CN110819258A - Pressure-sensitive adhesive polymer and preparation method thereof, and pressure-sensitive adhesive product and preparation method thereof - Google Patents
Pressure-sensitive adhesive polymer and preparation method thereof, and pressure-sensitive adhesive product and preparation method thereof Download PDFInfo
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- CN110819258A CN110819258A CN201911068163.2A CN201911068163A CN110819258A CN 110819258 A CN110819258 A CN 110819258A CN 201911068163 A CN201911068163 A CN 201911068163A CN 110819258 A CN110819258 A CN 110819258A
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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
- 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
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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
- C09J11/08—Macromolecular additives
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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
- C09J139/00—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Adhesives based on derivatives of such polymers
- C09J139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C09J139/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
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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
- C09J7/10—Adhesives in the form of films or foils without carriers
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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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
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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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- 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
- C09J2493/00—Presence of natural resin
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention provides a pressure-sensitive adhesive polymer and a preparation method thereof, and a pressure-sensitive adhesive product and a preparation method thereof. The pressure-sensitive adhesive polymer is obtained by polymerizing a plurality of raw material components, wherein the raw material components comprise acrylate monomers; a copolymerizable monomer selected from at least two of a hydroxyl-containing monomer, a carboxyl-containing monomer, and a nitrogen-containing monomer; an initiator; the mass-average molecular weight Mz of the pressure-sensitive adhesive polymer is 120-150 ten thousand g/mol, and the molecular weight distribution is less than or equal to 2. The pressure-sensitive adhesive product containing the pressure-sensitive adhesive polymer has good buffering effect, does not need to add a foaming material, and can realize lightness and thinness.
Description
Technical Field
The invention relates to the technical field of adhesives, and particularly discloses a pressure-sensitive adhesive polymer and a pressure-sensitive adhesive product.
Background
At present, with the arrival of the full screen era and even the foldable era of the mobile phone and the establishment of the 5G-initiated everything interconnection era, the screen application scenes are more and more, the glass panels used by the mobile phone are larger and larger, the thickness of the glass panels is thinner and thinner, and the probability of breakage after the mobile phone falls off in the use process is also larger and larger. The present invention also provides some beneficial adhesive tape inventions, such as foam adhesive tapes made of base materials such as PE, PU, and acryl, VHB adhesive tapes made by 3M company, etc., wherein the pressure-sensitive adhesive products (e.g., pressure-sensitive adhesive tapes) provide better buffering effect by means of foaming voids generated by the base materials made of foam or the adhesives themselves or by means of adding hollow microspheres, etc.
However, in terms of improving the buffering and anti-falling effects by using an acrylate adhesive or a rubber adhesive, polymer foam particles, glass microspheres and an expandable polymer are added inside the adhesive or gas is filled into the adhesive to form bubbles, and then the adhesive is coated to form an adhesive film, so that the adhesive film has good buffering and anti-falling effects due to the existence of the bubbles. However, the addition of the foaming particles, the glass microspheres, the expandable polymer and the like seriously controls the addition ratio, the size and the number of foam pores, the stability of each process and the dispersion of the additives are difficult, the process is complex, and the production cost is high, and meanwhile, due to the existence of the additives, the requirement on the thickness of a final adhesive layer is met, and the lower limit of the thickness of the current mainstream is basically more than 100 micrometers.
For the adoption of the method that the adhesive layer is coated on the foam base material layer, and the effect of falling resistance is achieved through the buffering effect of the foam base material layer, two gluing procedures are needed for manufacturing the double-sided tape, so that the processing efficiency is reduced, and the cost is increased; in addition, the multi-layer structure cannot meet the requirement of thinning, and the total thickness is difficult to be controlled below 100 μm on the premise of ensuring the high-viscosity high-buffering effect.
Therefore, the above pressure-sensitive adhesive articles inevitably have a problem that the thickness is generally thick with a good cushion effect, and the total thickness of the adhesive tape is generally 100 μm or more. Therefore, it is important to develop a light and thin pressure-sensitive adhesive product to improve the cushioning and drop-resistant effects.
Disclosure of Invention
It is an object of the present invention to overcome the deficiencies of the prior art and it is an object of the present invention to provide a pressure sensitive adhesive polymer which solves the problem of the prior art process of using a pressure sensitive adhesive article to improve the balance between cushioning and drop resistance and thickness of the pressure sensitive adhesive article.
It is another object of the present invention to provide a process for the preparation of the pressure sensitive adhesive polymer as described above and as detailed below.
It is another object of the present invention to provide a pressure sensitive adhesive article as described above and as detailed below.
It is another object of the present invention to provide a method of making a pressure sensitive adhesive article as described above and in detail below.
In order to achieve the above objects and other objects, the present invention includes the following technical solutions: the pressure-sensitive adhesive polymer is obtained by polymerizing a plurality of raw material components, wherein the raw material components comprise acrylate monomers; a copolymerizable monomer selected from at least two of a hydroxyl-containing monomer, a carboxyl-containing monomer, and a nitrogen-containing monomer; an initiator; the mass-average molecular weight Mz of the pressure-sensitive adhesive polymer is 120-150 ten thousand g/mol, and the molecular weight distribution is less than or equal to 2.
