WO2021074547A1 - Alcoxylats à pouvoir hydrotrope amélioré - Google Patents
Alcoxylats à pouvoir hydrotrope amélioré Download PDFInfo
- Publication number
- WO2021074547A1 WO2021074547A1 PCT/FR2020/051859 FR2020051859W WO2021074547A1 WO 2021074547 A1 WO2021074547 A1 WO 2021074547A1 FR 2020051859 W FR2020051859 W FR 2020051859W WO 2021074547 A1 WO2021074547 A1 WO 2021074547A1
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- WIPO (PCT)
- Prior art keywords
- secondary alcohol
- octanol
- units
- chosen
- formulation
- Prior art date
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- 230000003165 hydrotropic effect Effects 0.000 title claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 60
- 238000009472 formulation Methods 0.000 claims abstract description 56
- 150000003333 secondary alcohols Chemical class 0.000 claims abstract description 56
- 239000004094 surface-active agent Substances 0.000 claims abstract description 25
- 239000003599 detergent Substances 0.000 claims abstract description 14
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims description 72
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 23
- 238000004140 cleaning Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 238000006555 catalytic reaction Methods 0.000 claims description 11
- 239000000945 filler Substances 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 6
- 125000006353 oxyethylene group Chemical group 0.000 claims description 6
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- -1 oxybutylene Chemical group 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 2
- 150000002334 glycols Chemical class 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 239000012178 vegetable wax Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000002736 nonionic surfactant Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000466 oxiranyl group Chemical group 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000013011 aqueous formulation Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-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
- 241000609240 Ambelania acida Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 description 1
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 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 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical group OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005157 alkyl carboxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- NHNBRUZMOBULPD-UHFFFAOYSA-N azanium;4-hydroxy-4-oxo-3-sulfobutanoate Chemical compound N.OC(=O)CC(C(O)=O)S(O)(=O)=O NHNBRUZMOBULPD-UHFFFAOYSA-N 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GNKKSLPLBNHOMG-UHFFFAOYSA-L calcium;2-sulfobutanedioate Chemical compound [Ca+2].OS(=O)(=O)C(C([O-])=O)CC([O-])=O GNKKSLPLBNHOMG-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000005202 decontamination Methods 0.000 description 1
- 230000003588 decontaminative effect Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000002761 deinking Substances 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- BLSNQVPBJDBAJJ-UHFFFAOYSA-L dipotassium;2-sulfobutanedioate Chemical compound [K+].[K+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O BLSNQVPBJDBAJJ-UHFFFAOYSA-L 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012978 lignocellulosic material Substances 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000000080 wetting agent 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
- C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2651—Alkaline earth metals or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele 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
- 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
Definitions
- the present invention relates to the general field of formulations containing surfactants, more particularly that of formulations containing nonionic surfactants and in particular that of formulations containing alkoxylated nonionic surfactants.
- alkoxylated compounds represent a family of compounds offering a wide range of properties, with multiple applications, such as solvents, hydrotropic agents or even surfactants, to name a few. between them.
- alkoxylated compounds constitute a class of compounds with surface-active properties which is of real industrial interest in a very large number of fields of application.
- alkoxylated compounds as surfactants constitute a very privileged application, as the volumes of surfactants are today large for such numerous and varied uses, and for example in the form of formulations for detergency or cleaning or washing to name a few examples.
- the surfactants make it possible, because of their intrinsic properties, to make the soiling which is most often organic and lipophilic, compatible with a hydrophilic medium, generally an aqueous medium, and so to be able to remove said lipophilic soiling with the hydrophilic medium.
- a hydrophilic medium generally an aqueous medium
- surfactants can present problems of solubility with the media in which they are used, so that it is often necessary to add one or more surfactant solubilizers.
- hydrotropic agents are generally used.
- a hydrotropic agent is a compound which dissolves hydrophobic compounds in aqueous solutions. Hydrotropic agents are now commonly used industrially in the formulation of detergents, in particular to make it possible to have a greater concentration of surfactants.
- multi-purpose cleaners in English
- cosmetic products cleaning of hard surfaces
- Hard Surface Cleaning in English
- cleaning clothes cleaning toilets
- washing cars in general
- Cleaning In Place CIP
- CIP Cleaning In Place
- Such alkoxylated nonionic surfactants are for example described in international application WO2009000852, said surfactants being alcohol alkoxylates of the Neodol type (polybranched alcohols obtained by the Fischer-Tropsch process) and of the primary type.
