Photocuring pressure-sensitive adhesive as well as preparation method and application thereof

Abstract

The invention provides a photocuring pressure-sensitive adhesive as well as a preparation method and application thereof, and belongs to the technical field of pressure-sensitive adhesives for waterproof materials. The light-cured pressure-sensitive adhesive is prepared from the following raw materials: allyl diethylene glycol dicarbonate, a cationic functional monomer, cationic polymerization type resin, hydroxyethyl acrylamide, a photoinitiator and an organic solvent. The preparation method comprises the following steps: mixing a polymeric monomer and a photoinitiator in an organic solvent, and carrying out photocuring under ultraviolet irradiation to obtain the photocuring pressure-sensitive adhesive. A waterproof coiled material prepared from the light-cured pressure-sensitive adhesive has high adhesive force and excellent retention force, the heat resistance of the light-cured pressure-sensitive adhesive is excellent, and the service life of the pressure-sensitive adhesive in the waterproof coiled material can be prolonged.

Description

Technical Field

[0001] The invention relates to the technical field of pressure-sensitive adhesives for waterproof materials, and in particular to a light-curing pressure-sensitive adhesive and a preparation method and application thereof. Background Art

[0002] Waterproof membrane is mainly used for building walls, roofs, tunnels, roads, landfills, etc. It is a flexible building material product that can be rolled into a roll to resist the seepage of external rainwater and groundwater. As a leak-free connection between the project foundation and the building, it is the first barrier to waterproofing the entire project and plays a vital role in the entire project.

[0003] During the use of waterproof membranes, pressure-sensitive adhesive is required to connect the upper and lower materials of the waterproof membrane to ensure the integrity of the waterproof membrane.

[0004] Existing pressure-sensitive adhesives are divided into hot-melt pressure-sensitive adhesives and light-curing pressure-sensitive adhesives. Hot-melt pressure-sensitive adhesives are mostly made of SBS or SIS thermoplastic rubbers, which contain unsaturated double bonds. Under the long-term action of oxygen and ultraviolet light in the air, they are prone to aging and cross-linking, causing the pressure-sensitive adhesive to lose its viscosity. The polymerized monomers used in light-curing pressure-sensitive adhesives mostly do not contain ultraviolet light-curing functional groups, so the light-curing efficiency is low and it is difficult to exert the performance of the pressure-sensitive adhesive.

[0005] Therefore, how to prepare a photocurable pressure-sensitive adhesive with high photocuring efficiency and long service life and a preparation method thereof are technical problems that need to be solved at present. Summary of the invention

[0006] The object of the present invention is to provide a photocurable pressure-sensitive adhesive and a preparation method thereof, so as to solve the technical problems of low photocuring efficiency and short service life of the existing photocurable pressure-sensitive adhesive.

[0007] In order to achieve the above-mentioned object of the invention, the present invention provides the following technical solutions:

[0008] The present invention provides a light-curable pressure-sensitive adhesive, which is prepared from raw materials containing the following parts by mass:

[0009]

[0010]

[0011] Furthermore, the cationic functional monomer comprises one or more of dimethyldiallylammonium chloride, diallylamine hydrochloride, methacryloyloxyethyltrimethylammonium chloride, diallylamine and oxetane.

[0012] Furthermore, the cationic polymerizable resin comprises 3,4-epoxycyclohexylmethyl and / or 3,4-epoxycyclohexylcarboxylate.

[0013] Furthermore, the photoinitiator comprises a free radical polymerization initiator, a cationic polymerization initiator and benzoyl peroxide, and the mass ratio of the free radical polymerization initiator, the cationic polymerization initiator and the benzoyl peroxide is 1-3:1-3:0.2-05.

[0014] Further, the free radical polymerization initiator comprises one or more of 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-1,2-diphenylethyl-1-ketone, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propane-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinylphenyl)butanone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinylpropane-1-one and 2-hydroxy-2-methyl-1-phenylpropane-1-one.

[0015] Furthermore, the cationic polymerization initiator comprises diphenyl-(4-phenylthio)phenylsulfonium hexafluorophosphate and / or 4-isobutylphenyl-4'-methylphenyliodonium hexafluorophosphate.

