WO2000006678A1 - Compositions utiles comme agents adoucissants ou nettoyants et pour les soins d'hygiene - Google Patents

Compositions utiles comme agents adoucissants ou nettoyants et pour les soins d'hygiene Download PDF

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Publication number
WO2000006678A1
WO2000006678A1 PCT/US1999/016981 US9916981W WO0006678A1 WO 2000006678 A1 WO2000006678 A1 WO 2000006678A1 US 9916981 W US9916981 W US 9916981W WO 0006678 A1 WO0006678 A1 WO 0006678A1
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Prior art keywords
reaction mixture
alkanolamine
percent
alkyl group
formula
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PCT/US1999/016981
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English (en)
Inventor
Pierre Lenoir
Kees Delcour
Marinus Meertens
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The Dow Chemical Company
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Publication date
Application filed by The Dow Chemical Company filed Critical The Dow Chemical Company
Priority to EP99937527A priority Critical patent/EP1102833A1/fr
Priority to CA002338906A priority patent/CA2338906A1/fr
Priority to AU52341/99A priority patent/AU5234199A/en
Publication of WO2000006678A1 publication Critical patent/WO2000006678A1/fr

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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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/42—Amino alcohols or amino ethers
    • 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
    • C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
    • 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
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/22—Agents rendering paper porous, absorbent or bulky
    • D21H21/24—Surfactants

Definitions

  • the present invention relates to a process for manipulating esterification reactions of alkanolamines to favor the formation of either the monoester or diester at the expense of the formation of higher esters.
  • This process produces heretofore unknown reaction mixtures which can be advantageously used in laundry, cleaner, or personal care applications.
  • the present invention relates to alkoxylated ester-amine compositions, the protonated or quatemized forms thereof, and processes for the preparation of the same.
  • esterquats are known as cationic fabric softening agents. See, for example, WO-A-93/25648, DE-A-4,339,643 and US-A-4,339,391 ; US-A-4,767,547, US- A-4,874,554 and US-A-5,066,414.
  • Other examples of known quatemized ester-amines include US-A-5,463,094, which discloses quaternary ammonium compounds which the starting tertiary amine can include carboxylic esters of hydroxyalkyl groups.
  • 97 105 620.5 teaches a family of esterified alkanolamines prepared by first alkoxylating an alkanolamine having from 1 to 3 OH groups with alkylene oxides having from 2 to 6 carbons, then esterifying the compounds.
  • 97/42279 to make such compositions requires the use of 1.6 to 1.8 moles of unsaturated fatty acids per mole of trialkanol amine.
  • the unsaturated fatty acid is required to have a high level of the cis isomer, or an isomerizing step to convert esters to the desired cis/trans configuration.
  • This reference also teaches a controlled heating protocol which is necessary in order to achieve the desired goal of high diester.
  • DE-A-4,243,701 discloses that beneficial fabric softening properties can be seen from the diesterquat of triethanolamine (TEA), but this reference provides no method for obtaining such diesters in a reaction mixture.
  • WO-A-97/03160 indicates the benefits of having cationic ester surfactants in laundry detergents. These benefits include superior greasy cleaning and improved antiredeposition of soils during the wash process.
  • CET cationic ester surfactants
  • Reaction mixtures made according to the present invention exhibit improved softening or detergency properties and are more hydrolytically stable than reaction mixtures of the prior art. This makes them well-suited for use in fabric softeners, paper softeners, cleaners, detergents, and personal care applications.
  • a lower alkanolamine i.e. a primary or secondary amine
  • a lower alkanolamine is alkoxylated with an alkylene oxide or a mixture of alkylene oxides, then esterified with a carboxylic acid, and then optionally neutralized or quatemized.
  • the alkanolamines suitable as the starting material for this embodiment of the invention have the structure: ( C R ' R 2 ) n - C R 3 R 4 0 H
  • R 1 , R 2 , R 3 and R 4 are independently in each moiety H or an alkyl group; n is independently in each moiety a number equal to 1 or greater; R 1 , R 2 , R 3 , R 4 and n are such that the number of carbon atoms between N and O is no more than 18; R 7 is H or R 5 ; and R 5 is (CR 1 R 2 ) n -CR 3 R 4 -OH, an alkyl having from 1-6 carbon atoms, a cycloalkyl having 6 carbon atoms, or an aryl group.
  • the alkylene oxides suitable for use in the present invention correspond to the formula C y H 2y O, where y is from 2 to 18, preferably 2 to 6.
  • the materials are chosen such that if y is only 2 then for at least some of the lower alkanolamines in the mixture, in at least one moiety on the N group, R 3 or R 4 will be an alkyl group.
  • a reaction mixture is prepared which has a higher proportion of diester or monoester, at the expense of the completely esterified alkanolamine, than previously reported.
  • the process of the invention can produce reaction mixtures having greater than 50 percent by weight of the diester component.
  • the monoester portion in the final reaction mixture can represent 60 percent or more by weight of the total reaction mixture.
  • compositions of the present invention exhibit surprisingly high hydrolytic stability over a wide pH range, have unexpectedly low melting points, are more compatible with detergent and personal care ingredients and they can be more easily handled either in the diluted form or formulated as stable liquid concentrates as compared to corresponding reaction mixtures made from di- or tri-ethanolamines. Accordingly, in another embodiment of the present invention these compounds are used in such applications as fabric softeners, paper softeners, detergents, cleaners and personal care items.
