WO2008032677A1 - Composition de résine polymérisable par voie radicalaire pour un revêtement ou un adhésif - Google Patents
Composition de résine polymérisable par voie radicalaire pour un revêtement ou un adhésif Download PDFInfo
- Publication number
- WO2008032677A1 WO2008032677A1 PCT/JP2007/067594 JP2007067594W WO2008032677A1 WO 2008032677 A1 WO2008032677 A1 WO 2008032677A1 JP 2007067594 W JP2007067594 W JP 2007067594W WO 2008032677 A1 WO2008032677 A1 WO 2008032677A1
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- WIPO (PCT)
- Prior art keywords
- resin composition
- resin
- meth
- parts
- radically polymerizable
- Prior art date
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- 239000011347 resin Substances 0.000 claims abstract description 67
- -1 diisocyanate compound Chemical class 0.000 claims abstract description 66
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- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 claims description 4
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- 239000003795 chemical substances by application Substances 0.000 description 27
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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- 239000004925 Acrylic resin Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 230000001771 impaired effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000002165 photosensitisation Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- 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
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
Definitions
- the present invention relates to a radically polymerizable resin composition for coating adhesion, which comprises a polycarbonate skeleton-containing urethane resin containing a (meth) atalyloyl group and a radically polymerizable unsaturated monomer having a specific skeleton.
- the present invention relates to an adhesion method and an adhesive for butyl resin.
- Urethane resins containing a (meth) atallyloyl group having a polyether and / or polyester skeleton in the main skeleton are highly flexible and are used as base resins for adhesives to various substrates, and are adhesives for fiber-reinforced plastics. It is known that it is useful as (see Patent Document 1).
- Patent Document 1 JP 2004-238557 A
- Patent Document 2 JP-A 63-118388
- these base resins for adhesives are not only excellent in adhesion to all plastic base materials, but are currently widely used in agriculture and sewage systems. Excellent adhesion performance when used alone! / ,!
- the radical polymerizable resin is bonded to the so-called soft chlorinated resin containing a plasticizer in particular by surface sanding, heat fusion, or the like.
- the adhesive using an organic solvent has a problem that it is not preferable from the viewpoint of solvent volatilization.
- An object of the present invention is to provide an adhesive that can be used without selecting an adherend in a radically polymerizable resin that has conventionally had a problem of selecting an adherend when used for bonding. It is in the development of agents.
- a radical polymerizable resin composition exhibiting excellent adhesion performance to a soft chlorinated resin, a structure using the resin composition and a chlorinated resin, a coating material mainly composed of the resin composition, and the resin
- the polycarbonate diol (A1) and the diisocyanate compound (A2) are reacted to obtain an isocyanate group-containing compound (A3), and then the above (A3) and one hydroxide
- a urethane polymerizable resin having a polycarbonate skeleton having a (meth) acryloyl group obtained by reacting a (meth) acrylic compound containing a group (A) and a radically polymerizable unsaturated monomer having a dicyclopentyl group
- the present invention provides a radically polymerizable resin composition for coating adhesion, comprising (B).
- the present invention also provides a structure characterized in that a salted bull resin layer is provided on a substrate via the above-mentioned radically polymerizable resin composition for coating adhesion.
- the present invention also provides a method for adhering a chlorinated bull resin to a substrate, characterized by using the radically polymerizable resin composition for coating adhesion.
- the present invention also provides a coating material comprising the radically polymerizable resin composition for coating adhesion as a main component.
- the present invention also provides an adhesive comprising the radically polymerizable resin composition for coating adhesion as a main component.
- a hard chloride resin and a soft chloride resin, or a polychlorinated resin it is possible to bond a hard chloride resin and a soft chloride resin, or a polychlorinated resin to a substrate with excellent adhesion performance. It can also be used as a coating material (primer, paint, sealing material, note) of poly (vinyl chloride) resin.
- (A) has at least one (meth) atalyloyl group in the molecule.
- Such resins are poly
- the carbonate diol (Al) and the diisocyanate compound (A2) are preferably reacted so that the equivalent ratio of the isocyanate group to the hydroxyl group (NCO / OH) is 1.5 to 2 to obtain the isocyanate group-containing compound (A3).
