EP0547722A1 - Freifliessendes wäscheweichmachendes Pulver und Verfahren zu seiner Herstellung - Google Patents
Freifliessendes wäscheweichmachendes Pulver und Verfahren zu seiner Herstellung Download PDFInfo
- Publication number
- EP0547722A1 EP0547722A1 EP92203997A EP92203997A EP0547722A1 EP 0547722 A1 EP0547722 A1 EP 0547722A1 EP 92203997 A EP92203997 A EP 92203997A EP 92203997 A EP92203997 A EP 92203997A EP 0547722 A1 EP0547722 A1 EP 0547722A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- water
- weight
- softening
- cationic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 58
- 239000004744 fabric Substances 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000000843 powder Substances 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 239000002002 slurry Substances 0.000 claims abstract description 27
- 239000002245 particle Substances 0.000 claims abstract description 26
- 239000003599 detergent Substances 0.000 claims abstract description 23
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004202 carbamide Substances 0.000 claims abstract description 12
- 239000006185 dispersion Substances 0.000 claims abstract description 12
- 125000000129 anionic group Chemical group 0.000 claims abstract description 10
- 238000001694 spray drying Methods 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 239000007921 spray Substances 0.000 claims abstract description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
- 239000000194 fatty acid Substances 0.000 claims description 12
- 229930195729 fatty acid Natural products 0.000 claims description 12
- 150000004665 fatty acids Chemical class 0.000 claims description 12
- 125000002091 cationic group Chemical group 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 8
- 229940098691 coco monoethanolamide Drugs 0.000 claims description 3
- 150000001767 cationic compounds Chemical class 0.000 claims description 2
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 claims description 2
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 claims description 2
- 239000004902 Softening Agent Substances 0.000 claims 1
- -1 cationic quaternary ammonium compound Chemical class 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000007788 liquid Substances 0.000 description 11
- 239000002979 fabric softener Substances 0.000 description 8
- 150000002191 fatty alcohols Chemical class 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 8
- 239000003945 anionic surfactant Substances 0.000 description 7
- 239000003760 tallow Substances 0.000 description 6
- 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 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 150000004996 alkyl benzenes Chemical class 0.000 description 5
- 239000004665 cationic fabric softener Substances 0.000 description 5
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000344 soap Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 description 4
- 150000003871 sulfonates Chemical class 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000001143 conditioned effect Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 150000004668 long chain fatty acids Chemical class 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 230000000153 supplemental effect Effects 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 0 *C(N*=C)=O Chemical compound *C(N*=C)=O 0.000 description 1
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
- ILEZQQBGPUFNQT-UHFFFAOYSA-M 2-[1-(4-chlorobutyl)-2-heptadec-1-enyl-4,5-dihydroimidazol-1-ium-1-yl]ethanol;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC=CC1=NCC[N+]1(CCO)CCCCCl ILEZQQBGPUFNQT-UHFFFAOYSA-M 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- UFQDKRWQSFLPQY-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-3-ium;chloride Chemical compound Cl.C1CN=CN1 UFQDKRWQSFLPQY-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- CDBJBDCGBLHNGX-UHFFFAOYSA-M [Cl-].C(=CCCCCCCCCCCCCCCC)C=1[N+](CCN1)(CC1=CC=CC=C1)CCO Chemical compound [Cl-].C(=CCCCCCCCCCCCCCCC)C=1[N+](CCN1)(CC1=CC=CC=C1)CCO CDBJBDCGBLHNGX-UHFFFAOYSA-M 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000004945 acylaminoalkyl group Chemical group 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- ZZWIVBDHVZYXJT-UHFFFAOYSA-L dihexadecyl(dimethyl)azanium dimethylazanium dimethyl(dioctadecyl)azanium bromide dichloride Chemical compound [Br-].C(CCCCCCCCCCCCCCCCC)[N+](C)(C)CCCCCCCCCCCCCCCCCC.[Cl-].C(CCCCCCCCCCCCCCC)[N+](C)(C)CCCCCCCCCCCCCCCC.[Cl-].C[NH2+]C ZZWIVBDHVZYXJT-UHFFFAOYSA-L 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- BYMDYVGMUOWHBE-UHFFFAOYSA-M ethyl sulfate;2-(2-heptadecyl-1-octadecyl-4,5-dihydroimidazol-1-ium-1-yl)ethanol Chemical compound CCOS([O-])(=O)=O.CCCCCCCCCCCCCCCCCC[N+]1(CCO)CCN=C1CCCCCCCCCCCCCCCCC BYMDYVGMUOWHBE-UHFFFAOYSA-M 0.000 description 1
