阅读说明：本技术 一种异氰酸酯改性的uv单体及其制备方法 (Isocyanate modified UV monomer and preparation method thereof ) 是由 熊东路 易松 杨轩 龙绪俭 徐涛 肖增钧 鲁晓东 李斌仁 于 2020-05-09 设计创作，主要内容包括：本发明涉及UV涂料技术领域,具体涉及一种异氰酸酯改性的UV单体<Image he="240" wi="538" file="DDA0002484351100000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>所述R<Sub>1</Sub>、R<Sub>2</Sub>分别独立含有以下X、Y、Z结构中的任一种,<Image he="87" wi="700" file="DDA0002484351100000012.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>其中,所述p＝2,n、m分别独立为1-20的自然数,所述L<Sub>1</Sub>、L<Sub>2</Sub>、L<Sub>3</Sub>分别独立为氢或甲基。本发明异氰酸酯改性的UV单体作为UV树脂和聚氨酯树脂的桥梁,具有色浅、固化速度快、硬度高、低成本等优异性能,又能解决丙烯酸UV树脂涂膜收缩大、附着力差、耐冲击性差、韧性差等弊病；同时还具有高度耐热性和耐久性,能形成具有高挠曲性、力学性能优异的高分子膜。(The invention relates to the technical field of UV (ultraviolet) coatings, in particular to an isocyanate modified UV monomer The R is 1 、R 2 Each independently having any one of the following X, Y, Z structures, wherein p is 2, n and m are natural numbers of 1-20 respectively, and L is 1 、L 2 、L 3 Each independently hydrogen or methyl. The isocyanate modified UV monomer is used as a bridge of UV resin and polyurethane resin, has excellent performances of light color, high curing speed, high hardness, low cost and the like, and can solve the problem of acrylic resinThe olefine acid UV resin has the defects of large film shrinkage, poor adhesive force, poor impact resistance, poor toughness and the like; meanwhile, the composite material has high heat resistance and durability, and can form a high-polymer film with high flexibility and excellent mechanical properties.)

1. A method for preparing an isocyanate-modified UV monomer, comprising the steps of: monitoring the reaction end point by measuring an NCO value and a hydroxyl value under the action of a catalyst by using an acrylate monomer with hydroxyl and a diisocyanate group compound to obtain the isocyanate modified UV monomer;

the structure of the acrylate monomer with hydroxyl is as follows:the R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein n, m and p are respectively independent natural numbers more than or equal to 1; said L₁、L₂、L₃Each independently is any one of hydrogen, saturated aliphatic alkyl, unsaturated aliphatic alkyl, aromatic alkyl, cycloalkyl, saturated aliphatic alkyl substituted by other elements, unsaturated aliphatic alkyl substituted by other elements, aromatic alkyl substituted by other elements and cycloalkyl substituted by other elements; the other elements are selected from fluorine, chlorine, bromine,Any one of iodine, sulfur, phosphorus, oxygen, and nitrogen.

2. The method according to claim 1, wherein the diisocyanate group-containing compound is at least one selected from the group consisting of isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, methylene bis (4-cyclohexyl diisocyanate), trimethylhexamethylene diisocyanate, toluene-2, 4-diisocyanate, and methylene diphenyl-4, 4' -diisocyanate.

3. The method according to claim 1, wherein the ratio of the amounts of the hydroxyl group-containing acrylate monomer and diisocyanate group-containing compound is (0.9 to 1.3): 1.

4. the method according to any one of claims 1 to 3, wherein the catalyst is one or more selected from stannous octoate, dibutyltin dichloride and dibutyltin dilaurate.

