CN106574027B - Ultraviolet-curable resin composition and laminate using same - Google Patents
Ultraviolet-curable resin composition and laminate using same Download PDFInfo
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- CN106574027B CN106574027B CN201580043120.2A CN201580043120A CN106574027B CN 106574027 B CN106574027 B CN 106574027B CN 201580043120 A CN201580043120 A CN 201580043120A CN 106574027 B CN106574027 B CN 106574027B
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- acrylate
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- 239000011342 resin composition Substances 0.000 title claims abstract description 26
- -1 polyoxyalkylene Polymers 0.000 claims abstract description 93
- 229920000642 polymer Polymers 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 29
- 239000000178 monomer Substances 0.000 claims abstract description 27
- 239000004014 plasticizer Substances 0.000 claims abstract description 23
- 239000003999 initiator Substances 0.000 claims abstract description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 13
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 13
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical group C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229920002635 polyurethane Polymers 0.000 claims abstract description 11
- 239000004814 polyurethane Substances 0.000 claims abstract description 11
- 230000003287 optical effect Effects 0.000 claims description 27
- 239000012790 adhesive layer Substances 0.000 claims description 14
- 230000001681 protective effect Effects 0.000 claims description 14
- 125000000962 organic group Chemical group 0.000 claims description 11
- 229920002857 polybutadiene Polymers 0.000 claims description 11
- 239000005062 Polybutadiene Substances 0.000 claims description 8
- 230000004888 barrier function Effects 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000012788 optical film Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229920001195 polyisoprene Polymers 0.000 claims description 5
- 229920002367 Polyisobutene Polymers 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 abstract description 6
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 description 48
- 230000000694 effects Effects 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 10
- 241001025261 Neoraja caerulea Species 0.000 description 9
- 238000001723 curing Methods 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 7
- 238000002834 transmittance Methods 0.000 description 7
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- ZMLPKJYZRQZLDA-UHFFFAOYSA-N 1-(2-phenylethenyl)-4-[4-(2-phenylethenyl)phenyl]benzene Chemical class C=1C=CC=CC=1C=CC(C=C1)=CC=C1C(C=C1)=CC=C1C=CC1=CC=CC=C1 ZMLPKJYZRQZLDA-UHFFFAOYSA-N 0.000 description 5
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical class OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 description 4
- YGUMVDWOQQJBGA-VAWYXSNFSA-N 5-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-[(e)-2-[4-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound C=1C=C(\C=C\C=2C(=CC(NC=3N=C(N=C(NC=4C=CC=CC=4)N=3)N3CCOCC3)=CC=2)S(O)(=O)=O)C(S(=O)(=O)O)=CC=1NC(N=C(N=1)N2CCOCC2)=NC=1NC1=CC=CC=C1 YGUMVDWOQQJBGA-VAWYXSNFSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000001186 cumulative effect Effects 0.000 description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 2
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000002918 oxazolines Chemical class 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
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- 238000005507 spraying Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- SITYOOWCYAYOKL-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-dodecoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 SITYOOWCYAYOKL-UHFFFAOYSA-N 0.000 description 1
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- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 1
- QJIVRICYWXNTKE-UHFFFAOYSA-N 4-(8-methylnonoxy)-4-oxobutanoic acid Chemical compound CC(C)CCCCCCCOC(=O)CCC(O)=O QJIVRICYWXNTKE-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- RVWADWOERKNWRY-UHFFFAOYSA-N [2-(dimethylamino)phenyl]-phenylmethanone Chemical compound CN(C)C1=CC=CC=C1C(=O)C1=CC=CC=C1 RVWADWOERKNWRY-UHFFFAOYSA-N 0.000 description 1
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- 230000000996 additive effect Effects 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
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- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
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Images
Classifications
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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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
-
- 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
- C08K5/17—Amines; Quaternary ammonium compounds
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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
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
- C08K5/353—Five-membered rings
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C09J157/00—Adhesives based on unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
- C09J171/02—Polyalkylene oxides
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- C09J201/00—Adhesives based on unspecified macromolecular compounds
- C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09J201/06—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
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- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
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Abstract
The invention provides an ultravioletcuring resin composition with excellent transparency and a laminated body using the same. The ultravioletcuring resin composition comprises: (A) at least 1 polymer (B) modified with (meth) acrylate and selected from the group consisting of hydrocarbon polymers, polyoxyalkylene, and polyurethane, (C) a photopolymerization initiator, and a naphthalimide compound having a naphthalimide skeleton and/or a compound having a benzo group
Benzo of oxazoline skeleton
An oxazoline compound, and (D)1 a (meth) acryloyloxy group-containing monomer having at least 1 (meth) acryloyloxy group in a molecule and/or a plasticizer; the naphthalimide compound and/or the benzo (a) imide compound are/is added to the total 100 parts by mass of the polymer, the photopolymerization initiator, the (meth) acryloyloxy group-containing monomer and/or the plasticizer
Description
Technical Field
The present invention relates to an ultraviolet-curable resin composition and a laminate using the same.
Background
Conventionally, it has been proposed to bond functional films and the like constituting electronic device modules for displays such as touch panels with a photo-curable bonding composition (for example, patent document 1).
Background of the invention
Patent document
[ patent document 1 ] Japanese patent laid-open No. 2012-46658
Disclosure of Invention
Problems to be solved by the invention
When a hard coating material capable of exhibiting a blue light resistance function is coated on the surface or the back surface of the functional film, if a layer having a blue light resistance function and an adhesive layer are provided on the functional film, respectively, productivity is poor. Further, the inventors have found that if the adhesive layer is made to have a function of resisting blue light, the transparency becomes low.
