JP5472544B2 - 活性エネルギー線硬化型樹脂組成物、その製造方法、塗料、塗膜、及びフィルム - Google Patents
活性エネルギー線硬化型樹脂組成物、その製造方法、塗料、塗膜、及びフィルム Download PDFInfo
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- JP5472544B2 JP5472544B2 JP2013530268A JP2013530268A JP5472544B2 JP 5472544 B2 JP5472544 B2 JP 5472544B2 JP 2013530268 A JP2013530268 A JP 2013530268A JP 2013530268 A JP2013530268 A JP 2013530268A JP 5472544 B2 JP5472544 B2 JP 5472544B2
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- 239000011248 coating agent Substances 0.000 title claims description 119
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- 150000001875 compounds Chemical class 0.000 claims description 131
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 117
- 239000010419 fine particle Substances 0.000 claims description 112
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- 238000000034 method Methods 0.000 claims description 70
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 61
- 239000002245 particle Substances 0.000 claims description 44
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- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 12
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- 125000004432 carbon atom Chemical group C* 0.000 description 10
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 9
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- 239000000654 additive Substances 0.000 description 9
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
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- 239000003960 organic solvent Substances 0.000 description 9
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 8
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- 229910052757 nitrogen Inorganic materials 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 6
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- 239000011247 coating layer Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 6
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- 238000002360 preparation method Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
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- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 4
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 4
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- JYSWMLAADBQAQX-UHFFFAOYSA-N 2-prop-2-enoyloxyacetic acid Chemical compound OC(=O)COC(=O)C=C JYSWMLAADBQAQX-UHFFFAOYSA-N 0.000 description 4
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- TUOBEAZXHLTYLF-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CC)COC(=O)C=C TUOBEAZXHLTYLF-UHFFFAOYSA-N 0.000 description 4
