JP2019156973A - Manufacturing method of hardened material - Google Patents
Manufacturing method of hardened material Download PDFInfo
- Publication number
- JP2019156973A JP2019156973A JP2018045553A JP2018045553A JP2019156973A JP 2019156973 A JP2019156973 A JP 2019156973A JP 2018045553 A JP2018045553 A JP 2018045553A JP 2018045553 A JP2018045553 A JP 2018045553A JP 2019156973 A JP2019156973 A JP 2019156973A
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- JP
- Japan
- Prior art keywords
- meth
- vinyl
- acrylate
- acid
- ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 27
- 239000000463 material Substances 0.000 title abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 65
- 238000011156 evaluation Methods 0.000 claims abstract description 11
- 230000001678 irradiating effect Effects 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- -1 urethane acrylate compound Chemical class 0.000 claims description 275
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 171
- 150000001875 compounds Chemical class 0.000 claims description 123
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 17
- 238000001723 curing Methods 0.000 claims description 16
- 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 claims description 8
- 238000000016 photochemical curing Methods 0.000 claims description 3
- 208000035874 Excoriation Diseases 0.000 abstract 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 93
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 76
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 45
- 239000002253 acid Substances 0.000 description 43
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 37
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 30
- 229920002554 vinyl polymer Polymers 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- 239000000975 dye Substances 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 16
- 239000000049 pigment Substances 0.000 description 14
- 125000004122 cyclic group Chemical group 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000012860 organic pigment Substances 0.000 description 13
- 239000003999 initiator Substances 0.000 description 12
- 239000005056 polyisocyanate Substances 0.000 description 12
- 229920001228 polyisocyanate Polymers 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 150000003926 acrylamides Chemical class 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 9
- 229910000077 silane Inorganic materials 0.000 description 9
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 230000006872 improvement Effects 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 229960000834 vinyl ether Drugs 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 235000006708 antioxidants Nutrition 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 150000004985 diamines Chemical class 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 229940070710 valerate Drugs 0.000 description 7
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 6
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 6
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 5
- 229920002799 BoPET Polymers 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 150000004292 cyclic ethers Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 125000003566 oxetanyl group Chemical group 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 4
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- XHYCSVZWIGEZAS-UHFFFAOYSA-N 1-ethenyl-2h-quinoline Chemical compound C1=CC=C2N(C=C)CC=CC2=C1 XHYCSVZWIGEZAS-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- UJTRCPVECIHPBG-UHFFFAOYSA-N 3-cyclohexylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C2CCCCC2)=C1 UJTRCPVECIHPBG-UHFFFAOYSA-N 0.000 description 3
- YUCOVHFIYPJDDN-UHFFFAOYSA-N 4-prop-1-en-2-ylbenzoic acid Chemical compound CC(=C)C1=CC=C(C(O)=O)C=C1 YUCOVHFIYPJDDN-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229930016911 cinnamic acid Natural products 0.000 description 3
- 235000013985 cinnamic acid Nutrition 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- XMMDVXFQGOEOKH-UHFFFAOYSA-N n'-dodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCNCCCN XMMDVXFQGOEOKH-UHFFFAOYSA-N 0.000 description 3
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 3
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- 125000001302 tertiary amino group Chemical group 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
- GQLGFBRMCCVQLU-XCGJVMPOSA-N (6r)-7-amino-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C=C)=C(C(O)=O)N2C(=O)C(N)[C@H]21 GQLGFBRMCCVQLU-XCGJVMPOSA-N 0.000 description 2
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 2
- SNVRDQORMVVQBI-UPHRSURJSA-N (z)-but-2-enedihydrazide Chemical compound NNC(=O)\C=C/C(=O)NN SNVRDQORMVVQBI-UPHRSURJSA-N 0.000 description 2
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 2
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 2
- KBICSUODQLDGFE-UHFFFAOYSA-N 1-ethenylbenzimidazole Chemical compound C1=CC=C2N(C=C)C=NC2=C1 KBICSUODQLDGFE-UHFFFAOYSA-N 0.000 description 2
- PLWOURZNEOAFHE-UHFFFAOYSA-N 1-ethenylindazole Chemical compound C1=CC=C2N(C=C)N=CC2=C1 PLWOURZNEOAFHE-UHFFFAOYSA-N 0.000 description 2
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- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 2
- KHOUKKVJOPQVJM-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCC(CO)(CO)CO KHOUKKVJOPQVJM-UHFFFAOYSA-N 0.000 description 2
- FCMUPMSEVHVOSE-UHFFFAOYSA-N 2,3-bis(ethenyl)pyridine Chemical compound C=CC1=CC=CN=C1C=C FCMUPMSEVHVOSE-UHFFFAOYSA-N 0.000 description 2
- OJRJDENLRJHEJO-UHFFFAOYSA-N 2,4-diethylpentane-1,5-diol Chemical compound CCC(CO)CC(CC)CO OJRJDENLRJHEJO-UHFFFAOYSA-N 0.000 description 2
- 150000003923 2,5-pyrrolediones Chemical class 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
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- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
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- CIBGZAYGXFGOFK-UHFFFAOYSA-L zinc;2-phenylethenesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C=CC1=CC=CC=C1.[O-]S(=O)(=O)C=CC1=CC=CC=C1 CIBGZAYGXFGOFK-UHFFFAOYSA-L 0.000 description 1
Abstract
Description
本発明は、硬化物の製造方法に関する。 The present invention relates to a method for producing a cured product.
活性エネルギー線重合技術は、その速い重合速度、一般に無溶剤であることによる良好な作業性、省エネルギー化等の利点を有しているため、建装材料、包装材料、印刷材料、表示材料、電気電子部品材料、光学デバイス、ディスプレイなどの分野において、その利用分野は拡大傾向にある。 Active energy ray polymerization technology has advantages such as high polymerization speed, generally good workability due to the absence of solvent, and energy saving, so building materials, packaging materials, printing materials, display materials, electrical In the fields of electronic component materials, optical devices, displays, etc., their fields of use are expanding.
活性エネルギー線重合技術を用いた用途は多種多様であるが、例えば、ハードコートフィルムのハードコート層を製造する場合に使用されている。ハードコート層に適用される場合にはフィルムの薄膜化が要求される場合があり、その場合にフィルムの低カール性および良好なハードコート性を両立することが困難となる。例えば、特許文献1にそのようなカールの発生を低減させるためにコロイダルシリカ等の金属酸化物超微粒子を添加することが提案されているが、添加物が存在することによって、架橋密度が低下しハード特性が低下する問題があった。特許文献2に開示されている融点が125℃以上で粒径が0.1μm以下のワックス成分を含有させる方法では、耐擦傷性が向上すると考えられているが、添加物が存在することによって架橋密度が低下しハード特性が低下する問題があった。 There are a wide variety of uses using the active energy ray polymerization technique. For example, it is used for producing a hard coat layer of a hard coat film. When applied to a hard coat layer, it may be required to make the film thinner. In that case, it becomes difficult to achieve both low curl properties and good hard coat properties of the film. For example, in Patent Document 1, it is proposed to add metal oxide ultrafine particles such as colloidal silica in order to reduce the occurrence of such curling. However, the presence of the additive reduces the crosslinking density. There was a problem that the hard characteristics deteriorated. In the method of containing a wax component having a melting point of 125 ° C. or more and a particle size of 0.1 μm or less disclosed in Patent Document 2, it is considered that the scratch resistance is improved, but the presence of an additive causes crosslinking. There was a problem that the density was lowered and the hard characteristics were lowered.
本発明は、耐擦傷性や鉛筆硬度といったハードコート性に優れた硬化物を得ることが可能であり、優れた硬化速度を有する活性エネルギー線重合性組成物の硬化物を提供することを目的とする。 It is an object of the present invention to provide a cured product of an active energy ray-polymerizable composition having an excellent curing rate, which is capable of obtaining a cured product having excellent hard coat properties such as scratch resistance and pencil hardness. To do.
本発明は、活性エネルギー線重合性組成物に活性エネルギー線を照射して硬化物を形成する硬化物の製造方法であり、加熱処理によって活性エネルギー線重合性組成物を65℃以上とした状態で活性エネルギー線を照射することで、JIS K5600−5−4に基づく鉛筆硬度評価において5H以上の硬化度を発生させることを特徴とする硬化物の製造方法に関する。 This invention is a manufacturing method of the hardened | cured material which irradiates an active energy ray polymeric composition to an active energy ray, and forms hardened | cured material, In the state which made the active energy ray polymeric composition 65 degreeC or more by heat processing It is related with the manufacturing method of the hardened | cured material characterized by generating the hardening degree of 5H or more in pencil hardness evaluation based on JISK5600-5-4 by irradiating an active energy ray.
また、本発明は、活性エネルギー線重合性組成物が光ラジカル硬化系であることを特徴とする前記硬化物の製造方法に関する。 Moreover, this invention relates to the manufacturing method of the said hardened | cured material characterized by the active energy ray polymeric composition being a radical photocuring type | system | group.
また、本発明は、活性エネルギー線重合性組成物全量中、分子内に(メタ)アクリロイル基を4個以上含有する化合物(A)を50〜100質量%含有することを特徴とする前記硬化物の製造方法に関する。 Moreover, this invention contains 50-100 mass% of compounds (A) which contain 4 or more of (meth) acryloyl groups in a molecule | numerator in the active energy ray polymeric composition whole quantity, The said hardened | cured material characterized by the above-mentioned. It relates to the manufacturing method.
また、本発明は、分子内に(メタ)アクリロイル基を4個以上含有する化合物(A)がウレタンアクリレート化合物(a1)であることを特徴とする前記硬化物の製造方法に関する。 Moreover, this invention relates to the manufacturing method of the said hardened | cured material characterized by the compound (A) containing four or more (meth) acryloyl groups in a molecule | numerator being a urethane acrylate compound (a1).
また、本発明は、分子内に(メタ)アクリロイル基を4個以上含有する化合物(A)がウレタンアクリレート化合物(a1)、およびジペンタエリスリトールヘキサ(メタ)アクリレートであることを特徴とする前記硬化物の製造方法に関する。 The present invention is also characterized in that the compound (A) containing four or more (meth) acryloyl groups in the molecule is a urethane acrylate compound (a1) and dipentaerythritol hexa (meth) acrylate. The present invention relates to a method for manufacturing a product.
本発明により、耐擦傷性や鉛筆硬度といったハードコート性に優れた硬化物を得ることが可能であり、優れた硬化速度を有する活性エネルギー線重合性組成物の硬化物を提供することができるようになった。 According to the present invention, a cured product excellent in hard coat properties such as scratch resistance and pencil hardness can be obtained, and a cured product of an active energy ray polymerizable composition having an excellent curing rate can be provided. Became.
以下、本発明の実施形態について説明する。
なお、本明細書では、「(メタ)アクリロイル」、「(メタ)アクリル酸」、「(メタ)アクリレート」、及び「(メタ)アクリロイルオキシ」とは、特に説明がない限り、それぞれ、「アクリロイル及び/又はメタクリロイル」、「アクリル酸及び/又はメタクリル酸」、「アクリレート及び/又はメタクリレート」、並びに「アクリロイルオキシ及び/又はメタクリロイルオキシ」を表すものとする。また、「活性エネルギー線重合性組成物」は「重合性組成物」と略記することがある。
Hereinafter, embodiments of the present invention will be described.
In the present specification, “(meth) acryloyl”, “(meth) acrylic acid”, “(meth) acrylate”, and “(meth) acryloyloxy” are “acryloyl” unless otherwise specified. And / or “methacryloyl”, “acrylic acid and / or methacrylic acid”, “acrylate and / or methacrylate”, and “acryloyloxy and / or methacryloyloxy”. Further, the “active energy ray polymerizable composition” may be abbreviated as “polymerizable composition”.
本発明は、活性エネルギー線重合性組成物を65℃以上にすることで、活性エネルギー線重合性組成物中に含まれる分子の運動を活発化させた状態で活性エネルギー線を照射し、活性エネルギー線重合性組成物中の反応性化合物の反応をより促進させることを特徴とした耐擦傷性や鉛筆硬度といったハードコート性に優れた硬化物の製造方法に関するものである。 In the present invention, the active energy ray-polymerizable composition is heated to 65 ° C. or higher to irradiate active energy rays in a state in which the movement of molecules contained in the active energy ray-polymerizable composition is activated. The present invention relates to a method for producing a cured product excellent in hard coat properties such as scratch resistance and pencil hardness, which is characterized by further promoting the reaction of a reactive compound in a linear polymerizable composition.
ここで、「活性エネルギー線」とは、紫外線、可視光線、赤外線、電子線、及び放射線を含む、化学反応を生じさせるための活性化に必要なエネルギーを提供できる、広義のエネルギー線を意味する。特に限定するものではないが、本発明の一実施形態において、上記活性エネルギー線は、紫外線を含む光エネルギー線であることが好ましい。 Here, the “active energy ray” means an energy ray in a broad sense that can provide energy necessary for activation for causing a chemical reaction, including ultraviolet rays, visible rays, infrared rays, electron beams, and radiation. . Although it does not specifically limit, In one Embodiment of this invention, it is preferable that the said active energy ray is a light energy ray containing an ultraviolet-ray.
本発明の硬化物の製造法は、活性エネルギー線重合性組成物をロールコーター、スピンコーター、グラビアコーター、コンマコーター、バーコーター、カーテンコーター、ダイコーター、インクジェットプリンターなどを用いてシート状基材上に塗布し、これを65℃以上となるよう加熱した状態にて、活性エネルギー線を照射する事で、硬化物を形成することができる。シート状基材として、本発明で用いられるものに制限はないが、紙、不織布、布地、多孔質ガラスシートなどの多孔質性基材、あるいは合成紙、コート紙、高分子フィルム、金属箔などの基材等を使用することが可能である。 The method for producing a cured product according to the present invention is a method in which an active energy ray polymerizable composition is applied on a sheet-like substrate using a roll coater, a spin coater, a gravure coater, a comma coater, a bar coater, a curtain coater, a die coater, an inkjet printer, or the like. A cured product can be formed by irradiating with active energy rays in a state of being heated to 65 ° C. or higher. Although there is no restriction | limiting in what is used by this invention as a sheet-like base material, Porous base materials, such as paper, a nonwoven fabric, a fabric, a porous glass sheet, or synthetic paper, a coated paper, a polymer film, metal foil, etc. It is possible to use a base material or the like.
加熱処理は活性エネルギー線照射直前から照射時に実施する事が好ましく、オーブンやシートヒーター等が使用可能である。活性エネルギー線照射直前の活性エネルギー線重合性組成物の温度範囲は、65℃以上であり、65℃〜100℃の範囲が好ましい。さらには耐擦傷性の観点から、75〜90℃の範囲がより好ましい。65℃未満であると活性エネルギー線重合性組成物中に含まれる分子の運動を活発化が十分ではなく、100℃を超えると活性エネルギー線重合性組成物の流動性が向上し過ぎたり、一部活性エネルギー線照射前に硬化が進行したりすることで、作業性の低下に繋がる。 The heat treatment is preferably performed immediately before the irradiation with active energy rays, and an oven or a sheet heater can be used. The temperature range of the active energy ray polymerizable composition immediately before irradiation with the active energy ray is 65 ° C. or higher, and a range of 65 ° C. to 100 ° C. is preferable. Furthermore, the range of 75-90 degreeC is more preferable from a viewpoint of abrasion resistance. If the temperature is less than 65 ° C., the movement of the molecules contained in the active energy ray polymerizable composition is not sufficiently activated. If the temperature exceeds 100 ° C., the fluidity of the active energy ray polymerizable composition is excessively improved. Curing progresses before partial active energy ray irradiation, leading to a decrease in workability.
本発明の硬化物の製造法により、容易に耐擦傷性に優れ、鉛筆硬度にて5H以上の硬化物を作製する事が可能となる。 According to the method for producing a cured product of the present invention, it is possible to easily produce a cured product having excellent scratch resistance and having a pencil hardness of 5H or more.
本発明の重合性組成物は、粘度の制限はなく、粘度または求める塗布後の膜厚に併せた塗工方法を上記記載の方法から選択する。また、粘度の調整が必要となる場合は、実質的に有機溶剤を含まないことが好ましいが、有機溶剤を含有することも可能である。例えば、メタノール、エタノール、イソプロピルアルコール、アセトン、メチルエチルケトン、メチルイソブチルケトン、酢酸メチル、酢酸エチル、酢酸ブチル、シクロヘキサン、トルエン、キシレンその他の炭化水素系溶媒等の有機溶剤や、水をさらに添加して、重合性組成物の粘度を調整することもできる。有機溶剤や水を添加した場合、活性エネルギー線を照射する前に乾燥工程を入れる事が好ましい。 The polymerizable composition of the present invention is not limited in viscosity, and a coating method according to the viscosity or a desired film thickness after coating is selected from the methods described above. Moreover, when it is necessary to adjust the viscosity, it is preferable that the organic solvent is not substantially contained, but an organic solvent can also be contained. For example, further adding organic solvents such as methanol, ethanol, isopropyl alcohol, acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl acetate, ethyl acetate, butyl acetate, cyclohexane, toluene, xylene and other hydrocarbon solvents, water, The viscosity of the polymerizable composition can also be adjusted. When an organic solvent or water is added, it is preferable to put a drying step before irradiation with active energy rays.
以下、本発明における活性エネルギー線重合性組成物を構成する各成分について詳述する。 Hereinafter, each component which comprises the active energy ray polymeric composition in this invention is explained in full detail.
<分子内に(メタ)アクリロイル基を4個以上含有する化合物(A)>
本発明において、分子内に(メタ)アクリロイル基を4個以上含有する化合物(A)(以下「化合物(A)」と略記することがある)は、分子内に(メタ)アクリロイル基を4個以上含有する化合物の総称である。
<Compound (A) containing 4 or more (meth) acryloyl groups in the molecule>
In the present invention, the compound (A) containing 4 or more (meth) acryloyl groups in the molecule (hereinafter sometimes abbreviated as “compound (A)”) has 4 (meth) acryloyl groups in the molecule. It is a general term for the compounds contained above.
化合物(A)としては、分子内に(メタ)アクリロイル基を4個以上含有する化合物であれば、特に制限はなく使用できる。化合物(A)の例としては、ペンタエリスリトールテトラ(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、ジペンタエリスリトールペンタ(メタ)アクリレートモノプロピオネート、ジペンタエリスリトールヘキサ(メタ)アクリレート、テトラメチロールメタンテトラ(メタ)アクリレート、オリゴエステルテトラ(メタ)アクリレート等が挙げられるが、特にこれらに限定されるものではない。これらは1種だけを用いてもよいし、あるいは複数種を併用してもよい。 The compound (A) is not particularly limited as long as it is a compound containing 4 or more (meth) acryloyl groups in the molecule. Examples of the compound (A) include pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate monopropionate, dipentaerythritol hexa (meth) acrylate, tetramethylol. Examples include methanetetra (meth) acrylate and oligoestertetra (meth) acrylate, but are not particularly limited thereto. These may use only 1 type or may use multiple types together.
特に限定するものではないが、本発明の好ましい一実施形態において、化合物(A)は、下記記載のウレタンアクリレート化合物(a1)であることが好ましく、下記記載のウレタンアクリレート化合物(a1)、およびジペンタエリスリトールヘキサ(メタ)アクリレートであることがさらに好ましい。ジペンタエリスリトールヘキサ(メタ)アクリレートは、容易に入手可能でありかつ、安価であることが好ましく、下記記載のウレタンアクリレート化合物(a1)は、耐擦傷性や鉛筆硬度といったハードコート性に加えて、ウレタン結合に基づいた柔軟性を付与することも可能となり、硬くてしなやかな硬化物を提供する事が可能となる。更に、耐加水分解性も良好な為に、耐水性や耐湿熱性を容易に向上させることも可能となる。 Although not particularly limited, in one preferred embodiment of the present invention, the compound (A) is preferably the urethane acrylate compound (a1) described below, the urethane acrylate compound (a1) described below, and di More preferably, it is pentaerythritol hexa (meth) acrylate. Dipentaerythritol hexa (meth) acrylate is preferably easily available and inexpensive, and the urethane acrylate compound (a1) described below has hard coat properties such as scratch resistance and pencil hardness, Flexibility based on the urethane bond can be imparted, and a hard and supple cured product can be provided. Furthermore, since the hydrolysis resistance is also good, it becomes possible to easily improve the water resistance and heat-and-moisture resistance.
<ウレタンアクリレート化合物(a1)>
本発明において、ウレタンアクリレート化合物(a1)(以下「化合物(a1)」と略記することがある)は、少なくとも1個以上のイソシアネート基を有する化合物と、分子内に1個以上の水酸基を有する(メタ)アクリロイル基含有化合物とを反応させて得られる化合物、あるいは少なくとも1個のイソシアネート基を有する化合物と多価アルコールとを反応させて得られる末端イソシアネート基のウレタンプレポリマーと、分子内に1個以上の水酸基を有する(メタ)アクリロイル基含有化合物とを反応させて得られる化合物、あるいは少なくとも1個のイソシアネート基を有する化合物と多価アルコールとを反応させて得られる末端イソシアネート基のウレタンプレポリマーと、更に少なくとも1個以上のアミノ基を有する化合物とを反応させて得られる末端イソシアネート基のウレタンプレポリマーと、分子内に1個以上の水酸基を有する(メタ)アクリロイル基含有化合物とを反応させて得られる化合物である。また、イソシアネート基とアミノ基とを反応させて得られるウレア結合基を含有したものも化合物(a1)に含む。
本発明に用いるウレタンアクリレート化合物(a1)は、上記説明の中から(メタ)アクリロイル基を4個以上含有するように反応させた化合物を選択したものである。
<Urethane acrylate compound (a1)>
In the present invention, the urethane acrylate compound (a1) (hereinafter sometimes abbreviated as “compound (a1)”) has a compound having at least one isocyanate group and one or more hydroxyl groups in the molecule ( A compound obtained by reacting a (meth) acryloyl group-containing compound, or a urethane prepolymer having a terminal isocyanate group obtained by reacting a compound having at least one isocyanate group with a polyhydric alcohol, and one in the molecule A compound obtained by reacting the (meth) acryloyl group-containing compound having the above hydroxyl group or a urethane prepolymer having a terminal isocyanate group obtained by reacting a compound having at least one isocyanate group with a polyhydric alcohol; And a compound having at least one amino group; A urethane prepolymer terminal isocyanate groups obtained by reacting a compound obtained by reacting with one or more hydroxyl groups (meth) acryloyl group-containing compound in the molecule. Further, the compound (a1) includes a compound containing a urea bond group obtained by reacting an isocyanate group with an amino group.
The urethane acrylate compound (a1) used in the present invention is a compound selected from the above description so as to contain 4 or more (meth) acryloyl groups.
少なくとも1個のイソシアネート基を有する化合物としては、単官能ポリイソシアネート、及び多官能イソシアネートが挙げられ、それぞれ、芳香族ポリイソシアネート、脂肪族ポリイソシアネート、芳香脂肪族ポリイソシアネート、脂環族ポリイソシアネート等が挙げられる。単官能ポリイソシアネートとしては、より具体的に、例えば、メチルイソシアネート、エチルイソシアネート、プロピルイソシアネート、ブチルイソシアネート、オクチルイソシアネート、デシルイソシアネート、オクタデシルイソシアネート、ステアリルイソシアネート、シクロヘキシルイソシアネート、フェニルイソシアネート、ベンジルイソシアネート、p−クロロフェニルイソシアネート、p−ニトロフェニルイソシアネート、2−クロロエチルイソシアネート、2,4−ジクロロフェニルイソシアネート、3−クロロ−4−メチルフェニルイソシアネート、トリクロロアセチルイソシアネート、クロロスルホニルイソシアネート、(R)−(+)−α−メチルベンジルイソシアネート、(S)−(−)−α−メチルベンジルイソシアネート、(R)−(−)−1−(1−ナフチル)エチルイソシアネート、(R)−(+)−1−フェニルエチルイソシアネート、(S)−(−)−1−フェニルエチルイソシアネート、p−トルエンスルホニルイソシアネート等が挙げられる。 Examples of the compound having at least one isocyanate group include monofunctional polyisocyanates and polyfunctional isocyanates, and aromatic polyisocyanates, aliphatic polyisocyanates, araliphatic polyisocyanates, alicyclic polyisocyanates, etc., respectively. Can be mentioned. More specifically, as monofunctional polyisocyanate, for example, methyl isocyanate, ethyl isocyanate, propyl isocyanate, butyl isocyanate, octyl isocyanate, decyl isocyanate, octadecyl isocyanate, stearyl isocyanate, cyclohexyl isocyanate, phenyl isocyanate, benzyl isocyanate, p-chlorophenyl Isocyanate, p-nitrophenyl isocyanate, 2-chloroethyl isocyanate, 2,4-dichlorophenyl isocyanate, 3-chloro-4-methylphenyl isocyanate, trichloroacetyl isocyanate, chlorosulfonyl isocyanate, (R)-(+)-α-methyl Benzyl isocyanate, (S)-(−)-α-methylbenzyl isocyanate, (R )-(−)-1- (1-naphthyl) ethyl isocyanate, (R)-(+)-1-phenylethyl isocyanate, (S)-(−)-1-phenylethyl isocyanate, p-toluenesulfonyl isocyanate, etc. Is mentioned.
多官能イソシアネートのうち、芳香族ポリイソシアネートとしては、より具体的に、例えば、1,3−フェニレンジイソシアネート、4,4’−ジフェニルジイソシアネート、1,4−フェニ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(別名:4,4’−MDI)、2,4−トリレンジイソシアネート(別名:2,4−TDI)、2,6−トリレンジイソシアネート、4,4’−トルイジンジイソシアネート、2,4,6−トリイソシアネートトルエン、1,3,5−トリイソシアネートベンゼン、ジアニシジンジイソシアネート、4,4’−ジフェニルエーテルジイソシアネート、4,4’,4”−トリフェニルメタントリイソシアネート等を挙げることができる。 Among the polyfunctional isocyanates, the aromatic polyisocyanate is more specifically, for example, 1,3-phenylene diisocyanate, 4,4′-diphenyl diisocyanate, 1,4-phenylene diisocyanate, 4,4′-diphenylmethane diisocyanate ( Alias: 4,4′-MDI), 2,4-tolylene diisocyanate (alias: 2,4-TDI), 2,6-tolylene diisocyanate, 4,4′-toluidine diisocyanate, 2,4,6-tri Examples include isocyanate toluene, 1,3,5-triisocyanate benzene, dianisidine diisocyanate, 4,4′-diphenyl ether diisocyanate, 4,4 ′, 4 ″ -triphenylmethane triisocyanate, and the like.
脂肪族ポリイソシアネートとしては、トリメチレンジイソシアネート、テトラメチレンジイソシアネート、ヘキサメチレンジイソシアネート(別名:HDI)、ペンタメチレンジイソシアネート、1,2−プロピレンジイソシアネート、2,3−ブチレンジイソシアネート、1,3−ブチレンジイソシアネート、ドデカ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等を挙げることができる。 Aliphatic polyisocyanates include trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate (also known as HDI), pentamethylene diisocyanate, 1,2-propylene diisocyanate, 2,3-butylene diisocyanate, 1,3-butylene diisocyanate, dodeca Examples include methylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate.
芳香脂肪族ポリイソシアネートとしては、ω,ω’−ジイソシアネート−1,3−ジメチルベンゼン、ω,ω’−ジイソシアネート−1,4−ジメチルベンゼン、ω,ω’−ジイソシアネート−1,4−ジエチルベンゼン、1,4−テトラメチルキシリレンジイソシアネート、1,3−テトラメチルキシリレンジイソシアネート等を挙げることができる。 Examples of the araliphatic polyisocyanate include ω, ω′-diisocyanate-1,3-dimethylbenzene, ω, ω′-diisocyanate-1,4-dimethylbenzene, ω, ω′-diisocyanate-1,4-diethylbenzene, , 4-tetramethylxylylene diisocyanate, 1,3-tetramethylxylylene diisocyanate, and the like.
脂環族ポリイソシアネートとしては、3−イソシアネートメチル−3,5,5−トリメチルシクロヘキシルイソシアネート(別名:IPDI)、1,3−シクロペンタンジイソシアネート、1,3−シクロヘキサンジイソシアネート、1,4−シクロヘキサンジイソシアネート、メチル−2,4−シクロヘキサンジイソシアネート、メチル−2,6−シクロヘキサンジイソシアネート、4,4’−メチレンビス(シクロヘキシルイソシアネート)、1,4−ビス(イソシアネートメチル)シクロヘキサン等を挙げることができる。 As the alicyclic polyisocyanate, 3-isocyanate methyl-3,5,5-trimethylcyclohexyl isocyanate (also known as IPDI), 1,3-cyclopentane diisocyanate, 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, Examples thereof include methyl-2,4-cyclohexane diisocyanate, methyl-2,6-cyclohexane diisocyanate, 4,4′-methylenebis (cyclohexyl isocyanate), 1,4-bis (isocyanatomethyl) cyclohexane and the like.
