JP2020158650A - Curable composition and cured product of the same - Google Patents
Curable composition and cured product of the same Download PDFInfo
- Publication number
- JP2020158650A JP2020158650A JP2019060238A JP2019060238A JP2020158650A JP 2020158650 A JP2020158650 A JP 2020158650A JP 2019060238 A JP2019060238 A JP 2019060238A JP 2019060238 A JP2019060238 A JP 2019060238A JP 2020158650 A JP2020158650 A JP 2020158650A
- Authority
- JP
- Japan
- Prior art keywords
- curable composition
- mass
- meth
- acrylate
- urethane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 68
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 34
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 34
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000003565 thiocarboxylic acid derivatives Chemical class 0.000 claims abstract description 18
- 239000003999 initiator Substances 0.000 claims abstract description 10
- 238000002834 transmittance Methods 0.000 abstract description 35
- 239000000758 substrate Substances 0.000 abstract description 15
- 238000000576 coating method Methods 0.000 description 30
- 239000011248 coating agent Substances 0.000 description 28
- 238000011156 evaluation Methods 0.000 description 25
- 239000000463 material Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 11
- -1 hydrocarbon polyols Chemical class 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 230000001588 bifunctional effect Effects 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- 238000001723 curing Methods 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- 238000007650 screen-printing Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 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
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 230000005540 biological transmission Effects 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
- 239000003085 diluting agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229940105570 ornex Drugs 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 2
- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 1
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-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
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- GIMQKKFOOYOQGB-UHFFFAOYSA-N 2,2-diethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)(OCC)C(=O)C1=CC=CC=C1 GIMQKKFOOYOQGB-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- UMLWXYJZDNNBTD-UHFFFAOYSA-N 2-(dimethylamino)-1-phenylethanone Chemical compound CN(C)CC(=O)C1=CC=CC=C1 UMLWXYJZDNNBTD-UHFFFAOYSA-N 0.000 description 1
- KJSGODDTWRXQRH-UHFFFAOYSA-N 2-(dimethylamino)ethyl benzoate Chemical compound CN(C)CCOC(=O)C1=CC=CC=C1 KJSGODDTWRXQRH-UHFFFAOYSA-N 0.000 description 1
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 1
- BXYWKXBAMJYTKP-UHFFFAOYSA-N 2-[2-[2-[2-(3-sulfanylpropanoyloxy)ethoxy]ethoxy]ethoxy]ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOCCOCCOCCOC(=O)CCS BXYWKXBAMJYTKP-UHFFFAOYSA-N 0.000 description 1
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- SUODCTNNAKSRHB-UHFFFAOYSA-N 2-ethylhexyl 3-sulfanylpropanoate Chemical compound CCCCC(CC)COC(=O)CCS SUODCTNNAKSRHB-UHFFFAOYSA-N 0.000 description 1
- 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
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- WXUKWXKGNXTMLW-UHFFFAOYSA-N 2-nitro-9h-fluorene;(phenyldisulfanyl)benzene Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1.C1=CC=C2C3=CC=C([N+](=O)[O-])C=C3CC2=C1 WXUKWXKGNXTMLW-UHFFFAOYSA-N 0.000 description 1
- UMWZLYTVXQBTTE-UHFFFAOYSA-N 2-pentylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CCCCC)=CC=C3C(=O)C2=C1 UMWZLYTVXQBTTE-UHFFFAOYSA-N 0.000 description 1
- SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 description 1
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- DITPLXUFWDEMDN-UHFFFAOYSA-N 4-methoxybutyl 3-sulfanylpropanoate Chemical compound COCCCCOC(=O)CCS DITPLXUFWDEMDN-UHFFFAOYSA-N 0.000 description 1
- BVEYJWQCMOVMAR-UHFFFAOYSA-N 5-Hydroxy-4-octanone Chemical compound CCCC(O)C(=O)CCC BVEYJWQCMOVMAR-UHFFFAOYSA-N 0.000 description 1
- ZRIMDWRLVGDUBW-UHFFFAOYSA-N 5-hydroxy-2-methylpent-2-enoic acid phosphoric acid Chemical compound P(=O)(O)(O)O.OCCC=C(C(=O)O)C ZRIMDWRLVGDUBW-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- IHANAAYEYHGCRT-UHFFFAOYSA-N OC(C(C(CCOC(CCS)=O)(CCOC(CCS)=O)CCOC(CCS)=O)S)=O Chemical class OC(C(C(CCOC(CCS)=O)(CCOC(CCS)=O)CCOC(CCS)=O)S)=O IHANAAYEYHGCRT-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- 230000009172 bursting Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- SSTAXLJQSRFHMB-UHFFFAOYSA-N ethyl 1,4-dimethylcyclohexa-2,4-diene-1-carboxylate Chemical compound CCOC(=O)C1(C)CC=C(C)C=C1 SSTAXLJQSRFHMB-UHFFFAOYSA-N 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- UCUPUEARJPTGKU-UHFFFAOYSA-N octadecyl 3-sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCS UCUPUEARJPTGKU-UHFFFAOYSA-N 0.000 description 1
- LWNSNYBMYBWJDN-UHFFFAOYSA-N octyl 3-sulfanylpropanoate Chemical compound CCCCCCCCOC(=O)CCS LWNSNYBMYBWJDN-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
本発明は、硬化性組成物、例えば透明のディスプレイや接着剤の製造に用いられる硬化性組成物、およびその硬化物に関する。 The present invention relates to curable compositions, such as curable compositions used in the manufacture of transparent displays and adhesives, and cured products thereof.
近年の画像形成技術の進歩により、液晶ディスプレイやタッチパネル等の電子機器における画像品質の向上が目覚ましい。このような高品質の画像の再現性を向上させるために、画像表示装置のスクリーン等についても品質の向上が望まれている。すなわち、画像表示装置で高画質の動画や静止画像を高精度で再現可能とするために、ディスプレイやその接着剤等が優れた透明性を有すること、すなわち無色透明であることが必須である。 Due to recent advances in image formation technology, the improvement in image quality in electronic devices such as liquid crystal displays and touch panels is remarkable. In order to improve the reproducibility of such a high-quality image, it is desired to improve the quality of the screen of the image display device and the like. That is, in order for the image display device to be able to reproduce high-quality moving images and still images with high accuracy, it is essential that the display and its adhesive have excellent transparency, that is, they are colorless and transparent.
このような要求に合致する高い透明性を有する樹脂の硬化物を得るために、光硬化成分と所定の無機粒子を用いた活性エネルギー線硬化性樹脂組成物が提案されている(特許文献1)。同文献では透明性の指標としてヘーズ(曇り度)を制御し、これにより優れた透明性の高い硬化性組成物が得られている。 In order to obtain a cured resin having high transparency that meets such requirements, an active energy ray-curable resin composition using a photocurable component and predetermined inorganic particles has been proposed (Patent Document 1). .. In the same document, haze (cloudiness) is controlled as an index of transparency, whereby an excellent curable composition having high transparency is obtained.
