EP3884019B1 - Zusammensetzungen zur häuslichen pflege - Google Patents

Zusammensetzungen zur häuslichen pflege

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Publication number
EP3884019B1
EP3884019B1 EP18837087.8A EP18837087A EP3884019B1 EP 3884019 B1 EP3884019 B1 EP 3884019B1 EP 18837087 A EP18837087 A EP 18837087A EP 3884019 B1 EP3884019 B1 EP 3884019B1
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EP
European Patent Office
Prior art keywords
esterquat
under
mixture
group
carbodiimide
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EP18837087.8A
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English (en)
French (fr)
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EP3884019A1 (de
Inventor
Hongwei SHEN
Charles Schramm Jr.
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Colgate Palmolive Co
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Colgate Palmolive Co
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Publication of EP3884019A1 publication Critical patent/EP3884019A1/de
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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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen

Definitions

  • Fabric care compositions e.g. fabric conditioners
  • fabric softeners may be regarded as an after-treatment laundry aid.
  • Machine washing puts great mechanical stress on textiles, particularly natural fibers such as cotton and wool.
  • the fibers at the fabric surface are squashed and frayed, and this condition hardens while drying the laundry in the air, giving the laundry a harsh feel.
  • Adding a liquid fabric softener to the final rinse (rinse-cycle softener) results in the laundry that feels softer.
  • Fabric softeners are usually either in the form of a liquid, which is added to the washing machine during the rinse cycle (either by the machine itself or through use of a dispensing ball); or as a dryer sheet which is added to the moist laundry at the beginning of the dryer cycle. Liquid fabric softeners can be added manually during the rinse cycle or automatically if the machine has a dispenser designed for this purpose.
  • Fabric softeners coat the surface of fabric with chemical compounds that are electrically charged, causing threads to stand up from the surface and thereby imparting a softer and fluffier texture.
  • Cationic softeners bind by electrostatic attraction to the negatively charged groups on the surface of the fibers and neutralize their charge. The long aliphatic chains then line up towards the outside of the fiber, imparting lubricity.
  • Rinse-cycle softeners usually contain cationic surfactants of the quaternary ammonium type as the main active ingredient. Cationic surfactants adhere well to natural fibers (wool, cotton), but less so to synthetic fibers. Cationic softeners are incompatible with anionic surfactants in detergents because they combine with them to form a solid precipitate. This requires that the softener is added in the rinse cycle. Fabric softener reduces the absorbency of textiles, which adversely affects the function of towels and microfiber cloth.
  • DTDMAC ditallowdimethylammonium chloride
  • DSDMAC distearyldimethylammonium chloride
  • a domestic laundry fabric softener is disclosed in U.S. Patent No. 3,915,867 . That patent teaches a self-emulsifying domestic laundry fabric active softener base comprised of N-methyl, N,N-di-( ⁇ -C 14 -C 18 acyloxy ethyl), N- ⁇ -hydroxy ethyl ammonium metho sulfate characterized by good softening, outstanding whiteness-retention and excellent rewetting properties and has a light color having an index on the Gardner scale in the range of about 1 to 2.
  • the active softener base is dispersed in an inert vehicle such as isopropanol and/or water and may be intermixed with other additives, such as perfumes, nonionic wetting agents, optical brighteners, etc.
  • Esterquats a class of cationic fabric softeners, are reviewed by S. Mishra, V. K. Tyagi in J. Oleo Sci., vol. 56, iss. 6, pp 269 to 276 .
  • Esterquats which are quaternary ammonium compounds having two long (C 16 -C 18 ) fatty acid chains with 2 weak ester linkages, represent a new generation of fabric softening agents, having replaced the dialkyldimethylammonium salts (e.g., DTDMAC and DSDMAC).
  • the inclusion of ester linkages into the aliphatic chains has significantly improved the kinetics of biodegradation of the cationic surfactants, lowering the environmental exposure levels.
  • This generation of fabric softening agents combines a good environmental profile with the structural features required for an effective fabric conditioner.
  • the paper reviewed the synthesis, types, actives combines a good environmental profile with the structural features required for a properties and applications of esterquats.
  • Esterquats are commonly used in fabric conditioners, however, they have a drawback: esterquats tend to hydrolyze at elevated temperatures. Such elevated temperatures are typically encountered in tropical climates. Additionally, such elevated temperatures are frequently encountered during the transportation vessels such as in hot trucks, and intermodal containers. Further such elevated temperatures are frequently encountered in warehouses. Finally, such elevated temperatures are sometimes found in laundry rooms, Laundromats, and facilities where heat is generated during the washing phase and the drying phase of doing laundry.
  • One of the degradation pathways of the fabric conditioner is the hydrolysis of esterquat, to release free fatty acids. Free fatty acids have low solubilities in water and tend to precipitate out of the fabric conditioner as white fatty flakes. Such precipitation is undesirable from both efficacy and aesthetic considerations.
  • WO 98/00500 A1 discloses a composition comprising a peptide or protein deposition aid having a high affinity for fibres or a surface and attached/adsorbed to the peptide or protein deposition aid a benefit agent, wherein the composition effectively deposits the benefit agent onto fabric during the wash cycle.
  • EP 3 342 395 A2 discloses a composition for surface modification, wherein the composition for surface modification contains a particular carbodiimide-based compound, thus forms a covalent bond without damaging skin, hair, or fabric, and semipermanently provides desired skin or hair surface modification effects or fabric care effects.
  • WO 2009/030601 A1 discloses compositions comprising unsaturated fatty chains that have reduced or eliminated base off-odour with the incorporation of a photobleach.
  • US 2014/0208525 A1 discloses a method for reducing force needed for ironing a fabric comprising laundering the fabric with a composition comprising a linear polyether having a weight average molecular weight less than 5000 that is terminated with -N-(-CH 2 -CH(OH)-CH 2 -Cl) 2 , wherein the linear polyether is deposited on the fabric and reduces the force needed for ironing
  • the present invention is directed to a fabric conditioner composition
  • a fabric conditioner composition comprising an esterquat, and a carbodiimide, wherein the esterquat is a quaternary ammonium compound having a formula as defined in the claims.
  • Advantages of the present invention is a reduction of the hydrolysis of esterquats in the fabric conditioners, reduction of residual fatty odor, and mitigation of fatty acid precipitation.
  • organic groups R and R' are each independently a C 1-6 alkyl group, an aryl group, a cycloalkyl group, or an aminoalkene group.
  • C 1-6 alkyl group as used herein includes saturated hydrocarbyl groups with one to six carbons that are straight chains, branched, and alicyclic.
  • carbodiimides with small (i.e. , 6 carbons or less) hydrocarbyl groups are preferred.
