WO2022267989A1 - Monomère oxétane contenant du silicium à base biologique d'eugénol et son procédé de préparation - Google Patents

Monomère oxétane contenant du silicium à base biologique d'eugénol et son procédé de préparation Download PDF

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WO2022267989A1
WO2022267989A1 PCT/CN2022/099400 CN2022099400W WO2022267989A1 WO 2022267989 A1 WO2022267989 A1 WO 2022267989A1 CN 2022099400 W CN2022099400 W CN 2022099400W WO 2022267989 A1 WO2022267989 A1 WO 2022267989A1
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compound
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alkyl
alkylene
alkoxy
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PCT/CN2022/099400
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孙芳
杨宗鑫
邹应全
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湖北固润科技股份有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C07F7/0872—Preparation and treatment thereof
    • C07F7/0876—Reactions involving the formation of bonds to a Si atom of a Si-O-Si sequence other than a bond of the Si-O-Si linkage
    • C07F7/0878—Si-C bond
    • C07F7/0879—Hydrosilylation reactions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups

Definitions

  • the invention relates to the field of photocurable materials, in particular to a eugenol bio-based silicon-containing oxetane monomer.
  • the present invention also relates to a preparation method of the monomer, a photocurable composition comprising the monomer and a photocurable material obtained from the photocurable composition.
  • Photopolymerization technology is the process of using light to initiate the conversion of liquid oligomers or monomers with active substances into solid products. Compared with traditional thermal polymerization technology, photopolymerization can achieve efficient and pollution-free production without using volatile organic solvents, saving a lot of energy. Therefore, photopolymerization technology is regarded as a green process because of its unique low energy consumption requirements, fast curing, solvent-free formula, no pollution, room temperature treatment and environmental protection, so it is widely used in photocuring coatings, adhesives and printing inks. and other fields are widely used.
  • oxetane monomer is a cationic photocuring system.
  • Oxycyclane monomer is the main raw material of high-end cationic photocurable products. This system not only has low viscosity and low toxicity.
  • people have put forward higher requirements for the heat resistance, water repellency, surface anti-staining, corrosion resistance and anti-fingerprint of photo-curing materials. Require. Consumers are increasingly demanding the appearance of products. In addition to beautiful colors and comfortable handles, they also require the surface to have anti-fingerprint and anti-stain properties. was wiped clean.
  • the base material is prepared from the base material, with fast polymerization rate. After photocuring, it has the advantages of good tensile properties, good heat resistance, excellent hydrophobic properties, anti-staining, and anti-fingerprints.
  • the present inventors unexpectedly found that the cationic photopolymerizable eugenol bio-based silicon-containing oxetane monomer of formula (I) of the present invention has good polymerization rate and conversion rate and promotes the synthesis of other cationic monomers. Polymerization, and the photocurable material obtained therefrom has good mechanical properties, especially tensile properties and thermal stability, excellent hydrophobic properties and anti-staining and anti-fingerprints.
  • the monomer has a good polymerization rate and conversion rate and promotes the polymerization of other cationic monomers, and the photocurable material obtained therefrom has good mechanical properties, especially tensile properties and heat resistance, excellent hydrophobic properties, and Stain, anti-fingerprint, anti-chemical corrosion, strong anti-aging performance.
  • Another object of the present invention is to provide a method for preparing the eugenol bio-based silicon-containing oxetane monomer of the present invention.
  • the preparation method is simple and easy, the conditions are mild, the raw materials are readily available and the price is low.
  • Yet another object of the present invention is to provide a photocurable composition comprising the eugenol bio-based silicone-containing oxetane monomer according to the present invention.
  • Another object of the present invention is to provide a photocurable material obtained from the photocurable composition of the present invention.
  • Another object of the present invention is to provide the use of the compound of formula (I) of the present invention in photocurable coatings, adhesives and inks.
  • n 1-50;
  • L is a direct bond or a divalent linking group with 1-30 carbon atoms
  • R 1 , R 2 , R 3 , R 4 , R 5 are the same or different, and are independently organic groups with 1-12 carbon atoms;
  • R 6 is H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy.
  • n 1-30;
  • R 1 is C 1 -C 12 alkyl or C 1 -C 12 alkoxy
  • R 2 , R 3 , R 4 , and R 5 are the same or different, and are independently C 6 -C 10 aryl, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, and are independently represented by one or more C 2 -C 12 alkyl separated by non-adjacent heteroatoms selected from NR a , O, S, or C separated by one or more non-adjacent heteroatoms independently selected from NR a , O, S 2 -C 12 alkoxy, and
  • L is a direct bond, C 1 -C 30 alkylene, C 1 -C 30 alkyleneoxy, C 2 - separated by one or more non-adjacent heteroatoms independently selected from NR a , O, S C 30 alkylene, or C 2 -C 30 alkyleneoxy interrupted by one or more non-adjacent heteroatoms independently selected from NR a , O, S,
  • R a is H or C 1 -C 4 alkyl.
  • - m is 1-20, preferably 2-15;
  • R 1 is C 1 -C 6 alkyl or C 1 -C 6 alkoxy; R 1 is preferably C 1 -C 4 alkyl or C 1 -C 4 alkoxy;
  • R a is H or C 1 -C 4 alkyl; preferably, R 2 , R 3 , R 4 , R 5 , the same or different, and independently phenyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or one or more independently selected from NR a , O, S C 2 -C 4 alkyl interspersed by non-adjacent heteroatoms, wherein R a is H or C 1 -C 4 alkyl;
  • -R 6 is H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy ;
  • -L is C 2 -C 30 alkylene, C 2 -C 30 alkyleneoxy, C 2 -C 30 separated by one or more non-adjacent heteroatoms independently selected from NR a , O, S Alkylene, or C 2 -C 30 alkyleneoxy interrupted by one or more non-adjacent heteroatoms independently selected from NR a , O, S, wherein R a is H or C 1 -C 4 alkane base.
