CN111742024A - Adhesive tape - Google Patents
Adhesive tape Download PDFInfo
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- CN111742024A CN111742024A CN201980014238.0A CN201980014238A CN111742024A CN 111742024 A CN111742024 A CN 111742024A CN 201980014238 A CN201980014238 A CN 201980014238A CN 111742024 A CN111742024 A CN 111742024A
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- meth
- acrylate
- adhesive
- adhesive tape
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
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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]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Abstract
The invention provides an adhesive tape which can achieve both excellent adhesive performance and reduced VOC. The adhesive tape of the present invention is an adhesive tape having an adhesive layer containing an adhesive composition. The adhesive composition contains a polymer obtained by copolymerizing a monomer mixture containing (meth) acrylic acid. The thickness of the adhesive layer is 30 [ mu ] m or more. The adhesive tape has total volatile organic compound TVOC concentration of 10000 μ g/m3The TVOC concentration is calculated by using a test piece having an adhesive layer area of 100mm × 100mm and a 5L sample bag.
Description
Technical Field
The present invention relates to an adhesive tape.
Background
In recent years, due to the increase in environmental awareness, it has been required to reduce the amount of Volatile Organic Compounds (VOCs) generated from industrial materials. Such a requirement is particularly significant in the automotive industry, centered around manufacturers having sites in asia, being subject to strict VOC amount management. Therefore, it is also necessary to suppress the VOC amount for an adhesive tape used in automobile manufacturing.
Documents of the prior art
Patent document
Patent document 1 Japanese laid-open patent publication No. 2008-285554
Patent document 2 Japanese patent No. 5142446
Disclosure of Invention
Problems to be solved by the invention
However, it is difficult to reduce the VOC amount while satisfying the performance required for industrial use in the conventional adhesive tape. Accordingly, an object of the present invention is to provide an adhesive tape that can achieve both excellent adhesive performance and a reduction in VOC amount.
Means for solving the problems
Embodiments of the present invention are described below, for example.
[1]An adhesive tape comprising an adhesive layer containing an adhesive composition, wherein the adhesive composition contains a polymer obtained by copolymerizing a monomer mixture containing (meth) acrylic acid, the adhesive layer has a thickness of 30 [ mu ] m or more, and the adhesive tape has a Total Volatile Organic Compound (TVOC) concentration of 10000 [ mu ] g/m3Hereinafter, the Total Volatile Organic Compound (TVOC) concentration was calculated using a test piece having an area of the adhesive layer of 100mm × 100mm and a 5L sampling bag.
[2]According to [1]The adhesive tape, wherein the alcohol concentration calculated using the test piece and the sampling bag is 3000. mu.g/m3The following.
[3]According to [1]Or [2 ]]The adhesive tape, wherein the isoparaffin concentration calculated by using the test piece and the sampling bag is 5000. mu.g/m3The following.
[4] The adhesive tape according to any one of [1] to [3], wherein the content of isoparaffin in the initiator used for copolymerization is 0.03 mass% or less with respect to the total solid content of the adhesive composition.
[5] The adhesive tape according to any one of [1] to [4], wherein the initiator used for the copolymerization contains substantially no isoparaffin.
Effects of the invention
According to the present invention, an adhesive tape that can achieve both excellent adhesive performance and a reduction in VOC amount can be provided.
Detailed Description
Hereinafter, an adhesive tape according to an embodiment of the present invention will be described.
In addition, in the present specification, "polymer" is used in a sense of including a homopolymer and a copolymer, and "polymerization" is used in a sense of including homopolymerization and copolymerization. The compound represented by the formula (i) (i is the formula number) is also simply referred to as "compound (i)". In the present specification, the term (meth) acrylic means acrylic acid or methacrylic acid, the term (meth) acrylate means acrylate or methacrylate, and the term (meth) acryloyl means acryloyl or methacryloyl.
[ adhesive composition ]
The adhesive tape according to one embodiment of the present invention has an adhesive layer containing an adhesive composition. The adhesive composition contains a polymer obtained by copolymerizing a monomer mixture. The adhesive composition is typically an acrylic adhesive composition.
[ Polymer ]
The polymer is obtained by copolymerizing a monomer mixture containing (meth) acrylic acid. By adopting such a configuration, excellent adhesive performance can be achieved.
The total content of (meth) acrylic acid is not particularly limited, and is, for example, 0.5 to 10% by mass, preferably 0.6 to 8% by mass, more preferably 0.7 to 7% by mass, and still more preferably 0.8 to 6% by mass, based on the total mass of all raw material monomers. If the content of (meth) acrylic acid is too large, the VOC amount (particularly, alcohol amount) of the adhesive tape described later becomes high. If the content of (meth) acrylic acid is too small, the effect of adding (meth) acrylic acid as a monomer is slightly weak.
