CN116004153A - High-viscosity antistatic solvent type acrylic ester pressure-sensitive adhesive and preparation method thereof - Google Patents
High-viscosity antistatic solvent type acrylic ester pressure-sensitive adhesive and preparation method thereof Download PDFInfo
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- CN116004153A CN116004153A CN202211721116.5A CN202211721116A CN116004153A CN 116004153 A CN116004153 A CN 116004153A CN 202211721116 A CN202211721116 A CN 202211721116A CN 116004153 A CN116004153 A CN 116004153A
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Abstract
The invention provides a high-viscosity antistatic solvent type acrylic pressure-sensitive adhesive, which comprises the following components: 20-40% of soft monomer; 1-10% of hard monomer; 1-5% of functional monomer by mass; 5-15% of antistatic monomer; 0.25 to 0.8 percent of initiator; 40% -60% of solvent by mass; the antistatic monomer includes a hydrophilic group. The invention also relates to a preparation method thereof; through intensive research on the characteristics of functional groups of special monomers, the pressure-sensitive adhesive has antistatic characteristics, and is prepared into an excellent high-viscosity antistatic product, so that the quality and the safety of the product are greatly improved.
Description
Technical Field
The invention relates to the field of pressure-sensitive adhesives, in particular to a high-viscosity antistatic solvent type acrylate pressure-sensitive adhesive and a preparation method thereof.
Background
Most of solvent type acrylic ester pressure-sensitive adhesive products are high molecular materials, are excellent electric insulating materials, and have large surface resistivity (10) 14 -10 17 Ω/≡), a large amount of static electricity is easy to generate, the harm is very large in the safe production process, and the serious accidents such as fire and explosion are caused. There are two methods of current stage treatment: one is to use antistatic liquid to carry out coating treatment on raw materials (polyester film), the other is to add special auxiliary agent with antistatic property into pressure-sensitive adhesive, and the purpose is to reduce the surface resistivity of the product to 10 11 The disadvantage of below Ω/≡is that the two methods have high cost, long production period and poor product quality. The patent of publication No. CN105153976B discloses an antistatic pressure-sensitive adhesive, wherein the antistatic effect is achieved by using an additive polyelectrolyte, and the acrylic resin has no antistatic effect, and has the advantages of larger addition amount, high cost and poor weather resistance; the patent of publication No. CN108753196A discloses an antistatic high-temperature-resistant acrylate pressure-sensitive adhesive, a preparation method and application thereof, and the antistatic effect is also achieved by virtue of an additive polyelectrolyte, and the acrylic resin does not have the antistatic effect.
Therefore, it is necessary to design a product with antistatic property to produce excellent high-viscosity antistatic product, and the quality and safety of the product are greatly improved.
Disclosure of Invention
In order to overcome the defects in the prior art, the first object of the invention is to provide a high-viscosity antistatic solvent type acrylate pressure-sensitive adhesive, which comprises the following components:
the antistatic monomer includes a hydrophilic group.
Preferably, the hydrophilic group is methoxy.
Preferably, the antistatic monomer is monoethyl adipate.
Preferably, the soft monomer is at least one of alkyl acrylates having a glass transition temperature below-30 ℃.
Preferably, the hard monomer is at least one of alkyl acrylates having a glass transition temperature greater than-30 ℃.
Preferably, the functional monomer is at least one of hydroxyl group-containing or carboxyl group-containing acrylic functional monomers.
Preferably, the initiator is at least one of benzoyl peroxide, azobisisobutyronitrile and azobisisoheptonitrile.
Preferably, the solvent is at least one of toluene, ethyl acetate, butyl acetate and butanone.
