include the monoester that is normally present in manufacture. For softening, under no/low detergent carry-over laundry conditions the percentage of monoester should be as low as possible, preferably no more than about 2.5%. However, under high detergent carry-over conditions, some monoester is preferred.
- the overall ratios of diester to monoester are from about 100:1 to about 2:1 , preferably from about 50:1 to about 5:1 , more preferably from about 13:1 to about 8:1. Under high detergent carry-over conditions, the di/monoester ratio is preferably about 11 :1.
- the level of monoester present can be controlled in the manufacturing of the softener compound.
- R 4 is an acyclic aliphatic C8-C22 hydrocarbon group
- R5 is a C1-C4 saturated alkyl or hydroxyalkyl group
- R ⁇ is selected from the group consisting of R 4 and R ⁇ groups
- A- is an anion defined as above;
- n is equal to 1 to about 5, and R 1 , R2, R5 and A " are as defined above; (iii) mixtures thereof.
- Examples of the above class cationic nitrogenous salts are the well-known dialkyldi methylammonium salts such as ditallowdimethylammonium chloride, ditallowdimethylammonium methylsulfate, di(hydrogenatedtallow)dimethylammonium chloride, distearyldimethylammonium chloride, dibehenyldimethylammonium chloride. Di(hydrogenatedtallow)di methylammonium chloride and ditallowdimethylammonium chloride are preferred.
- dialkyldimethyl ammonium salts examples include di(hydrogenatedtallow)dimethylammonium chloride (trade name Adogen® 442), ditallowdimethylammonium chloride (trade name Adogen® 470, Praepagen® 3445), distearyl dimethylammonium chloride (trade name Arosurf® TA-100), all available from Witco Chemical Company.
- Dibehenyldimethylammonium chloride is sold under the trade name Kemamine Q-2802C by Humko Chemical Division of Witco Chemical Corporation.
- Dimethylstearylbenzyl ammonium chloride is sold under the trade names Varisoft ® SDC by Witco Chemical Company and Ammonyx® 490 by Onyx Chemical Company.
- Suitable amine fabric softening compounds for use herein, which may be in amine form or cationic form are selected from:
- the preferred Component (i) is a nitrogenous compound selected from the group consisting of the reaction product mixtures or some selected components of the mixtures.
- One preferred component (i) is a compound selected from the group consisting of substituted imidazoline compounds having the formula:
- R is an acyclic aliphatic C-15-C21 hydrocarbon group and R ⁇ is a divalent C1-C3 alkylene group.
- Component (i) materials are commercially available as: Mazamide® 6, sold by Mazer Chemicals, or Ceranine® HC, sold by Sandoz Colors & Chemicals; stearic hydroxyethyl imidazoline sold under the trade names of Alkazine® ST by Alkaril Chemicals, Inc., or Schercozoline® S by Scher Chemicals, Inc.; N,N"- ditallowalkoyldiethylenetriamine; 1 -tallowamidoethyl-2-tallowimidazoline (wherein in the preceding structure R 1 is an aliphatic C15-C-J7 hydrocarbon group and R 3 is a divalent ethylene group).
- compositions (i) can also be first dispersed in a Bronsted acid dispersing aid having a pKa value of not greater than about 4; provided that the pH of the final composition is not greater than about 6.
- a Bronsted acid dispersing aid having a pKa value of not greater than about 4; provided that the pH of the final composition is not greater than about 6.
- Some preferred dispersing aids are hydrochloric acid, phosphoric acid, or methylsulfonic acid.
- N,N"-ditallowalkoyldiethylenetriamine and 1-tallow(amidoethyl)-2- tallowimidazoline are reaction products of tallow fatty acids and diethylenetriamine, and are precursors of the cationic fabric softening agent methyl-1-tallowamidoethyl-2-tallowimidazolinium methylsulfate (see "Cationic Surface Active Agents as Fabric Softeners," R. R. Egan, Journal of the American Oil Chemicals' Society, January 1978, pages 118-121).
- N,N"-ditallow alkoyldiethylenetriamine and 1-tallowamidoethyl-2-tallowimidazoline can be obtained from Witco Chemical Company as experimental chemicals.
- Methyl-1- tallowamidoethyl-2-tallowimidazolinium methylsulfate is sold by Witco Chemical Company under the tradename Varisoft® 475.
- each R2 is a C ⁇ _ ⁇ alkylene group, preferably an ethylene group; and G is an oxygen atom or an -NR- group; and each R, R-' , R 2 and R have the definitions given above and A " has the definitions given above for X " .
- An example of Compound (ii) is 1-oleylamidoethyl-2-oleylimidazolinium chloride wherein R ⁇ is an acyclic aliphatic C15-C17 hydrocarbon group, R2 is an ethylene group, G is a NH group, R is a methyl group and A " is a chloride anion.
- (iii)- softener having the formula:
- R, R1 , R2, and A are defined as above.
- Compound (iii) is the compound having the formula:
- softening active can also encompass mixed softening active agents.
- Preferred among the classes of softener compounds disclosed herein before are the diester or diamido quaternary ammonium fabric softening active compound (DEQA).
- DEQA diester or diamido quaternary ammonium fabric softening active compound
- Fully formulated fabric care compositions may contain, in addition to the hereinbefore described components, one or more of the following ingredients.
