WO2010033897A1 - Cleaning composition containing substituted starch - Google Patents
Cleaning composition containing substituted starch Download PDFInfo
- Publication number
- WO2010033897A1 WO2010033897A1 PCT/US2009/057651 US2009057651W WO2010033897A1 WO 2010033897 A1 WO2010033897 A1 WO 2010033897A1 US 2009057651 W US2009057651 W US 2009057651W WO 2010033897 A1 WO2010033897 A1 WO 2010033897A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- range
- degree
- substitution
- substituent
- cleaning composition
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 80
- 229920002472 Starch Polymers 0.000 title claims abstract description 62
- 238000004140 cleaning Methods 0.000 title claims abstract description 62
- 235000019698 starch Nutrition 0.000 title claims abstract description 62
- 239000008107 starch Substances 0.000 title claims abstract description 61
- 238000006467 substitution reaction Methods 0.000 claims abstract description 45
- 239000004094 surface-active agent Substances 0.000 claims abstract description 32
- 125000001424 substituent group Chemical group 0.000 claims abstract description 24
- 229920000642 polymer Polymers 0.000 claims description 18
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- 239000003599 detergent Substances 0.000 claims description 6
- 239000004744 fabric Substances 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 5
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 2
- 230000003796 beauty Effects 0.000 claims 1
- 238000004851 dishwashing Methods 0.000 claims 1
- 239000002453 shampoo Substances 0.000 claims 1
- 239000000344 soap Substances 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- -1 alkylbenzene sulfonate Chemical class 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 17
- 239000000178 monomer Substances 0.000 description 16
- 239000003945 anionic surfactant Substances 0.000 description 9
- 125000002091 cationic group Chemical group 0.000 description 9
- 239000011734 sodium Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Chemical group 0.000 description 4
- 150000001340 alkali metals Chemical group 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 150000003839 salts Chemical group 0.000 description 4
- 229940071089 sarcosinate Drugs 0.000 description 4
- 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 3
- 150000008051 alkyl sulfates Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- CIOXZGOUEYHNBF-UHFFFAOYSA-N (carboxymethoxy)succinic acid Chemical compound OC(=O)COC(C(O)=O)CC(O)=O CIOXZGOUEYHNBF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229960004585 etidronic acid Drugs 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920005646 polycarboxylate Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- VJSWLXWONORKLD-UHFFFAOYSA-N 2,4,6-trihydroxybenzene-1,3,5-trisulfonic acid Chemical compound OC1=C(S(O)(=O)=O)C(O)=C(S(O)(=O)=O)C(O)=C1S(O)(=O)=O VJSWLXWONORKLD-UHFFFAOYSA-N 0.000 description 1
- CFPOJWPDQWJEMO-UHFFFAOYSA-N 2-(1,2-dicarboxyethoxy)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)OC(C(O)=O)CC(O)=O CFPOJWPDQWJEMO-UHFFFAOYSA-N 0.000 description 1
- NGOZDSMNMIRDFP-UHFFFAOYSA-N 2-[methyl(tetradecanoyl)amino]acetic acid Chemical compound CCCCCCCCCCCCCC(=O)N(C)CC(O)=O NGOZDSMNMIRDFP-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
- 229920000945 Amylopectin Polymers 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 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
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 239000007844 bleaching agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000000551 dentifrice Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 1
- 229940071106 ethylenediaminetetraacetate Drugs 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 229940071145 lauroyl sarcosinate Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940070782 myristoyl sarcosinate Drugs 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 229940096978 oral tablet Drugs 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-K pentetate(3-) Chemical compound OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O QPCDCPDFJACHGM-UHFFFAOYSA-K 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical group [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
- C11D3/228—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin with phosphorus- or sulfur-containing groups
-
- 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
- C11D3/0026—Low foaming or foam regulating 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0094—High foaming compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
- C11D3/225—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin etherified, e.g. CMC
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
- C11D3/227—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin with nitrogen-containing groups
-
- 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
- C11D3/3796—Amphoteric polymers or zwitterionic polymers
-
- 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 cleaning composition
- a cleaning composition comprising starch substituted with anionic and/or nonionic substituent. More particularly, the substituted starch in the present invention provide suds boosting benefit, such as suds volume and suds duration enhancement, to cleaning compositions such as fabric care products, dish care products, oral care product, or applications where cleaning of surfaces is needed.