- Nonionic alkoxylated surfactants such as for example those described in the documents cited above, however have often insufficient hydrotropic powers, so that today there remains a need for formulations for detergency at based on nonionic surfactants with even greater or even significant hydrotropic powers.
- Another objective of the present invention is to provide formulations for detergency based on surfactants with improved hydrotropic power, and which are derived from bio-sourced products, and more particularly from bio-sourced products which do not enter not in competition with the human or animal food sector.
- the present invention relates to a formulation for detergency comprising at least one secondary alcohol alkoxylate, in which said secondary alcohol comprises from 3 to 22 carbon atoms, preferably from 5 to 22 atoms.
- oxyalkylene units chosen from oxyethylene (EO), oxypropylene (OP) and oxybutylene (OB), the total number of oxyalkylene units being between 2 and 100, preferably between 3 and 100, more preferably between 3 and 50, better still between 3 and 40, and very particularly between 3 and 30 , terminals included.
- EO oxyethylene
- OP oxypropylene
- OB oxybutylene
- the oxyalkylene units of the secondary alcohol alkoxylate can be the same or different and, if they are different, they can be arranged in any way and for example randomly, in blocks, in an alternating manner or sequenced or otherwise. It is particularly preferred to use, for the purposes of the present invention, a secondary alcohol alkoxylate as defined above and having oxyalkylene units arranged in blocks.
- the alcohol used as the starting substrate for the alkoxylation reaction (s) has a degree of branching equal to 0, 1 or 2, more preferably 1 or 2.
- degree of branching denoted by D is an integer equal to the difference between the sum of the end groups present on the alcohol used as the starting substrate for the alkoxylation reaction (s) and 1.
- the branching degree of cardanol (1 terminal methylene group) is 0, that of 2-octanol is 1, and that of 4-methyl-2-pentanol is 2.
- the alcohol used as the starting substrate for the reaction (s) of alkoxylation comprises from 3 to 22, preferably from 5 to 22 carbon atoms, more preferably from 5 to 20 , very particularly preferably from 5 to 18 carbon atoms.
- the carbon atoms can be straight chain, branched or partly or totally cyclic.
- the secondary alcohol has an average molar mass by weight ranging from 45 g mol 1 to 300 g mol 1 , preferably from 70 g mol 1 to 250 g mol 1 , more preferably from 80 g mol 1 at 200 g mol 1 , terminals included.
- the secondary alcohol used as a starting substrate and intended to be alkoxylated can be of any type and all origins, and in particular of petroleum origin, or of bio-sourced origin, for example of plant or animal origin. .
- a secondary alcohol of bio-sourced origin is preferred, for obvious reasons of environmental protection.
- a secondary alcohol comprising from 3 to 14 carbon atoms, more preferably from 6 to 12 carbon atoms, is also preferred, and according to a very particularly preferred embodiment the secondary alcohol is chosen from 2-octanol and 4-methyl-2-pentanol, very particularly advantageously, the secondary alcohol is 2-octanol.
- 2-octanol is in fact of particular interest in several respects, in particular because it comes from a bio-sourced product and which does not compete with human or animal food.
- 2-octanol which has a high boiling point, is biodegradable and has a good ecotoxicological profile.
- the alkoxylated repeating units are chosen from the units of ethylene oxide, propylene oxide, butylene oxide, and mixtures thereof.
- ethylene oxide unit means a unit derived from ethylene oxide after opening of the oxirane ring
- propylene oxide unit means a unit derived from propylene oxide after opening of the oxirane ring
- butylene oxide unit means a unit derived from butylene oxide after opening of the oxirane ring.
- alkylene oxides mentioned above can be of various origins, and in particular alkylene oxides "mass balance", in particular ethylene oxide "mass balance", alkylene oxides of bio-sourced origin.
- ethylene oxide is of bio-sourced origin, for example ethylene oxide can be obtained by oxidation of bio-sourced ethylene originating from the dehydration of bio-ethanol, itself originating from starch. corn, lignocellulosic materials, agricultural residues such as, for example, sugar cane bagasse, and the like.