- 125000000373 fatty alcohol group Chemical group 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- FFJMLWSZNCJCSZ-UHFFFAOYSA-N n-methylmethanamine;hydrobromide Chemical compound Br.CNC FFJMLWSZNCJCSZ-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011347 resin Chemical class 0.000 description 1
- 229920005989 resin Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 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
- C11D1/65—Mixtures of anionic with cationic compounds
- C11D1/652—Mixtures of anionic compounds with carboxylic amides or alkylol amides
-
- 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
- C11D1/65—Mixtures of anionic with cationic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/835—Mixtures of non-ionic with cationic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/86—Mixtures of anionic, cationic, and non-ionic 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
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/02—Preparation in the form of powder by spray drying
-
- 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
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
- C11D3/323—Amides; Substituted amides urea or derivatives thereof
-
- 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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
Definitions
- This invention relates to a free-flowing, spray-dried concentrated particulate fabric softening composition which is readily dispersible in water and to a process for its manufacture and use. More particularly, the present invention relates to an effective fabric softening composition in a form which is convenient for use, capable of containing a relatively high proportion of cationic fabric softener, and can be economically packaged and shipped.
- Fabric softening or conditioning compositions for use in household washing machines are marketed extensively in the United States and Europe.
- these compositions are aqueous liquids containing as the principal active ingredient a cationic quaternary ammonium compound to impart a softening effect to fabrics treated therewith in the laundry bath.
- these fabric softeners (the common designation for such softening compositions) contain from about 5 to 8% of the active cationic softening compound.
- a United States washing machine containing about 65 liters of water, normally about 90 grams of a 6% active liquid fabric softener is added to the rinse cycle to achieve an acceptable softening level.
- Liquid fabric softeners have certain inherent disadvantages.
- the level of the active cationic quaternary ammonium compound capable of being introduced into an aqueous system is generally limited by properties of solubility of the quaternary compound and stability and pourability of the final product.
- Conventional rinse-added fabric softening compositions contain quaternary ammonium compounds, typically having two long alkyl chains, which are substantially water-insoluble materials.
- the softening compositions are, therefore, normally in the form of an aqueous dispersion or emulsion. Consequently, at higher concentrations of the active cationic softening compound, generally above about 6%, by weight, problems in product formulation, stability (i.e. product separation), gel-formation and water dispersibility are likely to occur.
- concentrations above about 9%, by weight, of quaternary ammonium compounds the viscosity and stability of the aqueous liquid softener are often unacceptable for commercial purposes.
- a process for preparing a powdered quaternary softener wherein a solution of the quaternary ammonium compound is sprayed onto a particulate carrier, such as urea or sodium tripolyphosphate, so as to provide particles of carrier having a coating of the softener.
- a particulate carrier such as urea or sodium tripolyphosphate
- U.S. Patent 4,427,558 to David discloses fabric softening particles comprised of a quaternary ammonium compound, urea, and a calcium soap such as calcium tallow soap.
- the process of preparation comprises forming a liquid mixture of the desired components, cooling the liquid to form a solid and then grinding to form particles. Prior to grinding, the solid is “weathered” for several hours, the term “weathering” being used to describe the process of allowing the water content of the particles to approach equilibrium with the environment. Particles may also be formed, according to the disclosure, by "spray cooling" a liquid mixture whereby a solid is formed with no accompanying loss of water. The resulting solid is then ground and weathered.