  • Aryl group may be phenyl, benzyl, phenyl substituted with one or more small hydrocarbyl groups, benzyl, benzyl substituted with one or more small hydrocarbyl groups, and mixtures thereof.
  • Cycloalkyl group is a hydrocarbyl group that comprises a cyclic saturated component.
  • the cycloalkyl group is a cyclic saturated hydrocarbyl.
  • the cycloalkyl group may be a substituted cyclic saturated hydrocarbyl, a linear group that is substituted with a cyclic saturated group
  • one or both of the organic groups R and R' are an aminoalkene group.
  • aminoalkene includes aminoalkene that is unsubstituted on the nitrogen, aminoalkene that is substituted on the nitrogen by one further alkyl group, and aminoalkene that is substituted on the nitrogen by two further alkyl groups.
  • the aminoalkene group is -(CH 2 ) x NR m R n ; wherein x is a number from 1 to 5, and R m and R n are each independently H or C 1-6 alkyl groups.
  • the organic groups R and R' are identical.
  • the organic groups R and R' are different.
  • Examples of carbodiimides wherein R ⁇ R' includes N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide methiodide, and mixtures thereof.
  • N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide is water soluble.
  • the carbodiimide is water dispersible.
  • the carbodiimide is defined in the claims. Many dialkylcarbodiimides prefer the monomeric form. Many diarylcarbodiimides upon standing convert to dimers, and to polymers at room temperature.
  • the carbodiimide of the present invention may be prepared by any of the commercially available routes, including preparation by dehydrosulfurization of thioureas, or preparation from isocyanates.
  • An esterquat comprises a quaternary ammonium cation comprising fatty acid chains linked by weak ester linkages. Esterquats are useful as fabric softening agents, having replaced the dialkyldimethylammonium salts. The ester linkages in the aliphatic chains significantly improves the kinetics of biodegradation of the cationic surfactants, lowering the environmental exposure levels.
  • an esterquat can also be a quaternary ammonium compound of formula [R a R b R c R d N + ][X - ], wherein R a , R b and R c are each independently -(CH 2 ) g -R e , wherein R e is OH or an alkanoyloxy group containing from 8 to 22 carbon atoms; R d is a hydrocarbyl group comprising 1 to 12 carbon atoms; g is a number from 1 to 3; and X - is a softener compatible anion.
  • the esterquat may be a monoesterquat, a diesterquat, or a triesterquat. Further the esterquat may be a mixture of esterquats.
  • An esterquat can be a mixture of about 20 wt% to about 40 wt% of monoesterquat, about 50 wt% to about 65 wt% of diesterquat, and about 10 wt% to about 25 wt% triesterquat.
  • the esterquat as defined in the claims is a quaternary ammonium cation comprising fatty acid chains linked by weak ester linkages.
  • X - the counterion for the quaternary ammonium cation, is a softener compatible anion.
  • suitable softener compatible anions include chloride, bromide, methylsulfate, ethylsulfate, sulfate, phosphate, or nitrate, formate, lactate, benzoate, and mixtures thereof.
  • the present invention is directed to a fabric conditioner composition
  • a fabric conditioner composition comprising an esterquat, a carbodiimide, and optionally, additional ingredients.
  • ingredients include fragrances, surfactants, thickening polymers, colorants, clays, buffers, chelating compounds, silicones, fatty alcohols, and fatty esters
  • the invention relates to a fabric conditioner composition
  • a fabric conditioner composition comprising an esterquat, and a carbodiimide as defined in the claims.
  • the carbodiimide may be selected from the group consisting of N,N'-dicyclohexylcarbodiimide, N,N'-diisopropylcarbodiimide, N,N'-diphenylcarbodiimide, N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide methiodide, N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, and mixture thereof.
  • the carbodiimide may be 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, and can generally be an adduct thereof, a dimer thereof, a polymer thereof, and mixture thereof.
  • the carbodiimide may be a water disperable carbodiimide.
  • the esterquat is a quaternary ammonium compound of formula: [R 1 R 2 R 3 N + -(CH 2 ) q -O-CO-R 4 ][X - ] wherein: R 4 is an aliphatic hydrocarbyl group comprising 8 to 22 carbon atoms; R 2 and R 3 are each independently -(CH 2 ) s -R 5 ; R 5 is an alkoxy carbonyl group containing from 8 to 22 carbon atoms, benzyl, phenyl, C 1-4 alkyl substituted phenyl, OH, or H; R 1 is -(CH 2 )t-R 6 ; R 6 is benzyl, phenyl, C 1-4 alkyl substituted phenyl, OH, or H; q, s, and t are each independently a number from 1 to 3; and X - is a softener compatible anion.
  • an esterquat can also be a quaternary ammonium compound of formula [R a R b R c R d N + ][X - ], wherein R a , R b and R c are each independently -(CH 2 ) g -R e , wherein R e is OH or an alkoxy hydrocarbyl group containing from 8 to 22 carbon atoms; R d is a hydrocarbyl group comprising 1 to 12 carbon atoms; g and h are each independently an integer from 1 to 3; and X - is a softener compatible anion, wherein at least one of the hydrocarbyl group is an aliphatic group containing 0 to 3 double bonds.
  • an esterquat can also be a quaternary ammonium compound of formula [R a R b R c R d N + ][X - ], wherein R a , R b and R c are each independently -(CH 2 ) g -R e , wherein R e is OH or an alkoxy hydrocarbyl group containing from 8 to 22 carbon atoms; R d is a hydrocarbyl group comprising 1 to 12 carbon atoms; g and h are each independently an integer from 1 to 3; and X - is a softener compatible anion, wherein at least one of the hydrocarbyl group is an aliphatic group containing 0 to 3 double bonds, wherein the aliphatic group is linear.
  • the esterquat is a quaternary ammonium compound of formula [R 1 R 2 R 3 N + -(CH 2 ) q -O-CO-R 4 ][X - ], wherein R 4 is an aliphatic hydrocarbyl group comprising 8 to 22 carbon atoms; R 2 and R 3 are each independently -(CH 2 ) s -R 5 , wherein R 5 is an alkoxy carbonyl group containing from 8 to 22 carbon atoms, benzyl, phenyl, C 1-4 alkyl substituted phenyl, OH, or H; R 1 is - (CH 2 ) t -R 6 , wherein R 6 is benzyl, phenyl, C 1-4 alkyl substituted phenyl, OH, or H; q, s, and t are each independently a number from 1 to 3; and X - is a softener compatible anion.
  • the fabric conditioner composition comprising an esterquat, a carbodiimide, may further comprise a cationic surfactant.
  • the esterquat may be a mixture of about 20 wt% to about 40 wt% of monoesterquat, about 50 wt% to about 65 wt% of diesterquat, and about 10 wt% to about 25 wt% triesterquat.
  • ranges are used as shorthand for describing each and every value that is within the range. Any value within the range can be selected as the terminus of the range.