The present invention has been made in view of the above problems, and an object thereof is to provide an ultravioletcuring resin composition having excellent transparency and a laminate using the same.
Technical scheme
In order to solve the above problems, the present inventors have made extensive studies and have found that the above problems can be solved by the following constitution.
1. An ultravioletcuring resin composition comprising: (A) at least 1 polymer selected from the group consisting of hydrocarbon polymers, polyoxyalkylene, and polyurethane, modified with (meth) acrylate,
(B) a photopolymerization initiator,
(C) naphthalimide compound having naphthalimide skeleton and/or benzene
Benzo of oxazoline skeleton
Oxazoline compounds, and
(D)1 a (meth) acryloyloxy group-containing monomer having at least 1 (meth) acryloyloxy group in the molecule and/or a plasticizer,
the naphthalimide compound and/or the benzo group based on 100 parts by mass of the total of the polymer, the photopolymerization initiator and the (meth) acryloyloxy group-containing monomer and/or the plasticizer
The amount of the oxazoline compound is 0.001 to 5 parts by mass.
2. The ultravioletcuring resin composition as described in the above 1, wherein the (meth) acrylate-modified hydrocarbon polymer has at least 1 hydrocarbon polymer selected from the group consisting of polyisobutylene, polyolefin, polyisoprene, polybutadiene and hydrogenated polybutadiene as a main chain, and has a (meth) acryloyloxy group or a group having a (meth) acryloyloxy group at a terminal and/or a side chain.
3. The ultravioletcuring resin composition as described in 1 or 2, wherein the (meth) acrylate-modified polyoxyalkylene group has a polyoxypropylene group as a main chain, and a group having a (meth) acryloyloxy group or a (meth) acryloyloxy group at a terminal and/or a side chain.
4. The ultravioletcuring resin composition according to any one of the above 1 to 3, wherein the weight average molecular weight of the polymer is 1,000 to 100,000.
5. The ultravioletcuring resin composition as set forth in any one of the above 1 to 4, wherein the naphthalimide compound is a compound represented by the following formula (1).
6. The ultravioletcuring resin composition as described in any one of 1 to 5, which is used for bonding an optical display panel to a touch panel, bonding an optical display panel to a protective panel, bonding a touch panel to a protective panel, bonding an optical display panel to an optical display panel, or bonding an optical film to a parallax barrier.
7. A laminate obtained by bonding an optical display panel and a touch panel, an optical display panel and a protective panel, a touch panel and a protective panel, an optical display panel and an optical display panel, or an optical film and a parallax barrier, using an adhesive layer formed from the ultraviolet curable resin composition according to any one of the above items 1 to 6.
Effects of the invention
The ultravioletcuring resin composition and the laminate of the present invention have excellent transparency.
Drawings
FIG. 1 is a schematic sectional view showing an example of a laminate of the present invention.
Detailed Description
[ ultravioletcuring resin composition ]
The present invention will be described in detail below.
First, the ultravioletcuring resin composition of the present invention will be explained below.
The ultravioletcuring resin composition of the present invention (the composition of the present invention) contains
(A) At least 1 polymer modified with (meth) acrylate and selected from the group consisting of hydrocarbon polymers, polyoxyalkylene, and polyurethane,
(B) a photopolymerization initiator,
(C) naphthalimide compound having naphthalimide skeleton, and
(D)1 a (meth) acryloyloxy group-containing monomer having at least 1 (meth) acryloyloxy group in the molecule and/or a plasticizer,
the amount of the naphthalimide-based compound is 0.001 to 5 parts by mass relative to 100 parts by mass of the total of the polymer, the photopolymerization initiator, and the (meth) acryloyloxy group-containing monomer and/or the plasticizer.
In the present specification, the polymer (a) may be referred to as a polymer, a component (a) or a component (a). (B) The same as the components described in (E) above.
Further, excellent transparency may be referred to as excellent effect of the present invention.
< (A) Polymer
The polymer (A) will be described below.
(A) The polymer is at least 1 selected from the group consisting of hydrocarbon polymers, polyoxyalkylene, and polyurethane, which are modified with (meth) acrylate.
(A) The polymer is not particularly limited as long as it has a (meth) acrylate modified group and at least 1 selected from the group consisting of hydrocarbon polymers, polyoxyalkylene groups, and polyurethanes as a main chain.
The (meth) acrylate-modified group may include, as one of preferable embodiments thereof, (meth) acryloyloxy group and a group having a (meth) acryloyloxy group.
In addition, "(meth) acryloyloxy" shall mean acryloyloxy (CH)2CHCOO-) or methacryloxy (CH)2＝C(CH3) COO-), "(meth) acrylate" shall mean acrylate or methacrylate.
(A) The number of (meth) acrylate-modified groups contained in 1 molecule of the polymer is 1 or more. The number of (meth) acrylate modifying groups is preferably 2 to 8, more preferably 2 to 4 per 1 molecule of the (a) polymer, from the viewpoint of more excellent effects of the present invention and excellent blue rotation resistance, appearance at the time of curing, and adhesion properties.
The (meth) acrylate-modifying group may be bonded to a terminal of the main chain and/or a side chain directly or through an organic group. The organic group is not particularly limited. The organic group may also have a urethane bond, for example.
