CN101805422A - Optical lens energy ray curable resin composition and cured article thereof - Google Patents
Optical lens energy ray curable resin composition and cured article thereof Download PDFInfo
- Publication number
- CN101805422A CN101805422A CN201010119224A CN201010119224A CN101805422A CN 101805422 A CN101805422 A CN 101805422A CN 201010119224 A CN201010119224 A CN 201010119224A CN 201010119224 A CN201010119224 A CN 201010119224A CN 101805422 A CN101805422 A CN 101805422A
- Authority
- CN
- China
- Prior art keywords
- methyl
- acrylate
- resin combination
- compound
- optical lens
- 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
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- 230000003287 optical effect Effects 0.000 title claims abstract description 20
- 239000011342 resin composition Substances 0.000 title claims abstract description 14
- 229920005989 resin Polymers 0.000 claims abstract description 67
- 239000011347 resin Substances 0.000 claims abstract description 67
- -1 acrylic ester Chemical class 0.000 claims abstract description 66
- 239000000178 monomer Substances 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 66
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 30
- 239000004593 Epoxy Substances 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 235000010292 orthophenyl phenol Nutrition 0.000 claims description 12
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical group CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 claims description 11
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims description 7
- 230000006978 adaptation Effects 0.000 abstract description 19
- 230000007704 transition Effects 0.000 abstract description 9
- 239000000463 material Substances 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 description 43
- 239000000203 mixture Substances 0.000 description 38
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
- 239000007795 chemical reaction product Substances 0.000 description 17
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 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 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 5
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- IPJWNWFUOHMNCS-UHFFFAOYSA-N C(C=C)(=O)OC.OC(CC)(C1=CC=CC=C1)O Chemical compound C(C=C)(=O)OC.OC(CC)(C1=CC=CC=C1)O IPJWNWFUOHMNCS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 229950011260 betanaphthol Drugs 0.000 description 4
- 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 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 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
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000723346 Cinnamomum camphora Species 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 238000004026 adhesive bonding Methods 0.000 description 3
- 229960000846 camphor Drugs 0.000 description 3
- 229930008380 camphor Natural products 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000007520 diprotic acids Chemical class 0.000 description 3
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 3
- 229940059574 pentaerithrityl Drugs 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- AKKQRBAJPYHABK-UHFFFAOYSA-N 1,1-diethoxyprop-1-ene Chemical compound CCOC(=CC)OCC AKKQRBAJPYHABK-UHFFFAOYSA-N 0.000 description 2
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- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
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- KIAMPLQEZAMORJ-UHFFFAOYSA-N 1-ethoxy-2-[2-(2-ethoxyethoxy)ethoxy]ethane Chemical compound CCOCCOCCOCCOCC KIAMPLQEZAMORJ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 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
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- XISFOXBYRQWDNK-UHFFFAOYSA-N 2-(2-methylphenyl)propan-2-amine;hydrochloride Chemical compound [Cl-].CC1=CC=CC=C1C(C)(C)[NH3+] XISFOXBYRQWDNK-UHFFFAOYSA-N 0.000 description 1
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-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
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-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
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-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
- 229940061334 2-phenylphenol Drugs 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-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
- DOFIAZGYBIBEGI-UHFFFAOYSA-N 3-sulfanylphenol Chemical compound OC1=CC=CC(S)=C1 DOFIAZGYBIBEGI-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- MKSQUONKTTUODA-UHFFFAOYSA-N C(C=C)(=O)O.C(C=C)(=O)O.OC(CC)(C1=CC=CC=C1)O Chemical compound C(C=C)(=O)O.C(C=C)(=O)O.OC(CC)(C1=CC=CC=C1)O MKSQUONKTTUODA-UHFFFAOYSA-N 0.000 description 1
- NGMNTLCQDNNBNT-UHFFFAOYSA-N C(C=C)(=O)OC.C(CS)(=O)OCCOC(CS)=O Chemical compound C(C=C)(=O)OC.C(CS)(=O)OCCOC(CS)=O NGMNTLCQDNNBNT-UHFFFAOYSA-N 0.000 description 1
- CCKUJGNTFZSJIN-UHFFFAOYSA-N C(C=C)(=O)OC.C1(=CC=CC=C1)C1=C(C=CC=C1)O Chemical compound C(C=C)(=O)OC.C1(=CC=CC=C1)C1=C(C=CC=C1)O CCKUJGNTFZSJIN-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 229920006311 Urethane elastomer Polymers 0.000 description 1
- VZTQQYMRXDUHDO-UHFFFAOYSA-N [2-hydroxy-3-[4-[2-[4-(2-hydroxy-3-prop-2-enoyloxypropoxy)phenyl]propan-2-yl]phenoxy]propyl] prop-2-enoate Chemical compound C=1C=C(OCC(O)COC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OCC(O)COC(=O)C=C)C=C1 VZTQQYMRXDUHDO-UHFFFAOYSA-N 0.000 description 1
- BEUGBYXJXMVRFO-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-phenylmethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=CC=C1 BEUGBYXJXMVRFO-UHFFFAOYSA-N 0.000 description 1
- YYQLNLDMILHCQP-UHFFFAOYSA-N [PH3]=O.C1=CC=CC=C1C1=CC=CC=C1 Chemical compound [PH3]=O.C1=CC=CC=C1C1=CC=CC=C1 YYQLNLDMILHCQP-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000012675 alcoholic extract Substances 0.000 description 1
- 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 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 150000008366 benzophenones Chemical class 0.000 description 1
- UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 description 1
- LRRJQNMXIDXNIM-UHFFFAOYSA-M benzyl(trimethyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)CC1=CC=CC=C1 LRRJQNMXIDXNIM-UHFFFAOYSA-M 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 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 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- RLFXWALMKAWBBF-UHFFFAOYSA-N methyl prop-2-enoate propane-1,2,3-triol Chemical compound C(C=C)(=O)OC.OCC(O)CO RLFXWALMKAWBBF-UHFFFAOYSA-N 0.000 description 1
- VFPJJGZRHMOKLJ-UHFFFAOYSA-N methyl(triphenyl)antimony Chemical compound C=1C=CC=CC=1[Sb](C=1C=CC=CC=1)(C)C1=CC=CC=C1 VFPJJGZRHMOKLJ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- BPYXFMVJXTUYRV-UHFFFAOYSA-J octanoate;zirconium(4+) Chemical compound [Zr+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O BPYXFMVJXTUYRV-UHFFFAOYSA-J 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 230000000176 photostabilization Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/08—Homopolymers or copolymers of acrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/185—Acids containing aromatic rings containing two or more aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present invention relates to optical lens energy ray curable resin composition and cured article thereof.The invention provides release property, mould circulation ratio,, high refractive index good, second-order transition temperature height and low viscous resin combination to the adaptation of base material.A kind of optical lens energy ray curable resin composition wherein, comprises: have the phenylate base mono acrylic ester monomer (A), general formula (1) (in the formula, R
1Identical or different, the alkyl of expression hydrogen atom or carbonatoms 1 to 4; R
2Identical or different, the alkyl of expression carbonatoms 1 to 4; M and n are average repeat number, m+n=0.4～12) expression compound (B) and Photoepolymerizationinitiater initiater (C).
