CN107722916A - UV-curable resin composition - Google Patents
UV-curable resin composition Download PDFInfo
- Publication number
- CN107722916A CN107722916A CN201710576642.XA CN201710576642A CN107722916A CN 107722916 A CN107722916 A CN 107722916A CN 201710576642 A CN201710576642 A CN 201710576642A CN 107722916 A CN107722916 A CN 107722916A
- Authority
- CN
- China
- Prior art keywords
- curable resin
- methyl
- resin compositions
- composition
- acrylate
- 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
- 239000011342 resin composition Substances 0.000 title claims abstract description 44
- 239000000853 adhesive Substances 0.000 claims abstract description 38
- 230000001070 adhesive effect Effects 0.000 claims abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 53
- 238000003848 UV Light-Curing Methods 0.000 claims description 42
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 24
- 229910000077 silane Inorganic materials 0.000 claims description 24
- GNBCKKSGQPLTRW-UHFFFAOYSA-N C(C=C)(=O)OC.C(N)(O)=O Chemical compound C(C=C)(=O)OC.C(N)(O)=O GNBCKKSGQPLTRW-UHFFFAOYSA-N 0.000 claims description 17
- 239000004973 liquid crystal related substance Substances 0.000 claims description 14
- 239000011521 glass Substances 0.000 claims description 13
- 239000004417 polycarbonate Substances 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 8
- 229920000515 polycarbonate Polymers 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- 230000008859 change Effects 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 3
- AJKZIPCWVAURSI-UHFFFAOYSA-N carbamic acid;2-methylprop-2-enoic acid Chemical compound NC(O)=O.CC(=C)C(O)=O AJKZIPCWVAURSI-UHFFFAOYSA-N 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000006087 Silane Coupling Agent Substances 0.000 abstract description 2
- 239000003999 initiator Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- -1 acryl Chemical group 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 9
- 238000003475 lamination Methods 0.000 description 9
- 230000007774 longterm Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000007711 solidification Methods 0.000 description 9
- 230000008023 solidification Effects 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000008929 regeneration Effects 0.000 description 8
- 238000011069 regeneration method Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229920002799 BoPET Polymers 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007767 bonding agent Substances 0.000 description 6
- 238000007731 hot pressing Methods 0.000 description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 description 3
- CTLDMRCJDQGAQJ-UHFFFAOYSA-N (1,1-dimethoxy-2-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(OC)(OC)CC1=CC=CC=C1 CTLDMRCJDQGAQJ-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000002313 adhesive film Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 102000054766 genetic haplotypes Human genes 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000005304 optical glass Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical class O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-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
- 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 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- SNZYOYGFWBZAQY-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methyloxirane Chemical compound CC1CO1.CCC(CO)(CO)CO SNZYOYGFWBZAQY-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical class CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical class CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 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 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
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- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
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- AWZKVJXQYAIKOD-UHFFFAOYSA-N but-2-ene carbamic acid Chemical group C(N)(O)=O.CC=CC AWZKVJXQYAIKOD-UHFFFAOYSA-N 0.000 description 1
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- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
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- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
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- 230000009257 reactivity Effects 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
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- 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
- 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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- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
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- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- C08G18/83—Chemically modified polymers
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- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5397—Phosphine oxides
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- C08K5/541—Silicon-containing compounds containing oxygen
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- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
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- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
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- C09J11/06—Non-macromolecular additives organic
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- C09J7/00—Adhesives in the form of films or foils
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- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/13363—Birefringent elements, e.g. for optical compensation
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- C08K5/5425—Silicon-containing compounds containing oxygen containing at least one C=C bond
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- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
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- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
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Abstract
The present invention relates to a UV-curable resin composition which can easily peel L CD from an adherend to regenerate L CD and can impart good adhesiveness even at normal temperature, and an adhesive sheet comprising the same.A solution to the present invention is a UV-curable resin composition comprising (A) a UV-curable prepolymer, (B) a UV-curable polyfunctional monomer, (C) a photopolymerization initiator, and (D) a silane coupling agent, wherein the component (A) is a urethane (meth) acrylate, the component (B) is 15 to 60 parts by mass, the component (C) is 0.5 parts by mass or more, and the component (D) is 0.1 to 5 parts by mass, per 100 parts by mass of the component (A).
Description
Technical field
The present invention relates to the UV curable resin compositions available for liquid crystal display display part and include its adhesive sheet
Material.
Background technology
At present, with the popularization of digitized electronic equipment, the display that liquid crystal display (LCD) has turned into fairly common fills
Put, and be used as LCD TV or PC displays, portable telephone terminal, portable game machine, desk-top electronic calculator, clock and watch
Etc. the display part of various equipment.Especially, in recent years, exist for the purpose for assigning 3D functions and be bonded on LCD
The liquid crystal display of the pattern polarizer formed by glass (patterning polarizing plate).
Herein, that the LCD for being bonded with polarizer is recovered after use, only LCD is recycled be present.Example
Such as, just require to peel off polarizer from LCD so that LCD regeneration (rework).Now, taken in conventional method by
LCD is integrally cooled down and (in other words, bonding agent cooled down), the method so as to which polarizer be peeled off from LCD.However, this method
In, the equipment for cooling is required, and it is good that workability, which can not be said,.Further, since polarizer is respectively provided with just with LCD
Property, therefore have the problem of breakage can occurs in either one when peeling off.That is, for conventional adhesive sheet, by LCD and phase
After potential difference plate bonding, easily peeled off and make LCD regeneration be difficult.