From the viewpoint that the effect of the present invention is more excellent and the blue rotation resistance, appearance at the time of hardening, and adhesion property are excellent, the weight average molecular weight of the (a) polymer is preferably 1,000 to 100,000, more preferably 5,000 to 50,000. In the present invention, the weight average molecular weight is a value obtained in terms of standard polystyrene by a Gel Permeation Chromatograph (GPC) using Tetrahydrofuran (THF) as a solvent.
In view of the fact that the present invention is more excellent in the effect and excellent in the blue-ray resistance, appearance at the time of hardening and adhesion property, the (meth) acrylate-modified hydrocarbon polymer preferably has at least 1 hydrocarbon polymer selected from the group consisting of polyisobutylenes, polyolefins, polyisoprenes, polybutadienes and hydrogenated polybutadienes as a main chain.
The (meth) acrylate-modified polyoxyalkylene group has a polyoxyalkylene skeleton as a main chain. In view of the fact that the effect of the present invention is more excellent and the blue-ray resistance, appearance at the time of curing and adhesion are excellent, the polyoxyalkylene modified with a (meth) acrylate preferably has a polyoxyethylene or polyoxypropylene group as a main chain.
The (meth) acrylate-modified polyurethane has a polyurethane skeleton as a main chain.
The production of the polymer (A) is not particularly limited. Examples thereof include conventionally known methods.
< (B) photopolymerization initiator
The photopolymerization initiator is explained below.
The photopolymerization initiator contained in the composition of the present invention is not particularly limited as long as it can polymerize an ethylenic functional group (for example, (meth) acryloyloxy group) by light.
Specific examples of the photopolymerization initiator include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, acetoin, butyrin, toluoyl, benzil, benzophenone, p-methoxybenzophenone, diethoxyacetophenone, α -dimethoxy- α -phenylacetophenone, methylphenylacetic acid, ethylphenylglyoxylic acid, 4' -bis (dimethylaminobenzophenone), 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 2-dimethoxy-1, 2-diphenylethane-1-one, 1-hydroxycyclohexylphenylketone, and other carbonyl compounds, tetramethylthiuram monosulfide, tetramethylthiuram disulfide, and other sulfur compounds, azobisisobutyronitrile, azo-2, 4-dimethylvaleronitrile, and other azo compounds, and benzoyl peroxide, dibutyl peroxide, and other peroxide compounds.
Among them, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, and 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propan-1-one are preferable from the viewpoints of light stability, photocleavage efficiency, surface curability, compatibility, low volatility, and low odor.
The photopolymerization initiators may be used singly or in combination of two or more.
The amount of the photopolymerization initiator is preferably 1 to 10 parts by mass relative to 100 parts by mass of the (a) polymer.
< (C) naphthalimide compound and/or benzo
Oxazoline compound
(Naphthylimide compound)
The naphthalimide compound will be described below.
The naphthalimide compound contained in the composition of the present invention is a compound having a naphthalimide skeleton.
The composition of the present invention contains a naphthalimide compound, and therefore has excellent blue-light resistance.
In view of the more excellent effect of the present invention and the excellent viewpoint of having a high blue light resistance ratio, the naphthalimide-based compound is preferably a compound represented by the following formula (1).
Chemical formula 1
(in the formula (1), R1Represents a hydrogen atom or a hydrocarbon group which may have a hetero atom, R2Represents a hydrogen atom or an organic group, a plurality of R2May be respectively the same or different. )
R in the above formula (1)1Examples of the hydrocarbon group which may have a hetero atom include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a combination thereof. The hydrocarbon group may have an unsaturated bond.
Further, as R1The hydrocarbon group is preferably a linear or branched alkyl group, and the number of carbon atoms is preferably 1 to 12.
R in the above formula (1)2Examples of the organic group include functional groups such as an amine group and a hydroxyl group; a hydrocarbon group such as an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, or an aromatic hydrocarbon group; hydrocarbon groups, combinations thereof, and the like. In addition, the hydrocarbon group may have a hetero atom or an unsaturated bond.
Further, as R2The hydrocarbon group in the organic group is preferably an alkoxy group, and more preferably a methoxy group or an ethoxy group.
The naphthalimide compound can reduce the transmittance of at least part of light in the wavelength range of 385-495 nm.
As a commercially available product of such a naphthalimide compound, Lumogen F Violet 570 (manufactured by BASF) can be suitably exemplified.
(benzo
Oxazoline compounds
The following is a description of benzo
An oxazoline compound.
Benzo compounds contained in the compositions of the invention
The oxazoline compounds are substituted benzene
Compounds of the oxazoline skeleton.
The composition of the invention contains benzene
The oxazoline compound has excellent blue rotation resistance.
Having a benzene ring
The compound having an oxazoline skeleton being a compound having a benzo group
The compound of the azole ring is not particularly limited, but is preferably a compound represented by the following formula (I), and more preferably a compound represented by the following formula (Ia) among them, from the viewpoint that the overall blue-resistant optical rotation performance is more excellent.
Chemical formula 2
(in the formula (I), RaRepresents a hydrogen atom or an organic group, a plurality of RaMay be respectively the same or different. )
As R in the above formula (I)aExamples of the organic group include hydrocarbon groups which may have hetero atoms, specifically, aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and combinations thereof, and may have an unsaturated bond.
Furthermore, RaThe hydrocarbon group is preferably a linear or branched alkyl group, and more preferably a branched alkyl group.
Furthermore, RaThe number of carbon atoms of the hydrocarbon group represented is preferably 1 to 12, more preferably 3 to 6.
As such benzeneAnd are
Examples of commercially available products of oxazoline compounds include Tinopal OBCO (manufactured by BASF Co., Ltd.) and Nikkafluor OB (manufactured by Nikkafur Co., Ltd.).