Description
Technical field
The present invention relates to optical lens energy ray curable resin composition and cured article thereof.More specifically, the present invention relates to be particularly suitable for the resin combination and the cured article thereof of lens classes such as Fresnel Lenses, biconvex lens, prismatic lens, microlens.
Background technology
In the past, above-mentioned lens are shaped by impact molding, casting methods such as (casting methods).Therefore impact molding produces rate variance by a plurality of circulation manufacturings such as heating, pressurization, coolings.Casting is monomer to be injected mould carry out polymerization, so Production Time is long, and because the problem that needs a plurality of moulds thereby exist manufacturing cost to rise.In order to address these problems, various schemes (patent documentation 1, patent documentation 2) have been proposed about using ultra-violet solidified resin composition.
Obtained success to a certain extent by the method for using ultraviolet-curing resin composition to make the middle optical lens that use such as transmission screen.But there is the problem of the release property difference of peeling off with the adaptation difference of substrate with from mould in the cured article of these existing resin combinations.If adaptation is poor, then the kind of spendable substrate is limited, is difficult to obtain required optics rerum natura.If release property is poor, then resin residue is on mould during the demoulding, and mould becomes and can not use.In addition, also there are the following problems: provide the good cured article of adaptation resin combination since with the driving fit of mould might as well, so easy variation of release property, on the other hand, the easy variation of resin combination adaptation that release property is good.Therefore, be desirable to provide the resin combination that can satisfy these two kinds of performances of release property of peeling off with the adaptation of substrate with from mould.
The lens class composition that uses in the optical lens etc. along with the height of image in recent years becomes more meticulous with the slimming of finished product etc., requires the high resin combination of specific refractory power.In addition, in order to be processed into finer shape or to process thinlyyer or be processed as the sheet or the film of web-like continuously, the tendency of requirement low viscosity resin composition is arranged.In addition, microtexture such as also require when batching lens survivable.In addition, because the thermal conductance of light source etc. causes that lens shape changes also is fatal, at this moment, require second-order transition temperature (Tg) height when using as goods are actual.
Wherein, proposed to have concurrently the resin combination of adaptation, two kinds of performances of release property in patent documentation 3, still, the viscosity that is used to be processed as fine shape more is not talkative fully; (methyl) acrylate that discloses the use dinaphthol in patent documentation 4 is as the liquid crystal material, and still, purposes is limited to the liquid crystal material, for the clearly record of speciality of optics aspect.
No matter be which kind of situation, as all being difficult to have concurrently high refractive index, high Tg point, release property, adaptation and low viscosity with composition having high refractive index and have the lens class of using in the optical lens etc. of microtexture, thereby do not obtain to satisfy the lens class composition of all characteristics as yet.
Patent documentation 1: Japanese kokai publication sho 63-167301 communique
Patent documentation 2: Japanese kokai publication sho 63-199302 communique
Patent documentation 3: No. the 3209554th, Japanese Patent
Patent documentation 4: No. 2008/0090026 specification sheets of U.S. Patent Application Publication
Summary of the invention
The object of the present invention is to provide lens that be fit to make Fresnel Lenses, biconvex lens, prismatic lens, microlens etc. low viscosity resin composition and release property, mould circulation ratio, adaptation is good and the cured article of high refractive index.
The inventor has carried out research extensively and profoundly in order to address the above problem, and found that, ultra-violet solidified resin composition and cured article thereof with specific composition can address the above problem, and have finished the present invention.
That is, the present invention relates to and the following.
(1) a kind of optical lens energy ray curable resin composition wherein, comprises:
Have the mono acrylic ester monomer (A) of phenylate base, the compound (B) and the Photoepolymerizationinitiater initiater (C) of general formula (1) expression,
In the formula (1), R
1Identical or different, the alkyl of expression hydrogen atom or carbonatoms 1 to 4; R
2Identical or different, the alkyl of expression carbonatoms 1 to 4; M and n are average repeat number, m+n=0.4～12.
(2) above-mentioned (1) described resin combination, wherein, the mono acrylic ester monomer (A) with phenylate base is orthoxenol (many) oxyethyl group (methyl) acrylate, p-phenyl phenol (many) oxyethyl group (methyl) acrylate, orthoxenol epoxy (methyl) acrylate or p-phenyl phenol epoxy (methyl) acrylate.
(3), wherein, also comprise compound (B) (methyl) acrylic compound (D) in addition of mono acrylic ester monomer (A) with phenylate base and general formula (1) expression as above-mentioned (1) or (2) described resin combination.
(4) as each described resin combination in above-mentioned (1) to (3), wherein, (methyl) acrylic compound (D) is the compound with the structure that comprises the dihydroxyphenyl propane skeleton.
(5), wherein, be below the 3000mPas with the viscosity under 25 ℃ of E type viscometer determining as each described resin combination in above-mentioned (1) to (4).
(6) a kind of cured article obtains by each described resin combination in above-mentioned (1) to (5) is solidified, and the specific refractory power under 25 ℃ is more than 1.55.
(7) a kind of optical lens, the cured article described in its use above-mentioned (6).
The viscosity of resin combination of the present invention is low, the release property of its cured article, mould circulation ratio, good and specific refractory power is high with the adaptation of substrate.Therefore, be particularly suitable for the optical lens of Fresnel Lenses, biconvex lens, prismatic lens, microlens etc.
Embodiment
Resin combination of the present invention comprises the mono acrylic ester monomer (A) with phenylate base, the compound (B) and the Photoepolymerizationinitiater initiater (C) of general formula (1) expression.
The mono acrylic ester monomer (A) that uses among the present invention, have the phenylate base is described.
As the mono acrylic ester monomer (A) with phenylate base, can enumerate: (methyl) vinylformic acid phenoxy ethyl, phenyl (many) oxyethyl group (methyl) acrylate, (methyl) vinylformic acid are to cumyl phenoxy ethyl, (methyl) vinylformic acid tribromophenoxy ethyl ester, (methyl) vinylformic acid thiophenyl ethyl ester, (methyl) vinylformic acid-2-hydroxyl-3-phenoxy group propyl ester, phenylphenol (many) oxyethyl group (methyl) acrylate, phenylphenol epoxy (methyl) acrylate etc.Wherein, preferred phenylphenol (many) oxyethyl group (methyl) acrylate and phenylphenol epoxy (methyl) acrylate among the present invention, wherein, preferred orthoxenol (many) oxyethyl group (methyl) acrylate, p-phenyl phenol (many) oxyethyl group (methyl) acrylate, orthoxenol epoxy (methyl) acrylate and p-phenyl phenol epoxy (methyl) acrylate.
As phenylphenol (many) oxyethyl group (methyl) acrylate, the compound of the positive number of the repeat number average out to 1～3 of preferred oxyethyl group structure division can obtain by making to react with (methyl) vinylformic acid as the reaction product of the phenylphenol of raw material and oxyethane.Can use commercially available product (for example,, all can obtain) as the orthoxenol of ortho position body with as the p-phenyl phenol of contraposition body in the phenylphenol from Sanko Co., Ltd. as O-PP, P-PP.The reaction product of phenylphenol and oxyethane can obtain by known method, perhaps also can use commercially available product.By in the presence of stoppers such as esterifying catalysts such as tosic acid or sulfuric acid, Resorcinol or thiodiphenylamine, preferably (for example in solvent based, toluene, hexanaphthene, normal hexane, normal heptane etc.) existence under, the reaction product and the reaction of (methyl) vinylformic acid that preferably under 70～150 ℃, make phenylphenol and oxyethane, can obtain the many oxyethyl groups of phenylphenol (methyl) acrylate.(methyl) acrylic acid usage ratio is 1～5 mole, preferred 1.05～2 moles for 1 mole with respect to the reaction product of phenylphenol and oxyethane.Esterifying catalyst is 0.1～15 mole of %, preferred 1～6 mole of % with respect to (methyl) vinylformic acid that uses.
