SK125696A3 - Fabric softening composition - Google Patents

Abstract

A fabric softening composition comprising i) a substantially water insoluble fabric softening compound comprising a compound having two C12-22 alkyl or alkenyl groups connected to a quaternary ammonium head group via at least one ester link or a quaternary ammonium compound comprising of a single chain with an average chain length equal to or greater than C20 and a solubilising agent comprising an amphoteric surfactant and optionally a non-surfactant co surfactant; characterised in that when the fabric softening composition is diluted in water to a concentration of 5 wt.% of (i) and (ii), at least 70 wt.% of the fabric softening compound is in solution and the fabric softening compound has solubility less than 1 x 10exp(A3) % of demineralized water under 20 DEG.

Description

Technical field

The present invention relates to fabric softening compositions. In particular, the invention relates to fabric softening compositions having excellent stability, dispersing and dispersing properties.

BACKGROUND OF THE INVENTION

Fabric softening compositions added to the rinsing are well known. Typically, these compositions comprise a water-insoluble fabric softening agent dispersed in water having a softening agent content of up to 7% by weight, in which case the compositions are considered diluted, or at a level of 7% to 30% by weight, in which case the compositions are considered for concentrates. The fabrics may also be softened by using plastic coated sheets for use in tumble dryers. More specifically, commercially available fabric softeners form stacked lamellar structures having characteristic phase transition temperatures of 1> β to La.

The existing fabric softening compositions added to the rinse soften the deposition of the dispersed colloidal fabric softener particles onto the fabric, while the dryer sheets soften directly by transferring the molten softener, as outlined in RG Laughlin's Surfactant Science Courses 2, pages 449 to 465 (Marcel Decker, inc. 1991).

Conventional liquid fabric softening compositions are in the form of dispersed colloidal fabric softener particles. Fabric softening compositions comprising a dissolved fabric softening agent in an organic solvent and a powder or granular composition have also been described.

Fabric softening compositions of dispersed colloidal particles have complex, unstable structures. Because of this instability, it is with conventional softening compositions

- 2 fabrics connected many problems. Principal problems are: physical instability in storage at high and low temperatures; upon freezing, irreversibly converted to gels; it is difficult to obtain compositions which exhibit good dispersibility in the wash liquor, good deposition on fabric and good dispensability from the dispenser drawer of the washing machine. Poor dispersibility causes uneven coverage of the fabric softener on the laundry, and in some cases stains may occur. These problems are exacerbated in concentrated fabric softening compositions and after the addition of perfume.

Physical instability manifests as densification upon storage of the composition to a level when the composition is no longer liquid and may even lead to irreversible gel formation. Gel formation can also occur in the drawer of the machine when the temperature of the drawer rises due to warm water. Thickening is very undesirable since the mixture cannot then be conveniently used. Physical instability can also manifest itself as phase separation into two or more separate layers.

Consumers, however, desire good dispersibility and dispensability and stability at low or high temperature.

The problems associated with conventional dispersed colloidal particles are known in the art.

US 4 789 491 (Chang) discloses a specific process for preparing aqueous dispersions of cationic plasticizers. This process is said to overcome difficulties with product viscosity and poor dispersibility and dispersibility after storage.

EP 0 239 910 (Procter and Gamble) discloses compositions comprising dispersions of either a diester or a monoester of quaternary ammonium compounds in which nitrogen has either two or three methyl groups, stabilized by maintaining a critically low pH.

The physical stability of the fabric softening compositions added to the rinsing was improved by the addition of viscosity control agents or antigenic agents. In EP 13 780 (Procter and Gamble), for example, viscosity control agents are added to some concentrated mixtures. The reactants may contain C 1 -C 6 -cig fatty alcohols. Later in EP 280 550 (Unilever) it was proposed to improve the physical stability of dilute mixtures containing biodegradable quaternary ammonium and fatty acid by the addition of a nonionic surfactant. EP 507 478 (Unilever) discloses a physically stable fabric softening composition comprising water-insoluble, biodegradable ester-bound quaternary ammonium compounds and a non-ionic stabilizing agent.

