Particles of (aziridinylhydroxy)-functionalized organic compounds

Abstract

The present invention relates to particles, which comprise a specific (aziridinylhydroxy)-functional organic component. The present invention also relates to mixtures comprising the particles. The present invention also relates to an aqueous dispersion comprising the particles. The present invention also relates to an aqueous composition comprising the particles. The present invention also relates to a coating composition comprising the particles. The present invention also relates to an aqueous coating composition comprising the particles. The present invention also relates to particles obtained by a method especially comprising the following steps: providing an aqueous dispersion comprising a specific (aziridinylhydroxy)-functional organic component. The present invention also relates to a parts kit, which comprises, in one of its parts, an aqueous dispersion containing a specific (aziridinylhydroxy)-functional organic component. The present invention also relates to cured forms of the various particles, mixtures, aqueous dispersions, aqueous compositions, coating compositions and aqueous coating compositions. The present invention also relates to articles, which comprise the particles and / or the mixtures, and / or the aqueous dispersions and / or aqueous compositions and / or the cured forms. The present invention also relates to various uses of the particles and / or the mixtures, and / or the aqueous dispersions and / or the aqueous compositions and / or the cured forms.

Description

[0001] The present invention relates to particles which comprise a specific (aziridinylhydroxy)-functional organic component. The present invention also relates to mixtures comprising said particles. The present invention also relates to aqueous dispersions comprising said particles. The present invention also relates to aqueous compositions comprising said particles. The present invention also relates to coating compositions comprising said particles. The present invention also relates to aqueous coating compositions comprising said particles. The present invention also relates to particles obtained by a method which especially comprises the step of providing an aqueous dispersion comprising a specific (aziridinylhydroxy)-functional organic component. The present invention also relates to a parts kit which comprises, in one of its parts, an aqueous dispersion containing a specific (aziridinylhydroxy)-functional organic component. The present invention also relates to cured forms of the various particles, mixtures, aqueous dispersions, aqueous compositions, coating compositions and aqueous coating compositions. The present invention also relates to articles which comprise said particles and / or said mixtures, and / or said aqueous dispersions and / or aqueous compositions and / or said cured forms. The present invention also relates to the various uses of said particles and / or said mixtures, and / or said aqueous dispersions and / or said aqueous compositions and / or said parts kit and / or said cured forms.

[0002] Several organic compounds bearing an aziridine ring (a 3-membered ring system consisting of one nitrogen atom and two carbon atoms) are known in the art. Aziridine - which is a three-membered cyclic amine (aziridine) - is an example of an organic compound bearing an aziridine ring. The ring strain associated with these molecules makes them highly reactive compounds and attractive for various industrial applications, such as as crosslinking agents in paint and coating compositions. However, so far, the use of organic compounds bearing an aziridine ring in paint and coating compositions has been by application of a solution of said compound in a volatile organic solvent, since said compounds are unstable in an aqueous environment. For example, trimethylolpropane tris(2-methyl-1-aziridinepropionate) (CAS number: 64265-57-2; available from DSM as 'Crosslinker CX-100') and pentaerythritol tris[3-(1-aziridinyl)propionate] (CAS number: 57116-45-7; available from Ichemco as ' Tris(2,3-dibromopropyl) phosphate (CAS No.: 126-72-7, available from LLC Aziridines as PZ-20), tris(aziridinyl) phosphine oxide (CAS No.: 545-55-1, available from LLC Aziridines as PZ-31), and pentaerythritol tris(3-(1-aziridinyl) propionate) (CAS No.: 57116-45-7, available from LLC Aziridines as PZ-33) are unstable in water; this instability of these three aziridine-ring-containing organic compounds in water is described in US-A-5133997. Thus, their use cannot be extended to aqueous paint and coating compositions. Given the global technological and regulatory trends towards safer, healthier, and more environmentally friendly paint and coating compositions, this instability in water is a significant drawback of aziridine-ring-containing organic compounds, with aqueous coating compositions being at the forefront of these trends. Unless a technical solution can enable aziridine-ring-containing organic compounds to be applied and used in an aqueous environment and at the same time maintain good crosslinking efficiency, these compounds will face the fate of disappearing from future industrial applications.

[0003] US2007 / 298006 A1 of Dendritic Nanotechnologies, PLLC (equivalent to WO 2006 / 115547A2) discloses dendrimers with enhanced amplification and internal functionality. Example 12 of US2007 / 298006 A1 discloses a compound with an aziridine ring. This compound is the only aziridine-ring-containing compound disclosed in US2007 / 298006 A1. The compound of Example 12 of US2007 / 298006 A1 was obtained as a clear colorless oil, had a molecular weight of 588 Da, and was used as a synthetic intermediate (through aziridine ring-opening reaction) in dendrimer preparation. US2007 / 298006 A1 neither discloses any particles—let alone any particles of aziridine-group-containing compounds, let alone these compounds having a molecular weight of at least 600 Da and at most 10,000 Da—nor discloses any composition containing said particles, such as an aqueous dispersion, the particles comprising an (aziridinyl hydroxy)-functional organic component. US2007 / 298006 A1 does not mention the combination of enhanced storage stability (at high temperatures and over an extended period; for 4 weeks at 50 °C) and maintenance of good, preferably very good, more preferably excellent crosslinking efficiency of an aqueous composition containing an aziridine-ring-containing organic compound, such as an aqueous dispersion.

[0004] EP 1865014 A1 of 3M Innovative Properties Company discloses a composition comprising a prepolymer as component (A), wherein the prepolymer comprises aziridinyl groups. On pages 8 - 14 (Compounds 1 to 10), EP 1865014 A1 discloses compounds with aziridine groups. However, these compounds - at least - do not have a hydroxyl group attached to a β - carbon atom connected to the nitrogen atom of the aziridine group. In addition, Compounds 1, 2, 3, 4, 9, 10 have an ester group attached to the above - mentioned β - carbon atom, while Compounds 5, 6, 7, 8 have a methyl group attached to the above - mentioned β - carbon atom. Thus, EP 1865014 A1 discloses very different compounds with aziridine groups. Therefore, EP 1865014 A1 not only discloses very different compounds with aziridine groups, but also does not disclose any particles - let alone any particles of compounds with aziridine groups, let alone that these compounds have a molecular weight of at least 600 Da and at most 10,000 Da - nor does it disclose any composition comprising such particles, such as an aqueous dispersion, wherein the particles comprise a (aziridinyl - hydroxy) - functional organic component. EP 1865014 A1 does not mention the combination of enhanced storage stability (at high temperature and for an extended period; 4 weeks at 50 °C) of an aqueous composition, such as an aqueous dispersion, comprising an organic compound with an aziridine ring and maintaining good, preferably very good, more preferably excellent cross - linking efficiency.

[0005] WO 2015 / 066868 A1 of 3M Innovative Properties Company discloses a fluoropolymer coating composition comprising an aqueous liquid medium, fluoropolymer particles dispersed in the aqueous liquid medium, and at least one aziridine compound. However, the aziridine compound - at least - does not have a hydroxyl group attached to a β - carbon atom connected to the nitrogen atom of the aziridine group. Thus, WO 2015 / 066868 A1 discloses very different compounds with aziridine groups. Therefore, WO 2015 / 066868 A1 not only discloses very different compounds with aziridine groups, but also does not disclose any particles of compounds with aziridine groups, let alone that these compounds have a molecular weight of at least 600 Da and at most 10,000 Da, nor does it disclose any composition comprising such particles, such as an aqueous dispersion, wherein the particles comprise a (aziridinyl - hydroxy) - functional organic component. WO 2015 / 066868 A1 does not mention the combination of enhanced storage stability (at high temperature and for an extended period; 4 weeks at 50 °C) of an aqueous composition, such as an aqueous dispersion, comprising an organic compound with an aziridine ring and maintaining good, preferably very good, more preferably excellent cross - linking efficiency.

[0006] US 3329674 of Thiokol Chemical Corporation discloses low molecular weight aziridinyl compounds. The molecular weights of these aziridinyl compounds are far lower than 600 Da (see Examples 1 to 7; the molecular weights of these compounds vary from 304 to 526). US 3329674 neither discloses any particles—let alone any particles of compounds with aziridinyl groups, let alone compounds having a molecular weight of at least 600 Da and at most 10,000 Da—nor does it disclose any composition containing such particles, such as an aqueous dispersion, the particles comprising an (aziridinylhydroxy)-functional organic component. US 3329674 does not mention the combination of enhanced storage stability (at high temperatures and over an extended period; for 4 weeks at 50 °C) of an aqueous composition, such as an aqueous dispersion, containing an organic compound with an aziridinyl ring and maintaining good, preferably very good, more preferably excellent crosslinking efficiency.

[0007] EP 0758662 A2 of Rockwell International Corporation discloses a curable resin system comprising an epoxy resin, a co-reactant selected from N-alkyl and N-aryl substituted aziridines, and a catalyst that promotes curing at ambient temperature. In Example 3 thereof, EP 0758662 A2 discloses the reaction of PY 306 epoxy resin with 2-methyl aziridine to provide an aziridine-terminated organic compound as a viscous liquid. According to EP 0758662 A2, PY 306 epoxy resin is a bisphenol F epoxy resin supplied by Ciba Geigy (see EP 0758662 A2, from cl.5, l.59 to cl.6, l.1). This aziridine-terminated organic compound is obtained as a viscous liquid and has a molecular weight of 426.25 Da (which is calculated based on the stoichiometry of the reactants disclosed in the first sentence of Example 3 of EP 0758662 A2), and it is used as a synthetic intermediate. EP 0758662 A2 neither discloses any particles—let alone any particles of compounds with aziridinyl groups, let alone compounds having a molecular weight of at least 600 Da and at most 10,000 Da—nor does it disclose any composition containing such particles, such as an aqueous dispersion, the particles comprising an (aziridinylhydroxy)-functional organic component. EP 0758662 A2 does not mention the combination of enhanced storage stability (at high temperatures and over an extended period; for 4 weeks at 50 °C) of an aqueous composition, such as an aqueous dispersion, containing an organic compound with an aziridinyl ring and maintaining good, preferably very good, more preferably excellent crosslinking efficiency.

[0008] Accordingly, there is a desire to employ an organic compound having an aziridine ring that exhibits enhanced storage stability over an extended period at elevated temperatures, such as 4 weeks at 50 °C, in an aqueous composition, such as an aqueous dispersion, an aqueous coating composition, and at the same time the organic compound having an aziridine ring employed in the aqueous environment maintains good, preferably very good, more preferably excellent crosslinking efficiency. In other words, there is a desire to employ an organic compound having an aziridine ring that exhibits enhanced storage stability over an extended period at elevated temperatures, such as 4 weeks at 50 °C, in an aqueous composition, such as an aqueous dispersion, an aqueous coating composition, and at the same time an aqueous composition, such as an aqueous dispersion, an aqueous coating composition, containing the organic compound having an aziridine ring maintains good, preferably very good, more preferably excellent crosslinking efficiency.

[0009] However, the above desire still represents an unmet need because solutions to problems involving highly reactive organic compounds, such as organic compounds having an aziridine ring, are particularly challenging.

[0010] Accordingly, an object of the present invention is to provide a solution to the above unmet need. In other words, an object of the present invention is to provide an aqueous composition, such as an aqueous dispersion, an aqueous coating composition, containing an organic compound having an aziridine ring, wherein the aqueous composition has enhanced storage stability at elevated temperatures over an extended period (4 weeks at 50 °C), and at the same time the organic compound having an aziridine ring employed in the aqueous environment maintains good, preferably very good, more preferably excellent crosslinking efficiency (crosslinking efficiency is defined and measured in the specification); or equivalently, an object of the present invention is to provide an aqueous composition, such as an aqueous dispersion, an aqueous coating composition, containing an organic compound having an aziridine ring, wherein the aqueous composition has enhanced storage stability at elevated temperatures over an extended period (4 weeks at 50 °C), and at the same time an aqueous composition containing the organic compound having an aziridine ring maintains good, preferably very good, more preferably excellent crosslinking efficiency (crosslinking efficiency is defined and measured in the specification).

[0011] This object is surprisingly achieved by using the particles as disclosed in the specification.

[0012] This object is surprisingly achieved by using the aqueous dispersion (containing the particles of the present invention) as disclosed in the specification.

[0013] More particularly, it has surprisingly been found that when the particles of the present invention are used in an aqueous dispersion, the latter has enhanced storage stability at elevated temperatures for an extended period of time (4 weeks at 50 °C), and at the same time the organic compounds with aziridine rings employed in said aqueous environment maintain good, preferably very good, more preferably excellent crosslinking efficiency (crosslinking efficiency is defined and determined in the specification); or equivalently, it has surprisingly been found that when the aqueous dispersion contains an organic compound with an aziridine ring in the form of fine particles, said aqueous composition has enhanced storage stability at elevated temperatures for an extended period of time (4 weeks at 50 °C), and at the same time the aqueous dispersion containing an organic compound with an aziridine ring in the form of fine particles maintains good, preferably very good, more preferably excellent crosslinking efficiency (crosslinking efficiency is defined and determined in the specification).

[0014] The aqueous dispersions (or generally aqueous compositions) of the present invention are also easy to use, and their aqueous nature results in good compatibility with aqueous adhesives and thus good mixing and low fouling during formulation. In addition, these compositions generally have viscosities that are easy to process, resulting in easy handling and accurate dosing.

[0015] The particles of the present invention may also have a series of further inventive uses, depending specifically on the manner and type of composition or method in which they can be used. Some of their additional uses are disclosed in the specification.

[0016] The particles of the present invention represent a significant technological advance in several industries that widely use particulate materials, powders or bulk solids, as they offer several inventive advantages over the prior art. Illustrative industries include, but are not limited to, food processing, pharmaceuticals, biotechnology, petrochemicals, mineral processing, metallurgy, detergents, power generation, paints, plastics, inks, and adhesives, 3D printing, household, toiletries and beauty industries. In addition, the aqueous dispersions of the present invention also represent a significant technological advance in several industries (especially paints, coatings, adhesives and inks) that require or are undergoing the use of highly reactive reagents such as compounds with aziridine rings. The reason is that the aqueous dispersions of the present invention provide these industries with a real opportunity not only to pursue new and innovative products and processes, but also to significantly improve the safety, health and environmental profile of their operations, products and processes; the reason is that the use of volatile organic solvents can be eliminated, and the aqueous dispersions of the present invention can be stored and transported easily and safely. At the same time, the aqueous dispersions of the present invention provide paint formulators with a large number of options to design and produce both 1K (one-component) and 2K (two-component) paint formulations, thereby increasing their freedom to formulate new and more environmentally friendly products. The initiation of 1K paint formulations is of great interest and represents a technological advance, as they are generally superior to 2K paint formulations.

[0017] Broadly, according to the present invention, there are provided particles as disclosed in the specification.

[0018] Broadly, according to the present invention, there are provided mixtures as disclosed in the specification.

[0019] Broadly, according to the present invention, there are provided aqueous dispersions as disclosed in the specification.

[0020] Broadly, according to the present invention, there are provided particles obtained by a method as disclosed in the specification.

[0021] Broadly, according to the present invention, there are provided aqueous compositions as disclosed in the specification.

[0022] Broadly, according to the present invention, there are provided kits of parts as disclosed in the specification.

[0023] Broadly, according to the present invention, there are provided cured forms as disclosed in the specification.

[0024] Broadly, according to the present invention, there are provided articles as disclosed in the specification.

[0025] Broadly, according to the present invention, there is provided the use of any one or any combination of the following as a crosslinking agent:

[0026] i) particles as disclosed in the specification;

[0027] ii) mixtures as disclosed in the specification;

[0028] iii) aqueous dispersions as disclosed in the specification;

[0029] iv) particles obtained by a method as disclosed in the specification;

[0030] v) aqueous compositions as disclosed in the specification.

[0031] Broadly, according to the present invention, there is provided the use of any one or any combination of the following in coatings, paints, inks, varnishes, lubricants, adhesives, additive manufacturing, 3D printing, textiles, waxes, fuels, photography, plastics, medical compositions, medical devices:

[0032] i) particles as disclosed in the specification;

[0033] ii) mixtures as disclosed in the specification;

[0034] iii) aqueous dispersions as disclosed in the specification;

[0035] iv) particles obtained by a method as disclosed in the specification;

[0036] v) An aqueous composition as disclosed in the specification

[0037] vi) A kit of parts as disclosed in the specification;

[0038] vii) A cured form as disclosed in the specification;

[0039] viii) An article as disclosed in the specification.

[0040] A1a Broadly, according to the present invention, there is provided a particle as disclosed in this specification.

[0041] The following paragraphs A1 to A55 constitute certain specific preferences of the particle according to A1a and certain further specific aspects of the invention of the particle according to A1a. More specifically, the preferences of the particle according to A1a include but are not limited to preferences A1 to A21, and the aspects of the invention of the particle according to A1a include but are not limited to aspects A22 to A55. Many other variations, combinations or embodiments of the present invention will be apparent to those skilled in the art, and these variations, combinations and embodiments are expected to be within the scope of the claimed invention. The antecedent basis of certain terms shown in the said preferences and the said aspects can be found in the preceding preferences or aspects. Any reference to a component includes its preferences and the preferred ranges disclosed throughout this specification.

[0042] Particles according to A1a or the disclosure from subsection 1 and any combination of the entire specification, wherein the particles - preferably organic particles - comprise an (aziridinylhydroxy)-functional organic component (AZ component), and wherein the particles have a size, as determined by dynamic light scattering according to the specification, of at least 2 nm and at most 3000 nm, preferably at least 2 nm and at most 2500 nm, more preferably at least 2 nm and at most 2000 nm, even more preferably at least 2 nm and at most 1500 nm, for example at least 2 nm and at most 1000 nm, for example at least 2 nm and at most 900 nm, for example at least 2 nm and at most 800 nm, for example at least 2 nm and at most 600 nm, for example at least 2 nm and at most 500 nm, for example at least 2 nm and at most 400 nm, for example at least 2 nm and at most 350 nm, for example at least 2 nm and at most 300 nm, for example at least 10 nm and at most 3000 nm, for example at least 10 nm and at most 2500 nm, for example at least 10 nm and at most 2000 nm, for example at least 10 nm and at most 1500 nm, for example at least 10 nm and at most 1000 nm, for example at least 10 nm and at most 900 nm, for example at least 10 nm and at most 800 nm, for example at least 10 nm and at most 600 nm, for example at least 10 nm and at most 500 nm, for example at least 10 nm and at most 400 nm, for example at least 10 nm and at most 350 nm, for example at least 10 nm and at most 300 nm, for example at least 20 nm and at most 3000 nm, for example at least 20 nm and at most 2500 nm, for example at least 20 nm and at most 2000 nm, for example at least 20 nm and at most 1500 nm, for example at least 20 nm and at most 1000 nm, for example at least 20 nm and at most 900 nm, for example at least 20 nm and at most 800 nm, for example at least 20 nm and at most 600 nm, for example at least 20 nm and at most 500 nm, for example at least 20 nm and at most 400 nm, for example at least 20 nm and at most 350 nm, for example at least 20 nm and at most 300 nm, for example at least 30 nm and at most 3000 nm, for example at least 30 nm and at most 2500 nm, for example at least 30 nm and at most 2000 nm, for example at least 30 nm and at most 1500 nm, for example at least 30 nm and at most 1000 nm, for example at least 30 nm and at most 900 nm, for example at least 30 nm and at most 800 nm, for example at least 30 nm and at most 600 nm, for example at least 30 nm and at most 500 nm, for example at least 30 nm and at most 400 nm, for example at least 30 nm and at most 350 nm, for example at least 30 nm and at most 300 nm, for example at least 40 nm and at most 3000 nm, for example at least 40 nm and at most 2500 nm, for example at least 40 nm and at most 2000 nm, for example at least 40 nm and at most 1500 nm,For example, at least 40 nm and at most 1000 nm, for example, at least 40 nm and at most 900 nm, for example, at least 40 nm and at most 800 nm, for example, at least 40 nm and at most 600 nm, for example, at least 40 nm and at most 500 nm, for example, at least 40 nm and at most 400 nm, for example, at least 40 nm and at most 350 nm, for example, at least 40 nm and at most 300 nm, for example, at least 50 nm and at most 3000 nm, for example, at least 50 nm and at most 2500 nm, for example, at least 50 nm and at most 2000 nm, for example, at least 50 nm and at most 1500 nm, for example, at least 50 nm and at most 1000 nm, for example, at least 50 nm and at most 900 nm, for example, at least 50 nm and at most 800 nm, for example, at least 50 nm and at most 600 nm, for example, at least 50 nm and at most 500 nm, for example, at least 50 nm and at most 400 nm, for example, at least 50 nm and at most 350 nm, for example, at least 50 nm and at most 300 nm, for example, at least 60 nm and at most 3000 nm, for example, at least 60 nm and at most 2500 nm, for example, at least 60 nm and at most 2000 nm, for example, at least 60 nm and at most 1500 nm, for example, at least 60 nm and at most 1000 nm, for example, at least 60 nm and at most 900 nm, for example, at least 60 nm and at most 800 nm, for example, at least 60 nm and at most 600 nm, for example, at least 60 nm and at most 500 nm, for example, at least 60 nm and at most 400 nm, for example, at least 60 nm and at most 350 nm, for example, at least 60 nm and at most 300 nm, for example, at least 70 nm and at most 3000 nm, for example, at least 70 nm and at most 2500 nm, for example, at least 70 nm and at most 2000 nm, for example, at least 70 nm and at most 1500 nm, for example, at least 70 nm and at most 1000 nm, for example, at least 70 nm and at most 900 nm, for example, at least 70 nm and at most 800 nm, for example, at least 70 nm and at most 600 nm, for example, at least 70 nm and at most 500 nm, for example, at least 70 nm and at most 400 nm, for example, at least 70 nm and at most 350 nm, for example, at least 70 nm and at most 300 nm, for example, at least 80 nm and at most 3000 nm, for example, at least 80 nm and at most 2500 nm, for example, at least 80 nm and at most 2000 nm, for example, at least 80 nm and at most 1500 nm, for example, at least 80 nm and at most 1000 nm, for example, at least 80 nm and at most 900 nm, for example, at least 80 nm and at most 800 nm, for example, at least 80 nm and at most 600 nm, for example, at least 80 nm and at most 500 nm, for example, at least 80 nm and at most 400 nm, for example, at least 80 nm and at most 350 nm, for example, at least 80 nm and at most 300 nm, for example, at least 90 nm and at most 3000 nm,For example, an average hydrodynamic diameter (D) based on scattering intensity of at least 90 nm and at most 2500 nm, such as at least 90 nm and at most 2000 nm, such as at least 90 nm and at most 1500 nm, such as at least 90 nm and at most 1000 nm, such as at least 90 nm and at most 900 nm, such as at least 90 nm and at most 800 nm, such as at least 90 nm and at most 600 nm, such as at least 90 nm and at most 500 nm, such as at least 90 nm and at most 400 nm, such as at least 90 nm and at most 350 nm, such as at least 90 nm and at most 300 nm, such as at least 100 nm and at most 3000 nm, such as at least 100 nm and at most 2500 nm, such as at least 100 nm and at most 2000 nm, such as at least 100 nm and at most 1500 nm, such as at least 100 nm and at most 1000 nm, such as at least 100 nm and at most 900 nm, such as at least 100 nm and at most 800 nm, such as at least 100 nm and at most 600 nm, such as at least 100 nm and at most 500 nm, such as at least 100 nm and at most 400 nm, such as at least 100 nm and at most 350 nm, such as at least 100 nm and at most 300 nm H )

[0043] and

[0044] wherein the (aziridinylhydroxy)-functional organic component (AZ component) is selected from the group consisting of the following i) to vi): i) an (aziridinylhydroxy)-functional organic compound AZ1 of formula A1 having only two aziridine rings (AZ1 compound); ii) an (aziridinylhydroxy)-functional organic compound AZ2 of formula A2 having only three aziridine rings (AZ2 compound); iii) an (aziridinylhydroxy)-functional organic compound AZ3 of formula A3 having only four aziridine rings (AZ3 compound); iv) an (aziridinylhydroxy)-functional organic compound AZ4 of formula A4 having only five aziridine rings (AZ4 compound); v) an (aziridinylhydroxy)-functional organic compound AZ5 of formula A5 having only six aziridine rings (AZ5 compound); and vi) mixtures thereof, preferably the AZ component is selected from the group consisting of the following i) to iv): i) an (aziridinylhydroxy)-functional organic compound AZ1 of formula A1 having only two aziridine rings (AZ1 compound); ii) an (aziridinylhydroxy)-functional organic composition AZ2 of formula A2 having only three aziridine rings (AZ2 compound); iii) an (aziridinylhydroxy)-functional organic compound AZ3 of formula A3 having only four aziridine rings (AZ3 compound); and iv) mixtures thereof

[0045]

[0046] wherein

[0047] X1 is a divalent aliphatic organic group or a divalent aromatic organic group, preferably X1 is a divalent aliphatic organic group;

[0048] X2 is a trivalent aliphatic organic group or a trivalent aromatic organic group, preferably X2 is a trivalent aliphatic organic group;

[0049] X3 is a tetravalent aliphatic organic group or a tetravalent aromatic organic group, preferably X3 is a tetravalent aliphatic organic group;

[0050] X4 is a pentavalent aliphatic organic group or a pentavalent aromatic organic group, preferably X4 is a pentavalent aliphatic organic group;

[0051] X5 is a hexavalent aliphatic organic group or a hexavalent aromatic organic group, preferably X5 is a hexavalent aliphatic organic group;

[0052] and wherein each of said X1 to X5 consists of a set of atoms covalently linked in a configuration comprising a straight-chain and / or branched-chain and / or cyclic structure, preferably consisting of a straight-chain and / or branched-chain and / or cyclic structure, said set of atoms being selected from the group consisting of the following i) to x): i) carbon and hydrogen atoms, ii) carbon, hydrogen and oxygen atoms, iii) carbon, hydrogen and nitrogen atoms, iv) carbon, hydrogen and sulfur atoms, v) carbon, hydrogen, oxygen and nitrogen atoms, vi) carbon, hydrogen, nitrogen and sulfur atoms, vii) carbon, hydrogen, oxygen and sulfur atoms, viii) carbon, hydrogen, oxygen, nitrogen and sulfur atoms, ix) carbon, hydrogen and silicon atoms, and x) carbon, hydrogen, oxygen and silicon atoms, and xi) any combination of ix) and / or x) with any one or all of iii) to viii),

[0053] and wherein each of said X1 to X5 has carbon atoms and hydrogen atoms,

[0054] and wherein each of said X1 to X5 optionally has oxygen atoms and / or nitrogen atoms and / or sulfur atoms and / or silicon atoms,

[0055] and wherein X1 and / or X2 and / or X3 and / or X4 and / or X5 may optionally contain ionic functional groups, preferably X1 and / or X2 and / or X3 and / or X4 and / or X5 do not contain ionic functional groups,

[0056] and wherein

[0057] Y is a monovalent organic group selected from the group consisting of: i) a monovalent (aziridinylhydroxyisopropyl) organic group of formula B1, ii) a monovalent (aziridinylhydroxycyclohexane) organic group of formula B2, and iii) a monovalent (aziridinylhydroxycyclohexane) organic group of formula B3, preferably Y is a monovalent (aziridinylhydroxyisopropyl) organic group of formula B1,

[0058]

[0059]

[0060] and wherein

[0061] R1 is selected from the group consisting of: hydrogen and methyl; and

[0062] R2 is selected from the group consisting of: hydrogen, methyl and C2-C5 alkyl; and

[0063] R3 is selected from the group consisting of: methyl and C2-C4 alkyl; and

[0064] R4 is selected from the group consisting of: hydrogen, methyl and C2-C4 alkyl;

[0065] and wherein

[0066] Y in each of the compounds A1 to A5 may be the same or different from each other, and wherein each of the single covalent bonds between said Y and each of X1 to X5 is selected from the group consisting of: carbon-carbon single bond, carbon-oxygen single bond and carbon-nitrogen single bond, preferably carbon-oxygen single bond and carbon-nitrogen single bond, more preferably carbon-oxygen single bond,

[0067] and wherein

[0068] Each of the compounds AZ1 to AZ5 has a molecular weight of at least 600 Da and at most 10,000 Da as determined by MALDI-TOF MS according to the specification.

[0069] A2 is a particle according to any one of A1a or A1 or any combination of the disclosure of subsection 1 and the entire specification, wherein the particle comprises at least 20% by weight, preferably at least 40% by weight, more preferably at least 55% by weight, even more preferably at least 70% by weight, such as at least 82% by weight, such as at least 85% by weight, such as at least 89% by weight, such as at least 93% by weight, such as at least 96% by weight, such as at least 99% by weight of the (aziridinylhydroxy)-functional organic component (AZ component).