Phenylphenol epoxy (methyl) acrylate can make its resultant of reaction Resins, epoxy and (methyl) vinylformic acid react and obtain by make the reaction of above-mentioned phenylphenol and epihalohydrin in the presence of alkali metal hydroxide again.
As this epihalohydrin, can use Epicholorohydrin, Alpha-Methyl Epicholorohydrin, γ-methyl epichlorohydrin, epibromohydrin etc., the wherein preferred industrial Epicholorohydrin that obtains easily.
The usage quantity of epihalohydrin is generally 2～20 moles with respect to 1 mole of phenylphenol, preferred 3～15 moles.
As this alkali metal hydroxide, can enumerate sodium hydroxide, potassium hydroxide etc., can use solid substance, also can use its aqueous solution.When using the aqueous solution, can adopt following method: when adding to the aqueous solution of this alkali metal hydroxide in the reaction system continuously, under reduced pressure or water and epihalohydrin are distillated, carry out separatory again and remove and to anhydrate, and epihalohydrin is turned back in the reaction system.The usage quantity of alkali metal hydroxide is generally 0.1～10.0 mole with respect to 1 mole of above-mentioned phenylphenol, and preferred 0.3～5.0 mole, more preferably 0.8～3.0 mole.
In order to promote reaction, preferably add quaternary ammonium salts such as tetramethyl ammonium chloride, 4 bromide, trimethyl benzyl ammonia chloride as catalyzer.When using quaternary ammonium salt, its usage quantity is generally 0.1～20g for 1 mole with respect to above-mentioned phenylphenol, preferred 0.2～15g.
At this moment, carry out the aspect from reaction and consider, preferably add aprotic polar solvents such as aliphatic alcohols such as methyl alcohol, ethanol, Virahol, dimethyl sulfone, methyl-sulphoxide, tetrahydrofuran (THF), dioxane etc. and react.
Use pure time-like, its usage quantity is generally 1～50 quality %, preferred 2～30 quality % with respect to the usage quantity of epihalohydrin.In addition, when using aprotic polar solvent, be generally 3～100 quality %, preferred 5～80 quality % with respect to the usage quantity of epihalohydrin.
Temperature of reaction is generally 30～100 ℃, preferred 35～90 ℃.Reaction times is generally 0.2～10 hour, preferred 0.5～8 hour.In the presence of alkali metal hydroxide, with the reaction solution washing back of phenylphenol and epihalohydrin reaction or under the situation of not washing, under the heating decompression, remove epihalohydrin etc.In addition, in order to obtain the few Resins, epoxy of hydrolyzable halogen, the Resins, epoxy that obtains can be dissolved in toluene, the mibk equal solvent, and the aqueous solution that adds alkali metal hydroxides such as sodium hydroxide, potassium hydroxide reacts, thereby obtain the product of reliable closed loop.At this moment, the usage quantity of alkali metal hydroxide is generally 0.01～0.5 mole for 1 mole, preferred 0.05～0.3 mole with respect to the phenylphenol that uses.Temperature of reaction is generally 50～120 ℃, and the reaction times is generally 0.5～2 hour.
After reaction finishes, remove the salt of generation by filtrations, washing etc., distillation can obtain target Resins, epoxy thus except that desolvating etc. under the heating decompression again.By being the method for representative, can obtain need not to carry out the Resins, epoxy that special purifying just can use with such method.
Phenylphenol epoxy (methyl) acrylate obtains by making described Resins, epoxy and the reaction of (methyl) vinylformic acid.With respect to 1 epoxy equivalent (weight) of described Resins, epoxy, make preferred 0.8～1.1 equivalent, more preferably 0.9～1.05 normal (methyl) vinylformic acid reaction.
Reaction can be carried out under condition of no solvent, also can carry out in the independent or mixed organic solvents of the solvent that does not have alcoholic extract hydroxyl group as required, for example: ketones such as propyl alcohol, methylethylketone, hexalin; Arene such as benzene,toluene,xylene, tetramethyl-benzene; Glycol ethers such as glycol dimethyl ether, ethylene glycol diethyl ether, dipropylene glycol dme, dipropylene glycol diethyl ether, triethylene glycol dme, triethylene glycol diethyl ether; Ester classes such as ethyl acetate, butylacetate, methylcellosolve acetate, ethyl cellosolve acetate, butyl cellosolve acetate, Trivalin SF acetic ester, propylene glycol monomethyl ether monoacetate, pentanedioic acid dialkyl, Succinic Acid dialkyl, hexanodioic acid dialkyl; Cyclic ester classes such as gamma-butyrolactone; Oil series solvents such as sherwood oil, petroleum naphtha, hydrogenated naphtha, solvent naphtha; And the various monomers that comprise mono acrylic ester monomer described later (C) and (methyl) acrylic compound (D), for example: acryloyl morpholine, the terminal acrylate thing of the ethylene oxide adduct of 2-phenylphenol (for example, the OPP-1 that Nippon Kayaku K. K makes, OPP-2), polyoxyethylene glycol two (methyl) acrylate, tripropylene glycol two (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, the many oxyethyl groups three of TriMethylolPropane(TMP) (methyl) acrylate, the many propoxy-three of glycerine (methyl) acrylate, two (methyl) acrylate of the 6-caprolactone affixture of hydroxypivalic acid DOPCP (for example, KAYARAD HX-220 of Nippon Kayaku K. K's manufacturing, HX-620 etc.), tetramethylolmethane four (methyl) acrylate, many (methyl) acrylate of the reaction product of Dipentaerythritol and 6-caprolactone, Dipentaerythritol many (methyl) acrylate etc.
During reaction, in order to promote to react preferred use catalyzer, the usage quantity of this catalyzer is 0.1～10 quality % with respect to reaction product when using catalyzer.The temperature of reaction of this moment is 60～150 ℃, and in addition, the reaction times is preferably 5～60 hours.As the catalyzer that uses, for example can enumerate: triethylamine, benzyldimethylamine, triethyl ammonium chloride, benzyltrimethylammonium bromide, benzyltrimethylammonium iodide, triphenylphosphine, antimony triphenyl, methyl triphenyl antimony, sad chromium, zirconium caprylate etc.
In addition, can use the thermopolymerization hold back agent, as this thermopolymerization hold back agent, for example can enumerate: hydroquinone monomethyl ether, 2-methyl hydroquinone, Resorcinol, 2,6-ditertbutylparacresol, diphenylpicrylhydrazine, diphenylamine etc., when using the thermopolymerization hold back agent, preferably with respect to reactant to be the amount use of about 0.1 quality %～about 10 quality %.Suitably sampling in the reaction reaches moment below the 5mgKOH/g, below the preferred 3mgKOH/g as terminal point with the acid number of sample.
