Curable polyester useful in coatings, INKS and adhesives

Abstract

This invention relates to polyester compounds and compositions comprising such polyester compounds. The invention also relates to their use in formulations for coatings, inks and adhesives, as well as in solvent-resistant encapsulant formulations, such as coatings for batteries.

Description

TITLE: CURABLE POLYESTER USEFUL IN COATINGS, INKS AND ADHESIVES FIELD OF THE INVENTION

[0001] This invention relates to curable polyester compounds and compositions comprising such polyester compounds. The invention also relates to their use in formulations for coatings, inks and adhesives, as well as in solvent-resistant encapsulant formulations, such as coatings for batteries.BACKGROUND

[0002] The use of polyester compounds containing curable functional groups, such as acrylates, methacrylates, or epoxy groups, is well-established in the coatings, inks, and adhesives industries. These reactive groups allow the polyester compounds to undergo polymerization or crosslinking upon exposure to UV light, heat, or chemical curing agents, forming durable, resistant films or strong bonds.

[0003] These polymer compounds are typically obtained from the esterification of diols with diacids. Among others, US 4,206,025 describes the use of dicarboxylic acid selected from the group consisting of acids in which each carboxyl group is in the alpha position with respect to groups chosen from -CH2-, > CH- and quaternary-carbon groups; acids in which one carboxyl group is in the alpha position with respect to a > CH- group, the other carboxyl group being in the alpha position with respect to a quaternary -carbon group, as well as the anhydrides of said acids. Specific examples of such acids are malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic and the like acids and their anhydrides (both carboxy groups in the alpha position with respect to a -CH2- group); maleic, fumaric, cyclohexane-l,4-dicarboxylic, 1,2-dihydrophthalic, Δ4 -tetrahydrophthalic and the like acids and their anhydrides (both carboxy groups in the alpha position with respect to a > CH-group); 1,6-dihydrophthalic and the like acids and their anhydrides (one carboxy group in the alpha position with respect to a > CH- group, the other in the alpha position with respect to a quaternary-carbon group); o-phthalic, isophthalic, terephthalic, 3,6-dihydrophthalic-l,2; 4,5-dihydrophthalic-1,2; tetrachloro(or bromo)phthalic and the like acids and their anhydrides (both carboxy groups in the alpha position with respect to a quaternary -carbon group).

[0004] Most diacid products used in polyester manufacturing are not pure and often contain monoacids and polyacids due to the complexity of their production or purification processes. These by-products can interfere with the esterification process, affecting the polymerization and crosslinking efficiency of the resulting polyesters. The industry has made significant efforts to improve the purity of diacids to enhance the performance and consistency of polyesters, offering various grades of diacids with different purity levels.

[0005] In fact, some of the polyester compounds disclosed in prior art are derived from mixtures of dicarboxylic and polycarboxylic acids.

[0006] Notably, US 3,952,032 describes the use of an organic carboxylic acid radical with a hydrophobic character, typically derived from a higher fatty acid containing 14 to 90 carbon atoms, preferably 18 to 54. The acid may be saturated or unsaturated, straight or branched, and contain 1 to 6 carboxyl groups, with functional derivatives such as acid halides, anhydrides, esters, and salts also being suitable. Several examples of dicarboxylic and polycarboxylic acids which can be used are provided, including EMPOL commercial products and in particular, EMPOL®1010 (a commercial dibasic C36dimer, containing 3% trimer and no monobasic acid), EMPOL®1022 (a dimer acid containing 19-22% trimer and 5% monobasic acid) and EMPOL® 1038 (same as EMPOL® 1022 but less colored).

[0007] US 7,875,688 B2 describes the preparation of polyesters by the conversion of corresponding acids under acid catalysis, wherein such acids may be selected from a broad list. One of the examples describe the use of EMPOL® 1008, a mixture containing 92% dimer acids and 3% trimer acids, and about 5% fatty acid monomers.

[0008] The polyesters of the prior art however lack the necessary attributes for use in battery coatings formulations, particularly due to their poor adhesion and lack of flexibility. At elevated temperatures and at high relative humidities, strong adhesion and flexibility of battery coatings are crucial for ensuring environmental protection, preventing corrosion, maintaining electrical insulation and ensuring long-term durability.

[0009] One of the objects of the present invention is to provide a polyester compound which is well-suited for adhesives, inks or coatings, in particular coatings for batteries that operate under harsh conditions. Another of the objects of the present invention is to provide a polyester compound which may be efficiently cured and offers improved performance in formulations, particularly in terms of resistance to solvent and curing speed, while maintaining mechanical properties, such as impact resistance.BRIEF SUMMARY

[0010] In a first aspect, the present invention provides a composition comprising at least one compound of structure I:wherein:each R1is independently H or C1-C6 alkyl, preferably H or methyl;each R2is independently a residue of at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or polyepoxide;R3comprises residues of at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid and at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid, both of said diacid and triacid having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms;each R4is independently the residue of at least one ethylenically unsaturated monoacid and / or of at least one ethylenically unsaturated monoepoxide, preferably -C(=O)-;n is from 1 to 25, preferably from 1 to 10; andthe weight ratio of diacid to triacid in R3is less than 30:1, preferably the weight ratio of diacid to triacid in R3is between 30:1 and 4.1:1, more preferably between 25:1 and 4.2:1, most preferably between 20:1 and 4.3:1;wherein the composition contains less than 3 wt.%, preferably less than 2.5 wt.%, more preferably less than 2 wt.%, of a residue of a monoacid other than a residue of (meth)acrylic acid, based on the total weight of the composition.

[0011] In some embodiments, the composition of the invention comprises at least one compound of structure II:wherein:each R1is independently H or C1-C6 alkyl, preferably H or methyl;each R2is independently a residue of at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or polyepoxide;R3comprises residues of at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid and at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid, both of said diacid and triacid having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms;n is from 1 to 25, preferably from 1 to 10; andthe weight ratio of diacid to triacid in R3is less than 30:1, preferably the weight ratio of diacid to triacid in R3is between 30:1 and 4.1:1, more preferably between 25:1 and 4.2:1, most preferably between 20:1 and 4.3:1;wherein the composition contains less than 3 wt.%, preferably less than 2.5 wt.%, more preferably less than 2 wt.%, of a residue of a monoacid other than a residue of (meth)acrylic acid, based on the total weight of the composition.

[0012] In a second aspect, the present invention also provides a polyester compound which is the reaction product of:(i) at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or polyepoxide;(ii) at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid;(iii) at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid; and(iv) at least one ethylenically unsaturated monoacid and / or at least one ethylenically unsaturated monoepoxide.wherein the weight ratio of component (ii) to component (iii) is less than 30:1, preferably between 30:1 and 4.1:1, more preferably between 25:1 and 4.2:1, most preferably between 20:1 and 4.3:1; andthe reaction mixture used to obtain the polyester compound comprises less than 3% preferably less than 2.5 wt.%, more preferably less than 2 wt.%, of monoacid other than (meth)acrylic acid based on the total weight of the reactive species.

[0013] In a third aspect, the present invention provides the use of the composition or the polyester compound of the present invention in a formulation for an adhesive, a coating or an ink.

[0014] In a fourth aspect, the present invention provides the use of the composition or the polyester compound of the present invention as a constituent of a solvent-resistant encapsulant formulation, such as a coating for batteries.

[0015] In a fifth aspect, the present invention provides curable composition, comprising the composition or the polyester compound of the present invention.DETAILED DESCRIPTION

[0016] In the present application:- the term “comprise(s) a / an” should be understood as meaning “comprise(s) one or more”;- the expression “comprised between... and...” should be understood as including the limits; - unless mentioned otherwise, the wt.% (or % by weight) in a compound or composition is expressed based on the total weight of the compound or composition, respectively;- any description, even though described in relation to a specific embodiment, is applicable to and interchangeable with other embodiments of the present invention;- the term, “independently” or “independently selected” with respect to choices of groups in a structure, means that if multiple groups are present in the structure, they do not need to be identical; instead, each group can be selected from the listed options independently of the others; for example, the recitation, “R2is independently a residue of at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol or diepoxide” means that one R2in a structure may be an aliphatic diol and another may be an aryl diepoxide.- where an element or component is said to be included in and / or selected from a list of recited elements or components, it should be understood that in related embodiments explicitly contemplated here, the element or component can also be any one of the individual recited elements or components, or can also be selected from a group consisting of any two or more of the explicitly listed elements or components; any element or component recited in a list of elements or components may be omitted from such list; and- any recitation herein of numerical ranges by endpoints includes all numbers subsumed within the recited ranges as well as the endpoints of the range and equivalents.Definitions

[0017] The term “(meth)acrylate group” as used herein refers to an acrylate group or a methacrylate group. An acrylate group corresponds to an acryloyl group of formula -C(=O)-CH=CH2. A methacrylate group corresponds to a methacryloyl group of formula -C(=O)-C(CH3)=CH2.

[0018] The term “curable” or “curable polyester” as used herein refers to a compound or a polyester compound comprising at least one ethylenic unsaturation, i.e., at least one polymerizable carbon-carbon double bond, in particular at least one carbon-carbon double bond capable of participating in a free radical polymerization wherein at least one of the carbon atoms of the double bond becomes covalently bonded to another atom, in particular a carbon atom, in a second molecule. The ethylenic unsaturation may for example be present as part of an a,|3-unsaturated carbonyl moiety, e.g., an a,|3-unsaturated ester moiety such as an acrylate functional group ( — O-C(O)-CH=CH2) or a methacrylate functional group ( — O-C(O)-C(CH3)=CH2); an a,|3-unsaturated amide moiety such as an acrylamide functional group ( — NH-C(O)-CH=CH2) or a methacrylamide functional group ( — NH-C(O)-C(CH3)=CH2); a vinyl group ( — CH=CH2); a vinyl ether group ( — O-CH=CH2); an allyl group ( — CH2-CH=CH2); or an allyl ether group ( — O-CH2-CH=CH2). Among others, the ethylenic unsaturation may for example be a residue of any of the following acids: acrylic acid, methacrylic acid, itaconic acid, fumaric acid, maleic acid or mixtures thereof. The ethylenic unsaturation may also be a residue of any of the following monoepoxides: glycidyl acrylate, glycidyl methacrylate, allyl glycidyl ether, acrylic acid glycidyl ether, methacrylic acid glycidyl ether or mixtures thereof.

[0019] The term “(meth)acrylated” or “(meth)acrylated polyester” as used herein refers to a compound or a polyester compound comprising at least one (meth)acrylate group as defined herein. A (meth)acrylated polyester therefore qualifies as a curable polyester as defined herein.

[0020] The term “unsaturated” as used herein means comprising one or more double or triple carbon-carbon bonds, in particular one or more double carbon-carbon bonds. The term “ethylenically unsaturated” as used herein means comprising two double bonds separated by a carbon-carbon single bond.

[0021] The term “residue” as used herein refers to the group of atoms remaining in a product after the removal of the functional groups that react to form linkages with another compound. For example, the residue of a diol with the structure HO-R4-OH is understood to be R4.

[0022] The term “saturated” as used herein means not comprising any double or triple carboncarbon bonds.

[0023] The term “aliphatic” as used herein refers to non-aryl and encompasses non-aromatic rings (e.g., a cycloaliphatic ring). It may be linear or branched, saturated or unsaturated, cyclic or acyclic. An aliphatic ligand may be substituted by one or more groups, for example selected from alkyl, hydroxyl, halogen (Br, Cl, I), isocyanate, carbonyl (=0), amine, carboxylic acid, -C(=O)-OR’, -C(=O)-O-C(=O)-R’, each R’ being independently a C1-C6 alkyl. It may comprise one or more bonds selected from ether, ester, amide, urethane, urea, carbonate, organosiloxane, and mixtures thereof.

[0024] The term “C1-C6” as used herein refers to the number of carbon atoms comprised in a specific group or linker. For example, a C1-C6 alkyl is an alkyl comprising from 1 to 6 carbon atoms.

[0025] The term “aryl” as used herein means comprising an optionally substituted polyunsaturated aromatic group. The aryl may contain a single ring (i.e. phenyl) or more than one ring wherein at least one ring is aromatic. When the aryl comprises more than one ring, the rings may be fused or linked via a direct bond (for example biphenyl). The aromatic ring may optionally comprise one to two additional fused rings (i.e. cycloalkyl, heterocycloalkyl or heteroaryl). Examples include phenyl, naphtyl, biphenyl, phenanthrenyl and naphthacenyl.

[0026] The term “heteroaryl” as used herein means comprising an optionally substituted polyunsaturated aromatic group wherein one or more of the ring atoms is a heteroatom such as O, N and S.

[0027] The term “aralkyl” as used herein refers to an aryl substituted by an alkyl group. An example of an aralkyl group is tolyl.

[0028] The term “alkaryl” as used herein refers to an alkyl substituted by an aryl group. An example of an alkaryl group is benzyl (-CH2-Phenyl).

[0029] The term “heteroaralkyl” as used herein refers to an aralkyl group in which the aryl contains at least one heteroatom, such as O, N or S.

[0030] The term “alkheteroaryl” as used herein refers to an heteroaryl group substituted by an alkyl.

[0031] Molecular weights herein are number averaged (Mn), weight averaged (Mw), or z-averaged molecular weights measured using gel permeation chromatography (GPC) with polystyrene standards, unless stated otherwise.Composition comprising compound I or II

[0032] The present invention relates to a composition comprising a polyester compound.

[0033] The polyester compound described herein, present in the composition of the present invention, comprises different segments: segments comprising ester bonds and segments comprising ethylenic unsaturations. Differently said, the compound of the present invention comprises several ester functions in its backbone and is functionalized with groups comprising at least one ethylenic unsaturation. Based on these functionalities, the compound of the present invention may be qualified as a polyester compound. Such polyester compound is also called interchangeably “compound”, “polyester compound”, “oligomer” or “polyester oligomer”.

[0034] More precisely, the polyester compound in the composition of the present invention has the structure I:wherein:each R1is independently H or C1-C6 alkyl, preferably H or methyl;each R2is independently a residue of at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or polyepoxide;R3comprises residues of at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid and at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid, both of said diacid and triacid having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms;each R4is independently the residue of at least one ethylenically unsaturated monoacid and / or of at least one ethylenically unsaturated monoepoxide, preferably -C(=O)-;n is from 1 to 25, preferably from 1 to 10;the weight ratio of diacid to triacid in R3is less than 30:1, preferably the weight ratio of diacid to triacid in R3is between 30:1 and 4.1:1, more preferably between 25:1 and 4.2:1, most preferably between 20:1 and 4.3:1;wherein the composition contains less than 3 wt.%, preferably less than 2.5 wt.%, more preferably less than 2 wt.%, of a residue of a monoacid other than (meth)acrylic acid, based on the total weight of the composition.

[0035] In some embodiments, the composition of the present invention comprises a polyester compound of structure II:wherein:each R1is independently H or C1-C6 alkyl, preferably H or methyl;each R2is independently a residue of at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or polyepoxide;R3comprises residues of at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid and at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid, both of said diacid and triacid having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30, carbon atoms;n is from 1 to 25; andthe weight ratio of diacid to triacid in R3is less than 30:1, preferably the weight ratio of diacid to triacid in R3is between 30:1 and 4.1:1, more preferably between 25:1 and 4.2:1, most preferably between 20:1 and 4.3:1;wherein the composition contains less than 3 wt.%, preferably less than 2.5 wt.%, more preferably less than 2 wt.%, of a residue of a monoacid other than a residue of (meth)acrylic acid, based on the total weight of the composition.

[0036] The inventors have determined that for the composition of the present invention to achieve the required technical requirements of solvent resistance and fast curing speed, while preserving its mechanical properties, at least two technical limitations are imposed on the components involved in the preparation of the composition. First, the weight ratio of diacid to triacid in compound of structure I or II (also called compound I or II herein) must be selected to be less than 30: 1. Additionally, the composition must contain less than 3 wt.% of residues of a monoacid other than a residue of (meth)acrylic acid based on the total weight of the composition. The selection of the components involved in the preparation of the composition of the present invention is crucial in order to meet these two technical features.

[0037] In particular, it has been found that the use of the compositions of the present invention not only provides a better resistance to solvent to formulations comprising them (e.g., coatings), in comparison to the use of certain polyesters described in the prior art, but the use of such compositions also provides a better cure speed to formulations incorporating them. Without being bound to any theory, it appears that the adjustment of the levels of monoacids and triacids in the compositions of the present invention introduce enough of a crosslink density to boost the cure speed, without impacting the solvent resistance of formulations incorporating the compositions of the present invention. Additionally, while faster cure speed is generally known to cause a decrease in the coatingmechanical performances, such as impact resistance, the mechanical performance of the coatings incorporating the compositions of the present invention are not adversely impacted.

[0038] The polyester compound described herein is curable, meaning that it can undergo crosslinking under specific conditions. Consequently, the composition of the present invention transforms from a liquid or semi-liquid state into a solid or semi-solid state when exposed to certain conditions, such as light, heat, and / or in the presence of a curing agent.

[0039] More precisely, the composition of the present invention may be efficiently cured when exposed to actinic radiation (such as UV, near-UV, visible, infrared, near-infrared and / or electron beam radiation) and / or heat, optionally in the presence of a free radical initiator and / or a cationic initiator.

[0040] Before being cured, the compositions of the present invention may be incorporated into a formulation, for example a coating, adhesive, or ink formulation. Upon polymerization or curing, the composition of the invention may become incorporated in a polymerized matrix or polymeric chain, for example in adhesives, inks and coatings.

[0041] The cured compositions obtained from curable composition incorporating the compositions of the present invention exhibit mechanical properties particularly well-suited for adhesives, inks and coatings, in particular battery coatings. These properties enable the coatings to withstand the harsh operating conditions of batteries, such as exposure to electrolytes, elevated temperatures, and repeated charge-discharge cycles, while maintaining adhesion, flexibility, and chemical resistance.

[0042] One essential feature of the composition of the present invention is that it comprises a polyester compound according to structure I or II, wherein the weight ratio of diacid to triacid in R3is less than 30:1. Preferably, the weight ratio of diacid to triacid in R3is between 30:1 and 4.1:1; more preferably, the weight ratio of diacid to triacid in R3is between 25:1 and 4.2:1; most preferably, the weight ratio of diacid to triacid in R3is between 20: 1 and 4.3:1.

