Oxetane-based compounds

Abstract

The present invention relates to oxetane-based compounds, a method of manufacturing oxetane-based compounds, and to applications of the same.

Description

[0001] OXETANE-BASED COMPOUNDS

[0002] Background

[0003] The present invention relates to oxetane-based compounds, a method of manufacturing oxetane- based compounds, and to applications of the same.

[0004] Molecules having epoxy functionalities are of great interest for crosslinking applications such as for 3D-printing, coating, adhesive, composite and construction industry. However, said molecules are often manufactured via epichlorhydrine, which however is hazardous and should be avoided.

[0005] Alternatively, molecules having oxetane functionalities are of great interest for crosslinking applications. The research on suitable molecules is limited, so far.

[0006] Many of the current composite and building and construction materials based on oxetanes have limitations or disadvantages that restrict their use as e.g. thermosetting resins in high-temperature applications and use of easy processing.

[0007] Against this background, there is a need for specific oxetane-based compounds, as well as efficient processes towards respective molecules in order to provide suitable crosslinking molecules allowing the manufacturing of coatings, composite and building and construction materials having good properties such as high mechanical resistance.

[0008] It is an object of the present invention to provide oxetane-based compounds that are suitably for e.g. crosslinking. It is a further object of the present invention to provide compounds and compositions suitable for cationic resin applications. It is a further object of the present invention to provide compounds having good compatibility with compounds / resins, e.g. with epoxy compounds.

[0009] It is a further object of the present invention to provide compositions suitable for 3D-printing, chemical anchoring, or electronic encapsulation or for the manufacturing coatings, paints, EMC materials, adhesives, sealants, composite or building and construction materials. It is a further object of the present invention to provide a safe and / or efficient method of manufacturing said oxetane-based compounds. Summary

[0010] In a first aspect, the present invention relates to a compound of formula (1) wherein

[0011] RAis H or C1-C10-alkyl;

[0012] RBis H or C1-C10-alkyl;

[0013] Rcis H or C1-C10-alkyl;

[0014] RDis H, C1-C1 O-alkyl, or C1-C10-acyl;

[0015] X is 0 or NRN;

[0016] B is C1-C40-alkylene, (C1-C20-alkoxylene)r,s,t-(C1-C20-alkylene)-C1-C20-alkoxylene, (C1- C10-alkylene)r,s,t-(carbocyclic group having between 4 and 20 carbon atoms)-(C1-C10-alkylene)r,s,t, (C1-C10-alkylene)r,s,t-(heterocyclic group having between 4 and 20 ring members)-(C1-C10- alkylene)r.s,t, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 4 and 10 carbon atoms)-C1- C6-alkylene-(carbocyclic group having between 4 and 10 carbon atoms)-(C1-C6-alkylene)r,s,t, alkoxylene-(carbocyclic group having between 4 and 10 carbon atoms)-C1-C6-alkylene-(carbocyclic group having between 4 and 10 carbon atoms)-alkoxylene, or paraffin-derived alkylene, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx, optionally wherein each CH2 group in the aforementioned groups is independently replaced by one or more same or different RY; m is 0 or 1 ; n is 0 or 1 ; o is at least 2;

[0017] RNis H or C1-C5-alkyl; r, s, t are independently 0 or 1 ; Rxis C1-C6-alkyl, halogen, OH, carboxy, amino, or phenyl; and

[0018] RYis -O- or C=O.

[0019] In a second aspect, the present invention relates to a method of manufacturing an oxetane- containing compound, the method comprising the step of reacting a compound comprising at least one functional group selected from the group consisting of isocyanate, chloride, a,p-unsaturated carbonyl, and combinations thereof (C-B), with a compound of formula (10) wherein

[0020] RAis H or C1-C10-alkyl;

[0021] RMis C1-C10-alkyl.

[0022] In a third aspect, the present invention relates to an oxetane-containing compound obtained by a method according to the second aspect (including all embodiments).

[0023] In a fourth aspect, the present invention relates to a composition comprising a compound according to the first aspect (including all embodiments) or the third aspect (including all embodiments) and an additive (A) selected from the group consisting of catalyst, reinforcement fibres, a filler, compounds comprising at least one a,p-unsaturated carbonyl group, epoxies, vinyl and allyl compounds, oxetanes, amines, isocyanates, cyanate esters, and combinations thereof.

[0024] In a fifth aspect, the present invention relates to a process of manufacturing a 3D-printed object, a coating, a paint, an EMC material, an adhesive, a sealant, a composite or building and construction material comprising the steps of i) contacting a composition comprising a compound according to the first aspect (including all embodiments) or the third aspect (including all embodiments) with an additive (A) selected from the group consisting of catalyst, reinforcement fibres, a filler, compounds comprising at least one a,p- unsaturated carbonyl group, epoxies, vinyl and allyl compounds, oxetanes, amines, isocyanates, cyanate esters, and combinations thereof to provide a mixture (M); and ii) curing said mixture (M). In a sixth aspect, the present invention relates to a 3D-printed object, a coating, a paint, an EMC material, an adhesive, a sealant, a composite or building and construction material obtainable by a process according to the fifth aspect (including all embodiments).

[0025] In a seventh aspect, the present invention relates to the use of a compound according to the first aspect (including all embodiments) or the third aspect (including all embodiments) or a composition according to the fourth aspect (including all embodiments) for use in 3D-printing, chemical anchoring, or in electronic encapsulation or for manufacturing a coating, a paint, an EMC material, an adhesive, a sealant, a composite or building and construction material.

[0026] In an eighth aspect, the present invention relates to a method for fastening anchoring elements in boreholes, wherein a composition according to the fourth aspect (including all embodiments) is placed in the boreholes and the anchoring element is inserted therein.

[0027] It has surprisingly been found that the inventive compounds and processes solve at least one of the above objects and that the present invention provides inter alia an efficient and / or safe method of manufacturing oxetane-based compounds, compositions comprising said molecules and / or 3D- printed objects, EMC materials, adhesives, sealants, coatings, paints, composites and building and construction materials having suitable properties.

[0028] Detailed Description

[0029] In the following, the invention will be explained in more detail.

[0030] The term “alkyl” as used herein denotes in each case a straight-chain or branched saturated hydrocarbon group having usually from 1 to 10 carbon atoms, preferably 1 to 6 or 1 to 4 carbon atoms, more preferably 1 to 3 or 1 to 2 or 1 carbon atoms. Examples of an alkyl group are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl, iso-butyl, tert-butyl, n-pentyl, 1 -methylbutyl, 2- methylbutyl, 3-methyl-butyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2- dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethyl-butyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1- ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1-ethyl-1 -methylpropyl, 1-ethyl- 2-methylpropyl, and the like.

[0031] The term “acyl” as used herein denotes in each case an alkyl such as a C1 -C10-alkyl, that is bonded to the remainder of the molecule via a carbonyl moiety. Examples of an acyl are acetyl (C1- acyl), propionyl (C2-acyl), butyryl (C3-acyl), and the like. The term “alkylene” as used herein refers to an at least bivalent straight-chain or branched alkyl group, e.g. -(CH2)x- or -(CH(CH3)CH2)x-, wherein x is a positive integer of usually 1 to 40, such as 1 to 20 or 1 to 5. In the context of the present invention "C1-C10-alkylene" refers to an alkylene moiety with 1 , 2, 3, 4, 5, 6, 7, 8, 9, and 10, respectively, carbon atoms, e.g. -CH2- groups; the term "alkylene", however, not only comprises straight-chain alkylene groups, i.e. "alkylene chains", but branched alkylene groups, as well. Suitably, the alkylene is bivalent, or bound to at least three moieties such as bound to 3 (also referred to a trivalent), 4 (also referred to a tetravalent), or 5 (also referred to a pentavalent) moieties.

[0032] In general, the term “at least bivalent” as used herein denotes that the respective group (such as alkylene) can be bivalent (i.e. wherein said group is bound to two moieties) or bound to at least three moieties, wherein the respective moieties are suitably in line with the compound of formula (1). Suitably, in a bivalent group of the compound of formula (1), o is 2 and in a trivalent group of the compound of formula (1), o is 3, etc..

[0033] The term “alkoxylene” as used herein refers to an at least bivalent linear or branched alkylene group which is bonded via an oxygen atom, e.g. -(CH2O)x- or (CH(CH3)CH2O)x-, wherein x is a positive integer of usually 1 to 20, preferably 1 to 10 or 1 to 5. In the context of the present invention "C1- C10- alkoxylene " refers to an alkoxylene moiety with 1 , 2, 3, 4, 5, 6, 7, 8, 9, and 10, respectively, carbon atoms that are uniformly connected via an oxygen. Thus, C1-C10-alkoxylene may denote -(CH2O)x-, wherein x is a positive integer of 1 to 10 and a C3-C12-alkoxylene may denote -(CH(CH3)CH2O)x-, wherein x is a positive integer of 1 to 4.

[0034] The term “carbocyclic group” as used herein refers to an at least bivalent cyclic group, wherein all ring members are carbon atoms. The carbocycle may be saturated, partially or fully unsaturated, or aromatic, wherein saturated means that only single bonds are present, and partially or fully unsaturated means that one or more double bonds may be present in suitable positions, while the Huckel rule for aromaticity is not fulfilled, whereas aromatic means that the Huckel (4n + 2) rule is fulfilled. A “carbocyclic group having between 4 and 20 carbon atoms” refers to an at least bivalent cyclic group having between 4 and 20 carbon atoms. An “aromatic carbocyclic group having between 4 and 20 carbon atoms” refers to an at least bivalent aromatic ring system. Said group may be fully aromatic, such as a phenylene or naphthylene, or may comprise at least two bivalent aromatic ring systems that are connected via a bond such as phenylene-phenylene. Within the meaning of the present invention, the term “carbocyclic group” encompasses monocylic, bicyclic, and tricyclic ring systems.

[0035] A “heterocyclic group having between 4 and 20 ring members” refers to an at least bivalent heterocyclic group having between 4 and 20 ring members. The ring members are selected from carbon atoms and heteroatoms, wherein at least one, such as 1 , 2, 3, or 4, of the ring members is a heteroatom. Suitably heteroatom are selected from N, O, and S, wherein S may be present as S, SO, or SO2. The remaining ring members are carbon atoms. The heterocycle may be saturated, partially or fully unsaturated, or aromatic, wherein saturated means that only single bonds are present, and partially or fully unsaturated means that one or more double bonds may be present in suitable positions, while the Huckel rule for aromaticity is not fulfilled, whereas aromatic means that the Huckel (4n + 2) rule is fulfilled. An aromatic heterocyclic group having between 4 and 20 carbon atoms comprises at least one aromatic heterocyclic ring system. The group may be fully aromatic, such as a triazine, or may comprise at least two bivalent aromatic ring systems that are connected via e.g. a bond. Suitably, the heterocyclic group is bivalent, or bound to at least three moieties such as bound to 3, 4, or 5 moieties. Within the meaning of the present invention, the term “heterocyclic group” encompasses monocylic, bicyclic, and tricyclic ring systems.

