WO2009084511A1 - Composition pour former un film de revêtement pour liaison par contact, de type durcissable par rayonnement d'énergie actinique et papier revêtu d'un adhésif décollable l'utilisant - Google Patents

Composition pour former un film de revêtement pour liaison par contact, de type durcissable par rayonnement d'énergie actinique et papier revêtu d'un adhésif décollable l'utilisant Download PDF

Info

Publication number
WO2009084511A1
WO2009084511A1 PCT/JP2008/073332 JP2008073332W WO2009084511A1 WO 2009084511 A1 WO2009084511 A1 WO 2009084511A1 JP 2008073332 W JP2008073332 W JP 2008073332W WO 2009084511 A1 WO2009084511 A1 WO 2009084511A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
acrylate
active energy
energy ray
composition
Prior art date
Application number
PCT/JP2008/073332
Other languages
English (en)
Japanese (ja)
Inventor
Kousou Kanda
Toshitaka Okabe
Original Assignee
The Nippon Synthetic Chemical Industry Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Nippon Synthetic Chemical Industry Co., Ltd. filed Critical The Nippon Synthetic Chemical Industry Co., Ltd.
Priority to KR1020107007582A priority Critical patent/KR101530400B1/ko
Priority to CN200880115150XA priority patent/CN101855310B/zh
Publication of WO2009084511A1 publication Critical patent/WO2009084511A1/fr

Links

Classifications

    • 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
    • C09J133/04—Homopolymers or copolymers of esters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
    • B05D5/005—Repairing damaged coatings
    • 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
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • 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
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • 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
    • 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
    • C09J7/40—Adhesives in the form of films or foils characterised by release liners
    • C09J7/401—Adhesives in the form of films or foils characterised by release liners characterised by the release coating composition
    • 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
    • C09J7/40—Adhesives in the form of films or foils characterised by release liners
    • C09J7/405—Adhesives in the form of films or foils characterised by release liners characterised by the substrate of the release liner
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking
    • C08L2312/06—Crosslinking by radiation
    • 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
    • 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
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation

