CN114989731A - Polyacrylate/organic silicon hybrid pressure-sensitive adhesive - Google Patents
Polyacrylate/organic silicon hybrid pressure-sensitive adhesive Download PDFInfo
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- CN114989731A CN114989731A CN202210559127.1A CN202210559127A CN114989731A CN 114989731 A CN114989731 A CN 114989731A CN 202210559127 A CN202210559127 A CN 202210559127A CN 114989731 A CN114989731 A CN 114989731A
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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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
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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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/064—Copolymers with monomers not covered by C09J133/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation
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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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/04—Polymer mixtures characterised by other features containing interpenetrating networks
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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
- C09J2433/00—Presence of (meth)acrylic polymer
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention provides a polyacrylate/organosilicon hybrid pressure-sensitive adhesive, which comprises a component (A), (methyl) acrylate prepolymer, a component (B), polyfunctional organic siloxane capable of free radical polymerization, a component (C), a free radical photoinitiator, a component (D) and an antioxidant. According to the polyacrylate/organosilicon hybrid pressure-sensitive adhesive, the introduced organosilicon components form an Interpenetrating Polymer Network (IPN) in the whole molecular network, and the high-temperature resistance of the organosilicon is fully utilized, so that the temperature resistance grade of the whole acrylate/organosilicon hybrid pressure-sensitive adhesive system can be remarkably improved, and the application range is expanded.
Description
Technical Field
The invention relates to the field of high polymer materials, in particular to a polyacrylate/organic silicon hybrid pressure-sensitive adhesive.
Background
The statements in this section merely provide background information related to the present disclosure and may not constitute prior art.
Polyacrylate pressure-sensitive adhesives have many unique properties compared to pressure-sensitive adhesives of other materials (e.g., rubber-type, silicone, polyurethane, etc.), such as: excellent aging resistance (especially ultraviolet light aging resistance), excellent optical transparency, pressure sensitivity without adding tackifying resin, high temperature resistance, low temperature resistance and moderate price, and is widely used in transportation, electronic power and building markets. Commonly used pressure sensitive adhesives are generally prepared by random copolymerization of soft monomers such as isooctyl acrylate (IOA) or 2-ethylhexyl acrylate (2-EHA), hard monomers such as isobornyl acrylate (IBOA) and Methyl Methacrylate (MMA), and functional monomers such as Acrylic Acid (AA), methacrylic acid (MAA), and hydroxyethyl acrylate (2-HEA). Such pressure sensitive adhesives have desirable peel and shear strengths for most bonded surfaces.
However, polyacrylate pressure sensitive adhesives generally cannot withstand particularly high temperatures. The polyacrylate polymer can be slowly degraded at high temperature (such as 125 ℃) to cause the molecular weight to be reduced, thereby reducing the cohesive property of the pressure-sensitive adhesive; high temperature degradation also produces bubbles, further resulting in reduced adhesion properties.
There is a need to develop a polyacrylate pressure-sensitive adhesive capable of withstanding higher temperatures to solve the problem of easy degradation at high temperatures.
It should be noted that the above background description is only for the sake of clarity and complete description of the technical solutions of the present invention and for the understanding of those skilled in the art. Such solutions are not considered to be known to the person skilled in the art merely because they have been set forth in the background section of the invention.
Disclosure of Invention
The invention aims to solve the technical problem of providing a high-temperature-resistant polyacrylate/organic silicon hybrid pressure-sensitive adhesive to solve the problem of easy degradation at high temperature.
In order to solve the technical problems, the invention provides a polyacrylate/organic silicon hybrid pressure-sensitive adhesive, which comprises,
component (A), (meth) acrylate prepolymer,
a component (B), a radically polymerizable polyfunctional organosiloxane,
component (C), a free-radical photoinitiator, and,
component (D), an antioxidant.
Preferably, the component (A), the (meth) acrylate prepolymer, contains the following monomer components,
(a1) a (meth) acrylate monomer having an alkyl group with 1 to 12 carbon atoms,
(a2) (meth) acrylic acid monomers.
Preferably, the alkyl (meth) acrylate in component (a1) is one or more of methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate.
Preferably, the alkyl (meth) acrylate in component (a1) is a mixture of one or more of methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, and tert-butyl (meth) acrylate.
