(Aziridinylhydroxy)-functionalized organic compound

Abstract

The present invention relates to a specific (aziridinylhydroxy)-functional organic component. The present invention also relates to a liquid composition comprising the (aziridinylhydroxy)-functional organic component. The present invention also relates to a coating composition comprising the (aziridinylhydroxy)-functional organic component. The present invention also relates to a liquid coating composition comprising the (aziridinylhydroxy)-functional organic component. The present invention also relates to a parts kit comprising an aqueous dispersion containing the specific (aziridinylhydroxy)-functional organic component in one of its parts. The present invention also relates to the liquid composition, the coating composition, and the cured form of the liquid coating composition. The present invention also relates to an article comprising the (aziridinylhydroxy)-functional organic component and / or the liquid composition and / or the liquid coating composition and / or their cured forms. The present invention also relates to various uses of the (aziridinylhydroxy)-functional organic component and / or the liquid composition and / or the liquid coating composition and / or the parts kit and / or the cured form.

Description

[0001] The present invention relates to a specific (aziridinylhydroxy)-functional organic component. The present invention also relates to a liquid composition comprising the (aziridinylhydroxy)-functional organic component. The present invention also relates to a coating composition comprising the (aziridinylhydroxy)-functional organic component. The present invention also relates to a liquid coating composition comprising the (aziridinylhydroxy)-functional organic component. The present invention also relates to a parts kit comprising a liquid composition containing the specific (aziridinylhydroxy)-functional organic component in one of its parts. The present invention also relates to the liquid composition, the coating composition and the cured form of the liquid coating composition. The present invention also relates to an article comprising the (aziridinylhydroxy)-functional organic component and / or the liquid composition and / or the liquid coating composition and / or their cured forms. The present invention also relates to various uses of the (aziridinylhydroxy)-functional organic component and / or the liquid composition and / or the liquid coating composition and / or the parts kit and / or the cured form.

[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 extremely reactive compounds and attractive for various industrial applications. However, several organic compounds bearing an aziridine ring exhibit unfavorable genotoxicity characteristics, which means that several organic compounds bearing an aziridine ring exhibit positive induced genotoxicity - as that term is defined and determined in the specification. For example, trimethylolpropane tris(2-methyl-1-aziridine propionate) (CAS No.: 64265-57-2; available from DSM as 'crosslinker CX-100') and pentaerythritol tris[3-(1-aziridinyl)propionate (CAS No.: 57116-45-7; available from Ichemco as

[0014] In the United States, polyfunctional aziridine crosslinkers have been used to crosslink carboxylic acid-functional polymers, including trimethylolpropane tris(2-methyl-1-aziridine propionate) (available commercially from Aziridines, CAS No. 57116-45-7) and pentaerythritol tris(3-(1-aziridinyl)propionate) (CAS No. 57116-45-7, available commercially from LLC Aziridines as PZ-33). However, trimethylolpropane tris(2-methyl-1-aziridine propionate) has an unfavorable genotoxicity profile, as it exhibits positive induction of genotoxicity. Therefore, in view of the desire and need imposed by various national regulatory systems on various industries to improve the safety, health and environmental status of their products (e.g., adhesives, inks and coatings) and the raw materials (e.g., compounds bearing an aziridine ring) used to prepare said products, such as adhesives, inks and coatings, for example, the use of organic compounds bearing an aziridine ring is restricted.

[0003] In genetics, genotoxicity describes the property of chemical or physical agents that cause any type of damage to DNA within cells, leading to mutations that may, for example, cause cancer. Damage to DNA may not always result in transmissible mutations. Genotoxicity should not be confused with mutagenicity; all mutagens are genotoxic, but not all genotoxic agents are mutagenic. Mutagenicity refers to the induction of permanent and transmissible changes in DNA (such as DNA composition or chromosome structure) that are retained in dividing somatic cells and passed on to subsequent generations of germ cells.

[0004] US 2007 / 298006 A1 (equivalent to WO 2006 / 115547 A2) to Dendritic Nanotechnologies, PLLC discloses dendrimers with enhanced amplification and internal functionality. Example 12 of US 2007 / 298006 A1 discloses a compound bearing an aziridine ring. This compound is the only aziridine ring-bearing compound disclosed in US 2007 / 298006 A1. The compound of Example 12 of US 2007 / 298006 A1 is obtained as a clear, colorless oil with a molecular weight of 588 Da and is used as a synthetic intermediate in the preparation of dendrimers (via aziridine ring opening reaction). US 2007 / 298006 A1 does not disclose (aziridinylhydroxy)-functional organic components with a molecular weight of at least 600 Da and up to 10,000 Da. US 2007 / 298006 A1 is silent on (aziridinylhydroxy)-functional organic components (and liquid compositions thereof) which do not combine with genotoxicity and have a good, preferably very good, more preferably excellent, crosslinking efficiency.

[0005] US Pat. No. 3,329,674 to Thiokol Chemical Corporation discloses low molecular weight aziridinyl compounds. The molecular weights of these aziridinyl compounds are well below 600 Da (see Examples 1-7; the molecular weights of these compounds range from 304 to 526). US Pat. No. 3,329,674 discloses (aziridinylhydroxy)-functional organic compounds having molecular weights of at least 600 and up to 10,000 Da. US Pat. No. 3,329,674 mentions (aziridinylhydroxy)-functional organic components (and liquid compositions thereof) that do not exhibit genotoxicity and have good, preferably very good, and more preferably excellent crosslinking efficiency.

[0006] EP 1865014 A1 from 3M Innovative Properties Company discloses compositions comprising a prepolymer as component (A), wherein the prepolymer comprises an aziridine group. On pages 8-14 (compounds 1 to 10), EP 1865014 A1 discloses compounds bearing aziridine groups. However, these compounds—at least—do not have a hydroxyl group attached to a β-carbon atom attached to the nitrogen atom of the aziridine group. In addition, compounds 1, 2, 3, 4, 9, and 10 have an ester group attached to the aforementioned β-carbon atom, while compounds 5, 6, 7, and 8 have a methyl group attached to the aforementioned β-carbon atom. Thus, EP 1865014 A1 discloses very different compounds bearing aziridine groups. EP 1865014 A1 not only discloses very different compounds bearing aziridine groups, but also does not disclose (aziridine hydroxyl)-functional organic compounds having a molecular weight of at least 600 and at most 10,000 Da. EP 1865014 A1 is silent on (aziridinylhydroxy)-functional organic components (and liquid compositions thereof) which do not combine with genotoxicity and have a good, preferably very good, more preferably excellent, crosslinking efficiency.

[0007] WO 2015 / 066868 A1 from 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 the β-carbon atom attached to the nitrogen atom of the aziridine group. Therefore, WO 2015 / 066868 A1 discloses very different compounds bearing aziridine groups. Thus, WO 2015 / 066868 A1 not only discloses very different compounds bearing aziridine groups, but also fails to disclose (aziridine hydroxyl)-functional organic compounds having a molecular weight of at least 600 and at most 10,000 Da. WO 2015 / 066868 A1 does not mention (aziridine hydroxyl)-functional organic components (and liquid compositions thereof) that are non-genotoxic and have good, preferably very good, and more preferably excellent crosslinking efficiency.

[0008] EP 0758662 A2 from Rockwell International Corporation discloses a curable resin system comprising an epoxy resin, a coreactant selected from N-alkyl and N-aryl substituted aziridines, and a catalyst that promotes curing at ambient temperature. In Example 3, EP 0758662 A2 discloses the reaction of PY 306 epoxy resin with 2-methylaziridine 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, sections 1.5, 1.59 to 1.6, 1.1). The aziridine-terminated organic compound is obtained as a viscous liquid and has a molecular weight of 426.25 Da (calculated based on the stoichiometrics of the reactants disclosed in the first sentence of Example 3 of EP 0758662 A2), and is used as a synthetic intermediate. EP 0758662 A2 does not disclose (aziridinylhydroxy)-functional organic compounds having a molecular weight of at least 600 and at most 10,000 Da. EP 0758662 A2 does not mention (aziridinylhydroxy)-functional organic components (and liquid compositions thereof) that do not combine with genotoxicity and have good, preferably very good, and more preferably excellent crosslinking efficiency.

[0009] In order to enable wider use of organic compounds bearing an aziridine ring, which are generally attractive for a variety of potential industrial applications, without compromising the safety, health and environmental aspects of processes and products in which organic compounds bearing an aziridine ring are or can be used, it is desirable to provide organic compounds bearing an aziridine ring which are not genotoxic and have good, preferably very good, more preferably excellent, cross-linking efficiency.

[0010] However, the aforementioned aspirations still represent an unmet need, as approaches to address such issues are particularly challenging given their rather unfavorable genotoxic profile and the general bias against their use in industrial applications due to their known adverse genotoxic profile.

[0011] Therefore, the object of the present invention is to provide a solution to the above unmet needs. In other words, the object of the present invention is to provide organic compounds with an aziridine ring which are non-genotoxic and have good, preferably very good, more preferably excellent cross-linking efficiency.

[0012] This object is surprisingly achieved by specific (aziridinylhydroxy)-functional organic compounds as disclosed in the description, which form (aziridinylhydroxy)-functional organic components (abbreviated to "AZ-components").

[0013] More specifically, the AZ-component (and liquid composition comprising the AZ-component) is not genotoxic and has a good, preferably very good, more preferably excellent cross-linking efficiency.

[0014] AZ-components (and liquid compositions containing AZ-components) constitute a significant technological advancement for several industries that require or currently use highly reactive reagents such as compounds bearing an aziridine ring. The reason is that the AZ-components provide these industries with a real opportunity not only to pursue new synthetic or application pathways for new and innovative products and processes, but also to significantly improve the safety, health and environmental profile of their operations, products and processes.

[0015] Broadly according to the present invention there is provided an AZ component as disclosed in the specification.

[0016] Broadly according to the present invention there is provided a liquid composition as disclosed in the specification.

[0017] Broadly according to the present invention, there is provided a kit of parts as disclosed in the specification.

[0018] Broadly according to the present invention there is provided a cured form as disclosed in the specification.

[0019] Broadly according to the present invention there is provided an article as disclosed in the specification.

[0020] Broadly, according to the present invention, there is provided the use of any one or any combination of the following as a cross-linking agent:

[0021] i) AZ-components according to any one of A1 to A18 and disclosed throughout the specification;

[0022] ii) A liquid composition according to any one of A19 to A34 and as disclosed throughout the specification.

[0023] 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:

[0024] i) AZ-components according to any one of A1 to A18 and disclosed throughout the specification;

[0025] ii) a liquid composition according to any one of A19 to A34 and as disclosed throughout the specification;

[0026] iii) a kit of parts according to A35 and as disclosed throughout this specification;

[0027] iv) a cured form according to any one of A36 to A37 and as disclosed throughout the specification;

[0028] v) An article according to any one of A38 to A39 and as disclosed throughout the specification.

[0029] A1a Broadly, according to the present invention, there is provided an (aziridinylhydroxy)-functional organic component (AZ-component) as disclosed in the specification.

[0030] The following paragraphs A1 to A41 constitute certain specific preferences for the Az-component according to A1a and certain further specific aspects of the invention according to the AZ-component according to A1a. More specifically, preferences for the AZ-component according to A1a include, but are not limited to, preferences A1 to A18, while aspects of the invention according to the AZ-component according to A1a include, but are not limited to, aspects A19 to A41. Many other variations, combinations, or embodiments of the invention will be apparent to those skilled in the art, and such variations, combinations, and embodiments are contemplated to be within the scope of the claimed invention. The antecedent basis for certain terms shown in the preferences and aspects can be found in the preceding preferences or aspects. Any reference to components includes their preferences and preferred ranges disclosed throughout this specification.

[0031] A1 An (aziridinylhydroxy)-functional organic component (AZ-component) according to A1a or any combination of the disclosure from subsection 1 and the entire specification, 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 A5 having only five aziridine rings; v) an (aziridinylhydroxy)-functional organic compound AZ5 (AZ5 compound) of formula A5 having only six aziridine rings; and vi) a mixture thereof, preferably the AZ component is selected from the group consisting of the following i) to iv): i) an (aziridinylhydroxy)-functional organic compound AZ1 (AZ1 compound) of formula A1 having only two aziridine rings; ii) an (aziridinylhydroxy)-functional organic compound AZ2 (AZ2 compound) of formula A2 having only three aziridine rings; iii) an (aziridinylhydroxy)-functional organic compound AZ3 (AZ3 compound) of formula A3 having only four aziridine rings; and iv) a mixture thereof,

[0032]

[0033] in

[0034] X1 is a divalent aliphatic organic group or a divalent aromatic organic group, preferably X1 is a divalent aliphatic organic group;

[0035] X2 is a trivalent aliphatic organic group or a trivalent aromatic organic group, preferably X2 is a trivalent aliphatic organic group;

[0036] X3 is a tetravalent aliphatic organic group or a tetravalent aromatic organic group, preferably X3 is a tetravalent aliphatic organic group;

[0037] X4 is a pentavalent aliphatic organic group or a pentavalent aromatic organic group, preferably X4 is a pentavalent aliphatic organic group;

[0038] X5 is a hexavalent aliphatic organic group or a hexavalent aromatic organic group, preferably X5 is a hexavalent aliphatic organic group;

[0039] and wherein each of said X1 to X5 consists of a collection of atoms covalently linked in a configuration comprising linear and / or branched and / or cyclic structures, preferably consisting of linear and / or branched and / or cyclic structures, said collection 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 viiii),

[0040] and wherein each of said X1 to X5 has a carbon atom and a hydrogen atom,

[0041] and wherein each of said X1 to X5 optionally has an oxygen atom and / or a nitrogen atom and / or a sulfur atom and / or a silicon atom,

[0042] and wherein X1 and / or X2 and / or X3 and / or X4 and / or X5 may optionally contain an ionic functional group, preferably X1 and / or X2 and / or X3 and / or X4 and / or X5 do not contain an ionic functional group,

[0043] And among them

[0044] 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,

[0045]

[0046] And among them

[0047] R1 is selected from the group consisting of: hydrogen and methyl; and

[0048] R2 is selected from the group consisting of hydrogen, methyl and C2-C5 alkyl; and

[0049] R3 is selected from the group consisting of: methyl and C2-C4 alkyl; and

[0050] R4 is selected from the group consisting of hydrogen, methyl and C2-C4 alkyl;

[0051] And among them

[0052] 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 the Y and each of the X1 to X5 is selected from the group consisting of a carbon-carbon single bond, a carbon-oxygen single bond and a carbon-nitrogen single bond, preferably a carbon-oxygen single bond and a carbon-nitrogen single bond, more preferably a carbon-oxygen single bond,

