CN112625176A - Solvent-tolerant acrylate composition and application thereof - Google Patents

Solvent-tolerant acrylate composition and application thereof Download PDF

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CN112625176A
CN112625176A CN202110015575.0A CN202110015575A CN112625176A CN 112625176 A CN112625176 A CN 112625176A CN 202110015575 A CN202110015575 A CN 202110015575A CN 112625176 A CN112625176 A CN 112625176A
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acrylate
monomer
composition
solvent
parts
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CN112625176B (en
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顾正青
秦健
周奎任
陈启峰
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Suzhou Shihua New Material Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • 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
    • C09J133/18—Homopolymers or copolymers of nitriles
    • C09J133/20—Homopolymers or copolymers of acrylonitrile
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/18—Homopolymers or copolymers of nitriles
    • C08J2333/20—Homopolymers or copolymers of acrylonitrile
    • 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
    • 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
    • C09J2467/00—Presence of polyester
    • C09J2467/006—Presence of polyester in the substrate

Abstract

The invention discloses a solvent-tolerant acrylate composition and application thereof. The prepared adhesive film is applied to acrylate pressure-sensitive adhesive, can resist permeation of polar and non-polar solvents at a bonding interface, and can be applied to places with more chemical solvents.

Description

Solvent-tolerant acrylate composition and application thereof
The present application is a divisional application of the invention patent application having an application date of 2020, 1/17, application No. 202010051394.9, entitled "a solvent-resistant acrylate composition and use thereof".
Technical Field
The invention relates to an acrylate composition and application thereof, in particular to an acrylate composition using a multifunctional phosphorus hydroxyl compound as a cross-linking agent and application thereof in an adhesive film.
Background
Pressure sensitive adhesives, commonly known as stickers, are commonly used in the manufacture of pressure sensitive tapes, pressure sensitive labels, and the like. The pressure-sensitive adhesive is known as a pressure-sensitive adhesive, and generally only requires finger pressure to achieve a quick adhesive effect without staining or damaging the bonded surfaces.
Generally classified into rubber pressure-sensitive adhesives, acrylate pressure-sensitive adhesives, silicone pressure-sensitive adhesives, polyurethane pressure-sensitive adhesives, and the like according to categories. The acrylate pressure-sensitive adhesive has the advantages of good pressure-sensitive adhesion effect and the like due to the viscoelastic property and good weather resistance of the polymer, and can be widely used for manufacturing pressure-sensitive adhesive tapes with different application requirements, such as electronic components in equipment such as mobile phones, tablets, computers and the like, without adding other additives such as tackifying resin and the like. Along with the expansion of the application range, the requirement on the chemical solvent resistance of the pressure-sensitive adhesive tape is more and more strict. The chemical solvents which are tolerated include not only polar solvents such as ethanol, isopropanol, etc., but also nonpolar solvents such as oleic acid, epoxidized soybean oil, sun cream, etc.
Patent CN 107849412a describes that nitrile rubber can resist the attack of oily solvent, but it is known that rubber pressure sensitive adhesive has poor resistance to light, heat aging, etc., and a tackifying resin needs to be added for use. The traditional acrylate pressure-sensitive adhesive has poor tolerance to polar solvents and non-polar solvents, and cannot meet the requirements of electronic components.
Patent CN 108699415 describes that the use of short-chain methyl acrylate monomer can enhance the oil resistance, but the resistance effect still can not achieve the desired result. In addition, patents have described the use of tertiary carbonates, long chain acrylate monomers, 2-hydroxyethyl methacrylate phosphate monomers as functional monomers to enhance solvent resistance. However, the price of the monomer is high, and the synthesis process of the 2-hydroxyethyl methacrylate phosphate ester monomer is complex.
The use of a vinyl epoxy monomer copolymerized with an acrylate monomer for enhancing the solvent resistance of acrylate pressure-sensitive adhesives is described by Nile et al, but gelation occurs during synthesis and satisfactory performance cannot be obtained.
The prior art starts from the aspect of monomer tolerance, and solvent-tolerant acrylate pressure-sensitive adhesive is synthesized. The pressure-sensitive adhesive may have strong solvent resistance, but the solvent resistance cannot be completely solved because the solvent invasion of the adhesive tape joint interface cannot be solved.
Disclosure of Invention
In view of the above problems, an object of the present invention is to provide a solvent-tolerant acrylate composition and an application thereof in an adhesive film, wherein the solvent-tolerant acrylate composition is applied to an acrylate pressure-sensitive adhesive film to prepare a chemical solvent-tolerant pressure-sensitive adhesive tape, which can tolerate the permeation of polar and non-polar solvents at the bonding interface and can be used in places with more chemical solvents.
In order to achieve the purpose, the invention adopts the following technical scheme.
A solvent-tolerant acrylate composition is prepared from soft monomer, hard monomer, functional monomer and free radical initiator through free radical polymerizing reaction, and cross-linking reaction with cross-linking agent. Furthermore, the components of the composition do not contain tackifying resin, so that the hidden danger of dissolution or swelling of the acrylate composition in a solvent caused by using tackifying resin (such as rosin resin, terpene resin and the like) is overcome, and the solvent resistance of the whole acrylate composition is improved.
As a preferable scheme of the scheme, the soft monomer is a monomer with a glass transition temperature of-70 ℃ to-20 ℃, and further at least one of butyl acrylate, isooctyl acrylate and ethyl acrylate can be selected.
In a preferred embodiment of the present invention, the hard monomer is a monomer having a glass transition temperature greater than 0 ℃, and further at least one of methyl (meth) acrylate, styrene, acrylonitrile, and acrylamide may be used.
As a preferred embodiment of this embodiment, the functional monomer is an epoxy acrylate monomer, further preferably glycidyl (meth) acrylate, which provides an epoxy group for a cross-linkable reaction for cross-linking with the multifunctional phosphorus hydroxy compound.
In a preferred embodiment of the present invention, the radical initiator is at least one of azobisisobutyronitrile and benzoyl peroxide.
