Photocurable silicone composition and its application

Abstract

The present invention provides a photocurable silicone composition and its application. The photocurable silicone composition comprises a photoinitiator and a silicone resin, wherein the photoinitiator comprises at least one of the compounds having the structure shown in Formula I, wherein R 0 It is C 4 ~C 20 Branched alkyl, C 4 ~C 20 Any of the linear alkyl groups of 1 , R 2 Each independently selected from C 1 ~C 4 Any of the alkyl groups, or CR 1 R 2 is a cyclohexane subunit or a cyclopentane subunit, R 3 , R 5 Each is independently C 1 ~C4 alkyl and phenyl, R 4 It is C 1 ~C 4 Alkyl and -SiR 3 R 5 R 6 Any one of R 6 It is C 1 ~C 4 By screening the initiator, it is found that the initiator having the above structural formula I has good solubility in the silicone resin, thereby improving the curing rate and curing thoroughness of the silicone resin.

Description

Technical Field

[0001] The present invention relates to the technical field of photocurable materials, and in particular to a photocurable organic silicon composition and application thereof. Background Art

[0002] Acrylate-modified organosiloxane is the main resin of the release film coating composition, and many documents (e.g., US Pat. No. 6,211,322, US Pat. No. 4,978,726, and US Pat. No. 6,268,404) disclose the combined use of side chain and terminal (meth)acrylate-modified organopolysiloxanes. The purpose of such a mixture is to combine the advantages of the individual components while suppressing the disadvantages. However, particularly on smooth film substrates, the mixture of US Pat. No. 6,268,404 is insufficient in terms of its adhesion and has a poor release effect.

[0003] European patent EP 1276825B discloses at least binary, preferably at least ternary mixtures of (meth)acrylate-modified organopolysiloxanes as anti-adhesive compositions, which differ in particular due to different chain lengths of polydimethylsiloxane units. In order to overcome the problem of insufficient adhesion of these compositions on polymeric plastic carriers, a possible option is to use an adhesion promoter, which can be any desired polymer containing acrylate groups or vinyl ether groups, preferably a mixture of dipentaerythritol pentaacrylate and 1,6-hexanediol diacrylate. This purely organic coating material shows good adhesion to many substrates and can be mixed with (meth)acrylate-modified organopolysiloxanes. However, the low peel force performance and the long-term stability of the peeling effect will be lost.

[0004] Chinese patent CN107109127B discloses a release coating composition of a ternary mixture, which includes a silicon-free ethoxylated acrylate monomer, a polysiloxane with fewer polymerizable groups, and a polysiloxane with more polymerizable groups. The photoinitiator is a general commercial photoinitiator. Specifically, this release coating composition is used to coat paper or film, which is used as a substrate for self-adhesive labels. The coating surface of the label with pressure-sensitive adhesive must be able to withstand the label lamination operation. The adhesion of the self-adhesive label to the backing adhesive must be high enough so that the label will not be separated from the backing adhesive prematurely when the label is distributed. However, on the other hand, the label must be able to be peeled off from the coated backing film without significantly reducing the viscosity of the adhesive. For this reason, the curing of the silicone resin release layer must be particularly thorough, otherwise the silicone resin component may migrate to the adhesive surface and reduce the viscosity.

[0005] Specifically, in order to prepare the film as described above, the usual formula is two or more organosilicon compounds and one or more photoinitiators as described above, which are coated on a plastic, metal or paper mesh material by roller coating and cured by a UV curing machine at an appropriate speed. Preferably, crosslinking is carried out in the presence of a photoinitiator and / or a photosensitizer, such as benzophenone and its derivatives, benzoin derivatives, α-hydroxyalkyl phenone and derivatives, and acylphosphine oxide and its derivatives. However, in fact, general monomers that do not contain organosilicon groups, that is, acrylate monomers such as NPGDA commonly used in the photocuring industry, are difficult to dissolve with acrylate-modified silicone resins. Finding some diluent monomers with good compatibility is urgently needed for the application technology of photocurable silicone compositions.