- the liquid carrier employed in the instant compositions is preferably at least primarily water due to its low cost, relative availability, safety, and environmental compatibility.
- the level of water in the liquid carrier is preferably at least about 50%, most preferably at least about 60%, by weight of the carrier.
- Mixtures of water and low molecular weight, e.g., ⁇ about 200, organic solvent, e.g., lower alcohols such as ethanol, propanol, isopropanol or butanol are useful as the carrier liquid.
- Low molecular weight alcohols include monohydric, dihydric (glycol, etc.) trihydric (glycerol, etc.), and higher polyhydric (polyols) alcohols.
- compositions of the present invention may comprise one or more solvents which provide increased ease of formulation.
- ease of formulation solvents are all disclosed in WO 97/03169. This is particularly the case when formulating liquid, clear fabric softening compositions.
- the ease of formulation solvent system preferably comprises less than about 40%, preferably from about 10% to about 35%, more preferably from about 12% to about 25%, and even more preferably from about 14% to about 20%, by weight of the composition.
- the ease of formulation solvent is selected to minimize solvent odor impact in the composition and to provide a low viscosity to the final composition.
- isopropyl alcohol is not very effective and has a strong odor.
- n-Propyl alcohol is more effective, but also has a distinct odor.
- butyl alcohols also have odors but can be used for effective clarity/stability, especially when used as part of a ease of formulation solvent system to minimize their odor.
- the alcohols are also selected for optimum low temperature stability, that is they are able to form compositions that are liquid with acceptable low viscosities and translucent, preferably clear, down to about 40°F (about 4.4°C) and are able to recover after storage down to about 20°F (about 6.7°C).
- any ease of formulation solvent for the formulation of the liquid, concentrated, preferably clear, fabric softener compositions herein with the requisite stability is surprisingly selective.
- Suitable solvents can be selected based upon their octanol/water partition coefficient (P) as defined in WO 97/03169.
- P octanol/water partition coefficient
- the ease of formulation solvents herein are selected from those having a ClogP of from about 0.15 to about 0.64, preferably from about 0.25 to about 0.62, and more preferably from about 0.40 to about 0.60, said ease of formulation solvent preferably being at least somewhat asymmetric, and preferably having a melting, or solidification, point that allows it to be liquid at, or near room temperature.
- Solvents that have a low molecular weight and are biodegradable are also desirable for some purposes.
- compositions that have been diluted to the concentration used in the rinse.
- dilute compositions appear to have dispersions of fabric softener that exhibit a more unilamellar appearance than conventional fabric softener compositions. The closer to uni-lamellar the appearance, the better the compositions seem to perform.
- These compositions provide surprisingly good fabric softening as compared to similar compositions prepared in the conventional way with the same fabric softener active.
- ClogP values which fall within the requisite range. These include mono-ols, C6 diols, C7 diols, octanediol isomers, butanediol derivatives, trimethylpentanediol isomers, ethylmethylpentanediol isomers, propyl pentanediol isomers, dimethylhexanediol isomers, ethylhexanediol isomers, methylheptanediol isomers, octanediol isomers, nonanediol isomers, alkyl glyceryl ethers, di(hydroxy alkyl) ethers, and aryl glyceryl ethers, aromatic glyceryl ethers, alicyclic diols and derivatives, C3C7 diol alkoxylated derivatives, aromatic diols,
- Particularly preferred ease of formulation solvents include hexanediols such as 1 ,2-Hexanediol and 2-Ethyl-1 ,3-hexanediol and pentanediols such as 2,2,4-Trimethyl-1 ,3-pentanediol.
- compositions containing both saturated and unsaturated diester quaternary ammonium compounds can be prepared that are stable without the addition of concentration aids.
- the compositions of the present invention may require organic and/or inorganic concentration aids to go to even higher concentrations and/or to meet higher stability standards depending on the other ingredients.
- concentration aids which typically can be viscosity modifiers may be needed, or preferred, for ensuring stability under extreme conditions when particular softener active levels are used.
- the surfactant concentration aids are typically selected from the group consisting of (1) single long chain alkyl cationic surfactants; (2) nonionic surfactants; (3) amine oxides; (4) fatty acids; and (5) mixtures thereof.
- the total level is from 2% to 25%, preferably from 3% to 17%, more preferably from 4% to 15%, and even more preferably from 5% to 13% by weight of the composition.
- These materials can either be added as part of the active softener raw material, (I), e.g., the fatty acid which are reactants used to form the biodegradable fabric softener active as discussed hereinbefore, or added as a separate component.
- the total level of dispersibility aid includes any amount that may be present as part of component
- Inorganic viscosity/dispersibility control agents which can also act like or augment the effect of the surfactant concentration aids, include water-soluble, ionizable salts which can also optionally be incorporated into the compositions of the present invention.
- ionizable salts can be used. Examples of suitable salts are the halides of the Group IA and MA metals of the Periodic Table of the Elements, e.g., calcium chloride, magnesium chloride, sodium chloride, potassium bromide, and lithium chloride.
- the ionizable salts are particularly useful during the process of mixing the ingredients to make the compositions herein, and later to obtain the desired viscosity.
- the amount of ionizable salts used depends on the amount of active ingredients used in the compositions and can be adjusted according to the desires of the formulator. Typical levels of salts used to control the composition viscosity are from about 20 to about 20,000 parts per million (ppm), preferably from about 20 to about 11 ,000 ppm, by weight of the composition.