  • the composition of the present invention comprises a reaction mixture comprising monoester (II), diester (III), triester (IV) and optionally free alkanolamine (I) components corresponding to the following formulae:
  • R is an alkyl group having 1 to 30 carbons
  • R 1 , R 2 , R 3 and R 4 are independently in each moiety H or an alkyl group provided that R 3 and R 4 are not all H in all of the moieties;
  • n is independently in each moiety a number equal to 1 or greater;
  • n and R 1 , R 2 , R 3 and R 4 are such that the number of carbon atoms between N and O is no more than 18;
  • R 5 is (CR 1 R 2 ) n -CR 3 R 4 -OH, an alkyl having from 1 -6 carbon atoms, a cycloalkyl having 6 carbon atoms, or an aryl group;
  • Q is H, an alkyl group having 1 to 6 carbons, or an aryl group having 6-12 carbons, optionally substituted with an alkyl group, or HOCHR 6 CH 2 -, wherein R 6 is H or an alkyl group having 1 to 4 carbons;
  • X is an inorganic or organic acid anion;
  • reaction mixture having been prepared at least in part from the esterification of an alkanolamine corresponding to the formula:
  • composition of the present invention comprises a reaction mixture comprising monoester (II), diester (III), triester (IV) and, optionally, free alkanolamine (I) components corresponding to the following formulae:
  • R is an alkyl group having 1 to 30 carbons
  • R ⁇ R 2 , R 3 and R 4 are independently in each moiety H or an alkyl group provided that R 3 and R 4 are not all H in all of the moieties in the reaction mixture;
  • n is independently in each moiety a number equal to 1 or greater;
  • n and R 1 , R 2 , R 3 and R 4 are such that the number of carbon atoms between N and O is no more than 18;
  • R 5 is (CR R 2 ) n -CR 3 R 4 -OH, an alkyl having from 1-6 carbon atoms, a cycloalkyl having 6 carbon atoms, or an aryl group;
  • Q is H, an alkyl group having 1 to 6 carbons, or an aryl group having 6-12 carbons, optionally substituted with an alkyl group, or HOCHR ⁇ CH 2 -, wherein R 6 is H or an alkyl group having 1 to 4 carbons;
  • X is an inorganic or organic acid anion
  • p is from O to l ,
  • reaction mixture having been prepared at least in part from the esterification of an alkanolamine corresponding to the formula:
  • composition includes both a single chemical entity and mixtures of chemical entities which correspond to the same general formula.
  • moiety means a group of inter-connected atoms which is attached to the central nitrogen atom.
  • R have from 4-24 carbon atoms, and more preferred that R have from 7-22 carbon atoms.
  • the R group may be straight or branched, and may have different levels of saturation. Generally, it is preferred that the R group have an Iodine value less than 140. Iodine values can be calculated by ways known in the art. For some applications, such as concentrated fabric softeners or clear transparent formulations, it is generally preferred that the R group have Iodine values greater than 20, but in other applications, such as detergents, Iodine values less than 20, including fully saturated R groups can be advantageously used. For general, less concentrated fabric softener use, the Iodine values have not been shown to have a significant effect and so all ranges may be used.
  • n be equal to 1 , especially in those moieties where R 3 or R 4 is an alkyl group. It is also preferred that R 1 and R 2 are H. It is also generally preferred that not both R 3 and R 4 are alkyl groups in the same moiety. Furthermore it is preferred that when R 3 or R 4 is an alkyl group, it is an alkyl group having 1 or 2 carbons. It is also preferred that n and R 1 , R 2 , R 3 and R 4 are such that the number of carbon atoms between N and O is no more than 6.
  • p represents an average, showing the degree of neutralization or quatemization, but that for any particular molecule, it will be 0 or 1. It is also within the scope of this invention to not quaternize the reaction mixture at all, although this is not preferred.
  • the invention comprises a procedure to make esterified alkanolamines, wherein the reaction mixture will have a disproportionate amount of not fully esterified product than would normally be expected.
  • the procedure comprises esterifying an alkanolamine (or mixtures thereof) corresponding to the following formula:
  • n is independently in each moiety a number equal to 1 or greater;
  • n and R 1 , R 2 , R 3 and R 4 are such that the number of carbon atoms between N and O is no more than 18;
  • R 5 is (CR 1 R 2 ) n -CR 3 R 4 -OH, an alkyl having from 1-6 carbon atoms, a cycloalkyl having 6 carbon atoms, or an aryl group.
  • the alkanolamine is formed by alkoxylating a primary or secondary alkanolamine (or mixtures thereof) with one or more alkylene oxides where the primary or secondary alkanolamine corresponds to the formula:
  • R 1 , R 2 , R 3 and R 4 are independently in each moiety H or an alkyl group; n is independently in each moiety a number equal to 1 or greater; n, R 1 , R 2 , R 3 and R 4 are such that the number of carbon atoms between N and O is no more than 18; R 7 is H or R 5 ; and R 5 is (CR , R 2 ) n -CR 3 R 4 -OH, an alkyl having from 1-6 carbon atoms, a cycloalkyl having 6 carbon atoms, or an aryl group; and the alkylene oxide corresponds to the formula C y H 2y O, where y is from 2 to 18, preferably 2 to 6.
  • the materials are chosen such that if y is only 2 then for at least some of the lower alkanolamines in the mixture, in at least one moiety on the N group, R 3 or R 4 will be an alkyl group. It is preferred that n be equal to 1 , especially in those moieties where R 3 or R 4 are an alkyl group. It is also preferred that R 1 and R 2 are H. It is also generally preferred that not both R 3 and R are alkyl groups in the same moiety. Furthermore it is preferred that when R 3 or R 4 is an alkyl group, it is an alkyl group having 1 or 2 carbons. It is also preferred that n and R 1 , R 2 , R 3 and R 4 are such that the number of carbon atoms between N and O is no more than 6.
  • Preferred alkylene oxides include ethylene oxide, propylene oxide and butylene oxide.