The second object of the invention is to provide a preparation method of the high-viscosity antistatic solvent type acrylate pressure-sensitive adhesive, which comprises the following steps:
step one: adding 20% -40% of soft monomer, 1% -10% of hard monomer, 1% -5% of functional monomer, 5% -15% of antistatic monomer and 40% -60% of solvent into a reaction kettle, and introducing nitrogen for 20 minutes at 66-67 ℃ under stirring;
step two: adding 0.05% -0.2% of first-stage initiator, and keeping the temperature for reaction for 2 hours;
step three: adding 0.1% -0.3% of second-stage initiator, and keeping the temperature for reaction for 2 hours at 73-75 ℃;
step four: adding 0.1% -0.3% of a third-stage initiator, and keeping the temperature for reaction for 3 hours at 75-80 ℃;
step five: cooling and adding 5-20% solvent to obtain the high-viscosity antistatic acrylate pressure-sensitive adhesive.
Compared with the prior art, the invention has the beneficial effects that: the invention provides a high-viscosity antistatic solvent type acrylic pressure-sensitive adhesive, which comprises the following components: 20-40% of soft monomer; 1-10% of hard monomer; 1-5% of functional monomer by mass; 5-15% of antistatic monomer; 0.25 to 0.8 percent of initiator; 40% -60% of solvent by mass; the antistatic monomer includes a hydrophilic group. The invention also relates to a preparation method thereof; through intensive research on the characteristics of functional groups of special monomers, the pressure-sensitive adhesive has antistatic characteristics, and is prepared into an excellent high-viscosity antistatic product, so that the quality and the safety of the product are greatly improved.
The foregoing description is only an overview of the present invention, and is intended to provide a better understanding of the present invention, as it is hereinafter described in more detail with reference to the preferred embodiments of the present invention. Specific embodiments of the present invention are given in detail by the following examples.
Detailed Description
The present invention will be further described with reference to the following specific embodiments, and it should be noted that, on the premise of no conflict, new embodiments may be formed by any combination of the embodiments or technical features described below.
With the increasing market of electronic components, glass materials, stainless steel plates, various alloy steel plates, plastic raw materials and the like, the demand of solvent type acrylic acid ester pressure-sensitive adhesive products is continuously increased, and as the harm caused by static electricity in production and life is more and more obvious, excellent antistatic performance is urgently needed for the solvent type acrylic acid ester pressure-sensitive adhesive products. In order to overcome the defects of the existing protective film, the invention relates to a high-viscosity antistatic solvent type acrylic pressure-sensitive adhesive, which comprises the following components:
the antistatic monomer includes a hydrophilic group. Through intensive research on the characteristics of the functional groups of the special monomers, the pressure-sensitive adhesive has antistatic characteristics, and is prepared into an excellent high-viscosity antistatic product, so that the quality and the safety of the product are greatly improved.
In some embodiments, in order to have a significant impact on the antistatic performance of the pressure sensitive adhesive, the hydrophilic groups may be hydroxyl, methoxy, ethoxy, carboxyl, and other common hydrophilic groups; preferably, the hydrophilic group is methoxy, which can significantly improve the antistatic effect of the pressure-sensitive adhesive. When the hydrophilic group is hydroxyl, the antistatic monomer can be hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, and the like.
When the hydrophilic group is ethoxy, the antistatic monomer can be carbopol acrylate, 2-ethoxyethyl acrylate, 3-ethoxyethyl acrylate, and the like.
When the hydrophilic group is a carboxyl group, the antistatic monomer may be acrylic acid, methacrylic acid, butenoic acid, or the like.
When the antistatic monomer is monoethyl adipate, the antistatic effect can be effectively improved by using the content of monoethyl adipate, and the surface resistivity of the pressure-sensitive adhesive is obviously reduced along with the increase of the dosage of monoethyl adipate from 5% to 15%; when the dosage of the monoethyl adipate is 15%, the surface resistivity of a product prepared by the pressure-sensitive adhesive is as follows: not more than 10 10 Ω/≡; 0.3% antistatic agent, surface resistivity: not more than 10 9 Ω/≡ (glue line thickness: 25 μm).