[0036] The term "substituted" as used herein, means that a hydrogen atom bonded to a designated atom is replaced with a specified substituent, provided that the substitution results in a stable or chemically feasible compound. Unless otherwise indicated, a substituted atom may have one or more substituents and each substituent is independently selected.

[0037] The term "substitutable", when used in reference to a designated atom, means that attached to the atom is a hydrogen, which can be replaced with a suitable substituent.

[0038] When it is referred to certain atoms or moieties being substituted with "one or more" substituents, the term "one or more" is intended to cover at least one substituent, e.g. 1 to 10 substituents, preferably 1 , 2, 3, 4 or 5 substituents, more preferably 1 , 2, or 3 substituents, most preferably 1 or 2 substituents. When neither the term "unsubstituted" nor "substituted" is explicitly mentioned concerning a moiety, said moiety is to be considered as unsubstituted. The skilled person is aware that S, SO or SO2 is to be understood as follows:

[0039] It is to be understand that denotes the bond of the respective moiety to the remainder of the molecule.

[0040] The term “vinyl” as used herein can be expressed as follows:

[0041] The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group.

[0042] The term “C=O” as used herein denotes a carbonyl moiety (also known as C(O)) and can be expressed as follows:

[0043] The term “halogen” denotes in each case fluorine, bromine, chlorine, or iodine, in particular chlorine and fluorine.

[0044] The terms “about” in the context of the present invention denotes an interval of accuracy that a person skilled in the art will understand to still ensure the technical effect of the feature in question. The term typically indicates a deviation from the indicated numerical value of ±10%, preferably ±5%, more preferably ±2%, and in particular ±1%.

[0045] It needs to be understood that the term “comprising” is not limiting. For the purposes of the present invention, the term “consisting of’ is considered to be a preferred embodiment of the term “comprising of’. If hereinafter a group is defined to comprise at least a certain number of embodiments, this is also meant to encompass a group which preferably consists of these embodiments only. As aforementioned, the present invention relates in a first aspect to a compound of formula (1) wherein

[0046] RAis H or C1-C10-alkyl;

[0047] RBis H or C1-C10-alkyl;

[0048] Rcis H or C1-C10-alkyl;

[0049] RDis H, C1-C10-alkyl, or C1-C10-acyl;

[0050] X is O or NRN;

[0051] B is C1-C40-alkylene, (C1-C20-alkoxylene)r,s,t-(C1-C20-alkylene)-C1-C20-alkoxylene, (C1- C10-alkylene)r,s,t-(carbocyclic group having between 4 and 20 carbon atoms)-(C1-C10-alkylene)r,s,t, (C1-C10-alkylene)r,s,t-(heterocyclic group having between 4 and 20 ring members)-(C1-C10- alkylene)r.s,t, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 4 and 10 carbon atoms)-C1- C6-alkylene-(carbocyclic group having between 4 and 10 carbon atoms)-(C1-C6-alkylene)r,s,t, alkoxylene-(carbocyclic group having between 4 and 10 carbon atoms)-C1-C6-alkylene-(carbocyclic group having between 4 and 10 carbon atoms)-alkoxylene, or paraffin-derived alkylene, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx, optionally wherein each CH2 group in the aforementioned groups is independently replaced by one or more same or different RY; m is 0 or 1 ; n is 0 or 1 ; o is at least 2;

[0052] RNis H or C1-C5-alkyl; r, s, t are independently 0 or 1 ;

[0053] Rxis C1-C6-alkyl, halogen, OH, carboxy, amino, or phenyl; and RYis -O- or C=O. The inventive compounds provide molecules having oxetane functionalities allowing suitable crosslinking properties and the convenient accessibility of new 3D-Printing, EMC materials, coatings, paints, adhesives, sealants, composite or building and construction materials. Further, the inventive compounds provide good chelating properties to metal such as copper in e.g. electronic application.

[0054] In particular, particular embodiments of the present invention comprise 1 ,3-diketone compounds. Without wishing to be bound by theory, the present inventors have found that such compounds provide numerous addition and performance benefits. For example, inventive compounds containing 1 ,3-diketone compounds have been found to demonstrate improved chelating abilities, crosslinking properties, temperature resistance, and the like.

[0055] In the following, particular embodiments of the present invention such as moieties are described in further details. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments.

[0056] In one embodiment, RAis H or C1-C8-alkyl, preferably H or C1-C6-alkyl, more preferably H or C1- C4-alkyl, still more preferably H or C1-C3-alkyl, even more preferably H, methyl, or ethyl, and in particular ethyl.

[0057] In one embodiment, RBis H or C1-C8-alkyl, preferably H or C1-C6-alkyl, more preferably H or C1- C4-alkyl, still more preferably H or C1-C3-alkyl, and in particular H or methyl.

[0058] In one embodiment, Rcis H or C1-C8-alkyl, preferably H or C1-C6-alkyl, more preferably H or C1- C4-alkyl, still more preferably H or C1-C3-alkyl, and in particular H or methyl.

[0059] In one embodiment, RDis H, C1-C8-alkyl, or C1-C8-acyl, preferably H, C1-C6-alkyl, or C1-C6-acyl, more preferably H, C1-C4-alkyl, or C1-C4-acyl, still more preferably H, C1-C3-alkyl, or C1-C3-acyl, and in particular H, methyl, or acetyl.

[0060] In one embodiment, RDis H or C1-C8-acyl, preferably H or C1-C6-acyl, more preferably H or C1- C4-acyl, still more preferably H or C1-C3-acyl, and in particular H, acetyl, or propionyl.

[0061] In one embodiment, RDis C1-C8-acyl, preferably C1-C6-acyl, more preferably C1-C4-acyl, still more preferably C1-C3-acyl, and in particular acetyl or propionyl.

[0062] In one embodiment, X is O, NH, or N(Me), preferably O or NH. In one embodiment, X is O. In one embodiment, X is NH. In one embodiment, the C1 -C40-alkylene is C2-C40-alkylene, or C2-C30-alkylene, or C2-C20- alkylene, or C2-C16-alkylene, or C2-C10-alkylene, or C2-C5-alkylene, or C1-C30-alkylene, or C1- C25-alkylene, or C1-C20-alkylene, or C1-C15-alkylene, or C1-C16-alkylene, or C1 -C14-alkylene, or C1-C12-alkylene, or C1-C10-alkylene, or C1-C8-alkylene, or C1-C6-alkylene, or C1-C4-alkylene, or C1-C2-alkylene.

[0063] In one embodiment, in the alkylene no CH2 group is independently replaced by one or more same or different RY. In another embodiment, in the alkylene at least one CH2 group is independently replaced by one or more same or different RY. In this connection, in the alkylene 1 to 8, preferably 1 to 6 or 1 to 4, CH2 group may be independently replaced by one or more same or different RY.

[0064] In one embodiment, the alkylene is bivalent, trivalent, tetravalent, or pentavalent, suitably bivalent, trivalent, or tetravalent.

[0065] In one embodiment, the (C1-C20-alkoxylene)r,s,t-(C1-C20-alkylene)-C1-C20-alkoxylene is (C1-C18- alkoxylene)r,s,t-(C1 -C10-alkylene)-C1 -C18-alkoxylene, or (C1 -C16-alkoxylene)r,s,t-(C1 -C10-alkylene)- C1-C16-alkoxylene, or (C1-C14-alkoxylene)r,s,t-(C1-C10-alkylene)-C1-C14-alkoxylene, or (C1-C12- alkoxylene)r,s,t-(C1 -C10-alkylene)-C1 -C12-alkoxylene, or (C1 -C10-alkoxylene)r,s,t-(C1 -C10-alkylene)- C1-C10-alkoxylene.

[0066] In one embodiment, the (C1-C10-alkylene)r,s,t-(carbocyclic group having between 4 and 20 carbon atoms)-(C1-C10-alkylene)r,s,t is (C1-C6-alkylene)r,s,t-(carbocyclic group having between 4 and 16 carbon atoms)-(C1-C6-alkylene)r,s,t, preferably (C1-C2-alkylene)r,s,t-(carbocyclic group having between 4 and 14 carbon atoms)-(C1-C2-alkylene)r,s,t, or (C1-C2-alkylene)r,s,t-(carbocyclic group having between 4 and 12 carbon atoms)-(C1-C2-alkylene)r,s,t, or (C1-C2-alkylene)r,s,t-(carbocyclic group having between 5 and 10 carbon atoms)-(C1-C2-alkylene)r,s,t, or (C1-C2-alkylene)r,s,t- (carbocyclic group having between 5 and 8 carbon atoms)-(C1-C2-alkylene)r,s,t, or (C1-C2- alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C2-alkylene)r,s,t-

[0067] In one embodiment, in the (C1-C10-alkylene)r,s,t-(carbocyclic group having between 4 and 20 carbon atoms)-(C1-C10-alkylene)r,s,t, r, s, and t are all 0 (carbocyclic group having between 4 and 20 carbon atoms). In another embodiment, r, s, and t are all 1 . In a further embodiment, at least one of r, s, and t is 1. In one embodiment, s and t are all 0 ((C1-C10-alkylene)r-(carbocyclic group having between 4 and 20 carbon atoms)-(C1-C10-alkylene)r). In one embodiment, s and t are all 0, one r is 0 and one r is 1 ((C1-C10-alkylene)-(carbocyclic group having between 4 and 20 carbon atoms) or (carbocyclic group having between 4 and 20 carbon atoms)-(C1-C10-alkylene)). In one embodiment, the (C1-C10-alkylene)r,s,t-(carbocyclic group having between 4 and 20 carbon atoms)-(C1-C10-alkylene)r,s,t is carbocyclic group having between 4 and 20 carbon atoms (i.e. r, s, and t are all 0), preferably wherein the carbocyclic group having between 4 and 20 carbon atoms is carbocyclic group having between 5 and 16 carbon atoms, or carbocyclic group having between 5 and 14 carbon atoms, or carbocyclic group having between 5 and 12 carbon atoms, or carbocyclic group having between 6 and 12 carbon atoms, or carbocyclic group having between 6 and 10 carbon atoms, or carbocyclic group having between 6 and 8 carbon atoms, or carbocyclic group having between 5 and 6 carbon atoms.