- 125000005396 acrylic acid ester group Chemical group 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- FAIDIRVMPHBRLT-UHFFFAOYSA-N propane-1,2,3-triol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OCC(O)CO FAIDIRVMPHBRLT-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- RKYJPYDJNQXILT-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxycarbonyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCCOC(=O)C=C RKYJPYDJNQXILT-UHFFFAOYSA-N 0.000 description 3
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- 230000008719 thickening Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- HKFSBKQQYCMCKO-UHFFFAOYSA-N trichloro(prop-2-enyl)silane Chemical compound Cl[Si](Cl)(Cl)CC=C HKFSBKQQYCMCKO-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 150000007964 xanthones Chemical class 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
- 239000004711 α-olefin Substances 0.000 description 1
Images
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- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side 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
- C09D133/06—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
- C09D133/08—Homopolymers or copolymers of acrylic acid esters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
- B32B27/20—Layered products comprising a layer of synthetic resin characterised by the use of special additives using fillers, pigments, thixotroping agents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
- B32B27/308—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising acrylic (co)polymers
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- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/12—Polymers provided for in subclasses C08C or C08F
- C08F290/126—Polymers of unsaturated carboxylic acids or derivatives thereof
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- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
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- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
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- 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
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/66—Additives characterised by particle size
- C09D7/68—Particle size between 100-1000 nm
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- C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
- C08J2301/08—Cellulose derivatives
- C08J2301/10—Esters of organic acids