As a preferable scheme of the scheme, the cross-linking agent is a multifunctional phosphorus hydroxyl cross-linking agent; further, the polyfunctional phosphorus hydroxyl crosslinking agent is preferably phosphoric acid. Phosphoric acid can provide more phosphorus hydroxyl groups, the phosphorus hydroxyl groups can be subjected to crosslinking reaction with epoxy groups in glycidyl acrylate, the phosphorus hydroxyl groups are excessive relative to epoxy groups, after the crosslinking reaction, unreacted phosphorus hydroxyl groups are still contained in the acrylate composition, the acrylate composition is adhered to the surface of a base material and has better wettability, micropores on the surface of the adhered base material can be reduced, moisture, grease and the like on the surface of the base material are removed, and therefore the chemical solvent resistance is improved.
As a preferred embodiment of this embodiment, the crosslinking reaction is a solution polymerization process and can be carried out at 20 to 110 ℃. The organic solvent in the polymerization reaction process can be at least one of ethyl acetate, toluene and butyl acetate.
The application also discloses an application of the composition in an adhesive film, and the adhesive film and a bonding interface of an object to be pasted can tolerate the permeation of a solvent, and particularly can tolerate the permeation of a polar solvent and a non-polar solvent.
As a preferred scheme of the scheme, the adhesive film is an acrylate composition adhesive film, and the components in parts by weight are as follows: 40-80 parts of soft monomer, 20-50 parts of hard monomer, 1-10 parts of functional monomer, 0.1-1 part of free radical initiator, 0.1-5 parts of multifunctional phosphorus hydroxyl compound cross-linking agent and 100-200 parts of organic solvent. .
And (3) synthesizing the acrylate polymer solution by using a solution polymerization method, adding the multifunctional phosphorus hydroxyl compound crosslinking agent into the acrylate composition solution, uniformly mixing, coating and drying to obtain the adhesive film.
Compared with the prior art, the invention has the following advantages.
(1) The solvent-tolerant acrylate composition has excellent ageing resistance of acrylate glue, and can achieve good bonding force without adding tackifying resin.
(2) The adhesive film prepared from the solvent-tolerant acrylate composition contains unreacted phosphorus hydroxyl, is adhered to the surface of a base material, has better wettability, can reduce micropores on the surface of the adhered base material, and removes water, grease and the like on the surface of the base material, thereby increasing the tolerance of a chemical solvent.
(3) The raw materials are easy to obtain, the preparation method is simple, and the method is suitable for large-scale production, popularization and application.
Detailed Description
The technical solutions in the present invention will be described clearly and completely with reference to the following detailed description, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments.
Example 1.
The acrylate polymer is prepared by the following steps: adding 50g of ethyl acetate into a reaction kettle, heating to 60 ℃, introducing nitrogen for 10 minutes, and dropwise adding a mixed monomer solution, wherein the mixed monomer solution is as follows: 50g of butyl acrylate, 26.5g of isooctyl acrylate, 15g of methyl methacrylate, 5g of acrylonitrile, 3.5g of glycidyl methacrylate and 0.4g of Benzoyl Peroxide (BPO), wherein the dropwise addition is completed within 4-6 hours, 50g of ethyl acetate is added, the reaction is continued for 4-5 hours, and then the reaction is finished, and the reaction is diluted by 50g of ethyl acetate to obtain the acrylate polymer with the solid content of 40%.
Solvent-tolerant acrylate composition solution preparation: taking 25g of the above acrylate polymer, adding 0.25g of phosphoric acid, mixing uniformly, and carrying out crosslinking reaction to obtain the acrylic ester polymer. And coating the solvent-tolerant acrylate composition solution on a PET (polyethylene terephthalate) substrate, and drying for 3 minutes at 110 ℃ to obtain a solvent-tolerant adhesive film which can be used as an acrylate pressure-sensitive adhesive.
Example 2.
The acrylate polymer is prepared by the following steps: 50g of toluene/ethyl acetate mixed solution (1: 1 mass ratio) is added into a reaction kettle, the temperature is raised to 70 ℃, nitrogen is introduced for 10 minutes, and a mixed monomer solution is dropwise added, wherein the mixed monomer solution is as follows: 58.5g of isooctyl acrylate, 20g of methyl acrylate, 5g of methyl methacrylate, 9g of styrene, 1.5g of glycidyl methacrylate, 6g of acrylonitrile and 0.4g of Azobisisobutyronitrile (AIBN), wherein the dropwise addition is completed within 4-6 hours, 50g of a toluene/ethyl acetate mixed solution (1: 1 mass ratio) is added, the reaction is continued for 4-5 hours, and then the reaction is completed, and the reaction is diluted by 50g of ethyl acetate, so that the acrylate pressure-sensitive adhesive (acrylate polymer) with the solid content of 40% is obtained.
Taking 25g of the acrylate pressure sensitive adhesive (acrylate polymer), adding 0.1g of phosphoric acid, and uniformly mixing. Coating on a PET substrate and drying for 3 minutes at 110 ℃ to obtain the chemical resistance pressure-sensitive adhesive tape.
Comparative example.
The preparation method comprises the following steps: adding 50g of ethyl acetate into a reaction kettle, heating to 80 ℃, introducing nitrogen for 10 minutes, and dropwise adding a mixed monomer solution, wherein the mixed monomer solution is as follows: 50g of butyl acrylate, 28g of isooctyl acrylate, 15g of methyl methacrylate, 2g of acrylic acid, 5g of acrylonitrile and 0.4g of Benzoyl Peroxide (BPO) were reacted in the same manner as in example 1.
25g of the product is taken, 0.1g of L-75 curing agent is added and mixed evenly. Coating on a PET substrate and drying for 3 minutes at 110 ℃ to obtain the pressure-sensitive adhesive tape.
The pressure-sensitive adhesive tapes prepared in the above examples and comparative examples were cut to a width of 5mm, attached to an SUS304 plate, immersed in ethanol and oleic acid as chemical solvents, left at 60 ℃ and 95RH for 72 hours, then taken out, wiped with a surface solvent, left at room temperature for 2 hours, and then tested for 180 ° peel force, and the peel force decay of a blank sample was used as an evaluation standard, and the data are shown in the following table.
Figure 510555DEST_PATH_IMAGE001
。
Comparing the above test results, the scheme (example 1, example 2) has a peel force retention rate of more than 58.9% after the oleic acid soaking, and the prior art (comparative) has a peel force retention rate of only 22.9%, which shows that the application has significant grease resistance. The present solutions (example 1, example 2) had peel force retention greater than 54.4% after ethanol soaking and the prior art (comparative) had only 19.9% peel force retention, indicating significant alcohol resistance in this application.
The scope of the present invention is not limited thereto, and any person skilled in the art can substitute or change the technical solution of the present invention and the inventive concept within the technical scope of the present invention.

