GB1597357A - Fabric softening agent - Google Patents

Description

(54) IMPROVED FABRIC SOFTENING AGENT (71) We, PETER JOWETT, PETER JOHN ROBBINS, PETER NAYLER, British Subjects of Tame Street, Stalybridge, SK15 1QW, Cheshire, do hereby declare the invention for which we pray that a Patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: This invention relates to fabric softening or fibre conditioning composition.

Fabric softening or fibre condition agents are well established for use in domestic and industrial laundering of clothes, in the textile industry as finishing agents and in the dry-cleaning industry as softening agents. The same chemical types have becomes established, also, in the hair-care industry as conditioning agents for the hair.

The textile softening agents which are available include those of the anionic, cationic and non-ionic types. Of these, the cationic types are those which are generally used in the laundering, dry cleaning and hair care industries on account of their substantivity to both natural and synthetic fibres.

The most important groups of cationic chemicals which have the ability to condition fibres are those which contain a quaternary ammonium grouping within the molecule.

It is widely recognized that the fabric softening and fibre conditioning properties of this type of chemical are directly related to the length of the alkyl chains present in the molecule. Furthermore it is recognized also, that chemicals of this type which contain two long chain alkyl groups are more effective as fabric softening agents and fibre conditioning agents than the corresponding chemicals which have only one long chain alkyl group in their molecule. Thus, the di (long chain alkyl) quaternary ammonium compounds are more effective as fabric softening agents and fibre conditioning agents than the mono (long chain alkyl) quaternary ammonium compounds. -.

As a consequence of this the di- (long chain alkyl) quaternary ammonium compounds, such as di (hydrogenated tallow) dimethyl ammonium chloride, have been used extensively in the formulation of fabric softening preparations, particularly those for use in domestic laundry applicatons.

Whilst the quaternary ammonium compounds of this type have been satisfactory in so far as their fabric softening properties, they are subject to a number of disadvantages.

A major disadvantage of these quaternary ammonium compounds is that they are not liquid at normal ambient temperatures but are solids or in paste form and ideally require to be melted before being used to prepare dispersions in water. Also, the products of this type ideally require to be dispersed in warm water in order to give storage stable dispersions.

A further disadvantage of this type of quaternary ammonium compound is that the treated fabrics tend to lose their absorbency for moisture because of the presence of the chemical. This results in a tendency to water-proofing of the fabric on repeated treatment with the softening agent.

Another disadvantage of this type of quaternary ammonium compound is the presence within the molecule of an agressive anion, usually a chloride ion, which can cause serious corrosion problems in storage and metering equipment and in the mixing vessels used to prepare the final fabric conditioning products. For this reason it is necessary to use special grades of stainless steel or resin coatings for this equipment. The presence of the chloride ions also excludes the use of this type of quaternary ammonium compound from use in aerosol formulations and in impregnated paper leaves for use during the drying of laundered clothing in a heated tumble dryer.

Yet another disadvantage of this type of quaternary ammonium compound is that it is not possible to prepare stable dispersions with a concentration of quaternary ammonium compound of greater than ca. 10% by weight. With concentrations above this level, the products obtained are not easily dispersed in water and therefore, they are unsuitable for direct use as a fabric softener. Neither are these products suitable for sale as concentrates which the housewife or other end user can readily dilute to the normal use concentration of the chemical, which is usually in the range 4 - 8% by weight of active chemical.

Many alternative quaternary ammonium compounds have been put forward which are claimed to have good fabric softening and fibre conditioning properties without the disadvantage of the di (long chain alkyl) dimethyl quaternary ammonium compounds. Not least amongst these are the quaternary ammonium compounds which contain, within the molecule, a nitrogen containing heterocyclic ring of the imidazoline type.

These imidazoline quaternary ammonium compounds generally fall into two main groups: those with one long chain alkyl group and those with two long chain alkyl groups.

The products which contain only one long chain alkyl group usually contain also a polyether chain produced by reaction of a hydroxyl or amine group with ethylene oxide or its homologues.

