WO2006029452A1

WO2006029452A1 - Acylated saccharides and uses thereof

Info

Publication number: WO2006029452A1
Application number: PCT/AU2005/001391
Authority: WO
Inventors: Thavalingam Mailvaganam Pillai
Original assignee: Ip Organisers Pty Ltd
Priority date: 2004-09-14
Filing date: 2005-09-13
Publication date: 2006-03-23
Also published as: WO2006029453A1; MY157665A; TW200608997A

Abstract

The present invention relates to uses of a surface active material including an acylated saccharide. In particular, the invention relates to the use of a surface active material including an acylated saccharide as a surfactant. The acylated saccharide is derived from a carbohydrate source and includes one or more fatty acids. The acylated saccharide may be used in a number of applications in the domestic and industrial environment. It may also be formulated into compositions for use.

Description

ACYLATED SACCHARIDES AND USES THEREOF

FIELD OF THE INVENTION

The present invention relates generally to uses of a surface active material including an acylated saccharide. In particular, the invention relates to the use of a surface active material including an acylated saccharide as a surfactant.

BACKGROUND OF THE INVENTION

Surfactants have found widespread use in a number of applications due to their favourable physico-chemical properties. Surfactants are routinely used in the manufacture of detergents, in emulsification, lubrication, catalysis, oil recovery, and in the preparation of cosmetics and pharmaceuticals. This is because the structural characteristics of surfactants make them useful as surface active compounds and as dispersants and compatibilising agents. Surfactants are compounds that generally have a polar head group and a non-polar alkyl chain. Typically, the polar head group of a surfactant is hydrophilic, while the alkyl chain is hydrophobic. The affinity of the different structural components of the surfactant molecule for different environments therefore confers surface active properties on the surfactant. The nature of the polar head group and the alkyl chain can have influence the final physicochemical properties of the surfactant molecule and hence its use in various applications.

In some circumstances, the polar head group of a surfactant may carry either a positive or negative charge, leading to the production of cationic and anionic surfactants, respectively. Alternatively, a surfactant molecule may contain both anionic and cationic charged groups, thereby resulting in a zwitterionic compound. In other instances, the polar head group of the molecule remains uncharged, thereby providing a non-ionic surfactant. In addition to the charge residing on the polar head group, the length, degree of unsaturation and branching of the alkyl chain, as well as the presence of any substituents may also affect the properties of the surfactant. Non-ionic surfactants are increasingly being used in a number of commercial applications such as in the pharmaceutical, cosmetic, food, textile, petroleum, rubber, polyurethane, bio-pesticide and paint industries. As a class, non-ionic surfactants have a number of physical properties in relation to their mode of action that make them useful in these applications. For example, in contrast to their ionic counterparts, non-ionic surfactants do not disassociate into hydrated ions in aqueous media but rather maintain their structural integrity. Accordingly the surface active properties of non-ionic surfactants are provided by hydration of hydrophilic groups, such as hydroxy, ether, amine or amide groups, that are present in the surfactant. When a sufficiently large number of these hydrophilic constituents are present, the level of hydration is such that water solubility comparable to ionic surfactants is achieved through hydrogen bonding of the hydrophilic groups to water molecules.

The oil and water solubility of non-ionic surfactants therefore often depends upon the relative proportions of the hydrophilic and hydrophobic groups present in the surfactant. It may therefore be possible to control the final properties of the surfactants by controlling the balance between the hydrophilic and hydrophobic components,, which allows for significant tailoring of their properties to be carried out. The molecular structure of non-ionic surfactants also means that they have unusual properties, which make them useful in highly specialised applications. The properties of non-ionic surfactants fall into two broad categories, namely adsorption and self-assembly. Adsorption is the tendency for a surfactant molecule to collect at an interface whereas self-assembly is the tendency for surfactant molecules to organise themselves into extended structures in water. Self-assembly structures include for example, micelles, unilamellar vesicles, bilayers and liquid crystals. The capacity for surfactants to self-assemble may be due to the affinity that the hydrophilic and hydrophobic portions of the molecules have for each other. As a result, aggregates are formed in which the hydrophilic and hydrophobic sections are clustered together. The present invention advantageously provides materials and methods for producing materials that display surfactant-like characteristics or surface active properties. It is desirable that the materials be derived from carbohydrates, in particular, saccharides. Such materials are able to be used in a wide range of industrial applications and may provide a viable alternative to other surfactant systems.

SUMMARY OF THE INVENTION

The inventors have found that surface active materials that include an acylated saccharide can be produced efficiently and in high yield using readily available starting materials. These surface active materials are generally environmentally friendly and biodegradable and are typically non-toxic to humans.

They are also useful as surface active agents.

In one aspect the invention relates to use of a surface active material including an acylated saccharide as a surfactant.

In another aspect, the present invention relates to a method of protecting a surface, including applying a surface active material including an acylated saccharide to the surface. Preferably, the material forms a coating on the surface. In one preferred embodiment, the surface includes fibres. Preferably, the surface is a carpet.

In another preferred embodiment, the surface includes a material selected from the group consisting of wood, metal, plastic, ceramic, concrete, glass, stone and leather. Preferably, the surface includes a metal. More preferably, the metal includes an oxidisable metal. In a further aspect, the present invention provides a method of removing at least one substance from a medium, including contacting the medium with a surface active material including an acylated saccharide.

Preferably, the medium is a solid, liquid or mixtures thereof. In a preferred embodiment, the medium is a liquid and wherein the substance is dispersed in the liquid. Preferably, the liquid is water. In another preferred embodiment, the medium is a solid. Preferably, the solid includes fibres. More preferably, the solid is a carpet.

In a further preferred embodiment, the solid may include a material selected from wood, metal, plastic, ceramic, concrete, glass, stone and leather. Preferably, the solid is a window, bench, wall, ceiling or floor.

In a preferred aspect of the invention, the solid includes a coating. The coating may be a protective or decorative coating.

The substance removed from the medium may be an industrial waste product. The substance may also be a hydrocarbon. Preferably, the hydrocarbon is oil or grease. The substance may further be a substance that produces a stain.

Yet further, the substance may include an ionic species. Preferably, the substance includes a plurality of ionic species. In a preferred embodiment, the ionic species is an anion or a cation. Preferably, the ionic species is selected from the group consisting of chloride, fluoride, sulphate, bromide, calcium, magnesium, potassium, sodium, strontium, boron and mixtures thereof

In one embodiment, the medium may be an emulsion. The present invention also provides a method of compatibilising two or more substances, including adding a surface active material including an acylated saccharide to the substances. Preferably, the method compatibilises a hydrophilic substance and a hydrophobic substance.

In yet another aspect, the present invention provides a method of increasing the optical brightness of a fabric, including applying a surface active material including an acylated saccharide to the fabric.

In the methods of the present invention, it is preferred that the surface active material be present in an amount of from about 0.005% to about 3%, preferably in an amount of from about 0.1% to about 0.5%. It is particularly preferred that the surface active material is present in an amount sufficient to form micelles.

The present invention further provides a composition including a surface active material including an acylated saccharide. Preferably, the composition is a coating composition, a cleaning composition, a compatibilising composition or a brightening composition. In one preferred embodiment, the composition is a cleaning composition.

Preferably, the cleaning composition is a detergent, a stain remover or a degreaser. In another preferred embodiment, the cleaning composition is a treatment composition. In a further preferred embodiment, the cleaning composition is a de-emulsifier.

In another preferred embodiment, the composition is a coating composition. Preferably, the coating composition is a corrosion inhibitor or a fabric protector.

In yet another preferred embodiment, the composition is a compatibilising composition. The compatibilising composition may be an emulsifier. The compatibilising composition may also be a wetting agent.

Preferably, the surface active material is present in the compositions of the invention in an amount of between about 0.01% to 10%, more preferably, from about 0.005% to about 3% by weight of the composition. In a preferred embodiment, the surface active material is present the compositions of the invention in an amount sufficient to form micelles.

The surface active material can be produced efficiently from readily available starting materials thus providing a relatively cheap source of these materials.

Carbohydrates are desirable as a raw material for the preparation of the surface active material, as carbohydrates are readily available, relatively inexpensive and easy to source.

BRIEF DESCRIPTION OF THE FIGURES

Figure 1(a) shows a photograph of the surface active agent of example 1 dissolved in potable water at a concentration of 10mg/ml at a magnification of 100x under polarised light and shows a unilamellar vesicle.

Figure 1(b) shows a photograph of the surface active agent of example 1 dissolved in potable water at a concentration of 10mg/ml at a magnification of 2Ox under polarised light with a dark field and shows a multilamellar vesicle. Figure 1(c) shows a photograph of the surface active agent of example 1 dissolved in potable water at a concentration of 10mg/ml at a magnification of 2Ox under polarised light d shows a multilamellar vesicle. Figure 1(d) shows a photograph of the surface active agent of example 1 dissolved in potable water at a concentration of 10mg/ml at a magnification of 2Ox under polarised light and shows a unilamellar vesicle.

Figure 1(e) shows a photograph of the surface active agent of example 1 dissolved in potable water at a concentration of 10mg/mi at a magnification of 2Ox under polarised light and shows a multi-lamellar vesicle.

Figure 2 shows a graph of surface tension versus concentration of surface active agent, which illustrates the critical micelle concentration of a surface active agent.

DETAILED DESCRIPTION OF THE INVENTION

Various terms that will be used throughout the specification have meanings that will be well understood by a skilled addressee. However, for ease of reference some of these terms will now be defined.

As used herein reference to a percentage of a component in a reaction mixture or composition refers to the percentage by weight unless otherwise specified.

Acylation - this is a chemical transformation which substitutes the acyl group (RCO-) into a moiety generally for an active hydrogen. Acylation of a hydroxy group forms an ester whereas acylation of an amino group forms an amide. A molecule that has been subjected to acylation is said to have been acylated.

Fats - the fats are esters of fatty acids with glycerol having the general formula (R₁COO)CH₂-CH(OOCR₂)CH₂(OOCR₃). In the formula R₁, R₂ and R₃ may be the same fatty acid member but in general the fats are mixed glycerols with each residue being different. The fatty acids present in the greatest quantity are typically oleic, palmitic and stearic acids. The fats are generally seen as having a melting point of greater than 20° atmospheric pressure.

Lipolytic material - A lipolytic material has the ability to hydrolyse fats into fatty acids and glycerol. A preferred example of a lipolytic material is a lipase. Oils - these are glycerides of fatty acids as described for fats but having a melting point of less than 20° atmospheric pressure. Vegetable oil - vegetable oils are oils obtained from leaves, fruit or seeds of plants.

Animal oil - oils derived from animals.

