Curable composition

Abstract

The present invention pertains to a composition suitable for coatings and adhesives comprising sustainable components such as epoxidized vegetable oil, the method of preparing the same and applications thereof.

Description

[0001] CURABLE COMPOSITION

[0002] Technical Field

[0003] The invention relates to a composition suitable for coatings and adhesives comprising sustainable components such as epoxidized vegetable oil, the method of preparing the same and applications thereof.

[0004] Technological Background

[0005] There is significant interest in transitioning from non-renewable fossil derived polymeric materials to those derived from renewable sources. Biopolymers, whereby carbon content is derived from CO2 fixed by plants or other photosynthetic organisms, offer an interesting alternative.

[0006] Within the textile (e.g. leather and cotton woven textile) manufacturing sectors, natural materials are often combined with synthetic polymeric materials such as coatings, adhesives, resins, or other modifying agents. For creating products substantially free from fossil derived materials, it is aimed at replacing said materials with biopolymer alternatives.

[0007] One class of biopolymers are those derived from epoxidized natural molecules, such as triglycerides, phenolic compounds, polyalcohols and polyisoprene. These epoxidized molecules can be reacted with so called hardeners to build larger molecular weight entities. If both the epoxy component and the hardener are multi-functional, 3D polymer networks may be formed.

[0008] Traditional epoxy-based materials combine a petroleum derived multi-functional epoxy (e.g. Bisphenol A diglycidyl ether - DGEBA) with a petroleum derived multi-functional hardener (e.g. Triethylenetetramine - TETA) to create polymeric materials with high cross-linking density. The resulting materials are stiff, and show good chemical and water resistance, resulting in their application in hard-wearing industrial applications such as marine coatings. High cross-linking density can however lead to materials with high brittleness and low toughness. 100% bio-based epoxies tend to have significantly reduced glass-transition temperature (Tg), increased flexibility and reduced strength. Given the existing applications of epoxy resins, literature typically focusses on either a) blending bio-based resins with petroleum derived resins to improve petroleum resin toughness and bio-based content, or b) selecting curatives that give the highest crosslinking density. Additional challenges with bio-based materials include strong odours, and colouration of the final material.

[0009] Within certain applications, such as textile coatings however, flexibility is a desirable characteristic for both coatings and adhesives.

[0010] Against this background, it is an object of the present invention to provide a composition, preferably a homogeneous composition, that is stable at room temperature and / or easily cures when applying increased temperature. It is a further object of the present invention to provide a bio-based, preferably 100% bio-based, composition that is suitable for coating, preferably textile coating, and / or adhesive applications. It is a further object of the present invention to provide a bio-based, preferably 100% bio-based, composition that can replace synthetic materials such as polyurethane, silicones, and PVC. It is a further object of the present invention to provide a composition having no unpleasant odour and / or reducing undesired colouration that is suitable for coating, preferably textile coating, and / or adhesive applications. It is a further object of the present invention to provide an efficient method of preparing such compositions. It is a further object of the present invention to provide a method of curing such compositions. It is a further object of the present invention to provide suitable applications of curable compositions such as coated textiles.

[0011] Summary of the invention

[0012] In a first aspect, the invention relates to a composition comprising i) at least one epoxidized vegetable oil (EVO) and ii) an intermediate oligomer (IO) comprising at least one primary amine group and at least one hydroxyl group.

[0013] According to a second aspect, the invention relates to a method of preparing a composition comprising the step of a) mixing an epoxy compound (EC) comprising at least one terminal epoxy group with an amine compound (AC) comprising at least one primary amine group to provide an intermediate oligomer (IO) and b) mixing said intermediate oligomer (10) with at least one epoxidized vegetable oil (EVO).

[0014] According to a third aspect, the invention relates to a composition obtained by the method according to the second aspect.

[0015] According to a fourth aspect, the invention relates to a method for curing a composition, comprising i-1) providing the composition according to the first or fourth aspect; i-2) optionally heating the composition of step i-1) to a temperature of at least about 40 °C for at least about 5 minutes; and ii) curing the optionally heated composition at a temperature of at least about 50 °C.

[0016] According to a fifth aspect, the invention relates to the use of the composition according to the first or fourth aspect to increase hydrophobicity of a substrate’s surface, preferably of a textile’s surface.

[0017] According to a sixth aspect, the invention relates to an adhesive comprising the composition according to the first or fourth aspect.

[0018] According to a seventh aspect, the invention relates to the use of a mixture comprising at least one epoxidized vegetable oil (EVO) and at least one amine compound (AC) comprising at least two primary amine groups as a textile coating.

[0019] It has surprisingly been found that the inventive composition and methods solve at least one of the above needs and that the present invention provides inter alia an environmentally and / or economically friendly approach to preplace synthetic materials. In addition, the cured compositions provide suitable properties for coatings and / or adhesives.

[0020] Detailed description of the invention

[0021] Brief description of the drawing

[0022] The present disclosure will be more readily appreciated by reference to the following detailed description when being considered in connection with the accompanying drawing in which:

[0023] Figure 1 (Fig. 1) discloses the hydrophobicity test according to Example 6.3. Row A) discloses the hydrophobicity of a not treated cotton woven textile, wherein the water droplet was absorbed within 10 seconds, whereas the water droplets on the coated cotton woven textile remained on surface for more than 10 minutes (row B)).

[0024] Definitions

[0025] The term "substituted" as used herein, means that a hydrogen atom bonded to a designated atom is replaced with a specified substituent, provided that the substitution results in a stable or chemically feasible compound. Unless otherwise indicated, a substituted atom may have one or more substituents and each substituent is independently selected.

[0026] When it is referred to certain atoms or moieties being substituted with "one or more" substituents, the term "one or more" is intended to cover at least one substituent, e.g. 1 to 10 substituents, preferably 1 , 2, 3, 4 or 5 substituents, more preferably 1 , 2, or 3 substituents, most preferably 1 or 2 substituents. When neither the term "unsubstituted" nor "substituted" is explicitly mentioned concerning a moiety, said moiety is to be considered as unsubstituted.

[0027] The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group.

[0028] The term "halogen" denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine, or bromine.

[0029] The term "alkyl" as used herein denotes in each case a straight-chain or branched alkyl group having usually from 1 to 20 carbon atoms, such as 1 to 4 carbon atoms, preferably 1 to 3 or 1 or 2 carbon atoms. Examples of an alkyl group are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl, iso-butyl, tert-butyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-di-methylpropyl, 1- ethylpropyl, n-hexyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethyl-butyl, 2,2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1-ethyl-1 -methylpropyl, and 1-ethyl-2-methylpropyl.