When the hydrophilic group is methoxy, the antistatic monomer can be adipic acid monoethyl ester, 1, 6-hexanediol methoxy monoacrylate, methoxy ethyl methacrylate and the like. In some embodiments, to further enhance the antistatic effect, the antistatic monomer is monoethyl adipate.
The invention has antistatic property on the acrylic resin itself, and no polymer electrolyte is added. It should be appreciated that the high-tack antistatic pressure sensitive adhesive may be matched with an antistatic agent to further enhance antistatic effect; the polymer electrolyte can be added in small amount to improve the antistatic effect, but the dosage is obviously smaller.
In some embodiments, the soft monomer is at least one of alkyl acrylates having a glass transition temperature of less than-30 ℃; specifically, it may be 2-ethylhexyl acrylate, butyl acrylate, ethyl acrylate, or the like.
In some embodiments, the hard monomer is at least one of an alkyl acrylate having a glass transition temperature greater than-30 ℃. Specifically, it may be acrylamide, methyl methacrylate, methyl acrylate, or the like.
In some embodiments, the functional monomer is at least one of an acrylic functional monomer containing a hydroxyl group or a carboxyl group; specifically, it may be hydroxyethyl acrylate, 4-hydroxybutyl acrylate, acrylic acid, or the like.
In some embodiments, the initiator is at least one of benzoyl peroxide, azobisisobutyronitrile, azobisisoheptonitrile.
In some embodiments, the solvent is at least one of toluene, ethyl acetate, butyl acetate, butanone.
The invention also relates to a preparation method of the high-viscosity antistatic solvent type acrylic pressure-sensitive adhesive, which comprises the following steps:
step one: adding 20% -40% of soft monomer, 1% -10% of hard monomer, 1% -5% of functional monomer, 5% -15% of antistatic monomer and 40% -60% of solvent into a reaction kettle, and introducing nitrogen for 20 minutes at 66-67 ℃ under stirring;
step two: adding 0.05% -0.2% of first-stage initiator, and keeping the temperature for reaction for 2 hours;
step three: adding 0.1% -0.3% of second-stage initiator, and keeping the temperature for reaction for 2 hours at 73-75 ℃;
step four: adding 0.1% -0.3% of a third-stage initiator, and keeping the temperature for reaction for 3 hours at 75-80 ℃;
step five: cooling and adding 5-20% solvent to obtain the high-viscosity antistatic acrylate pressure-sensitive adhesive. The high-viscosity antistatic pressure-sensitive adhesive starts from the source and achieves an antistatic effect by using an antistatic monomer; in addition, the adhesive property of the high-viscosity product can be met; the prepared protective film has good weather resistance and can adapt to high-temperature and high-humidity environments.
The initiator is added for multiple times respectively, so that the reaction efficiency is improved, and the product quality is improved.
Example 1
37% of isooctyl acrylate, 5% of methyl acrylate, 0.1% of hydroxyethyl acrylate, 2.4% of acrylic acid, 5% of monoethyl adipate and 50% of ethyl acetate are added into an experimental device in percentage by mass. Under the condition of stirring, heating to 66-67 ℃, introducing nitrogen for 20 minutes, adding 0.1% of azodiisobutyronitrile, reacting 2H, adding 0.2% of azodiisobutyronitrile, controlling the temperature to be near 74 ℃, reacting 2H, adding 0.2% of azodiisobutyronitrile, continuing reacting 3H, cooling, and adding a diluting solvent, thus obtaining the target adhesive.
Example two
32% of isooctyl acrylate, 5% of methyl acrylate, 0.1% of hydroxyethyl acrylate, 2.4% of acrylic acid, 10% of monoethyl adipate and 50% of ethyl acetate are added into an experimental device in percentage by mass. Under the condition of stirring, heating to 66-67 ℃, introducing nitrogen for 20 minutes, adding 0.1% of azodiisobutyronitrile, reacting 2H, adding 0.2% of azodiisobutyronitrile, controlling the temperature to be near 74 ℃, reacting 2H, adding 0.2% of azodiisobutyronitrile, continuing reacting 3H, cooling, and adding a diluting solvent, thus obtaining the target adhesive.
