CN104093748A - 光固化性组合物和硬涂剂 - Google Patents
光固化性组合物和硬涂剂 Download PDFInfo
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- CN104093748A CN104093748A CN201380007443.7A CN201380007443A CN104093748A CN 104093748 A CN104093748 A CN 104093748A CN 201380007443 A CN201380007443 A CN 201380007443A CN 104093748 A CN104093748 A CN 104093748A
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- methyl
- group
- photocurable composition
- hard coat
- butyl
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- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 239000006096 absorbing agent Substances 0.000 claims abstract description 27
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 6
- 125000003368 amide group Chemical group 0.000 claims abstract description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 5
- 125000004185 ester group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- -1 (methyl) acryloxy Chemical group 0.000 claims description 115
- 150000001875 compounds Chemical class 0.000 claims description 32
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- 150000003949 imides Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 40
- 125000005462 imide group Chemical group 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
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- 150000003014 phosphoric acid esters Chemical class 0.000 description 8
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- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- 238000009835 boiling Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 238000005469 granulation Methods 0.000 description 4
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- 239000010954 inorganic particle Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000010422 painting Methods 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
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- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
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- 229920000178 Acrylic resin Polymers 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DEBAKWBAUARYEA-UHFFFAOYSA-N C1=CC=CC=C1C1=CC=CC=C1.CC1=CC(C)=C(C(=O)[PH2]=O)C(C)=C1 Chemical compound C1=CC=CC=C1C1=CC=CC=C1.CC1=CC(C)=C(C(=O)[PH2]=O)C(C)=C1 DEBAKWBAUARYEA-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical class C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 3
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- 125000006267 biphenyl group Chemical group 0.000 description 3
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 230000000254 damaging effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- 239000005357 flat glass Substances 0.000 description 3
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 3
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- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