[0053] And among them

[0054] Each of compounds AZ1 to AZ5 has a molecular weight of at least 600 Da and at most 10000 Da, preferably at least 600 Da and at most 8000 Da, more preferably at least 600 Da and at most 7000 Da, even more preferably at least 600 Da and at most 6000 Da, for example at least 600 Da and at most 5500 Da, for example at least 600 Da and at most 5000 Da, for example at least 600 Da and at most 4000 Da, for example at least 600 Da and at most 3500 Da, for example at least 600 Da and at most 3200 Da, for example at least 600 Da and at most 3000 Da, for example at least 600 Da and at most 2500 Da, for example at least 600 Da and at most 220 0 Da, for example at least 600 Da and at most 2000 Da, for example at least 630 Da and at most 10000 Da, for example at least 630 Da and at most 8000 Da, for example at least 630 Da and at most 7000 Da, for example at least 630 Da and at most 6000 Da, for example at least 630 Da and at most 5500 Da, for example at least 630 Da and at most 5000 Da, for example at least 630 Da and at most 4000 Da, for example at least 630 Da and at most 3500 Da, for example at least 630 Da and at most 3200 Da, for example at least 630 Da and at most 3000 Da, for example at least 630 Da and at most 2500 Da, for example at least 630 Da and at most 3500 Da, 630 Da and at most 2200 Da, for example at least 630 Da and at most 2000 Da, for example at least 640 Da and at most 10000 Da, for example at least 640 Da and at most 8000 Da, for example at least 640 Da and at most 7000 Da, for example at least 640 Da and at most 6000 Da, for example at least 640 Da and at most 5500 Da, for example at least 640 Da and at most 5000 Da, for example at least 640 Da and at most 4000 Da, for example at least 640 Da and at most 3500 Da, for example at least 640 Da and at most 3200 Da, for example at least 640 Da and at most 3000 Da, for example at least 640 Da and at most 640 Da. 2500 Da, for example at least 640 Da and at most 2200 Da, for example at least 640 Da and at most 2000 Da, for example at least 650 Da and at most 10000 Da, for example at least 650 Da and at most 8000 Da, for example at least 650 Da and at most 7000 Da, for example at least 650 Da and at most 6000 Da, for example at least 650 Da and at most 5500 Da, for example at least 650 Da and at most 5000 Da, for example at least 650 Da and at most 4000 Da, for example at least 650 Da and at most 3500 Da, for example at least 650 Da and at most 3200 Da, for example at least 650 Da and at most 3000 Da,For example at least 650 Da and at most 2500 Da, for example at least 650 Da and at most 2200 Da, for example at least 650 Da and at most 2000 Da, for example at least 700 Da and at most 10000 Da, for example at least 700 Da and at most 8000 Da, for example at least 700 Da and at most 7000 Da, for example at least 700 Da and at most 6000 Da, for example at least 700 Da and at most 5500 Da, for example at least 700 Da and at most 5000 Da, for example at least 700 Da and at most 4000 Da, for example at least 700 Da and at most 3500 Da, for example at least 700 Da and at most 3200 Da, for example at least 700 Da and at most 3000 Da, For example at least 700 Da and at most 2500 Da, for example at least 700 Da and at most 2200 Da, for example at least 700 Da and at most 2000 Da, for example at least 750 Da and at most 10000 Da, for example at least 750 Da and at most 8000 Da, for example at least 750 Da and at most 7000 Da, for example at least 750 Da and at most 6000 Da, for example at least 750 Da and at most 5500 Da, for example at least 750 Da and at most 5000 Da, for example at least 750 Da and at most 4000 Da, for example at least 750 Da and at most 3500 Da, for example at least 750 Da and at most 3200 Da, for example at least 750 Da and at most 3000 Da, For example at least 750 Da and at most 2500 Da, for example at least 750 Da and at most 2200 Da, for example at least 750 Da and at most 2000 Da, for example at least 800 Da and at most 10000 Da, for example at least 800 Da and at most 8000 Da, for example at least 800 Da and at most 7000 Da, for example at least 800 Da and at most 6000 Da, for example at least 800 Da and at most 5500 Da, for example at least 800 Da and at most 5000 Da, for example at least 800 Da and at most 4000 Da, for example at least 800 Da and at most 3500 Da, for example at least 800 Da and at most 3200 Da, for example at least 800 Da and at most 3000 Da, For example, at least 800 Da and at most 2500 Da, for example, at least 800 Da and at most 2200 Da, for example, at least 800 Da and at most 2000 Da, for example, at least 850 Da and at most 10000 Da, for example, at least 850 Da and at most 8000 Da, for example, at least 850 Da and at most 7000 Da, for example, at least 850 Da and at most 6000 Da, for example, at least 850 Da and at most 5500 Da, for example, at least 850 Da and at most 5000 Da, for example, at least 850 Da and at most 4000 Da, for example, at least 850 Da and at most 3500 Da, for example, at least 850 Da and at most 3200 Da, for example, at least 850 Da and at most 3000 Da,For 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 Such as 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 1 1000 Da and at most 8000 Da, for example at least 1100 Da and at most 9000 Da, for example at least 1100 Da and at most 1200 Da, for example at least 1100 Da and at most 1300 Da, for example at least 1100 Da and at most 14000 Da, for example at least 1100 Da and at most 1500 Da, for example at least 1100 Da and at most 16000 Da, for example at least 1100 Da and at most 17000 Da, for example at least 1100 Da and at most 18000 Da, for example at least 1100 Da and at most 2000 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 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 8000 Da. A molecular weight of 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.

[0055] A2 An AZ-component according to any of A1a or A1 or any combination of the disclosure from subsection 1 and the entire specification, wherein X1 is a divalent aliphatic organic radical or a divalent aromatic organic radical other than the divalent radical of bisphenol A.

[0056] A3 An AZ-component 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 X1 is a divalent aliphatic organic group or a divalent aromatic organic group other than a divalent organic group selected from the group consisting of: a divalent group of bisphenol A, a divalent group of bisphenol AP, a divalent group of bisphenol AF, a divalent group of bisphenol B, a divalent group of bisphenol BP, a divalent group of bisphenol C, a divalent group of bisphenol C2, a divalent group of bisphenol E, a divalent group of bisphenol F, a divalent group of bisphenol G, a divalent group of bisphenol M, a divalent group of bisphenol S, a divalent group of bisphenol P, a divalent group of bisphenol PH, a divalent group of bisphenol TMC, a divalent group of bisphenol Z, a divalent group of dinitrobisphenol A, a divalent group of tetrabromobisphenol A, and combinations thereof, preferably X1 is a divalent aliphatic organic group.

[0057] A4 An AZ-component according to any one of A1a or A1 to A3 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 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, preferably comprises at least one structural unit or a 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 being depicted below:

[0058]

[0059] in

[0060] R' is selected from the group consisting of: hydrogen and methyl; and

[0061] j is an integer ranging from 1 to 5, preferably from 1 to 3; and

[0062] n is in the range of 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 (for example 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 (for example 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 (for example, 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 (for example, n is 5), for example, from and including 6 up to and including 50, for example, from and including 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 (for example, 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 (for example, 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 10 Integers including 20, for example, from and including 8 up to and including 15, for example, from and including 8 up to and including 10 (for example, 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 (for example, 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 (for example, n is 10).

[0063] A5 An AZ-component according to A1a or any one of A1 to A4 or any combination of the disclosure from subsection 1 and the entire specification, wherein

[0064] R1 is selected from the group consisting of: hydrogen and methyl; and

[0065] R2 is selected from the group consisting of: hydrogen, methyl and ethyl; and

[0066] R3 is selected from the group consisting of: methyl and C2-C4 alkyl; and

[0067] R4 is selected from the group consisting of hydrogen, methyl and ethyl.

[0068] A6 An AZ-component according to any one of A1a or A1 to A5 or any combination derived from the disclosure in subsection 1 and the entire specification, wherein the aggregate 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.

[0069] A7 An AZ-component according to A1a or any one of A1 to A6 or any combination of the disclosure from subsection 1 and the entire specification, wherein X1 and / or X2 and / or X3 and / or X4 and / or X5 does not comprise one or any combination of the following structural units BP1, BP2, BP3 and BS

[0070]

[0071]

[0072] A8 An AZ-component according to A1a or any one of A1 to A8 or any combination of the disclosure from subsection 1 and the entire specification, wherein X1 and / or X2 and / or X3 and / or X4 and / or X5 comprises at least one unit 11 as a structural unit.

[0073] A10 An AZ-component according to A1a or any one of A1 to A8 or any combination thereof derived from the disclosure in subsection 1 and the entire specification, wherein X1 is a divalent aliphatic organic group of formula A1a'

[0074]

[0075] in

[0076] R' is selected from the group consisting of: hydrogen and methyl; and

[0077] j is an integer ranging from 1 to 5, preferably from 1 to 3; and

[0078] n is in the range of 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 (for example 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 (for example 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 (for example, 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 (for example, n is 5), for example, from and including 6 up to and including 50, for example, from and including 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 (for example, 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 (for example, 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 10 Integers including 20, for example, from and including 8 up to and including 15, for example, from and including 8 up to and including 10 (for example, 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 (for example, 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 (for example, n is 10).

[0079] A10 An AZ-component according to A1a or any one of A1 to A9 or any combination of the disclosure from subsection 1 and the entire specification, wherein each of X1 to X5 comprises only single covalent bonds, or both single and double covalent bonds, and wherein the single covalent bond is selected from the group consisting of a carbon-carbon single bond, a carbon-hydrogen single bond, a carbon-nitrogen single bond, a carbon-sulfur single bond, a carbon-silicon single bond, a silicon-oxygen single bond, a nitrogen-hydrogen single bond, a sulfur-oxygen single bond, a carbon-oxygen single bond in which oxygen is bonded to hydrogen to form a hydroxyl group, a silicon-oxygen-silicon single bond, and wherein the double covalent bond is selected from the group consisting of a carbon-carbon double bond, a carbon-nitrogen double bond, a sulfur-oxygen double bond, a carbon-oxygen double bond in which carbon is a member of a ring structure, and a carbon-oxygen double bond in which the carbon is bonded to two other carbons via a carbon-carbon single bond, a carbon-oxygen double bond in which the carbon is bonded to another oxygen via a single bond and to a nitrogen via a single bond, a carbon-oxygen double bond in which the carbon is bonded to two nitrogens via a carbon-nitrogen single bond, a carbon-oxygen double bond in which the carbon is bonded to two other oxygens via a single bond, preferably, the double covalent bond is selected from the group consisting of a carbon-carbon double bond, a carbon-nitrogen double bond, a sulfur-oxygen double bond, a carbon-oxygen double bond in which the carbon is a member of a ring structure, and a carbon-oxygen double bond in which the carbon is bonded to two other carbons via a carbon-carbon single bond, a carbon-oxygen double bond in which the carbon is bonded to another oxygen via a single bond and to a nitrogen via a single bond, a carbon-oxygen double bond in which the carbon is bonded to two nitrogens via a carbon-nitrogen single bond.

[0080] A11 An AZ-component according to any one of A1a or A1 to A10 or any combination of the disclosure from subsection 1 and the entire specification, wherein the aggregation number of carbon atoms and hydrogen atoms in X1 and / or X2 and / or X3 and / or X4 and / or X5, relative to the aggregation number of all atoms present in X1 and / or X2 and / or X3 and / or X4 and / or X5, respectively, is at least 5%, preferably at least 10%, more preferably at least 15%, most preferably at least 20%, such as at least 25%, such as at least 30%, such as at least 35%, such as at least 40%, such as at least 45%, such as at least 50%, such as at least 55%, such as at least 60%, such as at least 65%, such as at least 70%, such as at least 75%, such as at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 97%, such as at least 98%, such as at least 99%, such as 100%.

[0081] A12 An AZ-component according to A1a or any one of A1 to A11 or any combination of the disclosure from subsection 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.

[0082] A13 An AZ-component according to any one of A1a or A1 to A12 or any combination of the disclosure from subsection 1 and the entire specification, wherein the AZ component is selected from the group consisting of: i) an (aziridinylhydroxy)-functional organic compound AZ1 of formula A1 (AZ1 compound), ii) an (aziridinylhydroxy)-functional organic compound AZ2 of formula A2 (AZ2 compound), iii) an (aziridinylhydroxy)-functional organic compound AZ3 of formula A3 (AZ3 compound), iv) an (aziridinylhydroxy)-functional organic compound AZ5 of formula A5 (AZ5 compound), and vi) a mixture thereof, and

[0083] in

[0084] 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 as follows

[0085]

[0086] 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, 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 is equal to 4); and

[0087]

[0088] Wherein R in formula A1b is C3-C 10 saturated alkylene, 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 is equal to 4);

[0089]

[0090] 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 is equal to 4), and

[0091]

[0092] Wherein R in formula A1d is C3-C 10 saturated alkylene, 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 is equal to 4); and

[0093] in

[0094] 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 which is described below.

[0095]

[0096] wherein n in Formula A2a is an integer ranging from and including 2 up to and including 20, for example, from and including 2 up to and including 10, for example, from and including 2 up to and including 8, 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 8, for example, from and including 4 up to and including 20, for example, from and including 4 up to and including 10, for example, from and including 4 up to and including 8, for example, from and including 5 up to and including 20, for example, from and including 5 up to and including 10, for example, from and including 5 up to and including 8, for example, from and including 6 up to and including 20, for example, from and including 6 up to and including 10, for example, from and including 6 up to and including 8 (for example, n is equal to 7);

[0097] and

[0098]

[0099] wherein each n in formula A2b is independently selected, and each n in formula A2b ranges 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 an integer 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 (for example n is equal to 11);

[0100] and

[0101]

[0102] wherein each n in formula A2c is independently selected, and each n in formula A2c ranges 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 an integer 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 (for example n is equal to 11);

[0103] and

[0104]

[0105] and

[0106] in

[0107] The AZ3 compound is selected from the group consisting of: a compound having formula A3a

[0108]

[0109] wherein 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 (for example n equals 3, for example n equals 2);

[0110] and

[0111] in

[0112] The AZ5 compound is selected from the group consisting of: a compound having formula A5a

[0113]

[0114] Formula A5a

[0115] wherein 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 (for example n equals 4, for example n equals 3).

[0116] A14 An AZ-component according to A1a or any one of A1 to A13 or any combination of the disclosure from subsection 1 and the entire specification, wherein

[0117] X1 and / or X2 and / or X3 and / or X4 and / or X5 do not contain any structural units of (or equivalently derived from) a phenol-formaldehyde resin (also known as a novolac 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 resol resins (base-catalyzed PF resins with a formaldehyde to phenol ratio greater than 1, typically equal to 1.5).

[0118] A15 An AZ-component according to any one of A1a or A1 to A14 or any 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 formula,

[0119]

[0120] A16 An AZ-component according to A1a or any one of A1 to A15 or any combination of the disclosure from subsection 1 and the entire specification, wherein

[0121] The AZ component is selected from the group consisting of: an AZ2 compound, and wherein the AZ2 compound is a compound of the formula,

[0122]

[0123] A17 An AZ-component according to any one of A1a or A1 to A19 or any combination of the disclosure from subsection 1 and the entire specification, wherein

[0124] The AZ component is selected from the group consisting of: an AZ2 compound, and wherein the AZ2 compound is a compound of the formula,

[0125]

[0126] A18 An AZ-component according to any one of A1a or A1 to A17 or any 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 formula,

[0127]

[0128] A19 A liquid composition according to any combination of the disclosure from subsections 1 and 3 and the entire specification, comprising:

[0129] i) a liquid medium selected from organic solvents, water and mixtures thereof in an amount of at most 90 wt.-%, preferably at most 85 wt.-%, more preferably at most 80 wt.-%, most preferably at most 75 wt.-%, such as at most 70 wt.-%, for example at most 65 wt.-%, for example at most 60 wt.-%, for example at most 55 wt.-%, for example at most 50 wt.-%, for example at most 45 wt.-%, for example at most 40 wt.-%, for example at most 35 wt.-%, for example at most 30 wt.-%, for example at most 25 wt.-%, for example at most 20 wt.-%, for example at most 15 wt.-%, for example at most 10 wt.-%, for example at most 5 wt.-%, for example at most 2 wt.-%, for example at most 1 wt.-%; e.g., the liquid composition contains no liquid medium; and

[0130] ii) an AZ component according to any one of A1a or A1 to A18 or any combination of the disclosure from subsections 1 and 3 and the entire specification; and

[0131] The total amount of all components constituting the liquid composition adds up to 100 wt%.