The polymer may be a polymer synthesized by a general radical polymerization method or a polymer synthesized by a living radical polymerization method. The polymer has a weight average molecular weight (Mw) of, for example, 50000 to 3000000, preferably 50000 to 2500000, more preferably 50000 to 2000000, as measured by Gel Permeation Chromatography (GPC). The molecular weight distribution (Mw/Mn) of the polymer as measured by GPC is, for example, 30.0 or less, preferably 25.0 or less, and more preferably 20.0 or less.
The polymer is, for example, a (meth) acrylic polymer. The polymer may be a random polymer or a block polymer. The polymer may be, for example, a (meth) acrylic random polymer or a (meth) acrylic block polymer.
The kind of the monomer other than (meth) acrylic acid that can be contained in the monomer mixture is not particularly limited. As such a monomer, (meth) acrylate is mainly used, but other functional group-containing monomers and copolymerizable monomers may be further used.
(meth) acrylic acid esters
Examples of the (meth) acrylate include alkyl (meth) acrylates, alkoxyalkyl (meth) acrylates, alkoxypolyalkylene glycol mono (meth) acrylates, and (meth) acrylates containing alicyclic groups or aromatic groups. In this case, a functional group-containing (meth) acrylate such as a hydroxyl group-containing (meth) acrylate or a carboxyl group-containing (meth) acrylate is removed from the (meth) acrylate.
The number of carbon atoms of the alkyl group in the alkyl (meth) acrylate is preferably 1 to 20. Examples of the alkyl (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, undecyl (meth) acrylate, lauryl (meth) acrylate, oleyl (meth) acrylate, n-stearyl (meth) acrylate, isostearyl (meth) acrylate, and dodecyl (meth) acrylate.
Examples of the alkoxyalkyl (meth) acrylate include methoxymethyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxypropyl (meth) acrylate, 3-ethoxypropyl (meth) acrylate, 4-methoxybutyl (meth) acrylate, and 4-ethoxybutyl (meth) acrylate.
Examples of the alkoxy polyalkylene glycol mono (meth) acrylate include methoxy diethylene glycol mono (meth) acrylate, methoxy dipropylene glycol mono (meth) acrylate, ethoxy triethylene glycol mono (meth) acrylate, ethoxy diethylene glycol mono (meth) acrylate, and methoxy triethylene glycol mono (meth) acrylate.
Examples of the (meth) acrylate containing an alicyclic group or an aromatic group include cyclohexyl (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, isobornyl (meth) acrylate, and phenoxyethyl (meth) acrylate.
One kind of the (meth) acrylate may be used alone, or two or more kinds may be used. The total amount of the (meth) acrylate used is, for example, 70 to 99.9 mass%, preferably 80 to 99.5 mass%, and more preferably 85 to 98.95 mass% based on the total mass of the total raw material monomers.
Monomer containing functional group
Examples of the functional group-containing monomer other than the (meth) acrylic acid include a hydroxyl group-containing monomer, an acid group-containing monomer, and a nitrogen atom-containing monomer. Examples of the acid group include a carboxyl group, an acid anhydride group, a phosphoric acid group, and a sulfuric acid group. The monomer containing a nitrogen atom includes a nitrogen atom in the form of, for example, an amino group or an amide bond.
Examples of the hydroxyl group-containing monomer include hydroxyl group-containing (meth) acrylates, and specific examples thereof include hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, and 8-hydroxyoctyl (meth) acrylate. The number of carbon atoms of the alkyl group in the hydroxyalkyl (meth) acrylate is usually 2 to 8, preferably 2 to 6.
Examples of the carboxyl group-containing monomer include β -carboxyethyl (meth) acrylate, 5-carboxypentyl (meth) acrylate, mono (meth) acryloyloxyethyl succinate, ω -carboxypolycaprolactone mono (meth) acrylate, itaconic acid, crotonic acid, fumaric acid, and maleic acid. Examples of the acid anhydride group-containing monomer include maleic anhydride. Examples of the phosphoric acid group-containing monomer include (meth) acrylic monomers having a phosphoric acid group in a side chain, and examples of the sulfuric acid group-containing monomer include (meth) acrylic monomers having a sulfuric acid group in a side chain.
Examples of the nitrogen atom-containing monomer include an amino group-containing monomer and an amide bond-containing monomer. Here, the "amino group" is used as a concept including not only a primary amino group but also secondary and tertiary amino groups. The amino group is preferably a tertiary amino group, and the tertiary amino group may be a cyclic amino group. The amide bond may be a part of a lactam structure.
