Technical Field

The present invention relates to resin compositions, kits-of-parts comprising the inventive resin composition, the use of the inventive resin compositions as well as a composite material comprising the inventive resin compositions.

Technological Background

Commonly used resin systems, for example in the production composite materials, are based on (i) free-radically polymerizable, ethylenically unsaturated compounds that are cured by means of peroxides, (ii) epoxy-amine systems, and (iii) polyurethane systems in which diisocyanates are reacted with polyols.

These systems suffer from several drawbacks.

Radically curing systems are characterized by rapid low-temperature curing, but show a relatively high shrinkage. Systems based on epoxy-amine, on the other hand, show a significantly slower curing rate at low temperatures, however, show significantly less shrinkage.

To compensate the disadvantages of the respective resin system, attempts have been made in the past to combine the two systems. This means that hybrid systems of this type are based on resin compositions which contain compounds which can be hardened according to two different types of reaction. For example, EP 2357162 A1 describes a hybrid resin system which contains a free- radically curable resin and an epoxy resin. The hardeners contain an aliphatic amine and a peroxide, such as a perester. A disadvantage of this hybrid system is that it cannot be packaged in a storage-stable manner, particularly as a two-component system. This is attributed to the fact that the peresters react quickly with amines due to their reactive carbonyl group.

A further drawback of the epoxy-amine systems and polyurethane systems is that hazardous substances such as bisphenols (e.g. bisphenol-A) and isocyanates are used. Hence, there is an ongoing need to provide resin systems with optimized mechanical properties and curing characteristics. There is further an ongoing need to provide resin systems which use less hazardous substances such as an isocyanate and bisphenol free and solvent free resin type.

The above needs are met by the resin composition and kit-of-parts of the present invention.

Summary of the invention

In one aspect, the present invention provides a resin composition comprising

(i) at least one compound comprising at least two CH-acidic methylene groups,

(ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups, and

(iii) at least one primary amine; wherein the at least one primary amine is comprised in the resin composition in an amount of at least 5 wt.-% based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

In a further aspect, the present invention provides a resin composition comprising

(i) at least one compound comprising at least two CH-acidic methylene groups,

(ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups, and

(iii) at least one primary amine; wherein the amine molar ratio (AMR) of the at least one primary amine to the at least one compound comprising at least two CH-acidic methylene groups and the at least one compound comprising at least two a,p-unsaturated carbonyl groups is at least 10% as calculated by the following formula: reactive amine protons [mol] reactive amine protons [mol] + a, unsaturated carbonyl groups [mol] + methylene protons of CH acidic methylene groups [mol]

In a further aspect, the present invention provides a kit-of-parts comprising component (a) and component (b), wherein component (a) and component (b) are arranged in such a way that the components do not come into contact with each other, and wherein component (a) comprises

(i) at least one compound comprising at least two CH-acidic methylene groups, and

(ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups; and component (b) comprises

(iii) at least one primary amine; wherein the at least one primary amine is comprised in the kit-of-parts in an amount of at least

5 wt.-% based on the combined weight of the at least one compound comprising at least two CH- acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

In a further aspect, the present invention provides a kit-of-parts comprising component (a) and component (b), wherein component (a) and component (b) are arranged in such a way that the components do not come into contact with each other, and wherein component (a) comprises

(i) at least one compound comprising at least two CH-acidic methylene groups, and

(ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups; and component (b) comprises

(iii) at least one primary amine; wherein the amine molar ratio (AMR) of the at least one primary amine to the at least one compound comprising at least two CH-acidic methylene groups and the at least one compound comprising at least two a,p-unsaturated carbonyl groups is at least 10% as calculated by the following formula: M reactive amine protons [mol] reactive amine protons [mol] + a, unsaturated carbonyl groups [mol] + methylene protons of CH acidic methylene groups [mol] In a further aspect, the present invention provides the use of the resin composition according to the present invention or the kit-of-parts according to the present invention for the production of composite materials or as adhesive.

In a further aspect, the present invention provides a composite material comprising the inventive resin composition.

Detailed description

Definitions

In order for the present invention to be readily understood, several definitions of terms used in the course of the invention are set forth below.

As used herein, the term “comprising” is to be construed as encompassing both “including” and “consisting of”, both meanings being specifically intended, and hence individually disclosed, embodiments according to the present invention.

As used herein, the articles “a” and “an” preceding an element or component are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore, “a” or “an” is to be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.

As used herein, the term “about” modifying the quantity of a substance, ingredient, component, or parameter employed refers to variation in the numerical quantity that can occur, for example, through typical measuring and handling procedures, e.g., liquid handling procedures used for making concentrates or solutions. Furthermore, variation can occur from inadvertent error in measuring procedures, differences in the manufacture, source, or purity of the ingredients employed to carry out the invention. In one embodiment, the term “about” means within 10% of the reported numerical value. In a more specific embodiment, the term “about” means within 5% of the reported numerical value.

As already outlined above, the present invention pertains to a resin composition and a kit-of-parts with an amount of the at least one primary amine of at least 5 wt.-%.

Specifically, the present invention pertains to a resin composition comprising

(i) at least one compound comprising at least two CH-acidic methylene groups, (ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups, and

(iii) at least one primary amine; wherein the at least one primary amine is comprised in the resin composition in an amount of at least 5 wt.-% based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

The resin composition according to the present invention may suitably be provided as a kit-of-parts. Hence, the present invention further pertains to a kit-of-parts comprising component (a) and component (b), wherein component (a) and component (b) are arranged in such a way that the components do not come into contact with each other, and wherein component (a) comprises

(i) at least one compound comprising at least two CH-acidic methylene groups, and

(ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups; and component (b) comprises

(iii) at least one primary amine; wherein the at least one primary amine is comprised in the kit-of-parts in an amount of at least 5 wt.-% based on the combined weight of the at least one compound comprising at least two CH- acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

Furthermore, the present invention further pertains to a resin composition and a kit-of-parts wherein the amine molar ratio (AMR) is at least 10%.

Specifically, the present invention provides a resin composition comprising

(i) at least one compound comprising at least two CH-acidic methylene groups,

(ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups, and

(iii) at least one primary amine; wherein the amine molar ratio (AMR) of the at least one primary amine to the at least one compound comprising at least two CH-acidic methylene groups and the at least one compound comprising at least two a,p-unsaturated carbonyl groups is at least 10% as calculated by the following formula: reactive amine protons [mol] reactive amine protons [mol] + a, unsaturated carbonyl groups [mol] + methylene protons of CH acidic methylene groups [mol]

Accordingly, the present invention further pertains to a kit-of-parts comprising component (a) and component (b), wherein component (a) and component (b) are arranged in such a way that the components do not come into contact with each other, and wherein component (a) comprises

(i) at least one compound comprising at least two CH-acidic methylene groups, and

(ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups; and component (b) comprises

(iii) at least one primary amine; wherein the amine molar ratio (AMR) of the at least one primary amine to the at least one compound comprising at least two CH-acidic methylene groups and the at least one compound comprising at least two a,p-unsaturated carbonyl groups is at least 10% as calculated by the following formula: reactive amine protons [mol] reactive amine protons [mol] + a, p unsaturated carbonyl groups [mol] + methylene protons of CH acidic methylene groups [mol]

Therefore, the present invention provides resin compositions which are free of isocyanates and bisphenol and further do not include solvents, and further exhibit excellent mechanical properties.

