QUATERNARY NITROGEN COMPOUND, FABRIC CARE COMPOSITION CONTAINING SAME, AND PROCESS FOR FORMING SAME

Abstract: A fabric care composition contains a fabric softening active and a carrier. The fabric softening active may contain a mixture of quaternary nitrogen compounds of general formula (II) where each R1 is independently selected from the group consisting of ethyl, propyl, isopropyl, or butyl; each R2 is independently selected from the group consisting of a saturated C1-22 alkyl group, or an unsaturated C1-22 alkyl group; each R3 is independently selected from the group consisting of a saturated C1-22 alkyl group, or an unsaturated C1-22 alkyl group; each n is independently from about 1 to about 25; m is from 0 to 4; o is from 0 to 4; m + o = 4; and X<-> is an anion. The mixture of quaternary nitrogen compounds contains at least about 5 % mono-ester quaternary nitrogen compound with m = 1 and o = 3, at least about 15 % di-ester quaternary nitrogen compound with m = 2 an o = 2, and at least about 5 % tri-ester quaternary nitrogen compound with m = 3 and o = 1. Also, a novel quaternary nitrogen compound has the above formula, where m = 4 and o = 0. Novel processes may be used to make these quaternary nitrogen compounds.

Description: QUATERNARY NITROGEN COMPOUND, FABRIC CARE COMPOSITION CONTAINING SAME, AND PROCESS FOR FORMING SAME FIELD OF THE INVENTION The present invention relates to a quaternary nitrogen compound, a fabric care composition containing a quaternary nitrogen compound, and a process for forming a quaternary nitrogen compound. BACKGROUND OF THE INVENTION Fabric softening actives are known additives for laundry applications which provide softer fabrics, reduce or eliminate static, reduce or eliminate wrinkles and enhance in-wear comfort. Traditionally, such fabric softening actives were used to provide benefits on fabrics such as clothes. These fabric softening actives are typically added in either the wash cycle as part of the detergent, or separately in the rinse and/or drying cycles of a laundering operation as, for example, liquid or solid fabric care compositions. During the wash, rinse, and/or drying cycles, these fabric softening actives transfer (e.g., from solution or a dryer sheet) onto clothes, to provide one or more of the above benefits. Typical fabric softening actives known in the art include amine-containing compounds, cationic fabric softening compounds such as quaternary nitrogen compounds, nonionic fabric softening compounds, and mixtures thereof. Processes for forming fabric softening actives are also known. As concern over the environment increases, it is becoming increasingly desirable to provide biodegradable fabric care compositions. While current fabric softening actives may be biodegradable, and may soften clothes and other fabrics, they tend to suffer from certain drawbacks. For example, they may not remain stable in an aqueous solution and/or in a fabric care composition; the typical fabric softening active is either biodegradable, or stable during storage, but rarely both. Thus, a biodegradable fabric softening active's stability over time may be limited, which in turn limits its commercial applicability. In addition to a loss of fabric softening activity, the degradation of a fabric softening active may create malodor problems, especially in hot, humid climates or storage conditions. Another disadvantage of many fabric softening actives is that they are often extremely viscous fluids, or solids which are accordingly difficult to formulate in an aqueous solution, especially for a clear, aqueous compositions. Thus, solvents and hydrotropes are often required in a clear fabric care composition. While these solvents and hydrotropes help solubilize the fabric softening active, they often are expensive, and/or do not otherwise improve the product's performance. It is thus desirable to improve fabric care composition stability, reduce formulation obstacles, improve softening performance, and improve anti-static performance, while simultaneously reducing formulation costs. Furthermore, it is desirable to increase both the stability and the biodegradability of a fabric softening active. Accordingly, there is a need for a fabric softening active which possesses improved stability, is easier to formulate, is biodegradable, and which has improved softening performance. There also exists a need for a process for making such a fabric softening active, and for a fabric care composition containing such a fabric softening active. SUMMARY OF THE INVENTION In one aspect, the present invention relates to a novel quaternary nitrogen compound of Formula I: (Formula I), where each R is independently selected from the group consisting of ethyl, propyl, isopropyl, and butyl; each R 2 is independently selected from the group consisting of a saturated C^ alkyl group, and an unsaturated C,.. 22 alkylgroup; each n is independently from about 1 to about 25; and X " is an anion. In another aspect, the present invention relates to a fabric care composition comprising a fabric softening active and a carrier. The fabric softening active comprises a mixture of quaternary nitrogen compounds of the general Formula II: (Formula II), where each R^ is independently selected from the group consisting of ethyl, propyl, isopropyl, and butyl; each R 2 is independently selected from the group consisting of a saturated C 22 alkyl group, and an unsaturated C^_ 22 alkyl group; each R 3 is independently selected form the group consisting of a saturated C . 22 alkyl group, and an unsaturated C _ 22 alkyl group; each n is independently from about 1 to about 25; m is from 0 to 4; o is from 0 to 4; m + o = 4; and X is an anion. The mixture of quaternary nitrogen compounds comprises at least about 5% mono-ester quaternary nitrogen compound with m = 1 and o = 3, at least about 15% di-ester quaternary nitrogen compound with m = 2 and o = 2, and at least about 5% tri-ester quaternary nitrogen compound with m = 3 and o = 1. In yet another aspect, the present invention relates to a process for forming a quaternary nitrogen compound comprising the steps of providing a starting material selected from the group consisting of ammonia, monoalkyl amine, dialkyl amines, and mixtures thereof, providing an alkoxylated reactant, providing a fatty acid reactant, and providing a quaternizing agent. The starting material is alkylated with the alkoxylated reactant to form a tertiary nitrogen compound, which is in turn reacted with the fatty acid reactant to form a tertiary alkoxylated ester having from 2 to 3 alkoxylated fatty acid moieties. This tertiary alkoxylated ester is then quaternized with the quaternizing agent to form a quaternary nitrogen compound. In another aspect, the present invention comprises a process for forming a quaternary nitrogen compound comprising the steps of providing a starting material selected from the group consisting of ammonia, monoalkyl amine, dialkyl amine, and mixtures thereof, providing an alkoxylated reactant, and providing a fatty acid reactant. The starting material is alkylated with the alkoxylated reactant to form a quaternized alkoxylated amine, which is in turn reacted with the fatty acid reactant to form a quaternary alkoxylated ester having from 3 to 4 alkoxylated fatty acid moieties. It has now been found that a novel quaternary nitrogen compound and mixtures of quaternary nitrogen compounds may serve as a fabric softening active. Furthermore, when included in a fabric care composition, this quaternary nitrogen compound may provide one or more benefits such as softer clothes, reduced static, easier formulation, increased biodegradability, lower formulation 105 costs, and improved storage stability. This improved stability is especially desirable in hot, humid climates and hot, humid storage conditions, which may promote hydrolysis and increase malodor issues. Moreover, it has been found that when the mono-, di-, and tri-ester forms of the quaternary nitrogen compounds described are combined, they provide 110 synergistic benefits, for example, improved softening benefits, easier formulation, and/or a significant reduction of hydrotropes. It has also now been found that when certain starting materials are employed, the quaternary nitrogen compounds described herein may be formed in an economical manner. These and other features, aspects, advantages, and variations of the 115 present invention, and the embodiments described herein, will become evident to those skilled in the art from a reading of the present disclosure with the appended claims, and are covered within the scope of these claims. DETAILED DESCRIPTION OF THE INVENTION 120 All percentages, ratios and proportions herein are by weight, unless otherwise specified. All temperatures are in degrees Celsius (°C) unless otherwise specified. All documents cited are incorporated herein by reference in their entireties. Citation of any reference is not an admission regarding any determination as to its availability as prior art to the claimed invention. 