[0070] Particles according to A1a or any one of A1 to A2 or any combination derived from the disclosure in subsection 1 and the entire specification, wherein each of the compounds AZ1 to AZ5 has a molecular weight of at least 600 Da and at most 8000 Da, preferably at least 600 Da and at most 7000 Da, more preferably at least 600 Da and at most 6000 Da, such as at least 600 Da and at most 5500 Da, such as at least 600 Da and at most 5000 Da, such as at least 600 Da and at most 4000 Da, such as at least 600 Da and at most 3500 Da, such as at least 600 Da and at most 3200 Da, such as at least 600 Da and at most 3000 Da, such as at least 600 Da and at most 2500 Da, such as at least 600 Da and at most 2200 Da, such as at least 600 Da and at most 2000 Da, such as at least 630 Da and at most 10000 Da, preferably at least 630 Da and at most 8000 Da, more preferably at least 630 Da and at most 7000 Da, even more preferably at least 630 Da and at most 6000 Da, such as at least 630 Da and at most 5500 Da, such as at least 630 Da and at most 5000 Da, such as at least 630 Da and at most 4000 Da, such as at least 630 Da and at most 3500 Da, such as at least 630 Da and at most 3200 Da, such as at least 630 Da and at most 3000 Da, such as at least 630 Da and at most 2500 Da, such as at least 630 Da and at most 2200 Da, such as at least 630 Da and at most 2000 Da, such as at least 640 Da and at most 10000 Da, such as at least 640 Da and at most 8000 Da, such as at least 640 Da and at most 7000 Da, such as at least 640 Da and at most 6000 Da, such as at least 640 Da and at most 5500 Da, such as at least 640 Da and at most 5000 Da, such as at least 640 Da and at most 4000 Da, such as at least 640 Da and at most 3500 Da, such as at least 640 Da and at most 3200 Da, such as at least 640 Da and at most 3000 Da, such as at least 640 Da and at most 2500 Da, such as at least 640 Da and at most 2200 Da, such as at least 640 Da and at most 2000 Da, such as at least 650 Da and at most 10000 Da, such as at least 650 Da and at most 8000 Da, such as at least 650 Da and at most 7000 Da, such as at least 650 Da and at most 6000 Da, such as at least 650 Da and at most 5500 Da, such as at least 650 Da and at most 5000 Da, such as at least 650 Da and at most 4000 Da, such as at least 650 Da and at most 3500 Da, such as at least 650 Da and at most 3200 Da, such as at least 650 Da and at most 3000 Da,For example, at least 650 Da and at most 2500 Da, such as at least 650 Da and at most 2200 Da, such as at least 650 Da and at most 2000 Da, such as at least 700 Da and at most 10000 Da, such as at least 700 Da and at most 8000 Da, such as at least 700 Da and at most 7000 Da, such as at least 700 Da and at most 6000 Da, such as at least 700 Da and at most 5500 Da, such as at least 700 Da and at most 5000 Da, such as at least 700 Da and at most 4000 Da, such as at least 700 Da and at most 3500 Da, such as at least 700 Da and at most 3200 Da, such as at least 700 Da and at most 3000 Da, such as at least 700 Da and at most 2500 Da, such as at least 700 Da and at most 2200 Da, such as at least 700 Da and at most 2000 Da, such as at least 750 Da and at most 10000 Da, such as at least 750 Da and at most 8000 Da, such as at least 750 Da and at most 7000 Da, such as at least 750 Da and at most 6000 Da, such as at least 750 Da and at most 5500 Da, such as at least 750 Da and at most 5000 Da, such as at least 750 Da and at most 4000 Da, such as at least 750 Da and at most 3500 Da, such as at least 750 Da and at most 3200 Da, such as at least 750 Da and at most 3000 Da, such as at least 750 Da and at most 2500 Da, such as at least 750 Da and at most 2200 Da, such as at least 750 Da and at most 2000 Da, such as at least 800 Da and at most 10000 Da, such as at least 800 Da and at most 8000 Da, such as at least 800 Da and at most 7000 Da, such as at least 800 Da and at most 6000 Da, such as at least 800 Da and at most 5500 Da, such as at least 800 Da and at most 5000 Da, such as at least 800 Da and at most 4000 Da, such as at least 800 Da and at most 3500 Da, such as at least 800 Da and at most 3200 Da, such as at least 800 Da and at most 3000 Da, such as at least 800 Da and at most 2500 Da, such as at least 800 Da and at most 2200 Da, such as at least 800 Da and at most 2000 Da, such as at least 850 Da and at most 10000 Da, such as at least 850 Da and at most 8000 Da, such as at least 850 Da and at most 7000 Da, such as at least 850 Da and at most 6000 Da, such as at least 850 Da and at most 5500 Da, such as at least 850 Da and at most 5000 Da, such as at least 850 Da and at most 4000 Da, such as at least 850 Da and at most 3500 Da, such as at least 850 Da and at most 3200 Da, such as at least 850 Da and at most 3000 DaFor example, at least 850 Da and at most 2500 Da, for example, at least 850 Da and at most 2200 Da, for example, at least 850 Da and at most 2000 Da, for example, at least 900 Da and at most 10000 Da, for example, at least 900 Da and at most 8000 Da, for example, at least 900 Da and at most 7000 Da, for example, at least 900 Da and at most 6000 Da, for example, at least 900 Da and at most 5500 Da, for example, at least 900 Da and at most 5000 Da, for example, at least 900 Da and at most 4000 Da, for example, at least 900 Da and at most 3500 Da, for example, at least 900 Da and at most 3200 Da, for example, at least 900 Da and at most 3000 Da, for example, at least 900 Da and at most 2500 Da, for example, at least 900 Da and at most 2200 Da, for example, at least 900 Da and at most 2000 Da, for example, at least 950 Da and at most 10000 Da, for example, at least 950 Da and at most 8000 Da, for example, at least 950 Da and at most 7000 Da, for example, at least 950 Da and at most 6000 Da, for example, at least 950 Da and at most 5500 Da, for example, at least 950 Da and at most 5000 Da, for example, at least 950 Da and at most 4000 Da, for example, at least 950 Da and at most 3500 Da, for example, at least 950 Da and at most 3200 Da, for example, at least 950 Da and at most 3000 Da, for example, at least 950 Da and at most 2500 Da, for example, at least 950 Da and at most 2200 Da, for example, at least 950 Da and at most 2000 Da, for example, at least 1000 Da and at most 10000 Da, for example, at least 1000 Da and at most 8000 Da, for example, at least 1000 Da and at most 7000 Da, for example, at least 1000 Da and at most 6000 Da, for example, at least 1000 Da and at most 5500 Da, for example, at least 1000 Da and at most 5000 Da, for example, at least 1000 Da and at most 4000 Da, for example, at least 1000 Da and at most 3500 Da, for example, at least 1000 Da and at most 3200 Da, for example, at least 1000 Da and at most 3000 Da, for example, at least 1000 Da and at most 2500 Da, for example, at least 1000 Da and at most 2200 Da, for example, at least 1000 Da and at most 2000 Da, for example, at least 1100 Da and at most 10000 Da, for example, at least 1100 Da and at most 8000 Da, for example, at least 1100 Da and at most 7000 Da, for example, at least 1100 Da and at most 6000 Da, for example, at least 1100 Da and at most 5500 Da, for example, at least 1100 Da and at most 5000 Da, for example, at least 1100 Da and at most 4000 Da, for example, at least 1100 Da and at most 3500 Da, for example, at least 1100 Da and at most 3200 DaA molecular weight of, for example, at least 1100 Da and at most 3000 Da, for example at least 1100 Da and at most 2500 Da, for example at least 1100 Da and at most 2200 Da, for example at least 1100 Da and at most 2000 Da, for example at least 1200 Da and at most 10000 Da, for example at least 1200 Da and at most 8000 Da, for example at least 1200 Da and at most 7000 Da, for example at least 1200 Da and at most 6000 Da, for example at least 1200 Da and at most 5500 Da, for example at least 1200 Da and at most 5000 Da, for example at least 1200 Da and at most 4000 Da, for example at least 1200 Da and at most 3500 Da, for example at least 1200 Da and at most 3200 Da, for example at least 1200 Da and at most 3000 Da, for example at least 1200 Da and at most 2500 Da, for example at least 1200 Da and at most 2200 Da, for example at least 1200 Da and at most 2000 Da.

[0071] A4. Particles according to any one of A1a or A1 to A3 or any combination of the disclosure from subsection 1 and the entire specification, wherein X1 is a divalent aliphatic organic group or a divalent aromatic organic group that is different from the divalent group of bisphenol A.

[0072] A5. Particles according to any one of A1a or A1 to A4 or any combination of the disclosure from subsection 1 and the entire specification, wherein X1 is a divalent aliphatic organic group or a divalent aromatic organic group that is different from the divalent organic groups selected from the group consisting of: the divalent group of bisphenol A, the divalent group of bisphenol AP, the divalent group of bisphenol AF, the divalent group of bisphenol B, the divalent group of bisphenol BP, the divalent group of bisphenol C, the divalent group of bisphenol C2, the divalent group of bisphenol E, the divalent group of bisphenol F, the divalent group of bisphenol G, the divalent group of bisphenol M, the divalent group of bisphenol S, the divalent group of bisphenol P, the divalent group of bisphenol PH, the divalent group of bisphenol TMC, the divalent group of bisphenol Z, the divalent group of dinitrobisphenol A, the divalent group of tetrabromobisphenol A, and combinations thereof; preferably X1 is a divalent aliphatic organic group.

[0073] Particles according to A1a or any one of A1 to A5 or any combination derived from the disclosure in Section 1 and the entire specification, wherein X1 and / or X2 and / or X3 and / or X4 and / or X5 comprise at least one structural unit or combination of structural units selected from the group consisting of: Unit 1, Unit 2, Unit 3, Unit 4, Unit 5, Unit 6, Unit 7, Unit 8, Unit 9, Unit 10, and Unit 11, preferably comprising at least one structural unit or combination of structural units selected from the group consisting of: Unit 1, Unit 4, Unit 9, Unit 10, and Unit 11, Units 1 to 11 are depicted below:

[0074]

[0075]

[0076] wherein

[0077] R' is selected from the group consisting of: hydrogen and methyl; and

[0078] j is an integer in the range from 1 to 5, preferably from 1 to 3; and

[0079] n is an integer ranging from and including 2 up to and including 50, preferably from and including 2 up to and including 40, more preferably from and including 2 up to and including 30, most preferably from and including 2 up to and including 20, such as from and including 2 up to and including 15, such as from and including 2 up to and including 10, such as from and including 2 up to and including 5 (e.g., n is 2), such as from and including 3 up to and including 50, such as from and including 3 up to and including 40, such as from and including 3 up to and including 30, such as from and including 3 up to and including 20, such as from and including 3 up to and including 15, such as from and including 3 up to and including 10, such as from and including 3 up to and including 5 (e.g., n is 3), such as from and including 4 up to and including 50, such as from and including 4 up to and including 40, such as from and including 4 up to and including 30, such as from and including 4 up to and including 20, such as from and including 4 up to and including 15, such as from and including 4 up to and including 10, such as from and including 4 up to and including 5 (e.g., n is 4), such as from and including 5 up to and including 50, such as from and including 5 up to and including 40, such as from and including 5 up to and including 30, such as from and including 5 up to and including 20, such as from and including 5 up to and including 15, such as from and including 5 up to and including 10 (e.g., n is 5), such as from and including 6 up to and including 50, such as from and including 6 up to and including 40, such as from and including 6 up to and including 30, such as from and including 6 up to and including 20, such as from and including 6 up to and including 15, such as from and including 6 up to and including 10 (e.g., n is 6), such as from and including 7 up to and including 50, such as from and including 7 up to and including 40, such as from and including 7 up to and including 30, such as from and including 7 up to and including 20, such as from and including 7 up to and including 15, such as from and including 7 up to and including 10 (e.g., n is 7), such as from and including 8 up to and including 50, such as from and including 8 up to and including 40, such as from and including 8 up to and including 30, such as from and including 8 up to and including 20, such as from and including 8 up to and including 15, such as from and including 8 up to and including 10 (e.g., n is 8), such as from and including 9 up to and including 50, such as from and including 9 up to and including 40, such as from and including 9 up to and including 30, such as from and including 9 up to and including 20, such as from and including 9 up to and including 15, such as from and including 9 up to and including 10 (e.g., n is 9), such as from and including 10 up to and including 50, such as from and including 10 up to and including 40, such as from and including 10 up to and including 30, such as from and including 10 up to and including 20, such as from and including 10 up to and including 15 (e.g., n is 10).

[0080] A7 Particles according to any one of A1a or A1 to A6 or any combination of the disclosure from subsection 1 and the entire specification, wherein

[0081] R1 is selected from the group consisting of: hydrogen and methyl; and

[0082] R2 is selected from the group consisting of: hydrogen, methyl and ethyl; and

[0083] R3 is selected from the group consisting of: methyl and C2-C4 alkyl; and

[0084] R4 is selected from the group consisting of: hydrogen, methyl and ethyl.

[0085] A8 A particle according to A1a or any one of A1 to A7 or any combination derived from the disclosure in subsection 1 and the entire specification, wherein the aggregation number of carbon atoms in R1, R2, R3 and R4 is at most 9, preferably at most 4, more preferably at most 2, for example at most 1.

[0086] A9 A particle according to A1a or any one of A1 to A8 or any combination derived from the disclosure in subsection 1 and the entire specification, wherein X1 and / or X2 and / or X3 and / or X4 and / or X5 do not contain one or any combination of the following structural units BP1, BP2, BP3 and BS

[0087]

[0088] A10 A particle according to A1a or any one of A1 to A9 or any combination derived from the disclosure in subsection 1 and the entire specification, wherein X1 and / or X2 and / or X3 and / or X4 and / or X5 contain at least one unit 11 as a structural unit.

[0089] A11 A particle according to A1a or any one of A1 to A10 or any combination derived from the disclosure in subsection 1 and the entire specification, wherein X1 is a divalent aliphatic organic group of formula A1a'

[0090]

[0091] wherein

[0092] R' is selected from the group consisting of: hydrogen and methyl; and

[0093] j is an integer in the range from 1 to 5, preferably from 1 to 3; and

[0094] n is an integer in the range from and including 2 up to and including 50, preferably from and including 2 up to and including 40, more preferably from and including 2 up to and including 30, most preferably from and including 2 up to and including 20, for example from and including 2 up to and including 15, for example from and including 2 up to and including 10, for example from and including 2 up to and including 5 (e.g., n is 2), for example from and including 3 up to and including 50, for example from and including 3 up to and including 40, for example from and including 3 up to and including 30, for example from and including 3 up to and including 20, for example from and including 3 up to and including 15, for example from and including 3 up to and including 10, for example from and including 3 up to and including 5 (e.g., n is 3), for example from and including 4 up to and including 50, for example from and including 4 up to and including 40, for example from and including 4 up to and including 30, for example from and including 4 up to and including 20, for example from and including 4 up to and including 15, for example from and including 4 up to and including 10, for example from and including 4 up to and including 5 (e.g., n is 4), for example from and including 5 up to and including 50, for example from and including 5 up to and including 40, for example from and including 5 up to and including 30, for example from and including 5 up to and including 20, for example from and including 5 up to and including 15, for example from and including 5 up to and including 10 (e.g., n is 5), for example from and including 6 up to and including 50, for example from and including 6 up to and including 40, for example from and including 6 up to and including 30, for example from and including 6 up to and including 20, for example from and including 6 up to and including 15, for example from and including 6 up to and including 10 (e.g., n is 6), for example from and including 7 up to and including 50, for example from and including 7 up to and including 40, for example from and including 7 up to and including 30, for example from and including 7 up to and including 20, for example from and including 7 up to and including 15, for example from and including 7 up to and including 10 (e.g., n is 7), for example from and including 8 up to and including 50, for example from and including 8 up to and including 40, for example from and including 8 up to and including 30, for example from and including 8 up to and including 20, for example from and including 8 up to and including 15, for example from and including 8 up to and including 10 (e.g., n is 8), for example from and including 9 up to and including 50, for example from and including 9 up to and including 40, for example from and including 9 up to and including 30, for example from and including 9 up to and including 20, for example from and including 9 up to and including 15, for example from and including 9 up to and including 10 (e.g., n is 9), for example from and including 10 up to and including 50, for example from and including 10 up to and including 40, for example from and including 10 up to and including 30, for example from and including 10 up to and including 20, for example from and including 10 up to and including 15 (e.g., n is 10).

[0095] Particles according to any one of A1a or A1 to A11 or a combination of the disclosure from subsection 1 and the entire specification, wherein each of X1 to X5 contains only single covalent bonds, or both single covalent bonds and double covalent bonds,

[0096] and wherein the single covalent bonds are selected from the group consisting of: carbon-carbon single bonds, carbon-hydrogen single bonds, carbon-nitrogen single bonds, carbon-sulfur single bonds, carbon-silicon single bonds, silicon-oxygen single bonds, nitrogen-hydrogen single bonds, sulfur-oxygen single bonds, carbon-oxygen single bonds where oxygen is bonded to hydrogen to form a hydroxyl group, silicon-oxygen-silicon single bonds,

[0097] and wherein the double covalent bonds are selected from the group consisting of: carbon-carbon double bonds, carbon-nitrogen double bonds, sulfur-oxygen double bonds, carbon-oxygen double bonds.

[0098] A13 Particles according to any one of A1a or A1 to A12 or a combination of the disclosure from subsection 1 and the entire specification, wherein each of X1 to X5 contains only single covalent bonds, or both single covalent bonds and double covalent bonds, and wherein the single covalent bonds are selected from the group consisting of: carbon-carbon single bonds, carbon-hydrogen single bonds, carbon-nitrogen single bonds, carbon-sulfur single bonds, carbon-silicon single bonds, silicon-oxygen single bonds, nitrogen-hydrogen single bonds, sulfur-oxygen single bonds, carbon-oxygen single bonds where oxygen is bonded to hydrogen to form a hydroxyl group, silicon-oxygen-silicon single bonds, and wherein the double covalent bonds are selected from the group consisting of: carbon-carbon double bonds, carbon-nitrogen double bonds, sulfur-oxygen double bonds, carbon-oxygen double bonds where carbon is a member of a ring structure, and carbon-oxygen double bonds where carbon is bonded to two other carbons through a carbon-carbon single bond, carbon-oxygen double bonds where carbon is bonded to another oxygen through a single bond and to nitrogen through a single bond, carbon-oxygen double bonds where carbon is bonded to two nitrogens through a carbon-nitrogen single bond, carbon-oxygen double bonds where carbon is bonded to two other oxygens through a single bond.

[0099] A14 Particles according to any one of A1a or A1 to A13 or a combination of the disclosure from subsection 1 and the entire specification, wherein, relative to the total number of atoms present in X1 and / or X2 and / or X3 and / or X4 and / or X5, the total number of carbon atoms and hydrogen atoms in X1 and / or X2 and / or X3 and / or X4 and / or X5 is at least 5%, preferably at least 10%, more preferably at least 15%, most preferably at least 20%, for example at least 25%, for example at least 30%, for example at least 35%, for example at least 40%, for example at least 45%, for example at least 50%, for example at least 55%, for example at least 60%, for example at least 65%, for example at least 70%, for example at least 75%, for example at least 80%, for example at least 85%, for example at least 90%, for example at least 95%, for example at least 97%, for example at least 98%, for example at least 99%, for example 100%.

[0100] Particles according to any one of A1a or A1 to A14 or any combination of the disclosure from Section 1 and the entire specification, wherein the aggregation number of all atoms present in X1 and / or X2 and / or X3 and / or X4 and / or X5 is at most 600, preferably at most 550, more preferably at most 500, most preferably at most 450, for example at most 400, for example at most 350, for example at most 300, for example at most 250, for example at most 200.

[0101] A16 Particles according to any one of A1a or A1 to A15 or any combination of the disclosure from Section 1 and the entire specification, wherein the AZ component is selected from the group consisting of the following i) to v): i) a (aziridinylhydroxy)-functional organic compound AZ1 of formula A1 (AZ1 compound), ii) a (aziridinylhydroxy)-functional organic compound AZ2 of formula A2 (AZ2 compound), iii) a (aziridinylhydroxy)-functional organic compound AZ3 of formula A3 (AZ3 compound), iv) a (aziridinylhydroxy)-functional organic compound AZ5 of formula A5 (AZ5 compound), and vi) mixtures thereof, and

[0102] wherein

[0103] the AZ1 compound is selected from the group consisting of: a compound having formula A1a and a compound having formula A1b, each of these formulas A1a - A1d being as described below

[0104]

[0105] wherein each n in formula A1a is independently selected and each n in formula A1a is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 10, more preferably from and including 2 up to and including 7, most preferably from and including 2 up to and including 5, for example from and including 2 up to and including 4, for example from and including 3 up to and including 20, for example from and including 3 up to and including 10, for example from and including 3 up to and including 7, for example from and including 3 up to and including 5, for example from and including 3 up to and including 4 (for example n equals 4); and

[0106]

[0107] wherein R in formula A1b is C3 - C 10a saturated alkylene group, and wherein each n in formula A1b is independently selected, and each n in formula A1a is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 10, more preferably from and including 2 up to and including 7, most preferably from and including 2 up to and including 5, such as from and including 2 up to and including 4, such as from and including 3 up to and including 20, such as from and including 3 up to and including 10, such as from and including 3 up to and including 7, such as from and including 3 up to and including 5, such as from and including 3 up to and including 4 (e.g., n equals 4); and

[0108]

[0109] wherein each n in formula A1c is independently selected, and each n in formula A1b is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 10, more preferably from and including 2 up to and including 7, most preferably from and including 2 up to and including 5, such as from and including 2 up to and including 4, such as from and including 3 up to and including 20, such as from and including 3 up to and including 10, such as from and including 3 up to and including 7, such as from and including 3 up to and including 5, such as from and including 3 up to and including 4 (e.g., n equals 4), and

[0110]

[0111] wherein R in formula A1d is C3-C 10 a saturated alkylene group, and wherein each n in formula A1d is independently selected, and each n in formula A1b is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 10, more preferably from and including 2 up to and including 7, most preferably from and including 2 up to and including 5, such as from and including 2 up to and including 4, such as from and including 3 up to and including 20, such as from and including 3 up to and including 10, such as from and including 3 up to and including 7, such as from and including 3 up to and including 5, such as from and including 3 up to and including 4 (e.g., n equals 4); and

[0112] wherein

[0113] the AZ2 compound is selected from the group consisting of: a compound having formula A2a, a compound having formula A2b, a compound having formula A2c, a compound having formula A2d, a compound having formula A2e, each of the formulas A2a - A2e being described below

[0114]

[0115] wherein n in formula A2a is an integer ranging from and including 2 up to and including 20, such as from and including 2 up to and including 10, such as from and including 2 up to and including 8, such as from and including 3 up to and including 20, such as from and including 3 up to and including 10, such as from and including 3 up to and including 8, such as from and including 4 up to and including 20, such as from and including 4 up to and including 10, such as from and including 4 up to and including 8, such as from and including 5 up to and including 20, such as from and including 5 up to and including 10, such as from and including 5 up to and including 8, such as from and including 6 up to and including 20, such as from and including 6 up to and including 10, such as from and including 6 up to and including 8 (e.g., n equals 7);

[0116] and

[0117]

[0118] wherein each n in formula A2b is independently selected, and each n in formula A2b is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 15, more preferably from and including 2 up to and including 12, most preferably from and including 2 up to and including 11, such as from and including 3 up to and including 20, such as from and including 3 up to and including 15, such as from and including 3 up to and including 12, such as from and including 3 up to and including 11, such as from and including 4 up to and including 20, such as from and including 4 up to and including 15, such as from and including 4 up to and including 12, such as from and including 4 up to and including 11, such as from and including 5 up to and including 20, such as from and including 5 up to and including 15, such as from and including 5 up to and including 12, such as from and including 5 up to and including 11, such as from and including 6 up to and including 20, such as from and including 6 up to and including 15, such as from and including 6 up to and including 12, such as from and including 6 up to and including 11, such as from and including 7 up to and including 20, such as from and including 7 up to and including 15, such as from and including 7 up to and including 12, such as from and including 7 up to and including 11, such as from and including 8 up to and including 20, such as from and including 8 up to and including 15, such as from and including 8 up to and including 12, such as from and including 8 up to and including 11, such as from and including 9 up to and including 20, such as from and including 9 up to and including 15, such as from and including 9 up to and including 12, such as from and including 9 up to and including 11, such as from and including 10 up to and including 20, such as from and including 10 up to and including 15, such as from and including 10 up to and including 12, such as from and including 10 up to and including 11 (e.g., n equals 11);

[0119] and

[0120]

[0121] Each n in formula A2c is independently selected, and each n in formula A2c is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 15, more preferably from and including 2 up to and including 12, most preferably from and including 2 up to and including 11, for example from and including 3 up to and including 20, for example from and including 3 up to and including 15, for example from and including 3 up to and including 12, for example from and including 3 up to and including 11, for example from and including 4 up to and including 20, for example from and including 4 up to and including 15, for example from and including 4 up to and including 12, for example from and including 4 up to and including 11, for example from and including 5 up to and including 20, for example from and including 5 up to and including 15, for example from and including 5 up to and including 12, for example from and including 5 up to and including 11, for example from and including 6 up to and including 20, for example from and including 6 up to and including 15, for example from and including 6 up to and including 12, for example from and including 6 up to and including 11, for example from and including 7 up to and including 20, for example from and including 7 up to and including 15, for example from and including 7 up to and including 12, for example from and including 7 up to and including 11, for example from and including 8 up to and including 20, for example from and including 8 up to and including 15, for example from and including 8 up to and including 12, for example from and including 8 up to and including 11, for example from and including 9 up to and including 20, for example from and including 9 up to and including 15, for example from and including 9 up to and including 12, for example from and including 9 up to and including 11, for example from and including 10 up to and including 20, for example from and including 10 up to and including 15, for example from and including 10 up to and including 12, for example from and including 10 up to and including 11 (e.g., n equals 11);

[0122] and

[0123]

[0124] and

[0125]

[0126] and

[0127] wherein

[0128] the AZ3 compound is selected from the group consisting of: a compound having formula A3a

[0129]

[0130] Each n in formula A3a is independently selected, and each n in formula A3a is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 15, more preferably from and including 2 up to and including 10, most preferably from and including 2 up to and including 9, for example from and including 2 up to and including 8, for example from and including 2 up to and including 7, for example from and including 2 up to and including 6, for example from and including 2 up to and including 5, for example from and including 2 up to and including 4, for example from and including 2 up to and including 3 (e.g., n equals 3, e.g., n equals 2);

[0131] and

[0132] wherein

[0133] the AZ5 compound is selected from the group consisting of: a compound having formula A5a

[0134]

[0135] Each n in formula A5a is independently selected, and each n in formula A5a is an integer ranging from and including 2 up to and including 40, preferably from and including 2 up to and including 30, more preferably from and including 2 up to and including 20, most preferably from and including 2 up to and including 10, for example from and including 2 up to and including 9, for example from and including 2 up to and including 8, for example from and including 2 up to and including 7, for example from and including 2 up to and including 6, for example from and including 2 up to and including 5, for example from and including 2 up to and including 4, for example from and including 3 up to and including 40, for example from and including 3 up to and including 30, for example from and including 3 up to and including 20, for example from and including 3 up to and including 10, for example from and including 3 up to and including 9, for example from and including 3 up to and including 8, for example from and including 3 up to and including 7, for example from and including 3 up to and including 6, for example from and including 3 up to and including 5, for example from and including 3 up to and including 4 (e.g., n equals 4, e.g., n equals 3).

[0136] A17 Particles according to any one of A1a or A1 to A16 or any combination derived from the disclosure of subsection 1 and the entire specification, wherein

[0137] X1 and / or X2 and / or X3 and / or X4 and / or X5 do not contain any structural units of phenol formaldehyde resin (also known as phenolic resin) (or equivalently derived therefrom); examples of phenol - aldehyde (PF) resins include novolac resins (acid - catalyzed PF resins with a formaldehyde to phenol ratio equal to or less than 1) and resole resins (alkali - catalyzed PF resins with a formaldehyde to phenol ratio greater than 1, typically equal to 1.5).

[0138] Particles according to A1a or any one of A1 to A17 or a combination of the disclosure from subsection 1 and the entire specification, wherein the AZ component is selected from the group consisting of: an AZ1 compound, and wherein the AZ1 compound is a compound of the following formula,

[0139]

[0140] Particles according to A1a or any one of A1 to A18 or a combination of the disclosure from subsection 1 and the entire specification, wherein

[0141] the AZ component is selected from the group consisting of: an AZ2 compound, and wherein the AZ2 compound is a compound of the following formula,

[0142]

[0143] Particles according to A1a or any one of A1 to A19 or a combination of the disclosure from subsection 1 and the entire specification, wherein

[0144] the AZ component is selected from the group consisting of: an AZ2 compound, and wherein the AZ2 compound is a compound of the following formula,

[0145]

[0146] Particles according to A1a or any one of A1 to A20 or a combination of the disclosure from subsection 1 and the entire specification, wherein the AZ component is selected from the group consisting of: an AZ2 compound, and wherein the AZ2 compound is a compound of the following formula,

[0147]

[0148] A mixture according to a combination of the disclosure from subsection 1 and subsection 3 and the entire specification, the mixture comprising:

[0149] i) Particles of an (aziridinylhydroxy)-functional organic component according to A1a or any one of A1 to A21 or a combination of the disclosure from subsection 1 and subsection 3 and the entire specification, and

[0150] ii) a polymer having an acid value, determined according to ASTM D1639-90(1996)e1, of at least 5 mg KOH / g and at most 300 mg KOH / g, preferably at least 8 mg KOH / g and at most 200 mg KOH / g, more preferably at least 10 mg KOH / g and at most 150 mg KOH / g, and wherein the polymer may optionally contain ionic functional groups.

[0151] A23 A mixture according to 22 or derived from the disclosure of Subsection 1 and Subsection 3 and any combination of the entire specification, wherein the polymer is selected from the group consisting of: polyester, polyamide, polycarbonate, polyimide, alkyd resin, urethane-modified alkyd resin (uralkyds), polyacrylics, polyurethane, poly(urethane-acrylics), and mixtures thereof, preferably the polymer is selected from the group consisting of: polyamide, polyacrylics, polyurethane, poly(urethane-acrylics), and mixtures thereof, most preferably the polymer is selected from the group consisting of: polyacrylics, polyurethane, poly(urethane-acrylics), and mixtures thereof.

[0152] A24 A mixture according to any one of A22 to A23 or derived from the disclosure of Subsection 1 and Subsection 3 and any combination of the entire specification, wherein the particles are present in an amount of at least 10% by weight and at most 100% by weight, preferably at least 15% by weight and at most 95% by weight, more preferably at least 20% by weight and at most 90% by weight, such as at least 25% by weight and at most 85% by weight, such as at least 30% by weight and at most 80% by weight, such as at least 35% by weight and at most 75% by weight, such as at least 40% by weight and at most 70% by weight, such as at least 40% by weight and at most 65% by weight, such as at least 40% by weight and at most 60% by weight, and wherein the total amount of all components constituting the mixture totals 100% by weight.

[0153] A25 A mixture according to any one of A22 to A24 or derived from the disclosure of Subsection 1 and Subsection 3 and any combination of the entire specification, wherein the polymer is present in an amount of at least 5% by weight and at most 65% by weight, preferably at least 10% by weight and at most 60% by weight, more preferably at least 20% by weight and at most 55% by weight, such as at least 30% by weight and at most 50% by weight, based on the total weight of the aqueous composition, and wherein the total amount of all components constituting the mixture totals 100% by weight.

[0154] A26 An aqueous dispersion according to the disclosure from subsection 3 and subsection 1 and any combination of the entire specification, the aqueous dispersion having a pH of at least 7.5 and at most 14.0, preferably at least 8.0 and at most 14.0, such as at least 8.5 and at most 13.5, such as at least 9.0 and at most 13.0, such as at least 9.2 and at most 12.5, such as at least 9.4 and at most 12.0, such as at least 9.6 and at most 11.6, such as at least 10.5 and at most 11.5, as determined according to ISO 976:2013 and according to the specification, and wherein the aqueous dispersion comprises:

[0155] i) water, and

[0156] ii) particles according to any one of A1a or A1 to A21 or according to the disclosure from subsection 1 and subsection 3 and any combination of the entire specification, the particles being dispersed in the water.

[0157] A27 An aqueous dispersion according to A26 or according to the disclosure from subsection 3 and subsection 1 and any combination of the entire specification, wherein, based on the total weight of the aqueous dispersion, the water is present in an amount of at least 30% by weight and at most 95% by weight, preferably at least 45% by weight and at most 85% by weight, such as at least 50% by weight and at most 70% by weight, such as at least 55% by weight and at most 65% by weight, and wherein the total amount of all components constituting the aqueous dispersion totals 100% by weight.

