WO2017002964A1 - 硬化型組成物 - Google Patents
硬化型組成物 Download PDFInfo
- Publication number
- WO2017002964A1 WO2017002964A1 PCT/JP2016/069666 JP2016069666W WO2017002964A1 WO 2017002964 A1 WO2017002964 A1 WO 2017002964A1 JP 2016069666 W JP2016069666 W JP 2016069666W WO 2017002964 A1 WO2017002964 A1 WO 2017002964A1
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- Prior art keywords
- meth
- acrylate
- group
- composition
- component
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- FXUAIOOAOAVCGD-FKSUSPILSA-N swainsonine Chemical compound C1CC[C@H](O)[C@H]2[C@H](O)[C@H](O)CN21 FXUAIOOAOAVCGD-FKSUSPILSA-N 0.000 description 1
- FXUAIOOAOAVCGD-UHFFFAOYSA-N swainsonine Natural products C1CCC(O)C2C(O)C(O)CN21 FXUAIOOAOAVCGD-UHFFFAOYSA-N 0.000 description 1
- 229960005566 swainsonine Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- JIYXDFNAPHIAFH-UHFFFAOYSA-N tert-butyl 3-tert-butylperoxycarbonylbenzoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC(C(=O)OC(C)(C)C)=C1 JIYXDFNAPHIAFH-UHFFFAOYSA-N 0.000 description 1
- DINKXUCRJBUQAZ-UHFFFAOYSA-N tert-butyl 5-bromopyridine-3-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CN=CC(Br)=C1 DINKXUCRJBUQAZ-UHFFFAOYSA-N 0.000 description 1
- LYDRKKWPKKEMNZ-UHFFFAOYSA-N tert-butyl benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1 LYDRKKWPKKEMNZ-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- UWWUTEZECIYOCW-UHFFFAOYSA-N tert-butyl n-(4-hydroxycyclopent-2-en-1-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CC(O)C=C1 UWWUTEZECIYOCW-UHFFFAOYSA-N 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- DLSMLZRPNPCXGY-UHFFFAOYSA-N tert-butylperoxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOOC(C)(C)C DLSMLZRPNPCXGY-UHFFFAOYSA-N 0.000 description 1
- XTXFUQOLBKQKJU-UHFFFAOYSA-N tert-butylperoxy(trimethyl)silane Chemical compound CC(C)(C)OO[Si](C)(C)C XTXFUQOLBKQKJU-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 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
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229940074409 trehalose dihydrate Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 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
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-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
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- IBLKFJNZUSUTPB-UHFFFAOYSA-N trimethyl(pyridin-2-yl)silane Chemical compound C[Si](C)(C)C1=CC=CC=N1 IBLKFJNZUSUTPB-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical group OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000010887 waste solvent Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
- VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940098697 zinc laurate Drugs 0.000 description 1
- 229940105125 zinc myristate Drugs 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
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- KVSXXOUZYJZCPY-UHFFFAOYSA-L zinc;4-cyclohexylbutanoate Chemical compound [Zn+2].[O-]C(=O)CCCC1CCCCC1.[O-]C(=O)CCCC1CCCCC1 KVSXXOUZYJZCPY-UHFFFAOYSA-L 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 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
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 1
- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/50—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from alkaline earth metals, zinc, cadmium, mercury, copper or silver
-
- 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/20—Esters of polyhydric alcohols or polyhydric phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/22—Trihydroxylic alcohols, e.g. glycerol
- C07C31/225—Glycerol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid 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
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/104—Esters of polyhydric alcohols or polyhydric phenols of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L57/00—Compositions of unspecified polymers obtained by reactions only involving 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
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
Definitions
- the present invention relates to a curable composition, and preferably to an active energy ray curable composition.
- the composition of the present invention can be used for various applications, in particular, coating agents such as hard coats, molding materials used in mold transfer and nanoimprinting, inks such as offset and inkjet printing, photosensitive lithographic printing plates And can be preferably used for applications such as pattern forming agents such as color resists and the like, and belongs to these technical fields.
- an acryloyl group and / or a methacryloyl group is represented as a (meth) acryloyl group
- an acrylate and / or methacrylate is represented as a (meth) acrylate
- acrylic acid and / or methacrylic acid is represented by (meth) acrylic acid. It expresses.
- a composition containing a compound having two or more (meth) acryloyl groups (hereinafter referred to as “polyfunctional (meth) acrylate”) is used in various applications, particularly dipentaerythritol.
- a composition mainly composed of a mixture of pentaacrylate and dipentaerythritol hexaacrylate (hereinafter referred to as “DPHA”) or a mixture of pentaerythritol triacrylate and pentaerythritol tetraacrylate (hereinafter referred to as “PETTA”) has excellent physical properties. Is used for various purposes.
- Patent Document 1 A cured film obtained from a composition containing DPHA or / and PETTA is widely used for hard coat applications because of its high surface hardness and resistance to scratching (Patent Document 1). Since DPHA has high viscosity and PETTA is solid at room temperature, it is difficult to make the composition solvent-free.
- Patent Document 2 has a compound having one (meth) acryloyl group (hereinafter referred to as “monofunctional (meth) acrylate”) and two (meth) acryloyl groups in order to reduce the viscosity of DPHA.
- An active energy ray-curable composition containing 30 parts by weight or more of a compound hereinafter referred to as “bifunctional (meth) acrylate” is disclosed.
- Patent Document 2 has a problem that the hardness of the cured film formed on the plastic film is too low.
- DPHA and PETTA are usually produced by dehydration esterification of polyhydric alcohol and acrylic acid, but since these products contain high molecular weight substances, they contribute to a decrease in the hardness of the cured film. Therefore, improvement in hardness is required.
- Patent Document 3 DPHA is widely used as a resin composition for ink applications, particularly active energy ray-curable offset inks, because it has excellent surface curability.
- Patent Document 4 discloses that following the step of removing unreacted acrylic acid, water-soluble components can be removed by washing with a mixture of a specific solvent and water to improve emulsion stability.
- waste solvents and waste liquids increase, there is a demand for a production method capable of reducing the high molecular weight material, instead of this method.
- a composition comprising DPHA or PETTA and an alkali-soluble resin is widely used as an active energy ray-curable pattern-forming resin composition because of its high sensitivity (Patent Document 5). Since DPHA or PETTA is produced by dehydration esterification as described above, alkali metal ions derived from an aqueous alkali metal solution used in the step of removing unreacted acrylic acid remain in the product by 1 ppm or more, Deterioration of electrical characteristics due to elution of metal ions from the cured film may be a problem.
- Patent Document 6 discloses that the elution of metal ions is suppressed by improving the adhesion between the substrate and the cured film, and the specific resistance of the liquid crystal is improved when used in a liquid crystal display device. However, its performance is inadequate and it is required to radically reduce the amount of metal ions in DPHA or PETTA.
- GLY-EO-TA tri (meth) acrylate of ethylene oxide adduct of glycerin
- DGLY-EO-TA tetra (meth) acrylate of diglycerin ethylene oxide adduct
- composition is used for coating applications and ink applications such as offset ink and inkjet ink because of its low viscosity and excellent curability (Patent Documents 7, 8, and 9).
- GLY-EO-TA and DGLY-EO-TA all have an ethylene oxide chain, the acryloyl group concentration is lower than that without an ethylene oxide chain, which contributes to a decrease in the hardness of the cured film.
- DGLY-TA diglycerin tetra (meth) acrylate
- GLY-TA glycerin tri (meth) acrylate
- DGLY-TA and GLY-TA are produced by dehydration esterification of diglycerin and glycerin and acrylic acid, respectively, the reactivity of the secondary hydroxyl group is particularly low and it is difficult to obtain a product. Is not in circulation.
- the phosphine-based catalyst present in the reaction solution after completion of the reaction has a production problem that it is difficult to remove from the reaction solution by a simple method such as filtration and adsorption. It was. For this reason, the phosphine-based catalyst remains in the final product, thereby causing turbidity and catalyst precipitation during storage of the product, and increasing the viscosity or gelation over time. When it is used as a component of the composition, it has the same problem.
- the inventors of the present invention have a low-viscosity composition, a thin film with fast curability, and excellent emulsification resistance and storage stability, and a cured film of the composition has high hardness and excellent alkali developability.
- a curable composition preferably an active energy ray curable composition, intensive studies have been conducted.
- the present inventors can obtain a diglycerol or / and glycerol and a monofunctional (meth) acrylate by transesterification using a specific basic catalyst and a zinc-based catalyst in combination.
- the present inventors have found that a curable composition containing a polyfunctional (meth) acrylate has a low viscosity, is a thin film and is rapidly curable, and is excellent in the hardness of the cured film.
- the present invention will be described in detail.
- composition of the present invention it has a low viscosity, a thin film and fast curability, and further has excellent emulsification resistance and storage stability, and the cured film of the composition has high hardness and excellent alkali developability. Can be.
- the present invention is a compound having diglycerin or / and glycerin (hereinafter referred to as “polyhydric alcohol”) and one (meth) acryloyl group (hereinafter referred to as “monofunctional (meth) acrylate” in the presence of the following catalysts X and Y. It is related with the curable composition containing the mixture (A) of the polyfunctional (meth) acrylate obtained by carrying out transesterification.
- Catalyst X One or more compounds selected from the group consisting of a cyclic tertiary amine having an azabicyclo structure or a salt or complex thereof, an amidine or a salt or complex thereof, and a compound having a pyridine ring or a salt or complex thereof.
- Catalyst Y Compound containing zinc.
- the component (A), other components, and methods of use will be described.
- the component (A) is a polyfunctional (meta) obtained by transesterification of a polyhydric alcohol (diglycerin or / and glycerin) and a monofunctional (meth) acrylate in the presence of the catalysts X and Y. ) A mixture of acrylates. According to the transesterification reaction between the polyhydric alcohol and the monofunctional (meth) acrylate used in combination with the catalysts X and Y, the polyhydric alcohol and (meth) acrylic acid are compared with the dehydration esterification reaction. Therefore, it is possible to produce a polyfunctional (meth) acrylate mixture having low viscosity and few impurities, and thus excellent physical properties.
- the manufacturing method of a polyhydric alcohol, monofunctional (meth) acrylate, catalyst X, catalyst Y, and (A) component is demonstrated.
- diglycerin or / and glycerin are used as (A) component raw material.
- Diglycerin or / and glycerin are preferable in that the cured film of the component (A) to be obtained has high hardness.
- diglycerin or / and glycerin and one or more polyhydric alcohols (hereinafter referred to as “other polyhydric alcohols”) other than diglycerin or / and glycerin are arbitrarily combined. May be used. In the case of using other polyhydric alcohols, 50 parts by weight or less is preferable with respect to 100 parts by weight of diglycerin and / or glycerin.
- polyhydric alcohols include aliphatic alcohols having at least two alcoholic hydroxyl groups in the molecule, alicyclic alcohols, aromatic alcohols, polyhydric alcohol ethers, and other functional groups and bonds in the molecule.
- dihydric alcohol having two alcoholic hydroxyl groups include ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, trimethylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, butanediol, Pentanediol, hexanediol, heptanediol, nonanediol, neopentylglycol, cyclohexanediol, cyclohexanedimethanol, dioxaneglycol, N-methyldiethanolamine, N-ethyldiethanolamine, N-butyldiethanolamine, N-tert-butyldiethanolamine, N- Lauryl diethanolamine, stearyl diethanolamine, N-phenyl Ethanolamine, m-tolyldiethanolamine, p-tolyldiethanolamine, N, N′-bis (2
- trihydric alcohol having three alcoholic hydroxyl groups include trimethylolethane, trimethylolpropane, tris (2-hydroxyethyl) isocyanurate, hexanetriol, octanetriol, decanetriol, triethanolamine, triisopropanolamine.
- tetrahydric alcohol having four alcoholic hydroxyl groups include ditrimethylolethane, ditrimethylolpropane, pentaerythritol, N, N, N ′, N′-tetrakis (2-hydroxyethyl) butanediamide, N, N , N ′, N′-tetrakis (2-hydroxypropyl) butanediamide, N, N, N ′, N′-tetrakis (2-hydroxyethyl) hexanediamide, N, N, N ′, N′-tetrakis (2- Hydroxypropyl) hexanediamide, N, N, N ′, N′-tetrakis (2-hydroxyethyl) ethylenediamine, N, N, N ′, N′-tetrakis (2-hydroxypropyl) ethylenediamine, N-hexanoyl-D— Glucosamine, N-valeryl-D-
- pentahydric alcohols having five alcoholic hydroxyl groups include tritrimethylolethane, tritrimethylolpropane, triglycerin, bis (2-hydroxyethyl) aminotris (hydroxymethyl) methane, bis (2-hydroxypropyl) Aminotris (hydroxymethyl) methane, N, N, N ′, N ′′, N ′′ -pentakis (2-hydroxyethyl) diethylenetriamine, N, N, N ′, N ′′, N ′′ -pentakis (2 -Hydroxypropyl) diethylenetriamine, miglitol, erythromycin, azithromycin dihydrate, D-(+)-arabitol, DL-arabitol, L-(-)-arabitol, D-(-)-fructose, L-(+)- Fructose, D-(+)-galactose, L-(-)-galactose , ⁇ -D
- polyhydric alcohol having 6 or more alcoholic hydroxyl groups include polytrimethylolethane, polytrimethylolpropane, polyglycerin, dipentaerythritol, tripentaerythritol, polypentaerythritol, iohexol, galactitol, D- Sorbitol, L-sorbitol, myo-inositol, scyllo-inositol, D-mannitol, L-mannitol, icariin, amygdalin, D-(+)-cellobiose, diosmin, 2-O- ⁇ -D-glucopyranosyl-L-ascorbic acid , Hesperidin, D-(+)-lactose monohydrate, lactulose, D-(+)-maltose monohydrate, D-(+)-melibiose monohydrate, methyl hesperidin, maltitol,
- the monofunctional (meth) acrylate used as a raw material for the monofunctional (meth) acrylate (A) component is a compound having one (meth) acryloyl group in the molecule.
- it is represented by the following general formula (1).
- R 1 represents a hydrogen atom or a methyl group.
- R 2 represents an organic group having 1 to 50 carbon atoms.
- R 2 in the general formula (1) include methyl group, ethyl group, n- or i-propyl group, n-, i- or t-butyl group, n-, s- or t-amyl group.
- Neopentyl group Neopentyl group, n-, s- or t-hexyl group, n-, s- or t-heptyl group, n-, s- or t-octyl group, 2-ethylhexyl group, capryl group, nonyl group, decyl group , Undecyl group, lauryl group, tridecyl group, myristyl group, pentadecyl group, cetyl group, heptadecyl group, stearyl group, nonadecyl group, aralkyl group, seryl group, myricyl group, melicyl group, vinyl group, allyl group, methallyl group, crotyl group 1,1-dimethyl-2-propenyl group, 2-methylbutenyl group, 3-methyl-2-butenyl group, 3-methyl-3-butenyl group, 2-methyl-3-butenyl group, butene
- R 2 is an alkyl having 1 to 8 carbon atoms such as methyl, ethyl, propyl, pentyl, butyl, heptyl, octyl, heptyl and 2-ethylhexyl among these functional groups.
- Group, alkoxyalkyl group such as methoxyethyl group, ethoxyethyl group and methoxybutyl group, N, N-dimethylaminoethyl group, N, N-diethylaminoethyl group, N, N-dimethylaminopropyl group, N, N-diethylamino
- a dialkylamino group such as a propyl group is preferred.
- these monofunctional (meth) acrylates can be used alone or in combination of two or more.
- carbon such as methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate and i-butyl (meth) acrylate and 2-ethylhexyl (meth) acrylate
- Alkyl (meth) acrylates having an alkyl group of 1 to 8 and alkoxyalkyl (meth) acrylates such as 2-methoxyethyl acrylate and N, N-dimethylaminoethyl (meth) acrylate are preferable, and most polyhydric alcohols are particularly preferable.
- (Meth) acrylates having an alkyl group having 1 to 4 carbon atoms and alkoxyalkyl (meth) acrylates having an alkyl group having 1 to 2 carbon atoms, which are easily available and easily available, are preferred. Furthermore, alkoxyalkyl (meth) acrylates having an alkyl group having 1 to 2 carbon atoms that promote dissolution of polyhydric alcohol and exhibit very good reactivity are more preferable, and 2-methoxyethyl (meth) acrylate is particularly preferable. Furthermore, as monofunctional (meth) acrylate, acrylate is particularly preferable because of its excellent reactivity.
- the transesterification reaction catalyst in the production method of the catalyst (A) component has a low viscosity and a small amount of impurities because there are few high molecular weight compounds in the component (A).
- the following catalysts X and Y are used in combination as a catalyst because an acrylate mixture can be produced.
- Catalyst X Cyclic tertiary amine having an azabicyclo structure or a salt or complex thereof (hereinafter referred to as “azabicyclo compound”), amidine or a salt or complex thereof (hereinafter referred to as “amidine compound”), and a compound having a pyridine ring Or one or more compounds selected from the group consisting of salts or complexes thereof (hereinafter referred to as “pyridine compounds”).
- Catalyst Y Compound containing zinc.
- the catalyst X and the catalyst Y will be described.
- the catalyst X in the method for producing the component (A) is one or more compounds selected from the group consisting of an azabicyclo compound, an amidine compound, and a pyridine compound. These compounds used as the catalyst X are excellent in catalytic activity and can preferably produce the component (A), and also form a complex with the catalyst Y described later after completion of the reaction, and the complex is obtained after completion of the reaction by a simple method such as adsorption. It can be easily removed from the reaction solution. In particular, since the complex with the catalyst Y becomes hardly soluble in the reaction solution, the azacyclo compound can be more easily removed by filtration and adsorption.
- the phosphine compound is excellent in catalytic activity, it is difficult to form a complex with the catalyst Y, or when the complex is formed, it is easily soluble in the reaction solution, and the phosphine compound in the reaction solution after the completion of the reaction. Since most of the compound or complex remains dissolved, it is difficult to remove from the reaction solution by a simple method such as filtration and adsorption. For this reason, the phosphine-based catalyst remains in the final product, thereby causing turbidity and catalyst precipitation during storage of the product, and increasing the viscosity or gelation over time. When it is used as a component of the composition, it has the same problem.
- azabicyclo compounds include 1-azabicyclo [1,1,0] butane, 1,3-diazabicyclo [1,1,0] butane, 1-azabicyclo [2,1,0] heptane, 1,3 -Diazabicyclo [2,1,0] heptane, 1,4-diazabicyclo [2,1,0] heptane, 1-azabicyclo [2,2,0] hexane, 1,3-diazabicyclo [2,2,0] hexane 1-azabicyclo [2,1,1] hexane, 1,3-diazabicyclo [2,1,1] hexane, 1-azabicyclo [2,2,1] heptane, 1,3-diazabicyclo [2,2,1 ] Heptane, 1,4-diazabicyclo [2,2,1] heptane, 1-azabicyclo [3,2,0] heptane, 1,3-diazabicyclo [3,2,0] h
- DABCO hexamethylenetetramine, 3-quinolidinone hydrochloride, 3-chloro-1-azabicyclo [2,2,2] octane hydrochloride, cinchonidine dihydrochloride, cinchonine hydrochloride hydrate, cinchonidine sulfate Dihydrate, hydroquinidine hydrochloride, cinchonine sulfate dihydrate, quinine hydrochloride dihydrate, quinine sulfate dihydrate, quinine phosphate, quinidine sulfate dihydrate, mianserin hydrochloride, 1 , 1 ′-(butane-1,4-diyl) bis [4-aza-1-azoniabicyclo [2,2,2] octane] dibromide, 1,1 ′-(decane-1,10-diyl) bis [4 -Aza-1-azoniabicyclo [2,2,2] o
- amidine compounds include imidazole, N-methylimidazole, N-ethylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1-vinylimidazole, 1-allylimidazole, 1 , 8-diazabicyclo [5,4,0] undec-7-ene (hereinafter referred to as “DBU”), 1,5-diazabicyclo [4,3,0] non-5-ene (hereinafter referred to as “DBN”) N-methylimidazole hydrochloride, DBU hydrochloride, DBN hydrochloride, N-methylimidazole acetate, DBU acetate, DBN acetate, N-methylimidazole acrylate, DBU acrylate, DBN acrylate, phthalimide DBU etc. are mentioned.