[0043] Another essential feature of the composition of the present invention is that it contains less than 3 wt.% of a residue of a monoacid other than a residue of (meth)acrylic acid, based on the total weight of the composition. Preferably, the composition of the present invention contains less than 2.5 wt.% of a residue of a monoacid other than a residue of (meth)acrylic acid; more preferably, it contains less than 2 wt.%; most preferably, it contains less than 1.8%, less than 1.5%, less than 1.2%, less than 1 wt.%, less than 0.9% or even less than 0.5 wt.%, of a residue of a monoacid other than a residue of (meth)acrylic acid based on the total weight of the composition. The total weight of the composition may correspond to the total weight of the reactive species used to prepare the polyester compound (i.e. the total weight of acids, alcohols and epoxides used to prepare the polyester compound).

[0044] In a preferred embodiment, the composition of the present invention contains less than 3 wt.%, preferably less than 2.5 wt.%, most preferably less than 1.8%, less than 1.5%, less than 1.2%, less than 1 wt.%, less than 0.9% or even less than 0.5 wt.%, of a residue of a monoacid having at least 10, preferably at least 12, more preferably at least 14, more preferably at least 16, and most preferably at least 18, carbon atoms. Said residue of a monoacid may be saturated or unsaturated, preferably unsaturated. The total weight of the composition may correspond to the total weight of the reactive species used to prepare the polyester compound (i.e. the total weight of acids, alcohols and epoxides used to prepare the polyester compound).

[0045] One of the segments in the compound of structure I and II of the composition of the present invention is a residue of at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or polyepoxide. Such residue is represented as R2in structures I and II herein.

[0046] The diol, polyol, diepoxide and polyepoxide used to prepare the compound of structure I and II are not intended to be limited to specific structures only. The term “polyol” as used herein refers to any compound comprising at least two (two or more) hydroxyl groups, in its broadest meaning. The term “diol” as used herein refers to any compound comprising two hydroxyl groups, in its broadest meaning. The term “polyepoxide” as used herein refers to any compound comprising at least two (two or more) epoxy groups ( ° ), in its broadest meaning. The term “diepoxide” as used herein refers to any compound comprising two epoxy groups ( ° ), in its broadest meaning.

[0047] In some embodiments, each R2is independently a residue of at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol or diepoxide.

[0048] Preferably, each R2in structures I or II is independently a residue of an acyclic diol or polyol, an aryl diol or polyol, an aryl polyepoxide or diepoxide, or a component comprising at least two glycidyl ether functions, for example, two, three or four glycidyl ether functions.

[0049] In particular, R2may be the residue of a diprimary diol. The term “diprimary diol” herein refers to an alcohol comprising containing two primary alcohol groups (-CH2OH). The primary diol may for example be 1,4-butanediol, ethylene glycol, 1,6-hexanediol, 1,8-octanediol or a mixture thereof.

[0050] In particular, R2may comprise or be substituted with at least one ester group, at least one alkoxylate group or both. In some embodiments, R2comprises or is substituted with one ester group only.

[0051] In particular, R2may be the residue of an acyclic polyol, preferably an acyclic diol. In particular, R2may be the residue of a linear or branched aliphatic polyol or diol, preferably a linearor branched aliphatic diol. For example, R2may be the residue of a diol selected among alkyl diols (or alkyl glycols), alkoxylated alkyl diols, polyether diols, neopentyl glycols, alkylated neopentyl glycols, and alkoxylated neopentyl glycols. More particularly, the acyclic diol may be selected from the group consisting of propanediols (e.g., 1,2-propoanediol or 1,3 -propanediol), butanediols (e.g., 1,4-butanediol), pentanediols (e.g., 1,5 -pentanediol), hexanediols (e.g., 1,6-hexanediol), octanediols, decanediols, dodecanediols, 2-methy 1-1, 3 -propanediol, 2-methyl-2,4-pentanediol, and neopentyl glycol and mixtures thereof. The acyclic diol may be selected from the group consisting of ethoxylated alkyl diols, propoxylated alkyl diols, ethoxylated neopentyl glycol, propoxylated neopentyl glycol, and mixtures thereof. The acyclic diol may an alkylated neopentyl glycol, for example neopentyl monohydroxy pivalate (HPN glycol), also called neopentyl glycol mono(hydroxypivalate). The acyclic diol may a polyether diol, for example be selected from the group consisting of polyethylene oxide), polypropylene oxide), poly(butylene oxide) and mixtures thereof.

[0052] In particular, R2may be the residue of an aryl polyol or an aryl diol, preferably an aryl diol. More particularly, the aryl diol may be selected from the group consisting of hydroquinone (HQE), alkoxylated HQE (for example, ethoxylated HQE and propoxylated HQE), bisphenol-A (BP A), alkoxylated BPA (for example ethoxylated bisphenol A and propoxylated bisphenol A), propoxylated BPA, and bis-ethylene glycol terephthalate.

[0053] In particular, R2may comprise a first residue of a first substituted or unsubstituted aliphatic, aryl, or heteroaryl diol and a second residue of a second diol selected from the group consisting of tricyclodecanedimethanol, cyclohexane dimethanol, hydrogenated bisphenol A and hydrogenated bisphenol F, wherein the second diol is present in an amount of not more than 45 mol.% of the total diol content.

[0054] In particular, R2may be the residue of an aryl polyepoxide or an aryl diepoxide, preferably an aryl diepoxide. The aryl diepoxide may be selected from the group consisting of bisphenol A diglycidyl ether (BADGE), bisphenol F diglycidyl ether (BFDGE), bisphenol S diglycidyl ether (BPSGE), and mixtures thereof.

[0055] In particular, R2may be the residue of a diepoxide or poly epoxide or a component comprising at least two glycidyl ether functions. More particularly, the diepoxide may be selected from the group consisting of alkyl diol diglycidyl ether (e.g., 1,4-butanediol diglycidyl ether), aryl diol diglycidyl ether (e.g., hydrogenated bisphenol A diglycidyl ether), and polyether diol diglycidyl ether (e.g., dipropylene glycol diglycidyl ether). Additionally, the diepoxide may be the neopentyl glycol diglycidyl ether. The diepoxide, optionally polyepoxide, may be selected from 1, 2,3,4-diepoxy butane; 1,2,4,5-diepoxypentane; 1,2,5,6-diepoxyhexane; 1,2,7,8-diepoxyoctane; 1,2,9,10-diepoxy decane; bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, brominated bisphenol A diglycidyl ether, brominated bisphenol F diglycidyl ether, brominatedbisphenol S diglycidyl ether, epoxy novolak resin, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, hydrogenated bisphenol S diglycidyl ether, 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane-l,4-dioxane, bis(3,4-epoxycyclohexylmethyl)adipate, vinylcyclohexene oxide, 4-vinylepoxycyclohexane, bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate, 3,4-epoxy-6-methylcyclohexyl-3',4'-epoxy-6'-methylcyclohexanecarboxylate, methylenebis(3,4-epoxycyclohexane), dicyclopentadiene diepoxide, di(3,4-epoxycyclohexylmethyl) ether of ethylene glycol, ethylenebis(3, 4-epoxycyclohexanecarboxylate), ethylene glycol diglycidyl ether, 1,2- or 1,3-propylene glycol diglycidyl ether, 1,2-, 1,3- or 1,4-butanediol diglycidyl ether, 1,5 -pentanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,7-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1,9-nonanediol diglycidyl ether, 1,10-decanediol diglycidyl ether, 1,12-dodecanediol diglycidyl ether, 2 -methyl- 1,3 -propanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 2, 2-diethyl- 1,3 -propane diol diglycidyl ether, 3 -methyl- 1,5 -pentanediol diglycidyl ether, 3,3-dimethyl-l,5-pentanediol diglycidyl ether, 2, 4-diethy 1-1, 5 -pentanediol diglycidyl ether, 3,3-butylethyl-l,5-pentane diol diglycidyl ether, di-, tri- or tetra(ethylene glycol) diglycidyl ether, di-, tri- or tetra(l,2-propylene glycol) diglycidyl ether, di-, tri- or tetra(l,3-propylene glycol) diglycidyl ether, di-, tri- or tetra(l,4-butylene glycol) diglycidyl ether, a polyethylene glycol) diglycidyl ether, a polypropylene glycol) diglycidyl ether, a poly(trimethylene glycol) diglycidyl ether, a poly(tetramethylene glycol) diglycidyl ether, a polyethylene glycol-co-propylene glycol) diglycidyl ether, glycerol triglycidyl ether, a polyglycerol polyglycidyl ether, trimethylolmethane triglycidyl ether, trimethylolethane triglycidyl ether, trimethylolpropane triglycidyl ether, di(trimethylolpropane) tetraglycidyl ether, pentaerythritol tetraglycidyl ether, diglycidyl cyclohexanedicarboxylate, cyclohexane diglycidyl ether, cyclohexane- 1,4-dimethanol diglycidyl ether, tricyclodecane dimethanol diglycidyl ether, isosorbide diglycidyl ether, pyrocatechol diglycidyl ether, resorcinol diglycidyl ether, cardol diglycidyl ether, phloroglucinol triglycidyl ether, pyrogallol triglycidyl ether, tris(hydroxyphenyl)methane triglycidyl ether, tris(hydroxyphenyl)ethane triglycidyl ether, diglycidyl phthalate, diglycidyl terephthalate, diglycidyl isophthalate, polyglycidyl ethers of a polyether polyol obtained by the addition of one or more alkylene oxides to an aliphatic polyhydric alcohol such as ethylene glycol, propylene glycol, and glycerol, diglycidyl esters of aliphatic long-chain (C6-C22) dibasic acids, monoglycidyl ethers of aliphatic higher alcohols, monoglycidyl ethers of phenol, cresol, butyl phenol, or polyether alcohols obtained by the addition of alkylene oxide to these compounds, glycidyl esters of higher fatty acids, an epoxidized vegetable oil (such as epoxidized soybean oil and epoxidized linseed oil), epoxybutylstearic acid, epoxyoctylstearic acid, epoxidized polybutadiene, triglycidyl isocyanurate and the like.

[0056] In a preferred embodiment, each R2is independently selected from the residue of a diol or a polyol having at least 3 OH groups. In particular, each R2may independently be selected from theresidue of a diol or a polyol having 3 to 6 OH groups. More particularly, each R2may independently be selected from the residue of a diol or a polyol having 3 or 4 OH groups.

[0057] In a preferred embodiment, each R2is independently selected from the residue of a diol or part of the R2groups are independently selected from the residue of a diol and the remaining part of the R2groups are selected from the residue of a polyol having at least 3, in particular 3 to 6, more particularly 3 or 4, OH groups.

[0058] When R2is the residue of a diol, it may correspond to the following formula (1) and when R2is the residue of a polyol having at least 3 OH groups, it may correspond to the following formula (2a) or (2b):whereinR1and R4are as defined above;each A is independently an aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl divalent moiety,each P is independently an aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl (x+2) valent moiety;each x is independently at least 1, in particular from 1 to 4, more particularly 1 or 2.

[0059] In formula (1), A may be a divalent moiety comprising from 1 to 50 carbon atoms and optionally one or more heteroatoms independently selected from O, N and S. In particular, A may be a divalent moiety according to any one of formulae (3) to (14):-(CR4R’4)e- (3)-CH2-O-CH2- (4)-(CR9R’9)m-[OC(=O)-(CR8R’8)k]i- (8)-[(CRioR’io)n-0-C(=0)-(CRiiR’ii)o-C(=0)-0]P-(CRioR’io)n- (9)-(CRi2R’i2)q-C(=O)-O-(CRi3R’i3)r-O-C(=O)-(CRi2R’i2)q- (10)-(CRi4R’i4)s-Cy-[Lo-Cy]t-(CRi4R’i4)s- (11)-(CRi4R’i4)s-O-Cy-O-(CRi4R’i4)s- (12)-(CRi4R’i4)s-O-C(=O)-Cy-C(=O)-O-(CRi4R’i4)s- (13)- each R5, R’s, Re, R’e, Rs, R’s, R15 and R’15 is independently H or methyl;- each W is independently -O- or -S-;- each Cy is independently an optionally substituted ring or polycyclic ring system, in particular an optionally substituted cyclopentylene, cyclohexylene, phenylene, naphthylene, bicyclooctylene or tricyclodecylene;- each Lois independently a bond or a linker such as Aik, -C(=O)-, -C(=O)-O-Alk-O- C(=O)-, -SO-, -SO2-, -C(=CCl2)- and -Alk-Ph-Alk-;- Aik is an optionally substituted alkylene;- Ph is an optionally substituted phenylene;- each e, j, m, n, o and r is independently an integer from 2 to 20;- each s is independently an integer from 0 to 20;- each s’ is independently an integer from 1 to 20;- each f, h and u is independently an integer from 2 to 4;- t is an integer equal to 0 or 1;- each g, 1, p and q is independently an integer from 1 to 20;- each v is independently an integer from 0 to 10, in particular from 1 to 6;- each i is independently an integer from 0 to 20 with the proviso that at least one i is not 0;- k is an integer from 3 to 12.

[0060] In formulae (2a) and (2b), P may be a (x+2)valent moiety comprising from 1 to 50 carbon atoms and optionally one or more heteroatoms independently selected from O, N and S. In particular, P may be selected from:- a trivalent moiety according to any one of formulae (15) to (20):wherein:each R15and R16is independently a linear or branched alkylene;each Ru and R’n is independently H or methyl;- each Ris and R’is is independently H, alkyl or alkoxy, preferably each RI8and R’is is alkyl;- each R19 is independently a linear or branched alkylene;- Rf is H or methyl;- w is an integer equal to 0 or 1;- each a’ is independently an integer from 0 to 2 with the proviso that not more than one a’ is equal to 0, preferably each a’ is equal to 1 or one a’ is equal to 0 and the two other a’ are equal to 1;- each a’ ’ is independently an integer from 0 to 2 with the proviso that not more than one a” is equal to 0, preferably each a” is equal to 1 or one a” is equal to 0 and the two other a” are equal to 1;- each b’ is independently an integer from 2 to 4, in particular 2;- each c’ is independently an integer from 0 to 10, in particular from 1 to 6;a tetravalent moiety according to any one of formulae (21) to (24):(23)wherein:- each R2o, R’20, R22 and R’22 is independently H or methyl;- each R21 and R25 is independently a linear or branched alkylene;- each R23 and R24 is independently H, alkyl or alkoxy, preferably alkyl;- each d’ is independently an integer from 0 to 2 with the proviso that not more than one d’ is equal to 0, preferably each d’ is equal to 1;- each d’ ’ is independently an integer from 0 to 2 with the proviso that not more than one d” is equal to 0, preferably each d” is equal to 1;- each e’ and g’ is independently an integer from 2 to 4, in particular 2;- each f ’ and h’ is independently an integer from 0 to 10, in particular from 1 to 6; - a tetra-, penta- or hexavalent moiety according to formula (25):wherein:- each R26and R’26 is independently H or methyl;- each i’ is independently an integer from 2 to 4, in particular 2;- each j ’ is independently an integer from 0 to 10, in particular from 1 to 6;- k’ is an integer from 1 to 3;- a tri-, tetra-, penta- or hexavalent moiety according to formula (26):wherein- each Rgis independently selected from H, alkyl, cycloalkyl, aryl, alkaryl, aralkyl, alkoxy, -C(=O)O-Alkyl and a halogen atom;- k” is an integer from 1 to 4;- a hexavalent moiety according to any one of formulae (27) to (29):(29) wherein- each R27, R’27, R29 and R’29 is independently H or methyl;- each R28is independently a linear or branched alkylene;- each 1’ and n’ is independently an integer from 2 to 4, in particular 2;- each m’ and o’ is independently an integer from 0 to 10, in particular from 1 to 6.

[0061] In a preferred embodiment, each R2is independently selected from:- the residue of a cyclic diol, in particular the residue of a cyclic diol selected from hydroquinone (HQE), hydroquinone bis(2 -hydroxy ethyl) ether (HQEE), bisphenol-A, B, F or S, bis-ethylene glycol terephthalate, pyrocatechol, resorcinol, cardol, cyclohexanediol, cyclohexane dimethanol, norbornene dimethanol, norbornane dimethanol, tricyclodecanediol, tricyclodecanedimethanol,dicyclopentadiene diol, hydrogenated bisphenol-A, B, F or S, a dianhydrohexitol (i.e. isosorbide, isomannide, isoidide), as well as the alkoxylated (e.g. ethoxylated and / or propoxylated) derivatives thereof and mixtures thereof; or- the residue of a diol comprising an ester bond, in particular the residue of neopentyl glycol mono(hydroxypivalate) having the following structure:

[0062] In another preferred embodiment, part of the R2groups are independently selected from the residue of a diol and the remaining part of the R2groups are independently selected from the residue of a polyol having at least 3 OH groups, in particular 3 to 6 OH groups, more particularly 3 or 4 OH groups. The molar ratio of residues derived from the diol to residues derived from the polyol having at least 3 OH groups may be from 1 to 50, preferably from 2 to 25, more preferably from 5 to 20. In particular, part of the R2groups may independently be selected from the residue of a diol selected from ethylene glycol, propanediols (e.g., 1,2-propanediol or 1,3 -propanediol), butanediols (e.g., 1,2-, 1,3- or 1,4-butanediol), pentanediols (e.g., 1,5 -pentanediol), hexanediols (e.g., 1,6-hexanediol), octanediols, decanediols, dodecanediols, 2 -methyl- 1,3 -propanediol, 2-methyl-2,4-pentanediol, neopentyl glycol, 2, 2-diethy 1-1, 3 -propanediol, 3 -methyl- 1,5 -pentanediol, 3,3-dimethyl-1,5 -pentanediol, 2,4-diethyl-l,5-pentanediol, 3,3-butylethyl-l,5-pentane diol, neopentyl glycol mono(hydroxypivalate), di-, tri- or tetra(ethylene glycol), di-, tri- ortetra(l,2-propylene glycol), di-, tri- or tetra( 1,3 -propylene glycol), di-, tri- or tetra(l,4-butylene glycol), a polyethylene glycol), a polypropylene glycol), a poly (trimethylene glycol), a poly (tetramethylene glycol), a polyethylene glycol-co-propylene glycol, hydroquinone (HQE), hydroquinone bis(2 -hydroxyethyl) ether (HQEE), bisphenol-A, B, F or S, bis-ethylene glycol terephthalate, pyrocatechol, resorcinol, cardol, cyclohexanediol, cyclohexane dimethanol, norbomene dimethanol, norbomane dimethanol, tricyclodecanediol, tricyclodecanedimethanol, dicyclopentadiene diol, hydrogenated bisphenol-A, B, F or S, a dianhydrohexitol (i.e. isosorbide, isomannide, isoidide), as well as the alkoxylated (e.g. ethoxylated and / or propoxylated) derivatives thereof and mixtures thereof. In particular, the remaining part of the R2groups may independently be selected from the residue of a polyol having at least 3 OH groups selected from trimethylolmethane, trimethylolethane, trimethylolpropane, di(trimethylolpropane), triethylolpropane, pentaerythritol, dipentaerythritol), tripentaerythritol), glycerol, di-, tri- or tetraglycerol, a poly glycerol, an alditol (i.e. erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galactitol, fucitol or iditol), tris(2-hydroxyethyl)isocyanurate, phloroglucinol, pyrogallol, tris(hydroxyphenyl)methane, tris(hydroxyphenyl)ethane, as well as the alkoxylated (e.g. ethoxylated and / or propoxylated) derivatives thereof and mixtures thereof.