  • mixture is to be interpreted broadly. It refers to a solution, an emulsion, a dispersion, a mixture displaying the Tyndall effect, or any other homogeneous mixture. Under one embodiment, the mixture is shelf stable.
  • mixture refers to a mixture of the aforementioned ingredients with each other, a mixture of any of aforementioned ingredients with other ingredients that are not aforementioned, and to a mixture of several aforementioned ingredients with other ingredients that are not aforementioned.
  • any member in a list of species that are used to exemplify or define a genus may be mutually different from, or overlapping with, or a subset of, or equivalent to, or nearly the same as, or identical to, any other member of the list of species. Further, unless explicitly stated, such as when reciting a Markush group, the list of species that define or exemplify the genus is open, and it is given that other species may exist that define or exemplify the genus just as well as, or better than, any other species listed.
  • the chemical functional groups are in their adjective form; for each of the adjective, the word "group” is assumed.
  • the adjective "cyclopropyl” without a nouns thereafter, should be read as "a cyclopropyl group”.
  • the present invention is directed to a fabric conditioner composition comprising an esterquat, and a carbodiimide as defined in the claims.
  • a common problem with many fabric conditioners is that they tend to degrade at high temperatures. Such high temperatures are frequently encountered in tropical area, as well as in self-service laundry facilities with a large number of washers and dryers.
  • One of the degradation pathways is the hydrolysis of esterquat, a fabric softening agent, to release free fatty acids. Free fatty acids have low solubilities in water, and tend to precipitate out of the fabric conditioner as white fatty flakes. Such precipitation is undesirable from both efficacy and aesthetic considerations.
  • One of the advantages of the present invention is that the use of carbodiimides in a fabric conditioner reduces the hydrolysis of esterquats in the fabric conditioners.
  • one advantage of the present invention is that the use of carbodiimides in a fabric conditioner reduces residual fatty odor.
  • Another advantage of the present invention is that the use of carbodiimides in a fabric conditioner mitigates the problem with fatty acid precipitation.
  • This conjugation forms an o-acylisourea ester.
  • the acylisourea ester is an active ester that may further react. Further reactions of the acylisourea may occur with primary amines to form isourea byproducts.
  • the present invention is directed to a fabric conditioner comprising an esterquat and a carbodiimide as defined in the claims.
  • organic groups R and R' are each independently a C 1-6 alkyl group, an aryl group, a cycloalkyl group, or an aminoalkene group.
  • C 1-6 alkyl group as used herein includes saturated hydrocarbyl groups with one to six carbons, that are straight chains, branched, and alicyclic.
  • Examples of a suitable C 1-6 alkyl group include -CH 3 , -C 2 H 5 , -C 3 H 7 , -C 4 H 9 , -C 5 H 11 , -C 6 H 13 , and mixtures thereof.
  • Suitable straight chain alkyl groups include methyl, ethyl, n -propyl, n- pentyl, n -hexyl, and mixtures thereof.
  • Examples of a suitable alkyl group include propyl, pentyl, hexyl, and mixtures thereof, wherein each of the groups is not linear.
  • Examples of a suitable C 1-6 alkyl group include 1-methylpropyl; sec -butyl; 2-methylpropyl; iso -butyl; 1,1-dimethylethyl; tert -butyl; 1-methylbutyl; sec -pentyl; 2-methylbutyl; 3-methylbutyl; 1-ethylpropyl; 3-pentyl; 1,1-dimethylpropyl; tert- pentyl; 1,2-dimethylpropyl; 2,2-dimethylpropyl; neopentyl; 1-methylpentyl; 2-methylpentyl; 3-methylpentyl; 4-methylpentyl; iso -amyl; 1,1-dimethylbutyl; 1,2-dimethylbutyl; 1,3-dimethylbutyl; 2,
  • carbodiimides with small (i.e. , 6 carbons or less) hydrocarbyl groups are preferred.
  • an aryl group includes phenyl, benzyl, phenyl substituted with one or more small hydrocarbyl groups, benzyl, benzyl substituted with one or more small hydrocarbyl groups, and mixtures thereof.
  • the aryl group has 12 carbons or less.
  • the aryl group has 10 carbons or less.
  • the aryl group has 8 carbons or less.
  • the aryl group has 6 carbons.
  • Cycloalkyl group is hydrocarbyl group that comprises a cyclic saturated component.
  • the cycloalkyl group is a cyclic saturated hydrocarbyl.
  • suitable cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and mixtures thereof.
  • the cycloalkyl group is a substituted cyclic saturated hydrocarbyl.
  • a cycloalkyl group include methylcyclopropyl, methylcyclobutyl, methylcyclopentyl, methylcyclohexyl, methylcycloheptyl, ethylcyclopropyl, ethylcyclobutyl, ethylcyclopentyl, ethylcyclohexyl, ethylcycloheptyl, dimethylcyclopropyl, dimethylcyclobutyl, dimethylcyclopentyl, dimethylcyclohexyl, dimethylcycloheptyl, diethylcyclopropyl, diethylcyclobutyl, diethylcyclopentyl, diethylcyclohexyl, diethylcycloheptyl, and mixtures thereof.
  • the cycloalkyl group is a linear group that is substituted with a cyclic saturated group.
  • the substitution may occur at the end of the chain, or anywhere along the chain.
  • Examples of a linear group that is substituted with a cyclic saturated group include cyclopropylmethylene, cyclopropylethylene, cyclopropylpropylene, cyclopropylbutylene, cyclobutylmethylene, cyclobutylethylene, cyclobutylpropylene, cyclobutylbutylene, cyclopentylmethylene, cyclopentylethylene, cyclopentylpropylene, cyclopentylbutylene, cyclohexylmethylene, cyclohexylethylene, cyclohexylpropylene, cyclohexylbutylene, 1-cyclopropylethyl, 2-cyclopropylethyl, 1-cyclobutylethyl, 2-cyclobutyle
  • one or both of the organic groups R and R' are an aminoalkene group.
  • aminoalkene includes aminoalkene that is unsubstituted on the nitrogen, aminoalkene that is substituted on the nitrogen by one further alkyl group, and aminoalkene that is substituted on the nitrogen by two further alkyl groups.
  • the aminoalkene group is -(CH 2 ) x NR m R n ; wherein x is a number from 1 to 5, and R m and R n are each independently H or C 1-6 alkyl groups.
