CN115322740A - Ultraviolet light curing pressure-sensitive adhesive and preparation method thereof - Google Patents
Ultraviolet light curing pressure-sensitive adhesive and preparation method thereof Download PDFInfo
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- CN115322740A CN115322740A CN202211033155.6A CN202211033155A CN115322740A CN 115322740 A CN115322740 A CN 115322740A CN 202211033155 A CN202211033155 A CN 202211033155A CN 115322740 A CN115322740 A CN 115322740A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on 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; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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- 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
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Abstract
The application discloses an ultraviolet curing pressure-sensitive adhesive and a preparation method thereof, wherein the ultraviolet curing pressure-sensitive adhesive comprises the following components in parts by weight: 50-80 parts of acrylate monomer, 40-50 parts of modified polysiloxane, 20-30 parts of epoxy acrylate resin and 1-10 parts of photoinitiator. The application has the advantages of reducing the shrinkage rate of the curing film, improving the bonding force of the adhesive and simultaneously ensuring that the ultraviolet curing pressure-sensitive adhesive has the effects of water resistance, weather resistance, environmental protection and the like.
Description
Technical Field
The application relates to the technical field of adhesives, in particular to an ultraviolet curing pressure-sensitive adhesive and a preparation method thereof.
Background
The ultraviolet curing technology is a technology for achieving rapid curing by initiating a monomer to perform chemical reactions such as polymerization, grafting, crosslinking and the like by using a photoinitiator under the irradiation of ultraviolet light. The ultraviolet curing pressure-sensitive adhesive prepared by the ultraviolet curing technology is a novel energy-saving environment-friendly pressure-sensitive adhesive, generates the required pressure-sensitive adhesion by grafting and crosslinking curing under the irradiation of ultraviolet light, and has the advantages of high curing speed, quick curing at room temperature, no need of heating, no organic solvent, less pollution, adjustability of product performance and the like.
The ultraviolet curing pressure-sensitive adhesive is mainly based on a free radical photocuring mode, has high reaction speed and mature curing process, but the free radical type curing system has oxygen inhibition, thick layers and colored systems are difficult to cure, and the volume shrinkage rate after curing is large.
Disclosure of Invention
In order to reduce the shrinkage rate of a curing film, improve the bonding force of the adhesive and ensure that the ultraviolet curing pressure-sensitive adhesive has the performances of water resistance, weather resistance, environmental protection and the like, the application provides the ultraviolet curing pressure-sensitive adhesive and the preparation method thereof.
In a first aspect, the application provides an ultraviolet light curing pressure sensitive adhesive, which adopts the following technical scheme:
the ultraviolet curing pressure-sensitive adhesive is characterized by comprising the following components in parts by weight:
50-80 parts of acrylate monomer;
40-50 parts of modified polysiloxane;
20-30 parts of epoxy acrylate resin;
1-10 parts of a photoinitiator;
the modified polysiloxane has a structural formula described by formula (1):
in the formula (1), a is more than or equal to 0 and less than or equal to 50,1 and less than or equal to b 2,5 and less than or equal to c and less than or equal to 20,1 and less than or equal to d and less than or equal to 3.
Preferably, the acrylate monomer includes one or more of a monofunctional acrylate monomer, a difunctional acrylate monomer, and a trifunctional acrylate monomer.
Preferably, the photoinitiator is selected from one of benzoin dimethyl ether, benzoin ethyl ether, α' -dimethoxy- α -phenylacetophenone, α -diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, 1-hydroxy-cyclohexylbenzophenone, 2-hydroxy-2-methyl-p-hydroxyethyl ether phenyl propanone-1, benzophenone and ethyl 4-dimethylaminobenzoate.
Preferably, the paint also comprises 1-5 parts of an auxiliary agent, wherein the auxiliary agent is selected from one of a stabilizing agent, a leveling agent, a defoaming agent and a plasticizer.
Preferably, the modified polysiloxane is prepared by the following method:
adding hydrogen-containing polysiloxane, a solvent and a hydrosilylation catalyst into a reaction kettle, stirring and heating to 90-130 ℃, slowly dripping vinyl silane coupling agent under the protection of nitrogen in the reaction process, continuously and slowly dripping allyl methacrylate after the dripping of the vinyl silane coupling agent is finished, keeping the temperature at 90-130 ℃, reacting and removing the solvent to obtain the modified polysiloxane.