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- 230000003750 conditioning effect Effects 0.000 description 2
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- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
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- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 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
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
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- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D139/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
- C09D139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/32—Radiation-absorbing paints
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- 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
- C09D7/48—Stabilisers against degradation by oxygen, light or heat
-
- 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
- C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
-
- 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
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/22—Esters containing nitrogen
- C08F222/225—Esters containing nitrogen the ester chains containing seven or more carbon atoms
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- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
- Laminated Bodies (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
一种光固化性组合物和由该光固化性组合物构成的硬涂剂,所述光固化性组合物含有下述通式(1)表示的紫外线吸收剂中的一种以上。(式中,R1~R3相互可以相同也可以不同,表示被(甲基)丙烯酰氧基取代的C1~20的支链或直链的烷基。该烷基也可以用羟基、C1~8的烷氧基、C1~8的酰氧基取代。而且,所述烷基也可以被氧原子、硫原子、羰基、酯基、酰胺基、酰亚胺基中的1个以上中断。R4~R6相互可以相同也可以不同,表示氢原子、卤原子、羟基、碳原子数为1~12的烷基、碳原子数为1~12的烷氧基,
Description
技术领域
本发明涉及含有紫外线吸收剂的光固化性组合物。另外,还涉及由该光固化性组合物构成的硬涂剂。
背景技术
近年来,作为信息处理装置的输入装置,已知设置于图像显示装置的画面上的、根据按压画面的位置来对信息处理装置给出规定指示的触摸面板。在以安装有触摸面板的图像显示装置为代表的多数图像显示装置的使用者侧的最表面,设置有防止损伤的硬涂膜。
另外,随着手机和笔记本型电脑、PDA(便携信息终端)等便携型信息设备的普及,图像显示装置在屋外使用的机会变多。屋外用途的图像显示装置的硬涂膜必须对紫外线有优良的耐性,即,即使长时间暴露于紫外线中也不会发生黄变,并且硬涂层与基材膜之间不会发生剥离。
不仅为了保护上述的屋外用途的触摸面板和图像显示装置,还为了保护建筑物或车辆的窗玻璃用的保护膜或遮光膜等塑料成型物或涂装物的表面、得到耐擦伤性、耐污染性优良的表面,一直采用的是形成硬涂膜。可是,这些硬涂膜如果长时间接受紫外线,硬涂膜本身就会劣化,渐渐地在硬涂膜上发生剥离、龟裂、变色等。为了防止这样的劣化,进行了在硬涂膜中添加紫外线吸收剂以提高对紫外线的耐久性等各种努力。
如果使用有机系树脂组合物作为形成硬涂层的材料,则能够通过涂布等简便地形成硬涂层,因而是优选的,但如果使用热固性树脂作为树脂,则为了使硬涂层固化就必须加热。可是,当基材是薄的膜时,由于加热会引起变形等,所以不希望加热。因此,通常使用可通过紫外线固化的紫外线固化性树脂等光固化性树脂作为构成硬涂膜的硬涂层的树脂。
可是,当使用紫外线固化性树脂作为构成硬涂层的树脂时,由于添加的紫外线吸收剂的影响,存在着涂膜硬度变得不足,或聚对苯二甲酸乙二醇酯等基材膜与硬涂膜的密合性下降的问题。
因此,在专利文献1中,提出了一种通过在基材膜上形成硬涂层而构成的硬涂膜,所述硬涂层含有具有可自由基聚合的(甲基)丙烯酸系官能团的紫外线吸收剂、例如苯并三唑系化合物。此时记载有:能够在不损害硬涂层的硬度的情况下含有大量的紫外线吸收剂,并且能够实现兼备高的硬度和优良的紫外线吸收性能的硬涂层。可是,苯并三唑系的紫外线吸收剂无论其吸收波长还是吸收性能都不能满足,其效果并不充分。
另一方面,在专利文献2中,提出了一种具有(甲基)丙烯酰基的三嗪系紫外线吸收剂。但其中没有记载在光固化性组合物中的应用,不能获得该认识。
现有技术文献
专利文献
专利文献1:日本特开2007-230093号公报
专利文献2:日本特开平11-71355号公报
发明内容
本发明要解决的问题
因此,本发明的目的是提供一种具有优良的紫外线固化性的光固化性组合物。进而提供一种由该光固化性组合物构成的、硬度和与基材的密合性优良的硬涂剂。
解决问题的手段
本发明人为了解决上述课题而进行了深入研究,结果发现了具有(甲基)丙烯酰氧基的三嗪系紫外线吸收剂,从而完成了本发明。
即,本发明提供一种光固化性组合物,其含有下述通式(1)表示的紫外线吸收剂中的一种以上。
