JP4255392B2 - (Meth) acrylic acid and / or esters thereof, photocurable composition containing the same, and cured product thereof - Google Patents
(Meth) acrylic acid and / or esters thereof, photocurable composition containing the same, and cured product thereof Download PDFInfo
- Publication number
- JP4255392B2 JP4255392B2 JP2004069627A JP2004069627A JP4255392B2 JP 4255392 B2 JP4255392 B2 JP 4255392B2 JP 2004069627 A JP2004069627 A JP 2004069627A JP 2004069627 A JP2004069627 A JP 2004069627A JP 4255392 B2 JP4255392 B2 JP 4255392B2
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acrylate
- acrylic acid
- group
- acid esters
- 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.)
- Expired - Lifetime
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 50
- 239000000203 mixture Substances 0.000 title claims description 26
- 150000002148 esters Chemical class 0.000 title description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 102
- 239000003963 antioxidant agent Substances 0.000 claims description 25
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 21
- 230000003078 antioxidant effect Effects 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 16
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000000016 photochemical curing Methods 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000001723 curing Methods 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical group CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 5
- 229920000193 polymethacrylate Polymers 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 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 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 2
- -1 oxypropylene group Chemical group 0.000 description 63
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 9
- 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 8
- 238000003860 storage Methods 0.000 description 8
- 239000003822 epoxy resin Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000011342 resin composition Substances 0.000 description 5
- 229960000834 vinyl ether Drugs 0.000 description 5
- 238000004383 yellowing Methods 0.000 description 5
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- CZNRFEXEPBITDS-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O CZNRFEXEPBITDS-UHFFFAOYSA-N 0.000 description 3
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 3
- BGRKGHSKCFAPCL-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=CC=C1O BGRKGHSKCFAPCL-UHFFFAOYSA-N 0.000 description 3
- VMPHCHVAKMAZAN-UHFFFAOYSA-N 2-tert-butyl-4-(isocyanatomethyl)phenol Chemical compound C(C)(C)(C)C=1C=C(CN=C=O)C=CC1O VMPHCHVAKMAZAN-UHFFFAOYSA-N 0.000 description 3
- HXUFDTZKAGCOKY-UHFFFAOYSA-N 4-[[3,5-bis[(3-tert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2-tert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=CC=2)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=CC=2)C(C)(C)C)C(C)=C1CC1=CC=C(O)C(C(C)(C)C)=C1 HXUFDTZKAGCOKY-UHFFFAOYSA-N 0.000 description 3
- GXCIIGDHBSMEEA-UHFFFAOYSA-N 5-methyl-2-(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=C(C)C=C1O GXCIIGDHBSMEEA-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000004843 novolac epoxy resin Substances 0.000 description 3
- 239000002530 phenolic antioxidant Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 2
- AKFDJVNJIKKISD-UHFFFAOYSA-N 1,1-bis(2-tert-butyl-4-hydroxyphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C=CC(=C1)O)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)O)C(C)(C)C AKFDJVNJIKKISD-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 2
- QVOHHWQAOFEPOQ-UHFFFAOYSA-N 1,3-bis(ethenoxy)butane Chemical compound C=COC(C)CCOC=C QVOHHWQAOFEPOQ-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- FKWOGPPGVRDIRZ-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=CC=C1O FKWOGPPGVRDIRZ-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- BTVWZWFKMIUSGS-UHFFFAOYSA-N 2-methylpropane-1,2-diol Chemical compound CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
- WXCNGLBCODDPGQ-UHFFFAOYSA-N 3-(3-tert-butyl-4-hydroxyphenyl)-n-[6-[3-(3-tert-butyl-4-hydroxyphenyl)propanoylamino]hexyl]propanamide Chemical compound C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NCCCCCCNC(=O)CCC=2C=C(C(O)=CC=2)C(C)(C)C)=C1 WXCNGLBCODDPGQ-UHFFFAOYSA-N 0.000 description 2
- COMNHTLIGAOZMU-UHFFFAOYSA-N 4-[4,4-bis[2-ethyl-4-hydroxy-5-(2-methylbutan-2-yl)phenyl]butan-2-yl]-5-ethyl-2-(2-methylbutan-2-yl)phenol Chemical compound CCC1=CC(O)=C(C(C)(C)CC)C=C1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)CC)CC)C1=CC(C(C)(C)CC)=C(O)C=C1CC COMNHTLIGAOZMU-UHFFFAOYSA-N 0.000 description 2
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NANGRQNYIZPFAZ-UHFFFAOYSA-N C(C)(C)(CC)C=1C=C(CN=C=O)C=CC1O Chemical compound C(C)(C)(CC)C=1C=C(CN=C=O)C=CC1O NANGRQNYIZPFAZ-UHFFFAOYSA-N 0.000 description 2
- CZBPGKWNVUOKFB-UHFFFAOYSA-N C.C=C(C(=O)O)CC1=CC(=C(C=C1)O)C(C)(C)C.C=C(C(=O)O)CC1=CC(=C(C=C1)O)C(C)(C)C.C=C(C(=O)O)CC1=CC(=C(C=C1)O)C(C)(C)C.C=C(C(=O)O)CC1=CC(=C(C=C1)O)C(C)(C)C Chemical compound C.C=C(C(=O)O)CC1=CC(=C(C=C1)O)C(C)(C)C.C=C(C(=O)O)CC1=CC(=C(C=C1)O)C(C)(C)C.C=C(C(=O)O)CC1=CC(=C(C=C1)O)C(C)(C)C.C=C(C(=O)O)CC1=CC(=C(C=C1)O)C(C)(C)C CZBPGKWNVUOKFB-UHFFFAOYSA-N 0.000 description 2
- LYPJKORWSCCJIB-UHFFFAOYSA-N CC1=CC=CC=C1CC(C)(I)C1=CC=CC=C1 Chemical compound CC1=CC=CC=C1CC(C)(I)C1=CC=CC=C1 LYPJKORWSCCJIB-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000005410 aryl sulfonium group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 150000007519 polyprotic acids Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
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- 229940005650 monomethyl fumarate Drugs 0.000 description 1
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- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
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- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
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- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
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- 150000003077 polyols Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical group C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 239000012748 slip agent Substances 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 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
- 239000013008 thixotropic agent Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- XEUQZCPDHUIJIR-UHFFFAOYSA-N tris[4-hydroxy-2-(2-methylbutan-2-yl)phenyl] phosphite Chemical compound P(OC1=C(C=C(C=C1)O)C(C)(C)CC)(OC1=C(C=C(C=C1)O)C(C)(C)CC)OC1=C(C=C(C=C1)O)C(C)(C)CC XEUQZCPDHUIJIR-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- INRGAWUQFOBNKL-UHFFFAOYSA-N {4-[(Vinyloxy)methyl]cyclohexyl}methanol Chemical compound OCC1CCC(COC=C)CC1 INRGAWUQFOBNKL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、(メタ)アクリル酸及び/又はそのエステル類、それを含む光硬化用組成物並びにその硬化物に関する。より詳しくは、酸化防止剤を含む(メタ)アクリル酸及び/又はそのエステル類、それを含む光硬化用組成物並びにその硬化物に関する。 The present invention relates to (meth) acrylic acid and / or esters thereof, a photocurable composition containing the same, and a cured product thereof. More specifically, the present invention relates to (meth) acrylic acid and / or esters thereof containing an antioxidant, a photocurable composition containing the same, and a cured product thereof.
(メタ)アクリル酸やそのエステル類は、重合性単量体であることから、様々な工業製品の原料等として各種用途に用いられる化合物であり、保存安定性の点から酸化防止剤を含有するものが知られている。このような酸化防止剤を含有する(メタ)アクリル酸やそのエステル類は、特に光硬化に用いられる組成物を構成するものとして有用であることから、保存安定性だけでなく、光硬化性において向上したものが望まれている。 Since (meth) acrylic acid and its esters are polymerizable monomers, they are compounds used in various applications as raw materials for various industrial products and contain antioxidants from the viewpoint of storage stability. Things are known. (Meth) acrylic acid and its esters containing such an antioxidant are particularly useful as constituents of compositions used for photocuring, so that not only storage stability but also photocurability Improvements are desired.
このような酸化防止剤を含有する(メタ)アクリル酸やそのエステル類に関して、オキシプロピレン基を有する重合性オリゴマー、フェノール系酸化防止剤及び紫外線吸収剤を含有する液状硬化性樹脂組成物が開示されている(例えば、特許文献1参照。)。
この樹脂組成物は、耐光性を有し、例えば光ファイバ用被覆材料として用いられることが記載され、重合性オリゴマーとしては、オキシプロピレン基と(メタ)アクリル基とを有するものが例示されている。
A liquid curable resin composition containing a polymerizable oligomer having an oxypropylene group, a phenolic antioxidant and an ultraviolet absorber is disclosed for (meth) acrylic acid and esters thereof containing such an antioxidant. (For example, refer to Patent Document 1).
This resin composition has light resistance and is described as being used, for example, as a coating material for optical fibers. Examples of the polymerizable oligomer include those having an oxypropylene group and a (meth) acryl group. .
また基材上に複数の光硬化性樹脂硬化膜が積層されてなる多層被覆に関して、少なくとも隣接する2つの層には、同一のヒンダードフェノール系酸化防止剤を含有することが開示されている(例えば、特許文献2及び3参照。)。このような多層被覆を形成する樹脂組成物においては、熱的安定性及び蛍光灯下での色安定性の点からヒンダードフェノール系酸化防止剤が配合されることが記載され、また、ウレタン(メタ)アクリレートを含有することが好ましいことが記載されている。
しかしながら、これらの樹脂組成物においては、各種の用途において好適な状態で使用することができるように、樹脂組成物の保存安定性に優れるだけでなく、更に硬化物の黄変が低減され、かつ組成物の光硬化性においても充分に向上されたものとする工夫の余地があった。
However, in these resin compositions, not only is the storage stability of the resin composition excellent so that it can be used in various conditions, but further yellowing of the cured product is reduced, and There was room for improvement that the photocurability of the composition was sufficiently improved.
本発明は、上記現状に鑑みてなされたものであり、保存安定性を維持したまま、光硬化性が向上され、しかも硬化物が黄変を起こさない(メタ)アクリル酸及び/又はそのエステル類、それを含む光硬化用組成物並びにその硬化物を提供することを目的とするものである。 The present invention has been made in view of the above situation, and (meth) acrylic acid and / or esters thereof in which photocurability is improved and the cured product does not cause yellowing while maintaining storage stability. An object of the present invention is to provide a photocurable composition containing the same and a cured product thereof.
