WO2019187787A1 - Ruban adhésif - Google Patents

Ruban adhésif Download PDF

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Publication number
WO2019187787A1
WO2019187787A1 PCT/JP2019/005982 JP2019005982W WO2019187787A1 WO 2019187787 A1 WO2019187787 A1 WO 2019187787A1 JP 2019005982 W JP2019005982 W JP 2019005982W WO 2019187787 A1 WO2019187787 A1 WO 2019187787A1
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Prior art keywords
meth
pressure
sensitive adhesive
adhesive tape
acrylate
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PCT/JP2019/005982
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English (en)
Japanese (ja)
Inventor
雅代 坂下
真央 山下
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綜研化学株式会社
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Priority to CN201980014238.0A priority Critical patent/CN111742024B/zh
Priority to JP2020510412A priority patent/JPWO2019187787A1/ja
Publication of WO2019187787A1 publication Critical patent/WO2019187787A1/fr

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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
    • 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]

Definitions

  • This disclosure relates to an adhesive tape.
  • VOC volatile organic compounds
  • JP 2008-285554 A Japanese Patent No. 5142446
  • an object of this invention is to provide the adhesive tape which can make the outstanding adhesive performance and reduction of the amount of VOC compatible.
  • a pressure-sensitive adhesive tape comprising a pressure-sensitive adhesive layer containing a pressure-sensitive adhesive composition, wherein the pressure-sensitive adhesive composition contains a polymer obtained by copolymerizing a monomer mixture containing (meth) acrylic acid,
  • the pressure-sensitive adhesive layer has a thickness of 30 ⁇ m or more, and the pressure-sensitive adhesive tape has a total volatile organic compound (TVOC) calculated using a test piece having a surface area of the pressure-sensitive adhesive layer of 100 mm ⁇ 100 mm and a 5 L sampling bag.
  • TVOC total volatile organic compound
  • an adhesive tape capable of achieving both excellent adhesive performance and a reduced VOC amount.
  • polymer is used to include homopolymers and copolymers
  • polymerization is used to include homopolymerization and copolymerization.
  • the compound represented by formula (i) (i is a formula number) is also simply referred to as “compound (i)”.
  • (meth) acryl means acryl or methacryl
  • (meth) acrylate means acrylate or methacrylate
  • (meth) acrylo means acrylo or methacrylo.
  • the adhesive tape which concerns on 1 aspect of this invention is equipped with the adhesive layer containing the adhesive composition.
  • This pressure-sensitive adhesive composition contains a polymer obtained by copolymerizing a monomer mixture.
  • the pressure-sensitive adhesive composition is typically an acrylic pressure-sensitive adhesive composition.
  • 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, but is, for example, 0.5 to 10% by mass, preferably 0.6 to 8% by mass, and more preferably based on the total mass of all raw material monomers. Is 0.7 to 7% by mass, more preferably 0.8 to 6% by mass.
  • the VOC amount (especially alcohol amount) of the adhesive tape mentioned later may become high.
  • the content of (meth) acrylic acid is excessively small, the effect of adding (meth) acrylic acid as a monomer is slightly weakened.
  • This polymer may be synthesized by a normal radical polymerization method or may be synthesized by a living radical polymerization method.
  • the weight average molecular weight (Mw) of this polymer measured by gel permeation chromatography (GPC) method is, for example, 50,000 to 3,000,000, preferably 50,000 to 2,500,000. More preferably, it is 50,000 to 2,000,000.
  • the molecular weight distribution (Mw / Mn) measured by the GPC method of this polymer is, for example, 30.0 or less, preferably 25.0 or less, more preferably 20.0 or less.
  • This polymer is, for example, a (meth) acrylic polymer.
  • This polymer may be a random polymer or a block polymer.
  • This polymer may be, for example, a (meth) acrylic random polymer or a (meth) acrylic block polymer.
  • the type of monomer other than (meth) acrylic acid that can be contained in the monomer mixture is not particularly limited.
  • (meth) acrylic acid ester is mainly used, but other functional group-containing monomers and copolymerizable monomers may be further used.
