Concentrated liquid ester quaternary ammonium salt composition

Abstract

A transparent, stable concentrated liquid composition is disclosed, which contains 30% to 90% by weight of an ester quaternary ammonium salt active agent and 10% to 50% by weight of a specific solvent system. The ester quaternary ammonium salt active agent is a quaternary ammonium reaction product of a fatty acyl source having an iodine value of 40 to 130 and an alkanolamine at a fatty acyl:alkanolamine molar ratio of 1.0:1 to 2.2:1. The concentrated liquid 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 concentrated liquid composition can be easily diluted in water to form a stable aqueous dispersion.

Description

Technical Field

[0001] The present technology relates to transparent concentrated esterquat compositions that are chemically stable, storage stable, and employ esterquat active agents that are biodegradable and water dispersible in the compositions. The concentrated liquid compositions can be used without dilution, or can be readily dispersed in water to form stable liquid dispersions. The concentrated liquid esterquat compositions are particularly useful in fabric softening applications. Background Art

[0002] Liquid fabric softening compositions that soften fabrics in the rinse cycle are known. Such compositions typically contain a softener active agent in an amount ranging from about 5% to about 15% by weight, with the remainder being primarily water. More concentrated compositions, i.e., concentrated compositions having an active dosage greater than 15%, are desirable because these compositions require less packaging and therefore have less environmental impact due to, for example, reduced shipping costs and less waste generated.

[0003] One problem associated with concentrated fabric softening compositions is that the product is unstable on storage, especially when stored at elevated temperatures or at refrigerated temperatures. Instability can manifest itself as a thickening of the product on storage, even to the point where the product is no longer pourable. As a result, typical commercially available liquid fabric softener compositions today have a softener active concentration of about 15% by weight or less.

[0004] Another problem with concentrated fabric softening compositions is that they generally require a solvent in order to achieve an acceptable concentrated aqueous dispersion. It is also generally necessary to add a solvent in order to have a product with a sufficiently low viscosity in the molten state to be able to be pumped with conventional equipment. The added solvent is generally a volatile organic compound (VOC) such as isopropyl alcohol or ethanol, which is undesirable from an environmental perspective. In addition, stricter regulations have been proposed to limit VOCs, making it important to limit or eliminate solvents that contribute to VOCs.

[0005] There is also a trend in the consumer product market to formulate products with ingredients based on renewable resources derived from plants or animals rather than fossil fuels. The ingredients are considered "green" or "natural" because they are derived from renewable sources and / or sustainable sources. Therefore, they are more environmentally friendly than ingredients derived from fossil fuels. Ingredients with a high Biorenewable Carbon Index (BCI), for example, greater than 80, indicate that the ingredients contain carbon derived primarily from plant-based, animal-based, or marine-based sources.

[0006] There is a need for highly concentrated fabric softener active systems that are stable during storage in concentrated form but can also be easily diluted in water at room temperature to form a stable fabric softening dispersion without gelling. There is also a need for stable concentrated liquid fabric softener compositions that have ingredients that can be made from renewable resources and do not require VOC solvents. Summary of the invention

[0007] In a first aspect, the present technology provides a clear, stable liquid composition comprising: (A) about 30% to about 80% by weight, based on the weight of the composition, of one or more esterquats, wherein the one or more esterquats are quaternized reaction products of a fatty acyl source having an iodine value of 40 to 130 and an alkanolamine at a fatty acyl:alkanolamine molar ratio 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, wherein the solvent system comprises (i) a mixture of one or more polyethylene glycols having a number average molecular weight between 130 and 700 and one or more fatty amides having the general structure

[0008]

[0009] wherein R has 6 to 20 carbon atoms, is branched or linear, saturated or has unsaturated double bonds, and optionally contains one or more hydroxyl groups (hydroxyl groups are -OH groups);

[0010] And R 1 and R 2 independently hydrogen, C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and optionally branched when there are 3 or more carbon atoms; and (C) optionally, 0 wt % to 30 wt % water; wherein the composition has a measured viscosity of less than 5000 cP at 25°C.

[0011] In another aspect, the present technology provides a clear, stable liquid composition comprising (A) from about 30% to about 90% by weight, based on the weight of the composition, of one or more esterquats, wherein the one or more esterquats are quaternized reaction products of a fatty acyl source having an iodine value of 40 to 130 and an alkanolamine at a fatty acyl:alkanolamine molar ratio of from about 1.0:1 to about 2.2:1; and (B) from 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 amides having the following general structure:

[0012]

[0013] wherein R has 6 to 20 carbon atoms, is branched or linear, saturated or has unsaturated double bonds, and optionally contains one or more hydroxyl groups;

[0014] And R 1 and R 2 independently hydrogen, C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and optionally branched when there are 3 or more carbon atoms; and (C) optionally, 0 wt % to 30 wt % water; wherein the composition has a measured viscosity of less than 5000 cP at 25°C.

[0015] In another aspect, the present technology provides a clear, stable composition comprising (A) from about 30% to about 90% by weight, based on the weight of the composition, of one or more esterquats, wherein the one or more esterquats are the quaternized reaction product of a fatty acyl source having an iodine value of 40 to 130 and an alkanolamine in a fatty acyl:alkanolamine molar ratio of from about 1.0:1 to about 2.2:1; and (B) from about 10% to about 50% by weight, based on the weight of the composition, of a solvent system, wherein the solvent system comprises one or more 1,3-dialkoxy-2-propanols having the general formula:

[0016]

[0017] Where R a and R b is independently C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and when there are 3 or more carbon atoms, may be optionally branched; and (C) optionally, 0 wt% to 30 wt% water;

[0018] wherein the composition has a measured viscosity of less than 5000 cP at 25°C.

[0019] In another aspect, the present technology provides a clear, stable composition comprising (A) from about 55 wt % to about 85 wt %, by weight of the composition, of one or more esterquats, wherein the one or more esterquats are the quaternized reaction product of a fatty acyl source having an iodine value of 40 to 130 and an alkanolamine in a fatty acyl:alkanolamine molar ratio of from about 1.0:1 to about 2.2:1; and (B) from about 15 wt % to about 45 wt %, by weight of the composition, of a solvent system comprising one or more fatty amides having the following general structure:

[0020]

[0021] wherein R has 6 to 20 carbon atoms, is branched or linear, saturated or has unsaturated double bonds, and optionally contains one or more hydroxyl groups;

[0022] And R 1 and R 2 independently hydrogen, C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and optionally branched when there are 3 or more carbon atoms; and (C) optionally, 0 wt % to 10 wt % water, wherein the composition has a measured viscosity of less than 5000 cP at 25°C.

[0023] In another aspect, the present technology is directed to a method of forming a fabric softener composition comprising the steps of: (A) providing a concentrated fabric softening composition, wherein the concentrated fabric softening composition comprises (i) from about 30% to about 80% by weight, based on the weight of the concentrated fabric softening composition, of one or more esterquat actives, wherein the one or more esterquat actives are the quaternization reaction product of a fatty acyl source having an iodine value of 40 to 130 and an alkanolamine at a fatty acyl:alkanolamine molar ratio of from about 1.0:1 to about 2.2:1; and (ii) from about 20% to about 50% by weight, based on the weight of the concentrated fabric softening composition, of a solvent system, wherein the solvent system comprises a mixture of one or more polyethylene glycols having a number average molecular weight between 130 and 700 and one or more fatty amides having the following general structure:

[0024]

[0025] wherein R has 6 to 20 carbon atoms, is branched or linear, saturated or has unsaturated double bonds, and optionally contains one or more hydroxyl groups;

[0026] And R 1 and R 2 independently hydrogen, C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and optionally branched when 3 or more carbon atoms are present; and (iii) optionally, 0 wt % 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, the stable aqueous dispersion comprising 2 wt % to 22 wt % esterquat active agent based on the total weight of the dispersion, thereby forming the fabric softener composition.