画像表示装置等のスクリーン等において用いられる硬化性組成物の透明硬化物は、さらに画像を明るく鮮明に視認可能とすべき要求が存在する。しかしながら、特許文献1に示されるような従来の樹脂組成物では、所定の透明性は得られているものの、光線透過率を検討しておらず、画像の鮮明な視認性が必ずしも十分とはいえない。
また、電子機器の製造にあっては、硬化性組成物が、電子機器の本体等(基板等)に対して良好に密着することが要求される。このような状況下、従来の樹脂組成物では、所定の使用条件の品質の維持や基板との密着性について未だ改良の余地がある。
The transparent cured product of the curable composition used in a screen or the like of an image display device has a demand for making an image brighter and clearer. However, in the conventional resin composition as shown in
Further, in the manufacture of an electronic device, it is required that the curable composition adheres well to the main body of the electronic device (such as a substrate). Under such circumstances, there is still room for improvement in the conventional resin composition in terms of maintaining the quality under predetermined usage conditions and adhering to the substrate.
本発明は、基板に対する密着性に優れるとともに、高い全光線透過率および良好に抑制された曇り度を有する硬化物を形成することが可能な硬化性組成物、およびその硬化物を提供することを目的とする。 The present invention provides a curable composition capable of forming a cured product having excellent adhesion to a substrate, high total light transmittance and well-suppressed cloudiness, and a cured product thereof. The purpose.
本発明者等は上記を鑑み、鋭意検討した結果、(A)ウレタン(メタ)アクリレート、(B)チオカルボン酸誘導体、(C)トリアリルイソシアヌレート、および(D)光重合開始剤、を含む硬化性組成物であって、(A)ウレタン(メタ)アクリレート100質量部に対して(B)チオカルボン酸誘導体を50質量部以上、(A)ウレタン(メタ)アクリレート100質量部に対して(C)トリアリルイソシアヌレートを40質量部以上含むことを特徴とする硬化性組成物により上記課題を解決しうることを見出し、本発明を完成するに至った。 As a result of diligent studies in view of the above, the present inventors have cured the mixture containing (A) urethane (meth) acrylate, (B) thiocarboxylic acid derivative, (C) triallyl isocyanurate, and (D) photopolymerization initiator. In the sex composition, 50 parts by mass or more of the (B) thiocarboxylic acid derivative with respect to 100 parts by mass of (A) urethane (meth) acrylate, and (C) with respect to 100 parts by mass of (A) urethane (meth) acrylate. We have found that the above-mentioned problems can be solved by a curable composition containing 40 parts by mass or more of triallyl isocyanurate, and have completed the present invention.
本発明の硬化性組成物では、(A)ウレタン(メタ)アクリレート、(B)チオカルボン酸誘導体、(C)トリアリルイソシアヌレートの合計質量が、硬化性組成物の全体の質量の95%以上であることが好ましい。 In the curable composition of the present invention, the total mass of (A) urethane (meth) acrylate, (B) thiocarboxylic acid derivative, and (C) triallyl isocyanurate is 95% or more of the total mass of the curable composition. It is preferable to have.
また、本発明の課題は、本発明の硬化性組成物から得られる透明硬化物により解決される。 Further, the problem of the present invention is solved by a transparent cured product obtained from the curable composition of the present invention.
本発明の硬化性組成物は、基板との密着性が高い。さらに本発明の硬化性組成物を硬化させることにより、曇り度が抑制され、且つ高い全光線透過率を有する透明性の高い硬化物を得ることができる。 The curable composition of the present invention has high adhesion to a substrate. Further, by curing the curable composition of the present invention, it is possible to obtain a highly transparent cured product having a high degree of cloudiness and a high total light transmittance.
本発明の硬化性組成物は、(A)ウレタン(メタ)アクリレート、 (B)チオカルボン酸誘導体、(C)トリアリルイソシアヌレート、および(D)光重合開始剤、を含む硬化性組成物であって、(A)ウレタン(メタ)アクリレート100質量部に対して(B)チオカルボン酸誘導体を40質量部以上、(A)ウレタン(メタ)アクリレート100質量部に対して(C)トリアリルイソシアヌレートを50質量部以上含むことを特徴とする。
本発明の硬化性組成物は基板に対する密着性に優れ、その硬化物は高い光線透過率とを有し、曇り度(ヘーズ)が抑制されているため、これにより優れた透明性および透過性を有する。
The curable composition of the present invention is a curable composition containing (A) urethane (meth) acrylate, (B) thiocarboxylic acid derivative, (C) triallyl isocyanurate, and (D) photopolymerization initiator. For 100 parts by mass of (A) urethane (meth) acrylate, 40 parts by mass or more of (B) thiocarboxylic acid derivative, and (C) triallyl isocyanurate with 100 parts by mass of (A) urethane (meth) acrylate. It is characterized by containing 50 parts by mass or more.
The curable composition of the present invention has excellent adhesion to a substrate, and the cured product has a high light transmittance and the haze is suppressed, thereby providing excellent transparency and transparency. Have.
本発明では透明性の指標としてヘーズ(Haze)を用いる。
ヘーズとは曇りの度合のことで、ガラス、プラスチックや液体などの透明材料の透明の程度を表わすものであり、試験片の散乱光線透過率を全光線透過率で割った値の100分率で表される。したがって、値が小さいほど、散乱光の透過が少なく、材料に曇りがないことを意味する。
また、本発明では、透過性の指標として透過率(全光線透過率)を用いる。透過率とは、測定対象となる材料に入射する光量に対する透過光量の割合であり、材料表面における反射や材料内部における吸収も考慮した値として得られる。
本発明において、ヘーズはJIS−K−7361:2000に準拠して測定し、「透明」ないし「透明性が高い」とはヘーズが5%未満であることを意味する。好ましくはヘーズが1%未満である。
更に、本発明において、全光線透過率はJIS K7361-1の方法により測定し、透過率が高い(透過性に優れる)とは、透過率が99.0%以上であることを意味する。
以下、各成分について詳述する。
In the present invention, Haze is used as an index of transparency.
Haze is the degree of cloudiness, which indicates the degree of transparency of transparent materials such as glass, plastic, and liquid. It is a percentage of the value obtained by dividing the scattered light transmittance of the test piece by the total light transmittance. expressed. Therefore, the smaller the value, the less the scattered light is transmitted and the less cloudy the material is.
Further, in the present invention, the transmittance (total light transmittance) is used as an index of transmittance. The transmittance is a ratio of the amount of transmitted light to the amount of light incident on the material to be measured, and is obtained as a value in consideration of reflection on the surface of the material and absorption inside the material.