  • (meth) acrylic acid ester examples include alkyl (meth) acrylates, alkoxyalkyl (meth) acrylates, alkoxypolyalkylene glycol mono (meth) acrylates, alicyclic groups, or aromatic group-containing (meth) acrylates. .
  • functional group-containing (meth) acrylates such as hydroxyl group-containing (meth) acrylate and carboxy group-containing (meth) acrylate are excluded from (meth) acrylic acid esters.
  • the number of carbon atoms of the alkyl group in the alkyl (meth) acrylate is preferably 1-20.
  • the alkyl (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, iso-propyl (meth) acrylate, n-butyl (meth) acrylate, iso-butyl ( (Meth) acrylate, tert-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,
  • alkoxyalkyl (meth) acrylate examples include methoxymethyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxypropyl (meth) acrylate, 3-ethoxypropyl ( And (meth) acrylate, 4-methoxybutyl (meth) acrylate, and 4-ethoxybutyl (meth) acrylate.
  • alkoxypolyalkylene glycol mono (meth) acrylate examples include methoxydiethylene glycol mono (meth) acrylate, methoxydipropylene glycol mono (meth) acrylate, ethoxytriethylene glycol mono (meth) acrylate, ethoxydiethylene glycol mono (meth) acrylate, And methoxytriethylene glycol mono (meth) acrylate.
  • Examples of the alicyclic group or aromatic group-containing (meth) acrylate include cyclohexyl (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, isobornyl (meth) acrylate, and phenoxyethyl (meth) acrylate. It is done.
  • (Meth) acrylic acid ester can be used alone or in combination of two or more.
  • the total amount of (meth) acrylic acid ester used is, for example, 70 to 99.9% by mass, preferably 80 to 99.5% by mass, and more preferably 85 to 98.95% by mass with respect to the total mass of all raw material monomers. %.
  • 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 carboxy group, an acid anhydride group, a phosphoric acid group, and a sulfuric acid group.
  • the nitrogen atom-containing monomer contains a nitrogen atom, for example, in the form of an amino group or an amide bond.
  • hydroxyl group-containing monomer examples include a hydroxyl group-containing (meth) acrylate, and specific examples include 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
  • hydroxyalkyl (meth) acrylates such as 6-hydroxyhexyl (meth) acrylate and 8-hydroxyoctyl (meth) acrylate.
  • the number of carbon atoms in the alkyl group in the hydroxyalkyl (meth) acrylate is usually 2 to 8, preferably 2 to 6.
  • carboxy group-containing monomer examples include ⁇ -carboxyethyl (meth) acrylate, 5-carboxypentyl (meth) acrylate, mono (meth) acryloyloxyethyl ester succinate, and ⁇ -carboxypolycaprolactone mono (meth) acrylate. , Itaconic acid, crotonic acid, fumaric acid and maleic acid.
  • acid anhydride group-containing monomer include maleic anhydride.
  • Examples of the phosphate group-containing monomer include (meth) acrylic monomers having a phosphate group in the side chain, and examples of the sulfate group-containing monomer include (meth) acrylic monomers having a sulfate group in the side chain.
  • nitrogen atom-containing monomer examples include amino group-containing monomers and amide bond-containing monomers.
  • 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 part of a lactam structure.
  • the nitrogen atom of the amino group is preferably modified with an alkyl group.
  • the alkyl group include those having 1 to 6 carbon atoms, specifically, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, sec-butyl group, Examples thereof include an iso-butyl group and a tert-butyl group.
  • the amino group-containing monomer is more preferably an aminoalkyl (meth) acrylic acid ester.
  • the preferable aspect of the amino group in aminoalkyl (meth) acrylic ester it is the same as that of the above.
  • the alkyl group in the aminoalkyl group include those having 1 to 6 carbon atoms, and specific examples include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, and an n-butyl group. , Sec-butyl group, iso-butyl group, and tert-butyl group.
  • the aminoalkyl group include a tert-butylaminoethyl group, a dimethylaminoethyl group, and a diethylaminoethyl group.
  • amino group-containing monomers include tert-butylaminoethyl methacrylate (TBAEMA), dimethylaminoethyl methacrylate (DMAEMA; DM), diethylaminoethyl methacrylate (DEAEMA), and dimethylaminoethyl acrylate. (DMAEA).
