EP4520812A1 - Formulations adoucissantes comprenant des melanges de tensioactifs cationiques - Google Patents
Formulations adoucissantes comprenant des melanges de tensioactifs cationiques Download PDFInfo
- Publication number
- EP4520812A1 EP4520812A1 EP23382901.9A EP23382901A EP4520812A1 EP 4520812 A1 EP4520812 A1 EP 4520812A1 EP 23382901 A EP23382901 A EP 23382901A EP 4520812 A1 EP4520812 A1 EP 4520812A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- mixture
- water
- group
- softener
- acid
- 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.)
- Withdrawn
Links
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
Definitions
- the present invention relates to mixtures of cationic surfactants.
- the invention also relates to softener compositions prepared by directly dispersing, at cold temperatures, the mixtures of cationic surfactants in water, wherein such softener compositions are stable upon storage.
- Quaternary ester ammonium compounds commonly referred to as “esterquats” (EQ) have found broad use as fabric softener actives due to their high softening performance (e.g., for softening textile fibers and fabrics as well as keratinous fibers, such as hair), their biodegradability, reasonably low aquatic toxicity, and good cosmetic compatibility.
- Softener formulations comprising esterquats need specific manufacture procedures (including stirring and temperature conditions) to ensure stability and avoid phase separation in the aqueous dispersion.
- manufacture procedures including stirring and temperature conditions
- softener active formulations which in combination with perfume, show a clear viscous liquid that can be directly, and easily dispersed in water, at temperatures from 5°C to 40°C, including tap water, wherein such formulations are homogeneous and stable upon storage.
- Another requirement for the softener formulations is the reduction of their environmental footprint from manufacturing to their use as softening ingredients, thus, obtaining more sustainable products that can contribute to various advantageous effects, such as water reduction, plastic reduction, energy reduction and/or ecological acceptability of the products and their use.
- the possibility to disperse, with cold temperatures, from 5°C to 40°C, the softening agent in water that is not sensitive to water hardness, that is, water that does not need to be deionized makes possible to lessen the necessity of resources to treat the water for softening agent producers, as well as it makes it possible for the final consumer to directly prepare a fabric softener at home, from concentrated softener agents, directly dispersing the softening agent in the tap water which is easily available at households.
- WO2016096614A1 describes a fabric treatment agent comprising specific esterquats.
- the fabric softener formulation with high storage stability is provided only in the additional presence of cationic thickeners and non-ionic emulsifiers.
- EP1136471A1 describes cationic surfactants obtained from alkanolamines, dicarboxylic acids and fatty alcohols. Patent describes that such cationic surfactant show efficacy in softening and conditioning natural and synthetic fibres.
- the present invention aims at the problem of providing esterquat-based softener compositions capable to be easily and fast dispersed in water, providing homogeneous and stable dispersions, not sensitive to water hardness, as well as being easily prepared at room temperature and stable upon storage.
- the present invention provides a mixture of cationic surfactants that is obtainable from a process comprising the steps: Step I: esterification of a) with b), and Step II: cation formation from the reaction products of Step I, wherein:
- the present invention further provides a softener composition.
- the softener composition can be a diluted softener composition or a concentrated softener composition comprising such mixture.
- the compositions can be used to softening fabrics or fibres, e.g., by comprising mixing, particularly dispersing, the composition with water, preferably with tap water, or by introducing the concentrated composition directly into a washing machine.
- the present invention further provides the use of the softener composition(s) for softening fabrics and/or keratin-based-fibres.
- This aspect can alternatively be formulated as a method for softening fabrics and/or keratin-based fibers, the method comprising contacting the fibers with the softener composition of the invention; or, alternatively, the method comprising: mixing the composition of the invention with water; and then contacting the resulting softening composition to textiles or fabrics.
- any ranges given include both the lower and the upper end-points of the range.
- the present inventors have surprisingly found that particular mixtures of cationic surfactants (esterquats (EQ)) obtainable by reacting a combination of mono- and di-carboxylic acids with alkanoamine(s), and subsequent cation formation, can give in combination with perfume, clear and stable viscous liquids, that are capable of providing softening effect, that can be easily dispersed into water, including tap water, thus providing homogenous and stable dispersions, not sensitive to water hardness, as well as being easily prepared at room temperatures and stable upon storage. These effects can be observed even in the absence of further additives.
- EQ cationic surfactants
- the mixture comprising cationic surfactants is obtainable by a process comprising the steps: Step I: esterification of a) with b), and Step II: cation formation from the reaction products of Step I, wherein:
- the process followed to obtain the mixture of the invention is performed in the absence of any polyol.