In order to solve above-mentioned such problem points, have studied even in normal temperature and adherend is thing hard as glass
The adhesive sheet that also can be easily peeled off in the case of matter.For example, a kind of clear adhesive is proposed in patent document 1
Film, the clear adhesive film contain bonding agent composition and produce the gas producing agent of gas by irradiating ultraviolet.In addition, specially
Heat and actinic ray curing type (light-cured type) adhesive composite are proposed in sharp document 2.
Prior art literature
Patent document
Patent document 1：Japanese Unexamined Patent Publication 2016-56244 publications
Patent document 2：Japanese Unexamined Patent Application Publication 2011-508814 publications
The content of the invention
The invention problem to be solved
However, for the clear adhesive film described in patent document 1, must be exposed in regeneration, in addition, specially
Actinic ray curing type (light-cured type) adhesive composite described in sharp document 2 is used in combination by being heated in regeneration
Silk thread (wire) cuts bonding agent to remove bonding agent.That is, following present situations be present：Not yet obtaining so far can not only
Ensure good cementability and the adhesive sheet that at normal temperatures easily can be peeled off LCD from adherend.
In view of the foregoing, it is an object of the invention to provide UV curable resin compositions and the adhesive sheet for including it
Material, for the UV curable resin compositions, even if easily can also shelling LCD from adherend at normal temperatures
From and regenerate LCD, and good cementability can be assigned.
Means for solving the problems
Present inventor is studied with keen determination in order to solve above-mentioned problem, as a result finds following UV curing types trees
Oil/fat composition can solve the problem that above-mentioned problem, and so as to complete the present invention, the UV curable resin compositions contain (A) UV solidifications
Type prepolymer, (B) UV curing types polyfunctional monomer, (C) Photoepolymerizationinitiater initiater and (D) silane coupler, (A) composition are
Carbamate (methyl) acrylate (urethane (meth) acrylate), relative to (A) described in 100 mass parts into
Point, the content of (B) composition be 15~60 mass parts, and the content of (C) composition is more than 0.5 mass parts, (D) into
The content divided is 0.1~5 mass parts.
That is, the present invention is as described below.
[1]
UV curable resin compositions, the UV curable resin compositions contain (A) UV curing types prepolymer, (B) UV
Curing type polyfunctional monomer, (C) Photoepolymerizationinitiater initiater and (D) silane coupler,
(A) composition is carbamate (methyl) acrylate,
Relative to (A) composition described in 100 mass parts, the content of (B) composition is 15~60 mass parts, (C)
The content of composition is that more than 0.5 mass parts the content of (D) composition is 0.1~5 mass parts.
[2]
UV curable resin compositions described in [1] as described above, wherein, carbamate (methyl) acrylate is
Selected from by carbamate (methyl) acrylate with polycarbonate backbone, the carbamate (first with polyether skeleton
Base) acrylate and with polyester backbone carbamate (methyl) acrylate form group in more than a kind.
[3]
UV curable resin compositions described in [1] or [2] as described above, wherein, carbamate (methyl) propylene
The weight average molecular weight of acid esters is 10,000~100,000, and double bond equivalent is 1,000~5,000g/eq.
[4]
UV curable resin compositions any one of [1]~[3] as described above, wherein, (B) the UV curing types are more
Functional monomer is (methyl) acrylic monomer with the functional group of more than 2.
[5]
UV curable resin compositions any one of [1]~[4] as described above, wherein, (C) photopolymerization triggers
Agent is acylphosphine oxide system Photoepolymerizationinitiater initiater.
[6]
UV curable resin compositions described in [5] as described above, wherein, acylphosphine oxide system Photoepolymerizationinitiater initiater is
2,4,6- trimethyl benzoyl diphenyl base phosphine oxides.
[7]
UV curable resin compositions any one of [1]~[6] as described above, wherein, (D) silane coupler
For the silane coupler with (methyl) acrylic acid series group ((meth) acryl group).
[8]
Adhesive sheet, the adhesive sheet include the UV gel-type resins combination any one of above-mentioned [1]~[7]
Thing.
[9]
Adhesive sheet described in [8] as described above, the dried thickness of the adhesive sheet is 10~250 μm.
[10]
3D liquid crystal panels, it is the 3D liquid crystal panels for being laminated LCD and pattern polarizer, wherein,
It is using the adhesive sheet described in above-mentioned [8] or [9] that the LCD is Nian Jie with the polarizer.
[11]
3D liquid crystal panels described in [10] as described above, wherein, the pattern polarizer is to form figuratum glass plate.
The effect of invention
For the adhesive sheet of the UV curable resin compositions comprising the present invention, even if can also hold at normal temperatures
Change places and LCD is peeled off from adherend and regenerates LCD, and good cementability can be assigned.
Embodiment
Hereinafter, the embodiment (hereinafter referred to as " present embodiment ") of the present invention is recorded in detail.Need what is illustrated
It is that the present invention is not limited to following embodiment, can carry out various modifications in the range of its purport and implement.
In the UV curable resin compositions of present embodiment,
Contain (A) UV curing types prepolymer, (B) UV curing types polyfunctional monomer, (C) Photoepolymerizationinitiater initiater and (D) silane
Coupling agent,
(A) composition is carbamate (methyl) acrylate,
Relative to (A) composition described in 100 mass parts, the content of (B) composition is 15~60 mass parts, (C)
The content of composition is that more than 0.5 mass parts the content of (D) composition is 0.1~5 mass parts.
