WO2020030760A1 - Détergent - Google Patents
Détergent Download PDFInfo
- Publication number
- WO2020030760A1 WO2020030760A1 PCT/EP2019/071369 EP2019071369W WO2020030760A1 WO 2020030760 A1 WO2020030760 A1 WO 2020030760A1 EP 2019071369 W EP2019071369 W EP 2019071369W WO 2020030760 A1 WO2020030760 A1 WO 2020030760A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyethyleneimine
- composition
- epei
- composition according
- starting material
- Prior art date
Links
- 239000003599 detergent Substances 0.000 title claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 127
- 229920002873 Polyethylenimine Polymers 0.000 claims abstract description 89
- -1 polyethylene Polymers 0.000 claims abstract description 61
- 239000007858 starting material Substances 0.000 claims abstract description 38
- 238000007046 ethoxylation reaction Methods 0.000 claims abstract description 37
- 239000007788 liquid Substances 0.000 claims abstract description 26
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 17
- 239000004094 surface-active agent Substances 0.000 claims abstract description 13
- 239000003945 anionic surfactant Substances 0.000 claims abstract description 11
- 238000004140 cleaning Methods 0.000 claims abstract description 11
- 239000000344 soap Substances 0.000 claims abstract description 11
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 25
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 14
- 239000004744 fabric Substances 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 12
- 229920001634 Copolyester Polymers 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 5
- 150000002009 diols Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004900 laundering Methods 0.000 claims description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 abstract description 2
- 229920000573 polyethylene Polymers 0.000 abstract description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
- 239000000463 material Substances 0.000 description 27
- 125000000217 alkyl group Chemical group 0.000 description 22
- 238000009472 formulation Methods 0.000 description 21
- 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 20
- 229910052708 sodium Inorganic materials 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 16
- 239000011734 sodium Substances 0.000 description 15
- 239000000178 monomer Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000004615 ingredient Substances 0.000 description 11
- 235000011118 potassium hydroxide Nutrition 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
- 229910052700 potassium Inorganic materials 0.000 description 10
- 239000011591 potassium Substances 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- 150000003141 primary amines Chemical group 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 6
- 150000003335 secondary amines Chemical group 0.000 description 6
- 150000003512 tertiary amines Chemical group 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000002738 chelating agent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000008051 alkyl sulfates Chemical class 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910001428 transition metal ion Inorganic materials 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 238000012644 addition polymerization Methods 0.000 description 3
- 239000003093 cationic surfactant Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical group [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 229920005646 polycarboxylate Polymers 0.000 description 3
- 159000000001 potassium salts Chemical class 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- YDONNITUKPKTIG-UHFFFAOYSA-N [Nitrilotris(methylene)]trisphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O YDONNITUKPKTIG-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 239000008365 aqueous carrier Substances 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000004064 cosurfactant Substances 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- 239000006254 rheological additive Substances 0.000 description 2
- 238000000518 rheometry Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000015424 sodium Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000004834 15N NMR spectroscopy Methods 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 1
- SFHBJXIEBWOOFA-UHFFFAOYSA-N 5-methyl-3,6-dioxabicyclo[6.2.2]dodeca-1(10),8,11-triene-2,7-dione Chemical compound O=C1OC(C)COC(=O)C2=CC=C1C=C2 SFHBJXIEBWOOFA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- 239000004382 Amylase Substances 0.000 description 1
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- 102100032487 Beta-mannosidase Human genes 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
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- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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- CMFFZBGFNICZIS-UHFFFAOYSA-N butanedioic acid;2,3-dihydroxybutanedioic acid Chemical class OC(=O)CCC(O)=O.OC(=O)CCC(O)=O.OC(=O)C(O)C(O)C(O)=O CMFFZBGFNICZIS-UHFFFAOYSA-N 0.000 description 1
- HXDRSFFFXJISME-UHFFFAOYSA-N butanedioic acid;2,3-dihydroxybutanedioic acid Chemical class OC(=O)CCC(O)=O.OC(=O)C(O)C(O)C(O)=O HXDRSFFFXJISME-UHFFFAOYSA-N 0.000 description 1
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- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
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- 125000001165 hydrophobic group Chemical group 0.000 description 1
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- 229920013821 hydroxy alkyl cellulose Polymers 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 229920001427 mPEG Polymers 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 238000000569 multi-angle light scattering Methods 0.000 description 1
- 239000007777 multifunctional material Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000004028 organic sulfates Chemical class 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 108010087558 pectate lyase Proteins 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical class [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- AVTYONGGKAJVTE-UHFFFAOYSA-L potassium tartrate Chemical class [K+].[K+].[O-]C(=O)C(O)C(O)C([O-])=O AVTYONGGKAJVTE-UHFFFAOYSA-L 0.000 description 1
- 239000001472 potassium tartrate Substances 0.000 description 1
- 235000011005 potassium tartrates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CUNPJFGIODEJLQ-UHFFFAOYSA-M potassium;2,2,2-trifluoroacetate Chemical compound [K+].[O-]C(=O)C(F)(F)F CUNPJFGIODEJLQ-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 235000019423 pullulan Nutrition 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910000031 sodium sesquicarbonate Inorganic materials 0.000 description 1
- 235000018341 sodium sesquicarbonate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- JZBRFIUYUGTUGG-UHFFFAOYSA-J tetrapotassium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical class [K+].[K+].[K+].[K+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O JZBRFIUYUGTUGG-UHFFFAOYSA-J 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- JEVFKQIDHQGBFB-UHFFFAOYSA-K tripotassium;2-[bis(carboxylatomethyl)amino]acetate Chemical class [K+].[K+].[K+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O JEVFKQIDHQGBFB-UHFFFAOYSA-K 0.000 description 1
- WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 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
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3723—Polyamines or polyalkyleneimines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic 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
-
- 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
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap 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
- 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 liquid laundry detergents comprising ethoxylated polyethyleneimine (EPEI) for an improved product viscosity profile without impairing cleaning performance.