- C08J2301/12—Cellulose acetate
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- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2333/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
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- C08J2333/12—Homopolymers or copolymers of methyl methacrylate
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- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
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- C08J2433/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
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Description
カラム ; 東ソー株式会社製ガードカラムHXL−H
+東ソー株式会社製 TSKgel G5000HXL
+東ソー株式会社製 TSKgel G4000HXL
+東ソー株式会社製 TSKgel G3000HXL
+東ソー株式会社製 TSKgel G2000HXL
検出器 ; RI(示差屈折計)
データ処理:東ソー株式会社製 SC−8010
測定条件: カラム温度 40℃
溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 ;ポリスチレン
試料 ;樹脂固形分換算で0.4重量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
前記アクリル重合体(X1)の原料となる前記アクリル重合体(Y1)は、前記エポキシ基と(メタ)アクリロイル基とを有する化合物(y1)の単独重合体でも良いし、他の重合性化合物(v1)との共重合体でも良い。
前記アクリル重合体(X2)の原料となる前記アクリル重合体(Y2)は、前記カルボキシル基と(メタ)アクリロイル基とを有する化合物(y2)の単独重合体でも良いし、他の重合性化合物(v2)との共重合体でも良い。
前記アクリル重合体(X3)の原料となる前記アクリル重合体(Y3)は、前記水酸基と(メタ)アクリロイル基とを有する化合物(y3)の単独重合体でも良いし、他の重合性化合物(v3)との共重合体でも良い。
カラム ; 東ソー株式会社製ガードカラムHXL−H
+東ソー株式会社製 TSKgel G5000HXL
+東ソー株式会社製 TSKgel G4000HXL
+東ソー株式会社製 TSKgel G3000HXL
+東ソー株式会社製 TSKgel G2000HXL
検出器 ; RI(示差屈折計)
データ処理:東ソー株式会社製 SC−8010
測定条件: カラム温度 40℃
溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 ;ポリスチレン
試料 ;樹脂固形分換算で0.4重量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
・無機微粒子(a−1):日本アエロジル株式会社製「アエロジルR7200」一次平均粒子径が12nmであり、粒子表面に(メタ)アクリロイル基を有するシリカ微粒子
・無機微粒子(a−2):日本アエロジル株式会社製「アエロジルR711」一次平均粒子径が12nmであり、粒子表面に(メタ)アクリロイル基を有するシリカ微粒子
・無機微粒子(a−3):日本アエロジル社株式会社製「アエロジルOX50」(一次平均粒子径が40nmのシリカ微粒子)100部、水4部及び3−トリメキシシリル−プロピルメタクリレート18部を混合し、140℃で熱処理して得たシリカ微粒子
・無機微粒子(a−4):日本アエロジル株式会社製「アエロジル90G」(一次平均粒子径が20nmのシリカ微粒子)100部、水4部及び3−トリメキシシリル−プロピルメタクリレート18部を混合し、140℃で熱処理して得たシリカ微粒子
・無機微粒子(a−5):日本アエロジル株式会社製「アエロジル50」一次平均粒子径が30nmであり、粒子表面に修飾基を持たないシリカ微粒子
・無機微粒子(a−6):日産化学株式会社製「MEK−ST」
・無機微粒子(a−7):日揮触媒化製株式会社製「ELCOM V−8804」粒子表面に(メタ)アクリロイル基を有するシリカ微粒子
・無機微粒子(a−8):日本アエロジル株式会社製「アエロジル974」一次平均粒子径が12nmであり、粒子表面にメチル基を有するシリカ微粒子
・無機微粒子(a−9):昭和電工株式会社製「UFA−150」一次平均粒子径15nmのアルミナ微粒子
アクリル重合体(X−1)の製造
撹拌装置、冷却管、滴下ロートおよび窒素導入管を備えた反応装置に、プロピレングリコールモノメチルエーテル480質量部を仕込み、撹拌しながら系内温度が110℃になるまで昇温し、次いで、グリシジルメタアクリレート91質量部、メチルメタアクリレート318質量部、シクロヘキサンメタアクリレート45質量部およびt−ブチルパーオキシ−2−エチルヘキサノエート(日本乳化剤株式会社製「パーブチルO」)15質量部からなる混合液を3時間かけて滴下ロートより滴下した後、110℃で15時間保持した。次いで、90℃まで降温した後、メトキノン0.1質量部およびアクリル酸46質量部を仕込んだ後、トリフェニルホスフィン5質量部を添加後、さらに100℃まで昇温して8時間保持し、アクリル重合体(X−1)のプロピレングリコールモノメチルエーテル溶液1000質量部(不揮発分50.0質量%)を得た。該アクリル重合体(X−1)の各性状値は以下の通り。重量平均分子量(Mw):24,000、固形分換算の理論アクリロイル基当量:747g/eq、水酸基価75mgKOH/g