[0027] In still other aspects, the present technology provides a method of forming a fabric softener composition comprising the steps of: (A) providing a concentrated fabric softening composition, wherein the concentrated fabric softening composition comprises (i) from about 30% to about 90% by weight, based on the weight of the concentrated fabric softening composition, of one or more esterquat actives, wherein the one or more esterquat actives are the quaternization reaction product of a fatty acyl source having an iodine value of 40 to 130 and an alkanolamine at a fatty acyl:alkanolamine molar ratio of from about 1.0:1 to about 2.2:1; and (ii) from about 10% to about 50% by weight, based on the weight of the concentrated fabric softening composition, of a solvent system, wherein the solvent system comprises one or more 1,3-dialkoxy-2-propanols having the general formula:

[0028]

[0029] Where R a and R b is independently a C1 to C6 alkyl or a C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and may be optionally branched when 3 or more carbon atoms are present; and (C) optionally, 0 wt% 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, the stable aqueous dispersion comprising 2 wt% to 22 wt% esterquat active agent based on the total weight of the dispersion, thereby forming the fabric softener composition.

[0030] In still other aspects, the present technology provides a method of forming a fabric softener composition comprising the steps of: (A) providing a concentrated fabric softening composition, wherein the concentrated fabric softening composition comprises (i) from about 30% to about 90% by weight, based on the weight of the concentrated fabric softening composition, of one or more esterquat actives, wherein the one or more esterquat actives are the quaternization reaction product of a fatty acyl source having an iodine value of 40 to 130 and an alkanolamine at a fatty acyl:alkanolamine molar ratio of from about 1.0:1 to about 2.2:1; and (ii) from about 10% to about 50% by weight, based on the weight of the concentrated fabric softening composition, of a solvent system, wherein the solvent system comprises a mixture comprising 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 amides having the following general structure:

[0031]

[0032] wherein R has 6 to 20 carbon atoms, is branched or linear, saturated or has unsaturated double bonds, and optionally contains one or more hydroxyl groups;

[0033] And R 1 and R 2 is independently hydrogen, C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and may be optionally branched when 3 or more carbon atoms are present; and (C) optionally, 0 wt% to 30 wt% 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, the stable aqueous dispersion comprising 2 wt% to 22 wt% esterquat active agent based on the total weight of the dispersion, thereby forming the fabric softener composition.

[0034] In additional aspects, the present technology is directed to a method of forming a fabric softener composition comprising the steps of: (A) providing a concentrated fabric softening composition, wherein the concentrated fabric softening composition comprises (i) from about 55% to about 85% by weight, based on the weight of the concentrated fabric softening composition, of one or more esterquat actives, wherein the one or more esterquat actives are the quaternization reaction product of a fatty acyl source having an iodine value of 40 to 130 and an alkanolamine at a fatty acyl:alkanolamine molar ratio of from about 1.0:1 to about 2.2:1; and (ii) from 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 amides having the following general structure:

[0035]

[0036] wherein R has 6 to 20 carbon atoms, is branched or linear, saturated or has unsaturated double bonds, and optionally contains one or more hydroxyl groups;

[0037] And R 1 and R 2 independently hydrogen, C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and optionally branched when 3 or more carbon atoms are present; and (iii) optionally, 0 wt % to 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, the stable aqueous dispersion comprising 2 wt % to 22 wt % esterquat active agent based on the total weight of the dispersion, thereby forming the fabric softener composition. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] [not applicable] DETAILED DESCRIPTION

[0039] Although the technology described in the present invention will be described in conjunction with one or more preferred embodiments, it will be understood by those skilled in the art that the technology is not limited to those specific embodiments. On the contrary, the technology described in the present invention includes all alternatives, modifications and equivalents that can be included in the spirit and scope of the appended claims.

[0040] definition

[0041] The "Biorenewable Carbon Index" (BCI) refers to the calculation of the percentage of carbon derived from biorenewable resources and is calculated based on the number of biorenewable carbons divided by the total number of carbons in the entire molecule.

[0042] "Biorenewable" is defined herein as being derived from animal, plant or marine materials.

[0043] A "clear" or "transparent" composition is defined as a composition having a percent light transmittance greater than about 50 at a wavelength of 420 nanometers using a 1 centimeter cuvette, wherein the composition is measured at 25°C in the absence of dyes and opacifiers. Alternatively, the clarity of the composition can be measured as having an absorbance (A) of less than about 0.3 at 420 nanometers, which is equivalent to a percent transmittance greater than about 50 using the same cuvette as above. The relationship between absorbance and percent transmittance is:

[0044] Percent transmittance = 100 (1 / antilog A).

[0045] "VOC" refers to volatile organic compounds. These compounds have a vapor pressure greater than 2 mm Hg at 25°C, fewer than 7 carbon atoms, and a boiling point less than 120°C at atmospheric pressure.

[0046] Esterquaternary ammonium salt fabric softener compounds

[0047] The concentrated liquid composition of the present invention comprises an ester-based quaternary ammonium salt cationic material as a main active agent, and the ester-based quaternary ammonium salt cationic material is a quaternary ammonium reaction product of a fatty acyl source and an alkanolamine reaction. In general, the ester-based quaternary ammonium salt active agent of the present invention is prepared by combining a natural oil or other fatty acid source with an alkanolamine, usually at a starting temperature at which the natural oil or fatty acid source is liquid or melted, optionally adding a catalyst, and then heating the reaction mixture until the desired esteramine reaction product is obtained by verifying the acid value and basicity value. The fatty acid source and the alkanolamine are reacted with a fatty acyl group:alkanolamine molar ratio of about 1.0:1 to about 2.2:1 to form an esteramine intermediate. Subsequently, an alkylating agent is used to quaternize the esteramine intermediate, thereby producing an ester-based quaternary ammonium salt product. The alkylating agent used to prepare the ester-based quaternary ammonium salt is known in the art, and includes, 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 monoesters, diesters and triester components depending on the starting alkanolamine and optionally certain amounts of one or more reactants, intermediates and by-products including but not limited to free amine and free fatty acids or parent fatty acyl compounds or derivatives thereof.

[0048] The fatty acyl source for preparing the ester group quaternary ammonium salt can be various starting materials, such as free fatty acids, fatty acid esters or acyl chlorides corresponding to fatty acids. Free fatty acids can be individual, such as single purified fatty acids, or fatty acids in combination, such as fatty acid mixtures peculiar to the fatty acid components of the glycerides in natural oils. Fatty acid esters can be glycerides, such as monoglycerides, diglycerides and / or triglycerides; or alkyl esters of fatty acids, such as methyl esters or ethyl esters of fatty acids. Fatty acid esters can be derived from single fatty acids or fatty acid mixtures, such as fatty acid esters derived from natural fatty acid raw materials or natural oils. In certain embodiments, fatty acids or their alkyl ester derivatives are preferred over natural oils as fatty acyl sources.

[0049] Ester group quaternary ammonium salt can be prepared by C8-32 fatty acid or its alkyl ester derivative as saturated fatty acid, unsaturated fatty acid or saturated fatty acid and unsaturated fatty acid mixture.Preferably fatty acid is the fatty acid with the carbon chain length of 16 to 20 carbon atoms.Fatty acid can be derived from various sources, such as sunflower, mustard, corn, cottonseed, linseed, peanut, white meadowfoam, soybean, walnut, jojoba, palm, borage, safflower or rapeseed or its mixture.In certain embodiments, fatty acid is derived from mustard oil or low erucic acid rapeseed oil (LEAR).Preferably fatty acid comprises at least 50 weight % or at least 60 weight % unsaturated fatty acid group with at least one carbon-carbon double bond, and has iodine value in the range of 40 to 130, preferably 50 to 130, more preferably 60 to 130.

[0050] The iodine value represents the average iodine value of the parent fatty acyl compound or fatty acid of all ester quaternary ammonium salt materials present. In the context of the present technology, the iodine value is defined as the grams of iodine reacted with 100 grams of the parent compound. The method for calculating the iodine value of the parent fatty acyl compound / acid is known in the art and comprises dissolving a specified amount (0.1-3 g) into about 15 ml of chloroform. Subsequently, the dissolved parent fatty acyl compound / fatty acid is reacted with an acetic acid solution (0.1 M) containing 25 ml of iodine monochloride. To this, 20 ml of a 10% potassium iodide solution and about 150 ml of deionized water are added. After the halogen addition has occurred, the excess iodine monochloride is determined by titration with a sodium thiosulfate solution (0.1 M) in the presence of a blue starch indicator powder. At the same time, a blank is determined with the same amount of reagents and under the same conditions. 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 enables the calculation of the iodine value.