In one embodiment of the present invention, the raw material component comprises 50 to 90% by weight of the acrylate monomer and 10 to 50% by weight of the copolymerizable monomer.
In one embodiment of the present invention, the content of the nitrogen-containing monomer is equal to or less than 16% by weight based on the weight of the monomer component of the pressure-sensitive adhesive polymer, and the nitrogen-containing monomer is grafted to the terminal of the pressure-sensitive adhesive polymer.
The invention also discloses a preparation method of the pressure-sensitive adhesive polymer, which comprises the following steps of providing a plurality of raw material components, wherein the raw material components comprise acrylate monomers, comonomers and initiators, and the comonomers are selected from at least two of hydroxyl-containing monomers, carboxyl-containing monomers and nitrogen-containing monomers; and carrying out a polymerization step on the raw materials to obtain the pressure-sensitive adhesive polymer with the mass-average molecular weight Mz of 120-150 ten thousand g/mol and the molecular weight distribution of less than or equal to 2.
In one embodiment of the present invention, the polymerizing step includes subjecting the plurality of raw material components to a plurality of feeding processes, and/or a plurality of heating processes.
In one embodiment of the present invention, the multiple temperature raising process includes a first-stage temperature and a second-stage temperature, and the second-stage temperature is higher than the first-stage temperature within a range of 2 to 10 ℃.
In one embodiment of the present invention, the pressure sensitive adhesive polymer is prepared by solvent polymerization.
The present invention also provides a pressure sensitive adhesive article comprising a base layer; a pressure-sensitive adhesive layer disposed on a surface of the base layer, the pressure-sensitive adhesive layer comprising a pressure-sensitive adhesive polymer; the pressure-sensitive adhesive polymer is obtained by polymerizing a plurality of raw material components, wherein the mass-average molecular weight Mz of the pressure-sensitive adhesive polymer is 150 ten-thousand g/mol, the molecular weight distribution is less than or equal to 2, and the raw material components comprise acrylate monomers; a copolymerizable monomer selected from at least two of a hydroxyl-containing monomer, a carboxyl-containing monomer, and a nitrogen-containing monomer; and (3) an initiator.
In one embodiment of the present invention, the pressure-sensitive adhesive layer further comprises a tackifier.
In one embodiment of the present invention, the tackifying resin is present in an amount less than 15 weight percent based on the weight of the pressure sensitive adhesive layer.
In one embodiment of the present invention, the pressure-sensitive adhesive layer further comprises a curing agent.
In one embodiment of the present invention, the curing agent is an isocyanate-based curing agent or an epoxy-based curing agent.
In one embodiment of the present invention, the thickness of the pressure-sensitive adhesive layer is 30 to 80 μm.
The invention also provides a preparation method of the pressure-sensitive adhesive product, which comprises the following steps: providing a base layer; forming a pressure-sensitive adhesive layer on a surface of the base layer, the pressure-sensitive adhesive layer comprising a pressure-sensitive adhesive polymer; the pressure-sensitive adhesive polymer is obtained by polymerizing a plurality of raw material components, wherein the mass-average molecular weight Mz of the pressure-sensitive adhesive polymer is 150 ten-thousand g/mol, the molecular weight distribution is less than or equal to 2, and the raw material components comprise acrylate monomers; a copolymerizable monomer selected from at least two of a hydroxyl-containing monomer, a carboxyl-containing monomer, and a nitrogen-containing monomer; and (3) an initiator.
In one embodiment of the present invention, the pressure-sensitive adhesive layer is formed on the surface of the base layer by a solvent coating method.
In summary, the present invention provides a pressure-sensitive adhesive polymer and a pressure-sensitive adhesive article. According to the preparation method of the pressure-sensitive adhesive polymer provided by the invention, the molecular weight of the pressure-sensitive adhesive polymer is accurately controlled and the molecular weight distribution range is controllable by adopting a mode of carrying out multiple feeding processes and multiple heating processes on multiple raw material components, the mass average molecular weight Mz of the pressure-sensitive adhesive polymer is 150 ten thousand g/mol, and the molecular weight distribution is less than or equal to 2. In addition, the invention grafts the nitrogen-containing monomer at the end of the pressure-sensitive adhesive polymer to provide strong intermolecular force, and the main chain forms a regular long molecular chain structure by the preparation method as described above and described in detail below, so that the pressure-sensitive adhesive product formed by the pressure-sensitive adhesive polymer of the invention on the surface of the base layer by a solvent coating method has good buffer effect, can provide good anti-falling effect without adding foaming materials (such as foaming particles, elastomer microspheres and the like), and can realize lightness and thinness. Other features, benefits and advantages will be apparent from the disclosure including the description and claims detailed herein.