The imidazoline quaternary ammonium compounds presently available commercially invariably contain the methosulphte anion and are obtained by using dimethyl sulphate as the quaternizing agent.

In general the quaternary ammonium compounds containing an imidazoline ring structure are more fluid than the di (long chain alkyl) dimethyl quaternary ammonium compounds normally used as fabric softening and fibre conditioning agents.

Futhermore, at an activity level of 75% many are liquid at normal ambient temperatures and can be dispersed in cold or warm water to give stable dispersions which have fabric softening and fibre conditioning properties. Of these the di-tallow imidazolinium quaternary ammonium compounds have the best fabric softening and fibre conditioning properties. In particular 1-methyl-1-alkyl amidoethyl-2-alkyl imidazolinium methosulphate, where the alkyl groups have the chain length distribution of tallow fatty acids, has good softening properties which are in line with those of di-hydrogenated tallow dimethyl quaternary ammonium chloride. This type of imidazoline compound has advantages over the di-hydrogenated tallow dimethyl ammonium chloride quaternaries over and above their fluidity and dispersibility in cold or warm water.

Among these additional advantages can be included better rewet properties and better antistatic properties of the treated fabrics, freeze/thaw stability of the aqueous dispersions and absence of the aggresive chloride ion. This absence of chloride ion widens the scope of application of the product as a fabric softener since it can be used in aerosol formulations and on impregnated paper leaves for use in tumble dryer.

In spite of the many advantages of the l-methyl-l-alkyl amidoethyl-2-alkyl imidazolinium methosulphates compounds, they also have two serious disadvantages. Firstly, their preparation involves the use of the highly dangerous and carcinogenic chemical, dimethyl sulphate. Not only does the use of this chemical require very specialised equipment and handling regulations for its safe use, but there is always a great danger that traces of this highly dangerous dimethyl sulphate may be present in the resultant quaternary ammonium compound.

The other major disadvantage is that the 1-methyl-1-alkylamidoethyl-2-alkyl imidazolinium methosulphate quaternary ammonium compounds give considerably lower viscosity dispersions in water than do the di-hydrogenated tallow dimethyl quaterary ammonium chloride products when dispersed at the same levels of activity. This is particularly noticable with dispersions in water at a level of 5% by weight of the active material; this being one of the preferred levels of activity for the home laundry industry.

It is the object of the present invention to provide a fabric softening or fibre conditioning composition which has the advantages of the dihydrogenated tallow dimethyl ammonium chloride quaternaries and 1-methyl-1-alkylamidoethyl-2-alkyl imidazolinium methosulphate quaternaries but wich overcomes their disadvantages.

According to a first, and broadest, aspect of the invention there is provided a fabric softening or fibre conditioning composition comprising glycerol and either l-ethyl-l-tallow amidoethyl-2-tallow imidazolinium ethosulphate or l-ethyl-l-castor amidoethyl-2-castor imidazolinium ethosulphate.

According to a second, and more preferred, aspect of the invention there is provided a fabric softening or fibre conditioning composition comprising l-ethyl-l-tallow amidoethyl2-tallow imidazolinium ethosulphate, l-ethyl-l-castor amidoethyl-2-castor imidazolinium ethosulphate, and glycerol.

The references to "tallow" and "castor" are to be understood as references to alkyl groups having the same chain length distribution as found in tallow and castor oil respectively.

The imidazolinium compounds derived from tallow and castor oil may be used in the compositions of the second aspect of the invention in a wide range of proportions, for example the weight ratio of these two compounds may be in the range of 99:1 to 1:99. It is however preferred that the weight ratio of tallow derived product to castor oil derived product is in the range 99:1 to 50:50, more preferably 99:1 to 80:20. The glycerol may also be used in any desired amount and serves to assist fluidity and dispersibility of the product.

The preferred method for the preparation of the l-ethyl-l-tallow amidoethyl-2-tallow imidazolinium ethosulphate is by condensation of one molar proportion of tallow triglyceride esters with one and a half molar proportions of diethylene triamine to give glycerol and the diamidoamine of tallow fatty acids, followed by cyclisation to the monoimidazoline and quaternisation with diethyl sulphate. The glycerine liberated in the condensation reaction need not be separated and may thus form at least a part of the glycerine required for the product of either the first or second aspects of the invention.