- Cleaning compositions must satisfy several criteria in order to be effective and fulfill the need of the consumer.
- the presence of suds in a cleaning operation has long been used as a signal that the detergent continues to be effective.
- the presence of suds or the lack thereof may have little or no bearing upon the efficacy of the cleaning process. Therefore, the consumer who relies upon a somewhat erroneous signal may tend to use an excess of cleaning product in the lack or absence of suds.
- the present disclosure relates to a cleaning composition
- a cleaning composition comprising from 0.05% to 30% by weight of surfactant and from 0.01% to 10% by weight of substituted starch polymer, wherein the substituted starch has: a total degree of substitution in the range of from 0.001 and 0.6, a degree of substitution of anionic substituent in the range of from 0.001 to 0.04 and/or a degree of substation of nonionic substituent in the range of from 0.01 to 0.5, a degree of substitution of cationic substituent in the range of from 0 to 0.004, an average per weight molecular weight in the range of from 10 000 to 100 000 000 000
- the invention concerns the use of a substituted starch, wherein the substituted starch has: a total degree of substitution in the range of from 0.001 and 0.6, a degree of substitution of anionic substituent in the range of from 0.001 and 0.04 and/or a degree of substation of nonionic substituent in the range of from 0.01 and 0.5, a degree of substitution of cationic substituent in the range of from 0 to 0.004, an average per weight molecular weight in the range of from 10 000 to 100 000 000 Daltons, to increase the quantity of suds that can be generated by a cleaning composition.
- the cleaning composition of the invention comprises from 0.01% to 10% by weight of one or more substituted starch.
- the cleaning composition of the invention comprises from 0.1% to 7% by weight of substituted starch, in particular from 0.1% to 5%, typically from 0.3% to 3% by weight of substituted starch polymer.
- the starch polymer comprises sugar monomers.
- the sugar monomers can be substituted or not substituted. When the sugar monomer is substituted, one or more of its hydroxy function may be substituted.
- the substituted starch of the invention has a total degree of substitution (DSt) in the range of from 0.001 to 0.6.
- the substituted starch has a DSt of in the range of from 0.003 to 0.3, in particular in the range of from 0.01 to 0.2.
- DSt corresponds to the ratio between the sugar monomers which are substituted to the total number of sugar monomers of the starch polymer. If all the sugar monomers are substituted at least once, the value of DSt is 1.
- the substituted starch of the invention has a DSt in the range of from 0.001 and 0.6, typically between 0.01 and 0.5.
- degree of substitution of a specific substituent refers to the ratio of sugar momomers which are substituted at least once with said specific substituent to the total number of sugar monomers of the starch polymer.
- DSa corresponds to the ratio between the sugar monomers of the starch polymer which are substituted with at least one anionic substituent and the total number of sugar monomers of the starch polymer. If all the sugar monomers are substituted with at least one anionic substituent, the value of DSa is 1.
- DSn corresponds to the ratio between the sugar monomers of the starch polymer which are substituted with at least one nonionic substituent and the total number of sugar monomers of the starch polymer. If all the sugar monomers are substituted with at least one nonionic substituent, the value of DSn is 1.
- DSc corresponds to the ratio between the sugar monomers of the starch polymer which are substituted with at least one cationic substituent and the total number of sugar monomers of the starch polymer. If all the sugar monomers are substituted with at least one cationic substituent, the value of DSc is 1.
- a substituent is considered anionic, cationic or nonionic, depending of its net charge value at a pH of 10.