Fatty acids - monobasic acids containing only the elements carbon, hydrogen and oxygen and consisting of a straight chain organic radical attached to the carboxyl group. Fatty acids may be saturated, monounsaturated, or polyunsaturated depending on the number of carbon carbon double bonds in the organic radical.

The saturated fatty acids have the general formula C_nH₂nθ₂ with methanoic and ethanoic (acetic) acid being the lowest members of the series which includes palmitic and stearic acid.

The oleic acid series with one double bond has the general formula C_nH_2n-2O₂ with the acrylic acid being the lowest member.

The linoleic series has two double bonds and the general formula C_nH_2n-4O₂. The linolenic series has three double bonds and the general formula

Fatty acids with more than three double bonds are general classed as polyunsaturated fatty acids.

Examples of fatty acids are capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid and alpha linolenic acid. Saccharides - These are sugars and include monosaccharides, di-saccharides, tri- saccharides, oligosaccharides and polysaccharides.

Polysaccharides - A polysaccharide is any molecule that can be hydrolysed to form more than one saccharide molecule.

Surface Active Materials - These are materials which contain structurally dissimilar groups with opposing solubility tendencies such as water soluble and water insoluble groups. When dissolved in water or some other solvent these materials are adsorbed at the interface between the solution and a phase in contact with it (air, another liquid, soiled material) and modify its properties.

Compatibilising - This is a process by which two or more substances having limited solubility or compatibility with each other under a given set of conditions due to differences. in chemical and/or physical properties are able to be made more compatible with each other.

Micelle - A micelle is a cluster or group of associated molecules. Micelles may be represented as a globular cylindrical or ellipsoidal cluster of individual surfactant molecules in equilibrium with its monomers.

Critical Micelle Concentration (CMC) - The surfactant concentration at which a micelles form in solution corresponds to the critical micelle concentration. At surfactant concentrations below the CMC, the surfactant molecules are loosely integrated into the water structure. In the region of the CMC, the surfactant-water relationship is changed in such as way that surfactant molecules begin to aggregate or self-assemble into structures having micelles on the interior and surfactant monolayers at the surface.

The present applicants have developed a new surface active material that contains one or more acylated saccharides and an improved technique for the production of the surface active material. The surface active material may be used in a number of applications as a viable alternative to other surfactant systems.

Surface active materials of the Invention

In one aspect, the present invention relates to a surface active material including an acylated saccharide. In a preferred embodiment the surface active material includes one or more acylated saccharides. The saccharide may be mono- acylated, di-acylated, tri-acylated or polyacylated with a mono-acylated saccharide being particularly preferred.

The material preferably contains a plurality of different acylated saccharides, preferably at least two, more preferably at least three, most preferably at least four distinct acylated saccharides. For example this may be achieved by including a plurality of saccharide components in the synthesis of the material in which case there will be at least two (and possibly more) acylated saccharides present in the final material. More typically, however, a single saccharide is used and a plurality of acylated saccharides is produced by reacting the saccharide with a plurality of different acid sources. This is especially the case where the material is produced by the process of the present invention.

The acyl component of the acylated saccharide is preferably derived from an organic acid, more preferably a fatty acid, particularly a fatty acid derived from fats on oils or combinations thereof. The fatty acid preferably has from 1 to 24 carbon atoms, more preferably from 4 to 20 carbon atoms, most preferably from 8 to 16 carbon atoms. The fatty acid preferably has 0 to 4 unsaturations, more preferably 0 to 2 unsaturations, most preferably 0 or 1 unsaturations. Preferably the fatty acid is selected from the group consisting of capric acid, caproic, caprylic, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, and α-linolenic acid.

In one preferred embodiment of the invention the acyl component is derived from animal fats or vegetable fats or mixtures thereof. In another preferred embodiment the oils are selected from animal or vegetable oils or mixtures thereof. In a particularly preferred embodiment the acyl component is derived from the group consisting of beef tallow, human butter fat, beef butter fat, canola oil cocoa butter, cod liver oil, coconut oil, corn oil, cotton seed oil, flax seed oil, grape seed oil, pork fat, linseed oil, olive oil, palm oil, palm kernel oil, peanut oil, safflower oil, sesame oil, soy bean oil, sunflower oil and mixtures thereof. It is particularly preferred that the acyl component is derived from palm oil and/or coconut oil or a pure source of lauric acid, caproic acid, caprylic acid, or myristic acid.

In the process of manufacture of materials of this type the acyl source is typically mixed to determine the fatty acid profile of the final material. A number of different acyl sources can be used in this way in order to arrive at a plurality of acylated saccharides in the final product.

Any suitable saccharide or saccharide containing material may be used as the saccharide component of the material. Preferably the saccharide is a polysaccharide or polysaccharide containing material. The polysaccharide can be a disaccharide (such as sucrose or maltose) a tri-saccharide, a tetrasaccharide or a higher polysaccharide, or a mixture thereof Examples of polysaccharides include starches and their derivatives, cellulose and its derivatives, amino sugars and the like. It is preferred that the saccharide contains one or more amino groups.

In one preferred embodiment the polysaccharide containing material includes chitosan. It is particularly preferred that the material is chitosan. In another preferred embodiment the polysaccharide containing material is rice husk.

These materials may be used alone or may be used in combination with other polysaccharide sources.

The properties of the material may be controlled by varying the type of fatty acid acyl group used. For example, in order to improve anti-microbial properties of the material it is preferred that the fatty acid chain length is C₈-C₁₄. Similarly, in order to achieve a high detergency or wetting properties it is preferred that a chain length of C₁₂ to C₁₅ is used.

Accordingly, depending on the application it is preferred that the material include more than one acylated saccharide. Thus one acylated saccharide may contain a Ce-C₁₄ fatty acid whilst another may contain a C₁₂-C₁₅ fatty acid. By varying the fatty acid profile of the acylated saccharide one can therefore produce either a material with high detergency or a material with antimicrobial properties, or a material that has both these properties. In a preferred embodiment the acyl component of the material has the following free fatty acid profile upon GC MS analysis of the material:

Fatty Acid Percentage of Acyl Component

C6:0 0.0% to 0.3%

C8:0 0.0% to 5.0%

C10:0 0.0% to 5.0%

C12:0 10.0% to 60%

C14-.0 5.0% to 20.0%

C16:0 5.0% to 15.0%

C18-.0 0.0% to 4.0%

C18-.1 10.0% to 30.0%

C18-.2 0.0% to 25.0% C18:3 0.0% to 1.0%

C20:0 0.0% to 1.0%

C22:0 0.0% to 1.0%.

In a particularly preferred embodiment the acyl component of the material has one of the free fatty acid profiles provided in Table 4 upon GC MS analysis of the material.

A skilled addressee would readily be able to adjust the free fatty acid profile in order to arrive at a surface active material having the desired properties.

The properties of the material may also be improved by blending it with other ingredients. Thus for example it may be blended with a fragrance to improve the organoleptic properties, colours to provide the desired colour and the like.

In a further preferred embodiment the material is blended with rice husks.

The amount of rice husks blended well depend on the final form of the desired product but is preferably from 0.5% to 15wt.%, more preferably from 1.5% to 10 wt.%, even more preferably 2% to 8 wt.%, most preferably 4% to 6 wt.% of the surface active agent. The rice husk preferably has been ground to a size of from

4-25 micron, more preferably from 6-21 micron, even more preferably 8-17 micron.

By incorporating an amount of rice husk, the properties of the rice husk may be incorporated into the surface active material to complement the activity of the material. For example, the anti-microbial properties of the rice husk may be incorporated into the material.

Process of production of surface active materials of the invention

The invention also relates to a method of producing a surface active material that includes an acylated saccharide, the method including: (a) providing a glyceride hydrolysate containing one or more free fatty acids or derivatives thereof, and (b) allowing the free fatty acids or derivatives thereof to react with a saccharide or a saccharide containing material.

The glyceride hydrolysate may be pre-formed or it may be prepared by at least partially hydrolysing a glyceride containing material to form free fatty acids or derivatives thereof. The glyceride containing material used in the process can be of any suitable type and the glyceride containing material is chosen based on a number of factors. These include cost, availability, and the free fatty acid profile desired in the final product. The glyceride containing material is preferably selected from the group consisting of fats and oils or mixtures thereof. In one preferred embodiment the fats are selected from animal fats or vegetable fats or mixtures thereof. In another preferred embodiment the oils are selected from animal or vegetable oils or mixtures thereof. Natural fats or oils of this type typically consist of glycerol esters of linear saturated or unsaturated fatty acids with an even number of carbon atoms. The chemical nature of the glycerine ester will depend upon the material but in general these can be separated into three groups:

1. Vegetable fats and oils which principally vary in the ratio of caproic, caprylic, lauric, myristic, oleic and linolenic acid ratios.

2. Animal fats and oils composed of primarily palmitic and oleic acids.

3. Vegetable oils with a high content of lauric and myristic acid.

The full acid composition of common fats and oils is given in Table 1. As can be seen, the fatty acid profile of common fats and oils varies greatly. As such the identity of the glyceride containing material can be chosen to introduce certain fatty acids into the final surface active agent.

For example, if one wishes to incorporate a high level of oleic acid into the material a good choice of glyceride containing material is canola oil. Approximately 62% of the fatty acids in canola oil is oleic acid and so if their oil is used it is likely that oleic acid will end up in the material. In contrast, if it is determined that lauric acid is a desired free fatty acid then coconut oil or palm kernel oil, both of which are high in this fatty acid, should be used. A skilled worker could use the information in Table 1 to readily determine the appropriate glyceride or combination thereof to introduce the desired free fatty acids into the material using the process of this invention. TABLE 1

Fatty Acid Composition of Some Common Edible Fats and Oils

Percent of Total Fatt Acids

W

In a particularly preferred embodiment the glyceride containing material is selected from the group consisting of beef tallow, human butter fat, beef butter fat, canola oil, cocoa butter, cod liver oil, coconut oil, corn oil, cotton seed oil, flax seed oil, grape seed oil, pork fat, linseed oil, olive oil, palm oil, palm kernel oil, peanut oil, safflower oil, sesame oil, soy bean oil, sunflower oil, and mixture thereof. A particularly preferred glyceride containing material is palm oil.

These materials are useful sources of free fatty acids as they are relatively cheap and their fatty acid analysis on hydrolysis is reasonably well understood. In general all these glyceride containing materials are readily available and may be sourced commercially. The amount of glyceride containing material used will be determined on the basis of the amount of free fatty acid required to be generated for the saccharide or saccharide containing material to be used. In general it will be readily apparent to a skilled addressee how to determine the amount of glyceride containing material. In general, however, it is preferred that the glyceride containing material is employed in slight excess of that required to produce the mono-acylated of the saccharide.