[0016] Furthermore, the organic solvent comprises one or more of ethylene glycol dimethyl ether, ethylene glycol butyl ether, diethyl ether and diisoamyl ether.

[0017] The present invention also provides a method for preparing a light-curable pressure-sensitive adhesive, comprising the following steps:

[0018] 1) mixing allyl diglycol dicarbonate, a cationic functional monomer, a cationic polymerizable resin and hydroxyethyl acrylamide in an organic solvent to obtain a mixture;

[0019] 2) mixing the mixture with a free radical polymerization initiator, introducing a protective gas into the mixture, and obtaining a copolymer under continuous ultraviolet irradiation;

[0020] 3) Mixing the copolymer, the cationic polymerization initiator and benzoyl peroxide under heating conditions to finally obtain a light-curable pressure-sensitive adhesive.

[0021] Furthermore, in the step 1), the mixing is carried out under heating conditions, and the heating temperature is 60 to 90° C.;

[0022] In step 2), the ultraviolet irradiation conditions are: irradiation dose 70 to 90 mW·cm -2 , irradiate for 20 to 40 seconds, the peak wavelength of ultraviolet light is 340 to 400 nm;

[0023] In the step 3), the heating temperature is 120-150°C.

[0024] The invention also provides an application of the light-curing pressure-sensitive adhesive in waterproof coiled material.

[0025] Beneficial effects of the present invention:

[0026] The present invention adopts cationic functional monomers and cationic polymerizable resins to cooperate with each other to overcome the influence of air oxygen inhibition on the free radical light-curing pressure-sensitive adhesive, and the allyl group in the allyl diglycol dicarbonate adopted in the present invention can be initiated by ultraviolet light to initiate free radical polymerization reaction, thereby improving the photocuring efficiency and curing speed, and also improving the adhesion of the photocuring pressure-sensitive adhesive.

[0027] The invention adopts hydroxyethyl acrylamide to significantly improve the heat resistance of the light-cured pressure-sensitive adhesive, further improve the anti-oxidation performance of the pressure-sensitive adhesive, and extend the service life of the pressure-sensitive adhesive.

[0028] The invention overcomes the shortcoming that the curable thickness of the free radical light-curing pressure-sensitive adhesive is less than 200 microns, and better meets the requirement of the polymer roll material adhesive layer thickness> 250 microns stipulated in GB / T 23457 "Pre-laid / wet-laid waterproof roll materials" of my country. DETAILED DESCRIPTION

[0029] The present invention provides a light-curable pressure-sensitive adhesive, which is prepared from raw materials containing the following parts by mass:

[0030]

[0031] In the present invention, the content of the allyl diglycol dicarbonate is preferably 35 to 85 parts by mass, more preferably 40 to 80 parts, and even more preferably 50 to 60 parts.

[0032] In the present invention, the content of the cationic functional monomer is preferably 5 to 15 parts by weight, more preferably 8 to 12 parts, and even more preferably 10 parts.

[0033] In the present invention, the content of the cationic polymerizable resin is preferably 10 to 40 parts by mass, more preferably 20 to 30 parts, and even more preferably 22 to 28 parts.

[0034] In the present invention, the content of the hydroxyethyl acrylamide is preferably 1 to 4 parts by mass, and more preferably 2 to 3 parts by mass.

[0035] In the present invention, the content of the photoinitiator is preferably 5 to 25 parts by mass, and more preferably 10 to 20 parts by mass.

[0036] In the present invention, the content of the organic solvent is preferably 50 to 150 parts by mass, and more preferably 60 to 120 parts by mass.

[0037] In the present invention, the cationic functional monomer comprises one or more of dimethyldiallylammonium chloride, diallylamine hydrochloride, methacryloyloxyethyltrimethylammonium chloride, diallylamine and oxetane, preferably dimethyldiallylammonium chloride and / or oxetane.

[0038] In the present invention, the cationic polymerizable resin comprises 3,4-epoxycyclohexylmethyl and / or 3,4-epoxycyclohexylcarboxylate, preferably 3,4-epoxycyclohexylmethyl.