  • Examples of -(CH 2 ) x NR m R n wherein x is a number from 1 to 5, and R m and R n are each independently H or C 1-6 alkyl, includes aminomethylene, methylaminomethylene, ethylaminomethylene, propylaminomethylene, butylaminomethylene, pentylaminomethylene, hexylaminomethylene, dimethylaminomethylene, methylethylaminomethylene, methylpropylaminomethylene, methylbutylaminomethylene, methylpentylaminomethylene, methylhexylaminomethylene, diethylaminomethylene, ethylpropylaminomethylene, ethylbutylaminomethylene, ethylpentylaminomethylene, ethylhexylaminomethylene, dipropylaminomethylene, propylbutylaminomethylene, propylpentylaminomethylene, propylhexylaminomethylene, di
  • the organic groups R and R' are identical.
  • the organic groups R and R' are different.
  • Examples of carbodiimides wherein R ⁇ R' includes N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide, EDC, WSC, N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride, N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride, EDAC, EDC hydrochloride, WSC hydrochloride, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide methiodide, and mixtures thereof.
  • the compound N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide is referred to, under one embodiment, as 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.
  • the compound N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide is referred to as 3-(ethyliminomethyleneamino)-N,N-dimethylpropan-1-amine.
  • N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide is water soluble.
  • the carbodiimide is water dispersible
  • Water dispersible means that the carbodiimide mixes well with water and other ingredients in the fabric conditioner composition.
  • the phrase "water dispersible" includes any stable or semi-stable homogenous mixture. Examples of water dispersible mixture include a solution, an emulsion, a dispersion, a mixture displaying the Tyndall effect, or any other homogeneous mixture.
  • the carbodiimide is in monomeric form.
  • Polymers based on carbodiimides are formed from monomers by the following reaction.
  • the asymmetric carbodiimides polymerize into regioregular polycarbodiimides.
  • the R and R' groups prefer one or the other position on the polymer, i.e. , m ⁇ n or m >> n in the above chemical equation.
  • the asymmetric carbodiimides polymerize into regioirregular polycarbodiimides.
  • the R and R' groups have a more random position on the polymer.
  • the carbodiimide of the present invention may be prepared by any of the commercially available routes.
  • the carbodiimide is prepared by dehydrosulfurization of thioureas.
  • the desulfurization agent may be mercuric oxide as follows: (R(H)N) 2 CS + HgO ⁇ (RN) 2 C + HgS + H 2 O
  • a dehydrating agent is added to the reaction mixture.
  • the dehydration of N,N'-dialkylureas gives carbodiimides as follows: (R(H)N) 2 CO ⁇ (RN) 2 C + H 2 O
  • Examples of a dehydrating agent includes phosphorus pentoxide and p-toluenesulfonyl chloride.
  • the reaction is catalyzed by phosphine oxides.
  • 3-(Ethyliminomethyleneamino)-N,N-dimethylpropan-1-amine may be prepared by coupling ethyl isocyanate to N,N-dimethylpropane-1,3-diamine to give a urea, followed by dehydration.
  • An esterquat comprises a quaternary ammonium cation comprising fatty acid chains linked by weak ester linkages. Esterquats are useful as fabric softening agents, having replaced the dialkyldimethylammonium salts. The ester linkages in the aliphatic chains significantly improves the kinetics of biodegradation of the cationic surfactants, lowering the environmental exposure levels.
  • an esterquat can be a quaternary ammonium compound of formula [R a R b R c R d N + ][X - ], wherein R a , R b and R c are each independently -(CH 2 ) g -R e , wherein R e is OH or an alkanoyloxy group containing from 8 to 22 carbon atoms; R d is a hydrocarbyl group comprising 1 to 12 carbon atoms; g is a number from 1 to 3; and X - is a softener compatible anion.
  • the R d group is a hydrocarbyl group comprising 1 to 12 carbon atoms.
  • hydrocarbyl group means a functional group based on the removal of one hydrogen atom from a hydrocarbon.
  • hydrocarbyl group also means a functional group that consists of carbons and hydrogens.
  • hydrocarbyl group comprising 1 to 12 carbons includes saturated hydrocarbyl groups, monounsaturated hydrocarbyl groups, diunsaturated hydrocarbyl groups, triunsaturated hydrocarbyl groups, polyunsaturated hydrocarbyl groups, aryl hydrocarbyl groups, cycloalkyl group.
  • hydrocarbyl groups examples include alkyl groups, including -CH 3 , -C 2 H 5 , - C 3 H 7 , -C 4 H 9 , -C 5 H 11 , -C 6 H 13 , -C 7 H 15 , -C 8 H 17 , -C 9 H 19 , -C 10 H 21 , -C 11 H 23 ,-C 12 H 25 , and mixtures thereof.
  • Such a hydrocarbyl group may be linear or branched.
  • hydrocarbyl groups include alkene groups containing one double bond, and cycloalkyl groups. Examples include -C 2 H 3 , -C 3 H 5 , -C 4 H 7 , -C 5 H 9 , -C 6 H 11 , - C 7 H 13 , -C 8 H 15 , -C 9 H 17 , -C 10 H 19 , -C 11 H 21 , and -C 12 H 23 . Such a hydrocarbyl group may be linear or branched.
  • a suitable hydrocarbyl group examples include alkenyl groups containing two double bonds, alkynyl groups containing a triple bond, cycloalkene groups, and dicycloalkyl groups. Examples include -C 2 H, -C 3 H 3 , -C 4 H 5 , -C 5 H 7 , -C 6 H 9 , -C 7 H 11 , -C 8 H 13 , -C 9 H 15 , - C 10 H 17 , -C 11 H 19 , and -C 12 H 21 .
  • a suitable hydrocarbyl group examples include -C 3 H, -C 4 H 3 , -C 5 H 5 , -C 6 H 7 , - C 7 H 9 , -C 8 H 11 , -C 9 H 13 , -C 10 H 15 , -C 11 H 17 , and -C 12 H 19 .
  • a suitable hydrocarbyl group examples include -C 4 H, -C 5 H 3 , - C 6 H 5 , -C 7 H 7 , -C 8 H 9 , -C 9 H 11 , -C 10 H 13 , -C 11 H 15 , and -C 12 H 17 .
  • the hydrocarbyl group is an aliphatic group containing 0 to 3 double bonds. Under one embodiment, the aliphatic group is linear.
  • R a , R b , and R c groups are each independently either an alkanol, or an ester thereof.
  • R a , R b , or R c group is an alkanol
  • said group is -(CH 2 ) g -R e , wherein R e is OH, and g is a number 1 to 3.
  • R a , R b , or R c group is an alkanol
  • said group is -(CH 2 ) 1-3 -OH.
  • alkanol groups include -CH 2 OH, -CH 2 CH 2 OH, and -CH 2 CH 2 CH 2 OH, and mixture thereof.
  • R a , R b , or R c group is an ester of an alkanol
  • said group is -(CH 2 ) g -R e , wherein R e is an alkanoyloxy group containing from 8 to 22 carbon atoms.
