JP6320255B2 - Resin composition - Google Patents
Resin composition Download PDFInfo
- Publication number
- JP6320255B2 JP6320255B2 JP2014185932A JP2014185932A JP6320255B2 JP 6320255 B2 JP6320255 B2 JP 6320255B2 JP 2014185932 A JP2014185932 A JP 2014185932A JP 2014185932 A JP2014185932 A JP 2014185932A JP 6320255 B2 JP6320255 B2 JP 6320255B2
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acrylate
- compound
- resin composition
- diisocyanate
- 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.)
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- 239000011342 resin composition Substances 0.000 title claims description 82
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 200
- -1 acrylic compound Chemical class 0.000 claims description 142
- 150000001875 compounds Chemical class 0.000 claims description 94
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 229920005862 polyol Polymers 0.000 claims description 34
- 239000005062 Polybutadiene Substances 0.000 claims description 32
- 229920002857 polybutadiene Polymers 0.000 claims description 32
- 150000003077 polyols Chemical class 0.000 claims description 19
- 239000005056 polyisocyanate Substances 0.000 claims description 17
- 229920001228 polyisocyanate Polymers 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 229920005749 polyurethane resin Polymers 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 45
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 42
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 29
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 18
- 239000003822 epoxy resin Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 229920000647 polyepoxide Polymers 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 16
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000011521 glass Substances 0.000 description 14
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical group C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 13
- 229920002635 polyurethane Polymers 0.000 description 13
- 239000004814 polyurethane Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 239000010408 film Substances 0.000 description 12
- 239000000976 ink Substances 0.000 description 12
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 12
- 239000004593 Epoxy Substances 0.000 description 11
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 125000002723 alicyclic group Chemical group 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 9
- 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 9
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 9
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000853 adhesive Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 9
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 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 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 8
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 229920001451 polypropylene glycol Polymers 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 8
- STFXXRRQKFUYEU-UHFFFAOYSA-N 16-methylheptadecyl prop-2-enoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C=C STFXXRRQKFUYEU-UHFFFAOYSA-N 0.000 description 7
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 7
- 239000005058 Isophorone diisocyanate Substances 0.000 description 7
- 125000005442 diisocyanate group Chemical group 0.000 description 7
- 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 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- 229940117969 neopentyl glycol Drugs 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 229920000193 polymethacrylate Polymers 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 5
- 229920001083 polybutene Polymers 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 150000003505 terpenes Chemical class 0.000 description 5
- 235000007586 terpenes Nutrition 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 229920002799 BoPET Polymers 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229940106691 bisphenol a Drugs 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 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 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 150000007519 polyprotic acids Polymers 0.000 description 4
- MSFGZHUJTJBYFA-UHFFFAOYSA-M sodium dichloroisocyanurate Chemical compound [Na+].ClN1C(=O)[N-]C(=O)N(Cl)C1=O MSFGZHUJTJBYFA-UHFFFAOYSA-M 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 239000013638 trimer Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000007809 chemical reaction catalyst Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 150000002440 hydroxy compounds Chemical class 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000004843 novolac epoxy resin Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920001195 polyisoprene Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000004904 shortening Methods 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 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
- 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 2
- QFSYADJLNBHAKO-UHFFFAOYSA-N 2,5-dihydroxy-1,4-benzoquinone Chemical compound OC1=CC(=O)C(O)=CC1=O QFSYADJLNBHAKO-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
- DOFIAZGYBIBEGI-UHFFFAOYSA-N 3-sulfanylphenol Chemical compound OC1=CC=CC(S)=C1 DOFIAZGYBIBEGI-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- AJVQRCCUFIAJCU-UHFFFAOYSA-N N=C=O.N=C=O.CC1CCCC(C)(C)C1 Chemical compound N=C=O.N=C=O.CC1CCCC(C)(C)C1 AJVQRCCUFIAJCU-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6204—Polymers of olefins
- C08G18/6208—Hydrogenated polymers of conjugated dienes
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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
Description
本発明は、水添ポリブタジエンポリオールを主骨格とするウレタン(メタ)アクリレート及び(メタ)アクリル酸エステル化合物を含む樹脂組成物に関する。さらに本発明の樹脂組成物の硬化皮膜は柔軟性、透明性、耐湿性、基材への密着性に優れ、硬化収縮も少ないため、特に、ディスプレイ装置の光学フィルムなどの貼り合わせ用途として有用である。 The present invention relates to a resin composition containing a urethane (meth) acrylate having a hydrogenated polybutadiene polyol as a main skeleton and a (meth) acrylic acid ester compound. Furthermore, since the cured film of the resin composition of the present invention is excellent in flexibility, transparency, moisture resistance, adhesion to a substrate, and has little curing shrinkage, it is particularly useful for bonding applications such as optical films for display devices. is there.
従来より、ポリオール化合物とポリイソシアネート化合物及び水酸基含有(メタ)アクリレート化合物の反応物であるウレタン(メタ)アクリレートはコーティング剤、接着剤、フォトレジスト等の用途として多く使用されている。例えば特許文献1のような特に光学用途などの黄変による劣化が問題になる分野では、透明性の高いポリオール化合物と脂肪族あるいは脂環式のポリイソシアネートをベースにウレタン(メタ)アクリレート化合物を設計する。 Conventionally, urethane (meth) acrylate, which is a reaction product of a polyol compound, a polyisocyanate compound, and a hydroxyl group-containing (meth) acrylate compound, has been widely used for applications such as coating agents, adhesives, and photoresists. For example, in the field where degradation due to yellowing such as Patent Document 1 is particularly problematic, a urethane (meth) acrylate compound is designed based on a highly transparent polyol compound and an aliphatic or alicyclic polyisocyanate. To do.
更に過酷な条件に曝された場合の黄変性あるいは耐候性への改善として水添ポリブタジエンをポリオール化合物として選定して特長を出す場合がある。特許文献2では水添ポリブタジエンポリオールを使用してウレタン(メタ)アクリレートを製造している。硬化物としては耐候性に優れているが、水添ポリブタジエン骨格として疎水性が非常に高く、組成物として配合できるモノマーや添加剤との相溶性に限りがあると考えられる。また、使用している水添ポリブタジエンポリオールは比較的ヨウ素価が高く、現在要求されている耐候性や耐光性に満足する特性を与えない可能性が示唆される。さらには、ウレタン(メタ)アクリレートの樹脂として無希釈で製造するため、実際の工業化にあたっては粘度が高く作業性の面において課題が出る可能性がある。 In some cases, hydrogenated polybutadiene is selected as a polyol compound to improve yellowing or weather resistance when exposed to harsh conditions. In Patent Document 2, urethane (meth) acrylate is produced using hydrogenated polybutadiene polyol. Although it is excellent in weather resistance as a cured product, it is considered that the hydrogenated polybutadiene skeleton has very high hydrophobicity and is limited in compatibility with monomers and additives that can be blended as a composition. In addition, the hydrogenated polybutadiene polyol used has a relatively high iodine value, suggesting the possibility that it does not give properties that satisfy the currently required weather resistance and light resistance. Furthermore, since it is manufactured as a urethane (meth) acrylate resin without dilution, the actual industrialization has a high viscosity and may cause problems in terms of workability.
近年ではウレタン(メタ)アクリレートをLCD(液晶ディスプレイ)用途での検討や実績化が盛んになってきている。例えば特許文献3ではポリブタジエン系(メタ)アクリレートオリゴマー及びウレタン(メタ)アクリレートオリゴマーを使用した光学表示体又はタッチセンサーの貼り合わせに使用される光硬化型接着剤組成物として活用されている。ウレタン(メタ)アクリレートとしては、柔軟性に優れより耐候性や耐光性が高いものが今後も要求されることが推測される。又、特許文献4では芳香族環を有しないポリオール化合物を使用したウレタン(メタ)アクリレートのLCD光学部材への適用が記載されている。 In recent years, studies and achievements of urethane (meth) acrylates for LCD (liquid crystal display) applications have become active. For example, in patent document 3, it is utilized as a photocurable adhesive composition used for bonding of an optical display or a touch sensor using a polybutadiene-based (meth) acrylate oligomer and a urethane (meth) acrylate oligomer. As urethane (meth) acrylate, it is estimated that the thing excellent in a softness | flexibility and the weather resistance and light resistance will be requested | required from now on. Patent Document 4 describes the application of urethane (meth) acrylate using a polyol compound having no aromatic ring to an LCD optical member.
これらディスプレイ用途などに代表される光学部材用途としては、更に高い耐候性や耐光性と硬化膜物性の向上、他樹脂やモノマー類及び添加剤との相溶性改善がウレタン(メタ)アクリレートには要求され、更に工業化にあたっては実生産ラインを想定し、作業性の優れたウレタン(メタ)アクリレート材料及び組成物の詳細設計が今後も要求される。 For optical member applications represented by these display applications, urethane (meth) acrylates require higher weather resistance, light resistance, improved cured film properties, and improved compatibility with other resins, monomers, and additives. Further, in the industrialization, detailed design of urethane (meth) acrylate materials and compositions having excellent workability will be required in the future, assuming an actual production line.
本発明は、上記要求を改善し、耐候性や耐光性に優れると共に、柔軟性に優れた硬化膜を与え、硬化の際の収縮率が低い樹脂組成物を提供することを目的とする。 An object of the present invention is to provide a resin composition that improves the above-described requirements, provides a cured film having excellent weather resistance and light resistance, and excellent flexibility, and has a low shrinkage upon curing.
本発明者らは前期課題を解決するため、鋭意検討を行った結果、特定の化合物及び組成を有する樹脂組成物が前記課題を解決することを見いだし、本発明に到達した。 As a result of intensive studies in order to solve the previous problems, the present inventors have found that a resin composition having a specific compound and composition can solve the problems, and have reached the present invention.
即ち、本発明は、
(1)下記に示される化合物(A)と化合物(B)、化合物(C)、化合物(D)を反応させて得られるポリウレタン樹脂(E)および化合物(A)の(メタ)アクリル酸エステル化合物(F)を含有することを特徴とする樹脂組成物(G)、
化合物(A):水添ポリブタジエンポリオール化合物
化合物(B):ポリイソシアネート化合物
化合物(C):少なくとも1つ以上の水酸基を有する(メタ)アクリレート化合物
化合物(D):化合物(A)以外のジオール化合物
(2)水添ポリブタジエンポリオール化合物(A)のヨウ素価が20以下である(1)に記載の樹脂組成物(G)、
(3)ポリイソシアネート化合物(B)が脂肪族系ジイソシアネート化合物である(1)又は(2)に記載の樹脂組成物(G)、
(4)少なくとも1つ以上の水酸基を有する(メタ)アクリレート化合物(C)が2−ヒドロキシエチル(メタ)アクリレートである(1)乃至(3)のいずれか一項記載の樹脂組成物(G)、
(5)化合物(A)以外のジオール化合物(D)がポリエーテルポリオールである(1)乃至(4)のいずれか一項記載の樹脂組成物(G)、
(6)(1)乃至(5)のいずれか一項記載の樹脂組成物(G)と(G)以外の重合性化合物(H)を含有することを特徴とする重合性樹脂組成物、
(7)重合性化合物(H)がアルキル(メタ)アクリレート又はアルキレン(メタ)アクリレートである(6)記載の重合性樹脂組成物、
(8)(6)又は(7)に記載の重合性組成物と光重合開始剤(I)を含有する(6)又は(7)に記載の感光性樹脂組成物、
(9)(1)乃至(8)のいずれか一項記載の樹脂組成物の硬化物、
に関する。
That is, the present invention
(1) Polyurethane resin (E) obtained by reacting compound (A) with compound (B), compound (C) and compound (D) shown below and (meth) acrylic acid ester compound of compound (A) A resin composition (G) containing (F),
Compound (A): Hydrogenated polybutadiene polyol compound Compound (B): Polyisocyanate compound Compound (C): (Meth) acrylate compound having at least one hydroxyl group Compound (D): Diol compound other than compound (A) ( 2) The resin composition (G) according to (1), wherein the iodine value of the hydrogenated polybutadiene polyol compound (A) is 20 or less,
(3) The resin composition (G) according to (1) or (2), wherein the polyisocyanate compound (B) is an aliphatic diisocyanate compound,
(4) The resin composition (G) according to any one of (1) to (3), wherein the (meth) acrylate compound (C) having at least one hydroxyl group is 2-hydroxyethyl (meth) acrylate. ,
(5) The resin composition (G) according to any one of (1) to (4), wherein the diol compound (D) other than the compound (A) is a polyether polyol.
(6) A polymerizable resin composition comprising the resin composition (G) according to any one of (1) to (5) and a polymerizable compound (H) other than (G),
(7) The polymerizable resin composition according to (6), wherein the polymerizable compound (H) is an alkyl (meth) acrylate or an alkylene (meth) acrylate,
(8) The photosensitive resin composition according to (6) or (7), which contains the polymerizable composition according to (6) or (7) and a photopolymerization initiator (I),
(9) A cured product of the resin composition according to any one of (1) to (8),
About.
本発明のポリウレタン化合物および(メタ)アクリル酸化合物を含有する感光性樹脂組成物の硬化膜は、柔軟性に優れ、耐候性、耐光性が高く、透明性の維持が必要である光学用途以外にも、インキ、プラスチック塗料、紙印刷、金属コーティング、家具の塗装など種々のコーティング分野、ライニング、接着剤、更にはエレクトロニクス分野における絶縁ワニス、絶縁シート、積層板、プリント基板、レジストインキ、半導体封止剤などの多くの分野に応用が可能である。 The cured film of the photosensitive resin composition containing the polyurethane compound and (meth) acrylic acid compound of the present invention has excellent flexibility, high weather resistance, high light resistance, and optical use that needs to maintain transparency. In addition, various coating fields such as ink, plastic paint, paper printing, metal coating, furniture painting, lining, adhesives, and insulating varnish, insulating sheet, laminate, printed circuit board, resist ink, semiconductor encapsulation in the electronics field It can be applied to many fields such as drugs.
本発明で使用するポリウレタン樹脂(E)は水添ポリブタジエンポリオール(A)及び化合物(A)以外のジオール化合物(D)とポリイソシアネート化合物(B)とまず反応(以下第一の反応と呼ぶ)させ、続いて残存するイソシアネート基に対し少なくとも1つ以上の水酸基を有する(メタ)アクリレート化合物(C)を反応(以下第二の反応と呼ぶ)させることを特徴とする。 The polyurethane resin (E) used in the present invention is first reacted with the diol compound (D) other than the hydrogenated polybutadiene polyol (A) and the compound (A) and the polyisocyanate compound (B) (hereinafter referred to as the first reaction). Then, the (meth) acrylate compound (C) having at least one hydroxyl group is reacted with the remaining isocyanate group (hereinafter referred to as a second reaction).
本発明の第一の反応で使用する水添ポリブタジエンポリオール(A)としては、一般的なポリブタジエンポリオールの水素添加還元生成物であれば使用できるが、特に光学用途に関しては残留二重結合が少ないものが好ましく、ヨウ素価としては20以下がより好ましく、15以下が特に好ましい。また、(A)の分子量に関しては一般的に入手できる分子量分布のものは全て使用できるが、特に柔軟性と硬化性のバランスをとった場合には数平均分子量が500〜5000のものが好ましく、500〜3000のものが特に好ましい。 As the hydrogenated polybutadiene polyol (A) used in the first reaction of the present invention, any hydrogenated reduction product of a general polybutadiene polyol can be used. The iodine value is more preferably 20 or less, and particularly preferably 15 or less. As for the molecular weight of (A), all generally available molecular weight distributions can be used, but those having a number average molecular weight of 500 to 5,000 are particularly preferred when balancing the flexibility and curability, The thing of 500-3000 is especially preferable.
