Aziridinyl-functional organic compounds
Aziridinyl-functional organic compounds improve the ER, RWR, and WR of coatings, addressing the limitations of existing coatings by enhancing their resistance to ethanol, red wine, and water.
Patent Information
- Application Number
- PCT/EP2025/073579
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-08-20
- Filing Date
- 2025-08-18
- Publication Date
- 2026-02-26
AI Technical Summary
Existing coatings lack enhanced ethanol resistance (ER) and often fail to combine this property with red wine resistance (RWR) and water resistance (WR), posing a significant challenge in the coatings industry.
The development of aziridinyl-functional organic compounds, which when incorporated into coating compositions, enhance ER, RWR, and WR, providing coatings with improved resistance to ethanol, red wine, and water.
The aziridinyl-functional organic compounds significantly enhance the ER, RWR, and WR of coatings, achieving ratings of at least 4, preferably 5, in standard testing protocols.
Smart Images

Figure EP2025073579_26022026_PF_FP_ABST
Abstract
Description
[0001] 2024PF30083 FC
[0002] AZIRIDINYL-FUNCTIONAL ORGANIC COMPOUNDS
[0003] FIELD OF THE INVENTION
[0004] The invention lies in the field of aziridinyl-functional organic compounds.
[0005] BACKGROUND
[0006] There is an increasing demand for coatings having enhanced ethanol resistance (abbreviated in the specification as ‘ER’), preferably combined with one or more of coating properties such as enhanced red wine resistance (abbreviated in the specification as ‘RWR’), and water resistance (abbreviated in the specification as ‘WR’).
[0007] Enhanced ER is desirable because it relates to the resistance of a coating towards ethanol which is a very particular aggressive organic solvent. However, enhancing the ER of a coating is a major challenge because ER relates to a coating performance which is such as to resist degradation when exposed to ethanol; coatings exhibiting enhanced ER are highly desirable and enhancing the ER of coatings is a challenging technical task. This challenge becomes more significant if one wishes to also combine enhanced ER with one or both of RWR and WR.
[0008] The WO 2021 / 148563 A1 provided for a multi-aziridine crosslinker composition characterized in that the multi-aziridine crosslinker composition is an aqueous dispersion having a pH ranging from 8 to 14 and comprises a multi-aziridine compound in dispersed form. The WO 2021 / 148563 A1 did not -at least- disclose aziridinyl-functional organic compounds as the latter is disclosed in the specification. The WO 2021 / 148563 A1 dealt with the provision of multi-aziridine crosslinkers which can be delivered and stored in water with a longer shelf life while maintaining sufficient reactivity towards carboxylic acid functional polymers (cf. WO 2021 / 148563 A1 , p. 2, II. 8-10). In addition, the WO 2021 / 148563 A1 did not disclose on how to improve the ER of coatings prepared from aziridinyl-functional organic compounds suitable as crosslinkers in coating compositions, let alone on how an improved ER would be combined with one or both of RWR and WR.
[0009] Therefore, there is a desire for coatings having enhanced ER preferably combined with one or both of RWR and WR, and thus, a technical solution to this challenge is required.
[0010] Such a desired technical solution still represents an unmet need since the solution to such a problem, is particularly challenging and complex. 2024PF30083 FC
[0011] The discussion of documents, acts, materials, devices, articles and the like are included in this specification solely for the purpose of providing a context for the present invention. It is not suggested or represented that any or all these matters formed part of the prior art base or were common general knowledge in the field relevant to the present invention as it existed before the priority date of the present invention.
[0012] SUMMARY OF THE INVENTION
[0013] The invention relates to an aziridinyl-functional organic component. The invention further relates to particles comprising an aziridinyl-functional organic component. The invention further relates to a composition comprising the aziridinyl- functional organic compound of the invention and / or the particles of the invention, and another ingredient. The invention further relates to a kit-of-parts, a cured form of the aziridinyl-functional organic component of the invention, a cured form of the particles of the invention, a cured form of a composition of the invention, and an article.
[0014] The goal of the invention is to provide for coatings having enhanced ethanol resistance, preferably combined with one or both of coating properties such as enhanced red wine resistance and water resistance.
[0015] This goal was surprisingly achieved by the aziridinyl-functional organic component, as described in the specification.
[0016] More particularly, it has surprisingly been found that when the aziridinyl-functional organic component of the invention was used in coating compositions, the coatings derived from said compositions had enhanced ethanol resistance combined with one or both of enhanced red wine resistance and enhanced water resistance.
[0017] The aziridinyl-functional organic component of the invention constitutes a major technological advancement for the paints and coatings industries since the coatings derived from coating compositions containing the aziridinyl-functional organic component of the invention had enhanced ethanol resistance preferably combined with one or both of enhanced red wine resistance and enhanced water resistance when compared with comparable coatings derived from the state-of-the-art. 2024PF30083 FC
[0018] BRIEF DESCRIPTION OF THE FIGURES
[0019] The specification contains 21 figures (Figures 1 to 21).
[0020] Figure 1 contains specific examples of aziridinyl-functional organic compounds of Formulae 1 to 13 (Formulae 1 to 13 - Figure 1), wherein n is an integer ranging from and including 1 up to and including 100, preferably n from and including 1 up to and including 80, more preferably n ranges from and including 1 up to and including 50, even more preferably n ranges from and including 1 up to and including 30, most preferably n ranges from and including 3 up to and including 80, especially n ranges from and including 3 up to and including 50, most especially n ranges from and including 3 up to and including 30; and wherein m is an integer ranging from and including 1 up to and including 100, preferably m ranges from and including 1 up to and including 40, more preferably m ranges from and including 5 up to and including 40; and wherein n’ is an integer ranging from and including 1 up to and including 100, preferably n’ ranges from and including 1 up to and including 10.
[0021] Figure 2 contains the formulae of Inventive Example 1.
[0022] Figure 3 contains the formulae Comparative Example 1.
[0023] Figure 4 contains the formulae of Inventive Example 2. Figure 5 contains the formulae of Inventive Example 3. Figure 6 contains the formulae of Inventive Example 4. Figure 7 contains the formulae of Inventive Example 5. Figure 8 contains the formulae of Inventive Example 6. Figure 9 contains the formulae of Inventive Example 7. Figure 10 contains the formulae of Inventive Example 8. Figure 11 contains the formulae of Inventive Example 9. Figure 12 contains the formulae of Inventive Example 10. Figure 13 contains the formulae of Inventive Example 11. Figure 14 contains the formulae of Inventive Example 12. Figure 15 contains the formulae of Inventive Example 13. Figure 16 contains the formulae of Inventive Example 14. Figure 17 contains the formulae of Inventive Example 15. Figure 18 contains the formulae of Inventive Example 16. Figure 19 contains the formulae of Inventive Example 17. Figure 20 contains the formulae Comparative Example 2. Figure 21 contains the formulae Comparative Example 3. 2024PF30083 FC
[0024] DETAILED DISCLOSURE OF THE INVENTION
[0025] The specification provides definitions for certain terms used in the specification. Any other term used in the specification that is not defined in the specification has the meaning attributed to it by one of ordinary skill in the art. As used herein, the term ‘specification’ includes also the claims.
[0026] In the specification, the term ‘enhanced ethanol resistance’ (or equally ‘enhanced ER’) of a coating means that the coating demonstrates a rating of at least 4, preferably a rating of 5, when the coating’s ER’s is tested as disclosed in the specification.
[0027] In the specification, the term ‘enhanced red wine resistance’ (or equally ‘enhanced RWR’) of a coating means that the coating demonstrates a rating of at least 4, preferably a rating of 5, when the coating’s RWR is tested as disclosed in the specification.
[0028] In the specification, the term ‘enhanced water resistance’ (or equally ‘enhanced WR’) of a coating means that the coating demonstrates a rating of at least 4, preferably a rating of 5, when the coating’s WR is tested as disclosed in the specification.
[0029] In the specification, the term ‘hydrocarbon’ means a chemical compound consisting of carbon and hydrogen only.
[0030] In the specification, the term ‘aliphatic hydrocarbon’ means that the hydrocarbon does neither contain any carbon-carbon triple bond (carbon-carbon triple bond unsaturation), nor any aromatic structure.
[0031] In the specification, the term ‘aliphatic hydrocarbyl’ means a univalent organic group formed by removing a hydrogen atom from an aliphatic hydrocarbon.
[0032] In the specification, the term ‘saturated aliphatic hydrocarbon’ means that the hydrocarbon does neither contain any cis- or trans-configured carbon-carbon double bond (carbon-carbon double bond unsaturation), nor any carbon-carbon triple bond (carbon-carbon triple bond unsaturation), nor any aromatic structure.
[0033] In the specification, the term ‘saturated aliphatic hydrocarbyl’ means a univalent organic group formed by removing a hydrogen atom from a saturated aliphatic hydrocarbon. Exemplary saturated aliphatic hydrocarbyls include but are not limited to methyl, ethyl, propyl.
[0034] In the specification, the term ‘saturated aliphatic hydrocarbylene’ means a bivalent organic group formed by removing two hydrogen atoms from a saturated aliphatic hydrocarbon, the free valences of which are not engaged in a double bond. Exemplary saturated aliphatic hydrocarbylenes include but are not limited to methylene. 2024PF30083 FC
[0035] In the specification, the term ‘curing’ or ‘cure’ means a process of becoming ‘set’ that is to form an irreversibly crosslinked network (the so-called ‘cured form’ or ‘cured composition’), a material that can no longer flow, be melted or dissolved. Herein, the terms ‘curing’ ‘cure’ and ‘crosslinking’ are used interchangeably; the curing may take place either at standard conditions (as these are defined in the specification), or by using heat, or by using pressure, or by applying vacuum, or by irradiation e.g. UV- radiation, or by any combination thereof.
[0036] In the specification, the term ‘room temperature’ means 23 ± 0.5 °C.
[0037] In the specification, the term ‘atmospheric pressure’ means a pressure of 1 atm (1 atm= 101325 Pa).
[0038] In the specification, the term ‘standard conditions’ means room temperature and atmospheric pressure, collectively.
[0039] In the specification, the term ‘lower than’ means that the relevant maximum boundary value is not included in the range.
[0040] In the specification, the term ‘higher than’ means that the relevant minimum boundary value is not included in the range.
[0041] In the specification, the term ‘molecular weight’ of a chemical compound means the sum of the atomic weight values of the atoms making up the molecule of said chemical compound.
[0042] In the specification, the term ‘comprising’ means that the list that immediately follows is non-exhaustive and may or may not include any other additional suitable items, for example, one or more additional feature(s), component(s) and / or substituent(s) as appropriate. The term ‘comprising’ is used interchangeably with the term ‘containing’.
[0043] In the specification, the term ‘consisting of’ means that the list that follows is exhaustive and does not include additional items. It is understood that the total sum of any quantities expressed in the specification as percentages cannot (allowing for rounding errors) exceed 100 %. However, where a list of components is non-exhaustive, the sum of the percentage for each of such components may be less than 100 % to allow a certain percentage for additional amount(s) of any additional component(s) that may not be explicitly described in the specification.
[0044] In the specification, the terms ‘effective’, ‘acceptable’, ‘active’ and / or ‘suitable’ (for example with reference to any process, use, method, application, preparation, product, material, formulation, compound, composition, monomer, oligomer, polymer precursor, and / or polymers of the present invention and / or described in the specification as appropriate) are understood to refer to those features of the invention which if used in the correct manner provide the required properties to that which they are 2024PF30083 FC added and / or incorporated to be of utility as described in the specification. Such utility may be direct for example where a material has the required properties for the aforementioned uses and / or indirect for example where a material has use as a synthetic intermediate and / or diagnostic tool in preparing other materials of direct utility. As used in the specification, these terms also denote that a functional group is compatible with producing effective, acceptable, active and / or suitable end products.
[0045] In the specification the term ‘article’ means an individual object or item or element of a class designed to serve a purpose or perform a particular function and can stand alone; the article can be in any size, form or shape. A substrate is an example of an article. Preferably, said article is selected from the group consisting of heatsensitive articles, non-heat sensitive articles and combinations thereof; more preferably said article is selected from the group of non-heat sensitive articles, even more preferably said article is selected from the group consisting of thermoplastic composite, thermoset composite, fibre reinforced composites, sandwich materials, e.g. sandwich materials comprising heat sensitive foam core, metal and combinations thereof. Typical examples of non-heat-sensitive articles include glass, ceramic, composite, fibre cement board, or metal, such as aluminium, copper or steel articles, such as carbon steel, where the main alloying constituent is carbon. Carbon steel usually contains carbon 0.2 and 1 .5 % w / w based on the total alloy composition and often contains other constituents such as manganese, chromium, nickel, molybdenum, copper, tungsten, cobalt, or silicon, depending on the desired steel properties. Steel has properties similar to iron if the amount of carbon is not too high, for example, not more than 1.5 % w / w based on the total alloy composition. The steel may be surface treated (treatment with zinc, or zinc phosphate or iron phosphate) or non-surface treated. Heat-sensitive articles, for example, heat-sensitive substrates, include plastic articles, wood articles for example solid wood, such as hardwood, softwood, plywood; veneer, particleboard, low-density fibreboard, medium-density fibreboard and high-density fibreboard, OSB (Oriented Strand Board) wood laminates, chipboard and other articles in which wood is an important constituent, such as foil covered wooden articles, engineered wood, plastic modified wood, plastic articles or wood plastic compounds (WPG); articles with cellulosic fibres, for example, cardboard or paper articles; textile and leather articles. Examples of plastic articles include unsaturated polyester resin-based compositions, ABS (acrylonitrile butadiene styrene), melamine-formaldehyde resins, polycarbonate, polyethylene, polypropylene, ethylene-propylene-diene monomer (EPDM), thermoplastic olefin (TPO), polyurethane (Pll), polypropylene oxide (PPO), polyethylene oxide (PEO), polyethylene terephthalate and nylon, for example, polyamide 6,6 and combinations thereof, for example, polycarbonate-ABS. Other heat-sensitive articles 2024PF30083 FC include objects that are a combination of a non-heat-sensitive part such as metal parts with a heat-sensitive part, such as any one of the aforementioned for example plastic hosing with heavy metal parts, strips for example aluminium frames with heat strips. The article can be a piece of domestic furniture, such as tables, chairs, cabinets, bedroom and bathroom furniture, office furniture, contract furniture such as school and child furniture, hospital furniture, restaurant and hotel furniture, kitchen cabinets and furniture, (flat) panels for interior design, interior and exterior windows and doors, interior and exterior window frames and door frames, exterior and interior sidings and flooring, articles for automotive applications, such as interior car parts, wheel covers, bumpers, under the hood parts, flexible flooring, sporting goods, cosmetics, audio-visual applications, such as TV sets, computer housing, phones, household appliances and satellite dishes.
[0046] The wavy lines shown in any one of the formulae shown in the specification signify what is well-known to one of ordinary skill in the art that the molecular structure beyond the point indicated by the wavy line, is not specified.
[0047] The decimal separator in numbers (also known as the radix character) is indicated with a period (‘.’).
[0048] Unless the context indicates otherwise, the plural forms of the terms in the specification are construed as including the singular form and vice versa.
[0049] For all upper and lower boundaries of any parameters given in the specification, the boundary value is included in each range for each parameter. All combinations of minimum and maximum values of the parameters described in the specification may be used to define the parameter ranges for various embodiments and preferences of the invention. In the context of the present invention unless stated to the contrary, the disclosure of alternative values for the upper or lower limit of the permitted range of a parameter, coupled with an indication that one of the said values is more highly preferred than the other, is to be construed as an implied statement that each intermediate value of the said parameter, lying in between the more preferred and the less preferred of said alternatives, is itself preferred to said less preferred value and also to each value lying between said less preferred value and said intermediate value.
[0050] Certain moieties, species, groups, repeat units, compounds, oligomers, polymers, materials, mixtures, compositions and / or formulations which comprise and / or are used in some or all of the invention as described in the specification may exist as one or more different forms such as any of those in the following non- exhaustive list: stereoisomers (such as enantiomers (e.g. S and / or R forms), diastereoisomers (e.g. E and / or Z forms), and / or geometric isomers); tautomers (e.g. 2024PF30083 FC keto and / or enol forms). The invention comprises and / or uses all such forms which are effective as defined in the specification.
[0051] The invention is as disclosed in the specification. This section (Detailed Disclosure of the Invention) provides for the detailed disclosure of the invention as well as for explicit preferments and embodiments of the claimed invention that are within the scope of the claimed invention. Many other variations, combinations and embodiments within the scope of the claims will be apparent to those skilled in the art.