(式中,R1~R3相互可以相同也可以不同,表示被(甲基)丙烯酰氧基取代的碳原子数为1~20的支链或直链的烷基。该烷基也可以被羟基、碳原子数为1~8的烷氧基、碳原子数为1~8的酰氧基取代。而且,所述烷基也可以被氧原子、硫原子、羰基、酯基、酰胺基、酰亚胺基中的1个以上中断。R4~R6相互可以相同也可以不同,表示氢原子、卤原子、羟基、碳原子数为1~12的烷基、碳原子数为1~12的烷氧基。)
另外,本发明提供一种光固化性组合物,其进一步含有选自光固化性单体、光固化性低聚物、光固化性聚合物中的一种以上、以及光聚合引发剂中的一种以上。
另外,本发明提供一种上述光固化性组合物,其中,光固化性单体、光固化性低聚物和光固化性聚合物是具有(甲基)丙烯酰基的化合物。
另外,本发明提供一种硬涂剂,其由上述固化性组合物构成。
另外,本发明提供一种硬涂膜,其包括硬涂层,所述硬涂层是使用上述硬涂剂在基材膜上形成的。
发明的效果
根据本发明,可以提供一种具有优良的紫外线固化性的光固化性组合物。另外,可以提供一种硬度和与基材的密合性优良的紫外线固化性的硬涂剂。
附图说明
图1是合成例1中得到的化合物No.2的吸收光谱。
图2是合成例2中得到的紫外线吸收剂混合物-1的吸收光谱。
具体实施方式
下面对本发明进行详细描述。
本发明的光固化性组合物含有下述通式(1)表示的紫外线吸收剂中的一种以上。
(式中,R1~R3相互可以相同也可以不同,表示被(甲基)丙烯酰氧基取代的碳原子数为1~20的支链或直链的烷基。该烷基也可以被羟基、碳原子数为1~8的烷氧基、碳原子数为1~8的酰氧基取代。而且,所述烷基也可以被氧原子、硫原子、羰基、酯基、酰胺基、酰亚胺基中的1个以上中断。R4~R6相互可以相同也可以不同,表示氢原子、卤原子、羟基、碳原子数为1~12的烷基、碳原子数为1~12的烷氧基。)
在通式(1)中,(甲基)丙烯酰氧基是指由下述通式(2)表示的基团,是通式(2)的R7为氢原子时的丙烯酰氧基或R7为甲基时的甲基丙烯酰氧基。
(式中,R7表示氢原子或甲基。)
另外,在通式(1)中,碳原子数为1~20的支链或直链的烷基可以列举出例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、叔戊基、1,2-二甲基丙基、正己基、环己基、1,3-二甲基丁基、1-异丙基丙基、1,2-二甲基丁基、正庚基、2-庚基、1,4-二甲基戊基、叔庚基、2-甲基-1-异丙基丙基、1-乙基-3-甲基丁基、正辛基、叔辛基、2-乙基己基、2-甲基己基、2-丙基己基、正壬基、异壬基、正癸基、异癸基、正十一烷基、异十一烷基、正十二烷基、异十二烷基、正十三烷基、异十三烷基、正十四烷基、异十四烷基、正十五烷基、异十五烷基、正十六烷基、异十六烷基、正十七烷基、异十七烷基、正十八烷基、异十八烷基、正十九烷基、异十九烷基、正二十烷基、异二十烷基等。该烷基也可以被氧原子、硫原子、羰基、酯基、酰胺基、酰亚胺基中的1个以上中断。
另外,基于(甲基)丙烯酰基的取代位置可以是上述碳原子数为1~20的支链或直链的烷基的任何位置。
另外,在通式(1)中,作为在被(甲基)丙烯酰氧基取代的碳原子数为1~20的支链或直链的烷基上的、可以取代的碳原子数为1~8的烷氧基的例子,可以列举出与上述碳原子数为1~20的支链或直链的烷基的例子中的、碳原子数为1~8的烷基对应的烷氧基。
另外,在通式(1)中,作为在被(甲基)丙烯酰氧基取代的碳原子数为1~20的支链或直链的烷基上的、可以取代的碳原子数为1~8的酰氧基的例子,可以列举出与上述碳原子数为1~20的支链或直链的烷基的例子中的、碳原子数为1~8的烷基对应的酰氧基。
另外,在通式(1)中,作为R4~R6所表示的碳原子数为1~12的烷基的例子,可以列举出上述碳原子数为1~20的支链或直链的烷基的例子中的、碳原子数为1~12的烷基。
另外,在通式(1)中,作为R4~R6所表示的碳原子数为1~12的烷氧基的例子,可以列举出与上述碳原子数为1~20的支链或直链的烷基的例子中的、碳原子数为1~12的烷基对应的烷氧基。
另外,从紫外线吸收性能的观点出发,R1~R3优选为被(甲基)丙烯酰氧基取代的碳原子数为1~8的烷基。
另外,从紫外线吸收性能的观点出发,R4~R6优选氢原子。
作为本发明中使用的通式(1)表示的紫外线吸收剂的具体例子,可以列举出下述的化合物No.1~No.12,但不限于这些化合物。
本发明的光固化性组合物中的、通式(1)的紫外线吸收剂的含量优选为光固化性组合物中的固体成分(除溶剂以外的成分)的0.1~20.0质量%,更优选为0.1~10.0质量%。
通式(1)的紫外线吸收剂的含量如果低于0.1%,则不能获得满意的紫外线吸收性能,固化物的耐气候性有可能产生问题,如果超过20.0质量%,则有可能对固化物的物性产生不良影响。
下面,对本发明的通式(1)所表示的紫外线吸收剂的合成方法进行说明。
通式(1)所表示的紫外线吸收剂的合成方法没有特别限定,通常使用的合成方法均可以使用。
例如,以化合物No.1为例,在溶剂中,使2-甲基间苯二酚3摩尔与氰脲酰氯1摩尔加成,合成2,4,6-三(2,4-二羟基-3-甲基苯基)三嗪,使其与6-氯-1-己醇3摩尔反应,然后与甲基丙烯酸反应,由此可以合成2,4,6-三[2-羟基-3-甲基-4-(6-甲基丙烯酰氧基)己氧基苯基]三嗪(化合物No.1)。
本发明的光固化性组合物优选含有选自光固化性单体、光固化性低聚物、光固化性聚合物中的一种以上。
光固化性单体、光固化性低聚物和光固化性聚合物优选具有一个以上的可自由基聚合的官能团,更优选具有一个以上的(甲基)丙烯酸系的官能团(例如(甲基)丙烯酰基)的(甲基)丙烯酸酯化合物。本发明的光固化性组合物中的、光固化性单体、光固化性低聚物、光固化性聚合物的含量优选为光固化性组合物中的固体成分(除溶剂以外的成分)的80~95质量%。
作为(甲基)丙烯酸酯化合物,可以列举出例如(甲基)丙烯酸乙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸壬酯、(甲基)丙烯酸十三碳烷酯、(甲基)丙烯酸十六碳烷酯、(甲基)丙烯酸十八碳烷酯、(甲基)丙烯酸异戊酯、(甲基)丙烯酸异癸酯、(甲基)丙烯酸异硬脂酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸2-羟基乙酯、(甲基)丙烯酸3-氯-2-羟基丙酯、(甲基)丙烯酸甲氧基乙酯、(甲基)丙烯酸丁氧基乙酯、(甲基)丙烯酸壬基苯氧基乙酯、(甲基)丙烯酸四氢糠基酯、(甲基)丙烯酸缩水甘油酯、(甲基)丙烯酸2-羟基-3-苯氧基丙酯、(甲基)丙烯酸壬基苯氧基乙基四氢糠基酯、己内酯改性(甲基)丙烯四氢糠基酯、(甲基)丙烯酸二乙基氨基乙酯、1,4-丁二醇二(甲基)丙烯酸酯、3-甲基-1,5-戊二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、2-甲基-1,8-辛二醇二(甲基)丙烯酸酯、2-丁基-2-乙基-1,3-丙二醇二(甲基)丙烯酸酯等烷二醇二(甲基)丙烯酸酯类、