- Alkylene polyammonium salts can be incorporated into the composition to give viscosity control in addition to or in place of the water-soluble, ionizable salts above.
- these agents can act as scavengers, forming ion pairs with anionic detergent carried over from the main wash, in the rinse, and on the fabrics, and may improve softness performance. These agents may stabilize the viscosity over a broader range of temperature, especially at low temperatures, compared to the inorganic electrolytes.
- alkylene polyammonium salts include l-lysine monohydrochloride and 1 ,5-diammonium 2-methyl pentane dihydrochloride.
- Stabilizers can be present in the compositions of the present invention.
- the term "stabilizer,” as used herein, includes antioxidants and reductive agents. These agents are present at a level of from 0% to about 2%, preferably from about 0.01 % to about 0.2%, more preferably from about 0.035% to about 0.1 % for antioxidants, and more preferably from about 0.01 % to about 0.2% for reductive agents. These assure good odor stability under long term storage conditions for the compositions and compounds stored in molten form.
- the use of antioxidants and reductive agent stabilizers is especially critical for low scent products (low perfume).
- antioxidants examples include a mixture of ascorbic acid, ascorbic palmitate, propyl gallate, available from Eastman Chemical Products, Inc., under the trade names Tenox® PG and Tenox S-1 ; a mixture of BHT (butylated hydroxytoluene), BHA (butylated hydroxyanisole), propyl gallate, and citric acid, available from Eastman Chemical Products, Inc., under the trade name Tenox-6; butylated hydroxytoluene, available from UOP Process Division under the trade name Sustane® BHT; tertiary butylhydroquinone, Eastman Chemical Products, Inc., as Tenox TBHQ; natural tocopherols, Eastman Chemical Products, Inc., as Tenox GT-1/GT-2; and butylated hydroxyanisole, Eastman Chemical Products, Inc., as BHA; long chain esters (C8-C22) of gallic acid, e.g., dodecyl gallate, available from Eastman Chemical Products, Inc.
- Irganox® 1035 41484-35-9 Thiodiethylene bis(3,5-di-tert-butyl-4- hydroxyhydrocinnamate
- Irganox® 1098 23128-74-7 N,N'-Hexamethylene bis(3,5-di-tert-butyl-4- hydroxyhydrocinnamamide
- reductive agents examples include sodium borohydride, hypophosphorous acid, Irgafos® 168, and mixtures thereof.
- Soil Release agents are desirably used in fabric softening compositions of the instant invention. Any polymeric soil release agent known to those skilled in the art can optionally be employed in the compositions of this invention. Polymeric soil release agents are characterized by having both hydrophilic segments, to hy- drophilize the surface of hydrophobic fibers, such as polyester and nylon, and hydrophobic segments, to deposit upon hydrophobic fibers and remain adhered thereto through completion of washing and rinsing cycles and, thus, serve as an anchor for the hydrophilic segments. This can enable stains occurring subsequent to treatment with the soil release agent to be more easily cleaned in later washing procedures.
- soil release agents will generally comprise from about 0.01% to about 10.0%, by weight, of the detergent compositions herein, typically from about 0.1% to about 5%, preferably from about 0.2% to about 3.0%.
- soil release agents include the METOLOSE SM100, METOLOSE SM200 manufactured by Shin-etsu Kagaku Kogyo K.K., SOKALAN type of material, e.g., SOKALAN HP-22, available from BASF (Germany), ZELCON 5126 (from Dupont) and MILEASE T (from ICI).
- bactericides used in the compositions of this invention include glutaraldehyde, formaldehyde, 2-bromo-2-nitro-propane-1 , 3-diol sold by Inolex
- the present invention can contain a perfume. Suitable perfumes are disclosed in U.S. Pat. 5,500,138, said patent being incorporated herein by reference.
- perfume includes fragrant substance or mixture of substances including natural (i.e., obtained by extraction of flowers, herbs, leaves, roots, barks, wood, blossoms or plants), artificial (i.e., a mixture of different nature oils or oil constituents) and synthetic (i.e., synthetically produced) odoriferous substances.
- natural i.e., obtained by extraction of flowers, herbs, leaves, roots, barks, wood, blossoms or plants
- artificial i.e., a mixture of different nature oils or oil constituents
- synthetic i.e., synthetically produced
- perfumes are complex mixtures of a plurality of organic compounds.