[0051] The amount of unsaturated fatty acid groups in the esterquat may affect the ability to obtain a concentrated liquid composition that remains stable. Esterquats made from fatty acid feedstocks having an average iodine value of less than about 40 may produce unstable concentrated liquid compositions.

[0052] The alkanolamines that can be used to prepare the ester quaternary ammonium salt active agents generally correspond to the following general formula:

[0053]

[0054] Wherein R1, R2 and R3 are independently selected from C1-C6 alkyl or hydroxyalkyl. Suitable alkanolamines include triethanolamine (TEA), methyldiethanolamine (MDEA), ethyldiethanolamine, dimethylamino-N-(2,3-propylene glycol), diethylamino-N-(2,3-propylene glycol), methylamino-N-2-ethanol-N-2,3-propylene glycol and ethylamino-N-2-ethanol-N-2,3-propylene glycol and mixtures thereof. The fatty acid: alkanolamine molar ratio is about 1.0:1 to about 2.2:1. In some embodiments, the alkanolamine is triethanolamine (TEA), and the fatty acid group: TEA molar ratio is about 1.3:1 to about 2.2:1 or about 1.3:1 to 1.8:1. In other embodiments, the alkanolamine is MDEA, and the fatty acid group: MDEA molar ratio is about 1.0:1 to about 2.0:1.

[0055] Preferably, the esterquat is a TEA-based esterquat having the following chemical structure:

[0056]

[0057] Each R is independently selected from C5-31 alkyl or alkenyl, or C7-21 alkyl or alkenyl, or C11-21 alkyl or alkenyl, or at least predominantly C13-17 alkyl or alkenyl, and may be straight chain or branched. Preferably, the compound of formula I contains different R groups derived from fatty acid materials having an average iodine value of 60 to 130. R1 represents C1-4 alkyl or hydroxyalkyl or C2-4 alkenyl,

[0058] T is

[0059] (i.e., forward or reverse ester bonds); n is an integer selected from 0 to 4 or 2 to 4; m is 1 for ester quaternary ammonium salts, 2 for diester quaternary ammonium salts, or 3 for triester quaternary ammonium salts, and represents the number of moieties directly suspended from the N atom to which it refers, and X is an ionic group, such as a halide or an alkyl sulfate, such as a C1-4 alkyl or hydroxyalkyl sulfate or a C2-4 alkenyl sulfate. Particularly contemplated anionic groups include chloride, methyl sulfate or ethyl sulfate.

[0060] The concentrated liquid composition comprises from about 30% to about 90% by weight, or from about 35% to about 85% by weight, or from about 40% to about 80% by weight, or from about 45% to about 75% by weight, or from about 45% to about 70% by weight, or from about 50% to about 60% by weight, or from about 55% to about 85% by weight of the esterquat active agent, based on the total weight of the composition.

[0061] Solvents

[0062] The concentrated liquid composition also comprises about 10% to about 50% by weight, or about 15% to about 45% by weight, or about 20% to about 40% by weight, or about 25% to about 35% by weight of a 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 a low VOC content, or does not contain VOC, and comprises a solvent mainly derived from a biorenewable source. Conventional solvents such as ethanol, propanol and butanol used in fabric softening compositions are undesirable for use in concentrated fabric softening compositions of the present technology because they are VOC solvents, derived from petroleum sources, or both. However, in some embodiments, the solvent system may include a VOC solvent, provided that the contribution of the VOC solvent to the concentrated fabric softening composition does not exceed 5% by weight, preferably does not exceed 2% by weight VOC, by the total weight of the composition. Preferably, only non-VOC solvents are used in the composition.

[0063] It is also desirable that the selected solvent has a BCI greater than 50, or greater than 60, or greater than 70, or greater than 80, or greater than 90. In some embodiments, solvents having a BCI less than 50 include solvents having a BCI of 0 (i.e., 100% petroleum based) that can be used in combination with solvents having a high BCI (greater than 50) to obtain a solvent system having a total BCI of at least 20, or between 20 and 60, or between 40 and 60, or at least 50, or at least 60.

[0064] Solvents that can be used in the solvent system include polyethylene glycol, fatty amides, 1,3-dialkoxy-2-propanol, glycol ethers, or combinations thereof. Polyethylene glycols that can be used are polyethylene glycols having a number average molecular weight in the range of 130 to 700, or 170 to 400, or 190 to 300, or 195 to 210. The number average molecular weight can be determined by methods known in the art, such as size exclusion chromatography. An example of a suitable polyethylene glycol (PEG) solvent is PEG200 (also known as PEG-4) having a number average molecular weight of about 200. PEG 200 is not a VOC solvent and can be obtained from Acme-Hardesty in a 100% plant-based form. When derived from a 100% plant-based source, PEG 200 has a BCI of 100.

[0065] Fatty amides that can be used in solvent systems have the following general structure:

[0066]

[0067] Wherein R is a branched or linear, saturated or unsaturated alkyl or alkenyl group having 6 to 20, preferably 8 to 14 carbon atoms, or a combination thereof. In some embodiments, R may contain one or more hydroxyl groups. 1 and R 2 R is independently hydrogen, C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and optionally branched when there are 3 or more carbon atoms, or a mixture thereof. Examples of raw materials that can be used to make the alkylamide include lauric fatty acids, myristyl fatty acids, coconut fatty acids, soybean fatty acids and ricinoleic fatty acids, or the corresponding methyl esters of these feeds. 1 and R 2 Specific examples of the group include methyl, ethyl and 2-propanol. Commercial examples of dialkylamides include, but are not limited to, those available under the trade name Diisopropylamide is available as a liquid from Colonial Chemical Company and is available under the trade name and Dimethylamide commercially available from Stepan Company. An example of a suitable alkylamide is CAA, a mixture of dimethyl lauramide and dimethyl myristic amide (CAA) available from Starpan Corporation. CAA is primarily derived from renewable sources, has a BCI of 86, and is a non-VOC solvent. Other examples of suitable alkyl amides available from Starpan Corporation are M-10 (N,N-dimethyldecylamide; M-10) and M-8-10 (a mixture of N,N-dimethyloctanamide and N,N-dimethyldecanamide; M-8-10); all carbons in these molecules except the methyl group on nitrogen are from plant sources. Another example is MET-10U (N,N-dimethyl 9-decenamide; MET-10U) - MET-10U is also available from Starpan Corporation.

[0068] The 1,3-dialkoxy-2-propanols that can be used in the solvent system have the following general structure:

[0069]

[0070] Where R a and R b Independently C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and optionally branched when there are 3 or more carbon atoms, or mixtures 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 and can be prepared by a synthetic route that utilizes biorenewable raw materials rather than petroleum-based raw materials. When derived from biorenewable raw materials, DEP has a BCI of 100.

[0071] The 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. An example of a suitable glycol ether is dipropylene glycol monomethyl ether (DPM). Although DPM has a BCI of 0, it can be combined with a solvent with a high BCI, such as CAA, so that the entire solvent system has a BCI of at least 20.

[0072] The solvent in the selected solvent system is such that the concentrated ester group quaternary ammonium salt composition is transparent, chemically stable, storage stable and water dispersible. In some embodiments, a transparent, stable, water dispersible concentrated composition having a solvent system comprising a single solvent can be obtained. In other embodiments, a mixture of specific solvents may be used to obtain the desired stability and water dispersibility. It has been found that the concentrated liquid composition comprising 1,3-dialkyl-2-propanol as the only solvent is stable and water dispersible. 1,3-dialkyl-2-propanol solvent can also be combined with one or more of the above-mentioned other solvents to form a solvent system. In some embodiments, a stable and water dispersible concentrated liquid composition can be obtained using a fatty amide (as defined above) in an amount of about 15% by weight to about 45% by weight of the composition as the only solvent. It has also been found that a solvent system comprising a mixture of at least one polyethylene glycol and at least one fatty amide as defined above can provide a transparent, stable and water dispersible concentrated liquid composition. The polyethylene glycol in the solvent system: fatty amide weight ratio can be in the range of 1:3 to 3:1 or 1:2 to 2:1. In one embodiment, the solvent system comprises a mixture of PEG 200 and CAA. A solvent system comprising a mixture of at least one glycol ether and at least one fatty amide as defined above can also provide a transparent, stable, water-dispersible concentrate composition. In some embodiments, the glycol ether: fatty amide weight ratio in the solvent system is about 2:1. In one embodiment, the solvent system comprises a mixture of DPM and CAA.