The l-ethyl-l-tallow amidoethyl 2-tallow imidazolinium ethosulphate may also be prepared by condensation of 2 molar proportions of tallow fatty acids or esters thereof (preferably methyl esters) with one molar proportion of diethylene triamine, followed by cyclisation to the monoimidazoline and quaternisation with diethyl sulphate. When the tallow derived imidazolinium ethosulphate is prepared in this way, it is possible to add the glycerol required for the final composition before the start of the condensation reaction, after the cyclisation or after the quaternisation. The preferred amount of glycerol is two thirds of a mole for every 2 moles of tallow fatty acid or ester used.

The imidazoline ethosulphate derived from castor oil may be prepared by condensation of one molar proportion of castor oil and one and a half molar proportions of diethylene triamine followed by cyclisation and quaternisation with diethyl sulphate. In preparing a composition in accordance with the second aspect of the invention, this reaction may if desired be performed in situ with the production of the tallow derived imidazoline from tallow triglyceride esters tallow acids or esters thereof, or the products obtained by conducting the two reactions separately may be blended together, with the addition of glycerol if this has not already been provided, to give the desired final product after quaternisation.

In a modification of the second aspect of the invention, the 1-ethyl-1-castoramidoethyl-2castor imidazolinium ethosulphate may be replaced partially or wholly by l-ethyl-l- aminoethyl-2-castor imidazolinium ethosulphate. This latter compound may be prepared by condensing 1 molar proportion of diethylene triamine with a third molar proportion of castor oil followed by cyclisation and quaternisation with diethyl sulphate.

The equipment required for the preparation of the products of the invention is a reaction vessel capable of being heated to ca 240"C under atmospheric pressure or alternatively to ca 200"C under reduced pressure (ca 50 mm Hg). The material of the construction of the reaction vessel and agitator is ideally stainless steel but a glass-lined reaction vessel may be used. It is possible to carry out quaternisation with diethyl sulphate in the same reaction vessel. This is in marked contrast to quaternisation with dimethyl sulphate where the regulations require double walled bessels to be used in conjunction with elaborate handling and fume absorption equipment. In addition, with dimethyl sulphate it is necessary to have special decontamination areas for the process personnel engaged in the production.

The statutory requirements and precautions for working with diethyl sulphate are considerably less stringent thus making its use as a quaternising agent very much more attractive than th use of dimethyl sulphate.

The fabric softening or fibre conditioning compositions of the invention may be in the form of a concentrate with isopropyl alcohol or an isopropyl alcohol water mixture.

A composition of l-ethyl-l-tallow amidoethyl-2-tallow imidazolinium ethosulphate and glycerol at 75% concentration in isopropyl alcohol or isopropyl alcohol/water mixture is liquid at normal ambient temperatures and remains pourable down to temperatures below 0 C. The product is dispersible in either hot or cold water to give stable dispersions over a wide range of concentrations.

The incorporation of an imidazolinium ethosulphate derived from the castor oil improves the fluidity of the product and also facilitates the dispersibility of the product in cold water.

The resultant dispersions show excellent softening and fibre conditioning properties on all natural and synthetic fibres. In addition to the soft handle, the treated fabrics also show very good re-wet properties and absence of static. Neither the concentrates nor their dispersions give rise to corrosion problems.

More important, however, is the fact that the 5% active dispersions in water have similar viscosity to those of the 5% active dispersions prepared from dihydrogenated tallow dimethyl amonium chloride with a normal production level sodium chloride content of ca 0.2% by weight.

Thus, with the products of the invention it is possible to prepare 5% active dispersions which have viscosities of the order currently by required by the home laundry industry without resorting to the use of additional thickening agents. Nevertheless, it is possible to use thickening agents of the cellulose ether type to prepare high viscosity dispersions of low activity level.

It is also possible, with the products of the invention, to prepare pourable dispersions in water at activity levels of up to 20%. Furthermore, these dispersions readily redisperse in cold water over the full range of activity levels. It is worthy of note that with dihydrogenated tallow dimethyl ammonium chloride the dispersions of greater than 10% activity are not redispersible in cold water without vigorous agitation.