When the amino group-containing monomer contains a secondary or tertiary amino group, the nitrogen atom of the amino group is preferably modified with an alkyl group. Examples of the alkyl group include alkyl groups having 1 to 6 carbon atoms, and specific examples thereof include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, and tert-butyl group.
The amino group-containing monomer is more preferably an aminoalkyl (meth) acrylate. Preferred modes for the amino group in the aminoalkyl (meth) acrylate are the same as those described above. Examples of the alkyl group in the aminoalkyl group include alkyl groups having 1 to 6 carbon atoms, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl. Examples of the aminoalkyl group include a tert-butylaminoethyl group, a dimethylaminoethyl group and a diethylaminoethyl group.
Specific examples of the amino group-containing monomer include t-butylaminoethyl methacrylate (TBAEMA), dimethylaminoethyl methacrylate (DMAEMA; DM), diethylaminoethyl methacrylate (DEAEMA), and dimethylaminoethyl acrylate (DMAEA).
The amide bond-containing monomer is preferably a (meth) acrylamide derivative or a lactam having a vinyl group.
Examples of the (meth) acrylamide derivative include N-alkyl (meth) acrylamides, N-dialkyl (meth) acrylamides, and diacetone acrylamide. Examples of the alkyl group include alkyl groups having 1 to 6 carbon atoms, and specific examples thereof include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, and tert-butyl group.
Specific examples of the amide bond-containing monomer include N, N-Dimethylacrylamide (DMAA), N-Diethylacrylamide (DEAA), N-isopropylacrylamide (NIPAM), Diacetoneacrylamide (DAAM), N-Acryloylmorpholine (ACMO), N-vinyl-2-pyrrolidone (NVP), N-vinyl-caprolactam (NVC), and N- (2-hydroxyethyl) acrylamide (HEAA).
The functional group-containing monomers may be used alone in 1 kind or in 2 or more kinds. The total amount of the functional group-containing monomer other than (meth) acrylic acid is preferably 0 to 15% by mass, and more preferably 0.05 to 10% by mass, based on the total mass of all the raw material monomers.
In the functional group-containing monomer, the total amount of the hydroxyl group-containing polymer is, for example, 0 to 5 mass%, preferably 0.05 to 2 mass%, more preferably 0.1 to 1 mass%, and still more preferably 0.12 to 0.8 mass%, based on the total mass of all the raw material monomers.
(copolymerizable monomer)
Examples of the copolymerizable monomer include alkylstyrene such as styrene, methylstyrene, dimethylstyrene, trimethylstyrene, propylstyrene, butylstyrene, hexylstyrene, heptylstyrene and octylstyrene, styrene-based monomer such as fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, iodostyrene, nitrostyrene, acetylstyrene and methoxystyrene, and vinyl acetate. The copolymerizable monomer may be used alone in 1 kind or in 2 or more kinds.
[ other ingredients ]
The adhesive composition may further contain, as other components, a tackifier resin, a crosslinking agent, a silane coupling agent, an antistatic agent, an organic solvent, an antioxidant, a light stabilizer, a metal corrosion inhibitor, a plasticizer, a crosslinking accelerator, nanoparticles, and the like.
< tackifying resin >
The adhesive composition may contain a tackifier resin. By using a tackifier resin other than the above-mentioned polymer in combination as a component constituting the pressure-sensitive adhesive composition, for example, even an olefin-based adherend such as polyethylene or polypropylene, which is an adherend difficult to adhere to an acrylic pressure-sensitive adhesive in general, can exhibit good adhesiveness (pressure-sensitive adhesiveness). In addition, the constant load peel resistance of the resulting adhesive layer can be improved.
As the tackifier resin, a rosin ester resin is preferably used, and particularly, a polymerized rosin ester resin can be used in combination. As the tackifier resin, for example, a terpene-based tackifier resin or a hydrocarbon petroleum resin can be used.
The tackifier resins may be used alone in 1 kind, or may be used in combination in 2 or more kinds. The total content of the tackifier resin in the adhesive composition is, for example, 1 to 40 parts by mass, preferably 5 to 35 parts by mass, and more preferably 10 to 30 parts by mass, per 100 parts by mass of the polymer.
< crosslinking agent >
Examples of the crosslinking agent include isocyanate compounds, epoxy compounds, and metal chelate compounds.