[(A) UV curing types prepolymer]
The UV curable resin compositions of present embodiment include (A) UV curing types prepolymer (hereinafter also referred to as " and (A) into
Point ".).As long as UV curing types prepolymer is that carbamate structures are included in main chain, (methyl) acrylic acid is included in side chain
It is carbamate (methyl) acrylate of group, is not particularly limited.As carbamate (methyl) acrylic acid
Ester, it is not particularly limited, for example, carbamate (methyl) acrylate with polycarbonate backbone can be enumerated, with poly-
Carbamate (methyl) acrylate of ether skeleton, carbamate (methyl) acrylate with polyester backbone etc., its
In, from solidification adhesive sheet without xanthochromia from the viewpoint of, the carbamate (methyl) preferably with polycarbonate backbone
Acrylate.
Carbamate (methyl) acrylate with polycarbonate backbone refers to there is polycarbonate structure in main chain
There is the prepolymer of (methyl) acrylic acid series group with carbamate structures, in side chain.Amino with polycarbonate backbone
Formic acid esters (methyl) acrylate can for example be obtained by following manner：Make PCDL, diisocyanate and carboxylic acid two
Alcohol reacts, and it is reacted with (methyl) glycidyl acrylate.
The weight average molecular weight of PCDL is preferably 170~1,000, more preferably 300~700, further preferably
For 400~600.If the weight average molecular weight of PCDL is above range, existing can be to carbamate prepolymer master
Chain assigns the trend of the required film for regeneration.
As diisocyanate, it is not particularly limited, such as 2,4- toluene di-isocyanate(TDI)s (2,4-TDI), 2 can be enumerated,
6- toluene di-isocyanate(TDI)s (2,6-TDI), 4,4 '-methyl diphenylene diisocyanate (4,4 '-MDI), 2,4 '-diphenyl methane
Diisocyanate (2,4 '-MDI), 1,4- phenylene diisocyanates, xylylene diisocyanate (XDI), the methylene of durol two
Diisocyanate (TMXDI), dimethyl diphenyl diisocyanate (TODI, tolidine diisocyanate), 1,5- naphthalenes two are different
The aromatic isocyanates such as cyanate (NDI)；Hexamethylene diisocyanate (HDI), trimethyl hexamethylene diisocyanate
(TMHDI), the aliphatic polyisocyante such as lysine diisocyanate, norbornene alkyl diisocyanate (NBDI)；Trans- 1,4- rings
Ester ring type polyisocyanates such as hexyl diisocyanate, IPDI (IPDI), H6XDI (hydrogenation XDI) etc., its
In, from the viewpoint of optical characteristics (being not susceptible to xanthochromia), preferred hexamethylene diisocyanate.
As carboxylic acid glycol, it is not particularly limited, such as dimethylolpropionic acid, dihydromethyl propionic acid etc. can be enumerated.
Carbamate (methyl) acrylate with polyether skeleton refers to there is polyether structure and amino first in main chain
Acrylate structure, side chain have (methyl) acrylic acid series group prepolymer；Carbamate (methyl) with polyester backbone
Acrylate refers to, in main chain with polyester construction and carbamate structures, in side chain with (methyl) acrylic acid series group
Prepolymer.For above-mentioned prepolymer, except replacing PCDL using PTMEG, polyester-diol respectively
Outside, the available method same with above-mentioned carbamate (methyl) acrylate with polycarbonate backbone obtains.This
When, PTMEG, the preferable weight-average molecular weight of polyester-diol are identical with the preferable weight-average molecular weight of above-mentioned PCDL.
(A) weight average molecular weight of composition is preferably 10,000~100,000, more preferably 30, and 000~70,000, enter one
Step is preferably 40,000~60,000.If weight average molecular weight is above range, Film making properties be present, curability becomes good, length
Phase reliability becomes good trend.
Herein, weight average molecular weight refers to using the polystyrene standard that mean molecule quantity is about 500~about 1,000,000, utilized
Gel permeation chromatography (GPC) and the value measured.
(A) the double bond equivalent of composition is preferably 1,000~5,000g/eq, more preferably 1,500~2,500g/eq, enters one
Step is preferably 1,800~2,200g/eq.If double bond equivalent is above range, the influence of cure shrinkage is small, and long-term reliability is excellent
It is different, and exist solidification become easily, regeneration also become easy trend.
Herein, double bond equivalent refers to the solid state component quality (g)/(have using (methyl) acrylate containing carboxyl
The molal quantity of the compound of oxirane ring and ethylenic unsaturated bond) (g/mol) and the value that calculates.
(A) glass transition temperature (Tg) of composition is preferably -10~20 DEG C, more preferably -5~15 DEG C, further excellent
Elect 0~10 DEG C as.If glass transition temperature is above range, the harmony that long-term reliability and reproducibility be present becomes good
Good trend.
Herein, glass transition temperature refers to the value measured using Measurement of Dynamic Viscoelasticity (DMA).
[(B) UV curing types polyfunctional monomer]
The UV curable resin compositions of present embodiment include (B) UV curing types polyfunctional monomer (hereinafter also referred to as
" (B) composition ".).In order that LCD is renewable, it is necessary to viscoplasticity under improving normal temperature, in present embodiment, by solidifying to UV
UV curing type polyfunctional monomers are added in type prepolymer, so as to improve the crosslink density after solidification, are which thereby enhanced under normal temperature
Viscoplasticity.Herein, the viscoplasticity of UV curable resin compositions can be determined using Measurement of Dynamic Viscoelasticity (DMA), solidification
The store elastic modulus under normal temperature (25 DEG C) afterwards is preferably 1.0 × 108~1.0 × 1010Pa, more preferably 4.0 × 108~
5.0×109Pa, more preferably 6.0 × 108~3.0 × 109Pa。
As (B) composition, it is not particularly limited, such as (methyl) acrylic monomer can be enumerated, wherein, it is crosslinked from improving
Density, make from the viewpoint of reproducibility improves, preferred (methyl) acrylic monomer with the functional group of more than 2.
