Tetrafunctional oxetanyl silicon-containing monomer, and preparation method therefor and use thereof

Abstract

The present invention relates to the compound of formula (I), wherein all the variables are as defined in the specification. The present invention also relates to a preparation method for the compound of formula (I), a photocurable composition containing the compound of formula (I), a photocurable material prepared from the photocurable composition, and the use of the compound of formula (I) in the field of photocurable materials. The present invention has the following beneficial effects: (1) the compound of formula (I) has relatively good photopolymerization activity, and can be rapidly cured under the action of ultraviolet light; and (2) by means of the addition of the compound of formula (I), the surface hydrophobicity, heat resistance and tensile properties of a cured film can be improved.

Description

Tetrafunctional oxetane-based silicon-containing monomer, and preparation method and application thereof TECHNICAL FIELD

[0001] The present application relates to the field of photocurable materials, in particular to a tetrafunctional oxetane-based silicon-containing monomer. The present application also relates to a preparation method of the monomer, a photocurable composition comprising the monomer, a photocured material obtained from the photocurable composition, and the application of the monomer in the field of photocurable materials. BACKGROUND

[0002] Photopolymerization technology is a process of rapidly converting a chemically active liquid monomer or oligomer into a solid polymer by cross-linking initiated by ultraviolet light or visible light, which has been gradually developed since the 1960s. Compared with traditional thermal polymerization technology, photopolymerization has many advantages of its own, such as green and environmentally friendly, no consumption and volatilization of solvents, high efficiency, fast speed, low cost, etc. Photopolymerization technology has been widely used in many fields, such as photocurable coatings, photocurable inks and photocurable adhesives. With the continuous development and progress of photocuring technology, photopolymerization technology is now developing more rapidly in the fields of photoresist, laser three-dimensional imaging, three-dimensional modeling, etc. Compared with free radical photopolymerization, cationic photopolymerization system has the advantages of anti-oxygen inhibition, small volume shrinkage, good adhesion and high surface hardness, although the polymerization speed is slower. Oxetane has the advantages of small viscosity, low toxicity, small volatility and low volume shrinkage, and has been widely used as a cationic photopolymerization monomer. In addition, organosiloxane has excellent heat resistance, water repellency, flexibility, electrical insulation and physiological inertness. Although there are monomers containing organosiloxane and oxetane structures, most of the existing oxetane-based silicon-containing monomers are monofunctional monomers, which have a slow polymerization rate and cannot meet the application requirements. There is still a demand for monomers containing organosiloxane and oxetane structures, which have a fast polymerization rate and can impart better properties to the material, such as surface hydrophobicity, heat resistance and tensile properties. SUMMARY

[0003] The purpose of the present application is to provide a tetrafunctional oxetane-based silicon-containing monomer. The present inventors have found that the tetrafunctional oxetane-based silicon-containing monomer has a good polymerization rate and conversion rate, and can promote the polymerization of other cationic monomers, while imparting excellent tensile properties, heat resistance, surface hydrophobicity, etc. to the material.

[0004] Another purpose of the present application is to provide a method for preparing the tetrafunctional oxetane-based silicon-containing monomer of the present application. The preparation method is simple and easy to operate, has mild conditions, raw materials are easy to obtain, and the cost is low.

[0005] In particular, the present application relates to the following aspects:

[0006] 1. Compound of formula (I):

[0007] R1, R2, R3, and R4 are the same or different and are independently organic groups having 1-12 carbon atoms; R5, R6, R7, and R8 are the same or different and are independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; and L1, L2, L3, and L4 are the same or different and are independently linking groups having 2-30 carbon atoms.

[0008] 2. The compound of formula (I) according to item 1, wherein R1, R2, R3, and R4 are the same or different and are independently C6-C. 10 Aryl, C1-C 12 Alkyl, C1-C 12 Alkyl group, independently selected from NR a C2-C with non-adjacent heteroatoms of O and S 12 Alkyl groups or groups independently selected from NR a C2-C with non-adjacent heteroatoms of O and S 12 Alkoxy, where R a It is H or C1-C4 alkyl.

[0009] 3. The compound of formula (I) according to item 1, wherein

[0010] R1, R2, R3, and R4 may be the same or different and are independently C6-C. 10 aryl, C1-C6 alkyl, C1-C6 alkoxy, or one or more independently selected from NR a C2-C6 alkyl groups with non-adjacent heteroatoms of O and S, wherein R a It is H or C1-C4 alkyl; preferably, R1, R2, R3, and R4 are the same or different and are independently phenyl, C1-C4 alkyl, C1-C4 alkoxy, or are independently selected from NR by one or more. a C2-C4 alkyl groups with non-adjacent heteroatoms of O and S, wherein R a It is H or C1-C4 alkyl; and / or

[0011] R5, R6, R7, and R8 may be the same as or different from each other and are independently H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy, or C1-C4 haloalkoxy; and / or

[0012] L1, L2, L3, and L4 may be the same or different and are independently C2-C 10alkylene or C3-C 10 cycloalkylene.

[0013] 4. The compound of formula (I) according to item 1, wherein R1, R2, R3, R4 are the same or different and independently phenyl, C1-C4 alkyl, C1-C4 alkoxy or C2-C4 alkyl interrupted by one or more non-adjacent heteroatoms independently selected from NR a , O, S, wherein R a is H or C1-C4 alkyl; R5, R6, R7, R8 are the same or different and independently H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; and L1, L2, L3, L4 are the same or different and independently C2-C6 alkylene or C4-C8 cycloalkylene;

[0014] Preferably, R1, R2, R3, R4 are the same or different and independently C1-C4 alkyl; R5, R6, R7, R8 are the same or different and independently H or C1-C4 alkyl; L1, L2, L3, L4 are the same or different and independently C2-C4 alkylene or C5-C6 cycloalkylene.