As the isocyanate-based compound, an isocyanate compound having an isocyanate group of 2 or more in 1 molecule is generally used. Examples of the isocyanate compound include aliphatic diisocyanates, alicyclic diisocyanates, and aromatic diisocyanates. Examples of the aliphatic diisocyanate include aliphatic diisocyanates having 4 to 30 carbon atoms such as ethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, 2-methyl-1, 5-pentane diisocyanate, 3-methyl-1, 5-pentane diisocyanate, and 2, 2, 4-trimethyl-1, 6-hexamethylene diisocyanate. Examples of the alicyclic diisocyanate include alicyclic diisocyanates having 7 to 30 carbon atoms such as isophorone diisocyanate, cyclopentyl diisocyanate, cyclohexyl diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated toluene diisocyanate, hydrogenated diphenylmethane diisocyanate, and hydrogenated tetramethylxylene diisocyanate. Examples of the aromatic diisocyanate include aromatic diisocyanates having 8 to 30 carbon atoms such as phenylene diisocyanate, toluene diisocyanate, xylylene diisocyanate, naphthalene diisocyanate, diphenyl ether diisocyanate, diphenylmethane diisocyanate, and diphenylpropane diisocyanate.
Examples of the isocyanate compound having 3 or more isocyanate groups in 1 molecule include aromatic polyisocyanates, aliphatic polyisocyanates, and alicyclic polyisocyanates. Specific examples thereof include 2, 4, 6-triisocyanate toluene, 1, 3, 5-triisocyanate benzene, and 4, 4' -triphenylmethane triisocyanate. Further, examples of the isocyanate compound include a trimer of diphenylmethane diisocyanate, polymethylene polyphenyl polyisocyanate, a biuret or isocyanurate of hexamethylene diisocyanate or tolylene diisocyanate, a reaction product of trimethylolpropane and tolylene diisocyanate or xylylene diisocyanate (for example, a 3-molecule adduct of tolylene diisocyanate or xylylene diisocyanate), a reaction product of trimethylolpropane and hexamethylene diisocyanate (for example, a 3-molecule adduct of hexamethylene diisocyanate), a polyether polyisocyanate, and a polyester polyisocyanate.
As the epoxy compound, for example, an epoxy compound having 2 or more epoxy groups in 1 molecule is generally used. Examples thereof include ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerol triglycidyl ether, 1, 3-bis (N, N-diglycidylaminomethyl) cyclohexane, N, N, N ', N' -tetraglycidyl-m-xylylenediamine, N, N, N ', N' -tetraglycidylaminophenylmethane, triglycidyl isocyanurate, m-N, N-diglycidylaminophenylglycidyl ether, N, N-diglycidyltoluidine and N, N-diglycidylaniline.
Examples of the metal chelate compound include compounds obtained by coordinating a polyvalent metal such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium, or zirconium with an alkoxide, acetylacetone, or ethyl acetoacetate. Specific examples thereof include aluminum isopropoxide, aluminum sec-butoxide, ethyl aluminum diisopropyl acetoacetate, tris (ethyl acetoacetato) aluminum, and triacetyl aluminum acetonate.
The amount of the crosslinking agent is 0.01 to 10 parts by mass, preferably 0.01 to 8 parts by mass, and more preferably 0.01 to 5 parts by mass, based on 100 parts by mass of the total amount of the crosslinking agent and the polymer. When the crosslinking agent is contained within this range, the balance between the properties of the adhesive can be achieved.
< silane coupling agent >
The silane coupling agent can strongly adhere the pressure-sensitive adhesive layer to an adherend such as a glass substrate in particular, and prevent the peeling of the pressure-sensitive adhesive layer in a high-humidity environment.
Examples of the silane coupling agent include silane coupling agents containing a polymerizable unsaturated group such as vinyltrimethoxysilane, vinyltriethoxysilane, and methacryloxypropyltrimethoxysilane; epoxy group-containing silane coupling agents such as 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane and 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane; amino group-containing silane coupling agents such as 3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane and N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane; halogen-containing silane coupling agents such as 3-chloropropyltrimethoxysilane.
Among them, an epoxy group-containing silane coupling agent is preferable in view of stress relaxation property and the like. In the composition of the present invention, the content of the silane coupling agent is usually 1 part by mass or less, preferably 0.01 to 1 part by mass, and more preferably 0.05 to 0.5 part by mass, per 100 parts by mass of the polymer. When the content is within the above range, the peeling of the adhesive layer in a high-humidity and high-temperature environment and the bleeding of the silane coupling agent in a high-temperature environment tend to be prevented.
< antistatic agent >
Examples of the antistatic agent include surfactants, ionic compounds, and conductive polymers.