Various proposals have already been made to supply fabric softeners in granular or powder form. EP 111074 is typical and uses silica gel as a plasticizer carrier. A drawback of using a carrier such as silica gel is that it enlarges the product and has no other function except that it makes the powder compatible with the other ingredients that the laundry powder may contain.

EP 569 184 (Unilever) describes the use of a granular mixture to form a pre-solution which is then added to the drawer of the washing machine container.

WO 92/18593 (Procter and Gamble) discloses a granular fabric softening composition that can be added to water to form an aqueous emulsion. The composition comprises a nonionic fabric softener such as a sorbitan ester and a single long alkyl chain cationic surfactant.

WO 93/23510 (Procter and Gamble) discloses liquid and solid fabric softeners comprising biodegradable quaternary ammonium fabric softening agents and a viscosity and / or dispersibility modifier. The application also describes a specific process for manufacturing these products. The viscosity and / or dispersibility modifier may be a single-chain alkyl cationic or nonionic surfactant. The solid mixture, when added to water, forms an emulsion or dispersion.

Our co-pending application GB 9323268.4 describes the use of tegobetain to overcome the problem of perfume-induced instability in a concentrated fabric softener.

In order to overcome the problems associated with dispersed colloidal particles, so far, fabric conditioners in the form of solutions of fabric softening agents in organic solvents have been focused. Mixtures of this type are exemplified by our co-pending application GB 9301811.7. However, dispersed colloidal particles are still formed upon contact with water.

Another way of making fabric conditioner solutions is through specific structural modifications.

US 3,892,669 (Lever Brothers) discloses a clear, homogeneous water-based liquid fabric softening composition and is limited to solubilized tetralkyl quaternary ammonium salts having two short chain alkyl groups and two long chain alkyl groups, the longer chain groups having several methyl and ethyl branches . Solubilizers include arylsulfonates, diols, ethers, low molecular weight quaternary agents, sulfobetaines, and nonionic surfactants. The application states that nonionic surfactants and phosphine oxides are unsuitable for use as such and are only useful as auxiliary solubilizers.

Surprisingly, we have found that, without the disadvantages of the prior art, a new fabric softening composition can be formed. The present invention describes fabric softening compositions having excellent softening properties and having excellent storage stability at both high and low temperatures, good freezing and thawing recovery, and excellent dispensability and dispersibility when the composition is concentrated and even, if the fabric softening agent is concentrated with levels above 30% by weight. In addition, the compositions prepared according to our invention do not suffer from a loss of softening efficiency.

SUMMARY OF THE INVENTION

Accordingly, in one aspect of the invention there is provided a fabric softening composition comprising

i) a substantially water insoluble fabric softening compound comprising two C ₁₂ _22 alkyl or alkenyl groups connected to the quaternary ammonium group via at least one ester link or a quaternary ammonium compound comprising a single chain of medium chain C2D or more; and ii) a solubilizing agent comprising an amphoteric surfactant and optionally a non-surfactant co-solubilizing agent;

characterized in that when the fabric softening composition is diluted in water to a concentration of 5% by weight (i) and (ii), at least 70% by weight of the fabric softening agent is in solution.

Another aspect of the invention provides the use of self-limiting molecular aggregates (as defined below) as a fabric softening composition.

DETAILED DESCRIPTION OF THE INVENTION

Without wishing to be bound by theory, it is believed that the fabric conditioner of the present invention is not in conventional lamellar form and when contacted with water can solubilize partially in the form of self-limiting molecular aggregates such as micelles or micellar solutions with solid or a liquid interior or mixtures thereof. When the composition is in a water-containing form, the composition itself may be at least partially in the form of molecular aggregates self-limiting in size. It is believed that this new structure of fabric softening compositions overcomes the problems of the prior art.