Below, compound (B) that use in the resin combination of the present invention, general formula (1) expression is described.
Compound of the present invention (B) can be by making 1,1 '-dinaphthol and oxirane or alkylene carbonate reaction, then in the presence of acid catalyst and (methyl) vinylformic acid carry out dehydration condensation and obtain.Among the present invention, as 1,1 '-dinaphthol, preferred (RS)-1 of using, 1 '-union-2-naphthol can be from S﹠amp; R CHIRAL CHEMICAL company etc. obtains.1, in the reaction of 1 '-dinaphthol and oxirane, with respect to 1 mole 1,1 '-dinaphthol makes 0.5～24 mole oxirane reaction.1, in the reaction of 1 '-dinaphthol and alkylene carbonate, with respect to 1 mole 1,1 '-dinaphthol makes 2～5 moles alkylene carbonate reaction.Oxirane or alkylene carbonate can be used alone, and also can two or more mixing use.
As the concrete example of oxirane, can enumerate: (carbonatoms 1～4) oxiranes such as oxyethane, propylene oxide, butylene oxide ring.In addition, as the concrete example of alkylene carbonate, can enumerate: carbonic acid (carbonatoms 1～4) alkylene carbonate such as ethylene carbonate, Texacar PC, butylene carbonate.
1, the reaction of 1 '-dinaphthol and oxirane or alkylene carbonate is under the basic catalysts such as sodium hydroxide, potassium hydroxide, carry out under the condition of 1～48 hour reaction times, 90～200 ℃ of temperature of reaction.1, in the reaction of 1 '-dinaphthol and oxirane,, use the basic catalyst of 0.01～5 quality % with respect to 100 quality % reaction mixtures.1, in the reaction of 1 '-dinaphthol and alkylene carbonate, with respect to 1 mole 1,1 '-dinaphthol uses 0.01～0.5 mole basic catalyst.
1, in the reaction product of 1 '-dinaphthol and oxirane or alkylene carbonate and (methyl) acrylic acid dehydration condensation, with respect to 1 mole 1,1 '-dinaphthol uses (methyl) vinylformic acid of 0.1～10 mole.As the reaction solvent in the dehydration condensation, can use the azeotropic solvent that the water distillation that generates in the reaction can be removed.At this, so-called azeotropic solvent is meant the boiling point with 60～130 ℃, can be easily and the solvent of water sepn, and especially preferably use a kind of of non-reacted organic solvents such as benzene, toluene, normal hexane, normal heptane, hexanaphthene or be use mixing two or more.Its usage quantity is arbitrarily, is 10～70 quality % with respect to reaction mixture preferably.
The reaction times of dehydration condensation can be in 1～24 hour scope, and temperature of reaction can be considered from shortening the poly-viewpoint of reaction times and resistance in 60～150 ℃ scope, preferably carried out under 75～120 ℃.
In commercially available product (methyl) vinylformic acid as the raw material use, add stoppers such as p methoxy phenol usually, can add stopper once more during reaction.As the example of such stopper, can enumerate: Resorcinol, p methoxy phenol, 2,4 dimethyl 6 tert butyl phenol, 3-hydroxythiophenol, para benzoquinone, 2,5-dihydroxyl para benzoquinone, thiodiphenylamine etc.Its usage quantity is 0.01～1 quality % with respect to reaction mixture.
The acid catalyst that uses in the dehydration condensation, can select arbitrarily from known acid catalysts such as sulfuric acid, methylsulfonic acid, trifluoromethanesulfonic acid, tosic acid, its usage quantity is 0.01～10 mole, preferred 1～5 mole of % with respect to 1 mole of (methyl) vinylformic acid.
The compound that uses in the resin combination of the present invention (B), if consider that specific refractory power reaches and the consistency of other composition, preferably with respect to 1 mole 1,1 '-dinaphthol makes 0.5～4 mole oxirane reaction and the compound that obtains or with respect to 1 mole 1, and 1 '-dinaphthol makes 2～4 moles alkylene carbonate reaction and the compound that obtains.As oxirane, then can be any one if methylene radical is 1～4 a oxirane, optimization ethylene oxide or propylene oxide.As alkylene carbonate, then can be any one if methylene radical is 1～4 a alkylene carbonate, preferred ethylene carbonate or Texacar PC.
In addition, except the compound (B) of the mono acrylic ester monomer (A) enumerated previously and general formula (1) expression with phenylate base, the hardness of the viscosity of the resin combination of the present invention that consideration obtains, adaptation, second-order transition temperature (Tg), cured article etc. can be used separately or composition (A), composition (B) (methyl) acrylic compound (D) are in addition used in two or more mixing.As this (methyl) acrylic compound (D), can enumerate (methyl) acrylate monomer or (methyl) origoester acrylate.
As (methyl) acrylate monomer, can enumerate above multifunctional (methyl) acrylate monomer of simple function (methyl) acrylate monomer, difunctionality (methyl) acrylate monomer, trifunctional etc.
As simple function (methyl) acrylate monomer, for example can enumerate: acryloyl morpholine, (methyl) vinylformic acid-2-hydroxy propyl ester, (methyl) vinylformic acid-4-hydroxyl butyl ester, hexanaphthene-1,4-dimethanol list (methyl) acrylate, (methyl) tetrahydrofurfuryl acrylate, (methyl) isobornyl acrylate, (methyl) vinylformic acid tribromophenoxy ethyl ester, (methyl) vinylformic acid dicyclo pentyl ester (dicyclopentanyl (meth) acrylate), (methyl) vinylformic acid double cyclopentenyl ester (dicyclopentenyl (meth) acrylate)), (methyl) vinylformic acid double cyclopentenyl oxygen ethyl ester (dicyclopentenyl oxyethyl (meth) acrylate)) etc.
As difunctionality (methyl) acrylate monomer, can enumerate: 1,4-butyleneglycol two (methyl) acrylate, 1,6-hexylene glycol two (methyl) acrylate, 1,9-nonanediol two (methyl) acrylate, tristane dimethanol two (methyl) acrylate, the many oxyethyl groups two of dihydroxyphenyl propane (methyl) acrylate, the many propoxy-two of dihydroxyphenyl propane (methyl) acrylate, the many oxyethyl groups two of Bisphenol F (methyl) acrylate, ethylene glycol bisthioglycolate (methyl) acrylate, polyoxyethylene glycol two (methyl) acrylate, two (methyl) acrylate of the 6-caprolactone affixture of hydroxypivalic acid DOPCP (for example, KAYARAD HX-220 of Nippon Kayaku K. K's manufacturing, HX-620 etc.).
As multifunctional (methyl) acrylate monomer more than the trifunctional, can enumerate: isocyanuric acid three (acrylyl oxy-ethyl) ester, tetramethylolmethane four (methyl) acrylate, Dipentaerythritol six (methyl) acrylate, Dipentaerythritol five (methyl) acrylate, tripentaerythritol six (methyl) acrylate, tripentaerythritol five (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, the many oxyethyl groups three of TriMethylolPropane(TMP) (methyl) acrylate, two (TriMethylolPropane(TMP)) four (methyl) acrylate etc.
As (methyl) origoester acrylate, can enumerate: carbamate (methyl) acrylate, epoxy (methyl) acrylate, polyester (methyl) acrylate etc.
