JP6965868B2 - 活性エネルギー線硬化性樹脂組成物用帯電防止剤、活性エネルギー線硬化性樹脂組成物、硬化物及びフィルム - Google Patents
活性エネルギー線硬化性樹脂組成物用帯電防止剤、活性エネルギー線硬化性樹脂組成物、硬化物及びフィルム Download PDFInfo
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- JP6965868B2 JP6965868B2 JP2018238055A JP2018238055A JP6965868B2 JP 6965868 B2 JP6965868 B2 JP 6965868B2 JP 2018238055 A JP2018238055 A JP 2018238055A JP 2018238055 A JP2018238055 A JP 2018238055A JP 6965868 B2 JP6965868 B2 JP 6965868B2
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- 238000007754 air knife coating Methods 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- DVQGYGDSAGBRSZ-UHFFFAOYSA-N bis(1-cyclohexylcyclohexa-2,4-dien-1-yl)methanone Chemical compound C1C=CC=CC1(C1CCCCC1)C(=O)C1(C2CCCCC2)CC=CC=C1 DVQGYGDSAGBRSZ-UHFFFAOYSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000001227 electron beam curing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 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 1
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- 239000004611 light stabiliser Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 210000002268 wool Anatomy 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
Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F218/00—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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
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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
- 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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- 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
- C09D5/24—Electrically-conducting paints
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/26—Use as polymer for film forming
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2331/00—Characterised by the use of 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 an acyloxy radical of a saturated carboxylic acid, or carbonic acid, or of a haloformic acid
- C08J2331/02—Characterised by the use of omopolymers or copolymers of esters of monocarboxylic acids