アクリル重合体(X−2)の製造
撹拌装置、冷却管、滴下ロートおよび窒素導入管を備えた反応装置に、メチルイソブチルケトン480質量部を仕込み、撹拌しながら系内温度が110℃になるまで昇温し、次いで、グリシジルメタアクリレート130質量部、メチルメタアクリレート304質量部およびt−ブチルパーオキシ−2−エチルヘキサノエート(日本乳化剤株式会社製「パーブチルO」)15質量部からなる混合液を3時間かけて滴下ロートより滴下した後、110℃で15時間保持した。次いで、90℃まで降温した後、メトキノン0.1質量部およびアクリル酸66質量部を仕込んだ後、トリフェニルホスフィン5質量部を添加後、さらに100℃まで昇温して8時間保持し、アクリル重合体(X−2)のメチルイソブチルケトン溶液1000質量部(不揮発分50.0質量%)を得た。該アクリル重合体(X−2)の各性状値は以下の通り。重量平均分子量(Mw):26,000、固形分換算の理論アクリロイル基当量:522g/eq、水酸基価108mgKOH/g
アクリル重合体(X−3)の製造
撹拌装置、冷却管、滴下ロートおよび窒素導入管を備えた反応装置に、プロピレングリコールモノメチルエーテル455質量部を仕込み、撹拌しながら系内温度が110℃になるまで昇温し、次いで、グリシジルメタアクリレート166質量部、メチルメタアクリレート208質量部、イソボロニルメタアクリレート42質量部、およびt−ブチルパーオキシ−2−エチルヘキサノエート(日本乳化剤株式会社製「パーブチルO」)40質量部からなる混合液を3時間かけて滴下ロートより滴下した後、110℃で15時間保持した。次いで、90℃まで降温した後、メトキノン0.1質量部およびアクリル酸84質量部を仕込んだ後、トリフェニルホスフィン5質量部を添加後、さらに100℃まで昇温して8時間保持し、アクリル重合体(X−3)のプロピレングリコールモノメチルエーテル溶液1000質量部(不揮発分50.0質量%)を得た。該アクリル重合体(X−3)の各性状値は以下の通り。重量平均分子量(Mw):11,000、固形分換算の理論アクリロイル基当量:409g/eq、水酸基価137mgKOH/g
アクリル重合体(X−4)の製造
撹拌装置、冷却管、滴下ロートおよび窒素導入管を備えた反応装置に、メチルイソブチルケトン485質量部を仕込み、撹拌しながら系内温度が110℃になるまで昇温し、次いで、グリシジルメタアクリレート230質量部、メチルメタアクリレート115質量部、シクロヘキサンメタアクリレート38質量部、およびt−ブチルパーオキシ−2−エチルヘキサノエート(日本乳化剤株式会社製「パーブチルO」)10質量部からなる混合液を3時間かけて滴下ロートより滴下した後、110℃で15時間保持した。次いで、90℃まで降温した後、メトキノン0.1質量部およびアクリル酸117質量部を仕込んだ後、トリフェニルホスフィン5質量部を添加後、さらに100℃まで昇温して8時間保持し、アクリル重合体(X−4)のメチルイソブチルケトン溶液1000質量部(不揮発分50.0質量%)を得た。該アクリル重合体(X−4)の各性状値は以下の通り。重量平均分子量(Mw):42,000、固形分換算の理論アクリロイル基当量:297g/eq、水酸基価189mgKOH/g
アクリル重合体(X−5)の製造
撹拌装置、冷却管、滴下ロートおよび窒素導入管を備えた反応装置に、メチルイソブチルケトン470質量部を仕込み、撹拌しながら系内温度が110℃になるまで昇温し、次いで、グリシジルメタアクリレート321質量部、メチルメタアクリレート17質量部およびt−ブチルパーオキシ−2−エチルヘキサノエート(日本乳化剤株式会社製「パーブチルO」)25質量部からなる混合液を3時間かけて滴下ロートより滴下した後、110℃で15時間保持した。次いで、90℃まで降温した後、メトキノン0.1質量部およびアクリル酸163質量部を仕込んだ後、トリフェニルホスフィン5質量部を添加後、さらに100℃まで昇温して8時間保持し、アクリル重合体(X−5)のメチルイソブチルケトン溶液1000質量部(不揮発分50.0質量%)を得た。該アクリル重合体(X−5)の各性状値は以下の通り。重量平均分子量(Mw):22,000、固形分換算の理論アクリロイル基当量:221g/eq、水酸基価253mgKOH/g
・化合物(c−1):ジペンタエリスリトールヘキサアクリレート
・化合物(c−2):トリメチロールプロパントリアクリレート
化合物(c−3)の製造
撹拌装置を備えた反応装置にジシクロヘキシルメタン−4,4’−ジイソシアネート166質量部、ジブチル錫ジラウリート0.2質量部及びメトキノン0.2質量部を加え、攪拌しながら60℃まで昇温した。次いで、ペンタエリスリトールトリアクリレート(東亞合成株式会社製「アロニクスM−305」)630質量部を10回に分けて10分毎に仕込んだ。更に10時間反応させ、赤外線スペクトルで22500cm−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(c−3)を得た。該ウレタンアクリレート(c−3)の各性状値は以下の通り。重量平均分子量(Mw):1,400、理論アクリロイル基当量:120g/eq
前記製造例2で得たアクリル重合体(X−2)のメチルイソブチルケトン溶液20質量部(20質量部中アクリル重合体(X−2)は10.0質量部)、ジペンタエリスリトールヘキサアクリレート(c−1)45質量部、無機微粒子(a−1)45質量部、メチルイソブチルケトン(以下「MIBK」と略記する)80質量部及びプロピレングリコールモノメチルエーテル(以下「PGM」と略記する)10質量部を配合し、不揮発分50質量%のスラリーとしたものを、湿式ボールミル(アシザワ株式会社製「スターミルLMZ015」)を用いて混合分散し、分散体を得た。