[0063] One of the segments in the compound of structure I and II of the composition of the present invention comprises residues of a) at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid and b) at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid, wherein both of said diacid and triacid have at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms. Such residue is represented as R3in structures I and II. As used herein, the term R3comprises residues of at least one diacid and at least one triacid may be understood as part of the R3groups independently comprise the residue of a diacid and part of the R3groups independently comprise the residue of a triacid. Such a distribution can be obtained by using a mixture of a diacid and a triacid to obtain the compounds of structure I and II. In some specific examples, the diacid has 36 carbon atoms and the triacid has 54 carbon atoms. Such diacid and triacid may be commercialized as a mixture. Reference can notably be made to UNIDYME™ 18 from KRATON, long chain (C36) acid mixture containing about 17% trimer acids and about 1.5% monomer acids.

[0064] In particular, R3may comprise residues of a diacid having its COOH groups in alpha position of methylene (-CH2-) groups.

[0065] In particular, R3may comprise residues of a substituted or unsubstituted phenyl or naphthyl diacid and / or triacid, preferably of both substituted or unsubstituted phenyl or naphthyl diacid and triacid.

[0066] In particular, R3may comprise residues of a substituted or unsubstituted norbomenyl diacid and / or triacid, preferably of both substituted or unsubstituted norbornenyl diacid and triacid.

[0067] In particular, R3may comprise residues of a substituted or unsubstituted non-hydrogenated diacid and / or triacid, preferably of both substituted or unsubstituted non-hydrogenated diacid and triacid.

[0068] In a preferred embodiment, R3may comprise a residue of a fatty acid dimer and a residue of a fatty acid trimer. In particular, R3may comprise a residue of a non-hydrogenated fatty acid dimer and a residue of a non-hydrogenated fatty acid trimer.

[0069] In a preferred embodiment, part of the R3groups are independently according to the following formula (30) and the remaining part of the R3groups are independently according to the following formula (31a) or (31b):R1, R2and R4are as defined above;D is a substituted or unsubstituted aliphatic, aryl, or heteroaryl divalent moiety having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms;T is a substituted or unsubstituted aliphatic, aryl, or heteroaryl trivalent moiety having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms.

[0070] In formula (30), D preferably corresponds to the residue obtained by removing the COOH groups of a fatty acid dimer.

[0071] In formulae (3 la) and (3 lb), T preferably corresponds to the residue obtained by removing the COOH groups of a fatty acid trimer.

[0072] Fatty acid dimers and trimers may be obtained by oligomerization (in particular by dimerization or trimerization) of a fatty acid. According to the present invention, a fatty acid is an acid having a fatty chain, i.e., a hydrocarbyl (non-cyclic) chain comprising from 10 to 30, in particular 12 to 26, more specifically 14 to 20, consecutive carbon atoms. A fatty acid can be saturated or unsaturated. A saturated fatty acid is a fatty acid that does not include a C=C double bond. An unsaturated fatty acid includes at least one C=C double bond. A monounsaturated fatty acid contains a single C=C double bond. A polyunsaturated fatty acid contains more than one C=C double bond. A polyunsaturated fatty acid can be conjugated or unconjugated. The hydrocarbyl chain of a fatty acid can be substituted, in particular by one or more hydroxyl, epoxide or carbonyl functions. The term "fatty acid" includes fatty acid precursors, i.e. compounds that can generate a fatty acid in situ, in particular by hydrolysis, such as fatty acid esters, including C1-C4 alkyl esters of fatty acids.

[0073] The oligomerization of fatty acids can be carried out in particular from unsaturated fatty acids and / or from fatty acids functionalized by a hydroxyl or epoxide function. Thus, two molecules of unsaturated fatty acids can react by Diels-Alder reaction to form one or more rings. Alternatively, two molecules of unsaturated fatty acids can react by radicular addition to form a covalent bondbetween the fatty chains. Alternatively, the hydroxyl function of a hydroxylated fatty acid can react with the acid function of a fatty acid to form an ester bond between the two molecules. Alternatively, the acid function of a fatty acid can react with the epoxide function of an epoxidized fatty acid to form an ester function between the two molecules.

[0074] The fatty acid dimer can be a fatty acid dimer having 32 to 40, preferably 34 to 38, more preferably 36 carbon atoms. Such a compound can be obtained by dimerization of fatty acids having 16 to 20, preferably 17 to 19, more preferably 18 carbon atoms. The fatty acid dimer can be an unsaturated fatty acid dimer, also known as a non-hydrogenated fatty acid dimer.

[0075] The fatty acid trimer can be a fatty acid trimer having 48 to 60, preferably 51 to 57, more preferably 54 carbon atoms. Such a compound can be obtained by trimerization of fatty acids having 16 to 20, preferably 17 to 19, more preferably 18 carbon atoms. The fatty acid trimer can be an unsaturated fatty acid trimer, also known as a non-hydrogenated fatty acid trimer.

[0076] The polyester compound of the present invention comprises segments comprising ethylenic unsaturations. Such residue contributes to radical R1and R4in structure I, and R1in structure II.

[0077] According to the present invention, the compounds of structures I or II are such that each R1is independently H or C1-C6 alkyl; preferably, each R1is independently H or methyl.

[0078] According to the present invention, the compound of structures I is such that each R4is independently the residue of at least one ethylenically unsaturated monoacid and / or of at least one ethylenically unsaturated monoepoxide; preferably, each R4is -C(=O)-.

[0079] In particular, the ethylenically unsaturated monoacid may be at least one of acrylic acid, methacrylic acid, an acryloyl halide (such as acryloyl chloride), a methacryloyl halide (such as methacryloyl chloride), acrylic anhydride, methacrylic anhydride or mixtures thereof; preferably acrylic acid, methacrylic acid, or mixtures thereof.

[0080] In particular, the ethylenically unsaturated monoepoxide may be at least one of glycidyl acrylate, glycidyl methacrylate, allyl glycidyl ether, acrylic acid glycidyl ether, methacrylic acid glycidyl ether or mixtures thereof.

[0081] The ethylenically unsaturated monoacid and / or monoepoxide may for example be (meth)acrylic acid, glycidyl (meth)acrylate, and the reaction products of hydroxy(alkyl) (meth)acrylates with phthalic or succinic anhydride or acid. Hydroxyalkyl (meth)acrylates include 4-hydroxybutyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate. The adducts with succinic and phthalic acid with 2-hydroxyethyl (meth)acrylate are commercially available as CN146 (HEA monophthalate), CN147 (HEA monosuccinate), and CN149 (HEMA monophthalate) from Sartomer.

[0082] In particular, the composition of the present invention may be such as to comprise at least 51 mol.% of compound I or II where R1is H, preferably at least 60 mol.%, at least 70 mol.%, at least 80 mol.% or at least 85 mol.%, based on the total number of moles of compound I or II in the composition.

[0083] Compound I or II may be such that it has a number average molecular weight (Mn) of at least about 750 g / mol, preferably between about 1,000 and about 15,000 g / mol, between about 1,250 and about 10,000 g / mol, or between about 1,500 and about 7,000 g / mol.

[0084] Compound I or II may be such that it has a weight average molecular weight (Mw) of at least about 1,000 g / mol, preferably between about 2,000 and about 30,000 g / mol, between about 3,000 and about 20,000 g / mol, or between about 3,500 and about 15,000 g / mol.

[0085] Compound I or II may be such that it has a polydispersity index (D) of less than 3, preferably less than 2.5 or more preferably less than 2.

[0086] Number averaged (Mn), weight averaged (Mw), or Z-averaged (Mz) molecular weights may be measured using gel permeation chromatography (GPC) with polystyrene standards. Polydispersity index (D) may be calculated as Mw / Mn.Polyester compound as a reaction product

[0087] The polyester compound of the present invention may be the reaction product of four distinct components, as detailed herein.

[0088] The polyester compound of the present invention is produced with lower energy requirements than polyurethanes and utilizes components that pose fewer safety hazards.

[0089] The polyester compound of the present invention may be the reaction product of:(i) at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or poly epoxide;(ii) at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid;(iii) at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid; and(iv) at least one ethylenically unsaturated monoacid and / or at least one ethylenically unsaturated monoepoxide;wherein the weight ratio of component (ii) to component (iii) is less than 30:1, preferably between 30:1 and 4.1:1 more preferably between 25:1 and 4.2:1, most preferably between 20:1 and 4.3:1; and the reaction mixture used to obtain the polyester compound comprises less than 3% preferably less than 2.5 wt.%, more preferably less than 2 wt.%, of monoacid other than (meth)acrylic acid based on the total weight of the reactive species.

[0090] According to a first embodiment, components (i)-(iv) may be mixed together with no specific order of addition.

[0091] The resulting polyester compound may thus be the reaction product of a one-stage process.

[0092] In this first embodiment, a condensation reaction of components (i)-(iv) may be catalyzed by a strong protic acid, such as methane sulfonic acid, p-toluene sulfonic acid, or sulfuric acid. The reaction may carried out with byproduct water continuously removed (e.g., by means of reflux and condensation into a sidearm).

[0093] In a second embodiment, a polyester may first be prepared by reacting components (i)- (iii), then such polyester may be reacted with component (iv) to provide the polyester compound of the present invention.

[0094] The resulting polyester compound may thus be the reaction product of a two-stage process.

[0095] In this second embodiment, the reaction of components (i)-(iii) may be catalyzed by a strong nucleophile such as benzyltriethylammonium chloride, tetraphenyl phosphonium bromide, or triphenylphosphine or by a Lewis acid, such as chromium (III) acetate, to form a polyester. The polyester is then reacted with component (iv) in the same reaction vessel by addition of component (iv) to the reaction mixture. The choice of monoacid and / or monoepoxide is determined by analysis of the end groups of the polyester and each equivalent of acid end-group is reacted with a stoichiometric amount of ethylenically unsaturated monoepoxide and each equivalent of hydroxyl or epoxide end group is reacted with a stoichiometric amount of ethylenically unsaturated monoacid. If analysis shows that less than 10 meq / g of a functional group is present, its presence may optionally be neglected when calculating the addition of component (iv).

[0096] The reaction generally involves heating components (i)-(iv) / (i)-(iii) at temperatures ranging between 100 and 200°C, under pressure or vacuum to remove water and other by-products. Catalysts may be used during the reaction.

[0097] One essential feature of the polyester compound of the present invention is that it is the reaction product of components (ii) and (iii), wherein the weight ratio of component (ii) to component (iii) is less than 30:1. Preferably, the weight ratio of component (ii) to component (iii) is between 30:1 and 4.1:1; more preferably, the weight ratio of component (ii) to component (iii) is between 25: 1 and 4.2:1; most preferably, the weight ratio of component (ii) to component (iii) is between 20: 1 and 4.3:1.

[0098] Another essential feature of the polyester compound of the invention is that the reaction mixture used to obtain the polyester compound comprises less than 3% of monoacid other than (meth)acrylic acid based on the total weight of the reactive species (i.e. the total weight of acids, alcohols and epoxides used to prepare the polyester compound). Preferably, the reaction mixture contains less than 2.5 wt.%, more preferably less than 2 wt.%, most preferably less than 1.8%, less than 1.5%, less than 1.2%, less than 1 wt.%, less than 0.9% or even less than 0.5 wt.%, of monoacid other than (meth)acrylic acid based on the total weight of the reactive species.

[0099] In a preferred embodiment, the reaction mixture used to obtain the polyester compound comprises less than 3 wt.%, preferably less than 2.5 wt.%, most preferably less than 1.8%, less than 1.5%, less than 1.2%, less than 1 wt.%, less than 0.9% or even less than 0.5 wt.%, of a monoacid having at least 10, preferably at least 12, more preferably at least 14, more preferably at least 16, and most preferably at least 18, carbon atoms, based on the total weight of the reactive species (i.e. the total weight of acids, alcohols and epoxides used to prepare the polyester compound). Said monoacid may be saturated or unsaturated, preferably unsaturated.

[0100] As explained above with respect to the composition of the present invention, the adjustment of the levels of monoacids and triacids in the polyester compound of the present invention introduce enough of a crosslink density in compositions comprising it to boost the cure speed, without impacting the solvent resistance of formulations incorporating it. Additionally, while faster cure speed is generally known to cause a decrease in the coating mechanical performances, such as impact resistance, the mechanical performance of the coatings incorporating the polyester compound of the present inventions are not adversely impacted.

[0101] One component used to obtain the polyester compound of the present invention is component (i), i.e., at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or polyepoxide.

[0102] The diol, polyol, diepoxide and poly epoxide used to prepare the polyester compound are not intended to be limited to specific structures only. The term “polyol” as used herein refers to any compound comprising at least two (two or more) hydroxyl groups, in its broadest meaning. The term “diol” as used herein refers to any compound comprising two hydroxyl groups, in its broadest meaning. The term “polyepoxide” as used herein refers to any compound comprising at least two (two or more) epoxy groups ( ° ), in its broadest meaning. The term “diepoxide” as used herein refers to any compound comprising two epoxy groups ( ° ), in its broadest meaning.

[0103] Component (i) comprises at least one diol, polyol, diepoxide or poly epoxide. Component (i) may comprise a mixture of compounds selected from a diol, a polyol, a diepoxide, and a poly epoxide.

[0104] In particular, component (i) may comprise or consist of at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol or diepoxide.

[0105] In particular, component (i) may comprise or consist of an acyclic diol or polyol, an aryl diol or polyol, an aryl polyepoxide or diepoxide, or a component comprising at least two glycidyl ether functions, for example, two, three or four glycidyl ether functions, or a mixture thereof.

[0106] In particular, component (i) may comprise or consist of a diprimary diol and / or component (ii) may comprise or consist of a diacid having its COOH groups in alpha position of methylene (-CH2-) groups. The primary diol may for example be 1,4-butanediol, ethylene glycol, 1,6-hexanediol, 1,8-octandiol or a mixture thereof.

[0107] In particular, component (i) may comprise or consist of a diol comprising or substituted with at least one ester group, at least one alkoxy late group or both. In some embodiments, component (i) comprises or consists of a diol comprising or substituted with one ester group.

[0108] In particular, component (i) may comprise or consist of an acyclic polyol, preferably an acyclic diol. In particular, component (i) may comprise or consist of a linear or branched aliphatic polyol or diol, preferably a linear or branched aliphatic diol. For example, component (i) may comprise or consist of a diol selected among alkyl diols (or alkyl glycols), alkoxy lated alkyl diols, polyether diols, neopentyl glycols, alkylated neopentyl glycols, and alkoxylated neopentyl glycols. More particularly, the acyclic diol may be selected from the group consisting of propanediols (e.g., 1.2-propoanediol or 1,3-propanediol), butanediols (e.g., 1,4-butanediol), pentanediols (e.g., 1,5-pentanediol), hexanediols (e.g., 1,6-hexanediol), octanediols, decanediols, dodecanediols, 2-methyl- 1.3 -propanediol, 2-methyl-2,4-pentanediol, and neopentyl glycol and mixtures thereof. The acyclic diol may be selected from the group consisting of ethoxylated alkyl diols, propoxylated alkyl diols, ethoxylated neopentyl glycol, propoxylated neopentyl glycol, and mixtures thereof. The acyclic diol may an alkylated neopentyl glycol, for example neopentyl monohydroxy pivalate (HPN glycol), also called neopentyl glycol mono(hydroxy pivalate). The acyclic diol may a poly ether diol, for example be selected from the group consisting of polyethylene oxide), polypropylene oxide), poly(butylene oxide) and mixtures thereof.

[0109] In particular, component (i) may comprise or consist of an aryl polyol or an aryl diol, preferably an aryl diol. More particularly, the aryl diol may be selected from the group consisting of hydroquinone (HQE), alkoxylated HQE (for example, ethoxylated HQE and propoxylated HQE), bisphenol-A (BP A), alkoxylated BPA (for example ethoxylated bisphenol A and propoxylated bisphenol A), propoxylated BPA, and bis-ethylene glycol terephthalate.

[0110] In particular, component (i) may comprise or consist of a first substituted or unsubstituted aliphatic, aryl, or heteroaryl diol and a second diol selected from the group consisting of tricyclodecanedimethanol, cyclohexane dimethanol, hydrogenated bisphenol A and hydrogenated bisphenol F, wherein the second diol is present in an amount of not more than 45 mol.% of the total diol content.

[0111] In particular, component (i) may comprise or consist of an aryl poly epoxide or an aryl diepoxide, preferably an aryl diepoxide. The aryl diepoxide may be selected from the group consisting of bisphenol A diglycidyl ether (BADGE), bisphenol F diglycidyl ether (BFDGE), bisphenol S diglycidyl ether (BPSGE), and mixtures thereof.

