WO2025008628A1

WO2025008628A1 - Compositions and methods and uses related thereto

Info

Publication number: WO2025008628A1
Application number: PCT/GB2024/051732
Authority: WO
Inventors: Peter SWALLOW; Tony Gough; Ian Malcolm Mcrobbie
Original assignee: Innospec Ltd
Current assignee: Innospec Ltd
Priority date: 2023-07-05
Filing date: 2024-07-03
Publication date: 2025-01-09
Anticipated expiration: 2026-01-05
Also published as: GB202409672D0; GB202310301D0; GB2631596A

Abstract

A method of preparing a taurate surfactant composition, the method comprising reacting a carboxylic acid of formula R¹COOH or a reactive equivalent thereof with a compound of formula (I): (I) wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R1 represents an optionally substituted C₃-C₃₅ hydrocarbyl group; each of R², R³, R⁴, R⁵ and R⁶ independently represents hydrogen or a C₁-C₄ alkyl group; wherein the compound of formula (I) has a percentage renewable carbon index (RCI) of at least 50%.

Description

Compositions and methods and uses related thereto

The present invention relates to taurate surfactant compounds, compositions comprising such compounds and methods and uses relating thereto.

Taurate compounds are common, versatile surfactants that can be used in a variety of applications. They are particularly useful in personal care applications due to their low irritancy potential, desirable foaming properties, high solubility and stability.

However current commercial compositions comprising such surfactants are derived from petrochemical sources.

Environmental concerns are becoming increasingly important to consumers with many seeking to purchase household and cosmetic products having a reduced environmental impact.

Therefore it is highly desirable to provide surfactants that can be prepared from renewable carbon sources.

In this specification when we refer to renewable carbon sources we mean to include all carbon sources that are not directly obtained from petrochemicals. However the term is intended to encompass recovered or recycled carbon that may originally have been obtained from such sources.

Thus renewable carbon sources may include those classed as green (plant derived), blue (marine derived), purple (deriving from carbon capture) or grey (from plastics or pyrolysis of other material).

According to the first aspect of the present invention there is provided a method of preparing a taurate surfactant composition, the method comprising reacting a carboxylic acid of formula R¹COOH or a reactive equivalent thereof with a compound of formula (I):

wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R¹ represents an optionally substituted C3-C35 hydrocarbyl group; and each of R², R³, R⁴, R⁵ and R⁶ independently represents hydrogen or a C1-C4 alkyl group; and wherein the compound of formula (I) has a percentage renewable carbon index (RCI) of at least 50%.

The method of the first aspect of the present invention relates to a method of preparing a taurate surfactant composition. The taurate composition provided may consist essentially of one or more taurate compounds or it may comprise one or more further components. The one or more further components may, for example, include by-products, residual starting materials, impurities or solvents.

According to a second aspect of the present invention there is provided a surfactant composition comprising one or more taurate compounds of formula (II):

wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R¹ represents an optionally substituted C3-C35 hydrocarbyl group; and each of R², R³, R⁴, R⁵ and R⁶ independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR⁶CR²R³CR⁴R⁵SC>3X in the compound of formula (II) are from a renewable carbon source.

In some preferred embodiments the surfactant composition of the second aspect may be provided by the method of the first aspect.

According to a third aspect of the present invention there is provided a compound of formula (II):

(II) wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R¹ represents an optionally substituted C3-C35 hydrocarbyl group; and each of R², R³, R⁴ and R⁵ independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR⁶CR²R³CR⁴R⁵SC>3X in the compound of formula (II) are from a renewable carbon source.

In the first, second and third (and further) aspects of the invention R¹ represents an optionally substituted C3-C35 hydrocarbyl group. For the avoidance of doubt the present invention includes embodiments in which mixtures of compounds are present and thus R¹ may represent different hydrocarbyl groups including mixtures of differing carbon chain length within the C3-C35 range.

According to a fourth aspect of the present invention there is provided a compound of formula (I):

wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; and each of R², R³, R⁴, R⁵ and R⁶ independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms in the compound are from a renewable carbon source.

Preferred features of the first, second, third and fourth aspects will now be described.

References herein to the surfactant composition of the present invention unless otherwise stated may refer to the surfactant composition of the second aspect and/or the surfactant composition provided by the first aspect. R¹ represents an optionally substituted C3-C35 hydrocarbyl group, R², R³, R⁴ and R⁵ each independently represents hydrogen or a substituted or unsubstituted C1-C4 alkyl group, provided that at least one of R², R³, R⁴ and R⁵ is not hydrogen, and X represents a cation.

Suitably R¹ represents an optionally substituted C3-C35 alkyl, C3-C35 alkenyl, C6-C12 aryl or Cs- C22 alkyl-Ce-Ci2 aryl group. More suitably, R¹ represents an optionally substituted C3-C35 alkyl or C3-C35 alkenyl group, especially an optionally substituted C3-C35 alkyl group. Most suitably, R¹ represents a C3-C35 alkyl or C3-C35 alkenyl group, especially a C3-C35 alkyl group.

In some embodiments R¹ represents a mixture of optionally substituted C3-C35 alkyl, C3-C35 alkenyl, C6-C12 aryl or C8-C22 alkyl-Ce-Ci2 aryl groups having differing chain lengths.

For example R¹ may be derived from the mixture of fatty acids having differing chain lengths found in triglyceride oils for example coconut oil, palm oil, palm kernel oil or rapeseed oil.

Suitably R¹ represents an optionally substituted C3-C35 alkyl or C3-C35 alkenyl group, such as an optionally substituted Cs-Cis alkyl or Cs-Cis alkenyl group.

Suitably R¹ represents a C3-C35 alkyl or C3-C35 alkenyl group, such as a Cs-Cis alkyl or Cs-Cis alkenyl group.

Suitably R¹ represents an optionally substituted C4-C29 alkyl group, such as an optionally substituted C7-C23 alkyl group, for example an optionally substituted C7-C21 alkyl group, preferably an optionally substituted C7-C17 alkyl group.

Suitably R¹ represents a C4-C29 alkyl group, such as a C7-C23 alkyl group, for example a C7-C21 alkyl group, preferably a C7-C17 alkyl group.

R¹ is suitably provided by one or more fatty acids (i.e. one or more acids of formula R¹COOH). Fatty acids obtained from natural oils often include mixtures of fatty acids. For example, the fatty acid obtained from coconut oil contains a mixture of fatty acids including C12 lauric acid, C14 myristic acid, C palmitic acid, Cs caprylic acid, C10 capric acid and C stearic and oleic acid.

R¹ may be provided by one or more naturally occurring fatty acids and/or of one or more synthetic fatty acids. For example, R¹ may consist essentially of the residue of a single fatty acid.

Most preferably R¹ is provided by one or more naturally occurring and/or renewable fatty acids. Examples of carboxylic acids from which R¹ may be derived include coco acid, hexanoic acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, arachidic acid, gadoleic acid, arachidonic acid, eicosapentanoic acid, behenic acid, erucic acid, docosahexanoic lignoceric acid, naturally occurring fatty acids such as those obtained from coconut oil, tallow, palm kernel oil, butterfat, palm oil, olive oil, corn oil, linseed oil, peanut oil, fish oil and rapeseed oil; synthetic fatty acids made as chains of a single length or a selected distribution of chain lengths; and mixtures thereof. R¹ may also be derived from fatty acids obtained via fermentation or general biotechnological processes, or from waste vegetable oils. These may be obtained by chemical or enzymatic routes.