[0158] A28 An aqueous dispersion according to any one of A26 - A27 or according to the disclosure from subsection 3 and subsection 1 and any combination of the entire specification, the aqueous dispersion further comprising, based on the total weight of the aqueous dispersion, an amount of at most 40% by weight, preferably at most 30% by weight, such as at most 25% by weight, such as at most 20% by weight, such as at most 12% by weight, such as at most 10% by weight, such as at most 8% by weight, such as at most 5% by weight, such as at most 4% by weight, such as at most 3% by weight, such as at most 2% by weight, such as at most 1% by weight, such as at most 0.5% by weight, such as at most 0.2% by weight, such as at most 0.1% by weight of an organic solvent.

[0159] A29 An aqueous dispersion according to any one of A26 - A28 or according to the disclosure from subsection 3 and subsection 1 and any combination of the entire specification, wherein the aqueous dispersion does not contain an organic solvent.

[0160] An aqueous dispersion according to any one of A26 - A29 or a combination of the disclosure from Subsection 3 and Subsection 1 and the entire specification, wherein based on the total weight of the aqueous dispersion, the particles are present in an amount of at least 5 wt% and at most 70 wt%, preferably at least 10 wt% and at most 60 wt%, more preferably at least 20 wt% and at most 55 wt%, such as at least 25 wt% and at most 55 wt%, such as at least 30 wt% and at most 55 wt%, such as at least 35 wt% and at most 55 wt%, such as at least 35 wt% and at most 50 wt%, such as at least 35 wt% and at most 45 wt%, and wherein the total amount of all components constituting the aqueous dispersion totals 100 wt%.

[0161] An aqueous dispersion according to any one of A26 - A30 or a combination of the disclosure from Subsection 3 and Subsection 1 and the entire specification, wherein the aqueous dispersion comprises a component T selected from the group consisting of: i) an organic compound having a molecular weight of less than 600 Da as determined by MALDI - TOF MS according to the specification and comprising at least one aziridine ring, and ii) mixtures thereof, and based on the total weight of the AZ compound, the amount of the component T as determined by LC - MS according to the specification is at most 5 wt%, preferably at most 4 wt%, more preferably at most 3 wt%, such as at most 2 wt%, such as at most 1 wt%, such as at most 0.5 wt%, such as at most 0.1 wt%, such as at most 0.05 wt%.

[0162] An aqueous dispersion according to any one of A26 - 31 or a combination of the disclosure from Subsection 3 and Subsection 1 and the entire specification, wherein the aqueous dispersion does not contain the component T.

[0163] An aqueous dispersion according to any one of A26 - A32 or a combination of the disclosure from Subsection 3 and Subsection 1 and the entire specification, wherein based on the total weight of the aqueous dispersion, the amount of chloride determined according to ASTM D1726 - 11(2019) is at most 0.3 wt%, preferably at most 0.2 wt%, more preferably at most 0.1 wt%, such as at most 0.05 wt%, such as at most 0.03 wt%.

[0164] An aqueous dispersion according to any one of A26 - A33 or a combination of the disclosure from Subsection 3 and Subsection 1 and the entire specification, wherein the aqueous dispersion is an aqueous coating dispersion.

[0165] Particles obtained by a method comprising the following steps:

[0166] i) providing an aqueous dispersion according to any one of A26 - A34 or a combination of the disclosure from Subsection 3 and Subsection 1 and the entire specification; and

[0167] ii) removing the water and any organic solvent if present from the aqueous dispersion, preferably by spray drying or freeze drying or distillation under vacuum, to obtain the particles; and

[0168] iii) collecting the particles, and

[0169] iv) optionally further drying the particles; and

[0170] v) optionally applying means, such as grinding, which convert the collected particles into any form in which the solid material may exist under standard conditions.

[0171] A36 Particles according to A35 or any combination derived from the disclosure in Section 3 and Section 1 and the entire specification, wherein the particles have a size as determined by dynamic light scattering according to the specification of at least 2 nm and at most 3000 nm, preferably at least 2 nm and at most 2500 nm, more preferably at least 2 nm and at most 2000 nm, even more preferably at least 2 nm and at most 1500 nm, for example at least 2 nm and at most 1000 nm, for example at least 2 nm and at most 900 nm, for example at least 2 nm and at most 800 nm, for example at least 2 nm and at most 600 nm, for example at least 2 nm and at most 500 nm, for example at least 2 nm and at most 400 nm, for example at least 2 nm and at most 350 nm, for example at least 2 nm and at most 300 nm, for example at least 10 nm and at most 3000 nm, for example at least 10 nm and at most 2500 nm, for example at least 10 nm and at most 2000 nm, for example at least 10 nm and at most 1500 nm, for example at least 10 nm and at most 1000 nm, for example at least 10 nm and at most 900 nm, for example at least 10 nm and at most 800 nm, for example at least 10 nm and at most 600 nm, for example at least 10 nm and at most 500 nm, for example at least 10 nm and at most 400 nm, for example at least 10 nm and at most 350 nm, for example at least 10 nm and at most 300 nm, for example at least 20 nm and at most 3000 nm, for example at least 20 nm and at most 2500 nm, for example at least 20 nm and at most 2000 nm, for example at least 20 nm and at most 1500 nm, for example at least 20 nm and at most 1000 nm, for example at least 20 nm and at most 900 nm, for example at least 20 nm and at most 800 nm, for example at least 20 nm and at most 600 nm, for example at least 20 nm and at most 500 nm, for example at least 20 nm and at most 400 nm, for example at least 20 nm and at most 350 nm, for example at least 20 nm and at most 300 nm, for example at least 30 nm and at most 3000 nm, for example at least 30 nm and at most 2500 nm, for example at least 30 nm and at most 2000 nm, for example at least 30 nm and at most 1500 nm, for example at least 30 nm and at most 1000 nm, for example at least 30 nm and at most 900 nm, for example at least 30 nm and at most 800 nm, for example at least 30 nm and at most 600 nm, for example at least 30 nm and at most 500 nm, for example at least 30 nm and at most 400 nm, for example at least 30 nm and at most 350 nm, for example at least 30 nm and at most 300 nm, for example at least 40 nm and at most 3000 nm, for example at least 40 nm and at most 2500 nm, for example at least 40 nm and at most 2000 nm, for example at least 40 nm and at most 1500 nm, for example at least 40 nm and at most 1000 nm, for example at least 40 nm and at most 900 nm,For example, at least 40 nm and at most 800 nm, for example, at least 40 nm and at most 600 nm, for example, at least 40 nm and at most 500 nm, for example, at least 40 nm and at most 400 nm, for example, at least 40 nm and at most 350 nm, for example, at least 40 nm and at most 300 nm, for example, at least 50 nm and at most 3000 nm, for example, at least 50 nm and at most 2500 nm, for example, at least 50 nm and at most 2000 nm, for example, at least 50 nm and at most 1500 nm, for example, at least 50 nm and at most 1000 nm, for example, at least 50 nm and at most 900 nm, for example, at least 50 nm and at most 800 nm, for example, at least 50 nm and at most 600 nm, for example, at least 50 nm and at most 500 nm, for example, at least 50 nm and at most 400 nm, for example, at least 50 nm and at most 350 nm, for example, at least 50 nm and at most 300 nm, for example, at least 60 nm and at most 3000 nm, for example, at least 60 nm and at most 2500 nm, for example, at least 60 nm and at most 2000 nm, for example, at least 60 nm and at most 1500 nm, for example, at least 60 nm and at most 1000 nm, for example, at least 60 nm and at most 900 nm, for example, at least 60 nm and at most 800 nm, for example, at least 60 nm and at most 600 nm, for example, at least 60 nm and at most 500 nm, for example, at least 60 nm and at most 400 nm, for example, at least 60 nm and at most 350 nm, for example, at least 60 nm and at most 300 nm, for example, at least 70 nm and at most 3000 nm, for example, at least 70 nm and at most 2500 nm, for example, at least 70 nm and at most 2000 nm, for example, at least 70 nm and at most 1500 nm, for example, at least 70 nm and at most 1000 nm, for example, at least 70 nm and at most 900 nm, for example, at least 70 nm and at most 800 nm, for example, at least 70 nm and at most 600 nm, for example, at least 70 nm and at most 500 nm, for example, at least 70 nm and at most 400 nm, for example, at least 70 nm and at most 350 nm, for example, at least 70 nm and at most 300 nm, for example, at least 80 nm and at most 3000 nm, for example, at least 80 nm and at most 2500 nm, for example, at least 80 nm and at most 2000 nm, for example, at least 80 nm and at most 1500 nm, for example, at least 80 nm and at most 1000 nm, for example, at least 80 nm and at most 900 nm, for example, at least 80 nm and at most 800 nm, for example, at least 80 nm and at most 600 nm, for example, at least 80 nm and at most 500 nm, for example, at least 80 nm and at most 400 nm, for example, at least 80 nm and at most 350 nm, for example, at least 80 nm and at most 300 nm, for example, at least 90 nm and at most 3000 nm, for example, at least 90 nm and at most 2500 nm, for example, at least 90 nm and at most 2000 nmFor example, an average hydrodynamic diameter (D) based on scattering intensity of at least 90 nm and at most 1500 nm, such as at least 90 nm and at most 1000 nm, such as at least 90 nm and at most 900 nm, such as at least 90 nm and at most 800 nm, such as at least 90 nm and at most 600 nm, such as at least 90 nm and at most 500 nm, such as at least 90 nm and at most 400 nm, such as at least 90 nm and at most 350 nm, such as at least 90 nm and at most 300 nm, such as at least 100 nm and at most 3000 nm, such as at least 100 nm and at most 2500 nm, such as at least 100 nm and at most 2000 nm, such as at least 100 nm and at most 1500 nm, such as at least 100 nm and at most 1000 nm, such as at least 100 nm and at most 900 nm, such as at least 100 nm and at most 800 nm, such as at least 100 nm and at most 600 nm, such as at least 100 nm and at most 500 nm, such as at least 100 nm and at most 400 nm, such as at least 100 nm and at most 350 nm, such as at least 100 nm and at most 300 nm H )。

[0172] A37 An aqueous composition according to the disclosure of subsection 3 and subsection 1 and any combination of the entire specification, the aqueous composition comprising:

[0173] i) An aqueous dispersion according to any one of A26 to A34 or any combination of the disclosure of subsection 3 and subsection 1, and

[0174] ii) A polymer having an acid value in the range of 5 mg KOH / g to 300 mg KOH / g, preferably 8 mg KOH / g to 200 mg KOH / g, more preferably 10 mg KOH / g to 150 mg KOH / g, as determined according to ASTM D1639-90(1996)e1, and wherein the polymer may optionally comprise ionic functional groups.

[0175] A38 An aqueous composition according to A37 or any combination of the disclosure of subsection 3 and subsection 1 and the entire specification, wherein the aqueous composition has a pH of at least 7.5 and at most 14.0, preferably at least 8.0 and at most 14.0, such as at least 8.5 and at most 13.5, such as at least 9.0 and at most 13.0, such as at least 9.2 and at most 12.5, such as at least 9.4 and at most 12.0, such as at least 9.6 and at most 11.6, as determined according to ISO 976:2013 and according to the specification.

[0176] An aqueous composition according to any one of A37 - A38 or any combination derived from the disclosure in Section 3 and Section 1 and the entire specification, wherein the polymer is selected from the group consisting of: polyester, polyamide, polycarbonate, polyimide, alkyd resin, urethane-modified alkyd resin (uralkyds), polyacrylate, polyurethane, poly(urethane-acrylate), and mixtures thereof, preferably the polymer is selected from the group consisting of: polyamide, polyacrylate, polyurethane, poly(urethane-acrylate), and mixtures thereof, most preferably the polymer is selected from the group consisting of: polyacrylate, polyurethane, poly(urethane-acrylate), and mixtures thereof.

[0177] An aqueous composition according to any one of A37 - A39 or any combination derived from the disclosure in Section 3 and Section 1 and the entire specification, the aqueous composition further comprising, based on the total weight of the aqueous composition, an amount of up to 35 wt%, preferably up to 30 wt%, such as up to 25 wt%, such as up to 20 wt%, such as up to 15 wt%, such as up to 12 wt%, such as up to 10 wt%, such as up to 8 wt%, such as up to 5 wt%, such as up to 4 wt%, such as up to 3 wt%, such as up to 2 wt%, such as up to 1 wt%, such as up to 0.5 wt%, such as up to 0.2 wt%, such as up to 0.1 wt% of an organic solvent.

[0178] An aqueous composition according to any one of A37 - A40 or any combination derived from the disclosure in Section 3 and Section 1 and the entire specification, wherein the aqueous dispersion is present in the aqueous composition in an amount of at least 0.1 wt% and at most 50 wt%, preferably at least 0.2 wt% and at most 45 wt%, more preferably at least 0.3 wt% and at most 40 wt%, such as at least 0.4 wt% and at most 35 wt%, such as at least 0.5 wt% and at most 30 wt%, such as at least 0.6 wt% and at most 25 wt%, such as at least 0.7 wt% and at most 20 wt%, such as at least 0.8 wt% and at most 15 wt%, such as at least 0.9 wt% and at most 12 wt%, such as at least 1 wt% and at most 10 wt%, such as at least 1.2 wt% and at most 8 wt%, such as at least 0.3 wt% and at most 25 wt%, such as at least 0.8 wt% and at most 15 wt%, such as at least 1.5 wt% and at most 12 wt%, such as at least 2.5 wt% and at most 10 wt%, such as at least 3 wt% and at most 8 wt%, and wherein the total amount of all components constituting the aqueous composition totals 100 wt%.

[0179] An aqueous composition according to any one of A37 - A41 or a combination of the disclosure from Subsection 3 and Subsection 1 and the entire specification, wherein the polymer is present in the aqueous composition in an amount of at least 5% by weight and at most 65% by weight, preferably at least 10% by weight and at most 60% by weight, more preferably at least 20% by weight and at most 55% by weight, such as at least 30% by weight and at most 50% by weight, based on the total weight of the aqueous composition, and wherein the total amount of all components constituting the aqueous composition totals 100% by weight.

[0180] An aqueous composition according to any one of A37 - A42 or a combination of the disclosure from Subsection 3 and Subsection 1 and the entire specification, wherein the aqueous composition does not contain an organic solvent.

[0181] An aqueous composition according to any one of A37 - A43 or a combination of the disclosure from Subsection 3 and Subsection 1 and the entire specification, wherein the aqueous composition is a coating composition, preferably an aqueous coating composition.

[0182] A kit of parts according to a combination of the disclosure from Subsection 4, Subsection 3, and Subsection 1 and the entire specification, the kit of parts comprising parts A and B physically separated from each other, wherein:

[0183] i) Part A contains an aqueous dispersion according to any one of A26 - A34 or a combination of the disclosure from Subsection 3 and Subsection 1 and the entire specification; and

[0184] ii) Part B contains a polymer having an acid value in the range of 5 mg KOH / g to 300 mg KOH / g, preferably 8 mg KOH / g to 200 mg KOH / g, more preferably 10 mg KOH / g to 150 mg KOH / g as determined according to ASTM D1639 - 90(1996)e1, and wherein the polymer may optionally contain ionic functional groups, and wherein the polymer is preferably selected from the group consisting of: polyester, polyamide, polycarbonate, polyimide, alkyd resin, urethane - modified alkyd resin (uralkyds), polyacrylate, polyurethane, poly(urethane - acrylate), and mixtures thereof, more preferably the polymer is selected from the group consisting of: polyamide, polyacrylate, polyurethane, poly(urethane - acrylate), and mixtures thereof, most preferably the polymer is selected from the group consisting of: polyacrylate, polyurethane, poly(urethane - acrylate), and mixtures thereof,

[0185] Wherein the part A does not contain the polymer of the part B, and the part B does not contain the aqueous dispersion of the part A.

[0186] A46 The cured form of particles according to any one of A1a or A1 - A21 or any combination of the disclosure from Section 4, Section 3, and Section 1 and the entire specification.

[0187] A47 The cured form of a mixture according to any one of A22 - A25 or any combination of the disclosure from Section 4, Section 3, and Section 1 and the entire specification.

[0188] A48 The cured form of an aqueous dispersion according to any one of A26 - A34 or any combination of the disclosure from Section 4, Section 3, and Section 1 and the entire specification.

[0189] A49 The cured form of particles according to any one of A35 - A36 or any combination of the disclosure from Section 4, Section 3, and Section 1 and the entire specification.

[0190] A50 The cured form of an aqueous composition according to any one of A37 - A45 or any combination of the disclosure from Section 4, Section 3, and Section 1 and the entire specification.

[0191] A51 The cured form according to any one of A46 - A50 or any combination of the disclosure from Section 4, Section 3, and Section 1 and the entire specification, wherein the cured form is a film.

[0192] A52 An article, the article comprising: i) particles according to any one of A1a and A1 - A21 or any combination of the disclosure from Section 4, Section 3, and Section 1 and the entire specification; and / or ii) a mixture according to any one of A22 to A25 or any combination of the disclosure from Section 4, Section 3, and Section 1 and the entire specification; and / or iii) an aqueous dispersion according to any one of A26 to A34 or any combination of the disclosure from Section 4, Section 3, and Section 1 and the entire specification; and / or iv) particles according to any one of A35 - A36 or any combination of the disclosure from Section 4, Section 3, and Section 1 and the entire specification; and / or v) an aqueous composition according to any one of A37 - A45 or any combination of the disclosure from Section 4, Section 3, and Section 1 and the entire specification; and / or vi) a cured form according to any one of A46 - A51 or the disclosure from Section 4, Section 3, and Section 1 and the entire specification.

[0193] An article according to A52 or the disclosure from Sections 4, 3, and 1 and any combination of the entire specification, wherein the article is selected from the group consisting of: textiles, glass, metal, composites, plastics, wood, engineered wood, wood imitation, leather, artificial leather, paper, fibers.

[0194] Use of any one or any combination of the following as a crosslinking agent:

[0195] i) Particles according to A1a and any one of A1 - A21 or the disclosure from Sections 4, 3, and 1 and any combination of the entire specification;

[0196] ii) Mixtures according to any one of A22 - A25 or the disclosure from Sections 4, 3, and 1 and any combination of the entire specification;

[0197] iii) An aqueous dispersion according to any one of A26 - A34;

[0198] iv) Particles according to any one of A35 to A36 or the disclosure from Sections 4, 3, and 1 and any combination of the entire specification;

[0199] v) An aqueous composition according to any one of A37 - A44 or the disclosure from Sections 4, 3, and 1 and any combination of the entire specification.

[0200] Use of any one or any combination of the following for coatings, paints, inks, varnishes, lubricants, adhesives, additive manufacturing, 3D printing, textiles, waxes, fuels, photography, plastics, medical compositions, medical devices:

[0201] i) Particles according to A1a and any one of A1 - A21 or the disclosure from Sections 4, 3, and 1 and any combination of the entire specification;

[0202] ii) Mixtures according to any one of A22 - A25 or the disclosure from Sections 4, 3, and 1 and any combination of the entire specification;

[0203] iii) An aqueous dispersion according to any one of A26 - A34 or the disclosure from Sections 4, 3, and 1 and any combination of the entire specification;

[0204] iv) Particles according to any one of A35 - A36 or the disclosure from Sections 4, 3, and 1 and any combination of the entire specification;

[0205] v) An aqueous composition according to any one of A37 to A44 or any combination of the disclosure from Sections 4, 3, and 1 and the entire specification;

[0206] vi) A kit of parts according to A45 or any combination of the disclosure from Sections 4, 3, and 1 and the entire specification;

[0207] vii) A cured form according to any one of A46 to A51 or any combination of the disclosure from Sections 4, 3, and 1 and the entire specification;

[0208] viii) An article according to any one of A52 to A53 or any combination of the disclosure from Sections 4, 3, and 1 and the entire specification.

[0209] All combinations of the minimum and maximum values of the parameters disclosed in this specification can be used to define the parameter ranges of various preferments or embodiments of the present invention.

[0210] Unless otherwise expressly stated, any feature, element, component, embodiment, aspect, range, and in particular any preferred feature, preferred element, preferred embodiment, preferred aspect, preferred range, and the preferred combination of ranges, preferential options, embodiments, and aspects disclosed in any one of A1a or A1 to A55 in relation to any disclosure can be combined with each other and can be combined with any other feature, element, component, embodiment, aspect, range, and in particular any preferred feature, preferred element, preferred embodiment, preferred aspect, preferred range, and the preferred combination of ranges, preferential options, embodiments, and aspects of the present invention disclosed throughout this specification.

[0211] Unless otherwise expressly stated, any feature, element, component, embodiment, aspect, range, and in particular any preferred feature, preferred element, preferred embodiment, preferred aspect, preferred range, and the preferred combination of ranges, preferential options, embodiments, and aspects of the present invention disclosed throughout this specification can be combined with each other.

[0212] Definitions

[0213] 'Aziridine ring' means in the specification a 3 - membered ring system consisting of one nitrogen atom and two carbon atoms.

[0214] 'Organic particle' means a particle that does not contain any inorganic components. In other words, the particle contains no inorganic components.

[0215] The term'saturated alkylene group' means a divalent organic group formed by removing two hydrogen atoms from a saturated hydrocarbon, the free valences of which do not participate in double bonds. Exemplary alkylene groups include, but are not limited to, methylene.

[0216] The term 'unsaturated' means that the relevant entity does not contain any unsaturated groups.

[0217] The term 'ionic functional group' as used herein means a functional group that contains one or both of a cation and an anion, and the functional group is covalently bonded to the entity with which it is associated.

[0218] 'Poor chemical resistance' with respect to a cured coating (film) in this specification means that the chemical resistance of the film, as measured as described in the specification, is at most 1 [rating scale 0 - 5, where 5 represents the best performance and 0 represents the worst performance, and the rating scale is as disclosed in the specification].

[0219] 'Reasonable chemical resistance' with respect to a cured coating (film) in this specification means that the chemical resistance of the film, as measured as described in the specification, is 2 [rating scale 0 - 5, where 5 represents the best performance and 0 represents the worst performance, and the rating scale is as disclosed in the specification].

[0220] 'Good chemical resistance' with respect to a cured coating (film) in this specification means that the chemical resistance of the film, as measured as described in the specification, is 3 [rating scale 0 - 5, where 5 represents the best performance and 0 represents the worst performance, and the rating scale is as disclosed in the specification].

[0221] 'Very good chemical resistance' with respect to a cured coating (film) in this specification means that the chemical resistance of the film, as measured as described in the specification, is 4 [rating scale 0 - 5, where 5 represents the best performance and 0 represents the worst performance, and the rating scale is as disclosed in the specification].

[0222] 'Excellent chemical resistance' with respect to a cured coating (film) in this specification means that the chemical resistance of the film, as measured as described in the specification, is 5 [rating scale 0 - 5, where 5 represents the best performance and 0 represents the worst performance, and the rating scale is as disclosed in the specification].

[0223] 'Initial chemical resistance' with respect to an entity in this specification means the chemical resistance of the entity determined after the entity is prepared and before the entity is to be stored at 50 °C for 4 weeks - as so defined and determined in the specification (see step 1 of the method entitled 'Evaluation of Storage Stability and Crosslinking Efficiency', and the method entitled 'Evaluation of Chemical Resistance', both methods are described in the examples).

[0224] 'Final chemical resistance' of an entity in this specification means the chemical resistance of the entity determined after the entity has been stored at 50 °C for 4 weeks - as defined and determined in this specification (see step 2 of the method entitled 'Assessment of storage stability and crosslinking efficiency', and the method entitled 'Assessment of chemical resistance', both methods are described in the examples). The final chemical resistance can be equal to or lower than the initial chemical resistance.

[0225] 'Poor crosslinking efficiency' of an entity in this specification means that the entity has poor final chemical resistance, or equivalently, the final chemical resistance of the entity is poor.

[0226] 'Reasonable crosslinking efficiency' of an entity in this specification means that the entity has reasonable final chemical resistance, or equivalently, the final chemical resistance of the entity is reasonable.

[0227] 'Good crosslinking efficiency' of an entity in this specification means that the entity has good final chemical resistance, or equivalently, the final chemical resistance of the entity is good.

[0228] 'Very good crosslinking efficiency' of an entity in this specification means that the entity has very good final chemical resistance, or equivalently, the final chemical resistance of the entity is very good.

[0229] 'Excellent crosslinking efficiency' of an entity in this specification means that the entity has excellent final chemical resistance, or equivalently, the final chemical resistance of the entity is excellent.

[0230] 'Initial viscosity' (or equivalently 'initial apparent viscosity') of an entity in this specification means the viscosity of the entity determined after the entity is prepared and before the entity is to be stored at 50 °C for 4 weeks - as defined and determined in this specification (see step 1 of the method entitled 'Assessment of storage stability and crosslinking efficiency', and the method entitled 'Assessment of viscosity', both methods are described in the examples).

[0231] 'Final viscosity' (or equivalently 'final apparent viscosity') of an entity in this specification means the viscosity of the entity determined after the entity has been stored at 50 °C for 4 weeks - as defined and determined in this specification (see step 2 of the method entitled 'Assessment of storage stability and crosslinking efficiency', and the method entitled 'Assessment of viscosity', both methods are described in the examples). The final viscosity can be equal to or higher than the initial viscosity.

[0232] The "easy - process viscosity" of an entity as used in this specification means that the end viscosity (as defined and measured in this specification) is at most 20 times the starting viscosity (as defined and measured in this specification) (or equivalently, the ratio of end viscosity / starting viscosity is at most 20), preferably at most 19 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 19), more preferably at most 18 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 18), for example at most 17 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 17), for example at most 16 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 16), for example at most 15 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 15), for example at most 14 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 14), for example at most 13 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 13), for example at most 12 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 12), for example at most 11 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 11), for example at most 10 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 10), for example at most 9 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 9), for example at most 8 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 8), for example at most 7 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 7), for example at most 6 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 6), for example at most 5 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 5), for example at most 4 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 4), for example at most 3 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 3), for example at most 2 times the starting viscosity (or equivalently, the ratio of end viscosity / starting viscosity is at most 2).

[0233] The "enhanced storage stability" of an entity (or equivalently "enhanced storage stability at elevated temperatures for an extended period") as used in this specification means that the entity has:

[0234] i) The easy - process viscosity (as defined in this specification), and ii) The end chemical resistance is at most 3 rating points lower than the starting chemical resistance, preferably at most 2 rating points lower than the starting chemical resistance, more preferably at most 1 rating point lower than the starting chemical resistance, and most preferably the end chemical resistance is equal to the starting chemical resistance.

[0235] "For an extended period of time at an elevated temperature" means a period of 4 weeks at a temperature of 50 °C.

[0236] ‘Room temperature’ means 23 ± 1 °C herein.

[0237] ‘Atmospheric pressure’ means a pressure of 1 atm in this specification.

[0238] ‘Standard conditions’ means the collective term for room temperature and atmospheric pressure in this specification.

[0239] ‘Less than’ means in this specification that the relevant maximum boundary value is not included within the range.

[0240] ‘Greater than’ means in this specification that the relevant minimum boundary value is not included within the range.

[0241] ‘Rpm’ means revolutions per minute.

[0242] ‘Polyacrylic acid’ means in this specification any polymer containing reaction residues of acrylic acid and / or methacrylic acid and / or acrylate and / or methacrylate, and / or styrene, and / or acrylonitrile, and / or acrylamide, and / or itaconate, and / or itaconic acid, and / or divinylbenzene, and / or methacrylonitrile, and / or vinyl ester, and / or vinyl halide, and / or fumarate, and / or fumaric acid; preferably, ‘polyacrylic acid’ means in this specification any polymer consisting of reaction residues of acrylic acid and / or methacrylic acid and / or acrylate and / or methacrylate, and / or styrene, and / or acrylonitrile, and / or acrylamide, and / or itaconate, and / or itaconic acid, and / or divinylbenzene, and / or methacrylonitrile, and / or vinyl ester and / or vinyl halide, and / or fumarate and / or fumaric acid.

[0243] ‘Epoxy proton’ means in this specification two protons of the methylene (-CH2-) group of an ethylene oxide (also known as epoxy) group having the following formula

[0244]

[0245] ‘Curing’ means in the specification the process of becoming ‘fixed’ to form an irreversible cross-linked network (the so-called ‘cured form’ or ‘cured composition’), where the material no longer flows, melts or dissolves. In this context, the terms ‘curing’ and ‘cross-linking’ are used interchangeably. Curing can be carried out under standard conditions (as defined in this specification), or by using heat, or by using pressure, or by applying a vacuum, or by radiation such as ultraviolet radiation, or by any combination thereof.

[0246] The decimal separator (also known as the radix character) in numbers is represented by a period (‘.’).

[0247] 1. Particles of the present invention

[0248] The particles of the present invention are disclosed throughout the specification. As used in this specification, the term 'particles of the present invention' (or alternatively 'particles of the present invention') includes any and all of its preferred options, combinations of its features and scopes, and combinations of any and all of its preferred options with any and all combinations of its features and scopes. Thus, any and all particles of the present invention disclosed in Subsection 1 and its subsections include any and all of its priority items, combinations of its features and scopes, and combinations of any and all of its priority items with any and all combinations of its features and scopes - throughout the specification - are collectively referred to as particles of the present invention (or equivalently referred to as particles of the present invention). Each and all components of the particles of the present invention are described in detail in Subsection 1.