The invention will be further described by way of example only with reference to the following examples.

Example 1 To an 800 gallon stainless steel reaction vessel equipped with a mechanical agitator, was charged 1333 kg of tallow triglyceride esters and the mass heated to 1950C under vacuum (50mm Hg) to remove dissolved oxygen. The mass was cooled to 100"C and 250 Kg diethylene triamine added slowly over a period of two hours. The temperature was raised to 140"C and held at this temperature for 4 hours. Then the temperature was raised further to 195"C at 50 mm Hg and held at this temperature for 6 hours. The reaction mass was cooled to 600C and at atmospheric pressure 460 Kg isopropyl alcohol was added to the moisture comprising tallow amidoethyl-2-tallow imidazoline and glycerol followed by 366 Kg diethyl sulphate. The mixture was maintained at 600C for 3 hrs.

The resultant product was cooled and further isopropyl alcohol added to give i-ethyl-i-tallow amidoethyl-2-tallow imidazolinium ethosulphate as a 75% active product, which was a liquid product and remained pourable on cooling to below 0 C.

Example 2 In a repeat of example 1, the solvent used to adjust the concentration of the l-ethyl-l-tallow amidoethyl-2-tallow imidazolinium ethosulphate was a mixture of water and isopropyl alcohol so as to give a final solvent content of 20% by weight isopropyl alcohol and 5% by weight of water. The appearance and properties of the product were similar to those of the product from example 1.

Example 3 In a repeat of example 2, 5% by weight of the tallow triglyceride esters were replaced by castor oil.

Example 4 In a repeat of example 2, 10% by weight of the tallow triglyceride esters were replaced by castor oil.

Example 5 bE8ramples 1 - 8 In repeats of examples 1-4 the tallow triglyceride esters were replaced by the tallow fatty acids (2 molar proportions) and glycerine (two thirds of a molar proportion). The resultant products had similar appearance and properties to the products from examples 1 - 4.

Examples 9 - 12 In repeats of examples 1 - 4 the tallow triglyceride esters were replaced by tallow methyl esters 2 molar proportions) and glycerine (two thirds of a molar proportions). The resultant products had similar appearance and properties to the products from examples 1 4.

Example 13 In a repeat of example 2 on l/loooth scale the tallow triglyceride esters were replaced by castor oil (1,460 g) to yield a product comprising l-ethyl-l-castor-amidoethyl-2-castor imidazoline imidazolinium ethosulphate and glycerol. The final product, after adjustment to 75% active strength by weight was a viscous liquid at OOC which dispersed very readily in cold water.

Example 14 In a repeat of example 13 only 730 g castor oil was used to give a molar ratio of castor oil to diethylene triamine of 1:3. The final product (l-ethyl-l-castor amidoethyl (2-castor amidazolinium ethosulphate and glycerol) dispersed readily in water, and on admixture with the l-ethyl-l-tallow amidoethyl-2-tallow imidazolinium ethosulphate gave products with similar performance properties to those obtained by admixture of the latter with the product from example 13.

Example 15 A blend of 90 parts by weight of the product from Example 2 and 10 parts by weight of the product from Example 13 was made.

Example 16 The products from examples 1-4, 13 and 15 at a concentration of imidazolinium ethosulphate of 75% by weight were dispersed in water to give dispersions containing 5%, 71/z% and 10% by weight of the active material. The dispersions were prepared by adding the cold concentrate to cold tap water at 15"C, with gentle agitation by means of a slow speed paddle stirrer. The resultant dispersions had good colour and odour, and remained stable on prolonged storage at ambient temperatures and at 300C. In addition the dispersions had good freeze/thaw stability properties and showed rapid dispersibility in cold and warm water. The dispersions were compatible with a wide range of dyes, perfumes and optical brightening agents normally marketed for use in fabric softener formulations.It was found however, that during the preparation of the dispersions in water the presence of the imidazolinium ethosulphate from castor oil greatly facilitated the ease of dispersion in the cold water. Even at a level of 5% of the castor oil imidazoline the improvement was quite marked.