Definitions

  • the present invention relates to a composition for forming a pressure-bonded coating film that enables releasable adhesion by pressure bonding, and is a composition for forming an active energy ray-curable pressure-bonded coating film that is cured by active energy rays, and a releasable adhesion using the same It relates to processed paper.
  • Patent Documents 1 and 2 In order to improve the glossiness and working efficiency of the surface, at least selected from a (meth) acrylic copolymer having a specific molecular weight and glass transition temperature, and an ultraviolet curable monomer and oligomer having a (meth) acryloyl group It has been proposed to use an adhesive composition containing a kind of ultraviolet curable component and a photopolymerization initiator (Patent Documents 1 and 2).
  • an adhesive composition containing a (meth) acryloyl group-containing elastic body having a specific molecular weight, an ultraviolet curable component, and a photopolymerization initiator and having the above three components set to a specific content ratio is used. It is also considered to do (Patent Document 3). JP-A-11-349854 JP 2000-136320 A JP 2004-210879 A
  • the adhesive compositions as described in Patent Documents 1 and 2 are in a state in which the composition components are compatible with each other and are uniformly dispersed and have excellent coating stability, but have a problem in curability and are slightly bent when folded. May occur. Moreover, the problem that the adhesive force becomes too strong with the passage of time also arises. On the other hand, the adhesive composition of Patent Document 3 solves such a problem of curability and is excellent in curability and has little change in adhesive strength over time. The stable adhesiveness was not obtained.
  • the market demands an adhesive composition that is excellent in surface gloss of the printing surface, processing work efficiency, and processed paper manufacturing cost performance.
  • An object of the present invention is to provide a composition for forming an active energy ray-curable pressure-sensitive adhesive coating film that has excellent adhesive strength after curing and excellent releasability at the time of peeling, and a releasable adhesive-processed paper using the same.
  • the present invention provides an active energy ray-curable pressure-bonding comprising a carboxyl group-containing acrylic polymer (A), an active energy ray-curable component (B), and a photopolymerization initiator (C).
  • the composition for forming a die-bonded coating film is a first gist.
  • the second gist is a peelable adhesive-treated paper in which the composition for forming an active energy ray-curable pressure-sensitive adhesive coating film is coated on a paper surface and cured with an active energy ray.
  • the photopolymerization initiator is increased too much, the cured product has a low molecular weight, and therefore there is a tendency to suppress the content. It has been found that by containing a carboxyl group, an excellent adhesive composition for peelable adhesive processed paper can be obtained.
  • a folded sheet-like postcard used in the postcard system has a fine silica gel particle that adheres to the paper surface by pressing, so that the paper surfaces stick to each other. Since they do not mesh with each other, they do not stick again.
  • a finer sea-island structure is created on the surface after curing, and by acting as the silica gel, good press adhesion (after peeling) It is considered that it exhibits re-adhesion prevention property.
  • carboxyl groups in the acrylic polymer, the distance between the carboxyl groups is reduced by pressing, and the adhesive force is increased by becoming a distance that allows interaction (hydrogen bonding).
  • carboxyl groups are sterically hindered. Therefore, it is considered that the adhesive force can be prevented from increasing to such an extent that peeling becomes difficult.
  • this invention contains a carboxyl group-containing acrylic polymer (A), an active energy ray-curable component (B), a photopolymerization initiator (C), and contains the photopolymerization initiator (C).
  • An active energy ray-curable pressure-sensitive adhesive film-forming composition having an amount of 10 to 30 parts relative to 100 parts by weight (hereinafter referred to as “parts”) of the active energy ray-curable component (B). Therefore, it eliminates the need for good coating and drying steps during coating, improves the efficiency of processing operations, and enables good curing, with excellent surface gloss and adhesion after curing. When peeled, it has good peelability. Therefore, the peelable adhesive processed paper using this has such excellent adhesive force and peelability, and is highly practical.
  • the coatability is further improved.
  • the resulting adhesive layer has excellent flexibility.
  • the adhesive strength is further improved.
  • the peelable adhesive force is further improved.
  • (B1) At least one of epoxy (meth) acrylate and urethane (meth) acrylate.
  • B2 An ethylenically unsaturated compound other than (b1) having two or more ethylenically unsaturated groups.
  • (B3) An ethylenically unsaturated compound other than (b1) having one ethylenically unsaturated group.
  • the content ratio of (b1) to (b3) is 5 to 20% by weight of (b1), 40 to 80% by weight of (b2), and (b3) with respect to the entire active energy ray-curable component (B). When it is 10 to 40% by weight, the balance between the adhesive force and the peelability can be further improved.
  • composition for forming an active energy ray-curable pressure-sensitive adhesive coating film of the present invention is a carboxyl group-containing acrylic polymer (A), active energy ray-curing property.
  • a composition for forming a pressure-bonded coating film comprising a component (B) and a photopolymerization initiator (C), and active energy such as ultraviolet rays, infrared rays, electromagnetic waves such as X-rays and ⁇ rays, and electron beams Curing with wire.
  • active energy such as ultraviolet rays, infrared rays, electromagnetic waves such as X-rays and ⁇ rays, and electron beams Curing with wire.
  • Carboxyl group-containing acrylic polymer (A) is obtained by copolymerizing a (meth) acrylic acid alkyl ester (a1) and a carboxyl group-containing monomer (a2).
  • the copolymerizable monomer (a3) may be copolymerized.
  • (meth) acrylic acid is acrylic acid or methacrylic acid
  • (meth) acryl is acrylic or methacrylic
  • (meth) acryloyl is acryloyl or methacryloyl
  • (meth) acrylate is acrylate or Each means methacrylate.
  • Examples of the (meth) acrylic acid alkyl ester (a1) include nonyl (meth) acrylate, n-octyl (meth) acrylate, iso-octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-butyl ( And (meth) acrylate, iso-butyl (meth) acrylate, tert-butyl (meth) acrylate, n-propyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, and the like.
  • (meth) acrylic acid alkyl esters having 1 to 10 carbon atoms in the alkyl group are preferably used, and (meth) acrylic acid alkyl esters having 1 to 5 carbon atoms in the alkyl group are particularly preferably used.