  • an alkanoyloxy group containing from 8 to 22 carbon atoms means a group of formula -O-C(O)-C 7-21 , wherein C 7-21 is a hydrocarbyl group.
  • R a , R b , or R c group is an ester of an alkanol, said group is -(CH 2 ) 1-3 -O-C(O)-C 7-21 ., wherein C 7-21 is a hydrocarbyl group.
  • the hydrocarbyl portion of the alkanoyloxy group may be fully saturated chain, a monounsaturated chain, diunsaturated chain, or a polyunsaturated chain.
  • Esterquats may be prepared by a reaction of a carboxylic acid with a tertiary alkanolamine followed by a reaction with an alkylating agent. In the presence of a catalyst, tertiary alkanolamine and fatty acid are heated up to temperatures of 250 °C to obtain a high conversion and water removal. The reaction times vary from a few hours to over 10 hours, depending on the reaction conditions and the reactivity of the components. The esteramine is reacted with alkylating agent like dimethyl sulfate or methyl chloride to obtain the corresponding quaternary ammonium compound, or an esterquat. The resulting esterquat has one alkyl group and three alkanol or esterfied alkanol groups.
  • a monoesterquat is a quaternary ammonium compound of formula [R a R b R c R d N + ][X - ], wherein R a is -(CH 2 ) g -R e , wherein R e is an alkanoyloxy group containing from 8 to 22 carbon atoms; R b and R c are each-(CH 2 ) g -OH; R d is a hydrocarbyl group comprising 1 to 12 carbon atoms; g is independently a number from 1 to 3; and X - is a softener compatible anion.
  • a diesterquat is a quaternary ammonium compound of formula [R a R b R c R d N + ][X - ], wherein R a and R b are each independently -(CH 2 ) g -R e , wherein R e is an alkanoyloxy group containing from 8 to 22 carbon atoms; R c is -(CH 2 ) g -OH; R d is a hydrocarbyl group comprising 1 to 12 carbon atoms; g is independently a number from 1 to 3; and X - is a softener compatible anion.
  • a triesterquat is a quaternary ammonium compound of formula [R a R b R c R d N + ][X - ], wherein R a , R b and R c are each independently -(CH 2 ) g -R e , wherein R e is an alkanoyloxy group containing from 8 to 22 carbon atoms; R d is a hydrocarbyl group comprising 1 to 12 carbon atoms; g is a number from 1 to 3; and X - is a softener compatible anion.
  • the esterquat is a mixture of esterquats.
  • the mixture of esterquats is a mixture of monoesterquats.
  • the mixture of esterquats is a mixture of diesterquats.
  • the mixture of esterquats is a mixture of triesterquats.
  • the mixture of esterquats is a mixture of a monoesterquat and a diesterquat. Under one embodiment, the mixture of esterquats is a mixture of a monoesterquat and a triesterquat. Under one embodiment, the mixture of esterquats is a mixture of a diesterquat and a triesterquat. Under one embodiment, the mixture of esterquats is a mixture of a monoesterquat, a diesterquat and a triesterquat. Under one embodiment, the mixture of esterquats is a mixture of a monoesterquat and diesterquats.
  • the mixture of esterquats is a mixture of monoesterquats and a diesterquat. Under one embodiment, the mixture of esterquats is a mixture of monoesterquats and diesterquats. Under one embodiment, the mixture of esterquats is a mixture of a monoesterquat and triesterquats. Under one embodiment, the mixture of esterquats is a mixture of monoesterquats and a triesterquat. Under one embodiment, the mixture of esterquats is a mixture of monoesterquats and triesterquats. Under one embodiment, the mixture of esterquats is a mixture of a diesterquat and triesterquats. Under one embodiment, the mixture of esterquats is a mixture of diesterquats and a triesterquat. Under one embodiment, the mixture of esterquats is a mixture of diesterquats and a triesterquat. Under one embodiment, the mixture of ester
  • the mixture of esterquats is a mixture of a monoesterquat, a diesterquat and triesterquats.
  • the mixture of esterquats is a mixture of a monoesterquat, diesterquats and a triesterquat.
  • the mixture of esterquats is a mixture of a monoesterquat, diesterquats and triesterquats.
  • the mixture of esterquats is a mixture of monoesterquats, a diesterquat and a triesterquat.
  • the mixture of esterquats is a mixture of monoesterquats, a diesterquat and triesterquats.
  • the mixture of esterquats is a mixture of monoesterquats, diesterquats and a triesterquat.
  • the mixture of esterquats is a mixture of monoesterquats, diesterquats and triesterquats.
  • the present invention is directed to a fabric conditioner composition
  • a fabric conditioner composition comprising an esterquat, and a carbodiimide.
  • an esterquat may be a mixture of esterquats is a mixture of monoesterquats, diesterquats and triesterquats. Under one embodiment the weight percent of the monoesterquats, diesterquats and triesterquats are equal to each other.
  • the esterquat comprises about 5 wt% to about 15 wt% of monoesterquats, about 5 wt% to about 15 wt% of diesterquats, and about 75 wt% to about 85 wt% of triesterquats. Under one embodiment, the esterquat comprises about 15 wt% to about 25 wt% of monoesterquats, about 5 wt% to about 15 wt% of diesterquats, and about 65 wt% to about 75 wt% of triesterquats.
  • the esterquat comprises about 25 wt% to about 35 wt% of monoesterquats, about 5 wt% to about 15 wt% of diesterquats, and about 55 wt% to about 65 wt% of triesterquats. Under one embodiment, the esterquat comprises about 35 wt% to about 45 wt% of monoesterquats, about 5 wt% to about 15 wt% of diesterquats, and about 45 wt% to about 55 wt% of triesterquats.
  • the esterquat comprises about 45 wt% to about 55 wt% of monoesterquats, about 5 wt% to about 15 wt% of diesterquats, and about 35 wt% to about 45 wt% of triesterquats. Under one embodiment, the esterquat comprises about 55 wt% to about 65 wt% of monoesterquats, about 5 wt% to about 15 wt% of diesterquats, and about 25 wt% to about 35 wt% of triesterquats.
  • the esterquat comprises about 65 wt% to about 75 wt% of monoesterquats, about 5 wt% to about 15 wt% of diesterquats, and about 15 wt% to about 25 wt% of triesterquats. Under one embodiment, the esterquat comprises about 75 wt% to about 85 wt% of monoesterquats, about 5 wt% to about 15 wt% of diesterquats, and about 5 wt% to about 15 wt% of triesterquats.
  • the esterquat comprises about 5 wt% to about 15 wt% of monoesterquats, about 15 wt% to about 25 wt% of diesterquats, and about 65 wt% to about 75 wt% of triesterquats. Under one embodiment, the esterquat comprises about 15 wt% to about 25 wt% of monoesterquats, about 15 wt% to about 25 wt% of diesterquats, and about 55 wt% to about 65 wt% of triesterquats.