5. An isocyanate-modified UV monomer prepared according to the preparation method of any one of claims 1 to 4, wherein the isocyanate-modified UV monomer has a structure of:the R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein n, m and p are respectively independent natural numbers more than or equal to 1; said L₁、L₂、L₃Each independently is any one of hydrogen, saturated aliphatic alkyl, unsaturated aliphatic alkyl, aromatic alkyl, cycloalkyl, saturated aliphatic alkyl substituted by other elements, unsaturated aliphatic alkyl substituted by other elements, aromatic alkyl substituted by other elements and cycloalkyl substituted by other elements; the other elements are selected from fluorine, chlorine, bromine, iodine,Sulfur, phosphorus, oxygen, nitrogen.

6. The isocyanate-modified UV monomer of claim 5, wherein n, m, and p are each independently a natural number from 1 to 20.

7. The isocyanate-modified UV monomer of claim 5, wherein p is 2; and n and m are respectively independent natural numbers of 3-12.

8. The isocyanate-modified UV monomer of any one of claims 5 to 7, wherein the saturated aliphatic alkyl group is a straight chain alkyl group having 1 to 10 carbon atoms.

9. The isocyanate-modified UV monomer of claim 8, wherein R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein n and m are respectively independent natural numbers of 3-12; said L₁、L₂、L₃Each independently hydrogen or methyl.

10. The isocyanate-modified UV monomer of claim 9, wherein the isocyanate-modified UV monomer comprises isocyanate-modified UV monomer W1, W1 formulaWherein R is₁₁＝R₂₁，R₁₁Is represented by the structural formulaOr isocyanate modified UV monomer W2 with W2 structural formula as shown inWherein R is₁₂＝R₂₂，R₁₂Is represented by the structural formulaOr isocyanate modified UV monomer W3 with W3 structural formula as shown inWherein R is₁₃＝R₂₃，R₁₃Is represented by the structural formulaOr isocyanate modified UV monomer W4 with W4 structural formula as shown inWherein R is₁₄、R₂₄The structural formula is shown asThe isocyanate modified UV monomer W5 has a structural formula of W5Wherein R is₁₅、R₂₅The structural formula is shown asOr isocyanate modified UV monomer W6 with W6 structural formula as shown inWherein R is₁₆、R₂₆The structural formula is shown asOr isocyanate modified UV monomer W7 with W7 structural formula as shown inWherein R is₁₇、R₂₇The structural formula is shown asAny one of the above.

Technical Field

The invention relates to the technical field of UV coatings, in particular to an isocyanate modified UV monomer and a preparation method thereof.

Background

Acrylic UV resin is widely applied to various UV coating systems due to its excellent properties of light color, high curing speed, high hardness, low cost and the like, but simultaneously causes the defects of large shrinkage of a coating film, poor adhesion, poor impact resistance, poor toughness and the like. The addition of a proper amount of polyurethane UV resin is one of the solutions, and the polyurethane UV resin has good wear resistance, excellent adhesion and adjustable hardness, but the price of the resin is relatively high, and particularly, the practical application of the resin is restricted by products of foreign companies. Bonding UV resins and polyurethane resins together requires ties or bridges, which are generally monomers that make the two resins compatible.

For example: the above-mentioned small-molecule monomers developed by Showa Denko K.K. contain both acrylate and isocyanate groups, by which acrylate photosensitive double bonds can be introduced into polyurethane resins, or isocyanate groups can be introduced into polyacrylate resins for use in UV paints or adhesives (the monomers represented by the above-mentioned I and II), but the cost of the above-mentioned monomers is still high, up to 400 RMB/kg. Scientists also synthesize a small molecular monomer (such as the compound with the formula III) with one NCO and one acrylate by using isophorone diisocyanate and hydroxyethyl (meth) acrylate as raw materials, but hydroxyethyl (meth) acrylate is monofunctional, III prepared by the method is not a multifunctional monomer, the crosslinking density is low, and the mechanical property of the formed polymer film is poor. Therefore, the present invention is in need of research on an isocyanate-modified UV monomer that can solve the disadvantages of large film shrinkage, poor adhesion, poor impact resistance, poor toughness, etc., and can form a polymer film with low cost, high crosslinking density, and excellent mechanical properties.