Preferably, the alkyl (meth) acrylate of component (a1) is one or more of butyl (meth) acrylate, methyl (meth) acrylate, and isooctyl (meth) acrylate.
Preferably, component (a1) is 80-99% by weight of component (A) and component (a2) is 1-20% by weight of component (A).
Preferably, (a1) represents 90-97% by weight of component (A) and component (a2) represents 3-10% by weight of component (A).
Preferably, both ends of the multifunctional organic siloxane capable of free radical polymerization of the component (B) contain acrylate double bonds capable of free radical polymerization, the structural formula is shown as a formula (II), the molecular weight is 100-5000, and R1 is alkyl; r2 is methyl or H; r3 is a methyl group or a phenyl group,
wherein R1 is alkyl; r2 is methyl or H; r3 is a methyl group or a phenyl group,
the multifunctional organic siloxane containing acrylate double bonds capable of free radical polymerization at two ends can play a role of a cross-linking agent after being copolymerized into an acrylate copolymer main chain, so that IPN is formed, and the high temperature resistance of the pressure-sensitive adhesive can be obviously enhanced.
The weight percentage of the component (B) in the acrylate/organic silicon hybrid pressure-sensitive adhesive is 1-10%. More preferably 2-8%. B) If the content of (A) is too low, the high temperature resistance cannot be achieved, and if the content of (B) is too high, the mechanical property (particularly the peeling force) of the pressure-sensitive adhesive is affected
Preferably, the free radical photoinitiator of component (C) is one or a mixture of more of 2, 2-dimethoxy-2-phenylacetophenone (BDK), 1-hydroxycyclohexyl phenyl ketone (184), 2-hydroxy-2-methyl-1-phenylpropan-1-one (1173), 2 (or 4) -Isopropylthioxanthone (ITX)2,4, 6-trimethylbenzoyl diphenylphosphine oxide (TPO), bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide (819).
Another important component of the acrylate/organosilicon hybrid pressure-sensitive adhesive is a free radical photoinitiator. Free radical photoinitiators are compounds that, when exposed to light, undergo photochemical reactions to generate free radicals. The free radicals generated by the free radical type photoinitiator may cause a free radical polymerization reaction of the system to cure. Photoinitiators of different structures have different absorption spectra and radical activities.
Preferably, the weight percentage of the free radical photoinitiator of the component (C) in the acrylate/organosilicon hybrid pressure-sensitive adhesive is 0.001-5.0%. More preferably between 0.2 and 2.2%.
The content of the free radical type photoinitiator is too low, the speed of the acrylate/organic silicon hybrid pressure-sensitive adhesive is too low during ultraviolet irradiation curing, and the coating speed is low; the content of the free radical type photoinitiator is too high, the speed of the acrylate/organic silicon hybrid pressure-sensitive adhesive is too high during ultraviolet irradiation curing, and the molecular weight of the obtained acrylate copolymer is too low, so that the mechanical property of the pressure-sensitive adhesive is influenced.
Preferably, the antioxidant of the component (D) is one or a mixture of more of an antioxidant 1010, an antioxidant 1076, an antioxidant CA, an antioxidant 164, an antioxidant 168, an antioxidant DNP, an antioxidant DLTP, an antioxidant TNP, an antioxidant TPP, an antioxidant MB and an antioxidant 264, and the weight percentage of the component (D) in the acrylate/organosilicon hybrid pressure-sensitive adhesive is 0.05-5.0%. More preferably between 0.2 and 1.8%. If the content of the antioxidant is too low, the requirement for improving the temperature resistance of the pressure-sensitive adhesive cannot be met; too high an antioxidant content not only makes it unnecessary and increases costs, but may also cause precipitation from the pressure-sensitive adhesive system and affect performance.
Antioxidants as component (D) are conventionally visible. The thermal oxidation process of the pressure-sensitive adhesive is a series of free radical chain reactions, and under the action of heat, light or oxygen, chemical bonds of pressure-sensitive adhesive molecules are broken to generate active free radicals and hydroperoxide. The hydroperoxide undergoes decomposition reactions, which also generate hydroxyl radicals and hydroxyl radicals. These radicals can initiate a series of radical chain reactions that result in fundamental changes in the structure and properties of the pressure sensitive adhesive. The antioxidant functions to scavenge the free radicals that have just been generated or to promote the decomposition of the hydroperoxide, preventing the chain reaction from proceeding. The antioxidant capable of eliminating free radicals is a compound such as aromatic amine, hindered phenol and the like and a derivative thereof, and is called as a main antioxidant; antioxidants capable of decomposing hydroperoxides are organic compounds containing phosphorus and sulfur, called secondary antioxidants.