- EP 1315 Procter & Gamble
- molten particles of a quaternary ammonium compound and a dispersion inhibitor such as a fatty alcohol or fatty acid are attached to spray-dried base detergent granules containing surfactant and builder.
- a dispersion inhibitor such as a fatty alcohol or fatty acid
- a highly concentrated particulate fabric softening composition can be prepared in accordance with the invention by a spray drying process which provides particles of a softening composition containing up to about 40% of a cationic softening compound in combination with a nonionic and/or an anionic surfactant, among other components, which particles are readily dispersible in water and provide effective softening.
- the present invention provides a free-flowing spray-dried particulate fabric softening composition which is readily dispersible in water comprising:
- composition further contains from about 1 to 10%, by weight, of a fatty acid alkanolamide.
- the invention also encompasses a process of producing a free-flowing spray-dried particulate fabric softening composition which is readily dispersible in water comprising:
- the invention is predicated on the discovery that a fabric softening composition can be prepared in particulate form by spray drying to provide a composition more highly concentrated than conventional liquid rinse-cycle softeners.
- the resulting spray dried particles are dispersible in water and provide effective softening to fabrics in a wash or rinse cycle aqueous bath.
- An essential feature of the composition of the invention is that uniform spray dried particles are formed by utilizing a mixing step prior to spray drying the crutcher slurry such that the contents of the crutcher slurry are thoroughly dispersed and form a mixture or dispersion having an average particle size of below about 1.0 micron.
- Uniform mixtures of this type may be achieved with various types of mixers, mills or pumps known in the art, but it is preferred to use a so-called "homogenizer” such as a Gaulin Homogenizer marketed by Gaulin Corporation of Everett, Massachusetts, U.S.A. or Hilversum, Holland, which consists essentially of a positive displacement pump to which is attached a homogenizing valve assembly capable of providing an intimate mixture having an average particle size diameter of below about 1.0 microns, and more preferably below about 0.75 microns.
- the preferred maximum size of particles in such mixture is below about 5.0 microns and more preferably below about 3.0 microns.
- the process of spray drying a softening composition in accordance with the invention utilizes, for the most part, well known technology relating to the production of particulate detergent compositions.
- an aqueous crutcher slurry is formed containing a mixture of water with many or most of the ingredients desired in the fabric softening composition.
- the solids content of the slurry is generally from about 20% to about 70%, preferably 30% to 60%, and most preferably from 40% to 50% thereof, the balance being water.
- the crutcher slurry is then atomized by pumping it an atomizing nozzle at a pressure of about 1000 to 2000 psi into a spray-drying tower, the typical dimensions of a commercial tower being about 35-100 feet in height and about 12-30 feet in diameter.
- air is introduced at a temperature of from about 300-1000°F which contacts the atomized slurry to provide a hot drying gas for the droplets of the slurry thereby evaporating most of the water.
- the resulting particles or beads are collected at the bottom of the tower, the moisture and heated air existing at the top.
- Heat or water-sensitive ingredients such as perfume may be post-added to the tower particles in a subsequent mixing or blending operation.
- the crutcher slurry is preferably made by sequentially adding the various components thereof in the manner which will result in the most miscible and readily pumpable slurry for spray drying.
- the order of addition of the various components may be varied, depending on the circumstances. Normally, it is preferable for all or almost all of the water to be added to the crutcher first, preferably at about the processing temperature, after which the other components are added in sequence namely, urea, the quaternary ammonium softening compound, anionic and/or nonionic surfactants, a fatty acid alkanolamides and optionally adjuvants, such as pigments, anti-oxidants and germicides.
- the temperature of the aqueous medium in the crutcher will usually be about room temperature or elevated, normally being in the 20 to 70°C range, and preferably from about 25 to 40°C.
- crutcher mixing times to obtain thoroughly mixed homogeneous slurries can vary widely, from as little as five minutes in small crutchers and for slurries of higher moisture contents, to as much as one hour, in some cases, although 30 minutes is a preferable upper limit.