- EPEI ethoxylated polyethyleneimine
- EPEI ethoxylated polyethyleneimine
- the present invention addresses this problem.
- the present invention provides a liquid laundry detergent composition comprising ethoxylated polyethyleneimine (EPEI) for an improved product viscosity profile without impairing cleaning performance; the detergent composition comprising: a) from 6 to 50% (by weight based on the total weight of the composition) of one or more detersive surfactants selected from non-soap anionic surfactants, nonionic surfactants and mixtures thereof, and
- EPEI ethoxylated polyethyleneimine
- EPEI ethoxylated polyethyleneimine
- polyethyleneimine backbone made up of repeating -[(CH CH )N]- subunits; and one or more polyoxyethylene side chains which are bonded to internal and/or terminal nitrogen atoms in the polyethyleneimine backbone;
- polyethyleneimine backbone is derived from a polyethyleneimine starting material which is ethoxylated to produce EPEI;
- the polyethyleneimine starting material has an average molecular weight (M w ) ranging from 1800 to 5000 g/mol (prior to ethoxylation), and the polyoxyethylene side chains have an average of from 25 to 40 ethoxy units per side chain bonded to the polyethyleneimine backbone.
- M w average molecular weight
- EPEI Ethoxylated polyethyleneimine
- the ethoxylated polyethyleneimine (EPEI) for use in the invention includes inter alia a polyethyleneimine backbone made up of repeating -[(CH CH )N]- subunits.
- the backbone derives from a polyethyleneimine starting material (as defined above) which is ethoxylated to produce EPEI.
- the polyethyleneimine starting material (prior to ethoxylation) has an average molecular weight (M w ) ranging from 1800 to 2400 g/mol, and most preferably from 1800 to 2200 g/mol, such as from 1900 to 2100 g/mol, determined by gel permeation chromatography (GPC) with 1.5% by weight aqueous formic acid as eluent and cross-linked poly-hydroxyethyl methacrylate as stationary phase (TSKgel GMPWXL column) and by using an Rl detector and Pullulan standards (PSS GmbH, Mainz, Germany) for calibration.
- M w average molecular weight
- a suitable polyethyleneimine starting material in the context of this invention may, for example, be a homopolymer of ethyleneimine conforming to the (empirical) formula -(CH 2 -CH 2 -NH) n - ; in which n ranges from about 40 to about 120. Preferably n ranges from about 40 to about 60.
- the polyethyleneimine starting material can vary in shape, including for example linear, branched, dendritic (hyperbranched) or comb-like structures, depending on the method of manufacture. Methods for the manufacture of such materials are generally acid-catalyzed reactions to open the ring of ethyleneimine, also known as aziridine. Examples of suitable polyethyleneimine starting materials for use in the invention have a branched structure comprising three types of subunits, which may be randomly distributed. The subunits which make up the polymer are primary amine units having the formula:
- Branches may be ethyleneamino groups such as - CH2CH2-NH2 groups; or longer groups such as -(CH 2 CH2)-N(CH2CH 2 NH2)2 or -(CH 2 CH2)-N(H)CH2CH 2 NH2 groups.
- the mixture of primary, secondary, and tertiary amine units respectively may be in any molar ratio, including for example in a molar ratio of about 1 :1 :1 to about 1 :2:1.
- the molar ratio of primary, secondary, and tertiary amine units respectively may for example be determined by 13 C-NMR or 15 N-NMR spectroscopy, preferably in D2O.
- D dendritic
- L linear
- T terminal
- DB ranges from 0.25 to 0.95, preferably from 0.30 to 0.80, and more preferably from 0.5 to 0.8.
- each primary or secondary amine hydrogen atom represents a reactive site for subsequent ethoxylation.
- Preferably most or all of such hydrogen atoms are replaced by polyoxyethylene side chains, to form the ethoxylated polyethyleneimine for use in the invention.
- the polyoxyethylene side chains may suitably correspond to the formula R-(EO) n -, in which (EO) n represents an ethylene oxide block; n is a number from 25 to 40, preferably from 25 to 35; and R is hydrogen.
- Preferred polyethyleneimine starting materials in the context of this invention have a primary amine value in the range of from 1 to 1000 mg KOH/g, preferably from 10 to 500 mg KOH/g, most preferred from 50 to 300 mg KOH/g.
- the primary amine value can be determined according to ASTM D2074-07.
- Preferred polyethyleneimine starting materials in the context of this invention have a secondary amine value in the range of from 10 to 1000 mg KOH/g, preferably from 50 to 500 mg KOH/g, most preferred from 50 to 500 mg KOH/g.
- the secondary amine value can be determined according to ASTM D2074-07.
- Preferred polyethyleneimine starting materials in the context of this invention have a tertiary amine value in the range of from 1 to 300 mg KOH/g, preferably from 5 to 200 mg KOH/g, most preferred from 10 to 100 mg KOH/g.
- the tertiary amine value can be determined according to ASTM D2074-07.
- the polyethyleneimine starting material may be pretreated (for example with a
- a standard procedure for the ethoxylation stage involves reacting the polyethyleneimine starting material with at least sufficient ethylene oxide to provide 2-hydroxyethyl groups at each reactive site (i.e. 1 ethylene oxide (EO) group per primary or secondary amine hydrogen atom in the polyethyleneimine molecule).
