Concentrated liquid esterquat composition

Abstract

A clear, stable liquid concentrate composition is disclosed, comprising 30% to 90% by weight of esterquat actives and 10% to 50% by weight of a specific solvent system. The esterquat actives are the quaternized reaction product of a fatty acyl source having an iodine value of 40 to 130, reacted with an alkanolamine in a molar ratio of fatty acyl to alkanolamine of 1.0:1 to 2.2:1. The liquid concentrate composition has a VOC content of less than 5%, a biorenewable carbon index (BCI) of at least 20, and a viscosity of less than 5000 cP at 25°C. The liquid concentrate composition can be easily diluted with water to form a stable aqueous dispersion.

Description

[Technical Field]

[0001] The present technology relates to clear, concentrated esterquat compositions that utilize esterquat actives that are chemically stable, stable on storage, biodegradable, and water-dispersible in the composition. The concentrated liquid compositions can be used without dilution or can be easily dispersed in water to form a stable liquid dispersion. The concentrated liquid esterquat compositions are particularly useful in fabric softening applications. [Background technology]

[0002] Liquid fabric softening compositions that soften fabrics during the rinse cycle are known. Such compositions typically contain softening actives in amounts ranging from about 5% to about 15% by weight, with the remainder being primarily water. More concentrated compositions, i.e., compositions having actives greater than 15%, are desirable because they require less packaging and therefore have a lower environmental impact, for example, by reducing shipping costs and generating less waste.

[0003] One of the problems associated with concentrated fabric softening compositions is that they are not stable during storage, especially when stored at elevated temperatures or at freezing temperatures. This instability can manifest as an increase in the viscosity of the product upon storage, to the point where the product is no longer pourable. As a result, typical commercial liquid fabric softener compositions today have a softening active concentration of about 15% by weight or less.

[0004] Another challenge with concentrated fabric softening compositions is that they often require a solvent to achieve an acceptable concentrated aqueous dispersion. The addition of a solvent is typically required to achieve a product with a sufficiently low viscosity in the molten state that it can be pumped using conventional equipment. The added solvent is typically a volatile organic compound (VOC), such as isopropanol or ethanol, which is undesirable from an environmental standpoint. Additionally, strict regulations limiting VOCs have been proposed, making it important to limit or eliminate VOC-causing solvents.

[0005] There is also a trend in the consumer goods market to create products with ingredients based on renewable plant- and animal-based resources rather than fossil fuels. Such ingredients are considered "green" or "natural" because they are derived from renewable and / or sustainable resources. As a result, they are more environmentally friendly than fossil-fuel-derived materials. Ingredients with a high Biorenewable Carbon Index (BCI), for example, a BCI above 80, indicate that the ingredient contains carbon derived primarily from plant, animal, or marine-based sources.

[0006] A need exists for highly concentrated fabric softener active systems that can remain stable in concentrated form during storage and yet can be readily diluted with water at room temperature to form stable fabric softening dispersions without gelling. There is also a need for stable concentrated liquid fabric softener compositions that can be made from renewable resources and have ingredients that do not require VOC solvents. Summary of the Invention

[0007] In a first aspect, the present technology provides a clear and stable liquid composition, the composition comprising: (A) about 30% to about 80% by weight, based on the weight of the composition, of one or more esterquats, the one or more esterquats being quaternized reaction products of a fatty acyl source having an iodine value of 40 to 130, reacted with an alkanolamine in a molar ratio of fatty acyl to alkanolamine of about 1.0:1 to about 2.2:1; and (B) about 20% to about 50% by weight, based on the weight of the composition, of a solvent system, the solvent system comprising: (i) a mixture of one or more polyethylene glycols having a number average molecular weight of 130 to 700 and one or more fatty acid amides having the following general structure:

[0008] [ka] wherein R has 6 to 20 carbon atoms, is branched or linear, is saturated or has an unsaturated double bond, and optionally contains one or more hydroxyl groups (a hydroxyl group is an -OH group); and R 1 and R 2 are independently hydrogen, a C1-C6 alkyl group, or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; and (C) optionally, from 0 wt. % up to 30 wt. % water, wherein the composition has a measured viscosity at 25°C of less than 5000 cP.

[0009] In another aspect, the present technology provides a clear, stable liquid composition, the composition comprising: (A) about 30% to about 90% by weight, based on the weight of the composition, of one or more esterquats, the one or more esterquats being quaternized reaction products of a fatty acyl source having an iodine value of 40 to 130, reacted with an alkanolamine in a molar ratio of fatty acyl to alkanolamine of about 1.0:1 to about 2.2:1; and (B) about 10% to about 50% by weight, based on the weight of the composition, of a solvent system comprising a mixture of one or more glycol ethers selected from the group consisting of 2-butoxyethanol, 2-phenoxyethanol, 2-benzyloxyethanol, 2(2-methoxyethoxy)ethanol, 2(2-ethoxyethoxy)ethanol, dipropylene glycol monomethyl ether, dibutoxyethane, and combinations thereof, and one or more fatty acid amides having the following general structure: [ka] wherein R has 6 to 20 carbon atoms, is branched or linear, is saturated or has an unsaturated double bond, and optionally contains one or more hydroxyl groups; and R 1 and R 2 are independently hydrogen, a C1-C6 alkyl group, or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; and (C) optionally, from 0 wt. % up to 30 wt. % water, wherein the composition has a measured viscosity at 25°C of less than 5000 cP.

[0010] In another aspect, the present technology provides a clear and stable composition, the composition comprising: (A) about 30% to about 90% by weight, based on the weight of the composition, of one or more esterquats, the one or more esterquats being quaternized reaction products of a fatty acyl group having an iodine value of 40 to 130 and an alkanolamine, in a molar ratio of fatty acyl to alkanolamine of about 1.0:1 to about 2.2:1; and (B) about 10% to about 50% by weight, based on the weight of the composition, of a solvent system, the solvent system comprising one or more 1,3-dialkoxy-2-propanol having the general formula: [ka] In the formula, R a and R b are independently a C1-C6 alkyl group or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; and (C) optionally, from 0% to a maximum of 30% by weight of water; The composition has a measured viscosity at 25°C of less than 5000 cP.

[0011] In another aspect, the present technology provides a clear and stable composition, the composition comprising: (A) about 55% to about 85% by weight, based on the weight of the composition, of one or more esterquats, the one or more esterquats being quaternized reaction products of a fatty acyl group having an iodine value of 40 to 130 with an alkanolamine in a molar ratio of fatty acyl to alkanolamine of about 1.0:1 to about 2.2:1; and (B) about 15% to about 45% by weight, based on the weight of the composition, of a solvent system, the solvent system comprising one or more fatty amides having the general structure: [ka] wherein R has 6 to 20 carbon atoms, is branched or linear, is saturated or has an unsaturated double bond, and optionally contains one or more hydroxyl groups; and R 1 and R 2 are independently hydrogen, a C1-C6 alkyl group, or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; and (C) optionally, 0% to a maximum of 10% by weight of water, wherein the composition has a measured viscosity at 25°C of less than 5000 cP.

[0012] In a further aspect, the present technology relates to a method of making a fabric softener composition, the method comprising the steps of: (A) providing a concentrated fabric softening composition, the concentrated fabric softening composition comprising: (i) about 30% to about 80% by weight, based on the weight of the concentrated fabric softening composition, of one or more esterquat actives, the one or more esterquat actives being a quaternized reaction product of a fatty acyl source having an iodine value of 40 to 130, reacted with an alkanolamine in a fatty acyl to alkanolamine molar ratio of about 1.0:1 to about 2.2:1; and (ii) about 20% to about 50% by weight, based on the weight of the concentrated fabric softening composition, of a solvent system comprising a mixture of one or more polyethylene glycols having a number average molecular weight of 130 to 700 and one or more fatty acid amides having the general structure: [ka] wherein R has 6 to 20 carbon atoms, is branched or linear, is saturated or has an unsaturated double bond, and optionally contains one or more hydroxyl groups; and R 1 and R 2are independently hydrogen, a C1-C6 alkyl group, or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; and (iii) optionally, from 0 wt. % to up to 30 wt. % water, wherein the concentrated fabric softening composition has a measured viscosity of less than 5000 cP at 25° C.; and (B) mixing the concentrated fabric softening composition in water to form a stable aqueous dispersion comprising 2 wt. % to 22 wt. % esterquat actives, based on the total weight of the dispersion, thereby making the softener composition.