[0039] In the present invention, the photoinitiator comprises a free radical polymerization initiator, a cationic polymerization initiator and benzoyl peroxide, and the mass ratio of the free radical polymerization initiator, the cationic polymerization initiator and benzoyl peroxide is 1-3:1-3:0.2-0.5, preferably 1.5-2.5:1.5-2.5:0.3-0.4.

[0040] In the present invention, the free radical polymerization initiator comprises 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-1,2-diphenyl ethyl-1-ketone, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propane-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinylphenyl)butanone, 2-methyl-1-[4-( One or more of the group consisting of 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-1,2-diphenylethyl-1-one, bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide and 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propane-1-one.

[0041] In the present invention, the cationic polymerization initiator comprises diphenyl-(4-phenylthio)phenylsulfonium hexafluorophosphate and / or 4-isobutylphenyl-4′-methylphenyliodonium hexafluorophosphate, preferably diphenyl-(4-phenylthio)phenylsulfonium hexafluorophosphate.

[0042] In the present invention, the organic solvent comprises one or more of ethylene glycol dimethyl ether, ethylene glycol butyl ether, ethyl ether and diisoamyl ether, preferably ethylene glycol dimethyl ether.

[0043] The present invention also provides a method for preparing a light-curable pressure-sensitive adhesive, comprising the following steps:

[0044] 1) mixing allyl diglycol dicarbonate, a cationic functional monomer, a cationic polymerizable resin and hydroxyethyl acrylamide in an organic solvent to obtain a mixture;

[0045] 2) mixing the mixture with a free radical polymerization initiator, introducing a protective gas into the mixture, and obtaining a copolymer under continuous ultraviolet irradiation;

[0046] 3) Mixing the copolymer, the cationic polymerization initiator and benzoyl peroxide under heating conditions to finally obtain a light-curable pressure-sensitive adhesive.

[0047] In the present invention, in the step 1), the mixing is performed under heating conditions, and the heating temperature is 60 to 90°C, preferably 65 to 85°C, and more preferably 70 to 80°C.

[0048] In the present invention, in step 2), the ultraviolet irradiation conditions are: irradiation dose 70 to 90 mW·cm -2 , irradiation for 20 to 40 seconds, the peak wavelength of ultraviolet light is 340 to 400 nm; preferably, the irradiation dose is 75 to 85 mW·cm -2 , irradiation for 25 to 35 seconds, the peak wavelength of ultraviolet light is 350 to 400 nm; further preferably, the irradiation dose is 80 to 82 mW·cm -2 , irradiate for 28 to 30 seconds, the peak wavelength of ultraviolet light is 350 to 380nm.

[0049] In the present invention, in the step 3), the heating temperature is 120-150°C, preferably 130-140°C, and more preferably 135°C.

[0050] The invention also provides an application of the light-curing pressure-sensitive adhesive in waterproof coiled material.

[0051] In the present invention, the method for applying the light-curing pressure-sensitive adhesive to the waterproof roll is: the light-curing pressure-sensitive adhesive is evenly coated on the polymer waterproof roll by hot-melt coating, and then cured by ultraviolet light.

[0052] In the present invention, the polymer waterproof membrane comprises one or more of a polymer homogeneous sheet, a composite sheet, and a special-shaped sheet, preferably one or more of an EPDM waterproof membrane (ethylene, propylene, and non-conjugated diene copolymer), a polyvinyl chloride (PVC) waterproof membrane, a thermoplastic polyolefin (TPO) waterproof membrane, a HDPE polymer waterproof membrane, and a polyethylene polypropylene composite waterproof membrane.

[0053] In the present invention, the photocurable pressure-sensitive adhesive can be cross-linked in air or nitrogen under ultraviolet light of 200 to 500 nm, preferably under ultraviolet light of 350 to 400 nm.

[0054] In the present invention, the ultraviolet radiation source comprises one or more of a carbon arc, a mercury vapor arc, a fluorescent lamp with a special ultraviolet luminescent phosphor, an electronic flash lamp, a laser of a specific wavelength and an ultraviolet light emitting diode.

[0055] The technical solutions provided by the present invention are described in detail below in conjunction with the embodiments, but they should not be construed as limiting the protection scope of the present invention.