[0006] A common feature of all the above-mentioned organosilicon compounds and organic compounds is that they undergo free radical polymerization by ultraviolet irradiation within a very short time after the addition of a photoinitiator. In addition, the photoinitiator must also be dissolved in the coating composition in order to obtain sufficient activity during UV curing. Since the matrix of the organosilicon compound is very hydrophobic, the photoinitiator suitable for the organosilicon composition should be selected to be liquid or easily meltable or compatible with the silicone resin matrix.

[0007] Patent US72502048B2 discloses a composition of long-chain alkyl-substituted α-hydroxyphenylisobutyl ketone and organosiloxane, but after testing, the solubility of this initiator in classic silicone oil is only 2.5%, which seriously limits the amount added in the formula; in order to improve the solubility with the organosilicon compound, patent US 5776658 suggests using silicon-modified photoinitiators, especially polymer silicon-based, such photoinitiators include hydroxy ketones, amino ketones, benzoin ethers, benzophenones or thioxanthones. US4356265 also describes a large number of photoinitiators containing organopolysiloxane structures, for example, the solubility of dialkoxyacetophenone in silicone resin is greatly improved after derivatization. US.Pat.No.4507187 discloses a diketone photoinitiator with a silicon group that is easily soluble in organosilicon polymers. US.Pat.No.4587276 introduces a polymer photoinitiator containing a siloxane group. EP-1072326A introduces a surface-active siloxane-modified photoinitiator, which is also a derivative of a hydroxyalkylphenone having the following structure.

[0008]

[0009] However, the disadvantage of this solution is that compared with the increased solubility of organosilicon initiators in silicone resins, the high molar weight of the silicon or siloxane groups in the photoinitiator molecules reduces the molar weight ratio of the photosensitive group in the molecule. In order to compensate for the reduction in the molar weight ratio of the photosensitive group, the concentration of this type of photoinitiator in silicone resin needs to be increased, which increases the formulation cost.

[0010] Patent US4587276 discloses an example of obtaining a silylated photoinitiator by the addition reaction of hydrogen silane with a double bond, and using this as an intermediate to perform an addition reaction with other polymers with ethylene double bonds using silicon hydrogen groups. In this way, through two silicon hydrogen addition reactions, the initiator group is grafted onto the polymer side chain to form a polymerized photoinitiator, which is beneficial to improve the compatibility with silicone resin.

[0011]

[0012] However, the preparation of these compounds undoubtedly requires multiple complex synthetic steps, or one of the raw materials is relatively expensive, making the target products of these inventions difficult to commercialize and unable to be actually used by technicians in the industry.

[0013] Therefore, it is necessary to find a photoinitiator that is easy to synthesize and has good compatibility for the free radical polymerizable organosilicon compound, which is urgently needed by technicians in this industry. Summary of the invention

[0014] The main purpose of the present invention is to provide a photocurable organic silicon composition and its application, so as to solve the problem of poor compatibility between organic silicon resin and initiator in the prior art.

[0015] In order to achieve the above object, according to one aspect of the present invention, there is provided a photocurable silicone composition, comprising a photoinitiator and a silicone resin, wherein the photoinitiator comprises at least one of the compounds having the structure shown in Formula I,

[0016]

[0017] Among them, R0 is C4~C 20 Branched alkyl, C4~C 20 R1 and R2 are each independently selected from any one of C1~C4 alkyl groups, or CR1R2 is a cyclohexane subyl group or a cyclopentane subyl group, R3 and R5 are each independently selected from any one of C1~C4 alkyl groups and phenyl groups, R4 is any one of C1~C4 alkyl groups and -SiR3R5R6, and R6 is any one of C1~C4 alkyl groups.

[0018] Furthermore, the above R0 is C8~C 15Branched alkyl, C8~C 15 Any one of the straight chain alkyl groups.

[0019] Furthermore, the above R0 is C 10 ~C 13 Branched alkyl, C 10 ~C 13 Any one of the straight chain alkyl groups.