In the present invention, the haze is measured according to JIS-K-7361: 2000, and "transparent" or "highly transparent" means that the haze is less than 5%. The haze is preferably less than 1%.
Further, in the present invention, the total light transmittance is measured by the method of JIS K7361-1, and high transmittance (excellent in transmittance) means that the transmittance is 99.0% or more.
Hereinafter, each component will be described in detail.
[(A)ウレタン(メタ)アクリレート]
本発明の硬化性組成物は(A)ウレタン(メタ)アクリレートを含む。
なお、本明細書において(メタ)アクリレートとは、アクリレート及びメタクリレートを総称する用語として用いられ、アクリレートもしくはメタクリレートのいずれか一方または双方を含む。他の類似の表現についても同様である。
ウレタン(メタ)アクリレート樹脂は、例えば、ポリオールとポリイソシアネートによりウレタンプレポリマーを合成し、そこに、水酸基を有する(メタ)アクリレートを付加させることにより製造することができる。
ポリオールとしては、例えば、炭化水素ポリオール、ポリエーテルポリオール、ポリエステルポリオール、ポリカーボネートポリオールなどの公知のポリオールを用いることができる。また、ポリイソシアネートとしては、例えば、芳香族ポリイソシアネート、脂肪族ポリイソシアネート、芳香族脂肪族ポリイソシアネート、脂環式ポリイソシアネートなどの公知のポリイソシアネートを用いることができる。
本発明の硬化性組成物は(A)ウレタン(メタ)アクリレートを含むことにより、硬化性組成物の基板に対する密着性が得られ、さらに硬化性組成物を硬化することにより得られる硬化塗膜の柔軟性が得られ、基板からの剥離の可能性が抑制される。(メタ)アクリロイル官能基数は、あまり大きいと架橋密度が高くなって硬化物の反りが大きくなり、強靱性も悪くなる傾向があることから、2官能、3官能のものが好ましい。
[(A) Urethane (meth) acrylate]
The curable composition of the present invention contains (A) urethane (meth) acrylate.
In addition, in this specification, (meth) acrylate is used as a generic term for acrylate and methacrylate, and includes either one or both of acrylate and methacrylate. The same is true for other similar expressions.
The urethane (meth) acrylate resin can be produced, for example, by synthesizing a urethane prepolymer with a polyol and a polyisocyanate and adding a (meth) acrylate having a hydroxyl group to the urethane prepolymer.
As the polyol, for example, known polyols such as hydrocarbon polyols, polyether polyols, polyester polyols, and polycarbonate polyols can be used. Further, as the polyisocyanate, for example, known polyisocyanates such as aromatic polyisocyanate, aliphatic polyisocyanate, aromatic aliphatic polyisocyanate, and alicyclic polyisocyanate can be used.
The curable composition of the present invention contains (A) urethane (meth) acrylate to obtain adhesion of the curable composition to the substrate, and further cures the curable composition to obtain a cured coating film. Flexibility is obtained and the possibility of peeling from the substrate is suppressed. If the number of (meth) acryloyl functional groups is too large, the crosslink density is high, the warpage of the cured product is large, and the toughness tends to be poor. Therefore, bifunctional and trifunctional ones are preferable.
本発明では、2個の(メタ)アクリロイル基を有するウレタン樹脂が特に好ましく使用される。 さらに、二官能ウレタン(メタ)アクリレートは、その重量平均分子量が、1500〜20000の範囲にあることが好ましい。二官能ウレタン(メタ)アクリレートの重量平均分子量が1500以上であることにより、二官能ウレタン(メタ)アクリレートの硬化収縮が低下し、硬化物の反りが生じにくい。一方、二官能ウレタン(メタ)アクリレートの重量平均分子量が20000以下とされることにより、粘度が良好とされて組成物調製における取り扱い性が向上する。 In the present invention, a urethane resin having two (meth) acryloyl groups is particularly preferably used. Further, the weight average molecular weight of the bifunctional urethane (meth) acrylate is preferably in the range of 1500 to 20000. When the weight average molecular weight of the bifunctional urethane (meth) acrylate is 1500 or more, the curing shrinkage of the bifunctional urethane (meth) acrylate is reduced, and the cured product is less likely to warp. On the other hand, when the weight average molecular weight of the bifunctional urethane (meth) acrylate is 20000 or less, the viscosity is improved and the handleability in the composition preparation is improved.
二官能ウレタン(メタ)アクリレートの市販品の例には、新中村化学工業製U−108A、U−200AX、UA−112P、UA−5201、U−340AX、UA−511、UA−512、UA−311、UA−412A、UA−4200、UA−4400、UA−340P、UA−2235PE、UA−160TM、UA−6100、U−108、UA−4000、UA−122P、UA−5201、UA−512、UA−W2、UA−7000、U−2PPA、UA−NDP;サートマー製CN962、CN963、CN964、CN965、CN980、CN981、CN982、CN983、CN996、CN9001、CN9002、CN9788、CN9893、CN978、CN9782、CN9783;東亞合成化学工業製M−1100、M−1200、M−1210、M−1310、M−1600;根上工業製アートレジンUN−9000PEP、UN−9200A、UN−7600、UN−333、UN−1255、UN−6060PTM、UN−6060P、SH−500B;共栄社化学製AH−600、AT−600;ダイセル・オルネクス製エベクリル280、エベクリル284、エベクリル402、エベクリル8402、エベクリル9270などがある。 Examples of commercially available bifunctional urethane (meth) acrylates include U-108A, U-200AX, UA-112P, UA-5201, U-340AX, UA-511, UA-512, and UA- manufactured by Shin-Nakamura Chemical Industries. 311, UA-412A, UA-4200, UA-4400, UA-340P, UA-2235PE, UA-160TM, UA-6100, U-108, UA-4000, UA-122P, UA-5201, UA-512, UA-W2, UA-7000, U-2PPA, UA-NDP; Sartmer CN962, CN963, CN964, CN965, CN980, CN981, CN982, CN983, CN996, CN9001, CN9002, CN9788, CN9893, CN978, CN9782, CN9783; M-1100, M-1200, M-1210, M-1310, M-1600 manufactured by Toa Synthetic Chemical Industry; Art Resins UN-99000PEP, UN-9200A, UN-7600, UN-333, UN-1255, manufactured by Negami Industrial Co., Ltd. UN-6060PTM, UN-6060P, SH-500B; AH-600, AT-600 manufactured by Kyoeisha Chemical Co., Ltd.;
三官能ウレタン(メタ)アクリレートの市販品の例には、ダイセル・オルネクス社製エベクリル4513、エベクリル4740、KRM8296、エベクリル8296、エベクリル8311を挙げることができる。 Examples of commercially available products of trifunctional urethane (meth) acrylate include Evekryl 4513, Evekryl 4740, KRM8296, Evekryl 8296, and Evekryl 8311 manufactured by Daicel Ornex.