- pyridine compounds include pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2-ethylpyridine, 3-ethylpyridine, 4-ethylpyridine, 2-propylpyridine, 4-propylpyridine.
- these catalysts X can be used alone or in any combination of two or more.
- quinuclidine, 3-quinuclidinone, 3-hydroxyquinuclidine, DABCO, N-methylimidazole, DBU, DBN and DMAP are preferable, and particularly have good reactivity with most polyhydric alcohols.
- the readily available 3-hydroxyquinuclidine, DABCO, N-methylimidazole, DBU and DMAP are preferred.
- the amount of the catalyst X used in the production method of the component (A) is not particularly limited, but 0.0001 to 0.5 mol of the catalyst X is preferably used with respect to 1 mol of hydroxyl groups in the polyhydric alcohol. More preferably, it is 0.0005 to 0.2 mol.
- 0.0001 mol or more of catalyst X the production amount of the target polyfunctional (meth) acrylate can be increased, and by setting it to 0.5 mol or less, the production of by-products and the reaction solution Coloring can be suppressed, and the purification step after completion of the reaction can be simplified.
- the catalyst Y is a compound containing zinc.
- various compounds can be used as long as they contain zinc, but organic acids zinc and zinc diketone enolate are preferable because of excellent reactivity.
- organic acid zinc include dibasic acid zinc such as zinc oxalate and a compound represented by the following general formula (3).
- R 6 and R 7 are each a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched alkenyl group having 1 to 20 carbon atoms, or a 6 to 24 carbon atoms.
- An aryl group or a cycloalkyl group having 5 to 20 carbon atoms is meant.
- R 6 and R 7 may be the same or different.
- the compound of the formula (3) is preferably a compound in which R 6 and R 7 are linear or branched alkyl groups having 1 to 20 carbon atoms.
- the linear or branched alkyl group having 1 to 20 carbon atoms is a functional group having no halogen atom such as fluorine and chlorine, and the catalyst Y having the functional group has a high yield. Is preferable because a polyfunctional (meth) acrylate can be produced.
- Examples of zinc diketone enolate include compounds represented by the following general formula (4).
- R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are each a linear or branched alkyl group having 1 to 20 carbon atoms or a linear chain having 1 to 20 carbon atoms. Or a branched alkenyl group, an aryl group having 6 to 24 carbon atoms, or a cycloalkyl group having 5 to 20 carbon atoms.
- R 8 , R 9 , R 10 , R 11 , R 12 and R 13 may be the same or different.
- the compound containing zinc represented by the general formula (3) include zinc acetate, zinc acetate dihydrate, zinc propionate, zinc octylate, zinc neodecanoate, zinc laurate, zinc myristate, Examples include zinc stearate, zinc cyclohexanebutyrate, zinc 2-ethylhexanoate, zinc benzoate, zinc t-butylbenzoate, zinc salicylate, zinc naphthenate, zinc acrylate, and zinc methacrylate.
- this complex with the hydrate, solvate, and catalyst X is also component (A). It can be used as the catalyst Y in the production method.
- the compound containing zinc represented by the general formula (4) include zinc acetylacetonate, zinc acetylacetonate hydrate, bis (2,6-dimethyl-3,5-heptanedionate) zinc, bis (2,2,6,6-tetramethyl-3,5-heptanedionato) zinc, bis (5,5-dimethyl-2,4-hexanedionato) zinc and the like.
- these compounds containing zinc when the complex with the hydrate or solvate, or the catalyst X exists, this complex with the hydrate, the solvate, and the catalyst X is also component (A). It can be used as the catalyst Y in the production method.
- the organic acid zinc and zinc diketone enolate in the catalyst Y can be used directly, but these compounds can also be generated and used in the reaction system.
- zinc compounds such as metal zinc, zinc oxide, zinc hydroxide, zinc chloride and zinc nitrate (hereinafter referred to as “raw zinc compounds”) are used as raw materials.
- raw zinc compounds In the case of organic acid zinc, raw zinc compounds and organic acids
- zinc diketone enolate a method of reacting a raw material zinc compound with 1,3-diketone and the like can be mentioned.
- these catalysts Y can be used alone or in any combination of two or more.
- zinc acetate, zinc propionate, zinc acrylate, zinc methacrylate, and zinc acetylacetonate are preferable, and particularly shows good reactivity with most polyhydric alcohols and is easily available.
- Zinc acetate, zinc acrylate and zinc acetylacetonate are preferred.
- the amount of catalyst Y used in the method for producing component (A) is not particularly limited, but 0.0001 to 0.5 mol of catalyst Y is preferably used with respect to 1 mol of total hydroxyl groups in the polyhydric alcohol. More preferably, it is 0.0005 to 0.2 mol.
- 0.0001 mol or more of catalyst Y the production amount of the target polyfunctional (meth) acrylate can be increased, and by setting it to 0.5 mol or less, by-product formation and reaction solution Coloring can be suppressed, and the purification step after completion of the reaction can be simplified.
- Component (A) is produced by transesterification of polyhydric alcohol and monofunctional (meth) acrylate in the presence of catalysts X and Y.
- the ratio of the catalyst X and the catalyst Y in the method for producing the component (A) is not particularly limited, but it is preferable to use 0.005 to 10.0 moles of the catalyst X with respect to 1 mole of the catalyst Y.
- the amount is preferably 0.05 to 5.0 mol.
- the production amount of the target polyfunctional (meth) acrylate can be increased, and by making it 10.0 mol or less, the generation of by-products and coloring of the reaction liquid are suppressed.
- the purification process after completion of the reaction can be simplified.
- the catalyst X is an azabicyclo compound
- the catalyst Y is preferably a combination of compounds represented by the general formula (3)
- the azabicyclo compound is DABCO.
- a combination in which the compound represented by the general formula (3) is zinc acetate and / or zinc acrylate is most preferable.
- this combination is excellent in color tone after completion of the reaction, and thus can be suitably used for various industrial applications in which color tone is regarded as important.
- the catalyst is available at a relatively low cost, it is an economically advantageous production method.
- the catalyst X and catalyst Y used in the present invention may be added from the beginning of the above reaction or may be added in the middle. Moreover, a desired use amount may be added all at once, or may be added in divided portions.
- the reaction temperature in the method for producing the component (A) is preferably 40 to 180 ° C, more preferably 60 to 160 ° C.
- the reaction rate can be increased, and by setting it to 180 ° C. or lower, thermal polymerization of (meth) acryloyl groups in raw materials and products is suppressed, and coloring of the reaction liquid is performed. And the purification process after completion of the reaction can be simplified.
- the reaction pressure in the method for producing the component (A) is not particularly limited as long as the predetermined reaction temperature can be maintained, and may be performed in a reduced pressure state or in a pressurized state. Usually, it is 0.000001 to 10 MPa (absolute pressure).
- monohydric alcohol derived from monofunctional (meth) acrylate is by-produced as the transesterification proceeds.
- the monohydric alcohol may be allowed to coexist in the reaction system, the transesterification reaction can be further promoted by discharging the monohydric alcohol out of the reaction system.
- the reaction can be carried out without using a solvent, but a solvent may be used as necessary.
- a solvent include n-hexane, cyclohexane, methylcyclohexane, n-heptane, n-octane, n-nonane, n-decane, benzene, toluene, xylene, ethylbenzene, diethylbenzene, isopropylbenzene, amylbenzene, diamyl.
- Hydrocarbons such as benzene, triamylbenzene, dodecylbenzene, didodecylbenzene, amyltoluene, isopropyltoluene, decalin and tetralin; diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, diamyl ether, diethyl acetal, dihexyl acetal , T-butyl methyl ether, cyclopentyl methyl ether, tetrahydrofuran, tetrahydropyran, trioxane, dioxane, anisole, diphenyl ether Ethers such as tellurium, dimethylcellosolve, diglyme, triglyme and tetraglyme; crown ethers such as 18-crown-6; esters such as methyl benzoate and ⁇ -butyrolactone; acetone, methyl e
- an inert gas such as argon, helium, nitrogen and carbon dioxide may be introduced into the system for the purpose of maintaining a good color tone of the reaction solution, but a (meth) acryloyl group
- an oxygen-containing gas may be introduced into the system.
- the oxygen-containing gas include air, a mixed gas of oxygen and nitrogen, a mixed gas of oxygen and helium, and the like.
- a method for introducing the oxygen-containing gas there is a method in which the oxygen-containing gas is dissolved in the reaction solution or blown into the reaction solution (so-called bubbling).
- a polymerization inhibitor in the reaction liquid for the purpose of preventing the polymerization of the (meth) acryloyl group.
- the polymerization inhibitor include hydroquinone, tert-butylhydroquinone, hydroquinone monomethyl ether, 2,6-di-tert-butyl-4-methylphenol, 2,4,6-tri-tert-butylphenol, 4-tert -Butylcatechol, benzoquinone, phenothiazine, N-nitroso-N-phenylhydroxylamine ammonium, 2,2,6,6-tetramethylpiperidine-1-oxyl, 4-hydroxy-2,2,6,6-tetramethylpiperidine
- Organic polymerization inhibitors such as -1-oxyl
- inorganic polymerization inhibitors such as copper chloride, copper sulfate and iron sulfate
- organic salt systems such as copper dibutyldithiocarbamate and N-nitro
- a polymerization inhibitor may be added individually by 1 type, or may be added in combination of 2 or more types, may be added from the beginning of this invention, and may be added from the middle. Moreover, a desired use amount may be added all at once, or may be added in divided portions. Moreover, you may add continuously via a rectification column.
- the addition ratio of the polymerization inhibitor is preferably 5 to 30,000 wtppm in the reaction solution, more preferably 25 to 10,000 wtppm. By setting this ratio to 5 wtppm or more, the polymerization inhibition effect can be exerted, and by setting it to 30,000 wtppm or less, coloring of the reaction solution can be suppressed, and the purification step after completion of the reaction can be simplified. Moreover, the fall of the cure rate of the (A) component obtained can be prevented.
- reaction time in the production method of component (A) varies depending on the type and amount of catalyst used, reaction temperature, reaction pressure, etc., but is usually 0.1 to 150 hours, preferably 0.5 to 80 hours.
- the manufacturing method of a component can be implemented by any method of a batch type, a semibatch type, and a continuous type.
- a batch system a polyhydric alcohol, a monofunctional (meth) acrylate, a catalyst, and a polymerization inhibitor are charged into a reactor, and stirred at a predetermined temperature while bubbling oxygen-containing gas into the reaction solution. Then, it can implement by the method of producing
- the separation / purification operation include a crystallization operation, a filtration operation, a distillation operation, and an extraction operation, and these are preferably combined.
- the crystallization operation include cooling crystallization and concentration crystallization.
- the filtration operation include pressure filtration, suction filtration, and centrifugal filtration.
- the distillation operation include single distillation, fractional distillation, and molecular distillation.
- steam distillation, and the extraction operation includes solid-liquid extraction and liquid-liquid extraction.
- a solvent may be used in the separation and purification operation.
- a neutralizing agent for neutralizing the catalyst and / or polymerization inhibitor used in the present invention an adsorbing agent for adsorbing and removing, an acid and / or alkali for decomposing or removing by-products, a color tone Activated carbon for improving diatomaceous earth, diatomaceous earth for improving filtration efficiency and filtration speed, and the like may be used.
- a preferred component (A) component (A) is a mixture of a polyfunctional (meth) acrylate obtained by transesterification of a polyhydric alcohol (diglycerin or / and glycerin) and a monofunctional (meth) acrylate, and has a hydroxyl group. It is a mixture of polyfunctional (meth) acrylate and polyfunctional (meth) acrylate having a hydroxyl group. For example, in the case of diglycerin, it is a mixture of diglycerin di (meth) acrylate, diglycerin tri (meth) acrylate and diglycerin tetra (meth) acrylate.
- a (meth) acrylate mixture mainly composed of diglycerin tri (meth) acrylate and diglycerin tetra (meth) acrylate is preferable.
- glycerin it is a mixture of glycerin di (meth) acrylate and glycerin tri (meth) acrylate.
- a (meth) acrylate mixture containing glycerin tri (meth) acrylate as a main component is preferable.
- the mixture of polyfunctional (meth) acrylates may contain a small amount of mono (meth) acrylate.
- the hydroxyl value is preferably 60 mgKOH / g or less, more preferably 45 mgKOH / g or less.
- the hydroxyl value means the number of mg of potassium hydroxide equivalent to the hydroxyl group in 1 g of a sample.
- the component (A) is a mixture of various polyfunctional (meth) acrylates as described above, but it is preferable to use a component with a small proportion of the high molecular weight substance that is a side reaction product.
- the high molecular weight substance in the component (A) is a value obtained by gel permeation chromatography (hereinafter referred to as “GPC”) measurement, and is an area% of the high molecular weight substance defined by the following formula (1). Is preferably less than 30%.
- High molecular weight area% [(R ⁇ IL) / R] ⁇ 100 (1)
- the symbols and terms in formula (1) mean the following.
- R total area of detection peaks in component (A) I: area of detection peaks containing ideal structure (meth) acrylate L: weight average molecular weight (hereinafter referred to as detection peak containing ideal structure (meth) acrylate) Total area of detection peak with small (Mw) and ideal structure (meth) acrylate: The number of hydroxyl groups contained per molecule of raw alcohol and the same number of (meth) acryloyl groups per molecule, and Michael addition A polyfunctional (meth) acrylate having no mold structure is meant.
- Mw means a value obtained by converting a molecular weight measured by GPC using tetrahydrofuran (hereinafter referred to as “THF”) as a solvent based on the molecular weight of polystyrene.
- the molecular weight measured by GPC in the present invention means a value measured under the following conditions.
- ⁇ Detector Differential refractometer (RI detector) -Column type: Cross-linked polystyrene column-Column temperature: within 25-50 ° C-Eluent: THF
- Curable composition TECHNICAL FIELD This invention relates to the curable composition containing the said (A) component.
- a method for producing the composition there is a production method comprising a step of producing a mixture of a polyfunctional (meth) acrylate by subjecting a polyhydric alcohol and a monofunctional (meth) acrylate to a transesterification reaction in the presence of the catalysts X and Y. preferable.
- the component (A) can be produced in a high yield, and since the high molecular weight product in the obtained component (A) is small, the viscosity is low and there are few impurities. This is preferable in that it can be excellent in physical properties. What is necessary is just to follow the manufacturing method of above-described (A) component as the said process.
- the component (A) When used for a preferred application such as a coating agent, ink, and pattern formation, it may be appropriately set according to the purpose, preferably 1 to 100,000 mPa ⁇ s, more preferably 5 to 50, 000 mPa ⁇ s. By setting it as the said viscosity range, it is excellent in the leveling property at the time of the coating of a composition, and shall be excellent in the external appearance of hardened
- the viscosity in the present invention means a value measured at 25 ° C. using an E-type viscometer.
- composition of this invention can be used for both an active energy ray hardening-type composition and a thermosetting type composition, an active energy ray hardening-type composition is preferable.
- the composition of the present invention contains (A) as an essential component, but various components can be blended depending on the purpose. Specific examples of other components include a photopolymerization initiator (hereinafter referred to as “component (B)”), a thermal polymerization initiator (hereinafter referred to as “component (C)”), and ethylene other than the component (A). And a compound having an unsaturated group (hereinafter referred to as “component (D)”) and an organic solvent (hereinafter referred to as “component (E)”).
- component (B) a photopolymerization initiator
- component (C) thermal polymerization initiator
- component (E) organic solvent
- composition of the present invention when used as an active energy ray curable composition and further used as an electron beam curable composition, it does not contain the component (B) (photopolymerization initiator) and is an electron. It can also be cured by a wire.
- component (B) photopolymerization initiator
- the component (B) is further added from the viewpoint of ease of curing and cost. It is preferable to contain.
- an electron beam is used as the active energy ray, it is not always necessary to add it, but a small amount can be added as necessary in order to improve curability.
- component (B) examples include benzyl dimethyl ketal, benzyl, benzoin, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropane- 1-one, 1- [4- (2-hydroxyethoxy) phenyl] -2-hydroxy-2-methyl-1-propan-1-one, oligo [2-hydroxy-2-methyl-1- [4-1 -(Methylvinyl) phenyl] propanone, 2-hydroxy-1- [4- [4- (2-hydroxy-2-methyl-propionyl) benzyl] phenyl] -2-methylpropan-1-one, 2-methyl- 1- [4- (Methylthio)] phenyl] -2-morpholinopropan-1-one 2-Benzyl-2-dimethylamino-1- (4-morpholinophenyl)
- ⁇ -hydroxyphenyl ketones are preferable because they have good surface curability even in the case of thin film coating in the atmosphere.
- 1-hydroxycyclohexyl phenyl ketone and 2-hydroxy-2 -Methyl-1-phenyl-propan-1-one is more preferred.
- the content of the component (B) is preferably 0.1 to 10 parts by weight, more preferably 0.5 to 8 parts by weight with respect to 100 parts by weight of the total amount of the curable components.
- the “curable component” is a component that is cured by heat or active energy rays, and means the component (A).
- (D) and ( D) means a component.
- thermosetting type composition a thermal-polymerization initiator can be mix
- Various compounds can be used as the thermal polymerization initiator, and organic peroxides and azo initiators are preferred.
- organic peroxide examples include 1,1-bis (t-butylperoxy) 2-methylcyclohexane, 1,1-bis (t-hexylperoxy) -3,3,5-trimethylcyclohexane, , 1-bis (t-hexylperoxy) cyclohexane, 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, 1,1-bis (t-butylperoxy) cyclohexane, , 2-bis (4,4-di-butylperoxycyclohexyl) propane, 1,1-bis (t-butylperoxy) cyclododecane, t-hexylperoxyisopropyl monocarbonate, t-butylperoxymaleic acid, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxylaurate, 2,5-dimethyl- , 5-di (m
- azo compound examples include 1,1′-azobis (cyclohexane-1-carbonitrile), 2- (carbamoylazo) isobutyronitrile, 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile. Azodi-t-octane, azodi-t-butane, and the like. These may be used alone or in combination of two or more. Moreover, an organic peroxide can also be made into a redox reaction by combining with a reducing agent.
- thermal polymerization initiators used is preferably 10 parts by weight or less with respect to 100 parts by weight of the total amount of curable components.
- thermal polymerization initiator may be carried out in accordance with conventional means of normal radical thermal polymerization. In some cases, it is used in combination with the component (B) (photopolymerization initiator).
- thermosetting can also be performed.
- Component (D) is an ethylenically unsaturated compound other than the component (A), and is blended for the purpose of imparting various physical properties to the cured product of the composition.
- the ethylenically unsaturated group in component (D) include a (meth) acryloyl group, a (meth) acrylamide group, a vinyl group, and a (meth) allyl group, and a (meth) acryloyl group is preferred.