In a preferred embodiment the amount of glyceride containing material constitutes between 40% to 60% of the reaction mixture, more preferably 45 to 55%, even more preferably 48% to 52% of the reaction mixture. The glyceride material can be a single fat or oil or may be a mixture of fats and oils depending on the free fatty acid profile being introduced into the surface active agent.

The step of partially hydrolysing the glyceride containing material to form 25 free fatty acids is typically conducted in a non-interfering solvent. Any of a number of solvents can be used. In general a solvent will be considered a non-interfering solvent if it does not inhibit or participate in the hydrolysis/acylation processes. It is desirable, however, that the solvent is one in which the surface active agent, once formed is not soluble. This can be determined by trial and error in each instance.

A preferred solvent is an organic solvent, preferably an alcohol such as ethanol, methanol, propanol or butanol, more preferably tertiary butyl alcohol. It is found that tertiary butyl alcohol is a particularly preferred solvent as it is miscible with most fats and oils but the surface active agents once formed are not soluble in it. An advantage of this is that the product can be isolated by filtration as discussed later. The amount of solvent (if used) will vary on a case by case basis. The amount of solvent is typically from 10% to 30% of the total reaction mixture, more preferably from 14% to 26%, most preferably from 17% to 19%.

As such it is typical that the fat or oil is admixed with the solvent and agitated to form a homogeneous solution or mixture (depending on the solubility of the fat or oil in the solvent) before addition of the other ingredients. Alternatively all the solid ingredients are added to the reaction vessel followed by addition of the liquid ingredients. It is preferred that the solvent is one in which the fat(s) and/or oil(s) chosen are soluble.

Hydrolysis of the glyceride containing material can occur in any way well known in the art for the hydrolysis of a glyceride to form a free fatty acid or derivative thereof. It is preferred, however, that hydrolysis is achieved by addition of a lipolytic material to a glyceride containing material in the solvent chosen. Any lipolytic material can be chosen with the identity of the lipolytic material being determined based on the glyceride containing material. As would be well known to a skilled addressee, different lipolytic materials have different selectivities. Some lipolytic materials have broad spectrum activity and can be used with any glyceride containing material. Other lipolytic materials have quite high selectivity and are selective for certain fatty acids. The choice of lipolytic material will thus depend on the choice of glyceride containing material and the fatty acid to be acylated onto the saccharide. In general this will cause little difficulty as commercial lipase suppliers typically provide Free Fatty Add Profiles for their lipase products which indicate their selectivity (if any).

The lipolytic material used in the present invention may be any lipolytic material well known in the art. An example of suitable lipolytic materials are enzymes that may be synthetic or derived from animal, vegetable, bacterial or mould sources. A particularly suitable lipolytic material is lipases, particularly lipases of animal, vegetable, bacterial or moulds origin. For example any commercial lipase preparation containing predominantly lipase activity may be used. These may be used either in their crude form or may be used in partially or wholly purified form.

The identity of the lipolytic material will typically vary with the identity of the glyceride containing material. A skilled worker will in general be able to determine a suitable lipolytic material for the glyceride chosen as discussed above.

A particularly preferred lipase is a lipase derived from Candida Antarctica of Thermomyces lanuginorus.

The amount of lipase used depend on a number of factors including the nature of the glyceride containing material, the concentration of the glyceride containing material in solution, the desired temperature of the lipolytic reaction, the concentration or activity of the lipase, and the pH of the reaction mixture. In general a skilled worked will easily be able to choose a suitable amount of lipase to achieve the desired result. Nevertheless the amount of lipase is typically of the order of 4% to 17%, more preferably 6% to 15%, even more preferably 8% to 13%, most preferably 8% to 11 % of the reaction mixture.

The hydrolysis of the glyceride containing material may be only partial or it may be carried out such that complete hydrolysis occurs. The hydrolysis is typically carried out such that the glyceride is at least 40% hydrolysed, even more preferably at least 60% hydrolysed, even more preferably at least 60% hydrolysed, more preferably 80% hydrolysed, even more preferably at least 90% hydrolysed. As would be clear to a skilled addressee a higher level of hydrolysis is preferred as this leads to a greater atom efficiency and thus higher yields of polysaccharide ester for the same amount of glyceride used. As such this is more commercially attractive. The level of hydrolysis may be followed using standard analytical techniques (such as HPLC, GLC etc.) or the process may be carried out for a sufficient time to ensure adequate hydrolysis.

The process is preferably conducted in the presence of a base. The base may be an organic or an inorganic base. Examples of suitable inorganic bases include sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, calcium carbonate, and magnesium carbonate. Examples of suitable organic bases are sodium acetate and potassium acetate.

The base is preferably sodium acetate. The amount of base is typically of the order of 10% to 30 wt.% based on the total reaction mixture, more preferably 8% to 20 wt.%, most preferably 10% to 13 wt.%.

The process can be carried out at any suitable temperature. The temperature chosen will depend on a number of factors including the rate of reaction required, the amount of lipase, the type of lipase, the concentration of the reaction mixture and the like. It is found, however, that the temperature should be chosen to minimise side reactions occurring. For example it is found that many glyceride containing materials are sensitive to elevated temperature. Whilst not wishing to be bound by theory, it is felt that those glycerides that contain fatty acid chains with either conjugated double bonds or a large number of double bonds are susceptible to side reactions (such as oxidation). As such it is preferred that the temperature is from 2O⁰C to 60⁰C, more preferably from 3O⁰C to 50°C, even more preferably from 35°C to 44°C, most preferably about 38⁰C.

The process is typically carried out for a period of from 3 to 24 hours, more preferably from 6 to 15 hours, more preferably from 8 to 11 hours, most preferably for about 8 hours.

Any suitable saccharide or saccharide containing material can be used although it is preferred that it is a polysaccharide or polysaccharide containing material. The polysaccharide can be a disaccharide (such as sucrose or maltose, a tri-saccharide, a tetra-saccharide or a polysaccharide derived from sago). Examples of polysaccharides that may be used in the surface active agent of the invention include starches and their derivatives, cellulose including derivatives, amino sugars and the like. Of course a mixture of difficult polysaccharides may also be employed. When this is done it ensures that the material includes a plurality of acylated polysaccharides as the polysaccharide components are different. The amount of the saccharide or saccharide containing material utilised is from 0.5% to 15 wt.%, more preferably from 1.5% to 10 wt.%, even more preferably from 2% to 8 wt.%, most preferably from 4% to 6 wt.%. It is preferred that the saccharide contains one or more amine groups. In one preferred embodiment the polysaccharide is chitosan. Chitosan is a polysaccharide material product that is derived from chitin and is available commercially. Any grade of chitosan may be used but it is found that the purer the chitosan the greater the purity of the final product. The polysaccharide is found in the exoskeleton of shellfish such as shrimp and crabs. The structure of chitosan is as follows:

In another preferred embodiment the polysaccharide containing material is rice husk. It is found that if the saccharide containing material is rice husk then the final product will have properties of the rice husk. Whilst the composition of rice husks typically vary it has the following general composition.

Chemical and Physical Composition rice husk

Crude protein, % N x 6.25 1.9 —3.0

Crude fat, % 0.3—0.8

Crude fiber, % 34.5^5.9 Available carbohydrates, % 26.5—29.8

Crude ash, % 13.2—21.0

Silica, % 18.8—22.3

Calcium, mg/g 0.6 — 1.3

Phosphorus, mg/g 0.3 — 0.7 Neutral detergent fiber, % 66 —74

Acid detergent fiber, % 58-62

Lignin, % 9—20

Cellulose, % 28—36

Pentosans, % 21 —22 Hemicelluloses, % 12

Total digestible nutrients, % 9.3 — 9.5

Table 2 Amino A Acciidd Analysis in Rice Husk

Amino^" Acid (%) Amino Acid (%)

Aspartic acid 0.09 Tyrosine 0.86

Glutamic acid 0.42 Valine 0.35

Serine 0.23 Methionine (MET) 0.23

Glycine 0.60 Cystine (CYS.CYS) 0.03

Histidine 0.00 lsoleucine 0.07

Arginine 0.15 Leucine 0.33

Threonine 0.59 Phenylalanine 0.39

Alanine 0.78 Tryptophan 0.06

Lysine 0.15

It is preferred that the saccharide is not sucrose. The step of hydrolysing the glyceride containing material to form free fatty acids and reacting the free fatty acids with the saccharide or saccharide containing material can occur sequentially or simultaneously.

Thus, for example, if desired one could partially hydrolyse glyceride containing material to form a fatty acid containing solution. The fatty acids could in theory be isolated from the solution or the solution then reacted further. For example following the completion of hydrolysis the solution could then be contacted with a saccharide or saccharide containing material in order to allow the free fatty acids or derivatives thereof to react with free hydroxy groups (or amine groups if present) on the polysaccharide. It is found, however, that it is not desirable to carry out the process sequentially or to isolate the free fatty acids. The step of isolation of the free fatty acids is undesirable as this is difficult and quite expensive to achieve in a cost-effective manner. The difficulty with carrying out the steps sequentially is that as the concentration of free fatty acids and glycerol increases there is the tendency for the fatty acids to react with the free hydroxy groups on the glycerol thus leading to re-esterification of the glycerol and formation of the starting glyceride. This is clearly undesirable and should be avoided. As such whilst sequential steps are possible they are not preferred.

Accordingly it is preferred that the steps are carried out simultaneously wherein the saccharide or saccharide containing material is present when the glyceride containing material is hydrolysed and the free fatty acids liberated. This ensures that as the free fatty acids are liberated they will have the tendency to esterify hydroxy groups from the polysaccharide rather than re-esterifying the glycerol. Accordingly in a further aspect there is provided a method of producing a material including one or more acylated saccharides, the method including partially hydrolysing a glyceride containing material to form free fatty acids and derivatives thereof in the presence of a saccharide or saccharide containing material. This ensures that as the free fatty acids are liberated in the hydrolysis reaction they are available for reaction with free hydroxy groups on the saccharide. The best way of achieving this is to admix all ingredients and add the lipase last once the other ingredients had been mixed.

During the process of the invention it is preferred that the components are agitated rapidly to ensure adequate mixing of the components during reaction. If mixing is not sufficient the rate of reaction slows considerably.

Upon completion of reaction the product can be isolated in a number of ways. It is typically found, however, that the product precipitates as it is produced and it can thus be isolated by filtration. In order to facilitate precipitation a solvent in which the product is not soluble such as t-butanol typically is added to produce a crude precipitate. This can then be isolated using techniques well known in the art.