本発明者等は、光硬化に用いられる各種用途に有用な組成物について種々検討したところ、特定構造の酸化防止剤を、(メタ)アクリル酸及び/又はそのエステル類に用いることにより、保存安定性を維持したまま、光硬化性が向上するものとできることを見いだし、光重合開始剤の使用量や光の照射量を抑えても、充分な光硬化性を発揮することができることを見いだした。また、光硬化により得られる硬化物が黄変を起こさないという予期せぬ効果を発揮することも見いだし、上記課題をみごとに解決することができることに想到した。
酸化防止剤としては、従来からヒンダードフェノール系酸化防止剤、ハイドロキノン、メトキノン等が広く使用されているが、このような酸化防止剤を用いると、保存安定性は向上するものの、組成物の光硬化性が低下する場合があるが、特定構造を有する酸化防止剤を(メタ)アクリル酸及び/又はそのエステル類の酸化防止剤として用いることにより、上記作用効果を充分に発揮でき、各種用途に有用なものとできることを見いだし、本発明に到達したものである。
The inventors of the present invention have studied various compositions useful for various uses used for photocuring. As a result of using an antioxidant having a specific structure in (meth) acrylic acid and / or its esters, the storage stability is improved. The present inventors have found that photocurability can be improved while maintaining the properties, and that even if the amount of photopolymerization initiator used and the amount of light irradiation are suppressed, sufficient photocurability can be exhibited. It was also found that a cured product obtained by photocuring exhibits an unexpected effect that yellowing does not occur, and the inventors have conceived that the above problems can be solved brilliantly.
As antioxidants, hindered phenolic antioxidants, hydroquinone, methoquinone, and the like have been widely used. However, when such an antioxidant is used, although the storage stability is improved, the light of the composition Although the curability may be reduced, by using an antioxidant having a specific structure as an antioxidant for (meth) acrylic acid and / or its esters, the above-mentioned effects can be sufficiently exerted for various uses. It has been found that it can be useful, and has reached the present invention.
すなわち本発明は、酸化防止剤を含んでなる(メタ)アクリル酸及び/又はそのエステル類であって、上記酸化防止剤は、少なくともフェノール性水酸基を持つフェニル基を有し、上記フェノール性水酸基が結合している炭素原子に隣接する炭素原子の一方に水素原子が結合し、他方にアルキル基が結合する構造を有するものである(メタ)アクリル酸及び/又はそのエステル類である。
以下に本発明を詳述する。
That is, the present invention is (meth) acrylic acid and / or esters thereof containing an antioxidant, wherein the antioxidant has at least a phenyl group having a phenolic hydroxyl group, and the phenolic hydroxyl group is It is (meth) acrylic acid and / or its esters having a structure in which a hydrogen atom is bonded to one of the carbon atoms adjacent to the bonded carbon atom and an alkyl group is bonded to the other.
The present invention is described in detail below.
本発明において酸化防止剤は、置換基として少なくともフェノール性水酸基が結合するフェニル基を有する化合物であり、フェノール性水酸基が結合している炭素原子の両隣の炭素原子において、一方の炭素原子に水素原子が結合し、他方の炭素原子にアルキル基が結合する構造を有する化合物である。このような化合物としては、酸化防止剤としての効果を発揮し得るものであればよく、フェニル基がその他の置換基を有することになってもよい。このような酸化防止剤としては、下記一般式(1); In the present invention, the antioxidant is a compound having a phenyl group to which at least a phenolic hydroxyl group is bonded as a substituent, and a carbon atom adjacent to the carbon atom to which the phenolic hydroxyl group is bonded is a hydrogen atom on one carbon atom. Is a compound having a structure in which an alkyl group is bonded to the other carbon atom. Such a compound is not particularly limited as long as it can exhibit an effect as an antioxidant, and the phenyl group may have other substituents. As such an antioxidant, the following general formula (1);
(式中、R1は、炭素数1〜10のアルキル基を表す。R2は、同一若しくは異なって、水素原子、OH基又は炭素数1〜10のアルキル基を表す。Zは、水素原子、OH基又は有機残基を表す。nは、1以上の整数である。)で表される化合物であることが好ましい。
上記R1において、炭素数1〜10のアルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、s−ブチル基、t−ブチル基、ペンチル基、t−アミル基、イソペンチル基、ネオペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基等が好適である。これらの中でも、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、s−ブチル基、t−ブチル基、t−アミル基が好ましい。より好ましくは、t−ブチル基、t−アミル基である。
上記R2における炭素数1〜10のアルキル基としては、R1における炭素数1〜10のアルキル基と同様である。
(In the formula, R 1 represents an alkyl group having 1 to 10 carbon atoms. R 2 is the same or different and represents a hydrogen atom, an OH group or an alkyl group having 1 to 10 carbon atoms. Z represents a hydrogen atom. Represents an OH group or an organic residue, and n is an integer of 1 or more.
In the above R 1 , the alkyl group having 1 to 10 carbon atoms includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, and t-amyl. A group, isopentyl group, neopentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group and the like are preferable. Among these, a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, and t-amyl group are preferable. More preferably, they are a t-butyl group and a t-amyl group.
The alkyl group having 1 to 10 carbon atoms in R 2 is the same as the alkyl group having 1 to 10 carbon atoms in R 1 .
上記Zにおいて、有機残基としては、炭素数1〜40の有機残基が好適であり、例えば、直鎖状、分枝状又は環状のアルキル基;エーテル結合、エステル結合、アセタール結合、アミド結合、リン酸エステル結合、亜リン酸エステル結合の少なくとも1つを有する有機残基;置換されていてもよい芳香族基等が好適である。これらの中でも、直鎖状又は分枝状の炭素数2〜6のアルキル基、エステル結合を有する炭素数10〜30の有機残基、エーテル結合及びエステル結合を有する炭素数10〜30の有機残基、アミド結合を有する炭素数6〜15の有機残基、エステル結合及びアミド結合を有する炭素数10〜30の有機残基、エステル結合及びアセタール結合を有する炭素数20〜40の有機残基、炭素数6〜10の芳香族基等が好ましい。より好ましくは、ブタン骨格残基、ペンタン骨格残基である。
上記nは、1以上の整数であり、1〜5が好適である。好ましくは、1〜3である。
In Z above, the organic residue is preferably an organic residue having 1 to 40 carbon atoms, such as a linear, branched or cyclic alkyl group; an ether bond, an ester bond, an acetal bond, an amide bond. An organic residue having at least one of a phosphate ester bond and a phosphite ester bond; an optionally substituted aromatic group, and the like are preferable. Among these, linear or branched alkyl groups having 2 to 6 carbon atoms, organic residues having 10 to 30 carbon atoms having ester bonds, organic residues having 10 to 30 carbon atoms having ether bonds and ester bonds. Group, an organic residue having 6 to 15 carbon atoms having an amide bond, an organic residue having 10 to 30 carbon atoms having an ester bond and an amide bond, an organic residue having 20 to 40 carbon atoms having an ester bond and an acetal bond, An aromatic group having 6 to 10 carbon atoms is preferred. More preferred are a butane skeleton residue and a pentane skeleton residue.
Said n is an integer greater than or equal to 1, and 1-5 are suitable. Preferably, it is 1-3.
上記酸化防止剤としては、例えば、下記のような化合物等が好適である。これらは1種又は2種以上を用いることができる。
2−t−ブチルフェノール、2−t−アミルフェノール、2−t−ブチルハイドロキノン、2−t−アミルハイドロキノン、2−t−ブチル−4−メトキシハイドロキノン、2−t−アミル−4−メトキシハイドロキノン、2,3−ジ−t−ブチルフェノール、2,3−ジ−t−アミルフェノール、2,3−ジ−t−ブチルハイドロキノン、2,3−ジ−t−アミルハイドロキノン、2,3−ジ−t−ブチル−4−メトキシハイドロキノン、2,3−ジ−t−アミル−4−メトキシハイドロキノン、2,5−ジ−t−ブチルフェノール、2,5−ジ−t−アミルフェノール、2,5−ジ−t−ブチルハイドロキノン、2,5−ジ−t−アミルハイドロキノン、2,5−ジ−t−ブチル−4−メトキシハイドロキノン、2,5−ジ−t−アミル−4−メトキシハイドロキノン、トリス(3−t−ブチル−4−ヒドロキシベンジル)イソシアネート、トリス(3−t−アミル−4−ヒドロキシベンジル)イソシアネート、
As said antioxidant, the following compounds etc. are suitable, for example. These can use 1 type (s) or 2 or more types.
2-t-butylphenol, 2-t-amylphenol, 2-t-butylhydroquinone, 2-t-amylhydroquinone, 2-t-butyl-4-methoxyhydroquinone, 2-t-amyl-4-methoxyhydroquinone, 2 , 3-di-t-butylphenol, 2,3-di-t-amylphenol, 2,3-di-t-butylhydroquinone, 2,3-di-t-amylhydroquinone, 2,3-di-t- Butyl-4-methoxyhydroquinone, 2,3-di-t-amyl-4-methoxyhydroquinone, 2,5-di-t-butylphenol, 2,5-di-t-amylphenol, 2,5-di-t -Butylhydroquinone, 2,5-di-t-amylhydroquinone, 2,5-di-t-butyl-4-methoxyhydroquinone, 2,5-di-t-amyl 4-methoxy hydroquinone, tris (3-t-butyl-4-hydroxybenzyl) isocyanate, tris (3-t-amyl-4-hydroxybenzyl) isocyanate,