[0052] The invention provides for aziridinyl-functional organic component (abbreviated as AZ-component) selected from the group consisting of i) to iii): i) aziridinyl- functional organic compounds of Formula A1 (abbreviated as AZ1 -compounds), ii) aziridinyl-functional organic compounds of Formula A2 (abbreviated as AZ2- compounds), and iii) mixtures thereof,
[0053] Formula A1 Formula A2 wherein each one of the AZ1 -compounds and AZ2-compounds has a molecular weight determined as the sum of the atomic weight values of the atoms making up the molecule of an AZ1 -compound or an AZ2-compound, of at least 600 and at most 10000, preferably at least 600 and at most 8000, more preferably at least 600 and at most 6000, most preferably at least 600 and at most 5000, especially at least 600 and at most 4000 for example 700 and at most 10000, for example at least 700 and at most 8000, for example at least 700 and at most 6000, for example at least 700 and at most 5000, for example at least 700 and at most 4000, for example at least 800 and at most 10000, for example at least 800 and at most 8000, for example at least 800 and at most 6000, for example at least 800 and at most 5000, for example at least 800 and at most 4000, for example at least 900 and at most 10000, for example at least 900 and at most 8000, for example at least 900 and at most 6000, for example at least 900 and at most 5000, for example at least 900 and at most 4000 for example at least 1000 and at most 10000, for example at least 1000 and at most 8000, for example at least 1000 and at most 6000, for example at least 1000 and at most 5000, for example at least 1000 and at most 4000 g / mol, 2024PF30083 FC and wherein each one of Xi and X2 consists of a linker and at least one group Z, as each one of the linker and the group Z is described in a) and b), respectively: a) the linker consists of carbon, hydrogen, oxygen, nitrogen and optionally sulfur atoms that are connected via covalent bonds amongst them, wherein the covalent bonds present in the linker are selected from the group consisting of carbon-carbon single bonds, carbon-hydrogen single bonds, carbon-oxygen single bonds, carbon-nitrogen single bonds, nitrogen-hydrogen single bonds, carbon-sulfur single bonds if sulfur atoms are present, carbon-nitrogen double bonds, carbon-oxygen double bonds, carboncarbon aromatic bonds, carbon-sulfur double bonds if sulfur atoms are present, and combination thereof; preferably the covalent bonds present in the linker are selected from the group consisting of carbon-carbon single bonds, carbon-hydrogen single bonds, carbon-oxygen single bonds, carbon-nitrogen single bonds, nitrogen-hydrogen single bonds, carbon-sulfur single bonds if sulfur atoms are present, carbon-nitrogen double bonds, carbon-oxygen double bonds, carbon-carbon aromatic bonds, carbon-sulfur double bonds if sulfur atoms are present, and combination thereof; more preferably the covalent bonds present in the linker are selected from the group consisting of carboncarbon single bonds, carbon-hydrogen single bonds, carbon-oxygen single bonds, carbon-nitrogen single bonds, nitrogen-hydrogen single bonds, carbon-sulfur single bonds if sulfur atoms are present, carbon-nitrogen double bonds, carbon-oxygen double bonds, and carbon-sulfur double bonds if sulfur atoms are present, and combinations thereof; and wherein the linker is covalently bonded to each one of the Y via a carbon-oxygen single bond as explained in the definition of Y, and wherein the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of groups of formula L1 (abbreviated as L1- groups), groups of formula L2 (abbreviated as L2-groups), groups of formula L3 (abbreviated as L3-groups), groups of formula L4 (abbreviated as L4-groups), groups of formula L5 (abbreviated as L5-groups), groups of formula L6 (abbreviated as L6-groups), groups of formula L7 (abbreviated as L7-groups), groups of formula L8 (abbreviated as L8-groups), groups of formula L9 (abbreviated as L9-groups), groups of formula L10 (abbreviated as L10-groups), groups of formula L11 (abbreviated as L11 -groups), groups of formula L12 (abbreviated as L12-groups), groups of formula L13 (abbreviated as L13- groups) only if sulfur atoms are present in the linker, and groups of formula L15 (abbreviated as L15-groups) only if sulfur atoms are present in the linker; preferably the oxygen atoms present in the linker participate in one or any combination of groups 2024PF30083 FC selected from the group consisting of L1 -groups, L2-groups, L7-groups, L10-groups, L11 -groups, L12-groups and L13-groups only if sulfur atoms are present in the linker; more preferably the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L10- groups, L11 -groups, L12-groups and L13-groups only if sulfur atoms are present in the linker; for example the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L11- groups, L12-groups and L13-groups only if sulfur atoms are present in the linker; for example the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L12-groups and L13- groups only if sulfur atoms are present in the linker; and wherein the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L3-groups, L4-groups, L5- groups, L6-groups, L7-groups, L8-groups, L9-groups, L13-groups only if sulfur atoms are present in the linker, L14-groups only if sulfur atoms are present in the linker, L15-groups only if sulfur atoms are present in the linker; preferably the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L7-groups, and L13-groups only if sulfur atoms are present in the linker; more preferably the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, and L13-groups only if sulfur atoms are present in the linker; and wherein if sulfur atoms are present in the linker, then the sulfur atoms present in the linker participate in one or any combination of groups of L13-groups, L14-groups and L15- groups; preferably if sulfur atoms are present in the linker, then the sulfur atoms present in the linker participate in L13-groups;
[0054] 2024PF30083 FC
[0055] Formula L4 Formula L5 Formula L6
[0056] Formula L10 Formula L11 Formula L12
[0057] Formula L13 Formula L14 Formula L15 and wherein each one of L1 -groups, L2-groups, L3-groups, L4-groups, L5-groups, L6-groups, L7- groups, L8-groups, L9-groups, L10-groups, L11 -groups, L12-groups, L13-groups, L14- groups and L15-groups, is connected to either a secondary or tertiary or quaternary carbon via every one of the attachment points shown in each one of the L1 -groups, L2- groups, L3-groups, L4-groups, L5-groups, L6-groups, L7-groups, L8-groups, L9-groups, L10-groups, L11-groups, L12-groups, L13-groups, L14-groups and L15-groups, and 2024PF30083 b) the group Z is of Formula 11
[0058] Formula 11 wherein n is an integer ranging from and including 1 up to and including 100, preferably n from and including 1 up to and including 80, more preferably n ranges from and including 1 up to and including 50, even more preferably n ranges from and including 1 up to and including 30, most preferably n ranges from and including 3 up to and including 80, especially n ranges from and including 3 up to and including 50, most especially n ranges from and including 3 up to and including 30; and
[0059] R’ is selected from the group consisting of hydrogen, methyl and C2-C4 saturated aliphatic hydrocarbyl, preferably R’ is selected from the group consisting of methyl and C2-C4 saturated aliphatic hydrocarbyl; and wherein the group Z is covalently connected to either a either a secondary or a tertiary, or a quaternary carbon atom of the linker, via a carbon-carbon single bond, or to an oxygen atom of the linker via a carbon-oxygen single bond wherein said oxygen atom of the linker belongs to any one of L6-groups, L10-groups, L11-groups, L12-groups, preferably said oxygen atom of the linker belongs to any one of L6-groups and L12-groups, more preferably said oxygen atom of the linker belongs to L12-groups, and wherein
[0060] Y is selected from the group consisting of groups of formula Y1 (abbreviated as Y1- groups) and groups of formula Y2 (abbreviated as Y2-groups),
[0061] Formula Y1
[0062] Formula Y2 2024PF30083 FC wherein
[0063] Ri is selected from the group consisting of hydrogen and methyl; and
[0064] R2 is selected from the group consisting of hydrogen, methyl, and C2-C5 saturated aliphatic hydrocarbyl; and
[0065] R3 is selected from the group consisting of hydrogen, methyl, and C2-C4 saturated aliphatic hydrocarbyl, preferably R3 is selected from the group consisting of methyl, and C2-C4 saturated aliphatic hydrocarbyl; and
[0066] R4 is selected from the group consisting of hydrogen, methyl, and C2-C4 saturated aliphatic hydrocarbyl;
[0067] Rs is selected from the group consisting of hydrogen, methyl, and C2-C18 saturated aliphatic hydrocarbyl, preferably Rs is selected from the group consisting of hydrogen and methyl, more preferably Rs is hydrogen;
[0068] R’s is a Cs-Cs saturated aliphatic hydrocarbylene;
[0069] Rs selected from the group consisting of hydrogen, methyl, and C2-C18 aliphatic hydrocarbyl, preferably is selected from the group consisting of hydrogen, methyl, and C2-C18 saturated aliphatic hydrocarbyl;
[0070] R? is selected from the group consisting of hydrogen, methyl, C2-C18 saturated aliphatic hydrocarbyl, CH2-O-(C=O)-Rs, CH2-O-R9, and CH2-(0-CRioHCRioH)p-ORn, wherein p is an integer ranging from and including 1 up to and including 35, Rs is a C1-C18 saturated aliphatic hydrocarbyl, R9 is selected from the group consisting of methyl, C2-C18 saturated aliphatic hydrocarbyl, Rwis independently selected from the group consisting of hydrogen, methyl, ethyl, Rn is selected from the group consisting of methyl, C2-C4 saturated aliphatic hydrocarbyl; preferably R7 is selected from the group consisting of methyl, C2-C18 saturated aliphatic hydrocarbyl, CH2-O-(C=O)-Rs, CH2-O-R9, and CH2-(O- CRioHCRioH)p-ORii, wherein p is an integer ranging from and including 1 up to and including 35, Rs is a C1-C18 saturated aliphatic hydrocarbyl, R9 is selected from the group consisting of methyl, C2-C18 saturated aliphatic hydrocarbyl, Rwis independently selected from the group consisting of hydrogen, methyl, ethyl, Rn is selected from the group consisting of methyl, C2-C4 saturated aliphatic hydrocarbyl; more preferably R7 is selected from the group consisting of C2-C18 saturated aliphatic hydrocarbyl, CH2-O- (C=O)-Rs, CH2-O-R9, and CH2-(0-CRioHCRioH)p-ORn, wherein p is an integer ranging from and including 1 up to and including 35, Rs is a C1-C18 saturated aliphatic hydrocarbyl, R9 is selected from the group consisting of methyl, C2-C18 saturated aliphatic hydrocarbyl, Rwis independently selected from the group consisting of hydrogen, methyl, ethyl, Rn is selected from the group consisting of methyl, C2-C4 saturated aliphatic hydrocarbyl; and wherein 2024PF30083 FC each one of the Y of the AZ1 -compounds and AZ2-compounds is covalently bonded to the oxygen of a L1 -group via a carbon-oxygen single bond, and wherein the Y in each of the AZ1 -compounds and AZ2-compounds may be the same or different to each other, preferably the Y in each one of the AZ1 -compounds and AZ2-compounds is the same.
[0071] The subject matter of this paragraph is mentioned in the specification as ‘AT.
[0072] Preferably the aziridinyl-functional organic component is as disclosed in A1 or as in any combination derived from the disclosure in this section and the entire specification, wherein the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L7- groups, L10-groups, L11 -groups, L12-groups and L13-groups only if sulfur atoms are present in the linker, and wherein the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L7-groups, L10-groups, L11 -groups, L12-groups and L13-groups only if sulfur atoms are present in the linker and wherein if sulfur atoms are present in the linker, then the sulfur atoms present in the linker participate in L13-groups.
[0073] The subject matter of this paragraph is mentioned in the specification as ‘A2’.
[0074] Preferably the aziridinyl-functional organic component is as disclosed in A1 or as in any combination derived from the disclosure in this and the entire specification, wherein the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L10- groups, L11-groups, and L12-groups, and wherein the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L10-groups, L11 -groups, and L12-groups, and wherein no sulfur atoms are present in the linker.
[0075] The subject matter of this paragraph is mentioned in the specification as ‘A3’. 2024PF30083 FC
[0076] Preferably the aziridinyl-functional organic component is as disclosed in A1 or as in any combination derived from the disclosure in this and the entire specification, wherein the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L11- groups, and L12-groups, and wherein the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L11 -groups, and L12- g roups, and wherein no sulfur atoms are present in the linker. The subject matter of this paragraph is mentioned in the specification as ‘A4’.
[0077] Preferably the aziridinyl-functional organic component is as disclosed in A1 or as in any combination derived from the disclosure in this and the entire specification, wherein the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups and L12-groups, and wherein the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, and L12-groups, and wherein no sulfur atoms are present in the linker.
[0078] The subject matter of this paragraph is mentioned in the specification as ‘A5’.
[0079] Preferably the aziridinyl-functional organic component is as disclosed in A1 or as in any combination derived from the disclosure in this and the entire specification, wherein the aziridinyl-functional organic component is selected from the group consisting of compounds of Formulae 1 to 13 (Formulae 1 to 13 - Figure 1), and mixtures thereof, wherein n is an integer ranging from and including 1 up to and including 100, preferably n from and including 1 up to and including 80, more preferably n ranges from and including 1 up to and including 50, even more preferably n ranges from and including 1 up to and including 30, most preferably n ranges from and including 3 up to and including 80, especially n ranges from and including 3 up to and including 50, most especially n ranges from and including 3 up to and including 30; and wherein m is an integer ranging from and including 1 up to and including 100, preferably m ranges from and including 1 up to and including 40, more preferably m ranges from and including 5 up to and including 40; and wherein n’ is an integer ranging from and including 1 up to 2024PF30083 FC and including 100, preferably n’ ranges from and including 1 up to and including 10. The subject matter of this paragraph is mentioned in the specification as ‘A6’.
[0080] The AZ-component can be prepared as follows: i) at room temperature and under inert atmosphere, mixing in an organic aprotic solvent -preferably a volatile polar aprotic solvent- a catalyst, at least one or more diisocyanates, at least one or more difunctional polyols and, optionally either at least one or more triisocyanates, or at least one or more trifunctional polyols (typically an AZ1- compound is prepared by using one or more diisocyanates and one or more difunctional polyols, while an AZ2-compound is typically prepared by using at least one or more diisocyanates, at least one or more difunctional polyols and, either at least one or more triisocyanates, or at least one or more trifunctional polyols); ii) subsequently, one or any combination of a diisocyanate comprising a Z-group, a diol comprising a Z-group, a diamine comprisining a Z-group and a monoamino-monoalcohol comprising a Z-group, is / are added to the mixture of step i) [the following compounds I to V) are exemplary compounds comprising a Z-group used in step ii]] 2024PF30083 FC wherein n is an integer ranging from and including 1 up to and including 100, preferably n from and including 1 up to and including 80, more preferably n ranges from and including 1 up to and including 50, even more preferably n ranges from and including 1 up to and including 30, most preferably n ranges from and including 3 up to and including 80, especially n ranges from and including 3 up to and including 50, most especially n ranges from and including 3 up to and including 30, and wherein n’ is an integer ranging from and including 1 up to and including 100, preferably n’ ranges from and including 1 up to and including 10; iii) subsequently heating the thus prepared mixture of step ii) at a temperature in the range of 50 to 90 °C; iv) subsequently, an (aziridinyl hydroxy)-functional organic compound (abbreviated in the specification as AZIROH) selected from the group consisting of (aziridinyl hydroxy)-functional organic compounds of formula K1 (abbreviated in the specification as AZIROH-L1), (aziridinyl hydroxy)-functional organic compounds of formula K2 (abbreviated in the specification as AZIROH-L2) and mixtures thereof, is dosed to the mixture of step iv) by maintaining the temperature in the range between 50 to 90 °C,
[0081] Formula K1 2024PF30083 FC
[0082] Formula K2 wherein
[0083] Ri is selected from the group consisting of hydrogen and methyl; and
[0084] R2 is selected from the group consisting of hydrogen, methyl, and C2-C5 saturated aliphatic hydrocarbyl; and
[0085] R3 is selected from the group consisting of hydrogen, methyl, and C2-C4 saturated aliphatic hydrocarbyl, preferably R3 is selected from the group consisting of methyl, and C2-C4 saturated aliphatic hydrocarbyl; and
[0086] R4 is selected from the group consisting of hydrogen, methyl, and C2-C4 saturated aliphatic hydrocarbyl;
[0087] Rs is selected from the group consisting of hydrogen, methyl, and C2-C18 saturated aliphatic hydrocarbyl, preferably Rs is selected from the group consisting of hydrogen and methyl, more preferably Rs is hydrogen;
[0088] R’s is a Cs-Cs saturated aliphatic hydrocarbylene;
[0089] Rs selected from the group consisting of hydrogen, methyl, and C2-C18 aliphatic hydrocarbyl, preferably is selected from the group consisting of hydrogen, methyl, and C2-C18 saturated aliphatic hydrocarbyl;
[0090] R? is selected from the group consisting of hydrogen, methyl, C2-C18 saturated aliphatic hydrocarbyl, CH2-O-(C=O)-Rs, CH2-O-R9, and CH2-(0-CRioHCRioH)p-ORn, wherein p is an integer ranging from and including 1 up to and including 35, Rs is a C1-C18 saturated aliphatic hydrocarbyl, R9 is selected from the group consisting of methyl, C2-C18 saturated aliphatic hydrocarbyl, Rwis independently selected from the group consisting of hydrogen, methyl, ethyl, Rn is selected from the group consisting of methyl, C2-C4 saturated aliphatic hydrocarbyl; preferably R7 is selected from the group consisting of methyl, C2-C18 saturated aliphatic hydrocarbyl, CH2-O-(C=O)-Rs, CH2-O-R9, and CH2-(O- CRioHCRioH)p-ORii, wherein p is an integer ranging from and including 1 up to and including 35, Rs is a C1-C18 saturated aliphatic hydrocarbyl, R9 is selected from the group consisting of methyl, C2-C18 saturated aliphatic hydrocarbyl, Rwis independently selected from the group consisting of hydrogen, methyl, ethyl, Rn is selected from the group consisting of methyl, C2-C4 saturated aliphatic hydrocarbyl; more preferably R7 is selected from the group consisting of C2-C18 saturated aliphatic hydrocarbyl, CH2-O- (C=O)-Rs, CH2-O-R9, and CH2-(0-CRioHCRioH)p-ORn, wherein p is an integer ranging 2024PF30083 FC from and including 1 up to and including 35, Rs is a C1-C18 saturated aliphatic hydrocarbyl, R9 is selected from the group consisting of methyl, C2-C18 saturated aliphatic hydrocarbyl, Rwis independently selected from the group consisting of hydrogen, methyl, ethyl, Rn is selected from the group consisting of methyl, C2-C4 saturated aliphatic hydrocarbyl; v) maintaining the temperature in the range of 30 to 90 °C and the reaction was continued at a temperature in the range of 30 to 90 °C, up until the all hydroxyl groups were consumed (the consumption of isocyanate groups was being monitored via FT-IR spectroscopy by absorption at about 2260 cm-1). If an aqueous dispersion of a AZ- component is desired, then water may be further added at a temperature between 10- 50 °C optionally followed by the removal of the organic aprotic solvent under vacuum. Optionally, the pH of dispersion might be raised to at least pH 7.5 and at most pH 14 with either an alkali hydroxide and / or an organic base, such as but not limited to triethylamine or ammonia.
[0091] Examples of organic polar aprotic solvents include but are not limited to 2-methoxypropyl acetate, N-methyl-2-pyrrolidone, N-butyl-2-pyrrolidone, dimethyl formamide, butyl acetate. Examples of volatile polar aprotic solvents include but are not limited to acetone, methyl ethyl ketone. Examples of catalysts include but are not limited to tin-based catalysts such as dibutyltin dilaurate, bismuth-based catalysts e.g. bismuth(lll) neodecanoate, manganese-based catalysts, zirconia-based catalysts, and 1 ,4-diazabicyclo[2,2,2]octane.
[0092] Diisocyanates are monomeric or polymeric organic compounds having an average of at most two isocyanate groups per molecule. Exemplary diisocyanates include aliphatic diisocyanates, aromatic diisocyanates and diisocyanates comprising a heteroatom selected from the group consisting of oxygen, nitrogen, sulfur, and combinations thereof, and wherein the heteroatom does not belong to an isocyanate group, and mixtures thereof. Exemplary diisocyanates (and particularly preferred) include but are not limited to tetramethylene diisocyanate, methylpentamethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, dodecamethylene diisocyanate, 1 ,4-diisocyanatocyclohexane, 1-isocyanato-3,3,5- trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate; IPDI), 4,4'- diisocyanatodicyclohexylmethane, 4,4'-diisocyanato-2,2-dicyclohexylpropane, 1 ,4- diisocyanatobenzene, 2,4-diisocyanatotoluene, 2,6-diisocyanatotoluene, 4,4'- diisocyanatodiphenylmethane, 2,2'- and 2,4'-diisocyanatodiphenylmethane, tetramethylxylylene diisocyanate, p-xylylene diisocyanate, p-isopropylidene diisocyanate, diisocyanates having a uretdione moiety, diisocyanates having an isocyanurate moiety, diisocyanates having a urethane moiety, diisocyanates having an 2024PF30083 FC allophanate moiety, diisocyanates having a biuret moiety, diisocyanates having a iminooxadiazinedione moiety, diisocyanates having a oxadiazinetrione moiety, diisocyanates having uretdione moieties diisocyanates having isocyanurate moieties, and mixtures thereof. Exemplary commercially available diisocyanates include but are not limited to Desmodur® W, Desmodur® N 3400 and Desmodur® N 3500, supplied by Covestro AG.
[0093] T riisocyanates are monomeric or polymeric organic compounds having three isocyanate groups per molecule. Exemplary commercially available triisocyanates include but are not limited to Desmodur® N 3200, Desmodur® ultra N 3300, Desmodur® ultra N 3600 and Desmodur® ultra N 3900, supplied by Covestro AG.
[0094] Difunctional polyols are monomeric or polymeric compounds having two hydroxyl groups per molecule having a molecular weight in the range of 50 to 5000, preferably 50 to 4000, for example 50 to 3000, for example 50 to 2000, for example 50 to 1000, for example 100 to 5000, for example 100 to 4000, for example 100 to 3000, for example 100 to 2000, for example 100 to 1000, for example 200 to 5000, for example 200 to 4000, for example 200 to 3000, for example 200 to 2000, for example 200 to 1000, for example 300 to 5000, for example 300 to 4000, for example 300 to 3000, for example 300 to 2000, for example 300 to 1000, for example 400 to 5000, for example 400 to 4000, for example 400 to 3000, for example 400 to 2000, for example 400 to 1000 g / mol. Difunctional polyols are available with a wide range of backbones. The most significant polyol backbones include but are not limited to ether, ester, carbonate, acrylic, methacrylic, urethane, caprolactone, and combinations thereof, e.g. ether-ester, estercarbonate, ether-carbonate, ether-ester-carbonate. Exemplary difunctional polyols include but are not limited to polyether difunctional polyols, polyester difunctional polyols, poly(ether-ester) difunctional polyols, polycarbonate difunctional polyols, poly(ether- carbonate) difunctional polyols, poly(ester-carbonate) difunctional polyols, poly(ether- ester-carbonate) difunctional polyols, polyacrylate difunctional polyols, polyurethane difunctional polyols, poly(carbonate-caprolactone) difunctional polyols. Poly tetrahydrofuran, polypropyleneglycol, poly(1 ,6-hexamethylene adipate), 1 ,6-hexanediol polycarbonate diol, and polycaprolactone, are some specific examples of difunctional polyols.
[0095] Trifunctional polyols are monomeric or polymeric compounds having three hydroxyl groups per molecule having a molecular weight in the range of 50 to 5000, preferably 50 to 4000, for example 50 to 3000, for example 50 to 2000, for example 50 to 1000, for example 100 to 5000, for example 100 to 4000, for example 100 to 3000, for example 100 to 2000, for example 100 to 1000, for example 200 to 5000, for example 200 to 4000, for example 200 to 3000, for example 200 to 2000, for example 200 to 1000, 2024PF30083 FC for example 300 to 5000, for example 300 to 4000, for example 300 to 3000, for example 300 to 2000, for example 300 to 1000, for example 400 to 5000, for example 400 to 4000, for example 400 to 3000, for example 400 to 2000, for example 400 to 1000 g / mol. Exemplary trifunctional polyols include but are not limited to glycerol, trimethylolpropane, ethoxylated trimethylolpropane, propoxylated trimethylolpropane, propoxylated glycerol.