Suitably R¹ is provided by coco acid, mixed fatty acids derived from coconut oil or the mixed fatty acids derived from palm kernel oil. Suitable coconut derived feedstocks include coconut fatty acid, coconut oil, coconut oil methyl esters, virgin coconut oil, refined bleached and deodorised coconut oil, ‘distilled and topped’ hardened coconut fatty acid and methyl esters thereof. Also useful are palm oil, hydrogenated palm kernel oil derived C12-C18 fatty acids (hardened and topped fatty acid) and methyl esters thereof. In some embodiments, R¹ predominantly comprises the residue of a saturated fatty acid having 12 carbon atoms.

R¹ may be derived from the mixture of fatty acids having differing chain lengths found in triglyceride oils for example coconut oil, palm oil, palm kernel oil or rapeseed oil.

In some embodiments only a single taurate compound of formula (II) may be present in the surfactant composition of the present invention. In some embodiments a mixture of two or more taurate compounds of formula (II) may be present.

Each of R², R³, R⁴, R⁵ and R⁶ is independently selected from hydrogen or a Ci to C4 alkyl group. In embodiments in which any of R², R³, R⁴, R⁵ and R⁶ is a Ci to C4 alkyl group, the alkyl group is suitably n-propyl, ethyl or methyl, such as ethyl or methyl, most preferably methyl.

In some embodiments R⁶ is a Ci to C4 alkyl group, preferably methyl.

In some embodiments R⁶ is hydrogen.

In some embodiments each of R², R³, R⁴, R⁵ and R⁶ is hydrogen and the compound of formula (II) is an acyl taurate surfactant.

In some embodiments R⁶ is a Ci to C4 alkyl group, each of R², R³, R⁴ and R⁵ is hydrogen and the compound of formula (II) is an acyl N-alkyl taurate surfactant. In such embodiments R⁶ is preferably n-propyl, ethyl or methyl. Preferably R⁶ is ethyl or methyl, most preferably methyl. Thus in such embodiments the compound of formula (II) is preferably an acyl N-methyl taurate surfactant.

In some embodiments R⁶ is a Ci to C4 alkyl group and each of R², R³, R⁴ and R⁵ independently represents hydrogen or a C1-C4 alkyl group wherein at least one of R², R³, R⁴ and R⁵ is not hydrogen.

In such embodiments in which at least one of R², R³, R⁴ and R⁵ represents an optionally substituted C1-C4 alkyl group, the alkyl group is suitably n-propyl, ethyl or methyl, such as ethyl or methyl, most preferably methyl.

Preferably one of the groups R², R³, R⁴ and R⁵ represents an optionally substituted C1-C4 alkyl group and the remaining groups represent hydrogen. For example, R² may represent an optionally substituted C1-C4 alkyl group and R³, R⁴ and R⁵ may all represent hydrogen. For example, R⁴ may represent an optionally substituted C1-C4 alkyl group and R², R³ and R⁵ may all represent hydrogen.

Preferably R² represents a C1-C4 alkyl group and R³, R⁴ and R⁵ all represent hydrogen and/or R⁴ represents a C1-C4 alkyl group and R², R³ and R⁵ all represent hydrogen.

Thus a mixture of compounds may be present in which either R² or R⁴ is a Ci to C4 alkyl group and the remainder of R², R³, R⁴ and R⁵ are hydrogen.

Most preferably R² represents a methyl group and R³, R⁴ and R⁵ all represent hydrogen or R⁴ represents a methyl group and R², R³ and R⁵ all represent hydrogen.

In some embodiments R⁶ is hydrogen and either R² or R⁴ is a Ci to C4 alkyl group, preferably methyl, and the remainder of R², R³, R⁴ and R⁵ are hydrogen.

Suitably X represents hydrogen, a metal cation or an optionally substituted ammonium cation, preferably a metal cation. By “optionally substituted ammonium cation”, we mean to refer to an ammonium cation wherein the nitrogen atom may be substituted with from 1 to 4 optionally substituted hydrocarbyl groups. Suitable ammonium cations include those derived from alkyl amines and alkanolamines. Preferred ammonium cations include isopropanolamine, isopropylamine, ethanolamine, diethanolamine, triethanolamine and 2-amino-2-methyl-1 ,3- propanediol (AMPD). Preferred ammonium cations include NH4⁺ and the ammonium cation of triethanolamine. Suitable metal cations include alkali metal cations, for example sodium, lithium and potassium cations, and alkaline earth metal cations, for example calcium and magnesium cations. Suitably, X represents hydrogen, an alkali metal cation or an optionally substituted ammonium cation. Preferably, X represents a potassium or sodium cation. Most preferably, X represents a sodium cation.

The skilled person will appreciate that when X is a divalent metal cation two moles of anion will be present for each mole of cation.

In some embodiments the surfactant composition of the present invention may comprise the reaction product of N-methyl methyl taurine and one or more fatty acids, that is a compound of formula R¹CONR⁶CHR²CHR⁴SC>3X in which one of R² and R⁴ is methyl and the other is hydrogen. Mixtures of these isomers may be present.

The surfactant composition of the present invention may include a mixture of more than one taurate compound of formula (II). For example, an isomeric mixture of acyl N-alkyl alkyl taurate compounds may be present. Such a mixture may include, for example an acyl N-alkyl alkyl taurate compound in which R² represents a C1-C4 alkyl group (suitably methyl) and R³, R⁴ and R⁵ are all hydrogen and an acyl N-alkyl alkyl taurate compound in which R⁴ represents a C1-C4 alkyl group (suitably methyl) and R², R³ and R⁵ are all hydrogen.

In particular, the surfactant composition of the present invention may comprise a mixture of isomers, that is a compound of formula R¹CONR⁶CH2CHR⁴SC>3X in which R⁴ represents a C1- C4 alkyl group (preferably methyl) and a compound of formula R¹CONR⁶CHR²CH2SC>3X in which R² represents a C1-C4 alkyl group (preferably methyl).

Suitably such mixtures comprise at least 90% of compounds in which R² is methyl and R⁴ is hydrogen and at most 10% of compounds in which R² is hydrogen and R⁴ is methyl.

Preferably the surfactant composition provided by the present invention comprises one or more taurate compounds of formula (II) selected from sodium lauroyl taurate, sodium cocoyl taurate, sodium oleoyl taurate, sodium myristoyl taurate, sodium lauroyl methyl taurate, sodium cocoyl methyl taurate, sodium oleoyl methyl taurate, sodium myristoyl methyl taurate, sodium lauroyl N-methyl methyl taurate, sodium cocoyl N-methyl methyl taurate, sodium oleoyl N-methyl methyl taurate and sodium myristoyl N-methyl methyl taurate. Sodium lauroyl taurate, sodium lauroyl methyl taurate and sodium N-methyl methyl taurate are especially preferred.

In the first aspect of the present invention an acid of formula R¹COOH or a reactive equivalent thereof is reacted with a compound of formula (I). The reaction may be carried out by any suitable means. Such means will be well known to the person skilled in the art. Suitable methods include those described in US1982120, US5434276, US5496959, US3232968 and EP3784652.

In the method of the first aspect a carboxylic acid of formula R¹COOH or a reactive equivalent thereof is reacted with a compound of formula (I).

By a reactive equivalent thereof we mean to refer to a compound which reacts in a similar way to a carboxylic acid, for example, an acid chloride or anhydride.

In some embodiments the method of the first aspect involves reaction of an acid chloride of formula R¹COCI or an acid bromide of formula R¹COBr with a compound of formula (I). This is known as the Schotten-Baumann reaction and suitable reactions of this type are described, for example in US1982180.