  • n 1-9;
  • R 1 is C 1 -C 4 alkyl or C 1 -C 4 alkoxy
  • R 2 , R 3 , R 4 , and R 5 are the same or different, and are independently phenyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or one or more independently selected from NR a , C 1 -C 4 alkyl separated by non-adjacent heteroatoms of O, S, wherein R a is H or C 1 -C 4 alkyl;
  • R 6 is H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy; as well as
  • L is L 1 -OL 2 , wherein L 1 and L 2 are independently a divalent linking group with 1-20, preferably 1-15 carbon atoms, more preferably C 1 -C 15 alkylene;
  • n 3-9;
  • R 1 is C 1 -C 4 alkyl
  • R 2 , R 3 , R 4 , and R 5 are the same or different, and are independently C 1 -C 4 alkyl;
  • R 6 is H or C 1 -C 4 alkyl
  • L is L 1 -OL 2 , wherein L 1 and L 2 are independently C 1 -C 6 alkylene.
  • L is L 1 -OL 2 , wherein L 1 and L 2 are independently of each other a divalent linking group having 1-20, preferably 1-15 carbon atoms, more preferably C 1 -C 15 alkylene, especially C 1 -C 6 alkylene.
  • L is a divalent linking group having 1-20 , preferably 1-15 carbon atoms, more preferably C 1 -C 15 alkylene, especially C 1 -C 6 alkylene, and X is halogen , such as fluorine, chlorine, bromine or iodine,
  • L 2 is a divalent linking group having 1-20, preferably 1-15 carbon atoms, more preferably a C 1 -C 15 alkylene group, especially a C 1 -C 6 alkylene group, R 6 is as in paragraph as defined in any one of items 1-5, and X is halogen, such as chlorine, bromine or iodine.
  • reaction of the compound of formula (II) with the compound of formula (III) is carried out in the presence of a basic catalyst, preferably sodium hydride, sodium hydroxide, potassium hydroxide, triethylamine, potassium carbonate or any mixture thereof, More preferably, the molar ratio of the compound of formula (II) to the basic catalyst is 1:1-1:5;
  • reaction between the compound of formula (II) and the compound of formula (III) is carried out at 30-120°C, preferably 40-70°C;
  • reaction between the compound of formula (II) and the compound of formula (III) is carried out for 3-16 hours, preferably 4-10 hours.
  • reaction of the compound of formula (IV) with the compound of formula (VI) is carried out in the presence of a basic catalyst, preferably sodium hydride, sodium hydroxide, potassium hydroxide, triethylamine, potassium carbonate or any mixture thereof, More preferably, the molar ratio of the compound of formula (IV) to the basic catalyst is 1:1-1:5;
  • reaction between the compound of formula (IV) and the compound of formula (VI) is carried out at 40-100°C, preferably at 60-90°C; preferably, the reaction is carried out for 3-24 hours, preferably 4-10 hours.
  • reaction of the compound of formula (VI) with the compound of formula (VII) is carried out in the presence of Karstedt catalyst or SpeIer catalyst, preferably, the amount of catalyst is 2-500ppm based on the weight of formula (VII);
  • reaction between the compound of formula (VI) and the compound of formula (VII) is carried out at 80-110°C, preferably 85-100°C;
  • reaction between the compound of formula (VI) and the compound of formula (VII) is carried out for 3-6 hours, preferably 3.5-5.5 hours.
  • a photocurable composition comprising a compound of formula (I) according to any one of items 1-5 as a polymerizable monomer.
  • Fig. 1 is a graph showing the change of E4221 conversion rate with irradiation time in the system containing compound 1 prepared in Example 1.
  • Fig. 2 is a graph showing the change of E4221 conversion rate with irradiation time in the system containing compound 2 prepared in Example 2.
  • Fig. 3 is a graph showing the change of E4221 conversion rate with irradiation time in the system containing compound 3 prepared in Example 3.
  • FIG. 4 is a graph showing the conversion rate of Compound 1 in the system containing Compound 1 prepared in Example 1 as a function of irradiation time.
  • Fig. 5 is a graph of the conversion of compound 2 in the system containing compound 2 prepared in Example 2 as a function of irradiation time.
  • Fig. 6 is a graph showing the conversion of compound 3 in the system containing compound 3 prepared in Example 3 as a function of irradiation time.
  • Fig. 7 is a contact angle graph of a blank E4221 cured film and a cured film of a system comprising compounds 1-3 prepared in each of Examples 1-3.
  • Fig. 8 is a thermogravimetric graph of cured films of blank E4221 and cured films of systems comprising compounds 1-3 prepared in each of Examples 1-3.
  • Fig. 9 is a graph showing the mechanical properties of a blank E4221 cured film and a cured film of a system containing compounds 1-3 prepared in each of Examples 1-3.
  • a numerical range is used to indicate a range in which the numerical values described before and after are taken as the minimum value and the maximum value, respectively.
  • n 1-50;
  • L is a direct bond or a divalent linking group with 1-30 carbon atoms
  • R 1 , R 2 , R 3 , R 4 , R 5 are the same or different, and are independently organic groups with 1-12 carbon atoms;
  • R 6 is H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy.