本発明の第一の反応で任意成分として使用する化合物(A)以外のジオール化合物(D)の具体例としては、例えば、ポリエチレングリコール、ポリブチレングリコール、ポリテトラメチレングリコール、ポリプロピレングリコール、ポリエチレングリコール等のポリエーテルポリオール類、ポリエチレングリコールアジペート、ポリ1,4−ブタンジオールアジペート、ポリカプロラクトン等のポリエステルポリオール類、エチレングリコール、プロピレングリコール、ブタンジオール、ペンタンジオール、ヘキサンジオール及びネオペンチルグリコール等のグリコール、シクロヘキサンジメチロール、水添ビスフェノールA、水添ビスフェノールF、スピロ骨格含有アルコール、トリシクロデカンジメチロール及びペンタシクロペンタデカンジメチロール等の脂環式アルコール及びこれらのアルキレンオキサイド付加物、水添ポリブタジエンのジオール等の分岐状又は直鎖状長鎖アルキルジオール、ビスフェノールA、ビスフェノールF等のビスフェノール類、並びにビスフェノールのアルキレンオキサイド付加物、トリメチロールプロパン、ジトリメチロールプロパン、ペンタエリスリトール及びジペンタエリスリトール等のポリオール、並びにこれらポリオールのアルキレンオキサイド付加物、更にはこれらのポリオールとアジピン酸等の多塩基酸の反応によって得られるポリエステルポリオール等を挙げることができる。特に限定はされないが、本発明の感光性樹脂組成物の硬化物において柔軟性と相溶性の向上させるためにはポリエーテルポリオール類の使用が特に好ましい。
このような化合物(A)以外のジオール化合物(D)の分子量に関しては一般的に入手できる分子量分布のものは全て使用できるが、特に柔軟性と硬化性のバランスをとった場合には数平均分子量が500〜6000のものが好ましく、500〜4000のものが特に好ましい。
そして、特に好適に使用される化合物(A)以外のジオール化合物(D)は分子量500〜4000のポリエーテルポリオール類である。
Specific examples of the diol compound (D) other than the compound (A) used as an optional component in the first reaction of the present invention include, for example, polyethylene glycol, polybutylene glycol, polytetramethylene glycol, polypropylene glycol, polyethylene glycol, etc. Polyether polyols, polyethylene glycol adipate, poly 1,4-butanediol adipate, polyester polyols such as polycaprolactone, glycols such as ethylene glycol, propylene glycol, butanediol, pentanediol, hexanediol and neopentylglycol, cyclohexane Dimethylol, hydrogenated bisphenol A, hydrogenated bisphenol F, spiro skeleton-containing alcohol, tricyclodecane dimethylol and pentacyclopentade Cycloaliphatic alcohols such as dimethylol and alkylene oxide adducts thereof, branched or linear long-chain alkyl diols such as diols of hydrogenated polybutadiene, bisphenols such as bisphenol A and bisphenol F, and alkylene oxide additions of bisphenols , Polyols such as trimethylolpropane, ditrimethylolpropane, pentaerythritol and dipentaerythritol, alkylene oxide adducts of these polyols, polyester polyols obtained by reaction of these polyols with polybasic acids such as adipic acid, etc. Can be mentioned. Although there is no particular limitation, it is particularly preferable to use polyether polyols in order to improve flexibility and compatibility in the cured product of the photosensitive resin composition of the present invention.
As for the molecular weight of the diol compound (D) other than the compound (A), all generally available molecular weight distributions can be used, but in particular, when the balance between flexibility and curability is balanced, the number average molecular weight Is preferably 500 to 6000, particularly preferably 500 to 4000.
The diol compound (D) other than the compound (A) that is particularly preferably used is a polyether polyol having a molecular weight of 500 to 4000.
ここで、本願発明においては、水添ポリブタジエンポリオール(A)及び(A)以外のジオール化合物(D)を反応に用いるところ、水添ポリブタジエン(A)及び(A)以外のジオール化合物(D)の使用比率は特に限定されないが、(A)成分:(D)成分はモル比で9.999:0.001〜2:8が好ましく、9.999:0.001〜5:5がより好ましく、9.999:0.001〜7:3が特に好ましい。 Here, in this invention, when diol compound (D) other than hydrogenated polybutadiene polyol (A) and (A) is used for reaction, diol compound (D) other than hydrogenated polybutadiene (A) and (A) is used. The use ratio is not particularly limited, but (A) component: (D) component is preferably 9.999: 0.001-2: 8 in terms of molar ratio, more preferably 9.999: 0.001-5: 5, Especially preferred is 9.999: 0.001-7: 3.
本発明の第一の反応で使用するポリイソシアネート化合物(B)は、1分子中にイソシアネート基を2個以上含んでなる化合物であり、例えば、脂肪族系ジイソシアネ−ト化合物、芳香族系ジイソシアネ−ト化合物、これらの3量体等が挙げられる。ここで言う脂肪族系ジイソシアネート化合物とは、イソシアネート基が鎖状炭素原子に結合したジイソシアネート化合物と、イソシアネート基が環状飽和炭化水素の炭素原子に結合したジイソシアネート化合物とを意味し、芳香族系ジイソシアネート化合物とは、イソシアネート基が芳香環の炭素原子に結合したイソシアネート化合物を意味する。透明性を付与する観点からは、脂肪族系ジイソシアネート化合物が好ましい。 The polyisocyanate compound (B) used in the first reaction of the present invention is a compound containing two or more isocyanate groups in one molecule, and examples thereof include aliphatic diisocyanate compounds and aromatic diisocyanates. Compounds, trimers thereof, and the like. The aliphatic diisocyanate compound as used herein means a diisocyanate compound in which an isocyanate group is bonded to a chain carbon atom, and a diisocyanate compound in which an isocyanate group is bonded to a carbon atom of a cyclic saturated hydrocarbon, and an aromatic diisocyanate compound. Means an isocyanate compound in which an isocyanate group is bonded to a carbon atom of an aromatic ring. From the viewpoint of imparting transparency, an aliphatic diisocyanate compound is preferred.
脂肪族系ジイソシアネート化合物としては、例えば、1,6−ヘキサメチレンジイソシアネート、イソホロンジイソシアネート、水添トリレンジイソシアネート、水添キシリレンジイソシアネート、水添ジフェニルメタンジイソシアネート、1,3−ジイソシアネートシクロヘキサン、1,4−ジイソシアネートシクロヘキサン、ジシクロヘキシルメタン−4,4′−ジイソシアネート、m−テトラメチルキシレンジイソシアネート、p−テトラメチルキシレンジイソシアネート、1,4−テトラメチレンジイソシアネート、1,12−ドデカメチレンジイソシアネート、2,2,4−トリメチルシクロヘキサンジイソシアネート、2,4,4−トリメチルシクロヘキサンジイソシアネート、2,2,4−トリメチルヘキサメチレンジイソシアネート、2,4,4−トリメチルヘキサメチレンジイソシアネート、リジンジイソシアネート、ノルボルナンジイソシアネート等が挙げられる。中でも、イソホロンジイソシアネートが好ましい。
Examples of the aliphatic diisocyanate compound include 1,6-hexamethylene diisocyanate, isophorone diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, 1,3-diisocyanate cyclohexane, and 1,4-diisocyanate. Cyclohexane, dicyclohexylmethane-4,4'-diisocyanate, m-tetramethylxylene diisocyanate, p-tetramethylxylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,12-dodecamethylene diisocyanate, 2,2,4-trimethylcyclohexane Diisocyanate, 2,4,4-trimethylcyclohexane diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate Sulfonate, 2,4,4-trimethylhexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate and the like. Of these, isophorone diisocyanate is preferred.
芳香族系ジイソシアネート化合物としては、例えば、トリレンジイソシアネート、キシリレンジイソシアネート、ジフェニルメタンジイソシアネート、1,5−ナフタレンジイソシアネート、トリジンジイソシアネート、1,6−フェニレンジイソシアネート、1,4−フェニレンジイソシアネート、1,6−フェニレンジイソシアネート等ジイソシアネートモノマー類等が挙げられる。 Examples of the aromatic diisocyanate compound include tolylene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, 1,5-naphthalene diisocyanate, tolidine diisocyanate, 1,6-phenylene diisocyanate, 1,4-phenylene diisocyanate, 1,6-phenylene. And diisocyanate monomers such as diisocyanate.
このうち、脂肪族系ジイソシアネート化合物、および、該脂肪族系ジイソシアネート化合物の3量体が、塗膜の耐候性を良好とするため好ましい。脂肪族系ジイソシアネート化合物の3量体としては、例えば、上記脂肪族系イソシアネ−ト系のイソシアヌレート型ポリイソシアネート等が挙げられ、具体的には、ヘキサメチレンジイソシアネートやイソホロンジイソシアネート等が挙げられる。これらは各々単独あるいは混合物で用いても差し支えない。 Among these, an aliphatic diisocyanate compound and a trimer of the aliphatic diisocyanate compound are preferable because the weather resistance of the coating film is improved. Examples of the trimer of the aliphatic diisocyanate compound include the above-mentioned aliphatic isocyanate-based isocyanurate-type polyisocyanates, and specific examples include hexamethylene diisocyanate and isophorone diisocyanate. These may be used alone or in a mixture.
本発明において、第一の反応は、反応後にイソシアネート基が残存するような当量関係(B/(A+D)>1:[NCO]/[OH]モル比)で仕込む。仕込み比を高くすると未反応のポリイソシアネート化合物(B)が多く存在し、感光性樹脂組成物の柔軟性に影響を及ぼす場合がある。また仕込み比を小さくすると、分子量が高くなり、感光性樹脂組成物の硬化性に影響を及ぼす場合がある。具体的に好ましくは、ポリイソシアネート化合物(B)のNCO基1.0モルに対しアルコール化合物(A+D)のOH基を0.1〜0.9モルが好ましく、0.4〜0.7モルがより好ましい。 In the present invention, the first reaction is carried out in an equivalent relationship (B / (A + D)> 1: [NCO] / [OH] molar ratio) such that isocyanate groups remain after the reaction. When the charging ratio is increased, a large amount of unreacted polyisocyanate compound (B) is present, which may affect the flexibility of the photosensitive resin composition. On the other hand, when the preparation ratio is reduced, the molecular weight is increased and the curability of the photosensitive resin composition may be affected. Specifically, the OH group of the alcohol compound (A + D) is preferably 0.1 to 0.9 mol, and 0.4 to 0.7 mol is preferably 1.0 mol of the NCO group of the polyisocyanate compound (B). More preferred.
本発明において、第一の反応は、無溶剤で行うことができるが、生成物の粘度が高く作業性向上のためアルコール性水酸基を有さない溶剤中あるいは後述する重合性化合物(F)中で行なうことが好ましい。溶剤の具体例としては、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン類、ベンゼン、トルエン、キシレン、テトラメチルベンゼン等の芳香族炭化水素類、エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、ジプロピレングリコールジメチルエーテル、ジプロピレングリコールジエチルエーテル、トリエチレングリコールジメチルエーテル、トリエチレングリコールジエチルエーテル等のグリコールエーテル類、酢酸エチル、酢酸ブチル、メチルセロソルブアセテート、エチルセロソルブアセテート、ブチルセロソルブアセテート、カルビトールアセテート、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、ジプロピレングリコールモノメチルエーテルアセテート、グルタル酸ジアルキル、コハク酸ジアルキル、アジピン酸ジアルキル等のエステル類、γ−ブチロラクトン等の環状エステル類、石油エーテル、石油ナフサ、水添石油ナフサ、ソルベントナフサ等の石油系溶剤等の単独又は混合有機溶媒中で行うことができる。 In the present invention, the first reaction can be carried out without a solvent, but in a solvent having a high viscosity of the product and having no alcoholic hydroxyl group for improving workability or in a polymerizable compound (F) described later. It is preferable to do so. Specific examples of the solvent include ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, aromatic hydrocarbons such as benzene, toluene, xylene, and tetramethylbenzene, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and dipropylene glycol. Glycol ethers such as dimethyl ether, dipropylene glycol diethyl ether, triethylene glycol dimethyl ether, triethylene glycol diethyl ether, ethyl acetate, butyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, butyl cellosolve acetate, carbitol acetate, propylene glycol monomethyl ether acetate , Propylene glycol monoethyl ether acetate, Propylene glycol monomethyl ether acetate, esters such as dialkyl glutarate, dialkyl succinate and dialkyl adipate, cyclic esters such as γ-butyrolactone, petroleum solvents such as petroleum ether, petroleum naphtha, hydrogenated petroleum naphtha and solvent naphtha Can be carried out alone or in a mixed organic solvent.
反応温度は通常30〜150℃、好ましくは50〜100℃の範囲である。反応の終点はイシアネート量の減少で確認する。また、これらの反応時間の短縮を目的として触媒を添加してもよい。この触媒としては、塩基性触媒及び酸性触媒のいずれかが用いられる。塩基性触媒の例としては、ピリジン、ピロール、トリエチルアミン、ジエチルアミン、ジブチルアミン、アンモニアなどのアミン類、トリブチルホスフィン、トリフェニルホスフィン等のホスフィン類を挙げることができる。また酸性触媒の例としては、ナフテン酸銅、ナフテン酸コバルト、ナフテン酸亜鉛、トリブトキシアルミニウム、チタニウムテトライソプロポキシド、ジルコニウムテトラブトキシド、塩化アルミニウム、オクチル酸スズ、オクチルスズトリラウレート、ジブチルスズジラウレート、オクチルスズジアセテート等のルイス酸触媒を挙げることができる。これら触媒の添加量は、ジオール化合物(A+D)とポリイソシアネート化合物(B)の総重量部100重量部に対して、通常0.1〜1重量部である。 The reaction temperature is usually 30 to 150 ° C, preferably 50 to 100 ° C. The end point of the reaction is confirmed by a decrease in the amount of isocyanate. A catalyst may be added for the purpose of shortening the reaction time. As this catalyst, either a basic catalyst or an acidic catalyst is used. Examples of the basic catalyst include amines such as pyridine, pyrrole, triethylamine, diethylamine, dibutylamine and ammonia, and phosphines such as tributylphosphine and triphenylphosphine. Examples of acidic catalysts include copper naphthenate, cobalt naphthenate, zinc naphthenate, tributoxyaluminum, titanium tetraisopropoxide, zirconium tetrabutoxide, aluminum chloride, tin octylate, octyltin trilaurate, dibutyltin dilaurate, Mention may be made of Lewis acid catalysts such as octyltin diacetate. The addition amount of these catalysts is 0.1-1 weight part normally with respect to 100 weight part of total weights of a diol compound (A + D) and a polyisocyanate compound (B).
本発明のポリウレタン樹脂(E)は第一の反応後、続いて残存するイソシアネート基に対し少なくとも1つ以上の水酸基を有する(メタ)アクリレート化合物(C)を反応(第二の反応)させて得ることができる。 The polyurethane resin (E) of the present invention is obtained by reacting (second reaction) a (meth) acrylate compound (C) having at least one hydroxyl group with respect to the remaining isocyanate group after the first reaction. be able to.