Disclosure of Invention

In order to solve the above technical problems, a first aspect of the present invention provides a method for preparing an isocyanate-modified UV monomer, comprising the steps of: monitoring the reaction end point by measuring an NCO value and a hydroxyl value under the action of a catalyst by using an acrylate monomer with hydroxyl and a diisocyanate group compound to obtain the isocyanate modified UV monomer;

the structure of the acrylate monomer with hydroxyl is as follows:the R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein n, m and p are respectively independent natural numbers more than or equal to 1; said L₁、L₂、L₃Each independently is any one of hydrogen, saturated aliphatic alkyl, unsaturated aliphatic alkyl, aromatic alkyl, cycloalkyl, saturated aliphatic alkyl substituted by other elements, unsaturated aliphatic alkyl substituted by other elements, aromatic alkyl substituted by other elements and cycloalkyl substituted by other elements; the other element is selected from any one of fluorine, chlorine, bromine, iodine, sulfur, phosphorus, oxygen and nitrogen.

In a preferred embodiment, the diisocyanate group compound is at least one selected from the group consisting of isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, methylene bis (4-cyclohexyl diisocyanate), trimethylhexamethylene diisocyanate, toluene-2, 4-diisocyanate, and methylene diphenyl-4, 4' -diisocyanate.

In a preferred embodiment, the ratio of the amounts of the hydroxyl group-containing acrylate monomer and diisocyanate group-containing compound is (0.9 to 1.3): 1.

as a preferable technical scheme, the catalyst is selected from one or more of stannous octoate, dibutyltin dichloride and dibutyltin dilaurate.

In a second aspect, the present invention provides an isocyanate modified UV monomer prepared by the above preparation method, wherein the isocyanate modified UV monomer has a structure of:the R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein n, m and p are respectively independent natural numbers more than or equal to 1; said L₁、L₂、L₃Each independently is any one of hydrogen, saturated aliphatic alkyl, unsaturated aliphatic alkyl, aromatic alkyl, cycloalkyl, saturated aliphatic alkyl substituted by other elements, unsaturated aliphatic alkyl substituted by other elements, aromatic alkyl substituted by other elements and cycloalkyl substituted by other elements; the other element is selected from any one of fluorine, chlorine, bromine, iodine, sulfur, phosphorus, oxygen and nitrogen.

As a preferable technical scheme, n, m and p are respectively independent natural numbers of 1-20.

As a preferred embodiment, p ═ 2; and n and m are respectively independent natural numbers of 3-12.

In a preferred embodiment, the saturated aliphatic alkyl group is a linear alkyl group having 1 to 10 carbon atoms.

As a preferred technical scheme, the R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein n and m are respectively independent natural numbers of 3-12; said L₁、L₂、L₃Each independently hydrogen or methyl.

As a preferable technical scheme, the isocyanate modified UV monomer comprises isocyanate modified UV monomer W1, and the structural formula of W1 is shown asWherein R is₁₁＝R₂₁，R₁₁Is represented by the structural formulaOr isocyanate modified UV monomer W2 with W2 structural formula as shown inWherein R is₁₂＝R₂₂，R₁₂Is represented by the structural formulaOr isocyanate modified UV monomer W3 with W3 structural formula as shown inWherein R is₁₃＝R₂₃，R₁₃Is represented by the structural formulaOr isocyanate modified UV monomer W4 with W4 structural formula as shown inWherein R is₁₄、R₂₄The structural formula is shown asThe isocyanate modified UV monomer W5 has a structural formula of W5Wherein R is₁₅、R₂₅The structural formula is shown asOr isocyanate modified UV monomer W6 with W6 structural formula as shown inWherein R is₁₆、R₂₆The structural formula is shown asOr isocyanate modified UV monomer W7 with W7 structural formula as shown inWherein R is₁₇、R₂₇The structural formula is shown asAny one of the above.