[0068] In one embodiment, the (C1-C10-alkylene)r,s,t-(carbocyclic group having between 4 and 20 carbon atoms)-(C1-C10-alkylene)r,s,t is (C1-C3-alkylene)r-(carbocyclic group having between 4 and 16 carbon atoms)-(C1-C3-alkylene)r, preferably (C1-C2-alkylene)r-(carbocyclic group having between 4 and 14 carbon atoms)-(C1-C2-alkylene)r, or (C1-C2-alkylene)r-(carbocyclic group having between 4 and 12 carbon atoms)-(C1-C2-alkylene)r, or (C1-C2-alkylene)r-(carbocyclic group having between 5 and 10 carbon atoms)-(C1-C2-alkylene)r, or (C1-C2-alkylene)r-(carbocyclic group having between 5 and 8 carbon atoms)-(C1-C2-alkylene)r, or (C1-C2-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C2-alkylene)r.

[0069] In one embodiment, the (C1-C10-alkylene)r,s,t-(carbocyclic group having between 4 and 20 carbon atoms)-(C1-C10-alkylene)r,s,t is (C1-C3-alkylene)r-(carbocyclic group having between 4 and 16 carbon atoms), preferably (C1-C2-alkylene)r-(carbocyclic group having between 4 and 14 carbon atoms), or (C1-C2-alkylene)r-(carbocyclic group having between 4 and 12 carbon atoms) or (C1-C2- alkylene)r-(carbocyclic group having between 5 and 10 carbon atoms), or (C1-C2-alkylene)r- (carbocyclic group having between 5 and 8 carbon atoms), or (C1-C2-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms).

[0070] In one embodiment, the carbocyclic group (having between 4 and 20 carbon atoms) is an aromatic carbocyclic group (having between 4 and 20 carbon atoms) such as aromatic carbocyclic group having between 5 and 12 carbon atoms. In this connection, phenylene and phenylene-phenylene may be mentioned.

[0071] In another embodiment, the carbocyclic group (having between 4 and 20 carbon atoms) is a saturated carbocyclic group (having between 4 and 20 carbon atoms). In this connection, saturated carbocyclic group having 6 carbon atoms such as cyclohexyl and may be mentioned.

[0072] In one embodiment, the (C1-C10-alkylene)r,s,t-(heterocyclic group having between 4 and 20 ring members)-(C1-C10-alkylene)r,s,t is a heterocyclic group having between 4 and 20 ring members, preferably heterocyclic group having between 4 and 16 ring members, or heterocyclic group having between 4 and 10 ring members, or heterocyclic group having between 4 and 8 ring members, or heterocyclic group having between 5 and 16 ring members, or heterocyclic group having between 5 and 14 ring members, or heterocyclic group having between 5 and 12 ring members, or heterocyclic group having between 5 and 10 ring members, or heterocyclic group having between 5 and 8 ring members, or heterocyclic group having between 5 and 6 ring members.

[0073] In one embodiment, the heterocyclic group (having between 4 and 20 ring members) is an aromatic heterocyclic group (having between 4 and 20 ring members) such as aromatic heterocyclic group having between 5 and 12 ring members or aromatic heterocyclic group having between 5 and 6 ring members. In this connection, bivalent or trivalent triazine may be mentioned.

[0074] In one embodiment, the heterocyclic group (having between 4 and 20 ring members) is a saturated heterocyclic group (having between 4 and 20 ring members) such as saturated heterocyclic group having between 5 and 12 ring members or saturated heterocyclic group having between 5 and 6 ring members.

[0075] In one embodiment, the (C1-C10-alkylene)r,s,t-(carbocyclic group having between 4 and 20 carbon atoms)-(C1-C10-alkylene)r,s,t is (C1-C8-alkylene)r,s,t-(carbocyclic group having between 5 and 14 carbon atoms)-(C1-C8-alkylene)r,s,t, or C1-C6-alkylene-(carbocyclic group having between 5 and 14 carbon atoms)-C1-C6-alkylene, or C1-C2-alkylene-(carbocyclic group having between 6 and 12 carbon atoms)-C1-C2-alkylene. In one embodiment, the carbocyclic group is an aromatic mentioned.

[0076] In one embodiment, the (C1-C10-alkylene)r,s,t-(heterocyclic group having between 4 and 20 ring members)-(C1-C10-alkylene)r,s,t is (C1-C8-alkylene)r,s,t-(heterocyclic group having between 5 and 14 ring members)-(C1-C8-alkylene)r,s,t, or (C1-C6-alkylene)r,s,t-(heterocyclic group having between 4 and 10 ring members)-(C1-C6-alkylene)r,s,t, or (C1-C3-alkylene)r,s,t-(heterocyclic group having between 5 and 6 ring members)-(C1-C3-alkylene)r,s,t. In one embodiment, r, s, and t of the (C1-C10-alkylene)r,s,t-(heterocyclic group having between 4 and 20 ring members)-(C1-C10-alkylene)r,s,t are all 0 (heterocyclic group having between 4 and 20 ring members). In another embodiment, r, s, and t are all 1 . In a further embodiment, at least one of r, s, and t is 1 . In one embodiment, s and t are all 0.

[0077] In one embodiment, the heterocyclic group is a saturated heterocyclic group. In this connection, may be mentioned.

[0078] In one embodiment, the alkoxylene-(carbocyclic group having between 4 and 10 carbon atoms)-C1- C6-alkylene-(carbocyclic group having between 4 and 10 carbon atoms)-alkoxylene is alkoxylene- (carbocyclic group having between 5 and 8 carbon atoms)-C1-C5-alkylene-(carbocyclic group having between 5 and 8 carbon atoms)-alkoxylene, or alkoxylene-(carbocyclic group having between 5 and 6 carbon atoms)-C2-C4-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-alkoxylene. In one embodiment, the carbocyclic group is an aromatic carbocyclic group. In this connection, , wherein a+b = between about 3 and about 30, such as about 3, about 4, about 10, or about 30, may be mentioned.

[0079] The person skilled in the art is aware of the term “paraffin” and that it suitably refers to a mixture of saturated hydrocarbon molecules containing between 15 and 50 such as between 20 and 40 carbon atoms. In the context of the present invention, the term “paraffin-derived alkylene" denotes a mixtures of saturated hydrocarbon molecules containing suitably between 15 and 50 such as between 20 and 40 carbon atoms, wherein each hydrocarbon is at least bivalent, i.e. bound to at least two moieties. The term “chlorinated paraffin” denotes a paraffin, wherein at least two substitutable carbon atoms are substituted with chlorine. The chlorination degree of chlorinated paraffin can vary between 30 and 70 wt%. In some embodiments, the chlorinated paraffin backbone is the compound (C-B).

[0080] In one embodiment, m is 0. In another embodiment, m is 1 .

[0081] In one embodiment, n is 0. In another embodiment, n is 1 .

[0082] In one embodiment, m and n are 1 . In another embodiment, m and n are 0.

[0083] In one embodiment, o is at least 3, or at least 4, or at least 5, or at least 6, or at least 8, or at least 10, or at least. 15, or at least 20. In one embodiment, o is 2 to 30, or 2 to 25, or 2 to 20, or 2 to 15, or 2 to 10, or 2 to 8, or 2 to 6, or 2 to 5, or 2 to 4.

[0084] In one embodiment, o is 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0085] In one embodiment, o is 2, 3, 4, or 5.

[0086] In one embodiment, r is 0. In a preferred embodiment, r is 1 .

[0087] In one embodiment, s is 0. In another embodiment, s is 1 .

[0088] In one embodiment, t is 0. In another embodiment, t is 1 .

[0089] In one embodiment, at least one of r, s, or t is 1 .

[0090] In one embodiment, s and t are 0. In another embodiment, s is 1 and t is 0. In another embodiment, s and t are 1 .

[0091] In one embodiment, r, s, and t are the same.

[0092] In one embodiment, r and s are 1 and the groups of r and s are the same. In another embodiment, r and s are 1 and the groups of r and s are the different.

[0093] In one embodiment, r, s, and t are 1 and the groups of r, s, and t are the same. In another embodiment, r, s, and t are 1 and the groups of r, s, and t are different.

[0094] In one embodiment, RNis H or C1-C4-alkyl, preferably H or C1-C3-alkyl, more preferably H or methyl, and in particular H.

[0095] In one embodiment, Rxis C1-C5-alkyl, halogen, OH, carboxy, amino, or phenyl, or is C1-C4-alkyl, F, Cl, OH, carboxy, amino, or phenyl, or is C1-C3-alkyl, F, Cl, OH, or phenyl, or is C1-C2-alkyl, F, or phenyl, or is methyl.

[0096] In one embodiment, RYis -O-. In another embodiment RYis C=O. For example, an alkylene, wherein one CH2 group is replaced by -O- and one CH2 group is replaced by C=O may be expressed as follows: In this connection, four substitutable carbon atoms in said group may be independently substituted with Rx, e.g. methyl, which may result in a group as follows: In one embodiment, B is C1-C30-alkylene, (C1-C10-alkoxylene)r,s,t-(C1-C10-alkylene)-C1-C10- alkoxylene, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 5 and 12 carbon atoms)-(C1- C6-alkylene)r.s,t, (C1-C6-alkylene)r,s,t-(heterocyclic group having between 5 and 12 ring members)- (C1-C6-alkylene)r.s,t, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 4 and 8 carbon atoms)- C1-C6-alkylene-(carbocyclic group having between 4 and 8 carbon atoms)-(C1-C6-alkylene)r,s,t, alkoxylene-(carbocyclic group having between 5 and 6 carbon atoms)-C2-C4-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-alkoxylene, or paraffin-derived alkylene, preferably C1-C8-alkylene, (C1-C3-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)- (C1-C3-alkylene)r.s,t, (C1-C3-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms)- C1-C3-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3-alkylene)r, or heterocyclic group having between 5 and 6 ring members, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx; and

[0097] Rxis C1-C4-alkyl, halogen, or OH, preferably C1-C3-alkyl or F.