[0013] In a further aspect, the present technology provides a method of making a fabric softener composition, the method comprising the steps of: (A) providing a concentrated fabric softening composition, the concentrated fabric softening composition comprising: (i) about 30% to about 90% by weight, based on the weight of the concentrated fabric softening composition, of one or more esterquat actives, the one or more esterquat actives being a quaternized reaction product of a fatty acyl source having an iodine value of 40 to 130, reacted with an alkanolamine in a fatty acyl to alkanolamine molar ratio of about 1.0:1 to about 2.2:1; and (ii) about 10% to about 50% by weight, based on the weight of the concentrated fabric softening composition, of a solvent system comprising one or more 1,3-dialkoxy-2-propanol having the general formula: [ka] In the formula, R a and R bare independently a C1-C6 alkyl group or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched, and (C) optionally from 0% to a maximum of 30% by weight of water, wherein the concentrated fabric softening composition has a measured viscosity of less than 5000 cP at 25°C; and (B) mixing the concentrated fabric softening composition in water to form a stable aqueous dispersion comprising 2% to 22% by weight of esterquat actives, based on the total weight of the dispersion, thereby making the softener composition.

[0014] In a further aspect, the present technology provides a method of making a fabric softener composition, the method comprising the steps of: (A) providing a concentrated fabric softening composition, the concentrated fabric softening composition comprising: (i) about 30% to about 90% by weight, based on the weight of the concentrated fabric softening composition, of one or more esterquat actives, the one or more esterquat actives being a quaternized reaction product of a fatty acyl source having an iodine value of 40 to 130, reacted with an alkanolamine in a fatty acyl to alkanolamine molar ratio of about 1.0:1 to about 2.2:1; one or more esterquat actives; and (ii) about 10% to about 50% by weight of a solvent system, based on the weight of the concentrated fabric softening composition, the solvent system comprising a mixture of one or more glycol ethers selected from the group consisting of 2-butoxyethanol, 2-phenoxyethanol, 2-benzyloxyethanol, 2(2-methoxyethoxy)ethanol, 2(2-ethoxyethoxy)ethanol, dipropylene glycol monomethyl ether, dibutoxyethane, and combinations thereof, and one or more fatty acid amides having the general structure: [ka] wherein R has 6 to 20 carbon atoms, is branched or linear, is saturated or has an unsaturated double bond, and optionally contains one or more hydroxyl groups; and R 1 and R2 are independently hydrogen, a C1-C6 alkyl group, or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; and (C) optionally from 0% to a maximum of 30% by weight of water, wherein the composition has a measured viscosity of less than 5000 cp at 25°C; and (B) mixing the concentrated fabric softening composition in water to form a stable aqueous dispersion comprising 2% to 22% by weight of esterquat actives, based on the total weight of the dispersion, thereby making a softener composition.

[0015] In an additional aspect, the present technology relates to a method of making a fabric softener composition, the method comprising the steps of: (A) providing a concentrated fabric softening composition, the concentrated fabric softening composition comprising: (i) about 55% to about 85% by weight, based on the weight of the concentrated fabric softening composition, of one or more esterquat actives, the one or more esterquat actives being a quaternized reaction product of a fatty acyl source having an iodine value of 40 to 130, reacted with an alkanolamine in a fatty acyl to alkanolamine molar ratio of about 1.0:1 to about 2.2:1; and (ii) about 15% to about 45% by weight, based on the weight of the concentrated fabric softening composition, of a solvent system comprising one or more fatty acid amides having the general structure: [ka] wherein R has 6 to 20 carbon atoms, is branched or linear, is saturated or has an unsaturated double bond, and optionally contains one or more hydroxyl groups; and R 1 and R 2are independently hydrogen, a C1-C6 alkyl group, or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; and (iii) optionally, from 0 wt. % to a maximum of 10 wt. % water, wherein the concentrated fabric softening composition has a measured viscosity of less than 5000 cP at 25° C.; and (B) mixing the concentrated fabric softening composition in water to form a stable aqueous dispersion comprising 2 wt. % to 22 wt. % esterquat actives, based on the total weight of the dispersion, thereby making the softener composition. DETAILED DESCRIPTION OF THE INVENTION

[0016] While the technology described herein has been described in connection with one or more preferred embodiments, those skilled in the art will recognize that the technology is not limited to only those particular embodiments. On the contrary, the technology described herein includes all alternatives, modifications, and equivalents that may be included within the spirit and scope of the appended claims.

[0017] definition "Biorenewable Carbon Index (BCI)" refers to an estimate of the proportion of carbon that comes from biorenewable sources, calculated based on the number of biorenewable carbons divided by the total number of carbons in the molecule.

[0018] As used herein, "bio-renewable" is defined as derived from animal, plant, or marine materials.

[0019] A "transparent" or "clear" composition is defined as a composition having a light transmittance of greater than about 50 at a wavelength of 420 nanometers using a 1-centimeter cuvette, where the composition is measured at 25° C. in the absence of dyes and opacifiers. Alternatively, the transparency of a composition may be measured as having an absorbance (A) of less than about 0.3 at 420 nanometers, which is equivalent to a transmittance of greater than about 50 using the same cuvette. The relationship between absorbance and transmittance is as follows: Transmittance = 100 (1 / inverse logarithm A)

[0020] "VOC" refers to volatile organic compounds. Such compounds have a vapor pressure greater than 2 mmHg at 25°C, fewer than 7 carbon atoms, and a boiling point less than 120°C at atmospheric pressure.

[0021] Esterquat fabric softener compound The concentrated liquid compositions of the present invention contain, as the primary actives, an esterquat cationic material, which is the quaternization reaction product of a fatty acyl source reacted with an alkanolamine. Generally, the esterquat actives of the present invention are prepared by mixing a natural oil or other fatty acid feedstock with an alkanolamine, typically at an initial temperature at which the natural oil or fatty acid feedstock is liquid or molten, optionally adding a catalyst, and then heating the reaction mixture until the desired esteramine reaction product is obtained, as evidenced by its acid and base values. The fatty acid feedstock is reacted with an alkanolamine in a molar ratio of fatty acyl groups to alkanolamine of about 1.0:1 to about 2.2:1 to form an esteramine intermediate. The esteramine intermediate is then quaternized using an alkylating agent to obtain the esterquat product. Alkylating agents for preparing esterquats are known in the art and include, for example, dimethyl sulfate, methyl chloride, diethyl sulfate, benzyl chloride, ethylbenzyl chloride, methyl bromide, and epichlorohydrin. The resulting esterquat product is a mixture of quaternized monoester, diester, and, depending on the starting alkanolamine, triester components, and, optionally, amounts of one or more reactants, intermediates, and by-products, including, but not limited to, free amines and free fatty acids or parent fatty acyl compounds, or derivatives thereof.

[0022] The fatty acyl source for preparing the esterquats can be a variety of starting materials, such as free fatty acids, fatty acid esters, or acid chlorides corresponding to fatty acids. The free fatty acids can be isolated, such as a single purified fatty acid, or can be a combination, such as a mixture of fatty acids characteristic of the fatty acid component of the glyceride esters in natural oils. The fatty acid esters can be glycerides, such as mono-, di-, and / or triglycerides, or alkyl esters of fatty acids, such as methyl or ethyl esters of fatty acids. The fatty acid esters can be derived from a single fatty acid or a mixture of fatty acids, such as from a natural fatty acid source or natural oil. In some embodiments, fatty acids or alkyl ester derivatives thereof are preferred over natural oils as the fatty acyl source.

[0023] Esterquats may be prepared from C8-32 fatty acids or their alkyl ester derivatives, which may be saturated, unsaturated, or a mixture of saturated and unsaturated fatty acids. Preferred fatty acids are those having a carbon chain length of 16 to 20 carbon atoms. The fatty acids may be derived from a variety of sources, such as sunflower, canola, corn, cottonseed, flaxseed, peanut, meadowfoam, soybean, walnut, jojoba, palm, borage, safflower, or rapeseed, or mixtures thereof. In some embodiments, the fatty acids are derived from canola oil or low erucic acid rapeseed oil (LEAR). Preferred fatty acids contain at least 50% by weight, or at least 60% by weight, unsaturated fatty acid groups with at least one carbon-carbon double bond, and have an iodine value in the range of 40 to 130, preferably 50 to 130, and more preferably 60 to 130.

[0024] The iodine value represents the average iodine value of the parent fatty acid acyl compound or all the fatty acids present in the esterquat. In the present invention, the iodine value is defined as the number of grams of iodine that will react with 100 grams of the parent compound. The method for calculating the iodine value of a parent fatty acid acyl compound / acid is known in the art and involves dissolving a predetermined amount (0.1-3 g) in approximately 15 ml of chloroform. The dissolved parent fatty acid acyl compound / acid is then reacted with 25 ml of iodine monochloride in 0.1 M acetic acid solution. To this end, 20 ml of 10% potassium iodide solution and approximately 150 ml of deionized water are added. After the halogen addition, the excess iodine monochloride is determined by titration with 0.1 M sodium thiosulfate solution in the presence of blue starch indicator powder. A blank is simultaneously determined using the same amount of reagent and under the same conditions. The iodine value can be calculated by the difference between the volume of sodium thiosulfate used in the blank and the volume of sodium thiosulfate used in the reaction with the parent fatty acyl compound or fatty acid.