[0073] 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.

[0074] Liquid carrier

[0075] The concentrated liquid ester quaternary ammonium salt composition may contain 0 wt % to 30 wt % 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 compatibility. It should be understood that water should not be considered as part of the solvent system in any composition of the present invention. In some embodiments, the concentrated composition has a viscosity of less than 5,000 cP without the addition of water or other liquid carriers. In the embodiment, the composition may contain about 50 wt % to about 90 wt % ester quaternary ammonium salt and about 10 wt % to about 50 wt % solvent. Concentrated liquid compositions that do not include water have good stability during long-term storage because the absence of water will not cause the ester quaternary ammonium salt to hydrolyze.

[0076] Optional Ingredients

[0077] It is contemplated that the concentrated liquid composition may optionally contain additional ingredients as desired or required. Additional ingredients include, but are not limited to, nonionic surfactants, cationic surfactants, amphoteric surfactants, silicones such as polydimethylsiloxanes, aminosilicones or ethoxylated silicones, 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.

[0078] Auxiliary ingredients

[0079] Auxiliary ingredients may be added to the compositions of the present technology. The term "auxiliary ingredients" includes: dispersants, stabilizers, pH control agents, metal ion control agents, colorants, brighteners, dyes, deodorants, fragrance precursors, cyclodextrins, fragrances, solvents, soil release agents, preservatives, antimicrobial agents, dechlorinators, anti-shrinkage agents, fabric embrittlement agents, spot removers, antioxidants, anti-corrosion agents, thickeners, wrinkle and form control agents, smoothing agents, static control agents, wrinkle control agents, disinfectants, bactericides, bacteria control agents, mold control agents, mildew control agents , antiviral agents, desiccants, anti-pollution agents, malodor control agents, fabric renewal agents, chlorine bleach deodorants, dye fixatives, dye transfer inhibitors, color maintenance agents, color restoration, restoring agents, anti-fading agents, whiteness enhancers, anti-abrasion agents, anti-wear agents, fabric integrity agents, anti-wear agents, rinse aids, UV protectants, daylight darkening inhibitors, insect repellents, anti-allergic agents, enzymes, flame retardants, water repellents, fabric comfort agents, water conditioners, anti-shrinkage agents, anti-extension agents, and combinations thereof. Auxiliary components can be added to the concentrated liquid composition in an amount of 0% to about 3% by weight of the composition.

[0080] Composition properties

[0081] The concentrated liquid esterquat composition of the present technology is transparent, clear, and desirably has a transmittance percentage greater than about 50 at a wavelength of 420 nanometers when measured at 25°C in the absence of dyes and sunscreens. The composition has a measured viscosity of less than 5,000 cP at 25°C, or less than 3,000 cP at 25°C, or 1,000 cP at 25°C and a VOC content of less than 2% by weight by the total weight of the composition. In some embodiments, the solvent system has a BCI of at least 50. The solvent system can also allow the concentrated liquid composition to have a high load of fragrance or aromatic ingredients because the solvent system can incorporate hydrophobic ingredients into the composition. The high load of fragrance or aromatic ingredients will be between about 1% and 12% by weight, or between about 2% and 8% by weight, or between about 2% and 5% by weight.

[0082] Method for making concentrated softening composition

[0083] The concentrated liquid composition of the present technology can be prepared by simply mixing the ester group quaternary ammonium salt with the solvent system. If water is also included in the composition, it is desirable to mix the solvent system with water, and then add the ester group quaternary ammonium salt. Mixing can be carried out at ambient temperature, and there is no need to heat the components before mixing. However, heating the components may be desirable for easier mixing and for reducing the viscosity of the ester group quaternary ammonium salt for easier disposal. Optional ingredients and auxiliary ingredients can be added at any time.

[0084] Process for making dilute compositions from concentrates

[0085] It is contemplated that the concentrated liquid composition can be used as is without dilution. It is also contemplated that the concentrated liquid composition can be diluted with water before use, preferably to a concentration of about 2% to about 22% by weight, preferably about 3% to about 8% by weight of the esterquat active agent based on the total weight of the diluted composition. Since some embodiments of the concentrated liquid composition can be easily dispersed in water, it is contemplated that the dilution can be performed by the consumer. This use provides several advantages, such as reduced packaging requirements (due to the concentrated product) and reduced energy requirements for transportation and reduced transportation costs because less water is required for shipment.

[0086] It is also contemplated that a minimal amount of solvent system may be used to render the esterquat mobile for transport, such as an amount that provides a viscosity of about 5,000 cP or less at 25° C. The remainder of the solvent amount may then be added at the site where the fully concentrated liquid composition will be manufactured.

[0087] The concentrated liquid compositions of the technology of the present invention can also be shipped in concentrated form to consumer product manufacturers' places that cannot manufacture conventional liposome ester quaternary ammonium salt dispersions with equipment. Because some embodiments of the concentrated liquid compositions can be easily dispersed in water without high shear mixing or other special equipment, the consumer product manufacturers without the equipment can be easily produced at a dilution product between 2 wt % and 22 wt % activating agents. In certain embodiments, when the concentrated liquid compositions are diluted to an ester quaternary ammonium salt activating agent higher than the concentration of about 8 wt % of the dilution composition, it can be useful to include ionizable salts. Ionizable salts are generally used in more concentrated dispersions to reduce or control viscosity and / or stabilize dilution formulations.

[0088] A wide variety of ionizable salts can be used in the dilution dispersion. Examples of suitable salts are halides of metals of Group IA and IIA of the periodic table, such as calcium chloride, magnesium chloride, sodium chloride, potassium bromide, and lithium chloride. The amount of the ionizable salt used depends on the amount of the active ingredient used in the composition and can be adjusted according to the formulator's expectations. Typical levels of salts for controlling the viscosity of the composition are about 20 to about 20,000 parts per million (ppm), preferably about 20 to about 11,000 ppm, based on the weight of the diluted composition. Product manufacturers can also add optional or auxiliary ingredients to make the final diluted product.

[0089] Desirably, the concentrated liquid compositions of the present technology are stable concentrates and, if diluted prior to use, form stable liquid dispersions. A stable liquid concentrate or a stable liquid dispersion is defined as a liquid concentrate or liquid dispersion that does not phase separate or increase or decrease in viscosity by more than about 10% after storage for four weeks at 4°C and 40°C. Desirably, the concentrated liquid compositions and diluted liquid dispersions are also storage stable. As used herein, "storage stable" means that the composition does not phase separate or increase or decrease in viscosity by more than about 10% after storage for 52 weeks at temperatures that may be encountered on a retail shelf, such as at a temperature in the range of about 19°C to about 30°C.

[0090] Product Usage

[0091] The concentrated liquid composition of the present technology can be used, for example, as a concentrated liquid fabric softening composition in the rinse cycle of a domestic washing machine. The concentrated liquid fabric softening composition can be added directly in an undiluted state, such as through a dispenser drawer, or for a top-loading washing machine, directly into the drum. The amount of concentrated fabric softener added to the machine can be sufficient to deliver about 1.5g to about 8g of esterquat active agent per wash load. This amount generally provides about 0.04% to about 0.3% by weight of esterquat active agent to the fabric by weight of dry fabric. For example, in order to deliver 0.15% by weight of active agent esterquat (WOF) on dry fabric, for a 6 pound (2721.55g) load of dry cleaning, the dosage of 50% active agent esterquat formulation is 8.16g: (0.15% WOF) (2721.55g) / 50% = 8.16g, where WOF represents the weight on dry fabric. 0.15% WOF based on commercial quality fabric softener dosage for a medium sized load according to bottle instructions.

[0092] In certain embodiments, the concentrated fabric softening composition can be added to the washing machine in liquid form. In other embodiments, the composition can be dispensed as a fabric softening product such as, but not limited to, a box, a bag, a bag or a capsule. The fabric softening product has a water-soluble or water-breakable coating or film that encapsulates or contains a concentrated fabric softening composition of a unit dose. As used herein, the term "unit dose" refers to a fabric softening composition that should be delivered to a laundry solution to provide an effective amount of softening to a minimum amount of laundry products in a minimum volume of laundry solution. For laundry products with a larger load, multiple doses may be required to soften an effective amount. Water-soluble or water-breakable coatings or films are known in the art. Suitable materials for coatings or films include, but are not limited to, polyvinyl alcohol, polyvinyl pyrrolidone, methylcellulose, hydroxymethylcellulose, partially hydrolyzed vinyl acetate, gelatin and combinations thereof.