The amount of the naphthoimide compound and/or the benzo (meth) acryloyl group-containing monomer and/or the plasticizer is 100 parts by mass based on 100 parts by mass of the total amount of the (a) polymer, the (B) photopolymerization initiator, the (meth) acryloyloxy group-containing monomer and/or the plasticizer (when the (meth) acryloyloxy group-containing monomer and the plasticizer are used in combination, the total amount of the (a) polymer, the (B) photopolymerization initiator, the (meth) acryloyloxy group-containing monomer and the plasticizer are the same as below)
The amount of the oxazoline compound is 0.001 to 5 parts by mass, preferably 0.001 to 2.0 parts by mass, more preferably 0.001 to 0.5 parts by mass, from the viewpoint that the effect of the present invention is more excellent.
(perylene Compounds)
The composition of the present invention may further contain a compound having a perylene skeleton (perylene compound). The compound having a perylene skeleton is not particularly limited. The perylene skeleton may also have substituents. The perylene skeleton is represented by the following formula (2).
Chemical formula 3
Examples of commercially available compounds having a perylene skeleton include Lumogen F Yellow 083 (manufactured by BASF).
The compound having a perylene skeleton can absorb a region (420 to 495nm) of a long wavelength end in blue light, compared with a compound having a naphthalimide skeleton.
(benzotriazole-based Compound)
The composition of the present invention may further contain a compound having a benzotriazole skeleton (benzotriazole-based compound). The compound having a benzotriazole skeleton is not particularly limited. The benzotriazole skeleton may also have a substituent. The benzotriazole skeleton is represented by the following formula (3).
Chemical formula 4
(in the formula (3), R3Represents a hydrogen atom or a hydrocarbon group which may have a hetero atom. )
R in the above formula (3)3Examples of the hydrocarbon group which may have a hetero atom include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a combination thereof, and may have an unsaturated bond.
Further, as R3The hydrocarbon group is preferably a linear or branched alkyl group, and the number of carbon atoms is preferably 1 to 12.
Examples of commercially available products of such a compound having a benzotriazole skeleton include Tinuvin Carboprotect (manufactured by BASF Co., Ltd.), Tinuvin 384-2 (manufactured by BASF Co., Ltd.), and the like.
The compound having a benzotriazole skeleton can absorb light having a wavelength of 220 to 430 nm.
(distyrylbiphenyl derivatives)
The compositions of the present invention may further comprise distyrylbiphenyl derivatives as fluorescent whitening agents. The distyrylbiphenyl derivative is a derivative of a compound in which 2 styryl groups are bonded to biphenyl, and specific examples thereof include a compound represented by the following formula (ii). The compound represented by the following formula (ii) is available as Tinopal NFWLIQ (BASF).
Chemical formula 5
(Hydroxyphenyltriazines)
The composition of the present invention may further contain a compound having a hydroxyphenyltriazine skeleton (hydroxyphenyltriazine-based compound) as an ultraviolet absorber. The hydroxyphenyl triazine compound is not particularly limited as long as it has a hydroxyphenyl group and a triazine ring bonded to each other by a single bond.
Examples of commercially available products of the hydroxyphenyltriazine compound include Tinuvin 400 (manufactured by BASF), Tinuvin 405 (manufactured by BASF), Tinuvin 460 (manufactured by BASF), Tinuvin 477 (manufactured by BASF), and Tinuvin 479 (manufactured by BASF).
The amounts of the perylene compound, the benzotriazole compound, the distyrylbiphenyl derivative, and the hydroxyphenyltriazine compound are not particularly limited, and are, for example, 0.001 to 5 parts by mass, preferably 0.001 to 2.0 parts by mass, and more preferably 0.001 to 0.5 parts by mass, based on 100 parts by mass of the total of the (a) polymer, (B) the photopolymerization initiator, and (D) the (meth) acryloyloxy group-containing monomer and/or the plasticizer.
< (D) A (meth) acryloyloxy group-containing monomer and/or plasticizer
(containing a (meth) acryloyloxy monomer)
The (meth) acryloyloxy group-containing monomer is described below.
The (meth) acryloyloxy group-containing monomer that may be contained in the composition of the present invention is not particularly limited as long as it is a monomer having at least 1 (meth) acryloyloxy group in 1 molecule.
The (meth) acryloyloxy group may be bonded to an organic group. The organic group is not particularly limited. Examples thereof include hydrocarbon groups which may contain hetero atoms such as oxygen atom, nitrogen atom, and sulfur atom. Examples of the hydrocarbon group include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a combination thereof. At least 1 of the carbon atoms or hydrogen atoms of the hydrocarbon group may be substituted with a substituent.
Examples of the substituent include a 1-valent substituent such as a hydroxyl group, an amino group, a mercapto group, or a halogen group; and 2-valent substituents such as ether bond, imine bond, thioether bond, polythioether bond, urethane bond, urea bond, ester bond, and amide bond.
Examples of the (meth) acryloyloxy group-containing monomer include (meth) acrylate esters of polyhydric alcohols.
Examples of the (meth) acrylate of the polyol include 2-functional compounds such as neopentyl glycol diacrylate; 3-functional compounds such as trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol tri (meth) acrylate, and the like; 4-functional compounds such as pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, and tripentaerythritol tetra (meth) acrylate; and 5-or more functional compounds such as dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol penta (meth) acrylate, tripentaerythritol hexa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, and tripentaerythritol octa (meth) acrylate.