[0020] Furthermore, the compound having the structure shown in Formula I is selected from any one of the compounds having the structure shown in Formula II.

[0021]

[0022] Furthermore, the above R1 and R2 are each independently a methyl group, or CR1R2 is a cyclohexane subunit.

[0023] Furthermore, the above R3, R4, and R5 are each independently a methyl group.

[0024] Furthermore, the compound having the structure shown in Formula I is any one or more of the following compounds:

[0025]

[0026] Furthermore, the above-mentioned silicone resin contains at least one free radical polymerizable group, and preferably the free radical polymerizable group in the silicone resin is an acrylate group, and preferably the main body of the silicone resin is polydimethylsiloxane.

[0027] Furthermore, the above-mentioned photocurable silicone composition includes additives, and the additive components are selected from any one or more of fillers, pigments, surfactants, stabilizers, sensitizers, sensitizers, ultraviolet absorbers, antioxidants, antifogging agents, and solvents.

[0028] Furthermore, based on the total weight of the photocurable silicone composition, the weight content of the compound having the structure represented by formula I is 0.1 to 5%.

[0029] According to another aspect of the present invention, there is provided a non-sticky peelable coating comprising any one of the above-mentioned photocurable silicone compositions.

[0030] According to another aspect of the present invention, a non-sticky and removable coating is provided. The non-sticky and removable coating is prepared by using any one of the above-mentioned non-sticky and removable coatings.

[0031] Furthermore, the method for preparing the above-mentioned anti-sticking peelable coating includes: coating the anti-sticking peelable coating on a substrate, curing it by ultraviolet irradiation under inert gas protection or in air to obtain the anti-sticking peelable coating, wherein the ultraviolet light contains at least light in the wavelength range of 200 to 450nm.

[0032] According to another aspect of the present invention, there is provided an organic silicone adhesive comprising any one of the above-mentioned photocurable organic silicone compositions.

[0033] Furthermore, the above-mentioned silicone adhesive is a protective layer of the substrate.

[0034] According to another aspect of the present invention, a product is provided, which includes any one of the above-mentioned photocurable silicone compositions or is cured by any one of the above-mentioned photocurable silicone compositions, and the product is a 3D printing material, a 3D printed object or a silicone adhesive.

[0035] By applying the technical solution of the present invention and screening the initiators, it is found that the initiator having the above structural formula I has good solubility in the silicone resin, thereby improving the curing rate and curing thoroughness of the silicone resin. DETAILED DESCRIPTION

[0036] It should be noted that, in the absence of conflict, the embodiments and features in the embodiments of the present application can be combined with each other. The present invention will be described in detail below in conjunction with the embodiments.

[0037] As analyzed in the background technology of the present application, the compatibility between the initiator and the silicone resin in the prior art is insufficient. In order to solve this problem, the present application provides a photocurable silicone composition and its application.

[0038] In a typical embodiment of the present application, a photocurable silicone composition is provided, comprising a photoinitiator and a silicone resin, wherein the photoinitiator comprises at least one of the compounds having a structure shown in Formula I,

[0039]

[0040] Among them, R0 is C4~C 20 Branched alkyl, C4~C 20 R1 and R2 are each independently selected from any one of C1~C4 alkyl groups, or CR1R2 is a cyclohexane subyl group or a cyclopentane subyl group, R3 and R5 are each independently selected from any one of C1~C4 alkyl groups and phenyl groups, R4 is any one of C1~C4 alkyl groups and -SiR3R5R6, and R6 is any one of C1~C4 alkyl groups.

[0041] The present application screened the initiators and found that the initiator having the above-mentioned general structural formula I has good solubility in the silicone resin, thereby improving the curing rate and curing thoroughness of the silicone resin.

[0042] In some embodiments, preferably R0 is C8~C 15 Branched alkyl, C8~C 15 Any one of the straight chain alkyl groups of 10 ~C 13 Branched alkyl, C 10 ~C 13 Any one of the straight chain alkyl groups.

[0043] In order to further improve the solubility of the initiator in the silicone resin, it is preferred that the compound having the structure shown in Formula I is selected from any one of the compounds having the structure shown in Formula II.