[0112] In particular, component (i) may comprise or consist of a diepoxide or poly epoxide or a component comprising at least two glycidyl ether functions. More particularly, the diepoxide may be selected from the group consisting of alkyl diol diglycidyl ether (e.g., 1,4-butanediol diglycidyl ether), aryl diol diglycidyl ether (e.g., hydrogenated bisphenol A diglycidyl ether), and polyether diol diglycidyl ether (e.g., dipropylene glycol diglycidyl ether). Additionally, the diepoxide may be the neopentyl glycol diglycidyl ether. The diepoxide, optionally polyepoxide, may be selected from 1,2,3,4-diepoxybutane; 1,2,4,5-diepoxypentane; 1,2,5,6-diepoxyhexane; 1,2,7,8-diepoxyoctane; 1,2, 9, 10-diepoxy decane; bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, brominated bisphenol A diglycidyl ether, brominated bisphenol F diglycidyl ether, brominated bisphenol S diglycidyl ether, epoxy novolak resin, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, hydrogenated bisphenol S diglycidyl ether, 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane-l,4-dioxane, bis(3,4-epoxycyclohexylmethyl)adipate, vinylcyclohexene oxide, 4-vinylepoxycyclohexane, bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate, 3,4-epoxy-6-methylcyclohexyl-3',4'-epoxy-6'-methylcyclohexanecarboxylate, methylenebis(3,4-epoxycyclohexane), dicyclopentadiene diepoxide, di(3,4-epoxycyclohexylmethyl) ether of ethylene glycol, ethylenebis(3, 4-epoxycyclohexanecarboxylate), ethylene glycol diglycidyl ether, 1,2- or 1,3-propylene glycol diglycidyl ether, 1,2-, 1,3- or 1,4-butanediol diglycidyl ether, 1,5 -pentanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,7-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1,9-nonanediol diglycidyl ether, 1,10-decanediol diglycidyl ether, 1,12-dodecanediol diglycidyl ether, 2 -methyl- 1,3 -propanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 2, 2-diethyl- 1,3 -propane diol diglycidyl ether, 3 -methyl- 1,5 -pentanediol diglycidyl ether, 3,3-dimethyl-l,5-pentanediol diglycidyl ether, 2, 4-diethy 1-1, 5 -pentanediol diglycidyl ether, 3,3-butylethyl-l,5-pentane diol diglycidyl ether, di-, tri- or tetra(ethylene glycol) diglycidyl ether, di-, tri- or tetra(l,2-propylene glycol) diglycidyl ether, di-, tri- or tetra(l,3-propylene glycol) diglycidyl ether, di-, tri- or tetra(l,4-butylene glycol) diglycidyl ether, a polyethylene glycol) diglycidyl ether, a polypropylene glycol) diglycidyl ether, a poly(trimethylene glycol) diglycidyl ether, a poly(tetramethylene glycol) diglycidyl ether, a polyethylene glycol-co-propylene glycol) diglycidyl ether, glycerol triglycidyl ether, a polyglycerol polyglycidyl ether, trimethylolmethane triglycidyl ether, trimethylolethane triglycidyl ether, trimethylolpropane triglycidyl ether, di(trimethylolpropane) tetraglycidyl ether, pentaerythritol tetraglycidyl ether, diglycidyl cyclohexanedicarboxylate, cyclohexane diglycidyl ether, cyclohexane- 1,4-dimethanol diglycidyl ether, tricyclodecane dimethanol diglycidyl ether, isosorbide diglycidyl ether, pyrocatechol diglycidyl ether, resorcinol diglycidyl ether, cardol diglycidyl ether, phloroglucinol triglycidyl ether, pyrogallol triglycidyl ether, tris(hydroxyphenyl)methane triglycidyl ether, tris(hydroxyphenyl)ethane triglycidyl ether, diglycidyl phthalate, diglycidyl terephthalate, diglycidyl isophthalate, polyglycidyl ethers of a polyether polyol obtained by the addition of one or morealkylene oxides to an aliphatic polyhydric alcohol such as ethylene glycol, propylene glycol, and glycerol, diglycidyl esters of aliphatic long-chain (C6-C22) dibasic acids, monoglycidyl ethers of aliphatic higher alcohols, monoglycidyl ethers of phenol, cresol, butyl phenol, or polyether alcohols obtained by the addition of alkylene oxide to these compounds, glycidyl esters of higher fatty acids, an epoxidized vegetable oil (such as epoxidized soybean oil and epoxidized linseed oil), epoxybutylstearic acid, epoxyoctylstearic acid, epoxidized polybutadiene, triglycidyl isocyanurate and the like.

[0113] In a preferred embodiment, component (i) comprises or consists of at least one compound selected from a diol, a polyol having at least 3 OH groups and mixtures thereof. In particular, component (i) may comprise or consist of at least one compound selected from a diol, a polyol having 3 to 6 OH groups and mixtures thereof. More particularly, component (i) may comprise or consist of at least one compound selected from a diol, a polyol having 3 or 4 OH groups, and mixtures thereof.

[0114] In a preferred embodiment, component (i) comprises or consists of at least one diol or a mixture of at least one diol and at least one polyol having at least 3, in particular 3 to 6, more particularly 3 or 4, OH groups.

[0115] When component (i) comprises at least one diol, it may correspond to the following formula (32) and when component (i) comprises at least one polyol having at least 3 OH groups, it may correspond to the following formula (33):wherein A, P and x are as defined above.

[0116] In a preferred embodiment, component (i) comprises or consists of at least one diol selected from:- a cyclic diol, in particular a cyclic diol selected from hydroquinone (HQE), hydroquinone bis(2-hydroxyethyl) ether (HQEE), bisphenol-A, B, F or S, bis-ethylene glycol terephthalate, pyrocatechol, resorcinol, cardol, cyclohexanediol, cyclohexane dimethanol, norbomene dimethanol, norbornane dimethanol, tricyclodecanediol, tricyclodecanedimethanol, dicyclopentadiene diol, hydrogenated bisphenol-A, B, F or S, a dianhydrohexitol (i.e. isosorbide, isomannide, isoidide), as well as the alkoxy lated (e.g. ethoxylated and / or propoxylated) derivatives thereof;- a diol comprising an ester bond, in particular neopentyl glycol mono(hydroxypivalate) having the following structure:and mixtures thereof.

[0117] In another preferred embodiment, component (i) comprises or consists of a mixture of at least one diol and at least one polyol having at least 3 OH groups, in particular 3 to 6 OH groups, more particularly 3 or 4 OH groups. The molar ratio of the at least one diol to the at least one polyol having at least 3 OH groups may be from 1 to 50, preferably from 2 to 25, more preferably from 5 to 20. In particular, the at least one diol may be selected from ethylene glycol, propanediols (e.g., 1,2-propanediol or 1,3 -propanediol), butanediols (e.g., 1,2-, 1,3- or 1,4-butanediol), pentanediols (e.g., 1.5-pentanediol), hexanediols (e.g., 1,6-hexanediol), octanediols, decanediols, dodecanediols, 2-methyl-l,3-propanediol, 2-methyl-2,4-pentanediol, neopentyl glycol, 2, 2-diethyl- 1,3 -propanediol, 3-methyl-l,5-pentanediol, 3,3-dimethyl-l,5-pentanediol, 2,4-diethyl-l,5-pentanediol, 3,3-butylethyl- 1.5-pentane diol, neopentyl glycol mono(hydroxy pivalate), di-, tri- or tetra(ethylene glycol), di-, trior tetra(l,2-propylene glycol), di-, tri- or tetra(l,3-propylene glycol), di-, tri- or tetra(l,4-butylene glycol), a polyethylene glycol), a polypropylene glycol), a poly(trimethylene glycol), a poly(tetramethylene glycol), a poly(ethylene glycol-co-propylene glycol, hydroquinone (HQE), hydroquinone bis(2-hydroxyethyl) ether (HQEE), bisphenol-A, B, F or S, bis-ethylene glycol terephthalate, pyrocatechol, resorcinol, cardol, cyclohexanediol, cyclohexane dimethanol, norbornene dimethanol, norbornane dimethanol, tricyclodecanediol, tricyclodecanedimethanol, dicyclopentadiene diol, hydrogenated bisphenol-A, B, F or S, a dianhydrohexitol (i.e. isosorbide, isomannide, isoidide), as well as the alkoxylated (e.g. ethoxylated and / or propoxylated) derivatives thereof and mixtures thereof. In particular, the at least one polyol having at least 3 OH groups may be selected from trimethylolmethane, trimethylolethane, trimethylolpropane, di(trimethylolpropane), triethylolpropane, pentaerythritol, di(pentaerythritol), tri(pentaerythritol), glycerol, di-, tri- or tetraglycerol, a polyglycerol, an alditol (i.e. erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galactitol, fucitol or iditol), tris(2-hydroxyethyl)isocyanurate, phloroglucinol, pyrogallol, tris(hydroxyphenyl)methane, tris(hydroxyphenyl)ethane, as well as the alkoxylated (e.g. ethoxylated and / or propoxylated) derivatives thereof and mixtures thereof.

[0118] One component used to obtain the polyester compound of the present invention is component (ii), i.e. at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid. Another component used to obtain the polyester compound of the present invention is component (iii), i.e. at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid. Preferably, both of said diacid and triacid have at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms. In some specific examples, the diacid has 36 carbon atoms and the triacid has 54 carbon atoms. Such diacid and triacid may be commercialized as a mixture. Reference can notably be made to UNIDYME™ 18 from KRATON, long chain (C36) acid mixture containing about 17% trimer acids and about 1.5% monomer acids.

[0119] In particular, components (ii) and / or (iii) may respectively comprise or consist of a substituted or unsubstituted phenyl or naphthyl diacid and / or triacid; preferably, both components (ii) and (iii) comprise or consist of a substituted or unsubstituted phenyl or naphthyl diacid and triacid.

[0120] In particular, components (ii) and / or (iii) may respectively comprise or consist of a substituted or unsubstituted norbomenyl diacid and / or triacid; preferably, both components (ii) and (iii) comprise or consist of a substituted or unsubstituted norbornenyl diacid and triacid.

[0121] In particular, components (ii) and / or (iii) may respectively comprise or consist of a substituted or unsubstituted non-hydrogenated diacid and / or triacid; preferably, both components (ii) and (iii) comprise or consist of substituted or unsubstituted non-hydrogenated diacid and triacid.

[0122] In a preferred embodiment, component (ii) comprises or consists of at least one diacid according to the following formula (34) and component (iii) comprises or consists of at least one triacid according to the following formula (35)wherein D and T are as defined above for formula (30), (31a) and (3 lb).

[0123] In a preferred embodiment, component (ii) may comprise or consist of at least one fatty acid dimer and component (iii) may comprise or consist of at least one fatty acid trimer.

[0124] Fatty acid dimers and trimers may be as defined previously.

[0125] The at least one fatty acid dimer can be a fatty acid dimer having 32 to 40, preferably 34 to 38, more preferably 36 carbon atoms. Such a compound can be obtained by dimerization of fatty acids having 16 to 20, preferably 17 to 19, more preferably 18 carbon atoms. The at least one fatty acid dimer can be an unsaturated fatty acid dimer, also known as a non-hydrogenated fatty acid dimer.

[0126] The at least one fatty acid trimer can be a fatty acid trimer having 48 to 60, preferably 51 to 57, more preferably 54 carbon atoms. Such a compound can be obtained by trimerization of fatty acids having 16 to 20, preferably 17 to 19, more preferably 18 carbon atoms. The at least one fatty acid trimer can be an unsaturated fatty acid trimer, also known as a non-hydrogenated fatty acid trimer.

[0127] One component used to obtain the polyester compound of the present invention is component (iv), i.e. at least one ethylenically unsaturated monoacid and / or at least one ethylenically unsaturated monoepoxide. Synthetic equivalent of monoacids, such as acyl halides and anhydrides are encompassed by the term monoacid.

[0128] In particular, component (iv) may comprise or consist of at least one ethylenically unsaturated monoacid selected from acrylic acid, methacrylic acid, an acryloyl halide (such asacryloyl chloride), a methacryloyl halide (such as methacryloyl chloride), acrylic anhydride, methacrylic anhydride or mixtures thereof; preferably acrylic acid, methacrylic acid, or mixtures thereof.

[0129] In particular, component (iv) may comprise or consist of at least one ethylenically unsaturated monoepoxide selected from glycidyl acrylate, glycidyl methacrylate, allyl glycidyl ether, acrylic acid glycidyl ether, methacrylic acid glycidyl ether or mixtures thereof.

[0130] In particular, component (iv) may comprise or consist of at least one the ethylenically unsaturated monoacid and / or monoepoxide at least one ethylenically unsaturated monoepoxide selected from (meth)acrylic acid, glycidyl (meth)acrylate, and the reaction products of hydroxy(alkyl) (meth)acrylates with phthalic or succinic anhydride or acid. Hydroxyalkyl (meth)acrylates include 4-hydroxybutyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate. The adducts with succinic and phthalic acid with 2-hydroxyethyl (meth)acrylate are commercially available as CN146 (HEA monophthalate), CN147 (HEA monosuccinate), and CN149 (HEMA monophthalate) from Sartomer.

[0131] The polyester compound of the present invention may be such that it has a number average molecular weight (Mn) of at least about 750 g / mol, preferably between about 1,000 and about 15,000 g / mol, between about 1,250 and about 10,000 g / mol, or between about 1,500 and about 7,000 g / mol.

[0132] The polyester compound of the present invention may be such that it has a weight average molecular weight (Mw) of at least about 1,000 g / mol, preferably between about 2,000 and about 30,000 g / mol, between about 3,000 and about 20,000 g / mol, or between about 3,500 and about 15,000 g / mol.

[0133] The polyester compound of the present invention may be such that it has a poly dispersity index (D) of less than about 3, preferably less than about 2.5 or more preferably less than about 2.

[0134] Number averaged (Mn), weight averaged (Mw), or Z-averaged (Mz) molecular weights may be measured using gel permeation chromatography (GPC) with polystyrene standards. Polydispersity index (D) may be calculated as Mw / Mn.Curable compositions

[0135] The curable composition of the invention may comprise at least the composition comprising compound I or II of the present invention, as described herein, or it may comprise at least the polyester compound of the present invention, as described herein,

[0136] The curable composition of the invention may comprise from 5 wt.% to 99.9 wt.% of one or more of such compositions / compounds, for example from 10 wt.% to 99.5 wt.%, from 20 wt.% to 99 wt.%, from 30 wt.% to 98 wt.%, from 50 wt.% to 97 wt.%, or from 60 wt.% to 95 wt.%, based on the total weight of the curable composition.

[0137] The curable composition may comprise several distinct compositions / compounds of the present invention, for example two or more. For example, the curable composition comprises a mixture of compositions / compounds of the present invention having distinct segments, for example prepared starting from distinct components.

[0138] The curable composition of the invention may further comprise one or more of the following:a. a polymerizable component comprising one or more ethylenically unsaturated compounds and / or one or more cationically polymerizable compounds distinct from the polyester compound of the invention;b. an inhibitor;c. an initiator selected from a free radical initiator, a cationic initiator, and mixtures thereof; d. an additive selected from the group consisting of antioxidants, ultraviolet absorbers, photostabilizers, foam inhibitors, flow or leveling agents, colorants, pigments, dispersants (wetting agents), slip additives, fillers, thixotropic agents, matting agents, waxes, any additive conventionally utilized in coating, sealant, adhesive, ink or molding compositions, and mixtures thereof.Polymerizable component

[0139] The curable composition of the invention may comprise a polymerizable component.

[0140] A polymerizable component comprises or consists of one or more ethylenically unsaturated compounds and / or one or more cationically polymerizable compounds.

[0141] The polymerizable component is distinct from the polyester compound of the invention.

[0142] The polymerizable component may comprise one or more ethylenically unsaturated compounds. In particular, the polymerizable component may comprise one or more ethylenically unsaturated compounds selected from a (meth)acrylate-functionalized monomer, a (meth)acrylate-functionalized oligomer and mixtures thereof. In particular, the polymerizable component may comprise one or more (meth)acrylate functionalized monomers.

[0143] As used herein, the term “(meth)acrylate-functionalized monomer” means a monomer comprising a (meth)acrylate group, in particular an acrylate group. The term “(meth)acry late-functionalized oligomer” means an oligomer comprising a (meth)acrylate group, in particular an acrylate group.

[0144] The polymerizable component may comprise at least one (meth)acrylate-functionalized monomer. The polymerizable component may comprise a mixture of (meth)acrylate-functionalized monomers.

[0145] A (meth)acrylate-functionalized monomer may have a molecular weight of less than 600 g / mol, in particular from 100 to 550 g / mol, more particularly 200 to 500 g / mol.

[0146] A (meth)acry late-functionalized monomer may have 1 to 6 (meth)acrylate groups, in particular 1 to 3 (meth)acrylate groups.

[0147] The polymerizable component may comprise a mixture of (meth)acry late-functionalized monomers having different functionalities. For example, the polymerizable component may comprise a mixture of a (meth)acrylate-functionalized monomer containing a single acrylate or methacrylate group per molecule (referred to herein as “mono(meth)acrylate-functionalized monomer”) and a (meth)acrylate-functionalized monomer containing 2 or more, preferably 2 or 3, acrylate and / or methacrylate groups per molecule (referred to herein as “poly(meth)acrylate-functionalized monomer”).

[0148] In particular, the polymerizable component may comprise at least one mono(meth)acrylate-functionalized monomer.

[0149] Examples of suitable mono(meth)acrylate-functionalized monomers include, but are not limited to, mono-(meth)acrylate esters of aliphatic alcohols (wherein the aliphatic alcohol may be straight chain, branched or alicyclic and may be a mono-alcohol, a di-alcohol or a polyalcohol, provided only one hydroxyl group is esterified with (meth)acrylic acid); mono-(meth)acrylate esters of aromatic alcohols (such as phenols, including alkylated phenols); mono-(meth)acrylate esters of alkylaryl alcohols (such as benzyl alcohol); mono-(meth)acrylate esters of oligomeric and polymeric glycols such as diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, polyethylene glycol, and polypropylene glycol); mono-(meth)acrylate esters of monoalkyl ethers of glycols and oligoglycols; mono-(meth)acrylate esters of alkoxylated (e.g., ethoxylated and / or propoxylated) aliphatic alcohols (wherein the aliphatic alcohol may be straight chain, branched or alicyclic and may be a mono-alcohol, a di-alcohol or a polyalcohol, provided only one hydroxyl group of the alkoxylated aliphatic alcohol is esterified with (meth)acrylic acid); mono-(meth)acrylate esters of alkoxylated (e.g., ethoxylated and / or propoxylated) aromatic alcohols (such as alkoxylated phenols); (poly)caprolactone mono(meth)acrylates; and the like.