[0056] Example 1

[0057] Preparation of light-curing pressure-sensitive adhesive:

[0058] 1) 90 parts of allyl diglycol dicarbonate, 10 parts of dimethyl diallyl ammonium chloride, 40 parts of 3,4-epoxycyclohexylmethyl and 5 parts of hydroxyethyl acrylamide were mixed in 150 parts of ethylene glycol butyl ether under heating conditions of 65° C. to obtain a mixture;

[0059] 2) The mixture obtained in step 1) was mixed with 10 parts of 1-hydroxycyclohexyl phenyl ketone, and nitrogen was continuously introduced into the mixture. The reaction container was continuously irradiated with ultraviolet light of wavelength 350 nm for 30 seconds with an irradiation dose of 80 mW·cm -2 , to obtain a copolymer;

[0060] 3) The copolymer, 10 parts of diphenyl-(4-phenylthio)phenylsulfonium hexafluorophosphate and 2 parts of benzoyl peroxide were mixed under heating conditions at 130° C. to devolatilize the solvent, and finally a light-curable pressure-sensitive adhesive with a solid content of 99.9% was obtained.

[0061] Gluing and UV curing of waterproof membrane: The pressure-sensitive adhesive is evenly coated on the 600-micron thick polypropylene waterproof membrane by hot melt coating, and the coating amount is controlled at 300 microns. Then, UV curing is performed in a desktop UV curing machine (medium pressure mercury column, H lamp, 120 watts / cm2), and the UV curing dose is 250mJ / cm2 2 .

[0062] Example 2

[0063] Preparation of light-curing pressure-sensitive adhesive:

[0064] 1) 80 parts of allyl diglycol dicarbonate, 20 parts of diallylamine hydrochloride, 30 parts of 3,4-epoxycyclohexylcarboxylate and 4 parts of hydroxyethyl acrylamide were mixed in 200 parts of ethylene glycol dimethyl ether under heating conditions at 70° C. to obtain a mixture;

[0065] 2) The mixture obtained in step 1) was mixed with 8 parts of 2,2-dimethoxy-1,2-diphenylethyl-1-one, and nitrogen was continuously introduced into the mixture. The reaction container was continuously irradiated with ultraviolet light of wavelength 350 nm for 25 seconds with an irradiation dose of 85 mW·cm -2 , to obtain a copolymer;

[0066] 3) The copolymer, 8 parts of diphenyl-(4-phenylthio)phenylsulfonium hexafluorophosphate and 3 parts of benzoyl peroxide were mixed under heating conditions at 135° C. to devolatilize the solvent, and finally a light-curable pressure-sensitive adhesive with a solid content of 99.5% was obtained.

[0067] Gluing and UV curing of waterproof membrane: The pressure-sensitive adhesive is evenly coated on the 600-micron-thick polypropylene waterproof membrane by hot-melt coating, and the coating amount is controlled at 250 microns. Then, UV curing is performed in a desktop UV curing machine (medium-pressure mercury column, H lamp, 120 watts / cm2), and the UV curing dose is 250mJ / cm2. 2 .

[0068] Example 3

[0069] Preparation of light-curing pressure-sensitive adhesive:

[0070] 1) 85 parts of allyl diglycol dicarbonate, 15 parts of dimethyl diallyl ammonium chloride, 35 parts of 3,4-epoxycyclohexylmethyl and 3 parts of hydroxyethyl acrylamide were mixed in 170 parts of ether under heating conditions at 75° C. to obtain a mixture;

[0071] 2) The mixture obtained in step 1) was mixed with 8.5 parts of bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, and nitrogen was continuously introduced into the mixture. The reaction container was continuously irradiated with ultraviolet light of wavelength 350 nm for 30 seconds with an irradiation dose of 90 mW·cm -2 , to obtain a copolymer;

[0072] 3) The copolymer, 10 parts of 4-isobutylphenyl-4'-methylphenyliodine hexafluorophosphate and 2 parts of benzoyl peroxide were mixed under heating conditions at 130° C. to devolatilize the solvent, and finally a light-curable pressure-sensitive adhesive with a solid content of 99.8% was obtained.