- perfume ingredients useful in the perfumes of the present invention compositions include, but are not limited to, hexyl cinnamic aldehyde; amyl cinnamic aldehyde; amyl salicylate; hexyl salicylate; terpineol; 3,7-dimethyl-c/s- 2,6-octadien-1-ol; 2,6-dimethyl-2-octanol; 2,6-dimethyl-7-octen-2-ol; 3,7-dimethyl- 3-octanol; 3,7-dimethyl-frans-2,6-octadien-1-ol; 3,7-dimethyl-6-octen-1-ol; 3,7- dimethyl-1 -octanol; 2-methyl-3-(para-tert-butylphenyl)-propionaldehyde; 4-(4- hydroxy-4-methylpentyl)-3-cyclohexene-1-carbox
- fragrance materials include, but are not limited to, orange oil; lemon oil; grapefruit oil; bergamot oil; clove oil; dodecalactone gamma; methyl-2-(2-pentyl-3-oxo-cyclopentyl) acetate; beta-naphthol methylether; methyl-beta-naphthylketone; coumarin; decylaldehyde; benzaldehyde; 4-tert- butylcyclohexyl acetate; alpha, alpha-dimethylphenethyl acetate; methylphenylcarbinyl acetate; Schiffs base of 4-(4-hydroxy-4-methylpentyl)-3- cyclohexene-1-carboxaldehyde and methyl anthranilate; cyclic ethyleneglycol diester of tridecandioic acid; 3,7-dimethyl-2,6-octadiene-1-nitrile; i
- perfume components are geraniol; geranyl acetate; linalool; linalyl acetate; tetrahydrolinalool; citronellol; citronellyl acetate; dihydromyrcenol; dihydromyrcenyl acetate; tetrahydromyrcenol; terpinyl acetate; nopol; nopyl acetate; 2-phenylethanol; 2-phenylethyl acetate; benzyl alcohol; benzyl acetate; benzyl salicylate; benzyl benzoate; styrallyl acetate; dimethylbenzylcarbinol; trichloromethylphenylcarbinyl methylphenylcarbinyl acetate; isononyl acetate; vetiveryl acetate; vetiverol; 2-methyl-3-(p-tert-butylphenyl)-propanal; 2-methyl-3-(
- Suitable solvents, diluents or carriers for perfumes ingredients mentioned above are for examples, ethanol, isopropanol, diethylene glycol, monoethyl ether, dipropylene glycol, diethyl phthalate, triethyl citrate, etc.
- the amount of such solvents, diluents or carriers incorporated in the perfumes is preferably kept to the minimum needed to provide a homogeneous perfume solution.
- Perfume can be present at a level of from 0% to 10%, preferably from 0.1% to 5%, and more preferably from 0.2% to 3%, by weight of the finished composition.
- Fabric softener compositions of the present invention provide improved fabric perfume deposition.
- Perfume ingredients may also be suitably added as releasable fragrances, for example, as pro-perfumes or pro-fragrances as described in U.S. 5,652,205 Hartman et al., issued July 29, 1997 incorporated herein by reference.
- compositions and processes herein can optionally employ one or more enzymes such as lipases, proteases, cellulase, amylases and peroxidases.
- a preferred enzyme for use herein is a cellulase enzyme. Indeed, this type of enzyme will further provide a color care benefit to the treated fabric.
- Cellulases usable herein include both bacterial and fungal types, preferably having a pH optimum between 5 and 9.5. U.S.
- 4,435,307 discloses suitable fungal cellulases from Humicola insolens or Humicola strain DSM1800 or a cellulase 212- producing fungus belonging to the genus Aeromonas, and cellulase extracted from the hepatopancreas of a marine mollusk, Dolabella Auricula Solander. Suitable cellulases are also disclosed in GB-A-2.075.028; GB-A-2.095.275 and DE-OS-2.247.832. CAREZYME® and CELLUZYME® (Novo) are especially useful.
- compositions herein will typically comprise from 0.001% to 5%, preferably 0.01 %-1 % by weight of a commercial enzyme preparation.
- activity units are preferred (e.g. CEVU or cellulase Equivalent Viscosity Units).
- compositions of the present invention can contain cellulase enzymes at a level equivalent to an activity from 0.5 to 1000 CEVU/gram of composition.
- Cellulase enzyme preparations used for the purpose of formulating the compositions of this invention typically have an activity comprised between 1 ,000 and 10,000 CEVU/gram in liquid form, around 1 ,000 CEVU/gram in solid form.
- compositions of the present invention can further contain a crystal growth inhibitor component, preferably an organodiphosphonic acid component, and/or organo monophosphonic acid, incorporated preferably at a level of from 0.01% to 5%, more preferably from 0.1 % to 2% by weight of the compositions.
- a crystal growth inhibitor component preferably an organodiphosphonic acid component, and/or organo monophosphonic acid, incorporated preferably at a level of from 0.01% to 5%, more preferably from 0.1 % to 2% by weight of the compositions.
- organo diphosphonic acid it is meant herein an organo diphosphonic acid which does not contain nitrogen as part of its chemical structure. This definition therefore excludes the organo aminophosphonates, which however may be included in compositions of the invention as heavy metal ion sequestrant components.
- the organo diphosphonic acid is preferably a C1-C4 diphosphonic acid, more preferably a C2 diphosphonic acid, such as ethylene diphosphonic acid, or most preferably ethane 1-hydroxy-1 ,1 -diphosphonic acid (HEDP) and may be present in partially or fully ionized form, particularly as a salt or complex.
- a C1-C4 diphosphonic acid more preferably a C2 diphosphonic acid, such as ethylene diphosphonic acid, or most preferably ethane 1-hydroxy-1 ,1 -diphosphonic acid (HEDP) and may be present in partially or fully ionized form, particularly as a salt or complex.
- HEDP ethane 1-hydroxy-1 ,1 -diphosphonic acid
- crystal growth inhibitor are the organic monophosphonic acid Organo monophosphonic acid or one of its salts or complexes is also suitable for use herein as a CGI.
