EP1806392B1 - Stable aqueous esterquat compositions - Google Patents
Stable aqueous esterquat compositions Download PDFInfo
- Publication number
- EP1806392B1 EP1806392B1 EP20060013688 EP06013688A EP1806392B1 EP 1806392 B1 EP1806392 B1 EP 1806392B1 EP 20060013688 EP20060013688 EP 20060013688 EP 06013688 A EP06013688 A EP 06013688A EP 1806392 B1 EP1806392 B1 EP 1806392B1
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- EP
- European Patent Office
- Prior art keywords
- composition
- formula
- weight
- metal salt
- esterquat
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 47
- 150000003839 salts Chemical class 0.000 claims description 26
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 150000005690 diesters Chemical class 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 claims description 9
- 150000005691 triesters Chemical class 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- -1 alkaline earth metal salt Chemical class 0.000 claims description 8
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000011592 zinc chloride Substances 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000002304 perfume Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910000329 aluminium sulfate Inorganic materials 0.000 claims description 3
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 3
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 3
- 239000011686 zinc sulphate Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 claims description 2
- 239000003792 electrolyte Substances 0.000 claims description 2
- 239000003752 hydrotrope Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003605 opacifier Substances 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 150000004665 fatty acids Chemical class 0.000 description 11
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 11
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 3
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 235000013830 Eruca Nutrition 0.000 description 1
- 241000801434 Eruca Species 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 159000000013 aluminium salts Chemical class 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 239000002738 chelating agent Chemical class 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 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
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C11D3/0005—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
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/046—Salts
Definitions
- Quaternized fatty acid triethanolamine (TEA) esters and quaternized fatty acid methyldiethanolamine (MDEA) esters which are commonly called “esterquats", are widely known in detergent industry. They provide a softening effect to textile materials, especially for cotton. These compounds are made by esterification of triethanolamine (TEA) or methyldiethanolamine (MDEA) with a fatty acid and subsequent quaternisation by reacting with a short chain alkyl sulfate or alkyl chloride.
- esterification of TEA esterquats one, two or three hydroxyl groups may react with the fatty acid and accordingly commercially available esterquat compositions contain quaternized mono-, di- and tri-esterquats. For the case of MDEA esterquats, only mono and di-esterquats are present.
- a problem of aqueous compositions containing these Esterquats is that the Esterquats are not stable over prolonged storage since they undergo hydrolysis. In order to prevent hydrolysis it is known to add alkali metal salts ( JP 10-251 972 ).
- the invention accordingly provides aqueous compositions consisting of an esterquat or mixtures thereof of the formula I wherein R is C 1 -C 4 -alkyl, preferably methyl, X has the same meaning as R or X is a group of the formula -C 2 H 4 OR 2 , R 1 and R 2 are independently hydrogen or a group -COR 3 , R 3 is C 7 -C 21 -alkyl or C 7 -C 21 -alkenyl and A is an anion, preferably chloride or methosulfate, and a metal salt, and optionally one or more auxiliary as defined in claim 1, which composition is free of alkali or alkaline earth metal salt, phthalocyanine metal complexes or phthalocyanine metal salts.
- X in the formula (I) may be either an alkyl group R or a further hydroxyethyl group which may be esterified
- the claimed compositions contain either TEA esterquats or MDEA esterquats of the following formulas II and III:
- the group -COR 3 is preferably derived from natural occurring fatty acids such as capronic acid, caprylic acid, caprinic acid, lauric acid, myristiric acid, palmic acid, isostearic acid, stearic, oleic acid, eluidinic acid, arachinic acid, behenic acid and eruca acid.
- Preferred acids containing the group -COR 3 are C 12 /C 18 coco fatty acids, tallow fatty acid, fully or partially hydrogenated tallow fatty acid, palm fatty acid, partially or fully hydrogenated palm fatty acid or stearic acid.
- ester quats of formula II are present in the form of mixtures of the mono-, di- or triester of triethanolamine.