[0093] Alternatively, the concentrated liquid fabric softening composition can be diluted prior to use, preferably with water, to a concentration of about 2 wt % to about 22 wt %, preferably about 3 wt % to about 8 wt % of the esterquat active agent, based on the total weight of the diluted composition. Because some embodiments of the concentrated fabric softening composition can be easily dispersed, the dilution can be performed by consumers or consumer product manufacturers who do not have high shear mixing or specialized equipment typically used to make conventional liposomal fabric softener dispersions.

[0094] The fabric softening composition (concentrated or diluted) is added to the dispenser in an amount effective to soften and condition fabric articles under predetermined washing conditions. The fabric softening composition can also be used in a hand-washing laundry process, where the fabric softening composition is added to one or more rinse bath solutions to manually rinse fabric articles in a hand-washing laundry process. Alternatively, the composition can be used in a commercial automatic laundry operation.

[0095] The following examples will more fully illustrate embodiments of the present technology. Unless otherwise indicated, all parts, percentages and ratios mentioned herein and in the appended claims are by weight. Physical test methods are described below.

[0096] Examples

[0097] Example 1

[0098] The esterquat was made as follows - Canola fatty acid (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 sparging and distillation capabilities. The iodine number of this fatty acid was 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 fatty acid:TEA ratio in this mixture was 1.55:1. The reaction temperature was raised to 190°C and maintained for 3.5 hours. After 3.5 hours, the reactor was cooled and the esteramine intermediate was transferred for quaternization and testing (free amine = 1.77 meq / g, total acidity = 0.06 meq / g).

[0099] The esteramine intermediate (564g / mol, 3650.3g, 6.5mol) is added to a 5L reactor equipped with mechanical stirring, nitrogen headspace purge and reflux capacity. Stirring and nitrogen purge are started. The reaction temperature is adjusted to 50°C, and dimethyl sulfate (126g / mol, 774.8g, 6.1mol) is added dropwise over an hour. The temperature is controlled to a maximum of 85°C during the addition. The reactants are mixed at 85°C for 1 hour. 25% (wt) sodium chlorite (90.4g / mol, 9.8g, 0.03mol) is added and mixed for 30 minutes. The product is collected and tested (free amine = 0.08meq / g, cationic active agent = 1.17meq / g, total acidity = 0.10meq / g, Gardner Color = 4.6). A slightly yellow paste is obtained. This ester quaternary ammonium salt is represented as EQ1.

[0100] Example 2

[0101] Canola fatty acid (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, nitrogen subsurface sparging and distillation capabilities. The iodine number of this fatty acid was 111 and the fatty acid:TEA ratio was 2.00:1. Agitation was started and the contents were heated to 75°C. Nitrogen sparging was started. Subsequently, the reaction temperature was raised to 190°C and maintained for 4.5 hours. After 4.5 hours, the reactor was cooled and the esteramine intermediate was transferred for quaternization and testing (free amine = 1.48 meq / g, total acidity = 0.05 meq / g).

[0102] The esteramine intermediate (675g / mol, 753.7g, 1.1mol) is added to a 2L reactor equipped with mechanical stirring, nitrogen headspace purge and reflux capacity. Stirring and nitrogen purge are started. The reaction temperature is adjusted to 45°C. Dimethyl sulfate (126g / mol, 130.5g, 1.0mol) is added dropwise over one hour. The temperature is controlled to a maximum of 85°C during the addition. The reactants are mixed at 85°C for 1 hour. The product (free amine=0.09meq / g, cationic activator=1.16meq / g, total acidity=0.01meq / g) is collected and tested. A slightly yellow paste is obtained. This ester group quaternary ammonium salt is represented as EQ2.

[0103] Example 3

[0104] The animal fat fatty acid (272g / mol, 1067.05g, 3.9230mol) of distillation and the animal fat fatty acid (272g / mol, 409.89g, 1.5069mol) of hydrogenation are added to the reactor that 3L is equipped with mechanical stirring, nitrogen subsurface injection and distillation ability.The iodine value of this fatty acid mixture is about 34.Start stirring and content is heated to 75 ℃.Add triethanolamine (149g / mol, 521.3g, 3.4987mol), antioxidant 1010 (1178g / mol, 2.0g, 0.002mol) and phosphorous acid (82g / mol, 1.0g, 0.01mol).Fatty acid:TEA ratio is 1.55:1.Start nitrogen injection.Subsequently, reaction temperature is increased to 190 ℃ and kept for 4 hours. After 4 hours, the reactor was cooled and the esteramine intermediate was transferred for quaternization and testing (free amine = 1.81 meq / g, total acidity = 0.06 meq / g).

[0105] The esteramine intermediate (552g / mol, 1836.0g, 3.3mol) is added to a 3L reactor equipped with mechanical stirring, nitrogen headspace purge and reflux capacity. Stirring and nitrogen purge are started. The reaction temperature is adjusted to 45°C. Dimethyl sulfate (126g / mol, 381.8g, 3.0mol) is added dropwise over 30 minutes. The temperature is controlled to a maximum of 85°C during the addition. The reactants are mixed at 85°C for 1 hour. Dimethyl sulfate (126g / mol, 20.0g, 0.2mol) is added dropwise. The temperature is controlled to a maximum of 85°C during the addition. The reactants are mixed at 85°C for 1 hour. The product (free amine=0.08meq / g, cationic active agent=1.16meq / g, total acidity=0.17meq / g) is collected and tested. A waxy solid is obtained. This ester group quaternary ammonium salt is represented as EQ3.

[0106] Example 4

[0107] 1,3-diethoxy-2-propanol (DEP) with 100% BCI can be synthesized by at least two methods. For one method, sodium ethoxide can be reacted with 1,3-dichloro-2-propanol (dichloropropanol) using ethanol as a solvent, as reported by 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 a medium yield of the product. Scheme 1 below shows the described chemical process. A modified version of this method is used to synthesize the DEP used in the examples. Specifically, column chromatography is avoided by using filtration of the reaction mixture followed by distillation as the preferred separation and purification method.

[0108]

[0109] Scheme 1. Synthesis of DEP using 1,3-dichloropropanol as starting material.

[0110] A second method for producing DEP with 100% BCI involves reacting sodium ethoxide with epichlorohydrin as disclosed in Garcia, et al. Green Chem. 2010, 12, 426-434. DOI: 10.1039 / b92331g. In this case, epichlorohydrin is added to a solution of sodium ethoxide in ethanol in a controlled manner. The first step in the reaction is the attack of the sodium ethoxide on the epoxide ring, which opens the ring, and then the ring spontaneously closes on the opposite side to produce an ethoxy-substituted epoxide. Subsequently, a second mole of sodium ethoxide is reacted with the newly formed epoxide ring to produce a deprotonated diethoxy-2-propanol with a sodium counterion. Subsequently, the deprotonated diethoxy-2-propanol removes protons from the ethanol solvent to produce the desired product plus one mole of sodium ethoxide. Overall, two moles of sodium ethoxide react with epichlorohydrin to produce only one mole of sodium chloride. Once the reaction is considered complete, the reaction mixture is diluted with water, concentrated to remove volatiles, and then the product is isolated in good yield by column chromatography. Distillation can be used as a way to isolate the product and avoid column chromatography. The described chemical process is shown in Scheme 2.

[0111]

[0112] Scheme 2. Synthesis of DEP using epichlorohydrin as starting material.

[0113] Scheme 2 is preferred because it produces only 1 mole of sodium chloride, whereas Scheme 1 produces 2 moles of sodium chloride.

[0114] For a 100% BCI version of DEP, the raw materials used must be naturally derived. Ethanol is commercially available as a grain-based product, while both 1,3-dichloropropanol and epichlorohydrin can be obtained using the Dow Chemical Company's glycerol to epichlorohydrin (GTE) process, as described by Bell, et al., Clean 2008, 36(8), 657-661. DOI: 10.1002 / clen.200800067. The GTE process uses plant-based glycerol as a starting material, thus enabling the production of biorenewable 1,3-dichloropropanol and epichlorohydrin with 100% BCI content.