[0132] A20 A liquid composition according to A19 or any combination of the disclosure arising from subsections 1 and 3 and the entire specification, wherein the liquid composition comprises at most 90 wt.-%, preferably at most 85 wt.-%, more preferably at most 80 wt.-%, at most preferably at most 75 wt.-%, for example at most 70 wt.-%, for example at most 65 wt.-%, for example at most 60 wt.-%, for example at most 55 wt.-%, for example at most 50 wt.-%, for example at most 45 wt.-%, for example at most 40 wt.-%, for example at most 35 wt.-%, for example at most 30 wt.-%, for example at most 25 wt.-%, for example at most 20 wt.-%, for example at most 15 wt.-%, for example at most 10 wt.-%, for example at most 5 wt.-%, for example at most 2 wt.-%, for example at most 1 wt.-% water, based on the total weight of the liquid composition, for example the liquid composition does not contain water.

[0133] A21 A liquid composition according to any one of A14 to A20 or any combination of the disclosures in subsections 1 and 3 and the entire specification, wherein the liquid composition comprises water in an amount of at least 70 wt% and at most 90 wt%, preferably at least 75 wt% and at most 85 wt%, based on the total weight of the liquid composition, and an AZ-compound in an amount of at least 10 wt% and at most 30 wt%, preferably at least 15 wt% and at most 25 wt%, based on the total weight of the liquid composition.

[0134] A22 A liquid composition according to any one of A19 to A21 or any combination of the disclosures in subsections 1 and 3 and the entire specification, wherein the liquid composition comprises water in an amount of at least 50 wt% and at most 75 wt%, preferably at least 55 wt% and at most 70 wt%, based on the total weight of the liquid composition, and an AZ-compound in an amount of at least 25 wt% and at most 50 wt%, preferably at least 30 wt% and at most 45 wt%, based on the total weight of the liquid composition.

[0135] A23 A liquid composition according to any one of A19 to A22 or any combination of the disclosures in subsections 1 and 3 and the entire specification, wherein the liquid composition comprises water in an amount of at least 40 wt% and at most 70 wt%, preferably at least 45 wt% and at most 65 wt%, based on the total weight of the liquid composition, and an AZ-compound in an amount of at least 30 wt% and at most 60 wt%, preferably at least 35 wt% and at most 55 wt%, based on the total weight of the liquid composition.

[0136] A24 A liquid composition according to any one of A19 to A23 or any combination of the disclosures derived from subsections 1 and 3 and the entire specification, wherein the water is present in an amount of at least 30 wt% and at most 95 wt%, preferably at least 40 wt% and at most 85 wt%, more preferably at least 45 wt% and at most 85 wt%, for example at least 50 wt% and at most 70 wt%, for example at least 55 wt% and at most 65 wt%, based on the total weight of the liquid composition, and wherein the total amount of all components constituting the liquid composition mixture totals 100 wt%.

[0137] A25 A liquid composition according to any one of A19 to A24 or any combination of the disclosures derived from subsections 1 and 3 and the entire specification, wherein the liquid composition further comprises an organic solvent in an amount of at most 40 wt %, preferably at most 30 wt %, such as at most 25 wt %, such as at most 20 wt %, such as at most 12 wt %, such as at most 10 wt %, such as at most 8 wt %, such as at most 5 wt %, such as at most 4 wt %, such as 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 0.2 wt %, such as at most 0.1 wt %, based on the total weight of the liquid composition.

[0138] A26 A liquid composition according to any one of A19 to A25 or any combination of the disclosures from subsections 1 and 3 and the entire specification, wherein the liquid composition does not contain an organic solvent.

[0139] A27 A liquid composition according to any one of A19 to A26 or any combination of the disclosure arising from subsections 1 and 3 and the entire specification, wherein the composition has a pH value, determined according to ISO 976:2013 and according to the specification, 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 10 and at most 13, for example at least 10.5 and at most 12.0, for example at least 10.5 and at most 11.6, for example at least 10.5 and at most 11.5, provided that the liquid composition comprises water in an amount of at least 20% by weight, preferably at least 25% by weight, more preferably at least 30% by weight, most preferably at least 35% by weight, based on the total weight of the liquid composition.

[0140] A28 A liquid composition according to any one of A19 to A27 or any combination of the disclosures derived from subsections 1 and 3 and the entire specification, wherein the liquid composition 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) a mixture thereof, the amount of component T as determined by LC-MS according to the specification being at most 5 wt%, preferably at most 4 wt%, more preferably at most 3 wt%, for example at most 2 wt%, for example at most 1 wt%, for example at most 0.5 wt%, for example at most 0.1 wt%, for example at most 0.05 wt%, based on the total weight of the AZ compound.

[0141] A29 A liquid composition according to any one of A19 to 28 or any combination of the disclosures from subsections 1 and 3 and the entire specification, wherein the liquid composition does not contain component T.

[0142] A30 A liquid composition according to any one of A19 to A29 or any combination of the disclosures derived from subsections 1 and 3 and the entire specification, wherein the amount of chloride determined according to ASTM D1726-11 (2019) is at most 0.3 weight%, preferably at most 0.2 weight%, more preferably at most 0.1 weight%, for example at most 0.05 weight%, for example at most 0.03 weight%, based on the total weight of the liquid composition.

[0143] A31 A liquid composition according to any one of A19 to A30 or any combination of the disclosures from subsections 1 and 3 and the entire specification, wherein the liquid composition further comprises

[0144] iii) a polymer having an acid value in the range 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.

[0145] A32 A liquid composition according to any one of A19 to A31 or any combination of the disclosures derived from subsections 1 and 3 and the entire specification, wherein 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.

[0146] A33 A liquid composition according to any one of A19 to A32 or any combination of the disclosures derived from subsections 1 and 3 and the entire specification, wherein the polymer is present in an amount of at least 5 wt% and at most 65 wt%, preferably at least 10 wt% and at most 60 wt%, more preferably at least 20 wt% and at most 55 wt%, for example at least 30 wt% and at most 50 wt%, based on the total weight of the aqueous composition, and wherein the total amount of all components constituting the mixture totals 100 wt%.

[0147] A34 A liquid composition according to any one of A19 to A33 or any combination of the disclosures derived from subsections 1 and 3 and the entire specification, wherein the liquid composition is a coating composition, preferably a liquid coating composition.

[0148] A35 A kit of parts according to any combination of the disclosure from subsections 4, 3 and 1 and the entire specification, the kit of parts comprising parts A and B that are physically separate from each other, wherein:

[0149] i) part A comprises a liquid composition according to any one of A19 to A34 or any combination of the disclosure from subsections 1 and 3 and the entire specification; and

[0150] ii) part B comprises a polymer having an acid value in the range of 5 to 300 mg KOH / g, preferably 8 to 200 mg KOH / g, more preferably 10 to 150 mg KOH / g, determined according to ASTM D1639-90 (1996) e1, and wherein the polymer may optionally comprise ionic functional groups, and wherein the polymer is preferably selected from the group consisting of polyesters, polyamides, polycarbonates, polyimides, alkyds, urethane-modified alkyds (uralkyds), polyacrylics, polyurethanes, poly(urethane-acrylics) and mixtures thereof, more 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,

[0151] Part A does not contain the polymer of Part B, and Part B does not contain the liquid composition of Part A.

[0152] A36 A cured form of an AZ-component according to A1a or any one of A1 to A18 or any combination of the disclosures from subsections 4, 3 and 1 and the entire specification.

[0153] A37 A cured form according to A36, wherein the cured form is a film.

[0154] A38 A product comprising: i) an AZ-component according to any one of A1a and A1 to A13 or any combination of the disclosures in subsections 4, 3 and 1 and the entire specification; and / or ii) a liquid composition according to any one of A19 to A34 or any combination of the disclosures in subsections 4, 3 and 1 and the entire specification; and / or iii) a solidified form according to any one of A36 to A37 or any combination of the disclosures in subsections 4, 3 and 1 and the entire specification.

[0155] A39 An article according to A38 or any combination of the disclosures from Subsection 4, Subsection 3, and Subsection 1 and the entire specification, wherein the article is selected from the group consisting of textiles, glass, metal, composites, plastics, wood, engineered wood, imitation wood, leather, artificial leather, paper, fibers.

[0156] A40 Use of an AZ-component according to A1a or according to any one of A1 to A18 or any combination of the disclosure in subsection 1 and the entire specification, or a liquid composition according to any one of A19 to A34 or any combination of the disclosure in subsections 1 and 3 and the entire specification as a crosslinker.

[0157] A41 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, or medical devices:

[0158] i) an AZ-component according to any one of A1a and A1 to A18 or from any combination of the disclosure in subsections 4, 3 and 1 and the entire specification;

[0159] ii) a liquid composition according to any one of A19 to A34 or any combination of the disclosures from subsections 4, 3 and 1 and the entire specification;

[0160] iii) a kit of parts according to A35 or any combination of the disclosure from subsections 4, 3 and 1 and the entire specification;

[0161] iv) a solidified form according to any one of A36 to A37 or any combination of the disclosure from subsections 4, 3 and 1 and the entire specification;

[0162] v) An article according to any one of A38 to A39 or any combination of the disclosures from subsections 4, 3 and 1 and the entire specification.

[0163] All combinations of minimum and maximum values for parameters disclosed in this specification can be used to define parameter ranges for various preferences or embodiments of the present invention.

[0164] Unless expressly stated otherwise, any features, elements, components, embodiments, aspects, ranges and in particular any preferred features, preferred elements, preferred embodiments, preferred aspects, preferred ranges and preferred combinations of ranges, preferences, embodiments and aspects disclosed in A1a or any of A1 to A41 shown above in relation to any disclosure may be combined with each other and with any other features, elements, components, embodiments, aspects, ranges and in particular any preferred features, preferred elements, preferred embodiments, preferred aspects, preferred ranges and preferred combinations of ranges, preferences, embodiments and aspects of the invention disclosed throughout this specification.

[0165] Unless expressly stated otherwise, any features, elements, components, embodiments, aspects, ranges and in particular any preferred features, preferred elements, preferred embodiments, preferred aspects, preferred ranges and preferred combinations of ranges, preferences, embodiments and aspects of the present invention disclosed throughout this specification may be combined with each other.

[0166] definition

[0167] 'Aziridine ring' in the specification means a 3-membered ring system consisting of one nitrogen atom and two carbon atoms.

[0168] The term 'saturated hydrocarbylene' means a divalent organic group formed by removing two hydrogen atoms from a saturated hydrocarbon, the free valencies of which are not involved in a double bond. Exemplary hydrocarbylene groups include, but are not limited to, methylene.

[0169] The term 'saturated' means that the relevant entity does not contain any unsaturated groups.

[0170] The term 'ionic functional group' herein means a functional group comprising one or both of a cation and an anion, and the functional group is covalently bonded to an entity with which it is associated.

[0171] 'Poor chemical resistance' with respect to a cured coating (film) means in this specification that the chemical resistance of the film measured as described in the specification is at most 1 [on a scale of 0 to 5, where 5 represents the best performance and 0 represents the worst performance, the scale being as disclosed in the specification].

[0172] 'Reasonable chemical resistance' with respect to a cured coating (film) means in this specification that the film has a chemical resistance of 2 [on a scale of 0 to 5, where 5 represents the best performance and 0 represents the worst performance, the scale being as disclosed in the specification], measured as described in the specification.

[0173] 'Good chemical resistance' with respect to the cured coating (film) means in this specification that the chemical resistance of the film measured as described in the specification is 3 [on a scale of 0 to 5, where 5 represents the best performance and 0 represents the worst performance, the scale being as disclosed in the specification].

[0174] 'Very good chemical resistance' with respect to the cured coating (film) means in this specification that the chemical resistance of the film measured as described in the specification is 4 [on a scale of 0 to 5, where 5 represents the best performance and 0 represents the worst performance, the scale being as disclosed in the specification].

[0175] 'Excellent chemical resistance' with respect to a cured coating (film) means in this specification that the chemical resistance of the film measured as described in the specification is 5 [on a scale of 0 to 5, where 5 represents the best performance and 0 represents the worst performance, the scale being as disclosed in the specification].

[0176] 'Poor cross-linking efficiency' with respect to an entity is meant in this specification to mean that the entity has poor end chemical resistance, or equivalently, that the end chemical resistance of the entity is poor.

[0177] By 'reasonable cross-linking efficiency' of an entity is meant in this specification that the entity has a reasonable end chemical resistance, or equivalently, that the end chemical resistance of the entity is reasonable.

[0178] 'Good cross-linking efficiency' with respect to an entity means in this specification that the entity has good end chemical resistance, or equivalently, that the end chemical resistance of the entity is good.

[0179] 'Very good cross-linking efficiency' with respect to an entity means in the present specification that the entity has very good end chemical resistance, or equivalently, that the end chemical resistance of the entity is very good.

[0180] 'Excellent cross-linking efficiency' with respect to an entity means in this specification that the entity has excellent end chemical resistance, or equivalently, that the end chemical resistance of the entity is excellent.

[0181] In the context of this specification, genotoxicity is defined as the Assay (Toxys, Leiden, the Netherlands). In the context of this specification, "positive induction of genotoxicity" means that the induction level of the biomarkers Bscl2-GFP and Rtkn-GFP in the absence or presence of a metabolic system rat S9 liver extract is equal to or higher than 2-fold at at least one of 10%, 25% and 50% cytotoxicity. In the context of this specification, "weak positive induction of genotoxicity" means that the induction level of the biomarkers Bscl2-GFP and Rtkn-GFP in the absence or presence of a metabolic system based on rat S9 liver extract (aroclor1254-induced rat, Moltox, Boone, NC, USA) is higher than 1.5-fold and lower than 2-fold at at least one of 10%, 25% and 50% cytotoxicity (but lower than 2-fold at 10%, 25% and 50% cytotoxicity). In the context of this specification, "genotoxicity comparable to naturally occurring background" means that the induction levels of the biomarkers Bscl2-GFP and Rtkn-GFP in the absence and presence of a metabolic system based on rat S9 liver extract (aroclor1254-induced rats, Boone, NC, USA) are less than or equal to 1.5-fold at 10%, 25%, and 50% cytotoxicity. In the absence and presence of a metabolic system based on rat S9 liver extract (aroclor1254-induced rats, Moltox, Boone, NC, USA), the induction levels of the genotoxicity reporter genes Bscl2-GFP and Rtkn-GFP are preferably less than or equal to 1.5-fold at 10%, 25%, and 50% cytotoxicity. In the context of this specification, "non-genotoxic" (or equivalently "not genotoxic") means that the induction level shown in the absence and presence of a rat S9 liver extract-based metabolic system (aroclor1254-induced rat, Moltox, Boone, NC, USA) at 10%, 25% and 50% cytotoxicity is less than 2 times, preferably equal to or less than 1.9 times, more preferably equal to or less than 1.8 times, for example equal to or less than 1.7 times, for example equal to or less than 1.6 times, for example equal to or less than 1.5 times.

[0182] 'Room temperature' herein means 23±1°C.

[0183] 'Atmospheric pressure' in this specification means a pressure of 1 atm.

[0184] 'Standard conditions' in this specification generally refers to room temperature and atmospheric pressure.

[0185] 'Below' in this specification means that the relevant maximum limit value is not included in the range.

[0186] 'Above' in this specification means that the relevant minimum boundary value is not included in the range.

[0187] 'rpm' means revolutions per minute.