Drawings
FIG. 1 shows a flow chart for the preparation of one embodiment of the method of the present invention for preparing a pressure sensitive adhesive polymer.
FIG. 2 shows a schematic structural view of one embodiment of a pressure sensitive adhesive article of the present invention.
FIG. 3 shows a schematic view of an apparatus for drop testing of a pressure sensitive adhesive article of the present invention.
Detailed Description
The present invention is further illustrated below with reference to specific examples, which are intended to be illustrative only and not to limit the scope of the invention.
Referring to fig. 1 to 3, the present invention is described in detail, and other advantages and effects of the present invention will be easily understood by those skilled in the art from the disclosure of the present specification. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
The term "acrylate monomer" in the present invention generally refers to an acrylate monomer and/or a methacrylate monomer.
The term "acrylic acid" in the present invention means acrylic acid and/or methacrylic acid.
The term "pressure-sensitive adhesive polymer" in the present invention means a polymer obtained by polymerizing an acrylate monomer and/or a methacrylate monomer as a main monomer component, and the term "acrylate polymer" may be used interchangeably.
Pressure-sensitive adhesive polymer and preparation method thereof
Referring to FIG. 1, one embodiment of a method for preparing a pressure-sensitive adhesive polymer is provided, including but not limited to the following steps S1-S2. Step S1: providing a feedstock composition comprising: an acrylate monomer; a copolymerizable monomer selected from at least two of a hydroxyl-containing monomer, a carboxyl-containing monomer, and a nitrogen-containing monomer; and (3) an initiator.
Examples of the acrylate monomer may be C1-C18 alkyl acrylate, and further, may be C3-C10 cycloalkyl, such as methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, butyl acrylate, isobutyl acrylate, t-butyl acrylate, hexyl acrylate, etc.; C3-C8 cycloalkyl acrylates such as cyclopropyl acrylate, cyclobutyl acrylate, cyclopentyl acrylate, cyclohexyl acrylate, and the like; C6-C12 aryl acrylates such as phenyl acrylate, naphthyl acrylate, and the like; C1-C18 alkyl methacrylate, further, may be C3-C10 cycloalkyl such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, isopropyl methacrylate, butyl methacrylate, isobutyl methacrylate, t-butyl methacrylate, hexyl methacrylate, etc.; C3-C8 cycloalkyl methacrylates such as cyclopropyl methacrylate, cyclobutyl methacrylate, cyclopentyl methacrylate, cyclohexyl methacrylate, and the like; or C6-C12 aryl methacrylates, such as phenyl methacrylate, naphthyl methacrylate, and the like, wherein the C1-C18 alkyl, C3-C8 cycloalkyl, and C6-C12 aryl groups can be substituted with one or more substituents independently selected from hydroxy, amino, carboxy, epoxy, or C3-C8 cycloalkyl optionally substituted with hydroxy, amino, carboxy, or epoxy, C6-C12 aryl, or C6-C12 aryloxy. Specific examples include Butyl Acrylate (BA), Methyl Acrylate (MA), and methyl methacrylate. The acrylate monomer is present as a major monomer component, and the polymer includes 50 to 90 wt% of the acrylate monomer and 10 to 50 wt% of the copolymerizable monomer. That is, the content of the acrylate monomer is 50 to 90% by weight, further, for example, may be 70 to 90% by weight, based on the total amount of the monomer components constituting the acrylate polymer. For example 70 wt.%, 80 wt.%, 85 wt.%, 90 wt.%.
Among the copolymerizable monomers, the hydroxyl group-containing monomer may be, for example, hydroxy C1-C10 alkyl acrylates, such as 2-hydroxyethyl acrylate (HEA), 3-hydroxypropyl acrylate, and 4-hydroxybutyl acrylate; hydroxy C1-C10 alkyl acrylamides, for example, 2-hydroxyethyl acrylamide or 3-hydroxypropyl acrylamide; and ethoxylated hydroxyethyl methacrylate.
Among the copolymerizable monomers, the carboxyl group-containing monomer may be, for example, acrylic acid, itaconic acid, maleic acid, fumaric acid, crotonic acid and isocrotonic acid, and anhydrides thereof, such as maleic anhydride.
Among the copolymerizable monomers, the nitrogen-containing monomer may be, for example, N-vinyl-2-pyrrolidone, acryloylmorpholine, N-vinylpyridine, N-vinylpiperidone, N-vinylpyrimidine, N-vinylpiperazine, N-vinylpyrrole, N-vinylimidazole, aminoethyl acrylate, dimethylaminoethyl acrylate, and tert-butylaminoethyl acrylate. The nitrogen-containing monomer is grafted to the end of the acrylate polymer and is unreactive with curing agents involved in the process of preparing pressure sensitive adhesive articles. According to the invention, the nitrogen-containing monomer is grafted on the tail end of the acrylate polymer, so that strong intermolecular force is provided, the regular long molecular chain structure is formed on the main chain by the preparation method, and the pressure-sensitive adhesive product containing the structure realizes high buffer performance without adding foaming materials such as foaming particles, elastomer microspheres and the like, so that the thickness of an adhesive film is effectively reduced. The nitrogen-containing monomer is present in a proportion of not more than 16% by weight, further, for example, not more than 14%, such as 8%, 9%, 12%, based on the total amount of monomer components of the polymer, from the viewpoint of improving the cushion performance and the drop resistance of a pressure-sensitive adhesive article comprising the acrylate polymer.