  • ethyl (meth) acrylate and n-butyl (meth) acrylate are particularly preferably used.
  • One or more of these (meth) acrylic acid alkyl esters (a1) are used.
  • carboxyl group-containing monomer (a2) examples include (meth) acrylic acid, crotonic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid, acrylamide-N-glycolic acid, cinnamic acid, and (meth) acrylic.
  • Michael adducts of acids eg, acrylic acid dimer, methacrylic acid dimer, acrylic acid trimer, methacrylic acid trimer, acrylic acid tetramer, methacrylic acid tetramer, etc.
  • 2- (meth) acryloyloxyethyl dicarboxylic acid monoester eg, 2 -Acrylyloxyethyl succinic acid monoester, 2-methacryloyloxyethyl succinic acid monoester, 2-acryloyloxyethyl phthalic acid monoester, 2-methacryloyloxyethyl phthalic acid monoester, 2-acryloyloxyethyl Kisa hexahydrophthalic acid monoester, 2-methacryloyloxyethyl hexahydrophthalic acid mono ester) carboxyl group-containing unsaturated monomers such as, and the like.
  • (meth) acrylic acid is used. 1 type, or 2 or
  • Examples of the other copolymerizable monomer (a3) used as necessary include 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 3-chloro-2-hydroxypropyl acrylate, 2-hydroxyethyl.
  • the carboxyl group-containing acrylic polymer (A) used in the present invention is the above-mentioned (meth) acrylic acid alkyl ester (a1), the carboxyl group-containing monomer (a2), and other copolymers as required. It can be obtained by copolymerizing the functional monomer (a3).
  • the (meth) acrylic acid ester monomer (a1) is 75 to 95% by weight, particularly 80 to 93% by weight, more preferably 85 to 90%, based on the entire copolymer component. It is preferable to contain 1% by weight, particularly 1.5 to 8% by weight, more preferably 2 to 6% by weight of the carboxyl group-containing monomer (a2).
  • (A3) is preferably contained in an amount of 5 to 15% by weight, particularly 6 to 14% by weight, more preferably 7 to 13% by weight.
  • the carboxyl group-containing acrylic polymer (A) thus obtained preferably has a weight average molecular weight (Mw) of 100,000 or less, particularly 80,000 or less, more preferably 60,000 or less. . This is because if the weight average molecular weight (Mw) of the carboxyl group-containing acrylic polymer (A) is too large, the resin viscosity increases and the coating property tends to deteriorate.
  • the lower limit of the weight average molecular weight (Mw) of the carboxyl group-containing acrylic polymer (A) is preferably 10,000 or more, particularly 20,000 or more, and more preferably 30,000 or more. This is because if the weight average molecular weight (Mw) of the carboxyl group-containing acrylic polymer (A) is too small, the cohesive force of the adhesive obtained by irradiation with active energy rays is insufficient and the adhesiveness tends to be lowered.
  • the carboxyl group-containing acrylic polymer (A) can be produced by methods well known to those skilled in the art, such as solution radical polymerization, suspension polymerization, bulk polymerization, and emulsion polymerization. Among them, suspension polymerization is preferably used as a method for producing a carboxyl group-containing acrylic polymer (A) satisfying the above conditions because a polymer having a high degree of polymerization can be obtained and the resulting polymer can be easily isolated. . That is, the carboxyl group-containing acrylic polymer (A) is preferably a dry resin obtained by suspension polymerization.
  • a polymerization initiator such as azobisisobutyronitrile can be added as necessary.
  • the glass transition temperature (Tg) of the carboxyl group-containing acrylic polymer (A) is preferably ⁇ 60 to 20 ° C. or less, particularly ⁇ 60 to 0 ° C., more preferably ⁇ 55 to ⁇ It is preferable that it is 10 degrees C or less. This is because if the glass transition temperature (Tg) of the acrylic polymer (A) is too low, the cohesive force tends to be inferior, and conversely if too high, the adhesive tends to become brittle.
  • the weight average molecular weight is a weight average molecular weight in terms of standard polystyrene molecular weight, and is a high performance liquid chromatography (manufactured by Waters, Japan, “Waters 2695 (main body)” and “Waters 2414 (detector)”).
  • the glass transition temperature is calculated from the Fox equation.
  • the content of the carboxyl group-containing acrylic polymer (A) is preferably 5 to 45 parts, more preferably 7 to 35 parts, and more preferably 100 parts by weight of the active energy ray-curable component (B) described later. It is preferably 10 to 25 parts. If the content of the carboxyl group-containing acrylic polymer (A) is too small, sufficient adhesiveness tends to be not obtained. Conversely, if the content is too large, the resulting composition for forming a pressure-bonded coating film of the present invention is sticky. This is because there is a tendency that the feeling becomes stronger, the glossiness is lowered, the adhesiveness is too strong at the time of peeling, and the paper breaks or the blocking resistance of the coated paper is insufficient.
  • the active energy ray-curable component (B) is a component in which a curing reaction occurs due to active energy rays, and at least one of epoxy (meth) acrylate and urethane (meth) acrylate (b1), two or more ethylenically unsaturated groups.
  • the ethylenically unsaturated compound (b2) other than (b1) having [b1] (hereinafter sometimes abbreviated as “polyfunctional compound (b2)”) and the ethylenically unsaturated compound other than (b1) having one ethylenically unsaturated group It is preferably at least one active energy ray-curable component selected from the group consisting of a saturated compound (b3) [hereinafter sometimes abbreviated as “monofunctional compound (b3)”].
  • a saturated compound (b3) hereinafter sometimes abbreviated as “monofunctional compound (b3)”
  • the polyfunctional compound (b2) and the monofunctional compound (b3) ) are preferably used in combination of two or more in terms of promoting the curing reaction. Moreover, it is more preferable that the content of the polyfunctional compound (b2) is larger than the content of the monofunctional compound (b3) because sufficient resin cohesion can be obtained.
  • the components (b1) to (b3) will be described.
  • epoxy (meth) acrylate can be cured at high speed even when the amount of ultraviolet rays is low, and when blended with epoxy (meth) acrylate, the mechanical properties of the product are excellent in fatigue resistance such as bending and impact during postcard products. This is because it tends to be excellent. That is, epoxy (meth) acrylate is excellent in fast curability and adhesive film toughness.
  • the urethane (meth) acrylate has a flexible molecular skeleton, so it can give the product properties such as flexibility and high elasticity, and has a large tensile elongation as a mechanical property, such as bending and impact during postcard products. It is because it tends to be excellent in fatigue resistance.
  • epoxy (meth) acrylate or urethane (meth) acrylate alone or in combination of two types of epoxy (meth) acrylate and urethane (meth) acrylate. It is preferred to use (meth) acrylate alone.