- the (A3) and the (meth) acrylic compound (A4) containing one hydroxyl group preferably have an equivalent ratio (NCO / OH) of the isocyanate group to the hydroxyl group substantially the same. It is obtained by reacting each compound as follows.
- the polycarbonate diol (A1) here is, for example, an ester exchange reaction between an aliphatic chain diol and / or an alicyclic diol and a carbonate such as dimethyl carbonate or jetyl carbonate, or a cyclic carbonate having an alkylene group.
- a ring opening reaction of phosgene and an aliphatic chain diol and / or an alicyclic diol, etc. preferably a number average molecular weight of 300 to 3000, particularly preferably ⁇ (or in the range of 500 to 2000).
- the molecular weight is in the range of 300 to 3000, preferably S. If it is less than 300, the characteristics derived from the carbonate will be weak, and if it is greater than 3000, it will react with the polyisocyanate. The viscosity of the obtained compound is increased and it is difficult to work practically.
- the aliphatic chain diol and / or alicyclic diol used as a raw material for the production of carbonate diol (A1) has an arbitrary structure.
- carbonate diol (A1) Conventionally known polyoxypropylene di-diol, polytetramethylene glycol Polyesterol polyols such as lime-ximethylene di-nore, or polyester polyols, which are condensates of polyhydric alcohols and polybasic carboxylic acids, can also be used in combination with polycarbonate diols to react with diisocyanate compounds ( ⁇ 2).
- (A1) is contained in an amount of 60% by mass or more, more preferably 90% by mass or more.
- the diisocyanate compound ( ⁇ 2) is a compound having an isocyanate group in the molecule. It refers to what you have.
- diisocyanate compound (A2) examples include 2,4-tolylene diisocyanate, its isomer or a mixture of these isomers (hereinafter abbreviated as TDI), diphenylmethane diisocyanate, hexamethylene diiso- sane. Cyanate, isophorone diisocyanate (hereinafter abbreviated as IPDI), xylylene diisocyanate, hydrogenated xylylene diisocyanate, dicyclohexyl. These can be used alone or in combination of two or more. Of the diisocyanate compound (A2), an aliphatic compound having two isocyanate groups is particularly preferred from the viewpoint of the weather resistance discoloration obtained.
- TDI 2,4-tolylene diisocyanate, its isomer or a mixture of these isomers
- IPDI isophorone diisocyanate
- xylylene diisocyanate hydrogenated xylylene diisocyan
- a hydroxyl group-containing (meth) acrylic ester is preferably used.
- the polymerizable unsaturated monomer (B) used in the present invention is a radically polymerizable unsaturated monomer having a dicyclopentyl group in the skeleton.
- force S including dicyclopentuoxychetyl (meth) acrylate, dicyclopentyl (meth) acrylate, dicyclopentanyl (meth) acrylate, and other radical polymerizable monomers
- a hydroxyl group-containing allyl ether compound is used in combination with the (meth) acrylic compound (A4) containing one hydroxyl group for the purpose of preventing curability inhibition by air during curing. It can also be used.
- the radical polymerizable resin composition of the present invention contains the polycarbonate skeleton-containing urethane resin (A) and the polymerizable unsaturated monomer (B).
- the polycarbonate skeleton-containing urethane resin (A) 90 to 10 parts by mass and the polymerizable unsaturated monomer (B) 10 to 90 parts by mass are preferably dissolved together.
- a polymerization inhibitor to the resin composition of the present invention.
- the polymerization inhibitor include trihydroquinone, hydroquinone, 1,4-naphthoquinone, parabenzoquinone, and tonolhydride. Mouth non, p tert butynole power teconore, 2, 6 tert butynole 4-methylphenol and the like.
- the amount of the polymerization inhibitor used is preferably 10 to 1000 ppm in the resin composition.
- the resin composition of the present invention is usually cured by adding a known curing agent that generates radicals.
- the curing agent that can be added include one or more selected from ultraviolet curing agents, electron beam curing agents, photocuring agents, and thermosetting agents.
- the amount of the curing agent used is preferably 0.;! To 10 parts by mass with respect to 100 parts by mass of the resin composition; more preferably 5 to 5 parts by mass.
- the ultraviolet curing agent is a photosensitizing substance.