Example III
27% of isooctyl acrylate, 5% of methyl acrylate, 0.1% of hydroxyethyl acrylate, 2.4% of acrylic acid, 15% of monoethyl adipate and 50% of ethyl acetate are added into an experimental device in percentage by mass. Under the condition of stirring, heating to 66-67 ℃, introducing nitrogen for 20 minutes, adding 0.1% of azodiisobutyronitrile, reacting 2H, adding 0.2% of azodiisobutyronitrile, controlling the temperature to be near 74 ℃, reacting 2H, adding 0.2% of azodiisobutyronitrile, continuing reacting 3H, cooling, and adding a diluting solvent, thus obtaining the target adhesive.
Example IV
The experimental device is charged with 37.25% of isooctyl acrylate, 5% of methyl acrylate, 0.1% of hydroxyethyl acrylate, 2.4% of acrylic acid, 5% of monoethyl adipate and 50% of ethyl acetate by mass percent. Under the condition of stirring, heating to 66-67 ℃, introducing nitrogen for 20 minutes, adding 0.05% of azodiisobutyronitrile, reacting 2H, adding 0.1% of azodiisobutyronitrile, controlling the temperature to be near 74 ℃, reacting 2H, adding 0.1% of azodiisobutyronitrile, continuing reacting 3H, cooling, and adding a diluting solvent, thus obtaining the target adhesive.
Example five
36.7% of isooctyl acrylate, 5% of methyl acrylate, 0.1% of hydroxyethyl acrylate, 2.4% of acrylic acid, 5% of monoethyl adipate and 50% of ethyl acetate are added into an experimental device in percentage by mass. Under the condition of stirring, heating to 66-67 ℃, introducing nitrogen for 20 minutes, adding 0.2% of azodiisobutyronitrile, reacting 2H, adding 0.3% of azodiisobutyronitrile, controlling the temperature to be near 74 ℃, reacting 2H, adding 0.3% of azodiisobutyronitrile, continuing reacting 3H, cooling, and adding a diluting solvent, thus obtaining the target adhesive.
Comparative example one
42% of isooctyl acrylate, 5% of methyl acrylate, 0.1% of hydroxyethyl acrylate, 2.4% of acrylic acid and 50% of ethyl acetate are added into an experimental device in mass percent. Under the condition of stirring, heating to 66-67 ℃, introducing nitrogen for 20 minutes, adding 0.1% of azodiisobutyronitrile, reacting 2H, adding 0.2% of azodiisobutyronitrile, controlling the temperature to be near 74 ℃, reacting 2H, adding 0.2% of azodiisobutyronitrile, continuing reacting 3H, cooling, and adding a diluting solvent, thus obtaining the target adhesive.
Comparative example two
The experimental device is charged with 40% of isooctyl acrylate, 5% of methyl acrylate, 0.1% of hydroxyethyl acrylate, 2.4% of acrylic acid, 2% of monoethyl adipate and 50% of ethyl acetate by mass percent. Under the condition of stirring, heating to 66-67 ℃, introducing nitrogen for 20 minutes, adding 0.1% of azodiisobutyronitrile, reacting 2H, adding 0.2% of azodiisobutyronitrile, controlling the temperature to be near 74 ℃, reacting 2H, adding 0.2% of azodiisobutyronitrile, continuing reacting 3H, cooling, and adding a diluting solvent, thus obtaining the target adhesive.
Comparative example three
The experimental device is charged with the weight percent of 22% of isooctyl acrylate, 5% of methyl acrylate, 0.1% of hydroxyethyl acrylate, 2.4% of acrylic acid, 20% of monoethyl adipate and 50% of ethyl acetate. Under the condition of stirring, heating to 66-67 ℃, introducing nitrogen for 20 minutes, adding 0.1% of azodiisobutyronitrile, reacting 2H, adding 0.2% of azodiisobutyronitrile, controlling the temperature to be near 74 ℃, reacting 2H, adding 0.2% of azodiisobutyronitrile, continuing reacting 3H, cooling, and adding a diluting solvent, thus obtaining the target adhesive.