- the crutcher slurry is transferred for further mixing to a "homogenizer" or similar mixer or pump to obtain the uniform dispersion or mixture described above having an average particle size of below about 1.0 micron.
- the resulting dispersion is thereafter transferred in the usual manner to a spray drying tower, which is located near the crutcher.
- the dispersion is forced at high pressure through spray nozzles into the spray tower (countercurrent or concurrent), wherein the droplets of the slurry fall through a hot drying gas to form particles or beads of the fabric softening composition while evaporating substantially all the water.
- the moisture content of the particles is preferably about 2 to 4%, by weight.
- the cationic quaternary ammonium softening compounds useful for the invention include imidazolinium salts, di-long chain alkyl quaternary ammonium salts and diesterified long chain fatty acid dilower alkyl quaternary ammonium salts.
- R1 is a C8 to C30 aliphatic radical and preferably a C14 to C18 alkyl or alkenyl
- R2 and R3 independently may be any of R1 or preferably, lower alkyl or substituted alkyl of C1 to C4 such as haloalkyl, hydroxyalkyl, acylaminoalkyl and the like
- X is a water-solubilizing anion such as chloride, bromide, iodide, fluoride, sulfate, methosulfate, nitrite, nitrate, phosphate and carboxylate, (e.g.
- Typical imidazolinium softening compounds include: 2-heptadecyl-1-methyl-1-oleylamidoethyl imidazolinium ethosulfate 2-heptadecyl-1-methyl-1-(2-stearoylamido)ethyl - imidazolinium sulfate, 2-heptadecyl-1-methyl-1-(2-stearoylamido)ethyl - imidazolinium chloride, 2-coco-1-(2-hydroxyethyl)-1-benzyl imidazolinium chloride, 2-coco-1-(hydroxyethyl)-1-(4-chlorobutyl) imidazolinium chloride, 2-coco-1-(2-hydroxyethyl)-1-octadecenyl imidazolinium chloride, 2-tall oil fatty-1-(2-hydroxyethyl)-1-benzy
- R groups are selected from C1 to C30 aliphatic, preferably alkyl or alkenyl; aryl (e.g. phenyl, toloyl, cumyl, etc.); aralkyl (e.g. benzyl, phenethyl, methylbenzyl, etc.); and the halo, amide, hydroxyl, and carboxy sustituents thereof such as halo C2 to C6 alkyl (e.g. 2-chloroethyl); and hydroxy C2 to C6 alkyl (e.g.
- Typical quaternary ammonium salts of formula (2) include the following: distearyl dimethyl ammonium chloride ditallow dimethyl ammonium chloride dihexadecyl dimethyl ammonium chloride distearyl dimethyl ammonium bromide di(hydrogenated tallow) dimethyl ammonium bromide distearyl, di(isopropyl) ammonium chloride distearyl dimethyl ammonium methosulfate. di (hydrogenated tallow) dimethyl ammonium methosulfate.
- Another preferred class of the cationic fabric softeners are diesterified long chain fatty acid dilower alkyl quaternary ammonium salts and diesterified long chain fatty acid lower alkyl lower hydroxy alkyl quaternary ammonium salts.
- This class of cationic fabric softeners can be represented by the general formula: wherein RCO represents the residue of a fatty acid having from about 12 to 24 carbon atoms; R2 and R3 represent independently a lower alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms, and preferably 1 to 3 carbon atoms; R4 represents a lower alkylene group having 1 to 4 carbon atoms, preferably 1 to 3, and most preferably has 2 carbon atoms, i.e.
- R4 is -- CH2CH2 --; and X is a water-solubilizing anion as defined above.
- Such compounds are commercially available from, for instance, Stepan Chemical Co. under the Stepantex trademark, such as Stepantex VHR90 which has the formula: where RCO is derived from tallow or coco fatty acids and X may be chloride or sulfate.
- the quaternary ammonium softening compound is generally from about 5 to 40%, by weight, of the particulate softening composition, preferably from about 10 to 30%, and most preferably from about 15 to 25%, by weight.
