EP3818137A1 - Aktivstoffe für hochviskose wasch- und reinigungsformulierungen - Google Patents
Aktivstoffe für hochviskose wasch- und reinigungsformulierungenInfo
- Publication number
- EP3818137A1 EP3818137A1 EP19734091.2A EP19734091A EP3818137A1 EP 3818137 A1 EP3818137 A1 EP 3818137A1 EP 19734091 A EP19734091 A EP 19734091A EP 3818137 A1 EP3818137 A1 EP 3818137A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- particularly preferably
- general formula
- washing
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 107
- 238000009472 formulation Methods 0.000 title claims abstract description 67
- 239000013543 active substance Substances 0.000 title claims abstract description 49
- 238000004140 cleaning Methods 0.000 title claims abstract description 40
- 238000005406 washing Methods 0.000 title claims abstract description 40
- 239000002979 fabric softener Substances 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 32
- 239000000194 fatty acid Substances 0.000 claims description 32
- 229930195729 fatty acid Natural products 0.000 claims description 32
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 21
- 229910052740 iodine Inorganic materials 0.000 claims description 21
- 239000011630 iodine Substances 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 239000003760 tallow Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 229940100198 alkylating agent Drugs 0.000 claims description 6
- 239000002168 alkylating agent Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 5
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 claims description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- 235000013311 vegetables Nutrition 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 claims description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 229960004063 propylene glycol Drugs 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims 1
- 239000002562 thickening agent Substances 0.000 abstract description 12
- 239000012459 cleaning agent Substances 0.000 abstract 1
- 239000003599 detergent Substances 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 239000002304 perfume Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 150000002191 fatty alcohols Chemical class 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- 150000003868 ammonium compounds Chemical class 0.000 description 3
- -1 bis (2-hydroxypropyl) dimethylammonium methyl sulfate fatty acid esters Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000004176 azorubin Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003974 emollient agent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000000077 insect repellent Substances 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- DJYWKXYRGAMLRE-QXMHVHEDSA-N (z)-icos-9-en-1-ol Chemical compound CCCCCCCCCC\C=C/CCCCCCCCO DJYWKXYRGAMLRE-QXMHVHEDSA-N 0.000 description 1
- TVPWKOCQOFBNML-SEYXRHQNSA-N (z)-octadec-6-en-1-ol Chemical compound CCCCCCCCCCC\C=C/CCCCCO TVPWKOCQOFBNML-SEYXRHQNSA-N 0.000 description 1
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 description 1
- 229940100484 5-chloro-2-methyl-4-isothiazolin-3-one Drugs 0.000 description 1
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid 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
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- YSVBPNGJESBVRM-UHFFFAOYSA-L disodium;4-[(1-oxido-4-sulfonaphthalen-2-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(N=NC3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)O)=CC=C(S([O-])(=O)=O)C2=C1 YSVBPNGJESBVRM-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- ICFNGYKXNJGFLZ-UHFFFAOYSA-N octacosa-10,19-dien-1-ol Chemical compound CCCCCCCCC=CCCCCCCCC=CCCCCCCCCCO ICFNGYKXNJGFLZ-UHFFFAOYSA-N 0.000 description 1
- JEGNXMUWVCVSSQ-UHFFFAOYSA-N octadec-1-en-1-ol Chemical compound CCCCCCCCCCCCCCCCC=CO JEGNXMUWVCVSSQ-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-MDZDMXLPSA-N oleyl alcohol Chemical compound CCCCCCCC\C=C\CCCCCCCCO ALSTYHKOOCGGFT-MDZDMXLPSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/645—Mixtures of compounds all of which are cationic
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
- C11D3/0015—Softening compositions liquid
-
- 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
- C11D3/43—Solvents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels
-
- 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 invention relates to special active ingredients for the production of highly viscous washing and
- Cleaning formulations in particular fabric softeners, a process for their preparation and washing and cleaning formulations containing said active ingredients.
- the high viscosity of the products according to the invention can be achieved despite the low concentration of active substances and without the use of additional thickeners.
- washing and cleaning formulations in particular fabric softeners, are in demand, which have low active contents, i.e. low content of quaternary ammonium compounds, high viscosity.
- DE2928603 discloses so-called “hybrid” quats, among other things. These are characterized in that, in addition to alkanol and alkanol ester residues, they also have a long-chain alkyl residue.