[0188] 'Polyacrylic' in this specification means any polymer comprising the 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' in this specification means any polymer consisting 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. any polymer consisting of the reaction residues of acrylic acid and / or methacrylic acid and / or acrylic acid esters and / or methacrylic acid esters and / or styrene, and / or acrylonitrile, and / or acrylamide, and / or itaconic acid esters, and / or itaconic acid, and / or divinylbenzene, and / or methacrylonitrile, and / or vinyl esters and / or vinyl halides, and / or fumarate esters and / or fumaric acid; preferably, "vinyl polymer" in this specification refers to any polymer consisting of the reaction residues of acrylic acid and / or methacrylic acid and / or acrylic acid esters and / or methacrylic acid esters and / or styrene, and / or acrylonitrile, and / or acrylamide, and / or itaconic acid esters, and / or itaconic acid, and / or divinylbenzene, and / or methacrylonitrile, and / or vinyl esters and / or vinyl halides, and / or fumarate esters, and / or fumaric acid.

[0189] 'Epoxy protons' in this specification means the two protons of the methylene group (-CH2-) of an oxirane (also known as epoxy) group having the formula

[0190]

[0191] 'Curing' as used herein means the process of becoming 'fixed' to form an irreversible cross-linked network (so-called 'cured form' or 'cured composition') in which the material no longer flows, melts or dissolves. The terms 'curing' and 'cross-linking' are used interchangeably herein. Curing can be carried out under standard conditions (as defined in this specification), or by applying heat, or by applying pressure, or by applying a vacuum, or by radiation, such as ultraviolet radiation, or by any combination thereof.

[0192] Characterization of the physical state of a chemical entity, such as a composition, is evaluated under and with reference to standard conditions. For example, if a composition is characterized as a "liquid composition," it means that the composition is liquid at room temperature and atmospheric pressure.

[0193] 1. (Aziridine hydroxy)-functional organic components (AZ-components) of the present invention

[0194] The (aziridinylhydroxy)-functional organic components (AZ-components) of the present invention are disclosed throughout this specification. As used in this specification, the term 'AZ-component' includes any and all combinations of preferences, features, and ranges thereof, as well as any and all combinations of preferences with any and all combinations of features and ranges thereof. Thus, any and all references to AZ components disclosed in subsection 1 and its subsections include any and all preferences, combinations of features, and ranges thereof, as well as any and all preferences with any and all features and ranges thereof—collectively, throughout this specification—are referred to as AZ components.

[0195] The AZ-component is according to any one of A1a or A1 to A18 or any combination disclosed throughout the specification. More specifically, 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 (AZ5 compound) of formula A5 having only six aziridine rings; and vi) a mixture thereof, preferably, the AZ component is selected from the group consisting of the following i) to iv): i) an (aziridinylhydroxy)-functional organic compound AZ1 (AZ1 compound) of formula A1 having only two aziridine rings; ii) an (aziridinylhydroxy)-functional organic compound AZ2 (AZ2 compound) of formula A2 having only three aziridine rings; iii) an (aziridinylhydroxy)-functional organic compound AZ3 (AZ3 compound) of formula A3 having only four aziridine rings; and iv) a mixture thereof,

[0196]

[0197] in

[0198] X1 is a divalent aliphatic organic group or a divalent aromatic organic group, preferably X1 is a divalent aliphatic organic group;

[0199] X2 is a trivalent aliphatic organic group or a trivalent aromatic organic group, preferably X2 is a trivalent aliphatic organic group;

[0200] X3 is a tetravalent aliphatic organic group or a tetravalent aromatic organic group, preferably X3 is a tetravalent aliphatic organic group;

[0201] X4 is a pentavalent aliphatic organic group or a pentavalent aromatic organic group, preferably X4 is a pentavalent aliphatic organic group;

[0202] X5 is a hexavalent aliphatic organic group or a hexavalent aromatic organic group, preferably X5 is a hexavalent aliphatic organic group;

[0203] and wherein each of said X1 to X5 consists of a collection of covalently linked atoms in a configuration comprising linear and / or branched and / or cyclic structures, preferably consisting of linear and / or branched and / or cyclic structures, said collection 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 viiii),

[0204] and wherein each of said X1 to X5 has a carbon atom and a hydrogen atom,

[0205] and wherein each of said X1 to X5 optionally has an oxygen atom and / or a nitrogen atom and / or a sulfur atom and / or a silicon atom,

[0206] and wherein X1 and / or X2 and / or X3 and / or X4 and / or X5 may optionally contain an ionic functional group, preferably X1 and / or X2 and / or X3 and / or X4 and / or X5 do not contain an ionic functional group,

[0207] And among them

[0208] 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,

[0209]

[0210]

[0211] And among them

[0212] R1 is selected from the group consisting of: hydrogen and methyl; and

[0213] R2 is selected from the group consisting of hydrogen, methyl and C2-C5 alkyl; and

[0214] R3 is selected from the group consisting of: methyl and C2-C4 alkyl; and

[0215] R4 is selected from the group consisting of hydrogen, methyl and C2-C4 alkyl;

[0216] And among them

[0217] 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 the Y and each of the X1 to X5 is selected from the group consisting of a carbon-carbon single bond, a carbon-oxygen single bond and a carbon-nitrogen single bond, preferably a carbon-oxygen single bond and a carbon-nitrogen single bond, more preferably a carbon-oxygen single bond,

[0218] And among them

[0219] Each of compounds AZ1 to AZ5 has a molecular weight of at least 600 Da and at most 10000 Da, preferably at least 600 Da and at most 8000 Da, more preferably at least 600 Da and at most 7000 Da, even more preferably at least 600 Da and at most 6000 Da, for example at least 600 Da and at most 5500 Da, for example at least 600 Da and at most 5000 Da, for example at least 600 Da and at most 4000 Da, for example at least 600 Da and at most 3500 Da, for example at least 600 Da and at most 3200 Da, for example at least 600 Da and at most 3000 Da, for example at least 600 Da and at most 2500 Da, for example at least 600 Da and at most 2200 Da, for example At least 600 Da and at most 2000 Da, for example at least 630 Da and at most 10000 Da, for example at least 630 Da and at most 8000 Da, for example at least 630 Da and at most 7000 Da, for example at least 630 Da and at most 6000 Da, for example at least 630 Da and at most 5500 Da, for example at least 630 Da and at most 5000 Da, for example at least 630 Da and at most 4000 Da, for example at least 630 Da and at most 3500 Da, for example at least 630 Da and at most 3200 Da, for example at least 630 Da and at most 3000 Da, for example at least 630 Da and at most 2500 Da, for example at least 630 Da and at most 22 00 Da, for example at least 630 Da and at most 2000 Da, for example at least 640 Da and at most 10000 Da, for example at least 640 Da and at most 8000 Da, for example at least 640 Da and at most 7000 Da, for example at least 640 Da and at most 6000 Da, for example at least 640 Da and at most 5500 Da, for example at least 640 Da and at most 5000 Da, for example at least 640 Da and at most 4000 Da, for example at least 640 Da and at most 3500 Da, for example at least 640 Da and at most 3200 Da, for example at least 640 Da and at most 3000 Da, for example at least 640 Da and at most 2500 Da, for example at least 640 Da and at most 2200 Da, for example at least 640 Da and at most 2000 Da, for example at least 650 Da and at most 10000 Da, for example at least 650 Da and at most 8000 Da, for example at least 650 Da and at most 7000 Da, for example at least 650 Da and at most 6000 Da, for example at least 650 Da and at most 5500 Da, for example at least 650 Da and at most 5000 Da, for example at least 650 Da and at most 4000 Da, for example at least 650 Da and at most 3500 Da, for example at least 650 Da and at most 3200 Da, for example at least 650 Da and at most 3000 Da, for example at least 650 Da and at most 2500 Da,For example at least 650 Da and at most 2200 Da, for example at least 650 Da and at most 2000 Da, for example at least 700 Da and at most 10000 Da, for example at least 700 Da and at most 8000 Da, for example at least 700 Da and at most 7000 Da, for example at least 700 Da and at most 6000 Da, for example at least 700 Da and at most 5500 Da, for example at least 700 Da and at most 5000 Da, for example at least 700 Da and at most 4000 Da, for example at least 700 Da and at most 3500 Da, for example at least 700 Da and at most 3200 Da, for example at least 700 Da and at most 3000 Da, for example at least 700 Da and at most 2500 Da, For example at least 700 Da and at most 2200 Da, for example at least 700 Da and at most 2000 Da, for example at least 750 Da and at most 10000 Da, for example at least 750 Da and at most 8000 Da, for example at least 750 Da and at most 7000 Da, for example at least 750 Da and at most 6000 Da, for example at least 750 Da and at most 5500 Da, for example at least 750 Da and at most 5000 Da, for example at least 750 Da and at most 4000 Da, for example at least 750 Da and at most 3500 Da, for example at least 750 Da and at most 3200 Da, for example at least 750 Da and at most 3000 Da, for example at least 750 Da and at most 2500 Da, For example at least 750 Da and at most 2200 Da, for example at least 750 Da and at most 2000 Da, for example at least 800 Da and at most 10000 Da, for example at least 800 Da and at most 8000 Da, for example at least 800 Da and at most 7000 Da, for example at least 800 Da and at most 6000 Da, for example at least 800 Da and at most 5500 Da, for example at least 800 Da and at most 5000 Da, for example at least 800 Da and at most 4000 Da, for example at least 800 Da and at most 3500 Da, for example at least 800 Da and at most 3200 Da, for example at least 800 Da and at most 3000 Da, for example at least 800 Da and at most 2500 Da, For example, at least 800 Da and at most 2200 Da, for example, at least 800 Da and at most 2000 Da, for example, at least 850 Da and at most 10000 Da, for example, at least 850 Da and at most 8000 Da, for example, at least 850 Da and at most 7000 Da, for example, at least 850 Da and at most 6000 Da, for example, at least 850 Da and at most 5500 Da, for example, at least 850 Da and at most 5000 Da, for example, at least 850 Da and at most 4000 Da, for example, at least 850 Da and at most 3500 Da, for example, at least 850 Da and at most 3200 Da, for example, at least 850 Da and at most 3000 Da, for 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 Such as 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 1500 Da 1000Da and at most 2500Da, for example at least 1000Da and at most 2200Da, for example at least 1000Da and at most 2000Da, for example at least 1100Da and at most 10000Da, for example at least 1100Da and at most 8000Da, for example at least 1100Da and at most 7000Da, for example at least 1100Da and at most 6000Da, for example at least 1100Da and at most 5500Da, for example at least 1100Da and at most 5000Da, for example at least 1100Da and at most 4000Da, for example at least 1100Da and at most 3500Da, for example at least 1100Da and at most 3200Da, for example at least 1100Da and at most 3000Da,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. ,

[0220] Preferably, X1 is a divalent aliphatic organic group or a divalent aromatic organic group different from the divalent group of bisphenol A.

[0221] Preferably, the AZ-component disclosed in the specification, wherein X1 is a divalent aliphatic organic group or a divalent aromatic organic group different from a divalent organic group selected from the group consisting of: a divalent group of bisphenol A, a divalent group of bisphenol AP, a divalent group of bisphenol AF, a divalent group of bisphenol B, a divalent group of bisphenol BP, a divalent group of bisphenol C, a divalent group of bisphenol C2, a divalent group of bisphenol E, a divalent group of bisphenol F, a divalent group of bisphenol G, a divalent group of bisphenol M, a divalent group of bisphenol S, a divalent group of bisphenol P, a divalent group of bisphenol PH, a divalent group of bisphenol TMC, a divalent group of bisphenol Z, a divalent group of dinitrobisphenol A, a divalent group of tetrabromobisphenol A, and a combination thereof, preferably X1 is a divalent aliphatic organic group.

[0222] Preferably, the AZ-component disclosed in the specification, wherein X1 and / or X2 and / or X3 and / or X4 and / or 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, preferably comprises at least one structural unit or a 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:

[0223]

[0224] in

[0225] R' is selected from the group consisting of: hydrogen and methyl; and

[0226] j is an integer ranging from 1 to 5, preferably from 1 to 3; and

[0227] n is in the range of 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 (for example 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 (for example 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 (for example, 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 (for example, n is 5), for example, from and including 6 up to and including 50, for example, from and including 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 (for example, 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 (for example, 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 10 Integers including 20, for example, from and including 8 up to and including 15, for example, from and including 8 up to and including 10 (for example, 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 (for example, 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 (for example, n is 10).

[0228] Preferably, the AZ-component disclosed in the specification, wherein

[0229] R1 is selected from the group consisting of: hydrogen and methyl; and

[0230] R2 is selected from the group consisting of: hydrogen, methyl and ethyl; and

[0231] R3 is selected from the group consisting of: methyl and C2-C4 alkyl; and

[0232] R4 is selected from the group consisting of hydrogen, methyl and ethyl.

[0233] Preferably, the aggregate number of carbon atoms in R1, R2, R3 and R4 in the AZ-component disclosed in the specification is at most 9, preferably at most 4, more preferably at most 2, such as at most 1.

[0234] Preferably, the AZ-component disclosed in the specification, wherein the X1 and / or the X2 and / or the X3 and / or the X4 and / or the X5 do not contain one or any combination of the following structural units BP1, BP2, BP3 and BS

[0235]

[0236]

[0237] Preferably, the AZ-component disclosed in the specification, wherein X1 and / or X2 and / or X3 and / or X4 and / or X5 comprises at least one unit 11 as a structural unit.

[0238] Preferably, X1 is a divalent aliphatic organic group of formula A1a'

[0239]

[0240] in

[0241] R' is selected from the group consisting of: hydrogen and methyl; and

[0242] j is an integer ranging from 1 to 5, preferably from 1 to 3; and

[0243] n is in the range of 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 (for example 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 (for example 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 (for example, 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 (for example, n is 5), for example, from and including 6 up to and including 50, for example, from and including 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 (for example, 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 (for example, 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 10 Integers including 20, for example, from and including 8 up to and including 15, for example, from and including 8 up to and including 10 (for example, 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 (for example, 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 (for example, n is 10).

[0244] Preferably, the AZ-component disclosed in the specification, wherein each of X1 to X5 comprises only single covalent bonds, or both single covalent bonds and double covalent bonds, and wherein the single covalent bond is selected from the group consisting of a carbon-carbon single bond, a carbon-hydrogen single bond, a carbon-nitrogen single bond, a carbon-sulfur single bond, a carbon-silicon single bond, a silicon-oxygen single bond, a nitrogen-hydrogen single bond, a sulfur-oxygen single bond, a carbon-oxygen single bond in which oxygen is bonded to hydrogen to form a hydroxyl group, a silicon-oxygen-silicon single bond, and wherein the double covalent bond is selected from the group consisting of a carbon-carbon double bond, a carbon-nitrogen double bond, a sulfur-oxygen double bond, a carbon-oxygen double bond in which carbon is a member of a ring structure, and a carbon-carbon double bond in which carbon is bonded to two other carbon atoms via a carbon-carbon single bond. Preferably, the double covalent bond is selected from the group consisting of a carbon-carbon double bond, a carbon-nitrogen double bond, a sulfur-oxygen double bond, a carbon-oxygen double bond in which carbon is a member of a ring structure, and a carbon-oxygen double bond in which carbon is bonded to two other carbons through a carbon-carbon single bond, a carbon-oxygen double bond in which carbon is bonded to another oxygen and to nitrogen through a single bond, and a carbon-oxygen double bond in which carbon is bonded to two nitrogens through a carbon-nitrogen single bond.