[0015] 5. The compound of formula (I) according to item 1, which is a compound of formula (I-1):

[0016] 6. A process for the preparation of a compound of formula (I) according to any one of items 1 to 5, comprising reacting a compound of formula (II) with a compound of formula (III) to give a compound of formula (I):

[0017] wherein R a is R5, R6, R7, R8 and is independently defined as in any one of items 1 and 3 to 5, and L is an alkenyl or cycloalkenyl group having 2 to 30 carbon atoms,

[0018] wherein R1, R2, R3 and R4 are defined as in any one of items 1 to 5.

[0019] 7. The process according to item 6, wherein

[0020] the reaction of the compound of formula (II) with the compound of formula (III) is carried out in the presence of Karstedt's catalyst or Speier's catalyst, preferably the amount of catalyst is 2 to 500 ppm, preferably 80 to 200 ppm, based on the weight of the compound of formula (III); and / or

[0021] The molar ratio of the compound of formula (II) to the compound of formula (III) is 4:1 to 6:1, preferably 4:1 to 4.5:1 ; and / or

[0022] The reaction between the compound of formula (II) and the compound of formula (III) is carried out at 80 to 110 °C, preferably 85 to 100 °C; and / or

[0023] The reaction between the compound of formula (II) and the compound of formula (III) is carried out for 6 to 20 hours, preferably 10 to 16 hours.

[0024] 8. A photocurable composition comprising the compound of formula (I) according to any one of items 1 to 5 as a polymerizable monomer.

[0025] 9. A photocured material obtained from the photocurable composition according to item 8.

[0026] 10. Use of the compound of formula (I) according to any one of items 1 to 5 in photocured coatings, adhesives, inks and photoresists. BRIEF DESCRIPTION OF DRAWINGS

[0027] Figure 1 is a graph of the conversion of cycloaliphatic epoxy in a system comprising the compound (I-1) prepared in Example 1 as a function of irradiation time.

[0028] Figure 2 is a graph of the conversion rate of compound (I-1) in a system comprising the compound (I-1) prepared in Example 1 as a function of irradiation time.

[0029] Figure 3 is a graph of the water contact angle of a blank E4221 / VOH cured film and a cured film of a system comprising the compound (I-1) prepared in Example 1.

[0030] Figure 4 is a graph of the thermogravimetric curve of a blank E4221 / VOH cured film and a cured film of a system comprising the compound (I-1) prepared in Example 1.

[0031] Figure 5 is a graph of the mechanical properties of a blank E4221 / VOH cured film and a cured film of a system comprising the compound (I-1) prepared in Example 1.

[0032] DETAILED DESCRIPTION

[0033] In the following description of the application, the numerical values in this application can be considered to be modified by the word "about" unless otherwise expressly stated. However, the inventors have reported the numerical values in the examples as precisely as possible, although these numerical values inevitably include certain errors.

[0034] In the present application, the specific or preferred embodiments of the present application can be combined, unless explicitly excluded. In addition, each element of the embodiments of the present application is a specific preferred selection of the corresponding generic technical feature. If the generic technical feature can be combined with other generic features, the element of the embodiment, i.e. the specific preferred selection, can also be combined with the other generic features. These combinations shall be considered as part of the originally filed content of the present application. DETAILED DESCRIPTION

[0035] According to one aspect of the present application, there is provided a compound of the following formula (I):

[0036] wherein R1, R2, R3, R4are the same or different and independently an organic group having 1 to 12 carbon atoms; R5, R6, R7, R8are the same or different and independently H, halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6hydroxyalkyl, C1-C6alkoxy, or C1-C6haloalkoxy; and L1, L2, L3, L4are the same or different and independently a linking group having 2 to 30 carbon atoms.

[0037] In one embodiment of the present application, the organic group having 1 to 12 carbon atoms is C6-C 10 aryl, C1-C 12 alkyl, C1-C 12 alkoxy, C2-C a alkyl interrupted by one or more non-adjacent heteroatoms independently selected from NR 12 , O, S, or C2-C a alkoxy interrupted by one or more non-adjacent heteroatoms independently selected from NR 12 , O, S, wherein R a is H or C1-C4alkyl.

[0038] In the present application, the prefix "C n -C m " in each case denotes the number of carbon atoms comprised in the group as n-m.

[0039] "Halogen" means fluorine, chlorine, bromine and iodine. In the present application, it is preferred that halogen includes fluorine, chlorine or a combination thereof.

[0040] The term "C n -C m"Alkyl" means a branched or unbranched saturated hydrocarbon group having n-m, for example 1-12, preferably 1-6, in particular 1-4 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and isomers thereof, in particular methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 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, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl and the like. C1-C6alkyl can be methyl, ethyl, propyl, butyl, pentyl, hexyl and isomers thereof, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, t-butyl, n-pentyl, isopentyl, n-hexyl and the like. C1-C4alkyl can be methyl, ethyl, propyl, butyl and isomers thereof, in particular methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl.

[0041] The term "C n -C mAlkenyl" means a branched or unbranched hydrocarbon group having n-m carbon atoms, for example 2 to 12, preferably 2 to 6, in particular 2 to 4, and one C=C double bond, such as ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl and the isomers thereof, in particular ethenyl, n-propenyl, 1-methylethenyl, n-but-enyl, 1-methylpropenyl, 2-methylpropenyl, 1,1-dimethylethenyl, n-pentenyl, 1-methylbutenyl, 2-methylbutenyl, 3-methylbutenyl, 2,2-dimethylpropenyl, 1-ethylpropenyl, 1,2-dimethylpropenyl, n-hexenyl, 1-methylpentenyl, 2-methyl-pentenyl, 3-methylpentenyl, 4-methylpentenyl, 1,1-dimethylbutenyl, 1,2-dimethylbutenyl, 1,3-dimethylbutenyl, 2,2-dimethylbutenyl, 2,3-dimethylbutenyl, 3,3-dimethylbutenyl, 1-ethylbutenyl, 2-ethylbutenyl, 1,1,2-trimethylpropenyl, 1,2,2-trimethylpropenyl, 1-ethyl-1-methylpropenyl, 1-ethyl-2-methylpropenyl, n-heptenyl, n-octenyl, 2-ethylhexenyl, n-nonenyl, n-decenyl, n-undecenyl, n-dodecenyl and the like. C2-C6Alkenyl can be ethenyl, propenyl, butenyl, pentenyl, hexenyl and the isomers thereof, in particular ethenyl, n-propenyl, isopropenyl, n-but-enyl, 2-butenyl, t-butenyl, n-pentenyl, isopentenyl, n-hexenyl and the like. C2-C4Alkenyl can be ethenyl, propenyl, butenyl and the isomers thereof, in particular ethenyl, n-propenyl, 1-methylethenyl, n-but-enyl, 1-methylpropenyl, 2-methylpropenyl or 1,1-dimethylethenyl.