- a polyol it is understood any alcohol compound containing two or more hydroxyl groups.
- the process followed to obtain the mixture of the invention is perfomed in the absence of trimethylolpropane (TMP), glycerine and neopentyl glycol.
- TMP trimethylolpropane
- Saponification value is the number of miligrams (mg) of potassium hydroxide which is required to saponify 1 g of product. It can be determined according to method ISO 3657.
- the saponification value of the mixture of cationic surfactants is from 140 to 205, preferably from 150 to 190, more preferably from 150 to 180 mg of KOH/ g of mixture of cationic surfactant, wherein saponification value is determined according to ISO 3657.
- the saponification value of the mixture of the invention is from 150 to 180 mg KOH/g, and the molar ratio of monoacid/diacid (b1/b2) is from 3.0 to 4.0.
- the alkanolamine(s) of formula (I) is/are selected from triethanolamine, N-methyldiethanolamine, N-methyldiisopropanolamine and triisopropanolamine, each of which is optionally alkoxylated with ethylene oxide or propylene oxide, and mixtures thereof.
- each L is selected from ethane-1,2-diyl, 1-hydroxyethane-1,2-diyl, cis-ethene-1,2-diyl, trans-ethene-1,2-diyl, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, cyclohexane-1,4-diyl, octane-1,8-diyl and 1,4-phenylenyl; preferably butane-1,4-diyl, hexane-1,6-diyl or octane-1,8-diyl.
- the dicarboxylic acid of formula (III) is selected from succinic, malic, glutaric, adipic, sebacic, pimelic, suberic, maleic and terephthalic acid, acids obtained by thermal oligomerisation of unsaturated fatty acids, and mixtures thereof.
- the reactive derivative(s) of the dicarboxylic acid(s) of the general formula (III) are one or more selected from halide, anhydride, preferably mixed anhydride with acetic acid or cyclic anhydride.
- the monocarboxylic acid(s) of formula (II) are synthetic fatty acids and/or are obtained from fats or oils of natural origin, and are optionally hydrogenated; or are derived from oils of vegetal origin which are optionally hydrogenated.
- the monocarboxylic acid(s) of formula (II) are selected from those which are obtained from tallow, palm, olive, coconut, sunflower, soya, rapeseed, grape marc and grape, each of which can be hydrogenated, partially hydrogenated, or non-hydrogenated.
- the carboxylic monoacid(s) of formula (II) is one or more selected from caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, eleostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid, and mixtures thereof which are obtained for example by pressure splitting of natural fats and oils, in the reduction of aldehydes from Roelen's oxosynthesis or dimerization of unsaturated fatty acids, stearic acids, isostearic acid, palmitic acid, myristic acid, lauric acid, capric acid, caprylic acid, 2-e
- the iodine value of the carboxylic monoacid(s) of formula (II) is from 0 to 150, preferably from 30 to 100, more preferably from 65 to 85.
- the molar ratio of monoacid/diacid (b1/b2) in the mixture of cationic surfactants is from 3.0 to 4.0, the saponification value is from 150 to 180 mg KOH/g, and the iodine value of the monocarboxylic acid is from 65 to 85.
- the compounds corresponding to a.1 can be from natural origin or from synthetic origin.
- Step I is an esterification step of reacting a) with b).
- monoacid b.1 and diacid b.2 are combined with alkanolamine a.1.
- the obtained mixture is heated.
- the mixture is heated to reflux under atmospheric pressure, e.g., for 1-5, preferably 2-4 hours at 140-200 °C, preferably 160-180°C.
- step I is performed until no more water is distilled off the reaction mixture.
- step II The reaction product obtained from step I is subjected to cation formation in step II.
- an organic solvent is added before step II.
- the organic solvent does not play an active role in a chemical reaction, but it is added for the purpose of facilitating the reaction taking place in step II.
- Step II can correspond to the formation of the addition salts of the alkanolamine esters obtained from Step I with mineral or organic acids, preferably wherein the mineral or organic acids are one or more selected from hydrochloric, sulphuric, phosphoric, citric and lactic acid.
- step II can correspond to the quaternisation of reaction mixtures of Step I with alkylating agent(s), preferably wherein the alkylating agents are one or more selected from methyl chloride, methyl bromide, dimethyl sulphate, diethyl sulphate and dimethyl carbonate.
- Step II can be performed at room temperature or elevated temperature, e.g., 40-100 °C, preferably 50-90 °C; preferably for 1-5 hours, more preferably 2-4 hours, or until the virtually complete absence of amine value was verified by acid/base assay.