- “monofunctional” means a compound having one ethylenically unsaturated group
- ⁇ functional means a compound having ⁇ ethylenically unsaturated groups
- polyfunctional Means a compound having two or more ethylenically unsaturated groups.
- specific examples of the monofunctional ethylenically unsaturated compound include compounds similar to the monofunctional (meth) acrylate described above, and include methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) ) Acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate and tert-butylcyclohexyl (meth) acrylate and 2-methoxyethyl acrylate are preferred.
- Examples of compounds other than the above-mentioned monofunctional (meth) acrylate include (meth) acrylic acid, Michael addition dimer of acrylic acid, ⁇ -carboxy-polycaprolactone mono (meth) acrylate, monohydroxyethyl (meth) acrylate phthalate , Ethyl carbitol (meth) acrylate, butyl carbitol (meth) acrylate, 2-ethylhexyl carbitol (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, (meth) acrylate of an alkylene oxide adduct of phenol (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl acrylate of alkylene oxide adduct of alkylphenol (Meth) acrylates of alkylene oxide adducts of paraxamylphenol
- bifunctional (meth) acrylate compound examples include polyethylene glycol di (meth) acrylate, ethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, and tetramethylene glycol.
- epoxy (meth) acrylate having a bisphenol skeleton, polyether skeleton, polyalkylene skeleton, polyester skeleton, urethane (meth) acrylate having a polyether skeleton or a polycarbonate skeleton, and polyester (meth) acrylate may also be used. Can do.
- Examples of the tri- or higher functional (meth) acrylate compound include various compounds as long as the compound has three or more (meth) acryloyl groups.
- Polyol poly (meth) acrylates such as (meth) acrylate, tritrimethylolpropane tri- or tetra (meth) acrylate and dipentaerythritol tri-, tetra-, penta- or hexa (meth) acrylate;
- alkylene oxide adduct examples include ethylene oxide adduct, propylene oxide adduct, ethylene oxide and propylene oxide adduct, and the like.
- organic polyisocyanate examples include hexamethylene diisocyanate, tetramethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, isophorone diisocyanate, norbornane diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated 4,4′-diphenylmethane diisocyanate, hydrogenated xylylene.
- the content ratio of the component (D) is preferably 0 to 60% by weight, more preferably 0 to 30% by weight in 100 parts by weight of the total amount of the curable component.
- composition of this invention can contain the organic solvent of (E) component for the purpose of improving the coating property to a base material.
- component (E) examples include alcohol compounds such as methanol, ethanol, isopropanol and butanol; alkylene glycol monoether compounds such as ethylene glycol monomethyl ether and propylene glycol monomethyl ether; acetone alcohols such as diacetone alcohol; benzene and toluene And aromatic compounds such as xylene; ester compounds such as propylene glycol monomethyl ether acetate, ethyl acetate and butyl acetate; ketone compounds such as acetone, methyl ethyl ketone and methyl isobutyl ketone; ether compounds such as dibutyl ether; and N-methylpyrrolidone Can be mentioned.
- alkylene glycol monoether compounds and ketone compounds are preferable, and alkylene glycol monoether compounds are more preferable.
- the content of component (E) is preferably 10 to 1,000 parts by weight, more preferably 50 to 500 parts by weight, and more preferably 50 to 300 parts by weight with respect to 100 parts by weight of the total amount of the curable components. More preferably, it is part by weight.
- the composition can have a viscosity suitable for coating, and the composition can be easily applied by a known application method described later.
- composition of the present invention can be used for various applications.
- preferred applications include coating compositions such as hard coats, compositions for molding materials used in mold transfer and nanoimprinting, ink compositions such as offset and inkjet printing, photosensitive lithographic printing plates and color resists. And the like, and the like.
- coating compositions such as hard coats, compositions for molding materials used in mold transfer and nanoimprinting, ink compositions such as offset and inkjet printing, photosensitive lithographic printing plates and color resists. And the like, and the like.
- composition for Coating The composition of the present invention is excellent in thin film curability and has a high hardness of the cured product, so that it can be preferably used as a composition for coating. It can be more preferably used as a coating composition.
- the coating composition can be preferably used as a hard coat application, and can be more preferably used as a solvent-free hard coat agent.
- a base material a plastic film used for a polarizer protective film or an antireflection film, home appliances Examples include resin molded products used for products and automobile interior and exterior parts.
- the coating composition contains the component (A) as an essential component, but various components can be blended depending on the purpose. Specifically, as other components, in addition to the components (B), (C), (D) and (E) described above, an antioxidant, an ultraviolet absorber, a pigment / dye, a silane coupling agent, a surface modification agent. Examples include a quality agent, a polymer, and a polymerization inhibitor. Hereinafter, these components will be described. In addition, the other component mentioned later may use only 1 type of the illustrated compound, and may use 2 or more types together.
- Antioxidant Antioxidant is mix
- the antioxidant include phenol-based antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants.
- phenolic antioxidants include hindered phenols such as di-t-butylhydroxytoluene.
- commercially available products include AO-20, AO-30, AO-40, AO-50, AO-60, AO-70, and AO-80 manufactured by Adeka Corporation.
- Examples of the phosphorus-based antioxidant include phosphines such as trialkylphosphine and triarylphosphine, and trialkyl phosphites and triaryl phosphites.
- the content ratio of the antioxidant may be appropriately set according to the purpose, and is preferably 0.01 to 5 parts by weight, more preferably 0.1 to 1 part by weight with respect to 100 parts by weight of the total amount of the curable components. It is. When the content ratio is 0.1 parts by weight or more, the durability of the composition can be improved. On the other hand, when the content ratio is 5 parts by weight or less, curability and adhesion can be improved.
- UV absorber An ultraviolet absorber is mix
- the ultraviolet absorber include triazine ultraviolet absorbers such as TINUVIN400, TINUVIN405, TINUVIN460, and TINUVIN479 manufactured by BASF, and benzotriazole ultraviolet absorbers such as TINUVIN900, TINUVIN928, and TINUVIN1130.
- the content ratio of the ultraviolet absorber may be appropriately set according to the purpose, and is preferably 0.01 to 5 parts by weight, more preferably 0.1 to 1 part by weight with respect to 100 parts by weight of the total amount of the curable components. It is. When the content ratio is 0.01% by weight or more, the light resistance of the cured film can be improved, and when it is 5% by weight or less, the curability of the composition is excellent. be able to.
- Examples of the pigment / dye pigment include organic pigments and inorganic pigments.
- organic pigments include insoluble azo pigments such as toluidine red, toluidine maroon, Hansa Yellow, benzidine yellow and pyrazolone red; soluble azo pigments such as Ritol Red, Helio Bordeaux, Pigment Scarlet and Permanent Red 2B; Alizarin, Indantron And derivatives from vat dyes such as thioindigo maroon; phthalocyanine organic pigments such as phthalocyanine blue and phthalocyanine green; quinacridone organic pigments such as quinacridone red and quinacridone magenta; perylene organic pigments such as perylene red and perylene scarlet; Isoindolinone organic pigments such as indolinone yellow and isoindolinone orange; pyranthrone organic pigments such as pyranthrone red and pyranthrone orange Thioindigo organic pigments; condensed azo organic pigments;
- the inorganic pigment examples include titanium oxide, barium sulfate, calcium carbonate, zinc white, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, ultramarine blue, bitumen, and oxidation.
- examples include chrome green, cobalt green, amber, titanium black, and synthetic iron black.
- the carbon black exemplified as the filler can also be used as an inorganic pigment.
- Various conventionally known compounds can be used as the dye.
- Silane coupling agent A silane coupling agent is mix
- the silane coupling agent is not particularly limited as long as it can contribute to improvement in adhesion to the substrate.
- silane coupling agent examples include 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3- Glycidoxypropyltriethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N- (1,3-dimethyl-butylidene) propylamine, N-phenyl-3 -Aminopropyltrimethoxysilane, N
- the mixing ratio of the silane coupling agent may be appropriately set according to the purpose, and is preferably 0.1 to 10 parts by weight, more preferably 1 to 5 parts by weight with respect to 100 parts by weight of the total amount of the curable components. .
- the blending ratio is 0.1 parts by weight or more, the adhesive strength of the composition can be improved.
- the blending ratio is 10 parts by weight or less, it is possible to prevent the adhesive force from changing over time.
- composition of the present invention may be added with a surface modifying agent for the purpose of increasing the leveling property at the time of coating, the purpose of increasing the slipping property of the cured film and enhancing the scratch resistance, and the like.
- a surface modifying agent for the purpose of increasing the leveling property at the time of coating, the purpose of increasing the slipping property of the cured film and enhancing the scratch resistance, and the like.
- the surface modifier include a surface modifier, a surfactant, a leveling agent, an antifoaming agent, a slipperiness imparting agent, and an antifouling imparting agent, and these known surface modifiers can be used. . Of these, silicone-based surface modifiers and fluorine-based surface modifiers are preferred.
- silicone polymers and oligomers having a silicone chain and a polyalkylene oxide chain silicone polymers and oligomers having a silicone chain and a polyester chain
- fluorine polymers having a perfluoroalkyl group and a polyalkylene oxide chain a fluorine-based polymer and an oligomer having a perfluoroalkyl ether chain and a polyalkylene oxide chain.
- a surface modifier having an ethylenically unsaturated group, preferably a (meth) acryloyl group, in the molecule may be used.
- the content ratio of the surface modifier is preferably 0.01 to 1.0 part by weight with respect to 100 parts by weight of the total amount of the curable components. It is excellent in the surface smoothness of a coating film as it is the said range.
- the composition of the present invention may further contain a polymer for the purpose of further improving the curl resistance of the resulting cured film.
- Suitable polymers include (meth) acrylic polymers, and suitable constituent monomers include methyl (meth) acrylate, cyclohexyl (meth) acrylate, (meth) acrylic acid, glycidyl (meth) acrylate, N- ( 2- (meth) acryloxyethyl) tetrahydrophthalimide and the like.
- glycidyl (meth) acrylate may be added to introduce a (meth) acryloyl group into the polymer chain.
- the content ratio of the polymer is preferably 0.01 to 10 parts by weight with respect to 100 parts by weight of the total amount of the curable components. It is excellent in the curl resistance of the cured film obtained as it is the said range.
- composition for molding material Since the composition of the present invention has low viscosity and high hardness of the cured product, it can be preferably used as a composition for molding material.
- a microfabrication application such as nanoimprint is also referred to as a molding material for convenience.
- composition for molding materials contains said (A) as an essential component
- various components can be mix
- an antioxidant in addition to the components (B), (C), (D) and (E) described above, an antioxidant, an ultraviolet absorber, a pigment / dye, a silane coupling agent, a surface modification agent.
- examples include a quality agent, a polymer, and a polymerization inhibitor.
- Ink composition Since the composition of the present invention is excellent in thin film curability, it is suitable for color printing such as transparent overprint varnish ink and yellow, red, indigo, black ink, etc., which are further printed by a printing machine after single-color or multicolor printing. It can be preferably used for ink.
- Printing methods include offset printing (normal lithographic plates that use dampening water and waterless lithographic plates that do not use dampening water), relief printing (flat pressure relief printing, relief half-rotation, rotary rotation, intermittent rotation, flexo), and intaglio printing.
- Various printing methods such as (gravure printing), stencil printing (screen printing), ink jet printing and the like can be mentioned, and since it is excellent in emulsion stability, it can be preferably used for offset printing using fountain solution. Moreover, since it is low-viscosity, it can be preferably used as inkjet printing.
- the ink composition contains the component (A) as an essential component, but various components can be blended depending on the purpose.
- a method for producing an ink composition a conventional method for producing an ink composition may be followed.
- a binder hereinafter referred to as “(F) component”
- a pigment hereinafter referred to as “(G) component”.
- plasticizers and antifriction agents hereinafter, these components will be described.
- another component only 1 type of the illustrated compound may be used, and 2 or more types may be used together.
- (F) Component for example, a diallyl phthalate resin having no polymerizable group, such as an epoxy acrylate compound having at least one polymerizable group in one molecule, urethane acrylate And polyester acrylate.
- a diallyl phthalate resin having no polymerizable group such as an epoxy acrylate compound having at least one polymerizable group in one molecule, urethane acrylate And polyester acrylate.
- diallyl phthalate resin refers to a prepolymer synthesized from diallyl phthalate monomer or diallyl isophthalate monomer, and there are several commercially available products depending on the types and molecular weights of orthophthalic and isophthalic monomers. it can. Specific examples include Daiso Dup A, Daiso Dup S, Daiso Dup K, and Daiso Isodap sold by Daiso Corporation. Among these, Daiso Dup A is the most preferable among the above-mentioned commercial products in consideration of the film strength after ink curing, compatibility with the component (A), and the like.
- the content of the component (F) in the ink composition is preferably in the range of 10 to 65% by weight with respect to the total amount of the ink.
- the binder having a polymerizable group generally has a high viscosity. In the composition described in the examples, it becomes difficult to obtain a viscosity suitable as an offset ink.
- Component (G) examples of the pigment of component (G) include organic pigments and inorganic pigments.
- organic pigments include publicly known organic pigments for coloring, such as organic pigments for printing inks published in "Organic Pigment Handbook (Author: Isao Hashimoto, Publisher: Color Office, 2006 First Edition)" Soluble azo pigments, insoluble azo pigments, condensed azo pigments, metal phthalocyanine pigments, metal-free phthalocyanine pigments, quinacridone pigments, perylene pigments, perinone pigments, isoindolinone pigments, isoindoline pigments, dioxazine pigments, thioindigo pigments, anthra pigments Quinone pigments, quinophthalone pigments, metal complex pigments, diketopyrrolopyrrole pigments, carbon black pigments, and other polycyclic pigments can be used.
- inorganic pigments include titanium oxide, barium sulfate, calcium carbonate, zinc white, lead sulfate, yellow lead, zinc yellow, red bean curd (red iron (III) oxide), cadmium red, ultramarine blue, chromium oxide green, cobalt green. , Amber, titanium black, synthetic iron black, and carbon black.
- inorganic fine particles may be used as the extender pigment.
- inorganic fine particles inorganic coloring pigments such as titanium oxide, kraftite, zinc white; lime carbonate powder, precipitated calcium carbonate, gypsum, clay (ChinaClay), silica powder, diatomaceous earth, talc, kaolin, alumina white, barium sulfate, Inorganic pigments such as aluminum stearate, magnesium carbonate, barite powder, and abrasive powder; inorganic pigments such as silicone, glass beads, and the like.
- Plasticizers and anti-friction agents As plasticizers and anti-friction agents, paraffin wax, carnauba wax, beeswax, microcrystalline wax, polyethylene wax, oxidized polyethylene wax, polytetrafluoroethylene wax, amide wax and other wax compounds, palm oil Fatty acids in the range of about C8 to C18 such as fatty acids and soybean oil fatty acids can be blended and used within a range that does not interfere with the object of the present invention.
- Pattern Forming Composition The composition of the present invention can be preferably used as a pattern forming composition because it has high exposure sensitivity and is very excellent in developability and can form a precise and accurate pattern.
- composition for pattern formation has said (A) as an essential component
- various components can be mix
- specific examples of other components include the components (B), (D), (E), antioxidants, ultraviolet absorbers, silane coupling agents, surface modifiers and polymerization inhibitors, as well as alkalis.
- Soluble resin [hereinafter referred to as “component (H)”] and the like.
- component (H) will be described.
- another component only 1 type of the illustrated compound may be used, and 2 or more types may be used together.
- Component (H) acts as a binder for the component (A) and has a solubility in a developer used in the development processing step, particularly preferably an alkali developer. If it is, it will not specifically limit.
- a developer used in the development processing step particularly preferably an alkali developer.
- the component (H) include addition polymers, polyesters, epoxy resins, and polyethers, and addition polymers obtained by polymerizing ethylenically unsaturated monomers are preferred.
- an alkali-soluble resin having a carboxyl group is preferable, and in particular, an ethylenically unsaturated monomer having one or more carboxyl groups (hereinafter referred to as “carboxyl group-containing unsaturated monomer”) and this A copolymer (hereinafter referred to as “carboxyl group-containing copolymer”) with an ethylenically unsaturated monomer copolymerizable with (hereinafter referred to as “copolymerizable unsaturated monomer”) is preferred.
- carboxyl group-containing unsaturated monomer examples include unsaturated monocarboxylic acids such as (meth) acrylic acid, crotonic acid, ⁇ -chloroacrylic acid and cinnamic acid; maleic acid, maleic anhydride, fumaric acid, itacone Unsaturated dicarboxylic acids or anhydrides thereof such as acid, itaconic anhydride, citraconic acid, citraconic anhydride and mesaconic acid; trivalent or higher unsaturated polycarboxylic acids or anhydrides thereof; succinic acid mono (2- ( Mono [(meth) acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids such as (meth) acryloyloxyethyl) and phthalic acid mono (2- (meth) acryloyloxyethyl); and ⁇ -carboxy Examples include mono (meth) acrylates of polymers having a carboxy group and a hydroxyl group at both ends,
- succinic acid mono (2-acryloyloxyethyl) and phthalic acid mono (2-acryloyloxyethyl) are Aronix M-5300 and M-5400 [Toagosei Co., Ltd., respectively. It is commercially available under the trade name of “Co., Ltd.”.
- the carboxyl group-containing unsaturated monomers can be used alone or in admixture of two or more.
- the copolymerizable unsaturated monomer may be any copolymerizable with a carboxyl group-containing unsaturated monomer, such as an aromatic vinyl compound, an unsaturated carboxylic acid ester, an unsaturated imide, and a terminal. Macromonomers having a mono (meth) acryloyl group are preferred.
- aromatic vinyl compounds examples include styrene, ⁇ -methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, 2 -Vinyl benzyl methyl ether, 3-vinyl benzyl methyl ether, 4-vinyl benzyl methyl ether, 2-vinyl benzyl glycidyl ether, 3-vinyl benzyl glycidyl ether, 4-vinyl benzyl glycidyl ether and the like.
- Unsaturated carboxylic acid esters include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, sec -Butyl (meth) acrylate, t-butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate , 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl (meth) acrylate 2-methoxyethyl (
- unsaturated imides examples include maleimide, N-phenylmaleimide and N-cyclohexylmaleimide.
- macromonomers having a mono (meth) acryloyl group at the terminal include those having a polymer molecular chain such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate and polysiloxane. it can.
- copolymerizable unsaturated monomer in addition to the above, 2- (3,4,5,6-tetrahydrophthalimido) ethyl (meth) acrylate, 2- (2,3-dimethylmaleimido) ethyl (meth) Imide (meth) acrylates such as acrylate; 2-aminoethyl (meth) acrylate, 2-dimethylaminoethyl (meth) acrylate, 2-aminopropyl (meth) acrylate, 2-dimethylaminopropyl acrylate, 3-aminopropyl ( Unsaturated carboxylic acid aminoalkyl esters such as meth) acrylate and 3-dimethylaminopropyl (meth) acrylate; unsaturated carboxylic acid glycidyl esters such as glycidyl (meth) acrylate; indene such as indene and 1-methylindene; Vinyl acetate, vinyl propionate
- (meth) acrylic acid is an essential component, and in some cases, from the group of succinic acid mono (2- (meth) acryloyloxyethyl) and ⁇ -carboxypolycaprolactone mono (meth) acrylate.
- a carboxyl group-containing unsaturated monomer component further containing at least one selected compound, and styrene, methyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, allyl (meth) acrylate, and benzyl (meth) acrylate ,
- carboxyl group-containing copolymer ( ⁇ ) examples include (meth) acrylic acid / methyl (meth) acrylate copolymer, (meth) acrylic acid / benzyl (meth) acrylate copolymer, (meth) acrylic acid.