また、化合物(a1)成分の一部として、上記、ポリイソシアネートの2−メチルペンタン−2,4−ジオールアダクト体、イソシアヌレート環を有する3量体等も併用することができる。ポリフェニルメタンポリイソシアネート(別名:PAPI)、ナフチレンジイソシアネート、及びこれらのポリイソシアネート変性物等を使用し得る。なおポリイソシアネート変性物としては、カルボジイミド基、ウレトジオン基、ウレトンイミン基、水と反応したビュレット基、イソシアヌレート基のいずれかの基、又はこれらの基の2種以上を有する変性物を使用できる。ポリオールとジイソシアネートの反応物も少なくとも2個のイソシアネート基を有する化合物として使用することができる。
また、アミノ基を有するアミン類としては、、例えばアミノメタン、アミノエタン、1−アミノプロパン、2−アミノプロパン、1−アミノブタン、2−アミノブタン、1−アミノペンタン、2−アミノペンタン、3−アミノペンタン、イソアミルアミン、1−アミノヘキサン、1−アミノヘプタン、2−アミノヘプタン、2−オクチルアミン、1−アミノノナン、1−アミノデカン、1−アミノドデカン(ラウリルアミン)、1−アミノトリデカン、1−アミノヘキサデカン、1−アミノテトラデデカン(ミリスチルアミン)、1−アミノペンタデカン、セチルアミン、オレイルアミン、ココアルキルアミン、牛脂アルキルアミン、硬化牛脂アルキルアミン、アリルアミン、ステアリルアミン、アミノシクロプロパン、アミノシクロブタン、アミノシクロペンタン、アミノシクロヘキサン、アミノシクロドデカン、1−アミノ−2−エチルヘキサン、1−アミノ−2−メチルプロパン、2−アミノ−2−メチルプロパン、3−アミノ−1−プロペン、3−アミノメチルヘプタン、3−イソプロポキシプロピルアミン、3−ブトキシプロピルアミン、3−イソブトキシプロピルアミン、2−エチルヘキシロキシプロピルアミン、3−デシロキシプロピルアミン、3−ラウリロキシプロピルアミン、3−ミリスチロキシプロピルアミン、2−アミノメチルテトラヒドロフラン、アニリン、o−アミノトルエン、m−アミノトルエン、p−アミノトルエン、o−ベンジルアニリン、p−ベンジルアニリン、1−アニリノナフタレン、1−アミノアントラキノン、2−アミノアントラキノン、1−アミノアントラセン、2−アミノアントラセン、5−アミノイソキノリン、o−アミノジフェニル、4−アミノジフェニルエーテル、2−アミノベンゾフェノン、4−アミノベンゾフェノン、o−アミノアセトフェノン、m−アミノアセトフェノン、p−アミノアセトフェノン、ベンジルアミン、α−フェニルエチルアミン、フェネシルアミン、p−メトキシフェネシルアミン、p−アミノアゾベンゼン、m−アミノフェノール、p−アミノフェノール、アリルアミン等の1級アミン類;
In addition, as a part of the compound (a1) component, the above-described 2-methylpentane-2,4-diol adduct of polyisocyanate, trimer having an isocyanurate ring, and the like can be used in combination. Polyphenylmethane polyisocyanate (also known as PAPI), naphthylene diisocyanate, and polyisocyanate-modified products thereof can be used. As the polyisocyanate-modified product, a carbodiimide group, a uretdione group, a uretonimine group, a burette group reacted with water, a group of isocyanurate groups, or a modified product having two or more of these groups can be used. A reaction product of a polyol and a diisocyanate can also be used as a compound having at least two isocyanate groups.
Examples of amines having an amino group include aminomethane, aminoethane, 1-aminopropane, 2-aminopropane, 1-aminobutane, 2-aminobutane, 1-aminopentane, 2-aminopentane, and 3-aminopentane. , Isoamylamine, 1-aminohexane, 1-aminoheptane, 2-aminoheptane, 2-octylamine, 1-aminononane, 1-aminodecane, 1-aminododecane (laurylamine), 1-aminotridecane, 1-amino Hexadecane, 1-aminotetradecane (myristylamine), 1-aminopentadecane, cetylamine, oleylamine, cocoalkylamine, beef tallow alkylamine, cured tallow alkylamine, allylamine, stearylamine, aminocyclopropane, aminocyclobutane, amino Nocyclopentane, aminocyclohexane, aminocyclododecane, 1-amino-2-ethylhexane, 1-amino-2-methylpropane, 2-amino-2-methylpropane, 3-amino-1-propene, 3-aminomethyl Heptane, 3-isopropoxypropylamine, 3-butoxypropylamine, 3-isobutoxypropylamine, 2-ethylhexyloxypropylamine, 3-decyloxypropylamine, 3-lauryloxypropylamine, 3-myristoxypropyl Amine, 2-aminomethyltetrahydrofuran, aniline, o-aminotoluene, m-aminotoluene, p-aminotoluene, o-benzylaniline, p-benzylaniline, 1-anilinonanaphthalene, 1-aminoanthraquinone, 2-aminoanthraquinone 1 Aminoanthracene, 2-aminoanthracene, 5-aminoisoquinoline, o-aminodiphenyl, 4-aminodiphenyl ether, 2-aminobenzophenone, 4-aminobenzophenone, o-aminoacetophenone, m-aminoacetophenone, p-aminoacetophenone, benzylamine Primary amines such as α-phenylethylamine, phenesylamine, p-methoxyphenesylamine, p-aminoazobenzene, m-aminophenol, p-aminophenol, allylamine;
例えば、ジメチルアミン、ジエチルアミン、N−メチルエチルアミン、N−メチルイソプロピルアミン、N−メチルヘキシルアミン、ジイソプロピルアミン、ジn−プロピルアミン、ジn−ブチルアミン、ジsec−ブチルアミン、N−エチル−1,2−ジメチルプロピルアミン、ピペリジン、2−ピペコリン、3−ピペコリン、4−ピペコリン、2,4−ルペチジン、2,6−ルペチジン、3,5−ルペチジン、3−ピペリジンメタノール、2−ピペリジンエタノール、4−ピペリジンエタノール、4−ピペリジノール、ピロリジン、3−アミノピロリジン、、3−ピロリジノール、ジアミルアミン、ジアリルアミン、メチルアニリン、エチルアニリン、ジベンジルアミン、ジフェニルアミン、ジココアルキルアミン、ジ硬化牛脂アルキルアミン、ジステアリルアミン等の2級アミン類; For example, dimethylamine, diethylamine, N-methylethylamine, N-methylisopropylamine, N-methylhexylamine, diisopropylamine, di-n-propylamine, di-n-butylamine, disec-butylamine, N-ethyl-1,2 -Dimethylpropylamine, Piperidine, 2-Pipecoline, 3-Pipecoline, 4-Pipecoline, 2,4-Lupetidine, 2,6-Lupetidine, 3,5-Lupetidine, 3-piperidinemethanol, 2-piperidineethanol, 4-piperidine Ethanol, 4-piperidinol, pyrrolidine, 3-aminopyrrolidine, 3-pyrrolidinol, diamylamine, diallylamine, methylaniline, ethylaniline, dibenzylamine, diphenylamine, dicocoalkylamine, di-cured tallow alkyl Min, secondary amines such as di-stearylamine;
例えば、エチレンジアミン、プロピレンジアミン[別名:1,2−ジアミノプロパン又は1,2−プロパンジアミン]、トリメチレンジアミン[別名:1,3−ジアミノプロパン又は1,3−プロパンジアミン]、テトラメチレンジアミン[別名:1,4−ジアミノブタン]、2−メチル−1,3−プロパンジアミン、ペンタメチレンジアミン[別名:1,5−ジアミノペンタン]、ヘキサメチレンジアミン[別名:1,6−ジアミノヘキサン]、ジエチレントリアミン、トリアミノプロパン、2,2−ジメチル−1,3−プロパンジアミン、2,2,4−トリメチルヘキサメチレンジアミン、イソホロンジアミン、ダイマージアミン、ジシクロヘキシルメタン−4,4'−ジアミン、ジエチレングリコールビス(3−アミノプロピル)エーテル、フェニレンジアミン、、キシリレンジアミン、ジシクロヘキシルメタン−4,4’−ジアミン、2,4−トリレンジアミン、2,6−トリレンジアミン、ジエチルトルエンジアミン,3,3’−ジクロロ−4,4’−ジアミノジフェニルメタン、4,4’−ビス−(sec−ブチル)ジフェニルメタン、グルタミン、アスパラギン、リジン、ジアミノプロピオン酸、オルニチン、ジアミノ安息香酸、ジアミノベンゼンスルホン酸等二つの1級アミノ基有するジアミン類; For example, ethylenediamine, propylenediamine [alias: 1,2-diaminopropane or 1,2-propanediamine], trimethylenediamine [alias: 1,3-diaminopropane or 1,3-propanediamine], tetramethylenediamine [alias : 1,4-diaminobutane], 2-methyl-1,3-propanediamine, pentamethylenediamine [alias: 1,5-diaminopentane], hexamethylenediamine [alias: 1,6-diaminohexane], diethylenetriamine, Triaminopropane, 2,2-dimethyl-1,3-propanediamine, 2,2,4-trimethylhexamethylenediamine, isophoronediamine, dimer diamine, dicyclohexylmethane-4,4′-diamine, diethylene glycol bis (3-amino Propyl) ether Phenylenediamine, xylylenediamine, dicyclohexylmethane-4,4′-diamine, 2,4-tolylenediamine, 2,6-tolylenediamine, diethyltoluenediamine, 3,3′-dichloro-4,4′- Diamines having two primary amino groups such as diaminodiphenylmethane, 4,4′-bis- (sec-butyl) diphenylmethane, glutamine, asparagine, lysine, diaminopropionic acid, ornithine, diaminobenzoic acid, diaminobenzenesulfonic acid;
例えば、N,N−ジメチルエチレンジアミン、N,N−ジエチルエチレンジアミン、及びN,N'−ジ−tert−ブチルエチレンジアミン、ピペラジン等の二つの2級アミノ基有するジアミン類; For example, diamines having two secondary amino groups such as N, N-dimethylethylenediamine, N, N-diethylethylenediamine, and N, N′-di-tert-butylethylenediamine, piperazine;
例えば、N−メチルエチレンジアミン[別名:メチルアミノエチルアミン]、N−エチルエチレンジアミン[別名:エチルアミノエチルアミン]、N−メチル−1,3−プロパンジアミン[別名:N−メチル−1,3−ジアミノプロパン又はメチルアミノプロピルアミン]、N,2−メチル−1,3−プロパンジアミン、N−イソプロピルエチレンジアミン[別名:イソプロピルアミノエチルアミン]、N−イソプロピル−1,3−ジアミノプロパン[別名:N−イソプロピル−1,3−プロパンジアミン又はイソプロピルアミノプロピルアミン]、及びN−ラウリル−1,3−プロパンジアミン[別名:N−ラウリル−1,3−ジアミノプロパン又はラウリルアミノプロピルアミン]、トリエチルテトラミン、ジエチレントリアミン、2−ヒドロキシエチルエチレンジアミン、ヘキサメチレンジアミン2−ヒドロキシエチルエチレンジアミン、N−(2−ヒドロキシエチル)プロピレンジアミン、(2−ヒドロキシエチルプロピレン)ジアミン、(ジ−2−ヒドロキシエチルエチレン)ジアミン、(ジ−2−ヒドロキシエチルプロピレン)ジアミン、(2−ヒドロキシプロピルエチレン)ジアミン、(ジ−2−ヒドロキシプロピルエチレン)ジアミン等の1級及び2級アミノ基を有するポリアミン類; For example, N-methylethylenediamine [alias: methylaminoethylamine], N-ethylethylenediamine [alias: ethylaminoethylamine], N-methyl-1,3-propanediamine [alias: N-methyl-1,3-diaminopropane or Methylaminopropylamine], N, 2-methyl-1,3-propanediamine, N-isopropylethylenediamine [alias: isopropylaminoethylamine], N-isopropyl-1,3-diaminopropane [alias: N-isopropyl-1, 3-propanediamine or isopropylaminopropylamine], and N-lauryl-1,3-propanediamine [alias: N-lauryl-1,3-diaminopropane or laurylaminopropylamine], triethyltetramine, diethylenetriamine, 2- Droxyethylethylenediamine, hexamethylenediamine 2-hydroxyethylethylenediamine, N- (2-hydroxyethyl) propylenediamine, (2-hydroxyethylpropylene) diamine, (di-2-hydroxyethylethylene) diamine, (di-2- Polyamines having primary and secondary amino groups, such as hydroxyethylpropylene) diamine, (2-hydroxypropylethylene) diamine, (di-2-hydroxypropylethylene) diamine;
例えば、シュウ酸ジヒドラジド、マロン酸ジヒドラジド、コハク酸ジヒドラジド、グルタル酸ジヒドラジド、アジピン酸ジヒドラジド、セバシン酸ジヒドラジド、ドデカン二酸ジヒドラジド、ヘキサデカンジオヒドラジド、エイコサン二酸ジヒドラジド、マレイン酸ジヒドラジド、フマル酸ジヒドラジド、イタコン酸ジヒドラジド、フタル酸ジヒドラジド、炭酸ジヒドラジド、カルボジヒドラジド、チオカルボジヒドラジド、オキサリルジヒドラジド、ポリアクリル酸ヒドラジド等のヒドラジド類; For example, oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, sebacic acid dihydrazide, dodecanedioic acid dihydrazide, hexadecanediohydrazide, eicosanedioic acid dihydrazide, maleic acid dihydrazide acid, maleic acid dihydrazide acid, Hydrazides such as dihydrazide, phthalic acid dihydrazide, carbonic acid dihydrazide, carbodihydrazide, thiocarbodihydrazide, oxalyl dihydrazide, polyacrylic acid hydrazide;
例えば、トリメチルアミン、トリエチルアミン、トリプロピルアミン、トリブチルアミン、トリアミルアミン、ジメチルアニリン、ジエチルアニリン、トリベンジルアミン、N,N−ジメチルベンジルアミン、N−メチルモルホリン、ジアザビシクロウンデセン(別名:DBU)、1,5−ジアザビシクロ−[4.3.0]−5−ノネン等の3級アミン類; For example, trimethylamine, triethylamine, tripropylamine, tributylamine, triamylamine, dimethylaniline, diethylaniline, tribenzylamine, N, N-dimethylbenzylamine, N-methylmorpholine, diazabicycloundecene (also known as DBU) , Tertiary amines such as 1,5-diazabicyclo- [4.3.0] -5-nonene;
例えば、その他、ピリジン、モルホリン、N−メチルモルホリン、ピロリジン、ピペリジン、N−メチルピペリジン、ジメチルオキサゾリン、イミダゾール、N−メチルイミダゾール、N,N−ジメチルエタノールアミン、N,N−ジエチルエタノールアミン、N,N−ジメチルイソプロパノールアミン、N−メチルジエタノールアミン等を使用することができる。 For example, pyridine, morpholine, N-methylmorpholine, pyrrolidine, piperidine, N-methylpiperidine, dimethyloxazoline, imidazole, N-methylimidazole, N, N-dimethylethanolamine, N, N-diethylethanolamine, N, N-dimethylisopropanolamine, N-methyldiethanolamine and the like can be used.
<ラジカル重合性化合物(B)>
本発明の重合性組成物の一実施形態において、重合性組成物は、ラジカル重合性化合物(B) (以下「化合物(B)」と略記することがある)を含んでもよい。化合物(B)を使用することによって、重合性組成物の粘度を調整する事で作業性を向上したり、所定の硬度発現に繋がる反応率向上が期待できる。
<Radically polymerizable compound (B)>
In one embodiment of the polymerizable composition of the present invention, the polymerizable composition may contain a radical polymerizable compound (B) (hereinafter sometimes abbreviated as “compound (B)”). By using the compound (B), workability can be improved by adjusting the viscosity of the polymerizable composition, and an improvement in reaction rate that leads to a predetermined hardness can be expected.
特に、1個以上のα,β−不飽和二重結合基を含有する化合物であれば、特に制限はなく使用できるが、その構造中に1個以上の水酸基を含有するα,β−エチレン性不飽和二重結合基含有化合物(b1)を含有することが反応速度の向上や重合硬化収縮の抑制の点で好ましい。化合物(b1)には、水酸基を有し、環状構造を有しない化合物(b1−1)と、水酸基を有し、環状構造を有する化合物(b1−2)に分けられるが、いずれも水酸基を有することによって、重合反応に伴う硬化収縮の低減に大きな効果を示す。 In particular, any compound containing one or more α, β-unsaturated double bond groups can be used without any limitation, but α, β-ethylenic compounds containing one or more hydroxyl groups in the structure thereof can be used. It is preferable to contain the unsaturated double bond group-containing compound (b1) from the viewpoint of improving the reaction rate and suppressing polymerization curing shrinkage. The compound (b1) is classified into a compound (b1-1) having a hydroxyl group and not having a cyclic structure and a compound (b1-2) having a hydroxyl group and having a cyclic structure, both of which have a hydroxyl group. Thus, a great effect is exhibited in reducing curing shrinkage accompanying the polymerization reaction.
更に、耐熱性、あるいは耐湿熱性等の耐久性向上の点で、分子内に水酸基を有せず、かつ、1個以上の環状構造を有するα,β−エチレン性不飽和二重結合基含化合物(b2)を含有することが好ましい。
更に、(b1),(b2)以外のα,β−エチレン性不飽和二重結合基含有化合物(b3)も含有することができる。
Furthermore, an α, β-ethylenically unsaturated double bond group-containing compound which does not have a hydroxyl group in the molecule and has one or more cyclic structures from the viewpoint of improving durability such as heat resistance or heat and humidity resistance It is preferable to contain (b2).
Further, an α, β-ethylenically unsaturated double bond group-containing compound (b3) other than (b1) and (b2) can also be contained.
特に限定するものではないが、化合物(B)として使用可能な化合物としては、以下が挙げられる。 Although it does not specifically limit, The following is mentioned as a compound which can be used as a compound (B).
1個以上の水酸基を含有するα,β−エチレン性不飽和二重結合基含有化合物(b1)のうち、水酸基を有し、環状構造を有しない化合物(b1−1)としては、その構造中に水酸基を有するが、環状構造を有しないるものであれば特に制限はなく、例えば、(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸1−ヒドロキシプロピル、(メタ)アクリル酸2−ヒドロキシプロピル、(メタ)アクリル酸3−ヒドロキシプロピル、(メタ)アクリル酸1−ヒドロキシブチル、(メタ)アクリル酸2−ヒドロキシブチル、(メタ)アクリル酸3−ヒドロキシブチル、(メタ)アクリル酸4−ヒドロキシブチル、(メタ)アクリル酸6−ヒドロキシヘキシル、(メタ)アクリル酸8−ヒドロキシオクチル、シクロヘキサンジメタノールモノ(メタ)アクリル酸エステル、(メタ)アクリル酸10−ヒドロキシデシル、(メタ)アクリル酸12−ヒドロキシラウリル、(メタ)アクリル酸エチル−α−(ヒドロキシメチル)、単官能(メタ)アクリル酸グリセロール、あるいは(メタ)アクリル酸グリシジルラウリン酸エステル、(メタ)アクリル酸グリシジルオレイン酸エステル、(メタ)アクリル酸グリシジルステアリン酸エステル等の脂肪酸エステル系(メタ)アクリル酸エステル、あるいは、2−(アクリロイルオキシ)エチル6−ヒドロキシヘキサノネート等の前記水酸基含有α,β−エチレン性不飽和二重結合基含有化合物に対してε−カプロラクトンラクトンの開環付加により末端に水酸基を有する(メタ)アクリル酸エステル等の水酸基含有の脂肪族(メタ)アクリル酸エステル類; Of the α, β-ethylenically unsaturated double bond group-containing compound (b1) containing one or more hydroxyl groups, the compound (b1-1) having a hydroxyl group and not having a cyclic structure includes Is not particularly limited as long as it has a hydroxyl group but does not have a cyclic structure. For example, 2-hydroxyethyl (meth) acrylate, 1-hydroxypropyl (meth) acrylate, 2-methacrylic acid 2- Hydroxypropyl, 3-hydroxypropyl (meth) acrylate, 1-hydroxybutyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-methacrylic acid 4- Hydroxybutyl, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, cyclohexanedimethanol mono (meth) acrylate, T) Acrylic acid 10-hydroxydecyl, (meth) acrylic acid 12-hydroxylauryl, (meth) acrylic acid ethyl-α- (hydroxymethyl), monofunctional (meth) acrylic acid glycerol, or (meth) acrylic acid glycidyl lauric acid Acid esters, (meth) acrylic acid glycidyl oleates, (meth) acrylic acid glycidyl stearates and other fatty acid esters (meth) acrylic esters, or 2- (acryloyloxy) ethyl 6-hydroxyhexanoate, etc. Of the hydroxyl group-containing α, β-ethylenically unsaturated double bond group-containing compound in the above formula by the ring-opening addition of ε-caprolactone lactone to the hydroxyl group-containing aliphatic group (meta) acrylate (meth) acrylate ester or the like having a hydroxyl group at the terminal. ) Acrylic esters;
例えば、ヒドロキシエチルビニルエーテル、ヒドロキシプロピルビニルエーテル、ヒドロキシブチルビニルエーテル、ヒドロキシヘキシルビニルエーテル、ヒドロキシオクチルビニルエーテル、ヒドロキシデシルビニルエーテル、ヒドロキシドデシルビニルエーテル、ヒドロキシオクタデシルビニルエーテル、グリセリルビニルエーテル、トリエチレングリコールモノビニルエーテル、テトラエチレングリコールモノビニルエーテル、トリメチロールプロパンモノビニルエーテル、ペンタエリスリトールモノビニルエーテル等の水酸基含有の脂肪族ビニルエーテル類; For example, hydroxyethyl vinyl ether, hydroxypropyl vinyl ether, hydroxybutyl vinyl ether, hydroxyhexyl vinyl ether, hydroxyoctyl vinyl ether, hydroxydecyl vinyl ether, hydroxydodecyl vinyl ether, hydroxyoctadecyl vinyl ether, glyceryl vinyl ether, triethylene glycol monovinyl ether, tetraethylene glycol monovinyl ether, triethylene glycol Hydroxyl-containing aliphatic vinyl ethers such as methylolpropane monovinyl ether and pentaerythritol monovinyl ether;
例えば、(メタ)アリルアルコール、イソプロペニルアルコール、ジメチル(メタ)アリルアルコール、ヒドロキシエチル(メタ)アリルエーテル、ヒドロキシプロピル(メタ)アリルエーテル、ヒドロキシブチル(メタ)アリルエーテル、ヒドロキシヘキシル(メタ)アリルエーテル、ヒドロキシオクチル(メタ)アリルエーテル、ヒドロキシデシル(メタ)アリルエーテル、ヒドロキシドデシル(メタ)アリルエーテル、ヒドロキシオクタデシル(メタ)アリルエーテル、グリセリル(メタ)アリルエーテル等の水酸基含有の脂肪族(メタ)アリルアルコール類ないしは(メタ)アリルエーテル類; For example, (meth) allyl alcohol, isopropenyl alcohol, dimethyl (meth) allyl alcohol, hydroxyethyl (meth) allyl ether, hydroxypropyl (meth) allyl ether, hydroxybutyl (meth) allyl ether, hydroxyhexyl (meth) allyl ether Hydroxy-octyl (meth) allyl ether, hydroxydecyl (meth) allyl ether, hydroxydodecyl (meth) allyl ether, hydroxyoctadecyl (meth) allyl ether, glyceryl (meth) allyl ether, etc. Alcohols or (meth) allyl ethers;
例えば、プロペンジオール、ブテンジオール、ヘプテンジオール、オクテンジオール、ジ(メタ)アクリル酸グルセロール等の複数の水酸基を有するα,β−エチレン性不飽和二重結合基含有化合物類; For example, α, β-ethylenically unsaturated double bond group-containing compounds having a plurality of hydroxyl groups such as propenediol, butenediol, heptenediol, octenediol, and glycerol di (meth) acrylate;
例えば、N−ヒドロキシエチル(メタ)アクリルアミド、N−ヒドロキシプロピル(メタ)アクリルアミド、N−ヒドロキシブチル(メタ)アクリルアミド、N−ヒドロキシヘキシル(メタ)アクリルアミド、N−ヒドロキシオクチル(メタ)アクリルアミド等の水酸基含有の(メタ)アクリルアミド類; For example, hydroxyl groups such as N-hydroxyethyl (meth) acrylamide, N-hydroxypropyl (meth) acrylamide, N-hydroxybutyl (meth) acrylamide, N-hydroxyhexyl (meth) acrylamide, N-hydroxyoctyl (meth) acrylamide, etc. Of (meth) acrylamides;
例えば、ビニルアルコール等の水酸基とエテニル基を有する単量体類等が挙げられるが、特にこれらに限定されるものではない。これらは、1種だけを用いてもよいし、あるいは、複数種を併用してもよい。
化合物(b1−1)としては、基材との密着性の面より、(メタ)アクリル酸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、ε−カプロラクトン1〜2mol付加(メタ)アクリル酸2−ヒドロキシエチル等の炭素数2〜18であるα,β−エチレン性不飽和二重結合基含有化合物が特に好ましい。
Examples thereof include monomers having a hydroxyl group and an ethenyl group such as vinyl alcohol, but are not particularly limited thereto. These may use only 1 type or may use multiple types together.
As the compound (b1-1), from the viewpoint of adhesion to the substrate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, ε -Especially preferred are α, β-ethylenically unsaturated double bond group-containing compounds having 2 to 18 carbon atoms, such as 1 to 2 mol of caprolactone and 2-hydroxyethyl (meth) acrylate.
化合物(b1)のうち、水酸基を有し、環状構造を有する化合物(b1−2)は、水酸基と環状構造の双方を有するものであれば、特に制限はなく使用できる。化合物(b1−2)は、分子内に一つ以上の環構造を有しているため、水酸基を有していても耐熱性や耐湿熱性等の耐久性に加え、耐水性等の面から好ましい。
化合物(b1−2)としては、その構造中に水酸基と環状構造の双方を有するものであれば特に制限はなく、例えば、(メタ)アクリル酸1,2−シクロヘキサンジメタノール、(メタ)アクリル酸1,3−シクロヘキサンジメタノール、(メタ)アクリル酸1,4−シクロヘキサンジメタノール、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシメチル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシエチル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシプロピル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシブチル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシデシル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシオクタデシル、(メタ)アクリル酸モノヒドロキシエチルフタレート、(メタ)アクリル酸2−(4−ベンゾイル−3−ヒドロキシフェノキシ)エチル等の水酸基とヘテロ環以外の環状構造を有する(メタ)アクリル酸エステル類;
Among the compounds (b1), the compound (b1-2) having a hydroxyl group and having a cyclic structure can be used without particular limitation as long as it has both a hydroxyl group and a cyclic structure. Since compound (b1-2) has one or more ring structures in the molecule, it is preferable from the viewpoint of water resistance in addition to durability such as heat resistance and moist heat resistance even if it has a hydroxyl group. .