[0245] Preferably, the aggregation 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%, such as at least 25%, such as at least 30%, such as at least 35%, such as at least 40%, such as at least 45%, such as at least 50%, such as at least 55%, such as at least 60%, such as at least 65%, such as at least 70%, such as at least 75%, such as at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 97%, such as at least 98%, such as at least 99%, such as 100%, relative to the aggregation number of all atoms present in X1 and / or X2 and / or X3 and / or X4 and / or X5, respectively.

[0246] Preferably, 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, such as at most 400, such as at most 350, such as at most 300, such as at most 250, such as at most 200.

[0247] Preferably, the AZ component is selected from the group consisting of: i) an (aziridinylhydroxy)-functional organic compound AZ1 of formula A1 (AZ1 compound), ii) an (aziridinylhydroxy)-functional organic compound AZ2 of formula A2 (AZ2 compound), iii) an (aziridinylhydroxy)-functional organic compound AZ3 of formula A3 (AZ3 compound), iv) an (aziridinylhydroxy)-functional organic compound AZ5 of formula A5 (AZ5 compound), and vi) a mixture thereof, and

[0248] in

[0249] 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 as follows

[0250]

[0251] 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, 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 is equal to 4); and

[0252]

[0253] Wherein R in formula A1b is C3-C 10 a 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, 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 is equal to 4);

[0254] and

[0255]

[0256] 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 is equal to 4),

[0257] and

[0258]

[0259] Wherein R in formula A1d is C3-C 10 saturated alkylene, 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, 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 is equal to 4),

[0260] and

[0261] in

[0262] 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 which is described below.

[0263]

[0264] wherein n in Formula A2a is an integer ranging from and including 2 up to and including 20, for example, from and including 2 up to and including 10, for example, from and including 2 up to and including 8, 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 8, for example, from and including 4 up to and including 20, for example, from and including 4 up to and including 10, for example, from and including 4 up to and including 8, for example, from and including 5 up to and including 20, for example, from and including 5 up to and including 10, for example, from and including 5 up to and including 8, for example, from and including 6 up to and including 20, for example, from and including 6 up to and including 10, for example, from and including 6 up to and including 8 (for example, n is equal to 7);

[0265] and

[0266]

[0267] wherein each n in formula A2b is independently selected, and each n in formula A2b ranges 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 an integer 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 (for example n is equal to 11);

[0268] and

[0269]

[0270] wherein each n in formula A2c is independently selected, and each n in formula A2c ranges 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 an integer 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 (for example n is equal to 11);

[0271] and

[0272]

[0273] and

[0274]

[0275] and

[0276] in

[0277] The AZ3 compound is selected from the group consisting of: a compound having formula A3a

[0278]

[0279] wherein 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 (for example n equals 3, for example n equals 2);

[0280] and

[0281] in

[0282] The AZ5 compound is selected from the group consisting of: a compound having formula A5a

[0283]

[0284] wherein 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 (for example n equals 4, for example n equals 3).

[0285] Preferably, X1 and / or X2 and / or X3 and / or X4 and / or X5 do not comprise any structural units of (or equivalently derived from) phenol-formaldehyde resins (also known as novolac resins); 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 resol resins (base-catalyzed PF resins with a formaldehyde to phenol ratio greater than 1, typically equal to 1.5).

[0286] Preferably, the AZ component is selected from the group consisting of: an AZ1 compound, and wherein the AZ1 compound is a compound of the formula,

[0287]

[0288] Preferably, the AZ component is selected from the group consisting of: an AZ2 compound, and wherein the AZ2 compound is a compound of the formula,

[0289]

[0290] Preferably, the AZ component is selected from the group consisting of: an AZ2 compound, and wherein the AZ2 compound is a compound of the formula,

[0291]

[0292] Preferably, the AZ component is selected from the group consisting of: an AZ2 compound, and wherein the AZ2 compound is a compound of the formula,

[0293]

[0294] Preferably, the AZ1 compound and / or the AZ2 compound and / or the AZ3 compound and / or the AZ4 compound and / or the AZ5 compound contain 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 said 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%, for example at least 30 mol% and at most 65 mol%, for example 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 to which these mol% relate.

[0295] Preferably, the AZ1 compound and / or the AZ2 compound and / or the AZ3 compound and / or the AZ4 compound and / or the AZ5 compound comprises a methoxypoly(ethylene glycol) (MPEG) and / or poly(ethylene glycol) (PEG) group (each of these groups having a calculated number average molecular weight (M) greater than 1600 Da, preferably 2200 Da). n)), preferably, the amount of said 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%, for example at least 7 mol% and at most 20 mol%, for example at least 8 mol% and at most 17 mol%, for example at least 9 mol% and at most 15 mol%, for example 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 to which these mol% relate.

[0296] Preferably, the AZ1-compound and / or the AZ2-compound and / or the AZ3-compound and / or the AZ4-compound and / or the AZ5-compound contain groups with sulfonate functionality, which can be obtained, for example, by reacting epoxy groups with amino-functional sulfonic acid groups, such as 2-(cyclohexylamino)ethanesulfonic acid and 3-(cyclohexylamino)propanesulfonic acid. These sulfonate-functional groups are preferably neutralized with a base, more preferably with an inorganic base. For example, the reaction between the epoxy groups and the groups having sulfonate functionality can be carried out by reacting some of the epoxy groups of the polyepoxide with aziridine-AZIR before the reaction - this is defined in the specification; see Section 2, or by reacting with aziridine-AZIR during the reaction or by stopping the reaction between the polyepoxide and aziridine-AZIR at a certain point, for example by distilling off the excess aziridine-AZIR and then reacting some or all of the remaining epoxy groups with amino-functional sulfonic acid molecules [2-(cyclohexylamino)ethanesulfonic acid and 3-cyclohexyl-amino)propanesulfonic acid]. Alternatively, taurates can also be used, preferably taurine neutralized with sodium hydroxide, potassium hydroxide or lithium hydroxide.

[0297] Preferably, the AZ-component is 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.

[0298] 2. Method for producing AZ components

[0299] In principle, the (aziridinylhydroxy)-functional organic component (AZ component) as described in this specification is preferably obtained by reacting an aziridine of the formula AZIR (abbreviated 'aziridine-AZIR') with at least one polyepoxide having at least two and at most six epoxy groups.

[0300]

[0301] in

[0302] R1 is selected from the group consisting of: hydrogen and methyl; and

[0303] R2 is selected from the group consisting of hydrogen, methyl and C2-C5 alkyl; and

[0304] R3 is selected from the group consisting of: methyl and C2-C4 alkyl; and

[0305] R4 is selected from the group consisting of hydrogen, methyl and C2-C4 alkyl.

[0306] Exemplary aziridines of formula AZIR include, but are not limited to, propylene imine, 1,2-dimethylaziridine, 2,2-dimethylaziridine, 2-ethylaziridine, butylaziridine.

[0307] More specifically, the AZ1 compound (as described herein) is 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, such as commercially available from CVC Thermoset Specialties. GE-24.

[0308] More specifically, the AZ2 compound (as described herein) is 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 AZIR, all of which are commercially available from CVC Thermoset Specialties. GE-36 and 9000.

[0309] More specifically, the AZ3 compound (as described herein) is 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, such as polyol R4410 available from Perstop.

[0310] More specifically, AZ4 compounds (as described herein) are 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.

[0311] More specifically, the AZ5 compound (as described herein) 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.

[0312] The reaction (which term refers to and encompasses any and all reactions mentioned immediately 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 achieved by 1 The reaction proceeds as long as the epoxy groups react; this is done by 1 The characteristic properties of the epoxy protons were monitored and verified by H-NMR spectroscopy. 1 The H-NMR chemical shift (2.5-3ppm) disappears. Preferably, the reaction is carried out in the absence of a solvent. However, if necessary (e.g., to reduce viscosity), one or more solvents, such as methanol, ethanol, toluene, may be used during or after the reaction. If a solvent is used, it is generally convenient to first dissolve the polyepoxide in a solvent (or solvent mixture) before adding the aziridine-AZIR to the reaction mixture. The molar ratio of the number of moles of the aziridine groups of the 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 at 70° C. under reduced pressure of 20 to 50 mbar, more preferably at 70° C. under reduced pressure of 30 to 45 mbar. Subsequently, a further distillation step is carried out at 25 to 40° C. under 2 to 4 mbar to remove any unreacted aziridine-AZIR and any other volatiles until the reaction is complete. 1H-NMR spectroscopy does not detect aziridine-AZIR. It is generally useful to add additional solvent to the reaction mixture before or during distillation to help remove excess aziridine-AZIR. If necessary, a base can be used during the reaction to reduce possible acid sources. The base includes both an organic base (such as a tertiary amine) or an inorganic base (such as sodium carbonate or potassium carbonate or, for example, calcium hydroxide). The inorganic base can be filtered off after the reaction is complete.

[0313] For example, the compound AZ2 of formula A2d

[0314]

[0315] You can use It was prepared by reacting 9000 (6.26 mmol) (available from CVC Thermoset Specialties) with propylene imine (70.22 mmol) in the presence of potassium carbonate (250 mg) at 80°C for 3 h.

[0316]

[0317] A high excess of propylene imine is usually used to dissolve 9000 (the ratio of the number of moles of aziridine-AZIR to the number of moles of epoxy groups. The reaction can be carried out by 1 H-NMR monitoring. After 3 h at 80 ° C, the chemical shift of the epoxidation proton was 1 It is not visible in H-NMR; only some small peaks due to impurities. Once the reaction mixture is kept at 80 ° C for 3h to 22h, 1 The H-NMR spectrum was unchanged. The reaction mixture was cooled to room temperature and diluted with toluene. The potassium carbonate was filtered off, and the excess propyleneimine was distilled off with toluene at 70°C and 40 mbar. The residue was held at 90-95°C and a reduced pressure of 3-4 mbar (oil pump) for 2 hours to remove any residual propyleneimine and toluene. The reaction product solidified rapidly upon cooling. 1 H-NMR did not show any peaks attributable to any residual propylene imine.

[0318] In principle, in the process for producing an AZ compound wherein Y is a monovalent (aziridinylhydroxycyclohexane) organic group of formula B2 or a monovalent (aziridinylhydroxycyclohexane) organic group of formula B3, the AZ compound is preferably obtained by reacting cyclohexene hydroxyoxide with an isocyanurate of a diisocyanate and then with an aziridine-AZIR (e.g., propyleneimine). For example, the AZ component wherein Y is a monovalent (aziridinylhydroxycyclohexane) organic group of formula B2 or a monovalent (aziridinylhydroxycyclohexane) organic group of formula B3 can be prepared from 1-cyclohexene hydroxyoxide (see the following formula):

[0319]

[0320] The 1-hydroxycyclohexene oxide is obtained by epoxidation of 1-hydroxycyclohexene with peracetic acid. The 1-hydroxycyclohexene oxide is reacted with the isocyanurate of hexamethylene diisocyanate, followed by a 3-fold excess of propylene imine at 80°C for 24 hours. The excess propylene imine is then distilled off under reduced pressure at 50°C. The resulting AZ compound has a molecular weight of 1018 Da.

[0321] Alternatively, a polyoxyalkylene group containing at least one amino group (preferably a secondary amino group) or at least one carboxylic acid 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 that can introduce a polyether group into any of X1 to X5.

[0322] Alternatively, the aziridine-AZIR can be partially reacted with a polyoxyalkylene containing at least one carboxylic acid functional group and then reacted with the polyepoxide, as described above. This can be a reaction scheme that can introduce a polyether group into any of X1 to X5.

[0323] Preferably, the monohydroxy or monoamine functional polyether may be reacted with 2,4-toluene diisocyanate in a 1:1 molar ratio, and its reaction may subsequently react with some of the hydroxyl groups formed after the reaction of the imine with the epoxy compound.

[0324] 3. Liquid composition of the present invention

[0325] The liquid compositions of the present invention are as disclosed throughout this specification. As used in this specification, the term 'liquid composition of the present invention' (or alternatively, 'liquid composition of the present invention') includes any and all combinations of preferences, features, and ranges thereof, as well as any and all combinations of preferences and features and ranges thereof. Thus, any and all liquid compositions of the present invention disclosed in this subsection 3, including any and all combinations of preferences, features, and ranges thereof, as well as any and all combinations of preferences and features and ranges thereof, are collectively referred to throughout this specification as liquid compositions of the present invention.

[0326] The liquid composition of the present invention is according to any one of A19 to A34 and as disclosed throughout the specification. More specifically, the liquid composition of the present invention comprises at 23±1°C and atmospheric pressure:

[0327] i) a liquid medium selected from organic solvents, water and mixtures thereof in an amount of at most 90 wt %, preferably at most 85 wt %, more preferably at most 80 wt %, such as at most 75 wt %, for example at most 70 wt %, for example at most 65 wt %, for example at most 60 wt %, for example at most 55 wt %, for example at most 50 wt %, for example at most 45 wt %, for example at most 40 wt %, for example at most 35 wt %, for example at most 30 wt %, for example at most 25 wt %, for example at most 20 wt %, for example at most 15 wt %, for example at most 10 wt %, for example at most 5 wt %, for example at most 2 wt %, for example at most 1 wt %, for example the liquid composition contains no liquid medium; and

[0328] ii) the AZ-components disclosed in the specification; and

[0329] The total amount of all components constituting the liquid composition adds up to 100% by weight.

[0330] The liquid composition of the present invention can be prepared by mixing a liquid medium - as disclosed throughout the specification - with AZ-components - as disclosed throughout the specification. The mixing of the liquid medium and AZ-components can be carried out under standard conditions.

[0331] The liquid compositions of the present invention can be solutions in organic solvents, solutions in water, or aqueous dispersions (with or without organic solvents). Dissolving the AZ components in the organic solvent can be accomplished by gentle stirring and, if desired, by gentle heating, e.g., up to 40°C, to facilitate and accelerate dissolution. If desired, mixtures of organic solvents or mixtures of water and organic solvents can be used. If desired, other components can be mixed with the AZ component solution, including, for example, a plasticizer, a base (preferred bases for neutralization are inorganic bases such as sodium, potassium, or lithium hydroxides, secondary and tertiary amines), and a dispersant. If desired, the AZ components can be dispersed in water by any technique, preferably using one or more bases such as tertiary amines or inorganic bases such as sodium hydroxide, by using the AZ components themselves, or by first dissolving the AZ components in a preferably water-miscible solvent and adding a dispersant, preferably a nonionic dispersant; even more preferably, the dispersant is polymeric in nature and contains ionic functional groups, such as polyethylene oxide groups and / or sulfonate groups. Water is added to the above mixture with stirring, and the mixture can be diluted with additional water, if necessary, to achieve the target solids content of the final dispersion. If desired, the solvent can be removed after the aqueous dispersion is obtained.

[0332] Preferably, the liquid composition of the present invention is an aqueous dispersion comprising water in an amount of at least 20% by weight and at most 55% by weight, based on the total weight of the liquid composition (in this case the total weight of the aqueous dispersion), and wherein the aqueous dispersion has a pH, measured according to ISO 976:2013 and according to the specification, 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 10 and at most 13, for example at least 10.5 and at most 12.0, for example at least 10.5 and at most 11.6, for example at least 10.5 and at most 11.5. Dispersions in water facilitate metering of aqueous polymer systems and can reduce VOC levels because less or no organic solvent is needed to obtain a controllable metering viscosity. The dispersion can optionally be prepared with the aid of an organic solvent which can be removed after dispersing the components in water. Typically, the organic solvent is removed by distillation.