In some embodiments the method of the first aspect involves a direct amidation reaction between the acid of formula R¹COOH and the compound of formula (I). In some such embodiments the reaction may be carried out in the presence of a catalyst. Suitable catalysts will be known to the person skilled in the art and include acids and bases.

Suitable conditions for carrying out the method of the first aspect will be known to the person skilled in the art.

In some preferred embodiments the acid of formula R¹COOH or a reactive equivalent thereof is directly reacted with a compound of formula (I) without a solvent.

In some embodiments the reaction is carried out in the presence of a solvent. Suitable solvents will be known to the person skilled in the art and include water, alkylene glycols (e.g. ethylene glycol and propylene glycol) and aprotic solvents for example alpha omega bis alkylated polyalkylene glycols (e.g. glymes).

A preferred solvent is water.

The method of the first aspect involves reaction of a compound of formula (I) with an acid of formula R¹COOH or a reactive equivalent thereof.

The compound of formula (I) may be obtained by reacting an isethionic acid compound of formula (III):

with ammonia or a primary amine compound of formula H2NR⁶ to provide the taurine compound of formula (I).

In formula (III) R², R³, R⁴, R⁵ and R⁶ and X are as defined in relation to the first aspect.

The ammonia or primary amine compound of formula H2NR⁶ used to provide the taurine compound of formula (I) may be optionally produced or obtained from renewable feedstocks.

For example, ammonia can be produced by the Haber-Bosch process using hydrogen derived from electrolysis of water using renewable electricity from solar power, wind turbines or hydroelectrically generated, or using electricity generated from nuclear power, or using hydrogen derived from conventional steam methane reforming where the carbon dioxide generated is captured and stored (ie, not released into the atmosphere).

In some embodiments R⁶ is methyl and the primary amine compound is methylamine. This may be produced in a catalytic process by reaction of ammonia and methanol. Ammonia may be obtained as described above and methanol may be sustainable methanol derived from renewable feedstocks or from conventional processes where the carbon dioxide produced is captured and stored. Bio-methanol may be obtained for example by steam reforming of biogas (bio-methane) to bio-synthesis gas which is then heated over specific catalysts to give biomethanol. Bio-methanol may also be obtained from the industrial process of converting wood into wood pulp which forms bio-methanol as a by-product.

Sustainable methanol may also be obtained by reacting carbon dioxide obtained from sources such as direct air capture, point source capture, or other available biogenic sources like pulp mills and bio-waste to power plants, with hydrogen either obtained by electrolysis of water using renewable electricity or from conventional steam methane reforming where the carbon dioxide generated is captured and stored.

Other methods for obtaining sustainable methanol are known to the skilled person. In some embodiments the compound of formula (I) is taurine. Taurine may be obtained from a microbial source. For example in some embodiments taurine may be synthesised by bacterial fermentation. In some embodiments taurine may be synthesised by algae.

The compound of formula (I) has a percentage renewable carbon index (%RCI) of at least 50%.

Preferably the compound of formula (I) has a percentage renewable carbon index (%RCI) of at least 60%, preferably at least 70%, more preferably at least 80%, preferably at least 90%, suitably at least 98%.

Preferably the compound of formula (I) has a percentage renewable carbon index (%RCI) of from 95 to 100%, preferably from 99 to 100%.

The renewable carbon index (RCI) for a component is calculated according to ISO 16128- 1 :2016, wherein the number of carbon atoms derived from renewable carbon sources is divided by the total number of carbon atoms in a component. The total RCI of the composition is a weighted average of the RCI of each carbon-containing surfactant in the composition. The %RCI is obtained by multiplying the RCI by 100.

This means that in preferred embodiments substantially all of the carbon atoms in the compound of formula (I) are from renewable carbon sources.

Preferably in the method of the first aspect the carboxylic acid of formula R¹COOH or reactive equivalent thereof has a percentage renewable carbon index (%RCI) of at least 50%.

Preferably the carboxylic acid of formula R¹COOH or reactive equivalent thereof has a percentage renewable carbon index (%RCI) of at least 60%, preferably at least 70%, more preferably at least 80%, preferably at least 90%, suitably at least 98%.

Preferably the carboxylic acid of formula R¹COOH or reactive equivalent thereof has a percentage renewable carbon index (%RCI) of from 95 to 100%, preferably from 99 to 100%.

In the compound of formula (II) at least 50% of the carbon atoms provided by the moiety NR⁶CR²R³CR⁴R⁵SC>3X in the compound of formula (II) are from a renewable carbon source.

Preferably at least 60% of the carbon atoms provided by the moiety NR⁶CR²R³CR⁴R⁵SC>3X in the compound of formula (II) are from a renewable carbon source, preferably at least 70%, more preferably at least 80%, preferably at least 90%, suitably at least 98%. Preferably from 95 to 100% or 98 to 100% of the carbon atoms provided by the moiety NR⁶CR²R³CR⁴R⁵SC>3X in the compound of formula (II) are from a renewable carbon source.

In preferred embodiments at least 50% of the carbon atoms provided by the moiety R¹ in the compound of formula (II) are from a renewable carbon source.

Preferably at least 60% of the carbon atoms provided by the moiety R¹ in the compound of formula (II) are from a renewable carbon source, preferably at least 70%, more preferably at least 80%, preferably at least 90%, suitably at least 98%.

Preferably from 95 to 100% or 98 to 100% of the carbon atoms provided by the moiety R¹ in the compound of formula (II) are from a renewable carbon source.

Preferably the or each compound of formula (II) provided by the present invention has a percentage renewable carbon index (%RCI) of at least 50%.

Preferably the or each compound of formula (II) has a percentage renewable carbon index (%RCI) of at least 60%, preferably at least 70%, more preferably at least 80%, preferably at least 90%, suitably at least 98%.

Preferably the or each compound of formula (II) has a percentage renewable carbon index (%RCI) of from 95 to 100%, preferably from 99 to 100%.

One way in which the percentage renewable carbon index of a component can be measured is described in Example 1 .

Another suitable method that can be used to measure the RCI for green, blue, or other biogenic sources of carbon is that described in ASTM D6866.

The surfactant compositions of the present invention may be produced using any suitable renewable source of carbon.

Suitable renewable sources of carbon include those known as grey, purple, green or blue sources of carbon. As will be understood by the skilled person purple carbon is developed from carbon dioxide drawn from industrial emissions; green carbon is obtained from plants and other biological sources; blue carbon is derived from marine sources, for example algae; and grey carbon is chemically recovered from waste materials. Examples of suitable sources of grey carbon which may be useful herein include products from the pyrolysis of waste, for example plastic waste, waste cooking oils and used tyres or waste rubber. Examples of waste plastic which may be pyrolysed to provide carbon for use herein include low density polyethylene, high density polyethylene, ultra-high density polyethylene, polypropylene, polystyrene, polyethylene terephthalates (PET), rubber (e.g. from tyres), polyacrylate and polynitrile.

Examples of suitable sources of purple carbon which may be useful herein include materials developed from carbon captured from air (Direct Air Capture) or captured from the flue stacks during the combustion of fossil fuels (Point Source Capture). Point Source Capture may be carried out for example at power stations or steel manufacturing mills. An example is a process developed by Lanzatech which captures flue gases from heavy industry flue stacks and ferments the gases using certain microbes into feedstocks such as ethanol which can be further converted into feedstocks which can be used in the present invention.