125 As used herein, the term "alkyl" means a hydrocarbyl moiety which is straight or branched, saturated or unsaturated. Unless otherwise specified, alkyl moieties are preferably saturated or unsaturated with double bonds, preferably with one or two double bonds. Included in the term "alkyl" is the alkyl portion of acyl groups. 130 As defined herein, the terms "mono-ester quaternary nitrogen compound" indicates a compound of Formula II where m = 1 and o = 3, while "di-ester quaternary nitrogen compound" indicates a compound of Formula II where m = 2 and o = 2, and "tri-ester quaternary nitrogen compound" indicates a compound of Formula II where m = 3 and o = 1. As used herein, the term "quaternary-ester 135 quaternary nitrogen compound" indicates a compound of Formula I, which correlates to a compound of Formula II, where m = 4 and o = 0. The present invention is directed towards a novel quaternary nitrogen compound, a fabric care composition containing a synergistic mixture of quaternary nitrogen compounds, and a process for forming a quaternary nitrogen 140 compound. The quaternary nitrogen compounds herein may be included in a fabric care composition, such as, a fabric softening composition, and/or a laundering composition. Preferred fabric care compositions include a liquid or solid rinse-added fabric softening composition, and a fabric softening composition for use in the drying-cycle. More preferably, the fabric care 145 composition is a rinse-added liquid fabric softening composition. The liquid fabric care compositions herein may be either clear, transparent, translucent, or opaque fabric care compositions. Quaternary Nitrogen Compound 150 The fabric softening active herein is a quaternary nitrogen compound, or a mixture of quaternary nitrogen compounds. This quaternary nitrogen compound may also be easier to formulate, and easy to prepare. Without intending to be limited by theory, it is believed that these compounds possess improved resistance to hydrolysis (e.g., alkaline-induced hydrolysis) during storage while 155 remaining readily biodegradable. It is believed that these quaternary nitrogen compounds are less subject to hydrolysis because they possess extended "oxyalkylene spacers" between the ester carbonyls and the quaternized nitrogen. These quaternary nitrogen compounds are especially resistant to hydrolysis if two or more such oxyalkylene spacers are present. This reduces the esters' 160 susceptibility to hydrolysis by increasing the spatial distance between the ester and nitrogen functional groups. Furthermore, the presence of alkoxy, and especially ethoxy groups, provide significant moisturization benefits for the fabric, improving the softening benefits. Without intending to be limited by theory, it is further believed that the alkoxy groups are susceptible to hydrolysis under acidic 165 conditions, and therefore are more easily biodegradable by, for example, bacteria. Accordingly, the novel quaternary nitrogen compounds of the present invention correspond to Formula I: (Formula I), 170 where each R is independently selected from the group consisting of ethyl, propyl, isopropyl, and butyl; preferably ethyl, and propyl; and more preferably ethyl. Each R 2 is independently selected from the group consisting of a saturated C 1-22 alkyl group, and an unsaturated C,. 22 alkyl group; and is preferably selected from the group consisting of a saturated C 12 . 18 alkyl group, and an unsaturated 175 C 12.18 alkyl group. Such R 2 groups may be straight chain, or branched, may be aliphatic, cyclic, or aromatic, and may or may not include other functional groups. Each n indicates the average degree of alkoxylation, and is independently from about 1 to about 25; preferably from about 1.1 to about 10; and more preferably from about 1.5 to about 5. In Formula I, X is an anion suitable for use in a fabric 180 care composition; preferably X is selected from the group consisting of a halide, and an alkyl sulfate; and more preferably X " is a halide. In addition to the novel quaternary nitrogen compound of Formula I, the present invention is also directed to a fabric care composition containing a fabric softening active comprising a mixture of quaternary nitrogen compounds of the 185 general Formula II: (Formula II), where each R.,, R 2 , n, and X are as defined above for Formula I. Each R 3 is independently selected from the group consisting of a saturated C _ 22 alkyl group, and an unsaturated Q, 22 alkyl group; and is preferably selected from the group 190 consisting of a saturated C 12 . 18 alkyl group, and an unsaturated C 12-18 alkyl group. Such R 3 groups may be straight chain, or branched, may be aliphatic, cyclic, or aromatic, and may or may not include other functional groups. Furthermore, m is from 0 to 4; o is from 0 to 4; and m + o = 4. When a mixture of quaternary nitrogen compounds of Formula II are 195 present in a fabric care composition, it has been found that significant benefits are found when the mono-, di-, and tri-ester quaternary nitrogen compounds are present at certain minimum levels. The mono-ester quaternary nitrogen compound of Formula II, where m = 1 and o = 3, is thus present at a level of at least about 5%, preferably about 20%, and more preferably about 30%, by 00 weight, of the mixture of quaternary nitrogen compounds of Formula II. It has also been found that it is desirable to maximize the proportion of di-ester quaternary nitrogen compound, to provide a balance between desirable fabric softening and solubility benefits. Therefore, the di-ester quaternary nitrogen compound of Formula II, where m = 2 and o = 2, comprises at least about 15%, 205 preferably at least about 30%, and more preferably at least about 40%, by weight, of the mixture of quaternary nitrogen compounds of Formula II. The tri- ester quaternary nitrogen compound of Formula II, where m = 3 and o = 1 , will typically be from about 5% to about 33%, preferably from about 7% to about 30%, and more preferably from about 10% to about 25%, by weight, of the 210 mixture of quaternary nitrogen compounds of Formula II. Thus, the mixture of quaternary nitrogen compounds comprises at least about 5% mono-ester quaternary nitrogen compound, at least about 15% di-ester quaternary nitrogen compound, and at least about 5% tri-ester quaternary nitrogen compound. Such fabric care compositions may further contain a quaternary-ester 215 quaternary nitrogen compound of Formula I. If present, then the quaternary- ester quaternary nitrogen compound of Formula I typically comprises from about 5% to about 33%, preferably from about 5% to about 30%, and more preferably from about 5% to about 25%, by weight, of the mixture of quaternary nitrogen compounds. 