[0115] The formulations in the following examples were made by adding the solvent and water to a beaker followed by the addition of the esterquat. The mixture was then mixed for several minutes using an Ika benchtop mixer. The ingredients used when making formulations containing EQ1 were made at room temperature - none of the ingredients used to make the EQ1 formulations were heated prior to addition to the beaker and no heat was applied when mixing the batches. All formulations had a pH of 2.5 to 4.0. The pH was adjusted as needed to obtain formulations having a pH of 2.5 to 4.0.

[0116] The concentrated formulations indicated as transparent or clear formulations in the following examples are concentrated formulations having a percent light transmittance greater than about 50 at a wavelength of 420 nanometers using a 1 cm cuvette, wherein the composition is measured at 25°C in the absence of dyes and sunscreens. Alternatively, the clarity of the composition can be measured as having an absorbance (A) of less than about 0.3 at 420 nanometers, which in turn is equivalent to a percent transmittance greater than about 50 using the same cuvette as above. The relationship between absorbance and percent transmittance is: percent transmittance = 100 (1 / inverse log A). The formulation indicated as unstable means that the percent transmittance at 420 nm is less than 50% and / or the formulation is phase separated. "Phase separation" means that separate layers can be visually detected. Unless otherwise indicated, viscosity measurements were performed at room temperature (25°C) on a Brookfield DV-II+ viscometer using RVT spindle 4 at 50 RPM. The sample size in a 4 ounce jar was approximately 100 g.

[0117] Example 5

[0118] In this example, the formulations were prepared to evaluate the dispersibility of the formulations in water. Each formulation contained 50% by weight of EQ1 in the form of ester-based quaternary ammonium salts, 30% by weight of solvent, and 20% by weight of water. The difference in the formulations was the ratio of dimethyl lauramide / myristic amide (CAA) to polyethylene glycol 200 (PEG 200) in the solvent. The formulations are shown in Table 1. The dispersibility of each formulation in water was determined by the following test: 1 gram of the formulation was added to an 8-ounce wide-mouth bottle containing 120 ml of water, capped, and the mixture was shaken vigorously by hand 10 times. If there are no visibly precise particles after shaking, the formulation is considered to be easily dispersible. The results are shown in Table 1. Unless otherwise indicated below, all stable formulations are conveniently water dispersible. It is found that formulations that are stable but are considered to be not easily dispersible due to visible particles can still be used to manufacture dilute formulations in a manufacturing site that lacks equipment for making conventional liposome dispersions but still has mixing capabilities. Visible suspended particles of formulations that did not disperse easily eventually dispersed with more mixing than provided in the ready-to-use dispersibility test.

[0119] Table 1

[0120]

[0121] The results in Table 1 show that when CAA or PEG 200 is used as the only solvent, at an esterquat concentration of 50 wt%, the formulations are unstable. Similarly, when the CAA:PEG 200 ratio is 5:1 or 1:5, the formulations are unstable. However, the formulations with CAA:PEG 200 ratios ranging from 2:1 to 1:2 are all stable. The results show that the stability of the formulation can depend on the ratio of solvents in the solvent mixture. The results also show that solvent mixtures can provide formulation stability, while the same solvent used alone can produce unstable formulations.

[0122] Example 6

[0123] This example evaluates the softening ability of the formulations of the present technology compared to conventional ester quaternary ammonium salt dispersions. The formulation with 15% CAA and 15% PEG in Example 5 is used in this example. This formulation is dispersed in water to make a dispersion containing 5% by weight of ester quaternary ammonium salt active agent. A conventional liposome dispersion containing 5% by weight EQ1 is used as a comparator. Conventional liposome dispersions are prepared by slowly adding EQ1 to an appropriate amount of water under stirring over a period of about 3 minutes to 10 minutes, applying heat if necessary to improve mixing and promote liposome formation, and then continuing to mix for about 5 minutes to 15 minutes after all EQ1 has been added. Liposomes are formed during the mixing process to produce a 5% by weight EQ1 liposome dispersion. The softening test method used is based on ASTM D-5237. First, a white hand towel made of 86 / 14 cotton / polyester blend is subjected to a pre-wash process to remove any factory modifications. For each test, 160 towels are washed in a conventional household washing machine. Experimental fabric softener samples were given into the machine during the rinse cycle. The towels were then tumble dried and allowed to equilibrate to room temperature overnight. Next, panelists blindly evaluated pairs of towels through a paired comparison panel test. The number of votes for each sample was recorded. Using a unilateral direction difference test (Meilgaard, MC, Civille, GV, Carr, BT, Sensory Evaluation Techniques, 3rd edition, CRC Press, 1999, pp. 277-278, 355, 371), in a 160-vote observation test, a product needs to be selected at least 91 times at a 95% confidence level to be considered statistically superior to another product.

[0124] Using this test method, the 5% aqueous dispersion of the esterquat active of the formulation of Example 5 with 15% CAA and 15% PEG 200 was equivalent to the softening of the 5% EQ1 esterquat active conventional liposomal dispersion. The 5% dispersion of the formulation of Example 5 was easily made by gently mixing the formulation concentrate with water.

[0125] Example 7

[0126] Example 5 was repeated except that EQ2 was used as the esterquat in each formulation. EQ2 differed from EQ1 in that EQ2 had a fatty acid:TEA ratio of 2.00:1, while EQ1 had a ratio of 1.55:1. The formulations and results are shown in Table 2.

[0127] Table 2

[0128]

[0129] Table 2 shows that all formulations are unstable, indicating that the stability of the formulations may be affected by the fatty acid:TEA ratio used to make the esterquat. When using the PEG 200 / CAA solvent system and a canola fatty acid based esterquat (TEA / DMS), the results show that the fatty acid:TEA ratio should be below 2.0 to obtain a stable dispersion.

[0130] Example 8

[0131] Example 5 was repeated using only the stabilized formulation of Example 5 and replacing EQ3 as the esterquat in each formulation. EQ3 was made from a tallow fatty acid feedstock having an iodine value of 34 instead of the canola fatty acid feedstock used to make EQ1. The formulations and results are shown in Table 3.

[0132] Table 3

[0133]

[0134] Table 3 shows that the formulation is not stable, indicating that the stability of the formulation may also be affected by the iodine value of the fatty acid feedstock used to make the esterquat. When using the PEG 200 / CAA solvent system, the results show that the iodine value of the feed used to make the esterquat should be above 34 to obtain a stable dispersion.

[0135] Example 9

[0136] Using a range of different solvents, the Hansen polarity parameter for EQ1 was measured to be 10.9, while the Hansen polarity parameter for EQ3 was measured to be 4.4, according to the method described in the book Solubility Science, Principles and Practice, Steven Abbott, 2017, Creative Common NY-BD. Hansen solubility parameters are physicochemical parameters that can be used to predict the behavior of a given solvent or solute. These results show that the Hansen solubility parameters for EQ should be above about 5 when using the PEG 200 / CAA solvent system.

[0137] Example 10

[0138] In this example, formulations were prepared with different amounts of esterquat to evaluate the effect of esterquat concentration on formulation stability. The formulations and results are shown in Table 4.

[0139] Table 4

[0140]

[0141] As shown in Table 4, EQ1 with the PEG 200 / CAA solvent system is unstable at an esterquat concentration of 80 wt%. The results show that the upper limit of the esterquat in this composition should be below 80 wt% to obtain a stable composition. Although the 60% and 70% formulations in this example are stable, they are not readily water dispersible.

[0142] Example 11

[0143] 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. It was also completely removed from the fabric softener dispenser drawer in the front loader when running a regular cycle. The BCI for this solvent system consisting of DPM and CAA was calculated as follows:

[0144] The total carbon atom fraction is derived from DPM = (weight factor of 2) × (148.2 g / mol) × (6.022 × 10 23 molecules / mol)×(7 carbon atoms / molecule)=1.249×10 27 atoms of carbon, all of which come from non-biologically renewable sources.

[0145] The total carbon atom share comes from CAA = (weight factor of 1) × (234 g / mol) × (6.022 × 10 23 molecules / mol)×(14.5 carbon atoms / molecule)=2.043×10 27 carbon atoms, 86.2% of which come from biorenewable sources. This means that the amount of biorenewable carbon from CAA is 1.761×10 27 (2.043×10 27 multiplied by 0.862) and the number of non-biologically renewable carbon is 2.820×10 26 (2.043×10 27 Multiply by 0.138).