[0249] The particles of the present invention are according to any one of A1a or A1 to A21 or any combination disclosed throughout the specification. More specifically, the particles - preferably organic particles - comprise an (aziridinylhydroxy)-functional organic component (AZ component),

[0250] and wherein

[0251] The particles have a size, as determined by dynamic light scattering according to the specification, of at least 2 nm and at most 3000 nm, preferably at least 2 nm and at most 2500 nm, more preferably at least 2 nm and at most 2000 nm, even more preferably at least 2 nm and at most 1500 nm, such as at least 2 nm and at most 1000 nm, such as at least 2 nm and at most 900 nm, such as at least 2 nm and at most 800 nm, such as at least 2 nm and at most 600 nm, such as at least 2 nm and at most 500 nm, such as at least 2 nm and at most 400 nm, such as at least 2 nm and at most 350 nm, such as at least 2 nm and at most 300 nm, such as at least 10 nm and at most 3000 nm, such as at least 10 nm and at most 2500 nm, such as at least 10 nm and at most 2000 nm, such as at least 10 nm and at most 1500 nm, such as at least 10 nm and at most 1000 nm, such as at least 10 nm and at most 900 nm, such as at least 10 nm and at most 800 nm, such as at least 10 nm and at most 600 nm, such as at least 10 nm and at most 500 nm, such as at least 10 nm and at most 400 nm, such as at least 10 nm and at most 350 nm, such as at least 10 nm and at most 300 nm, such as at least 20 nm and at most 3000 nm, such as at least 20 nm and at most 2500 nm, such as at least 20 nm and at most 2000 nm, such as at least 20 nm and at most 1500 nm, such as at least 20 nm and at most 1000 nm, such as at least 20 nm and at most 900 nm, such as at least 20 nm and at most 800 nm, such as at least 20 nm and at most 600 nm, such as at least 20 nm and at most 500 nm, such as at least 20 nm and at most 400 nm, such as at least 20 nm and at most 350 nm, such as at least 20 nm and at most 300 nm, such as at least 30 nm and at most 3000 nm, such as at least 30 nm and at most 2500 nm, such as at least 30 nm and at most 2000 nm, such as at least 30 nm and at most 1500 nm, such as at least 30 nm and at most 1000 nm, such as at least 30 nm and at most 900 nm, such as at least 30 nm and at most 800 nm, such as at least 30 nm and at most 600 nm, such as at least 30 nm and at most 500 nm, such as at least 30 nm and at most 400 nm, such as at least 30 nm and at most 350 nm, such as at least 30 nm and at most 300 nm, such as at least 40 nm and at most 3000 nm, such as at least 40 nm and at most 2500 nm, such as at least 40 nm and at most 2000 nm, such as at least 40 nm and at most 1500 nm, such as at least 40 nm and at most 1000 nm, such as at least 40 nm and at most 900 nm, such as at least 40 nm and at most 800 nm, such as at least 40 nm and at most 600 nm,For example, at least 40 nm and at most 500 nm, for example, at least 40 nm and at most 400 nm, for example, at least 40 nm and at most 350 nm, for example, at least 40 nm and at most 300 nm, for example, at least 50 nm and at most 3000 nm, for example, at least 50 nm and at most 2500 nm, for example, at least 50 nm and at most 2000 nm, for example, at least 50 nm and at most 1500 nm, for example, at least 50 nm and at most 1000 nm, for example, at least 50 nm and at most 900 nm, for example, at least 50 nm and at most 800 nm, for example, at least 50 nm and at most 600 nm, for example, at least 50 nm and at most 500 nm, for example, at least 50 nm and at most 400 nm, for example, at least 50 nm and at most 350 nm, for example, at least 50 nm and at most 300 nm, for example, at least 60 nm and at most 3000 nm, for example, at least 60 nm and at most 2500 nm, for example, at least 60 nm and at most 2000 nm, for example, at least 60 nm and at most 1500 nm, for example, at least 60 nm and at most 1000 nm, for example, at least 60 nm and at most 900 nm, for example, at least 60 nm and at most 800 nm, for example, at least 60 nm and at most 600 nm, for example, at least 60 nm and at most 500 nm, for example, at least 60 nm and at most 400 nm, for example, at least 60 nm and at most 350 nm, for example, at least 60 nm and at most 300 nm, for example, at least 70 nm and at most 3000 nm, for example, at least 70 nm and at most 2500 nm, for example, at least 70 nm and at most 2000 nm, for example, at least 70 nm and at most 1500 nm, for example, at least 70 nm and at most 1000 nm, for example, at least 70 nm and at most 900 nm, for example, at least 70 nm and at most 800 nm, for example, at least 70 nm and at most 600 nm, for example, at least 70 nm and at most 500 nm, for example, at least 70 nm and at most 400 nm, for example, at least 70 nm and at most 350 nm, for example, at least 70 nm and at most 300 nm, for example, at least 80 nm and at most 3000 nm, for example, at least 80 nm and at most 2500 nm, for example, at least 80 nm and at most 2000 nm, for example, at least 80 nm and at most 1500 nm, for example, at least 80 nm and at most 1000 nm, for example, at least 80 nm and at most 900 nm, for example, at least 80 nm and at most 800 nm, for example, at least 80 nm and at most 600 nm, for example, at least 80 nm and at most 500 nm, for example, at least 80 nm and at most 400 nm, for example, at least 80 nm and at most 350 nm, for example, at least 80 nm and at most 300 nm, for example, at least 90 nm and at most 3000 nm, for example, at least 90 nm and at most 2500 nm, for example, at least 90 nm and at most 2000 nm, for example, at least 90 nm and at most 1500 nm, for example, at least 90 nm and at most 1000 nmFor example, an average hydrodynamic diameter (D, H ) based on scattering intensity of at least 90 nm and at most 900 nm, such as at least 90 nm and at most 800 nm, such as at least 90 nm and at most 600 nm, such as at least 90 nm and at most 500 nm, such as at least 90 nm and at most 400 nm, such as at least 90 nm and at most 350 nm, such as at least 90 nm and at most 300 nm, such as at least 100 nm and at most 3000 nm, such as at least 100 nm and at most 2500 nm, such as at least 100 nm and at most 2000 nm, such as at least 100 nm and at most 1500 nm, such as at least 100 nm and at most 1000 nm, such as at least 100 nm and at most 900 nm, such as at least 100 nm and at most 800 nm, such as at least 100 nm and at most 600 nm, such as at least 100 nm and at most 500 nm, such as at least 100 nm and at most 400 nm, such as at least 100 nm and at most 350 nm, such as at least 100 nm and at most 300 nm,

[0252] and

[0253] wherein the (aziridinylhydroxy)-functional organic component (AZ component) is selected from the group consisting of the following i) to vi): i) an (aziridinylhydroxy)-functional organic compound AZ1 of formula A1 having only two aziridine rings (AZ1 compound); ii) an (aziridinylhydroxy)-functional organic compound AZ2 of formula A2 having only three aziridine rings (AZ2 compound); iii) an (aziridinylhydroxy)-functional organic compound AZ3 of formula A3 having only four aziridine rings (AZ3 compound); iv) an (aziridinylhydroxy)-functional organic compound AZ4 of formula A4 having only five aziridine rings (AZ4 compound); v) an (aziridinylhydroxy)-functional organic compound AZ5 of formula A5 having only six aziridine rings (AZ5 compound); and vi) mixtures thereof. Preferably, the AZ component is selected from the group consisting of the following i) to iv): i) an (aziridinylhydroxy)-functional organic compound AZ1 of formula A1 having only two aziridine rings (AZ1 compound); ii) an (aziridinylhydroxy)-functional organic composition AZ2 of formula A2 having only three aziridine rings (AZ2 compound); iii) an (aziridinylhydroxy)-functional organic compound AZ3 of formula A3 having only four aziridine rings (AZ3 compound); and iv) mixtures thereof,

[0254]

[0255] where

[0256] X1 is a divalent aliphatic organic group or a divalent aromatic organic group, preferably X1 is a divalent aliphatic organic group;

[0257] X2 is a trivalent aliphatic organic group or a trivalent aromatic organic group, preferably X2 is a trivalent aliphatic organic group;

[0258] X3 is a tetravalent aliphatic organic group or a tetravalent aromatic organic group, preferably X3 is a tetravalent aliphatic organic group;

[0259] X4 is a pentavalent aliphatic organic group or a pentavalent aromatic organic group, preferably X4 is a pentavalent aliphatic organic group;

[0260] X5 is a hexavalent aliphatic organic group or a hexavalent aromatic organic group, preferably X5 is a hexavalent aliphatic organic group;

[0261] And wherein each of said X1 to X5 consists of a set of covalently linked atoms in a configuration comprising a straight chain and / or a branched chain and / or a cyclic structure, preferably consisting of a straight chain and / or a branched chain and / or a cyclic structure, said set of atoms being selected from the group consisting of the following i) to x): i) carbon and hydrogen atoms, ii) carbon, hydrogen and oxygen atoms, iii) carbon, hydrogen and nitrogen atoms, iv) carbon, hydrogen and sulfur atoms, v) carbon, hydrogen, oxygen and nitrogen atoms, vi) carbon, hydrogen, nitrogen and sulfur atoms, vii) carbon, hydrogen, oxygen and sulfur atoms, viii) carbon, hydrogen, oxygen, nitrogen and sulfur atoms, ix) carbon, hydrogen and silicon atoms, and x) carbon, hydrogen, oxygen and silicon atoms, and xi) any combination of ix) and / or x) with any one or all of iii) to viii),

[0262] And wherein each of said X1 to X5 has carbon atoms and hydrogen atoms,

[0263] And wherein each of said X1 to X5 optionally has oxygen atoms and / or nitrogen atoms and / or sulfur atoms and / or silicon atoms,

[0264] And wherein X1 and / or X2 and / or X3 and / or X4 and / or X5 may optionally contain ionic functional groups, preferably X1 and / or X2 and / or X3 and / or X4 and / or X5 do not contain ionic functional groups,

[0265] And wherein

[0266] Y is a monovalent organic group selected from the group consisting of: i) a monovalent (aziridinylhydroxyisopropyl) organic group of formula B1, ii) a monovalent (aziridinylhydroxycyclohexane) organic group of formula B2, and iii) a monovalent (aziridinylhydroxycyclohexane) organic group of formula B3, preferably Y is a monovalent (aziridinylhydroxyisopropyl) organic group of formula B1,

[0267]

[0268]

[0269] and wherein

[0270] R1 is selected from the group consisting of: hydrogen and methyl; and

[0271] R2 is selected from the group consisting of: hydrogen, methyl and C2-C5 alkyl; and

[0272] R3 is selected from the group consisting of: methyl and C2-C4 alkyl; and

[0273] R4 is selected from the group consisting of: hydrogen, methyl and C2-C4 alkyl;

[0274] and wherein

[0275] Y in each of the compounds A1 to A5 may be the same as or different from each other, and wherein each of the single covalent bonds between said Y and each of said X1 to X5 is selected from the group consisting of: carbon-carbon single bond, carbon-oxygen single bond and carbon-nitrogen single bond, preferably carbon-oxygen single bond and carbon-nitrogen single bond, more preferably carbon-oxygen single bond,

[0276] and wherein

[0277] Each of the AZ1 compounds to AZ5 compounds has a molecular weight of at least 600 Da and at most 10,000 Da as determined by MALDI-TOF MS according to the specification.

[0278] Preferably, the particles of the present invention comprise at least 20% by weight, preferably at least 40% by weight, more preferably at least 55% by weight, even more preferably at least 70% by weight, such as at least 82% by weight, such as at least 85% by weight, such as at least 89% by weight, such as at least 93% by weight, such as at least 96% by weight, such as at least 99% by weight of the (aziridinylhydroxy)-functional organic component (AZ component).

[0279] Preferably, the molecular weight of each of the compounds AZ1 to AZ5 is at least 600 Da and at most 8000 Da, preferably at least 600 Da and at most 7000 Da, more preferably at least 600 Da and at most 6000 Da, such as at least 600 Da and at most 5500 Da, such as at least 600 Da and at most 5000 Da, such as at least 600 Da and at most 4000 Da, such as at least 600 Da and at most 3500 Da, such as at least 600 Da and at most 3200 Da, such as at least 600 Da and at most 3000 Da, such as at least 600 Da and at most 2500 Da, such as at least 600 Da and at most 2200 Da, such as at least 600 Da and at most 2000 Da, such as at least 630 Da and at most 10000 Da, preferably at least 630 Da and at most 8000 Da, more preferably at least 630 Da and at most 7000 Da, even more preferably at least 630 Da and at most 6000 Da, such as at least 630 Da and at most 5500 Da, such as at least 630 Da and at most 5000 Da, such as at least 630 Da and at most 4000 Da, such as at least 630 Da and at most 3500 Da, such as at least 630 Da and at most 3200 Da, such as at least 630 Da and at most 3000 Da, such as at least 630 Da and at most 2500 Da, such as at least 630 Da and at most 2200 Da, such as at least 630 Da and at most 2000 Da, such as at least 640 Da and at most 10000 Da, such as at least 640 Da and at most 8000 Da, such as at least 640 Da and at most 7000 Da, such as at least 640 Da and at most 6000 Da, such as at least 640 Da and at most 5500 Da, such as at least 640 Da and at most 5000 Da, such as at least 640 Da and at most 4000 Da, such as at least 640 Da and at most 3500 Da, such as at least 640 Da and at most 3200 Da, such as at least 640 Da and at most 3000 Da, such as at least 640 Da and at most 2500 Da, such as at least 640 Da and at most 2200 Da, such as at least 640 Da and at most 2000 Da, such as at least 650 Da and at most 10000 Da, such as at least 650 Da and at most 8000 Da, such as at least 650 Da and at most 7000 Da, such as at least 650 Da and at most 6000 Da, such as at least 650 Da and at most 5500 Da, such as at least 650 Da and at most 5000 Da, such as at least 650 Da and at most 4000 Da, such as at least 650 Da and at most 3500 Da, such as at least 650 Da and at most 3200 Da, such as at least 650 Da and at most 3000 Da, such as at least 650 Da and at most 2500 Da, such as at least 650 Da and at most 2200 Da,For example, at least 650 Da and at most 2000 Da, such as at least 700 Da and at most 10000 Da, such as at least 700 Da and at most 8000 Da, such as at least 700 Da and at most 7000 Da, such as at least 700 Da and at most 6000 Da, such as at least 700 Da and at most 5500 Da, such as at least 700 Da and at most 5000 Da, such as at least 700 Da and at most 4000 Da, such as at least 700 Da and at most 3500 Da, such as at least 700 Da and at most 3200 Da, such as at least 700 Da and at most 3000 Da, such as at least 700 Da and at most 2500 Da, such as at least 700 Da and at most 2200 Da, such as at least 700 Da and at most 2000 Da, such as at least 750 Da and at most 10000 Da, such as at least 750 Da and at most 8000 Da, such as at least 750 Da and at most 7000 Da, such as at least 750 Da and at most 6000 Da, such as at least 750 Da and at most 5500 Da, such as at least 750 Da and at most 5000 Da, such as at least 750 Da and at most 4000 Da, such as at least 750 Da and at most 3500 Da, such as at least 750 Da and at most 3200 Da, such as at least 750 Da and at most 3000 Da, such as at least 750 Da and at most 2500 Da, such as at least 750 Da and at most 2200 Da, such as at least 750 Da and at most 2000 Da, such as at least 800 Da and at most 10000 Da, such as at least 800 Da and at most 8000 Da, such as at least 800 Da and at most 7000 Da, such as at least 800 Da and at most 6000 Da, such as at least 800 Da and at most 5500 Da, such as at least 800 Da and at most 5000 Da, such as at least 800 Da and at most 4000 Da, such as at least 800 Da and at most 3500 Da, such as at least 800 Da and at most 3200 Da, such as at least 800 Da and at most 3000 Da, such as at least 800 Da and at most 2500 Da, such as at least 800 Da and at most 2200 Da, such as at least 800 Da and at most 2000 Da, such as at least 850 Da and at most 10000 Da, such as at least 850 Da and at most 8000 Da, such as at least 850 Da and at most 7000 Da, such as at least 850 Da and at most 6000 Da, such as at least 850 Da and at most 5500 Da, such as at least 850 Da and at most 5000 Da, such as at least 850 Da and at most 4000 Da, such as at least 850 Da and at most 3500 Da, such as at least 850 Da and at most 3200 Da, such as at least 850 Da and at most 3000 Da, such as at least 850 Da and at most 2500 Da, such as at least 850 Da and at most 2200 DaFor example, at least 850 Da and at most 2000 Da, for example, at least 900 Da and at most 10000 Da, for example, at least 900 Da and at most 8000 Da, for example, at least 900 Da and at most 7000 Da, for example, at least 900 Da and at most 6000 Da, for example, at least 900 Da and at most 5500 Da, for example, at least 900 Da and at most 5000 Da, for example, at least 900 Da and at most 4000 Da, for example, at least 900 Da and at most 3500 Da, for example, at least 900 Da and at most 3200 Da, for example, at least 900 Da and at most 3000 Da, for example, at least 900 Da and at most 2500 Da, for example, at least 900 Da and at most 2200 Da, for example, at least 900 Da and at most 2000 Da, for example, at least 950 Da and at most 10000 Da, for example, at least 950 Da and at most 8000 Da, for example, at least 950 Da and at most 7000 Da, for example, at least 950 Da and at most 6000 Da, for example, at least 950 Da and at most 5500 Da, for example, at least 950 Da and at most 5000 Da, for example, at least 950 Da and at most 4000 Da, for example, at least 950 Da and at most 3500 Da, for example, at least 950 Da and at most 3200 Da, for example, at least 950 Da and at most 3000 Da, for example, at least 950 Da and at most 2500 Da, for example, at least 950 Da and at most 2200 Da, for example, at least 950 Da and at most 2000 Da, for example, at least 1000 Da and at most 10000 Da, for example, at least 1000 Da and at most 8000 Da, for example, at least 1000 Da and at most 7000 Da, for example, at least 1000 Da and at most 6000 Da, for example, at least 1000 Da and at most 5500 Da, for example, at least 1000 Da and at most 5000 Da, for example, at least 1000 Da and at most 4000 Da, for example, at least 1000 Da and at most 3500 Da, for example, at least 1000 Da and at most 3200 Da, for example, at least 1000 Da and at most 3000 Da, for example, at least 1000 Da and at most 2500 Da, for example, at least 1000 Da and at most 2200 Da, for example, at least 1000 Da and at most 2000 Da, for example, at least 1100 Da and at most 10000 Da, for example, at least 1100 Da and at most 8000 Da, for example, at least 1100 Da and at most 7000 Da, for example, at least 1100 Da and at most 6000 Da, for example, at least 1100 Da and at most 5500 Da, for example, at least 1100 Da and at most 5000 Da, for example, at least 1100 Da and at most 4000 Da, for example, at least 1100 Da and at most 3500 Da, for example, at least 1100 Da and at most 3200 Da, for example, at least 1100 Da and at most 3000 Da, for example, at least 1100 Da and at most 2500 DaFor example, at least 1100 Da and at most 2200 Da, for example at least 1100 Da and at most 2000 Da, for example at least 1200 Da and at most 10000 Da, for example at least 1200 Da and at most 8000 Da, for example at least 1200 Da and at most 7000 Da, for example at least 1200 Da and at most 6000 Da, for example at least 1200 Da and at most 5500 Da, for example at least 1200 Da and at most 5000 Da, for example at least 1200 Da and at most 4000 Da, for example at least 1200 Da and at most 3500 Da, for example at least 1200 Da and at most 3200 Da, for example at least 1200 Da and at most 3000 Da, for example at least 1200 Da and at most 2500 Da, for example at least 1200 Da and at most 2200 Da, for example at least 1200 Da and at most 2000 Da.

[0280] Preferably, X1 is a divalent aliphatic organic group or a divalent aromatic organic group that is different from the divalent group of bisphenol A.

[0281] Preferably, X1 is a divalent aliphatic organic group or a divalent aromatic organic group that is different from the divalent organic groups selected from the group consisting of: the divalent group of bisphenol A, the divalent group of bisphenol AP, the divalent group of bisphenol AF, the divalent group of bisphenol B, the divalent group of bisphenol BP, the divalent group of bisphenol C, the divalent group of bisphenol C2, the divalent group of bisphenol E, the divalent group of bisphenol F, the divalent group of bisphenol G, the divalent group of bisphenol M, the divalent group of bisphenol S, the divalent group of bisphenol P, the divalent group of bisphenol PH, the divalent group of bisphenol TMC, the divalent group of bisphenol Z, the divalent group of dinitrobisphenol A, the divalent group of tetrabromobisphenol A, and combinations thereof. Preferably, X1 is a divalent aliphatic organic group.

[0282] Preferably, X1 and / or X2 and / or X3 and / or X4 and / or X5 contains at least one structural unit or combination of structural units selected from the group consisting of: Unit 1, Unit 2, Unit 3, Unit 4, Unit 5, Unit 6, Unit 7, Unit 8, Unit 9, Unit 10, and Unit 11. Preferably, it contains at least one structural unit or combination of structural units selected from the group consisting of: Unit 1, Unit 4, Unit 9, Unit 10, and Unit 11. Units 1 to 11 are depicted below:

[0283]

[0284]

[0285] where

[0286] R' is selected from the group consisting of: hydrogen and methyl; and

[0287] j is an integer in the range from 1 to 5, preferably from 1 to 3; and

[0288] n is an integer ranging from and including 2 up to and including 50, preferably from and including 2 up to and including 40, more preferably from and including 2 up to and including 30, most preferably from and including 2 up to and including 20, such as from and including 2 up to and including 15, such as from and including 2 up to and including 10, such as from and including 2 up to and including 5 (e.g., n is 2), such as from and including 3 up to and including 50, such as from and including 3 up to and including 40, such as from and including 3 up to and including 30, such as from and including 3 up to and including 20, such as from and including 3 up to and including 15, such as from and including 3 up to and including 10, such as from and including 3 up to and including 5 (e.g., n is 3), such as from and including 4 up to and including 50, such as from and including 4 up to and including 40, such as from and including 4 up to and including 30, such as from and including 4 up to and including 20, such as from and including 4 up to and including 15, such as from and including 4 up to and including 10, such as from and including 4 up to and including 5 (e.g., n is 4), such as from and including 5 up to and including 50, such as from and including 5 up to and including 40, such as from and including 5 up to and including 30, such as from and including 5 up to and including 20, such as from and including 5 up to and including 15, such as from and including 5 up to and including 10 (e.g., n is 5), such as from and including 6 up to and including 50, such as from and including 6 up to and including 40, such as from and including 6 up to and including 30, such as from and including 6 up to and including 20, such as from and including 6 up to and including 15, such as from and including 6 up to and including 10 (e.g., n is 6), such as from and including 7 up to and including 50, such as from and including 7 up to and including 40, such as from and including 7 up to and including 30, such as from and including 7 up to and including 20, such as from and including 7 up to and including 15, such as from and including 7 up to and including 10 (e.g., n is 7), such as from and including 8 up to and including 50, such as from and including 8 up to and including 40, such as from and including 8 up to and including 30, such as from and including 8 up to and including 20, such as from and including 8 up to and including 15, such as from and including 8 up to and including 10 (e.g., n is 8), such as from and including 9 up to and including 50, such as from and including 9 up to and including 40, such as from and including 9 up to and including 30, such as from and including 9 up to and including 20, such as from and including 9 up to and including 15, such as from and including 9 up to and including 10 (e.g., n is 9), such as from and including 10 up to and including 50, such as from and including 10 up to and including 40, such as from and including 10 up to and including 30, such as from and including 10 up to and including 20, such as from and including 10 up to and including 15 (e.g., n is 10).

[0289] Preferably,

[0290] R1 is selected from the group consisting of: hydrogen and methyl; and

[0291] R2 is selected from the group consisting of: hydrogen, methyl and ethyl; and

[0292] R3 is selected from the group consisting of: methyl and C2-C4 alkyl; and

[0293] R4 is selected from the group consisting of: hydrogen, methyl and ethyl.

[0294] Preferably, the aggregation number of carbon atoms in R1, R2, R3 and R4 is at most 9, preferably at most 4, more preferably at most 2, for example at most 1.

[0295] Preferably, X1 and / or X2 and / or X3 and / or X4 and / or X5 do not contain one or any combination of the following structural units BP1, BP2, BP3 and BS

[0296]

[0297] Preferably, X1 and / or X2 and / or X3 and / or X4 and / or X5 contain at least one unit 11 as a structural unit.

[0298] Preferably, X1 is a divalent aliphatic organic group of formula A1a'

[0299]

[0300] wherein

[0301] R' is selected from the group consisting of: hydrogen and methyl; and

[0302] j is an integer in the range from 1 to 5, preferably from 1 to 3; and

[0303] n is an integer in the range from and including 2 up to and including 50, preferably from and including 2 up to and including 40, more preferably from and including 2 up to and including 30, most preferably from and including 2 up to and including 20, for example from and including 2 up to and including 15, for example from and including 2 up to and including 10, for example from and including 2 up to and including 5 (e.g., n is 2), for example from and including 3 up to and including 50, for example from and including 3 up to and including 40, for example from and including 3 up to and including 30, for example from and including 3 up to and including 20, for example from and including 3 up to and including 15, for example from and including 3 up to and including 10, for example from and including 3 up to and including 5 (e.g., n is 3), for example from and including 4 up to and including 50, for example from and including 4 up to and including 40, for example from and including 4 up to and including 30, for example from and including 4 up to and including 20, for example from and including 4 up to and including 15, for example from and including 4 up to and including 10, for example from and including 4 up to and including 5 (e.g., n is 4), for example from and including 5 up to and including 50, for example from and including 5 up to and including 40, for example from and including 5 up to and including 30, for example from and including 5 up to and including 20, for example from and including 5 up to and including 15, for example from and including 5 up to and including 10 (e.g., n is 5), for example from and including 6 up to and including 50, for example from and including 6 up to and including 40, for example from and including 6 up to and including 30, for example from and including 6 up to and including 20, for example from and including 6 up to and including 15, for example from and including 6 up to and including 10 (e.g., n is 6), for example from and including 7 up to and including 50, for example from and including 7 up to and including 40, for example from and including 7 up to and including 30, for example from and including 7 up to and including 20, for example from and including 7 up to and including 15, for example from and including 7 up to and including 10 (e.g., n is 7), for example from and including 8 up to and including 50, for example from and including 8 up to and including 40, for example from and including 8 up to and including 30, for example from and including 8 up to and including 20, for example from and including 8 up to and including 15, for example from and including 8 up to and including 10 (e.g., n is 8), for example from and including 9 up to and including 50, for example from and including 9 up to and including 40, for example from and including 9 up to and including 30, for example from and including 9 up to and including 20, for example from and including 9 up to and including 15, for example from and including 9 up to and including 10 (e.g., n is 9), for example from and including 10 up to and including 50, for example from and including 10 up to and including 40, for example from and including 10 up to and including 30, for example from and including 10 up to and including 20, for example from and including 10 up to and including 15 (e.g., n is 10).

[0304] Preferably, each of X1 to X5 contains only single covalent bonds, or both single covalent bonds and double covalent bonds, and wherein the single covalent bonds are selected from the group consisting of: carbon-carbon single bonds, carbon-hydrogen single bonds, carbon-nitrogen single bonds, carbon-sulfur single bonds, carbon-silicon single bonds, silicon-oxygen single bonds, nitrogen-hydrogen single bonds, sulfur-oxygen single bonds, carbon-oxygen single bonds where oxygen is bonded to hydrogen to form a hydroxyl group, silicon-oxygen-silicon single bonds, and wherein the double covalent bonds are selected from the group consisting of: carbon-carbon double bonds, carbon-nitrogen double bonds, sulfur-oxygen double bonds, carbon-oxygen double bonds.

[0305] Preferably, each of X1 to X5 contains only single covalent bonds, or both single covalent bonds and double covalent bonds, and wherein the single covalent bonds are selected from the group consisting of: carbon-carbon single bonds, carbon-hydrogen single bonds, carbon-nitrogen single bonds, carbon-sulfur single bonds, carbon-silicon single bonds, silicon-oxygen single bonds, nitrogen-hydrogen single bonds, sulfur-oxygen single bonds, carbon-oxygen single bonds where oxygen is bonded to hydrogen to form a hydroxyl group, silicon-oxygen-silicon single bonds, and wherein the double covalent bonds are selected from the group consisting of: carbon-carbon double bonds, carbon-nitrogen double bonds, sulfur-oxygen double bonds, carbon-oxygen double bonds where carbon is a member of a ring structure, and carbon-oxygen double bonds where carbon is bonded to two other carbons through a carbon-carbon single bond, carbon-oxygen double bonds where carbon is bonded to another oxygen through a single bond and to nitrogen through a single bond, carbon-oxygen double bonds where carbon is bonded to two nitrogens through a carbon-nitrogen single bond, carbon-oxygen double bonds where carbon is bonded to two other oxygens through a single bond.

[0306] Preferably, relative to the total number of atoms present in X1 and / or X2 and / or X3 and / or X4 and / or X5, the total number of carbon atoms and hydrogen atoms in X1 and / or X2 and / or X3 and / or X4 and / or X5 is at least 5%, preferably at least 10%, more preferably at least 15%, most preferably at least 20%, for example at least 25%, for example at least 30%, for example at least 35%, for example at least 40%, for example at least 45%, for example at least 50%, for example at least 55%, for example at least 60%, for example at least 65%, for example at least 70%, for example at least 75%, for example at least 80%, for example at least 85%, for example at least 90%, for example at least 95%, for example at least 97%, for example at least 98%, for example at least 99%, for example 100%.

[0307] Preferably, the total number of atoms present in X1 and / or X2 and / or X3 and / or X4 and / or X5 is at most 600, preferably at most 550, more preferably at most 500, most preferably at most 450, for example at most 400, for example at most 350, for example at most 300, for example at most 250, for example at most 200.

[0308] Preferably, the AZ component is selected from the group consisting of the following i) to v): i) (aziridinylhydroxy)-functional organic compound AZ1 of formula A1 (AZ1 compound), ii) (aziridinylhydroxy)-functional organic compound AZ2 of formula A2 (AZ2 compound), iii) (aziridinylhydroxy)-functional organic compound AZ3 of formula A3 (AZ3 compound), iv) (aziridinylhydroxy)-functional organic compound AZ5 of formula A5 (AZ5 compound), and vi) mixtures thereof, and

[0309] wherein

[0310] the AZ1 compound is selected from the group consisting of a compound of formula A1a and a compound of formula A1b, and each of these formulas A1a - A1d is as described below

[0311]

[0312] where each n in formula A1a is independently selected, and each n in formula A1a is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 10, more preferably from and including 2 up to and including 7, most preferably from and including 2 up to and including 5, for example from and including 2 up to and including 4, for example from and including 3 up to and including 20, for example from and including 3 up to and including 10, for example from and including 3 up to and including 7, for example from and including 3 up to and including 5, for example from and including 3 up to and including 4 (for example n equals 4); and

[0313]

[0314] where R in formula A1b is a C3 - C 10 saturated alkylene group, and where each n in formula A1b is independently selected, and each n in formula A1a is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 10, more preferably from and including 2 up to and including 7, most preferably from and including 2 up to and including 5, for example from and including 2 up to and including 4, for example from and including 3 up to and including 20, for example from and including 3 up to and including 10, for example from and including 3 up to and including 7, for example from and including 3 up to and including 5, for example from and including 3 up to and including 4 (for example n equals 4);

[0315] and

[0316]

[0317] Each n in formula A1c is independently selected, and each n in formula A1b is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 10, more preferably from and including 2 up to and including 7, most preferably from and including 2 up to and including 5, such as from and including 2 up to and including 4, such as from and including 3 up to and including 20, such as from and including 3 up to and including 10, such as from and including 3 up to and including 7, such as from and including 3 up to and including 5, such as from and including 3 up to and including 4 (e.g., n equals 4).

[0318] and

[0319]

[0320] wherein R in formula A1d is a C3-C 10 saturated alkylene group, and each n in formula A1d is independently selected, and each n in formula A1b is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 10, more preferably from and including 2 up to and including 7, most preferably from and including 2 up to and including 5, such as from and including 2 up to and including 4, such as from and including 3 up to and including 20, such as from and including 3 up to and including 10, such as from and including 3 up to and including 7, such as from and including 3 up to and including 5, such as from and including 3 up to and including 4 (e.g., n equals 4).

[0321] and

[0322] wherein

[0323] the AZ2 compound is selected from the group consisting of: a compound having formula A2a, a compound having formula A2b, a compound having formula A2c, a compound having formula A2d, a compound having formula A2e, each of these formulas A2a - A2e being described below

[0324]

[0325] wherein n in formula A2a is an integer ranging from and including 2 up to and including 20, such as from and including 2 up to and including 10, such as from and including 2 up to and including 8, such as from and including 3 up to and including 20, such as from and including 3 up to and including 10, such as from and including 3 up to and including 8, such as from and including 4 up to and including 20, such as from and including 4 up to and including 10, such as from and including 4 up to and including 8, such as from and including 5 up to and including 20, such as from and including 5 up to and including 10, such as from and including 5 up to and including 8, such as from and including 6 up to and including 20, such as from and including 6 up to and including 10, such as from and including 6 up to and including 8 (e.g., n equals 7).