- An optional fabric softening ingredient is a fatty alcohol wherein the hydrophobic group may be a straight or branched chain alkyl or alkenyl group having from about 10 to 24, preferably from about 10 to 20, especially preferably from about 12 to 20 carbon atoms.
- the fatty alcohol include decanol, dodecanol, tetradecanol, pentadecanol, hexadecanol, octadecanol, lauryl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, and mixtures thereof.
- the fatty alcohol may be of natural or synthetic origin and may include, for example, mixed alcohol, such as C16 to C18 alcohols prepared by Ziegler polymerization of ethylene.
- the fatty alcohol may be present in the composition in a minor amount relative to the cationic fabric softener such that the ratio, by weight, of the cationic fabric softener to fatty alcohol is in the range of from about 6:1 to 2:1, especially preferably about 5:1 to 3:1.
- fatty acid alkanolamides useful in the present invention are those derived from fatty acid amides whose alkyl radical contains at least 12 carbon atoms. They preferably have the general formula: wherein n is 2 or 3. A preferred material is coco monoethanolamide.
- the concentration of fatty acid alkanolamide in the softening composition is generally from about 1 to 10%, by weight, and preferably from about 1 to 5%, by weight.
- the combination of fatty acid alkanolamide and quaternary ammonium softening compound in accordance with the invention provides a superior softening effect to fabrics.
- the particles generally contain from about 45 to 85%, by weight, of urea, preferably from about 55 to 75%, and most preferably from about 60 to 70%, by weight.
- anionic and/or nonionic surfactant Another important ingredient for purposes of improving particle solubility and dispersibility is an anionic and/or nonionic surfactant.
- anionic surface active agents useful in the present invention are those surface active compounds which contain an organic hydrophobic group containing from about 8 to 26 carbon atoms and preferably from about 10 to 18 carbon atoms in their molecular structure and at least one water-solubilizing group selected from the group of sulfonate, sulfate, carboxylate, phosphorate and phosphate so as to form a water-soluble detergent.
- Suitable anionic detergents include soaps, such as, the water-soluble salts (e.g., the sodium potassium, ammonium and alkanolammonium salts) of higher fatty acids or resin salts containing from about 8 to 20 carbon atoms and preferably 10 to 18 carbon atoms. Particularly useful are the sodium and potassium salts of the fatty acid mixtures derived from coconut oil and tallow, for example, sodium coconut soap and potassium tallow soap.
- the water-soluble salts e.g., the sodium potassium, ammonium and alkanolammonium salts
- the sodium and potassium salts of the fatty acid mixtures derived from coconut oil and tallow for example, sodium coconut soap and potassium tallow soap.
- the anionic class of detergents also includes the water-soluble sulfated and sulfonated detergents having an aliphatic, preferably an alkyl radical containing from about 8 to 26, and preferably from about 12 to 22 carbon atoms.
- the sulfonated anionic detergents are the higher alkyl aromatic sulfonates such as the higher alkyl benzene sulfonates containing from about 10 to 16 carbon atoms in the higher alkyl group in a straight or branched chain, such as, for example, the sodium, potassium and ammonium salts of higher alkyl benzene sulfonates, higher alkyl toluene sulfonates and higher alkyl phenol sulfonates.
- Suitable anionic detergents are the olefin sulfonates including long chain alkene sulfonates, long chain hydroxyalkane sulfonates or mixtures of alkene sulfonates and hydroxyalkane sulfonates and hydroxyalkane sulfonates.
- Suitable anionic detergents are sulfated ethoxylated higher fatty alcohols of the formula RO(C2H4O) m SO3M, wherein R is a fatty alkyl of from 10 to 18 carbon atoms, m is from 2 to 6 (preferably having a value from about 1/5 to 1/2 the number of carbon atoms in R) and M is a solubilizing salt-forming cation, such as an alkali metal, ammonium, lower alkylamino or lower alkanolamino, or a higher alkyl benzene sulfonate wherein the higher alkyl is of 10 to 15 carbon atoms.