  • this alkoxylation reaction process may be carried out in the presence of an alkaline catalyst, such as sodium, potassium, calcium, barium and strontium hydroxide, in an amount of from 0.01 to 5, preferably 0.1 to 0.5, percent by weight based on the total weight of the mixture at the completion of the reaction. Care must be taken when using catalyst not to alkoxylate the OH groups, and so in general, the use of catalyst is not preferred for this invention.
  • an alkaline catalyst such as sodium, potassium, calcium, barium and strontium hydroxide
  • Temperature and pressures are not critical, but conveniently the alkoxylation reaction is carried out at an elevated 5 temperature, preferably at a temperature from 50°C to 200°C, more preferably from 80°C to 120°C and a pressure of from 1 to 80 bars.
  • the alkaline catalysts suitable for use in this reaction are well known to a person skilled in the art. After completion of the reaction, that is, for example, when the pressure does not change any more, the catalyst is removed by a suitable method, such as by filtration over an absorbing clay, 0 for example, magnesium silicate, or neutralized with an inorganic acid such as, for example, hydrochloric acid, or an organic acid such as, for example, acetic acid. If desired, an excess of an acid can be used, so that the excess of the acid can serve as a catalyst in the subsequent reaction step. It is advantageous to carry out the alkoxylation reaction in the presence of a defoaming agent.
  • the esterification reaction comprises contacting the alkanolamine with a carboxylic acid (or a mixture of carboxylic acids) under conditions sufficient to cause at least a portion of the carboxylic acid to react with at least a portion of the OH groups on the alkanolamine so as to form esters.
  • the carboxylic acid corresponds to the formula RCOOH, where R is an alkyl group having 1 to 30 carbons. It is preferred that R have o from 4-24 carbon atoms, and more preferred that R have from 7-22 carbon atoms.
  • R group may be straight or branched, and may have different levels of saturation. Generally, it is preferred that the R group have an Iodine value less than 140. Iodine values can be calculated by ways known in the art. For some applications it is preferred that the R group have Iodine values greater than 20, but in other applications, Iodine 5 values less than 20, including fully saturated R groups can be advantageously used. Where unsaturated R groups are used, it is preferred that the ratio of the cis to trans isomer be 80:20 or greater.
  • carboxylic acids useful in the esterification reaction include valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, and o lignoceric acid, and the branched isomers thereof (isovaleric acid, for example), or the unsaturated isomers thereof (for example, oleic acid).
  • fatty acids are well-known to the person of ordinary skill in the art.
  • the esterification reaction conveniently is carried out at an elevated temperature, preferably at a temperature from 50°C to 250°C, more preferably from 5 180°C to 220°C, and reduced pressure, preferably from 1 to 500 mbar, more preferably from 20 to 200 mbar.
  • elevated temperature preferably at a temperature from 50°C to 250°C, more preferably from 5 180°C to 220°C
  • reduced pressure preferably from 1 to 500 mbar, more preferably from 20 to 200 mbar.
  • the acid be added in an amount of from 0.5 to 0.7 moles of carboxylic acid per mole of OH on the alkanolamine (1.5 to 2.1 moles acid per mole trialkanolamine).
  • reaction mixtures of trialkanolamines with a diester content greater than 50 percent by weight can be observed even when adding the acid at ratios of greater than 1.8 moles of acid per mole of trialkanolamine (0.6 moles of acid per mole equivalent of trialkanolamine) or less than 1.6 moles of acid per mole of trialkanolamine (0.53 moles of acid per mole equivalent of trialkanolamine).
  • reaction mixtures having greater than 55 percent by weight can be obtained. If a monoester of a dialkanol amine is desired, then it is preferred that the acid be added in an amount of from 0.4 to 1.1 moles of acid per mole of dialkanol amine (0.2 to 0.55 moles of acid per mole of OH on the dialkanol amine). At these ratios, reaction mixtures having greater than 60 percent monoester can be obtained.
  • the esterified alkanolamines can then be neutralized or quatemized by contacting the esterified alkanolamines with a composition corresponding to the formula QX, under conditions sufficient to cause at least a portion of the esterified alkanolamines to form a quatemized, or neutralized product.
  • Q in the above formula is H, an alkyl group having 1 to 6 carbons, or an aryl group having 6-12 carbons, optionally substituted with an alkyl group, or HOCHR 6 CH 2 -, wherein R 6 is H or an alkyl group having 1 to 4 carbons; and X is an inorganic or organic acid anion.
  • the neutralization reaction is preferably carried out at the molar ratio of from 0.05 to 2 moles QX per mole of esterified alkanolamine. Such a reaction can be carried out at room temperature or above the melting point of the alkoxylated ester-amine compound, and at a pressure of from 1 to 50 bars.
  • the quatemization reaction is preferably carried out at the ratio of from 0.1 to 20 moles QX per mole of esterified alkanolamine, at a temperature of from 30°C to 150°C, and a pressure of from 1 to 50 bars.
  • Any known inorganic acid such as, for example, hydrochloric acid, or organic acid such as, for example, citric acid can be used as the HX compound to protonate the alkoxylated ester-amine (see for example, WO-A- 94/04641 and WO-A-94/04642).
  • Any known quatemizing agent can be used as the QX compound.
  • Suitable quatemizing agents of formula QX include alkyl halides, dialkyl sulfates, and trialkyl phosphates.
  • Preferred alkyl halides include methyl chloride, ethyl chloride, methyl bromide, and ethyl bromide; preferred dialkyl sulfates include dimethyl sulfate, and diethyl sulfate, and preferred trialkyl phosphates include trimethyl phosphate and triethyl phosphate. It is advantageous to carry out the quatemization reaction in the presence of a defoaming agent. It can also be advantageous to carry out the quatemization reaction in the presence of an additive which can lower the melting point of the reaction mixture, as is known in the art. These additives can be added at any stage of the reaction.