[0044]

[0045] In order to facilitate those skilled in the art to obtain the initiator of formula I of the present application, the preparation method of the initiator is given below, but the following method is only an illustration of a preparation method and does not mean that the initiator must be obtained by the following method. The preparation method includes:

[0046] The compound shown in formula II is used as a raw material, and reacts with trimethylsilyl chloride in the presence of an acid binding agent to obtain an initiator shown in formula I.

[0047]

[0048] Wherein, R0, R1, and R2 in Formula II are defined the same as those in Formula I.

[0049] The acid binding agent is an organic base, such as an organic amine, specifically trimethylamine, triethylamine, tripropylamine, tributylamine, pyridine, 3-methylpyridine, 4-methylpyridine, 4-dimethylaminopyridine, imidazole, 1-methylimidazole, 1-butylimidazole or any mixture thereof.

[0050] In addition to including at least one of the compounds having the structure shown in Formula I, the initiator may also include photoinitiator compounds disclosed in the prior art, α-hydroxyketone photoinitiators include Omnirad 1173 and Esacure KIP150 from IGM Resin Company, benzophenone photoinitiators include benzophenone and Omnirad 991, acylphosphine oxide photoinitiators include Omnirad TPO-L, benzoylformate photoinitiators include Omnirad 754 and Omnirad MBF, etc. As long as they are within the dosage range that is compatible with the resin and stable in storage, they can be used as auxiliary photoinitiators to form the initiator together with the compound shown in Formula I.

[0051] In some embodiments, the initiator with the above general structure is screened, especially when R1 and R2 are each independently a methyl group, or CR1R2 is a cyclohexane subunit, preferably R3, R4, and R5 are each independently a methyl group, the initiator and the silicone resin have better solubility and the initiation ability is more ideal.

[0052] Furthermore, the compound having the structure shown in Formula I can be any one or more of the following compounds:

[0053]

[0054] In order to further promote the crosslinking and curing ability of the silicone resin, the silicone resin preferably contains at least one free radical polymerizable group, preferably the free radical polymerizable group is an acrylate group, and preferably the main chain of the silicone resin is selected from polydimethylsiloxane, such as the silicone resin T2706 of Guangzhou Boxing Company.

[0055] Silicone resins are also available from companies such as Goldschmidt / Germany. RC902, RC1717, X-8010 from Shin Etsu / Japan, UV900, UV911 and UV970 from Rhodia / France; X-22-2445 from Shin-Etsu of Japan.

[0056] In order to improve the film-forming ability of the above-mentioned photocurable silicone composition, in some embodiments, the above-mentioned photocurable silicone composition includes an acrylate monomer, for example, the acrylate monomer is preferably selected from any one or more of isooctyl acrylate, isobornyl acrylate, 1.6-hexanediol diacrylate, trimethylolpropane triacrylate, and silicon-containing acrylate.

[0057] In addition, in order to meet the needs of products with different properties, the above-mentioned photocurable silicone composition may also include additives, and the additive components are selected from any one or more of fillers, pigments, surfactants, stabilizers, sensitizers, sensitizers, ultraviolet absorbers, antioxidants, antifogging agents, and solvents. The specific selection of each of the above-mentioned additives can be selected from the corresponding conventional types in the prior art, and this application will not list them one by one.

[0058] In some embodiments, based on the total weight of the photocurable silicone composition, the weight content of the compound having the structure represented by Formula I is 0.1-5% to provide sufficient initiation ability.

[0059] In another typical embodiment of the present application, a non-stick peelable coating is provided, which contains any of the above-mentioned photocurable silicone compositions. The non-stick peelable coating containing the photocurable silicone composition of the present application has high peelability because the silicone resin and the initiator therein have good compatibility.

[0060] In another typical embodiment of the present application, a non-stick peelable coating is provided, which is prepared by using the above-mentioned non-stick peelable coating. The silicone resin of the non-stick peelable coating can be cured more thoroughly, so the silicone resin will not migrate into the adhesive, thereby maintaining high peelability and ensuring the adhesion of the corresponding adhesive layer.

