Polymers

Abstract

Polymers A polymer, wherein the polymer is the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is a hydroxycarboxylic acid or a cyclic ester thereof and the or each second monomer is one or more of the following: (i) cyclic anhydride; (ii) polycarboxylic acid or reactive equivalent thereof; (iii) monocarboxylic acid or ester thereof; (iv) polyol; (v) epoxide compound; (vi) polyfunctional monomer having a reactive amino group; (vii) monoalcohol; and (viii) monofunctional monomer having a reactive amino group.

Description

[0001] Polymers

[0002] Field

[0003] The present invention relates to polymers and to concentrate compositions comprising the polymer.

[0004] Background

[0005] Silicone compounds, such as polydimethylsiloxane, functionalised polydimethylsiloxanes, organosilicones, and related compounds are used widely in a range of applications and products. They may be provided in concentrate compositions, either for direct use or for later dilution priorto use. However, high concentrations of silicone compounds can cause concentrate compositions to be highly viscous and difficult to pour or pump. Furthermore, high concentrations of the silicone compound can cause concentrate compositions to be unstable when stored for extended periods of time, especially when the silicone compound is poorly soluble or poorly miscible with a diluent comprised in the concentrate composition.

[0006] There are a number of disadvantages associated with the use of such silicone compounds, including their low biodegradability, which has led to environmental concerns.

[0007] It is thus an object of the invention to provide an alternative to silicone compounds that can be used in a wide range of applications and uses. It is another object of the invention to provide alternatives to silicone compounds that are more biodegradable whilst having equal or improved properties. It is another object of the invention to improve the stability and / or flowability of concentrate compositions comprising such compounds.

[0008] Summary of the Invention

[0009] According to aspects of the present invention, there is provided a polymer, method and concentrate composition as set forth in the appended claims. Other features of the invention will be apparent from the dependent claims, and from the description which follows.

[0010] The inventors have identified that certain polymers have properties that are at least comparable to that provided by known silicone compounds, whilst also being more biodegradable.

[0011] According to a first aspect of the invention, there is provided a polymer, wherein the polymer is the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is a hydroxycarboxylic acid or a cyclic ester thereof and the or each second monomer is one or more of the following: (i) cyclic anhydride;

[0012] (ii) polycarboxylic acid or reactive equivalent thereof;

[0013] (iii) monocarboxylic acid or ester thereof;

[0014] (iv) polyol;

[0015] (v) epoxide compound;

[0016] (vi) polyfunctional monomer having a reactive amino group;

[0017] (vii) monoalcohol; and

[0018] (viii) monofunctional monomer having a reactive amino group.

[0019] According to a second aspect of the invention, there is provided a concentrate composition comprising one or more polymers and optionally at least one solvent, wherein the concentrate composition comprises at least 20 wt% of the one or more polymers, and wherein the or each polymer is the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is a hydroxycarboxylic acid or a cyclic ester thereof and the or each second monomer is one or more of the following:

[0020] (i) cyclic anhydride;

[0021] (ii) polycarboxylic acid or reactive equivalent thereof;

[0022] (iii) monocarboxylic acid or ester thereof;

[0023] (iv) polyol;

[0024] (v) epoxide compound;

[0025] (vi) polyfunctional monomer having a reactive amino group;

[0026] (vii) monoalcohol; and

[0027] (viii) monofunctional monomer having a reactive amino group.

[0028] According to a third aspect of the invention, there is provided a use of a surfactant to emulsify at least one polymer in an aqueous concentrate composition, wherein the aqueous concentrate composition comprises at least 20 wt% of the one or more polymers, and wherein the polymer is the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is a hydroxycarboxylic acid or a cyclic ester thereof and the or each second monomer is one or more of the following:

[0029] (i) cyclic anhydride;

[0030] (ii) polycarboxylic acid or reactive equivalent thereof;

[0031] (iii) monocarboxylic acid or ester thereof;

[0032] (iv) polyol;

[0033] (v) epoxide compound;

[0034] (vi) polyfunctional monomer having a reactive amino group;

[0035] (vii) monoalcohol; and

[0036] (viii) monofunctional monomer having a reactive amino group. According to a fourth aspect of the invention, there is provided a method of emulsifying at least one polymer in an aqueous composition to make an aqueous polymer concentrate composition, wherein the aqueous polymer concentrate composition comprises at least 20 wt% of the one or more polymers, the method comprising admixing a surfactant with the polymer in an aqueous composition, wherein the polymer is the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is a hydroxycarboxylic acid or a cyclic ester thereof and the or each second monomer is one or more of the following:

[0037] (i) cyclic anhydride;

[0038] (ii) polycarboxylic acid or reactive equivalent thereof;

[0039] (iii) monocarboxylic acid or ester thereof;

[0040] (iv) polyol;

[0041] (v) epoxide compound;

[0042] (vi) polyfunctional monomer having a reactive amino group;

[0043] (vii) monoalcohol; and

[0044] (viii) monofunctional monomer having a reactive amino group.

[0045] Other features of the invention will be apparent from the dependent claims, and from the description which follows.

[0046] Features described in relation to the second, third and fourth aspects may have any of the suitable features and advantages described in relation to the first aspect.

[0047] Detailed Description of the Invention

[0048] Unless otherwise stated, the following terms used in the specification and claims have the meanings set out below.

[0049] The terms “alkyl” and “alkylene” include both straight and branched chain alkyl and alkylene groups respectively unless otherwise stated.

[0050] References to individual alkyl groups such as “propyl” are specific for the straight chain version only and references to individual branched chain alkyl groups such as “isopropyl” are specific for the branched chain version only. For example, “C3-30 alkyl” includes Ce-24 alkyl, Ce-s alkyl, propyl, isopropyl and t-butyl.

[0051] The term “alkenyl” includes both straight and branched chain alkenyl groups. References to individual alkenyl groups such as “propenyl” are specific for the straight chain version only and references to individual branched chain alkenyl groups such as “isopropenyl” are specific for the branched chain version only. For example, “C3-30 alkenyl” includes Ce-24 alkenyl, Ce-s alkenyl, propenyl and isopropenyl.

[0052] Herein C3-30 means a group having from 3 to 30 carbons atoms therein, for example having 3, 4, 5 etc up to 30 carbon atoms.

[0053] The term "hydrocarbyl" is used in its ordinary sense, which is well-known to those skilled in the art. Specifically, it refers to a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character.

[0054] As used in the specification and the appended claims, the singular forms "a", "an," and "the" include both singular and plural referents unless the context clearly dictates otherwise.

[0055] Throughout this specification, the term “comprising” or “comprises” means including the component(s) specified but not to the exclusion of the presence of other components. The term “consisting essentially of’ or “consists essentially of’ means including the components specified but excluding other components except for components added for a purpose other than achieving the technical effect of the invention. The term “consisting of’ or “consists of’ means including the components specified but excluding other components.

[0056] Whenever appropriate, depending upon the context, the use of the term “comprises” or “comprising” may also be taken to include the meaning “consists essentially of’ or “consisting essentially of’, and also may also be taken to include the meaning “consists of’ or “consisting of’.

[0057] As used herein, unless otherwise expressly specified, all numbers such as those expressing values, ranges, amounts of percentages may be read as if prefaced by the word “about”, even if the term does not expressly appear.

[0058] The recitation of numerical ranges by endpoints includes all integer numbers and, where appropriate, fractions subsumed within that range (e.g. 1 to 5 can include 1 , 2, 3, 4 when referring to, for example, a number of elements, and can also include 1.5, 2, 2.70 and 3.80, when referring to, for example, measurements). The recitation of end points also includes the end point values themselves (e.g. from 1.0 to 5.0 includes both 1.0 and 5.0). Any numerical range recited herein is intended to include all sub-ranges subsumed therein.

[0059] The optional features set out herein may be used either individually or in combination with each other where appropriate and particularly in the combinations as set out in the accompanying claims. The optional features for each exemplary aspect of the invention, as set out herein are also applicable to any other aspects or exemplary aspects of the invention, where appropriate. In otherwords, the skilled person reading this specification should considerthe optional features for each aspect or embodiment of the invention as interchangeable and combinable between different aspects of the invention.

[0060] As used herein, the term "and / or," when used in a list of two or more items, means that any one of the listed items can be employed by itself or any combination of two or more of the listed items can be employed. For example, if a list is described as comprising group A, B, and / or C, the list can comprise A alone; B alone; C alone; A and B in combination; A and C in combination, B and C in combination; or A, B, and C in combination.

[0061] The term “monomer” is used herein to refer to a compound comprising at least one polymerisable functional group.

[0062] As reported herein, the number average molecular weight was determined by gel permeation chromatography using a polystyrene standard according to ASTM D6579-11 (“Standard Practice for Molecular Weight Averages and Molecular Weight Distribution of Hydrocarbon, Rosin and Terpene Resins by Size Exclusion Chromatography”. UV detector; 254 nm, solvent: unstabilised THF, retention time marker: toluene, sample concentration: 2mg / ml).

[0063] According to a first aspect of the invention, there is provided a polymer, wherein the polymer is the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is a hydroxycarboxylic acid or a cyclic ester thereof and the or each second monomer is one or more of the following:

[0064] (i) cyclic anhydride;

[0065] (ii) polycarboxylic acid or reactive equivalent thereof;

[0066] (iii) monocarboxylic acid or ester thereof;

[0067] (iv) polyol;

[0068] (v) epoxide compound;

[0069] (vi) polyfunctional monomer having a reactive amino group;

[0070] (vii) monoalcohol; and

[0071] (viii) monofunctional monomer having a reactive amino group.

[0072] Suitable features of the first aspect will now be described.

[0073] The polymer of the first aspect is the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers as defined herein. In otherwords, the polymer may be obtainable or obtained by polymerising monomers comprising one or more first monomers and optionally one or more second monomers as defined herein. Thus, the reaction product is a polymer comprising repeat units derived from the one or more first monomers and optionally repeat units derived from the one or more second monomers as defined herein.

[0074] When the polymer is the reaction product of monomers comprising one or more first monomers only (and no second monomers), the polymer may be a copolymer (i.e. made from two or more first monomers) or a homopolymer (i.e. made from only one first monomer).

[0075] Preferably when the polymer is the reaction product of monomers comprising one or more first monomers only (and no second monomers), the polymer is a copolymer (i.e. made from two or more first monomers).

[0076] It is preferred that the polymer is a copolymer. For example, it is preferred that the polymer is a copolymer comprising two or more first monomers (i.e. wherein the two or more first monomers are different) or is a copolymer comprising one or more first monomers and one or more second monomers, wherein the first and second monomer are as defined herein.

[0077] Preferably, the polymer is not a homopolymer made from ricinoleic acid as the (single) first monomer, i.e. preferably the polymer is not polyricinoleic acid.

[0078] Preferably, the polymer is not a homopolymer made from hydroxystearic acid as the (single) first monomer, i.e. preferably the polymer is not polyhydroxystearic acid.

[0079] Preferably, the polymer is not a homopolymer made from caprolactone as the (single) first monomer, i.e. preferably the polymer is not polycaprolactone.

[0080] When the polymer is the reaction product of monomers comprising one or more first monomers and one or more second monomers, the polymer is a copolymer. The copolymer may be made from one or more first monomers and one or more second monomers.

[0081] The polymer of the first aspect may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers as defined herein. In other words, the polymer may be obtainable or obtained by polymerising monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers as defined herein. Thus, the reaction product may be a polymer consisting essentially of or consisting of repeat units derived from the one or more first monomers and optionally the one or more second monomers as defined herein.

[0082] Typically, the polymerthat is the reaction product of the monomers defined herein is a polyester. The first and second monomers may be reacted in any suitable molar ratio to make the polymer, as would be appreciated by a person skilled in the art. Thus repeat units in the polymer derived from the first and second monomers may be present in the polymer in any suitable molar ratio and in any suitable arrangement.

[0083] The first and second monomers may be reacted in a molar ratio of from 1 :10 to 10:1 , preferably from 1 :6 to 6:1 , for example from 1 :3 to 3:1. Ratios refer to the total amounts of first monomers or second monomers if more than one first monomer or second monomer is present.

[0084] The polymer may be prepared by any suitable method, as would be known to persons skilled in the art.

[0085] Suitably, the polymer is not in a solid form. For example, the polymer is preferably in the form of a liquid or gel, preferably a liquid.

[0086] Suitably, the polymer herein that is the reaction product of monomers comprising one or more first monomers and one or more second monomers is substantially free or free of cross-linking.

[0087] In some embodiments, the polymer does not contain any nitrogen atoms.

[0088] References herein to a reaction product of monomers comprising the first and second monomers are intended to refer to a product of the reaction of monomers comprising the first and second monomers conducted in any suitable manner. For example, the reaction may occur between the first and second monomers in the absence of other monomer(s) or may occur in the presence of other monomer(s).

[0089] The or each of the one or more first monomers used to make the polymer is a hydroxycarboxylic acid or a cyclic ester thereof. Mixtures of two or more different first monomers (i.e. different hydroxycarboxylic acid or a cyclic ester thereof) may be used to make the polymer.

[0090] Any suitable hydroxycarboxylic acid or a cyclic ester thereof may be used to make the polymer, as would be understood by the person skilled in the art.

[0091] The first monomer may be a hydroxycarboxylic acid or a cyclic ester thereof.

[0092] The first monomer may preferably be a hydroxycarboxylic acid. The hydroxycarboxylic acid suitably comprises one or more hydroxy groups and one or more carboxylic acid groups.

[0093] The hydroxycarboxylic acid may be a monocarboxylic acid comprising one or more hydroxy groups.

[0094] The hydroxycarboxylic acid may be of the formula R(CR2)nCOOH, wherein n is from 1 to 30 and each R is independently hydrogen, a hydroxy group, or a substituent otherthan a hydroxy group, and when n is 2 or more, two R groups on adjacent carbon atoms may optionally be taken together to form a double bond, wherein at least one of the R groups is a hydroxy group.

[0095] n is suitably from 1 to 25, preferably from 1 to 20, more preferably from 1 to 17.

[0096] Each (CR2) group can be the same or different.

[0097] Unless otherwise specified, the terms “each R”, “R groups” and the like are intended to refer to all instances of the “R” group in the formula R(CR2)nCOOH, including the R groups in the (CR2)n group and the terminal R group outside of the (CR2)n group.

[0098] In addition to at least one of the R groups being a hydroxy group, at least one of the R groups may be a substituent other than a hydroxy group. Any suitable substituent may be used. The substituent may be a hydrocarbyl group or a heteroatom-containing group. By the term “heteroatom” we mean an atom other than carbon or hydrogen, such as oxygen or nitrogen. Examples of suitable substituents include amino groups, carboxyl groups, alkyl groups, alkenyl groups, aryl groups, aralkyl groups, and alkaryl groups, wherein the alkyl groups, alkenyl groups, aryl groups, aralkyl groups, and alkaryl groups are optionally substituted with one or more of a hydroxy group, an amino group, and / or a carboxyl group.

[0099] Suitably, one or two (preferably one) R groups are a hydroxy group and the remaining R groups are each independently hydrogen or a substituent otherthan a hydroxy group.

[0100] One or two (preferably one) R groups may be a hydroxy group and each of the remaining R groups may be hydrogen. The hydroxycarboxylic acid may be selected from glycolic acid, lactic acid, hydroxy butyric acid, hydroxyvaleric acid, hydroxycaproic acid, hydroxystearic acid (preferably 12-hydroxystearic acid), or dihydroxystearic acid.

[0101] Alternatively, one or two (preferably one) R groups may be a hydroxy group, at least one of the R groups may be a substituent otherthan a hydroxy group, and the remaining R groups may be hydrogen. For example, one or two of the R groups may be a substituent other than a hydroxy group.

[0102] One or two (preferably one) of the R groups may be a hydroxy group, one or two of the R groups may each independently be an alkyl group, a hydroxy-substituted alkyl group, or an aryl group, and the remaining R groups may be hydrogen. The hydroxycarboxylic acid may be 2,2-bis(hydroxymethyl)propionic acid or mandelic acid.

[0103] When n is 2 or more, two R groups on adjacent carbon atoms may be taken together to form a double bond. The hydroxycarboxylic acid may comprise one or more such double bonds. The double bond may be in a cis or trans configuration. At least one R (preferably one) may be a hydroxy group, two R groups on adjacent carbon atoms may be taken together to form a double bond and the remaining R groups may be hydrogen. The hydroxycarboxylic acid may be ricinoleic acid.

[0104] The hydroxycarboxylic acid may comprise two or more carboxylic acid groups.

[0105] The hydroxycarboxylic acid may be of the formula HOOC(CR’2)nCOOH, wherein n is from 1 to 30 and each R’ is independently hydrogen, a hydroxy group, or a substituent other than a hydroxy group, wherein at least one of the R’ groups is a hydroxy group.

[0106] Suitable features of the hydroxycarboxylic acid of the formula HOOC(CR’2)nCOOH will now be described.

[0107] n is suitably from 1 to 20, preferably from 2 to 16, more preferably from 2 to 12, for example from 2 to 10.

[0108] Each (CR’2) group can be the same or different.

[0109] Unless otherwise specified, the terms “each R’”, “R’ groups” and the like are intended to refer to all instances of the “R”’ group in the formula HOOC(CR’2)nCOOH.

[0110] In addition to at least one of the R’ groups being a hydroxy group, at least one of the R’ groups may be a substituent other than a hydroxy group. Any suitable substituent may be used. The substituent may be a hydrocarbyl group ora heteroatom-containing group. Examples of suitable substituents include amino groups, carboxyl groups, alkyl groups, alkenyl groups, aryl groups, aralkyl groups, and alkaryl groups, wherein the alkyl groups, alkenyl groups, aryl groups, aralkyl groups, and alkaryl groups are optionally substituted with one or more of a hydroxy group, an amino group, and / or a carboxyl group. Suitably, one or two R’ groups are a hydroxy group and the remaining R’ groups are each independently hydrogen or a substituent other than a hydroxy group.