  • Suitable additives include materials such as water, isopropanol, propanediol, dipropylene glycol, PEG, PPG, alkoxylated fatty acids and alcohols having more than 3 carbons in the fatty chain, glycol ether solvents such as DOWANOLTM P and E series, diether solvents such as PROGLYDETM DMM, tetrahydrofuran, methanol, ethanol, hexanediol, and acetone.
  • compositions of the present invention exhibit good softening, detergency, antifoaming and antistatic properties, they have low melting points, and are hydrolytically stable at various pH values.
  • the compositions of the invention which have higher diester content tend to be especially well suited for the fabric and paper softening applications, while those compositions with high monoester content tend to show improved detergency properties.
  • hydrolytically stable means that less than 30 percent, preferably less than 20 percent, of composition of Formulas (l-IV) above when Q is not H and p is greater than 0.75 and less than 40 percent of a composition of Formulas (l-IV) above when p is 0, or Q is H, hydrolyzes after 4 weeks from a 5 percent aqueous solution having a pH value of 4, at a temperature of 50°C.
  • hydrolytically stable means that less than 45 percent, preferably less than 30 percent hydrolyzes after 4 weeks from a 5 percent aqueous solution having a pH value of 4, at a temperature of 50°C, when p is greater than 0.8. It should be understood that the extent of hydrolysis defined above is valid for a value of pH 4 and that hydrolysis extent would decrease with decreasing pH and increase with increasing pH.
  • the improved hydrolytic stability of the compositions of the present invention allow them to be used in liquid or gel detergent, softergent or softener formulations.
  • compositions of the present invention are compatible even with fabric and paper softeners' ingredients and detergents ingredients which are normally not compatible with known softening compounds without the presence of special additives. Due to these properties the composition mixtures of the present invention can be formulated into formulations suitable for various end use applications such as, for example, fabric and paper softening formulations, formulation for cleaning and conditioning fabric materials ("softergents"), antifoaming formulations, personal care formulations, lubricating formulations, drilling fluid formulations and hard surface cleaning formulations.
  • the present invention concerns a fabric softening, paper softening, detergent, personal care, or cleaner formulation comprising the composition of the invention.
  • the formulations of the present invention can also incorporate one or more known ingredients commonly used in fabric softening, paper softening, detergent, personal care or cleaner formulations.
  • the fabric and paper softening formulations of the present invention can be in various forms, such as, for example, aqueous or anhydrous liquid formulations, super concentrate liquid formulations, solid formulations obtained by a suitable process such as grinding the softener composition or depositing it onto solid substrates such as powders or granules, or onto cellulosic substrate sheets for use in tumble dryers.
  • the fabric softening formulations can be used in a tumbler dryer or in the rinse cycle in a washing machine for example by dispensing the fabric softening formulation via a dispensing compartment optionally with dilution prior to dosing into the dispensing compartment.
  • the fabric and paper softening formulations of the present invention which have a pH below 8 when diluted for normal use conditions are preferred. Normal use conditions are known in the art but are generally in the range of from 0.01 to 0.5 percent by weight active ingredient, and most commonly about 0.05 percent.
  • the present invention concerns an anhydrous or aqueous fabric and paper softening formulation comprising at least 0.01 , preferably from 0.01 to 95 percent by weight the composition of the invention.
  • the liquid fabric and paper softening formulations of the present invention may be prepared by mixing the composition of the invention with a liquid carrier and, optionally, at least one other above mentioned ingredient in a standard formulation mixing equipment and in accordance with techniques known to a person skilled in the art. Low-shear mixing is generally sufficient to adequately and uniformly mix the softening composition within the softening formulation.
  • the final softening formulation, whether in concentrated or diluted form must be easily pourable by the end user.
  • the formulation may be formulated to be diluted (for example, for refill packs) by a factor of generally 4:1 or more, preferably up to 8:1 or even up to 20:1.
  • fabric softener formulations contain normally from 5 to 20 percent of softening agent. They are normally opaque milky emulsions of various viscosities. In general the viscosity of fabric softening formulations increase with the increase in concentration of its fabric softening agent. Additives are normally used to stabilize more concentrated fabric softening formulations (for example, those containing between 10 and 20 percent softening agent). It should be noted that WO-A-96/21715 teaches the use of special deflocculating nonionic polymeric surfactants to allow incorporation of up to 35 percent of a softening agent. The absence of additives would lead to gelling of softening formulations containing more than 15 percent of a softener agent.
  • compositions of the present invention which have a high diester content have unexpectedly higher hydrolytic stability than known softening agents, but they also have lower melting points than known softening agents based on esterquats of ethanolamine.
  • this unique combination of high hydrolytic stability and low melting points of the compositions allow for the formulation of stable super-concentrated and, if desired, anhydrous fabric softening formulations with or without the incorporation of stabilizing additives.
  • super concentrated and anhydrous fabric softening formulations incorporating the composition of the invention are transparent in most instances.
  • the present invention also encompasses the super concentrated fabric softening formulations comprising from 10 to 100 percent of the composition of the invention.
  • These super concentrated formulations can be used for example, for a refill pack (to be diluted in a large bottle) or as concentrates for direct use by a consumer, or can help save transportation costs of the softener or the fabric or paper softening formulations.
  • softergents Mixtures of fabric softeners and detergents (softergents) are commercially available. Such formulations can be in liquid, paste or granular form. Such softergents normally contain soft clays and/or cationic surfactants having only one long alkyl group in the molecule (for example, lauryltrimethyl ammonium chloride).
  • Known softergents have a number of limitations. For example, the softening performance of these softergents is inferior to the performance of a fabric softener used separately in the last rinse of the wash process.
  • Another limitation is the difficulty in formulating softergents containing cationic softener having more than one long alkyl chain in the molecule (common softening agent used in softening formulations).