[0096] The AZIROH can be prepared by reacting an aziridine compound of formula P1 (abbreviated in the specification as A-P1)
[0097] Formula P1 wherein
[0098] Ri is selected from the group consisting of hydrogen and methyl; and
[0099] R2 is selected from the group consisting of hydrogen, methyl, and C2-C5 saturated aliphatic hydrocarbyl; and
[0100] R3 is selected from the group consisting of hydrogen, methyl, and C2-C4 saturated aliphatic hydrocarbyl, preferably R3 is selected from the group consisting of methyl, and C2-C4 saturated aliphatic hydrocarbyl; and
[0101] R4 is selected from the group consisting of hydrogen, methyl, and C2-C4 saturated aliphatic hydrocarbyl. with one or more monoepoxides at a temperature in the range of 70 to 80 °C for about 20- 24 h under inert atmosphere, e.g. nitrogen, helium. This reaction (the terms refers to and encompasses any and all of the reactions mentioned just above in this section) takes places at any temperature from 20 to 110 °C, more preferably from 50 to 95 °C, and most preferably from 70 to 90 °C and its progress can be monitored via1H-NMR spectroscopy, and it is carried out till all epoxy groups are consumed; this is monitored and verified by1H-NMR spectroscopy where the characteristic1H-NMR chemical shift of the epoxy protons (2.5 - 3.0 ppm) is disappeared; preferably this reaction is carried out without solvent; however, if desired (for instance to reduce the viscosity), one or more organic solvents, e.g. toluene, 2-methyl-tetrahydrofurane can be used during or after the reaction. If a solvent is used, it is often convenient to first dissolve the monoepoxide in the solvent (or mixture of solvents) before adding the A-P1 to the reaction mixture. The molar ratio of the mol of the aziridine groups of the A-P1 to the mol of the epoxy group of the monoepoxide is at least 1 and at most 8, more preferably at least 1 and at most 4, 2024PF30083 FC even more preferably at least 1.1 and at most 3 and most preferably at least 1.2 and at most 2.2. Once the reaction is completed, the residual A-P1 is distilled off, preferably at a temperature from 60 to 90 °C, more preferably from 65 to 80 °C, and at reduced pressure, for example from 20 to 50 mbar (1 bar= 100000 Pa; 1 mbar= 100 Pa), preferably from 30-45 mbar. Preferably once the reaction is completed, the residual A- P1 is distilled off at reduced pressure from 20 to 50 mbar at 70 °C, more preferably from 30 to 45 mbar at 70 °C. Subsequently, a further distillation step for the removal of any unreacted A-P1 and any other volatiles is carried out at 25 to 40 °C at 2 to 4 mbar, until no A-P1 could be detected by1H-NMR spectroscopy. It is often useful to add an additional solvent to the reaction mixture prior to or during distillation, to facilitate the removal of the excess of A-P1. If desired, a base can be used during the reaction, to reduce possible sources of acid. Bases include both organic bases, like tertiary amines or inorganic bases like sodium or potassium carbonate or for instance calcium hydroxide. The inorganic bases can be filtered off after the reaction is completed.
[0102] Examples of A-P1 include but are not limited to propylene imine, 1 ,2- dimethyl aziridine, 2,2-dimethyl aziridine, 2-ethyl aziridine, butyl aziridine.
[0103] Monoepoxides are monomeric or polymeric organic compounds having an average of at most one epoxy group per molecule having a molecular weight in the range of 50 to 1000, preferably 50-500 g / mol. Examples of monoepoxides include but are not limited to ethylene oxide, propylene oxide, 2-ethyl oxirane, n-butyl glycidylether, 2-ethylhexylglycidylether, phenyl glycidyl ether, 4-tert-butylphenyl 2,3- epoxypropyl ether, allyl glycidyl ether, cyclohexene oxide cresol glycidyl ether (ortho or para) and glycidyl neodecanoate, lauryl alcohol ethoxylated glycidylether, 2,2- dimethyloxirane, 2-methyl-2-vinylepoxide, 1 -methylcyclopentene oxide, 1-oxaspiro[2.4] heptane, 2-methyl-1 ,2-epoxybutane, 2,2,3-trimethyloxirane, 2-methyl-2-(2-propen-2- yl)oxirane.
[0104] In an embodiment of the invention, there are provided particles comprising an aziridinyl-functional organic component (AZ-component) as the latter is defined in any one of A1 to A6 or as in any combination derived from the disclosure in this and the entire specification. The subject matter of this paragraph is mentioned in the specification as ‘A7’.
[0105] Preferably the particles as disclosed in A7 or as in any combination derived from the disclosure in this and the entire specification, have a scatter intensitybased average hydrodynamic diameter (DH) determined via dynamic light scattering according to the description, of at least 2 and at most 3000, preferably at least 2 and at most 2500, more preferably at least 2 and at most 2000, even more preferably at least 2 and at most 1500, for example at least 2 and at most 1000, for example at least 2 and at 2024PF30083 most 900, for example at least 2 and at most 800, for example at least 2 and at most 600, for example at least 2 and at most 500, for example at least 2 and at most 400, for example at least 2 and at most 350, for example at least 2 and at most 300, for example at least 10 and at most 3000, for example at least 10 and at most 2500, for example at least 10 and at most 2000, for example at least 10 and at most 1500, for example at least
[0106] 10 and at most 1000, for example at least 10 and at most 900, for example at least 10 and at most 800, for example at least 10 and at most 600, for example at least 10 and at most 500, for example at least 10 and at most 400, for example at least 10 and at most 350, for example at least 10 and at most 300, for example at least 20 and at most 3000, for example at least 20 and at most 2500, for example at least 20 and at most 2000, for example at least 20 and at most 1500, for example at least 20 and at most 1000, for example at least 20 and at most 900, for example at least 20 and at most 800, for example at least 20 and at most 600, for example at least 20 and at most 500, for example at least 20 and at most 400, for example at least 20 and at most 350, for example at least 20 and at most 300, for example at least 30 and at most 3000, for example at least 30 and at most 2500, for example at least 30 and at most 2000, for example at least 30 and at most 1500, for example at least 30 and at most 1000, for example at least 30 and at most 900, for example at least 30 and at most 800, for example at least 30 and at most 600, for example at least 30 and at most 500, for example at least 30 and at most 400, for example at least 30 and at most 350, for example at least 30 and at most 300, for example at least 40 and at most 3000, for example at least 40 and at most 2500, for example at least 40 and at most 2000, for example at least 40 and at most 1500, for example at least 40 and at most 1000, for example at least 40 and at most 900, for example at least 40 and at most 800, for example at least 40 and at most 600, for example at least 40 and at most 500, for example at least 40 and at most 400, for example at least 40 and at most 350, for example at least 40 and at most 300, for example at least 50 and at most 3000, for example at least 50 and at most 2500, for example at least 50 and at most 2000, for example at least 50 and at most 1500, for example at least 50 and at most 1000, for example at least 50 and at most 900, for example at least 50 and at most 800, for example at least 50 and at most 600, for example at least 50 and at most 500, for example at least 50 and at most 400, for example at least 50 and at most 350, for example at least 50 and at most 300, for example at least 60 and at most 3000, for example at least 60 and at most 2500, for example at least 60 and at most 2000, for example at least 60 and at most 1500, for example at least 60 and at most 1000, for example at least 60 and at most 900, for example at least 60 and at most 800, for example at least 60 and at most 600, for example at least 60 and at most 500, for 2024PF30083 FC example at least 60 and at most 400, for example at least 60 and at most 350, for example at least 60 and at most 300, for example at least 70 and at most 3000, for example at least 70 and at most 2500, for example at least 70 and at most 2000, for example at least 70 and at most 1500, for example at least 70 and at most 1000, for example at least 70 and at most 900, for example at least 70 and at most 800, for example at least 70 and at most 600, for example at least 70 and at most 500, for example at least 70 and at most 400, for example at least 70 and at most 350, for example at least 70 and at most 300, for example at least 80 and at most 3000, for example at least 80 and at most 2500, for example at least 80 and at most 2000, for example at least 80 and at most 1500, for example at least 80 and at most 1000, for example at least 80 and at most 900, for example at least 80 and at most 800, for example at least 80 and at most 600, for example at least 80 and at most 500, for example at least 80 and at most 400, for example at least 80 and at most 350, for example at least 80 and at most 300, for example at least 90 and at most 3000, for example at least 90 and at most 2500, for example at least 90 and at most 2000, for example at least 90 and at most 1500, for example at least 90 and at most 1000, for example at least 90 and at most 900, for example at least 90 and at most 800, for example at least 90 and at most 600, for example at least 90 and at most 500, for example at least 90 and at most 400, for example at least 90 and at most 350, for example at least 90 and at most 300, for f sxample at least 100 and at most 3000, for example at least 100 and at most 2500, for example at least 100 and at most 2000, for example at least 100 and at most 1500, for example at least 100 and at most 1000, for example at least 100 and at most 900, for example at least 100 and at most 800, for example at least 100 and at most 600, for example at least 100 and at most 500, for example at least 100 and at most 400, for example at least 100 and at most 350, for example at least 100 and at most 300 nm; especially the particles have a scatter intensity-based average hydrodynamic diameter (DH) determined via dynamic light scattering according to the description, of at least 2 and at most 3000, preferably at least 10 and at most 2000, more preferably at least 30 and at most 1000, most preferably at least 40 and at most 1000, for example at least 50 and at most 1000, for example at least 40 and at most 800, for example at least 50 and at most 800, for example at least 50 and at most 600, for example at least 50 and at most 500, for example at least 70 and at most 1000, for example at least 70 and at most 800, for example at least 70 and at most 600, for example at least 70 and at most 500, for example at least 90 and at most 500 nm. The subject matter of this paragraph is mentioned in the specification as ‘A8’. 2024PF30083 FC
[0107] The particles of the invention may optionally further comprise other components, such as pigments and / or waxes, and / or processing additives, for example degassing agents -if the particles are used in powder coatings-, smoothness, appearance enhancing agents or (light) stabilizers. Suitable stabilizers include for example primary and / or secondary antioxidants and UV stabilizers, for example quinones, (sterically hindered) phenolic compounds, phosphonites, phosphites, thioethers and HALS (hindered amine light stabilizers). Examples of suitable degassing agents include cyclohexane dimethanol bisbenzoate, benzoin and benzoin derivatives such as for example those described in WO 2002 / 050194 A1.
[0108] The particles of the invention may be obtained by a process comprising the steps of: i) providing an aqueous dispersion of the invention; and ii) removing the water -and any organic solvent if present- from the aqueous dispersion, preferably by spray-drying or freeze-drying or distillation under vacuum to obtain the particles; and iii) collecting the particles, and iv) optionally further drying the particles; and v) optionally applying means, e.g. grinding, that transform the collected particles into any form that a solid material may exist at standard conditions.
[0109] The particles of the invention may be present in a waterborne composition such as an aqueous dispersion.
[0110] Preferably the particles of the invention are as disclosed in any of A7 to A8 or as in any combination derived from the disclosure in this and the entire specification, wherein the particles comprise an aziridinyl-functional organic component (AZ-component) as the latter is defined in any one of A1 to A6 or as in any combination derived from the disclosure in this and the entire specification , in an amount of at least 5 and at most 100, for example at least 10 and at most 90, for example at least 20 and at most 80, for example at least 30 and at most 70, for example at least 30 and at most 60, for example at least 30 and at most 50, for example at least 30 and at most 40 wt%; more preferably, the particles of the invention consists of an aziridinyl-functional organic component (AZ-component) as the latter is defined in any one of A1 to A6 or as in any combination derived from the disclosure in this and the entire specification. The subject matter of this paragraph is mentioned in the specification as ‘A9’.
[0111] In an embodiment of the invention, there is provided a composition comprising: i) an aziridinyl-functional organic component as the latter is defined in any one of A1 to A6 or as in any combination derived from the disclosure in this and the entire specification, and / or particles as the latter are defined in any one of A7 to A9 or as in any 2024PF30083 FC combination derived from the disclosure in this and the entire specification, and ii) at least one more ingredient other than the aziridinyl-functional organic component and the particles. The subject matter of this paragraph is mentioned in the specification as ‘A10’.
[0112] The composition of the invention may be solid, semi-solid or liquid e.g. solventborne, waterborne e.g. aqueous dispersion, at standard conditions.
[0113] The composition of the invention may be prepared by mixing: i) an aziridinyl-functional organic component of the invention and / or the particles of the invention, and ii) at least one more ingredient other than the aziridinyl-functional organic component and the particles.
[0114] The mixing of the components i) and ii) may be carried out in the presence of water and / or an organic solvent at standard conditions, to obtain a liquid mixture. Alternatively, the mixing may be carried out by direct mixing of the components i) and ii) at standard conditions.
[0115] The at least one more ingredient other than the aziridinyl-functional organic component and the particles can be any one of or any combination of polymers (as for example those disclosed in the specification), water, solvents (as for example organic solvents), waxes, wetting additives, dispersants, fillers, thickeners, antifoaming additives, devolatilizers, flow control additives, colorants (including pigments, effect pigments and dyes), preservatives, surfactants, slip additives, plasticizers, anti-freeze agents, neutralizers, biological material (such as inoculants), nutrients, micronutrients, surface additives, inert materials [such as graphite, carbide, carbonate, an oxide of carbon, a cyanide, silica, clays (e.g. talc), silicate minerals e.g. mica], flakes of a translucent polymeric film on an inert carrier, and stabilizers. Waxes are grouped as either natural or synthetic, with this classification being possible because of their origin. The natural ones are further categorized into animal, vegetable and mineral waxes (vegetable waxes are also known as plant waxes). Examples of synthetic waxes include but are not limited to paraffin wax, microcrystalline wax, polyolefin wax (e.g. polyethylene wax, polypropylene wax), polytetrafluoroethylene wax, Vestowax® waxes (offered by Evonik), Fischer-Tropsch waxes, polyamide wax and polyvinyl wax. Examples of animal waxes include but are not limited to beeswax, Chinese wax, lanolin, shellac wax (from the lac insect Kerria lacca), spermaceti (from the head cavities and blubber of the sperm whale). Examples of vegetable waxes include but are not limited to bayberry wax, candelilla wax, carnauba wax, esparto wax, ouricury wax, rice bran wax, soy wax, tallow tree wax, jojoba oil. Examples of mineral waxes include but are not limited to ceresin, montan wax, ozocerite, and peat wax. The type of wax in a composition of the invention can be identified via one or a combination of analytical techniques such as Nuclear 2024PF30083 FC
[0116] Magnetic Resonance (NMR), Fourier Transform Infrared spectroscopy (FT-IR) and Differential Scanning Calorimetry (DSC). A wetting and dispersing agent can aid in mixing inorganic particles in the composition of the invention. Suitable wetting and dispersing additives include ionic and non-ionic products and include solutions of organo- modified polyacrylates, polyacrylates, sodium polyacrylate, polyurethane, phosphoric acid ester, star polymers, and modified polyethers. Suitable thickeners include agar, carboxy methylcellulose, carrageen, chitin, fucoidan, ghatti, gum arabic, karaya, laminaran, locust bean gum, pectin, alginate, guar gum, xanthan gum, diutan gum, and tragacanth, bentonite clays, HELIR (hydrophobically modified, ethoxylated urethane) thickeners, HASE (hydrophobically modified, alkali-swellable emulsion) thickeners and polyacrylates. Gums are generally preferred because of their low cost, availability and superior ability to enhance the physical characteristics of the resultant film. Examples of colorants include dyes or pigmented dispersions. Examples of suitable dyes include: anthraquinone, triphenylmethane, phthalocyanine and derivatives thereof, and diazonium salts. Pigment dispersions can contain pigments such as pigment red 112 (CAS No. 6535-46-2), pigment red 2 (CAS No. 6041-94-7), pigment red 48:2 (CAS No. 7023-61-2), pigment blue 15:3 (CAS No. 147-14-8), pigment green 36 (CAS No. 14302- 13-7), pigment green 7 (CAS No. 1328-53-6), pigment yellow 74 (CAS No. 6358-31-2), pigment orange 5 (CAS No. 3468-63-1), pigment violet 23 (CAS No. 6358-30-1), pigment black 7 (CAS No. 97793-37-8), and pigment white 6 (CAS No. 98084-96-9). The colorant may be present in the composition of the invention in an amount of 0-50 wt% of the composition of the invention, preferably 1-10 wt % of the composition of the invention. Examples of suitable antifoaming additives include polyethylene glycol, glycerin, mineral oil defoamers, silicone defoamers, and non-silicone defoamers (such as polyethers, polyacrylates), dimethylpolysiloxanes (silicone oils), arylalkyd modified polysiloxanes, polyether siloxane copolymer containing fumed silica. The antifoaming additive may be present in the composition of the invention in an amount of 0-0.5 wt% of the composition of the invention. Examples of suitable effect pigments include aluminium, pearlescent pigment in different particle sizes. The effect pigments are commonly used to create a nice cosmetic look on the seeds. Suitable examples of flakes of a translucent polymeric film on an inert carrier (a carrier which has no detectable, harmful consequences for the environment, in particular for the seed or the outgrowing plant in the quantities present) for providing the seeds with a light-reflecting appearance, are described in WO 03 / 003812 A. Solvents may be selected from the group consisting of water, alcohols, and hydrocarbons. Also, mixtures of solvents can be used. It is preferred that the solvent is liquid at standard conditions. Examples of suitable solvents include glycols and their esters and ethers, in particular ethylene and propylene glycols and their esters and 2024PF30083 FC ethers, for instance, esters and ethers with Ci-Ce alkyl groups and / or aromatic groups, such as methyl, ethyl, propyl, butyl, benzyl and phenyl ethers, including mono ethers and dialkyl ethers, and esters of these ethers, such as acetates, and ethylene and propylene glycol esters, for instance of fatty acids; polyethylene glycol (PEG) and polypropylene glycol and esters thereof, especially with fatty acids; butyl cellosolve, butyl carbitol, polyethylene glycol; N-butylpyrrolidone, glycerin, alkyl alcohols with up to 10 carbon atoms, such as ethanol, propanol and butanol. Other examples of solvents include dipropylene glycol methyl ether and propylene glycol methyl ether. An important solvent is ethylene glycol. Further examples include propylene tetramer and synthetic ester oils such as lactate esters, particularly ethyl lactate and benzoate esters e.g. iso-propyl or 2- ethylhexyl benzoates. Aromatic hydrocarbons such as xylene, aliphatic and paraffinic solvents and vegetable oils can also be used as solvent, though are less preferred. Suitable surfactants include amphiphilic organic compounds, usually comprising a branched, linear or aromatic hydrocarbon, fluorocarbon or siloxane chain as tail and a hydrophilic group. Some types of surfactants include non-ionic, anionic, cationic and amphoteric surfactants, and organosilicone and organofluorine surfactants. Some examples of surfactants include polyoxyethylene glycol and polyoxypropylene ethers and esters, in particular alkyl, aryl and alkylaryl ethers thereof, and sulphates, phosphates and sulphonic acid compounds of such ethers, glucoside (alkyl) ethers, glycerol esters, such as alkyl and fatty acid esters, sorbitan (alkyl) esters, acetylene compounds, cocamide compounds, block copolymers of polyethylene glycol and propylene glycol. Further examples of surfactants include alkylamine salts and alkyl quaternary ammonium salts, for example betain type surfactants, amino acid type surfactants; and polyhedric alcohols, fatty acid esters, in particular C12-C18 fatty acids, for instance of polyglycerin, pentaerythritol, sorbitol, sorbitan, and sucrose, polyhydric alcohol alkyl ethers, fatty acid alkanol amides, and propoxylated and ethoxylated compounds such as fatty alcohol ethoxylates, polyethyxlated tallow amine and alkylphenol ethoxylates. Some examples of anionic surfactants include sulphates, sulphonic acid compounds and phosphates, for example lignin sulphonates and (linear) alkylaryl sulphonates. Suitable anti-freeze agents include ethylene glycol, propylene glycol, 1 ,3-butylene glycol, hexylene glycol, diethylene glycol, and glycerin, with the preferred glycols being ethylene glycol and propylene glycol. Stabilizers include but are not limited to primary and / or secondary antioxidants and UV stabilizers, for example quinones, (sterically hindered) phenolic compounds, phosphonites, phosphites, thioethers and HALS (hindered amine light stabilizers). 2024PF30083 FC