[0146] The total number of carbon atoms is 3.292×10 27 The BCI of the solvent system is:

[0147] BCI = 100 × [(1.761 × 10 27 ) / (3.292×10 27 )]=53.5.

[0148] Example 12

[0149] In this example, the effect of varying the amount of solvent in the solvent system was evaluated. The following formulations were prepared:

[0150] 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.

[0151] The solvent concentration was kept the same at 30%, but the amount of DPM and CAA solvents was changed. The formulations were found to be unstable even though the solvent components and total amount of solvents were the same as those used in Example 11. These results indicate that the relative amounts of solvents in the solvent system have an impact on the stability of the composition. The calculated BCI values ​​for the solvent system (DPM+CAA) for each of these formulations were 66.0 and 74.8, respectively.

[0152] Example 13

[0153] A formulation containing 80% EQ1 / 20% 1,3-diethoxy-2-propanol (DEP) was found to be clear, stable and dispersible in water. It was also completely removed from the fabric softener dispenser drawer in the front loader when running a regular cycle. The BCI of DEP is 100. This example shows that concentrated fabric softening compositions of the present technology can be prepared without water.

[0154] Example 14

[0155] A freeze / thaw stability comparison was performed between two formulations, each containing 5% EQ1. The first formulation was made by a traditional liposomal method, while the second formulation was made by diluting a liposomal formulation containing 50% EQ1, 15% bio-based PEG-200, 15% A second formulation was made from a concentrated formulation of CAA and 20% water. The freeze / thaw stability test method used was as follows:

[0156] 1. Prepare the sample and transfer it to a storage container (e.g., a 4-ounce jar)

[0157] 2. Place the sample in a -15°C freezer

[0158] 3. Allow the sample to stand at -15°C for 24 hours

[0159] 4. After 24 hours, remove the sample from the -15°C freezer and place it at room temperature.

[0160] 5. Allow the sample to thaw until it reaches room temperature (6 hours is usually sufficient time)

[0161] 6. Perform a visual inspection of the sample for phase separation, thickening / gelling, and inhomogeneity / caking

[0162] For three freeze / thaw cycles, the procedure was repeated three times.

[0163] The formulation made by the traditional liposomal route was thick and lumpy / non-uniform after one freeze / thaw cycle, while the 5% formulation made by diluting the 50% concentrate maintained the same viscosity and was uniform / non-lumpy after 3 freeze / thaw cycles. Conventional liposomes did not survive the freeze / thaw cycle because the liposomes "crack" during the freezing step. When they crack, they expose hydrophobic surfaces of the liposomes that do not want to be exposed to the aqueous phase. After thawing, those hydrophobic surfaces adhere to each other, but in a random inter-liposomal manner (i.e., not just recombining with their own lysed liposomes in an ordered manner within the liposome) to form large particles that produce visible thickening and clumping. Without being bound by theory, it is possible that non-liposomal structures are formed when the 5% dispersion is made by diluting the 50% concentrate - PEG-200 and The presence of CAA may be related to the formation of non-liposomal droplets. Alternatively, without wishing to be bound by theory, it is possible that if liposomes are present, then PEG-200 and / or The presence of CAA changes the properties of the liposomes so that they do not completely rupture after freezing.

[0164] Example 15

[0165] The ester bond hydrolysis of two formulations containing EQ1 at high storage temperature (50°C) was followed by NMR. The first formulation contained 50% EQ1, 15% bio-based PEG-200, 15% A concentrated formulation of CAA and 20% water. The second formulation was a 5% active agent EQ1 dispersion made by a conventional liposomal process. The percentages were normalized so that the total weight of TEA quat (no ester bond), monoester quat (one ester bond), diester quat (two ester bonds), and triester quat (three ester bonds) equaled 100%. After 9 weeks, the normalized weight percentage of TEA quat (without ester bonds and the final species formed during the hydrolysis process) in the concentrate was 8.2%, while for the conventional 5% formulation, the percentage was 20.2%. This indicates that the hydrolysis rate in the concentrate is cut by more than half, which results in a longer shelf life than conventional liposomal dispersions.

[0166] Example 16

[0167] A formulation was made using 70 wt% EQ1 and 30 wt% CAA. The formulation was stable and easily water dispersible. This result was unexpected considering that when 30 wt% CAA was used as the sole solvent in a formulation with a lower concentration of the same quaternary ammonium active agent (50% EQ1 / 30% CAA / 20% water formulation from Table 1 of Example 5), the formulation was unstable. It was unexpected that a formulation containing the same solvent at the same concentration, but with a higher concentration of quaternary ammonium active agent, could be stable when the lower quaternary ammonium concentration formulation was unstable.

[0168] Example 17

[0169] Formulations similar to those in Example 16 were made using M-10 or M-8-10 instead of CAA. These formulations were also stable and easily dispersed.

[0170] Example 18

[0171] Additional formulations found to be stable and easily dispersible are shown in Table 5.

[0172]

[0173] The results of Examples 16-18 demonstrate that stable highly concentrated (70-80 wt% active agent esterquat) compositions can be prepared using solvent systems containing fatty acid amides alone or in combination with polyethylene glycol.

[0174] The present invention is now described in such complete, clear and concise terms that it is possible for a person skilled in the art to practice the present invention. It should be understood that the foregoing describes preferred embodiments of the present invention and that modifications may be made therein without departing from the spirit or scope of the present invention as set forth in the appended claims. In addition, examples are provided that are not exhaustive but illustrate several embodiments that fall within the scope of the claims.

Claims

1. A transparent, stable liquid composition comprising: (A) 30% to 80% by weight, based on the weight of the composition, of one or more esterquats, wherein the one or more esterquats are the quaternization reaction product of a fatty acyl source having an iodine value of 40 to 130 reacted with triethanolamine at a fatty acyl:alkanolamine molar ratio of 1.3:1 to 1.8:1, or with methyldiethanolamine at a fatty acyl:alkanolamine molar ratio of 1.0:1 to 2.0:1, wherein the fatty acyl source is a C8-C32 fatty acid or a methyl or ethyl ester derivative thereof which is an unsaturated fatty acid, or a mixture of saturated and unsaturated fatty acids; (B) 20% to 50% by weight, based on the weight of the composition, of a solvent system, wherein the solvent system comprises a mixture of one or more polyethylene glycols having a number average molecular weight between 130 and 700 and one or more fatty amides having the following general structure: wherein R has 6 to 20 carbon atoms, is branched or linear, saturated or has one or more double bonds, optionally containing one or more hydroxyl groups; And R 1 and R 2 independently hydrogen, C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and when there are 3 or more carbon atoms, may be optionally branched; (C) optionally, 0 wt % to 30 wt % water; wherein the composition has a measured viscosity of less than 5000 cP at 25°C.

2. A transparent, stable liquid composition comprising: (A) 30% to 90% by weight, based on the weight of the composition, of one or more esterquats, wherein the one or more esterquats are the quaternization reaction product of a fatty acyl source having an iodine value of 40 to 130 reacted with triethanolamine at a fatty acyl:alkanolamine molar ratio of 1.3:1 to 1.8:1, or with methyldiethanolamine at a fatty acyl:alkanolamine molar ratio of 1.0:1 to 2.0:1, wherein the fatty acyl source is a C8-C32 fatty acid or a methyl or ethyl ester derivative thereof which is an unsaturated fatty acid, or a mixture of saturated and unsaturated fatty acids; (B) 10% to 50% by weight, based on the weight of the composition, of a solvent system comprising a mixture of (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 and (ii) one or more fatty amides having the general structure: wherein R has 6 to 20 carbon atoms, is branched or linear, saturated or has unsaturated double bonds, and optionally contains one or more hydroxyl groups; And R 1 and R 2 independently hydrogen, C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and when there are 3 or more carbon atoms, may be optionally branched; (C) optionally, 0 wt % to 30 wt % water; wherein the composition has a measured viscosity of less than 5000 cP at 25°C.