- the secondary alcohol alkoxylate as it has just been defined and useful for the preparation of formulations for detergency with improved hydrotrope power according to the present invention can be prepared according to any means known to those skilled in the art, and in particular according to any known method of alcohol alkoxylation.
- the alkoxylation of alcohol is advantageously carried out in the presence of a catalyst, and the alkoxylation is advantageously carried out by basic or alkaline catalysis, for example using sodium hydroxide (NaOH) or l potassium hydroxide (KOH), known as soda or potash catalysis, respectively.
- catalysts can be used and in particular those now known to those skilled in the art specializing in alkoxylation to lead to alkoxylates having a distribution in number of alkoxylate units that is narrow, or even very narrow.
- Such catalysts are known under the name of “narrow range” catalysts, and are for example chosen from calcium-based catalysts, based on boron-based derivatives (such as acid catalysts of the type derived from BF 3 ), catalysts of hydrotalcite type, and catalysts of dimetallic cyanide type (“DiMetallic Cyanide” in English, or DMC).
- the formulation in which said at least one secondary alcohol alkoxylate is chosen from narrowly distributed secondary alcohol alkoxylates and in particular those obtained by alkoxylation of a secondary alcohol via narrow range catalysis, and more preferably via DMC catalysis.
- the secondary alcohol alkoxylate used as a surfactant with improved hydrotropic power in the formulation for detergency according to the present invention is a capped (or capped) secondary alcohol alkoxylate, that is to say in which the terminal —OH part is substituted, as described for example in document EP2205711, or alternatively in international application WO2004037960.
- the substituent of the terminal part is a group chosen from linear or branched alkyls comprising from 1 to 6 carbon atoms, the phenyl group , the benzyl group, the hydrocarbon groups carrying a carboxy -COO- function, and the groups carrying a sugar unit.
- the end cap of the secondary alcohol alkoxylate is chosen from methyl, ethyl, propyl, butyl, benzyl and alkylcarboxyl groups and its salts.
- the possible salts of the carboxyl function there may be mentioned the salts well known to those skilled in the art and in particular the salts of metals, alkali metals, alkaline earth metals, ammonium, to name only the main of them.
- Particularly preferred salts are the sodium, potassium, calcium and ammonium salts.
- the end cap of the secondary alcohol alkoxylate is chosen from alkylenecarboxyls and their salts, optionally functionalized.
- a typical and non-limiting example is represented by the sulfosuccinate group, and in particular sodium sulfosuccinate, potassium sulfosuccinate, calcium sulfosuccinate and ammonium sulfosuccinate.
- the end cap of the secondary alcohol alkoxylate is chosen from groups carrying a sugar unit, such as for example glucose (case of monoglucosides), or two or more sugar units (case of alkypolyglucosides, also called “APG”).
- a sugar unit such as for example glucose (case of monoglucosides), or two or more sugar units (case of alkypolyglucosides, also called “APG”).
- formulations for detergency in which said at least one secondary alcohol alkoxylate comprises at least ethylene oxide (EO) units.
- the formulation for detergency comprises at least one secondary alcohol alkoxylate having at least ethylene oxide (EO) units and at least propylene oxide (OP) units, said patterns which can be distributed randomly, alternately or in blocks, and preferably in blocks.
- the total number of repeating units carried by the secondary alcohol alkoxylate included in the formulation for detergency according to the present invention is between, limits included, 1 and 30, preferably between 2 and 20, more preferably between 3 and 20, advantageously between 3 and 15.
- the formulation for detergency according to the present invention comprises at least one 2-octanol alkoxylate.
- said alkoxylate is chosen from 2-octanol with ethoxylated units, 2-octanol with ethoxylated and propoxylated units, 2-octanol with ethoxylated and butoxylated units, 2-octanol with propoxylated units, 2- octanol with propoxylated and butoxylated units, and 2-octanol with butoxylated units.
- detergency formulations comprising at least one 2-octanol with ethoxylated units or at least one 2-octanol with ethoxylated and propoxylated units are preferred.
- secondary alcohol alkoxylates which are very particularly suitable for the formulations according to the present invention are those chosen from 2-octanol 2-15 EO, 2-octanol 2-15 EO 1 PO, 2 -octanol 2-15 EO 1-15 OB, 2-octanol 2-15 EO 1 -15 OP, and 2-octanol 1 -6 EO 1 -15 OP.