[0326] and

[0327]

[0328] wherein each n in formula A2b is independently selected and each n in formula A2b is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 15, more preferably from and including 2 up to and including 12, most preferably from and including 2 up to and including 11, such as from and including 3 up to and including 20, such as from and including 3 up to and including 15, such as from and including 3 up to and including 12, such as from and including 3 up to and including 11, such as from and including 4 up to and including 20, such as from and including 4 up to and including 15, such as from and including 4 up to and including 12, such as from and including 4 up to and including 11, such as from and including 5 up to and including 20, such as from and including 5 up to and including 15, such as from and including 5 up to and including 12, such as from and including 5 up to and including 11, such as from and including 6 up to and including 20, such as from and including 6 up to and including 15, such as from and including 6 up to and including 12, such as from and including 6 up to and including 11, such as from and including 7 up to and including 20, such as from and including 7 up to and including 15, such as from and including 7 up to and including 12, such as from and including 7 up to and including 11, such as from and including 8 up to and including 20, such as from and including 8 up to and including 15, such as from and including 8 up to and including 12, such as from and including 8 up to and including 11, such as from and including 9 up to and including 20, such as from and including 9 up to and including 15, such as from and including 9 up to and including 12, such as from and including 9 up to and including 11, such as from and including 10 up to and including 20, such as from and including 10 up to and including 15, such as from and including 10 up to and including 12, such as from and including 10 up to and including 11 (e.g., n equals 11);

[0329] and

[0330]

[0331] Each n in formula A2c is independently selected, and each n in formula A2c is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 15, more preferably from and including 2 up to and including 12, most preferably from and including 2 up to and including 11, such as from and including 3 up to and including 20, such as from and including 3 up to and including 15, such as from and including 3 up to and including 12, such as from and including 3 up to and including 11, such as from and including 4 up to and including 20, such as from and including 4 up to and including 15, such as from and including 4 up to and including 12, such as from and including 4 up to and including 11, such as from and including 5 up to and including 20, such as from and including 5 up to and including 15, such as from and including 5 up to and including 12, such as from and including 5 up to and including 11, such as from and including 6 up to and including 20, such as from and including 6 up to and including 15, such as from and including 6 up to and including 12, such as from and including 6 up to and including 11, such as from and including 7 up to and including 20, such as from and including 7 up to and including 15, such as from and including 7 up to and including 12, such as from and including 7 up to and including 11, such as from and including 8 up to and including 20, such as from and including 8 up to and including 15, such as from and including 8 up to and including 12, such as from and including 8 up to and including 11, such as from and including 9 up to and including 20, such as from and including 9 up to and including 15, such as from and including 9 up to and including 12, such as from and including 9 up to and including 11, such as from and including 10 up to and including 20, such as from and including 10 up to and including 15, such as from and including 10 up to and including 12, such as from and including 10 up to and including 11 (e.g., n equals 11);

[0332] and

[0333]

[0334] and

[0335]

[0336] and

[0337] wherein

[0338] the AZ3 compound is selected from the group consisting of compounds having formula A3a

[0339]

[0340] Each n in formula A3a is independently selected, and each n in formula A3a is an integer ranging from and including 2 up to and including 20, preferably from and including 2 up to and including 15, more preferably from and including 2 up to and including 10, most preferably from and including 2 up to and including 9, such as from and including 2 up to and including 8, such as from and including 2 up to and including 7, such as from and including 2 up to and including 6, such as from and including 2 up to and including 5, such as from and including 2 up to and including 4, such as from and including 2 up to and including 3 (e.g., n equals 3, e.g., n equals 2);

[0341] and

[0342] wherein

[0343] the AZ5 compound is selected from the group consisting of: compounds having formula A5a

[0344]

[0345] Each n in formula A5a is independently selected, and each n in formula A5a is an integer ranging from and including 2 up to and including 40, preferably from and including 2 up to and including 30, more preferably from and including 2 up to and including 20, most preferably from and including 2 up to and including 10, such as from and including 2 up to and including 9, such as from and including 2 up to and including 8, such as from and including 2 up to and including 7, such as from and including 2 up to and including 6, such as from and including 2 up to and including 5, such as from and including 2 up to and including 4, such as from and including 3 up to and including 40, such as from and including 3 up to and including 30, such as from and including 3 up to and including 20, such as from and including 3 up to and including 10, such as from and including 3 up to and including 9, such as from and including 3 up to and including 8, such as from and including 3 up to and including 7, such as from and including 3 up to and including 6, such as from and including 3 up to and including 5, such as from and including 3 up to and including 4 (e.g., n equals 4, e.g., n equals 3).

[0346] Preferably, X1 and / or X2 and / or X3 and / or X4 and / or X5 do not contain any structural units of (or equivalently derived from) phenol formaldehyde resin (also known as phenolic resin); examples of phenol - formaldehyde (PF) resins include novolac resins (acid - catalyzed PF resins with a formaldehyde - to - phenol ratio equal to or less than 1) and resole resins (base - catalyzed PF resins with a formaldehyde - to - phenol ratio greater than 1, usually equal to 1.5).

[0347] Preferably, the AZ component is selected from the group consisting of: AZ1 compound, and wherein the AZ1 compound is a compound of the following formula,

[0348]

[0349] Preferably, the AZ component is selected from the group consisting of: AZ2 compounds, and wherein the AZ2 compound is a compound of the following formula,

[0350]

[0351] Preferably, the AZ component is selected from the group consisting of: AZ2 compounds, and wherein the AZ2 compound is a compound of the following formula,

[0352]

[0353] Preferably, the AZ component is selected from the group consisting of: AZ2 compounds, and wherein the AZ2 compound is a compound of the following formula,

[0354]

[0355] Preferably, the AZ1 compound and / or AZ2 compound and / or AZ3 compound and / or AZ4 compound and / or AZ5 compound comprises polyoxyethylene (-O-CH2-CH2-) x groups, and / or polyoxypropylene (-O-CHCH3-CH2-) x groups and / or polytetrahydrofuran (-O-CH2-CH2-CH2-CH2) x groups, preferably, the amount of the groups is at least 10 mol% and at most 92 mol%, more preferably at least 15 mol% and at most 85 mol%, even more preferably at least 25 mol% and at most 75 mol%, such as at least 30 mol% and at most 65 mol%, such as at least 35 mol% and at most 55 mol% relative to the corresponding AZ1 compound and / or AZ2 compound and / or AZ3 compound and / or AZ4 compound and / or AZ5 compound with respect to which these mol% are concerned.

[0356] Preferably, the AZ1 compound and / or AZ2 compound and / or AZ3 compound and / or AZ4 compound and / or AZ5 compound comprises methoxypoly(ethylene glycol) (MPEG) and / or poly(ethylene glycol) (PEG) groups (each of these groups having a calculated number-average molecular weight (M n)) Preferably, the amount of the group is at least 1 mol% and at most 35 mol%, more preferably at least 3 mol% and at most 30 mol%, even more preferably at least 5 mol% and at most 27 mol%, such as at least 7 mol% and at most 20 mol%, such as at least 8 mol% and at most 17 mol%, such as at least 9 mol% and at most 15 mol%, such as at least 10 mol% and at most 13 mol% relative to the corresponding AZ1 compound and / or AZ2 compound and / or AZ3 compound and / or AZ4 compound and / or AZ5 compound with respect to which these mol% are concerned.

[0357] The particles of the present invention may optionally (also) contain other components, such as pigments and / or waxes, and / or conventional (processing) additives, such as a degassing agent - if the particles are used in powder coatings, a leveling agent, an appearance enhancer or a (light) stabilizer. Suitable stabilizers include, for example, a primary antioxidant and / or a co-antioxidant and a UV stabilizer, such as quinones, (sterically hindered) phenolic compounds, phosphites, phosphonites, thioethers and HALS (hindered amine light stabilizers). Examples of suitable degassing agents include cyclohexanedimethanol dibenzoate, benzoin and benzoin derivatives, such as those described in WO 02 / 50194.

[0358] In yet another aspect, the present invention provides a cured form (crosslinked particles of the present invention) obtained by curing the particles of the present invention as disclosed in this specification. The curing of the particles of the present invention can be carried out by a chemical reaction (resulting in the formation of irreversible covalent chemical bonds) or a combination of physical drying and a chemical reaction. The curing of the particles of the present invention can be carried out under standard conditions (as defined in this specification), or by using heat, or by using pressure, or by applying a vacuum, or by radiation such as ultraviolet radiation, or by any combination thereof. Preferably, the particles are cured at a temperature of at least 0 °C and at most 85 °C, preferably at least 15 °C and at most 80 °C, more preferably at least 23 °C and at most 70 °C, most preferably at least 30 °C and at most 85 °C, such as at least 15 °C and at most 30 °C for a period of time that can vary and is preferably at most 60 minutes, more preferably at most 30 minutes, even more preferably at most 15 minutes.

[0359] The particles of the present invention can be cured in the presence of a cationic initiator.

[0360] Alternatively, the particles of the present invention can be cured under standard conditions, e.g., for 12 - 48 h (preferably 24 - 48 h), in the presence of a polymer (e.g., a polymer having an acid value in the range of 5 mg KOH / g to 300 mg KOH / g, preferably 8 mg KOH / g to 200 mg KOH / g, more preferably 10 mg KOH / g to 150 mg KOH / g as determined according to ASTM D1639 - 90(1996)e1, and wherein the polymer may optionally contain ionic functional groups), and / or by thermal curing at an elevated temperature (e.g., 70 - 80 °C) and atmospheric pressure for 10 - 60 minutes (preferably 15 - 30 minutes, more preferably 20 minutes), and / or by any combination of curing at room temperature and curing at an elevated temperature; an annealing step (e.g., 50 °C for 16 h) may also be included, especially between curing at an elevated temperature and atmospheric pressure and curing under standard conditions, where the annealing step follows curing at an elevated temperature and atmospheric pressure. Such mixtures of the present invention can preferably be cured at a temperature of at least 0 °C and at most 85 °C, preferably at least 15 °C and at most 80 °C, more preferably at least 23 °C and at most 70 °C, most preferably at least 30 °C and at most 85 °C, e.g., at least 15 °C and at most 30 °C, for a period of time that can vary and is preferably at most 60 minutes, more preferably at most 30 minutes, even more preferably at most 15 minutes.

[0361] Obviously, curing at an elevated temperature and atmospheric pressure requires a shorter curing time; curing can also be achieved by using pressure or by applying a vacuum, or by radiation (e.g., ultraviolet (UV) radiation), or by any combination thereof. Such polymers can be selected from the group consisting of: polyesters, polyamides, polycarbonates, polyimides, alkyd resins, urethane - modified alkyd resins (uralkyds), polyacrylics, polyurethanes, poly(urethane - acrylics), and mixtures thereof, preferably the polymers are selected from the group consisting of: polyamides, polyacrylics, polyurethanes, poly(urethane - acrylics), and mixtures thereof, most preferably the polymers are selected from the group consisting of: polyacrylics, polyurethanes, poly(urethane - acrylics), and mixtures thereof.

[0362] 2. Method for manufacturing the particles of the present invention

[0363] To prepare the particles of the present invention, the AZ component must first be prepared.

[0364] In principle, the (aziridinyl - hydroxy) - functional organic component (AZ component) as described in the present specification is preferably obtained by reacting an aziridine of formula AZIR (abbreviated as 'aziridine - AZIR') with at least one polyepoxide having at least two and at most six epoxy groups.

[0365]

[0366] Wherein

[0367] R1 is selected from the group consisting of hydrogen and methyl; and

[0368] R2 is selected from the group consisting of hydrogen, methyl and C2-C5 alkyl; and

[0369] R3 is selected from the group consisting of methyl and C2-C4 alkyl; and

[0370] R4 is selected from the group consisting of hydrogen, methyl and C2-C4 alkyl.

[0371] Exemplary aziridines of formula AZIR include, but are not limited to, propyleneimine, 1,2-dimethylaziridine, 2,2-dimethylaziridine, 2-ethylaziridine, butylaziridine.

[0372] More specifically, the AZ1 compounds (as described herein in the present specification) are preferably obtained by reacting an aziridine of formula AZIR with at least one polyepoxide having two epoxy groups. Exemplary polyepoxides having two epoxy groups include, but are not limited to, any glycidyl ether of a dihydroxy compound having a molecular weight of at least 374 Da, such as polypropylene glycol diglycidyl ether, e.g., GE-24 available from CVC Thermoset Specialties GE-24.

[0373] More specifically, the AZ2 compounds (as described herein in the present specification) are preferably obtained by reacting an aziridine of formula AZIR with at least one polyepoxide having three epoxy groups. Exemplary polyepoxides having three epoxy groups include, but are not limited to, any glycidyl ether of a trifunctional hydroxy compound having a molecular weight of at least 261 Da, and both GE-36 and GE-36 and 9000.

[0374] More specifically, the AZ3 compounds (as described herein in the present specification) are preferably obtained by reacting an aziridine of formula AZIR with at least one polyepoxide having four epoxy groups. Exemplary polyepoxides having four epoxy groups include, but are not limited to, any glycidyl ether of a tetrahydroxy compound having a molecular weight of at least 148 Da, such as, for example, ethoxylated pentaglycidyl ether, e.g., the polyol R4410 available from Perstop.

[0375] More specifically, the AZ4 compound (as described herein in this specification) is preferably obtained by reacting an aziridine of formula AZIR with at least one polyepoxide having five epoxy groups. Exemplary polyepoxides having five epoxy groups include, but are not limited to, any glycidyl ether of a pentahydroxy compound.

[0376] More specifically, the AZ5 compound (as described herein in this specification) is preferably obtained by reacting an aziridine of formula AZIR with at least one polyepoxide having six epoxy groups. Exemplary polyepoxides having six epoxy groups include, but are not limited to, any glycidyl ether of a hexahydroxy compound, such as the hexaglycidyl ether of dipentaerythritol.

[0377] The reaction (the term refers to and encompasses any and all reactions just mentioned above in this subsection) occurs at any temperature from 20 °C to 110 °C, more preferably from 50 °C to 95 °C, most preferably from 70 °C to 90 °C, and its progress can be monitored by 1 1H-NMR spectroscopy. The reaction proceeds as long as the epoxy groups react; this is monitored and verified by 1 1H-NMR spectroscopy, where the characteristic 1 1H-NMR chemical shift (2.5 - 3 ppm) of the epoxy protons disappears. Preferably, the reaction is carried out without a solvent. However, if desired (e.g., to reduce viscosity), one or more solvents, such as methanol, ethanol, toluene, can be used during or after the reaction. If a solvent is used, it is usually convenient to first dissolve the polyepoxide in the solvent (or solvent mixture) before adding the aziridine - AZIR to the reaction mixture. The molar ratio of the number of moles of the aziridine group of aziridine - AZIR to the number of moles of the epoxy groups of the polyepoxide is at least 1 and at most 8, more preferably at least 1 and at most 4, even more preferably at least 1.1 and at most 3, most preferably at least 1.2 and at most 2.2. Once the reaction is complete, the residual aziridine - AZIR is distilled off, preferably at a temperature of 60 °C to 90 °C, more preferably 65 °C to 80 °C and under reduced pressure, such as 20 mbar to 50 mbar, preferably 30 - 45 mbar. Preferably, once the reaction is complete, the residual aziridine - AZIR is distilled off under reduced pressure at 70 °C from 20 mbar to 50 mbar, more preferably at 70 °C from 30 mbar to 45 mbar. Subsequently, a further distillation step is carried out at 25 °C to 40 °C, at 2 mbar to 4 mbar to remove any unreacted aziridine - AZIR and any other volatiles, until by 1Aziridine-AZIR cannot be detected by H-NMR spectroscopy. It is usually useful to add an additional solvent to the reaction mixture before or during distillation to facilitate the removal of excess Aziridine-AZIR. If necessary, a base can be used during the reaction to reduce possible acid sources. The bases include both organic bases (such as tertiary amines) and inorganic bases (such as sodium carbonate or potassium carbonate or, for example, calcium hydroxide). The inorganic base can be filtered off after the reaction is complete.

[0378] For example, the AZ2 compound of formula A2d

[0379]

[0380] can be prepared by reacting 9000 (6.26 mmol) (available from CVC Thermoset Specialties) with propyleneimine (70.22 mmol) in the presence of potassium carbonate (250 mg) at 80 °C for 3 h.

[0381]

[0382] A highly excessive amount of propyleneimine is usually used to dissolve 9000 (the molar ratio of aziridine-AZIR to epoxy groups). The reaction can be monitored by 1 H-NMR. After 3 h at 80 °C, the chemical shift of the epoxy protons is not visible in 1 H-NMR; only some small peaks due to impurities are present. Once the reaction mixture has been left at 80 °C for 3 h to 22 h, 1 the H-NMR spectrum no longer changes. The reaction mixture is cooled to room temperature; the reaction mixture is diluted with toluene. The potassium carbonate is filtered off, and the excess propyleneimine is distilled off with toluene at 70 °C and 40 mbar. The residue is kept under reduced pressure at 90 - 95 °C and 3 - 4 mbar (oil pump) for 2 h to remove any residual propyleneimine and toluene. The reaction product solidifies rapidly upon cooling. 1 H-NMR does not show any peaks attributable to any residual propyleneimine.

[0383] In principle, in the method for manufacturing an AZ compound in which Y is a monovalent (aziridinyl hydroxycyclohexane) organic group of formula B2 or a monovalent (aziridinyl hydroxycyclohexane) organic group of formula B3, the AZ compound is preferably obtained by reacting hydroxycyclohexene oxide with the isocyanurate of a diisocyanate and then reacting with aziridine-AZIR (such as propyleneimine). For example, the AZ component in which Y is a monovalent (aziridinyl hydroxycyclohexane) organic group of formula B2 or a monovalent (aziridinyl hydroxycyclohexane) organic group of formula B3 can be prepared from 1-hydroxycyclohexene oxide (see the following formula)

[0384]

[0385] The 1-hydroxycyclohexene oxide is obtained by the peracetic acid epoxidation reaction of 1-hydroxycyclohexene. The 1-hydroxycyclohexene oxide is reacted with the isocyanurate of hexamethylene diisocyanate, and then reacted with 3-fold excess of propyleneimine at 80 °C for 24 h. Thereafter, the excess propyleneimine is distilled off under reduced pressure at a temperature of 50 °C. The molecular weight of the obtained AZ compound is 1018 Da.

[0386] Alternatively, a polyoxyalkylene containing at least one amino functional group (preferably a secondary amino functional group) or at least one carboxylic acid functional group is reacted with some of the epoxy groups of a polyepoxide, and then the polyepoxide is reacted with aziridine-AZIR, as described above. This can be a reaction scheme for introducing a polyether group into any one of X1 to X5.

[0387] Alternatively, aziridine-AZIR can be partially reacted with a polyoxyalkylene containing at least one carboxylic acid functional group, and then aziridine-AZIR is reacted with a polyepoxide, as described above. This can be a reaction scheme for introducing a polyether group into any one of X1 to X5.

[0388] Preferably, a mono-hydroxy or mono-amine functional polyether can be reacted with 2,4-toluene diisocyanate in a molar ratio of 1:1, and its reaction can subsequently be reacted with some of the hydroxyl groups formed after the reaction of the imine with the epoxide.

[0389] The particles can be obtained by a method comprising the following steps:

[0390] i) providing the aqueous dispersion of the present invention; and

[0391] ii) removing the water and any organic solvents present, if any, from the aqueous dispersion, preferably by spray drying or freeze drying or distillation under vacuum, to obtain the particles; and

[0392] iii) collecting the particles, and

[0393] iv) optionally further drying the particles; and

[0394] v) optionally applying means, such as grinding, which convert the collected particles into any form in which the solid material may exist under standard conditions.

[0395] (In the context of this specification, for the sake of brevity, this method is referred to as'method A').

[0396] The particles obtained by Method A can have a size, as determined by dynamic light scattering according to the specification, of at least 2 nm and at most 3000 nm, preferably at least 2 nm and at most 2500 nm, more preferably at least 2 nm and at most 2000 nm, even more preferably at least 2 nm and at most 1500 nm, for example at least 2 nm and at most 1000 nm, for example at least 2 nm and at most 900 nm, for example at least 2 nm and at most 800 nm, for example at least 2 nm and at most 600 nm, for example at least 2 nm and at most 500 nm, for example at least 2 nm and at most 400 nm, for example at least 2 nm and at most 350 nm, for example at least 2 nm and at most 300 nm, for example at least 10 nm and at most 3000 nm, for example at least 10 nm and at most 2500 nm, for example at least 10 nm and at most 2000 nm, for example at least 10 nm and at most 1500 nm, for example at least 10 nm and at most 1000 nm, for example at least 10 nm and at most 900 nm, for example at least 10 nm and at most 800 nm, for example at least 10 nm and at most 600 nm, for example at least 10 nm and at most 500 nm, for example at least 10 nm and at most 400 nm, for example at least 10 nm and at most 350 nm, for example at least 10 nm and at most 300 nm, for example at least 20 nm and at most 3000 nm, for example at least 20 nm and at most 2500 nm, for example at least 20 nm and at most 2000 nm, for example at least 20 nm and at most 1500 nm, for example at least 20 nm and at most 1000 nm, for example at least 20 nm and at most 900 nm, for example at least 20 nm and at most 800 nm, for example at least 20 nm and at most 600 nm, for example at least 20 nm and at most 500 nm, for example at least 20 nm and at most 400 nm, for example at least 20 nm and at most 350 nm, for example at least 20 nm and at most 300 nm, for example at least 30 nm and at most 3000 nm, for example at least 30 nm and at most 2500 nm, for example at least 30 nm and at most 2000 nm, for example at least 30 nm and at most 1500 nm, for example at least 30 nm and at most 1000 nm, for example at least 30 nm and at most 900 nm, for example at least 30 nm and at most 800 nm, for example at least 30 nm and at most 600 nm, for example at least 30 nm and at most 500 nm, for example at least 30 nm and at most 400 nm, for example at least 30 nm and at most 350 nm, for example at least 30 nm and at most 300 nm, for example at least 40 nm and at most 3000 nm, for example at least 40 nm and at most 2500 nm, for example at least 40 nm and at most 2000 nm, for example at least 40 nm and at most 1500 nm, for example at least 40 nm and at most 1000 nm, for example at least 40 nm and at most 900 nm, for example at least 40 nm and at most 800 nm, for example at least 40 nm and at most 600 nm,For example, at least 40 nm and at most 500 nm, for example, at least 40 nm and at most 400 nm, for example, at least 40 nm and at most 350 nm, for example, at least 40 nm and at most 300 nm, for example, at least 50 nm and at most 3000 nm, for example, at least 50 nm and at most 2500 nm, for example, at least 50 nm and at most 2000 nm, for example, at least 50 nm and at most 1500 nm, for example, at least 50 nm and at most 1000 nm, for example, at least 50 nm and at most 900 nm, for example, at least 50 nm and at most 800 nm, for example, at least 50 nm and at most 600 nm, for example, at least 50 nm and at most 500 nm, for example, at least 50 nm and at most 400 nm, for example, at least 50 nm and at most 350 nm, for example, at least 50 nm and at most 300 nm, for example, at least 60 nm and at most 3000 nm, for example, at least 60 nm and at most 2500 nm, for example, at least 60 nm and at most 2000 nm, for example, at least 60 nm and at most 1500 nm, for example, at least 60 nm and at most 1000 nm, for example, at least 60 nm and at most 900 nm, for example, at least 60 nm and at most 800 nm, for example, at least 60 nm and at most 600 nm, for example, at least 60 nm and at most 500 nm, for example, at least 60 nm and at most 400 nm, for example, at least 60 nm and at most 350 nm, for example, at least 60 nm and at most 300 nm, for example, at least 70 nm and at most 3000 nm, for example, at least 70 nm and at most 2500 nm, for example, at least 70 nm and at most 2000 nm, for example, at least 70 nm and at most 1500 nm, for example, at least 70 nm and at most 1000 nm, for example, at least 70 nm and at most 900 nm, for example, at least 70 nm and at most 800 nm, for example, at least 70 nm and at most 600 nm, for example, at least 70 nm and at most 500 nm, for example, at least 70 nm and at most 400 nm, for example, at least 70 nm and at most 350 nm, for example, at least 70 nm and at most 300 nm, for example, at least 80 nm and at most 3000 nm, for example, at least 80 nm and at most 2500 nm, for example, at least 80 nm and at most 2000 nm, for example, at least 80 nm and at most 1500 nm, for example, at least 80 nm and at most 1000 nm, for example, at least 80 nm and at most 900 nm, for example, at least 80 nm and at most 800 nm, for example, at least 80 nm and at most 600 nm, for example, at least 80 nm and at most 500 nm, for example, at least 80 nm and at most 400 nm, for example, at least 80 nm and at most 350 nm, for example, at least 80 nm and at most 300 nm, for example, at least 90 nm and at most 3000 nm, for example, at least 90 nm and at most 2500 nm, for example, at least 90 nm and at most 2000 nm, for example, at least 90 nm and at most 1500 nm, for example, at least 90 nm and at most 1000 nmFor example, an average hydrodynamic diameter (D, based on scattering intensity) of at least 90 nm and at most 900 nm, for example at least 90 nm and at most 800 nm, for example at least 90 nm and at most 600 nm, for example at least 90 nm and at most 500 nm, for example at least 90 nm and at most 400 nm, for example at least 90 nm and at most 350 nm, for example at least 90 nm and at most 300 nm, for example at least 100 nm and at most 3000 nm, for example at least 100 nm and at most 2500 nm, for example at least 100 nm and at most 2000 nm, for example at least 100 nm and at most 1500 nm, for example at least 100 nm and at most 1000 nm, for example at least 100 nm and at most 900 nm, for example at least 100 nm and at most 800 nm, for example at least 100 nm and at most 600 nm, for example at least 100 nm and at most 500 nm, for example at least 100 nm and at most 400 nm, for example at least 100 nm and at most 350 nm, for example at least 100 nm and at most 300 nm H )

[0397] The average hydrodynamic diameter (D, based on scattering intensity) of the particles can be controlled in a variety of ways H ). For example, during the preparation of the aqueous dispersion of the present invention (see Subsection 3, 'Aqueous dispersion of the present invention'), the D of the particles can be controlled by using different types and / or different amounts of dispersants, and / or by applying different shear stresses, and / or by applying different temperatures H . For example, the D of the particles H is inversely proportional to the amount of dispersant used in the preparation of the aqueous dispersion of the present invention; for example, the D of the particles H decreases by increasing the amount of dispersant. For example, the D of the particles H is inversely proportional to the shear stress applied during the preparation of the aqueous dispersion of the present invention; for example, the D of the particles H decreases by increasing the shear stress. Exemplary dispersants include, but are not limited to, ATLAS TM G-5000 and ATLAS TM G-5002L-LQ supplied by Croda

[0398] The particles of the present invention can be prepared by Method A

[0399] The particles of the present invention can be cured in the presence of a cationic initiator

[0400] Alternatively, the particles of the present invention can be cured under standard conditions for, e.g., 12 - 48 h (preferably 24 - 48 h) in the presence of a polymer (e.g., a polymer having an acid value in the range of 5 mg KOH / g to 300 mg KOH / g, preferably 8 mg KOH / g to 200 mg KOH / g, more preferably 10 mg KOH / g to 150 mg KOH / g as determined according to ASTM D1639 - 90(1996)e1, and wherein the polymer can optionally contain ionic functional groups), and / or by thermal curing at an elevated temperature (e.g., 70 - 80 °C) and atmospheric pressure for 10 - 60 minutes (preferably 15 - 30 minutes, more preferably 20 minutes), and / or by curing at room temperature in any combination with curing at an elevated temperature; an annealing step (e.g., 50 °C for 16 h) can also be included, especially between curing at an elevated temperature and atmospheric pressure and curing under standard conditions, wherein the annealing step follows curing at an elevated temperature and atmospheric pressure. Such mixtures of the present invention can preferably be cured at a temperature of at least 0 °C and at most 85 °C, preferably at least 15 °C and at most 80 °C, more preferably at least 23 °C and at most 70 °C, most preferably at least 30 °C and at most 85 °C, e.g., at least 15 °C and at most 30 °C, for a period of time that can vary and is preferably at most 60 minutes, more preferably at most 30 minutes, even more preferably at most 15 minutes.

[0401] Obviously, curing at an elevated temperature and atmospheric pressure requires a shorter curing time; curing can also be achieved by using pressure or by applying a vacuum, or by radiation (e.g., ultraviolet (UV) radiation), or by any combination thereof. Such polymers can be selected from the group consisting of: polyesters, polyamides, polycarbonates, polyimides, alkyd resins, urethane - modified alkyd resins (uralkyds), polyacrylics, polyurethanes, poly(urethane - acrylates), and mixtures thereof, preferably the polymers are selected from the group consisting of: polyamides, polyacrylics, polyurethanes, poly(urethane - acrylates), and mixtures thereof, most preferably the polymers are selected from the group consisting of: polyacrylics, polyurethanes, poly(urethane - acrylates), and mixtures thereof.

[0402] 3. Mixtures, aqueous dispersions, and aqueous compositions of the present invention

[0403] The mixtures, aqueous dispersions and aqueous compositions of the present invention are disclosed throughout the specification. As used in this specification, the term 'the mixture of the present invention' (or alternatively 'the present invention mixture') includes any and all of its preferred options, combinations of its features and ranges, and combinations of any and all of its preferred options with any and all combinations of its features and ranges. As used in this specification, the term 'the aqueous dispersion of the present invention' (or alternatively 'the present invention aqueous dispersion') includes any and all of its preferred options, combinations of its features and ranges, and combinations of any and all of its preferred options with any and all combinations of its features and ranges. As used in this specification, the term 'the aqueous composition of the present invention' (or alternatively 'the present invention aqueous composition') includes any and all of its preferred options, combinations of its features and ranges, and combinations of any and all of its preferred options with any and all combinations of its features and ranges. Thus, any and all of the present invention mixtures, present invention aqueous dispersions, aqueous compositions disclosed in this subsection 3, including any and all of their preferred items, combinations of their features and ranges, and combinations of any and all of their preferred items with any and all combinations of their features and ranges - throughout the specification - are collectively referred to as the present invention mixtures, present invention aqueous dispersions, aqueous compositions.

[0404] Mixture of the present invention

[0405] The present invention mixture is according to any one of A22 to A25 and as disclosed throughout the specification. More specifically, the present invention mixture comprises:

[0406] i) Particles of an (aziridinylhydroxy)-functional organic component according to any one of A1a or A1 to A21 or any combination derived from the disclosure of subsection 1 and / or subsection 3, and

[0407] ii) A polymer having an acid value of at least 5 mg KOH / g and at most 300 mg KOH / g, preferably at least 8 mg KOH / g and at most 200 mg KOH / g, more preferably at least 10 mg KOH / g and at most 150 mg KOH / g as determined according to ASTM D1639-90(1996)e1, and wherein the polymer may optionally contain ionic functional groups.