- the hybrid quats of DE2928603 are said to give the laundry a pleasant soft feel. Viscosities of the fabric softener produced with these hybrid quats are not specified in DE 2928603. However, there is an indication that the viscosity of other substances and auxiliaries must be added to the fabric softener. Such addition of auxiliaries, in particular thickeners, is common in the prior art, but has ecological and economic disadvantages.
- WO 2016/055341 describes active substances comprising bis (2-hydroxypropyl) dimethylammonium methyl sulfate fatty acid esters with which aqueous and storage-stable
- Fabric softener formulations with high viscosity can be produced.
- a disadvantage of these active substances is that relatively large amounts have to be used to increase the viscosity.
- the object of the present invention was therefore to provide new active substances and new washing and cleaning formulations, in particular fabric softener formulations, which do not have the disadvantages of the prior art or only have them to a reduced extent.
- the washing and cleaning formulations should have a sufficiently high viscosity at the low active content required solely through the active substances according to the invention.
- the fabric softener products according to the invention are intended to have an at least comparable fabric softening effect to products of the prior art.
- Another object can be seen in providing washing and cleaning formulations, in particular fabric softener products, which are biodegradable.
- active substances are understood to mean compositions comprising mixtures of esterquats of the general formula I defined in more detail below. The activity of these esterquats is demonstrated, among other things, by their thickening effect, but also by their fabric softening effect.
- the active substances can consist exclusively of esterquats of the general formula I, but they can also, for example for better handling, be diluted with a solvent. "Washing and cleaning formulations" includes all types of washing and
- washing and cleaning formulations understood in which esterquats are commonly used. These are preferably fabric softener formulations.
- the washing and cleaning formulations according to the invention can contain the active substances according to the invention, but can also consist only of them. In addition to the active substances according to the invention, they usually also contain at least one perfume oil and water.
- high viscosity means a viscosity of more than 500 mPas, preferably more than 750 mPas, particularly preferably more than 1000 mPas.
- washing and cleaning formulation with “low active content” is understood to mean a washing and cleaning formulation which has a total active ingredient content of less than 5% by weight, particularly preferably less than 3% by weight, based on the overall composition of the washing and
- the active substances according to the invention contain mixtures of special ester quats of the general formula I defined in more detail below. Their use has resulted in fabric softener formulations which, despite their low active substance content, have a high viscosity.
- the viscosities were at least 10% above the maximum 500 mPas achieved in the prior art and ranged up to 2400 mPas. It was thus made possible solely by using the active substances according to the invention, the viscosity of the
- esterquats used according to the invention enable the production of ecologically advantageous washing and cleaning formulations.
- washing and cleaning formulations according to the invention can also be prepared without the addition of thickeners with a high viscosity and a low content of active substances. This increases the ecological, but also brings economic advantages. However, the fact that the washing and cleaning formulations according to the invention can be produced without the addition of thickeners does not fundamentally preclude their use.
- the present invention thus relates to active substances as claimed in claim 1 and to a process for their preparation as claimed in claim 6
- Cleaning formulation preferably fabric softener formulation, containing the active substances according to the invention as claimed in claim 7 and the use of
- the present invention relates in particular to active substances for the preparation of washing and cleaning formulations, preferably fabric softener formulations, which are characterized in that they are a mixture of several quaternary ammonium salts of the general formula I)
- R 1 is a linear or branched hydrocarbon radical with an iodine number less than or equal to 10, preferably less than or equal to 8, particularly preferably from 0 to 5, having 10 to 32 carbon atoms, preferably 12 to 22 carbon atoms, particularly preferably 14 to 20 carbon atoms and in particular 16 to 18 carbon atoms .
- R 2 , R 4 independently of one another, identical or different, selected from the group of double-bonded, preferably linear, hydrocarbon radicals having 1 to 4
- Carbon atoms preferably methylene, ethylene, and n-propylene, particularly preferably ethylene,
- R 3 is hydrogen or an acyl residue of a fatty acid with a chain length of 8 to 32
- Carbon atoms preferably 12 to 22 carbon atoms, in particular 14 to 18 carbon atoms,
- R 5 identical or different from R 3 , hydrogen or acyl radical of a fatty acid with a chain length of 8 to 32 carbon atoms, preferably 12 to 22 carbon atoms, in particular 14 to 18 carbon atoms,
- R 6 hydrocarbon radical having 1 to 4 carbon atoms, preferably methyl or ethyl, particularly preferably methyl,
- R 1 , R 2 and R 4 have the same meaning as in formula I, with one or more fatty acids corresponding to R 3 and R 5 , in a molar ratio of the sum of all the amines of the general formula II) to the sum of all the fatty acids of 0.8 to 1.5, preferably 0.8 to 1.4, particularly preferably 0.85 to 1.3, and very particularly preferably 0.9 to 1.2.