Following removal of the crude material by filtration the filtrate can be recycled. It is found that the filtrate will typically contain unreacted starting materials, lipase and solvent. This can be resubjected to the process of the invention, typically with addition of further substrate. It is found that it is preferable to dry the filtrate to remove any water before resubjecting it to the process.

The crude precipitate typically has surface active properties and may be used as a surfactant. It may be partially purified by washing with a solvent in which the surface active agent is not soluble. For example it is found that washing of the crude with tertiary butanol will serve to remove any excess glyceride containing material from the product.

If a higher level of purity is required the crude material may be further washed with TBA or any solvent. Increased purity can be achieved by adding the crude material to water followed by filtration to remove water insoluble impurities. It is found that the material is soluble in water whereas the other ingredients in the mixture are not. As such addition of the crude precipitate to water allows for the removal of these insoluble ingredients. A typical process would involve addition of approximately 100g of crude to 5 litres of water, filtration of the solution leading to removal of the solids leading to a solution with a concentration of 4 g/L of the surface active agent. Use of Surface Active Material

The surface active material of the invention may be used in a number of applications, including pharmaceutical and industrial applications.

In one aspect, the present invention relates to the use of a surface active material including an acylated saccharide as a surfactant. The ability of the material of the invention to act as a surfactant is due to the favourable surface active properties exhibited by the material. Surfactant behaviour may be ascertained by observing micelle formation and any transitions that may signify a critical micelle concentration (CMC). Micelles are aggregates of surfactants that assemble together in a solution. They can have a wide range of size and shapes that will often depend on the molecular structure of the surfactant molecules as well as their concentration. Micelles are usually only formed at concentrations above the CMC. The CMC may be marked by sharp transitions in physical parameters such as the surface tension of the solution, conductivity and turbidity, which are indicative of a change in properties occurring as the micelles form. As seen in Figure 2, the material of the invention is capable of forming micelles, and for a 2% solution containing an acylated saccharide, a critical micelle concentration (CMC) was observed at a concentration of about 0.13% to 0.25%, as measured by a change in surface tension. When the surface active material of the invention is used as a surfactant, it is preferred that the surface active material be used in a concentration that will provide a desirable surfactant or surface active effect. In this regard, it is preferable that the concentration of surface active material be at or close to the critical micelle concentration (CMC). The CMC may vary for any given surface active material at any given concentration in solution and the person skilled in the art may readily ascertain the CMC using standard techniques.

The surfactant properties of the surface active material enable the material to be used in a wide of applications where the presence of a surfactant is desired. In addition, the generally environmentally friendly, biodegradable and non-toxic nature of the surface active materials allow these materials to be employed in a wide range of applications across a number of industries, including research and industrial applications. These applications include for example, industrial processes, the manufacture of consumer goods, the preparation of pharmaceutical and cosmetic formulations and in the manufacture and preparation of food products. In another aspect, the present invention relates to a method of protecting a surface, including applying a surface active material including an acylated saccharide to the surface.

In many domestic and commercial situations, it is often desirable to be able to protect a surface from damage or loss of appearance. Damage may arise when a substance undergoes a chemical reaction with a surface. For example, oxygen or salts, such as the sodium chloride in seawater may react with metal, leading to corrosion of the metal. Such reactions weaken the metal and render the metal susceptible to further degradation. Damage to a surface may arise when unwanted substances come into contact with and subsequently soil a surface. For example, fabric articles such as clothing, furniture or floor coverings may absorb substances that could lead to staining of the fabric, thereby damaging the appearance of the article and loss of aesthetic appeal.

In order to protect a surface, some form of barrier material may be used. The barrier material may act to the separate the surface from any undesirable substances and thereby inhibit any chemical reactions or contact occurring between the surface and the substances. The applicants have found that surface active material of the invention may act as a barrier material and therefore be used to protect a surface.

The surface active material of the invention is conveniently applied to the surface in a manner that allows the surface active material to form a coating or layer on the surface. Preferably, the surface active material forms a continuous film on the surface. The coating or film may be applied to the surface in any manner, including for example, wiping, spraying, painting or dipping.

The surface active material of the invention may be applied to any suitable surface. In one preferred embodiment, the surface includes fibres. Such surfaces include for example, clothing, furniture, window hangings such as blinds and curtains and floor covering such as rugs and carpets. Preferably, the surface is a carpet.

In another preferred embodiment, the surface includes a material selected from the group consisting of wood, metal, plastic, ceramic, concrete, glass, stone and leather. Preferably, the surface includes metal. More preferably, the metal includes an oxidisable metal.

Upon application to a surface, the surface active material of the invention is able to protect the surface from dirt, soiling, stains and the like. As a result, when substances are spilled, dropped or smeared onto the surface that has been treated with the surface active material of the invention, the surface is able to resist any staining by the substance due to the presence of the protective surface active layer.

The surface active material may also act as a corrosion inhibitor by providing a protective coating that inhibits the reaction of substances such as oxygen or salt with surfaces that are susceptible to corrosion.

When the surface active material is used to protect a surface, the surface active material may be applied at any concentration that will enable it to achieve the advantages of the invention. Preferably, the concentration of surface active agent applied to a surface is from about 0.005% to about 3% by weight, more preferably from about 0.1% to about 0.5% by weight, even more preferably from about 0.13% to about 0.25% by weight. The surface active material is typically applied in the form of an aqueous composition.

In another aspect, the present invention relates to a method of removing a substance from a medium, including contacting the medium with a surface active material including an acylated saccharide.

The substance is an element of matter and may be a solid, a liquid or mixtures thereof. The substance may be any substance that is desired by the user to be removed from the medium. The type and nature of the substance that is removed will often be dependent on the medium and the application. The removal assists to separate the substance from the medium and may result in partial or complete purification of the medium. Exemplary substances include dirt, stains, odourous compounds, ionic species such as salts, industrial waste products such as solids from sludge and hydrocarbons such as grease and oil.

The medium is an environment that carries or incorporates the substance. The medium may be a solid, liquid or mixtures thereof. Preferably, the medium is a solid or a liquid. However the medium may also be a mixture of at least one solid and at least one liquid, two or more solids or two or more liquids. Examples of mixtures include suspensions and emulsions. Depending on the nature of the medium, the substance may be dispersed, suspended or dissolved in the medium. The substance may also be carried by the medium. In one embodiment, the medium is a liquid. Preferably, the substance is dispersed in the liquid. Examples of liquids having a substances dispersed therein include emulsions, such as oil-in-water or water-in-oil emulsions, in which a liquid substance is dispersed in a liquid medium, suspensions, in which solid particles are dispersed in the liquid medium and solutions, in which a solid or a liquid substance is dissolved in the liquid medium. The medium may include any liquid, and the present invention is not limited in application to any type of liquid medium. Suitable liquids include for example, petroleum, oil, water, milk, fruit juice and solvents. Preferably, the liquid is water.

When the medium is a liquid, the substance may be emulsified or suspended in the liquid. As a result, it is often difficult to separate the substance from the liquid. The separation of substance and liquid may be desired in many applications in order to purify the substance or the liquid for further processing. The material of the invention may therefore be used as a de-emulsifier to separate out and remove substances from an emulsified mixture or suspension. For example, an oil-in-water emulsion generally involves the fine suspension of droplets of oil in a water environment. The surface active material of the invention may be used to disrupt this emulsion, thereby releasing the oil droplets and allowing the oil to coalesce into a homogeneous phase. The components of the emulsion may then be separated out into two distinct phases; an oil phase and a water phase. This ability to separate components of a complex mixture into constituent phases may be desirable in applications such as sludge purification and crude oil extraction.

In another embodiment, the medium is a solid. A solid is generally considered to be any mass that does not have liquid or gaseous properties. The medium may include any solid. The solid may be of two-dimensions, such as a surface, or it may be a three-dimensional mass. The solid may also consist of a single mass, such as a piece of wood, or it may be a collection of masses.

When the medium is a solid, the substance is generally carried by the medium. In this regard, the substance may sit on or be adhered to the solid, be mixed in with the solid or be absorbed into at least a portion of the solid. For example, if the substance is a liquid, the liquid may taken up by the solid medium and thereafter held in the medium. In comparison, where the substance is a solid, the substance may be present in an admixture with the solid medium.

In a preferred embodiment, the solid includes fibres. Such solids include for example, clothing, furniture coverings, window hangings such as blinds and curtains and floor covering such as rugs and carpets. Preferably, the solid is a carpet.

When the solid includes fibres, the material of the invention may be used as a cleaner to remove dirt, stains and other undesirable substances that may have been spilled or smeared onto the solid. It is believed that the surfactant characteristics of the acylated saccharides enable the material of the invention to work as an effective cleaning material. The material of the invention may be applied to the fibres, allowed to react with the dirt or stain in order to remove the undesirable substance from the fibres then be washed away. The cleaner may be used to clean any suitable solid that includes fibres. A preferred cleaner is a carpet cleaner.

In another preferred embodiment, the solid includes a material selected from the group consisting of wood, metal, plastic, ceramic, concrete, stone, glass, leather and mixtures thereof. Where the solid has three-dimensional form, it may exist in any form. Suitable forms that are generally encountered in the domestic or commercial environment include for example, pieces of furniture or machinery. The solid may also be a surface having two-dimensional form. Where the solid is a surface, the solid is preferably a window, bench, wall, ceiling or floor.

The material of the invention may be used to remove substances from the two or three-dimensional solids. For example, the surface active properties of the acylated saccharides may allow the material of the invention to be used as a degreaser, thereby removing hydrocarbons such as grease or oil from machinery parts and the like. The material of the invention may also be used to clean surfaces, such as floors, windows and benches. In such applications, the acylated saccharide may be assist in lifting and emulsifying dirt and other matter from a surface in the home or commercial environment, for effective cleaning of that surface.

In another embodiment, the substance may be a product of industrial processing. Preferably, the substance is an industrial waste product, such as the solids that are produced during sludge purification. The substance may also be an environmental contaminant. These environmental contaminants may include for example, hydrocarbons, oil, minerals, pesticides, inorganic and organic products, heavy metals and the like. The material of the invention may advantageously be used to remove at least a portion or alternatively, all of these substances present in a medium in order to purify the medium before further treatment or discharge of the medium into the environment.