- R is a fatty alkyl of from 10 to 18 carbon atoms
- m is from 2 to 6 (preferably having a value from about 1/5 to 1/2 the number of carbon atoms in R)
- M is a solubilizing salt-forming cation, such as an alkali metal, ammonium, lower alkylamino or
- the proportion of ethylene oxide in the polyethoxylated higher alkanol sulfate is preferably 2 to 5 moles of ethylene oxide groups per mole of anionic detergent, with three moles being most preferred, especially when the higher alkanol is of 11 to 15 carbon atoms.
- a preferred polyethoxylated alcohol sulfate detergent is marketed by Shell Chemical Company as Neodol 25-3S.
- the most highly preferred water-soluble anionic detergent compounds are the ammonium and substituted ammonium (such as mono, di and triethanolamine), alkali metal (such as, sodium and potassium) and alkaline earth metal (such as, calcium and magnesium) salts of the higher alkyl benzene sulfonates, olefine sulfonates and higher alkyl sulfates.
- alkali metal such as, sodium and potassium
- alkaline earth metal such as, calcium and magnesium
- the most preferred are the sodium linear alkyl benzene sulfonates (LABS), and especially those wherein the alkyl group is a straight chain alkyl radical of 12 or 13 carbon atoms.
- nonionic surfactants are the ethoxylated fatty alcohols having from 12 to 20 carbon atoms, and an average degrees of ethoxylation of 3 to 9.
- Preferred nonionic detergents are coconut alcohols having an average of 6 or 7 ethyoxy groups per molecule and C14-C15 primarily alcohols with 6 or 7 ethoxy groups per mole of higher fatty alcohol.
- Ethoxylated lauryl alcohol having about 7 moles of ethoxylate per mole of alcohol is particularly preferred for use herein.
- Nonionic detergent compounds include the alkylpolyglycoside and alkylpolysaccharide surfactants which are well known in the art.
- the amount of anionic surfactant in the particulate composition may vary from 0 to 8%, and preferably will vary with the percentage of cationic softening compound as follows: from about 1 to 4% of anionic surfactant when the percentage of cationic compound is below about 20%, and from about 3 to 8% of anionic surfactant when the percentage of cationic softening compound is from about 20 to 40%, all percentages being by weight of the particulate composition.
- the level of anionic surfactant is from about 2 to 4%, by weight.
- the nonionic surfactant is optionally present from about 0.5 to 5%, by weight, and preferably no more than about 1%, by weight.
- the fabric softening compositions of the invention may further include additional or supplemental ingredients which do not adversely affect the stability or functional characteristics of the softening composition. Included among such supplemental ingredients are perfumes, dyes, pigments, germicides, soil-release agents, fabric crisping agents, anti-oxidants and anti-corrosion agents.
- a granular fabric softening composition of the invention had the following composition: Component Weight Percent DSDMAC1 24 Nonionic Surfactant2 2 Sodium Dodecyl Benzene Sulfonate 3 Cocomonoethanol Amide 3 Urea 64 Moisture Balance 1Distearyl dimethyl ammonium chloride 2Ethoxylated lauryl alcohol having about 7 moles of ethoxylate per mole of alcohol.
- the softness and hydrophilicity of the resulting fabrics was measured and compared with the measured softness for fabrics conditioned in the same top loading machine with forty two (42) grams of a commercial liquid fabric softener containing 6% of a quaternary ammonium softener.