- organo monophosphonic acid it is meant herein an organo monophosphonic acid which does not contain nitrogen as part of its chemical structure. This definition therefore excludes the organo aminophosphonates, which however may be included in compositions of the invention as heavy metal ion sequestrants.
- the organo monophosphonic acid component may be present in its acid form or in the form of one of its salts or complexes with a suitable counter cation.
- any salts/complexes are water soluble, with the alkali metal and alkaline earth metal salts/complexes being especially preferred.
- a prefered organo monophosphonic acid is 2-phosphonobutane-1 ,2,4- tricarboxylic acid commercially available from Bayer under the tradename of Bayhibit.
- the present invention can include optional components conventionally used in textile treatment compositions, for example: brighteners, colorants; surfactants; anti-shrinkage agents; fabric crisping agents; spotting agents; germicides; fungicides; anti-oxidants such as butylated hydroxy toluene, anti-corrosion agents, antifoam agents, and the like.
- the present invention can also include other compatible ingredients, including those as disclosed in WO96/02625, W096/21714, and W096/21715, and dispersible polyolefin such as Velustrol® as disclosed in co-pending application PCT/US 97/01644, and the like.
- the present invention can also contain optional chelating agents such as ethylenediamine-N,N'-disuccinic acid, (S,S) isomer in the form of its sodium salt (EDDS) and crystal growth inhibitors such as glycolic acid and/or 1 ,1-hydroxyethane diphosphonic acid (HEDP).
- the fabric care composition can take a variety of physical forms including liquid such as aqueous or non-aqueous compositions and solid forms such as solid particulate forms.
- compositions may be applied onto a substrate such as a dryer sheet product, used as a rinse added product, or as a spray or foam product.
- a surface active agent preferably a scum reducing agent as herein before described in a composition comprising a nitrogen containing compound selected from a polyamino-functional polymer, a dye fixing agent, and mixtures thereof, for reducing or preventing the formation of scum on fabrics or washing machine parts contacted with the composition.
- a nitrogen containing compound selected from a polyamino-functional polymer, a dye fixing agent, and mixtures thereof.
- the fabric softening composition can conveniently be made according to well known processes to the skilled person.
- An exemplary disclosure is given in EP- A-0,668,902.
- DEQA Di-(tallowyl-oxy-ethyl) dimethyl ammonium chloride DOEQA Di-(oleyloxyethyl) dimethyl ammonium methylsulfate
- DTDMAC Ditallow dimethylammonium chloride
- DHEQA Di-(soft-tallowyl-oxy-ethyl) hydroxyethyl methyl ammonium methylsulfate
- Glycosperse S-20 Polyethoxylated sorbitan monostearate available from Lonza
- PEI 1800 E1 Ethoxylated polyethylene imine (MW 1800, at 50% active) as synthesised in Synthesis example 1
- PEI 1800 E3 Ethoxylated polyethylene imine (MW 1800, at 50% active) as synthesised as per Synthesis example 1
- PEI 1200 E1 Ethoxylated polyethylene imine (MW 1200, at 50% active in water) as synthesised in Synthesis example 5
- PEI 1200 E2 Ethoxylated polyethylene imine (MW 1200, at 50% active in water) as synthesised per Synthesis example 5
- PEI 1200 E7 Ethoxylated polyethylene imine (MW 1200, at 50% active in water) as synthesised per Synthesis example 5
- Dye Fix 1 Cellulose reactive dye fixing agent available under the tradename Tinofix FRD from Ciba-Geigy
- Dye Fix 2 Cellulose reactive dye fixing agent available under the tradename Rewin DWR from CHT R. Beitlich
- Scum reducing agent 1 N,N dimethyl-N-(2-hydroxyethyl)-N-dodecyl/tetradecyl ammonium bromide
- Scum reducing agent 2 C12/C14 Choline ester
- Ci4_i5 predominantly linear primary alcohol condensed with an average of 7 moles of ethylene oxide
- Na ⁇ 2 (A10 2 Si ⁇ 2)i2- 27H20 having a primary particle size in the range from 0.1 to 10 micrometers
- Citric acid Anhydrous citric acid Carbonate Anhydrous sodium carbonate with a particle size between 200 ⁇ m and 900 ⁇ m
- Silicate Amorphous Sodium Silicate Si ⁇ 2:Na2 ⁇ ; 2.0 ratio
- MA/AA Copolymer of 1:4 maleic/acrylic acid average molecular weight about 70,000.
- Lipolase Lipolytic enzyme of activity 10OkLU/g all sold by NOVO Industries A/S and of activity mentioned above unless otherwise specified
- Silicone antifoam Polydimethyldiloxane foam controller with Siloxane-oxyalkylene copolymer as dispersing agent with a ratio of said foam controller to said dispersing agent of 10:1 to 100:1.
- Bayhibit AM 2-phosphonobutane-1 ,2,4-tricarboxylic acid commercially available from Bayer
- Step A)-The ethoxylation is conducted in a 2 gallon stirred stainless steel autoclave equipped for temperature measurement and control, pressure measurement, vacuum and inert gas purging, sampling, and for introduction of ethylene oxide as a liquid.
- a -20 lb. net cylinder of ethylene oxide (ARC) is set up to deliver ethylene oxide as a liquid by a pump to the autoclave with the cylinder placed on a scale so that the weight change of the cylinder could be monitored.