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、三丙二醇二(甲基)丙烯酸酯、聚丙二醇二(甲基)丙烯酸酯等聚氧烷基醚二(甲基)丙烯酸酯类、降冰片烷二甲醇二丙烯酸酯、降冰片烷二乙醇二(甲基)丙烯酸酯、在降冰片烷二甲醇上加成了环氧乙烷或环氧丙烷2摩尔而得到的二醇的二(甲基)丙烯酸酯、5-乙基-5-羟基甲基-β,β-二甲基-1-1,3-二噁烷-2-乙醇二丙烯酸酯、三环癸烷二甲醇二(甲基)丙烯酸酯、三环癸烷二乙醇二(甲基)丙烯酸酯、在三环癸烷二甲醇上加成了环氧乙烷或环氧丙烷2摩尔而得到的二醇的二(甲基)丙烯酸酯、五环十五烷二甲醇二(甲基)丙烯酸酯、五环十五烷二乙醇二(甲基)丙烯酸酯、在五环十五烷二甲醇上加成了环氧乙烷或环氧丙烷2摩尔的二醇的二(甲基)丙烯酸酯、在五环十五烷二乙醇上加成了环氧乙烷或环氧丙烷2摩尔的二醇的二(甲基)丙烯酸酯等具有脂环式结构的二醇二(甲基)丙烯酸酯类、双(2-丙烯酰氧基乙基)羟基乙基异氰脲酸酯、双(2-丙烯酰氧基丙基)羟基丙基异氰脲酸酯、双(2-丙烯酰氧基丁基)羟基丁基异氰脲酸酯、双(2-甲基丙烯酰氧基乙基)羟基乙基异氰脲酸酯、双(2-甲基丙烯酰氧基丙基)羟基丙基异氰脲酸酯、双(2-甲基丙烯酰氧基丁基)羟基丁基异氰脲酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、三(2-丙烯酰氧基乙基)异氰脲酸酯、三(2-丙烯酰氧基丙基)异氰脲酸酯、三(2-丙烯酰氧基丁基)异氰脲酸酯、三(2-甲基丙烯酰氧基乙基)异氰脲酸酯、三(2-甲基丙烯酰氧基丙基)异氰脲酸酯、三(2-甲基丙烯酰氧基丁基)异氰脲酸酯、二季戊四醇的聚(甲基)丙烯酸酯、环氧乙烷改性磷酸(甲基)丙烯酸酯、环氧乙烷改性烷基化磷酸(甲基)丙烯酸酯、氨基甲酸酯(甲基)丙烯酸酯、多官能氨基甲酸酯(甲基)丙烯酸酯、环氧(甲基)丙烯酸酯、聚醚骨架的氨基甲酸酯(甲基)丙烯酸酯、聚酯骨架的氨基甲酸酯(甲基)丙烯酸酯、聚碳酸酯骨架的氨基甲酸酯(甲基)丙烯酸酯的多元醇与(甲基)丙烯酸酯化而得到的聚酯(甲基)丙烯酸酯、聚醚骨架的多元醇与(甲基)丙烯酸酯化而得到的聚醚(甲基)丙烯酸酯等。
上述氨基甲酸酯(甲基)丙烯酸酯是具有一个丙烯酰基或甲基丙烯酰基、并且具有一个以上的氨基甲酸酯键的(-NHCOO-)的化合物。另外,上述氨基甲酸酯(甲基)丙烯酸酯例如是多元醇类与聚异氰酸酯类与具有羟基的(甲基)丙烯酸酯的反应物。这里,作为多元醇类,可以列举出乙二醇、1,4-丁二醇、新戊二醇、聚己内酯多元醇、聚酯多元醇、聚碳酸酯二醇、聚丁二醇等。另外,作为聚异氰酸酯类,可以列举出六亚甲基二异氰酸酯、异佛尔酮二异氰酸酯、甲苯二异氰酸酯、苯二甲基二异氰酸酯、4,4’-二苯基甲烷二异氰酸酯等。另外,作为具有羟基的(甲基)丙烯酸酯,可以列举出(甲基)丙烯酸2-羟基乙酯、(甲基)丙烯酸2-羟基丙酯、1,4-丁二醇单(甲基)丙烯酸酯、(甲基)丙烯酸2-羟基乙酯的ε-己内酯加成物等。
上述多官能氨基甲酸酯(甲基)丙烯酸酯是具有多个丙烯酰基或甲基丙烯酰基、并且具有一个以上的氨基甲酸酯键(-NHCOO-)的化合物。另外,上述多官能氨基甲酸酯(甲基)丙烯酸酯例如是具有羟基的多官能(甲基)丙烯酸酯与聚异氰酸酯类的反应物。这里,作为具有羟基的多官能(甲基)丙烯酸酯,可以列举出例如季戊四醇三(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、三季戊四醇七(甲基)丙烯酸酯等。另一方面,作为聚异氰酸酯类,可以列举出甲苯二异氰酸酯、异佛尔酮二异氰酸酯、苯二甲基二异氰酸酯、六亚甲基二异氰酸酯等。
作为上述环氧(甲基)丙烯酸酯,例如是聚环氧化合物与(甲基)丙烯酸的反应物。这里,聚环氧化合物优选聚缩水甘油基化合物。具体地,可以列举出双酚A型环氧树脂、双酚F型环氧树脂、线性酚醛清漆型环氧树脂、三苯酚甲烷型环氧树脂、聚乙二醇二缩水甘油醚、丙三醇聚缩水甘油醚、三羟甲基丙烷聚缩水甘油醚等。
另外,本发明的光固化性组合物中,作为自由基聚合性化合物,除(甲基)丙烯酸酯化合物以外,还可以使用N-乙烯基吡咯烷酮、N-乙烯基己内酰胺、乙烯基醚单体等。
本发明的光固化性组合物优选含有一种以上的光聚合引发剂。光聚合引发剂是通过照射紫外线而产生光自由基,并具有引发上述的(甲基)丙烯酸酯化合物等光固化性单体、光固化性低聚物、光固化性聚合物的聚合的作用。
作为光聚合引发剂,可以列举出例如下述的化合物。
(1)二苯甲酮衍生物:例如二苯甲酮、O-苯甲酰苯甲酸甲酯、4-苯甲酰-4’-甲基二苯基酮、二苄基酮、芴酮
(2)苯乙酮衍生物:例如2,2’-二乙氧基苯乙酮、2-羟基-2-甲基苯丙酮、2,2-二甲氧基-1,2-二苯基乙烷-1-酮(例如BASF公司制、IRGACURE 651)、1-羟基环己基苯基酮(例如BASF公司制、IRGACURE184、DKSH Japan公司制、Esacure KS300)、2-甲基-1-[4-(甲硫基)苯基]-2-吗啉代丙烷-1-酮(例如BASF公司制、IRGACURE 907)、2-羟基-1-{4-[4-(2-羟基-2-甲基丙酰基)-苄基]-苯基}-2-甲基丙烷-1-酮(例如BASF公司制、IRGACURE 127)、苯基乙醛酸甲酯
(3)噻吨酮衍生物:例如噻吨酮、2-甲基噻吨酮、2-异丙基噻吨酮、4-异丙基噻吨酮、2-氯噻吨酮、二乙基噻吨酮
(4)苯偶酰衍生物:例如苯偶酰、苯偶酰二甲基缩酮、苯偶酰-β-甲氧基乙基缩醛
(5)苯偶姻衍生物:例如苯偶姻、苯偶姻甲基醚、2-羟基-2-甲基-1-苯基丙烷-1-酮(例如BASF公司制、DAROCURE 1173)
(6)肟系化合物:例如1-苯基-1,2-丁二酮-2-(O-甲氧基羰基)肟、1-苯基-1,2-丙二酮-2-(O-甲氧基羰基)肟、1-苯基-1,2-丙二酮-2-(O-乙氧基羰基)肟、1-苯基-1,2-丙二酮-2-(O-苯甲酰)肟、1,3-二苯基丙三酮-2-(O-乙氧基羰基)肟、1-苯基-3-乙氧基丙三酮-2-(O-苯甲酰)肟1,2-辛二酮,1-[4-(苯硫基)-2-(O-苯甲酰肟)]乙酮(例如BASF公司制、IRGACURE OXE01)、1-[9-乙基-6-(2-甲基苯甲酰基)-9H-咔唑-3-基]-1-(O-乙酰肟)(例如BASF公司制、IRGACURE OXE02)
(7)α-羟基酮系化合物:例如2-羟基-2-甲基-1-苯基丙烷-1-酮、1-[4-(2-羟基乙氧基)苯基]-2-羟基-2-甲基-1-丙烷-1-酮、2-羟基-1-{4-[4-(2-羟基-2-甲基丙酰基)-苄基]苯基}-2-甲基丙烷
(8)α-氨基烷基苯酮系化合物:例如2-苄基-2-二甲基氨基-1-(4-吗啉代苯基)-丁酮-1(例如BASF公司制、IRGACURE 369)、2-二甲基氨基-2-(4-甲基苄基)-1-(4-吗啉-4-基-苯基)丁烷-1-酮(例如BASF公司制、IRGACURE 379)