The presence of the copolymerizable monomer as a monomer component may contribute to an increase in adhesive strength of the pressure-sensitive adhesive layer and/or have higher cohesive strength. The comonomer is selected from at least two of hydroxyl-containing monomer, carboxyl-containing monomer and nitrogen-containing monomer, and further the comonomer is selected from the combination of hydroxyl-containing monomer, carboxyl-containing monomer and nitrogen-containing monomer. Examples thereof include a combination of acrylic acid, 2-hydroxyethyl acrylate (HEA), and N-vinyl-2-pyrrolidone. The polymer includes 50 to 90 weight percent of the acrylate monomer and 10 to 50 weight percent of the copolymerizable monomer. That is, the copolymerizable monomer is contained in an amount of 10 to 50% by weight, further, for example, 10 to 30% by weight, for example, 10%, 15%, 20%, 30% by weight, based on the total amount of the monomer components constituting the acrylate-based polymer.
The starting components of the pressure sensitive adhesive polymer of the present invention comprise an initiator for initiating polymerization of the acrylate monomer and the copolymerizable monomer to form the acrylate polymer. The selection of the initiator type can be actually selected according to different polymerization methods, for example, a thermal initiator is used in the thermal initiation process, a photoinitiator is used in the photo initiation process, and any initiator capable of initiating the polymerization of the acrylate monomer and the copolymerizable monomer to form the acrylate polymer should be covered in the scope of the present invention. For example, the acrylate polymer is thermally initiated, and in particular, can be obtained, for example, by means of radical polymerization, solvent polymerization, and emulsion polymerization. Solvent polymerization is employed in view of improving controllability of the molecular weight and molecular weight distribution of the polymer, and the initiator of the solvent polymerization may be, for example, an azo-type initiator such as Azobisisobutyronitrile (AIBN), Azobisisoheptonitrile (ABVN); peroxide initiators, such as Benzoyl Peroxide (BPO); redox initiators such as ammonium persulfate/ferrous sulfate, ammonium persulfate/sodium bisulfite initiators. The amount of the initiator is, for example, 0.1 to 4%, further, for example, 0.1 to 2%, relative to the total amount of all the polymerization monomers, i.e., based on the weight of the monomer component of the pressure-sensitive adhesive polymer, and the initiator may be optionally supplemented according to the degree and need of the actual reaction.
The solvent for the solvent polymerization may be, for example, an ester, an alcohol, a ketone, a carboxylic acid, an aliphatic hydrocarbon, a cycloalkane, etc., and specifically, for example, ethyl acetate, n-butanol, acetone, acetic acid, benzene, toluene, ethylbenzene, cumene, tert-butylbenzene, heptane, cyclohexane. Further, for example, ethyl acetate.
Referring next to fig. 1, the method for preparing the pressure-sensitive adhesive polymer of the present invention further includes step S2: subjecting the plurality of raw material components in step S1 to a polymerization step to obtain the pressure-sensitive adhesive polymer.
In step S2, the polymerizing step includes subjecting the plurality of raw material components to a multiple feed process. Specifically, in the production process of the present invention, for example, in the process of solvent polymerization, for example, the following are added sequentially: a solution containing acrylate monomers and dissolving sufficiently for a period of time. For example 10 to 30 minutes; then adding a solution containing an initiator to initiate polymerization of the acrylate monomer, and reacting for a period of time, for example, 2-4 hours; then, the copolymerizable monomer is added, and the reaction is continued until the reaction is completed, for example, 4 to 12 hours, for example, 6 to 10 hours. Further, the copolymerizable monomer also participates in the reaction by stepwise feeding, for example, sequentially adding the solution containing the carboxyl group-containing monomer, and reacting for a period of time, for example, 1 to 3 hours; then adding a solution containing hydroxyl monomers, and reacting for a period of time, for example, 1-3 hours; then, a solution containing a nitrogen-containing monomer is added to react until the reaction is finished, for example, for 2 to 4 hours. Of course, for example, the carboxyl-containing monomer and the hydroxyl-containing monomer may be added to the reaction system at the same time, followed by the addition of the nitrogen-containing monomer, specifically, the solution containing the carboxyl-containing monomer and the hydroxyl-containing monomer may be added sequentially, and after a certain period of reaction, the reaction may be carried out for a certain period of time, for example, 2 to 5 hours, for example, 3 hours; then, a solution containing a nitrogen-containing monomer is added to react until the reaction is finished, for example, for 3 to 6 hours. Furthermore, the step-by-step feeding process further comprises gradually adding the raw material components into the reaction system, for example, dropwise adding a solution containing the initiator into the system, and adding the solution in portions, for example, 2 to 4 times, each for 10 to 30 minutes.