Example 17 The viscosities of the dispersions in cold water of the products from examples 1-4, 13 and 15 were compared against corresponding dispersions of l-methyl-l-tallow amidoethyl-2tallow imidazolinium methosulphate and dihydrogenated tallow dimethyl ammonium chloride using a BROOKFIELD LVT viscometer.

The dispersion of the l-methyl-l-tallow amidoethyl-2-tallow imidazolinium methosulphate were prepared by addition of the cold quaternary to cold water with stirring. The dispersions of the dihydrogenated tallow dimethyl ammonium chloride were prepared by slow addition of molten quaternary to hot water (600C) with stirring.

The results are shown in following table for determinations at 190C.

Activity level Spindle Speed Viscosity Product % wlw No. rpm. Cp.

Example 1 5 1 3 400 71/2 2 3 2700 10 3 3 11600 Example 2 5 1 3 410 Example 3 5 1 3 370 Example 4 5 1 3 350 Example 13 5 1 3 100 Example 15 5 1 3 350 * di (hy- 5 No. 1 3 300 drogenated 7t/2 No. 2 3 2000 tallow) dimethyl 10 No. 3 3 12800 ammonium chloride l-methyl-l-tallow amidoethyl-2-tallow 5 No. 1 3 90 imidazolinium metho- 71/2 No. 2 3 1000 sulphate * from a typical batch of quaternay ammonium compound with a salt content of ca. 0.2% by weight.

Example 24 The 5% active dispersions in water of the products from Examples 1-4, 13 and 15, the di(hydrogenated tallow) dimethyl ammonium chloride and the 1-methyl-1-tallow amidoethyl 2-tallow imidazolinium methosulphate were compared as rinse water additives in a domestic washing machine for the laundering of cotton fabrics and mixed synthetic fabrics.

From the point of view of softness to the touch, a panel of assessors gave similar ratings to all the products. However, the fabrics treated with imidazolinium products were considered to have a more silky feel than those from the di-(hydrogenated tallow) dimethyl ammonium chloride. The latter were adjudged to have a greasy feel.

In the standard wick test for re-wet properties, the treated fabrics showed significant differences.

The products from examples 1, 2 and the l-methyl-l-tallow amidoethyl-2-tallow imidazolinium methosulphate showed markedly better re-wet properties than those di-hydrogenated tallow dimethyl ammonium chloride as was expected. The product from example 13 (i.e. the imidazolinium ethosulphate from castor oil alone) showed considerably better re-wet properties than these other samples. Furthermore the products from examples 4, 6 and 21 had re-wet properties intermediate between those of the products from examples 1 and 2 and example 18. The improvement in re-wet properties appeared to be roughly proportional to the amount of imidazolinium ethosulphate from castor oil present in the product concentrate.

WHAT WE CLAIM IS: 1. A fabric softening or fibre conditioning composition comprising gylcerol and either l-ethyl-l-tallow amidoethyl-2-tallow imidazolinium ethosulphate or l-ethyl-l-castor amidoethyl-2-castor imidazolinium ethosulphate.

2. A fabric softening or fibre conditioning composition comprising l-ethyl-l-tallow amidoethyl-2-tallow imidazolinium ethosulphate, 1-ethyl-1-castor amidoethyl-2-castor imidazolinium ethosulphate, and glycerol.

3. A composition as claimed in claim 2 wherein the l-ethyl-l-tallow amidoethyl-2tallow imidazolinium ethosulphate was prepared by condensation of mole molar proportion of tallow triglyceride esters with one and a half molar proportions of diethylene triamine to give glycerol and the diamidoamine of tallow fatty acids followed by cyclisation to the monoimidazoline and quaternisation with diethyl sulphate.

4. A composition as claimed in claim 3 wherein the glycerol formed in the reaction between the diethylene triamine and the triglyceride esters was not separated and forms at least a part of the required glycerol in the final composition.

5. A composition as claimed in claim 3 wherein the imidazolinium ethosulphate of castor oil was prepared in situ with the tallow imidazolinium ethosulphate.