- Preferred mixtures are those which have 10 to 38 % by weight of the monoester (R 1 and R 2 being hydrogen), 46 to 63 % by weight of the diester (R 1 being hydrogen and R 2 -COR 3 ) and 7 to 25 % by weight of the triester (R 1 and R 2 being -COR 3 ).
- Especially preferred are also the following mixtures (all percentages are by weight):
- esterquats of formula III are present in the form of mixtures of mono and di-ester of methyldiethanolamine.
- Preferred mixtures are those which have from 1 to 70% by weight of monoester (R 1 being hydrogen), and from 30 to 99% by weight of the diester (R 1 being -COR 3 ).
- Particular preferred are also the following mixtures (all percentages by weight): Monoester 2-60%; diester 35-98%, Monoester 2-40%; diester 60-98%.
- the ester quat compositions accordingly to the present invention contain in general 0.5 to 30, preferable 2 to 24 and especially 4 to 22 % by weight of the ester quats of the formula II.
- a salt is added which is not an alkali or alkaline earth metal salt.
- the claimed compositions are free of such salts.
- Preferred salts are transition metal salts, more preferably are zinc and aluminium salts such as ZnSO 4 , ZnCl 2 AlCl 3 or Al 2 (SO 4 ) 3 . These salts are present in an amount preferably from 0.002 to 10.0, preferably 0.03 to 5.0, and preferably 0.04 to 3.0 % by weight.
- compositions according to the invention are also free of rare earth metal salts, metal salts of fatty acids or chelating agents.
- compositions according to the present invention can be made by mixing the aqueous solution of the ester quats of formulas II and III final softener formulations with the salt.
- the salt can be added at any moment during the softeners process preparation and either in solid form or an aqueous solution. Heating and stirring is recommended for making the claimed compositions.
- a concentrated pre-mix containing the same molar and/or mass ratio between the ester quats and the additives can be prepared in order to be diluted up to 45 times.
- Other ingredients such as solvent, water or any ingredient that could be part of the final formulation may be added.
- compositions according to the invention comprise, in addition to the mentioned compounds additives and auxiliaries which are customary and specific in each case selected from electrolytes, perfumes, perfume carriers, colorants, hydrotropes, antifoaming agents, other thickening agents, opacifiers, preservatives, , anti corrosion agents, co-surfactants and solvents.
- additives and auxiliaries which are customary and specific in each case selected from electrolytes, perfumes, perfume carriers, colorants, hydrotropes, antifoaming agents, other thickening agents, opacifiers, preservatives, , anti corrosion agents, co-surfactants and solvents.
- the composition may be composed only of water, one or more esterquat of formula (I) and a metal salt, which composition is free of an alkali or alkali earth metal salt or phthalocyanine metal salts.
- the metal salt preferably is ZnSO 4 , ZnCl 2 , AlCl 3 or Al 2 (SO 4 ) 3 .
- compositions according to the invention are notable for a good storage stability and can be used as such as fabric softener or can be further diluted with water either at around room temperature or under heating .
- ester quat used in all examples was a mixture of the following compounds:
- ester quat ZnCl 2 crossing point (days) 1 5 % active matter - 53 2 5 % active matter 0.13 63 3 5% active matter 0.61 79 ester quat AlCl 3 crossing point (days) 4 5 % active matter 0.08 65 5 5 % active matter 0.40 69
- compositions based on MDEA esterquats (formula III):
- the stability profile of the formulations was monitored through storage at 45°C.
- the hydrolysis stability profile was analysed according to the amount of mono, di and triester analysed time to time.
- MDEA esterquats it was analysed only the amount of mono and diesterquats.
- As hydrolysis happens the amount of monoester increases while the amount of diester decreases for both, TEA and MDEA estequarts.
- TEA esterquats there is also a decrease on the triester amount.
- the amount of monoester is higher than the amount of diester for TEA and MDEA esterquats and for TEA esterquats the triester is presented in low levels.
- the crossing point of the di and monoester curves was defined as the reference for comparison between the formulations. The later the crossing point, the lower the hydrolysis rate and, consequently, the more stable the formulation.