(A)ウレタン(メタ)アクリレートは上記のうちの1種類を用いても、複数種類の組み合わせとしてもよい。 As the urethane (meth) acrylate, one of the above may be used, or a combination of a plurality of types may be used.
(A)ウレタン(メタ)アクリレートの使用量は、硬化性組成物の総質量に対して、30〜40質量%、特に34〜36%の範囲にあると好ましい。
上記の割合の(A)ウレタン(メタ)アクリレートを用いることより、硬化性組成物を施与する基板に対する密着性と、硬化塗膜の柔軟性が向上する。
The amount of the urethane (meth) acrylate used (A) is preferably in the range of 30 to 40% by mass, particularly 34 to 36%, based on the total mass of the curable composition.
By using the above ratio (A) urethane (meth) acrylate, the adhesion to the substrate to which the curable composition is applied and the flexibility of the cured coating film are improved.
[(B)チオカルボン酸誘導体]
本発明の硬化性組成物は(B)チオカルボン酸誘導体を、(A)ウレタン(メタ)アクリレート100質量部に対して50質量部以上、好ましくは60〜120質量部の範囲で含む。
本発明では(B)チオカルボン酸誘導体を含むことにより、硬化塗膜の光線透過率を向上させることができる。(B)チオカルボン酸誘導体は、1種類を単独で使用しても2種類以上併用してもよい。
[(B) Thiocarboxylic acid derivative]
The curable composition of the present invention contains (B) a thiocarboxylic acid derivative in an amount of 50 parts by mass or more, preferably 60 to 120 parts by mass with respect to 100 parts by mass of (A) urethane (meth) acrylate.
In the present invention, the light transmittance of the cured coating film can be improved by containing the (B) thiocarboxylic acid derivative. (B) The thiocarboxylic acid derivative may be used alone or in combination of two or more.
(B)チオカルボン酸誘導体としては、
その具体例としては、β-メルカプトプロピオン酸、2−エチルヘキシル−3-メルカプトプロピオネート、n−オクチル-3−メルカプトプロピオネート、メトキシブチル−3−メルカプトプロピオネート、ステアリル-3-メルカプトプロピオネート、トリメチロールプロパン トリス(3−メルカプトプロピオネート)プロピオネート、ペンタエリスリトール テトラキス(3−メルカプトプロピオネート)、テトラエチレングリコール ビス(3−メルカプトプロピオネート)等の直鎖または分岐状の化合物、及びトリス−[(3−メルカプトプロピオニルオキシ)− エチル]−イソシアヌレートなどの環状構造を有する化合物を含むメルカプトプロピオン酸誘導体を挙げることができ、本発明ではトリス−[(3−メルカプトプロピオニルオキシ)− エチル]−イソシアヌレートが特に好ましく用いられる。
(B) As a thiocarboxylic acid derivative,
Specific examples thereof include β-mercaptopropionic acid, 2-ethylhexyl-3-mercaptopropionate, n-octyl-3-mercaptopropionate, methoxybutyl-3-mercaptopropionate, and stearyl-3-mercaptopropionate. Linear or branched compounds such as pionate, trimetylolpropane tris (3-mercaptopropionate) propionate, pentaerythritol tetrakis (3-mercaptopropionate), tetraethylene glycol bis (3-mercaptopropionate) , And tris-[(3-mercaptopropionyloxy) -ethyl] -mercaptopropionic acid derivatives containing compounds having a cyclic structure such as isocyanurate, and in the present invention, tris-[(3-mercaptopropionyloxy) -Ethyl] -isocyanurate is particularly preferably used.
(B)チオカルボン酸誘導体の使用量は、硬化性組成物の総質量に対して、25〜40質量%、特に30〜38%の範囲にあると好ましい。
(B)チオカルボン酸誘導体の使用量を25質量%以上とすることにより、硬化塗膜の光線透過率が十分に得られ、40質量%以下とすることによりウレタン(メタ)アクリレート単独よりも、硬化性組成物の基板に対する密着性をより得ることができる。
The amount of the thiocarboxylic acid derivative used (B) is preferably in the range of 25 to 40% by mass, particularly 30 to 38%, based on the total mass of the curable composition.
(B) When the amount of the thiocarboxylic acid derivative used is 25% by mass or more, sufficient light transmittance of the cured coating film can be obtained, and when it is 40% by mass or less, it is cured more than urethane (meth) acrylate alone. It is possible to obtain better adhesion of the sex composition to the substrate.
[(C)トリアリルイソシアヌレート]
本発明の硬化性組成物は、(C)トリアリルイソシアヌレートを、(A)ウレタン(メタ)アクリレート100質量部に対して40質量部以上、好ましくは45〜95質量部の範囲で含む。
一般に、トリアリルイソシアヌレートは、硬化性組成物に対して、10質量%程度の少量を添加することにより、架橋助剤としての作用および硬化性組成物における密着性付与剤としての作用を奏するものであるが、本発明では(C)トリアリルイソシアヌレートを40質量部以上用いることにより硬化塗膜のヘーズ値を低下させ、および光線透過率を高水準とし、耐熱性も付与することができる。
(C)トリアリルイソシアヌレートの使用量は、硬化性組成物の総質量に対して、20〜40質量%、特に24〜33%の範囲にあると好ましい。
(C)トリアリルイソシアヌレートの使用量を20質量%以上とすることにより、硬化塗膜の硬度を十分とすることが可能となり、40質量%以下とすることにより、透明性および光線透過率が特に良好となり、耐熱性も付与することができる。
[(C) Triallyl Isocyanurate]
The curable composition of the present invention contains (C) triallyl isocyanurate in an amount of 40 parts by mass or more, preferably 45 to 95 parts by mass with respect to 100 parts by mass of (A) urethane (meth) acrylate.
In general, triallyl isocyanurate acts as a cross-linking aid and an adhesion-imparting agent in a curable composition by adding a small amount of about 10% by mass to the curable composition. However, in the present invention, by using (C) triallyl isocyanurate in an amount of 40 parts by mass or more, the haze value of the cured coating film can be lowered, the light transmittance can be made high, and heat resistance can be imparted.
The amount of triallyl isocyanurate (C) used is preferably in the range of 20 to 40% by mass, particularly 24 to 33%, based on the total mass of the curable composition.
(C) When the amount of triallyl isocyanurate used is 20% by mass or more, the hardness of the cured coating film can be made sufficient, and when it is 40% by mass or less, the transparency and the light transmittance are improved. It becomes particularly good, and heat resistance can be imparted.