[0042] The term "C6-C m Aryl" means a monocyclic, bicyclic or polycyclic aromatic hydrocarbon group having 6-m carbon atoms, for example 6 to 10 carbon atoms. As C6-C m Examples of aryl groups that can be mentioned are phenyl, tolyl, ethylphenyl, propylphenyl, butylphenyl, xylyl, methyl-ethylphenyl, diethylphenyl, methyl-propylphenyl and naphthyl, and the like; preferably phenyl or naphthyl, in particular phenyl.

[0043] The term "C n -C m Alkoxy" means a C n -C m Alkyl group, for example C1-C n -C m Alkyl group, for example C1-C n -C m Alkyl group, for example C1-C12 Alkoxy groups, more preferably C1-C6 alkoxy groups, and especially preferably C1-C4 alkoxy groups. C1-C6 alkoxy groups can be methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, and their isomers, particularly methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, 2-butoxy, tert-butoxy, n-pentoxy, isopentoxy, n-hexoxy, etc. C1-C4 alkoxy groups can be methoxy, ethoxy, propoxy, butoxy, and their isomers, particularly methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, or tert-butoxy.

[0044] The term "C" used in this article n -C m "Halogenated alkyl" refers to a C-aryl group that has been substituted with one or more identical or different halogen atoms. n -C m Alkyl groups, such as C1-C 12 Haloalkyl, preferably C1-C6 haloalkyl, particularly preferably C1-C4 haloalkyl. As a C n -C m Examples of haloalkyl groups may include monochloromethyl, monochloroethyl, dichloroethyl, trichloroethyl, monochloropropyl, dichloromethylethyl, monochlorobutyl, dichloromethylpropyl, trichloromethylpropyl, monochloropentyl, dichloromethylbutyl, monochlorohexyl and their isomers, particularly 1-chloromethylethyl, 1,1-dichloromethylethyl, 1-chloromethylpropyl, 2-chloromethylpropyl, 1,1-dichloromethylpropyl, 1,2-dichloromethylpropyl, 2,2-dichloromethylpropyl, 1,1,2-trichloromethylpropyl, 1,2,2-trichloroethylethyl, and 1,2,2-trichloromethylpropyl. Methylpropyl, 1-chloromethylbutyl, 2-chloromethylbutyl, 3-chloromethylbutyl, 1-chloroethylpropyl, 1,1-dichloromethylbutyl, 1,2-dichloromethylbutyl, 1,3-dichloromethylbutyl, 2,2-dichloromethylbutyl, 2,3-dichloromethylbutyl, 3,3-dichloromethylbutyl, 1-chloromethylpentyl, 2-chloromethylpentyl, 3-chloromethylpentyl, 4-chloromethylpentyl, 1-chloroethylbutyl, 2-chloroethylbutyl, 1-chloroethyl-1-methylpropyl, 1-ethyl-2-chloromethylpropyl, etc.

[0045] The term "C" used in this article n -C m "Haloalkoxy" refers to a carbon atom that has been substituted with one or more identical or different halogen atoms. n -C m Alkoxy groups, such as C1-C 12 Haloalkoxy groups, more preferably C1-C6 haloalkoxy groups, and especially preferably C1-C4 haloalkoxy groups. As a C n -C mExamples of haloalkoxy groups include chloromethoxy, 2-chloroethoxy, 3-chloropropoxy, 4-chlorobutoxy, 5-chloropentoxy, 6-chlorohexoxy and their isomers, especially chloromethoxy, 2-chloroethoxy, 3-chloron-propoxy, 2-chloroisopropoxy, 4-chloron-butoxy, 3-chlorosec-butoxy, 2-chlorotert-butoxy, 5-chloron-pentoxy, 4-chloroisopentoxy, 6-chloron-hexoxy, etc.

[0046] The term "C" used in this article n -C m "Hydroxyalkyl" refers to the hydroxyalkyl group in C n -C m alkyl corresponding to open chain C n -C m In alkanes, a carbon atom with a hydroxyl group bonded to it is a C-axis. n -C m Alkyl groups, such as C1-C6 hydroxyalkyl groups, especially C1-C4 hydroxyalkyl groups, such as hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl and their isomers, particularly hydroxymethyl, hydroxyethyl, hydroxy-n-propyl, hydroxyisopropyl, hydroxy-n-butyl, hydroxysec-butyl, hydroxytert-butyl, hydroxy-n-pentyl, hydroxy-n-hexyl, etc.

[0047] The term "C" used in this article n -C m "Alkylene" refers to a branched or unbranched saturated alkylene group having 1-10 carbon atoms, preferably 1-6, and particularly preferably 1-4 carbon atoms, such as methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, and their isomers, especially methylene, ethylene, n-propylene, methyl ethylene, n-butylene, 1-methylpropylene, 2-methylpropylene, 1,1-dimethylethylene, n-pentylene, 1-methylbutylene, 1,1-dimethylpropylene, 1-ethylpropylene, 1,1-dimethylpropylene, 1,2-dimethylpropylene, n-hexylene, 1-methylpentylene, 1,1-dimethylbutylene. The alkylene groups can be methylene, ethylene, propylene, butylene, pentylene, hexylene, octylene, 1-ethylhexylene, nonylene, decylene, etc. C1-C6 alkylene groups can be methylene, ethylene, propylene, butylene, pentylene, hexylene, and their isomers, especially methylene, ethylene, propylene, isopropylene, butylene, tert-butylene, pentylene, isopentylene, hexylene, etc. C1-C4 alkylene groups can be methylene, ethylene, propylene, butylene, and their isomers, especially methylene, ethylene, propylene, 1-methylethylene, butylene, 1-methylpropylene, or 1,1-dimethylethylene.