Examples of the surfactant include quaternary ammonium salts, amide quaternary ammonium salts, pyridinium salts, and cationic surfactants having a cationic group such as a primary to tertiary amino group; anionic surfactants having an anionic group such as a sulfonate group, a sulfate group, or a phosphate group; amphoteric surfactants such as alkylbetaines, alkylimidazolium betaines, alkylamine oxides, and amino acid sulfates, and nonionic surfactants such as glycerin fatty acid esters, sorbitan fatty acid esters, polyoxyethylene alkylamines, polyoxyethylene alkylamine fatty acid esters, N-hydroxyethyl-N-2-hydroxyalkylamine, and alkyldiethanolamides.
The surfactant may be a reactive emulsifier having a polymerizable group, and a polymer surfactant obtained by increasing the molecular weight of a monomer component containing the surfactant or the reactive emulsifier may be used.
Examples of the conductive polymer include polythiophene, polyaniline, polypyrrole, and a derivative thereof.
The content of the antistatic agent in the adhesive composition is usually 3 parts by mass or less, preferably 0.01 to 3 parts by mass, and more preferably 0.05 to 2.5 parts by mass, based on 100 parts by mass of the polymer.
< organic solvent >
The adhesive composition may not necessarily contain a solvent, but may contain an organic solvent for adjusting the coatability thereof. The content of the organic solvent in the binder composition is usually 30 to 90% by mass, preferably 30 to 85% by mass. In the present specification, "solid content" refers to all components excluding the organic solvent from the components contained in the binder composition, and "solid content concentration" refers to the proportion of the solid content with respect to 100 mass% of the binder composition.
[ adhesive tape ]
The adhesive tape of the present invention includes, for example: a double-sided adhesive sheet having only an adhesive layer formed on a release-treated cover film (hereinafter also referred to as a separator), a double-sided adhesive sheet having a substrate and the adhesive layer formed on both sides of the substrate (in this case, the substrate is also referred to as a core material), a single-sided adhesive sheet having a substrate and the adhesive layer formed on one side of the substrate, and an adhesive sheet having a release-treated cover film adhered to the surface of the adhesive layer of these adhesive sheets not in contact with the substrate.
Examples of the substrate include a polyester film such as polyethylene terephthalate (PET), a plastic film such as a polyolefin film such as polycarbonate, polyethylene, polypropylene, and an ethylene-vinyl acetate copolymer, a woven fabric, and a nonwoven fabric. Further, as the plastic film, woven fabric, or nonwoven fabric, a material blended with various additives, a material obtained by laminating a plurality of layers, or the like can be used. The thickness of the substrate is not particularly limited, but is usually 1 to 2000. mu.m, particularly preferably 3 to 500. mu.m, and particularly preferably 10 to 100. mu.m.
Examples of the cover film include plastic films such as polyester films of polyethylene terephthalate (PET) and the like, and polyolefin films of polycarbonate, polyethylene, polypropylene, ethylene-vinyl acetate copolymer and the like, the surfaces of which are optionally subjected to a peeling treatment. As the plastic film, a plastic film containing various additives, a plastic film obtained by laminating a plurality of layers, or the like can be used.
As a method for applying the pressure-sensitive adhesive composition, a method of applying and drying the pressure-sensitive adhesive composition to a predetermined thickness by a known method, for example, spin coating, doctor blade coating, roll coating, bar coating, blade coating, die coating, or gravure coating can be used, and the pressure-sensitive adhesive layer can be formed.
The thickness of the pressure-sensitive adhesive layer formed by a single application step is 30 μm or more, preferably 40 μm or more, and more preferably 50 μm or more. The pressure-sensitive adhesive layer has a thickness of 30 μm or more formed in a single application step, but a plurality of the pressure-sensitive adhesive layers may be stacked. In particular, when the pressure-sensitive adhesive layer is formed in a plurality of layers, the total thickness of the pressure-sensitive adhesive layer is usually 60 μm or more. The upper limit of the total thickness of the pressure-sensitive adhesive layer is not particularly limited, and is usually 1000 μm or less. When the pressure-sensitive adhesive layer is formed in a plurality of layers, a substrate may be provided between the pressure-sensitive adhesive layers, or a plurality of pressure-sensitive adhesive layers may be directly stacked without providing a substrate.
[ Total VOC concentration ]
Total Volatile Organic Compound (TVOC) concentration of the adhesive tape of the present invention calculated using a test piece having an adhesive layer area of 100mm × 100mm and a 5L sampling bag3The following. In the present specification, a Tedlar (registered trademark) bag (manufactured by GL Science: model: AA-5) was used as a sampling bag.