[(D)光重合開始剤]
本発明の硬化性組成物は(D)光重合開始剤を含む。使用可能な光重合開始剤の例としては、例えば、ベンゾイン、ベンジル、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインn−プロピルエーテル、ベンゾインイソプロピルエーテル、ベンゾインn−ブチルエーテルなどのベンゾイン類;ベンゾインアルキルエーテル類;ベンゾフェノン、p−メチルベンゾフェノン、ミヒラーズケトン、メチルベンゾフェノン、4,4’−ジクロロベンゾフェノン、4,4’−ビスジエチルアミノベンゾフェノンなどのベンゾフェノン類;アセトフェノン、α- ヒドロキシアセトフェノン、2,2−ジメトキシ−2−フェニルアセトフェノン、2,2−ジエトキシ−2−フェニルアセトフェノン、1,1−ジクロロアセトフェノン、1−ヒドロキシシクロヘキシルフェニルケトン、2−メチル−[4−(メチルチオ)フェニル]−2−モルフォリノ−1−プロパノン、N,N−ジメチルアミノアセトフェノン、などのアセトフェノン類;2,4−ジメチルチオキサントン、2,4−ジエチルチオキサントン、2−クロロチオキサントン、2,4−ジイソプロピルチオキサントンなどのチオキサントン類;アントラキノン、クロロアントラキノン、2−メチルアントラキノン、2−エチルアントラキノン、2−tert−ブチルアントラキノン、1−クロロアントラキノン、2−アミルアントラキノン、2−アミノアントラキノンなどのアントラキノン類;アセトフェノンジメチルケタール、ベンジルジメチルケタールなどのケタール類;エチル−4−ジメチルアミノベンゾエート、2−(ジメチルアミノ)エチルベンゾエート、p−ジメチル安息香酸エチルエステルなどの安息香酸エステル類;フェニルジスルフィド2−ニトロフルオレン、ブチロイン、アニソインエチルエーテル、アゾビスイソブチロニトリル、テトラメチルチウラムジスルフィド等を挙げることができる。
[(D) Photopolymerization Initiator]
The curable composition of the present invention contains (D) a photopolymerization initiator. Examples of usable photopolymerization initiators include benzoins such as benzoin, benzyl, benzoin methyl ether, benzoin ethyl ether, benzoin n-propyl ether, benzoin isopropyl ether, benzoin n-butyl ether; benzoin alkyl ethers; Benthraquinones such as benzophenone, p-methylbenzophenone, Michelers ketone, methylbenzophenone, 4,4'-dichlorobenzophenone, 4,4'-bisdiethylaminobenzophenone; acetophenone, α-hydroxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone , 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 1-hydroxycyclohexylphenylketone, 2-methyl- [4- (methylthio) phenyl] -2-morpholino-1-propanone, N, N -Acetophenones such as dimethylaminoacetophenone; thioxanthons such as 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-diisopropylthioxanthone; anthraquinone, chloroanthraquinone, 2-methylanthraquinone, Anthraquinones such as 2-ethylanthraquinone, 2-tert-butyl anthraquinone, 1-chloroanthraquinone, 2-amyl anthraquinone, 2-aminoanthraquinone; ketals such as acetphenone dimethyl ketal and benzyl dimethyl ketal; ethyl-4-dimethylaminobenzoate , 2- (Dimethylamino) ethylbenzoate, benzoic acid esters such as p-dimethylbenzoic acid ethyl ester; phenyldisulfide 2-nitrofluorene, butyroin, anthraquinone ethyl ether, azobisisobutyronitrile, tetramethylthium disulfide, etc. Can be mentioned.
上記(D)光重合開始剤は、1種もしくは2種以上を組み合わせて用いることができるが、硬化物の柔軟性を損なわずに表面特性を向上させるためにα- ヒドロキシアセトフェノン系の光重合開始剤を用いることが好ましい。 The above (D) photopolymerization initiator can be used alone or in combination of two or more, but in order to improve the surface properties without impairing the flexibility of the cured product, α-hydroxyacetophenone-based photopolymerization initiator is initiated. It is preferable to use an agent.
(D)光重合開始剤は、(A)ウレタン(メタ)アクリレート100質量部に対して、好ましくは0.1〜10質量部、より好ましくは0.3〜5質量部の割合で添加される
。
The photopolymerization initiator (D) is added at a ratio of preferably 0.1 to 10 parts by mass, more preferably 0.3 to 5 parts by mass, based on 100 parts by mass of the urethane (meth) acrylate (A). ..
上述の(A)ウレタン(メタ)アクリレート、前記(B)チオカルボン酸誘導体、及び前記(C)トリアリルイソシアヌレートの合計質量は、硬化性組成物の全体の質量の95%以上であることが好ましく、これにより、高い全光線透過率および良好に抑制された曇り度という特性を得ることができる。 The total mass of the above-mentioned (A) urethane (meth) acrylate, the above-mentioned (B) thiocarboxylic acid derivative, and the above-mentioned (C) triallyl isocyanurate is preferably 95% or more of the total mass of the curable composition. As a result, the characteristics of high total light transmittance and well-suppressed cloudiness can be obtained.
粘度調整には、公知慣用の希釈剤、特に反応性希釈剤を用いることができる。特に分子中に1個のエチレン性不飽和基を有する化合物である単官能(メタ)アクリレート化合物が、希釈効果が高く好ましい。 A known and commonly used diluent, particularly a reactive diluent, can be used for adjusting the viscosity. In particular, a monofunctional (meth) acrylate compound, which is a compound having one ethylenically unsaturated group in the molecule, has a high dilution effect and is preferable.
[その他の成分]
本発明の硬化性組成物には、本発明の効果を損なわない範囲で、前記成分以外の他の成分を添加することができる。添加剤としては、光硬化性モノマー、シリコーン系、フッ素系の消泡剤、レベリング剤、公知慣用の熱重合禁止剤、紫外線吸収剤、シランカップリング剤、可塑剤、発泡剤、難燃剤、帯電防止剤、老化防止剤、抗菌・防黴剤等を配合することができる。
[Other ingredients]
In addition to the above-mentioned components, components other than the above-mentioned components can be added to the curable composition of the present invention as long as the effects of the present invention are not impaired. Additives include photocurable monomers, silicone-based and fluorine-based defoamers, leveling agents, known and commonly used thermal polymerization inhibitors, UV absorbers, silane coupling agents, plasticizers, foaming agents, flame retardants, and antistatic agents. An inhibitor, an antistatic agent, an antibacterial / antifungal agent, etc. can be blended.
本発明の硬化性組成物は、所望の特性を損なわない範囲であれば、熱硬化性成分を含んでもよいが、一般には熱硬化成分は用いない。その結果、より優れた透明性および光線透過性を有し、経時変化の少ない硬化物とすることができる。 The curable composition of the present invention may contain a thermosetting component as long as it does not impair the desired properties, but generally does not use a thermosetting component. As a result, it is possible to obtain a cured product having more excellent transparency and light transmittance and having little change with time.