In step S2, the polymerizing step includes subjecting the plurality of raw material components to a plurality of temperature increasing processes. Specifically, the multiple temperature raising processes include a first-stage temperature raising process and a second-stage temperature raising process, wherein the temperature after the second-stage temperature raising process is higher than the temperature after the first-stage temperature raising process within a range of 2-10 ℃, further within a range of 2-5 ℃, such as 2 ℃,3 ℃ and 5 ℃, specifically, the temperature of the first stage is 76-80 ℃, and the temperature of the second stage is 78-82 ℃, 79-83 ℃ and 81-85 ℃. Specifically, in a specific embodiment disclosed by the invention, acrylate (BA) and ethyl acetate are added into a three-neck flask reaction vessel with a condensation pipe, wherein the reaction vessel is provided with a stirring device, the speed of the stirring device is adjustable, the solution is heated to 76-80 ℃ while stirring, Azodiisobutyronitrile (AIBN) diluted by ethyl acetate is added by titration under stirring for 2-3 times, 15-30 min is added every time at intervals of 20-40 min, after 2 hours of constant temperature reaction, ethyl acetate of Acrylic Acid (AA), 2-hydroxyethyl acrylate (HEA) is added, the reaction temperature is raised by 2 ℃ again, then the reaction temperature is kept for 3 hours, 0.2-0.6 g of Azodiisobutyronitrile (AIBN) diluted by ethyl acetate and 5-9 g of N-vinyl-2-pyrrolidone are added, after 240 minutes of reaction, and adding 40-80 g of ethyl acetate so as to dilute the polymer to proper viscosity, and cooling and taking liquid after the reaction is finished, thus obtaining the acrylate adhesive polymer. According to the invention, the multiple raw material components are subjected to multiple feeding processes and/or multiple heating processes, the pressure-sensitive adhesive polymer obtained by polymerization has uniform molecular weight and narrow molecular weight step by step, the mass-average molecular weight Mz is 150-ten thousand g/mol, such as 120-ten-thousand g/mol, 125-ten-thousand g/mol and 140-ten-thousand g/mol, and the molecular weight distribution is less than or equal to 2, such as 1.8, 1.6, 1.5, 1.2 and 1.1. Further, 1.8 or less and 1.2 or less. The pressure-sensitive adhesive product obtained from the ideal pressure-sensitive adhesive polymer obtained by the preparation method has good buffering effect, does not need to add a foaming material, and can realize lightness and thinness.
Pressure sensitive adhesive articles and methods of making the same
Referring to fig. 2, the present invention also provides a pressure-sensitive adhesive article 1 comprising a base layer 10 and a pressure-sensitive adhesive layer 20.
Referring next to fig. 2, the base layer 10 is a carrier of the pressure-sensitive adhesive article for supporting and protecting the pressure-sensitive adhesive layer, the base layer 10 may be, for example, cellophane/film, PCK release paper/film, laminated paper/film, polyester (e.g., PET) film, polypropylene film, etc., and further, the base layer 10 may further include polyester, polyamide, etc., such as polyethylene terephthalate (PET) film, Polyimide (PI) film, etc. The thickness of the base layer 10 is 40-75 μm, for example 50, 75 μm.
Referring next to fig. 2, the pressure-sensitive adhesive layer 20 is disposed on the surface of the base layer 10, and the pressure-sensitive adhesive layer 20 includes the pressure-sensitive adhesive polymer obtained by the above-mentioned preparation method of the pressure-sensitive adhesive polymer. The pressure-sensitive adhesive polymer is a main component of the pressure-sensitive adhesive layer 20, and the content of the pressure-sensitive adhesive polymer is in the range of 50 to 100% by weight, further in the range of 60 to 90% by weight, such as 70% by weight, 80% by weight, 85% by weight, based on the weight of the pressure-sensitive adhesive layer 20.
Further, the pressure-sensitive adhesive layer 20 may further include a tackifier, which is a rosin-modified tackifier resin such as rosin resin, rosin acid and its modified products such as rosin ester, methyl ester of rosin acid, triethylene glycol ester of rosin acid, glycerol ester of rosin acid, pentaerythritol ester of rosin acid, in an amount of less than 25 wt%, for example, 22 wt%, 19 wt%, 16 wt%, 10 wt%, based on the weight of the pressure-sensitive adhesive layer 20, in terms of enhancing the adhesion effect of the pressure-sensitive adhesive layer 20. Further, less than 20 wt%.