As carbamate (methyl) acrylate, for example can enumerate: make diol compound (for example, ethylene glycol, Diethylene Glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1, the 4-butyleneglycol, neopentyl glycol, 1, the 6-hexylene glycol, 1, the 8-ethohexadiol, 1, the 9-nonanediol, the 2-methyl isophthalic acid, the 8-ethohexadiol, the 3-methyl isophthalic acid, the 5-pentanediol, 2,4-diethyl-1, the 5-pentanediol, 2-butyl-2-ethyl-1, ammediol, hexanaphthene-1, the 4-dimethanol, polyoxyethylene glycol, polypropylene glycol, many oxyethyl groups of dihydroxyphenyl propane glycol, many propoxy-of dihydroxyphenyl propane glycol etc.) or these diol compounds and diprotic acid or its acid anhydrides (for example, Succinic Acid, hexanodioic acid, nonane diacid, dimeracid, m-phthalic acid, terephthalic acid, phthalic acid or their acid anhydrides) the reaction product polyester glycol and organic multiple isocyanate (for example, 1,4-fourth vulcabond, 1, hexamethylene-diisocyanate, 2,2,4-trimethylammonium-hexamethylene diisocyanate, 2,4, chain stable hydrocarbon isocyanic ester such as 4-trimethylammonium-hexamethylene diisocyanate; Cyclic saturated hydrocarbon isocyanic ester such as isophorone diisocyanate, norbornene alkyl diisocyanate, dicyclohexyl methane diisocyanate, methylene-bis (4-cyclohexyl isocyanate), hydrogenated diphenyl methane diisocyanate, hydrogenated xylene diisocyanate, hydrogenated tolylene diisocyanate; 2,4-cresylene vulcabond, 1,3-xylylene diisocyanate, PPDI, 3,3 '-dimethyl diphenyl-4,4 '-vulcabond, 6-sec.-propyl-1,3-phenylene diisocyanate, 1, aromatic polyisocyanates such as 5-naphthalene diisocyanate) reaction, the reaction product that obtains with hydroxyl (methyl) acrylate addition then.In addition, can also enumerate described organic multiple isocyanate and hydroxyl (methyl) acrylate reactions and compound of obtaining etc.
As epoxy (methyl) acrylate, can enumerate: epoxy resins such as the terminal glycidyl group ether of the propylene oxide adduct of bisphenol A type epoxy resin, bisphenol f type epoxy resin, phenolic resin varnish type epoxy resin, dihydroxyphenyl propane, fluorenes Resins, epoxy and (methyl) acrylic acid reaction product etc.
As polyester (methyl) acrylate, for example can enumerate: the reaction product polyester glycol of above-mentioned diol compound and above-mentioned diprotic acid or its acid anhydrides and (methyl) acrylic acid reaction product etc.
Wherein, as (methyl) acrylic compound (D) that can in resin combination of the present invention, use, if the compound of considering specific refractory power then preferably having the structure that comprises the dihydroxyphenyl propane skeleton, for example, the many oxyethyl groups two of dihydroxyphenyl propane (methyl) acrylate, (methyl) acrylate monomers such as the many propoxy-two of dihydroxyphenyl propane (methyl) acrylate, carbamate (methyl) origoester acrylate (many oxyethyl groups of dihydroxyphenyl propane glycol with dihydroxyphenyl propane skeleton, diol compounds such as many propoxy-of dihydroxyphenyl propane glycol, the perhaps reaction product polyester glycol of these diol compounds and diprotic acid or its acid anhydrides, with organic multiple isocyanate and hydroxyl (methyl) acrylate reactions and the compound that obtains), epoxy (methyl) origoester acrylate (bisphenol A type epoxy resin with dihydroxyphenyl propane skeleton, epoxy resin such as the terminal glycidyl group ether of the propylene oxide adduct of dihydroxyphenyl propane and (methyl) acrylic acid reaction product etc.) be fit to.
In addition, if the adaptation of consideration cured article and viscosity etc., as (methyl) acrylic compound (D), simple function or difunctionality (methyl) acrylate monomer is fit to, wherein, preferred acryloyl morpholine, (methyl) tetrahydrofurfuryl acrylate, (methyl) vinylformic acid phenoxy ethyl, 1,4-butyleneglycol two (methyl) acrylate, 1,6-hexylene glycol two (methyl) acrylate, (methyl) isobornyl acrylate, (methyl) vinylformic acid dicyclo pentyl ester, (methyl) vinylformic acid double cyclopentenyl ester, (methyl) vinylformic acid double cyclopentenyl ethyl ester etc.
In addition, if consider the second-order transition temperature (Tg) of cured article, as (methyl) acrylic compound (D), above (methyl) acrylate monomers of trifunctional such as preferred isocyanuric acid three (acrylyl oxy-ethyl) ester, tetramethylolmethane four (methyl) acrylate, Dipentaerythritol six (methyl) acrylate, Dipentaerythritol five (methyl) acrylate, trimethylolpropane tris (methyl) acrylate.
As Photoepolymerizationinitiater initiater contained in the resin combination of the present invention (C), can enumerate: bitter almond oil camphor classes such as bitter almond oil camphor, benzoin methylether, ethoxybenzoin, bitter almond oil camphor propyl ether, benzoin iso-propylether; Methyl phenyl ketone, 2,2-dimethoxy-2-phenyl methyl phenyl ketone, 2,2-diethoxy-2-phenyl methyl phenyl ketone, 1,1-dichloroacetophenone, 2-hydroxy-2-methyl-phenyl-propane-1-ketone, diethoxy acetophenone, 1-hydroxycyclohexylphenylketone, 2-methyl isophthalic acid-[4-(methylthio group) phenyl]-2-morpholinyl propane-1-ketone, oligomeric [2-hydroxy-2-methyl-1-[4-(1-methyl ethylene) phenyl] acetone] etc. acetophenones; Anthraquinone classes such as 2-ethyl-anthraquinone, 2-tertiary butyl anthraquinone, 2-chloroanthraquinone, 2-amyl anthraquinone; 2, thioxanthene ketones such as 4-diethyl thioxanthone, 2-isopropyl thioxanthone, 2-clopenthixal ketone; Ketal classes such as methyl phenyl ketone dimethyl ketal, dibenzoyl dimethyl ketal; Benzophenone, 4-benzoyl-4 '-methyldiphenyl thioether, 4, benzophenones such as 4 '-dimethylamino benzophenone; 2,4,6-Three methyl Benzene formyl diphenyl phosphine oxide, two (2,4,6-Three methyl Benzene formyl)-phenylphosphine oxide, phenylbenzene-phosphine oxide classes such as (2,4,6-Three methyl Benzene formyl) phosphine oxide; Deng.Acetophenones be can preferably enumerate, 2-hydroxy-2-methyl phenyl-propane-1-ketone, 1-hydroxycyclohexylphenylketone further preferably enumerated.In addition, in the resin combination of the present invention, Photoepolymerizationinitiater initiater (C) can use separately, also can multiple mixing use, and preferably uses 2,4,6-Three methyl Benzene formyl diphenyl phosphine oxide, two (2,4,6-Three methyl Benzene formyl)-phenylphosphine oxide, phenylbenzene-(2,4,6-Three methyl Benzene formyl) at least a in the phosphine oxide class such as phosphine oxide.
