JP5418868B1 - 活性エネルギー線硬化型水性樹脂組成物、活性エネルギー線硬化型水性塗料、及び該塗料で塗装された物品 - Google Patents
活性エネルギー線硬化型水性樹脂組成物、活性エネルギー線硬化型水性塗料、及び該塗料で塗装された物品 Download PDFInfo
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- JP5418868B1 JP5418868B1 JP2013528436A JP2013528436A JP5418868B1 JP 5418868 B1 JP5418868 B1 JP 5418868B1 JP 2013528436 A JP2013528436 A JP 2013528436A JP 2013528436 A JP2013528436 A JP 2013528436A JP 5418868 B1 JP5418868 B1 JP 5418868B1
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 120
- 239000000178 monomer Substances 0.000 claims abstract description 76
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 63
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- 150000001875 compounds Chemical class 0.000 claims abstract description 32
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- 239000003054 catalyst Substances 0.000 description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002649 leather substitute Substances 0.000 description 4
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- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- YOSXAXYCARLZTR-UHFFFAOYSA-N prop-2-enoyl isocyanate Chemical compound C=CC(=O)N=C=O YOSXAXYCARLZTR-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- ZKDDJTYSFCWVGS-UHFFFAOYSA-M sodium;diethoxy-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Na+].CCOP([S-])(=S)OCC ZKDDJTYSFCWVGS-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- YYBMRDFADFQHGU-UHFFFAOYSA-N tert-butyl (2-methylpropan-2-yl)oxy carbonate Chemical class CC(C)(C)OOC(=O)OC(C)(C)C YYBMRDFADFQHGU-UHFFFAOYSA-N 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229940035024 thioglycerol Drugs 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-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
- C09D133/00—Coating compositions 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; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—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
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
-
- 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
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/02—Emulsion paints including aerosols