[0117] Preferably the composition is as disclosed in A10 or as in any combination derived from the disclosure in this and the entire specification, wherein the at least one more ingredient other than the aziridinyl-functional organic component and the particles, is a polymer; preferably, the polymer is selected from the group consisting of polyesters, polyamides, polycarbonates, polyimides, alkyds, uralkyds, polyacrylics, polyurethanes, poly(urethane-acrylic)s, and mixtures thereof, preferably the polymer is selected from the group consisting of polyamides, polyacrylics, polyurethanes, poly(urethane-acrylic)s, and mixtures thereof, most preferably the polymer is selected from the group consisting of polyacrylics, polyurethanes, poly(urethane-acrylic)s, and mixtures thereof, preferably the polymer is a carboxylic acid functional polymer; preferably, the carboxylic acid functional polymer is selected from the group consisting of carboxylic acid functional polyesters, carboxylic acid functional polyamides, carboxylic acid functional polycarbonates, carboxylic acid functional polyimides, carboxylic acid functional alkyds, carboxylic acid functional uralkyds, carboxylic acid functional polyacrylics, carboxylic acid functional polyurethanes, carboxylic acid functional poly(urethane-acrylic)s, and mixtures thereof, preferably the carboxylic acid functional polymer is selected from the group consisting of carboxylic acid functional polyamides, carboxylic acid functional polyacrylics, carboxylic acid functional polyurethanes, carboxylic acid functional poly(urethane-acrylic)s, and mixtures thereof, most preferably the carboxylic acid functional polymer is selected from the group consisting of carboxylic acid functional polyacrylics, carboxylic acid functional polyurethanes, carboxylic acid functional poly(urethane-acrylic)s, and mixtures thereof. In the specification, the term ‘polyacrylic’ means a polymer comprising reacted residues of acrylic acid and / or methacrylic acid and / or an ester of acrylic acid and / or an ester of methacrylic acid, and / or styrene, and / or acrylonitrile, and / or acrylamide, and / or esters of itaconic acid, and / or itaconic acid, and / or divinyl benzene, and / or methacrylonitrile, and / or vinyl esters and / or vinyl halides, and / or esters of fumaric acid, and / or fumaric acid; preferably the polyacrylic is any polymer consisting of reacted residues of acrylic acid and / or methacrylic acid and / or an ester of acrylic acid and / or an ester of methacrylic acid, and / or styrene, and / or acrylonitrile, and / or acrylamide, and / or esters of itaconic acid, and / or itaconic acid, and / or divinyl benzene, and / or methacrylonitrile, and / or vinyl esters and / or vinyl halides, and / or esters of fumaric acid, and / or fumaric acid. In the specification the term ‘carboxylic acid functional polymer’ means a polymer which has an acid value determined according to the ASTM D1639-90(1996)e1 of at least 5 and at most 300, preferably at least 8 and at most 200, more preferably at least 10, and at most 150 mg KOH / g and wherein the polymer may optionally comprise functional groups. Analogously, the term ‘carboxylic acid functional polyester’ means a polyester which has an acid value determined 2024PF30083 FC according to the ASTM D1639-90(1996)e1 of at least 5 and at most 300, preferably at least 8 and at most 200, more preferably at least 10, and at most 150 mg KOH / g and wherein the polyester may optionally comprise ionic functional groups. Analogously, the term ‘carboxylic acid functional polyamide’ means a polyamide which has an acid value determined according to the ASTM D1639-90(1996)e1 of at least 5 and at most 300, preferably at least 8 and at most 200, more preferably at least 10, and at most 150 mg KOH / g and wherein the polyamide may optionally comprise ionic functional groups. Analogously, the term ‘carboxylic acid functional polycarbonate’ means a polycarbonate which has an acid value determined according to the ASTM D1639-90(1996)e1 of at least 5 and at most 300, preferably at least 8 and at most 200, more preferably at least 10, and at most 150 mg KOH / g and wherein the polycarbonate may optionally comprise ionic functional groups. Analogously, the term ‘carboxylic acid functional polyimide’ means a polyimide which has an acid value determined according to the ASTM D1639- 90(1996)e1 of at least 5 and at most 300, preferably at least 8 and at most 200, more preferably at least 10, and at most 150 mg KOH / g and wherein the polyimide may optionally comprise ionic functional groups. Analogously, the term ‘carboxylic acid functional alkyd’ means an alkyd which has an acid value determined according to the ASTM D1639-90(1996)e1 of at least 5 and at most 300, preferably at least 8 and at most 200, more preferably at least 10, and at most 150 mg KOH / g and wherein the alkyd may optionally comprise ionic functional groups. Analogously, the term ‘carboxylic acid functional uralkyd’ means a uralkyd which has an acid value determined according to the ASTM D1639-90(1996)e1 of at least 5 and at most 300, preferably at least 8 and at most 200, more preferably at least 10, and at most 150 mg KOH / g and wherein the uralkyd may optionally comprise ionic functional groups. Analogously, the term ‘carboxylic acid functional polyacrylic’ means a polyacrylic which has an acid value determined according to the ASTM D1639-90(1996)e1 of at least 5 and at most 300, preferably at least 8 and at most 200, more preferably at least 10, and at most 150 mg KOH / g and wherein the polyacrylic may optionally comprise ionic functional groups. Analogously, the term ‘carboxylic acid functional polyurethane’ means a polyurethane which has an acid value determined according to the ASTM D1639-90(1996)e1 of at least 5 and at most 300, preferably at least 8 and at most 200, more preferably at least 10, and at most 150 mg KOH / g and wherein the polyurethane may optionally comprise ionic functional groups. Analogously, the term ‘carboxylic acid functional poly(urethane-acrylic)’ means a poly(urethane-acrylic) which has an acid value determined according to the ASTM D1639-90(1996)e1 of at least 5 and at most 300, preferably at least 8 and at most 200, more preferably at least 10, and at most 150 mg KOH / g and wherein the poly(urethane- 2024PF30083 FC acrylic) may optionally comprise ionic functional groups. The subject matter of this paragraph is mentioned in the specification as ‘A1 T.
[0118] Preferably the composition is as disclosed in A11 or as in any combination derived from the disclosure in this and the entire specification, wherein the polymer -as disclosed in A11-, is present in an amount of at least 5 and at most 65, preferably at least 10 and at most 60, more preferably at least 20, and at most 55, for example at least 30 and at most 50 wt% on the total weight of the composition, and wherein the total amount of all the components that make up the composition totals 100 wt%. The subject matter of this paragraph is mentioned in the specification as ‘A12’.
[0119] Preferably the composition is as disclosed in any one of A10 to A12 or as in any combination derived from the disclosure in this and the entire specification , wherein the at least one more ingredient other than the aziridinyl-functional organic component and the particles is water; preferably, the water is present in an amount of at least 30 and at most 95, preferably at least 45 and at most 85, for example at least 50, and at most 70, for example at least 55 and at most 65 wt% on the total weight of the composition, and wherein the total amount of all the components that make up the composition totals 100 wt%. The subject matter of this paragraph is mentioned in the specification as ‘A13’.
[0120] Preferably the composition is as disclosed in any one of A10 to A13 or as in any combination derived from the disclosure in this and the entire specification , wherein the composition is a waterborne composition, preferably an aqueous dispersion; preferably, the water in the waterborne composition (or in the aqueous dispersion) is present in an amount of at least 30 and at most 95, preferably at least 45 and at most 85, for example at least 50, and at most 70, for example at least 55 and at most 65 wt% on the total weight of the waterborne composition (or of the aqueous dispersion), and wherein the total amount of all the components that make up the waterborne composition (or the aqueous dispersion) totals 100 wt%. The subject matter of this paragraph is mentioned in the specification as ‘A14’.
[0121] Preferably the composition is as disclosed in any one of A10 to A14 or as in any combination derived from the disclosure in this and the entire specification , wherein the composition is a waterborne composition, preferably an aqueous dispersion and has a pH determined according to the ISO 976:2013, of at least 7.5 and at most 14.0, preferably at least 8.0 and at most 14.0, for example at least 8.5 and at most 13.5, for example at least 9.0 and at most 13.0, for example at least 9.2 and at most 12.5, for example at least 9.4 and at most 12.0, for example at least 9.6 and at most 11.6, for example at least 10.5, and at most 11.5. The subject matter of this paragraph is mentioned in the specification as ‘A15’. 2024PF30083 FC
[0122] Preferably the composition is as disclosed in any one of A10 to A15 or as in any combination derived from the disclosure in this and the entire specification , wherein the composition is a waterborne composition, preferably the composition is an aqueous dispersion further comprising an organic solvent in an amount of at most 40, preferably at most 30, for example at most 25, for example at most 20, for example at most 12, for example at most 10, for example at most 8, for example at most 5, for example at most 4, for example at most 3, for example at most 2, for example at most 1 , for example at most 0.5, for example at most 0.2, for example at most 0.1 wt% on the total weight of the waterborne composition (or the aqueous dispersion); more preferably, the waterborne composition (or the aqueous dispersion) is free of an organic solvent. The subject matter of this paragraph is mentioned in the specification as ‘A16’.
[0123] The waterborne composition (or the aqueous dispersion) of the invention may be obtained by a process comprising the steps of: a) mixing the AZ-component -as this is disclosed in the entire specification-, with an organic solvent to obtain a mixture A; and b) mixing either the AZ-component component -as this is disclosed in the entire specification-, or the mixture A, with a dispersant to obtain a mixture B; and c) mixing either water and a base, or basic aqueous medium with the mixture B to obtain a mixture C; and d) optionally, (though preferably), removing the organic solvent from the mixture C to obtain a mixture D, and optionally mixing either additional water or a basic aqueous medium into the mixture D, to obtain the aqueous dispersion of the AZ- component.
[0124] More particularly, the aqueous dispersion of the invention may be prepared by several ways. For example, one approach involves the preparation of the AZ-component in solvent and after purification (for instance by distilling off the excess of AZIROH), the AZ-component is being introduced into water wherein optionally surfactants / dispersants, surface tension modifiers, defoamers, solvents, thickeners and / or any other additives may also be present. The introduction of the AZ-component into the water can be done by using at least one surfactant (preferably at least one nonionic surfactant) and adding the AZ-component to water with good mixing. Usually, a high shear mixer is most suitable for this process to ensure thorough mixing. If desired and if present, the solvent can be partly or completely distilled off. It is preferred to use a base during this process to ensure good retention of the aziridine groups. Preferably, part or all of the base (intended to be used) is added to the AZ-component prior to dispersing into water. Preferably, a volatile organic base is added to the AZ-component, and an inorganic base is added to the water prior to the AZ-component is being 2024PF30083 FC introduced into the water. Alternatively, and often preferred, the water wherein optionally surfactants / dispersants, surface tension modifiers, defoamers, solvents, thickeners and / or any other additives may also be present, is slowly added to the AZ-component, and after phase inversion, the mixture is further diluted with water to obtain the aqueous dispersions of the invention. Preferably, the pH of the thus prepared aqueous compositions of the invention should be at least 7.5 and at most 14.0, preferably at least 8.0 and at most 14.0, for example at least 8.5 and at most 13.5, for example at least 9.0 and at most 13.0, for example at least 9.2 and at most 12.5, for example at least 9.4 and at most 12.0, for example at least 9.6 and at most 11. 6. In order to achieve that, it is preferred that the pH can be adjusted with base, preferably inorganic or organic base. The inventive aqueous dispersions preferably comprise one or any combination of ammonia, a secondary amine, tertiary amine, LiOH, NaOH and KOH to adjust the pH to the desired value. Preferred amines are ammonia, dimethyl ethanolamine, diisopropylamine, isopropanol amine, diethyl ethanolamine, N,N dimethyl isopropanol amine, 3-dimethylamino-1 -propanol, 2-[2-(dimethylamino)ethoxy] ethanol, N-ethyl morpholine and dimethyl benzylamine and triethylamine. Examples of a preparation of an aqueous dispersion of the invention is shown in the Examples.
[0125] The waterborne composition of the invention may be prepared by mixing the aqueous dispersions of the invention with aqueous dispersions of polymers. Preferably, this can be done by slowly adding and mixing an aqueous dispersion of the invention into an aqueous dispersion of a polymer. Alternatively, an aqueous dispersion of a polymer may be slowly added and mixed into an aqueous dispersion of the invention -for instance under high-shear-, or they may be mixed using an inline mixing device. Preferably, the aqueous dispersions of the invention comprise a surfactant (preferably a non-ionic surfactant) in order to facilitate and enable thorough mixing with the aqueous dispersion of the polymer. Preferably, the pH of the thus prepared aqueous compositions of the invention should be at least 7.5 and at most 14.0, preferably at least 8.0 and at most 14.0, for example at least 8.5 and at most 13.5, for example at least 9.0 and at most 13.0, for example at least 9.2 and at most 12.5, for example at least 9.4 and at most 12.0, for example at least 9.6 and at most 11. 6. In order to achieve that, it is preferred that the aqueous dispersions of the invention have a pH of at least 7.5 and at most 14.0, preferably at least 8.0 and at most 14.0, for example at least 8.5 and at most
[0126] 13.5, for example at least 9.0 and at most 13.0, for example at least 9.2 and at most
[0127] 12.5, for example at least 9.4 and at most 12.0, for example at least 9.6 and at most
[0128] 11.6, for example at least 10.5 and at most 11.5, and the aqueous dispersions of the polymers have a pH of at least 7.5 and at most 14.0, preferably at least 8.0 and at most 14.0, for example at least 8.5 and at most 13.5, for example at least 9.0 and at most 2024PF30083 FC
[0129] 13.0, for example at least 9.2 and at most 12.5, for example at least 9.4 and at most 12.0, for example at least 9.6 and at most 11. 6.
[0130] In an embodiment of the invention, there is provided a kit-of-parts comprising parts A and B which are physically separated from each other, wherein: i) the part A comprises one or any combination of an aziridinyl-functional organic component as disclosed in any one of A1 to A6 or as in any combination derived from the disclosure in this and the entire specification, particles as disclosed in any one of A7 to A9 or as in any combination derived from the disclosure in this and the entire specification, a composition as disclosed in any one of A10 to A16 or as in any combination derived from the disclosure in this and the entire specification , and ii) a polymer, wherein the part A does not comprise the polymer of the part B, and the part B does neither comprise the aziridinyl-functional organic component of part A, nor the particles of part A, nor the composition of part A. The subject matter of this paragraph is mentioned in the specification as ‘A17’.
[0131] Preferably, the kit-of-parts is as disclosed in A17 or as in any combination derived from the disclosure in this and the entire specification, wherein the polymer is selected from the group consisting of polyesters, polyamides, polycarbonates, polyimides, alkyds, uralkyds, polyacrylics, polyurethanes, poly(urethane-acrylic)s, and mixtures thereof, preferably the polymer is selected from the group consisting of polyamides, polyacrylics, polyurethanes, poly(urethane-acrylic)s, and mixtures thereof, most preferably the polymer is selected from the group consisting of polyacrylics, polyurethanes, poly(urethane-acrylic)s, and mixtures thereof, preferably the polymer is a carboxylic acid functional polymer; preferably, the carboxylic acid functional polymer is selected from the group consisting of carboxylic acid functional polyesters, carboxylic acid functional polyamides, carboxylic acid functional polycarbonates, carboxylic acid functional polyimides, carboxylic acid functional alkyds, carboxylic acid functional uralkyds, carboxylic acid functional polyacrylics, carboxylic acid functional polyurethanes, carboxylic acid functional poly(urethane-acrylic)s, and mixtures thereof, preferably the carboxylic acid functional polymer is selected from the group consisting of carboxylic acid functional polyamides, carboxylic acid functional polyacrylics, carboxylic acid functional polyurethanes, carboxylic acid functional poly(urethane-acrylic)s, and mixtures thereof, most preferably the carboxylic acid functional polymer is selected from the group consisting of carboxylic acid functional polyacrylics, carboxylic acid functional polyurethanes, carboxylic acid functional poly(urethane-acrylic)s, and mixtures thereof. The subject matter of this paragraph is mentioned in the specification as ‘A18’. 2024PF30083 FC
[0132] In an embodiment of the invention, there is provided a cured form of i) an aziridinyl-functional component as disclosed in any one of A1 to A6 or as in any combination derived from the disclosure in this and the entire specification, or ii) particles as disclosed in any one of A7 to A9 or as in any combination derived from the disclosure in this and the entire specification, or iii) a composition as disclosed in any one of 10 to 16 or as in any combination derived from the disclosure in this and the entire specification. The subject matter of this paragraph is mentioned in the specification as ‘A19’.
[0133] Preferably the cured form is as disclosed in A19 or as in any combination derived from the disclosure in this and the entire specification, wherein the cured form is selected from the group consisting of coatings, films and 3D-objects other than coatings and films, and combinations thereof. The subject matter of this paragraph is mentioned in the specification as ‘A20’.
[0134] Preferably, the cured form of the aziridinyl-functional component of the invention as the aziridinyl-functional component is disclosed in any one of A1 to A6 or as in any combination derived from the disclosure in this and the entire specification , is obtained upon chemical reaction (resulting in the formation of irreversible covalent chemical bonds) or a combination of physical drying and chemical reaction. The curing of the aziridinyl-functional component of the invention may take place either at standard conditions (as these are defined in the specification), or by using heat, or by using pressure, or by applying vacuum, or by irradiation, e.g. UV-radiation, or by any combination thereof. Preferably the aziridinyl-functional component of the invention are cured at a temperature of at least 0 and at most 85, preferably at least 15 and at most 80, more preferably at least 23 and at most 70, most preferably at least 30 and at most 85, for example at least 15 and at most 30 °C, for time periods that may vary and are preferably of at most 60, more preferably at most 30, even more preferably at most 15 min. Preferably the aziridinyl-functional component of the invention are cured in the presence of Lewis acids, metal salts or peptide coupling agents. Exemplary Lewis acid compounds include but are not limited to aluminium (III) chloride, boron trifluoride, trimethyl borane. Exemplary metal salts include but are not limited to titanium (IV) isopropoxide, zinc (II) carbonate, zinc (II) ammonium carbonate, zirkonium (IV) ammonium carbonate. Exemplary peptide coupling agents include but not limited to succinimides, benzatriazole, 1 :1 salt of 4-dimethylaminopyridine and para-toluene sulfonic acid. Obviously, curing at elevated temperatures and at atmospheric pressure requires shorter curing time; curing may also be affected by using pressure or by applying vacuum, or by irradiation, e.g. UV-radiation, or by any combination thereof. The subject matter of this paragraph is mentioned in the specification as ‘A2T. 2024PF30083 FC
[0135] Preferably, the cured form of the aziridinyl-functional component of the invention as the aziridinyl-functional component is disclosed in any one of A1 to A6 or as in any combination derived from the disclosure in this and the entire specification , is obtained upon curing the aziridinyl-functional component of the invention in the presence of a polymer -preferably a carboxylic acid functional polymer- at standard conditions for example 12-48 h (preferably 24-48 h), and / or by heat-curing at elevated temperatures and at atmospheric pressure for example 70-80 °C for 10-60 min (preferably 15-30 min, more preferably 20 min), and / or any combination of curing at room temperature and curing at elevated temperatures; annealing steps (e.g. 50°C for 16 h) may also be included especially in between curing at elevated temperatures and at atmospheric pressure and curing at standard conditions, wherein the annealing step follows the curing at elevated temperatures and at atmospheric pressure. Preferably the curing takes place at a temperature of at least 0 and at most 85, preferably at least 15 and at most 80, more preferably at least 23 and at most 70, most preferably at least 30 and at most 85, for example at least 15 and at most 30 °C, for time periods that may vary and are preferably of at most 60, more preferably at most 30, even more preferably at most 15 min. The subject matter of this paragraph is mentioned in the specification as ‘A22’.