[0333] Preferably, the liquid composition according to the present invention comprises water in an amount of at most 90 wt.-%, preferably at most 85 wt.-%, more preferably at most 80 wt.-%, most preferably at most 75 wt.-%, such as at most 70 wt.-%, such as at most 65 wt.-%, for example at most 60 wt.-%, such as at most 55 wt.-%, for example at most 50 wt.-%, such as at most 45 wt.-%, for example at most 40 wt.-%, such as at most 35 wt.-%, for example at most 30 wt.-%, for example at most 25 wt.-%, for example at most 20 wt.-%, such as at most 15 wt.-%, for example at most 10 wt.-%, for example at most 5 wt.-%, for example at most 2 wt.-%, for example at most 1 wt.-%, e.g. the liquid composition according to the present invention contains no water.

[0334] Preferably, the liquid composition according to the present invention comprises at least 70 wt.-% and at most 90 wt.-%, preferably at least 75 wt.-% and at most 85 wt.-% of water, based on the total weight of the liquid composition according to the present invention, and at least 10 wt.-% and at most 30 wt.-%, preferably at least 15 wt.-% and at most 25 wt.-% of an AZ-compound, based on the total weight of the liquid composition according to the present invention.

[0335] Preferably, the liquid composition according to the present invention comprises at least 50 wt.-% and at most 75 wt.-%, preferably at least 55 wt.-% and at most 70 wt.-% of water, based on the total weight of the liquid composition according to the present invention, and at least 25 wt.-% and at most 50 wt.-%, preferably at least 30 wt.-% and at most 45 wt.-% of an AZ-compound, based on the total weight of the liquid composition according to the present invention.

[0336] Preferably, the liquid composition according to the present invention comprises at least 40 wt.-% and at most 70 wt.-%, preferably at least 45 wt.-% and at most 65 wt.-% of water, based on the total weight of the liquid composition according to the present invention, and at least 30 wt.-% and at most 60 wt.-%, preferably at least 35 wt.-% and at most 55 wt.-% of an AZ-compound, based on the total weight of the liquid composition according to the present invention.

[0337] Preferably, water is present in the liquid composition according to the present invention in an amount of at least 30 wt.-% and at most 95 wt.-%, preferably at least 40 wt.-% and at most 85 wt.-%, for example at least 45 wt.-% and at most 85 wt.-%, for example at least 50 wt.-% and at most 70 wt.-%, for example at least 55 wt.-% and at most 65 wt.-%, based on the total weight of the liquid composition according to the present invention, and wherein the total amount of all components constituting the liquid composition according to the present invention adds up to 100 wt.-%.

[0338] Preferably, the liquid composition according to the present invention comprises an organic solvent in an amount of at most 40 wt %, preferably at most 30 wt %, such as at most 25 wt %, such as at most 20 wt %, such as at most 12 wt %, such as at most 10 wt %, such as at most 8 wt %, such as at most 5 wt %, such as at most 4 wt %, such as 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 0.2 wt %, such as at most 0.1 wt %, based on the total weight of the liquid composition according to the present invention.

[0339] Preferably, the liquid compositions of the present invention contain no organic solvents.

[0340] Preferably, the liquid composition according to the present invention has a pH value, determined according to ISO 976:2013 and according to the description, 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 10 and at most 13, for example at least 10.5 and at most 12.0, for example at least 10.5 and at most 11.6, for example at least 10.5 and at most 11.5, with the proviso that the liquid composition according to the present invention comprises water in an amount of at least 20% by weight, preferably at least 25% by weight, more preferably at least 30% by weight, most preferably at least 35% by weight, based on the total weight of the liquid composition according to the present invention.

[0341] Preferably, the liquid composition according to the present invention 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) a mixture thereof, wherein the amount of 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%, based on the total weight of the AZ compound.

[0342] Preferably, the liquid composition according to the invention does not contain component T.

[0343] The liquid composition of the present invention may contain chloride. Preferably, 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 %, for example at most 0.05 wt %, for example at most 0.03 wt %, based on the total weight of the liquid composition of the present invention.

[0344] Preferably, the liquid compositions of the present invention are chloride-free.

[0345] Preferably, the liquid composition of the present invention further comprises:

[0346] iii) 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.

[0347] When the liquid composition of the present invention further comprises a polymer, as disclosed throughout the specification, the liquid composition of the present invention can be prepared by mixing a liquid medium, as disclosed throughout the specification, with AZ components, as disclosed throughout the specification, and a polymer, as disclosed throughout the specification. The mixing of the liquid medium, AZ components, and polymer can be carried out under standard conditions.

[0348] Preferably, the polymer is selected from the group consisting of polyesters, polyamides, polycarbonates, polyimides, alkyds, urethane-modified alkyds (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.

[0349] Preferably, the polymer is present in an amount of at least 5 wt% and at most 65 wt%, preferably at least 10 wt% and at most 60 wt%, more preferably at least 20 wt% and at most 55 wt%, for example at least 30 wt% and at most 50 wt%, based on the total weight of the aqueous composition, and wherein the total amount of all components constituting the mixture adds up to 100 wt%.

[0350] Preferably, the liquid composition of the present invention is a coating composition, preferably a liquid coating composition.

[0351] The liquid composition according to the invention may optionally (also) comprise further components, such as pigments and / or waxes, and / or customary (treatment) additives, such as degassing agents, if the liquid composition according to the invention is used for powder coatings, smoothing agents, appearance enhancers or (light) stabilizers. Suitable stabilizers include, for example, primary and / or secondary antioxidants and UV stabilizers, such as quinones, (sterically hindered) phenolic compounds, phosphonites, phosphites, thioethers and HALS (hindered amine light stabilizers). Examples of suitable degassing agents include cyclohexanedimethanol bisbenzoate, benzoin.

[0352] In yet another aspect, the present invention provides a solidified form of a liquid composition of the present invention - as disclosed throughout this specification.

[0353] The curing of the liquid composition 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 chemical reaction. The curing of the liquid composition of the present invention can be carried out under standard conditions (as these are defined in the specification), or by using heat, or by using pressure, or by applying a vacuum, or by radiation, such as radiation (e.g. ultraviolet (UV) radiation), or any combination thereof. Preferably, the liquid composition of the present invention can 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, preferably at most, of up to 60 minutes, more preferably at most 30 minutes, even more preferably at most 15 minutes.

[0354] The liquid compositions of the present invention can be cured in the presence of a cationic initiator.

[0355] The liquid composition of the present invention can be cured under standard conditions, for example for 12-48 h (preferably 24-48 h), in the presence of a suitable polymer (preferably used in aqueous dispersion) (e.g. 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), and / or by heat curing at 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 elevated temperature; an annealing step (e.g. 50° C. for 16 h) may also be included between the curing at elevated temperature and atmospheric pressure and the curing under standard conditions, wherein the annealing step is after the curing at elevated temperature and atmospheric pressure. Such liquid compositions according to the invention may 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 which may vary and is preferably at most 60 minutes, more preferably at most 30 minutes, even more preferably at most 15 minutes.

[0356] Obviously, curing at elevated temperature and atmospheric pressure requires shorter curing times; curing can also be achieved by the use of 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, alkyds, urethane-modified alkyds (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.

[0357] 4. Other aspects and embodiments of the present invention

[0358] In yet another aspect, the present invention provides a kit of parts comprising a part A and a part B that are physically separated from each other, wherein:

[0359] i) said part A comprises a liquid composition according to any one of A19 to A34 or any combination of the disclosures from subsections 1 and 3 and as disclosed throughout the specification, and

[0360] ii) part B comprises a polymer having an acid value in the range of 5 to 300 mg KOH / g, preferably 8 to 200 mg KOH / g, more preferably 10 to 150 mg KOH / g, determined according to ASTM D1639-90 (1996) e1, and wherein the polymer may optionally comprise ionic functional groups, and wherein the polymer is preferably selected from the group consisting of polyesters, polyamides, polycarbonates, polyimides, alkyds, urethane-modified alkyds (uralkyds), polyacrylics, polyurethanes, poly(urethane-acrylics) and mixtures thereof, more 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,

[0361] Part A does not contain the polymer of Part B, and Part B does not contain the liquid composition of Part A.

[0362] In yet another aspect, the invention provides a solidified form of an AZ component according to A1a or any one of A1 to A18 or any combination of the disclosures derived from subsections 1 and 3 and as disclosed throughout the specification, or a liquid composition according to any one of A19 to A34 or any combination of the disclosures derived from subsections 1 and 3 and as disclosed throughout the specification; preferably, the solidified form is a film.

[0363] In yet another aspect, the present invention provides an article comprising:

[0364] i) an AZ-component according to any one of A1a or A1 to A18 or any combination of the disclosures derived from subsection 1 and as disclosed throughout the specification, or ii) a liquid composition according to any one of A19 to A34 or any combination of the disclosures derived from subsections 1 and 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, imitation wood, leather, artificial leather, paper, fibers.

[0365] In yet another aspect, the present invention provides use of any one or any combination of the following as a cross-linking agent:

[0366] i) an AZ-component according to A1a or any one of A1 to A18 or derived from any combination of the disclosure in subsections 1 and 3 and as disclosed throughout the specification;

[0367] ii) A liquid composition according to any one of A19 to A34 or derived from any combination of the disclosure in subsections 1 and 3 and as disclosed throughout the specification.

[0368] In yet another aspect, the present invention provides 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:

[0369] i) AZ-components according to A1a or any one of A1 to A18 or any combination of the disclosures from subsection 1 and as disclosed throughout the specification;

[0370] ii) a liquid composition according to any one of A19 to A34 or any combination of the disclosures derived from subsections 1 and 3 and as disclosed throughout the specification;

[0371] iii) a kit of parts according to A35 or derived from any combination of the disclosure in subsections 1 and 3 and as disclosed throughout this specification;

[0372] iv) a solidified form according to any one of A36 to A37 or any combination of the disclosures derived from subsections 1 and 3 and as disclosed throughout the specification;

[0373] v) An article according to any one of A38 to A39 or derived from any combination of the disclosure in subsections 1 and 3 and as disclosed throughout the specification.

[0374] Furthermore, another aspect of the present invention is any of the AZ-components shown in the examples according to the present invention (Example 1, Example 2, Example 3 and Example 4).

[0375] Furthermore, another aspect of the present invention is any one of the liquid compositions shown in the Examples (Example 1, Example 2, Example 3, and Example 4) according to the present invention.

[0376] Many other variations and embodiments of the invention will be apparent to those skilled in the art, and such variations are within the scope of the invention.

[0377] Any features, elements, components, embodiments, ranges and in particular any preferred features, preferred elements, preferred embodiments, preferred ranges, combinations of preferred ranges, preferences described throughout the specification may be combined with each other.

[0378] Further aspects of the invention and preferred features thereof are given in the description.

[0379] The invention will now be described in detail by reference to the following illustrative, non-limiting examples. Example

[0380] The present invention is explained in more detail with reference to the following non-limiting examples.

[0381] Unless explicitly stated otherwise, all examples presented in this subsection were conducted in a controlled laboratory environment under standard conditions (as these are defined in this specification), 50±1% relative humidity and ≤0.1 m / s airflow.

[0382] 1.1 Chemicals, raw materials and other materials

[0383] Triethylamine (99.7% purity) was supplied by ARKEMA. Propyleneimine (≥99.0% purity) was supplied by Menadiona. Anhydrous potassium carbonate (K2CO3; ≥99.0% purity) was supplied by Alfa Aesar. Trimethylolpropane tris(2-methyl-1-aziridine propionate) (CAS No. 64265-57-2; see structure in Example 1C) was supplied by DSM (trade name 'Crosslinker CX-100'). N 3600 is a low-viscosity aliphatic polyisocyanate (trimer) 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 (hazen): ≤ 40 (M017 - EN 1557);

[0384] Monomeric HDI: ≤0.25% (M106-ISO 10283); equivalent weight: about 183; flash point: about 159° C. (DIN 53213 / 1); density at 20° C.: about 1.16 g / ml (DIN EN ISO 2811), supplied by Covestro. N 3900 is a low-viscosity aliphatic polyisocyanate 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 (hazen): ≤40 (M017-EN 1557); monomeric HDI: ≤0.25% (M106-ISO 10283); equivalent weight: about 179; flash point: about 203°C (DIN 53213 / 1); density at 20°C: about 1.15 g / ml (DIN EN ISO 2811), supplied by Covestro. GE-36 is a triglycidyl ether of propoxylated glycerol (see Scheme 1) (EEW: 620-680 g / 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) (epoxide equivalent weight (EEW): 95-110 g / 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 difunctional glycidyl ether epoxy resin (see Scheme 3) [reddish-brown liquid; color (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 loss (wt%): ≤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 (Gardner): maximum 2), supplied by CVC Thermoset Specialties (now HUNSTMAN). Bisphenol A diglycidyl ether (CAS No. 1675-54-3) was supplied by Tokyo Chemical Industry Co., Ltd. N,N-diglycidyl-4-glycidyloxyaniline (CAS No. 5026-74-4) was supplied by Sigma-Aldrich. Methyl ethyl ketone was 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 were supplied by DOW. DOWAN Olg KOH / glycol ether [dipropylene glycol monomethyl ether; CAS number: 34590-94-8; boiling point: 190°C at 760 mmHg; density: 0.948 g / mL; flash point (closed cup): 75°C; freezing point: -83°C; molecular weight: 148.2 Da; specific gravity (25°C): 0.951; surface tension: 28 dynes / cm; viscosity (25°C): 3.7 cP; vapor pressure (20°C): 0.28 mmHg; solubility in water (25°C): infinite (wt%)] is a (medium to slow evaporating) organic solvent. Any other chemicals not explicitly mentioned in this paragraph and used in the Examples section (and unless otherwise stated in the specification) have been supplied by Sigma-Aldrich.

[0385]

[0386]

[0387] 1.2 Preparation of polyurethane A and its aqueous dispersion (the latter abbreviated as 'polyurethane A-AQD')

[0388] A 1-liter flask (equipped with a thermometer and an overhead stirrer) was charged with 29.9 grams of dimethylolpropionic acid, 282.1 grams of calculated number average molecular weight (M n ) is 2000Da and the OH value is 56±2mgKOH / g polypropylene glycol), 166.5g calculated number average molecular weight (M n) of 1000 Da and an OH value of 112 ± 2 mg KOH / g polypropylene glycol, and 262.8 grams of isophorone diisocyanate (the number average molecular weight of each of the polyols is calculated from its OH value according to the following formula: M n = 2*56100 / [OH number in mg KOH / g polypropylene glycol]. The reaction mixture was placed under an N2 atmosphere and heated to 50°C, followed by the addition of 0.07 g of dibutyltin dilaurate. An exothermic reaction was observed; however, appropriate measures were required to prevent the reaction temperature from exceeding 97°C. The reaction was maintained at 95°C for one hour. The resulting polyurethane A had an NCO content of 7.00% (theoretical 7.44%) based on solids, as determined according to ISO 14896, Method A (2009), and an acid number of 16.1±1 mg KOH / g polyurethane A. Polyurethane A was cooled to 60°C, 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: a mixture of polyurethane A prepared in this manner and triethylamine was added to a mixture of 1100 g of demineralized water, 19.5 g of nonylphenol ethoxylate (9 ethoxylate groups), and 4.0 g of triethylamine at room temperature over a period of 60 minutes. After the addition was complete, the mixture was stirred for an additional 5 minutes, after which 111.2 g of hydrazine (16% by weight aqueous solution) was added to the mixture. The aqueous dispersion of polyurethane A prepared in this manner was stirred for an additional 1 hour.