[0111] One or two R’ groups may be a hydroxy group and each of the remaining R’ groups may be hydrogen.

[0112] Alternatively, one or two R’ groups may be a hydroxy group, one or two of the R’ groups may be a substituent other than a hydroxy group, and the remaining R’ groups may be hydrogen.

[0113] One or two of the R’ groups may be a hydroxy group, one of the R’ groups may optionally be a carboxyl group or a carboxyl-substituted methyl group, and the remaining R’ groups may be hydrogen. The hydroxycarboxylic acid may be malic acid, tartaric acid, or citric acid.

[0114] The or each hydroxycarboxylic acid may be hydroxystearic acid (preferably 12-hydroxystearic acid) or ricinoleic acid. Preferably, the hydroxycarboxylic acid may be ricinoleic acid.

[0115] The first monomer may be a cyclic ester of a hydroxycarboxylic acid. The hydroxycarboxylic acid may suitably be as described above.

[0116] By the term “cyclic ester” of a hydroxycarboxylic acid we mean a compound comprising a cyclic group, wherein the cyclic group comprises one or more ester groups. The ester may be a cyclic monoester or a cyclic diester. The cyclic ester may correspond to a single cyclised molecule of the hydroxycarboxylic acid. This may, for example, be formed by an intramolecular reaction between the hydroxy group and the carboxylic acid group on one molecule of the hydroxycarboxylic acid. Alternatively, the cyclic ester may correspond to a cyclic dimer of a hydroxycarboxylic acid. This may, for example, be formed by an intermolecular reaction between the hydroxy groups and the carboxylic acid groups on two molecules of the hydroxycarboxylic acid.

[0117] The first monomer may be a cyclic ester of formula (I) or (II):

[0118]

[0119] wherein R1is hydrogen or a hydrocarbyl group;

[0120] each R2is independently hydrogen or a hydrocarbyl group;

[0121] n2 is from 1 to 29;

[0122] each R3is independently hydrogen or a hydrocarbyl group;

[0123] n3 is from 1 to 29;

[0124] each R4is independently hydrogen or a hydrocarbyl group; and

[0125] n4 is from 1 to 29.

[0126] R1may be a hydrocarbyl group. The hydrocarbyl group suitably contains from 1 to 12 carbon atoms, such as from 1 to 6 carbon atoms. The hydrocarbyl group may be an alkyl, alkenyl, aryl, aralkyl, or alkaryl group.

[0127] R1may be an alkyl group. The alkyl group suitably contains from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms. R1may be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, ort-butyl.

[0128] R1is preferably hydrogen.

[0129] Each R2is independently hydrogen or a hydrocarbyl group. The hydrocarbyl group suitably contains from 1 to 12 carbon atoms, such as from 1 to 6 carbon atoms. The hydrocarbyl group may be an alkyl, alkenyl, aryl, aralkyl, or alkaryl group.

[0130] Each R2may independently be hydrogen or an alkyl group. The alkyl group suitably contains from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms. R2may be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, ort-butyl.

[0131] Each R2may be hydrogen. Alternatively, at least one R2may be a hydrocarbyl group, preferably an alkyl group, and any remaining R2groups may be hydrogen. n2 is suitably from 1 to 20, preferably from 1 to 10, such as from 2 to 5. Preferably, n2 is 3 or 4.

[0132] Each R3is independently hydrogen or a hydrocarbyl group. The hydrocarbyl group suitably contains from 1 to 12 carbon atoms, such as from 1 to 6 carbon atoms. The hydrocarbyl group may be an alkyl, alkenyl, aryl, aralkyl, or alkaryl group.

[0133] Each R3may independently be hydrogen or an alkyl group. The alkyl group suitably contains from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms. R3may be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, ort-butyl.

[0134] Preferably at least one R3is a hydrocarbyl group, such as methyl.

[0135] n3 is from 1 to 20, preferably from 1 to 10, such as 1 or 2. Preferably, n3 is 1 .

[0136] Each R4is independently hydrogen or a hydrocarbyl group. The hydrocarbyl group suitably contains from 1 to 12 carbon atoms, such as from 1 to 6 carbon atoms. The hydrocarbyl group may be an alkyl, alkenyl, aryl, aralkyl, or alkaryl group.

[0137] Each R4may independently be hydrogen or an alkyl group. The alkyl group suitably contains from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms. R4may be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, ort-butyl.

[0138] Preferably at least one R4is a hydrocarbyl group, such as methyl.

[0139] n4 is from 1 to 20, preferably from 1 to 10, such as 1 or 2. Preferably, n4 is 1 .

[0140] Preferably, -(CHR3)n2- and -(CHR4)n3- in formula (II) are the same.

[0141] Suitably, the first monomer may be a cyclic ester of formula (I) or (II) wherein:

[0142] R1is hydrogen;

[0143] each R2is independently hydrogen or an alkyl group;

[0144] n2 is from 2 to 5;

[0145] each R3is independently hydrogen or a hydrocarbyl group wherein at least one R3is a hydrocarbyl group;

[0146] n3 is 1 or 2;

[0147] each R4is independently hydrogen or a hydrocarbyl group wherein at least one R4is a hydrocarbyl group; and

[0148] n4 is 1 or 2. The cyclic ester may be a lactone. Examples of suitable lactones include y-butyrolactone, 6-valerolactone, e-caprolactone, menthide, D-lactide, L-lactide, and DL-lactide. Preferably, the lactone is e-caprolactone, menthide, or DL-lactide.

[0149] Suitably, the or each hydroxycarboxylic acid or the cyclic ester thereof may be selected from glycolic acid, lactic acid, hydroxy butyric acid, hydroxyvaleric acid, hydroxycaproic acid, hydroxystearic acid (preferably 12-hydroxystearic acid), dihydroxystearic acid, 2,2-bis(hydroxymethyl)propionic acid, mandelic acid, ricinoleic acid, malic acid, tartaric acid, citric acid, y-butyrolactone, b-valerolactone, e-caprolactone, menthide, D-lactide, L-lactide, or DL-lactide.

[0150] Preferably, the or each hydroxycarboxylic acid or the cyclic ester thereof may be selected from glycolic acid, mandelic acid, ricinoleic acid, malic acid, tartaric acid, citric acid, e-caprolactone, menthide, or DL-lactide (especially glycolic acid, ricinoleic acid, malic acid and citric acid; most preferably citric acid, malic acid and ricinoleic acid).

[0151] In some embodiments, mixtures of two or more different first monomers may be used to make the polymer. For example, the one or more first monomers may comprise a mixture of DL-lactide and citric acid or e-caprolactone. Alternatively, the one or more first monomers may comprise a mixture of ricinoleic acid and a further hydroxycarboxylic acid selected from glycolic acid, mandelic acid, malic acid, or citric acid.

[0152] Preferably, the or each first monomer is a hydroxycarboxylic acid as disclosed herein (and not a cyclic ester thereof).

[0153] The hydroxycarboxylic acid or a cyclic ester thereof compounds discussed herein may be commercially available or may be prepared using procedures well known in the art.

[0154] Optionally, one or more second monomers may be used to make the polymer. Preferably, the polymer is the reaction product of monomers comprising one or more first monomers as defined herein and one or more second monomers as defined herein. References herein to the second monomers are intended to refer to the polymer when one or more second monomers are used to make the polymer.

[0155] The or each of the one or more second monomers (when present) used to make the polymer is one or more of the following:

[0156] (i) cyclic anhydride;

[0157] (ii) polyol;

[0158] (iii) polycarboxylic acid or reactive equivalent thereof; (iv) monocarboxylic acid or ester thereof;

[0159] (v) epoxide compound;

[0160] (vi) polyfunctional monomer having a reactive amino group;

[0161] (vii) monoalcohol; and

[0162] (viii) monofunctional monomer having a reactive amino group.

[0163] Preferably, the or each of the one or more second monomers (when present) used to make the polymer may be one or more of the following:

[0164] (i) polyol; and

[0165] (ii) monoalcohol.

[0166] Preferably, the or each of the one or more second monomers (when present) used to make the polymer may be one or more monoalcohol.

[0167] Mixtures of two or more different second monomers may be used to make the polymer. For example, two or more of any of the monomers (i) to (viii) as defined herein may be used, and / or two or more of each of the monomers (ii), (ii) etc may be used.

[0168] Any suitable monomer (i) to (viii) as defined herein may be used to make the polymer, as would be understood by the person skilled in the art.

[0169] The one or more second monomers (when present) are different to the one or more first monomers. Thus, any monomer that represents a hydroxycarboxylic acid or a cyclic ester thereof is considered herein to be a first monomer, and not a second monomer. For example, when ricinoleic acid and glycolic acid are used to make the polymer, they are both considered to belong to the group of first monomers and not to the group of second monomers, such as monoalcohols or monocarboxylic acids or esters thereof. In otherwords, the one or more second monomers are not hydroxycarboxylic acids or cyclic esters thereof.

[0170] One or more of the second monomers may be a cyclic anhydride.

[0171] By the term cyclic anhydride we mean a compound (or monomer) that comprises at least one anhydride group that is contained within a ring structure. For example, the ring structure that contains the anhydride group may comprise from 4 to 8 atoms, which atoms are typically carbon and oxygen. The ring structure that contains the anhydride group may be saturated or partially unsaturated, (and is preferably saturated). The cyclic anhydride compound may typically comprise more than 8 atoms. For example, suitable cyclic anhydrides may include one or more of an anhydride of formula (III), of formula (IV) and of formula (V):

[0172]

[0173] wherein in formula (III) R5and R6are each independently selected from hydrogen, an alkyl group and an alkenyl group, or R5and R6together with the carbon atoms to which they are attached represent an optionally substituted cyclic group;

[0174] in formula (IV) R7and R8are each independently selected from hydrogen, an alkyl group and an alkenyl group, or R7and R8together with the carbon atoms to which they are attached represent an optionally substituted cyclic group; and

[0175] in formula (V) X is CR13R14, O, S, or NR15; R9, R10, R11, R12, R13, R14, and R15are each independently selected from hydrogen, an alkyl group and an alkenyl group, and / or any of R9, R10, R11, R12, R13, R14, and R15together with the atoms to which they are attached represent an optionally substituted cyclic group.

[0176] Cyclic anhydrides of formula (III) are preferred.

[0177] X may suitably be CR13R14, O, or S. Preferably, X is CR13R14.

[0178] When any of R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, and R15represents an alkyl group or an alkenyl group, the or each alkyl or alkenyl group may be branched or unbranched. The or each alkyl group may contain from 1 to 30 carbon atoms and the or each alkenyl group may contain from 2 to 30 carbon atoms. Preferably, each alkyl or alkenyl group may contain 6 or more carbon atoms. For example, the or each alkyl or alkenyl group may contain from 6 to 30, such as from 8 to 24, carbon atoms (i.e. may be a Ce-3o, such as a Cs-24, alkyl or alkenyl group).

[0179] When any of R5and R6, or R7and R8, orR9, R10, R11, R12, R13, and R14represents an alkenyl group, the alkenyl group may be a polyisobutenyl group. The polyisobutenyl group (when present) suitably has a number average molecular weight of from 100 to 2000, preferably from 100 to 1000, for example 260 or 550. The cyclic anhydride may be a polyisobutenyl succinic anhydride, for example wherein the polyisobutenyl group has a number average molecular weight of 260 or 550.

[0180] When any of R5and R6, or R7and R8, orR9, R10, R11, R12, R13, and R14represents an alkenyl group, the alkenyl group may be derived from a terminal olefin or an internal olefin. For example, the cyclic anhydride monomer may be an alkenyl substituted succinic anhydride prepared by the reaction of an alkene with maleic anhydride, wherein the alkene is a terminal olefin or an internal olefin.

[0181] In some embodiments the alkenyl group may be derived from a terminal olefin. The term terminal olefin is used to refer to alkene compounds having a predominantly terminal double bond. Such compounds are also commonly described as terminal alkenes. Terminal double bonds terminate in a =CH2group and may either be at the a-position or may be vinylidene groups. The terminal olefin is preferably an a-olefin. Examples of suitable terminal olefins include C12 terminal olefin, C15-18 terminal olefin, Cw terminal olefin and Cw terminal olefin.

[0182] In some preferred embodiments the alkenyl group is derived from an internal olefin. The term internal olefin is used to refer to alkene compounds in which the alkene groups are predominantly not terminal. Examples of suitable internal olefins include C12 internal olefin, Cisis internal olefin, C internal olefin and Cw internal olefin.

[0183] The internal olefin is a or higher olefin, such as a p-olefin.

[0184] Internal olefins are sometimes known as isomerised olefins and may be prepared by isomerisation of an a-olefin.

[0185] Typically, terminal olefins and internal olefins may be provided as a mixture of isomers. Suitably at least 70 mol%, such as at least 80 mol%, preferably at least 90 mol%, for example at least 95 mol% of the double bonds in terminal olefins are terminal double bonds. Suitably at least 70 mol%, such as at least 80 mol%, preferably at least 90 mol%, for example at least 95 mol% of the terminal double bonds in the terminal olefins are at the a-position (i.e. they are a-alkene groups). Suitably at least 70 mol%, such as at least 80 mol%, preferably at least 90 mol%, for example at least 95 mol% of the double bonds in internal olefins are non-terminal double bonds.

[0186] Suitably, one of R5and R6, R7and R8, or R9, R10, R11, R12, R13, R14, and R15may be an alkyl group or an alkenyl group (such as an alkenyl group derived from a terminal olefin or an internal olefin, preferably an internal olefin) and the other (or others) may be hydrogen. Examples of cyclic anhydride monomers of the formula (I), (II) or (III) wherein any of R1and R2, R3and R4, or R5, R6, R7, R8, R9, R10, and R11represents hydrogen or a Ce-3o, such as a Cs-24, branched or unbranched alkyl or alkenyl group include succinic anhydride, dodecenyl succinic anhydride (such as (2-dodecen-1-yl)succinic anhydride), tetrapropenyl succinic anhydride, octadecenyl succinic anhydride, octenyl succinic anhydride, nonenyl succinic anhydride, C20-24 alkenyl succinic anhydride, C15-18 internal olefin-derived alkenyl succinic anhydride, Cw internal olefin-derived alkenyl succinic anhydride, C terminal olefin-derived alkenyl succinic anhydride, maleic anhydride and glutaric anhydride.

[0187] The cyclic anhydride monomers of the formula (III), (IV) or (V) wherein any of R5and R6, R7and R8, or R9, R10, R11, R12, R13, R14, and R15represents hydrogen or a Cs-3o, such as a Cs-24, branched or unbranched alkyl or alkenyl group may be selected from succinic anhydride, dodecenyl succinic anhydride (such as (2-dodecen-1-yl)succinic anhydride), tetrapropenyl succinic anhydride, octadecenyl succinic anhydride, octenyl succinic anhydride, nonenyl succinic anhydride, C 20-24 alkenyl succinic anhydride, maleic anhydride and glutaric anhydride.

[0188] When any of R5and R6, or R7and R8, or R9, R10, R11, R12, R13, R14, and R15, together with the atoms to which they are attached represent an optionally substituted cyclic group, the cyclic group so formed may be mono or polycyclic (preferably mono or bicyclic) and may be aromatic or non-aromatic. Examples of aromatic groups that may be so formed include benzene and naphthalene. Examples of non-aromatic groups that may be so formed include cyclopentane, cyclohexane, and cyclooctane.

[0189] Any of R9, R10, R11, R12, R13, R14, and R15together with the atoms to which they are attached may represent an optionally substituted cyclic group. Any of R9, R10, R11, R12, R13, R14, and R15not representing a cyclic group are independently selected from hydrogen, an alkyl group and an alkenyl group as described herein. Two, three, four, five, or six of R9, R10, R11, R12, R13, R14, and R15together with the atoms to which they are attached may represent an optionally substituted cyclic group. Suitably at least R9and R11, or R9and R13, or R9and R15, or R11and R13, or R11and R15, or R9, R11and R13, or R9, R11and R15togetherwith the atoms to which they are attached may represent an optionally substituted cyclic group. For the avoidance of doubt, when any of R9, R10, R11, R12, R13, and R14togetherwith the atoms to which they are attached represent an optionally substituted cyclic group, one or more of R9, R10, R11, R12, R13, and R14may contribute to one or more double bonds (for example, aromaticity) in the cyclic group. For example, R12and R14may together form a carbon-carbon double bond, which may form part of an aromatic cyclic group.

[0190] The optionally substituted cyclic group represented by R5and R6, or R7and R8, or any of R9, R10, R11, R12, R13, R14, and R15, together with the atoms to which they are attached (when present) may be optionally substituted with any suitable substituent(s), such as for example one or more substituents independently selected from alkyl (for example C1-30, preferably C1-24, such as C1-4 or CS-24, alkyl), alkenyl (for example C2-30, preferably C2-24, such as C2-4 or Cs-24, alkenyl), alkoxy (for example C1-30, preferably C1-24, such as C1-4 or Cs-24, alkoxy), alkenyloxy (for example C2-30, preferably C2-24, such as C2-4 or Cs-24, alkenyloxy), carboxy, alkoxy-carbonyl (for example C1-30, preferably C1-24, such as C1-4 or Cs-24, alkoxy-carbonyl), alkenyloxy-carbonyl (for example C2-30, preferably C2-24, such as C2-4 or Cs-24, alkenyloxy-carbonyl), hydroxy, halo (for example chloro or fluoro), nitro and cyano groups. The optionally substituted cyclic group represented by R5and R6, or R7and R8, or any of R9, R10, R11, R12, R13, R14, and R15, together with the atoms to which they are attached (when present) may alternatively be substituted by groups which form a further cyclic anhydride group. An example of such a cyclic anhydride is pyromellitic dianhydride. However, in some embodiments the cyclic anhydride monomers of the formula (III), (IV) or (V) contain a single (i.e. only one) anhydride group. In such embodiments, the optionally substituted cyclic group represented by R5and R6, or R7and R8, or R9, R10, R11, R12, R13, and R14, together with the atoms to which they are attached (when present) may not be substituted by a further cyclic anhydride group.