Examples of suitable sources of green carbon which may be useful herein include plants which produce oils, sugar, waste biomass such a agricultural waste and forestry waste, composts and digestate materials such as lignocellulose. Various methods can be used to convert these green carbon derivatives into feedstocks that can be used in the present invention. For example, ethanol obtained from fermentation of sugars can be converted into ethylene or propylene which can be converted into ethylene oxide or propylene oxide. A further example is the conversion of lignocellulose (a waste biomass from trees, bushes and grasses) by thermal catalytic processes into bionaptha. This can be processed further (cracked) into alkene feedstocks such as propylene which can be converted into propylene oxide. Ethylene oxide and propylene oxide may be used to make taurine and N-methyl methyl taurine.

Examples of suitable sources of blue carbon which may be useful herein include algae, algae waste and carbon stored in the vegetation and soils of mangroves, salt marshes, and seagrasses. For example, cracking of lipids derived from algae can give alkenes, for example ethylene and propylene which can be converted into ethylene oxide and propylene oxide and used to make taurine and N-methyl methyl taurine.

The surfactant composition of the present invention may be provided by a mixture of carbon sources.

For example, sodium methyl isethionate derived from bio-propylene may be reacted with methylamine or ammonia to produce respectively N-methyl methyl taurine or methyl taurine as compounds of formula (I). The surfactant composition of the present invention may be provided in solid or liquid form.

In some embodiments the surfactant composition is provided as a powder.

In some embodiments the surfactant composition is provided as an aqueous solution. Such an aqueous solution may be clear or opaque.

In embodiments in which the reaction to form the surfactant composition is carried out under aqueous conditions the mixture obtained may be used directly without purification. In other such embodiments the resultant mixture may be spray dried.

As mentioned above the surfactant composition provided by the present invention may comprise one or more further components such as impurities, byproducts or residual staring materials.

Preferably the surfactant composition provided by the present invention (including any impurities, byproducts or residual staring materials) has a percentage renewable carbon index (%RCI) of at least 50%. Preferably the surfactant composition has a percentage renewable carbon index (%RCI) of at least 60%, preferably at least 70%, more preferably at least 80%, preferably at least 90%, suitably at least 98%.

In preferred embodiments the surfactant composition provided by the present invention comprises less than 30 wt% free fatty acids based on the total mass of solids present in the composition, preferably less than 20 wt%, more preferably less than 15 wt%, suitably less than 10 wt%, preferably less than 5 wt%.

In preferred embodiments the surfactant composition provided by the present invention comprises less than 30 wt% sodium chloride based on the total mass of solids present in the composition, preferably less than 20 wt%, more preferably less than 15 wt%, suitably less than 10 wt%, for example less than 5 wt%.

In some preferred embodiments the surfactant composition provided by the present invention comprises less than 1 wt% sodium chloride, preferably less than 0.5 wt%, more preferably less than 0.1 wt%, suitably less than 0.01 wt%, for example less than 0.001 wt%.

The surfactant composition provided by the present invention may find utility in a wide variety of applications.

According to a fifth aspect of the present invention there is provided the use of a surfactant composition comprising one or more taurate compounds of formula (II):

wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R¹ represents an optionally substituted C3-C35 hydrocarbyl group; each of R², R³, R⁴, R⁵ and R⁶ independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR⁶CR²R³CR⁴R⁵SC>3X in the compound of formula (II) are from a renewable carbon source; in toilet care, automatic dishwashing, manual dishwashing, laundry, fabric care, kitchen care, carpet cleaning, air fresheners, vehicle care, polishing products, machine cleaning and maintenance, pesticides, insecticides, fungicides, herbicides, oilfield chemical applications, marine applications, personal care, institutional I industrial cleaning or emulsion polymerisation compositions.

According to a sixth aspect of the present invention there is provided a formulated composition comprising: a surfactant composition comprising one or more taurate compounds of formula (II):

wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R¹ represents an optionally substituted C3-C35 hydrocarbyl group; each of R², R³, R⁴, R⁵ and R⁶ independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR⁶CR²R³CR⁴R⁵SC>3X in the compound of formula (II) are from a renewable carbon source; and one or more further components. Preferred features of the fifth and sixth aspects of the present invention are as defined in relation to the first, second, third and fourth aspects.

The formulated composition of the sixth aspect comprises a surfactant composition and one or more further components.

By “formulated composition” we mean to refer to a chemical composition which contains multiple components which have been mixed together. The formulated composition is suitably prepared to contain specific ingredients and has a particular purpose. For example the formulated composition may be a cleaning composition, a personal care composition, a home care composition, a composition used in oil fields for oil recovery, a composition used for agrochemical applications or a composition used in other industrial applications.

The types of components that are typically present in such formulated composition will be known to the person skilled in the art.

For example laundry, dishwashing and hard surface cleaning compositions typically comprise ingredients such as surfactants, builders, bleaches, bleach activators, redeposition additives, dye transfer inhibitors, enzymes, colorants and fragrances.

Personal care compositions typically comprise ingredients such as surfactants (including anionic, amphoteric, nonionic and cationic surfactants); conditioning agents (including quaternary ammonium compounds, cationic polymers, cationic conditioning polymers, silicones, synthetic or natural oils or resins etc), fatty alcohols, electrolytes or other rheology modifiers, opacifying/pearlising agents, moisturizing agents, anti-dandruff and other scalp benefit agents, fragrances, dyes, UV filters, penetration enhancers (eg, propylene carbonate, benzyl alcohol etc), preservatives, antioxidants and other skin benefit agents, emulsifiers, pH adjusting agents and buffers and styling polymers (eg, polyvinylpyrrolidone etc).

Compositions for use in agrochemical applications may comprise surfactants and components such as herbicides and/or pesticides.

Compositions for use in oil field applications, for example enhanced oil recovery, may comprise surfactants, polymers and alkalising agents.

Compositions for use in other applications such as emulsion polymerisation to prepare polymers or industrial applications may comprise surfactants, monomers and initiators. Preferably the one or more further components are selected from chelating agents, preservatives, pH modifiers, hydrotropes and further surfactants.

The formulated composition may comprise a chelating agent. Suitable chelating agents include ethylenediamine-N,N’-disuccinic acid, methylglycinediacetic acid, glutamic acid N,N-diacetic acid, imino disuccinic acid, diethylene triamine pentaacetic acid, ethylenediamine tetraacetic acid, diethylenetriamine penta methylene phosphonic acid, etidronic acid, phytic acid, polyitaconic acid and anions, salts and mixtures thereof.

Preferred chelating agents are biodegradable chelating agents for example ethylenediamine- N,N’-disuccinic acid, methylglycinediacetic acid, glutamic acid N,N-diacetic acid, imino disuccinic acid and anions and mixtures thereof. Ethylenediamine-N,N’-disuccinic acid (EDDS) is especially preferred. The skilled person will appreciate that polycarboxylic acid chelating agents may be present as the free acid or a salt thereof.

The formulated composition may comprise a preservative. Suitable preservatives will be known to the person skilled in the art and include sodium benzoate, potassium sorbate, sorbic acid, phenoxyethanol, benzyl alcohol, DMDM hydantoin, imidazolidinyl urea, methylchloroisothiazolinone, methylisothiazolinone, salicylic acid, benzyl salicylate, methylparaben, propylparaben and caprylyl glycol. A preferred preservative for use herein is sodium benzoate.

The formulated composition may comprise a hydrotrope. Suitable hydrotropes will be known to the person skilled in the art and include propylene glycol, hexylene glycol, glycerine, sorbitol, xylene sulfonates, cumene sulfonates, ethanol, urea, dipropylene glycol. A preferred hydrotrope for use herein is sorbitol.

The formulated composition may comprise a pH modifier. Suitable pH modifiers will be known to the person skilled in the art and include lactic acid, potassium hydroxide sodium hydroxide, sodium carbonate, triethanolamine and sodium gluconate. A preferred pH modifier is citric acid.