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2339/00—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 at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
- C08J2339/02—Homopolymers or copolymers of vinylamine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
Description
(項目1)
四級アンモニウム塩構造を含むビニルモノマー由来の構成単位(a1)、
水酸基含有ビニルモノマーとラクトンとの開環重付加物であり、かつ、
重量平均分子量が1,000〜10,000であるビニルモノマー由来の構成単位(a2)、
及び
炭素数3〜5の分岐アルキルエステル基を含むビニルモノマー由来の構成単位(a3)を含み、
分子量分布(Mw/Mn)が1.8〜5.0である、ポリマー(A)を含む、
活性エネルギー線硬化性樹脂組成物用帯電防止剤。
(項目2)
上記項目に記載の活性エネルギー線硬化性樹脂組成物用帯電防止剤を含む、活性エネルギー線硬化性樹脂組成物。
(項目3)
上記項目に記載の活性エネルギー線硬化性樹脂組成物の硬化物。
(項目4)
上記項目に記載の硬化物を含む、フィルム。
本開示は、四級アンモニウム塩構造を含むビニルモノマー由来の構成単位(a1)、水酸基含有ビニルモノマーとラクトンとの開環重付加物であり、かつ、重量平均分子量が1,000〜10,000であるビニルモノマー由来の構成単位(a2)、及び炭素数3〜5の分岐アルキルエステル基を含むビニルモノマー由来の構成単位(a3)を含み、分子量分布(Mw/Mn)が1.8〜5.0である、ポリマー(A)を提供する。
四級アンモニウム塩構造を含むビニルモノマー由来の構成単位(a1)は、四級アンモニウム塩構造を含むビニルモノマー(a1’)を用いてポリマーを製造した際にポリマー鎖に含まれる構成単位である。上記ビニルモノマー(a1’)は2種以上を併用できる。
[CH2=C(R1)−C(=O)−A−B−N+(R2)(R3)(R4)]n・Xn−
(式中、R1はH又はCH3、R2〜R4は炭素数1〜3程度のアルキル基を、AはO又はNHを、Bは炭素数1〜3程度のアルキレン基を、X−はカウンターアニオン種を、nは1以上の整数を表す)で表わされる(メタ)アクリレート化合物等が例示される。また、X−は、Cl−、SO4 2−、SO3 −、C2H5SO4 −、Br−等が例示され、帯電防止効果の点よりCl−が最も好ましい。なお、(a1)成分の市販品は、共栄社化学(株)製「ライトエステルDQ−100」、興人(株)製「DMAEA−Q」等が例示される。
水酸基含有ビニルモノマーとラクトンとの開環重付加物であり、かつ、重量平均分子量が1,000〜10,000であるビニルモノマー由来の構成単位(a2)とは、水酸基含有ビニルモノマーとラクトンとの開環重付加物であり、かつ、重量平均分子量が1,000〜10,000であるビニルモノマー(a2’)を用いてポリマーを製造した際にポリマー鎖に含まれる構成単位である。上記ビニルモノマー(a2’)は2種以上を併用できる。
炭素数3〜5の分岐アルキルエステル基を含むビニルモノマー由来の構成単位(a3)とは、炭素数3〜5の分岐アルキルエステル基を含むビニルモノマー(a3’)を用いてポリマーを製造した際にポリマー鎖に含まれる構成単位である。上記ビニルモノマー(a3’)は2種以上を併用できる。1つの実施形態において、上記ビニルモノマー(a3’)は脂環構造を有さない。この場合、構成単位(a3)は脂環構造を有さないものとなる。
上記ポリマーには、上記構成単位(a1)〜(a3)以外の構成単位(a4)(「その他の構成単位(a4)」ともいう)を含んでいてもよい。その他の構成単位(a4)は、上記モノマー(a1’)〜(a3’)以外のモノマー(「その他のモノマー」、「モノマー(a4’)」ともいう)を用いてポリマーを製造した際にポリマー鎖に含まれる構成単位である。その他のモノマーは2種以上を併用できる。
構成単位(a1)と構成単位(a2)との質量比(構成単位(a1)の質量/構成単位(a2)の質量)の上限及び下限は、4、3.5、3、2.5、2、1.5、1、0.5等が例示される。1つの実施形態において、構成単位(a1)と構成単位(a2)との質量比(構成単位(a1)の質量/構成単位(a2)の質量)は0.5〜4が好ましい。
ポリマー(A)の重量平均分子量(Mw)の上限及び下限は、500,000、450,000、400,000、350,000、300,000、250,000、200,000、180,000等が例示される。1つの実施形態において、ポリマー(A)の重量平均分子量(Mw)は180,000〜500,000が好ましい。