Preferably, the solvent is selected from one of toluene or xylene; the hydrosilylation catalyst is selected from one of a Sperier catalyst or a Karstedt catalyst.
Preferably, the hydrogen content of the hydrogenpolysiloxane is 0.9-5mmol/g, and the viscosity of the hydrogenpolysiloxane at 25 ℃ is 70-120 cp.
In a second aspect, the present application provides a method for preparing an ultraviolet light curing pressure-sensitive adhesive, which comprises the following process flows:
and sequentially adding an acrylate monomer, modified polysiloxane, epoxy acrylate resin and a photoinitiator into a reaction kettle provided with a stirrer and a nitrogen protection device, uniformly stirring, and curing for 25-55s under the condition that the wavelength of ultraviolet light is 180-450nm to obtain the ultraviolet light curing pressure-sensitive adhesive.
In summary, the present application includes at least one of the following beneficial technical effects:
(1) The invention modifies polysiloxane, selects hydrogen-containing polysiloxane, has longer Si-O-Si bond, is very soft, can delay the shrinkage rate of a curing film, has strong antioxidation and polymerization inhibition effects and high hydrogen supply efficiency, adds allyl methacrylate to prepare polysiloxane macromolecules with a certain chain length and carbon-carbon double bonds according to hydrosilylation reaction because of higher activity of the Si-H bond, and introduces-Si (OR) on the polysiloxane macromolecules by adding the vinyl silane coupling agent 3 Group(s) such thatThe bonding interface forms a chemical bond with higher strength, the adhesive force between the adhesive and the bonding interface is improved, and the bonding strength is greatly improved. And by controlling the dosage of the vinyl silane coupling agent and the allyl methacrylate, a part of Si-H bonds which do not participate in the hydrosilylation reaction are left in the hydrogen-containing polysiloxane, and the Si-H bonds have stronger reducibility, so that the oxygen inhibition in the curing process can be effectively reduced.
(2) According to the invention, the acrylate monomer, the modified polysiloxane and the epoxy acrylate resin are blended and crosslinked, and the epoxy acrylate resin can reduce the volume shrinkage rate in the curing process and has good heat resistance, chemical resistance and high bonding force, so that the environment-friendly ultraviolet curing pressure-sensitive adhesive with high waterproofness, high bonding force and high weather resistance is prepared.
Detailed Description
The present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto.
Example 1:
adding 50 parts of methyl hydrogen-containing silicone oil with the hydrogen content of 3mmol/g and the viscosity of 100cp at 25 ℃, 60 parts of toluene and 0.5 part of Karstedt catalyst into a reaction kettle provided with a mechanical stirring device, a thermometer, a reflux condenser tube, a dropping funnel and a nitrogen protection device, heating to 120 ℃ while stirring, slowly dropping 20 parts of vinyl triethoxysilane into the solution for 20min under the protection of nitrogen, continuously dropping 3 parts of allyl methacrylate into the solution for 5min after dropping, stirring for 1 hour at 120 ℃, removing the toluene in vacuum after the reaction is finished to obtain modified polysiloxane, then taking another reaction kettle provided with a mechanical stirring device and a nitrogen protection device, sequentially adding the modified polysiloxane, 35 parts of pentaerythritol triacrylate, 30 parts of iso-acrylate, 25 parts of epoxy acrylate resin, 5 parts of benzoin bismethyl ether and 2 parts of defoaming agent, uniformly stirring and mixing, and uniformly coating the prepared adhesive on a polyester film under the condition that the wavelength of ultraviolet light is 400nm and is cured for 40s.
Example 2:
this example is different from example 1 in that allyl methacrylate was used in an amount of 2 parts, and the rest was the same as example 1.
Example 3:
this example is different from example 1 in that allyl methacrylate is used in an amount of 1 part, and the rest is the same as example 1.
Example 4:
this example is different from example 1 in that vinyltriethoxysilane is used in an amount of 18 parts, and the rest is the same as example 1.
Example 5:
this example is different from example 1 in that vinyltriethoxysilane is used in an amount of 16 parts, and the rest is the same as example 1.