It has been found that it is possible to achieve these advantages using resin compositions in which a Michael addition (N- and I or C-Michael-Addition) as well as an enamine reaction can take place and in which the primary amine is used in certain amounts. In the following, the basic reactions which can take place between the reactants comprised in the inventive resin composition: a) C-Michael addition (compound comprising at least two CH-acidic methylene groups + compound comprising at least two a,p-unsaturated carbonyl groups). b) Aza-Michael addition (compound comprising at least two a,p-unsaturated carbonyl groups + primary amine). c) Enamine reaction (compound comprising at least two CH-acidic methylene groups + primary amine).

While the following compounds and embodiments of the present invention are described in the context of the inventive resin compositions, the following description shall likewise apply to the kits- of-parts according to the present invention. Moreover, embodiments described in the context of one of the inventive resin compositions are applicable to each of the resin compositions according to the present invention.

In one embodiment, the present invention provides a resin composition comprising

(i) at least one compound comprising at least two CH-acidic methylene groups,

(ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups, and

(iii) at least one primary amine selected from cycloaliphatic amines, cycloaromatic amines, and combinations thereof; wherein the at least one primary amine is comprised in the resin composition in an amount of from 5 wt.-% to 25 wt.-% based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p- unsaturated carbonyl groups, and the at least one primary amine.

In one embodiment, the present invention provides a kit-of-parts comprising component (a) and component (b), wherein component (a) and component (b) are arranged in such a way that the components do not come into contact with each other, and wherein component (a) comprises

(i) at least one compound comprising at least two CH-acidic methylene groups, and

(ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups; and component (b) comprises

(iii) at least one primary amine selected from cycloaliphatic amines, cycloaromatic amines, and combinations thereof; wherein the at least one primary amine is comprised in the kit-of-parts in an amount of from 5 wt.-% to 25 wt.-% based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

Primary amines

The resin compositions according to the present invention comprise at least one primary amine.

Suitable primary amines include di- and polyamines, i.e. amines which include at least two primary amine groups.

In one embodiment, the at least one primary amine is selected from aliphatic amines, cycloaliphatic amines, cycloaromatic amines, and combinations thereof. In one embodiment, the at least one primary amine is selected from cycloaliphatic amines, cycloaromatic amines, and combinations thereof. The aliphatic amines, cycloaliphatic amines, cycloaromatic amines suitably include at least two primary amine groups, such as two primary amine groups (“diamines”), three primary amine groups (“triamines”), or four primary amine groups (“tetraamines”).

In one embodiment, the at least one primary amine is an aliphatic amine such as an aliphatic diamine, an aliphatic triamine, or an aliphatic tetraamine. In one embodiment, the aliphatic amine comprises at least two primary amine groups, such as two primary amine groups, three primary amine groups, four primary amine groups, five primary amine groups, or six primary amine groups. Preferably, the aliphatic amine comprises two primary amine groups. Aliphatic amines also include aliphatic amines in which one or more aliphatic groups are connected via an ether linkage, so called etheramines. Ether amines are commercially available under the tradename Jeffamine®, e.g.

Jeffamine EDR-104 (oxybis(ethylamine)), Jeffamine D230, and Jeffamine HK511 : In one embodiment, the aliphatic amine is selected from the group consisting of diaminopropane, diaminobutane, diaminopentane, diaminohexane, Jeffamine EDR-104, Jeffamine D230, Jeffamine HK511 , 4,7,10-Trioxatridecane-1 ,13-diamine (TTD), 4,9-Dioxadodecane-1 ,12-diamine (DODA), and combinations thereof. In one embodiment, the aliphatic amine is selected from the group consisting of 1 ,3-diaminopropane, 1 ,4-diaminobutane, 1 ,5-diaminopentane, 1 ,6-diaminohexane, Jeffamine EDR-104, Jeffamine D230, Jeffamine HK511 , 4,7, 10-Trioxatridecane-1 ,13-diamine (TTD), 4,9- Dioxadodecane-1 ,12-diamine (DODA), and combinations thereof.

In one embodiment, the at least one primary amine is a cycloaliphatic amine, such as a cycloaliphatic diamine, a cycloaliphatic triamine, or a cycloaliphatic tetraamine. In one embodiment, the cycloaliphatic amine comprises at least two primary amine groups, such as two primary amine groups, three primary amine groups, four primary amine groups, five primary amine groups, or six primary amine groups. Preferably, the cycloaliphatic amine comprises two primary amine groups. In one embodiment, the cycloaliphatic amine is selected from the group consisting of isophorone diamine (IPDA), 1 ,2-diaminocyclohexane, 1 ,3-diaminocyclohexane, 1 ,4-diaminocyclohexane, 4- methylcyclohexane-1 ,3-diamine, 4-methylcyclohexane-1 ,2-diamine, 2-methylcyclohexane-1 ,3- diamine, 3-methylcyclohexane-1 ,2-diamine, 1 ,3-bis(aminomethyl)cyclohexane, 1 ,3- cyclopentanediamine, 4,4'-methylenebis(cyclohexaneamine), 4,4'-methylenebis(2- methylcyclohexaneamine), 4,4'-methylenebis(2-ethylcyclohexaneamine), 4,4'-methylenebis(2,6- dimethylcyclohexaneamine), 4,4'-methylenebis(2,6-diethylcyclohexaneamine), 4,4'- methylenebis(2,6-diisopropyl-cyclohexaneamine), 4,4'-methylenebis(2-methyl-6-isopropyl- cyclohexaneamine), 4,4'-methylenebis(2-ethyl-6-methyl-cyclohexaneamine), 4,4'-methylenebis(2- chloro-cyclohexaneamine), 2,4-diethyl-6-methyl-1 ,3-cyclohexanediamine, 4,6-diethyl-2-methyl-1 ,3- cyclohexanediamine, and combinations thereof. Preferably, the cycloaliphatic amine is isophorone diamine (IPDA).