  • TAAEMA tert-butylaminoethyl methacrylate
  • DMAEMA dimethylaminoethyl methacrylate
  • DEAEMA diethylaminoethyl methacrylate
  • DMAEA dimethylaminoethyl acrylate
  • the amide bond-containing monomer is preferably a (meth) acrylamide derivative or a lactam having a vinyl group.
  • the (meth) acrylamide derivative is, for example, N-alkyl (meth) acrylamide, N, N-dialkyl (meth) acrylamide, or diacetone acrylamide.
  • alkyl group include those having 1 to 6 carbon atoms, specifically, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, sec-butyl group, Examples thereof include an iso-butyl group and a tert-butyl group.
  • amide bond-containing monomer examples include N, N-dimethylacrylamide (DMAA), N, N-diethylacrylamide (DEAA), N-isopropylacrylamide (NIPAM), diacetone acrylamide (DAAM), N-acryloylmorpholine ( ACMO), N-vinyl-2-pyrrolidone (NVP), N-vinyl-caprolactam (NVC), and N- (2-hydroxyethyl) acrylamide (HEAA).
  • DMAA N-dimethylacrylamide
  • DEAA N-diethylacrylamide
  • NIPAM N-isopropylacrylamide
  • DAAM diacetone acrylamide
  • ACMO N-acryloylmorpholine
  • NVP N-vinyl-2-pyrrolidone
  • NVC N-vinyl-caprolactam
  • HEAA N- (2-hydroxyethyl) acrylamide
  • the functional group-containing monomer can be used alone or in combination of two or more.
  • the total amount of the functional group-containing monomer excluding the (meth) acrylic acid is preferably 0 to 15% by mass, more preferably 0.05 to 10% by mass, based on the total mass of all raw material monomers. is there.
  • the total amount of the hydroxyl group-containing polymer is, for example, 0 to 5% by mass, preferably 0.05 to 2% by mass, and more preferably 0.00%, based on the total mass of all raw material monomers.
  • the content is 1 to 1% by mass, more preferably 0.12 to 0.8% by mass.
  • Copolymerizable monomers examples include styrene, methyl styrene, dimethyl styrene, trimethyl styrene, propyl styrene, butyl styrene, hexyl styrene, heptyl styrene, octyl styrene, and other alkyl styrenes, fluorostyrene, chlorostyrene, bromostyrene, dibromo.
  • styrene monomers such as styrene, iodostyrene, nitrostyrene, acetylstyrene and methoxystyrene, and vinyl acetate.
  • the copolymerizable monomer can be used alone or in combination of two or more.
  • the pressure-sensitive adhesive composition includes, 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, It may further contain nanoparticles and the like.
  • the pressure-sensitive adhesive composition may contain a tackifier resin.
  • a tackifying resin in addition to the above-mentioned polymer as a component constituting the pressure-sensitive adhesive composition, for example, it is generally difficult to adhere to an acrylic pressure-sensitive adhesive, such as polyethylene, polypropylene, and other olefinic adherends. Even for this, good adhesion (tackiness) can be exhibited. Moreover, the constant load peeling resistance of the obtained adhesive layer can be improved.
  • a rosin ester resin is preferably used, and a polymerized rosin ester resin may be used in combination.
  • a terpene tackifier resin or a hydrocarbon petroleum resin may be used.
  • the tackifier resin may be used alone or in combination of two or more.
  • the total content of the tackifying resin in the pressure-sensitive 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 with respect to 100 parts by mass of the polymer.
  • Crosslinking agent examples include isocyanate compounds, epoxy compounds, metal chelate compounds, and the like.
  • an isocyanate compound having two or more isocyanate groups in one molecule is usually used.
  • the isocyanate compound include aliphatic diisocyanate, alicyclic diisocyanate, and aromatic diisocyanate.
  • Aliphatic diisocyanates include ethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, 2-methyl-1,5-pentane diisocyanate, 3-methyl-1,5-pentane diisocyanate, 2,2,4-trimethyl
  • aliphatic diisocyanates having 4 to 30 carbon atoms such as -1,6-hexamethylene diisocyanate.