In a third aspect the present invention provides the use of an isocyanate modified UV monomer as described above to render the UV resin and polyurethane resin compatible.

Has the advantages that: the isocyanate modified UV monomer provided by the invention is synthesized by one-step method of acrylate monomer with hydroxyl and isophorone diisocyanate, and has the advantages of simple synthesis method, low cost, definite structure and the like; the isocyanate modified UV monomer prepared by the invention is an acrylic ester monomer with multiple functionality degree containing NCO, can combine UV resin and polyurethane resin together, has good compatibility, excellent performances of light color, high curing speed, high hardness, low cost and the like, and can effectively solve the defects of large shrinkage, poor adhesion, poor impact resistance, poor toughness and the like of acrylic UV resin coating; meanwhile, the composite material has high heat resistance and durability, and can form a high-polymer film with high flexibility and excellent mechanical properties.

Detailed Description

The technical features of the technical solutions provided by the present invention are further clearly and completely described below with reference to the specific embodiments, and the scope of protection is not limited thereto.

The words "preferred", "more preferred", and the like, in the present invention refer to embodiments of the invention that may provide certain benefits, under certain circumstances. However, other embodiments may be preferred, under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, nor is it intended to exclude other embodiments from the scope of the invention.

In order to solve the above technical problems, a first aspect of the present invention provides a method for preparing an isocyanate-modified UV monomer, comprising the steps of: and (2) under the action of a catalyst, monitoring the reaction end point by measuring an NCO value and a hydroxyl value of an acrylate monomer with hydroxyl and a diisocyanate group compound to obtain the isocyanate modified UV monomer.

Acrylate monomer with hydroxyl

In one embodiment, the hydroxyl-bearing acrylate monomer has the structure:the R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein n, m and p are respectively independent natural numbers more than or equal to 1; said L₁、L₂、L₃Each independently is any one of hydrogen, saturated aliphatic alkyl, unsaturated aliphatic alkyl, aromatic alkyl, cycloalkyl, saturated aliphatic alkyl substituted by other elements, unsaturated aliphatic alkyl substituted by other elements, aromatic alkyl substituted by other elements and cycloalkyl substituted by other elements; the other element is selected from any one of fluorine, chlorine, bromine, iodine, sulfur, phosphorus, oxygen and nitrogen.

In one embodiment, the hydroxyl-containing acrylate monomer may be represented by the formula

A. B, C, D, E, F structure:any one of (a); said X₂Represents R₁、R₂Are all X structures; said Y is₂Represents R₁、R₂Are all Y structures; z is₂Represents R₁、R₂Are all Z structures; XY represents R₁、R₂One is an X structure and the other is a Y structure; the XZ represents R₁、R₂One is an X structure and the other is a Z structure; the YZ represents R₁、R₂One is a Y structure and the other is a Z structure; the structural formula of X, Y, Z is:wherein n, m and p are respectively independent natural numbers more than or equal to 1; said L₁、L₂、L₃Each independently is any one of hydrogen, saturated aliphatic alkyl, unsaturated aliphatic alkyl, aromatic alkyl, cycloalkyl, saturated aliphatic alkyl substituted by other elements, unsaturated aliphatic alkyl substituted by other elements, aromatic alkyl substituted by other elements and cycloalkyl substituted by other elements; the other element is selected from any one of fluorine, chlorine, bromine, iodine, sulfur, phosphorus, oxygen and nitrogen.

In a preferred embodiment, R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein n, m and p are respectively independent natural numbers of 1-20; said L₁、L₂、L₃Independently represent hydrogen, saturated aliphatic alkyl, unsaturated aliphatic alkyl, aromatic alkyl, cycloalkyl, saturated aliphatic alkyl substituted by other elements, unsaturated aliphatic alkyl substituted by other elements, aromatic alkyl substituted by other elements, cycloalkyl substituted by other elementsEither one of them; the other element is selected from any one of fluorine, chlorine, bromine, iodine, sulfur, phosphorus, oxygen and nitrogen.