[0098] In one embodiment,

[0099] RAis H or C1-C4-alkyl, preferably H, methyl, or ethyl;

[0100] RBis H or C1-C4-alkyl, preferably H or methyl;

[0101] Rcis H or C1-C4-alkyl, preferably H or methyl;

[0102] RDis H or C1-C4-acyl, preferably acetyl or propionyl;

[0103] X is O or NH;

[0104] B is C1-C30-alkylene, (C1-C10-alkoxylene)r,s,t-(C1-C10-alkylene)-C1-C10-alkoxylene, (C1-C6- alkylene)r,s,t-(carbocyclic group having between 5 and 12 carbon atoms)-(C1-C6-alkylene)r,s,t, (C1- C6-alkylene)r,s,t-(heterocyclic group having between 5 and 12 ring members)-(C1-C6-alkylene)r,s,t, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C6-alkylene- (carbocyclic group having between 5 and 6 carbon atoms)-(C1-C6-alkylene)r,s,t, alkoxylene- (carbocyclic group having between 5 and 6 carbon atoms)-C2-C4-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-alkoxylene, or paraffin-derived alkylene, preferably C1-C8- alkylene, (C1-C3-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3- alkylene)r.s,t, (C1-C3-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C3- alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3-alkylene)r, or heterocyclic group having between 5 and 6 ring members, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx; and

[0105] Rxis C1-C4-alkyl, halogen, or OH, preferably C1-C3-alkyl or F. In one embodiment,

[0106] RAis H or C1-C4-alkyl, preferably H, methyl, or ethyl;

[0107] RDis H or C1-C4-acyl, preferably acetyl or propionyl;

[0108] X is O or NH;

[0109] B is C1-C10-alkylene, preferably C1-C6-alkylene, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx, m is 1 ; o is at least 2, preferably 2 to 5; and

[0110] Rxis C1 -C4-a Iky I , preferably C1 -C3-alkyl.

[0111] In one embodiment,

[0112] RAis H, methyl, or ethyl, preferably ethyl;

[0113] RBis H or C1-C4-alkyl, preferably H or methyl;

[0114] Rcis H or C1-C4-alkyl, preferably H;

[0115] RDis H or C1-C4-acyl, preferably acetyl or propionyl;

[0116] X is O;

[0117] B is C1-C10-alkylene, (C1-C3-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3-alkylene)r,s,t, (C1-C3-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C3-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3- alkylene)r, or heterocyclic group having between 5 and 6 ring members, preferably C1-C8-alkylene, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx, m is 1 ; n is 1 ; o is at least 2, preferably 2 to 5; and

[0118] Rxis C1-C4-alkyl, halogen, or OH, preferably C1-C3-alkyl or F.

[0119] In one embodiment,

[0120] RAis H, methyl, or ethyl, preferably ethyl;

[0121] RDis H or C1-C4-acyl, preferably acetyl or propionyl;

[0122] X is NH;

[0123] B is C1-C10-alkylene, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C6-alkylene)r,s,t, or (C1-C6-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C6-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C6- alkylene)r, preferably C1-C8-alkylene, (C1-C3-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3-alkylene)r,s,t, or (C1-C3-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C3-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1- C3-alkylene)r, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx; m is 1 ; n is 0; o is at least 2, preferably 2; r, s, t are independently 0 or 1 ; and

[0124] Rxis C1-C4-alkyl, or phenyl, preferably C1-C3-alkyl.

[0125] In one embodiment, the compound of formula (1) is selected from the group consisting of

[0126] In this connection, RAis preferably H, methyl, or ethyl. In one embodiment, the compound of formula (1) is selected from the group consisting of As aforementioned, the present invention relates in a second aspect to a method of manufacturing an oxetane-containing compound, the method comprising the step of reacting a compound comprising at least one functional group selected from the group consisting of isocyanate, chloride, a,p-unsaturated carbonyl, and combinations thereof (C-B), with a compound of formula (10) wherein

[0127] RAis H or C1-C10-alkyl;

[0128] RMis C1-C10-alkyl.

[0129] The inventive method provides an efficient synthetic access to oxetane-based compounds. Notable, the inventive method provides said compounds in high yield. Further, the inventive method provides an economically and environmentally friendly process due to the high atom efficiency.

[0130] Embodiments (e.g. regarding the moieties) are already above-outlined in connection with the inventive compounds and shall hold for the method, as well. In the following, embodiments of the method are described in further detail. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments.

[0131] In one embodiment, RAis H or C1-C8-alkyl, preferably H or C1-C6-alkyl, more preferably H or C1- C4-alkyl, still more preferably H or C1-C3-alkyl, and in particular H, methyl, or ethyl.

[0132] In one embodiment, RMis C1-C8-alkyl, preferably C1-C6-alkyl such as C1-C4-alkyl, or C1-C3-alkyl, or C1-C2-alkyl, preferably methyl.

[0133] In one embodiment, the compound of formula (10) is a compound of formula (10a)

[0134] (10a).

[0135] In one embodiment, the compound (C-B) comprises a backbone selected from the group consisting of C1 -C40-alkylene, (C1 -C20-alkoxylene)r,s,t-(C1 -C20-alkylene)-C1 -C20-alkoxylene, (C1-C10- alkylene)r,s,t-(carbocyclic group having between 4 and 20 carbon atoms)-(C1-C10-alkylene)r,s,t, (CICI 0-alkylene)r,s,t-(heterocyclic group having between 4 and 20 ring members)-(C1-C10-alkylene)r,s,t, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 4 and 10 carbon atoms)-C1-C6-alkylene- (carbocyclic group having between 4 and 10 carbon atoms)-(C1-C6-alkylene)r,s,t, alkoxylene- (carbocyclic group having between 4 and 10 carbon atoms)-C1-C6-alkylene-(carbocyclic group having between 4 and 10 carbon atoms)-alkoxylene, and paraffin, preferably C1-C30-alkylene, (C1- C10-alkoxylene)r,s,t-(C1-C10-alkylene)-C1-C10-alkoxylene, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 5 and 12 carbon atoms)-(C1-C6-alkylene)r,s,t, (C1-C6-alkylene)r,s,t-(heterocyclic group having between 5 and 12 ring members)-(C1-C6-alkylene)r,s,t, (C1-C6-alkylene)r,s,t- (carbocyclic group having between 5 and 6 carbon atoms)-C1-C6-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C6-alkylene)r,s,t, alkoxylene-(carbocyclic group having between 5 and 6 carbon atoms)-C2-C4-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-alkoxylene, or paraffin, more preferably C1-C8-alkylene, (C1-C3-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3-alkylene)r,s,t, (C1-C3-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C3-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3-alkylene)r, or heterocyclic group having between 5 and 6 ring members, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx, optionally wherein each CH2 group in the aforementioned groups is independently replaced by one or more same or different RY; r, s, t are independently 0 or 1 ;

[0136] Rxis C1-C6-alkyl, halogen, OH, carboxy, amino, or phenyl; and RYis -O- or C=O.

[0137] The compound (C-B) may comprise at least one carboxylic acid functionality.

[0138] A suitable compound (C-B) comprising at least one chloride functionality may e.g. be cyanuric chloride, 1-chloro-2,2-bis(chloromethyl)butane, tri-chlorethane, tetra-chlorethane, chloroform, a,a’- dichloro-xylenes (ortho, meta, para), tetrafluoro-dichloro-xylenes, 4,4'-bis(chloromethyl)-1 ,T- biphenyl (BCMB), and chlorinated paraffin.

[0139] A suitable compound (C-B) comprising at least one a,p-unsaturated carbonyl functionality may e.g. be trimethylolpropane triacrylate (TMPTA), 1 ,4-butanediol dimethacrylate, ethylene glycol dimethacrylate, and pentaerythritol tetraacrylate (PETTA).

[0140] The a,p-unsaturated carbonyl functionality is preferably an acrylate group ( o ) or a methacrylate group

[0141] Additional suitable compound (C-B) comprising at least one a,p-unsaturated carbonyl functionality are disclosed in the following table

[0142]

[0143]

[0144] A suitable compound (C-B) comprising at least one isocyanate functionality may e.g. be selected from the group consisting of

[0145] In one embodiment, compound (C-B) comprises a backbone selected from the group consisting of C1-C16-alkylene, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 5 and 12 carbon atoms)- (C1-C6-alkylene)r.s,t, (C1-C6-alkylene)r,s,t-(heterocyclic group having between 5 and 12 ring members)-(C1-C6alkylene)r,s,t, and (C1-C6-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C6-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C6- alkylene)r.s,t, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx; r, s, t are independently 0 or 1 ; and

[0146] Rxis C1-C4-alkyl, halogen, or phenyl. In one embodiment, the compound (C-B) comprises at least one chloride functionality and wherein

[0147] RAis H or C1-C4-alkyl, preferably H, methyl, or ethyl;

[0148] RMis C1-C6-alkyl, preferably methyl; preferably wherein the compound (C-B) comprises a backbone selected from the group consisting of C1-C16-alkylene, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 5 and 12 carbon atoms)-(C1-C6-alkylene)r.s,t, (C1-C6-alkylene)r,s,t-(heterocyclic group having between 5 and 12 ring members)-(C1-C6alkylene)r.s,t, and paraffin, preferably (C1-C6-alkylene)r,s,t-(aromatic heterocyclic group having between 5 and 12 ring members)-(C1-C6alkylene)r,s,t, more preferably aromatic heterocyclic group having between 5 and 12 ring members, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx; r, s, t are independently 0 or 1 ; and Rxis C1-C4-alkyl, halogen, or phenyl.

[0149] In one embodiment, the compound (C-B) comprises at least one, preferably at least two, or at least three, chloride and wherein

[0150] RAis H or C1-C4-alkyl, preferably H, methyl, or ethyl; and

[0151] RMis C1-C6-alkyl, preferably methyl; preferably wherein the compound (C-B) comprises a backbone selected from the group consisting of C1-C16-alkylene, C1-C6-alkylene-(carbocyclic group having between 5 and 12 carbon atoms)- C1-C6-alkylene, and paraffin, preferably C1-C10-alkylene, C1-C2-alkylene-(carbocyclic group having between 5 and 12 carbon atoms)-C1-C2-alkylene, and paraffin, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx; and

[0152] Rxis C1-C4-alkyl or F, preferably C1-C2-alkyl or F.