As (B) composition, specifically, as (B) composition with 2 functional groups, (the first of BDO two can be enumerated
Base) acrylate, ethylene glycol two (methyl) acrylate, glycerine two (methyl) acrylate, the propylene of Tricyclodecane Dimethanol two
Acid esters；As (B) composition with 3 functional groups, trimethylolpropane trimethacrylate, Pehanorm three can be enumerated
(methyl) acrylate, trimethylolpropane expoxy propane (trimethylolpropane propylene oxide) are modified
Three (methyl) acrylate；As (B) composition of the functional group with more than 4, dipentaerythritol four (methyl) third can be enumerated
Four ethylene-oxide-modified (methyl) acrylate of olefin(e) acid ester, pentaerythrite, pentaerythrite four (methyl) acrylate, Ji Wusi
Four ethylene-oxide-modified (methyl) acrylate of alcohol, double trimethylolpropane four (methyl) acrylate, dipentaerythritol six
Acrylate etc., wherein, from the viewpoint of reproducibility, preferred (methyl) acrylic acid series list with the functional group of more than 4
Body, the more preferably dipentaerythritol acrylate with 6 functional groups.
Relative to (A) composition of 100 mass parts, the content of (B) composition is 15~60 mass parts, preferably 18~40 mass
Part, more preferably 20~30 mass parts.If the content of (B) composition is less than 15 mass parts, the cementability after solidification is high, under normal temperature
Reproducibility be deteriorated, if more than 60 mass parts, cementability is insufficient, long-term reliability be deteriorated.In addition, the phase by (B) composition
In the case that content for (A) composition of 100 mass parts is adjusted to above-mentioned scope, the melt viscosity of resin combination
The advantages of being kept within the specific limits, therefore being not likely to produce uneven fitting, image disorder.
[(C) Photoepolymerizationinitiater initiater]
The UV curable resin compositions of present embodiment include (C) Photoepolymerizationinitiater initiater (hereinafter also referred to as " and (C) into
Point ".).As Photoepolymerizationinitiater initiater, it is not particularly limited, such as acylphosphine oxide system Photoepolymerizationinitiater initiater, alkylbenzene can be used
Ketone system Photoepolymerizationinitiater initiater, intramolecular hydrogen capture the arbitrary Photoepolymerizationinitiater initiater such as type Photoepolymerizationinitiater initiater, wherein, from reaction
Property, solidification uniformity from the viewpoint of, preferred acylphosphine oxide system Photoepolymerizationinitiater initiater.Specifically, 2,4,6- can be enumerated
Trimethyl benzoyl diphenyl base phosphine oxide, 2,2- dimethoxy -1,2- diphenylethane -1- ketone, phenylglyoxalates methyl esters
(phenyl glyoxylic acid methyl ester) etc., wherein, from the sight of free radical generation efficiency height, deep curability
Point consideration, preferably TMDPO.
Relative to (A) composition of 100 mass parts, the content of (C) composition is more than 0.5 mass parts preferably 1.0 mass parts
More than, more preferably more than 1.5 mass parts.If the content of (C) Photoepolymerizationinitiater initiater is above range, solidification reactivity be present
Become the trend of good reproducibility, long-term reliability raising.As the upper limit of the content of (C) composition, it is not particularly limited, but
If crossing the trend that optical characteristics reduction at most be present, so preferably below 7.0 mass parts.
[(D) silane coupler]
The UV curable resin compositions of present embodiment also include (D) in addition to comprising above-mentioned (A)~(C) compositions
Silane coupler is (hereinafter also referred to as " (D) composition ".).As described above, the UV curable resin compositions of present embodiment pass through
Comprising UV curing type polyfunctional monomers, so as to improve the viscoplasticity under normal temperature so that LCD regeneration can be carried out.On the other hand,
In the case of viscoplasticity height, the trend reduced with the cementability of adherend be present.In present embodiment, by making UV curing types
Contain silane coupler in resin combination, so as to maintain bonding force, and improve the situation that especially adherend is glass plate
Under long-term reliability.
As (D) composition, it is not particularly limited, such as haplotype silane coupler, alkoxy oligomeric silicon can be used
The arbitrary silane couplers such as alkane coupling agent, multifunctional type silane coupler.Wherein, from the situation that raising adherend is glass
Under cementability, keep long-term reliability such from the viewpoint of, it is silane coupled preferably with (methyl) acrylic acid series group
Agent, more preferably 3- acryloxypropyls trimethoxy silane.
Relative to (A) composition of 100 mass parts, the content of (D) composition is 0.1~5 mass parts, preferably 0.5~3.0 matter
Measure part, more preferably 0.5~1.5 mass parts.If the content of (D) composition is above range, long-term reliability and regeneration be present
The harmony of property becomes good trend.
[other compositions]
, can be with the UV curable resin compositions of present embodiment in addition to comprising above-mentioned (A)~(D) compositions
Include the various fillers such as silica, aluminum oxide, hydrated alumina；It is antioxidant, ultra-violet absorber, light stabilizer, anti-quiet
Electric agent, levelling agent (leveling agent), defoamer, coloring pigment, organic solvent etc. would generally be added in bonding agent
Additive.