  • alicyclic diisocyanate examples include 7 to 30 carbon atoms such as isophorone diisocyanate, cyclopentyl diisocyanate, cyclohexyl diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated diphenylmethane diisocyanate, and hydrogenated tetramethylxylene diisocyanate.
  • Diisocyanate is mentioned.
  • aromatic diisocyanate examples include aromatic diisocyanates having 8 to 30 carbon atoms such as phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, naphthylene diisocyanate, diphenyl ether diisocyanate, diphenylmethane diisocyanate, and diphenylpropane diisocyanate.
  • isocyanate compound having 3 or more isocyanate groups in one molecule examples include aromatic polyisocyanate, aliphatic polyisocyanate, and alicyclic polyisocyanate. Specific examples include 2,4,6-triisocyanate toluene, 1,3,5-triisocyanate benzene, and 4,4 ′, 4 ′′ -triphenylmethane triisocyanate.
  • Diphenylmethane diisocyanate trimer polymethylene polyphenyl polyisocyanate, hexamethylene diisocyanate or tolylene diisocyanate biuret or isocyanurate, reaction product of trimethylolpropane with tolylene diisocyanate or xylylene diisocyanate (eg tolylene diisocyanate) Isocyanate or xylylene diisocyanate trimolecular adducts), trimethylolpropane and hexamethylene diisocyanate reaction products (eg hexamethylene diisocyanate) Over 3 molecular adduct g), polyether polyisocyanates, and polyester polyisocyanates.
  • an epoxy compound having 2 or more epoxy groups in one molecule is usually used.
  • metal chelate compound for example, alkoxide, acetylacetone, ethyl acetoacetate and the like are coordinated to a polyvalent metal such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium, zirconium, etc.
  • a polyvalent metal such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium, zirconium, etc.
  • Compounds. Specific examples include aluminum isopropylate, aluminum secondary butyrate, aluminum ethyl acetoacetate / diisopropylate, aluminum trisethyl acetoacetate, and aluminum trisacetylacetonate.
  • the crosslinking agent is in the range of 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 with respect to 100 parts by mass in total with the polymer. When a crosslinking agent is included in this range, it is possible to balance the various required adhesive properties.
  • the silane coupling agent can firmly adhere the pressure-sensitive adhesive layer to an adherend such as a glass substrate, and can prevent the pressure-sensitive adhesive layer from peeling off in a high-humidity heat environment.
  • silane coupling agent examples include polymerizable unsaturated group-containing silane coupling agents such as vinyltrimethoxysilane, vinyltriethoxysilane, and methacryloxypropyltrimethoxysilane; 3-glycidoxypropyltrimethoxysilane, 3- Epoxy group-containing silane cups such as glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane Ring agent; amino group-containing silane such as 3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane Coupling agent Halogen-containing si
  • an epoxy group-containing silane coupling agent is preferable in terms of stress relaxation.
  • the content of the silane coupling agent is usually 1 part by mass or less, preferably 0.01-1 part by mass, more preferably 0.05-0. 5 parts by mass. When the content is in the above range, peeling of the pressure-sensitive adhesive layer in a high-humidity heat environment and bleeding of the silane coupling agent in a high-temperature environment tend to be prevented.
  • Antistatic agent examples include a surfactant, an ionic compound, and a conductive polymer.
  • surfactant examples include cationic surfactants having cationic groups such as quaternary ammonium salts, amide quaternary ammonium salts, pyridium salts, primary to tertiary amino groups; sulfonate groups, sulfate esters Anionic surfactants having an anionic group such as a base or a phosphate ester base; amphoteric surfactants such as alkylbetaines, alkylimidazolinium betaines, alkylamine oxides, amino acid sulfates, glycerin fatty acid esters
  • Nonionic surfactants such as sorbitan fatty acid esters, polyoxyethylene alkylamines, polyoxyethylene alkylamine fatty acid esters, N-hydroxyethyl-N-2-hydroxyalkylamines and alkyldiethanolamides It is done.