本発明の第二の反応で使用する少なくとも1つ以上の水酸基を有する(メタ)アクリレート化合物(C)とは、1分子中にヒドロキシル基と(メタ)アクリレートを少なくとも各々1個づつ有する化合物であり、具体的には、2−ヒドロキシエチル(メタ)アクリレート、プロピレングリコールモノ(メタ)アクリレート、ブタンジオールモノ(メタ)アクリレート、ペンタンジオールモノ(メタ)アクリレート、ヘキサンジオールモノ(メタ)アクリレート、ジエチレングリコールモノ(メタ)アクリレート、ジプロピレングリコールモノ(メタ)アクリレート、トリエチレングリコールモノ(メタ)アクリレート、トリプロピレングリコールモノ(メタ)アクリレート、テトラエチレングリコールモノ(メタ)アクリレート、ポリエチレングリコールモノ(メタ)アクリレート、ポリプロピレングリコールモノ(メタ)アクリレート、ネオペンチルグリコールモノ(メタ)アクリレート、エトキシ化ネオペンチルグリコールモノ(メタ)アクリレート、ヒドロキシピバリン酸ネオペンチルグリコールモノ(メタ)アクリレートなどの2価アルコールのモノ(メタ)アクリレート; The (meth) acrylate compound (C) having at least one hydroxyl group used in the second reaction of the present invention is a compound having at least one hydroxyl group and one (meth) acrylate in each molecule. Specifically, 2-hydroxyethyl (meth) acrylate, propylene glycol mono (meth) acrylate, butanediol mono (meth) acrylate, pentanediol mono (meth) acrylate, hexanediol mono (meth) acrylate, diethylene glycol mono ( (Meth) acrylate, dipropylene glycol mono (meth) acrylate, triethylene glycol mono (meth) acrylate, tripropylene glycol mono (meth) acrylate, tetraethylene glycol mono (meth) acrylate, polyethylene Divalent compounds such as glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, neopentyl glycol mono (meth) acrylate, ethoxylated neopentyl glycol mono (meth) acrylate, and hydroxypivalate neopentyl glycol mono (meth) acrylate Mono (meth) acrylate of alcohol;
トリメチロールプロパンモノ(メタ)アクリレート、エトキシ化トリメチロールプロパンモノ(メタ)アクリレート、プロポキシ化トリメチロールプロパンモノ(メタ)アクリレート、トリス(2−ヒドロキシエチル)イソシアヌレートモノ(メタ)アクリレート、グリセリンモノ(メタ)アクリレート、トリメチロールプロパンジ(メタ)アクリレート、エトキシ化トリメチロールプロパンジ(メタ)アクリレート、プロポキシ化トリメチロールプロパンジ(メタ)アクリレート、トリス(2−ヒドロキシエチル)イソシアヌレートジ(メタ)アクリレート、グリセリンジ(メタ)アクリレート等の3価のアルコールのモノアクリレート及びジ(メタ)アクリレートや、これらアルコールの水酸基の一部をアルキル基やε−カプロラクトンで変性したモノ及びジ(メタ)アクリレート; Trimethylolpropane mono (meth) acrylate, ethoxylated trimethylolpropane mono (meth) acrylate, propoxylated trimethylolpropane mono (meth) acrylate, tris (2-hydroxyethyl) isocyanurate mono (meth) acrylate, glycerin mono (meta) ) Acrylate, trimethylolpropane di (meth) acrylate, ethoxylated trimethylolpropane di (meth) acrylate, propoxylated trimethylolpropane di (meth) acrylate, tris (2-hydroxyethyl) isocyanurate di (meth) acrylate, glycerin Mono- and di (meth) acrylates of trivalent alcohols such as di (meth) acrylate, and some of the hydroxyl groups of these alcohols are alkyl groups or ε-caprolactone. Modified mono- and di (meth) acrylate;
ペンタエリスリトールモノ(メタ)アクリレート、ジペンタエリスリトールモノ(メタ)アクリレート、ジトリメチロールプロパンモノ(メタ)アクリレート、ペンタエリスリトールジ(メタ)アクリレート、ジペンタエリスリトールジ(メタ)アクリレート、ジトリメチロールプロパンジ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ジペンタエリスリトールトリ(メタ)アクリレート、ジトリメチロールプロパントリ(メタ)アクリレート、ジペンタエリスリトールテトラ(メタ)アクリレート、ジトリメチロールプロパンテトラ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、ジトリメチロールプロパンヘキサ(メタ)アクリレート等の、4価以上のアルコールの多官能(メタ)アクリレートでヒドロキシル基を有するものや、これらアルコールの水酸基の一部をアルキル基やε−カプロラクトンで変性したヒドロキシル基を有する多官能(メタ)アクリレート、等が挙げられる。 Pentaerythritol mono (meth) acrylate, dipentaerythritol mono (meth) acrylate, ditrimethylolpropane mono (meth) acrylate, pentaerythritol di (meth) acrylate, dipentaerythritol di (meth) acrylate, ditrimethylolpropane di (meth) Acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol tri (meth) acrylate, ditrimethylolpropane tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol hexa Polyfunctionals (meth) of tetrahydric or higher alcohols such as (meth) acrylate and ditrimethylolpropane hexa (meth) acrylate ) And those having a hydroxyl group in acrylates, polyfunctional (meth) acrylate having a hydroxyl group partially modified with an alkyl group and ε- caprolactone hydroxyl groups of these alcohols, and the like.
上記した少なくとも1つの水酸基を有する(メタ)アクリレート化合物(C)のうち、水酸基は一つであることが好ましく、硬化性と柔軟性に優れる点から、2−ヒドロキシエチル(メタ)アクリレートが特に好ましい。作業性容易な点から、本発明の中で後述する重合性化合物(F)を反応時に添加してもよい。 Of the above (meth) acrylate compound (C) having at least one hydroxyl group, one hydroxyl group is preferred, and 2-hydroxyethyl (meth) acrylate is particularly preferred from the viewpoint of excellent curability and flexibility. . From the viewpoint of easy workability, a polymerizable compound (F) described later in the present invention may be added during the reaction.
本発明の第二の反応は、第一の反応後に得られた中間体のイソシアネート基が無くなるような当量関係で仕込む。具体的に好ましくは、第一の反応後に得られた中間体のNCO基1.0molに対し少なくとも1つ以上の水酸基を有する(メタ)アクリレート化合物(C)のOH基を1.0〜3.0モル、更に好ましくは1.0〜2.0モルとする。 The second reaction of the present invention is charged in an equivalent relationship such that the isocyanate group of the intermediate obtained after the first reaction is eliminated. Specifically, preferably, the OH group of the (meth) acrylate compound (C) having at least one hydroxyl group is 1.0 to 3.3 with respect to 1.0 mol of the NCO group of the intermediate obtained after the first reaction. 0 mol, more preferably 1.0 to 2.0 mol.
本発明の第二の反応も、無溶剤で行うことができるが、生成物の粘度が高く作業性向上のため上述した溶剤中及び/又は本発明の中で後述する重合性化合物(H)の存在下で行うことが好ましい。また、反応温度は通常30〜150℃、好ましくは50〜100℃の範囲である。反応の終点はイシアネート量の減少で確認する。これらの反応時間の短縮を目的として前述の触媒を添加してもよい。 The second reaction of the present invention can also be carried out in the absence of a solvent. However, the product has a high viscosity and the above-described solvent and / or polymerizable compound (H) described later in the present invention is used for improving workability. It is preferably carried out in the presence. Moreover, reaction temperature is 30-150 degreeC normally, Preferably it is the range of 50-100 degreeC. The end point of the reaction is confirmed by a decrease in the amount of isocyanate. The aforementioned catalyst may be added for the purpose of shortening the reaction time.
原料として用いる(メタ)アクリレート化合物には、既に4−メトキシフェノール等の重合禁止剤が添加されているのが普通であるが、反応時に改めて重合禁止剤を添加してもよい。そのような重合禁止剤の例としては、ハイドロキノン、4−メトキシフェノール、2,4−ジメチル−6−t−ブチルフェノール、2,6−ジ−t−ブチル−4−クレゾール、3−ヒドロキシチオフェノール、p−ベンゾキノン、2,5−ジヒドロキシ−p−ベンゾキノン、フェノチアジン等が挙げられる。その使用量は反応原料混合物に対し0.01〜1重量%である。 Usually, a polymerization inhibitor such as 4-methoxyphenol is already added to the (meth) acrylate compound used as a raw material, but a polymerization inhibitor may be added again during the reaction. Examples of such polymerization inhibitors include hydroquinone, 4-methoxyphenol, 2,4-dimethyl-6-t-butylphenol, 2,6-di-t-butyl-4-cresol, 3-hydroxythiophenol, Examples include p-benzoquinone, 2,5-dihydroxy-p-benzoquinone, and phenothiazine. The amount used is 0.01 to 1% by weight based on the reaction raw material mixture.
本発明で使用する(メタ)アクリル酸エステル化合物(F)は上述の水添ポリブタジエンポリオール化合物(A)と(メタ)アクリル酸を酸触媒の存在下で脱水縮合させる方法により製造できる。 The (meth) acrylic acid ester compound (F) used in the present invention can be produced by a method of dehydrating and condensing the hydrogenated polybutadiene polyol compound (A) and (meth) acrylic acid in the presence of an acid catalyst.
反応させる際に使用する(メタ)アクリル酸の使用量は水添ポリブタジエンポリオール化合物(A)の水酸基1.0molに対し、0.8〜3.0molが好ましく、1.0〜2.0が更に好ましい。 The amount of (meth) acrylic acid used in the reaction is preferably from 0.8 to 3.0 mol, more preferably from 1.0 to 2.0, based on 1.0 mol of the hydroxyl group of the hydrogenated polybutadiene polyol compound (A). preferable.
反応させる際に使用する酸触媒は、硫酸、メタンスルホン酸、p−トルエンスルホン酸等公知のものから任意に選択でき、その使用量は、(メタ)アクリル酸に対して0.1〜10モル%、好ましくは1〜5モル%である。 The acid catalyst used in the reaction can be arbitrarily selected from known ones such as sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid, and the amount used is 0.1 to 10 mol with respect to (meth) acrylic acid. %, Preferably 1 to 5 mol%.
反応により生成した水を留去するのには共沸溶媒を用いることができる。ここでいう共沸溶媒とは60〜130℃の沸点を有し、水と容易に分離できるものであり、特に、n−ヘキサン、n−ヘプタン等の脂肪族炭化水素、ベンゼン、トルエン等の芳香族炭化水素、シクロヘキサン等の脂環式炭化水素の使用が好ましい。その使用量は任意であるが、好ましくは反応混合物に対し10〜70重量%である。 An azeotropic solvent can be used to distill off the water produced by the reaction. The azeotropic solvent here has a boiling point of 60 to 130 ° C. and can be easily separated from water, and in particular, aliphatic hydrocarbons such as n-hexane and n-heptane, and aromatics such as benzene and toluene. The use of alicyclic hydrocarbons such as aromatic hydrocarbons and cyclohexane is preferred. The amount used is arbitrary, but is preferably 10 to 70% by weight based on the reaction mixture.
原料として用いる市販品の(メタ)アクリル酸等には、既にp−メトキシフェノール等の重合禁止剤が添加されているのが普通であるが、反応時に改めて重合禁止剤を添加してもよい。そのような重合禁止剤の例としては、ハイドロキノン、p−メトキシフェノール、2,4−ジメチル−6−t−ブチルフェノール、3−ヒドロキシチオフェノール、p−ベンゾキノン、2,5−ジヒドロキシ−p−ベンゾキノン、フェノチアジン等が挙げられる。その使用量は反応原料混合物に対し0.01〜1重量%である。 A commercially available (meth) acrylic acid or the like used as a raw material is usually already added with a polymerization inhibitor such as p-methoxyphenol, but a polymerization inhibitor may be added again during the reaction. Examples of such polymerization inhibitors include hydroquinone, p-methoxyphenol, 2,4-dimethyl-6-t-butylphenol, 3-hydroxythiophenol, p-benzoquinone, 2,5-dihydroxy-p-benzoquinone, Examples include phenothiazine. The amount used is 0.01 to 1% by weight based on the reaction raw material mixture.
反応温度は60〜130℃の範囲でよいが、反応時間の短縮と重合防止の点から、75〜120℃で行なうのが好ましい。反応は生成する水の量で進行を確認することができ、水の生成が止まったところを反応の終了と判定する。 反応終了後、一般的な後処理と同様に水洗処理等を実施して、反応に溶媒等を使用していれば減圧留去にて取り除くことで本発明の(メタ)アクリル酸エステル化合物(F)を得ることができる。 The reaction temperature may be in the range of 60 to 130 ° C, but is preferably 75 to 120 ° C from the viewpoint of shortening the reaction time and preventing polymerization. The progress of the reaction can be confirmed by the amount of water produced, and it is determined that the reaction has ended when the production of water has stopped. After completion of the reaction, washing with water is carried out in the same manner as general post-treatment, and if a solvent or the like is used in the reaction, the (meth) acrylic acid ester compound (F) of the present invention is removed by distillation under reduced pressure. ) Can be obtained.
本発明で使用する(メタ)アクリル酸エステル化合物(F)は市販のものも使用でき、例えば大阪有機化学工業(株)製SPBDA−S30等が挙げられる。 As the (meth) acrylic acid ester compound (F) used in the present invention, a commercially available product can be used, and examples thereof include SPBDA-S30 manufactured by Osaka Organic Chemical Industry Co., Ltd.
こうして、本発明においては、ポリウレタン樹脂(E)と化合物(A)の(メタ)アクリル酸エステル化合物(F)を含有することとなる。
ここで、本発明の感光性樹脂組成物においては、ポリウレタン化合物(E)と化合物(A)の(メタ)アクリル酸エステル化合物(F)の重量比は10:1〜1:1で含有させることが好ましく、5:1〜2:1であることがより好ましい。このようにポリウレタン化合物(E)の含有割合を化合物(A)の(メタ)アクリル酸エステル化合物(F)より多くすることで収縮率を抑えることができるためである。また、一定量以上ポリウレタン化合物(E)と化合物(A)の(メタ)アクリル酸エステル化合物(F)が存在することにより、硬化物の接着性及び剛性を高めることが可能となるためである。
さらに、本発明の感光性樹脂組成物においては、感光性樹脂組成物中化合物(A)の(メタ)アクリル酸エステル化合物(F)が1〜10重量%存在することが好ましく、3〜8重量%であることが特に好ましい。硬化物の接着性及び剛性を高めることが可能となるためである。
Thus, in the present invention, the polyurethane resin (E) and the (meth) acrylic acid ester compound (F) of the compound (A) are contained.
Here, in the photosensitive resin composition of the present invention, the weight ratio of the polyurethane compound (E) and the (meth) acrylic acid ester compound (F) of the compound (A) is 10: 1 to 1: 1. Is preferable, and 5: 1 to 2: 1 is more preferable. This is because the shrinkage rate can be suppressed by increasing the content ratio of the polyurethane compound (E) as compared with the (meth) acrylic acid ester compound (F) of the compound (A). Moreover, it is because it becomes possible to improve the adhesiveness and rigidity of hardened | cured material by the polyurethane compound (E) and the (meth) acrylic acid ester compound (F) of a compound (A) more than fixed amount existing.
Furthermore, in the photosensitive resin composition of the present invention, it is preferable that the (meth) acrylic acid ester compound (F) of the compound (A) is present in the photosensitive resin composition in an amount of 1 to 10% by weight, and 3 to 8% by weight. % Is particularly preferred. It is because it becomes possible to improve the adhesiveness and rigidity of hardened | cured material.
本発明の感光性樹脂組成物は、本発明のポリウレタン樹脂(E)及び(メタ)アクリル酸化合物(F)と(E)、(F)成分以外の重合性化合物(H)を任意成分として含有させることができる。使用しうる重合性化合物(H)の具体例としては、(メタ)アクリロイルオキシ基を有する化合物、マレイミド化合物、(メタ)アクリルアミド化合物、不飽和ポリエステル等を挙げることができる。 The photosensitive resin composition of the present invention contains the polyurethane resin (E) of the present invention and a (meth) acrylic acid compound (F) and a polymerizable compound (H) other than the components (E) and (F) as optional components. Can be made. Specific examples of the polymerizable compound (H) that can be used include a compound having a (meth) acryloyloxy group, a maleimide compound, a (meth) acrylamide compound, and an unsaturated polyester.