In one embodiment, the at least one primary amine is a cycloaromatic amine such as a cycloaromatic diamine, a cycloaromatic triamine, or a cycloaromatic tetraamine. In one embodiment, the cycloaromatic amine comprises at least two primary amine groups, such as two primary amine groups, three primary amine groups, four primary amine groups, five primary amine groups, or six primary amine groups. Preferably, the cycloaromatic amine comprises two primary amine groups. In one embodiment, the cycloaromatic amine is selected from the group consisting of m-Xylylenediamine (MXDA), 1 ,2-diaminobenzene, 1 ,3-diaminobenzene, 1 ,4-diaminobenzene, 4- methyl-1 ,3-phenylenediamine, 4-methyl-1 ,2-phenylenediamine, 2-methyl-1 ,3-phenylenediamine, 3- methyl-1 ,2-phenylenediamine, 4,4'-methylenedianiline, 4,4'-methylenebis(2-methylaniline), 4,4'- methylenebis(2-ethylaniline), 4,4'-methylenebis(2,6-dimethylaniline), 4,4'-methylenebis(2,6- diethylaniline), 4,4'-methylenebis(2,6-diisopropylaniline), 4,4'-methylenebis(2-methyl-6- isopropylaniline), 4,4'-methylenebis(2-ethyl-6-methyl-aniline), 4,4'-methylenebis(2-chloroaniline), 3,5-diethyltoluene-2,4-diamine, 3,5-diethyltoluene-2,6-diamine, and combinations thereof. Preferably, the cycloaromatic amine is m-Xylylenediamine (MXDA).

The inventors surprisingly found that certain amounts of the at least one primary amine in the resin composition is beneficial in terms of mechanical properties. In particular, increasing the amount of the at least one primary amine in the resin composition unexpectedly yielded excellent mechanical properties such as a high glass transition temperature.

Without wishing to be bound to any theory, it is believed that an amount of at least 5 wt.-% of the at least one primary amine based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p- unsaturated carbonyl groups, and the at least one primary amine leads to enhanced mechanical properties, such as a high glass transition temperature, of the cured resin composition.

Accordingly, in one embodiment, the at least one primary amine is comprised in the resin composition in an amount of at least 5 wt.-% based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

The at least one primary amine may suitably be comprised in the resin composition in an amount of at least 5 wt.-%, at least 6 wt.-%, at least 7 wt.-%, at least 8 wt.-%, at least 9 wt.-%, at least

10 wt.-%, at least 11 wt.-%, at least 12 wt.-%, at least 13 wt.-%, at least 14 wt.-%, at least 15 wt.-%, at least 16 wt.-%, at least 17 wt.-%, at least 18 wt.-%, at least 19 wt.-%, or at least 20 wt.-%, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

In one embodiment, the at least one primary amine is comprised in the resin composition in an amount of from 5 wt.-% to 25 wt.-%, such as from 5 wt.-% to 20 wt.-%, from 6 wt.-% to 18 wt.-%, from 7 wt.-% to 16 wt.-%, from 8 wt.-% to 14 wt.-%, or from 9 wt.-% to 12 wt.-%, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine. In one embodiment, the at least one primary amine is comprised in the resin composition in an amount of about 5 wt.-%, about 6 wt.-%, about 7 wt.-%, about 8 wt.-%, about 9 wt.-%, about 10 wt.-%, about 11 wt.-%, about 12 wt.-%, about 13 wt.-%, about 14 wt.-%, about 15 wt.-%, about

16 wt.-%, about 17 wt.-%, about 18 wt.-%, about 19 wt.-%, about 20 wt.-%, about 21 wt.-%, about

22 wt.-%, about 23 wt.-%, about 24 wt.-%, or about 25 wt.-%, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

In one embodiment, the at least one primary amine is a cycloaliphatic amine, such as a cycloaliphatic diamine, a cycloaliphatic triamine, or a cycloaliphatic tetraamine, and comprised in the resin composition in an amount of from 5 wt.-% to 25 wt.-%, such as from 5 wt.-% to 20 wt.-%, from 6 wt.-% to 18 wt.-%, from 7 wt.-% to 16 wt.-%, from 8 wt.-% to 14 wt.-%, or from 9 wt.-% to 12 wt.-%, based on the combined weight of the at least one compound comprising at least two CH- acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

In one embodiment, the at least one primary amine is a cycloaliphatic diamine, preferably isophorone diamine (IPDA), and comprised in the resin composition in an amount of from 5 wt.-% to 25 wt.-%, such as from 5 wt.-% to 20 wt.-%, from 6 wt.-% to 18 wt.-%, from 7 wt.-% to 16 wt.-%, from 8 wt.-% to 14 wt.-%, or from 9 wt.-% to 12 wt.-%, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

In one embodiment, the at least one primary amine is isophorone diamine (IPDA) and comprised in the resin composition in an amount of from 6 wt.-% to 18 wt.-%, preferably from 7 wt.-% to 16 wt.- %, more preferably from 8 wt.-% to 14 wt.-%, and even more preferably from 9 wt.-% to 12 wt.-%, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

In one embodiment, the at least one primary amine is a cycloaromatic amine, such as a cycloaromatic diamine, a cycloaromatic triamine, or a cycloaromatic tetraamine, and comprised in the resin composition in an amount of from 5 wt.-% to 25 wt.-%, such as from 5 wt.-% to 20 wt.-%, from 6 wt.-% to 18 wt.-%, from 7 wt.-% to 16 wt.-%, from 8 wt.-% to 14 wt.-%, or from 9 wt.-% to 12 wt.-%, based on the combined weight of the at least one compound comprising at least two CH- acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

In one embodiment, the at least one primary amine is a cycloaromatic diamine, preferably m- Xylylenediamine (MXDA), and comprised in the resin composition in an amount of from 5 wt.-% to 25 wt.-%, such as from 5 wt.-% to 20 wt.-%, from 6 wt.-% to 18 wt.-%, from 7 wt.-% to 16 wt.-%, from 8 wt.-% to 14 wt.-%, or from 9 wt.-% to 12 wt.-%, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

In one embodiment, the at least one primary amine is m-Xylylenediamine (MXDA) and comprised in the resin composition in an amount of from 6 wt.-% to 18 wt.-%, preferably from 7 wt.-% to 16 wt.- %, more preferably from 8 wt.-% to 14 wt.-%, and even more preferably from 9 wt.-% to 12 wt.-%, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

In one embodiment, the at least one primary amine and the at least one compound comprising at least two a,p-unsaturated carbonyl groups are present in the resin composition at a weight ratio of from 1 :18 to 1 :2. Suitable weight ratios of the at least one primary amine and the at least one compound comprising at least two a,p-unsaturated carbonyl groups include 1 :18, 1 :17, 1 :16, 1 :15, 1 :14, 1 :13, 1 :12, 1 :11 , 1 :10, 1 :9, 1 :8, 1 :7, 1 :6, 1 :5, 1 :4, 1 :3, and 1 :2.

In one embodiment, the at least one primary amine and the at least one compound comprising at least two a,p-unsaturated carbonyl groups are present in the resin composition at a weight ratio of from 1 :12 to 1 :2.5. In one embodiment, the at least one primary amine and the at least one compound comprising at least two a,p-unsaturated carbonyl groups are present in the resin composition at a weight ratio of from 1 :10 to 1 :3. In one embodiment, the at least one primary amine and the at least one compound comprising at least two a,p-unsaturated carbonyl groups are present in the resin composition at a weight ratio of from 1 :7 to 1 :4.