メディア:メジアン径100μmのジルコニアビーズ
ミルの内容積に対する樹脂組成物の充填率:70体積%
攪拌翼の先端部の周速:11m/sec
樹脂組成物の流速:200ml/min
分散時間:60分
活性エネルギー線硬化型樹脂組成物中の無機微粒子(A)の動的光散乱法による平均粒子径は、得られた分散体をMIBKで希釈し、濃度5%のMIBK溶液に調整した後、このMIBK溶液を用い、粒子径測定装置(大塚電子株式会社製「ELSZ−2」:「ISO 13321」に準拠。キュムラント法により算出)にて測定した。
前記活性エネルギー線硬化型樹脂組成物を、40℃の温度条件下で1ヶ月間静置し、各経過時における沈降物の有無を評価した。
○:沈降物が見られない
△:3週間後に沈降物が見られる
×:1週間後に沈降物が見られる
1.試験片の作成方法
前記活性エネルギー線硬化型樹脂組成物を、下記プラスチックフィルム上に、硬化後の膜厚がそれぞれ所定の値となるようにバーコーターで塗布し、70℃で1分乾燥させ、窒素下で高圧水銀灯を用いて250mJ/cm2の照射量で通過させて硬化させることにより、硬化塗膜を有する試験片を得た。
・トリアセチルセルロースフィルム(以下「TAC」と略記する)(膜厚80μm)上、10μm
・ポリエチレンテレフタレートフィルム(以下「PET」と略記する)(膜厚188μm)上、10、20、50μm
・ポリメチルメタクレートフィルム(以下「PMMA」と略記する)(膜厚300μm)上、10、20、50μm
2.鉛筆硬度試験方法
上記試験片の硬化被膜をJIS K 5400に従い、トリアセチルセルロールフィルムを基材とするものについては荷重500g、ポリエチレンテレフタレートフィルムを基材とするものについては荷重750g、ポリメチルメタクレートフィルムを基材とするものについては荷重1000gの鉛筆引っかき試験によって評価した。5回試験を行い、1回以上傷がついた硬度の一つ下の硬度を、その塗膜の鉛筆硬度とした。
1.硬化塗膜の作成方法
上記鉛筆硬度試験の場合と同様の方法で試験片を作成した。尚、塗膜の透明性については、試験片全体の膜厚が最も薄いトリアセチルセルロースフィルム(膜厚80μm)上、膜厚10μmの条件で作成した試験片、及び試験片全体の膜厚が最も厚いポリメチルメタクリートフィルム(膜厚188μm)上、膜厚50μmの条件で作成した試験片に対してのみ行った。
2.透明性試験方法
スガ試験機株式会社製「ヘーズコンピュータHZ−2」を用いて塗膜のヘーズ値を測定した。ヘーズ値が低いほど塗膜の透明性は高い。
1.硬化塗膜の作成方法
上記鉛筆硬度試験の場合と同様の方法で塗膜を作成した。尚、塗膜の耐スチールウール性は、基材フィルムの種類による違いがほとんどないことから、試験はトリアセチルセルロースフィルム(膜厚80μm)上、膜厚10μmの条件で作成した試験片に対してのみ行った。
2.耐スチールウール性試験
スチールウール(日本スチールウール株式会社製「ボンスター#0000」0.5gで直径2.4センチメートルの円盤状の圧子を包み、該圧子に1000g重の荷重をかけて評価用フィルムの塗膜層面を100往復させた。試験前後の塗膜のヘーズ値をスガ試験機株式会社製「ヘーズコンピュータHZ−2」を用いて測定し、それらの差δHで評価した。δH値が小さいほど耐擦傷性に優れる硬化塗膜である。
1.硬化塗膜の作成方法
上記鉛筆硬度試験の場合と同様の方法で塗膜を作成した。尚、塗膜の耐カール性は、特にカールが発生しやすいトリアセチルセルロースフィルム(膜厚80μm)上、膜厚10μmの条件で作成した試験片と、ポリエチレンテレフタレートフィルム(膜厚188μm)上、膜厚50μmの条件で作成した試験片に対してのみ行った。
2.耐カール性試験
試験片を10cm四方に切り、4角の水平からの浮きを測定し、その平均値で評価した。値が小さいほどカールが小さく、耐カール性に優れた塗膜である。
1.硬化塗膜の作成方法
上記鉛筆硬度試験の場合と同様の方法で塗膜を作成した。尚、塗膜の折り曲げ性は、該性能が求められることの多いトリアセチルセルロースフィルム(膜厚80μm)上、膜厚10μmの条件で作成した試験片に対してのみ行った。
2.折り曲げ性試験
マンドレル試験機(TP技研社製「屈曲試験機」)を用いて、試験片を試験棒に巻きつけ、フィルムの硬化塗膜層にクラックが生じるか否かを目視確認する試験を行い、クラックが生じない試験棒の最小径を評価結果とした。最小径が小さいほど、折り曲げ性に優れる塗膜である。
1.硬化塗膜の作成方法
上記鉛筆硬度試験の場合と同様の方法で塗膜を作成した。尚、塗膜の耐アルカリ性は、基材フィルムの種類や硬化塗膜層の膜厚による違いがほとんどないことから、試験はトリアセチルセルロースフィルム(膜厚80μm)上、膜厚10μmの条件で作成した試験片に対してのみ行った。
2.耐アルカリ性試験
塗膜に5%水酸化ナトリウム水溶液に浸した脱脂綿(3cm×3cm)を密着させ、乾燥を防ぐためにガラス蓋でカバーを行い、24時間25℃で放置し、塗膜の表面状態を評価した。
○:変化が見られない
△:ブリスターが見られる
×:塗膜が白濁する
組成を表1及び2に示す配合とした以外は実施例1と同様にして活性エネルギー線硬化型樹脂組成物を得た。これらについて実施例1と同様の試験を行った。結果を表1及び2に示す。
前記製造例2で得たアクリル重合体(X−2)のメチルイソブチルケトン溶液40質量部(40質量部中アクリル重合体(X−1)は20.0質量部)、ジペンタエリスリトールヘキサアクリレート(c−1)35質量部、無機微粒子(a−6)150質量部を配合したものを、ホモディスパーを用いて混合分散し、分散体を得た。該分散体ついて実施例1と同様に活性エネルギー線硬化型樹脂組成物を調製し、実施例1と同様の試験を行った。結果を表3に示す