  • Examples of the epoxy (meth) acrylate include diglycidyl ether di (meth) acrylate of bisphenol A, a reaction product of a polyfunctional epoxy compound, (meth) acrylic acid and methyltetrahydrophthalic anhydride, and a polyfunctional epoxy compound. And a reaction product of (meth) acrylic acid, glycerin polyglycidyl ether poly (meth) acrylate, and the like.
  • a viscosity of 100 to 1,000,000 mPa ⁇ s / 25 ° C. is preferable, and 1,000 to 100,000 mPa ⁇ s / 25 ° C. is more preferable from the viewpoint of mechanical properties.
  • urethane (meth) acrylate for example, a urethane (meth) acrylate having a (meth) acryloyl group at both ends connected to a polyoxyalkylene segment or a saturated polyester segment via a urethane bond, or the like.
  • a viscosity of 100 to 100,000 mPa ⁇ s / 60 ° C. is preferable, and 1,000 to 10,000 mPa ⁇ s / 60 ° C. is more preferable from the viewpoint of mechanical properties.
  • the viscosity means a viscosity measured using a B-type viscometer (product name: B-type viscometer; manufactured by Tokyo Keiki Co., Ltd.) under specific temperature conditions (for example, 25 ° C., 60 ° C., etc.).
  • the ethylenically unsaturated compound [polyfunctional compound (b2)] other than (b1) having two ethylenically unsaturated groups is an active energy ray-curable component (used in the composition for forming a pressure-sensitive adhesive coating film of the present invention ( It is used as a copolymerizable compound constituting B) and is a polyfunctional compound having two or more ethylenically unsaturated groups.
  • polyfunctional compound (b2) used in the present invention examples include polyfunctional (meth) acrylate monomers. Specifically, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polytetramethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (Meth) acrylate, dipropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide modified bisphenol A type di (meth) acrylate , Propylene oxide modified bisphenol A di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, glycerin di (meth) Bifunctional (meth) acrylic compounds such as acryl
  • 1,6-hexanediol di (meth) acrylate and trimethylolpropane tri (meth) acrylate are preferably used. These are used singly or in combination of two or more, particularly preferably in combination of two or more.
  • the ethylenically unsaturated compound (b3) [monofunctional compound (b3)] other than (b1) having one ethylenically unsaturated group is an active energy ray curing used in the composition for forming a pressure-sensitive adhesive coating film of the present invention.
  • the monofunctional compound having one ethylenically unsaturated group is used as a copolymerizable compound constituting the functional component (B).
  • Examples of the monofunctional compound (b3) include (meth) acrylic acid alkyl ester ( ⁇ -1) and other monofunctional compounds ( ⁇ -2). Use as a monomer mixture obtained by mixing them is effective. This is preferable.
  • Examples of the (meth) acrylic acid alkyl ester ( ⁇ -1) include (meth) acrylic acid alkyl esters in which the alkyl group has 1 to 20, preferably 2 to 18, and more preferably 4 to 10 carbon atoms. It is done. Specifically, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, n-butyl (meth) acrylate, iso-butyl (meth) acrylate, tert-butyl (meth) acrylate, n -Octyl (meth) acrylate, iso-octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, n-decyl (meth) acrylate, iso-decyl (meth) acrylate, etc.
  • n-octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, and n-butyl (meth) acrylate are preferably used in terms of effects.
  • These (meth) acrylic acid alkyl esters ( ⁇ -1) are used singly or in combination.
  • Examples of other monofunctional compounds ( ⁇ -2) include (meth) acrylic acid, crotonic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid, (meth) acrylamide-N-glycolic acid, and cinnamic acid.
  • Michael adduct of (meth) acrylic acid for example, acrylic acid dimer, methacrylic acid dimer, acrylic acid trimer, methacrylic acid trimer, acrylic acid tetramer, methacrylic acid tetramer, etc.
  • 2- (meth) acryloyloxyethyl dicarboxylic acid mono Esters eg, 2-acryloyloxyethyl succinic acid monoester, 2-methacryloyloxyethyl succinic acid monoester, 2-acryloyloxyethyl phthalic acid monoester, 2-methacryloyloxyethyl phthalic acid monoester, 2-acryloyloxyethyl Carboxyl group-containing unsaturated compounds such as oxahydrophthalic acid monoester and 2-methacryloyloxyethyl hexahydrophthalic acid monoester), 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acryl
  • Allyl compounds such as alkoxy (poly) alkylene glycol mono (meth) acrylates, N- (meth) acrylamidomethyltrimethylammonium chloride, allyltrimethylammonium chloride, dimethylallyl vinyl ketone, N-vinylpyrrolidone, vinyl propionate, Vinyl-based monomers such as vinyl stearate, vinyl chloride, vinylidene chloride, vinyl acetate and styrene, ( ⁇ -1) such as phenol ethylene oxide modified (meth) acrylate Outside (meth) acrylic acid alkyl ester compound, etc. can be mentioned, one selected from these or two or more may be used.
  • carboxyl group-containing unsaturated compounds preferably (meth) acrylic acid, crotonic acid, as other monofunctional compound ( ⁇ -2) in 100 parts of monofunctional compound (b3)
  • the active energy ray-curable component (B) at least one of the epoxy (meth) acrylate and urethane (meth) acrylate (b1), the polyfunctional compound (b2), and the monofunctional compound (b3). It is preferably at least one selected from the group consisting of, and particularly preferably contains all three components (b1) to (b3).
  • the content ratio of each component is 5 to 20% by weight of the component (b1) with respect to the whole active energy ray-curable component (B), particularly It is preferably 6 to 18% by weight, more preferably 7 to 16% by weight, and the component (b2) is 40 to 80% by weight, particularly 45 to 75% by weight, further 50 to 70% by weight, and (b3 ) Component is preferably set to 10 to 40% by weight, particularly 13 to 35% by weight, and more preferably 15 to 30% by weight.
  • At least one of the epoxy (meth) acrylate and urethane (meth) acrylate (b1) imparts mechanical properties to the coating film, and is a component that affects the surface hardness and flexibility. Therefore, if the content ratio of the component (b1) is too small, the stickiness of the coating film becomes strong, the adhesiveness is too strong at the time of peeling, paper breakage occurs, and the blocking resistance of the coated paper is insufficient. On the contrary, if the amount is too large, the coating film surface hardness becomes too high, so that the coating film tends to crack when bent. Moreover, adhesiveness also falls and the tendency for appropriate adhesive strength not to be obtained is also seen.
  • the polyfunctional compound (b2) is a component having a role as a crosslinking agent, such as improving the reinforcing property. For this reason, if the content ratio of the component (b2) is too small, the cohesive strength of the resin is insufficient, the sticky feeling becomes strong and the glossiness is lowered, or the adhesiveness is too strong at the time of peeling, resulting in paper breakage. On the contrary, if the amount is too large, the cohesive force of the resin is increased and the adhesiveness tends to be weakened.