In one embodiment, the at least one primary amine and the at least one compound comprising at least two CH-acidic methylene groups are present in the resin composition at a weight ratio of from 1 :12 to 1 :2. Suitable weight ratios of the at least one primary amine and the at least one compound comprising at least two CH-acidic methylene groups include 1 :12, 1 :11 , 1 :10, 1 :9, 1 :8, 1 :7, 1 :6, 1 :5, 1 :4, 1 :3, and 1 :2. In one embodiment, the at least one primary amine and the at least one compound comprising at least two CH-acidic methylene groups are present in the resin composition at a weight ratio of from 1 :8 to 1 .2.2. In one embodiment, the at least one primary amine and the at least one compound comprising at least two CH-acidic methylene groups are present in the resin composition at a weight ratio of from 1 :6 to 1 :2.4. In one embodiment, the at least one primary amine and the at least one compound comprising at least two CH-acidic methylene groups are present in the resin composition at a weight ratio of from 1 :4 to 1 :2.6.

The inventors further surprisingly found that a certain amine molar ratio (AMR) of the at least one primary amine to the at least one compound comprising at least two CH-acidic methylene groups and the at least one compound comprising at least two a,p-unsaturated carbonyl groups is beneficial in terms of mechanical properties. In particular, increasing the amine molar ratio (AMR) of the at least one primary amine to the at least one compound comprising at least two CH-acidic methylene groups and the at least one compound comprising at least two a,p-unsaturated carbonyl groups unexpectedly yielded excellent mechanical properties such as a high glass transition temperature.

Without wishing to be bound to any theory, it is believed that an amine molar ratio (AMR) of the at least one primary amine of at least 10% to the at least one compound comprising at least two CH- acidic methylene groups and the at least one compound comprising at least two a,p-unsaturated carbonyl groups leads to enhanced mechanical properties, such as a high glass transition temperature, of the cured resin composition.

Accordingly, in one embodiment, the amine molar ratio (AMR) of the at least one primary amine to the at least one compound comprising at least two CH-acidic methylene groups and the at least one compound comprising at least two a,p-unsaturated carbonyl groups is at least 10% as calculated by the following formula: reactive amine protons [mol] reactive amine protons [mol] + a, unsaturated carbonyl groups [mol] + methylene protons of CH acidic methylene groups [mol]

Thus, the amine molar ratio (AMR) is calculated taking into account the molar amount of the reactive amine protons in the at least one primary amine, the molar amount of the a,p-unsaturated carbonyl groups in the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the molar amount of the methylene protons of the CH-acidic methylene groups in the at least one compound comprising at least two CH-acidic methylene groups. For example, if the primary amine compound has two primary amine groups, the molar amount of the reactive amine protons is 4 x the molar amount of the primary amine.

For example, if the compound comprising at least two a,p-unsaturated carbonyl groups comprises three acrylate groups, the molar amount of the a,p-unsaturated carbonyl groups is 3 x the molar amount of the compound comprising at least two a,p-unsaturated carbonyl groups.

For example, if the compound comprising at least two CH-acidic methylene groups comprises three acetoacetate groups -C(O)-CH2-C(O)-, the molar amount of the methylene protons of the CH- acidic methylene groups is 6 x the molar amount of the compound comprising at least two CH- acidic methylene groups.

An amine molar ratio (AMR) of at least 10% includes at least 11%, at least 12%, at least 12%, at least 13%, at least 14%, at least 15%, at least 16%, at least 17%, at least 18%, at least 19%, at least 20%, at least 21%, at least 22%, at least 23%, at least 24%, or at least 25%.

In one embodiment, the amine molar ratio (AMR) is at least 11%, at least 12%, at least 13%, at least 14%, at least 15%, at least 16%, or at least 17%.

Preferably, the amine molar ratio (AMR) is at least 12%. More preferably, the amine molar ratio (AMR) is at least 14%. Even more preferably, the amine molar ratio (AMR) is at least 16%.

In one embodiment, the amine molar ratio (AMR) is from 10% to 25% such as from 11% to 24%, 12% to 23%, 13% to 22%, 14% to 21%, 15% to 20%, or 16% to 19%.

Compound comprising at least two CH-acidic methylene groups

The resin compositions according to the present invention comprise at least one compound comprising at least two CH-acidic methylene groups.

In one embodiment, said compound comprises two CH-acidic methylene groups. In one embodiment, said compound comprises three CH-acidic methylene groups. In one embodiment, said compound comprises four CH-acidic methylene groups. In one embodiment, said compound comprises five CH-acidic methylene groups. In one embodiment, said compound comprises six CH- acidic methylene groups.

“CH-acidic methylene group” refers to a methylene group which is adjacent to one or two electron withdrawing groups, preferably two electron withdrawing groups, such as a carbonyl group. In one embodiment, the CH-acidic methylene group is a 2-methylene-1 ,3-dicarbonyl group such as a acetoacetate group. As such, the at least one compound comprising at least two CH-acidic methylene groups can be a compound comprising two 2-methylene-1 ,3-dicarbonyl groups (e.g. two acetoacetate groups), three 2-methylene-1 ,3-dicarbonyl groups (e.g. three acetoacetate groups), four 2-methylene-1 ,3-dicarbonyl groups (e.g. four acetoacetate groups), five 2-methylene-1 ,3- dicarbonyl groups (e.g. five acetoacetate groups), or six 2-methylene-1 ,3-dicarbonyl groups (e.g. six acetoacetate groups).

Suitable compounds comprising at least two CH-acidic methylene groups include 1 ,4-butanediol diacetoacetate, 1 ,6-hexanediol diacetoacetate, neopentylglycol diacetoacetate, cyclohexane dimethanol diacetoaceta, 2-ethyl-2-butyl-1 ,3-propanediol diacetoacetate, cyclohexanedimethanol diacetoacetate, trimethylolpropane triacetoacetate, glycerol triacetoacetate, polycaprolactone triacetoacetate, ethoxylated or propoxylated trimethylol propane triacetoacetate, ethoxylated or propoxylated glycerol triacetoacetate, pentaerythritol tetraacetoacetate, ethoxylated or propoxylated pentaerythritol tetraacetoacetate, ditrimethylolpropane tetraacetoacetate, dipentaerythritol hexaacetoacetate, and combinations thereof.

In one embodiment, the compound comprising at least two CH-acidic methylene groups is trimethylolpropane triacetoacetate (CAS 22208-25-9):

In one embodiment, the resin composition comprises from 20 wt.-% to 40 wt.-% of the at least one compound comprising at least two CH-acidic methylene groups, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine. Preferably, the resin composition comprises from 30 wt.-% to 36 wt.-% of the at least one compound comprising at least two CH-acidic methylene groups, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine. In one embodiment, the compound comprising at least two CH-acidic methylene groups is trimethylolpropane triacetoacetate and is comprised in the resin composition in an amount of from 20 wt.-% to 40 wt.-%, preferably from 30 wt.-% to 36 wt.-%, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

Compound comprising at least two a,B-unsaturated carbonyl groups

The resin compositions according to the present invention comprise at least one compound comprising at least two a,p-unsaturated carbonyl groups.