[0191] Examples of suitable cyclic anhydrides of formula (III) in which R5and R6together with the carbon atoms to which they are attached represent an optionally substituted cyclic group include optionally substituted 1 ,2-cyclohexanedicarboxylic anhydride and 1 ,3-cyclopentanedicarboxylic anhydride. 1 ,2-Cyclohexanedicarboxylic anhydride is preferred.

[0192] Examples of suitable anhydrides of formula (IV) in which R7and R8together with the carbon atoms to which they are attached represent an optionally substituted cyclic group include optionally substituted phthalic anhydride, pyromellitic dianhydride, 1 ,2-naphthalic anhydride and 2,3-naphthalic anhydride. Examples of a substituted phthalic anhydride may include 1 ,2,4-benzenetricarboxylic anhydride, and 6-((octadec-9-en-1-yloxy)carbonyl)-1 ,3-dioxo-1 ,3-dihydroisobenzofuran-5-carboxylic acid.

[0193] Examples of suitable anhydrides of formula (V) in which any of R9, R10, R11, R12, R13, R14, and R15together with the carbon atoms to which they are attached represent an optionally substituted cyclic group include optionally substituted 1 ,8-naphthalic anhydride and homophthalic anhydride.

[0194] Preferred cyclic anhydrides include one or more cyclic anhydrides of formula (III) wherein R5and R6are each independently selected from hydrogen and a Cs-3o, such as a Cs-24, alkyl or alkenyl group, or wherein R5and R6together with the carbon atoms to which they are attached represent an optionally substituted cyclic group; or of formula (IV) wherein R7and R8are each independently selected from hydrogen and a Cs-3o, such as a Cs-24, alkyl or alkenyl group, or wherein R7and R8together with the carbon atoms to which they are attached represent an optionally substituted cyclic group; or of formula (V) wherein X is CR13R14, O, or S and R9, R10, R11, R12, R13, and R14are each independently selected from hydrogen and a Cs-3o, such as a Cs-24, an alkyl group or alkenyl group, and / or wherein any of R9, R10, R11, R12, R13, and R14together with the carbon atoms to which they are attached represent an optionally substituted cyclic group.

[0195] More preferred cyclic anhydrides include one or more cyclic anhydrides of formula (III) wherein R5and R6are each independently selected from hydrogen and a Cs-3o, such as a Cs-24, alkenyl group, or wherein R5and R6together with the carbon atoms to which they are attached represent an optionally substituted cyclic group; or of formula (IV) wherein R7and R8are both hydrogen, or wherein R7and R8together with the carbon atoms to which they are attached represent an optionally substituted cyclic group; or of formula (V) wherein X is CR13R14, O, or S and R9, R10, R11, R12, R13, and R14are each hydrogen, and / or wherein any of R9, R10, R11, R12, R13, and R14together with the carbon atoms to which they are attached represent an optionally substituted cyclic group.

[0196] At least one of the second monomers may be a cyclic anhydride of formula (III), (IV) or (V) wherein at least one of R5and R6, or at least one of R7and R8, or at least one of R9, R10, R11, R12, R13, R14, and R15, is a Ce-3o, such as a Cs-24, alkyl or alkenyl (more preferably alkenyl) group (such as an alkenyl group derived from a terminal olefin or an internal olefin, preferably an internal olefin). Preferably, at least one of the second monomers may be a cyclic anhydride of formula (III), (IV) or (V) wherein at least one of R5and R6, or at least one of R7and R8, or at least one of R9, R10, R11, R12, R13, R14, and R15, is a Cs-3o, such as a Cs-24, alkyl or alkenyl (more preferably alkenyl) group (such as an alkenyl group derived from a terminal olefin or an internal olefin, preferably an internal olefin) and the other (or others) is (or are) hydrogen.

[0197] For example, the cyclic anhydride may be an anhydride of formula (III) wherein R5and R6are both hydrogen (i.e. the cyclic anhydride may be succinic anhydride).

[0198] For example, the cyclic anhydride may be an anhydride of formula (IV) wherein R7and R8are both hydrogen (i.e. the cyclic anhydride may be maleic anhydride).

[0199] For example, the cyclic anhydride may be an anhydride of formula (V) in which X is CR13R14and R9, R10, R11, R12, R13, and R14each represent hydrogen (i.e. the cyclic anhydride may be glutaric anhydride). For example, the cyclic anhydride may be an anhydride of formula (V) in which X is O and R9, R10, R11, and R12each represent hydrogen (i.e. the cyclic anhydride may be diglycolic anhydride).

[0200] For example, the cyclic anhydride may be an anhydride of formula (V) in which X is S and R9, R10, R11, and R12each represent hydrogen (i.e. the cyclic anhydride may be thiodiglycolic anhydride).

[0201] For example, the or each cyclic anhydride may be an anhydride of formula (III) wherein R5and R6are both hydrogen or wherein one of R5and R6is an alkyl or alkenyl group (such as an alkenyl group derived from a terminal olefin or an internal olefin, preferably an internal olefin) and the other of R5and R6is hydrogen. For example, the or each cyclic anhydride may be an anhydride of formula (III) wherein R5and R6are both hydrogen or wherein one of R5and R6is a Ce-3o, such as a CS-24, alkyl or alkenyl (more preferably alkenyl) group (such as an alkenyl group derived from a terminal olefin or an internal olefin, preferably an internal olefin) and the other of R5and R6is hydrogen. Examples of such cyclic anhydride compounds include succinic anhydride, C20-24 alkenyl succinic anhydride, dodecenyl succinic anhydride (such as (2-dodecen-1-yl)succinic anhydride), nonenyl succinic anhydride, octadecenyl succinic anhydride and octenyl succinic anhydride.

[0202] Preferably, the or each cyclic anhydride may be an anhydride of formula (III) wherein one of R5and R6is an alkenyl group, such as a Ce-3o (preferably C8-24) alkenyl group (such as a Ce-3o (preferably C8-24) alkenyl group derived from a terminal olefin or an internal olefin, preferably an internal olefin), and the other of R5and R6is hydrogen. Examples of such cyclic anhydride compounds include C20-24 alkenyl succinic anhydride, dodecenyl succinic anhydride (such as (2-dodecen-1-yl)succinic anhydride), nonenyl succinic anhydride, octadecenyl succinic anhydride and octenyl succinic anhydride.

[0203] Preferably, the cyclic anhydride may be dodecenyl succinic anhydride, such as (2-dodecen-1-yl)succinic anhydride.

[0204] Preferably, the cyclic anhydride may be octadecenyl succinic anhydride.

[0205] The or each cyclic anhydride may be an anhydride of formula (III) wherein one of R5and R6is hydrogen and the other of R5and R6is a polyisobutenyl group, for example wherein the polyisobutenyl group suitably has a number average molecular weight of from 100 to 2000, preferably from 100 to 1000, for example 260 or 550. Preferably, the or each cyclic anhydride may be a cyclic anhydride of formula (III) or (IV) wherein R5and R6, or R7and R8, together with the carbon atoms to which they are attached represent an optionally substituted cyclic group, wherein the cyclic group is an aromatic or a non-aromatic group and is mono or polycyclic.

[0206] Preferably, the or each cyclic anhydride may be an anhydride of formula (III) wherein R5and R6together with the carbon atoms to which they are attached represent an optionally substituted cyclic group, wherein the cyclic group is a non-aromatic (for example saturated) mono or bicyclic group. More preferably, the or each cyclic anhydride may be a cyclic anhydride of formula (III) wherein R5and R6together with the carbon atoms to which they are attached represent an optionally substituted cyclic group, wherein the cyclic group is a non-aromatic (for example saturated) monocyclic group, such as a cyclohexane group.

[0207] Preferably, the or each cyclic anhydride may be an anhydride of formula (IV) wherein R7and R8together with the carbon atoms to which they are attached represent an optionally substituted cyclic group, wherein the cyclic group is an aromatic mono or bicyclic group, such as a benzene or naphthalene group. More preferably, the or each cyclic anhydride may be a cyclic anhydride of formula (IV) wherein R7and R8together with the carbon atoms to which they are attached represent an optionally substituted cyclic group, wherein the cyclic group is an aromatic monocyclic group, such as a benzene group.

[0208] Preferably, the or each cyclic anhydride may be an anhydride of formula (V) wherein X is CR13R14and R9, R10, R11, R12, R13, and R14together with the carbon atoms to which they are attached represent an optionally substituted cyclic group, wherein the cyclic group is an aromatic bicyclic group, such as a naphthalene group; or R11and R12are hydrogen and R9, R10, R13and R14together with the carbon atoms to which they are attached represent an optionally substituted cyclic group, wherein the cyclic group is an aromatic monocyclic group, such as a benzene group. More preferably, the or each cyclic anhydride may be an anhydride of formula (V) wherein X is CR13R14and R9, R10, R11, R12, R13, and R14together with the carbon atoms to which they are attached represent an optionally substituted cyclic group, wherein the cyclic group is an aromatic bicyclic group, such as a naphthalene group.

[0209] When the cyclic anhydride is an anhydride of formula (III) wherein R5and R6together with the carbon atoms to which they are attached represent an optionally substituted cyclohexane group, the cyclic anhydride may be of the formula (I HA):

[0210]

[0211] wherein n5 is an integer from 0 to 4 and each R16(when present) is independently selected from alkyl (for example C1-30, preferably C1-24, such as C1-4, alkyl), alkenyl (for example C2-30, preferably C2-24, such as C2-4, alkenyl), alkoxy (for example C1-30, preferably C1-24, such as C1-4, alkoxy), alkenyloxy (for example C2-30, preferably C2-24, such as C2-4, alkenyloxy), carboxy, alkoxy-carbonyl (for example C1-30, preferably C1-24, such as C1-4, alkoxy-carbonyl), alkenyloxycarbonyl (for example C2-30, preferably C2-24, such as C2-4, alkenyloxy-carbonyl), hydroxy, halo (for example chloro or fluoro), nitro and cyano groups, or when n5 is 2 the two R16groups may represent a further cyclic anhydride group (such as a further succinic anhydride group). In some embodiments, the cyclic anhydride of formula (IIIA) contains a single (i.e. only one) anhydride group. In such embodiments, two R16groups may not represent a further cyclic anhydride group. Examples of suitable succinic anhydrides of formula (IIIA) include 1 ,2-cyclohexanedicarboxylic anhydride.

[0212] When the cyclic anhydride is an anhydride of formula (IV) wherein R7and R8together with the carbon atoms to which they are attached represent an optionally substituted benzene group, the cyclic anhydride may be of the formula (IVA):

[0213]

[0214] wherein n6 is an integer from 0 to 4 and each R17(when present) is independently selected from alkyl (for example C1-30, preferably C1-24, such as C1-4, alkyl), alkenyl (for example C2-30, preferably C2-24, such as C2-4, alkenyl), alkoxy (for example C1-30, preferably C1-24, such as C1-4, alkoxy), alkenyloxy (for example C2-30, preferably C2-24, such as C2-4, alkenyloxy), carboxy, alkoxy-carbonyl (for example C1-30, preferably C1-24, such as C1-4, alkoxy-carbonyl), alkenyloxycarbonyl (for example C2-30, preferably C2-24, such as C2-4, alkenyloxy-carbonyl), hydroxy, halo (for example chloro or fluoro), nitro and cyano groups, or when n6 is 2 the two R17groups may represent a further cyclic anhydride group (such as a further succinic anhydride group).

[0215] When R17represents a alkoxy-carbonyl (for example C1-30, preferably Cs-24, alkoxy-carbonyl) or alkenyloxy-carbonyl (for example C2-30, preferably Cs-24, alkenyloxy-carbonyl), substituent, the alkoxy-carbonyl or alkenyloxy-carbonyl group may be of the formula -C(O)OR17’ wherein R17’ is a C1-30, preferably Cs-24, alkyl group or a C2-30, preferably Cs-24, alkenyl group. Suitably R17’ may represent an oleyl group.

[0216] Examples of suitable succinic anhydrides of formula (IVA) include phthalic anhydride, pyromellitic dianhydride, 1 ,2,4-benzenetricarboxylic anhydride, 1 ,2-naphthalic anhydride and 2,3-naphthalic anhydride, and 6-((octadec-9-en-1-yloxy)carbonyl)-1 ,3-dioxo-1 ,3-dihydroisobenzofuran-5-carboxylic acid.

[0217] When the cyclic anhydride is an anhydride of formula (V) wherein X is CR13R14and R9, R10, R11, R12, R13, and R14together with the carbon atoms to which they are attached represent an optionally substituted naphthalene group, the cyclic anhydride may be of the formula (VA):

[0218]

[0219] wherein each of m and m’ is independently an integer from 0 to 3 and each of R18and R19(when present) is independently selected from alkyl (for example C1-30, preferably C1-24, such as C1-4, alkyl), alkenyl (for example C2-30, preferably C2-24, such as C2-4, alkenyl), alkoxy (for example Ci-30, preferably C1-24, such as C1-4, alkoxy), alkenyloxy (for example C2-30, preferably C2-24, such as C2-4, alkenyloxy), carboxy, alkoxy-carbonyl (for example C1-30, preferably C1-24, such as C1-4, alkoxy-carbonyl), alkenyloxy-carbonyl (for example C2-30, preferably C2-24, such as C2-4, alkenyloxy-carbonyl), hydroxy, halo (for example chloro or fluoro), nitro and cyano groups.

[0220] Examples of suitable succinic anhydrides of formula (VA) include 1 ,8-naphthalic anhydride.

[0221] When the cyclic anhydride is an anhydride of formula (V) wherein X is CR13R14, R11and R12are hydrogen and R9, R10, R13and R14together with the carbon atoms to which they are attached represent an optionally substituted benzene group, the cyclic anhydride may be of the formula (VB):

[0222]

[0223] wherein m” is an integer from 0 to 4 and each R20(when present) is independently selected from alkyl (for example C1-30, preferably C1-24, such as C1-4, alkyl), alkenyl (for example C2-30, preferably C2-24, such as C2-4, alkenyl), alkoxy (for example C1-30, preferably C1-24, such as C1-4, alkoxy), alkenyloxy (for example C2-30, preferably C2-24, such as C2-4, alkenyloxy), carboxy, alkoxy-carbonyl (for example C1-30, preferably C1-24, such as C1-4, alkoxy-carbonyl), alkenyloxycarbonyl (for example C2-30, preferably C2-24, such as C2-4, alkenyloxy-carbonyl), hydroxy, halo (for example chloro or fluoro), nitro and cyano groups.

[0224] Examples of suitable succinic anhydrides of formula (VB) include homophthalic anhydride.

[0225] Suitably, the or each cyclic anhydride may be selected from one or more of succinic anhydride, maleic anhydride, glutaric anhydride, a Ce-3o alkenyl succinic anhydride such as C20-24 alkenyl succinic anhydride, dodecenyl succinic anhydride (such as (2-dodecen-1-yl)succinic anhydride), nonenyl succinic anhydride, octadecenyl succinic anhydride, octenyl succinic anhydride, octadecyl succinic anhydride, or octyl succinic anhydride, a branched alkenyl succinic anhydride such as tetrapropenyl succinic anhydride or polyisobutenyl succinic anhydride, phthalic anhydride, pyromellitic dianhydride, 1 ,2,4-benzenetricarboxylic anhydride, 1 ,2-cyclohexanedicarboxylic anhydride, 1 ,2-naphthalic anhydride, 2,3-naphthalic anhydride, 1 ,8-naphthalic anhydride and homophthalic anhydride.

[0226] Suitably, the or each cyclic anhydride may be selected from one or more of succinic anhydride, maleic anhydride, glutaric anhydride, a Ce-3o alkenyl succinic anhydride such as C20-24 alkenyl succinic anhydride, dodecenyl succinic anhydride (such as (2-dodecen-1-yl)succinic anhydride), nonenyl succinic anhydride, octadecenyl succinic anhydride, octenyl succinic anhydride, octadecyl succinic anhydride, or octyl succinic anhydride, and a branched alkenyl succinic anhydride such as tetrapropenyl succinic anhydride or polyisobutenyl succinic anhydride.

[0227] Suitably, the or each cyclic anhydride may be selected from one or more of phthalic anhydride, pyromellitic dianhydride, 1 ,2,4-benzenetricarboxylic anhydride, 1 ,2-cyclohexanedicarboxylic anhydride, 1 ,2-naphthalic anhydride, 2,3-naphthalic anhydride, 1 ,8-naphthalic anhydride and homophthalic anhydride.

[0228] More suitably, the or each cyclic anhydride may be selected from one or more of succinic anhydride, maleic anhydride, C20-24 alkenyl succinic anhydride, dodecenyl succinic anhydride (such as (2-dodecen-1-yl)succinic anhydride), nonenyl succinic anhydride, octadecenyl succinic anhydride, octenyl succinic anhydride, phthalic anhydride, pyromellitic dianhydride, 1 ,2,4-benzenetricarboxylic anhydride, 1 ,2-cyclohexanedicarboxylic anhydride, 1 ,2-naphthalic anhydride, 2,3-naphthalic anhydride, 1 ,8-naphthalic anhydride, homophthalic anhydride and glutaric anhydride.

[0229] More suitably, the or each cyclic anhydride may be selected from one or more of succinic anhydride, maleic anhydride, C20-24 alkenyl succinic anhydride, dodecenyl succinic anhydride (such as (2-dodecen-1-yl)succinic anhydride), nonenyl succinic anhydride, octadecenyl succinic anhydride, octenyl succinic anhydride, and glutaric anhydride.

[0230] Preferably, the or each cyclic anhydride may be selected from one or more of succinic anhydride, maleic anhydride, C 20-24 alkenyl succinic anhydride, dodecenyl succinic anhydride (such as (2-dodecen-1-yl)succinic anhydride), nonenyl succinic anhydride, octadecenyl succinic anhydride, octenyl succinic anhydride, phthalic anhydride, pyromellitic dianhydride, 1 ,2,4-benzenetricarboxylic anhydride, 1 ,2-cyclohexanedicarboxylic anhydride and 1 ,8-naphthalic anhydride.