[0389] 1.2 Molecular Weight Determination of Compounds AZ1 to AZ5 and Component T (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometry; MALDI-TOF MS)

[0390] All MALDI-ToF-MS spectra were obtained using Bruker UltrafleXtreme TMMALDI-ToF mass spectrometer is obtained. This instrument is equipped with Nd:YAG laser and collision cell (not used for these samples) that emit at 1064nm. Use reflectron, use the highest resolution mode (scope is 60-7000m / z) that provides accurate mass to obtain spectrum with positive ion mode. Use cesium triiodide (scope is 0.3-3.5kDa) to carry out mass calibration (calibration method: IAV molecular characterization, code MC-MS-05). Laser energy is 20%. Sample is dissolved in THF with about 50mg / mL. The matrix used is: DCTB (trans 2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene] malononitrile), CAS number 300364-84-5. Prepare matrix solution by 20mg being dissolved in 1mL THF. Potassium trifluoroacetate (KTFA, CAS No. 2923-16-2) or, alternatively, sodium iodide (NaI, CAS No. 7681-82-5) was used as the salt; 10 mg was dissolved in 1 ml of THF with a drop of MeOH. The sample:matrix:salt ratio was 10:200:10 (μL). After mixing, 0.5 μL was spotted onto a MALDI plate and air-dried for 20 min. The reported signal is the main peak within 0.5 Da of the calculated mass of the polyaziridine compound theoretically present in the composition at its maximum amount. In all cases, the reported peak is the sodium or potassium adduct of the measured ion. The reported MALDI-TOF MS signal corresponds to the main peak of the sodium or potassium adduct of the measured ion (sodium and potassium cations) 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 as 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.

[0391] Polyaziridine compounds are identified by comparing the molecular weight (MW) defined just below 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 formula:

[0392] MW = observed [M + M 阳离子 ]-[M 阳离子 ]

[0393] in

[0394] M 阳离子is the exact molar mass of the sodium (22.99 Da) or potassium cation (38.96 Da) (depending on which cation is used in the MALDI-TOFMS method), and

[0395] Observed [M+M 阳离子 ] is a MALDI-TOF MS signal (peak), which corresponds to the theoretical formula of the polyaziridine compound.

[0396] 1.3 Determination of genotoxicity ( Determination)

[0397] Genotoxicity was assessed according to the ToxTracker assay (Toxys, Leiden, the Netherlands) as follows. The assay can be applied to pure substances or to compositions obtained as direct products during the preparation of compounds bearing an aziridine ring.

[0398] The ToxTracker assay is a set of several validated green fluorescent protein (GFP)-based mouse embryonic stem (mES) reporter cell lines that can be used to identify the bioactivity and potential oncogenic properties of newly developed compounds in a single test. The method uses a two-step approach.

[0399] In the first step, a dose range study was performed using wild-type mES cells (line B4418). 20 different concentrations of each compound were tested, starting with 10 mM in DMSO as the highest concentration, and 19 serial 2-fold dilutions. Next, the genotoxicity of the samples (Examples of the present invention and Comparative Examples) was assessed using specific genes linked to reporter genes for detecting DNA damage; the reporter genes were Bscl2 (as described by US9695481B2 and EP2616484B1) and Rtkn (Hendriks et al., Toxicol. Sci. 2015, 150, 190-203) biomarkers. Genotoxicity was assessed at 10%, 25%, and 50% cytotoxicity in the absence and presence of a metabolic system based on rat S9 liver extract (aroclor1254-induced rats, Moltox, Boone, NC, USA). Independent cell lines were seeded into 96-well cell culture plates, and 24 hours after the cells were seeded into the 96-well plates, fresh ES cell culture medium containing the diluted test substance was added to the cells. For each test compound, five concentrations were tested with 2-fold dilution. The highest sample concentration will induce significant cytotoxicity (50-70%). In the case of no or low cytotoxicity, 10mM or maximum soluble mixture concentration was used as the maximum test concentration. Cytotoxicity was determined by counting cells using a Guava easyCyte 10HT flow cytometer (Millipore) after 24 hours of exposure. GFP reporter gene induction was always compared with vehicle control treatment. For specific compounds, the DMSO concentration in all wells was similar and never exceeded 1%. All compounds were tested in at least three completely independent replicates. All experiments included a positive control treatment (DNA damage) using cisplatin. Metabolism was assessed by adding S9 liver extract. In the presence of S9 and the required cofactor (RegenSysA+B, Moltox, Boone, NC, USA), cells were exposed to five concentrations of test compounds for 3 hours. After washing, the cells were incubated in fresh ES cell culture medium for 24 hours. After exposure for 24 hours, the induction of the GFP reporter gene was determined using a Guava easyCyte 10HT flow cytometer (Millipore). Only the GFP expression in intact individual cells was determined. The average GFP fluorescence and cell concentration in each well were measured and used for cytotoxicity assessment. Data were analyzed using ToxPlot software (Toxys, Leiden, the Netherlands). The reported induction levels were in the presence of S9 rat liver extracts, exposed for 3 hours and recovered for 24 hours, or alternatively, in the absence of S9 rat liver extracts, exposed for 24 hours to induce 10%, 25%, and 50% cytotoxicity at a compound concentration.A positive induction level of a biomarker is defined as equal to or higher than 2-fold induction at at least one of 10%, 25% and 50% cytotoxicity in the absence or presence of a metabolic system rat S9 liver extract; a weak positive induction is defined as higher than 1.5-fold and lower than 2-fold induction at at least one of 10%, 25% and 50% cytotoxicity in the absence or presence of a metabolic system rat S9 liver extract (but lower than 2-fold at 10%, 25% and 50% cytotoxicity), and a negative induction is defined as lower than or equal to 1.5-fold induction at 10%, 25% and 50% cytotoxicity in the absence or presence of a metabolic system based on rat S9 liver extract. In the context of this specification, "non-genotoxic" (or equivalently "not genotoxic") means that the induction level shown in the absence and presence of a rat S9 liver extract-based metabolic system (aroclor1254-induced rat, Moltox, Boone, NC, USA) at 10%, 25% and 50% cytotoxicity is less than 2 times, preferably equal to or less than 1.9 times, more preferably equal to or less than 1.8 times, for example equal to or less than 1.7 times, for example equal to or less than 1.6 times, for example equal to or less than 1.5 times.

[0400] 1.4 Evaluation of cross-linking efficiency

[0401] The cross-linking efficiency of the organic compound having an aziridine ring in the liquid composition [or similarly the cross-linking efficiency of the liquid composition comprising the organic compound having an aziridine ring] was evaluated by measuring the chemical resistance of the film (cured coating).

[0402] The chemical resistance of the film (cured coating) was tested based on DIN 68861-1:2011-01. The film was prepared as follows: 0.43 parts of the composition were mixed with 0.57 parts of DOWANOL TM The mixture was stirred for 10 minutes at 80°C and stirred for 10 minutes. Subsequently, a certain amount of the resulting solution was added to a certain amount of polyurethane A-AQD under continuous stirring, and the resulting mixture was stirred for another 30 minutes to prepare a liquid composition. These amounts were calculated based on a molar ratio of 0.9 of the number of moles of aziridine rings present in an organic compound (e.g., AZ component) (or a mixture of organic compounds) having an aziridine ring to the number of moles of carboxylic acid functional groups present in polyurethane A. This liquid composition was filtered and subsequently applied to a Leneta test card using a 100 μm wire coater. The film was dried at 25°C for 16 hours, then annealed at 50°C for 1 hour and then dried at 25°C for 24 hours.

[0403] Cotton pads (1 x 1 cm) were soaked in a 1:1 ethanol:demineralized water solution. These were then placed on the membrane and covered with a Petri dish for 240 minutes. Afterwards, the pads and Petri dish were removed, and after 1 hour, the coating was visually inspected for damage. The degree of damage was rated according to the following rating scheme:

[0404] 5: No visible changes

[0405] 4: There is almost no noticeable change in gloss or color

[0406] 3: Slight gloss or color change; no structural change on the test surface

[0407] 2: Significant changes are evident; however, the structure of the test surface remains more or less intact.

[0408] 1: Significant change is evident; the structure of the test surface has changed.

[0409] 0: The tested surface is severely altered or damaged.

[0410] In the context of this specification, the above integers 0-5 are referred to as 'rating points'.

[0411] The chemical resistance of the reference film (made only from polyurethane A-AQD) is poor (this applies to all inventive and comparative examples shown in the examples).

[0412] 1.5 pH determination

[0413] The pH of the samples was determined according to ISO 976:2013. The samples were measured at room temperature using a Metrohm 691 pH meter equipped with a combined glass electrode and a PT-1000 temperature sensor. The pH meter was calibrated prior to use using buffer solutions of pH 7.00 and 9.21.

[0414] 1.6 Determination of acid value

[0415] The acid value of a polymer is determined according to ASTM D1639-90 (1996) e1. According to the procedure, a sample dissolved in a good solvent is titrated with an alcoholic potassium hydroxide solution of known concentration (KOH). The difference in titration volume between the sample and the blank is a measure of the solid's acid value according to the following formula:

[0416] AV=[(V 空白 -V 样本 )*N KOH *56.1] / (W*S / 100)

[0417] in

[0418] AV is the solid acid value in mg KOH / g solid material, V空白 is the volume of KOH solution used in the blank, V 样本 is the volume of 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 solids content of the sample in %. The measurements were performed in duplicate using a potentiometric endpoint on a Metrohm 702SM Titrino titrator (the results were accepted if the difference between the duplicates was <0.1 mg KOH / g solid matter).

[0419] 1.7 Determination of NCO content

[0420] The NCO content of the samples was determined according to ASTM D2572-19. In this procedure, the sample is reacted with an excess of n-dibutylamine. The excess n-dibutylamine is then back-titrated with standard 1N hydrochloric acid (HCl). The difference in titration volume between the sample and the blank is a measure of the isocyanate content based on solids, according to the following formula:

[0421] %NCO 固体 =[(V b -V m )*N*4.2] / (A*s / 100)

[0422] in

[0423] %NCO 固体 isocyanate content based on solids, V b is the volume of HCl used in the blank, V m is the volume of HCl used in the sample, N is the normality of the HCl solution, A is the sample weight in grams, and s is the solids content of the sample in %. The measurements were performed in duplicate on a Metrohm 702SM Titrino titrator using the potentiometric endpoint (if the difference between the duplicates was <0.1% NCO , then accept the measurement result).

[0424] 1.8 Determination of the Amount of Component T [Liquid Chromatography-Mass Spectrometry (LC-MS)]

[0425] The amount of component T (as the latter is defined in this specification; % by weight relative to the total weight of the AZ compounds) is determined by liquid chromatography coupled to 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 ultrahigh pressure liquid chromatography (UHPLC) system equipped with: a) a HPLC system operated at 40°C; The HPLC-MS / MS was carried out using a high strength silica gel (HSS) technology C18 type T3 column [100×2.1 mm (length×diameter); 1.8 μm average particle size stationary phase] supplied by Agilent 6550iFunnel QTOF detector [electrospray ionization-time of flight mass spectrometry (ESI-TOF-MS) detector]. Once the sample was injected, a mobile phase gradient [from 80 / 20 v / v A / B to 1 / 99 v / v A / B, where A was 10 mM CH3COO] was applied at a flow rate of 0.5 mL / min. - 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 mobile phase gradient [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 the entire response range and that all components of the sample have equal ionization efficiency, the signals of the following substances are integrated:

[0426] - total ion current, and

[0427] -Extracted ion chromatogram of component T.

[0428] Data acquisition was performed by MassHunter Build 10.1.48 software supplied by Agilent, and data processing was performed by Qualitative Analysis Build 10.0.10305.0 software also supplied by Agilent.

[0429] The amount of component T (weight % based on the total weight of the AZ compound) is determined by dividing the integral of the extracted ion chromatogram of component T by the integral of the total ion current, multiplied by 100.

[0430] 1.9 Determination of the amount of chloride

[0431] The amount of chloride in the liquid composition was determined according to ASTM D1726-11 (2019).

[0432] 2. Embodiments of the Invention

[0433] Example 1

[0434] 100g GE-36, 26.5 g of propylene imine and 5 g of potassium carbonate were placed in a reaction flask equipped with a thermometer and a condenser connected to a low temperature thermostat (3°C). The mixture was stirred with a mechanical upper stirrer under a nitrogen atmosphere. The mixture was then heated to 80°C. Samples were taken at regular intervals and the mixture was heated using a 1 The reaction progress was monitored by H-NMR until no signals (chemical shifts) were observed related to the epoxidized protons from the multifunctional epoxide. The reaction mixture was diluted with toluene and filtered. The solvent and excess propylene imine were removed in vacuo from the filtrate to obtain a clear, high-viscosity liquid. The theoretical formula of the (aziridinyl hydroxyl)-functional organic compound thus prepared is shown below (wherein x+y+z=33), and the theoretical molecular weight was calculated to be 2346.68 Da.

[0435]

[0436] The molecular weight determined by MALDI-TOF MS—as defined and described herein—is 2346.50 Da (observed [M+M Na+ ]-[M Na+ ]).

[0437] The crosslinking efficiency of the (aziridine hydroxy)-functional organic compounds (and their liquid compositions) obtained above is very good, considering the genotoxicity shown in the following table. The test results showed that this (aziridine hydroxy)-functional organic compound has no genotoxicity.

[0438]

[0439] Example 2

[0440] 75 grams of 9000 was dissolved in 75 mL of toluene and loaded into a reaction flask equipped with a thermometer and a condenser connected to a low temperature thermostat (3°C). Next, 55 grams of propylene imine and 5 grams of potassium carbonate were added to the flask. The mixture was stirred with a mechanical upper stirrer under a nitrogen atmosphere. The mixture was then heated to 80°C. Samples were taken at regular intervals and used 1 The reaction mixture was stirred for 24 hours at room temperature for 1 hour.Then the ...

[0441]

[0442] The molecular weight determined by MALDI-TOF MS—as defined and described herein—is 645.37 Da (observed [M+M Na+ ]-[M Na+ ]).

[0443] The crosslinking efficiency of the (aziridine hydroxy)-functional organic compounds (and their liquid compositions) obtained above is very good, considering the genotoxicity shown in the following table. The test results showed that this (aziridine hydroxy)-functional organic compound has no genotoxicity.

[0444]

[0445] Example 3

[0446] 130 grams of N 3600 was dissolved in 130 grams of toluene, loaded into a reaction flask equipped with a thermometer and heated to 50°C. Next, 0.05 grams of triethylamine was added to the flask and 52 grams of glycidol was slowly added to the reaction mixture over a period of 90 minutes, while ensuring that the reaction temperature remained constant between 55-58°C. After stirring at this temperature for another 60 minutes, the mixture was cooled to room temperature and stirred at room temperature for 18 hours. The solvent was removed in vacuo, and the resulting light yellow oil was transferred to a reaction flask equipped with a thermometer and a condenser connected to a low-temperature thermostat (3°C). Next, 200 grams of toluene, 150 grams of propylene imine and 5 grams of potassium carbonate were added to the flask. The mixture was stirred with a mechanical upper stirrer under a nitrogen atmosphere. The mixture was then heated to 60°C. Samples were taken at regular intervals and the mixture was analyzed using a 40-well plate. 1 The reaction mixture is stirred 18 hours at 4 ℃ for 2 hours.H-NMR monitors reaction process, until observing and can not be relevant with the epoxidation proton from multifunctional epoxide signal (chemical shift).After reacting for 18 hours, mixture is filtered.From filtrate, vacuum removal solvent and excessive propylene imine, to obtain high viscosity liquid.The theoretical formula of (aziridinyl hydroxyl)-functional organic compound prepared thus is as follows, and theoretical molecular weight is calculated to be 897.55Da.