In one embodiment, said compound comprises two a,p-unsaturated carbonyl groups. In one embodiment, said compound comprises three a,p-unsaturated carbonyl groups. In one embodiment, said compound comprises four a.p-unsaturated carbonyl groups. Particularly, said compound is selected from a diacrylate, a triacrylate, a tetraacrylate, and combinations thereof. a,p-unsaturated carbonyl groups include vinyl ketones, acrylates, and acrylamides. In one embodiment, the compound comprising at least two a,p-unsaturated carbonyl groups comprises at least two groups selected from the group consisting of vinyl ketones, acrylates, acrylamides, and combinations thereof.

Suitable compounds comprising at least two a,p-unsaturated carbonyl groups include ethanediol diacrylate, 1 ,3-propanediol diacrylate, 1 ,4-butanediol acrylate, poly(butanediol)diacrylate, polybutadiene diacrylate, 3-methyl-1 ,5-pentanediol diacrylate, 1 ,6-hexanediol diacrylate, ethylene or propylene glycol diacrylate, diethylene or dipropylene glycol diacrylate, triethylene or tripropylene glycol diacrylate, tertraethylene or tetrapropylene glycol diacrylate, polyethylene or polypropylene glycol diacrylate, resorcinol diglycidyl ether diacrylate, neopentyl glycol diacrylate, cyclohexane dimethanol diacrylate, ethoxylated or propoxylated neopentyl glycol diacrylate, ethoxylated or propoxylated cyclohexanedimethanol diacrylate, acrylated epoxy diacrylate, aryl and aliphatic urethane diacrylate .polyester diacrylate, trimethylolpropane triacrylate, glycerol triacrylate, ethoxylated or propoxylated trimethylolpropane triacrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, ethoxylated or propoxylated glycerol triacrylate, pentaerythritol triacrylate, aryl and aliphatic urethane triacrylates, melamine triacrylates, epoxy novolac triacrylates, pentaerythritol tetraccrylate, ethoxylated or propoxylated pentaerythritol tetraacrylate, dipentaerythritol tetraacrylate, ethoxylated or propoxylated dipentaerythritol tetraacrylate, aryl and aliphatic urethane tetraacrylates, melamine tetraacrylates, epoxy novolac tetraacrylates, and combinations thereof. In one embodiment, the at least one compound comprising at least two a,p-unsaturated carbonyl groups is trimethylolpropane triacrylate (CAS 15625-89-5):

In one embodiment, the resin composition comprises from 45 wt.-% to 65 wt.-% of the at least one compound comprising at least two a,p-unsaturated carbonyl groups, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine. Preferably, the resin composition comprises from 50 wt.-% to 60 wt.-% of the at least one compound comprising at least two a,p-unsaturated carbonyl groups, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

In one embodiment, the at least one compound comprising at least two a,p-unsaturated carbonyl groups is trimethylolpropane triacrylate and is comprised in the resin composition in an amount of from 45 wt.-% to 65 wt.-%, preferably from 50 wt.-% to 60 wt.-%, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

Resin compositions

In one embodiment, the resin composition comprises

(i) from 20 wt.-% to 40 wt.-% of at least one compound comprising at least two CH-acidic methylene groups,

(ii) from 45 wt.-% to 65 wt.-% of at least one compound comprising at least two a,p- unsaturated carbonyl groups, and

(iii) from 5 wt.-% to 25 wt.-% of at least one primary amine; each based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p- unsaturated carbonyl groups, and the at least one primary amine.

In one embodiment, the resin composition comprises

(i) from 20 wt.-% to 40 wt.-% of trimethylolpropane triacetoacetate,

(ii) from 45 wt.-% to 65 wt.-% of trimethylolpropane triacrylate, and

(iii) from 5 wt.-% to 25 wt.-% of isophorone diamine (IPDA); each based on the combined weight of constituents (i) to (iii).

In one embodiment, the resin composition comprises

(i) from 20 wt.-% to 40 wt.-% of trimethylolpropane triacetoacetate,

(ii) from 45 wt.-% to 65 wt.-% of trimethylolpropane triacrylate, and

(iii) from 5 wt.-% to 25 wt.-% of m-Xylylenediamine (MXDA); each based on the combined weight of constituents (i) to (iii).

In one embodiment, the resin composition comprises

(i) trimethylolpropane triacetoacetate,

(ii) trimethylolpropane triacrylate, and

(iii) isophorone diamine (IPDA); wherein the amine molar ratio (AMR) of isophorone diamine (IPDA) to trimethylolpropane triacetoacetate and trimethylolpropane triacrylate is at least 10% as calculated by the following formula: reactive amine protons [moll

AMR = - : - : - _F — - - - - f - n- reactive amine protons [molj + acrylate groups [molj + methylene protons of the acetoacetate groups [mol] In one embodiment, the resin composition comprises

(iv) trimethylolpropane triacetoacetate,

(v) trimethylolpropane triacrylate, and

(vi) m-Xylylenediamine (MXDA); wherein the amine molar ratio (AMR) of m-Xylylenediamine (MXDA) to trimethylolpropane triacetoacetate and trimethylolpropane triacrylate is at least 10% as calculated by the following formula: reactive amine protons [moll

AMR = - : - : - _F — - - - - f - rr reactive amine protons [molj + acrylate groups [molj +methylene protons of the acetoacetate groups [mol]

In one embodiment, the resin composition has a glass-transition temperature Tg of at least 110°C as determined by differential scanning calorimetry (DSC) (25-160°C at 20 K/min) after curing such as at about 160°C for at least 1 h, such as for at least 1.5 h e.g. for 1 h 40 min.

The glass-transition temperature Tg of the cured resin composition can be determined by differential scanning calorimetry (DSC) at a heating rate of 20 K/min at a temperature range of 25- 160°C, as known in the art and described e.g. in ISO11357-1 .

In one embodiment, the resin composition has a glass-transition temperature Tg of at least 110°C as determined by thermomechanical analysis (TMA) after curing, e.g. at a temperature of about 120°C for at least 4 h such as 12 h.

The glass-transition temperature Tg of the cured resin composition can be determined by thermomechanical analysis (TMA) (1 ^st run 25-120°C at 10 K/min, 2 ^nd run 25-150°C at 10 K/min) as known in the art and described e.g. in ISO11-359-2.

The resin compositions according to the present invention may further comprise a catalyst.