  • Still another limitation is the fact that a cationic softener having one or more ester links must be formulated at a low pH which does not correspond to typical neutral-to-alkaline pH of the detergent.
  • compositions of the present invention due to the compatibility of compositions of the present invention with conventional detergent ingredients and because they are hydrolytically stable at typical detergent pH's they can conveniently be formulated with any known detergent ingredients into a softergent having none of the aforementioned limitations.
  • the present invention concerns a powder or liquid softergent formulation comprising 1 to 90 weight percent of at least one composition of the invention, which softergent formulation has a pH in the range of from 1.5 to 12.
  • the absence of solvent in the composition of the invention makes the softergent safer to use.
  • the composition permits the selection of a softener which has a low enough melting point to be suitable for making powder softergent and allows optimum dispersion during the wash cycle.
  • compositions of the present invention can suitably be formulated with a wide variety of known materials commonly found in fabric or paper softening formulations, laundry detergents, hard surface cleaning formulations and personal care formulations.
  • materials used in fabric or paper softening formulations, laundry detergents, hard surface cleaning formulations and personal care formulations include, but are not limited to the following:
  • Enzymes and Enzyme Stabilizers - Enzymes can be included for various fabric cleaning and fabric softening purposes.
  • suitable enzymes include proteases, amylases, lipases, cellulases, and peroxidases, as well as mixtures thereof.
  • the enzymes may be of any suitable origin, such as vegetable, animal, bactericidal, fungal and yeast origin.
  • the enzymes used may be stabilized by the presence of water-soluble sources of calcium and/or magnesium ions in the finished compositions which provide such ions. Any water-soluble calcium or magnesium salt can be used as a source of calcium or magnesium ions.
  • a wide range of useful enzyme and enzyme stabilizer materials are described in WO-A-95/19951 and WO-A-96/21715, and EP-A-0579295 and EP-A-0583536.
  • Bleaching Agents and Bleach Activators Any known bleaching agent used in fabric or paper treatment applications can be used. Nonlimiting examples of suitable bleaching agents include oxygenated bleaches, percarboxylic acid bleaches, peroxygen bleaches and mixtures thereof. Bleach activator can also be used. Various nonlimiting examples of useful bleaching agents and bleach activators are given in WO- A-95/19951.
  • Builders Inorganic and organic builders commonly used in fabric laundering formulations to assist in removal of paniculate solids can be used. Suitable builders include, but are not limited to, phosphates, polyphosphates, silicates, aluminosilicates, phosphonates, carboxylates, zeolites and succinates. Nonlimiting examples of suitable builders are described in WO-A-95/19951 and EP-A-0579295, and EP-A-0580245.
  • Soil Release Agents Any known polymeric soil release agent used in laundry cleaning formulations can be used.
  • Polymeric soil release agents include, but are not limited to, the compounds having: (i) at least one nonionic hydrophilic component consisting essentially of (a) polyoxyethylene segments with a degree of polymerization of at least 2, or (b) oxypropylene or polyoxypropylene segments with a degree of polymerization of from 2 to 10, or (c) a mixture of oxyalkylene units comprising oxyethylene and from 1 to 30 oxypropylene units, (d) cellulosic derivatives such as hydroxyether cellulosic polymers, (e) copolymeric blocks of terephthalate with polyethylene oxide or polypropylene oxide.
  • Nonlimiting examples of useful soil release agents are given in WO-A-95/04802, WO-A-93/23510 and WO-A-
  • Chelating agents Any known chelating agent is suitable for use. Suitable chelating agents include, but are not limited to, amino carboxylates, amino phosphonates, polyfunctionally-substituted aromatic chelating agents and mixtures thereof. It is believed that the benefit of the chelating materials is due in part to their exceptional ability to remove iron and manganese ions from washing solutions by formation of soluble chelates. Nonlimiting examples of suitable chelating agents are described in WO-A-95/19951 and WO-A-96/21715.
  • Clay Soil Removal/Anti-Redeposition Agents Any water-soluble alkoxylated amines having clay soil removal and anti-redeposition properties normally used in granular or liquid detergents can be used. Nonlimiting examples of useful clay soil removal/anti-redeposition agents are described in WO-A-95/19951.
  • Dispersing Agents - Suitable dispersing agents are polymeric dispersing agents such as, for example, polymeric polycarboxylates and polyethylene glycols, normally used in detergents. Nonlimiting examples of the dispersing agents are given in WO-A-95/19951. Protonated amines, such as those described in WO-A- 93/25648, and terephthalate/alkylene oxide copolymers, such as those described in WO-A-96/21715 can be used to enhance dispersion stability.
  • Optical Brighteners Any known brightener used in detergents can be used. Suitable brighteners include, but are not limited to, derivatives of stilbene, pyrazoline, coumarin, and carboxylic acid. Nonlimiting examples of suitable brighteners are given in WO-A-95/19951 and WO-A-96/21715.
  • Suds Suppressors Any known compound that suppresses or reduces the formation of suds is suitable for use. Such compounds include, but are not limited to, silicones, silica-silicone mixtures, monocarboxylic fatty acids and soluble salts thereof, high molecular weight hydrocarbons such as paraffin, and fatty acid esters of monoalcohols. These and other suitable suds suppressors are described in WO-A- 95/19951 and EP-A-0579295.
  • Fabric Softeners Any known fabric softener compound can be used.
  • suitable fabric softener compounds include clay softeners, conventional quaternary ammonium softening agents, anionic softeners, nonionic softeners, and cationic softeners. These and other suitable fabric softeners are described in WO-A-95/04802, WO-A-95/19951 , and WO-A-96/21715, and EP-A-0580245.