The present inventors have found that the VOC concentration cannot be achieved by conventional adhesive tapes. Further, as a result of intensive studies, it was found that the contribution of isoparaffin and alcohol has a great influence on the VOC concentration. Furthermore, the present inventors have found that the total VOC concentration can be suppressed to 10000. mu.g/m, while the necessary physical properties can be secured, by adjusting the composition of the polymer, the kind of initiator used in synthesizing the polymer, the amount of the initiator remaining in the pressure-sensitive adhesive composition, and the drying conditions of the pressure-sensitive adhesive layer3The following.
First, as the initiator, it is preferable to use an initiator having an isoparaffin content as small as possible as a diluent. That is, as the initiator, it is preferable to use an initiator whose decomposition temperature is high to the extent that a diluent is not necessary. Specifically, the content of isoparaffin in the initiator is preferably 0.03 mass% or less, more preferably 0.02 mass% or less, and still more preferably 0.01 mass% or less, based on the total solid content of the adhesive composition. In addition, it is particularly preferable that the initiator does not substantially contain isoparaffin. Here, "isoparaffin" refers to chain saturated hydrocarbons having a side chain and having about 20 or more carbon atoms.
Furthermore, the residual amount of the above-mentioned initiator in the adhesive composition is preferably as small as possible. For this reason, for example, it is preferable to reduce the amount of the initiator used, or to use an initiator having a low decomposition temperature, or to increase the polymerization termination temperature.
As the initiator having a relatively high decomposition temperature, for example, PBND100[ day oil preparation; tert-butyl peroxyneodecanoate, V601[ and Wako pure chemical industries; dimethyl 2, 2' -azobis (2-methylpropionate) ], AIBN [ and Wako pure chemical industries; (2, 2 ' -azobis (isobutyronitrile) ], V-65[ Wako pure chemical industries, Ltd., (2, 2 ' -azobis (2, 4-dimethylvaleronitrile) ], V-59[ Wako pure chemical industries, Ltd., (2, 2 ' -azobis (2-methylbutyronitrile) ], PEROYL [ Nichiol preparation; dilauroyl peroxide ], etc., however, these are merely illustrative, and other initiators may of course be used.
In addition, the drying conditions of the adhesive layer also have an effect on the total VOC concentration. By performing the drying of the adhesive layer at a high temperature for a long time, the total VOC concentration can be reduced. When a (meth) acrylic acid-containing polymer is used as in the system of the present invention, the contribution of alcohol in VOC becomes relatively large, and therefore, adjustment of drying conditions becomes particularly important.
Here, the concentration of isoparaffin calculated using the test piece and the sampling bag is preferably 5000. mu.g/m3The concentration is more preferably 4000. mu.g/m3Hereinafter, more preferably 3000. mu.g/m3The following. Further, the alcohol concentration calculated using the test piece and the sampling bag is preferably 3000. mu.g/m3More preferably 2500. mu.g/m3Hereinafter, more preferably 2000. mu.g/m3The following.
< example >
The present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples. In the following description of examples and the like, "part" means "part by mass" unless otherwise specified.
Synthesis of polymers
[ Synthesis examples 1 to 7]
In a reaction apparatus equipped with a stirrer, a reflux condenser, a thermometer, and a nitrogen gas introduction tube, N-Butyl Acrylate (BA), 2-hydroxyethyl acrylate (2HEA), Acrylic Acid (AA), Dimethylaminoethyl Methacrylate (DM), N-isopropylacrylamide (NIPAM), hydroxyethyl acrylate (HEA), and vinyl acetate (VAc) were added in the proportions shown in table 1, 100 parts of ethyl acetate was added, and the temperature was raised to 80 ℃ while introducing nitrogen gas. Then, an initiator was added in the ratio shown in Table 1, and polymerization was carried out at 80 ℃ for 6 hours under a nitrogen atmosphere. After the reaction, the reaction mixture was diluted with ethyl acetate to prepare a polymer solution having a solid content of 50% by mass. PBND100, PBND, PHPV, PBPV and PL355 are initiators produced in solar oil, and V601 is an initiator produced by Wako pure chemical industries.
< Table 1>
The polymers obtained in Synthesis examples 1 to 7 were mixed with a tackifier resin, a crosslinking agent, and the like as needed to obtain an adhesive composition. In the following table 2, the initiator residual amount and the amount of Isoparaffin (IP) in the initiator are shown together with the composition thereof. Here, the IP content and the initiator residual amount in table 2 represent the amount relative to the total solid content of the adhesive composition. In example 5 and reference example 3, PCJ (polymerized rosin ester resin, product of harmima chemical) was used as a tackifier resin.