[0073] Gluing and UV curing of waterproof membrane: The pressure-sensitive adhesive was evenly coated on the 600-micron-thick polypropylene waterproof membrane by hot-melt coating, and the coating amount was controlled at 250 microns. Then, UV curing was performed in a desktop UV curing machine (medium-pressure mercury column, H lamp, 120 watts / cm2), and the UV curing dose was 200mJ / cm2. 2 .

[0074] Example 4

[0075] Preparation of light-curing pressure-sensitive adhesive:

[0076] 1) 35 parts of allyl diglycol dicarbonate, 20 parts of oxetane, 50 parts of 3,4-epoxycyclohexylmethyl and 3 parts of hydroxyethyl acrylamide were mixed in 170 parts of diisoamyl ether under heating conditions at 90° C. to obtain a mixture;

[0077] 2) The mixture obtained in step 1) was mixed with 9 parts of 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone, and nitrogen was continuously introduced into the mixture. The reaction container was continuously irradiated with ultraviolet light of wavelength 350 nm for 30 seconds with an irradiation dose of 85 mW·cm -2 , to obtain a copolymer;

[0078] 3) The copolymer, 10 parts of diphenyl-(4-phenylthio)phenylsulfonium hexafluorophosphate and 2 parts of benzoyl peroxide were mixed under heating conditions at 130° C. to devolatilize the solvent, and finally a light-curable pressure-sensitive adhesive with a solid content of 99.7% was obtained.

[0079] Gluing and UV curing of waterproof membrane: The pressure-sensitive adhesive was evenly coated on the 600-micron-thick polypropylene waterproof membrane by hot-melt coating, and the coating amount was controlled at 250 microns. Then, UV curing was performed in a desktop UV curing machine (medium-pressure mercury column, H lamp, 120 watts / cm2), and the UV curing dose was 200mJ / cm2. 2 .

[0080] Example 5

[0081] Preparation of light-curing pressure-sensitive adhesive:

[0082] 1) 55 parts of allyl diglycol dicarbonate, 20 parts of methacryloyloxyethyl trimethyl ammonium chloride, 45 parts of 3,4-epoxycyclohexylmethyl and 5 parts of hydroxyethyl acrylamide were mixed in 200 parts of ethylene glycol dimethyl ether under heating conditions of 85° C. to obtain a mixture;

[0083] 2) The mixture obtained in step 1) was mixed with 10 parts of 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone, and nitrogen was continuously introduced into the mixture. The reaction container was continuously irradiated with ultraviolet light of a wavelength of 400 nm for 29 seconds with an irradiation dose of 82 mW·cm -2 , to obtain a copolymer;

[0084] 3) The copolymer, 10 parts of diphenyl-(4-phenylthio)phenylsulfonium hexafluorophosphate and 2 parts of benzoyl peroxide were mixed under heating conditions at 135° C. to devolatilize the solvent, and finally a light-curable pressure-sensitive adhesive with a solid content of 99.6% was obtained.

[0085] Gluing and UV curing of waterproof membrane: The pressure-sensitive adhesive was evenly coated on the 600-micron-thick polypropylene waterproof membrane by hot-melt coating, and the coating amount was controlled at 250 microns. Then, UV curing was performed in a desktop UV curing machine (medium-pressure mercury column, H lamp, 120 watts / cm2), and the UV curing dose was 200mJ / cm2. 2 .

[0086] Example 6

[0087] Preparation of light-curing pressure-sensitive adhesive:

[0088] 1) 80 parts of allyl diglycol dicarbonate, 15 parts of diallylamine, 35 parts of 3,4-epoxycyclohexylcarboxylate and 3 parts of hydroxyethyl acrylamide were mixed in 200 parts of ethylene glycol dimethyl ether under heating conditions at 70° C. to obtain a mixture;

[0089] 2) The mixture obtained in step 1) was mixed with 9 parts of 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propane-1-one, and nitrogen was continuously introduced into the mixture. The reaction container was continuously irradiated with ultraviolet light of wavelength 340 nm for 30 seconds with an irradiation dose of 80 mW·cm -2 , to obtain a copolymer;

[0090] 3) The copolymer, 9 parts of diphenyl-(4-phenylthio)phenylsulfonium hexafluorophosphate and 2 parts of benzoyl peroxide were mixed under heating conditions at 135° C. to devolatilize the solvent, and finally a light-curable pressure-sensitive adhesive with a solid content of 99.6% was obtained.