[0030] The term "alkoxy" as used herein denotes in each case a straight-chain or branched alkyl group which is bonded via an oxygen atom and has usually from 1 to 20 carbon atoms, such as 1 to 2 carbon atoms, preferably 1 carbon atom. Examples of an alkoxy group are methoxy, ethoxy, n- propoxy, iso-propoxy, n-butyloxy, 2-butyloxy, iso-butyloxy, tert.-butyloxy, and the like. The term “carbocyclyl” (alternatively also referred to as "carbocycle") includes, unless otherwise indicated, in general a 3- to 9-membered, preferably a 4- to 8-membered or a 3- to 6-membered or a 5- to 7-membered, more preferably a 5- or 6-membered monocyclic ring comprising 3 to 9, preferably 4 to 8 or 3 to 6 or 5 to 7, more preferably 5 or 6 carbon atoms. The carbocycle may be saturated, partially or fully unsaturated, or aromatic, wherein saturated means that only single bonds are present, and partially or fully unsaturated means that one or more double bonds may be present in suitable positions, while the Huckel rule for aromaticity is not fulfilled, whereas aromatic means that the Huckel (4n + 2) rule is fulfilled. The term "carbocyclyl", unless otherwise indicated, may therefore cover inter alia cycloalkyl, cycloalkenyl, as well as phenyl. Preferably, the term "carbocyclyl" covers cycloalkyl and cycloalkenyl groups, for example cyclopropane, cyclobutane, cyclopentane and cyclohexane rings.

[0031] The term "heterocyclyl" includes, unless otherwise indicated, in general a 3- to 9-membered, preferably a 4- to 8-membered or 5- to 7-membered, more preferably 5- or 6-membered, in particular 6-membered monocyclic ring. The heterocycle may be saturated, partially or fully unsaturated, or aromatic, wherein saturated means that only single bonds are present, and partially or fully unsaturated means that one or more double bonds may be present in suitable positions, while the Huckel rule for aromaticity is not fulfilled, whereas aromatic means that the Huckel (4n + 2) rule is fulfilled. The heterocycle typically comprises one or more, e.g. 1 , 2, 3, or 4, preferably 1 , 2, or 3 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO2. The remaining ring members are carbon atoms. In a preferred embodiment, the heterocycle is an aromatic heterocycle, preferably a 5- or 6-membered aromatic heterocycle comprising one or more, e.g. 1 , 2, 3, or 4, preferably 1 , 2, or 3 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO2. Examples of 5- or 6-membered aromatic heterocycles include pyridyl (also referred to as pyridinyl), i.e. 2-, 3-, or4-pyridyl, pyrimidinyl, i.e. 2-, 4- or 5-pyrimidinyl, pyrazinyl, pyridazinyl, i.e. 3- or 4-pyridazinyl, thienyl, i.e. 2- or 3-thienyl, or furyl, i.e. 2-or 3-furyl, pyrrolyl, i.e. 2- or 3-pyrrolyl. The saturated or partially or fully unsaturated heterocycles usually comprise 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO2. The skilled person is aware that S, SO or SO2 is to be understood as follows: The term “bivalent” as used herein denotes that the respective moiety comprises at least two substituents. The respective moiety may additionally independently be substituted or unsubstituted such as with RAas further disclosed herein. Examples for bivalent moieties are furanylene, phenylene, and cyclohexylene, which may further be substituted.

[0032] It is to be understand that denotes the bond of the respective moiety to the remainder of the molecule.

[0033] As used in the specification and the claims, the singular forms of "a" and "an" also include the corresponding plurals unless the context clearly dictates otherwise. The same applies for plural forms used herein, which also include the singular forms unless the context clearly dictates otherwise.

[0034] The terms "about" and "approximately" in the context of the present invention denotes an interval of accuracy that a person skilled in the art will understand to still ensure the technical effect of the feature in question. The term typically indicates a deviation from the indicated numerical value of ±10% and preferably ±5% such as ±2% or ±1%.

[0035] It needs to be understood that the term "comprising" is not limiting. For the purposes of the present invention, the term "consisting of is considered to be a preferred embodiment of the term "comprising of. If hereinafter a group is defined to comprise at least a certain number of embodiments, this is also meant to encompass a group, which preferably consists of these embodiments only.

[0036] The term “bio-based” as used herein denotes a product derived from biomass, wherein the biomass is suitable a total mass of living organisms of vegetable or animal origin in a defined environment, called biotope, and the resources resulting therefrom through direct, indirect or potential use for humanity. Suitably, the carbon atoms of a bio-based material are at least about 70%, preferably at least about 80%, more preferably at least about 90%, even more preferably at least about 95% or at least about 98%, or about 100% derived from biomass.

[0037] Detailed description of embodiments

[0038] As indicated above, in a first aspect, the present invention relates to a composition comprising i) at least one epoxidized vegetable oil (EVO) and ii) an intermediate oligomer (IO) comprising at least one primary amine group and at least one hydroxyl group. In the following, embodiments of the present invention such as ingredients and moieties are described in further details. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments.

[0039] In some embodiments, the at least one epoxidized vegetable oil is selected from the group consisting of epoxidized coconut oil, epoxidized corn oil, epoxidized cottonseed oil, epoxidized olive oil, epoxidized palm oil, epoxidized peanut oil, epoxidized rapeseed oil, epoxidized safflower oil, epoxidized sesame oil, epoxidized soybean oil, epoxidized sunflower oil, epoxidized linseed oil, epoxidized chia seed oil, epoxidized algal oil, epoxidized jatropha oil, and combinations thereof, preferably selected from the group consisting of epoxidized rapeseed oil, epoxidized soybean oil, epoxidized linseed oil, epoxidized palm oil, epoxidized chia seed oil, and combinations thereof, more preferably epoxidized linseed oil.

[0040] In some embodiments, the at least one epoxidized vegetable oil has a molecular weight of about 600 to about 2,000 g / mol, preferably of about 700 to about 1 ,500 g / mol, more preferably of about 800 to about 1 ,200 g / mol such as of about 850 to about 1 ,100 g / mol, or of about 900 to about 1 ,000 g / mol. In general, the molecular weight can be determined according to known in the art methods such as using gel permeation chromatography (GPC).

[0041] In some embodiments, the at least one epoxidized vegetable oil has about 2 to about 10, preferably about 3 to about 8, more preferably about 4 to about 7 such as about 5 to about 6, epoxy groups.

[0042] In some embodiments, one or more epoxy group(s) of the at least one epoxidized vegetable oil has been converted to a carbonate group. Such carbonate groups are suitably obtained by reacting an epoxy group with carbon dioxide, optionally in the presence of a catalyst. In some embodiments, the at least one epoxidized vegetable oil comprises one or more carbonate group, preferably one or more cyclic carbonate group. The skilled person is aware that said cyclic carbonate group is to be understood as follows: Without wishing to be bound by theory, it is believed that epoxidized vegetable oil, wherein one or more epoxy group(s) has been converted to a carbonate group, may be a suitable starting material of non-isocyanate polyurethanes.