1,1,3−トリス(2−メチル−4−ヒドロキシ−5−t−ブチルフェニル)ブタン、1,1,3−トリス(4−ヒドロキシ−5−t−ブチルフェニル)ブタン、1,1,3−トリス(2−エチル−4−ヒドロキシ−5−t−ブチルフェニル)ブタン、1,1,3−トリス(2−プロピル−4−ヒドロキシ−5−t−ブチルフェニル)ブタン、1,1,3−トリス(2,5−ジ−t−ブチル−4−ヒドロキシフェニル)ブタン、1,1,3−トリス(2,6−ジメチル−4−ヒドロキシ−5−t−ブチルフェニル)ブタン、1,1,3−トリス(2,5,6−トリ−t−ブチル−4−ヒドロキシフェニル)ブタン、1,1,3−トリス(2−メチル−4−ヒドロキシ−5−t−アミルフェニル)ブタン、1,1,3−トリス(4−ヒドロキシ−5−t−アミルフェニル)ブタン、1,1,3−トリス(2−エチル−4−ヒドロキシ−5−t−アミルフェニル)ブタン、1,1,3−トリス(2−プロピル−4−ヒドロキシ−5−t−アミルフェニル)ブタン、1,1,3−トリス(2,5−ジ−t−アミル−4−ヒドロキシフェニル)ブタン、1,1,3−トリス(2,6−ジメチル−4−ヒドロキシ−5−t−アミルフェニル)ブタン、1,1,3−トリス(2,5,6−トリ−t−アミル−4−ヒドロキシフェニル)ブタン、 1,1,3-tris (2-methyl-4-hydroxy-5-t-butylphenyl) butane, 1,1,3-tris (4-hydroxy-5-t-butylphenyl) butane, 1,1, 3-tris (2-ethyl-4-hydroxy-5-t-butylphenyl) butane, 1,1,3-tris (2-propyl-4-hydroxy-5-t-butylphenyl) butane, 1,1, 3-tris (2,5-di-t-butyl-4-hydroxyphenyl) butane, 1,1,3-tris (2,6-dimethyl-4-hydroxy-5-tert-butylphenyl) butane, 1, 1,3-tris (2,5,6-tri-t-butyl-4-hydroxyphenyl) butane, 1,1,3-tris (2-methyl-4-hydroxy-5-t-amylphenyl) butane, 1,1,3-tris (4-hydroxy -5-t-amylphenyl) butane, 1,1,3-tris (2-ethyl-4-hydroxy-5-t-amylphenyl) butane, 1,1,3-tris (2-propyl-4-hydroxy) -5-t-amylphenyl) butane, 1,1,3-tris (2,5-di-t-amyl-4-hydroxyphenyl) butane, 1,1,3-tris (2,6-dimethyl-4) -Hydroxy-5-t-amylphenyl) butane, 1,1,3-tris (2,5,6-tri-t-amyl-4-hydroxyphenyl) butane,
4,4−ブチリデン−ビス(6−t−ブチルフェノール)、4,4−ブチリデン−ビス(3−メチル−6−t−ブチルフェノール)、4,4−ブチリデン−ビス(3,5−ジメチル−6−t−ブチルフェノール)、4,4−ブチリデン−ビス(3,5,6−トリ−t−ブチルフェノール)、4,4−ブチリデン−ビス(6−t−アミルフェノール)、4,4−ブチリデン−ビス(3−メチル−6−t−アミルフェノール)、4,4−ブチリデン−ビス(3,5−ジメチル−6−t−アミルフェノール)、4,4−ブチリデン−ビス(3,5,6−トリ−t−アミルフェノール)、3−(3−t−ブチル−4−ヒドロキシフェニル)プロピオン酸へキサデシル、3−(3−t−ブチル−4−ヒドロキシフェニル)プロピオン酸オクタデシル、3−(3−t−アミル−4−ヒドロキシフェニル)プロピオン酸ヘキサデシル、3−(3−t−アミル−4−ヒドロキシフェニル)プロピオン酸オクタデシル、テトラキス[メチレン−3−(3−t−ブチル−4−ヒドロキシフェニル)プロピオネート]メタン、テトラキス[メチレン−3−(3−t−アミル−4−ヒドロキシフェニル)プロピオネート]メタン、トリエチレングリコールビス[3−(3−t−ブチル−4−ヒドロキシフェニル)プロピオネート]、トリエチレングリコールビス[3−(3−t−アミル−4−ヒドロキシフェニル)プロピオネート]、 4,4-butylidene-bis (6-tert-butylphenol), 4,4-butylidene-bis (3-methyl-6-tert-butylphenol), 4,4-butylidene-bis (3,5-dimethyl-6- t-butylphenol), 4,4-butylidene-bis (3,5,6-tri-tert-butylphenol), 4,4-butylidene-bis (6-t-amylphenol), 4,4-butylidene-bis ( 3-methyl-6-t-amylphenol), 4,4-butylidene-bis (3,5-dimethyl-6-t-amylphenol), 4,4-butylidene-bis (3,5,6-tri-) t-amylphenol), hexadecyl 3- (3-t-butyl-4-hydroxyphenyl) propionate, octadecyl 3- (3-t-butyl-4-hydroxyphenyl) propionate, 3 Hexadecyl (3-t-amyl-4-hydroxyphenyl) propionate, octadecyl 3- (3-t-amyl-4-hydroxyphenyl) propionate, tetrakis [methylene-3- (3-t-butyl-4-hydroxy Phenyl) propionate] methane, tetrakis [methylene-3- (3-t-amyl-4-hydroxyphenyl) propionate] methane, triethylene glycol bis [3- (3-t-butyl-4-hydroxyphenyl) propionate], Triethylene glycol bis [3- (3-t-amyl-4-hydroxyphenyl) propionate],
3,9−ビス[1,1−ジ−メチル−2−{β−(3−t−ブチル−4−ヒドロキシフェニル)プロピノニルオキシ}エチル]−2,4,8,10−テトラオキサスピロ[5,5]ウンデカン、3,9−ビス[1,1−ジ−メチル−2−{β−(3−t−アミル−4−ヒドロキシフェニル)プロピノニルオキシ}エチル]−2,4,8,10−テトラオキサスピロ[5,5]ウンデカン、1,3,5−トリメチル−2,4,6−トリス(3−t−ブチル−4−ヒドロキシベンジル)ベンゼン、1,3,5−トリメチル−2,4,6−トリス(3−t−アミル−4−ヒドロキシベンジル)ベンゼン、N,N′−ビス[3−(3−t−ブチル−4−ヒドロキシフェニル)プロピオニル]へキサメチレンジアミン、3−t−ブチル−4−ヒドロキシベンジルホスフェートジエチルエステル、3−t−アミル−4−ヒドロキシベンジルホスフェートジエチルエステル、ジ(2−t−ブチル−4−ヒドロキシフェニル)ペンタエリスリトールジホスファイト、ジ(2−t−アミル−4−ヒドロキシフェニル)ペンタエリスリトールジホスファイト、トリス(2−t−ブチル−4−ヒドロキシフェニル)ホスファイト、トリス(2−t−アミル−4−ヒドロキシフェニル)ホスファイト、2,2′−オキサミドビス[エチル−3−(3−t−ブチル−4−ヒドロキシフェニル)プロピオネート]、2,2′−オキサミドビス[エチル−3−(3−t−ブチル−4−ヒドロキシフェニル)プロピオネート]。 3,9-bis [1,1-di-methyl-2- {β- (3-tert-butyl-4-hydroxyphenyl) propynyloxy} ethyl] -2,4,8,10-tetraoxaspiro [ 5,5] undecane, 3,9-bis [1,1-di-methyl-2- {β- (3-t-amyl-4-hydroxyphenyl) propinonyloxy} ethyl] -2,4,8, 10-tetraoxaspiro [5,5] undecane, 1,3,5-trimethyl-2,4,6-tris (3-tert-butyl-4-hydroxybenzyl) benzene, 1,3,5-trimethyl-2 , 4,6-tris (3-t-amyl-4-hydroxybenzyl) benzene, N, N′-bis [3- (3-t-butyl-4-hydroxyphenyl) propionyl] hexamethylenediamine, 3- t-Butyl-4-hydroxybe Benzyl phosphate diethyl ester, 3-tert-amyl-4-hydroxybenzyl phosphate diethyl ester, di (2-tert-butyl-4-hydroxyphenyl) pentaerythritol diphosphite, di (2-tert-amyl-4-hydroxy) Phenyl) pentaerythritol diphosphite, tris (2-tert-butyl-4-hydroxyphenyl) phosphite, tris (2-tert-amyl-4-hydroxyphenyl) phosphite, 2,2′-oxamidobis [ethyl-3 -(3-t-butyl-4-hydroxyphenyl) propionate], 2,2'-oxamidobis [ethyl-3- (3-t-butyl-4-hydroxyphenyl) propionate].
これらの中でも、2−t−ブチルハイドロキノン、2−t−アミルハイドロキノン、2,5−ジ−t−ブチルハイドロキノン、2,5−ジ−t−アミルハイドロキノン、トリス(3−t−ブチル−4−ヒドロキシベンジル)イソシアネート、トリス(3−t−アミル−4−ヒドロキシベンジル)イソシアネート、1,1,3−トリス(2−メチル−4−ヒドロキシ−5−t−ブチルフェニル)ブタン、1,1,3−トリス(2−エチル−4−ヒドロキシ−5−t−アミルフェニル)ブタン、4.4−ブチリデン−ビス(3−メチル−6−t−ブチルフェノール)、4,4−ブチリデン−ビス(3−メチル−6−t−アミルフェノール)、テトラキス[メチレン−3−(3−t−ブチル−4−ヒドロキシフェニル)プロピオネート]メタン、トリエチレングリコールビス[3−(3−t−ブチル−4−ヒドロキシフェニル)プロピオネート]、3,9−ビス[1,1−ジ−メチル−2−{β−(3−t−ブチル−4−ヒドロキシフェニル)プロピノニルオキシ}エチル]−2,4,8,10−テトラオキサスピロ[5,5]ウンデカン、1,3,5−トリメチル−2,4,6−トリス(3−t−ブチル−4−ヒドロキシベンジル)ベンゼン、N,N′−ビス[3−(3−t−ブチル−4−ヒドロキシフェニル)プロピオニル]ヘキサメチレンジアミン、3−t−ブチル−4−ヒドロキシベンジルホスフェートジエチルエステル、ジ(2−t−ブチル−4−ヒドロキシフェニル)ペンタエリスリトールジホスファイト、トリス(2−t−ブチル−4−ヒドロキシフェニル)ホスファイト、2,2′−オキサミドビス[エチル−3−(3−t−ブチル−4−ヒドロキシフェニル)プロピオネート]等が好ましい。 Among these, 2-t-butylhydroquinone, 2-t-amylhydroquinone, 2,5-di-t-butylhydroquinone, 2,5-di-t-amylhydroquinone, tris (3-t-butyl-4- Hydroxybenzyl) isocyanate, tris (3-t-amyl-4-hydroxybenzyl) isocyanate, 1,1,3-tris (2-methyl-4-hydroxy-5-t-butylphenyl) butane, 1,1,3 -Tris (2-ethyl-4-hydroxy-5-t-amylphenyl) butane, 4.4-butylidene-bis (3-methyl-6-t-butylphenol), 4,4-butylidene-bis (3-methyl -6-t-amylphenol), tetrakis [methylene-3- (3-tert-butyl-4-hydroxyphenyl) propionate] methane, Ethylene glycol bis [3- (3-t-butyl-4-hydroxyphenyl) propionate], 3,9-bis [1,1-di-methyl-2- {β- (3-t-butyl-4-hydroxy) Phenyl) propynonyloxy} ethyl] -2,4,8,10-tetraoxaspiro [5,5] undecane, 1,3,5-trimethyl-2,4,6-tris (3-t-butyl-4 -Hydroxybenzyl) benzene, N, N'-bis [3- (3-tert-butyl-4-hydroxyphenyl) propionyl] hexamethylenediamine, 3-tert-butyl-4-hydroxybenzyl phosphate diethyl ester, di (2 -T-butyl-4-hydroxyphenyl) pentaerythritol diphosphite, tris (2-t-butyl-4-hydroxyphenyl) phosphite, 2,2′-oxamidobis [ethyl-3- (3-tert-butyl-4-hydroxyphenyl) propionate] and the like are preferable.
より好ましくは、2,5−ジ−t−ブチルハイドロキノン、2,5−ジ−t−アミルハイドロキノン、トリス(3−t−ブチル−4−ヒドロキシベンジル)イソシアネート、トリス(3−t−アミル−4−ヒドロキシベンジル)イソシアネ−ト、1,1,3−トリス(2−メチル−4−ヒドロキシ−5−t−ブチルフェニル)ブタン、1,1,3−トリス(2−エチル−4−ヒドロキシ−5−t−アミルフェニル)ブタン、4,4−ブチリデン−ビス(3−メチル−6−t−ブチルフェノール)、4,4−ブチリデン−ビス(3−メチル−6−t−アミルフェノール)、1,3,5−トリメチル−2,4,6−トリス(3−t−ブチル−4−ヒドロキシベンジル)ベンゼン等である。 More preferably, 2,5-di-t-butylhydroquinone, 2,5-di-t-amylhydroquinone, tris (3-t-butyl-4-hydroxybenzyl) isocyanate, tris (3-t-amyl-4) -Hydroxybenzyl) isocyanate, 1,1,3-tris (2-methyl-4-hydroxy-5-t-butylphenyl) butane, 1,1,3-tris (2-ethyl-4-hydroxy-5) -T-amylphenyl) butane, 4,4-butylidene-bis (3-methyl-6-t-butylphenol), 4,4-butylidene-bis (3-methyl-6-t-amylphenol), 1,3 , 5-trimethyl-2,4,6-tris (3-t-butyl-4-hydroxybenzyl) benzene.