Example 6:
this example is different from example 1 in that the epoxy acrylate resin is used in an amount of 20 parts, and the rest is the same as example 1.
Example 7:
this example is different from example 1 in that the amount of the epoxy acrylate resin used is 15 parts, and the rest is the same as example 1.
Comparative example 1:
adding 35 parts of pentaerythritol triacrylate, 30 parts of isoborneol acrylate, 25 parts of epoxy acrylate resin, 5 parts of benzoin dimethyl ether and 2 parts of defoaming agent into a reaction kettle provided with a mechanical stirring and nitrogen protection device in sequence, uniformly stirring and mixing, uniformly coating the prepared adhesive on a polyester film, and curing for 40s under the wavelength of ultraviolet light of 400 nm.
Comparative example 2:
adding 35 parts of pentaerythritol triacrylate, 30 parts of isoborneol acrylate, 50 parts of polysiloxane, 5 parts of benzoin dimethyl ether and 2 parts of defoaming agent into a reaction kettle with a mechanical stirring and nitrogen protection device in sequence, uniformly stirring and mixing, uniformly coating the prepared adhesive on a polyester film, and curing for 40s under the condition that the wavelength of ultraviolet light is 400 nm.
Comparative example 3:
adding 35 parts of pentaerythritol triacrylate, 30 parts of isoborneol acrylate, 50 parts of polysiloxane, 25 parts of epoxy acrylate resin, 5 parts of benzoin dimethyl ether and 2 parts of defoaming agent into a reaction kettle provided with a mechanical stirring and nitrogen protection device in sequence, uniformly stirring and mixing, uniformly coating the prepared adhesive on a polyester film, and curing for 40s under the wavelength of ultraviolet light of 400 nm.
The ultraviolet light curing pressure sensitive adhesive prepared in the above examples and comparative examples is tested for application effect, and the specific test method is as follows:
1. permanent tack test of UV-cured pressure sensitive adhesives
According to the method for testing the permanent adhesion of the pressure-sensitive adhesive tape in GB/T4851-1998, the adhesive and the polyester film are completely contacted during the test, the test is carried out after the adhesive and the polyester film are placed for 20min, a constant weight is hung under a test strip, and the test result of the permanent adhesion is represented by the total time (min) for the weight to fall measured after the test strip is placed for 20 min.
2. 180-degree peel strength test of ultraviolet curing pressure-sensitive adhesive
According to the test method of GB/T2792-1998 180 DEG peel strength of the adhesive, the adhesive and the polyester film are completely contacted, the adhesive is placed on a tensile tester for testing after being placed for 20min, and the test result of 180 DEG peel adhesion is represented by the average value of the peel force (N/25 mm) of 3 sample strips measured at 20min rest time.
The test results obtained are described in table 1:
| viscosity (min) | Peel force (N/25 mm) | |
| Example 1 | 2170 | 23 |
| Example 2 | 2358 | 24 |
| Example 3 | 2018 | 22 |
| Example 4 | 2089 | 22 |
| Example 5 | 1978 | 19 |
| Example 6 | 2008 | 17 |
| Example 7 | 1867 | 15 |
| Comparative example 1 | 1470 | 14 |
| Comparative example 2 | 1568 | 12 |
| Comparative example 3 | 1701 | 13 |
TABLE 1
As can be obtained by analyzing the results of the above-mentioned experiments,
1. the comparison of the test results of example 1, example 2 and example 3 shows that the modified polysiloxane with a certain chain length and carbon-carbon double bonds is prepared by adding a certain amount of allyl methacrylate, and the modified polysiloxane is cross-linked and cured with isoborneol acrylate and pentaerythritol triacrylate, so that the flexibility of the adhesive can be improved, the shrinkage rate of a cured film is reduced, and the bonding force is enhanced.
2. As can be seen from the comparison of the test results of example 1, example 4 and example 5, by adding vinyltriethoxysilane, use is made of-Si (OC) 2 H 5 ) 3 The group enables the bonding interface to form a chemical bond with higher strength, improves the adhesive force between the adhesive and the bonding interface, and has higher content of the vinyl silane coupling agent and stronger adhesive force.
3. The comparison of the test results of the embodiment 1, the embodiment 6 and the embodiment 7 shows that the volume shrinkage rate in the curing process can be reduced and the adhesive force of the adhesive can be improved by adding the epoxy acrylate resin, and the comprehensive performance of the adhesive can be improved by adopting the epoxy acrylate resin with higher content.