[0231] Preferably, the or each cyclic anhydride may be selected from one or more of succinic anhydride, maleic anhydride, C 20-24 alkenyl succinic anhydride, dodecenyl succinic anhydride (such as (2-dodecen-1-yl)succinic anhydride), nonenyl succinic anhydride, octadecenyl succinic anhydride, and octenyl succinic anhydride.

[0232] Preferably, the or each cyclic anhydride may be selected from one or more of phthalic anhydride, pyromellitic dianhydride, 1 ,2,4-benzenetricarboxylic anhydride, 1 ,2-cyclohexanedicarboxylic anhydride and 1 ,8-naphthalic anhydride.

[0233] The cyclic anhydride compounds discussed herein may be commercially available or may be prepared using procedures well known in the art.

[0234] For example, alkenyl substituted succinic anhydrides are typically prepared by the reaction of an alkene with maleic anhydride. Preferably, the or each cyclic anhydride may be independently selected from a Ce-3o alkyl or alkenyl substituted succinic anhydride, phthalic anhydride and pyromellitic dianhydride.

[0235] Preferably, the or each cyclic anhydride may be independently selected from a Ce-3o alkyl or alkenyl substituted succinic anhydride.

[0236] Preferably, the or each cyclic anhydride may be independently selected from (2-dodecen-1-yl)succinic anhydride, nonenyl succinic anhydride, octadecenyl succinic anhydride, phthalic anhydride and pyromellitic dianhydride.

[0237] Preferably, the or each cyclic anhydride may be independently selected from (2-dodecen-1-yl)succinic anhydride, nonenyl succinic anhydride, and octadecenyl succinic anhydride.

[0238] Preferably, the or each cyclic anhydride may be independently selected from phthalic anhydride and pyromellitic dianhydride.

[0239] One or more of the second monomers may be a polyol.

[0240] The term polyol is used to refer to any compound including two or more hydroxy (OH) functional groups. In some embodiments the or each polyol may comprise carbon, hydrogen and oxygen atoms, and optionally additionally nitrogen atoms. In other embodiments, the or each polyol may consist essentially of or consist of carbon, hydrogen and oxygen atoms.

[0241] Suitable polyols for preparing the polymer may be compounds having from 2 to 10, preferably from 2 to 6, more preferably 2 or 3, most preferably 2, hydroxy groups.

[0242] Suitable polyols may include one or more of a polyol of formula (VI):

[0243] H-(OR21)P-OH

[0244] (VI)

[0245] wherein each R21is independently an optionally substituted hydrocarbylene group and p is an integer of at least 1. When p is an integer of greater than 1 , the polyol of formula (VI) may comprise groups R21that are all the same or may comprise groups R21that are different. Suitably, each R21in the formula (VI) may be the same. Preferably p is an integer from 1 to 140, such as from 1 to 110, from 1 to 40 or from 1 to 10.

[0246] For example, suitable polyols may include one or more of a polyol of formula (VIA): H-(OR22)q-OH

[0247] (VIA)

[0248] wherein each R22is independently an optionally substituted alkylene group and q is an integer of at least 1. When q is an integer of greater than 1 , the polyol of formula (VIA) may comprise groups R22that are all the same or may comprise groups R22that are different. Suitably, each R22in the formula (VIA) is the same. Preferably q is an integer from 1 to 140, such as from 1 to 110, from 1 to 40 or from 1 to 10.

[0249] When the polyol of formula (VI) or (VIA) contains a substituted hydrocarbylene or alkylene group, any suitable substituent may be present, such as for example a carboxy or amido substituent.

[0250] The polyol of formula (VIA) may have more than 2 hydroxy groups and the group R22may be a hydroxy substituted alkylene group. Each hydroxy substituted alkylene group R22may have 1 , 2 or more hydroxy groups. Each hydroxy substituted alkylene group R22may preferably have 1 hydroxy group.

[0251] The polyol of formula (VIA) may have 2 hydroxy groups and the group R22may be an optionally substituted alkylene group wherein the optional substituent is not hydroxy.

[0252] The polyol of formula (VI) or of formula (VIA) may be a sugar derived compound in which R21or R22includes one or more hydroxy residues.

[0253] The or each R21or R22may represent a cyclic alkylene unit. One or more heteroatoms (for example oxygen atoms) may be present in the cyclic alkylene unit. For example the unit may contain an ether linkage.

[0254] Suitably the or each R21or R22may be one or more saccharide units or may be substituted with one or more saccharide units.

[0255] Suitably the or each R21or R22may be an unsubstituted alkylene group.

[0256] Preferably the or each R21or R22is an optionally substituted alkylene group having from 1 to 50, such as from 1 to 40, preferably from 1 to 30, more preferably from 1 to 20, suitably from 1 to 12 or from 1 to 10, for example from 2 to 6, carbon atoms.

[0257] Preferably the or each R21or R22is an unsubstituted alkylene group having from 1 to 50, preferably from 1 to 20, more preferably from 1 to 12 or from 1 to 10, suitably from 2 to 6 carbon atoms. Each R21or R22may be straight chained or branched. Suitably the or each R21or R22may be an ethylene, propylene, butylene, pentylene, hexylene or dodecylene group. When R21or R22has more than 2 carbon atoms any isomer may be present. Preferably R21or R22is an ethylene or a propylene group, most preferably an ethylene group.

[0258] When q is 1 , R22may be a group of formula (CH2)x wherein x is from 2 to 12, preferably from 3 to 12.

[0259] Suitably when q is 1 , R22may be a straight chain or branched optionally substituted alkylene group and the polyol may be selected from ethylene glycol, propylene glycol, 1 ,3-propanediol, 1.2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,6-hexanediol, 1 ,12-dodecanediol, trimethylolpropane, 2-ethyl-1 ,3, -hexanediol, 2, 2-diethyl-1 ,3-propanediol, 2,2-bis(hydroxymethyl)propionic acid, pentaerythritol, sorbitol, xylitol, glycerol and neopentyl glycol.

[0260] Suitably when q is 1 , R22may be a straight chain or branched alkylene group having from 2 to 12, preferably from 3 to 12, carbon atoms. Suitable compounds of this type include ethylene glycol, propylene glycol, 1 ,3-propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,6-hexanediol, 1 ,12-dodecanediol, trimethylolpropane, 2-ethyl-1 ,3, -hexanediol, 2,2-diethyl-1 ,3-propanediol, pentaerythritol and neopentyl glycol.

[0261] Suitably when q is 1 , R22may be a branched alkylene group having from 2 to 12, preferably from 3 to 12, carbon atoms. Suitable compounds of this type include propylene glycol, 1 ,2-butanediol, 1.3-butanediol, trimethylolpropane, 2-ethyl-1 ,3, -hexanediol, 2, 2-diethyl-1 ,3-propanediol, pentaerythritol and neopentyl glycol. 1 ,6-hexanediol is a preferred polyol.

[0262] Suitably when q is 2 or more, the or each R22may be a straight chain or branched alkylene group and the polyol may, for example, be selected from diglycerol, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, polyethylene glycol and polypropylene glycol.

[0263] Suitably when q is 2 or more, the or each R22may be a straight chain or branched alkylene group having from 2 to 4, preferably 2 or 3, carbon atoms. Suitable compounds of this type include diethylene glycol, triethylene glycol, di propylene glycol, tripropylene glycol, polyethylene glycol (PEG), for example having a molecular weight of from 150 to 6000, and polypropylene glycol (PPG), for example having a molecular weight of from 400 to 2000. Preferred compounds of this type include polyethylene glycol (PEG), for example having a molecular weight of from 150 to 6000, and polypropylene glycol (PPG), for example having a molecular weight of from 400 to 2000 (especially PPG). Suitable polyols may include one or more of PEG 6000, PEG 1500, PEG 1000, PEG 600, PEG 400, PEG 200, PPG 2000, PPG 1000 and PPG 425. The or each R21or R22may comprise a mixture of isomers. For example when R21or R22is propylene, the polyol may include moieties -CH2CH(CH3)- and -CH(CH3)CH2- in any orderwithin the chain.

[0264] R21or R22may comprise a mixture of different groups for example ethylene, propylene or butylene units.

[0265] The or each R22may be an ethylene, propylene or butylene group. For example, the or each R22may be an n-propylene or n-butylene group or an isopropylene or isobutylene group. For example the or each R22may be -CH2CH2-, -CH2CH(CH3)-, - CH(CH3)CH2-, CH2CH2CH2-, -CH2C(CH3)2-, -CH2CH2CH2CH2-, -CH(CH3)CH(CH3)- or-CH2CH(CH2CH3)-.

[0266] Preferably R22is selected from -CH2CH2-, -CH2CH2CH2-, -CH(CH3)CH2- or -CH2CH(OH)CH2, more preferably from -CH2CH2-, and-CFhCF CF -.

[0267] Suitably the polyol of formula (VI) or (VIA) may be a sugar derived alcohol, for example, glucose, fructose, trehalose, sucrose, lactose, maltose or sorbitol, preferably sorbitol.

[0268] Suitably the polyol of formula (VI) may be selected from one or more of 1 ,12-dodecanediol, 1 ,6-hexanediol, trimethylolpropane, neopentyl glycol, polyethylene glycol (such as PEG 6000, PEG 1500, PEG 1000, PEG 600, PEG 400, PEG 200), polypropylene glycol (such as PPG 2000, PPG 1000, PPG 425), sorbitol, trimethylolpropane and xylitol.

[0269] Suitably, the polyol, for example of formula (VI), may be an ester of glycerol (also known as a glyceride) and a hydroxycarboxylic acid. The ester of glycerol may be a mono-, di- or triglyceride, suitably a tri-glyceride. Suitably, the hydroxycarboxylic acid comprises one or more hydroxyl groups and one or more carboxylic acid groups. The hydroxycarboxylic acid may be a monocarboxylic acid comprising one or more hydroxyl groups.

[0270] The hydroxycarboxylic acid may be of the formula R23COOH, wherein R23is a hydroxylsubstituted hydrocarbyl group. R23is suitably a hydroxy-substituted alkyl, alkenyl or alkaryl group, preferably a hydroxy-substituted alkyl or alkenyl group. R23suitably comprises from 1 to 25 carbon atoms, preferably from 1 to 20 carbon atoms, more preferably from 1 to 17 carbon atoms.

[0271] Suitably, the hydroxycarboxylic acid may be selected from glycolic acid, lactic acid, hydroxy butyric acid, hydroxyvaleric acid, hydroxycaproic acid, hydroxystearic acid (preferably 12-hydroxystearic acid), 2,2-bis(hydroxymethyl)propionic acid, mandelic acid or ricinoleic acid. Preferably, the hydroxycarboxylic acid or the cyclic ester thereof may be selected from glycolic acid, mandelic acid, ricinoleic acid, malic acid, tartaric acid or citric acid. More preferably, the hydroxycarboxylic acid or the cyclic ester thereof is ricinoleic acid.

[0272] Preferably, when the polyol is an ester of glycerol, the polyol may be a mono-, di- or tri-glyceride of ricinoleic acid. Most preferably, when the polyol is an ester of glycerol, the polyol may be a tri-glyceride of ricinoleic acid, such as castor oil.

[0273] Suitable polyols may include one or more of an alkoxylated polyol of formula (VI) or (VIA). These polyols may be the reaction product of a polyol of formula (VI) or (VIA) and one or more alkylene oxides, such as ethylene oxide or propylene oxide. Such alkoxylated polyols may include polyoxyethylene (80) sorbitan monooleate (also known as Tween® 80) and 2,4,7,9-tetramethyl-5-decyne-4,7-diol ethoxylate.

[0274] Preferably, the or each polyol may be independently selected from castor oil, 1 ,6-hexanediol, sorbitol, neopentyl glycol and a polyalkylene glycol (such as polyethylene glycol (PEG) or polypropylene glycol (PPG), for example PEG 200 or PPG 2000).

[0275] Preferably, the or each polyol may be independently selected from 1 ,6-hexanediol and a polyalkylene glycol (such as polyethylene glycol (PEG) or polypropylene glycol (PPG), for example PEG 200 or PPG 2000). More preferably, the or each polyol may be independently selected from 1 ,6-hexanediol and polypropylene glycol (PPG), for example PPG 2000).

[0276] Preferably, the or each polyol may be independently selected from castor oil, 1 ,6-hexanediol, sorbitol, neopentyl glycol and a polyalkylene glycol (such as PEG 200).

[0277] When the or each polyol comprises carbon, hydrogen, oxygen and nitrogen atoms, the or each polyol may comprise two or more (such as 2 or 3) hydroxy groups and one or more (suitably one) amine groups. The amine groups may suitably be secondary or tertiary amines. Preferably the amine groups are tertiary amines. These polyols may be referred to herein as nitrogen containing polyols.

[0278] For example, suitable nitrogen containing polyols may include one or more of a polyol of formula (VII) or a derivative thereof:

[0279] NR24R25R26(VII)

[0280] wherein R24, R25and R26are each independently selected from hydrogen, hydroxyalkyl and hydrocarbyl, provided that at least two of R24, R25and R26represents a hydroxyalkyl group. Preferably, the at least two of R24, R25and R26that represent a hydroxyalkyl group are the same. For example, in the compounds of formula (VII), R24and R25may each represent hydroxyalkyl and R26may represent hydrogen, hydroxyalkyl or hydrocarbyl.

[0281] In the formula (VII), the hydroxyalkyl group may contain from 1 to 8, such as from 1 to 4, such as 2 or 3, carbon atoms. For example, each hydroxyalkyl group may be hydroxyethyl or hydroxypropyl, particularly hydroxyethyl.

[0282] In the formula (VII), the hydrocarbyl group (when present) may represent any suitable such group, such as an alkyl group, for example an alkyl group containing from 1 to 10, such as from 1 to 6 or from 1 to 4, carbon atoms. Thus, the hydrocarbyl group may represent a methyl, ethyl, propyl or butyl group (especially butyl or methyl).

[0283] For example, in the compounds of formula (VII), R24and R25may each represent hydroxyalkyl and R26may represent hydrogen, hydroxyalkyl or hydrocarbyl (especially hydrogen or hydrocarbyl, more especially hydrocarbyl).

[0284] Preferably in the compounds of formula (VII), R24and R25both represent hydroxyethyl and R26represents hydrogen or hydrocarbyl, such as a hydrocarbyl group containing from 1 to 6, or from 1 to 4, carbon atoms. Preferably in the compounds of formula (VII), R24and R25both represent hydroxyethyl and R26represents hydrogen or an alkyl group containing from 1 to 6, or from 1 to 4, carbon atoms (especially methyl).

[0285] Examples of suitable nitrogen containing polyols include N-methyl diethanolamine, N-butyl diethanolamine, triethanolamine and diethanolamine, and derivatives thereof.

[0286] References herein to nitrogen containing polyols include derivatives thereof, such as a corresponding quaternary compound. Thus, as example of a suitable derivative of a nitrogen containing polyol is tris(2-hydroxyalkyl)methylammonium compound, for example tris(2-hydroxyethyl)methylammonium methylsulfate, which is a quaternary ammonium salt of triethanolamine.

[0287] Preferably, the or each nitrogen containing polyol may be independently selected from N-butyl diethanolamine, diethanolamine and N-methyl diethanolamine, and derivatives (for example quaternary ammonium salts) thereof.

[0288] Further examples of suitable nitrogen containing polyols include those formed by reaction of a hydroxy substituted cyclic ester or cyclic carbonate, such as glycerol carbonate or gluconolactone, with a suitable primary or secondary amine compound, such as ethanolamine, dipropylamine, hexylamine, dodecylamine, phenethylamine, dipropylamine, ethylenediamine, or a polyether polyamine. Suitable polyether amines may include polyether monoamines (such as for example Jeffamine M-1000) and polyether polyamines (such as for example Jeffamine ED-600). As the skilled person would appreciate, the reaction of a hydroxy substituted cyclic ester or cyclic carbonate with a suitable primary or secondary amine compound will result in a ring opening reaction to form a compound such as a N-carbamoyl polyol or an amido polyol.

[0289] The or each polyol may be selected from one or more polyol of the formula (VI) or (VIA) as defined herein (including an ester of glycerol and a hydroxycarboxylic acid (such as castor oil)), one or more of an alkoxylated polyol of formula (VI) or (VIA) as defined herein, one or more nitrogen containing polyol as defined herein (including compounds of the formula (VII)) and one or more polyol formed by reaction of a hydroxy substituted cyclic ester or cyclic carbonate with a suitable primary or secondary amine compound.

[0290] Preferably, the or each polyol may be selected from one or more polyol of the formula (VI) or (VIA) as defined herein (including an ester of glycerol and a hydroxycarboxylic acid (such as castor oil)), one or more of an alkoxylated polyol of formula (VI) or (VIA) as defined herein, one or more nitrogen containing polyol of the formula (VII) as defined herein and one or more polyol formed by reaction of a hydroxy substituted cyclic ester or cyclic carbonate with a suitable primary or secondary amine compound.

[0291] More preferably, the or each polyol may be selected from one or more polyol of the formula (VI) or (VIA) as defined herein (such as an ester of glycerol and a hydroxycarboxylic acid , for example castor oil), and one or more nitrogen containing polyol of the formula (VII) as defined herein.

[0292] In one embodiment, the or each polyol may be selected from one or more polyol of the formula (VI) or (VIA) as defined herein, such as an ester of glycerol and a hydroxycarboxylic acid (for example castor oil) /

[0293] In another embodiment, the or each polyol may be selected from one or more of an alkoxylated polyol of formula (VI) or (VIA) as defined herein.

[0294] In one embodiment, the or each polyol may be selected from one or more polyol of the formula (VI) or (VIA) as defined herein, such as an ester of glycerol and a hydroxycarboxylic acid (for example castor oil) and from one or more of an alkoxylated polyol of formula (VI) or (VIA) as defined herein. In another embodiment, the or each polyol may be selected from one or more nitrogen containing polyol as defined herein (including compounds of the formula (VII)).