- the fabrics conditioned with the granular softening composition of the invention were measurably softer and equal in hydrophilic properties to those conditioned with the commercial liquid product.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US80966091A | 1991-12-18 | 1991-12-18 | |
US809660 | 1991-12-18 | ||
US838626 | 1992-02-19 | ||
US07/838,626 US5368755A (en) | 1991-12-18 | 1992-02-19 | Free-flowing powder fabric softening composition and process for the manufacture of a free-flowing fabric softening composition |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0547722A1 true EP0547722A1 (de) | 1993-06-23 |
Family
ID=27123244
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92203997A Withdrawn EP0547722A1 (de) | 1991-12-18 | 1992-12-17 | Freifliessendes wäscheweichmachendes Pulver und Verfahren zu seiner Herstellung |
Country Status (18)
Country | Link |
---|---|
EP (1) | EP0547722A1 (de) |
CN (1) | CN1075759A (de) |
AU (1) | AU662780B2 (de) |
BG (1) | BG61343B1 (de) |
BR (1) | BR9205056A (de) |
CA (1) | CA2085618A1 (de) |
CZ (1) | CZ367592A3 (de) |
FI (1) | FI925743A (de) |
GR (1) | GR920100560A (de) |
HU (2) | HU9203998D0 (de) |
MX (1) | MX9207416A (de) |
NO (1) | NO924891L (de) |
NZ (1) | NZ245495A (de) |
PL (1) | PL174970B1 (de) |
PT (1) | PT101133A (de) |
SG (1) | SG55087A1 (de) |
SK (1) | SK367592A3 (de) |
TR (1) | TR26894A (de) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994006899A1 (de) * | 1992-09-11 | 1994-03-31 | Henkel Kommanditgesellschaft Auf Aktien | Detergensgemische |
WO1995004810A1 (de) * | 1993-08-11 | 1995-02-16 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von wasserfreien stickstoffhaltigen verbindungen |
EP0714976A1 (de) * | 1994-12-02 | 1996-06-05 | The Procter & Gamble Company | Kationisches Tensid enthaltende Waschmittelzusammensetzungen sowie deren Herstellungsverfahren |
EP0881279A2 (de) † | 1997-05-26 | 1998-12-02 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung kationtensidhaltiger Granulate |
US6502325B1 (en) * | 1999-09-02 | 2003-01-07 | Colgate-Palmolive Co. | Method of treating fabric with fabric care composition containing polycarboxylate polymer and compound derived from urea |
WO2003083026A1 (en) * | 2002-03-28 | 2003-10-09 | Unilever Plc | Solid fabric conditioning compositions |
Citations (2)
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DE2454465A1 (de) * | 1974-11-16 | 1976-05-20 | Hoechst Ag | Pulverfoermige waescheweichspuelmittel mit desinfizierenden eigenschaften |
EP0018630A1 (de) * | 1979-05-07 | 1980-11-12 | Henkel Kommanditgesellschaft auf Aktien | Waschmittel für Textilien |
Family Cites Families (2)
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JPS60398B2 (ja) * | 1978-06-08 | 1985-01-08 | ライオン株式会社 | 洗剤スラリ−の製造法 |
US5259964A (en) * | 1991-12-18 | 1993-11-09 | Colgate-Palmolive Co. | Free-flowing powder fabric softening composition and process for its manufacture |
-
1992
- 1992-12-15 SK SK3675-92A patent/SK367592A3/sk unknown
- 1992-12-15 CZ CS923675A patent/CZ367592A3/cs unknown
- 1992-12-15 AU AU30177/92A patent/AU662780B2/en not_active Ceased
- 1992-12-16 PT PT101133A patent/PT101133A/pt not_active Application Discontinuation
- 1992-12-16 NZ NZ245495A patent/NZ245495A/en unknown
- 1992-12-17 HU HU9203998A patent/HU9203998D0/hu unknown
- 1992-12-17 TR TR01206/92A patent/TR26894A/xx unknown
- 1992-12-17 SG SG1996005421A patent/SG55087A1/en unknown
- 1992-12-17 FI FI925743A patent/FI925743A/fi not_active Application Discontinuation