In some embodiments the formulated composition of the present invention is a personal care composition. Preferably such a formulated personal care composition has a pH of from 3 to 9, preferably 4 to 8, for example 4.5 to 7.5.

In some embodiments the formulated personal care composition has a pH of 4.5 to 5.5.

In some embodiments the formulated personal care composition has a pH of 6.5 to 7.5. In some embodiments the formulated composition of the present invention is an agrochemical composition, a home care composition, an oilfield composition or a composition for use in another industrial application. In such embodiments the formulated composition may have a pH of from 2 to 14, preferably 3 to 11 , for example 3.5 to 10.

In some embodiments the formulated composition for use in home care, agrochemical, oilfield or other industrial applications has a pH of 3.5 to 9.

In some embodiments the formulated composition for use in home care, agrochemical, oilfield or other industrial applications has a pH of 4 to 8.

The formulated composition of the invention may comprise one or more further surfactants.

Such surfactants may be selected from anionic surfactants, cationic surfactants, non-ionic surfactants, amphoteric or zwitterionic surfactants, and mixtures thereof. The selection of suitable further surfactants for use in the composition of the present invention is within the competence of the person skilled in the art.

Suitable anionic surfactants for use in formulated composition of the present invention include salts of C12-C18 carboxylic acids, ethoxylated carboxylic acids, ester carboxylates and ethoxylated ester carboxylates and sarcosinates. Other suitable anionic surfactants include sulfates and sulfonates, for example alkyl sulfates, alkyl ether sulfates, alcohol sulfates, alcohol ether sulfates, a-olefin sulfonates, linear alkyl sulfonates; fatty acid methyl ester sulfonates, sulfates of branched alcohols (for example as described in US9493725), phosphate esters and biosurfactants, for example sophorolipids, rhamnolipids, saponins and surfactin.

Suitable anionic surfactants may be selected from salts of fatty acids; alkali metal salts of mono- or dialkyl sulfates; mono- or dialkyl ether sulfates; lauryl ether sulfates; alkyl sulfonates; alkyl aryl sulfonates; primary alkane disulfonates; alkene sulfonates; hydroxyalkane sulfonates; alkyl glyceryl ether sulfonates; alpha-olefinsulfonates; alkyl phosphates; sulfonates of alkylphenolpolyglycol ethers; salts of alkyl sulfopolycarboxylic acid esters; alkyl sulfosuccinates and salts thereof, alkyl ether sulfosuccinates and salts thereof, acyl isethionates, alkylacyl isethionates, non-acylated alkyl isethionates; amino acid surfactants such as acyl and alkyl glutamates, acyl and alkyl sarcosinates, acyl and alkyl glycinates, acyl and alkyl alaninates and acyl and alkyl aspartates; products of condensation of fatty acids with oxy- and aminoalkanesulfonic acids; sulfated derivatives of fatty acids and polyglycols; alkyl sulfoacetates; alkyl phosphates; alkyl phosphate esters; acyl lactylates; alkanolamides of sulfated fatty acids and salts of lipoamino acids. Particularly exemplary salts of the above, where applicable, are the sodium, potassium, ammonium, magnesium and triethanolamine salts. Suitable ammonium cations include those derived from alkyl amines and alkanolamines. Preferred ammonium cations include isopropanolamine, isopropylamine, ethanolamine, diethanolamine, triethanolamine and 2-amino-2-methyl-1 ,3-propanediol (AMPD). Preferred ammonium cations include NF and the ammonium cation of triethanolamine.

Preferred anionic surfactants are selected from salts of fatty acids; alkyl sulfonates; alkyl aryl sulfonates; primary alkane disulfonates; alkene sulfonates; hydroxyalkane sulfonates; alkyl glyceryl ether sulfonates; alpha-olefinsulfonates; alkyl phosphates; sulfonates of alkylphenolpolyglycol ethers; salts of alkyl sulfopolycarboxylic acid esters; alkyl sulfosuccinates and salts thereof, alkyl ether sulfosuccinates and salts thereof, acyl isethionates, alkyl acyl isethionates, non-acylated alkyl isethionates; amino acid surfactants such as acyl and alkyl glutamates, acyl and alkyl sarcosinates, acyl and alkyl glycinates, acyl and alkyl alaninates and acyl and alkyl aspartates; products of condensation of fatty acids with oxy- and aminoalkanesulfonic acids; alkyl sulfoacetates; alkyl phosphates; alkyl phosphate esters; acyl lactylates; salts of lipoamino acids and biosurfactants, for example sophorolipids, rhamnolipids, saponins and surfactin.

Particularly exemplary salts of the above, where applicable, are the sodium, potassium, ammonium, magnesium and triethanolamine salts. Suitable ammonium cations include those derived from alkyl amines and alkanolamines. Preferred ammonium cations include isopropanolamine, isopropylamine, ethanolamine, diethanolamine, triethanolamine and 2- amino-2-methyl-1 ,3-propanediol (AMPD). Preferred ammonium cations include NF and the ammonium cation of triethanolamine.

Suitable sulfoacetates include acyl sulfoacetates, particularly sodium acyl sulfoacetates.

Suitable glutamate surfactants include monosodium or disodium acyl glutamates.

Suitable glycinate surfactants include monosodium acyl glycinates.

Suitable alaninate surfactants include monosodium acyl alaninates.

Suitable aspartate surfactants include monosodium or disodium acyl aspartates.

Preferred additional anionic detersive surfactants for use in the formulated compositions of the present invention include alkyl glyceryl ether sulfonate, ammonium lauryl sulfate, ammonium laureth sulfate, triethylamine lauryl sulfate, triethylamine laureth sulfate, triethanolamine lauryl sulfate, triethanolamine laureth sulfate, monoethanolamine lauryl sulfate, monoethanolamine laureth sulfate, diethanolamine lauryl sulfate, diethanolamine laureth sulfate, lauric monoglyceride sodium sulfate, sodium lauryl sulfate, sodium laureth sulfate, potassium lauryl sulfate, potassium laureth sulfate, sodium lauryl sarcosinate, sodium lauroyl sarcosinate, lauryl sarcosine, cocoyl sarcosine, ammonium cocoyl sulfate, ammonium lauroyl sulfate, sodium cocoyl sulfate, sodium lauroyl sulfate, potassium cocoyl sulfate, potassium lauryl sulfate, triethanolamine lauryl sulfate, triethanolamine lauryl sulfate, monoethanolamine cocoyl sulfate, monoethanolamine lauryl sulfate, sodium tridecyl benzene sulfonate, sodium dodecyl benzene sulfonate, and combinations thereof.

Suitable non-ionic surfactants for use in the formulated compositions of the present invention include alcohol alkoxylates such as alcohol ethoxylates, castor oil ethoxylates, alcohol propoxylates, and ethylene oxide/propylene oxide copolymer derived surfactants, aliphatic esters, aromatic esters, sugar esters, especially sorbitan esters, alkyl polyglucosides, fatty acid alkoxylates such as fatty acid ethoxylates and fatty acid propoxylates or polyethylene glycol esters and partial esters, glycerol esters including glycerol partial esters and glycerol triesters, fatty alcohols (such as cetearyl alcohol, lauryl alcohol, stearyl alcohol, behenyl alcohol), alkanolamides, amine oxides and biosurfactants, for example sophorolipids (lactonic form) and mannosylerythritol lipids.