[0048] The term "C" used in this article n-C m Cycloalkylene" means a cycloalkylene group having n-m, for example 3-10, preferably 4-8, particularly preferably 5-6 carbon atoms, for example cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene, cyclononylene, cyclodecylene and isomers thereof, in particular 1,2-cyclopropylene, 1,2-cyclobutylene, 1,3-cyclobutylene, 1,2-cyclopentylene, 1,3-cyclopentylene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclohexylene, 1 -methyl-2,4-cyclohexylene, 1 -methyl-2,6-cyclohexylene, 1,3-cycloheptylene, 1,4-cycloheptylene, 1,3-cyclooctylene, 1,4-cyclooctylene, 1,5-cyclooctylene, 1,3-cyclononylene, 1,4-cyclononylene, 1,5-cyclononylene, 1,3-cyclodecylene, 1,4-cyclodecylene, 1,5-cyclodecylene and the like. C4-C8cycloalkylene can be cyclobutylene, cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene and isomers thereof, in particular 1,2-cyclobutylene, 1,3-cyclobutylene, 1,2-cyclopentylene, 1,3-cyclopentylene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclohexylene, 1 -methyl-2,4-cyclohexylene, 1 -methyl-2,6-cyclohexylene, 1,3-cycloheptylene, 1,4-cycloheptylene, 1,3-cyclooctylene, 1,4-cyclooctylene, 1,5-cyclooctylene and the like. C5-C6cycloalkylene can be cyclopentylene, cyclohexylene and isomers thereof, in particular 1,2-cyclopentylene, 1,3-cyclopentylene, 1,2-cyclohexylene, 1,3-cyclohexylene or 1,4-cyclohexylene.

[0049] The term "C n -C m Cycloalkenyl" means a cycloalkenyl group having n-m, for example 3-10, preferably 4-8, particularly preferably 5-6 carbon atoms and one C=C double bond, for example cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenenyl, cyclodecenyl and isomers thereof. C4-C8cycloalkenyl can be cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl and isomers thereof. C5-C6cycloalkenyl can be cyclopentenyl, cyclohexenyl and isomers thereof.

[0050] In the compounds of the formula (I) according to the application, R1, R2, R3, R4are identical or different and are generally independently of one another C6-C 10 aryl, C1-C 12 alkyl, C1-C 12 alkoxy, C2-C a alkyl interrupted by one or more non-adjacent heteroatoms independently selected from the group consisting of NR 12 alkyl interrupted by one or more non-adjacent heteroatoms independently selected from the group consisting of NRa C2-C6alkyl interrupted by non-adjacent heteroatoms selected from the group consisting of N, O, S, wherein R 12 C2-C6alkyl interrupted by non-adjacent heteroatoms selected from the group consisting of N, O, S, wherein R a is H or C1-C4alkyl, for example C1-C6alkoxy-C1-C6alkyl, C1-C6alkylamino-C1-C6alkyl, C1-C6alkylthio-C1-C6alkyl, C1-C6alkoxy-C1-C6alkoxy, C1-C6alkylamino-C1-C6alkylamino or C1-C6alkylthio-C1-C6alkylthio. Preferably, R1, R2, R3, R4are the same or different and independently C6-C 10 C2-C6alkyl interrupted by non-adjacent heteroatoms selected from the group consisting of N, O, S, wherein R a C2-C6alkyl interrupted by non-adjacent heteroatoms selected from the group consisting of N, O, S, wherein R a C2-C6alkyl interrupted by non-adjacent heteroatoms selected from the group consisting of N, O, S, wherein R a C2-C6alkyl interrupted by non-adjacent heteroatoms selected from the group consisting of N, O, S, wherein R a C2-C6alkyl interrupted by non-adjacent heteroatoms selected from the group consisting of N, O, S, wherein R

[0051] In the compounds of the present application, R5, R6, R7, R8are the same or different and independently typically H, halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6hydroxyalkyl, C1-C6alkoxy, or C1-C6haloalkoxy. Preferably, R5, R6, R7, R8are the same or different and independently H, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4hydroxyalkyl, C1-C4alkoxy, or C1-C4haloalkoxy. Particularly preferably, R5, R6, R7, R8are the same or different and independently H or C1-C4alkyl. For example, R5, R6, R7, R8are the same or different and independently H, chloro, bromo, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, t-butoxy, hydroxymethyl, hydroxyethyl, hydroxy-n-propyl, hydroxy-i-propyl, hydroxy-n-butyl, hydroxy-s-butyl, or hydroxy-t-butyl.

[0052] In the compounds of the present application, L1, L2, L3, L4are the same or different and independently C2-C 10 alkylene or C3-C 10 cycloalkylene. Preferably, L1, L2, L3, L4are the same or different and independently C2-C6alkylene or C4-C8cycloalkylene. Particularly preferably, L1, L2, L3, L4are the same or different and independently C2-C4alkylene or C5-C6cycloalkylene.

[0053] In some preferred embodiments of the present application,

[0054] R1, R2, R3, R4are the same or different and independently C6-C 10 aryl, C1-C6alkyl, C1-C6alkoxy, or C2-C6alkyl interrupted by one or more non-adjacent heteroatoms independently selected from NR a , O, S, wherein R a is H or C1-C4alkyl; Preferably, R2, R3, R4are the same or different and independently phenyl, C1-C4alkyl, C1-C4alkoxy, or C2-C4alkyl interrupted by one or more non-adjacent heteroatoms independently selected from NR a , O, S, wherein R a is H or C1-C4alkyl;

[0055] R5, R6, R7, R8are the same or different and independently H, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4hydroxyalkyl, C1-C4alkoxy, or C1-C4haloalkoxy; and

[0056] L1, L2, L3, L4are the same or different and independently C2-C10 alkylene or C3-C 10 cycloalkylene.