本発明の硬化性組成物は、基板との密着性が高いため、基板との結合が容易かつ確実となり、結合対象とされる機器や部品の耐久性も向上させることができる。 Since the curable composition of the present invention has high adhesion to the substrate, it can be easily and surely bonded to the substrate, and the durability of the equipment or parts to be bonded can be improved.
[硬化性組成物の硬化方法]
上述の成分から構成される本発明の硬化性組成物は、光硬化することにより硬化物とすることができる。硬化に際しては、硬化性組成物を石英ガラス等の基材などに塗工後、活性エネルギー線を照射し、硬化するものである。なお、本発明の硬化性組成物は、1〜50dPa・sの粘度を有することが好ましい。
[Curing method of curable composition]
The curable composition of the present invention composed of the above-mentioned components can be made into a cured product by photocuring. At the time of curing, the curable composition is applied to a base material such as quartz glass and then irradiated with active energy rays to cure. The curable composition of the present invention preferably has a viscosity of 1 to 50 dPa · s.
塗工方法は、ディップコート法、フローコート法、バーコーター法、スクリーン印刷法、の任意の方法を適用することができる。また、活性エネルギー線の照射光源としては、低圧水銀灯、中圧水銀灯、高圧水銀灯、超高圧水銀灯、キセノンランプ又はメタルハライドランプなどが適当である。その他、UV−LED、レーザー光線、電子線なども活性エネルギー線として利用できる。 As the coating method, any method such as a dip coating method, a flow coating method, a bar coater method, and a screen printing method can be applied. Further, as the irradiation light source of the active energy ray, a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a xenon lamp, a metal halide lamp and the like are suitable. In addition, UV-LED, laser beam, electron beam and the like can also be used as active energy rays.
[硬化性組成物の硬化・成形方法]
ここで、表面に凹部を有する版体を用いて、本発明の硬化性組成物を凹部に充填し、充填した硬化性組成物を紫外線により硬化させ、その硬化物を凹部から取り出すことにより成型品を得る方法について図面を用いて例示する。
[Curing / molding method of curable composition]
Here, using a plate having recesses on the surface, the curable composition of the present invention is filled in the recesses, the filled curable composition is cured by ultraviolet rays, and the cured product is taken out from the recesses to form a molded product. The method of obtaining the above will be illustrated with reference to the drawings.
図1は、表面に凹部(2)を有した版体(1)を示している。一般的には、ステンレスなどの金属製のものが用いられる。 FIG. 1 shows a plate (1) having a recess (2) on its surface. Generally, a metal material such as stainless steel is used.
図2は、この版体に本発明の硬化性組成物を充填した状態(3)を示している。一般的には、ドクターナイフなどを用いて硬化性組成物を版体の凹部へ充填する。 FIG. 2 shows a state (3) in which this plate is filled with the curable composition of the present invention. Generally, the curable composition is filled into the recesses of the plate using a doctor knife or the like.
図3は、その上部から基材(4)を被せ、さらにその上部の光源(5)から紫外線を照射して本発明の硬化性組成物を硬化させる工程を示している。一般的に、基材(4)には紫外線を透過する透明なポリエチレンテレフタレートやポリカーボネート製のフィルムが用いられる。 FIG. 3 shows a step of covering the base material (4) from the upper part thereof and irradiating the light source (5) on the upper part with ultraviolet rays to cure the curable composition of the present invention. Generally, a transparent polyethylene terephthalate or polycarbonate film that transmits ultraviolet rays is used as the base material (4).
図4は、硬化物を版体(1)から離型し硬化成型体(6)を得た状態を示している。図1から図4の一連の工程は、それぞれに専用の公知の装置を用いることで、連続的に成型品を製造することができる。 FIG. 4 shows a state in which the cured product is separated from the plate (1) to obtain a cured molded product (6). By using a known device dedicated to each of the series of steps of FIGS. 1 to 4, a molded product can be continuously manufactured.
このように本発明の硬化性組成物を予め成型して用いることができる。凹部に充填したままの光硬化による成型方法では、酸素による硬化阻害がないため、厚みを増すことができ、最厚部で厚さ5mmとすることも可能である。
なお、本発明の硬化性組成物は、タッチパネル等などの透明スクリーン用、並びにソルダーレジスト、層間絶縁材、およびカバーレイなどの絶縁材料として適用することもできる。また、本発明の硬化性組成物は、ソルダーダムとして適用してもよい。更に、本発明の組成物は良好な密着性を有することから、接着剤、特に透明スクリーン等に用いられる無色透明の接着剤として用いることもできる。
As described above, the curable composition of the present invention can be molded and used in advance. In the molding method by photocuring while the recesses are filled, the thickness can be increased because the curing is not hindered by oxygen, and the thickness of the thickest portion can be 5 mm.
The curable composition of the present invention can also be applied to transparent screens such as touch panels, and as insulating materials such as solder resists, interlayer insulating materials, and coverlays. Further, the curable composition of the present invention may be applied as a solder dam. Furthermore, since the composition of the present invention has good adhesion, it can also be used as an adhesive, particularly a colorless and transparent adhesive used for transparent screens and the like.
以下、実施例、比較例により、本発明をさらに詳細に説明する。本発明は、下記実施例に限定されるものではなく、以下に記載の「部」及び「%」とは、特に断りのない限り全て質量基準とする。 Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. The present invention is not limited to the following examples, and the "parts" and "%" described below are all based on mass unless otherwise specified.
[実施例1〜10および比較例1〜3]
下記表1記載の各成分を自転・公転式ミキサーにより混錬し、各硬化性組成物を調製した。
得られた各硬化性組成物を以下の評価を行った。
[Examples 1 to 10 and Comparative Examples 1 to 3]
Each component shown in Table 1 below was kneaded with a rotating / revolving mixer to prepare each curable composition.
Each of the obtained curable compositions was evaluated as follows.
1.印刷性評価
実施例1〜10および比較例1〜3の硬化性組成物を、ポリエステル(テトロン(登録商標))製の300メッシュの刷版を具備したスクリーン印刷装置により、硬化後の膜厚10μmとなるように石英ガラスの基板上に全面印刷した。
印刷後5分経過後の塗膜の表面状態を目視にて観察し、以下の基準で評価を行った。結果を表1に示す。
1. 1. Printability Evaluation The curable compositions of Examples 1 to 10 and Comparative Examples 1 to 3 were cured to a thickness of 10 μm by a screen printing apparatus equipped with a 300 mesh printing plate made of polyester (Tetron (registered trademark)). The entire surface was printed on a quartz glass substrate so as to be.