Suitable catalysts include alkali metal hydroxides such as sodium or potassium hydroxide; alkali metal alkoxides such as sodium or potassium methoxide, or sodium or potassium ethoxide; quaternary ammonium compounds such as tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, tetrabutylammonium carbonate; tertiary amines such as diazabicyclooctane (DABCO); guanidines such as N,N,N',N'-tetramethylguanidine; amidines such as 1 ,8-diazabicyclo[5.4.0]undec-7-en and 1 ,5-diazabicyclo [4.3.0.]non-5-en; silicates such as sodium silicate; metal oxides such as calcium oxide; phosphine catalysts such as tricyclohexylphosphine, tricyclopentylphosphine, tri-n-hexylphosphine, tris(2,4,4- trimethylpentyl)phosphine, tris(2-ethylhexyl)phosphine, tri-n-octylphosphine, tri-n-decylphosphine, tri-n-dodecylphosphine, tristearylphosphine and triphenylphosphine; and combinations thereof.

In one embodiment, the catalyst is N,N,N',N'-tetramethylguanidine.

The catalyst can be comprised in the resin composition in an amount of from 0.1 wt.-% to 3 wt.-% based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, the at least one primary amine, and the at least one catalyst.

If present, the catalyst is preferably comprised in component (b) in the kit-of-parts.

In one embodiment, the resin composition comprises

(i) from 20 wt.-% to 40 wt.-% of at least one compound comprising at least two CH-acidic methylene groups,

(ii) from 45 wt.-% to 65 wt.-% of at least one compound comprising at least two a,p- unsaturated carbonyl groups,

(iii) from 5 wt.-% to 25 wt.-% of at least one primary amine, preferably isophorone diamine (IPDA), m-Xylylenediamine (MXDA), or a combination thereof, and

(iv) from 0.1 wt.-% to 3 wt.-% of at least one catalyst; each based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p- unsaturated carbonyl groups, the at least one primary amine, and the at least one catalyst.

In one embodiment, the resin composition comprises

(i) from 20 wt.-% to 40 wt.-% of trimethylolpropane triacetoacetate,

(ii) from 45 wt.-% to 65 wt.-% of trimethylolpropane triacrylate,

(iii) from 5 wt.-% to 25 wt.-% of at least one primary amine, preferably isophorone diamine (IPDA), m-Xylylenediamine (MXDA), or a combination thereof, and (iv) from 0.1 wt.-% to 3 wt.-% N,N,N',N'-tetramethylguanidine; each based on the combined weight of constituents (i) to (iv).

The resin compositions of the present invention can suitably be used for producing composite materials or as adhesive.

Accordingly, a further aspect of the present invention pertains to the use of the resin compositions or the kits-of-parts of the present invention for the production of composite materials or as adhesive.

A further aspect of the present invention pertains to a composite material, such as a component, a hybrid component, or a structural component comprising the resin compositions of the present invention.

Exemplary composite materials include, fiber- re info reed plastics such as glassfiber-reinforced plastics (GFRP), carbonfiber-reinforced plastics (CFRP), aramid fibre reinforced plastics (including Kevlar®), basalt fibre reinforced plastics and natural fibre (such as flax, hemp, jute) reinforced plastics.

In one embodiment, the composite material has a glass-transition temperature Tg of at least 110°C as determined by differential scanning calorimetry (DSC) (25-160°C at 20 K/min) after curing such as at about 160°C for at least 1 h such as for at least 1 .5 h e.g. for 1 h 40 min.

In one embodiment, the composite material has a glass-transition temperature Tg of at least 110°C as determined by thermomechanical analysis (TMA) after curing, e.g. at a temperature of about 120°C for at least 4 h such as 12 h.

The present invention is further described by the following embodiments:

1 . A resin composition comprising

(i) at least one compound comprising at least two CH-acidic methylene groups,

(ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups, and

(iii) at least one primary amine; wherein the at least one primary amine is comprised in the resin composition in an amount of at least 5 wt.-% based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p- unsaturated carbonyl groups, and the at least one primary amine. The resin composition according to item 1 , wherein the at least one primary amine is comprised in the resin composition in an amount of at least 6 wt.-%, such as at least 7 wt.-%, at least 8 wt.-%, at least 9 wt.-%, or at least 10 wt.-%, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine. A resin composition comprising

(i) at least one compound comprising at least two CH-acidic methylene groups,

(ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups, and

(iii) at least one primary amine; wherein the amine molar ratio (AMR) of the at least one primary amine to the at least one compound comprising at least two CH-acidic methylene groups and the at least one compound comprising at least two a,p-unsaturated carbonyl groups is at least 10% as calculated by the following formula: reactive amine protons [mol] reactive amine protons [mol] + a, unsaturated carbonyl groups [mol] + methylene protons of CH acidic methylene groups [mol] The resin composition according to item 3, wherein the amine molar ratio (AMR) is at least 12%, preferably at least 14%, and more preferably at least 16%. The resin composition according to any one of items 1 to 4, wherein the at least one primary amine is selected from aliphatic amines, cycloaliphatic amines, cycloaromatic amines, and combinations thereof. The resin composition according to item 5, wherein the cycloaliphatic amine is selected from the group consisting of isophorone diamine (IPDA), 1 ,2-diaminocyclohexane, 1 ,3- diaminocyclohexane, 1 ,4-diaminocyclohexane, 4-methylcyclohexane-1 ,3-diamine, 4- methylcyclohexane-1 ,2-diamine, 2-methylcyclohexane-1 ,3-diamine, 3-methylcyclohexane-1 ,2- diamine, 1 ,3-bis(aminomethyl)cyclohexane, 1 ,3-cyclopentanediamine, 4,4'- methylenebis(cyclohexaneamine), 4,4'-methylenebis(2-methylcyclohexaneamine), 4,4'- methylenebis(2-ethylcyclohexaneamine), 4,4'-methylenebis(2,6-dimethylcyclohexaneamine), 4,4'-methylenebis(2,6-diethylcyclohexaneamine), 4,4'-methylenebis(2,6-diisopropyl- cyclohexaneamine), 4,4'-methylenebis(2-methyl-6-isopropyl-cyclohexaneamine), 4,4'- methylenebis(2-ethyl-6-methyl-cyclohexaneamine), 4,4'-methylenebis(2-chloro- cyclohexaneamine), 2,4-diethyl-6-methyl-1 ,3-cyclohexanediamine, 4,6-diethyl-2-methyl-1 ,3- cyclohexanediamine, and combinations thereof, preferably wherein the cycloaliphatic amine is isophorone diamine (IPDA). The resin composition according to item 5, wherein the cycloaromatic amine is selected from the group consisting of m-Xylylenediamine (MXDA), 1 ,2-diaminobenzene, 1 ,3- diaminobenzene, 1 ,4-diaminobenzene, 4-methyl-1 ,3-phenylenediamine, 4-methyl-1 ,2- phenylenediamine, 2-methyl-1 ,3-phenylenediamine, 3-methyl-1 ,2-phenylenediamine, 4,4'- methylenedianiline, 4,4'-methylenebis(2-methylaniline), 4,4'-methylenebis(2-ethylaniline), 4,4'- methylenebis(2,6-dimethylaniline), 4,4'-methylenebis(2,6-diethylaniline), 4,4'-methylenebis(2,6- diisopropylaniline), 4,4'-methylenebis(2-methyl-6-isopropylaniline), 4,4'-methylenebis(2-ethyl-6- methyl-aniline), 4,4'-methylenebis(2-chloroaniline), 3,5-diethyltoluene-2,4-diamine, 3,5- diethyltoluene-2,6-diamine, and combinations thereof, preferably wherein the cycloaromatic amine is m-Xylylenediamine (MXDA). The resin composition according to any one of items 1 to 7, wherein the at least one compound comprising at least two CH-acidic methylene groups comprises two CH-acidic methylene groups, three CH-acidic methylene groups, or four CH-acidic methylene groups, five CH-acidic methylene groups, or six CH-acidic methylene groups, preferably three CH-acidic methylene groups. The resin composition according to any one of items 1 to 8, wherein the at least one compound comprising at least two CH-acidic methylene groups is selected from a compound comprising two 2-methylene-1 ,3-dicarbonyl groups, a compound comprising three 2-methylene-1 ,3- dicarbonyl groups, a compound comprising four 2-methylene-1 ,3-dicarbonyl groups, a compound comprising five 2-methylene-1 ,3-dicarbonyl groups, a compound comprising six 2- methylene-1 ,3-dicarbonyl groups, or combinations thereof, preferably a compound comprising three 2-methylene-1 ,3-dicarbonyl groups. The resin composition according to any one of items 1 to 9, wherein the at least one compound comprising at least two CH-acidic methylene groups is selected from the group consisting of