[0061] In some embodiments, the method for preparing the anti-sticking peelable coating comprises: coating the anti-sticking peelable coating on a substrate, curing it by ultraviolet irradiation under an inert gas protection condition or in air to obtain the anti-sticking peelable coating, wherein the ultraviolet light contains at least light with a wavelength range of 200 to 450 nm. The anti-sticking peelable coating can be obtained by ultraviolet curing, and the method is simple.

[0062] The substrate can be a flexible support of fabric, paper, polyvinyl chloride, polyester, polyethylene, polypropylene, polyamide, polyethylene terephthalate, polyurethane or non-woven fiberglass. These coated substrates have non-stick, water-repellent properties or achieve improved surface properties such as smoothness, anti-fouling or softness.

[0063] Suitable UV radiation sources for curing are medium-pressure mercury vapor lamps, optionally doped or low-pressure mercury vapor lamps, UV-LED lamps or excimer emitters. The UV source can be polychromatic or monochromatic. The emission range of the emitter preferably lies within the absorption range of the photoinitiator and / or photosensitizer.

[0064] In another typical embodiment of the present application, a silicone adhesive having long-term stable adhesion is provided, comprising any one of the above-mentioned photocurable silicone compositions.

[0065] In another typical embodiment of the present application, a product is provided, which includes any one of the above-mentioned photocurable silicone compositions or is cured by any one of the above-mentioned photocurable silicone compositions, and the product is a 3D printing material, a 3D printed object or a silicone adhesive.

[0066] The photocurable silicone composition of the present application can be three-dimensionally crosslinked by free radicals, and under the influence of high-energy radiation such as ultraviolet radiation or electron beams, it can be completely cured in a very short time to form a coating with mechanical and chemical resistance, which has predetermined anti-sticking and peeling properties and adhesion and bonding properties under the appropriate composition of the coating material of the present invention, that is, it has good adhesion on the attached substrate and good peeling force on the protected substrate.

[0067] Photoinitiator Preparation Example 1

[0068] 2-Methyl-2-trimethylsilyloxy-1-(4-C10-13 alkylphenyl)-1-propanone (the actual dodecyl group is C 10-13 Preparation of a mixture of alkylbenzenes

[0069] Step 1: Preparation of 2-methyl-2-bromo-1-(4-C10-13 alkylphenyl)-1-propanone

[0070] Dodecylbenzene (actually C 10-13 24.6 g of alkylbenzene mixture) was dissolved in 100 mL of dichloromethane, and the temperature was lowered to -5°C. 14 g of anhydrous aluminum chloride was added thereto, and the temperature was kept below 0°C. 24 g of 2-bromoisobutyryl bromide was continuously added dropwise thereto. The addition was completed within 30 min, and the mixture was stirred for 2 h. The mixture was acidified and washed with water. The dichloromethane was removed by distillation. The residue was 39.4 g of a light yellow oil.

[0071] Step 2: Preparation of 2-methyl-2-hydroxy-1-(4-C10-13 alkylphenyl)-1-propanone

[0072] The product of the previous step was dissolved in 100 mL of isopropanol and maintained in a water bath at no more than 30° C. 20 g of 30% NaOH solution was added dropwise thereto, and the mixture was stirred for 5 h. Sampling and analysis of the raw material 2-methyl-2-bromo-1-(4-C10-13 alkylphenyl)-1-propanone showed that the content was less than 0.1%. Isopropanol was removed by distillation under reduced pressure, 50 mL of toluene was added, and the mixture was washed with water for several times. The pH value of the aqueous phase was measured to be 7. Distillation under reduced pressure was performed to remove toluene to obtain 32.1 g of a light yellow oil. The total yield of the two steps was 96.7%.