[0043] In some embodiments, the intermediate oligomer (IO) comprises a functionality selected from the group consisting of secondary amine, ether, (bivalent) carbocyclyl, (bivalent) heterocyclyl, and combinations thereof. Each carbon atom of the aforementioned (bivalent) carbocyclyl or (bivalent) heterocyclyl functionality can be independently substituted or unsubstituted with RA, wherein RAis independently C1-C20-alkyl, C1-C20-alkoxy, or halogen.

[0044] In some embodiments, RAis independently C1 -C18-alkyl, C1-C18-alkoxy, or halogen, preferably is independently C1 -C14-alkyl, C1-C14-alkoxy, or halogen, such as is independently C1 -C12-alkyl, C1-C12-alkoxy, or halogen, or is independently C1 -C10-alkyl, C1-C10-alkoxy, or halogen, or is independently C1-C8-alkyl, C1-C8-alkoxy, or halogen, or is independently C1-C6-alkyl, C1-C6- alkoxy, or halogen, or is independently C1-C4-alkyl, C1-C4-alkoxy, F, Cl, or Br, or is independently C1-C2-alkyl, C1-C2-alkoxy, or F.

[0045] In some embodiments, the intermediate oligomer (IO) comprises a functionality having formula

[0046] (A-1) (A-1), preferably having formula (A-2)H(A-2).

[0047] In some embodiments, the intermediate oligomer (IO) has a viscosity of about 500 to about 6,000 mPa s, preferably of about 800 to about 5,000 mPa s, or of about 1 ,000 to about 4,000 mPa s, or of about 1 ,500 to about 3,500 mPa s, or of about 1 ,800 to about 3,000 mPa s, or of about 2,000 to about 2,500 mPa s. In general, the viscosity can be determined according to known in the art methods suitably via Brookfield viscosity such as measuring in BROOKFIELD AMETEK DVNext using spindle 21 , 27 and 29 at room temperature.

[0048] In some embodiments, the intermediate oligomer (IO) has a molecular weight of about 500 to about 20,000 g / mol, preferably of about 700 to about 15,000 g / mol, more preferably of about 900 to about 10,000 g / mol, or of about 1 ,000 to about 5,000 g / mol, or of about 3,000 to about 8,000 g / mol.

[0049] In some embodiments, the intermediate oligomer (IO) is obtainable, preferably is obtained, by a reaction of an epoxy (EC) compound comprising at least one terminal epoxy group with an amine compound (AC) comprising at least one, preferably at least two, primary amine group. In some embodiments, the epoxy compound (EC) comprises at least one hydroxyl group, preferably comprises one to five, such as one, two, or three, hydroxyl groups.

[0050] In some embodiments, in said reaction the weight amount of the epoxy compound (EC) is of about 1 to about 20 wt.-%, preferably of about 2 to about 15 wt.-%, more preferably of about 3 to about 10 wt.-% such as about 4 to about 8 wt.-%, based on the combined weight of the amine compound (AC) and the epoxy compound (EC).

[0051] In some embodiments, the epoxy compound (EC) comprises at least two terminal epoxy groups such as at least three, or at least four, or at least five, or at least six, terminal epoxy groups. Suitably, the epoxy compound (EC) comprises two to ten, preferably two to eight, more preferably two to seven such as two to six, or two to five, or two to four such as two, three, or four terminal epoxy groups.

[0052] In some embodiments, the epoxy compound (EC) comprises at least one, preferably at least two such as at least three, or at least four, or at least five, or at least six, or at least seven, or at least eight, or at least nine, or at least ten, ether functionalities. Suitably, the epoxy compound (EC) comprises two to 15, preferably two to ten, such as two, three, four, five, six, seven, eight, nine, or ten ether functionalities. In this connection, the ether functionality as used herein is considered being different to an epoxy group, i.e. that no three-membered ring is being formed.

[0053] In some embodiments, the epoxy compound (EC) comprises at least one, preferably at least two such as two to ten, or two to six, or two to five, glycidyl ether groups.

[0054] In some embodiments, the epoxy compound (EC) is selected from the group consisting of , and combinations thereof.

[0055] In some embodiments, the amine compound (AC) comprising at least two such as at least three or at least four, primary amine groups. Suitably, the amine compound (AC) comprising two to five, such as two, three, or four, preferably two primary amine groups.

[0056] In some embodiments, the amine compound (AC) is a bio-based amine. In some embodiments, the amine compound (AC) is derived from fatty acids. In this connection, it is to be understood that in an amine compound (AC) that is derived from a fatty acid, the carboxylic acid group is replaced by a primary amine group.

[0057] In some embodiments, the amine compound (AC) is derived from dimerized fatty acids (also referred to as fatty acid dimer). In some embodiments, the amine compound (AC) comprises two primary amine group derived from a fatty acid dimer.

[0058] In some embodiments, the amine compound (AC) is derived from trimerized fatty acids.

[0059] In some embodiments, the amine compound (AC) comprises the amine form of a dimerized fatty acid and optionally the amine form of a trimerized fatty acid.

[0060] In some embodiments, the amine compound (AC) comprising at least one functionality selected from the group consisting of (bivalent) carbocyclyl, (bivalent) heterocyclyl, secondary amine, and combinations thereof, wherein each carbon atom of the aforementioned (bivalent) carbocyclyl or (bivalent) heterocyclyl, functionality is independently substituted or unsubstituted with RA, wherein RAis independently C1-C20-alkyl, C1-C20-alkoxy, or halogen.

[0061] In some embodiments, the amine compound (AC) comprises from 4 to 50 carbon atoms, preferably from 10 to 45 carbon atoms, more preferably from 20 to 40 carbon atoms such as from 25 to 40 carbon atoms, or from 30 to 40 carbon atoms. The amine compound (AC) may exemplarily comprise 36 carbon atoms.

[0062] In some embodiments, the amine compound (AC) comprises two primary amine groups that are connected via 3 to 40, preferably via 4 to 30, more preferably via 5 to 20 such as via 10 to 20, or via 15 to 20, adjacent carbon atoms.

[0063] In some embodiments, the amine compound (AC) comprises a functionality selected from the group consisting of bivalent heterocyclyl, bivalent aryl, bivalent saturated carbocyclyl, secondary amine, and combinations thereof, preferably selected from the group consisting of furanylene, phenylene, cyclohexylene, secondary amine, and combinations thereof, wherein each carbon atom of the aforementioned functionalities is independently substituted or unsubstituted with RA, wherein RAis independently C1 -C10-alkyl, C1-C10-alkoxy, or halogen.