Further, the pressure-sensitive adhesive layer 20 may further include a curing agent, and the pressure-sensitive adhesive layer 20 formed of the pressure-sensitive adhesive polymer of the present invention is a two-pack type adhesive, thereby improving the drop resistance of the pressure-sensitive adhesive article in terms of improving cohesive strength, the curing agent being an isocyanate type curing agent or an epoxy type curing agent. Further, the isocyanate-based curing agent includes, for example, aliphatic, cycloaliphatic, aliphatic-cycloaliphatic, aromatic, aliphatic-aromatic and/or cycloaliphatic-aromatic isocyanates, further, aliphatic and aromatic isocyanates, and specific examples thereof may be exemplified by hexamethylene diisocyanate, octamethylene diisocyanate, decamethylene diisocyanate, dodecamethylene diisocyanate, tetramethylene diisocyanate, trimethylhexane diisocyanate, tetramethylhexane diisocyanate, isophorone diisocyanate (IPDI), 2-isocyanatopropylcyclohexyl isocyanate, dicyclohexylmethane 2,4 '-diisocyanate, dicyclohexylmethane 4,4' -diisocyanate, 1, 4-or 1, 3-bis (isocyanatomethyl) cyclohexane, 1, 4-or 1, 3-or 1, 2-isocyanatocyclohexanes and 2, 4-or 2, 6-diisocyanato-1-methylcyclohexane, dimers and trimers thereof. The epoxy-type curing agent includes, for example, aliphatic amines, alicyclic amines, aromatic amines, polyamides, acid anhydrides, resins, and tertiary amine epoxy curing agents. The content of the curing agent is less than 5%, preferably less than 3%, and further preferably less than 2%, based on the weight of the pressure-sensitive adhesive layer 20.
The present invention also provides a method of making a pressure sensitive adhesive article as described above, the method comprising:
-providing a substrate 10;
-forming a pressure sensitive adhesive layer 20 on the surface of the base layer 10, wherein the pressure sensitive adhesive layer 20 comprises a pressure sensitive adhesive polymer.
Further, the pressure-sensitive adhesive layer 20 may further include a tackifier and/or a curing agent. The pressure-sensitive adhesive layer 20 may be formed on the surface of the base layer 10 by, for example, a solvent coating method. Specifically, the pressure-sensitive adhesive polymer, the tackifier and/or the curing agent are stirred and mixed in the solvent to form a mixed solution, the mixed solution is coated on the surface of the base layer 10, and the solvent is dried and removed. The viscosity of the mixed solution is 800-4000cp.s, such as 800cp.s, 900cp.s, 950cp.s and 4000 cp.s. The coating effect is excellent within the above range. The solvent may be, for example, an ester, an alcohol, a ketone, a carboxylic acid, an aliphatic hydrocarbon, a cycloalkane, etc., and specifically, for example, ethyl acetate, n-butanol, acetone, acetic acid, benzene, toluene, ethylbenzene, cumene, tert-butylbenzene, heptane, cyclohexane. Further, the solvent is the same as the solvent selected in the preparation of the pressure-sensitive adhesive polymer in view of improving solubility and maintaining a desired viscosity. Such as ethyl acetate.
The dry film thickness of the pressure-sensitive adhesive layer 20 is usually in the range of 30-80 μm, further, in the range of 30-50 μm, the pressure-sensitive adhesive product provided by the invention has a good buffering effect, a good drop-resistant effect can be provided without adding a foaming material (such as foaming particles, elastomer microspheres and the like), according to a drop impact resistance test, the pressure-sensitive adhesive product provided by the invention is attached between a PC plate and an aluminum plate, for example, and the drop-resistant frequency is more than 50 times. And the thickness of the pressure-sensitive adhesive product is less than 100 mu m, so that the light and thin effect is realized.
Device assembly
In addition, a device assembly is provided on which the pressure sensitive adhesive article is located. The device component may be, for example, an electronic device widely used in the market, such as a smart phone, a PAD, a PMP, a car navigation device, an MP3 player, a tablet computer, a notebook computer, and further, the device component is located on a substrate of a device component, such as a glass panel.
Examples
Example 1
A three-neck flask reaction vessel with a condenser tube was charged with 78g of acrylate BA and 10g of ETAC, the solution was heated to 76 ℃ with stirring, 1g of 0.2% AIBN diluted with ethyl acetate was added dropwise with stirring, 15min each time at intervals of 30min, and after 2hr of isothermal reaction, 4gAA, 12g of 2-hydroxyethyl acrylate (HEA), 60g of ethyl acetate were added, the temperature was raised to 78 ℃ and maintained for 180min, 0.5g of 0.2% AIBN diluted with ethyl acetate and 6g of N-vinyl-2-pyrrolidone were added, and after 240min of isothermal reaction, 50g of ethyl acetate was added to dilute to an appropriate viscosity, and after completion of the reaction, the temperature was lowered to obtain a solution.
Taking 50g of the synthesized acrylate adhesive, adding 50g of acetic acid and 8g of tackifying resin KE-100, stirring for 15min, then adding 0.6g of L-75, then coating on a 25 mu mPE release film, drying by an oven to form a glue film with the thickness of 50 mu m, and attaching by using the 50 mu mPE release film, wherein the release film is selected from Vancun optotechnologies, Inc. of Yangzhou.