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
- C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
-
- 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
- C08G18/673—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester groups
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/06—Polyurethanes from polyesters
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- C09D133/00—Coating compositions 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; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—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
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/066—Copolymers with monomers not covered by C09D133/06 containing -OH groups
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- C09D133/00—Coating compositions 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; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
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- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
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- 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
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- 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
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- 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
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
Abstract
Description
測定装置:高速GPC装置(東ソー株式会社製「HLC−8220GPC」)
カラム:東ソー株式会社製の下記のカラムを直列に接続して使用した。
「TSKgel G5000」(7.8mmI.D.×30cm)×1本
「TSKgel G4000」(7.8mmI.D.×30cm)×1本
「TSKgel G3000」(7.8mmI.D.×30cm)×1本
「TSKgel G2000」(7.8mmI.D.×30cm)×1本
検出器:RI(示差屈折計)
カラム温度:40℃
溶離液:テトラヒドロフラン(THF)
流速:1.0mL/分
注入量:100μL(試料濃度4mg/mLのテトラヒドロフラン溶液)
標準試料:下記の単分散ポリスチレンを用いて検量線を作成した。
東ソー株式会社製「TSKgel 標準ポリスチレン A−500」
東ソー株式会社製「TSKgel 標準ポリスチレン A−1000」
東ソー株式会社製「TSKgel 標準ポリスチレン A−2500」
東ソー株式会社製「TSKgel 標準ポリスチレン A−5000」
東ソー株式会社製「TSKgel 標準ポリスチレン F−1」
東ソー株式会社製「TSKgel 標準ポリスチレン F−2」
東ソー株式会社製「TSKgel 標準ポリスチレン F−4」
東ソー株式会社製「TSKgel 標準ポリスチレン F−10」
東ソー株式会社製「TSKgel 標準ポリスチレン F−20」
東ソー株式会社製「TSKgel 標準ポリスチレン F−40」
東ソー株式会社製「TSKgel 標準ポリスチレン F−80」
東ソー株式会社製「TSKgel 標準ポリスチレン F−128」
東ソー株式会社製「TSKgel 標準ポリスチレン F−288」