By means of the technical scheme, the invention has the following beneficial effects:
according to the polyacrylate/organosilicon hybrid pressure-sensitive adhesive, the introduced organosilicon components form an Interpenetrating Polymer Network (IPN) in the whole molecular network, and the high-temperature resistance of the organosilicon is fully utilized, so that the temperature resistance grade of the whole acrylate/organosilicon hybrid pressure-sensitive adhesive system can be remarkably improved, and the application range is expanded.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The polyacrylate/organosilicon hybrid pressure-sensitive adhesive comprises a component (A), a (methyl) acrylate prepolymer, a component (B), polyfunctional organic siloxane capable of free radical polymerization, a component (C), a free radical photoinitiator, a component (D) and an antioxidant.
The component (A) and the (meth) acrylate prepolymer contain (a1) a (meth) acrylate monomer having an alkyl group with 1-12 carbon atoms, and (a2) a (meth) acrylic acid monomer.
The alkyl (meth) acrylate in the component (a1) is one or a mixture of methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate.
The two ends of the multifunctional organic siloxane capable of performing free radical polymerization reaction of the component (B) contain acrylate double bonds capable of performing free radical polymerization reaction, the structural formula is shown as a formula (II), the molecular weight is 100-5000, and R1 is alkyl; r2 is methyl or H; r3 is a methyl group or a phenyl group,
wherein R1 is alkyl; r2 is methyl or H; r3 is methyl or phenyl.
The radical photoinitiator of component (C) is one or a mixture of more of 2, 2-dimethoxy-2-phenylacetophenone (BDK), 1-hydroxycyclohexyl phenyl ketone (184), 2-hydroxy-2-methyl-1-phenylpropan-1-one (1173), 2 (or 4) -Isopropylthioxanthone (ITX)2,4, 6-trimethylbenzoyl diphenyl phosphine oxide (TPO), bis (2,4, 6-trimethylbenzoyl) -phenyl phosphine oxide (819).
The antioxidant of the component (D) is one or a mixture of more of an antioxidant 1010, an antioxidant 1076, an antioxidant CA, an antioxidant 164, an antioxidant 168, an antioxidant DNP, an antioxidant DLTP, an antioxidant TNP, an antioxidant TPP, an antioxidant MB and an antioxidant 264.
The viscosity of the acrylate/organosilicon hybrid pressure-sensitive adhesive composition before being cured by ultraviolet radiation is 500-50000 cPs, and more preferably 1500-16000 cPs. The coating of the acrylate/organosilicon hybrid pressure-sensitive adhesive is not favorable when the viscosity is too high or too low.
The acrylate/organosilicon hybrid pressure-sensitive adhesive can be coated on two layers of transparent PET release films with certain thickness in a liquid state by a coating mode, and then an adhesive film with the required thickness is formed by an ultraviolet radiation curing process.
The light intensity setting and the residence time of the ultraviolet light oven can be referred to the following parameters:
Zone1：2.2mw/cm 2 the residence time is 50 seconds;
Zone2：9.1mw/cm 2 the retention time is 60 seconds;
Zone3：18mw/cm 2 the residence time was 9 seconds.
Watch 1
The (meth) acrylate prepolymer (A) was prepared as follows,
adding 2-EHA, AA monomers and a free radical photoinitiator into a transparent glass bottle filled with nitrogen according to the composition of the table II, irradiating for a certain time by using a UV LED (385nm) lamp under stirring until the viscosity reaches 3000-6000 cPs, stopping UV light irradiation, and cooling to obtain a transparent viscous liquid, namely the (methyl) acrylate prepolymer (A).