Suitable non-ionic surfactants may be selected from the following: reaction products of compounds having a hydrophobic group and a reactive hydrogen atom, for example aliphatic alcohols, acids, amides or alkyl phenols with alkylene oxides, especially ethylene oxide either alone or with propylene oxide (for example alkyl (C6-C22) phenol-ethylene oxide condensates, the condensation products of aliphatic (Cs-Cis) primary or secondary linear or branched alcohols with ethylene oxide, and products made by condensation of ethylene oxide with the reaction products of propylene oxide and ethylenediamine); long chain tertiary amine oxides, long chain tertiary phosphine oxides and dialkyl sulfoxides; alkyl amine oxides, alkyl amido amine oxides; alkyl tertiary phosphine oxides; alkoxyl alkyl amines; sorbitan; sorbitan esters; sorbitan ester alkoxylates; glycerol ester alkoxylates; sucrose esters; sugar amides, such as a polysaccharide amide; lactobionamides; alkyl polysaccharide nonionic surfactants, for example alkylpolyglycosides and alkyl polypentosides; and biosurfactants from fermentation processes, for example sophorolipids (lactonic form) and mannosylerythritol lipids.

Suitable cationic surfactants for use in the formulated compositions of the present invention are typically based on fatty amine derivates or phosphonium quaternary ions, and quaternary ammonium compounds. Polymeric cationic surfactants may also be used.

Suitable cationic surfactants for use in the formulated compositions of the present invention include tertiary amine salts, mono alkyl trimethyl ammonium chloride, mono alkyl trimethyl ammonium methyl sulfate, dialkyl dimethyl ammonium chloride, dialkyl dimethyl ammonium methyl sulfate, trialkyl methyl ammonium chloride and trialkyl methyl ammonium methyl sulfate.

Examples of suitable cationic surfactants include quaternary ammonium compounds, particularly fatty-alkyl trimethyl quaternary compounds, difatty-alkyl dimethyl quaternary compounds and ester quaternary compounds.

Preferred quaternary ammonium compounds include cetyltrimethylammonium chloride, behenyltrimethylammonium chloride (BTAC), cetylpyridinium chloride, tetramethylammonium chloride, tetraethylammonium chloride, octyltrimethylammonium chloride, dodecyltrimethylammonium chloride, hexadecyltri methylammonium chloride, octyldimethylbenzylammonium chloride, decyldimethylbenzylammonium chloride, stearyldimethylbenzylammonium chloride, didodecyldimethylammonium chloride, dioctadecyldimethylammonium chloride, tallowtrimethylammonium chloride, cocotrimethylammonium chloride, PEG-2 oleylammonium chloride, ditallow dimethyl ammonium chloride, dicetyl dimethyl ammonium chloride, distearyl dimethyl ammonium chloride, ester quaternary ammonium compounds (examples of which are mentioned in J. Oleo Science, 56 (6), 269, (2007)) and salts of these where the chloride is replaced by halogen (e.g. bromide), acetate, citrate, lactate, glycolate, phosphate, nitrate, sulfate, alkylsulfate or alkyl sulfonate.

Further suitable cationic surfactants include those materials having the CTFA designations Quaternium-5, Quaternium-31 and Quaternium-18. Mixtures of any of the foregoing materials may also be suitable. A particularly useful cationic surfactant for use as a hair conditioning agent is cetyltrimethylammonium chloride, available commercially, for example as GENAMIN CTAC, Clariant.

Salts of primary, secondary, and tertiary fatty amines are also suitable cationic surfactants. The alkyl groups of such amines preferably have from 12 to 22 carbon atoms, and can be optionally substituted.

Useful cationic surfactants in this group include amido substituted tertiary fatty amines, in particular tertiary amines having one C12 to C22 alkyl or alkenyl chain. Such amines include stearamidopropyldimethylamine, stearamidopropyldiethylamine, stearamidoethyldiethylamine, stearamidoethyldimethylamine, palmitamidopropyldimethylamine, palmitamidopropyldiethylamine, palmitamidoethyldiethylamine, palmitamidoethyldimethylamine, behenamidopropyldimethylamine, behenamidopropyldiethylamine, behenamidoethyldiethylamine, behenamidoethyldimethylamine, arachidamidopropyldimethylamine, arachid amidopropyldiethylamine, arachidamidoethyldiethylamine, arachidamidoethyldimethylamine, diethylaminoethylstearamide.

Also useful are dimethylstearamine, dimethylsoyamine, soyamine, myristylamine, tridecylamine, ethylstearylamine, N-tallowpropane diamine, ethoxylated (with 5 moles of ethylene oxide) stearylamine, dihydroxyethylstearylamine, and arachidyl behenylamine.

These amines are typically used in combination with an acid to provide the cationic species. Suitable acids include L-glutamic acid, lactic acid, hydrochloric acid, malic acid, succinic acid, acetic acid, fumaric acid, tartaric acid, citric acid, L-glutamic hydrochloride, and mixtures thereof; more preferably L-glutamic acid, lactic acid, citric acid.

Other useful cationic amine surfactants include those disclosed in US4275055.

Suitable polymeric cationic surfactants include polyquaternium-7, polyquaternium-10, polyquaternium-11 , guar hydroxypropyltrimonium chloride, and hydroxypropyl guar hydroxypropyltrimonium chloride.

Suitable amphoteric surfactants for use in the formulated compositions of the present invention include those based on fatty nitrogen derivates and those based on betaines.

Suitable amphoteric or zwitterionic surfactants may be selected from betaines, for example alkyl betaines, alkylamidopropyl betaines, for example cocamidopropyl betaine, alkylamidopropyl hydroxy sultaines, alkylamphoacetates, alkylamphodiacetates, alkyl propionates, alkylamphodipropionates, alkylamphopropionates, alkyliminodipropionates, alkyliminodiacetate, dimethyl amine oxides and alkanoyl amidopropyldimethylamine oxides.

Amphoteric or zwitterionic surfactants for use in compositions of the fifth aspect may include those which have an alkyl or alkenyl group of 7 to 22 carbon atoms and comply with an overall structural formula:

where R⁷ is alkyl or alkenyl of 7 to 22 carbon atoms; R⁸ and R⁹ are each independently alkyl, hydroxyalkyl or carboxyalkyl of 1 to 6 carbon atoms; m is 2 to 4; n is 0 or 1 ; X is alkylene of 1 to 6 carbon atoms optionally substituted with hydroxyl; and Y is -CO2 or -SOs. Amphoteric or zwitterionic surfactants may include simple betaines of formula:

and amido betaines of formula:

where m is 2 or 3.

In both formulae R⁷, R⁸ and R⁹ are as defined previously. R⁷ may, in particular, be a mixture of C12 and Cu alkyl groups derived from coconut so that at least half, preferably at least three quarters, of the groups R⁷ has 10 to 14 carbon atoms. R⁸ and R⁹ are preferably methyl.

Amphoteric or zwitterionic surfactants may include sulfobetaines of formula:

R⁸

R⁷-N— (CH₂)₃SO₃-

R⁹

O R⁸

R⁷-C-NH(CH₂)_m— N— (CH₂)₃SO₃-

R⁹ where m is 2 or 3, or variants of these in which

-(CH2)3SO3^_ is replaced by

where R⁷, R⁸ and R⁹ in these formulae are as defined previously.

Amphoteric or zwitterionic surfactants may include amphoacetates and diamphoacetates. Amphoacetates generally conform to the following formula: R¹⁰CONHCH₂CH₂— N— CH₂CH₂OH CH₂COO^_ M₂ ⁺

Diamphoacetates generally conform to the following formula:

where R¹⁰ is an aliphatic group of 8 to 22 carbon atoms and M2⁺ is a cation such as sodium, potassium, ammonium, or substituted ammonium.