[0408] The mixture of the present invention can be solid, semi-solid or liquid under standard conditions. The mixture of the present invention can be prepared by mixing:

[0409] i) The particles of the present invention, and

[0410] ii) a polymer having an acid value determined according to ASTM D1639-90(1996)e1 in the range of 5 mg KOH / g to 300 mg KOH / g, preferably 8 mg KOH / g to 200 mg KOH / g, more preferably 10 mg KOH / g to 150 mg KOH / g, and wherein the polymer may optionally contain ionic functional groups.

[0411] The mixing of components i) and ii) can be carried out under standard conditions in the presence of water and / or an organic solvent to obtain a liquid mixture. Alternatively, the mixing can be carried out by directly mixing components i) and ii) under standard conditions.

[0412] Preferably, the polymer is selected from the group consisting of: polyesters, polyamides, polycarbonates, polyimides, alkyd resins, urethane-modified alkyd resins (uralkyds), polyacrylics, polyurethanes, poly(urethane-acrylics), and mixtures thereof; preferably, the polymer is selected from the group consisting of: polyamides, polyacrylics, polyurethanes, poly(urethane-acrylics), and mixtures thereof; most preferably, the polymer is selected from the group consisting of: polyacrylics, polyurethanes, poly(urethane-acrylics), and mixtures thereof.

[0413] Preferably, based on the total weight of the aqueous composition, the polymer is present in an amount of at least 5% by weight and at most 65% by weight, preferably at least 10% by weight and at most 60% by weight, more preferably at least 20% by weight and at most 55% by weight, for example at least 30% by weight and at most 50% by weight, and wherein the total amount of all components constituting the mixture totals 100% by weight.

[0414] Preferably, the particles are present in an amount of at least 10% by weight and at most 100% by weight, preferably at least 15% by weight and at most 95% by weight, more preferably at least 20% by weight and at most 90% by weight, for example at least 25% by weight and at most 85% by weight, for example at least 30% by weight and at most 80% by weight, for example at least 35% by weight and at most 75% by weight, for example at least 40% by weight and at most 70% by weight, for example at least 40% by weight and at most 65% by weight, for example at least 40% by weight and at most 60% by weight, and wherein the total amount of all components constituting the mixture totals 100% by weight.

[0415] The particles of the present invention can be cured under standard conditions, for example, for 12 - 48 h (preferably 24 - 48 h), and / or by thermal curing at an elevated temperature (e.g., 70 - 80 °C) and atmospheric pressure for 10 - 60 minutes (preferably 15 - 30 minutes, more preferably 20 minutes), and / or any combination of curing at room temperature and curing at an elevated temperature; an annealing step (e.g., 50 °C for 16 h) can also be included, especially between curing at an elevated temperature and atmospheric pressure and curing under standard conditions, where the annealing step is after curing at an elevated temperature and atmospheric pressure. Such mixtures of the present invention can preferably be cured at a temperature of at least 0 °C and at most 85 °C, preferably at least 15 °C and at most 80 °C, more preferably at least 23 °C and at most 70 °C, most preferably at least 30 °C and at most 85 °C, for example, at least 15 °C and at most 30 °C, for a period of time that can vary and is preferably at most 60 minutes, more preferably at most 30 minutes, even more preferably at most 15 minutes.

[0416] Obviously, curing at an elevated temperature and atmospheric pressure requires a shorter curing time; curing can also be achieved by using pressure or by applying a vacuum, or by radiation (e.g., ultraviolet (UV) radiation), or by any combination thereof.

[0417] The mixtures of the present invention can optionally (also) contain other components, such as pigments and / or waxes, and / or conventional (processing) additives, such as degassing agents - if the particles are used in powder coatings, smoothing agents, appearance enhancers, or (light) stabilizers. Suitable stabilizers include, for example, primary antioxidants and / or co-antioxidants and UV stabilizers, such as quinones, (sterically hindered) phenolic compounds, phosphites, phosphonites, thioethers, and HALS (hindered amine light stabilizers). Examples of suitable degassing agents include cyclohexanedimethanol dibenzoate, benzoin.

[0418] Aqueous dispersion of the present invention

[0419] The aqueous dispersions of the present invention are according to any one of A26 to A34 and as disclosed throughout the specification. More specifically, the aqueous dispersions of the present invention have a pH of at least 7.5 and at most 14.0, preferably at least 8.0 and at most 14.0, for example, at least 8.5 and at most 13.5, for example, at least 9.0 and at most 13.0, for example, at least 9.2 and at most 12.5, for example, at least 9.4 and at most 12.0, for example, at least 9.6 and at most 11.6, for example, at least 10.5 and at most 11.5, as determined according to ISO 976:2013 and according to the specification, and wherein the aqueous dispersion comprises:

[0420] i) water, and

[0421] ii) The particles as disclosed in this specification are dispersed in the water.

[0422] Preferably, based on the total weight of the aqueous dispersion, the water is present in an amount of at least 30% by weight and at most 95% by weight, preferably at least 45% by weight and at most 85% by weight, such as at least 50% by weight and at most 70% by weight, such as at least 55% by weight and at most 65% by weight, and the total amount of all components constituting the aqueous dispersion totals 100% by weight.

[0423] Preferably, the aqueous dispersion of the present invention further contains an organic solvent in an amount of at most 40% by weight, preferably at most 30% by weight, such as at most 25% by weight, such as at most 20% by weight, such as at most 12% by weight, such as at most 10% by weight, such as at most 8% by weight, such as at most 5% by weight, such as at most 4% by weight, such as at most 3% by weight, such as at most 2% by weight, such as at most 1% by weight, such as at most 0.5% by weight, such as at most 0.2% by weight, such as at most 0.1% by weight, based on the total weight of the aqueous dispersion.

[0424] Preferably, the aqueous dispersion of the present invention does not contain an organic solvent.

[0425] Preferably, based on the total weight of the aqueous dispersion, the particles are present in an amount of at least 5% by weight and at most 70% by weight, preferably at least 10% by weight and at most 60% by weight, more preferably at least 20% by weight and at most 55% by weight, such as at least 25% by weight and at most 55% by weight, such as at least 30% by weight and at most 55% by weight, such as at least 35% by weight and at most 55% by weight, such as at least 35% by weight and at most 50% by weight, such as at least 35% by weight and at most 45% by weight, and the total amount of all components constituting the aqueous dispersion totals 100% by weight.

[0426] Preferably, the aqueous dispersion of the present invention contains a component T selected from the group consisting of: i) an organic compound having a molecular weight of less than 600 Da as determined by MALDI-TOF MS according to the specification and containing at least one aziridine ring, and ii) mixtures thereof. Based on the total weight of the AZ compound, the amount of the component T as determined by LC-MS according to the specification is at most 5% by weight, preferably at most 4% by weight, more preferably at most 3% by weight, such as at most 2% by weight, such as at most 1% by weight, such as at most 0.5% by weight, such as at most 0.1% by weight, such as at most 0.05% by weight.

[0427] Preferably, the aqueous dispersion of the present invention does not contain the component T.

[0428] Preferably, in the aqueous dispersion of the present invention, based on the total weight of the aqueous dispersion, the amount of chloride determined according to ASTM D1726-11 (2019) is at most 0.3% by weight, preferably at most 0.2% by weight, more preferably at most 0.1% by weight, such as at most 0.05% by weight, such as at most 0.03% by weight.

[0429] Preferably, the aqueous dispersion of the present invention is an aqueous coating dispersion.

[0430] The aqueous dispersion of the present invention can be prepared in several ways. For example, one method involves preparing the AZ component in a solvent; after purification (e.g., by distilling off excess aziridine - AZIR), the AZ component is introduced into water, in which optional surfactants / dispersants, surface tension modifiers, defoamers, solvents, thickeners, and / or any other additives may also be present. The AZ component can be introduced into water by using at least one surfactant (preferably at least one non - ionic surfactant) and adding the AZ component to water under good mixing. Generally, a high - shear mixer is most suitable for this method to ensure thorough mixing. If desired and if present, the solvent can be partially or completely distilled off. It is preferred to use a base during this method to ensure good retention of the aziridine groups. Preferably, part or all of the base (intended to be used) is added to the AZ component before dispersion into water. Preferably, a volatile organic base is added to the AZ component and an inorganic base is added to the water, and then the AZ component is introduced into the water. Alternatively and often preferably, water in which optional surfactants / dispersants, surface tension modifiers, defoamers, solvents, thickeners, and / or any other additives may also be present is slowly added to the AZ component, and after phase inversion, the mixture is further diluted with water to obtain the aqueous dispersion of the present invention. Preferably, the pH of the aqueous composition of the present invention thus prepared should be at least 7.5 and at most 14.0, preferably at least 8.0 and at most 14.0, such as at least 8.5 and at most 13.5, such as at least 9.0 and at most 13.0, such as at least 9.2 and at most 12.5, such as at least 9.4 and at most 12.0, such as at least 9.6 and at most 11.6. To achieve this, it is preferred that the pH can be adjusted with a base, preferably an inorganic base or an organic base. The aqueous dispersion of the present invention preferably contains ammonia, and / or secondary amines, and / or tertiary amines, and / or LiOH, and / or NaOH and / or KOH to adjust the pH to the desired value. Preferred amines are ammonia, dimethylethanolamine, diisopropylamine, isopropanolamine, diethylethanolamine, N,N - dimethylisopropanolamine, 3 - dimethylamino - 1 - propanol, 2 - [2 - (dimethylamino)ethoxy]ethanol, N - ethylmorpholine, dimethylbenzylamine, and triethylamine. Examples of the preparation of the aqueous dispersion of the present invention are shown in the examples.

[0431] The aqueous dispersion of the present invention can be obtained by a method comprising the following steps:

[0432] a) Mixing the AZ component - as disclosed throughout the specification - with an organic solvent to obtain mixture A; and

[0433] b) Mixing the AZ component - as disclosed throughout the specification - or mixture A with a dispersant to obtain mixture B; and

[0434] c) Mixing water and a base, or an alkaline aqueous medium with mixture B to obtain mixture C; and

[0435] d) Optionally (but preferably) removing the organic solvent from mixture C to obtain mixture D, and optionally mixing additional water or an alkaline aqueous medium into mixture D to obtain an aqueous dispersion of the AZ component.

[0436] Obviously, the particles of the present invention (which form part of the aqueous dispersion of the present invention) can be prepared by the method mentioned above.

[0437] The aqueous dispersion of the present invention can be cured under standard conditions for, for example, 12 - 48 h (preferably 24 - 48 h), and / or by thermal curing at an elevated temperature (e.g., 70 - 80 °C) and atmospheric pressure for 10 - 60 minutes (preferably 15 - 30 minutes, more preferably 20 minutes), and / or any combination of curing at room temperature and curing at an elevated temperature; an annealing step (e.g., 50 °C for 16 h) can also be included, especially between curing at an elevated temperature and atmospheric pressure and curing under standard conditions, where the annealing step follows curing at an elevated temperature and atmospheric pressure. Such mixtures of the present invention can preferably be cured at a temperature of at least 0 °C and at most 85 °C, preferably at least 15 °C and at most 80 °C, more preferably at least 23 °C and at most 70 °C, most preferably at least 30 °C and at most 85 °C, e.g., at least 15 °C and at most 30 °C, for a period of time that can vary and is preferably at most 60 minutes, more preferably at most 30 minutes, even more preferably at most 15 minutes.

[0438] Obviously, curing at elevated temperatures and atmospheric pressure requires a shorter curing time; curing can also be achieved by using pressure or by applying a vacuum, or by radiation (such as ultraviolet (UV) radiation), or by any combination thereof. Such polymers may be selected from the group consisting of: polyesters, polyamides, polycarbonates, polyimides, alkyd resins, urethane-modified alkyd resins (uralkyds), polyacrylics, polyurethanes, poly(urethane-acrylics), and mixtures thereof, preferably the polymers are selected from the group consisting of: polyamides, polyacrylics, polyurethanes, poly(urethane-acrylics), and mixtures thereof, most preferably the polymers are selected from the group consisting of: polyacrylics, polyurethanes, poly(urethane-acrylics), and mixtures thereof.

[0439] The aqueous dispersions of the present invention may optionally (also) contain other components, such as pigments and / or waxes, and / or conventional (processing) additives, such as degassing agents - if the particles are used in powder coatings, leveling agents, appearance enhancers, or (light) stabilizers. Suitable stabilizers include, for example, primary antioxidants and / or co-antioxidants and UV stabilizers, such as quinones, (sterically hindered) phenolic compounds, phosphites, phosphonites, thioethers, and HALS (hindered amine light stabilizers). Examples of suitable degassing agents include cyclohexanedimethanol dibenzoate, benzoin.

[0440] Aqueous composition of the present invention

[0441] The aqueous compositions of the present invention are according to any one of A37 to A44 and as disclosed throughout the specification. More specifically, the aqueous compositions of the present invention comprise:

[0442] i) an aqueous dispersion according to any one of A26 to A34, and

[0443] ii) a polymer having an acid value in the range of 5 mg KOH / g to 300 mg KOH / g, preferably 8 mg KOH / g to 200 mg KOH / g, more preferably 10 mg KOH / g to 150 mg KOH / g as determined according to ASTM D1639-90(1996)e1, and wherein the polymer may optionally contain ionic functional groups.

[0444] Preferably, the pH of the aqueous composition is at least 7.5 and at most 14.0, preferably at least 8.0 and at most 14.0, such as at least 8.5 and at most 13.5, such as at least 9.0 and at most 13.0, such as at least 9.2 and at most 12.5, such as at least 9.4 and at most 12.0, such as at least 9.6 and at most 11.6.

[0445] Preferably, the polymer is selected from the group consisting of: polyesters, polyamides, polycarbonates, polyimides, alkyd resins, urethane-modified alkyd resins (uralkyds), polyacrylics, polyurethanes, poly(urethane-acrylics), and mixtures thereof; preferably, the polymer is selected from the group consisting of: polyamides, polyacrylics, polyurethanes, poly(urethane-acrylics), and mixtures thereof; most preferably, the polymer is selected from the group consisting of: polyacrylics, polyurethanes, poly(urethane-acrylics), and mixtures thereof.

[0446] Preferably, the aqueous composition of the present invention further comprises up to 35% by weight, preferably up to 30% by weight, such as up to 25% by weight, such as up to 20% by weight, such as up to 15% by weight, such as up to 12% by weight, such as up to 10% by weight, such as up to 8% by weight, such as up to 5% by weight, such as up to 4% by weight, such as up to 3% by weight, such as up to 2% by weight, such as up to 1% by weight, such as up to 0.5% by weight, such as up to 0.2% by weight, such as up to 0.1% by weight of an organic solvent, based on the total weight of the aqueous composition.

[0447] Preferably, the aqueous dispersion is present in the aqueous composition in an amount of at least 0.1% by weight and at most 50% by weight, preferably at least 0.2% by weight and at most 45% by weight, more preferably at least 0.3% by weight and at most 40% by weight, such as at least 0.4% by weight and at most 35% by weight, such as at least 0.5% by weight and at most 30% by weight, such as at least 0.6% by weight and at most 25% by weight, such as at least 0.7% by weight and at most 20% by weight, such as at least 0.8% by weight and at most 15% by weight, such as at least 0.9% by weight and at most 12% by weight, such as at least 1% by weight and at most 10% by weight, such as at least 1.2% by weight and at most 8% by weight, such as at least 0.3% by weight and at most 25% by weight, such as at least 0.8% by weight and at most 15% by weight, such as at least 1.5% by weight and at most 12% by weight, such as at least 2.5% by weight and at most 10% by weight, such as at least 3% by weight and at most 8% by weight, based on the total weight of the aqueous composition of the present invention, and wherein the total amount of all components constituting the aqueous composition totals 100% by weight.

[0448] Preferably, the polymer is present in the aqueous composition in an amount of at least 5% by weight and at most 65% by weight, preferably at least 10% by weight and at most 60% by weight, more preferably at least 20% by weight and at most 55% by weight, such as at least 30% by weight and at most 50% by weight, based on the total weight of the aqueous composition of the present invention, and wherein the total amount of all components constituting the aqueous composition totals 100% by weight.

[0449] Preferably, the aqueous composition of the present invention does not contain organic solvents.

[0450] Preferably, the aqueous composition of the present invention is a coating composition, more preferably an aqueous coating composition.

[0451] The aqueous composition of the present invention can be prepared by mixing the aqueous dispersion of the present invention with an aqueous dispersion of a polymer. Preferably, this can be accomplished by slowly adding and mixing the aqueous dispersion of the present invention into the aqueous dispersion of the polymer. Alternatively, the aqueous dispersion of the polymer can be slowly added and mixed into the aqueous dispersion of the present invention, or an in-line mixing device can be used to mix them. Preferably, the aqueous dispersion of the present invention contains a surfactant (preferably a nonionic surfactant) to facilitate and enable thorough mixing with the aqueous dispersion of the polymer. Preferably, the pH of the aqueous composition of the present invention thus prepared should be at least 7.5 and at most 14.0, preferably at least 8.0 and at most 14.0, such as at least 8.5 and at most 13.5, such as at least 9.0 and at most 13.0, such as at least 9.2 and at most 12.5, such as at least 9.4 and at most 12.0, such as at least 9.6 and at most 11.6. To achieve this, preferably the pH of the aqueous dispersion of the present invention is at least 7.5 and at most 14.0, preferably at least 8.0 and at most 14.0, such as at least 8.5 and at most 13.5, such as at least 9.0 and at most 13.0, such as at least 9.2 and at most 12.5, such as at least 9.4 and at most 12.0, such as at least 9.6 and at most 11.6, such as at least 10.5 and at most 11.5, and the pH of the aqueous dispersion of the polymer is at least 7.5 and at most 14.0, preferably at least 8.0 and at most 14.0, such as at least 8.5 and at most 13.5, such as at least 9.0 and at most 13.0, such as at least 9.2 and at most 12.5, such as at least 9.4 and at most 12.0, such as at least 9.6 and at most 11.6. Preferably, the polymer suitable for preparing the aqueous mixture of the present invention is a polymer having an acid value in the range of 5 mg KOH / g to 300 mg KOH / g, preferably 8 mg KOH / g to 200 mg KOH / g, more preferably 10 mg KOH / g to 150 mg KOH / g as determined according to ASTM D1639-90(1996)e1, and wherein the polymer may optionally contain ionic functional groups; more preferably the polymer may be selected from the group consisting of: polyester, polyamide, polycarbonate, polyimide, alkyd resin, urethane-modified alkyd resin (uralkyds), polyacrylic acid, polyurethane, poly(urethane-acrylic acid), and mixtures thereof, preferably the polymer is selected from the group consisting of: polyamide, polyacrylic acid, polyurethane, poly(urethane-acrylic acid), and mixtures thereof, most preferably the polymer is selected from the group consisting of: polyacrylic acid, polyurethane, poly(urethane-acrylic acid), and mixtures thereof,

[0452] For example, an aqueous dispersion of poly(acrylate-methacrylate) suitable for preparing the aqueous composition of the present invention can be prepared as follows: Charge sodium dodecyl sulfate (30% solids in water, 18.6 grams of solution) and demineralized water (711 grams) into a 2 L four-necked flask equipped with a thermometer and an overhead stirrer. Place the reactor phase under a N2 atmosphere and heat to 82 °C. A mixture of i) demineralized water (112 grams), ii) sodium dodecyl sulfate (30% solids in water, 37.2 grams of solution), iii) methyl methacrylate (174.41 grams), iv) n-butyl acrylate (488.44 grams), and v) methacrylic acid (34.88 grams) is placed in a large feed funnel and emulsified with an overhead stirrer (monomer feed). Ammonium persulfate (1.75 grams) is dissolved in demineralized water (89.61 grams) and placed in a small feed funnel (initiator feed). Ammonium persulfate (1.75 grams) is dissolved in demineralized water (10.5 grams), and this solution is added to the reactor phase. Immediately thereafter, 5 vol% of the monomer feed is added to the reactor phase. Then, the reaction mixture is exothermed to 85 °C and held at 85 °C for 5 minutes. Then, the remaining monomer feed and initiator feed are fed into the reaction mixture over 90 minutes while maintaining the temperature at 85 °C. After the feeding is complete, the monomer feed funnel is rinsed with demineralized water (18.9 grams), and the reaction temperature is maintained at 85 °C for 45 minutes. Subsequently, the mixture is cooled to room temperature, adjusted to pH = 7.5 with an ammonia solution (6.25 wt% in demineralized water), and adjusted to 40% solids with additional demineralized water added.

[0453] The aqueous composition of the present invention can be obtained by a method comprising the following steps:

[0454] a) Mix the AZ component - as disclosed throughout the specification - with an organic solvent to obtain mixture A; and

[0455] b) Mix the AZ component - as disclosed throughout the specification - or mixture A with a dispersant to obtain mixture B; and

[0456] c) Mix water and a base, or an alkaline aqueous medium with mixture B to obtain mixture C; and

[0457] d) Optionally (but preferably) remove the organic solvent from mixture C to obtain mixture D, and optionally mix additional water or an alkaline aqueous medium into mixture D to obtain an aqueous dispersion of the AZ component, and

[0458] e) Mix the aqueous dispersion of the AZ component with an aqueous dispersion of a polymer (wherein the polymer is as disclosed in this subsection and subsections) to obtain the aqueous composition of the present invention.

[0459] The aqueous composition of the present invention can be cured under standard conditions for, for example, 12 - 48 h (preferably 24 - 48 h), and / or by thermal curing at an elevated temperature (e.g., 70 - 80 °C) and atmospheric pressure for 10 - 60 minutes (preferably 15 - 30 minutes, more preferably 20 minutes), and / or any combination of curing at room temperature and curing at an elevated temperature; an annealing step (e.g., 50 °C for 16 h) can also be included, especially between curing at an elevated temperature and atmospheric pressure and curing under standard conditions, where the annealing step follows curing at an elevated temperature and atmospheric pressure. Such aqueous compositions of the present invention can preferably be cured at a temperature of at least 0 °C and at most 85 °C, preferably at least 15 °C and at most 80 °C, more preferably at least 23 °C and at most 70 °C, most preferably at least 30 °C and at most 85 °C, for example at least 15 °C and at most 30 °C, for a period of time that can vary and is preferably at most 60 minutes, more preferably at most 30 minutes, even more preferably at most 15 minutes.

[0460] Obviously, curing at an elevated temperature and atmospheric pressure requires a shorter curing time; curing can also be achieved by using pressure or by applying a vacuum, or by radiation (e.g., ultraviolet (UV) radiation), or by any combination thereof.

[0461] The aqueous composition of the present invention can optionally (also) contain other components, such as pigments and / or waxes, and / or conventional (processing) additives, such as a degassing agent - if particles are used in powder coatings, a leveling agent, an appearance enhancer, or a (light) stabilizer. Suitable stabilizers include, for example, a primary antioxidant and / or a co - antioxidant and a UV stabilizer, such as quinones, (sterically hindered) phenolic compounds, phosphites, phosphonites, thioethers, and HALS (hindered amine light stabilizers). Examples of suitable degassing agents include cyclohexanedimethanol dibenzoate, benzoin.

[0462] 4. Other aspects and embodiments of the present invention

[0463] In yet another aspect, the present invention provides a kit of parts, the kit of parts comprising parts A and B that are physically separated from each other, wherein:

[0464] i) part A contains an aqueous dispersion according to any one of A26 to A34 or any combination derived from the disclosures in Section 1 and Section 3 and as disclosed throughout the specification, and

[0465] ii) Component B contains a polymer having an acid value, as determined according to ASTM D1639-90(1996)e1, in the range of 5 mg KOH / g to 300 mg KOH / g, preferably 8 mg KOH / g to 200 mg KOH / g, more preferably 10 mg KOH / g to 150 mg KOH / g, and wherein said polymer may optionally contain ionic functional groups, and wherein said polymer is preferably selected from the group consisting of: polyester, polyamide, polycarbonate, polyimide, alkyd resin, urethane-modified alkyd resin (uralkyds), polyacrylic acid, polyurethane, poly(urethane-acrylic acid), and mixtures thereof, more preferably said polymer is selected from the group consisting of: polyamide, polyacrylic acid, polyurethane, poly(urethane-acrylic acid), and mixtures thereof, most preferably said polymer is selected from the group consisting of: polyacrylic acid, polyurethane, poly(urethane-acrylic acid), and mixtures thereof,

[0466] wherein said Component A does not contain said polymer of Component B, and said Component B does not contain said aqueous dispersion of Component A.

[0467] In yet another aspect, the present invention provides a cured form of a particle according to any one of A1a or A1 to A22 or any combination derived from the disclosures in Sections 1 and 3 and as disclosed throughout the specification; preferably, said cured form is a film.

[0468] In yet another aspect, the present invention provides a cured form of a mixture according to any one of A22 to A25 or any combination derived from the disclosures in Sections 1 and 3 and as disclosed throughout the specification; preferably, said cured form is a film.

[0469] In yet another aspect, the present invention provides a cured form of an aqueous dispersion according to any one of A26 to A34 or any combination derived from the disclosures in Sections 1 and 3 and as disclosed throughout the specification; preferably, said cured form is a film.

[0470] In yet another aspect, the present invention provides a cured form of a particle according to any one of A35 to A36 or any combination derived from the disclosures in Sections 1 and 3 and as disclosed throughout the specification; preferably, said cured form is a film.

[0471] In yet another aspect, the present invention provides a cured form of an aqueous composition according to any one of A37 to A45 or any combination derived from the disclosures in Sections 1 and 3 and as disclosed throughout the specification; preferably, said cured form is a film.

[0472] In yet another aspect, the present invention provides an article comprising: i) particles according to any one of A1a or A1 to A21 or any combination derived from the disclosure in Subsection 1 and as disclosed throughout the specification, and / or ii) a mixture according to any one of A22 to A25 or any combination derived from the disclosure in Subsection 1 and Subsection 3 and as disclosed throughout the specification, and / or iii) an aqueous dispersion according to any one of A26 to A34 or any combination derived from the disclosure in Subsection 1 and Subsection 3 and as disclosed throughout the specification, and / or iv) particles according to any one of A35 to A36 or any combination derived from the disclosure in Subsection 1 and Subsection 3 and as disclosed throughout the specification, and / or v) an aqueous composition according to any one of A37 to A45 or any combination derived from the disclosure in Subsection 1 and Subsection 3 and as disclosed throughout the specification, and / or vi) a cured form according to any one of A46 to A51 or any combination derived from the disclosure in Subsection 1 and Subsection 3 and as disclosed throughout the specification; preferably, the article is selected from the group consisting of: textiles, glass, metal, composites, plastics, wood, engineered wood, wood imitation, leather, artificial leather, paper, fibers.

[0473] In yet another aspect, the present invention provides the use of any one or any combination of the following substances as a crosslinking agent:

[0474] i) particles according to any one of A1a or A1 to A21 or any combination derived from the disclosure in Subsection 1 and as disclosed throughout the specification;

[0475] ii) a mixture according to any one of A22 to A25 or any combination derived from the disclosure in Subsection 1 and Subsection 3 and as disclosed throughout the specification;

[0476] iii) an aqueous dispersion according to any one of A26 to A34 or any combination derived from the disclosure in Subsection 1 and Subsection 3 and as disclosed throughout the specification;

[0477] iv) particles according to any one of A35 to A36 or any combination derived from the disclosure in Subsection 1 and Subsection 3 and as disclosed throughout the specification;

[0478] v) an aqueous composition according to any one of A37 to A45 or any combination derived from the disclosure in Subsection 1 and Subsection 3 and as disclosed throughout the specification.

[0479] In yet another aspect, the present invention provides the use of any one or any combination of the following substances in coatings, paints, inks, varnishes, lubricants, adhesives, additive manufacturing, 3D printing, textiles, waxes, fuels, photography, plastics, medical compositions, medical devices:

[0480] i) Particles according to any one of A1a or A1 to A21 or any combination derived from the disclosure in Section 1 and as disclosed throughout the specification;

[0481] ii) Mixtures according to any one of A22 to A25 or any combination derived from the disclosure in Section 1 and Section 3 and as disclosed throughout the specification;

[0482] iii) Aqueous dispersions according to any one of A26 to A34 or any combination derived from the disclosure in Section 1 and Section 3 and as disclosed throughout the specification;

[0483] iv) Particles according to any one of A35 to A36 or any combination derived from the disclosure in Section 1 and Section 3 and as disclosed throughout the specification;

[0484] v) Aqueous compositions according to any one of A37 to A45 or any combination derived from the disclosure in Section 1 and Section 3 and as disclosed throughout the specification

[0485] vi) Kits of parts according to A45 or any combination derived from the disclosure in Section 1 and Section 3 and as disclosed throughout the specification;

[0486] vii) Cured forms according to any one of A46 to A47 or any combination derived from the disclosure in Section 1 and Section 3 and as disclosed throughout the specification;

[0487] viii) Articles according to any one of A52 to A53 or any combination derived from the disclosure in Section 1 and Section 3 and as disclosed throughout the specification.

[0488] Furthermore, another aspect of the present invention is any one of the particles shown in the embodiments of the present invention (Embodiment 1, Embodiment 2, Embodiment 3, Embodiment 4, Embodiment 5 and Embodiment 6).

[0489] Furthermore, another aspect of the present invention is any one of the liquid compositions shown in the embodiments of the present invention (Embodiment 1, Embodiment 2, Embodiment 3, Embodiment 4, Embodiment 5 and Embodiment 6).

[0490] In addition, another aspect of the present invention is any one of the aqueous dispersions shown in the embodiments (Embodiment 1, Embodiment 2, Embodiment 3, Embodiment 4, Embodiment 5, and Embodiment 6) according to the present invention.

[0491] Many other variations and embodiments of the present invention will be apparent to those skilled in the art, and such variations are within the scope of the claims.

[0492] Any features, elements, components, embodiments, ranges, and in particular any preferred features, preferred elements, preferred embodiments, preferred ranges, combinations of preferred ranges, and preferred options described throughout the specification may be combined with each other.

[0493] Other aspects of the present invention and their preferred features are given in the claims and the specification.

[0494] The present invention will now be described in detail by reference to the following illustrative and non-limiting embodiments. Examples

[0495] The present invention is explained in more detail with reference to the following non-limiting examples.

[0496] Unless otherwise explicitly stated, all examples shown in this subsection were carried out in a controlled laboratory environment under standard conditions (as defined in this specification), at a relative humidity of 50 ± 1% and an air flow of ≤ 0.1 m / s.