220 The compounds of Formula I and Formula II, and their weight percent in a composition or preparation, may be differentiated by 1 H NMR analysis and/or high performance liquid chromatography methods, as described below. If a clear, aqueous, isotropic liquid fabric care composition is desired, then it is highly preferred that the amount of di-ester quaternary nitrogen compound of 225 Formula II be at least equal, or greater than the total amount of the quaternary- ester quaternary nitrogen compound of Formula I plus the tri-ester quaternary nitrogen compound of Formula II. Without intending to be limited by theory, it is believed that while they provide better fabric softening benefits, the tri- and quaternary-ester quaternary nitrogen compounds are less soluble in aqueous 230 media than the mono- and di-ester quaternary nitrogen compounds. However, when present in the synergistic levels described above, it is believed that the mono- and di-ester quaternary nitrogen compounds, and especially the di-ester quaternary nitrogen compounds, serve as hydrotropes to help keep the tri-ester quaternary nitrogen compounds, and optionally the quaternary-ester quaternary 235 nitrogen compounds, in solution. Therefore, when present in these levels, a clear, aqueous, isotropic liquid fabric care composition may be produced. Such liquid fabric care compositions typically possess a viscosity of less than about 200 cps, preferably from about 50 cps to about 100 cps, as measured at 25 °C, by means of a glass capillary viscometer as set forth in Dow Corning Corporate 240 Test Method CTM0004, dated July 20, 1970. The fabric softening active comprising a mixture of quaternary nitrogen compounds of Formula II (and optionally Formula I) is typically present in the fabric care composition at a level of from about 0.1 % to about 60%, preferably from about 0.2% to about 35%, and more preferably from about 20% to about 245 35%, by weight of the fabric care composition. Carrier A liquid fabric softening composition typically requires a liquid carrier. The level of carrier is generally greater than about 50%, preferably greater than 250 about 65%, more preferably greater than about 70% of the fabric care composition. The carrier employed herein is preferably water due to its low cost, availability, safety, and environmental compatibility. The level of water in the liquid carrier is generally more than about 50%, preferably more than about 80%, and more preferably more than about 85%, by weight of the carrier. Mixtures of 255 water and organic solvents having low molecular weight, e.g., less than about 100 g/mol, are useful as the liquid carrier. Preferred organic solvents include low molecular weight alcohols such as ethanol, propanol, isopropanol or butanol; propylene carbonate; and/or glycol ethers. Useful low molecular weight alcohols also include dihydric alcohols (e.g., glycol), trihydric alcohols (e.g., glycerol), and 260 polyhydric (polyols) alcohols, such as C2-6 polyhydric alcohols. Principle Solvent The fabric care compositions may take the form of clear, transparent, or translucent liquid compositions. In such instances, the compositions may also 265 include a principle solvent. The principle solvent is one or more organic solvents which balance the level of fabric softening active and water, to produce a clear, transparent, or translucent liquid composition. Such a principle solvent possesses a ClogP value, as described below. The principle solvent is also selected to minimize solvent odor impact in the composition and to provide a low 270 viscosity to the final composition. It has been found that a principle solvent may further reduce turbidity, increase delivery of the fabric softening active to the fabric, increase stability, reduce viscosity for easy in-use dissolution, reduce formulation costs, and/or provide a desirable odor. The preferred principle solvent provides a highly concentrated fabric care 275 composition which has one or more of the benefits described above. The most preferred principle solvent may be identified by the appearance of softener vesicles, as observed via cryogenic electron microscopy of the compositions that have been diluted to the concentration used in the rinse. These dilute compositions appear to have dispersions of fabric softener that exhibit a more 280 uni-lamellar appearance than conventional fabric softener compositions. The closer to uni-lamellar the appearance, the better the compositions seem to perform. These compositions provide surprisingly good fabric softening and deposition as compared to similar compositions prepared in the conventional way with the same fabric softener active. Thus, the principle solvent in the principle 285 solvent system must be carefully selected. For example, isopropyl alcohol is not very effective at forming the desired softener vesicles, and has a strong odor, n- Propyl alcohol is more effective at forming the desired vesicles, but also has a distinct odor. Several butyl alcohols also have odors, but may be used for effective clarity/stability, especially when combined with another principle solvent 290 to minimize their odor. The preferred principle solvent is also selected for optimum low temperature stability, and is able to form a composition that is liquid, with an acceptable low viscosity and translucent, preferably clear, down to about 40 °F (about 4.4 °C), and is able to recover after storage down to about 5 °F (about -15 °C). 295 Accordingly, the suitability of any principle solvent for the formulation of the liquid, concentrated, preferably clear, fabric softener compositions herein with the requisite stability is surprisingly selective. A suitable principle solvent may be selected based upon its octanol/water partition coefficient (P). The octanol/water partition coefficient of a principle solvent is the ratio between its equilibrium 300 concentration in octanol and in water. The partition coefficients of the principle solvent of this invention is conveniently given in the form of their logarithm to the base 10, logP. The logP of many ingredients has been reported. For example, the Pomona92 database, available from Daylight Chemical Information Systems, Inc. 305 (Daylight CIS), Irvine, California, contains many, along with citations to the original literature. However, the logP values are most conveniently calculated by the "CLOGP" program, also available from Daylight CIS. This program also lists experimental logP values when they are available in the Pomona92 database. The "calculated logP" (ClogP) is determined by the fragment approach of Hansch 310 and Leo (cf., A. Leo, in Comprehensive Medicinal Chemistry, Vol. 4, C. Hansch, P. G. Sammens, J. B. Taylor and C. A. Ramsden, Eds., p. 295, Pergamon Press, 1990, incorporated herein by reference). The fragment approach is based on the chemical structure of each ingredient, and takes into account the numbers and types of atoms, the atom connectivity, and chemical bonding. These ClogP 315 values, which are the most reliable and widely used estimates for this physicochemical property, are preferably used instead of the experimental logP values in the selection of the principle solvent useful in the present invention. Other methods that may be used to compute ClogP include, e.g., Crippen's fragmentation method as disclosed in J. Chem. Inf. Comput. Sci., 27, 21 (1987); 320 Viswanadhan's fragmentation method as disclose in J. Chem. Inf. Comput. Sci., 29, 163 (1989); and Broto's method as disclosed in Eur. J. Med. Chem. - Chim. Theor., 19, 71 (1984). The principle solvent useful herein is selected from those solvents having a ClogP of from about 0.15 to about 0.64, preferably from about 0.25 to about 325 0.62, and more preferably from about 0.40 to about 0.60. The principle solvent is preferably at least somewhat asymmetric, and preferably has a melting, or solidification, point that allows it to be liquid at, or near room temperature. A principle solvent that has a low molecular weight and is biodegradable is also desirable. The more assymetric solvents appear to be very desirable, whereas 330 the highly symmetrical solvents such as 1 ,7-heptanediol, or 