Where the medium is a solid, the medium may also include a coating. The coating may be a protective or decorative coating. Such coatings are generally used to protect and/or enhance the aesthetic appeal of the solid. The coating may also have both a protective and decorative function. Examples of protective coatings include stain protectors, laminates, corrosion inhibitors and water-proofing agents. Examples of decorative coatings include paint and wallpaper. As the acylated saccharides are generally environmentally friendly and non-toxic, the materials of the invention may be used on solids in which a coating layer has been applied, without any significant detrimental effects being experienced by the coating. In a preferred embodiment, the substance includes a hydrocarbon. Hydrocarbons are compounds that contain hydrogen and carbon atoms only. They are generally the products or by-products of petroleum manufacture and include products such as solvents, oil or grease. Where the medium is a solid such as a machinery part and the like, the material of the invention may be used as an effective degreaser, thereby removing hydrocarbons such as grease or oil from the solid.

The substance may also be any substance that produces a stain. Substances that produce a stain include for example, food products such as tomato, beetroot, butter, wine and coffee, body fluids such as blood and perspiration, cosmetics such as lipstick and foundation, dirt, grass, dyes and ink, oil and the like. Such substances may include an oily component or a coloured component, which produces the undesirable stain.

The substance may also include an ionic species. Ionic species generally carry a positive or negative charge. Preferably, the ionic species is an anion or cation. Anions or cations are generally derived from inorganic compounds and elements, such as minerals. The ionic species may be any anion or cation. Preferably, the ionic species is selected from the group consisting of chloride, fluoride, sulphate, bromide, calcium, magnesium, potassium, sodium, strontium, boron and mixtures thereof. The substance may include one ionic species or it may include a mixture of ionic species. In a preferred embodiment, the medium is a liquid and one or more ionic species is dissolved or suspended in the liquid. More preferably, the liquid is water. The desalination of water may be desirable to remove high concentrations of ionic species in the form of salts, which may assist to purify the water and furthermore may assist in removing substances that can affect the taste of the water or cause undesirable scale build-up to occur on surfaces.

One or more substances may be removed from medium. When there is more than one substance, the substances may be of one type, or they may be of a mixture of different types. The removal of a substance from a medium may also concomitantly result in the removal or reduction of any odours associated with the substance. For example, the undesirable smell associated with rubber may be reduced by removing the compounds that contribute to the smell of the rubber. The materials of the invention may encapsulate or sequester the substances, thereby allowing for their removal from the medium.

The material of the invention may be introduced to the medium in any manner that allows the material to contact the medium. The material of the invention may be used either in neat form or diluted in a solvent to a desired concentration prior to use.

Suitable methods for introducing the material would be readily apparent to the person skilled in the art. Such methods include for example, direct addition to the medium by wiping, spray application, painting or dipping. The material of the invention may be used to wash the medium from which the substances are desired to be removed. Washing may involve the application of the surface active material to the medium, or it may involve the immersion of the medium in a solution that includes the material of the invention.

When the surface active material is used to protect remove a substance from a medium, the surface active material may be used at any concentration that will enable it to achieve the advantages of the invention. The concentration of surface active material that is used in this application is preferably from about 0.005% to about 3% by weight, more preferably from about 0.1% to about 0.5% by weight, even more preferably from about 0.13% to about 0.25% by weight.

The ability to the material of the invention to remove a variety of substances from a range of different mediums without the use of harsh and potentially toxic or carcinogenic agents may improve the efficiency and reduce the cost associated with many processes. The use of the surface active material of the invention may also allow for more environmentally friendly practices to be adopted.

In a further aspect, the present invention provides a method of compatibilising two or more substances including the addition of a surface active material including an acylated saccharides to the substances. The material of the invention may be used where improved compatibility between two or more substances is desired. Increased compatibility between substances may be desired in some applications where the substances possess desirable attributes, yet are not able to co-exist with one another in a composition or formulation due to the substances exhibiting poor compatibility with each other. Poor compatibility is usually due to a difference in chemical or physical properties. Properties that may affect compatibility include solubility, viscosity, density, hydrophilicity, hydrophobicity, charge density and the like. Preferably, the method compatibilises a hydrophilic and a hydrophobic substance. The material of the invention may be added to the two or more substances to emulsify the substances. In this regard, the substances may be dissolved or suspended in an appropriate medium, such as solid or liquid medium, or mixtures thereof. The substances may also be pure substances that have not been mixed or diluted with a medium. Such substances include for example, oil and water. The ability to compatibilise two or more substances is useful in many industrial processes.

The surface active material of the invention may also act as a wetting agent in order to improve the compatibility of a substrate, such as a solid surface, with various substances. In such applications, the surface active material may be prepared in a solution that is then applied to the substrate as a coating or film. The presence of the surface active material on the substrate may therefore assist to improve the compatibility of the substrate with substances such as liquids or coating compositions. The ability of the surface active material to act as a wetting agent may help to adhere or disperse compounds or compositions on the substrate. In the case of coating compositions, this may allow for more even application of the composition on the substrate.

When the surface active material is used to compatibilise two or more substances, the surface active material may be applied at any concentration that will enable it to achieve the advantages of the invention. The concentration of surface active agent that is used in this method of the invention is preferably from about 0.005% to about 3% by weight, more preferably from about 0.1% to about 2% by weight, even more preferably from about 0.25% to about 0.5% by weight.

The invention further relates to a method of increasing the optical brightness of a fabric, including applying a material including an acylated saccharide to the fabric. The improvement in optical brightness of a fabric may be due to ability of the surface active material of the invention to impart a glossy appearance to the fabric. The glossy appearance may result from the surface active material forming a coating on the fabric. The coating may also be a protective coating that may also impart advantages such as stain resistance. As a result, fabrics that are treated with the surface active material may require less washing with conventional cleaning detergents and agents, thereby allowing the fabric to maintain its colour and appearance for a longer period of time. The method of the invention may be used to increase the optical brightness of any fabric as well as articles that include a fabric. Suitable articles include for example clothing, sheets, towels, furniture coverings, curtains, rugs and carpets.

When the surface active material is used to improve the optical brightness of a fabric, the surface active material may be applied at any concentration that will enable it to achieve the advantages of the invention. The concentration of surface active agent that is used in this method of the invention is preferably from about 0.005% to about 3% by weight, more preferably from about 0.5% to about 1% by weight. It is preferred that the acylated saccharide included in the material used in this application includes short chain fatty acids, such as Ce-Ci₄ fatty acids.

In each of the methods of the present invention, the surface active material may be used in any concentration that will provide the desirable effect. It is desirable that the amount of surface active agent is sufficient to exert a surfactant or surface active effect. As a result, it is preferable that the concentration of surface active material used in the methods of the invention be at or close to the critical micelle concentration (CMC). It would be appreciated by the person skilled in the art that the CMC will vary, depending on the characteristics and components of acylated saccharides that are used in the surface active material of the invention. The skilled addressee will be able to readily ascertain the CMC for a given acylated saccharide and a given surface active material using standard techniques.

In a preferred embodiment, the surface active material is used in the methods of the invention in concentrations of from about 0.05% to about 3% by weight, more preferably from about 0.1% to about 0.5% by weight, even more preferably from about 0.1% to about 0.25% by weight. It would be appreciated by the skilled addressee that the amount of surface active material used for a given application will depend on the nature of the acylated saccharide, the specific application and the desired result. The skilled addressee would be able to ascertain the amount of surface active material required to produce the desired result for a given application.

The surface active materials may be used in neat form in any of the methods of the present invention. For example, an amount of the surface active agent may be applied directly to a surface to order to provide beneficial effects. Alternatively, the surface active material may be diluted in a solvent or formulated in a composition prior to use. The solution or composition may then be used in the methods of the invention.

In each of the methods described above, the surface active material of the invention may be used alone or in combination with a further active agent. The further active agent may interact with the acylated saccharide of the surface active material in order to further improve the benefits provided by the material of the invention through an additive or synergistic effect.

The present invention also relates to compositions including a surface active material including an acylated saccharide. Preferably, the composition is selected from the group consisting of a coating composition, a cleaning composition, a compatibilising composition and a brightening composition.

In one preferred aspect, the composition is a coating composition. It is preferred that the composition is a corrosion inhibitor or a fabric protector.

In another preferred aspect, the composition is a cleaning composition. In one preferred embodiment, the cleaning composition is a detergent, for example, a carpet shampoo, a stain remover or a degreaser. In another preferred embodiment, the cleaning composition is a treatment composition. Treatment compositions may be used to treat the products generated from the industrial process, such as waste water, sludge or oil. The treatment composition may also be used to purify substances, such as water, to render the substance fit for consumption or use in a particular application.

In another preferred aspect, the composition is a compatibilising composition. The compatibilising composition may be an emulsifier or a wetting agent.

The compositions of the present invention may be formulated with appropriate carriers, adjuvants or diluents. Carriers, adjuvants or diluents may include solvents, waxes, excipients, preservatives, stabilisers buffers, propellants, fragrances and the like. Such substances usually do not interact with the surface active material, but may be added to improve the physical or aesthetic properties of the composition. The compositions of the invention may also include a further active agent if desired. Suitable active agents include for example, other surfactant compounds, enzymes, chelating agents and bleaches. The presence of a further active agent in combination with the surface active material may provide an additive or synergistic improvement in beneficial effects when the composition is used. The surface active material of the invention may be included in the compositions at any concentration that will provide a desirable effect. The concentration of material will usually depend on the acylated saccharides and the method of application. The desired concentration for any given composition and application may be ascertained by the person skilled in the art. In a preferred embodiment, the concentration of surface active material including an acylated saccharide in the compositions of the invention is in the range of between about 0.01% to 10% by weight, more preferably, about 1% to 5% by weight, even more preferably about 2% to 4% by weight of the composition.

An aliquot of the composition including the surface active agent may then be taken and used directly in a specific application. Alternatively, the composition may be further diluted with a solvent or other diluent prior to use. The compositions of the invention may be formulated using techniques known in the art. The compositions may be formulated as a solid or a liquid formulation. Suitable solid formulations include for example, powders, granules, pellets, blocks and sticks. Suitable liquid formulations include solutions and sprays. The liquid composition may also be an aerosol that is formulated with an appropriate propellant. Once formulated, the compositions of the invention may be used in neat form or be mixed with a solvent or other diluent or excipient prior to use. The surface active materials and compositions of the invention may also be impregnated into a sponge or cloth, such as disposable cloth, for use.

EXAMPLES

The present invention is described with reference to the following examples. It is to be understood that the examples are illustrative of and not limiting to the invention described herein.

EXAMPLE 1 - Procedure for Formation of Acylated Saccharide of the Invention

In a 1000 ml reaction vessel 202 ml of tert. Butyl alcohol was added to a mixture is of palm oil (380 ml), sodium acetate tri-hydrate (85g), a polysaccharide containing material (24g) and a lipase (72g). The material was then heated at between 35-44°C and agitated for a period of 11 hours followed by filtration to produce the crude product.