- the reaction product so obtained is then condensed with the remaining amount of ethylene oxide, typically in the presence of a basic catalyst.
- a preferred procedure for the ethoxylation stage is a two-step procedure requiring the adjustment of the amount of ethylene oxide which is added in the first (and second) step to a certain range.
- This preferred procedure involves reacting, in a first step (1 ), the polyethyleneimine starting material with ethylene oxide in a quantity of significantly less than one molar equivalent, such as in an amount of 0.01 to 0.85, preferably 0.1 to 0.7, more preferably 0.1 to 0.6 and most preferably from 0.1 to 0.5 EO groups per primary or secondary amine hydrogen atom in the polyethyleneimine molecule.
- step (1 ) is carried out in the absence of a catalyst and in an aqueous solution (which may be a solution of from 50 to 99%, preferably from 75 to 99% by weight of the polyethylene starting material in water).
- Step (1 ) may also be carried out in the absence of a catalyst and in the absence of water.
- the temperature during step (1 ) is normally in the range of about 90° to 180°C, preferably 100° to 170°C, more preferably 110° to 160°C and most preferably 120° to 145°C.
- a second step (2) the reaction product obtained from step (1 ), i.e. partially ethoxylated polyethyleneimine, is reacted with the remaining amount of ethylene oxide in the presence of a basic catalyst.
- the second step (2) is preferably carried out at a temperature from 100° to 250 °C, and more preferably 120° to 180° C.
- Suitable basic catalysts include alkali metal (e.g. sodium or potassium) hydroxides; alkali metal (e.g. sodium or potassium) alkoxides such as potassium methylate (KOCH3), potassium tert-butoxide, sodium ethoxide and sodium methylate (NaOCH3); alkali metal or alkaline earth metal hydrides such as sodium hydride and calcium hydride, and alkali metal (e.g. sodium or potassium) carbonates such as sodium carbonate and potassium carbonate. Potassium hydroxide is preferred.
- EPEI ethoxylated polyethyleneimine
- the total degree of ethoxylation per reactive site can be determined according to the following formula: E/(AR), in which E is the total number of moles of ethylene oxide condensed (including hydroxyethylation), A is the number of moles of the polyethyleneimine starting material, and R is the number of reactive sites for the polyethyleneimine starting material.
- Ethoxylated polyethyleneimines (EPEI) for use in the invention may generally have a weight average molecular weight (M w ) of 25000 to 120000 g/mol, preferably 30000 to 100000 g/mol, more preferably 35000 to 90000 g/mol and most preferably from 40000 to 50000 g/mol, determined by gel permeation chromatography (GPC) with 0.05 % by weight potassium trifluoroacetate in hexafluoroisopropanol (HFIP) as eluent and cross- linked polystyrene/divinylbenzene as stationary phase (PL HFIPGel column; MALLS detector).
- M w weight average molecular weight
- Preferred ethoxylated polyethyleneimines for use in the invention correspond to the following general formula (I): [E 2 N-CH2CH2]w[N(E)CH2CH2]x[N(B)CH2CH2]y-NE2 (I) in which E represents a polyoxyethylene side chain corresponding to the formula
- R-(EO) n - as described above; B represents a continuation of the chain structure by branching; w,x and y are each independently from about 1 to 100 and (w + x + y) ranges from about 40 to about 120. Preferably (w + x + y) ranges from about 40 to about 60.
- the subunits making up the polymer of formula (I) may be randomly distributed. Generally, w:x:y ranges from about 1 :1 :1 to about 1 :2:1.
- Particularly preferred ethoxylated polyethyleneimines for use in the invention and corresponding to the above general formula (I) may be produced using the strong under- ethoxylation process as is further described above.
- the level of EPEI (b) preferably ranges from 0.5 to 10%, more preferably from 0.7 to 5% (by weight based on the total weight of the composition).
- laundry detergent in the context of this invention denotes formulated compositions intended for and capable of wetting and cleaning domestic laundry such as clothing, linens and other household textiles.
- the term“linen” is often used to describe certain types of laundry items including bed sheets, pillow cases, towels, tablecloths, table napkins and uniforms.
- Textiles can include woven fabrics, non-woven fabrics, and knitted fabrics; and can include natural or synthetic fibres such as silk fibres, linen fibres, cotton fibres, polyester fibres, polyamide fibres such as nylon, acrylic fibres, acetate fibres, and blends thereof including cotton and polyester blends.
- liquid laundry detergents include heavy-duty liquid laundry detergents for use in the wash cycle of automatic washing machines, as well as liquid fine wash and liquid colour care detergents such as those suitable for washing delicate garments (e.g. those made of silk or wool) either by hand or in the wash cycle of automatic washing machines.
- liquid laundry detergents include heavy-duty liquid laundry detergents for use in the wash cycle of automatic washing machines, as well as liquid fine wash and liquid colour care detergents such as those suitable for washing delicate garments (e.g. those made of silk or wool) either by hand or in the wash cycle of automatic washing machines.
- the term“liquid” in the context of this invention denotes that a continuous phase or predominant part of the composition is liquid and that the composition is flowable at 15°C and above. Accordingly, the term“liquid” may encompass emulsions, suspensions, and compositions having flowable yet stiffer consistency, known as gels or pastes.
- the viscosity of the composition may suitably range from about 200 to about 10,000 mPa.s at 25°C at a
- pourable liquid detergent compositions generally have a viscosity of from 200 to 2,500 mPa.s, preferably from 200 to 1500 mPa.s.