  • the esterquat comprises about 25 wt% to about 35 wt% of monoesterquats, about 15 wt% to about 25 wt% of diesterquats, and about 45 wt% to about 55 wt% of triesterquats. Under one embodiment, the esterquat comprises about 35 wt% to about 45 wt% of monoesterquats, about 15 wt% to about 25 wt% of diesterquats, and about 35 wt% to about 45 wt% of triesterquats.
  • the esterquat comprises about 45 wt% to about 55 wt% of monoesterquats, about 15 wt% to about 25 wt% of diesterquats, and about 25 wt% to about 35 wt% of triesterquats. Under one embodiment, the esterquat comprises about 55 wt% to about 65 wt% of monoesterquats, about 15 wt% to about 25 wt% of diesterquats, and about 15 wt% to about 25 wt% of triesterquats.
  • the esterquat comprises about 65 wt% to about 75 wt% of monoesterquats, about 15 wt% to about 25 wt% of diesterquats, and about 5 wt% to about 15 wt% of triesterquats. Under one embodiment, the esterquat comprises about 5 wt% to about 15 wt% of monoesterquats, about 25 wt% to about 35 wt% of diesterquats, and about 55 wt% to about 65 wt% of triesterquats.
  • the esterquat comprises about 15 wt% to about 25 wt% of monoesterquats, about 25 wt% to about 35 wt% of diesterquats, and about 45 wt% to about 55 wt% of triesterquats. Under one embodiment, the esterquat comprises about 25 wt% to about 35 wt% of monoesterquats, about 25 wt% to about 35 wt% of diesterquats, and about 35 wt% to about 45 wt% of triesterquats.
  • the esterquat comprises about 35 wt% to about 45 wt% of monoesterquats, about 25 wt% to about 35 wt% of diesterquats, and about 25 wt% to about 35 wt% of triesterquats. Under one embodiment, the esterquat comprises about 45 wt% to about 55 wt% of monoesterquats, about 25 wt% to about 35 wt% of diesterquats, and about 15 wt% to about 25 wt% of triesterquats.
  • the esterquat comprises about 55 wt% to about 65 wt% of monoesterquats, about 25 wt% to about 35 wt% of diesterquats, and about 5 wt% to about 15 wt% of triesterquats. Under one embodiment, the esterquat comprises about 5 wt% to about 15 wt% of monoesterquats, about 35 wt% to about 45 wt% of diesterquats, and about 45 wt% to about 55 wt% of triesterquats.
  • the esterquat comprises about 15 wt% to about 25 wt% of monoesterquats, about 35 wt% to about 45 wt% of diesterquats, and about 35 wt% to about 45 wt% of triesterquats. Under one embodiment, the esterquat comprises about 25 wt% to about 35 wt% of monoesterquats, about 35 wt% to about 45 wt% of diesterquats, and about 25 wt% to about 35 wt% of triesterquats.
  • the esterquat comprises about 35 wt% to about 45 wt% of monoesterquats, about 35 wt% to about 45 wt% of diesterquats, and about 15 wt% to about 25 wt% of triesterquats.
  • the esterquat comprises about 45 wt% to about 55 wt% of monoesterquats, about 35 wt% to about 45 wt% of diesterquats, and about 5 wt% to about 15 wt% of triesterquats.
  • the esterquat comprises about 5 wt% to about 15 wt% of monoesterquats , about 45 wt% to about 55 wt% of diesterquats , and about 35 wt% to about 45 wt% of triesterquats .
  • the esterquat comprises about 15 wt% to about 25 wt% of monoesterquats , about 45 wt% to about 55 wt% of diesterquats , and about 25 wt% to about 35 wt% of triesterquats .
  • the esterquat comprises about 25 wt% to about 35 wt% of monoesterquats , about 45 wt% to about 55 wt% of diesterquats , and about 15 wt% to about 25 wt% of triesterquats.
  • the esterquat comprises about 35 wt% to about 45 wt% of monoesterquats, about 45 wt% to about 55 wt% of diesterquats, and about 5 wt% to about 15 wt% of triesterquats.
  • the esterquat comprises about 5 wt% to about 15 wt% of monoesterquats, about 55 wt% to about 65 wt% of diesterquats, and about 25 wt% to about 35 wt% of triesterquats. Under one embodiment, the esterquat comprises about 15 wt% to about 25 wt% of monoesterquats, about 55 wt% to about 65 wt% of diesterquats, and about 15 wt% to about 25 wt% of triesterquats.
  • the esterquat comprises about 25 wt% to about 35 wt% of monoesterquats, about 55 wt% to about 65 wt% of diesterquats, and about 5 wt% to about 15 wt% of triesterquats. Under one embodiment, the esterquat comprises about 5 wt% to about 15 wt% of monoesterquats, about 65 wt% to about 75 wt% of diesterquats, and about 15 wt% to about 25 wt% of triesterquats.
  • the esterquat comprises about 15 wt% to about 25 wt% of monoesterquats, about 65 wt% to about 75 wt% of diesterquats, and about 5 wt% to about 15 wt% of triesterquats. Under one embodiment, the esterquat comprises about 5 wt% to about 15 wt% of monoesterquats, about 75 wt% to about 85 wt% of diesterquats, and about 5 wt% to about 15 wt% of triesterquats.
  • the esterquat is a mixture of about 20 wt% to about 40 wt% of monoesterquat, about 50 wt% to about 65 wt% of diesterquat, and about 10 wt% to about 25 wt% triesterquat.
  • softener compatible anions include chloride, bromide, methylsulfate, ethylsulfate, sulfate, phosphate, or nitrate, formate, lactate, benzoate, and mixtures thereof.
  • the esterquat may be present in any suitable amount. Under one embodiment, the esterquat is present in an amount of about 0.5 wt% to about 20 wt% of the fabric conditioner composition. In one embodiment, the esterquat is present in an amount of about 1.0 wt% to about 20 wt% of the fabric conditioner composition. In one embodiment, the esterquat is present in an amount of about 1.0 wt% to about 15 wt% of the fabric conditioner composition. In one embodiment, the esterquat is present in an amount of about 1.0 wt% to about 10 wt% of the fabric conditioner composition.
  • esterquat is a quaternary ammonium compound that comprises two long (C 16-18 ) fatty acid chains with two weak ester linkages.