[0150] A (poly)caprolactone mono(meth)acrylate may be obtained by ring-opening polymerization of e-caprolactone initiated with a hydroxyalkyl (meth)acrylate. A preferred (meth)caprolactone (meth)acrylate is (poly)caprolactone 2-hydroxyethyl (meth)acrylate according to the following formula:CH2=CR5-C(=O)-O-CH2-CH2-[O-(C=O)-(CH2)5]t-OHwherein R5 is H or methyl and t ranges from 1 to 20, preferably from 2 to 10.

[0151] The following compounds are specific examples of mono(meth)acry late-functionalized monomers suitable for use in the polymerizable component: methyl (meth)acrylate; ethyl (meth)acrylate; n-propyl (meth)acrylate; n-butyl (meth) aery late; isobutyl (meth)acrylate; n-hexyl (meth)acrylate; 2-ethylhexyl (meth)acrylate; n-octyl (meth)acrylate; isooctyl (meth)acrylate; n-decyl(meth)acrylate; n-dodecyl (meth)acrylate; tridecyl (meth)acrylate; tetradecyl (meth)acrylate; hexadecyl (meth)acrylate; 2-hydroxyethyl (meth)acrylate; 2- and 3-hydroxypropyl (meth)acrylate; 2-methoxyethyl (meth)acrylate; 2-ethoxyethyl (meth)acrylate; 2- and 3 -ethoxy propyl (meth)acrylate; tetrahydrofurfuryl (meth)acrylate; 2-(2-ethoxyethoxy)ethyl (meth)acrylate; cyclohexyl (meth)acrylate; glycidyl (meth)acrylate; isodecyl (meth)acrylate; lauryl (meth)acrylate; 2-phenoxyethyl (meth)acrylate; alkoxylated phenol (meth)acrylates; alkoxylated nonylphenol (meth)acrylates; cyclic trimethylolpropane formal (meth)acrylate; isobornyl (meth)acrylate; tricyclodecanemethanol (meth)acrylate; tert-butylcyclohexanol (meth)acrylate; trimethylcyclohexanol (meth)acrylate; diethylene glycol monomethyl ether (meth)acrylate; diethylene glycol monoethyl ether (meth)acrylate; diethylene glycol monobutyl ether (meth)acrylate; triethylene glycol monoethyl ether (meth)acrylate; ethoxylated lauryl (meth)acrylate; methoxy polyethylene glycol (meth)acrylates; 3 -(2 -hydroxy alky l)oxazolidinone (meth)acrylates; a (poly)caprolactone mono(meth)acrylate; as well as the alkoxylated (i.e. ethoxylated and or propoxylated) derivatives thereof and combinations thereof.

[0152] The polymerizable component may comprise at least one poly(meth)acry late-functionalized monomer.

[0153] A poly(meth)acrylate-functionalized monomer may have from 2 to 6 (meth)acrylate groups, in particular from 2 to 6 acrylate groups.

[0154] Examples of suitable poly(meth)acry late -functionalized monomers include acrylate and methacrylate esters of polyols. Examples of suitable polyols are ethylene glycol, propanediols (e.g., 1,2-propanediol or 1,3-propanediol), butanediols (e.g., 1,2-, 1,3- or 1,4-butanediol), pentanediols (e.g., 1,5-pentanediol), hexanediols (e.g., 1,6-hexanediol), octanediols, decanediols, dodecanediols, 2-methyl-l,3-propanediol, 2-methyl-2,4-pentanediol, neopentyl glycol, 2, 2-diethy 1-1, 3 -propanediol, 3-methyl-l,5-pentanediol, 3,3-dimethyl-l,5-pentanediol, 2,4-diethyl-l,5-pentanediol, 3,3-butylethyl-l,5-pentane diol, neopentyl glycol mono(hydroxypivalate), di-, tri- or tetra(ethylene glycol), di-, tri- or tetra(l,2-propylene glycol), di-, tri- or tetra(l,3-propylene glycol), di-, tri- or tetra(l,4-butylene glycol), a polyethylene glycol), a polypropylene glycol), a poly (trimethylene glycol), a poly(tetramethylene glycol), a polyethylene glycol-co-propylene glycol, hydroquinone (HQE), hydroquinone bis(2 -hydroxyethyl) ether (HQEE), bisphenol-A, B, F or S, bis-ethylene glycol terephthalate, pyrocatechol, resorcinol, cardol, cyclohexanediol, cyclohexane dimethanol, norbornene dimethanol, norbornane dimethanol, tricyclodecanediol, tricyclodecanedimethanol, dicyclopentadiene diol, hydrogenated bisphenol-A, B, F or S, a dianhydrohexitol (i.e. isosorbide, isomannide, isoidide), trimethylolmethane, trimethylolethane, trimethylolpropane, di(trimethylolpropane), triethylolpropane, pentaerythritol, di(pentaerythritol), tri(pentaerythritol), glycerol, di-, tri- or tetraglycerol, a polyglycerol, an alditol (i.e. erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galactitol, fucitol or iditol), tris(2-hydroxyethyl)isocyanurate,phloroglucinol, pyrogallol, tris(hydroxyphenyl)methane, tris(hydroxyphenyl)ethane, as well as the alkoxylated (e.g. ethoxylated and / or propoxylated) derivatives thereof. Such polyols may be fully or partially esterified (with (meth)acrylic acid, (meth)acrylic anhydride, (meth)acryloyl chloride or the like), provided they contain at least two (meth)acrylate functional groups per molecule.

[0155] The following compounds are specific examples of poly(meth)acrylate-functionalized monomers suitable for use in the polymerizable component: bisphenol A di(meth)acrylate; hydrogenated bisphenol A di(meth)acrylate; ethylene glycol di(meth)acrylate; diethylene glycol di(meth)acrylate; triethylene glycol di(meth)acrylate; tetraethylene glycol di(meth)acrylate; polyethylene glycol di(meth)acrylate; propylene glycol di(meth)acrylate; dipropylene glycol di(meth)acrylate; tripropylene glycol di(meth)acrylate; tetrapropylene glycol di(meth)acrylate; polypropylene glycol di(meth)acrylate; polytetramethylene glycol di(meth)acrylate; 1,2-butanediol di(meth)acrylate; 2,3-butanediol di(meth)acrylate; 1,3-butanediol di(meth)acrylate; 1,4-butanediol di(meth)acrylate; 1,5 -pentanediol di(meth)acrylate; 1,6-hexanediol di(meth)acrylate; 1,8-octanediol di(meth)acrylate; 1,9-nonanediol di(meth)acrylate; 1,10-nonanediol di(meth)acrylate; 1,12-dodecanediol di(meth)acrylate; neopentyl glycol di(meth)acrylate; 2-methyl-2,4-pentanediol di(meth)acrylate; polybutadiene di(meth)acrylate; cyclohexane-l,4-dimethanol di(meth)acrylate; tricyclodecane dimethanol di(meth)acrylate; metallic di(meth)acrylates; modified metallic di(meth)acrylates; glyceryl di(meth)acrylate; glyceryl tri(meth)acrylate; trimethylolethane tri(meth)acrylate; trimethylolethane di(meth)acrylate; trimethylolpropane tri (meth)acry late; trimethylolpropane di(meth)acrylate; pentaerythritol di(meth)acrylate; pentaerythritol tri(meth)acrylate; pentaerythritol tetra(meth)acrylate, di(trimethylolpropane) diacrylate; di(trimethylolpropane) triacrylate; di(trimethylolpropane) tetraacrylate, sorbitol penta(meth)acrylate; di(pentaerythritol) tetraacrylate; di(pentaerythritol) pentaacrylate; di(pentaerythritol) hexa(meth)acrylate; tris(2-hydroxyethyl) isocyanurate tri (meth)acry late; as well as the alkoxylated (e.g., ethoxylated and / or propoxylated) derivatives thereof; and combinations thereof.

[0156] The polymerizable component may comprise a (meth)acrylate-functionalized oligomer. The polymerizable component may comprise a mixture of (meth)acry late-functionalized oligomers.

[0157] A (meth) acrylate functionalized oligomer may have 1 to 18 (meth)acrylate groups, in particular 2 to 6 (meth)acrylate groups, more particularly 2 to 6 acrylate groups.

[0158] A (meth)acrylate functionalized oligomer may have a number average molecular weight equal or more than 600 g / mol, in particular 800 to 15,000 g / mol, more particularly 1,000 to 5,000 g / mol.

[0159] In particular, the polymerizable component may comprise a (meth)acry late-functionalized oligomer selected from the group consisting of epoxy (meth)acrylates, polyester (meth)acrylates,polyether (meth)acrylates, urethane (meth)acrylates, (meth)acrylated poly(meth)acrylates and mixtures thereof.

[0160] The polymerizable component may comprise one or more cationically -polymerizable compound.

[0161] The term “cationically-polymerizable compound” means a compound comprising a polymerizing functional group which polymerizes via a cationic mechanism, for example a heterocyclic group or a carbon-carbon double bond substituted with an electrodonating group. In a cationic polymerization mechanism, a cationic initiator forms a Bronsted or Lewis acid species that binds to the cationically-polymerizable compound which then becomes reactive and leads to chain growth by reaction with another cationically-polymerizable compound.Inhibitor

[0162] The curable composition of the invention may comprise the composition or the compound of the present invention, as well as at least one inhibitor. According to these embodiments, the composition may comprise from 10 ppm to 5 wt.% of one or more inhibitors, for example from 20 ppm to 4 wt.%, from 50 ppm to 3 wt.%, from 100 ppm to 1 wt.%, or from 120 ppm to 0.1 wt.%, based on the total weight of the curable composition.

[0163] Inhibitors may be introduced in the curable composition in order to provide adequate storage stability and shelf life. As described above, an inhibitor may typically retard or prevent reaction or curing of polymerizable functional groups present in a composition, notably in the absence of radiation.

[0164] As described above, any of the inhibitors known in the art related to ethylenically unsaturated compounds may be utilized in the composition of the invention.Initiator

[0165] The curable composition may comprise an initiator selected from a free radical initiator, a cationic initiator and mixtures thereof. The curable composition may comprise a mixture of a free radical initiator and a cationic initiator.

[0166] Initiators are generally divided into two classes, depending on their mode of action: free radical initiators and cationic initiators.

[0167] Free radical initiators encompass both photoinitiators and thermal initiators.

[0168] Photoinitiators are compounds that that can generate free radicals upon exposure to light of an appropriate wavelength and / or intensity. Photoinitiators can adopt two different modes of action, and are classified by mode of action as Norrish Type I and Norrish Type II photoinitiators. As used herein, the term “activity” with reference to Norrish Type I and Norrish Type II activity is intended to relate to Norrish photoinitiation and analogous reactions. For instance, a photoinitiatorhaving Norrish Type I activity within the scope of this invention would be a photoinitiator characterized by a cleavage reaction into two radical fragments of the original photoinitiator on exposure to light. For an initiator having Norrish Type II activity, exposure to light causes the abstraction of an atom, such as hydrogen, to generate the radical.

[0169] Thermal initiators are compounds that can generate free radicals upon exposure to heat and / or in the presence of a reducing agent.

[0170] Cationic initiators are often salts, for instance iodonium and sulfonium salts. When these salts are activated (i.e., by irradiation with actinic radiation such as light), they undergo homolytic bond cleavage forming radicals that react with a proton donor to give a Bronsted or Lewis acid. The generated acid then initiates the polymerization.

[0171] The curable composition may comprise a free radical initiator which is a photoinitiator, in particular a photoinitiator having Norrish type I activity and / or Norrish type II activity, more particularly a free radical initiator having Norrish type I activity.

[0172] Classes of suitable free radical photoinitiators suitable for use in the curable compositions as described herein include, but are not limited to, benzoins, benzoin ethers, acetophenones, a-hydroxy acetophenones, benzyl ketals, anthraquinones, phosphine oxides, acylphosphine oxides, a-hydroxyketones, phenylglyoxylates, a-aminoketones, benzophenones, thioxanthones, xanthones, acridine derivatives, phenazene derivatives, quinoxaline derivatives, triazines, benzoyl formates, aromatic oximes, metallocenes, acylsilyl or acylgermanyl compounds, camphorquinones, polymeric derivatives thereof, and mixtures thereof.

[0173] Examples of suitable free radical photoinitiators include, but are not limited to, 2-methylanthraquinone, 2 -ethylanthraquinone, 2 -chloroanthraquinone, 2-benzyanthraquinone, 2-tert-butylanthraquinone, l,2-benzo-9,10-anthraquinone, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, alpha-methylbenzoin, alpha-phenylbenzoin, Michler's ketone, 2,2-dialkoxybenzophenones, 1-hydroxyphenyl ketones, benzophenone, 4,4'-bis-(diethylamino) benzophenone, acetophenone, 2,2-diethyloxyacetophenone, diethyloxyacetophenone, 2-isopropylthioxanthone, thioxanthone, diethyl thioxanthone, 1,5 -acetonaphthylene, benzil ketone, a-hydroxy keto, 2,4,6-trimethylbenzoyldiphenyl phosphine oxide, benzyl dimethyl ketal, 2,2-dimethoxy-l,2-diphenylethanone, 1-hydroxycylclohexyl phenyl ketone, 2-methyl-l-[4-(methylthio) phenyl]-2-morpholinopropanone-l, 2-hydroxy-2-methyl-l-phenyl-propanone, oligomeric a-hydroxy ketones, benzoyl phosphine oxides, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, ethyl(2,4,6-trimethylbenzoyl)phenyl phosphinate, anisoin, anthraquinone, anthraquinone-2-sulfonic acid, (benzene) tricarbonylchromium, benzil, benzoin isobutyl ether, benzophenone / 1-hydroxy cyclohexyl phenyl ketone (50 / 50 blend), 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 4-benzoylbiphenyl, 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(dimethylamino)benzophenone, camphor quinone, 2-chlorothioxanthen-9-one, dibenzosuberenone, 4,4'-dihydroxybenzophenone, 2,2-dimethoxy-2-phenylacetophenone, 4-(dimethylamino)benzophenone, 4,4'-dimethylbenzil, 2,5-dimethylbenzophenone, 3,4-dimethylbenzophenone, diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide / 2-hydroxy-2-methylpropiophenone, 50 / 50 blend, 4'-ethoxyacetophenone, 2,4,6-trimethylbenzoyldiphenylphophine oxide, phenyl bis(2,4,6-trimethyl benzoyl)phosphine oxide, ferrocene, 3'-hydroxyacetophenone, 4'-hydroxyacetophenone, 3 -hydroxy benzophenone, 4-hydroxybenzophenone, 1 -hydroxy cyclohexyl phenyl ketone, 2-hydroxy-2-methylpropiophenone, 2-methylbenzophenone, 3 -methylbenzophenone, methybenzoylformate, 2-methyl-4'-(methylthio)-2-morpholinopropiophenone, phenanthrenequinone, 4'-phenoxyacetophenone, (cumene)cyclopentadienyl iron(ii) hexafluorophosphate, 9,10-diethoxy and 9,10-dibutoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, thioxanthen-9-one and combinations thereof.

[0174] Preferred free radical photoinitiators include a benzophenone (such as those available from Sartomer under the trademarks Speedcure™ BP, Speedcure™ 7005, and Speedcure™ 7006), a thioxanthone (such as available from Sartomer under the trademarks Speedcure™ 7010 and Speedcure™ ITX), an a-hydroxy acetophenone, an acylphosphine oxide (such as available from Sartomer under the trademarks Speedcure™ BPO, Speedcure™ TPO and Speedcure™ TPO-L) and combinations thereof.Additives (e.g., fillers, elastomers)

[0175] The curable compositions of the present invention may optionally contain one or more additives selected from the group consisting of antioxidants, ultraviolet absorbers, photostabilizers, foam inhibitors, flow or leveling agents, colorants, pigments, dispersants (wetting agents), slip additives, fillers, elastomers, thixotropic agents, matting agents, waxes, any additive conventionally utilized in coating, sealant, adhesive, ink or molding compositions, and mixtures thereof.

[0176] In some embodiments, the curable compositions of the invention comprise one or more fillers. Examples of fillers include glass particles, quartz, graphite powder, carbon black and aluminum oxide powder.

[0177] In some embodiments, the curable compositions of the invention comprise one or more elastomers. Examples of elastomers include RTV rubber and silicone rubber.

[0178] In some embodiments, the curable compositions of the invention are solvent-free. In such embodiments, they notably contain no organic solvent.End-use applications

[0179] The composition and the polyester compound of the present invention may be used in various formulations, for example formulations for adhesives, inks, or coatings. In particular, thecomposition and the polyester compound of the present invention are particularly well-suited for battery coatings.

[0180] The composition and the polyester compound of the present invention may also be used as a constituent of a solvent-resistant encapsulant formulation, such as a coating for batteries.

[0181] The present invention is also directed to a method of making a formulation for an adhesive, an ink or a coating, in particular a coating for battery, comprising adding the composition or the polyester compound of the present invention as one of the components of such formulation.

[0182] The compositions of the invention are especially useful as curable compositions, or UV curable resins, that is, compositions intended for use as adhesives, coatings and inks.Method of making a cured composition

[0183] The present invention also relates to a method of making a cured composition of the invention, which comprises curing the composition as described herein, or curing formulations comprising the polyester compound described herein.

[0184] The cured compositions obtained herein exhibit mechanical properties particularly well-suited for battery coatings. These properties enable the coatings to withstand the harsh operating conditions of batteries, such as exposure to electrolytes, elevated temperatures, and repeated chargedischarge cycles, while maintaining adhesion, flexibility, and chemical resistance.

[0185] Curing may be accelerated or facilitated by supplying energy to the composition, such as by exposing the composition to a radiation source, such as visible or UV light, infrared radiation, and / or electron beam radiation and / or by heating the composition. The cured composition is the reaction product obtained from curing compositions described herein or formulations comprising the polyester compound described herein.

[0186] In some embodiments, the method of making a cured composition comprises exposing the composition to ultraviolet light (UV) radiation, electron beam (EB) radiation and / or heat.

[0187] The compositions of the present invention, and formulations comprising the polyester compound described herein, are particularly well suited to being cured using LED (Light Emitting Diode) curing, e.g., UV LED curing, using radiation from a UV LED device.

[0188] In particular, the compositions and formulations comprising the polyester compound of the invention are well-suited for use in applications requiring a fast curing.