1 ,4-butanediol diacetoacetate, 1 ,6-hexanediol diacetoacetate, neopentylglycol diacetoacetate, cyclohexane dimethanol diacetoaceta, 2-ethyl-2-butyl-1 ,3-propanediol diacetoacetate, cyclohexanedimethanol diacetoacetate, trimethylolpropane triacetoacetate, glycerol triacetoacetate, polycaprolactone triacetoacetate, ethoxylated or propoxylated trimethylol propane triacetoacetate, ethoxylated or propoxylated glycerol triacetoacetate, pentaerythritol tetraacetoacetate, ethoxylated or propoxylated pentaerythritol tetraacetoacetate, ditrimethylolpropane tetraacetoacetate, dipentaerythritol hexaacetoacetate, and combinations thereof, preferably wherein the at least one compound comprising at least two CH-acidic methylene groups is trimethylolpropane triacetoacetate.

11 . The resin composition according to any one of items 1 to 10, wherein the resin composition comprises from 20 wt.-% to 40 wt.-%, preferably from 30 wt.-% to 36 wt.-%, of the at least one compound comprising at least two CH-acidic methylene groups, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine.

12. The resin composition according to any one of items 1 to 11 , wherein the at least one compound comprising at least two a,p-unsaturated carbonyl groups comprises two a,p- unsaturated carbonyl groups, three a,p-unsaturated carbonyl groups, or four a.p-unsaturated carbonyl groups, preferably three a,p-unsaturated carbonyl groups.

13. The resin composition according to any one of items 1 to 12, wherein the at least one compound comprising at least two a,p-unsaturated carbonyl groups is a diacrylate, a triacrylate, a tetraacrylate, or a combinations thereof.

14. The resin composition according to any one of items 1 to 13, wherein the at least one at least one compound comprising at least two a,p-unsaturated carbonyl groups is selected from the group consisting of ethanediol diacrylate, 1 ,3-propanediol diacrylate, 1 ,4-butanediol acrylate, poly(butanediol)diacrylate, polybutadiene diacrylate, 3-methyl-1 ,5-pentanediol diacrylate, 1 ,6- hexanediol diacrylate, ethylene or propylene glycol diacrylate, diethylene or dipropylene glycol diacrylate, triethylene or tripropylene glycol diacrylate, tertraethylene or tetrapropylene glycol diacrylate, polyethylene or polypropylene glycol diacrylate, resorcinol diglycidyl ether diacrylate, neopentyl glycol diacrylate, cyclohexane dimethanol diacrylate, ethoxylated or propoxylated neopentyl glycol diacrylate, ethoxylated or propoxylated cyclohexanedimethanol diacrylate, acrylated epoxy diacrylate, aryl and aliphatic urethane diacrylate .polyester diacrylate, trimethylolpropane triacrylate, glycerol triacrylate, ethoxylated or propoxylated trimethylolpropane triacrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, ethoxylated or propoxylated glycerol triacrylate, pentaerythritol triacrylate, aryl and aliphatic urethane triacrylates, melamine triacrylates, epoxy novolac triacrylates, pentaerythritol tetraccrylate, ethoxylated or propoxylated pentaerythritol tetraacrylate, dipentaerythritol tetraacrylate, ethoxylated or propoxylated dipentaerythritol tetraacrylate, aryl and aliphatic urethane tetraacrylates, melamine tetraacrylates, epoxy novolac tetraacrylates, and combinations thereof, preferably wherein the at least one at least one compound comprising at least two a,p- unsaturated carbonyl groups is trimethylolpropane triacrylate. The resin composition according to any one of items 1 to 14, wherein the resin composition comprises from 45 wt.-% to 65 wt.-%, preferably from 50 wt.-% to 60 wt.-%, of the at least one compound comprising at least two a,p-unsaturated carbonyl groups, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine. The resin composition according to any one of items 1 to 15, wherein the resin composition comprises from 5 wt.-% to 25 wt.-% of isophorone diamine (IPDA), m-Xylylenediamine (MXDA), or a combination thereof, based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine. The resin composition according to any one of items 1 to 16, wherein the resin composition further comprises a catalyst, preferably wherein the catalyst is N,N,N',N'-tetramethylguanidine. The resin composition according to any one of items 1 to 17, wherein the resin composition comprises

(i) from 20 wt.-% to 40 wt.-% of at least one compound comprising at least two CH-acidic methylene groups,

(ii) from 45 wt.-% to 65 wt.-% of at least one compound comprising at least two a,p- unsaturated carbonyl groups, and

(iii) from 5 wt.-% to 25 wt.-% of at least one primary amine, preferably isophorone diamine (IPDA), m-Xylylenediamine (MXDA), or a combination thereof; based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p-unsaturated carbonyl groups, and the at least one primary amine. The resin composition according to any one of items 1 to 18, wherein the resin composition has a glass-transition temperature Tg of at least 110°C as determined by differential scanning calorimetry (DSC) after curing at a temperature of about 160°C for at least 1 h. A kit-of-parts comprising component (a) and component (b), wherein component (a) and component (b) are arranged in such a way that the components do not come into contact with each other, and wherein component (a) comprises

(i) at least one compound comprising at least two CH-acidic methylene groups, and

(ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups; and component (b) comprises

(iii) at least one primary amine; wherein the at least one primary amine is comprised in the kit-of-parts in an amount of at least 5 wt.-% based on the combined weight of the at least one compound comprising at least two CH-acidic methylene groups, the at least one compound comprising at least two a,p- unsaturated carbonyl groups, and the at least one primary amine. A kit-of-parts comprising component (a) and component (b), wherein component (a) and component (b) are arranged in such a way that the components do not come into contact with each other, and wherein component (a) comprises

(i) at least one compound comprising at least two CH-acidic methylene groups, and

(ii) at least one compound comprising at least two a,p-unsaturated carbonyl groups; and component (b) comprises

(iii) at least one primary amine; wherein the amine molar ratio (AMR) of the at least one primary amine to the at least one compound comprising at least two CH-acidic methylene groups and the at least one compound comprising at least two a,p-unsaturated carbonyl groups is at least 10% as calculated by the following formula: reactive amine protons [mol] reactive amine protons [mol] + a, p unsaturated carbonyl groups [mol] + methylene protons of CH acidic methylene groups [mol]

22. Use of the resin composition according to any one of items 1 to 19 or the kit-of-parts according to item 20 or 21 for the production of composite materials or as adhesive.