[adhesive sheet]
Adhesive sheet in present embodiment includes above-mentioned UV curable resin compositions.Specifically, for example, passing through
Coating resin composition and make its drying on the diaphragms such as PET, diaphragm is then also provided with opposite face, so as to
To the adhesive sheet that diaphragm is provided with two sides.It is particularly preferred that using organic solvent by UV curable resin compositions
Varnish is made, is then coated on diaphragm, is dried.As now used organic solvent, it is not particularly limited, example
Toluene, methyl ethyl ketone, cyclohexanone, propylene glycol monomethyl ether, dimethyl acetamide can such as be enumerated.Wherein, from deliquescent sight
Point consideration, preferably methyl ethyl ketone.In addition, relative to (A) composition of 100 mass parts, the content of the organic solvent in varnish is excellent
Elect 30~90 mass parts, more preferably 40~70 mass parts as.
As diaphragm, it is not particularly limited, such as can enumerates by selected from by polyethylene terephthalate, poly- naphthalene two
The film that more than a kind of resin in the group of formic acid glycol ester and polybutylene terephthalate (PBT) composition is formed, wherein, from
From the viewpoint of reducing manufacturing cost, the film that is preferably formed by pet resin.
For diaphragm, demoulding processing can be implemented to the face of coating resin composition.It is de- by implementing to diaphragm
Mould processing, so as to easily peel off diaphragm when in use, therefore operability improves.Handled as the demoulding, without special
Limit, such as the releasing agent such as usable silicon-type releasing agent, fluorine system releasing agent, chain alkyl graft polymers system releasing agent,
Or method being surface-treated using corona treatment etc..
, can be suitably using funny according to coating thickness as the method for the coating UV curable resin composition on diaphragm
Number coating machine (comma coater), die coating machine (die coater), gravure coater (gravure coater) etc..
For drying for UV curable resin compositions, online drying machine (in-line dryer) etc. can be used
Implement, drying condition now can suitably be adjusted according to the species of each composition and amount etc..Dried adhesive sheet
Thickness is preferably 10~250 μm, more preferably 25~125 μm, more preferably 30~75 μm.If the thickness of adhesive sheet is
Above range, then cementability become good, long-term reliability improve.In present embodiment, so-called long-term reliability, specifically
Include following situations：The cementability of LCD and pattern polarizer becomes good, so be not likely to produce dislocation, as a result observer's energy
Enough it was observed that good 3D images.And then if the thickness of adhesive sheet is above range, between LCD and pattern polarizer
Distance become suitable, watch 3D images when, it can be ensured that the appropriate angle of visual field.
[3D liquid crystal panels]
LCD and pattern polarizer are laminated by the 3D liquid crystal panels in present embodiment, the LCD with it is described
Polarizer is bonded using the adhesive sheet in present embodiment.3D liquid crystal panels can for example be obtained by following manner
Arrive：Adhesive sheet is bonded on polarizer, is then bonded LCD from the upper side, further, makes adhesive sheet by irradiating UV
Material carries out UV solidifications.
As pattern polarizer, it can be used and form figuratum glass plate.
It should be noted that the UV curable resin compositions of present embodiment cannot be only used for the use of 3D liquid crystal panels
On the way, and available for imagination all purposes regenerated the display devices such as LCD, organic EL.As such purposes, example
Touch sensor panel, digital signage (digital signage) can such as be enumerated.
Embodiment
Hereinafter, the present invention is further specifically described using embodiment and comparative example, but the present invention is not limited in these
Embodiment.
Each composite material used in embodiment and comparative example is as described below.
[(A) composition：UV curing types prepolymer]
According to following synthesis example 1~3 and compare synthesis example 1 to make UV curing type prepolymers (a)~(d).
[(B) composition：UV curing types polyfunctional monomer]
(1) UV curing type polyfunctional monomers (a)
Dipentaerythritol acrylate
Daicel-Allnex Ltd. systems, product name " DPHA "
(2) UV curing type polyfunctional monomers (b)
Tricyclodecane Dimethanol diacrylate
Daicel-Allnex Ltd. systems, product name " IRR214-K "
(3) UV curing type polyfunctional monomers (c)
Trimethylolpropane trimethacrylate
Daicel-Allnex Ltd. systems, product name " TMPTA "
(4) UV curing type polyfunctional monomers (d)
Ethoxylation phenyl acrylate (simple function)
Daicel-Allnex Ltd. systems, product name " EBECRYL110 "
[(C) composition：Photoepolymerizationinitiater initiater]
(1) Photoepolymerizationinitiater initiater (a)
2,4,6- trimethyl benzoyl diphenyl base phosphine oxides
BASF AG's system, trade name " Irgacure TPO ", acylphosphine oxide system Photoepolymerizationinitiater initiater
(2) Photoepolymerizationinitiater initiater (b)
2,2- dimethoxy -1,2- diphenylethane -1- ketone
BASF AG's system, trade name " Irgacure 651 ", alkyl phenones system Photoepolymerizationinitiater initiater
(3) Photoepolymerizationinitiater initiater (c)
Phenylglyoxalates methyl esters
BASF AG's system, " Irgacure MBF ", intramolecular hydrogen capture type Photoepolymerizationinitiater initiater to trade name
[(D) composition：Silane coupler]
(1) silane coupler (a)
Haplotype silane coupler
Chemical industrial company of SHIN-ETSU HANTOTAI system, trade name " KBM-5103 ", 3- acryloxypropyl trimethoxy silanes
(2) silane coupler (b)
Alkoxy oligomeric silane coupler
Chemical industrial company of SHIN-ETSU HANTOTAI system, trade name " KR-513 "
(3) silane coupler (c)
Multifunctional type silane coupler
Chemical industrial company of SHIN-ETSU HANTOTAI system, trade name " X-12-1050 "
Each evaluation method and assay method are as described below.