Among them, from the viewpoint of further improving the effect of the present invention and further improving the blue-ray resistance, curability and adhesion, the 2-functional compound and the 3-functional compound are preferable, and neopentyl glycol diacrylate is more preferable.
The (meth) acryloyloxy group-containing monomers may be used singly or in combination of two or more.
From the viewpoint of more excellent effects of the present invention and excellent blue-ray resistance, curability, and viscosity, the amount of the (meth) acryloyloxy group-containing monomer is preferably 10 to 60 parts by mass, more preferably 10 to 50 parts by mass, relative to 100 parts by mass of the (a) polymer.
(plasticizer)
Hereinafter, the plasticizer will be described.
The plasticizer which the composition of the present invention may contain is not particularly limited.
Examples thereof include phthalic acid esters such as diisononyl phthalate (DINP), dioctyl phthalate, dibutyl phthalate and butylbenzyl phthalate, aliphatic dibasic acid esters such as dioctyl adipate, isodecyl succinate and dibutyl sebacate, alcohol esters such as diethylene glycol dibenzoate and pentaerythritol ester, aliphatic esters such as butyl oleate and methyl acetylricinoleate, phosphoric acid esters such as tricresyl phosphate, trioctyl phosphate and octyldiphenyl phosphate, propylene glycol adipate, butylene glycol adipate, epoxy plasticizers such as epoxidized soybean oil, epoxidized linseed oil and epoxy stearate, polyesters, polyethers such as polypropylene glycol and derivatives thereof, polystyrenes such as poly- α -methylstyrene and polystyrene, polybutadienes, butadiene-acrylonitrile copolymers, polychloroprenes, polyisoprenes and polybutenes, and paraffin oils, naphthene oils and aromatic oils.
Among them, dioctyl phthalate and liquid polybutadiene are preferable from the viewpoint of further excellent effects of the present invention, and excellent blue rotation resistance, solubility in other components, viscosity, and adhesiveness.
The plasticizers may be used alone or in combination of two or more.
From the viewpoint of more excellent effects of the present invention and excellent blue-ray resistance, curability, and viscosity, the amount of the plasticizer is preferably 10 to 60 parts by mass, more preferably 10 to 50 parts by mass, relative to 100 parts by mass of the (a) polymer.
In the present invention, when the (meth) acryloyloxy group-containing monomer and the plasticizer are used in combination, the total amount of both is preferably 10 to 60 parts by mass, more preferably 10 to 50 parts by mass, per 100 parts by mass of the (a) polymer, from the viewpoint of further excellent effects of the present invention, and excellent blue-ray resistance, curability, and viscosity.
< (E) epoxy polymer, fluorine polymer, or silicone
In view of the fact that the present invention is more excellent in the effect, and the blue-ray resistance and adhesion are excellent, the composition of the present invention preferably further contains (E) at least 1 selected from the group consisting of epoxy polymers, fluorine polymers, silicones, and modified substances thereof.
The epoxy polymer is not particularly limited as long as it is a polymer having 1 or more epoxy groups in 1 molecule.
The fluorine-based polymer is not particularly limited as long as it is a polymer having 1 or more fluorine atoms in 1 molecule.
The silicone is not particularly limited as long as it is a polymer having a polysiloxane in the main chain.
From the viewpoint that the effect of the present invention is more excellent and the blue rotation resistance and the adhesiveness are excellent, the weight average molecular weight of (E) is preferably 1,000 to 100,000, more preferably 5,000 to 50,000.
From the viewpoint of more excellent effects of the present invention and excellent blue-ray resistance and adhesion, the amount of (E) (the total amount of 2 or more species used) is preferably 0.1 to 3 parts by mass, more preferably 0.1 to 1 part by mass, based on 100 parts by mass of the total of (a) the polymer, (B) the photopolymerization initiator, (D) the (meth) acryloyloxy group-containing monomer and/or the plasticizer.
< other additives >
The composition of the present invention may further contain an additive within a range not impairing the object of the present invention. Examples of the additives include blue light absorbers other than (C), monomers other than (meth) acryloyloxy group-containing monomers, ultraviolet absorbers, fillers, antioxidants, antistatic agents, flame retardants, tackifiers, dispersants, antioxidants, antifoaming agents, leveling agents, matting agents, light stabilizers, dyes, and pigments.
< manufacturing method >
The production of the composition of the present invention is not particularly limited. For example, the above-mentioned (A) to (D), and if necessary, (E) and additives may be uniformly mixed to produce the composition of the present invention.
< uses et al >
The composition can form a 1-layer coating film which has the blue light resisting function and is transparent. In addition, the composition of the present invention can form a coating film having adhesion.
The compositions of the invention can be used, for example, as: a composition for forming a coating film having a blue light-blocking function, a composition for forming an adhesive layer, a plastic surface protective agent, a hard coat paint, a hard coat agent, an ultraviolet-curable paint, a primer composition, and the like.
The member to which the composition of the present invention can be applied is not particularly limited. Examples of the optical display panel, touch panel, protective panel, optical film, and parallax barrier are given. The above-mentioned members are not particularly limited. Examples of the member include conventionally known members.
The material of the member to which the composition of the present invention can be applied is not particularly limited. Examples thereof include plastics, rubbers, glasses, metals, and ceramics. The member may be in the form of a film, for example.