[0295] In another embodiment, the or each polyol may be selected from one or more polyol formed by reaction of a hydroxy substituted cyclic ester or cyclic carbonate with a suitable primary or secondary amine compound.

[0296] One or more of the second monomers may be a polycarboxylic acid or a reactive equivalent thereof.

[0297] The polycarboxylic acid may comprise two or more carboxylic acid groups, such as two or three carboxylic acid groups. Preferred polycarboxylic acids are dicarboxylic acids.

[0298] The polycarboxylic acid may be aliphatic or aromatic. The aliphatic polycarboxylic acid may be cycloaliphatic. The aliphatic polycarboxylic acid may be saturated or unsaturated. By the term “unsaturated” we mean that the polycarboxylic acid comprises one or more carbon-carbon double bonds.

[0299] The polycarboxylic acid may comprise one or more heteroatoms other than the oxygen atoms in the carboxylic acid groups. By the term “heteroatoms” we mean atoms other than carbon or hydrogen, such as oxygen, nitrogen and sulfur atoms. For example, the polycarboxylic acid may comprise one or more moieties selected from hydroxy groups, amino groups, ether groups, and / or thioether groups.

[0300] The polycarboxylic acid may be of the formula HOOC(CR272)nyCOOH, wherein n7 is from 0 to 30; and

[0301] each R27is independently hydrogen or a substituent;

[0302] and / or two R27groups on the same carbon atom may be taken together to form a methylene (=CH2) group;

[0303] and / or when n7 is two or more, two R27groups on adjacent carbon atoms may be taken together to form a double bond.

[0304] n7 is suitably from 1 to 20, preferably from 2 to 16, more preferably from 2 to 12, for example from 2 to 10.

[0305] Each (C R272) group can be the same or different.

[0306] Unless otherwise specified, the terms “each R27”, “R27groups” and the like are intended to refer to all instances of the “R27” group in the formula HOOC(CR272)nyCOOH, Each R27may be hydrogen. Alternatively, one or two R27groups may be a substituent and the remaining R27groups may be hydrogen. Any suitable substituent may be used as R27. The substituent may be a hydrocarbyl group ora heteroatom-containing group. Examples of suitable substituents include hydroxy groups, amino groups, carboxyl groups, alkyl groups, alkenyl groups, aryl groups, aralkyl groups, and alkaryl groups, wherein the alkyl groups, alkenyl groups, aryl groups, aralkyl groups, and alkaryl groups are optionally substituted with one or more of a hydroxy group, an amino group, and / or a carboxyl group.

[0307] One or two of the R27groups may be a hydroxy group. Another of the R27groups may optionally be a carboxyl group or a carboxyl-substituted methyl group, and the remaining R27groups are suitably hydrogen. Suitably, one or two of the R27groups may be a hydroxy group, another of the R27groups may be a carboxyl group or a carboxyl-substituted methyl group, and the remaining R27groups may be hydrogen; or one ortwo of the R27groups may be a hydroxy group and the remaining R27groups may be hydrogen. The polycarboxylic acid may be malic acid, tartaric acid, or citric acid.

[0308] One ortwo R27groups may be an alkyl or alkenyl group. Preferably, one R27group is an alkyl or alkenyl group. The remaining R27groups are suitably hydrogen. Each alkyl or alkenyl group may contain from 6 to 30, such as from 8 to 24, carbon atoms. The polycarboxylic acid may be an alkyl or alkenyl substituted succinic acid, preferably an alkenyl substituted succinic acid. Examples of such polycarboxylic acids include C20-24 alkenyl succinic acid, dodecenyl succinic acid (such as (2-dodecen-1-yl)succinic acid), nonenyl succinic acid, octadecenyl succinic acid and octenyl succinic acid.

[0309] One R27group may be a polyisobutenyl group and the remaining R27groups may be hydrogen. The polyisobutenyl group suitably has a number average molecular weight of from 100 to 2000, preferably from 100 to 1000, for example 260 or 550. The polycarboxylic acid may be a polyisobutenyl succinic acid, for example wherein the polyisobutenyl group has a number average molecular weight of 260 or 550.

[0310] Two R27groups on the same carbon atom may be taken together to form a methylene (=CH2) group. The polycarboxylic acid may comprise one or more such methylene groups. Two R27groups on the same carbon atom may be taken together to form a methylene (=CH2) group and the remaining R27groups may be hydrogen. The polycarboxylic acid may be itaconic acid.

[0311] When n7 is 2 or more, two R27groups on adjacent carbon atoms may be taken together to form a double bond. The polycarboxylic acid may comprise one or more such double bonds. The double bond may be in a cis or trans configuration. Two R27groups on adjacent carbon atoms may be taken together to form a double bond and the remaining R27groups may be hydrogen. The polycarboxylic acid may be maleic acid or fumaric acid.

[0312] The polycarboxylic acid may be of the formula HOOC(CH2)nsCOOH, wherein n8 is from 0 to 30.

[0313] n8 is suitably from 1 to 20, preferably from 2 to 16, more preferably from 4 to 12, for example from 5 to 10.

[0314] The polycarboxylic acid may be selected from oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, or dodecanedioic acid.

[0315] Preferably, the polycarboxylic acid may be selected from pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, or dodecanedioic acid.

[0316] The polycarboxylic acid may be of the formula HOOC(CH2)miX(CH2)m2COOH, wherein m1+m2 is from 0 to 30 and X is O, S, or NR28wherein R28is hydrogen or a hydrocarbyl group.

[0317] ml +m2 is suitably from 1 to 20, preferably from 2 to 16, more preferably from 2 to 12, for example from 2 to 6.

[0318] ml and m2 may each independently be from 0 to 30, suitably from 1 to 19, preferably from 1 to 15, more preferably from 1 to 11 , for example from 1 to 5.

[0319] R28may be a hydrocarbyl group, such as an alkyl or alkenyl group. The hydrocarbyl group may contain from 1 to 12 carbon atoms, preferably from 1 to 6 carbon atoms. Preferably, R28is hydrogen.

[0320] X is preferably O or S.

[0321] The polycarboxylic acid may be selected from diglycolic acid, thiodiglycolic acid, 3,3’-thiodipropanoic acid, or iminodiacetic acid, preferably from diglycolic acid or thiodiglycolic acid. A preferred polycarboxylic acid is diglycolic acid.

[0322] The polycarboxylic acid may be of the formula HOOCCH2(OCH2CHR29)x2OCH2COOH, wherein x2 is from 1 to 30 and each R29is independently hydrogen or a hydrocarbyl group.

[0323] x2 is suitably from 1 to 20, preferably from 2 to 16, more preferably from 4 to 14, for example from 6 to 12, such as 10. Each R29may independently be a hydrocarbyl group, such as an alkyl group. The alkyl group may contain from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms. The alkyl group is preferably methyl. In some embodiments, a portion of R29groups are hydrocarbyl groups (such as methyl groups) and the remaining R29groups are hydrogen.

[0324] Preferably, each R29is hydrogen.

[0325] The polycarboxylic acid may be a polyethylene glycol)bis(carboxymethyl) ether. The polyethylene glycol)bis(carboxymethyl) ether may contain from 1 to 20 ethylene oxide units (i.e. -CH2CH2O-), preferably from 2 to 16 ethylene oxide units, more preferably from 4 to 14 ethylene oxide units, for example from 6 to 12 ethylene oxide units, such as 10 ethylene oxide units. The polycarboxylic acid may be a polyethylene glycol)bis(carboxymethyl) ether containing 10 ethylene oxide units.

[0326] The polycarboxylic acid may comprise a cyclic group. The cyclic group may be substituted, for example with alkyl or alkenyl groups. The carboxyl groups of the polycarboxylic acid may be attached directly to the cyclic group, or via an alkyl or alkenyl group.

[0327] The cyclic group may be a cycloaliphatic group. Examples of cycloaliphatic groups include cyclohexane and cyclohexene.

[0328] The polycarboxylic acid may be 1 ,2-cyclohexanedicarboxylic acid or 1 ,4-cyclohexanedicarboxylic acid.

[0329] The cyclic group may be an aromatic group. Examples of aromatic groups include benzene and naphthalene.

[0330] The polycarboxylic acid may be selected from phthalic acid, isophthalic acid, terephthalic acid, homophthalic acid, 1 ,2,4-benzenetricarboxylic acid, pyromellitic acid, 1 ,2-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid. 1 ,8-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, or 2,7-naphthalenedicarboxylic acid.

[0331] The polycarboxylic acid may be a dimer acid. Such compounds are formed from the dimerisation of unsaturated acids, for example unsaturated fatty acids having from 6 to 50, suitably from 8 to 40, preferably from 10 to 36, for example from 10 to 20 carbon atoms, or from 16 to 20 carbon atoms. The dimer acid may be hydrogenated or unhydrogenated. Preferably, the dimer acid is hydrogenated. The dimer acid may have from 12 to 100 carbon atoms, preferably from 16 to 72 carbon atoms such as from 20 to 40 carbon atoms, for example from 32 to 40 carbon atoms.

[0332] Preferred dimer acids comprise C36 dimer acids such as those prepared by dimerising oleic acid, linoleic acid and mixtures comprising oleic and linoleic acid, for example, tall oil fatty acids. Preferably, the dimer acid comprises a dimer acid prepared by dimerising oleic acid. The dimer acid may be a hydrogenated C36 dimer acid.

[0333] A reactive equivalent of the polycarboxylic acid may be used. By the term “reactive equivalent”, we mean a compound that results in the same reaction product as the corresponding polycarboxylic acid. Suitable reactive equivalents include acid chlorides and esters of the polycarboxylic acids described herein.

[0334] The reactive equivalent may be an acid chloride of the polycarboxylic acid. The acid chloride of the polycarboxylic acid suitably does not comprise any free carboxylic acid groups.

[0335] The reactive equivalent may be an ester of the polycarboxylic acid. The ester of the polycarboxylic acid suitably does not comprise any free carboxylic acid groups. The ester of the polycarboxylic acid is suitably a hydrocarbyl ester, such as an alkyl ester, an alkenyl ester, an aryl ester, an aralkyl ester, or an alkaryl ester. Preferably the ester is an alkyl ester. The alkyl ester is suitably formed by reacting the polycarboxylic acid with an alkanol. The alkanol suitably contains from 1 to 10 carbon atoms, such as from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms. The alkanol is preferably methanol. The alkyl ester is preferably a methyl ester.

[0336] Suitably, the or each polycarboxylic acid or the reactive equivalent thereof may be selected from oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid, C 20-24 alkenyl succinic acid, dodecenyl succinic acid (such as (2-dodecen-1-yl)succinic acid), nonenyl succinic acid, octadecenyl succinic acid, octenyl succinic acid, polyisobutenylsuccinic acid, itaconic acid, 1 ,2-cyclohexanedicarboxylic acid, 1 ,4-cyclohexanedicarboxylic acid, phthalic acid, isophthalic acid, terephthalic acid, homophthalic acid, 1 ,2,4-benzenetricarboxylic acid, pyromellitic acid, 1 ,2-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 1 ,8-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, diglycolic acid, thiodiglycolic acid, 3,3’-thiodipropanoic acid, iminodiacetic acid, polyethylene glycol)bis(carboxymethyl) ether, a dimer acid, or an acid chloride or ester thereof.

[0337] Suitably, the or each polycarboxylic acid or the reactive equivalent thereof may be selected from oxalic acid, succinic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, maleic acid, malic acid, tartaric acid, citric acid, 1 ,4-cyclohexanedicarboxylic acid, isophthalic acid, terephthalic acid, diglycolic acid, thiodiglycolic acid, polyethylene glycol)bis(carboxymethyl) ether, a hydrogenated dimer acid or an acid chloride thereof.

[0338] Suitably, the or each polycarboxylic acid or the reactive equivalent thereof may be selected from oxalic acid, succinic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, maleic acid, malic acid, tartaric acid, citric acid, 1 ,4-cyclohexanedicarboxylic acid, isophthalic acid, diglycolic acid, thiodiglycolic acid, polyethylene glycol)bis(carboxymethyl) ether, a hydrogenated dimer acid, or an acid chloride thereof.

[0339] Preferably, the or each polycarboxylic acid or the reactive equivalent thereof may be selected from succinic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, maleic acid, malic acid, tartaric acid, citric acid, 1 ,4-cyclohexanedicarboxylic acid, terephthalic acid, diglycolic acid, thiodiglycolic acid, polyethylene glycol)bis(carboxymethyl) ether, a hydrogenated dimer acid, oxalyl chloride, isophthaloyl chloride, or terephthaloyl chloride. Citric acid and diglycolic acid may be preferred polycarboxylic acids.

[0340] One or more of the second monomers may be a monocarboxylic acid or ester thereof;

[0341] Suitable monocarboxylic acids may be aliphatic or aromatic. The aliphatic monocarboxylic acid may be cycloaliphatic. The aliphatic monocarboxylic acid may be saturated or unsaturated. The monocarboxylic acid may contain from 2 to 40 carbon atoms, suitably from 4 to 30 carbon atoms, preferably from 6 to 20 carbon atoms, for example from 8 to 18 carbon atoms. The monocarboxylic acid may be a fatty acid.

[0342] Examples of suitable monocarboxylic acids or esters thereof include hexanoic acid, octanoic acid, decanoic acid, lauric acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, elaidic acid, linoleic acid, linolelaidic acid, arachidic acid, arachidonic acid, behenic acid, erucic acid, and esters (preferably methyl esters) thereof.

[0343] Preferably, the monocarboxylic acid is selected from propionic acid, hexanoic acid, lauric acid, stearic acid, oleic acid, or erucic acid.

[0344] One or more of the second monomers may be an epoxide compound.

[0345] Suitable epoxide compounds may comprise one or more than one epoxide group. For example, suitable epoxide compounds may comprise two epoxide groups. Preferred epoxide compounds comprise a single (i.e. only one) epoxide group. Examples of suitable epoxide compounds include 1 ,2-epoxydodecane, ethyl glycidyl ether, isopropylglycidyl ether, 2-ethylhexyl glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, butyl glycidyl ether (such as n-butyl glycidyl ether), 1 ,2-epoxyhexane, epichlorohydrin, glycidyltrimethylammonium chloride, cyclopentene oxide, cyclohexene oxide, polyethylene glycol) diglycidyl ether, polypropylene glycol) diglycidyl ether and poly(butylene glycol) diglycidyl ether.

[0346] One or more of the second monomers may be a polyfunctional monomer having a reactive amino group.

[0347] By the term “polyfunctional monomer” we mean a monomer with at least two reactive groups. By the term “reactive group” we mean a group that reacts with the first monomer and / or the second monomer. At least one of the reactive groups is a reactive amino group. The other reactive groups in the polyfunctional monomer may be reactive amino groups, or may be reactive groups other than amino groups, such as hydroxy groups or carboxyl groups. Reactive amino groups are suitably primary amino groups or secondary amino groups.

[0348] The polyfunctional monomer may comprise at least one reactive amino group and at least one hydroxy group. The polyfunctional monomer may be an alkanolamine or an alkoxylated alkanolamine. The polyfunctional monomer may comprise at least two reactive amino groups. The polyfunctional monomer may be an aliphatic diamine, a polyether diamine, or a polyalkylene polyamine. The polyfunctional monomer may comprise at least one reactive amino group and at least one carboxyl group. The polyfunctional monomer may be an amino acid, such as a naturally occurring amino acid.

[0349] Examples of suitable polyfunctional monomers having at least one reactive amino group include ethanolamine, diethanolamine, ethylene diamine, coco propylene diamine, diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), a polyether diamine (preferably Jeffamine ED-600, Jeffamine ED-900, or Jeffamine ED-2003 which are commercially available), alanine, arginine, asparagine, aspartate, cysteine, glutamine, glutamate, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, and valine.

[0350] One or more of the second monomers may be a monoalcohol

[0351] Suitable monoalcohols may be aliphatic or aromatic. The aliphatic monoalcohol may be cycloaliphatic. The aliphatic monoalcohol may be saturated or unsaturated. The monoalcohol may contain from 2 to 40 carbon atoms, suitably from 4 to 30 carbon atoms, preferably from 6 to 20 carbon atoms, for example from 8 to 18 carbon atoms. The monoalcohol may be a fatty alcohol.

[0352] Examples of suitable monoalcohols include hexanol, octanol, 2-ethylhexanol, decanol, dodecanol alcohol, myristyl alcohol, myristoleyl alcohol, palmityl alcohol, palmitoleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, linoleyl alcohol, linolelaidyl alcohol, arachidyl alcohol, arachidonyl alcohol, behenyl alcohol, erucyl alcohol, benzyl alcohol, glycerol carbonate and choline chloride.

[0353] Preferably, the monoalcohol is glycerol carbonate, hexanol or oleyl alcohol.

[0354] Preferably, the monoalcohol is hexanol or oleyl alcohol.

[0355] Glycerol carbonate is a preferred monoalcohol.

[0356] One or more of the second monomers may be a monofunctional monomer having a reactive amino group.

[0357] Suitable monofunctional monomers having a reactive amino group have one reactive amino group and no other reactive groups. The monofunctional monomer may contain other functional groups that are not reactive groups, such as tertiary amino groups or ether groups. The monofunctional monomer may be an aliphatic monoamine (such as a fatty alkyl amine), an N,N-dialkylaminoalkylamine, or a polyether monoamine.

[0358] The polyether monoamine suitably comprises a polyether backbone selected from polyethylene glycol (PEG), polypropylene glycol (PPG), or a copolymer of polyethylene glycol (PEG) and polypropylene glycol (PPG). The copolymer of PEG and PPG may be a block copolymer or a random copolymer. The polyether backbone is suitably capped at one end with the reactive amino group, and capped at the other end with an alkyl group (preferably a methyl group). The polyether monoamine suitably has a molecular weight of from 150 to 6000, preferably from 400 to 3000, for example from 600 to 2000. The polyether monoamine may have a weight average molecular weight of from 150 to 6000, preferably from 400 to 3000, for example from 600 to 2000.