- benzoin ethers such as benzoin alkyl ethers
- benzophenones such as benzophenone and methyl orthobenzoylbenzoate
- benzyl dimethyl ketal 2,2 diethoxyacetophenone, 2 hydroxy-2 methyl
- Acetophenones such as propiophenone, 4-isopropyl-1-hydroxy-1-2-methylpropiophenone, 1,1-dichloroacetophenone; 2-chlorothioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, etc.
- thixanthone series examples of the electron beam curing agent include halogenated alkylbenzenes and disulfide compounds.
- Examples of the photocuring agent include hydroxyalkylphenone compounds, alkylthioxanthone compounds, sulfonium salt compounds, and acylphosphine oxide compounds.
- thermosetting agent examples include organic peroxides. Specifically, for example, known peroxy peroxides, peroxyesters, hydride peroxides, dialkyl peroxides, ketone peroxides, peroxyketals, alkyl peresters, percarbonates, etc. Can be used and is appropriately selected depending on kneading conditions, curing temperature, and the like.
- the resin composition of the present invention may be used in combination with a known accelerator such as an organic metal salt such as cobalt naphthenate or otetenate, an amine or ⁇ -diketone as a curing accelerator.
- a known accelerator such as an organic metal salt such as cobalt naphthenate or otetenate, an amine or ⁇ -diketone as a curing accelerator.
- the resin composition of the present invention includes generally known unsaturated polyester resins, bururetan resins, burester urethane resins, polyisocyanates, polyepoxides, talyl resins, alkyd resins, urea resins. , Melamine resins, poly (butyl acetate), vinyl acetate copolymers, polygen elastomers, saturated polyesters, saturated polyethers; senorelose derivatives such as nitrosenorose and senorerose acetate butyrate; Other conventional natural and synthetic polymer compounds such as oils such as tung oil, soybean oil, castor oil, epoxidized oil and the like can be added as long as the effects of the present invention are not impaired.
- glass fiber, carbon fiber, organic fiber, metal fiber and the like can be added to the resin composition of the present invention as a reinforcing material in an amount of 5 to 70 mass%.
- the resin composition of the present invention contains a filler such as calcium carbonate, talc, my strength, clay, silica powder, colloidal silica, barium sulfate, aluminum hydroxide, glass powder, glass beads, and crushed sand. Can be used as a sealing agent, paint, or coating material. It is also effective as a material for impregnating and reinforcing cloth and kraft paper. Furthermore, other known additives such as zinc stearate, titanium white, zinc white, various other pigments, dyes, stabilizers, flame retardants and the like can be added. [0024]
- the radically polymerizable resin composition for coating adhesion of the present invention is preferably used for a portion having polychlorinated bulls.
- Forces suitable for applications requiring coating adhesion, such as film laminating material, putty, paste, adhesive resin using fiber reinforcing material, and ink vehicle are not particularly limited thereto.
- the base material is a soft chloride resin, a hard chloride resin, or metal, fiber, paper, leather, and plastic, and particularly for applications in which the chloride resin and the substrate are firmly bonded and coated. It can be used.
- the resin composition of the present invention exhibits excellent adhesion performance even to a chlorinated resin, particularly a soft chlorinated chloric resin, for which a conventional adhesive could not exhibit good adhesion performance. Therefore, the structure of the present invention in which the chlorinated resin layer is provided on the base material through the resin composition of the present invention is a material that makes use of this excellent adhesion performance. It is stably immobilized on the top.
- the method for adhering butyl chloride resin to a base material using the resin composition of the present invention is an excellent method which has not been conventionally used. As a bonding method at this time, a known method may be applied except that the resin composition of the present invention is used as an adhesive.
- the structure of the present invention is formed by laminating the base material, the resin composition of the present invention, and a chlorinated resin in this order.
- a known epoxy-based, urethane-based, isocyanate-based, acrylic-based or aqueous dispersion primer may be used between the substrate and the resin composition of the present invention.
- the reaction was carried out at 90 ° C for 7 hours. Since NCO% was 0.3 mass% or less, 0.05 part of hydroquinone was added to obtain a polycarbonate skeleton-containing urethane resin having a methacryloyl group.
- the adhesive performance of the resin composition was evaluated by using a chlorinated resin (hereinafter abbreviated as PVC) as a base material.