[0189] The compositions and formulations of the invention may be applied to a substrate surface, then cured by exposure to a source of curing (for example a dose of radiation).ASPECTS OF THE INVENTION

[0190] The present invention may be according to any one of the following aspects.Aspect 1. A composition comprising at least one compound I of structure I:wherein:each R1is independently H or C1-C6 alkyl, preferably H or methyl;each R2is independently a residue of at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or polyepoxide;R3comprises residues of at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid and at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid, both of said diacid and triacid having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms;each R4is independently the residue of at least one ethylenically unsaturated monoacid and / or of at least one ethylenically unsaturated monoepoxide, preferably -C(=O)-;n is from 1 to 25, preferably from 1 to 10; andthe weight ratio of diacid to triacid in R3is less than 30:1, preferably the weight ratio of diacid to triacid in R3is between 30:1 and 4.1:1, more preferably between 25:1 and 4.2:1, most preferably between 20:1 and 4.3:1;wherein the composition contains less than 3 wt.%, preferably less than 2.5 wt.%, more preferably less than 2 wt.%, of a residue of a monoacid other than (meth)acrylic acid, based on the total weight of the composition.Aspect 2. The composition of aspect 1, wherein the compound has the structure II:wherein:each R1is independently H or C1-C6 alkyl, preferably H or methyl;each R2is independently a residue of at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or polyepoxide;R3comprises residues of at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid and at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid, both of said diacid and triacid having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms;n is from 1 to 25, preferably from 1 to 10; andthe weight ratio of diacid to triacid in R3is less than 30:1, preferably the weight ratio of diacid to triacid in R3is between 30:1 and 4.1:1, more preferably between 25:1 and 4.2:1, most preferably between 20:1 and 4.3:1;wherein the composition contains less than 3 wt.%, preferably less than 2.5 wt.%, more preferably less than 2 wt.%, of a residue of a monoacid other than a residue of (meth)acrylic acid, based on the total weight of the composition.Aspect 3. The composition of aspect 1 or 2, wherein the composition contains less than 1.8%, less than 1.5%, less than 1.2%, less than 1 wt.%, less than 0.9% or even less than 0.5 wt.%, of a residue of a monoacid other than a residue of (meth)acrylic acid based on the total weight of the composition.Aspect 4. The composition of any one of aspects 1-3, wherein the composition of the present invention contains less than 1.8%, less than 1.5%, less than 1.2%, less than 1 wt.%, less than 0.9% or even less than 0.5 wt.%, of a residue of a monoacid having at least 10, preferably at least 12, more preferably at least 14, more preferably at least 16, and most preferably at least 18, carbon atoms, based on the total weight of the composition.Aspect 5. The composition of any one of aspects 1 -4, wherein each R2is independently a residue of an acyclic diol or polyol, an aryl diol or polyol, an aryl polyepoxide or diepoxide, or a component comprising at least two glycidyl ether functions (for example, two, three or four glycidyl ether functions).Aspect 6. The composition of any one of aspects 1-4, wherein R2comprises or is substituted with at least one ester group, at least one alkoxylate group or both, preferably R2comprises or is substituted with one ester group.Aspect 7. The composition of any one of aspects 1-4, wherein R2is the residue of an acyclic polyol, preferably an acyclic diol, more preferably a linear or branched aliphatic polyol or diol, most preferably a linear or branched aliphatic diol.Aspect 8. The composition of aspect 7, wherein the acyclic diol is selected from the group consisting of propanediols (preferably 1,2-propoanediol or 1,3 -propanediol), butanediols (preferably 1,4-butanediol), pentanediols (preferably 1,5-pentanediol), hexanediols (preferably 1,6-hexanediol), octanediols, decanediols, dodecanediols, 2-methyl-l,3-propanediol, 2-methyl-2,4-pentanediol, and neopentyl glycol; or is a polyether diol, preferably selected from the group consisting of polyethylene oxide), polypropylene oxide), poly(butylene oxide);Aspect 9. The composition of any one of aspects 1-6, wherein R2is the residue of an alkylated neopentyl glycol, preferably neopentyl monohydroxy pivalate (HPN glycol).Aspect 10. The composition of any one of aspects 1-6, wherein R2is the residue of an aryl polyol or an aryl diol, preferably an aryl diol; more preferably selected from the group consisting of hydroquinone (HQE), alkoxylated HQE (for example, ethoxylated HQE and propoxylated HQE), bisphenol-A (BP A), alkoxylated BPA (for example ethoxylated bisphenol A and propoxylated bisphenol A), propoxylated BPA, and bis-ethylene glycol terephthalate.Aspect 11. The composition of any one of aspects 1-6, wherein R2comprises a first residue of a first substituted or unsubstituted aliphatic, aryl, or heteroaryl diol and a second residue of a second diol selected from the group consisting of tricyclodecanedimethanol, cyclohexane dimethanol, hydrogenated bisphenol A and hydrogenated bisphenol F, wherein the second diol is present in an amount of not more than 45 mol.% of the total diol content.Aspect 12. The composition of any one of aspects 1-4, wherein R2is the residue of an aryl polyepoxide or diepoxide, preferably selected from the group consisting of bisphenol A diglycidyl ether (BADGE), bisphenol F diglycidyl ether (BFDGE), and bisphenol S diglycidyl ether (BPSGE). Aspect 13. The composition of any one of aspects 1-4, wherein R2is the residue of a diepoxide or polyepoxide or a component comprising at least two glycidyl ether functions; preferably a diepoxide selected from the group consisting of alkyl diol diglycidyl ether (e.g., 1,4-butanediol diglycidyl ether), aryl diol diglycidyl ether (e.g., hydrogenated bisphenol A diglycidyl ether), and polyether diol diglycidyl ether (e.g., dipropylene glycol diglycidyl ether) or preferably a neopentyl glycol diglycidyl ether.Aspect 14. The composition of any one of aspects 1-4, wherein each R2is independently selected from the residue of a diol or a polyol having at least 3 OH groups; in particular, each R2is independently selected from the residue of a diol or a polyol having 3 to 6 OH groups; more particularly, each R2is independently selected from the residue of a diol or a polyol having 3 or 4 OH groups.Aspect 15. The composition of any one of aspects 1-4, wherein each R2is independently selected from the residue of a diol or part of the R2groups are independently selected from the residue of a diol and the remaining part of the R2groups are selected from the residue of a polyol having at least 3, in particular 3 to 6, more particularly 3 or 4, OH groups.Aspect 16. The composition of aspect 15, wherein the residue of a diol corresponds to the following formula (1) and the residue of a polyol having at least 3 OH groups corresponds to the following formula (2a) or (2b):whereinR1and R4are as defined in aspect 1;each A is independently an aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl- each R5, R’S, Re, R’e, Rs, R’s, Ris and R’15 is independently H or methyl;- each W is independently -O- or -S-;- each Cy is independently an optionally substituted ring or polycyclic ring system, in particular an optionally substituted cyclopentylene, cyclohexylene, phenylene, naphthylene, bicyclooctylene or tricyclodecylene;- each Lois independently a bond or a linker such as Aik, -C(=O)-, -C(=O)-O-Alk-O- C(=O)-, -SO-, -SO2-, -C(=CCl2)- and -Alk-Ph-Alk-;- Aik is an optionally substituted alkylene;- Ph is an optionally substituted phenylene;- each e, j, m, n, o and r is independently an integer from 2 to 20;- each s is independently an integer from 0 to 20;- each s’ is independently an integer from 1 to 20;- each f, h and u is independently an integer from 2 to 4;- t is an integer equal to 0 or 1;- each g, 1, p and q is independently an integer from 1 to 20;- each v is independently an integer from 0 to 10, in particular from 1 to 6; - each i is independently an integer from 0 to 20 with the proviso that at least one i is not 0;- k is an integer from 3 to 12.Aspect 18. The composition of aspect 16 or 17, wherein P is selected from:- a trivalent moiety according to any one of formulae (15) to (20):wherein:- each R15and R16is independently a linear or branched alkylene;- each Ru and R’n is independently H or methyl;- each Ris and R’is is independently H, alkyl or alkoxy, preferably each RI8and R’is is alkyl;- each R19 is independently a linear or branched alkylene;- Rf is H or methyl;- w is an integer equal to 0 or 1;- each a’ is independently an integer from 0 to 2 with the proviso that not more than one a’ is equal to 0, preferably each a’ is equal to 1 or one a’ is equal to 0 and the two other a’ are equal to 1;- each a’ ’ is independently an integer from 0 to 2 with the proviso that not more than one a” is equal to 0, preferably each a” is equal to 1 or one a” is equal to 0 and the two other a” are equal to 1;- each b’ is independently an integer from 2 to 4, in particular 2;- each c’ is independently an integer from 0 to 10, in particular from 1 to 6;a tetravalent moiety according to any one of formulae (21) to (24):wherein:- each R20, R’20, R22 and R’22 is independently H or methyl;- each R21 and R25 is independently a linear or branched alkylene;- each R23 and R24 is independently H, alkyl or alkoxy, preferably alkyl;- each d’ is independently an integer from 0 to 2 with the proviso that not more than one d’ is equal to 0, preferably each d’ is equal to 1;- each d’ ’ is independently an integer from 0 to 2 with the proviso that not more than one d” is equal to 0, preferably each d” is equal to 1;- each e’ and g’ is independently an integer from 2 to 4, in particular 2;- each f ’ and h’ is independently an integer from 0 to 10, in particular from 1 to 6; - a tetra-, penta- or hexavalent moiety according to formula (25):wherein:5 - each R26and R’2e is independently H or methyl;- each i’ is independently an integer from 2 to 4, in particular 2;- each j ’ is independently an integer from 0 to 10, in particular from 1 to 6;- k’ is an integer from 1 to 3;- a tri-, tetra-, penta- or hexavalent moiety according to formula (26):wherein- each Rgis independently selected from H, alkyl, cycloalkyl, aryl, alkaryl, aralkyl, alkoxy, -C(=O)O-Alkyl and a halogen atom;- k” is an integer from 1 to 4;5 - a hexavalent moiety according to any one of formulae (27) to (29):wherein- each R27, R’27, R29 and R’29 is independently H or methyl;- each R28 is independently a linear or branched alkylene;- each 1’ and n’ is independently an integer from 2 to 4, in particular 2;- each m’ and o’ is independently an integer from 0 to 10, in particular from 1 to 6. Aspect 19. The composition of any one of aspects 1-4 and 14-18, wherein each R2is independently selected from:- the residue of a cyclic diol, in particular the residue of a cyclic diol selected from hydroquinone (HQE), hydroquinone bis(2-hydroxyethyl) ether (HQEE), bisphenol-A, B, F or S, bis-ethylene glycol terephthalate, pyrocatechol, resorcinol, cardol, cyclohexanediol, cyclohexane dimethanol, norbomene dimethanol, norbomane dimethanol, tricyclodecanediol, tricyclodecanedimethanol, dicyclopentadiene diol, hydrogenated bisphenol-A, B, F or S, a dianhydrohexitol (i.e. isosorbide, isomannide, isoidide), as well as the alkoxylated (e.g. ethoxylated and / or propoxylated) derivatives thereof and mixtures thereof; or- the residue of a diol comprising an ester bond, in particular the residue of neopentyl glycol mono(hydroxypivalate) having the following structure:Aspect 20. The composition of any one of aspects 1-4 and 14-18, wherein part of the R2groups are independently selected from the residue of a diol and the remaining part of the R2groups areindependently selected from the residue of a polyol having at least 3 OH groups, in particular 3 to 6 OH groups, more particularly 3 or 4 OH groups.Aspect 21. The composition of aspect 20, wherein the molar ratio of residues derived from the diol to residues derived from the polyol having at least 3 OH groups is from 1 to 50, preferably from 2 to 25, more preferably from 5 to 20.*Aspect 22. The composition of aspect 20 or 21, wherein part of the R2groups are independently selected from the residue of a diol selected from ethylene glycol, propanediols (e.g., 1,2-propanediol or 1,3-propanediol), butanediols (e.g., 1,2-, 1,3- or 1,4-butanediol), pentanediols (e.g., 1,5-pentanediol), hexanediols (e.g., 1,6-hexanediol), octanediols, decanediols, dodecanediols, 2-methyl-1,3 -propanediol, 2-methyl-2,4-pentanediol, neopentyl glycol, 2, 2-diethy 1-1, 3 -propanediol, 3 -methyl -1,5 -pentanediol, 3,3-dimethyl-l,5-pentanediol, 2,4-diethyl-l,5-pentanediol, 3,3-butylethyl-l,5-pentane diol, neopentyl glycol mono(hydroxypivalate), di-, tri- or tetra(ethylene glycol), di-, tri- or tetra(l,2-propylene glycol), di-, tri- or tetra(l,3-propylene glycol), di-, tri- or tetra(l,4-butylene glycol), a polyethylene glycol), a polypropylene glycol), a poly(trimethylene glycol), a poly(tetramethylene glycol), a poly(ethylene glycol-co-propylene glycol, hydroquinone (HQE), hydroquinone bis(2-hydroxyethyl) ether (HQEE), bisphenol-A, B, F or S, bis-ethylene glycol terephthalate, pyrocatechol, resorcinol, cardol, cyclohexanediol, cyclohexane dimethanol, norbornene dimethanol, norbornane dimethanol, tricyclodecanediol, tricyclodecanedimethanol, dicyclopentadiene diol, hydrogenated bisphenol-A, B, F or S, a dianhydrohexitol (i.e. isosorbide, isomannide, isoidide), as well as the alkoxylated (e.g. ethoxylated and / or propoxylated) derivatives thereof and mixtures thereof.Aspect 23. The composition of any one of aspects 20-22, wherein the remaining part of the R2groups are independently selected from the residue of a polyol having at least 3 OH groups selected from trimethylolmethane, trimethylolethane, trimethylolpropane, di(trimethylolpropane), triethylolpropane, pentaerythritol, di(pentaerythritol), tri(pentaerythritol), glycerol, di-, tri- or tetraglycerol, a polyglycerol, an alditol (i.e. erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galactitol, fucitol or iditol), tris(2-hydroxyethyl)isocyanurate, phloroglucinol, pyrogallol, tris(hydroxyphenyl)methane, tris(hydroxyphenyl)ethane, as well as the alkoxylated (e.g. ethoxylated and / or propoxylated) derivatives thereof and mixtures thereof.Aspect 24. The composition of any one of aspects 1-23, wherein R3comprises residues of a substituted or unsubstituted phenyl or naphthyl diacid and / or triacid, preferably of both substituted or unsubstituted phenyl or naphthyl diacid and triacid; more preferably, wherein both of the diacid and triacid have at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms.Aspect 25. The composition of any one of aspects 1-23, wherein R3comprises residues of a substituted or unsubstituted norbomenyl diacid and / or triacid, preferably of both substituted or unsubstituted norbornenyl diacid and triacid; more preferably, wherein both of the diacid and triacid have at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms.Aspect 26. The composition of any one of aspects 1-23, wherein R3comprises residues of a substituted or unsubstituted non-hydrogenated diacid and / or triacid, preferably of both substituted or unsubstituted non-hydrogenated diacid and triacid; more preferably, wherein both of the diacid and triacid have at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms.Aspect 27. The composition of any one of aspects 1-23, wherein R3comprises a residue of a fatty acid dimer and a residue of a fatty acid trimer; in particular, R3comprises a residue of a non-hydrogenated fatty acid dimer and a residue of a non-hydrogenated fatty acid trimer.Aspect 28. The composition of any one of aspects 1-23, wherein part of the R3groups are independently according to the following formula (30) and the remaining part of the R3groups are independently according to the following formula (31a) or (31b):whereinR1, R2and R4are as defined in any one of aspects 1-23;D is a substituted or unsubstituted aliphatic, aryl, or heteroaryl divalent moiety having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms;T is a substituted or unsubstituted aliphatic, aryl, or heteroaryl trivalent moiety having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms.Aspect 29. The composition of aspect 28, wherein D corresponds to the residue obtained by removing the COOH groups of a fatty acid dimer.Aspect 30. The composition of aspect 28 or 29, wherein T corresponds to the residue obtained by removing the COOH groups of a fatty acid trimer.Aspect 31. The composition of aspect 29 or 30, wherein the fatty acid dimer is a fatty acid dimer having 32 to 40, preferably 34 to 38, more preferably 36 carbon atoms.Aspect 32. The composition of any one of aspects 29-31, wherein the fatty acid trimer is a fatty acid trimer having 48 to 60, preferably 51 to 57, more preferably 54 carbon atoms.Aspect 33. The composition of any one of aspects 1-32, comprising at least 51 mol.% of compound I or II where R1is H, preferably at least 60 mol.%, at least 70 mol.%, at least 80 mol.% or at least 85 mol.%, based on the total number of moles of compound I or II in the composition. Aspect 34. The composition of any one of aspects 1-33, wherein compound I or II has a number average molecular weight (Mn) of at least about 750 g / mol, preferably between about 1,000 and about 15,000 g / mol, between about 1,250 and about 10,000 g / mol, or between about 1,500 and about 7,000 g / mol.Aspect 35. A polyester compound which is the reaction product of:(i) at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or polyepoxide;(ii) at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid;(iii) at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid; and(iv) at least one ethylenically unsaturated monoacid and / or at least one ethylenically unsaturated monoepoxide;wherein the weight ratio of component (ii) to component (iii) is less than 30:1, preferably between 30:1 and 4.1:1, more preferably between 25:1 and 4.2:1, most preferably between 20:1 and 4.3:1; andthe reaction mixture used to obtain the polyester compound comprises less than 3% preferably less than 2.5 wt.%, more preferably less than 2 wt.%, of monoacid other than (meth)acrylic acid based on the total weight of the reactive species.Aspect 36. The compound of aspect 35, wherein the reaction mixture contains less than 1.8%, less than 1.5%, less than 1.2%, less than 1 wt.%, less than 0.9% or even less than 0.5 wt.%, of monoacid other than (meth)acrylic acid based on the total weight of the reactive species.Aspect 37. The compound of aspect 35, wherein the reaction mixture contains less than 1.8%, less than 1.5%, less than 1.2%, less than 1 wt.%, less than 0.9% or even less than 0.5 wt.%, of monoacid having at least 10, preferably at least 12, more preferably at least 14, more preferably at least 16, and most preferably at least 18, carbon atoms, based on the total weight of the reactive species.Aspect 38. The compound according to any one of aspects 35-37, wherein component (iv) comprises or consists of at least one ethylenically unsaturated monoacid.Aspect 39. The compound of any one of aspects 35-38, wherein component (i) comprises or consists of a diprimary diol and component (ii) comprises or consists of diacid having its COOH groups in alpha position of methylene (-CH2-) groups.Aspect 40. The compound of any one of aspects 35-39, wherein component (i) comprises or consists of a diol comprising or substituted with at least one ester group, at least one alkoxy late group or both.Aspect 41. The compound of any one of aspects 35-40, wherein component (i) comprises or consists of an acyclic polyol, preferably an acyclic diol, more preferably a linear or branched aliphatic polyol or diol, most preferably a linear or branched aliphatic diol acyclic diol, preferably a linear or branched aliphatic diol.Aspect 42. The compound of aspect 41, wherein the acyclic diol is selected from the group consisting of propanediols (preferably 1,2-propoanediol or 1,3 -propanediol), butanediols (preferably 1,4-butanediol), pentanediols (preferably 1,5-pentanediol), hexanediols (preferably 1,6-hexanediol), octanediols, decanediols, dodecanediols, 2-methyl-l,3-propanediol, 2-methyl-2,4-pentanediol, and neopentyl glycol; and mixtures thereof.Aspect 43. The compound of any one of aspects 35-40, wherein component (i) comprises or consists of an alkylated neopentyl glycol, preferably neopentyl monohydroxy pivalate (HPN glycol). Aspect 44. The compound of any one of aspects 35-40, wherein component (i) comprises or consists of an aryl polyol or an aryl diol, preferably an aryl diol; more preferably selected from the group consisting of hydroquinone (HQE), alkoxylated HQE (for example, ethoxylated HQE and propoxylated HQE), bisphenol-A (BP A), alkoxylated BPA (for example ethoxylated bisphenol A and propoxylated bisphenol A), propoxylated BPA, and bis-ethylene glycol terephthalate.Aspect 45. The compound of any one of aspects 35-40, wherein component (i) comprises or consists of a first substituted or unsubstituted aliphatic, aryl, or heteroaryl diol and a second diol selected from the group consisting of tricyclodecanedimethanol, cyclohexane dimethanol, hydrogenated bisphenol A and hydrogenated bisphenol F, wherein the second diol is present in an amount of not more than 45 mol.% of the total diol content.Aspect 46. The compound of any one of aspects 35-38, wherein component (i) comprises or consists of an aryl poly epoxide or an aryl diepoxide, preferably an aryl diepoxide; more preferably an aryl diepoxide selected from the group consisting of bisphenol A diglycidyl ether (BADGE), bisphenol F diglycidyl ether (BFDGE), and bisphenol S diglycidyl ether (BPSGE).Aspect 47. The compound of any one of aspects 35-38, wherein component (i) comprises or consists of a diepoxide or polyepoxide or a component comprising at least two glycidyl ether functions; preferably a diepoxide selected from the group consisting of alkyl diol diglycidyl ether (e.g., 1,4-butanediol diglycidyl ether), aryl diol diglycidyl ether (e.g., hydrogenated bisphenol A diglycidyl ether), and polyether diol diglycidyl ether (e.g., dipropylene glycol diglycidyl ether) or preferably a neopentyl glycol diglycidyl ether.Aspect 48. The compound of any one of aspects 35-38, wherein component (i) comprises or consists of at least one compound selected from a diol, a polyol having at least three OH groups and mixtures thereof; in particular, component (i) comprises or consists of at least one compound selected from a diol, a polyol having 3 to 6 OH groups and mixtures thereof; more particularly, component (i) comprises or consists of at least one compound selected from a diol, a polyol having 3 or 4 OH groups, and mixtures thereof.Aspect 49. The compound of any one of aspects 35-38 and 48, wherein component (i) comprises or consists of at least one diol or a mixture of at least one diol and at least one polyol having at least 3, in particular 3 to 6, more particularly 3 or 4, OH groups.Aspect 50. The compound of aspect 48 or 49, wherein the at least one diol corresponds to the following formula (32) and the at least one polyol having at least 3 OH groups correspond to the following formula (33):wherein A, P and x are as defined in any one of aspects 16-18.Aspect 51. The compound of any one of aspects 35-38 and 48-50, wherein component (i) comprises or consists of at least one diol selected from:- a cyclic diol, in particular a cyclic diol selected from hydroquinone (HQE), hydroquinone bis(2-hydroxyethyl) ether (HQEE), bisphenol-A, B, F or S, bis-ethylene glycol terephthalate, pyrocatechol, resorcinol, cardol, cyclohexanediol, cyclohexane dimethanol, norbomene dimethanol, norbornane dimethanol, tricyclodecanediol, tricyclodecanedimethanol, dicyclopentadiene diol, hydrogenated bisphenol-A, B, F or S, a dianhydrohexitol (i.e. isosorbide, isomannide, isoidide), as well as the alkoxylated (e.g. ethoxylated and / or propoxy lated) derivatives thereof;- a diol comprising an ester bond, in particular neopentyl glycol mono(hydroxypivalate) having the following structure:CH3o CH3HOCH2-C — C-OCH2-C-CH2OHCH3CH3and mixtures thereof.Aspect 52. The compound of any one of aspects 35-38 and 48-50, wherein component (i) comprises or consists of a mixture of at least one diol and at least one polyol having at least 3 OH groups, in particular 3 to 6 OH groups, more particularly 3 or 4 OH groups.Aspect 53. The compound of aspect 52, wherein the molar ratio of the at least one diol to the at least one polyol having at least 3 OH groups may be from 1 to 50, preferably from 2 to 25, more preferably from 5 to 20.Aspect 54. The compound of aspect 52 or 53, wherein the at least one diol is selected from ethylene glycol, propanediols (e.g., 1,2-propanediol or 1,3-propanediol), butanediols (e.g., 1,2-, 1,3-or 1,4-butanediol), pentanediols (e.g., 1,5-pentanediol), hexanediols (e.g., 1,6-hexanediol), octanediols, decanediols, dodecanediols, 2-methyl- 1,3 -propanediol, 2-methyl-2,4-pentanediol, neopentyl glycol, 2,2-diethyl-l,3-propanediol, 3 -methyl- 1,5 -pentanediol, 3, 3 -dimethyl- 1,5-pentanediol, 2,4-diethyl-l,5-pentanediol, 3,3-butylethyl-l,5-pentane diol, neopentyl glycol mono(hydroxypivalate), di-, tri- or tetra(ethylene glycol), di-, tri- ortetra(l,2-propylene glycol), di-, tri- or tetra( 1,3 -propylene glycol), di-, tri- or tetra(l,4-butylene glycol), a polyethylene glycol), a polypropylene glycol), a poly (trimethylene glycol), a poly (tetramethylene glycol), a polyethylene glycol-co-propylene glycol, hydroquinone (HQE), hydroquinone bis(2 -hydroxyethyl) ether (HQEE), bisphenol-A, B, F or S, bis-ethylene glycol terephthalate, pyrocatechol, resorcinol, cardol, cyclohexanediol, cyclohexane dimethanol, norbomene dimethanol, norbomane dimethanol, tricyclodecanediol, tricyclodecanedimethanol, dicyclopentadiene diol, hydrogenated bisphenol-A, B, F or S, a dianhydrohexitol (i.e. isosorbide, isomannide, isoidide), as well as the alkoxylated (e.g. ethoxylated and / or propoxylated) derivatives thereof and mixtures thereof.Aspect 55. The compound of any one of aspects 52-54, wherein the at least one polyol having at least three OH groups is selected from trimethylolmethane, trimethylolethane, trimethylolpropane, di(trimethylolpropane), triethylolpropane, pentaerythritol, dipentaerythritol), tripentaerythritol), glycerol, di-, tri- or tetraglycerol, a poly glycerol, an alditol (i.e. erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galactitol, fucitol or iditol), tris(2-hydroxyethyl)isocyanurate, phloroglucinol, pyrogallol, tris(hydroxyphenyl)methane, tris(hydroxyphenyl)ethane, as well as the alkoxylated (e.g. ethoxylated and / or propoxylated) derivatives thereof and mixtures thereof Aspect 56. The compound of any one of aspects 35-55, wherein component (ii) and / or (iii) respectively comprise or consist of a substituted or unsubstituted phenyl or naphthyl diacid and / or triacid, preferably both components (ii) and (iii) comprise or consist of a substituted or unsubstitutedphenyl or naphthyl diacid and triacid; preferably wherein both of the diacid and triacid have at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms.Aspect 57. The compound of any one of aspects 35-56, wherein component (ii) and / or (iii) respectively comprise or consist of a substituted or unsubstituted norbornenyl diacid and / or triacid, preferably both components (ii) and (iii) comprise or consist of a substituted or unsubstituted norbornenyl diacid and triacid, preferably wherein both of the diacid and triacid have at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms.Aspect 58. The compound of any one of aspects 35-57, wherein component (ii) and / or (iii) respectively comprise or consist of a substituted or unsubstituted non-hydrogenated diacid and / or triacid, preferably both components (ii) and (iii) comprise or consist of a substituted or unsubstituted non-hydrogenated diacid and triacid, preferably wherein both of the diacid and triacid have at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms.Aspect 59. The compound of any one of aspects 35-58, wherein component (ii) comprises or consists of at least one diacid according to the following formula (34) and component (iii) comprises or consists of at least one triacid according to the following formula (35):wherein D and T are as defined in aspect 28.Aspect 60. The compound of any one of aspects 35-59, wherein component (ii) comprises or consists of at least one fatty acid dimer and component (iii) comprises or consists of at least one fatty acid trimer.Aspect 61. The compound of aspect 60, wherein the at least one fatty acid dimer is a fatty acid dimer having 32 to 40, preferably 34 to 38, more preferably 36 carbon atoms.Aspect 62. The composition of aspect 60 or 61, wherein the at least one fatty acid trimer is a fatty acid trimer having 48 to 60, preferably 51 to 57, more preferably 54 carbon atoms.Aspect 63. The compound of any one of aspects 35-62, wherein component (iv) comprises or consists of an ethylenically unsaturated monoacid selected from acrylic acid, methacrylic acid, an acryloyl halide (such as acryloyl chloride), a methacryloyl halide (such as methacryloyl chloride), acrylic anhydride, methacrylic anhydride or mixtures thereof; preferably acrylic acid, methacrylic acid, or mixtures thereof.Aspect 64. The compound of any one of aspects 35-62, wherein component (iv) comprises or consists of an ethylenically unsaturated monoepoxide selected from glycidyl acrylate, glycidyl methacrylate, allyl glycidyl ether, acrylic acid glycidyl ether, methacrylic acid glycidyl ether or mixtures thereof.Aspect 65. The compound of any one of aspects 35-64, having a number average molecular weight (Mn) of at least about 750 g / mol, preferably between about 1,000 and about 15,000 g / mol, between about 1,250 and about 10,000 g / mol, or between about 1,500 and about 7,000 g / mol. Aspect 66. The compound of any one of aspects 35-65, having a weight average molecular weight (Mw) of at least about 1,000 g / mol, preferably between about 2,000 and about 30,000 g / mol, between about 3,000 and about 20,000 g / mol, or between about 3,500 and about 15,000 g / mol.Aspect 67. The compound of any one of aspects 35-66, having a polydispersity index (D) of less than 3, preferably less than 2.5 or more preferably less than 2.Aspect 68. Use of the composition of any one of aspects 1-34 or the compound of any one of aspects 35-67, in a formulation for an adhesive, a coating or an ink.Aspect 69. Use of the composition of any one of aspects 1-34 or the compound of any one of aspects 35-67, as a constituent of a solvent-resistant encapsulant formulation, such as a coating for batteries.Aspect 70. A curable composition, comprising the composition of any one of aspects 1-34 or the compound of any one of aspects 35-67.Aspect 71. The curable composition of aspect 70, further comprising at least one or more of the following:a. a polymerizable component comprising one or more ethylenically unsaturated compounds and / or one or more cationically polymerizable compounds distinct from the composition of any of aspects 1-34 or the polyester compound of any one of aspects 35-67;b. an inhibitor;c. an initiator selected from a free radical initiator, a cationic initiator, and mixtures thereof; and / or d. an additive selected from the group consisting of antioxidants, ultraviolet absorbers, photostabilizers, foam inhibitors, flow or leveling agents, colorants, pigments, dispersants (wetting agents), slip additives, fdlers, thixotropic agents, matting agents, waxes, any additive conventionally utilized in coating, sealant, adhesive, ink or molding compositions, and mixtures thereof.