[0073] Step 3: Preparation of 2-methyl-2-trimethylsilyloxy-1-(4-C10-13 alkylphenyl)-1-propanone

[0074] In a 50mL single-mouth bottle, add 6.6g (0.02mol, the second step product of photoinitiator preparation example 1) of 2-methyl-2-hydroxy-1-(4-C10-13 alkylphenyl)-1-propanone, 2.7g (0.022mol) of p-dimethylaminopyridine (DMAP) and 20ml of toluene, stir with electromagnetic, keep warm at 25°C, add 2.35g (0.216mol) of trimethylchlorosilane dropwise, stir for 8h, take a sample and analyze the content of 2-methyl-2-hydroxy-1-(4-C10-13 alkylphenyl)-1-propanone is less than 0.5%, add 20mL of water, separate the deionized water, wash twice with water until the pH value of the aqueous phase is neutral, remove toluene by vacuum distillation, the residue is a light yellow oily liquid, weighing 8g, with a yield of 98.84%. The data proves that it is 2-methyl-2-trimethylsilyloxy-1-(4-C10-13 alkylphenyl)-1-propanone; 1 H-NMR data (CDCl3, ppm): 0.020 (s, 9H, 3CH3), 0.834-0.888 (multiplet, 6.2H, 2CH3), 1.218-1.277 (multiplet, 1 5.1H, CH2), 1.592 (s, 6H, 2CH3), 1.490-1.608 (multiplet, 4.2H, CH2), 2.550-2.778 (multiplet, 1H, CHC6H4).

[0075] Silicone resin:

[0076] B-1: Silicone resin T2706 from Boxing Polymer New Material Technology Co., Ltd.

[0077] Polydimethylsiloxane: trimethylsiloxane end-capped, MW2000, produced by ALFA.

[0078] Testing the solubility in dimethylsiloxane and silicone resin:

[0079] In order to simulate the dissolution in the silicone resin, the photoinitiator product of Preparation Example 1, 2-methyl-2-hydroxy-1-(4-dodecylphenyl)-1-propanone of Preparation Example 1 (control photoinitiator 1), commercial photoinitiator 2-hydroxy-2-methyl-1-phenylpropanone (control photoinitiator 2) of IGM Resin Company, 2-hydroxy-2methyl-1-[4-(2-hydroxyethoxy)phenyl]-1-propanone (control photoinitiator 3) and TPO-L were gradually added to 10 g (accurate to 0.001 g) of polydimethylsiloxane or silicone resin B-1, respectively, in a constant temperature water bath at 20° C. until saturation. The solubility data were measured and recorded in Table 1.

[0080] Table 1

[0081] Solvents 100g dimethicone 100g B-1 Preparation Example 1 Photoinitiator ＞50g ＞50g Control Photoinitiator 1 2.50g 2.62g Control Photoinitiator 2 2.12g 2.2g Control Photoinitiator 3 ＜0.1g ＜0.1g Omnirad TPO-L 1.2g 1.5g

[0082] It can be seen that the solubility of the photoinitiator in silicone oil has been greatly improved after trimethylsilyl etherification, and the solubility has undergone a fundamental change.

[0083] The aforementioned polydimethylsiloxane is a commonly used solvent for testing the solubility of a photoinitiator. Generally, if the solubility in the polydimethylsiloxane is high, it means that the photoinitiator has a high solubility in conventional silicone resins in the art.

[0084] Composition curing test

[0085] The photocurable silicone composition was prepared according to the formula in Table 2.

[0086] Table 2

[0087] Composition formula table Recipe 1 Recipe 2 Recipe 3 Recipe 4 Recipe 5 B-1 96 96 96 Preparation Example 1 Photoinitiator 4 2 2 Control Photoinitiator 1 4 2 Control Photoinitiator 2 4 Omnirad TPO-L 2

[0088] Prepare each composition according to the formula table, add the initiator, heat to 50℃ and stir thoroughly for 30min, cool to 20℃, and keep in a 20℃ heat preservation bath away from light for 2 weeks to observe whether the formula is turbid, whether there is precipitation or even stratification, or whether it is clear and transparent. It is stable if it is clear, uniform, transparent, not stratified, and not turbid. Continue to coat and cure the stable formula composition, and abandon the coating and curing experiment for unstable formula. The curing property is to observe the surface dryness by the finger touch dry method, and the curing property is good if there is no fingerprint.