- the mixture further comprises an organic solvent, preferably an alcohol, more preferably ethanol, n-propanol or isopropanol, butanols, glycol, propane or butanediol, glycerol, diglycol, propyl or butyl diglycol, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, propylene glycol methyl, ethyl or propyl ether, dipropylene glycol methyl or ethyl ether, methoxy, ethoxy or butoxy triglycol, 1-butoxyethoxy-2-propanol, 3-methyl-3-methoxybutanol, or propylene glycol t-butyl ether.
- the organic solvent is ethanol, n-propanol or isoprop
- organic solvents used to facilitate step II are not recognized as polyols as defined in step I.
- the content of the organic solvent in the cationic surfactant mixture is 0-30%, preferably 0-20%, more preferably 10-20% by weight.
- the mixture is essentially water-free.
- the mixture essentially consists of the reaction products of steps I and II, and optionally an organic solvent.
- the mixture consists of the reaction products of steps I and II and solvent, if any, and unreacted starting materials as well as inevitable impurities from the production process, if any.
- the mixture of the invention due to the process followed, based on the esterification of monocarboxylic acids and dicarboxylic acid with alkanolamines, comprises one or more quaternary ester ammonium compounds of formula (IV): Wherein
- the quaternary ester ammonium compound of the invention is an ethoxylated and/or propoxylated esterquat.
- the order of sequence of the ethylene oxide and the propylene oxide group is not critical for the invention.
- the quaternary ammonium compound is preferably non-ethoxylated, non-propoxylated.
- n, r, and p are equal to 2. In another preferred embodiment m and p are equal to 2 and r is equal to 1.
- q represents a number within the range of 0 to 10, more preferably within the range of 0 to 6, most preferred 0.
- A preferably represents an halide, phosphate or alkylsulphate, more preferably an alkylsulphate, most preferred methylsulphate.
- the mixture of the invention comprises at least one or more quaternary mono-ester ammonium compound of formula (IV.1), at least one or more quaternary di-ester ammonium compound of formula (IV.2) and/or at least one quaternary tri-ester ammonium compound of formula (IV.3) wherein R8 and R9 each independently represents -H, or -OH; and X1, R7, T, a, b, q, m, r, p and A are as hereinabove described.
- the mixture comprises or consists of at least one or more quaternary mono-, di- or tri-ester ammonium compounds represented by formula (IV.1), (IV.2), (IV.3), as defined above, wherein R8 and R9 independently represent -OH; each m, r, p represents number 2, and X1, R7, T, a, b, q, m, r, p and A have the meanings as indicated above for formula (IV.1), (IV.2), (IV.3).
- R7 is a linear or branched alkyl containing 5 to 23 carbon atoms or a linear alkenyl group containing 5 to 23 carbon atoms and from 1 to 3 double bonds; preferably, the alkyl or alkenyl group contains from 11 to 21 carbon atoms.
- the mixture comprises at least a quaternary mono-ester ammonium compound, at least a quaternary di-ester ammonium compound, and at least a quaternary tri-ester ammonium compound, wherein the total content of quaternary ester ammonium compound is from 30 to 90% wt., preferably from 40 to 70% wt., based on the total weight of mixture of cationic surfactant.
- the content of quaternary ester ammonium is determined by HPLC using a C18 reverse phase column and an evaporative light scattering detector (ELSD).
- the iodine value of the mixture of cationic surfactants obtainable by the hereinabove described process is from 0 to 100, preferably from 20 to 80, more preferably from 30 to 50.
- a softener composition preferably a fabric-softening and/or keratin-based-fibres-softening composition, comprising the mixture of cationic surfactants according to the invention.
- These softener compositions can be diluted softener compositions, wherein water content is higher than 50& wt., preferably higher than 80% wt., more preferably higher than 85% wt., based on the total weight of the fabric softener and/or the compositions can be concentrated softener compositions, wherein water content is lower than 50% wt., preferably lower than 30% wt., more preferably lower than 10% wt., even more preferably lower than 5% wt., most preferably lower than 1% wt., based on the total weight of the fabric softener.
- Such concentrated compositions can be directly added to the washing machine and/or can be added in a soluble pouch and/or are suitable for being dispersed in cold water by consumer at home.
- the softener composition further comprises a perfume.
- the weight ratio between the mixture comprising the cationic surfactants and the perfume is from 99:1 to 40:60, preferably from 95:5 to 70:30, more preferably from 90:10 to 75:25.
- composition preferably further comprises water.
- the water content is preferably higher than 50% wt., more preferably higher than 80% wt., most preferably higher than 85% wt., based in the total weight of the softener composition.