- the copolymerization ratio of the carboxyl group-containing unsaturated monomer in the carboxyl group-containing copolymer is usually 5 to 50% by weight, preferably 10 to 40% by weight.
- the solubility of the resulting composition in an alkaline developer can be improved, while when the copolymerization ratio is 50% by weight or less, the solubility in the alkaline developer is increased. Therefore, when developing with an alkali developer, the spacer layer and the pixel can be prevented from falling off the substrate and the spacer surface can be prevented from being rough.
- an alkali-soluble resin having an ethylenically unsaturated group in the side chain improves the crosslinking density of the resulting cured film, and improves the coating strength, heat resistance, and chemical resistance. Since it becomes the thing excellent in the point, it is preferable.
- the alkali-soluble resin having an ethylenically unsaturated group in the side chain is preferably an alkali-soluble resin having a carboxyl group.
- the resin include those obtained by adding an unsaturated compound having an epoxy group (hereinafter referred to as “epoxy unsaturated compound”) to the carboxyl group-containing copolymer.
- the epoxy unsaturated compound examples include epoxy group-containing (meth) acrylates such as glycidyl (meth) acrylate and cyclohexene oxide-containing (meth) acrylate.
- epoxy group-containing (meth) acrylates such as glycidyl (meth) acrylate and cyclohexene oxide-containing (meth) acrylate.
- a method for the addition reaction a conventional method may be followed, and it can be produced by adding an epoxy unsaturated compound to a carboxyl group-containing copolymer in an organic solvent or without a solvent.
- the reaction temperature, reaction time, and catalyst may be appropriately selected according to each reaction.
- the Mw of the component (H) is preferably 3,000 to 300,000, more preferably 5,000 to 100,000.
- the number average molecular weight (hereinafter referred to as “Mn”) is preferably 3,000 to 60,000, more preferably 5,000 to 25,000.
- Mw and Mn mean values obtained by converting the molecular weight measured by GPC (elution solvent: tetrahydrofuran) into polystyrene.
- GPC elution solvent: tetrahydrofuran
- the ratio (Mw / Mn) of Mw and Mn of the component (H) is usually 1 to 5, preferably 1 to 4.
- a component can be used individually or in combination of 2 or more types.
- the proportion of the component (A) and the component (H) is preferably 10 to 100% by weight of the component (A) and 0 to 90% by weight of the component (H) based on the total amount of these components, and more preferably the component (A). 20 to 100% by weight and (H) component 0 to 80% by weight. If the proportion of the component (H) is less than 10% by weight, the crosslinking density is lowered, so that the coating film strength, heat resistance and chemical resistance tend to be lowered.
- the proportion of the component (A) and the component (H) in the composition is preferably 10 to 50% by weight in the composition as the total amount of the component (A) and the component (H).
- a conventional method may be followed. For example, after apply
- component photopolymerization initiator
- component thermal polymerization initiator
- the substrate to which the composition of the present invention can be applied is applicable to various materials, and examples thereof include plastic, wood, metal, inorganic material, and paper.
- plastics include cellulose acetate resins such as polyvinyl alcohol, triacetyl cellulose and diacetyl cellulose, cyclic polyolefin resins having cyclic olefins such as acrylic resin, polyethylene terephthalate, polycarbonate, polyarylate, polyethersulfone, norbornene as monomers. , Polyvinyl chloride, epoxy resin, polyurethane resin and the like.
- the wood include natural wood and synthetic wood.
- the metal examples include steel plates, metals such as aluminum and chromium, and metal oxides such as zinc oxide (ZnO) and indium tin oxide (ITO).
- metal oxides such as zinc oxide (ZnO) and indium tin oxide (ITO).
- inorganic materials include glass, mortar, concrete, and stone. Among these, a plastic substrate is particularly preferable.
- the thickness of the cured film may be selected according to the use of the substrate to be used and the substrate having the produced cured film, but is preferably 1 to 500 ⁇ m, more preferably 5 to 200 ⁇ m. .
- the method of applying the composition of the present invention to the substrate may be appropriately set according to the purpose, and is a bar coater, applicator, doctor blade, dip coater, roll coater, spin coater, flow coater, knife coater, comma.
- the coating method include a coater, a reverse roll coater, a die coater, a lip coater, a gravure coater, a micro gravure coater, and an ink jet.
- Examples of the active energy ray for curing the composition of the present invention include ultraviolet rays, visible rays, and electron beams, and ultraviolet rays are preferred.
- Examples of the ultraviolet irradiation device include a high pressure mercury lamp, a metal halide lamp, an ultraviolet (UV) electrodeless lamp, and a light emitting diode (LED).
- the irradiation energy may be appropriately set according to the type and composition of the active energy ray. As an example, when a high-pressure mercury lamp is used, the irradiation energy in the UV-A region is 10 0 to 5,000 mJ / cm 2 is preferable, and 200 to 1,000 mJ / cm 2 is more preferable.
- a method for using the composition of the present invention for molding material application a conventional method may be used. Specifically, the composition is applied to a mold called a stamper having a desired shape and laminated with a film or sheet base material (hereinafter collectively referred to as “film base material”), and then the active energy.
- film base material a film or sheet base material
- a method of curing by irradiating a line, a method of curing by irradiating an active energy ray after injecting the composition into a predetermined mold, and a thermosetting type composition In some cases, a method of heating and curing may be used.
- film substrates examples include polymethyl methacrylate, polymethyl methacrylate-styrene copolymer film, polyethylene terephthalate, polyethylene naphthalate, polyarylate, polyacrylonitrile, polycarbonate, polysulfone, polyethersulfone, and polyetherimide.
- Plastic films such as polyetherketone, polyimide, and polymethylpentene are preferable. If necessary, a glass-based substrate can be used.
- the film substrate is preferably transparent or translucent (for example, milky white).
- the thickness of the film substrate is preferably 20 to 500 ⁇ m.
- Examples of the active energy ray for curing the composition of the present invention include ultraviolet rays, visible rays, and electron beams, and ultraviolet rays are preferred.
- Examples of the ultraviolet irradiation device include the same devices as described above.
- the irradiation energy may be appropriately set according to the type of active energy ray and the composition of the active energy ray, and examples include the same irradiation energy as described above.
- the composition of the present invention is poured between a mold having a target lens shape and a transparent substrate.
- active energy rays are irradiated from the transparent substrate side to cure the composition, and then the mold is removed.
- the material of the mold is not particularly limited, and examples thereof include metals such as brass and nickel, and resins such as epoxy resins. It is preferable that the mold is made of metal in view of the long life of the mold.
- the composition of the present invention When the composition of the present invention is used for nanoimprint applications, it may be in accordance with a conventional method. For example, after applying the composition to a substrate, a mold (mold) having a microfabricated pattern and having transparency is pressed. Next, a method of curing the composition by irradiating active energy rays from a transparent mold, and then demolding the mold can be used.
- the printing substrate used in the printed material of the present invention is not particularly limited.
- paper such as fine paper, coated paper, art paper, imitation paper, thin paper, cardboard, various synthetic papers, Polyester resin, acrylic resin, vinyl chloride resin, vinylidene chloride resin, polyvinyl alcohol, polyethylene, polypropylene, polyacrylonitrile, ethylene vinyl acetate copolymer, ethylene vinyl alcohol copolymer, ethylene methacrylic acid copolymer, nylon, polylactic acid,
- films and sheets such as polycarbonate, cellophane, aluminum foil, and other various base materials conventionally used as printing base materials.
- a paper base material is particularly preferable.
- the thickness of the cured film may be selected according to the use of the substrate to be used and the substrate having the produced cured film, but is preferably 1 to 20 ⁇ m, more preferably 1 to 10 ⁇ m. .
- composition of the present invention When used for offset ink, it can be suitably used as an application method to a base material by using an offset printing machine that continuously supplies water onto a printing plate. Further, the present invention can be suitably used in any sheet feeding method, such as a sheet-fed offset printing machine using sheet-type printing paper, an offset rotary printing machine using reel-type printing paper.
- composition of the present invention when used for inkjet ink, it can be suitably used as a coating method on a substrate by using a known inkjet recording apparatus or the like that forms an image by discharging by an inkjet method. .
- the viscosity of the composition is 7 mPa ⁇ s to 30 mPa ⁇ s at the temperature at the time of discharge (for example, 40 ° C. to 80 ° C., preferably 25 ° C. to 30 ° C.) in consideration of discharge properties. preferable. More preferably, it is 7 mPa ⁇ s to 20 mPa ⁇ s.
- Examples of the active energy ray for curing the composition of the present invention include ultraviolet rays, visible rays, and electron beams, and ultraviolet rays are preferred.
- Examples of the ultraviolet irradiation device include the same devices as described above.
- the irradiation energy may be appropriately set according to the type of active energy ray and the composition of the active energy ray, and examples include the same irradiation energy as described above.
- pattern forming composition photosensitive lithographic printing plates, resists such as etching resists and solder resists, columnar spacers in the manufacture of liquid crystal panels, pixels and black matrices in color filters, etc. For example, and a color filter protective film.
- the composition of the present invention can be preferably used depending on the use of column spacers, coloring compositions for color filters, and protective films for color filters in liquid crystal panel production.
- nonionic surfactants such as polyoxyethylene lauryl ether and fluorine-based surfactants are added to the composition in order to improve coatability and developability. It can also be added.
- spacer the use of the columnar spacer (hereinafter simply referred to as “spacer”) and the coloring composition will be described.
- the spacer is formed of a photocured coating film of the composition by a photolithography method.
- the spacer can be formed in an arbitrary size at an arbitrary position on the liquid crystal panel substrate. In general, the spacer is often formed on a black matrix region which is a light shielding portion of a color filter or on a TFT electrode.
- the spacer may be formed by a conventional method.
- the composition of the present invention is applied on a substrate such as glass to a film thickness necessary for forming a cell gap, and then heated (hereinafter referred to as “pre-baking”), and drying the coating film, followed by exposure, development, and post-heating (hereinafter abbreviated as “post-baking”) steps.
- the composition When the composition is applied on the substrate, it is applied slightly thicker than the design value of the cell gap in consideration of film reduction or deformation due to development, post-baking or the like. Specifically, it is preferable that the film thickness after pre-baking is 5 to 10 ⁇ m, more preferably 6 to 7 ⁇ m.
- the coating method include a printing method, a spray method, a roll coating method, a bar coating method, a curtain coating method, a spin coating method, a die coating method (slit coating method), etc., and generally a spin coating method or a die coating method. Use the law.
- pre-baking is performed.
- the temperature and time are 50 to 150 ° C. and about 5 to 15 minutes.
- the pre-baked coating surface is irradiated with light through a mask having a predetermined pattern shape for forming a spacer.
- the light to be used is preferably ultraviolet light or visible light, and light having a wavelength of 240 nm to 410 nm obtained from a high pressure mercury lamp, a metal halide lamp or the like is used.
- the light irradiation conditions depend on the type of light source, the absorption wavelength of the photopolymerization initiator to be used, the film thickness of the coating film, and the like, but it is preferable that the light irradiation amount be approximately 50 to 600 mJ / cm 2 .
- the light irradiation amount is less than 50 mJ / cm 2 , the curing is poor and the exposed part is easily dropped during development. On the other hand, if the light irradiation amount is more than 600 mJ / cm 2 , a fine spacer pattern tends to be difficult to obtain. .
- a developer As the developer, an aqueous solution of an alkali compound can be used.
- the alkaline compound include potassium hydroxide, sodium hydroxide, sodium carbonate, sodium hydrogen carbonate, sodium silicate, ammonia, tetramethylammonium hydroxide, and the like.
- water-soluble organic solvents such as methanol, ethanol, isopropanol and benzyl alcohol, and various surfactants may be added to the developer.
- the developing method may be any of a liquid piling method, a dipping method, a spray method, and the like. After development, the pattern portion is washed with water for 0.5 to 1.5 minutes and air-dried with compressed air or the like to obtain a spacer pattern.
- the obtained spacer pattern is post-baked in a temperature range of 150 to 350 ° C. with a heating device such as a hot plate or oven to obtain the liquid crystal panel spacer of the present invention.
- a heating device such as a hot plate or oven
- the thickness of the spacer varies depending on the cell gap setting value of the liquid crystal panel, but is designed to be approximately 3 to 5 ⁇ m after post-baking.
- Coloring composition When the composition of the present invention is used as a coloring composition, a pigment and a pigment dispersant are further blended. Hereinafter, these components will be described.
- the pigment is not particularly limited, and various organic or inorganic pigments can be used.
- organic pigments in addition to those described above, more specifically, compounds classified as pigments in the color index (CI; issued by The Society of Dyers and Colorists), that is, as follows The color index (CI) number is attached.
- Pigment Yellow 185 I. Pigment red 1, C.I. I. Pigment red 2, C.I. I. Pigment red 3, C.I. I. Pigment red 177, C.I. I. Red pigments such as CI Pigment Red 254; and C.I. I. Pigment blue 15, C.I. I. Pigment blue 15: 3, C.I. I. Pigment blue 15: 4, C.I. I. C.I. Blue pigments such as CI Pigment Blue 15: 6; I. Pigment green 7, C.I. I. Green pigments such as C.I. Pigment Green 36; I. Pigment violet 23, C.I. I. Pigment violet 23:19 and the like.
- phthalocyanines with high bromination rates such as Monastral Green 6YC and 9YC (manufactured by Avicia Co., Ltd.), which have been difficult to disperse in the past, high brightness G pigments, metals whose central metal is other than copper, such as Mg, Al, Si , Ti, V, Mn, Fe, Co, Ni, Zn, Ge, Sn, etc., high color purity G pigments made of different metal phthalocyanine pigments can be used.
- inorganic pigment examples include those described above.
- a pigment can be used individually or in mixture of 2 or more types.
- the pigment dispersion can impart excellent dispersibility to various pigments widely used in color filters for liquid crystal display devices among these pigments.
- It can be suitably used when preparing a pigment dispersion containing at least one selected from the group consisting of CI Pigment Yellow 139, the phthalocyanine pigment having a high bromination rate, and the dissimilar metal phthalocyanine pigment.
- the pigment dispersant is not particularly limited, and various pigment dispersants can be used.
- Specific examples of usable pigment dispersants include amide compounds such as nonanoamide, decanamide, dodecanamide, N-dodecylhexamide, N-octadecylpropioamide, N, N-dimethyldodecanamide and N, N-dihexylacetamide.
- Amine compounds such as diethylamine, diheptylamine, dibutylhexadecylamine, N, N, N ′, N′-tetramethylmethanamine, triethylamine, tributylamine and trioctylamine, monoethanolamine, diethanolamine, triethanolamine, N, N, N ′, N ′-(tetrahydroxyethyl) -1,2-diaminoethane, N, N, N′-tri (hydroxyethyl) -1,2-diaminoethane, N, N, N ′, N'-tetra (hydroxyethylpolyoxyethylene) -1,2 -Amines having a hydroxy group such as diaminoethane, 1,4-bis (2-hydroxyethyl) piperazine and 1- (2-hydroxyethyl) piperazine, etc., and other examples include nipecotamide, isonipecotamide, nicotinamide And the like
- (co) polymers of unsaturated carboxylic acid esters such as polyacrylic acid esters; (partial) amine salts, (partial) ammonium salts of (co) polymers of unsaturated carboxylic acid esters such as polyacrylic acid (Partial) alkylamine salts; (co) polymers of hydroxyl group-containing unsaturated carboxylic acid esters such as hydroxyl group-containing polyacrylic acid esters and their modified products; polyurethanes; unsaturated polyamides; polysiloxanes; long-chain polyaminoamides Phosphate salts: Amides obtained by reacting poly (lower alkyleneimine) with free carboxyl group-containing polyesters and salts thereof can be mentioned.
- Shigenox-105 (trade name, manufactured by Hakkol Chemical), Disperbyk-101, -130, -140, -170, -171, -182, -2001 [Above, manufactured by Big Chemie Japan Co., Ltd.], EFKA-49, -4010, -9900 (above, EFKA CHEMICALS), Solsperse 12000, 13240, 13940, 17000, 20000, 24000GR, 24000SC, 27000, 28000, 33500 [above, manufactured by Zeneca Co., Ltd.], PB821, 822 [above, manufactured by Ajinomoto Co., Inc.], and the like.
- the pigment dispersant is preferably used in an amount of 10 to 90 parts by weight, more preferably 20 to 80 parts by weight, based on 100 parts by weight of the pigment.
- the coloring composition may further contain an ultraviolet blocking agent, an ultraviolet absorber, a surface conditioner (leveling agent), and other components.
- the coloring composition is manufactured by directly mixing the component (A), the pigment, the pigment dispersant, and other components as required, into the component (E) (organic solvent) and dispersing the mixture using a known disperser.
- component (E) organic solvent
- a method of preparing a pigment dispersion in advance is preferable.
- a photosensitive coloring composition excellent in pigment dispersibility can be easily obtained.
- a pigment, a pigment dispersant, and a solvent for dispersing a part of the component (F) as necessary hereinafter referred to as “dispersing solvent”.
- a pigment dispersion is prepared in advance by mixing and dispersing.
- the (A) component and, if necessary, the (F) component and other components are mixed in a solvent for diluting (hereinafter referred to as “diluting solvent”) and dissolved or dispersed to form a clear resist.
- diluting hereinafter referred to as “diluting solvent”
- the coloring composition excellent in pigment dispersibility is easily obtained by mixing the obtained pigment dispersion liquid and a clear resist liquid, and performing a dispersion process as needed. According to this method, since the dispersion solvent and the diluting solvent can be selected separately, the range of solvent selection is expanded.
- the pigment dispersion is not pre-prepared, first add the pigment, pigment dispersant, and, if necessary, the alkali-soluble resin to the organic solvent, and mix and stir to disperse the pigment.
- the pigment dispersibility is not inhibited by the other compounding components in the pigment dispersion step, and the stability is also excellent.
- the colored composition thus obtained is applied to a support to form a coating film, dried, and then a part of the coating film is selected by irradiating the coating film with light in a predetermined pattern. After being cured, the film is developed with an alkaline solution, post-baked, and further heat-cured to obtain a colored coating film having a predetermined pattern.
- the light to be used is preferably ultraviolet light or visible light, and light having a wavelength of 240 nm to 410 nm obtained from a high pressure mercury lamp, a metal halide lamp or the like is used.
- the irradiation energy required for curing is usually about 10 to 500 mJ / cm 2 .
- a predetermined position of the coating film can be selectively exposed and cured by irradiating the surface of the coating film with laser light or irradiating light through a mask.
- heat curing is usually performed by drying at 50 to 200 ° C. using a vacuum dryer, oven, hot plate, or other device to which heat is applied, and then heating and curing at a temperature of about 120 to 250 ° C. .
- the cured part in the coating film has a structure in which the pigment is uniformly dispersed in the matrix formed by the cross-linking network formed by the photocuring reaction and the thermosetting reaction according to the present invention. .
- This colored composition is excellent in curability, has an increased crosslink density and hardens uniformly to the inside, so that it is difficult to reverse taper during development, and a pattern with a forward taper shape, sharp edges and good surface smoothness is formed.
- the colored composition of the present invention can provide a colored cured film having high electrical reliability because impurities are confined in a matrix having a high crosslinking density that is hardened to the inside during curing and is not easily eluted into the liquid crystal layer.
- the voltage of the display portion can be stably maintained and electric reliability is high.