- the substituted starch of the invention has a degree of substitution of anionic substituent (DSa) in the range of from 0.001 to 0.04 and/or a degree of substitution of nonionic substituent (DSn) in the range of from 0.01 to 0.5.
- the substituted starch of the invention may have a degree of substitution of anionic substituent in the range of from 0.001 to 0.04, preferably in the range of from 0.003 to 0.02, in particular in the range of from 0.01 to 0.01.
- the substituted starch of the invention may have a degree of substation of nonionic substituent in the range of from 0.01 and 0.5, preferably in the range of from 0.03 to 0.3, in particular in the range of from 0.08 to 0.15.
- the substituted starch of the invention has a degree of substitution of cationic substituent DSc in the range of from 0 to 0.004.
- the substituted starch has a DSc in the range of from 0 to 0.02, typically in the range of from 0 to 0.001 or from 0 to 0.0005 or from 0 to 0.0002 or even from 0 to 0.0001 or from 0 to 0.00002.
- the DSc is below the DSa.
- the substituted starch has preferably an overall net negative charge.
- the ratio DSc to DSa, per number of substituent is below 1, typically below 0.9 or 0.75 or 0.5, or even below 0.3 or 0.1 or 0.05 or 0.01 or 0.001.
- substituted starch comprising a low DSc, in particular having a DSc below the DSa, were particularly suitable for providing the sudsing benefit of the invention.
- the substituted starch of the invention has an average per weight molecular weight in the range of from 10 000 to 100 000 000 Daltons. Preferably the substituted starch has an average per weight molecular weight of from 20 000 to 50 000 000 Daltons.
- the substituted starch has a DSa above 0.001, for example above 0.005 or 0.01, the substituted starch has an average per weight molecular weight in the range of from 20 000 to 500 000. Daltons, preferably in the range of from 40 000 to 200 000 or from 70 000 to 150 000.
- the substituted starch has a DSa above 0.01, and a DSc above 0.01.
- the substituted starch has an average per weight molecular weight in the range of from 100 000 to 100 000 000 Daltons, preferably in the range of from 200 000 to 50 000 000 or from 500 000 to 10 000 000 or even from 1 000 000 to 5 000 000.
- the substituted starch may have a degree of substitution of nonionic hydroxyalkyl substituent in the range of from 0.01 and 0.5.
- the substituted starch has a degree of substitution of nonionic hydroxyalkyl substituent in the range of from 0.03 to 0.3, or from 0.08 to 0.15.
- the substituted starch may have a degree of substitution of anionic substituent comprising a sulphate or sulphonate group in the range of from 0.001 and 0.4, preferably in the range of from 0.003 to 0.1, in particular in the range of from 0.005 to 0.2.
- starches substituted with anionic substituent comprising a sulphate or sulphonate group or with nonionic hydroxyalkyl substituent were particularly suitable to provide the sudsing benefit of the invention.
- Starch comprises amylose (see formula I below) and amylopectin (see formula II below). Starch is described in Kirk-Othmer's Encyclopedia of Chemical Technology 4 th Edition, Vol. 22, at pp. 699-719.
- the substituted starch may comprise substituted polymers selected from polymers of general formula:
- each R is H or a substituent selected from the group of anionic substituent, nonionic substituent, and cationic substituent, wherein at least 70% by number of the R are H, the degree of substitution of anionic substituent is in the range of from 0 to 0.04, the degree of substitution of nonionic substituent is in the range of from 0 to 0.5, the degree of substitution of cationic substituent is in the range of from 0 to 0.004, wherein either the degree of substitution of anionic substituent is of at least 0.002 or the degree of substitution of nonionic is of at least 0.02, wherein n is such that said suds boosting substituted polymer(s) has an average per weight molecular weight ranging from 20 000 Daltons to 100 000 000 Daltons.
- Suitable anionic, nonionic, or cationic substituents may be selected from the group consisting of branched, linear or cyclic, substituted or not substituted, saturated or unsaturated alkyl, amine (primary, secondary, tertiary), ammonium salt, amide, urethane, alcohol, carboxylic acid, tosylate, sulfonate, sulfate, nitrate, phosphate, silicone, and mixtures thereof.