Suitable acetate-based surfactants include lauroamphoacetate; alkyl amphoacetate; sodium alkyl amphoacetate; cocoampho(di)acetate; cocoamphoacetate; disodium cocoamphodiacetate; sodium cocoamphoacetate; disodium cocoamphodiacetate; disodium capryloamphodiacete; disodium lauroamphoacetate; sodium lauroamphoacetate and disodium wheatgermamphodiacetate.

Suitable betaine surfactants include alkylamido betaine; alkyl betaine, C12/14 alkyldimethyl betaine; cocoamidopropylbetaine; tallow bis(hydroxyethyl) betaine; hexadecyldimethylbetaine; cocodimethylbetaine; alkyl amido propyl sulfo betaine; alkyl dimethyl amine betaine; coco amido propyl dimethyl betaine; alkyl amido propyl dimethyl amine betaine; cocamidopropyl betaine; lauryl betaine; laurylamidopropl betaine, coco amido betaine, lauryl amido betaine, alkyl amino betaine; alkyl amido betaine; coco betaine; lauryl betaine; diemethicone propyl PG-betaine; oleyl betaine; N-alkyldimethyl betaine; coco biguamide derivative, Cs amido betaine; C12 amido betaine; lauryl dimethyl betaine; alkylamide propyl betaine; amido betaine; alkyl betaine; cetyl betaine; oleamidopropyl betaine; isostearamidopropyl betaine; lauramidopropyl betaine; 2-alkyl- /V-carboxymethyl-/V-hydroxyethyl imidazolinium betaine; 2-alkyl-/V-carboxyethyl-/V-hydroxyethyl imidazolinium betaine; 2-alkyl-/V-sodium carboxymethyl-/V-carboxymethyl oxyethyl imidazolinium betaine; /V-alkyl acid amidopropyl-/V,/V-dimethyl-/V-(3-sulfopropyl)-ammonium- betaine; /V-alkyl-/V,/V-dimethyl-/V-(3-sulfopropyl)-ammonium-betaine; cocodimethyl betaine; apricotamidopropyl betaine; isostearamidopropyl betaine; myristamidopropyl betaine; palmitamidopropyl betaine; alkamidopropyl hydroxyl sultaine; cocamidopropyl hydroxyl sultaine; undecylenamidopropyl betaine; cocoamidosulfobetaine; alkyl amido betaine; C12/18 alkyl amido propyl dimethyl amine betaine; lauryldimethyl betaine; ricinol amidobetaine; tallow aminobetaine. Suitable amphoteric glycinate surfactants include acyl glycinates such as cocoamphocarboxyglycinate; tallowamphocarboxygycinate; capryloamphocarboxyglycinate, oleoamphocarboxyglycinate, bis-2-hydroxyethyl tallow glycinate; lauryl amphoglycinate; tallow polyamphoglycinate; coco amphoglycinate; oleic polyamphoglycinate; /V-C10/12 fatty acid amidoethyl-/V-(2-hydroxyethyl)-glycinate; /V-Ci2/is-fatty acid amidoethyl-N-(2-hydroxyethyl)- glycinate; dihydroxyethyl tallow gycinate.

Preferred acetate-based amphoteric surfactants include sodium lauroamphoacetate, disodium lauroamphoacetate and mixtures thereof.

Preferred betaine surfactants include cocoamidopropyl betaine.

Preferred sultaine surfactants include cocoamidopropylhydroxy sultaine.

The formulated composition comprises a surfactant composition and optionally one or more further surfactants.

Preferred further surfactants for inclusion in the formulated compositions of the present invention include those which are derived from renewable carbon sources.

The total RCI of the formulated composition is a weighted average of the RCI of each carbon- containing surfactant in the formulated composition. The %RCI is obtained by multiplying the RCI by 100. The term “surfactant” is well understood by a person skilled in the art and such a skilled person would readily understand which components of the formulated composition of the sixth aspect are surfactants.

Preferably total percentage RCI of the formulated composition is at least 30%, preferably at least 40%, more preferably at least 50%, suitably at least 60%, preferably at least 70% or at least 80%.

In some embodiments the total percentage RCI ofthe formulated composition is more than 85%, for example 90 to 100%, 95 to 100% or 98 to 100%.

The formulated composition ofthe present invention may be prepared by admixing the surfactant composition with the one or more further components. The preparation of formulated compositions can be simplified by the addition of a multi-component concentrate that contains more than one surfactant. Such materials can reduce the number of steps involved in the preparation of a formulated composition. According to a seventh aspect of the present invention there is provided a precursor concentrate composition comprising: a surfactant composition comprising one or more taurate compounds of formula (II):

wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R¹ represents an optionally substituted C3-C35 hydrocarbyl group; each of R², R³, R⁴, R⁵ and R⁶ independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR⁶CR²R³CR⁴R⁵SC>3X in the compound of formula (II) are from a renewable carbon source; and one or more further surfactants.

Preferred features of the seventh aspect of the present invention are as defined in relation to the first, second, third, fourth fifth and sixth aspects.

In particular preferred further surfactants for use in the precursor concentrate composition are as defined in relation to the sixth aspect.

Preferably the precursor concentrate composition comprises a total amount of from 20 to 60 wt% active surfactants, preferably from 30 to 50 wt%.

The precursor concentrate composition may be provided in any suitable form. In particularly preferred embodiments the precursor concentrate composition is a flowable liquid.

Preferred further surfactants for inclusion in the precursor concentrate compositions of the present invention include those which are derived from renewable carbon sources.

The total RCI of the precursor concentrate composition is a weighted average of the RCI of each carbon-containing surfactant in the precursor concentrate composition. Preferably the total percentage RCI of the precursor concentrate composition is at least 30%, preferably at least 40%, more preferably at least 50%, suitably at least 60%, preferably at least 70% or at least 80%.

In some embodiments the total percentage RCI of the precursor concentrate composition is more than 85%, for example 90 to 100%, 95 to 100% or 98 to 100%.

In preferred embodiments of the present invention the formulated composition of the sixth aspect of the present invention is a personal care composition.

The formulated personal care composition may comprise one or more foaming agents, emollients, dyes, fragrances, chelating agents, thickeners, conditioners, thickening agents, preservatives, antimicrobials, sequestrants, vitamins and derivatives thereof, sunscreens, desquamation actives, anti-wrinkle/ anti-atrophy actives, anti-oxidants, skin soothing agents/skin healing agents, skin lightening agents, skin tanning agents, anti-acne medicaments, essential oils, sensates, pigments, pearlescent agents and interference pigments.

Other optional materials can be those materials approved for use in cosmetics and that are described in the CTFA Cosmetic Ingredient Handbook, Second Edition, The Cosmetic, Toiletries, and Fragrance Association, Inc. 1988, 1992.

The formulated personal care composition may be a shampoo, conditioner, body wash, shower gel, moisturiser, cosmetic, skin care formulations or beauty bar.

The form of the formulated personal care composition will depend on the intended use thereof. It may be provided as a gel, paste, solid, liquid, emulsion or cream.

Preferably the formulated personal care composition comprises from 0.5 to 60 wt%, preferably from 1 to 40 wt%, suitably from 3 to 35 wt%, preferably from 5 to 30 wt%, for example from 6 to 20 wt% of one or more compounds of formula (II).

Preferably the formulated personal care composition comprises, in total, from 0.5 to 99 wt%, preferably from 1 to 80 wt% of active surfactant compounds. The amount of active surfactant compounds present in the composition will depend on the nature of the composition and the intended use thereof.