- the colored composition can disperse a high concentration pigment finely and uniformly, and has high colorability. Therefore, even if it is thin, it can form a colored pattern having a large color concentration, and has a wide color reproduction range. .
- the colored composition can be used to form various colored coatings, and is particularly suitable for forming a colored layer constituting the details of a color filter, that is, a pixel or a black matrix.
- parts means parts by weight.
- Production Example 1 Production of DGLY-TA by transesterification method
- a 1 liter flask equipped with a stirrer, thermometer, gas introduction tube, rectification column and cooling tube 77.00 parts (0.46 mol) of diglycerin and 627.21 parts of 2-methoxyethyl acrylate ( 4.82 mol), 2.45 parts (0.02 mol) of DABCO as catalyst X, 4.00 parts (0.02 mol) of zinc acetate as catalyst Y, and 1.42 parts of hydroquinone monomethyl ether (charged) (2000 wtppm with respect to the total weight of the raw materials), and oxygen-containing gas (5% by volume of oxygen and 95% by volume of nitrogen) was bubbled into the liquid.
- the pressure in the reaction system is adjusted within the range of 110 to 760 mmHg, and 2-methoxyethanol and 2-methoxyethyl acrylate by-produced as the transesterification proceeds.
- 2-methoxyethyl acrylate in the same weight part as the extracted liquid was added to the reaction system as needed. 27 hours after the start of heating and stirring, the pressure in the reaction system was returned to normal pressure, and the extraction was completed.
- the reaction solution was cooled to room temperature, 200 ml of normal hexane was added, and the precipitate was separated by filtration.
- the reaction system was stirred while being heated to reflux at a pressure of 370 mmHg, and water produced as a by-product with the progress of the dehydration esterification reaction was withdrawn from the reaction system via a rectification column and a cooling tube. During this time, the temperature of the reaction liquid changed in the range of 80 to 90 ° C. After 5 hours from the start of heating and stirring, the heating of the reaction solution was completed, and the pressure in the reaction system was returned to normal pressure to complete the extraction. After cooling the reaction solution to room temperature, 133 parts of toluene and 61 parts of water were added and stirred, and then allowed to stand to separate the lower layer (aqueous layer).
- Comparative Production Example 3 (Production of polyfunctional acrylate by dehydration ester method) A polyfunctional acrylate was produced in the same manner as in Comparative Production Example 1 except that the compounds shown in Table 2 below were used as the polyhydric alcohol and the catalyst. The results are shown in Table 3.
- reaction solution B solid content concentration 31.5%
- the weight average molecular weight (Mw) of this alkali-soluble resin (h1) was 7,400, and the acid value was 76 mgKOH / g (solid content conversion).
- Viscosity The viscosity of the purified product obtained was measured with an E-type viscometer (25 ° C. or 50 ° C.).
- Emulsification resistance 3 g of the purified product thus obtained was dissolved in 6 g of xylene, and 9 g of distilled water was put into a glass test tube (18 m ⁇ hard glass) and stoppered. This was shaken up and down 10 times to emulsify, and then allowed to stand to measure the time until the water layer and the organic layer were completely separated, and the transparency of the upper layer and the lower layer was evaluated according to the following criteria. There is a correlation between water separability and emulsification resistance. The better the water separability, the better the emulsification resistance when applied to ink. A: Transparent. ⁇ : Slightly cloudy ⁇ : Cloudy ⁇ : Milky
- the metal ion concentration in the product is measured by the calibration curve method. To 1 g of sample, add 9 ml of methanol and measure by the flame method. There is a correlation between the metal ion concentration in the polyfunctional acrylate and the electrical characteristics. By reducing the metal ion concentration in the polyfunctional acrylate, migration of metal ions can be suppressed when a device using this is formed. it can.
- Comparative Production Example 1 is an example of a polyfunctional acrylate obtained by a transesterification reaction using a phosphine compound as the catalyst X, but there are no problems with viscosity, emulsification, and ion elution. There was a problem in storage stability.
- Comparative Production Examples 2 and 3 are compositions containing components produced by the conventional dehydration ester method and having a high molecular weight area of 30% or more, so the viscosity is high and the emulsification resistance is poor. .
- the metal ion concentration is high, and there is a concern that the electric characteristics may be deteriorated due to ion elution from the cured film.
- Example 7 and 8 and Comparative Examples 7 and 8 the coating film was dried on a hot plate at 100 ° C. for 3 minutes to form a coating film having a dry film thickness of 5 ⁇ m.
- the number of passes until the surface tack was eliminated was determined.
- Emulsification resistance evaluation as an active energy ray-curable composition for ink
- the compositions described in Table 6 below were also evaluated in the same manner as the emulsion resistance method.
- the evaluation results were the same as those in Table 4.
- alkali developability evaluation as a pattern forming the active energy ray-curable composition
- the composition described in Table 7 below was applied on a 10 cm square chromium mask glass substrate by a spin coater, and this coating film was dried on a hot plate at 100 ° C. for 3 minutes to form a coating film having a dry film thickness of 5 ⁇ m. did.
- the obtained coating film was spray-developed with a 0.05% aqueous potassium hydroxide solution having a liquid temperature of 23 ° C., and the time until complete dissolution was measured.
- the composition of the present invention exhibits the same curability as the compositions of Comparative Examples 1 and 2 containing a polyfunctional acrylate produced by the conventional dehydrating ester method. Since the area% of the high molecular weight component (A) was less than 30%, the cured film was excellent in hardness.
- the compositions of Comparative Examples 1 and 2 containing the components produced by the conventional dehydrated ester method are compositions in which the polyfunctional acrylate contains 30% by area or more of the high molecular weight substance. The cured film was inferior in hardness to the product.
- the composition of the present invention has the same curability as the ink compositions of Comparative Examples 3 and 4 containing a polyfunctional acrylate produced by the conventional dehydrating ester method. showed that.
- the ink composition is also excellent in emulsification resistance and is suitable as an ink composition.
- the ink compositions of Comparative Examples 3 and 4 were poor in emulsification resistance of the starting polyfunctional acrylate, so that the ink composition also had poor emulsification resistance and was not suitable for ink use.
- the composition of the present invention has a curability equivalent to that of the pattern forming compositions of Comparative Examples 5 and 6 containing the components produced by the conventional dehydrating ester method. As shown, the alkali developability was further superior to the compositions of Comparative Examples 5 and 6. Furthermore, as described above, since the component (A) has a low metal ion concentration, the component (A) was suitable as a pattern-forming composition that is not concerned with a decrease in electrical characteristics.
- composition of the present invention can be used for various coating applications such as hard coating, molding materials used in mold transfer and nanoimprinting, ink applications such as offset and ink jet printing, and resist applications such as photosensitive lithographic printing plates and color resists. It can be used for various coating applications such as hard coating, molding materials used in mold transfer and nanoimprinting, ink applications such as offset and ink jet printing, and resist applications such as photosensitive lithographic printing plates and color resists. It can be used for various coating applications such as hard coating, molding materials used in mold transfer and nanoimprinting, ink applications such as offset and ink jet printing, and resist applications such as photosensitive lithographic printing plates and color resists. It can be used for various coating applications such as hard coating, molding materials used in mold transfer and nanoimprinting, ink applications such as offset and ink jet printing, and resist applications such as photosensitive lithographic printing plates and color resists. It can be used for various coating applications such as hard coating, molding materials used in mold transfer and nanoimprinting, ink applications such as offset and ink
Abstract
Description
尚、本明細書においては、アクリロイル基及び/又はメタクリロイル基を(メタ)アクリロイル基と表し、アクリレート及び/又はメタクリレートを(メタ)アクリレートと表し、アクリル酸及び/又はメタクリル酸を(メタ)アクリル酸と表す。
DPHAは高粘度であり、PETTAは常温で固体であるため、組成物の無溶剤化が難しい。特許文献2には、DPHAを低粘度化するために、1個の(メタ)アクリロイル基を有する化合物(以下、「単官能(メタ)アクリレート」という)や2個の(メタ)アクリロイル基を有する化合物(以下、「2官能(メタ)アクリレート」という)を30重量部以上含む活性エネルギー線硬化型組成物が開示されている。
しかしながら、特許文献2の組成物は、プラスチックフィルム上に形成した硬化膜の硬度が低すぎるという問題がある。
又、DPHA及びPETTAは、通常、多価アルコールとアクリル酸の脱水エステル化により製造されているが、これら製品中には高分子量体を含んでいるため、硬化膜の硬度低下の一因となっており、硬度の向上が求められている。
DPHA及びPETTAは、前記した通り脱水エステル化により製造したものであるため、製品中には高分子量体を含んでおり、乳化安定性低下の一因となる。
特許文献4では、未反応のアクリル酸を除去する工程に引続き、特定の溶剤と水の混合物により洗浄することで水溶性成分を除去し、乳化安定性が改善できることが開示されている。
しかしながら、廃溶剤及び廃液が増えるため、この方法に替わる、高分子量体を低減可能な製造方法が求められている。