[0359] Examples of suitable monofunctional monomers having a reactive amino group include propylamine, dipropylamine, butylamine, hexylamine, octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, tallow alkyl amine, benzylamine, phenethylamine, 3-dimethylaminopropylamine (DMAPA), or Jeffamine M-1000 (which is commercially available). Preferably, the monofunctional monomer having a reactive amino group is selected from dodecylamine, N,N-dimethylaminopropylamine (DMAPA), or Jeffamine M-1000.

[0360] In one embodiment, the polymer may be the reaction product of monomers comprising one (i.e. a single) hydroxycarboxylic acid or a cyclic ester thereof and one (i.e. a single) monomer (i) to (viii) as defined herein. In other embodiments, the polymer may be the reaction product of monomers comprising two different hydroxycarboxylic acids or cyclic esters thereof and one (i.e. a single) monomer (i) to (viii) as defined herein, or the polymer may be the reaction product of monomers comprising one (i.e. a single) hydroxycarboxylic acid or a cyclic ester thereof and two different monomers (i) to (viii) as defined herein.

[0361] The combined amount of the one or more first monomers and the one or more second monomers (when present) may be at least 50 mol%, suitably at least 75 mol%, preferably at least 90 mol%, for example at least 95 wt% of the monomers that are reacted to obtain the polymer.

[0362] In one embodiment, the polymer may be the reaction product of monomers consisting essentially of or consisting of one (i.e. a single) hydroxycarboxylic acid ora cyclic ester thereof and one (i.e. a single) monomer (i) to (viii) as defined herein. In other embodiments, the polymer may be the reaction product of monomers consisting essentially of or consisting of two different hydroxycarboxylic acids or cyclic esters thereof and one (i.e. a single) monomer (i) to (viii) as defined herein, or the polymer may be the reaction product of monomers consisting essentially of or consisting of one (i.e. a single) hydroxycarboxylic acid or a cyclic ester thereof and two different monomers (i) to (viii) as defined herein.

[0363] The polymer for use herein may be the reaction product of monomers comprising the one or more first monomers and optionally one or more second monomers as disclosed herein. In other words, the polymer may be the reaction product of monomers comprising one or more first monomers as disclosed herein and optionally one or more second monomers as disclosed herein.

[0364] The polymer for use herein may be the reaction product of monomers consisting essentially of or consisting of the one or more first monomers and optionally one or more second monomers as disclosed herein. In other words, the polymer may be the reaction product of monomers consisting essentially of or consisting one or more first monomers as disclosed herein and optionally one or more second monomers as disclosed herein. The polymer for use herein is suitably the reaction product of no more than four different monomers. Preferably, the polymer is the reaction product of no more than three different monomers. For example, the polymer may be the reaction product of one first monomer and one ortwo second monomers, orthe reaction product of two different first monomers and one second monomer as disclosed herein. In some preferred embodiments, the polymer is the reaction product of only two different monomers, for example the reaction product of two first monomers orthe reaction product of one first monomer and one second monomer as disclosed herein (and no further monomers).

[0365] The polymers may be prepared from the first and optionally second monomers by any suitable method, as would be known to the person skilled in the art. The polymerisation reaction will typically be conducted in the presence of a suitable polymerisation catalyst, such as tin(ll) ethylhexanoate, tin(l I) oxalate, p-toluenesulfonic acid, methanesulfonic acid, or sulfuric acid.

[0366] The polymerisation reaction may be carried out for any suitable length of time, such as at least 1 hour, preferably at least 3 hours, for example at least 5 hours.

[0367] The polymerisation reaction may be carried out at any suitable temperature, such as from 50 to 300°C, preferably from 100 to 200°C

[0368] Suitable molar ratios of the first and, when present, second monomers may be used to prepare the polymers.

[0369] Thus repeat units in the polymer derived from the first and, when present, second monomers when present may be present in the polymer in any suitable molar ratio and in any suitable arrangement.

[0370] Suitably, the polymer is not further reacted after the reaction of the monomers.

[0371] Suitably the polymer may be the reaction product of monomers comprising one or more first monomers and no second monomers as defined herein.

[0372] Suitably the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers as defined herein.

[0373] Suitably when the polymer is the reaction product of monomers comprising one or more first monomers and one or more second monomers as defined herein, the polymer is a random copolymer. Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer (when present) is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0374] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0375] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more hydroxycarboxylic acid, and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0376] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer (when present) is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol.

[0377] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol.

[0378] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more hydroxycarboxylic acid, and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a monoalcohol.

[0379] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more cyclic esters of a hydroxycarboxylic acid, and wherein the or each second monomer is selected from one or more cyclic anhydride. Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers, wherein the or each first monomer is selected from one or more (for example one or two) of a hydroxycarboxylic acid or a cyclic ester thereof.

[0380] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer (when present) is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol, wherein the hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein.

[0381] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol, wherein the hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein.

[0382] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof (preferably a hydroxycarboxylic acid), and wherein the or each second monomer (when present) is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol, wherein the hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein.

[0383] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof (preferably a hydroxycarboxylic acid), and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol, wherein the hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein.

[0384] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof (preferably a hydroxycarboxylic acid), and wherein the or each second monomer (when present) is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a monoalcohol, wherein the hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein.

[0385] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof (preferably a hydroxycarboxylic acid), and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a monalcohol, wherein the hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein.

[0386] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer (when present) is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol, wherein the or each hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein, and wherein the or each cyclic ester is of the formula (I) or (II) wherein R1, R2, n2, R3, R4, n3 and n4 are as defined herein.

[0387] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol, wherein the or each hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein, and wherein the or each cyclic ester is of the formula (I) or (II) wherein R1, R2, n2, R3, R4, n3 and n4 are as defined herein.

[0388] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more hydroxycarboxylic acid, and wherein the or each second monomer (when present) is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a polyol, wherein the or each hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein.

[0389] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more hydroxycarboxylic acid, and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a polyol, wherein the or each hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein.

[0390] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more cyclic esters of a hydroxycarboxylic acid, and wherein the or each second monomer (when present) is selected from one or more cyclic anhydride, wherein the or each cyclic ester is of the formula (I) or (II) wherein R1, R2, n2, R3, R4, n3 and n4 are as defined herein.

[0391] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more cyclic esters of a hydroxycarboxylic acid, and wherein the or each second monomer is selected from one or more cyclic anhydride, wherein the or each cyclic ester is of the formula (I) or (II) wherein R1, R2, n2, R3, R4, n3 and n4 are as defined herein.

[0392] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer (when present) is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0393] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0394] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid, and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0395] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer (when present) is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol. Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol.

[0396] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more hydroxycarboxylic acid, and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a monoalcohol.

[0397] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more cyclic esters of a hydroxycarboxylic acid, and wherein the or each second monomer is selected from one or more cyclic anhydride.

[0398] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof.

[0399] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer (when present) is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol, wherein the hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein.

[0400] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol, wherein the hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein.

[0401] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer (when present) is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol, wherein the or each hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein, and wherein the or each cyclic ester is of the formula (I) or (II) wherein R1, R2, n2, R3, R4, n3 and n4 are as defined herein.

[0402] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of a hydroxycarboxylic acid or a cyclic ester thereof, and wherein the or each second monomer is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol, wherein the or each hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein, and wherein the or each cyclic ester is of the formula (I) or (II) wherein R1, R2, n2, R3, R4, n3 and n4 are as defined herein.

[0403] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more hydroxycarboxylic acid, and wherein the or each second monomer (when present) is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a polyol, wherein the or each hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein.

[0404] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more hydroxycarboxylic acid, and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a polyol, wherein the or each hydroxycarboxylic acid is of the formula R(CR2)nCOOH wherein n and R are as defined herein.

[0405] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more cyclic esters of a hydroxycarboxylic acid, and wherein the or each second monomer (when present) is selected from one or more cyclic anhydride, wherein the or each cyclic ester is of the formula (I) or (II) wherein R1, R2, n2, R3, R4, n3 and n4 are as defined herein.

[0406] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more cyclic esters of a hydroxycarboxylic acid, and wherein the or each second monomer is selected from one or more cyclic anhydride, wherein the or each cyclic ester is of the formula (I) or (II) wherein R1, R2, n2, R3, R4, n3 and n4 are as defined herein.

[0407] Suitably the or each second monomer may be selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0408] Suitably the or each second monomer may be selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol.

[0409] Suitably the or each second monomer may be selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a monoalcohol.

[0410] Suitably, when the or each second monomer is a polyol, the second monomer may be selected from ethylene glycol, trimethylol propane, 1 ,6-hexanediol and a polyalkylene glycol (such as polyethylene or polypropylene glycol, for example polypropylene glycol such as PPG 2000).

[0411] More suitably, when the or each second monomer is a polyol, the second monomer may be selected from 1 ,6-hexanediol and a polyalkylene glycol (such as polyethylene or polypropylene glycol, for example polypropylene glycol such as PPG 2000).

[0412] Suitably, when the or each second monomer is a cyclic anhydride, the second monomer may be (2-dodecen-1-yl)succinic anhydride.

[0413] Suitably, when the or each second monomer is a polycarboxylic acid or a reactive equivalent thereof, the second monomer may be diglycolic acid.

[0414] Suitably, when the or each second monomer is a monoalcohol, the second monomer may be glycerol carbonate.

[0415] Suitably, the or each second monomer (when present) may be selected from 1 ,6-hexanediol, a polyalkylene glycol (such as PPG 2000), (2-dodecen-1-yl)succinic anhydride and diglycolic acid.

[0416] When the second monomer is selected from one or more polycarboxylic acid(s) or reactive equivalent(s) thereof and one or more polyol(s), the molar ratio of the sum of the polycarboxylic acid(s) or reactive equivalent(s) thereof and the sum of the polyol(s) may be about 1 :1. Suitably, the or each first monomer may be selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid, 12-hydroxystearic acid and e-caprolactone.

[0417] Preferably, the or each first monomer may be selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and e-caprolactone.

[0418] Preferably, the or each first monomer may be selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and 12-hydroxystearic acid.

[0419] More preferably, the or each first monomer may be selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid and malic acid.

[0420] Even more preferably, the or each first monomer may be selected from one or more of ricinoleic acid, glycolic acid and citric acid.

[0421] Even more preferably, the or each first monomer may be selected from one or more of ricinoleic acid, malic acid and citric acid.

[0422] Suitably, at least one of the first monomers is 12-hydroxystearic acid.

[0423] Suitably, at least one of the first monomers is ricinoleic acid, DL-lactide ore-caprolactone.

[0424] Suitably, at least one of the first monomers is ricinoleic acid.

[0425] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and e-caprolactone (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer (when present) is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0426] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and £-caprolactone (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol. Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and e-caprolactone (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer (when present) is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol (especially a polycarboxylic acid or a reactive equivalent thereof and a monoalcohol).

[0427] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and £-caprolactone (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol (especially a polycarboxylic acid or a reactive equivalent thereof and a monoalcohol).

[0428] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and £-caprolactone (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer (when present) is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0429] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and £-caprolactone (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer is selected from one or more of a cyclic anhydride, a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0430] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and £-caprolactone (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer (when present) is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol (especially a polycarboxylic acid or a reactive equivalent thereof and a monoalcohol). Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and e-caprolactone (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol (especially a polycarboxylic acid or a reactive equivalent thereof and a monoaalcohol).

[0431] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, glycolic acid, citric acid and malic acid (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer (when present) is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0432] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, glycolic acid, citric acid and malic acid (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0433] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, glycolic acid, citric acid and malic acid (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer (when present) is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0434] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, glycolic acid, citric acid and malic acid (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0435] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, glycolic acid, citric acid and malic acid (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer (when present) is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol (especially a polycarboxylic acid or a reactive equivalent thereof and a monoalcohol).

[0436] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, glycolic acid, citric acid and malic acid (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol (especially a polycarboxylic acid or a reactive equivalent thereof and a monoalcohol).

[0437] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, glycolic acid, citric acid and malic acid (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer (when present) is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol (especially a polycarboxylic acid or a reactive equivalent thereof and a monoalcohol).

[0438] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of ricinoleic acid, glycolic acid, citric acid and malic acid (especially ricinoleic acid, citric acid and malic acid), and wherein the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof, a monoalcohol and a polyol (especially a polycarboxylic acid or a reactive equivalent thereof and a monoalcohol).

[0439] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of DL-lactide and e-caprolactone, and wherein the or each second monomer (when present) is selected from one or more cyclic anhydride.

[0440] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of DL-lactide and e-caprolactone, and wherein the or each second monomer is selected from one or more cyclic anhydride.

[0441] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is selected from one or more of DL-lactide and e-caprolactone, and wherein the or each second monomer (when present) is selected from one or more cyclic anhydride.

[0442] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the or each first monomer is selected from one or more of DL-lactide and e-caprolactone, and wherein the or each second monomer is selected from one or more cyclic anhydride.

[0443] In some embodiments, the polymer may be the reaction product of monomers comprising ricinoleic acid and one or more additional first monomers, for example one or more additional first monomers selected from glycolic acid, citric acid and malic acid (especially malic acid and citric acid), suitably in a molar ratio of from 1 :1 to 1 :2, and optionally one or more second monomers.

[0444] In some embodiments, the polymer may be the reaction product of monomers comprising ricinoleic acid and one or more additional first monomers, for example one or more additional first monomers selected from glycolic acid, citric acid and malic acid (especially malic acid and citric acid), suitably in a molar ratio of from 1 :1 to 1 :2, and one or more second monomers.

[0445] In some embodiments, the polymer may be the reaction product of monomers comprising two or more first monomers, for example selected from two or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and e-caprolactone (especially ricinoleic acid, malic acid and citric acid), and optionally one or more second monomers.

[0446] In some embodiments, the polymer may be the reaction product of monomers comprising two or more first monomers, for example selected from two or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and e-caprolactone (especially ricinoleic acid, malic acid and citric acid), and one or more second monomers.

[0447] In some embodiments, the polymer may be the reaction product of monomers comprising DL-lactide and e-caprolactone as the first monomers, and optionally one or more second monomers.

[0448] In some embodiments, the polymer may be the reaction product of monomers comprising DL-lactide and £-caprolactone as the first monomers, and one or more second monomers.

[0449] In some embodiments, the polymer may be the reaction product of monomers consisting essentially of or consisting of ricinoleic acid and one or more additional first monomers, for example one or more additional first monomers selected from glycolic acid, citric acid and malic acid (especially malic acid and citric acid), suitably in a molar ratio of from 1 :1 to 1 :2, and optionally one or more second monomers.

[0450] In some embodiments, the polymer may be the reaction product of monomers consisting essentially of or consisting of ricinoleic acid and one or more additional first monomers, for example one or more additional first monomers selected from glycolic acid, citric acid and malic acid (especially malic acid and citric acid), suitably in a molar ratio of from 1 :1 to 1 :2, and one or more second monomers.

[0451] In some embodiments, the polymer may be the reaction product of monomers consisting essentially of or consisting of two or more first monomers, for example selected from two or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and e-caprolactone (especially ricinoleic acid, glycolic acid and citric acid), and optionally one or more second monomers.

[0452] In some embodiments, the polymer may be the reaction product of monomers consisting essentially of or consisting of two or more first monomers, for example selected from two or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and e-caprolactone (especially ricinoleic acid, glycolic acid and citric acid), and one or more second monomers.

[0453] In some embodiments, the polymer may be the reaction product of monomers consisting essentially of or consisting of DL-lactide and e-caprolactone as the first monomers, and optionally one or more second monomers.

[0454] In some embodiments, the polymer may be the reaction product of monomers consisting essentially of or consisting of DL-lactide and e-caprolactone as the first monomers, and one or more second monomers.

[0455] Suitably, when a second monomer is present, the molar ratio of total of the first monomers to the total of the second monomers may be from 8:1 to 1 :1 , such as from 8:2 to 7:3.

[0456] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the one or more first monomers are selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and e-caprolactone (especially ricinoleic acid, glycolic acid and citric acid); wherein the one or more second monomers (when present) are selected from one or more of 1 ,6-hexanediol, PPG 2000, diglycolic acid and (2-dodecen-1-yl) succinic anhydride.

[0457] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the one or more first monomers are selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and e-caprolactone (especially ricinoleic acid, glycolic acid and citric acid); wherein the one or more second monomers are selected from one or more of 1 ,6-hexanediol, PPG 2000, diglycolic acid and (2-dodecen-1-yl) succinic anhydride.

[0458] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the one or more first monomers are selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and £-caprolactone (especially ricinoleic acid, citric acid and malic acid); wherein the one or more second monomers (when present) are selected from one or more of 1 ,6-hexanediol, PPG 2000, diglycolic acid and glycerol carbonate (especially 1 ,6-hexanediol and diglycolic acid).

[0459] Suitably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the one or more first monomers are selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and £-caprolactone (especially ricinoleic acid, citric acid and malic acid); wherein the one or more second monomers are selected from one or more of 1 ,6-hexanediol, PPG 2000, diglycolic acid and glycerol carbonate (especially 1 ,6-hexanediol and diglycolic acid).

[0460] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers, wherein the one or more first monomers are selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and £-caprolactone (especially ricinoleic acid, glycolic acid and citric acid); wherein the one or more second monomers (when present) are selected from one or more of 1 ,6-hexanediol, PPG 2000, diglycolic acid and (2-dodecen-1-yl) succinic anhydride.

[0461] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the one or more first monomers are selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and £-caprolactone (especially ricinoleic acid, glycolic acid and citric acid); wherein the one or more second monomers are selected from one or more of 1 ,6-hexanediol, PPG 2000, diglycolic acid and (2-dodecen-1-yl) succinic anhydride.