  • a reactive emulsifier having a polymerizable group is also exemplified as the surfactant, and a polymer surfactant obtained by increasing the molecular weight of the monomer component containing the above surfactant or reactive emulsifier can also be used.
  • Examples of the conductive polymer include polythiophene, polyaniline, polypyrrole, and derivatives thereof.
  • the content of the antistatic agent is usually 3 parts by mass or less, preferably 0.01 to 3 parts by mass, more preferably 0.05 to 2.5 parts by mass with respect to 100 parts by mass of the polymer. Part by mass.
  • the pressure-sensitive adhesive composition does not necessarily contain a solvent, but may contain an organic solvent in order to adjust its coatability.
  • the content of the organic solvent is usually 30 to 90% by mass, preferably 30 to 85% by mass.
  • solid content refers to all components excluding the organic solvent among the components contained in the pressure-sensitive adhesive composition
  • solid content concentration refers to 100% by mass of the pressure-sensitive adhesive composition. The ratio of the said solid content is said.
  • the pressure-sensitive adhesive tape according to the present invention is formed on, for example, a double-sided pressure-sensitive adhesive sheet having only an adhesive layer formed on a peeled cover film (hereinafter also referred to as a separator), a base material, and both surfaces of the base material.
  • Double-sided pressure-sensitive adhesive sheet having the pressure-sensitive adhesive layer in this case, the base material is also referred to as a core material
  • a base material in this case, the base material is also referred to as a core material
  • a base material is also referred to as a core material
  • a base material includes a pressure-sensitive adhesive sheet in which a peeled cover film is attached to a surface of the pressure-sensitive adhesive layer that is not in contact with the base material.
  • the base material examples include polyester films such as polyethylene terephthalate (PET), plastic films such as polycarbonate, polyethylene, polypropylene, polyolefin films such as ethylene-vinyl acetate copolymer, woven fabrics and non-woven fabrics.
  • PET polyethylene terephthalate
  • plastic films such as polycarbonate, polyethylene, polypropylene, polyolefin films such as ethylene-vinyl acetate copolymer, woven fabrics and non-woven fabrics.
  • the thickness of the substrate is not particularly limited, but is usually 1 to 2000 ⁇ m, particularly 3 to 500 ⁇ m, especially 10 to 100 ⁇ m.
  • cover film examples include a plastic film such as a polyester film such as polyethylene terephthalate (PET) optionally having a surface-exfoliated treatment, a polyolefin film such as polycarbonate, polyethylene, polypropylene, and ethylene-vinyl acetate copolymer.
  • PET polyethylene terephthalate
  • polyolefin film such as polycarbonate, polyethylene, polypropylene, and ethylene-vinyl acetate copolymer.
  • the plastic film one in which various additives are blended or one in which a plurality of layers are laminated can be used.
  • a known thickness such as a spin coating method, a knife coating method, a roll coating method, a bar coating method, a blade coating method, a die coating method, or a gravure coating method may be used.
  • the method of applying and drying can be used, and the pressure-sensitive adhesive layer can be formed in this way.
  • the pressure-sensitive adhesive layer has a thickness formed by a single coating step of 30 ⁇ m or more, preferably 40 ⁇ m or more, and more preferably 50 ⁇ m or more.
  • the said adhesive layer is 30 micrometers or more in thickness formed by the single application
  • the total thickness of the pressure-sensitive adhesive layer is usually 60 ⁇ m or more.
  • the upper limit of the total thickness of the said adhesive layer is not specifically limited, Usually, it is 1000 micrometers or less.
  • the pressure-sensitive adhesive tape according to the present invention has a total volatile organic compound (TVOC) concentration of 10,000 ⁇ g / m 3 or less calculated using a test piece having an area of the pressure-sensitive adhesive layer of 100 mm ⁇ 100 mm and a 5 L sampling bag. .
  • a Tedlar (registered trademark) bag manufactured by GL Sciences: model: AA-5) is used as the sampling bag.
  • the present inventors have found that the above-mentioned VOC concentration cannot be achieved with a conventional adhesive tape. And as a result of earnest examination, it discovered that the contribution of isoparaffin and alcohol had big influence on the said VOC density
  • the initiator it is preferable to use one having as little isoparaffin content as a diluent. That is, it is preferable to use an initiator having a decomposition temperature that is so high that a diluent is unnecessary.