[0153] In one embodiment, the compound (C-B) comprises at least one, preferably at least two, a,p- unsaturated carbonyl and wherein

[0154] RAis H or C1-C4-alkyl, preferably H, methyl, or ethyl; and

[0155] RMis C1-C6-alkyl, preferably methyl; preferably wherein the compound (C-B) comprises a backbone selected from the group consisting of C1 -C40-alkylene, (C1 -C20-alkoxylene)r,s,t-(C1 -C20-alkylene)-C1 -C20-alkoxylene, (C1-C6- alkylene)r,s,t-(carbocyclic group having between 5 and 12 carbon atoms)-(C1-C6-alkylene)r,s,t, (C1- C6-alkylene)r,s,t-(heterocyclic group having between 4 and 10 ring members)-(C1-C6-alkylene)r,s,t, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 4 and 10 carbon atoms)-C1-C6-alkylene- (carbocyclic group having between 4 and 10 carbon atoms)-(C1-C6-alkylene)r,s,t, and alkoxylene- (carbocyclic group having between 5 and 8 carbon atoms)-C1-C5-alkylene-(carbocyclic group having between 5 and 8 carbon atoms)-alkoxylene, preferably C2-C20-alkylene, (C1-C10- alkoxylene)r,s,t-(C1 -C10-alkylene)-C1 -C10-alkoxylene, (C1 -C2-alkylene)r,s,t-(carbocyclic group having between 6 and 12 carbon atoms)-(C1-C2-alkylene)r,s,t, (C1-C3-alkylene)r,s,t-(heterocyclic group having between 5 and 6 ring members)-(C1-C3-alkylene)r,s,t, (C1-C3-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C3-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3-alkylene)r,s,t, and alkoxylene-(carbocyclic group having between 5 and 6 carbon atoms)-C2-C4-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)- alkoxylene, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx, optionally wherein each CH2 group in the aforementioned groups is independently replaced by one or more same or different RY; r, s, t are independently 0 or 1 ;

[0156] Rxis C1-C4-alkyl, or phenyl, preferably C1-C3-alkyl or phenyl; and

[0157] RYis -O- or C=O. In one embodiment, the compound (C-B) is selected from the group consisting of cyanuric chloride 1-chloro-2,2-bis(chloromethyl)butane TrimcHiylolpropanc triacry laic

[0158] 1.4 Butanediol DiMethacrylateandEthylene Glycol Dimethacrylate

[0159] Clk

[0160] In one embodiment, the compound (C-B) iscyarwicchloride

[0161] In another embodiment, the compound (B-C) is selected from the group consisting of

[0162] Trimcthylolproparin triacry lain 1 ,4-BLitanediul UiMethaciyldte , ai IU In one embodiment, the compound (B-C) further comprises at least one oxetane functionality. In one embodiment, the compound (B-C) comprises at least one a,p-unsaturated carbonyl and at least one oxetane. this connection, the compound (B-C) may be

[0163] In one embodiment, the method is conducted under basic conditions. Suitably, the method conducted in the presence of a strong base such as an alkali tert-butoxide (e.g. potassium tert- butoxide).

[0164] In one embodiment, the method is performed in the presence of a solvent. Suitably, the solvent is an optionally substituted (e.g. with an alkyl and / or halogen) hydrocarbon (such as, alkane or cyclic hydrocarbon), an alcohol, an ether, or a mixtures thereof. Examples are toluene, hexane, tetra hydrofuran, (tert-)butanol, and / or chloroform. In one embodiment, the method is performed in the presence of a catalyst such as an acid, a base, a tertiary amine, or any other suitable catalyst.

[0165] In one embodiment, the catalyst is present in the reaction from about 0.0001 to about 0.1 eq, more preferably from about 0.0002 to about 0.01 eq, even more preferably from about 0.0003 to about 0.005, and in particular from about 0.0004 to about 0.0025 eq, of the molar amount of the compound (C-B).

[0166] In general, the reaction time of said reaction is from about 1 minute to about 30 hours, preferably form about 5 minutes to about 24 hours.

[0167] In one embodiment, the reaction is done at a temperature from about -10 to about 180 °C, preferably from about 5 to about 150 °C, such as from about 10 to about 120 °C, or from about 20 to about 80 °C, or about 25 to about 50 °C.

[0168] In one embodiment, the method is conducted at elevated temperature, preferably at a temperature of about 40 to about 120 °C, more preferably of about 50 to about 110 °C, and in particular of about 50 to 100 °C.

[0169] In another embodiment, the method is conducted at a temperature of about -15 to about 20 °C, preferably of about -10 to about 10 °C, and in particular of about -5 to about 5 °C; optionally followed by elevating the temperature to about 30 to about 100 °C, preferably to about 40 to about 90 °C, and in particular of about 50 to about 80 °C.

[0170] Preferably, the reaction is done under atmospheric pressure. The reaction can however also be done under a pressure above atmospheric pressure, for example when a reaction temperature is chosen above the boiling point of any of the components of the reaction mixture.

[0171] After the reaction, the oxetane-containing compound can be isolated by standard means known to the skilled person, by e.g. concentration by vacuum distillation if the reaction is performed in a solvent or simple decharging from the reaction container.

[0172] In one embodiment, the method is conducted under inert gas atmosphere (e.g. nitrogen or argon), preferably under nitrogen atmosphere.

[0173] In one embodiment, the compound of formula (10) is present in the reaction from about 1 to about 2 eq, preferably from about 1 to about 1 .5 eq, more preferably from about 1 to about 1 .2 eq, even more preferably from about 1 to about 1.1 eq, of the total molar equivalents of functional groups selected from the group consisting of isocyanate, chloride, a,p-unsaturated carbonyl, and combinations thereof the compound (C-B).

[0174] In one embodiment, the oxetane-containing compound is a compound of formula (1). In one embodiment, the compound of formula (10) is obtained by a reaction of an alcohol oxetane of formula (20)

[0175] (20) with a diketene, wherein RAis H or C1-C10-alkyl.

[0176] In one embodiment, the compound of formula (10) is obtained by a reaction of an alcohol oxetane of formula (20), wherein RAis ethyl with diketene

[0177] The crude product of the respective reaction may be used directly as starting material in the method according to the second aspect.

[0178] As aforementioned, the present invention further relates in a third aspect to an oxetane-containing compound obtained by a method according to the inventive method (second aspect).

[0179] Embodiments (e.g. regarding the moieties and method conditions) are already above-outlined in connection with the inventive compounds and method and shall hold for the third aspect as well.

[0180] As aforementioned, the present invention further relates in a fourth aspect to a composition comprising an oxetane-containing compound as defined in the first or in the third aspect and an additive (A) selected from the group consisting of catalyst, reinforcement fibres, a filler, compounds comprising at least one a,p-unsaturated carbonyl group, epoxies, vinyl and allyl compounds, oxetanes, amines, isocyanates, cyanate esters, and combinations thereof.

[0181] Embodiments (e.g. regarding the moieties and method conditions) are already above-outlined and shall hold for the method, as well. In the following, embodiments of the method are described in further detail. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments. It is to be understood that the additive (A) (e.g. oxetane) is structurally different to the compound of formula (1) or the oxetane-containing compound according to the third aspect, respectively.

[0182] Preferably, the composition is a 3D-printing, a chemical anchoring, a coating, a painting, an electronic compatible (EMC), an adhesive, a sealant, a composite or a building and construction composition.

[0183] In one embodiment, the catalyst is selected from the group consisting of aliphatic mono-, di- and polyamines; aromatic mono-, di- and polyamines; carbocyclic mono-, di and polyamines; heterocyclic mono-, di- and polyamines; compounds containing a five- or six-membered nitrogencontaining heterocyclic ring; hydroxyamines; phosphines; phenols; and mixtures thereof. Preferably, the catalyst is a tertiary amine, more preferably selected form the group consisting of trialkyl amine such as triethylamine (TEA), 1 ,4-diazabicyclo[2.2.2]octane (DABCO), N,N-dimethylpyridin-4-amin, 1 ,1 ,3,3-tetramethylguanidine (TMG), N,N-dimethylisopropylamine, 1 ,8-diazabicyclo(5.4.0)undec-7- ene (DBU), and 1 ,5-diazabicyclo(4.3.0)non-5-ene (DBN), and in particular selected from the group consisting of 1 ,1 ,3,3-tetramethylguanidine (TMG), 1 ,4-diazabicyclo[2.2.2]octane (DABCO), triethylamine (TEA), N,N-dimethylisopropylamine, 1 ,8-diazabicyclo(5.4.0)undec-7-ene (DBU), and 1 ,5-diazabicyclo(4.3.0)non-5-ene (DBN).

[0184] In one embodiment, the catalyst is a cationic catalyst such as iodonium and sulfonium salts.

[0185] Suitable catalysts include but are not limited to diaryliodonium compounds or triarylsulfonium compounds paired with anions such as BF4-, B(C6F5)4-, PF6-, AsF6-, SbF6-, CF3SO3-, variations thereof. Suitable iodonium salts may be selected from the compounds selected from the group consisting of

[0186] . Suitable sulfonium salts may be selected from the group consisting of

[0187]

[0188] Examples of such catalyst are bis-(4-dodecylphenyl)iodonium hexafl uro anti mon ate in glycidyl ether, (sulfanediyldibenzene-4,1-diyl)bis(diphenylsulfonium) bis(hexafluoroantimonate)in digycidyl ether, and bis-(4-t-butylphenyl)-iodonium hexafluorophosphate. Further suitable cationic catalysts are available from Arkema.

[0189] In one embodiment, the catalyst is a radical catalyst. Suitable radical catalysts include but are not limited to dialkyl peroxides, diacyl peroxides, and azo compounds. Particularly suitable radical catalysts include dicumyl peroxide and 2,5-Dimethyl-2,5-di-(tert-butylperoxy)hexyne-3 (Trigonox 145-E85).

[0190] The amount of the catalyst can be varied to adapt to different applications and needs. Typically, the amount of the catalyst ranges from 0.05 to 10.0 wt%, more preferably from 0.1 to 7 wt%, even more preferably from 0.15 to 5 wt% based on the total amount of compound of formula (1) or oxetane- containing compound according to the third aspect, respectively.

[0191] In one embodiment, the reinforcement fibres are selected from the group consisting of carbon fibres; glass fibres, preferably E glass fibres or S glass fibres; aramid fibres (including KEVLAR®); basalt fibres (geotextile fibers); natural fibres, preferably flax, hemp, jute or sisal; fleeces; and woven fabrics (multi-layered or single layered); and mixtures thereof. In a preferred embodiment, the reinforcement fibres are carbon fibres such as polyacrylonitrile PAN based carbon fibres, glass fibres, basalt fibres, aramid fibres or natural fibres, or mixtures thereof.

[0192] In another preferred embodiment the reinforcement fibres are glass fibres, carbon fibres or aramid fibres, or mixtures thereof.

[0193] The reinforcement fibres may be pre-shaped fibres. The reinforcement fibres may be chopped or continuous, random or oriented, woven or non-woven, knitted or non-knitted or braided according to the requirements of any of various different portions of the desired structure of the composite material (also called fibre reinforced part) or the desired building and construction material (also called foundry shape).