  • the prefix "C n -C m " indicates in each case that the number of carbon atoms contained in the group is nm.
  • Halogen refers to fluorine, chlorine, bromine and iodine. In the present invention, it is preferred that the halogen includes fluorine, chlorine or a combination thereof.
  • C n -C m alkyl refers to a branched or unbranched saturated hydrocarbon group having nm, such as 1-12, preferably 1-6, particularly preferably 1-4 carbon atoms, such as Methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methyl Butyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2- Dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethyl Dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,
  • the C 1 -C 6 alkyl group may be methyl, ethyl, propyl, isopropyl, n-butyl, 2-butyl, tert-butyl, pentyl, isopentyl, hexyl and isomers thereof.
  • C 1 -C 4 Alkyl can be methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl groups and their isomers.
  • C 6 -C m aryl refers to a monocyclic, bicyclic or multicyclic aromatic hydrocarbon group containing 6-m carbon atoms, for example 6-10 carbon atoms.
  • C 6 -C m aryl groups mention may be made of phenyl, tolyl, ethylphenyl, propylphenyl, butylphenyl, xylyl, methylethylphenyl, diethylphenyl, Methyl-propylphenyl and naphthyl, etc.; preferably phenyl or naphthyl, especially phenyl.
  • C n -C m alkoxy refers to a C n -C m alkyl corresponding to any carbon atom of an open chain C n -C m alkane bonded with an oxygen atom as a linking group C n -C m alkyl, such as C 1 -C 12 alkoxy, more preferably C 1 -C 6 alkoxy, especially preferably C 1 -C 4 alkoxy.
  • C 1 -C 6 alkoxy can be methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, 2-butoxy, tert-butoxy, pentyloxy, isopentyloxy group, hexyloxy group and its isomers.
  • C 1 -C 4 alkoxy can be methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy and its isomers body.
  • C n -C m haloalkyl refers to C n -C m alkyl substituted by one or more same or different halogen atoms, such as C 1 -C 12 haloalkyl, preferably C 1 -C 6 Haloalkyl, particularly preferably C 1 -C 4 haloalkyl.
  • Cn- Cm haloalkyl groups mention may be made of monochloromethyl, monochloroethyl, dichloroethyl, trichloroethyl, monochloropropyl, 1-chloromethylethyl, monochlorobutyl Base, 1-chloromethylpropyl, 2-chloromethylpropyl, 1,1-dichloromethylethyl, 1-chloropentyl, 1-chloromethylbutyl, 2-chloromethylbutyl, 3-chloromethylbutyl, 2,2-dichloromethylpropyl, 1-chloroethylpropyl, monochlorohexyl, 1,1-dichloromethylpropyl, 1,2-dichloromethyl Propyl, 1-chloromethylpentyl, 2-chloromethylpentyl, 3-chloromethylpentyl, 4-chloromethylpentyl, 1,1-dichloromethylbutyl, 1,
  • C n -C m haloalkoxy refers to C n -C m alkoxy substituted by one or more same or different halogen atoms, such as C 1 -C 12 haloalkoxy, more preferably C 1 -C 6 haloalkoxy, especially preferably C 1 -C 4 haloalkoxy.
  • C n -C m haloalkoxy mention may be made of monochloromethoxy, 2-chloroethoxy, 3-chloropropoxy, 2-chloroisopropoxy, 4-chloro-n-butoxy , 3-chloro-sec-butoxy, 2-chloro-tert-butoxy, 5-chloropentyloxy, 4-chloroisoamyloxy, 6-chlorohexyloxy and its isomers.
  • C n -C m hydroxyalkyl refers to a C n -C m that has a hydroxyl group bonded to any carbon atom of an open chain C n -C m alkane corresponding to a C n -C m alkyl group.
  • Alkyl such as C 1 -C 6 hydroxyalkyl, especially preferably C 1 -C 4 hydroxyalkyl, such as hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxyisopropyl, hydroxybutyl, hydroxypentyl, Hydroxyhexyl and its isomers.
  • C 1 -C 30 alkylene as used herein includes C 1 -C 26 alkylene, C 1 -C 18 alkylene, C 1 -C 12 alkylene, C 1 -C 6 alkylene, C 2 -C 26 alkylene, C 2 -C 18 alkylene, C 2 -C 12 alkylene, C 2 -C 6 alkylene, C 3 -C 26 alkylene, C 3 -C 18 alkylene Alkyl, C 3 -C 12 alkylene or C 3 -C 6 alkylene.
  • C 1 -C 30 alkyleneoxy as used herein includes C 1 -C 26 alkyleneoxy, C 1 -C 18 alkyleneoxy, C 1 -C 12 alkyleneoxy, C 1 -C 6 alkylene Alkoxy, C 2 -C 26 Alkyleneoxy, C 2 -C 18 Alkyleneoxy, C 2 -C 12 Alkyleneoxy, C 2 -C 6 Alkyleneoxy, C 3 -C 26 Alkylene Alkoxy, C 3 -C 18 alkyleneoxy, C 3 -C 12 alkyleneoxy or C 3 -C 6 alkyleneoxy.
  • the propylene group between the silicon and the benzene ring in the compound of formula (I) may be -CH 2 -CH 2 -CH 2 - or -CH(CH 3 )-CH 2 -, and is preferably -CH( CH3 ) -CH2- .
  • m is generally 1-50, such as 1-40, 1-30, 1-20, 1-18, 1-15, 1-12, 1-9, 2-40, 2-30, 2- 20, 2-18, 2-15, 2-12, 2-9, 3-40, 3-30, 3-20, 3-18, 3-15, 3-12 or 3-9, such as 3, 4, 5, 6, 7, 8 or 9.