(9)氧化膦系化合物:例如双(2,4,6-三甲基苯甲酰基)-苯基氧化膦(例如BASF公司制、IRGACURE 819)、双(2,6-二甲氧基苯甲酰基)-2,4,4-三甲基-戊基氧化膦、2,4,6-三甲基苯甲酰基-二苯基-氧化膦(例如BASF公司制、DAROCURE TPO)
(10)二茂钛化合物:例如双(η5-2,4-环戊二烯-1-基)-双(2,6-二氟-3-(1H-吡咯-1-基)苯基)钛(Ciba Specialty Chemicals公司制、IRGACURE 784)
上述光聚合引发剂的含量优选为光固化性组合物的固体成分(除溶剂以外的成分)中的0.1~10质量%,更优选为0.1~5质量%,最优选为0.1~1质量%。如果低于0.1质量%,则有可能固化变得不充分,如果超过10质量%,则有可能对固化物的物性产生不良影响。
另外,本发明的光固化性组合物中,与上述光聚合引发剂一起还可以并用固化促进剂(增感剂)。作为能够并用的固化促进剂(增感剂),可以列举出例如三乙醇胺、二乙醇胺、N-甲基二乙醇胺、2-甲基氨基乙基苯甲酸酯、二甲基氨基苯乙酮、对二甲基氨基苯甲酸异戊基酯、对二甲基氨基苯甲酸乙基酯等胺类、2-巯基苯并噻唑等供氢体,作为色素增感剂,可以列举出呫吨、噻吨、香豆素、硫代香豆素等。
另外,本发明的光固化性组合物中,在不损害本发明的效果的范围内还可以配合通式(1)以外的紫外线吸收剂。
作为上述紫外线吸收剂,例如可以列举出例如2,4-二羟基二苯甲酮、2-羟基-4-甲氧基二苯甲酮、2-羟基-4-辛氧基二苯甲酮、5,5’-亚甲基双(2-羟基-4-甲氧基二苯甲酮)等2-羟基二苯甲酮类;2-(2’-羟基-5’-甲基苯基)苯并三唑、2-(2’-羟基-3’,5’-二叔丁基苯基)-5-氯苯并三唑、2-(2’-羟基-3’-叔丁基-5’-甲基苯基)-5-氯苯并三唑、2-(2’-羟基-5’-叔辛基苯基)苯并三唑、2-(2’-羟基-3’,5’-二枯基苯基)苯并三唑、2,2’-亚甲基双(4-叔辛基-6-(苯并三唑基)苯酚)、2-(2’-羟基-3’-叔丁基-5’-羧苯基)苯并三唑等2-(2’-羟基苯基)苯并三唑类;水杨酸苯酯、间苯二酚单苯甲酸酯、2,4-二叔丁基苯基-3,5-二叔丁基-4-羟基苯甲酸酯、2,4-二叔戊基苯基-3,5-二叔丁基-4-羟基苯甲酸酯、十六烷基-3,5-二叔丁基-4-羟基苯甲酸酯等苯甲酸酯类;2-乙基-2’-乙氧基草酰替苯胺、2-乙氧基-4’-十二烷基草酰替苯胺等取代草酰替苯胺类;乙基-α-氰基-β,β-二苯基丙烯酸酯、甲基-2-氰基-3-甲基-3-(对甲氧基苯基)丙烯酸酯等氰基丙烯酸酯类;2-(2-羟基-4-辛氧基苯基)-4,6-双(2,4-二叔丁基苯基)-s-三嗪、2-(2-羟基-4-甲氧基苯基)-4,6-二苯基-s-三嗪、2-(2-羟基-4-丙氧基-5-甲基苯基)-4,6-双(2,4-二叔丁基苯基)-s-三嗪等三芳基三嗪类。
另外,本发明的光固化性组合物中,在不损害本发明的效果的范围内还可以配合受阻胺系光稳定剂。
作为上述受阻胺系光稳定剂,可以列举出例如2,2,6,6-四甲基-4-哌啶基硬脂酸酯、1,2,2,6,6-五甲基-4-哌啶基硬脂酸酯、2,2,6,6-四甲基-4-哌啶基苯甲酸酯、双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、双(1,2,2,6,6-四甲基-4-哌啶基)癸二酸酯、双(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯、四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯、四(1,2,2,6,6-五甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯、双(2,2,6,6-四甲基-4-哌啶基)-二(十三烷基)-1,2,3,4-丁烷四羧酸酯、双(1,2,2,6,6-五甲基-4-哌啶基)-二(十三烷基)-1,2,3,4-丁烷四羧酸酯、双(1,2,2,4,4-五甲基-4-哌啶基)-2-丁基-2-(3,5-二叔丁基-4-羟基苄基)丙二酸酯、1-(2-羟基乙基)-2,2,6,6-四甲基-4-哌啶醇/琥珀酸二乙酯缩聚物、1,6-双(2,2,6,6-四甲基-4-哌啶基氨基)己烷/2,4-二氯-6-吗啉代-s-三嗪缩聚物、1,6-双(2,2,6,6-四甲基-4-哌啶基氨基)己烷/2,4-二氯-6-叔辛基氨基-s-三嗪缩聚物、1,5,8,12-四〔2,4-双(N-丁基-N-(2,2,6,6-四甲基-4-哌啶基)氨基)-s-三嗪-6-基〕-1,5,8,12-四氮杂十二烷、1,5,8,12-四〔2,4-双(N-丁基-N-(1,2,2,6,6-五甲基-4-哌啶基)氨基)-s-三嗪-6-基〕-1,5,8-12-四氮杂十二烷、1,6,11-三〔2,4-双(N-丁基-N-(2,2,6,6-四甲基-4-哌啶基)氨基)-s-三嗪-6-基〕氨基十一烷、1,6,11-三〔2,4-双(N-丁基-N-(1,2,2,6,6-五甲基-4-哌啶基)氨基)-s-三嗪-6-基〕氨基十一碳烷等受阻胺化合物。
另外,本发明的光固化性组合物中,为了对固化的膜(例如合成树脂膜上涂布的硬涂膜)赋予防眩性,还可以配合固体微粒。
作为固体微粒,可以列举出无机微粒和有机微粒。
作为无机微粒,可以列举出体积平均粒径为0.01~5μm的微粒、例如炭黑、二氧化硅(微粉硅酸、含水硅酸、硅藻土、胶体氧化硅等)、硅酸盐(滑石等)、碳酸盐(沉降性碳酸钙、碳酸镁等)、粘土、氧化铝(水合物)、硫酸钡(重晶石粉、沉降性硫酸钡、锌钡白等)、石膏、铅白、云母、氧化锌、氧化钛、微球(砂(shirasu)、玻璃等)等,上述无机微粒也可以并用2种以上。
无机微粒的形状可以是球状、针状、花瓣状或不定形状等,微粒的内部可以是中空状或多孔质状等,可以是通过干式造粒而得到的微粒,也可以是通过湿式造粒而得到的微粒。
作为有机微粒,可以列举出偶氮颜料、多环式颜料和有机树脂珠粒(用库尔特计数法得到的体积平均粒径为0.1~2μm的丙烯酸酯珠粒、聚苯乙烯珠粒、聚氨酯珠粒、环氧树脂珠粒等)。这些有机微粒也可以并用2种以上。
有机微粒的形状可以是球状、针状、花瓣状或不定形状等,微粒的内部可以是中空状或多孔质状等,可以是通过干式造粒而得到的微粒,也可以是通过湿式造粒而得到的微粒。
从固化涂膜的防眩性的观点出发,固体微粒的形状优选内部是中空状或多孔质状的,球状也是优选的。
另外,当配合固体微粒时,还可以配合分散剂。作为分散剂,可以列举出高分子有机分散剂、低分子有机分散剂和无机分散剂。
作为高分子有机分散剂,可以列举出萘磺酸盐的甲醛缩合物、聚苯乙烯磺酸盐、聚丙烯酸盐、羧甲基纤维素、聚羧酸盐、聚乙烯醇等。
作为低分子有机分散剂,可以列举出聚氧化亚烷基二醇型分散剂、多元醇型分散剂、羧酸盐型分散剂、硫酸酯型分散剂、磺酸盐型分散剂、磷酸酯型分散剂、伯~叔胺盐型分散剂和季铵盐型分散剂等。