本発明の感光性樹脂組成物に併用可能な(メタ)アクリロイルオキシ基を有する化合物の具体例としては、(ポリ)エステル(メタ)アクリレート(H−1);ウレタン(メタ)アクリレート(H−2);エポキシ(メタ)アクリレート(H−3);(ポリ)エーテル(メタ)アクリレート(H−4);アルキル(メタ)アクリレート又はアルキレン(メタ)アクリレート(H−5);芳香環を有する(メタ)アクリレート(H−6);脂環構造を有する(メタ)アクリレート(H−7)等を挙げることができるが、これらに限定されるものではない。
尚、反応物については、公知の反応条件で得ることができる。
Specific examples of the compound having a (meth) acryloyloxy group that can be used in combination with the photosensitive resin composition of the present invention include (poly) ester (meth) acrylate (H-1); urethane (meth) acrylate (H-2). ); Epoxy (meth) acrylate (H-3); (poly) ether (meth) acrylate (H-4); alkyl (meth) acrylate or alkylene (meth) acrylate (H-5); having an aromatic ring (meta) ) Acrylate (H-6); (meth) acrylate (H-7) having an alicyclic structure, and the like can be mentioned, but the invention is not limited thereto.
In addition, about a reaction material, it can obtain on well-known reaction conditions.
本発明の感光性樹脂組成物に併用可能な(ポリ)エステル(メタ)アクリレート(H−1)とは、主鎖にエステル結合を1つ以上有する(メタ)アクリレートの総称として、ウレタン(メタ)アクリレート(H−2)とは、主鎖にウレタン結合を1つ以上有する(メタ)アクリレートの総称として、エポキシ(メタ)アクリレート(H−3)とは、1官能以上のエポキシ化合物と(メタ)アクリル酸を反応させて得られる(メタ)アクリレートの総称として、(ポリ)エーテル(メタ)アクリレート(H−4)とは、主鎖にエーテル結合を1つ以上有する(メタ)アクリレートの総称として、アルキル(メタ)アクリレート又はアルキレン(メタ)アクリレート(H−5)とは、主鎖が直鎖アルキル、分岐アルキル、直鎖又は末端にハロゲン原子及び/又は水酸基を有していてもよい(メタ)アクリレートの総称として、芳香環を有する(メタ)アクリレート(H−6)とは、主鎖又は側鎖に芳香環を有する(メタ)アクリレートの総称として、脂環構造を有する(メタ)アクリレート(H−7)とは、主鎖又は側鎖に、構成単位に酸素原子又は窒素原子を含んでいてもよい脂環構造を有する(メタ)アクリレートの総称として、それぞれ用いる。 The (poly) ester (meth) acrylate (H-1) that can be used in combination with the photosensitive resin composition of the present invention is a general term for (meth) acrylate having one or more ester bonds in the main chain, and urethane (meth). Acrylate (H-2) is a general term for (meth) acrylate having one or more urethane bonds in the main chain, and epoxy (meth) acrylate (H-3) is a monofunctional or higher functional epoxy compound and (meth). As a generic term for (meth) acrylate obtained by reacting acrylic acid, (poly) ether (meth) acrylate (H-4) is a generic term for (meth) acrylate having one or more ether bonds in the main chain, Alkyl (meth) acrylate or alkylene (meth) acrylate (H-5) means that the main chain is linear alkyl, branched alkyl, and linear or terminal halogen. As a general term for the (meth) acrylate which may have a child and / or a hydroxyl group, the (meth) acrylate (H-6) having an aromatic ring is a (meth) acrylate having an aromatic ring in the main chain or side chain. As a general term, (meth) acrylate (H-7) having an alicyclic structure has (meth) an alicyclic structure in which a structural unit may contain an oxygen atom or a nitrogen atom in the main chain or side chain. These are used as a general term for acrylates.
本発明の感光性樹脂組成物に併用可能な(ポリ)エステル(メタ)アクリレート(H−1)としては、例えば、カプロラクトン変性2−ヒドロキシエチル(メタ)アクリレート、エチレンオキサイド及び/又はプロピレンオキサイド変性フタル酸(メタ)アクリレート、エチレンオキサイド変性コハク酸(メタ)アクリレート、カプロラクトン変性テトラヒドロフルフリル(メタ)アクリレートの如き単官能(ポリ)エステル(メタ)アクリレート類;ヒドロキシピバリン酸エステルネオペンチルグリコールジ(メタ)アクリレート、カプロラクトン変性ヒドロキシピバリン酸エステルネオペンチルグリコールジ(メタ)アクリレート、エピクロルヒドリン変性フタル酸ジ(メタ)アクリレート;トリメチロールプロパン又はグリセリン1モルに1モル以上のε−カプロラクトン、γ−ブチロラクトン、δ−バレロラクトン等の環状ラクトン化合物を付加して得たトリオールのモノ、ジ又はトリ(メタ)アクリレート; Examples of the (poly) ester (meth) acrylate (H-1) that can be used in combination with the photosensitive resin composition of the present invention include caprolactone-modified 2-hydroxyethyl (meth) acrylate, ethylene oxide and / or propylene oxide-modified phthalate. Monofunctional (poly) ester (meth) acrylates such as acid (meth) acrylate, ethylene oxide modified succinic acid (meth) acrylate, caprolactone modified tetrahydrofurfuryl (meth) acrylate; hydroxypivalate ester neopentyl glycol di (meth) Acrylate, caprolactone-modified hydroxypivalate ester neopentyl glycol di (meth) acrylate, epichlorohydrin-modified phthalic acid di (meth) acrylate; trimethylolpropane or glycerol 1 1 mole or more ε- caprolactone, .gamma.-butyrolactone, .delta.-valerolactone of triol obtained by adding a cyclic lactone compound of mono-, di- or tri (meth) acrylate;
ペンタエリスリトール又はジトリメチロールプロパン1モルに1モル以上のε−カプロラクトン、γ−ブチロラクトン、δ−バレロラクトン等の環状ラクトン化合物を付加して得たテトラオールのモノ、ジ、トリ又はテトラ(メタ)アクリレート;ジペンタエリスリトール1モルに1モル以上のε−カプロラクトン、γ−ブチロラクトン、δ−バレロラクトン等の環状ラクトン化合物を付加して得たヘキサオールのモノ、又はポリ(メタ)アクリレート; Mono, di, tri or tetra (meth) acrylate of tetraol obtained by adding 1 mol or more of cyclic lactone compound such as ε-caprolactone, γ-butyrolactone, δ-valerolactone to 1 mol of pentaerythritol or ditrimethylolpropane Mono- or poly (meth) acrylate of hexaol obtained by adding 1 mol or more of cyclic lactone compound such as ε-caprolactone, γ-butyrolactone, δ-valerolactone to 1 mol of dipentaerythritol;
(ポリ)エチレングリコール、(ポリ)プロピレングリコール、(ポリ)テトラメチレングリコール、(ポリ)ブチレングリコール、3−メチル−1,5−ペンタンジオール、ヘキサンジオール等のジオール成分とマレイン酸、フマル酸、コハク酸、アジピン酸、フタル酸、イソフタル酸、ヘキサヒドロフタル酸、テトラヒドロフタル酸、ダイマー酸、セバチン酸、アゼライン酸、5−ナトリウムスルホイソフタル酸等の多塩基酸、及びこれらの無水物との反応物であるポリエステルポリオールの(メタ)アクリレート;前記ジオール成分と多塩基酸及びこれらの無水物とε−カプロラクトン、γ−ブチロラクトン、δ−バレロラクトン等からなる環状ラクトン変性ポリエステルジオールの(メタ)アクリレート等の多官能(ポリ)エステル(メタ)アクリレート類等を挙げることができるが、これらに限定されるものではない。 Diol components such as (poly) ethylene glycol, (poly) propylene glycol, (poly) tetramethylene glycol, (poly) butylene glycol, 3-methyl-1,5-pentanediol, hexanediol, maleic acid, fumaric acid, succinic acid Acids, adipic acid, phthalic acid, isophthalic acid, hexahydrophthalic acid, tetrahydrophthalic acid, dimer acid, sebacic acid, azelaic acid, polybasic acids such as 5-sodium sulfoisophthalic acid, and their reactants (Meth) acrylates of polyester polyols, such as (meth) acrylates of cyclic lactone-modified polyester diols composed of the diol component and polybasic acids and their anhydrides and ε-caprolactone, γ-butyrolactone, δ-valerolactone, etc. Multifunctional (poly) ester ( Can be mentioned data) acrylate, and the like, but is not limited thereto.
本発明の感光性樹脂組成物に併用可能なウレタン(メタ)アクリレート(H−2)は、少なくとも一つの(メタ)アクリロイルオキシ基を有するヒドロキシ化合物(H−2−イ)とイソシアネート化合物(H−2−ロ)との反応によって得られる(メタ)アクリレートの総称である。 The urethane (meth) acrylate (H-2) that can be used in combination with the photosensitive resin composition of the present invention comprises at least one (meth) acryloyloxy group-containing hydroxy compound (H-2-I) and isocyanate compound (H-). It is a general term for (meth) acrylates obtained by reaction with 2-ro).
少なくとも一つの(メタ)アクリロイルオキシ基を有するヒドロキシ化合物(H−2−イ)の具体例としては、例えば、2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシブチル(メタ)アクリレート、4−ヒドロキシエチル(メタ)アクリレート、シクロヘキサンジメタノールモノ(メタ)アクリレート、ポリエチレングリコールモノ(メタ)アクリレート、ポリプロピレングリコールモノ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、2−ヒドロキシ−3−フェノキシプロピル(メタ)アクリレートなど各種の水酸基を有する(メタ)アクリレート化合物と、上記の水酸基を有する(メタ)アクリレート化合物とε−カプロラクトンとの開環反応物などを挙げることができる。 Specific examples of the hydroxy compound (H-2-i) having at least one (meth) acryloyloxy group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 2-hydroxybutyl. (Meth) acrylate, 4-hydroxyethyl (meth) acrylate, cyclohexanedimethanol mono (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, pentaerythritol tri (meth) acrylate, 2-hydroxy Ring-opening reaction product of (meth) acrylate compound having various hydroxyl groups such as -3-phenoxypropyl (meth) acrylate, and (meth) acrylate compound having the above hydroxyl group and ε-caprolactone Etc. can be mentioned.
イソシアネート化合物(H−2−ロ)の具体例としては、例えば、P−フェニレンジイソシアネート、m−フェニレンジイソシアネート、P−キシレンジイソシアネート、m−キシレンジイソシアネート、2,4−トリレンジイソシアネート、2,6−トリレンジイソシアネート、4,4’−ジフェニルメタンジイソシアネート、ナフタレンジイソシアネートの如き芳香族ジイソシアネート類;イソホロンジイソシアネート、ヘキサメチレンジイソシアネート、4,4’−ジシクロヘキシルメタンジイソシアネート、水添キシレンジイソシアネート、ノルボルネンジイソシアネート、リジンジイソシアネート等の脂肪族又は脂環構造のジイソシアネート類;イソシアネートモノマーの一種類以上のビュレット体又は、上記ジイソシアネート化合物を3量化したイソシアネート体等のポリイソシアネート;上記イソシアネート化合物と前記、ポリオール化合物とのウレタン化反応によって得られるポリイソシアネート等を挙げることができる。 Specific examples of the isocyanate compound (H-2-ro) include, for example, P-phenylene diisocyanate, m-phenylene diisocyanate, P-xylene diisocyanate, m-xylene diisocyanate, 2,4-tolylene diisocyanate, and 2,6-triene. Aromatic diisocyanates such as diisocyanate, 4,4'-diphenylmethane diisocyanate, naphthalene diisocyanate; aliphatics such as isophorone diisocyanate, hexamethylene diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, hydrogenated xylene diisocyanate, norbornene diisocyanate, lysine diisocyanate Or diisocyanates having an alicyclic structure; one or more burettes of isocyanate monomers or the above diisocyanates Things a trimer polyisocyanates of the isocyanate and the like; the and the isocyanate compound include polyisocyanates obtained by urethane reaction of the polyol compound.
尚、ウレタン(メタ)アクリレートを得る際に(メタ)アクリロイルオキシ基を有するヒドロキシ化合物(H−2−イ)とイソシアネート化合物(H−2−ロ)との反応において、任意にポリオールを反応させても構わない。
使用できるポリオールとしては、例えば、ネオペンチルグリコール、3−メチル−1、5−ペンタンジオール、エチレングリコール、プロピレングリコール、1,4−ブタンジオール、1、6−ヘキサンジオール等の炭素数1〜10のアルキレングリコール、トリメチロールプロパン、ペンタエリスリトール等のトリオール、トリシクロデカンジメチロール、ビス−〔ヒドロキシメチル〕−シクロヘキサン等の環状骨格を有するアルコール等;及びこれら多価アルコールと多塩基酸(例えば、コハク酸、フタル酸、ヘキサヒドロ無水フタル酸、テレフタル酸、アジピン酸、アゼライン酸、テトラヒドロ無水フタル酸等)との反応によって得られるポリエステルポリオール、多価アルコールとε−カプロラクトンとの反応によって得られるカプロラクトンアルコール、ポリカーボネートポリオール(例えば1,6−ヘキサンジオールとジフェニルカーボネートとの反応によって得られるポリカーボネートジオール等)又はポリエーテルポリオール(例えばポリエチレングリコール、ポリプロピレングリコール、ポリテトラメチレングリコール、エチレンオキサイド変性ビスフェノールA等)等が挙げられる。
In the reaction of the hydroxy compound (H-2-i) having a (meth) acryloyloxy group and the isocyanate compound (H-2-ro) when obtaining urethane (meth) acrylate, a polyol is optionally reacted. It doesn't matter.
Examples of the polyol that can be used include 1 to 10 carbon atoms such as neopentyl glycol, 3-methyl-1,5-pentanediol, ethylene glycol, propylene glycol, 1,4-butanediol, and 1,6-hexanediol. Triols such as alkylene glycol, trimethylolpropane, pentaerythritol, alcohols having a cyclic skeleton such as tricyclodecane dimethylol, bis- [hydroxymethyl] -cyclohexane, and the like; and these polyhydric alcohols and polybasic acids (for example, succinic acid) , Phthalic acid, hexahydrophthalic anhydride, terephthalic acid, adipic acid, azelaic acid, tetrahydrophthalic anhydride, etc.) polyester polyol obtained by reaction with polyhydric alcohol and ε-caprolactone Lactone alcohol, polycarbonate polyol (for example, polycarbonate diol obtained by reaction of 1,6-hexanediol and diphenyl carbonate) or polyether polyol (for example, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, ethylene oxide-modified bisphenol A, etc.) Etc.