1 ,4- bis(hydroxymethyl) cyclohexane, which have a center of symmetry, appear to be unable to provide clear compositions when used alone, even though their ClogP values fall in the preferred range. Operable principle solvents are disclosed and listed below which have 335 ClogP values which fall within the requisite range. The principle solvent useful herein is selected from the group consisting of mono-ols, C 6 diols, C 7 diols, octanediol isomers, butanediol derivatives, trimethylpentanediol isomers, ethylmethylpentanediol isomers, propyl pentanediol isomers, dimethylhexanediol isomers, ethylhexanediol isomers, methylheptanediol isomers, octanediol 340 isomers, nonanediol isomers, alkyl glyceryl ethers, di(hydroxy alkyl) ethers, and aryl glyceryl ethers, aromatic glyceryl ethers, alicyclic diols and derivatives, C 3 -C 7 diol alkoxylated derivatives, aromatic diols, unsaturated diols, and mixtures thereof. A particularly preferred principle solvent is selected from the group consisting of hexanediols, such as 1 ,2-hexanediol and 2-ethyl-1 ,3-hexanediol, pentanediols, such as 2,2,4-trimethyl-1 ,3-pentanediol, and mixtures thereof. These principle solvents are disclosed in copending U.S. Patent Application numbers 08/621 ,019; 08/620,627; 08/620,767; 08/620,513; 08/621 ,285; 08/621 ,299; 08/621 ,298; 08/620,626; 08/620,625; 08/620,772; 08/621 ,281 ; 08/620,514; and 08/620,958, all filed March 22, 1996, and all having the title "CONCENTRATED, STABLE, PREFERABLY CLEAR, FABRIC SOFTENING COMPOSITION". When employed in the present invention, the principle solvent preferably comprises less than about 40%, preferably from about 2% to about 35%, more preferably from about 3% to about 25%, and even more preferably from about 4% to about 14%, by weight of the composition. Mono-Lonq-Chain-Alkyl Cationic Surfactant In a preferred embodiment, the fabric care composition further contains a mono-long-chain-alkyl (water-soluble) cationic surfactant, in addition to any quaternary nitrogen compounds of Formula II which are included in the tri-ester and/or quaternary-ester quaternary nitrogen compound synthesis process. Without intending to be limited by theory, it is believed that the mono-long-chain-alkyl cationic surfactant also acts as a hydrotrope for the tri- and quaternary-ester quaternary nitrogen compounds, and may further provide a fabric softening, or other benefits. For example, the mono-long-chain alkyl cationic surfactants may also be present as dispersability modifiers. If present, the mono-long-chain-alkyl cationic surfactants in liquid compositions are typically at a level of up to about 30%, preferably from about 0.5% to about 10% by weight of the final composition. To form a clear, or transparent liquid fabric care composition, the weight ratio of the mono-long-chain-alkyl cationic surfactant to the mixture of quaternary nitrogen compounds is from about 1 :1 to about 1 :8, preferably from about 1 :1 to about 1 :6. The mono-long-chain-alkyl cationic surfactants useful in the present invention are, preferably, quaternary ammonium salts of the general formula: (R 2 N + R 3 ) X- wherein the R 2 group is a C10-C22 hydrocarbon group, preferably C-12-C18 alkyl group or the corresponding ester linkage interrupted group with a short alkylene (C1-C4) group between the ester linkage and the N, and having a 380 similar hydrocarbon group, e.g., a fatty acid ester of choline, preferably C-12-C14 (coco) choline ester and/or C<\ Q- C18 tallow choline ester; each R is a C1-C4 alkyl or substituted (e.g., hydroxy) alkyl, or hydrogen, preferably methyl, and the counterion X" is a softener-compatible anion, for example, chloride, bromide, methyl sulfate, etc. 385 The ranges above represent the amount of the single-long-chain-alkyl cationic surfactant which is preferably added to the composition of the present invention. The long chain group R 2 , of the single-long-chain-alkyl cationic surfactant, typically contains an alkyl, or alkylene group having from about 10 to 390 about 22 carbon atoms, preferably from about 12 to about 16 carbon atoms for solid compositions, and preferably from about 12 to about 18 carbon atoms for liquid compositions. This R 2 group can be attached to the cationic nitrogen atom through a group containing one, or more, ester, amide, ether, amine, etc., preferably ester, linking groups which can be desirable for increased 395 hydrophilicity, biodegradability, etc. Such linking groups are preferably within about three carbon atoms of the nitrogen atom. Suitable biodegradable single-long-chain alkyl cationic surfactants containing an ester linkage in the long chain are described in U.S. Pat. No. 4,840,738 to Hardy and Walley, issued June 20, 1989. 400 It will be understood that the main function of the water-soluble cationic surfactant is to lower the composition's viscosity and/or increase the dispersability of the fabric softening active. Thus, it is not essential that the cationic surfactant itself have substantial softening properties, although this may be the case. Also, surfactants having only a single long alkyl chain, presumably 405 because they have greater solubility in water, may protect the fabric softener active from interacting with anionic surfactants and/or detergent builders. Other cationic materials with ring structures such as alkyl imidazoline, imidazolinium, pyridine, and pyridinium salts having a single C12- 30 alkyl chain can also be used. A very low pH is required to stabilize these ring structures 410 (e.g., imidazoline). Some alkyl imidazolinium salts useful in the present invention have the general formula: 415 wherein Y 2 is -C(0)-0-, -0-(0)-C-, -C(0)-N(R5), or -N(R5)-C(0)- in which R 5 is hydrogen or a C1-C4 alkyl radical; R6 is a C1-C4 alkyl radical; RJ and R^ are each independently selected from R and R 2 as defined herein before for the single-long-chain cationic surfactant with only one being R 2 . 420 Some alkyl pyridinium salts useful in the present invention have the general formula: wherein R 2 and X-are as defined above. A typical material of this type is cetyl pyridinium chloride. 425 Amine oxides can also be used. Suitable amine oxides include those with one alkyl, or hydroxyalkyl, moiety of about 8 to about 22 carbon atoms, preferably from about 10 to about 18 carbon atoms, more preferably from about 12 to about 14 carbon atoms, and two alkyl moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from one to about 430 three carbon atoms. Examples of amine oxides include: dimethyloctylamine oxide; diethyldecylamine oxide; dimethyldodecylamine oxide; dipropyltetradecylamine oxide; dimethyl-2-hydroxyoctadecylamine oxide; dimethylcoconutalkylamine oxide; and bis-(2-hydroxyethyl)dodecylamine oxide. 435 Additional Ingredients Fully formulated fabric softening compositions may contain, in addition to the herein before described components, one or more of the following ingredients. 440 Concentrated compositions of the present invention may require organic and/or inorganic concentration aids to go to even higher concentrations and/or to meet higher stability standards depending on the other ingredients. Surfactant concentration aids are typically selected from the group consisting of single long chain alkyl cationic surfactants; nonionic surfactants; amine oxides; fatty acids; or 445 mixtures thereof If present, such concentration aids are typically present at up to about 15% of the composition. In addition, the compositions of the present invention may include less than about 1 % by weight of an amphoteric surfactant. Preferably, the compositions include less than about 0.9% and more preferably less than about 450 0.75% by weight of an amphoteric surfactant. Viscosity/dispersability modifiers may be added for the purpose of facilitating the solubilization and/or dispersion, concentration, and/or improving phase stability (e.g., viscosity stability). Preferred dispersability modifiers may include nonionic surfactants. 