In a preferred embodiment, R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein p is 2, and n and m are respectively independent natural numbers of 3-12; said L₁、L₂、L₃Each independently is any one of hydrogen, saturated aliphatic alkyl, unsaturated aliphatic alkyl, aromatic alkyl and cycloalkyl.

In a preferred embodiment, said L is₁、L₂、L₃Each independently is hydrogen or saturated aliphatic alkyl; the saturated aliphatic alkyl is a straight-chain alkyl group having 1 to 10 carbon atoms.

In a preferred embodiment, the linear alkyl group having 1 to 10 carbon atoms is a methyl group.

In a preferred embodiment, said L is₁、L₂、L₃Each independently hydrogen or methyl.

In a more preferred embodiment, the hydroxyl-containing acrylate monomer is selected from the group consisting of hydroxyl-containing acrylate monomer M1, M1 is represented by the structural formulaWherein R is₁₁＝R₂₁，R₁₁Is represented by the structural formulaOr acrylate monomer M2 with hydroxyl, M2 structural formula is shown asWherein R is₁₂＝R₂₂，R₁₂Is represented by the structural formulaOr with hydroxyl groupsThe acrylate monomer M3, M3 is represented by the structural formulaWherein R is₁₃＝R₂₃，R₁₃Is represented by the structural formulaOr acrylate monomer M4 with hydroxyl, M4 structural formula is shown asWherein R is₁₄、R₂₄The structural formula is shown asOr acrylate monomer M5 with hydroxyl, M5 structural formula is shown asWherein R is₁₅、R₂₅The structural formula is shown asOr acrylate monomer M6 with hydroxyl, M6 structural formula is shown asWherein R is₁₆、R₂₆The structural formula is shown asOr acrylate monomer M7 with hydroxyl, M7 structural formula is shown asWherein R is₁₇、R₂₇The structural formula is shown asOne or more of (a).

In a most preferred embodiment, the hydroxyl-bearing acrylate monomer is a hydroxyl-bearing acrylate monomerThe acrylate monomer M1, M1 is represented by the structural formulaWherein R is₁₁＝R₂₁，R₁₁Is represented by the structural formulaOr acrylate monomer M2 with hydroxyl, M2 structural formula is shown asWherein R is₁₂＝R₂₂，R₁₂Is represented by the structural formula

Diisocyanate based compounds

In one embodiment, the diisocyanate group-containing compound is at least one selected from the group consisting of isophorone diisocyanate, 1, 6-hexamethylene diisocyanate, methylene bis (4-cyclohexyl diisocyanate), trimethylhexamethylene diisocyanate, toluene-2, 4-diisocyanate, and methylene diphenyl-4, 4' -diisocyanate.

In a preferred embodiment, the compound of the diisocyanate group is isophorone diisocyanate.

In one embodiment, the ratio of the amounts of the hydroxyl-bearing acrylate monomer, diisocyanate-based compound, and the like is (0.9 to 1.3): 1.

in a preferred embodiment, the ratio of the amounts of the hydroxyl-containing acrylate monomer and diisocyanate group-containing compound is 1.1: 1.

the ratio of the amount of the hydroxyl group-containing acrylate monomer to the amount of the diisocyanate group-containing compound is 1.1: 1, the reactivity can be remarkably improved, and side reactions caused by further reaction of diisocyanate groups can be avoided.

Catalyst and process for preparing same

In one embodiment, the catalyst is selected from one or more of stannous octoate, dibutyltin dichloride, dibutyltin dilaurate.

In a preferred embodiment, the catalyst is dibutyltin dilaurate.

In one embodiment, the mass of the catalyst is 0.01% to 1% of the total mass of the reactants; preferably, the mass of the catalyst is 0.03-0.05% of the total mass of the reactants.