The compound (b1-2) is not particularly limited as long as it has both a hydroxyl group and a cyclic structure in its structure. For example, (meth) acrylic acid 1,2-cyclohexanedimethanol, (meth) acrylic acid 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol (meth) acrylate, 2-hydroxy-3-phenoxymethyl (meth) acrylate, 2-hydroxy-3-phenoxyethyl (meth) acrylate, ( 2-hydroxy-3-phenoxypropyl (meth) acrylate, 2-hydroxy-3-phenoxybutyl (meth) acrylate, 2-hydroxy-3-phenoxydecyl (meth) acrylate, 2-hydroxy- (meth) acrylate 3-phenoxyoctadecyl, (meth) acrylic acid monohydroxyethyl phthalate, (meth) acrylic acid 2- (4-benzoyl) (Meth) acrylic acid esters having a cyclic structure other than a hydroxyl group and a heterocyclic ring such as (-3-hydroxyphenoxy) ethyl;
例えば、2−ヒドロキシ−4−{2−(メタ)アクリロイルオキシ}エトキシベンゾフェノン、2−ヒドロキシ−4−{2−(メタ)アクリロイルオキシ}ブトキシベンゾフェノン、2,2'−ジヒドロキシ−4−{2−(メタ)アクリロイルオキシ}エトキシベンゾフェノン、2−ヒドロキシ−4−{2−(メタ)アクリロイルオキシ}エトキシ−4'−(2−ヒドロキシエトキシ)ベンゾフェノン等の水酸基含有ベンゾフェノン系(メタ)アクリル酸エステル類; For example, 2-hydroxy-4- {2- (meth) acryloyloxy} ethoxybenzophenone, 2-hydroxy-4- {2- (meth) acryloyloxy} butoxybenzophenone, 2,2′-dihydroxy-4- {2- Hydroxyl-containing benzophenone-based (meth) acrylic esters such as (meth) acryloyloxy} ethoxybenzophenone, 2-hydroxy-4- {2- (meth) acryloyloxy} ethoxy-4 ′-(2-hydroxyethoxy) benzophenone;
例えば、2−(2'−ヒドロキシ−5'−(メタ)アクリロイルオキシエチルフェニル)−2H−ベンゾトリアゾール、2−(2'−ヒドロキシ−5'−(メタ)アクリロイルオキシエチルフェニル)−5−クロロ−2H−ベンゾトリアゾール、2−(2'−ヒドロキシ−5'−(メタ)アクリロイルオキシプロピルフェニル)−2H−ベンゾトリアゾール;2−(2'−ヒドロキシ−5'−(メタ)アクリロイルオキシプロピルフェニル)−5−クロロ−2H−ベンゾトリアゾール、2−(2'−ヒドロキシ−3'−tert−ブチル−5'−(メタ)アクリロイルオキシエチルフェニル)−2H−ベンゾトリアゾール、及び2−(2'−ヒドロキシ−3'−tert−ブチル−5'−(メタ)アクリロイルオキシエチルフェニル)−5−クロロ−2H−ベンゾトリアゾール等の水酸基含有ベンゾトリアゾール系(メタ)アクリル酸エステル類; For example, 2- (2′-hydroxy-5 ′-(meth) acryloyloxyethylphenyl) -2H-benzotriazole, 2- (2′-hydroxy-5 ′-(meth) acryloyloxyethylphenyl) -5-chloro -2H-benzotriazole, 2- (2'-hydroxy-5 '-(meth) acryloyloxypropylphenyl) -2H-benzotriazole; 2- (2'-hydroxy-5'-(meth) acryloyloxypropylphenyl) -5-chloro-2H-benzotriazole, 2- (2'-hydroxy-3'-tert-butyl-5 '-(meth) acryloyloxyethylphenyl) -2H-benzotriazole, and 2- (2'-hydroxy -3'-tert-butyl-5 '-(meth) acryloyloxyethylphenyl) -5-chloro-2H-benzotriazole Triazole (meth) acrylic acid esters;
例えば、2,4−ジフェニル−6−[2−ヒドロキシ−4−{2−(メタ)アクリロイルオキシエトキシ}]−S−トリアジン、2,4−ビス(2−メチルフェニル)−6−[2−ヒドロキシ−4−{2−(メタ)アクリロイルオキシエトキシ}]−S−トリアジン、2,4−ビス(2−メトキシフェニル)−6−[2−ヒドロキシ−4−{2−(メタ)アクリロイルオキシエトキシ}]−S−トリアジン、2,4−ビス(2−エチルフェニル)−6−[2−ヒドロキシ−4−{2−(メタ)アクリロイルオキシエトキシ}]−S−トリアジン、2,4−ビス(2−エトキシフェニル)−6−[2−ヒドロキシ−4−{2−(メタ)アクリロイルオキシエトキシ}]−S−トリアジン、2,4−ビス(2,4−ジメチルフェニル)−6−[2−ヒドロキシ−4−{2−(メタ)アクリロイルオキシエトキシ}]−S−トリアジン、2,4−ビス(2,4−ジエトキシルフェニル)−6−[2−ヒドロキシ−4−{2−(メタ)アクリロイルオキシエトキシ}]−S−トリアジン、及び2,4−ビス(2,4−ジエチルフェニル)−6−[2−ヒドロキシ−4−{2−(メタ)アクリロイルオキシエトキシ})]−S−トリアジン等の水酸基含有トリアジン系(メタ)アクリル酸エステル類等が挙げられ、これらは、1種だけを用いてもよいし、あるいは、複数種を併用してもよい。 For example, 2,4-diphenyl-6- [2-hydroxy-4- {2- (meth) acryloyloxyethoxy}]-S-triazine, 2,4-bis (2-methylphenyl) -6- [2- Hydroxy-4- {2- (meth) acryloyloxyethoxy}]-S-triazine, 2,4-bis (2-methoxyphenyl) -6- [2-hydroxy-4- {2- (meth) acryloyloxyethoxy }]-S-triazine, 2,4-bis (2-ethylphenyl) -6- [2-hydroxy-4- {2- (meth) acryloyloxyethoxy}]-S-triazine, 2,4-bis ( 2-Ethoxyphenyl) -6- [2-hydroxy-4- {2- (meth) acryloyloxyethoxy}]-S-triazine, 2,4-bis (2,4-dimethylphenyl) -6- [2- Hydroxy-4- {2- (meth) acryloyloxyate Xyl}]-S-triazine, 2,4-bis (2,4-diethoxylphenyl) -6- [2-hydroxy-4- {2- (meth) acryloyloxyethoxy}]-S-triazine, and 2 , 4-Bis (2,4-diethylphenyl) -6- [2-hydroxy-4- {2- (meth) acryloyloxyethoxy})]-S-triazine and other hydroxyl group-containing triazine-based (meth) acrylic acid esters These may be used, and these may be used alone or in combination of two or more.
化合物(b1−2)としては、耐熱性や耐水性等の耐久性の面より、アクリル酸1,2−シクロヘキサンジメタノール、アクリル酸1,3−シクロヘキサンジメタノール、アクリル酸1,4−シクロヘキサンジメタノール、アクリル酸2−ヒドロキシ−3−フェノキシプロピル等が特に好ましい。 As the compound (b1-2), in view of durability such as heat resistance and water resistance, 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanediacrylate Methanol, 2-hydroxy-3-phenoxypropyl acrylate and the like are particularly preferable.
分子内に水酸基を有せず、かつ、1個以上の環状構造を有するα,β−エチレン性不飽和二重結合基含化合物(b2)は、分子内にヘテロ原子を含有しない環構造を有するα,β−エチレン性不飽和二重結合基含化合物(b2−1)と分子内にヘテロ原子を含有する環構造を有するα,β−エチレン性不飽和二重結合基含化合物(b2−2)があり、特に限定しないが、耐熱黄変性の点で、(b2−1)が好ましい。 The α, β-ethylenically unsaturated double bond group-containing compound (b2) having no hydroxyl group in the molecule and having one or more cyclic structures has a ring structure containing no heteroatoms in the molecule. α, β-ethylenically unsaturated double bond group-containing compound (b2-1) and α, β-ethylenically unsaturated double bond group-containing compound having a ring structure containing a hetero atom in the molecule (b2-2) (B2-1) is preferable from the viewpoint of heat-resistant yellowing.
化合物(b2−1)としては、その構造中にヘテロ環以外の環構造を有するものであれば特に制限はなく、例えば、(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸1−メチル−1−シクロペンチル、(メタ)アクリル酸1−エチル−1−シクロペンチル、(メタ)アクリル酸1−イソプロピル−1−シクロペンチル、(メタ)アクリル酸1−メチル−1−シクロヘキシル、(メタ)アクリル酸1−エチル−1−シクロヘキシル、(メタ)アクリル酸1−イソプロピル−1−シクロヘキシル、(メタ)アクリル酸1−エチル−1−シクロオクチル、(メタ)アクリル酸ベンジル、(メタ)アクリル酸iso−ボルニル、(メタ)アクリル酸フェニル、(メタ)アクリル酸2−フェノキシエチル、(メタ)アクリル酸2−オキソ−1,2−フェニルエチル、(メタ)アクリル酸2−オキソ−1,2−ジフェニルエチル、(メタ)アクリル酸1−ナフチル、(メタ)アクリル酸2−ナフチル、(メタ)アクリル酸1−ナフチルメチル、(メタ)アクリル酸1−アントリル、(メタ)アクリル酸2−アントリル、(メタ)アクリル酸9−アントリル、(メタ)アクリル酸9−アントリルメチル、(メタ)アクリル酸2−メチルアダマンチル−2−イル、(メタ)アクリル酸ジシクロペンタニル、(メタ)アクリル酸ジシクロペンテニル、(メタ)アクリル酸ジシクロペンテニルオキシエチル、(メタ)アクリル酸2−エチルアダマンチル−2−イル、(メタ)アクリル酸2−n−プロピルアダマンチル−2−イル、(メタ)アクリル酸2−イソプロピルアダマンチル−2−イル、(メタ)アクリル酸1−(アダマンタン−1−イル)−1−メチルエチル、(メタ)アクリル酸1−(アダマンタン−1−イル)−1−エチルエチル、(メタ)アクリル酸1−(アダマンタン−1−イル)−1−メチルプロピル、(メタ)アクリル酸1−(アダマンタン−1−イル)−1−エチルプロピル、(メタ)アクリル酸−5−オキソ−4−オキサ−トリシクロ[4.2.1.03,7]ノナ−2−イル、(メタ)アクリル酸−5−オキソ−4−オキサ−トリシクロ[5.2.1.03,8]デカ−2−イル、(メタ)アクリル酸ジヒドロ−α−ターピニル、(メタ)アクリル酸−6−オキソ−7−オキサ−ビシクロ[3.2.1]オクタ−2−イル、(メタ)アクリル酸−7−オキソ−8−オキサ−ビシクロ[3.3.1]オクタ−2−イル、2−(メタ)アクリロイルオキシエチルフタレート、2−(メタ)アクリロイルオキシプロピルフタレート、2−(メタ)アクリロイルオキシブチルフタレート、2−(メタ)アクリロイルオキシヘキシルフタレート、2−(メタ)アクリロイルオキシオクチルフタレート、2−(メタ)アクリロイルオキシデシルフタレート、2−(メタ)アクリロイルオキシエチルヘキサヒドロフタレート、(メタ)アクリル酸(3,4−エポキシシクロヘキシル)メチル、(メタ)アクリル酸−o−2−プロペニルフェニル、(メタ)アクリル酸シクロヘキシルグリシジルエーテル、(メタ)アクリル酸フェニルグリシジルエーテル等の(メタ)アクリル酸環状エステル類; The compound (b2-1) is not particularly limited as long as it has a ring structure other than a heterocyclic ring in its structure. For example, cyclohexyl (meth) acrylate, 1-methyl-1- (meth) acrylate Cyclopentyl, 1-ethyl-1-cyclopentyl (meth) acrylate, 1-isopropyl-1-cyclopentyl (meth) acrylate, 1-methyl-1-cyclohexyl (meth) acrylate, 1-ethyl (meth) acrylate 1-cyclohexyl, 1-isopropyl-1-cyclohexyl (meth) acrylate, 1-ethyl-1-cyclooctyl (meth) acrylate, benzyl (meth) acrylate, iso-bornyl (meth) acrylate, (meth) Phenyl acrylate, 2-methoxyethyl (meth) acrylate, 2-oxo-1,2-phenylethyl (meth) acrylate, (meth) acrylic acid 2 Oxo-1,2-diphenylethyl, 1-naphthyl (meth) acrylate, 2-naphthyl (meth) acrylate, 1-naphthylmethyl (meth) acrylate, 1-anthryl (meth) acrylate, (meth) acryl 2-anthryl acid, 9-anthryl (meth) acrylate, 9-anthrylmethyl (meth) acrylate, 2-methyladamantyl-2-yl (meth) acrylate, dicyclopentanyl (meth) acrylate, ( (Meth) acrylic acid dicyclopentenyl, (meth) acrylic acid dicyclopentenyloxyethyl, (meth) acrylic acid 2-ethyladamantyl-2-yl, (meth) acrylic acid 2-n-propyladamantyl-2-yl, 2- (meth) acrylic acid 2-isopropyladamantyl-2-yl, (meth) acrylic acid 1- (adamantan-1-yl) -1-methylethyl, (meth) acrylic acid -(Adamantan-1-yl) -1-ethylethyl, 1- (adamantan-1-yl) -1-methylpropyl (meth) acrylate, 1- (adamantan-1-yl) -1- (meth) acrylate Ethylpropyl, (meth) acrylic acid-5-oxo-4-oxa-tricyclo [4.2.1.0 3,7 ] non-2-yl, (meth) acrylic acid-5-oxo-4-oxa- Tricyclo [5.2.1.0 3,8 ] dec-2-yl, dihydro-α-terpinyl (meth) acrylate, (meth) acrylic acid-6-oxo-7-oxa-bicyclo [3.2. 1] Oct-2-yl, (meth) acrylic acid-7-oxo-8-oxa-bicyclo [3.3.1] oct-2-yl, 2- (meth) acryloyloxyethyl phthalate, 2- (meth ) Acryloyloxypropyl phthalate, 2- (meth) acrylo Yloxybutyl phthalate, 2- (meth) acryloyloxyhexyl phthalate, 2- (meth) acryloyloxyoctyl phthalate, 2- (meth) acryloyloxydecyl phthalate, 2- (meth) acryloyloxyethyl hexahydrophthalate, (meth) (Meth) acrylic acid cyclic such as (3,4-epoxycyclohexyl) methyl acrylate, (meth) acrylic acid-o-2-propenylphenyl, (meth) acrylic acid cyclohexyl glycidyl ether, (meth) acrylic acid phenyl glycidyl ether Esters;
例えば、N−(4−カルバモイルフェニル)(メタ)アクリルアミド、β−(2−フリル)(メタ)アクリルアミド、2,3−ビス(2−フリル)アクリルアミド、N−(9H−フルオレン−2−イル)(メタ)アクリルアミド、N−[(R)−1−フェニルエチル] (メタ)アクリルアミド、N−[(S)−1−フェニルエチル] (メタ)アクリルアミド、(Z)−N−メチル−3−(フェニル)(メタ)アクリルアミド、(Z)−3−(フェニル)(メタ)アクリルアミド、N,N−ジエチル−3−フェニル(メタ)アクリルアミド、(Z)−N,N−ジメチル−3−(フェニル)(メタ)アクリルアミド等の環状構造含有の(メタ)アクリルアミド類 For example, N- (4-carbamoylphenyl) (meth) acrylamide, β- (2-furyl) (meth) acrylamide, 2,3-bis (2-furyl) acrylamide, N- (9H-fluoren-2-yl) (Meth) acrylamide, N-[(R) -1-phenylethyl] (meth) acrylamide, N-[(S) -1-phenylethyl] (meth) acrylamide, (Z) -N-methyl-3- ( Phenyl) (meth) acrylamide, (Z) -3- (phenyl) (meth) acrylamide, N, N-diethyl-3-phenyl (meth) acrylamide, (Z) -N, N-dimethyl-3- (phenyl) (Meth) acrylamides containing cyclic structures such as (meth) acrylamide
例えば、(メタ)アクリル酸スルホフェノキシエチル、(メタ)アクリル酸スルホシクロヘキシル、(メタ)アクリル酸スルホベンジル、等のスルホニル基含有の(メタ)アクリル酸環状エステル類; For example, (meth) acrylic acid cyclic esters containing a sulfonyl group such as sulfophenoxyethyl (meth) acrylate, sulfocyclohexyl (meth) acrylate, sulfobenzyl (meth) acrylate;
例えば、(メタ)アクリロイルオキシエチルジメチルベンジルアンモニウム−p−トルエンスルホネート、(メタ)アクリロイルオキシエチルトリメチルアンモニウム−p−トルエンスルホネート、(メタ)アクリロイルアミノプロピルトリメチルアンモニウム−p−トルエンスルホネート、フェニル−2−(メタ)アクリロイルオキシエチルホスフェート等のスルホニル基含有の(メタ)アクリル酸環状エステル類の金属塩やアンモニウム塩類; For example, (meth) acryloyloxyethyldimethylbenzylammonium-p-toluenesulfonate, (meth) acryloyloxyethyltrimethylammonium-p-toluenesulfonate, (meth) acryloylaminopropyltrimethylammonium-p-toluenesulfonate, phenyl-2- ( Metal salts and ammonium salts of (meth) acrylic acid cyclic esters containing a sulfonyl group such as (meth) acryloyloxyethyl phosphate;
例えば、5−ビニルビシクロ[2.2.1]ヘプタ−2−エン、2,5−ビス(アリルオキシ)ノルボルナン、5−ビニル−2,3−オキシランノルボルナン、2−(2−プロペニル)ビシクロ[2.2.1]ヘプタン、5−ビニルビシクロ[2.2.1]ヘプタ−2−エン、2−エテニリデンアダマンタン、1−アリルアダマンタン、2−ビニル安息香酸、3−ビニル安息香酸、4−ビニル安息香酸、4−イソプロペニルベンゼンカルボン酸、桂皮酸、7−アミノ−3−ビニル−3−セフェム−4−カルボン酸、シクロヘキシルビニルエーテル、シクロヘキシルマレイミド、ビニルシクロヘキセンモノオキシラン等のアルケニル基含有の環状化合物類; For example, 5-vinylbicyclo [2.2.1] hept-2-ene, 2,5-bis (allyloxy) norbornane, 5-vinyl-2,3-oxirane norbornane, 2- (2-propenyl) bicyclo [2 2.1] heptane, 5-vinylbicyclo [2.2.1] hept-2-ene, 2-ethenylideneadamantane, 1-allyladamantane, 2-vinylbenzoic acid, 3-vinylbenzoic acid, 4-vinyl Cyclic compounds containing alkenyl groups such as benzoic acid, 4-isopropenylbenzenecarboxylic acid, cinnamic acid, 7-amino-3-vinyl-3-cephem-4-carboxylic acid, cyclohexyl vinyl ether, cyclohexylmaleimide, vinylcyclohexene monooxirane ;
例えば、スチレン、α−メチルスチレン、2−メチルスチレン、3−メチルスチレン、4−メチルスチレン、2−メトキシスチレン、3−メトキシスチレン、4−メトキシスチレン、4−t−ブトキシスチレン、4−t−ブトキシ−α−メチルスチレン、4−(2−エチル−2−プロポキシ)スチレン、4−(2−エチル−2−プロポキシ)−α−メチルスチレン、4−(1−エトキシエトキシ)スチレン、4−(1−エトキシエトキシ)−α−メチルスチレン、1−ブチルスチレン、1−クロロ−4−イソプロペニルベンゼンなどの芳香族ビニル系単量体類; For example, styrene, α-methylstyrene, 2-methylstyrene, 3-methylstyrene, 4-methylstyrene, 2-methoxystyrene, 3-methoxystyrene, 4-methoxystyrene, 4-t-butoxystyrene, 4-t- Butoxy-α-methylstyrene, 4- (2-ethyl-2-propoxy) styrene, 4- (2-ethyl-2-propoxy) -α-methylstyrene, 4- (1-ethoxyethoxy) styrene, 4- ( Aromatic vinyl monomers such as 1-ethoxyethoxy) -α-methylstyrene, 1-butylstyrene, 1-chloro-4-isopropenylbenzene;
例えば、シクロヘキシルビニルエーテル、シクロキシルメチルビニルエーテル、シクロヘキシルエチルビニルエーテル、メンチルビニルエーテル、テトラヒドロフルフリルビニルエーテル、ノルボルネニルビニルエーテル、1−アダマンチルビニルエーテル、2−アダマンチルビニルエーテル、フェニルビニルエーテル、ベンジルビニルエーテル、1−ナフチルビニルエーテル、2−ナフチルビニルエーテル等の環状ビニルエーテル類; For example, cyclohexyl vinyl ether, cyclohexyl methyl vinyl ether, cyclohexyl ethyl vinyl ether, menthyl vinyl ether, tetrahydrofurfuryl vinyl ether, norbornenyl vinyl ether, 1-adamantyl vinyl ether, 2-adamantyl vinyl ether, phenyl vinyl ether, benzyl vinyl ether, 1-naphthyl vinyl ether, 2- Cyclic vinyl ethers such as naphthyl vinyl ether;
例えば、ビニルフェニルペンチルエーテル、ビニルフェニルヘキシルエーテル、ビニルフェニルヘプチルエーテル、ビニルフェニルオクチルエーテル、ビニルフェニルノニルエーテル、ビニルフェニルデシルエーテル、ビニルフェニルウンデシルエーテル、ビニルフェニルドデシルエーテル、ビニルフェニルトリデシルエーテル、ビニルフェニルテトラデシルエーテル、ビニルフェニルペンタデシルエーテル、ビニルフェニルヘキサデシルエーテル、ビニルフェニルヘプタデシルエーテル、ビニルフェニルオクタデシルエーテル、ビニルフェニルノナデシルエーテル、ビニルフェニルエイコシルエーテル、ビニルフェニルヘンエイコシルエーテル、ビニルフェニルドコシルエーテル、ビニルフェニルメチルブチルエーテル、ビニルフェニルメチルペンチルエーテル、ビニルフェニルメチルヘキシルエーテル、ビニルフェニルメチルヘプチルエーテル、ビニルフェニルメチルオクチルエーテル、ビニルフェニルメチルノニルエーテル、ビニルフェニルメチルデシルエーテル、ビニルフェニルメチルウンデシルエーテル、ビニルフェニルメチルドデシルエーテル、ビニルフェニルメチルトリデシルエーテル、ビニルフェニルメチルテトラデシルエーテル、ビニルフェニルメチルペンタデシルエーテル、ビニルフェニルメチルヘキサデシルエーテル、ビニルフェニルメチルヘプタデシルエーテル、ビニルフェニルメチルオクタデシルエーテル、ビニルフェニルメチルノナデシルエーテル、ビニルフェニルメチルエイコシルエーテル、ビニルフェニルメチルヘンエイコシルエーテル、ビニルフェニルメチルドコシルエーテルなどの長鎖アルキル基を有する芳香族ビニルエーテル系単量体類; For example, vinyl phenyl pentyl ether, vinyl phenyl hexyl ether, vinyl phenyl heptyl ether, vinyl phenyl octyl ether, vinyl phenyl nonyl ether, vinyl phenyl decyl ether, vinyl phenyl undecyl ether, vinyl phenyl dodecyl ether, vinyl phenyl tridecyl ether, vinyl Phenyl tetradecyl ether, vinyl phenyl pentadecyl ether, vinyl phenyl hexadecyl ether, vinyl phenyl heptadecyl ether, vinyl phenyl octadecyl ether, vinyl phenyl nonadecyl ether, vinyl phenyl eicosyl ether, vinyl phenyl henecosyl ether, vinyl phenyl doco Sil ether, vinyl phenyl methyl butyl ether, vinyl phenyl Rupentyl ether, vinyl phenyl methyl hexyl ether, vinyl phenyl methyl heptyl ether, vinyl phenyl methyl octyl ether, vinyl phenyl methyl nonyl ether, vinyl phenyl methyl decyl ether, vinyl phenyl methyl undecyl ether, vinyl phenyl methyl dodecyl ether, vinyl phenyl methyl Tridecyl ether, vinyl phenylmethyl tetradecyl ether, vinyl phenyl methyl pentadecyl ether, vinyl phenyl methyl hexadecyl ether, vinyl phenyl methyl heptadecyl ether, vinyl phenyl methyl octadecyl ether, vinyl phenyl methyl nonadecyl ether, vinyl phenyl methyl eicosyl Ether, vinyl phenyl methyl henecosyl ether, vinyl Aromatic vinyl ether-based monomers having a long-chain alkyl groups such as E methylpropenylmethyl docosyl ether;
例えば、4−ビニル安息香酸ヘキシル、4−ビニル安息香酸オクチル、4−ビニル安息香酸ノニル、4−ビニル安息香酸デシル、4−ビニル安息香酸ドデシル、4−ビニル安息香酸テトラデシル、4−ビニル安息香酸ヘキサデシル、4−ビニル安息香酸オクタデシル、4−ビニル安息香酸エイコシル、4−ビニル安息香酸ドコシル、4−イソプロペニル安息香酸ヘキシル、4−イソプロペニル安息香酸オクチル、4−イソプロペニル安息香酸ノニル、4−イソプロペニル安息香酸デシル、4−イソプロペニル安息香酸ドデシル、4−イソプロペニル安息香酸テトラデシル、4−イソプロペニル安息香酸ヘキサデシル、4−イソプロペニル安息香酸オクタデシル、4−イソプロペニル安息香酸エイコシル、4−イソプロペニル安息香酸ドコシルなどの長鎖アルキル基を有するビニル安息香酸エステル系またはイソプロペニル安息香酸エステル系単量体類; For example, hexyl 4-vinylbenzoate, octyl 4-vinylbenzoate, nonyl 4-vinylbenzoate, decyl 4-vinylbenzoate, dodecyl 4-vinylbenzoate, tetradecyl 4-vinylbenzoate, hexadecyl 4-vinylbenzoate , Octadecyl 4-vinylbenzoate, eicosyl 4-vinylbenzoate, docosyl 4-vinylbenzoate, hexyl 4-isopropenylbenzoate, octyl 4-isopropenylbenzoate, nonyl 4-isopropenylbenzoate, 4-isopropenyl Decyl benzoate, 4-isopropenylbenzoic acid dodecyl, 4-isopropenylbenzoic acid tetradecyl, 4-isopropenylbenzoic acid hexadecyl, 4-isopropenylbenzoic acid octadecyl, 4-isopropenylbenzoic acid eicosyl, 4-isopropenylbenzoic acid Docosil How long vinylbenzoic acid ester having a chain alkyl group or isopropenyl benzoic acid ester monomers;
例えば、イソプロペニルフェニルメチルブチルエーテル、イソプロペニルフェニルメチルペンチルエーテル、イソプロペニルフェニルメチルヘキシルエーテル、イソプロペニルフェニルメチルヘプチルエーテル、イソプロペニルフェニルメチル オクチルエーテル、イソプロペニルフェニルメチルノニルエーテル、イソプロペニルフェニルメチルデシルエーテル、イソプロペニルフェニルメチルウンデシルエーテル、イソプロペニルフェニルメチルドデシルエーテル、イソプロペニルフェニルメチルトリデシルエーテル、イソプロペニルフェニルメチルテトラデシルエーテル、イソプロペニルフェニルメチルペンタデシルエーテル、イソプロペニルフェニルメチルヘキサデシルエーテル、イソプロペニルフェニルメチルヘプタデシルエーテル、イソプロペニルフェニルメチルオクタデシルエーテル、イソプロペニルフェニルメチルノナデシルエーテル、イソプロペニルフェニルメチルエイコシルエーテル、イソプロペニルフェニルメチルヘンエイコシルエーテル、イソプロペニルフェニルメチルドコシルエーテルなどの長鎖アルキル基を有するイソプロペニルフェニル系単量体類; For example, isopropenyl phenylmethyl butyl ether, isopropenyl phenyl methyl pentyl ether, isopropenyl phenyl methyl hexyl ether, isopropenyl phenyl methyl heptyl ether, isopropenyl phenyl methyl octyl ether, isopropenyl phenyl methyl nonyl ether, isopropenyl phenyl methyl decyl ether, Isopropenyl phenylmethyl undecyl ether, isopropenyl phenyl methyl dodecyl ether, isopropenyl phenyl methyl tridecyl ether, isopropenyl phenyl methyl tetradecyl ether, isopropenyl phenyl methyl pentadecyl ether, isopropenyl phenyl methyl hexadecyl ether, isopropenyl phenyl Methyl heptadecyl ether, Isopropenyl phenyl having a long chain alkyl group such as isopropenyl phenyl methyl octadecyl ether, isopropenyl phenyl methyl nonadecyl ether, isopropenyl phenyl methyl eicosyl ether, isopropenyl phenyl methyl heneicosyl ether, isopropenyl phenyl methyl docosyl ether Type monomers;
例えば、コハク酸ビニルフェニルノニル、ヘキサヒドロフタル酸ビニルフェニルメチルデシル、テレフタル酸ビニルフェニルエチルドデシルなどのジカルボン酸のモノ長鎖アルキルエステル系環状単量体類; For example, mono-long chain alkyl ester cyclic monomers of dicarboxylic acid such as vinyl phenylnonyl succinate, vinyl phenyl methyl decyl hexahydrophthalate, vinyl phenyl ethyl dodecyl terephthalate;
例えば、スチレンスルホン酸、2−プロペニルオキシベンゼンスルホン酸、2−メチル−2−プロペニルオキシベンゼンスルホン酸等のアルケニル基含有環状スルホン酸類; For example, alkenyl group-containing cyclic sulfonic acids such as styrenesulfonic acid, 2-propenyloxybenzenesulfonic acid, 2-methyl-2-propenyloxybenzenesulfonic acid;
例えば、スチレンスルホン酸アンモニウム、スチレンスルホン酸モノメチルアンモニウム、スチレンスルホン酸ジメチルアンモニウム、スチレンゼンスルホン酸トリメチルアンモニウム、スチレンスルホン酸テトラメチルアンモニム、スチレンスルホン酸エチルアンモニウム、スチレンスルホン酸ジエチルアンモニウム、スチレンスルホン酸トリエチルアンモニウム、スチレンスルホン酸テトラエチルアンモニウム、スチレンスルホン酸プロピルアンモニウム、スチレンスルホン酸ジプロピルアンモニウム、スチレンスルホン酸トリプロピルアンモニウム、スチレンスルホン酸ブチルアンモニウム、スチレンスルホン酸ペンチルアンモニウムまたはスチレンスルホン酸ヘキシルアンモニウム等のスチレンスルホン酸のアンモニウム塩類;
スチレンスルホン酸ナトリウム、スチレンスルホン酸カリウム、スチレンスルホン酸リチウム、スチレンスルホン酸マグネシウム、スチレンスルホン酸亜鉛、スチレンスルホン酸鉄等のスチレンスルホン酸の金属塩類;
ビニルオキシベンゼンスルホン酸アンモニウム、ビニルオキシベンゼンスルホン酸ナトリウム、ビニルオキシベンゼンスルホン酸カリウム等のアルケニル基含有ビニルオキシベンゼンスルホン酸の金属塩やアンモニウム塩類;
2−メチル−2−プロペニルオキシベンゼンスルホン酸アンモニウム、2−メチル−2−プロペニルオキシベンゼンスルホン酸ナトリウム、2−メチル−2−プロペニルオキシベンゼンスルホン酸カリウム等の2−メチル−2−プロペニルオキシベンゼンスルホン酸の金属塩やアンモニウム塩類等が挙げられる。
For example, ammonium styrene sulfonate, monomethyl ammonium styrene sulfonate, dimethyl ammonium styrene sulfonate, trimethyl ammonium styrene sulfonate, tetramethyl ammonium styrene sulfonate, ethyl ammonium styrene sulfonate, diethyl ammonium styrene sulfonate, triethyl styrene sulfonate Styrenesulfonic acid such as ammonium, tetraethylammonium styrenesulfonate, propylammonium styrenesulfonate, dipropylammonium styrenesulfonate, tripropylammonium styrenesulfonate, butylammonium styrenesulfonate, pentylammonium styrenesulfonate or hexylammonium styrenesulfonate Ammonium salts of
Metal salts of styrene sulfonic acid such as sodium styrene sulfonate, potassium styrene sulfonate, lithium styrene sulfonate, magnesium styrene sulfonate, zinc styrene sulfonate, iron styrene sulfonate;
Metal salts and ammonium salts of alkenyl group-containing vinyloxybenzenesulfonic acid such as ammonium vinyloxybenzenesulfonate, sodium vinyloxybenzenesulfonate, potassium vinyloxybenzenesulfonate, etc .;
2-methyl-2-propenyloxybenzenesulfonate ammonium, 2-methyl-2-propenyloxybenzenesulfonate sodium, 2-methyl-2-propenyloxybenzenesulfonate potassium and the like 2-methyl-2-propenyloxybenzenesulfonate Examples include acid metal salts and ammonium salts.