[0462] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers, wherein the one or more first monomers are selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and £-caprolactone (especially ricinoleic acid, citric acid and malic acid); wherein the one or more second monomers (when present) are selected from one or more of 1 ,6-hexanediol, PPG 2000, diglycolic acid and glycerol carbonate (especially 1 ,6-hexanediol and diglycolic acid).

[0463] Suitably, the polymer may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and one or more second monomers, wherein the one or more first monomers are selected from one or more of ricinoleic acid, DL-lactide, glycolic acid, citric acid, malic acid and e-caprolactone (especially ricinoleic acid, citric acid and malic acid); wherein the one or more second monomers are selected from one or more of 1 ,6-hexanediol, PPG 2000, diglycolic acid and glycerol carbonate (especially 1 ,6-hexanediol and diglycolic acid).

[0464] Preferably, the polymer is the reaction product of monomers comprising:

[0465] (i) ricinoleic acid and glycolic acid, preferably in a molar ratio of 1 :1 ;

[0466] (ii) ricinoleic acid and glycolic acid, preferably in a molar ratio of 1 :2;

[0467] (iii) ricinoleic acid and citric acid, preferably in a molar ratio of 1 :1 ;

[0468] (iv) ricinoleic acid and malic acid, preferably in a molar ratio of 1 :1 ;

[0469] (v) ricinoleic acid, 1 ,6-hexanediol, diglycolic acid and PPG 2000, preferably in a molar ratio of 0.8:0.05:0.1 :0.05;

[0470] (vi) ricinoleic acid, 1 ,6-hexanediol, diglycolic acid and PPG 2000, preferably in a molar ratio of 0.7:0.075:0.15:0.075;

[0471] (vii) DL-lactide, e-caprolactone and (2-dodecen-1-yl)succinic anhydride, preferably in a molar ratio of 1 :1 :0.01 ; or

[0472] (viii) ricinoleic acid and glycerol carbonate, preferably in a molar ratio of 1 :1.

[0473] Preferably, the polymer is the reaction product of monomers comprising:

[0474] (i) ricinoleic acid and glycolic acid, preferably in a molar ratio of 1 :1 ;

[0475] (ii) ricinoleic acid and glycolic acid, preferably in a molar ratio of 1 :2;

[0476] (iii) ricinoleic acid and citric acid, preferably in a molar ratio of 1 :1 ;

[0477] (iv) ricinoleic acid and malic acid, preferably in a molar ratio of 1 :1 ;

[0478] (v) ricinoleic acid, 1 ,6-hexanediol, diglycolic acid and PPG 2000, preferably in a molar ratio of 0.8:0.05:0.1 :0.05;

[0479] (vi) ricinoleic acid, 1 ,6-hexanediol, diglycolic acid and PPG 2000, preferably in a molar ratio of 0.7:0.075:0.15:0.075; or

[0480] (vii) DL-lactide, e-caprolactone and (2-dodecen-1-yl)succinic anhydride, preferably in a molar ratio of 1 :1 :0.01.

[0481] Preferably, the polymer is the reaction product of monomers consisting essentially of or consisting of:

[0482] (i) ricinoleic acid and glycolic acid, preferably in a molar ratio of 1 :1 ;

[0483] (ii) ricinoleic acid and glycolic acid, preferably in a molar ratio of 1 :2; (iii) ricinoleic acid and citric acid, preferably in a molar ratio of 1 :1 ;

[0484] (iv) ricinoleic acid and malic acid, preferably in a molar ratio of 1 :1 ;

[0485] (v) ricinoleic acid, 1 ,6-hexanediol, diglycolic acid and PPG 2000, preferably in a molar ratio of 0.8:0.05:0.1:0.05;

[0486] (vi) ricinoleic acid, 1 ,6-hexanediol, diglycolic acid and PPG 2000, preferably in a molar ratio of 0.7:0.075:0.15:0.075;

[0487] (vii) DL-lactide, e-caprolactone and (2-dodecen-1-yl)succinic anhydride, preferably in a molar ratio of 1 :1 :0.01 ; or

[0488] (viii) ricinoleic acid and glycerol carbonate, preferably in a molar ratio of 1 :1.

[0489] Preferably, the polymer is the reaction product of monomers consisting essentially of or consisting of:

[0490] (i) ricinoleic acid and glycolic acid, preferably in a molar ratio of 1 :1 ;

[0491] (ii) ricinoleic acid and glycolic acid, preferably in a molar ratio of 1 :2;

[0492] (iii) ricinoleic acid and citric acid, preferably in a molar ratio of 1 :1 ;

[0493] (iv) ricinoleic acid and malic acid, preferably in a molar ratio of 1 :1 ;

[0494] (v) ricinoleic acid, 1 ,6-hexanediol, diglycolic acid and PPG 2000, preferably in a molar ratio of 0.8:0.05:0.1:0.05;

[0495] (vi) ricinoleic acid, 1 ,6-hexanediol, diglycolic acid and PPG 2000, preferably in a molar ratio of 0.7:0.075:0.15:0.075; or

[0496] (vii) DL-lactide, e-caprolactone and (2-dodecen-1-yl)succinic anhydride, preferably in a molar ratio of 1 :1 :0.01.

[0497] More preferably, the polymer is the reaction product of monomers comprising:

[0498] (i) ricinoleic acid and glycolic acid, preferably in a molar ratio of 1 :1 ;

[0499] (ii) ricinoleic acid and glycolic acid, preferably in a molar ratio of 1 :2;

[0500] (iii) ricinoleic acid and citric acid, preferably in a molar ratio of 1 :1 ;

[0501] (iv) ricinoleic acid and malic acid, preferably in a molar ratio of 1 :1 ;

[0502] (v) ricinoleic acid, 1 ,6-hexanediol, diglycolic acid and PPG 2000, preferably in a molar ratio of 0.8:0.05:0.1:0.05; or

[0503] (vi) ricinoleic acid, 1 ,6-hexanediol, diglycolic acid and PPG 2000, preferably in a molar ratio of 0.7:0.075:0.15:0.075.

[0504] More preferably, the polymer is the reaction product of monomers consisting essentially of or consisting of:

[0505] (i) ricinoleic acid and glycolic acid, preferably in a molar ratio of 1 :1 ;

[0506] (ii) ricinoleic acid and glycolic acid, preferably in a molar ratio of 1 :2;

[0507] (iii) ricinoleic acid and citric acid, preferably in a molar ratio of 1 :1 ;

[0508] (iv) ricinoleic acid and malic acid, preferably in a molar ratio of 1 :1 ; (v) ricinoleic acid, 1 ,6-hexanediol, diglycolic acid and PPG 2000, preferably in a molar ratio of 0.8:0.05:0.1 :0.05; or

[0509] (vi) ricinoleic acid, 1 ,6-hexanediol, diglycolic acid and PPG 2000, preferably in a molar ratio of 0.7:0.075:0.15:0.075.

[0510] Preferably, the polymer is the reaction product of monomers comprising:

[0511] (i) ricinoleic acid and citric acid, preferably in a molar ratio of 1 :1 ;

[0512] (ii) ricinoleic acid and malic acid, preferably in a molar ratio of 1 :1 ; or

[0513] (iii) ricinoleic acid and glycerol carbonate, preferably in a molar ratio of 1 :1.

[0514] Preferably, the polymer is the reaction product of monomers consisting essentially of or consisting of:

[0515] (i) ricinoleic acid and citric acid, preferably in a molar ratio of 1 :1 ;

[0516] (ii) ricinoleic acid and malic acid, preferably in a molar ratio of 1 :1 ; or

[0517] (iii) ricinoleic acid and glycerol carbonate, preferably in a molar ratio of 1 :1.

[0518] Preferably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the or each first monomer is a hydroxycarboxylic acid or a cyclic ester thereof selected from one or more of glycolic acid, lactic acid, hydroxy butyric acid, hydroxyvaleric acid, hydroxycaproic acid, hydroxystearic acid (preferably 12-hydroxystearic acid), dihydroxystearic acid, 2,2-bis(hydroxymethyl)propionic acid, mandelic acid, ricinoleic acid, malic acid, tartaric acid, citric acid, y-butyrolactone, 6-valerolactone, e-caprolactone, menthide, D-lactide, L-lactide, and DL-lactide.

[0519] Preferably, the polymer may be the reaction product of monomers comprising one or more first monomers, wherein the polymer is a homopolymer and the first monomer is a hydroxycarboxylic acid orthe cyclic ester thereof selected from one of glycolic acid, lactic acid, hydroxy butyric acid, hydroxyvaleric acid, hydroxycaproic acid, hydroxystearic acid (preferably 12-hydroxystearic acid), dihydroxystearic acid, 2,2-bis(hydroxymethyl)propionicacid, mandelic acid, ricinoleic acid, malic acid, tartaric acid, citric acid, y-butyrolactone, b-valerolactone, e-caprolactone, menthide, D-lactide, L-lactide, and DL-lactide.

[0520] Preferably, the polymer may be the reaction product of monomers comprising one or more first monomers, wherein the polymer is a homopolymer and the first monomer is a hydroxycarboxylic acid orthe cyclic ester thereof selected from one of hydroxystearic acid and ricinoleic acid.

[0521] Preferably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the polymer is a copolymer and the or each first monomer is a hydroxycarboxylic acid or the cyclic ester thereof selected from two or more of DL-lactide, citric acid ore-caprolactone; or the each first monomer is a hydroxycarboxylic acid or the cyclic ester thereof selected from two or more of ricinoleicacid, glycolic acid, mandelic acid, malic acid, and citric acid (especially ricinoleic acid, citric acid and malic acid).

[0522] Preferably, the polymer may be the reaction product of monomers comprising one or more first monomers and one or more second monomers, wherein the polymer is a copolymer and the or each first monomer is a hydroxycarboxylic acid or the cyclic ester thereof selected from one or more of ricinoleic acid, glycolic acid, citric acid and malic acid (especially ricinoleic acid, citric acid and malic acid), and the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a polyol.

[0523] The polymer formed from the first and optional second monomers may comprise a suitable number of total monomer units (i.e. repeat units). For example, the polymer may comprise at least 4 monomer units. In other words, the polymer may comprise a total of at least 4 monomer units including the first and optional second monomers. Suitably, the polymer may comprise from 4 to 50 monomer units, preferably from 4 to 30 monomer units.

[0524] Suitably, the polymer has a number average molecular weight of from 1 ,000 to 50,000 Daltons, preferably from 1 ,000 to 15,000 Daltons (for example from 2,000 to 7,000 Daltons).

[0525] Preferably, the polymer is substantially free of silicon atoms. By substantially free of silicon atoms we mean that the polymer contains less than 1 wt% of silicon in the polymer, preferably less than 0.5 wt% of silicon in the polymer. More preferably, the polymer is free of silicon atoms, by which we mean that it is not possible to detect silicon in the polymer. Suitable methods of measuring the amount of silicon in a polymer are well known to those skilled in art and include elemental analysis and inductively coupled plasma (ICP) spectroscopy.

[0526] Preferably, the polymer is substantially free of fluorine atoms. The polymer may be substantially free of halogen atoms. By substantially free of fluorine or halogen atoms we mean that the polymer contains less than 1 wt% of fluorine or halogen in the polymer, preferably less than 0.5 wt% of fluorine or halogen in the polymer. More preferably, the polymer is free of fluorine atoms. The polymer may be free of halogen atoms. By free of fluorine or halogen atoms we mean that it is not possible to detect fluorine or halogen in the polymer. Suitable methods of measuring the amount of fluorine or halogen in a polymer are well known to those skilled in art and include elemental analysis and inductively coupled plasma (ICP) spectroscopy.

[0527] Preferably, the polymer is substantially free of quaternary ammonium moieties. By substantially free of quaternary ammonium moieties we mean that the polymer contains less than 1 wt% of quaternary nitrogen atoms in the polymer, preferably less than 0.5 wt% of quaternary nitrogen atoms in the polymer. More preferably, the polymer is free of quaternary ammonium moieties, by which we mean that it is not possible to detect quaternary ammonium moieties in the polymer.

[0528] According to a second aspect of the invention, there is provided a concentrate composition comprising one or more polymers and optionally at least one solvent, wherein the concentrate composition comprises at least 20 wt% of the one or more polymers, and wherein the or each polymer is the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is a hydroxycarboxylic acid or a cyclic ester thereof and the or each second monomer is one or more of the following:

[0529] (i) cyclic anhydride;

[0530] (ii) polycarboxylic acid or reactive equivalent thereof;

[0531] (iii) monocarboxylic acid or ester thereof;

[0532] (iv) polyol;

[0533] (v) epoxide compound;

[0534] (vi) polyfunctional monomer having a reactive amino group;

[0535] (vii) monoalcohol; and

[0536] (viii) monofunctional monomer having a reactive amino group.

[0537] The concentrate composition may comprise at least 30 wt%, at least 40 wt%, at least 50 wt%, at least 60 wt%, at least 70 wt%, or at least 80 wt% of the one or more polymers based on the total weight of the concentrate composition. The concentrate composition additionally may comprise 99 wt% or less, such as 95 wt% or less, for example 90 wt% or less of the one or more polymers based on the total weight of the concentrate composition. The concentrate composition may comprise from 20 to 99 wt%, preferably from 20 to 95 wt%, for example from 50 to 90 wt%, of the one or more polymers based on the total weight of the concentrate composition.

[0538] References herein to the amount of polymer in the concentrate composition are intended to refer to the total of the or each polymer as defined herein that is included in the composition, i.e. based on the total weight of the concentrate composition.

[0539] Suitably, the concentrate composition may be stable for at least 1 week, preferably at least 4 weeks, most preferably at least 8 weeks under ambient conditions (for example, at atmospheric pressure and at a temperature of 20°C). The stability of the concentrate composition may be determined visually. Suitably, the concentrate composition is unstable when it shows creaming, sedimentation, separation, or a combination thereof. Suitably, the concentrate composition may comprise at least 20 wt%, such as at least 30 wt%, at least 40 wt%, at least 50 wt%, at least 60 wt%, at least 70 wt%, or at least 80 wt% of the one or more polymers and the concentrate composition may be stable for at least 1 week, preferably at least 4 weeks or at least 8 weeks, most preferably at least 3, 6, 12 or 24 months, under ambient conditions.

[0540] Suitably, the concentrate composition may be flowable. The meaning of a “flowable” composition is well known to those skilled in the art. Typically, flowable compositions are pourable from a container at 20°C. Flowable compositions may be poured without needing to heat the composition above 20°C or manually scraping the composition. Suitably, the concentrate composition may have a viscosity of 7,000 cP or less, preferably 3,500 cP or less, at 20°C. Suitably, the concentrate composition may comprise at least 20 wt%, such as at least 30 wt%, at least 40 wt%, at least 50 wt%, at least 60 wt%, at least 70 wt%, or at least 80 wt% of the polymer and the concentrate composition may be flowable.

[0541] Suitably the concentrate composition of the second aspect is substantially free of silicon atoms. By substantially free of silicon atoms we mean that the composition contains less than 1 wt%, preferably less than 0.5 wt%, of silicon in the composition. More preferably, the composition is free of silicon atoms, by which we mean that it is not possible to detect silicon in the composition. Suitable methods of measuring the amount of silicon in a composition are well known to those skilled in art and include elemental analysis and inductively coupled plasma (ICP) spectroscopy.

[0542] The polymer referred to in relation to the second aspect may comprise the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers as defined herein. The polymer referred to in relation to the second aspect may be the reaction product of monomers consisting essentially of or consisting of one or more first monomers and optionally one or more second monomers as defined herein.

[0543] Features of the polymer, and of the first monomers (and the second monomers when present), in relation to the second aspect of the invention are as set out herein in relation to the first aspect of the invention.

[0544] The concentrate composition of the second aspect may optionally comprise any suitable solvent, such as for example a polar solvent, such as a polar protic solvent. Preferably, the concentrate composition comprises at least one solvent.

[0545] The solvent may be an aqueous solvent. Thus, the concentrate composition may be an aqueous composition. The term “aqueous solvent” herein is considered to mean water or mixtures of water and at least one water miscible solvent. Water miscible solvents may include alcohols and substantially water-miscible organic solvents. Preferably the aqueous solvent is water. When the solvent is an aqueous solvent, the concentrate composition may be in the form of an emulsion.

[0546] The solvent may be a non-aqueous solvent. The non-aqueous solvent suitably comprises an organic solvent, such as an alcohol. The non-aqueous solvent preferably does not comprise any surfactant.

[0547] When the solvent is a non-aqueous solvent, it is preferably miscible with water. Preferably, the non-aqueous solvent is not an oil.

[0548] Suitable such alcohols for use in the solvent include monohydric alcohols, polyhydric alcohols, alkoxy alcohols and aryloxy alcohol.

[0549] Suitable alcohols are monohydric alcohols, polyhydric alcohols and alkoxy alcohols.

[0550] Preferred alcohols are miscible with water.

[0551] Suitable simple monohydric alcohols include methanol, ethanol, isopropanol and butanol.

[0552] The solvent may comprise a polyhydric alcohol or an alkoxyalcohol.

[0553] Suitable alkoxy alcohols include diethylene glycol monobutyl ether, 3-methoxy-3-methyl-1-butanol and 2-butoxyethanol.

[0554] Suitable aryloxy alcohols include 2-phenoxyethanol.

[0555] Suitable polyhydric alcohols include glycerol, ethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol and 2-methylpentanediol.

[0556] Suitable polyhydric alcohols include glycerol, ethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol and polypropylene glycol.

[0557] Preferably, the non-aqueous solvent comprises a monohydric alcohol such as isopropanol.

[0558] The concentrate composition may comprise at least 20 wt%, at least 30 wt%, at least 40 wt%, at least 50 wt%, at least 60 wt% or at least 70 wt% of the at least one solvent (when present) based on the total weight of the concentrate composition. The concentrate composition additionally may comprise 80 wt% or less, such as 70 wt% or less, of the at least one solvent (when present) based on the total weight of the concentrate composition. The concentrate composition may comprise from 20 to 80 wt%, preferably from 20 to 75 wt%, such as from 50 to 80 wt% or from 50 to 75 wt%, of the at least one solvent (when present) based on the total weight of the concentrate composition.