When the amount of dibutyltin dilaurate exceeds 0.1% of the total mass of the reactants, the reaction is too fast, which results in the formation of byproducts, and the isocyanate-modified UV monomer is not uniform, which easily results in the decrease of the strength, adhesive strength and heat resistance of the formed polymer film; and when the mass of dibutyltin dilaurate is less than 0.01% of the total mass of the reactants, the reaction rate decreases.

In one embodiment, the reaction temperature of the hydroxyl-containing acrylate monomer and the diisocyanate group-containing compound is 30 to 60 ℃; preferably, the reaction temperature of the hydroxyl-containing acrylate monomer and the diisocyanate group-containing compound is 40 to 50 ℃; more preferably, the reaction temperature of the hydroxyl group-containing acrylate monomer and the diisocyanate group-containing compound is 45 to 50 ℃.

When the reaction temperature is too high, the reaction rate is very high, and the acrylate monomer with the hydroxyl group reacts with another NCO in isophorone diisocyanate to generate a byproduct.

In a preferred embodiment, the method for preparing the isocyanate-modified UV monomer comprises the steps of: under the condition of introducing nitrogen for protection, adding isophorone diisocyanate and dibutyltin dilaurate into a four-neck round-bottom flask equipped with a stirring device, raising the temperature to 40 ℃, slowly dropwise adding an acrylate monomer with hydroxyl into the four-neck flask, controlling the temperature to be 45-50 ℃, and monitoring the reaction end point by measuring an NCO value and a hydroxyl value to obtain the isocyanate modified UV monomer.

In a second aspect, the present invention provides an isocyanate modified UV monomer prepared by the above preparation method, wherein the isocyanate modified UV monomer has a structure of:the R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein n, m and p are respectively independent natural numbers more than or equal to 1; said L₁、L₂、L₃Each independently is any one of hydrogen, saturated aliphatic alkyl, unsaturated aliphatic alkyl, aromatic alkyl, cycloalkyl, saturated aliphatic alkyl substituted by other elements, unsaturated aliphatic alkyl substituted by other elements, aromatic alkyl substituted by other elements and cycloalkyl substituted by other elements; the other element is selected from any one of fluorine, chlorine, bromine, iodine, sulfur, phosphorus, oxygen and nitrogen.

In a preferred embodiment, R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein n, m and p are respectively independent natural numbers of 1-20; said L₁、L₂、L₃Each independently is any one of hydrogen, saturated aliphatic alkyl, unsaturated aliphatic alkyl, aromatic alkyl, cycloalkyl, saturated aliphatic alkyl substituted by other elements, unsaturated aliphatic alkyl substituted by other elements, aromatic alkyl substituted by other elements and cycloalkyl substituted by other elements; the other element is selected from any one of fluorine, chlorine, bromine, iodine, sulfur, phosphorus, oxygen and nitrogen.

In a preferred embodiment, R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein p is 2; n and m are respectively independent natural numbers of 1-20; said L₁、L₂、L₃Each independently is any one of hydrogen, saturated aliphatic alkyl, unsaturated aliphatic alkyl, aromatic alkyl and cycloalkyl.

In a preferred embodiment, said L is₁、L₂、L₃Each independently hydrogen or saturated aliphatic alkyl.

In a preferred embodiment, the saturated aliphatic alkyl group is a straight-chain alkyl group having 1 to 10 carbon atoms; preferably, the saturated fatty alkyl group is a methyl group.

In a preferred embodiment, said L is₁、L₂、L₃Each independently hydrogen or methyl.

In a preferred embodiment, R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein p is 2; n and m are respectively independent natural numbers of 3-12; said L₁、L₂、L₃Each independently hydrogen or methyl.

In a preferred embodiment, n and m are each independently any one of 3, 4, 6, 10 and 12.