- the solid residue is preferably lower than 50 wt., more preferably lower than 25% wt., even more preferably between 2 and 15% wt., based on the total weight of the softener composition.
- the composition can be dispersed in water, wherein water is deionized.
- the composition in another embodiment of the invention, can be dispersed in water, wherein water is tap water.
- the composition can be dispersed in water, wherein water has a hardness value from 0 to 800 ppm of CaCO3, from 0 to 600 ppm CaCO3, from 0 to 400 ppm CaCO3, from 0 to 200 ppm CaCO3, from 5 to 800 ppm CaCO3, from 5 to 600 ppm CaCO3, from 5 to 400 ppm CaCO3, from 5 to 200 ppm CaCO3, from 10 to 800 ppm CaCO3, from 10 to 600 ppm CaCO3, from 10 to 400 ppm CaCO3, from 10 to 200 ppm CaCO3.
- Water hardness can be defined as the concentrations of calcium and magnesium ions in water expressed in terms of calcium carbonate. Whereas deionized water is water that has been treated to have a water hardness of 0 ppm CaCO3 or lower than 5 ppm CaCO3, preferably lower than 3 ppm CaCO3, water available at households, that is, tap water has typically hardness values from 10 to 400 ppm of CaCO3.
- Water hardness can be measured according to UNE-EN 12829.
- the composition can be dispersed in water at a temperature from 5°C to 40°C, preferably from 10 to 30°C, more preferably from 15°C to 25°C.
- the composition is homogeneously and easily dispersed in water.
- the composition further comprises a thickener , e.g., a thickening polymer.
- a thickener e.g., a thickening polymer.
- the weight ratio the cationic surfactant mixture to the thickener is preferably from 150:1 to 10:5, more preferably from 100:1 to 10:2.
- a thickener may be added to increase the viscosity of the composition. Suitable thickeners are, e.g.
- PEG-150 distearate Hydroxyethyl cellulose, hydroxymethyl cellulose and derivatives thereof, PEG-120 Methyl Glucose Dioleate, PEG-120 Methyl Glucose Trioleate, (and) propanediol, and ethoxylated Sorbitan Triisostearate (e.g., PEG-160 Sorbitan Triisostearate, such as Kaopan TW IS-559S from Kao Chemicals Europe, S.L.), and copolymers of acrylamide and dimethyl amino ethyl methacrylate methyl chloride cross- methylene bisacrylamide (such as FLOSOFT 222 manufactured by SNF).
- Sorbitan Triisostearate e.g., PEG-160 Sorbitan Triisostearate, such as Kaopan TW IS-559S from Kao Chemicals Europe, S.L.
- the perfume is mixed with the mixture of cationic surfactants before the dispersion of the composition in water.
- the perfume is mixed with the mixture of the invention under constant stirring at a temperature from 5°C to 40°C.
- the premix of perfume and mixture of cationic surfactants is then added to water, under constant stirring, at a temperature from 5°C to 40°C, preferably from 10°C to 30°, more preferably from 15°C to 25°C.
- the mixture of the perfume with the mixture of the invention including the cationic surfactants as well as the quaternary ester ammonium compound(s) is a clear viscous liquid that can be directly, and easily dispersed in water, wherein such diluted formulations are stable upon storage.
- the composition further comprises an encapsulated perfume, which is different from the perfume hereinabove described.
- the perfume is encapsulated in a biodegradable microcapsule, more preferably the microcapsule is based on chitosan.
- the encapsulated perfume is added to the mixture together with the perfume in the premix, alternatively, it is added to the mixture after the dispersion with water.
- compositions exhibit advantageous storage stability.
- the softener compositions are stable upon storage at a range of temperature from 5°C to 40°C, preferably from 10°C to 30°C, more preferably from 15°C to 25°C for at least 2 months, preferably at least 3 months, more preferably at least 6 months.
- the softener composition can be dispersed in water and is stable upon storage for at least three months, and the mixture of cationic surfactant is characterized by a molar ratio of monoacid/diacid (b1/b2) from 3.0 to 4.0, and the saponification value is from 150 to 180 mg KOH/g.
- the softener composition can be dispersed in water and is stable upon storage for at least three months, and the mixture of cationic surfactant is characterized by a molar ratio of monoacid/diacid (b1/b2) from 3.0 to 4.0, the iodine value of the monocarboxylic acid is from 65 to 85, and the saponification value is from 150 to 180 mg KOH/g.
- the softener composition may have a viscosity at 20°C of 5 to 500 cps, as measured on a Brookfield LVT viscometer with spindle 2 at 60 rpm.