DPHA又はPETTAは、前記した通り脱水エステル化により製造したものであるため、未反応のアクリル酸を除去する工程で使用するアルカリ金属水溶液由来のアルカリ金属イオンが製品中に1ppm以上残存しており、硬化膜からの金属イオン溶出による電気特性の低下が問題となることがある。
特許文献6においては、基板と硬化膜の密着性を向上させることで金属イオンの溶出を抑え、液晶表示装置に用いた場合に液晶の比抵抗を良好にすることが開示されている。
しかしながら、その性能は不充分であり、DPHA又はPETTA中の金属イオン量を根本的に低減することが求められている。
しかしながら、DGLY-TA及びGLY-TAを、それぞれジグリセリン及びグリセリンとアクリル酸の脱水エステル化により製すると、特に、2級水酸基の反応性が低く、製品を得ることが困難であり、現在市場には流通していない。
高分子量体の生成を抑制する(メタ)アクリレートの製造方法として、スズ触媒又はチタン触媒を用いたエステル交換法が知られている(特許文献10、11)。
しかしながら、従来のエステル交換反応では、3個以上のアルコール性水酸基を有する多価アルコールを原料とした場合、長時間反応させても反応率が低いため、理想構造(メタ)アクリレート濃度が低く、硬化膜の硬度が低いという問題があった。
一方、ホスフィン系触媒を用いたエステル交換法が知られており、多官能(メタ)アクリレートの製造方法として触媒活性に優れるものであった(特許文献12)。
しかしながら、本発明者らの検討によれば、反応終了後に反応液中存在するホスフィン系触媒は、ろ過及び吸着等による簡便な方法により反応液から除去し難いという製造上の問題を有するものであった。このため、最終製品中にもホスフィン系触媒が残存してしまい、これにより製品の保存中に、濁りや触媒の析出が発生したり、経時的に増粘又はゲル化してしまうという保存安定性の問題を生じるものであり、組成物の成分として使用する場合も同様の問題を有するものであった。
以下、本発明を詳細に説明する。
触媒X:アザビシクロ構造を有する環状3級アミン又はその塩若しくは錯体、アミジン又はその塩若しくはその錯体、並びにピリジン環を有する化合物又はその塩若しくは錯体からなる群から選ばれる一種以上の化合物。
触媒Y:亜鉛を含む化合物。
以下、(A)成分、その他の成分及び使用方法について説明する。
(A)成分は、前記触媒X及びYの存在下に、多価アルコール(ジグリセリン又は/及びグリセリン)と単官能(メタ)アクリレートをエステル交換反応させて得られる多官能(メタ)アクリレートの混合物である。
前記触媒X及びYを併用する多価アルコールと単官能(メタ)アクリレートのエステル交換反応によれば、多価アルコールと(メタ)アクリル酸を脱水エステル化反応と比較して、(A)成分中の高分子量体が少ないために低粘度で不純物が少なく、このため前記物性に優れる多官能(メタ)アクリレート混合物を製造することが可能となる。
以下、多価アルコール、単官能(メタ)アクリレート、触媒X、触媒Y及び(A)成分の製造方法について説明する。
本願発明では、(A)成分原料としてジグリセリン又は/及びグリセリンを使用する。
ジグリセリン又は/及びグリセリンは、得られる(A)成分の硬化膜の硬度が高いという点で好ましい。
その他多価アルコールを併用する場合の割合としては、ジグリセリン又は/及びグリセリンの合計100重量部に対して、50重量部以下が好ましい。
(A)成分の原料として使用する単官能(メタ)アクリレートは、分子中に1個の(メタ)アクリロイル基を有する化合物であり、例えば、下記一般式(1)で示される化合物が挙げられる。
R2としては、これら官能基の中でも、メチル基、エチル基、プロピル基、ペンチル基、ブチル基、へプチル基、オクチル基、へプチル基及び2-エチルヘキシル基等の炭素数1~8のアルキル基、メトキシエチル基、エトキシエチル基及びメトキシブチル基等のアルコキシアルキル基、N,N-ジメチルアミノエチル基、N,N-ジエチルアミノエチル基、N,N-ジメチルアミノプロピル基、N,N-ジエチルアミノプロピル基等のジアルキルアミノ基が好ましい。
これらの単官能(メタ)アクリレートの中では、メチル(メタ)アクリレート、エチル(メタ)アクリレート、n-ブチル(メタ)アクリレート及びi-ブチル(メタ)アクリレート及び2-エチルヘキシル(メタ)アクリレート等の炭素数1~8のアルキル基を有するアルキル(メタ)アクリレート、2-メトキシエチルアクリレート等のアルコキシアルキル(メタ)アクリレート、並びにN,N-ジメチルアミノエチル(メタ)アクリレートが好ましく、特に殆どの多価アルコールに対して良好な反応性を示し、入手が容易な炭素数1~4のアルキル基を有する(メタ)アクリレート、及び炭素数1~2のアルキル基を有するアルコキシアルキル(メタ)アクリレートが好ましい。
さらに、多価アルコールの溶解を促進し、極めて良好な反応性を示す炭素数1~2のアルキル基を有するアルコキシアルキル(メタ)アクリレートがより好ましく、2-メトキシエチル(メタ)アクリレートが特に好ましい。
さらに又、単官能(メタ)アクリレートとしては、アクリレートが反応性に優れるため特に好ましい。
(A)成分の製造方法におけるエステル交換反応触媒としては、前記した通り、(A)成分中の高分子量体が少ないために低粘度で不純物が少なく、このため前記物性に優れる多官能(メタ)アクリレート混合物を製造できるとの理由で、触媒として下記触媒X及びYを併用する。
触媒X:アザビシクロ構造を有する環状3級アミン又はその塩若しくは錯体(以下、「アザビシクロ系化合物」という)、アミジン又はその塩若しくは錯体(以下、「アミジン系化合物」という)、並びにピリジン環を有する化合物又はその塩若しくは錯体(以下、「ピリジン系化合物」という)からなる群から選ばれる一種以上の化合物。
触媒Y:亜鉛を含む化合物。
以下、触媒X及び触媒Yについて説明する。
(A)成分の製造方法における触媒Xは、アザビシクロ系化合物、アミジン系化合物及びピリジン系化合物からなる群から選ばれる一種以上の化合物である。
触媒Xとして使用するこれら化合物は、触媒活性に優れ(A)成分を好ましく製造できる他、反応終了後に後記する触媒Yと錯体を形成し、当該錯体は吸着等による簡便な方法により反応終了後の反応液から容易に除去できる。特に、アザシクロ系化合物は、その触媒Yとの錯体が反応液に難溶解性となるため、ろ過及び吸着等によりさらに容易に除去することができる。
一方、ホスフィン系化合物は、触媒活性に優れるものの、触媒Yと錯体を形成し難いか、又は、錯体を形成した場合は反応液に易溶解性であり、反応終了後の反応液中にホスフィン系化合物又は錯体の大部分が溶解したままとなるため、ろ過及び吸着等による簡便な方法により反応液から除去し難い。このため、最終製品中にもホスフィン系触媒が残存してしまい、これにより製品の保存中に、濁りや触媒の析出が発生したり、経時的に増粘又はゲル化してしまうという保存安定性の問題を生じるものであり、組成物の成分として使用する場合も同様の問題を有するものであった。
触媒Yは、亜鉛を含む化合物である。
触媒Yとしては、亜鉛を含む化合物であれば種々の化合物を使用することができるが、反応性に優れることから有機酸亜鉛及び亜鉛ジケトンエノラートが好ましい。
有機酸亜鉛としては、蓚酸亜鉛等の二塩基酸亜鉛及び下記一般式(3)で表される化合物を挙げることができる。
前記式(3)の化合物としては、R6及びR7が、炭素数1~20の直鎖状又は分岐状アルキル基である化合物が好ましい。R6及びR7において、炭素数1~20の直鎖状又は分岐状アルキル基は、フッ素及び塩素等のハロゲン原子を有しない官能基であり、当該官能基を有する触媒Yは、高収率で多官能(メタ)アクリレートを製造できるため好ましい。
尚、これらの亜鉛を含む化合物について、その水和物又は溶媒和物又は触媒Xとの錯体が存在する場合には、該水和物及び溶媒和物及び触媒Xとの錯体も(A)成分の製造方法における触媒Yとして使用できる。
例えば、金属亜鉛、酸化亜鉛、水酸化亜鉛、塩化亜鉛及び硝酸亜鉛等の亜鉛化合物(以下、「原料亜鉛化合物」という)を原料として使用し、有機酸亜鉛の場合は、原料亜鉛化合物と有機酸を反応させる方法、亜鉛ジケトンエノラートの場合は、原料亜鉛化合物と1,3-ジケトンを反応させる方法等が挙げられる。
(A)成分は、前記触媒X及びYの存在下に、多価アルコールと単官能(メタ)アクリレートをエステル交換反応させて製造される。
(A)成分の製造方法における触媒Xと触媒Yの使用割合は特に制限はないが、触媒Yの1モルに対して、触媒Xを0.005~10.0モル使用することが好ましく、より好ましくは0.05~5.0モルである。0.005モル以上使用することで、目的の多官能(メタ)アクリレートの生成量を多くすることができ、10.0モル以下とすることで、副生成物の生成や反応液の着色を抑制し、反応終了後の精製工程を簡便にすることができる。
この組合せが、多官能(メタ)アクリレートを収率よく得られることに加え、反応終了後の色調に優れることから、色調が重要視される各種工業用途に好適に使用できる。さらには比較的安価に入手可能な触媒であることから、経済的に有利な製造方法となる。
溶媒の具体例としては、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、n-オクタン、n-ノナン、n-デカン、ベンゼン、トルエン、キシレン、エチルベンゼン、ジエチルベンゼン、イソプロピルベンゼン、アミルベンゼン、ジアミルベンゼン、トリアミルベンゼン、ドデシルベンゼン、ジドデシルベンゼン、アミルトルエン、イソプロピルトルエン、デカリン及びテトラリン等の炭化水素類;ジエチルエーテル、ジプロピルエーテル、ジイソプロピルエーテル、ジブチルエーテル、ジアミルエーテル、ジエチルアセタール、ジヘキシルアセタール、t-ブチルメチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、テトラヒドロピラン、トリオキサン、ジオキサン、アニソール、ジフェニルエーテル、ジメチルセロソルブ、ジグライム、トリグライム及びテトラグライム等のエーテル類;18-クラウン-6等のクラウンエーテル類;安息香酸メチル及びγ-ブチロラクトン等のエステル類;アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン、アセトフェノン及びベンゾフェノン等のケトン類;炭酸ジメチル、炭酸ジエチル、エチレンカーボネート、プロピレンカーボネート、1,2-ブチレンカーボネートなどのカーボネート化合物;スルホラン等のスルホン類;ジメチルスルホキサイド等のスルホキサイド類;尿素類又はその誘導体;トリブチルホスフィンオキサイド等のホスフィンオキサイド類、イミダゾリウム塩、ピペリジニウム塩及びピリジニウム塩等のイオン液体;シリコンオイル並びに;水等が挙げられる。
これらの溶媒の中では、炭化水素類、エーテル類、カーボネート化合物及びイオン液体が好ましい。
これらの溶媒は単独で使用してもよく、二種以上を任意に組み合わせて混合溶媒として使用してもよい。
重合禁止剤の具体例としては、ハイドロキノン、tert-ブチルハイドロキノン、ハイドロキノンモノメチルエーテル、2,6-ジ-tert-ブチル-4-メチルフェノール、2,4,6-トリ-tert-ブチルフェノール、4-tert-ブチルカテコール、ベンゾキノン、フェノチアジン、N-ニトロソ-N-フェニルヒドロキシルアミンアンモニウム、2,2,6,6-テトラメチルピペリジン-1-オキシル、4-ヒドロキシ-2,2,6,6-テトラメチルピペリジン-1-オキシル等の有機系重合禁止剤、塩化銅、硫酸銅及び硫酸鉄等の無機系重合禁止剤、並びにジブチルジチオカルバミン酸銅、N-ニトロソ-N-フェニルヒドロキシルアミンアルミニウム塩等の有機塩系重合禁止剤が挙げられる。
重合禁止剤は、一種を単独で添加しても又は二種以上を任意に組み合わせて添加してもよく、本発明の最初から添加してもよいし、途中から添加してもよい。又、所望の使用量を一括で添加してもよいし、分割して添加してもよい。又、精留塔を経由して連続的に添加してもよい。
重合禁止剤の添加割合としては、反応液中に5~30,000wtppmが好ましく、より好ましくは25~10,000wtppmである。この割合を5wtppm以上とすることで、重合禁止効果を発揮することができ、30,000wtppm以下にすることで、反応液の着色を抑制でき、反応終了後の精製工程を簡便にすることができ、又、得られる(A)成分の硬化速度の低下を防止することができる。
分離・精製操作としては、晶析操作、ろ過操作、蒸留操作及び抽出操作等が挙げられ、これらを組合わせることが好ましい。晶析操作としては、冷却晶析及び濃縮晶析等が挙げられ、ろ過操作としては、加圧ろ過、吸引ろ過及び遠心ろ過等が挙げられ、蒸留操作としては、単式蒸留、分別蒸留、分子蒸留及び水蒸気蒸留等が挙げられ、抽出操作としては、固液抽出、液液抽出等が挙げられる。
該分離精製操作においては溶媒を使用してもよい。又、本発明で使用した触媒及び/又は重合禁止剤を中和するための中和剤や、吸着除去するための吸着剤、副生成物を分解又は除去するための酸及び/又はアルカリ、色調を改善するための活性炭、ろ過効率及びろ過速度を向上するためのケイソウ土等を使用してもよい。
(A)成分は、多価アルコール(ジグリセリン又は/及びグリセリン)と単官能(メタ)アクリレートのエステル交換反応で得られる多官能(メタ)アクリレートの混合物であり、水酸基を有しない多官能(メタ)アクリレートと水酸基を有する多官能(メタ)アクリレートの混合物である。
例えば、ジグリセリンの場合、ジグリセリンジ(メタ)アクリレート、ジグリセリントリ(メタ)アクリレート及びジグリセリンテトラ(メタ)アクリレートの混合物である。この場合、ジグリセリントリ(メタ)アクリレート及びジグリセリンテトラ(メタ)アクリレートを主成分とする(メタ)アクリレート混合物が好ましい。
又、グリセリンの場合、グリセリンジ(メタ)アクリレート及びグリセリントリ(メタ)アクリレートの混合物である。この場合、グリセリントリ(メタ)アクリレートを主成分とする(メタ)アクリレート混合物が好ましい。
多官能(メタ)アクリレートの混合物中には、モノ(メタ)アクリレートを少量含んでいても良い。
(A)成分をコーティング剤、インキ及びパターン形成等の好ましい用途に使用する場合の水酸基価としては、水酸基価が低いものが好ましい。具体的には、水酸基価が60mgKOH/g以下のものが好ましく、より好ましくは45mgKOH/g以下である。
(A)成分の水酸基価をこの範囲とすることで、組成物を低粘度にすることができ、硬化物の硬度に優れた組成物を得ることができる。
尚、本発明において水酸基価とは、試料1g中の水酸基と当量の水酸化カリウムのmg数を意味する。
(A)成分中の高分子量体としては、ゲルパーミエーションクロマトグラフィー(以下、「GPC」という)測定により得られた値であって、下記式(1)で定義される高分子量体の面積%として30%未満であることが好ましい。
高分子量体の面積%=〔(R-I-L)/R〕×100 ・・・(1)
式(1)における記号及び用語は、以下を意味する。
・R:(A)成分中の検出ピークの総面積
・I:理想構造(メタ)アクリレートを含む検出ピークの面積
・L:理想構造(メタ)アクリレートを含む検出ピークよりも重量平均分子量(以下、「Mw」という)が小さい検出ピークの総面積
・理想構造(メタ)アクリレート:原料アルコール1分子あたりに含まれる水酸基の数と、同数の(メタ)アクリロイル基を1分子あたりに含み、かつマイケル付加型の構造を有しない多官能(メタ)アクリレートを意味する。
即ち、ジグリセリンを原料とする場合は、ジグリセリンテトラ(メタ)アクリレートを意味し、グリセリンを原料とする場合は、グリセリントリ(メタ)アクリレートを意味する。
尚、本発明において、Mwとは、溶媒としてテトラヒドロフラン(以下、「THF」という)を使用し、GPCにより測定した分子量をポリスチレンの分子量を基準にして換算した値を意味する。
尚、本発明におけるGPCにより測定した分子量は、以下の条件で測定した値を意味する。
・検出器:示差屈折計(RI検出器)
・カラムの種類:架橋ポリスチレン系カラム
・カラムの温度:25~50℃の範囲内
・溶離液:THF
本発明は、前記(A)成分を含む硬化型組成物に関する。
組成物の製造方法としては、前記触媒X及びYの存在下に、多価アルコールと単官能(メタ)アクレートをエステル交換反応させ多官能(メタ)アクリレートの混合物を製造する工程を含む製造方法が好ましい。
当該製造方法によれば、(A)成分を高収率で製造でき、しかも得られる(A)成分中の高分子量体が少ないために低粘度で不純物が少なく、このため得られる組成物を各種物性に優れるものとすることができる点で好ましい。
当該工程としては、前記した(A)成分の製造方法に従えば良い。
(A)成分をコーティング剤、インキ及びパターン形成等の好ましい用途に使用する場合には、目的に応じて適宜設定すれば良く、1~100,000mPa・sが好ましく、より好ましくは5~50,000mPa・sである。当該粘度範囲とすることで、組成物の塗工時のレベリング性に優れ、硬化物の外観に優れるものとすることができる。
尚、本発明における粘度とは、E型粘度計を使用して25℃で測定した値を意味する。
本発明の組成物は、前記(A)を必須成分とするものであるが、目的に応じて種々の成分を配合することができる。
その他成分としては、具体的には、光重合開始剤〔以下、「(B)成分」という〕、熱重合開始剤〔以下、「(C)成分」という〕、前記(A)成分以外のエチレン性不飽和基を有する化合物〔以下、「(D)成分」という〕及び有機溶剤〔以下、「(E)成分」という〕等が挙げられる。
以下、これらの成分について説明する。
尚、後記するその他の成分は、例示した化合物の1種のみを使用しても良く、2種以上を併用しても良い。
本発明の組成物を活性エネルギー線硬化型組成物として使用し、さらに電子線硬化型組成物として使用する場合は、(B)成分(光重合開始剤)を含有させず、電子線により硬化させることも可能である。
本発明の組成物を活性エネルギー線硬化型組成物として使用する場合において、特に、活性エネルギー線として紫外線及び可視光線を用いたときには、硬化の容易性やコストの観点から、(B)成分を更に含有することが好ましい。
活性エネルギー線として電子線を使用する場合には、必ずしも配合する必要はないが、硬化性を改善させるため必要に応じて少量配合することもできる。
ベンゾフェノン、2-メチルベンゾフェノン、3-メチルベンゾフェノン、4-メチルベンゾフェノン、2,4,6-トリメチルベンゾフェノン、4-フェニルベンゾフェノン、4-(メチルフェニルチオ)フェニルフェニルメタン、メチル-2-ベンゾフェノン、1-[4-(4-ベンゾイルフェニルスルファニル)フェニル]-2-メチル-2-(4-メチルフェニルスルフォニル)プロパン-1-オン、4,4’-ビス(ジメチルアミノ)ベンゾフェノン、4,4’-ビス(ジエチルアミノ)ベンゾフェノン及び4-メトキシ-4′-ジメチルアミノベンゾフェノン等のベンゾフェノン系化合物;
ビス(2,4,6-トリメチルベンゾイル)フェニルホスフィンオキサイド、2,4,6-トリメチルベンゾイルジフェニルフォスフィンオキサイド、エチル(2,4,6-トリメチルベンゾイル)フェニルフォスフィネート及びビス(2,6-ジメトキシベンゾイル)-2,4,4-トリメチルペンチルフォスフィンオキサイド等のアシルホスフィンオキサイド化合物;
チオキサントン、2-クロロチオキサントン、2,4-ジエチルチオキサントン、イソプロピルチオキサントン、1-クロロ-4-プロピルチオキサントン、3-[3,4-ジメチル-9-オキソ-9H-チオキサントン-2-イル-オキシ]-2-ヒドロキシプロピル-N,N,N―トリメチルアンモニウムクロライド及びフルオロチオキサントン等のチオキサントン系化合物等が挙げられる。
又、硬化膜の膜厚を厚くする必要がある場合、例えば50μm以上とする必要がある場合は、硬化膜内部の硬化性を向上させる目的や、紫外線吸収剤や顔料を併用する場合は、ビス(2,4,6-トリメチルベンゾイル)-フェニルホスフィンオキサイド、2,4,6-トリメチルベンゾイルジフェニルフォスフィンオキサイド、エチル-(2,4,6-トリメチルベンゾイル)フェニルフォスフィネート及びビス(2,6-ジメトキシベンゾイル)-2,4,4-トリメチルペンチルフォスフィンオキサイド等のアシルホスフィンオキサイド化合物や、2-メチル-1-[4-(メチルチオ)]フェニル]-2-モルフォリノプロパン-1-オン、2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)ブタンー1-オン、2-ジメチルアミノ-2-(4-メチルベンジル)-1-(4-モルフォリン-4-イル-フェニル)-ブタン-1-オン等を併用することが好ましい。
尚、本発明において「硬化性成分」とは、熱又は活性エネルギー線により硬化する成分であり、(A)成分を意味し、後記する(D)成分を配合する場合は、(A)及び(D)成分を意味する。
本発明の組成物を熱硬化型組成物として使用する場合には、熱重合開始剤を配合することができる。
熱重合開始剤としては、種々の化合物を使用することができ、有機過酸化物及びアゾ系開始剤が好ましい。
有機過酸化物の具体例としては、1,1-ビス(t-ブチルパーオキシ)2-メチルシクロヘキサン、1,1-ビス(t-ヘキシルパーオキシ)-3,3,5-トリメチルシクロヘキサン、1,1-ビス(t-ヘキシルパーオキシ)シクロヘキサン、1,1-ビス(t-ブチルパーオキシ)-3,3,5-トリメチルシクロヘキサン、1,1-ビス(t-ブチルパーオキシ)シクロヘキサン、2,2-ビス(4,4-ジ-ブチルパーオキシシクロヘキシル)プロパン、1,1-ビス(t-ブチルパーオキシ)シクロドデカン、t-ヘキシルパーオキシイソプロピルモノカーボネート、t-ブチルパーオキシマレイン酸、t-ブチルパーオキシ-3,5,5-トリメチルヘキサノエート、t-ブチルパーオキシラウレート、2,5-ジメチル-2,5-ジ(m-トルオイルパーオキシ)ヘキサン、t-ブチルパーオキシイソプロピルモノカーボネート、t-ブチルパーオキシ2-エチルヘキシルモノカーボネート、t-ヘキシルパーオキシベンゾエート、2,5-ジーメチル-2,5-ジ(ベンゾイルパーオキシ)ヘキサン、t-ブチルパーオキシアセテート、2,2-ビス(t-ブチルパーオキシ)ブタン、t-ブチルパーオキシベンゾエート、n-ブチル-4,4-ビス(t-ブチルパーオキシ)バレレート、ジ-t-ブチルパーオキシイソフタレート、α、α‘-ビス(t-ブチルパーオキシ)ジイソプロピルベンゼン、ジクミルパーオキサイド、2,5-ジメチル-2,5-ジ(t-ブチルパーオキシ)ヘキサン、t-ブチルクミルパーオキサイド、ジ-t-ブチルパーオキサイド、p-メンタンハイドロパーオキサイド、2,5-ジメチル-2,5-ジ(t-ブチルパーオキシ)ヘキシン-3、ジイソプロピルベンゼンハイドロパーオキサイド、t-ブチルトリメチルシリルパーオキサイド、1,1,3,3-テトラメチルブチルハイドロパーオキサイド、クメンハイドロパーオキサイド、t-ヘキシルハイドロパーオキサイド、t-ブチルハイドロパーオキサイド等が挙げられる。