上記酸化防止剤の使用量としては、酸化防止剤を含まない(メタ)アクリル酸及び/又はエステル類に対して、下限値としては1質量ppmであることが好ましい。1質量ppm未満であると、保存安定性を充分には向上できないおそれがある。より好ましくは、5質量ppmであり、更に好ましくは、10質量ppmであり、更に好ましくは、20質量ppmであり、特に好ましくは、50質量ppmであり、最も好ましくは、100質量ppmである。上限値としては、10000質量ppmであることが好ましい。10000質量ppmを超えると、光硬化性が充分には向上しないおそれがある。より好ましくは、5000質量ppmであり、更に好ましくは、2000質量ppmであり、特に好ましくは、1000質量ppmである。また、好ましい範囲としては、20〜2000質量ppmであり、より好ましくは、50〜1000質量ppmである。 As the usage-amount of the said antioxidant, it is preferable that it is 1 mass ppm as a lower limit with respect to (meth) acrylic acid and / or esters which do not contain antioxidant. If it is less than 1 ppm by mass, the storage stability may not be sufficiently improved. More preferably, it is 5 mass ppm, More preferably, it is 10 mass ppm, More preferably, it is 20 mass ppm, Especially preferably, it is 50 mass ppm, Most preferably, it is 100 mass ppm. The upper limit is preferably 10,000 ppm by mass. If it exceeds 10,000 mass ppm, the photocurability may not be sufficiently improved. More preferably, it is 5000 mass ppm, More preferably, it is 2000 mass ppm, Most preferably, it is 1000 mass ppm. Moreover, as a preferable range, it is 20-2000 mass ppm, More preferably, it is 50-1000 mass ppm.
上記(メタ)アクリル酸のエステル類としては、(メタ)アクリル酸により形成されるものであればよく、マクロモノマーやプレポリマーを用いることもでき、例えば、以下のような化合物等が好適である。これらは1種又は2種以上を用いることができる。
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、イソプロピル(メタ)アクリレート、ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、sec−ブチル(メタ)アクリレート、t−ブチル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、メトキシエチル(メタ)アクリレート、メトキシポリエチレングリコール(メタ)アクリレート、N,N−ジメチルアミノエチル(メタ)アクリレート、イソボルニル(メタ)アクリレート等の単官能(メタ)アクリレート類;
The esters of (meth) acrylic acid may be those formed of (meth) acrylic acid, and macromonomers and prepolymers can also be used. For example, the following compounds are suitable. . These can use 1 type (s) or 2 or more types.
Methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, t-butyl (meth) Acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, methoxyethyl (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, isobornyl (meth) acrylate, etc. Monofunctional (meth) acrylates;
(メタ)アクリル酸2−ビニロキシエチル、(メタ)アクリル酸3−ビニロキシプロピル、(メタ)アクリル酸1−メチル−2−ビニロキシエチル、(メタ)アクリル酸2−ビニロキシプロピル、(メタ)アクリル酸4−ビニロキシブチル、(メタ)アクリル酸1−メチル−3−ビニロキシプロピル、(メタ)アクリル酸1−ビニロキシメチルプロピル、(メタ)アクリル酸2−メチル−3−ビニロキシプロピル、(メタ)アクリル酸3−メチル−3−ビニロキシプロピル、(メタ)アクリル酸1,1−ジメチル−2−ビニロキシエチル、(メタ)アクリル酸3−ビニロキシブチル、(メタ)アクリル酸1−メチル−2−ビニロキシプロピル、(メタ)アクリル酸2−ビニロキシブチル、(メタ)アクリル酸4−ビニロキシシクロヘキシル、(メタ)アクリル酸5−ビニロキシペンチル、(メタ)アクリル酸6−ビニロキシヘキシル、(メタ)アクリル酸4−ビニロキシメチルシクロヘキシルメチル、(メタ)アクリル酸3−ビニロキシメチルシクロヘキシルメチル、(メタ)アクリル酸2−ビニロキシメチルシクロヘキシルメチル、(メタ)アクリル酸m−ビニロキシメチルフェニルメチル、(メタ)アクリル酸o−ビニロキシメチルフェニルメチル、(メタ)アクリル酸p−ビニロキシメチルフェニルメチル、(メタ)アクリル酸2−(ビニロキシエトキシ)エチル、(メタ)アクリル酸2−(ビニロキシイソプロポキシ)エチル、(メタ)アクリル酸2−(ビニロキシエトキシ)プロピル、(メタ)アクリル酸2−(ビニロキシエトキシ)イソプロピル、(メタ)アクリル酸2−(ビニロキシイソプロポキシ)プロピル、(メタ)アクリル酸2−(ビニロキシイソプロポキシ)イソプロピル、(メタ)アクリル酸2−(ビニロキシエトキシエトキシ)エチル、(メタ)アクリル酸2−(ビニロキシエトキシイソプロポキシ)エチル、(メタ)アクリル酸2−(ビニロキシエトキシイソプロポキシ)プロピル、(メタ)アクリル酸2−(ビニロキシエトキシエトキシ)イソプロピル、(メタ)アクリル酸2−(ビニロキシエトキシイソプロポキシ)イソプロピル、(メタ)アクリル酸2−(ビニロキシエトキシエトキシエトキシ)エチル、(メタ)アクリル酸2−(ビニロキシイソプロポキシエトキシ)エチル、(メタ)アクリル酸2−(ビニロキシイソプロポキシイソプロポキシ)エチル、(メタ)アクリル酸2−(ビニロキシエトキシエトキシ)プロピル、(メタ)アクリル酸2−(ビニロキシイソプロポキシエトキシ)プロピル、(メタ)アクリル酸2−(ビニロキシイソプロポキシイソプロポキシ)プロピル、(メタ)アクリル酸2−(ビニロキシイソプロポキシエトキシ)イソプロピル、(メタ)アクリル酸2−(ビニロキシイソプロポキシイソプロポキシ)イソプロピル、(メタ)アクリル酸2−(ビニロキシエトキシエトキシエトキシエトキシ)エチル、(メタ)アクリル酸2−(イソプロポキシエトキシ)エチル、(メタ)アクリル酸2−(イソプロポキシエトキシエトキシ)エチル、(メタ)アクリル酸2−(イソプロポキシエトキシエトキシエトキシ)エチル、(メタ)アクリル酸2−(イソプロポキシエトキシエトキシエトキシエトキシ)エチル、(メタ)アクリル酸ポリエチレングリコールモノビニルエーテル、(メタ)アクリル酸ポリプロピレングリコールモノビニルエーテル等のビニルエーテル基含有(メタ)アクリル酸エステル類; (Meth) acrylic acid 2-vinyloxyethyl, (meth) acrylic acid 3-vinyloxypropyl, (meth) acrylic acid 1-methyl-2-vinyloxyethyl, (meth) acrylic acid 2-vinyloxypropyl, (meth) acrylic acid 4 -Vinyloxybutyl, 1-methyl-3-vinyloxypropyl (meth) acrylate, 1-vinyloxymethylpropyl (meth) acrylate, 2-methyl-3-vinyloxypropyl (meth) acrylate, (meth) acrylic acid 3-methyl-3-vinyloxypropyl, 1,1-dimethyl-2-vinyloxyethyl (meth) acrylate, 3-vinyloxybutyl (meth) acrylate, 1-methyl-2-vinyloxypropyl (meth) acrylate, ( (Meth) acrylic acid 2-vinyloxybutyl, (meth) acrylic acid 4-vinyloxycyclohexyl, (Meth) acrylic acid 5-vinyloxypentyl, (meth) acrylic acid 6-vinyloxyhexyl, (meth) acrylic acid 4-vinyloxymethylcyclohexylmethyl, (meth) acrylic acid 3-vinyloxymethylcyclohexylmethyl, (meth) 2-vinyloxymethylcyclohexylmethyl acrylate, m-vinyloxymethylphenylmethyl (meth) acrylate, o-vinyloxymethylphenylmethyl (meth) acrylate, p-vinyloxymethylphenylmethyl (meth) acrylate, ( 2- (vinyloxyethoxy) ethyl (meth) acrylate, 2- (vinyloxyisopropoxy) ethyl (meth) acrylate, 2- (vinyloxyethoxy) propyl (meth) acrylate, 2- (meth) acrylic acid 2- ( Vinyloxyethoxy) isopropyl, (meth) acrylic acid -(Vinyloxyisopropoxy) propyl, 2- (vinyloxyisopropoxy) isopropyl (meth) acrylate, 2- (vinyloxyethoxyethoxy) ethyl (meth) acrylate, 2- (vinyloxyethoxy) (meth) acrylate Isopropoxy) ethyl, (meth) acrylic acid 2- (vinyloxyethoxyisopropoxy) propyl, (meth) acrylic acid 2- (vinyloxyethoxyethoxy) isopropyl, (meth) acrylic acid 2- (vinyloxyethoxyisopropoxy) Isopropyl, 2- (vinyloxyethoxyethoxyethoxy) ethyl (meth) acrylate, 2- (vinyloxyisopropoxyethoxy) ethyl (meth) acrylate, 2- (vinyloxyisopropoxyisopropoxy) ethyl (meth) acrylate , (Meth) acrylic acid 2- ( Vinyloxyethoxyethoxy) propyl, (meth) acrylic acid 2- (vinyloxyisopropoxyethoxy) propyl, (meth) acrylic acid 2- (vinyloxyisopropoxyisopropoxy) propyl, (meth) acrylic acid 2- (vinyloxy) Isopropoxyethoxy) isopropyl, (meth) acrylic acid 2- (vinyloxyisopropoxyisopropoxy) isopropyl, (meth) acrylic acid 2- (vinyloxyethoxyethoxyethoxyethoxy) ethyl, (meth) acrylic acid 2- (isopropoxy) Ethoxy) ethyl, 2- (isopropoxyethoxyethoxyethoxy) ethyl (meth) acrylate, 2- (isopropoxyethoxyethoxyethoxy) ethyl (meth) acrylate, 2- (isopropoxyethoxyethoxyethoxyethoxy) (meth) acrylate ) Ethyl, (meth) Polyethylene glycol monovinyl ether acrylate, (meth) vinyl ether group-containing (meth) acrylic acid esters such as acrylic acid polypropylene glycol monovinyl ether;
(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸3−ヒドロキシプロピル、(メタ)アクリル酸1−メチル−2−ヒドロキシエチル、(メタ)アクリル酸2−ヒドロキシプロピル、(メタ)アクリル酸4−ヒドロキシブチル、(メタ)アクリル酸4−ヒドロキシシクロヘキシル、(メタ)アクリル酸5−ヒドロキシペンチル、(メタ)アクリル酸6−ヒドロキシヘキシル、(メタ)アクリル酸4−ヒドロキシメチルシクロヘキシルメチル、(メタ)アクリル酸p−ヒドロキシメチルフェニルメチル、(メタ)アクリル酸2−(ヒドロキシエトキシ)エチル、(メタ)アクリル酸2−(ヒドロキシエトキシエトキシ)エチル、(メタ)アクリル酸2−(ヒドロキシエトキシエトキシエトキシ)エチル、α−ヒドロキシメチルアクリル酸メチル、α−ヒドロキシメチルアクリル酸エチル、2−ヒドロキシ−3−フェノキシプロピル(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−ルプロパンモノ(メタ)アクリレート、EO変性トリメチロールプロパンモノ(メタ)アクリレート、PO変性トリメチロールプロパンモノ(メタ)アクリレ−ト、EO/PO変性トリメチロールプロパンモノ(メタ)アクリレート、α−ヒドロキシメチルアクリル酸、α−ヒドロキシメチルアクリル酸メチル等の単官能の水酸基含有(メタ)アクリレート類; (Meth) acrylic acid 2-hydroxyethyl, (meth) acrylic acid 3-hydroxypropyl, (meth) acrylic acid 1-methyl-2-hydroxyethyl, (meth) acrylic acid 2-hydroxypropyl, (meth) acrylic acid 4 -Hydroxybutyl, 4-hydroxycyclohexyl (meth) acrylate, 5-hydroxypentyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 4-hydroxymethylcyclohexylmethyl (meth) acrylate, (meth) acryl P-hydroxymethylphenylmethyl acid, 2- (hydroxyethoxy) ethyl (meth) acrylate, 2- (hydroxyethoxyethoxy) ethyl (meth) acrylate, 2- (hydroxyethoxyethoxyethoxy) ethyl (meth) acrylate, α-Hydroxymethyl Aqua Methyl oxalate, ethyl α-hydroxymethyl acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, glycerin mono (meth) acrylate, trimethylolpropane mono (meth) acrylate, EO-modified trimethylolpropane mono (meth) ) Monofunctional hydroxyl group content such as acrylate, PO-modified trimethylolpropane mono (meth) acrylate, EO / PO-modified trimethylolpropane mono (meth) acrylate, α-hydroxymethylacrylic acid, α-hydroxymethylmethylacrylate (Meth) acrylates;