The plastic material that can be used in the composition of the present invention may be any of thermosetting resins and thermoplastic resins. Examples of the plastic include hard-to-adhere resins such as polyethylene terephthalate (PET), cyclic olefin polymers (including homopolymers, copolymers, and hydrogen additives), polymethyl methacrylate resin (PMMA resin), polycarbonate resin, polystyrene resin, acrylonitrile-styrene copolymer resin, polyvinyl chloride resin, acetic acid resin, ABS resin, polyester resin, and polyamide resin.
The member may also be subjected to a surface treatment such as corona treatment.
The method (method of use) of applying the composition of the present invention to a member is not particularly limited, and for example, a known coating method such as brush coating, flow coating, dip coating, spray coating, and spin coating can be used.
The curing method of the composition of the present invention includes a curing method using ultraviolet rays. When the composition of the present invention is cured by ultraviolet irradiation, the amount of ultraviolet irradiation (cumulative amount of light) used for curing the composition of the present invention is preferably 50 to 3,000mJ/cm from the viewpoints of rapid curing properties and workability2. The means for irradiating ultraviolet rays is not particularly limited. Examples thereof include conventionally known devices. When hardening, heating may be used in combination.
The composition of the present invention is useful for, for example, bonding an optical display panel to a touch panel, bonding an optical display panel to a protective panel, bonding a touch panel to a protective panel, bonding an optical display panel to an optical display panel, or bonding an optical film to a parallax barrier.
[ laminate ]
The laminate of the present invention will be described below.
The laminate of the present invention is
The present invention provides a method for producing a multilayer structure comprising bonding an optical display panel and a touch panel, an optical display panel and a protective panel, a touch panel and a protective panel, an optical display panel and an optical display panel, or an optical film and a parallax barrier, by using an adhesive layer formed from the ultravioletcuring resin composition.
The laminate of the present invention has an adhesive layer formed using the composition of the present invention, and therefore has excellent at least one of blue-ray resistance and transparency.
The composition used in the laminate of the present invention is not particularly limited as long as it is the composition of the present invention.
The member used in the laminate of the present invention is not particularly limited, and the optical display panel, touch panel, protective panel, optical film, and parallax barrier are not particularly limited. Examples of the member include conventionally known members.
The structure of the laminate of the present invention will be described below with reference to the drawings. However, the present invention is not limited to the drawings.
FIG. 1 is a schematic sectional view showing an example of a laminate of the present invention.
In FIG. 1, a laminate 100 includes a member 102 as a 1 st member, a member 106 as a 2 nd member, and an adhesive layer 104 formed using the composition of the present invention. The member 102 and the member 106 are joined by an adhesive layer 104.
The thicknesses of the member and the adhesive layer are not particularly limited. The thickness of each member is preferably about 50 to 300 μm. The thickness of the adhesive layer is preferably about 0.05 to 2,000 μm.
< manufacturing method >
The method for producing the laminate of the present invention includes, for example, a method including the following steps: the composition of the present invention was applied to the 1 st member and dried, and then the 2 nd member was stacked and irradiated with ultraviolet rays.
The method of applying the composition of the present invention is not particularly limited, and known coating methods such as brush coating, flow coating, dip coating, spray coating, and spin coating can be used.
Further, the temperature for drying after coating is preferably 20 ℃ to 110 ℃.
In addition, consideration is given to the rapid hardeningFrom the viewpoint of workability, the amount of ultraviolet irradiation (cumulative amount of light) used for curing the composition of the present invention is preferably 50 to 3,000mJ/cm2. The means for irradiating ultraviolet rays is not particularly limited. Examples thereof include conventionally known devices. When hardening, heating may be used in combination.
Examples
The present invention will be described in detail below with reference to examples. The invention is not limited to such embodiments.
< production of composition >
The components shown in table 1 below were mixed by a mixer in the composition (parts by mass) shown in the table to prepare a composition.
< evaluation of engagement magnitude >
A test piece for measuring a bonding level value was prepared in the following manner.
First, each of the compositions prepared as described above was applied to a circular glass having a diameter of 5mm, the glass was bonded to another glass in a cross shape to a bonding thickness of 0.3mm, and then UV-cured. The UV irradiation condition is illuminance of 300mW/cm2The cumulative light quantity was 300mJ/cm2The UV irradiation device is a high-pressure mercury lamp.
The engagement magnitude was determined in the following manner. One of the glass pieces joined in a cross shape was fixed, and the other glass piece was stretched at a stretching speed of 5mm/min, and the maximum value at which the glass pieces joined in a cross shape were peeled was measured as a joining amount value. The results are shown in Table 1.
< production of laminate >
Each of the compositions thus prepared was applied to a polyethylene terephthalate film (PET texture: trade name: A-4300, manufactured by Toyo Boseki Co., Ltd., thickness: 125 μm) using a coating bar, dried at 80 ℃ for 1 minute, and irradiated with Ultraviolet (UV) light using a GS UV SYSTEM manufactured by Chuangkou Spring Co., Ltd. (UV irradiation condition: illuminance 300 mW/cm)2The cumulative light quantity was 300mJ/cm2A high-pressure mercury lamp as a UV irradiation device), and curing the composition to form an adhesive layer, thereby obtaining a laminate. The thickness of the adhesive layer was 0.1. mu.m.
< evaluation of average blue light resistance ratio, Total light transmittance, haze >
Using the laminate produced as described above, the following evaluations were carried out. The results are shown in Table 1.