  • esterquat is a quaternary ammonium compound of formula [R 1 R 2 R 3 N + -(CH 2 ) q -O-CO-R 4 ][X-], wherein R 4 is an aliphatic hydrocarbyl group comprising 8 to 22 carbon atoms; R 2 and R 3 are each independently -(CH 2 ) s -R 5 , wherein R 5 is an alkoxy carbonyl group containing from 8 to 22 carbon atoms, benzyl, phenyl, C 1-4 alkyl substituted phenyl, OH, or H; R 1 is -(CH 2 ) t -R 6 , wherein R 6 is benzyl, phenyl, C 1-4 alkyl substituted phenyl, OH, or H; q, s, and t
  • the percentages, by weight, of mono, di, and tri esterquats, as described above are determined by the quantitative analytical method described by A. J. Wilkes, C. Jacobs, G. Walraven and J. M. Talbot in "Characterisation of Quaternized Triethanolamine Esters (esterquats) by HPLC, HRCGC and NMR" 4th World Surfactants Congress, Barcelona, vol. 2, 3-7 June 1996, page 389-402 .
  • the percentages, by weight, of the mono, di and tri esterquats measured on dried samples are normalized on the basis of 100%. The normalization is required due to the presence of 10% to 15%, by weight, of non-quaternized species, such as ester amines and free fatty acids.
  • the normalized weight percentages refer to the pure esterquat component of the raw material.
  • the weight % is based on the total amount of monoesterquat, diesterquat, and triesterquat in the composition.
  • the percentage of saturated fatty acids based on the total weight of fatty acids is about 45 % to about 75%. Esterquat compositions using this percentage of saturated fatty acids do not suffer from the processing drawbacks of 100% saturated materials. When used in fabric softening, the compositions provide good consumer perceived fabric softness while retaining good fragrance delivery.
  • the amount is at least 50, 55, 60, 65 or 70 up to 75%. In other embodiments, the amount is no more than 70, 65, 60, 55, or 50 down to 45%. In other embodiments, the amount is 50 to 70%, 55 to 65%, or 57.5 to 67.5%. In one embodiment, the percentage of the fatty acid chains that are saturated is about 62.5% by weight of the fatty acid. In this embodiment, this can be obtained from a 50:50 ratio of hard:soft fatty acid.
  • a ratio of hard fatty acid to soft fatty acid is 70:30 to 40:60. In other embodiments, the ratio is 60:40 to 40:60 or 55:45 to 45:55.
  • the ratio is about 50:50. Because in these specific embodiments, each of the hard fatty acid and soft fatty acid cover ranges for different levels of saturation (hydrogenation), the actual percentage of fatty acids that are fully saturated can vary. In certain embodiments, soft tallow contains approximately 47% saturated chains by weight.
  • the percentage of saturated fatty acids can be achieved by using a mixture of fatty acids to make the esterquat, or the percentage can be achieved by blending esterquats with different amounts of saturated fatty acids.
  • the fatty acids can be any fatty acid that is used for manufacturing esterquats for fabric softening.
  • fatty acids include, but are not limited to, coconut oil, palm oil, tallow, rape oil, fish oil, or chemically synthesized fatty acids.
  • the fatty acid is tallow.
  • esterquat can be provided in solid form, it is usually present in a solvent in liquid form. In solid form, the esterquat can be delivered from a dryer sheet in the laundry. In certain embodiments, the solvent comprises water.
  • the esterquat is typically produced by reacting fatty acid methyl ester with alkanol amine followed by quaternization with dimethyl sulfate.
  • the alkanol amine comprises triethanol amine.
  • the fatty acids can be any fatty acid that is used for manufacturing esterquats for fabric softening.
  • the fatty acid may comprises any fatty acid having from 12 to 22 carbon atoms, typically from 16 to 18 carbon atoms. Examples of fatty acids include, but am not limited to coconut oil, palm oil, tallow, rape oil, fish oil, or chemically synthesized fatty acids.
  • the fatty acid is tallow.
  • the present invention is directed to a fabric conditioner composition
  • a fabric conditioner composition comprising an esterquat, a carbodiimide as defined in the claims, and optionally, additional ingredients.
  • ingredients include fragrances, surfactants, thickening polymers, colorants, clays, buffers, chelating compounds, silicones, fatty alcohols, and fatty esters.
  • the composition can be provided as a fragrance free composition, or it can contain a fragrance.
  • the amount of fragrance can be any desired amount depending on the preference of the user. In certain embodiments, the total amount of fragrance oil is 0.3 to 3 weight % of the composition.
  • the fragrance can be in free form, encapsulated, or both.
  • Fragrance refers to odoriferous materials that are able to provide a desirable fragrance to fabrics, and encompasses conventional materials commonly used in detergent compositions to provide a pleasing fragrance and/or to counteract a malodor.
  • the fragrances are generally in the liquid state at ambient temperature, although solid fragrances can also be used.
  • Fragrance materials include, but are not limited to, such materials as aldehydes, ketones, esters and the like that are conventionally employed to impart a pleasing fragrance to laundry compositions. Naturally occurring plant and animal oils are also commonly used as components of fragrances.
  • the fabric conditioner composition of the present invention may additionally contain a thickener.
  • the thickening polymer is the FLOSOFT TM DP200 polymer (available from SNF Floerger, Andrézieux, France).
  • FLOSOFT TM DP200 is a water soluble cross-linked cationic polymer derived from the polymerization of from 5 to 100 mole percent of cationic vinyl addition monomer, from 0 to 95 mole percent of acrylamide, and from 70 to 300 ppm of a difunctional vinyl addition monomer cross-linking agent.
  • the most preferred thickener is a cross-linked copolymer of a quaternary ammonium acrylate or methacrylate in combination with an acrylamide comonomer.
  • the thickener in accordance provides fabric softening compositions showing long term stability upon storage and allows the presence of relatively high levels of electrolytes without affecting the composition stability. Besides, the fabric softening compositions remain stable when shear is applied thereto.
  • the amount of this thickening polymer is at least 0.001 weight %. In other embodiments, the amount is 0.001 to 0.35 weight %.
  • Suitable amino carboxylic acid compounds include: ethylenediamine tetraacetic acid (EDTA); N-hydroxyethylenediamine triacetic acid; nitrilotriacetic acid (NTA); and diethylenetriamine pentaacetic acid (DTPA).
  • Suitable organo aminophosphonic acid compounds include: ethylenediamine tetrakis (methylenephosphonic acid); 1-hydroxyethane 1,1-diphosphonic acid (HEDP); and aminotri (methylenephosphonic acid).
  • the composition can include amino tri methylene phosphonic acid, which is available as Dequest TM 2000 from Monsanto (Creve Coeur, Missouri, USA).
  • the composition can include glutamic acid, N,N-diacetic acid, tetra sodium salt, which is available as Dissolvine TM GL from AkzoNobel (Amsterdam, Netherlands).
  • the fabric conditioner composition includes a C 13-15 fatty alcohol EO 20:1, which is a nonionic surfactant with an average of 20 ethoxylate groups.
  • the amount is 0.05 to 0.5 weight %.
  • the fabric conditioner composition comprises cetyl trimethyl ammonium chloride.