エチレングリコールジ(メタ)アクリレート、1,3−プロパンジオールジ(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、1,3−ブタンジオールジ(メタ)アクリレート、1,2−ブタンジオールジ(メタ)アクリレート、2,3−ブタンジオールジ(メタ)アクリレート、1−メチル−1,3−プロパンジオールジ(メタ)アクリレート、2−メチル−1,3−プロパンジオールジ(メタ)アクリレート、2−メチル−1,2−プロパンジオールジ(メタ)アクリレート、1,5−ペンタンジオールジ(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、シクロヘキサン−1,4−ジオールジ(メタ)アクリレート、シクロヘキサン−1,4−ジメタノールジ(メタ)アクリレート、p−キシレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、ジプロピレングリコールジ(メタ)アクリレート、トリプロピレングリコールジ(メタ)アクリレート、テトラプロピレングリコールジ(メタ)アクリレート、エチレングリコールプロピレングリコール共重合体ジ(メタ)アクリレート等の二官能(メタ)アクリレート類; Ethylene glycol di (meth) acrylate, 1,3-propanediol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,3-butanediol di (meth) Acrylate, 1,2-butanediol di (meth) acrylate, 2,3-butanediol di (meth) acrylate, 1-methyl-1,3-propanediol di (meth) acrylate, 2-methyl-1,3- Propanediol di (meth) acrylate, 2-methyl-1,2-propanediol di (meth) acrylate, 1,5-pentanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, cyclohexane- 1,4-diol di (meth) acrylate, cyclohexane , 4-dimethanol di (meth) acrylate, p-xylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) Bifunctional (meth) acrylates such as acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, tetrapropylene glycol di (meth) acrylate, and ethylene glycol propylene glycol copolymer di (meth) acrylate ;
トリメチロールプロパントリ(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、グリセリントリ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、EO変性トリメチロールプロパントリ(メタ)アクリレート、PO変性トリメチロールプロパントリ(メタ)アクリレート、EO/PO変性トリメチロ−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へキサ(メタ)アクリレート等の多官能(メタ)アクリレート類; Trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, glycerol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, EO modified trimethylolpropane tri (meth) acrylate, PO modified trimethylolpropane Polyfunctional (meth) acrylates such as tri (meth) acrylate, EO / PO-modified trimethylolpropane tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate;
ジペンタエリスリトールペンタ(メタ)アクリレート、エチレンオキサイド付加ペンタエリスリトールテトラ(メタ)アクリレート、グリセリンジ(メタ)アクリレート、グリセリンアクリレートメタクリレート、トリメチロールプロパンジ(メタ)アクリレート、EO変性トリメチロールプロパンジ(メタ)アクリレート、PO変性トリメチロールプロパンジ(メタ)アクリレート、EO/PO変性トリメチロールプロパンジ(メタ)アクリレート等の多官能の水酸基含有(メタ)アクリレート類; Dipentaerythritol penta (meth) acrylate, ethylene oxide-added pentaerythritol tetra (meth) acrylate, glycerin di (meth) acrylate, glycerin acrylate methacrylate, trimethylolpropane di (meth) acrylate, EO-modified trimethylolpropane di (meth) acrylate Polyfunctional hydroxyl group-containing (meth) acrylates such as PO-modified trimethylolpropane di (meth) acrylate and EO / PO-modified trimethylolpropane di (meth) acrylate;
飽和若しくは不飽和の多塩基酸又はその無水物酸(例えば、マレイン酸、コハク酸、アジピン酸、フタル酸、イソフタル酸、テレフタル酸、テトラヒドロフタル酸等)と飽和又は不飽和の多価アルコール(例えば、エチレングリコール、プロピレングリコール、ネオペンチルグリコール、1,4−ブタンジオール、1,6−ヘキサンジオール、3−メチル−1,5−ペンタンジオール、ポリエチレングリコール、ポリプロピレングリコール、1,4−ジメチロールベンゼン、トリメチロールプロパン、ペンタエリスリトール等)と(メタ)アクリル酸との反応で得られるポリエステル(メタ)アクリレート類; Saturated or unsaturated polybasic acid or its anhydride acid (eg maleic acid, succinic acid, adipic acid, phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid etc.) and saturated or unsaturated polyhydric alcohol (eg , Ethylene glycol, propylene glycol, neopentyl glycol, 1,4-butanediol, 1,6-hexanediol, 3-methyl-1,5-pentanediol, polyethylene glycol, polypropylene glycol, 1,4-dimethylolbenzene, Polyester (meth) acrylates obtained by the reaction of (meth) acrylic acid with trimethylolpropane, pentaerythritol, etc .;
飽和又は不飽和の多価アルコール(例えば、エチレングリコール、ネオペンチルグリコール、ポリテトラメチレングリコール、ポリエステルポリオール、ポリカプロラクトンポリオール等)と有機ポリイソシアネート(例えば、トリレンジイソシアネート、イソホロンジイソシアネート、キシリレンジイソシアネート等)と水酸基含有(メタ)アクリレート(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、1,4−ブタンジオールモノ(メタ)アクリレート等)との反応で得られるウレタンポリ(メタ)アクリレート類; Saturated or unsaturated polyhydric alcohol (for example, ethylene glycol, neopentyl glycol, polytetramethylene glycol, polyester polyol, polycaprolactone polyol, etc.) and organic polyisocyanate (for example, tolylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, etc.) And urethane-containing poly (meth) acrylate (for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 1,4-butanediol mono (meth) acrylate, etc.)) (Meth) acrylates;
ポリシロキサンと(メタ)アクリル酸との反応によって得られるポリシロキサンポリ(メタ)アクリレート類; Polysiloxane poly (meth) acrylates obtained by reaction of polysiloxane with (meth) acrylic acid;
ポリアミドと(メタ)アクリル酸との反応によって得られるポリアミドポリ(メタ)アクリレート類; Polyamide poly (meth) acrylates obtained by reaction of polyamide with (meth) acrylic acid;
ビニルエーテル基含有(メタ)アクリル酸エステル類等とカチオン重合性化合物(例えば、ビニルエーテル類、アルキレンオキサイド類、グリシジルエーテル類等)との反応によって得られる(メタ)アクリロイル基ペンダントポリマー類; (Meth) acryloyl group pendant polymers obtained by reaction of vinyl ether group-containing (meth) acrylic acid esters and the like with cationically polymerizable compounds (for example, vinyl ethers, alkylene oxides, glycidyl ethers, etc.);
エポキシ樹脂(例えば、フェノールノボラックエポキシ樹脂、クレゾールノボラックエポキシ樹脂、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、トリスフェノールメタン型エポキシ樹脂、ポリブタンジエン変性エポキシ樹脂、脂環式エポキシ樹脂、臭素化フェノールノボラックエポキシ樹脂、臭素化ビスフェノールA型エポキシ樹脂、アミノ基含有エポキシ樹脂等)と(メタ)アクリル酸との反応で得られるエポキシポリ(メタ)アクリレート類; Epoxy resins (for example, phenol novolac epoxy resins, cresol novolac epoxy resins, bisphenol A type epoxy resins, bisphenol F type epoxy resins, trisphenol methane type epoxy resins, polybutanediene modified epoxy resins, alicyclic epoxy resins, brominated phenols Novolac epoxy resins, brominated bisphenol A type epoxy resins, amino group-containing epoxy resins, etc.) and epoxy poly (meth) acrylates obtained by reaction of (meth) acrylic acid;
上記エポキシ(メタ)アクリレートと多塩基酸無水物(例えば、無水マレイン酸、無水コハク酸、無水フタル酸、テトラヒドロ無水フタル酸、ヘキサヒドロ無水フタル酸等)との反応で得られるカルボン酸変性エポキシ(メタ)アクリレート類。
これらの中でも、単官能(メタ)アクリレート類、ビニルエーテル基含有(メタ)アクリル酸エステル類、単官能の水酸基含有(メタ)アクリレート類、多官能(メタ)アクリレート類、多官能の水酸基含有(メタ)アクリレート類等が好ましい。
Carboxylic acid-modified epoxy (meta) obtained by reaction of the above epoxy (meth) acrylate with a polybasic acid anhydride (for example, maleic anhydride, succinic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, etc.) ) Acrylates.
Among these, monofunctional (meth) acrylates, vinyl ether group-containing (meth) acrylic acid esters, monofunctional hydroxyl group-containing (meth) acrylates, polyfunctional (meth) acrylates, polyfunctional hydroxyl group-containing (meth) Acrylates are preferred.
上記(メタ)アクリル酸及び/又はそのエステル類としてはまた、その他の重合性単量体を含有していてもよく、例えば、以下のような化合物等が好適である。これらは1種又は2種以上を用いることができる。
メチルビニルエーテル、エチルビニルエーテル、ブチルビニルエーテル、2−エチルヘキシルビニルエーテル、シクロヘキシルビニルエーテル、メトキシエチルビニルエーテル、メトキシポリエチレングリコールビニルエーテル等の単官能ビニルエーテル類;
The (meth) acrylic acid and / or esters thereof may also contain other polymerizable monomers. For example, the following compounds are suitable. These can use 1 type (s) or 2 or more types.