[0091] Gluing and UV curing of waterproof membrane: The pressure-sensitive adhesive was evenly coated on the 600-micron-thick polypropylene waterproof membrane by hot-melt coating, and the coating amount was controlled at 250 microns. Then, UV curing was performed in a desktop UV curing machine (medium-pressure mercury column, H lamp, 120 watts / cm2), and the UV curing dose was 200mJ / cm2. 2 .

[0092] Example 7

[0093] Preparation of light-curing pressure-sensitive adhesive:

[0094] 1) 68 parts of allyl diglycol dicarbonate, 20 parts of dimethyl diallyl ammonium chloride, 50 parts of 3,4-epoxycyclohexylcarboxylate and 5 parts of hydroxyethyl acrylamide were mixed in 200 parts of ethylene glycol dimethyl ether under heating conditions at 75° C. to obtain a mixture;

[0095] 2) The mixture obtained in step 1) was mixed with 9 parts of 1-hydroxycyclohexyl phenyl ketone, and nitrogen was continuously introduced into the mixture. The reaction container was continuously irradiated with ultraviolet light of wavelength 380 nm for 25 seconds with an irradiation dose of 80 mW·cm -2 , to obtain a copolymer;

[0096] 3) The copolymer, 9 parts of diphenyl-(4-phenylthio)phenylsulfonium hexafluorophosphate and 2 parts of benzoyl peroxide were mixed under heating conditions at 135° C. to devolatilize the solvent, and finally a light-curable pressure-sensitive adhesive with a solid content of 99.6% was obtained.

[0097] Gluing and UV curing of waterproof membrane: The pressure-sensitive adhesive is evenly coated on the 600-micron thick polypropylene waterproof membrane by hot melt coating, and the coating amount is controlled at 300 microns. Then, UV curing is performed in a desktop UV curing machine (medium pressure mercury column, H lamp, 120 watts / cm2), and the UV curing dose is 200mJ / cm2 2 .

[0098] Comparative Example 1

[0099] The existing product BASFAC250 was evenly coated on a 600 micron thick polypropylene waterproofing membrane by hot melt coating, and the coating amount was controlled at 250 microns. Then, UV curing was performed in a desktop UV curing machine (medium pressure mercury column, H lamp, 120 watts / cm2), and the UV curing dose was 250mJ / cm2. 2 .

[0100] Comparative Example 2

[0101] The existing product BASFAC260 was evenly coated on a 600 micron thick polypropylene waterproofing membrane by hot melt coating, and the coating amount was controlled at 250 microns. Then, UV curing was performed in a desktop UV curing machine (medium pressure mercury column, H lamp, 120 watts / cm2), and the UV curing dose was 250mJ / cm2. 2 .

[0102] Comparative Example 3

[0103] The pressure-sensitive adhesive was prepared by using the adhesive composition and polymerization method of Example 1 of CN201810959374.4. The pressure-sensitive adhesive was evenly coated on a 600-micron thick polypropylene waterproofing membrane by hot melt coating, and the coating amount was controlled at 250 microns. Then, UV curing was performed in a desktop ultraviolet curing machine (medium pressure mercury column, H lamp, 120 watts / cm), and the UV curing dose was 250mJ / cm 2 .

[0104] The pressure-sensitive adhesive properties of the embodiments and comparative examples were tested according to the following test methods:

[0105] The polymer coil samples of Examples 1 to 7 and Comparative Examples 1 to 3 were cut into 25 mm wide strips, then attached to a standard test steel plate, and the surface of the coil was reciprocated twice with a 2 kg standard roller. After attaching to a 23°C steel plate for 24 hours and to a 70°C steel plate for 24 hours, the 180 degree peeling force and the 23°C and 70°C holding forces were measured. The test results are shown in Tables 1 and 2.