In some embodiments the formulated personal care composition may comprise, in total, from 5 to 50 wt%, or from 10 to 40 wt% of active surfactant compounds. In some preferred embodiments the formulated personal care composition of the present invention is a transparent composition. A transparent composition preferably transmits at least 90% of light having a wavelength of 600 nm.

In some preferred embodiments the formulated personal care compositions of the present invention are substantially sulfate-free.

Preferably the formulated personal care compositions comprise less than 1 wt% sulfate based surfactants, preferably less than 0.5 wt%, suitably less than 0.1 wt%, preferably less than 0.05 wt%, more preferably less than 0.01 wt%, for example less than 0.001 wt%

In some preferred embodiments the formulated personal care compositions of the present invention are low salt or salt-free.

Preferably the formulated personal care compositions comprise less than 1 wt% sodium chloride, preferably less than 0.5 wt%, suitably less than 0.1 wt%, preferably less than 0.05 wt%, more preferably less than 0.01 wt%, for example less than 0.001 wt%

According to an eighth aspect of the present invention there is provided a method of preparing a formulated composition of the sixth aspect, the method comprising preparing a surfactant composition according to the method of the first aspect and admixing said composition with one or more further components.

According to a ninth aspect of the present invention there is provided a method of preparing a formulated composition of the sixth aspect, the method comprising admixing a precursor concentrate composition of the seventh aspect with one or more further components.

The present invention offers significant advantage over the use of surfactants derived from petrochemical sources. As well as the obvious environmental benefits, the present invention may offer a reduction in the levels of impurities and reduced odours.

The invention will now be described with reference to the following non-limiting examples.

Example 1

Bio-taurine made by fermentation was diluted in water and the pH adjusted to 9-11 before adding an equimolar amount of lauroyl chloride synthesised from lauric acid. The mixture was heated at 40-60°C whilst maintaining a pH of 9-11 before cooling to ambient temperature to produce a white paste. The material had an RCI of 100%. %RCI calculation

The percentage renewable carbon index (%RCI) was obtained by dividing the number of carbon atoms derived from renewable carbon sources by the total number of carbon atoms. The %RCI of the compositions was obtained by taking a weighted average of the %RCI of each of the carbon-containing surfactant ingredients.

Example 2 A personal care composition was prepared comprising the following ingredients:

The composition had desirable foaming properties and skin feel and was mild to the skin and eyes.

Claims

1 . A method of preparing a taurate surfactant composition, the method comprising reacting a carboxylic acid of formula R¹COOH or a reactive equivalent thereof with a compound of formula (I):

wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R¹ represents an optionally substituted C3-C35 hydrocarbyl group; each of R², R³, R⁴, R⁵ and R⁶ independently represents hydrogen or a C1-C4 alkyl group; wherein the compound of formula (I) has a percentage renewable carbon index (RCI) of at least 50%.

2. A method according to claim 1 wherein the compound of formula (I) has a percentage renewable carbon index (RCI) of 95 to 100%.

3. A method according to claim 1 or claim 2 wherein the carboxylic acid of formula R¹COOH or a reactive equivalent thereof has a percentage renewable carbon index (RCI) of 95 to 100%.

4. A surfactant composition comprising one or more taurate compounds of formula (II):

wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R¹ represents an optionally substituted C3-C35 hydrocarbyl group; each of R², R³, R⁴, R⁵ and R⁶ independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR⁶CR²R³CR⁴R⁵SC>3X in the compound of formula (II) are from a renewable carbon source.

5. A compound of formula (II):

6. A compound of formula (I):

wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; each of R², R³, R⁴, R⁵ and R⁶ independently represents hydrogen or a C1-C4 alkyl group and wherein at least one of R², R³, R⁴, R⁵ and R⁶ is not hydrogen; wherein at least 50% of the carbon atoms in the compound are from a renewable carbon source

7. The use of a surfactant composition comprising one or more taurate compounds of formula (II):

8. A formulated composition comprising: a surfactant composition comprising one or more taurate compounds of formula (II):

wherein X is hydrogen, a metal ion or an optionally substituted ammonium ion; R¹ represents an optionally substituted C3-C35 hydrocarbyl group; each of R², R³, R⁴, R⁵ and R⁶ independently represents hydrogen or a C1-C4 alkyl group; wherein at least 50% of the carbon atoms provided by the moiety NR⁶CR²R³CR⁴R⁵SC>3X in the compound of formula (II) are from a renewable carbon source; and one or more further components.

9. A precursor concentrate composition comprising: a surfactant composition comprising one or more taurate compounds of formula (II):

10. A surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any of claims 4 to 9 wherein from 95 to 100% or 98 to 100% of the carbon atoms provided by the moiety NR⁶CR²R³CR⁴R⁵SC>3X in the compound of formula (II) are from a renewable carbon source.

11. A surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any of claims 4 to 10 where the compound of formula (II) has a percentage renewable carbon index (%RCI) of from 95 to 100%, preferably from 99 to 100%.

12. A method, surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any preceding claim wherein R¹ is provided by one or more naturally occurring fatty acids.

13. A method, surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any preceding claim wherein R¹ is provided by one or more fatty acids selected from coco acid, hexanoic acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, arachidic acid, gadoleic acid, arachidonic acid, eicosapentanoic acid, behenic acid, erucic acid, docosahexanoic lignoceric acid, naturally occurring fatty acids such as those obtained from coconut oil, tallow, palm kernel oil, butterfat, palm oil, olive oil, corn oil, linseed oil, peanut oil, fish oil and rapeseed oil.

14. A method, surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any preceding claim wherein R⁶ is Ci to C4 alkyl, preferably methyl.

15. A method, surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any of claims 1 to 13 wherein R⁶ is hydrogen.

16. A method, surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any preceding claim wherein one of the groups R², R³, R⁴ and R⁵ represents an optionally substituted C1-C4 alkyl group (preferably methyl) and the remaining groups represent hydrogen.

17. A method, surfactant composition, use, compound, formulated composition or precursor concentrate composition according to claim 16 which comprises a mixture of isomers comprising a compound of formula R¹CONR⁶CH2CHR⁴SC>3X in which each of R⁶ and R⁴ represents a Ci- 04 alkyl group (preferably methyl) and a compound of formula R¹CONR⁶CHR2CH2SO3X in which each of R⁶ and R² represents a C1-C4 alkyl group (preferably methyl); preferably wherein in at least 90% of compounds R² is methyl and R⁴ is hydrogen and at most 10% of compounds R² is hydrogen and R⁴ is methyl.

18. A method, surfactant composition, compound, use, formulated composition or precursor concentrate composition according to any of claims 1 to 15 wherein each of R², R³, R⁴ and R⁵ is hydrogen.

19. A formulated composition according to any of claims of 8 or 10 to 18 wherein the one or more further components are selected from chelating agents, preservatives, pH modifiers, hydrotropes and further surfactants.

20. A formulated composition according to claim 19 which comprises one or more further surfactants.

21 . A formulated composition according to claim 20 wherein the total percentage RCI of the formulated composition is at least 80%.

22. A method of preparing a formulated composition according to any of claims 8 or 10 to 21 , the method comprising preparing a surfactant composition according to the method of any of claims 1 to 3 and admixing said composition with one or more further components.

23. A precursor concentrate composition according to any of claims 9 to 18 wherein the total percentage RCI of precursor concentrate composition is at least 80%.

24. A method of preparing a formulated composition according to any of claims 8 to 21 , the method comprising admixing a precursor concentrate composition of any of claims 9 to 18 or 23 with one or more further components.