東ソー株式会社製「TSKgel 標準ポリスチレン F−550」
測定装置:高速GPC装置(東ソー株式会社製「HLC−8220GPC」)
カラム:東ソー株式会社製の下記のカラムを直列に接続して使用した。
「TSKgel G5000」(7.8mmI.D.×30cm)×1本
「TSKgel G4000」(7.8mmI.D.×30cm)×1本
「TSKgel G3000」(7.8mmI.D.×30cm)×1本
「TSKgel G2000」(7.8mmI.D.×30cm)×1本
検出器:RI(示差屈折計)
カラム温度:40℃
溶離液:テトラヒドロフラン(THF)
流速:1.0mL/分
注入量:100μL(試料濃度4mg/mLのテトラヒドロフラン溶液)
標準試料:下記の単分散ポリスチレンを用いて検量線を作成した。
東ソー株式会社製「TSKgel 標準ポリスチレン A−500」
東ソー株式会社製「TSKgel 標準ポリスチレン A−1000」
東ソー株式会社製「TSKgel 標準ポリスチレン A−2500」
東ソー株式会社製「TSKgel 標準ポリスチレン A−5000」
東ソー株式会社製「TSKgel 標準ポリスチレン F−1」
東ソー株式会社製「TSKgel 標準ポリスチレン F−2」
東ソー株式会社製「TSKgel 標準ポリスチレン F−4」
東ソー株式会社製「TSKgel 標準ポリスチレン F−10」
東ソー株式会社製「TSKgel 標準ポリスチレン F−20」
東ソー株式会社製「TSKgel 標準ポリスチレン F−40」
東ソー株式会社製「TSKgel 標準ポリスチレン F−80」
東ソー株式会社製「TSKgel 標準ポリスチレン F−128」
東ソー株式会社製「TSKgel 標準ポリスチレン F−288」
東ソー株式会社製「TSKgel 標準ポリスチレン F−550」
攪拌機、温度計、冷却管及び窒素導入管を備えた4つ口のフラスコに、ジエチレングリコールジメチルエーテル340gを仕込み、窒素気流下に110℃に昇温した後、メトキシポリエチレングリコールアクリレート(1分子当たりのオキシエチレン単位数:平均13;以下、「13EOA」と略記する。)325g、2−ヒドロキシエチルメタクリレート(以下、「HEMA」と略記する。)45g、n−ブチルアクリレート(以下、「BA」と略記する。)280g、及びt−ブチルパーオキシ−2−エチルヘキサノエート10gからなる混合液を5時間かけて滴下した。滴下後、110℃で9時間反応して、重量平均分子量が12,000であり、水酸基価が30である重合体の溶液(樹脂分65質量%)を得た。以下、この重合体を重合体(A−1)と略記する。
攪拌機、温度計、冷却管及び窒素導入管を備えた4つ口のフラスコに、ジエチレングリコールジメチルエーテル340gを仕込み、窒素気流下に110℃に昇温した後、13EOA325g、HEMA91g、イソボルニルアクリレート(以下、「IBA」と略記する。)234g、及びt−ブチルパーオキシ−2−エチルヘキサノエート10gからなる混合液を5時間かけて滴下した。滴下後、110℃で9時間反応して、重量平均分子量が15,000であり、水酸基価が60である重合体の溶液(樹脂分65質量%)を得た。以下、この重合体を重合体(A−2)と略記する。
攪拌機、温度計、冷却管及び窒素導入管を備えた4つ口のフラスコに、ジエチレングリコールジメチルエーテル340gを仕込み、窒素気流下に110℃に昇温した後、メトキシポリエチレングリコールメタクリレート(1分子当たりのオキシエチレン単位数:平均9:以下、「9EOMA」と略記する。)423g、HEMA45g、n−ブチルメタクリレート(以下、「BMA」と略記する。)201g、及びt−ブチルパーオキシ−2−エチルヘキサノエート10gからなる混合液を5時間かけて滴下した。滴下後、110℃で9時間反応して、重量平均分子量が14,000であり、水酸基価が17である重合体の溶液(樹脂分65質量%)を得た。以下、この重合体を重合体(A−3)と略記する。
攪拌機、温度計、冷却管及び窒素導入管を備えた4つ口のフラスコに、ジプロピレングリコールジメチルエーテル340gを仕込み、窒素気流下に110℃に昇温した後、13EOA130g、メトキシポリエチレングリコールアクリレート(1分子当たりのオキシエチレン単位数:平均23;以下、「23EOA」と略記する。)130g、2−ヒドロキシエチルアクリレート(以下、「HEA」と略記する。)45g、シクロヘキシルメタクリレート(以下、「CHMA」と略記する。)280g、及びt−ブチルパーオキシ−2−エチルヘキサノエート10gからなる混合液を5時間かけて滴下した。滴下後、110℃で9時間反応して、重量平均分子量が16,000であり、水酸基価が30である重合体の溶液(樹脂分65質量%)を得た。以下、この重合体を重合体(A−4)と略記する。