- Liquid detergent compositions which are pourable gels generally have a viscosity of from 1 ,500 mPa.s to 6,000 mPa.s, preferably from 1 ,500 mPa.s to 2,000 mPa.s.
- a composition of the invention may generally comprise from 5 to 95%, preferably from 10 to 90%, more preferably from 15 to 85% water (by weight based on the total weight of the composition).
- the composition may also incorporate non-aqueous carriers such as hydrotropes, co-solvents and phase stabilizers.
- non-aqueous carriers such as hydrotropes, co-solvents and phase stabilizers.
- Such materials are typically low molecular weight, water-soluble or water-miscible organic liquids such as C1 to C5 monohydric alcohols (such as ethanol and n- or i-propanol); C2 to C6 diols (such as monopropylene glycol and dipropylene glycol); C3 to C9 triols (such as glycerol);
- polyethylene glycols having a weight average molecular weight (M w ) ranging from about 200 to 600; C1 to C3 alkanolamines such as mono-, di- and triethanolamines; and alkyl aryl sulfonates having up to 3 carbon atoms in the lower alkyl group (such as the sodium and potassium xylene, toluene, ethylbenzene and isopropyl benzene (cumene) sulfonates).
- M w weight average molecular weight
- C1 to C3 alkanolamines such as mono-, di- and triethanolamines
- alkyl aryl sulfonates having up to 3 carbon atoms in the lower alkyl group (such as the sodium and potassium xylene, toluene, ethylbenzene and isopropyl benzene (cumene) sulfonates).
- Non-aqueous carriers when included, may be present in an amount ranging from 0.1 to 20%, preferably from 1 to 15%, and more preferably from 3 to 12% (by weight based on the total weight of the composition).
- the composition of the invention preferably has a pH in the range of 5 to 9, more preferably 6 to 8, when measured on dilution of the composition to 1 % using
- the composition of the invention comprises from 6 to 50% (by weight based on the total weight of the composition) of one or more detersive surfactants (a) selected from non- soap anionic surfactants, nonionic surfactants and mixtures thereof.
- detersive surfactant in the context of this invention denotes a surfactant which provides a detersive (i.e. cleaning) effect to laundry treated as part of a domestic laundering process.
- Non-soap anionic surfactants for use in the invention are typically salts of organic sulfates and sulfonates having alkyl radicals containing from about 8 to about 22 carbon atoms, the term“alkyl” being used to include the alkyl portion of higher acyl radicals.
- alkyl radicals preferably contain from 10 to 18 carbon atoms and may be unsaturated.
- the alkyl ether sulfates may contain from one to ten ethylene oxide or propylene oxide units per molecule, and preferably contain one to three ethylene oxide units per molecule.
- the counterion for anionic surfactants is generally an alkali metal such as sodium or potassium; or an ammoniacal counterion such as monoethanolamine, (MEA) diethanolamine (DEA) or triethanolamine (TEA). Mixtures of such counterions may also be employed.
- a preferred class of non-soap anionic surfactant for use in the invention includes alkylbenzene sulfonates, particularly linear alkylbenzene sulfonates (LAS) with an alkyl chain length of from 10 to 18 carbon atoms.
- LAS linear alkylbenzene sulfonates
- Commercial LAS is a mixture of closely related isomers and homologues alkyl chain homologues, each containing an aromatic ring sulfonated at the“para” position and attached to a linear alkyl chain at any position except the terminal carbons.
- the linear alkyl chain typically has a chain length of from 1 1 to 15 carbon atoms, with the predominant materials having a chain length of about C12.
- Each alkyl chain homologue consists of a mixture of all the possible sulfophenyl isomers except for the 1 -phenyl isomer.
- LAS is normally formulated into compositions in acid (i.e. HLAS) form and then at least partially neutralized in-situ.
- alkyl ether sulfates having a straight or branched chain alkyl group having 10 to 18, more preferably 12 to 14 carbon atoms and containing an average of 1 to 3EO units per molecule.
- a preferred example is sodium lauryl ether sulfate (SLES) in which the predominantly C12 lauryl alkyl group has been ethoxylated with an average of 3EO units per molecule.
- alkyl sulfate surfactant may be used, such as non-ethoxylated primary and secondary alkyl sulphates with an alkyl chain length of from 10 to 18.
- a preferred mixture of non-soap anionic surfactants for use in the invention comprises linear alkylbenzene sulfonate (preferably Cn to C15 linear alkyl benzene sulfonate) and alkyl ether sulfate (preferably C10 to C18 alkyl sulfate ethoxylated with an average of 1 to 3 EO).
- the total level of non-soap anionic surfactant may suitably range from 5 to 30% (by weight based on the total weight of the composition).
- Nonionic surfactants for use in the invention are typically polyoxyalkylene compounds, i.e. the reaction product of alkylene oxides (such as ethylene oxide or propylene oxide or mixtures thereof) with starter molecules having a hydrophobic group and a reactive hydrogen atom which is reactive with the alkylene oxide.
- Such starter molecules include alcohols, acids, amides or alkyl phenols. Where the starter molecule is an alcohol, the reaction product is known as an alcohol alkoxylate.
- the polyoxyalkylene compounds can have a variety of block and heteric (random) structures. For example, they can comprise a single block of alkylene oxide, or they can be diblock alkoxylates or triblock alkoxylates.
- the blocks can be all ethylene oxide or all propylene oxide, or the blocks can contain a heteric mixture of alkylene oxides.
- examples of such materials include aliphatic alcohol ethoxylates such as Cs to C18 primary or secondary linear or branched alcohol ethoxylates with an average of from 2 to 40 moles of ethylene oxide per mole of alcohol.