  • the isoparaffin content in the initiator is preferably 0.03% by mass or less, more preferably 0.02% by mass or less, based on the total solid content of the pressure-sensitive adhesive composition. More preferably, the content is 0.01% by mass or less.
  • the initiator does not substantially contain isoparaffin.
  • the “isoparaffin” means a chain saturated hydrocarbon having a side chain and having about 20 or more carbon atoms.
  • the remaining amount of the initiator in the pressure-sensitive adhesive composition is preferably as small as possible.
  • Examples of the initiator having a relatively high decomposition temperature include PBND100 [manufactured by NOF; t-butylperoxynedecanoate], V601 [manufactured by Wako Pure Chemical Industries; (2,2′-Azobis (isobutyronitrile)), V-65 [Wako Pure Chemical Industries; (2,2′-Azobis (2,4-dimethylhydrerontrile)], V-59 [Wako Pure Chemicals] (2,2′-Azobis (2-methylbutyronitrile)), and Parroyl L [manufactured by NOF; DialoylPeroxide] can be used, but these are merely examples, and other It is of course also possible to use the initiator.
  • the drying condition of the pressure-sensitive adhesive layer affects the total VOC concentration.
  • the total VOC concentration can be reduced.
  • the contribution of alcohol in the VOC becomes relatively large, so that adjustment of drying conditions is particularly important.
  • isoparaffin concentration calculated using the test piece and the sampling bag is preferably 5000 [mu] g / m 3 or less, more preferably 4000 ⁇ g / m 3 or less, is 3000 ⁇ g / m 3 or less More preferably. Further it, the alcohol concentration calculated using the test piece and the sampling bag is preferably at 3000 ⁇ g / m 3 or less, more preferably 2500 g / m 3 or less, 2000 [mu] g / m 3 or less Is more preferable. ⁇ Example>
  • an initiator was added at a rate described in Table 1, and a polymerization reaction was performed at 80 ° C. for 6 hours in a nitrogen gas atmosphere. After completion of the reaction, it was diluted with ethyl acetate to prepare a polymer solution having a solid content concentration of 50% by mass.
  • PBND100, PBND, PHPV, PBPV, and PL355 are NOF initiators, and V601 is an initiator manufactured by Wako Pure Chemical Industries.
  • the polymers obtained in Synthesis Examples 1 to 7 were mixed with a tackifying resin and a crosslinking agent as necessary to obtain a pressure-sensitive adhesive composition.
  • Table 2 shows the remaining amount of initiator and the amount of isoparaffin (IP) in the initiator together with the composition.
  • IP isoparaffin
  • the IP content and the remaining amount of initiator in Table 2 represent amounts relative to the total solid content of the pressure-sensitive adhesive composition.
  • PCJ polymerized rosin ester resin, manufactured by Harima Chemicals
  • Each obtained pressure-sensitive adhesive composition was coated on a light release film and dried to form a pressure-sensitive adhesive layer having a thickness of 55 ⁇ m.
  • the pressure-sensitive adhesive layer was transferred to one surface of a PET film having a thickness of 25 ⁇ m (Lumirror: manufactured by Toray).
  • the procedure for forming the 55 ⁇ m thick pressure-sensitive adhesive layer was performed again, and the pressure-sensitive adhesive layer was transferred to the other side of the previous PET film. That is, the pressure-sensitive adhesive tape has a structure of (pressure-sensitive adhesive layer / PET film (base material) / pressure-sensitive adhesive layer), and the total thickness of the pressure-sensitive adhesive layer is 110 ⁇ m, and the total thickness of the adhesive tape is 135 ⁇ m.
  • Total VOC concentration The above adhesive tape is cut out in an area of 100 mm ⁇ 100 mm, using a 5 L Tedlar (registered trademark) bag (manufactured by GL Sciences: model: AA-5), with total VOC, ethyl acetate, toluene, alcohol, and isoparaffin (IP ) was measured.
  • each detected amount is a value obtained by converting a peak area corresponding to each target substance analyzed in the gas chromatograph into toluene.