攪拌機、温度計、冷却管及び窒素導入管を備えた4つ口のフラスコに、ジエチレングリコールジメチルエーテル340gを仕込み、窒素気流下に110℃に昇温した後、13EOA325g、BA325g、及びt−ブチルパーオキシ−2−エチルヘキサノエート10gからなる混合液を5時間かけて滴下した。滴下後、110℃で9時間反応して、重量平均分子量が10,000である重合体の溶液(樹脂分65質量%)を得た。以下、この重合体を重合体(RA−1)と略記する。
攪拌機、温度計、冷却管及び窒素導入管を備えた4つ口のフラスコに、ジエチレングリコールジメチルエーテル340g、ω−カルボキシ−ポリカプロラクトンモノアクリレート(東亞合成株式会社製「アロニックス M5300」;以下、「clA」と略記する。)13gを仕込み、窒素気流下に110℃に昇温した後、HEMA39g、メチルメタクリレート(以下、「MMA」と略記する。)390g、BA130g、アクリル酸(以下、「AA」と略記する。)78g、及びt−ブチルパーオキシ−2−エチルヘキサノエート9gからなる混合液を5時間かけて滴下した。滴下後、110℃で9時間反応して、重量平均分子量が35,000であり、酸価が97である重合体の溶液(樹脂分65質量%)を得た。以下、この重合体を重合体(RA−2)と略記する。
攪拌機、温度計及び冷却管を備えた4つ口フラスコに、ヘキサメチレンジイソシアネート104g、メトキノン0.2g、及びジブチル錫ジラウレート0.2gを仕込み、撹拌を開始し60℃に昇温した。同温度で、ペンタエリスリトールトリアクリレート(以下、「PETA」と略記する。)及びペンタエリスリトールテトラアクリレートの混合物(東亞合成株式会社製「アロニックス M305」、ペンタエリスリトールトリアクリレート比率:60質量%、水酸基価:115;以下、「PETA混合物」と略記する。)645gを10回に分けて10分毎に仕込んだ。さらに5時間反応を継続して赤外線スペクトルで2250cm−1のイソシアネート基の吸収が消失したことを確認して反応を終了し、ウレタンアクリレートとペンタエリスリトールテトラアクリレートとの混合物であるウレタンアクリレート組成物(RB−1)を得た。
攪拌機、温度計及び冷却管を備えた4つ口フラスコに、合成例1で得られた重合体(A−1)の65質量%溶液615g(重合体(A−1)として400g)、メトキノン0.2g、ジブチル錫ジラウレート0.2g、PETA混合物472g、及び4,4’−ジシクロヘキシルメタンジイソシアネート(以下、「H12MDI」と略記する。)128gを仕込み、80℃まで昇温した後、同温度で5時間撹拌混合し、赤外線スペクトルで2250cm−1のイソシアネート基の吸収が消失したことを確認して反応を終了した。次いで、得られた反応物とイオン交換水1,285gとを混合し、さらに光重合開始剤(BASFジャパン株式会社製「イルガキュア500」、1−ヒドロキシシクロヘキシルフェニルケトンとベンゾフェノンとのモル比1:1の共融混合物)40gを混合して、活性エネルギー線硬化型水性樹脂組成物(W−1)を得た。
攪拌機、温度計及び冷却管を備えた4つ口フラスコに、PETA混合物563g、H12MDI 187g、メトキノン0.2g、及びジブチル錫ジラウレート0.2gを仕込み、80℃まで昇温し、同温度で2時間撹拌混合した後、合成例2で得られた重合体(A−2)の65質量%溶液385g(重合体(A−2)として250g)を加えた。同温度でさらに4時間撹拌混合し、赤外線スペクトルで2250cm−1のイソシアネート基の吸収が消失したことを確認して反応を終了した。次いで、得られた反応物とイオン交換水1,365gとを混合し、さらに光重合開始剤(BASFジャパン株式会社製「イルガキュア500」、1−ヒドロキシシクロヘキシルフェニルケトンとベンゾフェノンとのモル比1:1の共融混合物)40gを混合して、活性エネルギー線硬化型水性樹脂組成物(W−2)を得た。
攪拌機、温度計及び冷却管を備えた4つ口フラスコに、PETA混合物563g、イソホロンジイソシアネート(以下、「IPDI」と略記する。)183g、メトキノン0.2g、及びジブチル錫ジラウレート0.2gを仕込み、80℃まで昇温し、同温度で2時間撹拌混合した後、合成例2で得られた重合体(A−2)の65質量%溶液567g(重合体(A−2)として369g)を加えた。同温度でさらに4時間撹拌混合し、赤外線スペクトルで2250cm−1のイソシアネート基の吸収が消失したことを確認して反応を終了した。次いで、得られた反応物とイオン交換水1,365gとを混合し、さらに光重合開始剤(BASFジャパン株式会社製「イルガキュア500」、1−ヒドロキシシクロヘキシルフェニルケトンとベンゾフェノンとのモル比1:1の共融混合物)40gを混合して、活性エネルギー線硬化型水性樹脂組成物(W−2)を得た。