また、例えば、o−ジ(メタ)アリルビスフェノールA、芳香環構造が水素添加された水添ビスフェノールA等もα,β−不飽和二重結合基を有すれば、化合物(b2−1)に含まれる。これらは、1種だけを用いてもよいし、あるいは、複数種を併用してもよい。 In addition, for example, o-di (meth) allylbisphenol A, hydrogenated bisphenol A in which an aromatic ring structure is hydrogenated, and the like have an α, β-unsaturated double bond group, compound (b2-1) included. These may use only 1 type or may use multiple types together.
化合物(b2−1)としては、耐熱性や耐水性等の耐久性の面より、アクリル酸シクロヘキシル、アクリル酸フェニル、アクリル酸ベンジル、アクリル酸2−フェノキシエチル、アクリル酸iso−ボルニル、アクリル酸ジシクロペンタニル、ジアクリル酸ジシクロペンタニル、アクリル酸ジシクロペンテニル、ジアクリル酸ジシクロペンテニル、アクリル酸2−エチルアダマンチル−2−イルが特に好ましい。 As the compound (b2-1), from the viewpoint of durability such as heat resistance and water resistance, cyclohexyl acrylate, phenyl acrylate, benzyl acrylate, 2-phenoxyethyl acrylate, iso-bornyl acrylate, diacrylate acrylate Particularly preferred are cyclopentanyl, dicyclopentanyl diacrylate, dicyclopentenyl acrylate, dicyclopentenyl diacrylate, and 2-ethyladamantyl-2-yl acrylate.
化合物(b2−2)としては、その構造中にヘテロ環構造を有するものであれば、特に制限はなく、例えば、ペンタメチルピペリジニル(メタ)アクリレート、4−(ピリミジン−2−イル)ピペラジン−1−イル(メタ)アクリレート等の窒素原子含有のヘテロ環状(メタ)アクリル酸エステル類; The compound (b2-2) is not particularly limited as long as it has a heterocyclic structure in its structure. For example, pentamethylpiperidinyl (meth) acrylate, 4- (pyrimidin-2-yl) piperazine Heterocyclic (meth) acrylic acid esters containing nitrogen atoms such as -1-yl (meth) acrylate;
例えば、1−ビニルピロール、1−ビニル−2−イミダゾリン、1−ビニル−2−メチル−2−イミダゾリン、1−ビニルイミダゾール、1−ビニル−1H−ピラゾール、1−ビニル−3,5―ジメチル―1H−ピラゾール、3−メチル−5−フェニル−1−ビニルピラゾール、1−ビニルインドール、1−ビニル−2−メチル−1H−インドール、1−ビニルイソインドール、1−ビニル−1H−ベンゾイミダゾール、1−ビニルインダゾール、1−ビニルキノリン、1−ビニルイソキサリン、1−ビニルキナゾリン、1−ビニルシンノリン、1−ビニルカルバゾール、1,1'−ジビニル−2,2'−ビ(1H−イミダゾール)、N−ビニル−2−ピロリドン、N−ビニル−ε−カプロラクタム、1−ビニルピリジン−2(1H)−オン、1−ビニル−2(1H)−ピリジンチオン等の窒素原子含有のヘテロ環を有するビニル基含有化合物類; For example, 1-vinylpyrrole, 1-vinyl-2-imidazoline, 1-vinyl-2-methyl-2-imidazoline, 1-vinylimidazole, 1-vinyl-1H-pyrazole, 1-vinyl-3,5-dimethyl- 1H-pyrazole, 3-methyl-5-phenyl-1-vinylpyrazole, 1-vinylindole, 1-vinyl-2-methyl-1H-indole, 1-vinylisoindole, 1-vinyl-1H-benzimidazole, 1 -Vinylindazole, 1-vinylquinoline, 1-vinylisoxaline, 1-vinylquinazoline, 1-vinylcinnoline, 1-vinylcarbazole, 1,1'-divinyl-2,2'-bi (1H-imidazole) N-vinyl-2-pyrrolidone, N-vinyl-ε-caprolactam, 1-vinylpyridin-2 (1H) -one, 1-bi Le -2 (IH) - vinyl group-containing compounds having a heterocyclic nitrogen-containing, such as pyridinethione;
例えば、1−(メタ)アリル−1H−イミダゾール、1−(メタ)アリル−2−メチル−1H−イミダゾール、1−(メタ)アリル−3−メチル−1H−イミダゾール−3−イウム、1−(メタ)アリル−3−エチル−1H−イミダゾール−3−イウム、5−ブロモ−1−(メタ)アリル−1H−ピラゾール、1−(メタ)アリルピペラジン、1−(メタ)アリル−5,5−ジエチルピリミジン、N−(メタ)アリル−s−トリアジン−2,4,6−トリアミン、N−(メタ)アリル−4,6−ジクロロ−1,3−5−トリアジン−2−アミン、1−ベンジル−2−ビニルピペラジン、1−ベンジル−3−ビニルピペラジン、1、4−ジメチル−3−ビニルピペラジン、2−ビニル−4,6−ジアミノ−1,3,5−トリアジン、6−ビニル−1,3,5―ジメチル―2,4−ジアミン、3−ビニル−1,2,4,5−テトラジン等の窒素原子含有の六員環を有するビニル基含有化合物類; For example, 1- (meth) allyl-1H-imidazole, 1- (meth) allyl-2-methyl-1H-imidazole, 1- (meth) allyl-3-methyl-1H-imidazol-3-ium, 1- ( (Meth) allyl-3-ethyl-1H-imidazol-3-ium, 5-bromo-1- (meth) allyl-1H-pyrazole, 1- (meth) allylpiperazine, 1- (meth) allyl-5,5- Diethylpyrimidine, N- (meth) allyl-s-triazine-2,4,6-triamine, N- (meth) allyl-4,6-dichloro-1,3-5-triazine-2-amine, 1-benzyl 2-vinylpiperazine, 1-benzyl-3-vinylpiperazine, 1,4-dimethyl-3-vinylpiperazine, 2-vinyl-4,6-diamino-1,3,5-triazine, 6-vinyl-1, 3,5-dimethyl- , 4-diamine, 3-vinyl-1,2,4,5-vinyl group-containing compounds having a six-membered ring nitrogen-containing, such as tetrazine;
例えば、1−ビニル−1H−ベンゾイミダゾール、1−ビニル−5,6−ジメチル−1H−ベンゾイミダゾール、1−ビニルインダゾール、1−ビニルキノリン、1−ビニルキノリン、1−ビニルイソキノリン、1−ビニルイソキサリン、1−ビニルキノキサリン、1−ビニルキナゾリン、1−ビニルシンノリン、1−(メタ)アリル−1H−ベンゾイミダゾール、1−(メタ)アリル−3−メチル−1H−インダゾール、1−(メタ)アリル−4−メチル−1H−インダゾール、N−(メタ)アリルキノリン−4−アミン、ジ(メタ)アリルキノリン、1,2−ジ(メタ)アリル−1,2−ジヒドロイソキノリン等の窒素原子含有のヘテロ多環系エテニル基含有化合物類; For example, 1-vinyl-1H-benzimidazole, 1-vinyl-5,6-dimethyl-1H-benzimidazole, 1-vinylindazole, 1-vinylquinoline, 1-vinylquinoline, 1-vinylisoquinoline, 1-vinyliso Xaline, 1-vinylquinoxaline, 1-vinylquinazoline, 1-vinylcinnoline, 1- (meth) allyl-1H-benzimidazole, 1- (meth) allyl-3-methyl-1H-indazole, 1- (meta Nitrogen atoms such as allyl-4-methyl-1H-indazole, N- (meth) allylquinolin-4-amine, di (meth) allylquinoline, 1,2-di (meth) allyl-1,2-dihydroisoquinoline Containing heteropolycyclic ethenyl group-containing compounds;
例えば、1−メチル−4,5−ジビニル−1H−イミダゾール等の窒素原子含有のヘテロ環構造と二個以上のビニル基を有する化合物類; For example, compounds having a nitrogen atom-containing heterocyclic structure and two or more vinyl groups such as 1-methyl-4,5-divinyl-1H-imidazole;
例えば、1−(メタ)アリル−3,5−ジメチル−1H−ピラゾール、1−(1−メチルプロピル)−5−(メタ)アリルピリミジン、1−(メタ)アリル−5−イソプロピルピリミジン、1−(メタ)アリルピリジン、1−(メタ)アリルピリジン、3,6−ジヒドロ−1−(メタ)アリルピリジン等の窒素原子含有のヘテロ環状構造を有する(メタ)アリル基含有化合物類; For example, 1- (meth) allyl-3,5-dimethyl-1H-pyrazole, 1- (1-methylpropyl) -5- (meth) allylpyrimidine, 1- (meth) allyl-5-isopropylpyrimidine, 1- (Meth) allyl group-containing compounds having a nitrogen atom-containing heterocyclic structure such as (meth) allylpyridine, 1- (meth) allylpyridine, 3,6-dihydro-1- (meth) allylpyridine;
例えば、2−(メタ)アリル−1H−インドール、3−(メタ)アリル−1H−インドール、2−(メタ)アリルインダゾール、3−フェニル−4−(メタ)アリルイソキノリン、9−(メタ)アリル−9H−カルバゾール等の窒素原子含有のヘテロ多環構造を有する(メタ)アリル基含有化合物類; For example, 2- (meth) allyl-1H-indole, 3- (meth) allyl-1H-indole, 2- (meth) allylindazole, 3-phenyl-4- (meth) allylisoquinoline, 9- (meth) allyl (Meth) allyl group-containing compounds having a heteropolycyclic structure containing a nitrogen atom, such as -9H-carbazole;
例えば、イミド(メタ)アクリレート、2−(4−オキサゾリン−3−イル)エチル(メタ)アクリレート、ジ(メタ)アクリル酸エトキシ化イソシアヌル酸、トリ(メタ)アクリル酸エトキシ化イソシアヌル酸、ε−カプロラクトン変性トリス−(2−アクリロイルオキシエチル)イソシアヌレート、ジ(メタ)アクリル酸イソシアヌル酸エチレンオキサイド変性、トリ(メタ)アクリル酸イソシアヌル酸エチレンオキサイド変性等の窒素原子以外に酸素原子を含むヘテロ環状構造を有する(メタ)アクリル酸エステル類; For example, imide (meth) acrylate, 2- (4-oxazolin-3-yl) ethyl (meth) acrylate, di (meth) acrylic acid ethoxylated isocyanuric acid, tri (meth) acrylic acid ethoxylated isocyanuric acid, ε-caprolactone Heterocyclic structures containing oxygen atoms in addition to nitrogen atoms such as modified tris- (2-acryloyloxyethyl) isocyanurate, di (meth) acrylic acid isocyanuric acid ethylene oxide modification, tri (meth) acrylic acid isocyanuric acid ethylene oxide modification (Meth) acrylic acid esters having;
例えば、4−アクリロイルモルホリン、N−[2−(1H−イミダゾール−5−イル)エチル] (メタ)アクリルアミド、N−(オキセタン−3−イルメトキシメチル)(メタ)アクリルアミド、N−(オキセタン−2−イルメトキシメチル)(メタ)アクリルアミド等のヘテロ環状アクリルアミド類; For example, 4-acryloylmorpholine, N- [2- (1H-imidazol-5-yl) ethyl] (meth) acrylamide, N- (oxetane-3-ylmethoxymethyl) (meth) acrylamide, N- (oxetane-2 -Heterocyclic acrylamides such as (ylmethoxymethyl) (meth) acrylamide;
例えば、メチルマレイミド、エチルマレイミド、プロピルマレイミド、ブチルマレイミド、オクチルマレイミド、ドデシルマレイミド、ステアリルマレイミド、フェニルマレイミド、シクロヘキシルマレイミドなどの窒素原子と酸素原子の双方を有するマレイミド誘導体類; For example, maleimide derivatives having both nitrogen and oxygen atoms, such as methylmaleimide, ethylmaleimide, propylmaleimide, butylmaleimide, octylmaleimide, dodecylmaleimide, stearylmaleimide, phenylmaleimide, cyclohexylmaleimide;
例えば、2−ビニルオキサゾール、2−フェニル−4−ビニルオキサゾール、2−フェニル−5−ビニルオキサゾール、5−エトキシ−2−ビニルオキサゾール、3−ビニル−5−ニトロソオキサゾール、2−ビニル−4,5−ジフェニルオキサゾール、2−ビニル−2−オキサゾリン、4,4−ジメチル−2−ビニル−2−オキサゾリン−5−オン、2−ビニルベンゾオキサゾール等の窒素原子以外に酸素原子を含むヘテロ環状構造を有するビニル基含有化合物類; For example, 2-vinyl oxazole, 2-phenyl-4-vinyl oxazole, 2-phenyl-5-vinyl oxazole, 5-ethoxy-2-vinyl oxazole, 3-vinyl-5-nitrosoxazole, 2-vinyl-4,5 -It has a heterocyclic structure containing an oxygen atom in addition to a nitrogen atom such as diphenyloxazole, 2-vinyl-2-oxazoline, 4,4-dimethyl-2-vinyl-2-oxazolin-5-one, 2-vinylbenzoxazole Vinyl group-containing compounds;
例えば、(メタ)アクリル酸グリシジル、(メタ)アクリル酸(3,4−エポキシシクロヘキシル)メチル、(メタ)アクリル酸(3−メチル−3−オキセタニル)メチル、(メタ)アクリル酸テトラヒドロフルフリル、(メタ)アクリル酸−2−オキソテトラヒドロピラン−4−イル、(メタ)アクリル酸−4−メチル−2−オキソテトラヒドロピラン−4−イル、(メタ)アクリル酸−4−エチル−2−オキソテトラヒドロピラン−4−イル、(メタ)アクリル酸−4−プロピル−2−オキソテトラヒドロピラン−4−イル、(メタ)アクリル酸−5−オキソテトラヒドロフラン−3−イル、(メタ)アクリル酸−2,2−ジメチル−5−オキソテトラヒドロフラン−3−イル、(メタ)アクリル酸−4,4−ジメチル−5−オキソテトラヒドロフラン−3−イル、(メタ)アクリル酸−2−オキソテトラヒドロフラン−3−イル、(メタ)アクリル酸−4,4−ジメチル−2−オキソテトラヒドロフラン−3−イル、(メタ)アクリル酸−5,5−ジメチル−2−オキソテトラヒドロフラン−3−イル、(メタ)アクリル酸−2−オキソテトラヒドロフラン−3−イル、(メタ)アクリル酸−5−オキソテトラヒドロフラン−2−イルメチル、(メタ)アクリル酸−3,3−ジメチル−5−オキソテトラヒドロフラン−2−イルメチル、(メタ)アクリル酸−4,4−ジメチル−5−オキソテトラヒドロフラン−2−イルメチル等の酸素原子を有するヘテロ環含有(メタ)アクリル酸エステル類; For example, glycidyl (meth) acrylate, (3,4-epoxycyclohexyl) methyl (meth) acrylate, (3-methyl-3-oxetanyl) methyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, ( (Meth) acrylic acid-2-oxotetrahydropyran-4-yl, (meth) acrylic acid-4-methyl-2-oxotetrahydropyran-4-yl, (meth) acrylic acid-4-ethyl-2-oxotetrahydropyran -4-yl, (meth) acrylic acid-4-propyl-2-oxotetrahydropyran-4-yl, (meth) acrylic acid-5-oxotetrahydrofuran-3-yl, (meth) acrylic acid-2,2- Dimethyl-5-oxotetrahydrofuran-3-yl, (meth) acrylic acid-4,4-dimethyl-5-oxotetrahydrofuran-3-yl, (meth) acrylic acid 2-Oxotetrahydrofuran-3-yl lylate, (meth) acrylic acid-4,4-dimethyl-2-oxotetrahydrofuran-3-yl, (meth) acrylic acid-5,5-dimethyl-2-oxotetrahydrofuran 3-yl, (meth) acrylic acid-2-oxotetrahydrofuran-3-yl, (meth) acrylic acid-5-oxotetrahydrofuran-2-ylmethyl, (meth) acrylic acid-3,3-dimethyl-5-oxotetrahydrofuran Heterocycle-containing (meth) acrylic acid esters having an oxygen atom, such as 2-ylmethyl and (meth) acrylic acid-4,4-dimethyl-5-oxotetrahydrofuran-2-ylmethyl;
例えば、グリシジルシンナマート、アリルグリシジルエーテル、1,3−ブタジエンモノオキシラン等のグリシジル基含有ビニルエステル類; For example, glycidyl group-containing vinyl esters such as glycidyl cinnamate, allyl glycidyl ether, 1,3-butadiene monooxirane;
例えば、2−ビニルチアゾ−ル、4−メチル−5−ビニルチアゾール、2−ビニルベンゾチアゾール、2−[2−(1−ナフチル)ビニル]ベンゾチアゾール、2−[2−(ジメチルアミノ)ビニル]ベンゾチアゾール等の窒素原子以外に硫黄原子を含むヘテロ環状構造を有するビニル基含有化合物類等が挙げられ、これらは、1種だけを用いてもよいし、あるいは、複数種を併用してもよい。 For example, 2-vinylthiazol, 4-methyl-5-vinylthiazole, 2-vinylbenzothiazole, 2- [2- (1-naphthyl) vinyl] benzothiazole, 2- [2- (dimethylamino) vinyl] benzo Examples thereof include vinyl group-containing compounds having a heterocyclic structure containing a sulfur atom in addition to a nitrogen atom such as thiazole, and these may be used alone or in combination of two or more.
化合物(b2−2)としては、耐熱性や耐水性等の耐久性の面より、アクリル酸グリシジル、メタクリル酸グリシジル、メタクリル酸(3,4−エポキシシクロヘキシル)メチル、4−アクリロイルモルホリン、1−ビニルイミダゾール、N−ビニル−ε−カプロラクタム、1−ビニルピリジン−2(1H)−オン、ジ(メタ)アクリル酸エトキシ化イソシアヌル酸、トリ(メタ)アクリル酸エトキシ化イソシアヌル酸が特に好ましい。 As the compound (b2-2), from the viewpoint of durability such as heat resistance and water resistance, glycidyl acrylate, glycidyl methacrylate, (3,4-epoxycyclohexyl) methyl methacrylate, 4-acryloylmorpholine, 1-vinyl Particularly preferred are imidazole, N-vinyl-ε-caprolactam, 1-vinylpyridin-2 (1H) -one, di (meth) acrylic acid ethoxylated isocyanuric acid, and tri (meth) acrylic acid ethoxylated isocyanuric acid.
また、(b1)あるいは、(b2)以外の化合物(b3)としては、その構造中にα,β−エチレン性不飽和二重結合基を有するものであれば特に制限はなく、 The compound (b3) other than (b1) or (b2) is not particularly limited as long as it has an α, β-ethylenically unsaturated double bond group in its structure.