The surface condition of the
〇 硬化性組成物により基板全面が滑らか、かつ均一に塗工されている
× 硬化性組成物の表面に気泡の破裂の痕が見られ、塗膜表面が不均一
〇 The entire surface of the substrate is coated smoothly and evenly with the curable composition. × The surface of the curable composition shows traces of bursting bubbles, and the surface of the coating film is non-uniform.
2.指触乾燥性評価(タック評価)
実施例1〜10および比較例1〜3の硬化性組成物を、ポリエステル(テトロン(登録商標))製の300メッシュの刷版を具備したスクリーン印刷装置により、石英ガラスの基板上に全面印刷した。得られた塗膜を、メタルハライドランプを用いて1000mJ/cm2の光量で露光し、塗膜を硬化させた。これにより得られた塗膜(膜厚10μm)を評価用の硬化膜として用い、下記の基準で評価した。結果を表1に示す。
2. 2. Evaluation of dryness to the touch (tack evaluation)
The curable compositions of Examples 1 to 10 and Comparative Examples 1 to 3 were entirely printed on a quartz glass substrate by a screen printing apparatus equipped with a 300 mesh printing plate made of polyester (Tetron (registered trademark)). .. The obtained coating film was exposed to a light amount of 1000 mJ / cm 2 using a metal halide lamp to cure the coating film. The coating film (thickness 10 μm) thus obtained was used as a cured film for evaluation and evaluated according to the following criteria. The results are shown in Table 1.
◎ 塗膜を指で触っても塗膜表面に指紋が付かず、指に塗膜が付着することもない
〇 塗膜を指で触ると塗膜表面に指紋がつくが、指に塗膜が付着はしない
× 塗膜を指で触ると塗膜表面に指紋が付き、更に指に塗膜が付着した
◎ Even if you touch the coating film with your finger, no fingerprints will be attached to the surface of the coating film, and the coating film will not adhere to your fingers. Does not adhere × When the coating film is touched with a finger, a fingerprint is attached to the surface of the coating film, and the coating film further adheres to the finger.
3.鉛筆硬度評価
上記2.指触乾燥性評価で用いた評価用の硬化膜と同様の効果膜を作製し、その表面硬度を鉛筆硬度試験器( (株)東洋精機製作所 製 )を用いて測定した。この試験では、各試験片に、芯の先が平らになるように研がれた3H、および4Hの鉛筆を、約45°の角度、1kg荷重にて押圧した状態で、0.5〜1mm/sの速度で少なくとも7mm移動させることにより距離塗膜の剥がれの状態を以下の基準で評価した。結果を表1に示す。
3. 3. Pencil hardness evaluation Above 2. An effect film similar to the cured film for evaluation used in the evaluation of dryness to the touch was prepared, and the surface hardness thereof was measured using a pencil hardness tester (manufactured by Toyo Seiki Seisakusho Co., Ltd.). In this test, each test piece was pressed with a 3H and 4H pencil sharpened so that the tip of the core was flat, at an angle of about 45 ° and with a load of 1 kg, and was 0.5 to 1 mm. By moving at least 7 mm at a speed of / s, the state of peeling of the distance coating film was evaluated according to the following criteria. The results are shown in Table 1.
◎ 4Hの鉛筆で塗膜の剥がれなし
〇 3Hの鉛筆で塗膜の剥がれなし
× 3Hの鉛筆で塗膜が剥がれる
◎ No peeling of the coating film with a 4H pencil 〇 No peeling of the coating film with a 3H pencil × Peeling of the coating film with a 3H pencil
4.密着性評価
上記3.鉛筆硬度評価に用いたものと同様の硬化塗膜(膜厚10μm)の密着性を、JIS K 5600−5−6に準拠し、クロスカットガイドを用いて10mmx10mm碁盤目状にクロスカットを入れて100x100個の碁盤目を形成することにより、クロスカットテープピールリング試験を実施した。碁盤目の残り個数を、以下の基準で目視観察した。結果を表1に示す。
4. Adhesion evaluation Above 3. Adhesion of the cured coating film (thickness 10 μm) similar to that used for pencil hardness evaluation is based on JIS K 5600-5-6, and a cross cut is made in a 10 mm x 10 mm grid pattern using a cross cut guide. A cross-cut tape peel ring test was performed by forming 100x100 grids. The remaining number of grids was visually observed according to the following criteria. The results are shown in Table 1.
〇 塗膜の碁盤目に剥がれが全くない
× 塗膜の碁盤目の1個以上に剥がれが観察された
〇 No peeling on the grid of the coating film × Peeling was observed on one or more of the grids of the coating film
5.全光線透過率評価
上記3.鉛筆硬度評価に用いたものと同様の硬化塗膜(膜厚10μm)について、全光線透過率透過率を、JIS K 7361‐1に準拠し、紫外可視分光光度計V−670EX(日本分光社製)を用いることにより測定した。
この評価では評価に用いた波長300〜780nmの全域にわたる入射光に対する透過光の割合を示す。測定結果を表1に記載した。
5. Evaluation of total light transmittance Above 3. For a cured coating film (thickness 10 μm) similar to that used for pencil hardness evaluation, the total light transmittance is based on JIS K 7361-1, and the ultraviolet-visible spectrophotometer V-670EX (manufactured by JASCO Corporation). ) Was used.
In this evaluation, the ratio of transmitted light to incident light over the entire wavelength range of 300 to 780 nm used in the evaluation is shown. The measurement results are shown in Table 1.
6.ヘーズ(曇価)評価
上記3.鉛筆硬度評価に用いたものと同様の硬化塗膜(膜厚10μm)について、JIS K 7136に準拠して、紫外可視分光光度計V−670EX(日本分光社製)を用いることにより測定した。なお、JIS K 7136に記載されているとおり、ヘーズとは試験片の散乱光線透過率を全光線透過率で割った値の100分率で表される値であるところ、全光線透過率の値はJIS K 7361-1に準拠して求めた。測定結果を表1に記載したる。
6. Haze (cloudiness) evaluation Above 3. A cured coating film (thickness 10 μm) similar to that used for pencil hardness evaluation was measured by using an ultraviolet-visible spectrophotometer V-670EX (manufactured by JASCO Corporation) in accordance with JIS K 7136. As described in JIS K 7136, the haze is a value expressed as a percentage of the value obtained by dividing the scattered light transmittance of the test piece by the total light transmittance, and is a value of the total light transmittance. Was obtained in accordance with JIS K 7361-1. The measurement results are shown in Table 1.