Comparative example four
The experimental device was charged with 37% by mass of isooctyl acrylate, 5% by mass of methyl acrylate, 2.5% by mass of acrylic acid, 5% by mass of hydroxyethyl acrylate and 50% by mass of ethyl acetate. Under the condition of stirring, heating to 66-67 ℃, introducing nitrogen for 20 minutes, adding 0.1% of azodiisobutyronitrile, reacting 2H, adding 0.2% of azodiisobutyronitrile, controlling the temperature to be near 74 ℃, reacting 2H, adding 0.2% of azodiisobutyronitrile, continuing reacting 3H, cooling, and adding a diluting solvent, thus obtaining the target adhesive.
Comparative example five
37% of isooctyl acrylate, 5% of methyl acrylate, 0.1% of hydroxyethyl acrylate, 2.4% of acrylic acid, 5% of carbomer acrylate and 50% of ethyl acetate are added into an experimental device in percentage by mass. Under the condition of stirring, heating to 66-67 ℃, introducing nitrogen for 20 minutes, adding 0.1% of azodiisobutyronitrile, reacting 2H, adding 0.2% of azodiisobutyronitrile, controlling the temperature to be near 74 ℃, reacting 2H, adding 0.2% of azodiisobutyronitrile, continuing reacting 3H, cooling, and adding a diluting solvent, thus obtaining the target adhesive.
Comparative example six
37% of isooctyl acrylate, 5% of methyl acrylate, 0.1% of hydroxyethyl acrylate, 2.4% of acrylic acid, 5% of methacrylic acid and 50% of ethyl acetate are added into an experimental device in percentage by mass. Under the condition of stirring, heating to 66-67 ℃, introducing nitrogen for 20 minutes, adding 0.1% of azodiisobutyronitrile, reacting 2H, adding 0.2% of azodiisobutyronitrile, controlling the temperature to be near 74 ℃, reacting 2H, adding 0.2% of azodiisobutyronitrile, continuing reacting 3H, cooling, and adding a diluting solvent, thus obtaining the target adhesive.
Comparative example seven
The experimental device was charged with 37% by mass of isooctyl acrylate, 5% by mass of methyl acrylate, 0.1% by mass of hydroxyethyl acrylate, 2.4% by mass of acrylic acid, 5% by mass of methoxyethyl methacrylate and 50% by mass of ethyl acetate. Under the condition of stirring, heating to 66-67 ℃, introducing nitrogen for 20 minutes, adding 0.1% of azodiisobutyronitrile, reacting 2H, adding 0.2% of azodiisobutyronitrile, controlling the temperature to be near 74 ℃, reacting 2H, adding 0.2% of azodiisobutyronitrile, continuing reacting 3H, cooling, and adding a diluting solvent, thus obtaining the target adhesive.
The pressure-sensitive adhesives prepared in examples one to five, comparative examples one to seven were subjected to performance tests, respectively, to obtain the test results of table 1 below.
Condition 1:
examples 1-5 and comparative examples 1-7 were mixed with 0.5% isocyanate curing agent (L-75), coated on 50 μm Polyester (PET) film, and after baking at 110℃for 2min to give a protective film, placed in an electrothermal constant temperature air-blast drying oven at 55℃for 48 hours, and tested for 180℃peel strength.
After testing the surface resistivity of the antistatic protective film, respectively placing the antistatic protective film into an electrothermal constant-temperature blast drying oven at 80 ℃ for 72 hours and a constant-temperature constant-humidity oven at 65 ℃ and humidity of 95% for 72 hours, taking out the antistatic protective film, and testing the surface resistivity of the antistatic protective film and the environmental temperature: 23+ -1deg.C, humidity: 50.+ -. 5%. The test results are shown in Table 1.