  • R 1 , R 2 , R 3 , R 4 , and R 5 are the same or different, and are independently an organic group with 1-12 carbon atoms, such as an organic group with 1-6 or 1-4 carbon atoms .
  • R 1 is usually C 1 -C 12 alkyl or C 1 -C 12 alkoxy.
  • R 1 is C 1 -C 6 alkyl or C 1 -C 6 alkoxy.
  • R 1 is C 1 -C 4 alkyl or C 1 -C 4 alkoxy.
  • R 1 is C 1 -C 4 alkyl.
  • R 1 is methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl or tert-butyl.
  • R 2 , R 3 , R 4 , and R 5 are the same or different, and are usually independently C 6 -C 10 aryl, C 1 -C 12 alkyl, C 1 -C 12 Alkoxy or C 1 -C 12 alkyl interrupted by one or more non-adjacent heteroatoms independently selected from NR a , O, S, wherein R a is H or C 1 -C 4 alkyl.
  • R 2 , R 3 , R 4 , and R 5 are the same or different, and are independently C 6 -C 10 aryl, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or replaced by one or multiple non-adjacent heteroatom-interrupted C 1 -C 6 alkyl groups independently selected from NR a , O, S, wherein R a is H or C 1 -C 4 alkyl.
  • R 2 , R 3 , R 4 , and R 5 are the same or different, and are independently phenyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or replaced by one or more independently A C 1 -C 4 alkyl group selected from NR a , O, S with non-adjacent heteroatom intervals, wherein R a is H or C 1 -C 4 alkyl.
  • R 2 , R 3 , R 4 , R 5 are the same or different, and are independently C 1 -C 4 alkyl.
  • R 2 , R 3 , R 4 , and R 5 are the same or different, and are independently phenyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, Methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy or tert-butoxy.
  • non-adjacent heteroatom means that there is a non-adjacent heteroatom between two carbon atoms, for example, two carbon atoms of the divalent linking group.
  • an ethylene group interrupted by O can be represented as: -CH2 - O-CH2-.
  • R 6 is usually H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy.
  • R 6 is H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy or C 1 -C 4 Haloalkoxy. It is particularly preferred that R 6 is H or C 1 -C 4 alkyl.
  • R can be H, chloro, bromo, methyl, ethyl, n - propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy , isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, hydroxymethyl, hydroxyethyl, hydroxy-n-propyl, hydroxyisopropyl, hydroxy-n-butyl, hydroxy-sec-butyl or hydroxy tert-butyl.
  • L is a direct bond or a divalent linking group with 1-30 carbon atoms, for example with 1-28, 1-18, 1-12, 2-30, 2-28, 2-18 or 2 - a divalent linking group of 12 carbon atoms, for example a divalent linking group having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms.
  • the divalent linking group has one or more non-adjacent heteroatoms independently selected from NR a , O, S, preferably O, wherein R a is H or C 1 -C 4 alkyl.
  • L is a direct bond, C 1 -C 30 alkylene, C 1 -C 30 alkyleneoxy, non-adjacent by one or more independently selected from NR a , O, S A C 2 -C 30 alkylene group separated by heteroatoms, or a C 2 -C 30 alkylene group separated by one or more non-adjacent heteroatoms independently selected from NR a , O, S, wherein R a is H or C 1 -C 4 alkyl.
  • L is a direct bond, C 1 -C 18 alkylene, C 1 -C 18 alkyleneoxy, non-adjacent by one or more independently selected from NR a , O, S A C 2 -C 18 alkylene group interrupted by heteroatoms, or a C 2 -C 18 alkyleneoxy group separated by one or more non-adjacent heteroatoms independently selected from NR a , O, and S, wherein R a is H or C 1 -C 4 alkyl.
  • L is a direct bond, C 1 -C 12 alkylene, C 1 -C 12 alkyleneoxy, non-adjacent by one or more independently selected from NR a , O, S A C 2 -C 12 alkylene group interrupted by heteroatoms, or a C 2 -C 12 alkyleneoxy group separated by one or more non-adjacent heteroatoms independently selected from NR a , O, S, wherein R a is H or C 1 -C 4 alkyl.
  • L is a direct bond, C 2 -C 12 alkylene, C 2 -C 12 alkyleneoxy, non-adjacent by one or more independently selected from NR a , O, S
  • L is L 1 -OL 2
  • L 1 and L 2 are independently 1-20, preferably 1-15, 1-12, 1-6, 2-20, 2-15, A divalent linking group of 2-12 or 2-6 carbon atoms.
  • L 1 and L 2 independently of each other are C 1 -C 15 alkylene, preferably C 1 -C 10 alkylene, preferably C 1 -C 6 alkylene, such as methylene, ethylene, propylene group, butylene, pentylene or hexylene.
  • L 1 is C 1 -C 6 alkylene, preferably C 2 -C 6 alkylene and L 2 is C 1 -C 6 alkylene, preferably C 1 -C 4 alkylene.
  • the propylene group between the silicon and the benzene ring in the compound of formula (I) is -CH 2 -CH 2 -CH 2 - or -CH(CH 3 )-CH 2 -, preferably is -CH(CH 3 )-CH 2 -.
  • each variable in the compound of formula (I) is defined as follows:
  • n 1-30;
  • L is a direct bond or a divalent linking group with 1-12 carbon atoms
  • R 1 , R 2 , R 3 , R 4 , R 5 are the same or different, and are independently organic groups with 1-6 carbon atoms;
  • R 6 is H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy.