7.耐熱性試験(加熱処理後の全光線透過率およびヘーズ評価)
7−1.加熱処理試料の作製
上記3.鉛筆硬度評価に用いたものと同様の硬化塗膜を、温度100℃、の熱風循環式乾燥炉に2時間保管することにより、加熱処理試料を作製した。
7−2.加熱処理試料の全光線透過率評価およびヘーズ評価
これにより得られた加熱処理試料についての全光線透過率透過及びヘーズ値を、上記の5.全光線透過率評価および6.ヘーズ(曇価)評価と同様の測定方法により求めた。測定結果を表1に記載する。
7. Heat resistance test (total light transmittance and haze evaluation after heat treatment)
7-1. Preparation of heat-treated sample
Above 3. A heat-treated sample was prepared by storing a cured coating film similar to that used for pencil hardness evaluation in a hot air circulation type drying oven at a temperature of 100 ° C. for 2 hours.
7-2. Evaluation of total light transmittance and haze of the heat-treated sample The total light transmittance transmission and haze value of the heat-treated sample obtained by this are evaluated in the above 5. Evaluation of total light transmittance and 6. It was determined by the same measurement method as the haze (cloud value) evaluation. The measurement results are shown in Table 1.
8.耐候性試験(露光処理後の全光線透過率およびヘーズ評価)
8−1.露光処理試料の作製
上記3.鉛筆硬度評価に用いたものと同様の硬化塗膜に対し、メタルハライドランプにより20J/cm2の光量の全面露光を行うことにより、露光処理試料を作製した。
8−2.露光処理試料の全光線透過率評価およびヘーズ評価
これにより得られた露光処理試料についての全光線透過率透過及びヘーズ値を、上記の5.全光線透過率評価および6.ヘーズ(曇価)評価と同様の測定方法により求めた。測定結果を表1に記載する。
8. Weather resistance test (total light transmittance and haze evaluation after exposure treatment)
8-1. Preparation of exposed sample
Above 3. An exposure-treated sample was prepared by subjecting a cured coating film similar to that used for pencil hardness evaluation to an entire surface with a light amount of 20 J / cm 2 using a metal halide lamp.
8-2. Evaluation of total light transmittance and haze of the exposed sample The total light transmittance transmission and haze value of the exposed sample obtained by this are evaluated in the above 5. Evaluation of total light transmittance and 6. It was determined by the same measurement method as the haze (cloud value) evaluation. The measurement results are shown in Table 1.
表中に記載した材料の詳細を以下に示す。
エベクリル8402:2官能ウレタンアクリレート、光硬化性ウレタン樹脂、ダイセル・オルネクス株式会社製
TAIC:シアヌル酸トリアリル、三菱ケミカル株式会社製
TEMPIC:トリス‐[(3−メルカプトプロピオニルオキシ)−エチル]−イソシアヌレート、SC有機化学株式会社製
Omnirad(登録商標)184:1-ヒドロキシシクロヘキシル-フェニルケトン、IGM Resins社製
KBM−5103:3−アクリロキシプロピルトリメトキシシラン、信越化学工業株式会社製
ライトエステルP−1M:モノ(2−ヒドロキシエチルメタクリレート)ホスフェート、共栄社化学株式会社製
フローレン AC−2300C:オレフィンポリマー(消泡剤)、共栄社化学株式会社製
ポリフローKL−700:シリコーン含有ポリマー(基材湿潤剤)、共栄社化学株式会社製
Details of the materials listed in the table are shown below.
Evecryl 8402: Bifunctional urethane acrylate, photocurable urethane resin, Taisel Ornex Co., Ltd. TAIC: Triallyl cyanurate, Mitsubishi Chemical Co., Ltd. TEMPIC: Tris-[(3-mercaptopropionyloxy) -ethyl] -isocyanurate, Polymer (registered trademark) 184: 1-hydroxycyclohexyl-phenylketone manufactured by SC Organic Chemical Co., Ltd., KBM-5103: 3-acryloxypropyltrimethoxysilane manufactured by IGM Resins, light ester P-1M manufactured by Shinetsu Chemical Industry Co., Ltd .: Mono (2-hydroxyethyl methacrylate) phosphate, Floren AC-2300C manufactured by Kyoeisha Chemical Co., Ltd .: Olefin polymer (antifoaming agent), Polyflow KL-700 manufactured by Kyoeisha Chemical Co., Ltd .: Silicone-containing polymer (base material wetting agent), Kyoeisha Chemical Co., Ltd. Made by Co., Ltd.
以上より、本発明の硬化性組成物は 印刷性に優れ、その硬化物は指触乾燥性、鉛筆硬度、密着性のいずれの特性においても優れた物理的特性を有することがわかる。
更に、本発明の硬化物は、光線透過率が初期値、並びに耐熱試験暴露後および対候性試験暴露後のいずれも99.0%以上と高く、ヘーズ値も、初期値、並びに耐熱試験暴露後および対候性試験暴露後のいずれにおいても1.5%以下と抑制されていることから、特に液晶ディスプレイやタッチパネル等の透明保護材料として、初期の無色透明の美しい状態が長期の過酷な使用にも耐性を有することがわかる。
From the above, it can be seen that the curable composition of the present invention is excellent in printability, and the cured product has excellent physical properties in all of the properties of touch-drying property, pencil hardness, and adhesion.
Further, the cured product of the present invention has a high light transmittance of 99.0% or more after exposure to the heat resistance test and after exposure to the weather resistance test, and the haze value is also the initial value and the heat resistance test exposure. Since it is suppressed to 1.5% or less both after and after exposure to the weather resistance test, the initial colorless and transparent beautiful state is used for a long period of time, especially as a transparent protective material for liquid crystal displays and touch panels. It can be seen that it is also resistant to.
本発明は上記の実施の形態の構成及び実施例に限定されるものではなく、発明の要旨の範囲内で種々変形が可能である。 The present invention is not limited to the configuration and examples of the above-described embodiment, and various modifications can be made within the scope of the gist of the invention.
1・・・版体
2・・・凹部
3・・・光硬化性組成物
4・・・基材
5・・・光源
6・・・成型品
1 ...
Claims (3)
(B)チオカルボン酸誘導体、
(C)トリアリルイソシアヌレート、および
(D)光重合開始剤、
を含む硬化性組成物であって、
前記(A)ウレタン(メタ)アクリレート100質量部に対して前記(B)チオカルボン酸誘導体を50質量部以上、
前記(A)ウレタン(メタ)アクリレート100質量部に対して前記(C)トリアリルイソシアヌレートを40質量部以上含むことを特徴とする硬化性組成物。 (A) Urethane (meth) acrylate,
(B) Thiocarboxylic acid derivative,
(C) Triallyl isocyanurate, and (D) Photopolymerization initiator,
A curable composition comprising
50 parts by mass or more of the (B) thiocarboxylic acid derivative with respect to 100 parts by mass of the (A) urethane (meth) acrylate.
A curable composition comprising 40 parts by mass or more of the (C) triallyl isocyanurate with respect to 100 parts by mass of the (A) urethane (meth) acrylate.
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KR1020217031907A KR102718117B1 (en) | 2019-03-27 | 2019-12-05 | Curable composition and cured product thereof |
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