(average anti-blue light ratio)
The laminate thus prepared was irradiated with light having a wavelength in the range of 800 to 300nm using a Hitachi spectrophotometer 3900H as an apparatus, and the average transmittance (%) in the range of 385 to 495nm was measured. The measurement results were substituted into the following formula to calculate the average blue light resistance ratio of the laminate. Average ratio (%) of blue light resistance of the adhesive layer of 100- (average transmittance in the range of 385 to 495nm)
(all light transmittance)
The total light transmittance of the laminate thus obtained was measured according to JIS K7361 using a haze meter (HM-150, manufactured by muraea color technology research). And the results are shown as the average of the number of samples n-3.
The total light transmittance is preferably 90% or more.
(haze)
The haze of the laminate thus obtained was measured according to JIS K7105 using a haze meter (HM-150, manufactured by color technical research in village). And the results are shown as the average of the number of samples n-3.
In the present invention, when the haze is 1.0% or less, the transparency is excellent.
TABLE 2
The mixtures 1 to 4 shown in Table 1 are specifically as follows.
The components in table 2 were used as mixtures 1 to 4 in the composition (parts by mass) shown in the table.
TABLE 3
The ingredients shown in Table 2 are specifically as follows.
(meth) acrylate-modified polyisoprene: the trade name is UC-1 manufactured by Kuraray. The weight average molecular weight was 25,000, and 3 (meth) acrylate groups per 1 molecule.
(meth) acrylate-modified polyurethane: trade name is UA-1 manufactured by Light Chemical company. The weight average molecular weight was 2,400, having 2 (meth) acrylate groups per 1 molecule.
(meth) acrylate-modified polybutadiene: trade name is TE-2000, manufactured by Nippon Caoda corporation. The weight average molecular weight was 2,000, and 2 (meth) acrylate groups per 1 molecule.
(meth) acrylate-modified hydrogenated polybutadiene: the trade name is TEAI-1000 manufactured by Nippon Caoda. The weight average molecular weight was 1,000, and 2 (meth) acrylate groups per 1 molecule.
(meth) acrylate-modified polypropylene glycol: polyoxypropylene modified with (meth) acrylate, trade name FA-P270A, manufactured by Hitachi chemical Co. The weight average molecular weight 823 has 2 (meth) acrylate groups per 1 molecule.
Photopolymerization initiator: irgacure 184 (manufactured by BASF corporation).
A (meth) acryloyloxy group-containing monomer 1: trimethylolpropane triacrylate, product name TMPTA, manufactured by DaicelAllnex Co.
A (meth) acryloyloxy group-containing monomer 2: neopentyl glycol diacrylate, trade name FA-125M, manufactured by Hitachi chemical Co., Ltd.
Plasticizer 1: liquid polybutadiene, trade name L-LIR, manufactured by Kuraray Co.
The components other than the mixtures 1 to 4 shown in Table 1 are specifically as follows.
Naphthalimide compound 1: lumogen F Violet 570(BASF corporation).
Benzene and toluene
Oxazoline compound 1: tinopal OBCO (manufactured by BASF).
Perylene compound 1: lumogen F Yellow 083 (product of BASF corporation).
Benzotriazole compound 1: tinuvin Carboprotect (manufactured by BASF corporation).
Distyrylbiphenyl derivative 1: tinopal NFW LIQ (manufactured by BASF).
Hydroxyphenyl triazine compound 1: tinuvin 479 (manufactured by BASF).
As is clear from the results shown in Table 1, comparative examples 1 to 3 in which the amount of the naphthalimide-based compound exceeds a predetermined amount have high haze and low transparency.
On the other hand, examples 1 to 16 are excellent in transparency. In addition, examples 1 to 16 have high bonding values, excellent adhesion, and high blue rotation resistance.
Further, when example 5 and example 8 are compared, it is found that example 8 containing the (meth) acrylate-modified polyurethane is more excellent in adhesion than example 5 containing no (meth) acrylate-modified polyurethane.
Claims (8)
1. An ultravioletcuring resin composition comprising: (A) at least 1 polymer modified with (meth) acrylate and selected from the group consisting of hydrocarbon polymers, polyoxyalkylene, and polyurethane,
(B) a photopolymerization initiator,
(C) naphthalimide compound having naphthalimide skeleton, and
(D)1 a (meth) acryloyloxy group-containing monomer having at least 1 (meth) acryloyloxy group in the molecule and/or a plasticizer,
the amount of the naphthalimide-based compound is 0.001 to 5 parts by mass relative to 100 parts by mass of the total of the polymer, the photopolymerization initiator, and the (meth) acryloyloxy group-containing monomer and/or the plasticizer.
2. The ultravioletcuring resin composition according to claim 1, wherein the (meth) acrylate-modified hydrocarbon polymer has a polyolefin as a main chain, and has a (meth) acryloyloxy group or a group having a (meth) acryloyloxy group at a terminal and/or a side chain.
3. The ultravioletcuring resin composition according to claim 1, wherein the (meth) acrylate-modified hydrocarbon polymer has at least 1 hydrocarbon polymer selected from the group consisting of polyisobutylene, polyisoprene, polybutadiene and hydrogenated polybutadiene as a main chain, and has a (meth) acryloyloxy group or a group having a (meth) acryloyloxy group at a terminal and/or a side chain.
4. The ultravioletcuring resin composition according to claim 1, wherein the (meth) acrylate-modified polyoxyalkylene group has a polyoxypropylene group as a main chain, and has a (meth) acryloyloxy group or a group having a (meth) acryloyloxy group at a terminal and/or a side chain.
5. The ultravioletcuring resin composition according to any one of claims 1 to 4, wherein the weight average molecular weight of the polymer is 1,000 to 100,000.