- a preferred class of nonionic surfactant for use in the invention includes aliphatic Cs to C18, more preferably C12 to C15 primary linear alcohol ethoxylates with an average of from 3 to 20, more preferably from 5 to 10 moles of ethylene oxide per mole of alcohol.
- the total level of nonionic surfactant may suitably range from 0 to 25% (by weight based on the total weight of the composition).
- a preferred mixture of non-soap anionic and nonionic surfactants for use in the invention comprises linear alkylbenzene sulfonate (preferably Cn to C 15 linear alkyl benzene sulfonate), sodium lauryl ether sulfate (preferably C10 to C18 alkyl sulfate ethoxylated with an average of 1 to 3 EO) and ethoxylated aliphatic alcohol (preferably C12 to C15 primary linear alcohol ethoxylate with an average of from 5 to 10 moles of ethylene oxide per mole of alcohol).
- linear alkylbenzene sulfonate preferably Cn to C 15 linear alkyl benzene sulfonate
- sodium lauryl ether sulfate preferably C10 to C18 alkyl sulfate ethoxylated with an average of 1 to 3 EO
- ethoxylated aliphatic alcohol preferably C12 to C15 primary linear alcohol eth
- composition of the invention may contain further optional ingredients to enhance performance and/or consumer acceptability, as follows:
- a composition of the invention may contain one or more cosurfactants (such as amphoteric (zwitterionic) and/or cationic surfactants) in addition to the non-soap anionic and/or nonionic detersive surfactants described above.
- cosurfactants such as amphoteric (zwitterionic) and/or cationic surfactants
- Specific cationic surfactants include C8 to C18 a ik yi dimethyl ammonium halides and derivatives thereof in which one or two hydroxyethyl groups replace one or two of the methyl groups, and mixtures thereof.
- Cationic surfactant when included, may be present in an amount ranging from 0.1 to 5% (by weight based on the total weight of the composition).
- amphoteric (zwitterionic) surfactants include alkyl amine oxides, alkyl betaines, alkyl amidopropyl betaines, alkyl sulfobetaines (sultaines), alkyl glycinates, alkyl carboxyglycinates, alkyl amphoacetates, alkyl amphopropionates, alkylamphoglycinates, alkyl amidopropyl hydroxysultaines, acyl taurates and acyl glutamates, having alkyl radicals containing from about 8 to about 22 carbon atoms, the term“alkyl” being used to include the alkyl portion of higher acyl radicals.
- Amphoteric (zwitterionic) surfactant when included, may be present in an amount ranging from 0.1 to 5% (by weight based on the total weight of the composition). Mixtures of any of the above described materials may also be used.
- a composition of the invention may contain one or more builders.
- Builders enhance or maintain the cleaning efficiency of the surfactant, primarily by reducing water hardness. This is done either by sequestration or chelation (holding hardness minerals in solution), by precipitation (forming an insoluble substance), or by ion exchange (trading electrically charged particles).
- Builders for use in the invention can be of the organic or inorganic type, or a mixture thereof.
- Suitable inorganic builders include hydroxides, carbonates, sesquicarbonates, bicarbonates, silicates, zeolites, and mixtures thereof. Specific examples of such materials include sodium and potassium hydroxide, sodium and potassium carbonate, sodium and potassium bicarbonate, sodium sesquicarbonate, sodium silicate and mixtures thereof.
- Suitable organic builders include polycarboxylates, in acid and/or salt form.
- alkali metal e.g. sodium and potassium
- alkanolammonium salts are preferred.
- Specific examples of such materials include sodium and potassium citrates, sodium and potassium tartrates, the sodium and potassium salts of tartaric acid monosuccinate, the sodium and potassium salts of tartaric acid disuccinate, sodium and potassium ethylenediaminetetraacetates, sodium and potassium N(2-hydroxyethyl)- ethylenediamine triacetates, sodium and potassium nitrilotriacetates and sodium and potassium N-(2-hydroxyethyl)-nitrilodiacetates.
- Polymeric polycarboxylates may also be used, such as polymers of unsaturated monocarboxylic acids (e.g. acrylic, methacrylic, vinylacetic, and crotonic acids) and/or unsaturated dicarboxylic acids (e.g. maleic, fumaric, itaconic, mesaconic and citraconic acids and their anhydrides).
- unsaturated monocarboxylic acids e.g. acrylic, methacrylic, vinylacetic, and crotonic acids
- unsaturated dicarboxylic acids e.g. maleic, fumaric, itaconic, mesaconic and citraconic acids and their anhydrides.
- unsaturated monocarboxylic acids e.g. acrylic, methacrylic, vinylacetic, and crotonic acids
- unsaturated dicarboxylic acids e.g. maleic, fumaric, itaconic, mesaconic and citraconic acids and their anhydrides.
- the polymers may be in acid, salt or partially neutralised form and may suitably have a molecular weight (Mw) ranging from about 1 ,000 to 100,000, preferably from about 2,000 to about 85,000, and more preferably from about 2,500 to about 75,000 Mixtures of any of the above described materials may also be used.
- Preferred builders for use in the invention may be selected from polycarboxylates (e.g. citrates) in acid and/or salt form and mixtures thereof.
- Builder when included, may be present in an amount ranging from about 0.1 to about 20%, preferably from about 0.5 to about 15%, more preferably from about 1 to about 10% (by weight based on the total weight of the composition).
- Transition metal ion chelating agents
- a composition of the invention may contain one or more chelating agents for transition metal ions such as iron, copper and manganese. Such chelating agents may help to improve the stability of the composition and protect for example against transition metal catalysed decomposition of certain ingredients.