Monofunctional vinyl ethers such as methyl vinyl ether, ethyl vinyl ether, butyl vinyl ether, 2-ethylhexyl vinyl ether, cyclohexyl vinyl ether, methoxyethyl vinyl ether, methoxypolyethylene glycol vinyl ether;
2−ヒドロキシエチルビニルエーテル、3−ヒドロキシプロピルビニルエーテル、1−メチル−2−ヒドロキシエチルビニルエーテル、2−ヒドロキシプロピルビニルエーテル、4−ヒドロキシブチルビニルエーテル、4−ヒドロキシシクロヘキシルビニルエーテル、5−ヒドロキシペンチルビニルエーテル、6−ヒドロキシヘキシルビニルエーテル、4−ヒドロキシメチルシクロヘキシルメチルビニルエーテル、p−ヒドロキシメチルフェニルメチルビニルエーテル、2−(ヒドロキシエトキシ)エチルビニルエーテル、2−(ヒドロキシエトキシエトキシ)エチルビニルエーテル、2−(ヒドロキシエトキシエトキシエトキシ)エチルビニルエーテル等の単官能の水酸基含有ビニルエーテル類; 2-hydroxyethyl vinyl ether, 3-hydroxypropyl vinyl ether, 1-methyl-2-hydroxyethyl vinyl ether, 2-hydroxypropyl vinyl ether, 4-hydroxybutyl vinyl ether, 4-hydroxycyclohexyl vinyl ether, 5-hydroxypentyl vinyl ether, 6-hydroxyhexyl Vinyl ether, 4-hydroxymethylcyclohexylmethyl vinyl ether, p-hydroxymethylphenylmethyl vinyl ether, 2- (hydroxyethoxy) ethyl vinyl ether, 2- (hydroxyethoxyethoxy) ethyl vinyl ether, 2- (hydroxyethoxyethoxyethoxy) ethyl vinyl ether, etc. Functional hydroxyl-containing vinyl ethers;
エチレングリコールジビニルエーテル、1,3−プロパンジオールジビニルエーテル、プロピレングリコールジビニルエーテル、1,4−ブタンジオールジビニルエーテル、1,3−ブタンジオールジビニルエーテル、1,2−ブタンジオールジビニルエーテル、2,3−ブタンジオールジビニルエーテル、1−メチル−1,3−プロパンジオールジビニルエーテル、2−メチル−1,3−プロパンジオールジビニルエーテル、2−メチル−1,2−プロパンジオールジビニルエーテル、1,5−ペンタンジオールジビニルエーテル、1,6−ヘキサンジオールジビニルエーテル、シクロヘキサン−1,4−ジオールジビニルエーテル、シクロヘキサン−1,4−ジメタノールジビニルエーテル、p−キシレングリコールジビニルエーテル、ジエチレングリコールジビニルエーテル、トリエチレングリコールジビニルエーテル、テトラエチレングリコールジビニルエーテル、ポリエチレングリコールジビニルエーテル、ジプロピレングリコールジビニルエーテル、トリプロピレングリコールジビニルエーテル、テトラプロピレングリコールジビニルエーテル、ポリプロピレングリコールジビニルエーテル、エチレングリコールプロピレングリコール共重合体ジビニルエーテル等のジビニルエーテル類; Ethylene glycol divinyl ether, 1,3-propanediol divinyl ether, propylene glycol divinyl ether, 1,4-butanediol divinyl ether, 1,3-butanediol divinyl ether, 1,2-butanediol divinyl ether, 2,3- Butanediol divinyl ether, 1-methyl-1,3-propanediol divinyl ether, 2-methyl-1,3-propanediol divinyl ether, 2-methyl-1,2-propanediol divinyl ether, 1,5-pentanediol Divinyl ether, 1,6-hexanediol divinyl ether, cyclohexane-1,4-diol divinyl ether, cyclohexane-1,4-dimethanol divinyl ether, p-xylene glycol divinyl ether, Ethylene glycol divinyl ether, triethylene glycol divinyl ether, tetraethylene glycol divinyl ether, polyethylene glycol divinyl ether, dipropylene glycol divinyl ether, tripropylene glycol divinyl ether, tetrapropylene glycol divinyl ether, polypropylene glycol divinyl ether, ethylene glycol propylene glycol Divinyl ethers such as polymer divinyl ether;
トリメチロールプロパントリビニルエーテル、ジトリメチロールプロパンテトラビニルエーテル、グリセリントリビニルエーテル等の多官能ビニルエーテル類; Polyfunctional vinyl ethers such as trimethylolpropane trivinyl ether, ditrimethylolpropane tetravinyl ether, glycerin trivinyl ether;
ジペンタエリスリトールペンタビニルエーテル、エチレンオキサイド付加ペンタエリスリトールテトラビニルエーテル等の多官能の水酸基含有ビニルエーテル類; Polyfunctional hydroxyl-containing vinyl ethers such as dipentaerythritol pentavinyl ether and ethylene oxide-added pentaerythritol tetravinyl ether;
3−メチル−3−フェノキシメチルオキセタン、3−エチル−3−フェノキシメチルオキセタン、3−エチル−3−(2−エチルヘキシロキシメチル)オキセタン等の単官能脂環式エーテル化合物類; Monofunctional alicyclic ether compounds such as 3-methyl-3-phenoxymethyloxetane, 3-ethyl-3-phenoxymethyloxetane, 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane;
グリシドール、3−メチル−3−ヒドロキシメチルオキセタン、3−エチル−3−ヒドロキシメチルオキセタン等の単官能の水酸基含有脂環式エーテル化合物類; Monofunctional hydroxyl group-containing alicyclic ether compounds such as glycidol, 3-methyl-3-hydroxymethyloxetane, 3-ethyl-3-hydroxymethyloxetane;
ジ[1−メチル(3−オキセタニル)]メチルエーテル、ジ[1−エチル(3−オキセタニル)]メチルエーテル、1,4−ビス{[(3−エチル−3−オキセタニル)メトキシ]メチル}ベンゼン、ビス{4−[(3−エチル−3−オキセタニル)メトキシ]メチル}ベンジルエーテル等の多官能脂環式エーテル化合物類; Di [1-methyl (3-oxetanyl)] methyl ether, di [1-ethyl (3-oxetanyl)] methyl ether, 1,4-bis {[(3-ethyl-3-oxetanyl) methoxy] methyl} benzene, Polyfunctional alicyclic ether compounds such as bis {4-[(3-ethyl-3-oxetanyl) methoxy] methyl} benzyl ether;
メチルグリシジルエーテル、エチルグリシジルエーテル、ブチルグリシジルエーテル、2−エチルヘキシルグリシジルエーテル、シクロヘキシルグリシジルエーテル、メトキシエチルグリシジルエーテル等の単官能エポキシ化合物類; Monofunctional epoxy compounds such as methyl glycidyl ether, ethyl glycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, cyclohexyl glycidyl ether, methoxyethyl glycidyl ether;
エチレングリコ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、ポリエチレングリコールジグリシジルエーテル、ブチレングリコールジグリシジルエーテル、ヘキサンジオールジグリシジルエーテル、ビスフェノールAアルキレンオキサイドジグリシジルエーテル、ビスフェノールFアルキレンオキサイドジグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、グリセリントリグリシジルエーテル等の多官能エポキシ化合物類; Ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, butylene glycol diglycidyl ether, hexanediol diglycidyl ether, bisphenol A alkylene oxide diglycidyl ether, bisphenol F alkylene oxide diglycidyl ether, trimethylolpropane triglycidyl Polyfunctional epoxy compounds such as ether and glycerin triglycidyl ether;
ジペンタエリスリトールペンタグリシジルエーテル、エチレンオキサイド付加ペンタエリスリトールテトラグリシジルエーテル等の多官能の水酸基含有エポキシ化合物類; Polyfunctional hydroxyl-containing epoxy compounds such as dipentaerythritol pentaglycidyl ether and ethylene oxide-added pentaerythritol tetraglycidyl ether;
N,N−ジメチル(メタ)アクリルアミド、N−メチロール(メタ)アクリルアミド、アクリロイルモルホリン等の単官能(メタ)アクリルアミド類; Monofunctional (meth) acrylamides such as N, N-dimethyl (meth) acrylamide, N-methylol (meth) acrylamide, acryloylmorpholine;
N−ビニルピロリドン、N−ビニルカプロラクタム、N−ビニルホルムアミド、N−ビニルアセトアミド、N−ビニルカルバゾール等の単官能N−ビニル化合物類; Monofunctional N-vinyl compounds such as N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylformamide, N-vinylacetamide, N-vinylcarbazole;
スチレン、α−メチルスチレン、酢酸ビニル等の単官能ビニル化合物類; Monofunctional vinyl compounds such as styrene, α-methylstyrene, vinyl acetate;
無水マレイン酸、マレイン酸、マレイン酸ジメチル、マレイン酸ジエチル、フマル酸、フマル酸ジメチル、フマル酸ジエチル、フマル酸モノメチル、フマル酸モノエチル、無水イタコン酸、イタコン酸、イタコン酸ジメチル、メチレンマロン酸、メチレンマロン酸ジメチル、桂皮酸、桂皮酸メチル、クロトン酸、クロトン酸メチル等の単官能α,β−不飽和化合物類; Maleic anhydride, maleic acid, dimethyl maleate, diethyl maleate, fumaric acid, dimethyl fumarate, diethyl fumarate, monomethyl fumarate, monoethyl fumarate, itaconic anhydride, itaconic acid, dimethyl itaconate, methylenemalonic acid, methylene Monofunctional α, β-unsaturated compounds such as dimethyl malonate, cinnamic acid, methyl cinnamate, crotonic acid, methyl crotonic acid;
ジビニルベンゼン等の多官能ビニル化合物類。
これらの中でも、単官能ビニルエーテル類、単官能の水酸基含有ビニルエーテル類、多官能ビニルエーテル類、単官能(メタ)アクリルアミド類、単官能N−ビニル化合物類等が好ましい。
Polyfunctional vinyl compounds such as divinylbenzene.
Among these, monofunctional vinyl ethers, monofunctional hydroxyl group-containing vinyl ethers, polyfunctional vinyl ethers, monofunctional (meth) acrylamides, monofunctional N-vinyl compounds, and the like are preferable.
上記その他の重合性単量体の含有量は、求められる物性により適宜選択すればよい。具体的には、本発明の(メタ)アクリル酸及び/又はそのエステル類の総量100質量部に対して、下限値が0.01質量部が好ましい。より好ましくは、0.1質量部であり、より好ましくは、10質量部であり、更に好ましくは、20質量部であり、特に好ましくは、30質量部であり、最も好ましくは、50質量部である。上限値としては、500質量部が好ましい。より好ましくは、400質量部であり、更に好ましくは、300質量部であり、特に好ましくは、200質量部であり、最も好ましくは、100質量部である。また、好ましい範囲としては、0.01〜200質量部であり、より好ましくは、0.01〜100質量部である。 What is necessary is just to select suitably content of the said other polymerizable monomer by the physical property calculated | required. Specifically, the lower limit is preferably 0.01 parts by mass with respect to 100 parts by mass of the total amount of (meth) acrylic acid and / or esters thereof of the present invention. More preferably, it is 0.1 mass part, More preferably, it is 10 mass parts, More preferably, it is 20 mass parts, Especially preferably, it is 30 mass parts, Most preferably, it is 50 mass parts is there. As an upper limit, 500 mass parts is preferable. More preferably, it is 400 parts by mass, still more preferably 300 parts by mass, particularly preferably 200 parts by mass, and most preferably 100 parts by mass. Moreover, as a preferable range, it is 0.01-200 mass parts, More preferably, it is 0.01-100 mass parts.