6. The ultravioletcuring resin composition according to any one of claims 1 to 4, wherein the naphthalimide compound is a compound represented by the following formula (1):
chemical formula 1
In the formula (1), R1Represents a hydrogen atom or a hydrocarbon group which may have a hetero atom, R2Represents a hydrogen atom or an organic group, a plurality of R2May be respectively the same or different.
7. The ultravioletcuring resin composition according to any one of claims 1 to 4, which is used for bonding an optical display panel to a touch panel, bonding an optical display panel to a protective panel, bonding a touch panel to a protective panel, bonding an optical display panel to an optical display panel, or bonding an optical film to a parallax barrier.
8. A laminate obtained by bonding an optical display panel and a touch panel, an optical display panel and a protective panel, a touch panel and a protective panel, an optical display panel and an optical display panel, or an optical film and a parallax barrier, by using an adhesive layer formed from the ultravioletcuring resin composition according to any one of claims 1 to 7.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014-164541 | 2014-08-12 | ||
| JP2014164541 | 2014-08-12 | ||
| PCT/JP2015/071976 WO2016024492A1 (en) | 2014-08-12 | 2015-08-03 | Ultraviolet-ray-curable resin composition and laminate using same |
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| Publication Number | Publication Date |
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| CN106574027A CN106574027A (en) | 2017-04-19 |
| CN106574027B true CN106574027B (en) | 2020-05-22 |
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| Country | Link |
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| JP (1) | JP6269839B2 (en) |
| KR (1) | KR101887430B1 (en) |
| CN (1) | CN106574027B (en) |
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| WO (1) | WO2016024492A1 (en) |
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| JP6643574B2 (en) * | 2016-02-16 | 2020-02-12 | 協立化学産業株式会社 | Photocurable resin composition |
| JP2018090683A (en) * | 2016-12-01 | 2018-06-14 | 旭硝子株式会社 | Curable composition, adhesive layer, adhesive layer-fitted face material, laminated body and image display device |
| WO2019004047A1 (en) * | 2017-06-27 | 2019-01-03 | 住友化学株式会社 | Adhesive composition and film with adhesive layer |
| WO2019016963A1 (en) * | 2017-07-21 | 2019-01-24 | 日本化薬株式会社 | Ultraviolet curable adhesive, and lamination method and article using same |
| CN116082989A (en) * | 2018-02-27 | 2023-05-09 | 积水化学工业株式会社 | Interlayer film for laminated glass and laminated glass |
| KR102024464B1 (en) * | 2018-03-19 | 2019-09-23 | 문승호 | Ultraviolet and blue light blocking aqueous emulsion composition and method of manufacturing the same |
| JP2020117586A (en) | 2019-01-22 | 2020-08-06 | 株式会社リコー | Curable composition, storage container, two-dimensional or three-dimensional image forming apparatus, two-dimensional or three-dimensional image forming method, and cured product |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS5850516A (en) * | 1981-09-22 | 1983-03-25 | Nippon Sheet Glass Co Ltd | Color developing display panel |
| JPS5854376A (en) * | 1981-09-28 | 1983-03-31 | 日本板硝子株式会社 | Color developing indication laminated panel |
| JPS6131449A (en) * | 1984-07-23 | 1986-02-13 | Nippon Kayaku Co Ltd | Ultraviolet-curing resin composition |
| DE112011102260T5 (en) * | 2010-07-02 | 2013-08-08 | Tokuyama Corp. | A photohardenable composition for embossing printing and a method of forming a pattern by means of the composition |
| JP5755419B2 (en) * | 2010-08-27 | 2015-07-29 | 協立化学産業株式会社 | Photo-curing adhesive composition for bonding optical display or touch sensor and optical display or touch sensor bonded using the same |
| JP5909078B2 (en) * | 2011-11-09 | 2016-04-26 | 日本化薬株式会社 | UV curable resin composition, cured product and article |
| JP5953319B2 (en) * | 2012-01-13 | 2016-07-20 | 日本化薬株式会社 | Optical member and ultraviolet curable adhesive used in the production thereof |
| JP2014025021A (en) * | 2012-07-30 | 2014-02-06 | Toyo Ink Sc Holdings Co Ltd | Photocurable colored adhesive |
| JP2014052538A (en) * | 2012-09-07 | 2014-03-20 | Nippon Shokubai Co Ltd | Photosetting resin composition for liquid crystal panel, method for curing the composition, and cured product |
| JP5459446B1 (en) * | 2013-04-30 | 2014-04-02 | 横浜ゴム株式会社 | Ultraviolet curable resin composition and laminate using the same |
| JP2015017205A (en) * | 2013-07-12 | 2015-01-29 | 日本化薬株式会社 | Photocurable colored composition, cured product and article |
| JP5651797B1 (en) * | 2014-06-30 | 2015-01-14 | 尾池工業株式会社 | A method for producing a hard coat transfer film, a hard coat transfer film, and a polymer resin plate or polymer resin film provided with a hard coat layer. |
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- 2015-08-03 JP JP2016542537A patent/JP6269839B2/en not_active Expired - Fee Related
- 2015-08-03 WO PCT/JP2015/071976 patent/WO2016024492A1/en active Application Filing
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| TWI665521B (en) | 2019-07-11 |
| KR20170023972A (en) | 2017-03-06 |
| KR101887430B1 (en) | 2018-08-10 |
| TW201612637A (en) | 2016-04-01 |
| WO2016024492A1 (en) | 2016-02-18 |
| JPWO2016024492A1 (en) | 2017-06-08 |
| CN106574027A (en) | 2017-04-19 |
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