[0089] The composition was coated onto a cleaned polypropylene plate and cured with a high pressure mercury lamp with an output power of 100 W / cm2. The residual oxygen content was controlled to be less than 50 ppm by nitrogen flow and the conveyor belt speed was 200 m / min. The weight of the silicone resin coating was about 1 g / m2. 2 The surface curing property was observed by the dry-to-touch method. The test results are shown in Table 3.

[0090] Table 3

[0091] formula 1 2 3 4 5 Formula stability Clarify evenly turbid turbid Clarify evenly Clarify evenly Curing No fingerprints Uncoated Uncoated No fingerprints No fingerprints

[0092] Conclusion: The photoinitiator of Preparation Example 1 of the present invention has significantly improved silicone resin compatibility and formulation stability compared to the control photoinitiators, and has good photocuring activity. At the same time, it can also be mixed with other existing photoinitiators and has good solubility.

[0093] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. For those skilled in the art, the present invention may have various modifications and variations. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention shall be included in the protection scope of the present invention.

Claims

1. A photocurable silicone composition comprising a photoinitiator and a silicone resin, characterized in that: The photoinitiator comprises at least one of the compounds having the structure shown in Formula II, in, R0 is C 10 ~C 13 Branched alkyl, C 10 ~C 13 Any of the linear alkyl groups of R1 and R2 are each independently selected from any one of C1 to C4 alkyl groups, or CR1R2 is a cyclohexane subunit or a cyclopentane subunit, R3 and R5 are each independently selected from any one of C1-C4 alkyl and phenyl, R4 is any one of C1-C4 alkyl and -SiR3R5R6, and R6 is any one of C1-C4 alkyl; The organic silicone resin contains at least one free radical polymerizable group; the free radical polymerizable group in the organic silicone resin is an acrylate group, and the main body of the organic silicone resin is polydimethylsiloxane.

2. The photocurable silicone composition according to claim 1, characterized in that: The R1 and R2 are each independently a methyl group, or the CR1R2 is a cyclohexane substituent.

3. The photocurable silicone composition according to claim 2, characterized in that: The R3, the R4, and the R5 are each independently a methyl group.

4. The photocurable silicone composition according to claim 1, characterized in that: The compound having the structure shown in Formula II is any one or more of the following compounds:

5. The photocurable silicone composition according to claim 1 or 4, characterized in that: The photocurable silicone composition includes additives, and the additive components are selected from any one or more of fillers, pigments, surfactants, stabilizers, sensitizers, sensitizers, ultraviolet absorbers, antioxidants, antifogging agents, and solvents.

6. The photocurable silicone composition according to any one of claims 1 to 4, characterized in that Based on the total weight of the photocurable silicone composition, the weight content of the compound having the structure represented by Formula II is 0.1 to 5%.

7. A non-stick peelable coating comprising the photocurable silicone composition according to any one of claims 1 to 6.

8. A non-stick peelable coating, characterized in that: The anti-sticking peelable coating is prepared by using the anti-sticking peelable coating according to claim 7.

9. The non-stick peelable coating according to claim 8, characterized in that The method for preparing the anti-sticking peelable coating comprises: coating the anti-sticking peelable coating on a substrate, curing it by ultraviolet irradiation under inert gas protection or in air to obtain the anti-sticking peelable coating, wherein the ultraviolet light contains at least light with a wavelength range of 200 to 450 nm. 10 . An organosilicon adhesive comprising the photocurable organosilicon composition according to claim 1 .

11. The organic silicon adhesive according to claim 10, characterized in that: The silicone adhesive is a protective layer for the substrate.

12. A product, characterized in that The product comprises the photocurable silicone composition according to any one of claims 1 to 6 or is cured by the photocurable silicone composition according to any one of claims 1 to 6, and the product is a 3D printing material, a 3D printed object or a silicone adhesive.

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