本発明の(メタ)アクリル酸及び/又はそのエステル類においては、光重合開始剤を含有していてもよい。光重合開始剤を含有することにより、光硬化用途に有用な組成物とできることになる。このように、本発明の(メタ)アクリル酸及び/又はそのエステル類を含んでなる光硬化用組成物もまた、本発明の好ましい実施形態の一つである。また必要に応じて、光増感剤、光重合促進剤等を用いることも可能である。 The (meth) acrylic acid and / or esters thereof of the present invention may contain a photopolymerization initiator. By containing a photopolymerization initiator, a composition useful for photocuring applications can be obtained. Thus, the photocurable composition comprising the (meth) acrylic acid and / or ester thereof of the present invention is also one of the preferred embodiments of the present invention. Further, if necessary, a photosensitizer, a photopolymerization accelerator and the like can be used.
上記光重合開始剤としては、例えば、光ラジカル重合開始剤や光カチオン重合開始剤等を挙げることができる。
上記光ラジカル重合開始剤としては、下記の化合物が好適である。
ジエトキシアセトフェノン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、ベンジルジメチルケタール、4−(2−ヒドロキシエトキシ)フェニル−(2−ヒドロキシ−2−プロピル)ケトン、1−ヒドロキシシクロヘキシルフェニルケトン、2−メチル−2−モルホリノ(4−チオメチルフェニル)プロパン−1−オン、2−ベンジルー2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン、2−ヒドロキシ−2−メチル−1−[4−(1−メチルビニル)フェニル]プロパノンオリゴマー等のアセトフェノン類;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、ベンゾインイソプロピルエーテル、ベンゾインイソブチルエーテル等のベンゾイン類;ベンゾフェノン、o−ベンゾイル安息香酸メチル、4−フェニルベンゾフェノン、4−ベンゾイル−4′−メチル−ジフェニルサルファイド、3,3′,4,4′−テトラ(t−ブチルパーオキシルカルボニル)ベンゾフェノン、2,4,6−トリメチルベンゾフェノン、4−ベンゾイル−N,N−ジメチル−N−[2−(1−オキソ−2−プロペニルオキシ)エチル]ベンゼンメタナミニウムブロミド、(4−ベンゾイルベンジル)トリメチルアンモニウムクロリド等のベンゾフェノン類;2−イソプロピルチオキサントン、4−イソプロピルチオキサントン、2,4−ジエチルチオキサントン、2,4−ジクロロチオキサントン、1−クロロ−4−プロポキシチオキサントン、2−(3−ジメチルアミノ−2−ヒドロキシ)−3,4−ジメチル−9H−チオキサントン−9−オンメソクロリド等のチオキサントン類。
これらの中でも、アセトフェノン類、ベンゾフェノン類、アシルフォスフィンオキサイド類が好ましい。より好ましくは、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、2−メチル2−モルホリノ(4−チオメチルフェニル)プロパン−1オンである。
Examples of the photopolymerization initiator include a photoradical polymerization initiator and a photocationic polymerization initiator.
As the radical photopolymerization initiator, the following compounds are suitable.
Diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethyl ketal, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl Phenylketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone, 2-hydroxy-2-methyl-1 Acetophenones such as [4- (1-methylvinyl) phenyl] propanone oligomer; benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, o-benzoyl Methyl perfume, 4-phenylbenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, 3,3 ', 4,4'-tetra (t-butylperoxylcarbonyl) benzophenone, 2,4,6-trimethylbenzophenone Benzophenones such as 4-benzoyl-N, N-dimethyl-N- [2- (1-oxo-2-propenyloxy) ethyl] benzenemethananium bromide, (4-benzoylbenzyl) trimethylammonium chloride; Isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, 2- (3-dimethylamino-2-hydroxy) -3,4-dimethyl- 9H-thioxanthone-9 Thioxanthones such as Onmesokurorido.
Among these, acetophenones, benzophenones, and acyl phosphine oxides are preferable. More preferred are 2-hydroxy-2-methyl-1-phenylpropan-1-one and 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one.
上記光カチオン重合開始剤としては、下記の化合物が好適である。
トリフェニルスルホニウムヘキサフルオロホスフェート、トリフェニルスルホニウムヘキサフルオロアンチモネート等のアリールスルフォニウム塩;ジフェニルヨードニウムヘキサフルオロアンチモネート、ジフェニルヨードニウムヘキサフルオロホスフェート、(トリルクミル)ヨードニウムテトラキス(ペンタフルオロフェニル)ボレート等のアリールヨウドニウム塩;フェニルジアゾニウムテトラフルオロボレート等のアリールジアゾニウム塩。
これらの中でも、アリールスルフォニウム塩、ジアゾニウム塩が好ましい。より好ましくは、(トリルクミル)ヨードニウムテトラキス(ペンタフルオロフェニル)ボレートである。
As the photocationic polymerization initiator, the following compounds are suitable.
Arylsulfonium salts such as triphenylsulfonium hexafluorophosphate and triphenylsulfonium hexafluoroantimonate; aryliodines such as diphenyliodonium hexafluoroantimonate, diphenyliodonium hexafluorophosphate, (tolylcumyl) iodonium tetrakis (pentafluorophenyl) borate Nium salts; aryldiazonium salts such as phenyldiazonium tetrafluoroborate.
Among these, arylsulfonium salts and diazonium salts are preferable. More preferred is (tolylcumyl) iodonium tetrakis (pentafluorophenyl) borate.
上記光重合開始剤の使用量としては、酸化防止剤を含まない(メタ)アクリル酸及び/又はエステル類に対して、下限値としては0.05質量%であることが好ましい。0.05質量%未満であると、充分に光硬化性が向上しないおそれがある。より好ましくは、0.1質量%であり、更に好ましくは、0.2質量%である。上限値としては、20質量%であることが好ましい。20質量%を超えると、硬化物物性を充分に向上できないおそれがある。より好ましくは、15質量%であり、更に好ましくは、10質量%である。 As the usage-amount of the said photoinitiator, it is preferable that it is 0.05 mass% as a lower limit with respect to (meth) acrylic acid and / or esters which do not contain antioxidant. If it is less than 0.05% by mass, the photocurability may not be sufficiently improved. More preferably, it is 0.1 mass%, More preferably, it is 0.2 mass%. As an upper limit, it is preferable that it is 20 mass%. When it exceeds 20 mass%, there exists a possibility that hardened | cured material physical property cannot fully be improved. More preferably, it is 15 mass%, More preferably, it is 10 mass%.
本発明の(メタ)アクリル酸及び/又はそのエステル類や光硬化用組成物は、上記の酸化防止剤以外に、その他の添加剤を含有していてもよく、例えば、無機充填剤、非反応性樹脂(例えば、アクリルポリマー、ポリエステル、ポリウレタン、ポリスチレン、ポリ塩化ビニル等)、有機溶剤、着色顔料、可塑剤、紫外線吸収剤、上記以外の酸化防止剤、艶消し剤、染料、消泡剤、レベリング剤、帯電防止剤、分散剤、スリップ剤、表面改質剤、揺変化剤、揺変助剤等を含有させることができる。これらはそれぞれ、1種又は2種以上を用いることができる。 The (meth) acrylic acid and / or its esters and photocuring composition of the present invention may contain other additives in addition to the above-mentioned antioxidants. Resin (for example, acrylic polymer, polyester, polyurethane, polystyrene, polyvinyl chloride, etc.), organic solvent, coloring pigment, plasticizer, ultraviolet absorber, antioxidants other than the above, matting agent, dye, antifoaming agent, Leveling agents, antistatic agents, dispersants, slip agents, surface modifiers, thixotropic agents, thixotropic aids, and the like can be included. Each of these can be used alone or in combination of two or more.
本発明の光硬化用組成物は、電磁波、紫外線、可視光線、赤外線、電子線、ガンマー線等の活性エネルギ−線により硬化することができる。
上記紫外線による硬化の場合、波長150〜450nmの範囲内の光を含む光源を用いることが好ましい。このような光源としては、太陽光線、低圧水銀灯、高圧水銀灯、超高圧水銀灯、メタルハライド灯、ガリウム灯、キセノン灯、カーボンアーク灯等が好適である。これらの光源と共に、赤外線、遠赤外線、熱風、高周波加熱等による熱の併用も可能である。この場合、本発明の光硬化用組成物においては光重合開始剤以外に、熱重合開始剤、熱重合促進剤等を用いることが可能である。
上記電子線による硬化は、加速電圧の下限が、好ましくは10kV以上、より好ましくは20kV以上、更に好ましくは30kV以上、その上限が、好ましくは500kV以下、より好ましくは300kV以下、更に好ましくは200kV以下である電子線を用いればよい。また、照射量は、その下限が、2kGy以上が好ましく、3kGy以上がより好ましく、5kGy以上が更に好ましく、その上限が、500kGy以下が好ましく、300kGy以下がより好ましく、200kGy以下が更に好ましい。電子線と共に、赤外線、遠赤外線、熱風、高周波加熱等による熱の併用も可能である。
このように本発明の光硬化用組成物を光硬化させてなる硬化物は、硬化物物性に優れ、黄変がほとんど起こらず、種々の用途に好適なものであり、このような硬化物もまた、本発明の好ましい実施形態の一つである。
The photocurable composition of the present invention can be cured by active energy rays such as electromagnetic waves, ultraviolet rays, visible rays, infrared rays, electron beams, and gamma rays.
In the case of curing with ultraviolet rays, it is preferable to use a light source including light within a wavelength range of 150 to 450 nm. As such a light source, a solar ray, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a metal halide lamp, a gallium lamp, a xenon lamp, a carbon arc lamp, or the like is preferable. Together with these light sources, it is possible to use heat by infrared rays, far infrared rays, hot air, high-frequency heating or the like. In this case, in the photocurable composition of the present invention, it is possible to use a thermal polymerization initiator, a thermal polymerization accelerator and the like in addition to the photopolymerization initiator.
In the curing by the electron beam, the lower limit of the acceleration voltage is preferably 10 kV or more, more preferably 20 kV or more, still more preferably 30 kV or more, and the upper limit thereof is preferably 500 kV or less, more preferably 300 kV or less, still more preferably 200 kV or less. What is necessary is just to use the electron beam which is. The lower limit of the irradiation amount is preferably 2 kGy or more, more preferably 3 kGy or more, further preferably 5 kGy or more, and the upper limit is preferably 500 kGy or less, more preferably 300 kGy or less, and further preferably 200 kGy or less. Along with an electron beam, it is possible to use heat by infrared rays, far infrared rays, hot air, high-frequency heating or the like.
Thus, a cured product obtained by photocuring the photocurable composition of the present invention is excellent in cured product properties, hardly causes yellowing, and is suitable for various applications. Moreover, it is one of the preferable embodiments of the present invention.