  • each variable in the compound of formula (I) is defined as follows:
  • n 1-15;
  • L is a direct bond or a divalent linking group with 1-12 carbon atoms
  • R 1 , R 2 , R 3 , R 4 , R 5 are the same or different, and are independently organic groups with 1-6 carbon atoms;
  • R 6 is H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy.
  • each variable in the compound of formula (I) is defined as follows:
  • n 1-30;
  • R 1 is C 1 -C 12 alkyl or C 1 -C 12 alkoxy
  • R 2 , R 3 , R 4 , and R 5 are the same or different, and are independently C 6 -C 10 aryl, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, and are independently represented by one or more C 2 -C 12 alkyl separated by non-adjacent heteroatoms selected from NR a , O, S, or C separated by one or more non-adjacent heteroatoms independently selected from NR a , O, S 2 -C 12 alkoxy, and
  • L is a direct bond, C 1 -C 30 alkylene, C 1 -C 30 alkyleneoxy, C 2 - separated by one or more non-adjacent heteroatoms independently selected from NR a , O, S C 30 alkylene, or C 2 -C 30 alkyleneoxy interrupted by one or more non-adjacent heteroatoms independently selected from NR a , O, S,
  • R a is H or C 1 -C 4 alkyl.
  • the compound of formula (I) of the present invention satisfies at least one of the following definitions, preferably all:
  • - m is 1-20, preferably 2-15;
  • R 1 is C 1 -C 6 alkyl or C 1 -C 6 alkoxy; R 1 is preferably C 1 -C 4 alkyl or C 1 -C 4 alkoxy;
  • R a is H or C 1 -C 4 alkyl; preferably, R 2 , R 3 , R 4 , R 5 , the same or different, and independently phenyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or one or more independently selected from NR a , O, S C 2 -C 4 alkyl interspersed by non-adjacent heteroatoms, wherein R a is H or C 1 -C 4 alkyl;
  • -R 6 is H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy ;
  • -L is C 2 -C 30 alkylene, C 2 -C 30 alkyleneoxy, C 2 -C 30 separated by one or more non-adjacent heteroatoms independently selected from NR a , O, S Alkylene, or C 2 -C 30 alkyleneoxy interrupted by one or more non-adjacent heteroatoms independently selected from NR a , O, S, wherein R a is H or C 1 -C 4 alkane base.
  • n 1-20;
  • R 1 is C 1 -C 12 alkyl or C 1 -C 12 alkoxy
  • R 2 , R 3 , R 4 , and R 5 are the same or different, and are independently C 6 -C 10 aryl, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, and are independently represented by one or more C 2 -C 12 alkyl separated by non-adjacent heteroatoms selected from NR a , O, S, or C separated by one or more non-adjacent heteroatoms independently selected from NR a , O, S 2 -C 12 alkoxy, wherein R a is H or C 1 -C 4 alkyl, and
  • L is a direct bond, C 1 -C 30 alkylene, C 1 -C 30 alkyleneoxy, C 2 - separated by one or more non-adjacent heteroatoms independently selected from NR a , O, S C 30 alkylene, or C 2 -C 30 alkyleneoxy interrupted by one or more non-adjacent heteroatoms independently selected from NR a , O, S, wherein R a is H or C 1 -C 4 alkyl.
  • each variable in the compound of formula (I) has the following definitions:
  • n 1-9;
  • R 1 is C 1 -C 4 alkyl or C 1 -C 4 alkoxy
  • R 2 , R 3 , R 4 , and R 5 are the same or different, and are independently phenyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or one or more independently selected from NR a , C 1 -C 4 alkyl separated by non-adjacent heteroatoms of O, S, wherein R a is H or C 1 -C 4 alkyl;
  • R 6 is H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy; as well as
  • L is L 1 -OL 2 , wherein L 1 and L 2 are independently a divalent linking group having 1-20, preferably 1-15 carbon atoms, more preferably C 1 -C 15 alkylene.
  • n 1-12;
  • R 1 is C 1 -C 4 alkyl or C 1 -C 4 alkoxy
  • R 2 , R 3 , R 4 , and R 5 are the same or different, and are independently phenyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or one or more independently selected from NR a , C 1 -C 4 alkyl separated by non-adjacent heteroatoms of O, S, wherein R a is H or C 1 -C 4 alkyl;
  • R 6 is H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy; as well as
  • L is L 1 -OL 2 , wherein L 1 and L 2 are independently C 1 -C 15 alkylene.
  • n 3-9;
  • R 1 is C 1 -C 4 alkyl
  • R 2 , R 3 , R 4 , and R 5 are the same or different, and are independently C 1 -C 4 alkyl;
  • R 6 is H or C 1 -C 4 alkyl, especially H or ethyl, and
  • L is L 1 -OL 2 , wherein L 1 and L 2 are independently C 1 -C 6 alkylene.
  • the compound of formula (I) is one or more compounds selected from the group consisting of:
  • L in the compound of formula (I) is L 1 -OL 2 , wherein L 1 and L 2 are as defined above, preferably C 1 -C 15 alkylene, more preferably C 1 -C 6 alkylene.
  • the compound of formula (VI) can be prepared by the following steps:
  • L is a divalent linking group having 1-20 , preferably 1-15 carbon atoms, more preferably C 1 -C 15 alkylene, especially C 1 -C 6 alkylene, and X is halogen, such as fluorine, chlorine, bromine or iodine,
  • L 2 is a divalent linking group having 1-20, preferably 1-15 carbon atoms, more preferably a C 1 -C 15 alkylene group, especially a C 1 -C 6 alkylene group and R 6 is as above for the formula (I)
  • X is halogen such as chlorine, bromine or iodine.