- a 750 g portion of polyethyleneimine (PEI) (Nippon Shokubai, Epomin SP-018 having a listed average molecular weight of 1800 equating to 0.417 moles of polymer and 17.4 moles of nitrogen functions) is added to the autoclave.
- the autoclave is then sealed and purged of air (by applying vacuum to minus 28" Hg followed by pressurization with nitrogen to 250 psia, then venting to atmospheric pressure).
- the autoclave contents are heated to 130 °C while applying vacuum.
- the autoclave is charged with nitrogen to about 250 psia while cooling the autoclave to about 105 °C.
- Ethylene oxide is then added to the autoclave incrementally over time while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate.
- the ethylepe oxide pump is turned off and cooling is applied to limit any temperature increase resulting from any reaction exotherm.
- the temperature is maintained between 100 and 110 °C while the total pressure is allowed to gradually increase during the course of the reaction.
- Step B)- The reaction mixture is then deodorized by passing about 100 cu. ft. of inert gas (argon or nitrogen) through a gas dispersion frit and through the reaction mixture while agitating and heating the mixture to 130 °C.
- inert gas argon or nitrogen
- the final reaction product is cooled slightly and collected in glass containers purged with nitrogen.
- Step A and B If a PEI 1800 E7 is desired, the following step of catalyst addition will be included between Step A and B.
- Vacuum is continuously applied while the autoclave is cooled to about 50 °C while introducing 376 g of a 25% sodium methoxide in methanol solution (1.74 moles, to achieve a 10% catalyst loading based upon PEI nitrogen functions).
- the methoxide solution is sucked into the autoclave under vacuum and then the autoclave temperature controller setpoint is increased to 130 °C.
- a device is used to monitor the power consumed by the agitator.
- the agitator power is monitored along with the temperature and pressure. Agitator power and temperature values gradually increase as methanol is removed from the autoclave and the viscosity of the mixture increases and stabilizes in about 1 hour indicating that most of the methanol has been removed.
- the mixture is further heated and agitated under vacuum for an additional 30 minutes. Vacuum is removed and the autoclave is cooled to 105 °C while it is being charged with nitrogen to 250 psia and then vented to ambient pressure. The autoclave is charged to 200 psia with nitrogen. Ethylene oxide is again added to the autoclave incrementally as before while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate while maintaining the temperature between 100 and 110 °C and limiting any temperature increases due to reaction exotherm. After the addition of 4500 g of ethylene oxide (resulting in a total of 7 moles of ethylene oxide per mole of PEI nitrogen function) is achieved over several hours, the temperature is increased to 110 °C and the mixture stirred for an additional hour.
- reaction mixture is then collected in nitrogen purged containers and eventually transferred into a 22 L three neck round bottomed flask equipped with heating and agitation.
- the strong alkali catalyst is neutralized by adding 167 g methanesulfonic acid (1.74 moles).
- PEI 1800 E2 PEI 1800 E3, PEI 1800 E15 and PEI 1800 E20 can be prepared by the above method by adjusting the reaction time and the relative amount of ethylene oxide used in the reaction.
- Dimethyl sulfate (Aldrich, 3.8g, 0.030 mol) is added all at once to the rapidly stirring solution, which is then stoppered and stirred at room temperature overnight.
- the resonances ascribed to methylene protons adjacent to unoxidized nitrogens have shifted from the original position at ⁇ 2.5 ppm to ⁇ 3.5 ppm.
- To the reaction solution is added approximately 5 g of 0.5% Pd on alumina pellets, and the solution is allowed to stand at room temperature for approximately 3 days. The solution is tested and found to be negative for peroxide by indicator paper.
- the material as obtained is suitably stored as a
- Step A)-The ethoxylation is conducted in a 2 gallon stirred stainless steel autoclave equipped for temperature measurement and control, pressure measurement, vacuum and inert gas purging, sampling, and for introduction of ethylene oxide as a liquid.
- a ⁇ 20 lb. net cylinder of ethylene oxide (ARC) is set up to deliver ethylene oxide as a liquid by a pump to the autoclave with the cylinder placed on a scale so that the weight change of the cylinder could be monitored.
- a 750 g portion of polyethyleneimine (PEI) (having a listed average molecular weight of 1200 equating to about 0.625 moles of polymer and 17.4 moles of nitrogen functions) is added to the autoclave.
- the autoclave is then sealed and purged of air (by applying vacuum to minus 28" Hg followed by pressurization with nitrogen to 250 psia, then venting to atmospheric pressure).
- the autoclave contents are heated to 130 °C while applying vacuum.
- the autoclave is charged with nitrogen to about 250 psia while cooling the autoclave to about 105 °C.
- Ethylene oxide is then added to the autoclave incrementally over time while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate.
- the ethylene oxide pump is turned off and cooling is applied to limit any temperature increase resulting from any reaction exotherm.
- the temperature is maintained between 100 and 110 °C while the total pressure is allowed to gradually increase during the course of the reaction.
- Step B)- The reaction mixture is then deodorized by passing about 100 cu. ft. of inert gas (argon or nitrogen) through a gas dispersion frit and through the reaction mixture while agitating and heating the mixture to 130 °C.
- inert gas argon or nitrogen
- the final reaction product is cooled slightly and collected in glass containers purged with nitrogen.