攪拌機、温度計及び冷却管を備えた4つ口フラスコに、合成例3で得られた重合体(A−3)の65質量%溶液385g(重合体(A−3)として250g)、メトキノン0.2g、ジブチル錫ジラウレート0.2g、PETA混合物610g、及びIPDI 140gを仕込み、80℃まで昇温した後、同温度で5時間撹拌混合し、赤外線スペクトルで2250cm−1のイソシアネート基の吸収が消失したことを確認して反応を終了した。次いで、得られた反応物とイオン交換水1,365gとを混合し、さらに光重合開始剤(BASFジャパン株式会社製「イルガキュア500」、1−ヒドロキシシクロヘキシルフェニルケトンとベンゾフェノンとのモル比1:1の共融混合物)40gを混合して、活性エネルギー線硬化型水性樹脂組成物(W−4)を得た。
攪拌機、温度計及び冷却管を備えた4つ口フラスコに、合成例3で得られた重合体重合体(A−4)の65質量%溶液769g(重合体(A−4)として500g)、メトキノン0.2g、ジブチル錫ジラウレート0.2g、PETA混合物426g、及びヘキサメチレンジイソシアネート(以下、「HDI」と略記する。)74gを仕込み、80℃まで昇温した後、同温度で5時間撹拌混合し、赤外線スペクトルで2250cm−1のイソシアネート基の吸収が消失したことを確認して反応を終了した。次いで、得られた反応物とイオン交換水1,305gとを混合し、さらに光重合開始剤(BASFジャパン株式会社製「イルガキュア500」、1−ヒドロキシシクロヘキシルフェニルケトンとベンゾフェノンとのモル比1:1の共融混合物)40gを混合して、活性エネルギー線硬化型水性樹脂組成物(W−5)を得た。
攪拌機、温度計及び冷却管を備えた4つ口フラスコに、合成例5で得られた重合体(RA−1)の65質量%溶液615g(重合体(RA−1)として400g)、メトキノン0.2g、ジブチル錫ジラウレート0.2g、PETA混合物493g、及びH12MDI 107gを仕込み、80℃まで昇温した後、同温度で5時間撹拌混合し、赤外線スペクトルで2250cm−1のイソシアネート基の吸収が消失したことを確認して反応を終了した。次いで、得られた反応物とイオン交換水1,285gとを混合し、さらに光重合開始剤(BASFジャパン株式会社製「イルガキュア500」、1−ヒドロキシシクロヘキシルフェニルケトンとベンゾフェノンとのモル比1:1の共融混合物)40gを混合して、活性エネルギー線硬化型水性樹脂組成物(RW−1)を得た。
攪拌機、温度計及び冷却管を備えた4つ口フラスコに、合成例6で得られた重合体(RA−2)の65質量%溶液442g(重合体(RA−2)として287g)、合成例7で得られたウレタンアクリレート組成物(RB−1)500g、PETA混合物200gを仕込み、70℃で加温攪拌しながらトリエチルアミン40gを加えて攪拌混合した。次いで、イオン交換水1,379gを10回に分割投入し、さらに光重合開始剤(BASFジャパン株式会社製「イルガキュア500」、1−ヒドロキシシクロヘキシルフェニルケトンとベンゾフェノンとのモル比1:1の共融混合物)40gを混合して、活性エネルギー線硬化型水性樹脂組成物(RW−2)を得た。
実施例1で得られた活性エネルギー線硬化型水性樹脂組成物(W−1)を用いて、活性エネルギー線硬化型水性塗料としての性能を評価するため、貯蔵安定性、硬化塗膜の外観及び表面硬度(鉛筆硬度)を評価した。
活性エネルギー線硬化型水性樹脂組成物(W−1)を200mlのガラス容器に密封して40℃で静置保存し、成分分離の状況を目視で観察して、下記の基準にしたがって、貯蔵安定性を評価した。
○:6か月間以上分離沈降なし。
△:2か月以上6か月未満で分離沈降あり。
×:2か月未満で分離沈降あり。
ガラス板、ABS(アクリロニトリル−ブタジエン−スチレン共重合体)板上に、乾燥後の膜厚が10μmになるように活性エネルギー線硬化型水性樹脂組成物(W−1)をスプレー塗装して、乾燥機中で60℃の温度で10分間の予備乾燥をした後、出力80W/cmの高圧水銀ランプを用いて、照射量0.8J/cm2の紫外線照射を行い、評価用硬化塗膜を作製した。
上記で得られた評価用硬化塗膜の外観を目視で観察し、下記の基準にしたがって、硬化塗膜外観を評価した。
○:硬化塗膜が透明である。
△:硬化塗膜がわずかに白化している。
×:硬化塗膜が白化している。
ABS板上の硬化塗膜に、カッターにて1mm角で10×10個の切れ目を入れ、セロファンテープによる剥離試験を行い、残存する目数を下記の基準にしたがって、塗膜密着性を評価した。また、硬化塗膜を基材のABS板とともに80℃の温水に2時間浸漬した後、取り出して25℃で2時間乾燥した。その後、同様にセロファンテープによる剥離試験を行い、残存する目数を下記の基準にしたがって、温水浸漬後の塗膜密着性を評価した。
○:95〜100個
△:60〜94個
×:59個以下
上記で得られた評価用硬化塗膜の表面について、JIS S 6006:2007に規定された鉛筆を用いて、JIS K 5600−5−4:1999に準じて、傷跡を生じなかった最も硬い鉛筆の硬度を鉛筆硬度として測定した。
実施例6で用いた活性エネルギー線硬化型水性樹脂組成物(W−1)に代えて、実施例2〜5で得られた活性エネルギー線硬化型水性樹脂組成物(W−2)〜(W−5)をそれぞれ用いた以外は実施例6と同様に操作して、活性エネルギー線硬化型水性塗料としての性能として、貯蔵安定性、硬化塗膜の外観及び表面硬度(鉛筆硬度)を評価した。