[0057] In some preferred embodiments of the present application,

[0058] R1, R2, R3, R4are the same or different and independently phenyl, C1-C4alkyl, C1-C4alkoxy or C2-C4alkyl interrupted by one or more non-adjacent heteroatoms independently selected from NR a , O, S, wherein R a is H or C1-C4alkyl; R5, R6, R7, R8are the same or different and independently H, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4hydroxyalkyl, C1-C4alkoxy or C1-C4haloalkoxy; and L1, L2, L3, L4are the same or different and independently C2-C6alkylene or C4-C8cycloalkylene.

[0059] Preferably, R1, R2, R3, R4are the same or different and independently C1-C4alkyl; R5, R6, R7, R8are the same or different and independently H or C1-C4alkyl; and L1, L2, L3, L4are the same or different and independently C2-C4alkylene or C5-C6cycloalkylene.

[0060] In another embodiment of the present application, the compound of formula (I) is a compound of formula (I-1):

[0061] According to a second aspect of the present application, there is provided a process for the preparation of a compound of formula (I) according to the present application, comprising reacting a compound of formula (II) with a compound of formula (III) to obtain a compound of formula (I):

[0062] wherein R a is R5, R6, R7, R8and is independently as defined in any one of items 1 and 3 to 5, and L is an alkenyl or cycloalkenyl group having 2 to 30 carbon atoms,

[0063] wherein R1, R2, R3and R4are as defined for the compound of formula (I).

[0064] The compound of formula (III) contains a hydrogen atom on the silicon atom, thus the compound of formula (III) can be referred to as a hydrogen-containing silicone oil. The compound of formula (III) can be synthesized according to conventional methods or can be obtained from commercial sources. The addition reaction of the hydrogen atom bonded to the silicon atom in the compound of formula (III) to the unsaturated carbon-carbon double bond in the compound of formula (II) is of a type known in the art.

[0065] Generally, the reaction is carried out in the presence of a catalyst. As the catalyst suitable for the reaction, Karstedt catalyst or Speier catalyst is generally used. The amount of the catalyst is also conventional. Generally, the amount of the catalyst is 2 to 500 ppm, preferably 80 to 200 ppm, based on the weight of the compound of the formula (III).

[0066] The reaction of the compound of the formula (II) with the compound of the formula (III) is generally carried out in a solvent. As the type of the solvent, there is no particular limitation as long as the compound of the formula (III), the compound of the formula (II) and the catalyst are dissolved and do not participate in the reaction between the compound of the formula (II) and the compound of the formula (III), and preferably the solvent is also advantageous for the precipitation of the product, i.e. the compound of the formula (I). As the solvent, an organic solvent is generally used, and preferably petroleum ether, dichloromethane, toluene or any mixture thereof is used. The amount of the solvent is also conventional, and generally the amount of the solvent is 2 to 20 times, preferably 8 to 15 times, the total weight of the compound of the formula (III) and the compound of the formula (II).

[0067] Advantageously, the molar ratio of the compound of the formula (II) to the compound of the formula (III) is 4:1 to 6:1, preferably 4:1 to 4.5:1.

[0068] In order to achieve the above reaction, generally the compound of the formula (III) is dissolved in the solvent with the catalyst and aged for a certain period of time, then the compound of the formula (II) is contacted therewith, and then the temperature is raised to the reaction temperature and maintained for a certain period of time to obtain the compound of the formula (I).

[0069] The aging is generally carried out at an elevated temperature, generally at 40 to 70°C, preferably at 45 to 60°C. The aging time is generally 20 to 60 minutes, preferably 30 to 50 minutes.

[0070] The reaction temperature between the compound of the formula (II) and the compound of the formula (III) is generally 80 to 110°C, preferably 85 to 100°C.

[0071] The reaction time of the reaction between the compound of the formula (II) and the compound of the formula (III) at the reaction temperature is generally 6 to 20 hours, preferably 10 to 16 hours.

[0072] Of course, the reaction can be advantageously carried out under stirring. After the completion of the reaction, the compound of the formula (I) is obtained by a conventional work-up. The work-up generally includes filtration or centrifugation to remove solid impurities, rotary evaporation to remove the solvent, and further distillation under reduced pressure to remove the solvent.

[0073] The compound of the formula (I) of the present application has good photopolymerization activity and can be rapidly cured under the action of ultraviolet light. The addition thereof can improve the surface hydrophobicity, heat resistance and tensile properties of the cured film.

[0074] According to a third aspect of the present invention, a photocurable composition is provided, comprising a compound of formula (I) as a polymerizable monomer. In addition to comprising the compound of formula (I) of the present invention, the photocurable composition may also comprise a cationic photoinitiator for ring-opening polymerization (a photoinitiator capable of initiating cationic polymerization) and optionally other monomers or oligomers containing cationic photocurable groups such as vinyl ether double bonds, alicyclic epoxy groups, or oxetane groups, for example, 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexylcarbamate (E4221) or 4-vinylepoxycyclohexane (VOH). The photocurable composition of the present invention can be a photocurable coating composition, an adhesive composition, a photocurable ink composition, or a photoresist composition, etc. After curing, the resulting cured product exhibits good tensile properties, excellent hydrophobicity, and good heat resistance.