- Active substances according to the invention with significantly lower thickening ability.
- An excessively high molar ratio leads to the same effect, i.e. to a decrease in thickening ability.
- the inventors surprisingly found that the alkyl radical R 1 should have a high mobility, ie a small number of double bonds, preferably no double bonds. This is demonstrated in the examples when comparing R 1 tallow (see
- Comparative examples V3 to V6) with R 1 hydrogenated tallow shown.
- the proportion of double bonds in R 1 is expressed by the iodine number.
- the radicals R 1 used according to the invention have an iodine number of less than or equal to 10, preferably less than or equal to 8, particularly preferably from 0 to 5.
- R 1 is preferably a hydrocarbon radical which represents the hydrocarbon radical of fatty alcohols.
- a "hydrocarbon residue of fatty alcohol" in connection with the present earth invention is the remaining structure after deletion of the OH group of the fatty alcohol.
- a preferred radical R 1 is a hydrocarbon radical of an unbranched or branched monoalcohol with an alkyl group of 10 to 22 carbon atoms. Preferred radicals R 1 are
- Gadoleyl alcohol and mixtures thereof, in particular technical mixtures, preferably technical stearyl, palmityl or hydrogenated tallow fatty alcohols having 12 to 22, preferably 14 to 20 carbon atoms, and monounsaturated fatty alcohols such as oleyl alcohol, elaidyl alcohol, delta-9 cis-hexadecenol, delta-9-octadecenol, trans-delta-9-octadecenol, cis-delta-1 1-octadecenol, trans-10, cis-12-hexadecadien-1-ol, octacosa-10, 19-dien-1 -ol wherein hydrocarbon residues from mixtures of stearyl or hydrogenated tallow fatty alcohols with 14 to 22, particularly preferably 14 to 18 and very particularly preferably 16 to 18
- Carbon atoms are particularly preferred.
- the iodine number is the average iodine number of the mixture.
- the fatty acids described below ie the radicals R 3 and R 5 . Since the quats of the general formula I are obtained by reacting one or more amine (s) of the general formula II) defined above with one or more fatty acids corresponding to R 3 and R 5 , in the molar ratio defined above, it follows that some of the OH groups of the amine are retained as such. This is important to ensure the correct polarity of the quats.
- R 3 and R 5 can either be both acyl or both H or one of both acyl and one H. If the radicals R 3 and R 5 are both acyl radicals, they are preferably acyl esters of the same fatty acid or
- Preferred fatty acids for R 3 and R 5 are selected from
- Vegetable or tallow fatty acids preferably with an iodine number of 0 to 50, particularly preferably 5 to 45, very particularly preferably 10 to 25,
- Vegetable or tallow fatty acids with an iodine number less than or equal to 10, preferably less than or equal to 8, particularly preferably from 0 to 5,
- R 2 and R 4 are preferably identical and preferably both equal C2H4 or both equal C3H6, particularly preferably both equal C2H4.
- Particularly preferred active substances according to the invention are mixtures quaternary
- R 1 is a linear alkyl radical having 14 to 20, preferably 16 to 18 carbon atoms with an iodine number less than 8, preferably less than or equal to 5,
- R 2 , R 4 are equal to C2H4,
- R 3 , R 5 independently of one another, identical or different, identical to hydrogen or an acyl radical of a fatty acid with a chain length of 12 to 22 carbon atoms, preferably 16 to 18 carbon atoms,
- R 6 is methyl or ethyl, preferably methyl
- X methyl sulfate or ethyl sulfate, preferably methyl sulfate
- the active substances according to the invention result in the washing and cleaning formulations thus produced, preferably fabric softener formulations, having high viscosities even at low contents of these active substances and without additional thickeners.
- the washing and cleaning formulations according to the invention are preferred Fabric softener formulations thus contain the active substances according to the invention preferably in an amount of 1% by weight to 6% by weight, particularly preferably 2% by weight to 5% by weight, the weight percent based on the total composition.
- the washing and cleaning formulations can be preferred
- Fabric softener formulations water and other additive and / or auxiliary, e.g. selected from the group of emollients, pearlescent additives, dyes, insect repellents,
- Cleaning formulations may be included.
- the amounts of the respective additives depend on the intended use.