[reproducibility]
(1) sample making step
The PET film of the side of adhesive sheet is peeled off, is conformed on glass (0.7t, 19 inches), entered by lamination
Row hot pressing (autoclave) is handled.Lamination use roll lamination (roll laminate), using be laminated roll temperature as 25~40 DEG C,
The condition that laminating roll line pressure is 1.0~2.0kgf/cm, lamination roller speed is 0.3~2.0m/min is implemented；Hot pressing is using temperature as 60
DEG C, pressure 0.6MPa, time be 10min condition implement.The PET film of opposite side is peeled off, by vacuum lamination by its with
LCD is bonded, and is carried out hot-pressing processing again, is then obtained test specimen by carrying out UV exposures.Vacuum lamination is using temperature as 25
~50 DEG C, pressure be 0.01~0.05MPa, vacuumize 60s, pressurize 30s condition implement.Hot pressing is using temperature as 60 DEG C, pressure
The condition for being 1hr for 0.6MPa, time is implemented.UV exposures use ultra high pressure mercury lamp source, to cause accumulated light to turn into
3000mJ/cm2Mode implement.
(2) assay method
After test specimen is placed into more than 24hr at normal temperatures, to having peeled off the adherend (glass, LCD) after glass
Breakage is observed, and is evaluated according to following standard.
◎：Do not make adherend damaged, can easily be regenerated
○：Do not make adherend damaged, can be regenerated
×：It is difficult to regenerate
[cementability]
(1) sample making step
Test specimen is made using the step same with reproducibility.
(2) assay method
Test specimen is positioned in damp and hot device with the state erect.Condition is temperature 50 C, humidity 80%, time
240hr.Then, in room temperature 24hr.For with start to be placed into compared with when in damp and hot device in the case of glass gluing
The dislocation of position, the presence or absence of float, foam and being observed, being evaluated according to following standard.
○：The dislocation of glass is not produced, floats, foam
×：The dislocation of glass is generated, floats, foam
[stickiness]
(1) sample making step
Test specimen is made using the step same with reproducibility.
(2) assay method
The display of test specimen is lighted, evaluated according to following standard.
○：Without generation fitting inequality, 3D dislocation (without the generation of double image) in display image
×：Fitting inequality, 3D dislocation (generation for having double image) are generated in display image
[optical characteristics]
(1) sample making step
The PET film of the side of adhesive sheet is peeled off, optical glass (40mm square) is conformed to by vacuum lamination
On.Vacuum lamination by 25~50 DEG C, pressure of temperature is 0.01~0.05MPa, vacuumize 10s, pressurization 10s condition is implemented.
The PET film of opposite side is peeled off, fitted in using the condition identical condition with above-mentioned vacuum lamination on optical glass, so
After carry out hot-pressing processing, then, test specimen is obtained by carrying out UV exposures.Hot pressing is by 60 DEG C, pressure of temperature
0.6MPa, the condition that the time is 1hr are implemented.UV exposures use ultra high pressure mercury lamp source, to cause accumulated light to turn into 3000mJ/
cm2Mode implement.
Using spectrophotometer (Hitachi High-Technologies Corporation U-4100) to test sample
The yellow colour index (YI) of product is measured.Condition determination is：Illuminant-C, transmission, wavelength X=380~760nm.
◎：YI values are less than 1.5
○：YI values are 1.5 less than 2
×：YI values are more than 2
(synthesis example 1) UV curing type prepolymers (a)
Using the four-necked bottle for possessing thermometer, condenser pipe, agitating device, it is sub- that 33.3 mass parts six are added into reaction vessel
Methyl diisocyanate (TOSOH CORPORATION systems, the name of an article：HDI, referred to as：HDI), 59.4 mass parts weight average molecular weight are
400 PCDL, 7.3 mass parts dimethylolpropionic acids, the dibutyl tin laurate as catalyst of 1 mass parts
The methyl ethyl ketone as organic solvent of organo-tin compounds such as (dibutyl tin laurate) and 100 mass parts, in
70 DEG C make it react 24 hours.
In order to confirm the response situation of obtained synthetic, analyzed using IR determining instruments.Confirm in IR figures
NCO characteristic absorptions (the 2270cm of the synthetic-1) disappear, and confirm that synthetic is the urethane acrylates with carboxyl
Ester.
Next, added into reaction vessel the urethane acrylate with carboxyl that 100 mass parts obtain,
7.1 mass parts GMAs, 0.7 mass parts as the triethylamine of catalyst and the work of 0.05 mass parts
For the quinhydrones of inhibitor of polymerization, carry out reacting for 12 hours in 75 DEG C, it is carried out addition reaction, thus obtain UV curing type pre-polymerizations
Thing (a).
It should be noted that make addition in the acid number measured as follows as below 5mgKOH/g time point
Reaction terminates.In addition, the weight average molecular weight of obtained UV curing type prepolymers (a) is 50,000, solid component concentration is 50 matter
% is measured, double bond equivalent is that 2,000g/eq, Tg is 5 DEG C.
(acid value measuring method)
The solid state component 1g of resin is weighed, adds mixed solvent (mass ratio：Toluene and methanol=50/50), after dissolving, add
Appropriate phenolphthalein solution is added to be titrated with 0.1N potassium hydroxide aqueous solution as indicator, acid is determined using following formula (α)
Value.