[0106] Table 1 Performance test results of cationic curing pressure sensitive adhesives of Examples 1 to 7

[0107]

[0108] Table 2 Comparative Examples 1 to 3 Pressure Sensitive Adhesive Performance Test Results

[0109]

[0110] It can be seen from the above embodiments that the present invention provides a photocurable pressure-sensitive adhesive and its preparation method and application. The waterproof roll material prepared by the photocurable pressure-sensitive adhesive of the present invention not only has high adhesion, but also has excellent holding power. The heat resistance performance test of the photocurable pressure-sensitive adhesive obtained by the present invention shows that the heat resistance of the photocurable pressure-sensitive adhesive of the present invention is excellent, and the service life of the pressure-sensitive adhesive in the waterproof roll material can be extended. The present invention overcomes the disadvantage that the curable thickness of the free radical photocurable pressure-sensitive adhesive is <200 microns, and better meets the requirement of the polymer roll material adhesive layer thickness>250 microns stipulated in GB / T 23457 "Pre-laid / wet-laid waterproof roll materials" in my country.

[0111] The above is only a preferred embodiment of the present invention. It should be pointed out that for ordinary technicians in this technical field, several improvements and modifications can be made without departing from the principle of the present invention. These improvements and modifications should also be regarded as the scope of protection of the present invention.

Claims

1. A light-curing pressure-sensitive adhesive, characterized in that: Prepared from the following raw materials in parts by weight:

2. The light-curable pressure-sensitive adhesive according to claim 1, characterized in that: The cationic functional monomer comprises one or more of dimethyldiallylammonium chloride, diallylamine hydrochloride, methacryloyloxyethyltrimethylammonium chloride, diallylamine and oxetane.

3. The light-curable pressure-sensitive adhesive according to claim 1 or 2, characterized in that: The cationic polymerizable resin comprises 3,4-epoxycyclohexylmethyl and / or 3,4-epoxycyclohexylcarboxylate.

4. The light-curable pressure-sensitive adhesive according to claim 3, characterized in that: The photoinitiator comprises a free radical polymerization initiator, a cationic polymerization initiator and benzoyl peroxide, and the mass ratio of the free radical polymerization initiator, the cationic polymerization initiator and the benzoyl peroxide is 1-3:1-3:0.2-05.

5. The light-curable pressure-sensitive adhesive according to claim 4, characterized in that: The free radical polymerization initiator comprises one or more of 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-1,2-diphenylethyl-1-ketone, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propane-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinylphenyl)butanone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinylpropan-1-one and 2-hydroxy-2-methyl-1-phenylpropan-1-one.

6. The light-curable pressure-sensitive adhesive according to claim 4 or 5, characterized in that: The cationic polymerization initiator comprises diphenyl-(4-phenylthio)phenylsulfonium hexafluorophosphate and / or 4-isobutylphenyl-4′-methylphenyliodonium hexafluorophosphate.

7. The light-curable pressure-sensitive adhesive according to claim 6, characterized in that: The organic solvent comprises one or more of ethylene glycol dimethyl ether, ethylene glycol butyl ether, diethyl ether and diisoamyl ether.

8. The method for preparing the light-curable pressure-sensitive adhesive according to any one of claims 1 to 7, characterized in that: The following steps are involved: 1) mixing allyl diglycol dicarbonate, a cationic functional monomer, a cationic polymerizable resin and hydroxyethyl acrylamide in an organic solvent to obtain a mixture; 2) mixing the mixture with a free radical polymerization initiator, introducing a protective gas into the mixture, and obtaining a copolymer under continuous ultraviolet irradiation; 3) Mixing the copolymer, the cationic polymerization initiator and benzoyl peroxide under heating conditions to finally obtain a light-curable pressure-sensitive adhesive.

9. The preparation method according to claim 8, characterized in that: In the step 1), the mixing is carried out under heating conditions, and the heating temperature is 60 to 90° C.; In step 2), the ultraviolet irradiation conditions are: irradiation dose 70 to 90 mW·cm -2 , irradiate for 20 to 40 seconds, the peak wavelength of ultraviolet light is 340 to 400 nm; In the step 3), the heating temperature is 120-150°C.

10. Use of the photocurable pressure-sensitive adhesive according to any one of claims 1 to 7 in waterproof membranes.

Images