  • the monofunctional compound (b3) is an acrylic rubber dispersant, which is polymerized by irradiation with active energy rays such as ultraviolet rays to control the cohesive force and glass transition temperature (Tg) of the resin. It is an ingredient. For this reason, if the content ratio of the component (b3) is too small, the content ratio of the component (b1) or the component (b2) having the role of a crosslinking agent is relatively increased, so that the cohesive strength of the resin becomes too high. On the other hand, if the amount is too large, the cohesive strength of the resin is insufficient, and the smoothness of the coating film surface tends to be lost during peeling.
  • the photopolymerization initiator (C) used in the present invention is not particularly limited as long as it generates radicals by the action of active energy rays such as light, and is an intramolecular self-cleavage photopolymerization initiator or hydrogen abstraction. A type of photoinitiator is used.
  • Examples of the intramolecular self-cleaving type photopolymerization initiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropane-1- ON, 1- (4-Isopropylenephenyl) -2-hydroxy-2-methylpropan-1-one, 1- (4-dodecylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- ( 2-hydroxyethoxy) -phenyl (2-hydroxy-2-propyl) ketone, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, Benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl Ether, benzoin isobutyl ether, benzyldimethyl ketal, ⁇ -
  • Examples of the hydrogen abstraction type photopolymerization initiator include benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, 3,3′-dimethyl-4-methoxybenzophenone, 2,4 , 6-trimethylbenzophenone, 4-methylbenzophenone, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, camphorquinone, dibenzosuberone, 2-ethyl Anthraquinone, 3,3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone, benzyldimethyl ketal, 9,10-phenanthrenequinone, and the like.
  • benzophenone, methylbenzophenone, 2,4 6- trimethyl benzophenone are preferred.
  • triethanolamine, triisopropanolamine, 4,4'-dimethylaminobenzophenone (Michler ketone), 4,4'-diethylaminobenzophenone, 2-dimethylamino can be used as an auxiliary for the photopolymerization initiator (C).
  • Ethylbenzoic acid ethyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate (n-butoxy), isoamyl 4-dimethylaminobenzoate, 2-dimethylhexyl 4-dimethylaminobenzoate, 2,4-diethylthio It is also effective to use xanthone, 2,4-diisopropylthioxanthone and the like together.
  • the content of the photopolymerization initiator (C) is 10 to 30 parts, preferably 13 to 27 parts, particularly 16 to 25 parts with respect to 100 parts of the active energy ray-curable component (B). It is preferable. If the content of the photopolymerization initiator is less than the above lower limit value, the polymerization is likely to vary. Conversely, if the content exceeds the above upper limit value, the adhesiveness does not occur and it is not suitable for practical use.
  • Tackifiers such as group petroleum resins, styrene resins, xylene resins, polymerization inhibitors, viscosity modifiers, leveling agents, waxes, antifoaming agents, anti-aging agents, stabilizers, colorants, fine particle fillers And the like, and compounds that cause coloration or discoloration by irradiation with ultraviolet rays or radiation can be added.
  • the active energy ray-curable pressure-sensitive adhesive coating film forming composition of the present invention can be obtained.
  • composition for forming active energy ray-curable pressure-sensitive adhesive coating film is substantially free of water, an aqueous solvent or an organic solvent, and contains a carboxyl group-containing acrylic polymer (A) and a photopolymerization initiator (C Further, other components added as required are dissolved or uniformly dispersed in the active energy ray-curable component (B).
  • Such a composition for forming an active energy ray-curable pressure-bonded coating film includes a carboxyl group-containing acrylic polymer (A), an active energy ray-curable component (B), a photopolymerization initiator (C), and, if necessary, added.
  • Other components to be prepared can be prepared by heating and mixing at room temperature (about 25 ° C. ⁇ 10), and in some cases, from room temperature to 60 ° C.
  • the viscosity of the resulting active energy ray-curable pressure-sensitive adhesive coating film forming composition is preferably 100 to 500 mPa ⁇ s / 25 ° C. If the viscosity is too high, it tends to be difficult to apply uniformly, and conversely, if it is too low, the coating suitability deteriorates and it tends to be difficult to obtain a uniform coating film. Because.
  • the obtained active energy ray-curable pressure-sensitive adhesive film-forming composition is formed on a whole surface or a predetermined portion of a base paper such as a printing sheet or postcard paper, and a gravure coater, flexo coater, air knife coater, bar coater.
  • a base paper such as a printing sheet or postcard paper
  • a gravure coater, flexo coater, air knife coater, bar coater By applying an active energy ray to this, an adhesive layer that is appropriately cured is obtained.
  • attachment which has peelability is attained by superposing
  • Examples of the base paper to be coated with the coating film forming composition of the present invention include high-quality paper, medium-quality paper, rough paper, cotton paper, art paper, coated paper, lightweight coated paper, and plastic laminate. Examples thereof include paper, cloth, plastic laminate cloth, plastic film, and metal foil.
  • active energy ray in addition to electromagnetic waves such as far ultraviolet rays, ultraviolet rays, near ultraviolet rays, infrared rays, electromagnetic waves such as X-rays and ⁇ rays, electron beams, proton rays, neutron rays, etc. can be used. Curing by ultraviolet irradiation is advantageous because of the availability of the irradiation device and the price.
  • a high-pressure mercury lamp, ultrahigh-pressure mercury lamp, carbon arc lamp, metal halide lamp, xenon lamp, chemical lamp, electrodeless discharge lamp, or the like that emits light in the wavelength range of 150 to 450 nm can be used.
  • the exposure dose of the actinic energy ray is preferably at 500 mJ / cm 2 or more, particularly 1000 mJ / cm 2 or more, and further preferably not 1500 mJ / cm 2 or more.
  • This irradiation amount is too low, there is a tendency that the polymerization by active energy ray irradiation tends to vary.
  • the upper limit of the irradiation dose is usually 10,000 mJ / cm 2 . This is because if the irradiation amount is too large, there is a tendency that it is not practical due to the relationship between the apparatus and the cost.