- the anionic, nonionic, and cationic substituents may be selected from the group consisting of: R 1 , N(R 2 )(Rs), silicone moiety, S(V, P(V, with R 2 and R 3 being independently of each other an hydrogen atom or a Ci_ 6 alkyl and Ri being a linear or branched, typically linear, saturated or unsaturated, typically saturated, substituted or unsubstituted, typically substituted, cyclic or acyclic, typically acyclic, aliphatic or aromatic, typically aliphatic, Ci- C300, typically C 1 -C30, Ci-Ci 2 , or Ci-C 6 hydrocarbon radical which hydrocarbon backbone may be interrupted by a heteroatom chosen form O, S, N and P.
- Ri may be substituted by one or more radical selected from amino (primary, secondary, or tertiary), amido, -OH, -CO-OR 4 , -SO 3 " , R 4 , -CN, and -CO-R 4 , where R 4 represents a hydrogen atom or an alkali metal, preferably a sodium or potassium, ion.
- the anionic substituent may be one following anionic groups, in its acid or salt form, preferably sodium (given here) or potassium salt form:
- T is a Cl-6 alkyl, more preferably Cl-4 alkyl.
- the cationic substituent may be the following cationic group:
- T is a Ci_ 6 alkyl, or CH 2 CH(OH)CH 2
- each A, B, and C is Ci -6 alkyl or hydroxy-Ci_6 alkyl
- X is a counterion i such as halide or tosylate.
- the nonionic substituent may be one following non- ionic groups:
- the anionic substituent comprises a sulphate or sulphonate group.
- the nonionic substituent is a nonionic hydroxyalkyl wherein the alkyl is a Ci-C 6 alkyl, in particular a Ci-C 4 or C 1 -C3 or Ci-C 2 alkyl.
- the ratio of the degree of substitution of anionic substituent comprising a sulphate or sulphonate group to the total degree of substitution of anionic substituent is in the range of from 1:5 to 1:1, preferably above 1:3 or 1:2 or even 1:1.5 or 1:1.2 or 1:1.1.
- the ratio of the degree of substitution of nonionic hydroxyalkyl substituent wherein the alkyl is a Ci-C 6 alkyl, to the total degree of substitution of nonionic substituent is in the range of from 1:5 to 1:1, preferably above 1:3 or 1:2 or even 1:1.5 or 1:1.2 or 1: 1.1.
- the cleaning composition of the invention comprises from 0.05% to 30% by weight of one or more surfactant(s).
- the cleaning composition comprises from 0.1% to 25% of surfactant, typically from 0.5% to 20%, or from 1% to 15% by weight of surfactant.
- the surfactant may be anionic, nonionic and/or cationic.
- the substituted starch of the invention is particularly efficient in the presence of anionic surfactant.
- the weight ratio of substituted starch to surfactant may be in the range of from 1:100 to 1:3, in particular from 1:50 to 1:5, or from 1:40 to 1:10, or from 1:30 to 1:20.
- the weight ratio of substituted starch to anionic surfactant may be in the range of from 1:100 to 1:3, in particular from 1:50 to 1:5, or from 1:40 to 1:10, or from 1:30 to 1:20.
- the weight ratio of nonionic surfactant to anionic surfactant may be in the range of from 1:100 to 1:1, in particular from 1:50 to 1:5, for example below 1:10 or 1:20.
- the cleaning composition of the invention may comprise from 0.05% to 30% by weight of one or more anionic surfactant.
- the cleaning composition may comprise 0.1% to 25%, in particular from 0.5 % to 20% or from 1% to 18%, or even from 1.5% to 16% or from 2% to 14% by weight of anionic surfactant.