[0194] The pre-shaped form of the reinforcement fibres may be selected in view of the desired form of e.g. the composite material, the fibre may have the form of a sheet, mat, bead, strand, thread, band, web, roving, band of rovings, bundle, or the like.

[0195] The amount of reinforcement fibres may vary depending on the desired need of e.g. the composite material. Reinforcement fibre content in the composition typically is in the range of up to 50 or even up to 80 wt% of the total weight of the composition, in another embodiment, the content of the reinforcement fibre may vary from 0.1 to 50 or even to 80 wt%, or from 1 to 50 or even to 80 wt%, or from 5 to 50 or even to 80 wt%, or from 10 to 50 or even to 80 wt%, or from 20 wt% to 50 or even to 80 wt% of the total weight of the composition.

[0196] In one embodiment, the filler is selected from the group consisting of organic fillers, preferably thermoplastics and elastomers; inorganic fillers, preferably glass microspheres, graphite or silica; and mineral powder fillers, preferably CaCO3, coated CaCO3, kaolin clay, SiO2 (e.g. sand), talc, graphite, corundum (a-ALOs), wollastonite, SiC, glass microspheres, mica, calcium silicate (Ca2O4Si), MgO, anhydrous calcium sulfate (CaSCM or anhydrite), ceramic hollow microspheres, fused mullite (Al2O3-SiO2), boron nitride (BN), vermiculite, or basalt; and mixtures thereof. Preferably, the filler is sand.

[0197] In a preferred embodiment, the filler is selected from the group consisting of CaCO3, coated CaCO3, kaolin clay, SiO2, wollastonite, boron nitride (BN), talc, and mixtures thereof.

[0198] In another preferred embodiment, the filler is selected from the group consisting of coated CaCO3, talc, boron nitride (BN), wollastonite, SiC and mixtures thereof. The fillers may be in particle, powder, sphere, chip and / or strand form and have an average particle size from nano scale to millimeters, preferably the fillers have an average particle size from 0.1 to 1000 pm, more preferably the fillers have an average particle size of from 0.5 to 500 pm.

[0199] The amount of fillers may vary and is preferably from 5 to 70 wt%, preferably from 15 to 50 wt%, more preferably from 15 to 45 wt%, based on the total weight of the composition (excluding any potential solvent).

[0200] In one embodiment, the composition comprises an additive (A) suitable for adhesive, sealant, coating, painting, chemical anchoring, or 3D-printing applications. In this connection, suitable additives (A) are compounds comprising at least one a,p-unsaturated carbonyl group, epoxies, vinyl and allyl compounds, oxetanes, amines, isocyanates, cyanate esters, and combinations thereof. a,p-unsaturated carbonyl groups include vinyl ketones, acrylates, and acrylamides. In one embodiment, the composition comprises a compound comprising at least two a,p-unsaturated carbonyl groups. 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.

[0201] Compounds comprising at least one a,p-unsaturated carbonyl group are suitably acrylates.

[0202] Suitable compounds comprising at least one a,p-unsaturated carbonyl group include alkyl acrylate such as methyl acrylate and 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. Suitable epoxies are selected from the group consisting of bisphenol A diglycidyl ether resins, bisphenol F diglycidyl ether resins, N,N,O-triglycidyl-3-aminophenol, N ,N ,O-triglycidy 1-4 aminophenol, N,N,N',N' tetraglycidyl-4,4'-methylenebisbenzenamine, 4, 4', 4" meth- ylidene-'trisphenol triglycidyl ether resins, naphthalenediol diglycidyl ethers, and mixtures thereof.

[0203] Suitable vinyl compounds include vinyl alcohol, styrene and derivatives thereof.

[0204] Amines may be an aromatic and / or an aliphatic amine. Suitably, the amine is a primary amine. Suitable primary amines include di- and polyamines, i.e. amines which include at least two primary amine groups.

[0205] In one embodiment, the primary amine is selected from aliphatic amines, cycloaliphatic amines, cycloaromatic amines, and combinations thereof. In one embodiment, the 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”).

[0206] The term “isocyanate” as used herein encompasses any compound comprising at least one isocyanate functionality. Suitable isocyanates may further comprising an alkyl group, an alkylene group, a (optionally bivalent) cycloalkyl group, or a (optionally bivalent) aromatic group. Isocyanates may comprise more than one isocyanate functionality, e.g. diisocyanates such as diphenylmethane 4,4'-diisocyanate, isophorondiisocyanat, hexamethylendiisocyanat, and prepolymers thereof or triisocyanates.

[0207] In one embodiment, the oxetane-containing compound is the compound of formula (1) according to the first aspect (including all embodiments).

[0208] In one embodiment, the composition comprises at least one additive (A) selected from the group consisting of catalyst, reinforcement fibres, and a filler.

[0209] In one embodiment, the composition comprises at least a catalyst.

[0210] The composition may further comprise ingredients selected from the group pigments, compounds comprising at least one maleimide functionality, diene resins, and combinations thereof.

[0211] Suitable pigments include inorganic pigments such as titanium dioxide and zinc dioxide, and organic pigments such as anthraquinone pigments, anthrathrone pigments, anthrapyrimidine pigments, azo pigments, azomethine pigments, quinacridone pigments, quinophthalone pigments, diketopyrrolopyrrol pigments, inanthrone pigments, isoindoline pigments, metal complex pigments, perinone pigments, perylene pigments, phthalocyanine pigments, pyranthrone pigments, pyrazolo- quinazolone pigments, and thioindigo pigments.

[0212] Compounds comprising at least one maleimide functionality may comprise two maleimide functionalities, i.e. that the compound is a bismaleimide. Suitable bismaleimides include 4,4'- Diphenylmethane-bismaleimide, Bisa llylnadic imide P, 4,4'-Dially lether bisphenol A, 2,2'-Dially I bisphenol A (DABA), and 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide.

[0213] Suitable diene resins include butadiene homopolymers, butadiene styrene copolymers, and maleinized polybutadienes.

[0214] As aforementioned, the present invention relates in a fifth aspect to a process of manufacturing a 3D-printed object, a coating, a paint, an EMC material, an adhesive, a sealant, a composite or building and construction material comprising the steps of i) contacting a composition comprising a compound according to the first aspect (including all embodiments) or the third aspect (including all embodiments) with an additive (A) selected from the group consisting of catalyst, reinforcement fibres, a filler, compounds comprising at least one a,p- unsaturated carbonyl group, epoxies, vinyl and allyl compounds, oxetanes, amines, isocyanates, cyanate esters, and combinations thereof to provide a mixture (M); and ii) curing said mixture (M).

[0215] Embodiments (e.g. regarding the moieties and conditions for the method of manufacturing an oxetane-containing compound) are already above-outlined and shall hold for the process, as well. In the following, embodiments of the process are described in further detail. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments.

[0216] In one embodiment, the invention relates to a process of manufacturing a composite or building and construction material comprising the steps of i) contacting a fibre or a filler with a composition comprising a compound of formula (1) as defined in the first aspect to provide a fibre composition or a foundry mix, respectively; and ii) curing said fibre composition or foundry mix, respectively.

[0217] In one embodiment, the process relates to the manufacturing of a composite material comprising the steps of i) contacting a fibre with a composition comprising a compound of formula (1) as defined in the first aspect to provide a fibre composition, and ii) curing said fibre composition. In one embodiment, the fibres are reinforcement fibres.

[0218] In one embodiment, the contacting is an impregnation of the fibres with said composition.

[0219] Preparation of the composite materials according to the invention can be achieved as follows: providing a compound of formula (1) and optionally a catalyst, intimately mixing the components together as necessary, casting the mixture into the desired form comprising reinforcement fibres, and then initiating polymerization of the mixture (e.g. by, inter alia, increasing temperature, irradiation (e.g. UV light), use of a catalyst, or other methods commonly known in the art).

[0220] In one embodiment, the process comprises:

[0221] (i) providing the compound of formula (1) and optionally adding a catalyst and / or a solvent to said compound of formula (1) to obtain a mixture (by intimately mixing), preferably a homogenous mixture;

[0222] (ii) providing a fibre structure;

[0223] (iii) placing said fibre structure in a mold or on a substrate;

[0224] (iv) impregnating said fibre structure with said mixture (from step (i)), optionally by applying elevated pressure and / or evacuating the air and solvent from the mold and fibre structure, preferably at a temperature of 50 to 150 °C; and curing said liquid mixture in cured laminates by applying a temperature of preferably 50 to 180 °C with heating steps for a time sufficient to achieve a degree of conversion that allows de-moulding of the parts..

[0225] In another embodiment, the impregnation in step (iv) is achieved using a method selected from the group consisting of pre-preg (hot melt and solvated), resin transfer molding, vacuum assisted resin transfer molding, Vacuum resin infusion, Seemann Composites Resin Infusion Molding Process, injection molding, compression molding, spray molding, pultrusion, hand laminating, filament winding, Quickstep process or Roctool process.

[0226] In another embodiment, the impregnation in step (iv) is achieved using a composite molding process method selected from the group consisting of pre-preg (hot melt and solvated), resin transfer molding, liquid resin infusion, Seemann Composites Resin Infusion Molding Process, vacumn assisted resin infusion, injection molding, BMC / SMC bulk and sheet molding compounds and EADS vacuum assisted process (VAP®).

[0227] Fibre content in the fibre composition or in the fibre reinforced parts typically is in the range of up to 50 or even up to 80 wt% of the total weight of the fibre resin composition or of the fibre reinforced part respectively, in another embodiment, the content of the fibre may vary from 0.1 to 50 or even to 80 wt%, or from 1 to 50 or even to 80 wt%, or from 5 to 50 or even to 80 wt%, or from 10 to 50 or even to 80 wt%, or from 20 wt% to 50 or even to 80 wt% of the total weight of the fibre resin composition or of the fibre reinforced part respectively.

[0228] In another embodiment, the process relates to the manufacturing of a building and construction material comprising the steps of i) mixing a filler with a composition comprising a compound of formula (1) as defined in the first aspect to give a foundry mix, and ii) curing said foundry mix.

[0229] In one embodiment, the filler is sand. The sand for use according to the process of the invention may be any sand that is suitable for use as a filler. Examples include silica sand, olivine sand, chromite sand, zircon sand, chamotte sand. The sand may comprise minor amounts of staurolite, graphite or coal, clay, talc, iron oxides, titanium oxides and / or anthracite. The clay may be kaolin and / or bentonite. The sand may further comprise cushioning material such as wood flour, saw dust, powdered husks, peat, and straw and / or cereal binders such as dextrin, starch, sulphite lye, and molasses.