- PVC chlorinated resin
- a hard vinyl chloride resin (hard PVC, manufactured by Takiron, 3mm thickness, gray color) as a base material was cut into a vertical length of 100mm and a width of 25mm, and the surface was lightly degreased with acetone to remove dust. . Thereafter, the above-mentioned various resin compositions are applied to the two test pieces so that the adhesion area is 25 mm ⁇ 25 mm, and the adhesive part is shifted until the resin composition is cured, and the weight is placed on the test piece and cured. Further, the resin composition was completely cured by placing it in a dryer at 60 ° C. for 1 hour.
- the adhesion evaluation test was conducted by a tensile shear (tensile speed 5 mm / min) test according to JIS-K 6850, and the shear strength and the state of the adhesion interface after the test were observed. The case where the hard PVC substrate was destroyed by the test was indicated as substrate failure. If it peels off at the substrate interface! /, The adhesive performance is inferior and the evaluation judgment is poor: X. If the adhesive strength is superior to the base material strength and the base material breaks, the evaluation judgment is made. Good: ⁇ .
- Soft PVC is made by adding 50 parts of dioctyl phthalate as a plasticizer to 100 parts of vinyl chloride resin powder (Shinichi Dai-ichi Vinyl Co., Ltd. ZEST1000Z), and then adding 2 parts of powdered barium zinc-based stabilizer at room temperature to 170 ° C. The mixture was uniformly melt-kneaded for 5 minutes with a heating mixing roll, to obtain a soft PVC sheet having a thickness of about 1 mm.
- the obtained flexible PVC sheet was cut into strips with a length of 200 mm and a width of 25 mm, and each of the above resin compositions was evenly applied to an area with a length of 150 mm and a width of 25 mm.
- the test piece was piled up and held lightly while removing air bubbles, and the test piece was sandwiched between two glass plates to cure the resin composition. Thereafter, the test piece was sandwiched between glass plates and placed in a dryer at 60 ° C. for 1 hour to completely cure the resin composition.
- the adhesion evaluation test was conducted in accordance with JIS-K-6854, and the 180 ° peel test (T-peel test, 10 mmZ min) was used to observe the line and peel strength and the state of the adhesive interface after the test. According to the test, when only one side of the adhesive is adhered and the interface peels off, it is judged as bad: X, and the adhesive layer itself is broken and adheres to both sides of the substrate. Was evaluated as good: ⁇ .
- the resin composition of the present invention was excellent in adhesion between hard PVC base materials and between soft PVC base materials that could not be bonded with conventional adhesives. It was found to exhibit adhesive properties.
- the surface of a cold-rolled steel plate (2 mm thick, JISG3141 SPCC—SD) used as a base material is degreased with acetone, and primer PD (trade name, manufactured by Dainippon Ink & Chemicals, Inc.), a primer based on isocyanate, is applied to the brush. And then dried at room temperature for 1 hour.
- primer PD trade name, manufactured by Dainippon Ink & Chemicals, Inc.
- the resin composition to which the accelerator and the curing agent prepared previously were uniformly applied was applied to the surface of the steel plate, and immediately, the sheet-like soft salt-vinyl resin (used in the adhesive evaluation section) ( Soft PVC) was placed in a layer without air, allowed to stand at room temperature for 1 day, and cured to produce a structure comprising a soft vinyl chloride resin sheet resin composition Z steel plate substrate of the present invention.
- Soft PVC sheet-like soft salt-vinyl resin
- the soft salt vinyl resin sheet was integrated with the steel plate substrate by the resin composition of the present invention. . As a result, it could not be easily peeled off, and an integrated structure of a soft vinyl chloride resin sheet and a steel plate substrate was obtained.
- primer PD (trade name, manufactured by Dainippon Ink & Chemicals, Inc.), which is an isocyanate primer, was applied to the surface using a brush and dried at room temperature for 1 hour to prepare a concrete board.
- the soft chloride resin sheet was integrated with the concrete board substrate by the resin composition of the present invention. As a result, it could not be easily peeled off, and an integrated structure of a soft chloride resin sheet and a concrete board substrate was obtained.
- the resin composition film of the present invention was peeled off from the end of the bull chloride resin base material using a cutter blade, but it was sufficiently adhered to the base material and did not peel off. Together, I confirmed that!