- Suitable transition metal ion chelating agents include phosphonates, in acid and/or salt form. When utilized in salt form, alkali metal (e.g. sodium and potassium) or
- alkanolammonium salts are preferred.
- specific examples of such materials include aminotris(methylene phosphonic acid) (ATMP), 1-hydroxyethylidene diphosphonic acid (HEDP) and diethylenetriamine penta(methylene phosphonic acid (DTPMP) and their respective sodium or potassium salts.
- HEDP is preferred.
- Mixtures of any of the above described materials may also be used.
- Transition metal ion chelating agents when included, may be present in an amount ranging from about 0.1 to about 10%, preferably from about 0.1 to about 3% (by weight based on the total weight of the composition).
- a composition of the invention may in some cases contain one or more fatty acids and/or salts thereof.
- Suitable fatty acids in the context of this invention include aliphatic carboxylic acids of formula RCOOH, where R is a linear or branched alkyl or alkenyl chain containing from 6 to 24, more preferably 10 to 22, most preferably from 12 to 18 carbon atoms and 0 or 1 double bond.
- R is a linear or branched alkyl or alkenyl chain containing from 6 to 24, more preferably 10 to 22, most preferably from 12 to 18 carbon atoms and 0 or 1 double bond.
- saturated C12-18 fatty acids such as lauric acid, myristic acid, palmitic acid or stearic acid
- fatty acid mixtures in which 50 to 100% (by weight based on the total weight of the mixture) consists of saturated C12-18 fatty acids.
- Such mixtures may typically be derived from natural fats and/or optionally hydrogenated natural oils (such as coconut oil, palm kernel oil or tallow).
- the fatty acids may be present in the form of their sodium, potassium or ammonium salts and/or in the form of soluble salts of organic bases, such as mono-, di- or triethanolamine.
- Fatty acids and/or their salts when included, may be present in an amount ranging from about 0.25 to 5%, more preferably from 0.5 to 5%, most preferably from 0.75 to 4% (by weight based on the total weight of the composition).
- fatty acids and/or their salts are not included in the level of surfactant or in the level of builder.
- a composition of the invention will preferably include one or more soil release polymers (SRPs) which help to improve the detachment of soils from fabric by modifying the fabric surface during washing.
- SRPs soil release polymers
- the adsorption of a SRP over the fabric surface is promoted by an affinity between the chemical structure of the SRP and the target fibre.
- SRPs for use in the invention may include a variety of charged (e.g. anionic) as well as non-charged monomer units and structures may be linear, branched or star-shaped.
- the SRP structure may also include capping groups to control molecular weight or to alter polymer properties such as surface activity.
- the weight average molecular weight (M w ) of the SRP may suitably range from about 1000 to about 20,000 and preferably ranges from about 1500 to about 10,000.
- SRPs for use in the invention may suitably be selected from copolyesters of dicarboxylic acids (for example adipic acid, phthalic acid or terephthalic acid), diols (for example ethylene glycol or propylene glycol) and polydiols (for example polyethylene glycol or polypropylene glycol).
- the copolyester may also include monomeric units substituted with anionic groups, such as for example sulfonated isophthaloyl units.
- oligomeric esters produced by transesterification/oligomerization of poly(ethyleneglycol) methyl ether, dimethyl terephthalate (“DMT”), propylene glycol (“PG”) and poly(ethyleneglycol) (“PEG”); partly- and fully-anionic-end-capped oligomeric esters such as oligomers from ethylene glycol (“EG”), PG, DMT and Na-3,6-dioxa-8- hydroxyoctanesulfonate; nonionic-capped block polyester oligomeric compounds such as those produced from DMT, Me-capped PEG and EG and/or PG, or a combination of DMT, EG and/or PG, Me-capped PEG and Na-dimethyl-5-sulfoisophthalate, and copolymeric blocks of ethylene terephthalate or propylene terephthalate with polyethylene oxide or polypropylene oxide terephthalate
- cellulosic derivatives such as hydroxyether cellulosic polymers, Ci-C4 alkylcelluloses and C 4 hydroxyalkyl celluloses
- Preferred SRPs for use in the invention include copolyesters formed by condensation of terephthalic acid ester and diol, preferably 1 ,2 propanediol, and further comprising an end cap formed from repeat units of alkylene oxide capped with an alkyl group. Examples of such materials have a structure corresponding to general formula (I):
- R 1 and R 2 independently of one another are X-(OC2H4) n -(OC3H6) m ;
- X is C1-4 alkyl and preferably methyl
- n is a number from 12 to 120, preferably from 40 to 50;
- n is a number from 1 to 10, preferably from 1 to 7; and a is a number from 4 to 9.
- n, n and a are not necessarily whole numbers for the polymer in bulk.
- a composition of the invention will generally comprise from 0.1 to 10%, preferably from 0.3 to 7%, more preferably from 0.5 to 5% (by weight based on the total weight of the composition) of one or more SRPs (such as, for example, the copolyesters of general formula (I) as are described above).
- SRPs such as, for example, the copolyesters of general formula (I) as are described above.
- a composition of the invention may comprise one or more rheology modifiers.
- examples of such materials include polymeric thickeners and/or structurants such as
- HASE copolymers for use in the invention include linear or crosslinked copolymers that are prepared by the addition polymerization of a monomer mixture including at least one acidic vinyl monomer, such as (meth)acrylic acid (i.e. methacrylic acid and/or acrylic acid); and at least one associative monomer.