  • step (1) the reaction of the phenolic hydroxyl group in the compound of formula (II) with the halogen in the compound of formula (III) belongs to the type of reaction known in the art, and the reaction produces hydrogen halide.
  • the reaction is carried out in the presence of a basic catalyst.
  • basic catalysts suitable for this reaction mention may be made of sodium hydride, sodium hydroxide, potassium hydroxide, triethylamine, potassium carbonate or any mixture thereof.
  • the amount of catalyst used is also conventional.
  • the molar ratio of the compound of formula (II) to the basic catalyst is 1:1-1:5, preferably 1:1-1:3.
  • the reaction of the compound of formula (II) with the compound of formula (III) is usually carried out in a solvent.
  • the solvent is also conducive to the precipitation of the product, that is, the compound of formula (IV).
  • an organic solvent is usually used, preferably toluene, acetone, methyl ethyl ketone, toluene, tetrahydrofuran, cyclohexane, 1,4-dioxane, dichloromethane, acetonitrile or any mixture thereof.
  • the amount of solvent used is also conventional, generally speaking, the amount of solvent used is 1.0-3 times the total weight of the compound of formula (II) and compound of formula (III).
  • the compound of formula (II) and the compound of formula (III) are usually used in approximately equimolar amounts.
  • the molar ratio of the compound of formula (II) to that of formula (III) is 1:0.75-1:1.5, or 1:1-1:1.3.
  • the compound of formula (II) is usually dissolved in a solvent, a basic catalyst is added, and then the compound of formula (III) is added. After the addition is complete, the resulting reaction mixture is stirred evenly, and then the temperature is raised to 30-120° C., preferably to 40-70°C.
  • the reaction is usually continued for 3-16 hours, preferably for 4-10 hours. Of course, the reaction is advantageously carried out with stirring.
  • the compound of formula (IV) can be obtained through conventional post-treatment.
  • the post-treatment usually includes extraction or washing (such as washing with water, after which water-absorbing compounds such as magnesium sulfate or sodium sulfate are advantageously used to remove water), filtration or centrifugation to remove solid impurities, rotary evaporation to remove solvents, and vacuum distillation to further remove solvents. If a higher purity product is to be obtained, the product can also be obtained by recrystallization or column chromatography.
  • step (2) the reaction of the terminal hydroxyl group in the compound of formula (IV) with the halogen in the compound of formula (V) is known to produce hydrogen halide.
  • the reaction is carried out in the presence of a catalyst.
  • a catalyst As suitable catalysts for this reaction, mention may be made of sodium hydride, sodium hydroxide, potassium hydroxide, triethylamine, potassium carbonate or any mixture thereof.
  • the amount of catalyst used is also conventional.
  • the molar ratio of the compound of formula (IV) to the catalyst is 1:1-1:5, preferably 1:1-1:3.
  • the reaction of the compound of formula (IV) with the compound of formula (V) is usually carried out in a solvent.
  • the type of solvent there is no special limitation, as long as the compound of formula (IV), compound of formula (V) and corresponding catalyst can be dissolved and do not participate in the reaction between the compound of formula (IV) and compound of formula (V), preferably
  • the solvent also facilitates the precipitation of the product, namely the compound of formula (VI).
  • an organic solvent is usually used, preferably toluene, acetone, methyl ethyl ketone, toluene, tetrahydrofuran, cyclohexane, 1,4-dioxane, dichloromethane, acetonitrile or any mixture thereof.
  • the amount of solvent used is also conventional, generally speaking, the amount of solvent used is 1.0-3 times the total weight of the compound of formula (IV) and compound of formula (V).
  • the compound of formula (IV) and the compound of formula (V) are usually used in approximately equimolar amounts.
  • the molar ratio of the compound of formula (IV) to the compound of formula (IV) is 1:0.75-1:1.5, or 1:1-1:1.2.
  • the compound of formula (IV) and the catalyst are usually dissolved in a solvent, and then the solution of the compound of formula (V) in the solvent is added. After the addition, the temperature is raised to 40-100° C., preferably to 60-90° C.
  • the reaction is usually continued for 3-24 hours, preferably for 4-10 hours. Of course, the reaction is advantageously carried out with stirring.
  • the compound of formula (VI) can be obtained through conventional post-treatment.
  • the post-treatment usually includes extraction or washing (such as washing with water, after which water-absorbing compounds such as magnesium sulfate or sodium sulfate are advantageously used to remove water), filtration or centrifugation to remove solid impurities, rotary evaporation to remove solvents, and vacuum distillation to further remove solvents. If a higher purity product is to be obtained, impurities can also be separated by recrystallization or column chromatography.
  • the silicon atom of the compound of formula (VII) contains hydrogen atoms, therefore, the compound of formula (VII) can be called hydrogen-containing silicone oil.
  • Addition reactions of silicon-bonded hydrogen atoms in compounds of formula (VII) to unsaturated carbon-carbon double bonds in compounds of formula (VI) are of the type known in the art.
  • the reaction is carried out in the presence of a catalyst.
  • a catalyst suitable for this reaction a Karstedt catalyst or a Speier catalyst is generally used.
  • the amount of catalyst used is also conventional.
  • the catalyst is used in an amount of 2-500 ppm, preferably 10-300 ppm.
  • the reaction of the compound of formula (VI) with the compound of formula (VII) is usually carried out in a solvent.