455 Suitable nonionic surfactants to serve as the viscosity/dispersability modifier include addition products of ethylene oxide and, optionally, propylene oxide, with fatty alcohols, fatty acids, fatty amines, etc. They are referred to herein as, e.g., ethoxylated fatty alcohols, ethoxylated fatty acids, and ethoxylated fatty amines. 460 Any of the alkoxylated materials of the particular type described hereinafter can be used as the nonionic surfactant. In general terms, the nonionic surfactant herein, when used alone, is present at a level of up to about 5%, preferably from about 0.1% to about 5%, more preferably from about 0.2% to about 3%. Suitable compounds are substantially water-soluble surfactants of 465 the general formula: R 2 - Y - (C 2 H 4 0) z - C 2 H 4 OH wherein R 2 is selected from the group consisting of primary, secondary and branched chain alkyl and/or acyl hydrocarbyl groups; primary, secondary and branched chain alkenyl hydrocarbyl groups; and primary, secondary and 470 branched chain alkyl- and alkenyl-substituted phenolic hydrocarbyl groups; said hydrocarbyl groups having a hydrocarbyl chain length of from about 8 to about 20, preferably from about 10 to about 18 carbon atoms. More preferably the hydrocarbyl chain length is from about 16 to about 18 carbon atoms. In the general formula for the ethoxylated nonionic surfactants herein, Y is typically -0-, 475 -C(0)0-, -C(0)N(R)-, or -C(0)N(R)R-, preferably -0-, and in which R 2 , and R, when present, have the meanings given herein before, and/or R can be hydrogen, and z is at least about 8, preferably at least about 10-11. Performance and, usually, stability of the softener composition decrease when fewer ethoxylate groups are present. 480 The nonionic surfactants herein are characterized by an HLB (hydrophilic-lipophilic balance) of from about 7 to about 20, preferably from about 8 to about 15. Of course, by defining R 2 and the number of ethoxylate groups, the HLB of the surfactant is, in general, determined. However, it is to be noted that the nonionic ethoxylated surfactants useful herein, for concentrated liquid 485 compositions, contain relatively long chain R 2 groups and are relatively highly ethoxylated. While shorter alkyl chain surfactants having short ethoxylated groups may possess the requisite HLB, they are not as effective herein. Nonionic surfactants are preferred over other viscosity/dispersability modifiers disclosed herein for compositions with higher levels of perfume. 490 Examples of nonionic surfactants follow. The nonionic surfactants of this invention are not limited to these examples. In the following examples, the integer defines the number of ethoxy (EO) groups in the molecule. The deca-, undeca-, dodeca-, tetradeca-, and pentadecaethoxylates of n-hexadecanol, and n-octadecanol having an HLB within the range recited 495 herein are useful viscosity/dispersability modifiers in the context of this invention. Exemplary ethoxylated primary alcohols useful herein as the viscosity/dispersability modifiers of the compositions are n-C-j 8^0(10); and n-C-joEO(H). The ethoxylates of mixed natural or synthetic alcohols in the "tallow" chain length range are also useful herein. Specific examples of such 500 materials include tallow alcohol-EO(11 ), tallow alcohol-EO(18), and tallow alcohol -EO(25). The deca-, undeca-, dodeca-, tetradeca-, pentadeca-, octadeca-, and nonadeca-ethoxylates of 3-hexadecanol, 2-octadecanol, 4-eicosanol, and 5-eicosanol having and HLB within the range recited herein are useful 05 viscosity/dispersability modifiers in the context of this invention. Exemplary ethoxylated secondary alcohols useful herein as the viscosity/dispersability modifiers of the compositions are: 2-C-| 6^0(11 ); 2-C-2θEO(11 ); and 2 -C 16 EO(14). As in the case of the alcohol alkoxylates, the hexa- through 510 octadeca-ethoxylates of alkylated phenols, particularly monohydric alkylphenols, having an HLB within the range recited herein are useful as the viscosity/dispersability modifiers of the instant compositions. The hexa- through octadeca-ethoxylates of p-tridecylphenol, m-pentadecylphenol, and the like, are useful herein. Exemplary ethoxylated alkylphenols useful as the 515 viscosity/dispersability modifiers of the mixtures herein are: p-tridecylphenol EO(11 ) and p-pentadecylphenol EO(18). As used herein and as generally recognized in the art, a phenylene group in the nonionic formula is the equivalent of an alkylene group containing from 2 to 4 carbon atoms. For present purposes, nonionics containing a phenylene 520 group are considered to contain an equivalent number of carbon atoms calculated as the sum of the carbon atoms in the alkyl group plus about 3.3 carbon atoms for each phenylene group. The alkenyl alcohols, both primary and secondary, and alkenyl phenols corresponding to those disclosed immediately hereinabove may be ethoxylated 525 to an HLB within the range recited herein and used as the viscosity/dispersability modifiers of the instant compositions. Branched chain primary and secondary alcohols which are available from the well-known "OXO" process may be ethoxylated and employed as the viscosity/dispersability modifiers of compositions herein. 530 The above ethoxylated nonionic surfactants are useful in the present compositions alone or in combination, and the term "nonionic surfactant" encompasses mixed nonionic surface active agents. Mixtures of the above viscosity/dispersability modifiers are highly desirable. The single long chain cationic surfactant provides improved 535 dispersability and protection for the quaternary nitrogen compounds against anionic surfactants and/or detergent builders, such as those that may be carried over from the wash solution. If present, the viscosity/dispersability modifiers are present at a level of from about 0.1 % to about 30%, preferably from about 0.2% to about 20%, by weight of the fabric care composition. 540 Stabilizers may be present in the compositions of the present invention. The term "stabilizer," as used herein, includes antioxidants and reductive agents both of which are well-known in the art. These agents are typically present at a level of up to about 2%, preferably from about 0.01 % to about 0.2%, more preferably from about 0.035% to about 0.1% by weight of the composition for 545 antioxidants, and more preferably from about 0.01% to about 0.2% by weight of the composition for reductive agents. These assure good odor stability under long term storage conditions for the compositions and compounds stored in molten form. The use of antioxidants and reductive agent stabilizers is especially desirable for low scent products (low perfume). 550 Optionally, the compositions herein contain from 0.01% to about 10%, preferably from about 0.1 % to about 5%, more preferably from about 0.1 % to about 2%, of a soil release agent. Preferably, such a soil release agent is a polymer. Polymeric soil release agents useful in the present invention include copolymeric blocks of terephthalate and polyethylene oxide or polypropylene 555 oxide, and the like. U.S. Patent No. 4,956,447 to Gosselink, et al., issued September 11 , 1990, discloses specific preferred soil release agents comprising cationic functionalities. A preferred soil release agent is a copolymer having blocks of terephthalate and polyethylene oxide. More specifically, these polymers are 560 comprised of repeating units of ethylene and/or propylene terephthalate and polyethylene oxide terephthalate at a molar ratio of ethylene terephthalate units to polyethylene oxide terephthalate units of from about 25:75 to about 35:65, said polyethylene oxide terephthalate containing polyethylene oxide blocks having molecular weights of from about 300 to about 2,000 g/mol. The molecular weight 565 of this polymeric soil release agent is in the range of from about 5,000 to about 55,000 g/mol. U.S. Patent No. 4,976,879 to Maldonado, et al., issued December 11 , 1990, discloses specific preferred soil release agents which may also provide improved antistatic benefits, said patent being incorporated herein by reference. 