  • the thickness of the adhesive layer obtained by coating is not limited in general because requirements vary depending on the application, but is preferably 5 to 200 ⁇ m, more preferably 10 to 150 ⁇ m. This is because if the thickness of the adhesive layer is too thin, the adhesive properties tend to be difficult to stabilize, and conversely, if it is too thick, adhesive residue tends to occur.
  • the reaction product was filtered and washed with a filter cloth having a mesh size of 10 ⁇ m and dried with a circulating hot air dryer at 50 ° C. to obtain a carboxyl group-containing acrylic polymer (component A).
  • the resulting carboxyl group-containing acrylic polymer had a weight average molecular weight (Mw) of 80,000 and a glass transition temperature of ⁇ 50 ° C.
  • the reaction product was dried at 70 ° C. for 12 hours using a dryer to obtain an acrylic polymer for a comparative example containing no carboxyl group.
  • the resulting acrylic polymer had a weight average molecular weight (Mw) of 400,000 and a glass transition temperature of ⁇ 40 ° C.
  • each active energy ray-curable pressure-sensitive coating film-forming composition was produced according to the following examples and comparative examples.
  • Example 1 13 parts of the carboxyl group-containing acrylic polymer obtained in Production Example 1, 13 parts of epoxy acrylate (trade name: “CN-116”; manufactured by Sartomer) as component (b1), and trimethylolpropane as the polyfunctional compound (b2) 22 parts of triacrylate, 40 parts of 1,6-hexanediol diacrylate, 11 parts of n-butyl acrylate as monofunctional compound (b3), 2-hydroxy-3-phenoxypropyl acrylate (trade name: “Aronix M-5700”; 14 parts of Toa Gosei Co., Ltd. was placed in a container equipped with a stirrer and stirred and mixed for 24 hours to dissolve. The viscosity of this solution was 150 mPa ⁇ s / 25 ° C.
  • Example 2 14 parts of the carboxyl group-containing acrylic polymer obtained in Production Example 1, 26 parts of trimethylolpropane triacrylate as the polyfunctional compound (b2), 43 parts of 1,6-hexanediol diacrylate, and n as the monofunctional compound (b3) -Active energy ray-curable type in the same manner as in Example 1 except that 14 parts of butyl acrylate and 17 parts of 2-hydroxy-3-phenoxypropyl acrylate (trade name: “Aronix M-5700”; manufactured by Toagosei Co., Ltd.) are used. A composition for forming a pressure-bonded coating film was obtained.
  • Example 3 14 parts of a carboxyl group-containing acrylic polymer obtained in Production Example 1, 14 parts of epoxy acrylate (trade name: “CN-116”; manufactured by Sartomer) as component (b1), 63 parts of 1,6-hexanediol diacrylate Example 1 except that 10 parts of n-butyl acrylate and 13 parts of 2-hydroxy-3-phenoxypropyl acrylate (trade name: “Aronix M-5700”; manufactured by Toagosei Co., Ltd.) were used as the monofunctional compound (b3).
  • an active energy ray-curable pressure-sensitive adhesive coating film-forming composition was obtained.
  • Example 1 Active energy ray curing is carried out in the same manner as in Example 1 except that the photopolymerization initiator is 6 parts of 1-hydroxy-cyclohexyl-phenyl-ketone (trade name “Irgacure 184”; manufactured by Ciba Specialty Chemicals). A composition for forming a pressure-bonded coating film was obtained.
  • Example 2 Example 1 except that the photopolymerization initiator was 6 parts of 2-hydroxy-2-methyl-phenyl-propan-1-one (trade name “D-1173”; manufactured by Ciba Specialty Chemicals). Thus, an active energy ray-curable pressure-sensitive adhesive film-forming composition was obtained.
  • Example 4 An active energy ray-curable pressure-sensitive adhesive film-forming composition was obtained in the same manner as in Example 1, except that the acrylic polymer for Comparative Example obtained in Production Example 2 was used. In addition, the viscosity of the solution before adding a photoinitiator was 1300 mPa * s / 25 degreeC.
  • Table 1 below shows the blending ratios of the above component materials used in Examples and Comparative Examples.
  • a peelable adhesive-processed paper was produced by the following method. Coated paper weighing 110g / m 2, coating the obtained active energy ray-curable obtained in Examples and Comparative Examples at a rate of 7 g / m 2 crimp coating forming composition by a wire bar, to ultraviolet radiation An adhesive layer was formed by curing to obtain each peelable adhesive processed paper.
  • the ultraviolet irradiation conditions are a high-pressure mercury lamp, an irradiation intensity of about 200 W / m 2 , an integrated illuminance of 60 mJ / m 2 , and a lamp height of 18 cm.
  • ⁇ Curing property> The stickiness and hardness of the coated surface of the peelable adhesive processed paper were confirmed, and the cured state of the adhesive layer was determined according to the following criteria. ⁇ : There is no stickiness and the curing is sufficiently completed. (Triangle
  • the peelable adhesive-treated paper is cut into a width of 25 mm and a length of 100 mm, and the coated surfaces are combined with each other in two layers, and are pressure-bonded using a laminator with a pressure of 0.2 MPa, and a sample having a width of 25 mm ( Pressure temporary adhesive paper).
  • the adhesiveness was evaluated using each pressure temporary adhesive paper obtained above.
  • peelability was evaluated by the following method using the pressure temporary adhesive paper.
  • a T type A peel test was performed.
  • X Adhered, and if it is peeled off, the paper is torn. -: Not determined from the beginning because it is not bonded.
  • Table 2 below shows the evaluation results of the coating property, curability, adhesiveness, and peelability obtained above.
  • Example 2 the peelable adhesive processed paper obtained in Example 1 was excellent in coatability, curability, adhesiveness, peelability, and highly practical.
  • Example 2 both the epoxy (meth) acrylate and the urethane (meth) acrylate, which are the components (b1), are not blended.
  • Example 3 only one kind of the polyfunctional compound (b2) is blended.
  • the coating property and curability were good
  • Example 3 the coating property and adhesiveness were good, and other physical properties such as peelability were practical.
  • the drying process at the time of coating was unnecessary, and the surface gloss which was excellent in the printing surface was seen.
  • Comparative Examples 1 to 3 which are general photopolymerization initiator contents, were not sufficiently adhesive due to poor curing. Moreover, since the comparative example 4 using the acrylic polymer which does not contain a carboxyl group has bad mixability of the composition for pressure-bonding coating film formation, is inferior in coating property, and adhesiveness is too high, if it tries to peel off The paper was torn.
  • composition for forming an active energy ray-curable pressure-bonded coating film of the present invention is used as an adhesive used in a postcard system having a confidentiality instead of a sealed letter for the purpose of reducing postage costs, printing information and automating the creation of a notice. It is useful and can also be used as a double-sided tape or an adhesive tape by coating on a base material sheet such as a nonwoven fabric or a foam base material.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Paper (AREA)