[0447]

[0448] The molecular weight determined by MALDI-TOF MS—as defined and described herein—is 897.58 Da (observed [M+M Na+ ]-[M Na+ ]).

[0449] The crosslinking efficiency of the (aziridine hydroxy)-functional organic compounds (and their liquid compositions) obtained above is very good, considering the genotoxicity shown in the following table. The test results showed that this (aziridine hydroxy)-functional organic compound has no genotoxicity.

[0450]

[0451] Example 4

[0452] 30.0 g NC-514S, 19.2 g of propylene imine, 30 g of toluene and 3 g of potassium carbonate were placed in a reaction flask equipped with a thermometer and a condenser connected to a low-temperature thermostat (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 regularly and used 1 The reaction mixture is stirred 2 hours at 4 ℃ for 1 hour.H-NMR monitors reaction process, until not observing the signal (chemical shift) relevant with the epoxidation proton from multifunctional epoxide.After reacting 20 hours, the mixture is diluted with toluene and filtered.Vacuum removes solvent and excessive propylene imine from filtrate, obtains high viscosity brown oil.The theoretical formula of (aziridine hydroxyl)-functional organic compound prepared in this way is as follows, and theoretical molecular weight is calculated to be 622.47Da.

[0453]

[0454] The molecular weight determined by MALDI-TOF MS—as defined and described herein—is 622.43 Da (observed [M+M Na+ ]-[M Na+ ]).

[0455] The crosslinking efficiency of the (aziridine hydroxy)-functional organic compounds (and their liquid compositions) obtained above is very good, considering the genotoxicity shown in the following table. The test results showed that this (aziridine hydroxy)-functional organic compound has no genotoxicity.

[0456]

[0457] 3. Comparative Example

[0458] Example 1C

[0459] Trimethylolpropane tris(2-methyl-1-aziridine propionate) (trade name 'crosslinker CX-100') has the following structure:

[0460]

[0461] And the theoretical molecular weight was calculated to be 467.30 Da.

[0462] The crosslinking efficiency of trimethylolpropane tris(2-methyl-1-aziridine propionate) (and its liquid composition) is very good, considering the genotoxicity shown in the following table The test results showed that trimethylolpropane tris (2-methyl-1-aziridine propionate) is genotoxic.

[0463]

[0464] Example 2C

[0465] 75g GA-240, 80 g of propylene imine 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 upper stirrer under a nitrogen atmosphere. The mixture was then heated to 71 ° C. Samples were taken regularly and 1 The reaction was carried out under reduced pressure, and the reaction mixture was stirred for 2 hours. The reaction mixture was stirred for 2 hours. The reaction mixture was stirred for 2 hours. The reaction mixture was stirred for 3 hours. The reaction mixture was stirred for 3 hours. The reaction mixture was stirred for 2 hours. The reaction mixture was stirred for 3 hours. The reaction mixture was stirred for 3 hours. The reaction mixture was stirred for 3 hours. The reaction mixture was stirred for 4 hours. The reaction mixture was stirred for 3 hours. The reaction mixture was stirred for 4 hours. The reaction mixture was stirred for 3 hours.

[0466]

[0467] The molecular weight determined by MALDI-TOF MS—as defined and described herein—is 588.48 Da (observed [M+M Na+ ]-[M Na+ ]).

[0468] The cross-linking efficiency of the (aziridine hydroxy)-functional organic compound (and its liquid composition) obtained above is good, considering the genotoxicity shown in the following table. The test results showed that this polyaziridine compound is genotoxic.

[0469]

[0470] Example 3C

[0471] 24.0 g of N,N-diglycidyl-4-glycidyloxyaniline, 42.0 g of propylene imine, 30 g of toluene and 3 g of potassium carbonate were placed in a reaction flask equipped with a thermometer and a condenser connected to a low-temperature thermostat (3-temperature thermostat). The mixture was stirred with a mechanical stirrer under a nitrogen atmosphere. The mixture was then heated to 70°C. Samples were taken regularly and used1 In 40mL ethyl aziridine ether, 4-nitropropene sulfonate is added in 4% paraformaldehyde, 4-nitropropene sulfonate and 4-nitropropene sulfonate.H-NMR monitors reaction process, until not observing the signal (chemical shift) relevant with the epoxidation proton from multifunctional epoxide.After reacting for 24 hours, the mixture is diluted with toluene and filtered.Vacuum removes solvent and excessive propylene imine from filtrate, obtains the yellow material of height viscosity.The theoretical molecular formula of the many aziridine compounds prepared in this way is as follows, and theoretical molecular weight is calculated to 448.30Da.

[0472]

[0473] The molecular weight determined by MALDI-TOF MS—as defined and described herein—is 488.30 Da (observed [M+M Na+ ]-[M Na+ ]).

[0474] This compound is disclosed in cl.2, ll.29-39 of US 3329674.

[0475] The cross-linking efficiency of the (aziridine hydroxy)-functional organic compound (and its liquid composition) obtained above is good, considering the genotoxicity shown in the following table. The test results showed that this polyaziridine compound is genotoxic.

[0476]

[0477] Example 4C

[0478] 299 g of bisphenol A diglycidyl ether, 250 g of toluene, 255 g of propylene imine and 10 g of potassium carbonate were placed in a reaction flask equipped with a thermometer and a condenser connected to a low-temperature thermostat (3°C). The mixture was stirred with a mechanical upper stirrer under a nitrogen atmosphere. The mixture was then heated to 70°C. Samples were taken regularly and the progress of the reaction was monitored using 1H-NMR until no signals (chemical shifts) associated with epoxide protons from the multifunctional epoxide were observed. After reacting for 19 hours, the mixture was filtered. The solvent and excess propylene imine were removed from the filtrate in vacuo to obtain a high-viscosity liquid. The theoretical molecular formula of the polyaziridine compound prepared in this way is shown below, and the theoretical molecular weight is calculated to be 454.28 Da.

[0479]

[0480] The molecular weight determined by MALDI-TOF MS—as defined and described herein—is 454.26 Da (observed [M+M Na+ ]-[M Na+ ]).

[0481] The cross-linking efficiency of the (aziridine hydroxy)-functional organic compound (and its liquid composition) obtained above is good, considering the genotoxicity shown in the following table. The test results showed that this polyaziridine compound is genotoxic.

[0482]

[0483] 4. Conclusion

[0484] US Pat. No. 3,329,674 to Thiokol Chemical Corporation discloses low molecular weight aziridine derivatives of polyfunctional epoxides. As described in the specification, the molecular weights of these aziridine derivatives are well below 600 Da. US Pat. No. 3,329,674 discloses no (aziridine hydroxy)-functional organic compounds having molecular weights of at least 600 and at most 10,000 Da. US Pat. No. 3,329,674 fails to provide (aziridine hydroxy)-functional organic compounds (and liquid compositions thereof) that are non-genotoxic and at least have good crosslinking efficiency. Evidence of this is shown in Example 3C, which is genotoxic.

[0485] When comparing the results of inventive examples 1 to 4 and comparative examples 1C to 4C, it is clear that only the inventive AZ-components (and the inventive liquid compositions) are not genotoxic and have at least a good crosslinking efficiency.

Claims

1. An AZ component, which is an (aziridinylhydroxy)-functional organic component selected from the group consisting of: i) an (aziridinylhydroxy)-functional organic compound AZ1 of formula A1 having only two aziridine rings, referred to as AZ1 compound, ii) an (aziridinylhydroxy)-functional organic compound AZ2 of formula A2 having only three aziridine rings, referred to as AZ2 compound, iii) an (aziridinylhydroxy)-functional organic compound AZ3 of formula A3 having only four aziridine rings, referred to as AZ3 compound, iv) an (aziridinylhydroxy)-functional organic compound AZ4 of formula A4 having only five aziridine rings, referred to as AZ4 compound, v) an (aziridinylhydroxy)-functional organic compound AZ5 of formula A5 having only six aziridine rings, referred to as AZ5 compound, and vi) a mixture thereof. in 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 collection of atoms covalently linked in a configuration comprising linear and / or branched and / or cyclic structures, said collection of atoms being selected from the group consisting of i) to x) 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 viiii), and wherein each of said X1 to X5 has a carbon atom and a hydrogen atom, and wherein each of said X1 to X5 optionally has an oxygen atom and / or a nitrogen atom and / or a sulfur atom and / or a silicon atom, and wherein said X1 and / or said X2 and / or said X3 and / or said X4 and / or said X5 optionally contain an ionic functional group, And among them each of said X1 to X5 comprises only single covalent bonds, or both single covalent bonds and double covalent bonds, and wherein the single covalent bond is selected from the group consisting of a carbon-carbon single bond, a carbon-hydrogen single bond, a carbon-nitrogen single bond, a carbon-sulfur single bond, a carbon-silicon single bond, a silicon-oxygen single bond, a nitrogen-hydrogen single bond, a carbon-oxygen single bond in which oxygen is bonded to hydrogen to form a hydroxyl group, a silicon-oxygen-silicon single bond, and wherein the double covalent bond is selected from the group consisting of a carbon-carbon double bond, a carbon-nitrogen double bond, a carbon-oxygen double bond in which carbon is a member of a ring structure, and a carbon-oxygen double bond in which carbon is bonded to two other carbons through a carbon-carbon single bond, a carbon-oxygen double bond in which carbon is bonded to another oxygen and to nitrogen through a single bond, a carbon-oxygen double bond in which carbon is bonded to two nitrogens through a carbon-nitrogen single bond, and a carbon-oxygen double bond in which carbon is bonded to two other oxygens through a single bond, in 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, And among them 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 among them Y in each of said compounds A1 to A5 is 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 a carbon-carbon single bond and a carbon-oxygen single bond, and wherein each of the compounds AZ1 to AZ5 has a molecular weight of at least 600 Da and at most 5000 Da as determined by MALDI-TOF MS, and wherein The X1 and / or the X2 and / or the X3 and / or the X4 and / or the X5 do not include one or any combination of the following structural units BP1, BP2, BP3 and BS 2. The AZ component according to claim 1, 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: in R' is selected from the group consisting of: hydrogen and methyl; and j is an integer ranging from 1 to 5; and n is an integer in the range from and including 2 up to and including 50.

3. The AZ group molecule according to any one of claims 1 to 2, wherein the aggregate number of carbon atoms in R1, R2, R3 and R4 is at most 9.

4. The AZ component according to any one of claims 1 to 2, wherein X1 is a divalent aliphatic organic group of formula A1a' in R' is selected from the group consisting of: hydrogen and methyl; and j is an integer ranging from 1 to 5; and n is an integer in the range from and including 2 up to and including 50.

5. The AZ component according to any one of claims 1 to 2, wherein each of X1 to X5 comprises only single covalent bonds, or both single and double covalent bonds, and wherein the single covalent bond is selected from the group consisting of a carbon-carbon single bond, a carbon-hydrogen single bond, a carbon-nitrogen single bond, a carbon-sulfur single bond, a carbon-silicon single bond, a silicon-oxygen single bond, a nitrogen-hydrogen single bond, a carbon-oxygen single bond in which oxygen is bonded to hydrogen to form a hydroxyl group, a silicon-oxygen-silicon single bond, and wherein the double covalent bond is selected from the group consisting of a carbon-carbon double bond, a carbon-nitrogen double bond, a carbon-oxygen double bond in which carbon is a member of a ring structure, and a carbon-oxygen double bond in which carbon is bonded to two other carbons through a carbon-carbon single bond, a carbon-oxygen double bond in which carbon is bonded to another oxygen through a single bond and to nitrogen through a single bond, and a carbon-oxygen double bond in which carbon is bonded to two nitrogens through a carbon-nitrogen single bond.

6. The AZ component according to any one of claims 1 to 2, wherein the AZ component is selected from the group consisting of: i) an AZ1 compound, ii) an AZ2 compound, iii) an AZ3 compound, iv) an AZ5 compound, and vi) a mixture thereof, and in 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 as follows wherein each of said n in Formula A1a is independently selected, and each of said n 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 C3-C 10 a saturated alkylene group, and wherein each of said n in Formula A1b is independently selected, and each of said n in Formula A1a is an integer within the range of from and including 2 up to and including 20; and wherein each of said n in Formula A1c 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 R in formula A1d is C3-C 10 a 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 within the range of from and including 2 up to and including 20; and in 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 which is described below. wherein n in Formula A2a is an integer ranging from and including 2 up to and including 20; and wherein each of said n in Formula A2b is independently selected, and each of said n in Formula A2b is an integer in the range from and including 2 up to and including 20; and wherein each of said n in Formula A2c is independently selected, and each of said n in Formula A2c is an integer in the range from and including 2 up to and including 20; and and and in The AZ3 compound is selected from the group consisting of: a compound having formula A3a wherein each of said n in Formula A3a is independently selected, and each of said n in Formula A3a is an integer in the range from and including 2 up to and including 20; and in The AZ5 compound is selected from the group consisting of: a compound having formula A5a wherein each of the n in Formula A5a is independently selected, and each of the n in Formula A5a is an integer in the range from and including 2 up to and including 40.

7. The AZ component according to any one of the preceding 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 formula, 8. The AZ component according to any one of the preceding 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 formula, 9. The AZ component according to any one of the preceding 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 formula, 10. The AZ component according to any one of the preceding 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 formula, 11. The AZ component according to any one of the preceding claims 1 to 2, wherein the AZ component is selected from the group consisting of an AZ1 compound, an AZ2 compound or a mixture thereof, and wherein the AZ1 compound is a compound of the formula, And wherein the AZ2 compound is selected from the group consisting of compounds of the following formula, 12. A liquid composition comprising: i) a liquid medium selected from the group consisting of organic solvents, water, and mixtures thereof, in an amount of up to 90% by weight based on the total weight of the liquid composition; and ii) the AZ component of any one of claims 1 to 11; and The total amount of all components constituting the liquid composition adds up to 100 wt%.

13. The liquid composition according to claim 12, wherein the liquid composition has a pH value of at least 7.5 and at most 14.0 determined according to ISO 976:2013, provided that the liquid composition comprises water in an amount of at least 20% by weight, based on the total weight of the liquid composition.

14. The liquid composition according to claim 12, wherein the liquid composition 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 and comprising at least one aziridine ring, and ii) a mixture thereof, wherein the amount of component T as determined by liquid chromatography coupled to mass spectrometry is at most 5 wt%, based on the total weight of the AZ component.

15. The liquid composition according to claim 12, further comprising iii) a polymer having an acid value of at least 5 mg KOH / g and at most 300 mg KOH / g, determined according to ASTM D 1639-90 (1996) e1, and wherein the polymer optionally comprises ionic functional groups.

16. A kit of parts comprising a part A and a part B that are physically separated from each other, wherein: i) the part A comprises the liquid composition according to any one of claims 12 to 15, and ii) said part B comprises 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 said polymer optionally comprises ionic functional groups, and Part A does not contain the polymer of Part B, and Part B does not contain the liquid composition of Part A.

17. A solidified form of the AZ component according to any one of claims 1 to 11 or the liquid composition according to any one of claims 12 to 15.

18. An article selected from the group consisting of textiles, glass, metal, composites, plastics, wood, engineered wood, imitation wood, leather, artificial leather, paper and fibers, the article comprising: i) the AZ component according to any one of claims 1 to 11, and / or ii) the liquid composition according to any one of claims 12 to 15, and / or ii) the solidified 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, manufacturing medical compositions, manufacturing medical devices: i) an AZ component according to any one of claims 1 to 11; ii) a liquid composition according to any one of claims 12 to 15; iii) The kit of parts according to claim 16; iv) a cured form according to claim 17; v) The article according to claim 18.

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