例えば、(メタ)アクリル酸メチル、(メタ)アクリル酸エチル、(メタ)アクリル酸1−プロピル、(メタ)アクリル酸2−プロピル、(メタ)アクリル酸n−ブチル、(メタ)アクリル酸sec−ブチル、(メタ)アクリル酸iso−ブチル、(メタ)アクリル酸tert−ブチル、(メタ)アクリル酸n−アミル、(メタ)アクリル酸iso−アミル、(メタ)アクリル酸n−ヘキシル、(メタ)アクリル酸2−エチルヘキシル、(メタ)アクリル酸n−オクチル、(メタ)アクリル酸iso−オクチル、(メタ)アクリル酸n−ノニル、(メタ)アクリルiso−ノニル、(メタ)アクリル酸デシル、(メタ)アクリル酸ドデシル、(メタ)アクリル酸オクタデシル、(メタ)アクリル酸ラウリル、(メタ)アクリル酸ステアリルなどの(メタ)アクリル酸アルキルエステル類; For example, methyl (meth) acrylate, ethyl (meth) acrylate, 1-propyl (meth) acrylate, 2-propyl (meth) acrylate, n-butyl (meth) acrylate, sec- (meth) acrylic acid Butyl, iso-butyl (meth) acrylate, tert-butyl (meth) acrylate, n-amyl (meth) acrylate, iso-amyl (meth) acrylate, n-hexyl (meth) acrylate, (meth) 2-ethylhexyl acrylate, n-octyl (meth) acrylate, iso-octyl (meth) acrylate, n-nonyl (meth) acrylate, (meth) acrylic iso-nonyl, decyl (meth) acrylate, (meth) ) Alkyl (meth) acrylates such as dodecyl acrylate, octadecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate;
例えば、(メタ)アクリル酸(メタ)アリル、(メタ)アクリル酸1−ブテニル、(メタ)アクリル酸2−ブテニル、(メタ)アクリル酸3−ブテニル、(メタ)アクリル酸1,3−メチル−3−ブテニル、(メタ)アクリル酸2−クロル2−プロペニル、(メタ)アクリル酸3−クロル2−プロペニル、(メタ)アクリル酸2−(2−プロペニルオキシ)エチル、(メタ)アクリル酸2−プロペニルラクチル、(メタ)アクリル酸3,7−ジメチルオクタ−6−エン−1−イル、(メタ)アクリル酸(E)−3,7−ジメチルオクタ−2,6−ジエン−1−イル、(メタ)アクリル酸ロジニル、(メタ)アクリル酸シンナミル、(メタ)アクリル酸ビニル等のさらに不飽和基を含有する(メタ)アクリル酸エステル類; For example, (meth) acrylic acid (meth) allyl, (meth) acrylic acid 1-butenyl, (meth) acrylic acid 2-butenyl, (meth) acrylic acid 3-butenyl, (meth) acrylic acid 1,3-methyl- 3-butenyl, 2-chloro-2-propenyl (meth) acrylate, 3-chloro-2-propenyl (meth) acrylate, 2- (2-propenyloxy) ethyl (meth) acrylate, 2- (meth) acrylic acid 2- Propenyl lactyl, 3,7-dimethyloct-6-en-1-yl (meth) acrylate, (meth) acrylic acid (E) -3,7-dimethyloct-2,6-dien-1-yl, (Meth) acrylic acid esters further containing an unsaturated group such as rosinyl (meth) acrylate, cinnamyl (meth) acrylate, vinyl (meth) acrylate;
例えば、(メタ)アクリル酸パーフルオロメチル、(メタ)アクリル酸パーフルオロエチル、(メタ)アクリル酸パーフルオロプロピル、(メタ)アクリル酸パーフルオロブチル、(メタ)アクリル酸パーフルオロオクチル、(メタ)アクリル酸トリフルオロメチルメチル、(メタ)アクリル酸2−トリフルオロメチルエチル、(メタ)アクリル酸ジパーフルオロメチルメチル、(メタ)アクリル酸2−パーフルオロエチルエチル、(メタ)アクリル酸2−パーフルオロメチル−2−パーフルオロエチルメチル、(メタ)アクリル酸トリパーフルオロメチルメチル、(メタ)アクリル酸2−パーフルオロエチル−2−パーフルオロブチルエチル、(メタ)アクリル酸2−パーフルオロヘキシルエチル、(メタ)アクリルプロペン酸2−パーフルオロデシルエチル、(メタ)アクリル酸2−パーフルオロヘキサデシルエチルなどの(メタ)アクリル酸パーフルオロアルキルエステル類; For example, perfluoromethyl (meth) acrylate, perfluoroethyl (meth) acrylate, perfluoropropyl (meth) acrylate, perfluorobutyl (meth) acrylate, perfluorooctyl (meth) acrylate, (meth) Trifluoromethylmethyl acrylate, 2-trifluoromethylethyl (meth) acrylate, diperfluoromethylmethyl (meth) acrylate, 2-perfluoroethylethyl (meth) acrylate, 2-par (meth) acrylate Fluoromethyl-2-perfluoroethylmethyl, triperfluoromethylmethyl (meth) acrylate, 2-perfluoroethyl-2-perfluorobutylethyl (meth) acrylate, 2-perfluorohexylethyl (meth) acrylate , (Meth) acrylic propenoic acid 2-perfluorodecylethyl, (meth) acrylic acid 2 (Meth) acrylic acid such as perfluoro hexadecyl ethyl perfluoroalkyl esters;
例えば、(メタ)アクリル酸2−メトキシエチル、(メタ)アクリル酸2−エトキシエチル、(メタ)アクリル酸2−プロポキシエチル、(メタ)アクリル酸3−プロポキシエチル、(メタ)アクリル酸2−ブトキシエチル、(メタ)アクリル酸3−ブトキシエチル、(メタ)アクリル酸4−ブトキシエチル等のアルコキシ基含有(メタ)アクリル酸エステル類; For example, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-propoxyethyl (meth) acrylate, 3-propoxyethyl (meth) acrylate, 2-butoxy (meth) acrylate Alkoxy group-containing (meth) acrylic esters such as ethyl, 3-butoxyethyl (meth) acrylate, 4-butoxyethyl (meth) acrylate;
例えば、(メタ)アクリル酸のアルキレンオキサイド付加物などのアルキレンオキサイド含有(メタ)アクリル酸誘導体類; For example, alkylene oxide-containing (meth) acrylic acid derivatives such as an alkylene oxide adduct of (meth) acrylic acid;
例えば、(メタ)アクリル酸(メトキシカルボニル)メチル、(メタ)アクリル酸(メトキシカルボニル)エチル、(メタ)アクリル酸(メトキシカルボニル)プロピル、(メタ)アクリル酸(メトキシカルボニル)ブチル、(メタ)アクリル酸(メトキシカルボニル)デシル、(メタ)アクリル酸(エトキシカルボニル)メチル、(メタ)アクリル酸(エトキシカルボニル)エチル、(メタ)アクリル酸(エトキシカルボニル)プロピル、(メタ)アクリル酸(エトキシカルボニル)ブチル、(メタ)アクリル酸(エトキシカルボニル)ヘキシル、(メタ)アクリル酸(エトキシカルボニル)オクチル、(メタ)アクリル酸2−(エトキシカルボニルオキシ)エチル、(メタ)アクリル酸2−(エトキシカルボニルオキシ)プロピル、(メタ)アクリル酸2−(エトキシカルボニルオキシ)ブチル、(メタ)アクリル酸2−(エトキシカルボニルオキシ)ヘキシル、(メタ)アクリル酸2−(エトキシカルボニルオキシ)オクチル、(メタ)アクリル酸2−(プロポキシカルボニルオキシ)エチル、(メタ)アクリル酸2−(ブトキシカルボニルオキシ)エチル、(メタ)アクリル酸2−(ブトキシカルボニルオキシ)ブチル、(メタ)アクリル酸2−(オクチルオキシカルボニルオキシ)エチル、(メタ)アクリル酸2−(オクチルオキシカルボニルオキシ)ブチル等のカルボニル基を1つ有する脂肪族系の(メタ)アクリル酸エステル類; For example, (meth) acrylic acid (methoxycarbonyl) methyl, (meth) acrylic acid (methoxycarbonyl) ethyl, (meth) acrylic acid (methoxycarbonyl) propyl, (meth) acrylic acid (methoxycarbonyl) butyl, (meth) acrylic Acid (methoxycarbonyl) decyl, (meth) acrylic acid (ethoxycarbonyl) methyl, (meth) acrylic acid (ethoxycarbonyl) ethyl, (meth) acrylic acid (ethoxycarbonyl) propyl, (meth) acrylic acid (ethoxycarbonyl) butyl , (Meth) acrylic acid (ethoxycarbonyl) hexyl, (meth) acrylic acid (ethoxycarbonyl) octyl, 2- (ethoxycarbonyloxy) ethyl (meth) acrylate, 2- (ethoxycarbonyloxy) propyl (meth) acrylate , (Meth) acrylic acid 2- (ethoxycarbonyloxy) butyl, (meth) acrylic acid 2- ( (Toxycarbonyloxy) hexyl, 2- (ethoxycarbonyloxy) octyl (meth) acrylate, 2- (propoxycarbonyloxy) ethyl (meth) acrylate, 2- (butoxycarbonyloxy) ethyl (meth) acrylate, (meth ) Fatty acid having one carbonyl group such as 2- (butoxycarbonyloxy) butyl acrylate, 2- (octyloxycarbonyloxy) ethyl (meth) acrylate, 2- (octyloxycarbonyloxy) butyl (meth) acrylate Family (meth) acrylic acid esters;
例えば、(メタ)アクリル酸2−オキソブタノイルエチル、(メタ)アクリル酸2−オキソブタノイルプロピル、(メタ)アクリル酸2−オキソブタノイルブチル、(メタ)アクリル酸2−オキソブタノイルヘキシル、(メタ)アクリル酸2−オキソブタノイルオクチル、(メタ)アクリル酸2−オキソブタノイルデシル、(メタ)アクリル酸2−オキソブタノイルドデシル、(メタ)アクリル酸3−オキソブタノイルエチル、(メタ)アクリル酸3−オキソブタノイルプロピル、(メタ)アクリル酸3−オキソブタノイルブチル、(メタ)アクリル酸3−オキソブタノイルヘキシル、(メタ)アクリル酸3−オキソブタノイルオクチル、(メタ)アクリル酸3−オキソブタノイルデシル、(メタ)アクリル酸3−オキソブタノイルドデシル、(メタ)アクリル酸4−シアノオキソブタノイルエチル、(メタ)アクリル酸4−シアノオキソブタノイルプロピル、(メタ)アクリル酸4−シアノオキソブタノイルブチル、(メタ)アクリル酸4−シアノオキソブタノイルヘキシル、(メタ)アクリル酸4−シアノオキソブタノイルオクチル、(メタ)アクリル酸2,3−ジ(オキソブタノイル)プロピル、(メタ)アクリル酸2,3−ジ(オキソブタノイル)ブチル、(メタ)アクリル酸2,3−ジ(オキソブタノイル)ヘキシル、(メタ)アクリル酸2,3−ジ(オキソブタノイル)オクチル等のカルボニル基を2つ有する脂肪族系の(メタ)アクリル酸エステル類; For example, 2-oxobutanoylethyl (meth) acrylate, 2-oxobutanoylpropyl (meth) acrylate, 2-oxobutanoylbutyl (meth) acrylate, 2-oxobutanoylhexyl (meth) acrylate, (Meth) acrylate 2-oxobutanoyloctyl, (meth) acrylate 2-oxobutanoyldecyl, (meth) acrylate 2-oxobutanoyldodecyl, (meth) acrylate 3-oxobutanoylethyl, (meth) ) 3-oxobutanoylpropyl acrylate, 3-oxobutanoylbutyl (meth) acrylate, 3-oxobutanoylhexyl (meth) acrylate, 3-oxobutanoyloctyl (meth) acrylate, (meth) acrylic 3-oxobutanoyl decyl acid, 3-oxobutanoyl dodecyl (meth) acrylate, 4-cyanooxobutane (meth) acrylate Ylethyl, 4-cyanooxobutanoylpropyl (meth) acrylate, 4-cyanooxobutanoylbutyl (meth) acrylate, 4-cyanooxobutanoylhexyl (meth) acrylate, 4-cyanooxo (meth) acrylate Butanoyloctyl, 2,3-di (oxobutanoyl) propyl (meth) acrylate, 2,3-di (oxobutanoyl) butyl (meth) acrylate, 2,3-di (oxo) (meth) acrylate Aliphatic (meth) acrylic acid esters having two carbonyl groups such as butanoyl) hexyl and 2,3-di (oxobutanoyl) octyl (meth) acrylate;
例えば、(メタ)アクリル酸−9−メトキシカルボニル−5−オキソ−4−オキサ−トリシクロ[4.2.1.03,7]ノナ−2−イル、(メタ)アクリル酸−10−メトキシカルボニル−5−オキソ−4−オキサ−トリシクロ[5.2.1.03,8]ノナ−2−イル、(メタ)アクリル酸−4−メトキシカルボニル−6−オキソ−7−オキサ−ビシクロ[3.2.1]オクタ−2−イル、(メタ)アクリル酸−4−メトキシカルボニル−7−オキソ−8−オキサ−ビシクロ[3.3.1]オクタ−2−イル等のカルボニル基を有する(メタ)アクリル酸環状エステル類; For example, (meth) acrylic acid-9-methoxycarbonyl-5-oxo-4-oxa-tricyclo [4.2.1.0 3,7 ] non-2-yl, (meth) acrylic acid-10-methoxycarbonyl -5-oxo-4-oxa-tricyclo [5.2.1.0 3,8 ] non-2-yl, (meth) acrylic acid-4-methoxycarbonyl-6-oxo-7-oxa-bicyclo [3 2.1] having a carbonyl group such as octa-2-yl, (meth) acrylic acid-4-methoxycarbonyl-7-oxo-8-oxa-bicyclo [3.3.1] oct-2-yl ( (Meth) acrylic acid cyclic esters;
例えば、N−(2−オキソブタノイルエチル)(メタ)アクリルアミド、N−(2−オキソブタノイルプロピル)(メタ)アクリルアミド、N−(2−オキソブタノイルブチル)(メタ)アクリルアミド、N−(2−オキソブタノイルヘキシル)(メタ)アクリルアミド、N−(2−オキソブタノイルオクチル)(メタ)アクリルアミド、ダイアセトン(メタ)アクリルアミド等のカルボニル基を有する(メタ)アクリルアミド類; For example, N- (2-oxobutanoylethyl) (meth) acrylamide, N- (2-oxobutanoylpropyl) (meth) acrylamide, N- (2-oxobutanoylbutyl) (meth) acrylamide, N- ( (Meth) acrylamides having a carbonyl group such as 2-oxobutanoylhexyl) (meth) acrylamide, N- (2-oxobutanoyloctyl) (meth) acrylamide, diacetone (meth) acrylamide;
例えば、アセト酢酸ビニル、アセトプロピオン酸ビニル、アセトイソ酪酸ビニル、アセト酪酸ビニル、アセトバレリン酸ビニル、アセトヘキサン酸ビニル、アセト2−エチルヘキサン酸ビニル、アセトn−オクタン酸ビニル、アセトデカン酸ビニル、アセトドデカン酸ビニル、アセトオクタデカン酸ビニル、アセトピバリン酸ビニル、アセトカプリン酸ビニル、アセトクロトン酸ビニル、アセトソルビン酸ビニル、プロパノイル酢酸ビニル、ブチリル酢酸ビニル、イソブチリル酢酸ビニル、パルミトイル酢酸ビニル、ステアロイル酢酸ビニル、ピルボイル酢酸ビニル、プロパノイルバレリン酸ビニル、ブチリルバレリン酸ビニル、イソブチリルバレリン酸ビニル、パルミトイルバレリン酸ビニル、ステアロイルバレリン酸ビニル、ピルボイルバレリン酸ビニル、2−アセトアセトキシエチルビニルエーテル、2−アセトアセトキシブチルビニルエーテル、2−アセトアセトキシヘキシルビニルエーテル、2−アセトアセトキシオクチルビニルエーテル等のアシル基を有する脂肪族系のビニル化合物類; For example, vinyl acetoacetate, vinyl acetopropionate, vinyl acetoisobutyrate, vinyl acetobutyrate, vinyl acetovalerate, vinyl acetohexanoate, vinyl aceto-2-ethylhexanoate, vinyl aceto-n-octanoate, vinyl acetodecanoate, acetodecane Vinyl acid, vinyl acetooctadecanoate, vinyl acetopivalate, vinyl acetocaprate, vinyl acetocrotonate, vinyl acetosorbate, vinyl propanoyl acetate, vinyl butyryl acetate, vinyl isobutyryl acetate, vinyl palmitoyl acetate, vinyl stearoyl acetate, vinyl pyroyl acetate , Vinyl propanoyl valerate, vinyl butyryl valerate, vinyl isobutyryl valerate, palmitoyl vinyl valerate, stearoyl valerate, pyrvoyl Vinyl Rerin acid, 2-acetoacetoxyethyl vinyl ether, 2-acetoacetoxyethyl butyl vinyl ether, 2-acetoacetoxyethyl hexyl vinyl ether, aliphatic vinyl compounds of having an acyl group such as 2-acetoacetoxyethyl octyl vinyl ether;
例えば、ベンゾイル蟻酸ビニル、ベンゾイル酢酸ビニル、ベンゾイルプロピオン酸ビニル、ベンゾイル酪酸ビニル、ベンゾイルバレリン酸ビニル、ベンゾイルヘキサン酸ビニル、ベンゾイルドデカン酸ビニル、1−ナフトイル酢酸ビニル、1−ナフトイルプロピオン酸ビニル、1−ナフトイル酪酸ビニル、1−ナフトイルバレリン酸ビニル、1−ナフトイルヘキサン酸ビニル、2−ナフトイル酢酸ビニル、2−ナフトイルプロピオン酸ビニル、2−ナフトイル酪酸ビニル、2−ナフトイルバレリン酸ビニル、2−ナフトイルヘキサン酸ビニル、ニコチノイル酢酸ビニル、ニコチノイルプロピオン酸ビニル、ニコチノイル酪酸ビニル、ニコチノイルバレリン酸ビニル、ニコチノイルヘキサン酸ビニル、ニコチノイルデカン酸ビニル、ニコチノイルドデカン酸ビニル、イソニコチノイル酢酸ビニル、イソニコチノイルプロピオン酸ビニル、イソニコチノイル酪酸ビニル、イソニコチノイルバレリン酸ビニル、イソニコチノイルヘキサン酸ビニル、イソニコチノイルデカン酸ビニル、イソニコチノイルドデカン酸ビニル、2−フロイル酢酸ビニル、2−フロイルプロピオン酸ビニル、2−フロイル酪酸ビニル、2−フロイルバレリン酸ビニル、2−フロイルヘキサン酸ビニル、2−フロイルデカン酸ビニル、2−フロイルドデカン酸ビニル、3−フロイル酢酸ビニル、3−フロイルプロピオン酸ビニル、3−フロイル酪酸ビニル、3−フロイルバレリン酸ビニル、3−フロイルヘキサン酸ビニル、3−フロイルデカン酸ビニル、3−フロイルドデカン酸ビニル、アントラニロイル酢酸ビニル、アントラニロイルプロピオン酸ビニル、アントラニロイル酪酸ビニル、アントラニロイルバレリン酸ビニル、アントラニロイルヘキサン酸ビニル、アントラニロイルデカン酸ビニル、アントラニロイルドデカン酸ビニル、4−(2−t−エトキシカルボニルエチルオキシ)スチレン、4−(2−t−ブトキシカルボニルエチルオキシ)スチレン、4−(2−t−ブトキシカルボニルプロピルオキシ)スチレン等のアシル基を有する芳香族系のビニル化合物類; For example, vinyl benzoylformate, vinyl benzoyl acetate, vinyl benzoylpropionate, vinyl benzoylbutyrate, vinyl benzoylvalerate, vinyl benzoylhexanoate, vinyl benzoyldodecanoate, 1-naphthoylvinyl acetate, 1-naphthoylpropionate, 1- Naphthoyl vinyl butyrate, 1-naphthoyl vinyl valerate, 1-naphtho vinyl hexanoate, 2-naphtho vinyl acetate, 2-naphtho vinyl propionate, 2-naphtho vinyl butyrate, 2-naphtho vinyl butyrate, 2- Vinyl naphthoyl hexanoate, vinyl nicotinoyl acetate, vinyl nicotinoyl propionate, vinyl nicotinoyl butyrate, vinyl nicotinoyl valerate, vinyl nicotinoyl hexanoate, vinyl nicotinoyl decanoate, nicotine Vinyl dodecanoate, vinyl isonicotinoyl acetate, vinyl isonicotinoyl propionate, vinyl isonicotinoyl butyrate, vinyl isonicotinoyl valerate, vinyl isonicotinoyl hexanoate, vinyl isonicotinoyl decanoate, vinyl isonicotinoyl dodecanoate, 2-furoyl Vinyl acetate, vinyl 2-furoylpropionate, vinyl 2-furoylbutyrate, vinyl 2-furoylvalerate, vinyl 2-furoylhexanoate, vinyl 2-furoyldecanoate, vinyl 2-furoyldodecanoate, 3-furoyl Vinyl acetate, vinyl 3-furoylpropionate, vinyl 3-furoylbutyrate, vinyl 3-furoylvalerate, vinyl 3-furoylhexanoate, vinyl 3-furoyldecanoate, vinyl 3-furoyldodecanoate, vinyl anthraniloyl acetate , Vinyl anthraniloyl propionate, vinyl anthraniloyl butyrate, vinyl anthraniloyl valerate, vinyl anthraniloyl hexanoate, vinyl anthraniloyl decanoate, vinyl anthraniloyl decanoate, 4- (2-t-ethoxycarbonylethyl Aromatic vinyl compounds having an acyl group, such as oxy) styrene, 4- (2-t-butoxycarbonylethyloxy) styrene, 4- (2-t-butoxycarbonylpropyloxy) styrene;
例えば、アセト酢酸(メタ)アリル、アセトプロピオン酸(メタ)アリル、アセトイソ酪酸(メタ)アリル、アセト酪酸(メタ)アリル、アセトバレリン酸(メタ)アリル、アセトヘキサン酸(メタ)アリル、アセト2−エチルヘキサン酸(メタ)アリル、アセトn−オクタン酸(メタ)アリル、アセトデカン酸(メタ)アリル、アセトドデカン酸(メタ)アリル、アセトオクタデカン酸(メタ)アリル、アセトピバリン酸(メタ)アリル、アセトカプリン酸(メタ)アリル、アセトクロトン酸(メタ)アリル、アセトソルビン酸(メタ)アリル、プロパノイル酢酸(メタ)アリル、ブチリル酢酸(メタ)アリル、イソブチリル酢酸(メタ)アリル、パルミトイル酢酸(メタ)アリル、ステアロイル酢酸(メタ)アリル、(メタ)アリルアルデヒド等のアシル基を有する脂肪族系の(メタ)アリル化合物類; For example, acetoacetic acid (meth) allyl, acetopropionic acid (meth) allyl, acetoisobutyric acid (meth) allyl, acetobutyric acid (meth) allyl, acetovaleric acid (meth) allyl, acetohexanoic acid (meth) allyl, aceto-2- Ethylhexanoic acid (meth) allyl, aceto-n-octanoic acid (meth) allyl, acetodecanoic acid (meth) allyl, acetodecanoic acid (meth) allyl, acetooctadecanoic acid (meth) allyl, acetopivalic acid (meth) allyl, acetocaprin Acid (meth) allyl, acetocrotonic acid (meth) allyl, acetosorbic acid (meth) allyl, propanoyl acetate (meth) allyl, butyryl acetate (meth) allyl, isobutyryl acetate (meth) allyl, palmitoyl acetate (meth) allyl, Aliphatic (meth) allyl compounds having an acyl group such as stearoyl acetate (meth) allyl and (meth) allylaldehyde
例えば、ベンゾイル蟻酸(メタ)アリル、ベンゾイル酢酸(メタ)アリル、ベンゾイルプロピオン酸(メタ)アリル、ベンゾイル酪酸(メタ)アリル、ベンゾイルバレリン酸(メタ)アリル、ベンゾイルヘキサン酸(メタ)アリル、ベンゾイルドデカン酸(メタ)アリル、1−ナフトイル酢酸(メタ)アリル、1−ナフトイルプロピオン酸(メタ)アリル、1−ナフトイル酪酸(メタ)アリル、1−ナフトイルバレリン酸(メタ)アリル、1−ナフトイルヘキサン酸(メタ)アリル、2−ナフトイル酢酸(メタ)アリル、2−ナフトイルプロピオン酸(メタ)アリル、2−ナフトイル酪酸(メタ)アリル、2−ナフトイルバレリン酸(メタ)アリル、2−ナフトイルヘキサン酸(メタ)アリル等のアシル基を有する芳香族系の(メタ)アリル化合物類等のカルボニル基含有のα,β−不飽和二重結合基含有化合物類; For example, benzoyl formate (meth) allyl, benzoyl acetate (meth) allyl, benzoyl propionate (meth) allyl, benzoyl butyrate (meth) allyl, benzoylvalerate (meth) allyl, benzoylhexanoic acid (meth) allyl, benzoyldodecanoic acid (Meth) allyl, 1-naphthoylacetic acid (meth) allyl, 1-naphthoylpropionic acid (meth) allyl, 1-naphthoylbutyric acid (meth) allyl, 1-naphthoylvaleric acid (meth) allyl, 1-naphthoylhexane Acid (meth) allyl, 2-naphthoyl acetate (meth) allyl, 2-naphthoyl propionate (meth) allyl, 2-naphthoyl butyrate (meth) allyl, 2-naphthoylvalerate (meth) allyl, 2-naphthoyl Α, β-unsaturated double bonds containing carbonyl groups such as aromatic (meth) allyl compounds having acyl groups such as (meth) allyl hexanoate Compound containing compounds;
例えば、(メタ)アクリル酸アシッドホスホオキシエチル、(メタ)アクリル酸アシッドホスホオキシプロピル、(メタ)アクリル酸アシッドホスホオキシブチル、(メタ)アクリル酸−3−クロロ−2−アシッドホスホオキシエチル、(メタ)アクリル酸−3−クロロ−2−アシッドホスホオキシプロピル、(メタ)アクリル酸−3−クロロ−2−アシッドホスホオキシブチル等のホスホン酸基含有(メタ)アクリル酸エステル類; For example, (meth) acrylic acid phosphooxyethyl, (meth) acrylic acid phosphooxypropyl, (meth) acrylic acid phosphooxybutyl, (meth) acrylic acid-3-chloro-2-acid phosphooxyethyl, (Meth) acrylic acid esters containing phosphonic acid groups such as (meth) acrylic acid-3-chloro-2-acid phosphooxypropyl, (meth) acrylic acid-3-chloro-2-acid phosphooxybutyl;
例えば、3−(メタ)アクリロイルオキシプロピルメチルジメトキシシラン、3−(メタ)アクリロイルオキシプロピルトリメトキシシラン、3−(メタ)アクリロイルオキシプロピルトリプロポキシシラン、3−(メタ)アクリロイルオキシプロピルトリブトキシシシラン、3−(メタ)アクリロイルオキシプロピルメチルジメトキシシラン、3−(メタ)アクリロイルオキシプロピルメチルジエトキシシラン、3−(メタ)アクリロイルオキシプロピルエチルジメトキシシラン、3−(メタ)アクリロイルオキシプロピルブチルジメトキシシラン、3−(メタ)アクリロイルオキシプロピルエチルジプロポキシシラン、3−(メタ)アクリロイルオキシプロピルメチルジエトキシシラン、3−(メタ)アクリロイルオキシプロピルトリメトキシシラン、3−(メタ)アクリロイルオキシプロピルトリエトキシシラン、3−(メタ)アクリロイルオキシプロピルトリプロポキシシラン等のアルコキシシリル基含有(メタ)アクリル酸エステル類; For example, 3- (meth) acryloyloxypropylmethyldimethoxysilane, 3- (meth) acryloyloxypropyltrimethoxysilane, 3- (meth) acryloyloxypropyltripropoxysilane, 3- (meth) acryloyloxypropyltributoxysilane 3- (meth) acryloyloxypropylmethyldimethoxysilane, 3- (meth) acryloyloxypropylmethyldiethoxysilane, 3- (meth) acryloyloxypropylethyldimethoxysilane, 3- (meth) acryloyloxypropylbutyldimethoxysilane, 3- (meth) acryloyloxypropylethyl dipropoxysilane, 3- (meth) acryloyloxypropylmethyldiethoxysilane, 3- (meth) acryloyloxypropyltrimethoxysilane, 3- (meth) acrylic Yl trimethoxy silane, 3- (meth) acryloyloxy propyl trimethoxy propoxy alkoxysilyl group-containing (meth) acrylic acid esters such as silane;
例えば、(メタ)アクリロイルオキシジメチルエチルアンモニウムエチルサルフェート、(メタ)アクリロイルアミノプロピルトリメチルアンモニウムサルフェート、(メタ)アクリロイルアミノプロピルトリエチルアンモニウムサルフェート等のスルホニル基含有の(メタ)アクリル酸エステル類の金属塩やアンモニウム塩; For example, metal salts and ammonium of sulfonyl group-containing (meth) acrylic acid esters such as (meth) acryloyloxydimethylethylammonium ethyl sulfate, (meth) acryloylaminopropyltrimethylammonium sulfate, (meth) acryloylaminopropyltriethylammonium sulfate salt;
例えば、ジ(メタ)アクリル酸エチレンオキサイド、ジ(メタ)アクリル酸トリエチレンオキサイド、ジ(メタ)アクリル酸テトラエチレンオキサイド、ジ(メタ)アクリル酸ポリエチレンオキサイド、ジ(メタ)アクリル酸プロピレンオキサイド、ジ(メタ)アクリル酸ジプロピレンオキサイド、ジ(メタ)アクリル酸トリプロピレンオキサイド、ジ(メタ)アクリル酸ポリプロピレンオキサイド、ジ(メタ)アクリル酸ブテンオキサイド、ジ(メタ)アクリル酸ペンテンオキサイド、ジ(メタ)アクリル酸2,2−ジメチルプロピル、ジ(メタ)アクリル酸ヒドロキシピバリルヒドロキシピバレート、ジ(メタ)アクリル酸ヒドロキシピバリルヒドロキシピバレートジカプロラクトネート、ジ(メタ)アクリル酸1,6−ヘキサンジオール、ジ(メタ)アクリル酸1,2−ヘキサンジオール、ジ(メタ)アクリル酸1,5−ヘキサンジオール、ジ(メタ)アクリル酸2,5−ヘキサンジオール、ジ(メタ)アクリル酸1,7−ヘプタンジオール、ジ(メタ)アクリル酸1,8−オクタンジオール、ジ(メタ)アクリル酸1,2−オクタンジオール、ジ(メタ)アクリル酸1,9−ノナンジオール、ジ(メタ)アクリル酸1,2−デカンジオール、ジ(メタ)アクリル酸1,10−デカンジオール、ジ(メタ)アクリル酸1,2−デカンジオール、ジ(メタ)アクリル酸1,12−ドデカンジオール、ジ(メタ)アクリル酸1,2−ドデカンジオール、ジ(メタ)アクリル酸1,14−テトラデカンジオール、ジ(メタ)アクリル酸1,2−テトラデカンジオール、ジ(メタ)アクリル酸1,16−ヘキサデカンジオール、ジ(メタ)アクリル酸1,2−ヘキサデカンジオール、ジ(メタ)アクリル酸2−メチル−2,4−ペンタンジオール、ジ(メタ)アクリル酸3−メチル−1,5−ペンタンジオール、ジ(メタ)アクリル酸2−メチル−2-プロピル−1,3−プロパンジオール、ジ(メタ)アクリル酸2,4−ジメチル−2,4−ペンタンジオール、ジ(メタ)アクリル酸2,2−ジエチル−1,3−プロパンジオール、ジ(メタ)アクリル酸2,2,4−トリメチル-1,3-ペンタンジオール、ジ(メタ)アクリル酸ジメチロールオクタン、ジ(メタ)アクリル酸2−エチル−1,3−ヘキサンジオール、ジ(メタ)アクリル酸2,5−ジメチル−2,5−ヘキサンジオール、ジ(メタ)アクリル酸2-メチル−1,8−オクタンジオール、ジ(メタ)アクリル酸2−ブチル−2−エチル−1,3-プロパンジオール、ジ(メタ)アクリル酸2,4−ジエチル−1,5−ペンタンジオール、ジ(メタ)アクリル酸2−メチル−2-プロピル−1,3−プロパンジオール、ジ(メタ)アクリル酸2,4−ジメチル−2,4−ペンタンジオール、ジ(メタ)アクリル酸2,2−ジエチル−1,3−プロパンジオール、ジ(メタ)アクリル酸2,2,4−トリメチル−1,3−ペンタンジオール、ジ(メタ)アクリル酸ジメチロールオクタン、ジ(メタ)アクリル酸2−エチル−1,3−ヘキサンジオール、ジ(メタ)アクリル酸2,5−ジメチル−2,5−ヘキサンジオール、ジ(メタ)アクリル酸2−ブチル−2-エチル−1,3−プロパンジオール、ジ(メタ)アクリル酸2,4−ジエチル−1,5−ペンタンジオール、ジ(メタ)アクリル酸1,1,1−トリスヒドロキシメチルエタン等の2官能(メタ)アクリル酸エステル類; For example, di (meth) acrylic acid ethylene oxide, di (meth) acrylic acid triethylene oxide, di (meth) acrylic acid tetraethylene oxide, di (meth) acrylic acid polyethylene oxide, di (meth) acrylic acid propylene oxide, di (Meth) acrylic acid dipropylene oxide, di (meth) acrylic acid tripropylene oxide, di (meth) acrylic acid polypropylene oxide, di (meth) acrylic acid butene oxide, di (meth) acrylic acid pentane oxide, di (meth) 2,2-dimethylpropyl acrylate, hydroxypivalylhydroxypivalate di (meth) acrylate, hydroxypivalylhydroxypivalate hydroxypivalate dicaprolactonate, 1,6-hexane di (meth) acrylate Diol, di (meth) acrylic acid 1,2-hexane All, di (meth) acrylic acid 1,5-hexanediol, di (meth) acrylic acid 2,5-hexanediol, di (meth) acrylic acid 1,7-heptanediol, di (meth) acrylic acid 1,8 -Octanediol, di (meth) acrylic acid 1,2-octanediol, di (meth) acrylic acid 1,9-nonanediol, di (meth) acrylic acid 1,2-decanediol, di (meth) acrylic acid 1 , 10-decanediol, di (meth) acrylic acid 1,2-decanediol, di (meth) acrylic acid 1,12-dodecanediol, di (meth) acrylic acid 1,2-dodecanediol, di (meth) acrylic Acid 1,14-tetradecanediol, di (meth) acrylic acid 1,2-tetradecanediol, di (meth) acrylic acid 1,16-hexadecanediol, di (meth) acrylic acid 1,2-hexadecane All, di (meth) acrylate 2-methyl-2,4-pentanediol, di (meth) acrylate 3-methyl-1,5-pentanediol, di (meth) acrylate 2-methyl-2-propyl- 1,3-propanediol, 2,4-dimethyl-2,4-pentanediol di (meth) acrylate, 2,2-diethyl-1,3-propanediol di (meth) acrylate, di (meth) acryl Acid 2,2,4-trimethyl-1,3-pentanediol, dimethyloloctane di (meth) acrylate, 2-ethyl-1,3-hexanediol di (meth) acrylate, di (meth) acrylic acid 2 , 5-dimethyl-2,5-hexanediol, 2-methyl-1,8-octanediol di (meth) acrylate, 2-butyl-2-ethyl-1,3-propanediol di (meth) acrylate, Di (meth) acrylic 2,4-diethyl-1,5-pentanediol, 2-methyl-2-propyl-1,3-propanediol di (meth) acrylate, 2,4-dimethyl-2,4-di (meth) acrylate Pentanediol, 2,2-diethyl-1,3-propanediol di (meth) acrylate, 2,2,4-trimethyl-1,3-pentanediol di (meth) acrylate, di (meth) acrylate di Methyloloctane, 2-ethyl-1,3-hexanediol di (meth) acrylate, 2,5-dimethyl-2,5-hexanediol di (meth) acrylate, 2-butyl-2 di (meth) acrylate -Bifunctional such as ethyl-1,3-propanediol, 2,4-diethyl-1,5-pentanediol di (meth) acrylate, 1,1,1-trishydroxymethylethane di (meth) acrylate ( (Meta) Acry Esters;