< Table 2>
Each of the obtained adhesive compositions was applied to a light release film and dried to form an adhesive layer having a thickness of 55 μm. The adhesive layer was transferred to one surface of a PET film (Lumiror, Toray) having a thickness of 25 μm. The above-mentioned step of forming an adhesive layer having a thickness of 55 μm was performed again, and the adhesive layer was transferred to the other side of the former PET film. That is, the pressure-sensitive adhesive tape had a (pressure-sensitive adhesive layer/PET film (substrate)/pressure-sensitive adhesive layer) structure, the total thickness of the pressure-sensitive adhesive layer was 110 μm, and the total thickness of the pressure-sensitive adhesive tape was 135 μm.
[ Total VOC concentration ]
The adhesive tape was cut out in an area of 100 mm. times.100 mm, and the amounts of total VOC, ethyl acetate, toluene, alcohol and Isoparaffin (IP) were measured using a 5L Tedlar bag (manufactured by GL Science: model: AA-5). Here, each detected amount is a value obtained by converting the area of a peak corresponding to each target substance analyzed by a gas chromatograph into toluene. The total VOC is a value obtained by converting the sum of detection peak areas of gas chromatography detected in the range of n-hexane to n-hexadecane into a toluene detection peak area. The isoparaffin concentration is a value obtained by converting the sum of the areas of the detection peak groups corresponding to the paraffin-derived moieties into a toluene detection peak area. These results are shown together in Table 2.
As shown in Table 2, in examples 1 to 5, the total VOC content was suppressed to 10000. mu.g/m3The following. On the other hand, in comparative examples 1 to 4, the total VOC content exceeded 10000. mu.g/m3. Here, for example, comparing example 1 with comparative example 1, it is clear that the total VOC amount can be greatly reduced by increasing the drying temperature from 90 ℃ to 120 ℃ in addition to using the polymer P3. Further, as is clear from comparison of examples 1 to 5 with comparative examples 2 to 4, the total VOC content can be significantly reduced by using an initiator having a small isoparaffin content.
[ adhesive Properties ]
The adhesive properties of example 5 and reference example 3 were also measured. As shown in Table 3 below, L-45 (manufactured by Soken chemical Co., Ltd., toluene diisocyanate) and TD-75 (manufactured by Soken chemical Co., Ltd., trimethylolpropane adduct of toluene diisocyanate) were used as crosslinking agents (curing agents).
< Table 3>
(Retention force)
The holding power was measured according to JIS Z1541 by cutting the pressure-sensitive adhesive sheet into a width of 20mm, sticking the sheet to an SUS plate in a 20 × 20mm area, applying a load of 1Kg under a temperature of 40 ℃ or 80 ℃, standing for 1 hour, and observing the presence or absence of dropping.
(curved surface sticking test)
The obtained adhesive tape was transferred to a polyether polyurethane foam having a thickness of 10mm to prepare a test tape for a curved surface adhesion test. The test tape was cut into 20 mm. times.50 mm pieces to prepare test pieces. The test piece was stuck to a SUS304 cylinder of 50 mm. phi. or 30 mm. phi. which was ground with No. 280 water-resistant grinding paper. The test piece was left standing at 80 ℃ or 23 ℃ for 24 hours, and the floating or peeling distance of the edge portion of the test piece was measured.
(Rolling ball tack test)
Determined by the j.dow method. Specifically, an adhesive tape obtained by peeling a PET release film from a test piece cut to a width of 10cm was attached to an inclined surface inclined at an angle of 30 degrees so that an adhesive layer was exposed. Next, the steel ball is run from above the inclined surface and then slid on the adhesive surface (adhesive layer surface). The run-up distance at this time was 10cm, and the glide distance was 10 cm. The temperature was 23 ℃ or 10 ℃ and the humidity was 50% RH or 10% RH. Then, a sliding test was performed while changing the diameter of the steel ball, and the maximum diameter of the steel ball that stopped sliding in the adhesion surface was determined. The steel balls used had a diameter of X/32 inch (where X is an integer in the range of 1 to 32), and the numerical values shown in Table 3 refer to the value of X.
As shown in table 3, the adhesive tape of example 5 had sufficient adhesive performance. In addition, the adhesive tape of example 5 was more excellent in holding power at 80 ℃ and curved surface adhesiveness at 23 ℃ than the adhesive tape of reference example 3. This difference is considered to be caused by the adhesive tape of example 5 having an adhesive composition containing a copolymer containing acrylic acid as a monomer component.
Claims (5)
1. An adhesive tape comprising an adhesive layer containing an adhesive composition, wherein the adhesive composition contains a polymer obtained by copolymerizing a monomer mixture containing (meth) acrylic acid, the adhesive layer has a thickness of 30 [ mu ] m or more, and the adhesive tape has a Total Volatile Organic Compound (TVOC) concentration of 10000 [ mu ] g/m3In the following, the following description is given,the total volatile organic compound TVOC concentration was calculated using a test piece having an area of 100mm × 100mm of the adhesive layer and a 5L sample bag.