- the anionic surfactant may comprise anionic surfactants selected from alkyl ester sulfonate(s); linear, branched, and modified alkylbenzene sulfonate(s); Ci O -Ci 8 alkyl alkoxy sulfates; Cio- 2 0 primary, branched-chain and random alkyl sulfates; CiO-Ci 8 secondary (2,3) alkyl sulfates; Ci O -Ci 8 alkyl alkoxy carboxylate(s); fatty acid(s); mid-chain branched alkyl sulfate(s); mid-chain branched alkyl alkoxy sulfate(s); alpha-olefin sulfonate(s); phosphate ester(s); and mixtures thereof.
- anionic surfactants selected from alkyl ester sulfonate(s); linear, branched, and modified alkylbenzene sulfonate(s); Ci O
- the anionic surfactant may comprise surfactant chosen among sarcosinate surfactants, isethionate surfactants and taurate surfactants.
- Preferred for use herein are alkali metal or ammonium salts of these surfactants.
- Most preferred herein are the sodium and potassium salts of the following: lauroyl sarcosinate, myristoyl sarcosinate, palmitoyl sarcosinate, stearoyl sarcosinate and oleoyl sarcosinate.
- the cleaning composition may comprise non-ionic surfactant.
- the non- ionic detersive surfactant(s) is generally present in amounts of from 0.01wt% to 20wt%, or from 0.1 wt% to 4wt% by weight of the cleaning composition.
- the cleaning composition may comprise a cationic detersive surfactant.
- the cleaning composition comprises from 0.01wt% to 10 wt%, or from 0.1 wt% to 2wt% cationic detersive surfactant.
- Suitable cationic detersive surfactants are alkyl pyridinium compounds, alkyl quaternary ammonium compounds, alkyl quaternary phosphonium compounds, and alkyl ternary sulphonium compounds.
- the cationic detersive surfactant can be selected from the group consisting of: alkoxylate quaternary ammonium (AQA) surfactants as described in more detail in US 6,136,769; dimethyl hydroxyethyl quaternary ammonium surfactants as described in more detail in US 6,004,922; polyamine cationic surfactants as described in more detail in WO 98/35002, WO 98/35003, WO 98/35004, WO 98/35005, and WO 98/35006; cationic ester surfactants as described in more detail in US 4,228,042, US 4,239,660, US 4,260,529 and US 6,022,844; amino surfactants as described in more detail in US 6,221,825
- cationic detersive surfactants may be chosen among mono-Cg-io alkyl mono-hydroxyethyl di-methyl quaternary ammonium chloride, mono-Cio- 12 alkyl mono-hydroxyethyl di-methyl quaternary ammonium chloride and mono-Cio alkyl mono-hydroxyethyl di-methyl quaternary ammonium chloride.
- Cationic surfactants such as Praepagen HY (tradename Clariant) may be useful and may also be useful as a suds booster.
- the cleaning composition of the invention may comprise a builder.
- the cleaning composition will typically comprise from 1% to about 40%, typically from 2 to 20%, or even from about 4% to about 15%, or from 5 to 10% by weight of builder(s).
- composition may further comprise from 1% to about 40%, typically from 2 to 20%, or even from about 4% to about 15%, or from 5 to 10% by weight of builder(s), chelant(s), or, in general, any material which will remove calcium ions from solution by, for example, sequestration, complexation, precipitation or ion exchange.
- the composition may comprise a chelant.
- Suitable chelants include diethylene triamine pentaacetate, diethylene triamine penta(methyl phosphonic acid), ethylene diamine-N'N'- disuccinic acid, ethylene diamine tetraacetate, ethylene diamine tetra(methylene phosphonic acid) and hydroxy ethane di(methylene phosphonic acid).
- a preferred chelant is ethylene diamine-N'N'-disuccinic acid (EDDS) and/or hydroxyethane diphosphonic acid (HEDP).
- EDDS ethylene diamine-N'N'-disuccinic acid
- HEDP hydroxyethane diphosphonic acid
- the ethylene diamine-N'N'-disuccinic acid is in S'S' enantiomeric form.