  • (k) Detersive Surfactants Various surfactant materials such as anionic, nonionic, cationic, ampholytic, and zwitterionic surfactants can be used.
  • suitable surfactant include linear alkyl sulfonates ("LAS"), C Montgomery- C 18 alkyl benzene sulfonates, primary and secondary branched-chain and random C 10 - C 20 alkyl sulfates ("AS”), and polyhydroxy fatty acid amide surfactants.
  • liquid carriers such as, for example, water and C,-C 4 monohydric alcohols, thickening agents, viscosity control agents, di-(higher alkyl) cyclic amines, aqueous emulsions of predominantly linear polydialkyl or alkylaryl siloxanes absorbency enhancers, pH modifiers such as bases and acids, nonionic or other deflocculating agents, hydrotropes, colorants, perfumes, perfume carriers, preservatives, opacifiers, fluorescers, anti-shrinking agents, anti- wrinkle agents, anti-spotting agents, bactericides, germicides, fungicides, anti-corrosion agents, drape imparting agents, antistatic agents, ironing agents, wetting agents, strength additives such as carboxymethyl cellulose and water-soluble cationic polymers.
  • liquid carriers such as, for example, water and C,-C 4 monohydric alcohols, thickening agents, viscosity control agents, di-(higher alkyl) cyclic
  • PO propylene oxide
  • MEA is monoethanolamine
  • TEA is triethanolamine
  • MDEA is methyldiethanolamine
  • MAE is methyl amino ethanol (methyl monoethanolamine)
  • DMAE dimethyl amino ethanol
  • MDIPA is methyl diisopropanolamine
  • TIPA is triisopropanolamine
  • MeCI is methyl chloride Examples 1-2 Preparation of Polyalkanolamines with 2 Primary and 1 Secondary Hydroxyl Group
  • polyalkanolamines with 2 primary and 1 secondary hydroxyl group is by reaction in a 1 :1 mole ratio of DEA with propylene- or butylene oxide to form [bis(2-hydroxyethyl)]-[2-hydroxypropyl]amine (DEA-1 PO) or [bis(2- hydroxyethyl)]-[2-hydroxybutyl]amine (DEA-1 BO).
  • This reaction can be conveniently carried out by addition of the alkylene oxide to the DEA in a pressure vessel at temperatures from 50°C to 200°C, preferably from 80°C to 120°C and at a pressure of 1 to 80 bars.
  • alkylene oxide is added at 110°C to DEA (1 :1 mole ratio) in a 2 liter vessel, the temperature being controlled by cooling the vessel and controlling the feed rate of the alkylene oxide. This reaction takes usually 2 to 3 hours to a point where the pressure becomes constant.
  • the product thus obtained contains > 98 weight percent DEA-1 PO or DEA-1 BO and does not need further purification.
  • An example to prepare polyalkanolamines with 1 primary and 2 secondary hydroxyl groups is by reaction in a 1 :2 mole ratio of MEA with propylene- or butylene oxide to form [(2-hydroxyethyl)]-[bis(2-hydroxypropyl)]amine (MEA-2PO) or [(2- hydroxyethyl)]-[bis(2-hydroxybutyl)]amine (MEA-2BO).
  • This reaction can be conveniently carried out by addition of the alkylene oxide to the MEA in a pressure vessel at temperatures from 50°C to 200°C, preferably from 80°C to 120°C and at a pressure of 1 to 80 bars.
  • alkylene oxide is added at 110°C to MEA (2:1 mole ratio) in a 2 liter vessel, the temperature being controlled by cooling the vessel and controlling the feed rate of the alkylene oxide. This reaction takes usually 2 to 3 hours to a point where the pressure becomes constant.
  • the product obtained contains > 98 weight percent MEA-2PO or MEA-2BO and does not need further purification.
  • An example to prepare polyalkanolamines with 1 primary and 1 secondary hydroxyl group is by reaction in a 1 :1 mole ratio of MAE (N-methyl-2-aminoethanol) with propylene- or butylene oxide to form N-methyl-(2-hydroxyethyl)-(2-hydroxypropyl) amine (MAE-1 PO) or N-methyl-(2-hydroxyethyl)-(2-hydroxybutyl)amine (MAE-1 BO).
  • This reaction can be conveniently carried out by addition of the alkylene oxide to the MAE in a pressure vessel at temperatures from 50°C to 200°C, preferably from 80°C to 120°C and at a pressure of 1 to 80 bars.
  • alkylene oxide is added at 110°C to MEA (2:1 mole ratio) in a 2-liter vessel, the temperature being controlled by cooling the vessel and controlling the feed rate of the alkylene oxide. This reaction takes usually 2 to 3 hours to a point where the pressure becomes constant.
  • Polyalkanolamines having no primary hydroxyl groups can be prepared by standard methods known in the art. For example, these products can be made by reaction of ammonia or monoalkylamine with a C 3 or higher alkyleneoxide. In particular, ammonia can be reacted with propylene oxide to form TIPA and methylamine can be reacted with propyleneoxide to form MDIPA.
  • polyalkanolamines prepared in Examples 1 to 8 can be esterified with a carboxylic acid or a carboxylic acid mixture of choice under conventional conditions, known to those skilled in the art.
  • the polyalkanolamine is mixed with a carboxylic acid in the desired mole ratio in a vessel equipped with stirrer and a Dean-
  • esters obtained were analyzed by GC, GPC or NMR for unreacted alkanolamine, mono-, di- and triester.
  • the results, in percent by weight, are presented in Table I.
  • the results show the effect of using PO vs. BO, of changing the particular carboxylic acid, of changing the mole ratio of carboxylic acid reacted, and the effect of using different combinations of primary and secondary alcohols, and using di vs. trialkanolamines.