- Typical frame formulations for the respective applications are known in the art and are contained, for example, in the brochures of the manufacturers of the respective base and active ingredients. These existing formulations can usually be adopted unchanged. If necessary, the desired modifications can be made without complications by simple experiments for adaptation and optimization
- the active substances according to the invention are preferably produced by a process which comprises the following steps:
- step b) reaction of the amines from step a) with an alkylating agent selected from the group consisting of dimethyl sulfate and diethyl sulfate, for the preparation of quaternary ammonium salts of the formula (I).
- an alkylating agent selected from the group consisting of dimethyl sulfate and diethyl sulfate, for the preparation of quaternary ammonium salts of the formula (I).
- the active substance mixture obtained after step b) is preferably used for better handling in step
- Such solvents are, for example, ethanol, 1-propanol, 2-propanol, 1, 2- Ethylene glycol, 1, 2-propylene glycol, 1, 3-propylene glycol, dipropylene glycol, ethylene glycol ether or propylene glycol ether or mixtures thereof.
- the active substances according to the invention particularly preferably consist only of the mixture contained after step b) or of the dilute mixture obtained after step c).
- step b) or c) are preferred for the preparation of the washing and cleaning formulations according to the invention
- Fabric softener formulations preferably processed as follows:
- Water is placed in a stirred tank and heated to a temperature between 20 and 60 ° C.
- the active ingredients are melted and brought to a temperature between 30 and 60 ° C.
- the melt is introduced into the water reservoir with thorough stirring.
- the dispersion thus obtained is cooled and optionally further additives, described in more detail below, are added.
- the active substances according to the invention are used as active substances in washing and cleaning formulations. You can do this in principle in any washing and cleaning formulations. You can do this in principle in any washing and cleaning formulations.
- washing and cleaning formulations which have a high viscosity and very particularly preferably in those which are said to have a high viscosity with a low active content.
- washing and cleaning formulations are most preferably
- Preferred fabric softener formulations according to the invention for household, industrial and institutional applications, containing at least one of the active substances according to the invention are detergents, laundry care products, disinfectant laundry detergents, heavy duty laundry detergents, mild detergents, wool laundry detergents, fabric softeners and impregnating agents, detergents, laundry care agents, heavy duty detergents, mild detergents, wool detergents, fabric softeners, fabric softeners
- a fabric softener formulation according to the invention preferably contains the active substances according to the invention in an amount of 1% by weight to 5% by weight, preferably 2% by weight to 4% by weight, the% by weight based on the total formulation.
- the remaining 100% by weight preferably consists of water and / or at least one additive and / or auxiliary, selected from the group of emollients, viscosity regulators, pearlescent additives, dyes,
- compositions according to the invention can contain from 0.01 to 10% by weight, particularly preferably 0.1 to 5% by weight, based on the overall composition of the composition of one or more perfumes.
- compositions according to the invention can contain from 0.001 to 0.1% by weight, particularly preferably from 0.002 to 0.05% by weight, of one or more dyes.
- the fabric softener can contain a thickener known from the prior art, the thickeners known from WO 2007/125005
- Polyurethane thickeners are preferred. Examples of suitable thickeners are TEGO ® Visco Plus 3030 (manufacturer Evonik Tego Chemie), Acusol ® 880 and 882 (manufacturer Rohm & Haas),
- any defoamers known to be suitable for fabric softeners from the prior art can be used as defoamers.
- suitable commercially available defoamers are Dow Corning ® DB-1 10A and TEGO ® Antifoam ® 7001 XP.
- the compositions according to the invention can contain from 0.0001 to 0.05% by weight, preferably from 0.001 to 0.01% by weight, of one or more different defoamers.
- the fabric softener from the prior art can contain known bactericidal and / or fungicidal active substances, water-soluble active substances being preferred.
- suitable commercial bactericides are methylparaben, 2-bromo-2-nitro-1,3-propanediol, 2-methyl-4-isothiazolin-3-one and 5-chloro-2-methyl-4-isothiazolin-3-one.
- the aqueous fabric softener contain an oxidation inhibitor as a preservative.
- compositions according to the invention can contain from 0.0001 to 0.5, particularly preferably 0.001 to 0.2% by weight of one or more different preservatives.
- compositions according to the invention can contain from 0.001 to 0.1% by weight, preferably 0.001 to 0.01% by weight, of one or more different oxidation inhibitors.
- Typical frame formulations for the respective applications are known in the art and are contained, for example, in the brochures of the manufacturers of the respective base and active ingredients. These existing formulations can usually be adopted unchanged. If necessary, the desired modifications can be made without complications by simple experiments for adaptation and optimization.