[0025] The amount of unsaturated fatty acid groups in the esterquat can affect the ability to obtain a concentrated liquid composition that maintains stability. Esterquats made from fatty acid sources having an average iodine value less than about 40 can result in unstable concentrated liquid compositions.

[0026] Alkanolamines useful in preparing esterquat actives generally correspond to the following general formula: [ka] wherein R1, R2, and R3 are independently selected from C1-C6 alkyl groups or hydroxyalkyl groups. Suitable alkanolamines include triethanolamine (TEA), methyldiethanolamine (MDEA), ethyldiethanolamine, dimethylamino-N-(2,3-propanediol), diethylamino-N-(2,3-propanediol), methylamino-N-2-ethanol-N-2,3-propanediol, and ethylamino-N-2-ethanol-N-2,3-propanediol, and mixtures thereof. The molar ratio of fatty acid to alkanolamine is about 1.0:1 to about 2.2:1. In some embodiments, the alkanolamine is triethanolamine (TEA) and the molar ratio of fatty acid group to TEA is about 1.3:1 to about 2.2:1, or about 1.3:1 to 1.8:1. In another embodiment, the alkanolamine is MDEA and the molar ratio of fatty acid group to MDEA is from about 1.0:1 to about 2.0:1.

[0027] A preferred esterquat is a TEA-based esterquat having the following chemical structure: [ka] Each R is independently selected from a C5-31 alkyl or alkenyl group, or a C7-21 alkyl or alkenyl group, or a C11-21 alkyl or alkenyl group, or at least predominantly a C13-17 alkyl or alkenyl group, and may be linear or branched. Preferably, the compound of Formula I contains different R groups derived from a fatty acid source having an average iodine value of 60 to 130. R1 represents a C1-4 alkyl or hydroxyalkyl group, or a C2-4 alkenyl group; [ka] (i.e., a front or back ester bond); n is an integer selected from 0 to 4, or an integer selected from 2 to 4; m is 1 for monoesterquats, 2 for diesterquats, or 3 for triesterquats, m indicates the number of moieties directly pendant from the N atom; and X is an ionic group such as, for example, a halide or an alkyl sulfate, such as a C alkyl sulfate or hydroxyalkyl sulfate, or a C alkenyl sulfate. Specific contemplated anionic groups include chloride, methyl sulfate, or ethyl sulfate.

[0028] Concentrated liquid compositions contain from about 30% to about 90% by weight, alternatively from about 35% to about 85% by weight, alternatively from about 40% to about 80% by weight, alternatively from about 45% to about 75% by weight, alternatively from about 45% to about 70% by weight, alternatively from about 50% to about 60% by weight, alternatively from about 55% to about 85% by weight of the esterquat actives, based on the total weight of the composition.

[0029] solvent The concentrated liquid composition also includes about 10% to about 50% by weight, alternatively about 15% to about 45%, alternatively about 20% to about 40%, alternatively about 25% to about 35% by weight of a solvent system, the solvent system comprising one or more solvents. An important aspect of the present technology is that the solvent system used in the concentrated fabric softening composition has low or no VOC content and primarily comprises solvents derived from biorenewable resources. For example, traditional solvents used in fabric softening compositions, such as ethanol, propanol, and butanol, are VOC solvents, derived from petroleum sources, or both, and are undesirable for use in the concentrated fabric softening compositions of the present technology. However, in some embodiments, the solvent system may include a VOC solvent, provided that the VOC solvent contributes no more than 5% by weight, preferably no more than 2% by weight, of VOC to the concentrated fabric softening composition, based on the total weight of the composition. Preferably, only non-VOC solvents are used in the composition.

[0030] It is also desirable that the solvent selected have a BCI greater than 50, alternatively greater than 60, alternatively greater than 70, alternatively greater than 80, or alternatively greater than 90. In some embodiments, solvents having a BCI less than 50, including solvents having a BCI of 0 (i.e., 100% petroleum-based), can be used in combination with solvents having a high BCI (greater than 50) to achieve an overall solvent system having a BCI of at least 20, alternatively 20-60, alternatively 40-60, alternatively at least 50, or alternatively at least 60.

[0031] Solvents that can be used in the solvent system include polyethylene glycol, fatty acid amides, 1,3-dialkoxy-2-propanol, glycol ethers, or combinations thereof. Polyethylene glycols that can be used are those having a number average molecular weight ranging from 130 to 700, alternatively 170 to 400, alternatively 190 to 300, or alternatively 195 to 210. The number average molecular weight can be determined by methods known in the art, such as size exclusion chromatography. One example of a suitable polyethylene glycol (PEG) solvent is PEG 200 (also known as PEG-4), which has a number average molecular weight of approximately 200. PEG 200 is a non-VOC solvent and is available in 100% plant-based form from Acme-Hardesty. When derived from 100% plant-based sources, PEG 200 has a BCI of 100.

[0032] Fatty acid amides that can be used in the solvent system have the following general structure: [ka] wherein R is a branched or linear, saturated or unsaturated alkyl or alkenyl, or a combination thereof, having 6 to 20, preferably 8 to 14, carbon atoms. In some embodiments, R may contain one or more hydroxyl groups. 1 and R 2are independently hydrogen, a C1-C6 alkyl group, or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched, or a mixture thereof. Examples of raw materials that can be used to make alkylamides include lauric fatty acids, myristyl fatty acids, coconut fatty acids, soybean fatty acids, and ricinoleic fatty acids, or the corresponding methyl esters of these raw materials. 1 Groups and R 2 Specific examples of groups include methyl, ethyl, and 2-propanol. Commercial examples of dialkylamides include, but are not limited to, di-isopropylamide, available under the trade name COLA® Liquid from Colonial Chemical, Inc., and dimethylamides available commercially from Stepan Company under the trademarks NINOL® and Hallcomid®. One example of a suitable alkylamide is NINOL® CAA, a mixture of dimethyl lauramide and dimethyl myristamide (CAA), available from Stepan Company. CAA is derived primarily from renewable resources, has a BCI of 86, and is a non-VOC solvent. Other examples of suitable alkylamides available from Stepan Company are HALLCOMID® M-10 (N,N-dimethylcapramide; M-10) and HALLCOMID® M-8-10 (a mixture of N,N-dimethylcaprylamide and N,N-dimethylcapramide; M-8-10). All carbon in these molecules, except for the methyl group on the nitrogen, is derived from plant sources. Another example is STEPOSOL® MET-10U (N,N-dimethyl 9-decenamide; MET-10U), also available from Stepan Company.

[0033] The 1,3-dialkoxy-2-propanols that may be used in the solvent system have the following general structure: [ka] In the formula, Ra and R b are independently a C1-C6 alkyl group or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, when three or more carbon atoms are present, optionally branched or a mixture thereof. An example of a suitable 1,3-dialkoxy-2-propanol solvent is 1,3-diethoxy-2-propanol (DEP). DEP is not a VOC solvent. DEP can be prepared by a synthetic route that utilizes biorenewable feedstocks rather than petroleum-based feedstocks. When derived from biorenewable feedstocks, DEP has a BCI of 100.

[0034] Glycol ethers that can be used in the solvent system are preferably non-VOC and are selected from the group consisting of 2-butoxyethanol, 2-phenoxyethanol, 2-benzyloxyethanol, 2(2-methoxyethoxy)ethanol, 2(2-ethoxyethoxy)ethanol, dipropylene glycol monomethyl ether, dibutoxyethane, and combinations thereof. One example of a suitable glycol ether is dipropylene glycol monomethyl ether (DPM). DPM has a BCI of 0, but can be combined with solvents that have a higher BCI, such as CAA, resulting in an overall solvent system BCI of at least 20.