EXAMPLE 2 — Further Materials Produced Following the general procedure outlined in Example 1 but using different saccharides as starting materials a number of materials were produced and the results obtained shown in Table 3. TABLE 3

EXAMPLE 3 — Characterisation of Acylated Saccharides

Two of the acylated saccharides produced using the procedures described above were subjected to analysis by gas chromatography to determine the free fatty acid profile of the materials. The two materials chosen were one produced using (1) Chitosan as the saccharide and Palm Kernel Oil as the acyl source, and a second produced using (2) Chitosan as the saccharide and a 1 :1 mixture of Palm Kernel oil (PKO) and Rice Bran Oil (RBO) as the acyl source. The free fatty acid analysis is as shown in Table 4. TABLE 4

PKO - Palm kernel oil RBO - Rice Bran Oil

EXAMPLE 4 - Determination of Critical Micelle Concentration

CRITICAL MICELLE CONCENTRATION (CMC) FOR 2% CONCENTRATION INSTRUMENT / EQUIPMENT : KRUSS K12 Surface Tensiometer

Measurement Temperature : 25°C

2% concentration of surface active agent Table 5 Results:

Cone. X 0.5x 0.25x 0.125x 0.0625X 0.03125X 0.015625X 0

Surface 28.84 31.41 34.15 38.36 44.85 50.74 60.18 71.54 Tension

The CMC as detailed in this example was conducted on a KRUSS K12 surface Tensiometer using the standard technique utilised for this apparatus. The results are shown in figure 2.

EXAMPLE 5 — Carpet Cleaner

A number of different concentrations of the surface active agent of Example 1 was tested in order to assess the ability of the surface active agents to remove soil from carpet and act as a stain remover.

The surface active agent of example 1 was blended with potable water to produce solutions having the surface active material at concentrations of 2%, 4% and 8% by weight.

At a concentration of 2% it was found that the solution could be used as a carpet extraction shampoo and had general carpet cleaning properties. The exact amount of surfactant depended on the soil present on the carpet but was typically found that 30 to 210 ml of 2% surface active per 3.78 litres (US gallon) is suitable for this purpose.

At a concentration of 8%, the surface active agent was observed to be an effective stain remover. The 8% solution in water was applied to the stain, allowed to sit on the stain for a suitable period and then removed with water.

EXAMPLE 6— Carpet Protector

A composition containing the surface active agent may also be used a carpet protector. The composition containing the surface active agent of Example

1 was applied to a carpet in a side by side with a commercially available carpet protector manufactured by Du Pont. The performance of the surface active agent of the present invention was compared with the carpet protection qualities of the control material. It was found that both substances exhibited comparable carpet protection qualities. The composition therefore provided protective effects to the carpet against staining.

EXAMPLE 7— Fabric Brightener

Short to medium chain fatty acids in the acylated saccharide surface active material may also act as an encapsulate. When applied to fabrics, the surface active agent of Example 1 acted as an optical brightener to brighten the appearance of the fabric. For these applications a dosage of about 120-360 ml of a 2% solution containing the surface active material is added to 3.78L (US Gallon) of water.

When applied to a coloured carpet, a brighter, glossy appearance was imparted to the carpet

EXAMPLE 8— Odour Removal

A rubber sheet is washed in a solution containing about 0.13% to 0.5% surface active material, which is prepared by dilution of a 2% composition of the surface active material produced in example 1. To this was added a Rose fragrance to impart a pleasing aroma to the treated material. After washing, the rubber sheet is then dried.

The surface active material effectively removed the substances that contributed the aroma or smell of the rubber.

The same formulation is added to a rubber textile and cotton fabric formulation to act as an emulsifier between the rubber textile and the cotton fabric, and as well as rubber aroma displacement. A pearlescence effect, i.e. a shine or glossy appearance was created when a surface active material of Example 1 was employed. EXAMPLE 9— Water Desalination

The surface active agents may also be used for the desalination of water. In this experiment, sea water from Port Kiang, Malaysia was treated with various concentrations of the surface active material of Example 1.

Calculation of Required Dosage of Surface Active Material:

(a) Volume of Sea water:

Pumping Rate: 100 US gall/minute of sea water per minute Pumping Volume per hour 100 x 60 = 6000 gallons per hour Pumping Volume per day: 6000 x 24 = 144,000 gallons per day

Pumping Volume per month: 144,000 x 30 = 4,320,000 gallons per month

(b) Required Dosage of Surface Active Material at a concentration of 0.5%: Dosage: 4,320,000 gall x 0.005 = 21 ,600 gall or 81 ,648 L per month

The following would be the procedure to mix the surface active material with water containing salts:

1. Take one litre of surface active material.

2. Add 5 litres of Reverse Osmosis water, and mix well. 3. Take one litre or gallon of sea water.

4. Analyse the salts that are present in the sea water.

5. Add the required amount of surface active agent for one litre or 1/2 oz per gallon sea water to achieve a final concentration of surface active in the sea water of 0.025%, 0.05%, 0.4% and 0.8% 6. Mix well for two minutes, then take samples for analysis.

7. Repeat the above for at least four times to confirm.

8. Results detailed in Table 6. TABLE 6. Treatment of Sea Water with Various Concentrations of Surface Active Agent - 0.4%, 0.8%, 0.05% and 0.025%

O

As seen in Table 6, the surface active agent is able to function as an effective desalination agent, and the addition of the surface active agent to the sea water was able to reduce the quantity of various salts in sea water by 78% - 80%.

EXAMPLE 10— Sludge Treatment

The surface active material of the invention may be used as a de-emulsifier. A medium that consists of a mixture of component substances may be treated with the surface active agents in order to separate - out the substances from one another.

Sludge Treatment System

The surface active material may also be used to treat sludge. Sludge is an intermediate product that is generally located in between the oil and water phases in crude oil products. Sludge can be classified as two distinct types. One type is solid sludge. This type of sludge is predominantly tank bottoms from SCOT receiving tanks. This sludge generally comprises sands, clays, corrosion products. The contaminated soil, sand etc may also be included in the solid sludge.

Another type of sludge is liquid sludge. This sludge type is a product of the terminal process and comprises thick slop oil with a high percentage of suspended solids (mainly iron sulphide naphthanate and fine clays). The sludge generally has a high water content that is tightly emulsified with oil.

Sludge residue when removed from the SCOT system is held pending treatment in eight covered concrete bays, each of approximate capacity 300m³. Sludge is deposited into the bays using vacuum trucks.

Sludge generally contains 4 phases: oil, water, solids and an intermediate layer. The intermediate layer floats in between oil and water phase. In order to reduce the amount of intermediate layer that is generated, it is usually necessary to change the density of the intermediate layer by using a surfactant that changes the hydrocarbon structure of the layer. To enable treatment of the intermediate layer, the four phases of sludge are separated so that the intermediate layer can be taken out. Alternatively, a chemical which can disperse the components of the intermediate layer into either the water phase or the oil phase may be used. It is desirable to treat the intermediate layer, as its presence reduces the efficiency of the treatment of sludge as the density of the intermediate layer is in between that of the oil and water.

HEAVY SLUDGE TRIAL TESTING

Four test samples of heavy sludge were tested at temperatures of 35, 50 and 7O⁰C. A surface active material was prepared using 60% crude palm oil and

40% palm kernel oil. This material is produced using the process which is the same as in Example 1 with both palm oil and palm kernel oil being separately used to produce two separate surface active materials. These are then blended in a ratio of 60% to 40% to produce the desired combination of surface active materials.

Test A. Procedure:

^■ Dispense 10 ml of heavy sludge into a beaker. It is assumed that the sludge contains 60% hydrocarbon content i.e. the heavy sludge contains 6ml of hydrocarbon;

■ Heat the sample to 35°C.

^■ Add 0.03ml of surface active agent to the sludge. This amount of surface active material provides a final concentration of surface active of 0.5% relative to the hydrocarbon content in the sludge. ^■ Stir well, and centrifuge at 4000 rpm for 10 minutes

The quantity of each component of the sludge that is isolated after treatment of the heavy sludge with the surface active material is shown in Table 7. Table 7. Quantity of components isolated from heavy sludge treated at 35°C

Test B.

■ Same procedure as Test A, except heat the sample to 50⁰C.

The quantity of each component of the sludge that is isolated after treatment of the heavy sludge with the surface active material is shown in Table 8.

Table 8. Quantity of components isolated from heavy sludge treated at 50⁰C

Test C.

Same procedure as Test A, except heat the sample to 70⁰C.

The quantity of each component of the sludge that is isolated after treatment of the heavy sludge with the surface active material is shown in Table 9. Table 9. Quantity of components isolated from heavy sludge treated at 70⁰C

The results obtained show that the surface active material is able to effectively treat heavy sludge and separate the components of the heavy sludge into four fractions at a range of treatment temperatures.

EXAMPLE 11 - Total Petroleum Hydrocarbon Content

The surface active material may be used to reduce the total petroleum hydrocarbon (TPH) content in solids isolated from sludge.

The solid from the sludge samples of Example 10 that had been treated with a surface active material was isolated after the oil, sludge and water was decanted from the solid. The TPH content in the solid isolated from the treated sludge samples was then compared with a control sample of solid isolated from sludge that had no pre-treatment. These results are shown in Table 10.

Table 10. Comparison of TPH for treated and untreated solid

No treatment

Total Petroleum Hydrocarbon (TPH) content of the solid in the treated material had a TPH of 7.8% compared with the control sample, which had a TPH content of 14.8%. As a result, the treated solid showed a reduction of TPH by

47.3% relative to the control sample.

The TPH of solids from treated sludge was also assessed at various stages of separation of the crude fractions of the heavy sludge. These stages are the

Decanter stage, in which the solid and liquid phases are separated, and Tricanter stage, in which all the liquid phases (oil, sludge and water) are separated. The results are shown in Table 11.

Table 11. Comparison of TPH in solids at various stages of heavy sludge separation

* No treatment

EXAMPLE 12 — Sludge Treatment in Tank The surface active material of example 1 may be used to treat sludge in a tank.

A sample of sludge was treated by adding the surface active material to achieve a 0.5% concentration of surface active (relative to the hydrocarbon content of the sludge) in the holding tank prior to the Decanter stage, followed by the addition of amount of surface active to provide a further 0.5% of the surface active material in the holding tank prior to the Tricanter stage.

Following the experimental procedure of Example 9, the surface active is dosed after the heavy sludge is heated to 35°C and stirred well. After centrifuging at 4000 rpm for 10 minutes, various components of the sludge were extracted at the following rates: Oil - 42%, Heavy Sludge — 41%, Water —10% and Solids —

7%.