本発明の感光性樹脂組成物に併用可能エポキシ(メタ)アクリレート(H−3)は、1官能性以上のエポキシ基を含有するエポキシ樹脂と(メタ)アクリル酸とを反応させて得られる(メタ)アクリレートの総称である。エポキシ(メタ)アクリレートの原料となるエポキシ樹脂の具体例としては、ハイドロキノンジグリシジルエーテル、カテコールジグリシジルエーテル、レゾルシノールジグリシジルエーテル等のフェニルジグリシジルエーテル;ビスフェノール−A型エポキシ樹脂、ビスフェノール−F型エポキシ樹脂、ビスフェノール−S型エポキシ樹脂、2,2−ビス(4−ヒドロキシフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパンのエポキシ化合物等のビスフェノール型エポキシ化合物;水素化ビスフェノール−A型エポキシ樹脂、水素化ビスフェノール−F型エポキシ樹脂、水素化ビスフェノール−S型エポキシ樹脂、水素化2,2−ビス(4−ヒドロキシフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパンのエポキシ化合物等の水素化ビスフェノール型エポキシ化合物;臭素化ビスフェノール−A型エポキシ樹脂、臭素化ビスフェノール−F型エポキシ樹脂等のハロゲノ化ビスフェノール型エポキシ化合物;シクロヘキサンジメタノールジグリシジルエーテル化合物等の脂環式ジグリシジルエーテル化合物;1,6−ヘキサンジオールジグリシジルエーテル、1,4−ブタンジオールジグリシジルエーテル、ジエチレングリコールジグリシジルエーテル等の脂肪族ジグリシジルエーテル化合物;ポリサルファイドジグリシジルエーテル等のポリサルファイド型ジグリシジルエーテル化合物;フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、トリスヒドロキシフェニルメタン型エポキシ樹脂、ジシクロペンタジエンフェノール型エポキシ樹脂、ビフェノール型エポキシ樹脂、ビスフェノール−Aノボラック型エポキシ樹脂、ナフタレン骨格含有エポキシ樹脂、複素環式エポキシ樹脂等を挙げることができる。 The epoxy (meth) acrylate (H-3) that can be used in combination with the photosensitive resin composition of the present invention is obtained by reacting an epoxy resin containing an epoxy group having one or more functionalities with (meth) acrylic acid (meta). ) A general term for acrylate. Specific examples of epoxy resins used as raw materials for epoxy (meth) acrylates include phenyl diglycidyl ethers such as hydroquinone diglycidyl ether, catechol diglycidyl ether, resorcinol diglycidyl ether; bisphenol-A type epoxy resin, bisphenol-F type epoxy Resin, bisphenol-S type epoxy resin, bisphenol type epoxy compound such as 2,2-bis (4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane epoxy compound; hydrogenated bisphenol- A type epoxy resin, hydrogenated bisphenol-F type epoxy resin, hydrogenated bisphenol-S type epoxy resin, hydrogenated 2,2-bis (4-hydroxyphenyl) -1,1,1,3,3,3-hexa Fluoropropane Epoxy Hydrogenated bisphenol type epoxy compounds such as compounds; Halogenated bisphenol type epoxy compounds such as brominated bisphenol-A type epoxy resins and brominated bisphenol-F type epoxy resins; Alicyclic diglycidyl such as cyclohexanedimethanol diglycidyl ether compounds Ether compounds; Aliphatic diglycidyl ether compounds such as 1,6-hexanediol diglycidyl ether, 1,4-butanediol diglycidyl ether, and diethylene glycol diglycidyl ether; Polysulfide type diglycidyl ether compounds such as polysulfide diglycidyl ether; Phenol Novolac epoxy resin, cresol novolac epoxy resin, trishydroxyphenylmethane epoxy resin, dicyclopentadienephenol Epoxy resins, biphenol type epoxy resin, bisphenol -A novolac epoxy resins, naphthalene skeleton-containing epoxy resin, a heterocyclic epoxy resin or the like.
本発明の感光性樹脂組成物に併用可能な(ポリ)エーテル(メタ)アクリレート(H−4)としては、例えば、ブトキシエチル(メタ)アクリレート、ブトキシトリエチレングリコール(メタ)アクリレート、エピクロルヒドリン変性ブチル(メタ)アクリレート、ジシクロペンテニロキシエチル(メタ)アクリレート、2−エトキシエチル(メタ)アクリレート、エチルカルビトール(メタ)アクリレート、フェノキシエチル(メタ)アクリレート、ノニルフェノキシポリエチレングリコール(メタ)アクリレート等の単官能(ポリ)エーテル(メタ)アクリレート類; Examples of the (poly) ether (meth) acrylate (H-4) that can be used in combination with the photosensitive resin composition of the present invention include butoxyethyl (meth) acrylate, butoxytriethylene glycol (meth) acrylate, epichlorohydrin-modified butyl ( (Meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, ethyl carbitol (meth) acrylate, phenoxyethyl (meth) acrylate, nonylphenoxypolyethylene glycol (meth) acrylate, etc. Functional (poly) ether (meth) acrylates;
ポリエチレングリコールジ(メタ)アクリレート、ポリプロピレングリコールジ(メタ)アクリレート、ポリブチレングリコールジ(メタ)アクリレート、ポリテトラメチレングリコールジ(メタ)アクリレート等のアルキレングリコールジ(メタ)アクリレート類;エチレンオキシドとプロピレンオキシドの共重合体、プロピレングリコールとテトラヒドロフランの共重合体、ポリイソプレングリコール、水添ポリイソプレングリコール、ポリブタジエングリコール、水添ポリブタジェングリコール等の炭化水素系ポリオール類等の多価水酸基化合物と(メタ)アクリル酸から誘導される多官能(メタ)アクリレート類;ネオペンチルグリコール1モルに1モル以上のエチレンオキサイド、プロピレンオキサイド、ブチレンオキサイド等の環状エーテルを付加したジオールのジ(メタ)アクリレート; Alkylene glycol di (meth) acrylates such as polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, polybutylene glycol di (meth) acrylate, polytetramethylene glycol di (meth) acrylate; ethylene oxide and propylene oxide Copolymer, copolymer of propylene glycol and tetrahydrofuran, polyisoprene glycol, hydrogenated polyisoprene glycol, polybutadiene glycol, polyhydric hydroxyl compounds such as hydrogenated polybutadiene glycol and other polyhydric hydroxyl compounds and (meth) acrylic Polyfunctional (meth) acrylates derived from acids; 1 mole or more of ethylene oxide, propylene oxide, butylene oxide, etc. per 1 mole of neopentyl glycol Di (meth) acrylate of a diol obtained by adding Jo ether;
ビスフェノールA、ビスフェノールF、ビスフェノールS等のビスフェノール類のアルキレンオキシド変性体のジ(メタ)アクリレート;水添ビスフェノールA、水添ビスフェノールF、水添ビスフェノールS等の水添ビスフェノール類のアルキレンオキシド変性体ジ(メタ)アクリレート;トリメチロールプロパン又はグリセリン1モルに1モル以上のエチレンオキサイド、プロピレンオキサイド、ブチレンオキサイド等の環状エーテル化合物を付加して得たトリオールのモノ、ジ又はトリ(メタ)アクリレート; Di (meth) acrylates of alkylene oxide modified products of bisphenols such as bisphenol A, bisphenol F and bisphenol S; Hydrogenated bisphenols such as hydrogenated bisphenol A, hydrogenated bisphenol F and hydrogenated bisphenol S (Meth) acrylate; mono-, di- or tri (meth) acrylate of triol obtained by adding 1 mol or more of cyclic ether compound such as ethylene oxide, propylene oxide, butylene oxide to 1 mol of trimethylolpropane or glycerin;
ペンタエリスリトール又はジトリメチロールプロパン1モルに1モル以上のエチレンオキサイド、プロピレンオキサイド、ブチレンオキサイド等の環状エーテル化合物を付加したトリオールのモノ、ジ、トリ又はテトラ(メタ)アクリレート;ジペンタエリスリトール1モルに1モル以上のエチレンオキサイド、プロピレンオキサイド、ブチレンオキサイド等の環状エーテル化合物を付加したヘキサオールの3乃至6官能(メタ)アクリレート等の多官能(ポリ)エーテル(メタ)アクリレート類などを挙げることができる。 Mono-, di-, tri-, or tetra (meth) acrylates of triols obtained by adding 1 mol or more of a cyclic ether compound such as ethylene oxide, propylene oxide, butylene oxide to 1 mol of pentaerythritol or ditrimethylolpropane; 1 mol of dipentaerythritol Examples thereof include polyfunctional (poly) ether (meth) acrylates such as hexaol tri- to hexafunctional (meth) acrylates to which cyclic ether compounds such as ethylene oxide, propylene oxide, butylene oxide and the like are added in a molar amount or more.
本発明の感光性樹脂組成物に併用可能なアルキル(メタ)アクリレート又はアルキレン(メタ)アクリレート(H−5)としては、例えば、メチル(メタ)アクリレート、エチル(メタ)アクリレート、プロピル(メタ)アクリレート、n−ブチル(メタ)アクリレート、i−ブチル(メタ)アクリレート、t−ブチル(メタ)アクリレート、ヘキシル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、ラウリル(メタ)アクリレート、オクチル(メタ)アクリレート、イソオクチル(メタ)アクリレート、デシル(メタ)アクリレート、ドデシル(メタ)アクリレート、ステアリル(メタ)アクリレート、イソステアリル(メタ)アクリレート、イソボルニル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、トリメチルシクロヘキシル(メタ)アクリレート、1−アダマンチル(メタ)アクリレート、2−エチルヘキシルカルビトール(メタ)アクリレート等の単官能(メタ)アクリレート類; Examples of the alkyl (meth) acrylate or alkylene (meth) acrylate (H-5) that can be used in combination with the photosensitive resin composition of the present invention include methyl (meth) acrylate, ethyl (meth) acrylate, and propyl (meth) acrylate. , N-butyl (meth) acrylate, i-butyl (meth) acrylate, t-butyl (meth) acrylate, hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, octyl (meth) acrylate , Isooctyl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate, stearyl (meth) acrylate, isostearyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentenyl (meth) acrylate , Dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, cyclohexyl (meth) acrylate, trimethylcyclohexyl (meth) acrylate, 1-adamantyl (meth) acrylate, 2-ethylhexyl carbitol (meth) acrylate, etc. Monofunctional (meth) acrylates of
エチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、1,4−ブタンジオールジ(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、2−メチル−1,8−オクタンジオールジ(メタ)アクリレート、1,9−ノナンジオールジ(メタ)アクリレート、1,10−デカンジオールジ(メタ)アクリレートの炭化水素ジオールのジ(メタ)アクリレート類; Ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 2 -Di (meth) acrylates of hydrocarbon diols of methyl-1,8-octanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 1,10-decanediol di (meth) acrylate;
トリメチロールプロパンのモノ(メタ)アクリレート、ジ(メタ)アクリレート又はトリ(メタ)アクリレート(以下、ジ、トリ、テトラ等の多官能の総称として「ポリ」を用いる。)、グリセリンのモノ(メタ)アクリレート又はポリ(メタ)アクリレート、ペンタエリスリトールのモノ又はポリ(メタ)アクリレート、ジトリメチロールプロパンのモノ又はポリ(メタ)アクリレート、ジペンタエリスリトールのモノ又はポリ(メタ)アクリレート等のトリオール、テトラオール、ヘキサオール等の多価アルコールのモノ又はポリ(メタ)アクリレート類; Mono (meth) acrylate, di (meth) acrylate or tri (meth) acrylate of trimethylolpropane (hereinafter, “poly” is used as a general term for polyfunctionality such as di, tri, tetra, etc.), mono (meth) of glycerin Triols such as acrylate or poly (meth) acrylate, mono- or poly (meth) acrylate of pentaerythritol, mono- or poly (meth) acrylate of ditrimethylolpropane, mono- or poly (meth) acrylate of dipentaerythritol, tetraol, hexa Mono- or poly (meth) acrylates of polyhydric alcohols such as oar;
2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、4−ヒドロキシブチル(メタ)アクリレート等の水酸基含有(メタ)アクリル類;などを挙げることができる。 And hydroxyl group-containing (meth) acrylic compounds such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
本発明の感光性樹脂組成物に併用可能な芳香環を有する(メタ)アクリレート(H−6)としては、例えば、フェニル(メタ)アクリレート、ベンジル(メタ)アクリレート等の単官能(メタ)アクリレート類;ビスフェノールAジ(メタ)アクリレート、ビスフェノールFジ(メタ)アクリレート等のジ(メタ)アクリレート類等を挙げることができるが、これらに限定されるものではない。 Examples of the (meth) acrylate (H-6) having an aromatic ring that can be used in combination with the photosensitive resin composition of the present invention include monofunctional (meth) acrylates such as phenyl (meth) acrylate and benzyl (meth) acrylate. And di (meth) acrylates such as bisphenol A di (meth) acrylate and bisphenol F di (meth) acrylate, but are not limited thereto.
本発明の感光性樹脂組成物に併用可能な脂環構造を有する(メタ)アクリレート(H−7)としては、例えば、シクロヘキシル(メタ)アクリレート、シクロペンチル(メタ)アクリレート、イソボルニル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレート等の脂環構造を有する単官能(メタ)アクリレート類;水添ビスフェノールA、水添ビスフェノールF等の水添ビスフェノール類のジ(メタ)アクリレート;トリシクロデカンジメチロールジ(メタ)アクリレート等の環状構造を持つ多官能性(メタ)アクリレート類;テトラフルフリル(メタ)アクリレート等の構造中に酸素原子等を有する脂環式(メタ)アクリレート、などを挙げることができるが、これらに限定されるものではない。 Examples of the (meth) acrylate (H-7) having an alicyclic structure that can be used in combination with the photosensitive resin composition of the present invention include cyclohexyl (meth) acrylate, cyclopentyl (meth) acrylate, isobornyl (meth) acrylate, and di Monofunctional (meth) acrylates having an alicyclic structure such as cyclopentenyl (meth) acrylate; di (meth) acrylates of hydrogenated bisphenols such as hydrogenated bisphenol A and hydrogenated bisphenol F; tricyclodecane dimethylol di ( Examples thereof include polyfunctional (meth) acrylates having a cyclic structure such as (meth) acrylate; alicyclic (meth) acrylates having an oxygen atom or the like in the structure such as tetrafurfuryl (meth) acrylate. However, it is not limited to these.
また、本発明の感光性樹脂組成物に併用可能な(メタ)アクリロイル基を有する化合物としては、上記した化合物の他に、例えば、(メタ)アクリル酸ポリマーとグリシジル(メタ)アクリレートとの反応物又はグリシジル(メタ)アクリレートポリマーと(メタ)アクリル酸との反応物等のポリ(メタ)アクリルポリマー(メタ)アクリレート;ジメチルアミノエチル(メタ)アクリレート等のアミノ基を有する(メタ)アクリレート;トリス(メタ)アクリロキシエチルイソシアヌレート等のイソシアヌル(メタ)アクリレート;ポリシロキサン骨格を有する(メタ)アクリレート;ポリブタジェン(メタ)アクリレート、メラミン(メタ)アクリレート等も使用可能である。 Examples of the compound having a (meth) acryloyl group that can be used in combination with the photosensitive resin composition of the present invention include, for example, a reaction product of a (meth) acrylic acid polymer and glycidyl (meth) acrylate, in addition to the above-described compounds. Or a poly (meth) acrylic polymer (meth) acrylate such as a reaction product of a glycidyl (meth) acrylate polymer and (meth) acrylic acid; a (meth) acrylate having an amino group such as dimethylaminoethyl (meth) acrylate; Isocyanuric (meth) acrylates such as (meth) acryloxyethyl isocyanurate; (meth) acrylates having a polysiloxane skeleton; polybutadiene (meth) acrylates, melamine (meth) acrylates, and the like can also be used.