3. A transparent, stable liquid composition comprising: (A) 55% to 85% by weight, based on the weight of the composition, of one or more esterquats, wherein the one or more esterquats are the quaternization reaction product of a fatty acyl source having an iodine value of 40 to 130 reacted with triethanolamine at a fatty acyl:alkanolamine molar ratio of 1.3:1 to 1.8:1, or with methyldiethanolamine at a fatty acyl:alkanolamine molar ratio of 1.0:1 to 2.0:1, wherein the fatty acyl source is a C8-C32 fatty acid or a methyl or ethyl ester derivative thereof which is an unsaturated fatty acid, or a mixture of saturated and unsaturated fatty acids; (B) 15% to 45% by weight, based on the weight of the composition, of a solvent system comprising one or more fatty amides having the following general structure: wherein R has 6 to 20 carbon atoms, is branched or linear, saturated or has one or more double bonds, optionally containing one or more hydroxyl groups; And R 1 and R 2 is independently hydrogen, C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and when there are 3 or more carbon atoms, may be optionally branched; and (C) optionally, 0 wt % to 10 wt % water; wherein the composition has a measured viscosity of less than 5000 cP at 25°C.

4. The composition according to any one of claims 1 to 3, 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, preferably canola oil, LEAR rapeseed oil or a combination thereof.

5. The composition of any one of claims 1 to 3, wherein the fatty acyl source is canola fatty acid, LEAR rapeseed fatty acid, or a combination thereof.

6. The composition according to any one of claims 1 to 3, wherein the iodine value is 60 to 130.

7. The composition of any one of claims 1 to 3, wherein the esterquat has a Hansen polarity parameter greater than 5.

8. The composition of any one of claims 1 to 3, wherein the composition has a volatile organic compound content of less than 5% by weight.

9. The composition of any one of claims 1 to 3, wherein the viscosity is less than 3000 cP at 25°C.

10. The composition of claim 1, wherein the polyethylene glycol comprises polyethylene glycol 200.

11. The composition of any one of claims 1 to 3, wherein the fatty amide comprises dimethyl lauramide / dimethyl myristamide.

12. The composition of claim 10, wherein the fatty amide comprises dimethyl lauramide / dimethyl myristic amide, and polyethylene glycol 200 and dimethyl lauramide / dimethyl myristic amide are present in the mixture in a weight ratio of 1:3 to 3:

1.

13. The composition of claim 1 or 2, wherein the esterquat comprises 50 wt% and the solvent system comprises 30 wt% based on the weight of the composition.

14. The composition of claim 1, wherein the solvent system has a Total Biorenewable Carbon Index of at least 90.

15. The composition of claim 2, wherein the glycol ether comprises dipropylene glycol monomethyl ether.

16. The composition of claim 15, wherein the solvent system comprises dimethyl lauramide / dimethyl myristicamide, and the weight ratio of dipropylene glycol monomethyl ether to dimethyl lauramide / dimethyl myristicamide is 2:

1.

17. The composition of claim 2, wherein the solvent system has a total biorenewable carbon index between 20 and 60.

18. A composition according to any one of claims 1 to 3, wherein the composition is a fabric softening composition.

19. A fabric softening article comprising the fabric softening composition according to claim 18.

20. A fabric softener composition comprising water and the fabric softening composition of claim 18, wherein the one or more esterquats are present in the fabric softener composition in an active amount ranging from 2% to 22% by weight.

21. A fabric softener composition according to claim 20, wherein the one or more esterquats are present in the fabric softener composition in an active amount ranging from 3% to 8% by weight.

22. A fabric softener composition according to claim 20 or 21 further comprising at least one ionisable salt.

23. A method of making a fabric softener composition comprising the steps of: (A) providing a concentrated fabric softening composition, wherein the concentrated fabric softening composition comprises (i) from about 30% to about 80% by weight, based on the weight of the concentrated fabric softening composition, of one or more esterquat actives, wherein the one or more esterquat actives are the quaternization reaction product of a fatty acyl source having an iodine value of 40 to 130 reacted with triethanolamine at a fatty acyl:alkanolamine molar ratio of 1.3:1 to 1.8:1, or with methyldiethanolamine at a fatty acyl:alkanolamine molar ratio of 1.0:1 to 2.0:1, wherein the fatty acyl source is a C8-C32 fatty acid or a methyl or ethyl ester derivative thereof that is an unsaturated fatty acid, or a mixture of saturated and unsaturated fatty acids; (ii) 20% to 50% by weight, based on the weight of the concentrated fabric softening composition, of a solvent system, wherein the solvent system comprises a mixture of one or more polyethylene glycols having a number average molecular weight between 130 and 700 and one or more fatty amides having the following general structure: wherein R has 6 to 20 carbon atoms, is branched or linear, saturated or has unsaturated double bonds, and optionally contains one or more hydroxyl groups; And R 1 and R 2 independently hydrogen, C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and when there are 3 or more carbon atoms, may be optionally branched; and (iii) optionally, 0 wt % 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 % of an esterquat active agent based on the total weight of the dispersion, thereby forming the fabric softener composition.

24. A method of making a fabric softener composition comprising the steps of: (A) providing a concentrated fabric softening composition, wherein the concentrated fabric softening composition comprises (i) 30% to 90% by weight, based on the weight of the concentrated fabric softening composition, of one or more esterquat actives, wherein the one or more esterquat actives are the quaternization reaction product of a fatty acyl source having an iodine value of 40 to 130 reacted with triethanolamine at a fatty acyl source:alkanolamine molar ratio of 1.3:1 to 1.8:1, or with methyldiethanolamine at a fatty acyl source:alkanolamine molar ratio of 1.0:1 to 2.0:1, wherein the fatty acyl source is a C8-C32 fatty acid or a methyl or ethyl ester derivative thereof which is an unsaturated fatty acid, or a mixture of saturated and unsaturated fatty acids; (ii) from 10% to 50% by weight, based on the weight of the concentrated fabric softening 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 amides having the following general structure: wherein R has 6 to 20 carbon atoms, is branched or linear, saturated or has unsaturated double bonds, and optionally contains one or more hydroxyl groups; And R 1 and R 2 independently hydrogen, C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and when there are 3 or more carbon atoms, may be optionally branched; and (iii) optionally, 0 wt % 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 % of an esterquat active agent based on the total weight of the dispersion, thereby forming the fabric softener composition.

25. A method of making a fabric softener composition comprising the steps of: (A) providing a concentrated fabric softening composition, wherein the concentrated fabric softening composition comprises (i) from about 55% to about 85% by weight, based on the weight of the composition, of one or more esterquats, wherein the one or more esterquats are the quaternization reaction product of a fatty acyl source having an iodine value of 40 to 130 reacted with triethanolamine at a fatty acyl:alkanolamine molar ratio of 1.3:1 to 1.8:1, or with methyldiethanolamine at a fatty acyl:alkanolamine molar ratio of 1.0:1 to 2.0:1, wherein the fatty acyl source is a C8-C32 fatty acid or a methyl or ethyl ester derivative thereof that is an unsaturated fatty acid, or a mixture of saturated and unsaturated fatty acids; (ii) from 15% to 45% by weight, based on the weight of the composition, of a solvent system comprising one or more fatty amides having the following general structure: wherein R has 6 to 20 carbon atoms, is branched or linear, saturated or has one or more double bonds, optionally containing one or more hydroxyl groups; And R 1 and R 2 independently hydrogen, C1 to C6 alkyl or C2 to C6 alkenyl, optionally containing one or more hydroxyl groups and when there are 3 or more carbon atoms, may be optionally branched; (iii) optionally, 0 wt % to 10 wt % 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 wt % to 22 wt % of an esterquat active agent based on the total weight of the dispersion, thereby forming the fabric softener composition.

26. The method according to any one of claims 23 to 25, further comprising the step of adding an ionizable salt.

27. The method of claim 23, wherein the polyethylene glycol comprises polyethylene glycol 200.

28. The method of any one of claims 23 to 25, wherein the fatty amide comprises dimethyl lauramide / dimethyl myristamide.

29. A method according to any one of claims 23 to 25 wherein the concentrated fabric softening composition has a volatile organic compound content of less than 5% by weight.

30. The method of claim 23, wherein the solvent system has a Total Biorenewable Carbon Index of at least 90.

31. The method of any one of claims 23 to 25, wherein the viscosity is less than 3000 cP at 25°C.

32. The method of claim 24, wherein the glycol ether comprises dipropylene glycol monomethyl ether.

33. The method of claim 24, wherein the solvent system has a total biorenewable carbon index between 20 and 60.

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