Abstract

La présente invention concerne une composition pour former un film de revêtement pour liaison par contact, de type durcissable par rayonnement d'énergie actinique, comprenant un polymère acrylique carboxylé (A), un ingrédient durcissable par rayonnement d'énergie actinique (B) et un initiateur de photopolymérisation (C), la teneur en initiateur de photopolymérisation (C) étant de 10 à 30 parties en poids pour 100 parties en poids de l'ingrédient durcissable par rayonnement d'énergie actinique (B). La composition peut donc être appliquée de façon satisfaisante et ne nécessite pas d'étape de séchage après l'application, ce qui permet ainsi d'améliorer l'efficacité de traitement. La composition peut durcir de façon satisfaisante. Suite à son durcissement, la composition présente une remarquable force d'adhérence et une très bonne aptitude au décollement lors du décollement. En conséquence, un papier revêtu d'un adhésif décollable obtenu à partir de cette composition combine une remarquable force d'adhérence et une bonne aptitude au décollement, ce qui le rend très pratique.
PCT/JP2008/073332 2007-12-28 2008-12-22 Composition pour former un film de revêtement pour liaison par contact, de type durcissable par rayonnement d'énergie actinique et papier revêtu d'un adhésif décollable l'utilisant WO2009084511A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020107007582A KR101530400B1 (ko) 2007-12-28 2008-12-22 활성 에너지선 경화형 압착 도막 형성용 조성물과 이를 사용한 박리성 접착 가공지
CN200880115150XA CN101855310B (zh) 2007-12-28 2008-12-22 活性能量射线固化型压敏粘合涂膜形成用组合物及使用该组合物的剥离性粘合加工纸

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007-340017 2007-12-28
JP2007340017A JP5528669B2 (ja) 2007-12-28 2007-12-28 活性エネルギー線硬化型圧着塗膜形成用組成物およびそれを用いた剥離性接着加工紙。

Publications (1)

Publication Number Publication Date
WO2009084511A1 true WO2009084511A1 (fr) 2009-07-09

Family

ID=40824225

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/073332 WO2009084511A1 (fr) 2007-12-28 2008-12-22 Composition pour former un film de revêtement pour liaison par contact, de type durcissable par rayonnement d'énergie actinique et papier revêtu d'un adhésif décollable l'utilisant

Country Status (4)

Country Link
JP (1) JP5528669B2 (fr)
KR (1) KR101530400B1 (fr)
CN (1) CN101855310B (fr)
WO (1) WO2009084511A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111548751A (zh) * 2019-02-12 2020-08-18 日东电工株式会社 增强薄膜、装置的制造方法以及增强方法
JP2021091909A (ja) * 2016-04-20 2021-06-17 東洋インキＳｃホールディングス株式会社 活性エネルギー線重合性接着剤および積層体
US11613677B2 (en) 2017-12-15 2023-03-28 Lg Chem, Ltd. Water-based acrylic pressure-sensitive adhesive for clothing, and preparation method thereof

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5344038B2 (ja) * 2009-07-08 2013-11-20 東亞合成株式会社 厚塗り用塗料組成物
JP6051662B2 (ja) * 2012-08-03 2016-12-27 日立化成株式会社 回路接続用接着剤組成物、接着シート、接着剤リール及び回路部材の接続構造体
JP6062806B2 (ja) * 2013-05-31 2017-01-18 昭和電工株式会社 ガラスエッチング向け再剥離保護テープ用活性線硬化型粘着剤組成物、ガラスエッチング向け再剥離保護テープ