- 1992-12-17 NO NO92924891A patent/NO924891L/no unknown
- 1992-12-17 HU HU9203998A patent/HUT63473A/hu unknown
- 1992-12-17 EP EP92203997A patent/EP0547722A1/de not_active Withdrawn
- 1992-12-17 CA CA002085618A patent/CA2085618A1/en not_active Abandoned
- 1992-12-17 BR BR9205056A patent/BR9205056A/pt not_active Application Discontinuation
- 1992-12-18 GR GR920100560A patent/GR920100560A/el unknown
- 1992-12-18 BG BG97197A patent/BG61343B1/bg unknown
- 1992-12-18 CN CN92114693A patent/CN1075759A/zh active Pending
- 1992-12-18 MX MX9207416A patent/MX9207416A/es not_active IP Right Cessation
- 1992-12-18 PL PL92297067A patent/PL174970B1/pl unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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DE2454465A1 (de) * | 1974-11-16 | 1976-05-20 | Hoechst Ag | Pulverfoermige waescheweichspuelmittel mit desinfizierenden eigenschaften |
EP0018630A1 (de) * | 1979-05-07 | 1980-11-12 | Henkel Kommanditgesellschaft auf Aktien | Waschmittel für Textilien |
Non-Patent Citations (2)
Title |
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PATENT ABSTRACTS OF JAPAN vol. 4, no. 22 (C-74)(1980) & JP-A-54 160 404 ( LION YUSHI K.K ) 19 December 1979 * |
SEIFEN-öLE-FETTE-WACHSE vol. 15, no. 111, 1985, pages 445 - 447 'spray-drying' * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994006899A1 (de) * | 1992-09-11 | 1994-03-31 | Henkel Kommanditgesellschaft Auf Aktien | Detergensgemische |
EP0838518A2 (de) * | 1992-09-11 | 1998-04-29 | Henkel Kommanditgesellschaft auf Aktien | Detergensgemische |
EP0838518A3 (de) * | 1992-09-11 | 1998-11-25 | Henkel Kommanditgesellschaft auf Aktien | Detergensgemische |
WO1995004810A1 (de) * | 1993-08-11 | 1995-02-16 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von wasserfreien stickstoffhaltigen verbindungen |
EP0714976A1 (de) * | 1994-12-02 | 1996-06-05 | The Procter & Gamble Company | Kationisches Tensid enthaltende Waschmittelzusammensetzungen sowie deren Herstellungsverfahren |
EP0881279A2 (de) † | 1997-05-26 | 1998-12-02 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung kationtensidhaltiger Granulate |
EP0881279B2 (de) † | 1997-05-26 | 2007-04-18 | Cognis IP Management GmbH | Kationtensidhaltige Granulate |
US6502325B1 (en) * | 1999-09-02 | 2003-01-07 | Colgate-Palmolive Co. | Method of treating fabric with fabric care composition containing polycarboxylate polymer and compound derived from urea |
WO2003083026A1 (en) * | 2002-03-28 | 2003-10-09 | Unilever Plc | Solid fabric conditioning compositions |
US6914042B2 (en) | 2002-03-28 | 2005-07-05 | Unilever Home & Personal Care Usa, A Division Of Conopco, Inc. | Solid fabric conditioning compositions |
Also Published As
Publication number | Publication date |
---|---|
CA2085618A1 (en) | 1993-06-19 |
PL297067A1 (en) | 1993-09-20 |
CN1075759A (zh) | 1993-09-01 |
HU9203998D0 (en) | 1993-03-29 |
CZ367592A3 (en) | 1993-09-15 |
GR920100560A (el) | 1993-08-31 |
BG97197A (bg) | 1993-12-24 |
TR26894A (tr) | 1994-08-22 |
AU3017792A (en) | 1993-07-01 |
HUT63473A (en) | 1993-08-30 |
FI925743A (fi) | 1993-06-19 |
BR9205056A (pt) | 1993-06-22 |
FI925743A0 (fi) | 1992-12-17 |
NO924891D0 (no) | 1992-12-17 |
SG55087A1 (en) | 1998-12-21 |
PT101133A (pt) | 1994-03-31 |
SK367592A3 (en) | 1995-02-08 |
PL174970B1 (pl) | 1998-10-30 |
NO924891L (no) | 1993-06-21 |
AU662780B2 (en) | 1995-09-14 |
NZ245495A (en) | 1994-09-27 |
BG61343B1 (bg) | 1997-06-30 |
MX9207416A (es) | 1993-06-01 |
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