回転速度:2400r/min
分散時間:15分
組成を表3に示す配合とした以外は比較例1と同様にして活性エネルギー線硬化型樹脂組成物を調整し、実施例1と同様の試験を行った。結果を表3に示す。
組成を表3に示す配合とした以外は実施例1と同様にして活性エネルギー線硬化型樹脂組成物を調整し、これらについて実施例1と同様の試験を行った。結果を表3に示す。
前記製造例5で得たアクリル重合体(X−5)のメチルイソブチルケトン溶液24質量部(24質量部中アクリル重合体(X−5)は12.0質量部)、トリメチロールプロパントリアクリレート(c−2)48質量部、ウレタンアクリレート(c−3)25質量部、無機微粒子(a−8)15質量部及びメチルイソブチルケトン10質量部を配合したものを、ホモディスパーを用いて混合分散し、分散体を得た。該分散体ついて実施例1と同様に活性エネルギー線硬化型樹脂組成物を調製し、実施例1と同様の試験を行った。結果を表3に示す
回転速度:2400r/min
分散時間:150分
前記製造例5で得たアクリル重合体(X−5)のメチルイソブチルケトン溶液100質量部(100質量部中アクリル重合体(X−5)は50.0質量部)、無機微粒子(a−9)50質量部及びメチルイソブチルケトン100質量部を配合したものを、平均粒子径0.3mmのジルコニアビーズをメディアとするペイントシェイカーを用いて2時間混合分散し、分散体を得た。該分散体ついて実施例1と同様に活性エネルギー線硬化型樹脂組成物を調製し、実施例1と同様の試験を行った。結果を表3に示す
Claims (12)
- 内部にメディアが充填されたベッセル、回転シャフト、前記回転シャフトと同軸状に回転軸を有し、前記回転シャフトの回転駆動により回転する攪拌翼、前記ベッセルに設置された供給口、前記ベッセルに設置された排出口、及び前記回転シャフトがベッセルを貫通する部分に配設された軸封装置を有する湿式ボールミルであって、前記軸封装置が、2つのメカニカルシールユニットを有し、かつ、該2つのメカニカルシールユニットのシール部が外部シール液によりシールされた構造を有する軸封装置である湿式ボールミルの前記供給口から、平均一次粒子径が3〜100nmの範囲であって、かつ、その粒子表面に(メタ)アクリロイル基構造を有する乾式シリカ微粒子が凝集した二次粒子からなる無機微粒子(a)と、重量平均分子量(Mw)が5,000〜80,000の範囲であり、かつ、分子構造中に(メタ)アクリロイル基を有するアクリル重合体(X)を必須の成分とする樹脂成分とを前記ベッセルに供給し、前記ベッセル内で前記回転シャフト及び前記攪拌翼を回転させて、メディアと原料とを攪拌混合することにより、前記無機微粒子(a)の粉砕と、該無機微粒子(a)の前記樹脂成分への分散とを行い、次いで前記排出口から排出する方法により製造されたものである、動的光散乱法による平均粒子径が95〜250nmの範囲であり、かつ、その粒子表面に、(メタ)アクリロイル基構造を有する乾式シリカからなる無機微粒子(A)と、前記アクリル重合体(X)とを必須の成分として含有し、その不揮発成分100質量部中に前記無機微粒子(A)を35〜60質量部の範囲で含有することを特徴とする活性エネルギー線硬化型樹脂組成物。
- 前記アクリル重合体(X)が、反応性官能基と(メタ)アクリロイル基とを有する化合物(y)を必須の成分として重合させて得られるアクリル重合体(Y)と、前記化合物(y)が有する反応性官能基と反応し得る官能基と(メタ)アクリロイル基とを有する化合物(z)とを反応させて得られる重合体である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記アクリル重合体(Y)が、前記化合物(y)と、その他のアクリル重合性単量体(v)とを、これらの質量比[(y)/(v)]が10/90〜90/10の範囲となるような割合で重合させて得られる重合耐である請求項2記載の活性エネルギー線硬化型樹脂組成物。
- 前記化合物(y)が、エポキシ基と(メタ)アクリロイル基とを有する化合物(y1)であり、かつ、前記化合物(z)が、カルボキシル基と(メタ)アクリロイル基とを有する化合物(z1)である請求項2記載の活性エネルギー線硬化型樹脂組成物。
- 前記アクリル重合体(X)の(メタ)アクリロイル基当量が220〜1650eq/gの範囲である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記アクリル重合体(X)が分子構造中に水酸基を有し、その水酸基当量が35〜250mgKOH/gの範囲である請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 前記ベッセルに供給する樹脂成分として、前記アクリル重合体(X)以外の、分子構造中に(メタ)アクリロイル基を有する化合物(c)を含み、かつ、前記無機微粒子(A)及び前記アクリル重合体(X)に加え、前記アクリル重合体(X)以外の、分子構造中に(メタ)アクリロイル基を有する化合物(c)を含有する請求項1記載の活性エネルギー線硬化型樹脂組成物。
- 請求項1〜7の何れか一つ記載の活性エネルギー線硬化型樹脂組成物を含む塗料。
- 請求項8記載の塗料を硬化させてなる塗膜。
- 請求項9記載の塗膜をプラスチックフィルムの片面又は両面に有する積層フィルム。
- 前記プラスチックフィルムがトリアセチルセルロースフィルム、ポリエチレンテレフタレートフィルム、ポリメチルメタアクリレートフィルムの何れかである請求項10記載の積層フィルム。
- 前記塗膜の膜厚が5〜100μmの範囲である請求項10記載の積層フィルム。
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