- the formulation according to the present invention can comprise any type of additives, fillers known to those skilled in the art of formulations and in particular formulations for detergents.
- the formulation for detergency according to the present invention may comprise one or more of the additives and fillers chosen from detergency agents, in particular basic, such as for example sodium hydroxide, surfactants, perfumes, dyes, inert fillers, impregnating agents, aqueous, organic, hydro-organic solvents, chosen from water, alcohols, glycols, polyols, mineral oils, vegetable oils, waxes, and the like, alone or as mixtures of two or more of them, in all proportions.
- detergency agents in particular basic, such as for example sodium hydroxide, surfactants, perfumes, dyes, inert fillers, impregnating agents, aqueous, organic, hydro-organic solvents, chosen from water, alcohols, glycols, polyols, mineral oils, vegetable oils, waxes, and the like, alone or as mixtures of two or more of them, in all proportions.
- the formulation according to the invention may comprise one or more additives and fillers well known to those skilled in the art, such as, for example, and without limitation, anionic, cationic, amphoteric or non-limiting surfactants.
- additives and fillers can vary widely depending on the nature of the application envisaged and can easily be adapted by those skilled in the art.
- the formulation for detergency according to the present invention comprises a secondary alcohol alkoxylate as it has just been defined with improved hydrotropic power, thus giving the formulation which contains it quite advantageous properties, in particular in terms of solubilization, but also in terms of detergent power. It has in fact been observed that the formulations of the present invention and in particular those comprising a 2-octanol alkoxylate exhibit improved detergency power, in particular due to the high hydrotropic power of the secondary alcohol alkoxylate. Finally, a subject of the present invention is the use of at least one secondary alcohol alkoxylate, as a surfactant with improved hydrotropic power, in a detergent formulation.
- the secondary alcohol alkoxylates as they have just been defined, and in particular those obtained by “narrow range” catalysis thus find very suitable applications because of their very good degreasing, solubilizing and emulsifying properties. , and in particular because of their improved hydrotropic power, which makes them surfactants of choice when used in dishwashing detergent formulations. In fact, improved hydrotropic power generally leads to better results in terms of "spotting", that is to say traces left on dishes and in particular glass.
- the secondary alcohol alkoxylates as they have just been defined find quite interesting applications in detergent formulations, and in particular in detergent formulations for dishwashers, for multi-purpose cleaning ( “Multi-purpose cleaner” in English), for cleaning hard surfaces ("Hard Surface Cleaning” in English), for cleaning clothes ("laundry” in English), for cosmetic products, for sanitary cleaning, for car washing in general, for Cleaning In Place (CIP) or “cleaning in place” in English (CIP), and others.
- Secondary alcohol alkoxylates as defined above can also be used in various formulations in which such surfactants are necessary or desired as emulsifier, wetting agents, solvents or adjuvants, and in particular in formulations for the flotation of ores, for the treatment of metals ("Metal Working Fluids" in English), for bituminous applications, for deinking, for enhanced gas and oil recovery applications, for protection against corrosion, for hydraulic fracturing, for soil decontamination, in agrochemistry (for example coatings for granular products, in particular fertilizers and phytosanitary products), but also as an anti-foam agent, antistatic agent, paint adjuvant, textile adjuvant, for polyols, for the production of electrodes and electrolytes for batteries, to name only the main fields of application.
- the invention is now illustrated by the following examples which are in no way limiting.
- the characterization of the hydrotropic power of a product to be tested consists in heating a solution containing a reference product and noting the temperature of disappearance of the cloudiness formed by the desolubilization of the reference product in the solution.
- the hydrotropic power corresponds to this temperature (expressed in ° C). The higher this temperature, the more hydrotropic the product.
- the present invention therefore provides a simple and effective solution making it possible in particular to increase the concentration of surfactants in formulations for detergents, while retaining a clear and perfectly homogeneous appearance, this solution consisting in adding at least one alkoxylate secondary alcohol in said detergency formulation.