In a more preferred embodiment, the isocyanate-modified UV monomer comprises isocyanate-modified UV monomer W1, W1 formula is shown asWherein R is₁₁＝R₂₁，R₁₁Is represented by the structural formulaOr isocyanate modified UV monomer W2 with W2 structural formula as shown inWherein R is₁₂＝R₂₂，R₁₂Is represented by the structural formulaOr isocyanate modified UV monomer W3 with W3 structural formula as shown inWherein R is₁₃＝R₂₃，R₁₃Is represented by the structural formulaOr isocyanate modified UV monomer W4 with W4 structural formula as shown inWherein R is₁₄、R₂₄The structural formula is shown asThe isocyanate modified UV monomer W5 has a structural formula of W5Wherein R is₁₅、R₂₅The structural formula is shown asOr isocyanate modified UV monomer W6 with W6 structural formula as shown inWherein R is₁₆、R₂₆The structural formula is shown asOr isocyanate modified UV monomer W7 with W7 structural formula as shown inWherein R is₁₇、R₂₇The structural formula is shown asAny one of the above.

In a most preferred embodiment, the isocyanate-modified UV monomer is isocyanate-modified UV monomer W1, and W1 is represented by the structural formulaWherein R is₁₁＝R₂₁，R₁₁Is represented by the structural formulaOr isocyanate modified UV monomer W2 with W2 structural formula as shown inWherein R is₁₂＝R₂₂，R₁₂Is represented by the structural formula

The inventor unexpectedly discovers in the research process that the isocyanate modified UV monomer prepared from the acrylate monomer with hydroxyl and isophorone diisocyanate can combine UV resin and polyurethane resin together, has the excellent performances of light color, high curing speed, high hardness, low cost and the like, and can effectively solve the defects of large shrinkage, poor adhesion, poor impact resistance, poor toughness and the like of acrylic UV resin coating films. The reason the inventors consider may be that the isocyanate modified UV monomer prepared by the present invention can introduce acrylate photosensitive double bonds into polyurethane resin or isocyanate groups into polyacrylate resin for UV coating or adhesive, and is cheap and low-cost compared with polyurethane UV resin, and suitable for industrial mass production, because the isocyanate modified UV monomer prepared by the present invention includes both acrylate functional groups capable of being used in UV and NCO functional groups of polyurethane. Furthermore, the inventors have surprisingly found that when the hydroxyl-containing acrylate monomer isThe R is₁、R₂Each independently having any one of the following X, Y, Z structures,wherein p is 2, n and m are respectively independent natural numbers of 1-20, and L is₁、L₂、L₃Isocyanate-modified UV monomers prepared with isophorone diisocyanate when each is independently hydrogen or methylThe isocyanate modified UV monomer prepared by the invention is an acrylate monomer with multiple functions containing NCO, has higher crosslinking density, and forms a high polymer film with high flexibility; and the acrylate monomer with hydroxylThe ratio of the amounts of the diisocyanato compounds is 1.1: 1, the mass of dibutyltin dilaurate accounts for 0.01-1% of the total mass of reactants, the reaction temperature is 45-50 ℃, the generation of byproducts can be inhibited, and the method has the advantages of simple synthesis, low cost, clear structure and the like; multifunctional acrylate monomer with hydroxylEnsures that the acrylic UV resin curing product has certain flexibility, maintains relatively low shrinkage rate, is influenced by the structure of monoethanolamine, increases the activity of hydroxyl, ensures that molecules are not easy to tangle, and synthesizes the isocyanate modified UV monomer with definite structure

In a third aspect the present invention provides the use of an isocyanate modified UV monomer as described above to render the UV resin and polyurethane resin compatible.

The present invention will be specifically described below by way of examples. It should be noted that the following examples are only for illustrating the present invention and should not be construed as limiting the scope of the present invention, and that the insubstantial modifications and adaptations of the present invention by those skilled in the art based on the above disclosure are still within the scope of the present invention.

In addition, the starting materials used are all commercially available, unless otherwise specified.