For comparison, a control sludge sample that was not treated with a surface active material was heated to 35°C then centrifuged at 4000 rpm for about 10 minutes. The recovery of crude oil from the sludge is 2% Heavy Sludge — 78%, Water - 15%, Solids — 5%.

Various characteristics of the fractions isolated at the Decanter and Tricanter stages of the separation during the treatment of heavy sludge were determined and compared. These results are shown in Table 12.

Table 12. Comparison of various characteristics in fractions of heavy sludge isolated at different stages of separation

No treatment

The addition of surface active by injection every 24 hours at a dosage of

0.5%, if the heavy sludge is held in the holding tank for 24 hours, results in the recovery of oil from the sludge between 44% to 47%. The surface active treated sample provides an increase in recovery of oil by

40% and reduction in the recovery of heavy sludge by 37%.

The total petroleum hydrocarbon (TPH) in the solids leaving the Decanter of sludge treated with the surface active material is low enough to be directed the ESP Bio remediation Plant.

Trials on various types of sludge samples i.e. thin or thick sludge, which is known as SLOP and SLUDGE respectively, shows that the content of Total Petroleum Hydrocarbon (TPH) in solids can be decreased to below 10%.

Waxy material (containing mostly hydrocarbon fractions C₂₈-C₃₅) present in an untreated sample of control heavy sludge is above 80%. This is compared to the treated heavy sludge, which contains less than 70% of hydrocarbon fractions

C18-C24.

Water separated from SLOP and SLUDGE treatments normally start with a water COD (Chemical Oxygen Demand) in excess of 100 ppm and needs to be treated to provide a COD below 16 ppm prior to discharge. When used to treat water, the surface active material is able to reduce the COD to a level of around 32 ppm, and thus it requires less effort to then bring the COD level down to the required level of 16 ppm.

The usual processes of heating, decanting and tricanting for the treatment of SLUDGE usually provide a TPH content of the solids at a level of about 35 to 38%. These solids are then treated using an enzymatic process in order to bring the TPH content to below 10% before it may be disposed of. The enzymatic treatment process takes some 21 to 28 days to complete. Using the surface active agent, the TPH may be reduced to a level below 3 to 4%. At these low levels, it may be possible to dispose the solids immediately without further treatment.

In treating heavy sludge, a surface active material including an acylated saccharide including a blend of (50:50) Crude Palm Oil and Palm Kernel Oil provides better de-emulsification results than a surface active material that includes an acylated saccharide prepared using either one of the palm base surfactants alone. Blends of the surfactant materials are produced by producing the individual surfactant materials using the general procedure outlined in example 1 as a first step. This is followed by blending the desired amounts of the individual surfactants to produce the desired blend in the desired ratio. For example to produce a 50:50 blend of Crude Palm Oil and Palm Kernel Oil surfactant equal amounts of surface active material produced using these two glyceride sources are blended to produce the final material.

EXAMPLE 13 - Use of Different Surface Active Material for Sludge Treatment Different surface active materials were assessed for sludge treatment at different treatment temperatures. The surface active materials included blends of acylated saccharide derived from crude palm oil and palm kernel oil at blend ratios of 60:40 and 50:50.

Test A.

The procedure for the investigation is as follows:

• Dispense 10 ml of heavy sludge sample into a beaker. It is assumed that the sludge had a hydrocarbon content of 60% (i.e. 60 % of 10ml is 6 ml of hydrocarbon); • Heat the sample to 35⁰C

• Add the different surface active materials to the heavy sludge to provide final concentrations of 0.5% and 1.5% of the 60:40 and the 50:50 blended surface active material in the sludge, relative to the hydrocarbon content (e.g. add 0.03 ml and 0.09 ml of the 60:40 and the 50:50 blends respectively, to the sludge sample)

• Stir well, and centrifuge at 4000 rpm for 10 minutes

The quantity of each component of the sludge that is isolated after treatment of the heavy sludge with the surface active material is shown in Table 13. Table 13. Quantity of components isolated from heavy sludge treated at 35⁰C with surface active material containing either a 60:40 or 50:50 blend of crude palm oil and palm kernel oil

Test B.

• Same procedure as Test A, except heat the sample to 5O⁰C.

The quantity of each component of the sludge that is isolated after treatment of the heavy sludge with the surface active material is shown in Table 14.

Table 14. Quantity of components isolated from heavy sludge treated at 50⁰C with surface active material containing either a 60:40 or 50:50 blend of crude palm oil and palm kernel oil

Test C.

• Same procedure as Test A, except heat the sample to 70⁰C.

The quantity of each component of the sludge that is isolated after treatment of the heavy sludge with the surface active material is shown in Table 15. Table 15. Quantity of components isolated from heavy sludge treated at 70⁰C with surface active material containing either a 60:40 or 50:50 blend of crude palm oil and palm kernel oil

The above experiments show that the 60:40 and the 50:50 blends derived from crude palm oil and palm kernel oil provide similar results at each treatment temperature.

The oil obtained after the each treatment of Tests A₁ B and C above was then decanted from the mixture and the remaining material, which is composed of the solids, a heavy sludge fraction and water is further treated with an additional quantity of the surface active materials.

The procedure for the investigation is as follows:

Decanter the oil from Test A.

The amount of material (heavy sludge, solids and water) remaining was 6.8 ml (for 60:40 blend) and 6.9 ml (for the 50:50 blend). It is assumed that the hydrocarbon content of the remaining material is 60%. As a result, the remaining material contains 4.08 ml and 4.14 ml hydrocarbon, respectively;

Heat the sample 35⁰C

Add the different surface active materials to the heavy sludge to provide final concentrations of 0.5% and 1.5% of the surface active material in the sludge, relative to the hydrocarbon content (e.g. add 0.02 ml and 0.06 ml of the 60:40 and the 50:50 blends respectively, to the sludge sample)

Stir well, and centrifuge at 4000 rpm for 10 minutes. The quantity of each component of the sludge that is isolated after treatment of the heavy sludge with the surface active material is shown in Table 16.

Table 16. Quantity of components isolated from heavy sludge treated at 35⁰C with surface active material containing either a 60:40 or 50:50 blend of crude palm oil and palm kernel oil

Test B₁.

• As for Test A₁ , except heat the sample to 50⁰C

The quantity of each component of the sludge that is isolated after treatment of the heavy sludge with the surface active material is shown in Table 17.

Table 17. Quantity of components isolated from heavy sludge treated at 50⁰C with surface active material containing either a 60:40 or 50:50 blend of crude palm oil and palm kernel oil

Test C₁.

• As for Test Ai , except heat the sample to 70⁰C

The quantity of each component of the sludge that is isolated after treatment of the heavy sludge with the surface active material is shown in Table 18. Table 18. Quantity of components isolated from heavy sludge treated at 70⁰C with surface active material containing either a 60:40 or 50:50 blend of crude palm oil and palm kernel oil

After the first treatment of the heavy sludge with the 60:40 and 50:50 blends of surface active materials at 35°C, 50⁰C and 70⁰C in Tests A, B and C, approximately 35% oil and 38% sludge material was recovered from the heavy sludge. After removal of the oil and further treatment of the remaining material at

35⁰C, 50°C and 70°C as shown in Tests A₁, B₁ and d, a further 5% to 8 % oil was able to be recovered.

As a result, it was possible to recover about 44% oil in total from the heavy sludge, and furthermore reduce the overall quantity of residual sludge to about 30%.

EXAMPLE 14 — Oil / Water Emulsification

An investigation was performed to determine whether the surface active material can be used as an effective emulsifying agent, to compatibilise crude oil and water.

A control crude oil treatment sample was prepared as follows:

1. Take 50 ml of crude oil.

2. Add 50 ml of toluene.

3. Add 3 drops of F-46 4. Centrifuge for 10 minutes at 4,500 rpm. 5. The results obtained were multiplied by 2 to bring it to 100ml.

A crude oil sample treated with the surface active material was prepared as follows:

1. Take 50 ml of crude oil. 2. Add 0.15 ml of surface active material produced in example 1.

3. Centrifuge for 10 minutes at 4,500 rpm.

4. The results obtained were multiplied by 2 to bring it to 100 ml.

The results of amounts of the various fractions of oil, water and sludge isolated after treatment of crude oil with the surface active material is shown in Table 19.

Table 19. Comparison of the amount of various fractions obtained from control crude oil sample and crude oil treated with surface active agent

The surface active agent promoted and enhanced crude oil and water interfaces and produced good interaction between the immiscible oil and water phases, thereby resulting in increased quantities of the intermediate sludge layer.

EXAMPLE 15 -Water Purification

A water purification trial was conducted at the Caltex Terminal at Duri, Sumatra, Indonesia.

Water contaminated with crude oil samples were treated with a surface active material including an acylated saccharide including a blend of (50:50) or (60:40) Crude Palm Oil and Palm Kernel Oil in an amount of 0.13%, relative to the quantity of crude oil. It is necessary to treat the water to improve the quality of the water before it can be discharged into various stages of a plant, such as an oil refinery. For discharge into the environment, the allowable quantity of oil in the discharge water is 25 ppm.

The water generally forms an emulsion with the crude oil contaminant. The surface active material is investigated for use as a de-emulsifier to separate the oil from the water prior to discharge of the water.

The quantity of crude oil as a contaminant in water was determined for samples that had been treated with the surface active material, and also for control water samples that received no treatment. This experiment was performed for different water discharge stages in the plant. A comparison of the results obtained for the different water samples, together with the maximum allowable quantity of crude oil contaminant at the various stages of water discharge are shown in Table 20.

Table 20. Quantity of crude oil contaminant in water samples with and without treatment with surface active material

EXAMPLE 16 — Detergent and Degreaser Formulation

DETERGENT

In the preparation of the detergent, 100 g of the surface active material is dissolved in 5 litres of water. This is then filtered to provide a liquid detergent product having a concentration of 2% of the surface active material prepared in example 1.

The detergent is formulated into a spray composition for the cleaning and pre-treatment of floors. The composition can be used for the treatment of all types of floors, including synthetic floors.

The cleaning ability of the composition is enhanced by the presence of enzymes (typically lipases) in the composition, which create enzymatic reactions, to release dirt and oil from the floor, thereby making it easier to remove and extract the dirt. The detergent composition left no residual detergent after application, is biodegradable and eliminated microbial growth.

DEGREASER

The detergent composition prepared above was also tested for its ability to act as a degreaser to remove light and heavy greasy soils. The test involved spraying a composition containing the surfactant onto a grease stain followed by wiping the sprayed area with a clean cloth. The grease stain was typically removed following this procedure.