Condition 2:
examples 1 to 5 and comparative examples 1 to 7 were mixed with 0.5% of an isocyanate curing agent (L-75) and 0.3% of an antistatic agent HN-TAC-16 (Chemie), coated on a 50 μm Polyester (PET) film, and after baking at 110℃for 2 minutes, a protective film was formed, and placed in an electrothermal constant temperature air-blast drying oven at 55℃for 48 hours to test 180℃peel strength.
After testing the surface resistivity of the antistatic protective film, respectively placing the antistatic protective film into an electrothermal constant-temperature blast drying oven at 80 ℃ for 72 hours and a constant-temperature constant-humidity oven at 65 ℃ and humidity of 95% for 72 hours, taking out the antistatic protective film, and testing the surface resistivity of the antistatic protective film and the environmental temperature: 23+ -1deg.C, humidity: 50.+ -. 5%. The test results are shown in Table 2.
Table 1 table of test results under condition 1
Table 2 table of test results under condition 2
Although embodiments of the present invention have been disclosed above, it is not limited to the details and embodiments shown, it is well suited to various fields of use, and further modifications may be readily made by those skilled in the art without departing from the general concepts defined by the claims and the equivalents thereof, and therefore the invention is not limited to the specific details and examples shown herein.
Claims (9)
1. A high-tack antistatic solvent-type acrylate pressure-sensitive adhesive, comprising:
the antistatic monomer includes a hydrophilic group.
2. The high-adhesion antistatic solvent type acrylate pressure sensitive adhesive according to claim 1 wherein said hydrophilic group is methoxy group.
3. The high-adhesion antistatic solvent type acrylate pressure-sensitive adhesive according to claim 2 wherein the antistatic monomer is monoethyl adipate.
4. The high adhesion antistatic solvent type acrylate pressure sensitive adhesive of claim 1 wherein said soft monomer is at least one of alkyl acrylates having a glass transition temperature below-30 ℃.
5. The high adhesion antistatic solvent type acrylate pressure sensitive adhesive of claim 1 wherein said hard monomer is at least one of alkyl acrylates having a glass transition temperature greater than-30 ℃.
6. The high-adhesion antistatic solvent type acrylate pressure-sensitive adhesive according to claim 1 wherein said functional monomer is at least one of hydroxyl or carboxyl group-containing acrylic functional monomers.
7. The high-adhesion antistatic solvent type acrylate pressure sensitive adhesive of claim 1 wherein the initiator is at least one of benzoyl peroxide, azobisisobutyronitrile, azobisisoheptonitrile.
8. The high-viscosity antistatic solvent type acrylate pressure sensitive adhesive according to claim 1 wherein the solvent is at least one of toluene, ethyl acetate, butyl acetate and butanone.
9. A method for preparing the high-viscosity antistatic solvent type acrylate pressure-sensitive adhesive as claimed in claim 1, comprising the steps of:
step one: adding 20% -40% of soft monomer, 1% -10% of hard monomer, 1% -5% of functional monomer, 5% -15% of antistatic monomer and 40% -60% of solvent into a reaction kettle, and introducing nitrogen for 20 minutes at 66-67 ℃ under stirring;
step two: adding 0.05% -0.2% of first-stage initiator, and keeping the temperature for reaction for 2 hours;
step three: adding 0.1% -0.3% of second-stage initiator, and keeping the temperature for reaction for 2 hours at 73-75 ℃;
step four: adding 0.1% -0.3% of a third-stage initiator, and keeping the temperature for reaction for 3 hours at 75-80 ℃;
step five: cooling and adding 5-20% solvent to obtain the high-viscosity antistatic acrylate pressure-sensitive adhesive.
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| CN202211721116.5A CN116004153A (en) | 2022-12-30 | 2022-12-30 | High-viscosity antistatic solvent type acrylic ester pressure-sensitive adhesive and preparation method thereof |
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