- Step A If a PEI 1200 E7 is desired, the following step of catalyst addition will be included between Step A and B.
- Vacuum is continuously applied while the autoclave is cooled to about 50 °C while introducing 376 g of a 25% sodium methoxide in methanol solution (1.74 moles, to achieve a 10% catalyst loading based upon PEI nitrogen functions).
- the methoxide solution is sucked into the autoclave under vacuum and then the autoclave temperature controller setpoint is increased to 130 °C.
- a device is used to monitor the power consumed by the agitator.
- the agitator power is monitored along with the temperature and pressure. Agitator power and temperature values gradually increase as methanol is removed from the autoclave and the viscosity of the mixture increases and stabilizes in about 1 hour indicating that most of the methanol has been removed.
- the mixture is further heated and agitated under vacuum for an additional 30 minutes. Vacuum is removed and the autoclave is cooled to 105 °C while it is being charged with nitrogen to 250 psia and then vented to ambient pressure. The autoclave is charged to 200 psia with nitrogen. Ethylene oxide is again added to the autoclave incrementally as before while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate while . maintaining the temperature between 100 and 110 °C and limiting any temperature increases due to reaction exotherm. After the addition of 4500 g of ethylene oxide (resulting in a total of 7 moles of ethylene oxide per mole of PEI nitrogen function) is achieved over several hours, the temperature is increased to 110 °C and the mixture stirred for an additional hour.
- reaction mixture is then collected in nitrogen purged containers and eventually transferred into a 22 L three neck round bottomed flask equipped with heating and agitation.
- the strong alkali catalyst is neutralized by adding 167 g methanesulfonic acid (1.74 moles).
- PEI 1200 E2, PEI 1200 E3, PEI 1200 E15 and PEI 1200 E20 can be prepared by the above method by adjusting the reaction time and the relative amount of ethylene oxide used in the reaction.
- the corresponding amine oxide of the above ethoxylated PEI can also be prepared following synthesis Example 4.
- Synthesis Example 6 -9.7% Quaternization of PEI 1200 E7
- poly(ethyleneimine) MW 1200 ethoxylated to a degree of 7 (248.4g, 0.707 mol nitrogen, prepared as in Synthesis Example 5)
- acetonitrile Baker, 200 mL.
- Dimethyl sulfate Aldrich, 8.48g, 0.067 mol is added all at once to the rapidly stirring solution, which is then stoppered and stirred at room temperature overnight.
- acetonitrile is evaporated on the rotary evaporator at ⁇ 60°C, followed by a Kugelrohr apparatus (Aldrich) at ⁇ 80°C to afford ⁇ 220g of the desired material as a dark brown viscous liquid.
- a 1 3 C-NMR (D2O) spectrum shows the absence of a peak at ⁇ 58ppm corresponding to dimethyl sulfate.
- a 1 H-NMR (D2O) spectrum shows the partial shifting of the peak at 2.5ppm (methylenes attached to unquaternized nitrogens) to ⁇ 3.0ppm.
- compositions for use as dryer-added sheets are in accordance with the invention.
- detergent formulations S and T are in accordance with the present invention:
- liquid detergent formulation according to the present invention was prepared:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Detergent Compositions (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP98938209A EP1100857B1 (en) | 1998-07-31 | 1998-07-31 | Use of surface active agents to reduce scum in fabric care compositions |
CA002336398A CA2336398A1 (en) | 1998-07-31 | 1998-07-31 | Fabric care compositions |
BR9815974-7A BR9815974A (en) | 1998-07-31 | 1998-07-31 | Compositions for fabric protection |
AU86788/98A AU8678898A (en) | 1998-07-31 | 1998-07-31 | Fabric care compositions |
CZ20010007A CZ302973B6 (en) | 1998-07-31 | 1998-07-31 | Fabric care composition and use thereof |
AT98938209T ATE486924T1 (en) | 1998-07-31 | 1998-07-31 | USE OF SURFACE-ACTIVE SUBSTANCES FOR SCUM REDUCTION IN FABRIC CARE PRODUCTS |
PCT/US1998/015955 WO2000006680A1 (en) | 1998-07-31 | 1998-07-31 | Fabric care compositions |
KR1020017000755A KR20010053561A (en) | 1998-07-31 | 1998-07-31 | Fabric care compositions |
JP2000562464A JP2002521583A (en) | 1998-07-31 | 1998-07-31 | Fabric protection composition |
DE69841985T DE69841985D1 (en) | 1998-07-31 | 1998-07-31 | USE OF SURFACE ACTIVE SUBSTANCES FOR SCUM REDUCTION IN TISSUE DEPOSITS |
ES98938209T ES2355796T3 (en) | 1998-07-31 | 1998-07-31 | USE OF TENSIOACTIVE AGENTS TO REDUCE FOAM IN COMPOSITIONS FOR FABRIC CARE. |