アゾ系化合物の具体例としては、1,1’-アゾビス(シクロヘキサン-1-カルボニトリル)、2-(カルバモイルアゾ)イソブチロニトリル、2-フェニルアゾ-4-メトキシ-2,4-ジメチルバレロニトリル、アゾジ-t-オクタン、アゾジ-t-ブタン等が挙げられる。
これらは単独で用いても良いし、2種以上を併用しても良い。又、有機過酸化物は還元剤と組み合わせることによりレドックス反応とすることも可能である。
熱重合開始剤を単独で用いる場合は、通常のラジカル熱重合の常套手段にしたがって行えばよく、場合によっては(B)成分(光重合開始剤)と併用し、光硬化させた後にさらに反応率を向上させる目的で熱硬化を行うこともできる。
(D)成分は、前記(A)成分以外のエチレン性不飽和化合物であり、組成物の硬化物に種々の物性を付与する目的で配合する。
(D)成分におけるエチレン性不飽和基としては、(メタ)アクリロイル基、(メタ)アクリルアミド基、ビニル基及び(メタ)アリル基等が挙げられ、(メタ)アクリロイル基が好ましい。
尚、下記において、「単官能」とは、エチレン性不飽和基を1個有する化合物を意味し、「○官能」とはエチレン性不飽和基を○個有する化合物を意味し、「多官能」とはエチレン性不飽和基を2個以上有する化合物を意味する。
前記した単官能(メタ)アクリレート以外の化合物としては、(メタ)アクリル酸、アクリル酸のマイケル付加型のダイマー、ω-カルボキシ-ポリカプロラクトンモノ(メタ)アクリレート、フタル酸モノヒドロキシエチル(メタ)アクリレート、エチルカルビトール(メタ)アクリレート、ブチルカルビトール(メタ)アクリレート、2-エチルヘキシルカルビトール(メタ)アクリレート、ベンジル(メタ)アクリレート、フェニル(メタ)アクリレート、フェノールのアルキレンオキサイド付加物の(メタ)アクリレート、アルキルフェノールのアルキレンオキサイド付加物の(メタ)アクリレート、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、4-ヒドロキシブチルアクリレート、パラクミルフェノールのアルキレンオキサイド付加物の(メタ)アクリレート、オルトフェニルフェノール(メタ)アクリレート、オルトフェニルフェノールのアルキレンオキサイド付加物の(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、イソボルニル(メタ)アクリレート、トリシクロデカンメチロール(メタ)アクリレート、2-ヒドロキシ-3-フェノキシプロピル(メタ)アクリレート、N-(2-(メタ)アクリロキシエチル)ヘキサヒドロフタルイミド、N-(2-(メタ)アクリロキシエチル)テトラヒドロフタルイミド、N,N-ジメチルアクリルアミド、アクリロイルモルホリン、N-ビニルピロリドン及びN-ビニルカプロラクタム等が挙げられる。
ペンタエリスリトールアルキレンオキサイド付加物のトリ又はテトラ(メタ)アクリレート、ジトリメチロールプロパンアルキレンオキサイド付加物のトリ又はテトラ(メタ)アクリレート、ジペンタエリスリトールアルキレンオキサイド付加物のトリ、テトラ、ペンタ又はヘキサ(メタ)アクリレート等のポリオールアルキレンオキサイド付加物のポリ(メタ)アクリレート;
イソシアヌル酸アルキレンオキサイド付加物のトリ(メタ)アクリレート;並びに
ペンタエリスリトールトリ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート等の水酸基を有し3個以上の(メタ)アクリロイル基を有する化合物と有機ポリイソシアネートとの反応物であるウレタン(メタ)アクリレート等
を挙げることができる。
前記における、アルキレンオキサイド付加物の例としては、エチレンオキサイド付加物、プロピレンオキサイド付加物、並びに、エチレンオキサイド及びプロピレンオキサイド付加物等が挙げられる。
又、前記有機ポリイソシアネートとしては、ヘキサメチレンジイソシアネート、テトラメチレンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、リジンジイソシアネート、イソホロンジイソシアネート、ノルボルナンジイソシアネート、水素化トリレンジイソシアネート、水素化4,4’-ジフェニルメタンジイソシアネート、水素化キシリレンジイソシアネート、4,4’-ジシクロヘキシルメタンジイソシアネート、ヘキサメチレンジイソシアネートの三量体等を挙げることができる。
(D)成分の含有割合が60重量%以下とすることで、特に(D)成分が多官能エチレン性不飽和化合物の場合には、硬化膜が脆くなることを防止することができる。
本発明の組成物は、基材への塗工性を改善する等の目的で、(E)成分の有機溶剤を含むことができる。
これらの中でも、アルキレングリコールモノエーテル化合物、ケトン化合物が好ましく、アルキレングリコールモノエーテル化合物がより好ましい。
本発明の組成物は、種々の用途に使用可能である。
好ましい用途の例としては、ハードコート等のコーティング用組成物、金型転写やナノインプリント等で使用する成形材用組成物、オフセットやインクジェット印刷等のインキ用組成物、感光性平版印刷版やカラーレジスト等のパターン形成用組成物等が挙げられる。
以下、各組成物について説明する。
本発明の組成物は、薄膜硬化性が優れ、硬化物の硬度が高いため、コーティング用組成物として好ましく使用することができ、(A)成分は低粘度であるため無溶剤型のコーティング用組成物としてより好ましく使用することができる。
その他成分としては、具体的には、前記した(B)、(C)、(D)及び(E)成分の他、酸化防止剤、紫外線吸収剤、顔料・染料、シランカップリング剤、表面改質剤、ポリマー及び重合禁止剤等が挙げられる。
以下、これらの成分について説明する。
尚、後記するその他の成分は、例示した化合物の1種のみを使用しても良く、2種以上を併用しても良い。
酸化防止剤は、硬化膜の耐熱性、耐候性等の耐久性を向上させる目的で配合する。
酸化防止剤としては、たとえばフェノール系酸化防止剤やリン系酸化防止剤、硫黄系酸化防止剤等が挙げられる。
フェノール系酸化防止剤としては、たとえば、ジt-ブチルヒドロキシトルエン等のヒンダードフェノール類を挙げることができる。市販されているものとしては、(株)アデカ製のAO-20、AO-30、AO-40、AO-50、AO-60、AO-70、AO-80等が挙げられる。
リン系酸化防止剤としては、トリアルキルホスフィン、トリアリールホスフィン等のホスフィン類や、亜リン酸トリアルキルや亜リン酸トリアリール等が挙げられる。これらの誘導体で市販品としては、たとえば(株)アデカ製、アデカスタブPEP-4C、PEP-8、PEP-24G、PEP-36、HP-10、260、522A、329K、1178、1500、135A、3010等が挙げられる。
硫黄系酸化防止剤としては、チオエーテル系化合物が挙げられ、市販品としては(株)アデカ製AO-23、AO-412S、AO-503A等が挙げられる。
これらは1種を用いても2種類以上を用いてもよい。これら酸化防止剤の好ましい組合せとしては、フェノール系酸化防止剤とリン系酸化防止剤との併用、及びフェノール系酸化防止剤と硫黄系酸化防止剤の併用が挙げられる。
酸化防止剤の含有割合としては、目的に応じて適宜設定すれば良く、硬化性成分合計量100重量部に対して0.01~5重量部が好ましく、より好ましくは0.1~1重量部である。
含有割合を0.1重量部以上とすることで、組成物の耐久性を向上させることができ、一方、5重量部以下とすることで、硬化性や密着性を良好にすることができる。
紫外線吸収剤は、硬化膜の耐光性を向上させる目的で配合する。
紫外線吸収剤としては、BASF社製TINUVIN400、TINUVIN405、TINUVIN460、TINUVIN479等のトリアジン系紫外線吸収剤や、TINUVIN900、TINUVIN928、TINUVIN1130等のベンゾトリアゾール系紫外線吸収剤を挙げることができる。
紫外線吸収剤の含有割合としては、目的に応じて適宜設定すれば良く、硬化性成分合計量100重量部に対して0.01~5重量部が好ましく、より好ましくは0.1~1重量部である。含有割合を0.01重量%以上とすることで、硬化膜の耐光性を良好なものとすることができ、一方、5重量%以下とすることで、組成物の硬化性に優れるものとすることができる。
顔料としては、有機顔料及び無機顔料等が挙げられる。
有機顔料の具体例としては、トルイジンレッド、トルイジンマルーン、ハンザエロー、ベンジジンエロー及びピラゾロンレッド等の不溶性アゾ顔料;リトールレッド、ヘリオボルドー、ピグメントスカーレット及びパーマネントレッド2B等の溶性アゾ顔料;アリザリン、インダントロン及びチオインジゴマルーン等の建染染料からの誘導体;フタロシアニンブルー及びフタロシアニングリーン等のフタロシアニン系有機顔料;キナクリドンレッド及びキナクリドンマゼンタ等のキナクリドン系有機顔料、ペリレンレッド及びペリレンスカーレット等のペリレン系有機顔料;イソインドリノンエロー及びイソインドリノンオレンジ等のイソインドリノン系有機顔料;ピランスロンレッド及びピランスロンオレンジ等のピランスロン系有機顔料;チオインジゴ系有機顔料;縮合アゾ系有機顔料;ベンズイミダゾロン系有機顔料;キノフタロンエロー等のキノフタロン系有機顔料、イソインドリンエロー等のイソインドリン系有機顔料;並びにその他の顔料として、フラバンスロンエロー、アシルアミドエロー、ニッケルアゾエロー、銅アゾメチンエロー、ペリノンオレンジ、アンスロンオレンジ、ジアンスラキノニルレッド及びジオキサジンバイオレット等が挙げられる。
又、前記無機顔料の具体例としては、酸化チタン、硫酸バリウム、炭酸カルシウム、亜鉛華、硫酸鉛、黄色鉛、亜鉛黄、べんがら(赤色酸化鉄(III))、カドミウム赤、群青、紺青、酸化クロム緑、コバルト緑、アンバー、チタンブラック及び合成鉄黒等を挙げることができる。尚、前記フィラーで例示したカーボンブラックは、無機顔料としても使用することができる。
染料としては、従来から知られた種々の化合物を使用することができる。
シランカップリング剤は、硬化膜と基材との界面接着強度を改善する目的で配合する。
シランカップリング剤としては、基材との接着性向上に寄与できるものであれば特に特に限定されるものではない。
配合割合を0.1重量部以上にすることで、組成物の接着力を向上させることができ、一方、10重量部以下とすることで、接着力の経時変化を防止することができる。
本発明の組成物は、塗布時のレベリング性を高める目的や、硬化膜の滑り性を高めて耐擦傷性を高める目的等のため、表面改質剤を添加してもよい。
表面改質剤としては、表面調整剤、界面活性剤、レベリング剤、消泡剤、スベリ性付与剤及び防汚性付与剤等が挙げられ、これら公知の表面改質剤を使用することができる。
それらのうち、シリコーン系表面改質剤及びフッ素系表面改質剤が好適に挙げられる。具体例としては、シリコーン鎖とポリアルキレンオキサイド鎖とを有するシリコーン系ポリマー及びオリゴマー、シリコーン鎖とポリエステル鎖とを有するシリコーン系ポリマー及びオリゴマー、パーフルオロアルキル基とポリアルキレンオキサイド鎖とを有するフッ素系ポリマー及びオリゴマー、並びに、パーフルオロアルキルエーテル鎖とポリアルキレンオキサイド鎖とを有するフッ素系ポリマー及びオリゴマー等が挙げられる。
又、滑り性の持続力を高める等の目的で、分子中にエチレン性不飽和基、好ましくは(メタ)アクリロイル基を有する表面改質剤を使用してもよい。
本発明の組成物は、得られる硬化膜の耐カール性をより改良する目的等で、ポリマーをさらに含有していてもよい。
好適なポリマーとしては、(メタ)アクリル系ポリマーが挙げられ、好適な構成モノマーとしては、メチル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、(メタ)アクリル酸、グリシジル(メタ)アクリレート、N-(2-(メタ)アクリロキシエチル)テトラヒドロフタルイミド等が挙げられる。(メタ)アクリル酸を共重合したポリマーの場合、グリシジル(メタ)アクリレートを付加させて(メタ)アクリロイル基をポリマー鎖に導入してもよい。
ポリマーの含有割合は、硬化性成分の合計量100重量部に対して、0.01~10重量部であることが好ましい。上記範囲であると、得られる硬化膜の耐カール性により優れる。
本発明の組成物は、低粘度で、硬化物の硬度が高いため、成形材用組成物として好ましく使用することができる。尚、本発明では、ナノインプリント等の微細加工用途も、便宜上成形材と称する。
その他成分としては、具体的には、前記した(B)、(C)、(D)及び(E)成分の他、酸化防止剤、紫外線吸収剤、顔料・染料、シランカップリング剤、表面改質剤、ポリマー及び重合禁止剤等が挙げられる。
本発明の組成物は、薄膜硬化性に優れるため、単色又は多色印刷後さらに印刷機で印刷される透明なオーバープリントニスインキや黄、紅、藍、墨等のカラー印刷用インキ用として好ましく使用することができる。
インキ用組成物の製造方法としては、従来のインキ用組成物の製造方法に従えば良く、(A)成分、(B)成分(活性エネルギー線が紫外線の場合)、(F)成分、(G)成分、重合禁止剤及びワックスその他添加剤等を配合した後、顔料を加えて、三本ロールミル、ビーズミル等の分散機で分散する方法等が挙げられる。
以下、これらの成分について説明する。
尚、その他の成分は、例示した化合物の1種のみを使用しても良く、2種以上を併用しても良い。
本発明における(F)成分としては、重合性基を有さない例えばジアリルフタレート樹脂等、1分子中に少なくとも1つ以上の重合性基を有するエポキシアクリレート合物、ウレタンアクリレート、ポリエステルアクリレート等が挙げられる。
(G)成分の顔料としては、有機顔料及び無機顔料等が挙げられる。
有機顔料としては、公知公用の着色用有機顔料を挙げることができ、例えば「有機顔料ハンドブック(著者:橋本勲、発行所:カラーオフィス、2006年初版)」に掲載される印刷インキ用有機顔料等が挙げられ、溶性アゾ顔料、不溶性アゾ顔料、縮合アゾ顔料、金属フタロシアニン顔料、無金属フタロシアニン顔料、キナクリドン顔料、ペリレン顔料、ペリノン顔料、イソインドリノン顔料、イソインドリン顔料、ジオキサジン顔料、チオインジゴ顔料、アンスラキノン系顔料、キノフタロン顔料、金属錯体顔料、ジケトピロロピロール顔料、カーボンブラック顔料、その他多環式顔料等が使用可能である。
これら無機微粒子は、インキ中に0.1~20重量%の範囲で使用することにより、インキの流動性調整、ミスチング防止、紙等の印刷基材への浸透防止といった効果を得ることが可能である。
可塑剤及び耐摩擦剤として、パラフィンワックス、カルナバワックス、みつろう、マイクロクリスタリンワックス、ポリエチレンワックス、酸化ポリエチレンワックス、ポリテトラフルオロエチレンワックス、アマイドワックス等のワックスコンパウンド、ヤシ油脂肪酸や大豆油脂肪酸等のC8~C18程度の範囲にある脂肪酸等を本発明の目的を妨げない範囲において配合して使用することができる。
本発明の組成物は、露光感度が高く現像性に非常に優れ、精密で正確なパターンを形成することができるため、パターン形成用組成物として好ましく使用することができる。
その他成分としては、具体的には、前記した(B)、(D)、(E)成分、酸化防止剤、紫外線吸収剤、シランカップリング剤、表面改質剤及び重合禁止剤の他、アルカリ可溶性樹脂〔以下「(H)成分」という〕等が挙げられる。
以下、(H)成分について説明する。
尚、その他の成分は、例示した化合物の1種のみを使用しても良く、2種以上を併用しても良い。
本発明における(H)成分としては、(A)成分に対してバインダーとして作用し、現像処理工程において用いられる現像液、特に好ましくはアルカリ現像液に対して可溶性を有するものであれば、特に限定されるものではない。
(H)成分としては、付加重合体、ポリエステル、エポキシ樹脂及びポリエーテル等が挙げられ、エチレン性不飽和単量体を重合体して得られる付加重合体が好ましい。
(H)成分としては、カルボキシル基を有するアルカリ可溶性樹脂が好ましく、特に、1個以上のカルボキシル基を有するエチレン性不飽和単量体(以下「カルボキシル基含有不飽和単量体」という)とこれと共重合可能なエチレン性不飽和単量体(以下「共重合性不飽和単量体」という)との共重合体(以下「カルボキシル基含有共重合体」という)が好ましい。
カルボキシル基含有不飽和単量体は、単独で又は2種以上を混合して使用することができる。
これらの共重合性不飽和単量体は、単独で又は2種以上を混合して使用することができる。
エチレン性不飽和基を側鎖に有するアルカリ可溶性樹脂としては、カルボキシル基を有するアルカリ可溶性樹脂が好ましい。当該樹脂としては、前記したカルボキシル基含有共重合体に、エポキシ基を有する不飽和化合物(以下「エポキシ系不飽和化合物」という)を付加したもの等が挙げられる。
エポキシ系不飽和化合物としては、グリシジル(メタ)アクリレート及びシクロヘキセンオキサイド含有(メタ)アクリレート等のエポキシ基含有(メタ)アクリレート等が挙げられる。
付加反応の方法としては、常法に従えば良く、有機溶媒中又は無溶剤で、カルボキシル基含有共重合体にエポキシ系不飽和化合物を付加することにより製造することができる。付加反応の条件としては、各反応に応じて反応温度、反応時間及び触媒を適宜選択すれば良い。
尚、本発明においてMw及びMnは、GPC(溶出溶媒:テトラヒドロフラン)で測定した分子量をポリスチレン換算した値を意味する。
本発明においては、このような特定のMw及びMnを有する(H)成分を使用することによって、現像性に優れた感光性樹脂組成物が得られ、それにより、シャープなパターンエッジを有するパターンを形成することができるとともに、現像時に未露光部の基板上及び遮光層上に残渣、地汚れ、膜残り等が発生し難くなる。又、(H)成分のMwとMnの比(Mw/Mn)は、通常、1~5、好ましくは1~4である。
(H)成分は、単独で又は2種以上を併用して使用することができる。
(A)成分と(H)成分の組成物中の割合としては、(A)成分と(H)成分の合計量として組成物中に10~50重量%が好ましい。この割合が10重量%以上とすることで、プリベーク後の膜厚が薄くなることを防止でき、一方50重量%以下とすることで、組成物の粘度を適切となり塗工性が不良になることを防止でき、プリベーク後の膜厚が厚くなることを防止できる。
4-1.コーティング用組成物の使用方法
本発明の組成物の使用方法としては、常法に従えば良い。
例えば、基材に組成物を塗布した後、活性エネルギー線を照射するか又は加熱することにより硬化させて硬化させる方法等が挙げられる。
具体的には、適用される基材に組成物を通常の塗装方法により塗布した後、活性エネルギー線硬化型組成物の場合には活性エネルギー線を照射して硬化させる方法、又熱硬化型組成物の場合は加熱して硬化させる方法等が挙げられる。
活性エネルギー線の照射方法や加熱方法は、従来の硬化方法として知られている一般的
な方法を採用すれば良い。
又、組成物に(C)成分(光重合開始剤)及び(D)成分(熱重合開始剤)を併用し、これを活性エネルギー線照射した後、加熱硬化させることにより、基材との密着性を向上させる方法も採用することができる。
プラスチックの具体例としては、ポリビニルアルコール、トリアセチルセルロース及びジアセチルセルロース等のセルロースアセテート樹脂、アクリル樹脂、ポリエチレンテレフタレート、ポリカーボネート、ポリアリレート、ポリエーテルサルホン、ノルボルネン等の環状オレフィンをモノマーとする環状ポリオレフィン樹脂、ポリ塩化ビニル、エポキシ樹脂及びポリウレタン樹脂等が挙げられる。
木材としては、自然の木材及び合成木材等が挙げられる。
金属としては、鋼板、アルミ及びクロム等の金属、酸化亜鉛(ZnO)及び酸化インジウムスズ(ITO)等の金属酸化物等が挙げられる。
無機材料としては、ガラス、モルタル、コンクリート及び石材等が挙げられる。
これらの中でも、プラスチック基材が特に好ましい。
紫外線照射装置としては、高圧水銀ランプ、メタルハライドランプ、紫外線(UV)無電極ランプ、発光ダイオード(LED)等が挙げられる。
照射エネルギーは、活性エネルギー線の種類や配合組成に応じて適宜設定すれば良く、一例として高圧水銀ランプを使用する場合を挙げると、UV-A領域の照射エネルギーで10
0~5,000mJ/cm2が好ましく、200~1,000mJ/cm2がより好ましい。
本発明の組成物を成形材用途で使用する場合の使用方法としては、常法に従えば良い。
具体的には、目的の形状を有するスタンパを称される金型に組成物を塗布し、フィルム又はシート基材(以下これらをまとめて「フィルム基材」という。)でラミネートした後に、活性エネルギー線を照射し硬化させる方法、所定の型枠に組成物を注入した後、活性エネルギー線硬化型組成物の場合には活性エネルギー線を照射することにより硬化させる方法、又熱硬化型組成物の場合は加熱して硬化させる方法等が挙げられる。
紫外線照射装置としては、前記と同様の装置が挙げられる。
照射エネルギーとしては、活性エネルギー線の種類や配合組成に応じて適宜設定すれば良く、前記と同様の照射エネルギーが挙げられる。
比較的膜厚の薄いレンズシートを製造する場合は、本発明の組成物を透明基板に塗布した後、目的のレンズの形状を有するスタンパと称される金型を密着させる。
次いで、透明基板側から活性エネルギー線を照射して、組成物を硬化させ、この後、金型から剥離させる。
次いで、透明基板側から活性エネルギー線を照射して組成物を硬化させ、この後金型を脱型させる。
例えば、基材に組成物を塗布した後、微細加工パターンを有し透明性を有する型(モールド)をプレスする。
次いで、透明のモールド上から活性エネルギー線を照射して組成物を硬化させ、この後モールドを脱型させる方法等を使用することができる。