570 Another preferred polymeric soil release agent is a crystallizable polyester with repeat units of ethylene terephthalate units containing from about 10% to about 15% by weight of ethylene terephthalate units together with from about 10% to about 50% by weight of polyoxyethylene terephthalate units, derived from a polyoxyethylene glycol of average molecular weight of from about 300 to about 575 6,000 g/mol, and the molar ratio of ethylene terephthalate units to polyoxyethylene terephthalate units in the crystallizable polymeric compound is between 2:1 and 6:1. Examples of this polymer include the commercially available materials Zelcon® 4780 (from DuPont) and Milease® T (from ICI). A more complete disclosure of these highly preferred soil release agents 580 is contained in European Patent Application 185,427 to Gosselink, published June 25, 1986. An optional cellulase may be used in the compositions herein. The cellulase can be any bacterial or fungal cellulase. Suitable cellulase is disclosed, for example, in GB-A-2 075 028, GB-A-2 095 275 and DE-OS-24 47 832. 585 Examples of such cellulase are cellulase produced by a strain of Humicola insolens (Humicola qrisea var. thermoidea). particularly by the Humicola strain DSM 1800, and cellulase 212-producing fungus belonging to the genus Aeromonas. and cellulase extracted from the hepatopancreas of a marine mollusk (Dolabella Auricula Sojander). 590 The cellulase added to the composition of the invention can be in the form of a non-dusting granulate, e.g. "marumes" or "prills", or in the form of a liquid, e.g., one in which the cellulase is provided as a cellulase concentrate suspended in a nonionic surfactant, or dissolved in an aqueous medium. Preferred cellulase for use herein are characterized in that they provide at 595 least 10% removal of immobilized radioactive labeled carboxymethyl-cellulose according to the C 14 CMC-method described in European Patent Application 350 098 A at 25x10"6 % by weight of cellulase protein in the laundry test solution. A highly preferred cellulase is that described in International Patent Application WO 91/17243. For example, a cellulase preparation useful in the 600 compositions of the invention can consist essentially of a homogeneous endoglucanase component, which is immunoreactive with an antibody raised against a highly purified 43kD cellulase derived from Humicola insolens. DSM 1800, or which is homologous to said 43kD endoglucanase. The cellulase herein should be used in the liquid fabric-conditioning 605 compositions of the present invention at a level equivalent to an activity from about 1 to about 125 CEVU/gram of composition (CEVU = Cellulase Equivalent Viscosity Unit, as described, for example, in WO 91/13136, and preferably an activity of from about 5 to about 100. Other preferred optional ingredients include, but are not limited to, dye 610 transfer inhibiting agents, polymeric dispersing agents, suds suppressors, optical brighteners or other brightening or whitening agents, dye fixing agents, light fading protection agents, oxygen bleach protection agents, traditional fabric softening agents (e.g., fabric softening clay, anti-static agents, anti-wrinkle agents, and/or other active ingredients), carriers, hydrotropes, processing aids, 615 dyes or pigments, bactericides, colorants, perfumes, preservatives, opacifiers, anti-shrinkage agents, fabric crisping agents, spotting agents, germicides, fungicides, anti-corrosion agents, and the like. Synthesis Process 620 The quaternary nitrogen compounds may be formed by first providing a starting material, an alkoxylated reactant, a fatty acid reactant, and a quaternizing agent. To form the mono-ester and di-ester quaternary nitrogen compounds, the starting material may be selected from various aliphatic and aromatic amines known in the art. However, to form the tri-ester and quaternary- 625 ester quaternary nitrogen compounds described by Formula II and Formula I, respectively, the starting material is selected from the group consisting of ammonia, monoalkyl amine, dialkyl amine, and mixtures thereof, preferably ammonia, monoalkyl amine, and mixtures thereof, and more preferably ammonia. Such starting materials are widely available, for example, from Kanto 630 Chemicals, Tokyo, Japan; Wako Chemicals, Osaka, Japan; and Sigma-Aldrich Chemicals, St. Louis, U.S.A. The alkoxylated reactant is typically a poly(oxyalkylene) material, corresponding to Formula III: X — (R ι O ) π — H '" (Formula III), 635 where R., and n correspond to R^ and n as described in Formula I and Formula II, and where X is a halide or alkyl sulfate, preferably a halide or methyl sulfate, and more preferably chlorine or bromine. Thus, the alkoxylated reactants are typically selected from the group consisting of halide and methyl sulfate derivatives of polyethylene oxides, polypropylene oxides, polyisopropylene 640 oxides, polybutylene oxides, and mixtures thereof; preferably polyethylene oxide halides, polyethylene oxide methyl sulfates, polypropylene oxide halides, polypropylene oxide methyl sulfates, and mixtures thereof; and more preferably polyethylene oxide chloride, polypropylene oxide chloride, and mixtures thereof. These alkoxylated reactants are available, for example, from Tokyo-Kasei 645 Chemicals, Tokyo, Japan; and Sigma-Aldrich Chemicals, St. Louis, U.S.A. The starting material is then alkylated with the alkoxylated reactant in a sealed vessel at about 90 °C for about 24 hours, after which time the vessel is cooled to room temperature and the reaction worked up. The key parameters of the alkylation reaction are dependent upon the degree of alkylation desired for 650 the particular starting material. To a single molar equivalent of amine are added sufficient alkoxylated reactant to achieve this alkylation and sufficient alkoxide base to neutralize the intermediate ammonium salt formed. The alkylation reaction takes place via a nucleophilic attack of the starting material's central nitrogen onto the carbon bearing the leaving group of the alkoxylated reactant. 655 The alkoxide base neutralizes the intermediate ammonium species to provide a free amine which can then undergo additional alkylation reaction to form a tertiary nitrogen compound. By adjusting the starting material, the ratio of starting material to alkoxylated reactant, and the ratio of starting material to alkoxide base, one can control the level of alkylation, so as to form a non, singly, 660 doubly, triply, or tertiary-alkylated tertiary nitrogen compound. Typically a mixture of these non, singly, doubly, and triply-etherified tertiary nitrogen compounds will be formed. In a preferred embodiment, the degree of alkylation is carefully controlled so as to provide the desired ratio of mono-ether, di-ether, tri-ether, and optionally 665 quaternary-ether quaternary nitrogen compound. This is especially desirable, as it allows much easier formulation and dispersal of the fabric softening active into a liquid. This is particularly desirable if the fabric care composition is to be a clear, liquid fabric care composition. The fatty acid reactant corresponds to the R 2 group of Formula I and/or 670 Formula II. Thus, the fatty acid reactant typically consists of an R 2 group, and a reactive moiety joined by a carbonyl group. The fatty acid reactant is typically of Formula IV: R 2 -< x (Formula IV), where R 2 corresponds to R 2 of Formula I and Formula II, and where X is the 675 reactive moiety. Thus, the R 2 group is selected form the group consisting of a saturated C^. 22 alkyl group, and an unsaturated C,.^ alkyl group; preferably a saturated C 12 . 