[0559] The concentrate composition of the second aspect may additionally comprise one or more surfactants (in particular when the solvent is an aqueous solvent). Preferably, the concentrate composition of the second aspect comprises one or more surfactants (in particular when the solvent is an aqueous solvent). Any suitable surfactant(s) may be included, such as for example one or more surfactants selected from anionic surfactants, cationic surfactants, non-ionic surfactants, and amphoteric or zwitterionic surfactants. One or more non-ionic surfactant(s) are preferred.

[0560] The concentrate composition may comprise an anionic surfactant. Suitable anionic surfactants may include sulfate surfactants (such as mono- or di-alkyl sulfates or alkyl ether sulfates), sulfonate surfactants, alkyl ether carboxylate surfactants, sarcosinate surfactants, phosphate surfactants, succinate surfactants, sulfosuccinate surfactants, sulfoacetate surfactants, isethionate surfactants, taurate surfactants, amino acid surfactants such as glutamates and glycinates, lactylate surfactants, and fatty acid salts. Particularly exemplary salts of the above, where applicable, are the sodium, potassium, ammonium, magnesium and triethanolamine salts.

[0561] The concentrate composition may comprise a cationic surfactant. The cationic surfactant may be an ammonium salt such as an alkyl trimethyl ammonium salt, a dialkyl dimethyl ammonium salt, an alkyl-(N-hydroxyethyl)-dimethyl ammonium salt, or an alkyldimethylbenzylammonium salt (i.e. a benzalkonium salt). The salt may be a halide, hydroxide, sulfate, hydrogensulfate, phosphate, or carboxylate salt. The salt is suitably a halide salt, such as a fluoride, chloride, or bromide salt. The salt may be a carboxylate salt, such as formate or acetate salt. Preferably, the salt is chloride.

[0562] The concentrate composition may comprise a non-ionic surfactant.

[0563] Suitable non-ionic surfactants for use herein include castor oil, alcohol alkoxylates (such as alcohol ethoxylates, alcohol propoxylates, and ethylene oxide / propylene oxide copolymer derived surfactants), aliphatic esters, aromatic esters, sugar esters (such as sorbitan esters), alkyl (poly)glycosides, fatty acid alkoxylates (such as fatty acid ethoxylates and fatty acid propoxylates), or polyethylene glycol esters (including partial esters), glycerol esters (including glycerol partial esters and glycerol triesters), fatty alcohols (such as cetearyl alcohol, lauryl alcohol, stearyl alcohol, behenyl alcohol), alkanolamides, fatty amine alkoxylates (such as fatty amine ethoxylates and fatty amine propoxylates) and polyglyceryl fatty acid esters. Suitable non-ionic surfactants for use herein include castor oil, alcohol alkoxylates (such as alcohol ethoxylates, alcohol propoxylates, and ethylene oxide / propylene oxide copolymer derived surfactants), aliphatic esters, aromatic esters, sugar esters (such as sorbitan esters), alkyl (poly)glycosides, fatty acid alkoxylates (such as fatty acid ethoxylates and fatty acid propoxylates), or polyethylene glycol esters (including partial esters), glycerol esters (including glycerol partial esters and glycerol triesters), fatty alcohols (such as cetearyl alcohol, lauryl alcohol, stearyl alcohol, behenyl alcohol), and alkanolamides.

[0564] Preferably, the non-ionic surfactant may be selected from one or more of a sugar ester (such as a sorbitan ester) and a fatty amine alkoxylate (such as a fatty amine ethoxylate or fatty amine propoxylate).

[0565] Suitable sugar esters may include alkoxylated (such as ethoxylated) sugar esters. For example, the sugar ester may comprise an alkoxylated (such as ethoxylated) sugar ester of a fatty acid, such as oleic acid. An example of a preferred sugar ester surfactant is Tween® 80.

[0566] Suitable fatty amine alkoxylates may include fatty amine ethoxylates and fatty amine propoxylates. Fatty amine ethoxylates are preferred. The fatty amine alkoxylates may be based on any suitable fatty alcohol. An example of a preferred fatty amine alkoxylate is a fatty amine ethoxylate such as Empilan® AMT 11 , which is a fatty amine ethoxylate containing 11 moles of ethylene oxide.

[0567] The concentrate composition may comprise an amphoteric or zwitterionic surfactant. The amphoteric or zwitterionic surfactant may be selected from betaines (such as alkyl betaines and alkylamidopropyl betaines), amphoacetates, diamphoacetates, and amine oxides (such as alkylamine oxides and alkylamidopropyl amine oxides). Suitable amphoteric or zwitterionic surfactants include lauryl betaine, cocamidopropyl betaine, sodium lauroamphoacetate, sodium cocoamphoacetate, disodium cocoamphodiacetate, lauramine oxide, C12-18 alkyldimethylamine oxide, myristamine oxide, and cocamidopropyl amine oxide.

[0568] The one or more surfactants may be selected from a fatty alkyl amphoacetate (for example cocoyl amphoacetate, lauryl amphoacetate), an alkyl (poly)glycoside (for example lauryl glycoside), an acyl glycinate (for example cocoyl glycinate), a sulfosuccinate, an amphodiacetate and a fatty alcohol ether carboxylate (for example C8-12 alkyl ether (6-11 moles EO) carboxylate).

[0569] The concentrate composition may comprise at least 1 wt%, at least 3 wt%, at least 5 wt%, of the one or more surfactants (when present) based on the total weight of the concentrate composition. The concentrate composition additionally may comprise 15 wt% or less, such as 10 wt% or less, of the one or more surfactants (when present) based on the total weight of the concentrate composition. The concentrate composition may comprise from 1 to 15 wt%, preferably from 3 to 10 wt% of the one or more surfactants (when present) based on the total weight of the concentrate composition.

[0570] The concentrate composition of the second aspect may comprise the one or more surfactants in an amount of from 1 to 100 wt%, suitably from 5 to 50 wt%, preferably from 5 to 25 wt% or from 10 to 25 wt% based on the total weight of the one or more polymers.

[0571] When the concentrate composition comprises the one or more polymers, the at least one solvent and the one or more surfactants, the composition may comprise:

[0572] (i) from 20 to 60 wt% of the one or more polymers;

[0573] (ii) from 35 to 60 wt% of the at least one solvent; and

[0574] (iii) from 1 to 15 wt% of the one or more surfactants;

[0575] based on the total weight of the concentrate composition.

[0576] When the concentrate composition comprises the one or more polymers, the at least one solvent and the one or more surfactants, the composition may comprise:

[0577] (i) from 20 to 45 wt% of the one or more polymers;

[0578] (ii) from 50 to 75 wt% of the at least one solvent; and

[0579] (iii) from 1 to 15 wt% of the one or more surfactants;

[0580] based on the total weight of the concentrate composition.

[0581] When the concentrate composition comprises the one or more polymers, the at least one solvent and the one or more surfactants, the composition may comprise:

[0582] (i) from 20 to 40 wt% of the one or more polymers;

[0583] (ii) from 50 to 75 wt% of the at least one solvent; and

[0584] (iii) from 3 to 10 wt% of the one or more surfactants;

[0585] based on the total weight of the concentrate composition.

[0586] According to a third aspect of the invention, there is provided a use of a surfactant to emulsify at least one polymer in an aqueous concentrate composition, wherein the aqueous concentrate composition comprises at least 20 wt% of the one or more polymers, wherein the polymer is the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is a hydroxycarboxylic acid or a cyclic ester thereof and the or each second monomer is one or more of the following:

[0587] (i) cyclic anhydride;

[0588] (ii) polycarboxylic acid or reactive equivalent thereof; (iii) monocarboxylic acid or ester thereof;

[0589] (iv) polyol;

[0590] (v) epoxide compound;

[0591] (vi) polyfunctional monomer having a reactive amino group;

[0592] (vii) monoalcohol; and

[0593] (viii) monofunctional monomer having a reactive amino group.

[0594] The polymer referred to in relation to the third aspect may comprise the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers as defined herein. The polymer referred to in relation to the third aspect may be the reaction product of monomers consisting essentially of or consisting of one (preferably consisting of) or more first monomers and optionally one or more second monomers as defined herein.

[0595] Features of the polymer, and of the first monomers (and the second monomers when present), in relation to the third aspect of the invention are as set out herein in relation to the first aspect of the invention. Features of the surfactant in relation to the third aspect of the invention are as set out herein in relation to the second aspect of the invention.

[0596] According to a fourth aspect of the invention, there is provided a method of emulsifying at least one polymer in an aqueous composition to make an aqueous polymer concentrate composition, wherein the aqueous polymer concentrate composition comprises at least 20 wt% of the one or more polymers, the method comprising admixing a surfactant with the polymer in an aqueous composition, wherein the polymer is the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is a hydroxycarboxylic acid or a cyclic ester thereof and the or each second monomer is one or more of the following:

[0597] (i) cyclic anhydride;

[0598] (ii) polycarboxylic acid or reactive equivalent thereof;

[0599] (iii) monocarboxylic acid or ester thereof;

[0600] (iv) polyol;

[0601] (v) epoxide compound;

[0602] (vi) polyfunctional monomer having a reactive amino group;

[0603] (vii) monoalcohol; and

[0604] (viii) monofunctional monomer having a reactive amino group.

[0605] The polymer referred to in relation to the fourth aspect may comprise the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers as defined herein. The polymer referred to in relation to the fourth aspect may be the reaction product of monomers consisting essentially of or consisting of (preferably consisting of) one or more first monomers and optionally one or more second monomers as defined herein.

[0606] Features of the polymer, and of the first monomers (and the second monomers when present), in relation to the fourth aspect of the invention are as set out herein in relation to the first aspect of the invention. Features of the surfactant in relation to the fourth aspect of the invention are as set out herein in relation to the second aspect of the invention.

[0607] Examples

[0608] The invention will now be further described with reference to the following non-limiting examples.

[0609] Example 1 - general method for synthesis of polymers using hydroxycarboxylic acid(s) as a monomer

[0610] The hydroxycarboxylic acid monomer(s) were combined with optional further monomer(s) (where used). Tin(ll) ethylhexanoate (0.5 wt% relative to the total weight of monomers) was added. The reaction mass was heated at 160°C for 6 hours. The resulting polymer was decanted from the reaction flask, and no further purification was carried out.

[0611] Example 2 - general method for synthesis of polymers using cyclic ester of a hydroxycarboxylic acid as a monomer

[0612] The cyclic hydroxycarboxylic ester(s) were combined with an initiator (second monomer) and tin(ll) ethylhexanoate (0.5 wt% relative to the total weight of monomers) was added. The reaction mass was heated at 140°C for 6 hours. The resulting polymer was decanted from the reaction flask, and no further purification was carried out.

[0613] Polymers 1 to 19 were prepared, using the monomers, reaction stoichiometries and synthesis procedures as set out in Table 1. Table 1

[0614]

[0615]

[0616]

[0617]

[0618]

[0619]

[0620] Table 2 - abbreviations and chemical names

[0621]

[0622] Example 3 - Preparation of concentrated aqueous emulsions.

[0623] A polymer (20 wt%), surfactant (5 wt% active unless otherwise indicated in Table 3) and deionized water (balance, i.e. 75 wt% when surfactant is 5 wt%) were combined with a vortex mixer. The resulting mixture was left to stand at ambient temperature and the emulsion quality overtime was observed.

[0624] The results are shown in Table 3. If the resulting mixture formed a stable emulsion, this is entered as “Stable”. If recorded as “Stable”, the stability time indicates the last time-point which was assessed.

[0625] Table 3

[0626]

[0627] * Tween® 80 is an ethoxylated sorbitan ester based on a natural fatty acid (oleic acid) commercially available from Croda International Pic (Goole, UK).

[0628] Unless otherwise stated herein, the reference to “liquid”, “gel” and “solid” refer to a state at 25 °C and standard pressure (101 ,325 Pa).

[0629] Attention is directed to all papers and documents which are filed concurrently with or previous to this specification in connection with this application and which are open to public inspection with this specification, and the contents of all such papers and documents are incorporated herein by reference.

[0630] All of the features disclosed in this specification (including any accompanying claims, and drawings), and / or all of the steps of any method or process so disclosed, may be combined in any combination, except combinations where at least some of such features and / or steps are mutually exclusive.

[0631] Each feature disclosed in this specification (including any accompanying claims, and drawings) may be replaced by alternative features serving the same, equivalent or similar purpose, unless expressly stated otherwise. Thus, unless expressly stated otherwise, each feature disclosed is one example only of a generic series of equivalent or similar features.

[0632] The invention is not restricted to the details of the foregoing embodiment(s). The invention extends to any novel one, or any novel combination, of the features disclosed in this specification (including any accompanying claims, and drawings), or to any novel one, or any novel combination, of the steps of any method or process so disclosed.

Claims

1. Claims1. A polymer, wherein the polymer is the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is a hydroxycarboxylic acid or a cyclic ester thereof and the or each second monomer is one or more of the following:3.(i) cyclic anhydride;4.(ii) polycarboxylic acid or reactive equivalent thereof;5.(iii) monocarboxylic acid or ester thereof;6.(iv) polyol;7.(v) epoxide compound;8.(vi) polyfunctional monomer having a reactive amino group;9.(vii) monoalcohol; and10.(viii) monofunctional monomer having a reactive amino group.

2. The polymer according to claim 1 , wherein the polymer is a polyester.

3. The polymer according to any preceding claim, wherein the polymer is a homopolymer.

4. The polymer according to any of claims 1 to 2, wherein the polymer is a copolymer.

5. The polymer according to any preceding claim, wherein the or each first monomer is a hydroxycarboxylic acid or a cyclic ester thereof selected from one or more of glycolic acid, lactic acid, hydroxy butyric acid, hydroxyvaleric acid, hydroxycaproic acid, hydroxystearic acid (preferably 12-hydroxystearic acid), dihydroxystearic acid, 2,2-bis(hydroxymethyl)propionic acid, mandelic acid, ricinoleic acid, malic acid, tartaric acid, citric acid, y-butyrolactone, 6-valerolactone, e-caprolactone, menthide, D-lactide, L-lactide, and DL-lactide.

6. The polymer according to claim 3, wherein the polymer is a homopolymer and the first monomer is a hydroxycarboxylic acid or the cyclic ester thereof selected from one of glycolic acid, lactic acid, hydroxy butyric acid, hydroxyvaleric acid, hydroxycaproic acid, hydroxystearic acid (preferably 12-hydroxystearic acid), dihydroxystearic acid, 2,2-bis(hydroxymethyl)propionic acid, mandelic acid, ricinoleic acid, malic acid, tartaric acid, citric acid, y-butyrolactone, 6-valerolactone, e-caprolactone, menthide, D-lactide, L-lactide, and DL-lactide.

7. The polymer according to claim 3, wherein the polymer is a homopolymer and the first monomer is a hydroxycarboxylic acid or the cyclic ester thereof selected from one of hydroxystearic acid and ricinoleic acid.

8. The polymer according to claim 4, wherein the polymer is a copolymer and the or each first monomer is a hydroxycarboxylic acid or the cyclic ester thereof selected from two or more of DL-lactide, citric acid or e-caprolactone; or the each first monomer is a hydroxycarboxylic acid or the cyclic ester thereof selected from two or more of ricinoleic acid, glycolic acid, mandelic acid, malic acid, and citric acid.

9. The polymer according to claim 4, wherein the polymer is a copolymer and the or each first monomer is a hydroxycarboxylic acid or the cyclic ester thereof selected from one or more of ricinoleic acid, glycolic acid, citric acid and malic acid, and the or each second monomer is selected from one or more of a polycarboxylic acid or a reactive equivalent thereof and a polyol.

10. The polymer according to any preceding claim, wherein the polymer comprises at least 4 monomer units and / or wherein the polymer has a number average molecular weight of from 1 ,000 to 50,000 Daltons, preferably from 1 ,000 to 15,000 Daltons (for example from 2,000 to 7,000 Daltons).

11. The polymer according to any preceding claim, wherein the polymer is substantially free of silicon atoms.

12. A concentrate composition comprising one or more polymers and optionally at least one solvent, wherein the concentrate composition comprises at least 20 wt% of the one or more polymers, and wherein the or each polymer is the reaction product of monomers comprising one or more first monomers and optionally one or more second monomers, wherein the or each first monomer is a hydroxycarboxylic acid or a cyclic ester thereof and the or each second monomer is one or more of the following:21.(i) cyclic anhydride;22.(ii) polycarboxylic acid or reactive equivalent thereof;23.(iii) monocarboxylic acid or ester thereof;24.(iv) polyol;25.(v) epoxide compound;26.(vi) polyfunctional monomer having a reactive amino group;27.(vii) monoalcohol; and28.(viii) monofunctional monomer having a reactive amino group.

13. The concentrate composition according to claim 12, wherein the composition comprises at least 30 wt%, at least 40 wt%, at least 50 wt%, at least 60 wt%, at least 70 wt%, or at least 80 wt% of one or more polymers.

14. The concentrate composition according to claim 12 or 13, wherein the composition additionally comprises one or more surfactants.

15. The concentrate composition according to claim 14, wherein the one or more surfactants are independently selected from anionic surfactants, cationic surfactants, non-ionic surfactants, and amphoteric or zwitterionic surfactants (preferably non-ionic surfactants).

16. The concentrate composition according to claim 15, wherein the one or more surfactants are independently selected from one or more of a sugar ester (such as a sorbitan ester) and a fatty amine alkoxylate (such as a fatty amine ethoxylate or fatty amine propoxylate).

17. The concentrate composition according to any of claims 12 to 16, wherein the concentrate composition is stable for at least 3, 6, 12 or 24 months under ambient conditions.

18. The concentrate composition according to any of claims 12 to 17, wherein the concentrate composition is flowable.

19. The concentrate composition according to claim 18, wherein the concentrate composition has a viscosity of 7,000 cP or less, preferably 3,500 cP or less at 20°C.