Suitably, the fabric softener and the solubilizing agent form a transparent mixture. The following assays can be used to ultimately determine whether or not a composition falls within the scope of this invention.

Test I

(a) The fabric softening composition is diluted with water to a concentration of 5% by weight (fabric softener and total solubilizing reagent, i.e. nonionic surfactant and some non-surfactant co-solubilizing reagent). The diluted solution is heated between 60-80 ° C, then cooled to room temperature and stirred for 1 hour to ensure equilibrium. A first aliquot of the resulting test liquid is removed and all water-insoluble material is separated by sedimentation or filtration until a clear aqueous layer is obtained. (Ultracentrifuges or ultrafilters can be used for this purpose.) Filtration can be performed by passing through subsequent filters of 1 gm, 0.45 gm and 0.2 gm.

b) The concentration of the fabric softener in the clear layer is measured by titration with a standard anionic surfactant (sodium dodecyl sulfate) using a dimidium sulfide disulfin blue indicator in two-phase titration with chloroform as the extraction solvent.

(c) The titration with the anionic surfactant is repeated with a second portion of the fabric softening composition that has been diluted but not separated.

d) Comparison b) with c) should show that the concentration of the fabric softener is at least 70% by weight (preferably 80% by weight) of the concentration of the fabric softener in c). This demonstrates that the fabric softener is in solution.

Test II

(a) The fabric softening mixture is diluted as for Test I.

(b) Measure the viscosity of the diluted mixture at a shear rate of 110 s' l.

c) The diluted solution is heated to 60 ° C and held at this temperature for 1 day.

(d) Cool the diluted solution to 20 ° C and measure the viscosity of the diluted mixture again at a shear rate of 110 s ¹ .

e) A comparison between viscosities b) and c) should show that they differ less by 5 mPas.

It is preferred that the fabric softening compositions of the present invention meet the following test:

Test III

(a) The fabric softening mixture is diluted as for Test I.

(b) Measure the viscosity of the diluted mixture at a shear rate of 110 s' Y

(c) The diluted solution is frozen and thawed.

d) Again, measure the viscosity of the diluate at a shear rate of 110 s ^- · '·.

e) The comparison between viscosities b) and c) should show that they differ less by 10 mPas.

The fabric softening compositions of the present invention may be translucent. Transparent in the context of the present invention is meant that if the fabric softening composition fills a cuvette to a height of 1 cm, a 12-point Courier font can be read through the cuvette.

A further advantage of the present invention is that the fabric softener composition is improved over prior art compositions with a similar level of fabric softener content.

The present invention has the advantage that a high level of perfume content can be tolerated without adversely affecting product stability.

Fabric softener

The fabric softening agent is suitably a water-insoluble quaternary ammonium material containing one alkyl or alkenyl having a chain length of ^C 20 or greater, or more preferably a fabric softening agent having a polar head group and two alkyl or alkenyl chains having an average length or greater, such as a quaternary ammonium material having two C 1-2-22 alkyl or alkenyl groups attached to the quaternary ammonium group by at least one ester bond.

Preferably, the fabric softener of the present invention has two alkyl or alkenyl chains with an average chain length or greater. More preferably, each chain has an average length or greater. Most preferably at least 50% of the alkyl or alkenyl groups have an average chain length of C 1-8 or greater.

It is preferred that the long-chain alkyl or alkenyl groups of the fabric softener are predominantly linear.

The fabric softening agents used in the compositions of this invention are molecules that provide excellent softening, characterized in that they have a Lp to La transition temperature greater than 25 ° C, preferably greater than 35 ° C, and most preferably greater than 45 ° C. This Lp to La transition can be measured by DSC as defined in Handbook of Lipid Bilayers, D. Marsh, CRC Press, Boca Raton Florida, 1990 (pages

137 and 337).