The usage ratio of each composition of resin combination of the present invention can consider that required specific refractory power, second-order transition temperature, viscosity and adaptation wait to determine, with composition (A)+composition (B)+when composition (D) is set at 100 mass parts, the content of composition (A)+composition (B) is 50～100 mass parts, preferred especially 70～100 mass parts, therefore, the content of composition (D) is less than 50 mass parts, especially preferably less than 30 mass parts.In addition, when the total amount of composition (A)+composition (B) was set at 100 mass parts, the content of composition (A) was 10～95 mass parts wherein, preferred especially 20～90 mass parts.Composition (C) preferably uses 0.1～10 mass parts with respect to total amount 100 mass parts of composition (A)+composition (B)+composition (D), preferred especially 0.3～5 mass parts.
In the energy ray curable resin composition of the present invention, except that aforementioned composition, conveniences when operating in order to improve etc. can according to circumstances make up and contain releasing agent, defoamer, flow agent, photostabilizer, antioxidant, stopper, antistatic agent, UV light absorber etc.In addition, also can add polymer class such as acrylic polymers, polyester elastomer, urethane and nitrile rubber, inorganic or organic light diffusion filler etc. as required.Also can add solvent, but preferably not add solvent.
Resin combination of the present invention can be by preparing each composition mixed dissolution according to conventional methods.For example, can pass through in the round-bottomed flask with each composition input band whipping appts and thermometer, and obtain in 0.5～6 hour 40～80 ℃ of stirrings.
The viscosity of resin combination of the present invention, as viscosity that be fit to make the optical lens class, preferably use E type viscometer (TV-200: eastern machine industry corporate system) viscosity of Ce Dinging 25 ℃ times as 3000mPas below.
The cured article that can get by according to conventional methods resin combination irradiation ultraviolet radiation homenergic ray of the present invention being made its curing is also contained among the present invention.This cured article can followingly obtain: resin combination of the present invention is applied to has for example Fresnel Lenses, biconvex lens, on the pressing mold of the shape of prismatic lens etc. and the layer of this resin combination is set, gluing backboard as the hard transparent substrate (for example on this layer, comprise polymethacrylate resin, polycarbonate resin, polystyrene resin, the substrate or the film of the blend of vibrin or these polymkeric substance etc.), then, utilize irradiation ultraviolet radiation such as high voltage mercury lamp that this resin combination is solidified from this hard transparent substrate-side after, cured article is peeled off from this pressing mold.In addition, as the application of aforesaid method, also can be undertaken by the processing of continous way.
The optical lens of the optical lens part of the Fresnel Lenses of can obtain being formed with specific refractory power (25 ℃) like this and be more than 1.55, release property, mould circulation ratio, adaptation and photostabilization are good, biconvex lens, prismatic lens, microlens etc., these are also contained among the present invention.The ア タ of Co., Ltd. go system) in addition, specific refractory power can be passed through Abbe refractomecer (DR-M2: mensuration such as.
Resin combination of the present invention can be used for optical lens as mentioned above.As the purposes beyond the optical lens, can enumerate various coating agents, tackiness agent etc.
Embodiment
Below, illustrate in greater detail the present invention by embodiment.In addition, the present invention is not subjected to any restriction of following examples.
Synthesizing of compound (B)
Synthesis example 1
With 286.3g (1.0mol) (RS)-1,1 '-union-2-naphthol, 264.2g (3.0mol) ethylene carbonate, 41.5g (0.3mol) salt of wormwood and 2000ml toluene join have whipping appts, in the flask of return line and thermometer, and 110 ℃ of reactions 12 hours.
After the reaction, to the gained reaction solution wash, with the 1%NaOH solution washing, to wash until washing water then be neutral.Use the solvent distillation in the solution after rotatory evaporator under reduced pressure will be washed to remove, obtain 300.0g (RS)-1, the oxyethane 2mol reaction product of 1 '-union-2-naphthol.
Then, with 187.2g (0.5mol) (RS)-1, the oxyethane 2mol reaction product of 1 '-union-2-naphthol, 86.5g (2.4mol) vinylformic acid, 0.95g tosic acid, 0.87g Resorcinol, 917.4g toluene, 393.2g hexanaphthene join have whipping appts, in the flask of return line, thermometer and water trap, when under 95～105 ℃ temperature of reaction, reacting, water and solvent component distillation that reaction generates are removed.After the reaction, with in the 25%NaOH aqueous solution and after, with 200g 15 quality % salt solutions washing three times.Underpressure distillation removes desolvates, and obtains the resultant 337.8g shown in the following structural formula of faint yellow solid form.
The rerum natura of compound (B) is as follows.
Liquid refractivity (D line, 25 ℃) 1.62
1H-NMR(CDCl
3、300MHz)、ppm：
4.00-4.30ppm＝8H，5.60-5.90ppm＝4H，6.05-6.15ppm＝2H，7.05-7.50ppm＝8H，7.80-8.00ppm＝4H
Synthesizing of compound (D)
Synthesis example 2
139.3 parts of 2,4 toluene diisocyanates, 0.05 part of di-n-butyltin dilaurate and 0.16 part of p methoxy phenol are joined in the drying receptacle, be warming up to 40 ℃ and stirring.With 1 hour to wherein dripping 185.6 parts of 2-Hydroxy ethyl acrylates, confirm the heat production state simultaneously, 80 ℃ the reaction 1～2 hour.Reacted isocyanate value is below 0.1, and expression reaction basal ration is finished.
Obtain resin combination of the present invention and cured article according to the composition shown in following examples (numeric representation mass parts).In addition, as described below about the evaluation method and the judgement criteria of resin combination and cured film.
(1) viscosity: use E type viscometer (TV-200: Toki Sangyo Co., Ltd.'s system), measure down at 25 ℃.
(2) release property: expression solidified resin is the difficulty the during demoulding from mould.
Zero: the good demoulding from the mould
△: the demoulding is had any problem slightly or is peeled off sound during the demoulding
*: on demoulding difficulty or the mould residue is arranged
(3) mould circulation ratio: observe the surface shape of solidified uv curing resin layer and the surface shape of mould.
Zero: circulation ratio is good
*: circulation ratio is bad
(4) adaptation:
With resin combination be applied on the base material to thickness be about 50 μ m, use high voltage mercury lamp (80W/cm, ozone free) to carry out 1000mJ/cm then
2Irradiation, make the solidified test piece, carry out the adaptation evaluation according to JIS K5600-5-6.
Evaluation result be with 0～2 as zero, with 3～5 as *.
(5) specific refractory power (25 ℃): use Abbe refractomecer (DR-M2: the specific refractory power (25 ℃) of the ultraviolet curing resin layer after the ア タ of Co., Ltd. go system) mensuration is solidified.
(6) second-order transition temperature (Tg): use determination of viscoelasticity system (DMS-6000: Seiko Instruments Inc's system), at the Tg point of measuring the uv curing resin layer after solidifying under stretch mode, the frequency 1Hz.