  • a solvent As the type of solvent, there is no particular limitation, as long as the compound of formula (VI), the compound of formula (VII) and the catalyst can be dissolved and it does not participate in the reaction between the compound of formula (VI) and the compound of formula (VII).
  • the solvent also facilitates the precipitation of the product, the compound of formula (I).
  • an organic solvent is usually used, preferably petroleum ether, dichloromethane, toluene, xylene or any mixture thereof.
  • the amount of solvent used is also conventional, generally speaking, the amount of solvent used is 1.5-3 times the total weight of the compound of formula (VI) and compound of formula (VII).
  • the compound of formula (VI) and the compound of formula (VII) are usually used in approximately equimolar amounts.
  • the molar ratio of the compound of formula (VI) to the compound of formula (VII) is 1:0.75-1:1.5.
  • the compound of formula (VI) and the catalyst are usually dissolved in a solvent and aged for a period of time, then contacted with the compound of formula (VII), and then heated to the reaction temperature for a period of time to obtain the compound of formula (I). Aging is usually carried out at elevated temperature, usually at 40-70°C. The aging time is usually 30-60 minutes.
  • the reaction temperature between the compound of formula (VI) and the compound of formula (VII) is usually 80-110°C, preferably 85-100°C.
  • the holding time of the reaction between the compound of formula (VI) and the compound of formula (VII) at the reaction temperature is usually 3-6 hours, preferably 3.5-5.5 hours.
  • the reaction is advantageously carried out with stirring.
  • the product of the compound of formula (I) can be obtained through conventional post-treatment.
  • the post-treatment usually includes filtration or centrifugation to remove solid impurities, rotary evaporation to remove solvent, and vacuum distillation to further remove solvent. If a higher purity product is to be obtained, it can also be recrystallized.
  • the compound of formula (I) of the present invention is a cationic photocurable monomer, which has fast polymerization rate, high conversion rate and can promote the polymerization of other cationic monomers.
  • the photocurable material obtained after photocuring polymerization has mechanical properties, especially tensile properties. Good, excellent hydrophobic performance, anti-stain, anti-fingerprint, anti-chemical corrosion, strong anti-aging performance, good heat resistance.
  • a photocurable composition comprising the compound of formula (I) of the present invention as a polymerizable monomer.
  • the photocurable composition may also contain a cationic photoinitiator for ring-opening polymerization (a photoinitiator capable of initiating cationic polymerization) and optionally other photoinitiators containing cationic photocurable groups Groups such as vinyl ether double bonds, alicyclic epoxy, oxiranyl or oxetanyl monomers, oligomers, such as 3,4-epoxycyclohexylmethyl3,4- Epoxycyclohexyl carboxylate (E4221).
  • a cationic photoinitiator for ring-opening polymerization a photoinitiator capable of initiating cationic polymerization
  • other photoinitiators containing cationic photocurable groups Groups such as vinyl ether double bonds, alicyclic epoxy, oxiranyl or oxetanyl monomers, oli
  • the amount of the compound of formula (I) of the present invention may be at least 0.5 mol%, at least 1 mol%, at least 2 mol%, for example 0.5-12 mol%, based on the total amount of polymerized monomers, Or 0.5-10mol%, or 1-10mol%.
  • the photocurable composition of the present invention may be a photocurable coating composition, a photocurable ink composition, a photoresist composition, and the like. After the composition is cured, the obtained cured product has good tensile properties, excellent hydrophobic properties, stain resistance, fingerprint resistance, chemical corrosion resistance and strong aging resistance.
  • iodonium salts and sulfonium salts are commonly used.
  • the iodonium salt photoinitiator and the sulfonium salt photoinitiator have the following general formulas (A) and (B) respectively
  • R a , R b , R c , R d , R e are each independently unsubstituted C 6 -C 10 aryl, or are selected from halogen, nitro, carbonyl, C 1 -C 12 alkyl, C 1 C 6 -C 10 aryl substituted by substituents of -C 12 alkoxy, phenylthio, phenyl and substituted phenyl, preferably phenyl or naphthyl, or selected from halogen, nitro, C 1 - C 6 alkyl and substituted phenyl or naphthyl substituted by substituents of phenyl, wherein the substituted phenyl contains one or more substituents selected from halogen, nitro, C 1 -C 6 alkyl and C 1 -C 6 alkoxy radicals; and
  • Y and Z are non-nucleophilic anions, such as trifluoromethanesulfonate, BF 4 - , ClO 4 - , PF 6 - , AsF 6 - , SbF 6 - .
  • a photoinitiator one or more selected from the group consisting of 4-(phenylthio)phenyl diphenylsulfonium hexafluorophosphate, 4-(phenylthio)phenyl ⁇ Diphenylsulfonium hexafluoroantimonate, bis(4-(diphenylsulfonium)phenyl)sulfide bishexafluorophosphate, bis(4-(diphenylsulfonium)phenyl)sulfide bishexafluorophosphate Fluoroantimonate, 10-(4-biphenyl)-2-isopropylthioxanthone-10-sulfonium hexafluorophosphate, 10-(4-biphenyl)-2-isopropylthioxanthone Keto-10-sulfonium hexafluoroantimonate, diphenyliodonium hexafluoroantimonate
  • the photocurable composition of the present invention may also contain a sensitizer.
  • a sensitizer mention may be made, for example, of 2-isopropylthioxanthone.
  • the amount of photoinitiator used is conventional. Based on the total molar amount of polymerized monomers in the photocurable composition of the present invention, the content of the photoinitiator is generally 0.5-5 mol%, preferably 1-3 mol%.