[0191] Although the foregoing invention has been described in some detail by way of illustration and example for purposes of clarity of understanding, one of skill in the art will appreciate that certain changes and modifications may be practiced within the scope of the appended claims. In addition,each reference provided herein is incorporated by reference in its entirety to the same extent as if each reference was individually incorporated by reference. Where a conflict exists between the instant application and a reference provided herein, the instant application shall dominate.EXAMPLES

[0192] The following examples illustrate the invention without limiting it.

[0193] Raw materialsTable 1

[0194] Methods used to measure the properties of the polyester compounds

[0195] The viscosity was measured using a Brookfield instrument at a temperature of 60°C using a #27 spindle and a rotational speed of 20 rpm.

[0196] Number averaged (Mn), weight averaged (Mw), or Z-averaged (Mz) molecular weights were measured using gel permeation chromatography (GPC) with polystyrene standards. Polydispersity index (D) was calculated as Mw / Mn.

[0197] Example 1 - Preparation of the inventive polyester compound

[0198] 90 g toluene, 33.22 g AA, 4.41 gMA, 296.24 gUNIDYME™ 18, 0.6 gBHT, 0.6 gMeHQ, 12.5 g 70% aqueous MsOH, 0.6 g 50% aqueous HP A, and 150.84 g TCD-DM were combined in a 500 mL round bottom flask equipped with a mechanical stirrer, gas sparge line, thermocouple, and reflux condenser. The reaction mixture was sparged with dry air while heating to reflux (beginning after ~25 minutes at 104°C and reaching a maximum temperature of 123°C reached after ~2 hours). The reaction was held at reflux until the inflection point in a potentiometric acid titration associated with carboxylic acids fell to < ~2.0 mg KOH / g (approximately 3 hr.). The reaction mixture was then cooled to ambient temperature and 34.4 g MAGNESOL®, 51.2 g toluene, and 1.5 g water were added and held at 100°C until no inflection point associated with MsOH was observed in potentiometric acid titration. After the equivalence point associated with MsOH was no longer present in the acid titration, the solution was filtered through a plug of diatomaceous earth with mass equal to 2 wt.% of the reaction mixture followed by 2.5, 8, and 25 pm filter papers under 118.6 kPa to 135.4 kPa (2.5-5 psig) external pressure. After filtration, solvent was removed under reduced pressure with air sparge (50 mmHg, 45-90°C) to give the final product as a viscous yellow oil.

[0199] Final product properties:Viscosity: 2,894 cP @ 60 °CMn= 3,455 g / molMw= 9,979 g / molMz= 52,663 g / molD = 2.89

[0200] Example 2 - Preparation of the formulation

[0201] Fillers / additives including TiO2, AEROSIL® R805, talc and the polyester compound were introduced into a Flacktek® polypropylene high-speed mixer cup, and the mixture was blended for 2 minutes at 2,000 rpm. Subsequently, the blended mixture was milled using 3-roll mills until a uniform dispersion of all additives in the oligomer was achieved. Following the milling process, the mixture underwent quality assessment for dispersion using a Hegman grind gauge (0-25pm). No discernible particles were observed on the gauge, indicating superior dispersion quality. Finally,monomers and photoinitiators were incorporated into the milled mixture, and the mixture was further blending for 2 minutes at 2,000 rpm using a high-speed mixer.

[0202] Two curable compositions a) and b) are exemplified herein, both consisting of 80 wt.% resin and 20 wt.% of fillers / additives.

[0203] Composition a)

[0204] Composition 1,1 (invention): the resin component consisted of 44 wt.% of SR833S, 27.33 wt.% of polyester compound, 6.67 wt.% of SR9051, 1 wt.% of SpeedCure BPO and 1 wt.% of SpeedCure73; the fdler / additive component consisted of 17 wt.% of talc, 2 wt.% of TiCL and 1 wt.% of AEROSIL® R805.

[0205] Composition 1,2 (comparative): the resin component consisted of 44 wt.% of SR833S, 27.33 wt.% of oligomer CN294, 6.67 wt.% of SR9051, 1 wt.% of SpeedCure BPO and 1 wt.% of SpeedCure73; the fdler / additive component consisted of 17 wt.% of talc, 2 wt.% of TiO2 and 1 wt.% of AEROSIL® R805.

[0206] Composition b)

[0207] In the compositions exemplified in this example, 2,1 (inventive) and 2,2 (comparative), the resin component consisted of 48 wt.% of the polyester compound of the invention, 12 wt.% of SR306F, 10 wt.% of SR833S, 5 wt.% of SR506, 3 wt.% of SR9054, 1 wt.% of SpeedCure BPO and 1 wt.% of Speedcure 73, and the fdler / additive component consisted of 17 wt.% of talc, 2 wt.% of TiO2 and 1 wt.% of Aerosil R805.

[0208] Curing method

[0209] Aluminum substrates were first wiped with toluene, followed by an acetone wipe. Coatings were then applied with a thickness of 60 pm on the aluminum substrate using a drawdown bar.

[0210] For formulations a), the coatings were cured using a LED light (395 nm) and fusion lamp (H bulb). For formulations b, the coatings were cured using Fusion (H bulb) 500 mJ / cm2- 17 fpm.

[0211] Environmental and Chemical Resistance Testing

[0212] Coated specimens underwent aging in both an environmental chamber at 85°C / 85%RH and through electrolyte soaking at 25°C for a duration of up to 4 weeks. The coated specimens that had been immersed in electrolyte solvents were dried with cleanroom wipes and alcohol before testing.

[0213] The electrolyte consisted of DEC, DMC, and EC in a 1:1:1 ratio.

[0214] For the electrolyte and salt screening test (E+S), LiCIO i salt was added to the above electrolyte in the following proportion: 13 wt.% LiClO4+ 29 wt.% EC + 29 wt.% DEC + 29 wt.% DMC.

[0215] The surfaces of the coated films were covered with an electrolyte -salt mixture and then subjected to an 85°C oven for 2 hours. Subsequently, they were rinsed with DI water and left at 60°C for 24 hours before measuring their properties.