X=10 × Vf × 56.1/ (Wp × I) ... (α)
(in formula (α), x represents acid number (mgKOH/g), and Vf represents the titer (mL) of the 0.1N KOH aqueous solution, and Wp is represented
The quality (g) of the resin solution of measure, I represent the ratio (quality %) of the nonvolatile component in the resin solution of measure.)
(synthesis example 2) UV curing type prepolymers (b)
PCDL is replaced using PTMEG, in addition, UV is obtained using the method same with synthesis example 1 and consolidates
Change type prepolymer (b).
(synthesis example 3) UV curing type prepolymers (c)
PCDL is replaced using polyester-diol, in addition, UV is obtained using the method same with synthesis example 1 and consolidates
Change type prepolymer (c).
(comparing synthesis example 1) UV curing type prepolymers (d)
Load 100.0g conduct into the reaction vessel for possessing mixer, thermometer, dropping funel and nitrogen ingress pipe
The methoxypropanol (propylene glycol monomethyl ether (PGM)) of polymer solvent, is warming up to 80 degree while being stirred under nitrogen flowing.From
Following substances were added dropwise in above-mentioned reaction vessel by dropping funel through 3 hours with being incubated for 80 DEG C of state, and the material is：
The 13.5 mass parts styrene that are mixed in advance prior to room temperature, 67 mass parts ethyl acrylates, 11.5 mass parts acrylic acid and
The 0.5g azodiisobutyronitrile as radical polymerization initiator.It is same what is be stirred to reaction solution after completion of dropwise addition
When be warming up to 90 DEG C, while the temperature of reaction solution is remained into 90 degree further stirring 2 hours, so as to be copolymerized
Thing.
Next, copolymer, the 7.8 mass parts Glycidyl methacrylates that 100 mass parts obtain are added into reaction vessel
Glyceride, 0.8 mass parts as the triethylamine of catalyst and the quinhydrones as inhibitor of polymerization of 0.05 mass parts, in 100
DEG C carry out 12 hours react, make its carry out addition reaction, thus obtain UV curing type prepolymers (d).
It should be noted that terminate addition reaction in acid number as below 5mgKOH/g time point.In addition, obtain
The weight average molecular weight of UV curing type prepolymers (d) is 45,000, and solid component concentration is that 47 mass %, Tg are 3 DEG C.
(embodiment 1)
(1) preparation of UV curable resin compositions
100 mass parts UV curing type prepolymers (a) are added into reaction vessel, and then it is more to add 25 mass parts UV curing types
Functional monomer (a), 1.5 mass parts Photoepolymerizationinitiater initiaters (a), 1 mass parts silane coupler (a) and 140 mass parts are as solvent
Methyl ethyl ketone, be stirred, so as to obtain resin combination.
(2) making of adhesive sheet
The resin combination that will be obtained in above-mentioned (1), it is coated with a manner of causing dried thickness to turn into more than 30 μm
In in 38 μm of PET film, making it dry in 130 DEG C 5 minutes, PET film then is also provided with opposite face, obtains having on two sides
The adhesive sheet of PET film.
The evaluation of reproducibility, cementability, stickiness, optical characteristics is carried out using obtained adhesive sheet.
(embodiment 2~20), (comparative example 1~7)
The species and content of each composition of change as described in table 1~3, in addition, using similarly to Example 1
Method obtain UV curable resin compositions and adhesive sheet.
The evaluation of reproducibility, cementability, stickiness, optical characteristics is carried out using obtained adhesive sheet.
[table 1]
| Implement Example 1 | Implement Example 2 | Implement Example 3 | Implement Example 4 | Implement Example 5 | Implement Example 6 | Implement Example 7 | Implement Example 8 | Implement Example 9 | |
| UV curing type prepolymers (a) | 100 | 100 | 100 | 100 | 100 | 100 | 100 | ||
| UV curing type prepolymers (b) | 100 | ||||||||
| UV curing type prepolymers (c) | 100 | ||||||||
| The multifunctional list of UV curing types Body (a) | 25 | 25 | 25 | 60 | 15 | 25 | 25 | 25 | 25 |
| Photoepolymerizationinitiater initiater (a) | 1.5 | 1.5 | 1.5 | 1.5 | 1.5 | 0.5 | 5 | 1.5 | 1.5 |
| Silane coupler (a) | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 0.1 | 5 |
| Reproducibility | ◎ | ◎ | ◎ | ◎ | ○ | ○ | ◎ | ◎ | ○ |
| Cementability | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ |
| Stickiness | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ |
| Optical characteristics | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ○ | ◎ | ◎ |
[table 2]
[table 3]
| Comparative example 1 | Comparative example 2 | Comparative example 3 | Comparative example 4 | Comparative example 5 | Comparative example 6 | Comparative example 7 | |
| UV curing type prepolymers (a) | 100 | 100 | 100 | 100 | 100 | 100 | |
| UV curing type prepolymers (d) | 100 | ||||||
| UV curing type polyfunctional monomers (a) | 70 | 10 | 25 | 25 | 25 | 25 | |
| UV curing type polyfunctional monomers (d) | 25 | ||||||
| Photoepolymerizationinitiater initiater (a) | 1.5 | 1.5 | 0.2 | 1.5 | 1.5 | 1.5 | 1.5 |
| Photoepolymerizationinitiater initiater (b) | |||||||
| Photoepolymerizationinitiater initiater (c) | |||||||
| Silane coupler (a) | 1 | 1 | 1 | 7 | 1 | 1 | |
| Reproducibility | ○ | × | × | ◎ | × | ○ | × |
| Cementability | × | ○ | × | × | ○ | × | ○ |
| Stickiness | × | ○ | ○ | ○ | ○ | ○ | ○ |
| Optical characteristics | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ |
Industrial applicability
The adhesive sheet of UV curable resin compositions comprising the present invention industrially has as liquid crystal display etc.