[0075] Iodonium salts and thioonium salts are commonly used photoinitiators for ring-opening polymerization. Advantageously, the iodonium salt photoinitiators and thioonium salt photoinitiators respectively have the following general formulas (A) and (B):

[0076] in

[0077] R a R b R c R d and R e Each is an unreplaced C6-C. 10 aryl, or selected from halogen, nitro, carbonyl, C1-C 12 Alkyl, C1-C 12 Alkoxy, phenylthio, phenyl, and substituted phenyl groups substituted at C6-C 10 The aryl group, preferably phenyl or naphthyl, or a phenyl or naphthyl group substituted with a substituent selected from halogens, nitro groups, C1-C6 alkyl groups, and substituted phenyl groups, wherein the substituted phenyl group comprises one or more substituents selected from halogens, nitro groups, C1-C6 alkyl groups, and C1-C6 alkoxy groups; and

[0078] Y and Z are non-nucleophilic anions, such as trifluoromethanesulfonate, toluenesulfonate, C1-C6 carboxylate, and BF4. - ClO4 - PF6 - AsF6 - Or SbF6 - .

[0079] For example, as the photoinitiator, one or more selected from the group consisting of 4-(phenylthio)phenyl diphenylsulfonium hexafluorophosphate, 4-(phenylthio)phenyl diphenylsulfonium hexafluoroantimonate, bis(4-(diphenylsulfonio)phenyl) sulfide bis-hexafluorophosphate, bis(4-(diphenylsulfonio)phenyl) sulfide bis-hexafluoroantimonate, 10-(4-biphenylyl)-2-isopropylthioxanthone-10-sulfonium hexafluorophosphate, 10-(4-biphenylyl)-2-isopropylthioxanthone-10-sulfonium hexafluoroantimonate, diphenyliodonium hexafluorophosphate (810), 4-octyloxydiphenyliodonium hexafluorophosphate, 4-octyloxydiphenyliodonium hexafluoroantimonate, 4-isobutylphenyl 4'-methylphenyl iodonium hexafluorophosphate, 4-isobutylphenyl 4'-methylphenyl iodonium hexafluoroantimonate, bis(4-dodecylphenyl) iodonium hexafluoroantimonate, bis(4-dodecylphenyl) iodonium hexafluorophosphate, bis(4-tert-butylphenyl) iodonium hexafluorophosphate, or bis(4-tert-butylphenyl) iodonium hexafluoroantimonate can be used.

[0080] The amount of the photoinitiator used in the present application is conventional. The content of the photoinitiator is usually 0.1 to 5 mol%, preferably 0.5 to 2 mol%, based on the total amount of the photopolymerizable monomers.

[0081] The photocurable composition of the present application can further contain a sensitizer. As the sensitizer, for example, benzophenone and its derivatives such as 4-(4-methylphenylthio)benzophenone or 4,4'-bis(diethylamino)benzophenone, thioxanthone and its derivatives such as 2-isopropylthioxanthone, anthraquinone and its derivatives such as 2-ethylanthraquinone, coumarin derivatives such as 5,7-dimethoxy-3-(4-dodecylbenzoyl)coumarin, camphorquinone, phenothiazine and its derivatives, 3-(aroylmethylene)thiazolines, rhodanine and its derivatives, eosin, rhodamine, acridine, cyanine, merocyanine dyes; preferably benzophenone and its derivatives, thioxanthone and its derivatives, anthraquinone and its derivatives, coumarin and its derivatives, and especially preferably 2-isopropylthioxanthone can be mentioned.

[0082] The amount of the sensitizer used in the present application is conventional. The content of the sensitizer is usually 0.1 to 5 mol%, preferably 0.3 to 1 mol%, based on the total amount of the photopolymerizable monomers.

[0083] According to a fourth aspect of the present application, there is provided a photocured material obtained by photocuring the photocurable composition of the present application. The photocuring conditions are not particularly limited as long as the photocurable composition of the present application is photocured. The photocured material has the advantages of good tensile properties, excellent hydrophobic properties, and good heat resistance due to containing the monomer unit derived from the compound of formula (I) of the present application.

[0084] According to a last aspect of the present application, there is provided the use of a compound of formula (I) as a photocurable monomer in the field of photocurable materials.

[0085] The application will be further described in conjunction with specific examples. In the present application, all parts and percentages are by weight unless otherwise explicitly stated.

[0086] Examples

[0087] The experimental methods used in the following examples are conventional unless otherwise specified.

[0088] The materials, reagents and the like used in the following examples are commercially available unless otherwise specified. Experimental materials and reagents:

[0089] Toluene: CR Beijing Chemical Plant

[0090] Tetramethylcyclotetrasiloxane (D4H): AR Bide Pharmatech

[0091] 4-Vinyl-1,1,3,3-tetramethylcyclotetrasiloxane (VOH): AR Anjie Chemical

[0092] 1,3-Divinyl-1,1,3,3-tetramethyldisiloxane platinum (0) (Karstedt catalyst): AR Bide Pharmatech

[0093] Diphenyliodonium hexafluorophosphate (810): AR Shanghai Aldrich Biochemical Technology Co., Ltd.

[0094] 2-Isopropylthioxanthone (ITX): AR Shanghai Aldrich Biochemical Technology Co., Ltd.

[0095] 3,4-Epoxy cyclohexylmethyl 3,4-epoxy cyclohexylcarboxylate (E4221): AR Bide Pharmatech

[0096] Example 1

[0097] In a three-necked flask equipped with a temperature probe and a reflux condenser, 5 mmol of hydrosilicone oil (tetramethylcyclotetrasiloxane, corresponding to a compound of formula (III) in which R1, R2, R3, R4 are methyl) and 0.317 g of Karstedt catalyst at a concentration of 100 ppm were dissolved in 100 ml of anhydrous toluene, then warmed to 60°C and maintained for 40 min. Then 22 mmol of compound (II) (in which R aTo the compound (I-1) (X1 mol) and E-MA (X2 mol) in a brown bottle, 0.5X1 mol of 2-isopropylthioxanthone (ITX) and 0.5X1 mol of 2,2-dimethoxy-2-phenylacetophenone (DMPA) were added and stirred uniformly, and stored in dark. The molar ratio of each component of the photocuring composition QOX-Si-3.0% was as follows: compound (I-1) (X1):E-MA (X2):ITX (X3):DMPA (X4)=3:50:0.5:0.5 (molar ratio). The molar percentage X1 of the compound (I-1) (i.e. QOX-Si) in each photopolymerization system was shown in Table 1. As described above, X2+X3 was fixed to 100 and X2:X3=1:1, and X4 and X5 were kept unchanged.