Substantially insoluble fabric softening agents in the context of the present invention are defined as fabric softening agents having a solubility in demineralized water at 20 ° C of less than 1 x 10% by weight. Preferably, the fabric softening agents have a solubility of less than 1 x 10% by weight. Most preferably, the fabric softening agents have a solubility at 20 ° C in demineralized water of from 1 x ΙΟ ^- ® to 10% by weight.

Preferred fabric softening agents are quaternary ammonium materials.

It is especially preferred if the fabric softening compound is a water insoluble quaternary ammonium material which comprises a compound having two ^ lkyl ^and 12-18 ° ^{in the} E or alkenyl groups connected to the molecule via at least one ester link. It is more preferred that the quaternary ammonium material has two ester bonds. A particularly preferred ester-linked quaternary ammonium material for use in the present invention may be represented by the formula:

R ¹

I

R ¹ - N ⁺ - (CH _{2) n} -TR ²

I (CH ₂ ) _n -TR ² wherein R 6 groups are independently selected from alkyl, hydroxyalkyl or C 2-4 alkenyl groups; and wherein the R groups are independently selected from Cg_ ₂ g alkyl or alkenyl groups;

0

U H

T is -O-C- or -C-O-; and n is an integer from 0 to 5.

Particularly preferred is di (tallow-oxyethyl) dimethylammonium chloride, available from Hoechst.

A second preferred type of quaternary ammonium material can be represented by the formula:

OOCR ²

I (R ¹ ) 3 N ⁺ - (CH 2) _{n -} CH

I ch ₂ oocr ²

Wherein R, n and R are as defined above.

It is advantageous from an environmental point of view if the quaternary ammonium material is biodegradable.

Preferred materials of this class, such as 1,2-bis [hardened tallow-yloxy] -3-trimethylammonium propyl chloride, and methods for their preparation, are described, for example, in US 4,137,180 (Lever Brothers). These materials preferably include small amounts of the corresponding monoester as described in US 4,137,180, for example, 1-stiffened tallow-2-hydroxy-3-trimethylammonium propyl chloride.

Amphoteric solubilizing reagent

The solubilizing agent is an amphoteric surfactant and is characterized in terms of its phase behavior. Suitable solubilizing agents are amphoteric surfactants for which in contact with water, the first lyotropic liquid crystalline phase formed is normally cubic (II) or normally cubic-bicontinuous (VI) or hexagonal (H1) or nematic (Nel) or intermedia (Intl). phase as defined in GJT Tiddy et al., J. Chem. Soc. Faraday Trans. 1, 79 975 (1983) and G. J. T. Tiddy, Modern Trends of Colloid Science in Chemistry and Biology, Ed. H.-F. Eicke, 1985 Birkhauser Verlag, Basel). La-phase surfactants at concentrations of less than 20% by weight are unsuitable.

In the context of the present invention, amphoteric surfactants are defined as having a molecular structure consisting of a hydrophilic and a hydrophobic moiety. The hydrophobic moiety contains a hydrocarbon and the hydrophilic moiety contains both a positive and a negative moiety. The amphoteric surfactants preferably comprise amino oxides, betaines, including sulfobetaines and tegobetaines, phosphine oxides and sulfoxides.

Mixtures of solubilizing reagents may be used.

For solid form compositions, especially powder, the solubilizing agent is desirably solid at room temperature, as this provides bulk particulate compositions.

It is particularly preferred that the solubilizing reagent further comprises a non-surfactant co-solubilizing reagent. Preferred co-solubilizing reagents include polyethylene glycol, urea, acid amides up to and including chain length C 8, citric acid and other polycarboxylic acids as described in EP 0 404 471 (Unilever), glycerol, sorbitol and sucrose. Particularly preferred are polyethylene glycols (PEG) having a molecular weight in the range of 200 to 6000, most preferably in the range of 1000 to 2000.