例えば、トリ(メタ)アクリル酸1,2,3−プロパントリオール、トリ(メタ)アクリル酸2−メチルペンタン−2,4−ジオール、トリ(メタ)アクリル酸2−メチルペンタン−2,4−ジオールトリカプロラクトネート、トリ(メタ)アクリル酸2,2−ジメチルプロパン−1,3−ジオール、トリ(メタ)アクリル酸トリメチロールヘキサン、トリ(メタ)アクリル酸トリメチロールオクタン、トリ(メタ)アクリル酸2,2−ビス(ヒドロキシメチル)1,3−プロパンジオール、トリ(メタ)アクリル酸1,1,1−トリスヒドロキシメチルエタン、トリ(メタ)アクリル酸1,1,1−トリスヒドロキシメチルプロパン、トリ(メタ)アクリル酸ペンタエリスリトール等の3官能(メタ)アクリル酸エステル類; For example, 1,2,3-propanetriol tri (meth) acrylate, 2-methylpentane-2,4-diol tri (meth) acrylate, 2-methylpentane-2,4-diol tri (meth) acrylate Tricaprolactonate, 2,2-dimethylpropane-1,3-diol tri (meth) acrylate, trimethylolhexane tri (meth) acrylate, trimethyloloctane tri (meth) acrylate, tri (meth) acrylic acid 2,2-bis (hydroxymethyl) 1,3-propanediol, 1,1,1-trishydroxymethylethane tri (meth) acrylate, 1,1,1-trishydroxymethylpropane tri (meth) acrylate, Trifunctional (meth) acrylic esters such as pentaerythritol tri (meth) acrylate;
例えば、テトラ(メタ)アクリル酸ペンタエリスリトール、テトラ(メタ)アクリル酸エトキシ化ペンタエリスリトール、テトラ(メタ)アクリル酸ジトリメチロールプロパン、ヘキサ(メタ)アクリル酸ジペンタエリスリトール、テトラ(メタ)アクリル酸2,2−ビス(ヒドロキシメチル)1,3−プロパンジオール、テトラ(メタ)アクリル酸2,2−ビス(ヒドロキシメチル)1,3−プロパンジオールテトラカプロラクトネート、テトラ(メタ)アクリル酸ジ1,2,3−プロパントリオール、テトラ(メタ)アクリル酸ジ2−メチルペンタン−2,4−ジオール、テトラ(メタ)アクリル酸ジ2−メチルペンタン−2,4−ジオールテトラカプロラクトネート、テトラ(メタ)アクリル酸ジ2,2−ジメチルプロパン−1,3−ジオール、テトラ(メタ)アクリル酸ジトリメチロールブタン、テトラ(メタ)アクリル酸ジトリメチロールヘキサン、テトラ(メタ)アクリル酸ジトリメチロールオクタン等の多官能(メタ)アクリル酸エステル類; For example, tetra (meth) acrylate pentaerythritol, tetra (meth) acrylate ethoxylated pentaerythritol, tetra (meth) acrylate ditrimethylolpropane, hexa (meth) acrylate dipentaerythritol, tetra (meth) acrylate 2, 2-bis (hydroxymethyl) 1,3-propanediol, tetra (meth) acrylic acid 2,2-bis (hydroxymethyl) 1,3-propanediol tetracaprolactonate, tetra (meth) acrylic acid di1, 2,3-propanetriol, tetra (meth) acrylate di-2-methylpentane-2,4-diol, tetra (meth) acrylate di-2-methylpentane-2,4-diol tetracaprolactonate, Di, 2-dimethylpropane-1,3-diol, meth) acrylic acid, tetra (meth) acrylic acid Trimethylol butane, tetra (meth) polyfunctional (meth) acrylic esters of acrylic acid ditrimethylol hexane, tetra (meth) ditrimethylol octanoic acrylate;
例えば、ギ酸ビニル、酢酸ビニル、プロピオン酸ビニル、酪酸ビニル、カプリン酸ビニル、ラウリン酸ビニル、バーサチック酸ビニル、ピバリン酸ビニル、パルミチン酸ビニル、ステアリン酸ビニル等のカルボン酸のビニルエステル類; For example, vinyl esters of carboxylic acids such as vinyl formate, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl caprate, vinyl laurate, vinyl versatate, vinyl pivalate, vinyl palmitate, vinyl stearate;
例えば、メチルビニルエーテル、エチルビニルエーテル、2−クロロビニルエーテル、n−プロピルビニルエーテル、アリルビニルエーテル、イソプロピルビニルエーテル、n−ブチルビニルエーテル、イソブチルビニルエーテル、イソブチルビニルエーテル、tert−ブチルビニルエーテル、n−ペンチルビニルエーテル、イソペンチルビニルエーテル、tert−ペンチルビニルエーテル、n−ヘキシルビニルエーテル、イソヘキシルビニルエーテル、2−エチ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、n−ヘプチルビニルエーテル、n−オクチルビニルエーテル、イソオクチルビニルエーテル、ノニルビニルエーテル、デシルビニルエーテル、ドデシルビニルエーテル、ヘキサンデシルビニルエーテル、オクタデシルビニルエーテル、エトキシメチルビニルエーテル、2−メトキシエチルビニルエーテル、2−エトキシエチルビニルエーテル、2−ブトキシエチルビニルエーテル、アセトキシメチルビニルエーテル、2−アセトキシエチルビニルエーテル、3−アセトキシプロピルビニルエーテル、4−アセトキシブチルビニルエーテル、4−エトキシブチルビニルエーテル、2−(2−メトキシエトキシ)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、4−ヒドロキシブチルビニルエーテル、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などの脂肪族ビニルエーテル類; For example, methyl vinyl ether, ethyl vinyl ether, 2-chlorovinyl ether, n-propyl vinyl ether, allyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, isobutyl vinyl ether, tert-butyl vinyl ether, n-pentyl vinyl ether, isopentyl vinyl ether, tert -Pentyl vinyl ether, n-hexyl vinyl ether, isohexyl vinyl ether, 2-ethylbutyl vinyl ether, 2-ethylhexyl vinyl ether, n-heptyl vinyl ether, n-octyl vinyl ether, isooctyl vinyl ether, nonyl vinyl ether, decyl vinyl ether, dodecyl vinyl ether, hexanedecyl vinyl ether , Octa Sil vinyl ether, ethoxymethyl vinyl ether, 2-methoxyethyl vinyl ether, 2-ethoxyethyl vinyl ether, 2-butoxyethyl vinyl ether, acetoxymethyl vinyl ether, 2-acetoxyethyl vinyl ether, 3-acetoxypropyl vinyl ether, 4-acetoxybutyl vinyl ether, 4-ethoxy Aliphatic vinyl ethers such as butyl vinyl ether, 2- (2-methoxyethoxy) ethyl vinyl ether, 3-hydroxypropyl vinyl ether, 4-hydroxybutyl vinyl ether, 5-hydroxypentyl vinyl ether, 6-hydroxyhexyl vinyl ether;
例えば、エチ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(DEGVE)、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、プロピ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、ポリプロピレングリコールジビニルエーテル、ブタンジオールジビニルエーテル、ネオペンチルグリコールジビニルエーテル、ヘキサンジオールジビニルエーテル、ノナンジオールジビニルエーテル、ハイドロキノンジビニルエーテル、1,4−シクロヘキサンジオールジビニルエーテル(CHODVE)、1,4−シクロヘキサンジメタノールジビニルエーテル(CHDVE)、トリメチロールプロパントリビニルエーテル、ジペンタエリスリトールテトラビニルエーテル、ジトリメチロールプロパンテトラビニルエーテル、ジペンタエリスリトールヘキサビニルエーテル等の多官能のビニルエーテル類; For example, ethylene glycol divinyl ether, diethylene glycol divinyl ether (DEGVE), triethylene glycol divinyl ether, tetraethylene glycol divinyl ether, polyethylene glycol divinyl ether, propylene glycol divinyl ether, dipropylene glycol divinyl ether, tripropylene glycol divinyl ether, polypropylene glycol Divinyl ether, butanediol divinyl ether, neopentyl glycol divinyl ether, hexanediol divinyl ether, nonanediol divinyl ether, hydroquinone divinyl ether, 1,4-cyclohexanediol divinyl ether (CHODVE), 1,4-cyclohexanedimethanol divinyl ether ( CHD E), trimethylolpropane trivinyl ether, dipentaerythritol tetra ether, ditrimethylolpropane tetra vinyl ether, multifunctional, such as dipentaerythritol hexa ether;
例えば、パーフルオロビニル、パーフルオロプロペン、パーフルオロ(プロピルビニルエーテル)、フッ化ビニリデンなどのフッ素含有ビニル系化合物類; For example, fluorine-containing vinyl compounds such as perfluorovinyl, perfluoropropene, perfluoro (propyl vinyl ether), vinylidene fluoride;
例えば、(メタ)アリルクロロシラン、(メタ)アリルトリメトキシシラン、(メタ)アリルトリエトキシシラン、(メタ)アリルアミノトリメチルシラン、ジエトキシエチルビニルシラン、トリクロロビニルシラン、トリメトキシビニルシラン、トリエトキシビニルシラン、トリプロポキシビニルシラン、ビニルトリス(2−メトキシエトキシ)シラン等のアルコキシシリル基含有α,β−不飽和二重結合基含有化合物類; For example, (meth) allylchlorosilane, (meth) allyltrimethoxysilane, (meth) allyltriethoxysilane, (meth) allylaminotrimethylsilane, diethoxyethylvinylsilane, trichlorovinylsilane, trimethoxyvinylsilane, triethoxyvinylsilane, tripropoxy Alkoxysilyl group-containing α, β-unsaturated double bond group-containing compounds such as vinylsilane and vinyltris (2-methoxyethoxy) silane;
例えば、ビニルスルホン酸、2−プロペニルスルホン酸、2−メチル−2−プロペニルスルホン酸、ビニル硫酸等のアルケニル基含有スルホン酸類; For example, alkenyl group-containing sulfonic acids such as vinyl sulfonic acid, 2-propenyl sulfonic acid, 2-methyl-2-propenyl sulfonic acid, and vinyl sulfuric acid;
例えば、ビニルスルホン酸アンモニウム、ビニルスルホン酸ナトリウム、ビニルスルホン酸カリウム、ナトリウムビニルアルキルスルホサクシネート等の金属塩やアンモニウム塩類;
2−メチル−2−プロペニルスルホン酸アンモニウム、2−メチル−2−プロペニルスルホン酸ナトリウム、2−メチル−2−プロペニルスルホン酸カリウム等の2−メチル−2−プロペニルスルホン酸の金属塩やアンモニウム塩類;
For example, metal salts and ammonium salts such as ammonium vinyl sulfonate, sodium vinyl sulfonate, potassium vinyl sulfonate, sodium vinyl alkyl sulfosuccinate;
Metal salts and ammonium salts of 2-methyl-2-propenylsulfonic acid such as ammonium 2-methyl-2-propenylsulfonate, sodium 2-methyl-2-propenylsulfonate, and potassium 2-methyl-2-propenylsulfonate;
例えば、ジメチルアミノエチル(メタ)アクリルアミド、ジエチルアミノエチル(メタ)アクリルアミド、ジメチルアミノプロピル(メタ)アクリルアミド、ジエチルアミノプロピル(メタ)アクリルアミドなどのモノまたはジ-アルキルアミノアルキル(メタ)アクリルアミド類; For example, mono- or di-alkylaminoalkyl (meth) acrylamides such as dimethylaminoethyl (meth) acrylamide, diethylaminoethyl (meth) acrylamide, dimethylaminopropyl (meth) acrylamide, diethylaminopropyl (meth) acrylamide;
例えば、(メタ)アクリルアミド、N−メチル(メタ)アクリルアミド、N−エチル(メタ)アクリルアミド、N−プロピル(メタ)アクリルアミド、N−イソプロピル(メタ)アクリルアミド、N−ブチル(メタ)アクリルアミド、N−プロピル(メタ)アクリルアミド、N−tert−ブチル(メタ)アクリルアミド、N−ヘキシル(メタ)アクリルアミド、N−オクチル(メタ)アクリルアミド、N−ノニル(メタ)アクリルアミド、N−トリコシル(メタ)アクリルアミド、N−ノナデシル(メタ)アクリルアミド、N−ドコシル(メタ)アクリルアミド、N−メチレン(メタ)アクリルアミド、N−トリデシル(メタ)アクリルアミド、N−(5,5−ジメチルヘキシル)(メタ)アクリルアミド、クロトンアミド、マレインアミド、フマルアミド、メサコンアミド、シトラコンアミド、イタコンアミド、2−メチルプロパ−2−エノイルアミン、N,N−ジメチル(メタ)アクリルアミド、N,N−ジエチル−(メタ)アクリルアミド、N−[3−(N’,N’−ジメチルアミノ)プロピル]−(メタ)アクリルアミド、N−(ジブチルアミノメチル)(メタ)アクリルアミド、N−ビニルメタンアミド、N−ビニルアセトアミドなどの脂肪族系の(メタ)アクリルアミド類; For example, (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-butyl (meth) acrylamide, N-propyl (Meth) acrylamide, N-tert-butyl (meth) acrylamide, N-hexyl (meth) acrylamide, N-octyl (meth) acrylamide, N-nonyl (meth) acrylamide, N-tricosyl (meth) acrylamide, N-nonadecyl (Meth) acrylamide, N-docosyl (meth) acrylamide, N-methylene (meth) acrylamide, N-tridecyl (meth) acrylamide, N- (5,5-dimethylhexyl) (meth) acrylamide, crotonamide, maleinamide, Fumaramide, Mesaconamide, Citraconami , Itaconamide, 2-methylprop-2-enoylamine, N, N-dimethyl (meth) acrylamide, N, N-diethyl- (meth) acrylamide, N- [3- (N ′, N′-dimethylamino) propyl] -Aliphatic (meth) acrylamides such as (meth) acrylamide, N- (dibutylaminomethyl) (meth) acrylamide, N-vinylmethanamide, N-vinylacetamide;
例えば、N−メトキシメチル(メタ)アクリルアミド、N−メトキシエチル(メタ)アクリルアミド、N−メトキシプロピル(メタ)アクリルアミド、N−メトキシブチル(メタ)アクリルアミド、N−メトキシヘキシル(メタ)アクリルアミド、N−メトキシオクチル(メタ)アクリルアミド、N−メトキシデシル(メタ)アクリルアミド、N−メトキシドデシル(メタ)アクリルアミド、N−メトキシオクタデシル(メタ)アクリルアミド、N−エトキシメチル(メタ)アクリルアミド、N−エトキシエチル(メタ)アクリルアミド、N−エトキシプロピル(メタ)アクリルアミド、N−エトキシブチル(メタ)アクリルアミド、N−エトキシヘキシル(メタ)アクリルアミド、N−エトキシオクチル(メタ)アクリルアミド、N−イソプロポキシメチル(メタ)アクリルアミド、N−イソプロポキシエチル(メタ)アクリルアミド、N−イソプロポキシプロピル(メタ)アクリルアミド、N−イソプロポキシブチル(メタ)アクリルアミド、N−イソプロポキシヘキシル(メタ)アクリルアミド、N−イソプロポキシオクチル(メタ)アクリルアミド、N−ブトキシメチル(メタ)アクリルアミド、N−ブトキシエチル(メタ)アクリルアミド、N−ブトキシプロピル(メタ)アクリルアミド、N−ブトキシブチル(メタ)アクリルアミド、N−ブトキシヘキシル(メタ)アクリルアミド、N−ブトキシオクチル(メタ)アクリルアミド、N−イソブトキシメチル(メタ)アクリルアミド、N−イソブトキシエチル(メタ)アクリルアミド、N−イソブトキシプロピル(メタ)アクリルアミド、N−イソブトキシブチル(メタ)アクリルアミド、N−イソブトキシヘキシル(メタ)アクリルアミド、N−イソブトキシオクチル(メタ)アクリルアミド、N−(ペントキシメチル)(メタ)アクリルアミド、N−1−メチル−2−メトキシエチル(メタ)アクリルアミド、N,N−ジ(メトキシメチル)メタ)アクリルアミド、N,N−ジ(エトキシメチル)(メタ)アクリルアミド等のN−アルコキシ基含有の(メタ)アクリルアミド類; For example, N-methoxymethyl (meth) acrylamide, N-methoxyethyl (meth) acrylamide, N-methoxypropyl (meth) acrylamide, N-methoxybutyl (meth) acrylamide, N-methoxyhexyl (meth) acrylamide, N-methoxy Octyl (meth) acrylamide, N-methoxydecyl (meth) acrylamide, N-methoxydodecyl (meth) acrylamide, N-methoxyoctadecyl (meth) acrylamide, N-ethoxymethyl (meth) acrylamide, N-ethoxyethyl (meth) acrylamide N-ethoxypropyl (meth) acrylamide, N-ethoxybutyl (meth) acrylamide, N-ethoxyhexyl (meth) acrylamide, N-ethoxyoctyl (meth) acrylamide, N-isopropoxymethyl (meth) acrylamide, N Isopropoxyethyl (meth) acrylamide, N-isopropoxypropyl (meth) acrylamide, N-isopropoxybutyl (meth) acrylamide, N-isopropoxyhexyl (meth) acrylamide, N-isopropoxyoctyl (meth) acrylamide, N- Butoxymethyl (meth) acrylamide, N-butoxyethyl (meth) acrylamide, N-butoxypropyl (meth) acrylamide, N-butoxybutyl (meth) acrylamide, N-butoxyhexyl (meth) acrylamide, N-butoxyoctyl (meth) Acrylamide, N-isobutoxymethyl (meth) acrylamide, N-isobutoxyethyl (meth) acrylamide, N-isobutoxypropyl (meth) acrylamide, N-isobutoxybutyl (meth) acrylamide, N-isobutoxyhex Sil (meth) acrylamide, N-isobutoxyoctyl (meth) acrylamide, N- (pentoxymethyl) (meth) acrylamide, N-1-methyl-2-methoxyethyl (meth) acrylamide, N, N-di (methoxy) N-alkoxy group-containing (meth) acrylamides such as methyl) meth) acrylamide and N, N-di (ethoxymethyl) (meth) acrylamide;
例えば、(メタ)アクリルアミドスルホン酸、tert−ブチル−(メタ)アクリルアミドスルホン酸、(メタ)アクリルアミド−2−メチル−1−プロパンスルホン酸等のスルホン酸含有の(メタ)アクリルアミド類;
例えば、(メタ)アクリロニトリル、α−クロロアクリロニトリル、クロトンニトリル、マレインニトリル、フマロニトリル、メサコンニトリル、シトラコンニトリル、イタコンニトリル、2−プロペンニトリル、(メタ)アクリル酸2−シアノエチルなどのニトリル基含有α,β−不飽和二重結合基含有化合物類;
For example, (meth) acrylamides containing sulfonic acids such as (meth) acrylamide sulfonic acid, tert-butyl- (meth) acrylamide sulfonic acid, (meth) acrylamide-2-methyl-1-propanesulfonic acid;
For example, nitrile group-containing α, such as (meth) acrylonitrile, α-chloroacrylonitrile, crotonnitrile, maleinonitrile, fumaronitrile, mesaconnitrile, citraconnitrile, itaconnitrile, 2-propenenitrile, 2-methacrylic acid (meth) acrylate, β-unsaturated double bond group-containing compounds;
例えば、酢酸(メタ)アリル、プロピオン酸(メタ)アリル、酪酸(メタ)アリル、カプリン酸(メタ)アリル、ラウリン酸(メタ)アリル、オクチル酸アリル、ヤシ油脂肪酸、ピバリン酸ビニル等の飽和カルボン酸の(メタ)アリルエステル類; For example, saturated carboxylic acids such as (meth) allyl acetate, (meth) allyl propionate, (meth) allyl butyrate, (meth) allyl caprate, (meth) allyl laurate, allyl octylate, coconut oil fatty acid, vinyl pivalate, etc. (Meth) allyl esters of acids;
例えば、塩化ビニル、塩化ビニリデン、アリルクロライド等のハロゲン化ビニル類; For example, vinyl halides such as vinyl chloride, vinylidene chloride and allyl chloride;
例えば、アレン、1,2−ブタジエン、1,3−ブタジエン、2−メチル−1,3−ブタジエン、2−クロロ−1,3−ブタジエンなどのジエン類; For example, dienes such as allene, 1,2-butadiene, 1,3-butadiene, 2-methyl-1,3-butadiene, 2-chloro-1,3-butadiene;
例えば、cis−コハク酸ジアリル、2−メチリデンコハク酸ジアリル、(E)−ブタ−2−エン酸ビニル、(Z)−オクタデカ−9−エン酸ビニル、(9Z,12Z,15Z)−オクタデカ−9,12,15−トリエン酸ビニル等の多官能の不飽和結合を含有するα,β−不飽和二重結合基含有化合物類; For example, cis-diallyl succinate, diallyl 2-methylidene succinate, vinyl (E) -but-2-enoate, vinyl (Z) -octadeca-9-enoate, (9Z, 12Z, 15Z) -octadeca-9, Α, β-unsaturated double bond group-containing compounds containing polyfunctional unsaturated bonds such as vinyl 12,15-trienoate;
例えば、エチレン、プロピレン、1−ブテン、2−ブテン、2−メチルプロペン、1−ヘキセン、1−オクテン、1−デセン、1−ドデセン、1−テトラデセン、1−ヘキサデセン、1−オクタデセン、1−エイコセン、1−ドコセン、1−テトラコセン、1−ヘキサコセン、1−オクタコセン、1−トリアコンテン、1−ドトリアコンテン、1−テトラトアコンテン、1−ヘキサトリアコンテン、1−オクタトリアコンテン、1−テトラコンテン等ならびにその混合物やポリブテン−1,ポリペンテン−1,ポリ4−メチルペンテン−1等などのアルケン類; For example, ethylene, propylene, 1-butene, 2-butene, 2-methylpropene, 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene 1-docosene, 1-tetracocene, 1-hexacocene, 1-octacocene, 1-triacontene, 1-dotriacontene, 1-tetratoacontene, 1-hexatriacontene, 1-octatriacontene, 1-tetraconten And alkenes such as polybutene-1, polypentene-1, poly-4-methylpentene-1, etc .;
例えば、(メタ)アクリル酸、(メタ)アクリル酸2−カルボキシエチル、(メタ)アクリル酸2−カルボキシプロピル、(メタ)アクリル酸3−カルボキシプロピル、(メタ)アクリル酸4−カルボキシブチル、(メタ)アクリル酸ダイマー、マレイン酸、フマル酸、モノメチルマレイン酸、モノメチルフマル酸、アコニチン酸、ソルビン酸、ケイ皮酸、α−クロロソルビン酸、グルタコン酸、シトラコン酸、メサコン酸、イタコン酸、チグリン酸、アンゲリカ酸、セネシオ酸、クロトン酸、イソククロトン酸、ムコブロム酸、ムコクロル酸、ソルビン酸、ムコン酸、アコニット酸、ペニシル酸、ゲラン酸、シトロネル酸、4−アクリルアミドブタン酸、6−アクリルアミドヘキサン酸、2−(メタ)アクリロイルオキシエチルサクシネート、モノ(メタ)アクリル酸ω−カルボキシポリカプロラクトンエステル等の、ラクトン環の開環付加によるカルボキシル基を末端に有する、ポリラクトン系(メタ)アクリル酸エステル、エチレンオキサイドやプロピレンオキサイド等のアルキレンオキサイドが繰り返し付加している、末端にカルボキシル基を有するアルキレンオキサイド付加系コハク酸と、(メタ)アクリル酸とのエステル等のカルボキシル基含有の脂肪族系α,β−不飽和二重結合基含有カルボン酸類やその酸無水物類; For example, (meth) acrylic acid, 2-carboxyethyl (meth) acrylate, 2-carboxypropyl (meth) acrylate, 3-carboxypropyl (meth) acrylate, 4-carboxybutyl (meth) acrylate, (meth ) Acrylic acid dimer, maleic acid, fumaric acid, monomethyl maleic acid, monomethyl fumaric acid, aconitic acid, sorbic acid, cinnamic acid, α-chlorosorbic acid, glutaconic acid, citraconic acid, mesaconic acid, itaconic acid, tiglic acid, Angelic acid, senetic acid, crotonic acid, isococrotonic acid, mucobromic acid, mucochloric acid, sorbic acid, muconic acid, aconitic acid, penicillic acid, gellanic acid, citronellic acid, 4-acrylamidobutanoic acid, 6-acrylamidohexanoic acid, 2- (Meth) acryloyloxyethyl succine , Mono (meth) acrylic acid ω-carboxy polycaprolactone ester, etc., repeating polylactone-based (meth) acrylic acid ester, ethylene oxide, propylene oxide and other alkylene oxides having a carboxyl group at the terminal by ring-opening addition of a lactone ring A carboxyl group-containing aliphatic α, β-unsaturated double bond group-containing carboxylic acid such as an ester of an alkylene oxide-added succinic acid having a carboxyl group at the terminal and (meth) acrylic acid, Its acid anhydrides;
例えば、2−(メタ)アクリロイルオキシエチルヘキサヒドロフタレート、2−(メタ)アクリロイルオキシエチルフタレート、2−(メタ)アクリロイルオキシプロピルフタレート、2−(メタ)アクリロイルオキシブチルフタレート、2−(メタ)アクリロイルオキシヘキシルフタレート、2−(メタ)アクリロイルオキシオクチルフタレート、2−(メタ)アクリロイルオキシデシルフタレート、2−ビニル安息香酸、3−ビニル安息香酸、4−ビニル安息香酸、4−イソプロペニルベンゼンカルボン酸、桂皮酸、7−アミノ−3−ビニル−3−セフェム−4−カルボン酸等のカルボキシル基含有の脂環や芳香環を有するα,β−不飽和二重結合基含有カルボン酸類やその酸無水物類; For example, 2- (meth) acryloyloxyethyl hexahydrophthalate, 2- (meth) acryloyloxyethyl phthalate, 2- (meth) acryloyloxypropyl phthalate, 2- (meth) acryloyloxybutyl phthalate, 2- (meth) acryloyl Oxyhexyl phthalate, 2- (meth) acryloyloxyoctyl phthalate, 2- (meth) acryloyloxydecyl phthalate, 2-vinylbenzoic acid, 3-vinylbenzoic acid, 4-vinylbenzoic acid, 4-isopropenylbenzenecarboxylic acid, Carboxylic acids such as cinnamic acid, 7-amino-3-vinyl-3-cephem-4-carboxylic acid and the like, and carboxylic acids containing alicyclic and aromatic rings containing aromatic groups and aromatic rings, and acid anhydrides thereof Kind;
例えば、(メタ)アクリル酸N−メチルアミノエチル、(メタ)アクリル酸N−エチルアミノエチル、(メタ)アクリル酸N−プロピルアミノエチル、(メタ)アクリル酸N−ブチルアミノエチル、(メタ)アクリル酸N−トリブチルアミノエチル、(メタ)アクリル酸テトラメチルピペリジニル、テトラメチルピペリジニルアクリレート等の1級、および/または2級のアミノ基を有する(メタ)アクリル酸エステル類; For example, N-methylaminoethyl (meth) acrylate, N-ethylaminoethyl (meth) acrylate, N-propylaminoethyl (meth) acrylate, N-butylaminoethyl (meth) acrylate, (meth) acryl (Meth) acrylic acid esters having primary and / or secondary amino groups such as acid N-tributylaminoethyl, tetramethylpiperidinyl (meth) acrylate, tetramethylpiperidinyl acrylate, etc .;
例えば、(メタ)アクリル酸ヒドラジド、2−(2−フリル)−3−(5−ニトロ−2−フリル)(メタ)アクリル酸ヒドラジド、β−(2−フラニル)(メタ)アクリル酸N2,N2−ビス(2−クロロエチル)ヒドラジド、p−ビニルベンズヒドラジド、N‐(m‐ビニルフェニル)アクリロヒドラジド、4−ビニルベンゼンスルホン酸ヒドラジド、2−[2−(5−ニトロ−2−フリル)ビニル]−4−-キノリンカルボヒドラジド等のヒドラジノ基を有する(メタ)アクリル酸エステル類; For example, (meth) acrylic acid hydrazide, 2- (2-furyl) -3- (5-nitro-2-furyl) (meth) acrylic acid hydrazide, β- (2-furanyl) (meth) acrylic acid N2, N2 -Bis (2-chloroethyl) hydrazide, p-vinylbenzhydrazide, N- (m-vinylphenyl) acrylohydrazide, 4-vinylbenzenesulfonic acid hydrazide, 2- [2- (5-nitro-2-furyl) vinyl ] -4- (Meth) acrylic acid esters having a hydrazino group such as quinolinecarbohydrazide;
例えば、(メタ)アクリル酸ジメチルアミノエチル、(メタ)アクリル酸ジエチルアミノエチル、(メタ)アクリル酸ジメチルアミノプロピル、(メタ)アクリル酸ジエチルアミノプロピル、ペンタメチルピペリジニル(メタ)アクリレート、4−(ピリミジン−2−イル)ピペラジン−1−イル(メタ)アクリレート等の3級アミノ基を有する(メタ)アクリル酸エステル類; For example, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, diethylaminopropyl (meth) acrylate, pentamethylpiperidinyl (meth) acrylate, 4- (pyrimidine (2-yl) piperazin-1-yl (meth) acrylate (meth) acrylic acid esters having a tertiary amino group;
例えば、モノメチルアミノエチル(メタ)アクリルアミド、モノエチルアミノエチル(メタ)アクリルアミド、モノメチルアミノプロピル(メタ)アクリルアミド、モノエチルアミノプロピル(メタ)アクリルアミド等の1級、および/または2級のアミノ基を有する(メタ)アクリルアミド類; For example, it has primary and / or secondary amino groups such as monomethylaminoethyl (meth) acrylamide, monoethylaminoethyl (meth) acrylamide, monomethylaminopropyl (meth) acrylamide, monoethylaminopropyl (meth) acrylamide, etc. (Meth) acrylamides;
例えば、ジメチルアミノエチル(メタ)アクリルアミド、ジエチルアミノエチル(メタ)アクリルアミド、ジメチルアミノプロピル(メタ)アクリルアミド、ジエチルアミノプロピル(メタ)アクリルアミドなどの3級のアミノ基を有する(メタ)アクリルアミド類; For example, (meth) acrylamides having a tertiary amino group such as dimethylaminoethyl (meth) acrylamide, diethylaminoethyl (meth) acrylamide, dimethylaminopropyl (meth) acrylamide, diethylaminopropyl (meth) acrylamide;
例えば、ビニルアミン、メチルビニルアミン、エチルビニルアミン、プロピルビニルアミン、ブチルビニルアミン、2−ビニルイミダゾール、2−ビニルピペラジン、4−ビニルピペラジン、2−ビニルピリジン、3−ビニルピリジン、4−ビニルピリジン、6−メチル−2−エテニルピリジン、2−ビニルピロール、2−メチル−5−ビニル−1H−ピロール、2−ビニルピラジン、2−メチル−5−ビニルピラジン、2−メチル−6−ビニルピラジン、2,5−ジメチル−3−ビニルピラジン、2−ビニルピリミジン、2−ビニルピリダジン、2−ビニル−1H−ベンゾイミダゾール、2−ビニル−5,6−ジメチル−1H−ベンゾイミダゾール、2−ビニルインダゾール、2−ビニルキノリン、4−ビニルキノリン、2−ビニルイソキノリン、2−ビニルイソキサリン、2−ビニルキノキサリン、2−ビニルキナゾリン、2−ビニルシンノリン、2,3−ジビニルピリジン、2,4−ジビニルピリジン、2,5−ジビニルピリジン、2,6−ジビニルピリジン等の1級、および/または2級のアミノ基を有するビニル化合物類; For example, vinylamine, methylvinylamine, ethylvinylamine, propylvinylamine, butylvinylamine, 2-vinylimidazole, 2-vinylpiperazine, 4-vinylpiperazine, 2-vinylpyridine, 3-vinylpyridine, 4-vinylpyridine, 6-methyl-2-ethenylpyridine, 2-vinylpyrrole, 2-methyl-5-vinyl-1H-pyrrole, 2-vinylpyrazine, 2-methyl-5-vinylpyrazine, 2-methyl-6-vinylpyrazine, 2,5-dimethyl-3-vinylpyrazine, 2-vinylpyrimidine, 2-vinylpyridazine, 2-vinyl-1H-benzimidazole, 2-vinyl-5,6-dimethyl-1H-benzimidazole, 2-vinylindazole, 2-vinylquinoline, 4-vinylquinoline, 2-vinylisoquino Phosphorus, 2-vinylisoxaline, 2-vinylquinoxaline, 2-vinylquinazoline, 2-vinylcinnoline, 2,3-divinylpyridine, 2,4-divinylpyridine, 2,5-divinylpyridine, 2,6- Vinyl compounds having primary and / or secondary amino groups such as divinylpyridine;
例えば、(メタ)アリルアミン、4−(メタ)アリル−3,5−ジメチル−1H−ピラゾール、5−(1−メチルプロピル)−5−(メタ)アリルピリミジン、5−(メタ)アリル−5−イソプロピルピリミジン、2−(メタ)アリルピリジン、4−(メタ)アリルピリジン、3,6−ジヒドロ−4−(メタ)アリルピリジン等の1級、および/または2級のアミノ基を有する(メタ)アリル化合物類; For example, (meth) allylamine, 4- (meth) allyl-3,5-dimethyl-1H-pyrazole, 5- (1-methylpropyl) -5- (meth) allylpyrimidine, 5- (meth) allyl-5- (Meth) having primary and / or secondary amino groups such as isopropylpyrimidine, 2- (meth) allylpyridine, 4- (meth) allylpyridine, 3,6-dihydro-4- (meth) allylpyridine, etc. Allyl compounds;
例えば、N−エチル−N−ニトロソビニルアミン等の3級アミノ基含有のビニル系化合物類; For example, vinyl compounds containing tertiary amino groups such as N-ethyl-N-nitrosovinylamine;
例えば、マレイミド、メチルマレイミド、エチルマレイミド、プロピルマレイミド、ブチルマレイミド、オクチルマレイミド、ドデシルマレイミド、ステアリルマレイミド、フェニルマレイミド、シクロヘキシルマレイミドなどの窒素原子と酸素原子の双方を有するマレイミド誘導体類のヘテロ環状のα,β−不飽和二重結合基含有化合物類等が挙げられるが、特にこれらに限定されるものではない。これらは、1種だけを用いてもよいし、あるいは、複数種を併用してもよい。 For example, heterocyclic α, maleimide derivatives having both nitrogen and oxygen atoms, such as maleimide, methylmaleimide, ethylmaleimide, propylmaleimide, butylmaleimide, octylmaleimide, dodecylmaleimide, stearylmaleimide, phenylmaleimide, cyclohexylmaleimide, etc. Examples include β-unsaturated double bond group-containing compounds, but are not particularly limited thereto. These may use only 1 type or may use multiple types together.