The surface active material also emulsifies and suspends oil and dirt for easy removal during steam cleaning and cold extraction.

The surface active also removed foul odours from mould, mildew and bacteria associated with the greased and soiled surfaces.

The surface active kills micro-organisms, disinfects sanitisers and deodorises.

EXAMPLE 17— Corrosion Inhibitor

A surface active material containing a blend of (60:40) crude palm oil and palm kernel oil is formulated into a coating composition. When the coating composition is applied to a surface, a protective coating is formed on the surface. The composition provides an impermeable coating to stop the oxidizing chemical reaction from occurring. The composition is able to remove an amount of salt from the medium.

The coating composition provides resistance to oxidation which is a critical property for all machines, but especially more critical for machines that requiring extended life at elevated temperatures, such as turbines, aircraft engines, and hydraulic systems.

Finally, it is to be understood that various alterations, modifications and/or additions may be introduced into the constructions and arrangements of parts previously described without departing from the spirit or ambit of the invention.

Claims

CLAIMS:

1. Use of a surface active material including an acylated saccharide as a surfactant.

2. Use according to claim 1 wherein the acylated saccharide is an acylated polysaccharide.

3. Use according to claim 2 wherein the polysaccharide is chitosan.

4. Use according to claim 3 wherein the chitosan is N-acylated.

5. Use according to any one of claims 1 to 4 wherein the material includes more than one acylated saccharide.

6. Use according to any one of claims 1 to 5 wherein the material includes a plurality of acylated saccharides.

7. Use according to claim 5 or 6 wherein each acylated saccharide is an acylated polysaccharide.

8. Use according to claim 7 wherein the polysaccharide is chitosan.

9. Use according to any one of the preceding claims wherein the acylated saccharide(s) include acyl components derived from fatty acids selected from the group consisting of capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, and α-linolenic acid.

10. Use according to any one of the preceding claims wherein the saccharide is polyacylated.

11. Use according to claim 10 wherein the acylated saccharide includes at least one acyl group derived from a Ca-Ci₄ fatty acid and at least one acyl group derived from a Ci₂-Ci₅ fatty acid.

12. Use according to any one of the preceding claims wherein the acyl component of the material has the following free fatty acid profile upon GC MS analysis of the material:

Fatty Acid Percentage of Acyl Component

C6:0 0.0 to 0.3%

C8:0 0.0 to 5.0%

C10:0 0.0 to 5.0%

C12.O 10.0 to 60%

C14:0 5.0 to 20.0%

C16:0 5.0 to 15.0%

C18:0 0.0 to 4.0%

C18:1 10.0 to 30.0%

C18:2 0.0 to 25.0%

C18:3 0.0 to 1.0%

C20:0 0.0 to 1.0%

C22:0 0.0 to 1.0%.

13. Use according to claim 12 wherein the acyl component of the material has one of the free fatty acid profiles provided in Table 4 upon hydrolysis.

14. A method of protecting a surface, including applying a surface active material including an acylated saccharide to the surface.

15. A method according to claim 14 wherein the material including an acylated saccharide forms a coating on the surface.

16. A method according to claim 14 or claim 15 wherein the surface includes fibres.

17. A method according to claim 16 wherein the surface is a carpet.

18. A method according to claim 14 or claim 15 wherein the surface includes a material selected from the group consisting of wood, metal, plastic, ceramic, concrete, glass, stone and leather.

19. A method according to claim 18 wherein the surface includes a metal.

20. A method according to claim 19 wherein the metal includes an oxidisable metal.

21. A method of removing at least one substance from a medium, including contacting the medium with a surface active material including an acylated saccharide.

22. A method according to claim 21 wherein the medium is a solid, liquid or mixtures thereof.

23. A method according to claim 22 wherein the medium is a liquid and wherein the substance is dispersed in the liquid.

24. A method according to claim 23 wherein the liquid is water.

25. A method according to claim 22 wherein the medium is a solid.

26. A method according to claim 25 wherein the solid includes fibres.

27. A method according to claim 26 wherein the solid is a carpet.

28. A method according to claim 25 wherein the solid includes a material selected from wood, metal, plastic, ceramic, concrete, glass, stone and leather.

29. A method according to claim 28 wherein the solid is a window, bench, wall, ceiling or floor.

30. A method according to any one of claims 25 to 29 wherein the solid includes a coating.

31. A method according to claim 30 wherein the coating is a protective or decorative coating.

32. A method according to claim 21 wherein the substance is an industrial waste product.

33. A method according to any one of claims 21 to 32 wherein the substance is a hydrocarbon.

34. A method according to claim 33 wherein the hydrocarbon is oil or grease.

35. A method according to any one of claims 21 to 31 wherein the substance produces a stain.

36. A method according to any one of claims 21 to 35 wherein the substance includes an ionic species.

37. A method according to claim 36 wherein the substance includes a plurality of ionic species.

38. A method according to claim 36 or claim 37 wherein the ionic species is a cation or anion.

39. A method according to claim 38 wherein the ionic species is selected from the group consisting of chloride, fluoride, sulphate, bromide, calcium, magnesium, potassium, sodium, strontium, boron and mixtures thereof.

40. A method according to claim 21 wherein the medium is an emulsion.

41. A method of compatibilising two or more substances, including adding a surface active material including an acylated saccharide to the substances.

42. A method according to claim 41 wherein the method compatibilises a hydrophilic substance and a hydrophobic substance.

43. A method of increasing the optical brightness of a fabric, including applying a surface active material including an acylated saccharide to the fabric.

44. A method according to any one of claims 14 to 43 wherein the surface active material is present in an amount of from about 0.005% to about 3%.

45. A method according to any one of claims 14 to 44 wherein the surface active material is present in an amount of from about 0.1% to about 0.5%.

46. A method according to any one of claims 14 to 43 wherein the surface active material is present in an amount sufficient to form micelles.

47. A method according to any one of claims 14 to 46 wherein the acylated saccharide is an acylated polysaccharide.

48. A method according to claim 47 wherein the polysaccharide is chitosan.

49. A method according to claim 48 wherein the chitosan is N-acylated.

50. A method according to any one of claims 14 to 49 wherein the material includes more than one acylated saccharide.

51. A method according to any one of claims 14 to 50 wherein the material includes a plurality of acylated saccharides.

52. A method according to claim 50 or 51 wherein each acylated saccharide is an acylated polysaccharide.

53. A method according to claim 52 wherein the polysaccharide is chitosan.

54. A method according to any one of claims 14 to 53 wherein the acylated saccharide(s) include acyl components derived from fatty acids selected from the group consisting of capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, and α-linolenic acid.

55. A method according to any one of claims 14 to 54 wherein the saccharide is polyacylated.

56. A method according to claim 55 wherein the acylated saccharide includes at least one acyl group derived is from a C₈-Ci₄ fatty acid and at least one acyl group derived from a C₁₂-C₁₅ fatty acid.

57. A method according to any one of claims 14 to 56 wherein the acyl component of the material has the following free fatty acid profile upon GC MS analysis of the material: Fatty Acid Percentage of Acyl Component

C6:0 0.0 to 0.3%

C8:0 0.0 to 5.0%

C10:0 0.0 to 5.0%

C12:0 10.0 to 60%

C14:0 5.0 to 20.0%

C16:0 5.0 to 15.0%

C18:0 0.0 to 4.0%

C18:1 10.0 to 30.0%

C18:2 0.0 to 25.0%

C18:3 0.0 to 1.0%

C20:0 0.0 to 1.0%

C22:0 0.0 to 1.0%.

58. A method according to claim 57 wherein the acyl component of the material has one of the free fatty acid profiles provided in Table 4 upon hydrolysis.

59. A composition including a surface active material including an acylated saccharide.

60. A composition according to claim 59 which is a coating composition, a cleaning composition, a compatibilising composition or a brightening composition.

61. A cleaning composition according to claim 60 wherein the composition is a detergent, a stain remover or a degreaser.

62. A cleaning composition according to claim 61 wherein the composition a treatment composition.

63. A cleaning composition according to claim 62 wherein the composition is a de-emulsifier.

64. A coating composition according to claim 60 wherein the composition is a corrosion inhibitor or a fabric protector.

65. A compatibilising composition according to claim 60 wherein the composition is an emulsifier.

66. A compatibilising composition according to claim 60 wherein the composition is a wetting agent.

67. A composition according to any one of claims 59 to 66 wherein the acylated saccharide is an acylated polysaccharide.

68. A composition according to claim 67 wherein the polysaccharide is chitosan.

69. A composition according to claim 65 wherein the chitosan is N-acylated.

70. A composition according to any one of claims 59 to 69 wherein the material includes more than one acylated saccharide.

71. A composition according to any one of claims 59 to 70 wherein the material includes a plurality of acylated saccharides.

72. A composition according to claim 70 or 71 wherein each acylated saccharide is an acylated polysaccharide.

73. A composition according to claim 72 wherein the polysaccharide is chitosan.

74. A composition according to any one of claims 59 to 73 wherein the acylated saccharide(s) include acyl components derived from fatty acids selected from the group consisting of capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, and α-linoleic acid.

75. A composition according to any one of claims 59 to 74 wherein the saccharide is polyacylated.

76. A composition according to claim 75 wherein the acylated saccharide includes at least one acyl group derived from a C₈-Ci₄ fatty acid and at least one acyl group derived from a C₁₂-C₁₅ fatty acid.

77. A composition according to any one of claims 59 to 76 wherein the acyl component of the material has the following free fatty acid profile upon GC MS analysis of the material:

Fatty Acid Percentage of Acyl Component

C6:0 0.0% to 0.3%

C8:0 0.0% to 5.0%

C10:0 0.0% to 5.0%

C12:0 10.0% to 60%

C14:0 5.0% to 20.0%

C16:0 5.0% to 15.0%

C18:0 0.0% to 4.0%

C18:1 10.0% to 30.0%

C18:2 0.0% to 25.0%

C18:3 0.0% to 1.0%

C20:0 0.0% to 1.0%

C22:0 0.0% to 1.0%.

78. A composition according to claim 71 wherein the acyl component of the material has one of the free fatty acid profiles provided in Table 4 upon hydrolysis.

79. A composition according to any one of claims 59 to 78 wherein the surface active material is present in the composition in an amount of between about 0.01% to 10% by weight.

80. A composition according to any one of claims 59 to 79 wherein the surface active material is present in an amount of from about 0.005% to about 3% by weight of the composition.

81. A composition according to any one of claims 59 to 80 wherein the surface active material is present in an amount of from about 0.1% to about 0.5% by weight of the composition.

82. A composition according to any one of claims 59 to 79 wherein the surface active material is present in an amount sufficient to form micelles.