また、本発明の感光性樹脂組成物に併用可能なマレイミド基含有化合物(H−8)としては、例えば、N−n−ブチルマレイミド、N−ヘキシルマレイミド、2−マレイミドエチル−エチルカーボネート、2−マレイミドエチル−プロピルカーボネート、N−エチル−(2−マレイミドエチル)カーバメート等の単官能脂肪族マレイミド類;N−シクロヘキシルマレイミド等の脂環式単官能マレイミド類;N、N−ヘキサメチレンビスマレイミド、ポリプロピレングリコール−ビス(3−マレイミドプロピル)エーテル、ビス(2−マレイミドエチル)カーボネート等の脂肪族ビスマレイミド類;1,4−ジマレイミドシクロヘキサン、イソホロンビスウレタンビス(N−エチルマレイミド)等の脂環式ビスマレイミド;マレイミド酢酸とポリテトラメチレングリコールとをエステル化して得られるマレイミド化合物、マレイミドカプロン酸とペンタエリスリトールのテトラエチレンオキサイド付加物とのエステル化によるマレイミド化合物等のカルボキシマレイミド誘導体と種々の(ポリ)オールとをエステル化して得られる(ポリ)エステル(ポリ)マレイミド化合物等を挙げることができるが、これらに限定されるものではない。 Examples of the maleimide group-containing compound (H-8) that can be used in combination with the photosensitive resin composition of the present invention include Nn-butylmaleimide, N-hexylmaleimide, 2-maleimidoethyl-ethyl carbonate, 2- Monofunctional aliphatic maleimides such as maleimidoethyl-propyl carbonate and N-ethyl- (2-maleimidoethyl) carbamate; Alicyclic monofunctional maleimides such as N-cyclohexylmaleimide; N, N-hexamethylene bismaleimide, polypropylene Aliphatic bismaleimides such as glycol-bis (3-maleimidopropyl) ether and bis (2-maleimidoethyl) carbonate; cycloaliphatic such as 1,4-dimaleimidocyclohexane and isophorone bisurethane bis (N-ethylmaleimide) Bismaleimide; maleimidoacetic acid and poly Obtained by esterification of carboxymaleimide derivatives such as maleimide compounds obtained by esterification with tetramethylene glycol, maleimide compounds by maleification of maleimidocaproic acid and pentaerythritol tetraethylene oxide adducts, and various (poly) ols. (Poly) ester (poly) maleimide compounds and the like that can be used can be mentioned, but are not limited thereto.
本発明の感光性樹脂組成物に併用可能な(メタ)アクリルアミド化合物(H−9)としては、例えば、アクリロイルモルホリン、N−イソプロピル(メタ)アクリルアミド等の単官能性(メタ)アクリルアミド類;メチレンビス(メタ)アクリルアミド等の多官能(メタ)アクリルアミド類などを挙げることができる。 Examples of the (meth) acrylamide compound (H-9) that can be used in combination with the photosensitive resin composition of the present invention include monofunctional (meth) acrylamides such as acryloylmorpholine and N-isopropyl (meth) acrylamide; Examples thereof include polyfunctional (meth) acrylamides such as (meth) acrylamide.
本発明の感光性樹脂組成物に併用可能な不飽和ポリエステル(H−10)としては、例えば、ジメチルマレート、ジエチルマレート等のフマル酸エステル類;マレイン酸、フマル酸等の多価不飽和カルボン酸と多価アルコールとのエステル化反応物を挙げることができる。 Examples of the unsaturated polyester (H-10) that can be used in combination with the photosensitive resin composition of the present invention include fumaric acid esters such as dimethyl malate and diethyl malate; polyunsaturated such as maleic acid and fumaric acid. The esterification reaction product of carboxylic acid and a polyhydric alcohol can be mentioned.
本発明の感光性樹脂組成物に併用可能な重合性化合物(H)は、低粘度で耐光性、作業性に優れたアルキル(メタ)アクリレート又はアルキレン(メタ)アクリレート(H−5)の併用が好ましいが、上記した化合物に限定されたものではなく、前記(E)、(F)成分と共重合性を有する化合物であれば、その1種類又は複数種の化合物を、特に制限なく、併用することができる。
中でも、アルキル(メタ)アクリレート又はアルキレン(メタ)アクリレート等でC5〜C35、より好ましくはC15〜C35の長鎖を有する(メタ)アクリロイルオキシ基を有する化合物が好適である。このような構造を有することで、相溶性及び透明性に優れた感光性樹脂組成物を得ることができるためである。
The polymerizable compound (H) that can be used in combination with the photosensitive resin composition of the present invention is a combination of alkyl (meth) acrylate or alkylene (meth) acrylate (H-5) that has low viscosity, excellent light resistance, and workability. Although it is preferable, the compound is not limited to the above-described compounds, and one or a plurality of compounds are used in combination without particular limitation as long as the compounds have copolymerizability with the components (E) and (F). be able to.
Among them, a compound having a (meth) acryloyloxy group having a long chain of C5 to C35, more preferably C15 to C35, such as alkyl (meth) acrylate or alkylene (meth) acrylate is preferable. This is because a photosensitive resin composition having excellent compatibility and transparency can be obtained by having such a structure.
本発明の感光性樹脂組成物において、前記(E)、(F)及び(H)成分の割合としては、特に制限がないが、(E)成分100重量%に対して、(F)成分を10〜2000重量%、(H)成分を10〜2000重量%を含有するのが好ましく、(F)成分を20〜1000重量%、(H)成分を20〜1000重量%を含有するのが特に好ましい。 In the photosensitive resin composition of the present invention, the ratio of the components (E), (F) and (H) is not particularly limited, but the component (F) is added to 100% by weight of the component (E). It is preferable to contain 10 to 2000% by weight of the component (H), and 10 to 2000% by weight of the component (H), particularly 20 to 1000% by weight of the component (F) and 20 to 1000% by weight of the component (H). preferable.
本発明の感光性樹脂組成物に用いられる光重合開始剤(I)の具体例としては、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインプロピルエーテル、ベンゾインイソブチルエーテル等のベンゾイン類;アセトフェノン、2,2−ジエトキシ−2−フェニルアセトフェノン、1,1−ジクロロアセトフェノン、2−ヒドロキシ−2−メチル−フェニルプロパン−1−オン、ジエトキシアセトフェノン、1−ヒドロキシクロヘキシルフェニルケトン、2−メチル−1−〔4−(メチルチオ)フェニル〕−2−モルホリノプロパン−1−オンなどのアセトフェノン類;2−エチルアントラキノン、2−ターシャリーブチルアントラキノン、2−クロロアントラキノン、2−アミルアントラキノンなどのアントラキノン類;2,4−ジエチルチオキサントン、2−イソプロピルチオキサントン、2−クロロチオキサントンなどのチオキサントン類;アセトフエノンジメチルケタール、ベンジルジメチルケタールなどのケタール類;ベンゾフェノン、4−ベンゾイル−4'−メチルジフェニルサルファイド、4,4'−ビスメチルアミノベンゾフェノンなどのベンゾフェノン類;2,4,6−トリメチルベンゾイルジフェニルホスフィンオキサイド、ビス(2,4,6−トリメチルベンゾイル)−フェニルホスフィンオキサイド等のホスフィンオキサイド類等が挙げられる。これらの添加割合としては、感光性樹脂組成物の固形分を100重量%としたとき、通常0.01〜30重量%、好ましくは、0.1〜25重量%である。 Specific examples of the photopolymerization initiator (I) used in the photosensitive resin composition of the present invention include benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, and benzoin isobutyl ether; acetophenone, 2, 2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 2-hydroxy-2-methyl-phenylpropan-1-one, diethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4 Acetophenones such as-(methylthio) phenyl] -2-morpholinopropan-1-one; anthraquino such as 2-ethylanthraquinone, 2-tertiarybutylanthraquinone, 2-chloroanthraquinone, 2-amylanthraquinone Thioxanthones such as 2,4-diethylthioxanthone, 2-isopropylthioxanthone, 2-chlorothioxanthone; ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; benzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, Benzophenones such as 4,4′-bismethylaminobenzophenone; phosphine oxides such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide . The addition ratio of these is usually 0.01 to 30% by weight, preferably 0.1 to 25% by weight, when the solid content of the photosensitive resin composition is 100% by weight.
これらは、単独または2種以上の混合物として使用でき、さらにはトリエタノールアミン、メチルジエタノールアミンなどの第3級アミン、N,N−ジメチルアミノ安息香酸エチルエステル、N,N−ジメチルアミノ安息香酸イソアミルエステル等の安息香酸誘導体等の促進剤などと組み合わせて使用することができる。これらの促進剤の添加量としては、光重合開始剤(I)に対して、100重量%以下となる量を必要に応じて添加する。 These can be used singly or as a mixture of two or more, and further, tertiary amines such as triethanolamine and methyldiethanolamine, N, N-dimethylaminobenzoic acid ethyl ester, N, N-dimethylaminobenzoic acid isoamyl ester Can be used in combination with an accelerator such as a benzoic acid derivative. As an addition amount of these accelerators, an amount of 100% by weight or less is added to the photopolymerization initiator (I) as necessary.
更に、本発明の感光性樹脂組成物は、用途に応じて、非反応性化合物、無機充填剤、有機充填剤、シランカップリング剤、粘着付与剤、消泡剤、レベリング剤、可塑剤、酸化防止剤、紫外線吸収剤、難燃剤、顔料、染料等を適宜使用することができる。 Furthermore, the photosensitive resin composition of the present invention is a non-reactive compound, an inorganic filler, an organic filler, a silane coupling agent, a tackifier, an antifoaming agent, a leveling agent, a plasticizer, an oxidation, depending on the application. Inhibitors, ultraviolet absorbers, flame retardants, pigments, dyes, and the like can be used as appropriate.
前記、非反応性化合物の具体例としては、反応性の低い、或いは反応性の無い液状若しくは固体状のオリゴマーや樹脂であり、(メタ)アクリル酸アルキル共重合体、エポキシ樹脂、液状ポリブタジェン、ジシクロペンタジェン誘導体、飽和ポリエステルオリゴマー、キシレン樹脂、ポリウレタンポリマー、ケトン樹脂、ジアリルフタレートポリマー(ダップ樹脂)、石油樹脂、ロジン樹脂、フッ素系オリゴマー、シリコン系オリゴマー、フタル酸エステル類、リン酸エステル類、グリコールエステル類、クエン酸エステル類、脂肪族二塩基酸エステル類、脂肪酸エステル類、エポキシ系可塑剤、ヒマシ油類、テルペン系水素添加樹脂ポリイソプレン骨格、ポリブタジエン骨格又はキシレン骨格を有するオリゴマー又はポリマー及びそのエステル化物、ブタジエンホモポリマー、エポキシ変性ポリブタジエン、ブタジエン−スチレンランダムコポリマー、ポリブテン、等の柔軟化剤などを挙げることができるが、これらに限定されるものではない。かかる成分の紫外線硬化型樹脂組成物中における重量割合は、通常10〜80重量%、好ましくは10〜70重量%である。 Specific examples of the non-reactive compound include a liquid or solid oligomer or resin having low reactivity or non-reactivity, and includes an alkyl (meth) acrylate copolymer, an epoxy resin, liquid polybutadiene, Cyclopentagen derivatives, saturated polyester oligomers, xylene resins, polyurethane polymers, ketone resins, diallyl phthalate polymers (dup resins), petroleum resins, rosin resins, fluorine-based oligomers, silicon-based oligomers, phthalate esters, phosphate esters, Glycol esters, citric acid esters, aliphatic dibasic acid esters, fatty acid esters, epoxy plasticizers, castor oils, terpene hydrogenated resin polyisoprene skeletons, oligomers or polymers having polybutadiene skeletons or xylene skeletons, and That S Le product, homopolymer, epoxy-modified polybutadiene, butadiene - styrene random copolymer, polybutene, and the like can be mentioned softening agents etc., but is not limited thereto. The weight ratio of such components in the ultraviolet curable resin composition is usually 10 to 80% by weight, preferably 10 to 70% by weight.
前記、無機充填剤としては、例えば、二酸化珪素、酸化珪素、炭酸カルシウム、珪酸カルシウム、炭酸マグネシウム、酸化マグネシウム、タルク、カオリンクレー、焼成クレー、酸化亜鉛、硫酸亜鉛、水酸アルミニウム、酸化アルミニウム、ガラス、雲母、硫酸バリウム、アルミナホワイト、ゼオライト、シリカバルーン、ガラスバルーン、等を挙げることができる。これらの無機充填剤には、シランカップリング剤、チタネート系カップリング剤、アルミニウム系カップリング剤、ジルコネート系カップリング剤などを添加、反応させるなどの方法により、ハロゲン基、エポキシ基、水酸基、チオール基の官能基を持たせることもできる。 Examples of the inorganic filler include silicon dioxide, silicon oxide, calcium carbonate, calcium silicate, magnesium carbonate, magnesium oxide, talc, kaolin clay, calcined clay, zinc oxide, zinc sulfate, aluminum hydroxide, aluminum oxide, and glass. , Mica, barium sulfate, alumina white, zeolite, silica balloon, glass balloon, and the like. These inorganic fillers may be added with a silane coupling agent, titanate coupling agent, aluminum coupling agent, zirconate coupling agent, or the like, and reacted to form a halogen group, an epoxy group, a hydroxyl group, or a thiol. It can also have a functional group.
前記、有機充填剤としては、例えば、ベンゾグアナミン樹脂、シリコーン樹脂、低密度ポリエチレン、高密度ポリエチレン、ポリオレフィン樹脂、エチレン・アクリル酸共重合体、ポリスチレン、アクリル共重合体、ポリメチルメタクリレート樹脂、フッ素樹脂、ナイロン12、ナイロン6/66、フェノール樹脂、エポキシ樹脂、ウレタン樹脂、ポリイミド樹脂などを挙げることができる。 Examples of the organic filler include benzoguanamine resin, silicone resin, low density polyethylene, high density polyethylene, polyolefin resin, ethylene / acrylic acid copolymer, polystyrene, acrylic copolymer, polymethyl methacrylate resin, fluororesin, Nylon 12, nylon 6/66, phenol resin, epoxy resin, urethane resin, polyimide resin and the like can be mentioned.
シランカップリング剤としては、例えば、γ−グリシドキシプロピルトレメトキシシラン又はγ−クロロプロピルトリメトキシシラン等のシランカップリング剤、テトラ(2,2−ジアリルオキシメチル−1−ブチル)ビス(ジトリデシル)ホスファイトチタネート、ビス(ジオクチルパイロホスフェート)エチレンチタネート等のチタネート系カップリング剤;アセトアルコキシアルミニウムジイソプロピレート等のアルミニウム系カップリング剤;アセチルアセトン・ジルコニウム錯体等のジルコニウム系カップリング剤、などを挙げることができる。 Examples of the silane coupling agent include silane coupling agents such as γ-glycidoxypropyl tremethoxysilane and γ-chloropropyltrimethoxysilane, and tetra (2,2-diallyloxymethyl-1-butyl) bis (ditridecyl). ) Titanate coupling agents such as phosphite titanate and bis (dioctylpyrophosphate) ethylene titanate; Aluminum coupling agents such as acetoalkoxyaluminum diisopropylate; Zirconium coupling agents such as acetylacetone / zirconium complex, etc. be able to.
本発明の感光性樹脂組成物に使用可能な粘着付与剤、消泡剤、レベリング剤、可塑剤、酸化防止剤、紫外線吸収剤、難燃剤、顔料及び染料は、公知慣用のものであれば如何なるものも、その硬化性、樹脂特性を損なわない範囲で、特に制限無く使用することができる。 Any tackifier, antifoaming agent, leveling agent, plasticizer, antioxidant, ultraviolet absorber, flame retardant, pigment, and dye that can be used in the photosensitive resin composition of the present invention can be used. In the range which does not impair the sclerosis | hardenability and resin characteristic, a thing can be especially used without a restriction | limiting.
本発明の感光性樹脂組成物を得るには、上記した各成分を混合すればよく、混合の順序や方法は特に限定されない。
各種添加剤の組成物中に存在する場合、各種添加剤の光硬化型透明接着剤組成物中における重量割合は、0.01〜3重量%、好ましくは0.01〜1重量%、より好ましくは0.02〜0.5重量%である。
In order to obtain the photosensitive resin composition of the present invention, the above-described components may be mixed, and the order and method of mixing are not particularly limited.
When present in the composition of various additives, the weight ratio of the various additives in the photocurable transparent adhesive composition is 0.01 to 3% by weight, preferably 0.01 to 1% by weight, and more preferably. Is 0.02 to 0.5% by weight.