[0230] The amount of the composition comprising a compound of formula (1) as defined in the first aspect relative to the amount of the filler (i.e. , sand) in the foundry mix may vary depending on the desired application, but is generally from 0.5% (w / w) to 15% (w / w), preferably from 1% (w / w) to 12.5% (w / w), more preferably from 2% (w / w) to 10% (w / w), especially from 1% (w / w) to 10% (w / w), more especially from 1% (w / w) to 2% (w / w), most especially from 0.5% (w / w) to 3% (w / w).

[0231] In the above embodiments, the applied oxetane-containing compound may also be the oxetane- containing compound according to the third aspect.

[0232] In one embodiment, the process relates to the manufacturing of a 3D-printed object comprising the curing steps repeatedly. Any known in the art 3D-printing method is suitable.

[0233] In one embodiment, the process relates to the manufacturing of a coating or a paint, wherein the process further comprises a coating step. The coating step is preferably performed between the step of i) contacting and the step of ii) curing.

[0234] As aforementioned, the present invention relates in a sixth aspect to a 3D-printed object, a coating, a paint, an EMC material, an adhesive, a sealant, a composite or building and construction material obtainable by a process according to the fifth aspect. Embodiments (e.g. regarding the moieties and process conditions) are already above-outlined and shall hold for the sixth aspect, as well. In the following, embodiments of the sixth aspect are described in further detail. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments.

[0235] Depending on the field of application, the glass transition temperature (Tg) of the product can be adjusted. Preferably, the composite or building and construction material has a glass transition temperature (Tg) of about 40 to about 200 °C, preferably of about 50 to about 180 °C. Preferably, the coating has a glass transition temperature (Tg) of about -90 to about 80 °C, preferably of about - 70 to about 70 °C such as of about -50 to about 60 °C.

[0236] In one embodiment, the 3D-printed object, the coating, the paint, the EMC material, the adhesive, the sealant, the composite or building and construction material is obtained by a process according to the fifth aspect.

[0237] As aforementioned, the present invention relates in a seventh aspect to the use of a compound according to the first or third aspect or a composition according to the fourth aspect in 3D-printing, in chemical anchoring, or in electronic encapsulation or for manufacturing a coating, a paint, an adhesive, a sealant, a composite or building and construction material.

[0238] Embodiments (e.g. regarding the moieties and conditions for the method of manufacturing an oxetane-containing compound) are already above-outlined and shall hold for the seventh aspect, as well. In the following, embodiments of the use are described in further detail. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments.

[0239] Depending on the field of application, the glass transition temperature (Tg) of the product can be adjusted. Preferably, the composite or building and construction material has a glass transition temperature (Tg) of about 40 to about 200 °C, preferably of about 50 to about 180 °C. Preferably, the coating has a glass transition temperature (Tg) of about -90 to about 80 °C, preferably of about - 70 to about 70 °C such as of about -50 to about 60 °C.

[0240] The skilled person in the art will be aware of how to use the respective ingredients for 3D-pri nti ng , chemical anchoring, or electronic encapsulation or for manufacturing a coating, a paint, an adhesive, a sealant, a composite or a building and construction material.

[0241] In one embodiment, the compound according to the first / third aspect or the composition according to the fourth aspect are used for producing a coating or a paint, wherein the coating comprises polyurea, polyurethane, and combinations thereof or wherein the coating comprises condensation products of epoxies and amines.

[0242] Suitably, the paint comprises at least one pigment.

[0243] In one embodiment, the compound of formula (1) is used for producing a coating or a paint comprising polyurea, polyurethane, and combinations thereof.

[0244] In one embodiment, the compound of formula (1) is used for producing a coating or a paint comprising condensation products of epoxies and amines.

[0245] As aforementioned, the present invention relates in an eighth aspect to a method for fastening anchoring elements in boreholes, wherein a composition according to the fourth aspect (including all embodiments) is placed in the boreholes and the anchoring element is inserted therein.

[0246] Embodiments (e.g. regarding the moieties and ingredients) are already above-outlined and shall hold for the eighth aspect, as well.

[0247] 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.

[0248] The present invention will be further illustrated by the following examples.

[0249] Examples

[0250] Example 1 : oxetane 1 methacrylate 1

[0251] 2.54 g of oxetane 1 , 143 mg of tBuOK and 1 .26 g of methacrylate 1were placed in a 50 mL round bottom flask. The whole setup was heated up to 85°C and left stirring for 24h. The reaction was then quenched by adding 10 mL of 0.1 M HCI. 10 mL of ethyl acetate were added to extract the product. The organic layer was dried over anhydrous sodium sulfate and the crude was concentrated to obtain 2.83 g of final product, 75.0% yield. Example 2: oxetane 1 methacrylate 2

[0252] 2.33 g of oxetane 1 , 126 mg of tBuOK and 1 .25 g of methacrylate 2 were placed in a 50 mL round bottom flask. The whole setup was heated up to 85°C and left stirring for 20h. The reaction was then quenched by adding 10 mL of 0.1 M HCI. 10 mL of ethyl acetate were added to extract the product. The organic layer was dried over anhydrous sodium sulfate and the crude was concentrated to obtain 2.58 g of final product, 74.6% yield.

[0253] Example 3: oxetane 1 acrylate 3

[0254] 2.52 g of oxetane 1 , 245 mg of tBuOK and 1.26 g of acrylate 3 (TMPTA) solution in tBuOH (3 mL) were placed in a 50 mL round bottom flask. The whole setup was heated up to 65°C and left stirring for 20h. The reaction was then quenched by adding 10 mL of 0.1 M HCI. 10 mL of ethyl acetate were added to extract the product. The organic layer was dried over anhydrous sodium sulfate and the crude was concentrated to obtain 2.22 g of final product, 58.7% yield.

[0255] Example 4: oxetane 1 acrylate 4

[0256] 2.85 g of oxetane 1 , 160 mg of tBuOK and 1 .25 g of acrylate 4 (PETTA) solution in tBuOH (4 mL) were placed in a 50 mL round bottom flask. The whole setup was heated up to 85°C and left stirring for 20h. The reaction was then quenched by adding 10 mL of 0.1 M HCI. 10 mL of ethyl acetate were added to extract the product. The organic layer was dried over anhydrous sodium sulfate and the crude was concentrated to obtain 3.27 g of final product, 81 % yield.

[0257] Example 5: oxetane 1 1 ,6-diisocyanatohexane

[0258] To a solution of oxetane 1 (11 .93 g, 2 equiv., 0.0590 mol), in dry THF (118.96 g, 1 .6497 mol, 56 equiv.) at 0 °C under inert atmosphere (N2), was added in small portions over 1 h t-BuOk (6.82 g, 2 equiv., 0.0589 mol). The obtained suspension was vigorously stirred at 0 °C under N2 for 1 h, then 1 ,6-diisocyanatohexane (5.03 g, 0.0296 mmol, 1 equiv.) was added in portions over 20 min. The reaction mixture was further stirred at 0 °C under N2. Then a solution of HCI (5% aq., 101 .17 g) was added in small portions at 0 °C. EtOAc (100.89 g) was added, and the phases separated; the aqueous phase was further extracted in EtOAc (3x100 mL), the unified organic phases were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The product was obtained as a white solid (16.98 g, quant, yield). Example 6: oxetane 1 bis(4-isocyanatophenyl)methane

[0259] To a solution of oxetane 1(7.96 g, 2 equiv., 0.0394 mol), in dry THF (101 .59 g, 1 .4088 mol, 72 equiv.) at 0 °C under inert atmosphere (N2), was added in small portions over 1 h t-BuOk (4.56 g, 2 equiv., 0.0394 mol). The obtained suspension was vigorously stirred at 0 °C under N2 for 1 h, then bis(4-isocyanatophenyl)methane (5.00 g , 0.0196 mmol, 1 equiv.) was added in portions over 20 min, and dry THF (21.22 g, 0.2943 mol, 15 equiv.). The suspension thus obtained was further stirred at 0 °C under N2 for 5 h then a solution of HCI (5% aq., 101.76 g) was added in small portions at 0°C. EtOAc (104.35 g) was added and the phases separated; the aqueous phase was further extracted in EtOAc (3x100 mL), and the unified organic phases were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The product was obtained as a white solid (7.14 g, 0.0110 mol, 56.04 % yield).

[0260] Example 7: oxetane 1 1 ,4-diisocyanatobenzene

[0261] To a solution of oxetane 1 (12.52 g, 2 equiv., 0.0619 mol), in dry THF (146.45 g, 2.0309 mol, 66 equiv.) at 0 °C under inert atmosphere (N2), was added in small portions over 1 h t-BuOk (7.17 g, 2 equiv., 0.0618 mol). The obtained suspension was vigorously stirred at 0 °C under N2 for 45 min, then 1 ,4-diisocyanatobenzene (5.02 g , 0.0309 mmol, 1 equiv.) was added in portions over 30 min, and dry THF (40.70 g, 0.5644 mol, 18 equiv.). The suspension thus obtained was further stirred at 0 °C under N2 for 30 min and then it was heated slowly to 65 °C and stirred overnight The suspension was allowed to cool to r.t. and then further cooled to 0 °C, and a solution of HCI (5% aq., 337.14 g) was added in small portions. The obtained suspension was further stirred at 0°C for around 1 h, and then the precipitate was isolated by filtration under vacuum. The product was obtained as a white solid (12.18 g, 0.0217 mol, 70.28 % yield). Example 8: oxetane 1 isophorone diisocyanate

[0262] To a solution of oxetane 1 (9.04 g, 2 equiv., 0.0447 mol), in dry THF (121.39 g, 1.6834 mol, 75 equiv.) at 0 °C under inert atmosphere (N2), was added in small portions over 1 h t-BuOk (5.19 g, 2 equiv., 0.0448 mol). The obtained suspension was vigorously stirred at 0 °C under N2 for 1 h, then isophorone diisocyanate (mixture of cis- and trans-isomers) (5.03 g , 0.0224 mmol, 1 equiv.) was added in portions over 15 min. The solution was further stirred at 0 °C for 5.5 h, and then a solution of HCI (5% aq., 105.64 g) was added in small portions at 0°C. EtOAc (105.22 g) was added, and the phases separated; the aqueous phase was further extracted in EtOAc (3x100 mL), the unified organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The product was obtained as a pale yellowish clear very viscous and sticky paste (14.44 g, quant, yield).