[0497] 1.1 Chemicals, Raw Materials, and Other Materials

[0498] Triethylamine (purity 99.7%) was supplied by ARKEMA. Propyleneimine (purity ≥ 99.0%) was supplied by Menadiona. Anhydrous potassium carbonate (K2CO3; purity ≥ 99.0%) was supplied by Alfa Aesar. Trimethylolpropane tris(2-methyl-1-aziridinepropionate) (CAS No. 64265-57-2; see the structure in Example 1C) was supplied by DSM (trade name 'Crosslinker CX-100'). B-300 is a methacrylic copolymer of methyl methacrylate (MMA) and butyl methacrylate (BMA) (acid value less than 1 mg KOH / g,

[0499] T g : 45 °C, theoretical molecular weight 16000 Da, density at 20 °C: 1.14 g / cm 3 , viscosity at 25 °C (40 wt% solution in 1,6-hexanediol diacrylate (HDDA)): 0.8 - 1.0 Pa·s; form at 25 °C: white solid), supplied by DSM.

[0500] N 3600 is an aliphatic polyisocyanate (trimer) with low viscosity based on hexamethylene diisocyanate (HDI) (NCO content: 23.0 ± 0.5% (M105 - ISO 11909); viscosity at 23 °C: 1200 ± 300 mPa·s (M014 - ISO 3219 / A.3); color value (Hazen): ≤ 40 (M017 - EN 1557); monomeric HDI: ≤ 0.25% (M106 - ISO 10283); equivalent weight: approximately 183; flash point: approximately 159 °C (DIN 53213 / 1); density at 20 °C: approximately 1.16 g / ml (DIN EN ISO 2811), supplied by Covestro. N 3900 is an aliphatic polyisocyanate with low viscosity based on hexamethylene diisocyanate (HDI) (NCO content: 23.0 ± 0.5% (M105 - ISO 11909); viscosity at 23 °C: 730 ± 100 mPa·s (M014 - ISO 3219 / A.3); color value (Hazen): ≤ 40 (M017 - EN 1557); monomeric HDI: ≤ 0.25% (M106 - ISO 10283); equivalent weight: approximately 179; flash point: approximately 203 °C (DIN 53213 / 1); density at 20 °C: approximately 1.15 g / ml (DIN EN ISO 2811), supplied by Covestro. GE - 36 is the triglycidyl ether of propoxylated glycerol (see Scheme 1) (EEW: 620 - 680 grams / equivalent; viscosity: 200 - 320 cp at 25 °C; hydrolyzable chloride: < 0.10%; flash point: > 93 °C, residual epichlorohydrin: < 20 ppm), supplied by CVC Thermoset Specialties (now HUNTSMAN). GA - 240 (see Scheme 2) is the glycidylamine of m - xylylenediamine (CAS No. 63738 - 22 - 7) (epoxy equivalent weight (EEW): 95 - 110 grams / equivalent; specific gravity at 25 °C: 1.14 - 1.16 g / ml; flash point: > 215 °C; color (Gardner): maximum 5; viscosity at 25 °C: 1600 - 3000 cP), supplied by CVC Thermoset Specialties (now HUNSTMAN). NC-514S is a bifunctional glycidyl ether epoxy resin (see Scheme 3) [reddish brown liquid; color number (Gardner): ≤18 (ASTM D1544); viscosity at 25 °C: 1000 - 3000 cP (ASTM D2196); epoxy equivalent weight (EEW): 320 - 420 (ASTM D1652 - 97); hydrolyzable chloride (%): ≤0.5 (ASTM D1726 - 11); volatile matter loss (weight %): ≤0.5 (ASTM D2369 - 98); density at 25 °C: 1.026 Kg / L (ASTM D1475); flash point: >205 °C (ASTM D93)], supplied by Cardolite Corporation. 9000 is trihydroxyphenylethane (CAS No. 87093 - 13 - 8) (see Scheme 4) [average epoxy functionality: 3.0; epoxy equivalent weight (EEW): 160 - 180 g / equivalent; viscosity at 72 °C: 5500 - 6500 cP; color number (Gardner): maximum 2], supplied by CVC Thermoset Specialties (now HUNSTMAN). Bisphenol A diglycidyl ether (CAS No. 1675 - 54 - 3) is supplied by Tokyo Chemical Industry Co., Ltd. N,N - diglycidyl - 4 - glycidyloxyaniline (CAS No. 5026 - 74 - 4) is supplied by Sigma - Aldrich. ATLAS TM ATLAS G - 5000 (non - ionic dispersant) is a polyalkylene glycol ether (color: cream; freezing point: about 30 (DGF method III 46(57); relative density at 25 °C: about 1.0; hydrophilic - lipophilic balance (HLB) value: 16.9; form at 25 °C: waxy solid; acid value: maximum 0.3 mg KOH / g; hydroxyl value: 18 - 22 mg KOH / g), supplied by Croda. TMG-5002L-LQ (nonionic dispersant) is a block copolymer of ethylene oxide and propylene oxide, end-capped with butoxy groups (cloud point: 60.6; form at 25 °C: liquid; acid value: maximum 0.3 mg KOH / g; hydroxyl value: 13 - 16 mg KOH / g; color number (Gardner) maximum 4), supplied by Croda. Methyl ethyl ketone is supplied by Sigma-Aldrich. Polypropylene glycol with a calculated number average molecular weight (Mn) of 2000 Da and an OH value of 56 ± 2 mg KOH / g and polypropylene glycol with a calculated number average molecular weight (Mn) of 1000 Da and an OH value of 112 ± 2 mg KOH / g are supplied by DOW. Any other chemicals not specifically mentioned in this paragraph and used in the Examples section (and unless otherwise specified in the specification) have been supplied by Sigma-Aldrich.

[0501]

[0502]

[0503] 1.2 Preparation of polyurethane A and its aqueous dispersion (the latter abbreviated as 'polyurethane A-AQD')

[0504] Charge a 1-liter flask (equipped with a thermometer and overhead stirrer) with 29.9 grams of dimethylolpropionic acid, 282.1 grams of polypropylene glycol with a calculated number average molecular weight (M n ) of 2000 Da and an OH value of 56 ± 2 mg KOH / g, 166.5 grams of polypropylene glycol with a calculated number average molecular weight (M n ) of 1000 Da and an OH value of 112 ± 2 mg KOH / g, and 262.8 grams of isophorone diisocyanate (the number average molecular weight of each of the polyols was calculated from its OH value according to the following equation: M n= 2 * 56100 / (OH value in mg KOH / g of polypropylene glycol). The reaction mixture was placed under a N2 atmosphere and heated to 50 °C, and subsequently 0.07 g of dibutyltin dilaurate was added to the reaction mixture. An exothermic reaction was observed; however, appropriate measures were needed to keep the reaction temperature from exceeding 97 °C. The reaction was maintained at 95 °C for one hour. As determined according to ISO 14896 Method A (2009), the NCO content of the resulting polyurethane A on a solids basis was 7.00% (theoretically 7.44%), and the acid value of polyurethane A was 16.1 ± 1 mg KOH / g of polyurethane A. Polyurethane A was cooled to 60 °C, and 18.7 g of triethylamine was added, and the resulting mixture was stirred for 30 minutes. Subsequently, an aqueous dispersion of polyurethane A (abbreviated as 'polyurethane A - AQD') was prepared as follows: The mixture of polyurethane A and triethylamine thus prepared was fed into a mixture of 1100 g of demineralized water, 19.5 g of nonylphenol ethoxylate (9 ethoxylate groups), and 4.0 g of triethylamine over a 60 - minute period at room temperature. After the feeding was completed, the mixture was stirred for an additional 5 minutes, and then 111.2 g of hydrazine (16 wt% aqueous solution) was added to the mixture. The aqueous dispersion of polyurethane A thus prepared was stirred for an additional 1 h.

[0505] 1.3 Determination of the molecular weights of the AZ1 compound to the AZ5 compounds and component T (matrix - assisted laser desorption / ionization time - of - flight mass spectrometry; MALDI - TOF MS)

[0506] All MALDI - ToF - MS spectra were obtained using a Bruker UltrafleXtreme TMObtained using a MALDI-ToF mass spectrometer. The instrument is equipped with a Nd:YAG laser emitting at 1064 nm and a collision cell (not used for these samples). Using a reflector, spectra were obtained in positive ion mode using the highest resolution mode that provides accurate mass (range 60 - 7000 m / z). Mass calibration was performed using cesium triiodide (range 0.3 - 3.5 kDa) (calibration method: IAV molecular characterization, code MC-MS-05). The laser energy was 20%. The sample was dissolved in THF at approximately 50 mg / mL. The matrix used was: DCTB (trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]malononitrile), CAS number 300364-84-5. The matrix solution was prepared by dissolving 20 mg in 1 mL of THF. Potassium trifluoroacetate (KTFA, CAS number: 2923-16-2) or alternatively sodium iodide was used as the salt (NaI, CAS number 7681-82-5); 10 mg was dissolved in 1 mL of THF with one drop of MeOH. The sample:matrix:salt ratio = 10:200:10 (μL), and after mixing, 0.5 μL was spotted onto the MALDI plate and air-dried for 20 minutes. The reported signal is the main peak within 0.5 Da of the calculated mass of the polyaziridine compound present in the composition in the largest amount theoretically. In all cases, the reported peaks are sodium or potassium adducts of the measured ions. The reported MALDI-TOF MS signal corresponds to the main peak (sodium and potassium cations) of the measured ions of the sodium or potassium adduct of the theoretical formula of the polyaziridine compound. The theoretical formula of the polyaziridine compound can be determined by analytical techniques well-known to those skilled in the art of analytical chemistry, such analytical techniques being for example NMR spectroscopy and / or liquid chromatography-mass spectrometry (LC-MS), and / or liquid chromatography-mass spectrometry-mass spectrometry (LC-MS-MS), and / or theoretically from its preparation method (if the reactants and conditions are known); once the theoretical formula of the polyaziridine compound is determined, its theoretical molecular weight can be determined.

[0507] Polyaziridine compounds are identified by comparing the molecular weight (MW) defined below exactly with the exact molecular weight of the theoretical structure (i.e., the sum of the non-isotopic average atomic masses of its constituent atoms) using a maximum deviation of 0.5 Da. In the context of this specification, the molecular weight (MW) attributed to a polyaziridine compound is calculated by the following equation:

[0508] MW = Observed [M + M 阳离子 -[M 阳离子

[0509] where

[0510] M 阳离子 ​is the exact molar mass of sodium (22.99 Da) or potassium cation (38.96 Da), depending on which cation is used in the MALDI-TOF MS method, and

[0511] The observed [M+M 阳离子 is the MALDI-TOF MS signal (peak) corresponding to the theoretical formula of the polyaziridine compound.

[0512] 1.4 Determination of the average hydrodynamic diameter based on scattering intensity of particles (‘Dynamic Light Scattering - DLS’)

[0513] The average hydrodynamic diameter (D H ) of the particles based on scattering intensity was determined using the method from ISO 22412:2017 with a Malvern Zetasizer Nano S90 DLS instrument operating under the following settings. As the material, polystyrene latex was defined to have an RI of 1.590 at 25 °C, an absorbance of 0.10 for demineralized water continuous medium with a viscosity of 0.8812 cP and an RI of 1.332. Measurements were performed in a DTS0012 disposable cuvette obtained from Malvern Instruments (Malvern, Worcestershire, United Kingdom). The measurements were performed at a backscattering angle of 173 °C. After a 120 - second equilibration, 3 measurements were averaged and consisted of 10 - 15 sub - runs optimized by the machine itself. The focus of the laser was at a fixed position of 4.65 cm, and the data was analyzed using a general data - fitting procedure. Samples were prepared by diluting 0.05 g of the sample (aqueous dispersion) in approximately 5 mL of demineralized water. If the sample still appeared turbid, it was further diluted with distilled water until the sample became almost transparent.

[0514] 1.5 Assessment of chemical resistance

[0515] The initial and end chemical resistance of the test film (cured coating) was tested based on DIN 68861 - 1:2011 - 01.

[0516] The film was prepared as follows: A certain amount of the aqueous dispersion sample and a certain amount of polyurethane A-AQD were mixed together under continuous stirring; these amounts were calculated based on a molar ratio of the number of moles of aziridine rings present in the organic compound with an aziridine ring (e.g., AZ component) (or a mixture of organic compounds) to the number of moles of carboxylic acid functional groups present in polyurethane A equal to 0.9. After the mixing was completed, the resulting mixture was stirred for an additional 30 minutes, thereby producing an aqueous coating composition. This aqueous coating composition was filtered and then applied to a Leneta test card using a 100 μm wire bar coater. Subsequently, the film was dried at 25 °C for 1 h and then annealed at 50 °C for 16 h.

[0517] Cotton pads (1×1 cm) were soaked in a solution of ethanol:demineralized water (1:1). Then they were placed on the film and covered with a petri dish for 1 h. After that, the pads and the petri dish were removed; after 1 h, the coating was visually inspected for damage; the degree of damage was evaluated according to the following rating scheme:

[0518] 5: No visible change

[0519] 4: Almost no obvious change in gloss or color

[0520] 3: Slight change in gloss or color; the structure of the test surface has not changed

[0521] 2: Obvious significant change; however, the structure of the test surface remains more or less undamaged.

[0522] 1: Obvious significant change; the structure of the test surface has changed.

[0523] 0: The surface being tested is severely altered or damaged.

[0524] In the context of this specification, the above integers 0 - 5 are referred to as 'rating points'.

[0525] The chemical resistance of the reference film (prepared only from polyurethane A-AQD) is poor (this applies to all examples and comparative examples of the present invention shown in the examples).

[0526] 1.6 Evaluation of storage stability and crosslinking efficiency

[0527] The storage stability of the organic compound with an aziridine ring in the aqueous composition [or equivalently, the storage stability of the aqueous dispersion comprising the organic compound with an aziridine ring] is evaluated by viscosity measurement (initial and final viscosities) and determination of chemical resistance (initial and final chemical resistances), both of which are explained in this specification.

[0528] The crosslinking efficiency of an organic compound having an aziridine ring in an aqueous composition [or equivalently, the crosslinking efficiency of an aqueous dispersion comprising an organic compound having an aziridine ring] is evaluated by determining the final chemical resistance of the film (cured coating).

[0529] Step 1:

[0530] Prepare an aqueous dispersion comprising an organic compound having an aziridine ring and determine its initial viscosity as described in this specification.

[0531] In addition, the initial chemical resistance of the aqueous dispersion was also determined as described in this specification.

[0532] Step 2:

[0533] Thereafter, the aqueous dispersion is stored in an oven at 50 °C for 4 weeks. At the end of this time period, the aqueous dispersion is removed from the oven and allowed to cool to room temperature.

[0534] Subsequently:

[0535] i) Determine the final viscosity of the aqueous dispersion as described in this specification, and

[0536] ii) Determine the final chemical resistance of the aqueous dispersion as described in this specification.

[0537] For obvious reasons, an entity that gels during storage at an elevated temperature for an extended period is considered to not have enhanced storage stability because it is considered to not have a processable viscosity.

[0538] For obvious reasons, an entity that gels during storage at an elevated temperature for an extended period is considered to have poor crosslinking efficiency.

[0539] 1.7 Determination of Apparent Viscosity

[0540] Measure the initial and final apparent viscosities (or equivalently, the initial and final viscosities) at room temperature at 60 rpm on a Brookfield DVE-LV viscometer (single cylinder geometry). Select a spindle from spindles S62, S63, or S64, using the smallest numbered spindle (i.e., the largest spindle) that gives a torque reading between 10% and 100%.

[0541] 1.8 Determination of pH

[0542] Determine the pH of the sample according to ISO 976:2013. Measure the sample at room temperature using a Metrohm 691 pH meter equipped with a combined glass electrode and a PT-1000 temperature sensor. Calibrate the pH meter using buffer solutions of pH 7.00 and 9.21 before use.

[0543] 1.9 Determination of Acid Value

[0544] The acid value of the polymer was determined according to ASTM D1639-90(1996)e1. According to the procedure, a sample dissolved in a good solvent was titrated with an alcoholic potassium hydroxide (KOH) solution of known concentration. According to the following formula, the difference in titration volume between the sample and the blank is a measure of the solid acid value:

[0545] AV = [(V 空白 - V 样本 ) * N KOH * 56.1] / (W * S / 100)

[0546] where

[0547] AV is the solid acid value in mg KOH / g of solid material, V 空白 is the volume of the KOH solution used in the blank, V 样本 is the volume of the KOH solution used in the sample, N KOH is the normality of the KOH solution, W is the sample weight in grams, and S is the solid content of the sample in %. The measurement was carried out in duplicate using a potentiometric end point on a Metrohm 702SM Titrino titrator (the measurement results are accepted if the difference between duplicate runs is < 0.1 mg KOH / g of solid material).

[0548] 1.10 Determination of NCO Content

[0549] The NCO content of the sample was determined according to ASTM D2572-19. In this procedure, the sample was reacted with an excess of dibutylamine. Subsequently, the excess dibutylamine was back-titrated with standard 1N hydrochloric acid (HCl). According to the following formula, the difference in titration volume between the sample and the blank is a measure of the isocyanate content in terms of solids:

[0550] % NCO 固体 = [(V b - V m ) * N * 4.2] / (A * s / 100)

[0551] where

[0552] % NCO 固体 is the isocyanate content in terms of solids, V b is the volume of HCl used in the blank, V mV is the volume of HCl used in the sample, N is the normality of the HCl solution, A is the weight of the sample in grams, and s is the solids content of the sample in %. The measurements are performed in duplicate using a potentiometric end point on a Metrohm 702SM Titrino titrator (the measurement results are accepted if the difference between duplicate runs < 0.1% NCO , then the measurement results are accepted).

[0553] 1.11 Determination of the amount of component T [Liquid chromatography - mass spectrometry (LC - MS)]

[0554] The amount of component T (as defined herein; weight % of the total weight of the AZ compound) is determined by liquid chromatography coupled with mass spectrometry (LC - MS). Initially, a 0.01 wt% solution of the sample in methanol is prepared. Subsequently, 0.5 μL of this solution is injected into an Agilent 1290 Infinity II ultra - high - pressure liquid chromatography (UHPLC) system equipped with: a) a C18 type T3 column of high - strength silica (HSS) technology supplied by operating at 40 °C [100×2.1 mm (length × diameter); stationary phase with an average particle size of 1.8 microns], and b) an Agilent 6550 iFunnel QTOF detector [electrospray ionization - time - of - flight mass spectrometer (ESI - TOF - MS) detector]. Once the sample is injected, a gradient of the mobile phase is then used at a flow rate of 0.5 mL / min [from 80 / 20 v / v A / B to 1 / 99 v / v A / B, where A is 10 mM CH3COO - NH4 + (set to pH 9.0 with NH3) and B is acetonitrile; A and B constitute the mobile phase] for 10 min to separate the various components of the sample. Subsequently, a gradient of the mobile phase is applied at a flow rate of 0.5 mL / min [from 1 / 99 v / v A / B to 1 / 49 / 50 A / B / C, where A is 10 mM CH3COO - NH4 + (set to pH 9.0 with NH3), B is acetonitrile, and C is tetrahydrofuran (THF); A, B, and C constitute the mobile phase] for 5 min to clean the column. Assuming that all components of the sample have a linear MS response over all response ranges and all components of the sample have equal ionization efficiency, the signals of the following substances are integrated:

[0555] - Total ion current, and

[0556] - Extracted ion chromatogram of component T.

[0557] Data acquisition was performed using MassHunter Build 10.1.48 software supplied by Agilent, while data processing was carried out using Qualitative Analysis Build 10.0.10305.0 software, also supplied by Agilent.

[0558] The amount of component T (weight % of the total weight of the AZ compound) was determined by dividing the integral of the extracted ion chromatogram of component T by the integral of the total ion current and multiplying by 100.

[0559] 1.12 Determination of the amount of chloride

[0560] The amount of chloride in the aqueous dispersion was determined according to ASTM D1726-11(2019).

[0561] 2. Examples of the present invention

[0562] Example 1

[0563] 100 grams of GE-36, 26.5 grams of propyleneimine and 5 grams of potassium carbonate were charged into a reaction flask equipped with a thermometer and a condenser connected to a cryostat (3 °C). The mixture was stirred with a mechanical overhead stirrer under a nitrogen atmosphere. Then the mixture was heated to 80 °C. Samples were taken at regular intervals and the reaction progress was monitored using 1 1H-NMR until no signal (chemical shift) related to the epoxy protons from the polyfunctional epoxide was observed. The reaction mixture was diluted with toluene and filtered. The solvent and the excess propyleneimine were removed from the filtrate under vacuum to obtain a clear, highly viscous liquid. The theoretical formula of the thus-prepared (aziridinylhydroxy)-functional organic compound is shown below (where x + y + z = 33), and the theoretical molecular weight was calculated to be 2346.68 Da.

[0564]

[0565] The molecular weight defined and determined by MALDI-TOF MS - as thus defined and described in this specification - is 2346.50 Da (the observed [M + M Na+ -[M Na+ ).

[0566] Subsequently, 15 grams of the above-obtained (aziridinylhydroxy)-functional organic compound was mixed with 3.2 grams of methyl ethyl ketone and incubated at 50 °C until a homogeneous solution was obtained. 0.03 grams of triethylamine (TEA) and 3 grams of molten ATLAS TMG-5000 (dispersant) was added to the solution. An IKA T25 Digital Ultra- mixer with an S25N-18G head was used to stir the resulting mixture at 2000 rpm for 5 minutes at room temperature. Then, the stirring speed was increased to 10,000 rpm, and 15 grams of demineralized water and triethylamine were gradually added to the mixture within 15 minutes to adjust the pH to 11. During this addition process, the mixer was continuously moved around the reaction vessel. After the addition was completed, the resulting dispersion was stirred at 5000 rpm for another 10 minutes, and the pH of the dispersion was adjusted to 11 again with triethylamine. The aqueous dispersion thus prepared contains the particles of the present invention (which are dispersed in water).

[0567] The particles of the present invention have an average hydrodynamic diameter (D H ) based on the scattering intensity of 275 nm.

[0568] Evaluation of storage stability and crosslinking efficiency

[0569] Initial viscosity (spindle S62): 260 mPa·s

[0570] Final viscosity (spindle S62): 320 mPa·s

[0571] The final viscosity is 1.23 times the initial viscosity (final viscosity / initial viscosity = 1.23).

[0572] Therefore, the aqueous dispersion has a viscosity that is easy to process.

[0573] The initial chemical resistance is very good.

[0574] The final chemical resistance is very good.

[0575] The final chemical resistance is equal to the initial chemical resistance.

[0576] The crosslinking efficiency is very good.

[0577] In view of the above results, the particles of the present invention and / or the aqueous dispersion of the present invention containing the particles of the present invention have surprisingly enhanced storage stability at elevated temperatures for an extended period of time (4 weeks at 50 °C) because:

[0578] i) They have a viscosity that is easy to process, and

[0579] ii) The final chemical resistance is equal to the initial chemical resistance,

[0580] while maintaining a very good crosslinking efficiency because the final chemical resistance is very good.

[0581] Example 2

[0582] 30.0 g of NC-514S, 19.2 g of propyleneimine, 30 g of toluene, and 3 g of potassium carbonate were charged into a reaction flask equipped with a thermometer and a condenser connected to a cryostat (3 °C). The mixture was stirred with a mechanical stirrer under a nitrogen atmosphere. Then, the mixture was heated to 70 °C. Samples were taken at regular intervals and the progress of the reaction was monitored using 1 1H-NMR until no signal (chemical shift) related to the epoxy protons from the polyfunctional epoxide was observed. After 20 h of reaction, the mixture was diluted with toluene and filtered. The solvent and excess propyleneimine were removed in vacuo from the filtrate to obtain a high-viscosity brown oil. The theoretical formula of the thus-prepared (aziridinylhydroxy)-functional organic compound is shown below, and the theoretical molecular weight was calculated to be 622.47 Da.

[0583]

[0584] The molecular weight defined and determined by MALDI-TOF MS—as so defined and described in this specification—is 622.43 Da (the observed [M + M Na+ − [M Na+ ).

[0585] Subsequently, 18.4 g of the above-obtained (aziridinylhydroxy)-functional organic compound was mixed with 9.2 g of methyl ethyl ketone and incubated at 50 °C until a homogeneous solution was obtained. 0.03 g of triethylamine (TEA) and 3.7 g of molten ATLAS TM G-5000 (dispersant) were added to the solution. The resulting mixture was stirred at 2000 rpm for 5 min at room temperature using an IKA T25 Digital Ultra- Turrax mixer with an S25N-18G head. Then, the stirring speed was increased to 10,000 rpm, and 27.5 g of demineralized water and triethylamine were gradually added to the mixture over 15 min to adjust the pH to 11. During this addition process, the Turrax mixer was continuously moved around the reaction vessel. After the addition was complete, the resulting dispersion was stirred at 5000 rpm for an additional 10 min, and the pH of the dispersion was adjusted to 11 again with triethylamine. The aqueous dispersion thus prepared contains the particles of the present invention (which are dispersed in water).

[0586] The particles of the present invention have an average hydrodynamic diameter (D H ) based on the scattering intensity of 181 nm.

[0587] Evaluation of storage stability and crosslinking efficiency

[0588] Initial viscosity (spindle S62): 132 mPa·s

[0589] Final viscosity (spindle S62): 138 mPa·s

[0590] The final viscosity is 1.05 times the initial viscosity (final viscosity / initial viscosity = 1.05).

[0591] Therefore, the aqueous dispersion has a viscosity that is easy to process.

[0592] The initial chemical resistance is good.

[0593] The final chemical resistance is good.

[0594] The final chemical resistance is equal to the initial chemical resistance.

[0595] The crosslinking efficiency is good.

[0596] In view of the above results, the particles of the present invention and / or the aqueous dispersion of the present invention containing the particles of the present invention have surprisingly enhanced storage stability at elevated temperatures for an extended period of time (4 weeks at 50 °C) because:

[0597] i) They have a viscosity that is easy to process, and

[0598] ii) The final chemical resistance is equal to the initial chemical resistance,

[0599] while maintaining good crosslinking efficiency because the final chemical resistance is good.

[0600] Example 3

[0601] 30.0 g of NC-514S, 19.2 g of propyleneimine, 30 g of toluene, and 3 g of potassium carbonate were charged into a reaction flask equipped with a thermometer and a condenser connected to a cryostat (3 °C). The mixture was stirred with a mechanical stirrer under a nitrogen atmosphere. Then the mixture was heated to 70 °C. Samples were taken at regular intervals and the reaction progress was monitored using 1 1H-NMR until no signal (chemical shift) related to the epoxy protons from the polyfunctional epoxide was observed. After 20 hours of reaction, the mixture was diluted with toluene and filtered. The solvent and excess propyleneimine were removed in vacuo from the filtrate to obtain a high-viscosity brown oil. The theoretical formula of the (aziridinylhydroxy)-functional organic compound thus prepared is shown below, and the theoretical molecular weight was calculated to be 622.47 Da.

[0602]

[0603] The molecular weight defined and determined by MALDI-TOF MS - as so defined and described in this specification - is 622.43 Da (the observed [M + M Na+ -[M Na+ ).

[0604] Subsequently, 18.7 g of the above-obtained (aziridinylhydroxy)-functional organic compound was mixed with 9.6 g of acetone and incubated at 50 °C until a homogeneous solution was obtained. 0.03 g of triethylamine (TEA) and 3.8 g of molten Atlas TM G-5002L-LQ (dispersant) were added to the solution. The resulting mixture was stirred at 2000 rpm for 5 minutes at room temperature using an IKA T25 Digital Ultra- mixer with an S25N-18G head. Then, the stirring speed was increased to 10,000 rpm, and 24.0 g of demineralized water and triethylamine were gradually added to the mixture over 15 minutes to adjust the pH to 11. During this addition process, the mixer was continuously moved around the reaction vessel. After the addition was complete, the resulting dispersion was stirred at 5000 rpm for an additional 10 minutes, and the pH of the dispersion was again adjusted to 11 with triethylamine. The aqueous dispersion thus prepared contains the particles of the present invention (which are dispersed in water).

[0605] The particles of the present invention have an average hydrodynamic diameter (D H ) based on the scattering intensity of 153 nm.

[0606] Evaluation of storage stability and crosslinking efficiency

[0607] Initial viscosity (spindle S62): 1178 mPa·s

[0608] Final viscosity (spindle S62): 1212 mPa·s

[0609] The final viscosity is 1.03 times the initial viscosity (final viscosity / initial viscosity = 1.03).

[0610] Therefore, the aqueous dispersion has a viscosity that is easy to process.

[0611] The initial chemical resistance is good.

[0612] The final chemical resistance is good.

[0613] The final chemical resistance is equal to the initial chemical resistance.

[0614] The crosslinking efficiency is good.

[0615] In view of the above results, the particles of the present invention and / or the aqueous dispersions of the present invention comprising the particles of the present invention have surprisingly enhanced storage stability at elevated temperatures for an extended period of time (4 weeks at 50 °C) because:

[0616] i) They have a viscosity that is easy to process, and

[0617] ii) the end chemical resistance is equal to the starting chemical resistance,

[0618] while maintaining good crosslinking efficiency because the end chemical resistance is good.

[0619] Example 4

[0620] 30.0 grams of NC-514S, 19.2 grams of propyleneimine, 30 grams of toluene and 3 grams of potassium carbonate were charged into a reaction flask equipped with a thermometer and a condenser connected to a cryostat (3 °C). The mixture was stirred with a mechanical stirrer under a nitrogen atmosphere. Then the mixture was heated to 70 °C. Samples were taken at regular intervals and the progress of the reaction was monitored using 1 1H-NMR until no signal (chemical shift) related to the epoxy protons from the polyfunctional epoxide was observed. After 20 hours of reaction, the mixture was diluted with toluene and filtered. The solvent and excess propyleneimine were removed in vacuo from the filtrate to obtain a high-viscosity brown oil. The theoretical formula of the thus-prepared (aziridinylhydroxy)-functional organic compound is shown below, and the theoretical molecular weight was calculated to be 622.47 Da.

[0621]

[0622] The molecular weight defined and determined by MALDI-TOF MS - as thus defined and described in this specification - is 622.43 Da (the observed [M+M Na+ -[M Na+ ).

[0623] Subsequently, 25.4 grams of the above-obtained (aziridinylhydroxy)-functional organic compound was mixed with 12.7 grams of methyl ethyl ketone and incubated at 50 °C until a homogeneous solution was obtained. 0.03 grams of triethylamine (TEA) and 5.1 grams of molten ATLAS TM G-5000 (dispersant) were added to the solution. Using an IKA T25 Digital Ultra- with an S25N-18G head The mixer stirred the resulting mixture at 2000 rpm for 5 minutes at room temperature. Then, the stirring speed was increased to 10000 rpm, and 38.0 grams of demineralized water and triethylamine were gradually added to the mixture within 15 minutes to adjust the pH to 11. During this addition process, the mixer continuously moved around the reaction vessel. After the addition was completed, the resulting dispersion was stirred at 5000 rpm for another 10 minutes, and the pH of the dispersion was adjusted to 12.5 with potassium hydroxide. The aqueous dispersion thus prepared contains the particles of the present invention (which are dispersed in water).