(A)成分は、モノマー(a1’)〜(a3’)、及び必要に応じてモノマー(a4’)成分を各種公知の方法(塊状重合、溶液重合、乳化重合等)でラジカル共重合させることにより得られる。反応時間は2〜12時間程度が好ましい。なお、分子量分布は、重合温度や重合開始剤量により調整され得る。
本開示は、上記ポリマー(A)を含む、活性エネルギー線硬化性樹脂組成物用帯電防止剤を提供する。
1つの実施形態において、上記帯電防止剤には希釈溶剤が含まれる。希釈溶剤は2種以上を併用してもよい。希釈溶剤は、メチルエチルケトン、メチルイソブチルケトン、酢酸メチル、酢酸エチル、酢酸ブチル、エタノール、n−プロピルアルコール、イソプロピルアルコール、n−ブタノール、イソブチルアルコール、tert−ブチルアルコール、ジアセトンアルコール、アセチルアセトン、トルエン、キシレン、n−ヘキサン、シクロヘキサン、メチルシクロヘキサン、n−ヘプタン、イソプロピルエーテル、メチルセロソルブ、エチルセロソルブ、1,4−ジオキサン、プロピレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート等が例示される。
上記帯電防止剤は、上記ポリマー(A)でも、希釈溶剤でもない剤を添加剤として含み得る。添加剤は2種以上を併用してもよい。添加剤は、酸化防止剤、紫外線吸収剤、光安定剤、消泡剤、表面調整剤、防汚染剤、顔料、金属酸化物微粒子分散体、有機微粒子分散体等が例示される。
本開示は、上記活性エネルギー線硬化性樹脂組成物用帯電防止剤を含む、活性エネルギー線硬化性樹脂組成物を提供する。上記活性エネルギー線硬化性樹脂組成物は、上記活性エネルギー線硬化性樹脂組成物用帯電防止剤以外に、5個以上の(メタ)アクリロイル基を有するポリ(メタ)アクリレート、反応性希釈剤、光重合開始剤、及び/又は添加剤を含み得る。
5個以上の(メタ)アクリロイル基を有するポリ(メタ)アクリレートは、非ウレタン変性ポリ(メタ)アクリレート(1)((1)成分ともいう)、ウレタン変性ポリ(メタ)アクリレート(2)((2)成分ともいう)等が例示される。5個以上の(メタ)アクリロイル基を有するポリ(メタ)アクリレートは2種以上を併用してもよい。
反応性希釈剤は、上記「5個以上の(メタ)アクリロイル基を有するポリ(メタ)アクリレート」以外の炭素−炭素不飽和結合等の活性エネルギー線反応性官能基を有する化合物である。反応性希釈剤は2種以上を併用してもよい。反応性希釈剤を併用することによって、ポリマー(A)と5個以上の(メタ)アクリロイル基を有するポリ(メタ)アクリレートの相溶性が一層良好になる。その結果、本発明に係る活性エネルギー線硬化性樹脂組成物の透明性が向上し、かつ、帯電防止性、透明性、硬度、及び耐擦傷性等に特に優れた硬化皮膜が得られる。
1つの実施形態において、上記活性エネルギー線硬化性樹脂組成物には、光重合開始剤が含まれる。光重合開始剤は2種以上を併用してもよい。光重合開始剤は、1−ヒドロキシ−シクロヘキシル−フェニルケトン、2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン、1−シクロヘキシルフェニルケトン、2−ヒドロキシ−2−メチル−1−フェニル−プロパン−1−オン、1−[4−(2−ヒドロキシエトキシ)−フェニル]−2−ヒドロキシ−2−メチル−1−プロパン−1−オン、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホリノプロパン−1−オン、2,4,6−トリメチルベンゾイル−ジフェニル−ホスフィンオキサイド、4−メチルベンゾフェノン等が例示される。なお、光重合開始剤は、紫外線硬化を行なう場合に使用されるが、電子線硬化をする場合には、必ずしも必要ではない。
上記組成物は、上記ポリマー(A)、希釈溶剤、5個以上の(メタ)アクリロイル基を有するポリ(メタ)アクリレート、反応性希釈剤、光重合開始剤のいずれでもない剤を添加剤として含み得る。添加剤は2種以上を併用してもよい。添加剤は、上述したもの等が例示される。
本開示は、上記活性エネルギー線硬化性樹脂組成物の硬化物を提供する。上記硬化物は、上記活性エネルギー線硬化性樹脂組成物に、紫外線、電子線、放射線等の活性エネルギー線を照射することにより得られる。
本開示は、上記硬化物を含む、フィルムを提供する。上記フィルムは、上記硬化物と各種ベースフィルムとを構成要素とする物品である。1つの実施形態において、上記フィルムはプラスチックフィルムである。
分子量測定機:製品名「HLC−8320GPC」、東ソー(株)製
カラム:製品名「TSKgel G6000PWXL−CP」、「TSKgel G3000PWXL−CP」、東ソー(株)製
展開溶剤:0.1MのNaNO3及び0.1Mの酢酸溶液