- acidic vinyl monomer such as (meth)acrylic acid (i.e. methacrylic acid and/or acrylic acid); and at least one associative monomer.
- associative monomer in the context of this invention denotes a monomer having an ethylenically unsaturated section (for addition polymerization with the other monomers in the mixture) and a hydrophobic section.
- a preferred type of associative monomer includes a polyoxyalkylene section between the ethylenically unsaturated section and the hydrophobic section.
- Preferred HASE copolymers for use in the invention include linear or crosslinked copolymers that are prepared by the addition polymerization of (meth)acrylic acid with (i) at least one associative monomer selected from linear or branched C8-C40 alkyl (preferably linear C12- C22 alkyl) polyethoxylated (meth)acrylates; and (ii) at least one further monomer selected from C1-C4 alkyl (meth) acrylates, polyacidic vinyl monomers (such as maleic acid, maleic anhydride and/or salts thereof) and mixtures thereof.
- the polyethoxylated portion of the associative monomer (i) generally comprises about 5 to about 100, preferably about 10 to about 80, and more preferably about 15 to about 60 oxyethylene repeating units.
- compositions of the invention will preferably comprise from 0.1 to 5% (by weight based on the total weight of the composition) of one or more polymeric thickeners such as, for example, the HASE copolymers which are described above.
- compositions of the invention may also have their rheology modified by use of one or more external structurants which form a structuring network within the composition.
- Examples of such materials include hydrogenated castor oil, microfibrous cellulose and citrus pulp fibre.
- the presence of an external structurant may provide shear thinning rheology and may also enable materials such as encapsulates and visual cues to be suspended stably in the liquid.
- a composition of the invention may comprise an effective amount of one or more enzyme selected from the group comprising, pectate lyase, protease, amylase, cellulase, lipase, mannanase and mixtures thereof.
- the enzymes are preferably present with
- a composition of the invention may contain further optional ingredients to enhance performance and/or consumer acceptability.
- additional optional ingredients include foam boosting agents, preservatives (e.g. bactericides), polyelectrolytes, anti-shrinking agents, anti-wrinkle agents, anti-oxidants, sunscreens, anti-corrosion agents, drape imparting agents, anti-static agents, ironing aids, colorants, pearlisers and/or opacifiers, and shading dye.
- foam boosting agents e.g. bactericides
- preservatives e.g. bactericides
- polyelectrolytes e.g. bactericides
- anti-shrinking agents e.g. bactericides
- anti-wrinkle agents e.g. bactericides
- anti-oxidants e.g. s, sunscreens, anti-corrosion agents, drape imparting agents, anti-static agents, ironing aids, colorants, pearlisers and/or opacifiers, and shading dye.
- a composition of the invention may be packaged as unit doses in polymeric film soluble in the wash water.
- a composition of the invention may be supplied in multidose plastics packs with a top or bottom closure.
- a dosing measure may be supplied with the pack either as a part of the cap or as an integrated system.
- a method of laundering fabric using a composition of the invention will usually involve diluting the dose of detergent composition to obtain a wash liquor, and washing fabrics with the wash liquor so formed.
- the method of laundering fabric may suitably be carried out in a top-loading or front-loading automatic washing machine, or can be carried out by hand.
- the dose of detergent composition is typically put into a dispenser and from there it is flushed into the machine by the water flowing into the machine, thereby forming the wash liquor.
- Dosages for a typical front-loading washing machine (using 10 to 15 litres of water to form the wash liquor) may range from about 10 ml to about 100 ml, preferably about 15 to 75 ml.
- Dosages for a typical top-loading washing machine (using from 40 to 60 litres of water to form the wash liquor) may be higher, e.g. 100 ml or more.
- Lower dosages of detergent e.g. 50 ml or less
- hand washing methods using about 1 to 10 litres of water to form the wash liquor).
- a subsequent aqueous rinse step and drying the laundry is preferred.
- G EPEI with polyethyleneimine backbone derived from a polyethyleneimine starting material having an average molecular weight (M w ) of 1300 g/mol (prior to ethoxylation), and polyoxyethylene side chains having an average of 25 ethoxy units per side chain bonded to the polyethyleneimine backbone;
- E EPEI with polyethyleneimine backbone derived from a polyethyleneimine starting material having an average molecular weight (M w ) of 2000 g/mol (prior to ethoxylation), and polyoxyethylene side chains having an average of 20 ethoxy units per side chain bonded to the polyethyleneimine backbone;
- Liquid laundry detergent formulations were prepared using different grades of EPEI in a HASE thickened liquid detergent base. The formulations are shown in Table 3. Table 3
- Example 10 using EPEI prepared by the preferred ethoxylation process provides particularly good results, with a viscosity
- Example 9 which uses an EPEI of equivalent backbone size and degree of ethoxylation, but prepared by a standard process.
- Example 12 using EPEI prepared by the preferred ethoxylation process provides particularly good results, with a viscosity
- Example 1 1 which uses an EPEI of equivalent backbone size and degree of ethoxylation, but prepared by a standard process.
- Liquid laundry detergent formulations were prepared using different grades of EPEI in a salt thickened detergent base. The formulations are shown in Table 4.
- Example 13 has a superior product viscosity compared to both the control and Example G (not according to the invention).
- Liquid laundry detergent formulations were prepared using different grades of EPEI in a salt thickened detergent base. The formulations are shown in Table 5.
- Examples 14 to 17 have a superior product viscosity compared to Example H (not according to the invention). It can also be seen how Example 15 using EPEI prepared by the preferred ethoxylation process (described above) provides particularly good results, with a viscosity
- Example 14 which uses an EPEI of equivalent backbone size and degree of ethoxylation, but prepared by a standard process.