上記、その他のα,β−エチレン性不飽和二重結合基含有化合物(b3)として、反応性の観点から(メタ)アクリロイル基を有する化合物が好ましく、本発明の樹脂組成物を光立体造形材料として用いた場合、活性エネルギー線重合速度の観点から、2官能以上の(メタ)アクリル酸エステル類を含むことが、好ましい。 As said other (alpha), (beta) -ethylenically unsaturated double bond group containing compound (b3), the compound which has a (meth) acryloyl group from a reactive viewpoint is preferable, and the resin composition of this invention is optical stereolithography material When used as, it is preferable that bifunctional or higher (meth) acrylic acid esters are included from the viewpoint of the active energy ray polymerization rate.
<カチオン重合性化合物(C)>
本発明の重合性組成物の一実施形態において、重合性組成物は、カチオン重合性化合物(C) (以下「化合物(C)」と略記することがある)を含んでもよい。
<Cationically polymerizable compound (C)>
In one embodiment of the polymerizable composition of the present invention, the polymerizable composition may contain a cationically polymerizable compound (C) (hereinafter sometimes abbreviated as “compound (C)”).
化合物(C)は、酸触媒によりカチオン重合する官能基を1種以上含み、これらを特に制限なく使用することができる。化合物(C)としては活性エネルギー線による反応性の観点から、環状ヘテロ化合物(c)が好ましく、環状ヘテロ化合物のうち、環状エーテル基を1つ以上有する化合物が特に好ましく用いられる。 Compound (C) contains one or more functional groups that are cationically polymerized by an acid catalyst, and these can be used without any particular limitation. The compound (C) is preferably a cyclic hetero compound (c) from the viewpoint of reactivity by active energy rays, and a compound having one or more cyclic ether groups is particularly preferably used among the cyclic hetero compounds.
環状ヘテロ化合物(c)のうち、3員環状エーテル基を有する環状ヘテロ化合物であるエポキシ基含有化合物(c1)、4員環エーテルであるオキセタニル基含有化合物(c2)や5員環以上の環状エーテル化合物(c3)、2個以上の酸素又は酸素以外のヘテロ基を有する化合物(c4)がある。 Among the cyclic hetero compounds (c), an epoxy group-containing compound (c1) which is a cyclic hetero compound having a three-membered cyclic ether group, an oxetanyl group-containing compound (c2) which is a four-membered cyclic ether, and a cyclic ether having five or more members. There exists a compound (c4) which has a hetero group other than a compound (c3) 2 or more oxygen or oxygen.
[3員環状エーテル基を有する環状ヘテロ化合物であるエポキシ基含有化合物(c1)]
エポキシ基含有化合物(c1)としては、例えば、オキシラン、メチルオキシラン、フェニルオキシラン、1,2−ジフェニルオキシラン、メチリデンオキシラン、オキシラニルメチル、オキシラニルメタノール、オキシランカルボン酸、(クロロメチル)オキシラン、(ブロモメチル)オキシラン、オキシラニルアセトニトリル、2,2'−(ジメチルメチレン)ビス[(p−フェニレン)オキシメチレン]ビスオキシラン、2,2'−[メチレンビス(2,1−フェニレンオキシメチレン)]ビスオキシラン等のオキシラン化合物類、あるいは、グリシジルエーテル、グリシジルエステル、グリシジルアミン等のオキシラン環の水素原子がメチレン結合基やメチン結合基が置換されているエポキシ基含有化合物類;
[Epoxy group-containing compound (c1) which is a cyclic hetero compound having a 3-membered cyclic ether group]
Examples of the epoxy group-containing compound (c1) include oxirane, methyloxirane, phenyloxirane, 1,2-diphenyloxirane, methylideneoxirane, oxiranylmethyl, oxiranylmethanol, oxiranecarboxylic acid, (chloromethyl) oxirane. , (Bromomethyl) oxirane, oxiranylacetonitrile, 2,2 ′-(dimethylmethylene) bis [(p-phenylene) oxymethylene] bisoxirane, 2,2 ′-[methylenebis (2,1-phenyleneoxymethylene)] Oxirane compounds such as bisoxirane, or epoxy group-containing compounds in which a hydrogen atom of an oxirane ring such as glycidyl ether, glycidyl ester or glycidylamine is substituted with a methylene bond group or a methine bond group;
例えば、2−(シクロヘキシルメチル)オキシラン、2−エトキシ−3−(シクロヘキシルメチル)オキシラン等のシクロアルカン環を有するエポキシ基含有化合物類; For example, epoxy group-containing compounds having a cycloalkane ring such as 2- (cyclohexylmethyl) oxirane and 2-ethoxy-3- (cyclohexylmethyl) oxirane;
例えば、7−オキサビシクロ[4.1.0]ヘプタン、3−メチル−7−オキサビシクロ[4.1.0]ヘプタン等の芳香環を有しない脂環族系エポキシ基含有化合物類; For example, alicyclic epoxy group-containing compounds having no aromatic ring such as 7-oxabicyclo [4.1.0] heptane and 3-methyl-7-oxabicyclo [4.1.0] heptane;
例えば、3−フェニル−7−オキサビシクロ[4.1.0]ヘプタン−3−カルボキシレート、4−エチルフェニル7−オキサビシクロ[4.1.0]ヘプタン等の芳香環を有する脂環族系エポキシ基含有化合物類等が挙げられる。 For example, an alicyclic system having an aromatic ring such as 3-phenyl-7-oxabicyclo [4.1.0] heptane-3-carboxylate, 4-ethylphenyl 7-oxabicyclo [4.1.0] heptane Examples thereof include epoxy group-containing compounds.
[4員環エーテルであるオキセタニル基含有化合物(c2)]
オキセタニル基含有化合物(c2)としては、例えば、3−エチル−3−ヒドロキシメチルオキセタン、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、ジ(1−エチル−3−オキセタニル)メチルエーテル等が挙げられる。
[Oxetanyl group-containing compound which is a 4-membered ring ether (c2)]
Examples of the oxetanyl group-containing compound (c2) include 3-ethyl-3-hydroxymethyloxetane, 1,4-bis [(3-ethyl-3-oxetanyl) methoxymethyl] benzene, di (1-ethyl-3- Oxetanyl) methyl ether and the like.
[5員環以上の環状エーテル化合物(c3)]
5員環以上の環状エーテル化合物(c3)としては、例えば、2−メチルテトラヒドロフラン、2,5−ジエトキシテトラヒドロフラン、テトラヒドロフラン−2,2−ジメタノール3−メチル−2,4(3H、5H)−フランジオン等が挙げられる。
[Cyclic ether compound having 5 or more members (c3)]
Examples of the cyclic ether compound (c3) having 5 or more members include 2-methyltetrahydrofuran, 2,5-diethoxytetrahydrofuran, tetrahydrofuran-2,2-dimethanol 3-methyl-2,4 (3H, 5H)- Flange-on etc. are mentioned.
[2個以上の酸素又は酸素以外のヘテロ基を有する化合物(c4)]
2個以上の酸素又は酸素以外のヘテロ基を有する化合物(c4)としては、環状エステル化合物、環状ホルマール化合物、環状カーボネート化合物、含フッ素環状化合物等がある。環状ホルマール化合物が、ジオキソラン類、ジオキサン類及びトリオキサン類から選択される化合物であることが好ましい。
工業的には、プロピオラクトン、カプロラクトン、1,3−ジオキソラン、1,2−ジオキサン、1,4−ジオキサン、エチレンカーボネート、プロピレンカーボネート、グリセリンカーボネート等が反応性の点で好ましく用いられる。
[Compound (c4) having two or more oxygen or hetero groups other than oxygen]
Examples of the compound (c4) having two or more oxygen or hetero groups other than oxygen include a cyclic ester compound, a cyclic formal compound, a cyclic carbonate compound, and a fluorine-containing cyclic compound. The cyclic formal compound is preferably a compound selected from dioxolanes, dioxanes and trioxanes.
Industrially, propiolactone, caprolactone, 1,3-dioxolane, 1,2-dioxane, 1,4-dioxane, ethylene carbonate, propylene carbonate, glycerin carbonate and the like are preferably used in terms of reactivity.
カチオン重合性化合物(C)は、(c1)、(c2)、(c3)および(c4)が挙げられ、特に限定するものではないが、エポキシ基含有化合物(c1)、あるいはオキセタニル基含有化合物(c2)が好ましい。また、エポキシ基含有化合物(c1)、あるいはオキセタニル基含有化合物(c2)は、立体歪みが大きく、求核的開環反応を起こしやすい。そのため、重合時に架橋密度の向上が図れるため、凝集力が向上し易く、工業的にも好ましい。これらは使用目的によって、単独で用いてもよいし、2種類以上を併用してもよい。 Examples of the cationically polymerizable compound (C) include (c1), (c2), (c3) and (c4), and are not particularly limited, but include an epoxy group-containing compound (c1) or an oxetanyl group-containing compound ( c2) is preferred. In addition, the epoxy group-containing compound (c1) or the oxetanyl group-containing compound (c2) has a large steric distortion and tends to cause a nucleophilic ring-opening reaction. Therefore, since the crosslinking density can be improved at the time of polymerization, the cohesive force is easily improved, which is industrially preferable. These may be used alone or in combination of two or more depending on the purpose of use.
<活性エネルギー線重合開始剤(E)>
本発明に用いる重合性組成物は、各種活性化エネルギー線の照射によって重合反応が進行し、硬化可能である。しかし、上記重合性組成物は、必要に応じて活性エネルギー線重合開始剤(E) (以下「開始剤(E)」と略記することがある)を含んでもよい。開始剤(E)を使用することによって、重合反応を促進することができる。本発明の一実施形態において、上記活性化エネルギーは紫外線であることが好ましく、紫外線の照射によって重合反応を進行させる場合、重合性組成物は、開始剤(E)を含むことが好ましい。
<Active energy ray polymerization initiator (E)>
The polymerizable composition used in the present invention is curable by a polymerization reaction that proceeds by irradiation with various activation energy rays. However, the polymerizable composition may contain an active energy ray polymerization initiator (E) (hereinafter sometimes abbreviated as “initiator (E)”) as necessary. By using the initiator (E), the polymerization reaction can be accelerated. In one embodiment of the present invention, the activation energy is preferably ultraviolet rays, and when the polymerization reaction is allowed to proceed by irradiation with ultraviolet rays, the polymerizable composition preferably contains an initiator (E).
特に限定するものではないが、本発明の好ましい一実施形態において、活性エネルギー線を用いた硬化系の中でも、光ラジカル硬化系を用いる事が好ましい。その理由として、光ラジカル硬化系は、その他光硬化系と比較して格段に反応が速い事、下記光ラジカル発生剤(e1)や反応性材料である(メタ)アクリレートが容易にかつ安価に様々な種類が入手可能である事が挙げられる。 Although not particularly limited, in a preferred embodiment of the present invention, it is preferable to use a photo-radical curing system among the curing systems using active energy rays. The reason for this is that the photo-radical curing system has a much faster reaction than other photo-curing systems, and the following photo radical generator (e1) and (meth) acrylate, which is a reactive material, can be easily and inexpensively varied. Are available.
本発明では、開始剤(E)として、活性エネルギー線重合開始剤として公知の化合物から任意に選択した化合物を使用できる。 In the present invention, as the initiator (E), a compound arbitrarily selected from compounds known as active energy ray polymerization initiators can be used.
開始剤(E)のうち、光ラジカル発生剤(e1)としては、例えば、2,2−ジメトキシ−2−フェニルアセトフェノン、アセトフェノン、ベンゾフェノン、キサントフルオレノン、ベンズアルデヒド、アントラキノン、3−メチルアセトフェノン、4−クロロベンゾフェノン、4,4’−ジアミノベンゾフェノン、ベンゾインプロピルエーテル、ベンゾインエチルエーテル、ベンジルジメチルケタール、1−(4−イソプロピルフェニル)−2−ヒドロキシ−2−メチルプロパン−1−オン、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、4−チオキサントン、カンファーキノン、及び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−オン等が挙げられる。 Among the initiators (E), examples of the photo radical generator (e1) include 2,2-dimethoxy-2-phenylacetophenone, acetophenone, benzophenone, xanthfluorenone, benzaldehyde, anthraquinone, 3-methylacetophenone, 4- Chlorobenzophenone, 4,4′-diaminobenzophenone, benzoinpropyl ether, benzoin ethyl ether, benzyldimethyl ketal, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 2-hydroxy-2 -Methyl-1-phenylpropan-1-one, 4-thioxanthone, camphorquinone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one and the like.
また、市販品としては、例えば、イルガキュアー184,907,651,1700,1800,819,369,及び261(BASF社製)、DAROCUR−TPO(BASF社製、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)、ダロキュア−1173(メルク社製)、エザキュアーKIP150,及びTZT(日本シイベルヘグナー社製)、カヤキュアBMS,及びカヤキュアDMBI(日本化薬社製) 等が挙げられる。 Examples of commercially available products include Irgacure 184,907,651,1700,1800,819,369, and 261 (manufactured by BASF), DAROCUR-TPO (manufactured by BASF, 2,4,6-trimethylbenzoyl- Diphenyl-phosphine oxide), Darocur-1173 (manufactured by Merck), Ezacure KIP150, and TZT (manufactured by Nippon Shibel Hegner), Kayacure BMS, Kayacure DMBI (manufactured by Nippon Kayaku Co., Ltd.) and the like.
また、カチオン重合性化合物(C)やエポキシ変性植物油をカチオン重合性化合物として使用した場合には、開始剤(E)のうち、光酸発生剤(e2) を含有することが好ましい。光酸発生剤(e2)としては、例えば、UVACURE1590(ダイセル・サイテック社製)、CPI−110P(サンアプロ社製)、などのスルホニウム塩やIRGACURE250(BASFジャパン社製)、WPI−113(和光純薬工業社製)、RP−2074(ローディア・ジャパン社製)等のヨードニウム塩などに例示されるものが挙げられ、併用する事で重合架橋が進み、熱や湿度に対する耐久性に優れる硬化物を形成するため好ましい。 Further, when the cationically polymerizable compound (C) or the epoxy-modified vegetable oil is used as the cationically polymerizable compound, it is preferable to include the photoacid generator (e2) in the initiator (E). Examples of the photoacid generator (e2) include sulfonium salts such as UVACURE1590 (manufactured by Daicel Cytec), CPI-110P (manufactured by San Apro), IRGACURE250 (manufactured by BASF Japan), and WPI-113 (Wako Pure Chemical). Kogyo Co., Ltd.), RP-2074 (manufactured by Rhodia Japan Co., Ltd.), and other examples include iodonium salts. By using these in combination, polymerization crosslinking proceeds and forms a cured product with excellent durability against heat and humidity Therefore, it is preferable.
本発明では、開始剤(E)として、上述の化合物を単独で、又は2種類以上組合せて使用することができる。開始剤(E)の配合割合は、反応性の観点から、重合性組成物の総量を100質量部として、好ましくは0.01〜20質量部の範囲、より好ましくは0.5〜10質量部の範囲である。 In this invention, the above-mentioned compound can be used individually or in combination of 2 or more types as an initiator (E). The mixing ratio of the initiator (E) is preferably in the range of 0.01 to 20 parts by mass, more preferably 0.5 to 10 parts by mass, with the total amount of the polymerizable composition as 100 parts by mass, from the viewpoint of reactivity. Range.
本発明の重合性組成物は、実質的に有機溶剤を含まない。重合性組成物は、有機溶剤を全く含まないことが好ましいが、開始剤(E)は重合性成分に難溶性のことが多い。そのため、開始剤(E)を溶解するため少量の有機溶剤は含んでもよい。重合性組成物の総量を100質量部として、有機溶剤の含有量は5質量部以内であることが好ましい。 The polymerizable composition of the present invention does not substantially contain an organic solvent. The polymerizable composition preferably contains no organic solvent at all, but the initiator (E) is often poorly soluble in the polymerizable component. Therefore, a small amount of an organic solvent may be included to dissolve the initiator (E). The total amount of the polymerizable composition is 100 parts by mass, and the content of the organic solvent is preferably within 5 parts by mass.
更に、開始剤(E)の性能を向上させるために、活性エネルギー線増感剤を併用しても良い。活性エネルギー線増感剤としては、代表的なものを例記すれば、ベンゾフェノン誘導体、カルコン誘導体やジベンザルアセトン等に代表される不飽和ケトン誘導体、ベンジルやカンファーキノンなどに代表される1,2−ジケトン誘導体、ベンゾイン誘導体、フルオレン誘導体、ナフトキノン誘導体、アントラキノン誘導体、キサンテン誘導体、チオキサンテン誘導体、キサントン誘導体、チオキサントン誘導体、クマリン誘導体、ケトクマリン誘導体、シアニン誘導体、メロシアニン誘導体、オキソノ−ル誘導体等のポリメチン色素、アクリジン誘導体、アジン誘導体、チアジン誘導体、オキサジン誘導体、インドリン誘導体、アズレン誘導体、アズレニウム誘導体、スクアリリウム誘導体、ポルフィリン誘導体、テトラフェニルポルフィリン誘導体、トリアリールメタン誘導体、テトラベンゾポルフィリン誘導体、テトラピラジノポルフィラジン誘導体、フタロシアニン誘導体、テトラアザポルフィラジン誘導体、テトラキノキサリロポルフィラジン誘導体、ナフタロシアニン誘導体、サブフタロシアニン誘導体、ピリリウム誘導体、チオピリリウム誘導体、テトラフィリン誘導体、アヌレン誘導体、スピロピラン誘導体、スピロオキサジン誘導体、チオスピロピラン誘導体、金属アレーン錯体、有機ルテニウム錯体などが挙げられ、その他さらに具体例には大河原信ら編、「色素ハンドブック」(1986年、講談社)、大河原信ら編、「機能性色素の化学」(1981年、シーエムシー)、池森忠三朗ら編、「特殊機能材料」(1986年、シーエムシー)に記載の色素および増感剤が挙げられるがこれらに限定されるものではなく、その他、紫外から近赤外域にかけての光に対して吸収を示す色素や増感剤が挙げられ、これらは必要に応じて任意の比率で二種以上用いてもかまわない。 Furthermore, in order to improve the performance of the initiator (E), an active energy ray sensitizer may be used in combination. As typical examples of the active energy ray sensitizer, benzophenone derivatives, unsaturated ketone derivatives typified by chalcone derivatives and dibenzalacetone, benzyl and camphorquinone, etc. Polymethine dyes such as 2-diketone derivatives, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives, xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives , Acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, azulene derivatives, azurenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphy Derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives , Tetraphylline derivatives, annulene derivatives, spiropyran derivatives, spirooxazine derivatives, thiospiropyran derivatives, metal arene complexes, organoruthenium complexes and the like. Other specific examples include Okawara Shin et al., “Dye Handbook” (1986, Kodansha), Nobu Okawara et al., "Chemicals of Functional Dyes" (1981, CMC), Chusaburo Ikemori et al., "Special Functional Materials" (1986, CMC) However, it is not limited to these, and other dyes and sensitizers that absorb light from the ultraviolet to the near-infrared region are included, and these may be used in any ratio as necessary. The above may be used.
上記、増感剤の中でチオキサントン誘導体としては、2,4−ジエチルチオキサントン、2−クロロチオキサントン、2,4−ジクロロチオキサントン、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、1−クロロ−4−プロポキシチオキサントン等を挙げることができ、ベンゾフェノン類としては、ベンゾフェノン、4−メチルベンゾフェノン、2,4,6−トリメチルベンゾフェノン、4,4'−ジメチルベンゾフェノン、4,4'−ジメトキシベンゾフェノン、4,4'−ビス(ジエチルアミノ)ベンゾフェノン等を挙げることができ、クマリン類としては、クマリン1、クマリン338、クマリン102等を挙げることができ、ケトクマリン類としては、3,3'−カルボニルビス(7−ジエチルアミノクマリン)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。 Among the sensitizers, thioxanthone derivatives include 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propoxythioxanthone. Examples of benzophenones include benzophenone, 4-methylbenzophenone, 2,4,6-trimethylbenzophenone, 4,4′-dimethylbenzophenone, 4,4′-dimethoxybenzophenone, 4,4′-bis. (Diethylamino) benzophenone and the like can be mentioned. Examples of coumarins include coumarin 1, coumarin 338 and coumarin 102. Examples of ketocoumarins include 3,3′-carbonylbis (7-diethylaminocoumarin). Raised Although it is Rukoto, but is not limited thereto.
<シラン化合物(F)>
本発明の重合性組成物には、シラン化合物(F)を含んでもよい。シラン化合物(F)としては、公知のシラン化合物を用いることができる。例えば、テトラメトキシシラン、テトラエトキシシラン、メチルプロピルジイソプロポキシシラン、メチルプロピルジアセトキシシラン、等のアルキル系アルコキシシラン類;
<Silane compound (F)>
The polymerizable composition of the present invention may contain a silane compound (F). A known silane compound can be used as the silane compound (F). For example, alkyl alkoxysilanes such as tetramethoxysilane, tetraethoxysilane, methylpropyldiisopropoxysilane, methylpropyldiacetoxysilane, etc .;
例えば、フェニルトリメトキシシラン、フェニルトリエトキシシラン、フェニルトリイソプロポキシシラン、フェニルトリアセトキシシラン、トリルトリメトキシシラン、トリルトリエトキシシラン、ジフェニルジメトキシシラン、ジフェニルジエトキシシラン、ジフェニルジイソプロポキシシラン、ジフェニルジアセトキシシラン、メチルフェニルジメトキシシラン、メチルフェニルジエトキシシラン、メチルフェニルジイソプロポキシシラン、メチルフェニルジアセトキシシラン等のアリール系アルコキシシラン類; For example, phenyltrimethoxysilane, phenyltriethoxysilane, phenyltriisopropoxysilane, phenyltriacetoxysilane, tolyltrimethoxysilane, tolyltriethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, diphenyldiisopropoxysilane, diphenyldi Aryl alkoxysilanes such as acetoxysilane, methylphenyldimethoxysilane, methylphenyldiethoxysilane, methylphenyldiisopropoxysilane, methylphenyldiacetoxysilane;
例えば、ジメトキシメチルシラン、トリス(ジメチルアミノ)シラン等が挙げられる。 Examples thereof include dimethoxymethylsilane and tris (dimethylamino) silane.
また、シラン化合物(F)としては市販製品を用いることも可能であるし、2種以上のシラン混合物を加水分解・縮合してオリゴマー化したオリゴマー系シランを使用する事もこれらシラン化合物(F)に含まれる。該シラン化合物(F)は単独または2種類以上の混合物として使用することも可能である。 Moreover, it is also possible to use a commercial product as the silane compound (F), and it is also possible to use an oligomeric silane obtained by oligomerizing a mixture of two or more silanes by hydrolysis and condensation. include. The silane compound (F) can be used alone or as a mixture of two or more.