[0035] The solvent in the solvent system is selected so that the concentrated esterquat composition is clear, chemically stable, storage stable, and water-dispersible. In some embodiments, a clear, stable, water-dispersible concentrated composition can be obtained using a solvent system comprising a single solvent. In other embodiments, it may be necessary to use a mixture of certain solvents to achieve the desired stability and water-dispersibility. A concentrated composition comprising 1,3-dialkyl-2-propanol as the sole solvent has been found to be stable and water-dispersible. A 1,3-dialkyl-2-propanol solvent can also be combined with one or more of the other solvents listed above to form a solvent system. In some embodiments, a stable, water-dispersible concentrated composition can be obtained using a fatty acid amide (as defined above) as the sole solvent in an amount of about 15% to about 45% by weight of the composition. It has also been found that a solvent system comprising a mixture of at least one polyethylene glycol and at least one fatty acid amide, as defined above, can provide a clear, stable, water-dispersible concentrated composition. The weight ratio of polyethylene glycol to fatty acid amide in the solvent system may range from 1:3 to 3:1, or from 1:2 to 2:1. In one embodiment, the solvent system comprises a mixture of PEG200 and CAA. Solvent systems comprising a mixture of at least one glycol ether and at least one fatty acid amide, as defined above, can also provide clear, stable, water-dispersible concentrate compositions. In some embodiments, the weight ratio of glycol ether to fatty acid amide in the solvent system is about 2:1. In one embodiment, the solvent system comprises a mixture of DPM and CAA.

[0036] The viscosity of the concentrated liquid composition is less than 5000 cP at 25°C, preferably less than 3000 cP at 25°C, and most preferably less than 1000 cP at 25°C.

[0037] Liquid Carrier Concentrated liquid esterquat compositions can contain from 0% to up to 30% by weight of a liquid carrier, as needed, to achieve a composition viscosity of less than 5,000 cP at 25°C. Water is a preferred liquid carrier due to its low cost, relative availability, safety, and environmental friendliness. It should be understood that water should not be considered part of the solvent system in any of the compositions of the present invention. In some embodiments, concentrated compositions have a viscosity of less than 5,000 cP without the addition of water or other liquid carrier. In such embodiments, the composition may comprise from about 50% to about 90% by weight of esterquat and from about 10% to about 50% by weight of solvent. Water-free concentrated liquid compositions have good stability during long-term storage due to the absence of water, which can cause hydrolysis of the esterquat.

[0038] Optional Ingredients It is anticipated that the concentrated liquid composition may optionally contain additional ingredients, if desired or necessary. Additional ingredients include, but are not limited to, nonionic surfactants, cationic surfactants, amphoteric surfactants, silicones such as polydimethylsiloxane, aminosilicone, or ethoxylated silicone, cationic polymers, or any combination thereof. The optional ingredients may be added to the concentrated liquid composition in an amount of 0 to about 3% by weight of the composition.

[0039] Supplementary ingredients Adjunct ingredients may be added to the compositions of the present technology. The term "adjunct ingredients" includes the following: dispersants, stabilizers, pH control agents, metal ion control agents, colorants, bleaching agents, dyes, odor control agents, pro-perfumes, cyclodextrins, perfumes, solvents, stain repellents, preservatives, antimicrobial agents, chlorine scavengers, anti-shrinkage agents, fabric crisping agents, spotting agents, antioxidants, rust inhibitors, thickeners, drape and form control agents. agents), leveling agents, antistatic agents, drapery control agents, sanitizing agents, disinfectants, bacterial control agents, mold control agents, mildew control agents, antiviral agents, drying agents, stain resistance agents, malodor control agents, fabric deodorizers, chlorine bleach malodor control agents, dye fixatives, dye transfer inhibitors, color retention agents, color restoration agents, regenerators, fade resistance agents, whiteness enhancers, anti-abrasion agents, abrasion resistance agents, fabric quality agents, anti-wear agents, rinse aids, UV protection agents, sun fade resistance agents, insect repellents, anti-allergy agents, enzymes, flame retardants, waterproofing agents, fabric comfort agents, water conditioning agents, shrinkage resistance agents, stretch resistance agents, and combinations thereof. Adjunct ingredients may be added to the concentrate compositions in amounts of 0 to about 3% by weight of the composition.

[0040] Composition characteristics The concentrated liquid esterquat compositions of the present technology are clear, transparent, and desirably have a transmittance greater than about 50 at a wavelength of 420 nanometers when measured at 25°C in the absence of dyes and opacifiers. The compositions have a measured viscosity of less than 5,000 cP at 25°C, alternatively less than 3,000 cP at 25°C, alternatively less than 1,000 cP at 25°C, and a VOC content of less than 2 wt. % based on the total weight of the composition. In some embodiments, the solvent system has a BCI of at least 50. The solvent system can incorporate hydrophobic components into the composition. Therefore, the solvent system may allow the concentrated liquid composition to contain a high amount of perfume or fragrance ingredients. A high amount of perfume or fragrance ingredients is about 1% to 12% by weight, alternatively about 2% to 8% by weight, alternatively about 2% to 5% by weight.

[0041] Method for Making Concentrated Softening Composition The concentrated liquid compositions of the present technology may be made by simply mixing the esterquat with the solvent system. When water is also included in the composition, it is preferred to mix the solvent system and water together and then add the esterquat. Mixing can be done at ambient temperature; it is not necessary to heat the ingredients before mixing. However, it may be desirable to heat the ingredients to facilitate mixing or to reduce the viscosity of the esterquat to make it easier to handle. Optional and auxiliary ingredients can be added at any time.

[0042] Method for making diluted compositions from concentrates It is contemplated that the concentrated liquid composition can be used directly without dilution. It is also contemplated that the concentrated liquid composition can be diluted, preferably with water, prior to use to a concentration of about 2% to about 22% by weight, preferably about 3% to about 8% by weight, of the esterquat actives, based on the total weight of the diluted composition. It is contemplated that some embodiments of the concentrated liquid composition can be easily dispersed in water, so that dilution can be performed by the consumer. Such use offers several advantages, such as reduced packaging requirements (due to the concentrated product), reduced transportation energy requirements, and reduced transportation costs, due to the need to transport less water.

[0043] It is also contemplated that a minimal amount of solvent system may be used to make the esterquats flowable for shipping, e.g., an amount that provides a viscosity of about 5,000 cP or less at 25° C. The remaining amount of solvent may then be added at that point to make the complete liquid concentrate composition.

[0044] The concentrated liquid compositions of the present technology may be shipped in concentrated form to consumer product manufacturers who do not have access to equipment for making conventional liposomal esterquat dispersions. Some embodiments of the concentrated liquid compositions can be easily dispersed in water without the use of high-shear mixing or other specialized equipment, allowing consumer product manufacturers without such equipment to easily produce diluted products with 2-22% actives by weight. In some embodiments, when diluting concentrated liquid compositions to concentrations of esterquat actives greater than about 8% by weight of the diluted composition, it may be useful to include an ionizing salt. Ionizing salts are typically used in high-concentration dispersions to reduce or control viscosity and / or stabilize diluted formulations.

[0045] A wide variety of ionizable salts can be used in the diluted dispersion. Examples of suitable salts include halides of metals from Groups IA and IIA of the Periodic Table, such as calcium chloride, magnesium chloride, sodium chloride, potassium bromide, and lithium chloride. The amount of ionizable salt used depends on the amount of active ingredient used in the composition and can be adjusted according to the manufacturer's needs. Typical amounts of salt used to control the viscosity of the composition are about 20 to about 20,000 ppm, preferably about 20 to about 11,000 ppm, by weight of the diluted composition. Optional or supplemental ingredients may be added by the product manufacturer to produce the final diluted product. Desirably, the concentrated liquid compositions of the present technology are stable concentrates that, when diluted prior to use, form stable liquid dispersions. A stable liquid concentrate or stable liquid dispersion is defined as one that does not undergo phase separation or increase or decrease in viscosity by more than about 10% after 4 weeks of storage at 4°C and 40°C. Desirably, concentrated liquid compositions and diluted liquid dispersions are also room-temperature stable. As used herein, "room-temperature stable" refers to a composition that does not undergo phase separation or increase or decrease in viscosity by more than about 10% after 52 weeks of storage at temperatures likely to be encountered on retail shelves, e.g., temperatures ranging from about 19°C to about 30°C.

[0046] Product Uses The concentrated liquid fabric softening compositions of the present technology can be used, for example, as concentrated liquid fabric softening compositions in the rinse cycle of a domestic washing machine. The concentrated liquid fabric softening composition can be added directly, undiluted, through a dispenser drawer, or, for top-load washing machines, directly into the drum. The amount of concentrated fabric softener added to a washing machine can be sufficient to deliver about 1.5 g to about 8 g of esterquat actives per wash load. Such an amount typically provides about 0.04% to about 0.3% by weight of esterquat actives based on the weight of dry fabrics. For example, to deliver 0.15% active esterquats by weight of dry fabrics (WOF), a 50% active esterquat formulation would be dosed at 8.16 g for a 6-pound (2721.55 g) dry wash load: (0.15% WOF) (2721.55 g) / 50% = 8.16 g. where WOF represents the weight of dry fabric. The 0.15% WOF is based on the dosage of a commercial premium fabric softener for a medium load, according to the bottle instructions.