[0216] Viscosity

[0217] Viscosity was measured in millipascal-seconds (mPa.s) at room temperature using a Brookfield RST CPS rheometer, with a torque setting of 50 M[%] and 60 (seconds) measurement points,

[0218] Volume resistivity (VR)

[0219] Volume resistivity was measured to determine the electrical insulating properties of the coating, more precisely how the coating material resists the flow of electrical current through its entire volume. The thickness of the cured samples was first measured using a Heidenhain Metro length gauge unit with an accuracy of ±0.2 pm and a measuring range of 0 to 12 mm. Film thickness measurements were taken at five different points within a 1.0 cm2area of the coated samples on the aluminum substrate, and their average was used to calculate volume resistivity. Volume resistivity was then measured in ohm-meters (Q m) using a Keithley 6517B electrometer with an 8009 resistivity test fixture at room temperature, following the ASTM D-257 standard. An alternating polarity of 500 V was applied to the cured film for 60 seconds before measurement.

[0220] Breakdown strength (BDS)

[0221] The breakdown strength of cured films was measured to assess their ability to withstand electrical stress and evaluate the coating's effectiveness as an electrical insulator in high-voltage applications. Breakdown strength of cured films was measured in volts per micrometers (V / pm) using the ASTM D-149 standard, ramping at 500 V / s. A 6.35 mm stainless steel ball on a brass substrate in 25°C silicone oil was utilized to minimize the electric field non-uniformity and the chances of a film defect being present at the test location. The cured film thickness was measured and recorded in each breakdown location prior to breakdown. Twenty measurements were taken for each film and the dataset was fitted using a 2-parameter Weibull distribution with a 95% confidence interval.

[0222] Adhesion (Adh.)

[0223] The adhesion of the coated resins to the aluminum plate was evaluated according to ASTM Standard D3359 using crosshatch test. In this test, a blade was used to cut small squares to the surface of the coatings, cutting passes make six cuts in the coating, second passes at 90° makes a square lattice pattern. A transparent tape was applied over the patterned surface and was pulled off quickly to release the amount of coating lifted off by the test tape. The crosshatch was rated on a 0 to 5 scale (with 5 being the highest adhesion strength) provided in the ASTM standard.

[0224] Pencil hardness (PH)

[0225] Graphite pencils with varied hardness were moved across a coating surface to test the hardness of the coating via ASTM D3363-05. The softest pencil creating a scratch on the surface of the coating determined its hardness in relation to graphite pencils.5

[0226] H stands for “hard”, such as H, 2H, 3H. 4H and 5H (the higher the number, the harder the pencil). HB is medium hardness, balanced. F stands for “fine”, with medium hardness.

[0227] Flexibility (Flex.)

[0228] Flexibility of the coatings was assessed using a conical mandrel test instrument in accordance with ASTM D522. The bend tester consisted of a bending lever with a roller that pivots 10 on a steel conical mandrel, allowing bends at 90° and 180° with diameters ranging from 4 mm to 34 mm. The lever was used to bend the coated substrate over the conical cone, and each sample was then inspected for cracks or crazing. A smaller diameter number indicates better flexibility; for example, a 4 mm diameter reflects superior flexibility compared to a 34 mm diameter, as it demonstrates the coating can withstand tighter bending without cracking.15

[0229] Impact Resistance

[0230] Impact resistance was assessed using a TQC SP1880 Impact Tester according to ASTM D2794. Aluminum panels, with the coating side down, were positioned under the beveled die. A one- kilogram weight was dropped from a predetermined height (10 to 50 cm with a 10 cm interval) onto the beveled die, and the coatings were then inspected for visible crazing and cracking. A successful 20 test exhibited no significant visible defects after impact.

[0231] Results

[0232] Table 2 below presents the results obtained with inventive composition 1.1. Table 3 below presents the results obtained with comparative composition 1.2.Table 2Table 3

[0233] The comparative composition 1.2 failed to meet the flexibility criteria and exhibited issues with adhesion (Adh.) and hardness (PH) after undergoing electrolyte testing. In contrast, the inventive composition 1.1 demonstrated strong adhesion, hardness, and flexibility.5

[0234] Tables 4-5 below present the results obtained with compositions 2.1 and 2.2.Table 4Table 5

[0235] The inventive compositions 2.1 showed better performance compared to comparative composition 2.2.

[0236] With cracking occurring at larger bend diameters, the composition of the present invention 2.1 generally shows better flexibility compared to the comparative composition 2.2. In particular, the results in Tables 4 and 5 indicate that the composition of the present invention 2.1 can endure a wider range of bending diameters, both at 90° and 180°, before and after the electrolyte and salt (E+S) screening test, compared to the comparative composition 2.2 which exhibited cracking within a narrower range. The inventive compositions demonstrate enhanced flexibility in comparison to the comparative composition.

[0237] The results in Table 5 also indicate better impact resistance for the composition of the present invention 2.1, with cracking occurring at a higher drop height compared to the comparative composition 2.2, which exhibited cracking at 10 cm.

Claims

CLAIMS1. A composition comprising at least one compound of structure I:wherein:each R1is independently H or C1-C6 alkyl, preferably H or methyl;each R2is independently a residue of at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or polyepoxide;R3comprises residues of at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid and at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid, both of said diacid and triacid having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms;each R4is independently the residue of at least one ethylenically unsaturated monoacid and / or of at least one ethylenically unsaturated monoepoxide, preferably -C(=O)-;n is from 1 to 25, preferably from 1 to 10; andthe weight ratio of diacid to triacid in R3is less than 30:1, preferably the weight ratio of diacid to triacid in R3is between 30:1 and 4.1:1, more preferably between 25:1 and 4.2:1, most preferably between 20:1 and 4.3:1;wherein the composition contains less than 3 wt.%, preferably less than 2.5 wt.%, more preferably less than 2 wt.%, of a residue of a monoacid other than a residue of (meth)acrylic acid, based on the total weight of the composition.

2. The composition of claim 1, wherein the compound has the structure II:wherein:each R1is independently H or C1-C6 alkyl, preferably H or methyl;each R2is independently a residue of at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or polyepoxide;R3comprises residues of at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid and at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid, both of said diacid and triacid having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms;n is from 1 to 25, preferably from 1 to 10; andthe weight ratio of diacid to triacid in R3is less than 30:1, preferably the weight ratio of diacid to triacid in R3is between 30:1 and 4.1:1, more preferably between 25:1 and 4.2:1, most preferably between 20: 1 and 4.3:1;wherein the composition contains less than 3 wt.%, preferably less than 2.5 wt.%, more preferably less than 2 wt.%, of a residue of a monoacid other than a residue of (meth)acrylic acid, based on the total weight of the composition.

3. The composition of claim 1 or 2, wherein the composition contains less than 1.8%, less than 1.5%, less than 1.2%, less than 1 wt.%, less than 0.9% or even less than 0.5 wt.%, of a residue of a monoacid other than a residue of (meth)acrylic acid based on the total weight of the composition.

4. The composition of any one of claims 1-3, wherein each R2is independently selected from the residue of a diol or part of the R2groups are independently selected from the residue of a diol and the remaining part of the R2groups are selected from the residue of a polyol having at least 3, in particular 3 to 6, more particularly 3 or 4, OH groups.

5. The composition of any one of claims 1-4, wherein each R2is independently selected from: - the residue of a cyclic diol, in particular the residue of a cyclic diol selected from hydroquinone (HQE), hydroquinone bis(2-hydroxyethyl) ether (HQEE), bisphenol-A, B, F or S, bis-ethylene glycol terephthalate, pyrocatechol, resorcinol, cardol, cyclohexanediol, cyclohexane dimethanol, norbomene dimethanol, norbomane dimethanol, tricyclodecanediol, tricyclodecanedimethanol, dicyclopentadiene diol, hydrogenated bisphenol-A, B, F or S, a dianhydrohexitol (i.e. isosorbide, isomannide, isoidide), as well as the alkoxylated (e.g. ethoxylated and / or propoxylated) derivatives thereof and mixtures thereof; or- the residue of a diol comprising an ester bond, in particular the residue of neopentyl glycol mono(hydroxypivalate) having the following structure:CH3O CH3HOCH2-C — C-OCH2-C-CH2OHCH3CH36. The composition of any one of claims 1-4, wherein part of the R2groups are independently selected from the residue of a diol and the remaining part of the R2groups are independently selected from the residue of a polyol having at least 3 OH groups, in particular 3 to 6 OH groups, more particularly 3 or 4 OH groups.

7. The composition of claim 6, wherein the molar ratio of residues derived from the diol to residues derived from the polyol having at least 3 OH groups is from 1 to 50, preferably from 2 to 25, more preferably from 5 to 20.*8. The composition of claim 6 or 7, wherein part of the R2groups are independently selected from the residue of a diol selected from ethylene glycol, propanediols, butanediols, pentanediols, hexanediols, octanediols, decanediols, dodecanediols, 2-methyl-1,3-propanediol, 2-methyl-2,4-pentanediol, neopentyl glycol, 2,2-diethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 3,3-dimethyl-1,5-pentanediol, 2,4-diethyl-1,5-pentanediol, 3,3-butylethyl-1,5-pentane diol, neopentyl glycol mono(hydroxypivalate), di-, tri- or tetra(ethylene glycol), di-, tri- or tetra(l,2-propylene glycol), di-, tri- or tetra( 1,3 -propylene glycol), di-, tri- or tetra(l,4-butylene glycol), a polyethylene glycol), a polypropylene glycol), a poly (trimethylene glycol), a poly (tetramethylene glycol), a polyethylene glycol-co-propylene glycol, hydroquinone, hydroquinone bis(2-hydroxyethyl) ether, bisphenol-A, B, F or S, bis-ethylene glycol terephthalate, pyrocatechol, resorcinol, cardol, cyclohexanediol, cyclohexane dimethanol, norbornene dimethanol, norbornane dimethanol, tricyclodecanediol, tricyclodecanedimethanol, dicyclopentadiene diol, hydrogenated bisphenol-A, B, F or S, a dianhydrohexitol, as well as the alkoxylated derivatives thereof and mixtures thereof.

9. The composition of any one of claims 6-8, wherein the remaining part of the R2groups are independently selected from the residue of a polyol having at least 3 OH groups selected from trimethylolmethane, trimethylolethane, trimethylolpropane, di(trimethylolpropane), triethylolpropane, pentaerythritol, di(pentaerythritol), tri(pentaerythritol), glycerol, di-, tri- or tetraglycerol, a polyglycerol, an alditol, tris(2-hydroxyethyl)isocyanurate, phloroglucinol, pyrogallol, tris(hydroxyphenyl)methane, tris(hydroxyphenyl)ethane, as well as the alkoxylated derivatives thereof and mixtures thereof.

10. The composition of any one of claims 1-9, wherein R3comprises a residue of a fatty acid dimer and a residue of a fatty acid trimer; in particular, R3comprises a residue of a non-hydrogenated fatty acid dimer and a residue of a non-hydrogenated fatty acid trimer.

11. The composition of any one of claims 1-10, wherein part of the R3groups are independently according to the following formula (30) and the remaining part of the R3groups are independently according to the following formula (3 la) or (3 lb):whereinR1, R2and R4are as defined in any one of claims 1-10;D is a substituted or unsubstituted aliphatic, aryl, or heteroaryl divalent moiety having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms;T is a substituted or unsubstituted aliphatic, aryl, or heteroaryl trivalent moiety having at least 10, preferably at least 15, more preferably at least 21, more preferably at least 24 carbon atoms, and most preferably at least 30 carbon atoms.

12. The composition of claim 11, wherein D corresponds to the residue obtained by removing the COOH groups of a fatty acid dimer, preferably a fatty acid dimer having 32 to 40, preferably 34 to 38, more preferably 36 carbon atoms.

13. The composition of claim 11 or 12, wherein T corresponds to the residue obtained by removing the COOH groups of a fatty acid trimer, preferably a fatty acid trimer having 48 to 60, preferably 51 to 57, more preferably 54 carbon atoms.

14. A polyester compound which the reaction product of:(i) at least one substituted or unsubstituted aliphatic, aryl, aralkyl, alkaryl, heteroaralkyl, alkheteroaryl, or heteroaryl diol, polyol, diepoxide or polyepoxide;(ii) at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl diacid;(iii) at least one substituted or unsubstituted aliphatic, aryl, or heteroaryl triacid; and(iv) at least one ethylenically unsaturated monoacid and / or at least one ethylenically unsaturated monoepoxide.wherein the weight ratio of component (ii) to component (iii) is less than 30:1, preferably between 30:1 and 4.1:1, more preferably between 25:1 and 4.2:1, most preferably between 20:1 and 4.3:1; andthe reaction mixture used to obtain the polyester compound comprises less than 3% preferably less than 2.5 wt.%, more preferably less than 2 wt.%, of monoacid other than (meth)acrylic acid based on the total weight of the reactive species.

15. The compound of claim 14, wherein the reaction mixture used to obtain the polyester compound contains less than 1.8%, less than 1.5%, less than 1.2%, less than 1 wt.%, less than 0.9% or even less than 0.5 wt.%, of monoacid other than (meth)acrylic acid based on the total weight of the reactive species.

16. The compound of claim 14 or 15, wherein component (i) comprises or consists of at least one compound selected from a diol, a polyol having at least three OH groups and mixtures thereof; in particular, component (i) comprises or consists of at least one compound selected from a diol, apolyol having 3 to 6 OH groups and mixtures thereof; more particularly, component (i) comprises or consists of at least one compound selected from a diol, a polyol having 3 or 4 OH groups, and mixtures thereof.

17. The compound of any one of claims 14-16, wherein component (i) comprises or consists of at least one diol or a mixture of at least one diol and at least one polyol having at least 3, in particular 3 to 6, more particularly 3 or 4, OH groups.

18. The compound of any one of claims 14-17, wherein component (i) comprises or consists of at least one diol selected from:- a cyclic diol, in particular a cyclic diol selected from hydroquinone, hydroquinone bis(2-hydroxyethyl) ether, bisphenol-A, B, F or S, bis-ethylene glycol terephthalate, pyrocatechol, resorcinol, cardol, cyclohexanediol, cyclohexane dimethanol, norbomene dimethanol, norbornane dimethanol, tricyclodecanediol, tricyclodecanedimethanol, dicyclopentadiene diol, hydrogenated bisphenol-A, B, F or S, a dianhydrohexitol, as well as the alkoxy lated derivatives thereof;- a diol comprising an ester bond, in particular neopentyl glycol mono(hydroxypivalate) having the following structure:and mixtures thereof.

19. The compound of any one of claims 14-17, wherein component (i) comprises or consists of a mixture of at least one diol and at least one polyol having at least 3 OH groups, in particular 3 to 6 OH groups, more particularly 3 or 4 OH groups.

20. The compound of claim 19, wherein the molar ratio of the at least one diol to the at least one polyol having at least 3 OH groups may be from 1 to 50, preferably from 2 to 25, more preferably from 5 to 20.

21. The compound of claim 19 or 20, wherein the at least one diol is selected from ethylene glycol, propanediols, butanediols, pentanediols, hexanediols, octanediols, decanediols, dodecanediols, 2-methyl-1,3-propanediol, 2-methyl-2,4-pentanediol, neopentyl glycol, 2,2-diethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 3,3-dimethyl-1,5-pentanediol, 2,4-diethyl-1,5-pentanediol, 3,3-butylethyl-1,5-pentane diol, neopentyl glycol mono(hydroxypivalate), di-, tri- or tetra(ethylene glycol), di-, tri- or tetra(l,2-propylene glycol), di-, tri- or tetra(l,3-propylene glycol), di-, tri- or tetra(l,4-butylene glycol), a polyethylene glycol), a polypropylene glycol), a poly(trimethylene glycol), a poly(tetramethylene glycol), a polyethylene glycol-co-propylene glycol, hydroquinone,hydroquinone bis(2 -hydroxyethyl) ether, bisphenol-A, B, F or S, bis-ethylene glycol terephthalate, pyrocatechol, resorcinol, cardol, cyclohexanediol, cyclohexane dimethanol, norbornene dimethanol, norbornane dimethanol, tricyclodecanediol, tricyclodecanedimethanol, dicyclopentadiene diol, hydrogenated bisphenol-A, B, F or S, a dianhydrohexitol, as well as the alkoxylated derivatives thereof and mixtures thereof.

22. The compound of any one of claims 19-21, wherein the at least one polyol having at least three OH groups is selected from trimethylolmethane, trimethylolethane, trimethylolpropane, di(trimethylolpropane), triethylolpropane, pentaerythritol, di(pentaerythritol), tri(pentaerythritol), glycerol, di-, tri- or tetraglycerol, a polyglycerol, an alditol, tris(2-hydroxyethyl)isocyanurate, phloroglucinol, pyrogallol, tris(hydroxyphenyl)methane, tris(hydroxyphenyl)ethane, as well as the alkoxylated derivatives thereof and mixtures thereof.

23. The compound of any one of claims 14-22, wherein component (ii) comprises or consists of at least one fatty acid dimer and component (iii) comprises or consists of at least one fatty acid trimer.

24. The compound of claim 23, wherein the at least one fatty acid dimer is a fatty acid dimer having 32 to 40, preferably 34 to 38, more preferably 36 carbon atoms.

25. The compound of claim 23 or 24, wherein the at least one fatty acid trimer is a fatty acid trimer having 48 to 60, preferably 51 to 57, more preferably 54 carbon atoms.

26. Use of the composition of any of claims 1-13 or the compound of any one of claims 14-25, in a formulation for an adhesive, a coating or an ink, or as a constituent of a solvent-resistant encapsulant formulation, such as a coating for batteries.

27. A curable composition, comprising the composition of any one of claims 1-13 or the compound of any one of claims 14-25, and at least one or more of the following:a. a polymerizable component comprising one or more ethylenically unsaturated compounds and / or one or more cationically polymerizable compounds distinct from the composition of any one of claims 1-13 or the polyester compound of any one of claims 14-25;b. an inhibitor;c. an initiator selected from a free radical initiator, a cationic initiator, and mixtures thereof; and / or d. an additive selected from the group consisting of antioxidants, ultraviolet absorbers, photostabilizers, foam inhibitors, flow or leveling agents, colorants, pigments, dispersants (wetting agents), slip additives, fdlers, thixotropic agents, matting agents, waxes, any additive conventionally utilized in coating, sealant, adhesive, ink or molding compositions, and mixtures thereof.

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