6. A composition as claimed in claim 1 or 2 wherein the l-ethyl-l-tallow amidoethyl-2tallow imidazolinium ethosulphate was prepared by condensation of 2 molar proportions of tallow fatty acids or esters thereof with one molar proportion of diethylene triamine, followed by cyclisation to the monoimidazoline and quaternisation with diethyl sulphate.

7. A composition as claimed in claim 6 wherein the l-ethyl-l-tallow amidoethyl-2tallow imidazolinium ethosulphate was prepared from the methyl esters of tallow fatty acids.

8. A composition as claimed in claim 6 or 7 wherein the condensation reaction was conducted in the presence of the required glycerol.

9. A composition as claimed in claim 6 or 7 wherein the required glycerol was introduced after the cyclisation stage or after the quaternisation.

10. A composition as claimed in claim 8 or 9 wherein the amount of glycerol used is two thirds of a mole for every 2 moles of tallow fatty acid or esters thereof.

11. A composition as claimed in claim 2 or in any one of claims 6 to 10 wherein the l-ethyl-l-castor amidoethyl-2-castor imidazolinium ethosulphate was prepared by condensation of one molar proportion of diethylene triamine with a two thirds molar proportion of castor oil followed by cyclisation and quaternisation with diethyl sulphate.

12. A composition as claimed in any one of claims 6 to 11 wherein the l-ethyl-l-castor amidoethyl-2-castor imidazolinium ethosulphate was prepared in situ with the l-ethyl-l- tallow amidoethyl-2-tallow imidazolinium ethosulphate.

13. A composition as claimed in any one of claims 2 to 12 wherein the weight ratio of the l-ethyl-l-tallow amidoethyl-2-tallow imidazolinium ethosulphate to the l-ethyl-l-castor amidoethyl-2-castor imidazolinium ethosulphate is in the range of 99:1 to 1:99.

14. A composition as claimed in claim 13 wherein the weight ratio of the l-ethyl-l- tallow amidoethyl-2-tallow imidazolinium ethosulphate to the 1-ethyl-1-castor amidoethyl2-castor imidazolinium ethosulphate is in the range of 99:1 to 50:50.

15. A composition as claimed in claim 14 wherein the weight ratio of the l-ethyl-l- tallow amidoethyl-2-tallow imidazolinium ethosulphate to the 1-ethyl-2-castor amidoethyl

**WARNING** end of DESC field may overlap start of CLMS **.

Claims (18)

**WARNING** start of CLMS field may overlap end of DESC **. Example 24 The 5% active dispersions in water of the products from Examples 1-4, 13 and 15, the di(hydrogenated tallow) dimethyl ammonium chloride and the 1-methyl-1-tallow amidoethyl 2-tallow imidazolinium methosulphate were compared as rinse water additives in a domestic washing machine for the laundering of cotton fabrics and mixed synthetic fabrics. From the point of view of softness to the touch, a panel of assessors gave similar ratings to all the products. However, the fabrics treated with imidazolinium products were considered to have a more silky feel than those from the di-(hydrogenated tallow) dimethyl ammonium chloride. The latter were adjudged to have a greasy feel. In the standard wick test for re-wet properties, the treated fabrics showed significant differences. The products from examples 1, 2 and the l-methyl-l-tallow amidoethyl-2-tallow imidazolinium methosulphate showed markedly better re-wet properties than those di-hydrogenated tallow dimethyl ammonium chloride as was expected. The product from example 13 (i.e. the imidazolinium ethosulphate from castor oil alone) showed considerably better re-wet properties than these other samples. Furthermore the products from examples 4, 6 and 21 had re-wet properties intermediate between those of the products from examples 1 and 2 and example 18. The improvement in re-wet properties appeared to be roughly proportional to the amount of imidazolinium ethosulphate from castor oil present in the product concentrate. WHAT WE CLAIM IS:

1. A fabric softening or fibre conditioning composition comprising gylcerol and either l-ethyl-l-tallow amidoethyl-2-tallow imidazolinium ethosulphate or l-ethyl-l-castor amidoethyl-2-castor imidazolinium ethosulphate.