[0047] In some embodiments, the concentrated fabric softening composition may be added to a washing machine as a liquid. In other embodiments, the composition may be formulated as a fabric softening product, such as, but not limited to, a pod, packet, pouch, or capsule. The fabric softening product has a water-soluble or water-rupturable coating or film that encapsulates or contains a unit dose of the concentrated fabric softening composition. As used herein, the term "unit dose" refers to a pre-measured amount of fabric softening composition to be delivered to a minimum amount of laundry in a minimum volume of laundry. For large amounts of laundry, multiple doses may be required to achieve an effective amount of softening agent. Water-soluble or water-rupturable coatings or films are known in the art. Suitable materials for coatings or films include, but are not limited to, polyvinyl alcohol, polyvinylpyrrolidone, methylcellulose, hydroxymethylcellulose, partially hydrolyzed vinyl acetate, gelatin, and combinations thereof.

[0048] Alternatively, the concentrated liquid fabric softening composition may be diluted prior to use, preferably with water, to a concentration of about 2% to about 22%, preferably about 3% to about 8%, by weight of esterquat actives, based on the total weight of the diluted composition. Some embodiments of the concentrated fabric softening composition are easily dispersible, allowing dilution to be performed by the consumer or by consumer product manufacturers who do not have the high shear mixing equipment or specialized equipment often used to make traditional liposomal softener dispersions.

[0049] The fabric softening composition (either concentrated or diluted) is added to the dispenser in an effective amount to soften and condition fabrics under predetermined washing conditions. The fabric softening composition can also be used in hand wash processes, where the fabric softening composition is added to one or more rinse bath solutions for manual fabric rinsing in a hand wash process. Alternatively, the composition may be used in commercial automatic laundry operations.

[0050] The following examples more fully illustrate embodiments of the present technology. All parts, percentages and proportions referred to in this specification and the appended claims are by weight unless otherwise specified. Physical testing methods are described below. [Example]

[0051] Example 1 Esterquat was prepared as follows: Canola fatty acids (283 g / mol, 2876.0 g, 10.1625 mol) and antioxidant 1010 (1178 g / mol, 3.7 g, 0.003 mol) were added to a 5 L reactor equipped with mechanical stirring, nitrogen sparge, and distillation capability. The iodine value of this fatty acid is 111. Agitation was started, the contents were heated to 35°C, and triethanolamine (149 g / mol, 977.03 g, 6.5572 mol) was added. The ratio of fatty acid to TEA in this mixture was 1.55:1. The reaction temperature was increased to 190°C and held for 3.5 hours. After 3.5 hours, the reactor was cooled, and the esteramine intermediate was transferred for quaternization and tested (free amine = 1.77 meq / g, total acidity = 0.06 meq / g).

[0052] The esteramine intermediate (564 g / mol, 3650.3 g, 6.5 mol) was added to a 5 L reactor equipped with mechanical stirring, a nitrogen headspace sweep, and reflux capability. The stirring and nitrogen sweep were initiated. The reaction temperature was adjusted to 50°C, and dimethyl sulfate (126 g / mol, 774.8 g, 6.1 mol) was added dropwise over 1 hour. The temperature was controlled at a maximum of 85°C during the addition. The reaction was mixed at 85°C for 1 hour. Sodium chlorite, 25% by weight (90.4 g / mol, 9.8 g, 0.03 mol) was added and mixed for 30 minutes. The product was recovered and tested (free amine = 0.08 meq / g, cationic activity = 1.17 meq / g, total acidity = 0.10 meq / g, Gardner color = 4.6). A slightly yellow paste was obtained. This esterquat is designated EQ1.

[0053] Example 2 Canola fatty acids (283 g / mol, 647.8 g, 2.289 mol), triethanolamine (149 g / mol, 171.0 g, 1.1477 mol), and antioxidant 1010 (1178 g / mol, 0.82 g, 0.001 mol) were added to a 2-L reactor equipped with mechanical stirring, a nitrogen subsurface sparge, and distillation capability. The iodine value of the fatty acid was 111, and the fatty acid to TEA ratio was 2.00:1. Agitation was started, and the contents were heated to 75°C. The nitrogen sparge was started. The reaction temperature was then increased to 190°C and held for 4.5 hours. After 4.5 hours, the reactor was cooled, and the esteramine intermediate was transferred for quaternization and tested (free amine = 1.48 meq / g, total acidity = 0.05 meq / g).

[0054] The esteramine intermediate (675 g / mol, 753.7 g, 1.1 mol) was added to a 2 L reactor equipped with mechanical stirring, a nitrogen headspace sweep, and reflux capability. The stirring and nitrogen sweep were started. The reaction temperature was adjusted to 45°C. Dimethyl sulfate (126 g / mol, 130.5 g, 1.0 mol) was added dropwise over 1 hour. The temperature was controlled to a maximum of 85°C during the addition. The reaction was mixed at 85°C for 1 hour. The product was collected and tested (free amine = 0.09 meq / g, cationic activity = 1.16 meq / g, total acidity = 0.01 meq / g). A slightly yellow paste was obtained. This esterquat is designated EQ2.

[0055] Example 3 Distilled tallow fatty acids (272 g / mol, 1067.05 g, 3.9230 mol) and hydrogenated tallow fatty acids (272 g / mol, 409.89 g, 1.5069 mol) were added to a 3 L reactor equipped with mechanical stirring, a nitrogen subsurface sparge, and distillation capability. The iodine value of this fatty acid mixture is approximately 34. Agitation was started, and the contents were heated to 75°C. Triethanolamine (149 g / mol, 521.3 g, 3.4987 mol), Antioxidant 1010 (1178 g / mol, 2.0 g, 0.002 mol), and phosphoric acid (82 g / mol, 1.0 g, 0.01 mol) were added. The fatty acid to TEA ratio was 1.55:1. Nitrogen sparging was started. The reaction temperature was then increased to 190°C and held for 4 hours. After 4 hours, the reactor was cooled and the ester amine intermediate was transferred for quaternization and tested (free amine = 1.81 meq / g, total acidity = 0.06 meq / g).

[0056] The ester amine intermediate (552 g / mol, 1836.0 g, 3.3 mol) was added to a 3 L reactor equipped with mechanical stirring, a nitrogen headspace sweep, and reflux capability. The stirring and nitrogen sweep were started. The reaction temperature was adjusted to 45°C. Dimethyl sulfate (126 g / mol, 381.8 g, 3.0 mol) was added dropwise over 30 minutes. The temperature was controlled at a maximum of 85°C during the addition. The reaction was mixed at 85°C for 1 hour. Dimethyl sulfate (126 g / mol, 20.0 g, 0.2 mol) was added dropwise. The temperature was controlled at a maximum of 85°C during the addition. The reaction was mixed at 85°C for 1 hour. The product was recovered and tested (free amine = 0.08 meq / g, cationic activity = 1.16 meq / g, total acidity = 0.17 meq / g). A waxy solid was obtained. This esterquat is designated EQ3.

[0057] Example 4 1,3-Diethoxy-2-propanol (DEP) with 100% BCI can be synthesized by at least two methods. One method involves reacting sodium ethoxide with 1,3-dichloro-2-propanol (dichlorohydrin) using ethanol as the solvent, as reported in Wills, et al. J. Chem. Soc., Perkins Trans. I 2002, 965-981. DOI: 10.1039 / b111097g. The reaction mixture is diluted with water to dissolve the precipitated sodium chloride, followed by extraction and column chromatography to obtain the product in moderate yield. Scheme 1 below illustrates the described chemical method. A modified version of this method was used to synthesize the DEP used in the examples. Specifically, column chromatography was avoided by filtering the reaction mixture, followed by distillation as the preferred method of separation and purification. [ka]

[0058] A second method for producing DEP with 100% BCI involves the reaction of sodium ethoxide with epichlorohydrin, as described in Garcia, et al. Green Chem. 2010, 12, 426-434. DOI: 10.1039 / b92331g. In this case, epichlorohydrin is added in a controlled manner to an ethanol solution of sodium ethoxide. The first step of the reaction is the action of sodium ethoxide on the epoxide ring, which opens the ring, which then spontaneously closes on the other side to produce an ethoxy-substituted epoxide. A second mole of sodium ethoxide is then reacted with the newly formed epoxide ring to produce deprotonated diethoxy-2-propanol with a sodium counterion. The deprotonated diethoxy-2-propanol then removes a proton from the ethanol solvent to produce the desired product and one mole of sodium ethoxide. Overall, two moles of sodium ethoxide reacting with epichlorohydrin produces only one mole of sodium chloride. When the reaction is deemed complete, the reaction mixture is diluted with water and concentrated to remove volatiles, and the product is then isolated in high yield by column chromatography. Alternatively, column chromatography can be avoided by using distillation as a means of product isolation. The described chemical method is shown in Scheme 2. [ka] Scheme 2 is preferred because it produces only one mole of sodium chloride, whereas Scheme 1 produces two moles of sodium chloride.