23. A composite material, such as a component, a hybrid component, or a structural component, comprising the resin composition according to any one of items 1 to 19.

24. The composite material according to item 23, wherein the composite material has a glasstransition temperature Tg of at least 110°C as determined by differential scanning calorimetry (DSC) after curing at a temperature of about 160°C for at least 1 h.

It will be obvious for a person skilled in the art that these embodiments and items only depict examples of a plurality of possibilities. Hence, the embodiments shown here should not be understood to form a limitation of these features and configurations. Any possible combination and configuration of the described features can be chosen according to the scope of the invention. All embodiments and preferred embodiments described herein in connection with one particular aspect of the invention shall likewise apply to all other aspects of the present inventions such as uses or methods according to the present invention.

The present invention will be further illustrated by the following examples, which should not be construed as limiting the present invention.

Examples

Abbreviations

DSC: Differential Scanning Calorimetry

RT: Room temperature

Tg: Glass transition temperature Materials

Example 1

Component A was prepared by mixing at room temperature TMPTAcAc with TMPTA for one minute until complete homogenisation. Component B was prepared by mixing at room temperature TMG with IPDA for one minute until complete homogenisation.

The two components A and B were then mixed at room temperature for one minute until complete homogenisation. The mixture was casted into an aluminum pan with diameter of 5 cm containing 6 g of the resin system. The resin system was cured according to the following cure and post-cure cycles:

Cure and post-cure cycles applied:

Cured for 7 days at room temperature and then demoulded from the aluminium pan. Post cure applied, holding 1 h 40 min at about 160°C and then cooled to RT.

The cured material had the following dimensions: diameter = 5 cm, thickness = 2 mm.

The components and their amounts in gram (g) and wt.-% (% based on the total weight of the mixture) are given in Table 1 (g) and Table 2 (wt.-%).

Reference Example 2

TMG was first mixed at RT with TMPTA for one minute until complete homogenisation. The mixture of TMG and TMPTA was further mixed at RT with TMPTAcAc for one minute until complete homogenisation. The mixture was casted into an aluminum pan with diameter of 5 cm containing 6 g of the resin system. The resin system was cured according to the following cure cycle:

Cure and post-cure cycles applied:

Cured for 7 days at room temperature and then demoulded from the aluminium pan. Post cure applied, holding 1 h 40 min at about 160°C and then cooled to RT.

The cured material had the following dimensions: diameter = 5 cm, thickness = 2 mm

The components and their amounts in gram (g) and wt.-% (% based on the total weight of the mixture) are given in Table 1 (g) and Table 2 (wt.-%).

Reference Example 3

Component A was prepared by mixing at RT TMPTAcAc with TMPTA for one minute until complete homogenisation. Component B was prepared by mixing at RT TMG with IPDA for one minute until complete homogenisation.

The two components A and B were then mixed at RT for one minute until complete homogenisation. The mixture was casted into an aluminum pan with diameter of 5 cm containing 6 g of the resin system. The resin system was cured according to the following cure and post-cure cycles:

Cure and post-cure cycles applied:

Cured for 7 days at room temperature and then demoulded from the aluminium pan. Post cure applied, holding 1 h 40 min at about 160°C and then cooled to RT.

The cured material had the following dimensions: diameter = 5 cm, thickness = 2 mm

The components and their amounts in gram (g) and wt.-% (% based on the total weight of the mixture) are given in Table 1 (g) and Table 2 (wt.-%).

Table 1 : Overview of compositions (amounts in grams)

Table 2: Overview of compositions (amounts in wt.-% based on the total weight of the mixture)

Experimental procedure for testing of cured materials Samples of the cured compositions were cut to small specimens and the glass transition temperature (Tg) was analysed by Differential Scanning Calorimetry (DSC) using a Metler Toledo Instrument DSC3. The cured samples were cut into small pieces with a wire cutter and placed in a 40pL aluminium crucible. The test method applied one heating ramp (heat-up: 25-160 °C at 20 K/min). The Tg midpoint was evaluated and the result are given in Table 3. Table 3: Glass transition temperature

As can be taken from Table 3, the resin composition of Example 1 according to the present invention exhibited a significantly higher Tg compared to the sample with no IPDA (Ref. Ex. 2) and the sample with lower amounts of IPDA (Ref. Ex. 3). Example 4

Component A was prepared by mixing at RT TMPTAcAc with TMPTA for one minute until complete homogenisation.

Component B was prepared by mixing at RT TMG with IPDA for one minute until complete homogenisation. The two components A and B were then mixed at room temperature for one minute until complete homogenisation. The mixture was casted into an aluminum pan with diameter of 5 cm containing 6 g of the resin system.

The components and their amounts in gram (g) and wt.-% (% based on the total weight of the mixture) are given in Table 4 (g) and Table 5 (wt.-%). Table 4: Overview of compositions (amounts in grams) Table 5: Overview of compositions (amounts in wt.-% based on the total weight of the mixture)

The resin systems of Ex. 4a (ref.), Ex. 4b, Ex. 4c (ref.) and Ex. 4d were cured according to the cure and post-cure cycles shown in Table 6. The glass-transition temperature (Tg) of the cured compositions Ex. 4a (ref.), Ex. 4b, Ex. 4c (ref.) and Ex. 4d was determined using thermomechanical analysis (TMA) as follows. The machine used was a Mettler Toledo instrument TMA SDTA840. The sample dimensions were 6x6 mm2 (length x width) and 2.0 mm thickness. The test method applied two heating ramps (1 ^st heat-up: 25-120 °C at 10 K/min, 2 ^nd heat-up: 25-150 °C at 10 K/min). The Tg was evaluated on the second ramp. The results are given in Table 6.

Table 6: Curing conditions and Tg (TMA) results

As can be taken from Table 6, the resin composition of Examples 4b and 4d according to the present invention exhibited a significantly higher Tg compared to the samples with lower amounts of I PDA (Ex. 4a (ref.) and Ex. 4c (ref.)).