本発明の感光性樹脂組成物は、実質的には溶剤を必要としないが、例えば、メチルエチルケトン、メチルイソブチルケトン等のケトン類、酢酸エチル、酢酸ブチル等の酢酸エステル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素など、その他の一般によく用いられる有機溶剤によって本発明の感光性樹脂組成物を希釈して使用することも可能である。 The photosensitive resin composition of the present invention does not substantially require a solvent. For example, ketones such as methyl ethyl ketone and methyl isobutyl ketone, acetates such as ethyl acetate and butyl acetate, benzene, toluene, xylene and the like It is also possible to dilute and use the photosensitive resin composition of the present invention with other generally used organic solvents such as aromatic hydrocarbons.
本発明の感光性樹脂組成物は、180〜500nmの波長の紫外線又は可視光線を照射することによって重合させることができる。又、紫外線以外のエネルギー線の照射によって、あるいは、熱によっても硬化させることができる。 The photosensitive resin composition of the present invention can be polymerized by irradiation with ultraviolet rays or visible rays having a wavelength of 180 to 500 nm. Further, it can be cured by irradiation with energy rays other than ultraviolet rays or by heat.
波長180〜500nmの紫外線又は可視光線の光発生源としては、例えば、低圧水銀ランプ、高圧水銀ランプ、超高圧水銀ランプ、メタルハライドランプ、ケミカルランプ、ブラックライトランプ、水銀−キセノンランプ、エキシマーランプ、ショートアーク灯、ヘリウム・カドミニウムレーザー、アルゴンレーザー、エキシマーレーザー、太陽光を挙げることができる。 Examples of the light generation source of ultraviolet light or visible light having a wavelength of 180 to 500 nm include, for example, a low pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a metal halide lamp, a chemical lamp, a black light lamp, a mercury-xenon lamp, an excimer lamp, and a short. Examples include arc lamps, helium / cadmium lasers, argon lasers, excimer lasers, and sunlight.
本発明の感光性樹脂組成物は、柔軟性に優れ、耐候性、耐光性が高く、透明性の維持が必要である光学用途以外にも、インキ、プラスチック塗料、紙印刷、金属コーティング、家具の塗装など種々のコーティング分野、ライニング、接着剤、更にはエレクトロニクス分野における絶縁ワニス、絶縁シート、積層板、プリント基板、レジストインキ、半導体封止剤などの多くの分野に有用である。更に具体的な用途としては、平凸版インキ、フレキソインキ、グラビアインキ、スクリーンインキなどのインキ分野、ツヤニス分野、紙塗工剤分野、木工用塗料分野、飲料缶用塗工剤又は印刷インキ分野、軟包装フィルム塗工剤、印刷インキ又は粘着剤、感熱紙、感熱フィルム用塗工剤、印刷インキ、接着剤、粘着剤又は光ファイバーコート剤、液晶表示装置、有機EL表示装置、タッチパネル型画像表示装置等の表示装置のエアギャップ充填剤(表示装置と表面板とのギャップの充填剤)などの用途に有用である。 The photosensitive resin composition of the present invention is excellent in flexibility, weather resistance, light resistance, and optical applications that need to maintain transparency, as well as ink, plastic paint, paper printing, metal coating, furniture It is useful in many fields such as various coating fields such as painting, linings, adhesives, and insulating varnishes, insulating sheets, laminates, printed boards, resist inks, and semiconductor encapsulants in the electronics field. More specific applications include planographic relief inks, flexographic inks, gravure inks, screen inks and other ink fields, glossy fields, paper coating materials fields, wood coating materials fields, beverage can coating materials or printing ink fields, Soft packaging film coating agent, printing ink or adhesive, thermal paper, thermal film coating agent, printing ink, adhesive, adhesive or optical fiber coating agent, liquid crystal display device, organic EL display device, touch panel type image display device It is useful for applications such as air gap fillers for display devices (fillers for gaps between display devices and face plates).
以下、本発明を実施例により更に具体的に説明するが、本発明が下記実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention further more concretely, this invention is not limited to the following Example.
合成例1
還流冷却器、攪拌機、温度計、温度調節装置を備えた反応器に、水添ポリブタジエンポリオール化合物として日本曹達(株)製GI−2000(ヨウ素価:12.2、水酸基価:46.8mg・KOH/g)を569.73g(0.24mol)、ジオール化合物として旭硝子(株)製エクセノール3020(ポリプロピレングリコール、水酸基価:35.9mg・KOH/g)を7.50g(0.0024mol)、重合性化合物として新中村化学(株)製S−1800A(イソステアリルアクリレート)を171.49g、重合禁止剤として4−メトキシフェノールを0.41gを添加し均一になるまで攪拌し、内部温度を50℃とした。続いてポリイソシアネート化合物としてイソホロンジイソシアネートを80.03g(0.36mol)を添加し80℃で目標のNCO含有量に達するまで反応させた。次に、少なくとも1つ以上の水酸基を有する(メタ)アクリレート化合物として大阪有機化学工業(株)製2−ヒドロキシエチルアクリレートを28.70g(0.247mol)、ウレタン化反応触媒としてオクチル酸スズを0.20gを添加し、80℃で反応させ、NCO含有量が0.1%以下となったところを反応の終点とし、ポリウレタン化合物(E−1)を得た。
Synthesis example 1
GI-2000 manufactured by Nippon Soda Co., Ltd. (iodine value: 12.2, hydroxyl value: 46.8 mg · KOH) as a hydrogenated polybutadiene polyol compound was added to a reactor equipped with a reflux condenser, a stirrer, a thermometer, and a temperature controller. / G) is 569.73 g (0.24 mol), 7.50 g (0.0024 mol) of Exenol 3020 (polypropylene glycol, hydroxyl value: 35.9 mg · KOH / g) manufactured by Asahi Glass Co., Ltd. as a diol compound is polymerizable. 171.49 g of S-1800A (isostearyl acrylate) manufactured by Shin-Nakamura Chemical Co., Ltd. as a compound and 0.41 g of 4-methoxyphenol as a polymerization inhibitor were added and stirred until uniform, and the internal temperature was 50 ° C. did. Subsequently, 80.03 g (0.36 mol) of isophorone diisocyanate was added as a polyisocyanate compound and reacted at 80 ° C. until the target NCO content was reached. Next, 28.70 g (0.247 mol) of 2-hydroxyethyl acrylate manufactured by Osaka Organic Chemical Industry Co., Ltd. is used as the (meth) acrylate compound having at least one hydroxyl group, and 0 octylate tin is used as the urethanization reaction catalyst. .20 g was added and reacted at 80 ° C., and the point where the NCO content was 0.1% or less was set as the end point of the reaction, to obtain a polyurethane compound (E-1).
合成例2
還流冷却器、攪拌機、温度計、温度調節装置を備えた反応器に、水添ポリブタジエンポリオール化合物として日本曹達(株)製GI−2000(ヨウ素価:12.2、水酸基価:46.8mg・KOH/g)を545.99g(0.23mol)、ジオール化合物として旭硝子(株)製エクセノール3020(ポリプロピレングリコール、水酸基価:35.9mg・KOH/g)を7.19g(0.0023mol)、重合性化合物として新中村化学(株)製S−1800A(イソステアリルアクリレート)を208.51g、重合禁止剤として4−メトキシフェノールを0.37gを添加し均一になるまで攪拌し、内部温度を50℃とした。続いてポリイソシアネート化合物としてイソホロンジイソシアネートを61.35g(0.28mol)を添加し80℃で目標のNCO含有量に達するまで反応させた。次に、少なくとも1つ以上の水酸基を有する(メタ)アクリレート化合物として大阪有機化学工業(株)製2−ヒドロキシエチルアクリレートを11.00g(0.095mol)、ウレタン化反応触媒としてオクチル酸スズを0.20gを添加し、80℃で反応させ、NCO含有量が0.1%以下となったところを反応の終点とし、ポリウレタン化合物(E−2)を得た。
Synthesis example 2
GI-2000 manufactured by Nippon Soda Co., Ltd. (iodine value: 12.2, hydroxyl value: 46.8 mg · KOH) as a hydrogenated polybutadiene polyol compound was added to a reactor equipped with a reflux condenser, a stirrer, a thermometer, and a temperature controller. / G) is 545.99 g (0.23 mol), 7.19 g (0.0023 mol) of Exenol 3020 (polypropylene glycol, hydroxyl value: 35.9 mg · KOH / g) manufactured by Asahi Glass Co., Ltd. as a diol compound is polymerizable. 208.51 g of S-1800A (isostearyl acrylate) manufactured by Shin-Nakamura Chemical Co., Ltd. as a compound and 0.37 g of 4-methoxyphenol as a polymerization inhibitor were added and stirred until uniform, and the internal temperature was 50 ° C. did. Subsequently, 61.35 g (0.28 mol) of isophorone diisocyanate was added as a polyisocyanate compound and reacted at 80 ° C. until the target NCO content was reached. Next, 11.00 g (0.095 mol) of 2-hydroxyethyl acrylate manufactured by Osaka Organic Chemical Industry Co., Ltd. is used as the (meth) acrylate compound having at least one hydroxyl group, and 0 octylate is used as the urethanization reaction catalyst. .20 g was added and reacted at 80 ° C., and the point where the NCO content became 0.1% or less was set as the end point of the reaction to obtain a polyurethane compound (E-2).
合成例3
還流冷却器、攪拌機、温度計、温度調節装置を備えた反応器に、水添ポリブタジエンポリオール化合物としてCRAY VALLEY製KRASOL HLBH−P 2000(ヨウ素価:13.5、水酸基価:0.89meq/g)を511.69g(0.23mol)、ジオール化合物として旭硝子(株)製エクセノール3020(ポリプロピレングリコール、水酸基価:35.9mg・KOH/g)を7.19g(0.0023mol)、重合性化合物として新中村化学(株)製S−1800A(イソステアリルアクリレート)を197.08g、重合禁止剤として4−メトキシフェノールを0.36gを添加し均一になるまで攪拌し、内部温度を50℃とした。続いてポリイソシアネート化合物としてイソホロンジイソシアネートを61.35g(0.28mol)を添加し80℃で目標のNCO含有量に達するまで反応させた。次に、少なくとも1つ以上の水酸基を有する(メタ)アクリレート化合物として大阪有機化学工業(株)製2−ヒドロキシエチルアクリレートを11.00g(0.095mol)、ウレタン化反応触媒としてオクチル酸スズを0.20gを添加し、80℃で反応させ、NCO含有量が0.1%以下となったところを反応の終点とし、ポリウレタン化合物(E−3)を得た。
Synthesis example 3
In a reactor equipped with a reflux condenser, a stirrer, a thermometer, and a temperature control device, as a hydrogenated polybutadiene polyol compound, KRASOL HLBH-P 2000 (iodine value: 13.5, hydroxyl value: 0.89 meq / g) manufactured by CRAY VALEY 511.69 g (0.23 mol), 7.19 g (0.0023 mol) of Exenol 3020 (polypropylene glycol, hydroxyl value: 35.9 mg · KOH / g) manufactured by Asahi Glass Co., Ltd. as a diol compound, and a new polymerizable compound 197.08 g of S-1800A (isostearyl acrylate) manufactured by Nakamura Chemical Co., Ltd. and 0.36 g of 4-methoxyphenol as a polymerization inhibitor were added and stirred until uniform, and the internal temperature was adjusted to 50 ° C. Subsequently, 61.35 g (0.28 mol) of isophorone diisocyanate was added as a polyisocyanate compound and reacted at 80 ° C. until the target NCO content was reached. Next, 11.00 g (0.095 mol) of 2-hydroxyethyl acrylate manufactured by Osaka Organic Chemical Industry Co., Ltd. is used as the (meth) acrylate compound having at least one hydroxyl group, and 0 octylate is used as the urethanization reaction catalyst. .20 g was added and reacted at 80 ° C., and the point where the NCO content became 0.1% or less was set as the end point of the reaction to obtain a polyurethane compound (E-3).
合成例4
水分離器、還流冷却器、攪拌機、温度計、温度調節装置を備えた反応器に、水添ポリブタジエンポリオール化合物として日本曹達(株)製GI−2000(ヨウ素価:12.2、水酸基価:46.8mg・KOH/g)を239.8g(0.10mol)、アクリル酸を21.6g(0.30mol)、溶媒としてトルエンを130.7g、重合禁止剤としてハイドロキノンを0.2g、酸触媒としてメタンスルホン酸を0.6g添加し、均一なになるまで混合攪拌した。攪拌しながら加温し、還流下で16時間反応させ生成水が流出しないことを確認し反応終了とした。得られた溶液にトルエン400g、10%NaOH400gで中和分液処理し、次いで水洗分液操作を3回実施した。得られた有機層を濃縮し溶媒留去することで、アクリル酸エステル化合物(F−1)を224g得た。
Synthesis example 4
GI-2000 manufactured by Nippon Soda Co., Ltd. (iodine value: 12.2, hydroxyl value: 46) as a hydrogenated polybutadiene polyol compound in a reactor equipped with a water separator, reflux condenser, stirrer, thermometer, and temperature control device. .8 mg · KOH / g) 239.8 g (0.10 mol), acrylic acid 21.6 g (0.30 mol), toluene 130.7 g as solvent, hydroquinone 0.2 g as polymerization inhibitor, acid catalyst 0.6 g of methanesulfonic acid was added and mixed and stirred until uniform. The mixture was heated with stirring and reacted for 16 hours under reflux to confirm that the produced water did not flow out and the reaction was completed. The resulting solution was neutralized and separated with 400 g of toluene and 400 g of 10% NaOH, and then washed with water three times. The obtained organic layer was concentrated and the solvent was distilled off to obtain 224 g of an acrylate compound (F-1).
配合例1
合成例1のポリウレタン化合物(E−1)15質量部、合成例4のアクリル酸エステル化合物(F−1)5質量部、新中村化学(株)製S−1800A(イソステアリルアクリレート)19質量部、日油(株)製ブレンマーLA(ラウリルアクリレート)10質量部、ヤスハラケミカル(株)製クリアロンM−105(芳香族変性水添テルペン樹脂)18質量部、JX日鉱日石エネルギー(株)製LV−100(ポリブテン)10質量部、日本曹達(株)製GI−2000(1,2−水素化ポリブタジエングリコール)20質量部、大阪有機化学工業(株)製4−HBA(4−ヒドロキシブチルアクリレート)3質量部、LAMBSON社製スピードキュアTPO(2,4,6−トリメチルベンゾイルジフェニルフォスフィンオキサイド)0.5質量部、BASF社製IRGACURE184(1−ヒドロキシシクロヘキシルフェニルケトン)0.5質量部を70℃に加温、混合し、本発明の感光性樹脂組成物を得た。この感光性樹脂組成物の粘度は3500mPa・sであった。
Formulation Example 1
15 parts by mass of the polyurethane compound (E-1) of Synthesis Example 1, 5 parts by mass of the acrylic ester compound (F-1) of Synthesis Example 4, 19 parts by mass of S-1800A (isostearyl acrylate) manufactured by Shin-Nakamura Chemical Co., Ltd. , 10 parts by mass of Bremer LA (lauryl acrylate) manufactured by NOF Corporation, 18 parts by mass of CLEARON M-105 (aromatic modified hydrogenated terpene resin) manufactured by Yashara Chemical Co., Ltd., LV- manufactured by JX Nippon Oil & Energy Corporation 10 parts by mass of 100 (polybutene), 20 parts by mass of GI-2000 (1,2-hydrogenated polybutadiene glycol) manufactured by Nippon Soda Co., Ltd., 4-HBA (4-hydroxybutyl acrylate) 3 manufactured by Osaka Organic Chemical Industry Co., Ltd. Part by mass, 0.5 part by mass of LAMBSON speed cure TPO (2,4,6-trimethylbenzoyldiphenylphosphine oxide), B ASF IRGACURE184 (1-hydroxycyclohexyl phenyl ketone) 0.5 part by mass was heated to 70 ° C. and mixed to obtain a photosensitive resin composition of the present invention. The viscosity of this photosensitive resin composition was 3500 mPa · s.