[0136] A cured form of the particles of the invention as the particles are disclosed in any one of A7 to A9 or as in any combination derived from the disclosure in this and the entire specification, may be obtained upon chemical reaction (resulting in the formation of irreversible covalent chemical bonds) or a combination of physical drying and chemical reaction. The curing of the particles of the invention may take place either at standard conditions (as these are defined in the specification), or by using heat, or by using pressure, or by applying vacuum, or by irradiation, e.g. UV-radiation, or by any combination thereof. Preferably the particles of the invention are cured at a temperature of at least 0 and at most 85, preferably at least 15 and at most 80, more preferably at least 23 and at most 70, most preferably at least 30 and at most 85, for example at least 15 and at most 30 °C, for time periods that may vary and are preferably of at most 60, more preferably at most 30, even more preferably at most 15 min. Preferably the particles of the invention are cured in the presence of a cationic initiator. Obviously, curing at elevated temperatures and at atmospheric pressure requires shorter curing time; curing may also be affected by using pressure or by applying vacuum, or by irradiation, e.g. UV-radiation, or by any combination thereof. The subject matter of this paragraph is mentioned in the specification as ‘A23’. 2024PF30083 FC
[0137] Preferably, the cured form of the particles of the invention as the particles of the invention are disclosed in any one of A7 to A9 or as in any combination derived from the disclosure in this and the entire specification, is obtained upon curing the particles of the invention in the presence of a polymer -preferably a carboxylic acid functional polymer- at standard conditions for example 12-48 h (preferably 24-48 h), and / or by heat-curing at elevated temperatures and at atmospheric pressure for example 70-80 °C for 10-60 min (preferably 15-30 min, more preferably 20 min), and / or any combination of curing at room temperature and curing at elevated temperatures; annealing steps (e.g. 50°C for 16 h) may also be included especially in between curing at elevated temperatures and at atmospheric pressure and curing at standard conditions, wherein the annealing step follows the curing at elevated temperatures and at atmospheric pressure. Preferably the curing takes place at a temperature of at least 0 and at most 85, preferably at least 15 and at most 80, more preferably at least 23 and at most 70, most preferably at least 30 and at most 85, for example at least 15 and at most 30 °C, for time periods that may vary and are preferably of at most 60, more preferably at most 30, even more preferably at most 15 min. The subject matter of this paragraph is mentioned in the specification as ‘A24’.
[0138] A cured form of the composition of the invention as the composition of the invention is disclosed in any one of A10 to A16 or as in any combination derived from the disclosure in this and the entire specification, may be obtained upon chemical reaction (resulting in the formation of irreversible covalent chemical bonds) or a combination of physical drying and chemical reaction. The curing of the composition of the invention may take place either at standard conditions (as these are defined in the specification), or by using heat, or by using pressure, or by applying vacuum, or by irradiation, e.g. UV-radiation, or by any combination thereof. Preferably the composition of the invention are cured at a temperature of at least 0 and at most 85, preferably at least 15 and at most 80, more preferably at least 23 and at most 70, most preferably at least 30 and at most 85, for example at least 15 and at most 30 °C, for time periods that may vary and are preferably of at most 60, more preferably at most 30, even more preferably at most 15 min. Preferably the composition of the invention is cured in the presence of a cationic initiator. Obviously, curing at elevated temperatures and at atmospheric pressure requires shorter curing time; curing may also be affected by using pressure or by applying vacuum, or by irradiation, e.g. UV-radiation, or by any combination thereof. The subject matter of this paragraph is mentioned in the specification as ‘A25’. 2024PF30083 FC
[0139] Preferably, the cured form of the composition of the invention as the composition of the invention are disclosed in any one of A10 to A16 or as in any combination derived from the disclosure in this and the entire specification, is obtained upon curing the composition of the invention in the presence of a polymer -preferably a carboxylic acid functional polymer- at standard conditions for example 12-48 h (preferably 24-48 h), and / or by heat-curing at elevated temperatures and at atmospheric pressure for example 70-80 °C for 10-60 min (preferably 15-30 min, more preferably 20 min), and / or any combination of curing at room temperature and curing at elevated temperatures; annealing steps (e.g. 50°C for 16 h) may also be included especially in between curing at elevated temperatures and at atmospheric pressure and curing at standard conditions, wherein the annealing step follows the curing at elevated temperatures and at atmospheric pressure. Preferably the curing takes place at a temperature of at least 0 and at most 85, preferably at least 15 and at most 80, more preferably at least 23 and at most 70, most preferably at least 30 and at most 85, for example at least 15 and at most 30 °C, for time periods that may vary and are preferably of at most 60, more preferably at most 30, even more preferably at most 15 min. The subject matter of this paragraph is mentioned in the specification as ‘A26’.
[0140] In an embodiment of the invention, there is provided an article comprising: i) an aziridinyl-functional component as disclosed in any one of A1 to A6 or as in any combination derived from the disclosure in this and the entire specification, or ii) particles as disclosed in any one of A7 to A9 or as in any combination derived from the disclosure in this and the entire specification, or iii) a composition as disclosed in any one of A10 to A16 or as in any combination derived from the disclosure in this and the entire specification. The subject matter of this paragraph is mentioned in the specification as ‘A27’.
[0141] Preferably, the article is as disclosed in A27 or as in any combination derived from the disclosure in this and the entire specification, wherein the article is selected from the group consisting of textile, glass, metal, composite, plastic, wood, engineered wood, wood-like, leather, artificial leather, paper, fibers and combinations thereof. The subject matter of this paragraph is mentioned in the specification as ‘A28’.
[0142] The specification further discloses a use of any one or any combination of the following a to c: a. an aziridinyl-functional component as disclosed in any one of A1 to A6 or as in any combination derived from the disclosure in this and the entire specification ; b. particles as disclosed in any one of A7 to A9 or as in any combination derived from the disclosure in this and the entire specification; 2024PF30083 FC c. a composition as disclosed in any one of A10 to A16 or as in any combination derived from the disclosure in this and the entire specification, as crosslinker.
[0143] The specification further discloses a use of any one or any combination of the following a to c: a. an aziridinyl-functional component as disclosed in any one of A1 to A6 or as in any combination derived from the disclosure in this and the entire specification ; b. particles as disclosed in any one of A7 to A9 or as in any combination derived from the disclosure in this and the entire specification; c. a composition as disclosed in any one of A10 to A16 or as in any combination derived from the disclosure in this and the entire specification, in coatings, paints, inks, varnishes, lubricants, adhesives, additive manufacturing, 3D- printing, textiles, waxes, fuels, photography, plastics, medical devices, and in the preparation of medical compositions.
[0144] Unless otherwise explicitly stated, any feature, element, component, embodiment, range and especially any preferred feature, preferred element, preferred embodiment, preferred range, preferred combination of ranges, preferment described in the entire specification can be combined with each other. Unless otherwise explicitly stated, any feature, element, component, embodiment, range and especially any preferred feature, preferred element, preferred embodiment, preferred range, preferred combination of ranges, preferments, and embodiments in connection with any piece of disclosure in any one of A1 to A28 disclosed in this section can be combined with each other and with any other feature, element, component, embodiment, range and especially any preferred feature, preferred element, preferred embodiment, preferred range, preferred combination of ranges, preferments, and embodiments of the invention as these are disclosed in the entire specification. All combinations of minimum and maximum values of the parameters disclosed in this section may be used to define the parameter ranges for various preferments and embodiments of the invention disclosed in this section. Unless otherwise explicitly stated, any feature, element, component, embodiment, range and especially any preferred feature, preferred element, preferred embodiment, preferred range, preferred combination of ranges, preferments, and embodiments of the invention as these are disclosed in this section and in the entire specification can be combined with each other. For all upper and lower boundaries of any parameters given in this section, the boundary value is included in each range for each parameter. All combinations of minimum and maximum values of the parameters disclosed in this section may be used to define the parameter ranges for the various preferments and embodiments disclosed in this section. 2024PF30083 FC
[0145] EXAMPLES
[0146] The invention is explained in more detail with reference to the following non-limiting examples which are by way of illustration only.
[0147] By ‘inventive examples’ is meant in the specification examples which are according to the invention.
[0148] By ‘comparative examples’ is meant in the specification examples which are not according to the invention.
[0149] All the examples shown in this section were carried out in a controlled laboratory environment at standard conditions (defined in the specification), relative humidity of 50±1 %, and airflow of < 0.1 m / s.
[0150] 1.1. Chemicals, raw materials and other materials used in the examples
[0151] Methyl methacrylate (CAS No 80-62-6), n-butyl acrylate (CAS No 141- 32-2), methacrylic acid (CAS No 201-204-4) and ammonium persulfate (CAS No 7727- 54-0), acetonitrile (CAS No. 75-05-8), tetrahydrofuran (CAS No. 109-99-9; abbreviated as THF), ammonium acetate (CAS No. 631-61-8), 2-ethyl hexyl glycidyl ether (CAS No 2461-15-6), 1 ,3-bis(1-isocyanato-1-methylethyl)benzene (CAS No 2778-42-9; abbreviated as TMXDI), 1 ,6-hexanediamine (CAS No 124-09-4), dimethylformamide (CAS No 68-12-2), bismuth(lll) neodecanoate (CAS No 34364-26-6), propylene oxide (CAS No 75-56-9), 1 ,2-epoxyhexane (CAS No 1436-34-6), triethylamine (CAS No 121- 44-8), N-methylethanolamine (CAS No 109-83-1) and acetone (CAS No. 67-64-1), were obtained from Sigma-Aldrich.
[0152] Disponil® SLS 101 SPECIAL [30 wt% solution of sodium lauryl sulfate (CAS No 151-21-3) in water] and polyTHF® 650 [polytetrahydrofurane (CAS No 25190- 06-1) with an average Mn-as reported by the supplier- of 650 g / mol] were obtained from BASF SE.
[0153] Ymer™ N120 (1 ,3-diol functional polyethyleneglycol monomethylether (CAS No. 131483-27-7) with a hydroxyl value -as reported by the supplier- of 120 mg KOH / g), Ymer™ N90 (1 ,3-diol functional polyethyleneglycol monomethylether (CAS No. 131483-27-7) with a hydroxyl value -as reported by the supplier- of 90 mg KOH / g), and Ymer™ N180 (1 ,3-diol functional polyethyleneglycol monomethylether (CAS No. 131483-27-7) with a hydroxyl value -as reported by the supplier- of 180 mg KOH / g), were obtained from Perstorp AB.
[0154] Potassium carbonate (CAS No 584-08-7), isobutylene oxide (CAS No. 558-30-5), and n-butylglycidyl ether (CAS No 2426-08-6) were obtained from Alfa Aesar (a division of Themo Fisher Scientific). 2024PF30083 FC
[0155] Ammonia aqueous solution (25 wt% solution of ammonium hydroxide in water; CAS No 1336-21-6) (abbreviated as AM-solution-25 in the specification) was obtained from Fisher Scientific. Ammonia aqueous solution (6.25 wt% in water) (abbreviated as AM-solution-6.25) was prepared by diluting the AM-solution-25 in water.
[0156] Desmodur® W [4,4'-methylenebis(cyclohexyl isocyanate); CAS No 5124-30-1), Desmodur® N 3200 (1 ,6-hexanediisocyanate-based biuret), Desmodur® ultra N 3300 (1 ,6-hexanediisocyanate-based isocyanurate), and Desmodur® ultra N 3600 (1 ,6-hexanediisocyanate-based isocyanurate) were obtained from Covestro AG.
[0157] Potassium hydroxide (CAS No. 1310-58-3) (15 wt% solution in water, was obtained from Brenntag SE.
[0158] 2-Methylaziridine (propyleneimine, CAS No 75-55-8) was obtained from Menadiona S.L.
[0159] Cardura™ E10P (glycidyl neodecanoate; CAS No 26761-45-5) was obtained from Hexion Inc.
[0160] Trans-2,3-epoxybutane (CAS No 21490-63-1) was obtained from abcr GmbH.
[0161] Polyethylene glycol monomethyl ether (CAS No. 9004-74-4) with a number average molecular weight of 500 Da was obtained from Acros (a division of Thermo Fisher Scientific).
[0162] Maxemul™ 7101 (a polyalkylene oxide block copolymer used as emulsifier) was supplied by Croda Int. PLC.
[0163] Bisphenol A diglycidyl ether (CAS No 1675-54-3) was obtained from Tokyo Chemical Industry Co., Ltd.
[0164] Voranol™ P400 polyol (polypropyleneglycol; CAS No 25322-69-4) with an average Mn-as reported by the supplier- of 400 g / mol was obtained from Dow.
[0165] Durez®-ter S-105-110 (a polyester polyol with an OH-number of 110 mg KOH / g, based on adipic acid and hexane diol) was obtained from Sumitomo Bakelite Co. Ltd.
[0166] Placcel® CD 205 PL (a polycarbonate diol; CAS No 127695-58-3) with an average Mn-as reported by the supplier- of 500 g / mol was obtained from Daicel Corporation.
[0167] The red wine used originated from southern Europe with > 13 vol% alcohol.
[0168] Ethanol 48 % v / v (food grade) was obtained from Boom B.V. (Netherlands).
[0169] Leneta Form 2C Opacity Chart, and a WC-52 Leneta Wire-Cator™ wire rod were obtained by Leneta Company, Inc. 2024PF30083
[0170] 1.2. Isocyanate conversion as followed by Fourier-Transform Infrared (FT-IR) spectroscopy
[0171] Conversion of the isocyanates in the synthesis of the examples was followed by Fourier-Transform Infrared (FT-IR) spectroscopy (Bruker ALPHA II FT-IR Spectrometer, obtained from Bruker Cooperation) by overlay of consecutive spectra until no reduction was observed in the isocyanate signal (-2260 cm-1).
[0172] 1.3. Determination of the aziridine content
[0173] The aziridine content of the examples and comparative examples was calculated by summing up the amount (in mol) of all AZIROH components in the recipe multiplied by the number of aziridine groups in an AZIROH molecule, and then divided by the total amount (in g) of i) and ii), wherein i) additives (e.g. catalysts) which do not evaporate upon the determination of the solids content, as described in 1.6, and ii) the reactants which react to form the aziridine-functional components; in the specification, and for the purpose of the determination of the aziridine content, the i) and ii) mentioned in this paragraph, are collectively mentioned as ‘entity F’. The aziridine content is given in equivalents aziridine / g entity F (abbreviated as eq aziridine / g entity F).
[0174] For instance, Inventive Example 1 contains 68.32 g of AZIROH-1 (0.3648 mol). Amount aziridine groups is 0.3648 mol. The total amount of entity F is equal to 201.66 g [=69.0 g (Desmodur® W) + 41.22 g (polyTHF®650) + 0.12 g (bismuth(lll) neodecanoate) + 68.32 g (AZIROH-1) and 23.0 g (Ymer™ N-90). The calculated aziridine content of inventive example 1 is: 0.3648 / 201.66 = 0.00181 eq aziridine / g entity F (= 1.81 meq aziridine / g entity F).
[0175] For instance, Comparative Example 1 contains 18.73 g of AZIROH-1 (0.100 mol) and 31.74 g of AZIROH-4 (0.0698 mol). Amount aziridine groups is 0.100 + 2*0.0698 = 0.2396 mol. The total amount of entity F is equal to 100.02 g [=35.14 g (Desmodur® W) + 31.74 g (AZIROH-4) + 0.02 g [bismuth(lll) neodecanoate] + 18.73 g (AZIROH-1) and 14.39 g (Ymer™ N-120). The calculated aziridine content of Comparative example 1 is: 0.2396 / 100.02 = 0.00240 eq aziridine / g entity F (= 2.40 meq aziridine / g entity F). 2024PF30083 FC
[0176] 1.4. Determination of the acid value of a polymer
[0177] The acid value of a polymer is determined according to the ASTM D1639-90(1996)e1. According to the procedure, the sample was dissolved in a good solvent, was titrated with alcoholic potassium hydroxide solution of a known concentration (KOH). The difference in titration volume between the sample and a blank is the measure of the acid value on solids, according to the following equation 1 :
[0178] AV=[(Vblank - Vsample) * NKOH * 56.1] / (W * S / 100)
[0179] (equation 1) wherein
[0180] AV is the acid value (in mg KOH / g solids), biank (in ml) is the volume of KOH solution used in the blank,SamPie (in ml) is the volume of KOH solution used in the sample, NKOH is the normality (in mol / l) of the KOH solution, W is the sample weight in g and S is the solids content of the sample in %. Measurements are performed in duplicate using a potentiometric endpoint on a Metrohm 702SM Titrino titrator (accepting the measurement if the difference between duplicates is < 0.1 mg KOH / g solids).
[0181] 1.5. Determination of the acid content of a polymer
[0182] The acid content (in meq / g solids) of a polymer is calculated from the acid value (in mg KOH / g solids) -determined as described in §1.4- of the polymer, by dividing the acid value by 56.1.
[0183] For instance, the polymer of carboxylic acid functional polyacrylic of example 1.10.1 has an acid value of 31.6 mg KOH / g solids. The acid content of this polymer is : 31.6 / 56.1 = 0.564 meq / g solids.
[0184] 1.6. Determination of the pH
[0185] The pH of a sample was determined according to the ISO 976:2013. 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 using buffer solutions of pH 7.00 and 9.21 prior to use.
[0186] 1.7. Determination of solids content
[0187] The solids content (wt%) of a composition was determined via method ISO 3251-2019. 1 g of a composition was weighed into an aluminum dish with a diameter of 75 mm. The weight loss of the dispersion was subsequently determined upon drying in an air-circulated oven (the FD 115 air-circulated oven was used and it was obtained from Binder GmbH) at 130 °C for 60 min. 2024PF30083 FC
[0188] 1.8. Determination of the scatter intensity-based average hydrodynamic diameter of the particles (‘Dynamic light scattering- DLS’)
[0189] The scatter intensity-based average hydrodynamic diameter (DH) of the particles was determined using a method derived from the ISO 22412:2017 standard with a Malvern Zetasizer Nano S90 DLS instrument that was operated under the following settings. As material, a polystyrene latex was defined with a Rl 1.590 and absorption of 0.10 with a continuous of a medium of demineralized water with an apparent viscosity of 0.8812 cP and a Rl of 1.332 at 25 °C. Measurements were performed in DTS0012 disposable cuvettes, obtained from Malvern Instruments (Malvern, Worcestershire, United Kingdom). The measurements were performed under a 173 °C back-scatter angle as an average of 3 measurements after 120 seconds equilibration, consisting of 10-15 sub-runs optimized by the machine itself. The focus point of the laser was at a fixed position of 4,65 cm, and data were analyzed using a general-purpose data fitting process. Samples were prepared by diluting 0.05 g sample (aqueous dispersion) in approximately 5 ml of demineralized water. If the sample still looks hazy, it is further diluted with distilled water until it becomes almost transparent.
[0190] 1.9. Determination of the apparent viscosity
[0191] The apparent viscosity was measured at room temperature at 60 rpm, according to ISO 2555-2018 on a Brookfield DVE-LV viscometer (single-cylinder geometry). The spindle was selected from the spindles S61 , S62, S63 or S64, using the lowest-numbered spindle (i.e. the largest spindle) that yields a reading between 10% and 100% torque.
[0192] 1.10. Preparation and assessment of the properties of the coatings
[0193] 1.10.1. Preparation of the aqueous dispersion of a carboxylic acid functional polyacrylic
[0194] An aqueous dispersion of a carboxylic acid functional polyacrylic was synthesized as follows: a 2-L four-necked flask equipped with a dosing funnel, thermometer and overhead stirrer was charged with sodium lauryl sulphate (30 wt% solids in water, 18.6 g of solution) and demineralized water (711 g). The reactor phase was placed under N2 atmosphere and heated to 82 °C. A mixture of demineralized water (112 g), sodium lauryl sulphate (30 wt% solids in water, 37.2 g of solution), methyl methacrylate (325.1 g), n-butyl acrylate (337.7 g) and methacrylic acid (34.88 g) was placed in a large feeding funnel and emulsified with an overhead stirrer (monomer feed). Ammonium persulphate (1.75 g) was dissolved in demineralized water (89.61 g) and 2024PF30083 FC placed in a small feeding funnel (initiator feed). Ammonium persulphate (1.75 g) was dissolved in demineralized water (10.5 g), and this solution was added to the reactor phase. Immediately afterwards, 5% by volume of the monomer feed was added to the reactor phase. The reaction mixture then exothermed to 85 °C and was kept at 85 °C for 5 min. Then, the residual monomer feed and the initiator feed were fed to the reaction mixture over 90 min, maintaining a temperature of 85 °C. After completion of the feeds, the monomer feed funnel was rinsed with demineralized water (18.9 g) and reaction temperature maintained at 85 °C for 45 min. Subsequently, the mixture was cooled to room temperature and brought to pH = 7.2 with AM-solution-6.25 and brought to 39.4 wt% solids with further demineralized water. The carboxylic acid functional polyacrylic has an acid value of 31 .6 mg KOH / g solids and an acid content of 0.564 meq / g solids.