- the composition of the invention may comprise less than 3% or less than 2% or l%or 0.5% of each of the above mentioned chelants.
- Builders include, but are not limited to, the alkali metal, ammonium and alkanolammonium salts of polyphosphates, alkali metal silicates, layered silicates, such as SKS-6 of Clariant ® , alkaline earth and alkali metal carbonates, aluminosilicate builders, such as zeolite, and polycarboxylate compounds, ether hydroxypolycarboxylates, copolymers of maleic anhydride with ethylene or vinyl methyl ether, 1, 3, 5-trihydroxy benzene-2, 4, 6-trisulphonic acid, and carboxymethyloxysuccinic acid, fatty acids, the various alkali metal, ammonium and substituted ammonium salts of polyacetic acids such as ethylenediamine tetraacetic acid and nitrilotriacetic acid, as well as polycarboxylates such as mellitic acid, succinic acid, citric acid, oxydisuccinic acid, polymaleic acid,
- the cleaning composition may comprise less than 50%, in particular less than 25% or less than 20%, 15%, 10%, or 5% by weight of phosphate and/or aluminosilicate builders.
- the cleaning composition may comprise from 0 to 50%, in particular from 1% to 25%, or less than 20%, or less than 15%, or less than 10%, or less than 5%, or less than 1% by weight of phosphate builder(s).
- the cleaning composition may comprise from 0 to 50%, in particular from 1% to 25%, or less than 20%, or less than 15%, or less than 10%, or less than 5%, or less than 1% by weight of aluminosilicate builder(s).
- the aluminosilicate builder may comprise zeolite.
- the cleaning composition may comprise from 0 to 50%, in particular from 1% to 25%, or less than 20%, or less than 15%, or less than 10%, or less than 5%, or less than 1% by weight of of polycarboxylic acid(s) and salt(s) thereof.
- the cleaning composition may comprise from 0 to 50%, in particular from 1% to 25%, or less than 20%, or less than 15%, or less than 10%, or less than 5%, or less than 1% by weight of layered silicate(s).
- the cleaning compositions of the present invention may comprise from 0 to 50%, in particular from 1% to 25%, or less than 20%, or less than 15%, or less than 10%, or less than 5%, or less than 1% by weight of sodium carbonate.
- the cleaning composition may comprise one or more adjunct ingredient(s).
- additional adjunct components and levels of incorporation thereof, will depend on the physical form of the composition and the nature of the operation for which it is to be used.
- suitable adjunct materials include, but are not limited to flocculating aid, chelating agents, dye transfer inhibitors, enzymes, enzyme stabilizers, catalytic materials, bleach activators, hydrogen peroxide, sources of hydrogen peroxide, preformed peracids, polymeric dispersing agents, clay soil removal/anti- redeposition agents, brighteners, suds suppressors, dyes, perfumes, structure elasticizing agents, fabric softeners, carriers, hydrotropes, processing aids, and/or pigments.
- suitable examples of such other adjuncts and levels of use are found in U.S. Patent Nos. 5,576,282, 6,306,812 Bl and 6,326,348 Bl.
- the cleaning composition may also comprise, in particular when the cleaning composition is an oral care composition, Antic alculus Agent, Fluoride Source, Thickening Agents, Flavoring and Sweetening Agents, and/or antimicrobial agents.
- the cleaning composition of the invention contains less than 3%, preferably up to 1%, and most preferably less than 0.1% or less than 0.01% or 0.001% or even 0.0001% of suds suppressor selected from the group consisting of trimethyl-, diethyl-, dipropyl-, dibutyl-, methylethyl-, phenylmethyl polysiloxane, and mixtures thereof.
- the compositions of the invention contain less than 3%, preferably up to 1%, and most preferably less than 0.1% or less than 0.01% or 0.001% or even 0.0001% of suds suppressor.
- the cleaning composition may be in any liquid or solid form, in the form of gel, paste, dispersion, preferably a colloidal dispersion or any combination thereof.