[0064] In some embodiments, the amine compound (AC) is selected from the group consisting of aliphatic, preferably bio-based, multi-functional amines (e.g. 1 ,3-diaminopropane, 1 ,4-diaminobutane, 1 ,5 diaminopentane, 1 ,6-diaminohexane, 1 ,8-diaminoctane, 1 ,10-diaminodecane, 1 ,12- diaminododecane, other amino-acid derivatives from lysine, arginine, orthonine, glutamine, histidine and tryptophan, other multi-functional amines derived from di / trimerization of fatty acids e.g. C36 diamines), aromatic, preferably bio-based, multi-functional amines (e.g. furan based diamines, those derived from lignin, those derived from cashew nut shell liquid), and combinations thereof. In this connection, a multi-functional amine is considered to comprise at least two primary amine groups.

[0065] In some embodiments, the amine compound (AC) is selected from the group consisting 1 ,4- diaminobutane, 1 ,5-diamino pentane, multi-functional amines derived from fatty acids (e.g. derived from a C36 dimer acid such as is the case for Priamine™ 1071), and combinations thereof, preferably multi-functional amines derived from fatty acids.

[0066] In some embodiments, the amine compound (AC) is selected from the group consisting of combinations thereof, wherein n and m are each independently selected from 1 to 12.

[0067] In some embodiments, the amine compound (AC) has a molecular weight of about 80 to about 2,000 g / mol, preferably of about 200 to about 1 ,500 g / mol, more preferably of about 300 to about 1 ,000 g / mol, or of about 400 to about 800 g / mol.

[0068] In some embodiments, the amine compound (AC) has an amine value of about 50 to about 800 mgKOH / g, preferably about 100 to about 600 mgKOH / g, more preferably of about 150 to about 400 mgKOH / g such as of about 160 to about 300 mgKOH / g or of about 180 to about 250 mgKOH / g.

[0069] In some embodiments, the amine compound (AC) is derived from, preferably is, a compound of formula (AC-1) to 12, preferably from 2 to 10 such as from 2, 3, 4, 5, 6, or 7.

[0070] In some embodiments, the amine compound (AC) is derived from, preferably is,

[0071] As indicated above, the present invention relates in a second aspect to a method of preparing a composition comprising the step of a) mixing an epoxy compound (EC) comprising at least one terminal epoxy group with an amine compound (AC) comprising at least one primary amine group to provide an intermediate oligomer (IO) and b) mixing said intermediate oligomer (IO) with at least one epoxidized vegetable oil (EVO).

[0072] Embodiments (e.g. regarding the ingredients and moieties) are already above-outlined in connection with the inventive composition and shall hold for the method, as well. In the following, embodiments of the methods are described in further detail. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments.

[0073] In some embodiments, in step a), the amine compound (AC) is applied in excess over the epoxy compound (EC), preferably wherein the weight amount of the epoxy compound (EC) is of about 1 to about 20 wt.-%, preferably of about 2 to about 15 wt.-%, more preferably of about 3 to about 10 wt.- %, based on the combined weight of the amine compound (AC) and the epoxy compound (EC).

[0074] In some embodiments, in step a), the molar ratio of the amine groups to the epoxy groups is of about 1 :2 to about 20:1 , preferably of about 1 :1 to about 18:1 , more preferably of about 2:1 to about 16:1 , even more preferably of about 3:1 to about 14:1 , or of about 4:1 to about 13:1 , or of about 5:1 to about 12:1 , or of about 6:1 to about 11 :1 , or of about 7:1 to about 10:1 , or of about 8:1 to about 9:1. In some embodiments, the at least one epoxidized vegetable oil (EVO) is selected from the group consisting of epoxidized rapeseed oil, epoxidized soybean oil, epoxidized linseed oil, epoxidized palm oil, epoxidized chia seed oil, and combinations thereof, preferably epoxidized linseed oil.

[0075] In some embodiments, step a) is conducted at about 0 to about 100 °C, preferably at about 10 to about 80 °C, or at about 20 to about 60 °C, or at about 20 to about 40 °C, or at about 30 to about 60 °C.

[0076] In some embodiments, step a) is conducted for about 1 to about 40 hours, preferably for about 2 to about 30 hours, or for about 2 to about 10 hours, or for about 15 to about 26 hours.

[0077] In some embodiments, step a) is conducted at about 20 to about 40 °C for about 2 to about 26 hours such as for about 2 to about 10 hours or for about 15 to about 26 hours.

[0078] In some embodiments, step a) is conducted at about 20 to about 60 °C such as at about 20 to about

[0079] 40 °C or at about 30 to about 60 °C for about 2 to about 10 hours.

[0080] In some embodiments, the epoxy compound (EC) comprises at least two terminal epoxy groups such as at least three, or at least four, or at least five, or at least six, terminal epoxy groups. Suitably, the epoxy compound (EC) comprises two to six, preferably two to five such as two, three, four, or five terminal epoxy groups.

[0081] In some embodiments, the epoxy compound (EC) comprises at least one, preferably at least two such as at least three, or at least four, or at least five, or at least six, or at least seven, or at least eight, or at least nine, or at least ten, ether functionalities.

[0082] In some embodiments, the epoxy compound (EC) comprises at least one hydroxyl group, preferably comprises one to five, such as one, two, or three, hydroxyl groups.

[0083] In some embodiments, the epoxy compound (EC) comprises at least one, preferably at least two such as two to ten, or two to six, or two to five, glycidyl ether groups.

[0084] In some embodiments, the epoxy compound (EC) is selected from the group consisting of , , and combinations thereof. In some embodiments, the amine compound (AC) comprising at least two such as at least three or at least four, primary amine groups. Suitably, the amine compound (AC) comprising two to five, such as two, three, or four, preferably two primary amine groups.

[0085] In some embodiments, the amine compound (AC) is a bio-based amine.

[0086] In some embodiments, the amine compound (AC) is derived from fatty acids.

[0087] In some embodiments, the amine compound (AC) is a derived from dimerized fatty acids. In some embodiments, the amine compound (AC) comprises two primary amine group derived from a fatty acid dimer.

[0088] In some embodiments, the amine compound (AC) comprising at least one functionality selected from the group consisting of (bivalent) carbocyclyl, (bivalent) heterocyclyl, secondary amine, and combinations thereof, wherein each carbon atom of the aforementioned (bivalent) carbocyclyl or (bivalent) heterocyclyl, functionality is independently substituted or unsubstituted with RA, wherein RAis independently C1-C20-alkyl, C1-C20-alkoxy, or halogen.

[0089] In some embodiments, the amine compound (AC) comprises from 4 to 50 carbon atoms, preferably from 10 to 45 carbon atoms, more preferably from 20 to 40 carbon atoms such as from 25 to 40 carbon atoms, or from 30 to 40 carbon atoms. The amine compound (AC) may exemplarily comprise 36 carbon atoms.