Watch 2
Examples 1 to 35
Uniformly mixing (methyl) acrylate prepolymer (A), polyfunctional organic siloxane (B) capable of undergoing free radical polymerization reaction, free radical photoinitiator (C) and antioxidant (D) according to the composition of the third table, coating according to the coating method of the acrylate/organic silicon hybrid pressure-sensitive adhesive composition to obtain a 125-micron adhesive film, attaching a 50-micron-thick PET film to one surface of the adhesive film to obtain a single-sided adhesive tape, and evaluating 180-degree stripping force and high-temperature static shear strength of the adhesive tape; the high temperature resistance evaluation directly uses a 125 micron pure glue film.
Watch III
| A1 | A2 | A3 | X-22-164 | X-22-164A | X-22-164E | Irganox 1010 | Irgafos 168 | Irgacure 651 | |
| Sample 1 | 100 | 0.2 | |||||||
| Sample 2 | 100 | 2 | 0.2 | ||||||
| Sample 3 | 100 | 5 | 0.2 | ||||||
| Sample 4 | 100 | 10 | 0.2 | ||||||
| Sample No. 5 | 100 | 2 | 1 | 0.5 | 0.2 | ||||
| Sample No. 6 | 100 | 5 | 1 | 0.5 | 0.2 | ||||
| Sample 7 | 100 | 10 | 1 | 0.5 | 0.2 | ||||
| Sample 8 | 100 | 0.2 | |||||||
| Sample 9 | 100 | 2 | 0.2 | ||||||
| Sample 10 | 100 | 5 | 0.2 | ||||||
| Sample 11 | 100 | 10 | 0.2 | ||||||
| Sample 12 | 100 | 2 | 1 | 0.5 | 0.2 | ||||
| Sample 13 | 100 | 5 | 1 | 0.5 | 0.2 | ||||
| Sample 14 | 100 | 10 | 1 | 0.5 | 0.2 | ||||
| Sample 15 | 100 | 0.2 | |||||||
| Sample 16 | 100 | 2 | 0.2 | ||||||
| Sample 17 | 100 | 5 | 0.2 | ||||||
| Sample 18 | 100 | 10 | 0.2 | ||||||
| Sample 19 | 100 | 2 | 1 | 0.5 | 0.2 | ||||
| Sample 20 | 100 | 5 | 1 | 0.5 | 0.2 | ||||
| Sample 21 | 100 | 10 | 1 | 0.5 | 0.2 |
Method for evaluating adhesive tape
Peel strength at 1.180 degrees
The 180-degree peel strength test method is carried out according to the method of national standard (GB 2792-81).
The tape was cut into 1 inch (2.54cm) wide strips of greater than 200mm in length, gently attached to a standard stainless steel test plate (in accordance with GB/T3280 and 1992) and rolled on the sample at a speed of about 300mm/min using a 2.04kg weight hard rubber roller. Note that in the rolling, the force generated by the mass of the rolls can be applied to the sample and the rolling is repeated three times. The test pieces were placed in an environment of constant temperature 23 ℃. + -. 2 ℃ and constant humidity 50% RH. + -. 5% RH for 72 hours, and the peel force was measured three times per sample using a standard tensile machine (meeting the requirements of JB 706-77 for an identification tester) at a rate of 12 inches/minute (303mm/min), and the mean value was taken in N/mm.
2. High temperature static shear Strength (holding viscosity)
Method for testing high-temperature static shear strength (permanent tack) the test was carried out according to the method of national Standard (GB/T4851).
The tape was cut into 1 inch (2.54cm) wide strips approximately 100mm long. The sample strips were adhered parallel to the longitudinal direction of the plate in the middle of a test plate (in conformity with the provisions of GB/T3280-1992) of standard stainless steel closely adjacent thereto, ensuring an adhesion area of 1 square inch. The sample was rolled at a speed of about 300mm/min using a 2.04kg weight hard rubber roller. Note that in the rolling, the sample was rolled three times in a reciprocating manner with only the force generated by the mass of the rolls. The test plate was placed in a constant temperature 23 ℃. + -. 2 ℃ constant humidity 50% RH. + -. 5% RH controlled environment for 72 hours, then the test plate was vertically fixed on the test frame, and the load plate and the 1kg weight were gently connected by a pin. The entire test stand was placed in a test chamber adjusted to 70 ℃. The time at which the test specimen fell off the test plate was recorded and each sample tested three times, and the average was taken in minutes.