Preferably, the ratio of co-solubilizing reagent to amphoteric surfactant is from 2: 1 to 1:40. Preferably, the ratio of co-solubilizing reagent to nonionic surfactant is less than 1: 1, more preferably 1: 5.

It is preferred that the weight ratio of the solubilizing reagent (where relevant also includes a co-solvent) to the fabric softening agent is greater than 1: 6, preferably greater than 1: 4, more preferably 2: 3 or greater. It is preferred that the ratio of the solubilizing agent to the fabric softener is 4: 1 or less, more preferably below 3: 2.

It is preferred that the solubilizing agent / co-solubilizing agent is present with a heap higher than 5% by weight of the total composition, preferably at a level higher than 10% by weight.

The solubilizing reagent / co-solubilizing reagent may be present at a level greater than 20% by weight of the total composition, or even at a level greater than 30% by weight. Such high levels are particularly preferred when the fabric softening composition is solid.

pH of the mixture

The compositions of the invention preferably have a pH of greater than 1.5, preferably less than 5.

Other ingredients

The compositions may also contain fatty acids, for example, C 8 -C 24 alkyl or alkenyl monocarboxylic acids, or polymeric carboxylic acids. Preferably, saturated fatty acids are used, in particular C18 g fatty acid fatty acids.

The content of the fatty acid material is preferably greater than 0.1% by weight, more preferably greater than 0.2% by weight. Particularly preferred are concentrates containing from 0.5 to 20% by weight of fatty acid, more preferably 1% to 10% by weight. The weight ratio of the fabric softener to the fatty acid material is preferably from 10: 1 to 1:10.

The compositions of the invention may contain detergent ingredients and / or anionic surfactants as desired. However, it is particularly preferred that the composition is substantially free of detergent builders. It is also preferred that the composition is substantially free of anionic surfactant.

Suitably the mixture is substantially free of nonionic hydrophobic organic materials such as hydrocarbons and hydrocarbyl esters of fatty acids.

The compositions may also contain one or more optional ingredients selected from non-aqueous solvents, pH-maintaining agents, perfumes, perfume carriers, fluorescent agents, dyes, hydrotropes, antifoaming agents, antiredeposition agents, polymeric and other thickeners, enzymes, optical brighteners. anti-clotting agents, anti-creasing agents, anti-staining agents, germicides, fungicides, antioxidants, anticorrosive agents, antirusting agents, antistatic and ironing agents.

Product form

The product may be in any form. Particularly preferred forms are liquid or solid compositions and compositions suitable for coating onto a dryer sheet. The solid mixture in this context includes mixtures in the form of a tablet, gel, paste and preferably granules or powder.

The composition may be used in a tumble dryer, but is preferred for use in a washing machine, for example by dispensing the composition through a drawer of the washing machine, optionally with dilution prior to dispensing into the container drawer.

Preparation of the mixture

The invention further provides a method for preparing a rinse conditioner as described above, comprising the steps of:

i) mixing the substantially water-insoluble fabric softening agent and the solubilizing agent, preferably by co-melting;

ii) adding the resulting mixture to conventional ingredients such as water.

Alternatively, the compositions may be prepared by independently adding a water-insoluble fabric softening agent and a solubilizing agent to conventional ingredients.

Solid compositions can be prepared by spray drying, freeze-drying, grinding, extraction, cryogenic grinding or other suitable means.

DETAILED DESCRIPTION OF THE INVENTION

The invention will be further illustrated by the following non-limiting examples. All percentages in the examples are expressed as percent by weight.

The Comparative Examples are indicated by letters, while the Examples of the invention are indicated by numbers.

Preparation of Examples

The following examples were prepared by one of the following methods:

1) Co-melting the fabric softening agent in the solubilizing agent and adding the resulting dispersion in the desired amount of hot water.

2) Sequential addition of a fabric softener and a solubilizing agent in hot water.