[0090] In some embodiments, the amine compound (AC) comprises two primary amine groups that are connected via 3 to 40, preferably via 4 to 30, more preferably via 5 to 20 such as via 10 to 20, or via 15 to 20, adjacent carbon atoms.

[0091] In some embodiments, the amine compound (AC) has a molecular weight of about 80 to about 2,000 g / mol, preferably of about 200 to about 1 ,500 g / mol, more preferably of about 300 to about 1 ,000 g / mol, or of about 400 to about 800 g / mol.

[0092] In some embodiments, the amine compound (AC) is derived from, preferably is, a compound of formula (AC-1) (AC-1), wherein n and m are each independently selected from 1 to 12, preferably from 2 to 10 such as from 2, 3, 4, 5, 6, or 7. In some embodiments, the amine compound (AC) is derived from, preferably is,

[0093] In some embodiments, the amine compound (AC) is at about 1 bar and at about 25 °C a liquid.

[0094] As indicated above, the present invention relates in a third aspect to a composition obtained by the method according to the second aspect.

[0095] Embodiments (e.g. regarding the ingredients, moieties, functionalities, reaction conditions) are already above-outlined in connection with the inventive composition / method and shall hold for the third aspect, as well.

[0096] As indicated above, the present invention relates in a fourth aspect to a method for curing a composition, comprising i-1) providing the composition according to the first or the third aspect; i-2) optionally heating the composition of step i-1) to a temperature of at least about 40 °C for at least about 5 minutes; and ii) curing the optionally heated composition at a temperature of at least about 50 °C.

[0097] Embodiments (e.g. regarding the ingredients, moieties, functionalities, reaction conditions) are already above-outlined in connection with the first to third aspect and shall hold for the fourth aspect, as well. In the following, embodiments of the methods are described in further detail. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments.

[0098] In some embodiments, the composition of step i-1) is not further heated. In some embodiments, the composition of step i-1) stirred at room temperature (such as at about 18 to about 25 °C) for about 1 to about 24 hours, preferably for about 2 to about 18 hours, such as for about 2 to about 5 hours or for about 10 to about 18 hours. In some embodiments, step i-2) is conducted at a temperature of at least about 50 °C, preferably at a temperature of about 50 to about 200 °C, or of about 70 to about 100 °C or of about 100 to about 150 °C.

[0099] In further embodiments, step i-2) is conducted for at least about 30 minutes, preferably for at least about 60 minutes, more preferably for about 1 to about 10 hours or for about 1 to about 5 hours such as for about 2 to about 4 hours.

[0100] In other embodiments, step i-2) is not conducted.

[0101] In some embodiments, step ii) is conducted at a temperature of at least about 100 °C, preferably at least about 130 °C, more preferably at a temperature of about 130 to about 300 °C, or of about 150 to about 250 °C, or of about 180 to about 220 °C.

[0102] In some embodiments, step ii) is conducted for at least about 30 minutes, preferably for at least about 60 minutes, more preferably for about 1 to about 5 hours such as for about 1 to about 4 hours, or for about 1 to about 3 hours.

[0103] In some embodiments, the method provides a cured film having a tensile strengths (o) of at least about 1 MPa, preferably of at least about 3 MPa, more preferably of at least about 5 MPa, and even more preferably of at least about 10 MPa.

[0104] In some embodiments, the method provides a cured film having an elongation at break (e) of at least about 25%, preferably of at least about 30%, more preferably of at least about 35%, even more preferably of at least about 40%. Suitably, the method provides a cured film having an elongation at break (e) of up to about 100% or about 90%.

[0105] In some embodiments, the method further comprises the steps of i-3) applying the optionally heated composition (i.e. the composition of step i-1) or of step i-2)) to a substrate; and ii) curing the substrate of step i-3) to obtain a coated substrate.

[0106] In some embodiments, the optionally heated composition is coated on the substrate with a thickness of about 10 to about 400 pm, preferably of about 30 to about 300 pm, more preferably of about 50 to about 200 pm such as of about 80 to about 150 pm.

[0107] In some embodiments, the substrate is a textile. In some embodiments, the textile is selected from the group consisting of cellulosic textiles, cotton, linen, silk, wool, polyester, rayon, velour, leather and synthetic leather, preferably selected from the group consisting of cotton, leather and synthetic leather.

[0108] In some embodiments, the substrate may be a backing layer to create a coated material, which may serve as a substitute for natural animal-hide leather.

[0109] As indicated above, the present invention relates in a fifth aspect to of the use of the composition according to the first or the third aspect to increase hydrophobicity of a substrate’s surface.

[0110] Embodiments (e.g. regarding the ingredients, moieties, functionalities, reaction conditions) are already above-outlined in connection with the first to fourth aspect and shall hold for the fifth aspect, as well. In the following, embodiments of the use are described in further detail. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments.

[0111] In some embodiments, the substrate’s surface is a textile’s surface.

[0112] In some embodiments, textile is selected from the group consisting of cellulosic textiles, cotton, linen, silk, wool, polyester, rayon, velour, leather and synthetic leather, preferably selected from the group consisting of cotton, leather and synthetic leather.

[0113] In some embodiments, the substrate may be a backing layer to create a coated material, which may serve as a substitute for natural animal-hide leather.

[0114] As indicated above, the present invention relates in a sixth aspect to an adhesive comprising the composition according to the first or the third aspect.

[0115] Embodiments (e.g. regarding the ingredients, moieties, functionalities, reaction conditions) are already above-outlined in connection with the first to third aspect and shall hold for the sixth aspect, as well. In the following, embodiments of the adhesive are described in further detail. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments.

[0116] In some embodiments, the adhesive comprises at least one additive such as selected from the group consisting of a tackifier, a plasticizer, a rheology modifier, an adhesion promoter, an antioxidant, a filler, a colorant, a surfactant, a catalyst, a solvent, and combinations thereof. The adhesive is suitably applied between two substrates and dried to bind the two substrates together.

[0117] As indicated above, the present invention relates in a seventh aspect to the use of a mixture comprising at least one epoxidized vegetable oil (EVO) and at least one amine compound (AC) comprising at least two primary amine groups as a textile coating.

[0118] Embodiments (e.g. regarding the EVO, AC, coating conditions) are already above-outlined in connection with the first to fourth aspect and shall hold for the sevens aspect, as well. In the following, embodiments of the use are described in further detail. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments.

[0119] In some embodiments, the at least one epoxidized vegetable oil (EVO) is selected from the group consisting of epoxidized rapeseed oil, epoxidized soybean oil, epoxidized linseed oil, epoxidized palm oil, epoxidized chia seed oil, and combinations thereof, preferably epoxidized linseed oil.