作为无机分散剂,可以列举出多磷酸盐、磷酸等磷酸化合物。
另外,本发明的光固化性组合物中还可以配合消泡剂。
作为消泡剂,可以列举出例如低级醇(C1~4、例如甲醇、丁醇)、高级醇(C6~30、例如辛醇、十六碳醇)、脂肪酸(C4~30、例如油酸、硬脂酸)、脂肪酸酯(C7~36、例如丙三醇单月桂酸酯)、磷酸酯(C6~20、例如磷酸三丁酯)、金属皂(C18~30、例如硬脂酸钙、硬脂酸铝)、矿物油、聚醚(例如PEG、PPG)、硅酮(例如二甲基硅油、烷基改性硅油、氟代硅油)等。
另外,本发明的光固化性组合物中还可以配合硅烷偶联剂。
作为硅烷偶联剂,可以列举出胺系化合物(γ-氨基丙基三乙氧基硅烷、γ-氨基丙基三甲氧基硅烷、γ-苯基氨基丙基三甲氧基硅烷等)、脲基系化合物(脲基丙基三乙氧基硅烷等)、乙烯基化合物(乙烯基乙氧基硅烷、乙烯基甲氧基硅烷、乙烯基三(β-甲氧基乙氧基)硅烷等)、甲基丙烯酸酯系化合物(γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-甲基丙烯酰氧基丙基甲基二甲氧基硅烷等)、环氧系化合物(γ-环氧丙氧基丙基三甲氧基硅烷等)、异氰酸酯系化合物(γ-异氰酸酯丙基三乙氧基硅烷等)、聚合物型(聚甲氧基二甲基硅氧烷、聚乙氧基二甲基硅氧烷等)、阳离子型(N-(N-苄基-β-氨基乙基)-γ-氨基丙基三甲氧基硅烷盐酸盐等)等硅烷偶联剂。
另外,本发明的光固化性组合物中还可以配合触变性赋予剂(增稠剂)。
作为触变性赋予剂(增稠剂),可以列举出例如无机触变性赋予剂(增稠剂)(膨润土、有机处理膨润土、极微细表面处理碳酸钙等)、有机触变性赋予剂(增稠剂)(氢化蓖麻油蜡、硬脂酸钙、油酸铝、聚合亚麻仁油等)等。
另外,本发明的光固化性组合物中,根据需要还可以配合酚系抗氧化剂、磷系抗氧化剂、硫醚系抗氧化剂等合成树脂中使用的添加剂以实现稳定化。
作为上述酚系抗氧化剂,例如2,6-二叔丁基-对甲酚、2,6-二苯基-4-十八烷氧基苯酚、二硬脂酰基(3,5-二叔丁基-4-羟基苄基)膦酸酯、1,6-六亚甲基双〔(3,5-二叔丁基-4-羟基苯基)丙酰胺〕、4,4’-硫代双(6-叔丁基-间甲酚)、2,2’-亚甲基双(4-甲基-6-叔丁基苯酚)、2,2’-亚甲基双(4-乙基-6-叔丁基苯酚)、4,4’-丁叉双(6-叔丁基-间甲酚)、2,2’-乙叉双(4,6-二叔丁基苯酚)、2,2’-乙叉双(4-仲丁基-6-叔丁基苯酚)、1,1,3-三(2-甲基-4-羟基-5-叔丁基苯基]丁烷、1,3,5-三(2,6-二甲基-3-羟基-4-叔丁基苄基)异氰脲酸酯、1,3,5-三(3,5-二叔丁基-4-羟基苄基)异氰脲酸酯、1,3,5-三(3,5-二叔丁基-4-羟基苄基)-2,4,6-三甲基苯、2-叔丁基-4-甲基-6-(2-丙烯酰氧基-3-叔丁基-5-甲基苄基)苯酚、硬脂酰基(3,5-二叔丁基-4-羟基苯基)丙酸酯、四〔3-(3,5-二叔丁基-4-羟基苯基)丙酸甲酯〕甲烷、硫代二乙二醇双〔(3,5-二叔丁基-4-羟基苯基)丙酸酯〕、1,6-六亚甲基双〔(3,5-二叔丁基-4-羟基苯基)丙酸酯〕、双[3,3-双(4-羟基-3-叔丁基苯基)丁酸]二醇酯、双[2-叔丁基-4-甲基-6-(2-羟基-3-叔丁基-5-甲基苄基)苯基]对苯二甲酸酯、1,3,5-三[(3,5-二叔丁基-4-羟基苯基)丙酰氧基乙基]异氰脲酸酯、3,9-双[1,1-二甲基-2-{(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基}乙基]-2,4,8,10-四氧杂螺[5,5]十一烷、三乙二醇双[(3-叔丁基-4-羟基-5-甲基苯基)丙酸酯]等。
作为上述磷系抗氧化剂,可以列举出例如三壬基苯基亚磷酸酯、三[2-叔丁基-4-(3-叔丁基-4-羟基-5-甲基苯硫基)-5-甲基苯基]亚磷酸酯、亚磷酸三癸酯、辛基二苯基亚磷酸酯、二癸基单苯基亚磷酸酯、二(十三烷基)季戊四醇二亚磷酸酯、二(壬基苯基)季戊四醇二亚磷酸酯、双(2,4-二叔丁基苯基)季戊四醇二亚磷酸酯、双(2,6-二叔丁基-4-甲基苯基)季戊四醇二亚磷酸酯、双(2,4,6-三叔丁基苯基)季戊四醇二亚磷酸酯、双(2,4-二枯基苯基)季戊四醇二亚磷酸酯、四(十三烷基)异丙叉二苯酚二亚磷酸酯、四(十三烷基)-4,4’-正丁叉双(2-叔丁基-5-甲基苯酚)二亚磷酸酯、六(十三烷基)-1,1,3-三(2-甲基-4-羟基-5-叔丁基苯基)丁烷三亚磷酸酯、四(2,4-二叔丁基苯基)联苯撑二膦酸酯、9,10-二氢-9-氧代-10-磷杂菲-10-氧化物、2,2’-亚甲基双(4,6-叔丁基苯基)-2-乙基己基亚磷酸酯、2,2’-亚甲基双(4,6-叔丁基苯基)-十八烷基亚磷酸酯、2,2’-乙叉双(4,6-二叔丁基苯基)氟代亚磷酸酯、三(2-[(2,4,8,10-四叔丁基二苯并[d,f][1,3,2]二噁磷环庚烷-6-基)氧]乙基)胺、2-乙基-2-丁基丙二醇和2,4,6-三叔丁基苯酚的亚磷酸酯等。
作为上述硫醚系抗氧化剂,可以列举出例如硫代二丙酸二月桂酯、硫代二丙酸二肉豆蔻酯、硫代二丙酸二硬脂酯等二烷基硫代二丙酸酯类以及季戊四醇四(β烷基硫代丙酸酯)类。
另外,本发明的光固化性组合物中,根据需要还可以配合合成树脂中使用的磷酸酯系阻燃剂、缩合磷酸酯系阻燃剂、(多)磷酸盐系阻燃剂等阻燃剂。
作为上述磷酸酯系阻燃剂的例子,可以列举出例如磷酸三甲酯、磷酸三乙酯、磷酸三丁酯、三丁氧基乙基磷酸酯、三氯代乙基磷酸酯、三(二氯丙基)磷酸酯、磷酸三苯酯、磷酸三甲苯酯、甲苯基二苯基磷酸酯、三(二甲苯基)磷酸酯、辛基二苯基磷酸酯、二甲苯基二苯基磷酸酯、三异丙基苯基磷酸酯、2-乙基己基二苯基磷酸酯、叔丁基苯基二苯基磷酸酯、双(叔丁基苯基)苯基磷酸酯、三-(叔丁基苯基)磷酸酯、异丙基苯基二苯基磷酸酯、双-(异丙基苯基)二苯基磷酸酯、三-(异丙基苯基)磷酸酯等。
作为上述缩合磷酸酯系阻燃剂的例子,可以列举出1,3-亚苯基双(二苯基磷酸酯)、1,3-亚苯基双(二(二甲苯基)磷酸酯)、双酚A双(二苯基磷酸酯)等。
作为上述(多)磷酸盐系阻燃剂的例子,可以列举出多磷酸铵、多磷酸三聚氰胺、多磷酸哌嗪、焦磷酸三聚氰胺、焦磷酸哌嗪等(多)磷酸的铵盐或胺盐。
进而,在本发明的光固化性组合物中,根据需要还可以配合流平剂(例如氟系化合物、硅酮系化合物、丙烯酸系化合物等)、着色剂(颜料、染料等)、交联剂(聚异氰酸酯类、三聚氰胺类等)、填充剂(二氧化硅、陶瓷粉、玻璃粉、金属粉、氧化铝、胶体氧化硅、无机填料、有机树脂填料等)等。