  • Examples 14, 15, 19 and 22 are comparative Examples which do not form a part of this invention but which were prepared according to the same procedure as the other Examples. These comparative examples demonstrate the manner in which the method of the present invention alters the resulting ester distribution.
  • reaction mixtures prepared in the earlier examples were quatemized with dimethylsulfate (DMS), or methyl chloride (MeCI).
  • DMS dimethylsulfate
  • MeCI methyl chloride
  • the percentage quatemized is reported in Table II.
  • the quatemization is carried out according to conditions known to those skilled in the art. In general, it consists of heating the polyalkanolamine diester with DMS or MeCI with or without additional additives to lower the melting point, at 30°C -150°C, preferably at 75°C -95°C for 1 to 5 hours.
  • compositions of the present invention tend to have lower melting points than the comparatives, which would aid in formulating the materials. Furthermore, the compositions of the present invention tend to be more hydrolytically stable, which is also advantageous, especially in liquid formulations.
  • Several of the mixtures (with a pH of about 8.5) were kept for 2 weeks at a temperature of about 35°C. The percentage of product which was found to have hydrolyzed is reported in Table III. This data shows the general trend that the compositions of the present invention show improved hydrolytic stability over the comparative examples.

Abstract

La présente invention concerne des manipulations de réactions d'estérification d'alkanolamines qui favorisent la formation de produits incomplètement estérifiés que l'on peut ensuite éventuellement neutraliser ou quaternariser. Les alkanolamines de départ sont synthétisées ou sélectionnées de sorte que leurs groupes alkanol ne sont pas tous primaires. Ces mélanges réactionnels présentent en composants soit di-estérifiés, soit mono-estérifiés, une concentration plus importante que les mélanges réactionnels connus jusqu'ici. Ces mélanges réactionnels peuvent être avantageusement utilisés comme agents adoucissants pour tissus ou papiers, comme détergents ainsi que comme produits de nettoyage et de soins personnels.
PCT/US1999/016981 1998-07-30 1999-07-28 Compositions utiles comme agents adoucissants ou nettoyants et pour les soins d'hygiene WO2000006678A1 (fr)

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EP99937527A EP1102833A1 (fr) 1998-07-30 1999-07-28 Compositions utiles comme agents adoucissants ou nettoyants et pour les soins d'hygiene
CA002338906A CA2338906A1 (fr) 1998-07-30 1999-07-28 Compositions utiles comme agents adoucissants ou nettoyants et pour les soins d'hygiene
AU52341/99A AU5234199A (en) 1998-07-30 1999-07-28 Composition useful for softening, cleaning, and personal care applications

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WO2001032813A1 (fr) * 1999-11-01 2001-05-10 Kao Corporation Composition de sels d'ammonium quaternaire
WO2007092020A1 (fr) * 2006-02-10 2007-08-16 Stepan Company Compositions actives pour le conditionnement de tissus
WO2007090567A1 (fr) * 2006-02-10 2007-08-16 Unilever Plc Compositions de conditionnement de tissus
WO2011123733A1 (fr) 2010-04-01 2011-10-06 The Procter & Gamble Company Produit assouplissant thermiquement stable
WO2011120822A1 (fr) 2010-04-01 2011-10-06 Evonik Degussa Gmbh Composition active d'adoucissant pour étoffe
WO2011123284A1 (fr) 2010-04-01 2011-10-06 The Procter & Gamble Company Produit assouplissant thermostable
EP2497844A1 (fr) * 2011-03-10 2012-09-12 Kao Corporation, S.A. Composition comprenant des esters quaternaire d'ammonium (esterquats) pour inhiber la corrosion des surfaces métalliques
US8361953B2 (en) 2008-02-08 2013-01-29 Evonik Goldschmidt Corporation Rinse aid compositions with improved characteristics
WO2013045565A1 (fr) 2011-09-28 2013-04-04 Taminco Liquides aqueux contenant un composé organique et une n-alkylamine substituée par du n-(2-hydroxyalkyle)
US8507425B2 (en) 2010-06-29 2013-08-13 Evonik Degussa Gmbh Particulate fabric softener comprising ethylenediamine fatty acid amides and method of making
US8563499B2 (en) 2010-04-01 2013-10-22 Evonik Degussa Gmbh Fabric softener active composition
WO2014092693A1 (fr) * 2012-12-11 2014-06-19 Colgate-Palmolive Company Composition d'esterquat présentant une teneur élevée en triesterquat
WO2014092692A1 (fr) * 2012-12-11 2014-06-19 Colgate-Palmolive Company Composition d'esterquat présentant une teneur élevée en triesterquat
JP2014523923A (ja) * 2011-07-28 2014-09-18 アンガス ケミカル カンパニー アミノアルコール化合物ならびに塗料およびコーティング用ゼロまたは低ｖｏｃ添加剤としてのそれらの使用
US8883712B2 (en) 2010-04-28 2014-11-11 Evonik Degussa Gmbh Fabric softening composition
US8883713B2 (en) 2012-01-30 2014-11-11 Evonik Industries Ag Fabric softener active composition
EP2899178A1 (fr) * 2014-01-23 2015-07-29 Kao Corporation, S.A. Compositions d'engrais solides antiagglomérant comprenant des composés d'ammonium ester quaternaire