- the cleaning composition is preferably in a solid form or in the form of a paste.
- the cleaning composition may be in particulate form, for example in free-flowing particulate form.
- the composition in solid form can be in the form of an agglomerate, granule, flake, extrudate, bar, tablet or any combination thereof.
- the cleaning composition may be capable of cleaning and/or softening fabric during a laundering process.
- the cleaning composition may be an oral care composition.
- the Oral care composition may be in the form of a toothpaste, dentifrice, tooth powder, tooth gel, subgingival gel, mouthrinse, denture product, mouthspray, lozenge, oral tablet, or chewing gum.
- the oral composition may also be incorporated onto strips or films for direct application or attachment to oral surfaces.
- the cleaning composition may be a hair care, or a dish care composition.
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Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09792764A EP2324105A1 (en) | 2008-09-19 | 2009-09-21 | Cleaning composition containing substituted starch |
BRPI0918812A BRPI0918812A2 (en) | 2008-09-19 | 2009-09-21 | cleaning composition containing substituted starch. |
CN2009801373995A CN102159695A (en) | 2008-09-19 | 2009-09-21 | Cleaning composition containing substituted starch |
CA2736893A CA2736893A1 (en) | 2008-09-19 | 2009-09-21 | Cleaning composition containing substituted starch |
MX2011003035A MX2011003035A (en) | 2008-09-19 | 2009-09-21 | Cleaning composition containing substituted starch. |
ZA2011/01959A ZA201101959B (en) | 2008-09-19 | 2011-03-15 | Cleaning composition containing substituted starch |
US13/049,253 US20110229420A1 (en) | 2008-09-19 | 2011-03-16 | Cleaning Composition Containing Substituted Starch |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US9830808P | 2008-09-19 | 2008-09-19 | |
US61/098,308 | 2008-09-19 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US13/049,253 Continuation US20110229420A1 (en) | 2008-09-19 | 2011-03-16 | Cleaning Composition Containing Substituted Starch |
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WO2010033897A1 true WO2010033897A1 (en) | 2010-03-25 |
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Family Applications (2)
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PCT/US2009/057379 WO2010033746A1 (en) | 2008-09-19 | 2009-09-18 | Detergent composition containing suds boosting and suds stabilizing modified biopolymer |
PCT/US2009/057651 WO2010033897A1 (en) | 2008-09-19 | 2009-09-21 | Cleaning composition containing substituted starch |
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PCT/US2009/057379 WO2010033746A1 (en) | 2008-09-19 | 2009-09-18 | Detergent composition containing suds boosting and suds stabilizing modified biopolymer |
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US (2) | US8383572B2 (en) |
EP (2) | EP2324106A1 (en) |
JP (1) | JP2012503082A (en) |
CN (2) | CN102159696B (en) |
BR (2) | BRPI0918871A2 (en) |
CA (2) | CA2732925A1 (en) |
MX (2) | MX2011003034A (en) |
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Also Published As
Publication number | Publication date |
---|---|
US20100075879A1 (en) | 2010-03-25 |
BRPI0918871A2 (en) | 2019-09-24 |
CN102159696A (en) | 2011-08-17 |
US20110229420A1 (en) | 2011-09-22 |
CN102159695A (en) | 2011-08-17 |
MX2011003035A (en) | 2011-04-12 |
CA2732925A1 (en) | 2010-03-25 |
WO2010033746A1 (en) | 2010-03-25 |
MX2011003034A (en) | 2011-04-12 |
BRPI0918812A2 (en) | 2015-12-01 |
CA2736893A1 (en) | 2010-03-25 |
EP2324105A1 (en) | 2011-05-25 |
JP2012503082A (en) | 2012-02-02 |
ZA201101922B (en) | 2012-08-29 |
ZA201101959B (en) | 2012-08-29 |
EP2324106A1 (en) | 2011-05-25 |
US8383572B2 (en) | 2013-02-26 |
CN102159696B (en) | 2013-08-28 |
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