另外,为了涂布于基材上,还可以将本发明的光固化性组合物用有机溶稀释后使用。作为有机溶剂,可以列举出例如乙酸乙酯、乙酸丙酯、乙酸丁酯、乙酸戊酯、乙酸苄酯、乙二醇单丁基乙酸酯、乳酸丁酯、乙酰丙酸丁酯等酯系溶剂;甲乙酮、乙基丁基酮、甲基异丁基酮、环己酮等酮系溶剂;乙二醇单甲基醚、乙二醇单乙基醚、乙二醇单丁基醚、乙二醇苄基醚、乙二醇单苯基醚、丙二醇单甲基醚、丙二醇单乙基醚、苄基醇、甲基苯基卡必醇、正丁醇和叔丁醇等醇系溶剂;苯、甲苯、二甲苯、异丙基苯等芳香族系溶剂、二氯甲烷、二氯乙烷、氯苯等卤代烃系溶剂、石油醚、石脑油等石油系溶剂、正己烷、环己烷等脂肪族系溶剂。它们可以单独使用1种,也可以并用2种以上。
本发明的光固化性组合物优选作为光固化性的硬涂剂使用。
作为本发明的硬涂剂的基材,可以列举出例如聚酯(PET)、聚丙烯、聚乙烯、聚丙烯酸酯、聚碳酸酯、三乙酰纤维素、聚醚砜、环烯烃系聚合物等合成树脂的薄膜或片材,特别是优选聚酯(PET)的薄膜或片材。作为本发明的硬涂膜中使用基材膜的例子,也可以列举出上述列举的各种合成树脂的薄膜或片材。另外,这些薄膜或片材也可以实施了各种表面处理或取向处理。
作为将本发明的硬涂剂涂布于基材的树脂薄膜或片材上的方法,可以列举出例如棒涂、迈耶棒(Meyer bar coating)涂布、气刀涂布、照相凹版涂布、反向式照相凹版涂布、微型照相凹版涂布、微型反向式照相凹版涂布、模涂、浸涂、旋涂、喷涂等,或者可以列举出印刷法(照相凹版印刷、反向式照相凹版印刷、胶版印刷、柔性印刷、丝网印刷等)。
通过紫外线照射使本发明的光固化性组合物或硬涂剂固化时,使用具有氙灯、高压水银灯、金属卤化物灯等作为光源的紫外线照射装置,紫外线的照射量等适当调节即可。
当使用本发明的光固化性组合物作为硬涂剂时,具有硬度、耐擦伤性、与基材膜的密合性、耐气候性优良的特征。
本发明的光固化性组合物优选作为硬涂剂使用,涂布了该硬涂剂的合成树脂薄膜或片材由于具有优良的硬度、耐擦伤性、透明性、外观、耐气候性等,所以在用于以液晶显示装置为代表的显示器的光学膜等中是有用的。具体地,可以用于手机、智能手机、电脑、PDA(便携信息终端)等,特别是对于它们的触摸面板是有用的。
此外,作为本发明的光固化性组合物或硬涂剂的用途,可以列举出例如电脑用材料(笔输入式电脑、触摸面板、显示器罩等)、家电制品(电视、收录机、立体音响设备、电脑游戏机的罩或显示器等)、汽车用材料(前灯、玻璃窗(glazing)、仪表类的罩等)、光盘、光学用透镜(照相机、摄像机、放大镜等)、眼镜透镜(矫正用、太阳镜、时尚眼镜等)、体育用品(滑雪板、网球拍等)、有机板玻璃、看板、交通标识、铭牌、装饰用盒子、钟表用透镜、化妆品容器、住宅构件、转印箔、转印膜、干膜抗蚀剂、反射镜等。
实施例
下面,通过实施例等更具体地说明本发明,但本发明不受以下的实施例等的限制。
〔合成例1〕紫外线吸收剂(化合物No.2)的合成
首先,按照以下的步骤合成作为中间体的2,4,6-三[2-羟基-3-甲基-4-(6-羟基)己氧基苯基]三嗪(以下称作中间体A)。
在300ml的四口烧瓶中加入2,4,6-三(2,4-二羟基-3-甲基苯基)三嗪10.00g、碳酸钾5.56g、环己酮50.15g、甲苯4.18g,升温至130℃。向其中滴加6-氯-1-己醇10.99g,反应9小时。使用甲酸进行中和处理后,水洗,减压脱溶剂,使残渣在环己酮/甲苯(3/1)中重结晶,得到熔点为128℃的淡黄色粉末12.01g(收率72%)。
接着,在300ml的四口烧瓶中加入中间体A为10.00g、对甲苯磺酸一水合物0.17g、对甲氧基苯酚0.08g,升温至105℃。向其中滴加丙烯酸5.78g,反应12小时。将反应液进行水洗,减压脱溶剂后,使残渣在甲苯/异丙醇(1/1)中重结晶,得到熔点为91℃的淡黄色粉末8.15g(收率67%)。对于得到的化合物,进行1H-NMR测定。分析结果如下所示。根据下述分析结果确认:得到的粉末是化合物No.2。
1H-NMR(CDCl3)1.61-1.71(CH2CH 2CH 2CH2),1.75-1.85(CH 2CH2CH2CH 2),2.18(Ar-CH3),3.99-4.19(ArOCH2),4.06-4.26(C(=O)OCH2),5.73-5.87(CH=CH 2),5.96-6.25(CH=CH2),6.32-6.53(CH=CH 2),6.51-6.61(Ar-H),7.96-8.06(Ar-H),13.52(Ar-OH)
另外,测定得到的化合物No.2的氯仿溶液(浓度10mg/L)的吸收光谱。测定是使用日本分光株式会社制V-560来进行。吸收光谱示于图1中。最大吸收波长为356nm,摩尔吸光系数ε=1.41×10-5。
〔合成例2〕紫外线吸收剂混合物-1的合成
合成由下述结构式表示的紫外线吸收剂混合物-1。
首先,按照以下的步骤合成作为中间体的2,4,6-三(2,6-二羟基-4-甲基苯基)三嗪与碳酸亚丙酯的加成产物(以下称作中间体B)。
在1000ml的四口烧瓶中加入2,4,6-三(2,4-二羟基-3-甲基苯基)三嗪67.16g、碳酸亚丙酯122.59g、碳酸钠0.80g、环己酮466.27g,升温至160℃,反应16小时。使用甲酸进行中和处理后,减压脱溶剂,使残渣在二甲基甲酰胺/异丙醇(1/3)中重结晶,得到熔点为136℃的淡黄色粉末74.22g(收率80%)。
接着,在50ml的四口烧瓶中加入中间体B为1.50g、对甲苯磺酸一水合物0.55g、对甲氧基苯酚0.09g,升温至105℃。向其中滴加甲基丙烯酸6.23g,反应10小时。将反应液进行水洗,减压脱溶剂,从而得到熔点为118℃的淡黄色粉末0.81g(收率41%)。对于得到的化合物,进行1H-NMR测定。分析结果如下所示。根据下述分析结果确认:得到的粉末是紫外线吸收剂混合物-1。
1H-NMR(CDCl3)1.42-1.49(OCHCH 3),1.96(CH2=CCH 3),2.15(Ar-CH3),4.10-4.16(OCH2),5.29-5.48(OCHCH3),5.56-5.60(CH 2=CCH3),6.11-6.13(CH 2=CCH3),6.50-6.60(Ar-H),7.93-8.03(Ar-H),13.45(Ar-OH)
另外,测定得到的紫外线吸收剂混合物-1的氯仿溶液(浓度10mg/L)的吸收光谱。测定是使用日本分光株式会社制V-560来进行。吸收光谱示于图2中。最大吸收波长为354nm,摩尔吸光系数ε=1.34×10-5。
〔实施例1、2、比较例1~3〕光固化性组合物(硬涂剂)的制造和评价
在实施例1、2中,使用合成例1中得到的化合物No.2的紫外线吸收剂或合成例2中得到的紫外线吸收剂混合物-1,按照表1记载的配合得到作为光固化性组合物的硬涂剂。使用棒涂器将得到的硬涂剂按照使干燥固化后的厚度为5μm或10μm的方式涂布于干涉条纹对策处理PET(三菱树脂株式会社公司制的O321)上,形成皮膜层,在80℃下干燥1分钟后,对该皮膜层在氮气气氛下用紫外线照射装置(フュージョンUVシステムズ公司制的F300S)照射300mJ/cm2的紫外线。
用下述方法对得到的硬涂膜进行性能评价。评价结果示于表1中。