<酸化防止剤(G)>
本発明における重合性組成物は、更に酸化防止剤を含んでも良い。酸化防止剤(G)を含むことによって、活性エネルギー線重合後の樹脂硬化物の経時での着色を抑制することができる。
酸化防止剤としては、例えば、アデカスタブAO‐50、アデカスタブAO‐80(アデカ社製)などのフェノール系酸化防止剤や、アデカスタブPEP−8(アデカ社製)、IRGAFOS168(BASF社製)などのリン系酸化防止剤、IRGANOX‐PS‐800FD(BASF社製)などのイオウ系酸化防止剤等の市販品が挙げられるが、これらに限定されるものではない。
<Antioxidant (G)>
The polymerizable composition in the present invention may further contain an antioxidant. By containing the antioxidant (G), coloring of the cured resin after active energy ray polymerization over time can be suppressed.
Examples of the antioxidant include phenolic antioxidants such as ADK STAB AO-50 and ADK STAB AO-80 (manufactured by ADEKA), phosphorus such as ADK STAB PEP-8 (manufactured by ADEKA) and IRGAFOS 168 (manufactured by BASF). Commercially available products such as sulfur-based antioxidants such as sulfur-based antioxidants and IRGANOX-PS-800FD (manufactured by BASF) are not limited thereto.
<色材(J)>
本発明の重合性組成物は、上記成分に加えて、色材(J)を含有しても良い。本発明において、色材(J)は、染料や顔料が分散された材料の総称である。色材(J) を使用することによって、含有される染料や顔料によって、意匠性だけで無く、熱特性、電気特性、あるいは光学特性等の様々な機能性を付与することが可能となる。
<Coloring material (J)>
The polymerizable composition of the present invention may contain a color material (J) in addition to the above components. In the present invention, the color material (J) is a general term for materials in which dyes and pigments are dispersed. By using the coloring material (J), it is possible to impart not only design properties but also various functionalities such as thermal properties, electrical properties, and optical properties, depending on the dyes and pigments contained therein.
色材(J)は、染料や顔料を分散樹脂で高濃度に分散させて使用される。このような染料や顔料としては、例えば、カーボンブラック、酸化チタン、炭酸カルシウム等の無彩色の顔料または有彩色の有機顔料や染料が使用できる。
例えば、有機顔料としては、トルイジンレッド、トルイジンマルーン、ハンザエロー、ベンジジンエロー、ピラゾロンレッドなどの不溶性アゾ顔料、
リトールレッド、ヘリオボルドー、ピグメントスカーレット、パーマネントレッド2Bなどの溶性アゾ顔料、
アリザリン、インダントロン、チオインジゴマルーンなどの建染染料からの誘導体、
フタロシアニンブルー、フタロシアニングリーンなどのフタロシアニン系有機顔料、
キナクリドンレッド、キナクリドンマゼンタなどのキナクリドン系有機顔料、
ペリレンレッド、ペリレンスカーレットなどのペリレン系有機顔料、
イソインドリノンエロー、イソインドリノンオレンジなどのイソインドリノン系有機顔料、
ピランスロンレッド、ピランスロンオレンジなどのピランスロン系有機顔料、チオインジゴ系有機顔料、縮合アゾ系有機顔料、ベンズイミダゾロン系有機顔料、
キノフタロンエローなどのキノフタロン系有機顔料、
イソインドリンエローなどのイソインドリン系有機顔料、
その他の顔料として、フラバンスロンエロー、アシルアミドエロー、ニッケルアゾエロー、銅アゾメチンエロー、ペリノンオレンジ、アンスロンオレンジ、ジアンスラキノニルレッド、ジオキサジンバイオレット等の有機顔料類が挙げられる。
The coloring material (J) is used by dispersing a dye or pigment in a high concentration with a dispersing resin. As such dyes and pigments, for example, achromatic pigments such as carbon black, titanium oxide, and calcium carbonate, or chromatic organic pigments and dyes can be used.
Examples of organic pigments include insoluble azo pigments such as toluidine red, toluidine maroon, Hansa Yellow, Benzidine Yellow, and pyrazolone red,
Soluble azo pigments such as Ritolol Red, Helio Bordeaux, Pigment Scarlet, Permanent Red 2B,
Derivatives from vat dyes such as alizarin, indanthrone, thioindigo maroon,
Phthalocyanine organic pigments such as phthalocyanine blue and phthalocyanine green,
Quinacridone organic pigments such as quinacridone red and quinacridone magenta;
Perylene organic pigments such as perylene red and perylene scarlet,
Isoindolinone organic pigments such as isoindolinone yellow and isoindolinone orange;
Pyranthrone organic pigments such as pyranthrone red and pyranthrone orange, thioindigo organic pigments, condensed azo organic pigments, benzimidazolone organic pigments,
Quinophthalone organic pigments such as quinophthalone yellow,
Isoindoline organic pigments such as isoindoline yellow,
Other pigments include organic pigments such as Flavanthrone Yellow, Acylamide Yellow, Nickel Azo Yellow, Copper Azomethine Yellow, Perinone Orange, Anthrone Orange, Dianthraquinonyl Red, Dioxazine Violet.
例えば、染料としては、アゾ系染料、ローダミン系染料、キノリン系染料、チアジン系染料、チアゾール系染料、キサンテン系染料、ニグロシン染料等が挙げられる。
これら色素誘導体であれば、特に問題無く使用できる。
Examples of the dye include azo dyes, rhodamine dyes, quinoline dyes, thiazine dyes, thiazole dyes, xanthene dyes, and nigrosine dyes.
These dye derivatives can be used without any particular problem.
色材(J)を分散させるための分散剤のうち、分散樹脂としては、一般的なアクリル系樹脂が使用され、場合によっては界面活性剤や上記の化合物(A)等も併用使用される。上記アクリル系樹脂は、ラジカル重合可能な骨格やカチオン重合可能な骨格を有しておらず、化合物(A)には含まれない。
分散樹脂は、染料や顔料100質量部に対し、不揮発分換算で10〜60質量部の範囲で使用する事が好ましい。また、化合物(A)を併用する場合には、染料や顔料100質量部に対し、不揮発分換算で100〜800質量部の範囲で使用する事が好ましい。
Of the dispersants for dispersing the colorant (J), a general acrylic resin is used as the dispersion resin, and in some cases, a surfactant, the above-described compound (A), or the like is also used in combination. The acrylic resin does not have a skeleton capable of radical polymerization or a skeleton capable of cationic polymerization, and is not included in the compound (A).
The dispersion resin is preferably used in the range of 10 to 60 parts by mass in terms of non-volatile content with respect to 100 parts by mass of the dye or pigment. Moreover, when using a compound (A) together, it is preferable to use in 100-800 mass parts in conversion of a non volatile matter with respect to 100 mass parts of dyes and pigments.
染料や顔料の分散安定化のために、必要に応じて極性樹脂を使用することも可能である。
このような極性樹脂としては、例えば、ポリビニルアルコール、ポリビニルピロリドン、ポリエチレングリコール、ポリ(メタ)アクリル酸、(メタ)アクリル酸−(メタ)アクリル酸アルキルエステル共重合体、スチレン−マレイン酸共重合体、スチレン−マレイン酸−(メタ)アクリル酸アルキルエステル共重合体、酢酸ビニル−クロトン酸共重合体、酢酸ビニル−(メタ)アクリル酸共重合体、ポリスチレンスルホン酸、ポリスチレンスルホン酸ナトリウム、スチレンスルホン酸−マレイン酸共重合体、ポリイタコン酸等の親水性のビニル系共重合体樹脂;
In order to stabilize the dispersion of dyes and pigments, polar resins can be used as necessary.
Examples of such polar resins include polyvinyl alcohol, polyvinyl pyrrolidone, polyethylene glycol, poly (meth) acrylic acid, (meth) acrylic acid- (meth) acrylic acid alkyl ester copolymers, and styrene-maleic acid copolymers. , Styrene-maleic acid- (meth) acrylic acid alkyl ester copolymer, vinyl acetate-crotonic acid copolymer, vinyl acetate- (meth) acrylic acid copolymer, polystyrene sulfonic acid, sodium polystyrene sulfonate, styrene sulfonic acid -Hydrophilic vinyl copolymer resins such as maleic acid copolymer and polyitaconic acid;
例えば、多価カルボン酸とポリオールの重縮合反応により得られるポリエステル樹脂であり、極性基の導入により樹脂全体が極性/非極性のバランスをとられたポリエステル樹脂;
メチルセルロース、エチルセルロース、プロピルセルロース、エチルメチルセルロース、ヒドロキシアルキルセルロース、ヒドロキシプロピルメチルセルロース、カルボシキメチルスセルロース、アルカリ金属カルボキシメチルセルロース、アルカリ金属セルロース硫酸塩、セルロースグラフト重合体等のセルロース誘導体;
ポリグルタミン酸、ポリアスパラギン酸等のポリペプチド類;
長鎖ポリアミノアマイドと極性酸エステルの塩、長鎖ポリアミノアマイドと高分子量酸エステルの塩、ナフタレンスルホン酸ホルマリン縮合物塩、ステアリルアミンアセテート等のアミドエステル塩;
等が挙げられるが、特にこれらに限定されるものではない。これらは1種類または2種以上を併用して用いることができる。
For example, a polyester resin obtained by a polycondensation reaction of a polyvalent carboxylic acid and a polyol, and the entire resin is balanced in polarity / nonpolarity by introducing a polar group;
Cellulose derivatives such as methyl cellulose, ethyl cellulose, propyl cellulose, ethyl methyl cellulose, hydroxyalkyl cellulose, hydroxypropyl methyl cellulose, carboxymethyl cellulose, alkali metal carboxymethyl cellulose, alkali metal cellulose sulfate, cellulose graft polymer;
Polypeptides such as polyglutamic acid and polyaspartic acid;
Amide ester salts such as salts of long chain polyaminoamides and polar acid esters, salts of long chain polyaminoamides and high molecular weight acid esters, naphthalenesulfonic acid formalin condensates, stearylamine acetate, etc .;
However, it is not particularly limited to these. These can be used alone or in combination of two or more.
分散樹脂として市販されている極性樹脂としては、例えば、アビシア社製「Anti−Terra−U(ポリアミノアマイド燐酸塩)」、「Anti−Terra−203/204(高分子量ポリカルボン酸塩)」、「Disperbyk−101(ポリアミノアマイド燐酸塩と酸エステル)、107(水酸基含有カルボン酸エステル)、110、111(酸基を含む共重合物)、130(ポリアマイド)、161、162、163、164、165、166、170(高分子共重合物)」、「400」、「Bykumen」(高分子量不飽和酸エステル)、「BYK−P104、P105(高分子量不飽和酸ポリカルボン酸)」、「P104S、240S(高分子量不飽和酸ポリカルボン酸とシリコン系)」、「Lactimon(長鎖アミンと不飽和酸ポリカルボン酸とシリコン)」が挙げられる。
また、Efka CHEMICALS社製「エフカ44、46、47、48、49、54、63、64、65、66、71、701、764、766」、「エフカポリマー100(変性ポリアクリレート)、150(脂肪族系変性ポリマー)、400、401、402、403、450、451、452、453(変性ポリアクリレート)、745(銅フタロシアニン系)」、共栄社化学社製「フローレン TG−710(ウレタンオリゴマー)、「フローノンSH−290、SP−1000」、「ポリフローNo.50E、No.300(アクリル系共重合物)」、楠本化成社製「ディスパロン KS−860、873SN、874(高分子分散剤)、#2150(脂肪族多価カルボン酸)、#7004(ポリエーテルエステル型)」が挙げられる。
Examples of polar resins that are commercially available as dispersion resins include “Anti-Terra-U (polyaminoamide phosphate)”, “Anti-Terra-203 / 204 (high molecular weight polycarboxylate)” manufactured by Avicia, Disperbyk-101 (polyaminoamide phosphate and acid ester), 107 (hydroxyl group-containing carboxylic acid ester), 110, 111 (copolymer containing an acid group), 130 (polyamide), 161, 162, 163, 164, 165, 166, 170 (high molecular weight copolymer) "," 400 "," Bykumen "(high molecular weight unsaturated acid ester)," BYK-P104, P105 (high molecular weight unsaturated acid polycarboxylic acid) "," P104S, 240S " (High molecular weight unsaturated acid polycarboxylic acid and silicon system) ”,“ Lactimon (long chain amine and unsaturated acid polycarboxylic acid) Silicon) ", and the like.
Further, “Efka CHEMICALS” “Efka 44, 46, 47, 48, 49, 54, 63, 64, 65, 66, 71, 701, 764, 766”, “Efka Polymer 100 (modified polyacrylate), 150 (aliphatic) System modified polymer), 400, 401, 402, 403, 450, 451, 452, 453 (modified polyacrylate), 745 (copper phthalocyanine system) "," Floren TG-710 (urethane oligomer), "Flownon manufactured by Kyoeisha Chemical Co., Ltd. “SH-290, SP-1000”, “Polyflow No. 50E, No. 300 (acrylic copolymer)”, “Disparon KS-860, 873SN, 874 (polymer dispersing agent), # 2150, manufactured by Enomoto Kasei Co., Ltd. Aliphatic polycarboxylic acid), # 7004 (polyether ester type) ”.
<添加剤(Q)>
本発明の重合性組成物は、本発明の効果を損なわない範囲で有れば、前記したような成分の他に各種添加剤(Q)を適宜配合することが可能である。例えば、重合硬化収縮率低減、熱膨張率低減、寸法安定性向上、弾性率向上、粘度調整、熱伝導率向上、強度向上、靭性向上、着色向上等の観点から有機又は無機の充填剤を配合できる。このような充填剤としては、ポリマー、セラミックス、金属、金属酸化物、金属塩等を用いることができ、形状については粒子状、繊維状等特に限定されない。なお、上記ポリマーの配合に当っては、柔軟性付与剤、可塑剤、難燃化剤、保存安定剤、チクソトロピー付与剤、分散安定剤、流動性付与剤、消泡剤等、充填剤としてではなくポリマーブレンド、ポリマーアロイとして、重合性組成物中に溶解、半溶解又はミクロ分散させることも可能である。
<Additive (Q)>
If the polymerizable composition of the present invention is within a range that does not impair the effects of the present invention, it is possible to appropriately mix various additives (Q) in addition to the above-described components. For example, blending organic or inorganic fillers from the viewpoints of polymerization cure shrinkage reduction, thermal expansion coefficient reduction, dimensional stability improvement, elastic modulus improvement, viscosity adjustment, thermal conductivity improvement, strength improvement, toughness improvement, coloring improvement, etc. it can. As such a filler, polymers, ceramics, metals, metal oxides, metal salts, and the like can be used, and the shape is not particularly limited, such as particles and fibers. In addition, in the blending of the above polymer, as a filler, such as a flexibility imparting agent, a plasticizer, a flame retardant, a storage stabilizer, a thixotropy imparting agent, a dispersion stabilizer, a fluidity imparting agent, an antifoaming agent, etc. Alternatively, it can be dissolved, semi-dissolved or micro-dispersed in the polymerizable composition as a polymer blend or polymer alloy.
<活性エネルギー線重合性組成物の製造>
本発明に用いる重合性組成物は、必要に応じて、上記、化合物(A)、化合物(B)、化合物(C)、開始剤(E)、シラン化合物(F)、酸化防止剤(G)、色材(J)およびその他の各種添加剤(Q)を配合後、均一に混合することによって製造することができる。
<Manufacture of an active energy ray polymerizable composition>
The polymerizable composition used in the present invention may contain, as necessary, the above compound (A), compound (B), compound (C), initiator (E), silane compound (F), and antioxidant (G). The colorant (J) and other various additives (Q) can be mixed and then mixed uniformly.
本発明における活性エネルギー線重合性組成物は、重合性組成物全量100質量%中、化合物(A)を50〜100質量%含有することが好ましく、化合物(A)を50〜80質量%含有することが更に好ましい。重合性組成物全量100質量%中、化合物(A)が、50質量%以上であれば、架橋密度の向上が期待でき、ハードコート性に優れた硬化物を得ることを期待できる。 The active energy ray polymerizable composition in the present invention preferably contains 50 to 100% by mass of the compound (A) in 100% by mass of the total amount of the polymerizable composition, and contains 50 to 80% by mass of the compound (A). More preferably. If the compound (A) is 50% by mass or more in 100% by mass of the total amount of the polymerizable composition, an improvement in the crosslinking density can be expected, and a cured product having excellent hard coat properties can be expected.
重合性組成物を攪拌・混合する際には、減圧装置を備えた1軸または多軸エクストルーダー、ニーダー、ディソルバーのような汎用の機器を使用し、攪拌・混合することにより調製してもよい。攪拌・混合する際の温度は、通常、10〜60℃に設定されるのが好ましい。 When the polymerizable composition is stirred and mixed, it may be prepared by stirring and mixing using a general-purpose device such as a uniaxial or multiaxial extruder, kneader, or dissolver equipped with a decompression device. Good. Usually, the temperature at the time of stirring and mixing is preferably set to 10 to 60 ° C.
以下に、本発明の具体的な実施例を比較例と併せて説明するが、本発明は、下記実施例に限定されない。また、特に断りのない限り、実施例および比較例中、「部」および「%」は、それぞれ「質量部」および「質量%」を表す。 Specific examples of the present invention will be described below together with comparative examples, but the present invention is not limited to the following examples. Unless otherwise specified, “parts” and “%” in Examples and Comparative Examples represent “parts by mass” and “% by mass”, respectively.
<色材(J)分散体の製造>
[製造例1、2]
活性エネルギー線重合性組成物と分散樹脂とを攪拌し、分散樹脂が完全に溶解したことを確認した後、顔料を投入し、ハイスピードミキサー等で均一になるまで攪拌後、得られたミルベースを横型サンドミルで約2時間分散して製造した。製造した色材(J)の分散体(顔料分散体)の配合(数値は質量部を表す)を表1に示す。表1において、空欄は、配合なしを意味している。
<Manufacture of colorant (J) dispersion>
[Production Examples 1 and 2]
After stirring the active energy ray polymerizable composition and the dispersion resin, and confirming that the dispersion resin is completely dissolved, the pigment is added, and the resulting mill base is stirred until it becomes uniform with a high speed mixer or the like. It was produced by dispersing for about 2 hours in a horizontal sand mill. Table 1 shows the composition of the dispersion (pigment dispersion) of the produced coloring material (J) (the numerical value represents parts by mass). In Table 1, a blank means no blending.
<実施例> <Example>
[実施例1〜42][比較例1〜8]
<重合性組成物の製造>
[配合例1〜21]
酸素濃度が10%以下に置換された遮光された300mlのガラス瓶に、活性エネルギー線重合性組成物を表2に示す比率で仕込み、攪拌機にて十分に攪拌を行い、十分に脱泡を行った後、配合例に示す重合性組成物を得た。尚、表2において、空欄は、配合なしを表す。表2で使用した略号の説明を、表3に示す。
[Examples 1-42] [Comparative Examples 1-8]
<Production of polymerizable composition>
[Composition Examples 1 to 21]
The active energy ray polymerizable composition was charged in a light-shielded 300 ml glass bottle substituted with an oxygen concentration of 10% or less at a ratio shown in Table 2, and sufficiently agitated with a stirrer to sufficiently degas. Thereafter, a polymerizable composition shown in the formulation example was obtained. In Table 2, the blank represents no blending. Table 3 shows the abbreviations used in Table 2.
<重合性組成物および硬化物の評価>
表2に示した重合性組成物について、以下の方法で硬化物を製造するとともに、硬化速度、鉛筆硬度、及び耐擦傷性を測定し、評価を行った。評価結果を表4に示す。
<Evaluation of polymerizable composition and cured product>
About the polymeric composition shown in Table 2, while manufacturing hardened | cured material with the following method, hardening rate, pencil hardness, and scratch resistance were measured, and evaluation was performed. The evaluation results are shown in Table 4.
《硬化速度》
アプリケータを用いて、ポリエチレンテレフタレート(PET)フィルム上に重合性組成物を塗布膜厚が10μm厚となるように塗布し、塗布後のPETフィルムを表4に示す温度に設定したフィルムシートヒーター(FSHH型、(株)東京技術研究所社製)上に設置し、0.3J/cm2(波長 :365nm)の紫外線を照射して、硬化フィルムを作製した。照射後の硬化物の表面を指触により、べたつきがなくなるまで照射を繰り返し、べたつきがなくなるまでの照射時間の合計を測定することにより硬化速度を3段階で評価した。べたつきがなくなるまでの照射時間の合計が短いほど硬化性が良好であると判断できる。評価「×」以外であれば、実際の使用時に特に問題ない。
○:11.0秒未満。全く問題なし。
△:11.0秒以上17.0秒未満。実用上、使用可。
×:17.0秒以上。実用上、問題あり。
《Curing speed》
Using an applicator, a film sheet heater (on which a polymerizable composition was applied on a polyethylene terephthalate (PET) film so that the applied film thickness was 10 μm, and the PET film after application was set to the temperature shown in Table 4) FSHH type (manufactured by Tokyo Institute of Technology, Inc.) was irradiated with ultraviolet rays of 0.3 J / cm 2 (wavelength: 365 nm) to prepare a cured film. The surface of the cured product after irradiation was touched with a finger until the stickiness disappeared, and the curing speed was evaluated in three stages by measuring the total irradiation time until stickiness disappeared. It can be judged that the curability is better as the total irradiation time until stickiness disappears is shorter. Other than the evaluation “x”, there is no problem in actual use.
○: Less than 11.0 seconds. No problem at all.
Δ: 11.0 seconds or more and less than 17.0 seconds. Can be used practically.
X: 17.0 seconds or more. There is a problem in practical use.
《鉛筆硬度》
アプリケータを用いてPETフィルム上に重合性組成物を塗布膜厚が10μm 厚となるように塗布し、塗布後のPETフィルムを任意の温度に設定したフィルムシートヒーター(FSHH型、(株)東京技術研究所社製)上に設置し、0.3J/cm2(波長 :365nm)の紫外線を照射して硬化フィルムを得、23℃、相対湿度50%で24時間状態保存し、試験片とした。23℃、相対湿度50%の恒温湿室内で、クレメンス型引掻き硬度試験機(型式:HA−301テスター産業社製)を用いてJIS K 5600−5−4に準拠し、荷重750gf(7.35N)にて測定を行った。
評価は3段階で行った。硬い鉛筆でも傷が入らない方が、ハードコート性が良好であると判断できる。評価「×」以外であれば、実際の使用時に特に問題ない。
○:5H以上。全く問題なし。
△:3H〜4H。実用上、使用可。
×:2H以下。実用上、問題あり。
"Pencil hardness"
A film sheet heater (FSHH type, Tokyo Co., Ltd.) in which a polymerizable composition is applied onto a PET film using an applicator so that the coating film thickness is 10 μm, and the PET film after application is set to an arbitrary temperature. Placed on the Technical Research Institute Co., Ltd.), irradiated with ultraviolet rays of 0.3 J / cm 2 (wavelength: 365 nm) to obtain a cured film, stored for 24 hours at 23 ° C. and 50% relative humidity, did. In accordance with JIS K 5600-5-4 using a Clemens type scratch hardness tester (model: manufactured by HA-301 Tester Sangyo Co., Ltd.) in a constant temperature and humidity room at 23 ° C. and 50% relative humidity, a load of 750 gf (7.35 N) ).
Evaluation was performed in three stages. It can be judged that the hard coat property is better when a hard pencil is not damaged. Other than the evaluation “x”, there is no problem in actual use.
○: 5H or more. No problem at all.
Δ: 3H-4H. Can be used practically.
X: 2H or less. There is a problem in practical use.
《耐擦傷性》
アプリケータを用いてPETフィルム上に重合性組成物を塗布膜厚が10μm 厚となるように塗布し、塗布後のPETフィルムを任意の温度に設定したフィルムシートヒーター(FSHH型、(株)東京技術研究所社製)上に設置し、0.3J/cm2(波長 :365nm)の紫外線を照射して硬化フィルムを得、23℃、相対湿度50%で24時間状態保存し、試験片とした。23℃、相対湿度50%の恒温湿室内で、前記試験片を#0000のスチールウールにより、硬化フィルムの表面を1cm2当たり250gf(2.45N)の荷重をかけながら10回摩擦し、耐擦傷性試験を行った。傷の発生の有無および傷の程度を目視により観察し、耐擦傷性の指標とした。
評価は3段階で行った。傷の本数が少ないほど耐擦傷性が良好であると判断できる。評価「×」以外であれば、実際の使用時に特に問題ない。
○:傷の発生なし。全く問題なし。
△:5本以下の傷が発生する。実用上、使用可。
×:傷が6本以上発生する。実用上、問題あり。
《Abrasion resistance》
A film sheet heater (FSHH type, Tokyo Co., Ltd.) in which a polymerizable composition is applied onto a PET film using an applicator so that the coating film thickness is 10 μm, and the PET film after application is set to an arbitrary temperature. Placed on the Technical Research Institute Co., Ltd.), irradiated with ultraviolet rays of 0.3 J / cm 2 (wavelength: 365 nm) to obtain a cured film, stored for 24 hours at 23 ° C. and 50% relative humidity, did. In a constant temperature and humidity chamber at 23 ° C. and a relative humidity of 50%, the test piece was rubbed 10 times with # 0000 steel wool while applying a load of 250 gf (2.45 N) per cm 2 to the surface of the cured film, thereby being scratch-resistant. A sex test was performed. The presence or absence of scratches and the degree of scratches were visually observed and used as an index of scratch resistance.
Evaluation was performed in three stages. It can be judged that the smaller the number of scratches, the better the scratch resistance. Other than the evaluation “x”, there is no problem in actual use.
○: No scratch was generated. No problem at all.
Δ: 5 or less scratches occur. Can be used practically.
X: Six or more scratches occur. There is a problem in practical use.
表4において、「硬化速度」は重合速度を評価している。重合速度が遅く、未反応の二重結合が組成物中に多く存在すると、光照射後にも膜にべたつきが残る。「鉛筆硬度」および「耐擦傷性」は硬化物表面の硬度を評価している。 In Table 4, “curing speed” evaluates the polymerization speed. When the polymerization rate is slow and many unreacted double bonds are present in the composition, the film remains sticky even after light irradiation. “Pencil hardness” and “scratch resistance” evaluate the hardness of the surface of the cured product.
本発明の製造方法にて重合硬化させた場合は、表4に示すように優れた硬化速度を示し、かつ鉛筆硬度、耐擦傷性の全ての項目において優れた結果を示した(実施例1〜42)。これに対して、本発明以外の製造方法にて重合硬化させた場合は、硬化速度、鉛筆硬度、耐擦傷性のいずれかに難があり、使用困難であることがわかる。 When polymerized and cured by the production method of the present invention, an excellent curing rate was exhibited as shown in Table 4, and excellent results were shown in all items of pencil hardness and scratch resistance (Examples 1 to 1). 42). On the other hand, when polymerized and cured by a production method other than the present invention, it is difficult to use any of the curing speed, pencil hardness and scratch resistance.
本発明の製造方法にて重合硬化させた場合は、表4に示すように、硬化速度に優れ、かつ鉛筆硬度、耐擦傷性等のハードコート性に優れた硬化物を作製する事が可能である(実施例1〜実施例42)。
これに対して本発明とは異なる製造方法では、同じ重合組成物を使用したとしても十分なハードコート性を有する硬化物を迅速に得る事は出来ない(比較例1〜比較例8)。
When polymerized and cured by the production method of the present invention, as shown in Table 4, it is possible to produce a cured product having excellent curing speed and excellent hard coat properties such as pencil hardness and scratch resistance. (Examples 1 to 42).
On the other hand, in the production method different from the present invention, a cured product having sufficient hard coat properties cannot be obtained quickly even if the same polymerization composition is used (Comparative Examples 1 to 8).
Claims (5)
加熱処理によって活性エネルギー線重合性組成物を65℃以上とした状態で活性エネルギー線を照射することで、JIS K5600−5−4に基づく鉛筆硬度評価において5H以上の硬化度を発生させることを特徴とする硬化物の製造方法。 It is a method for producing a cured product that forms a cured product by irradiating an active energy ray polymerizable composition with an active energy beam,
A curing degree of 5H or more is generated in pencil hardness evaluation based on JIS K5600-5-4 by irradiating an active energy ray in a state where the active energy ray polymerizable composition is 65 ° C. or higher by heat treatment. A method for producing a cured product.
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JP2005288787A (en) * | 2004-03-31 | 2005-10-20 | Nippon Paper Industries Co Ltd | Hard coat film and its production method |
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JP2017517597A (en) * | 2014-04-22 | 2017-06-29 | サビック グローバル テクノロジーズ ベスローテン フェンノートシャップ | UV curable transfer coating for applying nanometer size metal particles to polymer surface |
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JPS50116579A (en) * | 1973-12-13 | 1975-09-11 | ||
JP2005182963A (en) * | 2003-12-24 | 2005-07-07 | Bridgestone Corp | Optical information recording medium, its manufacturing method, photocuring composition, and photocuring transfer sheet |
JP2005288787A (en) * | 2004-03-31 | 2005-10-20 | Nippon Paper Industries Co Ltd | Hard coat film and its production method |
JP2017517597A (en) * | 2014-04-22 | 2017-06-29 | サビック グローバル テクノロジーズ ベスローテン フェンノートシャップ | UV curable transfer coating for applying nanometer size metal particles to polymer surface |
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