[0059] To be a 100% BCI version of DEP, the feedstocks employed must be naturally derived. While ethanol is commercially available as a grain-based product, both 1,3-dichlorohydrin and epichlorohydrin can be obtained using the Dow Chemical Company's glycerin to epichlorohydrin (GTE) process, which is described in Bell, et al., Clean 2008, 36(8), 657-661. DOI: 10.1002 / clen.200800067. The GTE process uses vegetable glycerin as a starting material, allowing for the production of biorenewable 1,3-dichlorohydrin and epichlorohydrin with 100% BCI content.

[0060] The formulations in the following examples were made by adding the solvent and water to a beaker, followed by the esterquat. The mixture was then mixed for several minutes in an Ika benchtop mixer. The ingredients used in making the formulations containing EQ1 were prepared at room temperature. None of the ingredients used to make the EQ1 formulations were heated before adding them to the beaker, nor were they heated while the batch was being mixed. All formulations had a pH between 2.5 and 4.0. The pH was adjusted as necessary to obtain formulations with a pH between 2.5 and 4.0.

[0061] Concentrated formulations designated as clear or transparent in the following examples have a light transmittance of greater than about 50 at a wavelength of 420 nanometers using a 1-centimeter cuvette, where the composition is measured at 25°C in the absence of dyes and opacifiers. Alternatively, a composition's transparency may be measured as having an absorbance (A) of less than about 0.3 at 420 nanometers, which is equivalent to a percent transmittance of greater than about 50 using the same cuvette. The relationship between absorbance and transmittance is as follows: transmittance = 100 (1 / antilog A). A formulation designated as unstable means either that the transmittance at 420 nm was less than 50% and / or that the formulation was phase separated. "Phase separated" means that the separated phases could be visually detected. Unless otherwise indicated, viscosity measurements were performed at room temperature (25°C) using a Brookfield DV-II+ viscometer at 50 RPM with an RVT spindle 4. Sample size was approximately 100 g in a 4 oz (approximately 113 gram) jar.

[0062] Example 5 In this example, formulations were made to evaluate the dispersibility of the formulations in water. Each formulation contained 50% by weight of EQ1 as the esterquat, 30% by weight of solvent, and 20% by weight of water. The formulations varied in the ratio of dimethyl lauramide / myristamide (CAA) and polyethylene glycol 200 (PEG200) in the solvent. The formulations are shown in Table 1 below. The dispersibility of each formulation in water was determined by the following test: 1 gram of the formulation was added to an 8-ounce (approximately 227 gram) bottle containing 120 ml of water, the cap was placed on, and the mixture was vigorously shaken 10 times by hand. A formulation was considered easily dispersible if there were no visible particles after shaking. The results are shown in Table 1. Unless otherwise noted below, all stable formulations were easily dispersible in water. Even formulations that are found to be stable but have visible particles and are deemed not to be easily dispersible may be useful for making dilute formulations in manufacturing sites that lack the equipment to make traditional liposomal dispersions but have mixing capabilities. The visible suspended particles in the not easily dispersible formulations will eventually disperse with more mixing than was done in the dispersibility test. [Table 1]

[0063] The results in Table 1 show that when CAA or PEG200 was used as the sole solvent, formulations were not stable at a 50 wt% esterquat concentration. Similarly, formulations were not stable when the CAA to PEG200 ratio was 5:1 or 1:5. However, all formulations with CAA to PEG200 ratios ranging from 2:1 to 1:2 were stable. The results indicate that formulation stability may depend on the ratio of solvents in the solvent mixture. The results also show that a mixture of solvents can provide formulation stability, whereas the same solvents used individually can result in unstable formulations.

[0064] Example 6 This example evaluates the softening ability of a formulation according to the present invention compared to a conventional esterquat dispersion. The formulation in Example 5, containing 15% CAA and 15% PEG, was also used in this example. This formulation was dispersed in water to produce a dispersion containing 5% by weight of the esterquat active. A conventional liposome dispersion containing 5% by weight of EQ1 was used as a comparison. The conventional liposome dispersion was prepared by slowly adding EQ1 to an appropriate amount of water with stirring over a period of approximately 3-10 minutes, heating as necessary to improve mixing and promote liposome formation, and then continuing mixing for an additional approximately 5-15 minutes after all of the EQ1 had been added. Liposomes formed during the mixing process, resulting in a 5% by weight EQ1 liposome dispersion. The softening test method used was based on ASTM D-5237. White hand towels made from an 86 / 14 cotton / polyester blend were first subjected to a pre-wash process to remove all factory finish. For each test, 160 towels were washed in a conventional home washing machine. An experimental fabric softener sample was dosed into the washing machine during the rinse cycle. The towels were then tumble dried and allowed to equilibrate to room temperature overnight. Panelists then blindly evaluated pairs of towels via a paired comparison panel test. Votes were tallied for each sample. Using a one-sided directional difference test (Meilgaard, MC, Civil, GV, Carr, BT, Sensory Evaluation Techniques, 3rd Ed., CRC Press, 1999, pp. 277-278, 355, 371), a product must be selected at least 91 times in a 160-vote observational test to be considered statistically superior to the other at a 95% confidence level.

[0065] Using this assay, a 5% aqueous dispersion of the esterquat actives of the Example 5 formulation, containing 15% CAA and 15% PEG 200, was comparable to the softening of a conventional liposomal dispersion of 5% EQ1 esterquat actives. A 5% dispersion of the Example 5 formulation was easily made by gently mixing the concentrated formulation with water.

[0066] Example 7 Example 5 was repeated, except that EQ2 was used as the esterquat in each formulation. EQ1 and EQ2 differ in that EQ2 has a fatty acid to TEA ratio of 2.00:1, while EQ1 has a ratio of 1.55:1. The formulations and results are shown in Table 2. [Table 2]

[0067] Table 2 shows that all formulations were unstable, suggesting that formulation stability may be affected by the ratio of fatty acid to TEA used in making the esterquat. When using the PEG 200 / CAA solvent system and the canola fatty acid-based esterquat (TEA / DMS), the results indicate that the fatty acid to TEA ratio must be less than 2.0 to obtain a stable dispersion.

[0068] Example 8 Example 5 was repeated using only the stable formulations of Example 5 and substituting EQ3 as the esterquat in each formulation. EQ3 is made from a tallow fatty acid feedstock with an iodine value of 34, rather than the canola fatty acid feedstock used to make EQ1. The formulations and results are shown in Table 3. [Table 3]

[0069] Table 3 shows that the formulations were unstable, suggesting that formulation stability may also be affected by the iodine value of the fatty acid feedstock used in making the esterquat. When using a PEG 200 / CAA solvent system, the results indicate that the iodine value of the feedstock used to make the esterquat must be higher than 34 to obtain a stable dispersion.

[0070] Example 9 Using a series of different solvents according to the method described in the book "Soluble Science, Principles and Practice," Steven Abbott, 2017, Creative Commons NY-BD, the Hansen polarity parameter of EQ1 was determined to be 10.9, while the Hansen polarity parameter of EQ3 was determined to be 4.4. The Hansen solubility parameter is a physicochemical parameter that can be used to predict the behavior of a given solvent or solute. These results indicate that when using the PEG 200 / CAA solvent system, the Hansen solubility parameter of EQ should be higher than approximately 5.

[0071] Example 10 In this example, formulations were prepared with various amounts of esterquat to evaluate the effect of esterquat concentration on formulation stability. The formulations and results are shown in Table 4. [Table 4]

[0072] As shown in Table 4, at an esterquat concentration of 80 wt%, EQ1 with the PEG 200 / CAA solvent system is unstable. The results indicate that to obtain a stable composition, the upper limit of esterquat in this composition must be less than 80 wt%. The 60% and 70% formulations in this example were stable but did not readily disperse in water.

[0073] Example 11 A formulation containing 50% EQ1 / 20% dipropylene glycol monomethyl ether (DPM) / 10% CAA / 20% water was found to be clear, stable, and dispersible in water. The formulation also removed completely from the fabric softener dispenser drawer in a front-loading washing machine when a normal cycle was run. The BCI of this solvent system made from DPM and CAA is calculated as follows:

[0074] Total contribution of carbon atoms from DPM = (weight factor 2) x (148.2 g / mol) x (6.022 x 10 23 molecule / mol)X(7 carbon atoms / molecule)=1.249×10 27 Carbon atoms All of which come from non-bio-renewable sources.