另外,在比较例1中,除了不使用紫外线吸收剂以外,与实施例1同样地得到硬涂膜,进行性能评价。在比较例2、3中,按照表1所示的配合量使用市售的三嗪系紫外线吸收剂Tinuvin477(BASF公司制)代替化合物No.2,除此以外,与实施例1同样地得到硬涂膜,进行性能评价。评价结果示于表1中。
〔实施例3、4、比较例4~6〕光固化性组合物(硬涂剂)的制造和评价
在实施例3、4中,将薄膜基材从干涉条纹对策处理PET变更为易粘接处理PET(东洋纺株式会社制的A-4300),除此以外,按照与实施例1同样的步骤得到硬涂膜,进行性能评价。评价结果示于表2中。另外,在比较例4中,除了不使用紫外线吸收剂以外,与实施例3同样地得到硬涂膜,进行性能评价。在比较例5、6中,按照表2所示的配合量使用市售的三嗪系紫外线吸收剂Tinuvin477(BASF公司制)代替化合物No.2,除此以外,按照与实施例3同样的步骤得到硬涂膜,进行性能评价。评价结果示于表2中。
〔实施例5、6、比较例7~9〕
在实施例5、6中,代替在氮气气氛下进行紫外线的照射,而在空气气氛下进行照射,除此以外,按照与实施例3同样的步骤得到硬涂膜,进行性能评价。评价结果示于表3中。另外,在比较例7中,除了不使用紫外线吸收剂以外,与实施例5同样地得到硬涂膜,进行性能评价。在比较例8、9中,按照表3所示的配合量使用市售的三嗪系紫外线吸收剂Tinuvin477(BASF公司制)代替化合物No.2,除此以外,按照与实施例5同样的步骤得到硬涂膜,进行性能评价。评价结果示于表3中。
<性能评价方法>
(1)Haze(雾度)
根据JIS K7105、JIS K7136测定硬涂膜的Haze值(%)。
(2)总光线透射率(透明性)
根据JIS K7105、JIS K7136测定硬涂膜的总光线透射率(%)。
(3)UV透射率
测定硬涂膜的365nm和380nm的紫外线的透射率(%)。测定是使用日本分光株式会社制V-670来进行。
(4)铅笔硬度
根据JIS K5600-5-4,使铅笔相对于涂面为45度的角度并在荷重750g下测定。
(5)密合性试验
对于硬涂膜,在硬涂层的表面用切割刀以1mm间隔划伤,制作100个格,其上面粘贴透明胶带,以60度的角度剥离透明胶带,用100个格中涂膜未剥离而留下的数量来评价。
(6)耐擦伤性试验
使用荷重变动型摩擦磨损系统(新东科学株式会社制的TRIBOGEARHHS2000),使用钢丝绒#0000,每1cm2施加2Kg的荷重来回20次,通过直接(自然光下)和绿光下的目视按照下述基准评价擦伤的状况。
评价中5分是最高,0分是最低。
5分:完全没有擦伤。
4分:看到1~5条擦伤。
3分:看到6~15条擦伤。
2分:看到16~30条擦伤。
1分:看到许多擦伤。
0分:在整个面上都看到擦伤。
(7)卷曲性
将硬涂膜切割成10cm×10cm,首先将左侧一半(相当于5cm)用玻璃板压紧,测定翘起的右侧的2角的各自的高度,然后将右侧一半(相当于5cm)用玻璃板压紧,测定翘起的左侧的2角的各自的高度,将4个测定值的平均(单位:mm)设定为卷曲性。
表1
*1:荒川化学工业株式会社制的商品名BEAM SET575CB、聚氨酯丙烯酸酯与1-羟基环己基苯基酮的混合物
*2:ETERNAL CHEMICAL公司制的商品名EM265、丙烯酸树脂
*3:株式会社ADEKA制的商品名SP-246、二苯基-(2,4,6-三甲基苯甲酰基)氧化膦
*4:DKSH Japan公司制的商品名EsacureKS300、1-羟基环己基苯基酮
*5:BYK Japan公司制的商品名BYK-375
表2
*1:荒川化学工业株式会社制的商品名BEAM SET 575CB、聚氨酯丙烯酸酯
与1-羟基环己基苯基酮的混合物
*2:ETERNAL CHEMICAL公司制的商品名EM265、丙烯酸树脂
*3:株式会社ADEKA制的商品名SP-246、二苯基-(2,4,6-三甲基苯甲酰基)氧化膦
*4:DKSH Japan公司制的商品名EsacureKS300、1-羟基环己基苯基酮
*5:BYK Japan公司制的商品名BYK-375
表3
*1:荒川化学工业株式会社制的商品名BEAM SET575CB、聚氨酯丙烯酸酯
与1-羟基环己基苯基酮的混合物
*2:ETERNAL CHEMICAL公司制的商品名EM265、丙烯酸树脂
*3:株式会社ADEKA制的商品名SP-246、二苯基-(2,4,6-三甲基苯甲酰基)氧化膦
*4:DKSH Japan公司制的商品名EsacureKS300、1-羟基环己基苯基酮
*5:BYK Japan公司制的商品名BYK-375
Claims (5)
1.一种光固化性组合物,其含有下述通式(1)表示的紫外线吸收剂中的一种以上,
式中,R1~R3相互可以相同也可以不同,表示被(甲基)丙烯酰氧基取代的碳原子数为1~20的支链或直链的烷基,所述烷基也可以被羟基、碳原子数为1~8的烷氧基、碳原子数为1~8的酰氧基取代,而且,所述烷基也可以被氧原子、硫原子、羰基、酯基、酰胺基、酰亚胺基中的1个以上中断,R4~R6相互可以相同也可以不同,表示氢原子、卤原子、羟基、碳原子数为1~12的烷基、碳原子数为1~12的烷氧基。
2.根据权利要求1所述的光固化性组合物,其进一步含有选自光固化性单体、光固化性低聚物、光固化性聚合物中的一种以上、以及光聚合引发剂中的一种以上。
3.根据权利要求2所述的光固化性组合物,其中,光固化性单体、光固化性低聚物和光固化性聚合物是具有(甲基)丙烯酰基的化合物。
4.一种硬涂剂,其由权利要求1~3中任一项所述的光固化性组合物构成。
5.一种硬涂膜,其包括硬涂层,所述硬涂层是使用权利要求4所述的硬涂剂在基材膜上形成的。
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CN110678448A (zh) * | 2017-05-25 | 2020-01-10 | 株式会社Adeka | 三嗪化合物、固化性组合物、固化物的制造方法及其固化物 |
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JP2018100347A (ja) * | 2016-12-20 | 2018-06-28 | 日本ペイントホールディングス株式会社 | 複合塗膜、複合塗膜の製造方法、物品および塗料組成物 |
CN111116822B (zh) * | 2019-12-31 | 2021-04-16 | 东莞市德聚胶接技术有限公司 | 一种丙烯酸树脂组合物 |
JP7235697B2 (ja) * | 2020-05-13 | 2023-03-08 | 大日精化工業株式会社 | 反応性紫外線吸収剤及びその製造方法、並びに紫外線・電子線硬化性コーティング剤 |
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