3. Evaluation of high Temperature resistance-measurement of Oxidation Start Temperature-OOT
The evaluation of the high Temperature resistance of the pressure-sensitive adhesive is judged by the Method of measuring the "Oxidation initiation Temperature", and the specific sample preparation and Test Method is referred to ASTM E2009-99(Standard Test Method for Oxidation on set Test of Hydrocarbons by Differential Scanning calibration, American Society for Testing and Materials, West Conshooken, Pa.), which is briefly described as follows:
1, calibrating the heating rate to be 10 ℃/minute by using indium-tin calibration heat release of a DSC instrument;
2. the sample weighing analytical balance needs to reach 0.01mg precision;
3. open aluminum pan (no lid) for the measurement of the samples;
4. the weight of the test sample is between 3.0 and 3.5 mg;
sample OOT was tested using TA Q100 DSC. The purge air flow rate was 50 millilites/minute. The sample was heated linearly at a rate of 10 ℃/minute from 30 ℃ until the sample started to exotherm. Results are reported in (deg.C).
The test results of the tape samples according to the above evaluation method are shown in Table four.
Watch four
| 180 degree peel strength (N/mm) | 70 degree static shear Strength (min) | OOT(℃) | |
| Sample 1 | 0.62 | <1 | 187.2 |
| Sample 2 | 0.7 | 2111 | 207.5 |
| Sample 3 | 0.88 | 3678 | 218.1 |
| Sample No. 4 | 0.43 | 5588 | 228.6 |
| Sample No. 5 | 0.68 | 1890 | 225.1 |
| Sample No. 6 | 0.85 | 3276 | 245.9 |
| Sample 7 | 0.4 | 6651 | 253.4 |
| Sample 8 | 0.84 | <1 | 192.5 |
| Sample 9 | 1.23 | 8734 | 277.6 |
| Sample 10 | 1.39 | >10000 | 293.4 |
| Sample 11 | 0.56 | >10000 | 303.6 |
| Sample 12 | 1.2 | >10000 | 288.8 |
| Sample 13 | 1.41 | >10000 | 301.9 |
| Sample 14 | 0.55 | >10000 | 311.1 |
| Sample 15 | 0.65 | <1 | 201 |
| Sample 16 | 0.56 | >10000 | 295.2 |
| Sample 17 | 0.49 | >10000 | 304.4 |
| Sample 18 | 0.37 | >10000 | 312.2 |
| Sample 19 | 0.55 | >10000 | 309.9 |
| Sample 20 | 0.42 | >10000 | 320.1 |
| Sample 21 | 0.33 | >10000 | 328.8 |
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of the present invention is not limited thereto. The equivalent substitution or change made by the technical personnel in the technical field on the basis of the invention is all within the protection scope of the invention. The protection scope of the invention is subject to the claims.
Claims (10)
1. A polyacrylate/organosilicon hybrid pressure-sensitive adhesive is characterized by comprising,
component (A), (meth) acrylate prepolymer,
a component (B), a radically polymerizable polyfunctional organosiloxane,
component (C), a free-radical photoinitiator, and,
component (D), an antioxidant.
2. The polyacrylate/silicone hybrid pressure-sensitive adhesive according to claim 1, wherein the component (A), (meth) acrylate prepolymer contains the following monomer components,
(a1) a (meth) acrylate monomer having an alkyl group with 1 to 12 carbon atoms,
(a2) (meth) acrylic acid monomers.
3. The polyacrylate/silicone hybrid pressure-sensitive adhesive according to claim 2, wherein the alkyl (meth) acrylate in component (a1) is a mixture of one or more of methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate.
4. The polyacrylate/silicone hybrid pressure sensitive adhesive according to claim 2, wherein the alkyl (meth) acrylate of component (a1) is a mixture of one or more of butyl (meth) acrylate, methyl (meth) acrylate, isooctyl (meth) acrylate.
5. The polyacrylate/silicone hybrid pressure-sensitive adhesive according to claim 1, wherein component (a1) is 80-99% by weight of component (A), and component (a2) is 1-20% by weight of component (A).
6. The polyacrylate/silicone hybrid pressure-sensitive adhesive according to claim 1, wherein (a1) is present in an amount of 90 to 97% by weight of component (A) and component (a2) is present in an amount of 3 to 10% by weight of component (A).