[0098] QOX-Si: 1 H NMR (400 MHz, Chloroform-d) δ 3.87 (dd, J = 175.8, 12.5 Hz, 16H), 3.51 (d, J = 12.5 Hz, 4H), 3.45 - 3.24 (m, 12H), 1.83 - 1.51 (m, 16H), 0.84 (dt, J = 13.7, 7.4 Hz, 20H), -0.04 (s, 12H).

[0099] Example 2

[0100] The purpose of this example is to illustrate the photopolymerization performance of the compound of the present application. The preparation process of the photocuring composition is as follows:

[0101] The above compound (I-1) (X1 mol), E4221 (3,4-epoxycyclohexylmethyl 3,4- epoxycyclohexylcarboxylate) (X2 mol), VOH (4-vinyl epoxycyclohexane) (X3 mol), photoinitiator diphenyl iodonium hexafluorophosphate (810) (X4 mol) and sensitizer 2-isopropylthioxanthone (ITX) (X5 mol) were weighed into a brown bottle and stirred uniformly, and stored in dark. Taking the photocuring composition QOX-Si-3.0% as an example, the molar ratio of each component was as follows: compound (I-1) (X1):E4221 (X2):VOH (X3):810 (X4):ITX (X5)=3:50:50:1:0.5 (molar ratio). The molar percentage X1 of the compound (I-1) (i.e. QOX-Si) in each photopolymerization system was shown in Table 1. As described above, X2+X3 was fixed to 100 and X2:X3=1:1, and X4 and X5 were kept unchanged.

[0102] A mixture of the photoinitiator diphenyl iodonium hexafluorophosphate (810) and 2-isopropylthioxanthone (ITX, sensitizer) in a 2:1 molar ratio was used as the photoinitiating system. The photopolymerization kinetics of the compound (I-1) was tested by real-time infrared (RT-IR) method (real-time infrared spectrometer: Nicolet 5700, Thermo Electron Corporation, USA) and the effect of the compound (I-1) on the photopolymerization kinetics of the E4221 / VOH system was investigated. The monomers E4221 and VOH used in this experiment have a C-O-C vibration absorption peak at 750 cm -1 The C-O-C vibration absorption peak of the tetraoxa ring of the compound (I-1) used as the polymerizable monomer has a vibration absorption peak at 980 cm -1 The photopolymerizable liquid composed of the monomers and the photoinitiator was uniformly coated on a potassium bromide salt tablet (a little of the photopolymerizable liquid was taken up with a fine tube, dropped on the potassium bromide salt tablet and then uniformly spread), and the liquid sample was irradiated with a high-pressure mercury lamp for 900 s. The mercury lamp mainly emits light at a wavelength of 365 nm and has a light guide fiber with a diameter of 5 mm. The light guide fiber was 10 cm away from the test sample at either end, and the irradiation intensity was 20 mW cm -2 The real-time conversion rate and the polymerization rate of the different epoxy groups, i.e. the monomers, were characterized by measuring the change in the C-O-C bond peak area at 750 cm -1 and 980 cm -1 .

[0103] The results of the photopolymerizable compositions containing the compound (I-1) (i.e. QOX-Si) are shown in Figures 1-2 and Table 1, respectively (in the figures and the table below, QOX-Si-3.0% means that the content of X1 in the formula is 3.0 mol%). The results show that the addition of the compound (I-1) can significantly improve the conversion rate and the conversion rate of the monomers of the E4221 / VOH system. In addition, the compound (I-1) can significantly improve the conversion rate of the alicyclic epoxy group with a small amount of addition (1.5-9 mol%), and the maximum conversion rate is even as high as 69%. Furthermore, it can be seen from Figure 2 that the conversion rate of the compound (I-1) itself is significantly increased. Therefore, the compound of the present application can improve the photopolymerization performance of the monomers of the E4221 / VOH system and the compound of the present application itself has excellent photopolymerization activity.

[0104] Table 1: Conversion rate of monomers at 900 s of the photopolymerizable compositions using the compound (I-1) (QOX-Si)

[0105] Example 3

[0106] The purpose of this example is to illustrate that the compound of the present application can improve the surface hydrophobicity of the photocured film.

[0107] X1 mol of the above compound (I-1) (i.e. QOX-Si), X2 mol of E4221, X3 mol of VOH, X4 mol of photoinitiator diphenyliodonium hexafluorophosphate (810) and X5 mol of sensitizer 2-isopropylthioxanthone (ITX) were weighed into a brown bottle and stirred uniformly, and stored in the dark. The molar ratio of each component in the formula was: monomer (X1): E4221 (X2): VOH (X3): 810 (X4): ITX (X5) = 9 (X1): 50: 50: 1: 0.5. The uniformly stirred photosensitive liquid was added to a 6 mm x 8 mm x 70 mm polytetrafluoroethylene mold, and then the mold was placed under a mercury lamp for irradiation (wavelength 365 nm, light intensity 60 mW cm -2 ), and the cured film was removed after irradiation for 900 s, and water contact angle testing was performed.

[0108] The surface hydrophobicity of the photocured film was characterized using a DSA25 water contact angle tester, and the test temperature was 25°C. At the same time, a blank E4221 / VOH cured film was prepared as a reference using the same method. The results for the reference and in the presence of compound (I-1) are shown in Figure 3.

[0109] As can be seen from Figure 3, when the E4221 / VOH polymerization system does not contain the compound of the present application, the water contact angle of the cured film is 54.3°, and after the addition of compound (I-1), the water contact angle of the cured film is significantly improved. Therefore, the compound of the present application can significantly improve the surface hydrophobicity of the cured film.