Embodiment 1
Will be as 31 parts of orthoxenols, the one ethoxy propylene acid esters of composition (A), 20 parts of compounds that synthesis example 1 obtains as composition (B), 3 parts of 1-hydroxycyclohexylphenylketones as composition (C), 0.1 part phenylbenzene-(2,4,6-Three methyl Benzene formyl) phosphine oxide and as 20 parts of KAYARAD R-551 (Japanese chemical drug systems of composition (D), many oxyethyl groups of dihydroxyphenyl propane diacrylate), 4 parts of KAYARAD R-115 (Japanese chemical drug systems, bisphenol A epoxy acrylate), 18 part of three (2-acrylyl oxy-ethyl) isocyanic ester and 7 parts of acryloyl morpholines are heated to 60 ℃ and mixing, obtain resin combination of the present invention.The viscosity of this resin combination is 904mPas.In addition, by this resin combination being carried out 600mJ/cm with high voltage mercury lamp (80w/cm, ozone free)
2Irradiation make its curing and the specific refractory power (25 ℃) of the ultraviolet curing resin layer of the thickness 200 μ m that obtain is 1.587, second-order transition temperature (Tg) is 94 ℃.
And then, this resin combination is applied to make thickness on the prismatic lens mould be 50 μ m, gluing easy to be gluing PET film (it is thick that コ ス モ シ ヤ イ Application A4300,100 μ m spin in Japan), side high voltage mercury lamp radiation 1000mJ/cm from it more thereon as base material
2The ultraviolet ray of irradiation dose is peeled off after it is solidified, and obtains prismatic lens sheet of the present invention.
Evaluation result
Release property: zero; Mould circulation ratio: zero; Adaptation: zero
Embodiment 2
Use 52 parts of orthoxenol one ethoxy propylene acid esters as composition (A), use 3 parts of 2-hydroxy-2-methyl-1-phenyl-propane-1-ketone as composition (C), use compound, 13 parts of acryloyl morpholines and 5 parts of tetrahydrofurfuryl acrylates that 10 parts of synthesis examples 2 obtain as composition (D), obtain resin combination of the present invention in addition similarly to Example 1.The viscosity of this resin combination is 195mPas.In addition, operate similarly to Example 1 and the specific refractory power (25 ℃) of the resin layer that obtains is 1.597, second-order transition temperature (Tg) is 69 ℃.
Use the resin combination of gained to operate similarly to Example 1, obtain prismatic lens sheet of the present invention.
Evaluation result
Release property: zero; Mould circulation ratio: zero; Adaptation: zero
Comparative example 1
Embodiment 1 according to patent documentation 1 (Japanese kokai publication sho 63-167301), with 70 parts of ア ロ ニ Star Network ス M315 (isocyanuric acid three (2-acrylyl oxy-ethyl) ester), 30 parts of tetrahydrofurfuryl acrylates, be heated to 60 ℃ and mix, obtain the relatively resin combination of usefulness as 3 parts of 1-(4-the isopropyl phenyl)-2-hydroxy-2-methyl-2-propane-1-ketone of Photoepolymerizationinitiater initiater.The viscosity of this resin combination is 134mPas.In addition, operate similarly to Example 1 and the specific refractory power (25 ℃) of the resin layer that obtains is 1.52.
From this result as can be seen, the refractive index ratio of the composition of comparative example 1 composition of the present invention is low, is not suitable for making lens class of the present invention.
Comparative example 2
Embodiment 1 according to patent documentation 3 (No. the 3209554th, Japanese Patent), urethane acrylate (the polyester glycol of neopentyl glycol and hexanodioic acid of the synthesis example 1 of the synthetic document, ethylene glycol, the reaction product of cresylene vulcabond and 2-Hydroxy ethyl acrylate) and the compound of document synthesis example 3 (orthoxenol diethoxy propene acid esters), with 30 parts of above-mentioned urethane acrylates, 15 parts of above-mentioned orthoxenol diethoxy propene acid esters, 45 parts of KAYARAD R-551,10 portions of vinylformic acid tribromophenyls and 3 parts of イ Le ガ キ ュ ア one (1-hydroxycyclohexylphenylketones) are heated to 60 ℃ and mixing, obtain the relatively resin combination of usefulness.The viscosity of this resin combination is 4420mPas.In addition, operate similarly to Example 1 and the specific refractory power (25 ℃) of the resin layer that obtains is 1.574.
By this result as can be seen, the viscosity ratio of the composition of comparative example 2 combination object height of the present invention is not suitable for the continuous processing of the sheet or the film of fine processing or web-like.
From the evaluation result of embodiment 1,2, comparative example 1,2 as can be seen, resin combination viscosity of the present invention with specific composition is low, release property, mould circulation ratio and good to the adaptation of base material, and the specific refractory power height of its cured article and second-order transition temperature (Tg) height.Therefore, be suitable for having the optical lens of microtexture, for example Fresnel Lenses, biconvex lens, prismatic lens, microlens etc.The manufacturing that is particularly suitable for to carry out the purposes of microfabrication or comprises the operation that to process continuously.
Industrial applicability
Ultra-violet solidified resin composition of the present invention and solidfied material thereof mainly are particularly suitable for the optical lens of Fresnel Lenses, biconvex lens, prismatic lens, microlens etc.
Claims (7)
1. optical lens energy ray curable resin composition wherein, comprises:
Have the mono acrylic ester monomer (A) of phenylate base, the compound (B) and the Photoepolymerizationinitiater initiater (C) of general formula (1) expression,
In the formula (1), R
1Identical or different, the alkyl of expression hydrogen atom or carbonatoms 1 to 4; R
2Identical or different, the alkyl of expression carbonatoms 1 to 4; M and n are average repeat number, m+n=0.4～12.
2. resin combination as claimed in claim 1, wherein, the mono acrylic ester monomer (A) with phenylate base is orthoxenol (many) oxyethyl group (methyl) acrylate, p-phenyl phenol (many) oxyethyl group (methyl) acrylate, orthoxenol epoxy (methyl) acrylate or p-phenyl phenol epoxy (methyl) acrylate.
3. resin combination as claimed in claim 1 or 2 wherein, also comprises compound (B) (methyl) acrylic compound (D) in addition of mono acrylic ester monomer (A) with phenylate base and general formula (1) expression.
4. as each described resin combination in the claim 1 to 3, wherein, (methyl) acrylic compound (D) is the compound with the structure that comprises the dihydroxyphenyl propane skeleton.
5. as each described resin combination in the claim 1 to 4, wherein, be below the 3000mPas with the viscosity under 25 ℃ of E type viscometer determining.
6. cured article obtains by each described resin combination in the claim 1 to 5 is solidified, and the specific refractory power under 25 ℃ is more than 1.55.