[0195] This aqueous dispersion is abbreviated as X1 in the specification.
[0196] 1.10.2. Preparation of a film
[0197] An amount of 1 ) an aqueous dispersion of an example or a comparative example and an amount 2) of the aqueous dispersion X1 were mixed together under continuous stirring with an upper stirrer; the amounts were calculated such as to correspond to a molar ratio of 0.6 which molar ratio is calculated according to the following equation 2: molar ratio = (M1 * S1 * aziridine content) I (M2 * S2 * acid content) (equation 2) wherein:
[0198] M1 is the weight amount (in g) of a sample to be used of either an AZ-component (as to inventive examples), or of a comparative component to an AZ-component (as to comparative examples);
[0199] M2 is the weight amount (in g) of X1.
[0200] 51 is the solids content (in %) of a sample to be used of either an AZ-component (as to inventive examples), or of a comparative component to an AZ-component (as to comparative examples);
[0201] 52 is the solids content of X1 (in %).
[0202] Upon completion of the mixing, the resulting mixture was stirred for additional 10 min after which it was allowed to settle for 10 min to allow air bubbles to escape, thus obtaining an aqueous coating composition. 2024PF30083 FC
[0203] A 100-micron wet layer of the above prepared aqueous coating composition was applied to a Leneta Form 2C Opacity Chart (obtained from Leneta Company, Inc.) by use of a WC-52 Leneta Wire-Cator™ wire rod (obtained from Leneta Company, Inc.), and dried at 16 °C at 50% air humidity for 1 week to afford the film.
[0204] 1.10.3. Determination of the ethanol resistance (ER)
[0205] The ethanol resistance of the cured coating was tested based on the DIN 68861-1 :2011-01 method. A film was prepared on a Leneta card as described in §1.10.2.
[0206] At room temperature a filter pad (type MN 440, diameter 25 mm, obtained from Macherey-Nagel GmbH & Co. Kg) was drenched in 48 vol% ethanol, put on the coating prepared above and covered with a glass petri dish. After 4 h the cap and the pad were removed and the treated coating was rated on a scale from 0 to 5, with the following features described to each rating:
[0207] 5: test area indistinguishable from adjacent surrounding area
[0208] 4: test area distinguishable from adjacent surrounding area, only when the light source is mirrored on the test surface and is reflected towards the observer’s eye, e.g. discoloration, change in gloss and colour. No change in the surface structure.
[0209] 3: test area distinguishable from adjacent surrounding area in several viewing directions. No change in surface structure.
[0210] 2: heavy changes noticeable; however, the structure of the test surface has remained more or less undamaged.
[0211] 1 : heavy changes noticeable; the structure of the test surface has changed. 0: the tested surface was heavily changed or destroyed.
[0212] 1.10.4. Determination of the red wine resistance (RWR)
[0213] The red wine resistance of the cured coating was tested based on the DIN 68861-1 :2011- 01 method. A film was prepared on a Leneta card as described in §1.10.2. At room temperature a filter pad (type MN 440, diameter 25 mm, obtained from Macherey-Nagel GmbH & Co. Kg) was drenched in red wine, put on the coating prepared above and covered with a glass petri dish. After 6 h the cap and the pad were removed and the treated coating was rated on a scale from 0 to 5, with the following features described to each rating: 2024PF30083 FC
[0214] 5: test area indistinguishable from adjacent surrounding area
[0215] 4: test area distinguishable from adjacent surrounding area, only when the light source is mirrored on the test surface and is reflected towards the observer’s eye, e.g. discoloration, change in gloss and colour. No change in the surface structure.
[0216] 3: test area is distinguishable from adjacent surrounding area in several viewing directions. No change in surface structure.
[0217] 2: heavy changes noticeable; however, the structure of the test surface has remained more or less undamaged.
[0218] 1 : heavy changes noticeable; the structure of the test surface has changed. 0: the tested surface was heavily changed or destroyed.
[0219] 1.10.5. Determination of the water resistance (WR)
[0220] The water resistance of the cured coating was tested based on the DIN 68861-1 :2011-01 method. A film was prepared on a Leneta card as described in §1.10.2.
[0221] At room temperature a filter pad (type MN 440, diameter 25 mm, obtained from Macherey-Nagel GmbH & Co. Kg) was drenched in demineralized water, put on the coating prepared above and covered with a glass petri dish. After 16 h the cap and the pad were removed and the treated coating was rated on a scale from 0 to 5, with the following features described to each rating:
[0222] 5: test area is indistinguishable from adjacent surrounding area
[0223] 4: test area is distinguishable from adjacent surrounding area, only when the light source is mirrored on the test surface and is reflected towards the observer’s eye, e.g. discoloration, change in gloss and colour. No change in the surface structure.
[0224] 3: test area is distinguishable from adjacent surrounding area in several viewing directions. No change in surface structure.
[0225] 2: heavy changes noticeable; however, the structure of the test surface has remained more or less undamaged.
[0226] 1 : heavy changes noticeable; the structure of the test surface has changed. 0: the tested surface was heavily changed or destroyed. 2024PF30083 FC
[0227] 1.11. Preparation of (aziridinyl hydroxy)-functional organic compounds (AZIROH)
[0228] The following eight (aziridinyl hydroxy)-functional organic compounds (AZIROH) (namely AZIROH-1 , AZIROH-2, AZIROH-3, AZIROH-4, AZIROH-5, AZIROH- 6, AZI ROH-7 and AZI ROH-8) were synthesized and were subsequently used in the preparation of the AZ-component in inventive examples and in the preparation of comparative examples.
[0229] 1.11.1. Synthesis of the (aziridinyl hydroxy)-functional organic compound 1 (abbreviated as AZIROH-1)
[0230] A 1 L round bottom flask equipped with a condenser was placed under a N2 atmosphere and charged with propylene imine (80.0 g), n-butyl glycidyl ether (126.0 g) and potassium carbonate (10.00 g) and heated to 80 °C in 30 min, after which the mixture was stirred for 21 h at 80 °C. After filtration the excess of propylene imine was removed in vacuo, followed by further purification via vacuum distillation, resulting in a colorless low viscous liquid.
[0231] The formula of the AZIROH-1 is:
[0232] The chemical name of the AZIROH-1 is: 1-butoxy-3-(2-methylaziridin- 1-yl)propan-2-ol (molecular weight: 187.28 g / mol).
[0233] 1.11.2. Synthesis of the (aziridinyl hydroxy)-functional organic compound 2 (abbreviated as AZIROH-2).
[0234] A 1 L round bottom flask equipped with a condenser was placed under a N2 atmosphere and charged with propylene imine (91.0 g), 2-ethylhexylglycidyl ether (201.0 g) and potassium carbonate (10.00 g) and heated to 80 °C, after which the mixture was stirred for 47 h at 80 °C. After filtration the excess of propylene imine was removed in vacuo, followed by further purification via vacuum distillation, resulting in a colorless low viscous liquid. 2024PF30083 FC
[0235] The formula of the AZI ROH-2 is:
[0236] The chemical name of the AZI ROH-2 is: 1-((2-ethylhexyl)oxy)-3-(2- methylaziridin-1-yl)propan-2-ol (molecular weight: 243.39 g / mol).
[0237] 1.11.3. Synthesis of the (aziridinyl hydroxy)-functional organic compound 3 (abbreviated as AZIROH-3).
[0238] A 1 L round bottom flask equipped with a condenser was placed under a N2 atmosphere and charged with propylene imine (69.0 g), Cardura™ E10P (201.0 g) and potassium carbonate (7.30 g) and heated to 80 °C, after which the mixture was stirred for 24 h at 80 °C. After filtration the excess of propylene imine was removed in vacuo, resulting in a colorless low viscous liquid.
[0239] The formula of the AZI ROH-3 is:
[0240] The chemical name of the AZIROH-3 is:2-hydroxy-3-(2-methylaziridin- 1-yl)propyl neodecanoate) (molecular weight: 285.43 g / mol).
[0241] 1.11.4. Synthesis of the (aziridinyl hydroxy)-functional organic compound 4 (abbreviated as AZIROH-4).
[0242] A 2 L round bottom flask equipped with a condenser was placed under a N2 atmosphere and charged with toluene (250 g), propylene imine (325 g), Bisphenol A-diglycidyl ether (387 g) and K2CO3 (10.0 g) and heated to 70°C in 30 min, after which the mixture was stirred for 19 h at 70°C. After filtration the excess of PI was removed in vacuo, followed by further purification via vacuum distillation, resulting in a whitish solid. 2024PF30083
[0243] The formula of the AZI ROH-4 is:
[0244] The chemical name of the AZI ROH-4 is: 3,3'-((propane-2,2- diylbis(cyclohexane-4,1-diyl))bis(oxy))bis(1-(2-methylaziridin-1-yl)propan-2-ol) (molecular weight: 454.61 g / mol).
[0245] 1.11.5. Synthesis of the (aziridinyl hydroxy)-functional organic compound 5 (abbreviated as AZIROH-5).
[0246] A 1 L round bottom flask equipped with a condenser was placed under a N2 atmosphere and charged with propylene imine (242 g), 1 ,2-epoxyhexane (97.3 g) and potassium carbonate (2.80 g) and heated to 72 °C, after which the mixture was stirred for 56 h at 72 °C. After filtration the excess of propylene imine was removed in vacuo, resulting in a colorless low viscous liquid.
[0247] The formula of the AZIROH-5 is:
[0248] The chemical name of the AZIROH-5 is: 1-(2-methylaziridin-1- yl)hexan-2-ol. (molecular weight: 157.26 g / mol).
[0249] 1.11.6. Synthesis of the (aziridinyl hydroxy)-functional organic compound 6 (abbreviated as AZIROH-6).
[0250] A 20 ml round bottom flask equipped with a condenser was placed under a N2 atmosphere and charged with propylene imine (2.95 g), trans-2,3- epoxybutane (3.75 g) and potassium carbonate (1 .00 g) and heated to 55 °C, after which the mixture was stirred for 11 days at 55 °C. After filtration the excess of propylene imine was removed in vacuo, resulting in a colorless low viscous liquid. 2024PF30083
[0251] The formula of the AZI ROH-6 is:
[0252] The chemical name of the AZIROH-6 is: 3-(2-methylaziridin-1-yl)butan- 2-ol) (molecular weight: 129.20 g / mol).
[0253] 1.11.7. Synthesis of the (aziridinyl hydroxy)-functional organic compound 7 (abbreviated as AZIROH-7).
[0254] A 50 mL round bottom flask equipped with a condenser was placed under a N2 atmosphere and charged with propylene imine (10.02 g), isobutylene oxide (10.04 g) and K2CO3 (0.50 g) and heated to 55°C, after which the mixture was stirred for 96 h at 55°C. After filtration the excess of PI was removed in vacuo, followed by further purification via vacuum distillation, resulting in a colorless low viscous liquid.
[0255] The formula of the AZIROH-7 is:
[0256] The chemical name of the AZIROH-7 is: 2-methyl-1-(2-methylaziridin- 1-yl)propan-2-ol. (molecular weight: 129.20 g / mol).
[0257] 1.11.8. Synthesis of the (aziridinyl hydroxy)-functional organic compound 8 (abbreviated as AZIROH-8).
[0258] A 250 ml round bottom flask equipped with a condenser was placed under a N2 atmosphere and charged with propylene imine (57.0 g), propylene oxide (58.0 g) and water (20.0 g) was heated to 45 °C and it was maintained at this temperature for 1 h under reflux. Subsequently, the reaction mixture was allowed to stand overnight without heating. Afterwards, flakes of sodium hydroxide (20.0 g) were added to the reaction mixture. Subsequently, the reaction mixture was extracted twice with benzene using a total of 100.0 ml of benzene. Subsequently, the benzene was removed in vacuo, and the crude material left after the removal of benzene was purified via vacuum distillation to obtain a colorless low viscous liquid. 2024PF30083
[0259] The formula of the AZI ROH-8 is:
[0260] The chemical name of the AZIROH-8 is: 1-(2-methylaziridin-1- yl)propan-2-ol. (molecular weight: 115.18 g / mol).
[0261] 1.12. Preparation of examples according to the invention
[0262] 1.12.1. Inventive Example 1- Preparation of an AZ-component
[0263] A 1 L round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (69.0 g), polyTHF® 650 (20.61 g), Ymer™ N90 (23.0 g) and acetone (59.8 g). The resulting mixture was heated up to 50 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.04 g) was added to the mixture. The dosing funnel was filled with AZIROH-1 (68.32 g), and its content was slowly fed to the reaction mixture over a time period of 30 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-1 , an additional amount of acetone (13.3 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.04 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for an additionally 60 min. An extra amount of polyTHF® 650 (20.61 g) and an additional catalytic amount of 0.04 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (321.0 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 42.8 wt%, a viscosity of 55 mPa.s, a DH of 155 nm and a pH of 10.4.
[0264] The AZ-component of inventive example 1 consists of AZ1 -compounds of Formulae 2-1 to 2-4 shown in Figure 2.
[0265] The molecular weight of the AZ1-compound of Formula 2-1 of Figure 2is 2192.85 g / mol.
[0266] The molecular weight of the AZ1 -compound of Formula 2-2 of Figure 2 is 3122.18 g / mol.
[0267] The molecular weight of the AZ1-compound of Formula 2-3 of Figure 2 is 3078.13 g / mol. 2024PF30083 FC
[0268] The molecular weight of the AZ1 -compound of Formula 2-4 of Figure 2 is 3907.30 g / mol.
[0269] 1.12.2. Inventive Example 2- Preparation of an AZ-component
[0270] A 500 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (35.18 g), polyTHF® 650 (11.29 g), Ymer™ N90 (11.15 g) and acetone (35.29 g). The resulting mixture was heated up to 50 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.02 g) was added to the mixture. The dosing funnel was filled with AZIROH-5 (31.09 g), and its content was slowly fed to the reaction mixture over a time period of 30 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-5, an additional amount of acetone (6.62 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. An extra amount of polyTHF® 650 (11.29 g) and an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (160.11 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 45.5 wt%, a viscosity of 140 mPa.s, a DH of 393 nm and a pH of 8.6.
[0271] The AZ-component of inventive example 2 consists of AZ1 -compounds of Formulae 4-1 to 4-4 shown in Figure 4.
[0272] The molecular weight of the AZ1-compound of Formula 4-1 of Figure 4 is 2132.80 g / mol.
[0273] The molecular weight of the AZ1 -compound of Formula 4-2 of Figure 4 is 2990.02 g / mol.
[0274] The molecular weight of the AZ1 -compound of Formula 4-3 of Figure 4 is 3062.13 g / mol.
[0275] The molecular weight of the AZ1 -compound of Formula 4-4 of Figure 4 is 3018.08 g / mol. 2024PF30083 FC
[0276] 1.12.3. Inventive Example 3- Preparation of an AZ-component
[0277] A 1 L round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (47.12 g), polyTHF® 650 (14.07 g), Ymer™ N90 (15.29 g) and acetone (60.00 g). The resulting mixture was heated up to 50 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.03 g) was added to the mixture. The dosing funnel was filled with AZIROH-3 (71.10 g), and its content was slowly fed to the reaction mixture over a time period of 30 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-3, an additional amount of acetone (9.08 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.03 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. An extra amount of polyTHF® 650 (14.07 g) and an additional catalytic amount of 0.03 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (260.00 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 41 .7 wt%, a DH of 289 nm and a pH of 9.7.
[0278] The AZ-component of inventive example 3 consists of AZ1 -compounds of Formulae 5-1 to 5-4 shown in Figure 5.
[0279] The molecular weight of the AZ1-compound of Formula 5-1 of Figure 5 is 2389.14 g / mol.
[0280] The molecular weight of the AZ1 -compound of Formula 5-2 of Figure 5 is 3246.37 g / mol.
[0281] The molecular weight of the AZ1 -compound of Formula 5-3 of Figure 5 is 3318.47 g / mol.
[0282] The molecular weight of the AZ1 -compound of Formula 5-4 of Figure 5 is 3274.42 g / mol.
[0283] 2024PF30083 FC
[0284] 1.12.4. Inventive Example 4- Preparation of an AZ-component
[0285] A 1 L round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (47.12 g), polyTHF® 650 (14.07 g), Ymer™ N90 (15.29 g) and acetone (60.00 g). The resulting mixture was heated up to 50 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.03 g) was added to the mixture. The dosing funnel was filled with AZIROH-2 (60.60 g), and its content was slowly fed to the reaction mixture over a time period of 30 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-2, an additional amount of acetone (9.08 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.03 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. An extra amount of polyTHF® 650 (14.07 g) and an additional catalytic amount of 0.03 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (240.00 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 42.0 wt%, a DH of 193 nm and a pH of 9.7.
[0286] The AZ-component of inventive example 4 consists of AZ1 -compounds of Formulae 6-1 to 6-4 shown in Figure 6.
[0287] The molecular weight of the AZ1-compound of Formula 6-1 of Figure 6 is 2305.40 g / mol.
[0288] The molecular weight of the AZ1 -compound of Formula 6-2 of Figure 6 is 3162.29 g / mol.
[0289] The molecular weight of the AZ1 -compound of Formula 6-3 of Figure 6 is 3190.35 g / mol.
[0290] The molecular weight of the AZ1 -compound of Formula 6-4 of Figure 6 is 3234.40 g / mol.
[0291] 2024PF30083 FC
[0292] 1.12.5. Inventive Example 5- Preparation of an AZ-component
[0293] A 500 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (37.46 g), Voranol™ P400 Polyol (8.70 g), Ymer™ N90 (11.14 g) and acetone (35.29 g). The resulting mixture was heated up to 50 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.02 g) was added to the mixture. The dosing funnel was filled with AZIROH-1 (34.00 g), and its content was slowly fed to the reaction mixture over a time period of 30 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-1 , an additional amount of acetone (6.62 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. An extra amount of Voranol™ P400 Polyol (8.70 g) and an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (180.00 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 44.8 wt%, a viscosity of 276 mPa.s, a DH of 173 nm and a pH of 7.4.
[0294] The AZ-component of inventive example 5 consists of AZ1 -compounds of Formulae 7-1 to 7-4 shown in Figure 7.
[0295] The molecular weight of the AZ1-compound of Formula 7-1 of Figure 7 is 2192.85 g / mol.
[0296] The molecular weight of the AZ1 -compound of Formula 7-2 of Figure 7 is 2821.70 g / mol.
[0297] The molecular weight of the AZ1-compound of Formula 7-3 of Figure 7 is 2879.78 g / mol.
[0298] The molecular weight of the AZ1-compound of Formula 7-4 of Figure 7 is 2835.73 g / mol. 2024PF30083 FC
[0299] 1.12.6. Inventive Example 6- Preparation of an AZ-component
[0300] A 500 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with TMXDI (32.63 g), polyTHF® 650 (11.12 g), Ymer™ N90 (11.14 g) and acetone (35.29 g). The resulting mixture was heated up to 50 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.02 g) was added to the mixture. The dosing funnel was filled with AZIROH-1 (34.00 g), and its content was slowly fed to the reaction mixture over a time period of 30 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-1 , an additional amount of acetone (6.62 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. An extra amount of polyTHF® 650 (11.12 g) and an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (180.00 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 51 .6 wt%, a viscosity of 260 mPa.s, a DH of 1000 nm and a pH of 9.5.
[0301] The AZ-component of inventive example 6 consists of AZ1 -compounds of Formulae 8-1 to 8-4 shown in Figure 8.
[0302] The molecular weight of the AZ1-compound of Formula 8-1 of Figure 8 is 2156.73 g / mol.
[0303] The molecular weight of the AZ1 -compound of Formula 8-2 of Figure 8 is 2995.90 g / mol.
[0304] The molecular weight of the AZ1 -compound of Formula 8-3 of Figure 8 is 3068.01 g / mol.
[0305] The molecular weight of the AZ1 -compound of Formula 8-4 of Figure 8 is 2951.85 g / mol.