  • a photocurable material obtained from the photocurable composition of the present invention is obtained by photocuring the photocurable composition of the invention.
  • the light-curing material has good mechanical properties, especially tensile properties, excellent hydrophobic properties, and has the advantages of anti-staining, anti-fingerprint, anti-chemical corrosion, strong anti-aging performance and good heat resistance.
  • the compounds of formula (I) according to the invention can also be used in photocurable coatings, adhesives, inks and photoresists. Accordingly, the present invention also relates to the use of compounds of formula (I) in photocurable coatings, adhesives, inks and photoresists.
  • the purpose of this example is to illustrate the photopolymerizable properties of the compounds of the present invention.
  • the preparation process of photocurable composition is as follows:
  • the preparation method of the photocurable composition containing compound 2-3 is consistent with that of compound 1.
  • X 1 of the compounds 1, 2 and 3 of the present invention ie Eugenol-Si 3 , Eugenol-Si 6 and Eugenol-Si 9
  • Table 1-3 The mole percentage X 1 of the compounds 1, 2 and 3 of the present invention (ie Eugenol-Si 3 , Eugenol-Si 6 and Eugenol-Si 9 ) in each photocomposition is shown in Table 1-3 below, and X 1 +X 2 as mentioned above Fixed at 100, X 3 and X 4 remain the same.
  • a mixture of photoinitiator diphenyliodonium hexafluorophosphate (810) and 2-isopropylthioxanthone (ITX, sensitizer) in a molar ratio of 2:1 was used as the photoinitiation system, and real-time infrared
  • the (RT-IR) method was used to test the photopolymerization kinetics of compounds 1-3, and to investigate the effects of each of them on the photopolymerization performance of E4221 at different contents.
  • the vibration absorption peak of the COC of the three-membered oxygen heterocycle of the monomer E4221 used is located at 750 cm -1
  • the vibration absorption peak of the COC of the four-membered oxygen heterocycle of compound 1-3 as a polymerized monomer is 980 cm -1 .
  • the photocurable liquid composed of the precursor and the photoinitiator is evenly spread on the potassium bromide salt sheet (take a little photocurable liquid with a thin tube, click it on the potassium bromide salt sheet, and then spread it evenly), and irradiate it with a high-pressure mercury lamp Liquid sample 900s, in which the main emission wavelength of the mercury lamp is 365nm, and it has an optical fiber with a diameter of 5mm.
  • the distance between one end of the optical fiber and the test sample is 10cm, and the radiation intensity is 20mW cm - 2 .
  • the purpose of this example is to illustrate that the compound of the present invention can improve the surface hydrophobicity of the photocured film.
  • a water contact angle test was performed.
  • the surface hydrophobicity of the photocured film was characterized by a DSA25 water contact angle measuring instrument, and the test temperature was 25°C. At the same time, use the same method to prepare a blank E4221 cured film as a reference. The results for reference and compounds 1-3 are shown in Figure 7.
  • the respective cured films of compounds 1-3 were prepared in exactly the same manner as described in Example 6. Then, the heat resistance of each photocured film was measured using a thermogravimetric analyzer (DTG-60AH Shimadzu Enterprise Management (China) Co., Ltd.). The test conditions are: under nitrogen protection, the temperature range is 25-700°C, and the heating rate is 10°C/min. At the same time, use the same method to prepare a blank E4221 cured film as a reference. The results are shown in Figure 8 and Table 4.
  • the initial decomposition temperature (T 5% ) and the maximum thermal weight loss temperature of the cured film are the decomposition temperature (T max1 ) and the first stage of the fastest weight loss.
  • the decomposition temperature (T max2 ) is obviously increased when the weight loss is the fastest in the second stage, so the heat resistance is obviously improved.
  • the purpose of this example is to illustrate that the compounds of the present invention can improve the tensile properties of photocured films.
  • the respective cured films of compounds 1-3 were prepared in exactly the same manner as described in Example 6. Then, the electronic universal testing machine (E44.304, Meters Industrial Systems (China) Co., Ltd.) was used to test the tensile properties of the light-cured film according to the international standard ISO 1184-1983 "Determination of Tensile Properties of Plastic Films". The test temperature is 25°C, the humidity is 60%, and the test speed is 1mm/min. At the same time, use the same method to prepare a blank E4221 cured film as a reference. The results are shown in Figure 9 and Table 5.
  • E44.304 Meters Industrial Systems (China) Co., Ltd.
  • the tensile strength of the pure E4221 light-cured film is 6.10 MPa, and the elongation at break is 1.7%.
  • the tensile strength and elongation at break of the light-cured film gradually increased after the addition of compound 1-3 monomers.
  • the compounds of the present invention are able to significantly improve the tensile properties of cured films.

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Abstract

La présente invention concerne un monomère oxétane contenant du silicium à base biologique d'eugénol, un procédé de préparation du monomère, une composition photodurcissable contenant le monomère, et un matériau photodurcissable préparé à partir de la composition photodurcissable. Le monomère oxétane contenant du silicium à base biologique d'eugénol selon la présente invention est bon en termes de vitesse de polymérisation et de taux de conversion et favorise la polymérisation d'autres monomères cationiques ; de plus, le matériau photodurcissable préparé à partir de celui-ci a de bonnes propriétés mécaniques et une bonne stabilité thermique, d'excellentes propriétés hydrophobes, et est résistant aux taches et résistant aux empreintes digitales.
PCT/CN2022/099400 2021-06-21 2022-06-17 Monomère oxétane contenant du silicium à base biologique d'eugénol et son procédé de préparation WO2022267989A1 (fr)

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