[0120] In some embodiments, the weight ratio of the at least one epoxidized vegetable oil (EVO) to the at least one amine compound (AC) is of about 20:1 to about 1 :20, preferably of about 10:1 to about 1 :10, more preferably of about 5:1 to about 1 :5 such as of about 2:1 to about 1 :2 or of about 1 :1.

[0121] In some embodiments, the at least one epoxidized vegetable oil (EVO) and the at least one amine compound (AC) are mixed (e.g. via stirring) for about 10 minutes to about 24 hours, preferably for about 20 minutes to about 16 hours, more preferably for about 30 minutes to about 10 hours such as for about 30 minutes to about 5 hours, or for about 30 minutes to about 2 hours.

[0122] In some embodiments, the at least one epoxidized vegetable oil (EVO) and the at least one amine compound (AC) are mixed (e.g. via stirring) at about 50 to about 200 °C, preferably at about 70 to about 180 °C, more preferably at about 80 to about 160 °C such as at about 90 to about 150 °C, or at about 100 to about 140 °C, or to about 110 to about 130 °C.

[0123] In some embodiments, the mixture is applied onto a textile and heated at a temperature of at least about 100 °C, preferably at least about 130 °C, more preferably at a temperature of about 130 to about 300 °C, or of about 150 to about 250 °C, or of about 180 to about 220 °C. In some embodiments, the mixture is applied onto a textile and heated for at least about 30 minutes, preferably for at least about 60 minutes, more preferably for about 1 to about 5 hours such as for about 1 to about 4 hours, or for about 1 to about 3 hours.

[0124] In some embodiments, the mixture is coated on a textile with a thickness of about 10 to about 400 pm, preferably of about 30 to about 300 pm, more preferably of about 50 to about 200 pm such as of about 80 to about 150 pm.

[0125] In some embodiments, the textile is selected from the group consisting of cotton, linen, silk, wool, polyester, rayon, velour, leather and synthetic leather, preferably selected from the group consisting of cotton, leather and synthetic leather, preferably selected from the group consisting of cotton, leather and synthetic leather.

[0126] In some embodiment, the use is suitable to improve hydrophobicity and / or abrasion resistance and / or flexibility.

[0127] It will be obvious for a person skilled in the art that these embodiments and items only depict examples of a plurality of possibilities. Hence, the embodiments shown here should not be understood to form a limitation of these features and configurations. Any possible combination and configuration of the described features can be chosen according to the scope of the invention.

[0128] Examples

[0129] Materials and Methods

[0130] Priamine™ 1071 was obtained from Cargill and is a dimer diamine having an amine value mgKOH / g of about 205 and having a viscosity of about 3,600 mPa s.

[0131] Denacol GEX-521 was obtained from Nagase ChemteX Corporation and is an epoxy-containing compounds having the structure and a viscosity of about

[0132] 8,300 mPa s.

[0133] Denacol GEX-313 was obtained from Nagase ChemteX Corporation and is an epoxy-containing compounds having the structure

[0134] The epoxidized linseed oil was obtained from HOBUM Oleochemicals GmbH.

[0135] Tensile strength can be determined according to ASTM D638 or ISO 527or by evaluating the film to have 1) very high, 2) high, 3) medium, 4) low, or 5) very low tensile strength.

[0136] Elongation at break (also known as strain at break, is the ratio between changed length and initial length after breakage of the test specimen, i.e. denotes the ability to stretch) can be determined according to ASTM D638 or ISO 527 or by evaluating the film to have 1) very high, 2) high, 3) medium, 4) low, or 5) very low elongation at break. Suitably, a film has an elongation at break of more than about 40% and returns to original shape when stress is removed.

[0137] Unless otherwise indicated, the viscosity was measured in BROOKFIELD AMETEK DVNext using spindle 21 , 27 and 29 at room temperature.

[0138] Tackiness can be determined according to ASTM D3121 or ASTM D6195 or by evaluating the film to have 1) very low, 2) low, 3) medium, 4) high, or 5) very high tackiness. Flexibility (the ability to bend) can be determined according to ISO 178 or by evaluating the film to have 1) very high, 2) high, 3) medium, 4) low, or 5) very low flexibility. For a suitable coating, a film should preferably have a high flexibility.

[0139] Abrasion resistance can be determined by measuring colour fastness of pigmented coatings subjected to wet and dry rubbing, such as in ISO 11640. Abrasion resistance of textiles can be determined by Martindale testing (e.g. ISO 12947).

[0140] Unless noted to the contrary room temperature denotes a temperature of about 18 to about 25 °C such as about 20 °C.

[0141] Comparative Example 1 (cured film)

[0142] A mixture of Priamine™ 1071 (5 g) and epoxidized linseed oil (5 g) was heated at about 60 °C for about 5 minutes. A homogeneous viscous liquid was obtained as a prepolymer. The reaction mixture was poured into a silicon cup and cured at about 200 °C for about 3 h. The curing process yielded a brown film having a high tensile strength and a medium flexibility.

[0143] Comparative Example 2a (cured film)

[0144] Sebacic acid (1 .8 g) (10 wt.-% of acid) was melted at about 140 °C. To that, ELO (1 .2 g) was added and stirred for about 45 minutes at about 140 °C. Additional ELO (15 g) was added to the reaction mixture and further heated at about 140 °C for about 20 minutes. The prepolymer was poured hot into silicon cup. The sample was cured at about 200 °C in a pre-heated oven for about 3 h. The viscous liquid polymerized to a flexible, tacky, and yellow film having a very low tensile strength.

[0145] Comparative Example 2b (cured film)

[0146] Sebacic acid (1 .8 g) (20 wt.-% of acid) was melted at about 140 °C. To that, ELO (1 .2 g) was added and stirred for about 45 minutes at about 140 °C. Additional ELO (6 g) was added to the reaction mixture and further heated at about 140 °C for about 15 minutes. The prepolymer was poured hot into the silicon cup. The sample was cured at about 200 °C in a pre-heated oven for about 2 h. The viscous liquid polymerized to a glassy, yellow cake. The film was less tacky but more rigid than Comparative Example 2a. Comparative Example 3 (coated textile)

[0147] 60 g scale synthesis: Sebacic acid (9 g) (15.2 wt.-% of acid) was melted at about 150 °C (reaction temperature about 110 °C). To that, ELO (6 g) was added and stirred for about 30 minutes at about 140 °C (reaction temperature about 125 °C). The color of the reaction mixture changed into dark yellow. Additional ELO (44 g) was added to the reaction mixture and further heated at about 140 °C (reaction temperature about 125 °C) for about 25 minutes. A clear dark yellow solution was obtained as a prepolymer. The prepolymer was cooled to room temperature. Formation of solid was observed in the reaction mixture at room temperature. The reaction mixture was re-melted at about 140 °C and coated in a textile with a 100 pM bar coater. The coated textile was cured at about 200 °C in a pre-heated oven for about 2 h. The polymer formed a clean coating at the surface of the textile.