実施例6で用いた活性エネルギー線硬化型水性樹脂組成物(W−1)に代えて、比較例1〜2で得られた活性エネルギー線硬化型水性樹脂組成物(RW−1)〜(RW−2)をそれぞれ用いた以外は実施例6と同様に操作して、活性エネルギー線硬化型水性塗料としての性能として、貯蔵安定性、硬化塗膜の外観及び表面硬度(鉛筆硬度)を評価した。
Claims (7)
- ポリオキシアルキレン基を有するアクリル単量体(a1)、前記アクリル単量体(a1)以外の水酸基を有するアクリル単量体(a2)、並びに前記アクリル単量体(a1)及びアクリル単量体(a2)以外のアクリル単量体(a3)を必須原料として共重合して得られたアクリル樹脂(A)と、ポリイソシアネート化合物(B)と、水酸基を有する(メタ)アクリレート(C)とを反応させ、その反応物を水媒体中で分散させることで得られる活性エネルギー線硬化型水性樹脂組成物であって、前記アクリル樹脂(A)の原料である単量体成分中の前記アクリル単量体(a1)の質量比率が30〜80質量%の範囲であり、前記アクリル単量体(a2)の質量比率が2〜30質量%の範囲であることを特徴とする活性エネルギー線硬化型水性樹脂組成物。
- 前記ポリオキシアルキレン基が、ポリオキシエチレン基である請求項1記載の活性エネルギー線硬化型水性樹脂組成物。
- 前記ポリイソシアネート化合物(B)が、脂肪族ジイソシアネート化合物又は脂環式ジイソシアネート化合物である請求項1又は2記載の活性エネルギー線硬化型水性樹脂組成物。
- 前記(メタ)アクリレート(C)が、ペンタエリスリトールトリアクリレートである請求項1〜3のいずれか1項記載の活性エネルギー線硬化型水性樹脂組成物。
- 前記アクリル単量体(a3)が、脂環式アクリル単量体である請求項1〜4のいずれか1項記載の活性エネルギー線硬化型水性樹脂組成物。
- 請求項1〜5のいずれか1項記載の活性エネルギー線硬化型水性樹脂組成物を含有することを特徴とする活性エネルギー線硬化型水性塗料。
- 請求項6記載の活性エネルギー線硬化型水性塗料が塗装されたことを特徴とする物品。
Priority Applications (1)
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KR101924553B1 (ko) * | 2015-09-15 | 2018-12-03 | 케이제이 케미칼즈 가부시키가이샤 | 우레탄변성 (메타)아크릴아미드 화합물 및 이를 함유하는 활성에너지선 경화성 수지 조성물 |
CN105131801B (zh) * | 2015-09-23 | 2018-03-30 | 上海贻赛新材料科技有限公司 | 一种水性聚氨酯涂料及其制备方法 |
CN105111912B (zh) * | 2015-10-08 | 2017-09-01 | 杨年富 | Uv水性光固化涂料 |
JP2019073618A (ja) * | 2017-10-16 | 2019-05-16 | Dic株式会社 | 積層体 |
WO2019220663A1 (ja) * | 2018-05-15 | 2019-11-21 | 日立化成株式会社 | 樹脂組成物、蓄熱材、及び物品 |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6284113A (ja) * | 1985-10-09 | 1987-04-17 | Nippon Paint Co Ltd | 反応性微小樹脂粒子、その製法ならびに硬化組成物 |
JPH03250014A (ja) * | 1990-02-28 | 1991-11-07 | Mitsubishi Kasei Corp | 親水性ポリウレタン |
JPH05301935A (ja) * | 1992-04-28 | 1993-11-16 | Sekisui Chem Co Ltd | 光硬化型樹脂組成物 |
WO2002032977A1 (fr) * | 2000-10-20 | 2002-04-25 | Dainippon Ink And Chemicals, Inc. | Composition de polyisocyanate dispersable dans l"eau, son procede de production, composition durcissable a base d"eau et son application |
JP2002216845A (ja) * | 2001-01-18 | 2002-08-02 | Nippon Synthetic Chem Ind Co Ltd:The | 高分子固体電解質及びそれを用いた電気化学素子、二次電池 |