Claims (8)

1. A solvent-tolerant acrylate composition is prepared by carrying out free radical polymerization reaction on a soft monomer, a hard monomer, a functional monomer and a free radical initiator, and then carrying out crosslinking reaction on the mixture and a crosslinking agent, and is characterized in that:
the components do not contain tackifying resin,
the functional monomer is an epoxy acrylate monomer,
the cross-linking agent is a multifunctional phosphorus hydroxyl cross-linking agent,
the solvent-tolerant acrylate composition contains unreacted phosphorus hydroxyl groups.
2. The composition of claim 1, wherein: the soft monomer is at least one of butyl acrylate, isooctyl acrylate and ethyl acrylate.
3. The composition of claim 1, wherein: the hard monomer is at least one of methyl (meth) acrylate, styrene, acrylonitrile and acrylamide.
4. The composition of claim 1, wherein: the free radical initiator is at least one of azodiisobutyronitrile and benzoyl peroxide.
5. The composition of claim 1, wherein: the multifunctional phosphorus hydroxyl crosslinking agent is phosphoric acid.
6. The composition of claim 1, wherein: the crosslinking reaction is carried out at 20-110 ℃.
7. Use of the composition according to any one of claims 1 to 6 in an adhesive film, the adhesive interface of which with an adherend is resistant to penetration by solvents.
8. Use of the composition according to claim 7 in adhesive films, characterized in that: the adhesive film comprises the following components in parts by weight: 40-80 parts of soft monomer, 20-50 parts of hard monomer, 1-10 parts of functional monomer, 0.1-1 part of free radical initiator and 200 parts of organic solvent are subjected to free radical polymerization reaction, and then are uniformly mixed with 0.1-5 parts of cross-linking agent, and then are coated and dried to obtain the high-performance polyurethane resin.
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