18 alkyl group, and an unsaturated C 12-18 alkyl group. The reactive moiety is typically selected form the group consisting of a halide, and an -OH group; preferably chloride, bromide, and an -OH group; and more preferably 680 chloride, and an -OH group. Such fatty acid reactants are available, for example, from Kanto Chemicals, Tokyo, Japan; Wako Chemicals, Osaka, Japan; and Sigma-Aldrich Chemicals, St. Louis, U.S.A. The fatty acid reactant and the tertiary nitrogen compound are then 685 typically reacted in the presence of a solvent, to form a tertiary alkoxylated ester. This tertiary alkoxylated ester will typically contain a mixture of compounds having from zero to three, preferably two to three alkoxylated fatty acid moieties. When the fatty acid reactant is a fatty acid halide, then it is preferred that the solvent be an inert solvent, such as tetrahydrofuran. The fatty acid halide 690 reactant and the tertiary nitrogen compound are reacted in the presence of an organic acid scavenger in an inert solvent for about 3 hours at room temperature and then about 6 hours at elevated temperature to form a tertiary amine alkoxylated ester. The organic acid scavenger is typically a tertiary amine (pyridine, triethylamine, etc.) which accelerates the reaction and avoids 695 unwanted side reactions. Upon completion of the reaction and cooling to room temperature, this acid scavenger is typically converted to an ammonium salt which is easily removed from the reaction mixture. Following this, the reaction mixture may be worked up with ordinary procedures. This tertiary alkoxylated ester will typically contain a mixture of compounds having from zero to three, 700 preferably two to three alkoxylated ester moieties. When the fatty acid reactant is a fatty acid, it is preferable that the solvent also include a catalyst, preferably an alkaline earth metal hydroxide, in this reaction. The tertiary nitrogen compound, fatty acid, and alkaline earth metal hydroxide are then heated to form the tertiary alkoxylated ester. Without 705 intending to be limited by theory, it is believed that this helps increase yield, and achieve the final, desired levels of mono-, di-, tri-, and quaternary-ester quaternary nitrogen compounds. The quaternizing agent useful herein may be any of the quaternizing agents known in the art, such as alkyl halides, alkyl sulfates, or combinations 710 thereof, preferably alkyl halides and more preferably methyl chloride. However, if a quaternary-ester quaternary nitrogen compound is desired, then the quaternizing agent must be an appropriately substituted ester alkoxylate. These quaternizing agents are available from, for example, as chloromethane from Sigma-Aldrich Chemical or Acros Organics, iodomethane from Sigma-Aldrich 715 Chemical or Acros Organics, ethylbromide or benzyl bromide from Sigma-Aldrich Chemical or Acros Organics, and dimethyl sulfate from Sigma-Aldrich Chemical or Acros Organics. The tertiary alkoxylated ester is then reacted with the quaternizing agent in the presence of methanol, for about 24 hours, at about 35 °C, to form a 720 quaternary nitrogen compound as described herein. In another embodiment of the present invention, the quaternary nitrogen compounds may be formed by first providing a starting material, an alkoxylated reactant, and a fatty acid reactant, as described above. The starting material is alkylated with the alkoxylated reactant to form a quaternized alkoxylated amine, 725 and then reacted with the fatty acid reactant to form a quaternary nitrogen compound having from 3 to 4 alkoxylated fatty acid moieties, preferably a quaternary nitrogen compound of Formula I, having 4 alkoxylated fatty acid moieties. In this embodiment, the fatty acid reactant is preferably a fatty acid, as described above. 730 Typically, the quaternary nitrogen compound will contain a mixture of mono-ester quaternary nitrogen compounds, di-ester quaternary nitrogen compounds, tri-ester quaternary nitrogen compounds, and quaternary-ester quaternary nitrogen compounds. Preferably, the quaternary nitrogen compound contains a mixture of mono-ester quaternary nitrogen compounds to di-ester 735 quaternary nitrogen compounds to tri-ester quaternary nitrogen compounds, and optionally quaternary-ester quaternary nitrogen compounds, as is described above. This makes it easier to formulate these compounds in a fabric care composition, because it is less viscous, more easily dispersible, and more soluble in aqueous media than the pure tri-ester or quaternary-ester quaternary 740 nitrogen compounds themselves. The reactant products and/or the finished composition may be analyzed by, 1 H NMR and high performance liquid chromatography (HPLC) methods known in the art. The preferred technique for analyzing the presence of mono- ester, di-ester, tri-ester, or quaternary-ester quaternary nitrogen compounds is 745 by HPLC analysis of the mixture of quaternary nitrogen compounds. HPLC methods are especially useful, as they allow simultaneous analysis and fractionation of the mixture of quaternary nitrogen compounds. Using ordinary HPLC equipment and detection systems, the quaternary nitrogen compound species may be separated and quantitated with an ion-exchange 750 column (for example, Whatman PARTTISIL 10 SCX) and methanol containing ammonium formate as mobile phase. Under these conditions, the more highly alkoxylated ester quaternary nitrogen compounds will elute more quickly with the least alkoxylated ester quaternary nitrogen compound requiring the longest elution time. From this, the weight percentage of mono-ester, di-ester, tri-ester, 755 and quaternary-ester quaternary nitrogen compounds may easily be calculated. Examples of the invention are set forth hereinafter by way of illustration and are not intended to be in any way limiting of the invention. EXAMPLE 1 760 A 4.0 g portion of NaOH (100 mmole) is dissolved in 10 mL water and allowed to cool to room temperature in a thick walled glass cylinder fitted with a locking screw-type seal. To this is added a 36 mL portion (250 mmole) of 2-(2- (2-chloroethoxy)ethoxy)ethanol (EO=3, Tokyo Kasei Chemical, Tokyo, Japan) with stirring. A 3.4 mL portion of 28% aqueous ammonia (50 mmole, Wako 765 Chemicals, Osaka, Japan) is also added. The apparatus is sealed tightly, and then heated to 90 °C for 24 hours. This corresponds to a molar ratio of ammonia to polyethylene oxide chloride of about 1 :5 and forms a triply-alkylated tertiary nitrogen compound upon extraction and drying. The polyethylene oxide chloride is provided in excess to insure production of the triply-alkylated tertiary nitrogen 770 compound. A 5 gm portion of the tertiary nitrogen compound (12 mmole) is dissolved in 100 mL THF (tetrahydrofuran) containing 5.3 mL triethylamine (38 mmole). This is cooled to 0 °C and a 50 mL portion of THF containing 12.8 mL stearoyl chloride (38 mmole) is dripped in over a period of about 45 minutes. To assure 775 complete formation of the tertiary ethoxylated ester having three ester moieties, the fatty acid chloride is in a molar excess as compared to the alcohol moieties of the tertiary nitrogen compound. After stirring at room temperature for 2 hours, the mixture is heated to 60 °C and stirred for an additional 3 hours. After cooling to room temperature, the reaction mixture is further cooled to 0 °C and allowed to 780 stir overnight. The following day, the solid material is removed by suction filtration and the THF solvent of the liquid portion is removed in vacuo. The resulting syrupy material is dissolved in chloroform, extracted with 1 M NaOH, and dried with sodium sulfate. The solvent is then removed in vacuo. A 10 g portion of the tertiary ethoxylated ester (8.2 mmole) is dissolved in 785 150 mL ethanol with stirring. This is treated with 1 mL iodomethane (16.4 mL) and the solution is gradually warmed to 35 °C with stirring. After stirring for 24 hours, the solvent is removed in vacuo and the solid material recovered (the mixture of quaternary nitrogen compounds) is re-crystallized from hexane. HPLC analysis confirms presence of about 40% mono-ester quaternary nitrogen 790 compound, about 50% di-ester quaternary nitrogen compound, and about 10% tri-ester quaternary