- the hard chloride resin and the conventional adhesive are excellent. It is useful because it can provide a radically polymerizable resin composition for coating adhesion that exhibits excellent adhesion performance even for soft chlorinated resin that could not be adhered. And since the resin composition of this invention can be apply
- the present invention is particularly applicable to adhesion of various types of chlorinated resin to a substrate and covering of various types of chlorinated resin.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006250810A JP4180626B2 (ja) | 2006-09-15 | 2006-09-15 | 構造物、及び軟質塩化ビニル樹脂の基材への接着方法 |
| JP2006-250810 | 2006-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2008032677A1 true WO2008032677A1 (fr) | 2008-03-20 |
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ID=39183736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2007/067594 WO2008032677A1 (fr) | 2006-09-15 | 2007-09-10 | Composition de résine polymérisable par voie radicalaire pour un revêtement ou un adhésif |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP4180626B2 (enrdf_load_stackoverflow) |
| WO (1) | WO2008032677A1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012017510A1 (ja) * | 2010-08-02 | 2012-02-09 | リケンテクノス株式会社 | 塗料および積層体 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5335262B2 (ja) * | 2008-03-25 | 2013-11-06 | 第一工業製薬株式会社 | エネルギー線硬化型樹脂組成物およびそれを用いた塗料 |
| JP2010129960A (ja) | 2008-12-01 | 2010-06-10 | Sony Chemical & Information Device Corp | 接続フィルム、並びに、接合体及びその製造方法 |
| JP5445215B2 (ja) * | 2009-02-24 | 2014-03-19 | 三菱化学株式会社 | 活性エネルギー線硬化性樹脂組成物、硬化膜及び積層体 |
| JP5447204B2 (ja) * | 2009-06-15 | 2014-03-19 | 東洋インキＳｃホールディングス株式会社 | （メタ）アクリロイル基を有するウレタン樹脂及び該ウレタン樹脂を含有する活性エネルギー線硬化性接着剤、並びに太陽電池用裏面保護シート |
| CN102898958B (zh) * | 2011-07-25 | 2016-11-02 | 汉高股份有限公司 | 一种粘合剂组合物 |
| US20250230338A1 (en) * | 2022-03-10 | 2025-07-17 | Kansai Paint Co., Ltd. | Thermosetting coating material composition, coated article, and in-mold coating method |
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| JP2000063766A (ja) * | 1998-08-20 | 2000-02-29 | Jsr Corp | 光ディスク用接着剤 |
| JP2004238557A (ja) * | 2003-02-07 | 2004-08-26 | Dainippon Ink & Chem Inc | 硬化性接着剤及びそれを用いた接着方法 |
| JP2005171154A (ja) * | 2003-12-12 | 2005-06-30 | Mitsubishi Rayon Co Ltd | 硬化性組成物、金属保護コーティング材、および光ディスク用接着剤 |
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|---|---|---|---|---|
| JPH05125330A (ja) * | 1991-11-08 | 1993-05-21 | Toagosei Chem Ind Co Ltd | 光硬化型接着剤 |
| JP3841232B2 (ja) * | 1996-06-05 | 2006-11-01 | Ｊｓｒ株式会社 | 塗膜形成用組成物 |
-
2006
- 2006-09-15 JP JP2006250810A patent/JP4180626B2/ja active Active
-
2007
- 2007-09-10 WO PCT/JP2007/067594 patent/WO2008032677A1/ja active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000063766A (ja) * | 1998-08-20 | 2000-02-29 | Jsr Corp | 光ディスク用接着剤 |
| JP2004238557A (ja) * | 2003-02-07 | 2004-08-26 | Dainippon Ink & Chem Inc | 硬化性接着剤及びそれを用いた接着方法 |
| JP2005171154A (ja) * | 2003-12-12 | 2005-06-30 | Mitsubishi Rayon Co Ltd | 硬化性組成物、金属保護コーティング材、および光ディスク用接着剤 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012017510A1 (ja) * | 2010-08-02 | 2012-02-09 | リケンテクノス株式会社 | 塗料および積層体 |
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| Publication number | Publication date |
|---|---|
| JP2008069307A (ja) | 2008-03-27 |
| JP4180626B2 (ja) | 2008-11-12 |
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