[0306] 2024PF30083 FC
[0307] 1.12.7. Inventive Example 7- Preparation of an AZ-component
[0308] A 500 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (26.67 g), Desmodur® ultra N 3300 (10.0 g), polyTHF® 650 (9.09 g), Ymer™ N90 (11.15 g) and acetone (35.29 g). The resulting mixture was heated up to 50 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.02 g) was added to the mixture. The dosing funnel was filled with AZIROH-1 (34.00 g), and its content was slowly fed to the reaction mixture over a time period of 30 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-1 , an additional amount of acetone (6.62 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. An extra amount of polyTHF® 650 (9.09 g) and an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (160.00 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 42.8 wt%, a viscosity of 80 mPa.s, a DH of 118 nm and a pH of 8.3.
[0309] The AZ-component of inventive example 7 consists of AZ2-compounds of Formulae 9-1 to 9-4 shown in Figure 9.
[0310] The molecular weight of the AZ2-compound of Formula 9-1 of Figure 9 is 2622.37 g / mol.
[0311] The molecular weight of the AZ2-compound of Formula 9-2 of Figure 9 is 3479.59 g / mol.
[0312] The molecular weight of the AZ2-compound of Formula 9-3 of Figure 9 is 3551.70 g / mol.
[0313] The molecular weight of the AZ2-compound of Formula 9-4 of Figure 9 is 3507.65 g / mol. 2024PF30083 FC
[0314] 1.12.8. Inventive Example 8- Preparation of an AZ-component
[0315] A 500 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (26.35 g), Desmodur® N 3200 (10.0 g), polyTHF® 650 (9.25 g), Ymer™ N90 (11.15 g) and acetone (35.29 g). The resulting mixture was heated up to 50 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.02 g) was added to the mixture. The dosing funnel was filled with AZIROH-1 (34.00 g), and its content was slowly fed to the reaction mixture over a time period of 30 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-1 , an additional amount of acetone (6.62 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. An extra amount of polyTHF® 650 (9.25 g) and an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (160.00 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 43.2 wt%, a viscosity of 133 mPa.s, a DH of 97.0 nm and a pH of 8.0.
[0316] The AZ-component of inventive example 8 consists of AZ2-compounds of Formulae 10-1 to 10-4 shown in Figure 10.
[0317] The molecular weight of the AZ2-compound of Formula 10-1 of Figure 10 is 2596.38 g / mol.
[0318] The molecular weight of the AZ2-compound of Formula 10-2 of Figure 10 is 3525.71 g / mol.
[0319] The molecular weight of the AZ2-compound of Formula 10-3 of Figure 10 is 3453.60 g / mol.
[0320] The molecular weight of the AZ2-compound of Formula 10-4 of Figure 10 is 3481.65 g / mol. 2024PF30083 FC
[0321] 1.12.9. Inventive Example 9- Preparation of an AZ-component
[0322] A 500 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (36.98 g), polyTHF® 650 (15.87 g), Ymer™ N90 (11.15 g) and acetone (35.29 g). The resulting mixture was heated up to 50 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.02 g) was added to the mixture. The dosing funnel was filled with AZIROH-1 (34.00 g), and its content was slowly fed to the reaction mixture over a time period of 10 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-1 , an additional amount of acetone (6.62 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. A solution of 2 g 1 ,6-hexamethylenediamine in 1.33 g water and an additional amount of acetone (6.62 g) were added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (160.10 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 45.3 wt%, a viscosity of 97 mPa.s, a DH of 130 nm and a pH of 9.4.
[0323] The AZ-component of inventive example 9 consists of AZ1 -compounds of Formulae 11-1 to 11-4 shown in Figure 11.
[0324] The molecular weight of the AZ1 -compound of Formula 11-1 of Figure 11 is 2192.85 g / mol.
[0325] The molecular weight of the AZ1 -compound of Formula 11-2 of Figure 11 is 2571.41 g / mol.
[0326] The molecular weight of the AZ1 -compound of Formula 11-3 of Figure 11 is 3500.74 g / mol.
[0327] The molecular weight of the AZ1 -compound of Formula 11-4 of Figure 11 is 3384.58 g / mol.
[0328] 2024PF30083 FC
[0329] 1.12.10. Inventive Example 10- Preparation of an AZ-component
[0330] A 500 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (40.94 g), polyTHF® 650 (5.46 g), Ymer™ N90 (11.15 g), N- methylethanolamine (3.00 g) and acetone (35.29 g). The resulting mixture was heated up to 50 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.02 g) was added to the mixture. The dosing funnel was filled with AZI ROH-1 (34.00 g), and its content was slowly fed to the reaction mixture over a time period of 15 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-1 , an additional amount of acetone (6.62 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. An extra amount of polyTHF® 650 (5.46 g) and an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate were added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (160.10 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 44.8 wt%, a viscosity of 213 mPa.s, a DH of 201 nm and a pH of 8.3.
[0331] The AZ-component of inventive example 10 consists of AZ1- compounds of Formulae 12-1 to 12-4 shown in Figure 12.
[0332] The molecular weight of the AZ1 -compound of Formula 12-1 of Figure 12 is 2192.85 g / mol.
[0333] The molecular weight of the AZ1 -compound of Formula 12-2 of Figure 12 is 2530.32 g / mol.
[0334] The molecular weight of the AZ1 -compound of Formula 12-3 of Figure 12 is 3459.65 g / mol.
[0335] The molecular weight of the AZ1 -compound of Formula 12-4 of Figure 12 is 3271.38 g / mol. 2024PF30083 FC
[0336] 1.12.11. Inventive Example 11- Preparation of an AZ-component
[0337] A 500 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (35.97 g), Placcel® CD 205 PL (9.44 g), Ymer™ N90 (11.15 g) and acetone (35.29 g). The resulting mixture was heated up to 55 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.02 g) was added to the mixture. The dosing funnel was filled with AZIROH-1 (34.00 g), and its content was slowly fed to the reaction mixture over a time period of 20 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-1 , an additional amount of acetone (6.62 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for an extra 1.5 h. An extra amount of Placcel® CD 205 PL (9.44 g) and an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (160.10 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 41.5 wt%, a viscosity of 46 mPa.s, a DH of 115 nm and a pH of 8.3.
[0338] The AZ-component of inventive example 11 consists of AZ1- compounds of Formulae 13-1 to 13-4 shown in Figure 13.
[0339] The molecular weight of the AZ1 -compound of Formula 13-1 of Figure 13 is 2192.85 g / mol.
[0340] The molecular weight of the AZ1 -compound of Formula 13-2 of Figure 13 is 2717.56 g / mol.
[0341] The molecular weight of the AZ1 -compound of Formula 13-3 of Figure 13 is 2817.65 g / mol.
[0342] The molecular weight of the AZ1 -compound of Formula 13-4 of Figure 13 is 2773.62 g / mol. 2024PF30083 FC
[0343] 1.12.12. Inventive Example 12- Preparation of an AZ-component
[0344] A 500 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (31.96 g), Durez®-ter S-105-110 (11.45 g), Ymer™ N90 (11.15 g) and acetone (35.29 g). The resulting mixture was heated up to 55 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.02 g) was added to the mixture. The dosing funnel was filled with AZIROH-1 (34.00 g), and its content was slowly fed to the reaction mixture over a time period of 20 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-1 , an additional amount of acetone (6.62 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for an extra 1.5 h. An extra amount of Durez®-ter S-105- 110 (11.45 g) and an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (160.10 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 40.7 wt%, a viscosity of 42 mPa.s, a DH of 197 nm and a pH of 9.2.
[0345] The AZ-component of inventive example 12 consists of AZ1- compounds of Formulae 14-1 to 14-4 shown in Figure 14.
[0346] The molecular weight of the AZ1 -compound of Formula 14-1 of Figure 14 is 2192.85 g / mol.
[0347] The molecular weight of the AZ1 -compound of Formula 14-2 of Figure 14 is 3214.19 g / mol.
[0348] The molecular weight of the AZ1 -compound of Formula 14-3 of Figure 14 is 3442.48 g / mol.
[0349] The molecular weight of the AZ1 -compound of Formula 14-4 of Figure 14 is 3670.77 g / mol. 2024PF30083 FC
[0350] 1.12.13. Inventive Example 13- Preparation of an AZ-component
[0351] A 500 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (34.74 g), polyTHF® 650 (9.87 g), Ymer™ N120 (11.51 g) and acetone (35.29 g). The resulting mixture was heated up to 55 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.02 g) was added to the mixture. The dosing funnel was filled with AZIROH-1 (34.00 g), and its content was slowly fed to the reaction mixture over a time period of 15 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-1 , an additional amount of acetone (6.62 g) was added. The reaction mixture was stirred at 60 °C for additionally 90 min; subsequently an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. An extra amount of polyTHF® 650 (9.87 g) and an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (160.10 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 33.1 wt%, a viscosity of 26 mPa.s, a DH of 167 nm and a pH of 9.2.
[0352] The AZ-component of inventive example 13 consists of AZ1- compounds of Formulae 15-1 to 15-4 shown in Figure 15.
[0353] The molecular weight of the AZ1 -compound of Formula 15-1 of Figure 15 is 1840.43 g / mol.
[0354] The molecular weight of the AZ1 -compound of Formula 15-2 of Figure 15 is 2769.76 g / mol.
[0355] The molecular weight of the AZ1 -compound of Formula 15-3 of Figure 15 is 2653.60 g / mol.
[0356] The molecular weight of the AZ1 -compound of Formula 15-4 of Figure 15 is 2725.71 g / mol. 2024PF30083 FC
[0357] 1.12.14. Inventive Example 14- Preparation of an AZ-component
[0358] A 500 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (36.12 g), polyTHF® 650 (8.38 g), Ymer™ N180 (13.12 g) and acetone (35.29 g). The resulting mixture was heated up to 55 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.02 g) was added to the mixture. The dosing funnel was filled with AZIROH-1 (34.00 g), and its content was slowly fed to the reaction mixture over a time period of 15 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-1 , an additional amount of acetone (6.62 g) was added. The reaction mixture was stirred at 60 °C for additionally 90 min; subsequently an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. An extra amount of polyTHF® 650 (8.38 g) and an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (160.10 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 40.3 wt%, a viscosity of 440 mPa.s, a DH of 128 nm and a pH of 9.4.
[0359] The AZ-component of inventive example 14 consists of AZ1- compounds of Formulae 16-1 to 16-4 shown in Figure 16.
[0360] The molecular weight of the AZ1 -compound of Formula 16-1 of Figure 16 is 1576.11g / mol.
[0361] The molecular weight of the AZ1 -compound of Formula 16-2 of Figure 16 is 2505.44g / mol.
[0362] The molecular weight of the AZ1 -compound of Formula 16-3 of Figure 16 is 2433.33 g / mol.
[0363] The molecular weight of the AZ1 -compound of Formula 16-4 of Figure 16 is 2389.28 g / mol. 2024PF30083 FC
[0364] 1.12.15. Inventive Example 15- Preparation of an AZ-component
[0365] A 250 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (14.51 g), polyTHF® 650 (5.44 g), Ymer™ N90 (4.33 g) and acetone (13.70 g). The resulting mixture was heated up to 55 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.01 g) was added to the mixture. The dosing funnel was filled with AZI ROH-6 (9.10 g), and its content was slowly fed to the reaction mixture over a time period of 20 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-6, an additional amount of acetone (2.57 g) was added. The reaction mixture was stirred at 60 °C for additionally 90 min; subsequently an additional catalytic amount of 0.01 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. An extra amount of polyTHF® 650 (5.44 g) and an additional catalytic amount of 0.01 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (62.13 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 42.7 wt%, a viscosity of 79 mPa.s, a DH of 320 nm and a pH of 8.8.
[0366] The AZ-component of inventive example 15 consists of AZ1- compounds of Formulae 17-1 to 17-4 shown in Figure 17.
[0367] The molecular weight of the AZ1 -compound of Formula 17-1 of Figure is 2032.64 g / mol.
[0368] The molecular weight of the AZ1 -compound of Formula 17-2 of Figure 17 is 3006.02 g / mol.
[0369] The molecular weight of the AZ1 -compound of Formula 17-3 of Figure 17 is 2889.86 g / mol.
[0370] The molecular weight of the AZ1 -compound of Formula 17-4 of Figure is 2917.92 g / mol. 2024PF30083 FC
[0371] 1.12.16. Inventive Example 16- Preparation of an AZ-component
[0372] A 250 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (11.47 g), polyTHF® 650 (4.13 g), Ymer™ N90 (3.48 g) and acetone (11.01 g). The resulting mixture was heated up to 55 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.01 g) was added to the mixture. The dosing funnel was filled with AZI ROH-7 (7.36 g), and its content was slowly fed to the reaction mixture over a time period of 20 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-7, an additional amount of acetone (2.07 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.01 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. An extra amount of polyTHF® 650 (4.13 g) and an additional catalytic amount of 0.01 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (49.96 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 40.4 wt%, a viscosity of 25 mPa.s, a DH of 205 nm and a pH of 8.4.
[0373] The AZ-component of inventive example 16 consists of AZ1- compounds of Formulae 18-1 to 18-4 shown in Figure 18.
[0374] The molecular weight of the AZ1 -compound of Formula 18-1 of Figure 18 is 2032.64 g / mol.
[0375] The molecular weight of the AZ1 -compound of Formula 18-2 of Figure 18 is 3006.02 g / mol.
[0376] The molecular weight of the AZ1 -compound of Formula 18-3 of Figure 18 is 2889.86 g / mol.
[0377] The molecular weight of the AZ1 -compound of Formula 18-4 of Figure 18 is 2845.81 g / mol.
[0378] 2024PF30083 FC
[0379] 1.12.17. Inventive Example 17- Preparation of an AZ-component
[0380] A 500 ml round bottom flask equipped with a dosing funnel, a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with Desmodur® W (38.10 g), polyTHF® 650 (14.92 g), Ymer™ N90 (11.15 g) and acetone (35.29 g). The resulting mixture was heated up to 55 °C, and subsequently a catalytic amount of bismuth(lll) neodecanoate (0.02 g) was added to the mixture. The dosing funnel was filled with AZIROH-8 (20.91 g), and its content was slowly fed to the reaction mixture over a time period of 20 min, keeping the reaction temperature below 60 °C. After completing the addition of the AZIROH-8, an additional amount of acetone (6.62 g) was added. The reaction mixture was stirred at 60 °C for 1 h; subsequently an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60 °C for additionally 60 min. An extra amount of polyTHF® 650 (14.92 g) and an additional catalytic amount of 0.02 g bismuth(lll) neodecanoate was added. The reaction mixture was stirred at 60°C until NCO-signal in infrared spectroscopy (-2260 cm-1) had disappeared. The reaction mixture was cooled to 40°C. Then, demineralized water (160.11 g) was fed into the reaction mixture. The acetone was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered. The final dispersion had a solids content of 40.8 wt%, a viscosity of 100 mPa.s, a DH of 460 nm and a pH of 8.7.
[0381] The AZ-component of inventive example 17 consists of AZ1- compounds of Formulae 19-1 to 19-4 shown in Figure 19.
[0382] The molecular weight of the AZ1 -compound of Formula 19-1 of Figure 19 is 2004.59 g / mol.
[0383] The molecular weight of the AZ1 -compound of Formula 19-2 of Figure 19 is 2977.97 g / mol.
[0384] The molecular weight of the AZ1 -compound of Formula 19-3 of Figure 19 is 2861.81 g / mol.
[0385] The molecular weight of the AZ1 -compound of Formula 19-4 of Figure 19 is 2817.76 g / mol.
[0386] 2024PF30083 FC
[0387] 1.13. Preparation of examples not according to the invention
[0388] 1.13.1. Comparative Example 1
[0389] Comparative example 1 corresponds to Example 35 of WO 2021 / 148563 A1 that was reproduced as described below.
[0390] A 500 ml round bottom flask equipped with a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with AZIROH-4 (31.74 g), AZIROH-1 (18.73 g), Desmodur® W (35.14 g) and 22.83 g of acetone. The resulting mixture was heated to 50°C, after which bismuth(lll) neodecanoate (0.02 g) was added. The mixture was allowed to exotherm to 60 °C followed by stirring for 80 min at 60°C. Samples were taken at regular intervals and the reaction progress was monitored using a Bruker Alpha FT-IR spectrometer until no change in NCO-stretch at 2200-2300 cm-1was observed. Subsequently, 14.39 g of Ymer™ N120 was added to the reaction mixture. The reaction mixture was then further reacted to complete disappearance of aforementioned NCO-stretch peak, and then acetone (25.0 g) was added to dilute the reaction mixture. Subsequently, the mixture was cooled to 40°C and demineralized water (170 g) was added gradually, yielding a bluish dispersion. The acetone was then removed from the dispersion in vacuo, and finally the pH of the dispersion was set to 11 using triethylamine. The final dispersion had a solids content of 47.9 wt%, a viscosity of 572 mPa.s, a DH of 85 nm and a pH of 11 .
[0391] The molecular weight of the aziridinyl-functional organic compound of Formula 3-1 of Figure 3 is 1353.88 g / mol.
[0392] The molecular weight of the aziridinyl-functional organic compound of Formula 3-2 of Figure 3 is 636.92 g / mol.
[0393] The molecular weight of the aziridinyl-functional organic compound of Formula 3-3 of Figure 3 is 1852.54 g / mol.
[0394] The aziridinyl-functional organic component of comparative example 1 consists of the aziridinyl-functional organic compounds of Formulae 3-1 to 3.3 shown in Figure 3, and it is not according to the invention for reasons explained below.
[0395] Each one of the aziridinyl-functional organic compounds of Formulae 3-1 and 3.2 shown in Figure 3 is not according to the claimed aziridinyl-functional organic component because: a) the aziridinyl-functional organic compound of Formula 3-1 of Figure 3 ai) it does not contain a Z group as defined in the specification, and aii) it contains more than 3 aziridinyl groups, and aiii) the two nitrogen atoms in the middle of the formula of this compound that belong to an aziridinyl group they do not belong to either a Y1- or Y2-group; in other words not all of the nitrogen atoms present in the linker of the 2024PF30083 FC aziridinyl-functional organic compound of Formula 3-1 of Figure 3 participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L3-groups, L4-groups, L5-groups, L6-groups, L7-groups, L8-groups, L9-groups, L13- groups only if sulfur atoms are present in the linker, L14-groups only if sulfur atoms are present in the linker, L15-groups only if sulfur atoms are present in the linker; two of the nitrogen atoms of the linker of the aziridinyl-functional organic compound of Formula 3- 1 of Figure 3, each participates in a 3-membered-cyclic saturated aliphatic ring which 3- membered-cyclic saturated aliphatic ring is neither L1 -groups nor L2-groups nor L3- groups nor L4-groups, nor L5-groups nor L6-groups nor L7-groups nor L8-groups nor L9-groups nor L13-groups nor L14-groups nor L15 groups; b) the aziridinyl-functional organic compound of Formulae 3-2 of Figure 3 does not contain a Z group as defined in the specification, and c) the aziridinyl-functional organic compound of Formula 3.3 of Formula 3, ci) contains more than 3 aziridinyl groups, and cii) the two nitrogen atoms in the middle of the formula of this compound do not belong to either a Y1- or Y2-group; in other words, not all of the nitrogen atoms present in the linker of the aziridinyl-functional organic compound of Formula 3-3 of Figure 3 participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L3-groups, L4- groups, L5-groups, L6-groups, L7-groups, L8-groups, L9-groups, L13-groups only if sulfur atoms are present in the linker, L14-groups only if sulfur atoms are present in the linker, L15-groups only if sulfur atoms are present in the linker; two of the nitrogen atoms of the linker of the aziridinyl-functional organic compound of Formula 3-3 of Figure 3, each participates in a 3-membered-cyclic saturated aliphatic ring which 3-membered- cyclic saturated aliphatic ring is neither L1 -groups nor L2-groups nor L3-groups nor L4- groups, nor L5-groups nor L6-groups nor L7-groups nor L8-groups nor L9-groups nor L13-groups nor L14-groups nor L15 groups.
[0396] 2024PF30083 FC
[0397] 1.13.2. Comparative Example 2
[0398] Comparative example 2 corresponds to Example 32 of WO 2021 / 148563 A1 that was reproduced as described below.