4. By comparing the test results of the example 1, the comparative example 2 and the comparative example 3, the comprehensive performance of the ultraviolet curing pressure-sensitive adhesive can be effectively improved by preparing the modified polysiloxane, and blending and crosslinking the modified polysiloxane with isoborneol acrylate, pentaerythritol triacrylate and epoxy acrylate resin.
The present embodiment is only for explaining the present application, and it is not limited to the present application, and those skilled in the art can make modifications of the present embodiment without inventive contribution as needed after reading the present specification, but all of them are protected by patent law within the scope of the claims of the present application.
Claims (8)
1. The ultraviolet curing pressure-sensitive adhesive is characterized by comprising the following components in parts by weight:
50-80 parts of acrylate monomer;
40-50 parts of modified polysiloxane;
20-30 parts of epoxy acrylate resin;
1-10 parts of a photoinitiator;
the modified polysiloxane has a structural formula described by formula (1):
in the formula (1), a is more than or equal to 0 and less than or equal to 50,1 and less than or equal to b 2,5 and less than or equal to c and less than or equal to 20,1 and less than or equal to d and less than or equal to 3.
2. The UV-curable pressure-sensitive adhesive according to claim 1, wherein the acrylate monomer comprises one or more of a monofunctional acrylate monomer, a difunctional acrylate monomer and a trifunctional acrylate monomer.
3. The UV-curable pressure-sensitive adhesive according to claim 1, wherein the photoinitiator is selected from the group consisting of benzoin dimethyl ether, benzoin ethyl ether, α' -dimethoxy- α -phenylacetophenone, α -diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, 1-hydroxy-cyclohexylbenzophenone, 2-hydroxy-2-methyl-p-hydroxyethyl ether phenyl propanone-1, benzophenone and ethyl 4-dimethylaminobenzoate.
4. The UV-curable pressure-sensitive adhesive according to claim 1, further comprising 1-5 parts of an auxiliary agent, wherein the auxiliary agent is selected from one of a stabilizer, a leveling agent, an antifoaming agent and a plasticizer.
5. The UV-curable pressure-sensitive adhesive according to claim 1, wherein the modified polysiloxane is prepared by the following steps:
adding hydrogen-containing polysiloxane, a solvent and a hydrosilylation catalyst into a reaction kettle, stirring and heating to 90-130 ℃, slowly dropwise adding a vinyl silane coupling agent under the protection of nitrogen in the reaction process, continuously and slowly dropwise adding allyl methacrylate after the dropwise adding of the vinyl silane coupling agent is finished, keeping the temperature at 90-130 ℃, reacting and removing the solvent to obtain the modified polysiloxane.
6. The UV-curable pressure-sensitive adhesive according to claim 5, wherein the solvent is selected from one of toluene and xylene, and the hydrosilylation catalyst is selected from one of Sperier catalyst and Karstedt catalyst.
7. The UV-curable pressure-sensitive adhesive according to claim 5, wherein the hydrogen-containing polysiloxane has a hydrogen content of 0.9 to 5mmol/g and a viscosity of 70 to 120cp at 25 ℃.
8. The method for preparing the ultraviolet curing pressure-sensitive adhesive as set forth in any one of claims 1 to 7, characterized in that the method comprises the following process flows:
and sequentially adding an acrylate monomer, modified polysiloxane, epoxy acrylate resin and a photoinitiator into a reaction kettle provided with a stirrer and a nitrogen protection device, uniformly stirring, and curing for 25-55s under the condition that the wavelength of ultraviolet light is 180-450nm to obtain the ultraviolet light curing pressure-sensitive adhesive.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115725262A (en) * | 2022-11-16 | 2023-03-03 | 广州回天新材料有限公司 | Adhesive and preparation method and application thereof |
| CN115785874A (en) * | 2022-12-20 | 2023-03-14 | 清远职业技术学院 | Light-cured epoxy acrylic resin conductive adhesive and preparation method thereof |
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| CN115785874A (en) * | 2022-12-20 | 2023-03-14 | 清远职业技术学院 | Light-cured epoxy acrylic resin conductive adhesive and preparation method thereof |
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