- Example 17 using EPEI prepared by the preferred ethoxylation process provides particularly good results, with a viscosity
- Example 15 which uses an EPEI of equivalent backbone size and degree of ethoxylation, but prepared by a standard process.
- Liquid laundry detergent formulations were prepared having ingredients as shown in Table 6.
- the cleaning performance of the above formulations was evaluated across a variety of stains on white test cloths of cotton or polyester.
- the stained test cloths were washed using a 30ml dosage of test formulation in the 40°C cotton cycle of an automatic washing machine with a water supply of 26°FH. - 21
- After-wash SRI 100 - DE where DE is the difference in colour of the stained test cloth compared to an unstained control cloth. A higher SRI value indicates cleaner cloths.
- Example 18 is at least equivalent to that of Example I (not according to the invention).
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Abstract
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CN201980053706.5A CN112567011B (zh) | 2018-08-10 | 2019-08-08 | 洗涤剂 |
ES19748851T ES2910348T3 (es) | 2018-08-10 | 2019-08-08 | Detergente |
EP19748851.3A EP3833730B1 (fr) | 2018-08-10 | 2019-08-08 | Détergent |
BR112021001856-5A BR112021001856A2 (pt) | 2018-08-10 | 2019-08-08 | composição detergente líquida para lavanderia e método para lavagem de tecidos |
ZA2021/00792A ZA202100792B (en) | 2018-08-10 | 2021-02-04 | Detergent |
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EP18188543.5 | 2018-08-10 | ||
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CN (1) | CN112567011B (fr) |
BR (1) | BR112021001856A2 (fr) |
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Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022122425A1 (fr) | 2020-12-07 | 2022-06-16 | Unilever Ip Holdings B.V. | Composition |
WO2023198434A1 (fr) * | 2022-04-14 | 2023-10-19 | Basf Se | Compositions, leur fabrication et leur utilisation |
EP4321604A1 (fr) | 2022-08-08 | 2024-02-14 | The Procter & Gamble Company | Tissu et composition de soins à domicile comprenant un tensioactif et un polyester |
WO2024094803A1 (fr) | 2022-11-04 | 2024-05-10 | The Procter & Gamble Company | Composition d'entretien textile et ménager |
WO2024094800A1 (fr) | 2022-11-04 | 2024-05-10 | The Procter & Gamble Company | Composition d'entretien textile et ménager |
WO2024094802A1 (fr) | 2022-11-04 | 2024-05-10 | The Procter & Gamble Company | Tissu et composition d'entretien ménager |
WO2024119298A1 (fr) | 2022-12-05 | 2024-06-13 | The Procter & Gamble Company | Composition de soin textile et ménager comprenant un composé de carbonate de polyalkylène |
EP4386074A1 (fr) | 2022-12-16 | 2024-06-19 | The Procter & Gamble Company | Composition de soin pour le linge et le domicile |
WO2024129520A1 (fr) | 2022-12-12 | 2024-06-20 | The Procter & Gamble Company | Composition de soin textile et ménager |
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CN113773917A (zh) * | 2021-08-26 | 2021-12-10 | 广东湛丰精细化工有限公司 | 一种基于改性纳米陶土的精炼除油剂及其制备方法 |
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- 2019-08-08 ES ES19748851T patent/ES2910348T3/es active Active
- 2019-08-08 WO PCT/EP2019/071369 patent/WO2020030760A1/fr unknown
- 2019-08-08 CN CN201980053706.5A patent/CN112567011B/zh active Active
- 2019-08-08 EP EP19748851.3A patent/EP3833730B1/fr active Active
- 2019-08-08 BR BR112021001856-5A patent/BR112021001856A2/pt active Search and Examination
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WO2023198434A1 (fr) * | 2022-04-14 | 2023-10-19 | Basf Se | Compositions, leur fabrication et leur utilisation |
EP4321604A1 (fr) | 2022-08-08 | 2024-02-14 | The Procter & Gamble Company | Tissu et composition de soins à domicile comprenant un tensioactif et un polyester |
WO2024036126A1 (fr) | 2022-08-08 | 2024-02-15 | The Procter & Gamble Company | Tissu et composition d'entretien de la maison comprenant un tensioactif et un polyester |
WO2024094803A1 (fr) | 2022-11-04 | 2024-05-10 | The Procter & Gamble Company | Composition d'entretien textile et ménager |
WO2024094800A1 (fr) | 2022-11-04 | 2024-05-10 | The Procter & Gamble Company | Composition d'entretien textile et ménager |
WO2024094802A1 (fr) | 2022-11-04 | 2024-05-10 | The Procter & Gamble Company | Tissu et composition d'entretien ménager |
WO2024119298A1 (fr) | 2022-12-05 | 2024-06-13 | The Procter & Gamble Company | Composition de soin textile et ménager comprenant un composé de carbonate de polyalkylène |
WO2024129520A1 (fr) | 2022-12-12 | 2024-06-20 | The Procter & Gamble Company | Composition de soin textile et ménager |
EP4386074A1 (fr) | 2022-12-16 | 2024-06-19 | The Procter & Gamble Company | Composition de soin pour le linge et le domicile |
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ZA202100792B (en) | 2022-08-31 |
CN112567011A (zh) | 2021-03-26 |
BR112021001856A2 (pt) | 2021-05-04 |
ES2910348T3 (es) | 2022-05-12 |
CN112567011B (zh) | 2022-04-15 |
EP3833730B1 (fr) | 2022-02-16 |
EP3833730A1 (fr) | 2021-06-16 |
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