[0399] A 1 L round bottom flask equipped with a thermometer and overhead stirrer was placed under a N2 atmosphere and charged with AZIROH-1 (25.12 g), Desmodur® W (55.30 g), Ymer™ N120 (18.21 g) and polyTHF® 650 (51.36 g). The resulting mixture was heated to 50°C, after which bismuth (III) neodecanoate (0.02 g) was added. The mixture was allowed to exotherm followed by further heating to 70°C and stirring until a residual NCO level of 3.8% was reached. The mixture was then cooled to 60°C and 50.0 g of acetone was added followed by further cooling to 40°C. To the mixture was then added Vestamin® A-95 (8.31 g), flushed with 15 g of demineralized water and 1.5 g of 15% aqueous potassium hydroxide solution, and the mixture was heated to 50°C and stirred for another 15 min. Then, 280 g of demineralized water and 9.5 g of 10% aqueous sodium sulfate solution were added. The solvent was removed in vacuo to obtain a whitish dispersion. The dispersion was filtered, set to 34 % solids using demineralized water and set to pH 11 with aqueous potassium hydroxide.
[0400] The aziridinyl-functional organic component of comparative example 2 consists of the aziridinyl-functional organic compound of Formula 20-1 shown in Figure 20 and it is not according to the invention because this compound is an ionic aziridinyl- functional organic.
[0401] The molecular weight of the aziridinyl-functional organic compound of Formula 20-1 of Figure 20 is 3353.46 g / mol.
[0402] 1.13.3. Comparative Example 3
[0403] Comparative example 3 corresponds to Example 24 of WO 2021 / 148563 A1 that was reproduced as described below.
[0404] 34.7 g of AZIROH-3 was charged to a reaction flask equipped with a thermometer, together with 0.05 g of bismuth (III) neodecanoate and 400 g of dimethylformamide. The mixture was stirred with a mechanical upper stirrer under a nitrogen atmosphere and heated to 50°C. A solution of 30 g of Desmodur® ultra N 3600 in 288 g of dimethylformamide was then added dropwise in 45 min to the reaction flask. After maintaining temperature for 15 min, 16.2 g of a poly(ethylene glycol) monomethyl ether with an average Mn of 500 Da was added to the reactor, flushed with 10 ml of dimethylformamide, whereafter the mixture was heated further to 70°C. Samples were taken at regular intervals and the reaction progress was monitored using a Bruker Alpha FT-IR spectrometer until no NCO-stretch at 2200-2300 cm-1was observed. The solvent 2024PF30083 FC was removed in vacuo to obtain a clear highly viscous liquid. Subsequently, 30 g of the viscous liquid obtained in the previous step was mixed with 15 g of acetone and incubated at 50°C until a homogeneous solution was obtained. To this solution was added 0.03 g of triethylamine (TEA) and then 3.0 g of molten Maxemul™ 7101. The resulting mixture was stirred for 5 min at room temperature using an I KA T25 Digital Ultra-Turrax® mixer with S 25 N - 18G head at 2000 rpm. Then, stirring was increased to 10000 rpm and 30 g of demineralized water, brought to pH 11 using triethylamine, was added gradually to the mixture over 15 min. During this addition process, the mixer was moved around the reaction vessel continuously. After completion of the addition, the resulting dispersion was stirred at 5,000 rpm for 10 more min, and the pH of the dispersion was set to 11 with TEA.
[0405] The aziridinyl-functional organic component of comparative example 3 consists of the aziridinyl-functional organic compounds of Formulae 21-1 to 21-2 shown in Figure 21 and it is not according to the invention for reasons explained below.
[0406] The molecular weight of the aziridinyl-functional organic compound of Formula 21-1 of Figure 21 is 1360.87 g / mol.
[0407] The molecular weight of the aziridinyl-functional organic compound of Formula 21-2 of Figure 21 is 1592.07 g / mol.
[0408] Each one of the aziridinyl-functional organic compounds of Formulae 21-1 and 21-2 shown in Figure 21 is not according to the claimed aziridinyl-functional organic component because: a) the aziridinyl-functional organic compound of Formula 21-1 of Figure 21 does not contain a Z group as defined in the specification, b) the aziridinyl-functional organic compound of Formula 21-2 of Figure 21 contains a Z group as defined in the specification but this Z group is covalently connected to an oxygen atom of the linker wherein said oxygen atom of the linker belongs to an L1 -group; according to the present invention the Z group is covalently connected to either a secondary or a tertiary, or a quaternary carbon atom of the linker, via a carboncarbon single bond, or to an oxygen atom of the linker via a carbon-oxygen single bond wherein said oxygen atom of the linker belongs to any one of L6-groups, L10-groups, L11 -groups, L12-groups. 2024PF30083
[0409] 1.14. Results and Discussion
[0410] In the specification, the term ‘enhanced ethanol resistance’ (or equally ‘enhanced ER’) of a coating means that the coating demonstrates a rating of at least 4, preferably a rating of 5, when the coating’s ER’s is tested as disclosed in the specification.
[0411] In the specification, the term ‘enhanced red wine resistance’ (or equally ‘enhanced RWR’) of a coating means that the coating demonstrates a rating of at least 4, preferably a rating of 5, when the coating’s RWR is tested as disclosed in the specification.
[0412] In the specification, the term ‘enhanced water resistance’ (or equally ‘enhanced WR’) of a coating means that the coating demonstrates a rating of at least 4, preferably a rating of 5, when the coating’s WR is tested as disclosed in the specification.
[0413] Table 1 summarizes the results as to the ER, RWR and WR of the inventive and comparative examples.
[0414] Table 1
[0415] The abbreviation ‘ER’ shown in Table 1 stands for ethanol resistance.
[0416] The abbreviation ‘RWR’ shown in Table 1 stands for red wine resistance. The abbreviation ‘WR’ shown in Table 1 stands for water resistance. 2024PF30083 FC
[0417] Comparative examples 1 , 2 and 3 correspond to Example 35, Example 32 and Example 24 of WO 2021 / 148563 A1 , respectively, were the closest structural approximations to the claimed aziridinyl-functional organic component and, they were tested (as described in this specification) as to their ER, RWR and WR coating properties. The differences between Comparative example 1 (Example 35 of WO 2021 / 148563 A1) and the present invention were discussed in §13.1.1. The differences between Comparative example 2 (Example 32 of WO 2021 / 148563 A1) and the present invention were discussed in §13.1.2. The differences between Comparative example 3 (Example 24 of WO 2021 / 148563 A1) and the present invention were discussed in §13.1.3. Evidently, as shown in Table 1 , none of the comparative examples provided a solution to the technical problem.
[0418] The specification disclosed inventive examples having an aziridinyl- functional organic component consisting of AZ1 -compounds (inventive examples 1 to 6, and 9 to 17) or AZ2-compounds (inventive examples 7 and 8). From the results shown in Table 1 , it is evident that only the AZ-component of the invention provided a solution to the technical problem. More particularly, it has surprisingly been found that only when the AZ-component of the invention was used in compositions, the coatings derived from said compositions had enhanced ER also combined with enhanced RWR and WR. Thus, only the AZ-component according to the invention provided a solution to the technical problem and by achieving this, they constituted a major technological advancement in the field of paints and coatings whereas the state-of the-art failed.
Claims
2024PF30083 FCCLAIMS1. An aziridinyl-functional organic component (abbreviated as AZ-component) selected from the group consisting of i) to ii): i) aziridinyl-functional organic compounds of Formula A1 (abbreviated as AZ1 -compounds), ii) aziridinyl- functional organic compounds of Formula A2 (abbreviated as AZ2-compounds), and iii) mixtures thereof,Formula A1 Formula A2 wherein each one of the AZ1 -compounds and AZ2-compounds has a molecular weight determined as the sum of the atomic weight values of the atoms making up the molecule of an AZ1 -compound or an AZ2-compound, of at least 600 and at most 10000 g / mol, and wherein each one of Xi and X2 consists of a linker and at least one group Z, as each one of the linker and the group Z is described in a) and b), respectively: a) the linker consists of carbon, hydrogen, oxygen, nitrogen and optionally sulfur atoms that are connected via covalent bonds amongst them, wherein the covalent bonds present in the linker are selected from the group consisting of carbon-carbon single bonds, carbon-hydrogen single bonds, carbon-oxygen single bonds, carbon-nitrogen single bonds, nitrogen-hydrogen single bonds, carbon-sulfur single bonds if sulfur atoms are present, carbon-nitrogen double bonds, carbon-oxygen double bonds, carbon-carbon aromatic bonds, carbonsulfur double bonds if sulfur atoms are present, and combination thereof; and wherein the linker is covalently bonded to each one of the Y via a carbon-oxygen single bond as explained in the definition of Y, and wherein the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of groups of formula L1 (abbreviated as L1 -groups), groups of formula L2 (abbreviated as L2-groups), groups of formula L3 (abbreviated as L3-groups), groups of formula L4 (abbreviated as L4-2024PF30083 FC groups), groups of formula L5 (abbreviated as L5-groups), groups of formula L6 (abbreviated as L6-groups), groups of formula L7 (abbreviated as L7-groups), groups of formula L8 (abbreviated as L8-groups), groups of formula L9 (abbreviated as L9-groups), groups of formula L10 (abbreviated as L10-groups), groups of formula L11 (abbreviated as L11-groups), groups of formula L12(abbreviated as L12-groups), groups of formula L13 (abbreviated as L13-groups) only if sulfur atoms are present in the linker, and groups of formula L15 (abbreviated as L15-groups) only if sulfur atoms are present in the linker, and wherein the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L3-groups, L4-groups, L5-groups, L6-groups, L7-groups, L8-groups, L9-groups, L13-groups only if sulfur atoms are present in the linker, L14-groups only if sulfur atoms are present in the linker, L15-groups only if sulfur atoms are present in the linker, and wherein if sulfur atoms are present in the linker, then the sulfur atoms present in the linker participate in one or any combination of groups of L13-groups, L14-groups and L15-groups,2024PF30083 FCFormula L4 Formula L5 Formula L6Formula L7 Formula L8 Formula L9Formula L13 Formula L14 Formula L15 and wherein each one of L1 -groups, L2-groups, L3-groups, L4-groups, L5-groups, L6-groups, L7-groups, L8-groups, L9-groups, L10-groups, L11 -groups, L12-groups, L13- groups, L14-groups and L15-groups, is connected to either a secondary or tertiary or quaternary carbon via every one of the attachment points shown in each one of the L1 -groups, L2-groups, L3-groups, L4-groups, L5-groups, Legroups, L7-groups, L8-groups, L9-groups, L10-groups, L11 -groups, L12-groups, L13-groups, L14-groups and L15-groups, and2024PF30083 b) the group Z is of Formula 11Formula 11 wherein n is an integer ranging from and including 1 up to and including 100, preferably n from and including 1 up to and including 80, more preferably n ranges from and including 1 up to and including 50, even more preferably n ranges from and including 1 up to and including 30, most preferably n ranges from and including 3 up to and including 80, especially n ranges from and including 3 up to and including 50, most especially n ranges from and including 3 up to and including 30, andR’ is selected from the group consisting of hydrogen, methyl and C2-C4 saturated aliphatic hydrocarbyl, preferably R’ is selected from the group consisting of methyl and C2-C4 saturated aliphatic hydrocarbyl; and wherein the group Z is covalently connected to either a either a secondary or a tertiary, or a quaternary carbon atom of the linker, via a carbon-carbon single bond, or to an oxygen atom of the linker via a carbon-oxygen single bond wherein said oxygen atom of the linker belongs to any one of L6-groups, L10-groups, L11 -groups, L12- groups, preferably said oxygen atom of the linker belongs to any one of L6-groups and L12-groups, more preferably said oxygen atom of the linker belongs to L12- groups, and whereinY is selected from the group consisting of groups of formula Y1 (abbreviated as Y1 -groups) and groups of formula Y2 (abbreviated as Y2-groups),Formula Y12024PF30083 FCFormula Y2 whereinRi is selected from the group consisting of hydrogen and methyl; andR2 is selected from the group consisting of hydrogen, methyl, and C2-C5 saturated aliphatic hydrocarbyl; andRa is selected from the group consisting of hydrogen, methyl, and C2-C4 saturated aliphatic hydrocarbyl; andR4 is selected from the group consisting of hydrogen, methyl, and C2-C4 saturated aliphatic hydrocarbyl;Rs is selected from the group consisting of hydrogen, methyl, and C2-C18 saturated aliphatic hydrocarbyl;R’s is a Cs-Cs saturated aliphatic hydrocarbylene;Re is selected from the group consisting of hydrogen, methyl, and C2-C18 aliphatic hydrocarbyl, preferably is selected from the group consisting of hydrogen, methyl, and C2-C18 saturated aliphatic hydrocarbyl;R? is selected from the group consisting of hydrogen, methyl, C2-C18 saturated aliphatic hydrocarbyl, CH2-O-(C=O)-Rs, CH2-O-R9, and CH2-(0-CRIOHCR H)P- OR11, wherein p is an integer ranging from and including 1 up to and including 35, Rs is a C1-C18 saturated aliphatic hydrocarbyl, R9 is selected from the group consisting of methyl, C2-C18 saturated aliphatic hydrocarbyl, Rwis independently selected from the group consisting of hydrogen, methyl, ethyl, Rn is selected from the group consisting of methyl, C2-C4 saturated aliphatic hydrocarbyl; and wherein each one of the Y of the AZ1 -compounds and AZ2-compounds is covalently bonded to the oxygen of a L1 -group via a carbon-oxygen single bond, and wherein the Y in each of the AZ1 -compounds and AZ2-compounds may be the same or different to each other, preferably the Y in each one of the AZ1 -compounds and AZ2-compounds is the same.
2. The aziridinyl-functional organic component as claimed in claim 1 , wherein R is selected from the group consisting of methyl and C2-C4 saturated aliphatic hydrocarbyl.2024PF30083 FC3. The aziridinyl-functional organic component as claimed in any one of claims 1 to 2, wherein Rs is selected from the group consisting of hydrogen and methyl, preferably Rs is hydrogen.
4. The aziridinyl-functional organic component as claimed in any one of the preceding claims, wherein R? is selected from the group consisting of methyl, C2- C18 saturated aliphatic hydrocarbyl, CH2-O-(C=O)-Rs, CH2-O-R9, and CH2-(O- CRioHCRioH)p-ORii, wherein p is an integer ranging from and including 1 up to and including 35, Rs is a C1-C18 saturated aliphatic hydrocarbyl, R9 is selected from the group consisting of methyl, C2-C18 saturated aliphatic hydrocarbyl, Rwis independently selected from the group consisting of hydrogen, methyl, ethyl, R11 is selected from the group consisting of methyl, C2-C4 saturated aliphatic hydrocarbyl.
5. The aziridinyl-functional organic component as claimed in any one of claims 1 to 3, wherein R? is selected from the group consisting of C2-C18 saturated aliphatic hydrocarbyl, CH2-O-(C=O)-Rs, CH2-O-R9, and CH2-(0-CRioHCRioH)p-ORn, wherein p is an integer ranging from and including 1 up to and including 35, Rs is a C1-C18 saturated aliphatic hydrocarbyl, R9 is selected from the group consisting of methyl, C2-C18 saturated aliphatic hydrocarbyl, Rwis independently selected from the group consisting of hydrogen, methyl, ethyl, Rn is selected from the group consisting of methyl, C2-C4 saturated aliphatic hydrocarbyl.
6. The aziridinyl-functional organic component as claimed in any one of the preceding claims, wherein the covalent bonds present in the linker are selected from the group consisting of carbon-carbon single bonds, carbon-hydrogen single bonds, carbonoxygen single bonds, carbon-nitrogen single bonds, nitrogen-hydrogen single bonds, carbon-sulfur single bonds if sulfur atoms are present, carbon-nitrogen double bonds, carbon-oxygen double bonds, carbon-carbon aromatic bonds, carbon-sulfur double bonds if sulfur atoms are present, and combination thereof; preferably the covalent bonds present in the linker are selected from the group consisting of carbon-carbon single bonds, carbon-hydrogen single bonds, carbonoxygen single bonds, carbon-nitrogen single bonds, nitrogen-hydrogen single bonds, carbon-sulfur single bonds if sulfur atoms are present, carbon-nitrogen double bonds, carbon-oxygen double bonds, and carbon-sulfur double bonds if sulfur atoms are present, and combinations thereof.2024PF300837. The aziridinyl-functional organic component as claimed in any one of the preceding claims, wherein the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L7-groups, L10-groups, L11 -groups, L12-groups and L13-groups only if sulfur atoms are present in the linker, more preferably the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1-groups, L2-groups, L10-groups, L11-groups, L12-groups and L13- groups only if sulfur atoms are present in the linker, for example the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L11 -groups, L12-groups and L13- groups only if sulfur atoms are present in the linker, for example the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1-groups, L2-groups, L12-groups and L13-groups only if sulfur atoms are present in the linker.
8. The aziridinyl-functional organic component as claimed in any one of the preceding claims, wherein the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L7-groups, and L13-groups only if sulfur atoms are present in the linker, more preferably the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, and L13-groups only if sulfur atoms are present in the linker.
9. The aziridinyl-functional organic component as claimed in any one of the preceding claims, wherein if sulfur atoms are present in the linker, then the sulfur atoms present in the linker participate in L13-groups.
10. The aziridinyl-functional organic component as claimed in any one of claims 1 to 7, wherein the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L7-groups, L10-groups, L11 -groups, L12-groups and L13-groups only if sulfur atoms are present in the linker, and wherein the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L7-groups,2024PF30083 FCL10-groups, L11 -groups, L12-groups and L13-groups only if sulfur atoms are present in the linker and wherein if sulfur atoms are present in the linker, then the sulfur atoms present in the linker participate in L13-groups.
11. The aziridinyl-functional organic component as claimed in any one of claims 1 to 7, wherein the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L10-groups, L11-groups, and L12-groups, and wherein the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L10-groups, L11-groups, and L12-groups, and wherein no sulfur atoms are present in the linker.
12. The aziridinyl-functional organic component as claimed in any one of claims 1 to 7, wherein the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L11 -groups, and L12-groups, and wherein the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, L11 -groups, and L12-groups, and wherein no sulfur atoms are present in the linker.2024PF30083 FC13. The aziridinyl-functional organic component as claimed in any one of claims 1 to 7, wherein the oxygen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups and L12- groups, and wherein the nitrogen atoms present in the linker participate in one or any combination of groups selected from the group consisting of L1 -groups, L2-groups, and L12- groups, and wherein no sulfur atoms are present in the linker.
14. The aziridinyl-functional organic component as claimed in claim 1 , wherein the aziridinyl-functional organic component is selected from the group consisting of aziridinyl-functional organic compounds of Formulae 1 to 13 (Formulae 1 to 13; - Figure 1), and mixtures thereof, wherein n is an integer ranging from and including 1 up to and including 100, preferably n from and including 1 up to and including 80, more preferably n ranges from and including 1 up to and including 50, even more preferably n ranges from and including 1 up to and including 30, most preferably n ranges from and including 3 up to and including 80, especially n ranges from and including 3 up to and including 50, most especially n ranges from and including 3 up to and including 30; and wherein m is an integer ranging from and including 1 up to and including 100, preferably m ranges from and including 1 up to and including 40, more preferably m ranges from and including 5 up to and including 40; and wherein n’ is an integer ranging from and including 1 up to and including 100, preferably n’ ranges from and including 1 up to and including 10.
15. Particles comprising an aziridinyl-functional organic component as claimed in any one of claims 1 to 14.
16. A composition comprising: i) an aziridinyl-functional organic component as defined in any one of claims 1 to 14, and / or are particles as defined in claim 15, and ii) at least one more ingredient other than the aziridinyl-functional organic component and the particles.2024PF30083 FC17. A kit-of-parts comprising parts A and B which are physically separated from each other, wherein: i) the part A comprises one or any combination of an aziridinyl-functional organic component as claimed in any one of claims 1 to 14, particles as claimed in claim 15, a composition as claimed in claim 16, and ii) a polymer, wherein the part A does not comprise the polymer of the part B, and the part B does neither comprise the aziridinyl-functional organic component of part A, nor the particles of part A, nor the composition of part A.
18. A cured form of i) an aziridinyl-functional component as claimed in any one of claims 1 to 14, or ii) particles as claimed in claim 15, or iii) a composition as claimed in claim 16.
19. An article comprising: i) an aziridinyl-functional organic component as claimed in any one of claims 1 to 14, and / or ii) particles as claimed in claim 15, and / or iii) a composition as claimed in claim 16, and / or iv) a cured form as claimed in claim 18.
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