[0148] Example 1 (intermediate oligomer)

[0149] A mixture of Priamine™ 1071 (20 g) and Denacol GEX-521 (1 .292 g, 6.07 wt.-%) was stirred at room temperature for about 21 h. During stirring the brown mixture turned into less viscous liquid. The1H NMR of the reaction mixture showed a complete reaction of Denacol GEX-521 with Priamine™ 1071.

[0150] Viscosity of Example 1 was about 2,200 mPa s.

[0151] Example 2 (intermediate oligomer)

[0152] A mixture of Priamine™ 1071 (60 g) and Denacol GEX-521 (3.87 g, 6.07 wt.-%) was stirred at about 50 °C for about 4 h. The1H NMR of the reaction mixture showed a complete reaction of Denacol GEX-521 with Priamine™ 1071.

[0153] Example 3 (cured film via an intermediate oligomer)

[0154] 3.1 : A mixture of Example 2 (63.87 g) and epoxidized linseed oil (63.87 g) was heated at about 50 °C for about 17 h. The reaction mixture was further heated at about 80 °C for about 4 h. Then, it was allowed to cool to room temperature.

[0155] Viscosity of said reaction mixture was about 36,200 mPa s. 3.2: 2 g of said reaction mixture was taken in a silicon cup and cured at about 200 °C for about 2 h. A more flexible film was obtained when compared with Comparative Example 1 film, which is without Denacol GEX-521 (Table 1).

[0156] Example 4 (cured film via an intermediate oligomer)

[0157] 4.1 : A mixture of Priamine™ 1071 (10 g) and Denacol GEX-313 (0.7 g, 6.54 wt.-%) was stirred at room temperature for about 17 h. The1H NMR of the reaction mixture showed a complete reaction of Denacol GEX-313 with Priamine™ 1071 providing an intermediate oligomer having a viscosity of 2,155 m.Pas (measured at about 18 °C).

[0158] 4.2: 10.7 g of epoxidized linseed oil was added to the obtained intermediate oligomer of

[0159] Example 4.1 and mixed well at room temperature. 2 g of the reaction mixture were taken in a silicon cup and cured at about 200 °C for about 2 h. A flexible film having a very high tensile strength was obtained and the film strengths was improved when compared to the Example 3.2 film.

[0160] Example 5 (cured film via an intermediate oligomer)

[0161] 5.1 : A mixture of Priamine™ 1071 (40 g) and Denacol GEX-313 (2.6 g, 6.5 wt.-%) was stirred at room temperature for about 3 h. The1H NMR of the reaction mixture showed a complete reaction of Denacol GEX-313 with Priamine™ 1071 providing an intermediate oligomer.

[0162] 5.2: 4 g of epoxidized linseed oil and 6 g of the obtained intermediate oligomer of Example 5.1 were mixed to form a homogenous mixture. 2 g of the reaction mixture were taken in a silicon cup and cured at about 200 °C for about 2 h. A flexible film having a very high tensile strength was obtained. The film strength was improved when compared to the Example 3.2 film and the film tackiness was additionally improved when compared to the Example 4.2 film.

[0163] Table 1 : Summary of film properties; Tackiness was evaluated as 1 (very low), 2 (low), 3 (medium), 4 (high), and 5 (very high); Strength was evaluated as 1 (very high), 2 (high), 3 (medium), 4 (low), and 5 (very low); Flexibility was evaluated as 1 (very high), 2 (high), 3 (medium), 4 (low), and 5 (very low); and Elongation at break was evaluated as 1 (very high), 2 (high), 3 (medium), 4 (low), and 5 (very low).

[0164] Example 6 (coated textile)

[0165] 6.1 : A mixture of Priamine™ 1071 (25 g) and epoxidized linseed oil (25 g) was stirred at about 120 °C (reaction mixture temperature) for about 1 h. The1H NMR of the reaction mixture showed the formation of prepolymer.

[0166] 6.2: The prepolymer of 6.1 was coated in a textile with an about 100 pM bar coater. The coated textile was cured at about 200 °C in a pre-heated oven for about 2 h. The polymer formed a stable coating at the surface of the textile which improved hydrophobicity of textile surface.

[0167] The abrasion resistance of the coated textile according to Example 6.2 was higher than the abrasion resistance of the coated textile according to Compared Example 3.

[0168] 6.3: The prepolymer of 6.1 was coated in a cotton woven textile with an about 100 pM bar coater. The coated textile was cured at about 200 °C in a pre-heated oven for about 2 h. a) water resistance: As depicted in Figure 1 , water droplets remained on surface of material for more than 10 minutes, compared to less than 10 seconds in the untreated case (i.e. not treated cotton woven textile). b) flexible: Modified textile returned to original shape after being stretched or compressed, which was not the case for the untreated case. c) abrasion resistant: Surface felt more abrasion resistant, and appeared to be less subject to fibre pilling than in the untreated case. In general, films based on starting material comprising carboxylic acid groups provided less flexible films.

Claims

ClaimsA composition comprising at least one epoxidized vegetable oil (EVO) and ii) an intermediate oligomer (IO) comprising at least one primary amine group and at least one hydroxyl group.

2. The composition according to claim 1 .wherein the at least one epoxidized vegetable oil is selected from the group consisting of epoxidized rapeseed oil, epoxidized soybean oil, epoxidized linseed oil, epoxidized palm oil, epoxidized chia seed oil, and combinations thereof, preferably epoxidized linseed oil.

3. The composition according to claim 1 or 2, wherein the intermediate oligomer (IO) comprises a functionality selected from the group consisting of secondary amine, ether, (bivalent) carbocyclyl, (bivalent) heterocyclyl, and combinations thereof; and / or wherein the intermediate oligomer (IO) comprises a functionality having formula (A-1)(A-1), preferably having formula (A-2)(A-2); and / or wherein the intermediate oligomer (IO) has a viscosity of about 500 to about 6,000 mPa s, preferably of about 800 to about 5,000 mPa s, or of about 1 ,000 to about 4,000 mPa s, or of about1 .500 to about 3,500 mPa s, or of about 1 ,800 to about 3,000 mPa s, or of about 2,000 to about2.500 mPa s; and / or wherein the intermediate oligomer (IO) has a molecular weight of about 500 to about 20,000 g / mol, preferably of about 700 to about 15,000 g / mol, more preferably of about 900 to about 10,000 g / mol, or of about 1 ,000 to about 5,000 g / mol, or of about 3,000 to about 8,000 g / mol.