  • the total VOC is a value obtained by converting the sum of the detection peak areas of the gas chromatograph detected in the range from n-hexane to n-hexadecane into a toluene detection peak area.
  • the isoparaffin concentration is a value obtained by converting the total area of detection peak groups corresponding to paraffin-derived parts into a toluene detection peak area. The results are also shown in Table 2.
  • Example 1 the total VOC amount could be suppressed to 10000 ⁇ g / m 3 or less.
  • Comparative Examples 1 to 4 the total VOC amount exceeded 10000 ⁇ g / m 3 .
  • Example 1 and Comparative Example 1 were compared, it was found that the total VOC amount could be greatly reduced by using the polymer P3 and increasing the drying temperature from 90 ° C. to 120 ° C. I understand.
  • Examples 1 to 5 and Comparative Examples 2 to 4 are compared, it can be seen that the total VOC amount can be greatly reduced even by using an initiator having a low isoparaffin content.
  • Holding force is measured in accordance with JISZ1541, the adhesive sheet is cut to 20mm width, pasted so that the area of 20x20mm is in contact with the SUS plate, and a load of 1Kg is applied at a temperature of 40 ° C or 80 ° C. The presence or absence of the fall when left for 1 hour was observed.
  • the obtained adhesive tape was transferred to a 10 mm-thick polyether urethane foam material to obtain a test tape for a curved surface sticking test.
  • This test tape was cut into 20 mm ⁇ 50 mm to obtain a test piece.
  • This test piece was attached to a 50 mm ⁇ or 30 mm ⁇ SUS304 cylinder polished with No. 280 water-resistant abrasive paper. The sample was allowed to stand at 80 ° C. or 23 ° C. for 24 hours, and the test piece edge portion or the peeling distance was measured.
  • the adhesive tape of Example 5 had sufficient adhesive performance.
  • the pressure-sensitive adhesive tape of Example 5 was more excellent in holding power at 80 ° C. and curved surface stickiness at 23 ° C. than the pressure-sensitive adhesive tape of Reference Example 3. This difference is considered to be due to the fact that the pressure-sensitive adhesive tape of Example 5 includes a pressure-sensitive adhesive composition containing a copolymer having acrylic acid as a monomer component.

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  • Adhesive Tapes (AREA)

Abstract

La présente invention concerne un ruban adhésif capable de présenter à la fois une bonne adhérence et une quantité réduite de COV. Ce ruban adhésif est pourvu d'une couche adhésive comportant une composition adhésive. La composition adhésive comprend un polymère obtenu par une polymérisation à degré élevé d'un mélange de monomères contenant un acide (méth)acrylique. L'épaisseur de la première couche adhésive est supérieure ou égale à 30 μm. Dans ce ruban adhésif, la couche adhésive comporte une concentration totale de composés organiques volatils (TVOC) inférieure ou égale à 10000 μg/m3, calculée à l'aide d'un échantillon présentant une surface de couche adhésive de 100 mm X 100 mm et d'un sac d'échantillonnage de 5L.
PCT/JP2019/005982 2018-03-27 2019-02-19 Ruban adhésif WO2019187787A1 (fr)

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JP2020510412A JPWO2019187787A1 (ja) 2018-03-27 2019-02-19 粘着テープ

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WO2011093214A1 (fr) * 2010-01-26 2011-08-04 日東電工株式会社 Ruban adhésif conducteur
JP2013523940A (ja) * 2010-04-05 2013-06-17 エルジー・ハウシス・リミテッド タッチパネル用粘着剤組成物、粘着フィルム及びタッチパネル
JP2013155367A (ja) * 2012-01-04 2013-08-15 Nitto Denko Corp 粘着剤組成物

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JP5807492B2 (ja) * 2011-09-30 2015-11-10 藤倉化成株式会社 粘着剤組成物、および積層体
JP5834325B2 (ja) * 2011-12-22 2015-12-16 東洋インキＳｃホールディングス株式会社 感圧式接着剤組成物、及びそれを用いてなる感圧式接着剤フィルム
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CN111742024A (zh) 2020-10-02
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CN111742024B (zh) 2022-12-23

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