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
- Quaternized fatty acid triethanolamine (TEA) esters and quaternized fatty acid methyldiethanolamine (MDEA) esters, which are commonly called "esterquats", are widely known in detergent industry. They provide a softening effect to textile materials, especially for cotton. These compounds are made by esterification of triethanolamine (TEA) or methyldiethanolamine (MDEA) with a fatty acid and subsequent quaternisation by reacting with a short chain alkyl sulfate or alkyl chloride. In the step of esterification of TEA esterquats, one, two or three hydroxyl groups may react with the fatty acid and accordingly commercially available esterquat compositions contain quaternized mono-, di- and tri-esterquats. For the case of MDEA esterquats, only mono and di-esterquats are present.
- A problem of aqueous compositions containing these Esterquats is that the Esterquats are not stable over prolonged storage since they undergo hydrolysis. In order to prevent hydrolysis it is known to add alkali metal salts (
JP 10-251 972 - It has now been found that also other metal salts are capable of preventing hydrolysis of esterquats.
- The invention accordingly provides aqueous compositions consisting of an esterquat or mixtures thereof of the formula I
-
- The group -COR3 is preferably derived from natural occurring fatty acids such as capronic acid, caprylic acid, caprinic acid, lauric acid, myristiric acid, palmic acid, isostearic acid, stearic, oleic acid, eluidinic acid, arachinic acid, behenic acid and eruca acid. Preferred acids containing the group -COR3 are C12/C18 coco fatty acids, tallow fatty acid, fully or partially hydrogenated tallow fatty acid, palm fatty acid, partially or fully hydrogenated palm fatty acid or stearic acid.
- As mentioned above the ester quats of formula II are present in the form of mixtures of the mono-, di- or triester of triethanolamine. Preferred mixtures are those which have 10 to 38 % by weight of the monoester (R1 and R2 being hydrogen), 46 to 63 % by weight of the diester (R1 being hydrogen and R2 -COR3) and 7 to 25 % by weight of the triester (R1 and R2 being -COR3). Especially preferred are also the following mixtures (all percentages are by weight):
- Monoester: 18 - 22 %; diester 58 - 62 %; triester 18 - 22 %.
- Monoester: 20 - 27 %; diester 53 - 60 %; triester 16 - 23 %.
- Monoester: 29 - 37 %; diester 46 - 57; triester 7 - 14 %.
- In the same way, the esterquats of formula III are present in the form of mixtures of mono and di-ester of methyldiethanolamine. Preferred mixtures are those which have from 1 to 70% by weight of monoester (R1 being hydrogen), and from 30 to 99% by weight of the diester (R1 being -COR3). Especially preferred are also the following mixtures (all percentages by weight): Monoester 2-60%; diester 35-98%, Monoester 2-40%; diester 60-98%.
- The ester quat compositions accordingly to the present invention contain in general 0.5 to 30, preferable 2 to 24 and especially 4 to 22 % by weight of the ester quats of the formula II. In order to enhance the stability of these aqueous compositions a salt is added which is not an alkali or alkaline earth metal salt. The claimed compositions are free of such salts. Preferred salts are transition metal salts, more preferably are zinc and aluminium salts such as ZnSO4, ZnCl2 AlCl3 or Al2(SO4)3. These salts are present in an amount preferably from 0.002 to 10.0, preferably 0.03 to 5.0, and preferably 0.04 to 3.0 % by weight.
- In a preferred aspect the compositions according to the invention are also free of rare earth metal salts, metal salts of fatty acids or chelating agents.
- The compositions according to the present invention can be made by mixing the aqueous solution of the ester quats of formulas II and III final softener formulations with the salt. The salt can be added at any moment during the softeners process preparation and either in solid form or an aqueous solution. Heating and stirring is recommended for making the claimed compositions.
In order to make easier the preparation of the disclosed invention, a concentrated pre-mix containing the same molar and/or mass ratio between the ester quats and the additives can be prepared in order to be diluted up to 45 times. Other ingredients such as solvent, water or any ingredient that could be part of the final formulation may be added. - Depending on the intended use, the compositions according to the invention comprise, in addition to the mentioned compounds additives and auxiliaries which are customary and specific in each case selected from electrolytes, perfumes, perfume carriers, colorants, hydrotropes, antifoaming agents, other thickening agents, opacifiers, preservatives, , anti corrosion agents, co-surfactants and solvents.