nitrogen compound. This is then fractionated with a high performance liquid chromatography column and stored. EXAMPLE 2 795 A 6.0 g portion of NaOH (15 mmole) is dissolved in 10 mL water and allowed to cool to room temperature in a thick walled glass cylinder fitted with a locking screw-type seal. To this is added a 36 mL portion (250 mmole) of 2-(2- (2-chloroethoxy)ethoxy)ethanol (EO=3, Tokyo Kasei Chemical, Tokyo, Japan) with stirring. A 3.4 mL portion of 28% aqueous ammonia (50 mmole, Wako 800 Chemical, Osaka, Japan) is also added. The apparatus is sealed tightly and heated to 90 °C for 24 hours. This corresponds to a molar ratio of ammonia to polyethylene oxide chloride of about 1 :5 and forms a quaternized ethoxylated amine with four ethylene oxide substituents. After extraction to remove excess polyethyleneoxide derivative, the aqueous layer is dried to remove water and the 805 quaternized ethoxylated amine is poured away from the sodium chloride. The polyethylene oxide chloride is provided in excess to insure production of the quaternized ethoxylated amine. A 10 gm portion of the quaternized ethoxylated amine (17 mmole) is heated with 19.5 g stearic acid (68 mmole) to 220 °C in the presence of 0.2 g tin 810 powder. This is stirred mechanically for at least 2 hours until the removal of water is complete. The mixture is then cooled to approximately 60 °C and the viscous oil is poured away from the tin powder and allowed to cool into a solid mass. The mixture contains about 30% mono-ester quaternary nitrogen compound, about 45% di-ester quaternary nitrogen compound, about 15% tri- 815 ester quaternary nitrogen compound, and about 10% quaternary-ester quaternary nitrogen compound. This is then fractionated with a high performance liquid chromatography column and stored. EXAMPLE 3 820 Liquid fabric softening compositions are prepared as follows: The fabric softening active is melted in a water bath at a temperature of from about 70 °C to about 75 °C to from a molten organic phase. The mono- long-chain-alkyl cationic surfactant is premixed with 1 ,2 hexane diol and then added to the molten organic phase. Separately, the silicone anti-foaming agent 825 and hydrochloric acid are added to water, covered and heated to a temperature of from about 70 °C to about 75 °C. The aqueous system is transferred to an insulated baffled mixing vessel which is fitted with a turbine blade impeller at a temperature of from about 70 °C to about 75 °C. The molten organic phase is slowly added to the aqueous phase 830 under high speed agitation. The dispersion becomes highly viscous. A small portion of the total calcium chloride is slowly added to the dispersion as a 2.5% solution. The dispersion is milled using a probe rotor-stator high shear device for a period of time corresponding to batch size. The milled product is chilled in an ice 835 bath to room temperature over a 3-6 minute period. The other ingredients, minors, and remaining calcium chloride are added with vigorous mixing. Dye is then added as desired. The final product is very fluid with a viscosity of less than 100 cps. These liquid fabric softening compositions are formulated as follows: 840 A B C D E (1) quaternary nitrogen compound mixture of Example 1 (2) quaternary nitrogen compound mixture of Example 2 (3) C 12 -C 14 dimethyl hydroxyethyl quaternary ammonium chloride The above formulation examples provide excellent softening benefits, and are surprisingly stable, while remaining readily biodegradable. Examples B-E, are clear, transparent, aqueous, isotropic liquids.

Claims: WHAT IS CLAIMED IS: 1. A quaternary nitrogen compound of Formula I: X- (Formula I), where each R is independently selected from the group consisting of ethyl, propyl, isopropyl, and butyl; each R 2 is independently selected from the group consisting of a saturated C 1-22 alkyl group and an unsaturated C,. 22 alkyl group; each n is independently from about 1 to about 25; and X is an anion. 2. A fabric care composition comprising the quaternary nitrogen compound of Claim 1. 3. The fabric care composition of Claim 2, further comprising a principle solvent. 4. A fabric care composition comprising: A. a fabric softening active comprising a mixture of quaternary nitrogen compounds of the general Formula II: (Formula II), where each R 1 is independently selected from the group consisting of ethyl, propyl, isopropyl, and butyl; each R 2 is independently selected from the group consisting of a saturated C 1-22 alkyl group, and an unsaturated C _ 22 alkyl group; each R 3 is independently selected form the group consisting of a saturated C,_. 22 alkyl group, and an unsaturated C _ 22 alkyl group; each n is independently from about 1 to about 25; m is from 0 to 4; o is from 0 to 4; m + o = 4; and X " is an anion, wherein the mixture of quaternary nitrogen compounds comprises at least about 5% mono-ester quaternary nitrogen compound with m = 1 and o = 3, at least about 15% di-ester quaternary nitrogen compound with m = 2 and o = 2, and at least about 5% tri-ester quaternary nitrogen compound with m = 3 and o = 1 ; and B. a carrier. The fabric care composition of Claim 4, wherein the mixture of quaternary nitrogen compounds further comprises from about 5% to about 33% of a quaternary-ester quaternary nitrogen compound of Formula I: (Formula I), where each R 1 is independently selected from the group consisting of ethyl, propyl, isopropyl, and butyl; each R 2 is independently selected from the group consisting of a saturated , 22 alkyl group and an unsaturated C^_ 22 alkyl group; each n is independently from about 1 to about 25; and X is an anion. 6. A fabric care composition of Claim 4, further comprising a principle solvent. 7. The fabric care composition of Claim 4, further comprising a mono-long-chain-alkyl cationic surfactant. 8. The fabric care composition of Claim 6, wherein the fabric care composition is a clear, liquid fabric care composition. 9. The fabric care composition of Claim 7, wherein the weight ratio of mono-long-chain-alkyl cationic surfactant to the mixture of quaternary nitrogen compounds is from about 1 :1 to about 1 :8. 10. A process for forming a quaternary nitrogen compound comprising the steps of: A. providing a starting material selected from the group consisting of ammonia, monoalkyl amine, dialkyl amine, and mixtures thereof; B. providing an alkoxylated reactant; C. providing a fatty acid reactant; D. providing a quaternizing agent; E. alkylating the starting material with the alkoxylated reactant to form a tertiary nitrogen compound; F. reacting the fatty acid reactant and the tertiary nitrogen compound to form a tertiary alkoxylated ester having from 2 to 3 alkoxylated fatty acid moieties; G. quaternizing the tertiary alkoxylated ester with the quaternizing agent to form a quaternary nitrogen compound. 11. The quaternary nitrogen compound formed by the process of Claim 10, wherein the quaternary nitrogen compound contains 3 or 4 alkoxylated fatty acid moieties. 12. A process for forming a quaternary nitrogen compound comprising the steps of: A. providing a starting material selected from the group consisting of ammonia, monoalkyl amine, dialkyl amine, and mixtures thereof; B. providing an alkoxylated reactant; C. providing a fatty acid reactant; D. alkylating the starting material with the alkoxylated reactant to form a quaternized alkoxylated amine; and E. reacting the fatty acid reactant and the quaternized alkoxylated amine to form a quaternary nitrogen compound having from 3 to 4 alkoxylated fatty acid moieties.

Inventors: BRYANT LONNIE LIDDELL JR, MAO HSIANG-KUEN, TEE JOHANNSON JIMMY, BRYANT, LONNIE, LIDDELL, JR., MAO, HSIANG-KUEN, TEE, JOHANNSON, JIMMY
Applicants: BRYANT LONNIE LIDDELL JR, MAO HSIANG KUEN, PROCTER & GAMBLE, TEE JOHANNSON JIMMY, BRYANT, LONNIE, LIDDELL, JR., MAO, HSIANG-KUEN, TEE, JOHANNSON, JIMMY, THE PROCTER & GAMBLE COMPANY
Application year: 1999
Main classification: C07C217
IPC codes: C07C217, C11D1, C11D3