[0075] Total contribution of carbon atoms from CAA = (weight factor 1) × (234 g / mol) × (6.022 × 10 23 molecules / mol) × (14.5 carbon atoms / mol) = 2.043 × 10 27 Of the carbon atoms, 86.2% come from biorenewable sources. This means that the number of biorenewable carbon atoms from CAA is 1.761 x 10 27 (2.043×10 27 × 0.862), and the number of non-bio-renewable carbons is 2.820 × 10 26 (2.043×10 27 × 0.138).

[0076] The total number of carbon atoms is 3.292 x 10 27 and the BCI of the solvent system is: BCI = 100 × [(1.761 × 10 27 ) / (3.292×10 27 )]=53.5

[0077] Example 12 In this example, the effect of varying the amount of solvent in the solvent system was evaluated. The following formulations were prepared: 50% EQ1 / 15% dipropylene glycol monomethyl ether (DPM) / 15% CAA / 20% water, and 50% EQ1 / 10% dipropylene glycol monomethyl ether (DPM) / 20% CAA / 20% water. The solvent concentration was the same at 30%, but the amounts of DPM and CAA solvents were varied. Despite the same solvent components and total amount of solvent as used in Example 11, the formulations were found to be unstable. These results indicate that the relative amount of solvent in the solvent system affects the stability of the composition. The calculated BCI values ​​for the solvent system (DPM + CAA) for each of these formulations are 66.0 and 74.8, respectively.

[0078] Example 13 A formulation containing 80% EQ1 / 20% 1,3-diethoxy-2-propanol (DEP) was found to be clear, stable, and dispersible in water. The formulation also completely removed from the fabric softener dispenser drawer in a front-loading washing machine when run through a normal cycle. DEP has a BCI of 100. This example demonstrates that a concentrated fabric softening composition of the present technology can be prepared without water.

[0079] Example 14 A freeze / thaw stability comparison was performed on two formulations, each containing 5% EQ1. The first was made via a traditional liposome method, and the second was made by diluting a concentrated formulation containing 50% EQ1, 15% bio-based PEG-200, 15% NINOL® CAA, and 20% water. The freeze / thaw stability test method used was as follows: 1. Prepare the sample and transfer it to a storage container (e.g., a 4 oz. jar) 2. Place the sample in a -15°C freezer. 3. Leave the sample at -15°C for 24 hours. After 24 hours, remove the samples from the -15°C freezer and place them at room temperature. 5. Allow the sample to thaw until it reaches room temperature (usually 6 hours is sufficient). 6. Perform a visual inspection of the sample for phase separation, thickening / gelling, and non-uniformity / clumping If three freeze / thaw cycles are performed, repeat this procedure three times.

[0080] While formulations made by the traditional liposome route thickened and clumped / non-uniform after one freeze / thaw cycle, 5% formulations made by diluting a 50% concentrate maintained the same viscosity and were uniform / non-clumped after three freeze / thaw cycles. Traditional liposomes fail freeze / thaw cycles because they "crack" during the freezing process. When liposomes crack, their hydrophobic surfaces are exposed, but it is undesirable for the hydrophobic surface to be exposed to the aqueous phase. Upon thawing, their hydrophobic surfaces are attracted to each other but stick to each other in a random interliposomal manner (i.e., not simply recombined within the liposome in an orderly fashion as in cracked liposomes), forming large particles and resulting in macroscopic thickening and clumping. Without being bound by theory, it is possible that non-liposomal structures form when a 5% dispersion is made by diluting a 50% concentrate. The presence of PEG-200 and NINOL® CAA may contribute to non-liposomal droplet formation. Alternatively, without wishing to be bound by theory, the presence of PEG-200 and / or NINOL® CAA may alter the properties of liposomes, if present, so that they do not crack catastrophically upon freezing.

[0081] Example 15 The hydrolysis of ester bonds in two formulations containing EQ1 at elevated storage temperatures (50°C) was followed by NMR. The first was a concentrated formulation containing 50% EQ1, 15% bio-based PEG-200, 15% NINOL® CAA, and 20% water. The second was a 5% active EQ1 dispersion made by a conventional liposome method. Percentages were normalized so that the sum of TEA quats (no ester bonds), monoester quats (one ester bond), diester quats (two ester bonds), and triester quats (three ester bonds) by weight equaled 100%. After 9 weeks, the normalized weight percentage of TEA quats (no ester bonds, the final product formed in the hydrolysis process) in the concentrated formulation was 8.2%, compared with 20.2% in the conventional 5% formulation. This indicates that the rate of hydrolysis in the concentrate is slower than half, which means that the shelf life should be longer than that of conventional liposomal dispersions.

[0082] Example 16 A formulation was made utilizing 70% by weight EQ1 and 30% by weight CAA. The formulation was stable and readily water-dispersible. This result was unexpected, considering that a formulation with a lower concentration of the same quat actives was unstable when 30% by weight CAA was used as the sole solvent (Example 5, Table 1, 50% EQ1 / 30% CAA / 20% water formulation). That a formulation containing the same concentration of the same solvent but a higher concentration of quat actives could be stable is surprising, given that the lower concentration quat formulation was not stable.

[0083] Example 17 Formulations similar to that of Example 16 were made using either M-10 or M-8-10 in place of CAA, and these formulations were also stable and easily dispersed.

[0084] Example 18 Additional formulations that were found to be stable and easily dispersible are shown in Table 5. [Table 5] The results from Examples 16-18 indicate that stable, highly concentrated (70-80 wt% active esterquat) compositions can be prepared using solvent systems containing fatty acid amides alone or in combination with polyethylene glycol.

[0085] The present technology is described herein in such full, clear, and concise terms as to enable any person skilled in the relevant art to practice the present technology. It is to be understood that the foregoing describes preferred embodiments of the present technology, and that modifications may be made therein without departing from the spirit or scope of the present technology as set forth in the appended claims. Moreover, the present examples are provided by way of illustration, not exhaustive, of some embodiments within the scope of the claims.

Claims

1. A clear, stable liquid composition comprising: (A) 30% to 75% by weight, based on the weight of the composition, of one or more esterquats; the one or more esterquats are quaternized reaction products of a fatty acyl source having an iodine value of 40 to 130 and triethanolamine (TEA) in a molar ratio of fatty acyl to alkanolamine of 1.3:1 to 1.8:1, or a methyldiethanolamine (MDEA) in a molar ratio of fatty acyl to alkanolamine of 1.0:1 to 2.0:1; (B) 20% to 50% by weight, based on the weight of the composition, of a solvent system, the solvent system being a mixture of one or more polyethylene glycols having a number average molecular weight of 130 to 700 and one or more fatty acid amides having the general structure: 【Chemistry 1】 wherein R has 6 to 20 carbon atoms, is branched or linear, is saturated or has one or more double bonds, and optionally contains one or more hydroxyl groups; and R １ and R ２ are independently hydrogen, a C1-C6 alkyl group, or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; a solvent system, wherein the polyethylene glycol and the fatty acid amide are present in the mixture in a weight ratio of 3:1 to 1:3; (C) optionally, from 0% to a maximum of 30% by weight of water; A composition having a measured viscosity of less than 5000 cP at 25°C.

2. A clear, stable liquid composition comprising: (A) 30% to 90% by weight, based on the weight of the composition, of one or more esterquats, the one or more esterquats being the quaternized reaction product of a fatty acyl source having an iodine value of 40 to 130 reacted with triethanolamine in a molar ratio of fatty acyl to alkanolamine of 1.3:1 to 1.8:1, or methyldiethanolamine in a molar ratio of fatty acyl to alkanolamine of 1.0:1 to 2.0:1; (B) 10% to 50% by weight, based on the weight of the composition, of a solvent system, the solvent system being one or more 1,3-dialkoxy-2-propanols having the general formula: 【Chemistry 2】 In the formula, R ａ and R ｂ are independently a C1-C6 alkyl group or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; a solvent system; (C) optionally, from 0% to a maximum of 30% by weight of water; A composition having a measured viscosity of less than 5000 cP at 25°C.

3. A clear, stable liquid composition comprising: (A) 30% to 90% by weight, based on the weight of the composition, of one or more esterquats, the one or more esterquats being the quaternized reaction product of a fatty acyl source having an iodine value of 40 to 130 reacted with triethanolamine in a molar ratio of fatty acyl to alkanolamine of 1.3:1 to 1.8:1, or methyldiethanolamine in a molar ratio of fatty acyl to alkanolamine of 1.0:1 to 2.0:1; (B) 10% to 50% by weight, based on the weight of the composition, of a solvent system comprising (i) one or more glycol ethers selected from the group consisting of 2-butoxyethanol, 2-phenoxyethanol, 2-benzyloxyethanol, 2(2-methoxyethoxy)ethanol, 2(2-ethoxyethoxy)ethanol, dipropylene glycol monomethyl ether, dibutoxyethane, and combinations thereof, in admixture with (ii) one or more fatty acid amides having the general structure: 【Transformation 3】 wherein R has 6 to 20 carbon atoms, is branched or linear, is saturated or has an unsaturated double bond, and optionally contains one or more hydroxyl groups; and R １ and R ２ are independently hydrogen, a C1-C6 alkyl group, or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; a solvent system, wherein the glycol ether and the fatty acid amide are present in the mixture in a weight ratio of 2:1; (C) optionally, from 0% to a maximum of 30% by weight of water; A composition having a measured viscosity of less than 5000 cP at 25°C.