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06346026A (ja) * 1993-06-10 1994-12-20 Mitsui Toatsu Chem Inc 活性エネルギー線硬化型ホットメルト感圧接着剤組成物およびこれを用いた粘着製品と粘着製品の製造方法
JPH108267A (ja) * 1996-06-27 1998-01-13 Nitto Denko Corp レジスト膜画像の除去方法とレジスト除去用接着材料
JP2000212526A (ja) * 1999-01-25 2000-08-02 Lintec Corp 粘着シ―ト
JP2000223453A (ja) * 1999-02-02 2000-08-11 Nitto Denko Corp 半導体ウエハ保護用粘着シート及び半導体ウエハの研削方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4030630B2 (ja) * 1997-11-05 2008-01-09 リンテック株式会社 粘着シート及び粘着シートの貼合方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06346026A (ja) * 1993-06-10 1994-12-20 Mitsui Toatsu Chem Inc 活性エネルギー線硬化型ホットメルト感圧接着剤組成物およびこれを用いた粘着製品と粘着製品の製造方法
JPH108267A (ja) * 1996-06-27 1998-01-13 Nitto Denko Corp レジスト膜画像の除去方法とレジスト除去用接着材料
JP2000212526A (ja) * 1999-01-25 2000-08-02 Lintec Corp 粘着シ―ト
JP2000223453A (ja) * 1999-02-02 2000-08-11 Nitto Denko Corp 半導体ウエハ保護用粘着シート及び半導体ウエハの研削方法

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021091909A (ja) * 2016-04-20 2021-06-17 東洋インキＳｃホールディングス株式会社 活性エネルギー線重合性接着剤および積層体
JP7070733B2 (ja) 2016-04-20 2022-05-18 東洋インキＳｃホールディングス株式会社 活性エネルギー線重合性接着剤および積層体
JP2022093410A (ja) * 2016-04-20 2022-06-23 東洋インキＳｃホールディングス株式会社 活性エネルギー線重合性接着剤および積層体
JP2022093411A (ja) * 2016-04-20 2022-06-23 東洋インキＳｃホールディングス株式会社 活性エネルギー線重合性接着剤および積層体
JP7318767B2 (ja) 2016-04-20 2023-08-01 東洋インキＳｃホールディングス株式会社 活性エネルギー線重合性接着剤および積層体
US11613677B2 (en) 2017-12-15 2023-03-28 Lg Chem, Ltd. Water-based acrylic pressure-sensitive adhesive for clothing, and preparation method thereof
EP3650513B1 (fr) * 2017-12-15 2024-01-31 Lg Chem, Ltd. Adhésif acrylique sensible à la pression à base d'eau pour vêtements et son procédé de préparation
CN111548751A (zh) * 2019-02-12 2020-08-18 日东电工株式会社 增强薄膜、装置的制造方法以及增强方法

Also Published As

Publication number Publication date
CN101855310A (zh) 2010-10-06
CN101855310B (zh) 2013-08-07
KR20100102091A (ko) 2010-09-20
JP2009161603A (ja) 2009-07-23
JP5528669B2 (ja) 2014-06-25
KR101530400B1 (ko) 2015-06-19

Similar Documents

Publication Publication Date Title
JP5954972B2 (ja) 粘着剤組成物、粘着剤、およびそれを用いてなる粘着シート
JP3384979B2 (ja) 感圧性両面接着テープ及びその製造方法
JP5528669B2 (ja) 活性エネルギー線硬化型圧着塗膜形成用組成物およびそれを用いた剥離性接着加工紙。
JP2007191671A (ja) 樹脂組成物、光学部材用粘着剤、光学部材用粘着剤の製造方法
JP6556550B2 (ja) 光硬化性粘着剤組成物
JP4936908B2 (ja) 活性エネルギー線重合性組成物、粘着剤、および粘着テープ
JP5530621B2 (ja) 紫外線重合性粘着剤組成物、紫外線重合性粘着剤組成物を用いた感圧性接着剤及びこの感圧性接着剤を用いた接着シ―ト
JP2004210879A (ja) 再剥離性粘着加工紙用組成物および再剥離性粘着加工紙
JP3797628B2 (ja) 感圧接着剤及びその接着シート
JP3413795B2 (ja) 活性エネルギー線硬化性樹脂組成物および剥離帳票シート用コーティング剤
JP2007091818A (ja) 紫外線硬化型再剥離性圧着組成物及び再剥離性接着加工紙
JP2007231103A (ja) 紫外線硬化型再剥離性圧着組成物及び再剥離性接着加工紙
JP6132463B2 (ja) 粘着剤組成物、粘着剤、およびそれを用いてなる粘着シート
JP2012025807A (ja) アクリル系粘着剤、粘着シート、アクリル系樹脂組成物
JP2007091816A (ja) 紫外線硬化型再剥離性圧着組成物及び再剥離性接着加工紙
JP4582731B2 (ja) Ｕｖ硬化型感圧接着剤
JP2007091817A (ja) 紫外線硬化型再剥離性圧着組成物及び再剥離性接着加工紙
JP2873352B2 (ja) 感圧接着剤
JP4563518B2 (ja) 剥離帳票シート用活性エネルギー線硬化性コーティング剤
JP2007217452A (ja) 紫外線硬化型再剥離性圧着組成物及び再剥離性接着加工紙
JP3384980B2 (ja) 無基材感圧性両面接着テープ・シート及びその製造方法
JP3537070B2 (ja) 接着剤組成物及びそれを用いた情報担体シート
JP4362799B2 (ja) 再剥離性情報シート
JP2007231102A (ja) 紫外線硬化型再剥離性圧着組成物及び再剥離性接着加工紙
JP4847742B2 (ja) 活性エネルギー線硬化型圧着ニス組成物および再剥離性情報シート

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200880115150.X

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 08868839

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 20107007582

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 08868839

Country of ref document: EP

Kind code of ref document: A1