7. The polyacrylate/organosilicon hybrid pressure-sensitive adhesive according to claim 1, wherein both ends of the multifunctional organosiloxane capable of free radical polymerization in component (B) contain acrylate double bonds capable of free radical polymerization, the structural formula is shown as formula (II), the molecular weight is 100-5000, and R1 is alkyl; r2 is methyl or H; r3 is a methyl group or a phenyl group,
wherein R1 is alkyl; r2 is methyl or H; r3 is a methyl group or a phenyl group,
the weight percentage of the component (B) in the acrylate/organic silicon hybrid pressure-sensitive adhesive is 1-10%.
8. The polyacrylate/silicone hybrid pressure sensitive adhesive according to claim 1, wherein the radical photoinitiator of component (C) is one or a mixture of 2, 2-dimethoxy-2-phenylacetophenone (BDK), 1-hydroxycyclohexyl phenyl ketone (184), 2-hydroxy-2-methyl-1-phenylpropan-1-one (1173), 2 (or 4) -Isopropyl Thioxanthone (ITX)2,4, 6-trimethylbenzoyl diphenylphosphine oxide (TPO), bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide (819).
9. The polyacrylate/organosilicon hybrid pressure-sensitive adhesive according to claim 1, wherein the free radical photoinitiator of component (C) is present in an amount of 0.001-5.0 wt% based on the weight of the acrylate/organosilicon hybrid pressure-sensitive adhesive.
10. The polyacrylate/organosilicon hybrid pressure-sensitive adhesive according to claim 1, wherein the antioxidant of component (D) is one or more of antioxidant 1010, antioxidant 1076, antioxidant CA, antioxidant 164, antioxidant 168, antioxidant DNP, antioxidant DLTP, antioxidant TNP, antioxidant TPP, antioxidant MB and antioxidant 264, and the weight percentage of component (D) in the acrylate/organosilicon hybrid pressure-sensitive adhesive is 0.05-5.0%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210559127.1A CN114989731A (en) | 2022-05-22 | 2022-05-22 | Polyacrylate/organic silicon hybrid pressure-sensitive adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210559127.1A CN114989731A (en) | 2022-05-22 | 2022-05-22 | Polyacrylate/organic silicon hybrid pressure-sensitive adhesive |
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| Publication Number | Publication Date |
|---|---|
| CN114989731A true CN114989731A (en) | 2022-09-02 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210559127.1A Pending CN114989731A (en) | 2022-05-22 | 2022-05-22 | Polyacrylate/organic silicon hybrid pressure-sensitive adhesive |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117384557A (en) * | 2023-11-01 | 2024-01-12 | 南雄市沃太化工有限公司 | Low-temperature-resistant polyacrylate pressure-sensitive adhesive and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013213206A (en) * | 2012-03-08 | 2013-10-17 | Sekisui Chem Co Ltd | Transparent substrate treatment method, and pressure-sensitive adhesive for transparent substrate treatment |
| CN103484042A (en) * | 2013-10-11 | 2014-01-01 | 北京天山新材料技术股份有限公司 | Ultraviolet-curable high temperature resistant pressure-sensitive adhesive and preparation method thereof |
| KR20190005538A (en) * | 2017-07-07 | 2019-01-16 | 동우 화인켐 주식회사 | Adhesive composition, protective film and display device using the same |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013213206A (en) * | 2012-03-08 | 2013-10-17 | Sekisui Chem Co Ltd | Transparent substrate treatment method, and pressure-sensitive adhesive for transparent substrate treatment |
| CN103484042A (en) * | 2013-10-11 | 2014-01-01 | 北京天山新材料技术股份有限公司 | Ultraviolet-curable high temperature resistant pressure-sensitive adhesive and preparation method thereof |
| KR20190005538A (en) * | 2017-07-07 | 2019-01-16 | 동우 화인켐 주식회사 | Adhesive composition, protective film and display device using the same |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117384557A (en) * | 2023-11-01 | 2024-01-12 | 南雄市沃太化工有限公司 | Low-temperature-resistant polyacrylate pressure-sensitive adhesive and preparation method thereof |
| CN117384557B (en) * | 2023-11-01 | 2024-04-09 | 南雄市沃太化工有限公司 | Low-temperature-resistant polyacrylate pressure-sensitive adhesive and preparation method thereof |
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