- the softener composition of the invention is an aqueous dispersion including the mixture of cationic surfactants and quaternary ester ammonium compound, as defined hereinabove:
- the present invention further provides a concentrated softener composition
- a concentrated softener composition comprising the mixture of cationic surfactants and as described hereinabove, and having a water content lower than 50% wt., preferably lower than 30% wt., more preferably lower than 10% wt., even more preferably lower than 5% wt, most preferably lower than 1% wt.
- concentrated refers to this compositions having a content of water below 50% wt.
- the concentrated composition comprises 40% wt., or more, preferably from 40% to 90% wt., more preferably from 70 to 90% wt. of the mixture of cationic surfactant.
- the concentrated softener composition further comprises a perfume, preferably wherein the perfume consists of one or more substance(s) and/or the ClogP of the perfume substance (s) is from 0.5 to 8, preferably from 2 to 7.
- concentrated composition is one wherein the weight ratio between the mixture of cationic surfactant and quaternary ester ammonium compound, as defined hereinabove, and the perfume is from 99:1 to 40:60, preferably from 95:5 to 70:30, more preferably from 90:10 to 75:25.
- the invention provides a concentrated softener composition suitable for preparing a domestic softener formulation by dilution.
- compositions are preferably liquid at temperatures from 5°C to 80°C, preferably from 10 to 60°C, more preferably from 15°C to 40°C, even more preferably from 15°C to 25°C; comprises the mixture including the cationic surfactant mixture as described hereinabove, and has a water content lower than 50% wt., preferably lower than 30%wt., more preferably lower than 10% wt., even more preferably lower than 5%wt, most preferably lower than 1% wt.
- compositions are suitable for being dispersed in cold water (for instance by consumer at home), they are suitable for preparing a unit dose softener and/or they can be directly added into the washing machine (i.e with automatic dosing washing machines or auto-dosing bottles).
- the concentrated softener composition can be dispersed in water at a temperature from 5°C to 40°C, preferably from 10 to 30°C, more preferably from 15°C to 25°C.
- the concentrated softener composition can be dispersed in tap water, such as water directly obtained from a faucet or tap connected to the main supply of the local water system, that has not been distilled and/or deionized.
- the concentrated softener composition can be dispersed in water, wherein the water has a hardness value from 0 to 800, from 0 to 600 ppm CaCO3, from 0 to 400 ppm CaCO3, from 0 to 200 ppm CaCO3, from 5 to 800 ppm CaCO3, from 5 to 600 ppm CaCO3, from 5 to 400 ppm CaCO3, from 5 to 200 ppm CaCO3, from 10 to 800 ppm CaCO3, from 10 to 600 ppm CaCO3, from 10 to 400 ppm CaCO3, from 10 to 200 ppm CaCO3.
- compositions exhibit advantageous storage stability.
- the concentrated softener compositions are stable upon storage at a range of temperature from 5°C to 40°C, preferably from 10°C to 30°C, more preferably from 15°C to 25°C for at least 2 months, preferably at least 3 months, more preferably at least 6 months.
- the concentrated softening compositions are suitable for being dispersed in cold water by consumer at home, wherein obtained compositions are stable for at least three months, wherein the mixture of cationic surfactant is characterized by a molar ratio of monoacid/diacid (b1/b2) from 3.0 to 4.0, and the saponification value is from 150 to 180 mg KOH/g.
- the concentrated softening compositions are suitable for being dispersed in cold water by consumer at home, wherein obtained compositions are stable for at least three months, wherein the mixture of cationic surfactant is characterized by a molar ratio of monoacid/diacid (b1/b2) from 3.0 to 4.0, the iodine value of the monocarboxylic acid is from 65 to 85 and the saponification value is from 150 to 180 mg KOH/g.
- the concentrated softener compositions may have a viscosity at 20 °C of 200-50,000 cps, as measured on a Brookfield LVT viscometer with spindle 2 at 60 rpm or with spindle 4 at 12 rpm.
- such compositions are non-newtonian and have a viscosity of 200 to 5,000 mPas as measured on a Brookfield LVT viscometer with spindle 4 at 12 rpm, optionally 200 to 800 mPas; or are newtonian and have a viscosity of 200 to 800 mPas as measured on a Brookfield LVT viscometer with spindle 2 at 30 rpm.
- the composition further comprises an encapsulated perfume, which is different from the perfume hereinabove described.
- the perfume is encapsulated in a biodegradable microcapsule, more preferably the microcapsule is based on chitosan.
- the encapsulated perfume is added to the mixture after the dispersion with water.
- the concentrated softening compositions is suitable for preparing a unit dose softener contained in a water-soluble pouch.