US9441187B2 (en) 2012-05-07 2016-09-13 Evonik Degussa Gmbh Fabric softener active composition and method for making it
EP2970827A4 (fr) * 2013-03-15 2016-12-14 Stepan Co Compositions d'assouplissant pour textile
US10011806B2 (en) 2013-11-05 2018-07-03 Evonik Degussa Gmbh Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester
US10113137B2 (en) 2014-10-08 2018-10-30 Evonik Degussa Gmbh Fabric softener active composition
WO2021081969A1 (fr) * 2019-11-01 2021-05-06 Rhodia Operations Mélange de composés d'ammonium quaternaire et composition de conditionnement de tissus

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US7214718B1 (en) 1999-11-01 2007-05-08 Kao Corporation Quaternary ammonium salt composition
WO2001032813A1 (fr) * 1999-11-01 2001-05-10 Kao Corporation Composition de sels d'ammonium quaternaire
WO2007092020A1 (fr) * 2006-02-10 2007-08-16 Stepan Company Compositions actives pour le conditionnement de tissus
WO2007090567A1 (fr) * 2006-02-10 2007-08-16 Unilever Plc Compositions de conditionnement de tissus
US8361953B2 (en) 2008-02-08 2013-01-29 Evonik Goldschmidt Corporation Rinse aid compositions with improved characteristics
WO2011123284A1 (fr) 2010-04-01 2011-10-06 The Procter & Gamble Company Produit assouplissant thermostable
WO2011123733A1 (fr) 2010-04-01 2011-10-06 The Procter & Gamble Company Produit assouplissant thermiquement stable
US8183199B2 (en) 2010-04-01 2012-05-22 The Procter & Gamble Company Heat stable fabric softener
CN102834496B (zh) * 2010-04-01 2014-01-15 赢创德固赛有限公司 织物柔软剂活性组合物
US8569224B2 (en) 2010-04-01 2013-10-29 Evonik Degussa Gmbh Fabric softener active composition
CN102834496A (zh) * 2010-04-01 2012-12-19 赢创德固赛有限公司 织物柔软剂活性组合物
WO2011120822A1 (fr) 2010-04-01 2011-10-06 Evonik Degussa Gmbh Composition active d'adoucissant pour étoffe
US8563499B2 (en) 2010-04-01 2013-10-22 Evonik Degussa Gmbh Fabric softener active composition
JP2013525617A (ja) * 2010-04-01 2013-06-20 ザ プロクター アンド ギャンブル カンパニー 熱安定性柔軟仕上げ剤
US8883712B2 (en) 2010-04-28 2014-11-11 Evonik Degussa Gmbh Fabric softening composition
US8507425B2 (en) 2010-06-29 2013-08-13 Evonik Degussa Gmbh Particulate fabric softener comprising ethylenediamine fatty acid amides and method of making
WO2012120143A1 (fr) * 2011-03-10 2012-09-13 Kao Corporation, S.A. Composition d'ammonium quaternaire destinée à inhiber la corrosion
EP2497844A1 (fr) * 2011-03-10 2012-09-12 Kao Corporation, S.A. Composition comprenant des esters quaternaire d'ammonium (esterquats) pour inhiber la corrosion des surfaces métalliques
JP7057769B2 (ja) 2011-07-28 2022-04-20 アンガス ケミカル カンパニー アミノアルコール化合物ならびに塗料およびコーティング用ゼロまたは低ｖｏｃ添加剤としてのそれらの使用
JP2014523923A (ja) * 2011-07-28 2014-09-18 アンガス ケミカル カンパニー アミノアルコール化合物ならびに塗料およびコーティング用ゼロまたは低ｖｏｃ添加剤としてのそれらの使用
JP2020002360A (ja) * 2011-07-28 2020-01-09 アンガス ケミカル カンパニー アミノアルコール化合物ならびに塗料およびコーティング用ゼロまたは低ｖｏｃ添加剤としてのそれらの使用
US9605163B2 (en) 2011-07-28 2017-03-28 Angus Chemical Company Aminoalcohol compounds and their use as zero or low VOC additives for paints and coatings
WO2013045565A1 (fr) 2011-09-28 2013-04-04 Taminco Liquides aqueux contenant un composé organique et une n-alkylamine substituée par du n-(2-hydroxyalkyle)
US8883713B2 (en) 2012-01-30 2014-11-11 Evonik Industries Ag Fabric softener active composition
US9441187B2 (en) 2012-05-07 2016-09-13 Evonik Degussa Gmbh Fabric softener active composition and method for making it
WO2014092693A1 (fr) * 2012-12-11 2014-06-19 Colgate-Palmolive Company Composition d'esterquat présentant une teneur élevée en triesterquat
US9388367B2 (en) 2012-12-11 2016-07-12 Colgate-Palmolive Company Esterquat composition having high triesterquat content
US9476012B2 (en) 2012-12-11 2016-10-25 Colgate-Palmolive Company Esterquat composition having high triesterquat content
CN104837976A (zh) * 2012-12-11 2015-08-12 高露洁-棕榄公司 具有高三酯季铵盐含量的酯季铵盐组合物
US9732307B2 (en) 2012-12-11 2017-08-15 Colgate-Palmolive Company Esterquat composition having high triesterquat content
WO2014092692A1 (fr) * 2012-12-11 2014-06-19 Colgate-Palmolive Company Composition d'esterquat présentant une teneur élevée en triesterquat
EP2970827A4 (fr) * 2013-03-15 2016-12-14 Stepan Co Compositions d'assouplissant pour textile
AU2013381757B2 (en) * 2013-03-15 2017-07-13 Stepan Company Fabric softener compositions
US10011807B2 (en) 2013-03-15 2018-07-03 Stepan Company Fabric softener compositions
US10011806B2 (en) 2013-11-05 2018-07-03 Evonik Degussa Gmbh Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester
EP2899178A1 (fr) * 2014-01-23 2015-07-29 Kao Corporation, S.A. Compositions d'engrais solides antiagglomérant comprenant des composés d'ammonium ester quaternaire
US10113137B2 (en) 2014-10-08 2018-10-30 Evonik Degussa Gmbh Fabric softener active composition
WO2021081969A1 (fr) * 2019-11-01 2021-05-06 Rhodia Operations Mélange de composés d'ammonium quaternaire et composition de conditionnement de tissus

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