JP2003064149A (ja) * | 2001-08-30 | 2003-03-05 | Dainippon Ink & Chem Inc | 水分散性ポリイソシアネート組成物、水性硬化性組成物、水性硬化性組成物を含む水性塗料および水性接着剤 |
JP2004244435A (ja) * | 2003-02-10 | 2004-09-02 | Mitsubishi Chemicals Corp | 樹脂組成物水性エマルション及びそれを用いてなる表面被覆剤 |
JP2008156659A (ja) * | 2008-02-12 | 2008-07-10 | Dainippon Printing Co Ltd | 光硬化性樹脂、及び光硬化性樹脂組成物 |
JP2009051984A (ja) * | 2007-08-29 | 2009-03-12 | Toyo Ink Mfg Co Ltd | 制電性アクリル系樹脂組成物 |
JP2012025807A (ja) * | 2010-07-21 | 2012-02-09 | Nippon Synthetic Chem Ind Co Ltd:The | アクリル系粘着剤、粘着シート、アクリル系樹脂組成物 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5311314B2 (ja) * | 1974-09-25 | 1978-04-20 | ||
US4108840A (en) * | 1977-04-15 | 1978-08-22 | Ppg Industries, Inc. | Urea-urethane-acrylate radiation curable coating compositions and methods of making same |
JP3103679B2 (ja) * | 1991-08-19 | 2000-10-30 | アーチ ケミカルズ,インコーポレイテッド | ポリマーポリオールの製造において分散安定剤として有用な変成ポリウレタンオリゴマー |
DE69916750T2 (de) * | 1998-11-17 | 2005-01-05 | Showa Denko K.K. | Photohärtbare Zusammensetzung |
JP2000212234A (ja) | 1998-11-17 | 2000-08-02 | Showa Denko Kk | 光硬化性組成物 |
US6270905B1 (en) * | 1999-02-16 | 2001-08-07 | Ppg Industries Ohio, Inc. | Multi-component composite coating composition and coated substrate |
JP2002270235A (ja) * | 2001-03-07 | 2002-09-20 | Nisshinbo Ind Inc | 高分子ゲル電解質用プレゲル組成物及びその脱水方法並びに二次電池及び電気二重層キャパシタ |
JP2004010779A (ja) | 2002-06-07 | 2004-01-15 | Nippon Paint Co Ltd | 紫外線硬化型水性塗料組成物 |
DE102005004639A1 (de) | 2005-02-01 | 2006-08-03 | Ashland-Südchemie-Kernfest GmbH | Modifiziertes Poly(meth)acrylat mit reaktiven ethylenischen Gruppen und dessen Verwendung |
JP4837313B2 (ja) * | 2005-06-22 | 2011-12-14 | 日本ペイント株式会社 | 水性クリヤー塗料組成物及びクリヤー塗膜形成方法 |
CN100424145C (zh) * | 2006-05-15 | 2008-10-08 | 汕头大学 | 紫外光固化水性聚氨酯丙烯酸酯涂料树脂及其制备方法 |
US20100010162A1 (en) | 2006-11-09 | 2010-01-14 | Dic Corporation | Active energy-ray-curable water- based resin composition, active energy-ray-curable coating material, method of forming cured coating film, and article |
CN101629050B (zh) * | 2009-06-30 | 2012-01-18 | 广东华润涂料有限公司 | 一种聚氨酯丙烯酸酯型水性uv涂料及其制作方法 |
CN102844346B (zh) * | 2010-03-31 | 2014-10-15 | Dic株式会社 | 活性能量射线固化型树脂组合物、其固化物及薄膜 |
JP5480930B2 (ja) * | 2011-03-31 | 2014-04-23 | ダイキン工業株式会社 | 含フッ素共重合体を含有する組成物 |