- the water soluble pouch wherein the concentrated softener is contained is in form of tablet or capsule.
- the water-soluble pouch is formed or comprises polyvinyl alcohol.
- the concentrated softening composition is suitable for preparing a unit dose softener contained in a water-soluble pouch, wherein obtained compositions are homogenously and easily dispersed once added in situ (i.e., in the washing machine), without agglomerated particles which would not allow a good softening effect of the composition, wherein, in the definition of the cationic mixture, the molar ratio of monoacid/diacid (b1/b2) is from 3.0 to 4.0, and the saponification value is from 150 to 180mg KOH/g.
- the concentrated softening compositions are suitable for preparing a unit dose softener contained in a water-soluble pouch, wherein obtained compositions are homogenously and easily dispersed once added in situ (i.e., in the washing machine), without agglomerated particles which would not allow a good softening effect of the composition, wherein in the definition of the cationic mixture the molar ratio of monoacid/diacid (b1/b2) from 3.0 to 4.0, the iodine value of the monocarboxylic acid is from 65 to 85 and the saponification value is from 150 to 180 mg KOH/g.
- the softener composition can be used to soften fabrics by treating the fabric with the composition. This can be done during the non-rinse and rinse process using a liquid fabric softener.
- the method for conditioning (i.e., softening) textiles or fabrics comprises the steps of contacting one or more fabric articles with the softener composition of the invention at one or more points during the laundering process, and allowing the fabric articles to dry or mechanically tumble-drying them.
- the use of the softener composition of the invention for the conditioning treatment of textiles is another embodiment of the invention.
- a stable softener composition refers to a composition which maintains its viscosity, within an interval of time, immediately after its preparation and after storage.
- compositions are stable for at least 2 months, preferably at least 3 months, even more preferably at least 6 months.
- a stable composition which "maintains its viscosity within an interval of time” encompasses variations up to ⁇ 10%, up to ⁇ 9%, up to ⁇ 8%, up to ⁇ 7%, up to ⁇ 6%, up to ⁇ 5%, up to ⁇ 4%, up to ⁇ 3%, up to ⁇ 2%, or up to 1% in the viscosity value of the composition immediately after its preparation.
- viscosity is measured on a Brookfield LVT viscometer at 20 °C with a spindle 2 at 30 or 60 rpm (preferably: for low viscosities), or with a spindle 4 at 12 rpm (preferably: for high viscosities).
- iodine number (or “iodine value”, or “iodine adsorption value”, commonly abbreviated as IV) describes the degree of unsaturation, e.g., of a fatty acid, and can be determined according to EN 14111:2003.
- Iodine value is the mass of iodine in grams that is consumed by 100 grams of a chemical substance or composition. Iodine value is commonly used to determine the amount of unsaturation in fats, oils and waxes. Thus, the iodine value is suitable to determine the degree of unsaturations of the carboxylic acids of the present invention.
- iodine value can be calculated from the original source of fatty acid (i.e. the carboxylic acids), alternatively it can be measured from the composition as hereinabove defined, comprising the mixture of cationic surfactants and the quaternary ester ammonium compound.
- room temperature is understood as a temperature from 5 to 40°C, preferably from 10 to 30°C.
- cold water is understood as water at a temperature from 5°C to 40°C, preferably from 10°C to 30°C, more preferably from 15°C to 25°C.
- ppm of CaCO3 is 0 or lower than 5 ppm CaCO3, preferably lower than 3 ppm CaCO3.
- to disperse is understood as to the formation of a dispersion, that is, a system wherein particles of one material are distributed evenly in a continuous phase of another material, thus, allowing the formation of a colloid or suspension.
- a dispersion that is, a system wherein particles of one material are distributed evenly in a continuous phase of another material, thus, allowing the formation of a colloid or suspension.
- the mixture of cationic surfactants and quaternary ester ammonium compounds are evenly distributed in water obtaining a dispersion.
- the final appearance of the obtained dispersion is opaque, homogeneous and liquid.
- ClogP refers to the calculated octanol/water partitioning coefficient (P) of a fragrance ingredient expressed in the form of its logarithm to the base 10.
- the octanol/water partitioning coefficient of a fragrance ingredient is the ratio between its equilibrium concentrations in octanol and in water.
- Clog values can be calculated using the fragment approach as described in " Partition Coefficients and Their Uses" by A Leo, C Hansch and D Elkins in Chem. Rev. vol 71 (6) pages 525-616 (1971 ).