2. A fabric softening or fibre conditioning composition comprising l-ethyl-l-tallow amidoethyl-2-tallow imidazolinium ethosulphate, 1-ethyl-1-castor amidoethyl-2-castor imidazolinium ethosulphate, and glycerol.

3. A composition as claimed in claim 2 wherein the l-ethyl-l-tallow amidoethyl-2tallow imidazolinium ethosulphate was prepared by condensation of mole molar proportion of tallow triglyceride esters with one and a half molar proportions of diethylene triamine to give glycerol and the diamidoamine of tallow fatty acids followed by cyclisation to the monoimidazoline and quaternisation with diethyl sulphate.

4. A composition as claimed in claim 3 wherein the glycerol formed in the reaction between the diethylene triamine and the triglyceride esters was not separated and forms at least a part of the required glycerol in the final composition.

5. A composition as claimed in claim 3 wherein the imidazolinium ethosulphate of castor oil was prepared in situ with the tallow imidazolinium ethosulphate.

6. A composition as claimed in claim 1 or 2 wherein the l-ethyl-l-tallow amidoethyl-2tallow imidazolinium ethosulphate was prepared by condensation of 2 molar proportions of tallow fatty acids or esters thereof with one molar proportion of diethylene triamine, followed by cyclisation to the monoimidazoline and quaternisation with diethyl sulphate.

7. A composition as claimed in claim 6 wherein the l-ethyl-l-tallow amidoethyl-2tallow imidazolinium ethosulphate was prepared from the methyl esters of tallow fatty acids.

8. A composition as claimed in claim 6 or 7 wherein the condensation reaction was conducted in the presence of the required glycerol.

9. A composition as claimed in claim 6 or 7 wherein the required glycerol was introduced after the cyclisation stage or after the quaternisation.

10. A composition as claimed in claim 8 or 9 wherein the amount of glycerol used is two thirds of a mole for every 2 moles of tallow fatty acid or esters thereof.

11. A composition as claimed in claim 2 or in any one of claims 6 to 10 wherein the l-ethyl-l-castor amidoethyl-2-castor imidazolinium ethosulphate was prepared by condensation of one molar proportion of diethylene triamine with a two thirds molar proportion of castor oil followed by cyclisation and quaternisation with diethyl sulphate.

12. A composition as claimed in any one of claims 6 to 11 wherein the l-ethyl-l-castor amidoethyl-2-castor imidazolinium ethosulphate was prepared in situ with the l-ethyl-l- tallow amidoethyl-2-tallow imidazolinium ethosulphate.

13. A composition as claimed in any one of claims 2 to 12 wherein the weight ratio of the l-ethyl-l-tallow amidoethyl-2-tallow imidazolinium ethosulphate to the l-ethyl-l-castor amidoethyl-2-castor imidazolinium ethosulphate is in the range of 99:1 to 1:99.

14. A composition as claimed in claim 13 wherein the weight ratio of the l-ethyl-l- tallow amidoethyl-2-tallow imidazolinium ethosulphate to the 1-ethyl-1-castor amidoethyl2-castor imidazolinium ethosulphate is in the range of 99:1 to 50:50.

15. A composition as claimed in claim 14 wherein the weight ratio of the l-ethyl-l- tallow amidoethyl-2-tallow imidazolinium ethosulphate to the 1-ethyl-2-castor amidoethyl

2-castor imidazolinium ethosulphate is in the range of 99:1 to 80:20.

16. A modification of the fabric softening or fibre conditioning composition as claimed in claim 2 wherein said l-ethyl-l-castor amidoethyl-2-castor imidazolinium ethosulphate is replaced by 1-ethyl-1-aminoethyl-2-castor imidazolinium ethosulphate.

17. A fabric softening or fibre conditioning composition as claimed in any one of the preceding claims in the form of a concentrate with isopropyl alcohol or an isopropyl alcohol/water mixture.

18. A fabric softening or fibre conditioning composition as claimed in claim 1, 2 or 16 substantially as hereinbefore described.