  • cetyl trimethyl ammonium chloride is present in an amount of 0.001 to 5 weight %.
  • the cetyl trimethyl ammonium chloride in combination with the branched amine functional silicone reduces foam generation during laundering, which reduces the amount of rinsing needed.
  • Samples 1 to 3 fabric conditioner compositions based on triethanol amine tallow fatty acid triesterquat are prepared. For each of Samples 1 to 3, a first volume of deionized water was provided at a given temperature. A quaternary cationic surfactant, comprising an aqueous solution of a mono-hexadecyl quaternary ammonium cationic surfactant having 60 wt % active content, was added to the water in an amount so as to comprise 0.37 wt % of the final composition. The resultant mixture was mixed using a high shear mixer.
  • Esterquat HS90 (available from Stepan Company, Northfield, Illinois, USA) was added in an amount as to comprise 4.5 wt% of the final composition.
  • True Love E fragrance and triclosan were added in amounts as to comprise 0.6 wt% and 0.03 wt% of the final composition.
  • Carbodilite V02 a waterborne polycarbodiimide resin with hydrophilic segments, available from Nisshinbo Chemical Inc. (Ch -ku, Tokyo, Japan), was added in an amount as to comprise 0.3 wt% of the final composition to Sample 2.
  • Carbodilite SV02 a waterborne polycarbodiimide resin with hydrophilic segments, available from Nisshinbo Chemical Inc., was added in an amount as to comprise 0.3 wt% of the final composition to Sample 3.
  • No polycarbodiimide was added to the comparative formulation of Sample 1.
  • Sufficient amount of hydrochloric acid was added to the compositions of Samples 2 and 3 to lower the pH from above 8 to a pH of 3.
  • Triesterquat drop and monoesterquat drops were determined by measuring the level of triesterqu+at and monoesterquat before and after aging. Aging was performed by leaving the samples at 50 °C for 4 weeks. The determination of the esterquat levels was performed by using procedures adopted from " Characterisation of Quaternized Triethanolamine Esters (Esterquats) by HPLC, HRCGC and NMR" A. J. Wilkes, C. Jacobs, G.Walraven and J. M. Talbot, Colgate Palmolive R&D Inc., Proceeding Fourth World Surfactants Congress, Barcelona, Vol. 2, 3-7 June 1996, page 389-402 .
  • Table 1 Sample V02 SV02 Viscosity (cP) Zeta-potential (mV) DSC ⁇ H (J/g) Triester drop (molar %) Monoester drop (molar %) 1* 15.6 279.2 0.61 1.1 7.0 2 0.3 wt% 22.8 208.5 0.47 1.1 4.4 3 0.3 wt% 17.6 266.6 0.62 1.0 4.0 *: comparative composition

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Claims (8)

  1. Textilpflegezusammensetzung, umfassend:
    (a) ein Esterquat, und
    (b) ein Carbodiimid;
    wobei das Esterquat eine quaternäre Ammoniumverbindung der Formel ist:

            [R1R2R3N+-(CH2)q-O-CO-R4][X-]

    worin:
    R4 eine aliphatische Hydrocarbylgruppe mit 8 bis 22 Kohlenstoffatomen ist;
    R2 und R3 sind jeweils unabhängig voneinander -(CH2)s-R5
    R5 ist eine Alkoxycarbonylgruppe mit 8 bis 22 Kohlenstoffatomen, Benzyl, Phenyl, C1-4-alkylsubstituiertes Phenyl, OH oder H;
    R1 ist -(CH2)t-R6;
    R6 ist Benzyl, Phenyl, C1-4-alkylsubstituiertes Phenyl, OH oder H;
    q, s und t sind jeweils unabhängig voneinander eine Zahl von 1 bis 3; und
    X(-) ein weichmacherverträgliches Anion ist.
  2. Textilpflegezusammensetzung nach Anspruch 1, wobei das Carbodiimid eine Verbindung der Formel ist:

            R-N=C=N-R'

    worin:
    R und R' jeweils unabhängig voneinander C1-6-Alkyl, Aryl, Cycloalkyl oder -(CH2)xNRmRn sind, wobei
    x eine Zahl von 1 bis 5 ist; und
    Rm und Rn jeweils unabhängig voneinander H oder C1-6-Alkyl sind.
  3. Textilpflegezusammensetzung nach Anspruch 1 oder Anspruch 2, wobei das Carbodiimid ausgewählt ist aus der Gruppe bestehend aus N,N'-Dicyclohexylcarbodiimid, N,N'-Diisopropylcarbodiimid, N,N'-Diphenylcarbodiimid, N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimid, N-Ethyl-N'-(3-dimethylaminopropyl)carbodiimid, 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimidmethiodid, N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimid und Mischungen davon.
  4. Textilpflegezusammensetzung nach Anspruch 1 oder Anspruch 2, wobei das Carbodiimid 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimid ist.
  5. Textilpflegezusammensetzung nach Anspruch 1, wobei die Hydrocarbylgruppe eine aliphatische Gruppe ist, die 0 bis 3 Doppelbindungen enthält.
  6. Textilpflegemittel nach Anspruch 1 oder Anspruch 5, wobei die aliphatische Gruppe linear ist.
  7. Textilpflegezusammensetzung nach einem der vorangehenden Ansprüche, wobei die Textilpflegezusammensetzung ferner ein kationisches Tensid umfasst.
  8. Textilpflegezusammensetzung nach einem der vorstehenden Ansprüche, wobei das Esterquat ein Gemisch aus 20 Gew.-% bis 40 Gew.-% Monoesterquat, 50 Gew.-% bis 65 Gew.-% Diesterquat und 10 Gew.-% bis 25 Gew.-% Triesterquat ist.
EP18837087.8A 2018-12-27 2018-12-27 Zusammensetzungen zur häuslichen pflege Active EP3884019B1 (de)

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CN (1) CN113227340A (de)
AU (1) AU2018455779B2 (de)
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Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3915867A (en) 1973-04-24 1975-10-28 Stepan Chemical Co Domestic laundry fabric softener
GB9613758D0 (en) * 1996-07-01 1996-09-04 Unilever Plc Detergent composition
EP2188358B1 (de) * 2007-09-08 2011-04-06 Unilever PLC Verbesserungen im zusammenhang mit wäscheweichmachern
US9758927B2 (en) * 2011-09-01 2017-09-12 Colgate-Palmolive Company Method for ease of ironing
EP3342395B1 (de) * 2015-08-27 2024-08-07 LG Household & Health Care Ltd. Zusammensetzung zur haaroberflächenmodifikation

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CN113227340A (zh) 2021-08-06
AU2018455779A1 (en) 2021-07-01
AU2018455779B2 (en) 2022-05-26
EP3884019A1 (de) 2021-09-29

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