- the Clog values can also be calculated by the "CLOGP” program available within the Chemoffice Ultra Software version 9 available from CambridgeSoft Corporation, 100 CambridgePark Drive, Cambridge, MA 02140 USA or CambridgeSoft Corporation, 8 Signet Court, Swanns Road, Cambridge CB5 8LA UK.
- ClogP values can also be calculated in US EPA CompTox Chemicals Dashboard (https: // comptox.epa.gov/dashboard, v2.2.1) .
- a fabric-textile material comprises materials such natural, synthetic and artificial fibres.
- Natural fibres include vegetal fibres such cotton, or keratinic fibres (wool, silk).
- Some common man-made fibres, are polyester, polyamide, acrylic, modal, polyurethane, viscose and mixtures thereof.
- the first part of the Examples section refers to the preparation of the mixture of cationic surfactants.
- the second part refers to the preparation of a fabric softener composition according to the invention and the determination of the stability of the dispersion.
- a yellowish liquid product from the esterification was obtained, consisting essentially of a mixture of unesterified fatty acids and adipic acid, mono-, di- and triesterified triethanolamine with fatty acids, mono-, di- and triesterified triethanolamine with adipic acid or a combination thereof, together with unreacted triethanolamine.
- a yellowish liquid product from the esterification was obtained, consisting essentially of a mixture of unesterified fatty acids and adipic acid, mono-, di- and triesterified triethanolamine with fatty acids, mono-, di- and triesterified triethanolamine with adipic acid or a combination thereof, together with unreacted triethanolamine.
- a yellowish liquid product from the esterification was obtained. consisting essentially of a mixture of unesterified fatty acids mono-, di- and triesterified triethanolamine.
- Example A according to the invention, as well as it showed stable formulations (showing no- or little- variations in viscosity), at different temperatures, during a prolonged period of time.
- Example A Dispersion time in water 20°HF ⁇ 15 seconds Appearance of dispersion Opaque and homogeneous Viscosity (at 5°C) (t1)24h 150 (t2)28days 148 (t3)56days 149 (t4)84days 145 Viscosity (at 20°C) (t1)24h 150 (t2)28days 152 (t3)56days 148 (t4)84days 155 Viscosity (at 40°C) (t1)24h 150 (t2)28days 152 (t3)56days 156 (t4)84days 158
- Viscosity was measured with a Brookfield LVT viscometer with spindle 2 at 60 rpm.
- composition comprising the perfume and the mixture of cationic surfactants:
Landscapes
- Chemical & Material Sciences (AREA)
- 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)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP23382901.9A EP4520812A1 (fr) | 2023-09-05 | 2023-09-05 | Formulations adoucissantes comprenant des melanges de tensioactifs cationiques |
| PCT/EP2024/074718 WO2025051798A1 (fr) | 2023-09-05 | 2024-09-04 | Formulations d'adoucissant comprenant des mélanges de tensioactifs cationiques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP23382901.9A EP4520812A1 (fr) | 2023-09-05 | 2023-09-05 | Formulations adoucissantes comprenant des melanges de tensioactifs cationiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP4520812A1 true EP4520812A1 (fr) | 2025-03-12 |
Family
ID=87933617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP23382901.9A Withdrawn EP4520812A1 (fr) | 2023-09-05 | 2023-09-05 | Formulations adoucissantes comprenant des melanges de tensioactifs cationiques |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP4520812A1 (fr) |
| WO (1) | WO2025051798A1 (fr) |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB602048A (en) * | 1945-10-12 | 1948-05-19 | Allied Colloids Bradford Ltd | Improvements in the manufacture of nitrogen compounds, in the softening of vegetable, animal or synthetic fibres and in treating baths for textile materials |
| EP0770595A1 (fr) * | 1995-10-26 | 1997-05-02 | Henkel Kommanditgesellschaft auf Aktien | Sorbitol esterquats et leur utilisation dans la préparation d'agents tensioactifs notamment des agents de soins capillaires et de soins corporels |
| WO1998049132A1 (fr) * | 1997-04-30 | 1998-11-05 | Kao Corporation | Composant adoucissant actif pour textiles et compositions adoucissantes pour textiles contenant ce composant |