7. optical lens, it uses the described cured article of claim 6.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009-034748 | 2009-02-18 | ||
| JP2009034748A JP5219084B2 (en) | 2009-02-18 | 2009-02-18 | Energy ray curable resin composition for optical lens sheet and cured product thereof |
Publications (2)
| Publication Number | Publication Date |
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| CN101805422A true CN101805422A (en) | 2010-08-18 |
| CN101805422B CN101805422B (en) | 2013-10-23 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2010101192246A Expired - Fee Related CN101805422B (en) | 2009-02-18 | 2010-02-12 | Energy ray-curable resin composition and cured product for optical lens sheet |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP5219084B2 (en) |
| KR (1) | KR101558338B1 (en) |
| CN (1) | CN101805422B (en) |
| TW (1) | TWI454492B (en) |
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| CN102898596A (en) * | 2011-07-27 | 2013-01-30 | 日本化药株式会社 | Energy ray gel-type resin composition used for optical lens, and condensate thereof and optical lens |
| CN103553971A (en) * | 2013-10-25 | 2014-02-05 | 张家港威迪森化学有限公司 | Preparation method for urethane acrylate |
| CN105579488A (en) * | 2013-09-26 | 2016-05-11 | 田冈化学工业株式会社 | Epoxy resin having binaphthalene skeleton |
| TWI558541B (en) * | 2015-04-02 | 2016-11-21 | 長興材料工業股份有限公司 | Photocurable lens and method of manufacturing the same |
| CN106662782A (en) * | 2014-07-17 | 2017-05-10 | 日本化药株式会社 | Liquid crystal sealing agent and liquid crystal display cell using same |
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| JP2013166900A (en) * | 2012-02-17 | 2013-08-29 | Nippon Kayaku Co Ltd | Energy beam curable resin composition for hard coat film, and hard coat film (1) |
| JP2013167837A (en) * | 2012-02-17 | 2013-08-29 | Nippon Kayaku Co Ltd | Energy beam curable resin composition for hard coat film, and hard coat film (2) |
| WO2013151001A1 (en) * | 2012-04-03 | 2013-10-10 | 東亞合成株式会社 | Active energy ray-curable composition, and metal base having cured film and method for producing same |
| JP6057409B2 (en) * | 2012-04-25 | 2017-01-11 | 日本化薬株式会社 | Energy ray curable resin composition for optical lens sheet and cured product thereof (1) |
| JP5974784B2 (en) * | 2012-09-28 | 2016-08-23 | Jnc株式会社 | Inkjet ink |
| JP6083900B2 (en) * | 2013-05-24 | 2017-02-22 | 田岡化学工業株式会社 | Method for producing binaphthalene compound |
| JP6083901B2 (en) * | 2013-05-24 | 2017-02-22 | 田岡化学工業株式会社 | Method for producing binaphthalene compound |
| WO2018051713A1 (en) | 2016-09-15 | 2018-03-22 | 富士フイルム株式会社 | Curable composition, cured material, optical member, lens, and compound |
| JP6635999B2 (en) * | 2017-10-13 | 2020-01-29 | 株式会社ダイセル | Method for producing potassium salt, and potassium salt |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1454933A (en) * | 2003-04-01 | 2003-11-12 | 四川大学 | Photocurable resin composition |
| WO2008105455A1 (en) * | 2007-02-28 | 2008-09-04 | Nippon Kayaku Kabushiki Kaisha | Energy ray-curable resin composition for optical lens sheet and cured product thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5986615A (en) * | 1982-11-11 | 1984-05-18 | Showa Denko Kk | Polymerizable composition |
| JP2807315B2 (en) * | 1990-06-28 | 1998-10-08 | 日本化薬株式会社 | (Meth) acrylic acid ester, resin composition containing the same, and cured product thereof |
| JP3209554B2 (en) * | 1991-12-19 | 2001-09-17 | 日本化薬株式会社 | Resin composition, ultraviolet curable resin composition for transmission screen and cured product thereof |
| JPH09272707A (en) * | 1996-04-04 | 1997-10-21 | Toagosei Co Ltd | Actinic-radiation-curing (meth)acrylate composition |
| CN1281975C (en) * | 2000-10-13 | 2006-10-25 | 日本清水产业株式会社 | Composition for optical material, optical material and plastic lens |
| JP4659288B2 (en) * | 2001-07-19 | 2011-03-30 | 独立行政法人産業技術総合研究所 | Composition for hologram recording material, hologram recording medium and method for producing the same |
| JP4802479B2 (en) * | 2004-02-18 | 2011-10-26 | Ｊｎｃ株式会社 | Polymerizable binaphthalene derivative |
| JP2005283632A (en) * | 2004-03-26 | 2005-10-13 | Fuji Photo Film Co Ltd | Polymerizable composition and negative image recording material |
| JP4433300B2 (en) * | 2005-01-05 | 2010-03-17 | 日本化薬株式会社 | Photosensitive resin composition and film having cured film thereof |
| JP5017938B2 (en) * | 2006-06-22 | 2012-09-05 | 川崎化成工業株式会社 | Photopolymerization sensitizer comprising bis (2- (meth) acryloxyalkoxy) naphthalene compound as an active ingredient, and use thereof |
| JP2008201972A (en) * | 2007-02-22 | 2008-09-04 | Kyocera Chemical Corp | Highly refractive material and optical transmission article using the same |
| WO2008136262A1 (en) | 2007-04-27 | 2008-11-13 | Nippon Kayaku Kabushiki Kaisha | (meth)acrylate compound, resin composition containing the same, cured product of the resin composition, and energy ray-curable resin composition for optical lens sheet and cured product thereof |
-
2009
- 2009-02-18 JP JP2009034748A patent/JP5219084B2/en not_active Expired - Fee Related
-
2010
- 2010-02-09 TW TW099103903A patent/TWI454492B/en not_active IP Right Cessation
- 2010-02-11 KR KR1020100013026A patent/KR101558338B1/en not_active IP Right Cessation
- 2010-02-12 CN CN2010101192246A patent/CN101805422B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1454933A (en) * | 2003-04-01 | 2003-11-12 | 四川大学 | Photocurable resin composition |
| WO2008105455A1 (en) * | 2007-02-28 | 2008-09-04 | Nippon Kayaku Kabushiki Kaisha | Energy ray-curable resin composition for optical lens sheet and cured product thereof |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102898596A (en) * | 2011-07-27 | 2013-01-30 | 日本化药株式会社 | Energy ray gel-type resin composition used for optical lens, and condensate thereof and optical lens |
| CN102898596B (en) * | 2011-07-27 | 2016-05-18 | 日本化药株式会社 | Energy ray curable resin composition and solidfied material and optical lens for optical lens |
| CN105579488A (en) * | 2013-09-26 | 2016-05-11 | 田冈化学工业株式会社 | Epoxy resin having binaphthalene skeleton |
| CN105579488B (en) * | 2013-09-26 | 2017-07-21 | 田冈化学工业株式会社 | Epoxy resin with dinaphthalene skeleton |
| CN103553971A (en) * | 2013-10-25 | 2014-02-05 | 张家港威迪森化学有限公司 | Preparation method for urethane acrylate |
| CN106662782A (en) * | 2014-07-17 | 2017-05-10 | 日本化药株式会社 | Liquid crystal sealing agent and liquid crystal display cell using same |
| CN106662782B (en) * | 2014-07-17 | 2019-07-26 | 日本化药株式会社 | Liquid crystal sealing agent and the liquid crystal display for using it |
| TWI558541B (en) * | 2015-04-02 | 2016-11-21 | 長興材料工業股份有限公司 | Photocurable lens and method of manufacturing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20100094369A (en) | 2010-08-26 |
| TWI454492B (en) | 2014-10-01 |
| JP5219084B2 (en) | 2013-06-26 |
| KR101558338B1 (en) | 2015-10-07 |
| CN101805422B (en) | 2013-10-23 |
| JP2010189534A (en) | 2010-09-02 |
| TW201035129A (en) | 2010-10-01 |
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