4. The composition according to any one of claim 1 to 3, wherein the intermediate oligomer (IO) is obtainable by a reaction of an epoxy compound (EC) comprising at least one, preferably at least two, terminal epoxy group, preferably wherein the epoxy compound (EC) comprises at least one ether functionality, more preferably wherein the epoxy compound (EC) is selected from the groupconsisting of , and combinations thereof, with an amine compound (AC) comprising at least one, preferably at least two, primary amine group, preferably wherein the amine compound (AC) comprises at least one functionality selected from the group consisting of (bivalent) carbocyclyl, (bivalent) heterocyclyl, secondary amine, and combinations thereof, wherein each carbon atom of the aforementioned (bivalent) carbocyclyl or (bivalent) heterocyclyl functionality is independently substituted or unsubstituted with RA, wherein RAis independently C1-C20-alkyl, C1-C20-alkoxy, or halogen, more preferably wherein the amine compound (AC) is derived from5. The composition according to claim 4, wherein the amine compound (AC) comprises from 4 to 50 carbon atoms, preferably from 10 to 45 carbon atoms, more preferably from 20 to 40 carbon atoms; and / or wherein the amine compound (AC) comprises two primary amine groups that are connected via 3 to 40, preferably via 4 to 30, more preferably via 5 to 20 adjacent carbon atoms; and / or wherein the amine compound (AC) comprises a functionality selected from the group consisting of bivalent heterocyclyl, bivalent aryl, bivalent saturated carbocyclyl, secondary amine, and combinations thereof, preferably selected from the group consisting of furanylene, phenylene, cyclohexylene, secondary amine, and combinations thereof, wherein each carbon atom of the aforementioned functionalities is independently substituted or unsubstituted with RA, wherein RAis independently C1 -C10-alkyl, C1-C10-alkoxy, or halogen; and / or wherein the amine compound (AC) comprises two primary amine group derived from a fatty acid dimer.

6. A method of preparing a composition comprising the step of a) mixing an epoxy compound (EC) comprising at least one terminal epoxy group with an amine compound (AC) comprising at least one primary amine group to provide an intermediate oligomer (IO) and b) mixing said intermediate oligomer (IO) with at least one epoxidized vegetable oil (EVO).

7. The method according to claim 6, wherein in step a), the amine compound (AC) is applied in excess over the epoxy compound (EC), preferably wherein the weight amount of the epoxy compound (EC) is of about 1 to about 20 wt.-%, preferably of about 2 to about 15 wt.-%, more preferably of about 3 to about 10 wt.-%, based on the combined weight of the amine compound (AC) and the epoxy compound (EC); and / or wherein in step a), the molar ratio of the amine groups to the epoxy groups is of about 1 :2 to about 20:1 , preferably of about 1 :1 to about 18:1 , more preferably of about 2:1 to about 16:1 , even more preferably of about 3:1 to about 14:1 , or of about 4:1 to about 13:1 , or of about 5:1 to about 12:1 , or of about 6:1 to about 11 :1 , or of about 7:1 to about 10:1 , or of about 8:1 to about 9:1 ; and / or wherein the at least one epoxidized vegetable oil (EVO) is selected from the group consisting of epoxidized rapeseed oil, epoxidized soybean oil, epoxidized linseed oil, epoxidized palm oil, epoxidized chia seed oil, and combinations thereof, preferably epoxidized linseed oil.

8. The method according to claim 6 or 7, wherein step a) is conducted at about 0 to about 100 °C, preferably at about 10 to about 80 °C, or at about 20 to about 60 °C, or at about 20 to about 40 °C, or at about 30 to about 60 °C; and / or wherein step a) is conducted for about 1 to about 40 hours, preferably for about 2 to about 30 hours, or for about 2 to about 10 hours, or for about 15 to about 26 hours.

9. The method according to any one of claims 6 to 8, wherein the epoxy compound (EC) comprises at least two terminal epoxy groups; and / or wherein the epoxy compound (EC) comprises at least one ether functionality; and / or wherein the epoxy compound (EC) comprises at least one hydroxyl group; and / orwherein the epoxy compound (EC) is selected from the group consisting of, and combinations thereof.

10. The method according to any one of claims 6 to 9, wherein the amine compound (AC) is at about 1 bar and at about 25 °C a liquid; and / or wherein the amine compound (AC) comprises at least two primary amine groups; and / or wherein the amine compound (AC) has a molecular weight of about 80 to about 2,000 g / mol, preferably of about 200 to about 1 ,500 g / mol, more preferably of about 300 to about 1 ,000 g / mol, or of about 400 to about 800 g / mol; and / or wherein the amine compound (AC) is11. A composition obtained by the method according to any one of claims 6 to 10.

12. A method for curing a composition, comprising i-1) providing the composition according to any one of claims 1 to 5 or 11 ; i-2) optionally heating the composition of step i-1) to a temperature of at least about 40 °C for at least about 5 minutes; and ii) curing the optionally heated composition at a temperature of at least about 50 °C.

13. The method according to claim 12, further comprising the steps of i-3) applying the optionally heated composition to a substrate; and ii) curing the substrate and the optionally heated composition of step i-3) to obtain a coated substrate.

14. The method according to claim 12 or 13, wherein step i-2) is conducted at a temperature of at least about 50 °C, preferably at a temperature of about 50 to about 200 °C, or of about 70 to about 100 °C or of about 100 to about 150 °C; and / or wherein step i-2) is conducted for at least about 30 minutes, preferably for at least about 60 minutes, more preferably for about 1 to about 10 hours or for about 1 to about 5 hours; and / or wherein step ii) is conducted at a temperature of at least about 100 °C, preferably at least about 130 °C, more preferably at a temperature of about 130 to about 300 °C, or of about 150 to about 250 °C; and / or wherein step ii) is conducted for at least about 30 minutes, preferably for at least about 60 minutes, more preferably for about 1 to about 5 hours.

15. The method according to claim 13 or 14, wherein the optionally heated composition is coated on the substrate with a thickness of about 10 to about 400 pm, preferably of about 30 to about 300 pm, more preferably of about 50 to about 200 pm; and / or wherein the substrate is a textile, preferably selected from the group consisting of cotton, linen, silk, wool, polyester, rayon, velour, leather and synthetic leather, preferably selected from the group consisting of cotton, leather and synthetic leather, more preferably selected from the group consisting of cotton, leather and synthetic leather.

16. Use of the composition according to any one of claims 1 to 5 or 11 to increase hydrophobicity of a substrate’s surface, preferably of a textile’s surface.

17. An adhesive comprising the composition according to any one of claims 1 to 5 or 11 .

18. Use of a mixture comprising at least one epoxidized vegetable oil (EVO) and at least one amine compound (AC) comprising at least two primary amine groups as a textile coating, preferably wherein the weight ratio of the at least one epoxidized vegetable oil (EVO) to the at least one amine compound (AC) is of about 20:1 to about 1 :20, preferably of about 10:1 to about 1 :10, more preferably of about 5:1 to about 1 :5, or of about 2:1 to about 1 :2.

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