- In a second aspect of the invention the composition may be composed only of water, one or more esterquat of formula (I) and a metal salt, which composition is free of an alkali or alkali earth metal salt or phthalocyanine metal salts. The metal salt preferably is ZnSO4, ZnCl2, AlCl3 or Al2(SO4)3.
- The compositions according to the invention are notable for a good storage stability and can be used as such as fabric softener or can be further diluted with water either at around room temperature or under heating .
- All the following compositions based on formula (II) have been prepared in the following way:
- I
- Water was heated to 85°C
- II
- addition of a varying amount of a 50 % solution of the salt as indicated and stirring for approximately 5 minutes with approximately 150 rpm
- III
- addition of the ester quat (5 % active content referred to the final composition)
- IV
- cooling under stirring within 30 minutes.
- The ester quat used in all examples was a mixture of the following compounds:
- 16 - 24 % of a compound of the formula
- 58 - 64 % of a compound of the formula
- 16- 24 % of a compound of the formula
- For compositions based on TEA esterquats (formula II):
ester quat ZnCl2 crossing point (days) 1 5 % active matter - 53 2 5 % active matter 0.13 63 3 5% active matter 0.61 79 ester quat AlCl3 crossing point (days) 4 5 % active matter 0.08 65 5 5 % active matter 0.40 69 - For compositions based on MDEA esterquats (formula III):
- I.
- Water was heated to 45°C
- II.
- Addition of the esterquat at 50°C
- III.
- Cooling under stirring with approximately 150 rpm for 20 minutes
- IV.
- Fast cooling under stirring for 10 minutes
- V.
- Addition of a varying amount of a 50 % solution of the salt as indicated and stirring for approximately 5 minutes with approximately 150 rpm
- The stability profile of the formulations was monitored through storage at 45°C. The hydrolysis stability profile was analysed according to the amount of mono, di and triester analysed time to time. In the case of MDEA esterquats, it was analysed only the amount of mono and diesterquats. As hydrolysis happens the amount of monoester increases while the amount of diester decreases for both, TEA and MDEA estequarts. However, for TEA esterquats there is also a decrease on the triester amount. After a certain time the amount of monoester is higher than the amount of diester for TEA and MDEA esterquats and for TEA esterquats the triester is presented in low levels. The crossing point of the di and monoester curves was defined as the reference for comparison between the formulations. The later the crossing point, the lower the hydrolysis rate and, consequently, the more stable the formulation.
- The results given above show that the addition of ZnCl2 or AlCl3 shifts the crossing point further as compared with the same formulation containing no salt. This indicates the positive effect on hydrolysis stability of these salts.
ester quat | ZnCl2 | crossing point (days) | |
1 | 2% active matter | - | 28 |
2 | 2% active matter | 0.32 | 38 |
Claims (11)
- Aqueous compositions consisting of an esterquat or mixtures thereof of the formula 1
- A composition as claimed in claim 2 wherein the ester quat is of the formula II and is composed of 10 - 38 % by weight of monoester, 46 - 63 % by weight of diester and 7 - 25 % by weight of triester.
- A composition as claimed in claim 3 wherein the ester quat is of the formula III and is composed from 1-70% by weight of the monoester and from 30-99% by weight of diester.
- A composition as claimed in claim 1 wherein the total amount of ester quat of the formula II or of the formula III is from 0.5 to 30 % by weight.
- A composition as claimed in claim 1 containing ZnCl2, AlCl3, ZnSO4 or Al2(SO4)3 as metal salt.
- A composition as claimed in claim 1 containing 0.002 to 10 % by weight of the metal salt.
- A composition as claimed in claim 1 containing one or more additives or auxiliaries.
- A composition consisting of water, one or more esterquat of the formula I as defined in claim 1 and a metal salt, which composition is free of alkali or alkali earth metal salt or phthalocyanine metal salts.