流速:0.5mL/min
試料濃度:0.5g/L
標準物質:ポリエチレンオキサイド(TSKgel標準ポリエチレンオキサイド SE-キット 東ソー(株)製)
合成例1
撹拌装置、冷却管を備えた反応装置に、ヒドロキシエチルメタクリレート130部、ε−カプロラクトン1140部及びオクチル酸スズ1.3部を加え、150℃まで昇温し、6時間保温した後に冷却して、重量平均分子量が約2750である水酸基含有ビニルモノマーとラクトンとの開環重付加物(以下、(a2−1)成分という。)を得た。
標準物質:ポリスチレン(標準ポリスチレンキット PStQuickA、B、C 東ソー(株)製)
という条件で測定したことにより得た値である(以下、同様)。表1に組成と重量平均分子量を示す(以下、同様)。
製造例1
合成例1と同様の反応装置に、メタクリロイルオキシエチルトリメチルアンモニウムクロリド(DMC)(以下、(a1−1)成分という。)100部、(a2−1)成分80部、tert−ブチルメタアクリレート(tBMA)(以下、(a3−1)成分という。)20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という。)800部を加え、80℃まで昇温した。次いで2,2’−アゾビス(メチルブチロニトリル)(以下、AMBNという。)8部及びPGM32部を加え、重合反応を開始、85℃で6時間保温した後に冷却し、四級アンモニウム塩構造含有ポリマー(A−1)の溶液(不揮発分20%)を得た。
表1に記載するように成分を変更した以外は製造例1と同様にして実施した。
iBMA:イソブチルメタアクリレート
CHMA:シクロヘキシルメタクリレート
LMA:ラウリルメタクリレート
実施例1
溶液状の(A−1)成分からなる帯電防止剤を5部、ジペンタエリスリトールヘキサアクリレート(DPHA)(MIWON製、商品名「MIRAMER M600」)を50部、ウレタンアクリレート(荒川化学工業(株)製、商品名「ビームセット577」)を50部、及び1−ヒドロキシ−シクロヘキシル−フェニルケトン(BASFジャパン(株)製、商品名「イルガキュアー184」)を2部、1−[4−(2−ヒドロキシエトキシ)-フェニル]−2−ヒドロキシ-2-メチル−2−プロパン−2−オン(BASFジャパン(株)製、商品名「イルガキュアー2959」)を3部、固形分割合で配合し、PGMで希釈して、不揮発分30%の活性エネルギー線硬化性樹脂組成物を調製した。
100μm膜厚のPETフィルム(東レ(株)製 ルミラー100U483)上に、各活性エネルギー線硬化性樹脂組成物を、硬化後の被膜の膜厚が5μmとなるように#15バーコーターにて塗布し、80℃で1分間乾燥させてフィルムを作製した。次いで、得られたフィルムを紫外線硬化装置(製品名:UBT−080−7A/BM、(株)マルチプライ製、高圧水銀灯600mJ/cm2)を使用し、硬化被膜を供えたフィルムを得た。作製したフィルムに対する下記の評価結果を表2に示す。
フィルムの作製直後の表面抵抗を、市販抵抗率計(三菱化学(株)製、製品名「ハイレスタMCP−HT−450」)を用い、JIS K 6911に準じ、印加電圧500Vで測定した。
1×1011Ω/sq≧・・・〇
1×1011Ω/sq<・・・×
フィルムのヘイズ値を、村上色彩技術研究所製カラーへイズメーターを用いて測定した。
1.0≧・・・〇
1.0<・・・×
フィルムを温度80℃、湿度95%Rh環境下に24時間静置した後、フィルム表面への表面析出物の有無を目視で確認した。
表面析出物なし・・・〇
表面析出物有り・・・×
フィルムの硬化皮膜を、スチールウール(10mm×10mm)を底に貼り付けた重り(500g)で10回擦り、塗膜外観を基準で目視評価した。
傷なし・・・〇
傷有り・・・×
Claims (4)
- ポリマーの全質量に対し、
四級アンモニウム塩構造を含むビニルモノマー由来の構成単位(a1)30〜60質量%、
水酸基含有ビニルモノマーとラクトンとの開環重付加物であり、かつ、
重量平均分子量が1,000〜3,999であるビニルモノマー由来の構成単位(a2)15〜50質量%、及び
炭素数3〜5の分岐アルキルエステル基を含むビニルモノマー由来の構成単位(a3)5〜40質量%を含み、
分子量分布(Mw/Mn)が1.8〜5.0であり、重量平均分子量が184,000〜635,000である、ポリマー(A)を含む、
活性エネルギー線硬化性樹脂組成物用帯電防止剤。 - 請求項1に記載の活性エネルギー線硬化性樹脂組成物用帯電防止剤を含む、活性エネルギー線硬化性樹脂組成物。
- 請求項2に記載の活性エネルギー線硬化性樹脂組成物の硬化物。
- 請求項3に記載の硬化物を含む、フィルム。
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