[0110] Example 4

[0111] Each of the respective cured films in the presence of compound (I-1) was prepared in exactly the same way as described in Example 3. Then the thermal resistance of each photocured film was determined using a thermogravimetric analyzer (DTG-60AH, Shimadzu Enterprise Management (China) Co., Ltd.). The test conditions were: nitrogen protection, temperature range 25-600°C, and heating rate 10°C / min. At the same time, a blank E4221 / VOH cured film was prepared as a reference using the same method. The results are shown in Table 2 and Figure 4.

[0112] As can be seen from Table 2 and Figure 4, after the addition of compound (I-1), the initial decomposition temperature (T 5％ ) and the maximum thermal weight loss temperature (T max ) of the cured film are significantly improved, and thus the thermal resistance is significantly improved.

[0113] Table 2: Thermogravimetric data for photocured films using compound (I-1) (i.e. QOX-Si)

[0114] Example 5

[0115] The purpose of this example is to demonstrate that the compound of the present application can improve the tensile properties of the photocured film.

[0116] The same method as described in Example 3 was used to prepare the respective cured films in the presence of compound (I-1) respectively. Then the tensile properties of the photocured films were tested by using an electronic universal testing machine (Model E44.304, Metzler-Industrietechnik (China) Co., Ltd.) according to the international standard ISO 1184-1983 "Determination of tensile properties of plastics films". The test temperature was 25°C, the humidity was 60%, and the test speed was 1 mm / min. At the same time, a blank E4221 / VOH cured film was prepared by the same method as a reference. The results are shown in Table 3 and Figure 5.

[0117] As shown in Table 3 and Figure 5, the tensile strength of the pure E4221 / VOH photocured film was 0.96 MPa, and the elongation at break was 6.21%. After the addition of compound (I-1), the tensile strength of the photocured film was significantly improved. Therefore, the compound of the present application can significantly improve the tensile properties of the cured film.

[0118] Table 3: Tensile properties data of photocured films using compound (I-1) (i.e. QOX-Si)

Claims

1. Compound of formula (I): wherein R1, R2, R3, R4are the same or different and independently an organic group having 1 to 12 carbon atoms; R5, R6, R7, R8are the same or different and independently H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; and L1, L2, L3, L4are the same or different and independently a linking group having 2 to 30 carbon atoms.

2. The compound of formula (I) according to claim 1, wherein R1, R2, R3, and R4 are the same or different and are independently C6-C. 10 Aryl, C1-C 12 Alkyl, C1-C 12 Alkyl group, independently selected from NR a C2-C with non-adjacent heteroatoms of O and S 12 Alkyl groups or groups independently selected from NR a C2-C with non-adjacent heteroatoms of O and S 12 alkoxy group, where R a It is H or C1-C4 alkyl.

3. The compound of formula (I) according to claim 1, wherein R1, R2, R3, R4are the same or different and independently C6-C 10 aryl, C1-C6alkyl, C1-C6alkoxy or C2-C6alkyl interrupted by one or more non-adjacent heteroatoms independently selected from NR a , O, S, wherein R a is H or C1-C4alkyl; preferably R1, R2, R3, R4are the same or different and independently phenyl, C1-C4alkyl, C1-C4alkoxy or C2-C4alkyl interrupted by one or more non-adjacent heteroatoms independently selected from NR a , O, S, wherein R a is H or C1-C4alkyl; and / or R5, R6, R7, R8are the same or different and independently H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; and / or L1, L2, L3, L4are the same or different and independently C2-C 10 alkylene or C3-C 10 cycloalkylene.

4. The compound of formula (I) according to claim 1, wherein R1, R2, R3, R4 are the same or different and independently phenyl, C1-C4 alkyl, C1-C4 alkoxy or C2-C4 alkyl interrupted by one or more non-adjacent heteroatoms independently selected from NR a , O, S, wherein R a is H or C1-C4 alkyl; R5, R6, R7, R8 are the same or different and independently H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; and L1, L2, L3, L4 are the same or different and independently C2-C6 alkylene or C4-C8 cycloalkylene; Preferably, R1, R2, R3, R4are the same or different and independently C1-C4 alkyl; R5, R6, R7, R8are the same or different and independently H or C1-C4 alkyl; L1, L2, L3, L4are the same or different and independently C2-C4 alkylene or C5-C6 cycloalkylene.

5. The compound of formula (I) according to claim 1, which is a compound of formula (I-1): ###0002### (I-1) 6. A method for preparing the compound of formula (I) according to any one of claims 1-5, comprising reacting the compound of formula (II) with the compound of formula (III) to obtain the compound of formula (I): wherein R a R5, R6, R7, R8and independently are as defined in any one of claims 1 and 3-5, L is alkenyl or cycloalkenyl having 2-30 carbon atoms, wherein R1, R2, R3and R4are as defined in any one of claims 1 to 5.

7. The process according to claim 6, wherein the reaction of the compound of formula (II) with the compound of formula (III) is carried out in the presence of Karstedt’s catalyst or Speier’s catalyst, preferably the amount of catalyst is 2 to 500 ppm, preferably 80 to 200 ppm, based on the weight of the compound of formula (III); and / or the molar ratio of the compound of formula (II) to the compound of formula (III) is 4:1 to 6:1, preferably 4:1 to 4.5:1; and / or the reaction between the compound of formula (II) and the compound of formula (III) is carried out at 80 to 110 °C, preferably 85 to 100 °C; and / or the reaction between the compound of formula (II) and the compound of formula (III) is carried out for 6 to 20 hours, preferably 10 to 16 hours.

8. A photocurable composition comprising the compound of formula (I) according to any one of claims 1 to 5 as a polymerizable monomer.

9. A photocured material obtained from the photocurable composition according to claim 8.

10. Use of the compound of formula (I) according to any one of claims 1 to 5 in photocured coatings, adhesives, inks and photoresists.

Images