4. A clear, stable liquid composition comprising: (A) 55% to 85% by weight, based on the weight of the composition, of one or more esterquats, the one or more esterquats being the quaternized reaction product of a fatty acyl source having an iodine value of 40 to 130 with triethanolamine in a molar ratio of fatty acyl to alkanolamine of 1.3:1 to 1.8:1, or with methyldiethanolamine in a molar ratio of fatty acyl to alkanolamine of 1.0:1 to 2.0:1; (B) 15% to 45% by weight of the composition of a solvent system, the solvent system being one or more fatty acid amides having the general structure: 【Chemistry 4】 wherein R has 6 to 20 carbon atoms, is branched or linear, is saturated or has one or more double bonds, and optionally contains one or more hydroxyl groups; and R １ and R ２ are independently hydrogen, a C1-C6 alkyl group, or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; and (C) optionally, from 0% to a maximum of 10% by weight of water; A composition having a measured viscosity of less than 5000 cP at 25°C.

5. 5. The composition of any one of claims 1 to 4, wherein the fatty acyl source is derived from sunflower oil, canola oil, corn oil, cottonseed oil, linseed oil, peanut oil, meadowfoam oil, soybean oil, walnut oil, jojoba oil, palm oil, borage oil, safflower oil or rapeseed oil, or a mixture thereof.

6. 10. The composition of claim 1, wherein the polyethylene glycol comprises polyethylene glycol 200 (PEG200).

7. 5. The composition of any one of claims 1, 3 and 4, wherein the fatty acid amide comprises dimethyl lauramide / dimethyl myristamide.

8. 7. The composition of claim 6, wherein the fatty acid amide comprises dimethyl lauramide / dimethyl myristamide, and wherein PEG 200 and dimethyl lauramide / dimethyl myristamide are present in the mixture in a weight ratio of 1:2 to 2:

1.

9. 10. The composition of claim 1, wherein the esterquat comprises 50% by weight and the solvent system comprises 30% by weight, based on the weight of the composition.

10. A fabric softener composition comprising water and the clear, stable liquid composition of any one of claims 1 to 4, wherein the one or more esterquats are present in the fabric softener composition in an amount ranging from 2 to 22 weight percent.

11. 11. The softener composition of claim 10, further comprising at least one ionizable salt.

12. 1. A method of making a softener composition, comprising: (A) providing a concentrated fabric softening composition, the concentrated fabric softening composition comprising: (i) 30% to 75% by weight, based on the weight of the concentrated fabric softening composition, of one or more esterquats, the one or more esterquats comprising: one or more esterquats that are quaternized reaction products of a fatty acyl source having an iodine value of 40 to 130 with triethanolamine in a molar ratio of fatty acyl to alkanolamine of 1.3:1 to 1.8:1, or with methyldiethanolamine in a molar ratio of fatty acyl to alkanolamine of 1.0:1 to 2.0:1; (ii) 20% to 50% by weight of a solvent system, based on the weight of the concentrated fabric softening composition, the solvent system being a mixture of one or more polyethylene glycols having a number average molecular weight of 130 to 700 and one or more fatty acid amides having the general structure: 【Transformation 5】 wherein R has 6 to 20 carbon atoms, is branched or linear, is saturated or has an unsaturated double bond, and optionally contains one or more hydroxyl groups; and R １ and R ２ are independently hydrogen, a C1-C6 alkyl group, or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; a solvent system, wherein the polyethylene glycol and the fatty acid amide are present in the mixture in a weight ratio of 3:1 to 1:3; and (iii) optionally, from 0% to a maximum of 30% by weight of water; providing a concentrated fabric softening composition having a measured viscosity of less than 5000 cP at 25°C; and (B) mixing the concentrated fabric softening composition in water to form a stable aqueous dispersion comprising 2% to 22% by weight of the esterquat, based on the total weight of the dispersion, thereby making the softener composition.

13. 1. A method of making a softener composition, comprising: (A) providing a concentrated fabric softening composition, the concentrated fabric softening composition comprising: (i) 30% to 90% by weight, based on the weight of the composition, of one or more esterquats, the one or more esterquats being the quaternized reaction product of a fatty acyl source having an iodine value of 40 to 130 with triethanolamine in a molar ratio of fatty acyl to alkanolamine of 1.3:1 to 1.8:1, or methyldiethanolamine in a molar ratio of fatty acyl to alkanolamine of 1.0:1 to 2.0:1; and (ii) 10% to 50% by weight, based on the weight of the composition, of a solvent system, the solvent system being one or more 1,3-dialkoxy-2-propanol having the general formula: 【Transformation 6】 In the formula, R ａ and R ｂ are independently a C1-C6 alkyl group or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; and (iii) optionally, from 0% to a maximum of 30% by weight of water; providing a composition having a measured viscosity of less than 5000 cP at 25°C; and (B) mixing the concentrated fabric softening composition in water to form a stable aqueous dispersion comprising 2% to 22% by weight of the esterquat, based on the total weight of the dispersion, thereby making the softener composition.

14. 1. A method of making a softener composition, comprising: (A) providing a concentrated fabric softening composition, the concentrated fabric softening composition comprising: (i) 30% to 90% by weight, based on the weight of the concentrated fabric softening composition, of one or more esterquats, the one or more esterquats being the quaternized reaction product of a fatty acyl source having an iodine value of 40 to 130 with triethanolamine in a fatty acyl to alkanolamine molar ratio of 1.3:1 to 1.8:1, or methyldiethanolamine in a fatty acyl to alkanolamine molar ratio of 1.0:1 to 2.0:1; (ii) 10% to 50% by weight of a solvent system, based on the weight of the concentrated fabric softening composition, the solvent system being a mixture of one or more glycol ethers selected from the group consisting of 2-butoxyethanol, 2-phenoxyethanol, 2-benzyloxyethanol, 2(2-methoxyethoxy)ethanol, 2(2-ethoxyethoxy)ethanol, dipropylene glycol monomethyl ether, dibutoxyethane, and combinations thereof, and one or more fatty acid amides having the general structure: 【Transformation 7】 wherein R has 6 to 20 carbon atoms, is branched or linear, is saturated or has an unsaturated double bond, and optionally contains one or more hydroxyl groups; and R １ and R ２ are independently hydrogen, a C1-C6 alkyl group, or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; a solvent system, wherein the glycol ether and the fatty acid amide are present in the mixture in a weight ratio of 2:1; and (iii) optionally, from 0% to a maximum of 30% by weight of water; providing a concentrated fabric softening composition having a measured viscosity of less than 5000 cP at 25°C; and (B) mixing the concentrated fabric softening composition in water to form a stable aqueous dispersion comprising 2% to 22% by weight of the esterquat, based on the total weight of the dispersion, thereby making the softener composition.

15. 1. A method of making a softener composition, comprising: (A) providing a concentrated fabric softening composition, the concentrated fabric softening composition comprising: (i) about 55% to about 85% by weight, based on the weight of the composition, of one or more esterquats, the one or more esterquats being the quaternized reaction product of a fatty acyl source having an iodine value of 40 to 130 with triethanolamine in a molar ratio of fatty acyl to alkanolamine of 1.3:1 to 1.8:1, or methyldiethanolamine in a molar ratio of fatty acyl to alkanolamine of 1.0:1 to 2.0:1; (ii) about 15% to about 45% by weight of the composition of a solvent system, the solvent system being one or more fatty acid amides having the general structure: 【Transformation 8】 wherein R has 6 to 20 carbon atoms, is branched or linear, is saturated or has one or more double bonds, and optionally contains one or more hydroxyl groups; and R １ and R ２ are independently hydrogen, a C1-C6 alkyl group, or a C2-C6 alkenyl group, optionally containing one or more hydroxyl groups, and, if three or more carbon atoms are present, optionally branched; a solvent system; (iii) optionally, from 0% to a maximum of 10% by weight of water; providing a composition having a measured viscosity of less than 5000 cP at 25°C; and (B) mixing the concentrated fabric softening composition in water to form a stable aqueous dispersion comprising 2% to 22% by weight of the esterquat, based on the total weight of the dispersion, thereby making the softener composition.

16. The method of any one of claims 12 to 15, further comprising the step of adding an ionizable salt.

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