ZA9904687A ZA994687B (en) | 1998-07-31 | 1999-07-21 | Fabric care compositions. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US1998/015955 WO2000006680A1 (en) | 1998-07-31 | 1998-07-31 | Fabric care compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000006680A1 true WO2000006680A1 (en) | 2000-02-10 |
Family
ID=22267609
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1998/015955 WO2000006680A1 (en) | 1998-07-31 | 1998-07-31 | Fabric care compositions |
Country Status (12)
Country | Link |
---|---|
EP (1) | EP1100857B1 (en) |
JP (1) | JP2002521583A (en) |
KR (1) | KR20010053561A (en) |
AT (1) | ATE486924T1 (en) |
AU (1) | AU8678898A (en) |
BR (1) | BR9815974A (en) |
CA (1) | CA2336398A1 (en) |
CZ (1) | CZ302973B6 (en) |
DE (1) | DE69841985D1 (en) |
ES (1) | ES2355796T3 (en) |
WO (1) | WO2000006680A1 (en) |
ZA (1) | ZA994687B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6627591B2 (en) | 1999-12-17 | 2003-09-30 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Dye fixing composition |
JP2015101674A (en) * | 2013-11-26 | 2015-06-04 | ライオン株式会社 | Liquid detergent |
WO2021219351A1 (en) * | 2020-04-28 | 2021-11-04 | Unilever Ip Holdings B.V. | An aqueous laundry treatment composition |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6607686B2 (en) * | 2015-03-26 | 2019-11-20 | ライオン株式会社 | Liquid detergent for textile products |
Citations (5)
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JPS62256899A (en) * | 1986-04-28 | 1987-11-09 | ミヨシ油脂株式会社 | Liquid detergent composition |
US5460736A (en) * | 1994-10-07 | 1995-10-24 | The Procter & Gamble Company | Fabric softening composition containing chlorine scavengers |
WO1995032272A1 (en) * | 1994-05-25 | 1995-11-30 | The Procter & Gamble Company | Compositions comprising ethoxylated/propoxylated polyalkyleneamine polymers as soil dispersing agents |
GB2303146A (en) * | 1995-07-08 | 1997-02-12 | Procter & Gamble | Detergent compositions |
WO1998017758A1 (en) * | 1996-10-18 | 1998-04-30 | The Procter & Gamble Company | Detergent compositions |
-
1998
- 1998-07-31 JP JP2000562464A patent/JP2002521583A/en not_active Withdrawn
- 1998-07-31 WO PCT/US1998/015955 patent/WO2000006680A1/en active IP Right Grant
- 1998-07-31 KR KR1020017000755A patent/KR20010053561A/en active IP Right Grant
- 1998-07-31 AU AU86788/98A patent/AU8678898A/en not_active Abandoned
- 1998-07-31 EP EP98938209A patent/EP1100857B1/en not_active Expired - Lifetime
- 1998-07-31 AT AT98938209T patent/ATE486924T1/en not_active IP Right Cessation
- 1998-07-31 CA CA002336398A patent/CA2336398A1/en not_active Abandoned
- 1998-07-31 DE DE69841985T patent/DE69841985D1/en not_active Expired - Lifetime
- 1998-07-31 CZ CZ20010007A patent/CZ302973B6/en not_active IP Right Cessation
- 1998-07-31 BR BR9815974-7A patent/BR9815974A/en unknown
- 1998-07-31 ES ES98938209T patent/ES2355796T3/en not_active Expired - Lifetime
-
1999
- 1999-07-21 ZA ZA9904687A patent/ZA994687B/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS62256899A (en) * | 1986-04-28 | 1987-11-09 | ミヨシ油脂株式会社 | Liquid detergent composition |
WO1995032272A1 (en) * | 1994-05-25 | 1995-11-30 | The Procter & Gamble Company | Compositions comprising ethoxylated/propoxylated polyalkyleneamine polymers as soil dispersing agents |
US5460736A (en) * | 1994-10-07 | 1995-10-24 | The Procter & Gamble Company | Fabric softening composition containing chlorine scavengers |
GB2303146A (en) * | 1995-07-08 | 1997-02-12 | Procter & Gamble | Detergent compositions |
WO1998017758A1 (en) * | 1996-10-18 | 1998-04-30 | The Procter & Gamble Company | Detergent compositions |
Non-Patent Citations (1)
Title |
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DATABASE WPI Section Ch Week 8750, Derwent World Patents Index; Class D25, AN 87-352690, XP002096170 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6627591B2 (en) | 1999-12-17 | 2003-09-30 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Dye fixing composition |
JP2015101674A (en) * | 2013-11-26 | 2015-06-04 | ライオン株式会社 | Liquid detergent |
WO2021219351A1 (en) * | 2020-04-28 | 2021-11-04 | Unilever Ip Holdings B.V. | An aqueous laundry treatment composition |
CN115362247A (en) * | 2020-04-28 | 2022-11-18 | 联合利华知识产权控股有限公司 | Aqueous laundry treatment composition |
Also Published As
Publication number | Publication date |
---|---|
ES2355796T3 (en) | 2011-03-31 |
BR9815974A (en) | 2001-10-09 |
ZA994687B (en) | 2000-01-31 |
EP1100857A1 (en) | 2001-05-23 |
AU8678898A (en) | 2000-02-21 |
KR20010053561A (en) | 2001-06-25 |
CZ20017A3 (en) | 2002-01-16 |
CZ302973B6 (en) | 2012-02-01 |
ATE486924T1 (en) | 2010-11-15 |
DE69841985D1 (en) | 2010-12-16 |
JP2002521583A (en) | 2002-07-16 |
CA2336398A1 (en) | 2000-02-10 |
EP1100857B1 (en) | 2010-11-03 |
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