- the iodine number indicates how many grams of halogen, calculated as iodine, from 100 g of an examined sample are bound under the conditions of a method.
- the measurement method according to Wijs according to DIN 53241-1: 1995-05 is used according to the invention.
- the iodine number of the radical R 1 on the amine of the general formula (II) can be measured directly
- the iodine number of the quaternary ammonium compound of the general formula (I) is measured by first saponifying acyl residues under alkaline conditions and the fatty acid and ammonium compound thus obtained according to known methods Separates methods.
- the iodine number of R 1 from which
- Ammonium compound, and that of the fatty acid can then be determined using the Wijs method.
- the viscosity is measured using a Brookfield LVT viscometer and a spindle suitable for the viscosity range at a temperature of 25 ° C and 30 rpm. 6.
- reaction water was caught in the outlet of the distillation bridge. After 2.5 hours, the vacuum was reduced to 20 mbar and the reaction continued for 1.5 hours.
- the condensation product thus obtained had an acid number of 0.9 mg KOH / g and an amine number of 96.2 mg KOH / g.
- the reaction mixture was cooled to 80 ° C. 186.2 g (1, 477 mol) of dimethyl sulfate were added dropwise with stirring in the course of one hour, the temperature being kept in a range from 80 ° -95 ° C. Then 120 g of anhydrous ethanol were added and the mixture was stirred at 80 ° C. for one hour.
- the quat mixture thus obtained had an amine number of 3.1 mg KOH / g.
- Table 4 shows various washing and cleaning formulations according to the invention as examples.
- Quat mixtures were prepared and mixed with water, so that each formulation of 3% by weight Quat mixture (calculated on the solids content), 0.2% Perfume oil, and water ad 100% resulted.
- the viscosity was determined in each case from the formulation obtained.
- V3 with B7, V4 with B6, V5 with B7 and V6 with B2 show that the use of residues R 1 with an iodine number less than 10 instead of a residue R 1 with a high iodine number under otherwise identical conditions leads to significantly higher viscosities leads.
- the comparison of V7 with B1 to B3 shows the influence of the molar ratio of fatty acid to amine. If this is too low, as in V7, a sufficient thickening effect is not achieved.
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
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- Organic Chemistry (AREA)
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Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP18181831 | 2018-07-05 | ||
PCT/EP2019/067540 WO2020007775A1 (de) | 2018-07-05 | 2019-07-01 | Aktivstoffe für hochviskose wasch- und reinigungsformulierungen |
Publications (2)
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EP3818137A1 true EP3818137A1 (de) | 2021-05-12 |
EP3818137B1 EP3818137B1 (de) | 2022-11-09 |
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EP19734091.2A Active EP3818137B1 (de) | 2018-07-05 | 2019-07-01 | Aktivstoffe für hochviskose wasch- und reinigungsformulierungen |
Country Status (6)
Country | Link |
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US (1) | US11692153B2 (de) |
EP (1) | EP3818137B1 (de) |
CN (1) | CN112368362B (de) |
BR (1) | BR112020026982A2 (de) |
ES (1) | ES2936215T3 (de) |
WO (1) | WO2020007775A1 (de) |
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EP3679117A1 (de) | 2017-09-06 | 2020-07-15 | Evonik Operations GmbH | Mikroemulsion mit quaternärer ammoniumverbindung, insbesondere zur herstellung von weichspülerformulierungen |
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-
2019
- 2019-07-01 US US17/257,661 patent/US11692153B2/en active Active
- 2019-07-01 CN CN201980045191.4A patent/CN112368362B/zh active Active
- 2019-07-01 WO PCT/EP2019/067540 patent/WO2020007775A1/de active Application Filing
- 2019-07-01 EP EP19734091.2A patent/EP3818137B1/de active Active
- 2019-07-01 BR BR112020026982-4A patent/BR112020026982A2/pt unknown
- 2019-07-01 ES ES19734091T patent/ES2936215T3/es active Active
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BR112020026982A2 (pt) | 2021-03-30 |
ES2936215T3 (es) | 2023-03-15 |
US11692153B2 (en) | 2023-07-04 |
EP3818137B1 (de) | 2022-11-09 |
US20210277329A1 (en) | 2021-09-09 |
WO2020007775A1 (de) | 2020-01-09 |
CN112368362B (zh) | 2022-05-24 |
CN112368362A (zh) | 2021-02-12 |
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