-
2013
- 2013-01-10 EP EP13738337.8A patent/EP2805978A4/en not_active Withdrawn
- 2013-01-10 CN CN201380005268.8A patent/CN104039861B/zh active Active
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- 2013-01-10 KR KR1020147013315A patent/KR101624213B1/ko active IP Right Grant
- 2013-01-10 WO PCT/JP2013/050291 patent/WO2013108707A1/ja active Application Filing
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Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6284113A (ja) * | 1985-10-09 | 1987-04-17 | Nippon Paint Co Ltd | 反応性微小樹脂粒子、その製法ならびに硬化組成物 |
JPH03250014A (ja) * | 1990-02-28 | 1991-11-07 | Mitsubishi Kasei Corp | 親水性ポリウレタン |
JPH05301935A (ja) * | 1992-04-28 | 1993-11-16 | Sekisui Chem Co Ltd | 光硬化型樹脂組成物 |
WO2002032977A1 (fr) * | 2000-10-20 | 2002-04-25 | Dainippon Ink And Chemicals, Inc. | Composition de polyisocyanate dispersable dans l"eau, son procede de production, composition durcissable a base d"eau et son application |
JP2002216845A (ja) * | 2001-01-18 | 2002-08-02 | Nippon Synthetic Chem Ind Co Ltd:The | 高分子固体電解質及びそれを用いた電気化学素子、二次電池 |
JP2003064149A (ja) * | 2001-08-30 | 2003-03-05 | Dainippon Ink & Chem Inc | 水分散性ポリイソシアネート組成物、水性硬化性組成物、水性硬化性組成物を含む水性塗料および水性接着剤 |
JP2004244435A (ja) * | 2003-02-10 | 2004-09-02 | Mitsubishi Chemicals Corp | 樹脂組成物水性エマルション及びそれを用いてなる表面被覆剤 |
JP2009051984A (ja) * | 2007-08-29 | 2009-03-12 | Toyo Ink Mfg Co Ltd | 制電性アクリル系樹脂組成物 |
JP2008156659A (ja) * | 2008-02-12 | 2008-07-10 | Dainippon Printing Co Ltd | 光硬化性樹脂、及び光硬化性樹脂組成物 |
JP2012025807A (ja) * | 2010-07-21 | 2012-02-09 | Nippon Synthetic Chem Ind Co Ltd:The | アクリル系粘着剤、粘着シート、アクリル系樹脂組成物 |
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CN104039861A (zh) | 2014-09-10 |
EP2805978A1 (en) | 2014-11-26 |
US20140309360A1 (en) | 2014-10-16 |
TW201335210A (zh) | 2013-09-01 |
US9605174B2 (en) | 2017-03-28 |
KR20140085521A (ko) | 2014-07-07 |
JPWO2013108707A1 (ja) | 2015-05-11 |
WO2013108707A1 (ja) | 2013-07-25 |
EP2805978A4 (en) | 2015-08-19 |
TWI595016B (zh) | 2017-08-11 |
CN104039861B (zh) | 2016-08-17 |
KR101624213B1 (ko) | 2016-05-25 |
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