配合例2
合成例2のポリウレタン化合物(E−2)15質量部、合成例4のアクリル酸エステル化合物(F−1)5質量部、新中村化学(株)製S−1800A(イソステアリルアクリレート)19質量部、日油(株)製ブレンマーLA(ラウリルアクリレート)10質量部、ヤスハラケミカル(株)製クリアロンM−105(芳香族変性水添テルペン樹脂)18質量部、JX日鉱日石エネルギー(株)製LV−100(ポリブテン)10質量部、日本曹達(株)製GI−2000(1,2−水素化ポリブタジエングリコール)20質量部、大阪有機化学工業(株)製4−HBA(4−ヒドロキシブチルアクリレート)3質量部、LAMBSON社製スピードキュアTPO(2,4,6−トリメチルベンゾイルジフェニルフォスフィンオキサイド)0.5質量部、BASF社製IRGACURE184(1−ヒドロキシシクロヘキシルフェニルケトン)0.5質量部を70℃に加温、混合し、本発明の感光性樹脂組成物を得た。この感光性樹脂組成物の粘度は4600mPa・sであった。
Formulation Example 2
15 parts by mass of the polyurethane compound (E-2) of Synthesis Example 2, 5 parts by mass of the acrylate compound (F-1) of Synthesis Example 4, 19 parts by mass of S-1800A (isostearyl acrylate) manufactured by Shin-Nakamura Chemical Co., Ltd. , 10 parts by mass of Bremer LA (lauryl acrylate) manufactured by NOF Corporation, 18 parts by mass of CLEARON M-105 (aromatic modified hydrogenated terpene resin) manufactured by Yashara Chemical Co., Ltd., LV- manufactured by JX Nippon Oil & Energy Corporation 10 parts by mass of 100 (polybutene), 20 parts by mass of GI-2000 (1,2-hydrogenated polybutadiene glycol) manufactured by Nippon Soda Co., Ltd., 4-HBA (4-hydroxybutyl acrylate) 3 manufactured by Osaka Organic Chemical Industry Co., Ltd. Part by mass, 0.5 part by mass of LAMBSON speed cure TPO (2,4,6-trimethylbenzoyldiphenylphosphine oxide), B ASF IRGACURE184 (1-hydroxycyclohexyl phenyl ketone) 0.5 part by mass was heated to 70 ° C. and mixed to obtain a photosensitive resin composition of the present invention. The viscosity of this photosensitive resin composition was 4600 mPa · s.
配合例3
合成例3のポリウレタン化合物(E−3)15質量部、合成例4のアクリル酸エステル化合物(F−1)5質量部、新中村化学(株)製S−1800A(イソステアリルアクリレート)19質量部、日油(株)製ブレンマーLA(ラウリルアクリレート)10質量部、ヤスハラケミカル(株)製クリアロンM−105(芳香族変性水添テルペン樹脂)18質量部、JX日鉱日石エネルギー(株)製LV−100(ポリブテン)10質量部、日本曹達(株)製GI−2000(1,2−水素化ポリブタジエングリコール)20質量部、大阪有機化学工業(株)製4−HBA(4−ヒドロキシブチルアクリレート)3質量部、LAMBSON社製スピードキュアTPO(2,4,6−トリメチルベンゾイルジフェニルフォスフィンオキサイド)0.5質量部、BASF社製IRGACURE184(1−ヒドロキシシクロヘキシルフェニルケトン)0.5質量部を70℃に加温、混合し、本発明の感光性樹脂組成物を得た。この感光性樹脂組成物の粘度は5000mPa・sであった。
Formulation Example 3
15 parts by mass of the polyurethane compound (E-3) of Synthesis Example 3, 5 parts by mass of the acrylic ester compound (F-1) of Synthesis Example 4, 19 parts by mass of S-1800A (isostearyl acrylate) manufactured by Shin-Nakamura Chemical Co., Ltd. , 10 parts by mass of Bremer LA (lauryl acrylate) manufactured by NOF Corporation, 18 parts by mass of CLEARON M-105 (aromatic modified hydrogenated terpene resin) manufactured by Yashara Chemical Co., Ltd., LV- manufactured by JX Nippon Oil & Energy Corporation 10 parts by mass of 100 (polybutene), 20 parts by mass of GI-2000 (1,2-hydrogenated polybutadiene glycol) manufactured by Nippon Soda Co., Ltd., 4-HBA (4-hydroxybutyl acrylate) 3 manufactured by Osaka Organic Chemical Industry Co., Ltd. Part by mass, 0.5 part by mass of LAMBSON speed cure TPO (2,4,6-trimethylbenzoyldiphenylphosphine oxide), B ASF IRGACURE184 (1-hydroxycyclohexyl phenyl ketone) 0.5 part by mass was heated to 70 ° C. and mixed to obtain a photosensitive resin composition of the present invention. The viscosity of this photosensitive resin composition was 5000 mPa · s.
配合例4
合成例2のポリウレタン化合物(E−2)15質量部、大阪有機化学工業(株)製SPBDA−S30(アクリル酸エステル化合物)5質量部、新中村化学(株)製S−1800A(イソステアリルアクリレート)19質量部、日油(株)製ブレンマーLA(ラウリルアクリレート)10質量部、ヤスハラケミカル(株)製クリアロンM−105(芳香族変性水添テルペン樹脂)18質量部、JX日鉱日石エネルギー(株)製LV−100(ポリブテン)10質量部、日本曹達(株)製GI−2000(1,2−水素化ポリブタジエングリコール)20質量部、大阪有機化学工業(株)製4−HBA(4−ヒドロキシブチルアクリレート)3質量部、LAMBSON社製スピードキュアTPO(2,4,6−トリメチルベンゾイルジフェニルフォスフィンオキサイド)0.5質量部、BASF社製IRGACURE184(1−ヒドロキシシクロヘキシルフェニルケトン)0.5質量部を70℃に加温、混合し、本発明の感光性樹脂組成物を得た。この感光性樹脂組成物の粘度は5500mPa・sであった。
Formulation Example 4
15 parts by mass of the polyurethane compound (E-2) of Synthesis Example 2, 5 parts by mass of SPBDA-S30 (acrylic ester compound) manufactured by Osaka Organic Chemical Industry Co., Ltd., S-1800A (isostearyl acrylate) manufactured by Shin-Nakamura Chemical Co., Ltd. ) 19 parts by mass, 10 parts by mass of Blenmer LA (lauryl acrylate) manufactured by NOF Corporation, 18 parts by mass of Clearon M-105 (aromatically modified hydrogenated terpene resin) manufactured by Yashara Chemicals, JX Nippon Oil & Energy Corporation ) LV-100 (polybutene) 10 parts by mass, Nippon Soda Co., Ltd. GI-2000 (1,2-hydrogenated polybutadiene glycol) 20 parts by mass, Osaka Organic Chemical Industry Co., Ltd. 4-HBA (4-hydroxy) Butyl acrylate) 3 parts by mass, LAMBSON speed cure TPO (2,4,6-trimethylbenzoyldiphenylphosphine) 0.5 parts by weight of oxide) and 0.5 parts by weight of IRGACURE184 (1-hydroxycyclohexyl phenyl ketone) manufactured by BASF were heated to 70 ° C. and mixed to obtain a photosensitive resin composition of the present invention. The viscosity of this photosensitive resin composition was 5500 mPa · s.
配合例1〜4を表1に示し、以下の評価を行った。
(粘度)E型粘度計(TV−200:東機産業(株)製)を用い、25℃にて測定した。 (Viscosity) It was measured at 25 ° C. using an E-type viscometer (TV-200: manufactured by Toki Sangyo Co., Ltd.).
(屈折率)樹脂の屈折率(25℃)をアッベ屈折率計(DR−M2:(株)アタゴ製)で測定した。 (Refractive index) The refractive index (25 ° C.) of the resin was measured with an Abbe refractometer (DR-M2: manufactured by Atago Co., Ltd.).
(硬化収縮率)フッ素系離型剤を塗布した厚さ1mmのスライドガラス2枚を用意し、そのうち1枚の離型剤塗布面に、得られた紫外線硬化型樹脂組成物を膜厚が200μmとなるよう塗布した。その後、2枚のスライドガラスを、それぞれの離型剤塗布面が互いに向かい合うように貼り合わせた。ガラス越しに高圧水銀灯(80W/cm、オゾンレス)で積算光量3000mJ/cm2の紫外線を該樹脂組成物に照射し、該樹脂組成物を硬化させた。その後、2枚のスライドガラスを剥離し、膜比重測定用の硬化物を作製した。JIS K7112 B法に準拠し、硬化物の比重(DS)を測定した。また、25℃で樹脂組成物の液比重(DL)を測定した。DS及びDLの測定結果から、次式より硬化収縮率を算出したところ、2.5%未満であった。
硬化収縮率(%)=(DS−DL)÷DS×100
(Curing shrinkage rate) Two 1 mm thick glass slides coated with a fluorine-based mold release agent were prepared, and the film thickness of the obtained ultraviolet curable resin composition was 200 μm on one mold release agent application surface. It applied so that it might become. Thereafter, the two slide glasses were bonded so that the respective release agent application surfaces face each other. The resin composition was cured by irradiating the resin composition with ultraviolet rays having an integrated light quantity of 3000 mJ / cm 2 through a glass with a high-pressure mercury lamp (80 W / cm, ozone-less). Thereafter, the two slide glasses were peeled off to produce a cured product for measuring the film specific gravity. Based on JIS K7112 B method, specific gravity (DS) of hardened | cured material was measured. Moreover, the liquid specific gravity (DL) of the resin composition was measured at 25 degreeC. From the measurement results of DS and DL, the cure shrinkage rate was calculated from the following formula and found to be less than 2.5%.
Curing shrinkage (%) = (DS−DL) ÷ DS × 100
(剛性率)離型処理されたPETフィルムを2枚用意し、そのうち1枚の離形面に、得られた紫外線硬化型樹脂組成物を膜厚が200μmとなるように塗布した。その後、2枚のPETフィルムを、それぞれ離型面が互いに向かい合うように貼り合せた。PETフィルム越しに高圧水銀灯(80W/cm、オゾンレス)で積算光量3000mJ/cm2の紫外線を該樹脂組成物に照射し、該樹脂組成物を硬化させた。その後、2枚のPETフィルムを剥離し、剛性率測定用の硬化物を作製した。剛性率はARES(TA Instruments社製)で測定した。 (Rigidity) Two PET films subjected to a release treatment were prepared, and the obtained ultraviolet curable resin composition was applied to one of the release surfaces so that the film thickness was 200 μm. Thereafter, the two PET films were bonded together such that the release surfaces face each other. The resin composition was cured by irradiating the resin composition with ultraviolet rays having an integrated light quantity of 3000 mJ / cm 2 through a PET film with a high-pressure mercury lamp (80 W / cm, ozone-less). Thereafter, the two PET films were peeled off to prepare a cured product for measuring the rigidity. The rigidity was measured with ARES (manufactured by TA Instruments).
(透過率)厚さ1mmのスライドガラス2枚を用意し、そのうちの1枚に、得られた紫外線硬化型樹脂組成物を硬化後の膜厚が200μmとなるように塗布した。その後、2枚のスライドガラスを貼り合わせた。ガラス越しに高圧水銀灯(80W/cm、オゾンレス)で積算光量3000mJ/cm2の紫外線照射し、該樹脂組成物を硬化させ、透過率測定用の硬化物を作製した。得られた硬化物の透明性については、分光光度計(U−3310、日立ハイテクノロジーズ(株))を用いて、400〜800nm及び400〜450nmの波長領域における透過率を測定した。その結果、400〜800nmの透過率90%以上であり、かつ、400〜450nmの透過率が90%以上であった。 (Transmittance) Two slide glasses having a thickness of 1 mm were prepared, and the obtained ultraviolet curable resin composition was applied to one of them so that the film thickness after curing was 200 μm. Then, two slide glasses were bonded together. The resin composition was cured by irradiating ultraviolet rays with an integrated light amount of 3000 mJ / cm 2 with a high-pressure mercury lamp (80 W / cm, ozone-less) through the glass to prepare a cured product for measuring transmittance. About the transparency of the obtained hardened | cured material, the transmittance | permeability in the wavelength range of 400-800 nm and 400-450 nm was measured using the spectrophotometer (U-3310, Hitachi High-Technologies Corporation). As a result, the transmittance of 400 to 800 nm was 90% or more, and the transmittance of 400 to 450 nm was 90% or more.
(耐熱、耐湿接着性)厚さ1mmのスライドガラスと厚さ1mmのガラス板、若しくは片面に偏光フィルムを貼った厚さ1mmのガラス板を用意し、一方に得られた紫外線硬化型樹脂組成物を膜厚が200μmとなるように塗布した後、その塗布面に他方を貼り合わせた。ガラス越しに、高圧水銀灯(80W/cm、オゾンレス)で積算光量3000mJ/cm2の紫外線を該樹脂組成物に照射し、該樹脂組成物を硬化させ、接着性評価用サンプルを作製した。これを用いて、85℃の耐熱試験、60℃90%RHの耐湿試験を行い、100時間放置した。その評価用サンプルにおいて、目視にてガラス又は偏光フィルムからの樹脂硬化物の剥がれを確認したが、剥がれはなかった。 (Heat and moisture resistant adhesion) A 1 mm thick glass slide and a 1 mm thick glass plate, or a 1 mm thick glass plate with a polarizing film pasted on one side, and an ultraviolet curable resin composition obtained on one side Was applied so that the film thickness was 200 μm, and the other was bonded to the coated surface. Through the glass, the resin composition was irradiated with ultraviolet rays having an integrated light amount of 3000 mJ / cm 2 with a high-pressure mercury lamp (80 W / cm, ozone-less), and the resin composition was cured to prepare a sample for evaluating adhesiveness. Using this, a heat resistance test at 85 ° C. and a humidity resistance test at 60 ° C. and 90% RH were conducted and left for 100 hours. In the sample for evaluation, peeling of the cured resin from the glass or polarizing film was confirmed visually, but there was no peeling.
本発明のポリウレタン化合物および(メタ)アクリル酸エステル化合物を含有する感光性樹脂組成物は柔軟性に優れ、耐候性、耐光性が高く、透明性に優れているため光学用途部材としてとして有用である。更に本発明の感光性樹脂組成物の硬化物は透明な表示体基板を貼り合せる接着剤として有用である。
The photosensitive resin composition containing the polyurethane compound and the (meth) acrylic acid ester compound of the present invention is excellent in flexibility, weather resistance, light resistance, and transparency, and thus is useful as an optical use member. . Furthermore, the cured product of the photosensitive resin composition of the present invention is useful as an adhesive for bonding a transparent display substrate.
Claims (9)
化合物(A):水添ポリブタジエンポリオール化合物
化合物(B):ポリイソシアネート化合物
化合物(C):少なくとも1つ以上の水酸基を有する(メタ)アクリレート化合物
化合物(D):化合物(A)以外のジオール化合物 The polyurethane resin (E) obtained by reacting the compound (C) with the compound (A), the compound (B), and the compound (D) shown below , and the (meth) acrylic compound (A). A resin composition (G) comprising an acid ester compound (F).
Compound (A): Hydrogenated polybutadiene polyol compound Compound (B): Polyisocyanate compound Compound (C): (Meth) acrylate compound having at least one hydroxyl group Compound (D): Diol compound other than Compound (A)
Hardened | cured material of the resin composition as described in any one of Claims 1 thru | or 8.
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CN201580049354.8A CN106715500A (en) | 2014-09-12 | 2015-09-08 | Resin composition, polymerizable resin composition, photosensitive resin composition, and cured products of said resin compositions |
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JP2017057349A (en) * | 2015-09-18 | 2017-03-23 | 日本化薬株式会社 | Polyurethane compound and resin composition containing the same |
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