- A composition as claimed in claim 1 which is a concentrated pre-mix of the esterquat and metal salt.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP20060013688 EP1806392B1 (en) | 2005-09-06 | 2006-07-01 | Stable aqueous esterquat compositions |
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EP05019277 | 2005-09-06 | ||
EP20060013688 EP1806392B1 (en) | 2005-09-06 | 2006-07-01 | Stable aqueous esterquat compositions |
Publications (2)
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EP1806392A1 EP1806392A1 (en) | 2007-07-11 |
EP1806392B1 true EP1806392B1 (en) | 2008-12-24 |
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EP20060013688 Not-in-force EP1806392B1 (en) | 2005-09-06 | 2006-07-01 | Stable aqueous esterquat compositions |
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EP (1) | EP1806392B1 (en) |
DE (1) | DE602006004426D1 (en) |
ES (1) | ES2317370T3 (en) |
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ES2627705T3 (en) | 2010-04-28 | 2017-07-31 | Evonik Degussa Gmbh | Textile softening composition |
GB201018916D0 (en) | 2010-11-09 | 2010-12-22 | Champion Technologies Ltd | Corrosion inhibition |
WO2013113453A1 (en) * | 2012-01-30 | 2013-08-08 | Evonik Industries Ag | Fabric softener active composition |
JP5992605B2 (en) | 2012-05-07 | 2016-09-14 | エボニック デグサ ゲーエムベーハーEvonik Degussa GmbH | Fabric softener active composition and process for producing the same |
BR102014025172B1 (en) | 2013-11-05 | 2020-03-03 | Evonik Degussa Gmbh | METHOD FOR MANUFACTURING A TRIS- (2-HYDROXYETHYL) -METHYLMETHYL ESTER OF FATTY ACID AND ACTIVE COMPOSITION OF SOFTENING CLOTHES |
UA119182C2 (en) | 2014-10-08 | 2019-05-10 | Евонік Дегусса Гмбх | Fabric softener active composition |
EP3208314B1 (en) | 2016-02-16 | 2018-08-15 | Omya International AG | Process for manufacturing white pigment containing products |
EP3208315A1 (en) | 2016-02-16 | 2017-08-23 | Omya International AG | Process for manufacturing white pigment containing products |
CN109208328B (en) * | 2017-07-07 | 2021-10-22 | 广州蓝月亮实业有限公司 | Aqueous fabric softening composition |
EP3444036A1 (en) | 2017-08-16 | 2019-02-20 | Omya International AG | Indirect flotation process for manufacturing white pigment containing products |
CN112384601B (en) | 2018-07-11 | 2022-06-17 | 科莱恩国际有限公司 | Preparation and use of high quality esterquat derived from rice bran fatty acids |
WO2022148673A1 (en) | 2021-01-11 | 2022-07-14 | Clariant International Ltd | Hydrogenated esterquats from rice bran fatty acids and their preparation |
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JPH10251972A (en) | 1997-03-11 | 1998-09-22 | Lion Corp | Hydrolysis inhibitor for cationic surfactant and cationic surfactant composition |
NZ331196A (en) * | 1997-08-15 | 2000-01-28 | Ciba Sc Holding Ag | Water soluble fabric softener compositions comprising phthalocyanine, a quaternary ammonium compound and a photobleaching agent |
DE19756679A1 (en) * | 1997-12-19 | 1999-07-01 | Henkel Ecolab Gmbh & Co Ohg | Textile treatment agent for the hydrophobization of textile surfaces |
DE19904513A1 (en) * | 1999-02-04 | 2000-08-10 | Cognis Deutschland Gmbh | Detergent mixtures |
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- 2006-07-01 DE DE200660004426 patent/DE602006004426D1/en active Active
- 2006-07-01 ES ES06013688T patent/ES2317370T3/en active Active
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EP1806392A1 (en) | 2007-07-11 |
DE602006004426D1 (en) | 2009-02-05 |
ES2317370T3 (en) | 2009-04-16 |
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