本発明の(メタ)アクリル酸及び/又はそのエステル類や光硬化用組成物は、接着剤、粘着剤、生体材料、歯科材料、光学部材、情報記録材料、光ファイバー用材料、レジスト材料、絶縁体、封止材、インク、インクジェット用インク、印刷インク、スクリーン印刷インク、塗料、注型材料、化粧板、WPC、被覆材、感光性樹脂版、ドライフィルム、ライニング材、土木建築材料、パテ、補修材、床材、舗装材ゲルコート、オーバーコート、ハンドレイアップ・スプレーアップ・引抜成形・フィラメントワインディング・SMC・BMC等の成形材料、シート、プラズマディスプレイ隔壁、高分子固体電解質等の種々の用途に用いることができる有用なものである。 The (meth) acrylic acid and / or its esters and photocuring compositions of the present invention are adhesives, pressure-sensitive adhesives, biomaterials, dental materials, optical members, information recording materials, optical fiber materials, resist materials, insulators. , Sealing material, ink, inkjet ink, printing ink, screen printing ink, paint, casting material, decorative board, WPC, coating material, photosensitive resin plate, dry film, lining material, civil engineering building material, putty, repair Materials, flooring materials, paving materials, gel coats, overcoats, molding materials such as hand lay-up, spray-up, pultrusion, filament winding, SMC and BMC, sheets, plasma display partition walls, polymer solid electrolytes, etc. It can be useful things.
本発明の(メタ)アクリル酸及び/又はそのエステル類は、上述の構成よりなり、保存安定性を維持したまま、光硬化性が向上されたものであり、黄変を起こさない硬化物を提供することができるものである。また、このような(メタ)アクリル酸及び/又はそのエステル類を含有する光硬化用組成物やその硬化物も有用なものである。 The (meth) acrylic acid and / or esters thereof according to the present invention have the above-described structure, and are provided with a cured product that has improved photocurability while maintaining storage stability and does not cause yellowing. Is something that can be done. Moreover, the photocurable composition containing such (meth) acrylic acid and / or its ester, and its hardened | cured material are also useful.
以下に実施例を掲げて本発明を更に詳細に説明するが、本発明はこれらの実施例のみに限定されるものではない。なお、特に断りのない限り、「部」は「質量部」を、「ppm」は「質量ppm」を意味するものとする。 The present invention will be described in more detail with reference to the following examples. However, the present invention is not limited to these examples. Unless otherwise specified, “part” means “part by mass” and “ppm” means “mass ppm”.
実施例1〜4及び比較例1〜5
表1及び表2に示す組成物を調製し、下記に示す方法で試験を行った。結果を表1及び表2に示す。なお、樹脂Aは、下記のように合成した。
[樹脂A合成例](ウレタンアクリレート(樹脂A)の合成)
撹拌器、温度計、精留塔及びガス導入管を備え付けた1リットルの四つ口フラスコに、トリレンジイソシアネート348部及びジブチル錫ジラウレート0.3部を加えて窒素気流下40℃に保ち、同温度でヒドロキシプロピルアクリレート260部を2時間かけて滴下し、次いで同温度でジプロピレングリコール141部を2時間かけて滴下し、更に同温度にて5時間反応させ、ウレタンアクリレートを得た。得られたウレタンアクリレートを樹脂Aとする。
Examples 1-4 and Comparative Examples 1-5
The compositions shown in Table 1 and Table 2 were prepared and tested by the method shown below. The results are shown in Tables 1 and 2. Resin A was synthesized as follows.
[Resin A Synthesis Example] (Synthesis of Urethane Acrylate (Resin A))
To a 1 liter four-necked flask equipped with a stirrer, thermometer, rectification column and gas introduction tube, add 348 parts of tolylene diisocyanate and 0.3 part of dibutyltin dilaurate, and maintain at 40 ° C. under a nitrogen stream. At a temperature, 260 parts of hydroxypropyl acrylate was added dropwise over 2 hours, then 141 parts of dipropylene glycol was added dropwise at the same temperature over 2 hours, and further reacted at the same temperature for 5 hours to obtain urethane acrylate. The obtained urethane acrylate is referred to as Resin A.
〔安定性〕
50mlガラス容器に組成物25mlを添加し、100℃のオイルバス中にて空気雰囲気下で24時間撹拌した。24時間後にテトラヒドロフランをキャリアとするHLC−8120GPC型ゲル透過クロマトグラフィー(東ソー社製;以下「GPC」と呼ぶ)により分析し、高分子量物の生成の有無を確認した。なお、比較例2は、6時間でゲル化した(THFに不溶)。
〔残留モノマー量測定〕
残存モノマーによる発熱量を測定し、残留モノマー量とした。
調製した組成物を1.0J/cm2のエネルギーでUV(紫外線)を照射して硬化させて、厚み370μmのフィルムを作製した。UV照射は、ウシオ電機社製のPM25C−100を用いた。そのフィルム表面を、PET(ポリエチレンテレフタレート)フィルム(250μm)でカバーした。
得られたフィルムを、Mac Science社製のDSC−3100型DSC測定装置を用いて発熱量を測定した。昇温スピードは、25℃から300℃まで10℃/分とし、発熱ピ−クの面積より発熱量を計算した。
〔Stability〕
25 ml of the composition was added to a 50 ml glass container, and stirred in an oil bath at 100 ° C. under an air atmosphere for 24 hours. After 24 hours, analysis was performed by HLC-8120 GPC gel permeation chromatography (manufactured by Tosoh Corporation; hereinafter referred to as “GPC”) using tetrahydrofuran as a carrier, and the presence or absence of high molecular weight product was confirmed. Comparative Example 2 gelled in 6 hours (insoluble in THF).
(Residual monomer amount measurement)
The amount of heat generated by the residual monomer was measured and used as the residual monomer amount.
The prepared composition was cured by irradiating UV (ultraviolet rays) with an energy of 1.0 J / cm 2 to produce a film having a thickness of 370 μm. For UV irradiation, PM25C-100 manufactured by USHIO INC. Was used. The film surface was covered with a PET (polyethylene terephthalate) film (250 μm).
The calorific value of the obtained film was measured using a DSC-3100 type DSC measuring device manufactured by Mac Science. The heating rate was 10 ° C./min from 25 ° C. to 300 ° C., and the heat generation amount was calculated from the area of the heat generating peak.
〔指触乾燥性〕
上記残留モノマー量測定と同様に、厚みが370μmのフィルムを作製した。該フィルムに表面カバーはしなかった。ウシオ電機社製のPM25C−100を用いて、0.1J/cm2ごとにフィルムにUV照射を行い、表面乾燥性を指触で評価した。評価は以下のように行った。
×=未硬化、△=指紋がつく、〇=タックフリー
なお、右上の「+」及び「−」は、各評価内における優劣を表す。
〔YI値測定〕
組成物を1.0J/cm2で硬化させて得られた硬化物について、JIS K7103に準拠して測定した。色差計は、日本電色工業社製Σ90型を用いた。
[Dry touch]
A film having a thickness of 370 μm was produced in the same manner as the residual monomer amount measurement. The film was not surface covered. Using PM25C-100 manufactured by USHIO INC., The film was irradiated with UV every 0.1 J / cm 2 and the surface drying property was evaluated by touch. Evaluation was performed as follows.
× = Uncured, Δ = Fingerprint attached, ○ = Tack free Note that “+” and “−” in the upper right represent superiority or inferiority in each evaluation.
[YI value measurement]
The cured product obtained by curing the composition at 1.0 J / cm 2 was measured according to JIS K7103. As the color difference meter, Σ90 type manufactured by Nippon Denshoku Industries Co., Ltd. was used.
表1及び表2について以下に説明する。
VEEA:アクリル酸2−(ビニロキシエトキシ)エチル
TMPTA:トリメチロールプロパントリアクリレート
IBA:イソブチルアクリレート
AO30:旭電化工業社製「アデカスタブAO30」(物質名:1,1,3−トリス(2−メチル−4−ヒドロキシ−5−t−ブチルフェニル)ブタン)
AO40:旭電化工業社製「アデカスタブAO40」(物質名:4,4−ブチリデンビス(3−メチル−6−t−ブチルフェノール))
MEHQ:メトキシヒドロキノン
HQ:ハイドロキノン
907:チバスペシャリティー・ケミカルズ社製「イルガキュア907」(物質名:2−メチル−2−モルホリノ−1−(4−メチルチオフェニル)プロパン−1−オン)
184:チバスペシャリティー・ケミカルズ社製「イルガキュア184」(物質名:1−ヒドロキシシクロへキシルフェニルケトン)
Tables 1 and 2 will be described below.
VEEA: 2- (vinyloxyethoxy) ethyl acrylate TMPTA: trimethylolpropane triacrylate IBA: isobutyl acrylate AO30: “Adekastab AO30” manufactured by Asahi Denka Kogyo Co., Ltd. (substance name: 1,1,3-tris (2-methyl- 4-hydroxy-5-tert-butylphenyl) butane)
AO40: “Adeka Stub AO40” manufactured by Asahi Denka Kogyo Co., Ltd. (substance name: 4,4-butylidenebis (3-methyl-6-tert-butylphenol))
MEHQ: Methoxyhydroquinone HQ: Hydroquinone 907: “Irgacure 907” manufactured by Ciba Specialty Chemicals (substance name: 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one)
184: “Irgacure 184” (substance name: 1-hydroxycyclohexyl phenyl ketone) manufactured by Ciba Specialty Chemicals
Claims (8)
該酸化防止剤は、少なくともフェノール性水酸基を持つフェニル基を有し、
該フェノール性水酸基が結合している炭素原子に隣接する炭素原子の一方に水素原子が結合し、他方にアルキル基が結合する構造を有する、下記一般式(1):
該(メタ)アクリル酸エステル類は、ビニルエーテル基含有(メタ)アクリル酸エステル類、多官能(メタ)アクリレート類、ビニルエーテル基含有(メタ)アクリル酸エステル類と単官能(メタ)アクリレート類との二種、又は、ビニルエーテル基含有(メタ)アクリル酸エステル類とウレタンポリ(メタ)アクリレート類との二種であることを特徴とする(メタ)アクリル酸エステル類。 (Meth) acrylic acid esters comprising an antioxidant,
The antioxidant has a phenyl group having at least a phenolic hydroxyl group,
The following general formula (1) has a structure in which a hydrogen atom is bonded to one of carbon atoms adjacent to the carbon atom to which the phenolic hydroxyl group is bonded, and an alkyl group is bonded to the other.
The (meth) acrylic acid esters, vinyl ether group-containing (meth) acrylic acid esters, multifunctional (meth) acrylates, second and vinyl ether group-containing (meth) acrylate and a monofunctional (meth) acrylates (Meth) acrylic acid ester characterized by being two kinds of seeds or vinyl ether group-containing (meth) acrylic acid esters and urethane poly (meth) acrylates .
前記多官能(メタ)アクリレート類は、トリメチロールプロパントリ(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、及び、グリセリントリ(メタ)アクリレートからなる群より選択される少なくとも1種の化合物であることを特徴とする請求項1又は2に記載の(メタ)アクリル酸エステル類。The polyfunctional (meth) acrylates are at least one compound selected from the group consisting of trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, and glycerin tri (meth) acrylate. The (meth) acrylic acid esters according to claim 1 or 2, wherein
該硬化方法は、該光硬化用組成物に紫外線を照射して硬化させることを特徴とする光硬化用組成物の硬化方法。 A method for curing the photocurable composition according to claim 6 , comprising:
The curing method is a method for curing a photocurable composition, wherein the photocurable composition is cured by irradiating with ultraviolet rays.
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