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Abstract
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Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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EP20803631.9A EP4045624A1 (fr) | 2019-10-18 | 2020-10-16 | Alcoxylats à pouvoir hydrotrope amélioré |
US17/769,135 US20240110128A1 (en) | 2019-10-18 | 2020-10-16 | Alkoxylates having improved hydrotropic power |
CN202080072953.2A CN114599770A (zh) | 2019-10-18 | 2020-10-16 | 具有改善的水溶助长能力的烷氧基化物 |
JP2022522885A JP2022552998A (ja) | 2019-10-18 | 2020-10-16 | 改善されたヒドロトロープ力を有するアルコキシレート |
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FRFR1911678 | 2019-10-18 | ||
FR1911678A FR3102174A1 (fr) | 2019-10-18 | 2019-10-18 | Alcoxylats à pouvoir hydrotrope amélioré |
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US (1) | US20240110128A1 (fr) |
EP (1) | EP4045624A1 (fr) |
JP (1) | JP2022552998A (fr) |
CN (1) | CN114599770A (fr) |
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2014933A1 (fr) * | 1968-08-02 | 1970-04-24 | Procter & Gamble | |
WO2001079401A1 (fr) * | 2000-04-18 | 2001-10-25 | Cognis Deutschland Gmbh & Co. Kg | Detergents et nettoyants |
WO2004037960A1 (fr) | 2002-10-24 | 2004-05-06 | Kao Corporation, S.A. | Utilisation d'ether carboxylates comme lubrifiants |
WO2009000852A1 (fr) | 2007-06-27 | 2008-12-31 | Shell Internationale Research Maatschappij B.V. | Composition d'alcoxylate et son procédé de préparation |
EP2205711A1 (fr) | 2007-10-15 | 2010-07-14 | Chemteall GmbH | Composition nettoyante pour surfaces métalliques |
WO2012005897A1 (fr) | 2010-06-29 | 2012-01-12 | Dow Global Technologies Llc | Tensioactifs de type alkoxylate d'alcools secondaires ramifiés et leur procédé de fabrication |
WO2019092366A1 (fr) | 2017-11-10 | 2019-05-16 | Arkema France | Alcool secondaire alcoxylé |
-
2019
- 2019-10-18 FR FR1911678A patent/FR3102174A1/fr active Pending
-
2020
- 2020-10-16 EP EP20803631.9A patent/EP4045624A1/fr active Pending
- 2020-10-16 US US17/769,135 patent/US20240110128A1/en active Pending
- 2020-10-16 CN CN202080072953.2A patent/CN114599770A/zh active Pending
- 2020-10-16 JP JP2022522885A patent/JP2022552998A/ja active Pending
- 2020-10-16 WO PCT/FR2020/051859 patent/WO2021074547A1/fr active Application Filing
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2014933A1 (fr) * | 1968-08-02 | 1970-04-24 | Procter & Gamble | |
WO2001079401A1 (fr) * | 2000-04-18 | 2001-10-25 | Cognis Deutschland Gmbh & Co. Kg | Detergents et nettoyants |
WO2004037960A1 (fr) | 2002-10-24 | 2004-05-06 | Kao Corporation, S.A. | Utilisation d'ether carboxylates comme lubrifiants |
WO2009000852A1 (fr) | 2007-06-27 | 2008-12-31 | Shell Internationale Research Maatschappij B.V. | Composition d'alcoxylate et son procédé de préparation |
EP2205711A1 (fr) | 2007-10-15 | 2010-07-14 | Chemteall GmbH | Composition nettoyante pour surfaces métalliques |
WO2012005897A1 (fr) | 2010-06-29 | 2012-01-12 | Dow Global Technologies Llc | Tensioactifs de type alkoxylate d'alcools secondaires ramifiés et leur procédé de fabrication |
WO2019092366A1 (fr) | 2017-11-10 | 2019-05-16 | Arkema France | Alcool secondaire alcoxylé |
Non-Patent Citations (1)
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BIG SUN CHEM CORP: "Tergitol 15-S-9 Surfactant", 1 January 2001 (2001-01-01), XP055705737, Retrieved from the Internet <URL:http://www.bigsunchem.com.tw/image/tergitol15-s-9.pdf> [retrieved on 20200617] * |
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JP2022552998A (ja) | 2022-12-21 |
US20240110128A1 (en) | 2024-04-04 |
FR3102174A1 (fr) | 2021-04-23 |
CN114599770A (zh) | 2022-06-07 |
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