Example 2
Adding 78g of acrylate BA and 10g of ETAC into a three-neck flask reaction vessel with a condensation pipe, heating the solution to 78 ℃ while stirring, then adding 1.5g of 0.2% AIBN diluted by ethyl acetate in a dropwise manner while stirring, adding the mixture in 2 portions at intervals of 20min for 40min, reacting at constant temperature for 2hr, adding 6gAA, 10g of 2-hydroxyethyl acrylate (HEA) and 60g of ethyl acetate, raising the temperature to 80 ℃ for 180min, adding 0.3g of 0.2% AIBN diluted by ethyl acetate and 8g of N-vinyl-2-pyrrolidone, reacting at constant temperature for 240min, adding 60g of ethyl acetate to dilute the mixture to a proper viscosity, and cooling the mixture to obtain the liquid after the reaction is finished.
Taking 50g of the synthesized acrylate adhesive, adding 50g of acetic acid and 11g of tackifying resin KE-100, stirring for 15min, then adding 0.6g of L-75, then coating on a 25 mu mPE release film, drying by an oven to form a glue film with the thickness of 50 mu m, and attaching by using the 50 mu mPE release film, wherein the release film is selected from Vancun optotechnologies, Inc. of Yangzhou.
Example three:
adding 78g of acrylate BA and 10g of ETAC into a three-neck flask reaction vessel with a condensation pipe, heating the solution to 78 ℃ while stirring, then adding 1.5g of 0.2% AIBN diluted by ethyl acetate in a dropwise manner while stirring, adding the mixture in 2 portions at intervals of 20min for 40min, reacting at constant temperature for 2hr, adding 8gAA, 8g of 2-hydroxyethyl acrylate (HEA) and 60g of ethyl acetate, raising the temperature to 80 ℃ for 180min, adding 0.3g of 0.2% AIBN diluted by ethyl acetate and 12g of N-vinyl-2-pyrrolidone, reacting at constant temperature for 240min, adding 60g of ethyl acetate to dilute the mixture to a proper viscosity, and cooling the mixture to obtain the liquid after the reaction is finished.
Taking 50g of the synthesized acrylic adhesive, adding 50g of acetic acid and 11g of tackifying resin KE-100, stirring for 15min, then adding 0.6g of L-75, then coating on a 25 mu mPE release film, drying by an oven to form a glue film with the thickness of 50 mu m, and attaching by using the 50 mu mPE release film, wherein the release film is selected from Vancun optotechnologies, Inc. of Yangzhou.
Test method
The pressure-sensitive adhesive articles obtained in examples 1 to 3 were subjected to the adhesion test, holding power test and drop test described below, and the test results are shown in table 1.
And (3) testing adhesive force: testing SUS plate with surface roughness less than 10nm and sample width 25mm, attaching under 23 deg.C x 50% RH environment, rolling with 2Kg roller for 3 times, standing for 20min, peeling at 300mm/min and 180 deg.C, and recording test result.
And (3) testing the retention force: testing an SUS plate, wherein the surface roughness of the SUS plate is less than 10nm, the attachment area is 25mm multiplied by 25mm, a 2Kg roller is used for rolling for 10 times to and fro, after the SUS plate is placed in an oven at the temperature of 85 ℃ for 20min, a weight of 1Kg is loaded at 180 degrees, 1Hr is hung, and the moving distance is recorded;
and (3) drop test: the adhesive film is cut into a frame with the width W73 mm, the length L113m and the thickness of 0.7mm, the frame is attached between a PC board and an aluminum board, water-sensitive test paper 100 is attached between the PC board and the aluminum board, the PC board is 78mm, 118mm and 2mm in size, after the frame is attached, the frame is pressed for 10s by 5kg of pressure, then the frame is placed for 48h, then the frame is freely dropped from the height of 1m in the 6-plane direction, each edge of the frame is dropped for 50 times, whether the board is separated or not is judged, the test device shown in the figure 3 can be used for judging the separation mode, specifically, after the board is placed in the water depth of 1m for 10min, whether water enters or not is judged, and whether the color of the water-sensitive test paper 100 placed in the middle of the board.
In summary, the present invention provides a pressure-sensitive adhesive polymer and a pressure-sensitive adhesive article. According to the preparation method of the pressure-sensitive adhesive polymer provided by the invention, the molecular weight of the pressure-sensitive adhesive polymer is accurately controlled and the molecular weight distribution range is controllable by adopting a mode of carrying out multiple feeding processes and multiple heating processes on multiple raw material components, the mass average molecular weight Mz of the pressure-sensitive adhesive polymer is 150 ten thousand g/mol, and the molecular weight distribution is less than or equal to 2. In addition, the invention grafts the nitrogenous monomer at the tail end of the pressure-sensitive adhesive polymer to provide strong intermolecular force, and the main chain forms a regular long molecular chain structure through a stepwise polymerization method, so that the pressure-sensitive adhesive product formed by the pressure-sensitive adhesive polymer of the invention on the surface of the base layer through a solvent coating method has good buffer effect, can provide good anti-falling effect without adding foaming materials (such as foaming particles, elastomer microspheres and the like), and can realize lightness and thinness. Therefore, the present invention has high industrial utility value.