2. The adhesive tape according to claim 1, wherein the alcohol concentration calculated using the test piece and the sampling bag is 3000 μ g/m3The following.
3. The adhesive tape according to claim 1 or 2, wherein the isoparaffin concentration calculated using the test piece and the sampling bag is 5000 μ g/m3The following.
4. The adhesive tape according to any one of claims 1 to 3, wherein the isoparaffin content in the initiator used in the copolymerization is 0.03 mass% or less with respect to the total solid content of the adhesive composition.
5. The adhesive tape according to any one of claims 1 to 4, wherein the initiator used in the copolymerization is substantially free of an isoparaffin.
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| Application Number | Priority Date | Filing Date | Title |
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| JP2018-060916 | 2018-03-27 | ||
| JP2018060916 | 2018-03-27 | ||
| PCT/JP2019/005982 WO2019187787A1 (en) | 2018-03-27 | 2019-02-19 | Adhesive tape |
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| CN111742024A true CN111742024A (en) | 2020-10-02 |
| CN111742024B CN111742024B (en) | 2022-12-23 |
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| JP (1) | JPWO2019187787A1 (en) |
| CN (1) | CN111742024B (en) |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013075980A (en) * | 2011-09-30 | 2013-04-25 | Fujikura Kasei Co Ltd | Adhesive composition, and laminate |
| JP2013213203A (en) * | 2012-03-09 | 2013-10-17 | Nippon Synthetic Chem Ind Co Ltd:The | Acrylic adhesive composition, acrylic adhesive, and adhesive for transparent electrode, touch panel and image display device each using the same |
| JP2016047924A (en) * | 2014-08-27 | 2016-04-07 | 日本合成化学工業株式会社 | Adhesive composition, adhesive and adhesive sheet |
| JP2017057303A (en) * | 2015-09-17 | 2017-03-23 | Dic株式会社 | Adhesive tape, manufacturing method therefor, and electronic device |
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| JP5049426B2 (en) * | 2000-08-31 | 2012-10-17 | 日東電工株式会社 | Acrylic adhesive manufacturing method |
| JP2011153190A (en) * | 2010-01-26 | 2011-08-11 | Nitto Denko Corp | Conductive adhesive tape |
| KR101552741B1 (en) * | 2010-04-05 | 2015-09-11 | (주)엘지하우시스 | Pressure-sensitive adhesive composition for touch panel, pressure-sensitive adhesive film and touch panel |
| JP5834325B2 (en) * | 2011-12-22 | 2015-12-16 | 東洋インキＳｃホールディングス株式会社 | Pressure-sensitive adhesive composition and pressure-sensitive adhesive film using the same |
| JP2013155367A (en) * | 2012-01-04 | 2013-08-15 | Nitto Denko Corp | Adhesive composition |
| JP6241816B2 (en) * | 2013-03-29 | 2017-12-06 | サイデン化学株式会社 | Optical pressure-sensitive adhesive composition and method for producing optical pressure-sensitive adhesive composition |
| JP6390894B2 (en) * | 2014-06-17 | 2018-09-19 | Dic株式会社 | Adhesive tape |
| JP2017014333A (en) * | 2015-06-29 | 2017-01-19 | Dic株式会社 | Adhesive tape, method for producing the same, article and electronic apparatus |
| CN107022313A (en) * | 2016-01-29 | 2017-08-08 | 日东电工株式会社 | Double-sided adhesive sheet and application thereof |
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- 2019-02-19 WO PCT/JP2019/005982 patent/WO2019187787A1/en active Application Filing
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013075980A (en) * | 2011-09-30 | 2013-04-25 | Fujikura Kasei Co Ltd | Adhesive composition, and laminate |
| JP2013213203A (en) * | 2012-03-09 | 2013-10-17 | Nippon Synthetic Chem Ind Co Ltd:The | Acrylic adhesive composition, acrylic adhesive, and adhesive for transparent electrode, touch panel and image display device each using the same |
| JP2016047924A (en) * | 2014-08-27 | 2016-04-07 | 日本合成化学工業株式会社 | Adhesive composition, adhesive and adhesive sheet |
| JP2017057303A (en) * | 2015-09-17 | 2017-03-23 | Dic株式会社 | Adhesive tape, manufacturing method therefor, and electronic device |
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| TW201942287A (en) | 2019-11-01 |
| CN111742024B (en) | 2022-12-23 |
| WO2019187787A1 (en) | 2019-10-03 |
| JPWO2019187787A1 (en) | 2021-02-25 |
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