Claims

Claims1. Compound of formula (1)whereinRAis H or C1-C10-alkyl;RBis H or C1-C10-alkyl;Rcis H or C1-C10-alkyl;RDis H, C1-C1 O-alkyl, or C1-C10-acyl;X is 0 or NRN;B is C1-C40-alkylene, (C1-C20-alkoxylene)r,s,t-(C1-C20-alkylene)-C1-C20-alkoxylene, (C1- C10-alkylene)r,s,t-(carbocyclic group having between 4 and 20 carbon atoms)-( C1-C10-alkylene)r.s,t, (C1-C10-alkylene)r,s,t-(heterocyclic group having between 4 and 20 ring members)-(C1-C10- alkylene)r.s,t, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 4 and 10 carbon atoms)-C1- C6-alkylene-(carbocyclic group having between 4 and 10 carbon atoms)-(C1-C6-alkylene)r,s,t, alkoxylene-(carbocyclic group having between 4 and 10 carbon atoms)-C1-C6-alkylene-(carbocyclic group having between 4 and 10 carbon atoms)-alkoxylene, or paraffin-derived alkylene, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx, optionally wherein each CH2 group in the aforementioned groups is independently replaced by one or more same or different RY; m is 1 ; n is 0; o is at least 2;RNis H or C1-C5-alkyl; r, s, t are independently 0 or 1 ;Rxis C1-C6-alkyl, halogen, OH, carboxy, amino, or phenyl; and RYis -O- or C=O.

2. The compound of formula (1) according to claim 1 , whereinRAis H or C1-C4-alkyl, preferably H, methyl, or ethyl;RBis H or C1-C4-alkyl, preferably H or methyl;Rcis H or C1-C4-alkyl, preferably H or methyl;RDis H or C1-C4-acyl, preferably acetyl or propionyl;X is O or NH;B is C1-C30-alkylene, (C1-C10-alkoxylene)r,s,t-(C1-C10-alkylene)-C1-C10-alkoxylene, (C1-C6- alkylene)r,s,t-(carbocyclic group having between 5 and 12 carbon atoms)-(C1-C6-alkylene)r,s,t, (C1- C6-alkylene)r,s,t-(heterocyclic group having between 5 and 12 ring members)-(C1-C6-alkylene)r,s,t, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C6-alkylene- (carbocyclic group having between 5 and 6 carbon atoms)-(C1-C6-alkylene)r,s,t, alkoxylene- (carbocyclic group having between 5 and 6 carbon atoms)-C2-C4-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-alkoxylene, or paraffin-derived alkylene, preferably C1-C8- alkylene, (C1-C3-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3- alkylene)r.s,t, (C1-C3-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C3- alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3-alkylene)r, or heterocyclic group having between 5 and 6 ring members, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx; andRxis C1-C4-alkyl, halogen, or OH, preferably C1-C3-alkyl or F.

3. The compound of formula (1) according to claim 1 or 2, whereinRAis H or C1-C4-alkyl, preferably H, methyl, or ethyl;RDis H or C1-C4-acyl, preferably acetyl or propionyl;X is O or NH;B is C1-C10-alkylene, preferably C1-C6-alkylene, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx,o is at least 2, preferably 2 to 5; andRxis C1 -C4-a Iky I , preferably C1 -C3-alkyl.

4. The compound of formula (1) according to claim 1 or 2, whereinRAis H, methyl, or ethyl, preferably ethyl;RDis H or C1-C4-acyl, preferably acetyl or propionyl;B is C1-C10-alkylene, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C6-alkylene)r,s,t, or (C1-C6-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C6-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C6- alkylene)r, preferably C1-C8-alkylene, (C1-C3-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3-alkylene)r,s,t, or (C1-C3-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C3-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1- C3-alkylene)r, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx; m is 1 ; n is 0; o is at least 2; r, s, t are independently 0 or 1 ; andRxis C1-C4-alkyl, or phenyl, preferably C1-C3-alkyl.

5. A method of manufacturing an oxetane-containing compound, the method comprising the step of reacting a compound comprising at least one functional group selected from the group consisting of isocyanate, chloride, a,p-unsaturated carbonyl, and combinations thereof (C-B), with a compound of formula (10)whereinRAis H or C1-C10-alkyl;RMis C1-C10-alkyl.

6. The method according to claim 5, wherein the compound (C-B) comprises a backbone selected from the group consisting of C1-C40-alkylene, (C1-C20-alkoxylene)r,s,t-(C1-C20-alkylene)-C1-C20-alkoxylene, (C1-C10-alkylene)r,s,t-(carbocyclic group having between 4 and 20 carbon atoms)-(C1-C10-alkylene)r,s,t, (C1-C10-alkylene)r,s,t-(heterocyclic group having between 4 and 20 ring members)-(C1-C10-alkylene)r,s,t, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 4 and 10 carbon atoms)-C1-C6-alkylene-(carbocyclic group having between 4 and 10 carbon atoms)-(C1- C6-alkylene)r.s,t, alkoxylene-(carbocyclic group having between 4 and 10 carbon atoms)-C1-C6- alkylene-(carbocyclic group having between 4 and 10 carbon atoms)-alkoxylene, and paraffin, preferably C1-C30-alkylene, (C1-C10-alkoxylene)r,s,t-(C1-C10-alkylene)-C1-C10-alkoxylene, (C1- C6-alkylene)r,s,t-(carbocyclic group having between 5 and 12 carbon atoms)-(C1-C6-alkylene)r,s,t, (C1-C6-alkylene)r,s,t-(heterocyclic group having between 5 and 12 ring members)-(C1-C6- alkylene)r.s,t, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C6- alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C6-alkylene)r,s,t, alkoxylene-(carbocyclic group having between 5 and 6 carbon atoms)-C2-C4-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-alkoxylene, or paraffin, more preferably C1-C8- alkylene, (C1-C3-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3- alkylene)r.s,t, (C1-C3-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C3- alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3-alkylene)r, or heterocyclic group having between 5 and 6 ring members, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx, optionally wherein each CH2 group in the aforementioned groups is independently replaced by one or more same or different RY; r, s, t are independently 0 or 1 ;Rxis C1-C6-alkyl, halogen, OH, carboxy, amino, or phenyl; and RYis -O- or C=O.

7. The method according to claim 5 or 6, wherein the compound (C-B) is a compound comprising at least one functional group selected from the group consisting of isocyanate, a,p- unsaturated carbonyl, and combinations thereof and whereinRAis H or C1-C4-alkyl, preferably H, methyl, or ethyl; RMis C1-C6-alkyl, preferably methyl.

8. The method according to any one of claims 5 to 7, wherein the compound (C-B) comprises at least two, more preferably two to four a,p-unsaturated carbonyl groups and whereinRAis H, methyl, or ethyl, preferably methyl or ethyl;RMis C1-C6-alkyl, preferably methyl or ethyl;preferably wherein the compound (C-B) comprises a backbone selected from the group consisting of C2-C16-alkylene, preferably C2-C10-alkylene, more preferably C2-C5-alkylene, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx; andRxis C1-C3-alkyl, halogen, OH, or phenyl, preferably C1-C3-alkyl or OH.

9. The method according to any one of claims 5 to 7, wherein the compound (C-B) comprises at least two, preferably two to four, isocyanate group (C-B) and whereinRAis H, methyl, or ethyl, preferably methyl or ethyl; and RMis C1-C4-alkyl, preferably methyl; preferably wherein the compound (C-B) comprises a backbone selected from the group consisting of C2-C16-alkylene, (C1-C6-alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)- (C1-C6-alkylene)r.s,t, (C1-C6-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms)- C1-C6-alkylene-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C6-alkylene)r, or heterocyclic group having between 5 and 6 ring members, preferably C2-C10-alkylene, (C1-C3- alkylene)r,s,t-(carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3-alkylene)r,s,t, or (C1- C3-alkylene)r-(carbocyclic group having between 5 and 6 carbon atoms)-C1-C3-alkylene- (carbocyclic group having between 5 and 6 carbon atoms)-(C1-C3-alkylene)r, wherein each substitutable carbon atom in the aforementioned groups is independently unsubstituted or substituted with one or more same or different substituents Rx; and Rxis C1-C4-alkyl, F, or phenyl, preferably C1-C2-alkyl.

10. The method according to any one of claims 5 to 9, wherein method is conducted under basic conditions, preferably in the presence of alkali tert- butoxide; and / or wherein the method is conducted under inert atmosphere, preferably under nitrogen atmosphere; and / or wherein method is conducted in the presence of a solvent, preferably selected from the group consisting of an alcohol, an ether, and mixtures thereof.11 . The method according to any one of claims 5 to 10,wherein the method is conducted at elevated temperature, preferably at a temperature of about 40 to about 120 °C, more preferably of about 50 to about 110 °C, and in particular of about 50 to 100 °C; or wherein the method is conducted at a temperature of about -15 to about 20 °C, preferably of about -10 to about 10 °C, and in particular of about -5 to about 5 °C; optionally followed by elevating the temperature to about 30 to about 100 °C, preferably to about 40 to about 90 °C, and in particular of about 50 to about 80 °C.

12. An oxetane-containing compound obtained by a method according to any one of claims 5 to 11.

13. A composition comprising a compound according to any one of claims 1 to 4 or 12 and an additive (A) selected from the group consisting of catalyst, reinforcement fibres, a filler, compounds comprising at least one a,p-unsaturated carbonyl group, epoxies, vinyl and allyl compounds, oxetanes, amines, isocyanates, cyanate esters, and combinations thereof.

14. A process of manufacturing a 3D-printed object, a coating, a paint, an EMC material, an adhesive, a sealant, a composite or building and construction material comprising the steps of i) contacting a composition comprising a compound according to any one of claims 1 to 4 or 13 with an additive (A) selected from the group consisting of catalyst, reinforcement fibres, a filler, compounds comprising at least one a,p-unsaturated carbonyl group, epoxies, vinyl and allyl compounds, oxetanes, amines, isocyanates, cyanate esters, and combinations thereof to provide a mixture (M); and ii) curing said mixture (M).

15. A 3D-printed object, a coating, a paint, an EMC material, an adhesive, a sealant, a composite or building and construction material obtainable by a process according to claim 14.

16. Use of a compound according to any one of claims 1 to 4 or 12 or a composition according to claim 14 for use in 3D-printing, in chemical anchoring, or in electronic encapsulation or for manufacturing a coating, a paint, an EMC material, an adhesive, a sealant, a composite or building and construction material.

17. A method for fastening anchoring elements in boreholes, wherein a composition according to claim 13 is placed in the boreholes and the anchoring element is inserted therein.

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