In the comparative examples, where a solubilizing agent is not present, the cationic surfactant is dispersed in hot water (liquid mixtures).

In the Examples, the designation is:

HT TMAPC = 1,2-bis [hardened tallow-yloxy] -3-trimethylammonium propyl chloride

DEQA = di (solidified tallow-yloxyethyl) dimethyl ammonium chloride

Evaluation of softness

The softening performance was evaluated by adding 0.1 g of fabric softener (2 ml of 5% a.d. dispersion) to liquids to 1 liter tap water, 10 ° FH, at ambient temperature containing 0.001% by weight sodium alkylbenzenesulfonate (ABS) in a tergotometer. ABS was added to the simulated remainder of the main wash anionic detergent. Three pieces of terry cloth (8 cm x 8 cm, 40 g total weight) were added to the tergotometer vessel. The fabrics were treated for 5 minutes at 65 rpm, centrifuged to remove excess liquid and dried overnight.

Fabric softening was evaluated by an expert panel of 4 people using a circular paired comparison test protocol.

Each panel member evaluated four sets of test substances. Each test substance set contained one substance from each test system evaluated. Panelists were to assess softness on an 8-point scale. Softness scores were calculated using the Analysis of variance technique. Lower values indicate better softening.

Examples 1 to 3

The following examples were prepared by one of the standard methods.

Example - weight (g) component 1 2 3 HT TMAPC 1.2 1.2 0.9 CIO Sulfobetaine 0.3 - - C14 Sulfobetaine - 0.3 0.6 Water 8.5 8.5 8.5

The examples dispersed well and dispersed.

Examples 4 to 7 and A and B

Compositions having a range of ratio of fabric softener to solubilizing reagent were prepared by one of the methods described above in the Preparation Examples. Softening efficiency was determined.

Softening results

HT TMAPC: * L5351 (weight ratio) Softening score A 5: 0 2.5 4 4: 1 2.75 5 3: 2 3.0 6 2: 3 3.25 7 1: 4 5.5 B 0: 5 7.25

* fatty acid amidoalkylbetaine ex Th. Goldschmidt.

All blends 4 to 7 showed good softening efficiency and good stability. Mixture A settled in the freeze / thaw test as described above in Test III.

Examples 8 to 14 and C to F

The mixtures were prepared by one of the methods described above in the Preparation Examples. Softening efficiency was determined.

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d Λί U 3 r — I b x

Ό U • Η P X 0 0 x 2 cn I x C Ή at ε Ό D • H ι-i P P > s Ό 0 0 • H 1-1 at ε x Ό x 0 0 0 ε □ w 3 rh Ό • P > s R-1 3 P 0 Ό <u □ E ε D • H • rP •about X > s 1 H P 2 (D * x ε 2 ABOUT • H Ό II II Γ "ί > s P D at sP P m CZJ about n • P < Ω and Ό Ω Ω *

The storage stability of the blends 8-14 was determined by storing the blends under various conditions including freezing / melting mode and measuring viscosity with a Carri-med rheometer at a shear rate of 110 secl. The results are shown below.

Comparative mixtures were all settled or the components separated to illustrate poor stability.

8 9 10 11 12 13 14 initial viscosity 19.7 12.6 12.8 13.5 7.8 12.9 12.5 2 weeks F / T 25.4 24.8 12.3 12.5 18.9 13.2 12.9 4 ’C 27.2 25.3 12.5 12.8 12.5 14.0 12.9 22 ’C 28.7 30.4 15.1 13.4 16.5 14.0 13.6 37 ’C 15.1 10.2 46.9 29.5 54.9 14.1 13.9 4 weeks F / T 21.5 22.5 12.5 12.7 26.5 13.6 12.9 4 ’C 26.0 24.1 12.6 12.8 37.5 14.1 13.2 22 ’C 23.4 26.2 15.0 14.1 65.6 13.0 1'2,7 37 ’C 13.0 7.3 18.73 19.4 90.9 14.2 14.1 10 weeks F / T 16.3 15.1 12.6 12.7 46.2 13.5 12.8 4 ’C 16.1 27 12.4 12.3 15.1 14.2 13.2 22 ’C 24.9 18.7 16.0 14.1 41.7 15.1 12.9 37 ’C 71.8 61.6 21.5 16.1 531.2 16.1 14.5

All of the compositions of the present invention exhibited acceptable storage stability and did not settle in the freeze / melt mode.