[0624] The particles of the present invention have an average hydrodynamic diameter (D H ) based on scattering intensity of 176 nm.

[0625] Evaluation of storage stability and crosslinking efficiency

[0626] Initial viscosity (spindle S62): 182 mPa·s

[0627] Final viscosity (spindle S62): 220 mPa·s

[0628] The final viscosity is 1.21 times the initial viscosity (final viscosity / initial viscosity = 1.21).

[0629] Therefore, the aqueous dispersion has a viscosity that is easy to process.

[0630] The initial chemical resistance is good.

[0631] The final chemical resistance is good.

[0632] The final chemical resistance is equal to the initial chemical resistance.

[0633] The crosslinking efficiency is good.

[0634] In view of the above results, the particles of the present invention and / or the aqueous dispersion of the present invention containing the particles of the present invention have surprisingly enhanced storage stability at elevated temperatures for an extended period of time (4 weeks at 50 °C) because:

[0635] i) They have a viscosity that is easy to process, and

[0636] ii) the final chemical resistance is equal to the initial chemical resistance,

[0637] while maintaining good crosslinking efficiency because the final chemical resistance is good.

[0638] Example 5

[0639] 30.0 grams of NC-514S, 19.2 g of propyleneimine, 30 g of toluene, and 3 g of potassium carbonate were charged into a reaction flask equipped with a thermometer and a condenser connected to a cryostat (3 °C). The mixture was stirred with a mechanical stirrer under a nitrogen atmosphere. Then the mixture was heated to 70 °C. Samples were taken at regular intervals and the progress of the reaction was monitored using 1 1H-NMR until no signal (chemical shift) related to the epoxy protons from the polyfunctional epoxide was observed. After 20 h of reaction, the mixture was diluted with toluene and filtered. The solvent and excess propyleneimine were removed in vacuo from the filtrate to obtain a high-viscosity brown oil. The theoretical formula of the (aziridinylhydroxy)-functional organic compound thus prepared is shown below, and the theoretical molecular weight was calculated to be 622.47 Da.

[0640]

[0641] The molecular weight defined and determined by MALDI-TOF MS — as so defined and described in this specification — is 622.43 Da (the observed [M + M Na+ - [M Na+ ).

[0642] In a separate reaction, 75 g of 9000 was dissolved in 75 mL of toluene and charged into a reaction flask equipped with a thermometer and a condenser connected to a cryostat (3 °C). Next, 55 g of propyleneimine and 5 g of potassium carbonate were added to the flask. The mixture was stirred with a mechanical overhead stirrer under a nitrogen atmosphere. Then the mixture was heated to 80 °C. Samples were taken at regular intervals and the progress of the reaction was monitored using 1 1H-NMR until no signal (chemical shift) related to the epoxy protons from the polyfunctional epoxide was observed. After 22 h of reaction, the mixture was filtered. The solvent and excess propyleneimine were removed in vacuo from the filtrate to obtain an off-white solid. The theoretical formula of the (aziridinylhydroxy)-functional organic compound thus prepared is shown below, and the theoretical molecular weight was calculated to be 645.38 Da.

[0643]

[0644] The molecular weight defined and determined by MALDI-TOF MS — as so defined and described in this specification — is 645.37 Da (the observed [M + M Na+ - [M Na+ ).

[0645] Subsequently, 2.3 g or more of the (aziridinylhydroxy) functional organic compound with a theoretical molecular weight of 645.38 Da and 6.4 g or more of the (aziridinylhydroxy) functional organic compound with a theoretical molecular weight of 622.47 Da were mixed with 2.4 g of toluene and 2.0 g of methyl ethyl ketone, and incubated at 50 °C until a homogeneous solution was obtained. 0.03 g of triethylamine (TEA) and 1.8 g of molten ATLAS TM G-5000 (dispersant) were added to the solution. Using an IKA T25 Digital Ultra- mixer with an S25N-18G head, the resulting mixture was stirred at 2000 rpm for 5 minutes at room temperature. Then, the stirring speed was increased to 10000 rpm, and 45.5 g of demineralized water and triethylamine were gradually added to the mixture over 15 minutes to adjust the pH to 11. During this addition process, the mixer was continuously moved around the reaction vessel. After the addition was complete, the resulting dispersion was stirred at 5000 rpm for another 10 minutes, and the pH of the dispersion was further adjusted to 11 with triethylamine. The aqueous dispersion thus prepared contains the particles of the present invention (which are dispersed in water).

[0646] The particles of the present invention have an average hydrodynamic diameter (D H ) based on scattering intensity of 397 nm.

[0647] Evaluation of storage stability and crosslinking efficiency

[0648] Initial viscosity (spindle S62): 14 mPa·s

[0649] Final viscosity (spindle S62): 41 mPa·s

[0650] The final viscosity is 2.93 times the initial viscosity (final viscosity / initial viscosity = 2.93).

[0651] Therefore, the aqueous dispersion has a viscosity that is easy to process.

[0652] The initial chemical resistance is good.

[0653] The final chemical resistance is good.

[0654] The final chemical resistance is equal to the initial chemical resistance.

[0655] The crosslinking efficiency is good.

[0656] In view of the above results, the particles of the present invention and / or the aqueous dispersion of the present invention containing the particles of the present invention have surprisingly enhanced storage stability at elevated temperatures for an extended period of time (4 weeks at 50 °C) because:

[0657] i) They have a viscosity that is easy to process, and

[0658] ii) the end chemical resistance is equal to the starting chemical resistance,

[0659] while maintaining good crosslinking efficiency, because the end chemical resistance is good.

[0660] Example 6

[0661] Dissolve 180 g of N 3900 in 150 g of toluene, charge into a reaction flask equipped with a thermometer and heat to 50 °C. Next, add 0.05 g of triethylamine to the flask and slowly add 74 g of glycidyl to the reaction mixture over a 150-minute period while ensuring that the reaction temperature remains constant between 55 - 58 °C. After stirring for an additional 60 minutes at this temperature, cool the mixture to room temperature and stir at room temperature for 18 hours. Remove the solvent under vacuum and transfer the resulting pale yellow oil to a reaction flask equipped with a thermometer and a condenser connected to a cryostat (3 °C). Next, add 250 g of toluene, 175 g of propyleneimine, and 10 g of potassium carbonate to the flask. Stir the mixture with a mechanical overhead stirrer under a nitrogen atmosphere. Then heat the mixture to 60 °C. Sample at regular intervals and monitor the reaction progress using 1 1H-NMR until no signal (chemical shift) related to the epoxy protons from the polyfunctional epoxide is observed. After 18 hours of reaction, filter the mixture. Remove the solvent and excess propyleneimine from the filtrate under vacuum to obtain a high-viscosity liquid. The theoretical formula of the thus-prepared (aziridinylhydroxy)-functional organic compound is shown below, and the theoretical molecular weight is calculated to be 897.55 Da.

[0662]

[0663] The molecular weight defined and determined by MALDI-TOF MS - as thus defined and described in this specification - is 897.56 Da (the observed [M + M Na+ -[M Na+ ).

[0664] Subsequently, dissolve 4.2 g of B-300 in 4.2 g of methyl ethyl ketone. In parallel, mix 4.2 g of the above-obtained (aziridinylhydroxy)-functional organic compound with 2.1 g of methyl ethyl ketone. Mix the two solutions and incubate at 50 °C until a homogeneous mixture is obtained. Add 0.03 g of triethylamine (TEA) and 2.5 g of molten ATLAS TMG-5000 (dispersant) was added to the solution. An IKA T25 Digital Ultra- mixer with an S25N-18G head was used to stir the resulting mixture at 2000 rpm for 5 minutes at room temperature. Then, the stirring speed was increased to 10,000 rpm, and 15.4 grams of demineralized water and triethylamine were gradually added to the mixture over 15 minutes to adjust the pH to 11. During this addition process, the mixer was continuously moved around the reaction vessel. After the addition was completed, the resulting dispersion was stirred at 5000 rpm for another 10 minutes. Then, the solvent was removed using a rotary evaporator, an equal amount of demineralized water was added, and the pH of the dispersion was adjusted to 11 again with triethylamine. The aqueous dispersion thus prepared contains the particles of the present invention (which are dispersed in water).

[0665] The particles of the present invention have an average hydrodynamic diameter (D H ) based on the scattering intensity of 100 nm.

[0666] Evaluation of storage stability and crosslinking efficiency

[0667] Initial viscosity (spindle S62): 39 mPa·s

[0668] Final viscosity (spindle S62): 40 mPa·s

[0669] The final viscosity is 1.03 times the initial viscosity (final viscosity / initial viscosity = 1.03).

[0670] Therefore, the aqueous dispersion has a viscosity that is easy to process.

[0671] The initial chemical resistance is good.

[0672] The final chemical resistance is good.

[0673] The final chemical resistance is equal to the initial chemical resistance.

[0674] The crosslinking efficiency is good.

[0675] In view of the above results, the particles of the present invention and / or the aqueous dispersion of the present invention containing the particles of the present invention have surprisingly enhanced storage stability at elevated temperatures for an extended period of time (4 weeks at 50 °C) because:

[0676] i) They have a viscosity that is easy to process, and

[0677] ii) The final chemical resistance is equal to the initial chemical resistance,

[0678] while maintaining good crosslinking efficiency because the final chemical resistance is good.

[0679] 3. Comparative Example

[0680] Example 1C

[0681] Trimethylolpropane tris(2-methyl-1-aziridinepropionate) (trade name ‘Crosslinking Agent CX-100’) has the following structure:

[0682]

[0683] And the theoretical molecular weight is calculated to be 467.30 Da.

[0684] 7.5 g of trimethylolpropane tris(2-methyl-1-aziridinepropionate) was mixed with 3.75 g of acetone and incubated at 50 °C until a homogeneous solution was obtained. Subsequently, 0.03 g of triethylamine and 0.75 g of molten Atlas TM G-5000 dispersant were added to the solution. The resulting mixture was stirred at 2000 rpm for 5 minutes at room temperature using an IKA T25 Digital Ultra- mixer with an S25N-18G head. Then, the stirring speed was increased to 10,000 rpm, and 7.5 g of demineralized water and an amount of triethylamine for adjusting the pH to 10 were gradually added to the mixture over 15 minutes. During this addition process, the mixer was continuously moved around the reaction vessel. After the addition was complete, the mixture was stirred at 5000 rpm for an additional 10 minutes, and the pH of the mixture was set to 10 using triethylamine. This produced a homogeneous solution free of any particles.

[0685] Evaluation of storage stability and crosslinking efficiency

[0686] Initial viscosity (spindle S62): 178 mPa·s

[0687] Final viscosity (spindle S62): Unable to measure because the aqueous composition gelled during the 2nd week of storage

[0688] Therefore, the aqueous composition does not have a processable viscosity.

[0689] The initial chemical resistance is excellent.

[0690] The final chemical resistance is unable to measure because the aqueous composition gelled during the 2nd week of storage.

[0691] Therefore, the crosslinking efficiency is poor.

[0692] In view of the above results, trimethylolpropane tris(2-methyl-1-aziridinepropionate) and / or its solution failed to provide enhanced storage stability at elevated temperatures for an extended period (4 weeks at 50 °C) because they did not have a processable viscosity and, at the same time, failed to maintain good crosslinking efficiency.

[0693] Example 2C

[0694] 299 g of bisphenol A diglycidyl ether, 250 g of toluene, 255 g of propyleneimine, and 10 g of potassium carbonate were charged into a reaction flask equipped with a thermometer and a condenser connected to a cryostat (3 °C). The mixture was stirred with a mechanical overhead stirrer under a nitrogen atmosphere. The mixture was then heated to 70 °C. Samples were taken at regular intervals and the progress of the reaction was monitored using 1 1H-NMR until no signals (chemical shifts) related to the epoxy protons from the polyfunctional epoxide were observed. After 19 hours of reaction, the mixture was filtered. The solvent and excess propyleneimine were removed from the filtrate under vacuum to obtain a highly viscous liquid. The theoretical formula of the polyaziridine compound thus prepared is shown below, and the theoretical molecular weight was calculated to be 454.28 Da.

[0695]

[0696] The molecular weight defined and determined by MALDI-TOF MS - as thus defined and described in this specification - is 454.26 Da (the observed [M + M Na+ - [M Na+ ).

[0697] 6.95 g of the above-obtained polyaziridine compound was mixed with 5.00 g of methyl ethyl ketone (MEK) and incubated at 50 °C until a homogeneous solution was obtained. Subsequently, 0.03 g of triethylamine and 1.20 g of molten Atlas TM G-5000 dispersant were added to the solution. The resulting mixture was stirred at 2000 rpm for 5 minutes at room temperature using an IKA T25 Digital Ultra- Turrax with an S25N-18G head. Then, the stirring was increased to 10000 rpm and 7.5 g of demineralized water was gradually added to the mixture over 15 minutes. During this addition process, the Turrax was continuously moved around the reaction vessel. After the addition was complete, the resulting mixture was stirred at 5000 rpm for an additional 10 minutes. The aqueous dispersion thus prepared contained particles (which were dispersed in water).

[0698] The particles had an average hydrodynamic diameter (D H ) based on the scattering intensity of 517 nm.

[0699] Evaluation of storage stability and crosslinking efficiency

[0700] Initial viscosity (spindle S62): 10 mPa.s

[0701] Final viscosity (spindle S62): Unmeasurable because the aqueous composition gelled during the first week of storage

[0702] Therefore, the aqueous composition does not have a processable viscosity.

[0703] The initial chemical resistance is good.

[0704] Final chemical resistance is unmeasurable because the aqueous composition gelled during the first week of storage.

[0705] Therefore, the crosslinking efficiency is poor.

[0706] In view of the above results, the polyaziridine compound and / or its aqueous dispersion obtained above failed to provide enhanced storage stability at elevated temperatures for an extended period (4 weeks at 50 °C) because they do not have a processable viscosity and, at the same time, failed to maintain good crosslinking efficiency.

[0707] Example 3C

[0708] 24.0 g of N,N-diglycidyl-4-glycidyloxyaniline, 42.0 g of propyleneimine, 30 g of toluene, and 3 g of potassium carbonate were charged into a reaction flask equipped with a thermometer and a condenser connected to a cryostat (3 °C). The mixture was stirred with a mechanical stirrer under a nitrogen atmosphere. The mixture was then heated to 70 °C. Samples were taken at regular intervals and the reaction progress was monitored using 1 1H-NMR until no signal (chemical shift) related to the epoxy protons from the polyfunctional epoxide was observed. After 24 hours of reaction, the mixture was diluted with toluene and filtered. The solvent and excess propyleneimine were removed in vacuo from the filtrate to obtain a highly viscous yellow material. The theoretical formula of the polyaziridine compound thus prepared is shown below, and the theoretical molecular weight was calculated to be 448.30 Da.

[0709]

[0710] The molecular weight defined and determined by MALDI-TOF MS - as so defined and described in this specification - is 448.29 Da (the observed [M + M Na+ - [M Na+ ).

[0711] This compound is disclosed in col.2, ll.29 - 39 of US 3329674.

[0712] 9.80 g or more of the obtained polyaziridine compound was mixed with 4.90 g of acetone and incubated at 50 °C until a homogeneous solution was obtained. Subsequently, 0.03 g of triethylamine and 1.03 g of molten Atlas TM G - 5000 dispersant was added to the solution. The resulting mixture was stirred at 2000 rpm for 5 minutes at room temperature using an IKA T25 Digital Ultra - mixer with an S25N - 18G head. Then, the stirring was increased to 10000 rpm, and 9.90 g of demineralized water was gradually added to the mixture over 15 minutes. During this addition process, the mixer was continuously moved around the reaction vessel. After the addition was complete, the mixture was stirred at 5000 rpm for an additional 10 minutes, and the pH of the mixture was set to 10 using triethylamine. This produced a homogeneous solution free of any particles.

[0713] Evaluation of storage stability and crosslinking efficiency

[0714] Initial viscosity (spindle S62): 52 mPa.s

[0715] Final viscosity (spindle S62): Unable to measure because the solution gelled during the first week of storage

[0716] Therefore, the solution does not have a processable viscosity.

[0717] The initial chemical resistance is very good.

[0718] The final chemical resistance is unable to measure because the solution gelled during the first week of storage.

[0719] Therefore, the cross - linking efficiency is poor.

[0720] In view of the above results, the polyaziridine compound and / or its solution obtained above failed to provide enhanced storage stability at elevated temperatures for an extended period (4 weeks at 50 °C) because they do not have a processable viscosity and, at the same time, failed to maintain good cross - linking efficiency.

[0721] Example 4C

[0722] 75 g of GA - 240, 80 g of propyleneimine, and 5 g of potassium carbonate were charged into a reaction flask equipped with a thermometer and a condenser connected to a cryostat (3 °C). The mixture was stirred with a mechanical overhead stirrer under a nitrogen atmosphere. Then the mixture was heated to 71 °C. Samples were taken at regular intervals and using 1The reaction progress was monitored by 1H-NMR until no signals (chemical shifts) related to the epoxy protons from the polyfunctional epoxide were observable. After 22 hours of reaction, the mixture was diluted with toluene and filtered. The solvent and excess propyleneimine were removed in vacuo from the filtrate to afford a clear, transparent solid. The theoretical formula of the AZ component is shown below and the theoretical molecular weight was calculated to be 588.44 Da.

[0723]

[0724] The molecular weight defined and determined by MALDI-TOF MS — as thus defined and described in this specification — is 588.48 Da (the observed [M+M Na+ -[M Na+ )).

[0725] 9.68 g of the above transparent solid was mixed with 4.90 g of acetone and incubated at 50 °C until a homogeneous solution was obtained. Subsequently, 0.03 g of triethylamine and 0.96 g of molten Atlas TM G-5000 dispersant were added to the solution. The resulting mixture was stirred for 5 minutes at 2000 rpm at room temperature using an IKA T25 Digital Ultra- turrax with an S25N-18G head. Then, the stirring was increased to 10000 rpm and 9.65 g of demineralized water was gradually added to the mixture over 15 minutes. During this addition, the turrax was continuously moved around the reaction vessel. After the addition was complete, the mixture was stirred for an additional 10 minutes at 5000 rpm and the pH of the mixture was set to 10 using triethylamine. This yielded a homogeneous solution free of any particles.

[0726] Evaluation of storage stability and crosslinking efficiency

[0727] Initial viscosity (spindle S62): 64 mPa·s

[0728] Final viscosity (spindle S62): Not measurable because the solution gelled during the 1st week of storage

[0729] Thus, the solution does not have a processable viscosity.

[0730] The initial chemical resistance is very good.

[0731] The final chemical resistance is not measurable because the solution gelled during the 1st week of storage.

[0732] Thus, the crosslinking efficiency is poor.

[0733] In view of the above results, the polyaziridine compounds and / or their solutions obtained above failed to provide enhanced storage stability at elevated temperatures for an extended period (4 weeks at 50 °C) because they did not have a processable viscosity and, at the same time, failed to maintain good crosslinking efficiency.

[0734] 4. Conclusions

[0735] As detailed in this specification, US 3329674 of Thiokol Chemical Corporation (prior art) neither discloses any particles—let alone any particles of compounds with aziridine groups, let alone these compounds having a molecular weight of at least 600 Da and at most 10,000 Da—nor does it disclose any aqueous dispersion containing particles, said particles comprising an (aziridinylhydroxy)-functional organic component. US 3329674 fails to provide a combination of enhanced storage stability (at elevated temperatures for an extended period; 4 weeks at 50 °C) of an aqueous dispersion containing an organic compound with an aziridine ring and maintaining at least good crosslinking efficiency (the crosslinking efficiency is poor). Evidence in this regard is Example 3C shown in this specification.

[0736] When comparing the results of Examples 1 to 6 of the present invention with the results of Comparative Examples 1C to 4C (which include examples taken from the prior art, in particular examples from US 3329674 (Example 3C herein)), it is clear that only the particles of the present invention (and the aqueous dispersions of the present invention) are capable of providing an aqueous dispersion containing an organic compound with an aziridine ring, said aqueous dispersion having enhanced storage stability at elevated temperatures for an extended period (4 weeks at 50 °C) and, at the same time, maintaining at least good crosslinking efficiency.

Claims

1. A particle comprising an (aziridinylhydroxy)-functional organic component, abbreviated as the AZ component, wherein the particle has an average hydrodynamic diameter based on scattering intensity of at least 30 nm and at most 1000 nm as determined by dynamic light scattering, abbreviated as D H , and wherein the AZ component is selected from the group consisting of the following i) to vi): i) an (aziridinylhydroxy)-functional organic compound AZ1 of formula A1 having only two aziridine rings, abbreviated as the AZ1 compound, ii) an (aziridinylhydroxy)-functional organic compound AZ2 of formula A2 having only three aziridine rings, abbreviated as the AZ2 compound, iii) an (aziridinylhydroxy)-functional organic compound AZ3 of formula A3 having only four aziridine rings, abbreviated as the AZ3 compound, iv) an (aziridinylhydroxy)-functional organic compound AZ4 of formula A4 having only five aziridine rings, abbreviated as the AZ4 compound, v) an (aziridinylhydroxy)-functional organic compound AZ5 of formula A5 having only six aziridine rings, abbreviated as the AZ5 compound, and vi) mixtures thereof, Wherein X1 is a divalent aliphatic organic group or a divalent aromatic organic group; X2 is a trivalent aliphatic organic group or a trivalent aromatic organic group; X3 is a tetravalent aliphatic organic group or a tetravalent aromatic organic group; X4 is a pentavalent aliphatic organic group or a pentavalent aromatic organic group; X5 is a hexavalent aliphatic organic group or a hexavalent aromatic organic group; and wherein each of said X1 to X5 consists of a set of atoms covalently linked in a configuration comprising a straight-chain and / or branched-chain and / or cyclic structure, said set of atoms being selected from the group consisting of the following i) to x): i) carbon and hydrogen atoms, ii) carbon, hydrogen and oxygen atoms, iii) carbon, hydrogen and nitrogen atoms, iv) carbon, hydrogen and sulfur atoms, v) carbon, hydrogen, oxygen and nitrogen atoms, vi) carbon, hydrogen, nitrogen and sulfur atoms, vii) carbon, hydrogen, oxygen and sulfur atoms, viii) carbon, hydrogen, oxygen, nitrogen and sulfur atoms, ix) carbon, hydrogen and silicon atoms, and x) carbon, hydrogen, oxygen and silicon atoms, and xi) any combination of ix) and / or x) with any one or all of iii) to viii), and wherein each of said X1 to X5 has carbon atoms and hydrogen atoms, and wherein each of said X1 to X5 optionally has oxygen atoms and / or nitrogen atoms and / or sulfur atoms and / or silicon atoms, and wherein said X1 and / or said X2 and / or said X3 and / or said X4 and / or said X5 optionally contains ionic functional groups, and wherein each of said X1 to X5 contains only single covalent bonds, or both single covalent bonds and double covalent bonds, and wherein said single covalent bonds are selected from the group consisting of: carbon-carbon single bonds, carbon-hydrogen single bonds, carbon-nitrogen single bonds, carbon-sulfur single bonds, carbon-silicon single bonds, silicon-oxygen single bonds, nitrogen-hydrogen single bonds, carbon-oxygen single bonds where oxygen is bonded to hydrogen to form a hydroxyl group, silicon-oxygen-silicon single bonds, and wherein said double covalent bonds are selected from the group consisting of: carbon-carbon double bonds, carbon-nitrogen double bonds and carbon-oxygen double bonds, and wherein Y is a monovalent organic group selected from the group consisting of: i) a monovalent aziridinyl hydroxyisopropyl organic group of formula B1, ii) a monovalent aziridinyl hydroxycyclohexane organic group of formula B2, and iii) a monovalent aziridinyl hydroxycyclohexane organic group of formula B3, and wherein R1 is selected from the group consisting of: hydrogen and methyl; and R2 is selected from the group consisting of: hydrogen, methyl and C2-C5 alkyl; and R3 is selected from the group consisting of: methyl and C2-C4 alkyl; and R4 is selected from the group consisting of: hydrogen, methyl and C2-C4 alkyl; and wherein the Ys in each of said compounds A1 to A5 are the same or different from each other, and wherein each of the single covalent bonds between said Y and each of said X1 to X5 is selected from the group consisting of: carbon-carbon single bonds, carbon-oxygen single bonds and carbon-nitrogen single bonds, and wherein each of said compounds AZ1 to AZ5 has a molecular weight of at least 600 Da and at most 5000 Da as determined by MALDI-TOF MS.

2. The particle according to claim 1, wherein the X1 is a divalent aliphatic organic group or a divalent aromatic organic group that is different from the divalent group of bisphenol A.

3. The particle according to any one of claims 1 to 2, wherein the X1 and / or the X2 and / or the X3 and / or the X4 and / or the X5 comprises at least one structural unit or a combination of structural units selected from the group consisting of: Unit 1, Unit 2, Unit 3, Unit 4, Unit 5, Unit 6, Unit 7, Unit 8, Unit 9, Unit 10, and Unit 11, wherein Units 1 to 11 are depicted as follows: Wherein R' is selected from the group consisting of: hydrogen and methyl; and j is an integer in the range from 1 to 5; and n is an integer in the range from and including 2 up to and including 50.

4. The particle according to any one of claims 1 to 2, wherein the aggregation number of carbon atoms in R1, R2, R3, and R4 is at most 9.

5. The particle according to any one of claims 1 to 2, wherein the X1 and / or the X2 and / or the X3 and / or the X4 and / or the X5 does not contain one or any combination of the following structural units BP1, BP2, BP3, and BS 6. The particle according to any one of claims 1 to 2, wherein the X1 is a divalent aliphatic organic group of formula A1a' Wherein R' is selected from the group consisting of: hydrogen and methyl; and j is an integer in the range from 1 to 5; and n is an integer in the range from and including 2 up to and including 50.

7. The particle according to any one of claims 1 to 2, wherein the AZ component is selected from the group consisting of the following i) to v): i) AZ1 compound, ii) AZ2 compound, iii) AZ3 compound, iv) AZ5 compound, and vi) their mixtures, and Wherein The AZ1 compound is selected from the group consisting of: a compound having formula A1a and a compound having formula A1b, each of these formulas A1a - A1d is described as follows Wherein each of the n's in formula A1a is independently selected, and each of the n's in formula A1a is an integer in the range from and including 2 up to and including 20; and wherein R in formula A1b is a C3-C 10 saturated alkylene group, and each of said n's in formula A1b is independently selected, and each of said n's in formula A1a is an integer in the range from and including 2 up to and including 20; and Wherein each of the n's in formula A1c is independently selected, and each of the n's in formula A1b is an integer in the range from and including 2 up to and including 20; and wherein R in formula A1d is a C3-C 10 saturated alkylene group, and wherein each of said n in formula A1d is independently selected, and each of said n in formula A1b is an integer in the range from and including 2 up to and including 20; and Wherein The AZ2 compound is selected from the group consisting of: a compound having formula A2a, a compound having formula A2b, a compound having formula A2c, a compound having formula A2d, a compound having formula A2e, each of these formulas A2a - A2e is described below Wherein n in formula A2a is an integer in the range from and including 2 up to and including 20; And Wherein each of the n's in formula A2b is independently selected, and each of the n's in formula A2b is an integer in the range from and including 2 up to and including 20; and Each n in formula A2c is independently selected, and each of the ns in formula A2c is an integer in the range from and including 2 up to and including 20; and and and wherein the AZ3 compound is selected from the group consisting of compounds having formula A3a wherein each of the ns in formula A3a is independently selected, and each of the ns in formula A3a is an integer in the range from and including 2 up to and including 20; and wherein the AZ5 compound is selected from the group consisting of compounds having formula A5a wherein each of the ns in formula A5a is independently selected, and each of the ns in formula A5a is an integer in the range from and including 2 up to and including 40.

8. The particle according to any one of claims 1 to 2, wherein the AZ component is selected from the group consisting of AZ1 compounds, and wherein the AZ1 compound is a compound of the following formula, 9. The particle according to any one of claims 1 to 2, wherein the AZ component is selected from the group consisting of AZ2 compounds, and wherein the AZ2 compound is a compound of the following formula, 10. The particle according to any one of claims 1 to 2, wherein the AZ component is selected from the group consisting of AZ2 compounds, and wherein the AZ2 compound is a compound of the following formula, 11. The particle according to any one of claims 1 to 2, wherein the AZ component is selected from the group consisting of AZ2 compounds, and wherein the AZ2 compound is a compound of the following formula, 12. The particle according to any one of claims 1 to 2, wherein the AZ component is selected from the group consisting of AZ1 compounds, AZ2 compounds or mixtures thereof, and wherein the AZ1 compound is a compound of the following formula, and wherein the AZ2 compound is selected from the group consisting of compounds of the following formula 13. An aqueous dispersion having a pH of at least 7.5 and at most 14.0 as measured according to ISO 976:2013, and wherein the aqueous dispersion comprises: i) water, and ii) the particles according to any one of claims 1 - 12, the particles being dispersed in the water.

14. A particle obtained by a method comprising the following steps: i) providing the aqueous dispersion according to claim 13; and ii) removing the water and any organic solvent present, if any, from the aqueous dispersion to obtain the particles; and iii) collecting the particles, and iv) optionally further drying the particles; and v) optionally applying means that convert the collected particles into any form in which the solid material exists under standard conditions.

15. An aqueous composition comprising: i) the aqueous dispersion according to claim 13, and ii) a polymer having an acid value in the range of 5 mg KOH / g to 300 mg KOH / g as measured according to ASTM D1639 - 90(1996)e1, and wherein the polymer optionally contains ionic functional groups.

16. A parts kit, the parts kit comprising physically separate parts A and parts B, wherein: i) part A contains the aqueous dispersion according to claim 13, and ii) part B contains a polymer having an acid value in the range of 5 mg KOH / g to 300 mg KOH / g as determined according to ASTM D1639-90(1996)e1, and wherein the polymer optionally contains ionic functional groups, and wherein part A does not contain the polymer of part B, and part B does not contain the aqueous dispersion of part A.

17. A cured form of any of the following: i) the particles according to any one of claims 1-12, or ii) the aqueous dispersion according to claim 13, or iii) the particles according to claim 14, or iv) the aqueous composition according to claim 15.

18. An article selected from the group consisting of textiles, glass, metal, composites, plastics, wood, engineered wood, wood substitutes, leather, artificial leather, paper, fibers, wherein the article comprises: i) the particles according to any one of claims 1-12, and / or ii) the aqueous dispersion according to claim 13, and / or iii) the particles according to claim 14, and / or iv) the aqueous composition according to claim 15, and / or v) the cured form according to claim 17.

19. Use of any one or any combination of the following in coatings, paints, inks, varnishes, lubricants, adhesives, additive manufacturing, 3D printing, textiles, waxes, fuels, photography, plastics, medical compositions, medical devices: i) the particles according to any one of claims 1-12; ii) the aqueous dispersion according to claim 13; iii) the particles according to claim 14; iv) the aqueous composition according to claim 15; v) the parts kit according to claim 16; vi) the cured form according to claim 17; vii) the article according to claim 18.

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