The foregoing embodiments are merely illustrative of the principles and utilities of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or change the above-mentioned embodiments without departing from the spirit and scope of the present invention. Accordingly, it is intended that all equivalent modifications or changes which can be made by those skilled in the art without departing from the spirit and technical spirit of the present invention be covered by the claims of the present invention.
Claims (15)
1. A pressure sensitive adhesive polymer, wherein the pressure sensitive adhesive polymer is obtained by polymerizing a plurality of raw material components, the raw material components comprising:
an acrylate monomer;
a copolymerizable monomer selected from at least two of a hydroxyl-containing monomer, a carboxyl-containing monomer, and a nitrogen-containing monomer;
an initiator;
the mass-average molecular weight Mz of the pressure-sensitive adhesive polymer is 120-150 ten thousand g/mol, and the molecular weight distribution is less than or equal to 2.
2. The pressure sensitive adhesive polymer of claim 1 wherein the raw components comprise 50 to 90 weight percent of the acrylate monomer and 10 to 50 weight percent of the copolymerizable monomer.
3. The pressure-sensitive adhesive polymer according to claim 1, wherein the nitrogen-containing monomer is present in an amount of 16 wt.% or less based on the weight of the monomer component of the pressure-sensitive adhesive polymer, and the nitrogen-containing monomer is grafted to the terminal of the pressure-sensitive adhesive polymer.
4. A method of making a pressure sensitive adhesive polymer comprising the steps of:
providing a plurality of feedstock components comprising an acrylate monomer, a comonomer, and an initiator, wherein the comonomer is selected from at least two of a hydroxyl-containing monomer, a carboxyl-containing monomer, and a nitrogen-containing monomer;
and carrying out a polymerization step on the raw materials to obtain the pressure-sensitive adhesive polymer with the mass-average molecular weight Mz of 120-150 ten thousand g/mol and the molecular weight distribution of less than or equal to 2.
5. The method of claim 4, wherein the step of polymerizing comprises subjecting the plurality of raw material components to a plurality of feeding processes and/or a plurality of heating processes.
6. The method of claim 5 wherein the multiple temperature ramp process comprises a first stage temperature and a second stage temperature, the second stage temperature being in the range of 2-10 ℃ higher than the first stage temperature.
7. The method for preparing the pressure-sensitive adhesive polymer according to any one of claims 4 to 5, wherein the pressure-sensitive adhesive polymer is prepared by solvent polymerization.
8. A pressure sensitive adhesive article, wherein the pressure sensitive adhesive article comprises:
a base layer;
a pressure-sensitive adhesive layer disposed on a surface of the base layer, the pressure-sensitive adhesive layer comprising a pressure-sensitive adhesive polymer;
the pressure-sensitive adhesive polymer is obtained by polymerizing a plurality of raw material components, wherein the mass-average molecular weight Mz of the pressure-sensitive adhesive polymer is 150 ten-thousand g/mol, the molecular weight distribution is less than or equal to 2, and the raw material components comprise acrylate monomers; a copolymerizable monomer selected from at least two of a hydroxyl-containing monomer, a carboxyl-containing monomer, and a nitrogen-containing monomer; and (3) an initiator.
9. The pressure-sensitive adhesive article of claim 8 wherein the pressure-sensitive adhesive layer further comprises a tackifier.
10. The pressure sensitive adhesive article of claim 9 wherein the tackifying resin is present in an amount less than 15 weight percent based on the weight of the pressure sensitive adhesive layer.
11. The pressure sensitive adhesive article of claim 8 wherein the pressure sensitive adhesive layer further comprises a curing agent.
12. The pressure sensitive adhesive article of claim 11 wherein the curing agent is an isocyanate-based curing agent or an epoxy-based curing agent.
13. The pressure-sensitive adhesive article of claim 8 wherein the pressure-sensitive adhesive layer has a thickness of 30 to 80 μm.
14. A method of making a pressure sensitive adhesive article comprising the steps of:
providing a base layer;
forming a pressure-sensitive adhesive layer on a surface of the base layer, the pressure-sensitive adhesive layer comprising a pressure-sensitive adhesive polymer;
the pressure-sensitive adhesive polymer is obtained by polymerizing a plurality of raw material components, wherein the mass-average molecular weight Mz of the pressure-sensitive adhesive polymer is 150 ten-thousand g/mol, the molecular weight distribution is less than or equal to 2, and the raw material components comprise acrylate monomers; a copolymerizable monomer selected from at least two of a hydroxyl-containing monomer, a carboxyl-containing monomer, and a nitrogen-containing monomer; and (3) an initiator.
15. The method of claim 14, wherein the pressure-sensitive adhesive layer is formed on the surface of the base layer by a solvent coating method.
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