The mixtures were analyzed in accordance with Test 1 described above and filtered by successive passage through filters with pore sizes of 1 μπι, 0.45 μπι and 0.2 μιη to achieve separation. The remaining cationic surfactant material was measured by standard titration.

Used non-ionic PAL % of the cationic PAL remaining after the 0.2 μιη filter 8 85 9 90 10 97.1 11 94.9 12 86.3 13 84.6 14 94.1 C 50 D 56 E 16 F too viscous for filter

PAL - surfactant

The mixtures were analyzed according to Test II and III described above. Viscosities were measured on a Carri-med at a shear rate of 110 CET ^- * · ·.

Product initial Viscosity / mPas test II test III 8 3.2 3.4 3.8 9 6.8 4.1 2.7 10 2.7 1.9 2.8 11 2.6 2.0 1.8 12 2.0 4.2 3.5 13 2.6 2.5 2.1 14 1.8 1.7 2.3 C 7.4 separated D separated separated E 57 95 F 111 separated

The softening effect of the mixtures was determined. The results are shown below using a 5% by weight solution of fabric softener and solubilizing reagent (3: 2 ratio).

Softening evaluation

sample Softening Stands. 5% HEQ 5: 0 3.0 10 2.75 13 3.75

Claims (10)

PATENT CLAIMS A fabric softening composition comprising i) a substantially water insoluble fabric softening compound comprising two ^ lkyl ^and 12-22 ° ^{in the} E or alkenyl groups connected to the quaternary ammonium group via at least one ester link or a quaternary ammonium compound comprising a single chain of medium chain C2Q or greater and; ii) a solubilizing agent comprising an amphoteric surfactant and optionally a non-surfactant co-solubilizing agent; characterized in that the weight ratio (ii) of the solubilizing agent to (i) of the fabric softener is greater than 1: 6 and when the fabric softener is diluted in water to a concentration of 5% by weight of (i) and (ii), at least 70 % by weight of the fabric softener is in solution. 2. A fabric softening composition according to claim 1, you characterized thereby, that the quaternary ammonium compound comprises a substantially water insoluble fabric softening compound comprising a compound having two C ^ ^{lkyl, and} 2-22 ° ^{in the} E or alkenyl attached to the quaternary ammonium group by at least one ester bond. The fabric softening composition of claim 1 or 2, wherein the solubilizing agent comprises an amphoteric surfactant and a non-surfactant co-solubilizing agent. The fabric softening composition of any preceding claim, wherein the ratio of the solubilizing agent to the fabric softening agent is in the range of 2: 3 to 4: 1. The fabric softening composition of any of the preceding claims, wherein the fabric softening agent has a solubility of less than 1 x 10% by weight in demineralized water at 22 ° C. The fabric softening composition according to any one of the preceding claims, characterized in that 1,2-bis [hardened tallow-yloxy] -3-trimethylammonium propyl chloride and 1-hardened tallow-yloxy-2-hydroxy-3-trimethylammonium propyl chloride. The fabric softening composition of any preceding claim, wherein the solubilizing agent content is greater than 10% by weight of the total composition. The fabric softening composition of any preceding claim, wherein the composition is in the form of molecular aggregates self-limiting in size. The fabric softening composition of any preceding claim, wherein the composition is in liquid form. The fabric softening composition of any one of claims 1 to 9, wherein the composition is granular or powdered.