| DE19751151A1 (de) * | 1997-11-19 | 1999-05-20 | Henkel Kgaa | Klare Weichspüler mit mikroemulgierten Parfümölen |
| EP1136471A1 (fr) | 2000-03-22 | 2001-09-26 | Kao Corporation, S.A. | Dérivés d'esters à partir d'alcanolamines, d'acides dicarboxyliques et d'alcools gras et tensioactifs cationiques résultants |
| DE10237031A1 (de) * | 2002-08-13 | 2004-02-26 | Cognis Deutschland Gmbh & Co. Kg | Quaternierte Fettsäurealkanolaminestersalze aur Basis konjugierter Linolsäure |
| WO2016096614A1 (fr) | 2014-12-17 | 2016-06-23 | Henkel Ag & Co. Kgaa | Agents d'entretien transparents pour textiles |
| EP3130656A1 (fr) * | 2015-08-06 | 2017-02-15 | Henkel AG & Co. KGaA | Fluides pauvres en eau pour le traitement de textiles, contenant au moins un composé cationique spécial et au moins un tensio-actif supplémentaire |
-
2023
- 2023-09-05 EP EP23382901.9A patent/EP4520812A1/fr not_active Withdrawn
-
2024
- 2024-09-04 WO PCT/EP2024/074718 patent/WO2025051798A1/fr active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB602048A (en) * | 1945-10-12 | 1948-05-19 | Allied Colloids Bradford Ltd | Improvements in the manufacture of nitrogen compounds, in the softening of vegetable, animal or synthetic fibres and in treating baths for textile materials |
| EP0770595A1 (fr) * | 1995-10-26 | 1997-05-02 | Henkel Kommanditgesellschaft auf Aktien | Sorbitol esterquats et leur utilisation dans la préparation d'agents tensioactifs notamment des agents de soins capillaires et de soins corporels |
| WO1998049132A1 (fr) * | 1997-04-30 | 1998-11-05 | Kao Corporation | Composant adoucissant actif pour textiles et compositions adoucissantes pour textiles contenant ce composant |
| DE19751151A1 (de) * | 1997-11-19 | 1999-05-20 | Henkel Kgaa | Klare Weichspüler mit mikroemulgierten Parfümölen |
| EP1136471A1 (fr) | 2000-03-22 | 2001-09-26 | Kao Corporation, S.A. | Dérivés d'esters à partir d'alcanolamines, d'acides dicarboxyliques et d'alcools gras et tensioactifs cationiques résultants |
| DE10237031A1 (de) * | 2002-08-13 | 2004-02-26 | Cognis Deutschland Gmbh & Co. Kg | Quaternierte Fettsäurealkanolaminestersalze aur Basis konjugierter Linolsäure |
| WO2016096614A1 (fr) | 2014-12-17 | 2016-06-23 | Henkel Ag & Co. Kgaa | Agents d'entretien transparents pour textiles |
| EP3130656A1 (fr) * | 2015-08-06 | 2017-02-15 | Henkel AG & Co. KGaA | Fluides pauvres en eau pour le traitement de textiles, contenant au moins un composé cationique spécial et au moins un tensio-actif supplémentaire |
Non-Patent Citations (1)
| Title |
|---|
| A LEOC HANSCHD ELKINS, CHEM. REV., vol. 71, no. 6, 1971, pages 525 - 616 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2025051798A1 (fr) | 2025-03-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6465419B1 (en) | Esters derived from alkanolamines, dicarboxylic acids and fatty alcohols and the cationic surfactants obtainable therefrom | |
| EP2809758B1 (fr) | Composition active d'adoucissant textile | |
| CN101600785B (zh) | 免漂洗织物软化剂 | |
| US6562780B2 (en) | Esters derived from alkanolamines, dicarboxylic acids and fatty alcohols and the cationic surfactants obtainable therefrom | |
| AU2011225788B2 (en) | Liquid concentrated fabric softener composition | |
| JP2023548362A (ja) | トランス脂肪酸から部分的に誘導されるエステルクアットを含む液体コンディショニング組成物 | |
| US20260055338A1 (en) | Concentrated liquid esterquat compositions | |
| WO2023166043A1 (fr) | Formulations adoucissantes pour maintenir ou améliorer l'évacuation de l'humidité | |
| JP4409172B2 (ja) | ノニオン界面活性剤を含有する繊維柔軟剤組成物 | |
| EP4520812A1 (fr) | Formulations adoucissantes comprenant des melanges de tensioactifs cationiques | |
| WO2023166041A1 (fr) | Formulations d'adoucissant transparent | |
| EP4520810A1 (fr) | Utilisation d'un mélange de tensioactifs cationiques pour disperser un composant d'ester ammonium quaternaire dans l'eau | |
| US20250179389A1 (en) | Dispersible softener formulations and unit doses | |
| EP4520811A1 (fr) | Utilisation de parfum pour disperser un mélange cationique dans l'eau | |
| EP4574944A1 (fr) | Formulations d'adoucissants à activité biocide | |
| JPWO2023166042A5 (fr) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN PUBLISHED |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC ME MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 20250913 |