Bonding agent utilizability.
Claims (11)
1.UV curable resin compositions, it is solid that the UV curable resin compositions contain (A) UV curing types prepolymer, (B) UV
Change type polyfunctional monomer, (C) Photoepolymerizationinitiater initiater and (D) silane coupler,
(A) composition is carbamate (methyl) acrylate,
Relative to (A) composition described in 100 mass parts, the content of (B) composition is 15~60 mass parts, (C) composition
Content for more than 0.5 mass parts, the content of (D) composition is 0.1~5 mass parts.
2. UV curable resin compositions as claimed in claim 1, wherein, carbamate (methyl) acrylate is
Selected from by carbamate (methyl) acrylate with polycarbonate backbone, the carbamate (first with polyether skeleton
Base) acrylate and with polyester backbone carbamate (methyl) acrylate form group in more than a kind.
3. UV curable resin compositions as claimed in claim 1 or 2, wherein, carbamate (methyl) acrylic acid
The weight average molecular weight of ester is 10,000~100,000, and double bond equivalent is 1,000~5,000g/eq.
4. UV curable resin compositions as claimed in claim 1 or 2, wherein, (B) the UV curing type polyfunctional monomers are
(methyl) acrylic monomer with the functional groups of more than 2.
5. UV curable resin compositions as claimed in claim 1 or 2, wherein, (C) Photoepolymerizationinitiater initiater is acyl group oxygen
Change phosphine system Photoepolymerizationinitiater initiater.
6. UV curable resin compositions as claimed in claim 5, wherein, acylphosphine oxide system Photoepolymerizationinitiater initiater is
2,4,6- trimethyl benzoyl diphenyl base phosphine oxides.
7. UV curable resin compositions as claimed in claim 1 or 2, wherein, (D) silane coupler is with (first
Base) acrylic acid series group silane coupler.
8. adhesive sheet, the adhesive sheet includes UV curable resin compositions according to any one of claims 1 to 7.
9. adhesive sheet as claimed in claim 8, the dried thickness of the adhesive sheet is 10~250 μm.
10.3D liquid crystal panels, it is the 3D liquid crystal panels for being laminated LCD and pattern polarizer, wherein,
It is using the adhesive sheet described in claim 8 or 9 that the LCD is Nian Jie with the polarizer.
11. 3D liquid crystal panels as claimed in claim 10, wherein, the pattern polarizer is to form figuratum glass
Plate.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016-158145 | 2016-08-10 | ||
| JP2016158145A JP6502295B2 (en) | 2016-08-10 | 2016-08-10 | UV curable resin composition |
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| Publication Number | Publication Date |
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| CN107722916A true CN107722916A (en) | 2018-02-23 |
| CN107722916B CN107722916B (en) | 2021-06-04 |
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| CN201710576642.XA Active CN107722916B (en) | 2016-08-10 | 2017-07-14 | UV-curable resin composition |
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| JP (1) | JP6502295B2 (en) |
| KR (1) | KR102393003B1 (en) |
| CN (1) | CN107722916B (en) |
| TW (1) | TWI679262B (en) |
Cited By (1)
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|---|---|---|---|---|
| CN114391026A (en) * | 2019-09-19 | 2022-04-22 | 汉高股份有限及两合公司 | Photocurable (meth)acrylate compositions |
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|---|---|---|---|---|
| JP6704013B2 (en) * | 2017-06-01 | 2020-06-03 | 株式会社有沢製作所 | Double-sided adhesive sheet, 3D liquid crystal panel and manufacturing method thereof |
| JP2020019141A (en) * | 2018-07-30 | 2020-02-06 | 凸版印刷株式会社 | Barrier film, wavelength conversion sheet, and method for manufacturing wavelength conversion sheet |
| JP7214302B2 (en) * | 2018-12-28 | 2023-01-30 | フジコピアン株式会社 | thin support adhesive film |
| JP7214303B2 (en) * | 2018-12-28 | 2023-01-30 | フジコピアン株式会社 | thin support adhesive film |
| CN114341290A (en) * | 2019-10-01 | 2022-04-12 | 三菱化学株式会社 | Adhesive polarizing laminated film, adhesive sheet, laminated member, and image display device |
| JP7563081B2 (en) | 2019-10-01 | 2024-10-08 | 三菱ケミカル株式会社 | POLARIZING FILM WITH ADHESIVE LAYER, ADHESIVE SHEET, LAMINATED MEMBER, AND IMAGE DISPLAY DEVICE |
| CN113667445B (en) | 2020-05-14 | 2024-09-10 | 三键有限公司 | Photocurable composition |
| JP2022047865A (en) * | 2020-09-14 | 2022-03-25 | 株式会社飯沼ゲージ製作所 | Work bonding device and work bonding method |
| CN113372824B (en) * | 2021-06-24 | 2023-03-14 | 苏州赛伍应用技术股份有限公司 | Water-impact-resistant high-viscosity UV (ultraviolet) viscosity-reducing adhesive and preparation method and application thereof |
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| TW201811946A (en) | 2018-04-01 |
| CN107722916B (en) | 2021-06-04 |
| TWI679262B (en) | 2019-12-11 |
| JP2018024785A (en) | 2018-02-15 |
| JP6502295B2 (en) | 2019-04-17 |
| KR102393003B1 (en) | 2022-05-02 |
| KR20180018316A (en) | 2018-02-21 |
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