本発明の印刷物で使用する印刷基材としては、特に限定は無く、例えば、上質紙、コート紙、アート紙、模造紙、薄紙、厚紙等の紙、各種合成紙、ポリエステル樹脂、アクリル樹脂、塩化ビニル樹脂、塩化ビニリデン樹脂、ポリビニルアルコール、ポリエチレン、ポリプロピレン、ポリアクリロニトリル、エチレン酢酸ビニル共重合体、エチレンビニルアルコール共重合体、エチレンメタクリル酸共重合体、ナイロン、ポリ乳酸、ポリカーボネート等のフィルム又はシート、セロファン、アルミニウムフォイル、その他従来から印刷基材として使用されている各種基材を挙げることが出来る。
これらの中でも、紙基材が特に好ましい。
紫外線照射装置としては、前記と同様の装置が挙げられる。
照射エネルギーとしては、活性エネルギー線の種類や配合組成に応じて適宜設定すれば良く、前記と同様の照射エネルギーが挙げられる。
パターン形成用組成物としては、感光性平版印刷版、エッチングレジスト及びソルダーレジスト等のレジスト、液晶パネル製造における、柱状スペーサー、カラーフィルターにおける画素やブラックマトリックス等を形成のための着色組成物、及びカラーフィルター保護膜等が挙げられる。
柱状スペーサー及びカラーフィルター保護膜用途で使用する場合には、塗工性、現像性を改良するために、組成物にポリオキシエチレンラウリルエーテル等のノニオン系界面活性剤や、フッ素系界面活性剤を添加することもできる。又、必要に応じて、接着助剤、保存安定剤及び消泡剤等を適宜添加してもよい。
以下、柱状スペーサー(以下単に「スペーサー」という)及び着色組成物の用途について説明する。
スペーサーは、フォトリソグラフィー法により組成物の光硬化塗膜で形成される。該スペーサーは、液晶パネル基板の任意の場所に任意の大きさで形成することができるが、一般的にはカラーフィルターの遮光部であるブラックマトリックス領域や、TFT電極上に形成することが多い。
スペーサーを形成する方法としては、常法に従えば良く、例えば本発明の組成物を、ガラス等の基板上に、セルギャップを構成するのに必要な膜厚に塗布した後、加熱(以下「プリベーク」と略す。)して塗膜を乾燥させ、露光、現像、後加熱(以下「ポストベーク」と略す。)工程を経て形成する方法等が挙げられる。
塗布方法としては、例えば、印刷法、スプレー法、ロールコート法、バーコート法、カーテンコート法、スピンコート法、ダイコート法(スリットコート法)等が挙げられ、一般的にはスピンコート法やダイコート法を使用する。
使用する光は紫外線や可視光線が好ましく、高圧水銀灯やメタルハライドランプ等から得られる240nm~410nmの波長光を使用する。
光照射条件は、光源の種類や、使用する光重合開始剤の吸収波長、あるいは塗膜の膜厚等によるが、概ね光照射量が50~600mJ/cm2となるようにするのが好ましい。光照射量が50mJ/cm2より小さいと、硬化不良となり現像時に露光部分が脱落しやすく、一方、光照射量が600mJ/cm2よりも大きいと、精細なスペーサーパターンが得られにくい傾向にある。
現像液としては、アルカリ化合物の水溶液が使用できる。アルカリ性化合物としては、例えば、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸水素ナトリウム、ケイ酸ナトリウム、アンモニア、テトラメチルアンモニウムヒドロキシド等が挙げられる。又、現像速度促進のために、現像液に、メタノール、エタノール、イソプロパノール及びベンジルアルコール等の水溶性有機溶剤や、各種界面活性剤を適当量添加してもよい。
現像方法は、液盛り法、ディッピング法及びスプレー法等のいずれでもよい。現像後、パターン部分を0.5~1.5分間水で洗浄し、圧縮空気等で風乾させてスペーサーパターンを得る。
ポストベークすることにより、残留溶剤や現像時に吸収した水分が揮発でき、かつスペーサーの耐熱性が向上できる。スペーサーの膜厚は、液晶パネルのセルギャップ設定値によって異なるが、概ねポストベーク後に3~5μmとなるように設計する。
本発明の組成物を着色組成物として使用する場合には、さらに顔料及び顔料分散剤を配合する。以下、これらの成分について説明する。
有機顔料としては、前記したものの他、より具体的には、カラーインデックス(C.I.;The Society of Dyers and Colourists社発行)においてピグメント(Pigment)に分類されている化合物、すなわち、下記のようなカラーインデックス(C.I.)番号が付されているものを挙げることができる。C.I.ピグメントイエロー1、C.I.ピグメントイエロー3、C.I.ピグメントイエロー12、C.I.ピグメントイエロー13、C.I.ピグメントイエロー83、C.I.ピグメントイエロー138、C.I.ピグメントイエロー139、C.I.ピグメントイエロー150、C.I.ピグメントイエロー180、C.I.ピグメントイエロー185等のイエロー系ピグメント;C.I.ピグメントレッド1、C.I.ピグメントレッド2、C.I.ピグメントレッド3、C.I.ピグメントレッド177、C.I.ピグメントレッド254等のレッド系ピグメント;及び、C.I.ピグメントブルー15、C.I.ピグメントブルー15:3、C.I.ピグメントブルー15:4、C.I.ピグメントブルー15:6等のブルー系ピグメント;C.I.ピグメントグリーン7、C.I.ピグメントグリーン36等のグリーン系ピグメント;C.I.ピグメントバイオレット23、C.I.ピグメントバイオレット23:19等。
又、従来分散困難であった臭素化率の高いフタロシアニン、例えば、モナストラルグリーン6YC、9YC(アビシア株式会社製)の高輝度G顔料、中心金属が銅以外の金属、例えば、Mg、Al、Si、Ti、V、Mn、Fe、Co、Ni、Zn、Ge、Sn等の異種金属フタロシアン顔料からなる高色純度G顔料を用いることができる。
本発明において顔料は、単独で又は2種以上を混合して使用することができる。
使用可能な顔料分散剤として具体例には、ノナノアミド、デカンアミド、ドデカンアミド、N-ドデシルヘキサアミド、N-オクタデシルプロピオアミド、N,N-ジメチルドデカンアミド及びN,N-ジヘキシルアセトアミド等のアミド化合物、ジエチルアミン、ジヘプチルアミン、ジブチルヘキサデシルアミン、N,N,N’,N’-テトラメチルメタンアミン、トリエチルアミン、トリブチルアミン及びトリオクチルアミン等のアミン化合物、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、N,N,N’,N’-(テトラヒドロキシエチル)-1,2-ジアミノエタン、N,N,N’-トリ(ヒドロキシエチル)-1,2-ジアミノエタン、N,N,N’,N’-テトラ(ヒドロキシエチルポリオキシエチレン)-1,2-ジアミノエタン、1,4-ビス(2-ヒドロキシエチル)ピペラジン及び1-(2-ヒドロキシエチル)ピペラジン等のヒドロキシ基を有するアミン等を例示することができ、その他にニペコタミド、イソニペコタミド、ニコチン酸アミド等の化合物を挙げることができる。
尚、以下において「部」とは重量部を意味する。
1)製造例1(エステル交換法によるDGLY-TAの製造)
撹拌機、温度計、ガス導入管、精留塔及び冷却管を取付けた1リットルのフラスコに、ジグリセリンを77.00部(0.46モル)、2-メトキシエチルアクリレートを627.21部(4.82モル)、触媒XとしてDABCOを2.45部(0.02モル)、触媒Yとして酢酸亜鉛を4.00部(0.02モル)、ハイドロキノンモノメチルエーテルを1.42部(仕込んだ原料の総重量に対して2000wtppm)仕込み、含酸素ガス(酸素を5容量%、窒素を95容量%)を液中にバブリングさせた。
反応液温度105~130℃の範囲で加熱撹拌させながら、反応系内の圧力を110~760mmHgの範囲で調整し、エステル交換反応の進行に伴い副生した2-メトキシエタノールと2-メトキシエチルアクリレートの混合液を精留塔及び冷却管を介して反応系から抜出した。又、該抜出液と同重量部の2-メトキシエチルアクリレートを反応系に随時追加した。加熱撹拌開始から27時間後に反応系内の圧力を常圧に戻して抜出を終了した。
反応液を室温まで冷却してノルマルヘキサンを200ml加え、沈殿物をろ過分離した後、ろ液に珪酸アルミニウム〔協和化学工業(株)製キョーワード700(商品名)〕を2.0部、活性炭〔フタムラ化学(株)製太閤S(商品名)〕を0.5部投入し、乾燥空気をバブリングさせながら、温度70~95℃、圧力0.001~100mmHgの範囲で8時間の減圧蒸留を行い、未反応の2-メトキシエチルアクリレートを含む留出液を分離した。釜液に珪藻土〔昭和化学工業(株)製ラヂオライト(商品名)〕を2.0部添加して加圧ろ過を行い、得られたろ液を精製処理物とした。
UV検出器を備えた高速液体クロマトグラフを用いて該精製処理物の組成分析を行った結果、ジグリセリンテトラアクリレートを主要成分として含むことを確認した(以下、「EX-DGLY-TA」という)。精製処理物の収率は93%であった。得られた精製処理物の水酸基価を下記方法に従い測定した結果、6mgKOH/gであった。その結果を表1に示す。
◆水酸基価の測定方法
試料にアセチル化試薬を加えて温浴槽中で加熱処理する。放冷後、フェノールフタレイン溶液を指示薬として水酸化カリウムエタノール溶液で酸を滴定して水酸基価を求める。
多価アルコール及び触媒X及びYとして、下記表1に示す化合物を使用する以外は製造例1と同様の方法に従い、多官能アクリレートを製造した。それらの結果を表1に示す。
多価アルコール及び触媒X及びYとして、下記表2に示す化合物を使用する以外は製造例1と同様の方法に従い、多官能アクリレートを製造した。その結果を表2に示す。
撹拌機、温度計、ガス導入管、精留塔、冷却管及び水分離器を取付けたフラスコに、ジグリセリンを75.77部(0.46モル)、アクリル酸を157.59部(2.19モル)、トルエンを129.50部、70重量%メタンスルホン酸を6.40部、硫酸銅を0.37部(仕込んだ原料の総重量に対して1000wtppm)仕込み、含酸素ガス(酸素を5容量%、窒素を95容量%)を液中にバブリングさせた。反応系内の圧力370mmHgにて加熱還流させながら撹拌して、脱水エステル化反応の進行に伴い副生した水を精留塔及び冷却管を介して反応系から抜出した。この間、反応液の温度は80~90℃の範囲で推移した。加熱撹拌開始から5時間後に反応液の加熱を終了するとともに、反応系内の圧力を常圧に戻して抜出を終了した。
反応液を室温まで冷却した後、トルエンを133部、水を61部加えて撹拌した後静置し、下層(水層)を分離した。その後、上層(有機層)に20%水酸化ナトリウム水溶液を49部加えて撹拌した後静置し、下層(水層)を分離した。その後、上層(有機層)に水を28部加えて撹拌した後静置し、下層(水層)を分離した。上層(有機層)にハイドロキノンモノメチルエーテルを0.018部添加し、乾燥空気をバブリングさせながら、温度60~90℃、圧力0.001~100mmHgの範囲で8時間の減圧蒸留を行い、トルエンを含む留出液を分離した。釜液に珪藻土〔昭和化学工業(株)製ラヂオライト(商品名)〕を2.0部添加して加圧ろ過を行い、得られたろ液を精製処理物とした。
UV検出器を備えた高速液体クロマトグラフを用いて該精製処理物の組成分析を行った結果、ジグリセリンテトラアクリレートを含むことを確認した(以下、「DH-DGLY-TA」という)。精製処理物の収率は11%であった。得られた精製処理物について前記と同様に水酸基価を測定した結果、48mgKOH/gであった。その結果を表3に示す。
多価アルコール及び触媒として、下記表2に示す化合物を使用する以外は比較製造例1と同様に従い、多官能アクリレートを製造した。その結果を表3に示す。
攪拌機、温度計、還流冷却管、滴下ロート及び窒素導入管を備えたセパラブルフラスコに、メタクリル酸メチルを52.9部、ベンジルメタクリレートを22.5部、アクリル酸を24.6部、プロピレングリコールモノメチルエーテルアセテート〔(株)クラレ製「PGM-AC」、以下PGM-ACという〕230部及びジメチル2,2’-アゾビス(2-メチルプロピオネート)を11.0部の割合で投入して均一に溶解させた。その後、窒素気流下で、85℃で4.5時間攪拌し、さらに110℃で1時間反応させた。
(2)上記(1)で得られた溶液に、グリシジルメタクリレートを26.25部、PGM-Acを22.5部、及びハイドロキノンモノメチルエーテルを0.2部の割合で投入した後、100℃で5時間攪拌し、アルカリ可溶性樹脂(h1)を含む反応液B(固形分濃度31.5%)を得た。
このアルカリ可溶性樹脂(h1)の重量平均分子量(Mw)は7,400で、酸価は76mgKOH/g(固形分換算)であった。
1)精製処理物の評価方法
前記製造例及び比較製造例で得られた精製処理物について、下記に示す方法に従い、高分子量体GPC面積%、粘度、耐乳化性、金属イオン濃度及び保存安定性を評価した。それらの結果を表4に示す。
(1)高分子量体GPC面積%
得られた精製処理物について、下記条件のGPC測定により、高分子量体の面積%を算出した。
・装置:Waters(株)製 GPC システム名 1515 2414 717P RI
・検出器:RI検出器
・カラム:ガードカラム 昭和電工(株)製 Shodex KFG(8μm 4.6×10mm)、本カラム2種類 Waters(株)製 styragel HR 4E THF(7.8×300mm)+styragel HR 1THF(7.8×300mm)
・カラムの温度:40℃
・溶離液組成:THF(内部標準として硫黄を0.03%含むもの)、流量0.75mL/分
・高分子量体の面積(%)の算出方法
GPC測定結果より、下記式(1)に基づき算出した。
高分子量体の面積%=〔(R-I-L)/R〕×100 ・・・(1)
式(1)における記号及び用語は、前記した通りである。
得られた精製処理物の粘度をE型粘度計(25℃又は50℃)で測定した。
得られた精製処理物3gをキシレン6gに溶解し、ガラス試験管(18mφ硬質ガラス)に蒸留水9gを入れて栓をした。これを上下に10回振とうし乳化させた後、静置して水層と有機層が完全に分離するまでの時間を測定し、上層及び下層の透明性を下記判定基準により評価した。水分離性と耐乳化性は相関があり、水分離性が良好であるほど、インキに適用した場合の耐乳化性が良好である。
◎:透明。
○:若干濁りあり
△:濁りあり
×:乳濁
JIS K 0121-1993(原子吸光分析通則)に従い、検量線法にて製品中の金属イオン濃度を測定する。試料1gに対し、メタノール9mlを加えフレーム法にて測定する。
多官能アクリレート中の金属イオン濃度と電気特性は相関があり、多官能アクリレート中の金属イオン濃度を低減することで、これを使用したデバイスを形成した際に、金属イオンのマイグレーションを抑制することができる。
得られた精製処理物10gを入れたガラス試験管(18mφ硬質ガラス)を120℃に設定したヒーティングブロックに投入し、6時間加熱した後の外観を、下記判定基準により評価した。
○:増粘又はゲル物が見られない。
×:増粘又はゲル物が見られる。
これに対して、比較製造例1は、触媒Xとしてホスフィン系化合物を使用してエステル交換反応で得られた多官能アクリレートの例であるが、粘度、乳化性、イオン溶出の問題はないものの、保存安定性に問題を有するものであった。
又、比較製造例2及び同3は、従来の脱水エステル法により製造された成分を含み、高分子量体の面積が30%以上含む組成物であるため、粘度が高く、耐乳化性に劣った。又、金属イオン濃度が高く、硬化膜からのイオン溶出による電気特性の低下が懸念されるものであった。
下記表5~7に示す化合物を表5~7に示す割合で撹拌・混合し、活性エネルギー線硬化型組成物を製造した。
得られた組成物を使用し、後記する評価を行った。それらの結果を表5~7に示す。
又、表5~7における略号は下記を意味する。
・IRG907:2-メチル-1-(4-メチルチオフェニル)-2-モルフォリノプロパン-1-オン、BASF社製IRGACURE907
・DAP-A:ジアリルフタレートプレポリマー、ダイソー(株)製ダイソーダップA
・CARMINE 6B:アゾ系赤色顔料 C.I.ピグメントレッド57:1、大同化成工業(株)製カーミン6BNo.6520
(1)硬化性
得られた組成物を、膜厚5μmとなるようポリエチレンテレフタレートフィルム〔東洋紡(株)製、コスモシャインA4300(厚み100μm)〕にバーコーターで塗布した。
得られた試験体を、アイグラフィックス(株)製メタルハライドランプを用い、365nmを中心とする紫外線領域(UV-A)強度800mW/cm2にて、1パスあたり100mJ/cm2の照射エネルギーとなるよう調整したコンベアにて、空気雰囲気下で、搬送を行い、紫外線照射した。
尚、実施例7及び8、比較例7及び8では、塗布膜を100℃のホットプレートで3分間乾燥させ、乾燥膜厚5μmの塗布膜を形成した。
硬化性の評価方法としては、表面のタックがなくなるまでのパス数を求めた。
下記の表5に記載した組成物を、膜厚20μmとなるよう10cm画のガラス基板上にバーコーターで塗布し、アイグラフィックス(株)製高圧水銀ランプを用い、365nmを中心とする紫外線領域(UV-A)強度500mW/cm2にて、1パスあたり800mJ/cm2の照射エネルギーとなるよう調整したコンベアにて、空気雰囲気下で、搬送を行い、紫外線照射した。
った。
得られた硬化膜の硬度を、超微小硬度計〔(株)フィッシャーインストルメンツ製、H-100C〕を用い、室温においてビッカース圧子の最大荷重が20mNとなる条件で表面硬度を測定したときのユニバーサル硬さで評価した。
下記の表6に記載した組成物についても、前記耐乳化性の方法と同様で評価した。
評価結果は、前記表4と同様の結果であった。
10cm角のクロムマスクガラス基板上に、下記の表7に記載した組成物をスピンコーターにより塗布し、この塗布膜を100℃のホットプレートで3分間乾燥させ、乾燥膜厚5μmの塗布膜を形成した。得られた塗膜を液温23℃の0.05%水酸化カリウム水溶液でスプレー現像して、完全に溶解するまでの時間を測定した。
これに対して、従来の脱水エステル法により製造された成分を含む比較例1及び2の組成物は、多官能アクリレートが高分子量体を30面積%以上含む組成物であるため、実施例の組成物よりも硬化膜が硬度に劣った。
又、前記の通り、(A)成分は耐乳化性に優れるためインキ用組成物も耐乳化性に優れ、インキ用組成物として好適なものであった。一方、比較例3及び同4のインキ用組成物は、原料多官能アクリレートの耐乳化性が悪いため、インキ用組成物も耐乳化性が悪く、インキ用途には適さないものであった。
Claims (14)
- 下記触媒X及びYの存在下に、ジグリセリン又は/及びグリセリンと1個の(メタ)アクロイル基を有する化合物をエステル交換反応させて得られる2個以上の(メタ)アクロイル基を有する化合物の混合物(A)を含む硬化型組成物。
触媒X:アザビシクロ構造を有する環状3級アミン又はその塩若しくは錯体、アミジン又はその塩若しくはその錯体、並びにピリジン環を有する化合物又はその塩若しくは錯体からなる群から選ばれる一種以上の化合物。
触媒Y:亜鉛を含む化合物。 - 1個の(メタ)アクリロイル基を有する化合物が、アルコキシアルキル(メタ)アクリレートである請求項1に記載の硬化型組成物。
- 前記触媒Yが、有機酸亜鉛又は/及び亜鉛ジケトンエノラートである請求項1又は請求項2に記載の硬化型組成物。
- 前記(A)成分の水酸基価が60mgKOH/g以下である請求項1~請求項3のいずれか1項に記載の硬化型組成物。
- 前記(A)成分中の高分子量体が、ゲルパーミエーションクロマトグラフィー測定により得られた値であって、下記式(1)で定義される高分子量体の面積%として30%未満である請求項1~請求項4のいずれか1項に記載の硬化型組成物。
高分子量体の面積%=〔(R-I-L)/R〕×100 ・・・(1)
式(1)における記号及び用語は、以下を意味する。
・R:(A)成分の検出ピークの総面積
・I:理想構造(メタ)アクリレートを含む検出ピークの面積
・L:理想構造(メタ)アクリレートを含む検出ピークよりも重量平均分子量が小さい検出ピークの総面積
・理想構造(メタ)アクリレート:原料アルコール1分子あたりに含まれる水酸基の数と、同数の(メタ)アクリロイル基を1分子あたりに含み、かつマイケル付加型の構造を有しない2個以上の(メタ)アクリロイル基を有する化合物を意味する。 - 請求項1~請求項5のいずれか1項に記載の組成物を含む活性エネルギー線硬化型組成物。
- 更に、光重合開始剤(B)を含む請求項6に記載の活性エネルギー線硬化型組成物。
- 請求項6又は請求項7に記載の組成物を含むコーティング用活性エネルギー線硬化型組成物。
- 請求項6又は請求項7に記載の組成物を含むインキ用活性エネルギー線硬化型組成物。
- 請求項6又は請求項7に記載の組成物を含むパターン形成用活性エネルギー線硬化型組成物。
- 下記触媒X及びYの存在下に、ジグリセリン又は/及びグリセリンと1個の(メタ)アクロイル基を有する化合物をエステル交換反応させ2個以上の(メタ)アクロイル基を有する化合物の混合物(A)を製造する工程を含む硬化型組成物の製造方法。
触媒X:アザビシクロ構造を有する環状3級アミン又はその塩若しくは錯体、アミジン又はその塩若しくはその錯体、並びにピリジン環を有する化合物又はその塩若しくは錯体からなる群から選ばれる一種以上の化合物。
触媒Y:亜鉛を含む化合物。 - 1個の(メタ)アクリロイル基を有する化合物がアルコキシアルキル(メタ)アクリレートである請求項11に記載の硬化型組成物の製造方法。
- 前記触媒Yが、有機酸亜鉛又は/及び亜鉛ジケトンエノラートである請求項11又は請求項12に記載の硬化型組成物の製造方法。
- (A)成分を製造した後、光重合開始剤(B)を混合する工程を含む請求項11~請求項13のいずれか1項に記載の硬化型組成物の製造方法。
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CN107709377B (zh) | 2021-04-20 |
JP6583414B2 (ja) | 2019-10-02 |
US10611856B2 (en) | 2020-04-07 |
KR20180022785A (ko) | 2018-03-06 |
JPWO2017002964A1 (ja) | 2018-06-07 |
CN107709377A (zh) | 2018-02-16 |
KR102639863B1 (ko) | 2024-02-22 |
US20180171038A1 (en) | 2018-06-21 |
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